Sonochemical Effects on 14 Flavonoids Common in Citrus: Relation to Stability

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Qiao, Liping; Sun, Yujing; Chen, Rongrong; Fu, Yu; Zhang, Wenjuan; Li, Xin; Chen, Jianchu; Shen, Yan; Ye, Xingqian

2014-01-01

The sonochemical effects of ultrasound (US) treatment on 14 flavonoids representing the main flavonoids in citrus fruit were investigated in a standard mixture by stability evaluation of a model system. Degradation products were further tentatively identified by Fourier transform infrared spectroscopy and high-performance liquid chromatography–ultraviolet detection–electrospray ionization tandem mass spectrometry. Thirteen flavonoids (i.e., eriocitrin, narirutin, neohesperidin, quercitrin, eridictyol, didymin, naringenin, luteolin, sinensetin, nobiletin, tangeretin, naringin, and hesperidin) were fairly stable whereas quercetin was degraded significantly by US treatment. The types of solvent and temperature used were important factors that determined the resulting degradation reactions. The degradation rate of quercetin was highest in 80% ethanol aqueous solution and decreased with increasing temperature. Longer US durations caused increases in the extent of quercetin degradation. Liquid height, ultrasonic intensity, pulse length, and duty cycle of US affected degradation rates but did not change the nature of degradation of the flavonoids. Four types of reactions occurred simultaneously for quercetin under US treatment: oxidation, addition, polymerization, and decomposition. Eight degradation products were tentatively identified as dimer, alcohol addition, oxidation, and decomposition products. PMID:24516562

De novo production of the flavonoid naringenin in engineered Saccharomyces cerevisiae

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Koopman Frank

2012-12-01

Full Text Available Abstract Background Flavonoids comprise a large family of secondary plant metabolic intermediates that exhibit a wide variety of antioxidant and human health-related properties. Plant production of flavonoids is limited by the low productivity and the complexity of the recovered flavonoids. Thus to overcome these limitations, metabolic engineering of specific pathway in microbial systems have been envisaged to produce high quantity of a single molecules. Result Saccharomyces cerevisiae was engineered to produce the key intermediate flavonoid, naringenin, solely from glucose. For this, specific naringenin biosynthesis genes from Arabidopsis thaliana were selected by comparative expression profiling and introduced in S. cerevisiae. The sole expression of these A. thaliana genes yielded low extracellular naringenin concentrations ( Conclusion The results reported in this study demonstrate that S. cerevisiae is capable of de novo production of naringenin by coexpressing the naringenin production genes from A. thaliana and optimization of the flux towards the naringenin pathway. The engineered yeast naringenin production host provides a metabolic chassis for production of a wide range of flavonoids and exploration of their biological functions.

Naringin prevents ovariectomy-induced osteoporosis and promotes osteoclasts apoptosis through the mitochondria-mediated apoptosis pathway

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Li, Fengbo [Tianjin Institute of Orthopedics in Traditional Chinese and Western Medicine, No. 155, Munan Road, Tianjin TJ 300050 (China); Graduate School of Tianjin Medical University, No. 22, Qixiangtai Street, Heping District, Tianjin 300070 (China); Sun, Xiaolei; Ma, Jianxiong [Tianjin Institute of Orthopedics in Traditional Chinese and Western Medicine, No. 155, Munan Road, Tianjin TJ 300050 (China); Ma, Xinlong, E-mail: gengxiao502@163.com [Tianjin Institute of Orthopedics in Traditional Chinese and Western Medicine, No. 155, Munan Road, Tianjin TJ 300050 (China); Zhao, Bin; Zhang, Yang; Tian, Peng [Tianjin Institute of Orthopedics in Traditional Chinese and Western Medicine, No. 155, Munan Road, Tianjin TJ 300050 (China); Li, Yanjun [Graduate School of Tianjin Medical University, No. 22, Qixiangtai Street, Heping District, Tianjin 300070 (China); Han, Zhe [Tianjin Institute of Orthopedics in Traditional Chinese and Western Medicine, No. 155, Munan Road, Tianjin TJ 300050 (China)

2014-09-26

Highlights: • Naringin possesses many pharmacological activities, promotes the proliferation of osteoblast. • Undecalcified histological obtain dynamic parameters of callus formation and remodeling. • Naringin regulate osteoclast apoptosis by mitochondrial pathway. - Abstract: Naringin, the primary active compound of the traditional Chinese medicine Rhizoma drynariae, possesses many pharmacological activities. The present study is an effort to explore the anti-osteoporosis potential of naringin in vivo and in vitro. In vivo, we used ovariectomized rats to clarify the mechanisms by which naringin anti-osteoporosis. In vitro, we used osteoclasts to investigate naringin promotes osteoclasts apoptosis. Naringin was effective at enhancing BMD, trabecular thickness, bone mineralization, and mechanical strength in a dose-dependent manner. The result of RT-PCR analysis revealed that naringin down-regulated the mRNA expression levels of BCL-2 and up-regulated BAX, caspase-3 and cytochrome C. In addition, naringin significantly reduced the bone resorption area in vitro. These findings suggest that naringin promotes the apoptosis of osteoclasts by regulating the activity of the mitochondrial apoptosis pathway and prevents OVX-induced osteoporosis in rats.

Naringin prevents ovariectomy-induced osteoporosis and promotes osteoclasts apoptosis through the mitochondria-mediated apoptosis pathway

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Li, Fengbo; Sun, Xiaolei; Ma, Jianxiong; Ma, Xinlong; Zhao, Bin; Zhang, Yang; Tian, Peng; Li, Yanjun; Han, Zhe

2014-01-01

Highlights: • Naringin possesses many pharmacological activities, promotes the proliferation of osteoblast. • Undecalcified histological obtain dynamic parameters of callus formation and remodeling. • Naringin regulate osteoclast apoptosis by mitochondrial pathway. - Abstract: Naringin, the primary active compound of the traditional Chinese medicine Rhizoma drynariae, possesses many pharmacological activities. The present study is an effort to explore the anti-osteoporosis potential of naringin in vivo and in vitro. In vivo, we used ovariectomized rats to clarify the mechanisms by which naringin anti-osteoporosis. In vitro, we used osteoclasts to investigate naringin promotes osteoclasts apoptosis. Naringin was effective at enhancing BMD, trabecular thickness, bone mineralization, and mechanical strength in a dose-dependent manner. The result of RT-PCR analysis revealed that naringin down-regulated the mRNA expression levels of BCL-2 and up-regulated BAX, caspase-3 and cytochrome C. In addition, naringin significantly reduced the bone resorption area in vitro. These findings suggest that naringin promotes the apoptosis of osteoclasts by regulating the activity of the mitochondrial apoptosis pathway and prevents OVX-induced osteoporosis in rats

Protective effects of hesperidin against oxidative stress of tert-butyl hydroperoxide in human hepatocytes.

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Chen, Mingcang; Gu, Honggang; Ye, Yiyi; Lin, Bing; Sun, Lijuan; Deng, Weiping; Zhang, Jingzhe; Liu, Jianwen

2010-10-01

Increasing evidence regarding free radical generating agents and the inflammatory process suggest that accumulation of reactive oxygen species (ROS) could involve hepatotoxicity. Hesperidin, a naturally occurring flavonoid presents in fruits and vegetables, has been reported to exert a wide range of pharmacological effects that include antioxidant, anti-inflammatory, antihypercholesterolemic, and anticarcinogenic actions. However, the cytoprotection and mechanism of hesperidin to neutralize oxidative stress in human hepatic L02 cells remain unclear. In this work, we assessed the capability of hesperidin to prevent tert-butyl hydroperoxide (t-BuOOH)-induced cell damage by augmenting cellular antioxidant defense. Hesperidin significantly protected hepatocytes against t-BuOOH-induced cell cytotoxicity, such as mitochondrial membrane potential (MMP) deplete and lactate dehydrogenase (LDH) release. Hesperidin also remarkably prevented indicators of oxidative stress, such as the ROS and lipid peroxidation level in a dose-dependent manner. Western blot showed that hesperidin facilitated ERK/MAPK phosphorylation which appeared to be responsible for nuclear translocation of Nrf2, thereby inducing cytoprotective heme oxygenase-1 (HO-1) expression. Based on the results described above, it suggested that hesperidin has potential as a therapeutic agent in the treatment of oxidative stress-related hepatocytes injury and liver dysfunctions. Copyright © 2010 Elsevier Ltd. All rights reserved.

The mechanism of Naringin-enhanced remyelination after spinal cord injury

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Wei Rong

2017-01-01

Full Text Available Our previous study revealed that intragastric administration of naringin improved remyelination in rats with spinal cord injury and promoted the recovery of neurological function of the injured spinal cord. This study sought to reveal the mechanisms by which naringin improves oligodendrocyte precursor cell differentiation and maturation, and promotes remyelination. Spinal cord injury was induced in rats by the weight-drop method. Naringin was intragastrically administered daily (20, 40 mg/kg for 4 weeks after spinal cord injury induction. Behavioral assessment, histopathological staining, immunofluorescence spectroscopy, ultrastructural analysis and biochemical assays were employed. Naringin treatment remarkably mitigated demyelination in the white matter, increased the quality of myelinated nerve fibers and myelin sheath thickness, promoted oligodendrocyte precursor cell differentiation by upregulating the expression of NKx2.2 and 2′3′-cyclic nucleotide 3′-phosphodiesterase, and inhibited β-catenin expression and glycogen synthase kinase-3β (GSK-3β phosphorylation. These findings indicate that naringin treatment regulates oligodendrocyte precursor cell differentiation and promotes remyelination after spinal cord injury through the β-catenin/GSK-3β signaling pathway.

Naringin, a natural dietary compound, prevents intestinal tumorigenesis in Apc (Min/+) mouse model.

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Zhang, Yu-Sheng; Li, Ye; Wang, Yan; Sun, Shi-Yue; Jiang, Tao; Li, Cong; Cui, Shu-Xiang; Qu, Xian-Jun

2016-05-01

Naringin is a natural dietary flavonoid compound. We aimed to evaluate the effects of naringin on intestinal tumorigenesis in the adenomatous polyposis coli multiple intestinal neoplasia (Apc (Min/+)) mouse model. Apc (Min/+) mice were given either naringin (150 mg/kg) or vehicle by p.o. gavage daily for 12 consecutive weeks. Mice were killed with ether, and blood samples were collected to assess the concentrations of IL-6 and PGE2. Total intestines were removed, and the number of polyps was examined. Tissue samples of intestinal polyps were subjected to the assays of histopathology, immunohistochemical analysis and Western blotting analysis. Apc (Min/+) mice fed with naringin developed less and smaller polyps in total intestines. Naringin prevented intestinal tumorigenesis without adverse effects. Histopathologic analysis revealed the reduction of dysplastic cells and dysplasia in the adenomatous polyps. The treatments' effects might arise from its anti-proliferation, induction of apoptosis and modulation of GSK-3β and APC/β-catenin signaling pathways. Naringin also exerted its effects on tumorigenesis through anti-chronic inflammation. Naringin prevented intestinal tumorigenesis likely through a collection of activities including anti-proliferation, induction of apoptosis, modulation of GSK-3β and APC/β-catenin pathways and anti-inflammation. Naringin is a potential chemopreventive agent for reducing the risk of colonic cancers.

Biochemical characterization of Aspergillus oryzae recombinant α-l-rhamnosidase expressed in Pichia pastoris.

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Ishikawa, Mai; Shiono, Yoshihito; Koseki, Takuya

2017-12-01

An α-l-rhamnosidase-encoding gene from Aspergillus oryzae, which belongs to the glycoside hydrolase family 78, was cloned and expressed in Pichia pastoris. SDS-PAGE of the purified recombinant α-l-rhamnosidase protein revealed smeared bands with apparent molecular mass of 90-130 kDa. After N-deglycosylation, the recombinant enzyme showed a molecular mass of 70 kDa. The enzyme exhibited optimal activity at a pH of 5.0 and a temperature of 70 °C. Specific activity of the enzyme was higher toward hesperidin than toward naringin, which consist of α-1,6 and α-1,2 linkages, respectively. The activity was also higher toward hesperidin than toward rutin, which consist of 7-O- and 3-O-glycosyl linkages of flavonoids, respectively. Kinetic analysis of the enzyme showed that the Michaelis constant (K m ) was lowest toward rutin, moderate toward naringin, and higher toward p-nitrophenyl-α-l-rhamnopyranoside and hesperidin. Its high catalytic efficiency (k cat /K m ) toward rutin was results of its low K m value while its high catalytic efficiency toward hesperidin was results of a considerably high k cat value. Copyright © 2017 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

Hesperidin, A Popular Antioxidant Inhibits Melanogenesis via Erk1/2 Mediated MITF Degradation

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Heun Joo Lee

2015-08-01

Full Text Available Regulation of melanogenesis has been the focus of treatment for hyperpigmentary skin disorders. Although hesperidin is one of the most well-known, naturally occurring flavonoids with antioxidant and anti-inflammatory effect, its anti-melanogenic effect is not known. The present study aims to determine the anti-melanogenic effect of hespiridin as well as its underlying molecular mechanisms. Melanin contents were measured in normal human melanocytes and B16F10 melanoma cells. Protein and mRNA levels of tyrosinase, microphthalmia-associated transcription factor (MITF, tyrosinase related protein-1 (TRP-1 and TRP-2 were determined. Melanogenesis-regulating signals were examined. In results, hesperidin strongly inhibited melanin synthesis and tyrosinase activity. Hesperidin decreased tyrosinase, TRP-1, and TRP-2 protein expression but increased phospho-extracellular signal-regulated kinase 1/2 (p-Erk1/2 expression. Specific inhibitor of Erk1/2 or proteasome inhibitor reversed the inhibition of melanogenesis induced by hesperidin. Taken together, hesperidin, a popular antioxidant, stimulated Erk1/2 phosphorylation which subsequently degraded MITF which resulted in suppression of melanogenic enzymes and melanin synthesis.

Structural characterization of inclusion complex of hesperidin methyl chalcone and hydroxypropyl-beta-cyclodextrin

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Li, Y.; Li, F.; Chen, X.; Shen, W.

2016-01-01

Hesperidin methyl chalcone (HMC) was a semisynthetic derivative of hesperidin, which owned antiviral and antimicrobial activities. Owing these properties, it can be applied in pharmaceutical industry. However low stability had become a barrier to its application. In order to overcome this problem, an inclusion complex of hesperidin methyl chalcone and hydroxypropyl-beta-cyclodextrin (HP-beta-CD) were prepared by freeze-drying, using some analytical techniques to characterize the inclusion complex, including ultraviolet-visible spectroscopy (UV), Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), X-ray diffractometry (XRD) and differential scanning calorimetry (DSC). The results of these analytical techniques indicated that the hesperidin methyl chalcone has been dispersed completely in the HP-beta-CD without a new compound formed, but entrapped inside the cavity of HP-beta-CD. (author)

Phenolic compounds apigenin, hesperidin and kaempferol reduce in vitro lipid accumulation in human adipocytes.

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Gómez-Zorita, Saioa; Lasa, Arrate; Abendaño, Naiara; Fernández-Quintela, Alfredo; Mosqueda-Solís, Andrea; Garcia-Sobreviela, Maria Pilar; Arbonés-Mainar, Jose M; Portillo, Maria P

2017-11-21

Adipocytes derived from human mesenchymal stem cells (MSCs) are widely used to investigate adipogenesis. Taking into account both the novelty of these MSCs and the scarcity of studies focused on the effects of phenolic compounds, the aim of the present study was to analyze the effect of apigenin, hesperidin and kaempferol on pre-adipocyte and mature adipocytes derived from this type of cells. In addition, the expression of genes involved in TG accumulation was also measured. Pre-adipocytes were cultured from day 0 to day 8 and mature adipocytes for 48 h with the polyphenols at doses of 1, 10 and 25 µM. Apigenin did not show an anti-adipogenic action. Pre-adipocytes treated with hesperidin and kaempferol showed reduced TG content at the three experimental doses. Apigenin did not modify the expression of the main adipogenic genes (c/ebpβ, c/ebpα, pparγ and srebp1c), hesperidin inhibited genes involved in the three phases of adipogenesis (c/ebpβ, srebp1c and perilipin) and kaempferol reduced c/ebpβ. In mature adipocytes, the three polyphenols reduced TG accumulation at the dose of 25 µM, but not at lower doses. All compounds increased mRNA levels of atgl. Apigenin and hesperidin decreased fasn expression. The present study shows the anti-adipogenic effect and delipidating effects of apigenin, hesperidin and kaempferol in human adipocytes derived from hMSCs. While hesperidin blocks all the stages of adipogenesis, kaempferol only inhibits the early stage. Regarding mature adipocytes, the three compounds reduce TG accumulation by activating, at least in part, lipolysis, and in the case of hesperidin and apigenin, also by reducing lipogenesis. The present study shows for the first time the anti-adipogenic effect and delipidating effect of apigenin, hesperidin and kaempferol in human adipocytes derived from MSCs for the first time.

Naringenin Inhibits Adipogenesis and Reduces Insulin Sensitivity and Adiponectin Expression in Adipocytes

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Allison J. Richard

2013-01-01

Full Text Available Adipose tissue development and function are widely studied to examine the relationship between obesity and the metabolic syndrome. It is well documented that the inability of adipose tissue to properly increase its lipid storage capacity during the obese state can lead to metabolic dysfunction. In a blind screen of 425 botanicals, we identified naringenin as an inhibitor of adipocyte differentiation. Naringenin is one of the most abundant citrus flavonoids, and recent studies have demonstrated antihyperlipidemic capabilities. These studies have largely focused on the effects of naringenin on the liver. Our biochemical studies clearly demonstrate that naringenin inhibits adipogenesis and impairs mature fat cell function. Naringenin specifically inhibited adipogenesis in a dose-dependent fashion as judged by examining lipid accumulation and induction of adipocyte marker protein expression. In mature 3T3-L1 adipocytes, naringenin reduced the ability of insulin to induce IRS-1 tyrosine phosphorylation and substantially inhibited insulin-stimulated glucose uptake in a dose-dependent manner and over a time frame of 1.5 to 24 hours. Exposure to naringenin also inhibited adiponectin protein expression in mature murine and human adipocytes. Our studies have revealed that naringenin may have a negative impact on adipocyte-related diseases by limiting differentiation of preadipocytes, by significantly inducing insulin resistance, and by decreasing adiponectin expression in mature fat cells.

Hesperidin as a preventive resistance agent in MCF–7 breast cancer cells line resistance to doxorubicin

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Rifki Febriansah

2014-03-01

Conclusions: Hesperidin has cytotoxic effect on MCF-7/Dox cells with IC50 of 11 μmol/L. Hesperidin did not increased the apoptotic induction combined with doxorubicin. Co-chemotherapy application of doxorubicin and hesperidin on MCF-7/Dox cells showed synergism effect through inhibition of Pgp expression.

Naringenin is a novel inhibitor of Dictyostelium cell proliferation and cell migration

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Russ, Misty; Martinez, Raquel; Ali, Hind; Steimle, Paul A.

2006-01-01

Naringenin is a flavanone compound that alters critical cellular processes such as cell multiplication, glucose uptake, and mitochondrial activity. In this study, we used the social amoeba, Dictyostelium discoideum, as a model system for examining the cellular processes and signaling pathways affected by naringenin. We found that naringenin inhibited Dictyostelium cell division in a dose-dependent manner (IC 5 ∼ 20 μM). Assays of Dictyostelium chemotaxis and multicellular development revealed that naringenin possesses a previously unrecognized ability to suppress amoeboid cell motility. We also found that naringenin, which is known to inhibit phosphatidylinositol 3-kinase activity, had no apparent effect on phosphatidylinositol 3,4,5-trisphosphate synthesis in live Dictyostelium cells; suggesting that this compound suppresses cell growth and migration via alternative signaling pathways. In another context, the discoveries described here highlight the value of using the Dictyostelium model system for identifying and characterizing the mechanisms by which naringenin, and related compounds, exert their effects on eukaryotic cells

The Citrus Flavanone Naringenin Protects Myocardial Cells against Age-Associated Damage

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Eleonora Da Pozzo

2017-01-01

Full Text Available In recent years, the health-promoting effects of the citrus flavanone naringenin have been examined. The results have provided evidence for the modulation of some key mechanisms involved in cellular damage by this compound. In particular, naringenin has been revealed to have protective properties such as an antioxidant effect in cardiometabolic disorders. Very recently, beneficial effects of naringenin have been demonstrated in old rats. Because aging has been demonstrated to be directly related to the occurrence of cardiac disorders, in the present study, the ability of naringenin to prevent cardiac cell senescence was investigated. For this purpose, a cellular model of senescent myocardial cells was set up and evaluated using colorimetric, fluorimetric, and immunometric techniques. Relevant cellular senescence markers, such as X-gal staining, cell cycle regulator levels, and the percentage of cell cycle-arrested cells, were found to be reduced in the presence of naringenin. In addition, cardiac markers of aging-induced damage, including radical oxidative species levels, mitochondrial metabolic activity, mitochondrial calcium buffer capacity, and estrogenic signaling functions, were also modulated by the compound. These results suggested that naringenin has antiaging effects on myocardial cells.

Solvatochromism of naringenin in aqueous alcoholic mixtures

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Faraji Mohammad

2016-01-01

Full Text Available The spectral change of naringenin was studied by Uv-vis spectrophotometric method in binary mixtures of water with methanol, ethanol and 1-propanol at 25°C. The effect of solvent was investigated by analysis of electron transition energy at the maximum absorption wavelength as a function of Kamlet and Taft parameters of mixtures by means of linear solvation energy relationships. The nonlinear response of solvatochromism was explained based on solute-solvent and solvent-solvent interactions. The possible preferential solvation of naringenin by each of solvents was studied through a modified preferential solvation model which considers the hydrogen bonding interactions between the prior solvents due to solvent-solvent interactions. The preferential solvation parameters and local mole fraction distribution around the solute were calculated. Results indicate that naringenin prefers to be more solvated by the complex solvating species and organic solvents than water.

Molecular characterization and enzymatic hydrolysis of naringin extracted from kinnow peel waste.

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Puri, Munish; Kaur, Aneet; Schwarz, Wolfgang H; Singh, Satbir; Kennedy, J F

2011-01-01

Kinnow peel, a waste rich in glycosylated phenolic substances, is the principal by-product of the citrus fruit processing industry and its disposal is becoming a major problem. This peel is rich in naringin and may be used for rhamnose production by utilizing α-L-rhamnosidase (EC 3.2.1.40), an enzyme that catalyzes the cleavage of terminal rhamnosyl groups from naringin to yield prunin and rhamnose. In this work, infrared (IR) spectroscopy confirmed molecular characteristics of naringin extracted from kinnow peel waste. Further, recombinant α-L-rhamnosidase purified from Escherichia coli cells using immobilized metal-chelate affinity chromatography (IMAC) was used for naringin hydrolysis. The purified enzyme was inhibited by Hg2+ (1 mM), 4-hydroxymercuribenzoate (0.1 mM) and cyanamide (0.1 mM). The purified enzyme established hydrolysis of naringin extracted from kinnow peel and thus endorses its industrial applicability for producing rhamnose. Copyright © 2010 Elsevier B.V. All rights reserved.

Hesperidin and low dose gamma irradiation alleviate rosiglitazone -induced cardiotoxicity in type 2 diabetic rats

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Morcos, N.Y.; Abdel-Ghaffar, A.B.; Osman, S.A.; Mohamed, M.Kh.; Arbid, M.S.; El-Eraky, W.I.

2012-01-01

Aim: The present study was designed to investigate the cardio protective effect of hesperidin and low dose γ- irradiation (LDR) against rosiglitazone cardiotoxicity. Experiment: Type 2 diabetes mellitus (T2DM) was induced in rats by single intraperitoneal injection of streptozotocin (STZ) followed by nicotinamide (NIC) (65 and 110 mg/kg b.wt, respectively). The diabetic rats were divided into 5 groups: untreated, LDR, LDR+ rosiglitazone, LDR + Hesperidin, LDR+ rosiglitazone + Hesperidin for one month, and blood and tissue samples were collected. Results: The diabetic rats showed elevated serum creatine kinase (CK-MB), lactate dehydrogenase (LDH), C-reactive protein (CRP), hyaluronidase activity, and reduced serum nitric oxide (NO) level, hematocrit % as well as final body weight, and pathological alterations in myocardial tissue. Treatment with LDR + rosiglitazone + Hesperidin ameliorated all these abnormalities approaching control levels. Conclusion: Results indicate the possible cardio protective role of hesperidin and LDR against rosiglitazone cardiotoxicity.

Antioxidant capacity of hesperidin from citrus peel using electron spin resonance and cytotoxic activity against human carcinoma cell lines.

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Al-Ashaal, Hanan A; El-Sheltawy, Shakinaz T

2011-03-01

Hesperidin is a flavonoid that has various pharmacological activities including anti-inflammatory, antimicrobial and antiviral activities. The aim of the study is the isolation of hesperidin from the peel of Citrus sinensis L. (Rutaceae), and the evaluation of its antioxidant capacity and cytotoxicity against different human carcinoma cell lines. In the present work, hesperidin is identified and confirmed using chromatographic and spectral analysis. To correlate between hesperidin concentration and antioxidant capacity of peel extracts, extraction was carried out using 1% HCl-MeOH, MeOH, alkaline solution, the concentration of hesperidin determined qualitatively and quantitatively using high performance thin layer chromatography (HPTLC), high performance liquid chromatography (HPLC) analysis, in vitro antioxidant capacity of hesperidin and the extracts against free radical diphenylpicrylhydrazyl (DPPH•) performed using an electron spin resonance spectrophotometer (ESR). Cytotoxic assay against larynx, cervix, breast and liver carcinoma cell lines was performed. Hesperidin was found to be moderately active as an antioxidant agent; its capacity reached 36%. In addition, the results revealed that hesperidin exhibited pronounced anticancer activity against the selected cell lines. IC₅₀ were 1.67, 3.33, 4.17, 4.58 µg/mL, respectively. Orange peels are considered to be a cheap source for hesperidin which may be used in the pharmaceutical industry as a natural chemopreventive agent. Hesperidin and orange peel extract could possess antioxidant properties with a wide range of therapeutic applications.

Hesperidin produces cardioprotective activity via PPAR-γ pathway in ischemic heart disease model in diabetic rats.

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Yogeeta O Agrawal

Full Text Available The present study investigated the effect of hesperidin, a natural flavonoid, in cardiac ischemia and reperfusion (I/R injury in diabetic rats. Male Wistar rats with diabetes were divided into five groups and were orally administered saline once daily (IR-sham and IR-control, Hesperidin (100 mg/kg/day; IR-Hesperidin, GW9962 (PPAR-γ receptor antagonist, or combination of both for 14 days. On the 15th day, in the IR-control and IR-treatment groups, rats were subjected to left anterior descending (LAD coronary artery occlusion for 45 minutes followed by a one-hour reperfusion. Haemodynamic parameters were recorded and rats were sacrificed; hearts were isolated for biochemical, histopathological, ultrastructural and immunohistochemistry. In the IR-control group, significant ventricular dysfunctions were observed along with enhanced expression of pro-apoptotic protein Bax. A decline in cardiac injury markers lactate dehydrogenase activity, CK-MB and increased content of thiobarbituric acid reactive substances, a marker of lipid peroxidation, and TNF-α were observed. Hesperidin pretreatment significantly improved mean arterial pressure, reduced left ventricular end-diastolic pressure, and improved both inotropic and lusitropic function of the heart (+LVdP/dt and -LVdP/dt as compared to IR-control. Furthermore, hesperidin treatment significantly decreased the level of thiobarbituric acid reactive substances and reversed the activity of lactate dehydrogenase towards normal value. Hesperidin showed anti-apoptotic effects by upregulating Bcl-2 protein and decreasing Bax protein expression. Additionally, histopathological and ultrastructural studies reconfirmed the protective action of hesperidin. On the other hand, GW9662, selective PPAR-γ receptor antagonist, produced opposite effects and attenuated the hesperidin induced improvements. The study for the first time evidence the involvement of PPAR-γ pathway in the cardioprotective activity of

Synthesis of naringin 6"-ricinoleate using immobilized lipase

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Almeida Verônica M

2012-05-01

Full Text Available Abstract Background Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to the flavonoid sugar unit using immobilized lipase. However, there is limited research regarding hydroxylation of unsaturated fatty acids as an answer to the low solubility challenge. In this work, we describe the reaction of naringin with castor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica. Analysis of the 1H and 13 C NMR (1D and 2D spectra and literature comparison were used to characterise the obtained acyl derivative. Results After allowing the reaction to continue for 120 hours (in acetone media, 50°C, the major product obtained was naringin 6″-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6″-ricinoleate was determined using NMR analysis, including bidimensional (2D experiments. Conclusion Using immobilized lipase from C. antarctica, the best conversion reaction was observed using castor oil containing ricinoleic acid as the acylating agent rather than an isolated fatty acid. Graphical abstract

Flavonoid Naringenin: A Potential Immunomodulator for Chlamydia trachomatis Inflammation

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Abebayehu N. Yilma

2013-01-01

Full Text Available Chlamydia trachomatis, the agent of bacterial sexually transmitted infections, can manifest itself as either acute cervicitis, pelvic inflammatory disease, or a chronic asymptomatic infection. Inflammation induced by C. trachomatis contributes greatly to the pathogenesis of disease. Here we evaluated the anti-inflammatory capacity of naringenin, a polyphenolic compound, to modulate inflammatory mediators produced by mouse J774 macrophages infected with live C. trachomatis. Infected macrophages produced a broad spectrum of inflammatory cytokines (GM-CSF, TNF, IL-1β, IL-1α, IL-6, IL-12p70, and IL-10 and chemokines (CCL4, CCL5, CXCL1, CXCL5, and CXCL10 which were downregulated by naringenin in a dose-dependent manner. Enhanced protein and mRNA gene transcript expressions of TLR2 and TLR4 in addition to the CD86 costimulatory molecule on infected macrophages were modulated by naringenin. Pathway-specific inhibition studies disclosed that p38 mitogen-activated-protein kinase (MAPK is involved in the production of inflammatory mediators by infected macrophages. Notably, naringenin inhibited the ability of C. trachomatis to phosphorylate p38 in macrophages, suggesting a potential mechanism of its attenuation of concomitantly produced inflammatory mediators. Our data demonstrates that naringenin is an immunomodulator of inflammation triggered by C. trachomatis, which possibly may be mediated upstream by modulation of TLR2, TLR4, and CD86 receptors on infected macrophages and downstream via the p38 MAPK pathway.

Preparation and Characterization of Naringenin-Loaded Elastic Liposomes for Topical Application.

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Ming-Jun Tsai

Full Text Available Excessive production of radical oxygen species in skin is a contributor to a variety of skin pathologies. Naringenin is a potent antioxidant. The purpose of the present study was to develop elastic liposomes for naringenin topical application. Naringenin-loaded elastic liposomes containing different amounts of Tween 80 and cholesterol were prepared. The physicochemical properties including vesicle size, surface charge, encapsulation efficiency, and permeability capacity were determined to evaluate the effect of components. The stability of formulation and skin irritation caused by drug-loaded elastic liposomes were also evaluated for assessment of the clinical utility of elastic liposomes. Saturated aqueous solution of naringenin and naringenin dissolved in 10% Tween 80 solution (5 mg/mL were used as the control group. The result showed that in using elastic liposomes as carrier, the deposition amounts in the skin of naringenin were significantly increased about 7.3~11.8-fold and 1.2~1.9-fold respectively, when compared with the saturated aqueous solution and Tween 80 solution-treated groups. The level of drug was more than 98.89±3.90% after 3 months of storage at 4℃. In a skin irritation test, the result showed experimental formulation exhibit considerably less irritating than the positive control (paraformaldehyde-treated group, suggesting its potential therapeutic application.

Sonochemical effects on 14 flavonoids common in citrus: relation to stability.

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Liping Qiao

Full Text Available The sonochemical effects of ultrasound (US treatment on 14 flavonoids representing the main flavonoids in citrus fruit were investigated in a standard mixture by stability evaluation of a model system. Degradation products were further tentatively identified by Fourier transform infrared spectroscopy and high-performance liquid chromatography-ultraviolet detection-electrospray ionization tandem mass spectrometry. Thirteen flavonoids (i.e., eriocitrin, narirutin, neohesperidin, quercitrin, eridictyol, didymin, naringenin, luteolin, sinensetin, nobiletin, tangeretin, naringin, and hesperidin were fairly stable whereas quercetin was degraded significantly by US treatment. The types of solvent and temperature used were important factors that determined the resulting degradation reactions. The degradation rate of quercetin was highest in 80% ethanol aqueous solution and decreased with increasing temperature. Longer US durations caused increases in the extent of quercetin degradation. Liquid height, ultrasonic intensity, pulse length, and duty cycle of US affected degradation rates but did not change the nature of degradation of the flavonoids. Four types of reactions occurred simultaneously for quercetin under US treatment: oxidation, addition, polymerization, and decomposition. Eight degradation products were tentatively identified as dimer, alcohol addition, oxidation, and decomposition products.

Enhancement of Naringenin Biosynthesis from Tyrosine by Metabolic Engineering of Saccharomyces cerevisiae.

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Lyu, Xiaomei; Ng, Kuan Rei; Lee, Jie Lin; Mark, Rita; Chen, Wei Ning

2017-08-09

Flavonoids are an important class of plant polyphenols that possess a variety of health benefits. In this work, S. cerevisiae was metabolically engineered to produce the flavonoid naringenin, using tyrosine as the precursor. Our strategy to improve naringenin production comprised three modules. In module 1, we employed a modified GAL system to overexpress the genes of the naringenin biosynthesis pathway and investigated their synergistic action. In module 2, we simultaneously up-regulated acetyl-CoA production and down-regulated fatty acid biosynthesis in order to increase the precursor supply, malonyl-CoA. In module 3, we engineered the tyrosine biosynthetic pathway to eliminate the feedback inhibition of tyrosine and also down-regulated competing pathways. It was found that modules 1 and 3 played important roles in improving naringenin production. We succeeded in producing up to ∼90 mg/L of naringenin in our final strain, which is a 20-fold increase as compared to the parental strain.

Cellular mechanisms underlying the laxative effect of flavonol naringenin on rat constipation model.

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Zi-Huan Yang

Full Text Available BACKGROUND & AIMS: Symptoms of constipation are extremely common, especially in the elderly. The present study aim to identify an efficacious treatment strategy for constipation by evaluating the secretion-promoting and laxative effect of a herbal compound, naringenin, on intestinal epithelial anion secretion and a rat constipation model, respectively. METHODS/PRINCIPAL FINDINGS: In isolated rat colonic crypts, mucosal addition of naringenin (100 microM elicited a concentration-dependent and sustained increase in the short-circuit current (I(SC, which could be inhibited in Cl- free solution or by bumetanide and DPC (diphenylamine-2-carboxylic acid, but not by DIDS (4, 4'- diisothiocyanatostilbene-2, 2'-disulfonic acid. Naringenin could increase intracellular cAMP content and PKA activity, consisted with that MDL-12330A (N-(Cis-2-phenyl-cyclopentyl azacyclotridecan-2-imine-hydrochloride pretreatment reduced the naringenin-induced I(SC. In addition, significant inhibition of the naringenin-induced I(SC by quinidine indicated that basolateral K+ channels were involved in maintaining this cAMP-dependent Cl- secretion. Naringenin-evoked whole cell current which exhibited a linear I-V relationship and time-and voltage- independent characteristics was inhibited by DPC, indicating that the cAMP activated Cl- conductance most likely CFTR (cystic fibrosis transmembrane conductance regulator was involved. In rat constipation model, administration of naringenin restored the level of fecal output, water content and mucus secretion compared to loperamide-administrated group. CONCLUSIONS: Taken together, our data suggest that naringenin could stimulate Cl- secretion in colonic epithelium via a signaling pathway involving cAMP and PKA, hence provide an osmotic force for subsequent colonic fluid secretion by which the laxative effect observed in the rat constipation model. Naringenin appears to be a novel alternative treatment strategy for constipation.

Gum tragacanth stabilized green gold nanoparticles as cargos for Naringin loading: A morphological investigation through AFM.

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Rao, Komal; Imran, Muhammad; Jabri, Tooba; Ali, Imdad; Perveen, Samina; Shafiullah; Ahmed, Shakil; Shah, Muhammad Raza

2017-10-15

Gold nanoparticles (AuNPs) have attracted greater scientific interests for the construction of drugs loading cargos due to their biocompatibility, safety and facile surface modifications. This study deals with the fabrication of gum tragacanth (GT) green AuNPs as carrier for Naringin, a less water soluble therapeutic molecule. The optimized AuNPs were characterized through UV-vis spectroscopy, FT-IR and atomic force microscope (AFM). Naringin loaded nanoparticles were investigated for their bactericidal potentials using Tetrazolium Microplate assay. Morphological studies conducted via AFM revealed spherical shape for AuNPs with nano-range size and stabilized by GT multi-functional groups. The AuNPs acted as carrier for increased amount of Naringin. Upon loading in AuNPs, Naringin An increased in the bactericidal potentials of Naringin was observed after loading on AuNPs against various tested bacterial strains. This was further authenticated by the surface morphological analysis, showing enhanced membrane destabilizing effects of loaded Naringin. The results suggest that GT stabilized green AuNPs can act as effective delivery vehicles for enhancing bactericidal potentials of Naringin. Copyright © 2017 Elsevier Ltd. All rights reserved.

Influence of hesperidin and vitamin C on glycemic parameters, lipid profile, and DNA damage in rats treated with sucrose overload

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SILVIA I.R. FRANKE

2018-04-01

Full Text Available ABSTRACT We evaluated the influence of hesperidin and vitamin C (VitC on glycemic parameters, lipid profile, and DNA damage in male Wistar rats treated with sucrose overload. Rats were divided into six experimental groups: I-water control; II-sucrose control; III-hesperidin control; IV-VitC control; V-co-treatment of sucrose plus hesperidin; VI-co-treatment of sucrose plus VitC. We measured the levels of triglycerides, total cholesterol, HDL-c, LDL-c, fasting glucose, and glycated hemoglobin (A1C. DNA damage was evaluated in blood and brain cells using the comet assay and the micronucleus test was used to evaluate chromosomal damages in the rat bone marrow. Co-treatment with VitC, but not with hesperidin, normalized the serum glucose. No effect of co-treatments was observed on A1C. The co-treatment with VitC or hesperidin did not influence the lipid profile (p>0.05. Rats co-treated with hesperidin had a significantly lower DNA damage level in blood (p0.05. Hesperidin and VitC showed different effects on sucrose and DNA damage levels. While VitC lowered the serum glucose, hesperidin reduced the DNA damage.

Effect of 4G-alpha-glucopyranosyl hesperidin on brown fat adipose tissue- and cutaneous-sympathetic nerve activity and peripheral body temperature.

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Shen, Jiao; Nakamura, Hiroyasu; Fujisaki, Yoshiyuki; Tanida, Mamoru; Horii, Yuko; Fuyuki, Risa; Takumi, Hiroko; Shiraishi, Koso; Kometani, Takashi; Nagai, Katsuya

2009-09-11

Changes in the activity of the autonomic nervous system are good indicators of alterations in physiological phenomena such as the body temperature, blood glucose, blood pressure. Hesperidin, a flavanone known as vitamin P, has been shown to reduce the levels of serum lipids, cholesterol, and blood pressure. However, hesperidin is not water-soluble and is not well absorbed from the intestine. G-hesperidin (4G-alpha-glucopyranosyl hesperidin) is more water-soluble and more rapidly absorbed than hesperidin. In order to clarify the functions of G-hesperidin, we examined the effects of oral administration of G-hesperidin on interscapular brown adipose tissue-sympathetic nerve activity (BAT-SNA) and cutaneous sympathetic nerve activity (CASNA) in rats weighing about 300 g. In this study, we found that oral administration of 60 mg of G-hesperidin increased the BAT-SNA but decreased the CASNA in urethane-anesthetized rats. Since an elevation in BAT-SNA increases heat production (i.e. body temperature (BT)) and a decrease in CASNA increases cutaneous perfusion, we examined whether oral administration of G-hesperidin had an effect on the peripheral BT in rats. Consequently, we observed that the subcutaneous BT at the caudal end of the back after oral administration of 60 mg of G-hesperidin was significantly higher than the subcutaneous BT after oral administration of water in conscious rats. These findings suggest that G-hesperidin enhances the BAT-SNA and suppresses the CASNA resulting in an increase in the peripheral BT, probably by an increase in the thermogenesis in the BAT and an elevation in the cutaneous blood flow.

Negative regulation of β-catenin/Tcf signaling by naringenin in AGS gastric cancer cell

International Nuclear Information System (INIS)

Lee, Ju Hyung; Park, Chi Hoon; Jung, Kyung Chae; Rhee, Ho Sung; Yang, Chul Hak

2005-01-01

Functional activation of β-catenin/Tcf signaling plays an important role in early events in carcinogenesis. We examined the effect of naringenin against β-catenin/Tcf signaling in gastric cancer cells. Reporter gene assay showed that naringenin inhibited β-catenin/Tcf signaling efficiently. In addition, the inhibition of β-catenin/Tcf signaling by naringenin in HEK293 cells transiently transfected with constitutively mutant β-catenin gene, whose product is not phosphorylated by GSK3β, indicates that its inhibitory mechanism was related to β-catenin itself or downstream components. To investigate the precise inhibitory mechanism, we performed immunofluorescence, Western blot, and EMSA. As a result, our data revealed that the β-catenin distribution and the levels of nuclear β-catenin and Tcf-4 proteins were unchanged after naringenin treatment. Moreover, the binding activities of Tcf complexes to consensus DNA were not affected by naringenin. Taken together, these data suggest that naringenin inhibits β-catenin/Tcf signaling in gastric cancer with unknown mechanisms

Hesperidin inhibits HeLa cell proliferation through apoptosis mediated by endoplasmic reticulum stress pathways and cell cycle arrest

International Nuclear Information System (INIS)

Wang, Yaoxian; Yu, Hui; Zhang, Jin; Gao, Jing; Ge, Xin; Lou, Ge

2015-01-01

Hesperidin (30, 5, 9-dihydroxy-40-methoxy-7-orutinosyl flavanone) is a flavanone that is found mainly in citrus fruits and has been shown to have some anti-neoplastic effects. The aim of the present study was to investigate the effect of hesperidin on apoptosis in human cervical cancer HeLa cells and to identify the mechanism involved. Cells were treated with hesperidin (0, 20, 40, 60, 80, and 100 μM) for 24, 48, or 72 h and relative cell viability was assessed using the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. Hesperidin inhibited the proliferation of HeLa cells in a concentration- and time-dependent manner. Hesperidin-induced apoptosis in HeLa cells was characterized by increased nuclear condensation and DNA fragmentation. Furthermore, increased levels of GADD153/CHOP and GRP78 indicated hesperidin-induced apoptosis in HeLa cells involved a caspase-dependent pathway, presumably downstream of the endoplasmic reticulum stress pathway. Both of these proteins are hallmarks of endoplasmic reticulum stress. Hesperidin also promoted the formation of reactive oxygen species, mobilization of intracellular Ca 2+ , loss of mitochondrial membrane potential (ΔΨm), increased release of cytochrome c and apoptosis-inducing factor from mitochondria, and promoted capase-3 activation. It also arrested HeLa cells in the G0/G1 phase in the cell cycle by downregulating the expression of cyclinD1, cyclinE1, and cyclin-dependent kinase 2 at the protein level. The effect of hesperidin was also verified on the human colon cancer cell HT-29 cells. We concluded that hesperidin inhibited HeLa cell proliferation through apoptosis involving endoplasmic reticulum stress pathways and cell cycle arrest

Flavonoid, hesperidine, total phenolic contents and antioxidant ...

African Journals Online (AJOL)

Additionally, the antioxidant activities were also determined by ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity. C. hystrix had the highest flavonoid and total phenolic contents while C. aurantifolia had the highest hesperidine content. The antioxidant activity of ...

Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans

DEFF Research Database (Denmark)

Nielsen, Inge Lise F; Chee, Winnie S S; Poulsen, Lea

2006-01-01

Hesperidin is the predominant polyphenol consumed from citrus fruits and juices. However, hesperidin is proposed to have limited bioavailability due to the rutinoside moiety attached to the flavonoid. The aim of this study was to demonstrate in human subjects that the removal of the rhamnose group...... to yield the corresponding flavonoid glucoside (i.e., hesperetin-7-glucoside) will improve the bioavailability of the aglycone hesperetin. Healthy volunteers (n=16) completed the double-blind, randomized, crossover study. Subjects randomly consumed hesperetin equivalents supplied as orange juice...... that the bioavailability of hesperidin was modulated by enzymatic conversion to hesperetin-7-glucoside, thus changing the absorption site from the colon to the small intestine. This may affect future interventions concerning the health benefits of citrus flavonoids....

The effect of ozone and naringin on intestinal ischemia/reperfusion injury in an experimental model.

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Isik, Arda; Peker, Kemal; Gursul, Cebrail; Sayar, Ilyas; Firat, Deniz; Yilmaz, Ismayil; Demiryilmaz, Ismail

2015-09-01

The aim of the study was to evaulate the effect of ozone and naringin on the intestine after intestinal ischemia-reperfusion(II/R) injury. Thirty five rats divided into 5 groups of 7 animals: control, II/R, ozone, naringin and naringin + ozone. Only laparotomy and exploration of the superior mesenteric artery (SMA) were done in control group. In the experimental groups, SAM was occluded for 1 h and reperfused for 1 h. 15 min after ischemia, ozone (25 μg/ml, 0.5 mg/kg), naringin (80 mg/kg) and naringin + ozone(80 mg/kg + 25 μg/ml, 0.5 mg/kg) were infused intraperitoneally to each groups. Ileum tissues were harvested to determine intestinal mucosal injury and oxidative stress markers. For SMA occlusion, different than literature, silk suture binding was used. Oxidative stress markers were significantly low in experimental groups compared with II/R group (p < 0.05). Histopathologically, the injury score was significantly low at experimental groups compared with II/R group (p < 0.05). The lowest injury score was encountered at naringine + ozone group. Ozone alone or combined with naringin has a protective effect for mesenteric ischemia. Instead of using instruments such as clamps in the II/R rat model, silk binding may be used safely. Copyright © 2015 IJS Publishing Group Limited. Published by Elsevier Ltd. All rights reserved.

NARINGENIN ENHANCED EFFICIENCY OF GUS ACTIVITY IN Passiflora mollissima (H.B.K. Bailey

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G.O. Cancino

2004-06-01

Full Text Available The flavonoid naringenin has been investigated as a possible vir gene inducer in Agrobacterium-mediated transformation in Passiflora mollissima, P. giberti and Nicotiana tabacum cv. Xanthi. The transformation efficiency percentage of explants showing blue GUS expression and the extent of staining following inoculation with Agrobacterium tumefaciens strains EHA 105 and 1065, carrying gus and nptII genes was enhanced with the supplementation of the co-cultivation medium with naringenin. Supplementation of medium with 100µM (strain EHA 105 and 300 µM (strain 1065 naringenin was most effective at enhancing mean (±s.e.m., n=3 GUS activity in leaf explants (20.3 ± 2.4%, strain EHA; 105; 6.0 ± 0.57%, strain 1065 and nodal segments (16.7 ± 2.4% strain EHA 105; 8.3 ± 0.57% strain 1065 of P. mollissima. In P. giberti and N. tabacum maximum GUS activity was obtained in leaf and root explants with 100µM naringenin for both strains analysed. Additionally, when naringenin was added to Luria Bertani (LB medium, both bacterial growth via optical density and colony forming units were higher when compared to control. This is the first report of the use of naringenin to enhance gene transfer from Agrobacterium to plants. These findings suggest that naringenin can be used as an alternative to acetosyringone for vir gene induction in Agrobacterium. This approach may be especially useful in plants that are generally recalcitrant to Agrobacterium-mediatedtransformation.

Effects of naringin on apoptosis and oxidative stress in type 2 diabetic rats

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Adelani, Isaacson; Bankole, Esther; Rotimi, Oluwakemi; Rotimi, Solomon

2018-04-01

Oxidative stress and apoptosis have been reported to play major roles in the pathogenesis of Type 2 Diabetes Mellitus (T2DM) through insulin resistance and β-cell dysfunction. Naringin is a citrus derived flavonoid that has been reported for its antioxidant properties. Even though effects of naringin in T2DM related oxidative stress has been reported, varying dose concentration in oxidative stress and mechanism of action involving T2DM related apoptosis is far-fetched. This research studied the effects of naringin at varying dose concentration on apoptosis, biomarkers of organ function and oxidative stress in high fat diet/low-streptozotocin-induced T2DM in albino Wistar rats. Diabetic rats were treated with naringin at 50mg/kg, 100mg/kg and 200mg/kg body weight for 21 days. Some biomarkers of organ function and oxidative stress in the animals were assayed using spectrophotometric techniques. The levels of expression of caspases and apoptotic regulators were quantified using semi-quantitative reverse transcriptase polymerase chain reaction (RT PCR). Enzyme - linked immunosorbent assay was used to determine inducible nitric oxide synthase (iNOS) level. Naringin treatment shows a dose dependent significant (plipid peroxidation, glutathione- s-transferase, glutathione peroxidase and glutathione reductase activities in the liver. Naringin treatment also showed a significant (p<0.05) increase in the expression of caspase 3 and reduction in BCL-2 as against the diabetic control. In addition, there was dose dependent decrease in plasma CO2 concentration and increase in the plasma iNOS concentration as compared to the diabetic control. This result highlights positive effect of naringin as an antioxidant, its role in apoptosis and also reverting the effects of organ damage in type 2 diabetes.

Structural characterization and bioavailability of ternary nanoparticles consisting of amylose, α-linoleic acid and β-lactoglobulin complexed with naringin.

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Feng, Tao; Wang, Ke; Liu, Fangfang; Ye, Ran; Zhu, Xiao; Zhuang, Haining; Xu, Zhimin

2017-06-01

Naringin is a bioflavonoid that is rich in citrus plants and possesses enormous health benefits. However, the use of naringin as a nutraceutical is significantly limited by its low bioavailability. In this study, a novel water-soluble ternary nanoparticle material consisting of amylose, α-linoleic acid and β-lactoglobulin was developed to encapsulate naringin to improve its bioavailability. The physicochemical characteristics of the ternary nanoparticle-naringin inclusion complex were analysed by ultraviolet-visible spectroscopy (UV), Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), high-resolution transmission electron microscopy (TEM), X-ray diffractometry (XRD) and particle size distribution. The results confirmed the formation of the ternary nanoparticle-naringin inclusion complex. The encapsulation efficiency (EE) and loading content (LC) of the ternary nanoparticle-naringin inclusion complex were 78.73±4.17% and 14.51±3.43%, respectively. In addition, the results of the ternary nanoparticle-naringin inclusion complex in simulated gastric fluid (SGF) and simulated intestinal fluid (SIF) demonstrated that naringin can be gradually released from the complex. In conclusion, ternary nanoparticles are considered promising carriers to effectively improve the bioavailability of naringin. Copyright © 2017 Elsevier B.V. All rights reserved.

Health benefits of orange juice and citrus flavonoids

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The main flavonoids found in orange juice are hesperidin and naringenin, which can affect several metabolic routes that improve blood serum antioxidant capacity and anti-inflammatory performance, while decreasing insulin resistance protecting against diabetes and metabolic syndrome. In addition, or...

Mechanism of Fructus Aurantii Flavonoids Promoting Gastrointestinal Motility: From Organic and Inorganic Endogenous Substances Combination Point of View.

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Wang, Shuai; Bao, Yong-Rui; Li, Tian-Jiao; Yu, Ting; Chang, Xin; Yang, Guan-Lin; Meng, Xian-Sheng

2017-01-01

Fructus Aurantii (FA) derived from the dried, and unripe fruit of Citrus aurantium L. is one of the commonly used traditional Chinese medicines to treat gastrointestinal motility dysfunction diseases. According to the literature research, FA flavonoids (FAF) are important active ingredients of FA promoting gastrointestinal motility, but the exact material basis and mechanism of action are still not very clear. This experiment was designed to illustrate the material basis of FAF promoting gastrointestinal motility and explore the mechanism of action from an organic and inorganic combination point of view. In this experiment, high-performance liquid chromatography (HPLC) method was used to analyze the composition and content of FAF. Based on the prominent prokinetic effect of FAF on mice, the mechanism of action was speculated through a combination of HPLC coupled with quadrupole time-of-flight mass spectrometry (HPLC-QTOF-MS) and inductively coupled plasma mass spectrometry (ICP-MS). With the method of HPLC, ten dominating components of FAF including neoeriocitrin, narirutin, rhoifolin, naringin, hesperidin, neohesperidin, neoponcirin, naringenin, hesperetin, and nobiletin accounting for more than 86% of FAF were identified. Combined HPLC-QTOF-MS with ICP-MS, the endogenous substances with difference in the blood of mice were analyzed, in which 4-dimethylallyltryptophan, corticosterone, phytosphingosine, sphinganine, LysoPC (20:4(5Z, 8Z, 11Z, 14Z)), LysoPC(18:2 (9Z, 12Z)), and Ca 2+ , Mg 2+ , Zn 2+ metal ions had significant changes, involving tryptophan metabolism, corticosterone metabolism, sphingolipid metabolism, and other pathways. The results preliminarily elaborated the mechanism of FAF promoting gastrointestinal motility from an organic and inorganic point of view, which provide valuable information for researching and developing new multi-component Chinese medicine curing gastrointestinal underpower associated diseases. Fructus Aurantii flavonoids are one

Naringin ameliorates gentamicin-induced nephrotoxicity and associated mitochondrial dysfunction, apoptosis and inflammation in rats: Possible mechanism of nephroprotection

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Sahu, Bidya Dhar [Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology (IICT), Hyderabad 500 007 (India); Tatireddy, Srujana [National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad 500 037 (India); Koneru, Meghana [Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology (IICT), Hyderabad 500 007 (India); Borkar, Roshan M. [National Centre for Mass Spectrometry, Indian Institute of Chemical Technology (IICT), Hyderabad 500 007 (India); Kumar, Jerald Mahesh [CSIR-Centre for Cellular and Molecular Biology (CCMB), Hyderabad 500 007 (India); Kuncha, Madhusudana [Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology (IICT), Hyderabad 500 007 (India); Srinivas, R. [National Centre for Mass Spectrometry, Indian Institute of Chemical Technology (IICT), Hyderabad 500 007 (India); Shyam Sunder, R. [Faculty of Pharmacy, Osmania University, Hyderabad 500 007 (India); Sistla, Ramakrishna, E-mail: sistla@iict.res.in [Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology (IICT), Hyderabad 500 007 (India)

2014-05-15

Gentamicin-induced nephrotoxicity has been well documented, although its underlying mechanisms and preventive strategies remain to be investigated. The present study was designed to investigate the protective effect of naringin, a bioflavonoid, on gentamicin-induced nephrotoxicity and to elucidate the potential mechanism. Serum specific renal function parameters (blood urea nitrogen and creatinine) and histopathology of kidney tissues were evaluated to assess the gentamicin-induced nephrotoxicity. Renal oxidative stress (lipid peroxidation, protein carbonylation, enzymatic and non-enzymatic antioxidants), inflammatory (NF-kB [p65], TNF-α, IL-6 and MPO) and apoptotic (caspase 3, caspase 9, Bax, Bcl-2, p53 and DNA fragmentation) markers were also evaluated. Significant decrease in mitochondrial NADH dehydrogenase, succinate dehydrogenase, cytochrome c oxidase and mitochondrial redox activity indicated the gentamicin-induced mitochondrial dysfunction. Naringin (100 mg/kg) treatment along with gentamicin restored the mitochondrial function and increased the renal endogenous antioxidant status. Gentamicin induced increased renal inflammatory cytokines (TNF-α and IL-6), nuclear protein expression of NF-κB (p65) and NF-κB-DNA binding activity and myeloperoxidase (MPO) activity were significantly decreased upon naringin treatment. In addition, naringin treatment significantly decreased the amount of cleaved caspase 3, Bax, and p53 protein expression and increased the Bcl-2 protein expression. Naringin treatment also ameliorated the extent of histologic injury and reduced inflammatory infiltration in renal tubules. U-HPLS-MS data revealed that naringin co-administration along with gentamicin did not alter the renal uptake and/or accumulation of gentamicin in kidney tissues. These findings suggest that naringin treatment attenuates renal dysfunction and structural damage through the reduction of oxidative stress, mitochondrial dysfunction, inflammation and apoptosis in

Naringenin degradation by the endophytic diazotroph Herbaspirillum seropedicae SmR1.

Science.gov (United States)

Marin, A M; Souza, E M; Pedrosa, F O; Souza, L M; Sassaki, G L; Baura, V A; Yates, M G; Wassem, R; Monteiro, R A

2013-01-01

Several bacteria are able to degrade flavonoids either to use them as carbon sources or as a detoxification mechanism. Degradation pathways have been proposed for several bacteria, but the genes responsible are not known. We identified in the genome of the endophyte Herbaspirillum seropedicae SmR1 an operon potentially associated with the degradation of aromatic compounds. We show that this operon is involved in naringenin degradation and that its expression is induced by naringenin and chrysin, two closely related flavonoids. Mutation of fdeA, the first gene of the operon, and fdeR, its transcriptional activator, abolished the ability of H. seropedicae to degrade naringenin.

Urea cycle pathway targeted therapeutic action of naringin against ammonium chloride induced hyperammonemic rats.

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Ramakrishnan, Arumugam; Vijayakumar, Natesan

2017-10-01

Ammonia is a well-known neurotoxin that causes liver disease and urea cycle disorder. Excessive ammonia content in the blood leads to hyperammonemic condition and affects both excitatory and inhibitory neurotransmission including brain edema and coma. Naringin, a plant bioflavonoid present in various citrus fruits and mainly extracted from the grape fruit. This study was designed to assess the protective effect of naringin on ammonium chloride (NH 4 Cl) induced hyperammonemic rats. Experimental hyperammonemia was induced by intraperitoneal injections (i.p) of NH 4 Cl (100mg/kg body weight (b.w.)) thrice a week for 8 consecutive weeks. Hyperammonemic rats were treated with naringin (80mg/kg b.w.) via oral gavage. Naringin administration significantly augmented the level of blood ammonia and plasma urea. Naringin also upregulate the expression of urea cycle enzymes such as carbamoyl phosphate synthase I (CPS I) and ornithine transcarbamylase (OTC), arininosuccinate synthase (ASS), argininosuccinate lyase (ASL) and arginase I (ARG) and metabotropic glutamate receptors (mGluRs) such as mGluRs I and mGluRs V and down regulate the expression of inflammatory markers like tumor necrosis factor (TNF-α), nuclear factor kappa B (NF-kB), Interleukin-6 (IL-6), inducible nitric oxide synthase (iNOS). In addition, to this, the protective effect of naringin was also revealed through the immunohistochemical changes in tissues. Thus our present study result suggest that naringin modulates the expression of proteins involved in urea cycle pathway and suppresses the expression of inflammatory markers and acts as a potential agent to treat condition in rats. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Polymeric micelles for potentiated antiulcer and anticancer activities of naringin

Science.gov (United States)

Mohamed, Elham Abdelmonem; Abu Hashim, Irhan Ibrahim; Yusif, Rehab Mohammad; Shaaban, Ahmed Abdel Aziz; El-Sheakh, Ahmed Ramadan; Hamed, Mohammed Fawzy; Badria, Farid Abd Elreheem

2018-01-01

Naringin is one of the most interesting phytopharmaceuticals that has been widely investigated for various biological actions. Yet, its low water solubility, limited permeability, and suboptimal bioavailability limited its use. Therefore, in this study, polymeric micelles of naringin based on pluronic F68 (PF68) were developed, fully characterized, and optimized. The optimized formula was investigated regarding in vitro release, storage stability, and in vitro cytotoxicity vs different cell lines. Also, cytoprotection against ethanol-induced ulcer in rats and antitumor activity against Ehrlich ascites carcinoma in mice were investigated. Nanoscopic and nearly spherical 1:50 micelles with the mean diameter of 74.80±6.56 nm and narrow size distribution were obtained. These micelles showed the highest entrapment efficiency (EE%; 96.14±2.29). The micelles exhibited prolonged release up to 48 vs 10 h for free naringin. The stability of micelles was confirmed by insignificant changes in drug entrapment, particle size, and retention (%) (91.99±3.24). At lower dose than free naringin, effective cytoprotection of 1:50 micelles against ethanol-induced ulcer in rat model has been indicated by significant reduction in mucosal damage, gastric level of malondialdehyde, gastric expression of tumor necrosis factor-alpha, caspase-3, nuclear factor kappa-light-chain-enhancer of activated B cells, and interleukin-6 with the elevation of gastric reduced glutathione and superoxide dismutase when compared with the positive control group. As well, these micelles provoked pronounced antitumor activity assessed by potentiated in vitro cytotoxicity particularly against colorectal carcinoma cells and tumor growth inhibition when compared with free naringin. In conclusion, 1:50 naringin–PF68 micelles can be represented as a potential stable nanodrug delivery system with prolonged release and enhanced antiulcer as well as antitumor activities. PMID:29497294

Naringin Protects Against High Glucose-Induced Human Endothelial Cell Injury Via Antioxidation and CX3CL1 Downregulation

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Guilin Li

2017-08-01

Full Text Available Background/Aims: The induction of endothelial injury by hyperglycemia in diabetes has been widely accepted. Naringin is a bio-flavonoid. Some studies showed that naringin alleviates diabetic complications, but the exact mechanisms by which naringin improves diabetic anomalies are not yet fully understood. The aim of this research was to study the protective effect of naringin on high glucose-induced injury of human umbilical vein endothelial cells (HUVECs. Methods: HUVECs were cultured with or without high glucose in the absence or presence of naringin for 5 days. The expression of CX3CL1 was determined by quantitative real-time RT-PCR (qPCR and western blot. The cellular bioenergetic analysis oxygen consumption rate (OCR was measured with a Seahorse Bioscience XF analyzer. Results: The production of reactive oxygen species (ROS, the expression of CX3CL1 and the level of AKT phosphorylation were increased in HUVECs cultured with high glucose compared with controls. However, naringin rescued these increases in ROS production, CX3CL1 expression and AKT phosphorylation. Nitric oxide (NO production and OCR were lower in the high glucose group, and naringin restored the changes induced by high glucose. Molecular docking results suggested that Naringin might interact with the CX3CL1 protein. Conclusion: Naringin protects HUVECs from high-glucose-induced damage through its antioxidant properties by downregulating CX3CL1 and by improving mitochondrial function.

Instant controlled pressure drop technology and ultrasound assisted extraction for sequential extraction of essential oil and antioxidants.

Science.gov (United States)

Allaf, Tamara; Tomao, Valérie; Ruiz, Karine; Chemat, Farid

2013-01-01

The instant controlled pressure drop (DIC) technology enabled both the extraction of essential oil and the expansion of the matrix itself which improved solvent extraction. The sequential use of DIC and Ultrasound Assisted Extraction (UAE) triggered complementary actions materialized by supplementary effects. We visualized these combination impacts by comparing them to standard techniques: Hydrodistillation (HD) and Solvent Extraction (SE). First, the extraction of orange peel Essential Oils (EO) was achieved by HD during 4h and DIC process (after optimization) during 2 min; EO yields was 1.97 mg/g dry material (dm) with HD compared to 16.57 mg/g d m with DIC. Second, the solid residue was recovered to extract antioxidant compounds (naringin and hesperidin) by SE and UAE. Scanning electron microscope showed that after HD the recovered solid shriveled as opposite to DIC treatment which expanded the product structure. HPLC analyses showed that the best kinetics and yields of naringin and hesperidin extraction was when DIC and UAE are combined. Indeed, after 1h of extraction, DIC treated orange peels with UAE were 0.825 ± 1.6 × 10(-2)g/g of dry material (dm) for hesperidin and 6.45 × 10(-2) ± 2.3 × 10(-4)g/g d m for naringin compared to 0.64 ± 2.7 × 10(-2)g/g of dry material (dm) and 5.7 × 10(-2) ± 1.6 × 10(-3)g/g d m, respectively with SE. By combining DIC to UAE, it was possible to enhance kinetics and yields of antioxidant extraction. Copyright © 2012 Elsevier B.V. All rights reserved.

Pre-Harvest Dropped Kinnow ( Citrus reticulata Blanco) Waste Management through the Extraction of Naringin and Pectin from their Peels using Indigenous Resin

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Laxmi Deepak Bhatlu, M.; Katiyar, Prashant; Singh, Satya Vir; Verma, Ashok Kumar

2016-09-01

About 10-20 % kinnow fruits are dropped in preharvest stage which are waste and are problem to farmer as these create nuisance by rotting and insect rearing ground. The peels of these dropped fruits as well as peels from kinnow processing may be good source of naringin and pectin. Naringin is used in pharmaseutics while pectin is used in food industry. For recovery of naringin and pectn, peels of preharvest dropped kinnow fruits were boiled in water. The extract was passed through macroporus polymeric adsorbent resin Indion PA 800, naringin was adsorbed on it. The adsorbed naringin was desorbed with ethanol. This solution was passed through membrane filter and filtrate was evaporated to obtain naringin. The extract remaining after adsorption of naringin was used to recover pectin using acid extraction method. The recovery of naringin and pectin was about 52 and 58 % respectively. The naringin finally obtained had 91-93 % purity.

Possible regulation of LDL-receptor by naringenin in HepG2 ...

African Journals Online (AJOL)

However, after 24h incubation with 200μM naringenin the gene expression activities of all the SREBP-1a, -1c, -2 and LDLr promoterconstructs were increased significantly. The effects of both 200μM naringenin on elevating LDLr mRNA are possibly due to regulation of gene transcription by SREBP-la and SREBP-2.

Naringin promotes osteogenic differentiation of bone marrow stromal cells by up-regulating Foxc2 expression via the IHH signaling pathway.

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Lin, Fei-Xiang; Du, Shi-Xin; Liu, De-Zhong; Hu, Qin-Xiao; Yu, Guo-Yong; Wu, Chu-Cheng; Zheng, Gui-Zhou; Xie, Da; Li, Xue-Dong; Chang, Bo

2016-01-01

Naringin is an active compound extracted from Rhizoma Drynariae, and studies have revealed that naringin can promote proliferation and osteogenic differentiation of bone marrow stromal cells (BMSCs). In this study, we explored whether naringin could promote osteogenic differentiation of BMSCs by upregulating Foxc2 expression via the Indian hedgehog (IHH) signaling pathway. BMSCs were cultured in basal medium, basal medium with naringin, osteogenic induction medium, osteogenic induction medium with naringin and osteogenic induction medium with naringin in the presence of the IHH inhibitor cyclopamine (CPE). We examined cell proliferation by using a WST-8 assay, and differentiation by Alizarin Red S staining (for mineralization) and alkaline phosphatase (ALP) activity. In addition, we detected core-binding factor α1 (Cbfα1), osteocalcin (OCN), bone sialoprotein (BSP), peroxisome proliferation-activated receptor gamma 2 (PPARγ2) and Foxc2 expression by using RT-PCR. We also determined Foxc2 and IHH protein levels by western blotting. Naringin increased the mineralization of BMSCs, as shown by Alizarin red S assays, and induced ALP activity. In addition, naringin significantly increased the mRNA levels of Foxc2, Cbfα1, OCN, and BSP, while decreasing PPARγ2 mRNA levels. Furthermore, the IHH inhibitor CPE inhibited the osteogenesis-potentiating effects of naringin. Naringin increased Foxc2 and stimulated the activation of IHH, as evidenced by increased expression of proteins that were inhibited by CPE. Our findings indicate that naringin promotes osteogenic differentiation of BMSCs by up-regulating Foxc2 expression via the IHH signaling pathway.

Naringin attenuates granule cell dispersion in the dentate gyrus in a mouse model of temporal lobe epilepsy.

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Jang, Hannah; Jeong, Kyoung Hoon; Kim, Sang Ryong

2016-07-01

Morphological abnormalities of the dentate gyrus (DG) are an important phenotype in the hippocampus of patients with temporal lobe epilepsy. We recently reported that naringin, a bioflavonoid in grapefruit and citrus fruits, exerts beneficial effects in the kainic acid (KA) mouse model of epilepsy. We found that naringin treatment reduced seizure activities and decreased autophagic stress and neuroinflammation in the hippocampus following in vivo lesion with KA. However, it remains unclear whether naringin may also attenuate seizure-induced morphological changes in the DG, collectively known as granule cell dispersion (GCD). To clarify whether naringin treatment reduces GCD, we evaluated the effects of intraperitoneal injection of naringin on GCD and activation of mammalian target of rapamycin complex 1 (mTORC1), an important regulator of GCD, following intrahippocampal injection of KA. Our results showed that naringin treatment significantly reduced KA-induced GCD and mTORC1 activation, which was confirmed by assessing the phosphorylated form of the mTORC1 substrate, 4E-BP1, in the hippocampus. These results suggest that naringin treatment may help prevent epilepsy-induced hippocampal injury by inhibiting mTORC1 activation and thereby reducing GCD in the hippocampus in vivo. Copyright © 2016 Elsevier B.V. All rights reserved.

Copper (II) and zinc (II) complexes with flavanone derivatives: Identification of potential cholinesterase inhibitors by on-flow assays.

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Sarria, André Lucio Franceschini; Vilela, Adriana Ferreira Lopes; Frugeri, Bárbara Mammana; Fernandes, João Batista; Carlos, Rose Maria; da Silva, Maria Fátima das Graças Fernandes; Cass, Quezia Bezerra; Cardoso, Carmen Lúcia

2016-11-01

Metal chelates strongly influence the nature and magnitude of pharmacological activities in flavonoids. In recent years, studies have shown that a promising class of flavanone-metal ion complexes can act as selective cholinesterase inhibitors (ChEIs), which has led our group to synthesize a new series of flavanone derivatives (hesperidin, hesperetin, naringin, and naringenin) complexed to either copper (II) or zinc (II) and to evaluate their potential use as selective ChEIs. Most of the synthesized complexes exhibited greater inhibitory activity against acetylcholinesterase (AChE) than against butyrylcholinesterase (BChE). Nine of these complexes constituted potent, reversible, and selective ChEIs with inhibitory potency (IC 50 ) and inhibitory constant (K i ) ranging from 0.02 to 4.5μM. Copper complexes with flavanone-bipyridine derivatives afforded the best inhibitory activity against AChE and BChE. The complex Cu(naringin)(2,2'-bipyridine) (11) gave IC 50 and K i values of 0.012±0.002 and 0.07±0.01μM for huAChE, respectively, which were lower than the inhibitory values obtained for standard galanthamine (IC 50 =206±30.0 and K i =126±18.0μM). Evaluation of the inhibitory activity of this complex against butyrylcholinesterase from human serum (huBChE) gave IC 50 and K i values of 8.0±1.4 and 2.0±0.1μM, respectively. A Liquid Chromatography-Immobilized Capillary Enzyme Reactor by UV detection (LC-ICER-UV) assay allowed us to determine the IC 50 and K i values and the type of mechanism for the best inhibitors. Copyright © 2016 Elsevier Inc. All rights reserved.

Randomized clinical trial on the efficacy of hesperidin 2S on validated cardiovascular biomarkers in healthy overweight individuals.

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Salden, Bouke N; Troost, Freddy J; de Groot, Eric; Stevens, Yala R; Garcés-Rimón, Marta; Possemiers, Sam; Winkens, Bjorn; Masclee, Ad A

2016-12-01

Endothelial dysfunction (ED) is involved in the development of atherosclerosis. Hesperidin, a citrus flavonoid with antioxidant and other biological properties, potentially exerts beneficial effects on endothelial function (EF). We investigated the effect of hesperidin 2S supplementation on EF in overweight individuals. This was a randomized, double-blind, placebo-controlled study in which 68 individuals were randomly assigned to receive hesperidin 2S (450 mg/d) or a placebo for 6 wk. At baseline and after 6 wk of intervention, flow-mediated dilation (FMD), soluble vascular adhesion molecule-1 (sVCAM-1), soluble intracellular adhesion molecule-1 (sICAM-1), soluble P-selectin (sP-selectin), systolic blood pressure (SBP), and diastolic blood pressure (DBP) were assessed. Acute, reversible ED was induced by intake of a high-fat meal (HFM). A second FMD scan was performed 2 h postprandially, and adhesion molecules were assessed 2 and 4 h postprandially. An additional exploratory analysis was performed in subjects with baseline FMD ≥3%. No significant change in fasting or postprandial FMD was observed after 6 wk of hesperidin intake compared with placebo intake. However, there was a trend for a reduction of sVCAM-1, sICAM-1, sP-selectin, SBP, and DBP after 6 wk of hesperidin treatment. In the FMD ≥3% group, hesperidin protected individuals from postprandial ED (P = 0.050) and significantly downregulated sVCAM-1 and sICAM-1 (all P ≤ 0.030). The results reported in the current article were not adjusted for multiplicity. Six weeks of consumption of hesperidin 2S did not improve basal or postprandial FMD in our total study population. There was a tendency toward a reduction of adhesion molecules and a decrease in SBP and DBP. Further exploratory analyses revealed that, in subjects with baseline FMD ≥3%, hesperidin 2S improved ED after an HFM and reduced adhesion molecules. These results indicate the cardiovascular health benefits of hesperidin 2S in overweight and

Radioimmunoassay for the citrus bitter principle, naringin, and related flavonoid-7-O-neohesperidosides

International Nuclear Information System (INIS)

Jourdan, P.S.; Weiler, E.W.; Mansell, R.L.

1982-01-01

An immunoassay for the citrus bitter principle, naringin, and related flavonoid-7-O-neohesperidosides is reported. The assay detects ca. 2 ng of naringin and can be used to quantify this compound in the parts per billion (ppb) range in crude grapefruit juice and extracts of other plant tissues. The antiserum used is highly reactive with the 2-rhamnosyl-1-glucopyranose at the C-7 position but not with e.g. the isomeric 6-rhamnosyl-1-glucopyranose moiety and can, thus, be used to identify the stereochemistry of this disaccharide moiety at the C-7 position of flavanoids. The assay involves a directly iodinated naringin-[ 125 I] as immunotracer. (orig.)

Effect of ethylene on naringin, narirutin and nootkatone accumulation in grapefruit.

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Puig, D G; Pérez, M L; Fuster, M D; Ortuño, A; Sabater, F; Porras, I; Lidón, A G; Del Río, J A

1995-06-01

This paper studies the effect of different concentrations of ethephon on the levels of the sesquiterpene, nootkatone, and of the flavanones, naringin and narirutin, in grapefruit fruits. The results show that nootkatone synthesis and/or accumulation was stimulated by all the concentrations of ethephon assayed, while the levels of naringin and narirutin in the rind diminished. These results open up new perspectives concerning the possible regulation of the secondary metabolism of the plants.

Effects of Hesperidin as a Radioprotector on Apoptosis in Rat Peripheral Blood Lymphocytes after Gamma Radiation

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Fardid R.

2016-12-01

Full Text Available Introduction: Hesperidin (HES, as the most abundant flavonoid existing in the citrus, is widely used by human daily. The radio-protective effects of Hesperidin have been confirmed in various measurement systems. This study aimed to evaluate the effects of Hesperidin on the changes in the apoptosis level and expression of apoptotic genes target (bax, bcl-2 and ration of bax/bcl-2 in the peripheral blood lymphocytes of male rats after gamma radiation. Materials and Methods: 64 male rats were divided into eight groups: Control, HES (100 mg/kg b.w, orally, 7 days, whole body irradiation with 2 and 8Gy, preadministrated with 50 and 100 mg/kg body weight of Hesperidin for 7 days before irradiation with 2 and 8 Gy. 24 hours after radiation, apoptotic lymphocytes were evaluated using PE Annexin V Apoptosis detection I kit and the levels of mRNA for bax and bcl-2 were evaluated by real time reverse transcription polymerase chain reaction. Results: A significant reduction in apoptosis of the lymphocytes was demonstrated in group animals receiving 8 Gy compared to the group which received 2 Gy irradiation (p<0.0001. However, apoptosis significantly increased in group of rats who received Hesp before irradiation (p<0.05. The increase of apoptosis by Hesperidin administration can be attributed to the decreased expression of bax and significantly reduced expression of bcl-2 and finally increasing the ration of bax/bcl-2. Conclusion: The results suggest that administration of 50 and 100 mg/kg of Hesperidin induces apoptotic effects by changing expression level of bax, bcl-2 and also the ratio of bax/bcl2.

Hesperidin, a citrus bioflavonoid, alleviates trichloroethylene-induced oxidative stress in Drosophila melanogaster.

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Abolaji, Amos Olalekan; Babalola, Oluwatoyin Victoria; Adegoke, Abimbola Kehinde; Farombi, Ebenezer Olatunde

2017-10-01

Trichloroethylene (TCE) is a chlorinated organic pollutant of groundwater with diverse toxic effects in animals and humans. Here, we investigated the ameliorative role of hesperidin, a citrus bioflavonoid on TCE-induced toxicity in Drosophila melanogaster. Four groups of D. melanogaster (50 flies/vial, with 5 vials/group) were exposed to ethanol (2.5%, control), HSP (400mg/10g diet), TCE (10μM/10g diet) and TCE (10μM/10g diet)+HSP (400mg/10g diet) respectively in the diet for 5days. Then, selected oxidative stress and antioxidant markers were evaluated. The results showed that TCE significantly increased the level of reactive oxygen species (ROS) and inhibited catalase, glutathione S-transferase and acetylcholinesterase (AChE) activities with concurrent depletion of total thiol level. However, co-administration of TCE and hesperidin mitigated TCE-induced depletion of antioxidants, and restored ROS level and AChE activity in the flies (p<0.05). Overall, hesperidin offered protective potency on TCE-induced oxidative stress in the flies via anti-oxidative mechanism. Copyright © 2017 Elsevier B.V. All rights reserved.

Hesperidin Protects against Acute Alcoholic Injury through Improving Lipid Metabolism and Cell Damage in Zebrafish Larvae

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Zhenting Zhou

2017-01-01

Full Text Available Alcoholic liver disease (ALD is a series of abnormalities of liver function, including alcoholic steatosis, steatohepatitis, and cirrhosis. Hesperidin, the major constituent of flavanone in grapefruit, is proved to play a role in antioxidation, anti-inflammation, and reducing multiple organs damage in various animal experiments. However, the underlying mechanism of resistance to alcoholic liver injury is still unclear. Thus, we aimed to investigate the protective effects of hesperidin against ALD and its molecular mechanism in this study. We established an ALD zebrafish larvae model induced by 350 mM ethanol for 32 hours, using wild-type and transgenic line with liver-specific eGFP expression Tg (lfabp10α:eGFP zebrafish larvae (4 dpf. The results revealed that hesperidin dramatically reduced the hepatic morphological damage and the expressions of alcohol and lipid metabolism related genes, including cyp2y3, cyp3a65, hmgcra, hmgcrb, fasn, and fads2 compared with ALD model. Moreover, the findings demonstrated that hesperidin alleviated hepatic damage as well, which is reflected by the expressions of endoplasmic reticulum stress and DNA damage related genes (chop, gadd45αa, and edem1. In conclusion, this study revealed that hesperidin can inhibit alcoholic damage to liver of zebrafish larvae by reducing endoplasmic reticulum stress and DNA damage, regulating alcohol and lipid metabolism.

Protective Effect of Hesperetin and Naringenin against Apoptosis in Ischemia/Reperfusion-Induced Retinal Injury in Rats

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Selcuk Kara

2014-01-01

Full Text Available Purpose. Hesperetin and naringenin are naturally common flavonoids reported to have antioxidative effects. This study was performed to investigate whether either hesperetin or naringenin has a protective effect against apoptosis on retinal ischemia/reperfusion (I/R injury. Methods. Retinal I/R was induced by increasing the intraocular pressure to 150 mmHg for 60 minutes. Thirty-three male Wistar albino rats were randomised into 5 groups named control, I/R + sham, I/R + solvent (DMSO, I/R + hesperetin, and I/R + naringenin. Animals were given either hesperetin, naringenin, or the solvent intraperitoneally immediately following reperfusion. Thickness of retinal layers and retinal cell apoptosis were detected by histological analysis, tunel assay, and immunohistochemistry assay. Results. Hesperetin and naringenin attenuated the I/R-induced apoptosis of retinal cells in the inner and outer nuclear cells of the rat retina. Retinal layer thickness of the naringenin treatment group was significantly thicker than that of the hesperetin, sham, and solvent groups (P<0.05. Conclusions. Hesperetin and naringenin can prevent harmful effects induced by I/R injury in the rat retina by inhibiting apoptosis of retinal cells, which suggests that those flavanones have a therapeutic potential for the protection of ocular ischemic diseases.

Modulation of the growth and metabolic response of cyanobacteria by the multifaceted activity of naringenin.

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Beata Żyszka

Full Text Available The interactions between the plant-derived bioflavonoid, naringenin, and prokaryotic microalgae representatives (cyanobacteria, were investigated with respect to its influence on the growth and metabolic response of these microorganisms. To achieve reliable results, the growth of cyanobacteria was determined based on measurements of chlorophyll content, morphological changes were assessed through microscopic observations, and the chemical response of cells was determined using liquid and gas chromatography (HPLC; GC-FID. The results show that micromolar levels of naringenin stimulated the growth of cyanobacteria. Increased growth was observed for halophilic strains at naringenin concentrations below 40 mg L-1, and in freshwater strains at concentrations below 20 mg L-1. The most remarkable stimulation was observed for the freshwater species Nostoc muscorum, which had a growth rate that was up to 60% higher than in the control. When naringenin was examined at concentrations above 40 mg L-1, the growth of the tested microorganisms was inhibited. Simultaneously, an intensive excretion of exopolysaccharides was observed. Microscopic observations strongly suggest that these effects resulted from a structural disturbance of cyanobacterial cell walls that was exerted by naringenin. This phenomenon, in combination with the absorption of naringenin into cell wall structures, influenced cell permeability and thus the growth of bacteria. Fortunately, almost all the naringenin added to the culture was incorporated into to cell substructures and could be recovered through extraction, raising the possibility that this modulator could be recycled.

Hesperidin protects against cyclophosphamide-induced hepatotoxicity by upregulation of PPARγ and abrogation of oxidative stress and inflammation.

Science.gov (United States)

Mahmoud, Ayman M

2014-09-01

The most important reason for the non-approval and withdrawal of drugs by the Food and Drug Administration is hepatotoxicity. Therefore, this study was undertaken to evaluate the protective effects of hesperidin against cyclophosphamide (CYP)-induced hepatotoxicity in Wistar rats. The rats received a single intraperitoneal dose of CYP of 200 mg/kg body mass, followed by treatment with hesperidin, orally, at doses of 25 and 50 mg/kg for 11 consecutive days. CYP induced hepatic damage, as evidenced by the significantly elevated levels of serum pro-inflammatory cytokines, serum transaminases, liver lipid peroxidation, and nitric oxide. As a consequence, there was reduced glutathione content, and the activities of the antioxidant enzymes superoxide dismutase, catalase, and glutathione peroxidase, were markedly reduced. In addition, CYP administration induced a considerable downregulation of peroxisome proliferator activated receptor gamma (PPARγ) and upregulation of nuclear factor-kappa B (NF-κB) and inducible nitric oxide synthase (iNOS) mRNA expression. Hesperidin, in a dose-dependent manner, rejuvenated the altered markers to an almost normal state. In conclusion, hesperidin showed a potent protective effect against CYP-induced oxidative stress and inflammation leading to hepatotoxicity. The study suggests that hesperidin exerts its protective effect against CYP-induced hepatotoxicity through upregulation of hepatic PPARγ expression and abrogation of inflammation and oxidative stress.

Grapefruit Derived Flavonoid Naringin Improves Ketoacidosis and Lipid Peroxidation in Type 1 Diabetes Rat Model.

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Alfred N Murunga

Full Text Available Hypoglycemic effects of grapefruit juice are well known but the effects of naringin, its main flavonoid on glucose intolerance and metabolic complications in type 1 diabetes are not known.To investigate the effects of naringin on glucose intolerance, oxidative stress and ketonemia in type 1 diabetic rats.Sprague-Dawley rats divided into 5 groups (n = 7 were orally treated daily with 3.0 ml/kg body weight (BW/day of distilled water (group 1 or 50 mg/kg BW of naringin (groups 2 and 4, respectively. Groups 3, 4 and 5 were given a single intra-peritoneal injection of 60 mg/kg BW of streptozotocin to induce diabetes. Group 3 was further treated with subcutaneous insulin (4.0 IU/kg BW twice daily, respectively.Stretozotocin (STZ only-treated groups exhibited hyperglycemia, polydipsia, polyuria, weight loss, glucose intolerance, low fasting plasma insulin and reduced hepatic glycogen content compared to the control group. Furthermore they had significantly elevated Malondialdehyde (MDA, acetoacetate, β-hydroxybutyrate, anion gap and significantly reduced blood pH and plasma bicarbonate compared to the control group. Naringin treatment significantly improved Fasting Plasma Insulin (FPI, hepatic glycogen content, malondialdehyde, β-hydroxybutyrate, acetoacetate, bicarbonate, blood pH and anion gap but not Fasting Blood Glucose (FBG compared to the STZ only-treated group.Naringin is not hypoglycemic but ameliorates ketoacidosis and oxidative stress. Naringin supplements could therefore mitigate complications of diabetic ketoacidosis.

Hesperidin suppresses the migration and invasion of non-small cell lung cancer cells by inhibiting the SDF-1/CXCR-4 pathway.

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Xia, Rongmu; Xu, Gang; Huang, Yue; Sheng, Xin; Xu, Xianlin; Lu, Hongling

2018-05-15

The present study aimed to investigate the ability of hesperidin to suppress the migration and invasion of A549 cells, and to investigate the role of the SDF-1/CXCR-4 cascade in this suppression. We performed a Transwell migration assay to measure the migratory capability of A549 cells treated with 0.5% DMSO, SDF-1α, AMD3100 or hesperidin. The SDF-1 level in the culture medium was determined by an enzyme-linked immunosorbent assay (ELISA) to detect whether different concentrations of hesperidin affected SDF-1 secretion. A wound-healing assay was performed to determine the effects of different concentrations of hesperidin on the migration inhibition of A549, H460 and H1975 cells. Additionally, the effect of various hesperidin concentrations on the rate of A549 cell invasion and migration was examined with and without Matrigel in Transwell assays, respectively. Western blot analysis was used to evaluate the protein levels of CXCR-4, MMP-9, CK-19, Vimentin, p65, p-p65, p-IκB, IκB, p-Akt and Akt. RT-qPCR was used to detect the mRNA levels of CXCR-4, MMP-9, CK-19, Vimentin, p65, IκB, SDF-1 and Akt. The Transwell migration assay indicated that SDF-1α promoted A549 cell migration, while AMD3100 and hesperidin significantly inhibited the migratory capability. The wound-healing assay demonstrated that hesperidin treatment significantly reduced the rate of wound closure compared with the control group in a dose-dependent manner. Similarly, the migration and invasive abilities of A549 cells, H460 and H1975 cells treated with hesperidin were significantly decreased compared with the control group. The ELISA data suggested that hesperidin attenuated the secretion of SDF-1 from A549 cells in a dose-dependent manner. Furthermore, western blot analysis indicated that SDF-1α treatment significantly increased the levels of CXCR-4, p-p65, p-IκB and p-Akt in A549 cells. In contrast, AMD3100 or hesperidin reversed the effect induced by SDF-1α through decreasing the expression

Kappa-opioid receptors mediate the antidepressant-like activity of hesperidin in the mouse forced swimming test.

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Filho, Carlos B; Del Fabbro, Lucian; de Gomes, Marcelo G; Goes, André T R; Souza, Leandro C; Boeira, Silvana P; Jesse, Cristiano R

2013-01-05

The opioid system has been implicated as a contributing factor for major depression and is thought to play a role in the mechanism of action of antidepressants. This study investigated the involvement of the opioid system in the antidepressant-like effect of hesperidin in the mouse forced swimming test. Our results demonstrate that hesperidin (0.1, 0.3 and 1 mg/kg; intraperitoneal) decreased the immobility time in the forced swimming test without affecting locomotor activity in the open field test. The antidepressant-like effect of hesperidin (0.3 mg/kg) in the forced swimming test was prevented by pretreating mice with naloxone (1 mg/kg, a nonselective opioid receptor antagonist) and 2-(3,4-dichlorophenyl)-Nmethyl-N-[(1S)-1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl] acetamide (DIPPA (1 mg/kg), a selective κ-opioid receptor antagonist), but not with naloxone methiodide (1 mg/kg, a peripherally acting opioid receptor antagonist), naltrindole (3 mg/kg, a selective δ-opioid receptor antagonist), clocinnamox (1 mg/kg, a selective μ-opioid receptor antagonist) or caffeine (3 mg/kg, a nonselective adenosine receptor antagonist). In addition, a sub-effective dose of hesperidin (0.01 mg/kg) produced a synergistic antidepressant-like effect in the forced swimming test when combined with a sub-effective dose of morphine (1 mg/kg). The antidepressant-like effect of hesperidin in the forced swimming test on mice was dependent on its interaction with the κ-opioid receptor, but not with the δ-opioid, μ-opioid or adenosinergic receptors. Taken together, these results suggest that hesperidin possesses antidepressant-like properties and may be of interest as a therapeutic agent for the treatment of depressive disorders. Published by Elsevier B.V.

Genome wide transcriptional profiling of Herbaspirillum seropedicae SmR1 grown in the presence of naringenin.

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Tadra-Sfeir, Michelle Z; Faoro, Helisson; Camilios-Neto, Doumit; Brusamarello-Santos, Liziane; Balsanelli, Eduardo; Weiss, Vinicius; Baura, Valter A; Wassem, Roseli; Cruz, Leonardo M; De Oliveira Pedrosa, Fábio; Souza, Emanuel M; Monteiro, Rose A

2015-01-01

Herbaspirillum seropedicae is a diazotrophic bacterium which associates endophytically with economically important gramineae. Flavonoids such as naringenin have been shown to have an effect on the interaction between H. seropedicae and its host plants. We used a high-throughput sequencing based method (RNA-Seq) to access the influence of naringenin on the whole transcriptome profile of H. seropedicae. Three hundred and four genes were downregulated and seventy seven were upregulated by naringenin. Data analysis revealed that genes related to bacterial flagella biosynthesis, chemotaxis and biosynthesis of peptidoglycan were repressed by naringenin. Moreover, genes involved in aromatic metabolism and multidrug transport efllux were actived.

Kinetic study on the inhibition of xanthine oxidase by acylated derivatives of flavonoids synthesised enzymatically.

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de Araújo, Maria Elisa Melo Branco; Franco, Yollanda Edwirges Moreira; Alberto, Thiago Grando; Messias, Marcia Cristina Fernandes; Leme, Camila Wielewski; Sawaya, Alexandra Christine Helena Frankland; Carvalho, Patricia de Oliveira

2017-12-01

Studies have reported that flavonoids inhibit xanthine oxidase (XO) activity; however, poor solubility and stability in lipophilic media limit their bioavailability and applications. This study evaluated the kinetic parameters of XO inhibition and partition coefficients of flavonoid esters biosynthesised from hesperidin, naringin, and rutin via enzymatic acylation with hexanoic, octanoic, decanoic, lauric, and oleic acids catalysed by Candida antarctica lipase B (CALB). Quantitative determination by ultra-high performance liquid chromatography-mass spectrometry (UHPLC-MS) showed higher conversion yields (%) for naringin and rutin esters using acyl donors with 8C and 10C. Rutin decanoate had higher partition coefficients (0.95), and naringin octanoate and naringin decanoate showed greater inhibitory effects on XO (IC 50 of 110.35 and 117.51 μM, respectively). Kinetic analysis showed significant differences (p flavonoids before and after acylation regarding K m values, whereas the values for V max were the same, implying the competitive nature of XO inhibition.

Genome Wide Transcriptional Profiling of Herbaspirillum seropedicae SmR1 Grown in the presence of naringenin

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Michele Zibetti Tadra-Sfeir

2015-05-01

Full Text Available Herbaspirillum seropedicae is a diazotrophic bacterium which associates endophytically with economically important gramineae. Flavonoids such as naringenin, have been shown to have an effect on the interaction between H. seropedicae and its host plants. We used a high-throughput sequencing based method (RNA-Seq to access the influence of naringenin on the whole transcriptome profile of H. seropedicae. Three hundred and four genes were downregulated and seventy seven were upregulated by naringenin. Data analysis revealed that genes related to bacterial flagella biosynthesis, chemotaxis and biosynthesis of peptidoglycan were repressed by naringenin. Moreover, genes involved in aromatic metabolism and multidrug transport efllux were actived.

The citrus flavanone naringenin impairs dengue virus replication in human cells

OpenAIRE

Frabasile, Sandra; Koishi, Andrea Cristine; Kuczera, Diogo; Silveira, Guilherme Ferreira; Verri, Waldiceu Aparecido; Duarte dos Santos, Claudia Nunes; Bordignon, Juliano

2017-01-01

Dengue is one of the most significant health problems in tropical and sub-tropical regions throughout the world. Nearly 390 million cases are reported each year. Although a vaccine was recently approved in certain countries, an anti-dengue virus drug is still needed. Fruits and vegetables may be sources of compounds with medicinal properties, such as flavonoids. This study demonstrates the anti-dengue virus activity of the citrus flavanone naringenin, a class of flavonoid. Naringenin prevente...

Development and validation of spectrofluorimetric and LC–MS/MS methods for the determination of hesperidin in human plasma and pharmaceutical forms

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Pavun Leposava A.

2012-01-01

Full Text Available The spectrofluorometric method, based on fluorescence properties of aluminium (III–hesperidin complex, for the determination of hesperidin in human plasma and pharmaceutical forms has been developed and validated. The complex shows strong emission in the presence of surfactant betain sulfonate SB 12 at 476 nm with excitation at 390 nm. Linearity range in pharmaceutical forms of hesperidin was 0.06 – 24.4 μg mL-1 with LOD 0.016 μg mL-1 and LOQ 0.049 μg mL-1. Recovery values in the range 99.3 – 99.7% indicate good accuracy of the method. A linear dependence of the intensity of fluorescence of the complex on the concentration of hesperidin in plasma was obtained in concentration range from 0.1 – 12.2 μg mL-1. The LOD was 0.032 μg mL-1 while LOQ was 0.096 μg mL-1. Recovery values were in the range 98.4 – 99.8%. The reliability of the method was checked by LC-MS/MS method for plasma samples and HPLC/UV method for tablets with direct determination of hesperidin after separation. Linearity range in determination of hesperidin in pharmaceutical forms was obtained in the range from 0.05 to 10.00 μg mL-1. The LOD was 0.01 μg mL-1 and LOQ was 0.03 μg mL-1. Linearity range in plasma determination of hesperidin was 0.02 – 10.00 μg mL-1 with LOD 0.005 μg mL-1 and LOQ 0.015 μg mL-1. Good agreement between two methods indicate the usability of the proposed spectroflurometric method for the simple, precise and accurate determination of hesperidin in clinical and quality control laboratories.

Naringin ameliorates metabolic syndrome by activating AMP-activated protein kinase in mice fed a high-fat diet.

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Pu, Peng; Gao, Dong-Mei; Mohamed, Salim; Chen, Jing; Zhang, Jing; Zhou, Xiao-Ya; Zhou, Nai-Jing; Xie, Jing; Jiang, Hong

2012-02-01

Metabolic syndrome is a low-grade inflammatory state in which oxidative stress is involved. Naringin, isolated from the Citrussinensis, is a phenolic compound with anti-oxidative and anti-inflammatory activities. The aim of this study was to explore the effects of naringin on metabolic syndrome in mice. The animal models, induced by high-fat diet in C57BL/6 mice, developed obesity, dyslipidemia, fatty liver, liver dysfunction and insulin resistance. These changes were attenuated by naringin. Further investigations revealed that the inhibitory effect on inflammation and insulin resistance was mediated by blocking activation of the MAPKs pathways and by activating IRS1; the lipid-lowering effect was attributed to inhibiting the synthesis way and increasing fatty acid oxidation; the hypoglycemic effect was due to the regulation of PEPCK and G6pase. The anti-oxidative stress of naringin also participated in the improvement of insulin resistance and lipogenesis. All of these depended on the AMPK activation. To confirm the results of the animal experiment, we tested primary hepatocytes exposed to high glucose system. Naringin was protective by phosphorylating AMPKα and IRS1. Taken together, these results suggested that naringin protected mice exposed to a high-fat diet from metabolic syndrome through an AMPK-dependent mechanism involving multiple types of intracellular signaling and reduction of oxidative damage. Copyright © 2011 Elsevier Inc. All rights reserved.

Abatement by Naringenin of Doxorubicin-Induced Cardiac Toxicity in Rats

International Nuclear Information System (INIS)

Arafa, H.M.; Abd-Ellah, M.F.; Hafez, H.F.

2005-01-01

Doxorubicin is one of the most active cytotoxic agents in current use. It has proven efficacy in various malignancies either alone or combined with other cytocidal agents. The clinical usefulness of the anthracycline drug has been precluded by cardiac toxicity. Many therapeutic interventions have been attempted to improve the therapeutic benefits of the drug. Few, however, have been efficacious in this setting. Purpose: We have addressed in the current study the possible protective effects of naringenin, a flavonoid known to have anti-oxidant properties, on doxorubicin induced cardiac toxicity in male Swiss albino rats. Methods: Forty male Swiss albino rats were used in this study. Naringenin (25 mg/kg body weight) was administered daily by gavage for 7 consecutive days before a cumulative single dose of doxorubicin (15 mg/kg body weight, ip). Doxorubicin induced marked biochemical alterations characteristic of cardiac toxicity including, elevated activities of serum total lactate dehydrogenase (LDH) and creatine phosphokinase (CPK), enhanced lipid peroxidation measured as malonaldehyde (MDA). The anthracycline drug has also reduced the cardiac enzymatic activities of superoxide dismutase (SOD), glutathione-Stransferase (GST) and catalase (CAT). Besides, it reduced significantly the reduced glutathione (GSH) level, but it increased the total NO content in heart tissue. Prior administration of naringenin ahead of doxorubicin challenge ameliorated all these biochemical markers. Taken together, one could conclude that naringenin has a protective role in the abatement of doxorubicin-induced cardiac toxicity that resides, at least in part, on its anti-radical effects and regulatory role on NO production

Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients.

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Bailey, D G; Dresser, G K; Kreeft, J H; Munoz, C; Freeman, D J; Bend, J R

2000-11-01

To determine whether unprocessed grapefruit can cause a drug interaction, whether the active ingredients are naturally occurring, and whether specific furanocoumarins or flavonoids are involved. The oral pharmacokinetics of felodipine and its dehydrofelodipine metabolite were determined after administration of felodipine 10 mg extended-release tablet with 250 mL commercial grapefruit juice, homogenized grapefruit segments, or extract of segment-free parts equivalent to one unprocessed fruit or water in a randomized four-way crossover study. Inhibition of recombinant CYP3A4 by furanocoumarins (bergamottin, 6',7'-epoxybergamottin, 6',7'-dihydroxybergamottin) and flavonoids (naringenin optical isomers) was determined. Furanocoumarin and naringenin precursor (naringin) concentrations were measured in each grapefruit treatment. Felodipine AUC with commercial grapefruit juice, grapefruit segments, or grapefruit extract was on average 3-fold higher than that with water. Felodipine peak concentration was higher, but the half-life was unchanged. The dehydrofelodipine/felodipine AUC ratio was reduced. The furanocoumarins produced mechanism-based and competitive inhibition of CYP3A4. Bergamottin was the most potent mechanism-based inhibitor. Naringenin isomers produced only competitive inhibition. Bergamottin, 6',7'-dihydroxybergamottin, and naringin concentrations varied among grapefruit treatments but were sufficient to inhibit markedly in vitro CYP3A4 activity. Unprocessed grapefruit can cause a drug interaction with felodipine. The active ingredients are naturally occurring in the grapefruit. Bergamottin is likely important in drug interactions with commercial grapefruit juice. 6',7'-Dihydroxybergamottin and naringin may be more important in grapefruit segments because they are present in higher concentrations. Any therapeutic concern for a drug interaction with commercial grapefruit juice should now be extended to include whole fruit and possibly confectioneries made

Development of composition containing hesperidin for protection against radio-cellular damage

Energy Technology Data Exchange (ETDEWEB)

Park, Sang Hyun; Jang, Beom Su

2013-09-15

Now a days, ionizing radiation finds a broad range of applications in various industries. Ionizing radiation is also a powerful weapon in the treatment of various cancers. Despite has a good therapeutic index, radiotherapy can be caused tissue injury to normal tissues in long-term cancer survivors. Therefore, there is an urgent need to protect humans form the side effects of radiation exposure. The hesperidin was found to offer protection and treatment of disease caused oxidative stress against ionizing radiation for people and health professional undergoing radiological treatment. In this study, we develop the hesperidin formulation that can be mixed with other food and various drugs formulation. Therefore, it can be easily applied as a radiation protective agent for human. In addition, this emulsion technique can be expanded to others formula application.

Effect of Naringenin (A naturally occurring flavanone) Against Pilocarpine-induced Status Epilepticus and Oxidative Stress in Mice

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Shakeel, Sheeba; Rehman, Muneeb U.; Tabassum, Nahida; Amin, Umar; Mir, Manzoor ur Rahman

2017-01-01

Background: Epilepsy is a disorder of the central nervous system characterized by recurrent seizures. It is a very common disease in which approximately 30% of patients do not respond favourably to treatment with anticonvulsants. Oxidative stress is associated with neuronal damage arising from epileptic seizures. The present study investigated the effects of naringenin in pilocarpine-induced epilepsy in mice. Naringenin, one of the most frequently occurring flavanone in citrus fruits, was evaluated for its shielding effect against the pilocarpine induced behavioural, oxidative and histopathological alterations in rodent model of epilepsy. Methodology: Epilepsy was induced by giving pilocarpine (300mg/kg) and sodium valproate (300mg/kg) was given as standard anti-epileptic drug Pilocarpine was administered (300 mg /kg body weight) intraperitoneally to the mice on 15th day while naringenin was administered orally (20 and 40 mg/kg body weight) for 15 days prior to administration of pilocarpine. Results: The intraperitoneal administration of pilocarpine enhanced lipid peroxidation, caused reduction in antioxidant enzymes, viz., catalase, superoxide dismutase and glutathione reductase. Treatment of mice orally with naringenin (20 mg/kg body weight and 40 mg/kg body weight) resulted in a significant decrease in lipid peroxidation. There was significant recovery of glutathione content and all the antioxidant enzymes studied. Also in case of behavioural parameters studied, naringenin showed decrease in seizure severity. All these changes were supported by histological observations, which revealed excellent improvement in neuronal damage. Conclusion: The higher dose of naringenin was more potent in our study and was comparable to the standard drug (sodium valproate) in effectiveness. SUMMARY Naringenin ameliorated the development of ROS formation in hippocamus.Naringenin helped in recovery of antioxidant enzymes.Naringenin decreased seizure severity.Naringenin treatment

17 beta-estradiol but not the phytoestrogen naringenin attenuates aortic cholesterol accumulation in WHHL rabbits

DEFF Research Database (Denmark)

Mortensen, Alicja; Breinholt, V.; Dalsgaard, T.

2001-01-01

The effects of 17 beta -estradiol (17 beta -E-2) or the phytoestrogen naringenin on spontaneous atherosclerosis were studied in 36 ovariectomized homozygous Watanabe heritable hyperlipidemic (WHHL) rabbits receiving a semisynthetic control diet; this diet added 0.0040% 17 beta -E-2, or 0.20% nari...... and its antiatherogenic effect. - Mortensen, A., V. Breinholt, T. Dalsgaard, H. Frandsen, S. T. Lauridsen, J. Laigaard, B. Ottesen, and J-J. Larsen. 17 beta -Estradiol but not the phytoestrogen naringenin attenuates aortic cholesterol accumulation in WHHL rabbits.......The effects of 17 beta -estradiol (17 beta -E-2) or the phytoestrogen naringenin on spontaneous atherosclerosis were studied in 36 ovariectomized homozygous Watanabe heritable hyperlipidemic (WHHL) rabbits receiving a semisynthetic control diet; this diet added 0.0040% 17 beta -E-2, or 0.......20% naringenin, for 16 weeks. The uterine weight was increased (P 17 beta -E-2 group compared with the controls. Total plasma cholesterol and triglycerides were not different from those in the controls, In lipoproteins, HDL...

Protective Effects of Hesperidin (Citrus Flavonone on High Glucose Induced Oxidative Stress and Apoptosis in a Cellular Model for Diabetic Retinopathy

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Wayne Young Liu

2017-12-01

Full Text Available The aim of this study was to investigate the protective effects and mechanisms of hesperidin, a plant based active flavanone found in citrus fruits, under the oxidative stress and apoptosis induced by high levels of glucose in retinal ganglial cells (RGCs. RGC-5 cells were pretreated with hesperidin (12.5, 25, or 50 μmol/L for 6 h followed by exposure to high (33.3 mmol/L d-glucose for 48 h. The 3-(4,5-dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide (MTT assay was adopted to evaluate cell viability. Mitochondrial function was estimated by measuring the mitochondrial membrane potential (ΔΨm. A fluorescent probe was employed to evaluate the intercellular production of reactive oxygen species (ROS. Colorimetric assay kits were used to evaluate lipid peroxidation, antioxidant enzyme activities, and protein carbonyls formation. The expression of apoptosis-related proteins and mitogen-activated protein kinase (MAPK were measured with Western blotting. Hesperidin inhibited high glucose-mediated cell loss and restored mitochondrial function including a reversion of ΔΨm loss and cytochrome c release. Treated with hesperidin, high glucose-induced increase in ROS, malondialdehyde, and protein carbonyl levels were blocked in RGC-5 cells. Hesperidin was found to elevate the activities of superoxide dismutase, catalase, glutathione peroxidase, and to recover glutathione levels. Hesperidin inhibited high glucose-induced cell apoptosis by attenuating the downregulation of caspase-9, caspase-3, and Bax/Bcl-2. Furthermore, the phosphorylation of c-Jun N-terminal kinases (JNK and p38 MAPK triggered by high glucose were attenuated in RGC-5 cells after their incubation with hesperdin. We concluded that hesperidin may protect RGC-5 cells from high glucose-induced injury since it owns the properties of antioxidant action and blocks mitochondria-mediated apoptosis.

Naringenin improves learning and memory in an Alzheimer's disease rat model: Insights into the underlying mechanisms.

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Ghofrani, Saeed; Joghataei, Mohammad-Taghi; Mohseni, Simin; Baluchnejadmojarad, Tourandokht; Bagheri, Maryam; Khamse, Safoura; Roghani, Mehrdad

2015-10-05

Alzheimer's disease (AD) is one of the prevalent neurological disorders of the central nervous system hallmarked by increased beta-amyloid (Aβ) deposition and ensuing learning and memory deficit. In the present study, the beneficial effect of naringenin on improvement of learning and memory was evaluated in an Alzheimer's disease rat model. The Aβ-injected rats showed a lower alternation score in Y-maze task, impairment of retention and recall capability in passive avoidance test, and lower correct choices and higher errors in radial arm maze (RAM) task as compared to sham group in addition to enhanced oxidative stress and apoptosis. Naringenin, but not a combination of naringenin and fulvestrant (an estrogenic receptor antagonist) significantly improved the performance of Aβ-injected rats in passive avoidance and RAM tasks. Naringenin pretreatment of Aβ-injected rats also lowered hippocampal malondialdehyde (MDA) with no significant effect on nitrite and superoxide dismutase (SOD) activity in addition to lowering apoptosis. These results suggest naringenin pretreatment attenuates Aβ-induced impairment of learning and memory through mitigation of lipid peroxidation and apoptosis and its beneficial effect is somewhat mediated via estrogenic pathway. Copyright © 2015 Elsevier B.V. All rights reserved.

Naringenin Regulates Expression of Genes Involved in Cell Wall Synthesis in Herbaspirillum seropedicae▿

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Tadra-Sfeir, M. Z.; Souza, E. M.; Faoro, H.; Müller-Santos, M.; Baura, V. A.; Tuleski, T. R.; Rigo, L. U.; Yates, M. G.; Wassem, R.; Pedrosa, F. O.; Monteiro, R. A.

2011-01-01

Five thousand mutants of Herbaspirillum seropedicae SmR1 carrying random insertions of transposon pTnMod-OGmKmlacZ were screened for differential expression of LacZ in the presence of naringenin. Among the 16 mutants whose expression was regulated by naringenin were genes predicted to be involved in the synthesis of exopolysaccharides, lipopolysaccharides, and auxin. These loci are probably involved in establishing interactions with host plants. PMID:21257805

Naringenin regulates expression of genes involved in cell wall synthesis in Herbaspirillum seropedicae.

Science.gov (United States)

Tadra-Sfeir, M Z; Souza, E M; Faoro, H; Müller-Santos, M; Baura, V A; Tuleski, T R; Rigo, L U; Yates, M G; Wassem, R; Pedrosa, F O; Monteiro, R A

2011-03-01

Five thousand mutants of Herbaspirillum seropedicae SmR1 carrying random insertions of transposon pTnMod-OGmKmlacZ were screened for differential expression of LacZ in the presence of naringenin. Among the 16 mutants whose expression was regulated by naringenin were genes predicted to be involved in the synthesis of exopolysaccharides, lipopolysaccharides, and auxin. These loci are probably involved in establishing interactions with host plants.

Gibbs energies of protonation and complexation of platinum and vanadate metal ions with naringenin and phenolic acids: Theoretical calculations associated with experimental values

International Nuclear Information System (INIS)

Fazary, Ahmed E.; Alshihri, Ayed S.; Alfaifi, Mohammad Y.; Saleh, Kamel A.; Elbehairi, Serag Eldin I.; Fawy, Khaled F.; Abd-Rabboh, Hisham S.M.

2016-01-01

Highlights: • The experimental thermodynamic equilibrium and stability constants of vanadium and platinum complexes involving naringin, ferulic acid, p-coumaric acid, caffeic acid, vanillic acid, sinapic acid, and gallic acid were determined. • The theoretical calculations of the free energy changes associated with the ligand protonation, and metal ion–ligand complex formation equilibria using density function theory calculations, providing a complete picture of the microscopic equilibria of the studied complex systems. - Abstract: The Experimental thermodynamic equilibrium (pK_a values) and stability (log β) constants of vanadium and platinum binary and mixed ligand complexes involving naringenin, ferulic acid, p-coumaric acid, caffeic acid, vanillic acid, sinapic acid, and gallic acid were determined at 310.15 K in 0.16 mol·dm"−"3 KCl aqueous solutions using pH-potentiometric technique and by means of two estimation models (HYPERQUAD 2008 and Bjerrum–Calvin). The theoretical calculations of overall protonation and stability constants of the metal complex species in solution were predicted as the free energy change associated with the ligand protonation, and metal ion–ligand complex formation equilibria (species solvation/de-solvation) using ab initio and density function theory (DFT) calculations. The usage of the experimental potentiometry technique and theoretical predictions provides a complete picture of the microscopic equilibria of the studied systems (vanadium/platinum–naringenin–phenolic acid). Specifically, this theoretically DFT predications would be useful to determine the most real protonation constants of the studied bioligands in which the binding sites changes due to the ligand protonation/deprotonation equilibria. Also, the complexing capacities of vanadium and platinum towards naringenin, ferulic acid, p-coumaric acid, caffeic acid, vanillic acid, sinapic acid, and gallic acid in solutions were evaluated and discussed. From the

Genetic expression profile analysis of the temporal inhibition of quercetin and naringenin on Lactobacillus rhamnosus GG

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The plant polyphenols, quercetin and naringenin, are considered healthy dietary compounds; however, little is known of their effects on the probiotic Lactobacillus rhamnosus GG (LGG). In this study, it was discovered that both quercetin and naringenin produced temporary inhibition of LGG growth, par...

Naringenin protects against 6-OHDA-induced neurotoxicity via activation of the Nrf2/ARE signaling pathway.

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Lou, Haiyan; Jing, Xu; Wei, Xinbing; Shi, Huanying; Ren, Dongmei; Zhang, Xiumei

2014-04-01

There is increasing evidence that oxidative stress is critically involved in the pathogenesis of Parkinson's disease (PD), suggesting that pharmacological targeting of the antioxidant machinery may have therapeutic value. Naringenin, a natural flavonoid compound, has been reported to possess neuroprotective effect against PD related pathology; however the mechanisms underlying its beneficial effects are poorly defined. Thus, the purpose of the present study was to investigate the potential neuroprotective role of naringenin and to delineate its mechanism of action against 6-hydroxydopamine (6-OHDA)-induced neurotoxicity in models of PD both in vitro and in vivo. Naringenin treatment resulted in an increase in nuclear factor E2-related factor 2 (Nrf2) protein levels and subsequent activation of antioxidant response element (ARE) pathway genes in SH-SY5Y cells and in mice. Exposure of SH-SY5Y cells to naringenin provided protection against 6-OHDA-induced oxidative insults that was dependent on Nrf2, since treatment with Nrf2 siRNA failed to block against 6-OHDA neurotoxicity or induce Nrf2-dependent cytoprotective genes in SH-SY5Y cells. In mice, oral administration of naringenin resulted in significant protection against 6-OHDA-induced nigrostriatal dopaminergic neurodegeneration and oxidative damage. Our results indicate that activation of Nrf2/ARE signaling by naringenin is strongly associated with its neuroprotective effects against 6-OHDA neurotoxicity and suggest that targeting the Nrf2/ARE pathway may be a promising approach for therapeutic intervention in PD. Copyright © 2013 Elsevier Ltd. All rights reserved.

Naringenin regulates production of matrix metalloproteinases in the knee-joint and primary cultured articular chondrocytes and alleviates pain in rat osteoarthritis model.

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Wang, C C; Guo, L; Tian, F D; An, N; Luo, L; Hao, R H; Wang, B; Zhou, Z H

2017-03-23

Inflammation of cartilage is a primary symptom for knee-joint osteoarthritis. Matrix metalloproteinases (MMPs) are known to play an important role in the articular cartilage destruction related to osteoarthritis. Naringenin is a plant-derived flavonoid known for its anti-inflammatory properties. We studied the effect of naringenin on the transcriptional expression, secretion and enzymatic activity of MMP-3 in vivo in the murine monosodium iodoacetate (MIA) osteoarthritis model. The assessment of pain behavior was also performed in the MIA rats. The destruction of knee-joint tissues was analyzed microscopically. Moreover, the effect of naringenin was also studied in vitro in IL-1β activated articular chondrocytes. The transcriptional expression of MMP-3, MMP-1, MMP-13, thrombospondin motifs (ADAMTS-4) and ADAMTS-5 was also studied in primary cultured chondrocytes of rats. Naringenin caused significant reduction in pain behavior and showed marked improvement in the tissue morphology of MIA rats. Moreover, a significant inhibition of MMP-3 expression in MIA rats was observed upon treatment with naringenin. In the in vitro tests, naringenin caused a significant reduction in the transcriptional expression, secretion and enzymatic activity of the studied degradative enzymes. The NF-κB pathway was also found to be inhibited upon treatment with naringenin in vitro. Overall, the study suggests that naringenin alleviated pain and regulated the production of matrix-metalloproteinases via regulation of NF-κB pathway. Thus, naringenin could be a potent therapeutic option for the treatment of osteoarthritis.

Naringenin regulates production of matrix metalloproteinases in the knee-joint and primary cultured articular chondrocytes and alleviates pain in rat osteoarthritis model

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C.C. Wang

Full Text Available Inflammation of cartilage is a primary symptom for knee-joint osteoarthritis. Matrix metalloproteinases (MMPs are known to play an important role in the articular cartilage destruction related to osteoarthritis. Naringenin is a plant-derived flavonoid known for its anti-inflammatory properties. We studied the effect of naringenin on the transcriptional expression, secretion and enzymatic activity of MMP-3 in vivo in the murine monosodium iodoacetate (MIA osteoarthritis model. The assessment of pain behavior was also performed in the MIA rats. The destruction of knee-joint tissues was analyzed microscopically. Moreover, the effect of naringenin was also studied in vitro in IL-1β activated articular chondrocytes. The transcriptional expression of MMP-3, MMP-1, MMP-13, thrombospondin motifs (ADAMTS-4 and ADAMTS-5 was also studied in primary cultured chondrocytes of rats. Naringenin caused significant reduction in pain behavior and showed marked improvement in the tissue morphology of MIA rats. Moreover, a significant inhibition of MMP-3 expression in MIA rats was observed upon treatment with naringenin. In the in vitro tests, naringenin caused a significant reduction in the transcriptional expression, secretion and enzymatic activity of the studied degradative enzymes. The NF-κB pathway was also found to be inhibited upon treatment with naringenin in vitro. Overall, the study suggests that naringenin alleviated pain and regulated the production of matrix-metalloproteinases via regulation of NF-κB pathway. Thus, naringenin could be a potent therapeutic option for the treatment of osteoarthritis.

Naringin Improves Neuronal Insulin Signaling, Brain Mitochondrial Function, and Cognitive Function in High-Fat Diet-Induced Obese Mice.

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Wang, Dongmei; Yan, Junqiang; Chen, Jing; Wu, Wenlan; Zhu, Xiaoying; Wang, Yong

2015-10-01

The epidemic and experimental studies have confirmed that the obesity induced by high-fat diet not only caused neuronal insulin resistance, but also induced brain mitochondrial dysfunction as well as learning impairment in mice. Naringin has been reported to posses biological functions which are beneficial to human cognitions, but its protective effects on HFD-induced cognitive deficits and underlying mechanisms have not been well characterized. In the present study Male C57BL/6 J mice were fed either a control or high-fat diet for 20 weeks and then randomized into four groups treated with their respective diets including control diet, control diet + naringin, high-fat diet (HFD), and high-fat diet + naringin (HFDN). The behavioral performance was assessed by using novel object recognition test and Morris water maze test. Hippocampal mitochondrial parameters were analyzed. Then the protein levels of insulin signaling pathway and the AMP-activated protein kinase (AMPK) in the hippocampus were detected by Western blot method. Our results showed that oral administration of naringin significantly improved the learning and memory abilities as evidenced by increasing recognition index by 52.5% in the novel object recognition test and inducing a 1.05-fold increase in the crossing-target number in the probe test, and ameliorated mitochondrial dysfunction in mice caused by HFD consumption. Moreover, naringin significantly enhanced insulin signaling pathway as indicated by a 34.5% increase in the expression levels of IRS-1, a 47.8% decrease in the p-IRS-1, a 1.43-fold increase in the p-Akt, and a 1.89-fold increase in the p-GSK-3β in the hippocampus of the HFDN mice versus HFD mice. Furthermore, the AMPK activity significantly increased in the naringin-treated (100 mg kg(-1) d(-1)) group. These findings suggest that an enhancement in insulin signaling and a decrease in mitochondrial dysfunction through the activation of AMPK may be one of the mechanisms that naringin

Induction of apoptosis and antiproliferative activity of naringenin in human epidermoid carcinoma cell through ROS generation and cell cycle arrest.

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Md Sultan Ahamad

Full Text Available A natural predominant flavanone naringenin, especially abundant in citrus fruits, has a wide range of pharmacological activities. The search for antiproliferative agents that reduce skin carcinoma is a task of great importance. The objective of this study was to analyze the anti-proliferative and apoptotic mechanism of naringenin using MTT assay, DNA fragmentation, nuclear condensation, change in mitochondrial membrane potential, cell cycle kinetics and caspase-3 as biomarkers and to investigate the ability to induce reactive oxygen species (ROS initiating apoptotic cascade in human epidermoid carcinoma A431 cells. Results showed that naringenin exposure significantly reduced the cell viability of A431 cells (p<0.01 with a concomitant increase in nuclear condensation and DNA fragmentation in a dose dependent manner. The intracellular ROS generation assay showed statistically significant (p<0.001 dose-related increment in ROS production for naringenin. It also caused naringenin-mediated epidermoid carcinoma apoptosis by inducing mitochondrial depolarization. Cell cycle study showed that naringenin induced cell cycle arrest in G0/G1 phase of cell cycle and caspase-3 analysis revealed a dose dependent increment in caspase-3 activity which led to cell apoptosis. This study confirms the efficacy of naringenin that lead to cell death in epidermoid carcinoma cells via inducing ROS generation, mitochondrial depolarization, nuclear condensation, DNA fragmentation, cell cycle arrest in G0/G1 phase and caspase-3 activation.

Naringenin modulates the metastasis of human prostate cancer cells by down regulating the matrix metalloproteinases -2/-9 via ROS/ERK1/2 pathways

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Er-Jiang Lin

2014-08-01

Full Text Available Metastasis is a multifactorial condition that complicates cancer treatment options and widens the target of treatment. Matrix mettalopriteinases (MMPs of the extracellular matrix (ECM are involved in metastasis, thus they present as potential targets in halting cancer metastasis. The study was undertaken to investigate the influence of naringenin, a naturally occurring flavonoid on the metastasis of human prostate cancer cells (PC-3 and DU145. Naringenin was observed to be effective in reducing the viability and migratory percentage of PC-3 and DU145 cells. Naringenin significantly reduced the expression and activities of the chief MMPs (MMP-2 and MMP-9 as assessed by western blotting, real-time PCR and gelatin zymography analysis. The influence of naringenin on extracellular signal-regulated kinase (ERK -ERK1/2 was analysed by western blotting. The results indicated that naringenin was able to effectively inhibit ERK1/2. Naringenin exposure also significantly suppressed the levels of reactive oxygen species (ROS. Naringenin thus stands as an effective chemotherapeutic agent for prostate cancer treatment that could be further explored.

The beneficial role of Naringin- a citrus bioflavonoid, against oxidative stress-induced neurobehavioral disorders and cognitive dysfunction in rodents: A systematic review and meta-analysis.

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Viswanatha, Gollapalle Lakshminarayanashastry; Shylaja, H; Moolemath, Yogananda

2017-10-01

Naringin is a bioflavonoid, very abundantly found in citrus species. In literature, naringin has been scientifically well documented for its beneficial effects in various neurological disorders. In this systematic review and meta-analysis, we have made an attempt to correlate the protective role of naringin against oxidative stress-induced neurological disorders in rodents. The systematic search was performed using electronic databases; the search was mainly focused on the role of naringin in oxidative stress-induced neuropathological conditions in rodents. While, the meta-analysis was performed on the effect of naringin on oxidative stress markers [superoxide dismutase (SOD), catalase (CAT), glutathione-S-transferase (GST), reduced glutathione (GSH), lipid peroxidation (LPO)], nitrite, mitochondrial complexes (I to IV) and enzymes (acetylcholinesterase, Na + -K + -ATPase, Ca 2+ -ATPase, and Mg 2+ -ATPase) in the rodent brain. The data was analyzed using Review Manager Software. Based on the inclusion and exclusion criteria, twenty studies were selected. The meta-analysis revealed that, naringin could significantly inhibit various physical and chemical stimuli- induced neurological perturbances in the rodent brain, mediated through oxidative stress. Further, naringin also significantly restored the levels of all the oxidative stress markers (oxidative, nitrosative, enzymes, and mitochondrial complexes) in different parts of the rodent brain. This systematic review and meta-analysis supports the available scientific evidence on the beneficial role of naringin in the management of various neurological ailments. However, further studies involving human subjects is recommended to establish the safety and therapeutic efficacy in humans. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Phytochemical Contents of Five Artemisia Species

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Murat KURSAT

2015-12-01

Full Text Available In the present study, the fatty acid compositions, vitamin, sterol contents and flavonoid constituents of five Turkish Artemisia species (A. armeniaca, A. incana , A. tournefortiana, A. haussknechtii and A. scoparia were determined by GC and HPLC techniques. The results of the fatty acid analysis showed that Artemisia species possess high saturated fatty acid compositions. On the other hand, the studied Artemisia species were found to have low vitamin and sterol contents. Eight flavononids (catechin, naringin, rutin, myricetin, morin, naringenin, quercetin, kaempferol were determined in the present study. It was found that Artemisia species contained high levels of flavonoids. Morin (45.35 ± 0.65 – 1406.79 ± 4.12 μg/g and naringenin (15.32 ± 0.46 – 191.18 ± 1.22 μg/g were identified in all five species. Naringin (268.13 ± 1.52 – 226.43 ± 1.17 μg/g and kaempferol (21.74 ± 0.65 – 262.19 ± 1.38 μg/g contents were noted in the present study. Present research showed that the studied Artemisia taxa have high saturated fatty acids and also rich flavonoid content.

Citrus Polyphenol Hesperidin Stimulates Production of Nitric Oxide in Endothelial Cells while Improving Endothelial Function and Reducing Inflammatory Markers in Patients with Metabolic Syndrome

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Rizza, Stefano; Muniyappa, Ranganath; Iantorno, Micaela; Kim, Jeong-a; Chen, Hui; Pullikotil, Philomena; Senese, Nicoletta; Tesauro, Manfredi; Lauro, Davide; Cardillo, Carmine

2011-01-01

Context: Hesperidin, a citrus flavonoid, and its metabolite hesperetin may have vascular actions relevant to their health benefits. Molecular and physiological mechanisms of hesperetin actions are unknown. Objective: We tested whether hesperetin stimulates production of nitric oxide (NO) from vascular endothelium and evaluated endothelial function in subjects with metabolic syndrome on oral hesperidin therapy. Design, Setting, and Interventions: Cellular mechanisms of action of hesperetin were evaluated in bovine aortic endothelial cells (BAEC) in primary culture. A randomized, placebo-controlled, double-blind, crossover trial examined whether oral hesperidin administration (500 mg once daily for 3 wk) improves endothelial function in individuals with metabolic syndrome (n = 24). Main Outcome Measure: We measured the difference in brachial artery flow-mediated dilation between placebo and hesperidin treatment periods. Results: Treatment of BAEC with hesperetin acutely stimulated phosphorylation of Src, Akt, AMP kinase, and endothelial NO synthase to produce NO; this required generation of H2O2. Increased adhesion of monocytes to BAEC and expression of vascular cell adhesion molecule-1 in response to TNF-α treatment was reduced by pretreatment with hesperetin. In the clinical study, when compared with placebo, hesperidin treatment increased flow-mediated dilation (10.26 ± 1.19 vs. 7.78 ± 0.76%; P = 0.02) and reduced concentrations of circulating inflammatory biomarkers (high-sensitivity C-reactive protein, serum amyloid A protein, soluble E-selectin). Conclusions: Novel mechanisms for hesperetin action in endothelial cells inform effects of oral hesperidin treatment to improve endothelial dysfunction and reduce circulating markers of inflammation in our exploratory clinical trial. Hesperetin has vasculoprotective actions that may explain beneficial cardiovascular effects of citrus consumption. PMID:21346065

NMR Characterization of Flavanone Naringenin 7-O-Glycoside Diastereomer

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SUN Li-juan

2017-12-01

Full Text Available To discriminate R and S flavanone glycoside using NMR, the mixture of R and S naringenin 7-O-glycoside was first isolated from Gleditsia sinensis. 1H and 13C NMR data of the mixture were recorded with 1H NMR, 13C NMR, 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC in DMSO-d6 solution. The two diastereomers were then separated with chiral chromatographic isolation, with their absolute configurations determined by circular dichroism. To avoid the disturbance of protons from glucose residues to dihydroflavonoid, 1H NMR spectra were acquired for pure R and S naringenin 7-O-glycoside and their mixture in CD3CN. The two diastereomers showed the largest proton chemical shift differences at the end group of glucose residue (H-1" with a chemical shift difference of 9.4 Hz. The OH-5 proton showed a chemical shift difference of 5.8 Hz. The chemical shift of the three protons on ring C were all influenced by configuration.

Rapid Quantitation of Furanocoumarins and Flavonoids in Grapefruit Juice using Ultra-Performance Liquid Chromatography.

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Vandermolen, Karen M; Cech, Nadja B; Paine, Mary F; Oberlies, Nicholas H

2013-01-01

Grapefruit juice can increase or decrease the systemic exposure of myriad oral medications, leading to untoward effects or reduced efficacy. Furanocoumarins in grapefruit juice have been established as inhibitors of cytochrome P450 3A (CYP3A)-mediated metabolism and P-glycoprotein (P-gp)-mediated efflux, while flavonoids have been implicated as inhibitors of organic anion transporting polypeptide (OATP)-mediated absorptive uptake in the intestine. The potential for drug interactions with a food product necessitates an understanding of the expected concentrations of a suite of structurally diverse and potentially bioactive compounds. Develop methods for the rapid quantitation of two furanocoumarins (bergamottin and 6',7'-dihydroxybergamottin) and four flavonoids (naringin, naringenin, narirutin and hesperidin) in five grapefruit juice products using ultra-performance liquid chromatography (UPLC). Grapefruit juice products were extracted with ethyl acetate; the concentrated extract was analysed by UPLC using acetonitrile:water gradients and a C18 -column. Analytes were detected using a photodiode array detector, set at 250 nm (furanocoumarins) and 310 nm (flavonoids). Intraday and interday precision and accuracy and limits of detection and quantitation were determined. Rapid (0.999. Considerable between-juice variation in the concentrations of these compounds was observed, and the quantities measured were in agreement with the concentrations published in HPLC studies. These analytical methods provide an expedient means to quantitate key furanocoumarins and flavonoids in grapefruit juice and other foods used in dietary substance-drug interaction studies. Copyright © 2013 John Wiley & Sons, Ltd.

Insulin Sensitizing and Antioxidant Effects of Hesperidin and Low Dose Gamma Irradiation in Combination with Rosiglitazone in Type 2 Diabetic Rats

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Morcos, N.Y.; Abdel-Ghaffar, A.B.; Osman, S.A.; Mohamed, M.Kh.; Arbid, M.S.; El-Eraky, W.I.

2012-01-01

The present study was designed to investigate the possible ameliorative effect of hesperidin and low dose fÁ-irradiation (LDR) in combination with rosiglitazone in an experimental model of insulin resistance. Type 2 diabetes mellitus (T2DM) was induced in rats by single intraperitoneal injection of streptozotocin (STZ) followed by nicotinamide (NIC) (65 and 110 mg/kg b.wt; i.p respectively). After verifying T2DM in rats, they were subjected to LDR (50 cGy) and then treated with rosiglitazone (4 mg/kg b.wt; p.o) and hesperidin (100 mg/kg b.wt; p.o) for 30 days. Results showed that STZ injection significantly elevated blood glucose, glycosylated hemoglobin (HbA1c), insulin, homeostasis model assessment of insulin resistance (HOMA-IR), lipid peroxides (TBARS; MDA) accompanied with a reduction in adiponectin plasma level, reduced glutathione (GSH) and superoxide dismutase (SOD) serum level. Treatment of diabetic rats with rosiglitazone, hesperidin and LDR significantly reduced blood glucose, HbA1c, insulin, HOMA-IR and MDA levels. Whereas, plasma adiponectin, SOD in serum and GSH plasma level were significantly elevated. Therefore, our data suggest that hesperidin and LDR might be useful adjuvants with rosiglitazone and attenuate insulin resistance and oxidative stress in T2DM.

77 FR 40076 - Prospective Grant of Exclusive License: Use of the Citrus Flavanones Hesperetin, Hesperidin, and...

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2012-07-06

.... Investigators from the National Center for Complementary and Alternative Medicine have demonstrated that... controls. Thus, hesperidin and its active aglycone form, hesperetin, may be effective agents for the...

The dietary flavonoids naringenin and quercetin acutely impair glucose metabolism in rodents possibly via inhibition of hypothalamic insulin signalling.

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Koch, Christiane E; Ganjam, Goutham K; Steger, Juliane; Legler, Karen; Stöhr, Sigrid; Schumacher, Daniela; Hoggard, Nigel; Heldmaier, Gerhard; Tups, Alexander

2013-03-28

Secondary metabolites of herbs and spices are widely used as an alternative strategy in the therapy of various diseases. The polyphenols naringenin, quercetin and curcumin have been characterised as anti-diabetic agents. Conversely, in vitro, naringenin and quercetin are described to inhibit phosphoinositide-3-kinase (PI3K), an enzyme that is essential for the neuronal control of whole body glucose homoeostasis. Using both in vitro and in vivo experiments, we tested whether the inhibitory effect on PI3K occurs in neurons and if it might affect whole body glucose homoeostasis. Quercetin was found to inhibit basal and insulin-induced phosphorylation of Akt (Ser473), a downstream target of PI3K, in HT-22 cells, whereas naringenin and curcumin had no effect. In Djungarian hamsters (Phodopus sungorus) naringenin and quercetin (10 mg/kg administered orally) diminished insulin-induced phosphorylation of Akt (Ser473) in the arcuate nucleus, indicating a reduction in hypothalamic PI3K activity. In agreement with this finding, glucose tolerance in naringenin-treated hamsters (oral) and mice (oral and intracerebroventricular) was reduced compared with controls. Dietary quercetin also impaired glucose tolerance, whereas curcumin was ineffective. Circulating levels of insulin and insulin-like growth factor-binding protein were not affected by the polyphenols. Oral quercetin reduced the respiratory quotient, suggesting that glucose utilisation was impaired after treatment. These data demonstrate that low doses of naringenin and quercetin acutely and potently impair glucose homoeostasis. This effect may be mediated by inhibition of hypothalamic PI3K signalling. Whether chronic impairments in glucose homoeostasis occur after long-term application remains to be identified.

Solidification of hesperidin nanosuspension by spray drying optimized by design of experiment (DoE).

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Wei, Qionghua; Keck, Cornelia M; Müller, Rainer H

2018-01-01

To accelerate the determination of optimal spray drying parameters, a "Design of Experiment" (DoE) software was applied to produce well redispersible hesperidin nanocrystals. For final solid dosage forms, aqueous liquid nanosuspensions need to be solidified, whereas spray drying is a large-scale cost-effective industrial process. A nanosuspension with 18% (w/w) of hesperidin stabilized by 1% (w/w) of poloxamer 188 was produced by wet bead milling. The sizes of original and redispersed spray-dried nanosuspensions were determined by laser diffractometry (LD) and photon correlation spectroscopy (PCS) and used as effect parameters. In addition, light microscopy was performed to judge the redispersion quality. After a two-step design of MODDE 9, screening model and response surface model (RSM), the inlet temperature of spray dryer and the concentration of protectant (polyvinylpyrrolidone, PVP K25) were identified as the most important factors affecting the redispersion of nanocrystals. As predicted in the RSM modeling, when 5% (w/w) of PVP K25 was added in an 18% (w/w) of hesperidin nanosuspension, subsequently spray-dried at an inlet temperature of 100 °C, well redispersed solid nanocrystals with an average particle size of 276 nm were obtained. By the use of PVP K25, the saturation solubility of the redispersed nanocrystals in water was improved to 86.81 µg/ml, about 2.5-fold of the original nanosuspension. In addition, the dissolution velocity was accelerated. This was attributed to the additional effects of steric stabilization on the nanocrystals and solubilization by the PVP polymer from spray drying.

Naringenin inhibits the growth and stimulates the lignification of soybean root

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Graciene de Souza Bido

2010-06-01

Full Text Available The flavanone naringenin, an intermediate in flavonoid biosynthesis, was tested for its effect on root growth, phenylalanine ammonia-lyase (PAL and peroxidase (POD activities, as well as phenolic compounds and lignin contents in soybean (Glycine max L. Merrill seedlings. Three-day-old seedlings were cultivated in half-strength Hoagland nutrient solution (pH 6.0, with or without 0.1 to 0.4 mM naringenin in a growth chamber (25°C, 12-h photoperiod, irradiance of 280 µmol m-2 s-1 for 24 h. Inhibitory effects on root growth (length, weight, cell viability, PAL and soluble POD activities were detected after naringenin treatments. These effects were associated with stimulatory activity of the cell wall-bound POD followed by an increase in the lignin contents, suggesting that naringenin-induced inhibition in soybean roots could be due to the lignification process.Os efeitos de naringenina, um intermediário da biossíntese de flavonóides, foram avaliados sobre o crescimento das raízes, as atividades da fenilalanina amônia liase (PAL e peroxidases, bem como sobre os teores de compostos fenólicos e de lignina em plântulas de soja (Glycine max L. Merrill. Plântulas de três dias foram cultivadas em solução nutritiva de Hoagland, meia-força (pH 6,0, contendo ou não, naringenina 0,1 a 0,4 mM, em uma câmara de germinação (25°C, fotoperíodo de 12 h, 280 µmol m-2 s-1 durante 24 h. Efeitos inibitórios no crescimento das raízes (comprimento, massa e viabilidade celular e nas atividades da PAL e POD solúvel foram constatados após os tratamentos com naringenina. Estes efeitos foram associados com atividade estimulatória da POD ligada à parede celular, seguido por aumento nos teores de lignina, sugerindo que a inibição do crescimento das raízes pode ser devido ao processo de lignificação.

Modular optimization of heterologous pathways for de novo synthesis of (2S-naringenin in Escherichia coli.

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Junjun Wu

Full Text Available Due to increasing concerns about food safety and environmental issues, bio-based production of flavonoids from safe, inexpensive, and renewable substrates is increasingly attracting attention. Here, the complete biosynthetic pathway, consisting of 3-deoxy-D-arabinoheptulosonate 7-phosphate synthase (DAHPS, chorismate mutase/prephenate dehydrogenase (CM/PDH, tyrosine ammonia lyase (TAL, 4-coumarate:CoA ligase (4CL, chalcone synthase (CHS, chalcone isomerase (CHI, malonate synthetase, and malonate carrier protein, was constructed using pre-made modules to overproduce (2S-naringenin from D-glucose. Modular pathway engineering strategies were applied to the production of the flavonoid precursor (2S-naringenin from L-tyrosine to investigate the metabolic space for efficient conversion. Modular expression was combinatorially tuned by modifying plasmid gene copy numbers and promoter strengths to identify an optimally balanced pathway. Furthermore, a new modular pathway from D-glucose to L-tyrosine was assembled and re-optimized with the identified optimal modules to enable de novo synthesis of (2S-naringenin. Once this metabolic balance was achieved, the optimum strain was capable of producing 100.64 mg/L (2S-naringenin directly from D-glucose, which is the highest production titer from D-glucose in Escherichia coli. The fermentation system described here paves the way for the development of an economical process for microbial production of flavonoids.

Changes in flavonoid content of grapefruit juice caused by thermal treatment and storage

OpenAIRE

Igual Ramo, Marta; García Martínez, Eva María; Camacho Vidal, Mª Mar; Martínez Navarrete, Nuria

2011-01-01

The effect of conventional and microwave pasteurization on the main flavonoids present in grapefruit juice and their stability throughout 2 months of refrigerated and frozen storage was evaluated. Individual flavonoids were analyzed by HPLC. The results showed that naringin, narirutin, quercetin and naringenin were the most abundant flavonoids in grapefruit juice. In general, although every pasteurization treatment caused a significant reduction in the content of all the studied flavonoids, t...

Comparative evaluation of 12 immature citrus fruit extracts for the inhibition of cytochrome P450 isoform activities.

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Fujita, Tadashi; Kawase, Atsushi; Niwa, Toshiro; Tomohiro, Norimichi; Masuda, Megumi; Matsuda, Hideaki; Iwaki, Masahiro

2008-05-01

In a previous study we found that 50% ethanol extracts of immature fruits of Citrus unshiu (satsuma mandarin) have anti-allergic effects against the Type I, II and IV allergic reactions. However, many adverse interactions between citrus fruit, especially grapefruit juice, and drugs have been reported due to the inhibition of cytochrome P450 (CYP) activities. The purpose of this study was to examine the competitive inhibitory effects of extracts from immature citrus fruit on CYP activity. Extracts were prepared from 12 citrus species or cultivars, and were tested against three kinds of major CYPs, CYP2C9, CYP2D6 and CYP3A4, in human liver microsomes. We also estimated the amounts of flavonoids (narirutin, hesperidin, naringin and neohesperidin) and furanocoumarins (bergapten, 6',7'-dihydroxybergamottin and bergamottin) in each extract using HPLC. Citrus paradisi (grapefruit) showed the greatest inhibition of CYP activities, while Citrus unshiu which has an antiallergic effect, showed relatively weak inhibitory effects. Extracts having relatively strong inhibitory effects for CYP3A4 tended to contain higher amounts of naringin, bergamottin and 6',7'-dihydroxybergamottin. These results, providing comparative information on the inhibitory effects of citrus extracts on CYP isoforms, suggest that citrus extracts containing high levels of narirutin and hesperidin and lower levels of furanocoumarins such as C. unshiu are favorable as antiallergic functional ingredients.

Covalent attachment of the plant natural product naringenin to small glass and ceramic beads

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Grotewold Erich

2005-10-01

Full Text Available Abstract Background Natural products have numerous medicinal applications and play important roles in the biology of the organisms that accumulate them. Few methods are currently available for identifying proteins that bind to small molecules, therefore the discovery of cellular targets for natural products with pharmacological activity continues to pose a significant challenge in drug validation. Similarly, the identification of enzymes that participate in the biosynthesis or modification of natural products remains a formidable bottleneck for metabolic engineering. Flavonoids are one large group of natural products with a diverse number of functions in plants and in human health. The coupling of flavonoids to small ceramic and glass beads provides a first step in the development of high-throughput, solid-support base approaches to screen complex libraries to identify proteins that bind natural products. Results The utilization of small glass and ceramic beads as solid supports for the coupling of small molecules was explored. Initial characterization of the beads indicated uniform and high capacity loading of amino groups. Once the beads were deemed adequate for the linking of small molecules by the coupling of NHS-fluorescein followed by microscopy, chemical hydrolysis and fluorometry, the flavonoid naringenin was modified with 1,4-dibromobutane, followed by the attachment of aminopropyltriethoxysilane. After NMR structural confirmation, the resulting 7-(4-(3-(triethoxysilylpropylaminobutoxy naringenin was attached to the ceramic beads. Conclusion Our results demonstrate that ceramic and glass beads provide convenient solid supports for the efficient and facile coupling of small molecules. We succeeded in generating naringenin-coupled ceramic and glass beads. We also developed a convenient series of steps that can be applied for the solid-support coupling of other related flavonoids. The availability of solid-support coupled naringenin opens

Neuroprotective Effects of Hesperidin, a Plant Flavanone, on Rotenone-Induced Oxidative Stress and Apoptosis in a Cellular Model for Parkinson’s Disease

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Kuppusamy Tamilselvam

2013-01-01

Full Text Available Rotenone a widely used pesticide that inhibits mitochondrial complex I has been used to investigate the pathobiology of PD both in vitro and in vivo. Studies have shown that the neurotoxicity of rotenone may be related to its ability to generate reactive oxygen species (ROS, leading to neuronal apoptosis. The current study was carried out to investigate the neuroprotective effects of hesperidin, a citrus fruit flavanol, against rotenone-induced apoptosis in human neuroblastoma SK-N-SH cells. We assessed cell death, mitochondrial membrane potential, ROS generation, ATP levels, thiobarbituric acid reactive substances, reduced glutathione (GSH levels, and the activity of catalase, superoxide dismutase (SOD and glutathione peroxidase (GPx using well established assays. Apoptosis was determined in normal, rotenone, and hesperidin treated cells, by measuring the protein expression of cytochrome c (cyt c, caspases 3 and 9, Bax, and Bcl-2 using the standard western blotting technique. The apoptosis in rotenone-induced SK-N-SH cells was accompanied by the loss of mitochondrial membrane potential, increased ROS generation, the depletion of GSH, enhanced activities of enzymatic antioxidants, upregulation of Bax, cyt c, and caspases 3 and 9, and downregulation of Bcl-2, which were attenuated in the presence of hesperidin. Our data suggests that hesperidin exerts its neuroprotective effect against rotenone due to its antioxidant, maintenance of mitochondrial function, and antiapoptotic properties in a neuroblastoma cell line.

Naringin Reverses Hepatocyte Apoptosis and Oxidative Stress Associated with HIV-1 Nucleotide Reverse Transcriptase Inhibitors-Induced Metabolic Complications

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Oluwafeyisetan O. Adebiyi

2015-12-01

Full Text Available Nucleoside Reverse Transcriptase Inhibitors (NRTIs have not only improved therapeutic outcomes in the treatment of HIV infection but have also led to an increase in associated metabolic complications of NRTIs. Naringin’s effects in mitigating NRTI-induced complications were investigated in this study. Wistar rats, randomly allotted into seven groups (n = 7 were orally treated daily for 56 days with 100 mg/kg zidovudine (AZT (groups I, II III, 50 mg/kg stavudine (d4T (groups IV, V, VI and 3 mL/kg of distilled water (group VII. Additionally, rats in groups II and V were similarly treated with 50 mg/kg naringin, while groups III and VI were treated with 45 mg/kg vitamin E. AZT or d4T treatment significantly reduced body weight and plasma high density lipoprotein concentrations but increased liver weights, plasma triglycerides and total cholesterol compared to controls, respectively. Furthermore, AZT or d4T treatment significantly increased oxidative stress, adiposity index and expression of Bax protein, but reduced Bcl-2 protein expression compared to controls, respectively. However, either naringin or vitamin E significantly mitigated AZT- or d4T-induced weight loss, dyslipidemia, oxidative stress and hepatocyte apoptosis compared to AZT- or d4T-only treated rats. Our results suggest that naringin reverses metabolic complications associated with NRTIs by ameliorating oxidative stress and apoptosis. This implies that naringin supplements could mitigate lipodystrophy and dyslipidemia associated with NRTI therapy.

Genetic and functional characterization of a novel meta-pathway for degradation of naringenin in Herbaspirillum seropedicae SmR1.

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Maria Marin, Anelis; de la Torre, Jésus; Ricardo Marques Oliveira, Alfredo; Barison, Andersson; Satie Chubatsu, Leda; Adele Monteiro, Rose; de Oliveira Pedrosa, Fabio; Maltempi de Souza, Emanuel; Wassem, Roseli; Duque, Estrella; Ramos, Juan-Luis

2016-12-01

In this study, a random mutant library of Herbaspirillum seropedicae SmR1 was constructed by Tn5 insertion and a mutant incapable of utilizing naringenin as a carbon source was isolated. The Tn5 transposon was found to be inserted in the fdeE gene (Hsero_1007), which encodes a monooxygenase. Two other mutant strains in fdeC (Hsero_1005) and fdeG (Hsero_1009) genes coding for a dioxygenase and a putative cyclase, respectively, were obtained by site-directed mutagenesis and then characterized. Liquid Chromatography coupled to mass spectrometry (LC-MS)/MS analyses of culture supernatant from the fdeE mutant strain revealed that naringenin remained unaltered, suggesting that the FdeE protein is involved in the initial step of naringenin degradation. LC-MS/MS analyses of culture supernatants from the wild-type (SmR1) and FdeC deficient mutant suggested that in H. seropedicae SmR1 naringenin is first mono-oxygenated by the FdeE protein, to produce 5,7,8-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one, that is subsequently dioxygenated and cleaved at the A-ring by the FdeC dioxygenase, since the latter compound accumulated in the fdeC strain. After meta-cleavage of the A-ring, the subsequent metabolic steps generate oxaloacetic acid that is metabolized via the tricarboxylic acid cycle. This bacterium can also modify naringenin by attaching a glycosyl group to the B-ring or a methoxy group to the A-ring, leading to the generation of dead-end products. © 2016 Society for Applied Microbiology and John Wiley & Sons Ltd.

Transcriptional regulation of human and rat hepatic lipid metabolism by the grapefruit flavonoid naringenin: role of PPARalpha, PPARgamma and LXRalpha.

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Jonathan Goldwasser

2010-08-01

Full Text Available Disruption of lipid and carbohydrate homeostasis is an important factor in the development of prevalent metabolic diseases such as diabetes, obesity, and atherosclerosis. Therefore, small molecules that could reduce insulin dependence and regulate dyslipidemia could have a dramatic effect on public health. The grapefruit flavonoid naringenin has been shown to normalize lipids in diabetes and hypercholesterolemia, as well as inhibit the production of HCV. Here, we demonstrate that naringenin regulates the activity of nuclear receptors PPARalpha, PPARgamma, and LXRalpha. We show it activates the ligand-binding domain of both PPARalpha and PPARgamma, while inhibiting LXRalpha in GAL4-fusion reporters. Using TR-FRET, we show that naringenin is a partial agonist of LXRalpha, inhibiting its association with Trap220 co-activator in the presence of TO901317. In addition, naringenin induces the expression of PPARalpha co-activator, PGC1alpha. The flavonoid activates PPAR response element (PPRE while suppressing LXRalpha response element (LXRE in human hepatocytes, translating into the induction of PPAR-regulated fatty acid oxidation genes such as CYP4A11, ACOX, UCP1 and ApoAI, and inhibition of LXRalpha-regulated lipogenesis genes, such as FAS, ABCA1, ABCG1, and HMGR. This effect results in the induction of a fasted-like state in primary rat hepatocytes in which fatty acid oxidation increases, while cholesterol and bile acid production decreases. Our findings explain the myriad effects of naringenin and support its continued clinical development. Of note, this is the first description of a non-toxic, naturally occurring LXRalpha inhibitor.

Rapid Quantitation of Furanocoumarins and Flavonoids in Grapefruit Juice using Ultra Performance Liquid Chromatography

Science.gov (United States)

VanderMolen, Karen M.; Cech, Nadja B.; Paine, Mary F.

2013-01-01

Introduction Grapefruit juice can increase or decrease the systemic exposure of myriad oral medications, leading to untoward effects or reduced efficacy. Furanocoumarins in grapefruit juice have been established as inhibitors of cytochrome P450 3A (CYP3A)-mediated metabolism and P-glycoprotein (P-gp)-mediated efflux, while flavonoids have been implicated as inhibitors of organic anion transporting polypeptide (OATP)-mediated absorptive uptake in the intestine. The potential for drug interactions with a food product necessitates an understanding of the expected concentrations of a suite of structurally diverse and potentially bioactive compounds. Objective Develop methods for the rapid quantitation of two furanocoumarins (bergamottin and 6′,7′-dihydroxybergamottin) and four flavonoids (naringin, naringenin, narirutin, and hesperidin) in five grapefruit juice products using ultra performance liquid chromatography (UPLC). Methodology Grapefruit juice products were extracted with ethyl acetate; the concentrated extract was analyzed by UPLC using acetonitrile:water gradients and a C18 column. Analytes were detected using a photodiode array detector, set at 250 nm (furanocoumarins) and 310 nm (flavonoids). Intraday and interday precision and accuracy and limits of detection and quantitation were determined. Results Rapid (flavonoids. R2 values for the calibration curves of all analytes were >0.999. Considerable between-juice variation in the concentrations of these compounds was observed, and the quantities measured were in agreement with the concentrations published in HPLC studies. Conclusion These analytical methods provide an expedient means to quantitate key furanocoumarins and flavonoids in grapefruit juice and other foods used in dietary substance-drug interaction studies. PMID:23780830

Quantification and localization of hesperidin and rutin in Citrus sinensis grafted on C. limonia after Xylella fastidiosa infection by HPLC-UV and MALDI imaging mass spectrometry.

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Soares, Márcio Santos; da Silva, Danielle Fernandes; Forim, Moacir Rossi; da Silva, Maria Fátima das Graças Fernandes; Fernandes, João Batista; Vieira, Paulo Cezar; Silva, Denise Brentan; Lopes, Norberto Peporine; de Carvalho, Sérgio Alves; de Souza, Alessandra Alves; Machado, Marcos Antônio

2015-07-01

A high performance liquid chromatography-ultraviolet (HPLC-UV) method was developed for quantifying hesperidin and rutin levels in leaves and stems of Citrus limonia, with a good linearity over a range of 1.0-80.0 and 1.0-50.0 μg mL(-1) respectively, with r(2)>0.999 for all curves. The limits of detection (LOD) for both flavonoids were 0.6 and 0.5 μg mL(-1), respectively, with quantification (LOQ) being 2.0 and 1.0 μg mL(-1), respectively. The quantification method was applied to Citrus sinensis grafted onto C. limonia with and without CVC (citrus variegated chlorosis) symptoms after Xylella fastidiosa infection. The total content of rutin was low and practically constant in all analyses in comparison with hesperidin, which showed a significant increase in its amount in symptomatic leaves. Scanning electron microscopy studies on leaves with CVC symptoms showed vessel occlusion by biofilm, and a crystallized material was noted. Considering the difficulty in isolating these crystals for analysis, tissue sections were analyzed by matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI MSI) to confirm the presence of hesperidin at the site of infection. The images constructed from MS/MS data with a specific diagnostic fragment ion (m/z 483) also showed higher ion intensities for it in infected plants than in healthy ones, mainly in the vessel regions. These data suggest that hesperidin plays a role in the plant-pathogen interaction, probably as a phytoanticipin. This method was also applied to C. sinensis and C. limonia seedlings, and comparison with the graft results showed that the rootstock had an increased hesperidin content ∼3.6 fold greater in the graft stem than in the stem of C. sinensis seedlings. Increase in hesperidin content by rootstock can be related to induced internal defense mechanisms. Copyright © 2015 Elsevier Ltd. All rights reserved.

Naringenin-responsive riboswitch-based fluorescent biosensor module for Escherichia coli co-cultures.

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Xiu, Yu; Jang, Sungho; Jones, J Andrew; Zill, Nicholas A; Linhardt, Robert J; Yuan, Qipeng; Jung, Gyoo Yeol; Koffas, Mattheos A G

2017-10-01

The ability to design and construct combinatorial synthetic metabolic pathways has far exceeded our capacity for efficient screening and selection of the resulting microbial strains. The need for high-throughput rapid screening techniques is of upmost importance for the future of synthetic biology and metabolic engineering. Here we describe the development of an RNA riboswitch-based biosensor module with dual fluorescent reporters, and demonstrate a high-throughput flow cytometry-based screening method for identification of naringenin over producing Escherichia coli strains in co-culture. Our efforts helped identify a number of key operating parameters that affect biosensor performance, including the selection of promoter and linker elements within the sensor-actuator domain, and the effect of host strain, fermentation time, and growth medium on sensor dynamic range. The resulting biosensor demonstrates a high correlation between specific fluorescence of the biosensor strain and naringenin titer produced by the second member of the synthetic co-culture system. This technique represents a novel application for synthetic microbial co-cultures and can be expanded from naringenin to any metabolite if a suitable riboswitch is identified. The co-culture technique presented here can be applied to a variety of target metabolites in combination with the SELEX approach for aptamer design. Due to the compartmentalization of the two genetic constructs responsible for production and detection into separate cells and application as independent modules of a synthetic microbial co-culture we have subsequently reduced the need for re-optimization of the producer module when the biosensor is replaced or removed. Biotechnol. Bioeng. 2017;114: 2235-2244. © 2017 Wiley Periodicals, Inc. © 2017 Wiley Periodicals, Inc.

Relative bioavailability of the flavonoids quercetin, hesperetin and naringenin given simultaneously through diet

DEFF Research Database (Denmark)

Krogholm, Kirstine Suszkiewicz; Bredsdorff, Lea; Knuthsen, Pia

2010-01-01

.5 +/- 1%) compared with hesperetin (14.2 +/- 9.1%) and naringenin (22.6 +/- 11.5%) and shows that this is not due to a lower bioavailability of quercetin, but rather reflects different clearance mechanisms. European Journal of Clinical Nutrition (2010) 64, 432-435; doi: 10.1038/ejcn.2010.6; published...

Rapid Quantitative Analysis of Naringenin in the Fruit Bodies of Inonotus vaninii by Two-phase Acid Hydrolysis Followed by Reversed Phase-high Performance Liquid Chromatography-ultra Violet.

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Guohua, Xia; Pan, Ruirong; Bao, Rui; Ge, Yanru; Zhou, Cunshan; Shen, Yuping

2017-01-01

Sanghuang is one of mystical traditional Chinese medicines recorded earliest 2000 years ago, that included various fungi of Inonotus genus and was well-known for antitumor effect in modern medicine. Inonotus vaninii is grown in natural forest of Northeastern China merely and used as Sanghuang commercially, but it has no quality control specification until now. This study was to establish a rapid method of two-phase acid hydrolysis followed by reversed phase-high performance liquid chromatography-ultra violet (RP-HPLC-UV) to quantify naringenin in the fruit body of I. vaninii . Sample solution was prepared by pretreatment of raw material in two-phase acid hydrolysis and the hydrolysis technology was optimized. After reconstitution, analysis was performed using RP-HPLC-UV. The method validation was investigated and the naringenin content of sample and comparison were determined. The naringenin was obtained by two-phase acid hydrolysis method, namely, 10.0 g of raw material was hydrolyzed in 200 mL of 1% sulfuric acid aqueous solution (v/v) and 400 mL of chloroform in oil bath at 110°C for 2 h. Good linearity ( r = 0.9992) was achieved between concentration of analyte and peak area. The relative standard deviation (RSD) of precision was 2.47% and the RSD of naringenin contents for repeatability was 3.13%. The accuracy was supported with recoveries at 96.37%, 97.30%, and 99.31%. The sample solution prepared using the proposed method contained higher content of naringenin than conventional method and was stable for 8 h. Due to the high efficiency of sample preparation and high reliability of the HPLC method, it is feasible to use this method for routine analysis of naringenin in the fungus. A convenient two-phase acid hydrolysis was employed to produce naringenin from raw material, and then an efficient and reliable reversed phase-high performance liquid chromatography-ultra violet method was established to monitor naringenin in the fruit bodies of Inonotus vaninii

Dichotomous Effect of Caffeine, Curcumin, and Naringenin on Genomic DNA of Normal and Diabetic Subjects

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Debarati Chattopadhyay

2014-01-01

Full Text Available Nutraceutical compounds show antioxidant and prooxidant properties under stress conditions like cancer, diabetes, and other diseases. The objective of this study is to find the dichotomic behavior of caffeine, curcumin, and naringenin on DNA of diabetic and normal subjects in the presence and absence of copper, hydrogen peroxide, and complex of copper-hydrogen peroxide. Hydrogen peroxide releases hydroxyl free radicals (•OH on oxidation of Cu (I to Cu (II through Fenton-type reaction to cause DNA damage. In the results, agarose gel electrophoretic pattern speculates the prooxidant effect of caffeine and antioxidant effect of curcumin on DNA in the presence of copper and hydrogen peroxide. UV-Vis spectral analysis shows hyperchromism on addition of DNA to caffeine, hypochromism with curcumin, and subtle changes with naringenin. The chosen nutraceuticals act as inducers and quenchers of oxidative free radicals arising from diabetes.

Naringenin (NAR) and 8-prenylnaringenin (8-PN) reduce the developmental competence of porcine oocytes in vitro

NARCIS (Netherlands)

Solak, Kamila A.; Santos, Regiane R.; van den Berg, Martin; Blaauboer, Bas J.; Roelen, Bernard A J; van Duursen, Majorie B M

2014-01-01

Flavanones such as naringenin (NAR) and 8-prenylnaringenin (8-PN) are increasingly used as dietary supplements despite scientific concern regarding adverse effects on female reproduction upon excessive intake. In the present study, NAR and 8-PN (0.3-1. μM) significantly affected porcine oocyte

Discrimination of the rare medicinal plant Dendrobium officinale based on naringenin, bibenzyl, and polysaccharides.

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Chen, Xiaomei; Wang, Fangfei; Wang, Yunqiang; Li, Xuelan; Wang, Airong; Wang, Chunlan; Guo, Shunxing

2012-12-01

The aim of this study was to establish a method for discriminating Dendrobium officinale from four of its close relatives Dendrobium chrysanthum, Dendrobium crystallinum, Dendrobium aphyllum and Dendrobium devonianum based on chemical composition analysis. We analyzed 62 samples of 24 Dendrobium species. High performance liquid chromatography analysis confirmed that the four low molecular weight compounds 4',5,7-trihydroxyflavanone (naringenin), 3,4-dihydroxy-4',5-dime-thoxybibenzyl (DDB-2), 3',4-dihydroxy-3,5'-dimethoxybibenzyl (gigantol), and 4,4'-dihydroxy-3,3',5-trimethoxybibenzy (moscatilin), were common in the genus. The phenol-sulfuric acid method was used to quantify polysaccharides, and the monosaccharide composition of the polysaccharides was determined by gas chromatography. Stepwise discriminant analysis was used to differentiate among the five closely related species based on the chemical composition analysis. This proved to be a simple and accurate approach for discriminating among these species. The results also showed that the polysaccharide content, the amounts of the four low molecular weight compounds, and the mannose to glucose ratio, were important factors for species discriminant. Therefore, we propose that a chemical analysis based on quantification of naringenin, bibenzyl, and polysaccharides is effective for identifying D. officinale.

Grapefruit juice and its constituents augment colchicine intestinal absorption: potential hazardous interaction and the role of p-glycoprotein.

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Dahan, Arik; Amidon, Gordon L

2009-04-01

To investigate the potential interaction between grapefruit juice (GFJ) and the oral microtubule polymerization inhibitor colchicine, a P-gp and CYP3A4 substrate. Colchicine intestinal epithelial transport was investigated across Caco-2 cell monolayers in both AP-BL and BL-AP directions, in the absence/presence of known P-gp inhibitors (verapamil and quinidine). The concentration-dependent effects of GFJ and its major constituents (6'-7'-dihydroxybergamottin, naringin and naringenin) on colchicine Caco-2 mucosal secretion were examined. The effect of GFJ on colchicine intestinal-permeability was then investigated in-situ in the rat perfusion model, in both jejunum and ileum. Colchicine exhibited 20-fold higher BL-AP than AP-BL Caco-2 permeability, indicative of net mucosal secretion, which was reduced by verapamil/quinidine. Colchicine AP-BL permeability was increased and BL-AP was decreased by GFJ in a concentration-dependent manner (IC(50) values of 0.75% and 0.46% respectively), suggesting inhibition of efflux transport, rather than metabolizing enzyme. Similar effects obtained following pre-experiment incubation with GFJ, even though the juice was not present throughout the transepithelial study. 6'-7'-Dihydroxybergamottin, naringin and naringenin displayed concentration-dependent inhibition on colchicine BL-AP secretion (IC(50) values of 90, 592 and 11.6 microM respectively). Ten percent GFJ doubled colchicine rat in-situ ileal permeability, and increased 1.5-fold jejunal permeability. The data suggest that GFJ may augment colchicine oral bioavailability. Due to colchicine narrow therapeutic-index and severely toxic side-effects, awareness of this interaction is prudent.

Protective effects of orange (Citrus sinensis L.) peel aqueous extract and hesperidin on oxidative stress and peptic ulcer induced by alcohol in rat.

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Selmi, Slimen; Rtibi, Kais; Grami, Dhekra; Sebai, Hichem; Marzouki, Lamjed

2017-08-14

Massive alcohol drinking can lead to gastric ulcer. In the present study we investigated the gastroprotective effect of Citrus sinensis peel aqueous extract (CSPE) and Hesperidin (H) in ethanol (EtOH) induced oxidative stress and peptic ulcer in rats. Seventy adult male Wistar rats were divided into seven groups of 10 each: control, EtOH (4 g/kg b.w.), EtOH + various doses of CSPE (100, 200 and 400 mg/kg, b.w.), EtOH + Hesperidin (50 mg/kg, p.o.) and EtOH + Omeprazole (OM, 20 mg/kg, p.o.). Animals were perorally (p.o.) pre-treated with CSPE during 15 days and intoxicated with a single oral administration of EtOH (4 g/kg b.w.) during 2 h. Gastric ulcer was induced in rats with a single dose of ethanol (EtOH). Ulcer index, gene expression of gastric cyclooxygenase-2 (COX-2), tumor necrosis factor alpha (TNF-α), malondialdhyde (MDA), hydrogen peroxide H 2 O 2 and Thiol groups (-SH) content in stomach and antioxidant enzymes superoxide dismutase (SOD), catalase (CAT) and gluthation peroxidise (GPx) were measured. Furthermore, histopathological examinations were performed. The results showed that ethanol induced gastric damage, improving oxidative stress markers level such as MDA (121 ± 4.45 nmol/mg proteins) and H 2 O 2 (24.62 ± 1.04 μmol/mg proteins), increased pro-inflammatory cytokine (TNF-α level), as well as the expression of COX-2 in the ethanol group. However, a significant depletion of enzymatic and non-enzymatic antioxidants were observed, such as, GPx (72%), SOD (57.5%), CAT (41.6%) and -SH (50%). The lesions were associated with severe histopathological damage. The both Citrus sinensis peel aqueous extract (CSPE) and hesperidin significantly protect against all gastric damages caused by ethanol administration in rats. We propose that CSPE and hesperidin exhibit protective effects in EtOH-induced peptic ulcer in rat. This protection might be related in to part its antioxidant properties as well as its opposite effects on some studied

Antimicrobial activity of grapefruit seed and pulp ethanolic extract.

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Cvetnić, Zdenka; Vladimir-Knezević, Sanda

2004-09-01

Antibacterial and antifungal activity of ethanolic extract of grapefruit (Citrus paradisi Macf., Rutaceae) seed and pulp was examined against 20 bacterial and 10 yeast strains. The level of antimicrobial effects was established using an in vitro agar assay and standard broth dilution susceptibility test. The contents of 3.92% of total polyphenols and 0.11% of flavonoids were determined spectrometrically in crude ethanolic extract. The presence of flavanones naringin and hesperidin in the extract was confirmed by TLC analysis. Ethanolic extract exibited the strongest antimicrobial effect against Salmonella enteritidis (MIC 2.06%, m/V). Other tested bacteria and yeasts were sensitive to extract concentrations ranging from 4.13% to 16.50% (m/V).

Transepithelial transport of flavanone in intestinal Caco-2 cell monolayers

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Kobayashi, Shoko; Konishi, Yutaka

2008-01-01

Our recent study [S. Kobayashi, S. Tanabe, M. Sugiyama, Y. Konishi, Transepithelial transport of hesperetin and hesperidin in intestinal Caco-2 cell monolayers, Biochim. Biophys. Acta, 1778 (2008) 33-41] shows that the mechanism of absorption of hesperetin involves both proton-coupled active transport and transcellular passive diffusion. Here, as well as analyzing the cell permeability of hesperetin, we also study the transport of other flavanones, naringenin and eriodictyol, using Caco-2 cell monolayers. Similar to hesperetin mentioned, naringenin and eriodictyol showed proton-coupled polarized transport in apical-to-basolateral direction in non-saturable manner, constant permeation in the apical-to-basolateral direction (J ap→bl ) irrespective of the transepithelial electrical resistance (TER), and preferable distribution into the basolateral side after apical loading in the presence of a proton gradient. Furthermore, the proton-coupled J ap→bl of hesperetin, naringenin and eriodictyol, were inhibited by substrates of the monocarboxylic acid transporter (MCT), such as benzoic acid, but not by ferulic acid. In contrast, both benzoic and ferulic acids have no stimulatory effect on J ap→bl of each flavanone by trans-stimulation analysis. These results indicates that proton-driven active transport is commonly participated in the absorption of flavanone in general, and that its transport is presumed to be unique other than MCT-mediated transport for absorption of phenolic acids (PAs), sodium-dependent MCT (SMCT) nor anion exchanger-mediated transport

Characterization of Sugar and Polyphenolic Diversity in Floral Nectar of Different 'Oblačinska' Sour Cherry Clones.

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Guffa, Basem; Nedić, Nebojša M; Dabić Zagorac, Dragana Č; Tosti, Tomislav B; Gašić, Uroš M; Natić, Maja M; Fotirić Akšić, Milica M

2017-09-01

'Oblačinska' sour cherry, an autochthonous cultivar, is the most planted cultivar in Serbian orchards. Since fruit trees in temperate zone reward insects by producing nectar which 'quality' affects the efficiency of insect pollination, the aim of this study was analyzing of sugars and polyphenolics in floral nectar of 16 'Oblačinska' sour cherry clones with different yielding potential. The contents of sugars and sugar alcohols were analyzed by ion chromatography, while polyphenolic profile was established using liquid chromatography/mass spectrometry technique. Fourteen sugars and six sugar alcohols were detected in nectar samples and the most abundant were fructose, glucose, and sucrose. Eleven polyphenols were quantified using available standards, while another 17 were identified according to their exact masses and characteristic fragmentations. Among quantified polyphenols, rutin, naringenin, and chrysin were the most abundant in nectar. Principal component analysis showed that some polyphenol components (naringin, naringenin, and rutin) together with sugars had high impact of spatial distribution of nectar samples on score plot. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Quantitative analysis of rutin, quercetin, naringenin, and gallic acid by validated RP- and NP-HPTLC methods for quality control of anti-HBV active extract of Guiera senegalensis.

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Alam, Perwez; Parvez, Mohammad K; Arbab, Ahmed H; Al-Dosari, Mohammed S

2017-12-01

Guiera senegalensis J.F. Gmel (Combretaceae) is a folk medicinal plant used in various metabolic and infectious diseases. In addition to its antiviral activities against herpes and fowlpox, the anti-HBV efficacy is very recently reported. To develop and validate simple, sensitive RP-/NP-HPTLC methods for quantitative determination of biomarkers rutin, quercetin, naringenin, and gallic acid in the anti-HBV active G. senegalensis leaves ethanol-extract. RP-HPTLC (rutin & quercetin; phase- acetonitrile:water, 4:6) and NP-HPTLC (naringenin & gallic acid; phase- toluene:ethyl acetate:formic acid, 6:4:0.8) were performed on glass-backed silica gel plates 60F 254 -RP18 and 60F 254 , respectively. The methods were validated according to the ICH guidelines. Well-separated and compact spots (R f ) of rutin (0.52 ± 0.006), quercetin (0.23 ± 0.005), naringenin (0.56 ± 0.009) and gallic acid (0.28 ± 0.006) were detected. The regression equations (Y) were 12.434x + 443.49, 10.08x + 216.85, 11.253x + 973.52 and 11.082x + 446.41 whereas the coefficient correlations (r 2 ) were 0.997 ± 0.0004, 0.9982 ± 0.0001, 0.9974 ± 0.0004 and 0.9981 ± 0.0001, respectively. The linearity ranges (ng/spot) were 200-1400 (RP-HPTLC) and 100-1200 (NP-HPTLC). The LOD/LOQ (ng/band) were 33.03/100.1 (rutin), 9.67/29.31 (quercetin), 35.574/107.8 (naringenin), and 12.32/37.35 (gallic acid). Gallic acid (7.01 μg/mg) was the most abundant biomarker compared to rutin (2.42 μg/mg), quercetin (1.53 μg/mg) and naringenin (0.14 μg/mg) in the extract. The validated NP-/RP-HPTLC methods were simple, accurate, and sensitive for separating and quantifying antiviral biomarkers in G. senegalensis, and endorsed its anti-HBV activity. The developed methods could be further employed in the standardization and quality-control of herbal formulations.

­­The Effects of Naringenin on Some Human Breast Cancer Cells: A Systematic Review

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Zahra Akbarzadeh

2016-06-01

Full Text Available Background: Breast cancer is the most common cancer in women worldwide. Recently, natural remedies such as Naringenin (Nar - a kind of flavonoids which can be found in grapefruits, oranges, and tomatoes - seem to be interesting. They play a useful role in treatment and chemoprevention because of having pleiotropic molecular mechanisms of action on breast cancer cells.Methods: We performed a PRISMA-directed systematic review to investigate the effects of Naringenin on some human breast cancer cells (MCF-7, T47D, and MDA-MB-231. Tumor size, apoptosis, estrogenic properties, and cytotoxicity were assessed as primary outcomes. The systematic search without restriction was conducted in electronic databases, including PubMed, Scopus, Google scholar, and Cochrane Library.Results: Initially, 6445 articles were identified. After screening their titles and abstracts, 32 studies were selected for text appraisal. Finally, 6 articles which met the inclusion criteria were evaluated. Based on the evaluation, Nar could inhibit both cell proliferation and tumor growth at different concentration. Moreover, it could induce apoptosis.Conclusions: Due to anticancer properties of Nar, some probable mechanisms of these effects are induction of alteration in aromatase and caspase enzymes, and suppression of oestrogen signal transduction pathways. However, more investigations are necessary in the future to decide whether Nar consumption is recommendable as part of breast cancer treatment and control. Also, some clinical trials should be designed to determine the optimal dose for the therapeutic use.

Metabonomics Combined with UPLC-MS Chemical Profile for Discovery of Antidepressant Ingredients of a Traditional Chinese Medicines Formula, Chaihu-Shu-Gan-San

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Hongmei Jia

2013-01-01

Full Text Available This study proposed a new strategy for uncovering the active chemical constituents of a traditional Chinese medicines (TCMs formula, Chaihu-Shu-Gan-San (CSGS. Metabonomics and chemical profile were integrated in combination with the multivariate statistical analysis (MVA to discover the chemical constituents which contribute to the antidepressant effect of CSGS. Based upon the difference between CSGS and QZ (CSGS without Zhi-Qiao extracts in the chemical profiles and the regulations of metabolic disturbances induced by CUMS, synephrine, naringin, hesperidin, and neohesperidin were recognized as the active constituents of CSGS from Zhi-qiao responsible for those missing regulations of CSGS when Zhi-Qiao was subtracted from the whole formula. They participated in the regulations of the deviated metabolites 2–4, 10–14, and 22–25, involved in metabolic pathways of ketone bodies synthesis, phenylalanine, tyrosine and tryptophan biosynthesis, valine, aspartate, glutamate metabolism, and glycolysis/gluconeogenesis. Furthermore, the assay of MAO-A activity confirmed the potential antidepressant effect of naringin and its active sites on the MAO-A was inferred by molecular docking study. The integration of metabonomics and chemical profile was proved to be a useful strategy for uncovering what the active chemical constituents in TCM formula are and how they make contributions for the efficacy of the formula.

The place of Ruscus extract, hesperidin methyl chalcone, and vitamin C in the management of chronic venous disease.

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Jawien, Arkadiusz; Bouskela, Eliete; Allaert, François A; Nicolaïdes, Andrew N

2017-02-01

Despite continuous improvement in our knowledge and management of chronic venous disease (CVD), certain areas, such as the role of muscarinic receptors in the pathology and treatment of CVD, remain unexplored. The symposium "The place of Ruscus extract, hesperidin methyl chalcone, and vitamin C in the management of CVD", held at the Annual Meeting of the European Venous Forum on 7-9 July 2016 in London, presented an update on the pathophysiology of CVD and highlighted how the combination of Ruscus extract, hesperidin methyl chalcone, and vitamin C (Ruscus/HMC/VitC; Cyclo 3® Fort), may counteract the deleterious processes underlying CVD. The data presented during this symposium are reported here. The pathophysiology of CVD is driven by a complex process involving numerous factors, with the two key players being venous hypertension and the inflammatory response. The cascade of reactions induced by disturbed venous flow, inflammation, and tissue alterations results in the early appearance of symptoms and progressive development of clinical signs of disease. Previous studies have shown that Ruscus extract acts at three levels: on the veins, capillaries and lymphatics, and has anti-inflammatory properties. A series of recent experiments has shed new light on the mechanism of action of the combination of Ruscus/HMC/VitC. The efficacy of Ruscus/HMC/VitC in CVD is supported by clinical studies, while two meta-analyses have confirmed a significant decrease of several symptoms and ankle circumference in response to treatment with this agent, leading to the conclusion that Ruscus/HMC/VitC deserves a Grade A rating.

Introduction of distillate rosemary leaves into the diet of the Murciano-Granadina goat: transfer of polyphenolic compounds to goats' milk and the plasma of suckling goat kids.

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Jordán, Maria José; Moñino, María Inmaculada; Martínez, Cristina; Lafuente, Arturo; Sotomayor, José Antonio

2010-07-28

The effect of the introduction of distilled rosemary leaves into the diet of the Murciano-Granadina goat on the polyphenolic profile of the goats' milk during the physiological stages of gestation and lactation was studied. The inclusion of rosemary leaves into the animal diet modified neither animal productivity (milk yield) nor milk quality. The following components were found in increased concentration (P goats' milk after the introduction of rosemary leaves into their diet: flavonoids hesperidin, naringin, and genkwanin; gallic acid; and phenolic diterpenes carnosol and carnosic acid. With regard to the transfer of polyphenols to the plasma of the suckling goat kid, a statistically significant increase (P goats' milk and allow for an increased concentration of polyphenolic components in the goats' milk and in the plasma of the suckling goat kid.

Gelidium elegans, an edible red seaweed, and hesperidin inhibit lipid accumulation and production of reactive oxygen species and reactive nitrogen species in 3T3-L1 and RAW264.7 cells.

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Jeon, Hui-Jeon; Seo, Min-Jung; Choi, Hyeon-Son; Lee, Ok-Hwan; Lee, Boo-Yong

2014-11-01

Gelidium elegans is an edible red alga native to the intertidal area of northeastern Asia. We investigated the effect of G. elegans extract and its main flavonoids, rutin and hesperidin, on lipid accumulation and the production of reactive oxygen species (ROS) and reactive nitrogen species (RNS) in 3T3-L1 and RAW264.7 cells. Our data show that G. elegans extract decreased lipid accumulation and ROS/RNS production in a dose-dependent manner. The extract also inhibited the mRNA expression of adipogenic transcription factors, such as peroxisome proliferator-activated receptor gamma and CCAAT/enhancer-binding protein alpha, while enhancing the protein expression of the antioxidant enzymes superoxide dismutases 1 and 2, glutathione peroxidase, and glutathione reductase compared with controls. In addition, lipopolysaccharide-induced nitric oxide production was significantly reduced in G. elegans extract-treated RAW264.7 cells. In analysis of the effects of G. elegans flavonoids on lipid accumulation and ROS/RNS production, only hesperidin showed an inhibitory effect on lipid accumulation and ROS production; rutin did not affect adipogenesis and ROS status. The antiadipogenic effect of hesperidin was evidenced by the downregulation of peroxisome proliferator-activated receptor gamma, CCAAT/enhancer-binding protein alpha, and fatty acid binding protein 4 gene expression. Collectively, our data suggest that G. elegans is a potential food source containing antiobesity and antioxidant constituents. Copyright © 2014 John Wiley & Sons, Ltd.

Naringenin and quercetin--potential anti-HCV agents for NS2 protease targets.

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Lulu, S Sajitha; Thabitha, A; Vino, S; Priya, A Mohana; Rout, Madhusmita

2016-01-01

Nonstructural proteins of hepatitis C virus had drawn much attention for the scientific fraternity in drug discovery due to its important role in the disease. 3D structure of the protein was predicted using molecular modelling protocol. Docking studies of 10 medicinal plant compounds and three drugs available in the market (control) with NS2 protease were employed by using rigid docking approach of AutoDock 4.2. Among the molecules tested for docking study, naringenin and quercetin revealed minimum binding energy of - 7.97 and - 7.95 kcal/mol with NS2 protease. All the ligands were docked deeply within the binding pocket region of the protein. The docking study results showed that these compounds are potential inhibitors of the target; and also all these docked compounds have good inhibition constant, vdW+Hbond+desolv energy with best RMSD value.

Simultaneous Quantification of Seven Bioactive Flavonoids in Citri Reticulatae Pericarpium by Ultra-Fast Liquid Chromatography Coupled with Tandem Mass Spectrometry.

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Zhao, Lian-Hua; Zhao, Hong-Zheng; Zhao, Xue; Kong, Wei-Jun; Hu, Yi-Chen; Yang, Shi-Hai; Yang, Mei-Hua

2016-05-01

Citri Reticulatae Pericarpium (CRP) is a commonly-used traditional Chinese medicine with flavonoids as the major bioactive components. Nevertheless, the contents of the flavonoids in CRP of different sources may significantly vary affecting their therapeutic effects. Thus, the setting up of a reliable and comprehensive quality assessment method for flavonoids in CRP is necessary. To set up a rapid and sensitive ultra-fast liquid chromatography coupled with tandem mass spectrometry (UFLC-MS/MS) method for simultaneous quantification of seven bioactive flavonoids in CRP. A UFLC-MS/MS method coupled to ultrasound-assisted extraction was developed for simultaneous separation and quantification of seven flavonoids including hesperidin, neohesperidin, naringin, narirutin, tangeretin, nobiletin and sinensetin in 16 batches of CRP samples from different sources in China. The established method showed good linearity for all analytes with correlation coefficient (R) over 0.9980, together with satisfactory accuracy, precision and reproducibility. Furthermore, the recoveries at the three spiked levels were higher than 89.71% with relative standard deviations (RSDs) lower than 5.19%. The results indicated that the contents of seven bioactive flavonoids in CRP varied significantly among different sources. Among the samples under study, hesperidin showed the highest contents in 16 samples ranged from 27.50 to 86.30 mg/g, the contents of hesperidin in CRP-15 and CRP-9 were 27.50 and 86.30 mg/g, respectively, while, the amount of narirutin was too low to be measured in some samples. This study revealed that the developed UFLC-MS/MS method was simple, sensitive and reliable for simultaneous quantification of multi-components in CRP with potential perspective for quality control of complex matrices. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

Determination of total antioxidant capacity by a new spectrophotometric method based on Ce(IV) reducing capacity measurement.

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Ozyurt, Dilek; Demirata, Birsen; Apak, Resat

2007-02-28

Dietary antioxidants widely found in fruits and vegetables may serve the task of reducing oxidative damage in humans induced by free radicals and reactive oxygen species under 'oxidative stress' conditions. The aim of this work is to develop a simple, low-cost, sensitive, and diversely applicable indirect spectrophotometric method for the determination of total antioxidant capacity of several plants. The method is based on the oxidation of antioxidants with cerium(IV) sulfate in dilute sulfuric acid at room temperature. The Ce(IV) reducing capacity of the sample is measured under carefully adjusted conditions of oxidant concentration and pH such that only antioxidants and not other organic compounds would be oxidized. The spectrophotometric determination of the remaining Ce(IV) was performed after completion of reaction with antioxidants. Quercetin and gallic acid were used as standards for flavonoids and phenolic acids, respectively, and results of antioxidant measurements were reported as trolox equivalents. The developed procedure was successfully applied to the assay of total antioxidant capacity due to simple compounds such as trolox, quercetin, gallic acid, ascorbic acid, catechin, naringin, naringenin, caffeic acid, chlorogenic acid, ferulic acid, and p-coumaric acid, and due to phenolic acids and flavonoids in the arieal parts of nettle (Urtica Dioica L.). Blank correction of significantly absorbing plant extracts at 320nm could be made with the aid of spectrophotometric titration. Plant selection was made in respect to high antioxidant content, and extraction was made with water. The proposed method was reproducible, and the trolox equivalent antioxidant capacities (TEAC coefficients) of the tested antioxidant compounds were correlated to those found by reference methods such as ABTS and CUPRAC. Since the TEAC coefficients found with the proposed method of naringin-naringenin and rutin-catechin pairs were close to each other, this Ce(IV)-based assay

Neuromodulatory Effects of Hesperidin in Mitigating Oxidative Stress in Streptozotocin Induced Diabetes

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Mohammad Ashafaq

2014-01-01

Full Text Available Oxidative stress has been implicated in pathogenesis of streptozotocin- (STZ- induced diabetes mellitus and its complication in central nervous system (CNS. Recent studies have provided insights on antioxidants and their emergence as potential therapeutic and nutraceutical. The present study examined the hypothesis that hesperidin (HP ameliorates oxidative stress and may be a limiting factor in the extent of CNS complication following diabetes. To test this hypothesis rats were divided into four groups: control, diabetic, diabetic-HP treated, and vehicle for HP treatment group. Diabetes mellitus was induced by a single injection of STZ (65 mg/kg body weight. Three days after STZ injection, HP was given (50 mg/kg b.wt. orally once daily for four weeks. The results of the present investigation suggest that the significant elevated levels of oxidative stress markers were observed in STZ-treated animals, whereas significant depletion in the activity of nonenzymatic antioxidants and enzymatic antioxidants was witnessed in diabetic rat brain. Neurotoxicity biomarker activity was also altered significantly. HP treatment significantly attenuated the altered levels of oxidative stress and neurotoxicity biomarkers. Our results demonstrate that HP exhibits potent antioxidant and neuroprotective effects on the brain tissue against the diabetic oxidative damage in STZ-induced rodent model.

In vitro interactions with repeated grapefruit juice administration--to peel or not to peel?

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Brill, Shlomo; Zimmermann, Christian; Berger, Karin; Drewe, Juergen; Gutmann, Heike

2009-03-01

Interactions of acutely administered grapefruit juice (GFJ) with cytochrome P450 isoform 3A4 (CYP3A4) and P-glycoprotein (Pgp) function are well established. In this study, we investigated in vitro the effect of repeated administration of GFJ and its major constituents (the flavonoid naringin, its aglycone naringenin and the furanocoumarin bergamottin) on mRNA expression of MDR1 and CYP3A4 in LS180 cells. Since the bergamottin content is higher in the peel than in the fruit, we compared GFJ containing peel (GFJP+) with juice without any peel extract (GFJP-). GFJP- (1%) showed no significant effect on MDR1 and CYP3A4 mRNA expression, whereas 1% GFJP+ increased expression of MDR1 3.7-fold (Pextract may have a lower potential for interactions with CYP3A4 or P-glycoprotein.

Naringin Dihydrochalcone Ameliorates Cognitive Deficits and Neuropathology in APP/PS1 Transgenic Mice

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Wenjuan Yang

2018-06-01

Full Text Available Alzheimer’s disease (AD is a multi-factorial neurodegenerative disorder with abnormal accumulation of amyloid-β (Aβ plaques, neuroinflammation and impaired neurogenesis. Mounting evidences suggest that single-target drugs have limited effects on clinical treatment and alternative or multiple targets are required. In recent decades, natural compounds and their derivatives have gained increasing attention in AD drug discovery due to their inherently enormous chemical and structural diversity. In this study, we demonstrated that naringin dihydrochalcone (NDC, a widely used dietary sweetener with strong antioxidant activity, improved the cognitive function of transgenic AD mice. Pathologically, NDC attenuated Aβ deposition in AD mouse brain. Furthermore, NDC reduced periplaque activated microglia and astrocytes, indicating the inhibition of neuroinflammation. It also enhanced neurogenesis as investigated by BrdU/NeuN double labeling. Additionally, the inhibition of Aβ level and neuroinflammation by NDC treatment was also observed in an AD cell model or a microglia cell line. Taken together, our study indicated that NDC might be a potential therapeutic agent for the treatment of AD against multiple targets that include Aβ pathology, neuroinflammation and neurogenesis.

A NodD-like protein activates transcription of genes involved with naringenin degradation in a flavonoid-dependent manner in Herbaspirillum seropedicae.

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Wassem, R; Marin, A M; Daddaoua, A; Monteiro, R A; Chubatsu, L S; Ramos, J L; Deakin, W J; Broughton, W J; Pedrosa, F O; Souza, E M

2017-03-01

Herbaspirillum seropedicae is an associative, endophytic non-nodulating diazotrophic bacterium that colonises several grasses. An ORF encoding a LysR-type transcriptional regulator, very similar to NodD proteins of rhizobia, was identified in its genome. This nodD-like gene, named fdeR, is divergently transcribed from an operon encoding enzymes involved in flavonoid degradation (fde operon). Apigenin, chrysin, luteolin and naringenin strongly induce transcription of the fde operon, but not that of the fdeR, in an FdeR-dependent manner. The intergenic region between fdeR and fdeA contains several generic LysR consensus sequences (T-N 11 -A) and we propose a binding site for FdeR, which is conserved in other bacteria. DNase I foot-printing revealed that the interaction with the FdeR binding site is modified by the four flavonoids that stimulate transcription of the fde operon. Moreover, FdeR binds naringenin and chrysin as shown by isothermal titration calorimetry. Interestingly, FdeR also binds in vitro to the nod-box from the nodABC operon of Rhizobium sp. NGR234 and is able to activate its transcription in vivo. These results show that FdeR exhibits two features of rhizobial NodD proteins: nod-box recognition and flavonoid-dependent transcription activation, but its role in H. seropedicae and related organisms seems to have evolved to control flavonoid metabolism. © 2016 Society for Applied Microbiology and John Wiley & Sons Ltd.

Discovery of potent and selective acetylcholinesterase (AChE) inhibitors: acacetin 7-O-methyl ether Mannich base derivatives synthesised from easy access natural product naringin.

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Liu, Hao-Ran; Men, Xue; Gao, Xiao-Hui; Liu, Lin-Bo; Fan, Hao-Qun; Xia, Xin-Hua; Wang, Qiu-An

2018-03-01

Naringin, as a component universal existing in the peel of some fruits or medicinal plants, was usually selected as the material to synthesise bioactive derivates since it was easy to gain with low cost. In present investigation, eight new acacetin-7-O-methyl ether Mannich base derivatives (1-8) were synthesised from naringin. The bioactivity evaluation revealed that most of them exhibited moderate or potent acetylcholinesterase (AChE) inhibitory activity. Among them, compound 7 (IC 50 for AChE = 0.82 ± 0.08 μmol•L -1 , IC 50 for BuChE = 46.30 ± 3.26 μmol•L -1 ) showed a potent activity and high selectivity compared with the positive control Rivastigmine (IC 50 for AChE = 10.54 ± 0.86 μmol•L -1 , IC 50 for BuChE = 0.26 ± 0.08 μmol•L -1 ). The kinetic study suggested that compound 7 bind to AChE with mix-type inhibitory profile. Molecular docking study revealed that compound 7 could combine both catalytic active site (CAS) and peripheral active site (PAS) of AChE with four points (Trp84, Trp279, Tyr70 and Phe330), while it could bind with BuChE via only His 20.

BIOPHOTOVOLTAIC TIPE-N DAN TIPE-P DENGAN MENGGUNAKAN EKSTRAK KULIT JERUK DARI ACEH

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Luthviyah Choirotul Muhimah

2017-11-01

Full Text Available Sel surya berpewarna tersensitisasi atau dikenal dengan dye-sensitized solar cell (DSSC dengan menggunakan semikonduktor tipe-n dan tipe-p serta ekstrak jeruk Mentui (khas Aceh sebagai biomolekul pewarna sensitisasi (dye telah difabrikasi dan dikarakterisasi. Sebagai pembanding, ekstrak jeruk nipis dan jeruk purut juga digunakan. Ekstrak jeruk mentui berdasarkan spektrum inframerah mengandung berbagai macam karotenoid dan flavonoid seperti beta karoten, hesperidin, lutein, naringin, quersetin, tangeretin, dan zeaxanthin. Karakteristik optik ekstrak jeruk Mentui juga menunjukkan nilai absorptivitas molar yang cukup tinggi sehingga dapat digunakan untuk pembuatan DSSC. Hasil pengujian arus-tegangan menunjukkan hasil bahwa penggunaan ekstrak jeruk Mentui pada semikonduktor tipe-n mampu menghasilkan efisiensi yang lebih besar daripada semikonduktor tipe-p. Adapun tegangan rangkaian terbuka (VOC dan faktor pengisian (fill factor, FF relatif sama untuk semua jenis ekstrak jeruk yaitu VOC ~ 0.340 V dan FF ~ 0.4. Rapat arus pada rangkaian singkat terbesar (Jsc = 1.21 mA·cm-2 dihasilkan DSSC dengan molekul pewarna ekstrak jeruk mentui.

Brain-targeted delivery of trans-activating transcriptor-conjugated magnetic PLGA/lipid nanoparticles.

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Xiangru Wen

Full Text Available Magnetic poly (D,L-lactide-co-glycolide (PLGA/lipid nanoparticles (MPLs were fabricated from PLGA, L-α-phosphatidylethanolamine (DOPE, 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-amino (polyethylene glycol (DSPE-PEG-NH2, and magnetic nanoparticles (NPs, and then conjugated to trans-activating transcriptor (TAT peptide. The TAT-MPLs were designed to target the brain by magnetic guidance and TAT conjugation. The drugs hesperidin (HES, naringin (NAR, and glutathione (GSH were encapsulated in MPLs with drug loading capacity (>10% and drug encapsulation efficiency (>90%. The therapeutic efficacy of the drug-loaded TAT-MPLs in bEnd.3 cells was compared with that of drug-loaded MPLs. The cells accumulated higher levels of TAT-MPLs than MPLs. In addition, the accumulation of QD-loaded fluorescein isothiocyanate (FITC-labeled TAT-MPLs in bEnd.3 cells was dose and time dependent. Our results show that TAT-conjugated MPLs may function as an effective drug delivery system that crosses the blood brain barrier to the brain.

HL-60 differentiating activity and flavonoid content of the readily extractable fraction prepared from citrus juices.

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Kawaii, S; Tomono, Y; Katase, E; Ogawa, K; Yano, M

1999-01-01

Citrus plants are rich sources of various bioactive flavonoids. To eliminate masking effects caused by hesperidin, naringin, and neoeriocitrin, the abundant flavonoid glycosides which make up 90% of the conventionally prepared sample, the readily extractable fraction from Citrus juice was prepared by adsorbing on HP-20 resin and eluting with EtOH and acetone from the resin and was subjected to HL-60 differentiation assay and quantitative analysis of major flavonoids. Screening of 34 Citrus juices indicated that King (C. nobilis) had a potent activity for inducing differentiation of HL-60, and the active principles were isolated and identified as four polymethoxylated flavonoids, namely, nobiletin, 3,3',4',5,6,7, 8-heptamethoxyflavone, natsudaidain, and tangeretin. HPLC analysis of the readily extractable fraction also indicated that King contained high amounts of these polymethoxylated flavonoids among the Citrus juices examined. Principal component and cluster analyses of the readily extractable flavonoids indicated peculiarities of King and Bergamot.

Visible light assisted photodecolorization of eosin-Y in aqueous solution using hesperidin modified TiO2 nanoparticles

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Vignesh, K.; Suganthi, A.; Rajarajan, M.; Sakthivadivel, R.

2012-03-01

Hesperidin a flavanoid, modified TiO2 nanoparticles (Hes-TiO2) was synthesized to improve the visible light driven photocatalytic performance of TiO2. The synthesized nanoparticles were characterized by UV-visible diffuse reflectance spectroscopy (UV-vis-DRS), FT-IR, powder X-ray diffraction (XRD) and scanning electron microscopy (SEM). The photocatalytic activity of Hes-TiO2 was investigated based on the decolorization of eosin-Y under visible light irradiation. Hes-TiO2 showed high efficiency for the decolorization of eosin-Y. The influences of various reaction parameters like effect of pH, catalyst dosage and initial dye concentration on the photocatalytic efficiency were investigated. The adsorption of eosin-Y on Hes-TiO2 was found favorable by the Langmuir approach. The removal percentage of chemical oxygen demand (COD) was determined to evaluate the mineralization of eosin-Y during photodecolorization. Based on the intermediates obtained in the GC-MS spectroscopic technique, a probable degradation mechanism has been proposed.

Visible light assisted photodecolorization of eosin-Y in aqueous solution using hesperidin modified TiO2 nanoparticles

International Nuclear Information System (INIS)

Vignesh, K.; Suganthi, A.; Rajarajan, M.; Sakthivadivel, R.

2012-01-01

Hesperidin a flavanoid, modified TiO 2 nanoparticles (Hes-TiO 2 ) was synthesized to improve the visible light driven photocatalytic performance of TiO 2 . The synthesized nanoparticles were characterized by UV-visible diffuse reflectance spectroscopy (UV-vis-DRS), FT-IR, powder X-ray diffraction (XRD) and scanning electron microscopy (SEM). The photocatalytic activity of Hes-TiO 2 was investigated based on the decolorization of eosin-Y under visible light irradiation. Hes-TiO 2 showed high efficiency for the decolorization of eosin-Y. The influences of various reaction parameters like effect of pH, catalyst dosage and initial dye concentration on the photocatalytic efficiency were investigated. The adsorption of eosin-Y on Hes-TiO 2 was found favorable by the Langmuir approach. The removal percentage of chemical oxygen demand (COD) was determined to evaluate the mineralization of eosin-Y during photodecolorization. Based on the intermediates obtained in the GC-MS spectroscopic technique, a probable degradation mechanism has been proposed.

Modularization and Response Curve Engineering of a Naringenin-Responsive Transcriptional Biosensor.

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De Paepe, Brecht; Maertens, Jo; Vanholme, Bartel; De Mey, Marjan

2018-05-18

To monitor the intra- and extracellular environment of micro-organisms and to adapt their metabolic processes accordingly, scientists are reprogramming nature's myriad of transcriptional regulatory systems into transcriptional biosensors, which are able to detect small molecules and, in response, express specific output signals of choice. However, the naturally occurring response curve, the key characteristic of biosensor circuits, is typically not in line with the requirements for real-life biosensor applications. In this contribution, a natural LysR-type naringenin-responsive biosensor circuit is developed and characterized with Escherichia coli as host organism. Subsequently, this biosensor is dissected into a clearly defined detector and effector module without loss of functionality, and the influence of the expression levels of both modules on the biosensor response characteristics is investigated. Two collections of ten unique synthetic biosensors each are generated. Each collection demonstrates a unique diversity of response curve characteristics spanning a 128-fold change in dynamic and 2.5-fold change in operational ranges and 3-fold change in levels of Noise, fit for a wide range of applications, such as adaptive laboratory evolution, dynamic pathway control and high-throughput screening methods. The established biosensor engineering concepts, and the developed biosensor collections themselves, are of use for the future development and customization of biosensors in general, for the multitude of biosensor applications and as a compelling alternative for the commonly used LacI-, TetR- and AraC-based inducible circuits.

Exploring the Interactions of the Dietary Plant Flavonoids Fisetin and Naringenin with G-Quadruplex and Duplex DNA, Showing Contrasting Binding Behavior: Spectroscopic and Molecular Modeling Approaches.

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Bhattacharjee, Snehasish; Chakraborty, Sandipan; Sengupta, Pradeep K; Bhowmik, Sudipta

2016-09-01

Guanine-rich sequences have the propensity to fold into a four-stranded DNA structure known as a G-quadruplex (G4). G4 forming sequences are abundant in the promoter region of several oncogenes and become a key target for anticancer drug binding. Here we have studied the interactions of two structurally similar dietary plant flavonoids fisetin and naringenin with G4 as well as double stranded (duplex) DNA by using different spectroscopic and modeling techniques. Our study demonstrates the differential binding ability of the two flavonoids with G4 and duplex DNA. Fisetin more strongly interacts with parallel G4 structure than duplex DNA, whereas naringenin shows stronger binding affinity to duplex rather than G4 DNA. Molecular docking results also corroborate our spectroscopic results, and it was found that both of the ligands are stacked externally in the G4 DNA structure. C-ring planarity of the flavonoid structure appears to be a crucial factor for preferential G4 DNA recognition of flavonoids. The goal of this study is to explore the critical effects of small differences in the structure of closely similar chemical classes of such small molecules (flavonoids) which lead to the contrasting binding properties with the two different forms of DNA. The resulting insights may be expected to facilitate the designing of the highly selective G4 DNA binders based on flavonoid scaffolds.

Visible light assisted photodecolorization of eosin-Y in aqueous solution using hesperidin modified TiO{sub 2} nanoparticles

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Vignesh, K. [P.G. and Research Department of Chemistry, Thiagarajar College, Madurai, Tamilnadu 625009 (India); Suganthi, A., E-mail: suganthiphd09@gmail.com [P.G. and Research Department of Chemistry, Thiagarajar College, Madurai, Tamilnadu 625009 (India); Rajarajan, M., E-mail: rajarajan_1962@yahoo.com [Department of Chemistry, C.P.A. College, Bodinayakanur, Tamilnadu 626513 (India); Sakthivadivel, R. [P.G. and Research Department of Chemistry, Thiagarajar College, Madurai, Tamilnadu 625009 (India)

2012-03-01

Hesperidin a flavanoid, modified TiO{sub 2} nanoparticles (Hes-TiO{sub 2}) was synthesized to improve the visible light driven photocatalytic performance of TiO{sub 2}. The synthesized nanoparticles were characterized by UV-visible diffuse reflectance spectroscopy (UV-vis-DRS), FT-IR, powder X-ray diffraction (XRD) and scanning electron microscopy (SEM). The photocatalytic activity of Hes-TiO{sub 2} was investigated based on the decolorization of eosin-Y under visible light irradiation. Hes-TiO{sub 2} showed high efficiency for the decolorization of eosin-Y. The influences of various reaction parameters like effect of pH, catalyst dosage and initial dye concentration on the photocatalytic efficiency were investigated. The adsorption of eosin-Y on Hes-TiO{sub 2} was found favorable by the Langmuir approach. The removal percentage of chemical oxygen demand (COD) was determined to evaluate the mineralization of eosin-Y during photodecolorization. Based on the intermediates obtained in the GC-MS spectroscopic technique, a probable degradation mechanism has been proposed.

Naringenin decreases invasiveness and metastasis by inhibiting TGF-β-induced epithelial to mesenchymal transition in pancreatic cancer cells.

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Changjie Lou

Full Text Available Epithelial to mesenchymal transition (EMT promotes cellular motility, invasiveness and metastasis during embryonic development and tumorigenesis. Transforming growth factor-β (TGF-β signaling pathway is a key regulator of EMT. A lot of evidences suggest that this process is Smad3-dependent. Herein we showed that exposure of aspc-1 and panc-1 pancreatic cancer cells to TGF-β1 resulted in characteristic morphological alterations of EMT, and enhancement of cell motility and gemcitabine (Gem resistance along with an up-regulation of EMT markers genes such as vimentin, N-cadherin, MMP2 and MMP9. Naringenin (Nar down-regulated EMT markers expression in both mRNA and protein levels by inhibiting TGF-β1/Smad3 signal pathway in the pancreatic cancer cells. Consequently, Nar suppressed the cells migration and invasion and reversed their resistance to Gem.

Flavonoid profiling and nodulation of some legumes in response to the allelopathic stress of Sonchus oleraceus L.

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Nasr Hassan Gomaa

2015-12-01

Full Text Available Annual sowthistle (Sonchus oleraceus has been reported to produce allelopathic effects. Two greenhouse experiments were conducted to estimate the allelopathic potential of both plant residue and root exudates of S. oleraceus on flavonoid composition and nodulation in a leguminous crop, Trifolium alexandrinum, and in two leguminous weeds, Melilotus indicus and T. resupinatum. The results of high performance liquid chromatography-mass spectrometry (HPLC-MS/MS showed that all three legumes contained six flavonoid aglycones: apigenin, daidzein, kaempferol, luteolin, myricetin and quercetin; and seven flavonoid glycosides: daidzin, genistin, hesperidin, hyperoside, kaempferol-7-O-glucoside, naringin and rutin. In general, both plant residue and root exudates had inhibitory effects on the flavonoid composition and nodulation of the target species. However, residue of S. oleraceus caused a significant increase in both individual and total detected flavonoids in T. alexandrinum. The results suggest that the phytotoxins released from S. oleraceus may restrain the biosynthesis of flavonoids in the target species, whereas the accumulated flavonoids in T. alexandrinum are allelopathic-induced metabolites and suggest a resistance mode in this crop.

Naringenin-loaded solid lipid nanoparticles: preparation, controlled delivery, cellular uptake, and pulmonary pharmacokinetics

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Ji P

2016-03-01

Full Text Available Peng Ji, Tong Yu, Ying Liu, Jie Jiang, Jie Xu, Ying Zhao, Yanna Hao, Yang Qiu, Wenming Zhao, Chao WuCollege of Pharmacy, Liaoning Medical University, Jinzhou, Liaoning Province, People’s Republic of ChinaAbstract: Naringenin (NRG, a flavonoid compound, had been reported to exhibit extensive pharmacological effects, but its water solubility and oral bioavailability are only ~46±6 µg/mL and 5.8%, respectively. The purpose of this study is to design and develop NRG-loaded solid lipid nanoparticles (NRG-SLNs to provide prolonged and sustained drug release, with improved stability, involving nontoxic nanocarriers, and increase the bioavailability by means of pulmonary administration. Initially, a group contribution method was used to screen the best solid lipid matrix for the preparation of SLNs. NRG-SLNs were prepared by an emulsification and low-temperature solidification method and optimized using an orthogonal experiment approach. The morphology was examined by transmission electron microscopy, and the particle size and zeta potential were determined by photon correlation spectroscopy. The total drug content of NRG-SLNs was measured by high-performance liquid chromatography, and the encapsulation efficiency (EE was determined by Sephadex gel-50 chromatography and high-performance liquid chromatography. The in vitro NRG release studies were carried out using a dialysis bag. The best cryoprotectant to prepare NRG-SLN lyophilized powder for future structural characterization was selected using differential scanning calorimetry, powder X-ray diffraction, and Fourier transform infrared spectroscopy. The short-term stability, 3-(4,5-dimethylthiazol-2-yl-2,5-diphenyl-tetrazolium bromide (MTT assay, cellular uptake, and pharmacokinetics in rats were studied after pulmonary administration of NRG-SLN lyophilized powder. Glycerol monostearate was selected to prepare SLNs, and the optimal formulation of NRG-SLNs was spherical in shape, with a particle

Anticoccidial efficacy of naringenin and a grapefruit peel extract in growing lambs naturally-infected with Eimeria spp.

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Pérez-Fonseca, Agustín; Alcala-Canto, Yazmin; Salem, Abdelfattah Z M; Alberti-Navarro, Aldo B

2016-12-15

The current study aimed to determine the anti-Eimeria efficacy of an extract of grapefruit peels (GF) and commercial naringenin (NAR) in naturally-infected lambs, as well as the influence of these flavonoids on the oxidative status during ovine coccidiosis. Pharmacokinetic profiles were also determined. Extracts were administered per os to Eimeria naturally infected growing lambs during 90 consecutive days. The commercial anticoccidial drug toltrazuril (TTZ) was included in this trial as a standard. Twenty-four lambs were divided into four groups: NAR, lambs given a daily dose of 5mg of a commercial naringenin extract of 98% higher purity per kg body weight; GF, lambs that recived a daily dose of 5mg of ethanolic extract of grapefruit peels per kg body weight; TTZ, lambs treated with 20mg of toltrazuril/kg body weight on days 0 and 15 of the experiment; and CTRL, untreated lambs that received daily dose of 30ml of water. Daily doses of GF and NAR were dissolved in 30ml of water and orally given to animals; whereas toltrazuril was administered as a single dose of an undiluted suspension to lambs of the TTZ group. The CTRL group received 30ml of water; as well as the TTZ group for the period after the single dose administration. Fecal and serum samples were collected from all lambs. Anticoccidial efficacy was estimated by coprological techniques. Generation of nitric oxide levels and the antioxidant capacity of the experimental compounds were determined by the Griess and ABTS assays, respectively. The pharmacokinetic parameters of NAR and the GF extract were obtained. On day 30 post-ingestion, anticoccidial efficacy was 91.76% (NAR) and 89.65% (GF); whereas 99.63% of efficacy was achieved with TTZ 15days after treatment. NAR, GF and TTZ significantly reduced oxidative stress in infected animals. The mean daily weight gain for each group was 122g (NAR), 122g (GF), 143g (TTZ) and 98g (CTRL). Following the oral administration of NAR and GF, values in plasma approached

Hesperidin as radioprotector against radiation-induced lung damage in rat: A histopathological study

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Gholam Hassan Haddadi

2017-01-01

Full Text Available Reactive oxygen species (ROS are generated by ionizing radiation, and one of the organs commonly affected by ROS is the lung. Radiation-induced lung injury including pneumonia and lung fibrosis is a dose-limiting factor in radiotherapy (RT of patients with thorax irradiation. Administration of antioxidants has been proved to protect against ROS. The present study was aimed to assess the protective effect of hesperidin (HES against radiation-induced lung injury of male rats. Fifty rats were divided into three groups. G1: Received no HES and radiation (sham. G2: Underwent γ-irradiation to the thorax. G3: Received HES and underwent γ-irradiation. The rats were exposed to a single dose of 18 Gy using cobalt-60 unit and were administered HES (100 mg/kg for 7 days before irradiation. Histopathological analysis was performed 24 h and 8 weeks after RT. Histopathological results in 24 h showed radiation-induced inflammation and presence of more inflammatory cells as compared to G1 (P < 0.05. Administration of HES significantly decreased such an effect when compared to G2 (P < 0.05. Histopathological evaluation in 8 weeks showed a significant increase in mast cells, inflammation, inflammatory cells, alveolar thickness, vascular thickness, pulmonary edema, and fibrosis in G2 when compared to G1 (P < 0.05. HES significantly decreased inflammatory response, fibrosis, and mast cells when compared to G2 (P < 0.05. Administration of HES resulted in decreased radiation pneumonitis and radiation fibrosis in the lung tissue. Thus, the present study showed HES to be an efficient radioprotector against radiation-induced damage in the lung of tissue rats.

Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.

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Uckoo, Ram M; Jayaprakasha, Guddadarangavvanahally K; Balasubramaniam, V M; Patil, Bhimanagouda S

2012-09-01

Grapefruits (Citrus paradisi Macfad) contain several phytochemicals known to have health maintaining properties. Due to the consumer's interest in obtaining high levels of these phytochemicals, it is important to understand the changes in their levels by common household processing techniques. Therefore, mature Texas "Rio Red" grapefruits were processed by some of the common household processing practices such as blending, juicing, and hand squeezing techniques and analyzed for their phytochemical content by high performance liquid chromatography (HPLC). Results suggest that grapefruit juice processed by blending had significantly (P levels of flavonoids (narirutin, naringin, hesperidin, neohesperidin, didymin, and poncirin) and limonin compared to juicing and hand squeezing. No significant variation in their content was noticed in the juice processed by juicing and hand squeezing. Ascorbic acid and citric acid were significantly (P processed by juicing and blending, respectively. Furthermore, hand squeezed fruit juice had significantly higher contents of dihydroxybergamottin (DHB) than juice processed by juicing and blending. Bergamottin and 5-methoxy-7 gernoxycoumarin (5-M-7-GC) were significantly higher in blended juice compared to juicing and hand squeezing. Therefore, consuming grapefruit juice processed by blending may provide higher levels of health beneficial phytochemicals such as naringin, narirutin, and poncirin. In contrast, juice processed by hand squeezing and juicing provides lower levels of limonin, bergamottin, and 5-M-7-GC. These results suggest that, processing techniques significantly influence the levels of phytochemicals and blending is a better technique for obtaining higher levels of health beneficial phytochemicals from grapefruits. Practical Application:  Blending, squeezing, and juicing are common household processing techniques used for obtaining fresh grapefruit juice. Understanding the levels of health beneficial phytochemicals

Development and Validation of Liquid Chromatographic Method for Estimation of Naringin in Nanoformulation

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Kranti P. Musmade

2014-01-01

Full Text Available A simple, precise, accurate, rapid, and sensitive reverse phase high performance liquid chromatography (RP-HPLC method with UV detection has been developed and validated for quantification of naringin (NAR in novel pharmaceutical formulation. NAR is a polyphenolic flavonoid present in most of the citrus plants having variety of pharmacological activities. Method optimization was carried out by considering the various parameters such as effect of pH and column. The analyte was separated by employing a C18 (250.0 × 4.6 mm, 5 μm column at ambient temperature in isocratic conditions using phosphate buffer pH 3.5: acetonitrile (75 : 25% v/v as mobile phase pumped at a flow rate of 1.0 mL/min. UV detection was carried out at 282 nm. The developed method was validated according to ICH guidelines Q2(R1. The method was found to be precise and accurate on statistical evaluation with a linearity range of 0.1 to 20.0 μg/mL for NAR. The intra- and interday precision studies showed good reproducibility with coefficients of variation (CV less than 1.0%. The mean recovery of NAR was found to be 99.33 ± 0.16%. The proposed method was found to be highly accurate, sensitive, and robust. The proposed liquid chromatographic method was successfully employed for the routine analysis of said compound in developed novel nanopharmaceuticals. The presence of excipients did not show any interference on the determination of NAR, indicating method specificity.

Free and Bound Phenolic Compound Content and Antioxidant Activity of Different Cultivated Blue Highland Barley Varieties from the Qinghai-Tibet Plateau.

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Yang, Xi-Juan; Dang, Bin; Fan, Ming-Tao

2018-04-11

In this study, the polyphenols composition and antioxidant properties of 12 blue highland barley varieties planted on the Qinghai-Tibet Plateau area were measured. The contents of the free, bound and total phenolic acids varied between 166.20-237.60, 170.10-240.75 and 336.29-453.94 mg of gallic acid equivalents per 100 g of dry weight (DW) blue highland barley grains, while the free and bound phenolic acids accounted for 50.09% and 49.91% of the total phenolic acids, respectively. The contents of the free, bound and total flavones varied among 20.61-25.59, 14.91-22.38 and 37.91-47.98 mg of catechin equivalents per 100 g of dry weight (DW) of blue highland barley grains, while the free and bound flavones accounted for 55.90% and 44.10% of the total flavones, respectively. The prominent phenolic compounds in the blue hulless barley grains were gallic acid, benzoic acid, syringic acid, 4-coumaric acid, naringenin, hesperidin, rutin, (+)-catechin and quercetin. Among these, protocatechuic acid, chlorogenic acid and (+)-catechin were the major phenolic compounds in the free phenolics extract. The most abundant bound phenolics were gallic acid, benzoic acid, syringic acid, 4-coumaric acid, benzoic acid, dimethoxybenzoic acid, naringenin, hesperidin, quercetin and rutin. The average contribution of the bound phenolic extract to the DPPH • free radical scavenging capacity was higher than 86%, that of free phenolic extract to the ABTS •+ free radical scavenging capacity was higher than 79%, and that of free phenolic (53%) to the FRAP antioxidant activity was equivalent to that of the bound phenol extract (47%). In addition, the planting environment exerts a very important influence on the polyphenol composition, content and antioxidant activity of blue highland barley. The correlation analysis showed that 2,4-hydroxybenzoic acid and protocatechuic acid were the main contributors to the DPPH • and ABTS •+ free radical scavenging capacity in the free phenolic extract

Hesperidin Inhibits Inflammatory Response Induced by Aeromonas hydrophila Infection and Alters CD4+/CD8+ T Cell Ratio

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Abdelaziz S. A. Abuelsaad

2014-01-01

Full Text Available Background. Aeromonas hydrophila is an opportunistic bacterial pathogen that is associated with a number of human diseases. Hesperidin (HES has been reported to exert antioxidant and anti-inflammatory activities. Objectives. The aim of this study was to investigate the potential effect of HES treatment on inflammatory response induced by A. hydrophila infection in murine. Methods. A. hydrophila-infected mice were treated with HES at 250 mg/kg b.wt./week for 4 consecutive weeks. Phagocytosis, reactive oxygen species production, CD4+/CD8+ T cell ratio, and CD14 expression on intestinal infiltrating monocytes were evaluated. The expression of E-selectin and intercellular adhesion molecule 1 on stimulated HUVECs and RAW macrophage was evaluated. Results. Percentage of CD4+ T cells in the intestinal tissues of infected treated mice was highly significantly increased; however, phagocytic index, ROS production, CD8+ T cells percentage, and CD14 expression on monocytes were significantly reduced. On the other hand, HES significantly inhibited A-LPS- and A-ECP-induced E-selectin and ICAM-1 expression on HUVECs and ICAM-1 expression on RAW macrophage. Conclusion. Present data indicated that HES has a potential role in the suppression of inflammatory response induced by A. hydrophila toxins through downmodulation of ROS production and CD14 and adhesion molecules expression, as well as increase of CD4+/CD8+ cell ratio.

Some biological compounds, radical scavenging capacities and antimicrobial activities in the seeds of Nepeta italica L. and Sideritis montana L. sub sp. montana from Turkey

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Emre, I.; Kursat, M.; Yilmaz, O.; Erecevit, P.

2011-07-01

This study determined some biological compounds (fatty acid compositions, lipid-soluble vitamins, sterols, flavonoids), radical scavenging capacities and antimicrobial activities in the seeds of Nepeta italica L. and Sideritis montana L. subsp. montana. It was found that palmitic acid (C16:0; 8.54+-0.13-3.05+-0.04%), oleic acid (C18:1 n9, 22.41+-0.8-18.83+-0.1%) and a-inolenic acid were the dominant fatty acids in both Nepeta italica L. and Sideritis montana L. subsp. montana. It was concluded that both Nepeta italica L. and Sideritis montana L. subsp. montana contained stigmasterol and ergosterol as well as beta-sitosterol. The present findings show that Nepeta italica L. contains morin, catechin, naringin and Sideritis montana L. subsp. montana contains morin, naringenin as major flavonoids. It was also determined that methanol extracts of Nepeta italica L. and Sideritis montana L. subsp. montana were most effective against DPPH radicals. The results of the present study show that the vitamins, flavonoids and fatty acid extracts in the seeds of N. italica L. and S. montana L. subsp. montana prevented the growth of the microorganisms used in the tests at different ratios. (Author).

Trichloroethylene-mediated cytotoxicity in human epidermal keratinocytes is mediated by the rapid accumulation of intracellular calcium: Interception by naringenin.

Science.gov (United States)

Ali, F; Khan, A Q; Khan, R; Sultana, S

2016-02-01

Industrial solvents pose a significant threat to the humankind. The mechanisms of their toxicity still remain in debate. Trichloroethylene (TCE) is a widespread industrial solvent responsible for severe liver dysfunction, cutaneous toxicity in occupationally exposed humans. We utilized an in vitro system of human epidermal keratinocyte (HaCaT) cells in this study to avoid complex cell and extracellular interactions. We report the cytotoxicity of organic solvent TCE in HaCaT and its reversal by a natural flavanone, naringenin (Nar). The cytotoxicity was attributed to the rapid intracellular free calcium (Ca(2+)) release, which might lead to the elevation of protein kinase C along with robust free radical generation, instability due to energy depletion, and sensitization of intracellular stress signal transducer nuclear factor κB. These effects were actually seen to induce significant amount of genomic DNA fragmentation. Furthermore, all these effects of TCE were effectively reversed by the treatment of Nar, a natural flavanone. Our studies identify intracellular Ca as a unique target used by organic solvents in the cytotoxicity and highlight the Ca(2+) ion stabilizer properties of Nar. © The Author(s) 2015.

Identification of the Chemical Constituents in Aqueous Extract of Zhi-Qiao and Evaluation of Its Antidepressant Effect

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Ming Wu

2015-04-01

Full Text Available The immature fruit of Citrus aurantium L. (Zhi-Qiao, ZQ has been used as a traditional medicine in China. Our previous study has shown that ZQ decoction may contribute to the antidepressant-like action of Chaihu-Shu-Gan-San. However, there are no reports on the chemical constituents of ZQ aqueous extract or its anti-depression effects. Firstly, this research reported the on-line identification of the chemical constituents in the aqueous extract of ZQ by coupling ultra-performance liquid chromatography/time-of-flight mass spectrometry (UPLC-Q-TOF/MS. A total of 31 chemical constituents were identified in ZQ aqueous extract, including one tannic acid, five flavones, 13 flavanones, one limonoid, three coumarins, three cyclic peptides, and five polymethoxylated flavonoids. The antidepressant effect of ZQ aqueous extract was evaluated in vivo and the results indicated that the mice immobility time during the forced swimming test and the tail suspension test were significantly reduced with ZQ treatment. MTT assays showed both ZQ aqueous extract and its major constituents (naringin, hesperidin, neohesperidin, and nobiletin had neuroprotective effect on corticosterone-induced neurotoxicity in PC12 cells. The in vivo and in vitro results suggest that ZQ has an antidepressant effect.

Quantitative analysis of the eight major compounds in the Samsoeum using a high-performance liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometer

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Weon, Jin Bae; Yang, Hye Jin; Lee, Bohyoung; Ma, Jin Yeul; Ma, Choong Je

2015-01-01

Background: Samsoeum was traditionally used for treatment of a respiratory disease. Objective: The simultaneous determination of eight major compounds, ginsenoside Rg3, caffeic acid, puerarin, costunolide, hesperidin, naringin, glycyrrhizin, and 6-gingerol in the Samsoeum using a high-performance liquid chromatography (HPLC) coupled with diode array detection (DAD) and an electrospray ionization mass spectrometer was developed for an accurate and reliable quality assessment. Materials and Methods: Eight compounds were qualitative identified based on their mass spectra and by comparing with standard compounds and quantitative analyzed by HPLC-DAD. Separation of eight compounds was carried out on a LUNA C18 column (S-5 μm, 4.6 mm i.d. ×250 mm) with gradient elution composed of acetonitrile and 0.1% trifluoroacetic acid. Results: The data showed good linearity (R2 > 0.9996). The limits of detection and the limits of quantification were <0.53 μg and 1.62 μg, respectively. Inter- and Intra-day precisions (expressed as relative standard deviation values) were within 1.94% and 1.91%, respectively. The recovery of the method was in the range of 94.24–107.90%. Conclusion: The established method is effective and could be applied to quality control of Samsoeum. PMID:25829771

Radioprotective effects of hesperidin on oxidative damages and histopathological changes induced by X-irradiation in rats heart tissue

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Abolhasan Rezaeyan

2016-01-01

Full Text Available This study was carried out to evaluate radioprotective effects of hesperidin (HES administration before the irradiation on the cardiac oxidative stress and histopathological changes in an experimental rat model. The cardiovascular complications of radiation exposure cause morbidity and mortality in patients who received radiotherapy. HES, an antioxidant flavonoid found in citrus fruits, suggests the protection against the tissue damage. Fifty-eight rats were divided into four groups: Group 1 received phosphate buffered saline (PBS and sham radiation; Group 2, HES and sham radiation; Group 3, PBS and radiation; and Group 4, HES and radiation. The rats were exposed to single dose of 18 Gy of 6 MV X-ray. One hundred milligrams per kilogram doses of HES was administered for 7 days before irradiation. The estimation of superoxide dismutase (SOD, malondialdehyde (MDA, and histopathological analyses was performed at 24 h and 8 weeks after radiation exposure. The irradiation of chest area resulted in an elevated MDA level and decreased SOD activity. Moreover, long-term pathological lesions of radiation were inflammation, fibrosis, the increased number of mast cells and macrophages, and development of plaque, vascular leakage, myocardial degeneration, and myocyte necrosis. Although the administration of HES decreases inflammation, fibrosis, mast cell and macrophage numbers, and myocyte necrosis, it did not result in reduced thrombus, myocardium degeneration, and vascular leakage. In conclusion, these results suggest that HES can perform a radioprotection action. The protective effect of HES may be attributable to its immunomodulatory effects and free radical-scavenging properties.

TNF-α Blocker Effect of Naringenin-Loaded Sericin Microparticles that Are Potentially Useful in the Treatment of Psoriasis

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Theodora Chlapanidas

2014-08-01

Full Text Available This study aims to evaluate the effect of combined use of the racemic flavanone Naringenin (NRG and the protein sericin as TNF-α blockers. Sericin (SMs and (R/S NRG-loaded Sericin (SNRGMs microparticles were prepared by spray-drying, characterized in terms of morphology and particle size distribution, and encapsulation efficiency was determined. Concerning morphology and particle size distribution of microparticles, results indicated that they were not affected by the presence of NRG. The encapsulation efficiency was almost quantitative (93%, thus proving that sericin can be advantageously loaded with (R/S NRG. Biological evaluation of (R/S NRG, SMs and SNRGMs was then performed in lipopolysaccharide (LPS-stimulated human peripheral blood mononuclear cells (hPBMC. SNRGMs resulted cytotoxic at the higher dose used (200 μg/mL and the effect was greater than (R/S NRG alone. Moreover, even if sericin alone was not effective in suppressing LPS-induced serum TNF-α levels, SNRGMs loaded with 9.3% of (R/S NRG were significantly more potent than (R/S NRG alone. In summary, this study provides the proof of concept that sericin-based microspheres loaded with TNF-α-blockers could contribute to the down regulation of the cytokine and represents the starting point for the development of new topical formulations for the treatment of middle-stage psoriasis.

Metabolomic profiling of the phytomedicinal constituents of Carica papaya L. leaves and seeds by 1H NMR spectroscopy and multivariate statistical analysis.

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Gogna, Navdeep; Hamid, Neda; Dorai, Kavita

2015-11-10

Extracts from the Carica papaya L. plant are widely reported to contain metabolites with antibacterial, antioxidant and anticancer activity. This study aims to analyze the metabolic profiles of papaya leaves and seeds in order to gain insights into their phytomedicinal constituents. We performed metabolite fingerprinting using 1D and 2D 1H NMR experiments and used multivariate statistical analysis to identify those plant parts that contain the most concentrations of metabolites of phytomedicinal value. Secondary metabolites such as phenyl propanoids, including flavonoids, were found in greater concentrations in the leaves as compared to the seeds. UPLC-ESI-MS verified the presence of significant metabolites in the papaya extracts suggested by the NMR analysis. Interestingly, the concentration of eleven secondary metabolites namely caffeic, cinnamic, chlorogenic, quinic, coumaric, vanillic, and protocatechuic acids, naringenin, hesperidin, rutin, and kaempferol, were higher in young as compared to old papaya leaves. The results of the NMR analysis were corroborated by estimating the total phenolic and flavonoid content of the extracts. Estimation of antioxidant activity in leaves and seed extracts by DPPH and ABTS in-vitro assays and antioxidant capacity in C2C12 cell line also showed that papaya extracts exhibit high antioxidant activity. Copyright © 2015 Elsevier B.V. All rights reserved.

Sadhana | Indian Academy of Sciences

Indian Academy of Sciences (India)

Keywords. Naringin; process development; adsorption; process technology; waste management. Abstract. A process technology has been developed for recovery of naringin from kinnow (citrus) peels,which is a waste. The kinnow peels were boiled with water to extract naringin into water. It was adsorbed on an indigenous ...

Detoxification of Hg(II) from aqueous and enzyme media: Pristine vs. tailored calcium alginate hydrogels.

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Sarkar, Kangkana; Ansari, Zarina; Sen, Kamalika

2016-10-01

Calcium alginate (CA) hydrogels were tailored using phenolic compounds (PC) like, thymol, morin, catechin, hesperidin, during their preparation. The PC incorporated gels show modified surface features as indicated by scanning electron microscopic images (SEM). The rheological studies show that excepting the hesperidin incorporated gels all the other kinds including calcium alginate pristine have similar mechanical strength. The hesperidine incorporated CA gels had the maximum capacity to adsorb Hg. The Freundlich adsorption isotherms show higher values of adsorption capacity for all PC incorporated CA beads than the pristine CA (PCA). The hesperidin incorporated CA gels were found to show the best adsorption condition at neutral pH and an optimum contact time of 2.5h at 25°C. Considering the possibility of ingested Hg detoxification from human alimentary tract, the hesperidin and morin incorporated CA beads were further modified through incorporation of cod liver oil as the digestion time of fat in stomach is higher. In vitro uptake capacities of Hg in pepsin and pancreatin containing enzyme media were studied with hesperidin and morin incorporated beads and their corresponding fat incorporated beads also. In the pepsin medium, there was no uptake by hesperidin and fat-hesperidin incorporated beads, which is possibly due to the higher acidity of the medium. But in pancreatin medium Hg was taken up by both kinds of beads. Morin and morin-fat incorporated beads were efficient to uptake Hg from both the pepsin and pancreatin medium. The tailored CA beads may therefore serve as efficient scaffolds to rescue Hg ingested individuals. Copyright © 2016 Elsevier B.V. All rights reserved.

Secondary metabolites of ponderosa lemon (Citrus pyriformis) and their antioxidant, anti-inflammatory, and cytotoxic activities.

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Hamdan, Dalia; El-Readi, Mahmoud Zaki; Tahrani, Ahmad; Herrmann, Florian; Kaufmann, Dorothea; Farrag, Nawal; El-Shazly, Assem; Wink, Michael

2011-01-01

Column chromatography of the dichloromethane fraction from an aqueous methanolic extract of fruit peel of Citrus pyriformis Hassk. (Rutaceae) resulted in the isolation of seven compounds including one coumarin (citropten), two limonoids (limonin and deacetylnomilin), and four sterols (stigmasterol, ergosterol, sitosteryl-3-beta-D-glucoside, and sitosteryl-6'-O-acyl-3-beta-D-glucoside). From the ethyl acetate fraction naringin, hesperidin, and neohesperidin were isolated. The dichloromethane extract of the defatted seeds contained three additional compounds, nomilin, ichangin, and cholesterol. The isolated compounds were identified by MS (EI, CI, and ESI), 1H, 13C, and 2D-NMR spectral data. The limonoids were determined qualitatively by LC-ESI/MS resulting in the identification of 11 limonoid aglycones. The total methanolic extract of the peel and the petroleum ether, dichloromethane, and ethyl acetate fractions were screened for their antioxidant and anti-inflammatory activities. The ethyl acetate fraction exhibited a significant scavenging activity for DPPH free radicals (IC50 = 132.3 microg/mL). The petroleum ether fraction inhibited 5-lipoxygenase with IC50 = 30.6 microg/mL indicating potential anti-inflammatory properties. Limonin has a potent cytotoxic effect against COS7 cells [IC50 = (35.0 +/- 6.1) microM] compared with acteoside as a positive control [IC50 = (144.5 +/- 10.96) microM].

Infrared spectroscopy: a potential tool in huanglongbing and citrus variegated chlorosis diagnosis.

Science.gov (United States)

Cardinali, Marcelo Camponez do Brasil; Villas Boas, Paulino Ribeiro; Milori, Débora Marcondes Bastos Pereira; Ferreira, Ednaldo José; França e Silva, Marina; Machado, Marcos Antonio; Bellete, Barbara Sayuri; da Silva, Maria Fatima das Graças Fernandes

2012-03-15

Huanglongbing (HLB) and citrus variegated chlorosis (CVC) are serious threats to citrus production and have caused considerable economic losses worldwide, especially in Brazil, which is one of the biggest citrus producers in the world. Neither disease has a cure nor an efficient means of control. They are also generally confused with each other in the field since they share similar initial symptoms, e.g., yellowing blotchy leaves. The most efficient tool for detecting these diseases is by polymerase chain reaction (PCR). However, PCR is expensive, is not high throughput, and is subject to cross reaction and contamination. In this report, a diagnostic method is proposed for detecting HLB and CVC diseases in leaves of sweet orange trees using attenuated total reflectance Fourier transform infrared spectroscopy and the induced classifier via partial least-squares regression. Four different leaf types were considered: healthy, CVC-symptomatic, HLB-symptomatic, and HLB-asymptomatic. The results show a success rate of 93.8% in correctly identifying these different leaf types. In order to understand which compounds are responsible for the spectral differences between the leaf types, samples of carbohydrates starch, sucrose, and glucose, flavonoids hesperidin and naringin, and coumarin umbelliferone were also analyzed. The concentration of these compounds in leaves may vary due to biotic stresses. Copyright © 2012 Elsevier B.V. All rights reserved.

Enzymatic Synthesis of the Flavone Glucosides, Prunin and Isoquercetin, and the Aglycones, Naringenin and Quercetin, with Selective α-L-Rhamnosidase and β-D-Glucosidase Activities of Naringinase

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Hélder Vila-Real

2011-01-01

Full Text Available The production of flavonoid glycosides by removing rhamnose from rutinosides can be accomplished through enzymatic catalysis. Naringinase is an enzyme complex, expressing both α-L-rhamnosidase and β-D-glucosidase activities, with application in glycosides hydrolysis. To produce monoglycosylated flavonoids with naringinase, the expression of β-D-glucosidase activity is not desirable leading to the need of expensive methods for α-L-rhamnosidase purification. Therefore, the main purpose of this study was the inactivation of β-D-glucosidase activity expressed by naringinase keeping α-L-rhamnosidase with a high retention activity. Response surface methodology (RSM was used to evaluate the effects of temperature and pH on β-D-glucosidase inactivation. A selective inactivation of β-D-glucosidase activity of naringinase was achieved at 81.5∘C and pH 3.9, keeping a very high residual activity of α-L-rhamnosidase (78%. This was a crucial achievement towards an easy and cheap production method of very expensive flavonoids, like prunin and isoquercetin starting from naringin and rutin, respectively.

Citrus flavanones prevent systemic inflammation and ameliorate oxidative stress in C57BL/6J mice fed high-fat diet.

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Ferreira, Paula S; Spolidorio, Luis C; Manthey, John A; Cesar, Thais B

2016-06-15

The flavanones hesperidin, eriocitrin and eriodictyol were investigated for their prevention of the oxidative stress and systemic inflammation caused by high-fat diet in C57BL/6J mice. The mice received a standard diet (9.5% kcal from fat), high-fat diet (45% kcal from fat) or high-fat diet supplemented with hesperidin, eriocitrin or eriodictyol for a period of four weeks. Hesperidin, eriocitrin and eriodictyol increased the serum total antioxidant capacity, and restrained the elevation of interleukin-6 (IL-6), macrophage chemoattractant protein-1 (MCP-1), and C-reactive protein (hs-CRP). In addition, the liver TBARS levels and spleen mass (g per kg body weight) were lower for the flavanone-treated mice than in the unsupplemented mice. Eriocitrin and eriodictyol reduced TBARS levels in the blood serum, and hesperidin and eriodictyol also reduced fat accumulation and liver damage. The results showed that hesperidin, eriocitrin and eriodictyol had protective effects against inflammation and oxidative stress caused by high-fat diet in mice, and may therefore prevent metabolic alterations associated with the development of cardiovascular diseases in other animals.

Flavonoids from the Leaves of Impatiens bicolor

OpenAIRE

TAHIR, Aurangzeb HASAN and Muhammad Nawaz

2005-01-01

Three new flavanone glycosides, naringenin 4'-O-b-D-glucuronopyranoside, naringenin 4'-O-a-L rham\\-nopyranoside and naringenin 4'-O-b-D-xylopyranoside, were characterized from the leaves of Impatiens bicolor, together with 6 known glycosides: naringenin 4'-O-b-D-glucopyranoside, kaempferol 7-O-b-D-glucuronopyranoside, quercetin 3-O-b-D-glucopyranoside, kaempferol 5-O-b-D-xylopyranoside, kaempferol 3-O-b-D-galactopyranoside and kaempferol 7-O-b-D-xylopyranoside. The...

Flavonoids from the Leaves of Impatiens bicolor

OpenAIRE

TAHIR, Aurangzeb HASAN and Muhammad Nawaz; HASAN, Aurangzeb

2014-01-01

Three new flavanone glycosides, naringenin 4'-O-b-D-glucuronopyranoside, naringenin 4'-O-a-L rham\\-nopyranoside and naringenin 4'-O-b-D-xylopyranoside, were characterized from the leaves of Impatiens bicolor, together with 6 known glycosides: naringenin 4'-O-b-D-glucopyranoside, kaempferol 7-O-b-D-glucuronopyranoside, quercetin 3-O-b-D-glucopyranoside, kaempferol 5-O-b-D-xylopyranoside, kaempferol 3-O-b-D-galactopyranoside and kaempferol 7-O-b-D-xylo...

Cystolithiasis in a Syrian hamster: a different outcome | Petrini ...

African Journals Online (AJOL)

Considering the positive outcome and the beneficial properties of palmitoylethanolamide, glucosamine, and hesperidin, these nutritional elements in Syrian hamsters, are recommended to reduce recurrence after surgical treatment of urolithiasis. Keywords: Glucosamine, Hamster, Hesperidin, PEA, Urolithiasis ...

Simultaneous determination of five major compounds in the traditional medicine Pyeongwee-San by high performance liquid chromatography-diode array detection and liquid chromatography-mass spectrometry/mass spectrometry.

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Lee, Bohyoung; Weon, Jin Bae; Yun, Bo-Ra; Lee, Jiwoo; Eom, Min Rye; Ma, Choong Je

2014-01-01

Pyeongwee-San (PWS) has been widely used for treating acute gastritis, chronic, and gastritis. In this paper, simultaneous determination of five compounds (naringin, hesperidin, glycyrrhizin, atractylenolide III, and magnolol) from traditional medicine PWS using the high performance liquid chromatography (HPLC) was established for quality control. Optimum separations were obtained with a SHISEIDO C18 reverse-phase column by gradient elution with 0.1% Trifluoroacetic acid (TFA) water-acetonitrile as the mobile phase. The flow rate was 1 mL/min and detection wavelength was set at 205 nm and 250 nm. Validation of the analytical method was evaluated by linearity, precision, and accuracy test. The calibration curves were linear over the established range with R (2) > 0.9978. The limit of detection (LOD) and limit of quantification (LOQ) ranged from 0.09 to 0.43 and 0.27 to 1.29 μg/mL. The method exhibited intra-day and inter-day precision range between 0.01-1.86% and 0.04-0.35% respectively. The recoveries of five compounds in PWS were in the range between 93.18-106.40%, and 0.20-1.51%. The application of this method was identified through the successful analysis of five compounds in 12 batches of PWS. In addition, identification of five compounds was confirmed by a liquid chromatography method and mass spectrometry. The HPLC method was could be accomplished to the quality control and stable experiment for the preparations consisted of five major compounds.

Finding Inhibitors of Mutant Superoxide Dismutase-1 for Amyotrophic Lateral Sclerosis Therapy from Traditional Chinese Medicine

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Hung-Jin Huang

2014-01-01

Full Text Available Superoxide dismutase type 1 (SOD1 mutations cause protein aggregation and decrease protein stability, which are linked to amyotrophic lateral sclerosis (ALS disease. This research utilizes the world’s largest traditional Chinese medicine (TCM database to search novel inhibitors of mutant SOD1, and molecular dynamics (MD simulations were used to analyze the stability of protein that interacted with docked ligands. Docking results show that hesperidin and 2,3,5,4′-tetrahydroxystilbene-2-O-β-D-glucoside (THSG have high affinity to mutant SOD1 and then dopamine. For MD simulation analysis, hesperidin and THSG displayed similar value of RMSD with dopamine, and the migration analysis reveals stable fluctuation at the end of MD simulation time. Interestingly, distance between the protein and ligand has distinct difference, and hesperidin changes the position from initial binding site to the other place. In flexibility of residues analysis, the secondary structure among all complexes does not change, indicating that the structure are not affect ligand binding. The binding poses of hesperidin and THSG are similar to dopamine after molecular simulation. Our result indicated that hesperidin and THSG might be potential lead compound to design inhibitors of mutant SOD1 for ALS therapy.

Identification of bioflavonoid as fusion inhibitor of dengue virus using molecular docking approach

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Asif Mir

Full Text Available Dengue virus with four distinct serotypes belongs to Flavivirus, poses a significant threat to human health and becomes an emerging global problem. Membrane fusion is a central molecular event during viral entry into host cell. To prevent viral infection it is necessary to interrupt the virus replication at an early stage of attachment. Dengue Virus (DENV envelope protein experiences conformational changes and it causes the virus to fuse with host cell. Hinge region movement of domain I and II in envelope protein facilitates the fusion process. Small molecules that bind in this pocket may have the ability to interrupt the conformational changes that trigger fusion process. We chose different flavonoids (baicalein, fisetin, hesperetin, naringenin/ naringin, quercetin and rutin that possess anti dengue activity. Molecular docking analysis was done to examine the inhibitory effect of flavonoids against envelope protein of DENV-2. Results manifest quercetin (flavonoid found in Carica papaya, apple and even in lemon as the only flavone that can interrupt the fusion process of virus by inhibiting the hinge region movement and by blocking the conformational rearrangement in envelope protein. These novel findings using computational approach are worthwhile and will be a bridge to check the efficacy of compounds using appropriate animal model under In vivo studies. This information can be used by new techniques and provides a way to control dengue virus infection. Keywords: Dengue virus, Inhibitor identification, Molecular docking, Interaction analysis

Divergent antiviral effects of bioflavonoids on the hepatitis C virus life cycle

Energy Technology Data Exchange (ETDEWEB)

Khachatoorian, Ronik, E-mail: RnKhch@ucla.edu [Molecular Biology Interdepartmental Ph.D. Program (MBIDP), Molecular Biology Institute, David Geffen School of Medicine at University of California, Los Angeles, California, CA (United States); Molecular Biology Institute, David Geffen School of Medicine at University of California, Los Angeles, California, CA (United States); Arumugaswami, Vaithilingaraja, E-mail: VArumugaswami@mednet.ucla.edu [Department of Molecular and Medical Pharmacology, David Geffen School of Medicine at University of California, Los Angeles, California, CA (United States); Department of Surgery, Regenerative Medicine Institute at Cedars-Sinai Medical Center, Los Angeles, California, CA (United States); Raychaudhuri, Santanu, E-mail: SRaychau@ucla.edu [Department of Microbiology, Immunology, and Molecular Genetics, David Geffen School of Medicine at University of California, Los Angeles, California, CA (United States); Yeh, George K., E-mail: GgYeh@ucla.edu [Molecular Biology Interdepartmental Ph.D. Program (MBIDP), Molecular Biology Institute, David Geffen School of Medicine at University of California, Los Angeles, California, CA (United States); Molecular Biology Institute, David Geffen School of Medicine at University of California, Los Angeles, California, CA (United States); Maloney, Eden M., E-mail: EMaloney@ucla.edu [Department of Molecular, Cell, and Developmental Biology, University of California, Los Angeles, California, CA (United States); Wang, Julie, E-mail: JulieW1521@ucla.edu [Department of Microbiology, Immunology, and Molecular Genetics, David Geffen School of Medicine at University of California, Los Angeles, California, CA (United States); and others

2012-11-25

We have previously demonstrated that quercetin, a bioflavonoid, blocks hepatitis C virus (HCV) proliferation by inhibiting NS5A-driven internal ribosomal entry site (IRES)-mediated translation of the viral genome. Here, we investigate the mechanisms of antiviral activity of quercetin and six additional bioflavonoids. We demonstrate that catechin, naringenin, and quercetin possess significant antiviral activity, with no associated cytotoxicity. Infectious virion secretion was not significantly altered by these bioflavonoids. Catechin and naringenin demonstrated stronger inhibition of infectious virion assembly compared to quercetin. Quercetin markedly blocked viral translation whereas catechin and naringenin demonstrated mild activity. Similarly quercetin completely blocked NS5A-augmented IRES-mediated translation in an IRES reporter assay, whereas catechin and naringenin had only a mild effect. Moreover, quercetin differentially inhibited HSP70 induction compared to catechin and naringenin. Thus, the antiviral activity of these bioflavonoids is mediated through different mechanisms. Therefore combination of these bioflavonoids may act synergistically against HCV.

Nutritional Programming of Bone Structure in Male Offspring by Maternal Consumption of Citrus Flavanones.

Science.gov (United States)

Sacco, Sandra M; Saint, Caitlin; LeBlanc, Paul J; Ward, Wendy E

2018-06-01

Maternal exposure to hesperidin (HSP) and naringin (NAR) during pregnancy and lactation transiently compromised bone mineral density (BMD) and bone structure at the proximal tibia in female CD-1 offspring. We examined whether maternal consumption of HSP + NAR during pregnancy and lactation compromises BMD, bone structure, and bone strength in male CD-1 offspring. Male CD-1 offspring, from mothers fed a control diet (CON, n = 10) or a 0.5% HSP + 0.25% NAR diet (HSP + NAR, n = 8) for 5 weeks before mating and throughout pregnancy and lactation, were weaned and fed CON until 6 months of age. In vivo micro-computed tomography (µCT) measured tibia BMD and structure at 2, 4, and 6 months of age. Ex vivo µCT measured femur and lumbar vertebrae (LV) structure at age 6 months. Ex vivo BMD (femur, LV) and biomechanical strength (femur and tibia midpoint, femur neck) were assessed at age 6 months by dual energy x-ray absorptiometry and strength testing, respectively. At all ages, HSP + NAR offspring had greater (p structure compared to CON offspring. At age 4 months, proximal tibia trabecular structure was greater (p structure were greater (p structure at the proximal tibia in male CD-1 offspring that persisted to 6 months of age. Thus, maternal programming of offspring BMD and bone structure from consumption of HSP + NAR occurred as a sex-specific response.

Access to the substituted benzyl-1,2,3-triazolyl hesperetin derivatives expressing antioxidant and anticancer effects

Czech Academy of Sciences Publication Activity Database

Mistry, B.; Patel, Rahul V.; Keum, Y.S.

2017-01-01

Roč. 10, č. 2 (2017), s. 157-166 ISSN 1878-5352 R&D Projects: GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : free-radical method * oxidative stress * hesperidin * prevention * diseases * Hesperidin * Hesperetin * Cycloaddition * Click chemistry * Anticancer * Antioxidant Subject RIV: EB - Genetics ; Molecular Biology OBOR OECD: Oncology Impact factor: 4.553, year: 2016

Differential accumulation of flavonoids by tomato ( Solanum ...

African Journals Online (AJOL)

chalcone-hexose and quercetin-glc-rhamnose remained almost constant in the mesocarp and endocarp. The contents of eriodictyol, dicaffeoylquinic acid, naringenin and naringenin-chalcone-hexose significantly (P<0.05) increased in the epicarp ...

Inhibition of the MAPK pathway alone is insufficient to account for all of the cytotoxic effects of naringenin in MCF-7 breast cancer cells

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Lauren Eanes

2016-12-01

Full Text Available Estrogen receptor (ER antagonists such as tamoxifen (Tam have been used successfully to treat ER+ breast cancers for more than 30 years. Unfortunately, long term use of Tam can result in resistance. Tam resistance is associated with the activation of growth factor signaling pathways that promote cell proliferation and survival. The mitogen-activated protein kinase (MAPK, is up-regulated in Tam resistant (Tam-R cells. Previous studies have reported that the flavanone, naringenin (Nar can inhibit cell proliferation and induce apoptosis in ER+ breast cancer cells. Furthermore, Nar has been shown to inhibit the MAPK signaling pathways in MCF-7 cells. In this report we investigated whether inhibition of MAPK alone is mediating the effects of Nar on cell proliferation and viability. These studies will determine the mechanism of action of Nar. Tam-R MCF-7 breast cancer cells were treated with Nar or U0126, a MAPK kinase inhibitor. Our studies show that while both U0126 and Nar impaired cell proliferation and viability the combination of U0126 and Nar resulted in greater inhibition of cell viability than either compound alone. It has been previously reported that Nar can bind the ER. Our lab has also shown that Nar localizes ERα to a peri-nuclear region of the cell. Confocal microscopy revealed that in U0126 treated cells ERα displayed an even distribution across the cytoplasm as seen in untreated Tam-R cells. These studies suggest that MAPK is not the only target of Nar.

Expression of a Dianthus flavonoid glucosyltransferase in Saccharomyces cerevisiae for whole-cell biocatalysis.

Science.gov (United States)

Werner, Sean R; Morgan, John A

2009-07-15

Glycosyltransferases are promising biocatalysts for the synthesis of small molecule glycosides. In this study, Saccharomyces cerevisiae expressing a flavonoid glucosyltransferase (GT) from Dianthus caryophyllus (carnation) was investigated as a whole-cell biocatalyst. Two yeast expression systems were compared using the flavonoid naringenin as a model substrate. Under in vitro conditions, naringenin-7-O-glucoside was formed and a higher specific glucosyl transfer activity was found using a galactose inducible expression system compared to a constitutive expression system. However, S. cerevisiae expressing the GT constitutively was significantly more productive than the galactose inducible system under in vivo conditions. Interestingly, the glycosides were recovered directly from the culture broth and did not accumulate intracellularly. A previously uncharacterized naringenin glycoside formed using the D. caryophyllus GT was identified as naringenin-4'-O-glucoside. It was found that S. cerevisiae cells hydrolyze naringenin-7-O-glucoside during whole-cell biocatalysis, resulting in a low final glycoside titer. When phloretin was added as a substrate to the yeast strain expressing the GT constitutively, the natural product phlorizin was formed. This study demonstrates S. cerevisiae is a promising whole-cell biocatalyst host for the production of valuable glycosides.

Modification of membrane properties and fatty acids biosynthesis-related genes in Escherichia coli and Staphylococcus aureus: Implications for the antibacterial mechanism of naringenin.

Science.gov (United States)

Wang, Lang-Hong; Zeng, Xin-An; Wang, Man-Sheng; Brennan, Charles S; Gong, Deming

2018-02-01

In this work, modifications of cell membrane fluidity, fatty acid composition and fatty acid biosynthesis-associated genes of Escherichia coli ATCC 25922 (E. coli) and Staphylococcus aureus ATCC 6538 (S. aureus), during growth in the presence of naringenin (NAR), one of the natural antibacterial components in citrus plants, was investigated. Compared to E. coli, the growth of S. aureus was significantly inhibited by NAR in low concentrations. Combination of gas chromatography-mass spectrometry with fluorescence polarization analysis revealed that E. coli and S. aureus cells increased membrane fluidity by altering the composition of membrane fatty acids after exposure to NAR. For example, E. coli cells produced more unsaturated fatty acids (from 18.5% to 43.3%) at the expense of both cyclopropane and saturated fatty acids after growth in the concentrations of NAR from 0 to 2.20mM. For S. aureus grown with NAR at 0 to 1.47mM, the relative proportions of anteiso-branched chain fatty acids increased from 37.2% to 54.4%, whereas iso-branched and straight chain fatty acids decreased from 30.0% and 33.1% to 21.6% and 23.7%, respectively. Real time q-PCR analysis showed that NAR at higher concentrations induced a significant down-regulation of fatty acid biosynthesis-associated genes in the bacteria, with the exception of an increased expression of fabA gene. The minimum inhibitory concentration (MIC) of NAR against these two bacteria was determined, and both of bacteria underwent morphological changes after exposure to 1.0 and 2.0 MIC. Copyright © 2017 Elsevier B.V. All rights reserved.

Protective effect of naringenin in experimental ischemic stroke: down-regulated NOD2, RIP2, NF-κB, MMP-9 and up-regulated claudin-5 expression.

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Bai, Xue; Zhang, Xiangjian; Chen, Linyu; Zhang, Jian; Zhang, Lan; Zhao, Xumeng; Zhao, Ting; Zhao, Yuan

2014-08-01

Inflammatory damage plays a pivotal, mainly detrimental role in cerebral ischemic pathogenesis and may represent a promising target for treatment. Naringenin (NG) has gained growing appreciation for its beneficial biological effects through its anti-inflammatory property. Whether this protective effect applies to cerebral ischemic injury, we therefore investigate the potential neuroprotective role of NG and the underlying mechanisms. Focal cerebral ischemia in male Sprague-Dawley rats was induced by permanent middle cerebral artery occlusion (pMCAO) and NG was pre-administered intragastrically once daily for four consecutive days before surgery. Neurological deficit, brain water content and infarct volume were measured at 24 h after stroke. Immunohistochemistry, Western blot and RT-qPCR were used to explore the anti-inflammatory potential of NG in the regulation of NOD2, RIP2 and NF-κB in ischemic cerebral cortex. Additionally, the activities of MMP-9 and claudin-5 were analyzed to detect NG's influence on blood-brain barrier. Compared with pMCAO and Vehicle groups, NG noticeably improved neurological deficit, decreased infarct volume and edema at 24 h after ischemic insult. Consistent with these results, our data also indicated that NG significantly downregulated the expression of NOD2, RIP2, NF-κB and MMP-9, and upregulated the expression of claudin-5 (P < 0.05). The results provided a neuroprotective profile of NG in cerebral ischemia, this effect was likely exerted by down-regulated NOD2, RIP2, NF-κB, MMP-9 and up-regulated claudin-5 expression.

A dual character of flavonoids in influenza A virus replication and spread through modulating cell-autonomous immunity by MAPK signaling pathways

Science.gov (United States)

Dong, Wenjuan; Wei, Xiuli; Zhang, Fayun; Hao, Junfeng; Huang, Feng; Zhang, Chunling; Liang, Wei

2014-01-01

Flavonoids are well known as a large class of polyphenolic compounds, which have a variety of physiological activities, including anti-influenza virus activity. The influenza A/WSN/33 infected A549 cells have been used to screen anti-influenza virus drugs from natural flavonoid compounds library. Unexpectedly, some flavonoid compounds significantly inhibited virus replication, while the others dramatically promoted virus replication. In this study, we attempted to understand these differences between flavonoid compounds in their antivirus mechanisms. Hesperidin and kaempferol were chosen as representatives of both sides, each of which exhibited the opposite effects on influenza virus replication. Our investigation revealed that the opposite effects produced by hesperidin and kaempferol on influenza virus were due to inducing the opposite cell-autonomous immune responses by selectively modulating MAP kinase pathways: hesperidin up-regulated P38 and JNK expression and activation, thus resulting in the enhanced cell-autonomous immunity; while kaempferol dramatically down-regulated p38 and JNK expression and activation, thereby suppressing cell-autonomous immunity. In addition, hesperidin restricted RNPs export from nucleus by down-regulating ERK activation, but kaempferol promoted RNPs export by up-regulating ERK activation. Our findings demonstrate that a new generation of anti-influenza virus drugs could be developed based on selective modulation of MAP kinase pathways to stimulate cell-autonomous immunity. PMID:25429875

Cytotoxic Activities against Breast Cancer Cells of Local Justicia gendarussa Crude Extracts

Science.gov (United States)

Abd Samad, Azman; Jamil, Shajarahtunnur

2014-01-01

Justicia gendarussa methanolic leaf extracts from five different locations in the Southern region of Peninsular Malaysia and two flavonoids, kaempferol and naringenin, were tested for cytotoxic activity. Kaempferol and naringenin were two flavonoids detected in leaf extracts using gas chromatography-flame ionization detection (GC-FID). The results indicated that highest concentrations of kaempferol and naringenin were detected in leaves extracted from Mersing with 1591.80 mg/kg and 444.35 mg/kg, respectively. Positive correlations were observed between kaempferol and naringenin concentrations in all leaf extracts analysed with the Pearson method. The effects of kaempferol and naringenin from leaf extracts were examined on breast cancer cell lines (MDA-MB-231 and MDA-MB-468) using MTT assay. Leaf extract from Mersing showed high cytotoxicity against MDA-MB-468 and MDA-MB-231 with IC50 values of 23 μg/mL and 40 μg/mL, respectively, compared to other leaf extracts. Kaempferol possessed high cytotoxicity against MDA-MB-468 and MDA-MB-231 with IC50 values of 23 μg/mL and 34 μg/mL, respectively. These findings suggest that the presence of kaempferol in Mersing leaf extract contributed to high cytotoxicity of both MDA-MB-231 and MDA-MB-468 cancer cell lines. PMID:25574182

In vitro effects of myricetin, morin, apigenin, (+)-taxifolin, (+)-catechin, (−)-epicatechin, naringenin and naringin on cytochrome b5 reduction by purified NADH-cytochrome b5 reductase

International Nuclear Information System (INIS)

Çelik, Haydar; Koşar, Müberra; Arinç, Emel

2013-01-01

Highlights: • We assessed inhibitory effects of 8 dietary flavonoids on cytochrome b5 reduction by purified NADH-cytochrome b5 reductase. • The flavonol myricetin was the most potent in inhibiting cytochrome b5 reduction with an IC 50 value of 0.35 μM. • We investigated kinetics of myricetin-induced inhibition in detail. • We explored the structure–inhibitory activity relationship of compounds. • Modulation of cytochrome b5 reduction indicates a potential for myricetin to lead to some food–drug/xenobiotic interactions. - Abstract: The microsomal NADH-dependent electron transport system consisting of cytochrome b5 reductase and cytochrome b5 participates in a number of physiologically important processes including lipid metabolism as well as is involved in the metabolism of various drug and xenobiotics. In the present study, we assessed the inhibitory effects of eight dietary flavonoids representing five distinct chemical classes on cytochrome b5 reduction by purified cytochrome b5 reductase. From the flavonoids tested, myricetin was the most potent in inhibiting cytochrome b5 reduction with an IC 50 value of 0.35 μM. Myricetin inhibited b5 reductase noncompetitively with a K i of 0.21 μM with respect to cofactor NADH, and exhibited a non-linear relationship indicating non-Michaelis–Menten kinetic binding with respect to cytochrome b5. In contrast to the potent inhibitory activity of myricetin, (+)-taxifolin was found to be a weak inhibitor (IC 50 = 9.8 μM). The remaining flavonoids were inactive within the concentration range tested (1–50 μM). Analysis of structure–activity data suggested that simultaneous presence of three OH groups in ring B is a primary structural determinant for a potent enzyme inhibition. Our results suggest that inhibition of the activity of this system by myricetin or myricetin containing diets may influence the metabolism of therapeutic drugs as well as detoxification of xenobiotics

The effects of selected dietary bioflavonoid supplementation on dental caries in young rats fed a high-sucrose diet.

Science.gov (United States)

Wood, Nelson

2007-12-01

Recent evidence suggests that certain bioflavonoids reduce dental caries and cariogenic bacteria incidence. The present study evaluates two separate, but related, dietary trials -- trial 1, 0.09%, 0.18%, 0.36%, and 0.72% dietary naringenin (NAR) supplementation; and trial 2, 0.57% dietary rutin (R), quercetin (Q), and naringin (N) supplementation-on dental caries formation in 40 different male albino rats, at the expense of dextrose, for periods of 42 days. All rats were fed 40% sucrose. In dietary trial 1, rats were evaluated for dental caries, dental plaque accumulation, and saliva flow rates using oneway analysis of variance, post hoc Tukey's test, Kruskal-Wallis test, and Spearman's correlations. In dietary trial 2, rats were evaluated for occlusal dental caries only using a Kruskal-Wallis H test and analysis of variance. A 5% level of statistical significance was adopted throughout. In dietary trial 1, NAR showed a statistically significant effect on dental caries, plaque, and saliva flow rate reduction compared with the control group (P < .05-.01). An inverse dose-dependent relationship was established among the NAR experimental groups and control group. Dietary NAR supplementation significantly reduced dental caries formation, possibly because of reduced dental plaque accumulation. In dietary trial 2, statistically significant reductions in occlusal caries were observed for R, Q, and N in the maxillary molars and for Q and N in the mandibular molars compared with the control group (P < .05). Significant associations were observed among the experimental groups and maxillary (P < .05) and mandibular (P < .01) occlusal dental caries. Hence, selected bioflavonoids may show promise as an alternative means of reducing dental caries.

Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins.

Science.gov (United States)

Liu, Benguo; Li, Wei; Nguyen, Tien An; Zhao, Jian

2012-09-15

The inclusion complexation of (2-hydroxypropyl)-cyclodextrins with flavanones was investigated by phase solubility measurements, as well as thermodynamic and quantum chemical methods. Inclusion complexes were formed between (2-hydroxypropyl)-α-cyclodextrin (HP-α-CD), (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD), (2-hydroxypropyl)-γ-cyclodextrin (HP-γ-CD) and β-cyclodextrin (β-CD) and four flavanones (naringenin, naringin, hesperetin and dihydromyricetin) in aqueous solutions and their phase solubility was determined. For all the flavanones, the stability constants of their complexes formed with different CDs followed the rank order: HP-β-CD (MW 1540)>HP-β-CD (MW 1460)>HP-β-CD (MW 1380)>β-CD>HP-γ-CD>HP-α-CD. Experimental results and quantum chemical calculations showed that the ability of flavanones to form inclusion complex with (2-hydroxypropyl)-cyclodextrins was determined by both the steric effect and hydrophobicity of the flavanones. For flavanones that have similar molecular volumes, the hydrophobicity of the molecule was the main determining factor of its ability to form inclusion complexes with HP-β-CD, and the hydrophobicity parameter Log P is highly correlated with the stability constant of the complexes. Results of thermodynamic study demonstrated that hydrophobic interaction is the main driving force for the formation process of the flavanone-CD inclusion complexes. Quantum chemical analysis of the most active hydroxyl groups and HOMO (the highest occupied molecular orbital) showed that the B ring of the flavanones was most likely involved in hydrogen bonding with the side groups in the cavity of the CDs, through which the inclusion complex was stabilised. Copyright © 2012 Elsevier Ltd. All rights reserved.

Molecular docking and ADME-toxicity studies of potential compounds of medicinal plants grown in Indonesia as an anti-rheumatoid arthritis

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Awaluddin, Rizki; Muhtadi, Wildan Khairi; Chabib, Lutfi; Ikawati, Zullies; Martien, Ronny; Ismail, Hilda

2017-03-01

Rheumatoid arthritis (RA) is an autoimmune disease with recurrent bone destruction around the joints that could lead to permanent joint damage. DMARDs (Disease Modifying Anti-Rheumatoid Drugs) and NSAIDs (Non-Steroid Anti-Inflammatory Drugs) are the RA therapies with many side effects on long term use. Based on the ethnomedicine, there are many plants that could be found in Indonesia that contain the potential compounds as alternative RA therapies. The aim of this study is to assess the potential of compounds of various medicinal plants against multiple proteins that play an important role on RA through the molecular docking study and pharmacokinetic prediction. Hesperidin, EGCG (Epigallocatechin gallate), and mangiferin showed higher activity compared to the other compounds against TACE (TNF-α converting enzyme) which play an important role in the inhibition of TNF-α. Inhibition on it could suppress macrophage cell and T-cell activity by suppressing the regulation of cytokine secretion against inflammation. Furthermore, hesperidin, EGCG, and mangiferin did not show effects on CYP450 (cytochrome P450). Modification of drug delivery system must be done to increase the bioavailability of the compounds. It can be concluded that hesperidin, EGCG, and mangiferin are potential to be developed as an RA therapy with a modification of drug delivery system. This study suggest the encapsulation method using liposome as the drug carrier, which is suitable with the charactheristic of hesperidine, EGCG, and mangiferin.

[Study and comparison on HPLC fingerprints of flavonoids of frequently used Chinese materia medica in citrus].

Science.gov (United States)

Chen, Yonggang; Lin, Li

2011-10-01

To establish the HPLC fingerprint of flavonoids of the six clinical frequently used Chinese materia medica for regulating Qi flow,such as Citri grandis, C. grands, Citri Reticulatae Pericarpium, Citri Reticulatae Pericarpium Viride, Aurantii Fructus, and Aurantii Fructus Immaturus from Citrus, and analysis differences in the fingerprints to provide scientific basis for profile-effect research and clinical reasonable use. HPLC was performed on a C18 column with methanol-water (with acetic acid), to establish HPLC fingerprints of the six kinds of medicinal herbs on the same chromatograph condition. The six frequently used Chinese materia medica were divided into naringin type and hesperidin type according to the method of phytochemotaxonomy. Based on the retention time of chromatograph peaks, C. grandis and C. grands had fifteen common peaks; Citri Reticulatae Pericarpium, Citri Reticulatae Pericarpium Viride, Aurantii Fructus and Aurantii Fructus Immaturus had ten common peaks. All herbs had five common peaks. Compared with mutual model, the holistic similarity of chromatograms of C. grandis and C. grands was in the range of 0.9285 - 0.9962. The degree of similarity was high. For Citri Reticulatae Pericarpium, Citri Reticulatae Pericarpium Viride and Aurantii Fructus Immaturus, it was in the range of 0.9221 - 0.9973 and high. But the similarity of Aurantii Fructus was only in 0.4547 - 0.7733 with the mutual model. The established fingerprints of flavonoids of the six common traditional Chinese medicines can be used to compare the differences intuitively. Meanwhile, the peak height and peak areas of characteristic peaks are different remarkably, but whether it is connected with the different function of regulating Qi flow of the six medical materials in clinical use, is still needed to be studied.

Yeast Cell Factory-Platform for the Screening and the Industrial Production of Flavonoids and other Phenolic Compounds

DEFF Research Database (Denmark)

Lehka, Beata Joanna

Flavonoids are secondary plant metabolites derived from the phenylpropanoid pathway. These bioactive compounds are of great commercial interest due to their varied properties, such as anti-oxidative, anti-tumor and/or antibacterial. However, industrial production of flavonoids based on purification...... as a model for industrial production of flavonoids. By combining a balanced heterologous expression of (phenylpropanoid) naringenin biosynthetic pathway genes and the optimisation of yeast metabolism we developed a strain producing 430 mg/L of naringenin from glucose. In this set up naringenin was produced...... from Aeromonas salmonicida with relatively high activity towards tyrosine and no activity towards phenylalanine. Production of flavonoids and stilbenoids in S. cerevisiae is challenging, partially due to carbon loss towards phloretic acid by the action of an unknown endogenous reductase. Through...

Biochemical study on the effect of some antioxidants on apoptosis in irradiated male rats

International Nuclear Information System (INIS)

Abdo Kodous, A.Sh.H.

2011-01-01

Male albino rats were whole body subjected to 2 Gy every other day up to a total dose of 8 Gy. Animals sacrificed on the 8th day after irradiation showed significant decreases in testis/body weight ratio. Biochemical analysis in testicular tissues showed significant decreases in SOD and CAT activities, concomitant with significant increase in XO activity and TBARS contents. Radiation exposure induced also significant increases in testicular DNA fragmentation, significant increases in mitochondrial NO and Ca +2 contents associated with significant decrease in nuclear GSH content. Testicular LDL-C content showed a significant increase which was much higher than its increase in serum, the content of HDL-C increased significantly, contrarily to serum where a significant decrease was recorded. Histological examination through electron microscope revealed apoptosis in testicular tissue. Either allopurinol (50 mg/kg body weight supplied via intra peritoneal injection) or Hesperidine (200 mg/kg body weight supplied orally by gastric intubation) or allopurinol + hesperidine supplied to rats during 7 consecutive days before irradiation or during 7 consecutive days after irradiation resulted in significant decrease of apoptosis associated with significant amelioration in the disequilibrium between antioxidants and oxidants. All treatments have improved the biochemical alteration in testicular tissues as well as mitochondrial and nuclear changes. However, the improvement was significantly higher when allopurinol, or hesperidine or allopurinol + hesperidine were administered pre-irradiation than post-irradiation. According to the results obtained in the current study, it could be concluded that antioxidants supplementation would protect testicular tissues from apoptosis.

Mechanism of inhibition of human secretory phospholipase A2 by flavonoids: rationale for lead design

Science.gov (United States)

Lättig, Jens; Böhl, Markus; Fischer, Petra; Tischer, Sandra; Tietböhl, Claudia; Menschikowski, Mario; Gutzeit, Herwig O.; Metz, Peter; Pisabarro, M. Teresa

2007-08-01

The human secretory phospholipase A2 group IIA (PLA2-IIA) is a lipolytic enzyme. Its inhibition leads to a decrease in eicosanoids levels and, thereby, to reduced inflammation. Therefore, PLA2-IIA is of high pharmacological interest in treatment of chronic diseases such as asthma and rheumatoid arthritis. Quercetin and naringenin, amongst other flavonoids, are known for their anti-inflammatory activity by modulation of enzymes of the arachidonic acid cascade. However, the mechanism by which flavonoids inhibit Phospholipase A2 (PLA2) remained unclear so far. Flavonoids are widely produced in plant tissues and, thereby, suitable targets for pharmaceutical extractions and chemical syntheses. Our work focuses on understanding the binding modes of flavonoids to PLA2, their inhibition mechanism and the rationale to modify them to obtain potent and specific inhibitors. Our computational and experimental studies focused on a set of 24 compounds including natural flavonoids and naringenin-based derivatives. Experimental results on PLA2-inhibition showed good inhibitory activity for quercetin, kaempferol, and galangin, but relatively poor for naringenin. Several naringenin derivatives were synthesized and tested for affinity and inhibitory activity improvement. 6-(1,1-dimethylallyl)naringenin revealed comparable PLA2 inhibition to quercetin-like compounds. We characterized the binding mode of these compounds and the determinants for their affinity, selectivity, and inhibitory potency. Based on our results, we suggest C(6) as the most promising position of the flavonoid scaffold to introduce chemical modifications to improve affinity, selectivity, and inhibition of PLA2-IIA by flavonoids.

Diet, Stem Cells, and Breast Cancer Prevention

Science.gov (United States)

2011-01-01

pepper [39], flavonoids such as hesperetin and naringenin in citrus fruits and tomatoes [40], isoflavones (e.g., GEN, daidzein) from legumes and red...Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices. Nutr Cancer 1996;26:167–81. [41...38], capsaicin from chili pepper [39], flavonoids such as hesperetin and naringenin in citrus fruits and tomatoes [40], isoflavones (e.g., GEN

[Biopharmaceutics classification and absorption mechanisms primary study on four kinds of flavonoids].

Science.gov (United States)

Li, Hui-Fang; Zhang, Dong; Qu, Wen-Jun; Wang, Hai-Lin; Liu, Yang; Borjigdai, Almaz; Cui, Jian; Dong, Zheng-Qi

2016-04-01

The solubility and permeability on four kinds of flavonoids (kaempferol, hesperidin, apigenin, genistein) were test according to the theory of biopharmaceutics classification system (BCS), and their absorption mechanism. The solubility was investigated by the method in determination of solubility of "Chinese Pharmacopoeia 2010". To detect appearance permeability of compounds mentioned above, the appropriate concentrations were selected by the MTT method in cell transfer experiments in Caco-2 cell model, which established by in vitro cell culture method. Therefore, these compounds were classified with BCS according to solubility and permeability. In addition, to explore absorption mechanisms, the experiments in three different concentrations of compounds in high, medium and low in bidirectional transformation methods in Caco-2 cell model contacted. The study indicated that all of kaempferol, hesperidin, apigenin, genistein have the characteristics in low solubility and high permeability, which belong to BCSⅡ, and the absorption mechanism of kaempferol was active transportation. Whereas, hesperidin, apigenin, genistein were passive transportation. In this study, it carried out initial explorations on establishment of determination for solubility and permeability in flavonoids, and provided theoretical reference for further research on BCS in traditional Chinese medicine. Copyright© by the Chinese Pharmaceutical Association.

Bioactive components from flowers of Sambucus nigra L. increase glucose uptake in primary porcine myotube cultures and reduce fat accumulation in Caenorhabditis elegans

DEFF Research Database (Denmark)

Bhattacharya, Sumangala; Christensen, Kathrine Bisgaard; Olsen, Louise Cathrine Braun

2013-01-01

, kaempferol, ferulic acid, p-coumaric acid, and caffeic acid increased GU significantly. FAc was significantly reduced in C. elegans, when treated with elderflower extracts, their fractions and the metabolites naringenin, quercetin-3-O-rutinoside, quercetin-3-O-glucoside, quercetin-3-O-5″-acetylglycoside...... elegans. Bioassay guided chromatographic fractionations of extracts and fractions resulted in the identification of naringenin and 5-O- caffeoylquinic acid exhibiting a significant increase in GU. In addition, phenolic compounds related to those found in elderflowers were also tested, and among these...

HPLC-DAD-MS/MS profiling of phenolics from Securigera securidaca flowers and its anti-hyperglycemic and anti-hyperlipidemic activities

Directory of Open Access Journals (Sweden)

Rana M. Ibrahim

Full Text Available Abstract Securigera securidaca (L. Degen & Döefl., Fabaceae, has been widely used in the Iranian, Indian and Egyptian folk medicine as antidiabetic and anti-hyperlipidemic remedy. Phenolic profiling of the ethanolic extract (90% of the flowers of S. securidaca was performed via HPLC-DAD-MS/MS analysis in the positive and negative ion modes. The total polyphenols and flavonoids in the flowers were determined colorimetrically, and the quantification of their components was carried out using HPLC-UV. Total phenolics and flavonoids estimated as gallic acid and rutin equivalents were 82.39 ± 2.79 mg/g and 48.82 ± 1.95 mg/g of the dried powdered flowers, respectively. HPLC-DAD-MS/MS analysis of the extract allowed the identification of 39 flavonoids and eight phenolic acids. Quantitative analysis of some flavonoids and phenolics (mg/100 g powdered flowers revealed the presence of isoquercetrin (3340 ± 2.1, hesperidin (32.09 ± 2.28, naringin (197.3 ± 30.16, luteolin (10.247 ± 0.594, chlorogenic acid (84.22 ± 2.08, catechin (3.94 ± 0.57 and protocatechuic acid (34.4 ± 0.15, in the extract. Moreover, the acute toxicity, hypoglycemic and hypolipidemic effects of the extract were investigated using alloxan induced diabetes in rats in a dose of 100, 200, and 400 mg/kg bwt. The ethanolic extract was safe up to a dose of 2000 mg/kg. All tested doses of the flower extract showed marked decrease in blood glucose level by 31.78%, 66.41% and 63.8% at 100, 200 and 400 mg/kg bwt, respectively, at p < 0.05. Regarding the anti-hyperlipidemic effect, a dose of 400 mg/kg of the flower extract showed the highest reduction in serum triacylglycerides and total cholesterol levels (68.46% and 51.50%, respectively at p < 0.05. The current study proved the folk use of the flowers of S. securidaca as anti-diabetic and anti-hyperlipidemic agent which could be attributed to its high phenolic content.

Functional Foods in fad diets: A review

Directory of Open Access Journals (Sweden)

Daniela Abigail Navaro

2017-09-01

Full Text Available Background: Fad diets can be defined as any diet making claims that are unrealistic and not supported by evidence-based data. Having been developed since the early 19th century, fad diets promise drastic weight loss and/or other unsubstantiated health claims, often omitting entire food groups. Their popularity with the public makes them an important topic for nutritionists and clinicians, especially in the framework of the obesity epidemic. Additionally, it is conceivable that components of fad diets can indeed facilitate weight loss, even if the diet overall is without merit. The grapefruit diet, the cabbage soup diet, and the human chorionic gonadotropin (hCG diet are among the most popular fad diets and are reviewed within this study not only in terms of the diet plan itself, but also in terms of possible and known weight loss and health benefits provided by the foods on which the diets are based. Bioflavonoids in grapefruit, including naringin, hesperidin, and bergamottin, may benefit glucose homeostasis. Cabbage contains lutein, zeaxanthin, kaempferol, quercetin, and apigenin, which have anti-inflammatory properties and improve both glucose homeostasis and fat metabolism. The hCG diet is frequently supplemented with non-hCG preparations, which often contains African mango, which has been shown to enhance weight loss by an unspecified mechanism; astragalus root, which has antioxidant, anti-inflammatory, and peroxisome proliferator-activated receptor-gamma receptor agonistic properties; arginine, which stimulates lipolysis; glutamine, which has been shown to enhance weight loss, perhaps by altering the gut microbiome; carnitine, which appears to facilitate weight loss; B12, which improves insulin resistance; and niacin, which improves the dyslipidemia associated with overweight/obesity. Presently, high quality clinical trials suggest that fad diets reduce weight in the short term due to drastic caloric restriction rather than functional food

The permeability characteristics and interaction of main components from Si-Ni-San in a MDCK epithelial cell monolayer model.

Science.gov (United States)

Chen, Ruonan; Shen, Chenlin; Xu, Qingqing; Liu, Yaru; Li, Bo; Huang, Cheng; Ma, Taotao; Meng, Xiaoming; Wu, Maomao; Li, Jun

2017-07-26

1. Si-Ni-San (SNS) possesses extensive therapeutic effects, however, the extent to which main components are absorbed and the mechanisms involved are controversial. 2. In this study, MDCK cell model was used to determine the permeability characteristics and interaction between the major components of Si-Ni-San, including saikosaponin a, paeoniflorin, naringin and glycyrrhizic acid. 3. The transport of the major components was concentration-dependent in both directions. Moreover, the transport of paeoniflorin, naringin and glycyrrhizic acid was significantly reduced at 4°C or in the presence of NaN3. Additionally, the efflux of paeoniflorin and naringin were apparently reduced in the presence of P-gp inhibitor verapamil. The transport of glycyrrhizic acid was clearly inhibited by the inhibitors of MRP2, indicating that MRP2 may be involved in the transport of glycyrrhizic acid. However, the results indicated that saikosaponin a was absorbed mainly by passive diffusion. Furthermore, the combined incubation of four major components had a powerful sorbefacient effect than a single drug used alone which may be regulated by tight junctions. 4. Taken together, our study provides useful information for pharmacological applications of Si-Ni-San and offers new insights into this ancient decoction for further researches, especially in drug synergism.

Analysis of the relationship between Chalcone Isomerase gene expression level and rutin production in Ficus deltoidea var. deltoidea and F. deltoidea var. angustifolia

Science.gov (United States)

Najid, Najihah Mohd; Zain, Che Radziah Che Mohd; Zainal, Zamri

2016-11-01

Ficus deltoidea (moraceae) is a herbal plant with medicinal values. Previous studies reported that the F. deltoidea contains a high level of bioactive compounds such as flavonoids. A cDNA encodes for chalcone isomerase was identified from F. deltoidea, designated as FdCHI, which involved in the isomerization of naringenin chalcone to naringenin. Naringenin is a key branch point for the synthesis of rutin, which is believed involved in defense mechanism in the plant. Therefore, we hypothesized that there might be a direct relationship between FdCHI expression level and rutin production in leaves of F. deltoidea var. deltoidea (FDD) and F. deltoidea var. angustifolia (FDA). Our result showed that expression level of FdCHI in leaves FDD was greater than FDA. Analysis of High Performance Liquid Chromatography (HPLC) revealed that rutin was only detected in FDA leaves. Based on the results between FdCHI expression and rutin production, this study concluded that there is no relationship between FdCHI expression and rutin production in leaves of FDA and FDD.

Anticarcinogenic compounds in the Uzbek medicinal plant, Helichrysum maracandicum.

Science.gov (United States)

Yagura, Toru; Motomiya, Tomoko; Ito, Michiho; Honda, Gisho; Iida, Akira; Kiuchi, Fumiyuki; Tokuda, Harukuni; Nishino, Hoyoku

2008-04-01

An ethanol extract of Helichrysum maracandicum showed antiproliferative activity against cultured cells of SENCAR mouse in an in vitro assay, and activity-guided fractionation of the extract resulted in the isolation of isosalipurposide as an active substance. Naringenin chalcone, the aglycone of isosalipurposide, also showed strong antiproliferative activity. An in vivo assay of two-stage carcinogenesis on mouse skin revealed that epidermal application of isosalipurposide resulted in delayed formation of papillomas. Western blot analysis showed that the expression of p38 mitogen-activated protein kinase was suppressed by the administration of naringenin chalcone or isosalipurposide, which might be related to the anticarcinogenic activity.

Beneficial effects of hesperidin following cis ...

African Journals Online (AJOL)

lower in this group. On the other .... at an ambient temperature of 21°C. Diet and water for them were given .... findings of the present study, HP protects heart muscle cells ... protein synthesis, and causes apoptosis after mitochondrial damage.

Quality evaluation of Poza bitters, a new poly herbal formulation in ...

African Journals Online (AJOL)

70:5) showed three spots with Rf values similar to some of references used. High performance liquid chromatography fingerprint showed two retention times of poza bitters which were not similar to those of the reference standards: hesperidin ...

Influence of l -rhamnosyl-d -glucosyl derivatives on properties and biological interaction of flavonoids

Czech Academy of Sciences Publication Activity Database

Bellocco, E.; Barreca, D.; Lagana, G.; Leuzzi, U.; Tellone, E.; Ficarra, S.; Kotyk, Arnošt; Galtieri, A.

2009-01-01

Roč. 321, 1-2 (2009), s. 165-171 ISSN 0300-8177 Institutional research plan: CEZ:AV0Z50110509 Keywords : hesperidin * hesperetin * anti-proliferative activity * apoptotic pathway Subject RIV: ED - Physiology Impact factor: 1.896, year: 2009

Catabolism of citrus flavanones by the probiotics Bifidobacterium longum and Lactobacillus rhamnosus.

Science.gov (United States)

Pereira-Caro, Gema; Fernández-Quirós, Begoña; Ludwig, Iziar A; Pradas, Inmaculada; Crozier, Alan; Moreno-Rojas, José Manuel

2018-02-01

Orange juice (OJ) flavanones undergo limited absorption in the upper gastrointestinal tract and reach the colon where they are transformed by the microbiota prior to absorption. This study investigated the ability of two probiotic bacteria, Bifidobacterium longum R0175 and Lactobacillus rhamnosus subsp. Rhamnosus NCTC 10302 to catabolise OJ flavanones. The bacteria were incubated with hesperetin-7-O-rutinoside, naringenin-7-O-rutinoside, hesperetin and naringenin, and the culture medium and intracellular cell extracts were collected at intervals over a 48 h of incubation period. The flavanones and their phenolic acid catabolites were identified and quantified by HPLC-HR-MS. Both probiotics were able to subject hesperetin to ring fission yielding 3-(3'-hydroxy-4'-methoxyphenyl)propionic acid which was subsequently demethylated producing 3-(3',4'-dihydroxyphenyl)propionic acid and then via successive dehydroxylations converted to 3-(3'-hydroxyphenyl)propionic acid and 3-(phenyl)propionic acid. Incubation of both bacteria with naringenin resulted in its conversion to 3-(4'-hydroxyphenyl)propionic acid which underwent dehydroxylation yielding 3-(phenyl)propionic acid. In addition, only L. rhamnosus exhibited rhamnosidase and glucosidase activity and unlike B. longum, which was able to convert hesperetin-7-O-rutinoside and naringenin-7-O-rutinoside to their respective aglycones. The aglycones were then subjected to ring fission and further catabolised in a similar manner to that described above. The flavanones and their catabolites were found in the culture medium but not accumulated in the bacterial cells. These findings demonstrate the enzymatic potential of single strains of bifidobacterium and lactobacillus which may be involved in the colonic catabolism of OJ flavanones in vivo.

Anticarcinogenic Effect of Spices Due to Phenolic and Flavonoid Compounds-In Vitro Evaluation on Prostate Cells.

Science.gov (United States)

Lackova, Zuzana; Buchtelova, Hana; Buchtova, Zaneta; Klejdus, Borivoj; Heger, Zbynek; Brtnicky, Martin; Kynicky, Jindrich; Zitka, Ondrej; Adam, Vojtech

2017-09-28

This study shows the effects of spices, and their phenolic and flavonoid compounds, on prostate cell lines (PNT1A, 22RV1 and PC3). The results of an MTT assay on extracts from eight spices revealed the strongest inhibitory effects were from black pepper and caraway seed extracts. The strongest inhibitory effect on prostatic cells was observed after the application of extracts of spices in concentration of 12.5 mg·mL -1 . An LC/MS analysis identified that the most abundant phenolic and flavonoid compounds in black pepper are 3,4-dihydroxybenzaldehyde and naringenin chalcone, while the most abundant phenolic and flavonoid compounds in caraway seeds are neochlorogenic acid and apigenin. Using an MTT assay for the phenolic and flavonoid compounds from spices, we identified the IC 50 value of ~1 mmol·L -1 PNT1A. The scratch test demonstrated that the most potent inhibitory effect on PNT1A, 22RV1 and PC3 cells is from the naringenin chalcone contained in black pepper. From the spectrum of compounds assessed, the naringenin chalcone contained in black pepper was identified as the most potent inhibitor of the growth of prostate cells.

Sadhana | Indian Academy of Sciences

Indian Academy of Sciences (India)

desorption technique using an indigenous resin · M LAXMI DEEPAK BHATLU SATYA VIR SINGH ASHOK KUMAR VERMA · More Details Abstract Fulltext PDF. A process technology has been developed for recovery of naringin from kinnow ...

Effects of Drying Temperature on Flavonoids Extraction Rate from Young Stems and Leaves of Two Cassava Varieties

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WANG Ding-mei

2017-01-01

Full Text Available To improve flavonoids resources utilization level of young cassava stems and leaves, using cassava varieties SC09 and SC205 as ob jects, investigated the effect of different drying temperatures(40~120℃on the flavonoids extraction rate(FERand their stability in 120 d storage period after drying, explored a right drying storage method for postharvest young cassava stems and leaves. The research showed that total FER rised first, and then fell and rised again with the increase of drying temperature. During 40~80℃, the total FER was obviously in fluenced by variety and temperature, but only temperature was main factor affecting total FER during 90~120℃. Extract degree of flavonoids include rutin, amentoflavone or catechin, kaempferol, hesperidin, quercetin minished in order; the effect of cassava variety on the extraction rate of catechin and hesperidin was greater than that of drying temperature, but that contrary to other 4 flavonoids. Variety and temperature had a maximum impact respectively on catechin and rutin extraction rates. Whereas both of variety and temperature had a minimum impact on kaempferol extraction rate. FER reached higher levels of 1.42%and 1.53% respectively in SC09 after 120℃drying and SC205 after 110℃drying, and had best stability during 120 d storage period. The extraction rate of hesperidin increased after drying storage, and that of other 5 ingredients were changing with different varieties and temperatures; the coefficient variation(CV=1.03%~6.86%of kaempferol was minimum and its stability was best; extraction rates of rutin and kaempferol in SC205 after 110℃drying were maximum, whose increasing rates were 44.89%and 7.27%respectively with a small separate degree(CV were 6.94%, 4.59%and good extraction stability. Maximum in creasing rates of catechin, amentoflavone, quercetin and hesperidin were 211.60%，17.60%，186.39% and 538.08% respectively. However,their stabilities of extraction efficiency were poor

Cystolithiasis in a Syrian hamster: a different outcome

Directory of Open Access Journals (Sweden)

D. Petrini

2016-08-01

Full Text Available A 14-month-old intact male Syrian hamster was admitted for lethargy and hematuria. A total body radiographic image and abdominal ultrasonography showed the presence of a vesical calculus. During cystotomy, a sterile urine sample was obtained and sent to the diagnostic laboratory along with the urolith for analysis. Urine culture was found negative for bacterial growth, and the urolith was identified as a calcium-oxalate stone. Diet supplementation with palmitoylethanolamide, glucosamine and hesperidin was adopted the day after discharge. One year follow up revealed no presence of vesical calculi. Although this is the report of a single clinical case, this outcome differs from the results reported in the literature characterized by recurrences after few months. Considering the positive outcome and the beneficial properties of palmitoylethanolamide, glucosamine, and hesperidin, these nutritional elements in Syrian hamsters, are recommended to reduce recurrence after surgical treatment of urolithiasis.

THE X-RAY STRUCTURE AND THE 13 C NMR DATA OF ...

African Journals Online (AJOL)

The alkaloids pellitorine and chelerythrine acetonate were isolated from the stem bark of Zanthoxylum davyi together with methyl octadecyl ketone, lupeol and hesperidin. The alkaloid skimmianie was isolated from the leaves. The X-Ray structure of chelerythrine acetonate was also determined. Key Words: Zanthoxylum ...

Pathway Analysis and Metabolites Identification by Metabolomics of Etiolation Substrate from Fresh-Cut Chinese Water Chestnut (Eleocharis tuberosa

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Yi-Xiao Li

2016-12-01

Full Text Available Fresh-cut Chinese water chestnuts (CWC turn yellow after being peeled, reducing their shelf life and commercial value. Metabolomics, the systematic study of the full complement of small molecular metabolites, was useful for clarifying the mechanism of fresh-cut CWC etiolation and developing methods to inhibit yellowing. In this study, metabolic alterations associated with etiolation at different growth stages (0 day, 2 days, 3 days, 4 days, 5 days from fresh-cut CWC were investigated using LC–MS and analyzed by pattern recognition methods (principal component analysis (PCA, partial least squares-discriminant analysis (PLS-DA, and orthogonal projection to latent structures-discriminant analysis (OPLS-DA. The metabolic pathways of the etiolation molecules were elucidated. The main metabolic pathway appears to be the conversion of phenylalanine to p-coumaroyl-CoA, followed by conversion to naringenin chalcone, to naringenin, and naringenin then following different pathways. Firstly, it can transform into apigenin and its derivatives; secondly, it can produce eriodictyol and its derivatives; and thirdly it can produce dihydrokaempferol, quercetin, and myricetin. The eriodictyol can be further transformed to luteolin, cyanidin, dihydroquercetin, dihydrotricetin, and others. This is the first reported use of metabolomics to study the metabolic pathways of the etiolation of fresh-cut CWC.

Phytochemical study from root barks of Zanthoxylum rigidum Humb. and Bonpl. ex Willd (Rutaceae)

International Nuclear Information System (INIS)

Moccelini, Sally Katiuce; Silva, Virginia Claudia da; Ndiaye, Eliane Augusto; Sousa Junior, Paulo Teixeira de; Vieira, Paulo Cezar

2009-01-01

Chemical investigation from root barks of Z. rigidum, resulted in the isolation of lupeol, a mixture of steroids campesterol, sitosterol, stigmasterol, sacarose, hesperidin, N-methylatanine and 6-acetonyldihydrochelerythrine. Their structures were established by spectral data analysis. No previous work has been reported on Z. rigidum species. (author)

Phytochemical study from root barks of Zanthoxylum rigidum Humb. and Bonpl. ex Willd (Rutaceae); Estudo fitoquimico das cascas das raizes de Zanthoxylum rigidum Humb. and Bonpl. ex Willd (Rutaceae)

Energy Technology Data Exchange (ETDEWEB)

Moccelini, Sally Katiuce; Silva, Virginia Claudia da; Ndiaye, Eliane Augusto; Sousa Junior, Paulo Teixeira de [Universidade Federal de Mato Grosso (UFMT), Cuiaba, MT(brazil). Dept. de Quimica; Vieira, Paulo Cezar [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica]. E-mail: teixeira@ufmt.br

2009-07-01

Chemical investigation from root barks of Z. rigidum, resulted in the isolation of lupeol, a mixture of steroids campesterol, sitosterol, stigmasterol, sacarose, hesperidin, N-methylatanine and 6-acetonyldihydrochelerythrine. Their structures were established by spectral data analysis. No previous work has been reported on Z. rigidum species. (author)

Cytotoxic, genotoxic and apoptotic effects of naringenin-oxime relative to naringenin on normal and cancer cell lines

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Abdurrahim Kocyigit

2016-10-01

Conclusions: This study showed that both NG-Ox and NG possess cytotoxic, genotoxic and apoptotic activities through the production of ROS on cells, NG-Ox being the more effective one. Therefore, derived compound of NG might be used as antiproliferative agents for the treatment of cancer.

Simultaneous kinetic spectrometric determination of three flavonoid antioxidants in fruit with the aid of chemometrics

Science.gov (United States)

Sun, Ruiling; Wang, Yong; Ni, Yongnian; Kokot, Serge

2014-03-01

A simple, inexpensive and sensitive kinetic spectrophotometric method was developed for the simultaneous determination of three anti-carcinogenic flavonoids: catechin, quercetin and naringenin, in fruit samples. A yellow chelate product was produced in the presence neocuproine and Cu(I) - a reduction product of the reaction between the flavonoids with Cu(II), and this enabled the quantitative measurements with UV-vis spectrophotometry. The overlapping spectra obtained, were resolved with chemometrics calibration models, and the best performing method was the fast independent component analysis (fast-ICA/PCR (Principal component regression)); the limits of detection were 0.075, 0.057 and 0.063 mg L-1 for catechin, quercetin and naringenin, respectively. The novel method was found to outperform significantly the common HPLC procedure.

Purification and characterization of two different a-L-Rhamnosidases, RhaA and RhaB, from Aspergillus aculeatus

NARCIS (Netherlands)

Manzanares, P.; Broeck, H.C.; Graaff, de L.H.; Visser, J.

2001-01-01

Two proteins exhibiting -L-rhamnosidase activity, RhaA and RhaB, were identified upon fractionation and purification of a culture filtrate from Aspergillus aculeatus grown on hesperidin. Both proteins were shown to be N glycosylated and had molecular masses of 92 and 85 kDa, of which approximately

Fresh and Commercially Pasteurized Orange Juice: An Analysis of the Metabolism of Flavonoid Compounds

Science.gov (United States)

Orange juice is a rich source of flavonoids, mainly the flavanones hesperidin and narirutin, associated with health benefits in humans. The objective of this study was to analyze the uptake of flavonoids in humans after the consumption of two types of orange juice, fresh squeezed (fresh juice, FJ) a...

Flavonoid, hesperidine, total phenolic contents and antioxidant ...

African Journals Online (AJOL)

ONOS

2010-01-11

Jan 11, 2010 ... from citrus were mainly focused on its essential oils which include ... High performance liquid chromatography coupled to diode array detector ..... properties of xanthin on autoxidation of soybean oil in cyclodextrin emulsion.

Antioxidant activities and radical scavenging activities of flavonoids studied by the electrochemical methods and ESR technique based on the novel paramagnetic properties of poly(aniline-co-5-aminosalicylic acid)

International Nuclear Information System (INIS)

Yang, Yifei; Mu, Shaolin

2013-01-01

Graphical abstract: ESR spectra of the PAASA/RGO/graphite electrodes: (1) in the buffer solution consisting of 0.20 M phosphate and methanol (80: 20, v/v), (2) in the buffer solutions containing 150 μM of (+)-catechin. -- Abstract: Four kinds of flavonoid, viz. flavanone naringenin, Flavone apigenin, flavonol kaempferol, and flavanol (+)-catechin, are used to investigate their antioxidant and radical scavenging activitis in the water-methanol solution of pH 6.3, using the electrochemical methods and electron spin resonance (ESR) technique. Poly(aniline-co-5-aminosalicylic acid) (PAASA) is first used as a radical source that was polymerized on a reduced graphene oxide (RGO)/glassy carbon (GC) disk or on the RGO/graphite fiber electrode. The assessment of the antioxidant activities is performed using both cyclic voltammetry and the open circuit potential measurement. On the basis of results from both electrochemical mathods, the order of the antioxidant actitvities of flavonoids is as follows: (+)-catechin > kaempferol > apigenin > naringenin However, the difference in the antioxidant activities between naringenin and apigenin is very small. On the basis of the ESR signal intensities of PAASA, the order of the radical scavenging activities of flavonoids is in good agreement with that of the above antioxdant activities.Three oxidation peaks on the cyclic voltammograms of (+)-catechin are first detected, which gives us a deep insight into the oxidation mechanism of (+)-catechin

Differential accumulation of flavonoids by tomato (Solanum ...

African Journals Online (AJOL)

SARAH

2014-12-29

Dec 29, 2014 ... Objective: Little is known about physiological functions of flavonoids, specifically in the course of maturation ... epicarp (especially naringenin) with the onset of the ripening. ..... the University of Chemical Technology and.

Transcriptome Profiling of Tomato Uncovers an Involvement of Cytochrome P450s and Peroxidases in Stigma Color Formation

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Yan Zhang

2017-05-01

Full Text Available Stigma is a crucial structure of female reproductive organ in plants. Stigma color is usually regarded as an important trait in variety identification in some species, but the molecular mechanism of stigma color formation remains elusive. Here, we characterized a tomato mutant, yellow stigma (ys, that shows yellow rather than typical green color in the stigma. Analysis of pigment contents revealed that the level of flavonoid naringenin chalcone was increased in the ys stigma, possibly as a result of higher accumulation of p-coumaric acid, suggesting that naringenin chalcone might play a vital role in yellow color control in tomato stigma. To understand the genes and gene networks that regulate tomato stigma color, RNA-sequencing (RNA-Seq analyses were performed to compare the transcriptomes of stigmas between ys mutant and wild-type (WT. We obtained 507 differentially expressed genes, in which, 84 and 423 genes were significantly up-regulated and down-regulated in the ys mutant, respectively. Two cytochrome P450 genes, SlC3H1 and SlC3H2 which encode p-coumarate 3-hydroxylases, and six peroxidase genes were identified to be dramatically inhibited in the yellow stigma. Further bioinformatic and biochemical analyses implied that the repression of the two SlC3Hs and six PODs may indirectly lead to higher naringenin chalcone level through inhibiting lignin biosynthesis, thereby contributing to yellow coloration in tomato stigma. Thus, our data suggest that two SlC3Hs and six PODs are involved in yellow stigma formation. This study provides valuable information for dissecting the molecular mechanism of stigma color control in tomato.Statement: This study reveals that two cytochrome P450s (SlC3H1 and SlC3H2 and six peroxidases potentially regulate the yellow stigma formation by indirectly enhancing biosynthesis of yellow-colored naringenin chalcone in the stigma of tomato.

Synthesis of fisetin and 2',4',6'-trihydroxydihyrochalcone 4'-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation.

Science.gov (United States)

Tsunekawa, Ryuji; Hanaya, Kengo; Higashibayashi, Shuhei; Sugai, Takeshi

2018-04-26

Fisetin and 2',4',6'-trihydroxydihyrochalcone 4'-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.

Optimizing culture medium for debittering constitutive enzyme ...

African Journals Online (AJOL)

The objective of this study was to investigate nutrient requirements for extracellular constitutive naringinase production by Aspergillus oryzae JMU316. The one-factor-at-a-time method was used to determine the impact of different carbon and nitrogen sources on naringinase production. Naringin exhibited the highest ...

A process to preserve valuable compounds and acquire essential oils from pomelo flavedo using a microwave irradiation treatment.

Science.gov (United States)

Liu, Zaizhi; Zu, Yuangang; Yang, Lei

2017-06-01

A microwave pretreatment method was developed to preserve pectin, naringin, and limonin contents in pomelo flavedo to allow for longer storage times and subsequent extraction of pomelo essential oil. In terms of the essential oil, microwave pretreatment performed better than hydrodistillation with respect to extraction efficiency (1.88±0.06% in 24min versus 1.91±0.08% in 240min), oxygenation fraction (48.59±1.32% versus 29.63±1.02%), energy consumption (0.15kWh versus 1.54kWh), and environmental impact (123.20g CO 2 versus 1232g CO 2 ). Microwave-pretreated samples retained higher amounts of pectin, naringin, and limonin compared with non-pretreated samples. No obvious change in the degree of pectin esterification was observed. This study shows that the proposed process is a promising methodology for both preserving valuable compounds in pomelo flavedo during storage and acquiring essential oils. Copyright © 2016 Elsevier Ltd. All rights reserved.

Starch digestibility and predicted glycemic index in the bread fortified with pomelo (Citrus maxima) fruit segments.

Science.gov (United States)

Reshmi, S K; Sudha, M L; Shashirekha, M N

2017-12-15

The aim of this study was to evaluate the starch digestibility and predicted glycemic index in breads incorporated with pomelo fruit (Citrus maxima) segments. Volume of the white and brown breads supplemented with pomelo fresh segments increased, while the crumb firmness decreased. Bread with 20% fresh and 5% dry pomelo segments were sensorily acceptable. Bioactive components such as phenolics, flavonoids, naringin and carotenoids were retained to a greater extent in bread containing dry pomelo segments. The pomelo incorporated bread had higher levels of resistant starch fractions (3.87-10.96%) with low predicted glycemic index (62.97-53.13%), despite their higher total starch (69.87-75.47%) content compared to control bread. Thus pomelo segments in the product formulations lowered the glycemic index probably by inhibiting carbohydrate hydrolyzing enzyme activity which could be attributed to naringin. Hence fortified bread prepared from pomelo fruit segment is recommended to gain nutritional value and to decrease the risk of diabetes. Copyright © 2017 Elsevier Ltd. All rights reserved.

[Advance in flavonoids biosynthetic pathway and synthetic biology].

Science.gov (United States)

Zou, Li-Qiu; Wang, Cai-Xia; Kuang, Xue-Jun; Li, Ying; Sun, Chao

2016-11-01

Flavonoids are the valuable components in medicinal plants, which possess a variety of pharmacological activities, including anti-tumor, antioxidant and anti-inflammatory activities. There is an unambiguous understanding about flavonoids biosynthetic pathway, that is,2S-flavanones including naringenin and pinocembrin are the skeleton of other flavonoids and they can transform to other flavonoids through branched metabolic pathway. Elucidation of the flavonoids biosynthetic pathway lays a solid foundation for their synthetic biology. A few flavonoids have been produced in Escherichia coli or yeast with synthetic biological technologies, such as naringenin, pinocembrin and fisetin. Synthetic biology will provide a new way to get valuable flavonoids and promote the research and development of flavonoid drugs and health products, making flavonoids play more important roles in human diet and health. Copyright© by the Chinese Pharmaceutical Association.

Characteristics of chalcone isomerase promoter in crabapple leaves ...

African Journals Online (AJOL)

Administrator

2011-09-05

Sep 5, 2011 ... in flavonoid biosynthetic pathway, can convert chalcone to (2S)-naringenin in the ... Construction of expression vectors with McCHI promoter fragment ... Each sample was bombarded three times with tungsten particles coated ...

Dietary nutraceuticals as novel radioprotectors

International Nuclear Information System (INIS)

Jagetia, Ganesh Chandra

2012-01-01

There is long standing need to protect humans from the deleterious effects of ionizing radiation in the event of radiation related calamities or otherwise. Various dietary ingredients have formed an integral part of daily human diets. Most of the ingredients used in the Indian diet possess medicinal properties. However, little attention has been paid to screen the radioprotective ability of dietary ingredients. It is possible that use of dietary agents could protect against the deleterious effects of ionizing radiations more effectively than other exotic synthetic agents simply because they are from natural biological sources, and may be more biocompatible than any other synthetic counterparts. Their acceptance for therapeutic purpose will be acceptable as they are part of daily human diets and do not have any known toxicity. This has been a stimulation to investigate the radioprotective ability of certain dietary ingredients including naringin and mangiferin in vivo and in vitro using micronuclei or survival assays. Treatment of mice with various doses of naringin or mangiferin reduced the symptoms of radiation-induced sickness including listlessness, irritability, lethargy, reduction in food and water intake, diarrhea, lacrimation, facial edema weight loss, emaciation, and epilation. Mice receiving various doses of naringin reduced the radiation-induced micronuclei formation and chromosome aberrations in bone marrow. Likewise, treatment of human peripheral blood lymphocytes with various concentrations of mangiferin reduced the radiation-induced DNA damage. The putative mechanisms of radioprotection are free radical scavenging, increased GSH accompanied by reduced lipid peroxidation. The use of dietary ingredients for radioprotection shall be encouraged as they are consumed daily and toxic implications are negligible. (author)

Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines ( Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand.

Science.gov (United States)

Stuetz, Wolfgang; Prapamontol, Tippawan; Hongsibsong, Surat; Biesalski, Hans-Konrad

2010-05-26

Polymethoxylated flavones (PMFs) and flavanone glycosides (FGs) were analyzed in hand-pressed juice and the peeled fruit of 'Sainampueng' tangerines ( Citrus reticulata Blanco cv. Sainampueng) grown in northern Thailand. The tangerines were collected from a citrus cluster of small orchard farmers and were cultivated as either agrochemical-based (AB), agrochemical-safe (AS), or organic grown fruits. Juice samples were also measured on contents of carotenoids, ascorbic acid, and tocopherols. The peel-deriving PMFs tangeretin, nobiletin, and sinensetin were found with high concentrations in juice as a result of simple squeezing, whereas amounts of those PMFs were negligibly low in peeled tangerine fruit. In contrast, the mean concentrations of the FGs narirutin, hesperidin, and didymin were several fold higher in peeled fruit than in tangerine juice and significantly higher in organic than AS and AB tangerines. Narirutin and hesperidin in juice from organic produces as well as narirutin in juice from AS produces were significantly higher than respective mean concentrations in juice from AB produces. beta-Cryptroxanthin was the predominant carotenoid beside zeaxanthin, lutein, lycopene, and beta-carotene in tangerine juice. Ascorbic acid concentrations were not predicted by the type of cultivation, whereas alpha-tocopherol was significantly higher in juice from organic than AS produces. In summary, hand-pressed juice of C. reticulata Blanco cv. Sainampueng serves as a rich source of PMFs, FGs, carotenoids, and antioxidants: 4-5 tangerine fruits ( approximately 80 g of each fruit) giving one glass of 200 mL hand-pressed juice would provide more than 5 mg of nobiletin and tangeretin and 36 mg of hesperidin, narirutin, and didymin, as well as 30 mg of ascorbic acid, >1 mg of provitamin A active beta-cryptoxanthin, and 200 microg of alpha-tocopherol.

Hesperetin induces melanin production in adult human epidermal melanocytes.

Science.gov (United States)

Usach, Iris; Taléns-Visconti, Raquel; Magraner-Pardo, Lorena; Peris, José-Esteban

2015-06-01

One of the major sources of flavonoids for humans are citrus fruits, hesperidin being the predominant flavonoid. Hesperetin (HSP), the aglycon of hesperidin, has been reported to provide health benefits such as antioxidant, anti-inflammatory and anticarcinogenic effects. However, the effect of HSP on skin pigmentation is not clear. Some authors have found that HSP induces melanogenesis in murine B16-F10 melanoma cells, which, if extrapolated to in vivo conditions, might protect skin against photodamage. Since the effect of HSP on normal melanocytes could be different to that observed on melanoma cells, the described effect of HSP on murine melanoma cells has been compared to the effect obtained using normal human melanocytes. HSP concentrations of 25 and 50 µM induced melanin synthesis and tyrosinase activity in human melanocytes in a concentration-dependent manner. Compared to control melanocytes, 25 µM HSP increased melanin production and tyrosinase activity 1.4-fold (p melanin production in human melanocyte cultures could be reproduced on human skin. Copyright © 2015 Elsevier Ltd. All rights reserved.

Identifying 8-hydroxynaringenin as a suicide substrate of mushroom tyrosinase.

Science.gov (United States)

Chang, Te-Sheng; Lin, Meng-Yi; Lin, Hsuan-Jung

2010-01-01

A biotransformed metabolite of naringenin was isolated from the fermentation broth of Aspergillus oryzae, fed with naringenin, and identified as 8-hydroxynaringenin based on the mass and (1)H- and (13)C-NMR spectral data. The compound showed characteristics of both an irreversible inhibitor and a substrate of mushroom tyrosinase in preincubation and HPLC analysis. These results demonstrate that 8-hydroxynaringenin belongs to a suicide substrate of mushroom tyrosinase. The partition ratio between the compound's molecules in the formation of product and in the inactivation of the enzyme was determined to be 283 +/- 21. The present study's results, together with our previous findings, which proved that both 8-hydroxydaidzein and 8-hydroxygenistein are suicide substrates of mushroom tyrosinase, show that 7,8,4'-trihydroxyl functional groups on flavonoids' skeletons play important roles in producing suicide substrate properties toward mushroom tyrosinase.

Complete Isolation and Characterization of Polar Portion of Mentha dumetorum Water Extract

Directory of Open Access Journals (Sweden)

Hüseyin Akşit

2014-05-01

Full Text Available Four flavon glycosides, eriocitrin (1, luteolin-7-O-rutinoside (2, hesperidin (3, apigenin-7-O-rutinoside (4 and rosmarinic acid (5 were isolated from the aerial parts of Mentha dumetorum (Lamiaceae for the first time. The structural elucidations of isolated compounds were achieved using spectral methods (1D- and 2D-NMR, and LC-TOF-HRMS.

Thermodynamic modeling of naringenin protonation equilibria in ...

Indian Academy of Sciences (India)

metric studies in reducing the capabilities of flavonoids indicate that antioxidant ability ... the degree of ionization. For this reason, accurate knowledge of the ionization ..... Berry R S, Rice S A and Ross J 1980 In Physical. Chemistry (New York: ...

Optimizing culture medium for debittering constitutive enzyme ...

African Journals Online (AJOL)

STORAGESEVER

2010-08-02

Aug 2, 2010 ... naringinase on different matrices has been studied by many researchers (Busto et ... 10 g/L in the base medium compared to naringin control. Nitrogen ... Fermentation experiments were carried out in shaking flask for 5 days at 28°C with initial pH 6.0. † Values ..... fujikuroi mycelium in fluidized bioreactors.

Metabolic engineering of yeast for fermentative production of flavonoids

DEFF Research Database (Denmark)

Rodriguez Prado, Edith Angelica; Strucko, Tomas; Stahlhut, Steen Gustav

2017-01-01

Yeast Saccharomyces cerevisiae was engineered for de novo production of six different flavonoids (naringenin, liquiritigenin, kaempferol, resokaempferol, quercetin, and fisetin) directly from glucose, without supplementation of expensive intermediates. This required reconstruction of long...... demonstrates the potential of flavonoid-producing yeast cell factories....

Effects of Glucosinolates and Flavonoids on Colonization of the Roots of Brassica napus by Azorhizobium caulinodans ORS571

Science.gov (United States)

O'Callaghan, Kenneth J.; Stone, Philip J.; Hu, Xiaojia; Griffiths, D. Wynne; Davey, Michael R.; Cocking, Edward C.

2000-01-01

Plants of Brassica napus were assessed quantitatively for their susceptibility to lateral root crack colonization by Azorhizobium caulinodans ORS571(pXLGD4) (a rhizobial strain carrying the lacZ reporter gene) and for the concentration of glucosinolates in their roots by high-pressure liquid chromatography (HPLC). High- and low-glucosinolate-seed (HGS and LGS) varieties exhibited a relatively low and high percentage of colonized lateral roots, respectively. HPLC showed that roots of HGS plants contained a higher concentration of glucosinolates than roots of LGS plants. One LGS variety showing fewer colonized lateral roots than other LGS varieties contained a higher concentration of glucosinolates than other LGS plants. Inoculated HGS plants treated with the flavonoid naringenin showed significantly more colonization than untreated HGS plants. This increase was not mediated by a naringenin-induced lowering of the glucosinolate content of HGS plant roots, nor did naringenin induce bacterial resistance to glucosinolates or increase the growth of bacteria. The erucic acid content of seed did not appear to influence colonization by azorhizobia. Frequently, leaf assays are used to study glucosinolates and plant defense; this study provides data on glucosinolates and bacterial colonization in roots and describes a bacterial reporter gene assay tailored easily to the study of ecologically important phytochemicals that influence bacterial colonization. These data also form a basis for future assessments of the benefits to oilseed rape plants of interaction with plant growth-promoting bacteria, especially diazotrophic bacteria potentially able to extend the benefits of nitrogen fixation to nonlegumes. PMID:10788398

The SOS Chromotest applied for screening plant antigenotoxic agents against ultraviolet radiation.

Science.gov (United States)

Fuentes, J L; García Forero, A; Quintero Ruiz, N; Prada Medina, C A; Rey Castellanos, N; Franco Niño, D A; Contreras García, D A; Córdoba Campo, Y; Stashenko, E E

2017-09-13

In this work, we investigated the usefulness of the SOS Chromotest for screening plant antigenotoxic agents against ultraviolet radiation (UV). Fifty Colombian plant extracts obtained by supercritical fluid (CO 2 ) extraction, twelve plant extract constituents (apigenin, carvacrol, β-caryophyllene, 1,8-cineole, citral, p-cymene, geraniol, naringenin, pinocembrin, quercetin, squalene, and thymol) and five standard antioxidant and/or photoprotective agents (curcumin, epigallocatechin gallate, resveratrol, α-tocopherol, and Trolox®) were evaluated for their genotoxicity and antigenotoxicity against UV using the SOS Chromotest. None of the plant extracts, constituents or agents were genotoxic in the SOS Chromotest at tested concentrations. Based on the minimal extract concentration that significantly inhibited UV-genotoxicity (CIG), five plant extracts were antigenotoxic against UV as follows: Baccharis nítida (16 μg mL -1 ) = Solanum crotonifolium (16 μg mL -1 ) > Hyptis suaveolens (31 μg mL -1 ) = Persea caerulea (31 μg mL -1 ) > Lippia origanoides (62 μg mL -1 ). Based on CIG values, the flavonoid compounds showed the highest antigenotoxic potential as follows: apigenin (7 μM) > pinocembrin (15 μM) > quercetin (26 μM) > naringenin (38 μM) > epigallocatechin gallate (108 μM) > resveratrol (642 μM). UV-genotoxicity inhibition with epigallocatechin gallate, naringenin and resveratrol was related to its capability for inhibiting protein synthesis. A correlation analysis between compound antigenotoxicity estimates and antioxidant activity evaluated by the oxygen radical absorbance capacity (ORAC) assay showed that these activities were not related. The usefulness of the SOS Chromotest for bioprospecting of plant antigenotoxic agents against UV was discussed.

Effects of flavonoid mixtures on the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers: An in vitro and kinetic modeling approach to predict the combined effects on transporter inhibition

NARCIS (Netherlands)

Schutte, M.E.; Boersma, M.G.; Verhallen, D.A.M.; Groten, J.P.; Rietjens, I.M.C.M.

2008-01-01

This study describes and kinetically models the effect of flavonoid mixtures on PhIP transport through Caco-2 monolayers. Previously it was shown that quercetin, luteolin, naringenin and myricetin increase the apical to basolateral PhIP transport in Caco-2 monolayers. In this study, apigenin was

HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products

DEFF Research Database (Denmark)

Mølgaard, Per; Johnsen, Søren; Christensen, Peter

2003-01-01

phenolics as well as the lipophilic alkamides are released from the samples, followed by the analytical HPLC procedure for quantitative determination of these compounds. The method is the first one validated for the determination of these two groups of compounds in the same procedure. Naringenin has been...

Industrial processing versus home processing of tomato sauce: Effects on phenolics, flavonoids and in vitro bioaccessibility of antioxidants.

Science.gov (United States)

Tomas, Merve; Beekwilder, Jules; Hall, Robert D; Sagdic, Osman; Boyacioglu, Dilek; Capanoglu, Esra

2017-04-01

The effect of industrial and home processing, in vitro gastrointestinal digestion, individual phenolic content, and antioxidant capacity of tomato into tomato sauce were investigated. Industrial processing of tomato fruit into sauce had an overall positive effect on the total antioxidant capacity (∼1.2-fold higher) compared to tomato fruit whereas home processing of tomato fruit into sauce led to a decrease in these values. Untargeted LC-QTOF-MS analysis revealed 31 compounds in tomato that changed upon processing, of which 18 could be putatively identified. Naringenin chalcone is only detectable in the fruit, while naringenin is strongly increased in the sauces. Rutin content increased by 36% in the industrial processed sauce whereas decreased by 26% in the home processed sauce when compared to fruit. According to the results of an in vitro gastrointestinal digestion model, industrial processing may lead to enhanced bioaccessibility of antioxidants. Copyright © 2016 Elsevier Ltd. All rights reserved.

Blueberries and Tofu: Friend or Foe?

Science.gov (United States)

D'Ascoli, Jennifer; Lee, Susanne

2004-03-01

Two flavonoids, naringenin and genistein found in blueberries and soybeans, respectively, scavenge free radicals and exhibit anti- breast and prostate cancer properties. When consumed in foods, these flavonoids usually are subject to heat, yet all biological studies have been performed with unheated molecules. We have explored and will report on the three-dimensional, molecular structure changes we have thermally-induced in naringenin and genistein. We have measured and will discuss the flavonoids' thermodynamic properties as a function of temperature. Several endothermic transformations were observed along with a marked color change that remained when the flavonoids were dissolved in a solvent, indicating their molecular structures had been altered by the heat. Ultraviolet-Visible spectroscopy, and proton and carbon 1-D nuclear magnetic resonance will be presented that show the change was associated with a decrease in electron localization within the molecules. We will explain how such modified structures could scavenge free radicals more effectively and affect breast cancer cell proliferation.

Identification of Three Kinds of Citri Reticulatae Pericarpium Based on Deoxyribonucleic Acid Barcoding and High-performance Liquid Chromatography-diode Array Detection-electrospray Ionization/Mass Spectrometry/Mass Spectrometry Combined with Chemometric Analysis

Science.gov (United States)

Yu, Xiaoxue; Zhang, Yafeng; Wang, Dongmei; Jiang, Lin; Xu, Xinjun

2018-01-01

Background: Citri Reticulatae Pericarpium is the dried mature pericarp of Citrus reticulata Blanco which can be divided into “Chenpi” and “Guangchenpi.” “Guangchenpi” is the genuine Chinese medicinal material in Xinhui, Guangdong province; based on the greatest quality and least amount, it is most expensive among others. Hesperidin is used as the marker to identify Citri Reticulatae Pericarpium described in the Chinese Pharmacopoeia 2010. However, both “Chenpi” and “Guangchenpi” contain hesperidin so that it is impossible to differentiate them by measuring hesperidin. Objective: Our study aims to develop an efficient and accurate method to separate and identify “Guangchenpi” from other Citri Reticulatae Pericarpium. Materials and Methods: The genomic deoxyribonucleic acid (DNA) of all the materials was extracted and then the internal transcribed spacer 2 was amplified, sequenced, aligned, and analyzed. The secondary structures were created in terms of the database and website established by Jörg Schultz et al. High-performance liquid chromatography-diode array detection-electrospray Ionization/mass spectrometry (HPLC-DAD-ESI-MS)/MS coupled with chemometric analysis was applied to compare the differences in chemical profiles of the three kinds of Citri Reticulatae Pericarpium. Results: A total of 22 samples were classified into three groups. The results of DNA barcoding were in accordance with principal component analysis and hierarchical cluster analysis. Eight compounds were deduced from HPLC-DAD-ESI-MS/MS. Conclusions: This method is a reliable and effective tool to differentiate the three Citri Reticulatae Pericarpium. SUMMARY The internal transcribed spacer 2 regions and the secondary structure among three kinds of Citri Reticulatae Pericarpium varied considerablyAll the 22 samples were analyzed by high-performance liquid chromatography (HPLC) to obtain the chemical profilesPrincipal component analysis and hierarchical cluster analysis

Determination of blood concentrations of main active compounds in Zi-Cao-Cheng-Qi decoction and their total plasma protein binding rates based on hollow fiber liquid phase microextraction coupled with high performance liquid chromatography.

Science.gov (United States)

Li, Miaomiao; Chen, Xuan; Hu, Shuang; Wang, Runqin; Peng, Xiaoli; Bai, Xiaohong

2018-01-01

Oil-in-salt hollow fiber liquid phase microextraction coupled with high performance liquid chromatography ultraviolet detection (HPLC-UV) was developed for determination of the blood concentrations of the main active compounds, hesperidin, honokiol, shikonin, magnolol, emodin and β,β'-dimethylacrylshikonin, after oral administration of Zi-Cao-Cheng-Qi decoction (ZCCQD) and their total plasma protein binding rates. In the procedure, a hollow fiber segment was immersed in organic solvent to fill the solvent in the fiber lumen and wall pore, and then the fiber was immersed into sodium chloride solution to cover a thin salt membrane on the fiber wall pore filling organic solvent. Various factors affecting the procedure, such as extraction solvent, sample phase pH, stirring rate, extraction time, NaCl concentration and fiber immersion time in the NaCl solution, were optimized. Under the optimum conditions, good linearities (r 2 ≥0.9905), low limits of detection (0.7-2.5ng/mL) or quantitation (1.2-12ng/mL), satisfactory precision (2.6%-12.8%) and accuracy (81.0%-114.2%) of this method, were observed. The results showed that, after oral administration of a 25g/kg dose, (1) the blood concentrations (at 0.5h) of hesperidin, honokiol, shikonin, magnolol, emodin and β,β'-dimethylacrylshikonin were 0.45, 0.40, 0.48, 0.74, 0.11 and 1.11μg/mL, respectively; (2) the total plasma protein binding rates of the six active compounds were 42.0% (hesperidin), 71.8% (honokiol), 64.6% (shikonin), 77.7% (magnolol), 75.3% (emodin) and 75.7% (β,β'-dimethylacrylshikonin), respectively. The proposed procedure coupled with HPLC shows obvious advantages, such as low solvent consumption, simple operation, high sensitivity and strong purifying and can be used for the determination of both the blood concentrations and total plasma protein binding rates of active compounds in traditional Chinese medicine. Copyright © 2017 Elsevier B.V. All rights reserved.

Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols

NARCIS (Netherlands)

Muir, S.R.; Collins, G.J.; Robinson, S.; Hughes, S.G.; Bovy, A.G.; Vos, de C.H.R.; Tunen, van A.J.; Verhoeven, M.E.

2001-01-01

Tomatoes are an excellent source of the carotenoid lycopene, a compound that is thought to be protective against prostate cancer. They also contain small amounts of flavonoids in their peel (|[sim]|5–10 mg/kg fresh weight), mainly naringenin chalcone and the flavonol rutin, a quercetin glycoside.

Investigation of three flavonoids binding to bovine serum albumin using molecular fluorescence technique

International Nuclear Information System (INIS)

Bi Shuyun; Yan Lili; Pang Bo; Wang Yu

2012-01-01

The three flavonoids including naringenin, hesperetin and apigenin binding to bovine serum albumin (BSA) at pH 7.4 was studied by fluorescence quenching, synchronous fluorescence and UV-vis absorption spectroscopic techniques. The results obtained revealed that naringenin, hesperetin and apigenin strongly quenched the intrinsic fluorescence of BSA. The Stern-Volmer curves suggested that these quenching processes were all static quenching processes. At 291 K, the value and the order of the binding constant were K A n aringenin) =4.08x10 4 A(hesperetin) =5.40x10 4 ∼K A(apigenin) =5.32x10 4 L mol -1 . The main binding force between the flavonoid and BSA was hydrophobic and electrostatic force. According to the Foerster theory of non-radiation energy transfer, the binding distances (r 0 ) were obtained as 3.36, 3.47 and 3.30 nm for naringenin-BSA, hesperetin-BSA and apigenin-BSA, respectively. The effect of some common ions such as Fe 3+ , Cu 2+ , Mg 2+ , Mn 2+ , Zn 2+ and Ca 2+ on the binding was also studied in detail. The competition binding was also performed. The apparent binding constant (K' A ) obtained suggested that one flavonoid had an obvious effect on the binding of another flavonoid to protein when they coexisted in BSA solution. - Highlights: → Quenchings of BSA fluorescence by the flavonoids was all static quenchings. → Synchronous fluorescence was applied to study the structural change of BSA. → Binding constant, binding site and binding force were determined. → Competition binding experiments were performed. → One flavonoid had an obvious effect on the binding of another one to BSA.

Phytochemical and chemosystematic studies of Euxylophora paraensis (Rutaceae)

International Nuclear Information System (INIS)

Isidoro, Marsele Machado; Silva, Maria Fatima das Gracas Fernandes da; Fernandes, Joao Batista; Vieira, Paulo Cezar; Arruda, Alberto C.; Silva, Sebastiao da Cruz

2012-01-01

Phytochemical studies of the leaves and stem have led to the identification of the known coumarins isooxypeucedanin, oxypeucedanin hydrate, xanthotoxin, isopimpinellin, 8-methoxymarmesin and marmesin, flavonoids quercetin-3-O-α-L-rhamnopyranoside, myricetin-3-O-α-L-rhamnopyranoside and hesperidin, alkaloids skimmianine and N-methylflindersine and limonoid limonin. The compounds isolated and the chemical profile of Euxylophora obtained from the literature clearly indicate its phytochemical affinities with other Rutoideae species. (author)

Phytochemical and chemosystematic studies of Euxylophora paraensis (Rutaceae); Fitoquimica e quimiossistematica de Euxylophora paraensis (Rutaceae)

Energy Technology Data Exchange (ETDEWEB)

Isidoro, Marsele Machado; Silva, Maria Fatima das Gracas Fernandes da; Fernandes, Joao Batista; Vieira, Paulo Cezar [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Arruda, Alberto C.; Silva, Sebastiao da Cruz, E-mail: dmfs@ufscar.br [Universidade Federal do Para (UFPA), Belem, PA (Brazil). Fac. de Quimica

2012-07-01

Phytochemical studies of the leaves and stem have led to the identification of the known coumarins isooxypeucedanin, oxypeucedanin hydrate, xanthotoxin, isopimpinellin, 8-methoxymarmesin and marmesin, flavonoids quercetin-3-O-{alpha}-L-rhamnopyranoside, myricetin-3-O-{alpha}-L-rhamnopyranoside and hesperidin, alkaloids skimmianine and N-methylflindersine and limonoid limonin. The compounds isolated and the chemical profile of Euxylophora obtained from the literature clearly indicate its phytochemical affinities with other Rutoideae species. (author)

Dietary Regulation of PTEN Signaling and Mammary Tumor Initiating Cells: Implications for Breast Cancer Prevention

Science.gov (United States)

2012-07-01

turmeric [37], resveratrol from grape [38], capsaicin from chili pepper [39], flavonoids such as hesperetin and naringenin in citrus fruits and tomatoes... flavonoids and citrus juices. Nutr Cancer 1996;26:167–81. [41] Tomar RS, Shiao R. Early life and adult exposure to isoflavones and breast cancer risk. J

Evaluation of the diuretic potentials of naringenin in ...

African Journals Online (AJOL)

Tropical Journal of Pharmaceutical Research February 2018; 17 (2): 239- ... were placed in metabolic cages and urine samples were collected at two time-points (5 and 24 ... acute renal dysfunction from fluid shifts and ..... inflammation in mice.

Effect of Flavonoids on Glutathione Level, Lipid Peroxidation and Cytochrome P450 CYP1A1 Expression in Human Laryngeal Carcinoma Cell Lines

Directory of Open Access Journals (Sweden)

Lidija Vuković

2007-01-01

Full Text Available Flavonoids are phytochemicals exhibiting a wide range of biological activities, among which are antioxidant activity, the ability to modulate activity of several enzymes or cell receptors and possibility to interfere with essential biochemical pathways. Using human laryngeal carcinoma HEp2 cells and their drug-resistant CK2 subline, we examined the effect of five flavonoids, three structurally related flavons (quercetin, fisetin, and myricetin, one flavonol (luteolin and one glycosilated flavanone (naringin for: (i their ability to inhibit mitochondrial dehydrogenases as an indicator of cytotoxic effect, (ii their influence on glutathione level, (iii antioxidant/prooxidant effects and influence on cell membrane permeability, and (iv effect on expression of cytochrome CYP1A1. Cytotoxic action of the investigated flavonoids after 72 hours of treatment follows this order: luteolin>quercetin>fisetin>naringin>myricetin. Our results show that CK2 were more resistant to toxic concentrations of flavonoids as compared to parental cells. Quercetin increased the total GSH level in both cell lines. CK2 cells are less perceptible to lipid peroxidation and damage caused by free radicals. Quercetin showed prooxidant effect in both cell lines, luteolin only in HEp2 cells, whereas other tested flavonoids did not cause lipid peroxidation in the tested cell lines. These data suggest that the same compound, quercetin, can act as a prooxidant, but also, it may prevent damage in cells caused by free radicals, due to the induction of GSH, by forming less harmful complex. Quercetin treatment damaged cell membranes in both cell lines. Fisetin caused higher cell membrane permeability only in HEp2 cells. However, these two compounds did not enhance the damage caused by hydrogen peroxide. Quercetin, naringin, myricetin and fisetin increased the expression of CYP1A1 in both cell lines, while luteolin decreased basal level of CYP1A1 only in HEp2 cells. In conclusion, small

In vitro inhibition of canine distemper virus by flavonoids and phenolic acids: implications of structural differences for antiviral design.

Science.gov (United States)

Carvalho, O V; Botelho, C V; Ferreira, C G T; Ferreira, H C C; Santos, M R; Diaz, M A N; Oliveira, T T; Soares-Martins, J A P; Almeida, M R; Silva, A

2013-10-01

Infection caused by canine distemper virus (CDV) is a highly contagious disease with high incidence and lethality in the canine population. Antiviral activity of flavonoids quercetin, morin, rutin and hesperidin, and phenolic cinnamic, trans-cinnamic and ferulic acids were evaluated in vitro against the CDV using the time of addition assay to determine which step of the viral replicative cycle was affected. All flavonoids displayed great viral inhibition when they were added at the times 0 (adsorption) and 1h (penetration) of the viral replicative cycle. Both quercetin and hesperidin presented antiviral activity at the time 2h (intracellular). In the other hand, cinnamic acid showed antiviral activity at the times 0 and 2h while trans-cinnamic acid showed antiviral effect at the times -1h (pre-treatment) and 0 h. Ferulic acid inhibited CDV replicative cycle at the times 0 and 1h. Our study revealed promising candidates to be considered in the treatment of CDV. Structural differences among compounds and correlation to their antiviral activity were also explored. Our analysis suggest that these compounds could be useful in order to design new antiviral drugs against CDV as well as other viruses of great meaning in veterinary medicine. Copyright © 2013 Elsevier Ltd. All rights reserved.

Multi-omics approach to elucidate the gut microbiota activity: Metaproteomics and metagenomics connection.

Science.gov (United States)

Guirro, Maria; Costa, Andrea; Gual-Grau, Andreu; Mayneris-Perxachs, Jordi; Torrell, Helena; Herrero, Pol; Canela, Núria; Arola, Lluís

2018-02-10

Over the last few years, the application of high-throughput meta-omics methods has provided great progress in improving the knowledge of the gut ecosystem and linking its biodiversity to host health conditions, offering complementary support to classical microbiology. Gut microbiota plays a crucial role in relevant diseases such as obesity or cardiovascular disease (CVD), and its regulation is closely influenced by several factors, such as dietary composition. In fact, polyphenol-rich diets are the most palatable treatment to prevent hypertension associated with CVD, although the polyphenol-microbiota interactions have not been completely elucidated. For this reason, the aim of this study was to evaluate microbiota effect in obese rats supplemented by hesperidin, after being fed with cafeteria or standard diet, using a multi meta-omics approaches combining strategy of metagenomics and metaproteomics analysis. We reported that cafeteria diet induces obesity, resulting in changes in the microbiota composition, which are related to functional alterations at proteome level. In addition, hesperidin supplementation alters microbiota diversity and also proteins involved in important metabolic pathways. Overall, going deeper into strategies to integrate omics sciences is necessary to understand the complex relationships between the host, gut microbiota, and diet. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Hesperidin effects on behavior and locomotor activity of diabetic ...

African Journals Online (AJOL)

Tuoyo Aghomotsegin

2016-11-09

Nov 9, 2016 ... causing behavioral disorders, depression and cognitive dysfunction .... to control which was analysed using Student's t-test, at P<0.05. RESULTS .... music is used as a therapy that modulates a combined predator and noise ...

Hesperidin effects on behavior and locomotor activity of diabetic ...

African Journals Online (AJOL)

Tuoyo Aghomotsegin

2016-11-09

Nov 9, 2016 ... Author(s) agree that this article remains permanently open access under the terms of the Creative ... diabetes in animals and patients with type1 (Northam et ... measured were, locomotor activities, standing position, the time of.

Hesperidin effects on behavior and locomotor activity of diabetic ...

African Journals Online (AJOL)

African Journal of Biotechnology ... Today, there are sufficient validated scientific data that support the existence of relations between diabetes and certain ... disorders, such as behavioral disorders, anxiety, cognitive decline and depression.

Naturally occurring flavonoids against human norovirus surrogates.

Science.gov (United States)

Su, Xiaowei; D'Souza, Doris H

2013-06-01

Naturally occurring plant-derived flavonoids are reported to have antibacterial, antiviral, and pharmacological activities. The objectives of this study were to determine the antiviral effects of four flavonoids (myricetin, L-epicatechin, tangeretin, and naringenin) on the infectivity of food borne norovirus surrogates after 2 h at 37 °C. The lab-culturable surrogates, feline calicivirus (FCV-F9) at titers of ~7 log₁₀ PFU/ml (high titer) or ~5 log₁₀ PFU/ml (low titer) and murine norovirus (MNV-1) at ~5 log₁₀ PFU/ml, were mixed with equal volumes of myricetin, L-epicatechin, tangeretin, or naringenin at concentrations of 0.5 or 1 mM, and incubated for 2 h at 37 °C. Treatments of viruses were neutralized in cell culture medium containing 10 % heat-inactivated fetal bovine serum, serially diluted, and plaque assayed. Each treatment was replicated thrice and assayed in duplicate. FCV-F9 (low titer) was not found to be reduced by tangeretin or naringenin, but was reduced to undetectable levels by myricetin at both concentrations. Low titer FCV-F9 was also decreased by 1.40 log₁₀ PFU/ml with L-epicatechin at 0.5 mM. FCV-F9 at high titers was decreased by 3.17 and 0.72 log₁₀ PFU/ml with myricetin and L-epicatechin at 0.5 mM, and 1.73 log10 PFU/ml with myricetin at 0.25 mM, respectively. However, MNV-1 showed no significant inactivation by the four tested treatments. The antiviral effects of the tested flavonoids are dependent on the virus type, titer, and dose. Further research will focus on understanding the antiviral mechanism of myricetin and L-epicatechin.

[Separation and identification of specific components and quality standard of stem of Dendrobium officinale].

Science.gov (United States)

Ye, Zi; Lu, Ye; Xue, Ya-Fu; Xu, Hong; Wang, Zheng-Tao

2016-07-01

The violanthin, a specific component, was separated and identified from the stems of Dendrobium officinale by chromatographic technique and spectroscopic method for the first time. The microscopic characteristics of D. officinale powder were examined under a microscopy and described. Thin layer chromatography (TLC) method was used for qualitative analysis of the violanthin from D. officinale stems with a mixture of ethyl acetate, butanone, formic acid and water (4∶3∶1∶1) as the developing solvent on high performance silica gel precoated plate (SGF254) and using aluminium trichloride as a chromagenic agent. The results showed significant characteristics of violanthin from D. officinale stems on TLC, with certain specificity, and could be used to distinguish it from other easily confusing processed medicinal stems of D. devonianum, D. gratiosissimum and D. aphyllum. The content of naringenin, an active ingredient in D. officinale stems was determined by HPLC analysis on a Bischoff Chromatography HIPAK NC-04 ODS AB column (4.4 mm×250 mm, 5 mm) with acetonitrile-0.1% phosphoric acid solution as the mobile phase for gradient elution. The wavelength was set at 226 nm and column temperature was 25 ℃. The HPLC method showed good linearity within the range of 3.90-250.00 g•mL⁻¹ (r = 0.999 9) for naringenin. The average recovery of naringenin was 99.20% with 0.17% of RSD. The mass fraction of 20 batches of D. officinale stems was between 0.190 and 0.498 mg•g⁻¹. The established qualitative and quantitative method was simple and rapid with good repeatability and accuracy, providing experimental basis for improving the quality standard of D. officinale, with a very important significance to ensure its quality and clinical effect. Copyright© by the Chinese Pharmaceutical Association.

Antimicrobial activity of Helichrysum plicatum DC

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Bigović Dubravka J.

2017-01-01

Full Text Available Dry flower heads of Helichrysum plicatum were characterized by HPLC-DAD and a detailed antimicrobial assay of its ethanol extract was performed. Identification of phenolic compounds indicated the presence of apigenin, naringenin and kaempferol as free aglycones, glycosides of apigenin, naringenin, quercetin and kaempferol as well as chlorogenic acid and chalcone derivate. Antimicrobial activity of the extract was evaluated against various bacteria and fungi as well as yeast Candida albicans using microdilution method. Grampositive bacteria were more sensitive to the tested extract (MIC values were to 0.02 mg/mL than Gram-negative bacteria (the greatest MIC was 0.055 mg/mL. Regarding pathogenic fungi, our tests demonstrated that fungi were more sensitive to the tested extract than bacteria. The growth of the majority of the tested fungi was inhibited by concentration of 0.005 mg/mL. Moreover, the extract was significantly more active than commercial fungicide, fluconazole. The results of our tests indicate that the extract of H. plicatum has significant antimicrobial activity and may find application in the pharmaceutical and food industry and organic agriculture.

Flavonoid Analyses and Antimicrobial Activity of Various Parts of Phaleria macrocarpa (Scheff. Boerl Fruit

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Ehsan Oskoueian

2011-05-01

Full Text Available Phaleria macrocarpa (Scheff. Boerl (Thymelaceae is commonly known as ‘Crown of God’, ‘Mahkota Dewa’, and ‘Pau’. It originates from Papua Island, Indonesia and it grows in tropical areas. Empirically, it is potent in treating the hypertensive,diabetic, cancer and diuretic patients. It has a long history of ethnopharmacological usage, and the lack of information about its biological activities led us to investigate the possible biological activities by characterisation of flavonoids and antimicrobial activity of various part of P. macrocarpa against pathogenic bacteria and fungi. The results showed that kaempferol, myricetin, naringin, and rutin were the major flavonoids present in the pericarp while naringin and quercetin were found in the mesocarp and seed. Furthermore, the antibacterial activity of different parts of P. macrocarpa fruit showed a weak ability to moderate antibacterial activity against pathogenic tested bacteria (inhibition range: 0.93–2.17 cm at concentration of 0.3 mg/disc. The anti fungi activity was only found in seed extract against Aspergillus niger (1.87 cm at concentration of 0.3 mg/well. From the results obtained, P. macrocarpa fruit could be considered as a natural antimicrobial source due to the presence of flavonoid compounds.

Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities

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Cynthia Q. Sun

2017-11-01

Full Text Available Enzymatic conjugation with fatty acids including omega-3 polyunsaturated fatty acids (ω-3 PUFAs derived from fish oil to three citrus fruit-derived flavonoids: grapefruit extract, naringin, and neohesperidin dihydrochalcone were investigated. The conversions were achieved over 85% under the catalysis of lipase Novozyme 435 in acetone at 45°C at semi-preparative scale. The conjugates were purified via solvent partition and silica gel chromatography and achieved 90–98% in purity. The NMR analysis of the conjugates confirmed that the fatty acid carbon chain was linked onto the primary –OH group on the glucose moiety of the flavonoids. The purified flavonoid conjugates alongside their original flavonoids were analyzed for antioxidant activities via 2,2-diphenyl-1-picrylhydrazyl scavenging assay, and anti-peroxidation test via peroxide values measured during a 1-week fish oil storage trial. Vascular endothelial growth factor (VEGF assay was conducted with 1, 10, and 100 μM of naringin and grapefruits and their conjugates, respectively, and total VEGF levels were measured at 24 and 48 h, respectively, using ELISA and dot blot analysis. The results from these functionality experiments demonstrated that flavonoid FA conjugates have at least comparable (if not higher antioxidant activity, anti-peroxidation activity, and anti-angiogenic activity.

Antiallergic activity of unripe Citrus hassaku fruits extract and its flavanone glycosides on chemical substance-induced dermatitis in mice.

Science.gov (United States)

Itoh, Kimihisa; Masuda, Megumi; Naruto, Shunsuke; Murata, Kazuya; Matsuda, Hideaki

2009-10-01

Oral administration of a 50% ethanolic extract (CH-ext) obtained from unripe Citrus hassaku fruits collected in July exhibited a potent dose-dependent inhibition of IgE (immunoglobulin E)-mediated triphasic cutaneous reaction at 1 h [immediate phase response (IPR)], 24 h [late phase response (LPR)] and 8 days [very late phase response (vLPR)] after dinitrofluorobenzene challenge in mice. Naringin, a major flavanone glycoside component of CH-ext, showed a potent dose-dependent inhibition against IPR, LPR and vLPR. Neohesperidin, another major glycoside component of CH-ext, showed an inhibition against vLPR. The effect of CH-ext on type IV allergic reaction was examined by determining inhibitory activity against ear swelling in mice by using the picryl chloride-induced contact dermatitis (PC-CD) model. Oral administration (p.o.) of CH-ext and subcutaneous administration (s.c.) of prednisolone inhibited ear swelling during the induction phase of PC-CD. The inhibitory activities of combinations of CH-ext (p.o.) and prednisolone (s.c.) against PC-CD in mice were more potent than those of CH-ext alone and prednisolone alone, without enhancing the adverse effects. Other combinations of prednisolone (s.c.) and flavanone glycoside (p.o.) components of CH-ext, i.e. naringin and neohesperidin, exerted similar synergistic effects.

Absorption and pharmacokinetics of grapefruit flavanones in beagles

OpenAIRE

Mata Bilbao, María de Lourdes; Andrés Lacueva, Ma. Cristina; Roura Carvajal, Elena; Jáuregui Pallarés, Olga; Escribano Ferrer, Elvira; Torre, Celina; Lamuela Raventós, Rosa Ma.

2007-01-01

The present study evaluated the pharmacokinetics of three different grapefruit flavanone forms in dog plasma and demonstrated their absorption after an oral intake of a grapefruit extract; pharmacokinetic parameters of these forms were also determined. Ten healthy beagles were administered 70 mg citrus flavonoids as a grapefruit extract contained in capsules, while two additional dogs were used as controls and given an excipient. The grapefruit flavanone naringin, along with its metabolites n...

Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation.

Science.gov (United States)

Paysant, J; Sansilvestri-Morel, P; Bouskela, E; Verbeuren, T J

2008-02-01

This study evaluated microcirculatory effects of the flavonoid substances that constitute the micronized purified flavonoid fraction (MPFF) (Daflon 500 mg) in comparison to diosmin. In groups of 3 male hamsters, oral treatment with MPFF or diosmin (15 min before anesthesia) did not alter blood pressure. At 10 or 30 mg/kg, both MPFF and diosmin significantly decreased the leaky sites caused by ischemia/reperfusion (I/R) (30 min) in the hamster cheek pouch; the effect was significantly higher with MPFF (39+/-1% and 52+/-1%, respectively) than diosmin (18+/-1% and 37+/-3%, respectively). Eight groups of 3 hamsters each were treated with the components of MPFF. Diosmetin only decreased the number leaky sites at 30 mg/kg (decrease: 15+/-2%). The decrement at 10 and 30 mg/kg averaged at: 17+/-3% and 44+/-1%, respectively, for hesperidin; 19+/-1% and 46+/-2%, respectively, for linarin; and 30+/-1% and 44+/-1%, respectively, for isorhoifolin. Hesperidin, linarin, and isorhoifolin each displayed an anti-leakage effect comparable to or greater than diosmin. MPFF decreases permeability more than any of its single constituents, suggesting that the flavonoids present in its formulation have a synergistic action. These results illustrate that MPFF is more potent than single diosmin in this model of hyperpermeability and that each of the flavonoid substances present in MPFF contribute to its action.

Tıbbi Adaçayı (Salvia officinalis L.’nda Farklı Hasat Zamanlarının Uçucu Yağ ve Fenolik Bileşikler ile Antioksidan Aktivite Üzerine Etkisi

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Müge BAŞYİĞİT

2016-11-01

Full Text Available Bu araştırma, bir yıl süreyle 12 ayı temsil edecek şekilde farklı zamanlarda hasat edilen tıbbi adaçayı (Salvia officinalis L.’nın herba ve yaprak verimi, yaprakların taşıdığı uçucu yağ oranı ve kompozisyonu, ekstrede  Folin-Ciocalteu kolorimetrik metodu kullanılarak toplam fenolik madde miktarı, fenolik bileşikleri, serbest radikal süpürücü aktivitesi (DPPH ve demir iyonu indirgeme gücü (FRAP yöntemlerine göre antioksidan aktivitelerini belirlemek amacıyla yapılmıştır. Tıbbi adaçayında taze herba verimi 500.0-961.0 kg/da, kuru herba verimi 223.4-556.6 kg/da, kuru yaprak verimi 129.6-367.2 kg/da, uçucu yağ oranı %0.83-3.33, toplam fenolik madde miktarı 14.54-30.83 mg/g arasında değişim göstermiştir. Yaz ve güz aylarında hasat edilen bitkilerin herba ve yaprak verimleri, uçucu yağ oranları ve verimleri ile toplam fenolik madde miktarları kış ve bahar aylarında hasat edilen bitkilere göre daha yüksek bulunmuştur. Tıbbi adaçayının uçucu yağ kompozisyonunu oluşturan en önemli bileşenlerin 1,8-sineol (%11.93-31.87, α-tuyon (%15.72-26.26, β-tuyon (%4.51-27.67 ve kamfor (%3.65-23.02 olduğu, 1,8-sineol ve kamfor oranları ilkbahar aylarında daha düşük oranlarda, α- ve β-tuyon oranları ise ilkbahar aylarında daha yüksek oranlarda bulunduğu tespit edilmiştir. Tıbbi adaçayının en önemli fenolik bileşenlerinin ise rosmarinik asit (15.15-100.57 mg/g, naringin (9.59-41.81 mg/g, hesperidin (9.80-53.26 mg/g ve rutin (0.73-10.04 mg/g olduğu, en yüksek antioksidan aktivite Mayıs ve Haziran aylarında biçilen ve en düşük antioksidan aktivite ise Mart ve Nisan aylarında biçilen tıbbi adaçayı yapraklarında gözlenmiştir.

Nariginase of Aspergillus niger: Production optimization by response surface methodology and utilisation of ultrasound for extractionNaringinase de Aspergillus niger: Otimização da produção por metodologia de superfície de resposta e uso do ultrassom para extração

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Maria Antonia Pedrine Colabone Celligoi

2011-08-01

Full Text Available Brazil is the world's largest producer of orange and concentrated juice for export. Concentrated juice with high levels of naringin has excessive bitterness, which reduces the quality and value on the market. The debittering can be obtained by using naringinase, an enzymatic complex that degrades naringin. This study reports the production of naringinase by Aspergillus niger 426 utilizing both sugar cane molasses as carbon source and yeast extract as nitrogen source. Naringin was used as inducer. Five nitrogen sources were studied and yeast extract was found as the best one as 225.6 mU/mL of naringinase activity at 120 hours of fermentation was achivied. For optimization of naringinase production it was applied response-surface methodology, with 22 incomplete factorial design. An activity value of 354.26 mU/mL of naringinase was achivied when as independent variables yeast extract (14.0g/L and naringin (0.2g/L were used. When applied ultrasound waves at 20 kHz of intensity for 2 minutes in the fermented broth, the activity reached the highest value of 473.6 mU/mL. Thus, naringinase, this enzyme of great potential for biotechnological applications, has its production increased by using statistical design and ultrasound.O Brasil é o maior produtor mundial de laranja e de suco concentrado destinado à exportação. Sucos cítricos concentrados para exportação com níveis elevados de naringina são excessivamente amargos, o que reduz a qualidade e o valor comercial do produto. A redução do amargor pode ser obtida pela naringinase, um complexo enzimático que degrada a naringina. Neste trabalho Aspergillus niger 426 foi usado como produtor de naringinase utilizando matérias-prima da agroindústria, melaço como fonte de carbono e extrato de levedura como fonte de nitrogênio. Naringina foi usada como indutor. Dentre as cinco fontes de nitrogênio pesquisadas, extrato de levedura apresentou o melhor resultado de 225,6 mU/mL de naringinase em 120

Tracing phenolic compounds through manufacturing of edible films from orange and grapefruit peels

OpenAIRE

Hernández-Carrillo, J.G.; Valdez-Fragoso, A.; Welti-Chanes, J.; Mújica-Paz, H.

2015-01-01

Edible films naturally rich in phenolic compounds were prepared from orange and grapefruit peels. Free and total polyphenols were determined by Folin-Ciocalteau method and flavonoids were identified and quantified by HPLC in the manufacturing processes of films. Films from grapefruit and orange peel had 24.95 and 28.18 mg GAE/g (Gallic Acid Equivalents/g), respectively, retaining more than 50% of total phenolics from the raw material. Hesperidin (33.39 mg/g) was the main flavonoid in orange p...

SWITCH: a dynamic CRISPR tool for genome engineering and metabolic pathway control for cell factory construction in Saccharomyces cerevisiae.

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Vanegas, Katherina García; Lehka, Beata Joanna; Mortensen, Uffe Hasbro

2017-02-08

The yeast Saccharomyces cerevisiae is increasingly used as a cell factory. However, cell factory construction time is a major obstacle towards using yeast for bio-production. Hence, tools to speed up cell factory construction are desirable. In this study, we have developed a new Cas9/dCas9 based system, SWITCH, which allows Saccharomyces cerevisiae strains to iteratively alternate between a genetic engineering state and a pathway control state. Since Cas9 induced recombination events are crucial for SWITCH efficiency, we first developed a technique TAPE, which we have successfully used to address protospacer efficiency. As proof of concept of the use of SWITCH in cell factory construction, we have exploited the genetic engineering state of a SWITCH strain to insert the five genes necessary for naringenin production. Next, the naringenin cell factory was switched to the pathway control state where production was optimized by downregulating an essential gene TSC13, hence, reducing formation of a byproduct. We have successfully integrated two CRISPR tools, one for genetic engineering and one for pathway control, into one system and successfully used it for cell factory construction.

Optimization of flavanones extraction by modulating differential solvent densities and centrifuge temperatures.

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Chebrolu, Kranthi K; Jayaprakasha, G K; Jifon, J; Patil, Bhimanagouda S

2011-07-15

Understanding the factors influencing flavonone extraction is critical for the knowledge in sample preparation. The present study was focused on the extraction parameters such as solvent, heat, centrifugal speed, centrifuge temperature, sample to solvent ratio, extraction cycles, sonication time, microwave time and their interactions on sample preparation. Flavanones were analyzed in a high performance liquid chromatography (HPLC) and later identified by liquid chromatography and mass spectrometry (LC-MS). The five flavanones were eluted by a binary mobile phase with 0.03% phosphoric acid and acetonitrile in 20 min and detected at 280 nm, and later identified by mass spectral analysis. Dimethylsulfoxide (DMSO) and dimethyl formamide (DMF) had optimum extraction levels of narirutin, naringin, neohesperidin, didymin and poncirin compared to methanol (MeOH), ethanol (EtOH) and acetonitrile (ACN). Centrifuge temperature had a significant effect on flavanone distribution in the extracts. The DMSO and DMF extracts had homogeneous distribution of flavanones compared to MeOH, EtOH and ACN after centrifugation. Furthermore, ACN showed clear phase separation due to differential densities in the extracts after centrifugation. The number of extraction cycles significantly increased the flavanone levels during extraction. Modulating the sample to solvent ratio increased naringin quantity in the extracts. Current research provides critical information on the role of centrifuge temperature, extraction solvent and their interactions on flavanone distribution in extracts. Published by Elsevier B.V.

Bio-based synthesis of silver nanoparticles from orange waste: effects of distinct biomolecule coatings on size, morphology, and antimicrobial activity

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Barros CHN

2018-03-01

Full Text Available Caio Henrique Nasi de Barros, Guilherme Crispim Faria Cruz, Willian Mayrink, Ljubica Tasic Laboratory of Chemical Biology, Department of Organic Chemistry, Instituto de Química da Universidade Estadual de Campinas–Unicamp, Campinas, SP, Brazil Purpose: Despite the numerous reports on biological syntheses of silver nanoparticles (AgNPs, little is known about the composition of their capping agents, protein corona of plant extract-mediated synthesis, and their influence on the properties of AgNPs. Here, orange (Citrus sinensis waste was utilized as a source of an extract for AgNP synthesis (the protein corona composition of which was elucidated, and also as a starting material for hesperidin and nanocellulose extraction, which were used for bio-based AgNP synthesis. A comparison of the results using the two methods of synthesis is presented. Methods: AgNPs were synthesized using orange (C. sinensis peel extract (­Or-AgNPs in a biological route, and using hesperidin (Hsd-AgNPs and nanocellulose (extracted from oranges in a green chemical route. Characterization of nanoparticles was carried out using zeta potential and hydrodynamic size measurements, transmission electron microscopy, and X-ray diffraction. Elucidation of proteins from protein corona was performed via ultra performance liquid chromatography-tandem mass spectrometer experiments. Antimicrobial activity was assessed via minimum inhibitory concentration assays against Xanthomonas axonopodis pv. citri (Xac, the bacterium that causes citric canker in oranges. Results: Or-AgNPs were not completely uniform in morphology, having a size of 48.1±20.5 nm and a zeta potential of −19.0±0.4 mV. Stabilization was performed mainly by three proteins, which were identified by tandem mass spectrometry (MS/MS experiments. Hsd-AgNPs were smaller (25.4±12.5 nm and had uniform morphology. Nanocellulose provided a strong steric and electrostatic (−28.2±1.0 mV stabilization to the nanoparticles

Food Ingredient Extracts of Cyclopia subternata (Honeybush: Variation in Phenolic Composition and Antioxidant Capacity

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Maria A. Stander

2012-12-01

Full Text Available Cyclopia subternata plants are traditionally used for the production of the South African herbal tea, honeybush, and recently as aqueous extracts for the food industry. A C. subternata aqueous extract and mangiferin (a major constituent are known to have anti-diabetic properties. Variation in phenolic composition and antioxidant capacity is expected due to cultivation largely from seedlings, having implications for extract standardization and quality control. Aqueous extracts from 64 seedlings of the same age, cultivated under the same environmental conditions, were analyzed for individual compound content, total polyphenol (TP content and total antioxidant capacity (TAC in a number of assays. An HPLC method was developed and validated to allow quantification of xanthones (mangiferin, isomangiferin, flavanones (hesperidin, eriocitrin, a flavone (scolymoside, a benzophenone (iriflophenone-3-C-β-glucoside and dihydrochalcones (phloretin-3',5'-di-C-β-glucoside, 3-hydroxyphloretin-3',5'-di-C-hexoside. Additional compounds were tentatively identified using mass spectrometric detection, with the presence of the 3-hydroxyphloretin-glycoside, an iriflophenone-di-O,C-hexoside, an eriodictyol-di-C-hexoside and vicenin-2 being demonstrated for the first time. Variability of the individual phenolic compound contents was generally higher than that of the TP content and TAC values. Among the phenolic compounds, scolymoside, hesperidin and iriflophenone-3-C-β-glucoside contents were the most variable. A combination of the measured parameters could be useful in product standardization by providing a basis for specifying minimum levels.

Food ingredient extracts of Cyclopia subternata (Honeybush): variation in phenolic composition and antioxidant capacity.

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de Beer, Dalene; Schulze, Alexandra E; Joubert, Elizabeth; de Villiers, André; Malherbe, Christiaan J; Stander, Maria A

2012-12-07

Cyclopia subternata plants are traditionally used for the production of the South African herbal tea, honeybush, and recently as aqueous extracts for the food industry. A C. subternata aqueous extract and mangiferin (a major constituent) are known to have anti-diabetic properties. Variation in phenolic composition and antioxidant capacity is expected due to cultivation largely from seedlings, having implications for extract standardization and quality control. Aqueous extracts from 64 seedlings of the same age, cultivated under the same environmental conditions, were analyzed for individual compound content, total polyphenol (TP) content and total antioxidant capacity (TAC) in a number of assays. An HPLC method was developed and validated to allow quantification of xanthones (mangiferin, isomangiferin), flavanones (hesperidin, eriocitrin), a flavone (scolymoside), a benzophenone (iriflophenone-3-C-β-glucoside) and dihydrochalcones (phloretin-3',5'-di-C-β-glucoside, 3-hydroxyphloretin-3',5'-di-C-hexoside). Additional compounds were tentatively identified using mass spectrometric detection, with the presence of the 3-hydroxyphloretin-glycoside, an iriflophenone-di-O,C-hexoside, an eriodictyol-di-C-hexoside and vicenin-2 being demonstrated for the first time. Variability of the individual phenolic compound contents was generally higher than that of the TP content and TAC values. Among the phenolic compounds, scolymoside, hesperidin and iriflophenone-3-C-β-glucoside contents were the most variable. A combination of the measured parameters could be useful in product standardization by providing a basis for specifying minimum levels.

Antiradical and cytotoxic activity of different Helichrysum plicatum flower extracts.

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Bigović, Dubravka; Savikin, Katarina; Janković, Teodora; Menković, Nebojsa; Zdunić, Gordana; Stanojković, Tatjana; Djurić, Zorica

2011-06-01

Flowers of Helichrysum plicatum were extracted under different experimental conditions, and their antioxidant activity was determined by DPPH radical scavenging assay. Extracts obtained with higher concentration of ethyl acetate (90% or 100%) were found to contain the greatest amount of total phenolics (> 250 mg gallic acid equivalents/g of dried extract), and high correlation between total phenolic content and antiradical activity was observed (r = -0.79). Based on the total phenolic content and antiradical activity, some extracts were selected for investigation of cytotoxic activity toward PC3, HeLa and K562 human cancer cell lines in vitro. All tested extracts exhibited moderate activity against HeLa cells (41.9-42.1 microg/mL), whereas the extract obtained with 100% ethyl acetate was the most active against K562 and PC3 cell lines (25.9 and 39.2 microg/mL, respectively). Statistical analysis revealed significant correlation between total phenolic content and cytotoxic activity against PC3 and K562 cells. HPLC identification of phenolic compounds from the extracts indicated the presence of apigenin, naringenin and kaempferol as free aglycones, and glycosides of apigenin, naringenin, quercetin and kaempferol. Among aglycones, kaempferol displayed moderate cytostatic activity against all cell lines (24.8-64.7 microM).

Helichrysum arenarium subsp. arenarium: phenolic composition and antibacterial activity against lower respiratory tract pathogens.

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Gradinaru, Adina C; Silion, Mihaela; Trifan, Adriana; Miron, Anca; Aprotosoaie, Ana C

2014-01-01

The aim of this study was to investigate the phenolic content and antibacterial activity of the methanol extract from Helichrysum arenarium (L.) Moench subsp. arenarium inflorescences against lower respiratory tract pathogens (standard strains and clinical isolates). The extract was characterised by a total phenolic content of 160.17 mg/g. Several caffeic acid conjugates (chlorogenic acid and dicaffeoylquinic acids) and flavonoids (apigenin, naringenin, apigenin-7-O-glucoside and naringenin-O-hexosides) were identified as major constituents by HPLC-DAD-ESI-MS. Staphylococcus aureus ATCC 25923 was more susceptible to Helichrysum extract than Streptococcus pneumoniae ATCC 49619 (minimum inhibitory concentration [MIC] = 0.62  and 1.25 mg/mL, respectively). The extract exhibited similar antibacterial effects against methicillin-resistant S. aureus and penicillin-resistant S. pneumoniae clinical isolates (MIC = 2.5 mg/mL) displaying a higher activity against ampicillin-resistant Moraxella catarrhalis isolate (MIC = 0.15 mg/mL). The combination with ciprofloxacin exhibited additivity against both standard strains (fractional inhibitory concentration [FIC] index = 0.75 and 0.73) and S. aureus isolates (FIC index = 0.62) and synergy against S. pneumoniae isolates (FIC index = 0.5).

Crystal structure and enzymatic properties of chalcone isomerase from the Antarctic vascular plant Deschampsia antarctica Desv.

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Park, Sun-Ha; Lee, Chang Woo; Cho, Sung Mi; Lee, Hyoungseok; Park, Hyun; Lee, Jungeun; Lee, Jun Hyuck

2018-01-01

Chalcone isomerase (CHI) is an important enzyme for flavonoid biosynthesis that catalyzes the intramolecular cyclization of chalcones into (S)-flavanones. CHIs have been classified into two types based on their substrate specificity. Type I CHIs use naringenin chalcone as a substrate and are found in most of plants besides legumes, whereas type II CHIs in leguminous plants can also utilize isoliquiritigenin. In this study, we found that the CHI from the Antarctic plant Deschampsia antarctica (DaCHI1) is of type I based on sequence homology but can use type II CHI substrates. To clarify the enzymatic mechanism of DaCHI1 at the molecular level, the crystal structures of unliganded DaCHI1 and isoliquiritigenin-bound DaCHI1 were determined at 2.7 and 2.1 Å resolutions, respectively. The structures revealed that isoliquiritigenin binds to the active site of DaCHI1 and induces conformational changes. Additionally, the activity assay showed that while DaCHI1 exhibits substrate preference for naringenin chalcone, it can also utilize isoliquiritigenin although the catalytic activity was relatively low. Based on these results, we propose that DaCHI1 uses various substrates to produce antioxidant flavonoids as an adaptation to oxidative stresses associated with harsh environmental conditions.

Crystal structure and enzymatic properties of chalcone isomerase from the Antarctic vascular plant Deschampsia antarctica Desv.

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Sun-Ha Park

Full Text Available Chalcone isomerase (CHI is an important enzyme for flavonoid biosynthesis that catalyzes the intramolecular cyclization of chalcones into (S-flavanones. CHIs have been classified into two types based on their substrate specificity. Type I CHIs use naringenin chalcone as a substrate and are found in most of plants besides legumes, whereas type II CHIs in leguminous plants can also utilize isoliquiritigenin. In this study, we found that the CHI from the Antarctic plant Deschampsia antarctica (DaCHI1 is of type I based on sequence homology but can use type II CHI substrates. To clarify the enzymatic mechanism of DaCHI1 at the molecular level, the crystal structures of unliganded DaCHI1 and isoliquiritigenin-bound DaCHI1 were determined at 2.7 and 2.1 Å resolutions, respectively. The structures revealed that isoliquiritigenin binds to the active site of DaCHI1 and induces conformational changes. Additionally, the activity assay showed that while DaCHI1 exhibits substrate preference for naringenin chalcone, it can also utilize isoliquiritigenin although the catalytic activity was relatively low. Based on these results, we propose that DaCHI1 uses various substrates to produce antioxidant flavonoids as an adaptation to oxidative stresses associated with harsh environmental conditions.

Hepatic Metabolism of Sakuranetin and Its Modulating Effects on Cytochrome P450s and UDP-Glucuronosyltransferases

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Hyesoo Jeong

2018-06-01

Full Text Available Sakuranetin (SKN, found in cherry trees and rice, is a flavanone with various pharmacological activities. It is biosynthesized from naringenin in rice or cherry trees, and the metabolism of SKN has been studied in non-human species. The present study aimed to investigate the metabolic pathways of SKN in human liver microsomes and identify the phase I and phase II metabolites, as well as evaluate the potential for drug–herb interactions through the modulation of drug metabolizing enzymes (DMEs. HPLC-DAD and HPLC-electrospray mass spectrometry were used to study the metabolic stability and identify the metabolites from human liver microsomes incubated with SKN. The potential of SKN to inhibit the DMEs was evaluated by monitoring the formation of a DME-specific product. The cytochrome P450 2B6 and 3A4-inductive effects were studied using promoter reporter assays in human hepatocarcinoma cells. The major pathways for SKN metabolism include B-ring hydroxylation, 5-O-demethylation, and conjugation with glutathione or glucuronic acid. The phase I metabolites were identified as naringenin and eriodictyol. SKN was found to be a UDP-glucuronosyltransferases (UGT 1A9 inhibitor, whereas it induced transactivation of the human pregnane X receptor-mediated cytochrome P450 (CYP 3A4 gene.

Influence of kinnow juice on the bioavailability of carbamazepine in healthy male volunteers.

Science.gov (United States)

Garg, S K; Bhargava, V K; James, H; KuJan-Mar, N; Prabhakar, S; Naresh, Ku

1998-01-01

Kinnow juice produces a marked and variable increase in carbamazepine bioavailability. The pharmacokinetics of carbamazepine was studied after drug administration with 300 ml water or kinnow juice in a randomized cross over trial on nine healthy male volunteers. With kinnow juice peak serum concentration (Cmax) and area under the serum concentration time curve (AUC) was significantly (P kinnow juice enhances carbamazepine bioavailability could be due to inhibition of cytochrome P-450 enzyme, since kinnow juice contains naringin which is considered to be inhibitor of liver microsomal dihydropyridine oxidation.

Flavonoids of Helichrysum compactum and their antioxidant and antibacterial activity.

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Süzgeç, Sevda; Meriçli, Ali H; Houghton, Peter J; Cubukçu, Bayhan

2005-03-01

From the capitula of Helichrysum compactum, the flavonoids apigenin, kaempferol, luteolin, naringenin, 3,5-dihydroxy-6,7,8-trimethoxyflavone, kaempferol-3-O-glucoside, luteolin-7-O-glucoside and luteolin-4',7-di-O-glucoside and from the leafy stems apigenin, kaempferol, luteolin, quercetin, apigenin-7-O-glucoside, luteolin-7-O-glucoside, and quercetin-3-O-glucoside were isolated. Extracts of the capitula of H. compactum show antioxidant activity by inhibition of lipid peroxidation and also show antibacterial activity.

Polyphenol levels in human urine after intake of six different polyphenol-rich beverages.

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Ito, Hideyuki; Gonthier, Marie-Paule; Manach, Claudine; Morand, Christine; Mennen, Louise; Rémésy, Christian; Scalbert, Augustin

2005-10-01

Dietary polyphenols are suggested to participate in the prevention of CVD and cancer. It is essential for epidemiological studies to be able to compare intake of the main dietary polyphenols in populations. The present paper describes a fast method suitable for the analysis of polyphenols in urine, selected as potential biomarkers of intake. This method is applied to the estimation of polyphenol recovery after ingestion of six different polyphenol-rich beverages. Fifteen polyphenols including mammalian lignans (enterodiol and enterolactone), several phenolic acids (chlorogenic, caffeic, m-coumaric, gallic, and 4-O-methylgallic acids), phloretin and various flavonoids (catechin, epicatechin, quercetin, isorhamnetin, kaempferol, hesperetin, and naringenin) were simultaneously quantified in human urine by HPLC coupled with electrospray ionisation mass-MS (HPLC-electrospray-tandem mass spectrometry) with a run time of 6 min per sample. The method has been validated with regard to linearity, precision, and accuracy in intra- and inter-day assays. It was applied to urine samples collected from nine volunteers in the 24 h following consumption of either green tea, a grape-skin extract, cocoa beverage, coffee, grapefruit juice or orange juice. Levels of urinary excretion suggest that chlorogenic acid, gallic acid, epicatechin, naringenin or hesperetin could be used as specific biomarkers to evaluate the consumption of coffee, wine, tea or cocoa, and citrus juices respectively.

Analysis of flavonoids and the flavonoid structural genes in brown fiber of upland cotton.

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Hongjie Feng

Full Text Available BACKGROUND: As a result of changing consumer preferences, cotton (Gossypium Hirsutum L. from varieties with naturally colored fibers is becoming increasingly sought after in the textile industry. The molecular mechanisms leading to colored fiber development are still largely unknown, although it is expected that the color is derived from flavanoids. EXPERIMENTAL DESIGN: Firstly, four key genes of the flavonoid biosynthetic pathway in cotton (GhC4H, GhCHS, GhF3'H, and GhF3'5'H were cloned and studied their expression profiles during the development of brown- and white cotton fibers by QRT-PCR. And then, the concentrations of four components of the flavonoid biosynthetic pathway, naringenin, quercetin, kaempferol and myricetin in brown- and white fibers were analyzed at different developmental stages by HPLC. RESULT: The predicted proteins of the four flavonoid structural genes corresponding to these genes exhibit strong sequence similarity to their counterparts in various plant species. Transcript levels for all four genes were considerably higher in developing brown fibers than in white fibers from a near isogenic line (NIL. The contents of four flavonoids (naringenin, quercetin, kaempferol and myricetin were significantly higher in brown than in white fibers and corresponding to the biosynthetic gene expression levels. CONCLUSIONS: Flavonoid structural gene expression and flavonoid metabolism are important in the development of pigmentation in brown cotton fibers.

Flavonoids and Auxin Transport Inhibitors Rescue Symbiotic Nodulation in the Medicago truncatula Cytokinin Perception Mutant cre1

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Ng, Jason Liang Pin; Hassan, Samira; Truong, Thy T.; Hocart, Charles H.; Laffont, Carole; Frugier, Florian; Mathesius, Ulrike

2015-01-01

Initiation of symbiotic nodules in legumes requires cytokinin signaling, but its mechanism of action is largely unknown. Here, we tested whether the failure to initiate nodules in the Medicago truncatula cytokinin perception mutant cre1 (cytokinin response1) is due to its altered ability to regulate auxin transport, auxin accumulation, and induction of flavonoids. We found that in the cre1 mutant, symbiotic rhizobia cannot locally alter acro- and basipetal auxin transport during nodule initiation and that these mutants show reduced auxin (indole-3-acetic acid) accumulation and auxin responses compared with the wild type. Quantification of flavonoids, which can act as endogenous auxin transport inhibitors, showed a deficiency in the induction of free naringenin, isoliquiritigenin, quercetin, and hesperetin in cre1 roots compared with wild-type roots 24 h after inoculation with rhizobia. Coinoculation of roots with rhizobia and the flavonoids naringenin, isoliquiritigenin, and kaempferol, or with the synthetic auxin transport inhibitor 2,3,5,-triiodobenzoic acid, rescued nodulation efficiency in cre1 mutants and allowed auxin transport control in response to rhizobia. Our results suggest that CRE1-dependent cytokinin signaling leads to nodule initiation through the regulation of flavonoid accumulation required for local alteration of polar auxin transport and subsequent auxin accumulation in cortical cells during the early stages of nodulation. PMID:26253705

Antiviral activity of four types of bioflavonoid against dengue virus type-2

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Zandi Keivan

2011-12-01

Full Text Available Abstract Background Dengue is a major mosquito-borne disease currently with no effective antiviral or vaccine available. Effort to find antivirals for it has focused on bioflavonoids, a plant-derived polyphenolic compounds with many potential health benefits. In the present study, antiviral activity of four types of bioflavonoid against dengue virus type -2 (DENV-2 in Vero cell was evaluated. Anti-dengue activity of these compounds was determined at different stages of DENV-2 infection and replication cycle. DENV replication was measured by Foci Forming Unit Reduction Assay (FFURA and quantitative RT-PCR. Selectivity Index value (SI was determined as the ratio of cytotoxic concentration 50 (CC50 to inhibitory concentration 50 (IC50 for each compound. Results The half maximal inhibitory concentration (IC50 of quercetin against dengue virus was 35.7 μg mL-1 when it was used after virus adsorption to the cells. The IC50 decreased to 28.9 μg mL-1 when the cells were treated continuously for 5 h before virus infection and up to 4 days post-infection. The SI values for quercetin were 7.07 and 8.74 μg mL-1, respectively, the highest compared to all bioflavonoids studied. Naringin only exhibited anti-adsorption effects against DENV-2 with IC50 = 168.2 μg mL-1 and its related SI was 1.3. Daidzein showed a weak anti-dengue activity with IC50 = 142.6 μg mL-1 when the DENV-2 infected cells were treated after virus adsorption. The SI value for this compound was 1.03. Hesperetin did not exhibit any antiviral activity against DENV-2. The findings obtained from Foci Forming Unit Reduction Assay (FFURA were corroborated by findings of the qRT-PCR assays. Quercetin and daidzein (50 μg mL-1 reduced DENV-2 RNA levels by 67% and 25%, respectively. There was no significant inhibition of DENV-2 RNA levels with naringin and hesperetin. Conclusion Results from the study suggest that only quercetin demonstrated significant anti-DENV-2 inhibitory activities. Other

LC determination and pharmacokinetic study of the main phenolic components of Portulaca oleracea L. extract in rat plasma after oral administration.

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Cheng, Zhongzhe; Wang, Dong; Zhang, Wenjie; Du, Yang; Wang, Yunjiao; Zhai, Yanjun; Ying, Xixiang; Kang, Tingguo

2012-01-01

This study investigated the pharmacokinetics of hesperidin (HP), ferulic acid (FA) and p-coumaric acid (CA) in rat plasma after oral administration of Portulaca oleracea L. extract (POE). The plasma concentrations were determined by HPLC with vitexin-2″-O-rhamnoside (VR) as internal standard. The calibration curves were linear over the range 0.1-5 µg mL(-1), 0.1-5 µg mL(-1)and 0.015-3 µg mL(-1) for HP, FA and CA, respectively. The validated method was suitable to the pharmacokinetic study of HP, FA and CA in rats after oral administration at a single dose of POE.

Evaluation of flavonoids and enterolactone in overnight urine as intake biomarkers of fruits, vegetables and beverages in the Inter99 cohort study using the method of triads

DEFF Research Database (Denmark)

Krogholm, Kirstine Suszkiewicz; Bysted, Anette; Brantsaeter, A. L.

2012-01-01

in 24 h urine as an alternative and more feasible biomarker of fruit, vegetable and beverage intake. A total of 191 individuals in the Inter99 cohort in Denmark completed the validation study. Concentrations of nine urinary flavonoid aglycones (quercetin, isorhamnetin, tamarixetin, kaempferol......, hesperetin, naringenin, eriodictyol, phloretin and apigenin) and enterolactone were determined in overnight and 24 h urine samples, and their validity as biomarkers of fruit, vegetable and beverage intake was evaluated in relation to two independent reference methods (Inter99 FFQ data and plasma carotenoids...

Study of the chemical composition of the resinous exudate isolated from Heliotropium sclerocarpum and evaluation of the antioxidant properties of the phenolic compounds and the resin.

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Modak, Brenda; Salina, Melissa; Rodilla, Jesús; Torres, René

2009-11-12

Heliotropium sclerocarpum Phil. (Heliotropiaceae) is a resinous bush that grows in the Atacama of northern Chile. The chemical composition of its resinous exudate was analyzed for the first time. One aromatic geranyl derivative: filifolinol (1), one flavanone: naringenin (2) and a new type of 3-oxo-2-arylbenzofuran derivative 3 were isolated and their structures were determined. The antioxidant activity of the phenolic compounds and resin was evaluated using the bleaching of DPPH radical method and expressed as fast reacting equivalents (FRE) and total reacting equivalents (TRE).

Fingerprinting and validation of a LC-DAD method for the analysis of biflavanones in Garcinia kola-based antimalarial improved traditional medicines.

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Tshibangu, P Tshisekedi; Kapepula, P Mutwale; Kapinga, M J Kabongo; Lupona, H Kabika; Ngombe, N Kabamba; Kalenda, Dibungi T; Jansen, O; Wauters, J N; Tits, M; Angenot, L; Rozet, E; Hubert, Ph; Marini, R D; Frédérich, M

2016-09-05

African populations use traditional medicines in their initial attempt to treat a range of diseases. Nevertheless, accurate knowledge of the composition of these drugs remains a challenge in terms of ensuring the health of population and in order to advance towards improved traditional medicines (ITMs). In this paper chromatographic methods were developed for qualitative and quantitative analyses of a per os antimalarial ITM containing Garcinia kola. The identified analytical markers were used to establish TLC and HPLC fingerprints. G. kola seeds were analysed by HPLC to confirm the identity of the extract used by the Congolese manufacturer in the ITM. The main compounds (GB1, GB2, GB-1a and Kolaflavanone) were isolated by preparative TLC and identified by UPLC-MS and NMR. For the quantification of the major compound GB1, a simple and rapid experimental design was applied to develop an LC method, and then its validation was demonstrated using the total error strategy with the accuracy profile as a decision tool. The accurate results were observed within 0.14-0.45mg/mL range of GB1 expressed as naringenin. The extracts used in several batches of the analysed oral solutions contained GB1 (expressed as naringenin) within 2.04-2.43%. Both the fingerprints and the validated LC-DAD were found suitable for the quality control of G. kola-based raw material and finished products, respectively. Copyright © 2016 Elsevier B.V. All rights reserved.

[Simultaneous determination of 16 flavonoids in the ginkgo dietary supplement tea by high performance liquid chromatography-tandem mass spectrometry].

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Jiang, Yalan; Huang, Fang; Wu, Fuhai; Wu, Huiqin; Huang, Xiaolan; Deng, Xin

2015-10-01

A method for the determination of 16 functional components of ginkgo dietary supplement tea such as catechin, vitexin, puerarin, isoflavoues aglycone, silymarin, quercetin, luteolin, apigenin, naringenin, hesperitin dihydrochalcone, kaempferol, hesperitin, isorhamnetin, baicalein, nobiletin and tangeretin by high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) was proposed. The conditions of chromatography and mass spectrometry were optimized. The 16 flavonoids were separated on a C18 chromatographic column with acetonitrile and water (additional 0.1% formic acid) as mobile phases under gradient elution at a flow rate of 0.25 mL/min. The determination was conducted by tandem mass spectrometry in positive ESI mode under multiple reaction monitoring (MRM) mode. Good linearities for all the compounds, with correlation coefficients over 0.996, were acquired. The recoveries were in the range of 70.9% to 100.0% (n = 6), while the relative standard deviations (RSDs) were less than 10%. The results showed that the nine flavonoids, which were kaempferol, quercetin, hesperitin, vitexin, luteolin, catechin, apigenin, naringenin and isorhamnetin, were higher in contents among the 16 flavonoids in real samples, and they constituted up to 99.6% of the total flavonoids. The contents of these nine flavonoids can be considered as the quality control index of the ginkgo dietary supplement tea. The method proved to be rapid, selective, sensitive and stable, and it can be applied to control the quality of the ginkgo dietary supplement tea.

Flavonoids act as negative regulators of auxin transport in vivo in arabidopsis

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Brown, D. E.; Rashotte, A. M.; Murphy, A. S.; Normanly, J.; Tague, B. W.; Peer, W. A.; Taiz, L.; Muday, G. K.

2001-01-01

Polar transport of the plant hormone auxin controls many aspects of plant growth and development. A number of synthetic compounds have been shown to block the process of auxin transport by inhibition of the auxin efflux carrier complex. These synthetic auxin transport inhibitors may act by mimicking endogenous molecules. Flavonoids, a class of secondary plant metabolic compounds, have been suggested to be auxin transport inhibitors based on their in vitro activity. The hypothesis that flavonoids regulate auxin transport in vivo was tested in Arabidopsis by comparing wild-type (WT) and transparent testa (tt4) plants with a mutation in the gene encoding the first enzyme in flavonoid biosynthesis, chalcone synthase. In a comparison between tt4 and WT plants, phenotypic differences were observed, including three times as many secondary inflorescence stems, reduced plant height, decreased stem diameter, and increased secondary root development. Growth of WT Arabidopsis plants on naringenin, a biosynthetic precursor to those flavonoids with auxin transport inhibitor activity in vitro, leads to a reduction in root growth and gravitropism, similar to the effects of synthetic auxin transport inhibitors. Analyses of auxin transport in the inflorescence and hypocotyl of independent tt4 alleles indicate that auxin transport is elevated in plants with a tt4 mutation. In hypocotyls of tt4, this elevated transport is reversed when flavonoids are synthesized by growth of plants on the flavonoid precursor, naringenin. These results are consistent with a role for flavonoids as endogenous regulators of auxin transport.

Study of the Chemical Composition of the Resinous Exudate Isolated from Heliotropium Sclerocarpum and Evaluation of the Antioxidant Properties of the Phenolic Compounds and the Resin

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René Torres

2009-11-01

Full Text Available Heliotropium sclerocarpum Phil. (Heliotropiaceae is a resinous bush that grows in the Atacama of northern Chile. The chemical composition of its resinous exudate was analyzed for the first time. One aromatic geranyl derivative: filifolinol (1, one flavanone: naringenin (2 and a new type of 3-oxo-2-arylbenzofuran derivative 3 were isolated and their structures were determined. The antioxidant activity of the phenolic compounds and resin was evaluated using the bleaching of DPPH radical method and expressed as fast reacting equivalents (FRE and total reacting equivalents (TRE.

Scale-up of counter-current chromatography: demonstration of predictable isocratic and quasi-continuous operating modes from the test tube to pilot/process scale.

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Sutherland, Ian; Hewitson, Peter; Ignatova, Svetlana

2009-12-11

Predictable scale-up from test tube derived distribution ratios and analytical-scale sample loading optimisation is demonstrated using a model sample system of benzyl alcohol and p-cresol in a heptane:ethyl acetate:methanol:water phase system with the new 18 L Maxi counter-current chromatography centrifuge. The versatility of having a liquid stationary phase with its high loading capacity and flexible operating modes is demonstrated at two different scales by separating and concentrating target compounds using a mixture of caffeine, vanillin, naringenin and carvone using a quasi-continuous technique called intermittent counter-current extraction.

Ion Channels Induced by Antimicrobial Agents in Model Lipid Membranes are Modulated by Plant Polyphenols Through Surrounding Lipid Media.

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Efimova, Svetlana S; Zakharova, Anastasiia A; Medvedev, Roman Ya; Ostroumova, Olga S

2018-03-16

The potential therapeutic applications of plant polyphenols in various neurological, cardiovascular, metabolic and malignant disorders determine the relevance of studying the molecular mechanisms of their action on the cell membranes. Here, the quantitative changes in the physical parameters of model bilayer lipid membranes upon the adsorption of plant polyphenols were evaluated. It was shown that butein and naringenin significantly decreased the intrinsic dipole potential of cholesterol-free and cholesterol-enriched membranes. Cardamonin, 4'-hydroxychalcone, licochalcone A and liquiritigenin demonstrated the average efficiency, while resveratrol did not characterized by the ability to modulate the bilayer electrostatics. At the same time, the tested polyphenols affected melting of phospholipids with saturated acyl chains. The effects were attributed to the lipid disordering and a promotion of the positive curvature stress. According to DSC data and results of measurements of the threshold voltages that cause bilayer breakdown licochalcone A is the most effective agent. Furthermore, the role of the polyphenol induced changes in the electric and elastic properties of lipid host in the regulation of reconstituted ion channels was examined. The ability of the tested polyphenols to decrease the conductance of single ion channels produced by the antifungal cyclic lipopeptide syringomycin E was in agreement with their effects on the dipole potential of the lipid bilayers. The greatest effect of licochalcone A on the steady-state membrane conductance induced by the antifungal polyene macrolide antibiotic nystatin correlated with its greatest efficacy to induce the positive curvature stress. We also found that butein and naringenin bind specifically to a single pore formed by α-hemolysin from Staphylococcus aureus.

Distribution and biosynthesis of flavan-3-ols in Camellia sinensis seedlings and expression of genes encoding biosynthetic enzymes.

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Ashihara, Hiroshi; Deng, Wei-Wei; Mullen, William; Crozier, Alan

2010-04-01

The distribution of phenolic compounds in young and developing leaves, stems, main and lateral roots and cotyledons of 8-week-old tea (Camellia sinensis) seedlings was investigated using HPLC-MS(2). Fourteen compounds, flavan-3-ols, chlorogenic acids, and kaempferol-O-glycosides, were identified on the basis of their retention time, absorbance spectrum, and MS fragmentation pattern. The major phenolics were (-)-epigallocatechin-3-O-gallate and (-)-epicatechin-3-O-gallate, located principally in the green parts of the seedlings. Considerable amounts of radioactivity from [ring-(14)C]phenylalanine were incorporated in (-)-epicatechin, (-)-epigallocatechin, (-)-epicatechin-3-O-gallate and (-)-epigallocatechin-3-O-gallate, by tissues of young and developing leaves and stems. Expression of genes encoding enzymes involved in flavan-3-ol biosynthesis, CHS, CHI, F3H, F3'5'H, DFR, ANS, ANR and LAR was investigated. Transcripts of all genes, except LAR, were more abundant in leaves and stems than in roots and cotyledons. No significant difference was found in the amount of transcript of LAR. These findings indicate that in tea seedlings flavan-3-ols are produced by a naringenin-chalcone-->naringenin-->dihydrokaempferol pathway. Dihydrokaempferol is a branch point in the synthesis of (-)-epigallocatechin-3-O-gallate and other flavan-3-ols which can be formed by routes beginning with either a flavonoid 3'-hydroxylase mediated conversion of the flavonol to dihydroquercetin or a flavonoid 3',5'-hydroxylase-catalysed conversion to dihydromyricetin with subsequent steps involving sequential reactions catalysed by dihydroflavanol 4-reductase, anthocyanidin synthase, anthocyanidin reductase and flavan-3-ol gallate synthase. Copyright 2010 Elsevier Ltd. All rights reserved.

Bioactive compounds from culinary herbs inhibit a molecular target for type 2 diabetes management, dipeptidyl peptidase IV.

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Bower, Allyson M; Real Hernandez, Luis M; Berhow, Mark A; de Mejia, Elvira Gonzalez

2014-07-02

Greek oregano (Origanum vulgare), marjoram (Origanum majorana), rosemary (Rosmarinus officinalis), and Mexican oregano (Lippia graveolens) are concentrated sources of bioactive compounds. The aims were to characterize and examine extracts from greenhouse-grown or commercially purchased herbs for their ability to inhibit dipeptidyl peptidase IV (DPP-IV) and protein tyrosine phosphatase 1B (PTP1B), enzymes that play a role in insulin secretion and insulin signaling, respectively. Greenhouse herbs contained more polyphenols (302.7-430.1 μg of gallic acid equivalents/mg of dry weight of extract (DWE)) and flavonoids (370.1-661.4 μg of rutin equivalents/mg of DWE) compared to the equivalent commercial herbs. Greenhouse rosemary, Mexican oregano, and marjoram extracts were the best inhibitors of DPP-IV (IC₅₀=16, 29, and 59 μM, respectively). Commercial rosemary, Mexican oregano, and marjoram were the best inhibitors of PTP1B (32.4-40.9% at 500 μM). The phytochemicals eriodictyol, naringenin, hispidulin, cirsimaritin, and carnosol were identified by LC-ESI-MS as being present in greenhouse-grown Mexican oregano and rosemary. Computational modeling indicated that hispidulin, carnosol, and eriodictyol would have the best binding affinities for DPP-IV. Biochemically, the best inhibitors of DPP-IV were cirsimaritin (IC₅₀=0.43±0.07 μM), hispidulin (IC₅₀=0.49±0.06 μM), and naringenin (IC₅₀=2.5±0.29 μM). Overall, herbs contain several flavonoids that inhibit DPP-IV and should be investigated further regarding their potential in diabetes management.

preparation and properties of immobilized naringinase in polyvinyl alcohol copolymer carrier for debittering of citrus juices

International Nuclear Information System (INIS)

ElBatal, A.L.; Swailam, H.M.H.

2003-01-01

Naringin a bitter compound in citrus can be converted to a nonbiter fom by enzyme hydrolysis. Naringinase from gamma irradiated enhanced Aspergillus nigro-AH3. γ 20 isolate was partoally purified by various methods and the specificacitivty of 6.1 units per mg protein was obtained. The enzyme was immobilized by entrapment in polyvinyl alcohol / polyacrylamide (PVA/PAAm) copolymer hydrogel carrier produced by gamma radiation polymerization. The activity of the immobilized enzyme was elevated with increasing PVA content in the copolymer carrier to reach its maximum value at PVA/PAAm composition ratio of (60.40, v/v%). The yield of immobilization was highest 95% and yield of activity was 91.1%, when 1 mg naringinase enzyme was immobilized in 1 ml of hydrogel matrix. Some enzymatic and compared with those of the solube free enzyme. The optimal pH of the immobilized enzyme was shifted 0.5 pH units to the alkaline side of that of the soluble free enzyme. Also the optimum temperature was shifted from 50 C degree to 60 c degree and the activation energy of reaction (EA) was markedly decreased from 21.52 to 10.74kcal/mol by immobilization. The influence of the diffusion is reflected in the kinetic parameters Km and Vmax. The application of kinetic parameter of the immobilized enzyme optimized with pure naringin solution and bitter orange juice resuled in about 83.2% and 72.0% debittering after 8 h and 12 h incubation during batcheise operation, respectively. The process has operational versatility from the broad pH and temperature optima and affords highest efficiency and stability during application in debittering of bitter orange juice because it is recycled consecutively 14 times before retaining only about 50 % efficiency. These data can be used for future improvements in debittering of citrus fruits products

Targeted isolation and identification of bioactive compounds lowering cholesterol in the crude extracts of crabapples using UPLC-DAD-MS-SPE/NMR based on pharmacology-guided PLS-DA.

Science.gov (United States)

Wen, Chao; Wang, Dongshan; Li, Xing; Huang, Tao; Huang, Cheng; Hu, Kaifeng

2018-02-20

The anti-hyperlipidemic effects of crude crabapple extracts derived from Malus 'Red jade', Malus hupehensis (Pamp.) Rehd. and Malus prunifolia (Willd.) Borkh. were evaluated on high-fat diet induced obese (HF DIO) mice. The results revealed that some of these extracts could lower serum cholesterol levels in HF DIO mice. The same extracts were also parallelly analyzed by LC-MS in both positive and negative ionization modes. Based on the pharmacological results, 22 LC-MS variables were identified to be correlated with the anti-hyperlipidemic effects using partial least square discriminant analysis (PLS-DA) and independent samples t-test. Further, under the guidance of the bioactivity-correlated LC-MS signals, 10 compounds were targetedly isolated and enriched using UPLC-DAD-MS-SPE and identified/elucidated by NMR together with MS/MS as citric acid(1), p-coumaric acid(2), hyperoside(3), myricetin(4), naringenin(5), quercetin(6), kaempferol(7), gentiopicroside(8), ursolic acid(9) and 8-epiloganic acid(10). Among these 10 compounds, 6 compounds, hyperoside(3), myricetin(4), naringenin(5), quercetin(6), kaempferol(7) and ursolic acid(9), were individually studied and reported to indeed have effects on lowering the serum lipid levels. These results demonstrated the efficiency of this strategy for drug discovery. In contrast to traditional routes to discover bioactive compounds in the plant extracts, targeted isolation and identification of bioactive compounds in the crude plant extracts using UPLC-DAD-MS-SPE/NMR based on pharmacology-guided PLS-DA of LC-MS data brings forward a new efficient dereplicated approach to natural products research for drug discovery. Copyright © 2017 Elsevier B.V. All rights reserved.

Polyphenol compounds of the kino of Eucalyptus citriodora

International Nuclear Information System (INIS)

Freitas, Marinalva Oliveira; Lima, Mary Anne S.; Silveira, Edilberto R.

2007-01-01

Phytochemical analysis of the kino of Eucalyptus citriodora led to the isolation of 1-O,2-O-digaloil-6-O-trans-p-cumaroil-beta-D-glucopyranoside, 1-O-trans-p-cumaroil-6-O-cinamoil-beta-D-glucopyranoside, alpha and beta 6-O-trans-p-cumaroil-D-glucopyranoside, 7-methylaromadendrin-4'-O-6 - trans-p-cumaroil-beta-Dglucopyranoside, aromadendrin, aromadendrin-7-methyl-ether, naringenin, sakuranetin, kaempferol-7-methyl-ether and galic acid. Structural elucidation of the isolated compounds was established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift correlated NMR pulse sequences ( 1 H, 1 H-COSY, HMQC, HMBC). (author)

Flavonóides e triterpenos de Baccharis pseudotenuifolia: bioatividade sobre Artemia salina

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Moreira Francisco de Paula Madeira

2003-01-01

Full Text Available The phytochemical investigation of the chloroformic and methanolic extracts of the Baccharis pseudotenuifolia led to the isolation of triterpenes, steroids and flavonoids. From chloroformic extract were isolated oleanolic acid and alpha-spinasterol while from methanolic extract were isolated the flavonoids: hispidulin, naringenin, 3'-methoxy-luteolin, apigenin, kaempferol, eriodyctiol, aromadendrin, quercetin, 3'-methoxy-quercetin, quercetin-3-O-rhamnoside and quercetin-3-O-glucoside. The structure of these compounds were identified by IR, CG/MS, ¹H and 13C NMR spectral analysis and comparison with literature. In addition, the extracts were evaluated by means of Brine Shrimp Lethality test and the highier activity was observed in the chloroformic extract.

Flavonoids in Helichrysum pamphylicum inhibit mammalian type I DNA topoisomerase.

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Topcu, Zeki; Ozturk, Bintug; Kucukoglu, Ozlem; Kilinc, Emrah

2008-01-01

DNA topoisomerases are important targets for cancer chemotherapy. We investigated the effects of a methanolic extract of Helichrysum pamphylicum on mammalian DNA topoisomerase I via in vitro plasmid supercoil relaxation assays. The extracts manifested a considerable inhibition of the enzyme's activity in a dose-dependent manner. We also performed a HPLC analysis to identify the flavonoid content of the H. pamphylicum extract and tested the identified flavonoids; luteolin, luteolin-4-glucoside, naringenin, helichrysinA and isoquercitrin, on DNA topoisomerase I activity. The measurement of the total antioxidant capacity of the flavonoid standards suggested that the topoisomerase inhibition might be correlated with the antioxidant capacity of the plant.

Bio-based synthesis of silver nanoparticles from orange waste: effects of distinct biomolecule coatings on size, morphology, and antimicrobial activity.

Science.gov (United States)

de Barros, Caio Henrique Nasi; Cruz, Guilherme Crispim Faria; Mayrink, Willian; Tasic, Ljubica

2018-01-01

Despite the numerous reports on biological syntheses of silver nanoparticles (AgNPs), little is known about the composition of their capping agents, protein corona of plant extract-mediated synthesis, and their influence on the properties of AgNPs. Here, orange ( Citrus sinensis ) waste was utilized as a source of an extract for AgNP synthesis (the protein corona composition of which was elucidated), and also as a starting material for hesperidin and nanocellulose extraction, which were used for bio-based AgNP synthesis. A comparison of the results using the two methods of synthesis is presented. AgNPs were synthesized using orange ( C. sinensis ) peel extract (Or-AgNPs) in a biological route, and using hesperidin (Hsd-AgNPs) and nanocellulose (extracted from oranges) in a green chemical route. Characterization of nanoparticles was carried out using zeta potential and hydrodynamic size measurements, transmission electron microscopy, and X-ray diffraction. Elucidation of proteins from protein corona was performed via ultra performance liquid chromatography-tandem mass spectrometer experiments. Antimicrobial activity was assessed via minimum inhibitory concentration assays against Xanthomonas axonopodis pv. citri ( Xac ), the bacterium that causes citric canker in oranges. Or-AgNPs were not completely uniform in morphology, having a size of 48.1±20.5 nm and a zeta potential of -19.0±0.4 mV. Stabilization was performed mainly by three proteins, which were identified by tandem mass spectrometry (MS/MS) experiments. Hsd-AgNPs were smaller (25.4±12.5 nm) and had uniform morphology. Nanocellulose provided a strong steric and electrostatic (-28.2±1.0 mV) stabilization to the nanoparticles. Both AgNPs presented roughly the same activity against Xac , with the minimum inhibitory concentration range between 22 and 24 μg mL -1 . Despite the fact that different capping biomolecules on AgNPs had an influence on morphology, size, and stability of AgNPs, the antibacterial

Protections of bovine serum albumin protein from damage on functionalized graphene-based electrodes by flavonoids

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Sun, Bolu [School of Pharmacy, Lanzhou University, Lanzhou 730000 (China); Gou, Yuqiang [Lanzhou Military Command Center for Disease Prevention and Control, Lanzhou 730000 (China); Xue, Zhiyuan; Zheng, Xiaoping; Ma, Yuling [School of Pharmacy, Lanzhou University, Lanzhou 730000 (China); Hu, Fangdi, E-mail: hufd@lzu.edu.cn [School of Pharmacy, Lanzhou University, Lanzhou 730000 (China); Zhao, Wanghong, E-mail: wanghongzhao@sina.com [Department of Stomatology, Nanfang Hospital, Southern Medical University, Guangzhou 51515 (China)

2016-05-01

A sensitive electrochemical sensor based on bovine serum albumin (BSA)/poly (diallyldimethylammonium chloride) (PDDA) functionalized graphene nanosheets (PDDA-G) composite film modified glassy carbon electrode (BSA/PDDA-G/GCE) had been developed to investigate the oxidative protein damage and protections of protein from damage by flavonoids. The performance of this sensor was remarkably improved due to excellent electrical conductivity, strong adsorptive ability, and large effective surface area of PDDA-G. The BSA/PDDA-G/GCE displayed the greatest degree of BSA oxidation damage at 40 min incubation time and in the pH 5.0 Fenton reagent system (12.5 mM FeSO{sub 4}, 50 mM H{sub 2}O{sub 2}). The antioxidant activities of four flavonoids had been compared by fabricated sensor based on the relative peak current ratio of SWV, because flavonoids prevented BSA damage caused by Fenton reagent and affected the BSA signal in a solution containing Co(bpy){sub 3}{sup 3+}. The sensor was characterized by cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), and scanning electron microscopy (SEM). UV–vis spectrophotometry and FTIR were also used to investigate the generation of hydroxyl radical and BSA damage, respectively. On the basis of results from electrochemical methods, the order of the antioxidant activities of flavonoids is as follows: (+)-catechin > kaempferol > apigenin > naringenin. A novel, direct SWV analytical method for detection of BSA damage and assessment of the antioxidant activities of four flavonoids was developed and this electrochemical method provided a simple, inexpensive and rapid detection of BSA damage and evaluation of the antioxidant activities of samples. - Highlights: • Hydroxyl radicals were produced by Fenton reagents. • An electrochemical bovine serum albumin (BSA) damage sensor was successfully fabricated. • The proposed biosensor can assess the antioxidant capacity of four flavonoids. • The order of antioxidant

Protections of bovine serum albumin protein from damage on functionalized graphene-based electrodes by flavonoids

International Nuclear Information System (INIS)

Sun, Bolu; Gou, Yuqiang; Xue, Zhiyuan; Zheng, Xiaoping; Ma, Yuling; Hu, Fangdi; Zhao, Wanghong

2016-01-01

A sensitive electrochemical sensor based on bovine serum albumin (BSA)/poly (diallyldimethylammonium chloride) (PDDA) functionalized graphene nanosheets (PDDA-G) composite film modified glassy carbon electrode (BSA/PDDA-G/GCE) had been developed to investigate the oxidative protein damage and protections of protein from damage by flavonoids. The performance of this sensor was remarkably improved due to excellent electrical conductivity, strong adsorptive ability, and large effective surface area of PDDA-G. The BSA/PDDA-G/GCE displayed the greatest degree of BSA oxidation damage at 40 min incubation time and in the pH 5.0 Fenton reagent system (12.5 mM FeSO_4, 50 mM H_2O_2). The antioxidant activities of four flavonoids had been compared by fabricated sensor based on the relative peak current ratio of SWV, because flavonoids prevented BSA damage caused by Fenton reagent and affected the BSA signal in a solution containing Co(bpy)_3"3"+. The sensor was characterized by cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), and scanning electron microscopy (SEM). UV–vis spectrophotometry and FTIR were also used to investigate the generation of hydroxyl radical and BSA damage, respectively. On the basis of results from electrochemical methods, the order of the antioxidant activities of flavonoids is as follows: (+)-catechin > kaempferol > apigenin > naringenin. A novel, direct SWV analytical method for detection of BSA damage and assessment of the antioxidant activities of four flavonoids was developed and this electrochemical method provided a simple, inexpensive and rapid detection of BSA damage and evaluation of the antioxidant activities of samples. - Highlights: • Hydroxyl radicals were produced by Fenton reagents. • An electrochemical bovine serum albumin (BSA) damage sensor was successfully fabricated. • The proposed biosensor can assess the antioxidant capacity of four flavonoids. • The order of antioxidant activities of flavonoids is

Composition of Essential Oils and Ethanol Extracts of the Leaves of Lippia Species: Identification, Quantitation and Antioxidant Capacity

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Maria T.S. Trevisan

2016-01-01

Full Text Available The principal components of essential oils, obtained by steam-hydrodistillation from the fresh leaves of five species of the genus Lippia, namely Lippia gracilis AV, Lippia sidoides Mart , Lippia alba carvoneifera, Lippia alba citralifera and Lippia alba myrceneifera and ethanol extracts , were evaluated. The greater antioxidant capacity (IC 50 = 980 µg/mL; p 2000 µg/mL. Major compounds in the oils were, thymol (Lippia sidoides Mart, 13.1 g/k, carvone (Lippia alba carvoneifera, 9.6 g/kg, geranial ( Lippia alba citraleifera, 4.61 g/kg; Lippiaalba myrceneifera, 1.6 g/kg, neral ( Lippia alba citraleifera, 3.4 g/kg; Lippia alba myrceneifera, 1.16 g/k, carvacrol (Lippia gracilis AV, 5.36 g/kg and limonene (Lippia alba carvoneifera, 5.14 g/kg. Of these, carvone (IC 50 = 330 µM along with thymol (1.88 units, and carvacrol (1.74 units, were highly active in the hypoxanthine/xanthine oxidase, and ORAC assays respectively. The following compounds namely I: calceolarioside E, II: acteoside, III: isoacteoside, IV: luteolin, V: 5,7,3´,4´-tetrahydroxy-3,6-dimethoxy flavone (spinacetin , VI: naringenin, VII: apigenin, VIII: 6-methoxy apigenin (hispidulin, IX: 5,7,3´-trihydroxy-3,6,4´-trimethoxy flavone , X:5,7,4´-trihydroxy-3,6-dimethoxy flavone , XI: naringenin-4´-methyl ether, XII: 5,7-dihydroxy-3,6,4´-trimethoxy flavone (santin , XIII:5,7-dihydroxy-6,4´-dimethoxy-flavone (pectolinaringenin and XIV: 5-hydroxy-3,7,4´-trimethoxy flavone were identified in the ethanol extracts . Of the leaf ethanol extracts, strong antioxidant capacity was only evident in that of Lippia alba carvoneifera (IC 50 = 1.23 mg/mL. Overall, the data indicates that use of the leaves of Lippia species in food preparations, should be beneficial to health.

Polyphenol compounds of the kino of Eucalyptus citriodora; Compostos polifenolicos do kino de Eucalyptus citriodora

Energy Technology Data Exchange (ETDEWEB)

Freitas, Marinalva Oliveira; Lima, Mary Anne S.; Silveira, Edilberto R. [Universidade Federal do Ceara (UFC), Fortaleza, CE (Brazil). Dept. de Quimica Organica e Inorganica]. E-mail: edil@ufc.br

2007-07-01

Phytochemical analysis of the kino of Eucalyptus citriodora led to the isolation of 1-O,2-O-digaloil-6-O-trans-p-cumaroil-beta-D-glucopyranoside, 1-O-trans-p-cumaroil-6-O-cinamoil-beta-D-glucopyranoside, alpha and beta 6-O-trans-p-cumaroil-D-glucopyranoside, 7-methylaromadendrin-4'-O-6{sup -}trans-p-cumaroil-beta-Dglucopyranoside, aromadendrin, aromadendrin-7-methyl-ether, naringenin, sakuranetin, kaempferol-7-methyl-ether and galic acid. Structural elucidation of the isolated compounds was established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift correlated NMR pulse sequences ({sup 1}H,{sup 1}H-COSY, HMQC, HMBC). (author)

Phenolic constituents and antioxidant activity of geopropolis from two species of amazonian stingless bees

Energy Technology Data Exchange (ETDEWEB)

Silva, Ellen Cristina Costa da; Muniz, Magno Perea; Nunomura, Rita de Cassia Saraiva, E-mail: ellensilva@yahoo.com.br [Departamento de Quimica, Instituto de Ciencias Exatas, Universidade Federal do Amazonas, Manaus, AM (Brazil); Nunomura, Sergio Massayoshi [Departamento de Produtos Naturais, Instituto Nacional de Pesquisas da Amazonia, Manaus, AM (Brazil); Zilse, Gislene Almeida Carvalho [Departamento de Biodiversidade, Instituto Nacional de Pesquisas da Amazonia, Manaus, AM (Brazil)

2013-09-01

We investigated the phenolic constituents and antioxidant activity of geopropolis from two species of stingless Amazonian bees, Melipona interrupta and Melipona seminigra. The chemical investigation of geopropolis from Melipona interrupta led to the isolation of 5,7,4'-trihydroxyflavonone, 3,5,6,7,4'-pentahydroxyflavonol, naringenine-4'-O-{beta}-D-glucopyranoside and myricetin-3-O-{beta}-D-glucopyranoside. Their structures were assigned based on spectroscopic analyses, including two-dimensional NMR techniques. Antioxidant activity of methanol and ethanol extracts of M. interrupta and M. seminigra were measured using the 1,2-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay. This is also the first work reporting the chemical investigation of stingless bee species from the Amazonian region. (author)

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

Directory of Open Access Journals (Sweden)

Viktor Ilkei

2016-11-01

Full Text Available Starting from racemic naringenin ((±-1, a mixture of dracocephin A stereoisomers 6-(2”-pyrrolidinone-5”-ylnaringenin (±-2a–d and its regioisomer, dracocephin B 8-(2”-pyrrolidinone-5”-ylnaringenin (±-3a–d originally isolated from Dracocephalum rupestre, have been synthesized in a one-pot reaction. The separation of 2a–d and 3a–d was achieved by preparative HPLC. The four stereoisomers of each natural product were separated by analytical chiral HPLC and their absolute configuration was studied by the combination of HPLC–ECD measurements and TDDFT–ECD calculations. The synthesized flavonoid alkaloids were further characterized by physicochemical and in vitro pharmacological studies.

Compostos polifenólicos do kino de Eucalyptus citriodora Polyphenol compounds of the kino of Eucalyptus citriodora

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Marinalva Oliveira Freitas

2007-01-01

Full Text Available Phytochemical analysis of the kino of Eucalyptus citriodora led to the isolation of 1-O,2-O-digaloil-6-O-trans -p-cumaroil-beta-D-glucopyranoside, 1-O-trans-p-cumaroil-6-O -cinamoil-beta-D-glucopyranoside, alpha and beta 6-O-trans-p-cumaroil-D-glucopyranoside, 7-methylaromadendrin-4'-O-6''- trans-p-cumaroil-beta-D-glucopyranoside, aromadendrin, aromadendrin-7-methyl-ether, naringenin, sakuranetin, kaempferol-7-methyl-ether and galic acid. Structural elucidation of the isolated compounds was established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift correlated NMR pulse sequences (¹H,¹H-COSY, HMQC, HMBC.

Flavonoids released by carrot (Daucus carota) seedlings stimulate hyphal development of vesicular-arbuscular mycorrhizal fungi in the presence of optimal CO2 enrichment.

Science.gov (United States)

Poulin, M J; Bel-Rhlid, R; Piché, Y; Chênevert, R

1993-10-01

Carbon dioxide has been previously identified as a critical volatile factor that stimulates hyphal growth ofGigaspora margarita, a vesiculararbuscular mycorrhizal fungus, and we determined the optimal concentration at 2.0%. The beneficial effect of CO2 on fungal development is also visible in the presence of stimulatory (quercetin, myricetin) or inhibitory (naringenin) flavonoids. Sterile root exudates from carrot seedlings stimulate the hyphal development ofG. margarita in the presence of optimal CO2 enrichment. Three flavonols (quercetin, kaempferol, rutin or quercetin 3-rutinoside) and two flavones (apigenin, luteolin) were identified in carrot root exudates by means of HPLC retention time. Flavonols like quercetin and kaempferol are known to have stimulatory effects on hyphal growth ofG. margarita.

Inhibitory effects of Citrus hassaku extract and its flavanone glycosides on melanogenesis.

Science.gov (United States)

Itoh, Kimihisa; Hirata, Noriko; Masuda, Megumi; Naruto, Shunsuke; Murata, Kazuya; Wakabayashi, Keitaro; Matsuda, Hideaki

2009-03-01

The 50% ethanolic extract (CH-ext) obtained from the unripe fruit of Citrus hassaku exhibited significant tyrosinase inhibitory activity. The CH-ext showed antioxidant activity, such as superoxide dismutase (SOD)-like activity and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity. Activity-guided fractionation of the CH-ext indicated that flavanone glycoside-rich fractions showed potent tyrosinase inhibitory activity. Further examination revealed that the tyrosinase inhibitory activity and antioxidant activity of the CH-ext were attributable to naringin and neohesperidin, respectively. The CH-ext showed inhibition of melanogenesis without any effects on cell proliferation in cultured murine B16 melanoma cells after glucosamine exposure. The topical application of the CH-ext to the dorsal skin of brownish guinea pigs showed in vivo preventive effects against UVB-induced pigmentation.

Corrosion inhibition of carbon steel in acidic medium by orange peel extract and its main antioxidant compounds

International Nuclear Information System (INIS)

M’hiri, Nouha; Veys-Renaux, Delphine; Rocca, Emmanuel; Ioannou, Irina; Boudhrioua, Nourhéne Mihoubi; Ghoul, Mohamed

2016-01-01

Highlights: • Catechol and derived functions are responsible for flavonoids antioxidant activity. • Antioxidant activity of adsorbed molecules explains cathodic inhibition. • Orange peel extract inhibition is enhanced by the precipitation of a covering film. - Abstract: Chemical compounds of orange peel extracts were identified and their antioxidant activities were determined. The inhibiting effect on acidic steel corrosion brought by the extract and selected antioxidant compounds (neohesperidin, naringin, ascorbic acid) was evaluated separately by electrochemical methods. Whatever the extract concentration, a significant inhibition is observed, whereas selected antioxidant compounds show only a slight effect. Both electrochemical impedance spectroscopy results and scanning electron microscopy observations after immersion reveal that the inhibiting efficiency of orange peel extract is not only due to the antioxidant activity of its compounds but also to the precipitation of a surface film.

Alkaloids of root barks of Zanthoxylum spp; Alcaloides das cascas das raizes de Zanthoxylum spp

Energy Technology Data Exchange (ETDEWEB)

Hohlemwerger, Sandra Virginia Alves; Sales, Edijane Matos; Costa, Rafael dos Santos; Velozo, Eudes da Silva [Universidade Federal da Bahia (UFBA), Salvador, BA (Brazil). Fac. de Farmacia. Dept. do Medicamento; Guedes, Maria Lenise da Silva, E-mail: euvelozo@ufba.br [Universidade Federal da Bahia (UFBA), Salvador, BA (Brazil). Inst. de Biologia Herbario Alexandre Leal Costa

2012-07-01

In 1959, Gottlieb and Antonaccio published a study reporting the occurrence of lignan sesamin and triterpene lupeol in Zanthoxylum tingoassuiba. In this work we describe the phytochemical study of the root bark of the Z. tingoassuiba which allowed the identification of the lupeol, sesamin, and alkaloids dihydrochelerythrine, chelerythrine, anorttianamide, cis-N-methyl-canadin, predicentine, 2, 3-methylenedioxy-10,11-dimethoxy-tetrahydro protoberberine. The investigation of hexane and methanol extracts of the root bark of Z. rhoifolium and Z. stelligerum also investigated showed the presence of alkaloids dihydrochelerythrine, anorttianamide, cis-N-methyl-canadine, 7,9-dimethoxy-2,3- methylenedioxybenzophen anthridine and angoline. The occurrence of 2,3-methylenedioxy-10,11-dimethoxy-tetrahydro protoberberine is first described in Z. tingoassuiba and Z. stelligerum. This is also the first report of the presence of hesperidin and neohesperidin in roots of Z. stelligerum (author)

Phenolic compounds and biological effects of edible Rumex scutatus and Pseudosempervivum sempervivum: potential sources of natural agents with health benefits.

Science.gov (United States)

Savran, Ahmet; Zengin, Gokhan; Aktumsek, Abdurrahman; Mocan, Andrei; Glamoćlija, Jasmina; Ćirić, Ana; Soković, Marina

2016-07-13

The present study outlines a chemical characterization and further effects beneficial to health of edible Rumex scutatus and Pseudosempervivum sempervivum, in addition to presenting the antioxidant, enzyme inhibitory effects and antimicrobial properties of different extracts. The phenolic compounds composition of the extracts was assessed by RP-HPLC-DAD, outlining benzoic acid and rutin as major constituents in P. sempervivum and rutin and hesperidin in R. scutatus. Moreover, further biological effects were tested on key enzymes involved in diabetes mellitus, Alzheimer's disease and skin melanogenesis revealing an important tyrosinase inhibitory effect of Pseudosempervivum water extract. Moreover, both species possessed antimicrobial properties towards bacteria and fungi relevant to public health. Accordingly, we find that R. scutatus and P. sempervivum can be considered as novel functional foods because they are rich sources of biologically active compounds that provide health benefits.

Alkaloids of root barks of Zanthoxylum spp

International Nuclear Information System (INIS)

Hohlemwerger, Sandra Virginia Alves; Sales, Edijane Matos; Costa, Rafael dos Santos; Velozo, Eudes da Silva; Guedes, Maria Lenise da Silva

2012-01-01

In 1959, Gottlieb and Antonaccio published a study reporting the occurrence of lignan sesamin and triterpene lupeol in Zanthoxylum tingoassuiba. In this work we describe the phytochemical study of the root bark of the Z. tingoassuiba which allowed the identification of the lupeol, sesamin, and alkaloids dihydrochelerythrine, chelerythrine, anorttianamide, cis-N-methyl-canadin, predicentine, 2, 3-methylenedioxy-10,11-dimethoxy-tetrahydro protoberberine. The investigation of hexane and methanol extracts of the root bark of Z. rhoifolium and Z. stelligerum also investigated showed the presence of alkaloids dihydrochelerythrine, anorttianamide, cis-N-methyl-canadine, 7,9-dimethoxy-2,3- methylenedioxybenzophen anthridine and angoline. The occurrence of 2,3-methylenedioxy-10,11-dimethoxy-tetrahydro protoberberine is first described in Z. tingoassuiba and Z. stelligerum. This is also the first report of the presence of hesperidin and neohesperidin in roots of Z. stelligerum (author)

Composition and Antioxidant Activity of Geopropolis Collected by Melipona subnitida (Jandaíra) Bees.

Science.gov (United States)

Alves de Souza, Silvana; Camara, Celso Amorim; Monica Sarmento da Silva, Eva; Silva, Tania Maria Sarmento

2013-01-01

An investigation of the geopropolis collected by Melipona subnitida (jandaíra) stingless bee led to the isolation and characterization of two phenylpropanoids, 6-O-p-coumaroyl-D-galactopyranose (1) and 6-O-cinnamoyl-1-O-p-coumaroyl- β -D-glucopyranose (2), and seven flavonoids, 7-O-methyl-naringenin (3), 7-O-methyl aromadendrin (4), 7,4'-di-O-methyl aromadendrin (5), 4'-O-methyl kaempferol (6), 3-O-methyl quercetin (7), 5-O-methyl aromadendrin (8), and 5-O-methyl kaempferol (9). The structure of the new phenylpropanoid (1) was established from IR, LC-ESI-MS, and NMR spectral data, including 2D NMR experiments. The extract and fractions demonstrated significant antioxidant activity in DPPH, ABTS, and β -carotene/linoleic acid tests.

Phenolic constituents and antioxidant activity of geopropolis from two species of amazonian stingless bees

International Nuclear Information System (INIS)

Silva, Ellen Cristina Costa da; Muniz, Magno Perêa; Nunomura, Rita de Cássia Saraiva; Nunomura, Sergio Massayoshi; Zilse, Gislene Almeida Carvalho

2013-01-01

We investigated the phenolic constituents and antioxidant activity of geopropolis from two species of stingless Amazonian bees, Melipona interrupta and Melipona seminigra. The chemical investigation of geopropolis from Melipona interrupta led to the isolation of 5,7,4’-trihydroxyflavonone, 3,5,6,7,4’-pentahydroxyflavonol, naringenine-4’-O-β-D-glucopyranoside and myricetin-3-O-β-D-glucopyranoside. Their structures were assigned based on spectroscopic analyses, including two-dimensional NMR techniques. Antioxidant activity of methanol and ethanol extracts of M. interrupta and M. seminigra were measured using the 1,2-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay. This is also the first work reporting the chemical investigation of stingless bee species from the Amazonian region. (author)

Flavonoids and other substances of Lippia sidoids and its antioxidant activities

International Nuclear Information System (INIS)

Almeida, Macia Cleane S. de; Alves, Leonardo A.; Souza, Luciana Gregorio da S.; Machado, Luciana L.; Matos, Marcos C. de; Oliveira, Maria Conceicao F. de; Lemos, Telma L.G.

2010-01-01

The chemical investigation of the ethanol extracts of stems, roots and leaves of Lippia sidoides led to the isolation of: steroid β-sitosterol, naphthoquinone tecomaquinone, monoterpene carvacrol, flavonoid 4',5,7-trihydroxyflavanone (naringenin), 3',4',5,7-tetrahydroxyflavanone and 4',5,7-trihydroxy-6-methoxyflavone flavonoids mixture, and 3,4,4',6'-tetrahydroxydihydrochalcone-2'-O-b-D-glucopyranoside and 4,4',6'-trihydroxydihydrochalcone-2'-O- b-D-glucopyranoside dihydrochalcones mixture. Their structures were characterized on the basis of spectral data, mainly 1 H and 13 C NMR (1D and 2D) and mass spectra. The ethanol extract and isolated compounds were evaluated for their antioxidative properties using the method of inhibition of free radical DPPH (2,2-diphenyl-1-picrylhydrazyl). (author)

Constituintes fenólicos e atividade antioxidante da geoprópolis de duas espécies de abelhas sem ferrão amazônicas

Directory of Open Access Journals (Sweden)

Ellen Cristina Costa da Silva

2013-01-01

Full Text Available We investigated the phenolic constituents and antioxidant activity of geopropolis from two species of stingless Amazonian bees, Melipona interrupta and Melipona seminigra. The chemical investigation of geopropolis from Melipona interrupta led to the isolation of 5,7,4'-trihydroxyflavonone, 3,5,6,7,4'-pentahydroxyflavonol, naringenine-4'-O-b-D-glucopyranoside and myricetin-3-O-b-D-glucopyranoside. Their structures were assigned based on spectroscopic analyses, including two-dimensional NMR techniques. Antioxidant activity of methanol and ethanol extracts of M. interrupta and M. seminigra were measured using the 1,2-diphenyl-2-picryl-hydrazyl (DPPH free radical scavenging assay. This is also the first work reporting the chemical investigation of stingless bee species from the Amazonian region.

Antiartherosclerotic Effects of Plant Flavonoids

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Shamala Salvamani

2014-01-01

Full Text Available Atherosclerosis is the process of hardening and narrowing the arteries. Atherosclerosis is generally associated with cardiovascular diseases such as strokes, heart attacks, and peripheral vascular diseases. Since the usage of the synthetic drug, statins, leads to various side effects, the plants flavonoids with antiartherosclerotic activity gained much attention and were proven to reduce the risk of atherosclerosis in vitro and in vivo based on different animal models. The flavonoids compounds also exhibit lipid lowering effects and anti-inflammatory and antiatherogenic properties. The future development of flavonoids-based drugs is believed to provide significant effects on atherosclerosis and its related diseases. This paper discusses the antiatherosclerotic effects of selected plant flavonoids such as quercetin, kaempferol, myricetin, rutin, naringenin, catechin, fisetin, and gossypetin.

Medicinal flowers. XXVII. New flavanone and chalcone glycosides, arenariumosides I, II, III, and IV, and tumor necrosis factor-alpha inhibitors from everlasting, flowers of Helichrysum arenarium.

Science.gov (United States)

Morikawa, Toshio; Wang, Li-Bo; Nakamura, Seikou; Ninomiya, Kiyofumi; Yokoyama, Eri; Matsuda, Hisashi; Muraoka, Osamu; Wu, Li-Jun; Yoshikawa, Masayuki

2009-04-01

The methanolic extract from the flowers of Helichrysum arenarium L. MOENCH was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha, 1 ng/ml)-induced cytotoxicity in L929 cells. From the methanolic extract, 50 constituents including four new flavanone and chalcone glycosides named arenariumosides I (1), II (2), III (3), and IV (4) were isolated. The stereostructures of 1-4 were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, naringenin 7-O-beta-D-glucopyranoside (7), apigenin 7-O-beta-D-glucopyranoside (14), apigenin 7-O-gentiobioside (16), and apigenin 7,4'-di-O-beta-D-glucopyranoside (17) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 30 microM.

Phenolic constituents and antioxidant activity of geopropolis from two species of amazonian stingless bees

Energy Technology Data Exchange (ETDEWEB)

Silva, Ellen Cristina Costa da; Muniz, Magno Perea; Nunomura, Rita de Cassia Saraiva, E-mail: ellensilva@yahoo.com.br [Departamento de Quimica, Instituto de Ciencias Exatas, Universidade Federal do Amazonas, Manaus, AM (Brazil); Nunomura, Sergio Massayoshi [Departamento de Produtos Naturais, Instituto Nacional de Pesquisas da Amazonia, Manaus, AM (Brazil); Zilse, Gislene Almeida Carvalho [Departamento de Biodiversidade, Instituto Nacional de Pesquisas da Amazonia, Manaus, AM (Brazil)

2013-09-01

We investigated the phenolic constituents and antioxidant activity of geopropolis from two species of stingless Amazonian bees, Melipona interrupta and Melipona seminigra. The chemical investigation of geopropolis from Melipona interrupta led to the isolation of 5,7,4'-trihydroxyflavonone, 3,5,6,7,4'-pentahydroxyflavonol, naringenine-4'-O-{beta}-D-glucopyranoside and myricetin-3-O-{beta}-D-glucopyranoside. Their structures were assigned based on spectroscopic analyses, including two-dimensional NMR techniques. Antioxidant activity of methanol and ethanol extracts of M. interrupta and M. seminigra were measured using the 1,2-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay. This is also the first work reporting the chemical investigation of stingless bee species from the Amazonian region. (author)

Bio-based synthesis of silver nanoparticles from orange waste: effects of distinct biomolecule coatings on size, morphology, and antimicrobial activity

Science.gov (United States)

de Barros, Caio Henrique Nasi; Cruz, Guilherme Crispim Faria; Mayrink, Willian; Tasic, Ljubica

2018-01-01

Purpose Despite the numerous reports on biological syntheses of silver nanoparticles (AgNPs), little is known about the composition of their capping agents, protein corona of plant extract-mediated synthesis, and their influence on the properties of AgNPs. Here, orange (Citrus sinensis) waste was utilized as a source of an extract for AgNP synthesis (the protein corona composition of which was elucidated), and also as a starting material for hesperidin and nanocellulose extraction, which were used for bio-based AgNP synthesis. A comparison of the results using the two methods of synthesis is presented. Methods AgNPs were synthesized using orange (C. sinensis) peel extract (Or-AgNPs) in a biological route, and using hesperidin (Hsd-AgNPs) and nanocellulose (extracted from oranges) in a green chemical route. Characterization of nanoparticles was carried out using zeta potential and hydrodynamic size measurements, transmission electron microscopy, and X-ray diffraction. Elucidation of proteins from protein corona was performed via ultra performance liquid chromatography-tandem mass spectrometer experiments. Antimicrobial activity was assessed via minimum inhibitory concentration assays against Xanthomonas axonopodis pv. citri (Xac), the bacterium that causes citric canker in oranges. Results Or-AgNPs were not completely uniform in morphology, having a size of 48.1±20.5 nm and a zeta potential of −19.0±0.4 mV. Stabilization was performed mainly by three proteins, which were identified by tandem mass spectrometry (MS/MS) experiments. Hsd-AgNPs were smaller (25.4±12.5 nm) and had uniform morphology. Nanocellulose provided a strong steric and electrostatic (−28.2±1.0 mV) stabilization to the nanoparticles. Both AgNPs presented roughly the same activity against Xac, with the minimum inhibitory concentration range between 22 and 24 μg mL−1. Conclusion Despite the fact that different capping biomolecules on AgNPs had an influence on morphology, size, and stability

Cold pressed versus refined winterized corn oils: quality, composition and aroma

International Nuclear Information System (INIS)

Aydeniz Güneşer, B.; Yılmaz, E.; Ok, S.

2017-01-01

The aims of this study were to characterize and compare cold pressed and fully refined winterized corn oils. Free fatty acidity (FFA), peroxide (PV) and p-anisidin (p-AV) values, saponification number, total carotenoid and phenolic contents of cold pressed corn oils were higher than that of the refined winterized corn oils. Linoleic and oleic acids (approximately 53-54% and 30-31%, respectively) were detected as the major fatty acids in both oil samples. Fifteen different sterols with a majority of β-sitosterol, campesterol, and stigmasterol were quantified in both oil samples. Although phenolic compounds were not quantified in the refined winterized oil samples, some flavonoids (hesperidin, rutin) and phenolic acids (gallic, syringic, rosmaniric and trans-ferulic) were detected in the cold pressed oil samples. This study concludes that cold pressed corn oils could be superior in terms of bioactive compounds but still need some quality improvements for sensory attributes. [es

Thorough investigation of the oxygen heterocyclic fraction of lime (Citrus aurantifolia (Christm.) Swingle) juice.

Science.gov (United States)

Costa, Rosaria; Russo, Marina; De Grazia, Selenia; Grasso, Elisa; Dugo, Paola; Mondello, Luigi

2014-04-01

Reversed-phase-HPLC analysis by means of superficially porous silica particle columns (fused-core) was applied to the investigation of flavonoids, coumarins, and psoralens in lime juice samples. Hesperidin (367.0 ± 16.0 ppm) and eriocitrin (148.0 ± 7.9 ppm) were the most abundant flavonoids. Fifteen coumarins and furocoumarins were determined, including bergamottin (29.6 ± 1.1 ppm), 5-geranyloxy-7-methoxycoumarin (16.5 ± 0.6 ppm), and oxypeucedanin hydrate (9.9 ± 0.5 ppm) as predominant compounds. These molecules are today well known for their beneficial effects on human health. As a consequence, the present study, beyond investigating for the first time the chemical composition of lime juice, highlights also its health-promoting qualities, due to its content of flavonoids and coumarins. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Operational stability of naringinase PVA lens-shaped microparticles in batch stirred reactors and mini packed bed reactors-one step closer to industry.

Science.gov (United States)

Nunes, Mário A P; Rosa, M Emilia; Fernandes, Pedro C B; Ribeiro, Maria H L

2014-07-01

The immobilization of naringinase in PVA lens-shaped particles, a cheap and biocompatible hydrogel was shown to provide an effective biocatalyst for naringin hydrolysis, an appealing reaction in the food and pharmaceutical industries. The present work addresses the operational stability and scale-up of the bioconversion system, in various types of reactors, namely shaken microtiter plates (volume ⩽ 2 mL), batch stirred tank reactors (volume reactor (PBR, 6.8 mL). Consecutive batch runs were performed with the shaken/stirred vessels, with reproducible and encouraging results, related to operational stability. The PBR was used to establish the feasibility for continuous operation, running continuously for 54 days at 45°C. The biocatalyst activity remained constant for 40 days of continuous operation. The averaged specific productivity was 9.07 mmol h(-1) g enzyme(-1) and the half-life of 48 days. Copyright © 2014 Elsevier Ltd. All rights reserved.

Composition and Antioxidant Activity of Geopropolis Collected by Melipona subnitida (Jandaíra Bees

Directory of Open Access Journals (Sweden)

Silvana Alves de Souza

2013-01-01

Full Text Available An investigation of the geopropolis collected by Melipona subnitida (jandaíra stingless bee led to the isolation and characterization of two phenylpropanoids, 6-O-p-coumaroyl-D-galactopyranose (1 and 6-O-cinnamoyl-1-O-p-coumaroyl-β-D-glucopyranose (2, and seven flavonoids, 7-O-methyl-naringenin (3, 7-O-methyl aromadendrin (4, 7,4′-di-O-methyl aromadendrin (5, 4′-O-methyl kaempferol (6, 3-O-methyl quercetin (7, 5-O-methyl aromadendrin (8, and 5-O-methyl kaempferol (9. The structure of the new phenylpropanoid (1 was established from IR, LC-ESI-MS, and NMR spectral data, including 2D NMR experiments. The extract and fractions demonstrated significant antioxidant activity in DPPH, ABTS, and β-carotene/linoleic acid tests.

Flavonoids in human urine as biomarkers for intake of fruits and vegetables

DEFF Research Database (Denmark)

Nielsen, Salka E.; Freese, R.; Kleemola, P.

2002-01-01

Flavonoids are polyphenolic compounds ubiquitously found in human diets. We have studied the association between urinary excretion of flavonoids and the intake of fruits and vegetables to evaluate the usefulness of flavonoids as a biomarker for fruit and vegetable intake. Levels of 12 dietary...... relevant flavonoids were determined by LC-MS in urine samples collected prior to an intervention study, when the subjects were on their habitual diet (n = 94), and after they had participated in an intervention study with diets either high or low in fruits, berries, and vegetables (n = 77). Both flavonoid...... glycosides and aglycones were included in the assay, but only the flavonoid aglycones were detectable. Thus, the flavonols quercetin, kaempferol, isorhamnetin, and tamarixetin, the dihydrochalcone phloretin, and the flavanones naringenin and hesperetin were quantified in the enzymatically hydrolyzed urine...

Flavonoids and other substances of Lippia sidoids and its antioxidant activities; Flavonoides e outras substancias de Lippia sidoides e suas atividades antioxidantes

Energy Technology Data Exchange (ETDEWEB)

Almeida, Macia Cleane S. de; Alves, Leonardo A.; Souza, Luciana Gregorio da S.; Machado, Luciana L.; Matos, Marcos C. de; Oliveira, Maria Conceicao F. de; Lemos, Telma L.G., E-mail: tlemos@dqoi.ufc.b [Universidade Federal do Ceara (UFC), Fortaleza, CE (Brazil). Dept. de Quimica Organica e Inorganica; Braz Filho, Raimundo [Fundacao de Amparo a Pesquisa do Estado do Rio de Janeiro (FAPERJ), Rio de Janeiro, RJ (Brazil)

2010-07-01

The chemical investigation of the ethanol extracts of stems, roots and leaves of Lippia sidoides led to the isolation of: steroid {beta}-sitosterol, naphthoquinone tecomaquinone, monoterpene carvacrol, flavonoid 4',5,7-trihydroxyflavanone (naringenin), 3',4',5,7-tetrahydroxyflavanone and 4',5,7-trihydroxy-6-methoxyflavone flavonoids mixture, and 3,4,4',6'-tetrahydroxydihydrochalcone-2'-O-b-D-glucopyranoside and 4,4',6'-trihydroxydihydrochalcone-2'-O- b-D-glucopyranoside dihydrochalcones mixture. Their structures were characterized on the basis of spectral data, mainly {sup 1}H and {sup 13}C NMR (1D and 2D) and mass spectra. The ethanol extract and isolated compounds were evaluated for their antioxidative properties using the method of inhibition of free radical DPPH (2,2-diphenyl-1-picrylhydrazyl). (author)

Simultaneous determination of active ingredients in Erigeron breviscapus (Vant.) Hand-Mazz. by capillary electrophoresis with electrochemical detection.

Science.gov (United States)

Chu, Qingcui; Wu, Ting; Fu, Liang; Ye, Jiannong

2005-03-09

A high-performance capillary electrophoresis (CE) with electrochemical detection (ED) method was developed for the determination of the pharmacologically active ingredients in Erigeron breviscapus (Vant.) Hand-Mazz. and its extract phytopharmaceuticals in this work. Under the optimum conditions, nine analytes, baicalein, naringenin, scopoletin, kaempferol, apigenin, scutellarin, luteolin, caffeic acid and protocatechuic acid were separated within 24 min in a borax buffer (pH 8.7). Notably, excellent linearity was obtained over two orders of magnitude with detection limits (S/N=3) ranged from 1.0 x 10(-7) g/mL to 5.6 x 10(-7) g/mL for all nine analytes. This method was successfully used in the analysis of E. breviscapus (Vant.) Hand-Mazz. and its phytopharmaceuticals with a relatively simple extraction procedure, and the assay results were satisfactory.

Free fruit at workplace intervention increases total fruit intake: a validation study using 24 h dietary recall and urinary flavonoid excretion

DEFF Research Database (Denmark)

Krogholm, Kirstine Suszkiewicz; Bredsdorff, Lea; Alinia, Sevil

2010-01-01

, isorhamnetin, tamarixetin, kaempferol, hesperetin, naringenin, eriodictyol, daidzein, genistein, and phloretin, were measured using HPLC-electrospray ionization-MS. Results: The 24 h urinary excretion of total flavonoids and the estimated intake of fruits were significantly correlated (r(s) = 0.31, P......Background/Objectives: To validate 24 h dietary recall of fruit intake by measuring the total 24 h excretion of 10 different flavonoids in 24 h urine during an intervention with free fruit at workplaces. Subjects/Methods: Employees at workplaces offering a free-fruit program, consisting of daily...... free and easy access to fresh fruit, and controls employees at workplaces with no free-fruit program were enrolled in this validation study (n = 103). Dietary intake was assessed by using a 24 h dietary recall questionnaire at baseline and approximately 5 months later. Ten flavonoids, quercetin...

DNA fingerprinting, biological and chemical investigation of certain Yucca species.

Science.gov (United States)

El Hawary, Seham; El Sayed, Abeer; Helmy, Maged W; El Naggar, El Moataz Bellah; Marzouk, Hanan S; Bassam, Samar M

2018-01-05

Yucca aloifolia, Y. aloifolia variegata, Y. elephantipes and Y. filamentosa were investigated. DNA sequencing was performed for the four plants and a genomic DNA fingerprint was obtained and provided. The cytotoxic activities against four human cancer cell lines were investigated. The ethanolic extracts of leaves of Y. aloifolia variegata prevailed, especially against liver cancer HepG-2 and breast cancer MCF-7. In vivo assessment of hepatoprotective activity in rats also revealed the hepatoprotective potential of the ethanolic extracts of the four plants against CCl 4 - induced rats' liver damage. Qualitative and quantitative analysis of the flavonoid and phenolic content of the promising species was performed using HPLC. The analysis identified and quantified 18 flavonoids and 19 phenolic acids in the different fractions of Y. aloifolia variegata, among which the major flavonoids were hesperidin and kaemp-3-(2-p-coumaroyl) glucose and the major phenolic acids were gallic acid and protocatechuic acid.

Chemical composition and antioxidant and antifungal properties of Mentha x piperita L. (peppermint and Mentha arvensis L. (cornmint samples

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Nilo, M.C.S.,

2017-07-01

Full Text Available Essential oils and infusions from commercial peppermint sachets (CPS, and non-commercial genuine peppermint (NCP and cornmint (NCC samples were analyzed by GC/MS and LC/MS. Minimum inhibitory concentration (MIC of mint oils against Fusarium moniliforme, Aspergillus niger and Aspergillus fumigates was determined. Antioxidant potential was monitored by total phenolic content (TPC, 2,2-diphenyl-1-picrylhydrazyl (DPPH radical and soybean oil oxidation tests. CPS and NCC oils had lower menthofuran content than NCP. Mint oils did not show a uniform standard of antifungal activity and they had the modest reducing ability. CPS and NCC infusions showed higher IC50 and lower TPC than NCP ones. In the soybean oxidation test, mint oils presented prooxidant behavior. CPS infusions showed antioxidant potential significantly (P<0.05, Tukey lower than that from NCC and NCP infusions. NCP infusions were more efficient in delaying propagation reaction than NCC ones. This may be attributed to higher amount of rosmarinic acid and hesperidin in NCP.

Effect of Pasteurization on Flavonoids and Carotenoids in Citrus sinensis (L.) Osbeck cv. 'Cara Cara' and 'Bahia' Juices.

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Brasili, Elisa; Chaves, Daniela F Seixas; Xavier, Ana Augusta O; Mercadante, Adriana Z; Hassimotto, Neuza M A; Lajolo, Franco M

2017-02-22

Orange juice is considered an excellent dietary source of several bioactive compounds with beneficial properties for human health. Citrus sinensis Osbeck cv. 'Cara Cara' is a bud mutation originated from 'Washington' navel orange, also known as 'Bahia' navel orange. The ascorbic acid, flavonoid, and carotenoid contents in pasteurized and nonpasteurized Bahia and Cara Cara juices using two LC-MS/MS platforms were investigated. Higher ascorbic acid content was observed in Bahia compared to Cara Cara in both pasteurized and nonpasteurized juices. Total flavanones content as well as hesperidin levels were higher in Cara Cara with respect to Bahia pasteurized juice. Cara Cara was also characterized by a significantly higher and diversified carotenoid content compared to Bahia juice with a mixture of (Z)-isomers of lycopene, all-E-β-carotene, phytoene, and phytofluene isomers accounting for the highest carotenoid proportion. The exceptionally high carotenoid content of Cara Cara may be particularly interesting for nutritional or functional studies of uncommon carotenes in a citrus food matrix.

Composition of phenolic compounds and antioxidant attributes of Cyclea gracillima Diels extracts

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Jau-Tien Lin

2018-01-01

Full Text Available Cyclea gracillima Diels is a Taiwanese native medicinal herb. However, there are currently few relevant reports on its biochemical activity. In this study, the antioxidant attributes of the ethanol and hot water extracts of this herb were assayed using in vitro models, including the following: 2,2-diphenyl-1-(2,4,6-trinitrophenyl-hydrazyl radical scavenging, Trolox equivalent antioxidant capacity, reducing power, and chelating ferrous ions. The following biochemical models were also assayed: inhibition of human low density lipoprotein oxidation, inhibition of human erythrocyte hemolysis, and scavenging oxygen radicals in human blood. The composition and content of flavonoids and phenolic acids in these extracts were also analyzed. The results showed that these extracts with high polyphenol levels presented remarkable antioxidant effects in all assays, especially when extracted with ethanol. Six phenolic acids (mainly ferulic acid, sinapic acid, and syringic acid and 12 flavonoids (mainly narigenin, myricetin, naringin, and apigenin were found in these extracts.

Evaluation of the nutraceutical, antioxidant and cytoprotective properties of ripe pistachio (Pistacia vera L., variety Bronte) hulls.

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Barreca, Davide; Laganà, Giuseppina; Leuzzi, Ugo; Smeriglio, Antonella; Trombetta, Domenico; Bellocco, Ersilia

2016-04-01

Every year tons of pistachio hulls are separated and eliminated, as waste products, from pistachio seeds. In this study the hulls of ripe pistachios were extracted with two organic solvents (ethanol and methanol) and characterized for phenolic composition, antioxidant power and cytoprotective activity. RP-HPLC-DAD-FLU separation enabled us to identify 20 derivatives, including and by far the most abundant gallic acid, 4-hydroxybenzoic acid, protocatechuic acid, naringin, eriodictyol-7-O-glucoside, isorhamnetin-7-O-glucoside, quercetin-3-O-rutinoside, isorhamnetin-3-O-glucoside and catechin. Methanol extraction gave the highest yields for all classes of compounds and presented a higher scavenging activity in all the antioxidant assays performed. The same was found for cytoprotective activity on lymphocytes, lipid peroxidation and protein degradation. These findings highlight the strong antioxidant and cytoprotective activity of the extract components, and illustrate how a waste product can be used as a source of nutraceuticals to employ in manufacturing industry. Copyright © 2015 Elsevier Ltd. All rights reserved.

Naturally occurring compounds affect glutamatergic neurotransmission in rat brain.

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Martini, Lucia Helena; Jung, Fernanda; Soares, Felix Antunes; Rotta, Liane Nanci; Vendite, Deusa Aparecida; Frizzo, Marcos Emilio dos Santos; Yunes, Rosendo A; Calixto, João Batista; Wofchuk, Susana; Souza, Diogo O

2007-11-01

Natural products, including those derived from plants, have largely contributed to the development of therapeutic drugs. Glutamate is the main excitatory neurotransmitter in the central nervous system and it is also considered a nociceptive neurotransmitter, by acting on peripheral nervous system. For this reason, in this study we investigated the effects of the hydroalcoholic extracts from Drymis winteri (polygodial and drimanial), Phyllanthus (rutin and quercetine), Jathopha elliptica (jatrophone), Hedyosmum brasiliense (13HDS), Ocotea suaveolens (Tormentic acid), Protium kleinii (alphabeta-amyrin), Citrus paradise (naringin), soybean (genistein) and Crataeva nurvala (lupeol), described as having antinociceptive effects, on glutamatergic transmission parameters, such as [(3)H]glutamate binding, [(3)H]glutamate uptake by synaptic vesicles and astrocyte cultures, and synaptosomal [(3)H]glutamate release. All the glutamatergic parameters were affected by one or more of these compounds. Specifically, drimanial and polygodial presented more broad and profound effects, requiring more investigation on their mechanisms. The putative central side effects of these compounds, via the glutamatergic system, are discussed.

Application of transglycosylated stevia and hesperidin as drug carriers to enhance biopharmaceutical properties of poorly-soluble artemisinin.

Science.gov (United States)

Letchmanan, Kumaran; Shen, Shou-Cang; Ng, Wai Kiong; Tan, Reginald B H

2018-01-01

Biopharmaceutical properties of poorly water-soluble antimalarial drug, Artemisinin (ART), were improved by formulating amorphous solid dispersions with transglycosylated food additives (Hsp-G and Stevia-G) via co-spray drying. Both the formulated ART/Hsp-G and ART/Stevia-G showed superior dissolution properties with a burst release of more than 95% of drug within 5 min, whereas untreated ART dissolved only 4% in 5min. The supersaturation solubility of the formulated ART was enhanced by 2-fold as compared with untreated counterpart. The storage stability tests indicated that these formulations chemically stable at room temperature and under low humidity (water-soluble ART. Copyright © 2017 Elsevier B.V. All rights reserved.

Deterrent activity of hops flavonoids and their derivatives against stored product pests.

Science.gov (United States)

Jackowski, J; Popłoński, J; Twardowska, K; Magiera-Dulewicz, J; Hurej, M; Huszcza, E

2017-10-01

Five flavonoids from hops, two of their derivatives, along with naringenin used as a model compound, were tested for their antifeedant activity against three coleopteran stored product pests: Sitophilus granarius L., Tribolium confusum Duv. and Trogoderma granarium Everts. The introduction, into the tested flavonoid molecules, of additional structural fragments such as prenyl or dimethylpyran moiety, is proposed to significantly alter the deterrent activity of the compounds. The prenyl moiety in flavonoids increased the deterrent activity of these compounds in all three of the grain feeding species used in the tests. It is also concluded that the introduction of dimethylpyran moiety to the flavonoid structure increases its deterrent activity in S. granarius and T. confusum, but in one of the test insects, T. granarium, an increased feeding was observed in response to the introduction of dimethylpyran moiety to the flavonoid structure.

Differential effects of dietary flavonoids on drug metabolizing and antioxidant enzymes in female rat

DEFF Research Database (Denmark)

Breinholt, V.; Lauridsen, S.T.; Dragsted, L.O.

1999-01-01

1. Gavage administration of the natural flavonoids tangeretin, chrysin, apigenin, naringenin, genistein and quercetin for 2 consecutive weeks to the female rat resulted in differential effects on selected phase 1 and 2 enzymes in liver, colon and heart as well as antioxidant enzymes in red brood......) significantly protected against, 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP)-induced oxidative stress. Hepatic PhIP-DNA adduct formation was not affected by any of the administered flavonoids, whereas PhIP-DNA adduct formation in colon was slightly, but significantly, inhibited by quercetin......, genistein, tangeretin and BNF. 5. The observed effects of chrysin, quercetin and genistein on antioxidant enzymes, concurrently with a protection against oxidative stress, suggest a feedback mechanism on the antioxidant enzymes triggered by the flavonoid antioxidants. 6. Despite the use of high flavonoid...

In vitro biotransformation of flavonoids by rat liver microsomes

DEFF Research Database (Denmark)

Nielsen, S. E.; Breinholt, V.; Justesen, U.

1998-01-01

1. Sixteen naturally occurring flavonoids were investigated as substrates for cytochrome P450 in uninduced and Aroclor 1254-induced rat liver microsomes. Naringenin, hesperetin, chrysin, apigenin, tangeretin, kaempferol, galangin and tamarixetin were all metabolized extensively by induced rat liver...... pathway leading to the corresponding 3',4'-dihydroxylated flavonoids either by hydroxylation or demethylation. Structural requirements for microsomal hydroxylation appeared to be a single or no hydroxy group on the B-ring of the flavan nucleus. The presence of two or more hydroxy groups on the B......-ring seemed to prevent further hydroxylation. The results indicate that demethylation only occurs in the B-ring when the methoxy group is positioned at C-4'-, and not at the C-3'-position. 3. The CYP1A isozymes were found to be the main enzymes involved in flavonoid hydroxylation, whereas other cytochrome P...

In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids

DEFF Research Database (Denmark)

Breinholt, Vibeke; Offord, E.A.; Brouwer, C.

2002-01-01

Human and mouse liver microsomes And membranes isolated from Escherichia coli, which expressed cytochrome P450 (CYP) 1A2, 3A4 2C9 or 2D6, were used to investigate CYP-mediated metabolism of five selected dietary flavonoids. In human and mouse liver microsomes kaempferol, apigenin and naringenin...... were hydroxylated at the 3'-position to yield their corresponding analogs quercetin, luteolin and eriodietyol, whereas hesperetin and tamarixetin were demethylated at the 4'-position to yield eriodictyol and quercetin. respectively, Microsomal flavonoid metabolism as potently inhibited by the CYP1A2...... inhibitors. fluvoxamine and alpha-naphthoflavone. Recombinant CYP1A2 as capable of metabolizing all five investigated flavonoids. CYP3A4 recombinant protein did not catalyze hesperetin demethylation. but showed similar metabolic profiles for the remaining compounds, as did human microsomes and recombinant...

Gamma radiation induced enhancement in the antioxidant and radioprotective activities of flavonoids

International Nuclear Information System (INIS)

Arul Anantha Kumar, A.; Sonwani, Swetha; Bakkiam, D.

2018-01-01

Recently γ-radiation has been used as a tool to induce structural changes in natural biomolecules to enhance their biological and physiological properties. Flavonoids are a family of plant derived polyphenolic compounds having considerable scientific and therapeutic importance. Structurally they are the benzo-γ-pyrone derivatives containing phenolic and pyrane rings. Flavonoid radioprotection is an intense area of research thanks to features like natural origin, effectiveness at non-toxic dose levels and lack of side effects. But till date no report is available on the effect of γ-radiation mediated enhancement in radioprotection activity of flavonoids. In view of this the present study was carried out to determine the γ-radiation induced structural changes in selected flavonoids i.e. apigenin, naringenin and genistein and also to explore the possibility of enhancement in their antioxidant and radioprotective activities

Chemical Analysis of the Resinous Exudate Isolated from Heliotropium taltalense and Evaluation of the Antioxidant Activity of the Phenolics Components and the Resin in Homogeneous and Heterogeneous Systems

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René Torres

2009-06-01

Full Text Available H. taltalense (Phil. Johnst. (Heliotropiaceae is an endemic species of the northern coast of Chile that produces a resinous exudate that covers its foliar surface and stems. Its chemical composition was analyzed for the first time, and two aromatic geranyl derivatives: filifolinol and filifolinyl senecionate and three flavonoids – naringenin, 3-O-methylgalangin and 7-O-methyleriodictiol – were isolated. The antioxidant activity of the flavonoids and the resinous exudates was carried out by measuring the 1,1-diphenyl-2-picrylhydrazyl (DPPH bleaching effect in ethanolic solution and in sodium dodecyl sulfate (SDS micelles. The influence of the reaction medium was analyzed. The initial velocity reactions for the pure compounds and for the extract were higher in SDS media than in ethanolic solution. The velocity of reaction observed was interpreted in terms of the reaction medium environment in the micelle.

Chemical analysis of the resinous exudate isolated from Heliotropium taltalense and evaluation of the antioxidant activity of the phenolics components and the resin in homogeneous and heterogeneous systems.

Science.gov (United States)

Modak, Brenda; Rojas, Macarena; Torres, René

2009-06-02

H. taltalense (Phil.) Johnst. (Heliotropiaceae) is an endemic species of the northern coast of Chile that produces a resinous exudate that covers its foliar surface and stems. Its chemical composition was analyzed for the first time, and two aromatic geranyl derivatives: filifolinol and filifolinyl senecionate and three flavonoids - naringenin, 3-O-methylgalangin and 7-O-methyleriodictiol - were isolated. The antioxidant activity of the flavonoids and the resinous exudates was carried out by measuring the 1,1-diphenyl-2-picrylhydrazyl (DPPH) bleaching effect in ethanolic solution and in sodium dodecyl sulfate (SDS) micelles. The influence of the reaction medium was analyzed. The initial velocity reactions for the pure compounds and for the extract were higher in SDS media than in ethanolic solution. The velocity of reaction observed was interpreted in terms of the reaction medium environment in the micelle.

Bioavailability of orange juice (poly)phenols: the impact of short-term cessation of training by male endurance athletes.

Science.gov (United States)

Pereira-Caro, Gema; Polyviou, Thelma; Ludwig, Iziar A; Nastase, Ana-Maria; Moreno-Rojas, José Manuel; Garcia, Ada L; Malkova, Dalia; Crozier, Alan

2017-09-01

Background: Physical exercise has been reported to increase the bioavailability of citrus flavanones. Objective: We investigated the bioavailability of orange juice (OJ) (poly)phenols in endurance-trained males before and after cessation of training for 7 d. Design: Ten fit, endurance-trained males, with a mean ± SD maximal oxygen consumption of 58.2 ± 5.3 mL · kg -1 · min -1 , followed a low (poly)phenol diet for 2 d before drinking 500 mL of OJ containing 398 μmol of (poly)phenols, of which 330 μmol was flavanones. After the volunteers stopped training for 7 d the feeding study was repeated. Urine samples were collected 12 h pre- and 24 h post-OJ consumption. Bioavailability was assessed by the quantitative analysis of urinary flavanone metabolites and (poly)phenol catabolites with the use of high-pressure liquid chromatography-high resolution mass spectrometry. Results: During training, 0-24-h urinary excretion of flavanone metabolites, mainly hesperetin-3'- O -glucuronide, hesperetin-3'-sulfate, naringenin-4'- O -glucuronide, naringenin-7- O -glucuronide, was equivalent to 4.2% of OJ flavanone intake. This increased significantly to 5.2% when OJ was consumed after the volunteers stopped training for 7 d. Overall, this trend, although not significant, was also observed with OJ-derived colonic catabolites, which, after supplementation in the trained state, were excreted in amounts equivalent to 51% of intake compared with 59% after cessation of training. However, urinary excretion of 3 colonic catabolites of bacterial origin, most notably, 3-(3'-hydroxy-4'-methoxyphenyl)hydracrylic acid, did increase significantly when OJ was consumed postcessation compared with precessation of training. Data were also obtained on interindividual variations in flavanone bioavailability. Conclusions: A 7-d cessation of endurance training enhanced, rather than reduced, the bioavailability of OJ flavanones. The biological significance of these differences and whether they

Detection of weak estrogenic flavonoids using a recombinant yeast strain and a modified MCF7 cell proliferation assay

DEFF Research Database (Denmark)

Breinholt, Vibeke; Larsen, John Christian

1998-01-01

A newly developed recombinant yeast strain, in which the human estrogen receptor has been stably integrated into the genome of the yeast, was used to gain information on the estrogenic activity of a large series of dietary flavonoids. Among 23 flavonoids investigated, 8 were found to markedly...... values ranging from 84 to 102 mu M, whereas the remaining flavonoids were devoid of activity. The most potent flavonoid estrogens tested were naringenin, apigenin, kaempferol, phloretin, and the four isoflavonoids equol, genistein, daidzein, and biochanin A. With the exception of biochanin A, the main...... feature required to confer estrogenicity was the presence of a single hydroxyl group in the 4'-position of the B-ring of the flavan nucleus, corresponding to the 4-position on phloretin. The estrogenic potency of the flavonoids was found to be 4 000-4 000 000 times lower than that observed for 17 beta...

The tomato sauce making process affects the bioaccessibility and bioavailability of tomato phenolics: a pharmacokinetic study.

Science.gov (United States)

Martínez-Huélamo, Miriam; Tulipani, Sara; Estruch, Ramón; Escribano, Elvira; Illán, Montserrat; Corella, Dolores; Lamuela-Raventós, Rosa M

2015-04-15

Tomato sauce is the most commonly consumed processed tomato product worldwide, but very little is known about how the manufacturing process may affect the phenolic composition and bioavailability after consumption. In a prospective randomised, cross-over intervention study, we analysed the plasma and urinary levels of tomato phenolic compounds and their metabolites after acute consumption of raw tomatoes and tomato sauce, enriched or not with refined olive oil during production. Respectively, eleven and four phenolic metabolites were found in urine and plasma samples. The plasma concentration and urinary excretion of naringenin glucuronide were both significantly higher after the consumption of tomato sauce than raw tomatoes. The results suggest that the mechanical and thermal treatments during tomato sauce manufacture may help to deliver these potentially bioactive phenolics from the food matrix more effectively than the addition of an oil component, thus increasing their bioavailability. Copyright © 2014 Elsevier Ltd. All rights reserved.

Chemical guide parameters for Spanish lemon (Citrus limon (L.) Burm.) juices.

Science.gov (United States)

Lorente, José; Vegara, Salud; Martí, Nuria; Ibarz, Albert; Coll, Luís; Hernández, Julio; Valero, Manuel; Saura, Domingo

2014-11-01

To contribute for setting reference guideline for commercial juice extracted from the Spanish lemon varieties, chemical composition of 92 direct and 92 reconstituted samples were investigated. In direct lemon juice, titratable acidity was 52.4 g/L, being the citric acid the main component. Glucose, fructose and sucrose concentrations were 7.9, 7.3 and 4.5 g/L, respectively. Predominant mineral was potassium (1264.2mg/L), followed by phosphorous (306 mg/L), calcium (112 mg/L) and magnesium (92.6 mg/L). Hesperidin ranged from 257 to 484.8 mg/L, while water soluble pectins varied between 164.8 and 550 mg/L. Similar values were obtained in reconstituted lemon juice. There are different parameters that did not reach or exceeded the limits proposed by the European Association of the Industry of Juices and Nectars. These levels should be taken into account to modify the present reference guideline and that Spanish lemon juices are not discarded for to have lower or bigger values. Copyright © 2014 Elsevier Ltd. All rights reserved.

Chemical characterization of Citrus sinensis grafted on C. limonia and the effect of some isolated compounds on the growth of Xylella fastidiosa.

Science.gov (United States)

Ribeiro, Alan Bezerra; Abdelnur, Patrícia Verardi; Garcia, Cleverson Fernando; Belini, Adriana; Severino, Vanessa G Pasqualotto; da Silva, M Fátima das G F; Fernandes, João B; Vieira, Paulo C; de Carvalho, Sérgio A; de Souza, Alessandra A; Machado, Marcos A

2008-09-10

Citrus sinensis grafted on C. limonia produces a considerable number of compounds that are not common in both plants developed from germination of seeds. The chemical profile of scion and rootstock differ notably for absence in the form of flavonoids and coumarins containing C5 prenyl groups attached to the carbon atoms of aromatic and heterocyclic systems or to oxygen. Only linear pyranocoumarins xanthyletin and xanthoxyletin were found in scion. This observation indicates that the prenylated compounds once biosynthesized in the roots could have been translocated to other organs. Xylella fastidiosa colonizes the xylem of plants causing diseases on several economically important crops such as citrus variegated chlorosis (CVC). A number of flavonoids, coumarins, alkaloids, dihydrocinnamic acid derivative, anacardic acid, triterpenes, and limonoids were tested for in vitro activity on the growth of Xylella fastidiosa. Azadirachtin A was the most active. Hesperidin, which occurs in great amounts in cells of the mesophyll of the affected leaves with CVC, showed a moderate activity suggesting that it can act as a good barrier for small-size colonies from X. fastidiosa.

Gallic acid as a protective antioxidant against anthocyanin degradation and color loss in vitamin-C fortified cranberry juice.

Science.gov (United States)

Roidoung, Sunisa; Dolan, Kirk D; Siddiq, Muhammad

2016-11-01

The objective of this study was to evaluate different antioxidants for anthocyanin (ACY) retention in vitamin C fortified cranberry juice and assess its quality. Cranberry juice was fortified with 40-80mg/100mL vitamin C and added hesperidin, catechin, and gallic acid at different concentrations. Juice was pasteurized at 85°C for 1min and stored at 23°C for 16days. ACYs, vitamin C, color intensity, and browning index (BI) were evaluated at 2-day intervals. Gallic acid was found to be the most effective antioxidant against ACYs degradation and significantly (p<0.05) increased red color intensity by 37% and ACY concentration by 41%, compared to the control. After 16-day storage, the BI of gallic acid-added juice was significantly lower (0.80 vs 1.00) than the control juice. The outcome of this research provided a potential solution of using gallic acid to preserve a health-beneficial component (ACYs), and endogenous red color in cranberry juice. Copyright © 2016 Elsevier Ltd. All rights reserved.

Phenolic compounds and carotenoids in pumpkin fruit and related traditional products

Directory of Open Access Journals (Sweden)

Zdunić Gordana M.

2016-01-01

Full Text Available Pumpkin fruit is used in a diet since ancient times especially in rural communities. The major contributory factors of nutritional and medicinal value of pumpkins are carotenoids, polysaccharides, vitamins, minerals, and phenolic compounds. Due to a very large fruit that it is not easy to consume a whole as well as short shelf-life of fresh-cut pumpkin, different ways of conserving and processing are performed. In our study, total carotenoids, total phenolics and individual phenolics in fresh pumpkin and pumpkin traditional products such as sweet in wine, jam and juice, which are typical for northern parts of Serbia, were studied. Total carotenoids ranged from 27.6 μg/g of pumpkin sweet in wine to 86.3 μg/g of fresh fruit, while the amount of total phenolics varied between 93.0 μg GAE/g of pumpkin juice and 905.9 μg GAE/g of fresh fruit. Eight phenolic compounds were identified in the investigated samples and among them phenolic acids dominated. Among flavonoids, flavanon glycoside hesperidin was detected. [Projekat Ministarstva nauke Republike Srbije, br. 46013

Phenolic profile and in vitro antioxidant capacity of insoluble dietary fiber powders from citrus (Citrus junos Sieb. ex Tanaka) pomace as affected by ultrafine grinding.

Science.gov (United States)

Tao, Bingbing; Ye, Fayin; Li, Hang; Hu, Qiang; Xue, Shan; Zhao, Guohua

2014-07-23

The effects of mechanical and jet grindings on the proximate composition, phenolics, and antioxidant capacity of insoluble antioxidant dietary fiber powder from citrus pomace (IADFP-CP) were investigated in comparison with ordinary grinding. IADFP-CP from jet grinding showed higher levels of crude fat, total sugar, and free phenolics and lower levels of crude protein and bound phenolics than that from ordinary grinding. Totally, 14 phenolics (9 free, 1 bound, and 4 free/bound) in IADFP-CP were identified by RP-HPLC-DAD/ESI-Q-TOF-MS/MS. Hesperidin accounted for >57% of total phenolics in IADFP-CP. Among IADFP-CPs, the jet-ground presented the highest free phenolics but the lowest bound phenolics. The IADFP-CP from jet grinding presented the highest antioxidant capacity of free phenolics (by DPPH and FRAP assays), followed by the ones from mechanical and then ordinary grinding. The present study suggests that jet grinding could improve the extraction of phenolic compounds from IADFP-CP and increase the antioxidant capacities of free phenolics and the resultant powder.

Protective effects of sweet orange (Citrus sinensis) peel and their bioactive compounds on oxidative stress.

Science.gov (United States)

Chen, Zong-Tsi; Chu, Heuy-Ling; Chyau, Charng-Cherng; Chu, Chin-Chen; Duh, Pin-Der

2012-12-15

Protective effects of sweet orange (Citrus sinensis) peel and their bioactive compounds on oxidative stress were investigated. According to HPLC-DAD and HPLC-MS/MS analysis, hesperidin (HD), hesperetin (HT), nobiletin (NT), and tangeretin (TT) were present in water extracts of sweet orange peel (WESP). The cytotoxic effect in 0.2mM t-BHP-induced HepG2 cells was inhibited by WESP and their bioactive compounds. The protective effect of WESP and their bioactive compounds in 0.2mM t-BHP-induced HepG2 cells may be associated with positive regulation of GSH levels and antioxidant enzymes, decrease in ROS formation and TBARS generation, increase in the mitochondria membrane potential and Bcl-2/Bax ratio, as well as decrease in caspase-3 activation. Overall, WESP displayed a significant cytoprotective effect against oxidative stress, which may be most likely because of the phenolics-related bioactive compounds in WESP, leading to maintenance of the normal redox status of cells. Copyright © 2012 Elsevier Ltd. All rights reserved.

Qualitative analysis of MDR-reversing Anastasia Black (Russian black sweet pepper, Capsicum annuum, Solanaceae) extracts and fractions by HPLC and LC-MS-MS methods.

Science.gov (United States)

Schelz, Zsuzsanna; Molnár, Joseph; Fogliano, Vincenzo; Ferracane, Rosalia; Pernice, Rita; Shirataki, Yoshiaki; Motohashi, Noboru

2006-01-01

In earlier experiments, the MDR (multidrug resistance)-reversal activities of Anastasia Black (Russian black sweet pepper) extracts had been analysed. Recently, the most effective MDR reversing extracts and fractions have been separated by HPLC (high-performance liquid chromatography, for carotenoids) and LC-MS-MS (HPLC combined with mass spectrometry, for phenolic compounds) methods. As a result of the analytical studies, the following flavonoids had been identified: feruloyl glucopyranoside, quercetin rhamnopyranoside glucopyranoside, luteolin glucopyranoside arabinopyranoside, apigenin glucopyranoside arabinopyranoside, quercetin rhamnopyranoside, luteolin arabinopyranoside diglucopy-ranoside, hesperidine and luteolin glucuronide. According to the literature, the aglycones of these phenolic compounds exhibit MDR-reversal activity in vitro, and the connection between the phenolic content of Anastasia Black and MDR-reversal action was therefore studied by different analytical methods. The results of this study revealed that the identified flavonoids of Anastasia Black may be only partially responsible for the modulation of the MDR of mouse lymphoma cells. Other lipophilic compounds, most probably carotenoids, present in Russian black sweet pepper may act as inhibitors of MDR reversal.

Some Analytical Characteristics of Moringa Oleifera Leaves and Seeds Affected by Gamma Irradiation

International Nuclear Information System (INIS)

Aly, A.A.; Maraei, R.A.; Ali, H.G.M.

2014-01-01

Moringa oleifera is an important multipurpose tropical tree under-recognized for its nutritional and medicinal properties. Antioxidants play an important role in inhibiting and scavenging free radicals, thus providing protection to human against infections and degenerative diseases. Leaves and seeds of M. oleifera were subjected to different gamma rays dose levels (0, 5, 10 and 15 kGy) and the content of phenolics, flavonoids, antioxidants activity and the profile of phenolics and flavonoids by HPLC were evaluated. The obtained data indicated that the phenolics and flavonoids content increased gradually by increasing irradiation doses in the seeds and leaves extract. Scavenging activity was increased gradually by increasing irradiation dose levels. Regarding to HPLC analysis of phenolic and flavonoid compounds it was shown that irradiation stimulated the biosynthesis of some phenolic compounds such as, chlorogenic, caffeic, salicycic, ellagic and p-OH-benzoic, as well as rosmarinic, naringin and hyper oside for flavonoids. This study showed that gamma irradiation is an effective tool for enhancing the phenolic compounds and antioxidant activity of M. oleifera.

Assessment by survival analysis of the radioprotective properties of propolis and its polyphenolic compounds

International Nuclear Information System (INIS)

Orsolic, N.; Benkovic, V.; Horvat-Knezevic, A.; Basic, I.; Kopjar, N.; Kosalec, I.; Bakmaz, M.; Mihaljevic, Z.; Bendelja, K.

2007-01-01

The radioprotective effects of propolis and polyphenolic compounds from propolis on the radiation-induced mortality of mice exposed to 9 Gy of γ-irradiation were studied. Intraperitoneal (i.p.) treatment of mice at doses of 100 mgkg -1 body weight of propolis (water or ethanolic extract; water-soluble derivative of propolis (WSDP) or ethanolic extract of propolis (EEP)) or its polyphenolic compounds (quercetin, naringin caffeic acid, chrysin) consecutively for 3 d before irradiation, delayed the onset of mortality and reduced the symptoms of radiation sickness. All test compounds provided protection against hematopoietic death (death within 30 d after irradiation). The greatest protection was achieved with quercetin; the number of survivors at the termination of the experiment was 63%. According to statistical analyses by the Kaplan-Meier method and the log-rank test, a significant difference between test components and control was found (p<0.001). Treatment with test components after lethal irradiation was ineffective. These results suggest that propolis and its polyphenolic compounds given to mice before irradiation protect mice from the lethal effects of whole-body irradiation. (author)

Urinary excretion of flavonoids reflects even small changes in the dietary intake of fruits and vegetables

DEFF Research Database (Denmark)

Brevik, A.; Rasmussen, Salka Elbøl; Drevon, C.A.

2004-01-01

excretion of flavonoids could be used to identify subjects who are meeting Norwegian recommendations for fruit and vegetable intake (5 servings per day) from individuals who are consuming the national average amount of fruits and vegetables (2 servings per day). Design: Twenty-four-hour urine samples were...... collected in a strict crossover controlled feeding study. Forty healthy subjects (19-34 years) were included in the study. After a 1-week run-in period, one group was given a controlled diet that included 2 servings (300 g) of fruits and vegetables daily for 14 days, while the other group was given a diet...... containing 5 servings (750 g) per day. Following a 2-week washout and a 1 week run-in period, the regimens were switched between the groups. Results: An increased intake of mixed fruits and vegetables from 2 to 5 servings per day significantly enhanced urinary excretion of eriodictyol, naringenin, hesperetin...

Suitability of antioxidant capacity, flavonoids and phenolic acids for floral authentication of honey. Impact of industrial thermal treatment.

Science.gov (United States)

Escriche, Isabel; Kadar, Melinda; Juan-Borrás, Marisol; Domenech, Eva

2014-01-01

Total antioxidant activity, physicochemical parameters, and the profile of flavonoids and phenolic acid compounds were evaluated for: their ability to distinguish between the botanical origins of four types of Spanish honey, the impact of industrial thermal treatment, and the effect of the year of collection. Citrus honey had the lowest levels of all the analysed variables, then rosemary and polyfloral, and honeydew the highest ones. Botanical origin affects the profile of flavonoids and phenolic compounds sufficiently to permit discrimination thanks to the predominance of particular compounds such as: hesperetin (in citrus honey); kaempferol, chrysin, pinocembrin, caffeic acid and naringenin (in rosemary honey) and myricetin, quercetin, galangin and particularly p-coumaric acid (in honeydew honey). The impact of industrial thermal treatments is lower than the expected variability as a consequence of the year of collection, though neither factor has enough influence to alter these constituent compounds to the point of affecting the discrimination of honey by botanical origin. Copyright © 2013 Elsevier Ltd. All rights reserved.

Antioxidant Flavonoids from Nepeta floccosa Benth.

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Liaqat Ali

2015-06-01

Full Text Available Antioxidants are the substances which significantly delay or prevent the development of age-related degenerative and chronic diseases caused by oxidative damage. Due to this, there is a considerable interest in the identification of lead molecules, which can inhibit the oxidation process or slow it down considerably. Based on the spectrofluorimetric analysis of superoxide and diphenylpicrylhydrazyl radical scavenging ability, the bio-assay guided isolation of methanolic extract of Nepeta floccosa Benth. was carried out. As a result of this study, one new flavanonol named nepetavanol (1 and four known flavonoids; dihydrokaempferol (2, naringenin (3, caulesnarinside (4, and poncirin (5 have been isolated. The structure of the new flavanonol was assigned on the basis of 1H- and 13C-NMR spectra including two-dimensional NMR techniques such as COSY, HMQC, and HMBC experiments and FABMS, EIMS, HR-MS data. Compound 1 , 2, and 3 showed significant activity whereas compounds 4 and 5 showed moderate activity against antioxidant assays.

Identification of nonvolatile compounds in clove (Syzygium aromaticum) from Manado

Science.gov (United States)

Fathoni, A.; Saepudin, E.; Cahyana, A. H.; Rahayu, D. U. C.; Haib, J.

2017-07-01

Syzygium aromaticum (clove) are native to Indonesia and have been widely used in food industry due to their flavor. Nonvolatile compounds contribute to flavor, mainly in their taste. Currently, there is very little information available about nonvolatile compounds in clove. Identification of nonvolatile compounds is important to improve clove's value. Compound extraction was conducted by maceration in ethanol. Fractionations of the extract were performed by using gravity column chromatography on silica gel and Sephadex LH-20 as stationary phase. Nonvolatile compounds were identified by Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS). LC-MS/MS was operated in negative mode with 0.1 % formic acid in water and acetonitrile as mobile phase. Nonvolatile compounds were identified by fragment analysis and compared to references. Several compounds had been identified and characterized asquinic acid, monogalloylglucose, gallic acid, digalloylglucose, isobiflorin, biflorin, ellagic acid, hydroxygallic acid, luteolin, quercetin, naringenin, kaempferol, isorhamnetin, dimethoxyluteolin, and rhamnetin. These compounds had two main flavor perceptions, i.e. astringent, and bitter.

Metal ion-improved complexation countercurrent chromatography for enantioseparation of dihydroflavone enantiomers.

Science.gov (United States)

Han, Chao; Wang, Wenli; Xue, Guimin; Xu, Dingqiao; Zhu, Tianyu; Wang, Shanshan; Cai, Pei; Luo, Jianguang; Kong, Lingyi

2018-01-12

Cu(II) ion was selected as an additive to improve the enantioseparation efficiency of three dihydroflavone enantiomers in high-speed counter-current chromatography (HSCCC), using hydroxypropyl-β-cyclodextrin (HP-β-CyD) as the chiral selector. The influences of important parameters, including the metal ion, the concentrations of HP-β-CyD and the Cu(II) ion, and the sample size were investigated. Under optimal conditions, three dihydroflavone enantiomers, including (±)-hesperetin, (±)-naringenin, and (±)-farrerol, were successfully enantioseparated. The chiral recognition mechanism was investigated. The enantioseparation was attributed to the different thermodynamic stabilities of the binary complexes of HP-β-CyD and (±)-hesperetin, and Cu(II) ion could enhance this difference by forming ternary complexes with the binary complexes. This Cu(II) ion-improved complexation HSCCC system exhibited improved performance for chiral separation, and therefore it has great application potential in the preparative enantioseparation of other compounds with similar skeletons. Copyright © 2017 Elsevier B.V. All rights reserved.

Identification and characterisation of phenolic compounds extracted from Moroccan olive mill wastewater

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Inass Leouifoudi

2014-06-01

Full Text Available Olive mill wastewater, hereafter noted as OMWW was tested for its composition in phenolic compounds according to geographical areas of olive tree, i.e. the plain and the mountainous areas of Tadla-Azilal region (central Morocco. Biophenols extraction with ethyl acetate was efficient and the phenolic extract from the mountainous areas had the highest concentration of total phenols' content. Fourier-Transform-Middle Infrared (FT-MIR spectroscopy of the extracts revealed vibration bands corresponding to acid, alcohol and ketone functions. Additionally, HPLC-ESI-MS analyses showed that phenolic alcohols, phenolic acids, flavonoids, secoiridoids and derivatives and lignans represent the most abundant phenolic compounds. Nüzhenide, naringenin and long chain polymeric substances were also detected. Mountainous areas also presented the most effective DPPH scavenging potential compared to plain areas; IC50 values were 11.7 ± 5.6 µg/ml and 30.7 ± 4.4 µg/ml, respectively. OMWW was confirmed as a rich source of natural phenolic antioxidant agents.

Magnetic purification of curcumin from Curcuma longa rhizome by novel naked maghemite nanoparticles.

Science.gov (United States)

Magro, Massimiliano; Campos, Rene; Baratella, Davide; Ferreira, Maria Izabela; Bonaiuto, Emanuela; Corraducci, Vittorino; Uliana, Maíra Rodrigues; Lima, Giuseppina Pace Pereira; Santagata, Silvia; Sambo, Paolo; Vianello, Fabio

2015-01-28

Naked maghemite nanoparticles, namely, surface active maghemite nanoparticles (SAMNs), characterized by a diameter of about 10 nm, possessing peculiar colloidal stability, surface chemistry, and superparamagnetism, present fundamental requisites for the development of effective magnetic purification processes for biomolecules in complex matrices. Polyphenolic molecules presenting functionalities with different proclivities toward iron chelation were studied as probes for testing SAMN suitability for magnetic purification. Thus, the binding efficiency and reversibility on SAMNs of phenolic compounds of interest in the pharmaceutical and food industries, namely, catechin, tyrosine, hydroxytyrosine, ferulic acid, coumaric acid, rosmarinic acid, naringenin, curcumin, and cyanidin-3-glucoside, were evaluated. Curcumin emerged as an elective compound, suitable for magnetic purification by SAMNs from complex matrices. A combination of curcumin, demethoxycurcumin, and bis-demethoxycurcumin was recovered by a single magnetic purification step from extracts of Curcuma longa rhizomes, with a purity >98% and a purification yield of 45%, curcumin being >80% of the total purified curcuminoids.

Almond (Prunus dulcis (Mill.) D.A. Webb) polyphenols: from chemical characterization to targeted analysis of phenolic metabolites in humans.

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Bartolomé, Begoña; Monagas, María; Garrido, Ignacio; Gómez-Cordovés, Carmen; Martín-Alvarez, Pedro J; Lebrón-Aguilar, Rosa; Urpí-Sardà, Mireia; Llorach, Rafael; Andrés-Lacueva, Cristina

2010-09-01

In this paper, a survey of our studies on almond polyphenols including their chemical characterization and further bioavailability in humans is reported. Combination of analytical techniques (LC-DAD/fluorescence, LC/ESI-MS and MALDI-TOF-MS) allowed us, for the first time, the identification of A- and B-type procyanidin, propelargonidin and prodelphinidin polymers in almond skins. Glucuronide, O-methyl glucuronide, sulfate and O-methyl sulfate derivatives of (epi)catechin, as well as the glucuronide conjugates of naringenin and isorhamnetin, and sulfate conjugates of isorhamnetin, together with conjugates of hydroxyphenylvalerolactones were detected in plasma and urine samples after the intake of almond skin polyphenols. In addition, numerous microbial-derived metabolites, including hydroxyphenylpropionic, hydroxyphenylacetic, hydroxycinnamic, hydroxybenzoic and hydroxyhippuric acids were also identified. Depending of the type of metabolite, maximum urinary excretion was attained at different time in comparison to the control group in the course of the 24-h period of urine excretion, allowing us to establish the onset of microbial metabolism. 2010 Elsevier Inc. All rights reserved.

Phytochemical screening, anticancer and antioxidant activities of Origanum vulgare L. ssp. viride (Boiss.) Hayek, a plant of traditional usage.

Science.gov (United States)

Koldaş, Serkan; Demirtas, Ibrahim; Ozen, Tevfik; Demirci, Mehmet Ali; Behçet, Lütfi

2015-03-15

A detailed phytochemical analysis of Origanum vulgare L. ssp. viride (Boiss.) Hayek was carried out and the antioxidant activities of five different crude extracts were determined. The antiproliferative activities of the extracts were determined using the xCELLigence system (Real Time Cell Analyzer). Differences between the essential oil and volatile organic compound profiles of the plant were shown. The main component of the essential oil was caryophyllene oxide, while the main volatile organic compounds were sabinene and eucalyptol as determined by HS-GC/MS. Phenolic contents of the extracts were determined qualitatively and quantitatively by HPLC/TOF-MS. Ten phenolic compounds were found in the extracts from O. vulgare and Origanum acutidens: rosmarinic acid (in highest abundance), chicoric acid, caffeic acid, p-coumaric acid, gallic acid, quercetin, apigenin-7-glucoside, kaempferol, naringenin and 4-hydroxybenzaldehyde. This study provides first results on the antiproliferative and antioxidant properties and detailed phytochemical screening of O. vulgare ssp. viride (Boiss.) Hayek. © 2014 Society of Chemical Industry.

Comparative mutagenesis of plant flavonoids in microbial systems

Energy Technology Data Exchange (ETDEWEB)

Hardigree, A.A.; Epler, J.L.

1978-01-01

The plant flavonoids quercetin (3,5,7,3',4'-pentahydroxyflavone), morin (3,5,7,2'4'-pentahydroxyflavone), kaempferol (3,5,7,4'tetrahydroxyflavone), chrysin (5,7-dihydroxyflavone), fisetin (3,7,3',4'-tetrahydroxyflavone), myricetin (3,5,7,3',4',5'-hexahydroxyflavone), myricitrin (myricetin-3-rhamnoside), hesperetin (3',5,7-trihydroxy-4'-methoxyflavanone), quercitrin (quercetin-3-L-rhamnoside), rutin (quercetin-3-rhamnosylglucoside or quercetin-3-rutinoside), and hesperidin (hesperetin-7-rutinoside) have been assayed for mutagenicity in the Salmonella/microsomal activation system. Quercetin, morin, kaempferol, fisetin, myricetin, quercitrin and rutin were mutagenic in the histidine reversion system with the frameshift strain TA98. The flavonols quercetin and myricetin are mutagenic without metabolic activation, although more effective when a rat liver microsomal preparation (S-9) is included; all others require metabolic activation. Flavonoids are common constituents of higher plants, with extensive medical uses. In addition to pure compounds, we have examined crude extracts of tobacco (snuff) and extracts from commonly available nutritional supplements containing rutin. Mutagenic activity can be detected and is correlated with the flavonoid content.

Hesperetin Modifies the Composition of Fecal Microbiota and Increases Cecal Levels of Short-Chain Fatty Acids in Rats.

Science.gov (United States)

Unno, Tomonori; Hisada, Takayoshi; Takahashi, Shunsuke

2015-09-16

There has been particular interest in the prebiotic-like effects of commonly consumed polyphenols. This study aimed to evaluate the effects of hesperidin (HD) and its aglycone hesperetin (HT), major flavonoids in citrus fruits, on the structure and activity of gut microbiota in rats. Rats ingested an assigned diet (a control diet, a 0.5% HT diet, or a 1.0% HD diet) for 3 weeks. Terminal restriction fragment length polymorphism analysis revealed that the proportion of Clostridium subcluster XIVa in the feces collected at the third week of feeding was significantly reduced by the HT diet: 19.8 ± 4.3% for the control diet versus 5.3 ± 1.5% for the HT diet (P acids (SCFA), the sum of acetic, propionic, and butyric acids, between the control diet (212 ± 71 μmol) and the HT diet (310 ± 51 μmol) (P HD diet exhibited no effects (245 ± 51 μmol). Interestingly, dietary HT resulted in a significant increase in the excretion of starch in the feces. HT, but not HD, might reduce starch digestion, and parts of undigested starch were utilized to produce SCFA by microbial fermentation in the large intestine.

Some Biological Compounds, Radical Scavenging Capacities and Antimicrobial Activities in the seeds of Nepeta italica L. and Sideritis montana L. subsp. montana from Turkey

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Erecevit, Pınar

2011-03-01

Full Text Available This study determined some biological compounds (fatty acid compositions, lipid-soluble vitamins, sterols, flavonoids, radical scavenging capacities and antimicrobial activities in the seeds of Nepeta italica L. and Sideritis montana L. subsp. montana. It was found that palmitic acid (C16:0; 8.54±0.13- 3.05±0.04%, oleic acid (C18:1 n9, 22.41±0.8-18.83±0.1% and α-linolenic acid (C18:3 n3;39.56±0.67-77.04±2.07% were the dominant fatty acids in both Nepeta italica L. and Sideritis montana L. subsp. montana. It was concluded that both Nepeta italica L. and Sideritis montana L. subsp. montana contained stigmasterol (630.07±1.81µg/g, 80.74±0.71µg/g, respectively and ergosterol (1.11±0.14µg/g, 161.32±0.63µg/g respectively as well as beta-sitosterol (2.93±0.03 µg/g. The present findings show that Nepeta italica L. contains morin (37.79±1.09μg/g, catechin (124.39±2.23µg/g, naringin (475.96±3.57µg/g and Sideritis montana L. subsp. montana contains morin (188.41±2.53µg/g, catechin (64.14±1.86μg/g, naringenin (38.34±1.78μg/g as major flavonoids. It was also determined that methanol extracts of Nepeta italica L. and Sideritis montana L. subsp. montana were most effective against DPPH radicals. The results of the present study show that the vitamins, flavonoids and fatty acid extracts in the seeds of N. italica L. and S. montana L. subsp. montana prevented the growth of the microorganisms used in the tests at different ratios.Este estudio ha determinado algunos compuestos biológicos (ácidos grasos, vitaminas liposolubles, esteroles y flavonoides, capacidad atrapadora de radicales libres, y actividades antimicrobianas de las semillas de Nepeta italica L. y Sideritis montana L. subsp. montana. Se encontró que el ácido palmítico (C16:0; 8.54±0.13-3.05±0.04%, ácido oleico (C18:1 n9, 22.41±0.8-18.83±0.1% y α-linolénico (C18:3 n 3;39.56±0.67-77.04±2.07% eran mayoritarios en ambas semillas de Nepeta italica L. y Sideritis

Comparative pharmacokinetics of swertiamarin in rats after oral administration of swertiamarin alone, Qing Ye Dan tablets and co-administration of swertiamarin and oleanolic acid.

Science.gov (United States)

Xu, Gui-li; Li, Hong-liang; He, Jian-chang; Feng, En-fu; Shi, Pan-pan; Liu, Yue-qiong; Liu, Chang-xiao

2013-08-26

Qing Ye Dan is a well-known herbal drug that is widely used to treat viral hepatitis in the Yi and Hani minority regions in the Yunnan province of China. An LC-MS/MS method was developed to determine the levels of swertiamarin in rat plasma. Swertiamarin and naringin (internal standard, IS) were extracted from rat plasma using solid-phase extraction (SPE) to purify the samples. The pharmacokinetics of the following different administration methods of swertiamarin in rats were studied: oral administration of swertiamarin alone, a Qing Ye Dan tablet (QYDT) and co-administration of swertiamarin and oleanolic acid, with each method delivering approximately 20mg/kg of swertiamarin. Non-compartmental pharmacokinetic profiles were constructed by using the software DAS (version 2.1.1), and the pharmacokinetic parameters were compared using an unpaired Student's t-test. The results showed that the pharmacokinetic parameters Cmax, AUC0-∞, Vz/F and CLz/F were significantly different (P<0.05) among the three types of swertiamarin administration. The data indicate that oleanolic acid and the other ingredients present in QYDT could affect the pharmacokinetic behaviour of swertiamarin in rats. Copyright © 2013 Elsevier Ireland Ltd. All rights reserved.

Characterization of putative receptors specific for quercetin on bovine aortic smooth-muscle cells

International Nuclear Information System (INIS)

Yu, S.C.; Becker, C.G.

1986-01-01

The authors have reported that tobacco glycoprotein (TGP), rutin-bovine serum albumin conjugates (R-BSA), quercetin, and chlorogenic acid are mitogenic for bovine aortic smooth-muscle cells (SMC). To investigate whether there are binding sites or receptors for these polyphenol-containing molecules on SMC, the authors have synthesized 125 I-labeled rutin-bovine serum albumin ([ 125 I]R-BSA) of high specific activity (20 Ci/mmol). SMC were isolated from a bovine thoracic aorta and maintained in Eagle's minimum essential medium with 10% calf serum in culture. These SMC at early subpassages were suspended (3-5 x 10 7 cells/ml) in phosphate-buffered saline and incubated with [ 125 I]R-BSA (10 pmol) in the presence or absence of 200-fold unlabeled R-BSA, TGP, BSA, rutin, quercetin or related polyphenols, and catecholamines. Binding of [ 125 I]R-BSA to SMC was found to be reproducible and the radioligand was displaced by R-BSA, and also by TGP, rutin, quercetin, and chlorogenic acid, but not by BSA, ellagic acid, naringin, hesperetin, dopamine, epinephrine, or isoproterenol. The binding was saturable, reversible, and pH-dependent. These results demonstrate the presence of specific binding sites for quercetinon arterial SMC

Evaluation of Plant Phenolic Metabolites as a Source of Alzheimer's Drug Leads

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Yara Hassaan

2014-01-01

Full Text Available Epidemiological studies have proven an association between consumption of polyphenols and prevention of Alzheimer’s disease, the most common form of dementia characterized by extracellular deposition of amyloid beta plaques. The aim of this study is pharmacological screening of the aqueous alcohol extract of Markhamia platycalyx leaves, Schotia brachypetala leaves and stalks, and piceatannol compared to aqueous alcohol extract of Camellia sinensis leaves as potential Alzheimer’s disease drugs. LC-HRESI(-ve-MSn was performed to identify phenolics’ profile of Schotia brachypetala stalks aqueous alcohol extract and revealed ten phenolic compounds as first report: daidzein, naringin, procyanidin isomers, procyanidin dimer gallate, quercetin 3-O-rhamnoside, quercetin 3-O-glucuronide, quercetin hexose gallic acid, quercetin hexose protocatechuic acid, and ellagic acid. Alzheimer’s disease was induced by a single intraperitoneal injection of LPS. Adult male Swiss albino mice were divided into groups of 8–10 mice each receiving treatment for six days. In vivo behavioral tests (Y maze and object recognition and in vitro estimation of amyloid beta 42 by ELISA showed significant differences between results of treated and nontreated animals.

Food Polyphenol Apigenin Inhibits the Cytochrome P450 Monoxygenase Branch of the Arachidonic Acid Cascade.

Science.gov (United States)

Steuck, Maryvonne; Hellhake, Stefan; Schebb, Nils Helge

2016-11-30

The product of cytochrome P450 monooxygenase (P450) ω-hydroxylation of arachidonic acid (AA), 20- hydroxyeicosatetraenoic acid (HETE), is a potent vasoconstrictor. Utilizing microsomes as well as individual CYP4 isoforms we demonstrate here that flavonoids can block 20-HETE formation. Apigenin inhibits CYP4F2 with an IC 50 value of 4.6 μM and 20-HETE formation in human liver and kidney microsomes at 2.4-9.8 μM. Interestingly, the structurally similar naringenin shows no relevant effect on the formation of 20-HETE. Based on these in vitro data, it is impossible to evaluate if a relevant blockade of 20-HETE formation can result in humans from intake of polyphenols with the diet. However, the potency of apigenin is comparable to those of P450 inhibitors such as ketoconazole. Moreover, an IC 50 value in the micromolar range is also described for the inhibition of CYP-mediated drug metabolism leading to food-drug interactions. The modulation of the arachidonic acid cascade by food polyphenols therefore warrants further investigation.

New Cytotoxic Bibenzyl and Other Constituents from Bauhinia ungulata L. (Fabaceae).

Science.gov (United States)

de Sousa, Leôncio M; de Carvalho, Jarbas L; da Silva, Horlando C; Lemos, Telma L G; Arriaga, Angela M C; Braz-Filho, Raimundo; Militão, Gardênia C G; Silva, Thiago D S; Ribeiro, Paulo R V; Santiago, Gilvandete M P

2016-12-01

A new bibenzyl, 2'-hydroxy-3,5-dimethoxy-4-methylbibenzyl (1) and four known compounds identified as 2'-hydroxy-3,5-dimethoxybibenzyl (2), liquiritigenin (3), guibourtinidol (4) and fisetinidol (5) were isolated from the roots of Bauhinia ungulata L. Phytochemical investigations of the stems of B. ungulata led to the isolation of the known compounds identified as liquiritigenin (3), guibourtinidol (4), fisetinidol (5), taraxerol (6), betulinic acid (7), taraxerone (8), glutinol (9), a mixture of sitosterol (10) and stigmasterol (11), pacharin (12), naringenin (13) and eriodictyol (14). The structures of these compounds were elucidated on the basis of their spectral data (IR, MS, 1D- and 2D-NMR). The cytotoxicity of the bibenzyl 1 has been evaluated against four human cancer cell lines, showing the IC 50 values of 4.3 and 6.5 μg ml -1 against pro-myelocytic leukemia (HL-60) and cervical adenocarcinoma (HEP-2) cell lines, respectively. This article also registers for the first time the 13 C-NMR data of the known bibenzyl 2. © 2016 Wiley-VHCA AG, Zurich, Switzerland.

The impact of high pressure processing on the phenolic profile, hydrophilic antioxidant and reducing capacity of purée obtained from commercial tomato varieties.

Science.gov (United States)

Jeż, Maja; Wiczkowski, Wiesław; Zielińska, Danuta; Białobrzewski, Ireneusz; Błaszczak, Wioletta

2018-09-30

The effect of high hydrostatic pressure (HHP) (450-550-650 MPa/5-10-15 min) on polyphenols profile of purée obtained from commercial tomato varieties (Maliniak, Cerise, Black Prince and Lima) was investigated. Individual polyphenols, total phenolic index (TPI) were quantified using a mass spectrometer (HPLC-MS/MS). Photochemiluminescence (PCLACW), cyclic voltammetry (CV) and ferric reducing antioxidant power (FRAP) assays were used to determine the antioxidant capacity of the hydrophilic extract. The results demonstrated that at certain processing conditions, HHP may enhance or decrease the nutritional quality of tomato purée. However, the tomato variety was a key factor influencing the polyphenols profile and the antioxidant capacity. A significant positive correlation was found among TPI, FRAP or CV parameters and the concentration of caffeic, ferulic, sinapic and p-coumaric acids, and epicatechin. On the other hand, significant positive correlation was observed among antioxidant capacity (PCLACW), TPC, rutin and naringenin concentration as well as chlorogenic and isochlorogenic acids. Copyright © 2018 Elsevier Ltd. All rights reserved.

Bioavailability, metabolism and potential health protective effects of dietary flavonoids

DEFF Research Database (Denmark)

Bredsdorff, Lea

Dietary flavonoids constitute an important group of potential health protective compounds from fruits, vegetables, and plant-based products such as tea and wine. The beneficial effects of a diet high in flavonoids on the risk of coronary heart disease (CHD) have been shown in several epidemiologi......Dietary flavonoids constitute an important group of potential health protective compounds from fruits, vegetables, and plant-based products such as tea and wine. The beneficial effects of a diet high in flavonoids on the risk of coronary heart disease (CHD) have been shown in several...... of their content. In addition, variation in individual metabolic genotype and microflora may greatly affect the actual flavonoid exposure. The preventive effects of flavonoids on CHD are mainly ascribed to their anti-inflammatory and antioxidant activities. Several mechanisms of anti-inflammatory and antioxidant...... effective absorption of hesperetin and naringenin from the small intestine when consumed as glucosides compared to absorption in the colon VII after microbial degradation of the rhamnoglucosides. In addition it was shown that the conjugate profile was neither affected by the absorption site nor by a 3-fold...

Determination of Polar Compounds in Guava Leaves Infusions and Ultrasound Aqueous Extract by HPLC-ESI-MS

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Elixabet Díaz-de-Cerio

2015-01-01

Full Text Available Literature lacks publications about polar compounds content in infusion or guava leaves tea. Because of that, a comparison between different times of infusion and a conventional ultrasound aqueous extract was carried out. Several polar compounds have been identified by HPLC-ESI-MS and their antioxidant activity was evaluated by FRAP and ABTS assays. Four different classes of phenolic compounds (gallic and ellagic acid derivatives, flavonols, flavanones, and flavan-3-ols and some benzophenones were determined. The quantification results reported that the order, in terms of concentration of the classes of polar compounds in all samples, was flavonols > flavan-3-ols > gallic and ellagic acid derivatives > benzophenones > flavanones. As expected, the aqueous extract obtained by sonication showed the highest content in the compounds studied. Significative differences were noticed about the different times of infusion and five minutes was the optimal time to obtain the highest content in polar compounds using this culinary method. All the identified compounds, except HHDP isomers and naringenin, were positively correlated with antioxidant activity.

An environmentally friendly procedure to obtain flavonoids from Brazilian citrus waste

Energy Technology Data Exchange (ETDEWEB)

Bellete, Barbara S.; Ramin, Luize Z.; Porto, Deyvid; Ribeiro, Alany I.; Forim, Moacir R.; Zuin, Vânia G.; Fernandes, João B.; Silva, Maria Fátima G.F., E-mail: barbarabellete@gmail.com [Departamento de Química, Universidade Federal de São Carlos, SP (Brazil)

2018-05-01

Currently, most food waste is used as animal feed and this process does not take advantage of the available chemical composition. A Brazilian example is the citrus fruit processing wastes (CFPW), which have begun to draw attention due to their biological importance. In order to access the main compounds of this matrix, an efficient and environmentally friendly procedure was tested. From this extract, flavonoids as naringenin, hesperitin, chrysoeriol, sinensetin, 3,5,6,7,3',4'-hexamethoxyflavone, nobiletin, 5-methoxysalvigenin, 3,5,6,7,8,3',4'-heptamethoxyflavone, 3,5,6,7,4'-pentamethoxyflavone and isosakuranetin were identified by high performance liquid chromatography (HPLC-UV), liquid chromatography-mass spectrometry (LC-MS) and liquid chromatography-nuclear magnetic resonance (LC-NMR). This study describes the potential use of citrus waste as a source of biologically active compounds. The extraction method proposed for this work was not expensive and the flavonoids were obtained in large amounts, thus, this extraction method is being developed using pilot plant scale-up techniques and will soon be available to the industry at a low cost. (author)

Formation of flavone di-O-glucosides using a glycosyltransferase from Bacillus cereus.

Science.gov (United States)

Ahn, Byoung Chan; Kim, Bong Gyu; Jeon, Young Min; Lee, Eun Jeong; Lim, Yoongho; Ahn, Joong-Hoon

2009-04-01

Microbial UDP-glycosyltransferases can convert many small lipophilic compounds into glycons using uridinediphosphate- activated sugars. The glycosylation of flavonoids affects solubility, stability, and bioavailability. The gene encoding the UDP-glycosyltransferase from Bacillus cereus, BcGT-3, was cloned by PCR and sequenced. BcGT-3 was expressed in Escherichia coli BL21 (DE3) with a glutathione S-transferase tag and purified using a glutathione Stransferase affinity column. BcGT-3 was tested for activity on several substrates including genistein, kaempferol, luteolin, naringenin, and quercetin. Flavonols were the best substrates for BcGT-3. The enzyme dominantly glycosylated the 3-hydroxyl group, but the 7-hydroxyl group was glycosylated when the 3-hydroxyl group was not available. The kaempferol reaction products were identified as kaempferol-3-O-glucoside and kaempferol- 3,7-O-diglucoside. Kaempferol was the most effective substrate tested. Based on HPLC, LC/MS, and NMR analyses of the reaction products, we conclude that BcGT-3 can be used for the synthesis of kaempferol 3,7-O-diglucose.

Flavan hetero-dimers in the Cymbopogon citratus infusion tannin fraction and their contribution to the antioxidant activity.

Science.gov (United States)

Costa, Gustavo; González-Manzano, Susana; González-Paramás, Ana; Figueiredo, Isabel Vitória; Santos-Buelga, Celestino; Batista, Maria Teresa

2015-03-01

Cymbopogon citratus (lemongrass) leaf infusion, a commonly used ingredient in Asian, African and Latin American cuisines, is also used in traditional medicine for the treatment of several pathological conditions; however, little is known about their bioactive compounds. Recent studies revealed the crucial role of the phenolic compounds namely flavonoids and tannins on the infusion bioactivity. Flavonoids have already been characterized; however the tannin fraction of lemongrass infusion is still uncharted. The aim of the present work is to characterize this fraction, and to evaluate its contribution to the antioxidant potential of this plant. Chemical characterization was achieved by HPLC-DAD-ESI/tandem MS and the antioxidant activity was evaluated using DPPH, ABTS and FRAP assays. Hetero-dimeric flavan structures have been described for the first time in lemongrass consisting of apigeniflavan or luteoliflavan units linked to a flavanone, either naringenin or eriodictyol, which may occur as aglycone or glycosylated forms. The antioxidant capacity of the fraction containing these compounds was significantly higher than the infusion, indicating its potential as a source of natural antioxidants.

Improved thermostable polyvinyl alcohol electrospun nanofibers with entangled naringinase used in a novel mini-packed bed reactor.

Science.gov (United States)

Nunes, Mário A P; Martins, Samuel; Rosa, M Emilia; Gois, Pedro M P; Fernandes, Pedro C B; Ribeiro, Maria H L

2016-08-01

Polyvinyl alcohol (PVA) electrospun nanofibers were produced using an electrospinning technique. Key parameters (e.g. collectors, distance from needle tip to collector, among others) that influence the structure and morphology of fibers were optimized. The naringinase entrapped in PVA nanofibers retained over 100% of its initial activity after 212h of operation, at 25°C. Chemical crosslinking with several boronic acids further increased the hydrolysis temperature (up to 85°C) and yielded nanofibers with thermal stability up to 121°C. A mini packed bed reactor (PBR) developed to establish the feasibility for continuous enzymatic operation, ran for 16days at 45°C. Highest naringenin biosynthesis was attained at a flow rate of 10mLh(-1). Highest volumetric (78molL(-1)h(-1)) and specific (26molh(-1)genzyme(-1)) productivities were attained at 30mLh(-1). The activity of NGase in electrospun nanofibers remained constant for almost 16days of operation at 10mLh(-1). Copyright © 2016 Elsevier Ltd. All rights reserved.

An environmentally friendly procedure to obtain flavonoids from Brazilian citrus waste

International Nuclear Information System (INIS)

Bellete, Barbara S.; Ramin, Luize Z.; Porto, Deyvid; Ribeiro, Alany I.; Forim, Moacir R.; Zuin, Vânia G.; Fernandes, João B.; Silva, Maria Fátima G.F.

2018-01-01

Currently, most food waste is used as animal feed and this process does not take advantage of the available chemical composition. A Brazilian example is the citrus fruit processing wastes (CFPW), which have begun to draw attention due to their biological importance. In order to access the main compounds of this matrix, an efficient and environmentally friendly procedure was tested. From this extract, flavonoids as naringenin, hesperitin, chrysoeriol, sinensetin, 3,5,6,7,3',4'-hexamethoxyflavone, nobiletin, 5-methoxysalvigenin, 3,5,6,7,8,3',4'-heptamethoxyflavone, 3,5,6,7,4'-pentamethoxyflavone and isosakuranetin were identified by high performance liquid chromatography (HPLC-UV), liquid chromatography-mass spectrometry (LC-MS) and liquid chromatography-nuclear magnetic resonance (LC-NMR). This study describes the potential use of citrus waste as a source of biologically active compounds. The extraction method proposed for this work was not expensive and the flavonoids were obtained in large amounts, thus, this extraction method is being developed using pilot plant scale-up techniques and will soon be available to the industry at a low cost. (author)

Antioxidant Activities of Selected Berries and Their Free, Esterified, and Insoluble-Bound Phenolic Acid Contents

Science.gov (United States)

2018-01-01

To explore the potential of berries as natural sources of bioactive compounds, the quantities of free, esterified, and insoluble-bound phenolic acids in a number of berries were determined. In addition, the antioxidant activities of the berries were determined using 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, ferric reducing antioxidant power, and Trolox equivalent antioxidant capacity assays, in addition to determination of their metal ion chelating activities. Furthermore, several phenolic compounds were detected using high-performance liquid chromatography. Of the 6 tested berries, black chokeberry and blackberry exhibited the strongest antioxidant activities, and the various berry samples were found to contain catechin, caffeic acid, p-coumaric acid, epicatechin, vanillic acid, quercitrin, resveratrol, morin, naringenin, and apigenin. Moreover, the antioxidant activities and total phenolic contents of the fractions containing insoluble-bound phenolic acids were higher than those containing the free and esterified phenolic acids. The results imply that the insoluble-bound fractions of these berries are important natural sources of antioxidants for the preparation of functional food ingredients and preventing diseases associated with oxidative stress. PMID:29662846

Comparison of the phenolic composition of fruit juices by single step gradient HPLC analysis of multiple components versus multiple chromatographic runs optimised for individual families.

Science.gov (United States)

Bremner, P D; Blacklock, C J; Paganga, G; Mullen, W; Rice-Evans, C A; Crozier, A

2000-06-01

After minimal sample preparation, two different HPLC methodologies, one based on a single gradient reversed-phase HPLC step, the other on multiple HPLC runs each optimised for specific components, were used to investigate the composition of flavonoids and phenolic acids in apple and tomato juices. The principal components in apple juice were identified as chlorogenic acid, phloridzin, caffeic acid and p-coumaric acid. Tomato juice was found to contain chlorogenic acid, caffeic acid, p-coumaric acid, naringenin and rutin. The quantitative estimates of the levels of these compounds, obtained with the two HPLC procedures, were very similar, demonstrating that either method can be used to analyse accurately the phenolic components of apple and tomato juices. Chlorogenic acid in tomato juice was the only component not fully resolved in the single run study and the multiple run analysis prior to enzyme treatment. The single run system of analysis is recommended for the initial investigation of plant phenolics and the multiple run approach for analyses where chromatographic resolution requires improvement.

Enzymatic Properties and Mutational Studies of Chalcone Synthase from Physcomitrella patens

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Mahiran Basri

2012-08-01

Full Text Available PpCHS is a member of the type III polyketide synthase family and catalyses the synthesis of the flavonoid precursor naringenin chalcone from p-coumaroyl-CoA. Recent research reports the production of pyrone derivatives using either hexanoyl-CoA or butyryl-CoA as starter molecule. The Cys-His-Asn catalytic triad found in other plant chalcone synthase predicted polypeptides is conserved in PpCHS. Site directed mutagenesis involving these amino acids residing in the active-site cavity revealed that the cavity volume of the active-site plays a significant role in the selection of starter molecules as well as product formation. Substitutions of Cys 170 with Arg and Ser amino acids decreased the ability of the PpCHS to utilize hexanoyl-CoA as a starter molecule, which directly effected the production of pyrone derivatives (products. These substitutions are believed to have a restricted number of elongations of the growing polypeptide chain due to the smaller cavity volume of the mutant’s active site.

THE EFFECT OF THE MANUFACTURING PROCESS ON THE CITRUS JUICE ON THE CONCENTRATIONS OF FLAVANONES

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Lílian Maria MOURA

2009-06-01

Full Text Available

Flavonoids are polyphenolic compounds in fruits, vegetables, grains, etc with antioxidant capacity and anti-inflamatory, anticoagulant, antiallergic proprieties that contributes to human health. The effect of the pasteurization and concentration processes on the citric juices can influence the composition of the flavanones. The flavanones composition in the orange juice (a mixture of Pera and Valencia and of the tangor Murcott was determined by HPLC. The flavanones (narirutin and hesperidin were extracted with methanol, heated in 55°C for 15 minutes and separated from the insoluble solids by centrifugation. The separation was done in C18 column (5μm, 250x4.6mm using the isocratic system of acetonitrile mixture: water, acetic acid (21:75:4v/v/v in a flow of 0.6L/min, detention of 280nm and quantification by external pattern. The effect of the pasteurization and concentration on the citric juice did not affect significantly the amount of flavones in the samples of murcott and orange juice (mixture Pera and Valencia.

Preparation and structural studies on organotin(IV) complexes with flavonoids

International Nuclear Information System (INIS)

Nagy, L.; Christy, A.A.; Sletten, E.; Andersen, Q.M.; Edelmann, F.T.

1998-01-01

Fourteen complexes of di-n-butyltin(IV) 2+ cations with flavonoid glycosides (rutin, hesperidin, 2',4',3-trihydroxy-5',4-dimetoxychalkone 4-rutinoside) and flavonoid aglycones (quercetin, morin, hesperitin and sorte flavones) were prepared. The composition of the complexes was determined by standard analytical methods. The results showed that complexes containing diorganotin(IV) 2+ moiety and the ligand in 1:1, 2:1 or 3:1 ratio are formed. The FTIR spectra were consistent with the presence of Sn-O (phenol or carbohydrate) vibration in the compounds. The structure of the complexes was measured by Moessbauer spectroscopy. Comparison of the experimental quadrupole splitting with those calculated on the basis of partial quadrupole splitting concept revealed that the complexes are of four types: with the central tin atoms surrounded by donor atoms in a purely trigonal-bipyramidal, octahedral+trigonal-bipyramidal, trigonal-bipyramidal+tetrahedral and octahedral+tetrahedral arrangement. This procedure also distinguished between the different structural isomers of both trigonal-bipyramidal and octahedral complexes. Conclusions could therefore be drawn on the factors determining which of the isomers are formed in the systems. The Moessbauer parameters obtained for organotin(IV)-flavonoid complexes were compared with those measured for organotin(IV)-carbohydrate complexes. (author)

Nine Different Chemical Species and Action Mechanisms of Pancreatic Lipase Ligands Screened Out from Forsythia suspensa Leaves All at One Time.

Science.gov (United States)

Chen, Tinggui; Li, Yayun; Zhang, Liwei

2017-05-12

It is difficult to screen out as many active components as possible from natural plants all at one time. In this study, subfractions of Forsythia suspensa leaves were firstly prepared; then, their inhibitive abilities on pancreatic lipase were tested; finally, the highest inhibiting subfraction was screened by self-made immobilized pancreatic lipase. Results showed that nine ligands, including eight inhibitors and one promotor, were screened out all at one time. They were three flavonoids (rutin, IC 50 : 149 ± 6.0 μmol/L; hesperidin, 52.4 μmol/L; kaempferol-3- O -rutinoside, isolated from F. suspensa leaves for the first time, IC 50 notably reached 2.9 ± 0.5 μmol/L), two polyphenols (chlorogenic acid, 3150 ± 120 μmol/L; caffeic acid, 1394 ± 52 μmol/L), two lignans (phillyrin, promoter; arctigenin, 2129 ± 10.5 μmol/L), and two phenethyl alcohol (forsythiaside A, 2155 ± 8.5 μmol/L; its isomer). Their action mechanisms included competitive inhibition, competitive promotion, noncompetitive inhibition, and uncompetitive inhibition. In sum, using the appropriate methods, more active ingredients can be simply and quickly screened out all at one time from a complex natural product system. In addition, F. suspensa leaves contain numerous inhibitors of pancreatic lipase.

The potential role of polyphenols in the modulation of skin cell viability by Aspalathus linearis and Cyclopia spp. herbal tea extracts in vitro.

Science.gov (United States)

Magcwebeba, Tandeka Unathi; Riedel, Sylvia; Swanevelder, Sonja; Swart, Pieter; De Beer, Dalene; Joubert, Elizabeth; Andreas Gelderblom, Wentzel Christoffel

2016-11-01

The relationship between polyphenol constituents, antioxidant properties of aqueous and methanol extracts of green tea (Camellia sinensis), the herbal teas, rooibos (Aspalathus linearis) and honeybush (Cyclopia spp.), against skin cell viability was investigated in vitro. The effect of extracts, characterised in terms of polyphenol content and antioxidant properties, on cell viability of premalignant, normal and malignant skin cells was determined. Phenolic composition, particularly high levels of potent antioxidants, of rooibos and green tea methanol extracts was associated with a strong reduction in cell viability specifically targeting premalignant cells. In contrast, the aqueous extracts of Cyclopia spp. were more effective in reducing cell viability. This correlated with a relatively high flavanol/proanthocyanidin content and ABTS radical cation scavenging capacity. The major green tea flavanol (epigallocatechin gallate) and rooibos dihydrochalcone (aspalathin) exhibited differential effects against cell viability, while the major honeybush xanthone (mangiferin) and flavanone (hesperidin) lacked any effect presumably due to a cytoprotective effect. The underlying mechanisms against skin cell viability are likely to involve mitochondrial dysfunction resulting from polyphenol-iron interactions. The polyphenol constituents and antioxidant parameters of herbal tea extracts are useful tools to predict their activity against skin cell survival in vitro and potential chemopreventive effects in vivo. © 2016 Royal Pharmaceutical Society.

Pharmacognostical and phytochemical studies on Ziziphora clinopodioides Lam. – A Kazakh and Uygur ethnomedicinal plant

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Yun Zhu

2017-11-01

Full Text Available Context: Ziziphora clinopodioides Lam. (Lamiaceae is an annual or perennial herb or subshrub widely distributed from the Mediterranean to central Asia and Afghanistan. In Xinjiang, China, the whole herb has been used in traditional Kazakh and Uygur medicines as anti-febrile and detoxicating drug. Aims: To characterize macroscopical, microscopically of the overground part of the Z. clinopodioides, explore and establish the macro-morphology, micro-morphology, quality and physicochemical parameters standards for this plant. Methods: Pharmacognostical and phytochemical investigations were conducted in terms of macroscopic, microscopic and preliminary phytochemical parameters. Results: The vegetable material can be identified by structural features of the flowers, structural characteristics of the stem, specific pale brown hesperidin can be regarded as identification character. This crude drug showed the characteristic physicochemical values like total ash (7%, insoluble ash (1.3%, water soluble ash (3.7%, moisture (7.5%. The ethanolic extract contained flavonoids, organic acids, alkaloids, and glycosides. Conclusions: Various pharmacognostical characters that observed in this study can be an effective supplement to further research of this ethnomedicinal plant. Meanwhile, the results of this paper deal with pharmacognostical studies on the Ziziphora clinopodioides in an attempt to mitigate the adulteration to the crude drug.

Antioxidant activity and phenolic profile of pistachio (Pistacia vera L., variety Bronte) seeds and skins.

Science.gov (United States)

Tomaino, Antonio; Martorana, Maria; Arcoraci, Teresita; Monteleone, Domenico; Giovinazzo, Corrado; Saija, Antonella

2010-09-01

Pistachio (Pistacia vera L.; Anacardiaceae) is native of aride zones of Central and West Asia and distributed throughout the Mediterranean basin. In Italy, a pistachio cultivar of high quality is typical of Bronte (Sicily), an area around the Etna volcano, where the lava land and climate allow the production of a nut with intense green colour and aromatic taste, very appreciated in international markets. Pistachio nuts are a rich source of phenolic compounds, and have recently been ranked among the first 50 food products highest in antioxidant potential. Pistachio nuts are often used after removing the skin, which thus represents a significant by-product of pistachio industrial processing. The present study was carried out to better characterize the phenolic composition and the antioxidant activity of Bronte pistachios, with the particular aim to evaluate the differences between pistachio seeds and skins. The total content of phenolic compounds in pistachios was shown to be significantly higher in skins than in seeds. By HPLC analysis, gallic acid, catechin, eriodictyol-7-O-glucoside, naringenin-7-O-neohesperidoside, quercetin-3-O-rutinoside and eriodictyol were found both in pistachio seeds than in skins; furthermore, genistein-7-O-glucoside, genistein, daidzein and apigenin appeared to be present only in pistachio seeds, while epicatechin, quercetin, naringenin, luteolin, kaempferol, cyanidin-3-O-galactoside and cyanidin-3-O-glucoside are contained only in pistachio skins. The antioxidant activity of pistachio seeds and skins were determined by means of four different assays (DPPH assay, Folin-Ciocalteau colorimetric method and TEAC assay, SOD-mimetic assay). As expected on the basis of the chemical analyses, pistachio skins have shown to possess a better activity with respect to seeds in all tests. The excellent antioxidant activity of pistachio skins can be explained by its higher content of antioxidant phenolic compounds. By HPLC-TLC analysis, gallic acid

Bioavailability enhancers of herbal origin: An overview

Science.gov (United States)

Kesarwani, Kritika; Gupta, Rajiv

2013-01-01

Recently, the use of herbal medicines has been increased all over the world due to their therapeutic effects and fewer adverse effects as compared to the modern medicines. However, many herbal drugs and herbal extracts despite of their impressive in-vitro findings demonstrates less or negligible in-vivo activity due to their poor lipid solubility or improper molecular size, resulting in poor absorption and hence poor bioavailability. Nowadays with the advancement in the technology, novel drug delivery systems open the door towards the development of enhancing bioavailability of herbal drug delivery systems. For last one decade many novel carriers such as liposomes, microspheres, nanoparticles, transferosomes, ethosomes, lipid based systems etc. have been reported for successful modified delivery of various herbal drugs. Many herbal compounds including quercetin, genistein, naringin, sinomenine, piperine, glycyrrhizin and nitrile glycoside have demonstrated capability to enhance the bioavailability. The objective of this review is to summarize various available novel drug delivery technologies which have been developed for delivery of drugs (herbal), and to achieve better therapeutic response. An attempt has also been made to compile a profile on bioavailability enhancers of herbal origin with the mechanism of action (wherever reported) and studies on improvement in drug bioavailability, exhibited particularly by natural compounds. PMID:23620848

Phytochemical Prospection and Modulation of Antibiotic Activity In Vitro by Lippia origanoides H.B.K. in Methicillin Resistant Staphylococcus aureus

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Humberto Medeiros Barreto

2014-01-01

Full Text Available The Lippia origanoides H.B.K. ethanol extract (LOEE and hexane (LOHEX, dichloromethane (LODCM, and ethyl acetate (LOEA fractions were tested for their antimicrobial activity alone or in combination with antibiotics against a methicillin resistant Staphylococcus aureus (MRSA strain. The natural products did not show antimicrobial activity against multidrug resistant strain at the clinically significant concentrations tested. However, a modulatory effect in the antibacterial activity of the neomycin and amikacin was verified when LOEE, LOHEX and LODCM were added to the growth medium at subinhibitory concentrations. A similar modulation was found when the natural products were changed for chlorpromazine, an inhibitor of bacterial efflux pumps, suggesting the involvement of resistance mediated by efflux system in the MRSA tested. The fractions LOHEX and LODCM showed a modulatory activity bigger than their majority compounds (carvacrol, thymol, and naringenin, indicating that this activity is not due to their majority compounds only, but it is probably due to a synergism between their chemical components. These results indicate that L. origanoides H.B.K. can be a source of phytochemicals able to modify the phenotype of resistance to aminoglycosides in MRSA.

The effect of Zuccagnia punctata, an Argentine medicinal plant, on virulence factors from candida species.

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Gabriela, Nuño; Rosa, Alberto María; Catiana, Zampini Iris; Soledad, Cuello; Mabel, Ordoñez Roxana; Esteban, Sayago Jorge; Veronica, Baroni; Daniel, Wunderlin; Ines, Isla María

2014-07-01

Zuccagnia punctata Cav. has been used as a traditional medicine in Argentina for the treatment of bacterial and fungal infections. In this study, we evaluated the ability of Z. punctata extract (ZpE) and compounds isolated from it to inhibit the growth and virulence factors of Candida species. ZpE showed inhibitory activity against planktonic cells of all assayed Candida species with MIC values of 400 microg/mL and with MFC values between 400 and 1,200 microg/mL. The principal identified compounds by HPLC-MS/MS and UV-VIS were chalcones (2',4'-dihydroxy-3'-methoxychalcone, 2',4'- dihydroxychalcone), flavones (galangin, 3,7-dihydroxyflavone and chrysin) and flavanones (naringenin, 7-hydroxyflavanone and pinocembrine). These compounds were more effective as inhibitors than the extracts upon biofilm formation as well as on preformed Candida biofilm and yeast germ tube formation. Furthermore, ZpE and chalcones are able to inhibit exoenzymes, which are responsible for the invasion mechanisms of the pathogens. All these effects could moderate colonization, thereby suppressing the pathogen invasive potential. Our results indicate that ZpE and chalcones could be used in antifungal therapy.

Phenolic Compounds Present Schinus terebinthifolius Raddi Influence the Lowering of Blood Pressure in Rats.

Science.gov (United States)

de Lima Glória, Lorena; Barreto de Souza Arantes, Mariana; Menezes de Faria Pereira, Silvia; de Souza Vieira, Guilherme; Xavier Martins, Camilla; Ribeiro de Carvalho Junior, Almir; Antunes, Fernanda; Braz-Filho, Raimundo; José Curcino Vieira, Ivo; Leandro da Cruz, Larissa; Siqueira de Almeida Chaves, Douglas; de Paiva Freitas, Silvério; Barros de Oliveira, Daniela

2017-10-23

This study identified two phenolic compounds in Schinus terebinthifolius Raddi fruits: naringenin (first report in this species) and gallic acid. Their structures were elucidated by nuclear magnetic resonance (NMR) data (¹H-, 13 C-NMR) and a high-performance liquid chromatography (HPLC) technique. A high content of phenolics (659.21 mg of gallic acid equivalents/g of sample-Folin-Ciocalteau method) and total flavonoids (140.69 mg of rutin equivalents/g of sample-aluminum chloride method) were quantified in S. terebinthifolius , as well as high antioxidant activity (77.47%-2,2-diphenyl-1-picrylhydrazyl, DPPH method). The antihypertensive activity related to its phenolic content was investigated. After intravenous infusion in Wistar rats, these phenolics significantly reduced ( p < 0.05) the systolic, median, and diastolic arterial pressures of individuals. The rotarod test was performed to determine the mechanism of action of the sample vasorelaxant effect. It was found that its action exceeded that of the positive control used (diazepam). This confirmed the vasodilatory activity exerted by S. terebinthifolius fruits is related to the phenolic compounds present in the plant, which are potent antioxidants and inhibit oxidative stress, mainly in the central nervous system.

SERS-Based Flavonoid Detection Using Ethylenediamine-β-Cyclodextrin as a Capturing Ligand

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Jae Min Choi

2017-01-01

Full Text Available Ethylenediamine-modified β-cyclodextrin (Et-β-CD was immobilized on aggregated silver nanoparticle (NP-embedded silica NPs (SiO2@Ag@Et-β-CD NPs for the effective detection of flavonoids. Silica NPs were used as the template for embedding silver NPs to create hot spots and enhance surface-enhanced Raman scattering (SERS signals. Et-β-CD was immobilized on Ag NPs to capture flavonoids via host-guest inclusion complex formation, as indicated by enhanced ultraviolet absorption spectra. The resulting SiO2@Ag@Et-β-CD NPs were used as the SERS substrate for detecting flavonoids, such as hesperetin, naringenin, quercetin, and luteolin. In particular, luteolin was detected more strongly in the linear range 10−7 to 10−3 M than various organic molecules, namely ethylene glycol, β-estradiol, isopropyl alcohol, naphthalene, and toluene. In addition, the SERS signal for luteolin captured by the SiO2@Ag@Et-β-CD NPs remained even after repeated washing. These results indicated that the SiO2@Ag@Et-β-CD NPs can be used as a rapid, sensitive, and selective sensor for flavonoids.

New Sulphated Flavonoids from Tamarix africana and Biological Activities of Its Polar Extract.

Science.gov (United States)

Karker, Manel; De Tommasi, Nunziatina; Smaoui, Abderrazak; Abdelly, Chedly; Ksouri, Riadh; Braca, Alessandra

2016-10-01

The phytochemical investigation of Tamarix africana Poir. (Tamaricaceae) shoot polar extract afforded three new sulphated flavonoids, (2 S ,4 R )-5,7,4'-trihydroxyflavan-4-ol 5,7-disulphate ( 1 ), (2 S )-5,7,4'-trihydroxyflavan 7- O -sulphate ( 2 ), and (2 S )-naringenin 4'- O -sulphate ( 3 ), together with ten known compounds. Their structures were determined by spectroscopic methods including 1D and 2D NMR analysis and HRMS. Biological activities of the polar extract of T. africana shoots related to its phenolic content were also investigated. A high total phenolic content (151.1 mg GAE/g) was found in the methanol shoot extract, which exhibits strong antioxidant activities using the oxygen radical absorbance capacity method and a skin cell-based assay. Moreover, the shoot extract showed significant anti-inflammatory activity, reducing nitric oxide release by 53.5 % at 160 µg/mL in lipopolysaccharide-stimulated RAW 264.7 macrophages. Finally, T. africana shoot extract inhibited the growth of A-549 lung carcinoma cells, with an IC 50 value of 34 µg/mL. Georg Thieme Verlag KG Stuttgart · New York.

Urinary metabolite profiling of flavonoids in Chinese volunteers after consumption of orange juice by UFLC-Q-TOF-MS/MS.

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Zeng, Xuan; Su, Weiwei; Bai, Yang; Chen, Taobin; Yan, Zenghao; Wang, Jiawei; Su, Minmin; Zheng, Yuying; Peng, Wei; Yao, Hongliang

2017-09-01

The metabolism of flavonoids derived from orange juice in Chinese volunteers has not been well investigated. With the ultra-fast liquid chromatography-quadrupole-time-of-flight tandem mass spectrometry (UFLC-Q-TOF-MS/MS) system, orange juice-derived flavonoids, as well as metabolites contained in urine collected from healthy Chinese volunteers after consumption of 250mL orange juice, were systematically identified and quantified. Finally, a total of 9 flavonoids and 30 metabolites were detected. Obtained results revealed that flavonoids derived from orange juice underwent extensive phase II metabolism in human, mainly comprising glucuronidation and sulfation. The overall recovery of the primary flavonoid aglycones, i.e., naringenin and hesperetin, were both approximately equivalent 22% of intake, primarily occurred in 4-12h post consumption. Meanwhile, additional 35 phenolic catabolites were identified in urine collected post consumption. However, it is difficult to determine the exact amounts of phenolic catabolites derived from specific flavonoid due to the interference of diets and other flavonoids. This work would be valuable for the clarification of metabolic profiles for flavonoids in Chinese population. Copyright © 2017 Elsevier B.V. All rights reserved.

Phenolic profiles of nectar and honey of Quillaja saponaria Mol. (Quillajaceae as potential chemical markers

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Gloria Montenegro

2013-01-01

Full Text Available Quillaja saponaria Mol. (Quillajaceae is one of the most important melliferous species in Chile, mainly as a source of monofloral honey. Honey made by A. mellifera presents biological activity against pathogens and antioxidant capacity associated with the presence of phenolic compounds deriving from the nectar, as a result of bee honey foraging. The aim of this study was to identify and quantify the phenolic compounds from the floral nectar of Q. saponaria and the honey made in apiaries in the central zone, and compare the composition of the chromatographic profiles of nectar and honey to known phenolic compounds. The results obtained by HPLC-DAD (high-performance liquid chromatography with diode-array detection showed a similar profile of phenolic compounds, in which gallic acid, myricetin, rutin, quercetin and naringenin were identified. The phenolic compounds detected could be used as a reference for future studies for determining potential chemical markers of this honey, complementing the present identification of honeys by determining their botanical origin. The identification of bioindicators of the floral origins for honey of this species could provide added value to honey commercialization by certifying the botanical origin of their chemical features and biological attributes.

Phenolic acid composition and antioxidant properties of Malaysian honeys.

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Khalil, M I; Alam, N; Moniruzzaman, M; Sulaiman, S A; Gan, S H

2011-08-01

The phenolic acid and flavonoid contents of Malaysian Tualang, Gelam, and Borneo tropical honeys were compared to those of Manuka honey. Ferric reducing/antioxidant power assay (FRAP) and the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical-scavenging activities were also quantified. All honey extracts exhibited high phenolic contents (15.21 ± 0.51- 42.23 ± 0.64 mg/kg), flavonoid contents (11.52 ± 0.27- 25.31 ± 0.37 mg/kg), FRAP values (892.15 ± 4.97- 363.38 ± 10.57 μM Fe[II]/kg), and high IC₅₀ of DPPH radical-scavenging activities (5.24 ± 0.40- 17.51 ± 0.51 mg/mL). Total of 6 phenolic acids (gallic, syringic, benzoic, trans-cinnamic, p-coumaric, and caffeic acids) and 5 flavonoids (catechin, kaempferol, naringenin, luteolin, and apigenin) were identified. Among the Malaysian honey samples, Tualang honey had the highest contents of phenolics, and flavonoids, and DPPH radical-scavenging activities. We conclude that among Malaysian honey samples, Tualang honey is the richest in phenolic acids, and flavonoid compounds, which have strong free radical-scavenging activities. © 2011 Institute of Food Technologists®

Nanocrystals of medium soluble actives--novel concept for improved dermal delivery and production strategy.

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Zhai, Xuezhen; Lademann, Jürgen; Keck, Cornelia M; Müller, Rainer H

2014-08-15

After use in oral pharmaceutical products, nanocrystals are meanwhile applied to improve the dermal penetration of cosmetic actives (e.g. rutin, hesperidin) and of drugs. By now, nanocrystals are only dermally applied made from poorly soluble actives. The novel concept is to formulate nanocrystals also from medium soluble actives, and to apply a dermal formulation containing additionally nanocrystals. The nanocrystals should act as fast dissolving depot, increase saturation solubility and especially accumulate in the hair follicles, to further increase skin penetration. Caffeine was used as model compound with relevance to market products, and a particular process was developed for the production of caffeine nanocrystals to overcome the supersaturation related effect of crystal growth and fiber formation - typical with medium soluble compounds. It is based on low energy milling (pearl milling) in combination with low dielectric constant dispersion media (water-ethanol or ethanol-propylene glycol mixtures) and optimal stabilizers. Most successful was Carbopol(®) 981 (e.g. 20% caffeine in ethanol-propylene glycol 3:7 with 2% Carbopol, w/w). Nanocrystals with varied sizes can now be produced in a controlled process e.g. 660 nm (optimal for hair follicle accumulation) to 250 nm (optimal for fast dissolution). The short term test proved stability over 2 months of the present formulation being sufficient to perform in vivo testing of the novel concept. Copyright © 2014 Elsevier B.V. All rights reserved.

Leaves of Cordia boissieri A. DC. as a potential source of bioactive secondary metabolites for protection against metabolic syndrome-induced in rats.

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Owis, Asmaa I; Abo-Youssef, Amira M; Osman, Ahmed H

2017-03-01

Cordia boissieri A. DC. (Boraginaceae) is traditionally used as an herbal remedy for diabetes by Hispanic women in Southwestern USA. A recent investigation showed the significant protective effect of ethyl acetate extract against metabolic syndrome (MS). However, the corresponding active principles responsible for this effect and relations between their structure and biological actions remain unclear. Thus, ethyl acetate extract was subjected to column chromatography, which yielded seven compounds identified on the basis of spectroscopic data as rutin, hesperidin, kaempferol-3-O-β-d-glucopyranoside, rosmarinic acid, β-sitosterol-3-O-β-d-glucopyranoside, quercetin, and kaempferol. The isolated compounds (5 mg/kg/day) were tested in a fructose enriched-diet rat model using metformin as a standard drug. Blood samples were withdrawn for estimation of MS-associated biomarkers and liver samples were subjected to histopathological and immunohistochemical examination. The isolated compounds impaired most of the changes associated with MS as evidenced by improved insulin sensitivity, glucose tolerance, kidney function, lipid profiles and reduced oxidative stress and inflammation by different degrees. It is worth noting that quercetin and kaempferol showed the most potent effect. Structure-activity relationship study revealed that the presence of 2,3-double bond in ring C and ortho-hydroxylation in ring B increases the flavonoids activity while glycosylation or methylation decreased this activity.

An Extract of Chinpi, the Dried Peel of the Citrus Fruit Unshiu, Enhances Axonal Remyelination via Promoting the Proliferation of Oligodendrocyte Progenitor Cells

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Hideaki Tokunaga

2016-01-01

Full Text Available The aging-induced decrease in axonal myelination/remyelination is due to impaired recruitment and differentiation of oligodendrocyte progenitor cells (OPCs. Our previous studies have shown that a monoclonal antibody to DEAD (Asp-Glu-Ala-Asp box polypeptide 54 (Ddx54, a member of the DEAD box family of RNA helicases, (1 specifically labels oligodendrocyte lineages, (2 binds to mRNA and protein isoforms of myelin basic proteins (MBP, and (3 regulates migration of OPCs from ventricular zone to corpus callosum in mice. It has also been demonstrated that specific loss of a 21.5 kDa MBP isoform (MBP21.5 reflects demyelination status, and oral administration of an extract of Chinpi, citrus unshiu peel, reversed the aging-induced demyelination. Here, we report that Chinpi treatment induced a specific increase in the MBP21.5, led to the reappearance of Ddx54-expressing cells in ventricular-subventricular zone and corpus callosum of aged mice, and promoted remyelination. Treatment of in vitro OPC cultures with Chinpi constituents, hesperidin plus narirutin, led to an increase in 5-bromo-2′-deoxyuridine incorporation in Ddx54-expressing OPCs, but not in NG2- or Olig2-expressing cell populations. The present study suggests that Ddx54 plays crucial role in remyelination. Furthermore, Chinpi and Chinpi-containing herbal medicines may be a therapeutic option for the aging-induced demyelination diseases.

Identification of a Multicomponent Traditional Herbal Medicine by HPLC-MS and Electron and Light Microscopy.

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Liu, Ju-Han; Cheng, Yung-Yi; Hsieh, Chen-Hsi; Tsai, Tung-Hu

2017-12-15

Commercial pharmaceutical herbal products have enabled people to take traditional Chinese medicine (TCM) in a convenient and accessible form. However, the quantity and quality should be additionally inspected. To address the issue, a combination of chemical and physical inspection methods were developed to evaluate the amount of an herbal formula, Xiang-Sha-Liu-Jun-Zi-Tang (XSLJZT), in clinical TCM practice. A high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS) method with electrospray ionization was developed to measure the herbal biomarkers of guanosine, atractylenolide III, glycyrrhizic acid, dehydrocostus lactone, hesperidin, and oleanolic acid from XSLJZT. Scanning electron microscopy (SEM) photographs and light microscopy photographs with Congo red and iodine-KI staining were used to identify the cellulose fibers and starch content. Furthermore, solubility analysis, swelling power test, and crude fiber analysis were contributed to measure the starch additive in pharmaceutical products. The results demonstrated large variations in the chemical components of different pharmaceutical brands. The SEM photographs revealed that the starch was oval, smooth, and granular, and that the raw herbal powder appears stripy, stretched, and filiform. The stained light microscopy photographs of all of the pharmaceutical products showed added starch and raw herbal powder as extenders. The developed chemical and physical methods provide a standard operating procedure for the quantity control of the herbal pharmaceutical products of XSLJZT.

Inhibitory effects of flavonoids on biofilm formation by Staphylococcus aureus that overexpresses efflux protein genes.

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Lopes, Laênia Angélica Andrade; Dos Santos Rodrigues, Jéssica Bezerra; Magnani, Marciane; de Souza, Evandro Leite; de Siqueira-Júnior, José P

2017-06-01

This study evaluated the efficacy of glycone (myricitrin, hesperidin and phloridzin) and aglycone flavonoids (myricetin, hesperetin and phloretin) in inhibiting biofilm formation by Staphylococcus aureus RN4220 and S. aureus SA1199B that overexpress the msrA and norA efflux protein genes, respectively. The minimum inhibitory concentration (MIC) and minimum biofilm inhibitory concentration (MBIC 50 - defined as the lowest concentration that resulted in ≥50% inhibition of biofilm formation) of flavonoids were determined using microdilution in broth procedures. The flavonoids showed MIC >1024 μg/mL against S. aureus RN4220 and S. aureus SA1199B; however, these compounds at lower concentrations (1-256 μg/mL) showed inhibitory effects on biofilm formation by these strains. Aglycone flavonoids showed lower MBIC 50 values than their respective glycone forms. The lowest MBIC 50 values (1 and 4 μg/mL) were observed against S. aureus RN4220. Myricetin, hesperetin and phloretin exhibited biofilm formation inhibition >70% for S. aureus RN4220, and lower biofilm formation inhibition against S. aureus SA1199B. These results indicate that sub-MICs of the tested flavonoids inhibit biofilm formation by S. aureus strains that overexpress efflux protein genes. These effects are more strongly established by aglycone flavonoids. Copyright © 2017 Elsevier Ltd. All rights reserved.

Evidence based research using phytochemicals as radioprotectors against ionizing-radiation

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Dey, Sanjit; Manna, Krishnendu; Khan, Amitava; Das, Ujjal; Biswas, Sushobhan; Sengupta, Aaveri

2016-01-01

Radiation is powerful physical phenomenon of mother nature. Planned use of radiation will increase in future as it is useful means for diagnosis and therapy. Conversely, humans face the threats of accidental exposures from radiation. Hence, development of appropriate evidence based radioprotectors should be in vogue. The current presentation will provide evidences on contribution of bioactive phytochemicals with definite chemical signatures as radioprotectors. The phytochemicals like quercetin, rutin, gossypetin, naringin, ferulic acid and shikimic acid prevented many events related to mitochondrial integrity and membrane polarization after radiation exposure, apart from systemic and cellular stresses. The radiation mediated authoritative cellular changes either in ex vivo or in vivo experiments. Radiation was responsible for augmentation of oxidative stress situation, promulgation of inflammation, DNA damage and promotion of apoptosis. On the other hand we found modulatory role of the phyto molecules favouring protection in terms of mitochondria dependant protein expressions of Mn-SOD, Bcl2, Bax, Cytochrome C along with prevention of mitochondrial integrity and membrane polarization alteration. Our results showed the radioprotection using plant bioactive compounds in terms of free radical scavenging abilities and maintenance of cellular antioxidant status using plant bioactive compounds. We concluded that the chemical structure-activity relationship of the phytocompounds restricts the cellular changes initiated by ionizing radiation with assertive involvement of specific subcellular signaling molecules. (author)

Bioactive Flavonoids, Antioxidant Behaviour, and Cytoprotective Effects of Dried Grapefruit Peels (Citrus paradisi Macf.)

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Castro-Vazquez, Lucia; Alañón, María Elena; Rodríguez-Robledo, Virginia; Pérez-Coello, María Soledad; Hermosín-Gutierrez, Isidro; Díaz-Maroto, María Consuelo; Jordán, Joaquín; Galindo, María Francisca; Arroyo-Jiménez, María del Mar

2016-01-01

Grapefruit (Citrus paradisi Macf.) is an important cultivar of the Citrus genus which contains a number of nutrients beneficial to human health. The objective of the present study was to evaluate changes in bioactive flavonoids, antioxidant behaviour, and in vitro cytoprotective effect of processed white and pink peels after oven-drying (45°C–60°C) and freeze-drying treatments. Comparison with fresh grapefruit peels was also assessed. Significant increases in DPPH, FRAPS, and ABTS values were observed in dried grapefruit peel samples in comparison with fresh peels, indicating the suitability of the treatments for use as tools to greatly enhance the antioxidant potential of these natural byproducts. A total of thirteen flavonoids were quantified in grapefruit peel extracts by HPLC-MS/MS. It was found that naringin, followed by isonaringin, was the main flavonoid occurring in fresh, oven-dried, and freeze-dried grapefruit peels. In vivo assay revealed that fresh and oven-dried grapefruit peel extracts (45°C) exerted a strong cytoprotective effect on SH-SY5Y neuroblastoma cell lines at concentrations ranging within 0.1–0.25 mg/mL. Our data suggest that grapefruit (Citrus paradisi Macf.) peel has considerable potential as a source of natural bioactive flavonoids with outstanding antioxidant activity which can be used as agents in several therapeutic strategies. PMID:26904169

Consumption of clarified grapefruit juice ameliorates high-fat diet induced insulin resistance and weight gain in mice.

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Chudnovskiy, Rostislav; Thompson, Airlia; Tharp, Kevin; Hellerstein, Marc; Napoli, Joseph L; Stahl, Andreas

2014-01-01

To determine the metabolic effects of grapefruit juice consumption we established a model in which C57Bl/6 mice drank 25-50% sweetened GFJ, clarified of larger insoluble particles by centrifugation (cGFJ), ad libitum as their sole source of liquid or isocaloric and sweetened water. cGFJ and control groups consumed similar amounts of liquids and calories. Mice fed a high-fat diet and cGFJ experienced a 18.4% decrease in weight, a 13-17% decrease in fasting blood glucose, a three-fold decrease in fasting serum insulin, and a 38% decrease in liver triacylglycerol values, compared to controls. Mice fed a low-fat diet that drank cGFJ experienced a two-fold decrease in fasting insulin, but not the other outcomes observed with the high-fat diet. cGFJ consumption decreased blood glucose to a similar extent as the commonly used anti-diabetic drug metformin. Introduction of cGFJ after onset of diet-induced obesity also reduced weight and blood glucose. A bioactive compound in cGFJ, naringin, reduced blood glucose and improved insulin tolerance, but did not ameliorate weight gain. These data from a well-controlled animal study indicate that GFJ contains more than one health-promoting neutraceutical, and warrant further studies of GFJ effects in the context of obesity and/or the western diet.

Atividade antimicrobiana de Schinus terebenthifolius Raddi Antimicrobial activity of Schinus terebenthifolius Raddi

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Cláudia Helena Degáspari

2005-06-01

Full Text Available Objetivou-se com este trabalho analisar a atividade antimicrobiana de extratos aquoso e alcoólico obtidos de frutos da Schinus terebenthifolius ou aroeira-vermelha, diretamente ligados à quantidade de compostos fenólicos existentes nesses extratos. Pelos testes, verificou-se que o extrato alcoólico apresentou efeito inibitório sobre o crescimento de Staphylococcus aureus e Bacillus cereus, já o extrato aquoso não apresentou efeito inibitório sobre os crescimento dos microrganismos testados. O extrato alcoólico mostrou-se com quantidade significativa da flavona apigenina, além de ácido elágico, ao passo que no extrato aquoso foi observada a presença da flavanona naringina.This research analyzed the antimicrobial activity of aqueous and alcoholic extracts obtained from Schinus terebenthifolius fruits or aroeira-vermelha, directly linked to the amount of phenolics compouds existent in these extracts. The tests showed that the alcoholic extract presented an inibitory effect to the growth of Staphylococcus aureus and Bacillus cereus, and the aqueous extract didn't present inibitory effect to the growth of the tested microorganisms. The alcoholic extract was shown with a significant amount of the flavone apigenin, besides ellagic acid and siringic acid, while in the aqueous extract was observed the flavanone naringine.

UVA-induced DNA double-strand breaks result from the repair of clustered oxidative DNA damages

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Greinert, R.; Volkmer, B.; Henning, S.; Breitbart, E. W.; Greulich, K. O.; Cardoso, M. C.; Rapp, Alexander

2012-01-01

UVA (320–400 nm) represents the main spectral component of solar UV radiation, induces pre-mutagenic DNA lesions and is classified as Class I carcinogen. Recently, discussion arose whether UVA induces DNA double-strand breaks (dsbs). Only few reports link the induction of dsbs to UVA exposure and the underlying mechanisms are poorly understood. Using the Comet-assay and γH2AX as markers for dsb formation, we demonstrate the dose-dependent dsb induction by UVA in G1-synchronized human keratinocytes (HaCaT) and primary human skin fibroblasts. The number of γH2AX foci increases when a UVA dose is applied in fractions (split dose), with a 2-h recovery period between fractions. The presence of the anti-oxidant Naringin reduces dsb formation significantly. Using an FPG-modified Comet-assay as well as warm and cold repair incubation, we show that dsbs arise partially during repair of bi-stranded, oxidative, clustered DNA lesions. We also demonstrate that on stretched chromatin fibres, 8-oxo-G and abasic sites occur in clusters. This suggests a replication-independent formation of UVA-induced dsbs through clustered single-strand breaks via locally generated reactive oxygen species. Since UVA is the main component of solar UV exposure and is used for artificial UV exposure, our results shine new light on the aetiology of skin cancer. PMID:22941639

Comparison of α-glucosyl hesperidin of citrus fruits and epigallocatechin gallate of green tea on the Loss of Rotavirus Infectivity in Cell Culture.

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Lipson, Steven M; Ozen, Fatma S; Louis, Samantha; Karthikeyan, Laina

2015-01-01

A number of secondary plant metabolites (e.g., flavonoids) possess antiviral/antimicrobial activity. Most flavonoids, however, are difficult to study, as they are immiscible in water-based systems. The relatively new semisynthetic α-glucosyl hesperitin (GH), and the natural plant product epigallocatechin gallate (EGCG) are unique among most flavonoids, as these flavonoids are highly soluble. The antiviral activity of these plant metabolites were investigated using the rotavirus as a model enteric virus system. Direct loss of virus structural integrity in cell-free suspension and titration of amplified RTV in host cell cultures was measured by a quantitative enzyme-linked immunosorbent assay (qEIA). After 30 min. 100 × 10(3) μg/ml GH reduced RTV antigen levels by ca. 90%. The same compound reduced infectivity (replication in cell culture) by a similar order of magnitude 3 to 4 days post inoculation. After 3 days in culture, EGCG concentrations of 80, 160, and 320 μg/ml reduced RTV infectivity titer levels to ca. 50, 20, and 15% of the control, respectively. Loss of RTV infectivity titers occurred following viral treatment by parallel testing of both GH and EGCG, with the latter, markedly more effective. Cytotoxicity testing showed no adverse effects by the phenolic concentrations used in this study. The unique chemical structure of each flavonoid rather than each phenolic's inherent solubility may be ascribed to those marked differences between each molecule's antiviral (anti-RTV) effects. The solubility of EGCG and GH obviated our need to use potentially confounding or obfuscating carrier molecules (e.g., methanol, ethanol, DMSO) denoting our use of a pure system environ. Our work further denotes the need to address the unique chemical nature of secondary plant metabolites before any broad generalizations in flavonoid (antiviral) activity may be proposed.

A new bioactive monoterpene-flavonoid from Satureja khuzistanica.

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Malmir, Maryam; Gohari, Ahmad Reza; Saeidnia, Soodabeh; Silva, Olga

2015-09-01

A new monoterpene-flavonoid, saturejin (3'-(2,5-dihydroxy-p-cymene) 5,7,4'-trihydroxy flavone) (4), together with twelve known flavonoids consist of two flavanonols (aromadendrin (8) and taxifolin (12)), two flavanones (naringenin (3) and 5,7,3',5'-tetrahydroxy flavanone (9)) and eight flavones (xanthomicrol (1), acacetin (2), cirsimaritin (5), 7-methoxy luteolin (6), apigenin (7), cirsilineol (10), diosmetin (11) and 6-hydroxyluteolin 7,3'-dimethyl ether (13)), were isolated from an ethyl acetate extract and identified for the first time in the dried aerial parts of Satureja khuzistanica Jamzad, an endemic medicinal plant traditionally used as dental anesthetic, oral antiseptic and anti-inflammatory among the nomadic inhabitants of southwestern Iran. The structures of these compounds were determined using the usual spectroscopic methods including 2D-NMR and MS analyses. Saturejin showed a significant β-glucosidase inhibitory activity at concentration of 10 μg as well as positive antioxidant activity at the amount of 1 μg. These results could be correlated with the in vitro and in vivo anti-inflammatory, anti-oxidant and anti-diabetic properties reported from this medicinal plant. Similar activities were also described for some of the other isolated compounds. Copyright © 2015 Elsevier B.V. All rights reserved.

Characterization of three chalcone synthase-like genes from apple (Malus x domestica Borkh.).

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Yahyaa, Mosaab; Ali, Samah; Davidovich-Rikanati, Rachel; Ibdah, Muhammad; Shachtier, Alona; Eyal, Yoram; Lewinsohn, Efraim; Ibdah, Mwafaq

2017-08-01

Apple (Malus x domestica Brokh.) is a widely cultivated deciduous tree species of significant economic importance. Apple leaves accumulate high levels of flavonoids and dihydrochalcones, and their formation is dependent on enzymes of the chalcone synthase family. Three CHS genes were cloned from apple leaves and expressed in Escherichia coli. The encoded recombinant enzymes were purified and functionally characterized. In-vitro activity assays indicated that MdCHS1, MdCHS2 and MdCHS3 code for proteins exhibiting polyketide synthase activity that accepted either p-dihydrocoumaroyl-CoA, p-coumaroyl-CoA, or cinnamoyl-CoA as starter CoA substrates in the presence of malonyl-CoA, leading to production of phloretin, naringenin chalcone, and pinocembrin chalcone. MdCHS3 coded a chalcone-dihydrochalcone synthase enzyme with narrower substrate specificity than the previous ones. The apparent Km values of MdCHS3 for p-dihydrocoumaryl-CoA and p-coumaryl-CoA were both 5.0 μM. Expression analyses of MdCHS genes varied according to tissue type. MdCHS1, MdCHS2 and MdCHS3 expression levels were associated with the levels of phloretin accumulate in the respective tissues. Copyright © 2017 Elsevier Ltd. All rights reserved.

Genome-Wide Comparison of Magnaporthe Species Reveals a Host-Specific Pattern of Secretory Proteins and Transposable Elements.

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Meghana Deepak Shirke

Full Text Available Blast disease caused by the Magnaporthe species is a major factor affecting the productivity of rice, wheat and millets. This study was aimed at generating genomic information for rice and non-rice Magnaporthe isolates to understand the extent of genetic variation. We have sequenced the whole genome of the Magnaporthe isolates, infecting rice (leaf and neck, finger millet (leaf and neck, foxtail millet (leaf and buffel grass (leaf. Rice and finger millet isolates infecting both leaf and neck tissues were sequenced, since the damage and yield loss caused due to neck blast is much higher as compared to leaf blast. The genome-wide comparison was carried out to study the variability in gene content, candidate effectors, repeat element distribution, genes involved in carbohydrate metabolism and SNPs. The analysis of repeat element footprints revealed some genes such as naringenin, 2-oxoglutarate 3-dioxygenase being targeted by Pot2 and Occan, in isolates from different host species. Some repeat insertions were host-specific while other insertions were randomly shared between isolates. The distributions of repeat elements, secretory proteins, CAZymes and SNPs showed significant variation across host-specific lineages of Magnaporthe indicating an independent genome evolution orchestrated by multiple genomic factors.

Phytochemical Profile, Chemotaxonomic Studies, and In Vitro Antioxidant Activities of Two Endemisms from Madeira Archipelago: Melanoselinum decipiens and Monizia edulis (Apiaceae).

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Spínola, Vítor; Castilho, Paula C

2016-10-01

Melanoselinum decipiens and Monizia edulis (Apiaceae) are two endemic plants from Madeira archipelago, phytochemical compositions of which remains little explored, despite their use in folk medicine. Using liquid chromatography with diode array and electrospray ionization/mass spectrometry analysis, their polyphenolic profile was established for the first time. Fifty-six compounds were identified with 5-O-caffeoylquinic acid, quercetin-O-(malonyl)hexoside, luteolin diacetyl, and quercetin-O-hexoside being the major constituents in the leaves of both plant species (≥ 0.76 mg/g of dry extract). Principal component analysis provided a suitable tool to differentiate targeted plants. Naringenin-6,8-di-C-glucoside, quercetin 3-O-pentosylhexoside, and 1,5-O-dicaffeoylquinic acid can be used as discriminatory taxonomic/geographical markers for M. edulis subspecies from Madeira and Porto Santo populations. This methodology of using polyphenols as chemotaxonomic markers proved to be useful for identification of plant species since the results are consistent with previous taxonomical data. The free-radical scavenging activities of the M. decipiens extracts proved to be higher than those of M. edulis, which correlated well with their phenolic content (R 2  > 0.906). © 2016 Wiley-VHCA AG, Zürich.

Recent development in antihyperalgesic effect of phytochemicals: anti-inflammatory and neuro-modulatory actions.

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Singh, Ajeet Kumar; Kumar, Sanjay; Vinayak, Manjula

2018-05-16

Pain is an unpleasant sensation triggered by noxious stimulation. It is one of the most prevalent conditions, limiting productivity and diminishing quality of life. Non steroidal anti inflammatory drugs (NSAIDs) are widely used as pain relievers in present day practice as pain is mostly initiated due to inflammation. However, due to potentially serious side effects, long term use of these antihyperalgesic drugs raises concern. Therefore there is a demand to search novel medicines with least side effects. Herbal products have been used for centuries to reduce pain and inflammation, and phytochemicals are known to cause fewer side effects. However, identification of active phytochemicals of herbal medicines and clear understanding of the molecular mechanism of their action is needed for clinical acceptance. In this review, we have briefly discussed the cellular and molecular changes during hyperalgesia via inflammatory mediators and neuro-modulatory action involved therein. The review includes 54 recently reported phytochemicals with antihyperalgesic action, as per the literature available with PubMed, Google Scholar and Scopus. Compounds of high interest as potential antihyperalgesic agents are: curcumin, resveratrol, capsaicin, quercetin, eugenol, naringenin and epigallocatechin gallate (EGCG). Current knowledge about molecular targets of pain and their regulation by these phytochemicals is elaborated and the scope of further research is discussed.

Some bioactive compounds and antioxidant activities of the bitter almond kernel (prunus dulcis var. amara)

International Nuclear Information System (INIS)

Keser, S.; Yilmaz, O.

2014-01-01

in this study, it was determined antioxidant activities and phenolic, flavonoid, phytosterol, lipid soluble vitamin and fatty acid contents of bitter almond kernel extract (bae). antioxidant activities of bae was investigated by dppho, abtso+, oho radical scavenging, metal chelating activity and determination of lipid peroxidation levels (tbars). bae was scavenged 83.49% of the abts radical, 68.34% of the hydroxyl radical, and 68.65% of the dpph radical. this extract was shown 49.36% of the metal chelating activity myricetin (1831.52 mu g/g), kaempferol (104.52 mu g/g), naringenin (2.51 mu g/g), vanillic acid (91.70 mu g/g), caffeic acid (85.92 mu g/g), ferulic acid (27.11 mu g/g) rosmarinic acid (0.95 mu g/g), hydroxycinnamic acid (1.35 mu g/g), delta-tocopherol (4.95 mg/kg), mu-tocopherol (104.15 mg/kg), vitamin k (42.25 mg/kg), beta-sitosterol (366.95 mg/kg) and stigmasterol (242.65 mg/kg) were determined in the bae. the major fatty acids were oleic acid (70.61%) and linoleic acid (20.68%) in the bae. these results indicate that bitter almond can be a good natural source of fatty acids, lipid soluble vitamins, phytosterols, flavonoid, phenolic compounds. (author)

A theoretical assessment of antioxidant capacity of flavonoids by means of local hyper–softness

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Claudia Sandoval-Yañez

2018-05-01

Full Text Available A theoretical reactivity descriptor to estimate local reactivity on molecules was tested to assess the antioxidant capability of some flavonoids. It was validated by comparison with experimental precedents published already by Firuzi et al. (2005. The aforementioned reactivity index is called local hyper-softness (LHS. This parameter was applied on HO- substituent groups on the same set of flavonoids within each subclassification: flavones (apigenin and baicalein, flavonols (fisetin, galangin, 3–OH flavone, kaempferol, myricetin, and quercetin, flavanones (hesperetin, naringenin, taxifolin and isoflavones (daidzein and genistein. Experimental values of both techniques, ferric reducing antioxidant power (FRAP and anodic oxidation potential (Eap were retrieved from Firuzi et al. (2005 with the purpose of validating the calculated LHS values. Excepting myricetin, the LHS values of all these compounds matched in a similar order relationship experimentally obtained by means of Eap and FRAP from Firuzi et al. (2005. Our results revealed that LHS is a suitable theoretical parameter to get an insight concerning to the antioxidant capacity of these compounds, in particular, LHS allows explaining experimentally obtained values of FRAP along with Eap values in terms of reactivity of HO- substituent groups belonging these molecules theoretically computed without including experimental parametes. Keywords: Flavonoids, Antioxidant capacity, Ferric reducing antioxidant power, Anodic oxidation potential, Local hypersoftness

Functional Characterization of a Flavonoid Glycosyltransferase in Sweet Orange (Citrus sinensis).

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Liu, Xiaogang; Lin, Cailing; Ma, Xiaodi; Tan, Yan; Wang, Jiuzhao; Zeng, Ming

2018-01-01

Fruits of sweet orange ( Citrus sinensis ), a popular commercial Citrus species, contain high concentrations of flavonoids beneficial to human health. These fruits predominantly accumulate O -glycosylated flavonoids, in which the disaccharides [neohesperidose (rhamnosyl-α-1,2-glucose) or rutinose (rhamnosyl-α-1,6-glucose)] are linked to the flavonoid aglycones through the 3- or 7-hydroxyl sites. The biotransformation of the flavonoid aglycones into O -rutinosides or O -neohesperidosides in the Citrus plants usually consists of two glycosylation reactions involving a series of uridine diphosphate-sugar dependent glycosyltransferases (UGTs). Although several genes encoding flavonoid UGTs have been functionally characterized in the Citrus plants, full elucidation of the flavonoid glycosylation process remains elusive. Based on the available genomic and transcriptome data, we isolated a UGT with a high expression level in the sweet orange fruits that possibly encodes a flavonoid glucosyltransferase and/or rhamnosyltransferase. Biochemical analyses revealed that a broad range of flavonoid substrates could be glucosylated at their 3- and/or 7-hydrogen sites by the recombinant enzyme, including hesperetin, naringenin, diosmetin, quercetin, and kaempferol. Furthermore, overexpression of the gene could significantly increase the accumulations of quercetin 7- O -rhamnoside, quercetin 7- O -glucoside, and kaempferol 7- O -glucoside, implying that the enzyme has flavonoid 7- O -glucosyltransferase and 7- O -rhamnosyltransferase activities in vivo .

UFLC-Q-TOF-MS/MS-Based Screening and Identification of Flavonoids and Derived Metabolites in Human Urine after Oral Administration of Exocarpium Citri Grandis Extract

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Xuan Zeng

2018-04-01

Full Text Available Exocarpium Citri grandis (ECG is an important Traditional Chinese Medicine (TCM for the treatment of cough and phlegm, and the flavonoids contained were considered the main effective components. To date, the systematic chemical profiling of these flavonoids and derived in vivo metabolites in human have not been well investigated. ECG was extracted using boiling water and then provided to volunteers for oral administration. Following the ingestion, urine samples were collected from volunteers over 48 h. The extract and urine samples were analyzed using ultra-fast liquid chromatography/quadrupole-time-of-flight tandem mass spectrometry (UFLC-Q-TOF-MS/MS system to screen and identify flavonoids and derived in vivo metabolites. A total of 18 flavonoids were identified in the ECG extract, and 20 metabolites, mainly glucuronide and sulfate conjugates, were screened in urine samples collected post consumption. The overall excretion of naringenin metabolites corresponded to 5.45% of intake and occurred mainly within 4–12 h after the ingestion. Meanwhile, another 29 phenolic catabolites were detected in urine. Obtained data revealed that flavonoids were abundant in the ECG extract, and these components underwent extensive phase II metabolism in humans. These results provided valuable information for further study of the pharmacology and mechanism of action of ECG.

The Sorghum Gene for Leaf Color Changes upon Wounding (P Encodes a Flavanone 4-Reductase in the 3-Deoxyanthocyanidin Biosynthesis Pathway

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Hiroyuki Kawahigashi

2016-05-01

Full Text Available Upon wounding or pathogen invasion, leaves of sorghum [Sorghum bicolor (L. Moench] plants with the P gene turn purple, whereas leaves with the recessive allele turn brown or tan. This purple phenotype is determined by the production of two 3-deoxyanthocyanidins, apigeninidin and luteolinidin, which are not produced by the tan-phenotype plants. Using map-based cloning in progeny from a cross between purple Nakei-MS3B (PP and tan Greenleaf (pp cultivars, we isolated this gene, which was located in a 27-kb genomic region around the 58.1 Mb position on chromosome 6. Four candidate genes identified in this region were similar to the maize leucoanthocyanidin reductase gene. None of them was expressed before wounding, and only the Sb06g029550 gene was induced in both cultivars after wounding. The Sb06g029550 protein was detected in Nakei-MS3B, but only slightly in Greenleaf, in which it may be unstable because of a Cys252Tyr substitution. A recombinant Sb06g029550 protein had a specific flavanone 4-reductase activity, and converted flavanones (naringenin or eriodictyol to flavan-4-ols (apiforol or luteoforol in vitro. Our data indicate that the Sb06g029550 gene is involved in the 3-deoxyanthocyanidin synthesis pathway.

Correlation between the potency of flavonoids for cytochrome c reduction and inhibition of cardiolipin-induced peroxidase activity.

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Lagoa, Ricardo; Samhan-Arias, Alejandro K; Gutierrez-Merino, Carlos

2017-05-06

There are large differences between flavonoids to protect against apoptosis, a process in which cytochrome c (Cyt c) plays a key role. In this work, we show that 7 of 13 flavonoids studied have a capacity to reduce Cyt c similar or higher than ascorbate, the flavonols quercetin, kaempferol and myricetin, flavanol epigallocatechin-gallate, anthocyanidins cyanidin and malvidin, and the flavone luteolin. In contrast, the kaempferol 3(O)- and 3,4'(O)-methylated forms, the flavanone naringenin, and also apigenin and chrysin, had a negligible reducing capacity. Equilibrium dialysis and quenching of 1,6-diphenyl-1,3,5-hexatriene fluorescence experiments showed that flavonoids did not interfere with Cyt c binding to cardiolipin (CL)/phosphatidylcholine (PC) vesicles. However, the CL-induced loss of Cyt c Soret band intensity was largely attenuated by flavonoids, pointing out a stabilizing action against Cyt c unfolding in the complex. Moreover, flavonoids that behave as Cyt c reductants also inhibited the pro-apoptotic CL-induced peroxidase activity of Cyt c, indicating that modulation of Cyt c signaling are probable mechanisms behind the protective biological activities of flavonoids. © 2016 BioFactors, 43(3):451-468, 2017. © 2017 International Union of Biochemistry and Molecular Biology.

Investigation of Interactions between Thrombin and Ten Phenolic Compounds by Affinity Capillary Electrophoresis and Molecular Docking

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Qiao-Qiao Li

2018-01-01

Full Text Available Thrombin plays a vital role in blood coagulation, which is a key process involved in thrombosis by promoting platelet aggregation and converting fibrinogen to form the fibrin clot. In the receptor concept, drugs produce their therapeutic effects via interactions with the targets. Therefore, investigation of interaction between thrombin and small molecules is important to find out the potential thrombin inhibitor. In this study, affinity capillary electrophoresis (ACE and in silico molecular docking methods were developed to study the interaction between thrombin and ten phenolic compounds (p-hydroxybenzoic acid, protocatechuic acid, vanillic acid, gallic acid, catechin, epicatechin, dihydroquercetin, naringenin, apigenin, and baicalein. The ACE results showed that gallic acids and six flavonoid compounds had relative strong interactions with thrombin. In addition, the docking results indicated that all of optimal conformations of the six flavonoid compounds were positioned into the thrombin activity centre and had interaction with the HIS57 or SER195 which was the key residue to bind thrombin inhibitors such as argatroban. Herein, these six flavonoid compounds might have the potential of thrombin inhibition activity. In addition, the developed method in this study can be further applied to study the interactions of other molecules with thrombin.

Influence of Ripeness and Drying Process on the Polyphenols and Tocopherols of Pistacia vera L.

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Gabriele Ballistreri

2009-10-01

Full Text Available This paper highlights, for the first time, the changes in the phenolics fraction (anthocyanins, flavonoids and stilbenes and tocopherols of unpeeled Pistacia vera L. var. bianca with ripening, and the effect of the sun-drying process. The total polyphenol levels in pistachios, measured as mg of Gallic Acid Equivalent (GAE, were: 201 ± 10.1, 349 ± 18.3 and 184.7 ± 6.2 mg GAE/100 g DM in unripe, ripe and dried ripe samples, respectively. Most phenolics in ripe pistachios were found to be anthocyanins. They increased with ripening, while the sun drying process caused a susbtantial loss. Flavonoids found in all pistachio samples were daidzein, genistein, daidzin, quercetin, eriodictyol, luteolin, genistin and naringenin, which decreased both with ripening and drying. Before the drying process both unripe and ripe pistachios showed a higher content of trans-resveratrol than dried ripe samples. γ-Tocopherol was the major vitamin E isomer found in pistachios. The total content (of α- and γ-tocopherols decreased, both during ripening and during the drying process. These results suggested that unpeeled pistachios can be considered an important source of phenolics, particularly of anthocyanins. Moreover, in order to preserve these healthy characteristics, new and more efficient drying processes should be adopted.

Hesperitin derivative-11 suppress hepatic stellate cell activation and proliferation by targeting PTEN/AKT pathway

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Li, Wan-xia; Chen, Xin; Yang, Yang; Huang, Hui-min; Li, Hai-di; Huang, Cheng; Meng, Xiao-ming; Li, Jun

2017-01-01

Hesperitin derivative (HD-11) is a monomeric compound derived from Hesperidin, which is a naturally occurring flavanone glycoside that exerts extensive clinical effects such as anti-inflammatory, anti-oxidant and anti-angiogenic. However, the role and fundamental mechanism of HD-11 in hepatic fibrosis are still unrevealed. In this study, HD-11 not only alleviates ECM deposition in rats with liver fibrosis, but also reduces the expression of α-SMA and col1a1 in TGF-β1-induced HSC-T6 cells. Moreover, it was demonstrated that HD-11 significantly promoted the expression of PTEN in vivo and in vitro. In order to evaluate the involvement of HD-11 in TGF-β1-induced HSC-T6 activation, a specific blocking agent of PTEN (bpv) and PTEN small interfering (si)-RNA-mediated silencing were used. Interestingly, HD-11 treatment couldn’t inhibit α-SMA and col1a1 expression on the basis of PTEN knockdown. On the contrary, over-expression of PTEN had an opposite effect on the expression of α-SMA and col1a1 in TGF-β1-induced HSC-T6 cells after treatment of HD-11. In addition, HD-11 remarkably inhibited the expression of p-AKT in vivo and in vitro. Taken together, all the above results indicate that HD-11 may play the part of an effective modulator of PTEN/AKT signaling pathway.

The protective effect of hesperetin and nano-hesperetin on object recognition memory in animal model of Alzheimer

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2017-11-01

Full Text Available Background and objectives: Hesperetin (Hst, aglycone form of hesperidin, is reported to have antioxidant, anti-inflammatory and neuroprotective activities. On the other hand, the latest nanoparticle technology can help to improve the bioavailability of Hst, which is affected by the final particle size and stability. Alzheimer’s disease is a neurodegenerative disease, characterized by loss of the cognitive abilities, including memory, speech, emotions, and personality. Oxidative stress, a condition that occurs due to the imbalance in oxidant and antioxidant status, has been known to play a vital role in the pathophysiology of neurodegenerative diseases. This study was carried out in order to evaluate the protective effects of hesperetin and nano-hesperetin on memory disorder in the brains of Alzheimer’s animal models. Methods: Forty nine male rats were divided into 7 groups: control, vehicle, STZ group (rats were injected with STZ, treatment groups receiving 10 and 20 mg/kg/day of hesperetin and nano-hesperetin. Then 3 μgr/rat of (STZ was injected to the cerebroventricular of rats of all groups except the control and vehicle groups. The 4 treatment groups were gavaged by, respectively 10, 20 mg/Kg of hesperetin and nano-hesperetin for 30 days. After three weeks, recognition memory was examined by novel object recognition test. Results: The results showed that injection of STZ increased memory disorders (p≤0.001 and treatment of hesperetin and nano-hesperetin effectively decreased memory disorders (p

Glycine tomentella Hayata inhibits IL-1β and IL-6 production, inhibits MMP-9 activity, and enhances RAW264.7 macrophage clearance of apoptotic cells

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Sun Yu-Shu

2010-11-01

Full Text Available Abstract Background To assess the effects of Glycine tomentella Hayata (GTH, a traditional herbal medicine for treatment of rheumatic diseases on the expression of the proinflammatory cytokines and on the clearance of apoptotic cells by macrophages. Methods RAW264.7 cells were cultured with lipopolysaccharide (LPS in the presence or absence of ethanol extract of GTH. The expression of proinflammatory cytokines IL-1β, IL-6, and TNF-α, and inducible nitric oxide synthase (iNOS and transglutaminase 2 (TG2 were assayed by reverse transcriptase-polymerase chain reaction (RT-PCR and enzyme-linked immunosorbent assay (ELISA. Matrix metalloproteinase (MMP-2 and MMP-9 were assayed by gelatin zymography. For detecting uptake of apoptotic cells, RAW264.7 cells were cultured with carboxyfluorescein diacetate (CFDA-stained apoptotic cells and assayed by flow cytometry. Results The major components of GTH analyzed by high-performance liquid chromatography (HPLC chromatogram were daidzein (42.5%, epicatechin (28.8%, and naringin (9.4%. GTH treatment inhibited the expression of proinflammatory cytokines IL-1β, IL-6 and MMP-9 but did not affect the expression of TNF-α and iNOS. GTH significantly enhanced the expression of TG2 and the clearance of apoptotic cells by RAW264.7 macrophages. Conclusions GTH inhibits proinflammatory cytokine secretion and MMP-9 activity, enhances apoptotic cell uptake and up-regulates TG2 expression. Our data show that GTH might have beneficial effects on rheumatic diseases.

Antioxidant and Anti-quorum Sensing Potential of Acer monspessulanum subsp. monspessulanum Extracts.

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Ceylan, Ozgur; Sahin, Mehtap Donmez; Akdamar, Gultekin

2016-10-01

In this study, anti-quorum sensing, and antioxidant activities, and chemical composition of Acer monspessulanum subsp. monspessulanum extracts were evaluated. Determination of the antioxidant activity was revealed by DPPH radical scavenging activity, the total phenolic content assay, and the β -carotene/linoleic acid assay. The detection of phenolic compounds was determined using RP-HPLC. Anti-quorum sensing activity and violacein inhibition activity were determined using Chromobacterium violaceum CV026 and C. violaceum ATCC 112 472, respectively. The determination of anti-swarming activity was carried out with Pseudomonas aeruginosa PA01. In DPPH and total phenolic content assays, the water extract exhibited good antioxidant activity. In the β -carotene-linoleic acid assay, ethyl acetate and ethanol extracts exhibited good lipid peroxidation inhibition activity, demonstrating 96.95 ± 0.03 % and 95.35 ± 0.00 % at 2.5 mg/mL concentrations, respectively. The predominant phenolic compounds of the extracts were determined as rutin, naringin, catechin hydrate, quercetin, and protocatechuic acid. Ethyl acetate and ethanol extracts were found to contain a high level of violacein inhibition and anti-quorum sensing activity. The ethanol extract also showed weak anti-swarming activity. In this first study that used Acer monspessulanum subsp. monspessulanum extracts, it was revealed that the water extract has antioxidant activity and the ethanol and ethyl acetate extracts have anti-quorum sensing activity depending on the phenolic compounds that it contained. Georg Thieme Verlag KG Stuttgart · New York.

HMG-CoA reductase inhibitory activity and phytocomponent investigation of Basella alba leaf extract as a treatment for hypercholesterolemia

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Baskaran G

2015-01-01

Full Text Available Gunasekaran Baskaran,1 Shamala Salvamani,1 Siti Aqlima Ahmad,1 Noor Azmi Shaharuddin,1 Parveen Devi Pattiram,2 Mohd Yunus Shukor1 1Department of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, 2Department of Food Technology, Faculty of Food Science and Technology, Universiti Putra Malaysia, Selangor, Malaysia Abstract: The enzyme 3-hydroxy-3-methyl-glutaryl-coenzyme A (HMG-CoA reductase is the key enzyme of the mevalonate pathway that produces cholesterol. Inhibition of HMG-CoA reductase reduces cholesterol biosynthesis in the liver. Synthetic drugs, statins, are commonly used for the treatment of hypercholesterolemia. Due to the side effects of statins, natural HMG-CoA reductase inhibitors of plant origin are needed. In this study, 25 medicinal plant methanol extracts were screened for anti-HMG-CoA reductase activity. Basella alba leaf extract showed the highest inhibitory effect at about 74%. Thus, B. alba was examined in order to investigate its phytochemical components. Gas chromatography with tandem mass spectrometry and reversed phase high-performance liquid chromatography analysis revealed the presence of phenol 2,6-bis(1,1-dimethylethyl, 1-heptatriacotanol, oleic acid, eicosyl ester, naringin, apigenin, luteolin, ascorbic acid, and a-tocopherol, which have been reported to possess antihypercholesterolemic effects. Further investigation of in vivo models should be performed in order to confirm its potential as an alternative treatment for hypercholesterolemia and related cardiovascular diseases. Keywords: HMG-CoA reductase, Basella alba, phytochemical, GC-MS/MS, RP-HPLC, hypercholesterolemia

Phytochemical constituents, antioxidant activity and toxicity potential of Phlomis olivieri Benth.

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M.R. Delnavazi

2016-04-01

Full Text Available Background and objectives: Phlomis olivieri Benth. (Lamiaceae is a medicinal plant widely distributed in Iran. In the present study, we have investigated the phytochemical constituents, antioxidant activity and general toxicity potential of the aerial parts of this species. Methods: Silica gel (normal and reversed phases and Sephadex LH-20 column chromatographies were used for isolation of compounds from methanol-soluble portion (MSP of the total extract obtained from P. olivieri aerial parts. The structures of isolated compounds were elucidated using 1H-NMR, 13C-NMR and UV spectral analyses. Antioxidant activity and general toxicity potential of MSP were also evaluated in DPPH free radical-scavenging assay and brine shrimp lethality test (BSLT, respectively. Results: One caffeoylquinic acid derivative, chlorogenic acid (1, one iridoid glycoside, ipolamiide (2, two phenylethanoid glycosides, phlinoside C (3 and verbascoside (5, along with two flavonoids, isoquercetin (4 and naringenin (6 were isolated and identified from MSP. The MSP exhibited considerable antioxidant activity in DPPH method (IC50; 50.4 ± 4.6 µg/mL, compared to BHT (IC50; 18.7 ± 2.1 µg/mL, without any toxic effect in BSLT at the highest tested dose (1000 µg/mL. Conclusion: the results of the present study introduce P. olivieri as a medicinal plant with valuable biological and pharmacological potentials.

p-Coumaric acid enhances long-term potentiation and recovers scopolamine-induced learning and memory impairments.

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Kim, Hyun-Bum; Lee, Seok; Hwang, Eun-Sang; Maeng, Sungho; Park, Ji-Ho

2017-10-21

Due to the improvement of medical level, life expectancy increased. But the increased incidence of cognitive disorders is an emerging social problem. Current drugs for dementia treatment can only delay the progress rather than cure. p-Coumaric acid is a phenylpropanoic acid derived from aromatic amino acids and known as a precursor for flavonoids such as resveratrol and naringenin. It was shown to reduce oxidative stress, inhibit genotoxicity and exert neuroprotection. Based on these findings, we evaluated whether p-coumaric acid can protect scopolamine induced learning and memory impairment by measuring LTP in organotypic hippocampal slice and cognitive behaviors in rats. p-Coumaric acid dose-dependently increased the total activity of fEPSP after high frequency stimulation and attenuated scopolamine-induced blockade of fEPSP in the hippocampal CA1 area. In addition, while scopolamine shortened the step-through latency in the passive avoidance test and prolonged the latency as well as reduced the latency in the target quadrant in the Morris water maze test, co-treatment of p-coumaric acid improved avoidance memory and long-term retention of spatial memory in behavioral tests. Since p-coumaric acid improved electrophysiological and cognitive functional deterioration by scopolamine, it may have regulatory effects on central cholinergic synapses and is expected to improve cognitive problems caused by abnormality of the cholinergic nervous system. Copyright © 2017 Elsevier Inc. All rights reserved.

Effects of unripe Citrus hassaku fruits extract and its flavanone glycosides on blood fluidity.

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Itoh, Kimihisa; Masuda, Megumi; Naruto, Shunsuke; Murata, Kazuya; Matsuda, Hideaki

2010-01-01

The enhancement of blood fluidity may lead to improvements in skin problems resulting from unsmooth circulation or blood stagnation. Since a 50% ethanolic extract (CH-ext) obtained from unripe Citrus hassaku fruits may be a useful ingredient in skin-whitening cosmetics, the present study was designed to examine the effect of CH-ext on blood fluidity. CH-ext concentration-dependently inhibited in vitro collagen-induced rabbit platelet aggregation and in vitro polybrene-induced rat erythrocyte aggregation. The CH-ext showed in vitro fibrinolysis activity in fibrin plate assay. Activity-guided fractionation of the CH-ext using antiplatelet activity, inhibitory activity of erythrocyte aggregation, and fibrinolysis activity revealed that these activities of CH-ext were attributable to naringenin-7-glycoside (prunin). Successive oral administration of CH-ext to rats inhibited the lipopolysaccharide (LPS)-induced decrease of blood platelets and fibrinogen, and LPS-induced increase of fibrin degradation products (FDP) in LPS-induced disseminated intravascular coagulation (DIC) model rats. Effects of CH-ext on blood fluidity were analyzed by a micro channel array flow analyzer (MC-FAN). Preventive oral administration of CH-ext to rats showed dose-dependent reduction of the passage time of whole blood flow of the DIC model rats in comparison with that of the vehicle control rats. These results imply that CH-ext may have effects which improve effects on blood fluidity.

Identification of phenolic acids and flavonoids in monofloral honey from Bangladesh by high performance liquid chromatography: determination of antioxidant capacity.

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Moniruzzaman, Mohammed; Yung An, Chua; Rao, Pasupuleti Visweswara; Hawlader, Mohammad Nurul Islam; Azlan, Siti Amirah Binti Mohd; Sulaiman, Siti Amrah; Gan, Siew Hua

2014-01-01

The aim of the present study was to characterize the phenolic acids, flavonoids, and antioxidant properties of monofloral honey collected from five different districts in Bangladesh. A new high performance liquid chromatography (HPLC) equipped with a UV detector method was developed for the identification of the phenolic acids and flavonoids. A total of five different phenolic acids were identified, with the most abundant being caffeic acid, benzoic acid, gallic acid, followed by chlorogenic acid and trans-cinnamic acid. The flavonoids, kaempferol, and catechin were most abundant, followed by myricetin and naringenin. The mean moisture content, total sugar content, and color characteristics of the honey samples were 18.36 ± 0.95%, 67.40 ± 5.63 g/100 g, and 129.27 ± 34.66 mm Pfund, respectively. The mean total phenolic acids, total flavonoid content, and proline content were 199.20 ± 135.23, 46.73 ± 34.16, and 556.40 ± 376.86 mg/kg, respectively, while the mean FRAP values and DPPH radical scavenging activity were 327.30 ± 231.87 μM Fe (II)/100 g and 36.95 ± 20.53%, respectively. Among the different types of honey, kalijira exhibited the highest phenolics and antioxidant properties. Overall, our study confirms that all the investigated honey samples are good sources of phenolic acids and flavonoids with good antioxidant properties.

Herbaspirillum seropedicae rfbB and rfbC genes are required for maize colonization.

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Balsanelli, Eduardo; Serrato, Rodrigo V; de Baura, Valter A; Sassaki, Guilherme; Yates, Marshall G; Rigo, Liu Un; Pedrosa, Fábio O; de Souza, Emanuel M; Monteiro, Rose A

2010-08-01

In this study we disrupted two Herbaspirillum seropedicae genes, rfbB and rfbC, responsible for rhamnose biosynthesis and its incoporation into LPS. GC-MS analysis of the H. seropedicae wild-type strain LPS oligosaccharide chain showed that rhamnose, glucose and N-acetyl glucosamine are the predominant monosaccharides, whereas rhamnose and N-acetyl glucosamine were not found in the rfbB and rfbC strains. The electrophoretic pattern of the mutants LPS was drastically altered when compared with the wild type. Knockout of rfbB or rfbC increased the sensitivity towards SDS, polymyxin B sulfate and salicylic acid. The mutants attachment capacity to maize root surface plantlets was 100-fold lower than the wild type. Interestingly, the wild-type capacity to attach to maize roots was reduced to a level similar to that of the mutants when the assay was performed in the presence of isolated wild-type LPS, glucosamine or N-acetyl glucosamine. The mutant strains were also significantly less efficient in endophytic colonization of maize. Expression analysis indicated that the rfbB gene is upregulated by naringenin, apigenin and CaCl(2). Together, the results suggest that intact LPS is required for H. seropedicae attachment to maize root and internal colonization of plant tissues. © 2010 Society for Applied Microbiology and Blackwell Publishing Ltd.

An in vitro transport model for rapid screening and predicting the permeability of candidate compounds at blood-brain barrier.

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Yang, Zhi-Hong; Sun, Xiao; Mei, Chao; Sun, Xiao-Bo; Liu, Xiao-Dong; Chang, Qi

2011-12-01

The aim of this study was to design and develop a simple in vitro blood-brain barrier (BBB) permeation model for elementarily and rapidly predicting the permeability of candidate compounds at BBB and further evaluating whether P-glycoprotein (P-gp) affects them across BBB. The model was mainly composed of cultured rat brain microvascular endothelial cells (rBMECs), glass contraption, and micropore membrane. First, we evaluated the model by morphological observation. Second, the restriction effects of paracellular transport were verified by measuring marker probes transport, and monitoring transendothelial electrical resistance (TEER) and leakage. Finally, protein expression and activity of P-gp were confirmed by carrying out Western blot analysis and polarized transport of rhodamine-123 (Rho123) in rBMECs. The rBMECs retained both endothelial cells and BBB features. The rBMECs model reproducibly attained approximately 130 Ω cm² on the steady-state TEER value, and displayed a barrier function to marker probes transport by decreasing the permeability. Protein band of 170 kDa manifested the existence of P-gp in the rBMECs, and the findings of cyclosporin A-sensitive decrease of Rho123 efflux confirmed the presence of P-gp activity. A simple, rapid, and convenient in vitro BBB permeation model was successfully established and applied to evaluate the BBB transport profiles of three natural flavonoids: quercetin, naringenin, and rutin.

Antioxidant Profile of Trifolium pratense L.

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Heidy Schwartsova

2012-09-01

Full Text Available In order to examine the antioxidant properties of five different extracts of Trifolium pratense L. (Leguminosae leaves, various assays which measure free radical scavenging ability were carried out: 1,1-diphenyl-2-picrylhydrazyl, hydroxyl, superoxide anion and nitric oxide radical scavenger capacity tests and lipid peroxidation assay. In all of the tests, only the H₂O and (to some extent the EtOAc extracts showed a potent antioxidant effect compared with BHT and BHA, well-known synthetic antioxidants. In addition, in vivo experiments were conducted with antioxidant systems (activities of GSHPx, GSHR, Px, CAT, XOD, GSH content and intensity of LPx in liver homogenate and blood of mice after their treatment with extracts of T. pratense leaves, or in combination with CCl₄. Besides, in the extracts examined the total phenolic and flavonoid amounts were also determined, together with presence of the selected flavonoids: quercetin, luteolin, apigenin, naringenin and kaempferol, which were studied using a HPLC-DAD technique. HPLC-DAD analysis showed a noticeable content of natural products according to which the examined Trifolium pratense species could well be regarded as a promising new source of bioactive natural compounds, which can be used both as a food supplement and a remedy.

Micropropagation of Cyclopia genistoides, an endemic South African plant of economic importance.

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Kokotkiewicz, Adam; Luczkiewicz, Maria; Hering, Anna; Ochocka, Renata; Gorynski, Krzysztof; Bucinski, Adam; Sowinski, Pawel

2012-01-01

An efficient micropropagation protocol of Cyclopia genistoides (L.) Vent., an indigenous South African shrub of economic importance, was established. In vitro shoot cultures were obtained from shoot tip fragments of sterile seedlings cultured on solid Schenk and Hildebrandt (SH) medium supplemented with 9.84 microM 6-(gamma,gamma-dimethylallylamino)purine (2iP) and 1.0 microM thidiazuron (TDZ). Maximum shoot multiplication rate [(8.2 +/- 1.3) microshoots/explant)] was observed on this medium composition. Prior to rooting, the multiplied shoots were elongated for 60 days (two 30-days passages) on SH medium with one-half sucrose concentration, supplemented with 4.92 microM indole-3-butyric acid (IBA). The rooting of explants was only possible in the case of the elongated shoots. The highest root induction rate (54.8%) was achieved on solid SH medium with one-half sucrose and one-half potassium nitrate and ammonium nitrate concentration, respectively, supplemented with 28.54 microM indole-3-acetic acid (IAA) and 260.25 microM citric acid. The plantlets were acclimatized for 30 days in the glasshouse, with the use of peat/gravel/perlite substrate (1:1:1). The highest acclimatization rate (80%) was obtained for explants rooted with the use of IAA-supplemented medium. The phytochemical profile of the regenerated plants was similar to that of the reference intact plant material. HPLC analyses showed that C. genistoides plantlets obtained by the micropropagation procedure kept the ability to produce xanthones (mangiferin and isomangiferin) and the flavanone hesperidin, characteristic of wild-growing shrubs.

Simultaneous HPLC determination of flavonoids and phenolic acids profile in Pêra-Rio orange juice.

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Mesquita, E; Monteiro, M

2018-04-01

The aim of this study was to develop and validate an HPLC-DAD method to evaluate the phenolic compounds profile of organic and conventional Pêra-Rio orange juice. The proposed method was validated for 10 flavonoids and 6 phenolic acids. A wide linear range (0.01-223.4μg·g -1 ), good accuracy (79.5-129.2%) and precision (CV≤3.8%), low limits of detection (1-22ng·g -1 ) and quantification (0.7-7.4μg), and overall ruggedness were attained. Good recovery was achieved for all phenolic compounds after extraction and cleanup. The method was applied to organic and conventional Pêra-Rio orange juices from beginning, middle and end of the 2016 harvest. Flavones rutin, nobiletin and tangeretin, and flavanones hesperidin, narirutin and eriocitrin were identified and quantified in all organic and conventional juices. Identity was confirmed by mass spectrometry. Nineteen non-identified phenolic compounds were quantified based on DAD spectra characteristic of the chemical class: 7 cinnamic acid derivatives, 6 flavanones and 6 flavones. The phenolic compounds profile of Pêra-Rio orange juices changed during the harvest; levels increased in organic orange juices, and decreased or were about the same in conventional orange juices. Phenolic compounds levels were higher in organic (0.5-1143.7mg·100g -1 ) than in conventional orange juices (0.5-689.7mg·100g -1 ). PCA differentiated organic from conventional FS and NFC juices, and conventional FCOJ from conventional FS and NFC juices, thus differentiating cultivation and processing. Copyright © 2017. Published by Elsevier Ltd.

Management of Varicose Veins and Chronic Venous Insufficiency in a Comparative Registry with Nine Venoactive Products in Comparison with Stockings.

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Belcaro, G; Dugall, M; Luzzi, R; Corsi, M; Ledda, A; Ricci, A; Pellegrini, L; Cesarone, M R; Hosoi, M; Errichi, B M; Cornelli, U; Cotellese, R; Agus, G; Feragalli, B

2017-09-01

The aim of this registry study was to compare products used to control symptoms of CVI. Endpoints of the study were microcirculation, effects on volume changes, and symptoms (analogue scale). Pycnogenol, venoruton, troxerutin, the complex diosmin-hesperidin, Antistax, Mirtoselect (bilberry), escin, and the combination Venoruton-Pycnogenol (VE-PY) were compared with compressions. No safety or tolerability problems were observed. At inclusion, measurements in the groups were comparable: 1,051 patients completed the registry. Best performers : Venoruton, Pycnogenol, and the combination VE-PY produced the best effects on skin flux. These products and the combination VE-PY better improved PO 2 and PCO 2 . The edema score was decreased more effectively with the combination and with Pycnogenol. Venoruton; Antistax also had good results. Considering volumetry, the best performers were the combination PY-VE and the two single products Venoruton and Pycnogenol. Antistax results for edema were also good. The best improvement in symptoms score were obtained with Pycnogenol and compression. A larger decrease in oxidative stress was observed with Pycnogenol, Venoruton, and with the VE-PY combination. Good effects of Antistax were also observed. Parestesias were lower with Pycnogenol and with Antistax. Considering the need for interventions, the best performers were Pycnogenol, VE-PY, and compression. The efficacy of Pycnogenol and the combination are competitive with stockings that do not have the same tolerability in warmer climates. A larger and more prolonged evaluation is suggested to evaluate cost-efficacy (and non-interference with drugs) of these products in the management of CVI. The registry is in progress; other products are in evaluation.

Sweetness and bitterness taste of meals per se does not mediate gastric emptying in humans.

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Little, Tanya J; Gupta, Nili; Case, R Maynard; Thompson, David G; McLaughlin, John T

2009-09-01

In cell line and animal models, sweet and bitter tastants induce secretion of signaling peptides (e.g., glucagon-like peptide-1 and cholecystokinin) and slow gastric emptying (GE). Whether human GE and appetite responses are regulated by the sweetness or bitterness per se of ingested food is, however, unknown. We aimed to determine whether intragastric infusion of "equisweet" (Study A) or "equibitter" (Study B) solutions slow GE to the same extent, and whether a glucose solution made sweeter by the addition of saccharin will slow GE more potently than glucose alone. Healthy nonobese subjects were studied in a single-blind, randomized fashion. Subjects received 500-ml intragastric infusions of predetermined equisweet solutions of glucose (560 mosmol/kgH(2)O), fructose (290 mosmol/kgH(2)O), aspartame (200 mg), and saccharin (50 mg); twice as sweet glucose + saccharin, water (volumetric control) (Study A); or equibitter solutions of quinine (0.198 mM), naringin (1 mM), or water (Study B). GE was evaluated using a [(13)C]acetate breath test, and hunger and fullness were scored using visual analog scales. In Study A, equisweet solutions did not empty similarly. Fructose, aspartame, and saccharin did not slow GE compared with water, but glucose did (P solution (P > 0.05, compared with glucose alone). In Study B, neither bitter tastant slowed GE compared with water. None of the solutions modulated perceptions of hunger or fullness. We conclude that, in humans, the presence of sweetness and bitterness taste per se in ingested solutions does not appear to signal to influence GE or appetite perceptions.

Designing Second Generation Anti-Alzheimer Compounds as Inhibitors of Human Acetylcholinesterase: Computational Screening of Synthetic Molecules and Dietary Phytochemicals.

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Hafsa Amat-Ur-Rasool

Full Text Available Alzheimer's disease (AD, a big cause of memory loss, is a progressive neurodegenerative disorder. The disease leads to irreversible loss of neurons that result in reduced level of acetylcholine neurotransmitter (ACh. The reduction of ACh level impairs brain functioning. One aspect of AD therapy is to maintain ACh level up to a safe limit, by blocking acetylcholinesterase (AChE, an enzyme that is naturally responsible for its degradation. This research presents an in-silico screening and designing of hAChE inhibitors as potential anti-Alzheimer drugs. Molecular docking results of the database retrieved (synthetic chemicals and dietary phytochemicals and self-drawn ligands were compared with Food and Drug Administration (FDA approved drugs against AD as controls. Furthermore, computational ADME studies were performed on the hits to assess their safety. Human AChE was found to be most approptiate target site as compared to commonly used Torpedo AChE. Among the tested dietry phytochemicals, berberastine, berberine, yohimbine, sanguinarine, elemol and naringenin are the worth mentioning phytochemicals as potential anti-Alzheimer drugs The synthetic leads were mostly dual binding site inhibitors with two binding subunits linked by a carbon chain i.e. second generation AD drugs. Fifteen new heterodimers were designed that were computationally more efficient inhibitors than previously reported compounds. Using computational methods, compounds present in online chemical databases can be screened to design more efficient and safer drugs against cognitive symptoms of AD.

Plant-derived health: the effects of turmeric and curcuminoids.

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Bengmark, S; Mesa, M D; Gil, A

2009-01-01

Plants contain numerous polyphenols, which have been shown to reduce inflammation and hereby to increase resistance to disease. Examples of such polyphenols are isothiocyanates in cabbage and broccoli, epigallocatechin in green tee, capsaicin in chili peppers, chalones, rutin and naringenin in apples, resveratrol in red wine and fresh peanuts and curcumin/curcuminoids in turmeric. Most diseases are maintained by a sustained discreet but obvious increased systemic inflammation. Many studies suggest that the effect of treatment can be improved by a combination of restriction in intake of proinflammatory molecules such as advanced glycation end products (AGE), advanced lipoperoxidation end products (ALE), and rich supply of antiinflammatory molecules such as plant polyphenols. To the polyphenols with a bulk of experimental documentation belong the curcuminoid family and especially its main ingredient, curcumin. This review summarizes the present knowledge about these turmericderived ingredients, which have proven to be strong antioxidants and inhibitors of cyclooxigenase-2 (COX-2), lipoxygenase (LOX) and nuclear factor kappa B (NF-kappaB) but also AGE. A plethora of clinical effects are reported in various experimental diseases, but clinical studies in humans are few. It is suggested that supply of polyphenols and particularly curcuminoids might be value as complement to pharmaceutical treatment, but also prebiotic treatment, in conditions proven to be rather therapy-resistant such as Crohn's, long-stayed patients in intensive care units, but also in conditions such as cancer, liver cirrhosis, chronic renal disease, chronic obstructive lung disease, diabetes and Alzheimer's disease.

Molecular displacement of warfarin from human serum albumin by flavonoid aglycones

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Poór, Miklós; Li, Yin; Kunsági-Máté, Sándor; Petrik, József; Vladimir-Knežević, Sanda; Kőszegi, Tamás

2013-01-01

The well-known 4-hydroxycoumarin derivative warfarin is a widespread anticoagulant drug. Besides its strong albumin binding property warfarin has a narrow therapeutic window. Therefore, a few percent of displacement from albumin can result in serious biological consequences. The flavonoid molecular group also shows very strong plasma albumin binding characteristics occupying the same binding site. It is plausible to hypothesize that flavonoid aglycones may be able to displace warfarin from human serum albumin (HSA). In our study the competing activities of different flavone (acacetin, apigenin, chrysin, luteolin), flavonol (galangin, quercetin) and flavanone (hesperetin, naringenin) aglycones were investigated using fluorescence spectroscopy. Our results represent that flavonoids are able to displace warfarin from the surface of HSA. On the other hand, when comparing flavone or flavonol groups to flavanones the latter group seems to be much weaker competitor. These observations were also supported by calculation of stability constants. Our investigations strongly suggest that we should reckon with the described molecular displacement. However, further in vivo studies are needed to support the findings of our model system. -- Highlights: • Various flavonoids are able to displace warfarin from human serum albumin. • Flavones and flavonols are much more effective competitors than flavanones. • Even 300 nM aglycone concentrations show the interaction with 3 μM warfarin. • Flavonoid pairs show quasi-additive desorbing property. • Flavones and flavonols are much stronger competitors than the examined drugs

Phytochemical compounds and antioxidant activities of the almond kernel (prunus dulcis mill.) from turkey

International Nuclear Information System (INIS)

Keser, S.; Demir, E.; Yilmaz, O.

2014-01-01

Almond belong to Rosaceae family and it is a rich source of nutrients because of phytochemicals including phenolic compounds, phytosterols, flavonoids, phenolic acids, vitamins and fatty acids. In this study, we determined antioxidant activities and phenolic, flavonoid, phytosterol, lipid soluble vitamin and fatty acid contents of almond kernel extract. Antioxidant activities of almond extract was investigated by DPPH, ABTS •+ , OH radical scavenging, metal chelating activity and determination of lipid peroxidation levels (TBARS). Almond extract scavenged 89.50% of the ABTS radical, 66.77% of the hydroxyl radical, and 87.30% of the DPPH radical. This extract was shown 72.05% of the metal chelating activity. Kaempferol (223.54 μg/g), naringenin (5.01 micro g/g), vanillic acid (110.89 micro g/g), caffeic acid (65.72 micro g/g) and ferulic acid (16.49 micro g/g) were determined in the almond extract. The major fatty acids were oleic acid (76.23%) and linoleic acid (15.43%) in almond extract. d-tocopherol (3.05 mg/kg), a-tocopherol (104.40 mg/kg), and vitamin K (38.25 mg/kg) were determined in the almond extract. These results indicate that almond extract is a good natural source of fatty acids, lipid soluble vitamins, phytosterols, flavonoid, phenolic compounds. In addition, these findings are important for the nutrition sciences, because fatty acids, lipid soluble vitamins, phytosterols, flavonoid, phenolic compounds and antiradical properties, in particular, seem to have considerable effect on health. (author)

AgFNS overexpression increase apigenin and decrease anthocyanins in petioles of transgenic celery.

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Tan, Guo-Fei; Ma, Jing; Zhang, Xin-Yue; Xu, Zhi-Sheng; Xiong, Ai-Sheng

2017-10-01

Apigenin and anthocyanin biosyntheses share common precursors in plants. Flavone synthase (FNS) converts naringenin into apigenin in higher plants. Celery is an important edible and medical vegetable crop that contains apigenin in its tissues. However, the effect of high AgFNS gene expression on the apigenin and anthocyanins contents of purple celery remains to be elucidated. In this study, the AgFNS gene was cloned from purple celery ('Nanxuan liuhe purple celery') and overexpressed in this purple celery to determine its influence on anthocyanins and apigenin contents. Results showed that the AgFNS gene was 1068bp, which encodes 355 amino acid residues. Evolution analysis showed that the AgFNS protein belongs to the FSN I type. In AgFNS transgenic celery, the anthocyanins content in petioles was lower than that wild-type celery plants. Apigenin content increased in the petioles of AgFNS transgenic celery. The transcript levels of the AgPAL, AgC4H, AgCHS, and AgCHI genes were up-regulated, whereas those of the AgF3H, AgF3'H, AgDFR, AgANS, and Ag3GT genes were down-regulated in the petioles of AgFNS transgenic plants compared with wild-type celery plants. This work provides basic knowledge about the function of the AgFNS gene in the anthocyanin and apigenin biosyntheses of celery. Copyright © 2017 Elsevier B.V. All rights reserved.

Extract of grapefruit-seed reduces acute pancreatitis induced by ischemia/reperfusion in rats: possible implication of tissue antioxidants.

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Dembinski, A; Warzecha, Z; Konturek, S J; Ceranowicz, P; Dembinski, M; Pawlik, W W; Kusnierz-Cabala, B; Naskalski, J W

2004-12-01

Grapefruit seed extract (GSE) has been shown to exert antibacterial, antifungal and antioxidant activity possibly due to the presence of naringenin, the flavonoid with cytoprotective action on the gastric mucosa. No study so far has been undertaken to determine whether this GSE is also capable of preventing acute pancreatic damage induced by ischemia/reperfusion (I/R), which is known to result from reduction of anti-oxidative capability of pancreatic tissue, and whether its possible preventive effect involves an antioxidative action of this biocomponent. In this study carried out on rats with acute hemorrhagic pancreatitis induced by 30 min partial pancreatic ischemia followed by 6 h of reperfusion, the GSE or vehicle (vegetable glycerin) was applied intragastrically in gradually increasing amounts (50-500 microl) 30 min before I/R. Pretreatment with GSE decreased the extent of pancreatitis with maximal protective effect of GSE at the dose 250 microl. GSE reduced the pancreatitis-evoked increase in serum lipase and poly-C specific ribonuclease activity, and attenuated the marked fall in pancreatic blood flow and pancreatic DNA synthesis. GSE administered alone increased significantly pancreatic tissue content of lipid peroxidation products, malondialdehyde and 4-hydroxyalkens, and when administered before I/R, GSE reduced the pancreatitis-induced lipid peroxidation. We conclude that GSE exerts protective activity against I/R-induced pancreatitis probably due to the activation of antioxidative mechanisms in the pancreas and the improvement of pancreatic blood flow.

Designing Second Generation Anti-Alzheimer Compounds as Inhibitors of Human Acetylcholinesterase: Computational Screening of Synthetic Molecules and Dietary Phytochemicals.

Science.gov (United States)

Amat-Ur-Rasool, Hafsa; Ahmed, Mehboob

2015-01-01

Alzheimer's disease (AD), a big cause of memory loss, is a progressive neurodegenerative disorder. The disease leads to irreversible loss of neurons that result in reduced level of acetylcholine neurotransmitter (ACh). The reduction of ACh level impairs brain functioning. One aspect of AD therapy is to maintain ACh level up to a safe limit, by blocking acetylcholinesterase (AChE), an enzyme that is naturally responsible for its degradation. This research presents an in-silico screening and designing of hAChE inhibitors as potential anti-Alzheimer drugs. Molecular docking results of the database retrieved (synthetic chemicals and dietary phytochemicals) and self-drawn ligands were compared with Food and Drug Administration (FDA) approved drugs against AD as controls. Furthermore, computational ADME studies were performed on the hits to assess their safety. Human AChE was found to be most approptiate target site as compared to commonly used Torpedo AChE. Among the tested dietry phytochemicals, berberastine, berberine, yohimbine, sanguinarine, elemol and naringenin are the worth mentioning phytochemicals as potential anti-Alzheimer drugs The synthetic leads were mostly dual binding site inhibitors with two binding subunits linked by a carbon chain i.e. second generation AD drugs. Fifteen new heterodimers were designed that were computationally more efficient inhibitors than previously reported compounds. Using computational methods, compounds present in online chemical databases can be screened to design more efficient and safer drugs against cognitive symptoms of AD.

¹H-NMR simultaneous identification of health-relevant compounds in propolis extracts.

Science.gov (United States)

Bertelli, Davide; Papotti, Giulia; Bortolotti, Laura; Marcazzan, Gian Luigi; Plessi, Maria

2012-01-01

Propolis is a resinous substance collected by bees from exudates of different plants that is rich in well-known health-relevant phenolic compounds such as flavonoids and phenolic acids. Propolis extracts are very complex matrices difficult to study. Different analytical methods are usable to analyse propolis extracts and to obtain chemical fingerprint but to our knowledge NMR has not previously been used for this purpose. This study aims to demonstrate that it is possible to use ¹H-NMR for the simultaneous recognition of phenolic compounds in complex matrices, such as propolis extracts, using appropriate tools for spectra pre-treatment and analysis. In this work 12 typical phenolic propolis compounds (apigenin, chrysin, galangin, kaempferol, quercetin, naringenin, pinocembrin, pinostrobin, caffeic acid, cinnamic acid, p-coumaric acid and ferulic acid) were considered as reference compounds and their presence in samples was verified by HPLC-MS. A simple ¹H-NMR sequence was used to obtain spectra of samples. Spectra were pre-treated by using an appropriate tool for spectra alignment and analysed by using software for the study of spectra originated from complex matrices. Sixty-five propolis samples were used to test the proposed identification procedure. Ten out of 12 considered compounds were identified as statistically significant in most of the samples. This work suggests that it is possible to efficiently use ¹H-NMR, coupled with appropriate spectral analytical tools, for the simultaneous detection of phenolic compounds in complex matrices. Copyright © 2011 John Wiley & Sons, Ltd.

Phenolic tyrosinase inhibitors from the stems of Cudrania cochinchinensis.

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Zheng, Zong-Ping; Zhu, Qin; Fan, Chun-Lin; Tan, Hui-Yuan; Wang, Mingfu

2011-05-01

The phytochemcal profiles of Cudrania cochinchinensis leaf, twig, stem and root were compared by HPLC analysis. It was found that C. cochinchinensis stem extract contained some unknown natural products with potential tyrosinase inhibitory activities. Therefore, the chemical constitutes in extract (95% ethanol) of C. cochinchinensis stem were further investigated in this study. A new racemic mixture, (±)2,3-cis-dihydromorin, and fifteen known phenolic compounds, dihydrokaempferol 7-O-β-d-qlucopyranoside, skimmin, quercetin-7-O-β-d-glucoside, 2,3-dihydroquercetin 7-O-β-d-glucoside, kaempferol-7-O-β-glucopyranoside, quercetin-3,7-di-O-β-d-glucoside, morin-7-O-β-d-glucoside, 1,3,5,8-tetrahydroxyxanthen-9-one, 2,3-trans-dihydromorin, aromadendrin, oxyresveratrol, genistin, protocatechuic acid, kaempferol 3,7-di-O-β-glucopyranoside, and naringenin were isolated. Spectral techniques (MS, (1)H NMR and (13)C NMR) were utilized for their structural identification and their inhibitory activities on mushroom tyrosinase were also evaluated. The results showed that tyrosinase inhibitory activities of (±)2,3-cis-dihydromorin (IC(50) = 31.1 μM), 2,3-trans-dihydromorin (IC(50) = 21.1 μM), and oxyresveratrol (IC(50) = 2.33 μM), were more potent than that of kojic acid (IC(50) = 50.8 μM), a well-known tyrosinase inhibitor, indicating that Cudrania cochinchinensis stem will be a great potential agent for the development of effective natural tyrosinase inhibitors.

Temperature-dependent release of volatile organic compounds of eucalypts by direct analysis in real time (DART) mass spectrometry.

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Maleknia, Simin D; Vail, Teresa M; Cody, Robert B; Sparkman, David O; Bell, Tina L; Adams, Mark A

2009-08-01

A method is described for the rapid identification of biogenic, volatile organic compounds (VOCs) emitted by plants, including the analysis of the temperature dependence of those emissions. Direct analysis in real time (DART) enabled ionization of VOCs from stem and leaf of several eucalyptus species including E. cinerea, E. citriodora, E. nicholii and E. sideroxylon. Plant tissues were placed directly in the gap between the DART ionization source skimmer and the capillary inlet of the time-of-flight (TOF) mass spectrometer. Temperature-dependent emission of VOCs was achieved by adjusting the temperature of the helium gas into the DART ionization source at 50, 100, 200 and 300 degrees C, which enabled direct evaporation of compounds, up to the onset of pyrolysis of plant fibres (i.e. cellulose and lignin). Accurate mass measurements facilitated by TOF mass spectrometry provided elemental compositions for the VOCs. A wide range of compounds was detected from simple organic compounds (i.e. methanol and acetone) to a series of monoterpenes (i.e. pinene, camphene, cymene, eucalyptol) common to many plant species, as well as several less abundant sesquiterpenes and flavonoids (i.e. naringenin, spathulenol, eucalyptin) with antioxidant and antimicrobial properties. The leaf and stem tissues for all four eucalypt species showed similar compounds. The relative abundances of methanol and ethanol were greater in stem wood than in leaf tissue suggesting that DART could be used to investigate the tissue-specific transport and emissions of VOCs. Copyright (c) 2009 John Wiley & Sons, Ltd.

Profile of plasma and urine metabolites after the intake of almond [Prunus dulcis (Mill.) D.A. Webb] polyphenols in humans.

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Urpi-Sarda, Mireia; Garrido, Ignacio; Monagas, María; Gómez-Cordovés, Carmen; Medina-Remón, Alexander; Andres-Lacueva, Cristina; Bartolomé, Begoña

2009-11-11

Nut skins are considered to be a rich source of polyphenols and may be partially responsible for the numerous health effects associated with nut consumption. However, more bioavailability studies of nut skin polyphenols are needed to understand the health effects derived from nut consumption. The aim of the present study was to determine the profiles of both phase II and microbial-derived phenolic metabolites in plasma and urine samples before and after the intake of almond skin polyphenols by healthy human subjects (n = 2). Glucuronide, O-methyl glucuronide, sulfate, and O-methyl sulfate derivatives of (epi)catechin, as well as the glucuronide conjugates of naringenin and glucuronide and sulfate conjugates of isorhamnetin, were detected in plasma and urine samples after consumption of almond skin polyphenols. The main microbial-derived metabolites of flavanols, such as 5-(dihydroxyphenyl)-gamma-valerolactone and 5-(hydroxymethoxyphenyl)-gamma-valerolactone, were also detected in their glucuronide and sulfate forms. In addition, numerous metabolites derived from further microbial degradation of hydroxyphenylvalerolactones, including hydroxyphenylpropionic, hydroxyphenylacetic, hydroxycinnamic, hydroxybenzoic, and hydroxyhippuric acids, registered major changes in urine after the consumption of almond skin polyphenols. The urinary excretion of these microbial metabolites was estimated to account for a larger proportion of the total polyphenol ingested than phase II metabolites of (epi)catechin, indicating the important role of intestinal bacteria in the metabolism of highly polymerized almond skin polyphenols. To the authors' knowledge this study constitutes the most complete report of the absorption of almond skin polyphenols in humans.

Simultaneous determination of five free and total flavonoids in rat plasma by ultra HPLC-MS/MS and its application to a comparative pharmacokinetic study in normal and hyperlipidemic rats.

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Wang, Xiaofan; Zhao, Xu; Gu, Liqiang; Lv, Chunxiao; He, Bosai; Liu, Zhenzhen; Hou, Pengyi; Bi, Kaishun; Chen, Xiaohui

2014-03-15

A simple and rapid ultra-high performance liquid chromatography-tandem mass spectrometry (uHPLC-MS/MS) method has been developed for the simultaneous determination of five free flavonoids (amentoflavone, isorhamnetin, naringenin, kaempferol and quercetin) and their total (free and conjugated) forms, and to compare the pharmacokinetics of these active ingredients in normal and hyperlipidemic rats. The free and total forms of these flavonoids were extracted by liquid-liquid extraction with ethyl acetate. The conjugated flavonoids were deconjugated by the enzyme β-Glucuronidase and Sulfatase. Chromatographic separation was accomplished on a ZORBAX Eclipse XDB-C8 USP L7 column using gradient elution. Detection was performed on a 4000Q uHPLC-MS/MS system from AB Sciex using negative ion mode in the multiple reaction monitoring (MRM) mode. The lower limits of quantification were 2.0-5.0ng/mL for all the analytes. Intra-day and inter-day precision were less than 15% and accuracy ranged from -9.3% to 11.0%, and the mean extraction recoveries of analytes and internal standard (IS) from rat plasma were all more than 81.7%. The validated method was successfully applied to a comparative pharmacokinetic study of five free and total analytes in rat plasma. The results indicated that the absorption of five total flavonoids in hyperlipidemia group were significantly higher than those in normal group with similar concentration-time curves. Copyright © 2014 Elsevier B.V. All rights reserved.

Molecular and Biochemical Analysis of Chalcone Synthase from Freesia hybrid in flavonoid biosynthetic pathway.

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Wei Sun

Full Text Available Chalcone synthase (CHS catalyzes the first committed step in the flavonoid biosynthetic pathway. In this study, the cDNA (FhCHS1 encoding CHS from Freesia hybrida was successfully isolated and analyzed. Multiple sequence alignments showed that both the conserved CHS active site residues and CHS signature sequence were found in the deduced amino acid sequence of FhCHS1. Meanwhile, crystallographic analysis revealed that protein structure of FhCHS1 is highly similar to that of alfalfa CHS2, and the biochemical analysis results indicated that it has an enzymatic role in naringenin biosynthesis. Moreover, quantitative real-time PCR was performed to detect the transcript levels of FhCHS1 in flowers and different tissues, and patterns of FhCHS1 expression in flowers showed significant correlation to the accumulation patterns of anthocyanin during flower development. To further characterize the functionality of FhCHS1, its ectopic expression in Arabidopsis thaliana tt4 mutants and Petunia hybrida was performed. The results showed that overexpression of FhCHS1 in tt4 mutants fully restored the pigmentation phenotype of the seed coats, cotyledons and hypocotyls, while transgenic petunia expressing FhCHS1 showed flower color alteration from white to pink. In summary, these results suggest that FhCHS1 plays an essential role in the biosynthesis of flavonoid in Freesia hybrida and may be used to modify the components of flavonoids in other plants.

Sensory-guided decomposition of roasted cocoa nibs (Theobroma cacao) and structure determination of taste-active polyphenols.

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Stark, Timo; Bareuther, Sabine; Hofmann, Thomas

2005-06-29

Sequential application of solvent extraction, gel permeation chromatography, and RP-HPLC in combination with taste dilution analyses, followed by LC-MS and 1D/2D-NMR experiments and thiolytic degradation, revealed that, besides theobromine and caffeine, the flavan-3-ols epicatechin, catechin, procyanidin B-2, procyanidin B-5, procyanidin C-1, [epicatechin-(4beta-->8)](3)-epicatechin, and [epicatechin-(4beta-->8)](4)-epicatechin were among the key compounds contributing to the bitter taste as well as the astringent mouthfeel imparted upon consumption of roasted cocoa. In addition, a series of quercetin, naringenin, luteolin, and apigenin glycopyranosides as well as a family of not previously identified amino acid amides, namely, (+)-N-[4'-hydroxy-(E)-cinnamoyl]-L-aspartic acid, (+)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-aspartic acid, (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine, (+)-N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-L-aspartic acid, and (+)-N-(E)-cinnamoyl-L-aspartic acid, have been identified as key astringent compounds of roasted cocoa. Furthermore, (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-3-hydroxy-l-tyrosine (clovamide), (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-tyrosine (deoxyclovamide), and (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine, reported previously as antioxidants, have been found as contributors of cocoa's astringent taste. By means of the half-tongue test, the taste thresholds of flavan-3-ols and glycosides have been determined.

LC-DAD-MS (ESI+) analysis and antioxidant capacity of crocus sativus petal extracts.

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Termentzi, Aikaterini; Kokkalou, Eugene

2008-04-01

In this study, various fractions isolated from the petals of Crocus sativus were assessed at first for their phenolic content both qualitatively and quantitatively and secondly for their antioxidant activity. The phytochemical analysis was carried out by LC-DAD-MS (ESI (+)) whereas the antioxidant potential was evaluated by applying two methodologies, the DPPH. radical scavenging activity test and the Co(II)-induced luminol chemiluminescence procedure. According to data obtained from these antioxidant tests, the diethyl ether, ethyl acetate and aqueous fractions demonstrated the strongest antioxidant capacity. Interestingly, the major constituents identified in these fractions correspond to kaempferol, quercetin, naringenin and some flavanone and flavanol derivatives glycosylated and esterified with phenylpropanoic acids. In addition, the presence of some nitrogen-containing substances, as well as other phenolics and phenylpropanoic derivatives was also traced. The identification and structural elucidation of all substances isolated in this study was achieved by both comparing available literature data and by proposed fragmentation mechanisms based on evaluating the LC-DAD-MS (ESI (+)) experimental data. The quantitative analysis data obtained thus far have shown that Crocus sativus petals are a rich source of flavonoids. Such a fact suggests that the good antioxidant capacity detected in the various fractions of Crocus sativus petals could be attributed to the presence of flavonoids, since it is already known that these molecules exert antioxidant capability. The latter, along with the use of Crocus sativus in food and pharmaceutical industry is discussed.

Transcriptomics and metabolite analysis reveals the molecular mechanism of anthocyanin biosynthesis branch pathway in different Senecio cruentus cultivars

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Xuehua Jin

2016-09-01

Full Text Available The cyanidin (Cy, pelargonidin (Pg and delphinidin (Dp pathways are the three major branching anthocyanin biosynthesis pathways that regulate flavonoid metabolic flux and are responsible for red, orange and blue flower colors, respectively. Different species have evolved to develop multiple regulation mechanisms that form the branched pathways. In the current study, five Senecio cruentus cultivars with different colors were investigated. We found that the white and yellow cultivars do not accumulate anthocyanin and that the blue, pink and carmine cultivars mainly accumulate Dp, Pg and Cy in differing densities. Subsequent transcriptome analysis determined that there were 43 unigenes encoding anthocyanin biosynthesis genes in the blue cultivar. We also combined chemical and transcriptomic analyses to investigate the major metabolic pathways that are related to the observed differences in flower pigmentation in the series of S. cruentus. The results showed that mutations of the ScbHLH17 and ScCHI1/2 coding regions abolish anthocyanin formation in the white and the yellow cultivars; the competition of the ScF3’H1, ScF3’5’H and ScDFR1/2 genes for naringenin determines the differences in branching metabolic flux of the Cy, Dp and Pg pathways. Our findings provide new insights into the regulation of anthocyanin branching and also supplement gene resources (including ScF3’5’H, ScF3’H and ScDFRs for flower color modification of ornamentals.

Citrus Flavonoids as Regulators of Lipoprotein Metabolism and Atherosclerosis.

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Mulvihill, Erin E; Burke, Amy C; Huff, Murray W

2016-07-17

Citrus flavonoids are polyphenolic compounds with significant biological properties. This review summarizes recent advances in understanding the ability of citrus flavonoids to modulate lipid metabolism, other metabolic parameters related to the metabolic syndrome, and atherosclerosis. Citrus flavonoids, including naringenin, hesperitin, nobiletin, and tangeretin, have emerged as potential therapeutics for the treatment of metabolic dysregulation. Epidemiological studies reveal an association between the intake of citrus flavonoid-containing foods and a decreased incidence of cardiovascular disease. Studies in cell culture and animal models, as well as a limited number of clinical studies, reveal the lipid-lowering, insulin-sensitizing, antihypertensive, and anti-inflammatory properties of citrus flavonoids. In animal models, supplementation of rodent diets with citrus flavonoids prevents hepatic steatosis, dyslipidemia, and insulin resistance primarily through inhibition of hepatic fatty acid synthesis and increased fatty acid oxidation. Citrus flavonoids blunt the inflammatory response in metabolically important tissues including liver, adipose, kidney, and the aorta. The mechanisms underlying flavonoid-induced metabolic regulation have not been completely established, although several potential targets have been identified. In mouse models, citrus flavonoids show marked suppression of atherogenesis through improved metabolic parameters as well as through direct impact on the vessel wall. Recent studies support a role for citrus flavonoids in the treatment of dyslipidemia, insulin resistance, hepatic steatosis, obesity, and atherosclerosis. Larger human studies examining dose, bioavailability, efficacy, and safety are required to promote the development of these promising therapeutic agents.

Involvement of Smad3 pathway in atrial fibrosis induced by elevated hydrostatic pressure.

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Wei, Wei; Rao, Fang; Liu, Fangzhou; Xue, Yumei; Deng, Chunyu; Wang, Zhaoyu; Zhu, Jiening; Yang, Hui; Li, Xin; Zhang, Mengzhen; Fu, Yongheng; Zhu, Wensi; Shan, Zhixin; Wu, Shulin

2018-06-01

Hypertension is a main risk factor for atrial fibrillation, but the direct effects of hydrostatic pressure on the atrial fibrosis are still unknown. The present study investigated whether hydrostatic pressure is responsible for atrial fibrosis, and addressed a potential role of the Smad pathway in this pathology. Biochemical assays were used to study regulation and expression of fibrotic factors in spontaneously hypertensive rats (SHRs) and Wistar rats, and in cardiac fibroblasts (CFs) cultured under standard (0 mmHg) and elevated (20, 40 mmHg) hydrostatic pressure. Levels of atrial fibrosis and protein expression of fibrotic factors Col-1A1/-3A1, TGF-β1, and MMP-2 in SHRs' left atrial tissues were higher than those in Wistar rats. Exposure to elevated pressure was associated with the proliferation of CFs. The protein expression of Col-1A1/-3A1, TGF-β1, and MMP-2 in CFs was also up-regulated in a pressure-dependent manner. The proliferation of CFs and increased expressions of fibrotic markers induced by elevated hydrostatic pressure could be reversed by the Smad3 inhibitor naringenin. The activation of Smad3 pathway was also stimulated by elevated hydrostatic pressure. These results demonstrate that CF secretory function and proliferation can be up-regulated by exposure to elevated pressure, and that Smad3 may modulate CF activation induced by high hydrostatic pressure. © 2017 Wiley Periodicals, Inc.

Sechium edule (Jacq. Swartz, a New Cultivar with Antiproliferative Potential in a Human Cervical Cancer HeLa Cell Line

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Sandra Salazar-Aguilar

2017-07-01

Full Text Available The Sechium edule Perla Negra cultivar is a recently-obtained biological material whose progenitors are S. edule var. nigrum minor and S. edule var. amarus silvestrys, the latter of which has been reported to have antiproliferative activity against the HeLa P-388 and L-929 cancer cell lines. The present study aimed to determine if the methanolic extract of the fruit of the Perla Negra cultivar had the same biological activity. The methanolic extract was phytochemically characterized by thin layer chromatography (TLC and column chromatography (CC, identifying the terpenes and flavonoids. The compounds identified via high performance liquid chromatography (HPLC were Cucurbitacins B, D, E, and I for the terpene fractions, and Rutin, Phlorizidin, Myricetin, Quercetin, Naringenin, Phloretin, Apigenin, and Galangin for the flavonoid fractions. Biological activity was evaluated with different concentrations of the methanolic extract in the HeLa cell line and normal lymphocytes. The methanolic extract inhibited the proliferation of HeLa cells (IC50 1.85 µg·mL−1, but the lymphocytes were affected by the extract (IC50 30.04 µg·mL−1. Some fractions, and the pool of all of them, showed inhibition higher than 80% at a concentration of 2.11 µg·mL−1. Therefore, the biological effect shown by the methanolic extract of the Perla Negra has some specificity in inhibiting tumor cells and not normal cells; an unusual feature among molecules investigated as potential biomedical agents.

Sechium edule (Jacq.) Swartz, a New Cultivar with Antiproliferative Potential in a Human Cervical Cancer HeLa Cell Line.

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Salazar-Aguilar, Sandra; Ruiz-Posadas, Lucero Del Mar; Cadena-Iñiguez, Jorge; Soto-Hernández, Marcos; Santiago-Osorio, Edelmiro; Aguiñiga-Sánchez, Itzen; Rivera-Martínez, Ana Rocío; Aguirre-Medina, Juan Francisco

2017-07-25

The Sechium edule Perla Negra cultivar is a recently-obtained biological material whose progenitors are S. edule var. nigrum minor and S. edule var. amarus silvestrys, the latter of which has been reported to have antiproliferative activity against the HeLa P-388 and L-929 cancer cell lines. The present study aimed to determine if the methanolic extract of the fruit of the Perla Negra cultivar had the same biological activity. The methanolic extract was phytochemically characterized by thin layer chromatography (TLC) and column chromatography (CC), identifying the terpenes and flavonoids. The compounds identified via high performance liquid chromatography (HPLC) were Cucurbitacins B, D, E, and I for the terpene fractions, and Rutin, Phlorizidin, Myricetin, Quercetin, Naringenin, Phloretin, Apigenin, and Galangin for the flavonoid fractions). Biological activity was evaluated with different concentrations of the methanolic extract in the HeLa cell line and normal lymphocytes. The methanolic extract inhibited the proliferation of HeLa cells (IC 50 1.85 µg·mL -1 ), but the lymphocytes were affected by the extract (IC 50 30.04 µg·mL -1 ). Some fractions, and the pool of all of them, showed inhibition higher than 80% at a concentration of 2.11 µg·mL -1 . Therefore, the biological effect shown by the methanolic extract of the Perla Negra has some specificity in inhibiting tumor cells and not normal cells; an unusual feature among molecules investigated as potential biomedical agents.

Molecular displacement of warfarin from human serum albumin by flavonoid aglycones

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Poór, Miklós [Institute of Laboratory Medicine, University of Pécs, Pécs H-7624 (Hungary); Li, Yin; Kunsági-Máté, Sándor [Department of General and Physical Chemistry, University of Pécs, Pécs H-7624 (Hungary); János Szentágothai Research Center, H-7624 Pécs (Hungary); Petrik, József [Department of Medical Biochemistry and Hematology, Faculty of Pharmacy and Biochemistry, University of Zagreb, HR-10000 Zagreb (Croatia); Vladimir-Knežević, Sanda [Department of Pharmacognosy, Faculty of Pharmacy and Biochemistry, University of Zagreb, HR-10000 Zagreb (Croatia); Kőszegi, Tamás, E-mail: koszegit@freemail.hu [Institute of Laboratory Medicine, University of Pécs, Pécs H-7624 (Hungary)

2013-10-15

The well-known 4-hydroxycoumarin derivative warfarin is a widespread anticoagulant drug. Besides its strong albumin binding property warfarin has a narrow therapeutic window. Therefore, a few percent of displacement from albumin can result in serious biological consequences. The flavonoid molecular group also shows very strong plasma albumin binding characteristics occupying the same binding site. It is plausible to hypothesize that flavonoid aglycones may be able to displace warfarin from human serum albumin (HSA). In our study the competing activities of different flavone (acacetin, apigenin, chrysin, luteolin), flavonol (galangin, quercetin) and flavanone (hesperetin, naringenin) aglycones were investigated using fluorescence spectroscopy. Our results represent that flavonoids are able to displace warfarin from the surface of HSA. On the other hand, when comparing flavone or flavonol groups to flavanones the latter group seems to be much weaker competitor. These observations were also supported by calculation of stability constants. Our investigations strongly suggest that we should reckon with the described molecular displacement. However, further in vivo studies are needed to support the findings of our model system. -- Highlights: • Various flavonoids are able to displace warfarin from human serum albumin. • Flavones and flavonols are much more effective competitors than flavanones. • Even 300 nM aglycone concentrations show the interaction with 3 μM warfarin. • Flavonoid pairs show quasi-additive desorbing property. • Flavones and flavonols are much stronger competitors than the examined drugs.

Potentiation of ghrelin signaling attenuates cancer anorexia–cachexia and prolongs survival

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Fujitsuka, N; Asakawa, A; Uezono, Y; Minami, K; Yamaguchi, T; Niijima, A; Yada, T; Maejima, Y; Sedbazar, U; Sakai, T; Hattori, T; Kase, Y; Inui, A

2011-01-01

Cancer anorexia–cachexia syndrome is characterized by decreased food intake, weight loss, muscle tissue wasting and psychological distress, and this syndrome is a major source of increased morbidity and mortality in cancer patients. This study aimed to clarify the gut–brain peptides involved in the pathogenesis of the syndrome and determine effective treatment for cancer anorexia–cachexia. We show that both ghrelin insufficiency and resistance were observed in tumor-bearing rats. Corticotropin-releasing factor (CRF) decreased the plasma level of acyl ghrelin, and its receptor antagonist, α-helical CRF, increased food intake of these rats. The serotonin 2c receptor (5-HT2cR) antagonist SB242084 decreased hypothalamic CRF level and improved anorexia, gastrointestinal (GI) dysmotility and body weight loss. The ghrelin receptor antagonist (D-Lys3)-GHRP-6 worsened anorexia and hastened death in tumor-bearing rats. Ghrelin attenuated anorexia–cachexia in the short term, but failed to prolong survival, as did SB242084 administration. In addition, the herbal medicine rikkunshito improved anorexia, GI dysmotility, muscle wasting, and anxiety-related behavior and prolonged survival in animals and patients with cancer. The appetite-stimulating effect of rikkunshito was blocked by (D-Lys3)-GHRP-6. Active components of rikkunshito, hesperidin and atractylodin, potentiated ghrelin secretion and receptor signaling, respectively, and atractylodin prolonged survival in tumor-bearing rats. Our study demonstrates that the integrated mechanism underlying cancer anorexia–cachexia involves lowered ghrelin signaling due to excessive hypothalamic interactions of 5-HT with CRF through the 5-HT2cR. Potentiation of ghrelin receptor signaling may be an attractive treatment for anorexia, muscle wasting and prolong survival in patients with cancer anorexia–cachexia. PMID:22832525

Pull-out bond strength of a self-adhesive resin cement to NaOCl-treated root dentin: effect of antioxidizing agents

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Maryam Khoroushi

2014-05-01

Full Text Available Objectives This study evaluated the effect of three antioxidizing agents on pull-out bond strengths of dentin treated with sodium hypochlorite. Materials and Methods Root canals of 75 single-rooted human teeth were prepared. Fifteen teeth were irrigated with normal saline for a negative control group, and the remaining 60 teeth (groups 2 - 5 with 2.5% NaOCl. The teeth in group 2 served as a positive control. Prior to post cementation, the root canals in groups 3 - 5 were irrigated with three antioxidizing agents including 10% rosmarinic acid (RA, Baridge essence, 10% hesperidin (HPN, Sigma, and 10% sodium ascorbate hydrogel (SA, AppliChem. Seventy-five spreaders (#55, taper .02, Produits Dentaires S.A were coated with silica and silanized with the Rocatec system and ceramic bond. All the prepared spreaders were cemented with a self-adhesive resin cement (Bifix SE, Voco Gmbh in the prepared canals. After storage in distilled water (24 h/37℃, the spreaders were pulled out in a universal testing machine at a crosshead speed of 1.0 mm/min. Pull-out strength values were analyzed by one-way ANOVA and Tukey's HSD test (α = 0.05. Results There were significant differences between study groups (p = 0.016. The highest pull-out strength was related to the SA group. The lowest strength was obtained in the positive control group. Conclusions Irrigation with NaOCl during canal preparation decreased bond strength of resin cement to root dentin. Amongst the antioxidants tested, SA had superior results in reversing the diminishing effect of NaOCl irrigation on the bond strength to root dentin.

Kinetics of Hesperetin for Liver Fortification in gamma-Irradiated Mice

International Nuclear Information System (INIS)

Tawfik, S.S.

2011-01-01

Hesperetin (3',5,7-trihydroxy-4'-methoxyflavonone), the aglycone of the flavanone glycosides hesperidin, exerts pharmacological properties such as antioxidation, anti-inflammation, blood lipid and cholesterol lowering is effectively used as a supplemental agent in the treatment protocols of complementary settings. Four groups were prepared: Control group: received 0.5 ml normal saline for 7 days. Hesperetin group: Mice received 7 doses of hesperetin injections (100 mg/ kg body wt/ day). Irradiated group: Mice submitted to total body irradiation with 4 Gy gamma-rays. Protected group (Hesperetin plus irradiation): Mice received hesperetin for 7 days and then submitted to 4 Gy of gamma-rays. The mice were sacrificed at 24 h, 1 week and 2 weeks after the end of the experimental treatments. Irradiated mice exhibited significant hyperglycaemia and augmented hepatic glycogen after the first day and 1 week but significant hypoglycemia and reducing hepatic glycogen after 2 weeks. Also, they exhibited significant increased serum total cholesterol (TC) and triacylglycerols (TG) and decreased hepatic TC and TG after 1 and 2 weeks. This treatment also resulted in a significant dropped in hepatic glucokinase (GK), glucose-6-phosphatase (G6P) and phosphoenolpyruvate carboxykinase (PEPCK) activities after 1 and 2 weeks. Hesperetin injections modulated the serum glucose and hepatic glycogen, adjusted TC and TG in both serum and liver and ameliorated the lessening in hepatic GK, G6P and PEPCK. The attending results demonstrated that hesperetn treatment modulated the biochemical symptoms of radiation disorders in mice. In conclusion, administration of hesperetin may have a useful role in modulating oxidative stress induced by exposure to gamma-radiation by improving the natural antioxidant mechanism and fortification liver functions

KADAR DAN IDENTIFIKASI SENYAWA POLIFENOL PADA WINE TERBUAT DARI CAMPURAN BUAH EKSTRAK DELIMA DAN PISANG (THE IDENTIFICATION OF POLYPHENOL COMPOUNDS AND ITS CONTENT OF WINE DERIVED FROM MIXED FRUITS OF POMEGRANATE AND BANANA

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Sonya Titin Nge

2017-01-01

Full Text Available ABSTRACTThis research aimed at describing quality and identifies polyphenols of wine made from a mixture of banana and pomegranate fruits. The wines with four different ratios of pomegranate-banana fruits were made (pomegranate: banana: 75:25; 62,5:37,5; 50:50; and 0:100 (control. Ethanol concentrations and taste were used as quality criteria. The ethanol was measured using gas chromatography and the tastes were determined with organoleptic test. HPLC methods were used to measure the total polyphenols and identify their chemical identity. The results of this research was that the ethanol concentration (% varied between treatments (pomegranate: banana extract, %: 10,33 (75:25; 8,62 (62,5:37,5; 4,88 (50:50; and 9,44 (100: 0 and the organoleptic test by 30 panelist resulted in that the mixture of pomegranate:banana of 50:50 (% was prefered most. The result also showed that the total polyphenol varied from 3,902 to 4,897 mg/ml, in which the more the pomegranate extract added the more the total polyphenol present in the wine. Further, HPLC analysis of polyphenol for wine with different combined fruit extracts (75:25; 62,5:37,5; 50:50; and 0:100 resulted in the identification of 41, 42, and 42, and 22 peak respectively. Predominant types of polyphenols in pomegranate extract added wine are galloyl-hexoxide, ferulic acid, chlorogenic acid, gallic acid, caffeic acid, catechin, epicatechin, punicalagin α, β punicalagin, and elagic acid. On the otherhand few polyphenols were present dominantly or exclusively in banana extract added wine: naringenin, quercetin-deoxyhexose, and rutin.ABSTRAK Penelitian ini bertujuan mendeskripsikan kualitas dan mengidentifikasi polifenol yang terkandung di dalam wine yang dibuat dari campuran buah pisang dan delima. Wine dimaksudkan dibuat dalam 4 perlakuan berbeda berdasarkan % ekstrak buah delima: pisang, yakni berturut-turut dalam rasio: 75:25; 62,5:37,5; 50:50; dan 0:100 (kontrol. Konsentrasi etanol dan citarasa

[Review for treatment effect and signaling pathway regulation of kidney-tonifying traditional Chinese medicine on osteoporosis].

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Xiao, Ya-Ping; Zeng, Jie; Jiao, Lin-Na; Xu, Xiao-Yu

2018-01-01

The treatment effect and signaling pathway regulation effects of kidney-tonifying traditional Chinese medicine on osteoporosis have been widely studied, but there is no systematic summary currently. This review comprehensively collected and analyzed the traditional Chinese medicines on the treatment and signaling pathway regulation of osteoporosis in recent ten years, such as Epimedii Folium, Drynariae Rhizoma, Cnidii Fructus, Eucommiae Cortex, Psoraleae Fructus and Dipsaci Radix. Based on the existing findings, the following conclusions were obtained: ①kidney-tonifying traditional Chinese medicine treated osteoporosis mainly through BMP-Smads, Wnt/ β -catenin, MAPK, PI3K/AKT signaling pathway to promote osteoblast bone formation and through OPG/RANKL/ RANK, estrogen, CTSK signaling pathway to inhibit osteoclasts of bone resorption. Epimedii Folium, Drynariae Rhizoma, Cnidii Fructus and Psoraleae Fructus up-regulated the expression of key proteins and genes of BMP-Smads and Wnt/ β -catenin signaling pathways to promote bone formation. Epimedii Folium, Drynariae Rhizoma, Cnidii Fructus, Eucommiae Cortex, Psoraleae Fructus and Dipsaci Radix inhibited the bone resorption by mediating the OPG/RANKL/RANK signaling pathway. ②Kidney-tonifying traditional Chinese medicine prevented and treated osteoporosis through a variety of ways: icariin in Epimedii Folium, naringin in Drynariae Rhizoma, osthole in Cnidii Fructus and psoralen in Psoraleae Fructus can regulate BMP-Smads, Wnt/ β -catenin signaling pathway to promote bone formation, but also activate OPG/RANKL/RANK, CTSK and other signaling pathways to inhibit bone resorption. ③The crosstalk of the signaling pathways and the animal experiments of the traditional Chinese medicine on the prevention and treatment of osteoporosis as well as their multi-target mechanism and comprehensive regulation need further clarification. Copyright© by the Chinese Pharmaceutical Association.

Metabolism of rutin and poncirin by human intestinal microbiota and cloning of their metabolizing α-L-rhamnosidase from Bifidobacterium dentium.

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Bang, Seo-Hyeon; Hyun, Yang-Jin; Shim, Juwon; Hong, Sung-Woon; Kim, Dong-Hyun

2015-01-01

To understand the metabolism of flavonoid rhamnoglycosides by human intestinal microbiota, we measured the metabolic activity of rutin and poncirin (distributed in many functional foods and herbal medicine) by 100 human stool specimens. The average α-Lrhamnosidase activities on the p-nitrophenyl-α-L-rhamnopyranoside, rutin, and poncirin subtrates were 0.10 ± 0.07, 0.25 ± 0.08, and 0.15 ± 0.09 pmol/min/mg, respectively. To investigate the enzymatic properties, α-L-rhamnosidase-producing bacteria were isolated from the specimens, and the α-L-rhamnosidase gene was cloned from a selected organism, Bifidobacterium dentium, and expressed in E. coli. The cloned α-L-rhamnosidase gene contained a 2,673 bp sequcence encoding 890 amino acid residues. The cloned gene was expressed using the pET 26b(+) vector in E. coli BL21, and the expressed enzyme was purified using Ni(2+)-NTA and Q-HP column chromatography. The specific activity of the purified α-L-rhamnosidase was 23.3 μmol/min/mg. Of the tested natural product constituents, the cloned α-L-rhamnosidase hydrolyzed rutin most potently, followed by poncirin, naringin, and ginsenoside Re. However, it was unable to hydrolyze quercitrin. This is the first report describing the cloning, expression, and characterization of α-L-rhamnosidase, a flavonoid rhamnoglycosidemetabolizing enzyme, from bifidobacteria. Based on these findings, the α-L-rhamnosidase of intestinal bacteria such as B. dentium seem to be more effective in hydrolyzing (1-->6) bonds than (1-->2) bonds of rhamnoglycosides, and may play an important role in the metabolism and pharmacological effect of rhamnoglycosides.

Ripening-Dependent Changes in Antioxidants, Color Attributes, and Antioxidant Activity of Seven Tomato (Solanum lycopersicum L. Cultivars

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Shiva Ram Bhandari

2016-01-01

Full Text Available To evaluate the ripening-dependent changes in phytonutrients, seven commercial cultivars (two general and five cherry of tomatoes were cultivated under greenhouse conditions. Fruits were harvested at breaker, turning, pink, light red, and red stages of each cultivar, and antioxidant contents, color attributes, and antioxidant activities were measured. During ripening process, lycopene content increased from the breaker to red stage, while lutein displayed the reverse accumulation pattern, with higher values during the breaker stage. In contrast, β-carotene showed the highest levels of synthesis in pink and light red stages. Furthermore, flavonoids (quercetin, rutin, naringenin, and luteolin also showed similar ripening-dependent changes, with higher quantities in pink and light red stages. Ascorbic acid showed continuously increasing patterns throughout ripening until the red stage, while the accumulation of total phenolics was cultivar-dependent. These results indicate that each antioxidant compound has a unique pattern of accumulation and degradation during the ripening process. “Unicon” exhibited highest total carotenoid (110.27 mg/100 g, total phenol (297.88 mg GAE/100 g and total flavonoid content (273.33 mg/100 g, and consequently highest antioxidant activity (2552.4 μmol TE/100 g compared to other cultivars. Throughout the ripening processes, total phenolics showed the highest correlation with antioxidant activity, followed by β-carotene and total flavonoids. In conclusion, ripening in tomatoes is accompanied by incremental increases in various antioxidant compounds to some extent, as well as by concomitant increases in antioxidant activity.

Assessment of phytochemical content in human milk during different stages of lactation.

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Song, Brian J; Jouni, Zeina E; Ferruzzi, Mario G

2013-01-01

The present study reports the presence of several carotenoids and flavonoids in human milk samples. Samples were collected from 17 women who delivered healthy term babies (≥ 37 wk of gestation) at 1-, 4-, and 13-wk postpartum intervals. Epicatechin (63.7-828.5 nmol/L), epicatechin gallate (55.7-645.6 nmol/L), epigallocatechin gallate (215.1-2364.7 nmol/L), naringenin (64.1-722.0 nmol/L), kaempferol (7.8-71.4 nmol/L), hesperetin (74.8-1603.1 nmol/L), and quercetin (32.5-108.6 nmol/L) were present in human milk samples with high inter-/intraindividual variability. With the exception of kaempferol, the mean flavonoid content in human milk was not statistically different among lactation stages. In contrast, carotenoids α-carotene (59.0-23.2 nmol/L), β-carotene (164.3-88.0 nmol/L), α-cryptoxanthin (30.6-13.5 nmol/L), β-cryptoxanthin (57.4-24.8 nmol/L), zeaxanthin (46.3-21.4 nmol/L), lutein (121.2-56.4 nmol/L), and lycopene (119.9-49.5 nmol/L) significantly decreased from weeks 1 to 13 of lactation. The observed differences in the relative concentrations of the two phytochemical classes in human milk may be a result of several factors, including dietary exposure, stability in the milk matrix, efficiency of absorption/metabolism, and transfer from plasma to human milk. These data support the notion that flavonoids, as with carotenoids, are dietary phytochemicals present in human milk and potentially available to breast-fed infants. Copyright © 2013 Elsevier Inc. All rights reserved.

Protective effects of some medicinal plants from Lamiaceae family against beta-amyloid induced toxicity in PC12 cell

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Balali P

2012-10-01

Full Text Available Background: Excessive accumulation of beta-amyliod peptide (Aβ, the major component of senile plaques in Alzheimer's disease (AD, causes neuronal cell death through induction of oxidative stress. Therefore, antioxidants may be of use in the treatment of AD. The medicinal plants from the Lamiaceae family have been widely used in Iranian traditional medicine. These plants contain compounds with antioxidant activity and some species in this family have been reported to have neuroprotective properties. In the present study, methanolic extract of seven plants from salvia and satureja species were evaluated for their protective effects against beta-amyloid induced neurotoxicity.Methods: Aerial parts of the plants were extracted with ethyl acetate and methanol, respectively, by percolation at room temperature and subsequently, methanolic extracts of the plants were prepared. PC12 cells were incubated with different concentrations of the extracts in culture medium 1h prior to incubation with Aβ. Cell toxicity was assessed 24h after addition of Aβ by MTT assay.Results: Satureja bachtiarica, Salvia officinalis and Salvia macrosiphon methanolic extracts exhibited high protective effects against Aβ induced toxicity (P<0.001. Protective effects of Satureja bachtiarica and Salvia officinalis were dose-dependent.Conclusion: The main constituents of these extracts are polyphenolic and flavonoid compounds such as rosmarinic acid, naringenin, apigenin and luteolin which have antioxidant properties and may have a role in neuroprotection. Based on neuroprotective effect of these plants against Aβ induced toxicity, we recommend greater attention to their use in the treatment of Alzheimer disease.

Tobacco expressing pap1 increases the responses to par and uv-a by enhancing soluble sugars and flavonoids and elevating plant protections

International Nuclear Information System (INIS)

Sompornpailin, K.; Kanthang, S.

2015-01-01

Five lines of transgenic tobacco over-expressing Production of Anthocyanin Pigment 1 (PAP1) cDNA were analysis of metabolic response against the radiation and their protection of the plant under tissue culture condition. PAP1 transgenic and wild type (WT) plants were treated with the radiations of photosynthetically activate radiation (PAR) or PAR combined with UV-A. All lines of transgenic significantly increased in amounts of p-coumaric acid, naringenin apigenin more than WT under both treatments. Additional UV-A radiating to plant rose up kaempferol content in WT plant (1.5 times) and in PAP1 transgenics (1.8 times). These transgenic plants treated under both conditions had also increased anthocyanin substances (pelargonidin) with significant value after compared to WT. Content of total soluble sugar (TSS) was related to the content of total flavonoids in transgenic. PAR combined with UV-A had a lower induction of the electrolyte leakage percentage and malondialdehyde (MDA) level in the transgenic leaf tissue compared to WT tissue. The metabolic substance levels were considered on its protection of plant cells. In transgenic tissue, the enhancement of apigenin level strongly diminished the increase level of electrolyte leakage while the levels of TSS, p-coumaric acid and naringinin less affected. Moreover, the increase levels of kaempferol and pelargonidin associated with the decrease level of MDA, while the TSS level reversely responded. The PAP1 transgenic increased response of light by adaptation of their metabolites (TSS, p-coumaric acid and flavonoids) consequently enhance parameter indicating protections of the cell. (author)

A novel solid fluorescence method for the fast determination of quercetin in biological samples based on the quercetin-Al(III) complex imprinted polymer

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Hu, Yufei; Feng, Ting; Li, Gongke

2014-01-01

In this work, a novel solid fluorescence method was proposed and applied to the fast determination of quercetin in urine and onion skin samples by using metal coordination imprinted polymer membrane, which was regarded as a recognition element. The quercetin-Al(III) imprinted polymer was immobilized in the microporous polypropylene fiber membrane via consecutive in situ polymerization. The CIP membrane had the porous, loose and layer upon layer structure. The CIP membrane was characterized by electron microscope photographs, infrared spectra, thermogravimetric analysis and solvent-resistant investigation. The extraction conditions including extraction solvent, extraction time, desorption solvent were optimized. Compared with MIP and NIP membrane, CIP membrane had been proved to be peculiar selective for quercetin even in presence of the structurally similar compounds such as kaempferol, rutin, naringenin and alpinetin. The CIP membrane was characteristic of high selectivity, stable and sensitive response to quercetin in polar environment. Under the optimum condition, there was a linear relationship between the state fluorescent response and the concentration of quercetin. The linear calibration range was over 0.02 mg L-1-0.80 mg L-1 with a detection limit of 5 μg L-1. The method was characteristic of flexible and good repeatability with relative standard deviation (RSD) of 4.1%. The proposed method was also successfully applied for the determination of quercetin in urine and onion skin samples without complicated pretreatment. The recoveries were 84.0-112.4% and RSDs varied from 1.5% to 6.8%. The results obtained by the proposed method agreed well with those obtained by HPLC method.

Metabolite profiling of tomato (Lycopersicon esculentum) using 1H NMR spectroscopy as a tool to detect potential unintended effects following a genetic modification.

Science.gov (United States)

Le Gall, Gwénaëlle; Colquhoun, Ian J; Davis, Adrienne L; Collins, Geoff J; Verhoeyen, Martine E

2003-04-23

The maize transcription factors LC and C1 were simultaneously overexpressed in tomato with the aim of producing lines with increased amounts of flavonols. The metabolite composition of these genetically modified tomatoes has been compared with that of azygous (nonmodified) controls grown side-by-side under the same conditions. It has been possible to observe metabolic changes in both types at different stages of maturity. (1)H NMR spectra showed that the levels of glutamic acid, fructose, and some nucleosides and nucleotides gradually increase from the immature to the ripe stage, whereas some amino acids such as valine and gamma-aminobutyric acid were present in higher amounts in unripe tomatoes. Apart from the significantly increased content of six main flavonoid glycosides (mainly kaempferol-3-O-rutinoside, with additional increases in kaempferol-3,7-di-O-glucoside (1), kaempferol-3-O-rutinoside-7-O-glucoside (2), kaempferol-3-O-glucoside, a dihydrokaempferol-O-hexoside (3), and naringenin-7-O-glucoside), the levels of at least 15 other metabolites were found to be different between the two types of red tomato. Among them were citric acid, sucrose, phenylalanine, and trigonelline. However, although statistically significant, these changes in mean values were relatively minor (less than 3-fold) and within the natural variation that would be observed in a field-grown crop. Nevertheless, this study clearly showed that NMR combined with chemometrics and univariate statistics can successfully trace even small differences in metabolite levels between plants and therefore represents a powerful tool to detect potential unintended effects in genetically modified crops.

Chemical Constituents from the Branches of Carpinus turczaninowii with Antioxidative Activities

International Nuclear Information System (INIS)

Ko, Ha Na; Kim, Jung Mi; Bu, Hee Jung; Lee, Nam Ho

2013-01-01

Eight compounds were identified in ethanol extracts prepared from the branches of C. turczaninowii. The compounds, besides 5 and 6, were isolated for the first time from this woody plant. Pyracrenic acid (4) and quercitrin (8) showed potent DPPH free radical scavenging activities with SC 50 values of 55.2 and 62.4 μM, respectively, where ascorbic acid (SC 50 43.5 μM) was used as a positive control. Compounds 4, 5, 6 and 8 showed strong activities in ABTS + radical scavenging assay, with SC 50 values of 34.1, 42.1, 45.8 and 29.6 μM, respectively. These activities are comparable in potency to ascorbic acid (SC 50 31.6 μM). Based on these results, C. turczaninowii extracts are expected to be useful antioxidative agents, potentially applicable in food or cosmetic industries, based on the results of further studies. Korean hornbeam Carpinus turczaninowii is a deciduous woody plant belonging to the family Betulaceae. This flora is endemic to Korea, and can reach a height of 15 m. In the autumn, the fallen leaves of C. turczaninowii display a beautiful orange-red color and the tree is commonly used for bonsai in Korea. The wood is very hard, dense and fine textured, and has been used for making agricultural tools and furniture. Previous chemical investigation on this plant indicated only the existence of flavonoids such as naringenin and quercetin glycosides from the leaves. We have recently reported the isolation diarylheptanoids possessing anti-inflammatory activities from the ethanol extract of C. turczaninowii

Chemical Constituents from the Branches of Carpinus turczaninowii with Antioxidative Activities

Energy Technology Data Exchange (ETDEWEB)

Ko, Ha Na; Kim, Jung Mi; Bu, Hee Jung; Lee, Nam Ho [Jeju National Univ., Jeju (Korea, Republic of)

2013-08-15

Eight compounds were identified in ethanol extracts prepared from the branches of C. turczaninowii. The compounds, besides 5 and 6, were isolated for the first time from this woody plant. Pyracrenic acid (4) and quercitrin (8) showed potent DPPH free radical scavenging activities with SC{sub 50} values of 55.2 and 62.4 μM, respectively, where ascorbic acid (SC{sub 50} 43.5 μM) was used as a positive control. Compounds 4, 5, 6 and 8 showed strong activities in ABTS{sup +} radical scavenging assay, with SC{sub 50} values of 34.1, 42.1, 45.8 and 29.6 μM, respectively. These activities are comparable in potency to ascorbic acid (SC{sub 50} 31.6 μM). Based on these results, C. turczaninowii extracts are expected to be useful antioxidative agents, potentially applicable in food or cosmetic industries, based on the results of further studies. Korean hornbeam Carpinus turczaninowii is a deciduous woody plant belonging to the family Betulaceae. This flora is endemic to Korea, and can reach a height of 15 m. In the autumn, the fallen leaves of C. turczaninowii display a beautiful orange-red color and the tree is commonly used for bonsai in Korea. The wood is very hard, dense and fine textured, and has been used for making agricultural tools and furniture. Previous chemical investigation on this plant indicated only the existence of flavonoids such as naringenin and quercetin glycosides from the leaves. We have recently reported the isolation diarylheptanoids possessing anti-inflammatory activities from the ethanol extract of C. turczaninowii.

Selective Rayleigh light scattering determination of trace quercetin with silver nanoparticles

Energy Technology Data Exchange (ETDEWEB)

Usoltseva, Liliya O.; Samarina, Tatiana O. [Department of Chemistry, M.V.Lomonosov Moscow State University, 119991 GSP-1 Moscow (Russian Federation); Abramchuk, Sergei S. [Nesmeyanov Institute of Organoelement Compounds (INEOS), Russian Academy of Sciences, Vavilova 28, Moscow 119991 (Russian Federation); Prokhorova, Aleksandra F. [Department of Chemistry, M.V.Lomonosov Moscow State University, 119991 GSP-1 Moscow (Russian Federation); Beklemishev, Mikhail K., E-mail: mkb@analyt.chem.msu.ru [Department of Chemistry, M.V.Lomonosov Moscow State University, 119991 GSP-1 Moscow (Russian Federation)

2016-11-15

Rayleigh light scattering (RLS) is a simple technique with a high potential of sensitive determination of small organic molecules. We have found that ppb amounts of quercetin (Qu) greatly enhance the RLS of the solution of silver nanoparticles (AgNPs) stabilized with cetyltrimethylammonium bromide (CTAB) or sodium n-dodecyl sulfate (SDS). Enhancement of light scattering is observed only in the presence of an excess of AgNO{sub 3}, which implies that it is a result of nanoparticle growth; another reason for the enhanced scattering is the aggregation of AgNPs by the analyte that was confirmed by dynamic light scattering technique. The conditions were chosen for the determination of Qu in aqueous solution with the detection limits of 0.01 and 0.03 μmol L{sup −1} and linear ranges of 0.1–1.3 and 0.1–2.0 μmol L{sup −1} for SDS- and CTAB-stabilized AgNPs, respectively; the intra-day RSDs did not exceed 7%. Unexpectedly, other bioflavonoids (rutin, dihydroquercetin, and naringenin) did not change the signal of Qu and did not interfere with its determination in 1:1 M ratio (0.5 μmol L{sup −1} each). Other compounds (asparagin, uric acid, urea and some inorganic ions) were also tolerated in high amounts. - Highlights: • Low concentrations of quercetin enhance the light scattering by silver nanoparticles. • Main processes are aggregation, nanoparticle growth and formation of new particles. • Other compounds exert a weaker effect on the light scattering signal.

Development of an ultra-fast liquid chromatography-tandem mass spectrometry method for simultaneous determination of seven flavonoids in rat plasma: Application to a comparative pharmacokinetic investigation of Ginkgo biloba extract and single pure ginkgo flavonoids after oral administration.

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Wang, Tianyang; Xiao, Jie; Hou, Huiping; Li, Pei; Yuan, Ziyue; Xu, Huarong; Liu, Ran; Li, Qing; Bi, Kaishun

2017-08-15

For deeper pharmacokinetic investigation and further curative application of ginkgo flavonoids, a delicate, efficient and precise UFLC-MS/MS technique for synchronous quantitation of seven flavonoids, apigenin, luteolin, naringenin, quercetin, diosmetin, kaempferol and isorhamnetin in rat plasma has been established. After mixing with the internal standard (IS) linarin, bio-samples were pretreated via ethyl acetate for liquid-liquid extraction, then isolated at 0.2ml/min flow rate on a Venusil MP C 18 chromatographic column (100mm×2.1mm, 3μm) by means of gradient elution. 0.1% formic acid-water and methanol system was used as the mobile phase. Mass spectrometric inspection was conducted on a 4000Q UFLC-MS/MS system with turbo ion spray source in patterns of negative ion and multiple reaction-monitoring (MRM). All calibration curves proved favorable linearity (R 2 ≥0.9918) in linear ranges. Intra-day and inter-day precisions didn't exceed 14.0% for all the analytes, and the accuracy was within 6.9%. Extraction recoveries of analytes and IS were less than ±15.0% of nominal concentrations. This method has been under thorough and firm verification for a comparative pharmacokinetic research after gavage between Ginkgo biloba extract and single pure ginkgo flavonoids. The results demonstrated that there're evident pharmacokinetic discrepancies, and possible structural influences were innovatively proposed. Generally, substitution with 3-hydroxylation, a double bond in ring C, ring B methoxylation often confer longer onset period. The existence of ring B catechol group gives rise to faster clearance. Copyright © 2017. Published by Elsevier B.V.

Phytochemical analysis of Vernonanthura tweedieana and a validated UPLC-PDA method for the quantification of eriodictyol

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Layzon Antonio Lemos da Silva

Full Text Available AbstractVernonanthura tweedieana (Baker H. Rob., Asteraceae, is used in the Brazilian folk medicine for the treatment of respiratory diseases. In this work the phytochemical investigation of its ethanol extracts as well as the development and validation of an UPLC-PDA method for the quantification of the eriodictyol from the leaves were performed. The phytochemical study for this species lead to the identification of ethyl caffeate, naringenin and chrysoeriol in mixture, eriodictyol from leaves, and the mixture of 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl-propan-1-one and evofolin B, apigenin, the mixture of caffeic and protocatechuic acid and luteolin from stems with roots, being reported for the first time for V. tweedieana, except for eriodictyol. The structural elucidation of all isolated compounds was achieved by 1H and 2D NMR spectroscopy, and in comparison with published data. An UPLC-PDA method for quantification of the eriodictyol in leaves of V. tweedieana was developed and validated for specificity, linearity, precision (repeatability and intermediate precision, limit of detection (LOD and limit of quantification (LOQ, accuracy and robustness. In this study, an excellent linearity was obtained (r2 = 0.9999, good precision (repeatability RSD = 2% and intermediate precision RSD = 8% and accuracy (average recovery from 98.6% to 99.7%. The content of eriodictyol in the extract of leaves of V. tweedieana was 41.40 ± 0.13 mg/g. Thus, this study allowed the optimization of a simple, fast and validated UPLC-PDA method which can be used to support the quality assessment of this herbal material.

Enhanced oral bioavailability of docetaxel in rats combined with myricetin: In situ and in vivo evidences.

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Hao, Tianyun; Ling, Yunni; Wu, Meijuan; Shen, Yajing; Gao, Yu; Liang, Shujun; Gao, Yuan; Qian, Shuai

2017-04-01

The purpose of this study was to investigate the effect of myricetin on the pharmacokinetics of docetaxel in rats. In comparison to oral docetaxel alone (40mg/kg), the bioavailability of docetaxel could be significantly enhanced by 1.6-2.4-fold via oral co-administration with various flavonoids (apigenin, naringenin, baicalein, quercetin and myricetin) at a dosage of 10mg/kg, and myricetin showed the highest bioavailability improvement. Further pharmacokinetic studies demonstrated that the presence of myricetin (5-20mg/kg) enhanced both C max and AUC of docetaxel with the highest C max (162ng/mL, 2.3-fold) and relative bioavailability (244%) achieved at 10mg/kg of myricetin, while t 1/2 was not influenced. In order to explore the reasons for such bioavailability enhancement of docetaxel, rat in situ single-pass intestinal perfusion model and intravenous docetaxel co-administrated with oral myricetin were carried out. After combining with myricetin, the permeability coefficient (P blood ) of docetaxel based on its appearance in mesenteric blood was significantly increased up to 3.5-fold in comparison to that of docetaxel alone. Different from oral docetaxel, the intravenous pharmacokinetics of docetaxel was not affected by co-administration of myricetin, indicating the limited effect of myricetin on the elimination of docetaxel. The above findings suggested that the oral bioavailability enhancement of docetaxel via co-administration with myricetin might be mainly attributed to the enhanced absorption in gastrointestinal tract rather than modulating the elimination of docetaxel. Copyright © 2017 Elsevier B.V. All rights reserved.

Flavonoid Composition of Tarocco (Citrus sinensis L. Osbeck) Clone "Lempso" and Fast Antioxidant Activity Screening by DPPH-UHPLC-PDA-IT-TOF.

Science.gov (United States)

Sommella, Eduardo; Pagano, Francesco; Pepe, Giacomo; Ostacolo, Carmine; Manfra, Michele; Chieppa, Marcello; Di Sanzo, Rosa; Carabetta, Sonia; Campiglia, Pietro; Russo, Mariateresa

2017-11-01

Clonal selection and hybridisation are valid strategies to obtain fruits with enhanced sensorial and nutraceutical properties. Within Citrus sinensis varieties, Tarocco clone "Lempso" is a typical product of the Calabria region (Italy) characterised by its red pulp. This is the first report concerning its accurate profiling. To characterise in detail the flavonoid composition of Lempso clone and to compare its antioxidant potential with other Citrus varieties by a fast screening method. Extracts were subjected to solid phase extraction and the qualitative/quantitative profile was elucidated through ultra-high performance liquid chromatography (UHPLC) coupled to photodiode array (PDA) and ion trap time-of-flight (IT-TOF) mass spectrometry detection, and compared to both Cleopatra mandarin (Citrus reticulata) and blood orange (Citrus sinensis (L.) Osbeck) Sanguinello varieties. The antioxidant activity was assessed by pre-column 2,2'-diphenyl-1-picrylhydrazyl (DPPH) reaction coupled to UHPLC-PDA. Lempso is characterised by flavonoids (17) and anthocyanins (8). Flavanones content (Hesperidin: 57.19 ± 0.49, Vicenin-2: 4.59 ± 0.03, Narirutin: 5.78 ± 0.13 mg/100 mL) was considerably higher than Cleopatra and Sanguinello varieties. The developed DPPH-UHPLC-PDA method provides information regarding the single contributions to antioxidant activity, highlighting how Ferulic acid, Quercetin and Cyanidin derivatives possess considerable radical scavenging activity (> 50%). The total antioxidant activity was also evaluated and compared with positive controls, showing higher scavenging activity than Cleopatra and Sanguinello (IC 50 : 333.76 ± 10.81 μg/mL vs. 452.62 ± 10.81 and 568.39 ± 26.98 μg/mL, respectively). These data evidence the nutraceutical potential of Lempso variety, which could be an ingredient for functional beverages. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

Extraction and quantification of polyphenols from kinnow (Citrus reticulate L. peel using ultrasound and maceration techniques

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Muhammad N. Safdar

2017-07-01

Full Text Available An investigation was carried out to extract polyphenols from the peel of kinnow (Citrus reticulate L. by maceration and ultrasound-assisted extraction (UAE techniques. The antioxidant potential of these polyphenols was evaluated using ferric reducing antioxidant power (FRAP, 2,2-diphenyl-1-picrylhydrazyl (DPPH, and superoxide radical scavenging assays; and their antimicrobial activity was assessed against bacterial strains Staphyloccoccus aureus, Bacillus cereus, and Salmonella typhimurium. The highest extraction yield was obtained through the solvent ethanol at 80% concentration level, whereas UAE was a more efficient technique and yielded comparatively higher polyphenol contents than maceration. Maximum polyphenols were extracted with 80% methanol [32.48 mg gallic acid equivalent (GAE/g extract] using UAE, whereas minimum phenolics (8.64 mg GAE/g extract were obtained with 80% ethyl acetate through the maceration technique. Elevated antioxidant activity of kinnow peel extracts was exhibited in three antioxidant assays, where 80% methanolic extracts showed the highest antioxidant activity (27.67±1.11mM/100 g for FRAP and the highest scavenging activity, 72.83±0.65% and 64.80±0.91% for DPPH and superoxide anion radical assays, respectively. Strong correlations between total polyphenols and antioxidant activity were recorded. Eleven phenolic compounds—including five phenolic acids and six flavonoids—were identified and quantified by high performance liquid chromatography. Ferulic acid and hesperidin were the most abundant compounds whereas caffeic acid was the least abundant phenolic compound in kinnow peel extracts. Maximum inhibition zone was recorded against S. aureus (16.00±0.58 mm whereas minimum inhibition zone was noted against S. typhimurium (9.00±1.16 mm. It was concluded that kinnow mandarin peels, being a potential source of phenolic compounds with antioxidant and antimicrobial properties, may be used as an ingredient for

Identifying candidate agents for lung adenocarcinoma by walking the human interactome

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Sun Y

2016-09-01

Full Text Available Yajiao Sun,1 Ranran Zhang,2 Zhe Jiang,1 Rongyao Xia,1 Jingwen Zhang,1 Jing Liu,1 Fuhui Chen1 1Department of Respiratory, The Second Affiliated Hospital of Harbin Medical University, 2Department of Respiratory, Harbin First Hospital, Harbin, People’s Republic of China Abstract: Despite recent advances in therapeutic strategies for lung cancer, mortality is still increasing. Therefore, there is an urgent need to identify effective novel drugs. In the present study, we implement drug repositioning for lung adenocarcinoma (LUAD by a bioinformatics method followed by experimental validation. We first identified differentially expressed genes between LUAD tissues and nontumor tissues from RNA sequencing data obtained from The Cancer Genome Atlas database. Then, candidate small molecular drugs were ranked according to the effect of their targets on differentially expressed genes of LUAD by a random walk with restart algorithm in protein–protein interaction networks. Our method identified some potentially novel agents for LUAD besides those that had been previously reported (eg, hesperidin. Finally, we experimentally verified that atracurium, one of the potential agents, could induce A549 cells death in non-small-cell lung cancer-derived A549 cells by an MTT assay, acridine orange and ethidium bromide staining, and electron microscopy. Furthermore, Western blot assays demonstrated that atracurium upregulated the proapoptotic Bad and Bax proteins, downregulated the antiapoptotic p-Bad and Bcl-2 proteins, and enhanced caspase-3 activity. It could also reduce the expression of p53 and p21Cip1/Waf1 in A549 cells. In brief, the candidate agents identified by our approach may provide greater insights into improving the therapeutic status of LUAD. Keywords: lung adenocarcinoma, drug repositioning, bioinformatics, protein–protein interaction network, atracurium

4-methoxychalcone enhances cisplatin-induced oxidative stress and cytotoxicity by inhibiting the Nrf2/ARE-mediated defense mechanism in A549 lung cancer cells.

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Lim, Juhee; Lee, Sung Ho; Cho, Sera; Lee, Ik-Soo; Kang, Bok Yun; Choi, Hyun Jin

2013-10-01

Nuclear factor erythroid 2-related factor 2 (Nrf2) is a key transcriptional regulator for the protection of cells against oxidative and xenobiotic stresses. Recent studies have demonstrated that high constitutive expression of Nrf2 is observed in many types of cancer cells showing resistance to anti-cancer drugs, suggesting that the suppression of overexpressed Nrf2 could be an attractive therapeutic strategy to overcome cancer drug resistance. In the present study, we aimed to find small molecule compounds that enhance the sensitivity of tumor cells to cisplatin induced cytotoxicity by suppressing Nrf2-mediated defense mechanism. A549 lung cancer cells were shown to be more resistant to the anti-cancer drug cisplatin than HEK293 cells, with higher Nrf2 signaling activity; constitutively high amounts of Nrf2-downstream target proteins were observed in A549 cells. Among the three chalcone derivatives 4-methoxy-chalcone (4-MC), hesperidin methylchalcone, and neohesperidin dihydrochalcone, 4-MC was found to suppress transcriptional activity of Nrf2 in A549 cells but to activate it in HEK293 cells. 4-MC was also shown to down-regulate expression of Nrf2 and the downstream phase II detoxifying enzyme NQO1 in A549 cells. The PI3K/Akt pathway was found to be involved in the 4-MC-induced inhibition of Nrf2/ARE activity in A549 cells. This inhibition of Nrf2 signaling results in the accelerated generation of reactive oxygen species and exacerbation of cytotoxicity in cisplatin-treated A549 cells. Taken together, these results suggest that the small molecule compound 4-MC could be used to enhance the sensitivity of tumor cells to the therapeutic effect of cisplatin through the regulation of Nrf2/ARE signaling.

Evaluation of Bioactive Compounds, Pharmaceutical Quality, and Anticancer Activity of Curry Leaf (Murraya koenigii L.

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Ali Ghasemzadeh

2014-01-01

Full Text Available In this study, we investigated some bioactive compounds and pharmaceutical qualities of curry leaf (Murraya koenigii L. extracts from three different locations in Malaysia. The highest TF and total phenolic (TP contents were observed in the extracts from Kelantan (3.771 and 14.371 mg/g DW, followed by Selangor (3.146 and 12.272 mg/g DW and Johor (2.801 and 12.02 mg/g DW, respectively. High quercetin (0.350 mg/g DW, catechin (0.325 mg/g DW, epicatechin (0.678 mg/g DW, naringin (0.203 mg/g DW, and myricetin (0.703 mg/g DW levels were observed in the extracts from Kelantan, while the highest rutin content (0.082 mg/g DW was detected in the leaves from Selangor. The curry leaf extract from Kelantan exhibited higher concentration of gallic acid (0.933 mg/g DW than that from Selangor (0.904 mg/g DW and Johor (0.813 mg/g DW. Among the studied samples, the ones from Kelantan exhibited the highest radical scavenging activity (DPPH, 66.41% and ferric reduction activity potential (FRAP, 644.25 μm of Fe(II/g followed by those from Selangor (60.237% and 598.37 μm of Fe(II/g and Johor (50.76% and 563.42 μm of Fe(II/g, respectively. A preliminary screening showed that the curry leaf extracts from all the locations exhibited significant anticarcinogenic effects inhibiting the growth of breast cancer cell line (MDA-MB-231 and maximum inhibition of MDA-MB-231 cell was observed with the curry leaf extract from Kelantan. Based on these results, it is concluded that Malaysian curry leaf collected from the North (Kelantan might be potential source of potent natural antioxidant and beneficial chemopreventive agents.

Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.

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Mao, Zhonghua; Gan, Chunli; Zhu, Jiuxin; Ma, Nan; Wu, Lijun; Wang, Libo; Wang, Xiaobo

2017-06-15

We have successfully established AS model using thoracic aortas vascular ring which evaluated by the morphological changes of blood vessels, the proliferation of VSMC, and the expression of inflammation factors VEGF, CRP, JNK2 and p38. This AS model has the advantages of low cost, convenient and short period of established time. Moreover, we investigated the anti-AS activities of 7 flavonoids Narirutin (1), Naringin (2), Eriodictyol (3), Luteolin (4), Galuteolin (5), Astragalin (6), Kaempferol (7) from flowers of Helichrysum arenarium L. MOENCH by examining the vascular morphology, the inhibition on the expression of inflammation factors CRP, VEGF, JNK2, p38. In addition, we investigated the anti-AS activities of these 7 flavonoids by examining NO secretion of RAW264.7 cells in response to LPS. All above inflammation factors have been proved to be involved in the formation of AS. After comprehensive analysis of all results to discuss the structure-activity relationship, we summarized the conclusions at follow: compounds 1-7 could inhibit the expression of VEGF, CRP, JNK2, p38 and NO at different level, and we evaluated that flavonol aglycone have more significant anti-inflammation than it's glycoside, and the anti-AS activity of flavonols were stronger than flavanones and flavones, which means that 3-group might be the effective group. Eventually, we supposed the main anti-inflammatory mechanism of these compounds was to reduce the expression of CRP, inhibit the kinases activity of JNK2 and p38, and then the MAPK pathway was suppressed, which resulted in the decrease of NO synthesis, VEGF expression and endothelial adhesion factor expression. And eventually, the scar tissue and vascular stenosis formations were prevented. This conclusion suggested flavonoids have the potential of preventing AS formation. Copyright © 2017 Elsevier Ltd. All rights reserved.

Evaluation of Bioactive Compounds, Pharmaceutical Quality, and Anticancer Activity of Curry Leaf (Murraya koenigii L.).

Science.gov (United States)

Ghasemzadeh, Ali; Jaafar, Hawa Z E; Rahmat, Asmah; Devarajan, Thiyagu

2014-01-01

In this study, we investigated some bioactive compounds and pharmaceutical qualities of curry leaf (Murraya koenigii L.) extracts from three different locations in Malaysia. The highest TF and total phenolic (TP) contents were observed in the extracts from Kelantan (3.771 and 14.371 mg/g DW), followed by Selangor (3.146 and 12.272 mg/g DW) and Johor (2.801 and 12.02 mg/g DW), respectively. High quercetin (0.350 mg/g DW), catechin (0.325 mg/g DW), epicatechin (0.678 mg/g DW), naringin (0.203 mg/g DW), and myricetin (0.703 mg/g DW) levels were observed in the extracts from Kelantan, while the highest rutin content (0.082 mg/g DW) was detected in the leaves from Selangor. The curry leaf extract from Kelantan exhibited higher concentration of gallic acid (0.933 mg/g DW) than that from Selangor (0.904 mg/g DW) and Johor (0.813 mg/g DW). Among the studied samples, the ones from Kelantan exhibited the highest radical scavenging activity (DPPH, 66.41%) and ferric reduction activity potential (FRAP, 644.25  μ m of Fe(II)/g) followed by those from Selangor (60.237% and 598.37  μ m of Fe(II)/g) and Johor (50.76% and 563.42  μ m of Fe(II)/g), respectively. A preliminary screening showed that the curry leaf extracts from all the locations exhibited significant anticarcinogenic effects inhibiting the growth of breast cancer cell line (MDA-MB-231) and maximum inhibition of MDA-MB-231 cell was observed with the curry leaf extract from Kelantan. Based on these results, it is concluded that Malaysian curry leaf collected from the North (Kelantan) might be potential source of potent natural antioxidant and beneficial chemopreventive agents.

Evaluation of Bioactive Compounds, Pharmaceutical Quality, and Anticancer Activity of Curry Leaf (Murraya koenigii L.)

Science.gov (United States)

Ghasemzadeh, Ali; Jaafar, Hawa Z. E.; Rahmat, Asmah; Devarajan, Thiyagu

2014-01-01

In this study, we investigated some bioactive compounds and pharmaceutical qualities of curry leaf (Murraya koenigii L.) extracts from three different locations in Malaysia. The highest TF and total phenolic (TP) contents were observed in the extracts from Kelantan (3.771 and 14.371 mg/g DW), followed by Selangor (3.146 and 12.272 mg/g DW) and Johor (2.801 and 12.02 mg/g DW), respectively. High quercetin (0.350 mg/g DW), catechin (0.325 mg/g DW), epicatechin (0.678 mg/g DW), naringin (0.203 mg/g DW), and myricetin (0.703 mg/g DW) levels were observed in the extracts from Kelantan, while the highest rutin content (0.082 mg/g DW) was detected in the leaves from Selangor. The curry leaf extract from Kelantan exhibited higher concentration of gallic acid (0.933 mg/g DW) than that from Selangor (0.904 mg/g DW) and Johor (0.813 mg/g DW). Among the studied samples, the ones from Kelantan exhibited the highest radical scavenging activity (DPPH, 66.41%) and ferric reduction activity potential (FRAP, 644.25 μm of Fe(II)/g) followed by those from Selangor (60.237% and 598.37 μm of Fe(II)/g) and Johor (50.76% and 563.42 μm of Fe(II)/g), respectively. A preliminary screening showed that the curry leaf extracts from all the locations exhibited significant anticarcinogenic effects inhibiting the growth of breast cancer cell line (MDA-MB-231) and maximum inhibition of MDA-MB-231 cell was observed with the curry leaf extract from Kelantan. Based on these results, it is concluded that Malaysian curry leaf collected from the North (Kelantan) might be potential source of potent natural antioxidant and beneficial chemopreventive agents. PMID:24693327

An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers

International Nuclear Information System (INIS)

Schutte, Maaike E.; Freidig, Andreas P.; Sandt, Johannes J.M. van de; Alink, Gerrit M.; Rietjens, Ivonne M.C.M.; Groten, John P.

2006-01-01

The present study describes the effect of different flavonoids on the absorption of the pro-carcinogen PhIP through Caco-2 monolayers and the development of an in silico model describing this process taking into account passive diffusion and active transport of PhIP. Various flavonoids stimulated the apical to basolateral PhIP transport. Using the in silico model for flavone, kaempferol and chrysoeriol, the apparent Ki value for inhibition of the active transport to the apical side was estimated to be below 53 μM and for morin, robinetin and taxifolin between 164 and 268 μM. For myricetin, luteolin, naringenin and quercetin, the apparent Ki values were determined more accurately and amounted to 37.3, 12.2, 11.7 and 5.6 μM respectively. Additional experiments revealed that the apical to basolateral PhIP transport was also increased in the presence of a typical BCRP or MRP inhibitor with apparent Ki values in the same range as those of the flavonoids. This observation together with the fact that flavonoids are known to be inhibitors of MRPs and BCRP, corroborates that inhibition of these apical membrane transporters is involved in the flavonoid-mediated increased apical to basolateral PhIP transport. Based on the apparent Ki values obtained, it is concluded that the flavonols, at the levels present in the regular Western diet, are capable of stimulating the transport of PhIP through Caco-2 monolayers from the apical to the basolateral compartment. This points to flavonoid-mediated stimulation of the bioavailability of PhIP and, thus, a possible adverse effect of these supposed beneficial food ingredients

Evaluation of the antioxidant activity of Betula pendula leaves extract and its effects on model foods.

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Azman, Nurul Aini Mohd; Skowyra, Monika; Muhammad, Kwestan; Gallego, María Gabriela; Almajano, Maria Pilar

2017-12-01

Betula pendula Roth (Betulaceae) exhibits many pharmacological activities in humans including anticancer, antibacterial, and antiviral effects. However, the antioxidant activity of BP towards lipid degradation has not been fully determined. The BP ethanol and methanol extracts were evaluated to determine antioxidant activity by an in vitro method and lyophilized extract of BP was added to beef patties to study oxidative stability. Antioxidant activities of extracts of BP were determined by measuring scavenging radical activity against methoxy radical generated by Fenton reaction 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid (TEAC) radical cation, the oxygen radical absorbance capacity (ORAC) and the ferric reducing antioxidant power (FRAP) assays. The lipid deterioration in beef patties containing 0.1% and 0.3% (w/w) of lyophilized extract of BP stored in 80:20 (v/v) O 2 :CO 2 modified atmosphere (MAP) at 4 °C for 10 days was determined using thiobarbituric acid reacting substances (TBARS), % metmyoglobin and colour value. The BP methanol extract revealed the presence of catechin, myricetin, quercetin, naringenin, and p-coumaric acid. The BP ethanol (50% w/w) extract showed scavenging activity in TEAC, ORAC and FRAP assays with values of 1.45, 2.81, 1.52 mmol Trolox equivalents (TE)/g DW, respectively. Reductions in lipid oxidation were found in samples treated with lyophilized BP extract (0.1% and 0.3% w/w) as manifested by the changes of colour and metmyoglobin concentration. A preliminary study film with BP showed retard degradation of lipid in muscle food. The present results indicated that the BP extracts can be used as natural food antioxidants.

SULT1A3-Mediated Regiospecific 7-O-Sulfation of Flavonoids in Caco-2 Cells Can Be Explained by the Relevant Molecular Docking Studies

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Meng, Shengnan; Wu, Baojian; Singh, Rashim; Yin, Taijun; Morrow, John Kenneth; Zhang, Shuxing; Hu, Ming

2012-01-01

Flavonoids are the polyphenolic compounds with various claimed health benefits, but the extensive metabolism by uridine-5'-diphospho-glucuronosyltransferases (UGTs) and sulfotransferases (SULTs) in liver and intestine led to poor oral bioavailabilities. The effects of structural changes on the sulfonation of flavonoids have not been systemically determined, although relevant effects of structural changes on the glucuronidation of flavonoids had. We performed the regiospecific sulfonation of sixteen flavonoids from five different subclasses of flavonoids, which are represented by apigenin (flavone), genistein (isoflavone), naringenin (flavanone), kaempherol (flavonol), and phloretin (chalcone). Additional studies were performed using 4 mono-hydroxyl flavonoids with –OH group at 3, 4’, 5 or 7 position, followed by 5 di-hydroxyl-flavonoids, and 2 tri-hydroxyl flavonoids by using expressed human SULT1A3 and Caco-2 cell lysates. We found that these compounds were exclusively sulfated at the 7-OH position by SULT1A3 and primarily sulfated at 7-OH position in Caco-2 cell lysates with minor amounts of 4’-O-sulfates formed as well. Sulfonation rates measured using SULT1A3 and Caco-2 cell lysates were highly correlated at substrate concentrations of 2.5 and 10 µM. Molecular docking studies provided structural explanations as to why sulfonation only occurred at the 7-OH position of flavones, flavonols and flavanones. In conclusion, molecular docking studies explain why SULT1A3 exclusively mediates sulfonation at the 7-OH position of flavones/flavonols, and correlation studies indicate that SULT1A3 is the main isoform responsible for flavonoid sulfonation in the Caco-2 cells. PMID:22352375

Protections of bovine serum albumin protein from damage on functionalized graphene-based electrodes by flavonoids.

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Sun, Bolu; Gou, Yuqiang; Xue, Zhiyuan; Zheng, Xiaoping; Ma, Yuling; Hu, Fangdi; Zhao, Wanghong

2016-05-01

A sensitive electrochemical sensor based on bovine serum albumin (BSA)/poly (diallyldimethylammonium chloride) (PDDA) functionalized graphene nanosheets (PDDA-G) composite film modified glassy carbon electrode (BSA/PDDA-G/GCE) had been developed to investigate the oxidative protein damage and protections of protein from damage by flavonoids. The performance of this sensor was remarkably improved due to excellent electrical conductivity, strong adsorptive ability, and large effective surface area of PDDA-G. The BSA/PDDA-G/GCE displayed the greatest degree of BSA oxidation damage at 40 min incubation time and in the pH 5.0 Fenton reagent system (12.5 mM FeSO4, 50 mM H2O2). The antioxidant activities of four flavonoids had been compared by fabricated sensor based on the relative peak current ratio of SWV, because flavonoids prevented BSA damage caused by Fenton reagent and affected the BSA signal in a solution containing Co(bpy)3(3+). The sensor was characterized by cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), and scanning electron microscopy (SEM). UV-vis spectrophotometry and FTIR were also used to investigate the generation of hydroxyl radical and BSA damage, respectively. On the basis of results from electrochemical methods, the order of the antioxidant activities of flavonoids is as follows: (+)-catechin>kaempferol>apigenin>naringenin. A novel, direct SWV analytical method for detection of BSA damage and assessment of the antioxidant activities of four flavonoids was developed and this electrochemical method provided a simple, inexpensive and rapid detection of BSA damage and evaluation of the antioxidant activities of samples. Copyright © 2016 Elsevier B.V. All rights reserved.

Chemical analyses and in vitro and in vivo toxicity of fruit methanol extract of Sechium edule var. nigrum spinosum.

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Aguiñiga-Sánchez, Itzen; Cadena-Íñiguez, Jorge; Santiago-Osorio, Edelmiro; Gómez-García, Guadalupe; Mendoza-Núñez, Víctor Manuel; Rosado-Pérez, Juana; Ruíz-Ramos, Mirna; Cisneros-Solano, Víctor Manuel; Ledesma-Martínez, Edgar; Delgado-Bordonave, Angel de Jesus; Soto-Hernández, Ramón Marcos

2017-12-01

Sechium edule (Jacq.) Sw. (Cucurbitaceae) is used in ethnomedicine, but the diversity of the varietal groups of this species has not often been considered. This is important because we previously reported that different variety of species exhibit different activities across different tumor cell lines. This study investigates the chemical composition and biological activities of extracts obtained from S. edule var. nigrum spinosum. The leukemia P388 cell line and mononuclear bone marrow cells (MNCBMs) were treated with the extract at a concentration ranging from 40 to 2370 μg/mL for cytotoxicity and viability assays. CD-1 mice were treated with 8-5000 mg/kg extract and monitored every hour for the first 24 h and subsequently for seven days for signs of toxicity (LD 50 ). In addition, the chromatographic profile of the extract was determined by HPLC. The extract inhibits the proliferation of both P388 cells and MNCBMs, with IC 50 values of 927 and 1911 μg/mL, respectively, but reduced the viability and induced the apoptosis of only leukemia cells. The LD 50 was higher than 5000 mg/kg, and this concentration did not alter the blood chemistry or cell count but doubled the mitotic index in the bone marrow. The HPLC showed the presence of cucurbitacins, phloridzin, naringenin, phloretin, apigenin, and gallic, chlorogenic, vanillic, p-hydroxybenzoic, caffeic, and p-coumaric acids. Sechium edule var. nigrum spinosum contains bioactive compounds that explain the antiproliferative and nutraceutical activities, and its lack of physiological side effects constitutes an added value to a widely consumed vegetable.