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Sample records for surface flavonoid aglycones

  1. High-performance liquid chromatographic separation of surface flavonoid aglycones in Artemisia annua L. and Artemisia vulgaris L.

    OpenAIRE

    STEPHANKA IVANCHEVA; RENETA GEVRENOVA; MILENA NIKOLOVA

    2004-01-01

    External flavonoid aglycones from Artemisia annua L. and Artemisia vulgaris L. were analyzed by the HPLC method. The mobile phase was composed of t-butanol-methanol-20 mmol l-1 phosphate buffer, pH 3.22. The linear gradient elution method within 22 min was applied. The main aglycones in A. annua and A. vulgaris are methyl ethers of quercetagetin and quercetin. Quercetagetin 3,6,7-trimethyl ether in A. annua and quercetin 3,7,3-trimethyl ether in A. vulgaris are the most abundant compounds.

  2. High-performance liquid chromatographic separation of surface flavonoid aglycones in Artemisia annua L. and Artemisia vulgaris L.

    Directory of Open Access Journals (Sweden)

    STEPHANKA IVANCHEVA

    2004-07-01

    Full Text Available External flavonoid aglycones from Artemisia annua L. and Artemisia vulgaris L. were analyzed by the HPLC method. The mobile phase was composed of t-butanol-methanol-20 mmol l-1 phosphate buffer, pH 3.22. The linear gradient elution method within 22 min was applied. The main aglycones in A. annua and A. vulgaris are methyl ethers of quercetagetin and quercetin. Quercetagetin 3,6,7-trimethyl ether in A. annua and quercetin 3,7,3’-trimethyl ether in A. vulgaris are the most abundant compounds.

  3. Molecular displacement of warfarin from human serum albumin by flavonoid aglycones

    Energy Technology Data Exchange (ETDEWEB)

    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.

  4. Molecular displacement of warfarin from human serum albumin by flavonoid aglycones

    International Nuclear Information System (INIS)

    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

  5. The cranberry flavonoids PAC DP-9 and quercetin aglycone induce cytotoxicity and cell cycle arrest and increase cisplatin sensitivity in ovarian cancer cells

    Science.gov (United States)

    WANG, YIFEI; HAN, ALEX; CHEN, EVA; SINGH, RAKESH K.; CHICHESTER, CLINTON O.; MOORE, RICHARD G.; SINGH, AJAY P.; VORSA, NICHOLI

    2015-01-01

    Cranberry flavonoids (flavonols and flavan-3-ols), in addition to their antioxidant properties, have been shown to possess potential in vitro activity against several cancers. However, the difficulty of isolating cranberry compounds has largely limited anticancer research to crude fractions without well-defined compound composition. In this study, individual cranberry flavonoids were isolated to the highest purity achieved so far using gravity and high performance column chromatography and LC-MS characterization. MTS assay indicated differential cell viability reduction of SKOV-3 and OVCAR-8 ovarian cancer cells treated with individual cranberry flavonoids. Treatment with quercetin aglycone and PAC DP-9, which exhibited the strongest activity, induced apoptosis, led to caspase-3 activation and PARP deactivation, and increased sensitivity to cisplatin. Furthermore, immunofluorescence microscopy and western blot study revealed reduced expression and activation of epidermal growth factor receptor (EGFR) in PAC DP-9 treated SKOV-3 cells. In addition, quercetin aglycone and PAC DP-9 deactivated MAPK-ERK pathway, induced downregulation of cyclin D1, DNA-PK, phosphohistone H3 and upregulation of p21, and arrested cell cycle progression. Overall, this study demonstrates promising in vitro cytotoxic and anti-proliferative properties of two newly characterized cranberry flavonoids, quercetin aglycone and PAC DP-9, against ovarian cancer cells. PMID:25776829

  6. Phenological Variations in the Surface Flavonoids of Artemisia vulgaris L. and Artemisia absinthium L.

    OpenAIRE

    NIKOLOVA, Milena; VELICKOVIC, Dragan

    2007-01-01

    Qualitative and quantitative variations in the surface flavonoids in relation to phenological development of Artemisia vulgaris L. and Artemisia absinthium L. were examined. Plant material was harvested at different phenological stages (vegetative, before budding, floral budding, flowering, and fruiting) of the life cycle of the species. In A. vulgaris and A. absinthium acetone exudates, 6 and 4 flavonoid aglycones were identified, respectively, by TLC analysis. Quercetin 3,7,3'-trim...

  7. A simple and rapid infrared-assisted self enzymolysis extraction method for total flavonoid aglycones extraction from Scutellariae Radix and mechanism exploration.

    Science.gov (United States)

    Wang, Liping; Duan, Haotian; Jiang, Jiebing; Long, Jiakun; Yu, Yingjia; Chen, Guiliang; Duan, Gengli

    2017-09-01

    A new, simple, and fast infrared-assisted self enzymolysis extraction (IRASEE) approach for the extraction of total flavonoid aglycones (TFA) mainly including baicalein, wogonin, and oroxylin A from Scutellariae Radix is presented to enhance extraction yield. Extraction enzymolysis temperature, enzymolysis liquid-to-solid ratio, enzymolysis pH, enzymolysis time and infrared power, the factors affecting IRASEE procedure, were investigated in a newly designed, temperature-controlled infrared-assisted extraction (TC-IRAE) system to acquire the optimum analysis conditions. The results illustrated that IRASEE possessed great advantages in terms of efficiency and time compared with other conventional extraction techniques. Furthermore, the mechanism of IRASEE was preliminarily explored by observing the microscopic change of the samples surface structures, studying the main chemical compositions change of the samples before and after extraction and investigating the kinetics and thermodynamics at three temperature levels during the IRASEE process. These findings revealed that IRASEE can destroy the surface microstructures to accelerate the mass transfer and reduce the activation energy to intensify the chemical process. This integrative study presents a simple, rapid, efficient, and environmental IRASEE method for TFA extraction which has promising prospects for other similar herbal medicines. Graphical Abstract ᅟ.

  8. Structure related effects of flavonoid aglycones on cell cycle progression of HepG2 cells: Metabolic activation of fisetin and quercetin by catechol-O-methyltransferase (COMT).

    Science.gov (United States)

    Poór, Miklós; Zrínyi, Zita; Kőszegi, Tamás

    2016-10-01

    Dietary flavonoids are abundant in the Plant Kingdom and they are extensively studied because of their manifold pharmacological activities. Recent studies highlighted that cell cycle arrest plays a key role in their antiproliferative effect in different tumor cells. However, structure-activity relationship of flavonoids is poorly characterized. In our study the influence of 18 flavonoid aglycones (as well as two metabolites) on cell cycle distribution was investigated. Since flavonoids are extensively metabolized by liver cells, HepG2 tumor cell line was applied, considering the potential metabolic activation/inactivation of flavonoids. Our major observations are the followings: (1) Among the tested compounds diosmetin, fisetin, apigenin, lutelin, and quercetin provoked spectacular extent of G2/M phase cell cycle arrest. (2) Inhibition of catechol-O-methyltransferase enzyme by entacapone decreased the antiproliferative effects of fisetin and quercetin. (3) Geraldol and isorhamnetin (3'-O-methylated metabolites of fisetin and quercetin, respectively) demonstrated significantly higher antiproliferative effect on HepG2 cells compared to the parent compounds. Based on these results, O-methylated flavonoid metabolites or their chemically modified derivatives may be suitable candidates of tumor therapy in the future. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  9. A new estimation of the total flavonoids in silkworm cocoon sericin layer through aglycone determination by hydrolysis-assisted extraction and HPLC-DAD analysis

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    Jin-Ge Zhao

    2016-03-01

    Full Text Available Background: Silk sericin and a few non-protein components isolated from the cocoon layer including two silk proteins in silkworm Bombyx mori has many bioactivities. The dietary sericin possess antinatural oxidation, anticancer, antihyperlipidemic, and antidiabetic activities. The non-protein components surrounding the sericin layer involve in wax, pigments mainly meaning flavonoids, sugars, and other impurities. However, very few investigations have reported the estimation of the total flavonoids derived from the cocoon layer. The flavonoids are commonly present in their glycosylated forms and mostly exist as quercetin glycosides in the sericin layers of silkworm cocoons. Objective: The aim of this study was to find a more accurate method to estimate the level of the total flavonoids in silkworm cocoons. Design: An efficient procedure of hydrolysis-assisted extraction (HAE was first established to estimate the level of the total flavonoids through the determination of their aglycones, quercetin, and kaempferol. Then, a comparison was made between traditional colorimetric method and our method. In addition, the antioxidant activities of hydrolysis-assisted extract sample were determined. Results: The average contents of quercetin and kaempferol were 1.98 and 0.42 mg/g in Daizo cocoon. Their recoveries were 99.56 and 99.17%. The total sum of quercetin and kaempferol was detected to be 2.40±0.07 mg/g by HAE-HPLC, while the total flavonoids (2.59±0.48 mg/g estimated by the traditional colorimetric method were only equivalent to 1.28±0.04 mg/g of quercetin. The HAE sample also exhibits that IC50 values of scavenging ability of diphenyl picryl hydrazinyl (DPPH radical and hydroxyl radical (HO· are 243.63 µg/mL and 4.89 mg/mL, respectively. Conclusions: These results show that the HAE-HPLC method is specificity of cocoon and far superior to the colorimetric method. Therefore, this study has profound significance for the comprehensive utilization

  10. Flavonoid-membrane Interactions: A Protective Role of Flavonoids at the Membrane Surface?

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    Patricia I. Oteiza

    2005-01-01

    Full Text Available Flavonoids can exert beneficial health effects through multiple mechanisms. In this paper, we address the important, although not fully understood, capacity of flavonoids to interact with cell membranes. The interactions of polyphenols with bilayers include: (a the partition of the more non-polar compounds in the hydrophobic interior of the membrane, and (b the formation of hydrogen bonds between the polar head groups of lipids and the more hydrophilic flavonoids at the membrane interface. The consequences of these interactions are discussed. The induction of changes in membrane physical properties can affect the rates of membrane lipid and protein oxidation. The partition of certain flavonoids in the hydrophobic core can result in a chain breaking antioxidant activity. We suggest that interactions of polyphenols at the surface of bilayers through hydrogen bonding, can act to reduce the access of deleterious molecules (i.e. oxidants, thus protecting the structure and function of membranes.

  11. Flavonoids and the CNS

    DEFF Research Database (Denmark)

    Jäger, Anna Katharina; Saaby, Lasse

    2011-01-01

    Flavonoids are present in almost all terrestrial plants, where they provide UV-protection and colour. Flavonoids have a fused ring system consisting of an aromatic ring and a benzopyran ring with a phenyl substituent. The flavonoids can be divided into several classes depending on their structure....... Flavonoids are present in food and medicinal plants and are thus consumed by humans. They are found in plants as glycosides. Before oral absorption, flavonoids undergo deglycosylation either by lactase phloridzin hydrolase or cytosolic ß-glucocidase. The absorbed aglycone is then conjugated by methylation......, sulphatation or glucuronidation. Both the aglycones and the conjugates can pass the blood-brain barrier. In the CNS several flavones bind to the benzodiazepine site on the GABA(A)-receptor resulting in sedation, anxiolytic or anti-convulsive effects. Flavonoids of several classes are inhibitors of monoamine...

  12. Optimization of the extraction of flavonoids from grape leaves by response surface methodology

    International Nuclear Information System (INIS)

    Brad, K.; Liu, W.

    2013-01-01

    The extraction of flavonoids from grape leaves was optimized to maximize flavonoids yield in this study. A central composite design of response surface methodology involving extracting time, power, liquid-solid ratio, and concentration was used, and second-order model for Y was employed to generate the response surfaces. The optimum condition for flavonoids yield was determined as follows: extracting time 24.95 min, power 72.05, ethanol concentration 63.35%, liquid-solid ratio 10.04. Under the optimum condition, the flavonoids yield was 76.84 %. (author)

  13. 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

    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...

  14. Optimization of Total Flavonoids Extraction from Coreopsis tinctoria Nutt. by Response Surface Methodology

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    Liu, X. F.

    2014-11-01

    Full Text Available Response surface methodology (RSM was applied to predict optimum conditions for extraction of flavonoid from Coreopsis tinctoria Nutt. A central composite design (CCD was used to monitor the effect of extraction temperature, extraction time, and water-to-material ratio on yield of total flavonoids. The optimal extraction conditions were obtained as water-to-material ratio of 55 ml g−1, extraction temperature of 80 °C and extraction time of 70 minutes. Under these conditions, the average total flavonoids yield, according to the mass of raw material, was 9.0 ± 0.6 %, which corresponds to the predicted value of 8.9 %. Thus, the extraction method was applied successfully to extract total flavonoids from C. tinctoria.

  15. Flavonoids and the CNS

    Directory of Open Access Journals (Sweden)

    Anna K. Jäger

    2011-02-01

    Full Text Available Flavonoids are present in almost all terrestrial plants, where they provide UV-protection and colour. Flavonoids have a fused ring system consisting of an aromatic ring and a benzopyran ring with a phenyl substituent. The flavonoids can be divided into several classes depending on their structure. Flavonoids are present in food and medicinal plants and are thus consumed by humans. They are found in plants as glycosides. Before oral absorption, flavonoids undergo deglycosylation either by lactase phloridzin hydrolase or cytosolic β-glucocidase. The absorbed aglycone is then conjugated by methylation, sulphatation or glucuronidation. Both the aglycones and the conjugates can pass the blood-brain barrier. In the CNS several flavones bind to the benzodiazepine site on the GABAA-receptor resulting in sedation, anxiolytic or anti-convulsive effects. Flavonoids of several classes are inhibitors of monoamine oxidase A or B, thereby working as anti-depressants or to improve the conditions of Parkinson’s patients. Flavanols, flavanones and anthocyanidins have protective effects preventing inflammatory processes leading to nerve injury. Flavonoids seem capable of influencing health and mood.

  16. Flavonoid-modified surfaces: multifunctional bioactive biomaterials with osteopromotive, anti-inflammatory, and anti-fibrotic potential.

    Science.gov (United States)

    Córdoba, Alba; Satué, María; Gómez-Florit, Manuel; Hierro-Oliva, Margarita; Petzold, Christiane; Lyngstadaas, Staale P; González-Martín, María Luisa; Monjo, Marta; Ramis, Joana M

    2015-03-11

    Flavonoids are small polyphenolic molecules of natural origin with antioxidant, anti-inflammatory, and antibacterial properties. Here, a bioactive surface based on the covalent immobilization of flavonoids taxifolin and quercitrin on titanium substrates is presented, using (3-aminopropyl)triethoxysilane (APTES) as coupling agent. FTIR and XPS measurements confirm the grafting of the flavonoids to the surfaces. Using 2-aminoethyl diphenylborinate (DPBA, a flavonoid-specific dye), the modified surfaces are imaged by fluorescence microscopy. The bioactivity of the flavonoid-modified surfaces is evaluated in vitro with human umbilical cord derived mesenchymal stem cells (hUC-MSCs) and human gingival fibroblasts (HGFs) and compared to that of simple flavonoid coatings prepared by drop casting. Flavonoid-modified surfaces show anti-inflammatory and anti-fibrotic potential on HGF. In addition, Ti surfaces covalently functionalized with flavonoids promote the differentiation of hUC-MSCs to osteoblasts--enhancing the expression of osteogenic markers, increasing alkaline phosphatase activity and calcium deposition; while drop-casted surfaces do not. These findings could have a high impact in the development of advanced implantable medical devices like bone implants. Given the broad range of bioactivities of flavonoid compounds, these surfaces are ready to be explored for other biomedical applications, e.g., as stent surface or tumor-targeted functionalized nanoparticles for cardiovascular or cancer therapies. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  17. Flavonoid variation in Eurasian Sedum and Sempervivum

    NARCIS (Netherlands)

    Stevens, J.F; 't Hart, H; Elema, E.T; Bolck, A

    Flavonoids from vegetative parts of 29 species of Eurasian Sedum, Sedum meyeri-johannis from central East Africa, 34 species of Sempervivum, and Jovibarba heuffelii have been identified after acid hydrolysis. Ten flavonoid aglycones were detected, i.e. kaempferol, herbacetin, sexangularetin,

  18. Flavonoids from Teucrium fruticans L.

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    Wanda Kisiel

    2014-01-01

    Full Text Available From aerial parts of Teucrium fncticans L. three flavonoids were isolated and identified as 5-hydroxy-6, 7, 3', 4'-tetramethoxyflavone, 5, 4'-dihydroxy-6, 7, 3'-trimethoxyflavone (cirsilineol and 5, 4'-dihydroxy-6, 7-dimethoxyflavone (cirsimaritin. The former compound was found to be a predominant flavone aglycone constituent of the plant material. This is the first report on the isolation of flavonoids from the plant.

  19. Flavonoids Extraction from Taraxacum officinale (Dandelion: Optimisation Using Response Surface Methodology and Antioxidant Activity

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    Zongxi Sun

    2014-01-01

    Full Text Available The Box-Behnken design combined with response surface method was employed to optimize ultrasonic-assisted extraction of flavonoids from Taraxacum officinale. The optimized results showed that the highest extraction yield with ultrasonic-assisted extraction could reach 2.62% using 39.6% (v/v ethanol and 59.5 : 1 (mL/g liquid-solid ratio for 43.8 min. The crude extract was then purified by HPD-100 macroporous adsorption resin, and the flavonoids content in the purified extract increased to 54.7%. The antioxidant activity of the purified flavonoids was evaluated in vitro by scavenging capacity of ABTS or DPPH, β-carotene bleaching, and FTC test. The knowledge obtained from this study should be useful to further develop and apply this plant resource.

  20. Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes

    DEFF Research Database (Denmark)

    Justesen, U.; Knuthsen, Pia

    2001-01-01

    , coriander, cress, dill, lemon balm, lovage, oregano, parsley, rosemary, sage, spearmint, tarragon, thyme, and watercress) were analysed by HPLC and mass spectrometry. Five major flavonoid aglycones were detected and quantified by HPLC after acid hydrolysis: apigenin, isorhamnetin, kaempferol, luteolin...

  1. Some new external flavonoids from American ferns

    Energy Technology Data Exchange (ETDEWEB)

    Wollenweber, E.

    1979-01-01

    American gymnogrammoid ferns have been analysed for the flavonoid aglycones present in frond exudates. They are predominantly methylated chalcones, dihydrochalcones, flavones, and flavonols, occurring mostly as farinose deposit (''ceraceous indument''). This is the first report of external flavonoids on Pterozonium species; a chalcone has been identified. On Cheilanthes kaulfussii and Cheilanthes viscida traces of flavonoid aglycones are observed, dissolved in lipophilic exudate material. On Pellaea longimucronata a flavonol is found even on leaves which appear glaucous. 2',4',6'-Trihydroxychalcone is found for the second time in the plant kingdom on Adiantum sulphureum. Galangin-3,7-dimethylether is found as a new natural flavonol on Cheilanthes kaulfussii. In addition, samples of Pityrogramma chrysoconia and Pit. triangularis var. maxonii have been investigated. The results indicate chemotaxonomic implication of flavonoid patterns.

  2. LC-ESI-QTOF-MS based screening and identification of isomeric jujubogenin and pseudojujubogenin aglycones in Bacopa monnieri extract.

    Science.gov (United States)

    Nuengchamnong, Nitra; Sookying, Sontaya; Ingkaninan, Kornkanok

    2016-09-10

    Bacopa monnieri (L.) Wettst. (Scrophulariaceae) is an Ayurvedic medicinal plant used as a memory enhancer. Its major chemical constituents are Bacopa saponins consisting of jujubogenin and pseudojujubogenin glycosides. These two aglycones are isomers different at the positions of prenyl substitution i.e., at C-23 for jujubogenin and at C-22 for pseudojujubogenin. In this study, we demonstrate the rapid and comprehensive characterization of saponin glycosides in B. monnieri using liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometer (LC-ESI-QTOF-MS). This shows that ESI-QTOF-MS in positive-ion mode, jujubogenin and pseudojujubogenin glycosides could be discriminated by the peak abundance ratio of m/z 455 [Aglycone+H-H2O](+) to m/z of 473 [Aglycone+H](+). Furthermore, the sequence of sugar moieties can be observed. In a similar manner, the isomeric saponins; deoxyjujubogenin and deoxypseudojujubogenin glycosides can be distinguished using the m/z 437[Aglycone+H-H2O](+) and m/z 455[Aglycone+H](+) peak ratio. Use of the negative-ion mode with MS/MS fragmentation can provide information about the type of sugar linked to the aglycone i.e., at m/z 633 (aglycone+glucose) or at m/z 603 (aglycone+arabinose). With our method, 62 chemical constituents in B. monnieri including saponin glycosides, flavonoids, and alkaloids were identified. This is the first systematic study in structural characterization on isomeric saponins and other metabolites in B. monnieri using ESI-QTOF-MS. Copyright © 2016 Elsevier B.V. All rights reserved.

  3. Response surface optimization of ultrasound-assisted flavonoids extraction from the flower of Citrus aurantium L. var. amara Engl.

    Science.gov (United States)

    Yang, Li; Cao, Ya-Lan; Jiang, Jian-Guo; Lin, Qing-Sheng; Chen, Jian; Zhu, Liang

    2010-05-01

    Citrus aurantium L. var. amara Engl is a member of genus Citrus (Rutaceae) and has been used in Chinese medicine with the effectiveness of digestant and expectorant. Ultrasonic-assisted extraction process for maximum flavonoids from the flower of Citrus aurantium L. var. amara Engl was investigated by response surface methodology. Through single factor experiment, ranges of the main variables (including ethanol concentration, solid/liquid ratio, extraction time and temperature) affecting the extraction yield of flavonoids were confirmed. Box-Behnken central composite design consisting of 24 experimental runs and 5 replicates at zero point was then applied and a regress model was obtained to predict the optimal extraction yield. The ANOVA indicated that the regression equation fits very well with the actual situation, reflecting the relationship between the extraction yield of flavonoids and extraction conditions. The optimal conditions were as follows: extraction temperature 72.11 degrees C, time 51.89 min, ethanol concentration 51.19% and liquid/solid ratio of 40:10. Under the optimal conditions, the maximum response value of yield (1.88%) was consistent with the experimental value (1.87%), indicating the feasibility and validation of response surface methodology in optimizing the extraction of flavonoids from the flower of Citrus aurantium L. var. amara Engl.

  4. Optimization of Ultrasonic-Assisted Extraction of Flavonoid Compounds and Antioxidants from Alfalfa Using Response Surface Method.

    Science.gov (United States)

    Jing, Chang-Liang; Dong, Xiao-Fang; Tong, Jian-Ming

    2015-08-26

    Ultrasonic-assisted extraction (UAE) was used to extract flavonoid-enriched antioxidants from alfalfa aerial part. Response surface methodology (RSM), based on a four-factor, five-level central composite design (CCD), was employed to obtain the optimal extraction parameters, in which the flavonoid content was maximum and the antioxidant activity of the extracts was strongest. Radical scavenging capacity of the extracts, which represents the amounts of antioxidants in alfalfa, was determined by using 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonicacid) (ABTS) and 2,2'-diphenyl-1-picrylhydrazyl (DPPH) methods. The results showed good fit with the proposed models for the total flavonoid extraction (R² = 0.9849), for the antioxidant extraction assayed by ABTS method (R² = 0.9764), and by DPPH method (R² = 0.9806). Optimized extraction conditions for total flavonoids was a ratio of liquid to solid of 57.16 mL/g, 62.33 °C, 57.08 min, and 52.14% ethanol. The optimal extraction parameters of extracts for the highest antioxidant activity by DPPH method was a ratio of liquid to solid 60.3 mL/g, 54.56 °C, 45.59 min, and 46.67% ethanol, and by ABTS assay was a ratio of liquid to solid 47.29 mL/g, 63.73 °C, 51.62 min, and 60% ethanol concentration. Our work offers optimal extraction conditions for total flavonoids and antioxidants from alfalfa.

  5. Inhibitory Activities of Antioxidant Flavonoids from Tamarix gallica on Amyloid Aggregation Related to Alzheimer's and Type 2 Diabetes Diseases.

    Science.gov (United States)

    Ben Hmidene, Asma; Hanaki, Mizuho; Murakami, Kazuma; Irie, Kazuhiro; Isoda, Hiroko; Shigemori, Hideyuki

    2017-01-01

    The prevention of amyloid aggregation is promising for the treatment of age-related diseases such as Alzheimer's (AD) and type 2 diabetes (T2D). Ten antioxidant flavonoids isolated from the medicinal halophyte Tamarix gallica were tested for their amyloid aggregation inhibition potential. Glucuronosylated flavonoids show relatively strong inhibitory activity of Amyloid β (Aβ) and human islet amyloid polypeptide (hIAPP) aggregation compared to their aglycone analogs. Structure-activity relationship of the flavonoids suggests that the catechol moiety is important for amyloid aggregation inhibition, while the methylation of the carboxyl group in the glucuronide moiety and of the hydroxyl group in the aglycone flavonoids decreased it.

  6. Transgenic rice seed expressing flavonoid biosynthetic genes accumulate glycosylated and/or acylated flavonoids in protein bodies

    Science.gov (United States)

    Ogo, Yuko; Mori, Tetsuya; Nakabayashi, Ryo; Saito, Kazuki; Takaiwa, Fumio

    2016-01-01

    Plant-specialized (or secondary) metabolites represent an important source of high-value chemicals. In order to generate a new production platform for these metabolites, an attempt was made to produce flavonoids in rice seeds. Metabolome analysis of these transgenic rice seeds using liquid chromatography-photodiode array-quadrupole time-of-flight mass spectrometry was performed. A total of 4392 peaks were detected in both transgenic and non-transgenic rice, 20–40% of which were only detected in transgenic rice. Among these, 82 flavonoids, including 37 flavonols, 11 isoflavones, and 34 flavones, were chemically assigned. Most of the flavonols and isoflavones were O-glycosylated, while many flavones were O-glycosylated and/or C-glycosylated. Several flavonoids were acylated with malonyl, feruloyl, acetyl, and coumaroyl groups. These glycosylated/acylated flavonoids are thought to have been biosynthesized by endogenous rice enzymes using newly synthesized flavonoids whose biosynthesis was catalysed by exogenous enzymes. The subcellular localization of the flavonoids differed depending on the class of aglycone and the glycosylation/acylation pattern. Therefore, flavonoids with the intended aglycones were efficiently produced in rice seeds via the exogenous enzymes introduced, while the flavonoids were variously glycosylated/acylated by endogenous enzymes. The results suggest that rice seeds are useful not only as a production platform for plant-specialized metabolites such as flavonoids but also as a tool for expanding the diversity of flavonoid structures, providing novel, physiologically active substances. PMID:26438413

  7. The influence of phase II conjugation on the biological activity of flavonoids

    NARCIS (Netherlands)

    Beekmann, K.

    2016-01-01

    Flavonoid consumption is often correlated with a wide range of health effects, such as the prevention of cardiovascular diseases, neurodegenerative diseases, and diabetes. These effects are usually ascribed to the activity of the parent flavonoid aglycones, even though these forms of the

  8. [Effect of flavonoids on the composition of surface glycopolymers in Azospirillum lipoferum Sp59b].

    Science.gov (United States)

    Kanevskiĭ, M V; Konnova, S A; Boĭko, A S; Fedonenko, Iu P; Sigida, E N; Ignatov, V V

    2014-01-01

    Cultivation of the type strain Azospirillum lipoferum Sp59b in the presence of the flavonoid quercetin induced modification of the structure of the bacterial lipopolysaccharide. Cultivation in the presence of the flavonoid was shown to result in altered serological characteristics of the bacteria, increased heterogeneity of the outer membrane lipopolysaccharide pool, as well as in modified composition and fatty acid ratio of lipid A. The flavonoid was shown to induce the synthesis of the O-specific polysaccharide with the repeating structure represented by a tetrasaccharide consisting of a linear trisaccharide fragment of α-L-Rhap residues in the main chain and the terminal β-D-Glcp residue. The structure of this O-specific polysaccharide was identical to the previously determined structure of the capsular polysaccharide of these bacteria grown without quercetin. Modifications in the structural composition of the capsular polysaccharide induced by cultivation in the presence of quercetin were revealed.

  9. 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...

  10. Flavonoids as fruit and vegetable intake biomarkers

    DEFF Research Database (Denmark)

    Krogholm, Kirstine Suszkiewicz

    calculation of the bivariate correlation coefficients is the common approach when using only one reference method. Back in 2002, a strictly controlled dietary intervention study indicated that the sum of 7 different flavonoid aglycones excreted in 24h urine samples potentially could be used as a biomarker...... and cohort studies. The Ph.D. thesis contains four scientific papers. Paper I provides evidence that the sum of 7 flavonoids in 24h urine respond in a linear and sensitive manner to moderate increases in the intake of fruits and vegetables, and thus consolidates that the flavonoids are a valid biomarker...... of fruit and vegetable intakes. In Paper I, the urinary recovery of the 7 flavonoids in morning spot urine (i.e. all urine voids from midnight including the first morning void) was also found to respond to moderate increases in the intake of fruits and vegetables. However, the association was somewhat...

  11. Effects of Teucrium polium spp. capitatum flavonoids on the lipid and carbohydrate metabolism in rats

    DEFF Research Database (Denmark)

    Stefkov, Gjoshe; Kulevanova, Svetlana; Miova, Biljana

    2011-01-01

    - and streptozotocin hyperglycemic rats. Results and discussion: HPLC analyses revealed several flavonoids: luteolin, apigenin, cirsiliol, diosmetin, cirsimaritin and cirsilineol as both free aglycons and glycosides. The extract and mixture of commercial flavonoids showed a distinct insulinotropic effect on INS-1E...... glycogen and tended to normalize the activity of gluconeogenic enzymes. Conclusion: The results demonstrate that examined plant extracts contain flavonoids with insulinotropic and antihyperglycemic effects....

  12. The maize tapetum employs diverse mechanisms to synthesize and store proteins and flavonoids and transfer them to the pollen surface.

    Science.gov (United States)

    Li, Yubing; Suen, Der Fen; Huang, Chien-Yu; Kung, Shung-Yee; Huang, Anthony H C

    2012-04-01

    In anthers, the tapetum synthesizes and stores proteins and flavonoids, which will be transferred to the surface of adjacent microspores. The mechanism of synthesis, storage, and transfer of these pollen-coat materials in maize (Zea mays) differs completely from that reported in Arabidopsis (Arabidopsis thaliana), which stores major pollen-coat materials in tapetosomes and elaioplasts. On maize pollen, three proteins, glucanase, xylanase, and a novel protease, Zea mays pollen coat protease (ZmPCP), are predominant. During anther development, glucanase and xylanase transcripts appeared at a mid developmental stage, whereas protease transcript emerged at a late developmental stage. Protease and xylanase transcripts were present only in the anther tapetum of the plant, whereas glucanase transcript was distributed ubiquitously. ZmPCP belongs to the cysteine protease family but has no closely related paralogs. Its nascent polypeptide has a putative amino-terminal endoplasmic reticulum (ER)-targeting peptide and a propeptide. All three proteins were synthesized in the tapetum and were present on mature pollen after tapetum death. Electron microscopy of tapetum cells of mid to late developmental stages revealed small vacuoles distributed throughout the cytoplasm and numerous secretory vesicles concentrated near the locular side. Immunofluorescence microscopy and subcellular fractionation localized glucanase in ER-derived vesicles in the cytoplasm and the wall facing the locule, xylanase in the cytosol, protease in vacuoles, and flavonoids in subdomains of ER rather than in vacuoles. The nonoverlapping subcellular locations of the three proteins and flavonoids indicate distinct modes of their storage in tapetum cells and transfer to the pollen surface, which in turn reflect their respective functions in tapetum cells or the pollen surface.

  13. Fruit-surface flavonoid accumulation in tomato is controlled by a SlMYB12-regulated transcriptional network.

    Directory of Open Access Journals (Sweden)

    Avital Adato

    2009-12-01

    Full Text Available The cuticle covering plants' aerial surfaces is a unique structure that plays a key role in organ development and protection against diverse stress conditions. A detailed analysis of the tomato colorless-peel y mutant was carried out in the framework of studying the outer surface of reproductive organs. The y mutant peel lacks the yellow flavonoid pigment naringenin chalcone, which has been suggested to influence the characteristics and function of the cuticular layer. Large-scale metabolic and transcript profiling revealed broad effects on both primary and secondary metabolism, related mostly to the biosynthesis of phenylpropanoids, particularly flavonoids. These were not restricted to the fruit or to a specific stage of its development and indicated that the y mutant phenotype is due to a mutation in a regulatory gene. Indeed, expression analyses specified three R2R3-MYB-type transcription factors that were significantly down-regulated in the y mutant fruit peel. One of these, SlMYB12, was mapped to the genomic region on tomato chromosome 1 previously shown to harbor the y mutation. Identification of an additional mutant allele that co-segregates with the colorless-peel trait, specific down-regulation of SlMYB12 and rescue of the y phenotype by overexpression of SlMYB12 on the mutant background, confirmed that a lesion in this regulator underlies the y phenotype. Hence, this work provides novel insight to the study of fleshy fruit cuticular structure and paves the way for the elucidation of the regulatory network that controls flavonoid accumulation in tomato fruit cuticle.

  14. [Optimization on preparation of hawthorn fruit total flavonoids-phospholipid complex using Plackett-Burman design, central composite design and response surface methodology].

    Science.gov (United States)

    Shi, Ya-Jun; Wu, Pin-Jiang; Wei, Ping

    2010-03-01

    To choose the optimal conditions for the formation of the complex with total flavonoids in hawthorn fruit and phospholipid. Solvent evaporation process was used to prepare hawthorn total flavonoids phospholipid complex. The evaluation criterion was the complex ratio. The experiment inspected the significance of influential factor of preparation technology by Plackett-Burman design and optimized significance of factor and level with the central composite design. The binomial and linear equations were fitted to the data of overall desirabilities, and the resulting equation was used to produce 3-D response surface graphs, through which the optimal formulation was predicted. The ratio of total flavonoids to phospholipid, flavonoids concentration and reaction temperature had significant influence on the craft. It was showed that the correlation coefficient of second-order quadratic model was high. The correlation coefficient reached 0.9886. The optimum conditions for the preparation of the complex were as follows: phospholipids/total flavonoids was 3 : 1, the temperature was 40 degrees C and the concentration of principal agent was 10 mg/mL The deviation between the result of the best craft verification test and the binomial fitting equation forecast value was less than 2.0%. Response surface methodology is successfully used to optimize the preparation of total flavonoids in hawthorn phospholipid complex. The optimized process is reliable, stable and available for the industrial production.

  15. Development of Phaleria macrocarpa (Scheff.) Boerl Fruits Using Response Surface Methodology Focused on Phenolics, Flavonoids and Antioxidant Properties.

    Science.gov (United States)

    Mohamed Mahzir, Khurul Ain; Abd Gani, Siti Salwa; Hasanah Zaidan, Uswatun; Halmi, Mohd Izuan Effendi

    2018-03-22

    In this study, the optimal conditions for the extraction of antioxidants from the Buah Mahkota Dewa fruit ( Phaleria macrocarpa) was determined by using Response Surface Methodology (RSM). The optimisation was applied using a Central Composite Design (CCD) to investigate the effect of three independent variables, namely extraction temperature (°C), extraction time (minutes) and extraction solvent to-feed ratio (% v / v ) on four responses: free radical scavenging activity (DPPH), ferric ion reducing power assay (FRAP), total phenolic content (TPC) and total flavonoid content (TFC). The optimal conditions for the antioxidants extraction were found to be 64 °C extraction temperature, 66 min extraction time and 75% v / v solvent to-feed ratio giving the highest percentage yields of DPPH, FRAP, TPC and TFC of 86.85%, 7.47%, 292.86 mg/g and 3.22 mg/g, respectively. Moreover, the data were subjected to Response Surface Methodology (RSM) and the results showed that the polynomial equations for all models were significant, did not show lack of fit, and presented adjusted determination coefficients ( R ²) above 99%, proving that the yield of phenolic, flavonoid and antioxidants activities obtained experimentally were close to the predicted values and the suitability of the model employed in RSM to optimise the extraction conditions. Hence, in this study, the fruit from P. macrocarpa could be considered to have strong antioxidant ability and can be used in various cosmeceutical or medicinal applications.

  16. Protein-Flavonoid Interaction Studies by a Taylor Dispersion Surface Plasmon Resonance (SPR Technique: A Novel Method to Assess Biomolecular Interactions

    Directory of Open Access Journals (Sweden)

    Preejith P. Vachali

    2016-02-01

    Full Text Available Flavonoids are common polyphenolic compounds widely distributed in fruits and vegetables. These pigments have important pharmacological relevance because emerging research suggests possible anti-cancer and anti-inflammatory properties as well other beneficial health effects. These compounds are relatively hydrophobic molecules, suggesting the role of blood transport proteins in their delivery to tissues. In this study, we assess the binding interactions of four flavonoids (kaempferol, luteolin, quercetin, and resveratrol with human serum albumin (HSA, the most abundant protein in the blood, and with glutathione S-transferase pi isoform-1 (GSTP1, an enzyme with well-characterized hydrophobic binding sites that plays an important role in detoxification of xenobiotics with reduced glutathione, using a novel Taylor dispersion surface plasmon resonance (SPR technique. For the first time, HSA sites revealed a high-affinity binding site for flavonoid interactions. Out of the four flavonoids that we examined, quercetin and kaempferol showed the strongest equilibrium binding affinities (KD of 63 ± 0.03 nM and 37 ± 0.07 nM, respectively. GSTP1 displayed lower affinities in the micromolar range towards all of the flavonoids tested. The interactions of flavonoids with HSA and GSTP1 were studied successfully using this novel SPR assay method. The new method is compatible with both kinetic and equilibrium analyses.

  17. Flavonoid accumulation patterns of transparent testa mutants of arabidopsis

    Science.gov (United States)

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

    2001-01-01

    Flavonoids have been implicated in the regulation of auxin movements in Arabidopsis. To understand when and where flavonoids may be acting to control auxin movement, the flavonoid accumulation pattern was examined in young seedlings and mature tissues of wild-type Arabidopsis. Using a variety of biochemical and visualization techniques, flavonoid accumulation in mature plants was localized in cauline leaves, pollen, stigmata, and floral primordia, and in the stems of young, actively growing inflorescences. In young Landsberg erecta seedlings, aglycone flavonols accumulated developmentally in three regions, the cotyledonary node, the hypocotyl-root transition zone, and the root tip. Aglycone flavonols accumulated at the hypocotyl-root transition zone in a developmental and tissue-specific manner with kaempferol in the epidermis and quercetin in the cortex. Quercetin localized subcellularly in the nuclear region, plasma membrane, and endomembrane system, whereas kaempferol localized in the nuclear region and plasma membrane. The flavonoid accumulation pattern was also examined in transparent testa mutants blocked at different steps in the flavonoid biosynthesis pathway. The transparent testa mutants were shown to have precursor accumulation patterns similar to those of end product flavonoids in wild-type Landsberg erecta, suggesting that synthesis and end product accumulation occur in the same cells.

  18. Optimization of ultrasound-assisted extraction of flavonoids compounds from Chenopodium hybridum L. stem with response surface methodology

    Science.gov (United States)

    Wu, Y.; Hu, H. B.; Wang, C. L.; Ma, S. R.; Zhang, L. L.

    2016-08-01

    Ultrasound-assisted extraction (UAE) of flavonoids compounds (FC) from the stem of Chenopodium hybridum L.(C.hybridum L.) was investigated in this paper. Significant technological parameters were screened and optimized by using Plackett-Burman (PB) design, Steepest ascent method and Box-Behnken (BB) design, respectively. A mathematical model with high correlation coefficient (R2=0.9896) was developed and showed good consistency between the experimental and predicted values. The optimum conditions for UAE were obtained by res- ponse surface methodology (RSM) as follows: volumn fraction of ethanol 76.62 %, extractive temperature 78.69°C, and liquid to solid ratio 58.43 for 30 min. Under these conditions, total flavo- noid content (TFC) of 9.4701 mg RE/100g were gained and it was closely related with predi- cted value (9.4640 mg RE/100g) and indicated the suitability of the developed model.

  19. UV radiation dependent flavonoid accumulation of Cistus laurifolius L

    International Nuclear Information System (INIS)

    Vogt, T.; Gülz, P.-G.; Reznik, H.

    1991-01-01

    Epicuticular and intracellular flavonoids of Cistus laurifolius grown with and without UV radiation in a phytotron as well as under natural garden conditions in the field were studied. The amount of intracellular flavonoid glycosides of leaves receiving UV-A radiation was two fold higher than that measured in the absence o f UV-A radiation, whether grown in the phytotron or in the field. Exposure of previously protected leaves to UV-A radiation increased the intracellular flavonoid glycoside content to that of unprotected leaves. The qualitative composition of intracellular flavonoid glycosides showed a reduced amount of quercetin-3-galactoside to the myricetin monosides when the leaves were grown without UV-A radiation in the field and in the phytotron. Epicuticular flavonoid aglycones were not influenced by UV radiation significantly. (author)

  20. Isoflavone aglycone content and the thermal, functional, and structural properties of soy protein isolates prepared from hydrothermally treated soybeans.

    Science.gov (United States)

    Wally-Vallim, Ana Paula; Vanier, Nathan Levien; Zavareze, Elessandra da Rosa; Zambiazi, Rui Carlos; de Castro, Luis Antônio Suita; Schirmer, Manoel Artigas; Elias, Moacir Cardoso

    2014-07-01

    Soybeans were hydrothermally treated at 2 different temperatures (40 °C and 60 °C) and for 4 different hydration times (4, 8, 12, and 16 h) to (i) increase the isoflavone aglycone content in a soy protein isolate and (ii) evaluate the changes in thermal, functional, and structural properties of a soy protein isolate as a function of hydrothermal treatment conditions. Our study is the first to evaluate aglycone content, extraction yield, β-glucosidase activity, differential scanning calorimetry, protein digestibility, scanning electron microscopy, water absorption capacity (WAC), foaming capacity (FC), and foaming stability of soy protein isolates prepared from hydrothermally treated soybeans. For aglycone enhancement and the extraction yield maintenance of soy protein isolates, the condition of 40 °C for 12 h was the best soybean hydrothermal treatment. The structural rearrangement of proteins that occurred with the hydrothermal treatment most likely promoted the capacity of proteins to bind to aglycone. Moreover, the structure shape and size of soy protein isolates verified by scanning electron microscopy appears to be related to the formation of hydrophobic surfaces and hydrophobic zones at 40 °C and 60 °C, respectively, affecting the protein digestibility, WAC, and FC of soy protein isolates. The aglycone content in the soy protein isolate can be improved with the hydrothermal treatment of soybeans. The temperature and time used for hydrothermal treatment must be selected in order to achieve a soy protein isolate with high aglycone content, extraction yield, and functionality. This technology is suitable for providing healthier soy protein isolates for food industry with improved functional and structural properties. © 2014 Institute of Food Technologists®

  1. Flavonoids from the flowers of Nymphaea alba L.

    Directory of Open Access Journals (Sweden)

    Jerzy Jambor

    2014-01-01

    Full Text Available Ten flavonoids were obtained from the flowers of Nymphaea alba L. Their structures were determined mainly on the basis of spectral analyses (UV, 'H NMR, MS. The following aglycons were isolated: quercetin, kaempferol, isokaempferide and apigenin as well as the following glycosides: quercetion 4'-β-xyloside, 3-methylquercetin 3'-β-xyloside and a mixture of quercetin 3-galactoside and 3-glucoside. The structures of three compounds obtained in very small amounts were determined in part.

  2. Fate in Soil of Flavonoids Released from White Clover (Trifolium repens L.)

    DEFF Research Database (Denmark)

    Carlsen, Sandra C. K.; Pedersen, Hans A.; Spliid, Niels H.

    2012-01-01

    flavonoid aglycones were formononetin, medicarpin, and kaempferol. Soil-incorporated white clover plants generated high concentrations of the glycosides kaempferol-Rha-Xyl-Gal and quercetin-Xyl-Gal. Substantial amounts of kaempferol persisted in the soil for days while the other compounds were degraded...

  3. Inhibitory effects of flavonoids on biofilm formation by Staphylococcus aureus that overexpresses efflux protein genes.

    Science.gov (United States)

    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.

  4. Optimization of Extraction Conditions for Maximal Phenolic, Flavonoid and Antioxidant Activity from Melaleuca bracteata Leaves Using the Response Surface Methodology.

    Directory of Open Access Journals (Sweden)

    Wencheng Hou

    Full Text Available Melaleuca bracteata is a yellow-leaved tree belonging to the Melaleuca genus. Species from this genus are known to be good sources of natural antioxidants, for example, the "tea tree oil" derived from M. alternifolia is used in food processing to extend the shelf life of products. In order to determine whether M. bracteata contains novel natural antioxidants, the components of M. bracteata ethanol extracts were analyzed by gas chromatography-mass spectrometry. Total phenolic and flavonoid contents were extracted and the antioxidant activities of the extracts evaluated. Single-factor experiments, central composite rotatable design (CCRD and response surface methodology (RSM were used to optimize the extraction conditions for total phenolic content (TPC and total flavonoid content (TFC. Ferric reducing power (FRP and 1,1-Diphenyl-2-picrylhydrazyl radical (DPPH· scavenging capacity were used as the evaluation indices of antioxidant activity. The results showed that the main components of M. bracteata ethanol extracts are methyl eugenol (86.86% and trans-cinnamic acid methyl ester (6.41%. The single-factor experiments revealed that the ethanol concentration is the key factor determining the TPC, TFC, FRP and DPPH·scavenging capacity. RSM results indicated that the optimal condition of all four evaluation indices was achieved by extracting for 3.65 days at 53.26°C in 34.81% ethanol. Under these conditions, the TPC, TFC, FRP and DPPH·scavenging capacity reached values of 88.6 ± 1.3 mg GAE/g DW, 19.4 ± 0.2 mg RE/g DW, 2.37 ± 0.01 mM Fe2+/g DW and 86.0 ± 0.3%, respectively, which were higher than those of the positive control, methyl eugenol (FRP 0.97 ± 0.02 mM, DPPH·scavenging capacity 58.6 ± 0.7% at comparable concentrations. Therefore, the extracts of M. bracteata leaves have higher antioxidant activity, which did not only attributed to the methyl eugenol. Further research could lead to the development of a potent new natural antioxidant.

  5. Inhibition of Taq DNA polymerase by iridoid aglycone derivates.

    Science.gov (United States)

    Pungitore, C R; García, C; Sotero Martín, V; Tonn, C E

    2012-11-08

    Faithful replication of DNA molecules by DNA polymerases is essential for genome integrity and correct transmission of genetic information in all living organisms. DNA polymerases have recently emerged as important cellular targets for chemical intervention in the development of anti--cancer agents. Herein we report additional synthesis of simplified bicyclic aglycones of iridoids and their biological activity against Taq DNA polymerase with the object to find out some of the likely molecular targets implicated in the biological activity showed for this kind of compounds. The compounds 14, 33 and 34 showed inhibitory activity against Taq DNA polymerase with IC(50) values of 13.47, 17.65 and 18.31 μM, respectively. These results would allow proposing to DNA polymerases as the molecular targets implicated in this bioactivity and enhance the iridoid aglycones as leader molecule to develop new drugs for cancer therapy.

  6. Isorhamnetin, A Flavonol Aglycone from Ginkgo biloba L., Induces Neuronal Differentiation of Cultured PC12 Cells: Potentiating the Effect of Nerve Growth Factor

    Directory of Open Access Journals (Sweden)

    Sherry L. Xu

    2012-01-01

    Full Text Available Flavonoids, a group of compounds mainly derived from vegetables and herbal medicines, share a chemical resemblance to estrogen, and indeed some of which have been used as estrogen substitutes. In searching for possible functions of flavonoids, the neuroprotective effect in brain could lead to novel treatment, or prevention, for neurodegenerative diseases. Here, different subclasses of flavonoids were analyzed for its inductive role in neurite outgrowth of cultured PC12 cells. Amongst the tested flavonoids, a flavonol aglycone, isorhamnetin that was isolated mainly from the leaves of Ginkgo biloba L. showed robust induction in the expression of neurofilament, a protein marker for neurite outgrowth, of cultured PC12 cells. Although isorhamnetin by itself did not show significant inductive effect on neurite outgrowth of cultured PC12 cells, the application of isorhamnetin potentiated the nerve growth factor- (NGF-induced neurite outgrowth. In parallel, the expression of neurofilaments was markedly increased in the cotreatment of NGF and isorhamnetin in the cultures. The identification of these neurite-promoting flavonoids could be very useful in finding potential drugs, or food supplements, for treating various neurodegenerative diseases, including Alzheimer’s disease and depression.

  7. Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes

    DEFF Research Database (Denmark)

    Justesen, U.; Knuthsen, Pia

    2001-01-01

    Many herbs are known as excellent sources of natural antioxidants, and consumption of fresh herbs in the diet may therefore contribute to the daily antioxidant intake. The present study was performed in order to quantify flavonoids in commonly eaten fresh herbs. Fifteen fresh herbs (basil, chives......, coriander, cress, dill, lemon balm, lovage, oregano, parsley, rosemary, sage, spearmint, tarragon, thyme, and watercress) were analysed by HPLC and mass spectrometry. Five major flavonoid aglycones were detected and quantified by HPLC after acid hydrolysis: apigenin, isorhamnetin, kaempferol, luteolin......, and quercetin. The highest levels of flavonoids were found in parsley (510-630 mg apigenin /100 g), lovage (170 mg quercetin/100g), mint (18-100 mg apigenin/ 100 g), and dill (48-110 mg quercetin/100 g). Mass spectrometric detection, using atmospheric pressure chemical ionisation (APCI), was used to verify...

  8. Total synthesis of putative 11-epi-lyngbouilloside aglycon

    Directory of Open Access Journals (Sweden)

    Amandine Kolleth

    2016-08-01

    Full Text Available We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the natural product and irrevocably confirm its structure.

  9. Bioavailability of the flavonol quercetin in neonatal calves after oral administration of quercetin aglycone or rutin.

    Science.gov (United States)

    Maciej, J; Schäff, C T; Kanitz, E; Tuchscherer, A; Bruckmaier, R M; Wolffram, S; Hammon, H M

    2015-06-01

    Polyphenols, such as flavonoids, are secondary plant metabolites with potentially health-promoting properties. In newborn calves flavonoids may improve health status, but little is known about the systemically availability of flavonoids in calves to exert biological effects. The aim of this study was to investigate the oral bioavailability of the flavonol quercetin, applied either as quercetin aglycone (QA) or as its glucorhamnoside rutin (RU), in newborn dairy calves. Twenty-one male newborn German Holstein calves were fed equal amounts of colostrum and milk replacer according to body weight. On d 2 and 29 of life, 9 mg of quercetin equivalents/kg of body weight, either fed as QA or as RU, or no quercetin (control group) were fed together with the morning meal. Blood samples were taken before and 0.5, 1, 1.5, 2, 2.5, 3, 4, 5, 6, 12, 24, and 48 h after feed intake. Quercetin and quercetin metabolites with an intact flavonol structure (isorhamnetin, tamarixetin, and kaempferol) were analyzed in blood plasma after treatment with glucuronidase or sulfatase by HPLC with fluorescence detection. Maximum individual plasma concentration was depicted from the concentration-time-curve on d 2 and 29, respectively. Additional blood samples were taken to measure basal plasma concentrations of total protein, albumin, urea, and lactate as well as pre- and postprandial plasma concentrations of glucose, nonesterified fatty acids, insulin, and cortisol. Plasma concentrations of quercetin and its metabolites were significantly higher on d 2 than on d 29 of life, and administration of QA resulted in higher plasma concentrations of quercetin and its metabolites than RU. The relative bioavailability of total flavonols (sum of quercetin and its metabolites isorhamnetin, tamarixetin, and kaempferol) from RU was 72.5% on d 2 and 49.6% on d 29 when compared with QA (100%). Calves fed QA reached maximum plasma concentrations of total flavonols much earlier than did RU-fed calves. Plasma

  10. Foliar flavonoids from Tanacetum vulgare var. boreale and their geographical variation.

    Science.gov (United States)

    Uehara, Ayumi; Akiyama, Shinobu; Iwashina, Tsukasa

    2015-03-01

    Foliar flavonoids of Tanacetum vulgare var. boreale were isolated. Eight flavonoid glycosides, 7-O-glucosides of apigenin, luteolin, scutellarein and 6- hydroxyluteolin, and 7-O-glucuronides of apigenin, luteolin, chrysoeriol and eriodictyol were identified. Moreover, eight flavonoid aglycones, apigenin, luteolin, hispidulin, nepetin, eupatilin, jaceosidin, pectolinarigenin and axillarin were also isolated and identified. The flavonoid composition of two varieties of T. vulgare, i.e. var. boreale and var. vulgare, were compared. All samples of var. boreale and one sample of var. vulgare had the same flavonoid pattern, and could be distinguished from almost all the samples of var. vulgare. Thus, the occurrence of chemotypes, which are characterized by either the presence or absence of scutellarein 7-O-glucoside, eriodictyol 7-O-glucuronide and pectolinarigenin was shown in T. vulgare sensu lato.

  11. Flavonoids Are Inhibitors of Human Organic Anion Transporter 1 (OAT1)–Mediated Transport

    Science.gov (United States)

    An, Guohua; Wang, Xiaodong

    2014-01-01

    Organic anion transporter 1 (OAT1) has been reported to be involved in the nephrotoxicity of many anionic xenobiotics. As current clinically used OAT1 inhibitors are often associated with safety issues, identifying potent OAT1 inhibitors with little toxicity is of great value in reducing OAT1-mediated drug nephrotoxicity. Flavonoids are a class of polyphenolic compounds with exceptional safety records. Our objective was to evaluate the effects of 18 naturally occurring flavonoids, and some of their glycosides, on the uptake of para-aminohippuric acid (PAH) in both OAT1-expressing and OAT1-negative LLC-PK1 cells. Most flavonoid aglycones produced substantial decreases in PAH uptake in OAT1-expressing cells. Among the flavonoids screened, fisetin, luteolin, morin, and quercetin exhibited the strongest effect and produced complete inhibition of OAT1-mediated PAH uptake at a concentration of 50 μM. Further concentration-dependent studies revealed that both morin and luteolin are potent OAT1 inhibitors, with IC50 values of flavonoid aglycones, all flavonoid glycosides had negligible or small effects on OAT1. In addition, the role of OAT1 in the uptake of fisetin, luteolin, morin, and quercetin was investigated and fisetin was found to be a substrate of OAT1. Taken together, our results indicate that flavonoids are a novel class of OAT1 modulators. Considering the high consumption of flavonoids in the diet and in herbal products, OAT1-mediated flavonoid-drug interactions may be clinically relevant. Further investigation is warranted to evaluate the nephroprotective role of flavonoids in relation to drug-induced nephrotoxicity mediated by the OAT1 pathway. PMID:25002746

  12. Flavonoids and coumarins from Hieracium pilosella L. (Asteraceae

    Directory of Open Access Journals (Sweden)

    Tadeusz Krzaczek

    2011-01-01

    Full Text Available Typical chromatographic methods were successfully applied to isolate nine flavonoid compounds and two coumarin glycosides from the inflorescences and the herb of Hieracium pilosella L. Repeated column chromatography, occasionally paper chromatography and recrystallization made the separation of three flavonoid aglycones and six glycosides - possible. Coumarin glycosides were isolated by preparative thin layer chromatography. Subsequent UV, NMR and MS analyses have led to identification of the following flavonoid derivatives: known for the species - apigenin, luteolin, luteolin 7-O- ß-glucopyranoside, luteolin 4’-O-ß-glucopyranoside, isoetin 7-O-ß- -glucopyranoside, isoetin 4’-O-ß-glucuronide and new for the species – kaempferol 3-methyl ether and apigenin 7-O-ß-glucopyranoside. Third isoetin glycoside contained two different sugar moieties: xylose and glucose, probably attached to the hydroxyl groups at C-4’ or C-4’ and C-2’(or 5’ of an aglycone. Umbelliferone 7-O-ß-glucopyranoside (skimmin and new for the genus Hieracium esculetin 7-O-ß-glucopyranoside (cichoriin were determined by NMR and MS methods.

  13. Seasonal variation of flavonoids in Teucrium polium L. (Lamiaceae

    Directory of Open Access Journals (Sweden)

    Gjoshe Stefkov

    2009-02-01

    Full Text Available Тhe aim of the present study was identification of flavone aglycones and determination of the content of each and the content of total flavonoids as well as investigation of the eventual seasonal variations of flavonoids in Teucrium polium L. (Lamiaceae. The plant samples were collected at six different locations in Republic of Macedonia, during summer in 1999, 2000 and 2003. For determination of seasonal variations, the samples were collected in v. Koleshino, in 2004, each month during the whole season. Six flavone aglycones (luteolin, apigenin, diosmetin, cirsiliol, cirsimaritin and cirsilineol were identified in the hydrolyzed extracts of the over ground part of Teucrium polium by HPLC method. The most abundant flavone was luteolin, followed by apigenin and cirsimaritin. Great seasonal variations were found in the content of each and in the content of total amount of flavonoids. The most abundant flavone during the whole season was luteolin with the highest content in May. The content of total flavonids was the highest in the period from May to July, which could be recommended as the most convenience period in the season for collecting of the plant material from Teucrium polium.

  14. 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...

  15. Identification and quantification of flavonoids in human urine samples by column switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry

    DEFF Research Database (Denmark)

    Nielsen, S. E.; Freese, R.; Cornett, Claus

    2000-01-01

    A rapid and sensitive high-performance liquid chromatographic mass spectrometric (HPLC-MS) method is described for the determination and quantification of 12 dietary flavonoid glycosides and aglycons in human urine samples. Chromatographic separation of the analytes of interest was achieved by co...

  16. Flavonoids and fatty acids of Camellia japonica leaves extract

    Directory of Open Access Journals (Sweden)

    Cinthia M. Azuma

    2011-07-01

    Full Text Available The ethanol extract from the leaves of Camellia japonica L., Theaceae, showed antiradical potential in the DPPH test using TLC plates (SiO2. Aiming the isolation of active compounds, this extract was partitioned between BuOH:H2O (1:1 and the two obtained phases were also evaluated to detection of antiradical activity. The active BuOH phase was fractionated in Sephadex LH-20 and silica (normal or reverse phase to afford three aglycone flavonoids (quercetin, kaempferol and apigenin, which have been described in the C. japonica at first time, two glycosilated flavonoids (rutin and quercetrin, and a mixture of saturated fatty acids. The structures of isolated compounds were defined by NMR and GC/MS analyses.

  17. Flavonoids and fatty acids of Camellia japonica leaves extract

    Directory of Open Access Journals (Sweden)

    Cinthia M. Azuma

    2011-12-01

    Full Text Available The ethanol extract from the leaves of Camellia japonica L., Theaceae, showed antiradical potential in the DPPH test using TLC plates (SiO2. Aiming the isolation of active compounds, this extract was partitioned between BuOH:H2O (1:1 and the two obtained phases were also evaluated to detection of antiradical activity. The active BuOH phase was fractionated in Sephadex LH-20 and silica (normal or reverse phase to afford three aglycone flavonoids (quercetin, kaempferol and apigenin, which have been described in the C. japonica at first time, two glycosilated flavonoids (rutin and quercetrin, and a mixture of saturated fatty acids. The structures of isolated compounds were defined by NMR and GC/MS analyses.

  18. Antioxidative properties of flavonoids

    NARCIS (Netherlands)

    Bowedes, T.C.F.; Luttikhold, J.; Stijn, van M.F.M.; Visser, M.; Norren, van K.; Vermeulen, M.A.R.; Leeuwen, P.A.M.

    2011-01-01

    Evidence accumulates that a family of plant compounds, known as flavonoids, can prevent or slow down the progression of cardiovascular diseases, cancer, inflammatory and neurodegenerative diseases. Flavonoids are considered beneficial, this is often attributed to their powerful antioxidant

  19. Optimization of Aqueous Extraction from Kalanchoe pinnata Leaves to Obtain the Highest Content of an Anti-inflammatory Flavonoid using a Response Surface Model.

    Science.gov (United States)

    Dos Santos Nascimento, Luana Beatriz; de Aguiar, Paula Fernandes; Leal-Costa, Marcos Vinicius; Coutinho, Marcela Araújo Soares; Borsodi, Maria Paula Gonçalves; Rossi-Bergmann, Bartira; Tavares, Eliana Schwartz; Costa, Sônia Soares

    2018-05-01

    The medicinal plant Kalanchoe pinnata is a phenolic-rich species used worldwide. The reports on its pharmacological uses have increased by 70% in the last 10 years. The leaves of this plant are the main source of an unusual quercetin-diglycosyl flavonoid (QAR, quercetin arabinopyranosyl rhamnopyranoside), which can be easily extracted using water. QAR possess a strong in vivo anti-inflammatory activity. To optimize the aqueous extraction of QAR from K. pinnata leaves using a three-level full factorial design. After a previous screening design, time (x 1 ) and temperature (x 2 ) were chosen as the two independent variables for optimization. Freeze-dried leaves were extracted with water (20% w/v), at 30°C, 40°C or 50°C for 5, 18 or 30 min. QAR content (determined by HPLC-DAD) and yield of extracts were analyzed. The optimized extracts were also evaluated for cytotoxicity. The optimal heating times for extract yield and QAR content were similar in two-dimensional (2D) surface responses (between 12.8 and 30 min), but their optimal extraction temperatures were ranged between 40°C and 50°C for QAR content and 30°C and 38°C for extract yield. A compromise region for both parameters was at the mean points that were 40°C for the extraction temperature and 18 min for the total time. The optimized process is faster and spends less energy than the previous one (water; 30 min at 55°C); therefore is greener and more attractive for industrial purposes. This is the first report of extraction optimization of this bioactive flavonoid. Copyright © 2018 John Wiley & Sons, Ltd. Copyright © 2018 John Wiley & Sons, Ltd.

  20. Photochemistry of Flavonoids

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    Jan H. Van der Westhuizen

    2010-08-01

    Full Text Available Flavonoids and their photochemical transformations play an important role in biological processes in nature. Synthetic photochemistry allows access to molecules that cannot be obtained via more conventional methods. This review covers all published synthetic photochemical transformations of the different classes of flavonoids. It is first comprehensive review on the photochemistry of flavonoids.

  1. A,B-indolosteroids. XIII. New modification of the steroid aglycone of solasodine

    International Nuclear Information System (INIS)

    Gutnik, S.B.; Shner, V.F.; Kuleshova, L.N.; Suvorov, N.N.

    1986-01-01

    A new modification of the steroid skeleton of the solasodine aglycone was realized; compounds of the A-nor-3-azaspirosolane series with an unsubstituted position 28 were obtained. The properties of the synthesized heterocyclic analogs of solasodine were studied

  2. Comparison of flavonoid profiles of cultivated plants of Achillea asplenifolia, Achillea collina and cultivar ”Proa”

    Directory of Open Access Journals (Sweden)

    Nikolova, M.

    2013-12-01

    Full Text Available Flavonoid aglycone profiles of cultivated plants of Achillea collina, A. asplenifolia and cultivar "Proa" presented with different origins were compared. The evaluation was undertaken to determine intraspecific variability of flavonoid profiles when the plants are grown in the uniform conditions. Eight flavonoid aglycones were detected by thin layer chromatography and comparison with known compounds. Highly methylated quercetagetin derivatives predominate in the exudates. The flavonoid profiles of A. colina consist mainly of quercetagetin 3,6,4'-trimethyl ether (centaureidin, 6-hydroxykaempferol 3,6,4'-trimethyl ether and quercetagetin 3,6,7,4'-tetramethyl ether (casticin while the profiles of A. asplenifolia of quercetagetin 3,6,7,3',4'-pentamethyl ether (artemetin, casticin and scutellarein 6,4'-dimethyl ether. In the profiles of A. asplenifolia quercetagetin 3,6,4'-trimethyl ether was not found in the extracts of one of the two origins. The extracts of cultivar exhibited a less diversified flavonoid profile with main component centaureidin. No significant difference was found in the flavonoid profiles of the extracts of the both origins of the cultivar “Proa” and A. collina.

  3. Fruit-Surface Flavonoid Accumulation in Tomato Is Controlled by a SlMYB12-Regulated Transcriptional Network

    NARCIS (Netherlands)

    Adato, A.; Mandel, T.; Mintz-Orion, S.; Venger, I.; Levy, D.; Yativ, M.; Dominguez, E.; Wang, Z.; Vos, de C.H.; Jetter, R.; Schreiber, L.; Heredia, A.; Rogachev, I.; Aharoni, A.

    2009-01-01

    The cuticle covering plants' aerial surfaces is a unique structure that plays a key role in organ development and protection against diverse stress conditions. A detailed analysis of the tomato colorless-peel y mutant was carried out in the framework of studying the outer surface of reproductive

  4. The antileishmanial activity assessment of unusual flavonoids from Kalanchoe pinnata.

    Science.gov (United States)

    Muzitano, Michelle F; Tinoco, Luzineide W; Guette, Catherine; Kaiser, Carlos R; Rossi-Bergmann, Bartira; Costa, Sônia S

    2006-09-01

    The importance of flavonoids for the antileishmanial activity of Kalanchoe pinnata was previously demonstrated by the isolation of quercitrin, a potent antileishmanial flavonoid. In the present study, the aqueous leaf extract from the medicinal plant K. pinnata (Crassulaceae) afforded a kaempferol di-glycoside, named kapinnatoside, identified as kaempferol 3-O-alpha-L-arabinopyranosyl (1-->2) alpha-L-rhamnopyranoside (1). In addition, two unusual flavonol and flavone glycosides already reported, quercetin 3-O-alpha-L-arabinopyranosyl (1-->2) alpha-L-rhamnopyranoside (2) and 4',5-dihydroxy-3',8-dimethoxyflavone 7-O-beta-D-glucopyranoside (3), have been isolated. Their structures were determined via analyses of mono and bi-dimensional (1)H and (13)C NMR spectroscopic experiments and HR-MALDI mass spectra. Because of its restricted occurrence and its abundance in K. pinnata, flavonoid (2) may be a chemical marker for this plant species of high therapeutic potential. The three flavonoids were tested separately against Leishmania amazonenis amastigotes in comparison with quercitrin, quercetin and afzelin. The quercetin aglycone - type structure, as well as a rhamnosyl unit linked at C-3, seem to be important for antileishmanial activity.

  5. Antioxidant properties of flavonoids

    Directory of Open Access Journals (Sweden)

    Sofna D.S. Banjarnahor

    2015-01-01

    Full Text Available Flavonoids represent a remarkable group of plant secondary metabolites and have long been used as traditional medicines with scientifically proven pharmacological benefits. They serve vast-ranging medicinal activities that may lead drug discovery with novel and potential therapeutic evidence. Latest research magnifies primarily functional activity of flavonoids as antioxidant against oxidative stress. This review enlightens the prospective role of flavonoids as antioxidant.

  6. Flavonoids Released Naturally from Alfalfa Seeds Enhance Growth Rate of Rhizobium meliloti1

    Science.gov (United States)

    Hartwig, Ueli A.; Joseph, Cecillia M.; Phillips, Donald A.

    1991-01-01

    Alfalfa (Medicago sativa L.) releases different flavonoids from seeds and roots. Imbibing seeds discharge 3′,4′,5,7-substituted flavonoids; roots exude 5-deoxy molecules. Many, but not all, of these flavonoids induce nodulation (nod) genes in Rhizobium meliloti. The dominant flavonoid released from alfalfa seeds is identified here as quercetin-3-O-galactoside, a molecule that does not induce nod genes. Low concentrations (1-10 micromolar) of this compound, as well as luteolin-7-O-glucoside, another major flavonoid released from germinating seeds, and the aglycones, quercetin and luteolin, increase growth rate of R. meliloti in a defined minimal medium. Tests show that the 5,7-dihydroxyl substitution pattern on those molecules was primarily responsible for the growth effect, thus explaining how 5-deoxy flavonoids in root exudates fail to enhance growth of R. meliloti. Luteolin increases growth by a mechanism separate from its capacity to induce rhizobial nod genes, because it still enhanced growth rate of R. meliloti lacking functional copies of the three known nodD genes. Quercetin and luteolin also increased growth rate of Pseudomonas putida. They had no effect on growth rate of Bacillus subtilis or Agrobacterium tumefaciens, but they slowed growth of two fungal pathogens of alfalfa. These results suggest that alfalfa can create ecochemical zones for controlling soil microbes by releasing structurally different flavonoids from seeds and roots. PMID:16668056

  7. Concurrent Synthesis and Release of nod-Gene-Inducing Flavonoids from Alfalfa Roots 1

    Science.gov (United States)

    Maxwell, Carl A.; Phillips, Donald A.

    1990-01-01

    Flavonoid signals from alfalfa (Medicago sativa L.) induce transcription of nodulation (nod) genes in Rhizobium meliloti. Alfalfa roots release three major nod-gene inducers: 4′,7-dihydroxyflavanone, 4′,7-dihydroxyflavone, and 4,4′-dihydroxy-2′-methoxychalcone. The objective of the present study was to define temporal relationships between synthesis and exudation for those flavonoids. Requirements for concurrent flavonoid biosynthesis were assessed by treating roots of intact alfalfa seedlings with [U-14C]-l-phenylalanine in the presence or absence of the phenylalanine ammonia-lyase inhibitor l-2-aminoxy-3-phenylpropionic acid (AOPP). In the absence of AOPP, each of the three flavonoids in exudates contained 14C. In the presence of AOPP, 14C labeling and release of all the exuded nod-gene inducers were reduced significantly. AOPP inhibited labeling and release of the strongest nod-gene inducer, methoxychalcone, by more than 90%. Experiments with excised cotyledons, hypocotyls, and roots incubated in solution showed that the flavonoids could be synthesized in and released from each organ. However, the ratio of the three flavonoids in exudates from intact plants was most similar to the ratio recently synthesized and released from excised roots. A portion of recently synthesized flavonoid aglycones was found conjugated, presumably as glycosides, in root extracts and may have been involved in the release process. Data from root extracts showed that formononetin, an isoflavonoid which does not induce nod genes, was present in conjugated and aglycone forms but was not released by normal intact roots. In contrast, roots stressed with CuCl2 did release the aglycone formononetin. Thus, the release process responsible for exudation of nod-gene inducers appears to be specific rather than a general phenomenon such as a sloughing off of cells during root growth. The synthesis and specific concurrent release of flavonoid nod-gene inducers in this study is consistent with

  8. Genome-Wide Identification and Functional Characterization of UDP-Glucosyltransferase Genes Involved in Flavonoid Biosynthesis in Glycine max.

    Science.gov (United States)

    Yin, Qinggang; Shen, Guoan; Di, Shaokang; Fan, Cunying; Chang, Zhenzhan; Pang, Yongzhen

    2017-09-01

    Flavonoids, natural products abundant in the model legume Glycine max, confer benefits to plants and to animal health. Flavonoids are present in soybean mainly as glycoconjugates. However, the mechanisms of biosynthesis of flavonoid glycosides are largely unknown in G. max. In the present study, 212 putative UDP-glycosyltransferase (UGT) genes were identified in G. max by genome-wide searching. The GmUGT genes were distributed differentially among the 20 chromosomes, and they were expressed in various tissues with distinct expression profiles. We further analyzed the enzymatic activities of 11 GmUGTs that are potentially involved in flavonoid glycosylation, and found that six of them (UGT72X4, UGT72Z3, UGT73C20, UGT88A13, UGT88E19 and UGT92G4) exhibited activity toward flavonol, isoflavone, flavone and flavanol aglycones with different kinetic properties. Among them, UGT72X4, UGT72Z3 and UGT92G4 are flavonol-specific UGTs, and UGT73C20 and UGT88E19 exhibited activity toward both flavonol and isoflavone aglycones. In particular, UGT88A13 exhibited activity toward epicatechin, but not for the flavonol aglycones kaempferol and quercetin. Overexpression of these six GmUGT genes significantly increased the contents of isoflavone and flavonol glucosides in soybean hairy roots. In addition, overexpression of these six GmUGT genes also affected flavonol glycoside contents differently in seedlings and seeds of transgenic Arabidopsis thaliana. We provide valuable information on the identification of all UGT genes in soybean, and candidate GmUGT genes for potential metabolic engineering of flavonoid compounds in both Escherichia coli and plants. © The Author 2017. Published by Oxford University Press on behalf of Japanese Society of Plant Physiologists. All rights reserved. For permissions, please email: journals.permissions@oup.com.

  9. Urinary metabolite profiling of flavonoids in Chinese volunteers after consumption of orange juice by UFLC-Q-TOF-MS/MS.

    Science.gov (United States)

    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.

  10. One-Step Extraction and Hydrolysis of Flavonoid Glycosides in Rape Bee Pollen Based on Soxhlet-Assisted Matrix Solid Phase Dispersion.

    Science.gov (United States)

    Tu, Xijuan; Ma, Shuangqin; Gao, Zhaosheng; Wang, Jing; Huang, Shaokang; Chen, Wenbin

    2017-11-01

    Flavonoids are frequently found as glycosylated derivatives in plant materials. To determine contents of flavonoid aglycones in these matrices, procedures for the extraction and hydrolysis of flavonoid glycosides are required. The current sample preparation method is both labour and time consuming. Develop a modified matrix solid phase dispersion (MSPD) procedure as an alternative methodology for the one-step extraction and hydrolysis of flavonoid glycosides. HPLC-DAD was applied for demonstrating the one-step extraction and hydrolysis of flavonoids in rape bee pollen. The obtained contents of flavonoid aglycones (quercetin, kaempferol, isorhamnetin) were used for the optimisation and validation of the method. The extraction and hydrolysis were accomplished in one step. The procedure completes in 2 h with silica gel as dispersant, a 1:2 ratio of sample to dispersant, and 60% aqueous ethanol with 0.3 M hydrochloric acid as the extraction solution. The relative standard deviations (RSDs) of repeatability were less than 5%, and the recoveries at two fortified levels were between 88.3 and 104.8%. The proposed methodology is simple and highly efficient, with good repeatability and recovery. Compared with currently available methods, the present work has advantages of using less time and labour, higher extraction efficiency, and less consumption of the acid catalyst. This method may have applications for the one-step extraction and hydrolysis of bioactive compounds from plant materials. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  11. Mechanism of Isoflavone Aglycone's Effect on Cognitive Performance of Senescence-Accelerated Mice

    Science.gov (United States)

    Yang, Hong; Jin, Guifang; Ren, Dongdong; Luo, Sijing; Zhou, Tianhong

    2011-01-01

    This study investigated the effect of isoflavone aglycone (IA) on the learning and memory performance of senescence-accelerated mice, and explored its neural protective mechanism. Results showed that SAM-P/8 senescence-accelerated mice treated with IA performed significantly better in the Y-maze cognitive test than the no treatment control (P less…

  12. Recent patents on flavonoids.

    Science.gov (United States)

    Mamta, Gokhale; Bansal, Y K; Sandhu, S S

    2013-12-01

    Flavonoids are substances which are widely distributed in the plant kingdom. They occur in considerable quantities in common food products, spices and beverages. Interest of researchers has been greatly enhanced towards therapeutic potential of flavonoids in last some years. This review summarizes important patents pertaining to recent biotechnological techniques applied for the production, analysis of biosynthetic pathways, effects and applications of different flavonoids. For systematic studies investigations which have been published in the form of patents, are classified in different sectors like biosynthesis, medical application, antimicrobial activity, alteration of flower color, industrial application, cosmetics, food and plant tissue culture. A number of activities have been observed in each sector with vast area of research on flavonoids.

  13. Flavonoids from Chenopodium botrys.

    Science.gov (United States)

    de Pascual-T, J; González, M S; Vicente, S; Bellido, I S

    1981-04-01

    From Chenopodium botrys, five flavonoids have been isolated: hispidulin, 1, salvigenin 2, 5-methylsalvigenin, 3, 7-methyleupatulin, 4 and sinensetin, 5. None of them have been previously reported from Ch. botrys.

  14. Novel Benzoxazine-Based Aglycones Block Glucose Uptake In Vivo by Inhibiting Glycosidases

    Science.gov (United States)

    Jagadish, Swamy; Paricharak, Shardul; Hemshekhar, Mahadevappa; Mason, Daniel; Kemparaju, Kempaiah; Girish, Kesturu S.; Basappa; Bender, Andreas; Rangappa, Kanchugarakoppal S.

    2014-01-01

    Glycoside hydrolases catalyze the selective hydrolysis of glycosidic bonds in oligosaccharides, polysaccharides, and their conjugates. β-glucosidases occur in all domains of living organisms and constitute a major group among glycoside hydrolases. On the other hand, the benzoxazinoids occur in living systems and act as stable β-glucosides, such as 2-(2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)-β-D-gluco-pyranose, which hydrolyse to an aglycone DIMBOA. Here, we synthesized the library of novel 1,3-benzoxazine scaffold based aglycones by using 2-aminobenzyl alcohols and aldehydes from one-pot reaction in a chloroacetic acid catalytic system via aerobic oxidative synthesis. Among the synthesized benzoxazines, 4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol (compound 7) exhibit significant inhibition towards glucosidase compared to acarbose, with a IC50 value of 11.5 µM. Based upon results generated by in silico target prediction algorithms (Naïve Bayesian classifier), these aglycones potentially target the additional sodium/glucose cotransporter 1 (where a log likelihood score of 2.70 was observed). Furthermore, the in vitro glucosidase activity was correlated with the in silico docking results, with a high docking score for the aglycones towards the substrate binding site of glycosidase. Evidently, the in vitro and in vivo experiments clearly suggest an anti-hyperglycemic effect via glucose uptake inhibition by 4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)phenol in the starved rat model. These synthetic aglycones could constitute a novel pharmacological approach for the treatment, or re-enforcement of existing treatments, of type 2 diabetes and associated secondary complications. PMID:25047583

  15. Novel benzoxazine-based aglycones block glucose uptake in vivo by inhibiting glycosidases.

    Directory of Open Access Journals (Sweden)

    Hanumantharayappa Bharathkumar

    Full Text Available Glycoside hydrolases catalyze the selective hydrolysis of glycosidic bonds in oligosaccharides, polysaccharides, and their conjugates. β-glucosidases occur in all domains of living organisms and constitute a major group among glycoside hydrolases. On the other hand, the benzoxazinoids occur in living systems and act as stable β-glucosides, such as 2-(2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H-one-β-D-gluco-pyranose, which hydrolyse to an aglycone DIMBOA. Here, we synthesized the library of novel 1,3-benzoxazine scaffold based aglycones by using 2-aminobenzyl alcohols and aldehydes from one-pot reaction in a chloroacetic acid catalytic system via aerobic oxidative synthesis. Among the synthesized benzoxazines, 4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-ylphenol (compound 7 exhibit significant inhibition towards glucosidase compared to acarbose, with a IC50 value of 11.5 µM. Based upon results generated by in silico target prediction algorithms (Naïve Bayesian classifier, these aglycones potentially target the additional sodium/glucose cotransporter 1 (where a log likelihood score of 2.70 was observed. Furthermore, the in vitro glucosidase activity was correlated with the in silico docking results, with a high docking score for the aglycones towards the substrate binding site of glycosidase. Evidently, the in vitro and in vivo experiments clearly suggest an anti-hyperglycemic effect via glucose uptake inhibition by 4-(7-chloro-2,4-dihydro-1H-benzo[d][1,3]oxazin-2-ylphenol in the starved rat model. These synthetic aglycones could constitute a novel pharmacological approach for the treatment, or re-enforcement of existing treatments, of type 2 diabetes and associated secondary complications.

  16. The polyphenol oleuropein aglycone protects TgCRND8 mice against Aß plaque pathology.

    Directory of Open Access Journals (Sweden)

    Cristina Grossi

    Full Text Available The claimed beneficial effects of the Mediterranean diet include prevention of several age-related dysfunctions including neurodegenerative diseases and Alzheimer-like pathology. These effects have been related to the protection against cognitive decline associated with aging and disease by a number of polyphenols found in red wine and extra virgin olive oil. The double transgenic TgCRND8 mice (overexpressing the Swedish and Indiana mutations in the human amyloid precursor protein, aged 1.5 and 4, and age-matched wild type control mice were used to examine in vivo the effects of 8 weeks dietary supplementation of oleuropein aglycone (50 mg/kg of diet, the main polyphenol found in extra virgin olive oil. We report here that dietary supplementation of oleuropein aglycone strongly improves the cognitive performance of young/middle-aged TgCRND8 mice, a model of amyloid-ß deposition, respect to age-matched littermates with un-supplemented diet. Immunofluorescence analysis of cerebral tissue in oleuropein aglycone-fed transgenic mice showed remarkably reduced ß-amyloid levels and plaque deposits, which appeared less compact and "fluffy"; moreover, microglia migration to the plaques for phagocytosis and a remarkable reduction of the astrocyte reaction were evident. Finally, oleuropein aglycone-fed mice brain displayed an astonishingly intense autophagic reaction, as shown by the increase of autophagic markers expression and of lysosomal activity. Data obtained with cultured cells confirmed the latter evidence, suggesting mTOR regulation by oleuropein aglycone. Our results support, and provide mechanistic insights into, the beneficial effects against Alzheimer-associated neurodegeneration of a polyphenol enriched in the extra virgin olive oil, a major component of the Mediterranean diet.

  17. Ultrasonic-Assisted Extraction and Antioxidant Activity of Flavonoids ...

    African Journals Online (AJOL)

    Purpose: To identify the main flavonoid in Adinandra nitida leaf, employ response surface methodology to optimize its ultrasonic-assisted extraction, and determine the antioxidant activity of the obtained extract. Methods: The main flavonoid in Adinandra nitida leaf was obtained by traditional solvent extraction and ...

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

    Directory of Open Access Journals (Sweden)

    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.

  19. Rapid Identification of Flavonoid Constituents Directly from PTP1B Inhibitive Extract of Raspberry (Rubus idaeus L.) Leaves by HPLC-ESI-QTOF-MS-MS.

    Science.gov (United States)

    Li, Zhuan-Hong; Guo, Han; Xu, Wen-Bin; Ge, Juan; Li, Xin; Alimu, Mireguli; He, Da-Jun

    2016-01-01

    Many potential health benefits of raspberry (Rubus idaeus L.) leaves were attributed to polyphenolic compounds, especially flavonoids. In this study, the methanol extract of R. idaeus leaves showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity with IC50 value of 3.41 ± 0.01 µg mL(-1) Meanwhile, a rapid and reliable method, employed high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry, was established for structure identification of flavonoids from PTP1B inhibitive extract of R. idaeus leaves using accurate mass measurement and characteristic fragmentation patterns. A total of 16 flavonoids, including 4 quercetin derivatives, 2 luteolin derivatives, 8 kaempferol derivatives and 2 isorhamnetin derivatives, were identified. Compounds 3: and 4: , Compounds 6: and 7: and Compounds 15: and 16: were isomers with different aglycones and different saccharides. Compounds 8: , 9: and 10: were isomers with the same aglycone and the same saccharide but different substituent positions. Compounds 11: and 12: were isomers with the same aglycone but different saccharides. Compounds 2: , 8: , 9: and 10: possessed the same substituent saccharide of glycuronic acid. Most of them were reported inR. idaeus for the first time. © The Author 2016. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

  20. Rapid Identification of Flavonoid Constituents Directly from PTP1B Inhibitive Extract of Raspberry (Rubus idaeus L.) Leaves by HPLC–ESI–QTOF–MS-MS

    Science.gov (United States)

    Li, Zhuan-Hong; Guo, Han; Xu, Wen-Bin; Ge, Juan; Li, Xin; Alimu, Mireguli; He, Da-Jun

    2016-01-01

    Many potential health benefits of raspberry (Rubus idaeus L.) leaves were attributed to polyphenolic compounds, especially flavonoids. In this study, the methanol extract of R. idaeus leaves showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity with IC50 value of 3.41 ± 0.01 µg mL−1. Meanwhile, a rapid and reliable method, employed high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry, was established for structure identification of flavonoids from PTP1B inhibitive extract of R. idaeus leaves using accurate mass measurement and characteristic fragmentation patterns. A total of 16 flavonoids, including 4 quercetin derivatives, 2 luteolin derivatives, 8 kaempferol derivatives and 2 isorhamnetin derivatives, were identified. Compounds 3 and 4, Compounds 6 and 7 and Compounds 15 and 16 were isomers with different aglycones and different saccharides. Compounds 8, 9 and 10 were isomers with the same aglycone and the same saccharide but different substituent positions. Compounds 11 and 12 were isomers with the same aglycone but different saccharides. Compounds 2, 8, 9 and 10 possessed the same substituent saccharide of glycuronic acid. Most of them were reported in R. idaeus for the first time. PMID:26896347

  1. Neuroprotection by flavonoids

    Directory of Open Access Journals (Sweden)

    Dajas F.

    2003-01-01

    Full Text Available The high morbidity, high socioeconomic costs and lack of specific treatments are key factors that define the relevance of brain pathology for human health and the importance of research on neuronal protective agents. Epidemiological studies have shown beneficial effects of flavonoids on arteriosclerosis-related pathology in general and neurodegeneration in particular. Flavonoids can protect the brain by their ability to modulate intracellular signals promoting cellular survival. Quercetin and structurally related flavonoids (myricetin, fisetin, luteolin showed a marked cytoprotective capacity in in vitro experimental conditions in models of predominantly apoptotic death such as that induced by medium concentrations (200 µM of H2O2 added to PC12 cells in culture. Nevertheless, quercetin did not protect substantia nigra neurons in vivo from an oxidative insult (6-hydroxydopamine, probably due to difficulties in crossing the blood-brain barrier. On the other hand, treatment of permanent focal ischemia with a lecithin/quercetin preparation decreased lesion volume, showing that preparations that help to cross the blood-brain barrier may be critical for the expression of the effects of flavonoids on the brain. The hypothesis is advanced that a group of quercetin-related flavonoids could become lead molecules for the development of neuroprotective compounds with multitarget anti-ischemic effects.

  2. Retention Study of Flavonoids Under Different Chromatographic Modes.

    Science.gov (United States)

    Sentkowska, Aleksandra; Biesaga, Magdalena; Pyrzynska, Krystyna

    2016-04-01

    The goal of this study was to investigate the chromatographic behavior of selected flavonoids from their different subgroups (flavonols, flavanones, flavones and isoflavones) in hydrophilic interaction liquid chromatography (HILIC). Chromatographic measurements were made on two different HILIC columns: cross-linked DIOL (Luna HILIC) and zwitterionic sulfoalkylbetaine (SeQuant ZIC-HILIC). Separation parameters such as the content of acetonitrile and pH of an eluent were studied. On the ZIC column, the retention factors of flavonoids increased with decreasing water content in the mobile phase. The increase in pH of the aqueous component mainly affects the polarity of the analytes. DIOL stationary phase shows more or less apparent dual retention mechanism, HILIC at the acetonitrile (ACN) content ≥75% and reversed phase (RP) with lower content of organic modifier. In the presence of ammonium acetate in the mobile phase, the retention of flavonoids onto the DIOL column increases without change in the selectivity of the separations. The similar effect, but considerably smaller was observed for aglycones on the ZIC column. The retention of studied glycosides (hesperidin, rutin) decreases in the presence of salt in the mobile phase. The significantly higher mass spectrometry sensitivity was observed under HILIC conditions in comparison with the most often used RP LC due to much higher content of ACN in the mobile phase. Finally, under optimal chromatographic conditions, the method was validated and applied for the determination of flavonoids in chamomile (Matricaria chamomilla L.) infusion. © The Author 2015. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

  3. Detection and Quantification of Glycosylated Flavonoid Malonates in Celery, Chinese Celery, and Celery Seed by LC-DAD-ESI/MS

    Science.gov (United States)

    Lin, Long-Ze; Lu, Shengmin; Harnly, James M.

    2013-01-01

    A screening method using LC-DAD-ESI/MS was applied to the analysis of flavonoids in celery, Chinese celery, and celery seeds (Apium graveolens L. and varieties). Fifteen flavonoid glycosides were detected in the three celery materials. They were identified as luteolin 7-O-apiosylglucoside, luteolin 7-O-glucoside, apigenin 7-O-apiosylglucoside, chrysoeriol 7-O-apiosylglucoside, chrysoeriol 7-O-glucoside, and more than 10 malonyl derivatives of these glycosides. The identification of the malonyl derivatives was confirmed by their conversion into glycosides upon heating and by comparison of some of the malonates with malonates that had previously been identified in red bell pepper and parsley. The concentrations of the glycosides and the malonyl glycosides in the three materials were estimated by comparison to aglycone standards. This is the first report of the presence of these glycosylated flavonoid malonates in celery. PMID:17253711

  4. Flavonoids and Asthma

    Science.gov (United States)

    Tanaka, Toshio; Takahashi, Ryo

    2013-01-01

    Asthma is a chronic disease, characterized by airway inflammation, airflow limitation, hyper-reactivity and airway remodeling. It is believed that asthma is caused by the interaction between genetic and environmental factors. The prevalence of allergic diseases, including asthma, has increased worldwide during the past two decades. Although the precise reasons that have caused this increase remain unknown, dietary change is thought to be one of the environmental factors. Flavonoids, which are polyphenolic plant secondary metabolites ubiquitously present in vegetables, fruits and beverages, possess antioxidant and anti-allergic traits, as well as immune-modulating activities. Flavonoids are powerful antioxidants and anti-allergic nutrients that inhibit the release of chemical mediators, synthesis of Th2 type cytokines, such as interleukin (IL)-4 and IL-13, and CD40 ligand expression by high-affinity immunoglobulin E (IgE) receptor-expressing cells, such as mast cells and basophils. They also inhibit IL-4-induced signal transduction and affect the differentiation of naïve CD4+ T cells into effector T-cells through their inhibitory effect on the activation of the aryl hydrocarbon receptor. Various studies of flavonoids in asthmatic animal models have demonstrated their beneficial effects. The results of several epidemiological studies suggest that an increase in flavonoid intake is beneficial for asthma. Moreover, clinical trials of flavonoids have shown their ameliorative effects on symptoms related to asthma. However, these human studies are currently limited; further validation is required to clarify whether an appropriate intake of flavonoids may constitute dietary treatment and for part of a preventive strategy for asthma. PMID:23752494

  5. 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

    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...... with natural hesperidin ("low dose"), orange juice treated with hesperidinase enzyme to yield hesperetin-7-glucoside, and orange juice fortified to obtain 3 times more hesperidin than naturally present ("high dose"). The area under the curve (AUC) for total plasma hesperetin of subjects consuming hesperetin-7......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...

  6. Dietary flavonoids and iodine Metabolism

    NARCIS (Netherlands)

    Elst, van der J.P.; Smit, J.W.A.; Romijn, H.A.; Heide, van der D.

    2003-01-01

    Flavonoids have inhibiting effects on the proliferation of cancer cells, including thyroidal ones. In the treatment of thyroid cancer the uptake of iodide is essential. Flavonoids are known to interfere with iodide organification ill vitro, and to cause goiter. The influence of flavonoids on iodine

  7. Flavonoids Fight Diseases

    Indian Academy of Sciences (India)

    Home; Journals; Resonance – Journal of Science Education; Volume 9; Issue 2. Flavonoids Fight Diseases. G Nagendrappa. Article-in-a-Box Volume 9 Issue 2 February 2004 pp 5-5. Fulltext. Click here to view fulltext PDF. Permanent link: http://www.ias.ac.in/article/fulltext/reso/009/02/0005-0005. Author Affiliations.

  8. Flavonoids and thyroid disease

    NARCIS (Netherlands)

    Heide, van der D.; Kastelijn, J.; Schroder-van der Elst, J.P.

    2003-01-01

    The most potent natural plant-derived compounds that can affect thyroid function, thyroid hormone secretion and availability to tissues is the group of flavonoids, i.e. plant pigments. They are present in our daily food, such as vegetables, fruits, grains, nuts, wine, and tea. Epidemiological

  9. Flavonoids Fight Diseases

    Indian Academy of Sciences (India)

    Home; Journals; Resonance – Journal of Science Education; Volume 9; Issue 2. Flavonoids Fight Diseases. G Nagendrappa. Article-in-a-Box Volume 9 Issue 2 February 2004 pp 5-5. Fulltext. Click here to view fulltext PDF. Permanent link: https://www.ias.ac.in/article/fulltext/reso/009/02/0005-0005. Author Affiliations.

  10. Factors modulating bioavailability of quercetin-related flavonoids and the consequences of their vascular function.

    Science.gov (United States)

    Terao, Junji

    2017-09-01

    Nowadays dietary flavonoids attract much attention in the prevention of chronic diseases. Epidemiological and intervention studies strongly suggest that flavonoid intake has beneficial effects on vascular health. It is unlikely that flavonoids act as direct antioxidants, although oxidative stress profoundly contributes to vascular impairment leading to cardiovascular diseases. Instead, flavonoids may exert their function by tuning the cellular redox state to an adaptive response or tolerable stress. However, the optimum intake of flavonoids from supplements or diet has not been clarified yet, because a number of exogenous and endogenous factors modulating their bioavailability affect their vascular function. This review will focus on the current knowledge of the bioavailability and vascular function of quercetin as a representative of antioxidative flavonoids. Current intervention studies imply that intake of quercetin-rich onion improves vascular health. Onion may be superior to quercetin supplement from the viewpoint of quercetin bioavailability, probably because the food matrix enhances the intestinal absorption of quercetin. α-Glucosylation increases its bioavailability by elevating the accessibility to the absorptive cells. Prenylation may enhance bioaccumulation at the target site by increasing the cellular uptake. However, these chemical modifications do not guarantee health benefits to the vascular system. Dietary quercetin is exclusively present as their conjugated form in the blood stream. Quercetin may exert its vascular function as an aglycone within macrophage cells after inflammation-induced deconjugation and as conjugated metabolites by targeting endothelial cells. The relationship between the bioavailability and bio-efficacy should be clarified, to evaluate the vascular function of a wide variety of dietary flavonoids. Copyright © 2017 Elsevier Inc. All rights reserved.

  11. Flavonoids from Mirabilis himalaica.

    Science.gov (United States)

    Li, Xue; Yin, Mingxia; Yang, Xuedong; Yang, Guang; Gao, Xian

    2018-02-05

    Six previously undescribed flavonoids, 2S-5-methoxy-6-methyl-7,2'-dihydroxyflavanone, 5,7,2'-trihydroxy-6-methylflavone, 5,7,6'-trihydroxy-6-methylcoumaronochromone, 2,4',6'-trihydroxy-2'-methoxy-3'-methylchalcone, 6R,11-dimethoxy-9-hydroxyrotenoid, and 6R,11-dimethoxy-9-hydroxy-10-methylrotenoid, along with eight known flavonoids, including 2S-5-methoxy-6-methyl-7,4'-dihydroxyflavanone, not previously reported as a natural product, and seven rotenoids, boeravinone A, B, D, P, F, coccineone B, and mirabijalone E, were isolated from the ethyl acetate soluble fraction of Mirabilis himalaica roots. Their structures were established by the extensive spectroscopic analysis, including HRESIMS, UV, NMR and ECD. All compounds were evaluated for their cytotoxic activities against three human cancer cell lines: A375 (melanoma), A549 (lung), and PLC (hepatoma). Copyright © 2018. Published by Elsevier B.V.

  12. Quercetin: a versatile flavonoid

    Directory of Open Access Journals (Sweden)

    Dr. Deepak Kumar Rai

    2007-07-01

    Full Text Available Associative evidence from observational and intervention studies in human subjects shows that a diet including plant foods (particularly fruit and vegetables rich in antioxidants conveys health benefits. There is no evidence that any particular nutrient or class of bioactive substances makes a special contribution to these benefits. Flavonoids occur naturally in fruits, vegetables and beverages such as tea and wine. Quercetin is the major flavonoid which belongs to the class called flavonols. Quercetin is found in many common foods including apples, tea, onions, nuts, berries, cauliflower, cabbage and many other foods. Quercetin provides many health promoting benefits, including improvement of cardiovascular health, eye diseases, allergic disorders, arthritis, reducing risk for cancers and many more. The main aim of this review is to obtain a further understanding of the reported beneficial health effects of Quercetin, its pharmacological effects, clinical application and also to evaluate its safety.

  13. Fingerprint profiles of flavonoid compounds from different Psidium guajava leaves and their antioxidant activities.

    Science.gov (United States)

    Wang, Lu; Wu, Yanan; Bei, Qi; Shi, Kan; Wu, Zhenqiang

    2017-10-01

    Flavonoids are the main active components in Psidium guajava leaves and have many multi-physiological functions. In this study, the flavonoid compositions were identified in the Psidium guajava leaves samples using a high-performance liquid chromatography with time-of-flight electrospray ionization mass spectrometry method. A high-performance liquid chromatography fingerprint method, combined with chemometrics, was used to perform a quality assessment of the Psidium guajava leaves samples. The eight identified flavonoid compounds including rutin, isoquercitrin, quercetin-3-O-β-d-xylopyranoside, quercetin-3-O-α-l-arabinopyranoside, avicularin, quercitrin, quercetin, and kaempferol were used as the chemical markers. The antioxidant activity of 15 batches of samples was examined using three different methods, and the results revealed the Psidium guajava leaves samples that had higher contents of the flavonoid compounds, glycoside and aglycone, possessed the highest antioxidant capacities. Consequently, a combination of chromatographic fingerprints and chemometric analyses was used for a quality assessment of Psidium guajava leaf tea and its derived products, which can lay the foundation for the development of plant tea resources or other herbs. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  14. Aglycone specificity of Escherichia coli alpha-xylosidase investigated by transxylosylation.

    Science.gov (United States)

    Kang, Min-Sun; Okuyama, Masayuki; Yaoi, Katsuro; Mitsuishi, Yasushi; Kim, Young-Min; Mori, Haruhide; Kim, Doman; Kimura, Atsuo

    2007-12-01

    The specificity of the aglycone-binding site of Escherichia coli alpha-xylosidase (YicI), which belongs to glycoside hydrolase family 31, was characterized by examining the enzyme's transxylosylation-catalyzing property. Acceptor specificity and regioselectivity were investigated using various sugars as acceptor substrates and alpha-xylosyl fluoride as the donor substrate. Comparison of the rate of formation of the glycosyl-enzyme intermediate and the transfer product yield using various acceptor substrates showed that glucose is the best complementary acceptor at the aglycone-binding site. YicI preferred aldopyranosyl sugars with an equatorial 4-OH as the acceptor substrate, such as glucose, mannose, and allose, resulting in transfer products. This observation suggests that 4-OH in the acceptor sugar ring made an essential contribution to transxylosylation catalysis. Fructose was also acceptable in the aglycone-binding site, producing two regioisomer transfer products. The percentage yields of transxylosylation products from glucose, mannose, fructose, and allose were 57, 44, 27, and 21%, respectively. The disaccharide transfer products formed by YicI, alpha-D-Xylp-(1-->6)-D-Manp, alpha-D-Xylp-(1-->6)-D-Fruf, and alpha-d-Xylp-(1-->3)-D-Frup, are novel oligosaccharides that have not been reported previously. In the transxylosylation to cello-oligosaccharides, YicI transferred a xylosyl moiety exclusively to a nonreducing terminal glucose residue by alpha-1,6-xylosidic linkages. Of the transxylosylation products, alpha-d-Xylp-(1-->6)-D-Manp and alpha-d-Xylp-(1-->6)-D-Fruf inhibited intestinal alpha-glucosidases.

  15. Sulfonation of glycopeptide antibiotics by sulfotransferase StaL depends on conformational flexibility of aglycone scaffold.

    Science.gov (United States)

    Shi, Rong; Munger, Christine; Kalan, Lindsay; Sulea, Traian; Wright, Gerard D; Cygler, Miroslaw

    2012-07-17

    Although glycopeptide antibiotics (GPAs), including vancomycin and teicoplanin, represent the most important class of anti-infective agents in the treatment of serious gram-positive bacterial infections, their usefulness is threatened by the emergence of resistant strains. GPAs are complex natural products consisting of a heptapeptide skeleton assembled via nonribosomal peptide synthesis and constrained through multiple crosslinks, with diversity resulting from enzymatic modifications by a variety of tailoring enzymes, which can be used to produce GPA analogues that could overcome antibiotic resistance. GPA-modifying sulfotransferases are promising tools for generating the unique derivatives. Despite significant sequence and structural similarities, these sulfotransferases modify distinct side chains on the GPA scaffold. To provide insight into the spatial diversity of modifications, we have determined the crystal structure of the ternary complex of bacterial sulfotransferase StaL with the cofactor product 3'-phosphoadenosine 5'-phosphate and desulfo-A47934 aglycone substrate. Desulfo-A47934 binds with the hydroxyl group on the 4-hydroxyphenylglycine in residue 1 directed toward the 3'-phosphoadenosine 5'-phosphate and hydrogen-bonded to the catalytic His67. Homodimeric StaL can accommodate GPA substrate in only one of the two active sites because of potential steric clashes. Importantly, the aglycone substrate demonstrates a flattened conformation, in contrast to the cup-shaped structures observed previously. Analysis of the conformations of this scaffold showed that despite the apparent rigidity due to crosslinking between the side chains, the aglycone scaffold displays substantial flexibility, important for enzymatic modifications by the GPA-tailoring enzymes. We also discuss the potential of using the current structural information in generating unique GPA derivatives.

  16. Triterpene galactosides of the pouoside class and corresponding aglycones from the sponge Lipastrotethya sp.

    Science.gov (United States)

    Lee, Jung-Ho; Jang, Kyoung Hwa; Lee, Yeon-Ju; Lee, Hyi-Seung; Sim, Chung J; Oh, Ki-Bong; Shin, Jongheon

    2011-12-27

    Nine new triterpene galactosides and aglycones, along with three known compounds from the rare pouoside class, were isolated from the tropical sponge Lipastrotethya sp. collected from Micronesia. The structures of these new compounds were determined by combined spectroscopic methods and designated as pouosides F-I (4, 8, 10, and 12) and pouogenins A-E (5-7, 9, and 11). The absolute configurations of the asymmetric centers and the cyclohexenone moiety, which had been previously undetermined, were assigned by NOESY analyses and Mosher's methods. Several of these compounds exhibited weak cytotoxicity against the K562 cell line.

  17. Identification and quantification of flavonoids in human urine samples by column switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry

    DEFF Research Database (Denmark)

    Nielsen, Salka E.; Freese, R.; Cornett, C.

    2000-01-01

    A rapid and sensitive high-performance liquid chromatographic mass spectrometric (HPLC-MS) method is described for the determination and quantification of 12 dietary flavonoid glycosides and aglycons in human urine samples. Chromatographic separation of the analytes of interest was achieved...... by column-switching, using the first column (a Zorbax 300SB C-3 column) for sample cleanup and eluting the heart-cut flavonoid fraction onto the second column (a Zorbax SE C-18 column) for separation and detection by ultraviolet and atmospheric pressure chemical ionization MS using single ion monitoring...... of variation for the analysis of the 12 different flavonoids in quality control urine samples were 12.3% on average (range 11.0-13.7%, n = 24, reproducibility) and the repeatability of the assay were 5.0% (mean, range 0.1-14.8%, it = 12). A subset of 10 urine samples from a human dietary intervention study...

  18. Study of Structure and Permeability Relationship of Flavonoids in Caco-2 Cells.

    Science.gov (United States)

    Fang, Yajing; Cao, Weiwei; Xia, Mengmeng; Pan, Siyi; Xu, Xiaoyun

    2017-11-29

    Flavonoids exhibit a broad range of biological activities. However, poor absorption of some flavonoids is a major limitation for use of flavonoids as nutraceuticals. To investigate the structure requirements for flavonoids intestinal absorption, transepithelial transport and cellular accumulation (CA) of 30 flavonoids were determined using the Caco-2 cell monolayer. The bilateral permeation of five types of flavonoids followed the order: flavanones ≥ isoflavones > flavones ≥ chalcones > flavonols. The concentration of flavonoids accumulated in cells did not correlate with cell penetration since the correlation coefficient between the apparent permeability coefficient ( P app ) and their corresponding CA was poor ( R ² < 0.3). Most flavonoids exhibited a ratio of 0.8-1.5 for P app A to B / P app B to A , suggesting passive diffusion pathways. However, luteolin, morin and taxifolin may involve the efflux mechanisms. The quantitative structure-permeability relationship (QSPR) study demonstrated that the intestinal absorption of flavonoids can be related to atomic charges on carbon 3' ( Q C3' ), molecule surface area ( S log P_V 3), balance between the center of mass and position of hydrophobic region ( vsurf_ID 1) and solvation energy of flavonoids ( E_sol ). These results provide useful information for initially screening of flavonoids with high intestinal absorption.

  19. Effect of variety, processing, and storage on the flavonoid glycoside content and composition of lettuce and endive.

    Science.gov (United States)

    DuPont, M S; Mondin, Z; Williamson, G; Price, K R

    2000-09-01

    Eight varieties of lettuce (Lactuca sativum) and three varieties of endive (Cichorium endivia) were analyzed for flavonoid composition and content. Total flavonoid contents, expressed as units of aglycon for fresh material, were in the ranges of 0.3-229 microg/g for lettuce and 44-248 microg/g for endive. Five quercetin conjugates [quercetin 3-O-galactoside, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, quercetin 3-O-(6-O-malonyl)glucoside, and quercetin 3-O-rhamnoside] and luteolin 7-O-glucuronide were measured in the green-leafed lettuce and an additional two cyanidin conjugates [cyanidin 3-O-glucoside and cyanidin 3-O-[(6-O-malonyl)glucoside

  20. Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans: A randomized, double-blind, crossover trial

    DEFF Research Database (Denmark)

    Nielsen, I.L.F.; Chee, W.S.S.; Bredsdorff, Lea

    2006-01-01

    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...... with natural hesperidin ("low dose"), orange juice treated with hesperidinase enzyme to yield hesperetin-7-glucoside, and orange juice fortified to obtain 3 times more hesperidin than naturally present ("high dose"). The area under the curve (AUC) for total plasma hesperetin of subjects consuming hesperetin-7......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...

  1. Flavonoids from Lonchocarpus muehlbergianus

    Directory of Open Access Journals (Sweden)

    Magalhães Aderbal F.

    2004-01-01

    Full Text Available The light petroleum extract from the roots of Lonchocarpus muehlbergianus Hassl contained nine flavonoids, including six new ones. These are 2,4-cis-2,4,5,8-tetramethoxy-(2,3:6,7-furanoflavan; 2,4-cis-4-hydroxy-2,5,8-trimethoxy-(2,3:6,7-furanoflavan; 2,4-cis-2-prenyloxy-4,5,8-trimethoxy-(2,3:6,7-fu-ranoflavan; 2,4-cis-2-prenyloxy-4-hydroxy-5,8-dimethoxy-(2,3:6,7-furanoflavan; 2',5',6'-trimethoxy-9-(1,1-dimethylallyoxy-[2,3:3,4]-furanochalcone; 5,6-dimethoxy-(2,3:7,8-furanoflavone, identi-fied by analysis of their spectral data (UV, IR, ¹H and 13C NMR, 2D-NMR, NOE and MS. The natural occurrence of 2,4-dioxygenated flavan derivatives is being reported for the first time. Quantitative analysis of the petrol extract, by using reversed-phase HPLC, showed that the most abundant flavonoid in the extract is 2,4-cis-2,4,5,8- tetramethoxy-(2,3:6,7-furanoflavan.

  2. Flavonoids from Agrimonia pilosa Ledeb: Free Radical Scavenging and DNA Oxidative Damage Protection Activities and Analysis of Bioactivity-Structure Relationship Based on Molecular and Electronic Structures.

    Science.gov (United States)

    Zhu, Liancai; Chen, Jinqiu; Tan, Jun; Liu, Xi; Wang, Bochu

    2017-02-26

    To clarify the substantial basis of the excellent antioxidant capacity of Agrimonia pilosa Ledeb. Fourteen flavonoids were isolated and identified from Agrimonia pilosa Ledeb, seven of which have notable DPPH radical scavenging activities, i.e., catechin, luteolin, quercetin, quercitrin, hyperoside, rutin, luteolin-7- O -β-glucoside with IC 50 values of 5.06, 7.29, 4.36, 7.12, 6.34, 6.36 and 8.12 µM, respectively. The DNA nicking assay showed that five flavonoids from Agrimonia pilosa Ledeb-taxifolin, catechin, hyperoside, quercitrin and rutin-have good protective activity against DNA oxidative damage. Further, we analyzed the bioactivity-structure relationship of these 14 flavonoids by applying quantum theory. According to their O-H bond dissociation enthalpy (BDE), C ring's spin density and stable molecular structure, the relationship between their structures and radical scavenging capacities was evaluated and clarified. We found that among flavonoid aglycones from Agrimonia pilosa Ledeb, the O-H BDE of quercetin is lowest with the values of 69.02 and the O-H BDE of apigenin is highest with the values of 79.77. It is interesting that the O-H BDE value of isovitexin (78.55) with glycoside at C-6 position is lower than that of its aglycone (79.77) and vitexin (99.20) with glycoside at C-8 position. Further analysis indicated that the glycosidation of flavonoids at C-6 in the A-ring makes a more uniform distribution of spin density and improves the stability of free radicals leading to the increase in antioxidant capacity. Flavonoids with good antioxidant capacity might contribute to the pharmacological effects of Agrimonia pilosa Ledeb.

  3. [Colorectal cancer prevention by flavonoids].

    Science.gov (United States)

    Hoensch, Harald; Richling, Elke; Kruis, Wolfgang; Kirch, Wilhelm

    2010-08-01

    Valid, sustained and safe clinical means of colorectal cancer prevention are still lacking, but they are urgently needed to lower the incidence of colorectal cancer. Dietary factors and phytochemicals such as flavonoids play an important role for prevention. A selective search of the literature using PubMed was performed with the following key words: flavonoids, cancer, therapy, colorectal cancer focused on clinical queries. Results of clinical studies including the authors' own were compared. In vivo and in vitro studies with animals, cell cultures and subcellular components provide ample evidence for antimutagenic and anticarcinogenic effects of flavonoids as shown for multiple biological and molecular endpoints. Isoflavonoids in vitro have been shown to induce proliferation of breast cancer cells. Epidemiologic trials (cohort, case-control and cross-sectional studies) yielded inconsistent results for flavonoid protection. Systematic reviews and meta-analyses support the protective role of tea flavonoids on adenoma incidence. An interventional pilot study with sustained flavonoid supplementation was shown to reduce the rate of neoplasia in patients with resected colorectal cancer. Selected flavonoids possess antimutagenic and anticarcinogenic properties and could reduce the incidence of colorectal neoplasias as shown in epidemiologic trials. Randomized controlled clinical studies with flavonoid intervention are necessary to provide evidence for their role in colorectal cancer prevention.

  4. Recent discoveries of anticancer flavonoids.

    Science.gov (United States)

    Raffa, Demetrio; Maggio, Benedetta; Raimondi, Maria Valeria; Plescia, Fabiana; Daidone, Giuseppe

    2017-12-15

    In this review we report the recent advances in anticancer activity of the family of natural occurring flavonoids, covering the time span of the last five years. The bibliographic data will be grouped, on the basis of biological information, in two great categories: reports in which the extract plants bioactivity is reported and the identification of each flavonoid is present or not, and reports in which the anticancer activity is attributable to purified and identified flavonoids from plants. Wherever possible, the targets and mechanisms of action as well as the structure-activity relationships of the molecules will be reported. Also, in the review it was thoroughly investigated the recent discovery on flavonoids containing the 2-phenyl-4H-chromen-4-one system even if some examples of unusual flavonoids, bearing a non-aromatic B-ring or other ring condensed to the base structure are reported. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  5. Effects of UV light and chromium ions on wood flavonoids

    International Nuclear Information System (INIS)

    Molnárné Hamvas, L.; Németh, K.; Stipta, J.

    2003-01-01

    The individual and simultaneous effect of UV light and chromium ions was investigated by spectrophotometric methods on inert surfaces impregnated with quercetin or robinetin. The UV-VIS spectra of the silica gel plates impregnated with these flavonoids were modified characteristically after irradiating ultraviolet light. Even a half an hour of irradiation has caused irreversible changes in the molecule structure. A certain chemical - presumably complexation - was concluded from the change of spectral bands assigned to flavonoids when impregnated with chromic ions. Hexavalent chromium caused more complex changes in the absorption spectra. The differences in the spectra could indicate either the oxidation and decomposition of flavonoids, or some kind of coordination process and the reduction of hexavalent chromium. The simultaneous application of UV light and chromium ions caused more pronounced effects. The complexation process between chromium(III) and flavonoid was completed

  6. Flavonoids from Pseudotsuga menziesii.

    Science.gov (United States)

    Krauze-Baranowska, Mirosława; Sowiński, Paweł; Kawiak, Anna; Sparzak, Barbara

    2013-01-01

    Four O-acylated flavonol glycosides, new in the plant kingdom, were isolated from the needles of Pseudotsuga menziesii. Their structures were established by 1D and 2D NMR and MS data as: daglesioside I [kaempferol 3-O-[2",5"-O-(4''',4(IV)-dihydroxy)-beta-truxinoyl]-alpha-L-arabinofuranoside] (1), daglesioside II [kaempferol 3-O-[2",5"-O-(4"'-hydroxy)-beta-truxinoyl]-alpha-L-arabinofuranoside] (2), daglesioside III [kaempferol 3-O-[2",5"-di-O-(E)-p-coumaroyl]-alpha-L-arabinofuranoside] (3), and daglesioside IV [kaempferol 3-O-[3",6"-di-O-(E)-cinnamoyl]-beta-D-glucopyranoside] (4). In addition, the known flavonoids (E)-tiliroside, (E)-ditiliroside, astragalin (kaempferol 3-O-beta-D-glucopyranoside), isorhamnetin, kaempferol, and quercetin were identified. The cytotoxic activity of compounds 1 and 3 was evaluated towards the HL-60, HeLa, and MDA-MB468 cell lines.

  7. Non-targeted chromatographic analyses of cuticular wax flavonoids from Physalis alkekengi L.

    Science.gov (United States)

    Kranjc, Eva; Albreht, Alen; Vovk, Irena; Makuc, Damjan; Plavec, Janez

    2016-03-11

    Since Chinese lantern (Physalis alkekengi L.) represents a rich source of various bioactive secondary metabolites, there is an urge for its detailed characterization. Non-polar flavonoid aglycones represent one of the few bioactive species found in plant's cuticular waxes. The separation of flavonoids is already extensively covered in the literature, but methods dedicated to separation and identification of methylated flavonoids are rather scarce. In the present study a non-targeted approach for the separation, isolation and identification of methylated flavonoids present in P. alkekengi L. var. franchetii cuticular waxes was established. A rapid and simple separation on HPTLC silica gel was developed for preliminary screening of flavonoids. Fast HPLC-UV-MS(n) and HPLC-UV methods using a C6-Phenyl and a C18 stationary phase were also developed, respectively. In both cases, the right combination of temperature and tetrahydrofuran, as a mobile phase modifier, were shown to be crucial for a baseline separation of all studied compounds. By employing a semi-preparative analog of the C18 column, a simultaneous isolation of pure unknown analytes was achieved. Using these developed methods in combination with NMR, four 3-O-methylated flavonols were detected and identified in P. alkekengi L. var. franchetii cuticular waxes: myricetin 3,7,3'-trimethyl ether, quercetin 3,7-dimethyl ether, myricetin 3,7,3',5'-tetramethyl ether and quercetin 3,7,3'-trimethyl ether. Moreover, the simple and fast isocratic HPLC-UV-MS(n) method (under 8min) should prove useful in quality control of P. alkekengi L. var. franchetii by enabling chromatographic fingerprinting of external methylated flavonols. Finally, a rationale for the mechanism of separation of these metabolites by HPLC is also given, which establishes a foundation for future development of chromatographic methods for methylated flavonols and related compounds. Copyright © 2016 Elsevier B.V. All rights reserved.

  8. A Comparative Analysis of the Photo-Protective Effects of Soy Isoflavones in Their Aglycone and Glucoside Forms

    Directory of Open Access Journals (Sweden)

    Barbara Iovine

    2012-12-01

    Full Text Available Isoflavones exist in nature predominantly as glucosides such as daidzin or genistin and are rarely found in their corresponding aglycone forms daidzein and genistein. The metabolism and absorption of isoflavones ingested with food is well documented, but little is known about their use as topical photo-protective agents. The aim of this study was to investigate in a comparative analysis the photo-protective effects of isoflavones in both their aglycone and glucoside forms. In human skin fibroblasts irradiated with 60 mJ/cm2 ultraviolet B (UVB, we measured the expression levels of COX-2 and Gadd45, which are involved in inflammation and DNA repair, respectively. We also determined the cellular response to UVB-induced DNA damage using the comet assay. Our findings suggest that both the isoflavone glucosides at a specific concentration and combination with an aglycone mixture exerted an anti-inflammatory and photo-protective effect that prevented 41% and 71% of UVB-induced DNA damage, respectively. The advantages of using either isoflavone glucosides or an aglycone mixture in applications in the field of dermatology will depend on their properties and their different potential uses.

  9. Exploiting the aglycon promiscuity of glycosyltransferase Bs-YjiC from Bacillus subtilis and its application in synthesis of glycosides.

    Science.gov (United States)

    Dai, Longhai; Li, Jiao; Yao, Peiyuan; Zhu, Yueming; Men, Yan; Zeng, Yan; Yang, Jiangang; Sun, Yuanxia

    2017-04-20

    Glycosylation is a prominent biological mechanism for structural and functional diversity of natural products. Uridine diphosphate-dependent glycosyltransferases with aglycon promiscuity are generally recognised as effective biocatalysts for glycodiversification of natural products for practical applications. In this study, the aglycon promiscuity of glycosyltransferase Bs-YjiC from Bacillus subtilis 168 was explored. Bs-YjiC, with uridine diphosphate glucose (UDPG) as sugar donor, exhibited robust capabilities to glycosylate 19 structurally diverse types of drug-like scaffolds with regio- and stereospecificities and form O-, N- and S-linkage glycosides. Twenty-four glycosides of 17 aglycons were purified from scale-up reactions using Bs-YjiC as a biocatalyst, and their structures were confirmed by nuclear magnetic resonance spectra. Furthermore, a one-pot reaction by coupling Bs-YjiC to sucrose synthase from Arabidopsis thaliana was applied to glycosylate pterostilbene. Without adding the costly UDPG as sugar donor, 9mM (3.8g/L) pterostilbene 4'-O-β-glucoside was obtained by periodic feeding of pterostilbene. These results suggest the aglycon promiscuity of Bs-YjiC and demonstrate its significant application prospect in biosynthesis of valuable natural products. Copyright © 2017 Elsevier B.V. All rights reserved.

  10. In-vitro effect of flavonoids from Solidago canadensis extract on glutathione S-transferase.

    Science.gov (United States)

    Apáti, Pál; Houghton, Peter J; Kite, Geoffrey; Steventon, Glyn B; Kéry, Agnes

    2006-02-01

    Solidago canadensis is typical of a flavonoid-rich herb and the effect of an aqueous ethanol extract on glutathione-S-transferase (GST) activity using HepG2 cells was compared with those of the flavonol quercetin and its glycosides quercitrin and rutin, found as major constituents. The composition of the extract was determined by HPLC and rutin was found to be the major flavonoidal component of the extract. Total GST activity was assessed using 1-chloro-2,4-dinitrobenzene as a substrate. The glycosides rutin and quercitrin gave dose-dependent increases in GST activity, with a 50% and 24.5% increase at 250 mM, respectively, while the aglycone quercetin inhibited the enzyme by 30% at 250 mM. The total extract of the herb gave an overall dose-dependent increase, the fractions corresponding to the flavonoids showed activating effects while those containing caffeic acid derivatives were inhibitory. The activity observed corresponds to that reported for similar compounds in-vivo using rats, thus the HepG2 cell line could serve as a more satisfactory method of assessing the effects of extracts and compounds on GST.

  11. 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)

  12. Comparative Analysis of Two Flavonol Synthases from Different-Colored Onions Provides Insight into Flavonoid Biosynthesis.

    Science.gov (United States)

    Park, Sangkyu; Kim, Da-Hye; Lee, Jong-Yeol; Ha, Sun-Hwa; Lim, Sun-Hyung

    2017-07-05

    We isolated cDNAs encoding flavonol synthase (FLS) from the red onion "H6" (AcFLS-H6) and the yellow onion "Hwangryongball" (AcFLS-HRB). We found three amino acid variations between the two sequences. Kinetic analysis with recombinant proteins revealed that AcFLS-HRB exhibited approximately 2-fold higher catalytic efficiencies than AcFLS-H6 for dihydroflavonol substrates and that both proteins preferred dihydroquercetin to dihydrokaempferol. The expression patterns of flavonoid biosynthesis genes corresponded to the accumulation patterns of flavonoid aglycones in both onions. Whereas the other flavonoid biosynthesis genes were weakly expressed in the HRB sheath compared to that of H6, the expression of FLS was similar in both onions. This relatively enhanced FLS expression, along with the higher activity of AcFLS-HRB, could increase the quercetin production in the HRB sheath. The quercetin content was approximately 12-fold higher than the cyanidin content in the H6 sheath, suggesting that FLS has priority in the competition between FLS and dihydroflavonol 4-reductase (DFR) for their substrate dihydroquercetin.

  13. Flavonoid Glycosides from Siparuna gigantotepala Leaves and Their Antioxidant Activity.

    Science.gov (United States)

    Torres Castañeda, Harlen Gerardo; Colmenares Dulcey, Ana Julia; Isaza Martínez, José Hipólito

    2016-01-01

    Two new flavonol glycosides were isolated from the leaves of Siparuna gigantotepala. Their structures were determined to be kaempferol 3-O-β-xylopyranosyl-(1→2)-α-arabinofuranoside (1) and kaempferol 3,7-di-O-methyl-4'-O-α-rhamnopyranosyl-(1→2)-β-glucopyranoside (2). In addition, three known flavonol glycosides, rutin (3), kaempferol 3-O-rutinoside (4), and kaempferol 3,7-di-O-methyl-4'-O-rutinoside (5), and three flavonol aglycones, quercetin (6), kaempferol 3,7-dimethyl ether (7), and kaempferol 3,7,4'-trimethyl ether (8), were also isolated and are reported here for the first time in this species. The structures of compounds 1 and 2 were established on the basis of their LC-MS and one- and two-dimensional (1D)- and (2D)-NMR spectroscopic analyses, combined with acid methanolysis and silylation of sugar moieties for GC-MS. Evaluation of the antioxidant activity, conducted in the 96-well plate format, showed that the flavonoids isolated possess strong 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity and moderate oxygen radical absorption capacity.

  14. Flavonoid-surfactant interactions: A detailed physicochemical study

    Science.gov (United States)

    Singh, Onkar; Kaur, Rajwinder; Mahajan, Rakesh Kumar

    2017-01-01

    The aim of this article is to study the interactions between flavonoids and surfactants with attention of finding the probable location of flavonoids in micellar media that can be used for controlling their antioxidant behavior. In present study, the micellar and interfacial behavior of twin tailed anionic surfactants viz. sodium bis(2-ethylhexyl)sulfosuccinate (AOT) and sodium bis(2-ethylhexyl)phosphate (NaDEHP) in the presence of two flavonoids, namely quercetin (QUE) and kaempferol (KFL) have been studied by surface tension measurements. UV-visible, fluorescence and differential pulse voltammetric (DPV) measurements have been employed to predict the probable location of flavonoids (QUE/KFL) within surfactant (AOT/NaDEHP) aggregates. Dynamic light scattering (DLS) measurements further confirmed the solubilization of QUE/KFL in AOT/NaDEHP aggregates deduced from increased hydrodynamic diameter (Dh) of aggregates in the presence of flavonoids. Both radical scavenging activity (RSA) and degradation rate constant (k) of flavonoids are found to be higher in NaDEHP micelles as compared to AOT micelles.

  15. Plant growth inhibiting flavonoids in exudate of Cistus ladanifer and in associated soils.

    Science.gov (United States)

    Chaves, N; Sosa, T; Escudero, J C

    2001-03-01

    Of the aglycone flavonoids identified in the exudate of cistus ladanifer, two, the flavone apigenin-4'-(O)-methyl and the flavonol kaempferol-3,7-di(O)-methyl inhibit development of the seedlings of Rumex crispus at 0.5 and 1 mM. Additive effects were observed between the major flavonols of the exudate kaempferol-3-(O)-methyl and kaempferol-3,7-di-(O)-methyl in inhibiting the size of the cotyledons and delaying the germination and cotyledon emergence. The presence of apigenin-4'-(O)-methyl, kaempferol-3,7-di-(O)-methyl, and kaempferol-3-(O)-methyl was detected in the soils associated with C. ladanifer during the summer and autumn months. That these compounds are present in the soil and are not restricted to the leaves provides support for the hypothesis that C. ladanifer has allelopathic potential.

  16. Flavonoid intake and bone health.

    Science.gov (United States)

    Weaver, Connie M; Alekel, D Lee; Ward, Wendy E; Ronis, Martin J

    2012-01-01

    Flavonoids, found in a wide diversity of plant foods from fruits and vegetables, herbs and spices, essential oils, and beverages, have the most potential of dietary components for promotion of bone health beyond calcium and vitamin D. Recent epidemiological studies show flavonoid consumption to have a stronger association with bone than general fruit and vegetable consumption. Bioactive flavonoids are being assessed for properties beyond their chemical antioxidant capacity, including anti-inflammatory actions. Some have been reported to enhance bone formation and to inhibit bone resorption through their action on cell signaling pathways that influence osteoblast and osteoclast differentiation. Future research is needed to determine which of the flavonoids and their metabolites are most effective and at what dose, as well as the mechanism of modulating cellular events, in order to set priorities for clinical trials.

  17. Microbial biotransformation of bioactive flavonoids.

    Science.gov (United States)

    Cao, Hui; Chen, Xiaoqing; Jassbi, Amir Reza; Xiao, Jianbo

    2015-01-01

    The bioactive flavonoids are considered as the most important phytochemicals in food, which exert a wide range of biological benefits for human being. Microbial biotransformation strategies for production of flavonoids have attracted considerable interest because they allow yielding novel flavonoids, which do not exist in nature. In this review, we summarize the existing knowledge on the production and biotransformation of flavonoids by various microbes. The main reactions during microbial biotransformation are hydroxylation, dehydroxylation, O-methylation, O-demethylation, glycosylation, deglycosylation, dehydrogenation, hydrogenation, C ring cleavage of the benzo-γ-pyrone system, cyclization, and carbonyl reduction. Cunninghamella, Penicillium, and Aspergillus strains are very popular to biotransform flavonoids and they can perform almost all the reactions with excellent yields. Aspergillus niger is one of the most applied microorganisms in the flavonoids' biotransformation; for example, A. niger can transfer flavanone to flavan-4-ol, 2'-hydroxydihydrochalcone, flavone, 3-hydroxyflavone, 6-hydroxyflavanone, and 4'-hydroxyflavanone. The hydroxylation of flavones by microbes usually happens on the ortho position of hydroxyl group on the A ring and C-4' position of the B ring and microbes commonly hydroxylate flavonols at the C-8 position. The microorganisms tend to hydroxylate flavanones at the C-5, 6, and 4' positions; however, for prenylated flavanones, dihydroxylation often takes place on the C4α=C5α double bond on the prenyl group (the side chain of A ring). Isoflavones are usually hydroxylated at the C-3' position of the B ring by microorganisms. The microbes convert flavonoids to their 7-O-glycosides and 3-O-glycosides (when flavonoids have a hydroxyl moiety at the C-3 position). The demethylation of multimethoxyl flavonoids by microbes tends to happen at the C-3' and C-4' positions of the B ring. Multimethoxyl flavanones and isoflavone are demethylated at

  18. Mixture-Amount Design and Response Surface Modeling to Assess the Effects of Flavonoids and Phenolic Acids on Developmental Performance of Anastrepha ludens

    OpenAIRE

    Pascacio-Villafán, Carlos; Lapointe, Stephen; Williams, Trevor; Sivinski, John; Niedz, Randall; Aluja, Martín

    2014-01-01

    Host plant resistance to insect attack and expansion of insect pests to novel hosts may to be modulated by phenolic compounds in host plants. Many studies have evaluated the role of phenolics in host plant resistance and the effect of phenolics on herbivore performance, but few studies have tested the joint effect of several compounds. Here, we used mixture-amount experimental design and response surface modeling to study the effects of a variety of phenolic compounds on the development and s...

  19. Comparative Study of the Effect of Sample Pretreatment and Extraction on the Determination of Flavonoids from Lemon (Citrus limon)

    Science.gov (United States)

    Ledesma-Escobar, Carlos A.; Priego-Capote, Feliciano; Luque de Castro, María D.

    2016-01-01

    Background Flavonoids have shown to exert multiple beneficial effects on human health, being also appreciated by both food and pharmaceutical industries. Citrus fruits are a key source of flavonoids, thus promoting studies to obtain them. Characteristics of these studies are the discrepancies among sample pretreatments and among extraction methods, and also the scant number of comparative studies developed so far. Objective Evaluate the effect of both the sample pretreatment and the extraction method on the profile of flavonoids isolated from lemon. Results Extracts from fresh, lyophilized and air-dried samples obtained by shaking extraction (SE), ultrasound-assisted extraction (USAE), microwave-assisted extraction (MAE) and superheated liquid extraction (SHLE) were analyzed by LC–QTOF MS/MS, and 32 flavonoids were tentatively identified using MS/MS information. ANOVA applied to the data from fresh and dehydrated samples and from extraction by the different methods revealed that 26 and 32 flavonoids, respectively, were significant (p≤0.01). The pairwise comparison (Tukey HSD; p≤0.01) showed that lyophilized samples are more different from fresh samples than from air-dried samples; also, principal component analysis (PCA) showed a clear discrimination among sample pretreatment strategies and suggested that such differences are mainly created by the abundance of major flavonoids. On the other hand, pairwise comparison of extraction methods revealed that USAE and MAE provided quite similar extracts, being SHLE extracts different from the other two. In this case, PCA showed a clear discrimination among extraction methods, and their position in the scores plot suggests a lower abundance of flavonoids in the extracts from SHLE. In the two PCA the loadings plots revealed a trend to forming groups according to flavonoid aglycones. Conclusions The present study shows clear discrimination caused by both sample pretreatments and extraction methods. Under the studied

  20. Comparative Study of the Effect of Sample Pretreatment and Extraction on the Determination of Flavonoids from Lemon (Citrus limon.

    Directory of Open Access Journals (Sweden)

    Carlos A Ledesma-Escobar

    Full Text Available Flavonoids have shown to exert multiple beneficial effects on human health, being also appreciated by both food and pharmaceutical industries. Citrus fruits are a key source of flavonoids, thus promoting studies to obtain them. Characteristics of these studies are the discrepancies among sample pretreatments and among extraction methods, and also the scant number of comparative studies developed so far.Evaluate the effect of both the sample pretreatment and the extraction method on the profile of flavonoids isolated from lemon.Extracts from fresh, lyophilized and air-dried samples obtained by shaking extraction (SE, ultrasound-assisted extraction (USAE, microwave-assisted extraction (MAE and superheated liquid extraction (SHLE were analyzed by LC-QTOF MS/MS, and 32 flavonoids were tentatively identified using MS/MS information. ANOVA applied to the data from fresh and dehydrated samples and from extraction by the different methods revealed that 26 and 32 flavonoids, respectively, were significant (p≤0.01. The pairwise comparison (Tukey HSD; p≤0.01 showed that lyophilized samples are more different from fresh samples than from air-dried samples; also, principal component analysis (PCA showed a clear discrimination among sample pretreatment strategies and suggested that such differences are mainly created by the abundance of major flavonoids. On the other hand, pairwise comparison of extraction methods revealed that USAE and MAE provided quite similar extracts, being SHLE extracts different from the other two. In this case, PCA showed a clear discrimination among extraction methods, and their position in the scores plot suggests a lower abundance of flavonoids in the extracts from SHLE. In the two PCA the loadings plots revealed a trend to forming groups according to flavonoid aglycones.The present study shows clear discrimination caused by both sample pretreatments and extraction methods. Under the studied conditions, liophilization provides

  1. Comparative Study of the Effect of Sample Pretreatment and Extraction on the Determination of Flavonoids from Lemon (Citrus limon).

    Science.gov (United States)

    Ledesma-Escobar, Carlos A; Priego-Capote, Feliciano; Luque de Castro, María D

    2016-01-01

    Flavonoids have shown to exert multiple beneficial effects on human health, being also appreciated by both food and pharmaceutical industries. Citrus fruits are a key source of flavonoids, thus promoting studies to obtain them. Characteristics of these studies are the discrepancies among sample pretreatments and among extraction methods, and also the scant number of comparative studies developed so far. Evaluate the effect of both the sample pretreatment and the extraction method on the profile of flavonoids isolated from lemon. Extracts from fresh, lyophilized and air-dried samples obtained by shaking extraction (SE), ultrasound-assisted extraction (USAE), microwave-assisted extraction (MAE) and superheated liquid extraction (SHLE) were analyzed by LC-QTOF MS/MS, and 32 flavonoids were tentatively identified using MS/MS information. ANOVA applied to the data from fresh and dehydrated samples and from extraction by the different methods revealed that 26 and 32 flavonoids, respectively, were significant (p≤0.01). The pairwise comparison (Tukey HSD; p≤0.01) showed that lyophilized samples are more different from fresh samples than from air-dried samples; also, principal component analysis (PCA) showed a clear discrimination among sample pretreatment strategies and suggested that such differences are mainly created by the abundance of major flavonoids. On the other hand, pairwise comparison of extraction methods revealed that USAE and MAE provided quite similar extracts, being SHLE extracts different from the other two. In this case, PCA showed a clear discrimination among extraction methods, and their position in the scores plot suggests a lower abundance of flavonoids in the extracts from SHLE. In the two PCA the loadings plots revealed a trend to forming groups according to flavonoid aglycones. The present study shows clear discrimination caused by both sample pretreatments and extraction methods. Under the studied conditions, liophilization provides extracts

  2. Mixture-amount design and response surface modeling to assess the effects of flavonoids and phenolic acids on developmental performance of Anastrepha ludens.

    Science.gov (United States)

    Pascacio-Villafán, Carlos; Lapointe, Stephen; Williams, Trevor; Sivinski, John; Niedz, Randall; Aluja, Martín

    2014-03-01

    Host plant resistance to insect attack and expansion of insect pests to novel hosts may to be modulated by phenolic compounds in host plants. Many studies have evaluated the role of phenolics in host plant resistance and the effect of phenolics on herbivore performance, but few studies have tested the joint effect of several compounds. Here, we used mixture-amount experimental design and response surface modeling to study the effects of a variety of phenolic compounds on the development and survival of Mexican fruit fly (Anastrepha ludens [Loew]), a notorious polyphagous pest of fruit crops that is likely to expand its distribution range under climate change scenarios. (+)- Catechin, phloridzin, rutin, chlorogenic acid, and p-coumaric acid were added individually or in mixtures at different concentrations to a laboratory diet used to rear individuals of A. ludens. No effect was observed with any mixture or concentration on percent pupation, pupal weight, adult emergence, or survival from neonate larvae to adults. Larval weight, larval and pupal developmental time, and the prevalence of adult deformities were affected by particular mixtures and concentrations of the compounds tested. We suggest that some combinations/concentrations of phenolic compounds could contribute to the management of A. ludens. We also highlight the importance of testing mixtures of plant secondary compounds when exploring their effects upon insect herbivore performance, and we show that mixture-amount design is a useful tool for this type of experiments.

  3. Structure, bioactivity, and synthesis of methylated flavonoids.

    Science.gov (United States)

    Wen, Lingrong; Jiang, Yueming; Yang, Jiali; Zhao, Yupeng; Tian, Miaomiao; Yang, Bao

    2017-06-01

    Methylated flavonoids are an important type of natural flavonoid derivative with potentially multiple health benefits; among other things, they have improved bioavailability compared with flavonoid precursors. Flavonoids have been documented to have broad bioactivities, such as anticancer, immunomodulation, and antioxidant activities, that can be elevated, to a certain extent, by methylation. Understanding the structure, bioactivity, and bioavailability of methylated flavonoids, therefore, is an interesting topic with broad potential applications. Though methylated flavonoids are widely present in plants, their levels are usually low. Because developing efficient techniques to produce these chemicals would likely be beneficial, we provide an overview of their chemical and biological synthesis. © 2017 New York Academy of Sciences.

  4. Flavonoids and phenolic acids of Nepeta cataria L. var. citriodora (Becker) Balb. (Lamiaceae).

    Science.gov (United States)

    Modnicki, Daniel; Tokar, Magdalena; Klimek, Barbara

    2007-01-01

    Luteolin 7-O-glucuronide, luteolin 7-O-glucurono-(1-->6)-glucoside, apigenin 7-O-glucuronide as well as free aglycones luteolin and apigenin have been isolated from lemon catnip herb (Nepeta cataria L. var citriodora). Luteolin 7-O-glucurono-(1-->6)-glucoside is probably a new compound, for the first time described. Two minor constituents of flavonoid fraction have been identified as apigenin 7-O-glucoside and luteolin 7-O-glucoside by means of HPLC method. The percentage of total flavonoids determined by use of spectrophotometric method was in the range from 0.30 to 0.46% of dry mass. In phenolic acid fraction, caffeic, rosmarinic and p-coumaric acids have been identified. Total amount of phenolic acids determined by spectrophotometric method was in the range of 0.75% to 1.4 % and the content of rosmarinic acid quantified by HPLC method fluctuated in the wide range from 0.06% to 0.15% depending on the sample. The results of the investigations showed that the composition of flavonoid compounds and phenolic acids in lemon catnip are similar to those in lemon balm (Melissa officinalis L.). The amount of flavonoids are similar in both plants, and the percentage of rosmarinic acid is about ten times lower in lemon catnip than in lemon balm. The presence of luteolin, apigenin and their glycosides, caffeic acid as well as the previously described terpenoids (ursolic acid, citral, nerol. geraniol) suggests the possibility of the use of lemon catnip herb as a constituent of phytopharmaceutical preparations with mild sedative, antispasmodic, antioxidative and antiinflammatory action.

  5. Flavonoids are systemically induced by UV-B in Zea mays

    International Nuclear Information System (INIS)

    Tossi, V.E.; Lamattina, L.; Cassia, R.

    2009-01-01

    Flavonoid concentration is increased by UV-B irradiation, but it is unknown if this is a local or systemic response. Nitric oxide (NO) is a diffusible molecule involved in the UV-B response. NO regulates the expression of chalcone synthase (CHS), a key enzyme in the synthesis of flavonoids. The aim of this work was to determine if maize flavonoids are local or systemically induced by UV-B, and what is the participation of NO in this response. We have used maize seedlings where the second leaf was sprayed with H 2 O or cPTIO (a NO scavenger), and then completely covered (C), partially covered (P) or uncovered (U) before to be UV-B irradiated. The results show a 60% increase in the NO concentration of U, 42% in P and 35% in C respectively. Flavonoid concentration increased 90% in C, 70% in P and 40% in U. Flavonoid concentration was reduced when leaves were pretreated with cPTIO before the UV-B irradiation. RT-PCR shows that CHS was up-regulated by UV-B in U, P and C, but downregulated with cPTIO. We have analyzed the subcellular localization of flavonoid and NO in UV-B irradiated plants. Flavonoid localization was coincident with the NO presence in the irradiated surface of the leaves and flavonoids were detected in vesicles. These results indicate that flavonoids are systemically induced by UV-B in a NO-related mechanism. (authors)

  6. Anti-Photoaging Effects of Soy Isoflavone Extract (Aglycone and Acetylglucoside Form from Soybean Cake

    Directory of Open Access Journals (Sweden)

    Chi-Feng Hung

    2010-11-01

    Full Text Available Soy isoflavones, found in soybean and soybean products, have been reported to possess many physiological activities such as antioxidant activity, inhibition of cancer cell proliferation, reduction of cardiovascular risk, prevention of osteoporosis and alleviation of postmenopausal syndrome. In our previous study, soy isoflavone extract ISO-1 (containing 12 soy isoflavones from soybean cake was demonstrated to prevent skin damage caused by UVB exposure. In this study, soy isoflavone extract from soybean cake was further purified and evaluated for the protective effects on UVB-induced damage. The results revealed that Fraction 3, which contains the aglycone group (daidzein, genistein and glycitein and acetylglucoside group (acetyldaidzin, acetylgenistin and acetylglycitin of soy isoflavones, could inhibit UVB-induced death of human keratinocytes and reduce the level of desquamation, transepidermal water loss (TEWL, erythema and epidermal thickness in mouse skin. Furthermore, topical application of Fraction 3 increased the activity of catalase and suppressed cyclooxygenase-2 (COX-2 and proliferating cell nuclear antigen (PCNA expression in mice exposed to UVB. In addition, in comparison with ISO-1 and genistein, the Fraction 3 possessed much greater protective effects on both UVB-induced oxidative stress and keratinocyte death than other fractions. Therefore, the soy isoflavone extract Fraction 3 from soybean cake is a desirable anti-photoaging agent for skin care.

  7. Simultaneous determination of phenylethanoid glycosides and aglycones by capillary zone electrophoresis with running buffer modifier.

    Science.gov (United States)

    Dong, Shuqing; Gao, Ruibin; Yang, Yan; Guo, Mei; Ni, Jingman; Zhao, Liang

    2014-03-15

    Although the separation efficiency of capillary electrophoresis (CE) is much higher than that of other chromatographic methods, it is sometimes difficult to adequately separate the complex ingredients in biological samples. This article describes how one effective and simple way to develop the separation efficiency in CE is to add some modifiers to the running buffer. The suitable running buffer modifier β-cyclodextrin (β-CD) was explored to fast and completely separate four phenylethanoid glycosides and aglycones (homovanillyl alcohol, hydroxytyrosol, 3,4-dimethoxycinnamic acid, and caffeic acid) in Lamiophlomis rotata (Lr) and Cistanche by capillary zone electrophoresis with ultraviolet (UV) detection. It was found that when β-CD was used as running buffer modifier, a baseline separation of the four analytes could be accomplished in less than 20 min and the detection limits were as low as 10(-3) mg L(-1). Other factors affecting the CE separation, such as working potential, pH value and ionic strength of running buffer, separation voltage, and sample injection time, were investigated extensively. Under the optimal conditions, a successful practical application on the determination of Lr and Cistanche samples confirmed the validity and practicability of this method. Copyright © 2014 Elsevier Inc. All rights reserved.

  8. Benefit of Oleuropein Aglycone for Alzheimer’s Disease by Promoting Autophagy

    Directory of Open Access Journals (Sweden)

    Joaquín G. Cordero

    2018-01-01

    Full Text Available Alzheimer’s disease is a proteinopathy characterized by accumulation of hyperphosphorylated Tau and β-amyloid. Autophagy is a physiological process by which aggregated proteins and damaged organelles are eliminated through lysosomal digestion. Autophagy deficiency has been demonstrated in Alzheimer’s patients impairing effective elimination of aggregates and damaged mitochondria, leading to their accumulation, increasing their toxicity and oxidative stress. In the present study, we demonstrated by microarray analysis the downregulation of fundamental autophagy and mitophagy pathways in Alzheimer’s patients. The benefits of the Mediterranean diet on Alzheimer’s disease and cognitive impairment are well known, attributing this effect to several polyphenols, such as oleuropein aglycone (OLE, present in extra virgin olive oil. OLE is able to induce autophagy, achieving a decrease of aggregated proteins and a reduction of cognitive impairment in vivo. This effect is caused by the modulation of several pathways including the AMPK/mTOR axis and the activation of autophagy gene expression mediated by sirtuins and histone acetylation or EB transcription factor. We propose that supplementation of diet with extra virgin olive oil might have potential benefits for Alzheimer’s patients by the induction of autophagy by OLE.

  9. Ultrasound-Assisted Extraction of Total Flavonoids from Corn Silk and Their Antioxidant Activity

    Directory of Open Access Journals (Sweden)

    Ling-Li Zheng

    2016-01-01

    Full Text Available Object. Ultrasound-assisted extraction of total flavonoids from corn silk and their antioxidant activities were studied. Methods. Response surface methodology was adopted to optimize the extraction conditions and antioxidant activities of the extracted total flavonoids were detected through ferric reducing antioxidant power (FRAP assay. Results. Through a three-level, three-variable Box-Behnken design of response surface methodology (RSM adopting yield as response, the optimal conditions were determined as follows: ultrasonic power 500 W, extraction time 20 min, material solvent ratio 1 : 20, and ethanol concentration 30%. Under the optimum conditions, the extraction yield of total flavonoids was 1.13%. FRAP value of total flavonoids extracted from corn silk was 467.59 μmol/L. Conclusion. The total flavonoids of corn silk could be developed as food natural antioxidant reagents.

  10. Extraction and Purification of Flavonoids from Radix Puerariae | Li ...

    African Journals Online (AJOL)

    Purpose: To develop an efficient method for the purification of flavonoids from Radix puerariae. Methods: Optimal extraction technology was obtained using orthogonal test. Through adsorption and desorption tests, 8 resins with different polarity, diameter, and surface area were studied. Finally, a novel macroporous resin, ...

  11. Bioconversion of isoflavone glycosides to aglycones, mineral bioavailability and vitamin B complex in fermented soymilk by probiotic bacteria and yeast.

    Science.gov (United States)

    Rekha, C R; Vijayalakshmi, G

    2010-10-01

    To study the role of β-glucosidase producing probiotic bacteria and yeast in the biotransformation of isoflavone glycosides to aglycones, mineral bioavailability and vitamin B complex in fermented soymilk. Five isolates of probiotic lactic acid bacteria (LAB), Lactobacillus acidophilus B4496, Lactobacillus bulgaricus CFR2028, Lactobacillus casei B1922, Lactobacillus plantarum B4495 and Lactobacillus fermentum B4655 with yeast Saccharomyces boulardii were used to ferment soymilk to obtain the bioactive isoflavones, genistein and daidzein. High-performance liquid chromatography was used to analyse the concentration of isoflavones. Bioactive aglycones genistein and daidzein after 24 and 48 h of fermentation ranged from 97.49 to 98.49% and 62.71 to 92.31% respectively with different combinations of LAB with yeast. Increase in bioavailability of minerals and vitamin B complex were also observed in fermented soymilk. LAB in combination with yeast S. boulardii has great potential for the enrichment of bioactive isoflavones, enhancing the viability of LAB strains, decreasing the antinutrient phytic acid and increasing the mineral bioavailability in soymilk fermentation. Fermentation of soymilk with probiotic organisms improves the bioavailability of isoflavones, assists in digestion of protein, provides more soluble calcium, enhances intestinal health and supports immune system. Increased isoflavone aglycone content in fermented soymilk improves the biological functionality of soymilk. © 2010 The Authors. Journal compilation © 2010 The Society for Applied Microbiology.

  12. Modification of flavonoid biosynthesis in crop plants

    NARCIS (Netherlands)

    Schijlen, E.G.W.M.; Vos, de C.H.; Tunen, van A.J.; Bovy, A.G.

    2004-01-01

    Flavonoids comprise the most common group of polyphenolic plant secondary metabolites. In plants, flavonoids play an important role in biological processes. Beside their function as pigments in flowers and fruits, to attract pollinators and seed dispersers, flavonoids are involved in UV-scavenging,

  13. Flavonoids and volatiles in Chrysanthemum morifolium Ramat ...

    African Journals Online (AJOL)

    Flavonoids and volatiles in a traditional herbal medicine Chrysanthemum morifolium Ramat flower were determined by HPLC and GC/MS, respectively. Eight flavonoids and fifty eight volatiles were identified. Luteolin-7-glucoside and quercitrin were the most abundant flavonoids and they amounted for 85.7% of the total ...

  14. Analysis and health effects of flavonoids.

    NARCIS (Netherlands)

    Hollman, P.C.H.; Hertog, M.G.L.; Katan, M.B.

    1996-01-01

    Flavonoids are polyphenolic compounds that occur ubiquitously in foods of plant origin. Over 4000 different flavonoids have been described. Flavonoids have a variety of biological effects in numerous mammalian cell systems, in vitro as well as in vivo. Recently much attention has been paid to their

  15. Antimicrobial action of purified raspberry flavonoid

    African Journals Online (AJOL)

    user

    2012-02-07

    Feb 7, 2012 ... In this paper, the bacteriostatic action of purified raspberry flavonoid was explored. A study was conducted on the effect of raspberry flavonoid on Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Saccharomyces cerevisiae, Rhizopus, Mucor and Penicillium. Raspberry flavonoid had the best.

  16. The effect of quercetin and kaempferol aglycones and glucuronides on peroxisome proliferator-activated receptor-gamma (PPAR-¿)

    NARCIS (Netherlands)

    Beekmann, K.; Rubió, L.; Haan, de L.H.J.; Actis Goretta, L.; Burg, van der B.; Bladeren, van P.J.; Rietjens, I.M.C.M.

    2015-01-01

    The consumption of dietary flavonoids has been associated with a variety of health benefits, including effects mediated by the activation of peroxisome proliferator-activated receptor-gamma (PPAR-¿). Flavonoids are extensively metabolized during and after uptake and there is little known on the

  17. Anthocyanin from strawberry (Fragaria ananassa) with the novel aglycone, 5-carboxypyranopelargonidin.

    Science.gov (United States)

    Andersen, Øyvind M; Fossen, Torgils; Torskangerpoll, Kjell; Fossen, Arve; Hauge, Unni

    2004-02-01

    An anthocyanin, 1, with the novel 4-substituted aglycone, 5-carboxypyranopelargonidin, was isolated in small amounts from the acidified, methanolic extract of strawberries, Fragaria ananassa Duch., by preparative HPLC after purification by partition against ethyl acetate, Amberlite XAD-7 and Sephadex LH-20 column chromatography. It was identified mainly by 2D NMR spectroscopy and electrospray LC-MS as the 3-O-beta-glucopyranoside of 5-carboxy-2-(4-hydroxyphenyl)-3,8-dihydroxy-pyrano[4,3,2-de]-1-benzopyrylium, an anthocyanidin which is homologous to 5-carboxypyranomalvidin (vitisidin A) reported in red wines and 5-carboxypyranocyanidin recently isolated from red onions. By comparison of UV-Vis absorption spectra, 1 showed in contrast to 2, pelargonidin 3-O-beta-glucopyranoside, a local absorption peak around 360 nm, a hypsochromic shift (8 nm) of the visible absorption maximum, and lack of a distinct UV absorption peak around 280 nm. The similarities between the absorption spectra of 1 in various acidic and neutral buffer solutions implied restricted formation of the instable colourless equilibrium forms, which are typical for most anthocyanins in weakly acidic solutions. The molar absorptivity (epsilon) of 1 varied little with pH contrary to similar values of for instance the major anthocyanin in strawberry, 2. However, 2 revealed higher epsilon-values than 1 at all pH values except 5.1. At pH 5.1, the epsilon-value of 1 (6250) was nearly four times the corresponding value of 2 (1720), which showed the potential of 5-carboxypyranopelargonidin derivatives as colorants in solutions with pH around 5. The colours of 1 and 2 in buffered solutions with pH 1.1 and pH 6.9 have been described by the CIELAB coordinates h(ab) (hue angle), C* (chroma), and L* (lightness).

  18. Study of flavonoids of Sechium edule (Jacq) Swartz (Cucurbitaceae) different edible organs by liquid chromatography photodiode array mass spectrometry.

    Science.gov (United States)

    Siciliano, Tiziana; De Tommasi, Nunziatina; Morelli, Ivano; Braca, Alessandra

    2004-10-20

    A liquid chromatography-mass spectrometry (LC-MS)-based method was developed for the characterization of flavonoids from Sechium edule (Jacq) Swartz (Cucurbitaceae) edible organs, a plant cultivated since pre-Colombian times in Mexico where the fruit is called chayote. Chayote is used for human consumption in many countries; in addition to the fruits, stems, leaves and the tuberous part of the roots are also eaten. Eight flavonoids, including three C-glycosyl and five O-glycosyl flavones, were detected, characterized by nuclear magnetic resonance spectroscopic data, and quantified in roots, leaves, stems, and fruits of the plant by LC-photodiode array-MS. The aglycone moieties are represented by apigenin and luteolin, while the sugar units are glucose, apiose, and rhamnose. The results indicated that the highest total amount of flavonoids was in the leaves (35.0 mg/10 g of dried part), followed by roots (30.5 mg/10 g), and finally by stems (19.3 mg/10 g). Copyright 2004 American Chemical Society

  19. Absorption, Conjugation and Efflux of the Flavonoids, Kaempferol and Galangin, Using the Intestinal CACO-2/TC7 Cell Model.

    Science.gov (United States)

    Barrington, Robert; Williamson, Gary; Bennett, Richard N; Davis, Barry D; Brodbelt, Jennifer S; Kroon, Paul A

    2009-01-01

    Flavonoids are biologically active compounds in food with potential health effects. We have used the Caco-2 cell monolayer model to study the absorption and metabolism of two flavonols, a class of flavonoids, specifically kaempferol and galangin. Metabolism experiments allowed identification of 5 kaempferol conjugates: 3-, 7- and 4'-glucuronide, a sulphate and a glucurono-sulphate; and 4 galangin conjugates: 3-, 5- and 7-glucuronides, and a sulphate, using specific enzyme hydrolysis, HPLC-MS, and HPLC with post column metal complexation/tandem MS. Transport studies showed that the flavonols were conjugated inside the cells then transported across the monolayer or effluxed back to the apical side. Sulphated conjugates were preferentially effluxed back to the apical side, whereas glucuronides were mostly transported to the basolateral side. For kaempferol, a small amount of the unconjugated aglycone permeated in both directions, indicating some passive diffusion. When kaempferol-3-glucuronide and quercetin7-sulphate were applied to either side of the cells, no permeation in either direction was observed, indicating that conjugates cannot re-cross the cell monolayer. Formation of apical kaempferol-7- and 4'-glucuronides was readily saturated, whereas formation of other conjugates at the apical side and all at the basolateral side increased with increasing concentration of kaempferol, implying different transporters are responsible at the apical and basolateral sides. The results highlight the important but complex metabolic changes occurring in flavonoids during absorption.

  20. Compositional changes in (iso)flavonoids and estrogenic activity of three edible Lupinus species by germination and Rhizopus-elicitation.

    Science.gov (United States)

    Aisyah, Siti; Vincken, Jean-Paul; Andini, Silvia; Mardiah, Zahara; Gruppen, Harry

    2016-02-01

    The effects of germination and elicitation on (iso)flavonoid composition of extracts from three edible lupine species (Lupinus luteus, Lupinus albus, Lupinus angustifolius) were determined by RP-UHPLC-MS(n). The total (iso)flavonoid content of lupine increased over 10-fold upon germination, with the total content and composition of isoflavonoids more affected than those of flavonoids. Glycosylated isoflavones were the most predominant compounds found in lupine seedlings. Lesser amounts of isoflavone aglycones, including prenylated ones, were also accumulated. Elicitation with Rhizopus oryzae, in addition to germination, raised the content of isoflavonoids further: the total content of 2'-hydroxygenistein derivatives was increased considerably, without increasing that of genistein derivatives. Elicitation by fungus triggered prenylation of isoflavonoids, especially of the 2'-hydroxygenistein derivatives. The preferred positions of prenylation differed among the three lupine species. The change in isoflavone composition increased the agonistic activity of the extracts towards the human estrogen receptors, whereas no antagonistic activity was observed. Copyright © 2015 Elsevier Ltd. All rights reserved.

  1. The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties.

    Science.gov (United States)

    Guo, Cheng; Hu, Min; DeOrazio, Russell J; Usyatinsky, Alexander; Fitzpatrick, Kevin; Zhang, Zhenjun; Maeng, Jun-Ho; Kitchen, Douglas B; Tom, Susan; Luche, Michele; Khmelnitsky, Yuri; Mhyre, Andrew J; Guzzo, Peter R; Liu, Shuang

    2014-07-01

    The sodium glucose co-transporter 2 (SGLT2) has received considerable attention in recent years as a target for the treatment of type 2 diabetes mellitus. This report describes the design, synthesis and structure-activity relationship (SAR) of C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties as novel SGLT2 inhibitors. Compounds 5p and 33b demonstrated high potency in inhibiting SGLT2 and high selectivity against SGLT1. The in vitro ADMET properties of these compounds will also be discussed. Copyright © 2014 Elsevier Ltd. All rights reserved.

  2. Delivering flavonoids into solid tumors using nanotechnologies.

    Science.gov (United States)

    Wang, Shengpeng; Zhang, Jinming; Chen, Meiwan; Wang, Yitao

    2013-10-01

    Long-term epidemiological studies have demonstrated that regular ingestion of flavonoids contained in dietary sources is associated with a reduced risk for many chronic diseases including cancer. However, although flavonoids are largely consumed in the diet and high concentrations may exist in the intestine after oral administration, the plasma/tissue concentrations of flavonoids are lower than their effective therapeutic doses due to poor bioavailability, resulting in the limited efficacy of flavonoids in various clinical studies. Therefore, the application of nanotechnology to deliver flavonoids to tumor sites has received considerable attention in recent years. In this review, after a general review of the potential benefits of flavonoids in cancer therapy and several key factors affecting their bioavailability, the current efforts in improving the delivery efficacy of promising candidates that are particularly important in the human diet, namely quercetin, epigallocatechin-3-gallate (EGCG) and genistein were focused on. Finally, the challenges of developing flavonoid delivery systems that improve flavonoid bioavailability and their anticancer therapy potentials were summarized. The design of suitable molecular carriers for flavonoids is an area of research that is in rapid progress. A large number of unheeded promising favonoids are suffering from poor in vivo parameters, their potential benefits deserves further research. Furthermore, more effort should be placed on developing active targeting systems, evaluating the efficacy and toxicity of novel flavonoid delivery systems through small and large scale clinical trials.

  3. Cancer chemoprevention through dietary flavonoids: what's limiting?

    Science.gov (United States)

    Amawi, Haneen; Ashby, Charles R; Tiwari, Amit K

    2017-06-19

    Flavonoids are polyphenols that are found in numerous edible plant species. Data obtained from preclinical and clinical studies suggest that specific flavonoids are chemo-preventive and cytotoxic against various cancers via a multitude of mechanisms. However, the clinical use of flavonoids is limited due to challenges associated with their effective use, including (1) the isolation and purification of flavonoids from their natural resources; (2) demonstration of the effects of flavonoids in reducing the risk of certain cancer, in tandem with the cost and time needed for epidemiological studies, and (3) numerous pharmacokinetic challenges (e.g., bioavailability, drug-drug interactions, and metabolic instability). Currently, numerous approaches are being used to surmount some of these challenges, thereby increasing the likelihood of flavonoids being used as chemo-preventive drugs in the clinic. In this review, we summarize the most important challenges and efforts that are being made to surmount these challenges.

  4. Flavonoid Bioavailability and Attempts for Bioavailability Enhancement

    Science.gov (United States)

    Thilakarathna, Surangi H.; Rupasinghe, H. P. Vasantha

    2013-01-01

    Flavonoids are a group of phytochemicals that have shown numerous health effects and have therefore been studied extensively. Of the six common food flavonoid classes, flavonols are distributed ubiquitously among different plant foods whereas appreciable amounts of isoflavones are found in leguminous plant-based foods. Flavonoids have shown promising health promoting effects in human cell culture, experimental animal and human clinical studies. They have shown antioxidant, hypocholesterolemic, anti-inflammatory effects as well as ability to modulate cell signaling and gene expression related disease development. Low bioavailability of flavonoids has been a concern as it can limit or even hinder their health effects. Therefore, attempts to improve their bioavailability in order to improve the efficacy of flavonoids are being studied. Further investigations on bioavailability are warranted as it is a determining factor for flavonoid biological activity. PMID:23989753

  5. Enrichment of two isoflavone aglycones in black soymilk by using spent coffee grounds as an immobiliser for β-glucosidase.

    Science.gov (United States)

    Chen, Kuan-I; Lo, Yi-Chen; Liu, Chia-Wei; Yu, Roch-Chui; Chou, Cheng-Chun; Cheng, Kuan-Chen

    2013-08-15

    Spent coffee grounds, discarded as environmental pollutants, were adopted as enzyme immobilisation solid carriers instead of commercialised solid supports to establish an economical catalytic system. β-Glucosidase was covalently immobilised onto spent coffee grounds for the conversion of isoflavone glycosides into their aglycones in black soymilk. Optimum conditions were determined to be 40°C and pH 6 using 4-nitrophenyl β-D-glucuronide as an indicator. Operational reusability was confirmed for more than 30 batch reactions and the storage stability was capable of sustaining its highest catalytic activity for 20 days. The kinetic parameters including rate constant (K), time (τ(50)) in which 50% of isoflavone deglycosylation was reached, and time (τ(complete)) required to achieve complete isoflavone deglycosylation, were 0.16±0.02 min(-1), 4.54±0.32 min, 60 min for daidzin and 0.16±0.02 min(-1), 2.28±0.11 min, 60 min for genistin, respectively. The total aglycone content in black soymilk was enriched by 67.14±0.60% in the enzymatic treatment of 60 min duration. Copyright © 2013 Elsevier Ltd. All rights reserved.

  6. Flavonoids: promising natural compounds against viral infections.

    Science.gov (United States)

    Zakaryan, Hovakim; Arabyan, Erik; Oo, Adrian; Zandi, Keivan

    2017-09-01

    Flavonoids are widely distributed as secondary metabolites produced by plants and play important roles in plant physiology, having a variety of potential biological benefits such as antioxidant, anti-inflammatory, anticancer, antibacterial, antifungal and antiviral activity. Different flavonoids have been investigated for their potential antiviral activities and several of them exhibited significant antiviral properties in in vitro and even in vivo studies. This review summarizes the evidence for antiviral activity of different flavonoids, highlighting, where investigated, the cellular and molecular mechanisms of action on viruses. We also present future perspectives on therapeutic applications of flavonoids against viral infections.

  7. Characterisation of proanthocyanidin aglycones and glycosides from rose hips by high-performance liquid chromatography-mass spectrometry, and their rapid quantification together with vitamin C.

    Science.gov (United States)

    Salminen, Juha-Pekka; Karonen, Maarit; Lempa, Kyösti; Liimatainen, Jaana; Sinkkonen, Jari; Lukkarinen, Marjo; Pihlaja, Kalevi

    2005-06-10

    Fifteen individual proanthocyanidin aglycones and 19 glycosides, together with a complex mixture of chromatographically non-separated tetra- to octameric proanthocyanidin glycosides were detected--the non-separated glycosides being novel natural products--and characterised from dog rose hips using high-performance liquid chromatography-electrospray ionisation mass spectrometry (HPLC-ESI-MS). Along with these phenolics, a 50% aqueous ethanol extract of rose hips was found to contain high levels of Vitamin C. A simple and rapid HPLC method assisted by diode array detection for the estimation of the total concentration of proanthocyanidin aglycones and glycosides, as well as Vitamin C, in rose hip extracts was developed.

  8. Recent Advances in the Catalytic One-Pot Synthesis of Flavonoids and Chromones.

    Science.gov (United States)

    Mohadeszadeh, Manijeh; Iranshahi, Mehrdad

    2017-01-01

    Flavonoids and chromones are two important classes of natural products that have various biological properties. During the past 10 years, there has been a significant increase in studies on the one-pot synthesis of flavonoids and chromones as medicinal scaffolds in drug discovery. This review describes the scope, mechanistic properties and regio- and chemo-selectivity features of several recently developed one-pot procedures for the synthesis of substituted chromones and flavonoids that have recently been published. Special importance is placed on the most promising and exciting medicinal applications of flavonoids and chromones. In this review, we discuss the progress on the synthesis of flavonoid and chromone derivatives in the presence of metal catalysts, organocatalysts, solid surfaces, microwave irradiation, acid and base catalysis, etc. For example, flavones can be prepared via the catalytic coordination of palladium complexes in a short time and at a low temperature with a high yield. Additionally, the one-pot synthesis of 2-substituted chromones via metal triflate (Yb(OTf)3) has provided the best result for this type of reaction with a high yield and a high regio and chemoselectivity. Generally, this review proposes the first specific overview of this developing and rapidly expanding field of flavonoid synthesis. We also discuss the mechanisms and advantages and disadvantages of methods for the synthesis of flavonoids and chromones. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  9. Investigation of metal–flavonoid chelates and the determination of flavonoids via metal–flavonoid complexing reactions

    Directory of Open Access Journals (Sweden)

    DUSAN MALESEV

    2007-10-01

    Full Text Available Flavonoids constitute a large group of polyphenolic phytochemicals with antioxidant properties which are overwhelmingly exerted through direct free radical scavenging. Flavonoids also exhibit antioxidant properties through chelating with transition metals, primarily Fe(II, Fe(III and Cu(II, which participate in reactions generating free radicals. Metal–flavonoid chelates are considerably more potent free radical scavengers than the parent flavonoids and play a prominent role in protecting from oxidative stress. To unravel the origin of their potent biological action extensive physico–chemical studies were undertaken to reveal the chemical structure, chelation sites, assess the impact of the metal/ligand ratio on the structure of the complexes and the capacity of flavonoids to bind metal ions. In spite of such extensive efforts, data on the composition, structure and complex-formation properties are incomplete and sometimes even contradictory. The aim of this paper is to give a personal account on the development of the field through a retrospective evaluation of our own research which covers approximately 40 complexes of flavonoids from different flavonoids subclasses (rutin, quercetin, 3-hydroxyflavone, morin and hesperidin with several metal ions or groups and suggest directions for future research. Special emphasis will be given to the site of the central ion, the composition of the complexes, the role of pH in complex formation, the stability of metal–flavonoid complexes and their potential application for analytical purposes.

  10. Wine Flavonoids in Health and Disease Prevention.

    Science.gov (United States)

    Fernandes, Iva; Pérez-Gregorio, Rosa; Soares, Susana; Mateus, Nuno; de Freitas, Victor

    2017-02-14

    Wine, and particularly red wine, is a beverage with a great chemical complexity that is in continuous evolution. Chemically, wine is a hydroalcoholic solution (~78% water) that comprises a wide variety of chemical components, including aldehydes, esters, ketones, lipids, minerals, organic acids, phenolics, soluble proteins, sugars and vitamins. Flavonoids constitute a major group of polyphenolic compounds which are directly associated with the organoleptic and health-promoting properties of red wine. However, due to the insufficient epidemiological and in vivo evidences on this subject, the presence of a high number of variables such as human age, metabolism, the presence of alcohol, the complex wine chemistry, and the wide array of in vivo biological effects of these compounds suggest that only cautious conclusions may be drawn from studies focusing on the direct effect of wine and any specific health issue. Nevertheless, there are several reports on the health protective properties of wine phenolics for several diseases such as cardiovascular diseases, some cancers, obesity, neurodegenerative diseases, diabetes, allergies and osteoporosis. The different interactions that wine flavonoids may have with key biological targets are crucial for some of these health-promoting effects. The interaction between some wine flavonoids and some specific enzymes are one example. The way wine flavonoids may be absorbed and metabolized could interfere with their bioavailability and therefore in their health-promoting effect. Hence, some reports have focused on flavonoids absorption, metabolism, microbiota effect and overall on flavonoids bioavailability. This review summarizes some of these major issues which are directly related to the potential health-promoting effects of wine flavonoids. Reports related to flavonoids and health highlight some relevant scientific information. However, there is still a gap between the knowledge of wine flavonoids bioavailability and their health

  11. Author Details

    African Journals Online (AJOL)

    Waterman, P.G.. Vol 6, No 2 (1992) - Articles Flavonoids of polygonum senegalense (MEISN) part II: More surface and internal tissue flavonoid aglycones. Abstract PDF · Vol 4, No 2 (1990) - Articles Anti-feedant effects of surface accumulated flavonoids of Polygonum Senegalense Abstract PDF. ISSN: 1726-801X.

  12. Metode Cepat Identifikasi Flavonoid dari Daun Ocimum sanctum L. (Selasih)

    OpenAIRE

    Diah Dhianawaty; Ramdan Panigoro; Samsudin Surialaga; Pricilla Purushothman

    2012-01-01

    A plant’s effectiveness as a herbal drug comes from its chemical content such as flavonoids. Flavonoids are useful for human body health. Therefore flavonoids content can be used as a marker from the usefulness of a plant, and rapid identification method of flavonoid is needed. The objective of the research was to get a rapid method of flavonoid content identification from Ocimum sanctum. The extraction, isolation and identification of flavonoids from Ocimum sanctum leaves has been done at Me...

  13. Dietary flavonoids: intake, health effects and bioavailability

    NARCIS (Netherlands)

    Hollman, P.C.H.; Katan, M.B.

    1999-01-01

    Flavonoids are polyphenolic compounds that occur ubiquitously in foods of plant origin. Over 4000 different flavonoids have been described. They may have beneficial health effects because of their antioxidant properties and their inhibitory role in various stages of tumour development in animal

  14. CYTOTOXIC FLAVONOIDS FROM ERYTHRINA CAFFRA THUNB ...

    African Journals Online (AJOL)

    . Its stem bark was investigated for the flavonoid constituents and biological activity. Some isolated flavonoids, 3, 5, 6, 8, 9, 10, 11,. 12, 13, 15 and 16 were found to be active against the human cervix carcinoma KB-3-1 cells with IC50 values in.

  15. Flavonoids--food sources and health benefits.

    Science.gov (United States)

    Kozłowska, Aleksandra; Szostak-Wegierek, Dorota

    2014-01-01

    Flavonoids are a group of bioactive compounds that are extensively found in foodstuffs of plant origin. Their regular consumption is associated with reduced risk of a number of chronic diseases, including cancer, cardiovascular disease (CVD) and neurodegenerative disorders. Flavonoids are classified into subgroups based on their chemical structure: flavanones, flavones, flavonols, flavan-3-ols, anthocyanins and isoflavones. Their actions at the molecular level include antioxidant effects, as well the ability to modulate several key enzymatic pathways. The growing body of scientific evidence indicates that flavonoids play a beneficial role in disease prevention, however further clinical and epidemiological trials are greatly needed. Among dietary sources of flavonoids there are fruits, vegetables, nuts, seeds and spices. Consumption of these substances with diet appears to be safe. It seems that a diet rich in flavonoids is beneficial and its promotion is thus justifiable.

  16. Subcritical ethanol extraction of flavonoids from Moringa oleifera leaf and evaluation of antioxidant activity.

    Science.gov (United States)

    Wang, Yongqiang; Gao, Yujie; Ding, Hui; Liu, Shejiang; Han, Xu; Gui, Jianzhou; Liu, Dan

    2017-03-01

    A large-scale process to extract flavonoids from Moringa oleifera leaf by subcritical ethanol was developed and HPLC-MS analysis was conducted to qualitatively identify the compounds in the extracts. To optimize the effects of process parameters on the yield of flavonoids, a Box-Behnken design combined with response surface methodology was conducted in the present work. The results indicated that the highest extraction yield of flavonoids by subcritical ethanol extraction could reach 2.60% using 70% ethanol at 126.6°C for 2.05h extraction. Under the optimized conditions, flavonoids yield was substantially improved by 26.7% compared with the traditional ethanol reflux method while the extraction time was only 2h, and obvious energy saving was observed. FRAP and DPPH assays showed that the extracts had strong antioxidant and free radical scavenging activities. Copyright © 2016 Elsevier Ltd. All rights reserved.

  17. Excretion of the urinary 5C- and 7C-aglycone metabolites of vitamin K by young adults responds to changes in dietary phylloquinone and dihydrophylloquinone intakes.

    Science.gov (United States)

    Harrington, Dominic J; Booth, Sarah L; Card, David J; Shearer, Martin J

    2007-07-01

    The physiological function and putative health roles of vitamin K-dependent proteins now extend beyond their classical role in hemostasis and include bone mineralization, arterial calcification, apoptosis, phagocytosis, growth control, chemotaxis, and signal transduction. Current assessments of vitamin K status do not reflect the variety of molecular forms of vitamin K. We assessed whether urinary excretion of 2-methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-naphthoquinone (7C-aglycone) and 2-methyl-3-(3'-3'-carboxymethylpropyl)-1,4-naphthoquinone (5C-aglycone), vitamin K metabolites common to both phylloquinone and the menaquinone series, reflect dietary vitamin K intake. In a randomized crossover study, 9 adults resided in a metabolic unit for two 30-d periods separated by a free-living period of > or = 4 wk. During each residency, subjects consumed 3 sequential diets: a control diet (93 microg phylloquinone/d) for 5 d, a phylloquinone-restricted diet (11 microg/d) for 15 d, followed by a randomly assigned repletion diet for 10 d with either phylloquinone (206 microg/d) or dihydrophylloquinone (240 microg/d). During the second residency, the alternative repletion diet was assigned. Urinary excretion of the 5C- and 7C-aglycones was measured in sequential 24-h collections. The 5C-aglycone accounted for approximately 75% of total excretion and declined in response to phylloquinone restriction (P = 0.001) to approximately 30% of that during the control diet period. Repletion with phylloquinone and dihydrophylloquinone doubled the excretion rate of the major 5C-aglycone by 24 h (P < 0.001), and tripled excretion by 4 d. There was a linear relationship between the logarithm of total urinary excretion and dietary vitamin K intake (r = 0.699, P < 0.001). We conclude that the urinary excretion of vitamin K metabolites reflects dietary phylloquinone intake and offers the first candidate marker of global vitamin K status.

  18. Ten-year comparison of the influence of organic and conventional crop management practices on the content of flavonoids in tomatoes.

    Science.gov (United States)

    Mitchell, Alyson E; Hong, Yun-Jeong; Koh, Eunmi; Barrett, Diane M; Bryant, D E; Denison, R Ford; Kaffka, Stephen

    2007-07-25

    Understanding how environment, crop management, and other factors, particularly soil fertility, influence the composition and quality of food crops is necessary for the production of high-quality nutritious foods. The flavonoid aglycones quercetin and kaempferol were measured in dried tomato samples (Lycopersicon esculentum L. cv. Halley 3155) that had been archived over the period from 1994 to 2004 from the Long-Term Research on Agricultural Systems project (LTRAS) at the University of California-Davis, which began in 1993. Conventional and organic processing tomato production systems are part of the set of systems compared at LTRAS. Comparisons of analyses of archived samples from conventional and organic production systems demonstrated statistically higher levels (P tomatoes. Ten-year mean levels of quercetin and kaempferol in organic tomatoes [115.5 and 63.3 mg g(-1) of dry matter (DM)] were 79 and 97% higher than those in conventional tomatoes (64.6 and 32.06 mg g(-1) of DM), respectively. The levels of flavonoids increased over time in samples from organic treatments, whereas the levels of flavonoids did not vary significantly in conventional treatments. This increase corresponds not only with increasing amounts of soil organic matter accumulating in organic plots but also with reduced manure application rates once soils in the organic systems had reached equilibrium levels of organic matter. Well-quantified changes in tomato nutrients over years in organic farming systems have not been reported previously.

  19. Zinc oxide crystal whiskers as a novel sorbent for solid-phase extraction of flavonoids.

    Science.gov (United States)

    Wang, Licheng; Shangguan, Yangnan; Hou, Xiudan; Jia, Yong; Liu, Shujuan; Sun, Yingxin; Guo, Yong

    2017-08-15

    As a novel solid-phase extraction material, zinc oxide crystal whiskers were used to extract flavonoid compounds and showed good extraction abilities. X-ray diffraction, scanning electron microscopy with energy dispersive X-ray spectroscopy and surface area/pore volume characterized the sorbent. The zinc oxide was packed into a solid-phase extraction micro-column and its extraction ability was evaluated by four model flavonoid compounds. The sample loading and elution parameters were optimized and the zinc oxide based analytical method for flavonoids was established. It showed that the method has wide linearities from 1 to 150μg/L and low limits of detection at 0.25μg/L. The relative standard deviations of a single column repeatability and column to column reproducibility were less than 6.8% and 10.6%. Several real samples were analyzed by the established method and satisfactory results were obtained. The interactions between flavonoids and zinc oxide were calculated and proved to be from the Van der Waals' forces between the 4p and 5d orbitals from zinc atom and the neighboring π orbitals from flavonoid phenyl groups. Moreover, the zinc oxide crystal whiskers showed good stability and could be reused more than 50 times under the operation conditions. This work proves that the zinc oxide crystal whiskers are a good candidate for flavonoids enrichment. Copyright © 2017. Published by Elsevier B.V.

  20. Structure-cytotoxicity relationships for dietary flavonoids

    DEFF Research Database (Denmark)

    Breinholt, V.; Dragsted, L.O.

    1998-01-01

    The cytotoxicity of a large series of dietary flavonoids was tested in a non-tumorigenic mouse and two human cancer cell lines, using the neutral red dye exclusion assay. All compounds tested exhibited a concentration-dependent cytotoxic action in the employed cell lines. The relative cytotoxicity...... of the flavonoids, however, Tvas found to vary greatly among the different cell Lines. With a few exceptions, the investigated flavonoids were more cytotoxic to the human cancer cell lines, than the mouse cell line. The differences in cytotoxicity were accounted for in part by differences in cellular uptake...... and metabolic capacity among the different cell types. In 3T3 cells fairly consistent structure-cytotoxicity relationships were found. The most cytotoxic structures tested in 3T3 cells were flavonoids with adjacent 3',4' hydroxy groups on the B-ring, such as luteolin, quercetin, myricetin, fisetin, eriodictyol...

  1. Flavonoids as scavengers of nitric oxide radical.

    NARCIS (Netherlands)

    van Acker, S.A.B.E.; Tromp, M.N.J.L.; Haenen, G.R.M.M.; van der Vijgh, W.J.F.; Bast, A.

    1995-01-01

    Flavonoids are a group of naturally occurring compounds used, e.g., in the treatment of vascular endothelial damage. They are known to be excellent scavengers of oxygen free radicals. Since the nitric oxide radical (

  2. Structure-cytotoxicity relationships for dietary flavonoids

    DEFF Research Database (Denmark)

    Breinholt, V.; Dragsted, L.O.

    1998-01-01

    , and taxifolin. The structural requirements for cytotoxicity in the human cell lines, however, were less clear. Reduction of the cytotoxic response of the 3',4'-hydroxylated flavonoid, quercetin, by the hydroxyl radical scavenger mannitol and the metal chelator desferozamine suggests that reactive oxygen species......The cytotoxicity of a large series of dietary flavonoids was tested in a non-tumorigenic mouse and two human cancer cell lines, using the neutral red dye exclusion assay. All compounds tested exhibited a concentration-dependent cytotoxic action in the employed cell lines. The relative cytotoxicity...... of the flavonoids, however, Tvas found to vary greatly among the different cell Lines. With a few exceptions, the investigated flavonoids were more cytotoxic to the human cancer cell lines, than the mouse cell line. The differences in cytotoxicity were accounted for in part by differences in cellular uptake...

  3. Wine Flavonoids in Health and Disease Prevention

    Directory of Open Access Journals (Sweden)

    Iva Fernandes

    2017-02-01

    Full Text Available Wine, and particularly red wine, is a beverage with a great chemical complexity that is in continuous evolution. Chemically, wine is a hydroalcoholic solution (~78% water that comprises a wide variety of chemical components, including aldehydes, esters, ketones, lipids, minerals, organic acids, phenolics, soluble proteins, sugars and vitamins. Flavonoids constitute a major group of polyphenolic compounds which are directly associated with the organoleptic and health-promoting properties of red wine. However, due to the insufficient epidemiological and in vivo evidences on this subject, the presence of a high number of variables such as human age, metabolism, the presence of alcohol, the complex wine chemistry, and the wide array of in vivo biological effects of these compounds suggest that only cautious conclusions may be drawn from studies focusing on the direct effect of wine and any specific health issue. Nevertheless, there are several reports on the health protective properties of wine phenolics for several diseases such as cardiovascular diseases, some cancers, obesity, neurodegenerative diseases, diabetes, allergies and osteoporosis. The different interactions that wine flavonoids may have with key biological targets are crucial for some of these health-promoting effects. The interaction between some wine flavonoids and some specific enzymes are one example. The way wine flavonoids may be absorbed and metabolized could interfere with their bioavailability and therefore in their health-promoting effect. Hence, some reports have focused on flavonoids absorption, metabolism, microbiota effect and overall on flavonoids bioavailability. This review summarizes some of these major issues which are directly related to the potential health-promoting effects of wine flavonoids. Reports related to flavonoids and health highlight some relevant scientific information. However, there is still a gap between the knowledge of wine flavonoids

  4. Antioxidant flavonoids bind human serum albumin

    Science.gov (United States)

    Kanakis, C. D.; Tarantilis, P. A.; Polissiou, M. G.; Diamantoglou, S.; Tajmir-Riahi, H. A.

    2006-10-01

    Human serum albumin (HSA) is a principal extracellular protein with a high concentration in blood plasma and carrier for many drugs to different molecular targets. Flavonoids are powerful antioxidants and prevent DNA damage. The antioxidative protections are related to their binding modes to DNA duplex and complexation with free radicals in vivo. However, flavonoids are known to inhibit the activities of several enzymes such as calcium phospholipid-dependent protein kinase, tyrosine protein kinase from rat lung, phosphorylase kinase, phosphatidylinositol 3-kinase and DNA topoisomerases that exhibit the importance of flavonoid-protein interaction. This study was designed to examine the interaction of human serum albumin (HSA) with quercetin (que), kaempferol (kae) and delphinidin (del) in aqueous solution at physiological conditions, using constant protein concentration of 0.25 mM (final) and various drug contents of 1 μM-1 mM. FTIR and UV-vis spectroscopic methods were used to determine the polyphenolic binding mode, the binding constant and the effects of flavonoid complexation on protein secondary structure. The spectroscopic results showed that flavonoids are located along the polypeptide chains through H-bonding interactions with overall affinity constant of Kque = 1.4 × 10 4 M -1, Kkae = 2.6 × 10 5 M -1 and Kdel = 4.71 × 10 5 M -1. The protein secondary structure showed no alterations at low pigment concentration (1 μM), whereas at high flavonoid content (1 mM), major reduction of α-helix from 55% (free HSA) to 42-46% and increase of β-sheet from 15% (free HSA) to 17-19% and β-anti from 7% (free HSA) to 10-20% occurred in the flavonoid-HSA adducts. The major reduction of HSA α-helix is indicative of a partial protein unfolding upon flavonoid interaction.

  5. SERS study of riboflavin on green-synthesized silver nanoparticles prepared by reduction using different flavonoids: What is the role of flavonoid used?

    Science.gov (United States)

    Švecová, Marie; Ulbrich, Pavel; Dendisová, Marcela; Matějka, Pavel

    2018-04-01

    Spectroscopy of surface-enhanced Raman scattering (SERS) is nowadays widely used in the field of bio-science and medicine. These applications require new enhancing substrates with special properties. They should be non-toxic, environmentally friendly and (bio-) compatible with examined samples. Flavonoids are natural antioxidants with many positive effects on human health. Simultaneously, they can be used as reducing agent in preparation procedure of plasmonic enhancing substrate for SERS spectroscopy. The best amplifiers of Raman vibrational spectroscopic signal are generally silver nanoparticles (AgNPs). In this study, several flavonoids (forming a logical set) were used as reducing agent in AgNPs preparation procedures. Reactivity of 10 structurally arranged flavonoids (namely flavone, chrysin, apigenin, luteolin, tricetin, 3-hydroxyflavone, galangin, kaempferol, quercetin and myricetin) was compared and SERS-activity of prepared AgNPs was tested using model analyte riboflavin. Riboflavin was detected down to concentration 10-9 mol/l.

  6. Flavonoids and oxidative stress in Drosophila melanogaster.

    Science.gov (United States)

    Sotibrán, América Nitxin Castañeda; Ordaz-Téllez, María Guadalupe; Rodríguez-Arnaiz, Rosario

    2011-11-27

    Flavonoids are a family of antioxidants that are widely represented in fruits, vegetables, dry legumes, and chocolate, as well as in popular beverages, such as red wine, coffee, and tea. The flavonoids chlorogenic acid, kaempferol, quercetin and quercetin 3β-d-glycoside were investigated for genotoxicity using the wing somatic mutation and recombination test (SMART). This test makes use of two recessive wing cell markers: multiple wing hairs (mwh) and flare (flr(3)), which are mutations located on the left arm of chromosome 3 of Drosophila melanogaster and are indicative of both mitotic recombination and various types of mutational events. In order to test the antioxidant capacities of the flavonoids, experiments were conducted with various combinations of oxidants and polyphenols. Oxidative stress was induced using hydrogen peroxide, the Fenton reaction and paraquat. Third-instar transheterozygous larvae were chronically treated for all experiments. The data obtained in this study showed that, at the concentrations tested, the flavonoids did not induce somatic mutations or recombination in D. melanogaster with the exception of quercetin, which proved to be genotoxic at only one concentration. The oxidants hydrogen peroxide and the Fenton reaction did not induce mutations in the wing somatic assay of D. melanogaster, while paraquat and combinations of flavonoids produced significant numbers of small single spots. Quercetin 3β-d-glycoside mixed with paraquat was shown to be desmutagenic. Combinations of the oxidants with the other flavonoids did not show any antioxidant activity. Copyright © 2011 Elsevier B.V. All rights reserved.

  7. Leaf surface lipophilic compounds as one of the factors of silver birch chemical defense against larvae of gypsy moth.

    Directory of Open Access Journals (Sweden)

    Vyacheslav V Martemyanov

    Full Text Available Plant chemical defense against herbivores is a complex process which involves a number of secondary compounds. It is known that the concentration of leaf surface lipophilic compounds (SLCs, particularly those of flavonoid aglycones are increased with the defoliation treatment of silver birch Betula pendula. In this study we investigated how the alteration of SLCs concentration in the food affects the fitness and innate immunity of the gypsy moth Lymantria dispar. We found that a low SLCs concentrations in consumed leaves led to a rapid larval development and increased females' pupae weight (= fecundity compared to larvae fed with leaves with high SLCs content. Inversely, increasing the compounds concentration in an artificial diet produced the reverse effects: decreases in both larval weight and larval survival. Low SLCs concentrations in tree leaves differently affected larval innate immunity parameters. For both sexes, total hemocytes count in the hemolymph increased, while the activity of plasma phenoloxidase decreased when larvae consume leaves with reduced content of SLCs. Our results clearly demonstrate that the concentration of SLCs in silver birch leaves affects not only gypsy moth fitness but also their innate immune status which might alter the potential resistance of insects against infections and/or parasitoids.

  8. Quantitative measurement of major secoiridoid derivatives in olive oil using qNMR. Proof of the artificial formation of aldehydic oleuropein and ligstroside aglycon isomers.

    Science.gov (United States)

    Karkoula, Evangelia; Skantzari, Angeliki; Melliou, Eleni; Magiatis, Prokopios

    2014-01-22

    A previously developed method for measurement of oleocanthal and oleacein in olive oil by quantitative (1)H NMR was expanded to include the measurement of the monoaldehydic forms of oleuropein and ligstroside aglycons. The method was validated and applied to the study of 340 monovarietal Greek and Californian olive oils from 23 varieties and for a 3-year period. A wide variation concerning the concentrations of all four secoiridoids was recorded. The concentration of each one ranged from nondetectable to 711 mg/kg and the sum of the four major secoiridoids (named as D3) ranged from nondetectable to 1534 mg/kg. Examination of the NMR profile of the olive oil extract before and after contact with normal or reversed stationary chromatography phase proved the artificial formation of the 5S,8S,9S aldehydic forms of oleuropein and ligstroside aglycon isomers during chromatography. Finally, methyl elenolate was identified for the first time as a minor constituent of olive oil.

  9. Flavonoids, Flavonoid Subclasses, and Esophageal Cancer Risk: A Meta-Analysis of Epidemiologic Studies.

    Science.gov (United States)

    Cui, Lingling; Liu, Xinxin; Tian, Yalan; Xie, Chen; Li, Qianwen; Cui, Han; Sun, Changqing

    2016-06-08

    Flavonoids have been suggested to play a chemopreventive role in carcinogenesis. However, the epidemiologic studies assessing dietary intake of flavonoids and esophageal cancer risk have yielded inconsistent results. This study was designed to examine the association between flavonoids, each flavonoid subclass, and the risk of esophageal cancer with a meta-analysis approach. We searched for all relevant studies with a prospective cohort or case-control study design published from January 1990 to April 2016, using PUBMED, EMBASE, and Web of Science. Pooled odds ratios (ORs) were calculated using fixed or random-effect models. In total, seven articles including 2629 cases and 481,193 non-cases were selected for the meta-analysis. Comparing the highest-intake patients with the lowest-intake patients for total flavonoids and for each flavonoid subclass, we found that anthocyanidins (OR = 0.60, 95% CI: 0.49-0.74), flavanones (OR = 0.65, 95% CI: 0.49-0.86), and flavones (OR = 0.78, 95% CI 0.64-0.95) were inversely associated with the risk of esophageal cancer. However, total flavonoids showed marginal association with esophageal cancer risk (OR = 0.78, 95% CI: 0.59-1.04). In conclusion, our study suggested that dietary intake of total flavonoids, anthocyanidins, flavanones, and flavones might reduce the risk of esophageal cancer.

  10. Oleuropein aglycone protects transgenic C. elegans strains expressing Aβ42 by reducing plaque load and motor deficit.

    Directory of Open Access Journals (Sweden)

    Luisa Diomede

    Full Text Available The presence of amyloid aggregates of the 42 amino acid peptide of amyloid beta (Aβ42 in the brain is the characteristic feature of Alzheimer's disease (AD. Amyloid beta (Aβ deposition is also found in muscle fibers of individuals affected by inclusion body myositis (sIBM, a rare muscular degenerative disease affecting people over 50. Both conditions are presently lacking an effective therapeutic treatment. There is increasing evidence to suggest that natural polyphenols may prevent the formation of toxic amyloid aggregates; this applies also to oleuropein aglycone (OLE, the most abundant polyphenol in extra virgin olive oil, previously shown to hinder amylin and Aβ aggregation. Here we evaluated the ability of OLE to interfere with Aβ proteotoxicity in vivo by using the transgenic CL2006 and CL4176 strains of Caenorhabditis elegans, simplified models of AD and of sIBM, which express human Aβ in the cytoplasm of body wall muscle cells. OLE-fed CL2006 worms displayed reduced Aβ plaque deposition, less abundant toxic Aβ oligomers, remarkably decreased paralysis and increased lifespan with respect to untreated animals. A protective effect was also observed in CL4176 worms but only when OLE was administered before the induction of the Aβ transgene expression. These effects were specific, dose-related, and not mediated by the known polyphenolic anti-oxidant activity, suggesting that, in this model organism, OLE interferes with the Aβ aggregation skipping the appearance of toxic species, as already shown in vitro for Aβ42.

  11. Oleuropein Aglycone Protects against MAO-A-Induced Autophagy Impairment and Cardiomyocyte Death through Activation of TFEB

    Directory of Open Access Journals (Sweden)

    Caterina Miceli

    2018-01-01

    Full Text Available Age-associated diseases such as neurodegenerative and cardiovascular disorders are characterized by increased oxidative stress associated with autophagy dysfunction. Oleuropein aglycone (OA, the main polyphenol found in olive oil, was recently characterized as an autophagy inducer and a promising agent against neurodegeneration. It is presently unknown whether OA can have beneficial effects in a model of cardiac stress characterized by autophagy dysfunction. Here, we explored the effects of OA in cardiomyocytes with overexpression of monoamine oxidase-A (MAO-A. This enzyme, by degrading catecholamine and serotonin, produces hydrogen peroxide (H2O2, which causes oxidative stress, autophagic flux blockade, and cell necrosis. We observed that OA treatment counteracted the cytotoxic effects of MAO-A through autophagy activation, as displayed by the increase of autophagic vacuoles and autophagy-specific markers (Beclin1 and LC3-II. Moreover, the decrease in autophagosomes and the increase in autolysosomes, indicative of autophagosome-lysosome fusion, suggested a restoration of the defective autophagic flux. Most interestingly, we found that the ability of OA to confer cardioprotection through autophagy induction involved nuclear translocation and activation of the transcriptional factor EB (TFEB. Our data provide strong evidence of the beneficial effects of OA, suggesting its potential use as a nutraceutical agent against age-related pathologies involving autophagy dysfunction, including cardiovascular diseases.

  12. Biotransformation of lignan glycoside to its aglycone by Woodfordia fruticosa flowers: quantification of compounds using a validated HPTLC method.

    Science.gov (United States)

    Mishra, Shikha; Aeri, Vidhu

    2017-12-01

    Saraca asoca Linn. (Caesalpiniaceae) is an important traditional remedy for gynaecological disorders and it contains lyoniside, an aryl tetralin lignan glycoside. The aglycone of lyoniside, lyoniresinol possesses structural similarity to enterolignan precursors which are established phytoestrogens. This work illustrates biotransformation of lyoniside to lyoniresinol using Woodfordia fruticosa Kurz. (Lythraceae) flowers and simultaneous quantification of lyoniside and lyoniresinol using a validated HPTLC method. The aqueous extract prepared from S. asoca bark was fermented using W. fruticosa flowers. The substrate and fermented product both were simultaneously analyzed using solvent system:toluene:ethyl acetate:formic acid (4:3:0.4) at 254 nm. The method was validated for specificity, accuracy, precision, linearity, sensitivity and robustness as per ICH guidelines. The substrate showed the presence of lyoniside, however, it decreased as the fermentation proceeded. On 3rd day, lyoniresinol starts appearing in the medium. In 8 days duration most of the lyoniside converted to lyoniresinol. The developed method was specific for lyoniside and lyoniresinol. Lyoniside and lyoniresinol showed linearity in the range of 250-3000 and 500-2500 ng. The method was accurate as resulted in 99.84% and 99.83% recovery, respectively, for lyoniside and lyoniresinol. Aryl tetralin lignan glycoside, lyoniside was successfully transformed into lyoniresinol using W. fruticosa flowers and their contents were simultaneously analyzed using developed validated HPTLC method.

  13. The Role of Flavonoids as Potential Radioprotectors

    International Nuclear Information System (INIS)

    Benkovic, V.; Djikic, D.; Horvat Knezevic, A.; Lisicic, D.; Orsolic, N.; Kopjar, N.

    2011-01-01

    Investigations for effective and non toxic compounds with radioprotection capability led to increasing interest in naturally occurring antioxidants since most of known chemical radioprotectors (AET, WR2721, WR 1065, etc.) express toxic side effects that limit their use in medical practice. Among the promissing compounds there are flavonoids, whosentioxidant activity is based on ability of direct free radicals scavenging or stabilizing the reactive oxygen species (ROS) by interacting with the reactive compound of the radical. Because of the high reactivity of the hydroxyl substituents of flavonoids, radicals are made inactive. Flavonoids can also increase the function of the endogenous antioxidant enzyme systems: superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx), glutathione reductase (GR) and gluthation. Antioxidant effects may be also a combined result of radical scavenging and interaction with enzyme functions. Flavonoids induce activities of the immune system as well. Increased hematopoietic activity could account for the improved hematopoietic tolerance to radiotherapy. In this study we evaluated radioprotective effects of selected flavonoids (caffeic acid, chrysin, naringin and quercetin) administered to mice prior to whole-body irradiation with γ-rays (absorbed dose was 9 Gy). The survival analysis and alkaline comet assay on white blood cells were employed both on irradiated and non-irradiated animals. Blood samples were taken 30 min. after irradiation. Appropriate negative and positive control groups (administered chemical radioprotector AET, S-(2-Aminoethyl) isothiouronium bromide hydrobromide, i. p. at a dose of 281 mg kg -1 body weight) were also selected and handled in the same manner. We observed statistically significant difference in surviving time of mice pre-treated with test components and the most effective radioprotector was quercetin. Tested flavonoids were not genotoxic to non-irradiated mice and offered good

  14. 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 2 O 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

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

    Energy Technology Data Exchange (ETDEWEB)

    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

  16. Flavonoids from leaves of Mauritia flexuosa

    Directory of Open Access Journals (Sweden)

    Djalma M. de Oliveira

    2013-09-01

    Full Text Available The chromatographic fractionation of the Mauritia flexuosa L. f., Arecaceae, leaves extract, a plant known by the name of buriti palm tree, resulted in the isolation of six flavonoids: tricin-7-O-rutinoside, apigenin-6-C-arabinoside, 8-C-glucoside (isoschaftoside, kaempferol-3-O-rutinoside (nicotiflorine, quercetin-3-O-rutinoside (rutin, luteolin-8-C-glucoside (orientin and luteolin-6-C-glucoside (isoorientin. The flavonoids were found out and previously reported as constituents of the Arecaceae family plants, but the occurrence of C-glucoside flavonoids, in the species being analyzed, is described for the first time on this study. The structural elucidations of all of the isolated compounds were performed by means of the comparison of their spectral data (¹H and 13C NMR, UV and ESI-MS with those ones of the literature.

  17. Flavonoids in Inflammatory Bowel Disease: A Review

    Science.gov (United States)

    Vezza, Teresa; Rodríguez-Nogales, Alba; Algieri, Francesca; Utrilla, Maria Pilar; Rodriguez-Cabezas, Maria Elena; Galvez, Julio

    2016-01-01

    Inflammatory bowel disease (IBD) is characterized by chronic inflammation of the intestine that compromises the patients’ life quality and requires sustained pharmacological and surgical treatments. Since their etiology is not completely understood, non-fully-efficient drugs have been developed and those that have shown effectiveness are not devoid of quite important adverse effects that impair their long-term use. In this regard, a growing body of evidence confirms the health benefits of flavonoids. Flavonoids are compounds with low molecular weight that are widely distributed throughout the vegetable kingdom, including in edible plants. They may be of great utility in conditions of acute or chronic intestinal inflammation through different mechanisms including protection against oxidative stress, and preservation of epithelial barrier function and immunomodulatory properties in the gut. In this review we have revised the main flavonoid classes that have been assessed in different experimental models of colitis as well as the proposed mechanisms that support their beneficial effects. PMID:27070642

  18. Flavonoids as fruit and vegetable intake biomarkers

    DEFF Research Database (Denmark)

    Krogholm, Kirstine Suszkiewicz

    of fruit and vegetable intake (Nielsen et al. 2002). The overall aim of the present Ph.D. thesis was to further develop and validate this potentially new fruit and vegetable biomarker and furthermore use it for the validation of self-reported dietary intake of fruits and vegetables in intervention...... and cohort studies. The Ph.D. thesis contains four scientific papers. Paper I provides evidence that the sum of 7 flavonoids in 24h urine respond in a linear and sensitive manner to moderate increases in the intake of fruits and vegetables, and thus consolidates that the flavonoids are a valid biomarker...... of fruit and vegetable intakes. In Paper I, the urinary recovery of the 7 flavonoids in morning spot urine (i.e. all urine voids from midnight including the first morning void) was also found to respond to moderate increases in the intake of fruits and vegetables. However, the association was somewhat...

  19. Voltammetric Detection of Antioxidative Properties of Flavonoids Using Electrically Heated DNA Modified Carbon Paste Electrode

    Directory of Open Access Journals (Sweden)

    P. Gründler

    2003-01-01

    Full Text Available A simple electrochemical sensor consisting of electrically heated carbon paste electrode with the surface modified by dsDNA is used to characterize voltammetric behaviour and antioxidative activity of four selected flavonoids. Quercetin, rutin, catechin and epigallocatechin gallate accumulate within the DNA layer. A positive effect of the electrode temperature within the range of 20 to 38 ºC on the detection of a deep DNA degradation by a copper(II/H2O2/ascorbic acid cleavage mixture as well as an antioxidative effect of flavonoids was evaluated.

  20. Association of flavonoid-rich foods and flavonoids with risk of all-cause mortality.

    Science.gov (United States)

    Ivey, Kerry L; Jensen, Majken K; Hodgson, Jonathan M; Eliassen, A Heather; Cassidy, Aedín; Rimm, Eric B

    2017-05-01

    Flavonoids are bioactive compounds found in foods such as tea, red wine, fruits and vegetables. Higher intakes of specific flavonoids, and flavonoid-rich foods, have been linked to reduced mortality from specific vascular diseases and cancers. However, the importance of flavonoid-rich foods, and flavonoids, in preventing all-cause mortality remains uncertain. As such, we examined the association of intake of flavonoid-rich foods and flavonoids with subsequent mortality among 93 145 young and middle-aged women in the Nurses' Health Study II. During 1 838 946 person-years of follow-up, 1808 participants died. When compared with non-consumers, frequent consumers of red wine, tea, peppers, blueberries and strawberries were at reduced risk of all-cause mortality (Pflavonoid intake were at reduced risk of all-cause mortality in the age-adjusted model; 0·81 (95 % CI 0·71, 0·93). However, this association was attenuated following multivariable adjustment; 0·92 (95 % CI 0·80, 1·06). Similar results were observed for consumption of flavan-3-ols, proanthocyanidins and anthocyanins. Flavonols, flavanones and flavones were not associated with all-cause mortality in any model. Despite null associations at the compound level and select foods, higher consumption of red wine, tea, peppers, blueberries and strawberries, was associated with reduced risk of total and cause-specific mortality. These findings support the rationale for making food-based dietary recommendations.

  1. Flavonoids – Small Molecules, High Hopes

    Directory of Open Access Journals (Sweden)

    Sandu Mariana

    2017-07-01

    Full Text Available This brief review takes a look at flavonoids, a wide class of polyphenols, which are regarded as plant secondary metabolites. Their roles in plants are diverse and little understood. They can act as growth hormone modulators, phytoalexins, they offer UV protection, contribute to pollen viability and can function as signaling molecules in establishing symbiotic relationships. Flavonoids were also found to have a range of beneficial effects for the human body. Their anticancer, antioxidant, anti-inflammatory and cardioprotective activity, as well as their antibacterial, antiviral and antihelmintic properties make them promising candidates for the design of new drugs.

  2. Flavonoids and terpenoids from Croton muscicarpa (Euphorbiaceae)

    International Nuclear Information System (INIS)

    Barreto, Milena B.; Gomes, Clêrton L.; Freitas, João Vito B. de; Pinto, Francisco das Chagas L.; Silveira, Edilberto R.; Gramosa, Nilce V.; Torres, Daniela S. Carneiro

    2013-01-01

    A new sesquiterpene and twelve known compounds comprising eight flavonoids and four terpenoids, were isolated from the leaves, stems, roots and exudate of Croton muscicarpa Müll.. Arg.. Their structures were identified as the terpenoids 6α-methoxy-cyperene, dammaradienol, squalene, acetyl aleuritolic acid and spathulenol, and as the flavonoids retusin, 3,7,4’-trimethoxy kaempferol, ombuine, pachipodol, kaempferol, casticin, 5-hydroxy-3,6,7,4’-tetramethoxyflavone and artemetin. All isolated compounds were characterized based on IR, MS, 1 H and 13 C NMR, including 2D analyses (COSY, HSQC, HMBC, NOESY) and comparison with data from the literature. (author)

  3. Flavonoides e terpenoides de Croton muscicarpa (Euphorbiaceae

    Directory of Open Access Journals (Sweden)

    Milena B. Barreto

    2013-01-01

    Full Text Available A new sesquiterpene and twelve known compounds comprising eight flavonoids and four terpenoids, were isolated from the leaves, stems, roots and exudate of Croton muscicarpa Müll. Arg.. Their structures were identified as the terpenoids 6α-methoxy-cyperene, dammaradienol, squalene, acetyl aleuritolic acid and spathulenol, and as the flavonoids retusin, 3,7,4'-trimethoxy kaempferol, ombuine, pachipodol, kaempferol, casticin, 5-hydroxy-3,6,7,4'-tetramethoxyflavone and artemetin. All isolated compounds were characterized based on IR, MS, ¹H and 13C NMR, including 2D analyses (COSY, HSQC, HMBC, NOESY and comparison with data from the literature.

  4. [Study on Flavonoids in Buddleja lindleyana Fruits].

    Science.gov (United States)

    Yu, Hao; Ren, Ya-shuo; Wu, De-ling; Xu, Feng-qing; Zhang, Wei

    2015-04-01

    To study the flavonoids in the fruits of Buddleja lindleyana. The compounds were separated by repeated silica gel, RP-18 and Sephadex LH-20. Their structures were elucidated on the basis of chemical evidence and spectral data. Five flavonoids were isolated and identified as luteolin (1), tricin (2), acacetin (3), acacetin-7-O-β-D-glucopyranoside (4) and linarin(5). Compounds 3,4 and 5 are isolated from fruits of Buddleja lindleyana for the first time. Compound 2 is isolated from fruits of Buddleja lindleyana for the first time.

  5. Flavonoids and terpenoids from Croton muscicarpa (Euphorbiaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Barreto, Milena B.; Gomes, Clerton L.; Freitas, Joao Vito B. de; Pinto, Francisco das Chagas L.; Silveira, Edilberto R.; Gramosa, Nilce V., E-mail: nilce@dqoi.ufc.br [Departamento de Quimica Organica e Inorganica, Centro de Ciencias, Universidade Federal do Ceara, Fortaleza (Brazil); Torres, Daniela S. Carneiro [Departamento de Ciencias Biologicas Jequie, Universidade Estadual do Sudoeste da Bahia, Jequie, BA (Brazil)

    2013-09-01

    A new sesquiterpene and twelve known compounds comprising eight flavonoids and four terpenoids, were isolated from the leaves, stems, roots and exudate of Croton muscicarpa Muell.. Arg.. Their structures were identified as the terpenoids 6{alpha}-methoxy-cyperene, dammaradienol, squalene, acetyl aleuritolic acid and spathulenol, and as the flavonoids retusin, 3,7,4'-trimethoxy kaempferol, ombuine, pachipodol, kaempferol, casticin, 5-hydroxy-3,6,7,4'-tetramethoxyflavone and artemetin. All isolated compounds were characterized based on IR, MS, {sup 1}H and {sup 13}C NMR, including 2D analyses (COSY, HSQC, HMBC, NOESY) and comparison with data from the literature. (author)

  6. Exploring the aglycone subsite of a GH11 xylanase for the synthesis of xylosides by transglycosylation reactions.

    Science.gov (United States)

    Brusa, C; Belloy, N; Gérard, D; Muzard, M; Dauchez, M; Plantier-Royon, R; Rémond, C

    2018-03-01

    Xylanases Tx-xyn10 and Tx-xyn11 were compared for their transxylosylation abilities in the presence of various acceptors. Tx-xyn10 exhibited a broad specificity for various acceptors, whereas xylanase Tx-xyn11 catalysed transxylosylation reactions only in presence of polyphenolic acceptors. A modelling approach was developed to study the molecular bottlenecks into the active site of the enzyme that could be responsible for this restricted specificity. The glycosyl-enzyme intermediate of Tx-xyn11 was modelled, and a rotamer of the Y78 residue was integrated. In silico mutations of some residues from the (+1) and (+2) subsites were tested for the deglycosylation step in the presence of non-polyphenolic acceptors. The results indicated that the mutant W126A was able to use aliphatic alcohols and benzyl alcohol as acceptors for transxylosylation. Experimental validation was tested by mutating the xylanase Tx-xyn11 at position W126 into alanine. The specific activity and catalytic efficiency of the W126A mutant during the hydrolysis of xylans decreased by 2-fold and 4-fold, respectively, compared to wild-type xylanase. Among tested acceptors, transxylosylation catalysed by mutant W126A was improved with benzyl alcohol leading to a 2-fold higher concentration of benzyl xylobioside, as predicted by in silico mutation. This improved transxylosylation in the presence of benzyl alcohol leading to higher synthesis of benzyl xylobioside could likely be explained by lowest steric hindrance in the aglycone subsite of the mutated xylanase. No secondary hydrolysis of benzyl xylobioside occurred for both wild-type and mutant xylanases. Finally, our results demonstrated that the modelling approach was limited and that accounting for protein dynamics can lead to improved models. Copyright © 2018. Published by Elsevier B.V.

  7. Strains for the production of flavonoids from glucose

    Energy Technology Data Exchange (ETDEWEB)

    Stephanopoulos, Gregory; Santos, Christine; Koffas, Mattheos

    2015-11-13

    The invention relates to the production of flavonoids and flavonoid precursors in cells through recombinant expression of tyrosine ammonia lyase (TAL), 4-coumarate:CoA ligase (4CL), chalcone synthase (CHS), and chalcone isomerase (CHI).

  8. Cranberry Flavonoids Modulate Cariogenic Properties of Mixed-Species Biofilm through Exopolysaccharides-Matrix Disruption.

    Science.gov (United States)

    Kim, Dongyeop; Hwang, Geelsu; Liu, Yuan; Wang, Yifei; Singh, Ajay P; Vorsa, Nicholi; Koo, Hyun

    2015-01-01

    The exopolysaccharides (EPS) produced by Streptococcus mutans-derived glucosyltransferases (Gtfs) are essential virulence factors associated with the initiation of cariogenic biofilms. EPS forms the core of the biofilm matrix-scaffold, providing mechanical stability while facilitating the creation of localized acidic microenvironments. Cranberry flavonoids, such as A-type proanthocyanidins (PACs) and myricetin, have been shown to inhibit the activity of Gtfs and EPS-mediated bacterial adhesion without killing the organisms. Here, we investigated whether a combination of cranberry flavonoids disrupts EPS accumulation and S. mutans survival using a mixed-species biofilm model under cariogenic conditions. We also assessed the impact of cranberry flavonoids on mechanical stability and the in situ pH at the biofilm-apatite interface. Topical application of an optimized combination of PACs oligomers (100-300 μM) with myricetin (2 mM) twice daily was used to simulate treatment regimen experienced clinically. Treatments with cranberry flavonoids effectively reduced the insoluble EPS content (>80% reduction vs. vehicle-control; pcranberry-treated biofilms was severely compromised, showing a defective EPS-matrix and failure to develop microcolonies on the saliva-coated hydroxyapatite (sHA) surface. Furthermore, topical applications of cranberry flavonoids significantly weaken the mechanical stability of the biofilms; nearly 90% of the biofilm was removed from sHA surface after exposure to a shear stress of 0.449 N/m2 (vs. 36% removal in vehicle-treated biofilms). Importantly, in situ pH measurements in cranberry-treated biofilms showed significantly higher pH values (5.2 ± 0.1) at the biofilm-apatite interface vs. vehicle-treated biofilms (4.6 ± 0.1). Altogether, the data provide important insights on how cranberry flavonoids treatments modulate virulence properties by disrupting the biochemical and ecological changes associated with cariogenic biofilm development, which

  9. Purification of Flavonoids from Black Currant Juice by Nanodiafiltration

    DEFF Research Database (Denmark)

    Jensen, Morten Busch; Christensen, Knud Villy; Norddahl, Birgir

    2009-01-01

      Various compounds of the flavonoid group have been reported to possess therapeutic effects towards cancer [1]. Thus there is a large potential in identifying, purifying and quantifying flavonoids from different natural sources in order to screen the pharmaceutical values of these. The flavonoid...

  10. Estrogenicity and metabolism of prenylated flavonoids and isoflavonoids

    NARCIS (Netherlands)

    Schans, van de M.G.M.

    2015-01-01

      Binding of (prenylated) flavonoids and isoflavonoids to the human estrogen receptors (hERs) might result in beneficial health effects in vivo. To understand structure-activity relationships of prenylated (iso)flavonoids towards the hERs, prenylated (iso)flavonoids were purified from extracts

  11. THE SYSTEMATIC AND EVOLUTIONARY SIGNIFICANCE OF EXUDATE FLAVONOIDS IN AEONIUM

    NARCIS (Netherlands)

    STEVENS, JF; HART, HT; WOLLENWEBER, E

    Leaf exudates of 32 species of Aeonium were examined for the presence of flavonoids. Thirty two flavonoids were detected in exudates of half of the species. The flavonoids were identified as methyl ethers of kaempferol, 6-hydroxykaempferol, quercetin, myricetin and scutellarein. The distribution of

  12. Genotypic variation in tree growth and selected flavonoids in leaves ...

    African Journals Online (AJOL)

    Growth and flavonoid content varied significantly among different families, and isoquercitrin was the main component of the individual flavonoids, followed by kaempferol and quercetin. Both total and individual flavonoids showed seasonal variation, with the mean highest contents of quercetin and isoquercitrin in July but the ...

  13. Absorption, metabolism and health effects of dietary flavonoids in man.

    NARCIS (Netherlands)

    Hollman, P.C.H.; Katan, M.B.

    1997-01-01

    Flavonoids are polyphenolic compounds that occur ubiquitously in foods of plant origin. Over 4,000 different flavonoids have been described, and they are categorized into flavonols, flavones, catechins, flavanones, anthocyanidins and isoflavonoids. Flavonoids have a variety of biological effects in

  14. Flavonoids protecting food and beverages against light.

    Science.gov (United States)

    Huvaere, Kevin; Skibsted, Leif H

    2015-01-01

    Flavonoids, which are ubiquitously present in the plant kingdom, preserve food and beverages at the parts per million level with minor perturbation of sensory impressions. Additionally, they are safe and possibly contribute positive health effects. Flavonoids should be further exploited for the protection of food and beverages against light-induced quality deterioration through: (1) direct absorption of photons as inner filters protecting sensitive food components; (2) deactivation of (triplet-)excited states of sensitisers like chlorophyll and riboflavin; (3) quenching of singlet oxygen from type II photosensitisation; and (iv) scavenging of radicals formed as reaction intermediates in type I photosensitisation. For absorption of light, combinations of flavonoids, as found in natural co-pigmentation, facilitate dissipation of photon energy to heat thus averting photodegradation. For protection against singlet oxygen and triplet sensitisers, chemical quenching gradually decreases efficiency hence the pathway to physical quenching should be optimised through product formulation. The feasibility of these protection strategies is further supported by kinetic data that are becoming available, allowing for calculation of threshold levels of flavonoids to prevent beer and dairy products from going off. On the other hand, increasing understanding of the interplay between light and matrix physicochemistry, for example the effect of aprotic microenvironments on phototautomerisation of compounds like quercetin, opens up for engineering better light-to-heat converting channels in processed food to eventually prevent quality loss. © 2014 Society of Chemical Industry.

  15. Antidepressant screening and flavonoids isolation from ...

    African Journals Online (AJOL)

    Eremostachys laciniata (L) Bunge (Lamiaceae), a rich source of flavonoids, has been investigated for chemical constituents and in vivo antidepressant property using forced swim test (FST) model. Five important compounds were isolated, including luteolin (1), apigenin (2), 5,8-dihydroxy-6,7- dimethoxyflavone (3), 5 ...

  16. Flavonoids and platelet aggregation: A brief review.

    Science.gov (United States)

    Faggio, Caterina; Sureda, Antoni; Morabito, Silvia; Sanches-Silva, Ana; Mocan, Andrei; Nabavi, Seyed Fazel; Nabavi, Seyed Mohammad

    2017-07-15

    Platelets are small anucleated fragments derived from a megakaryocyte precursor. Platelets play a key role in many physiological functions especially in hemostasis and wound healing processes in order to maintain the integrity of the circulatory system. In addition, activated platelets release cytokines and chemokines which modulate the immune response and, in some cases of hyperactivation, they could be associated to the pathogenesis of inflammatory diseases. Flavonoids are polyphenolic compounds ubiquosly found in plants known to be potent antioxidants with positive effects against diverse diseases such as cancer, neurodegenerative or cardiovascular disease. It has been reported that some flavonoids possess anti-platelet aggregation effects though different pathways, being the inhibition of the arachidonic acid-based pathway the most representative mechanism of action. In the present review, the main sources of flavonoids, as well as their bioavailability and metabolism are summarized. Moreover, the available data about the anti-aggregation effects of flavonoids and the different mechanisms of action that has been proposed until now are also discussed. Copyright © 2017 Elsevier B.V. All rights reserved.

  17. 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 ...

  18. Effects of flavonoids on cognitive performance

    Science.gov (United States)

    Recent studies suggest that nutritional interventions, such as increasing dietary intake of fruits and vegetables, could possibly delay and even reverse age-related declines in brain function such as cognitive and motor performance. Fruits and vegetables rich in flavonoids play a critical role in pr...

  19. Antiplasmodial and larvicidal flavonoids from Derris trifoliata

    African Journals Online (AJOL)

    Preferred Customer

    ABSTRACT. ABSTRACT. From the dichloromethane-methanol (1:1) extract of the seed pods of Derris trifoliata, a new flavanone derivative (S)-lupinifolin 4´-methyl ether was isolated. In addition, the known flavonoids lupinifolin and rotenone were identified. The structures were determined on the basis of spectroscopic ...

  20. Flavonoids and volatiles in Chrysanthemum morifolium Ramat ...

    African Journals Online (AJOL)

    USER

    2010-06-21

    Jun 21, 2010 ... China, was purchased from market, ground using a EUPA TSK-. 927S grinder ... HPLC analysis of flavonoids and their derivatives. The HPLC were ..... Ye Q, Liang YR, Lu JH (2007). Effect of different extracting methods on quality of Chrysanthemum morifolium Ramat infusion. Asia Pacific J. Clin. Nutr.

  1. Differential accumulation of flavonoids by tomato (Solanum ...

    African Journals Online (AJOL)

    SARAH

    2014-12-29

    Dec 29, 2014 ... Student – Newman – Keuls Test was used to compare means differences. In some few cases where .... extension of their shelf-life by delaying over ripening and reducing susceptibility to Botrytis cinerea. However ... 2001. Flavonoids act as negative regulators of auxin transport in vivo in Arabidopsis. Plant.

  2. Antimicrobial action of purified raspberry flavonoid

    African Journals Online (AJOL)

    user

    2012-02-07

    Feb 7, 2012 ... Optimization of conditions for supercritical fluid extraction of flavonoids from hops (Humulus lupulus L.). J. Zhejiang Univ. Sci. 6: 999-1004. Herrera MC. Luque de Castro MD (2005). Ultraviolet-assisted extraction of phenolic compounds from strawberries prior to liquid chromatographic separation and ...

  3. Antiplasmodial and larvicidal flavonoids from Derris trifoliata ...

    African Journals Online (AJOL)

    From the dichloromethane-methanol (1:1) extract of the seed pods of Derris trifoliata, a new flavanone derivative (S)-lupinifolin 4´-methyl ether was isolated. In addition, the known flavonoids lupinifolin and rotenone were identified. The structures were determined on the basis of spectroscopic evidence. Lupinfolin showed ...

  4. Pectolinarigenin - A Flavonoid Compound from Cirsium Japonicum ...

    African Journals Online (AJOL)

    HP

    /tjpr.v13i2.9. Original Research Article. Pectolinarigenin - A Flavonoid Compound from Cirsium. Japonicum with Potential Anti-proliferation Activity in MCF-. 7 Breast Cancer Cell. Mingqian Lu. 1,2,3. , Qingzhi Kong. 1,4. *, Xinhua Xu. 2,3.

  5. Flavonoids of Calligonum polygonoides and their cytotoxicity.

    Science.gov (United States)

    Ahmed, Hayam; Moawad, Abeer; Owis, Asmaa; AbouZid, Sameh; Ahmed, Osama

    2016-10-01

    Context Calligonum polygonoides L. subsp. comosum L' Hér. (Polygonaceae), locally known as "arta", is a slow-growing small leafless desert shrub. Objective Isolation, structure elucidation and evaluation of cytotoxic activity of flavonoids from C. polygonoides aerial parts. Materials and methods Flavonoids in the hydroalcoholic extract of the of C. polygonoides were isolated and purified using column chromatography and preparative HPLC. The structures of the isolated flavonoids were elucidated on the basis of spectroscopic data including 2D NMR techniques. The cytotoxic activity of the isolated flavonoids (6.25, 25, 50 and 100 μg/mL) was evaluated against liver HepG2 and breast MCF-7 cancer cell lines using sulphorhodamine-B assay. Results A new flavonoid, kaempferol-3-O-β-D-(6″-n-butyl glucuronide) (1), and 13 known flavonoids, quercetin 3-O-β-D-(6″-n-butyl glucuronide) (2), kaempferol-3-O-β-D-(6″-methyl glucuronide) (3), quercetin-3-O-β-D-(6″-methyl glucuronide) (4), quercetin-3-O-glucuronide (5), kaempferol-3-O-glucuronide (6), quercetin-3-O-α-rhamnopyranoside (7), astragalin (8), quercetin-3-O-glucopyranoside (9), taxifolin (10), (+)-catechin (11), dehydrodicatechin A (12), quercetin (13), and kaempferol (14), were isolated from the aerial parts of C. polygonoides. Quercetin showed significant cytotoxic activity against HepG2 and MCF-7 cell lines with IC50 values of 4.88 and 0.87 μg/mL, respectively. Structure-activity relationships were analyzed by comparing IC50 values of several pairs of flavonoids differing in one structural element. Discussion and conclusion The activity against breast cancer cell lines decreased by glycosylation at C-3. The presence of 2,3-double bond in ring C, carbonyl group at C-4 and 3',4'-dihydroxy substituents in ring B are essential structural requirements for the cytotoxic activity against breast cancer cells.

  6. Association among Dietary Flavonoids, Flavonoid Subclasses and Ovarian Cancer Risk: A Meta-Analysis

    Science.gov (United States)

    You, Ruxu; Yang, Yu; Liao, Jing; Chen, Dongsheng; Yu, Lixiu

    2016-01-01

    Background Previous studies have indicated that intake of dietary flavonoids or flavonoid subclasses is associated with the ovarian cancer risk, but presented controversial results. Therefore, we conducted a meta-analysis to derive a more precise estimation of these associations. Methods We performed a search in PubMed, Google Scholar and ISI Web of Science from their inception to April 25, 2015 to select studies on the association among dietary flavonoids, flavonoid subclasses and ovarian cancer risk. The information was extracted by two independent authors. We assessed the heterogeneity, sensitivity, publication bias and quality of the articles. A random-effects model was used to calculate the pooled risk estimates. Results Five cohort studies and seven case-control studies were included in the final meta-analysis. We observed that intake of dietary flavonoids can decrease ovarian cancer risk, which was demonstrated by pooled RR (RR = 0.82, 95% CI = 0.68–0.98). In a subgroup analysis by flavonoid subtypes, the ovarian cancer risk was also decreased for isoflavones (RR = 0.67, 95% CI = 0.50–0.92) and flavonols (RR = 0.68, 95% CI = 0.58–0.80). While there was no compelling evidence that consumption of flavones (RR = 0.86, 95% CI = 0.71–1.03) could decrease ovarian cancer risk, which revealed part sources of heterogeneity. The sensitivity analysis indicated stable results, and no publication bias was observed based on the results of Funnel plot analysis and Egger’s test (p = 0.26). Conclusions This meta-analysis suggested that consumption of dietary flavonoids and subtypes (isoflavones, flavonols) has a protective effect against ovarian cancer with a reduced risk of ovarian cancer except for flavones consumption. Nevertheless, further investigations on a larger population covering more flavonoid subclasses are warranted. PMID:26960146

  7. Flavonoids and heart health: Proceedings of the ILSI North America Flavonoids Workshop may 31-june 1, 2005, Washington DC

    NARCIS (Netherlands)

    Erdman, J.W.; Balentine, D.; Arab, L.; Beecher, G.; Dwyer, J.T.; Folts, J.; Harnly, J.; Hollman, P.C.H.; Keen, C.L.; Mazza, G.; Messina, M.; Scalbert, A.; Vita, J.; Williamson, G.; Burrows, J.

    2007-01-01

    This article provides an overview of current research on flavonoids as presented during a workshop entitled, "Flavonoids and Heart Health," held by the ILSI North America Project Committee on Flavonoids in Washington, DC, May 31 and June 1, 2005. Because a thorough knowledge and understanding about

  8. 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

    Directory of Open Access Journals (Sweden)

    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.

  9. A novel Aspergillus oryzae diglycosidase that hydrolyzes 6-O-α-L-rhamnosyl-β-D-glucoside from flavonoids.

    Science.gov (United States)

    Ishikawa, Mai; Kawasaki, Mayu; Shiono, Yoshihito; Koseki, Takuya

    2018-04-01

    α-L-Rhamnosyl-β-D-glucosidase (rutinosidase) hydrolyzes the glycosidic linkage between the disaccharide 6-O-α-L-rhamnosyl-β-D-glucoside (rutinose) and the aglycone. We identified a hypothetical protein (annotated as AO090012000917) encoded in the Aspergillus oryzae genome that exhibits sequence similarity with Aspergillus niger rutinosidase. The recombinant enzyme was expressed in Pichia pastoris GS115 and purified as a glyco-protein with apparent molecular mass of 65-75 kDa by SDS-PAGE. After N-deglycosylation, we observed a 42- and 40-kDa band, representing proteins before and after N-terminal signal peptide processing, respectively. Optimal enzymatic activity was observed at pH 4.0 and temperature of 45 °C. This enzyme is also significantly thermo-stable, with 90% activity retained after 1 h at 45 °C and 70% activity retained after 4 h, even at 50 °C. Biochemical characterization revealed that the enzyme has higher substrate specificity for 3-O-linked flavonoid β-rutinosides like rutin and kaempferol-3-O-rutinoside, than for 7-O-linked flavonoid β-rutinoside like hesperidin. However, no activity was found with naringin, diosmin, monoglycosylated chromogenic substrates, and polymeric laminarin substrate. Kinetic analyses showed that K m value toward rutin was higher than those toward hesperidin and kaempferol-3-O-rutinoside. Meanwhile, k cat value toward hesperidin was lower than those toward kaempferol-3-O-rutinoside and rutin. Overall, the catalytic efficiency (k cat /K m ) was highest for kaempferol-3-O-rutinoside.

  10. Metode Cepat Identifikasi Flavonoid dari Daun Ocimum sanctum L. (Selasih

    Directory of Open Access Journals (Sweden)

    Diah Dhianawaty

    2012-03-01

    Full Text Available A plant’s effectiveness as a herbal drug comes from its chemical content such as flavonoids. Flavonoids are useful for human body health. Therefore flavonoids content can be used as a marker from the usefulness of a plant, and rapid identification method of flavonoid is needed. The objective of the research was to get a rapid method of flavonoid content identification from Ocimum sanctum. The extraction, isolation and identification of flavonoids from Ocimum sanctum leaves has been done at Medical Chemistry laboratory Faculty of Medicine Universitas Padjadjaran in 2005. Flavonoids were extracted continually by 95% ethanol, were isolated with paper chromatography/cellulose TLC and 2% acetic acid, then continued with elucidation reagents: n-butanol–acetic acid–water, chloroform–acetic acid–water, forestall, 5%, 15%, 35% and 50% acetic acids. Flavonoids were identified with diagnostic reagents and ultraviolet light. Isolation with 2% and 35% acetic acids respectively gave two spots of flavonoids as flavon, FOAc-1 had Rf=0.69 and FOAc-2 had Rf=0.57. The other elucidation reagents gave one spot of flavonoid. In conclusion, isolation with 2% and 35% acetic acids respectively and identification with diagnostic reagent and ultraviolet light is a rapid method for identification of flavonoids content in Ocimum sanctum

  11. 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...... epidemiological studies but the evidence is inconclusive. One major obstacle for epidemiological studies investigating associations between flavonoid intake and risk of CHD is the estimation of flavonoid intake. There is a vast variety of flavonoids in commonly eaten food products but only limited knowledge...... 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...

  12. Natural Flavonoids as Promising Analgesic Candidates: A Systematic Review.

    Science.gov (United States)

    Xiao, Xiao; Wang, Xiaoyu; Gui, Xuan; Chen, Lu; Huang, Baokang

    2016-11-01

    Due to the chemical structural diversity and various analgesic mechanisms, an increasing number of studies indicated that some flavonoids from medicinal plants could be promising candidates for new natural analgesic drugs, which attract high interests of advanced users and academic researchers. The aim of this systematic review is to report flavonoids and its derivatives as new analgesic candidates based on the pharmacological evidences. Sixty-four papers were found concerning the potential analgesic activity of 46 flavonoids. In this case, the evidence for analgesic activity of flavonoids and total flavonoids was investigated. Meanwhile, the corresponding analgesic mechanism of flavonoids was discussed by generalizing and analyzing the current publications. Based on this review, the conclusion can be drawn that some flavonoids are promising candidates for painful conditions and deserve particular attention in further research and development. © 2016 Wiley-VHCA AG, Zurich, Switzerland.

  13. Genetic diversity of flavonoid content in leaf of hawthorn resources

    International Nuclear Information System (INIS)

    Zhao, Y.; Wang, G.; Liu, Z.

    2014-01-01

    Hawthorn (Cratageus spp.) are important medicinal plants. Flavonoids are the main active ingredient in hawthorn. With the help of hawthorn leaf flavonoids efficient detection system, vitexin, rhamnosylvitexin, hyperin, rutin and quercetin of 122 hawthorn resources was precisely measured.The flavonoid contents of 10 hawthorn species were explicited. The comparation of flavonoids revealed the abundant genetic diversity of hawthorn flavones. Large variable coefficient has been observed among 5 flavonoid monomer traits. The coefficients of variation were 44.17%, 132.2%, 157.08%, 113.91% and 31.05 for Vitexin, Rhamnosylvitexin, Hyperoside, Rutin and Quercetin respectively. The sum of these 5 flavonoid monomer contents represented the total flavonoids in hawthorn. The total coefficients of variation was 44.01%. Some high-content-flavone and valuable leaf resources were found. This research could provide accurate date for further production, breeding and the effective use of medicinal resources. (author)

  14. Supercritical Carbon Dioxide Extraction of Flavonoids from Pomelo (Citrus grandis (L.) Osbeck) Peel and Their Antioxidant Activity

    Science.gov (United States)

    He, Jin-Zhe; Shao, Ping; Liu, Jian-Hua; Ru, Qiao-Mei

    2012-01-01

    Supercritical carbon dioxide (SC-CO2) extraction of flavonoids from pomelo (Citrus grandis (L.) Osbeck) peel and their antioxidant activity were investigated. Box-Behnken design combined with response surface methodology was employed to maximize the extraction yield of flavonoids. Correlation analysis of the mathematical-regression model indicated that a quadratic polynomial model could be used to optimize the SC-CO2 extraction of flavonoids. The optimal conditions for obtaining the highest extraction yield of flavonoids from pomelo peel were a temperature of 80 °C, a pressure of 39 MPa and a static extraction time of 49 min in the presence of 85% ethanol as modifier. Under these conditions, the experimental yield was 2.37%, which matched positively with the value predicted by the model. Furthermore, flavonoids obtained by SC-CO2 extraction showed a higher scavenging activity on hydroxyl, 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals than those obtained by conventional solvent extraction (CSE). Therefore, SC-CO2 extraction can be considered as a suitable technique for the obtainment of flavonoids from pomelo peel. PMID:23202938

  15. Triterpenoids and flavonoids from celery (Apium graveolens).

    Science.gov (United States)

    Zhou, Kailan; Zhao, Feng; Liu, Zhihui; Zhuang, Yulei; Chen, Lixia; Qiu, Feng

    2009-09-01

    Three new triterpenoids, 11,21-dioxo-2beta,3beta,15alpha-trihydroxyurs-12-ene-2-O-beta-D-glucopyranoside (1), 11,21-dioxo-3beta,15alpha,24-trihydroxyurs-12-ene-24-O-beta-D-glucopyranoside (2), and 11,21-dioxo-3beta,15alpha,24-trihydroxyolean-12-ene-24-O-beta-D-glucopyranoside (3), and two new flavonoids, apigenin-7-O-[2''-O-(5'''-O-feruloyl)-beta-D-apiofuranosyl]-beta-D-glucopyranoside (4) and chrysoeriol-7-O-[2''-O-(5'''-O-feruloyl)-beta-D-apiofuranosyl]-beta-d-glucopyranoside (5), were isolated from the whole plant of fresh celery (Apium graveolens), together with 10 known flavonoids. The structures of the new compounds were elucidated by analysis of spectroscopic data. The inhibitory effects of the compounds isolated on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated.

  16. Flavonoids: from cell cycle regulation to biotechnology.

    Science.gov (United States)

    Woo, Ho-Hyung; Jeong, Byeong Ryong; Hawes, Martha C

    2005-03-01

    Flavonoids have been proposed to play diverse roles in plant growth and development, including defense, symbiosis, pollen development and male fertility, polar auxin transport, and protection against ultraviolet radiation. Recently, a new role in cell cycle regulation has emerged. Genetic alteration of glucuronide metabolism by altered expression of a Pisum sativum UDP-glucuronosyltransferase (PsUGT1) results in an altered cell cycle in pea, alfalfa, and Arabidopsis. In alfalfa, altered expression of PsUGT1 results in accumulation of a flavonoid-like compound that suppresses growth of cultured cells. The results are consistent with the hypothesis that PsUGT1 functions by controlling cellular levels of a factor controlling cell cycle (FCC).

  17. Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation.

    Science.gov (United States)

    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.

  18. Flavonoides e sesquiterpenos de Croton pedicellatus Kunth

    OpenAIRE

    Lopes, Elton Luz; Andrade Neto, Manoel; Silveira, Edilberto Rocha; Pessoa, Otilia Deusdênia Loiola; Braz-Filho, Raimundo

    2012-01-01

    The chemical investigation of the ethanolic extract from leaves of Croton pedicellatus yielded the bis-nor-sesquiterpenes blumenol A and blumenol A glucoside, along with the flavonoids: tiliroside, 6"-O-p-coumaroyl-β-galactopyranosyl- kaempferol, 6"-O-p-coumaroyl-β-glucopyranosyl-3"-methoxy- kaempferol, kaempferol, 3-glucopyranosyl-quercetin and alpinumisoflavone, as well as 4-hydroxy-3,5-dimethoxybenzoic acid. The identification of all isolated compounds was performed by spectrometric method...

  19. Tocopherols and flavonoids of SOS-7 halophyte

    Directory of Open Access Journals (Sweden)

    El-Shami, S. M.

    1993-10-01

    Full Text Available Halophyte is an oil seed coded as SOS-7 (Salicomia Oil Seed, 7th year of selection. Tocopherol constituents of SOS-7 halophyte oil were determined directly in the oil by using high pressure liquid chromatography coupled to fluorescence detector. It was found that the oil contains 710 ppm total tocopherols. The tocopherol constituents, alpha, beta, gamma and delta, were found at the level of 38.2,1.0, 58.7 and 2.1% respectively. Nine flavonoid glycosides were isolated and identified from the seeds and it was found that they belong to the flavonol class of flavonoids. These flavonol compounds were identified as: quercetin-3, 7-diglucoside, quercetin-3-glucoside-7-galactoside, quercetin-3-sophoroside, quercetin-3-glucoside, quercetin-3-galactoside, isorhamnetin-3, 7-di-glucoside, isorhamnetin-3-glucoside, kaempferol-3, 7-diglucoside and kaempferol-3-glucoside.

    Halofito es una semilla oleaginosa codificada como SOS-7 (semilla oleaginosa Salicomia, séptimo año de selección. Los tocoferoles del aceite de halofito SOS-7 fueron determinados directamente en el aceite usando cromatografía líquida de alta presión acoplada a detector fluorescente. Se encontró que el aceite contenía 710 ppm de tocoferoles totales. Los tocoferoles alfa, beta, gamma y delta, se encontraron a niveles de 38.2,1.0, 58.7 y 2.1%, respectivamente. Nueve glicósidos flavonoides fueron aislados e identificados de las semillas y se encontró que pertenecen a la clase flavonol dentro de los flavonoides. Estos flavonoles fueron identificados como: quercetina-3,7-diglucosido, quercetina-3-glucosido-7-galactosido, quercetina-3-soforosido, quercetina- 3-glucosido, quercetina-3-galactosido, isorannetina-3, 7-di-glucosido, isorannetina-3-glucosido, kampferol-3, 7-diglucosido y kampferol-3-glucosido.

  20. Enhancing Human Cognition with Cocoa Flavonoids

    OpenAIRE

    Valentina Socci; Daniela Tempesta; Giovambattista Desideri; Luigi De Gennaro; Michele Ferrara

    2017-01-01

    Enhancing cognitive abilities has become a fascinating scientific challenge, recently driven by the interest in preventing age-related cognitive decline and sustaining normal cognitive performance in response to cognitively demanding environments. In recent years, cocoa and cocoa-derived products, as a rich source of flavonoids, mainly the flavanols sub-class, have been clearly shown to exert cardiovascular benefits. More recently, neuromodulation and neuroprotective actions have been also su...

  1. Activity-Based Profiling of a Physiologic Aglycone Library Reveals Sugar Acceptor Promiscuity of Family 1 UDP-Glucosyltransferases from Grape1[W

    Science.gov (United States)

    Bönisch, Friedericke; Frotscher, Johanna; Stanitzek, Sarah; Rühl, Ernst; Wüst, Matthias; Bitz, Oliver; Schwab, Wilfried

    2014-01-01

    Monoterpenols serve various biological functions and accumulate in grape (Vitis vinifera), where a major fraction occurs as nonvolatile glycosides. We have screened the grape genome for sequences with similarity to terpene URIDINE DIPHOSPHATE GLYCOSYLTRANSFERASES (UGTs) from Arabidopsis (Arabidopsis thaliana). A ripening-related expression pattern was shown for three candidates by spatial and temporal expression analyses in five grape cultivars. Transcript accumulation correlated with the production of monoterpenyl β-d-glucosides in grape exocarp during ripening and was low in vegetative tissue. Targeted functional screening of the recombinant UGTs for their biological substrates was performed by activity-based metabolite profiling (ABMP) employing a physiologic library of aglycones built from glycosides isolated from grape. This approach led to the identification of two UDP-glucose:monoterpenol β-d-glucosyltransferases. Whereas VvGT14a glucosylated geraniol, R,S-citronellol, and nerol with similar efficiency, the three allelic forms VvGT15a, VvGT15b, and VvGT15c preferred geraniol over nerol. Kinetic resolution of R,S-citronellol and R,S-linalool was shown for VvGT15a and VvGT14a, respectively. ABMP revealed geraniol as the major biological substrate but also disclosed that these UGTs may add to the production of further glycoconjugates in planta. ABMP of aglycone libraries provides a versatile tool to uncover novel biologically relevant substrates of small-molecule glycosyltransferases that often show broad sugar acceptor promiscuity. PMID:25073706

  2. Chemistry and Biological Activities of Flavonoids: An Overview

    Science.gov (United States)

    Kumar, Shashank; Pandey, Abhay K.

    2013-01-01

    There has been increasing interest in the research on flavonoids from plant sources because of their versatile health benefits reported in various epidemiological studies. Since flavonoids are directly associated with human dietary ingredients and health, there is need to evaluate structure and function relationship. The bioavailability, metabolism, and biological activity of flavonoids depend upon the configuration, total number of hydroxyl groups, and substitution of functional groups about their nuclear structure. Fruits and vegetables are the main dietary sources of flavonoids for humans, along with tea and wine. Most recent researches have focused on the health aspects of flavonoids for humans. Many flavonoids are shown to have antioxidative activity, free radical scavenging capacity, coronary heart disease prevention, hepatoprotective, anti-inflammatory, and anticancer activities, while some flavonoids exhibit potential antiviral activities. In plant systems, flavonoids help in combating oxidative stress and act as growth regulators. For pharmaceutical purposes cost-effective bulk production of different types of flavonoids has been made possible with the help of microbial biotechnology. This review highlights the structural features of flavonoids, their beneficial roles in human health, and significance in plants as well as their microbial production. PMID:24470791

  3. Citrus Flavonoids as Regulators of Lipoprotein Metabolism and Atherosclerosis.

    Science.gov (United States)

    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.

  4. Chemistry and Biological Activities of Flavonoids: An Overview

    Directory of Open Access Journals (Sweden)

    Shashank Kumar

    2013-01-01

    Full Text Available There has been increasing interest in the research on flavonoids from plant sources because of their versatile health benefits reported in various epidemiological studies. Since flavonoids are directly associated with human dietary ingredients and health, there is need to evaluate structure and function relationship. The bioavailability, metabolism, and biological activity of flavonoids depend upon the configuration, total number of hydroxyl groups, and substitution of functional groups about their nuclear structure. Fruits and vegetables are the main dietary sources of flavonoids for humans, along with tea and wine. Most recent researches have focused on the health aspects of flavonoids for humans. Many flavonoids are shown to have antioxidative activity, free radical scavenging capacity, coronary heart disease prevention, hepatoprotective, anti-inflammatory, and anticancer activities, while some flavonoids exhibit potential antiviral activities. In plant systems, flavonoids help in combating oxidative stress and act as growth regulators. For pharmaceutical purposes cost-effective bulk production of different types of flavonoids has been made possible with the help of microbial biotechnology. This review highlights the structural features of flavonoids, their beneficial roles in human health, and significance in plants as well as their microbial production.

  5. Flavonoids from each of the six structural groups reactivate BRM, a possible cofactor for the anticancer effects of flavonoids

    Science.gov (United States)

    Kahali, Bhaskar; Marquez, Stefanie B.; Thompson, Kenneth W.; Yu, Jinlong; Gramling, Sarah J.B.; Lu, Li; Aponick, Aaron; Reisman, David

    2014-01-01

    Flavonoids have been extensively studied and are well documented to have anticancer effects, but it is not entirely known how they impact cellular mechanisms to elicit these effects. In the course of this study, we found that a variety of different flavonoids readily restored Brahma (BRM) in BRM-deficient cancer cell lines. Flavonoids from each of the six different structural groups were effective at inducing BRM expression as well as inhibiting growth in these BRM-deficient cancer cells. By blocking the induction of BRM with shRNA, we found that flavonoid-induced growth inhibition was BRM dependent. We also found that flavonoids can restore BRM functionality by reversing BRM acetylation. In addition, we observed that an array of natural flavonoid-containing products both induced BRM expression as well as deacetylated the BRM protein. We also tested two of the BRM-inducing flavonoids (Rutin and Diosmin) at both a low and a high dose on the development of tumors in an established murine lung cancer model. We found that these flavonoids effectively blocked development of adenomas in the lungs of wild-type mice but not in that of BRMnull mice. These data demonstrate that BRM expression and function are regulated by flavonoids and that functional BRM appears to be a prerequisite for the anticancer effects of flavonoids both in vitro and in vivo. PMID:24876151

  6. Optimization of microwave-assisted extraction of flavonoids from young barley leaves

    Science.gov (United States)

    Gao, Tian; Zhang, Min; Fang, Zhongxiang; Zhong, Qifeng

    2017-01-01

    A central composite design combined with response surface methodology was utilized to optimise microwave-assisted extraction of flavonoids from young barley leaves. The results showed that using water as solvent, the optimum conditions of microwave-assisted extraction were extracted twice at 1.27 W g-1 microwave power and liquid-solid ratio 34.02 ml g-1 for 11.12 min. The maximum extraction yield of flavonoids (rutin equivalents) was 80.78±0.52%. Compared with conventional extraction method, the microwave-assisted extraction was more efficient as the extraction time was only 6.18% of conventional extraction, but the extraction yield of flavonoids was increased by 5.47%. The main flavonoid components from the young barley leaf extract were probably 33.36% of isoorientin-7-O-glueoside and 54.17% of isovitexin-7-O-glucoside, based on the HPLC-MS analysis. The barley leaf extract exhibited strong reducing power as well as the DPPH radical scavenging capacity.

  7. Bulletin of the Chemical Society of Ethiopia - Vol 6, No 2 (1992)

    African Journals Online (AJOL)

    Flavonoids of polygonum senegalense (MEISN) part II: More surface and internal tissue flavonoid aglycones · EMAIL FREE FULL TEXT EMAIL FREE FULL TEXT · DOWNLOAD FULL TEXT DOWNLOAD FULL TEXT. J. Ogweno Midiwo, N.K. Gikonyo, D.O. Wanjau, J.J. Matasi, P.G. Waterman ...

  8. 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.

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

    Science.gov (United States)

    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.

  10. Flavonoids and sesquiterpenes of Croton pedicellatus Kunth

    International Nuclear Information System (INIS)

    Lopes, Elton Luz; Andrade Neto, Manoel; Silveira, Edilberto Rocha; Pessoa, Otilia Deusdenia Loiola; Braz-Filho, Raimundo

    2012-01-01

    The chemical investigation of the ethanolic extract from leaves of Croton pedicellatus yielded the bis-nor-sesquiterpenes blumenol A and blumenol A glucoside, along with the flavonoids: tiliroside, 6 - O-p-coumaroyl-β-galactopyranosyl- kaempferol, 6 - O-p-coumaroyl-β-glucopyranosyl-3 - methoxy- kaempferol, kaempferol, 3-glucopyranosyl-quercetin and alpinumisoflavone, as well as 4-hydroxy-3,5-dimethoxybenzoic acid. The identification of all isolated compounds was performed by spectrometric methods, including HR-ESI-MS, 1D and 2D NMR experiments, and by comparison with previously-described physical and spectral data. (author)

  11. Flavonoides e sesquiterpenos de Croton pedicellatus Kunth

    Directory of Open Access Journals (Sweden)

    Elton Luz Lopes

    2012-01-01

    Full Text Available The chemical investigation of the ethanolic extract from leaves of Croton pedicellatus yielded the bis-nor-sesquiterpenes blumenol A and blumenol A glucoside, along with the flavonoids: tiliroside, 6"-O-p-coumaroyl-β-galactopyranosyl- kaempferol, 6"-O-p-coumaroyl-β-glucopyranosyl-3"-methoxy- kaempferol, kaempferol, 3-glucopyranosyl-quercetin and alpinumisoflavone, as well as 4-hydroxy-3,5-dimethoxybenzoic acid. The identification of all isolated compounds was performed by spectrometric methods, including HR-ESI-MS, 1D and 2D NMR experiments, and by comparison with previously-described physical and spectral data.

  12. Mechanisms of carcinogenesis prevention by flavonoids

    Directory of Open Access Journals (Sweden)

    G. A. Belitsky

    2014-01-01

    Full Text Available The mechanisms of anticancerogenic effects of flavanoids and isocyanates from the plants widely consumed in the midland belt of Russia were reviewed. Data of studies both in vitro and in vivo were analyzed. Special attention was paid to inhibition of targets responsible for carcinogen metabolic activation, carcinogenesis promotion and tumor progression as well as neoangiogenesis. Besides that the antioxidant properties of flavonoids and their effects on cell cycle regulation, apoptosis initiation and cell mobility were considered.

  13. Inverse association of tea and flavonoid intakes with incident myocardial infarction: the Rotterdam Study

    NARCIS (Netherlands)

    J.M. Geleijnse (Marianne); L.J. Launer (Lenore); D.A. van der Kuip (Deirdre); J.C.M. Witteman (Jacqueline); A. Hofman (Albert)

    2002-01-01

    textabstractBACKGROUND: Dietary flavonoids may protect against cardiovascular disease, but evidence is still conflicting. Tea is the major source of flavonoids in Western populations. OBJECTIVE: The association of tea and flavonoid intake with incident myocardial infarction was

  14. Flavonoid intake and cardiovascular disease mortality in a prospective cohort of US adults

    Science.gov (United States)

    Background: Flavonoids are plant-based phytochemicals with cardiovascular protective properties. Few studies have comprehensively examined flavonoid classes in relation to cardiovascular disease mortality. We examined the association between flavonoid intake and cardiovascular disease (CVD) mortalit...

  15. A comparison of flavonoid glycosides by electrospray tandem mass spectrometry

    Science.gov (United States)

    March, Raymond E.; Lewars, Errol G.; Stadey, Christopher J.; Miao, Xiu-Sheng; Zhao, Xiaoming; Metcalfe, Chris D.

    2006-01-01

    A comparison is presented of product ion mass spectra of protonated and deprotonated molecules of kaempferol-3-O-glucoside, quercitin-3-O-glucoside (isoquercitrin), quercitin-3-O-galactoside (hyperoin), apigenin-7-O-glucoside, luteolin-7-O-glucoside, genistein-7-O-glucoside, naringenin-7-O-glucoside (prunin), luteolin-4'-O-glucoside, luteolin-6-C-glucoside (homoorientin, known also as isoorientin), apigenin-8-C-glucoside (vitexin), and luteolin-8-C-glucoside (orientin) together with the product ion mass spectrum of deprotonated kaempferol-7-O-glucoside. All isomeric ions were distinguishable on the basis of their product ion mass spectra. For protonated 3-O-, 7-O-, and 4'-O-glycosides at a collision energy of 46-47 eV, homolytic cleavage of the O-glycosidic bond yielded aglycon Y+ ions, whereas in deprotonated 3-O-, 7-O-, and 4'-O-glycosides, heterolytic and homolytic cleavage of the O-glycosidic bond yielded radical aglycon (Y-H)- and aglycon (Y-) ions. In each case, fragmentation of either the glycan or the aglycon or both was observed. For 6-C- and 8-C-glycosides at a collision energy of 46-47 eV, fragmentation was restricted almost exclusively to the glycan. For luteolin-6-C-glucoside, the integrity of the aglycon structure is preserved at the expense of the glycan for which some 30 fragmentations were observed. Breakdown curves were determined as a function of collision energy for protonated and deprotonated luteolin-6-C-glucoside. An attempt has been made to rationalize the product ion mass spectra derived from C-O- and C-C-luteolin glucosides in terms of computed structures that indicate significant intramolecular hydrogen bonding and rotation of the B-ring to form a coplanar luteolin structure. It is proposed that protonated and deprotonated luteolin-6-C-glucoside may afford examples of cooperative interactive bonding that plays a major role in directing fragmentation.

  16. Azospirillum brasilense and Azospirillum lipoferum Hydrolyze Conjugates of GA20 and Metabolize the Resultant Aglycones to GA1 in Seedlings of Rice Dwarf Mutants1

    Science.gov (United States)

    Cassán, Fabricio; Bottini, Rubén; Schneider, Gernot; Piccoli, Patricia

    2001-01-01

    Azospirillum species are plant growth-promotive bacteria whose beneficial effects have been postulated to be partially due to production of phytohormones, including gibberellins (GAs). In this work, Azospirillum brasilense strain Cd and Azospirillum lipoferum strain USA 5b promoted sheath elongation growth of two single gene GA-deficient dwarf rice (Oryza sativa) mutants, dy and dx, when the inoculated seedlings were supplied with [17,17-2H2]GA20-glucosyl ester or [17,17- 2H2]GA20-glucosyl ether. Results of capillary gas chromatography-mass spectrometry analysis show that this growth was due primarily to release of the aglycone [17,17-2H2]GA20 and its subsequent 3β-hydroxylation to [17,17-2H2]GA1 by the microorganism for the dy mutant, and by both the rice plant and microorganism for the dx mutant. PMID:11299384

  17. Comparison of the urinary excretion of quercetin glycosides from red onion and aglycone from dietary supplements in healthy subjects: a randomized, single-blinded, cross-over study.

    Science.gov (United States)

    Shi, Yuanlu; Williamson, Gary

    2015-05-01

    Some intervention studies have shown that quercetin supplementation can regulate certain biomarkers, but it is not clear how the doses given relate to dietary quercetin (e.g. from onion). We conducted a two-period, two-sequence crossover study to compare the bioavailability of quercetin when administered in the form of a fresh red onion meal (naturally glycosylated quercetin) or dietary supplement (aglycone quercetin) under fasting conditions. Six healthy, non-smoking, adult males with BMI 22.7 ± 4.0 kg m(-2) and age 35.3 ± 12.3 y were grouped to take the two study meals in random order. In each of the 2 study periods, one serving of onion soup (made from 100 g fresh red onion, providing 156.3 ± 3.4 μmol (47 mg) quercetin) or a single dose of a quercetin dihydrate tablet (1800 ± 150 μmol (544 mg) of quercetin) were administered following 3 d washout. Urine samples were collected up to 24 h, and after enzyme deconjugation, quercetin was quantified by LC-MS. The 24 h urinary excretion of quercetin (1.69 ± 0.79 μmol) from red onion in soup was not significantly different to that (1.17 ± 0.44 μmol) for the quercetin supplement tablet (P = 0.065, paired t-test). This means that, in practice, 166 mg of quercetin supplement would be comparable to about 10 mg of quercetin aglycone equivalents from onion. These data allow intervention studies on quercetin giving either food or supplements to be more effectively compared.

  18. A review on the dietary flavonoid kaempferol.

    Science.gov (United States)

    Calderón-Montaño, J M; Burgos-Morón, E; Pérez-Guerrero, C; López-Lázaro, M

    2011-04-01

    Epidemiological studies have revealed that a diet rich in plant-derived foods has a protective effect on human health. Identifying bioactive dietary constituents is an active area of scientific investigation that may lead to new drug discovery. Kaempferol (3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid found in many edible plants (e.g. tea, broccoli, cabbage, kale, beans, endive, leek, tomato, strawberries and grapes) and in plants or botanical products commonly used in traditional medicine (e.g. Ginkgo biloba, Tilia spp, Equisetum spp, Moringa oleifera, Sophora japonica and propolis). Some epidemiological studies have found a positive association between the consumption of foods containing kaempferol and a reduced risk of developing several disorders such as cancer and cardiovascular diseases. Numerous preclinical studies have shown that kaempferol and some glycosides of kaempferol have a wide range of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, cardioprotective, neuroprotective, antidiabetic, anti-osteoporotic, estrogenic/antiestrogenic, anxiolytic, analgesic and antiallergic activities. In this article, the distribution of kaempferol in the plant kingdom and its pharmacological properties are reviewed. The pharmacokinetics (e.g. oral bioavailability, metabolism, plasma levels) and safety of kaempferol are also analyzed. This information may help understand the health benefits of kaempferol-containing plants and may contribute to develop this flavonoid as a possible agent for the prevention and treatment of some diseases.

  19. DNA Methylation and Flavonoids in Genitourinary Cancers.

    Science.gov (United States)

    Mukherjee, Neelam; Kumar, Addanki P; Ghosh, Rita

    2015-04-01

    Malignancies of the genitourinary system have some of the highest cancer incidence and mortality rates. For example prostate cancer is the second most common cancer in men and ovarian cancer mortality and incidence are near equal. In addition to genetic changes modulation of the epigenome is critical to cancer development and progression. In this regard epigenetic changes in DNA methylation state and DNA hypermethylation in particular has garnered a great deal of attention. While hypomethylation occurs mostly in repeated sequence such as tandem and interspersed repeats and segment duplications, hypermethylation is associated with CpG islands. Hypomethylation leads to activation of cancer-causing genes with global DNA hypomethylation being commonly associated with metastatic disease. Hypermethylation-mediated silencing of tumor suppressive genes is commonly associated with cancer development. Bioactive phytochemicals such as flavonoids present in fruits, vegetables, beverages etc. have the ability to modulate DNA methylation status and are therefore very valuable agents for cancer prevention. In this review we discuss several commonly methylated genes and flavonoids used to modulate DNA methylation in the prevention of genitourinary cancers.

  20. FLAVONOID NATURAL SOURCES AND THEIR IMPORTANCE IN THE HUMAN DIET

    Directory of Open Access Journals (Sweden)

    Martina Danihelová

    2011-12-01

    Full Text Available Flavonoids as natural bioactive compounds are present in almost every sort of fruits, vegetables and from them derived products. Flavonols may be found mainly in fruits and vegetables, while flavones are abundant in herbs and spices. Rich natural sources of flavanols are tea, cocoa, grape seeds or apple skin. Flavanones are primarily found in a variety of citrus fruits and anthocyanidins in many coloured berries. Soy is rich in isoflavonoids. Average daily intake of flavonoids is approximately in the range of 150 to 300 mg. It strongly depends on individual, country and culture usages. In west countries main dietary sources of flavonoids consist of tea, wine and fruits, while in east countries there is consumed mainly soy with high isoflavonoid content. Many studies have shown, that intake of fruits and vegetables with high flavonoid content is associated with lowered risk of incidence of some diseases such as cardiovascular or cancer. These findings are attributed to experimentally confirmed biological effects of flavonoids - antioxidant, anti-inflammatory, anti-allergic, anticancer or cardioprotective. The final effect is however depending on their bioavailability, which is in the case of flavonoids not high, because in the nature dominating flavonoid glycosides can poorly penetrate through lipophilic cell membranes. Final effective molecules are flavonoid metabolites, that more or less retain their biological activities. doi: 10.5219/160

  1. Antimicrobial potential of alkaloids and flavonoids extracted from ...

    African Journals Online (AJOL)

    Background: Alkaloids and flavonoids are secondary metabolites extracted from different medicinal plants. Tamarix aphylla a traditionally valuable medicinal plant; was used for the extraction of alkaloids and flavonoids in order to evaluate their antibacterial activity. Methodology: The leaves of the plant were collected from ...

  2. flavonoid constituents of the mature fruit of tetrapleura tetraptera

    African Journals Online (AJOL)

    Prince Acheampong

    report of the isolation of such consti-tuents from the genus Tetrapleura, although as a class of secondary metabolites, flavonoids have been reported to occur in some parts of T. tetraptera including the stem bark. (El-izzi et al., 1990). Secondly, the isolated flavonoids have demonstrated various biological activities. For.

  3. Beneficial Effect of the Flavonoid Luteolin on Neuroinflammation

    Science.gov (United States)

    Jang, Saebyeol

    2009-01-01

    Excessive production of pro-inflammatory mediators by activated brain microglia plays an important role in abnormal neuronal function and cognitive deficits. Studies have shown that the intake of flavonoids is inversely related to cognitive decline and dementia in people 65 years of age or older. Luteolin, a flavonoid found in high concentrations…

  4. Comparative yield and characterization of flavonoids from the stem ...

    African Journals Online (AJOL)

    Flavonoids represent a wide spread group of water soluble phenolic derivatives, known for their medicinal effect. This paper is focused on identifying the functional groups present in flavonoids of Blighia sapida stem bark and root sample. The percentage yield was higher with methanol extract of the stem bark compared to ...

  5. Isolation of flavonoids from mulberry ( Morus alba L.) leaves with ...

    African Journals Online (AJOL)

    Flavonoids are major active constituents in mulberry (Morus alba L.) leaves and possess various pharmacological activities. In the present study, the extraction technology and preparative separation of total flavonoids (TFs) in mulberry leaves extracts by macroporous resins were studied systematically, and the column ...

  6. Cytoprotective effects of dietary flavonoids against cadmium-induced toxicity.

    Science.gov (United States)

    Li, Xia; Jiang, Xinwei; Sun, Jianxia; Zhu, Cuijuan; Li, Xiaoling; Tian, Lingmin; Liu, Liu; Bai, Weibin

    2017-06-01

    Cadmium (Cd) damages the liver, kidney, bones, reproductive system, and other organs. Flavonoids, such as anthocyanins and flavonols, which are commonly found in plant foods, have shown protective effects against Cd-induced damage. The cytoprotective effects of flavonoids against Cd-induced diseases are mainly attributable to three mechanisms. First, flavonoids clear reactive oxygen species, thereby reducing lipid peroxide production and improving the activity of antioxidation enzymes. Second, flavonoids chelate Cd, thus reducing the accumulation of Cd and altering the levels of other essential metal ions in vivo. Third, flavonoids reduce DNA damage and inhibit apoptosis. In addition, flavonoids were found to inhibit inflammation and fibrosis and improve glycometabolism and the secretion of reproductive hormones. We introduce the daily dosage and absorption rate of flavonoids and then focus on their bioactive effects against Cd-induced toxicity and reveal the underlying metabolic pathway, which provides a basis for further study of the nutritional prevention of Cd-induced injury. In particular, a better understanding is needed of the structure-activity relationship of flavonoids against Cd toxicity, which has not yet been reported. © 2017 New York Academy of Sciences.

  7. Antibacterial, anti-inflammatory and diuretic effect of flavonoids from ...

    African Journals Online (AJOL)

    Dried leaves of Marchantia convoluta are largely used to protect livers, and to treat tumefaction of skins in China. Flavonoids from Marchantia convoluta (MCF) were the active components against hepatitis B virus. In this study, the pharmacological properties of MCF consisting of flavonoids determined by HPLC were ...

  8. Dietary supplementation with mulberry leaf flavonoids inhibits methanogenesis in sheep.

    Science.gov (United States)

    Ma, Tao; Chen, Dan-Dan; Tu, Yan; Zhang, Nai-Feng; Si, Bing-Wen; Diao, Qi-Yu

    2017-01-01

    The effects of flavonoids on methanogenesis and microbial flora in Dorper × thin-tailed Han crossbred ewes were evaluated in two experiments. To investigate the effects of flavonoids on nutrient digestibility and nitrogen balance, 18 ewes (60.0 ± 1.73 kg body weight (BW)) were allotted to two dietary treatments in experiment one, a control diet and the control diet supplemented with flavonoids (2 g/head/day). In experiment two, the effects of supplementary flavonoids on ruminal fermentation and microbial flora were investigated using quantitative polymerase chain reaction with six ewes (67.2 ± 0.79 kg BW) with ruminal cannula assigned to the identical dietary treatments used in experiment one. Supplementary flavonoids improved the apparent digestibility of nitrogen (N, P flavonoids, whereas the total volatile fatty acid (VFA) content increased (P = 0.037). Supplementary flavonoids decreased ruminal populations of protozoans (P = 0.002) and methanogens (P flavonoids improved the digestibility of organic matter and reduced CH 4 output by inhibiting the populations of microbes involved in methanogenesis. © 2016 Japanese Society of Animal Science.

  9. Evaluation of Anti-Fatigue Activity of Flavonoids from Tartary ...

    African Journals Online (AJOL)

    Background: Flavonoids are the major biological activities components of tartary buckwheat which has multifunctional bioactivities. However, there are a limited number of studies on the effect of flavonoids from tartary buckwheat (TBF) on physical fatigue at present. This study aimed to investigate the anti-fatigue activity of ...

  10. Quantification of Tea Flavonoids by High Performance Liquid Chromatography

    Science.gov (United States)

    Freeman, Jessica D.; Niemeyer, Emily D.

    2008-01-01

    We have developed a laboratory experiment that uses high performance liquid chromatography (HPLC) to quantify flavonoid levels in a variety of commercial teas. Specifically, this experiment analyzes a group of flavonoids known as catechins, plant-derived polyphenolic compounds commonly found in many foods and beverages, including green and black…

  11. Cytotoxic flavonoids from Erythrina caffra Thunb | Y. Desta | Bulletin ...

    African Journals Online (AJOL)

    Erythrina caffra is an important medicinal plant native to South Africa. Its stem bark was investigated for the flavonoid constituents and biological activity. Some isolated flavonoids, 3, 5, 6, 8, 9, 10, 11, 12, 13, 15 and 16 were found to be active against the human cervix carcinoma KB-3-1 cells with IC50 values in the ...

  12. Consumer attitudes towards enhanced flavonoid content in fruit

    NARCIS (Netherlands)

    Lampila, P.; Lieshout, van M.; Gremmen, H.G.J.; Lahteenmaki, L.

    2009-01-01

    Flavonoids from fruit and vegetables are currently widely studied as components that have the potential to provide multiple health benefits. In this study consumer perceptions of flavonoids were examined. The data (N = 130) were collected in focus group discussions in Finland, The Netherlands and

  13. Efficacy of Food Proteins as Carriers for Flavonoids

    NARCIS (Netherlands)

    Bohin, M.C.; Vincken, J.P.; Hijden, H.T.W.M.; Gruppen, H.

    2012-01-01

    Enrichment of flavonoids in food is often limited by their off-tastes, which might be counteracted by the use of food proteins as carriers of flavonoids. Various milk proteins, egg proteins, and gelatin hydrolysates were compared for their binding characteristics to two flavan-3-ols. Among the

  14. Extraction and Purification of Flavonoids from Radix Puerariae

    African Journals Online (AJOL)

    content of puerarin and flavonoids in the samples were tested by a HPLC and a UV-Vis. Spectrophotometer, respectively. ... the weight of the crude drug), the volume of loading sample is 2 BV (bed volume). The mobile phases of desorption are ... flavonoids, they have a variety of biological activities [1-3] including improving ...

  15. Tyrosinase Inhibitory Activity and Thermostability of the Flavonoid ...

    African Journals Online (AJOL)

    Purpose: To investigate the tyrosinase inhibitory activity and thermostability of weak acid-treated Sophora japonica L. flavonoid complex (SJ-FC) in different solutions. Methods: The flavonoid complex of S. japonica was isolated and treated with weak acid to generate SJ-FC. The anti-tyrosinase activities of SJ-FC and ...

  16. Brosimacutins A-I, nine new flavonoids from Brosimum acutifolium.

    Science.gov (United States)

    Takashima, Junko; Ohsaki, Ayumi

    2002-12-01

    Nine new flavonoids, brosimacutins A-I (1-9), and four known flavonoids were isolated from the bark of Brosimum acutifolium, a Brazilian folk medicine ("Mururé"). Their structures were elucidated by spectroscopic methods, including 2D NMR. Brosimacutins A-I possess differentially functionalized isoprene units at C-8.

  17. Flavonoids patterns of French honeys with different floral origin

    NARCIS (Netherlands)

    Soler, C.; Gil, M.I.; Garcia-Viguera, C.; Tomás-Barberán, F.A.

    1995-01-01

    The flavonoid profiles of 12 different unifloral French honey samples were analysed by HPLC to evaluate if these substances could be used as markers of the floral origin of honey. In this analysis, the characteristic flavonoids from propolis and/or beeswax (chrysin, galangin, tectochrysin,

  18. Antimicrobial action of purified raspberry flavonoid | Sun | African ...

    African Journals Online (AJOL)

    ... flavonoid on Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Saccharomyces cerevisiae, Rhizopus, Mucor and Penicillium. Raspberry flavonoid had the best inhibition effect on S. aureus, followed by B. subtilis, E. coli and Penicillium. However, it cannot inhibit the growth of S. cerevisiae, Rhizopus and Mucor.

  19. Flavonoids in the development of functional meat products: A review

    Directory of Open Access Journals (Sweden)

    Pramod K. Singh

    2013-06-01

    Full Text Available Flavonoids or bioflavonoids are unique low molecular weight ubiquitous polyphenolic compounds produced by plants during their metabolic activities as a secondary metabolites and responsible for major organoleptic characteristics and health benefits of plant derived foods. The flavonoids are potent antioxidants agents and protect the cells by scavenging and inhibiting the production and initiation of free radicals, superoxide anions and lipid peroxy radicals. Besides potent antioxidant capacity, flavonoids also shows antimicrobial, antimutagenic, antidiabetic, antithrombosis, antirheumatic, antiatherosclerotic, antiallergic, anti-inflammatory, antiulcers and hepatoprotectives and better termed as neutraceuticals. The antioxidant capacity of meat is very low and this can be increased by adding flavonoids in meat during processing in the form of plant parts rich in flavonoids such as seeds, fruit skin or peel, bark and flower as raw or in extract form without comprising the sensory attributes of meat and meat products. [Vet World 2013; 6(8.000: 573-578

  20. The therapeutic potential of plant flavonoids on rheumatoid arthritis.

    Science.gov (United States)

    Hughes, Samuel D; Ketheesan, Natkunam; Haleagrahara, Nagaraja

    2017-11-22

    Rheumatoid arthritis (RA) is an autoimmune condition that mainly affects peripheral joints. Although immunosuppressive drugs and non-steroidal anti-inflammatory drugs (NSAIDs) are used to treat this condition, these drugs have severe side effects. Flavonoids are the most abundant phenolic compounds which exhibit anti-oxidant, anti-inflammatory and immunomodulatory properties. Many bioactive flavonoids have powerful anti-inflammatory effects. However, a very few have reached clinical use. Dietary flavonoids have been reported to control joint inflammation and alleviate arthritis symptoms in both human RA and animal models of arthritis. There is little scientific evidence about their mechanism of actions in RA. We review the therapeutic effects of different groups of flavonoids belonging to the most common and abundant groups on RA. In particular, the probable mechanisms of major flavonoids on cells and chemical messengers involved in the inflammatory signaling components of RA are discussed in detail.

  1. Floral flavonoids and ultraviolet patterns in Viguiera (Compositae)

    International Nuclear Information System (INIS)

    Rieseberg, L.H.; Schilling, E.E.

    1985-01-01

    Variation occurs among species of Viguiera series Viguiera for ultraviolet (UV) absorption/reflection patterns of ligules. Floral flavonoids that cause UV absorption occur in epidermal papillae. Flavonoids are further localized to the proximal portion of the ligule in the seven taxa that have only proximal UV absorption. Floral flavonoids involved in UV absorption consist of flavone, flavonol, and anthochlor (chalcone/aurone) glycosides. Quercetin 3-methyl ether glycosides characterize the ligules of 10 taxa occurring in Baja California, Mexico, and nearby areas, and these taxa appear to form one taxonomic group. The anthochlor pair, marein/maritimein, characterizes V. dentata, and the lack of ligule flavonoids distinguishes V. potosina from the remaining taxa. The presence of the anthochlor pair, marein/maritimein, only in V. dentata and the lack of ligule flavonoids in V. potosina concur with other data to indicate that these species are not correctly placed with each other or with the other species currently included in series Viguiera. (author)

  2. The flavonoid biosynthetic pathway in plants: function and evolution

    International Nuclear Information System (INIS)

    Koes, R.E.; Quattrocchio, F.; Mol, J.N.M.

    1994-01-01

    Flavonoids are a class of low molecular weight phenolic compounds that is widely distributed in the plant kingdom. They exhibit a diverse spectrum of biological functions and play an important role in the interaction between plants and their environment. Flavonoids not only protect the plant from the harmful effects of UV irradiation but also play a crucial role in the sexual reproduction process. A special class of flavonoid polymers, the tannins, plays a structural role in the plant. Yet other classes of flavonoids, flavonols and anthocyanins, have been implicated in the attraction of pollinators. Certain flavonoids participate in the interaction between plants and other organisms such as symbiotic bacteria and parasites. This raises the intriguing question as to how these different compounds arose and evolved. Based on taxonomy and molecular analysis of gene expression patterns it is possible to deduce a putative sequence of acquisition of the different branches of the biosynthetic pathway and their regulators. (author)

  3. Cranberry Flavonoids Modulate Cariogenic Properties of Mixed-Species Biofilm through Exopolysaccharides-Matrix Disruption.

    Directory of Open Access Journals (Sweden)

    Dongyeop Kim

    Full Text Available The exopolysaccharides (EPS produced by Streptococcus mutans-derived glucosyltransferases (Gtfs are essential virulence factors associated with the initiation of cariogenic biofilms. EPS forms the core of the biofilm matrix-scaffold, providing mechanical stability while facilitating the creation of localized acidic microenvironments. Cranberry flavonoids, such as A-type proanthocyanidins (PACs and myricetin, have been shown to inhibit the activity of Gtfs and EPS-mediated bacterial adhesion without killing the organisms. Here, we investigated whether a combination of cranberry flavonoids disrupts EPS accumulation and S. mutans survival using a mixed-species biofilm model under cariogenic conditions. We also assessed the impact of cranberry flavonoids on mechanical stability and the in situ pH at the biofilm-apatite interface. Topical application of an optimized combination of PACs oligomers (100-300 μM with myricetin (2 mM twice daily was used to simulate treatment regimen experienced clinically. Treatments with cranberry flavonoids effectively reduced the insoluble EPS content (>80% reduction vs. vehicle-control; p<0.001, while hindering S. mutans outgrowth within mixed-species biofilms. As a result, the 3D architecture of cranberry-treated biofilms was severely compromised, showing a defective EPS-matrix and failure to develop microcolonies on the saliva-coated hydroxyapatite (sHA surface. Furthermore, topical applications of cranberry flavonoids significantly weaken the mechanical stability of the biofilms; nearly 90% of the biofilm was removed from sHA surface after exposure to a shear stress of 0.449 N/m2 (vs. 36% removal in vehicle-treated biofilms. Importantly, in situ pH measurements in cranberry-treated biofilms showed significantly higher pH values (5.2 ± 0.1 at the biofilm-apatite interface vs. vehicle-treated biofilms (4.6 ± 0.1. Altogether, the data provide important insights on how cranberry flavonoids treatments modulate

  4. Prenylated flavonoids from maclura tinctoria fruits

    International Nuclear Information System (INIS)

    Oyama, Sayuri de Oliveira; Souza, Luiz Antonio de; Baldoqui, Debora Cristina; Sarragiotto, Maria Helena; Silva, Adriano Antônio

    2013-01-01

    A phytochemical investigation of Maclura tinctoria fruits yielded five flavonoids, including one prenylated flavonol (licoflavonol) and four prenylated isoflavones (wighteone, derrone, alpinum isoflavone, and 6-(2,2-dimethyl-2H-chromen-6-yl)-2-(1-hydroxy-1-methylethyl) -2,3-dihydro-5H-furo[3,2-g]chromen-5-one). The structures of the isolates were established by analyzing their spectroscopic data. Compound 6-(2,2-dimethyl-2H-chromen-6-yl) -2-(1-hydroxy-1-methylethyl)-2,3-ihydro-5H-furo[3,2-g]chromen-5-one is new and the other isolates are described for the first time in this species. (author)

  5. Prenylated flavonoids from maclura tinctoria fruits

    Directory of Open Access Journals (Sweden)

    Sayuri de Oliveira Oyama

    2013-01-01

    Full Text Available A phytochemical investigation of Maclura tinctoria fruits yielded five flavonoids, including one prenylated flavonol (licoflavonol and four prenylated isoflavones (wighteone, derrone, alpinum isoflavone, and 6-(2,2-dimethyl-2H-chromen-6-yl-2-(1-hydroxy-1-methylethyl-2,3-dihydro-5H-furo[3,2-g]chromen-5-one. The structures of the isolates were established by analyzing their spectroscopic data. Compound 6-(2,2-dimethyl-2H-chromen-6-yl-2-(1-hydroxy-1-methylethyl-2,3-dihydro-5H-furo[3,2-g]chromen-5-one is new and the other isolates are described for the first time in this species.

  6. Flavonoids from Twigs of Millettia leptobotrya Dunn.

    Directory of Open Access Journals (Sweden)

    Zhi Na

    2013-08-01

    Full Text Available A new furanoisoflavone, 2 ' -methoxy-4 ' ,5 ' -methylenedioxy-[2 '' ,3 '' :7,8 ] furanoisoflavone, leptobotryanone ( 1 , and a new natural O-prenylated isoflavone, 4 ' -γ,γ-dimethylallyloxy-5,7-dihydroxyisoflavone ( 2 , were isolated from the twig s of Millettia leptobotrya, together with twelve known flavonoids, 4 ' -γ,γ-dimethylallyloxy-5-hydroxy-7-methoxyisoflavone ( 3 , 2 ' ,6,7-trimethoxy-4 ' ,5 ' -methylenedioxy- isoflavone (4, 2 ' ,7-dimethoxy-4 ' ,5 ' -methylenedioxyisoflavone (5, maximaisoflavone B (6, medicarpin (7 , maackiain (8, genistein (9, biochanin A (10, prunetin (11, chrysoeriol (12 , kaempferol (13 and desmoxyphyllin A (14 The structures of new compounds were elucidated on the basis of spectroscopic data interpretation , including 1D and 2D NMR and HREIMS. Th is is the first phytochemical investigation of this plant.

  7. Prenylated flavonoids from Commiphora opobalsamum stem bark.

    Science.gov (United States)

    El-Gamal, Ali A; Al-Massarani, Shaza M; Abdel-Mageed, Wael M; El-Shaibany, Amina; Al-Mahbashi, Hassan M; Basudan, Omer A; Badria, Farid A; Al-Said, Mansour S; Abdel-Kader, Maged S

    2017-09-01

    A phytochemical study on the stem bark of Commiphora opobalsamum looking for cytotoxic compounds afforded eleven flavonoids, including six previously undescribed prenylated congeners, comophorin A-E, and comophoroside A. The structures of the isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Isolated compounds were biologically evaluated using in vitro cytotoxicity MTT-based assay against two cancer cell lines; namely human hepato-cellular carcinoma (HepG-2) and human breast adenocarcinoma (MCF-7). Comophoroside A revealed to retain the strongest cytotoxic activity against MCF-7 and HepG-2 cell lines with IC 50 values of 8 and 12 μg/mL, respectively. Copyright © 2017 Elsevier Ltd. All rights reserved.

  8. Prenylated flavonoids from maclura tinctoria fruits

    Energy Technology Data Exchange (ETDEWEB)

    Oyama, Sayuri de Oliveira; Souza, Luiz Antonio de [Departamento de Biologia, Universidade Estadual de Maringa, PR (Brazil); Baldoqui, Debora Cristina; Sarragiotto, Maria Helena [Departamento de Quimica, Universidade Estadual de Maringa, PR (Brazil); Silva, Adriano Antonio, E-mail: aasilva@ufac.br [Departamento de Ciencias da Natureza, Universidade Federal do Acre, AC (Brazil)

    2013-09-01

    A phytochemical investigation of Maclura tinctoria fruits yielded five flavonoids, including one prenylated flavonol (licoflavonol) and four prenylated isoflavones (wighteone, derrone, alpinum isoflavone, and 6-(2,2-dimethyl-2H-chromen-6-yl)-2-(1-hydroxy-1-methylethyl) -2,3-dihydro-5H-furo[3,2-g]chromen-5-one). The structures of the isolates were established by analyzing their spectroscopic data. Compound 6-(2,2-dimethyl-2H-chromen-6-yl) -2-(1-hydroxy-1-methylethyl)-2,3-ihydro-5H-furo[3,2-g]chromen-5-one is new and the other isolates are described for the first time in this species. (author)

  9. Plant Flavonoid Content Modified by Domestication.

    Science.gov (United States)

    Chacón-Fuentes, Manuel; Parra, Leonardo; Lizama, Marcelo; Seguel, Ivette; Urzúa, Alejandro; Quiroz, Andrés

    2017-10-01

    Plant domestication can modify and weaken defensive chemical traits, reducing chemical defenses in plants and consequently their resistance against pests. We characterized and quantified the major defensive flavonols and isoflavonoids present in both wild and cultivated murtilla plants (Ugni molinae Turcz), established in a common garden. We examined their effects on the larvae of Chilesia rudis (Butler) (Lepidoptera: Arctiidae). Insect community and diversity indices were also evaluated. We hypothesized that domestication reduces flavonoid contents and modifies C. rudis preference, the insect community, and diversity. Methanolic extracts were obtained from leaves of U. molinae plants and analyzed by high performance liquid chromatography. Results showed higher insect numbers (86.48%) and damage index (1.72 ± 0.16) in cultivated plants. Four new first records of insects were found associated with U. molinae. Diversity indices, such as Simpson, Shannon, and Margalef, were higher in cultivated plants than in wild plants. Furthermore, eight isoflavonoids were identified in U. molinae leaves for the first time. The five flavonols showed higher concentrations in wild U. molinae leaves (89.8 µg/g) than in cultivated plants (75.2 µg/g); however, no differences were found in isoflavonoids between wild and cultivated plants. The larvae of C. rudis consumed more leaf material of cultivated plants than wild plants in choice (3.8 vs. 0.8 mm2) and no-choice (7.5 vs. 3.0 mm2) assays. Our study demonstrates that domestication in U. molinae reduces the amount of flavonoids in leaves, increasing the preference of C. rudis and the insect community. © The Authors 2017. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

  10. [Extraction and purification technologies of total flavonoids from Aconitum tanguticum].

    Science.gov (United States)

    Li, Yan-Rong; Yan, Li-Xin; Feng, Wei-Hong; Li, Chun; Wang, Zhi-Min

    2014-04-01

    To optimize the extraction and purification technologies of total flavonoids from Aconitum tanguticum whole plant. With the content of total flavonoids as index, the optimum extraction conditions for the concentration, volume of alcohol, extracting time and times were selected by orthogonal optimized; Comparing the adsorption quantity (mg/g) and resolution (%), four kinds of macroporous adsorption resins including D101, AB-8, X-5 and XAD-16 were investigated for the enrichment ability of total flavonoids from Aconitum tanguticum; Concentration and pH value of sample, sampling amount, elution solvent and loading and elution velocity for the optimum adsorption resin were determined. The content of total flavonoids in Aconitum tanguticum was about 4.39%; The optimum extraction technique was 70% alcohol reflux extraction for three times,each time for one hour, the ratio of material and liquid was 1:10 (w/v); The optimum purification technology was: using XAD-16 macroporous resin, the initial concentration of total flavonoids of Aconitum tanguticum was 8 mg/mL, the sampling amount was 112 mg/g dry resin, the pH value was 5, the loading velocity was 3 mL/min, the elution solvent was 70% ethanol and the elution velocity was 5 mL/min. Under the optimum conditions, the average content of total flavonoids was raised from 4.39% to 46.19%. The optimum extraction and purification technologies for total flavonoids of Aconitum tanguticum were suitable for industrial production for its simplicity and responsibility.

  11. A kinetic model for flavonoid production in tea cell culture.

    Science.gov (United States)

    Shibasaki-Kitakawa, Naomi; Iizuka, Yasuhiro; Takahashi, Atsushi; Yonemoto, Toshikuni

    2017-02-01

    As one of the strategies for efficient production of a metabolite from cell cultures, a kinetic model is very useful tool to predict productivity under various culture conditions. In this study, we propose a kinetic model for flavonoid production in tea cell culture based on the cell life cycle and expression of PAL, the gene encoding phenylalanine ammonia-lyase (PAL)-the key enzyme in flavonoid biosynthesis. The flavonoid production rate was considered to be related to the amount of active PAL. Synthesis of PAL was modelled based on a general gene expression/translation mechanism, including the transcription of DNA encoding PAL into mRNA and the translation of PAL mRNA into the PAL protein. The transcription of DNA was assumed to be promoted at high light intensity and suppressed by a feedback regulatory mechanism at high flavonoid concentrations. In the model, mRNA and PAL were considered to self-decompose and to be lost by cell rupture. The model constants were estimated by fitting the experimental results obtained from tea cell cultures under various light intensities. The model accurately described the kinetic behaviors of dry and fresh cell concentrations, glucose concentration, cell viability, PAL specific activity, and flavonoid content under a wide range of light intensities. The model simulated flavonoid productivity per medium under various culture conditions. Therefore, this model will be useful to predict optimum culture conditions for maximum flavonoid productivity in cultured tea cells.

  12. Flavonoids as modulators of metabolic enzymes and drug transporters.

    Science.gov (United States)

    Miron, Anca; Aprotosoaie, Ana Clara; Trifan, Adriana; Xiao, Jianbo

    2017-06-01

    Flavonoids, natural compounds found in plants and in plant-derived foods and beverages, have been extensively studied with regard to their capacity to modulate metabolic enzymes and drug transporters. In vitro, flavonoids predominantly inhibit the major phase I drug-metabolizing enzyme CYP450 3A4 and the enzymes responsible for the bioactivation of procarcinogens (CYP1 enzymes) and upregulate the enzymes involved in carcinogen detoxification (UDP-glucuronosyltransferases, glutathione S-transferases (GSTs)). Flavonoids have been reported to inhibit ATP-binding cassette (ABC) transporters (multidrug resistance (MDR)-associated proteins, breast cancer-resistance protein) that contribute to the development of MDR. P-glycoprotein, an ABC transporter that limits drug bioavailability and also induces MDR, was differently modulated by flavonoids. Flavonoids and their phase II metabolites (sulfates, glucuronides) inhibit organic anion transporters involved in the tubular uptake of nephrotoxic compounds. In vivo studies have partially confirmed in vitro findings, suggesting that the mechanisms underlying the modulatory effects of flavonoids are complex and difficult to predict in vivo. Data summarized in this review strongly support the view that flavonoids are promising candidates for the enhancement of oral drug bioavailability, chemoprevention, and reversal of MDR. © 2017 New York Academy of Sciences.

  13. Flavonoid intake in European adults (18 to 64 years.

    Directory of Open Access Journals (Sweden)

    Anna Vogiatzoglou

    Full Text Available Flavonoids are a group of phenolic secondary plant metabolites that are ubiquitous in plant-based diets. Data from anthropological, observational and intervention studies have shown that many flavonoids are bioactive. For this reason, there is an increasing interest in investigating the potential health effects of these compounds. The translation of these findings into the context of the health of the general public requires detailed information on habitual dietary intake. However, only limited data are currently available for European populations.The objective of this study is to determine the habitual intake and main sources of anthocyanidins, flavanols, flavanones, flavones, flavonols, proanthocyanidins, theaflavins and thearubigins in the European Union.We use food consumption data from the European Food Safety Authority (EFSA and the FLAVIOLA Food Composition Database to estimate intake of flavonoids.Mean (±SEM intake of total flavonoids in Europe was 428±49 mg/d, of which 136±14 mg/d were monomeric compounds. Gallated flavan-3-ols (53±12 mg/d were the main contributor. The lowest flavonoid intake was observed in Mediterranean countries (monomeric compounds: 95±11 mg/d. The distribution of intake was skewed in many countries, especially in Germany (monomeric flavonoids; mean intake: 181 mg/d; median intake: 3 mg/d.The habitual intake of flavonoids in Europe is below the amounts found to have a significant health effect.

  14. Flavonoids as Important Molecules of Plant Interactions with the Environment

    Directory of Open Access Journals (Sweden)

    Justyna Mierziak

    2014-10-01

    Full Text Available Flavonoids are small molecular secondary metabolites synthesized by plants with various biological activities. Due to their physical and biochemical properties, they are capable of participating in plants’ interactions with other organisms (microorganisms, animals and other plants and their reactions to environmental stresses. The majority of their functions result from their strong antioxidative properties. Although an increasing number of studies focus on the application of flavonoids in medicine or the food industry, their relevance for the plants themselves also deserves extensive investigations. This review summarizes the current knowledge on the functions of flavonoids in the physiology of plants and their relations with the environment.

  15. Spray Drying of Rhodomyrtus tomentosa (Ait. Hassk. Flavonoids Extract: Optimization and Physicochemical, Morphological, and Antioxidant Properties

    Directory of Open Access Journals (Sweden)

    Pingping Wu

    2014-01-01

    Full Text Available The optimal condition of spray drying purified flavonoids extract from R. tomentosa berries was studied by response surface methodology. The optimized condition for microencapsulation was of maltodextrin to gum Arabic ratio 1 : 1.3, total solid content 27.4%, glycerol monostearate content 0.25%, and core to coating material ratio 3 : 7, resulting in EE 91.75%. Prepared at the optimized condition, the flavonoids extract microcapsules (FEMs were irregularly spherical particles with low moisture content (3.27%, high solubility (92.35%, and high bulk density (0.346 g/cm3. DPPH radical scavenging activity of FEMs was not decreased after spray drying (P>0.05 and higher than those in citric acid and rutin at the same concentration. Moreover, FEMs effectively retarded the oxidation of fresh lard during the 10-day storage period compared with vitamin C, nonencapsulated flavonoids extract, and rutin. Therefore, FEMs produced at the optimized condition could be used as powder ingredients with antioxidant capacities.

  16. Flavonoids in baby spinach (Spinacia oleracea L.): Changes during plant growth and storage

    DEFF Research Database (Denmark)

    Bergquist, S. Å. M.; Gertsson, U. E.; Knuthsen, Pia

    2005-01-01

    The variation in flavonoid concentration and composition was investigated in baby spinach (Spinacia oleracea L.) cv. Emilia sown on three occasions, each harvested at three growth stages at 6-day intervals. After harvest, leaves were stored in polypropylene bags at 2 or 10 degrees C. Flavonoids...... were analyzed by reversed phase HPLC. Twelve flavonoid peaks were detected. The main flavonoid, making up on average 43% of the total flavonoid concentration, was identified as 5,3',4'-trihydroxy-3-methoxy-6:7-methylenedioxyflavone-4'-glucuronide. Four other flavonoids each contributed 7......-12% of the total flavonoid content. Total flavonoid content was relatively stable during normal retail storage conditions, although some of the individual flavonoid compounds showed considerable variation. The youngest plants had the highest flavonoid concentration, indicating that by harvesting the baby spinach...

  17. Flavonoids and antioxidant activity of flowers of Mexican Crataegus spp.

    Science.gov (United States)

    García-Mateos, Rosario; Aguilar-Santelises, Leonor; Soto-Hernández, Marcos; Nieto-Angel, Raúl

    2013-01-01

    Flavonoids and antioxidant activity of extracts of flowers from some Mexican accessions of Crataegus were studied using six accessions with the purpose of contributing to the knowledge of the nutraceutical properties of the accessions of the Germplasm Bank of the Universidad Autonoma Chapingo. Flavonoids were identified by HPLC-MS. Among the flavonoids, the quercetin 3-O-glucoside (3), quercetin 3-O-rhamnoside (4), quercetin 3-O-rhamnosyl-(1 → 6)-glucoside (2) and quercetin 3-O-rhamnosyl-(1 → 2)-[rhamnosyl-(1 → 6)]-glucoside (1) were assigned. Flavonoid content and radical scavenging activity explain some of the medicinal properties attributed to flowers of Mexican hawthorns.

  18. Flavonoid Functions in Plants and Their Interactions with Other Organisms

    Directory of Open Access Journals (Sweden)

    Ulrike Mathesius

    2018-04-01

    Full Text Available Flavonoids are structurally diverse secondary metabolites in plants, with a multitude of functions. These span from functions in regulating plant development, pigmentation, and UV protection, to an array of roles in defence and signalling between plants and microorganisms. Because of their prevalence in the human diet, many flavonoids constitute important components of medicinal plants and are used in the control of inflammation and cancer prevention. Advances in the elucidation of flavonoid biosynthesis and its regulation have led to an increasing number of studies aimed at engineering the flavonoid pathway for enhancing nutritional value and plant defences against pathogens and herbivores, as well as modifying the feeding value of pastures. Many future opportunities await for the exploitation of this colourful pathway in crops, pastures, and medicinal plants.

  19. 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...

  20. Study the active site of flavonoid applying radiation chemistry

    International Nuclear Information System (INIS)

    Wu Jilan; Sun Gang; Zhang Fugen; He Yongke; Li Jiuqiang

    2000-01-01

    Flavonoid are a large and important class of naturally occurring, low molecular weight benzo-γ-pyrone derivatives which are reported to have a myriad of biological activities, but the study on the active sites of flavonoids is still ambiguous. In this paper, rutin, quercetin and baicalin have been selected as model compounds. It is well known that rutin is used in inhibiting arteriosclerosis and baicalin is antibacterial and antiviral. They have similar basic structure, but their medicinal properties are so different, why? As most flavonoids contain carbonyl group, which can capture electron effectively, we predict that flavonoids can capture electron to form radical anion. The formation of anion radical may have influence on the mitochondrial electron transport chain. The difference in the ability of forming anion radical may cause the difference in their medicinal effects. (author)

  1. Intervention of Prostate Cancer by a Flavonoid Antioxidant Silymarin

    National Research Council Canada - National Science Library

    Agarwal, Rajesh

    1999-01-01

    ...). We rationalized that targeting this pathway would be useful for PCA intervention, and showed recently that a flavonoid antioxidant silymarin inhibits erbB 1 activation followed by a G 1 arrest...

  2. Flavonoids of Otanthus maritimus and Achillea santolina Growing in Egypt

    OpenAIRE

    AHMED A. SELF, EL-DIN; AMINA A., ABOU-DONIA; MINEO, SHIMIZU; Faculty of Pharmacy, Alexandria University; Faculty of Pharmacy, Alexandria University; Faculty of Pharmaceutical Sciences, Toyama Medical abd Pharmaceutical University

    1986-01-01

    From aerial parts of Otanthus maritimus and Achillea santolina plants, six flavonoids were isolated and identified viz., 3-methoxysalvigenin, artemetin, casticin and acacetin from O. maritimus and salvigenin, artemetin and eupatorin from A. santolina.

  3. Isolation and identification of flavonoids from anticancer and ...

    African Journals Online (AJOL)

    Isolation and identification of flavonoids from anticancer and neuroprotective extracts of Trigonella foenum graecum. Shabina Ishtiaq Ahmed, Muhammad Qasim Hayat, Saadia Zahid, Muhammad Tahir, Qaisar Mansoor, Muhammad Ismail, Kristen Keck, Robert Bates ...

  4. 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...... change in dose. The urinary excretion of ten dietary flavonoids was analysed after enzymatic hydrolysis by LC-MS and associated to the risk of ACS in a nested case-control study with 393 case-noncase pairs. The 393 case-noncase pairs were identified in the Danish Diet, Cancer and Health cohort comprising...... that the study was too limited in size to account for the variation associated with quantifying flavonoids in spot-urine samples. However, the non-monotonic, but statistically significant, association between higher kaempferol excretion and lower risk of ACS indicate that the lack of associations were not due...

  5. Study the active site of flavonoid applying radiation chemistry

    Energy Technology Data Exchange (ETDEWEB)

    Wu Jilan; Sun Gang; Zhang Fugen; He Yongke; Li Jiuqiang [Department of Technical Physics, Peking Univ., Beijing (China)

    2000-03-01

    Flavonoid are a large and important class of naturally occurring, low molecular weight benzo-{gamma}-pyrone derivatives which are reported to have a myriad of biological activities, but the study on the active sites of flavonoids is still ambiguous. In this paper, rutin, quercetin and baicalin have been selected as model compounds. It is well known that rutin is used in inhibiting arteriosclerosis and baicalin is antibacterial and antiviral. They have similar basic structure, but their medicinal properties are so different, why? As most flavonoids contain carbonyl group, which can capture electron effectively, we predict that flavonoids can capture electron to form radical anion. The formation of anion radical may have influence on the mitochondrial electron transport chain. The difference in the ability of forming anion radical may cause the difference in their medicinal effects. (author)

  6. Two new flavonoids from the bark of Allium chrysanthum.

    Science.gov (United States)

    Hu, Xing-Peng; Zhou, Hua; Du, Yang-Min; Ou, Shi-Yi; Yan, Rian; Wang, Yong

    2017-03-01

    The isolation and structure elucidation of two new flavonoids, chrysanthumones A and B from the extracts of Allium chrysanthum were reported. Seven known phenolic constituents were also isolated. Their structures were determined on the basis of NMR and MS techniques.

  7. Cupric ion reducing antioxidant capacity assay for food antioxidants: vitamins, polyphenolics, and flavonoids in food extracts.

    Science.gov (United States)

    Apak, Reşat; Güçlü, Kubilay; Ozyürek, Mustafa; Bektas Oğlu, Burcu; Bener, Mustafa

    2008-01-01

    Antioxidants are health beneficial compounds through their combat with reactive oxygen and nitrogen species and free radicals that may cause tissue damage leading to various diseases. This work reports the development of a simple and widely applicable antioxidant capacity index for dietary polyphenols, vitamins C and E, and plasma antioxidants utilizing the copper(II)-neocuproine (Cu(II)-Nc) reagent as the chromogenic oxidizing agent. This novel method based on an electron-transfer mechanism was named by our research group as 'cupric reducing antioxidant capacity', abbreviated as the CUPRAC method. The method is comprised of mixing the antioxidant solution with aqueous copper(II) chloride, alcoholic neocuproine, and ammonium acetate aqueous buffer at pH 7, and subsequently measuring the developed absorbance at 450 nm after 30 min. Since the color development is fast for compounds like ascorbic acid, gallic acid, and quercetin but slow for naringin and naringenin, the latter compounds are assayed after incubation at 50 degrees C on a water bath for 20 min. The flavonoid glycosides are hydrolyzed to their corresponding aglycones by refluxing in 1.2 M: HCl-containing 50% MeOH so as to exert maximal reducing power towards Cu(II)-Nc. The CUPRAC antioxidant capacities of synthetic mixtures are equal to the sum of individual capacities of antioxidant constituents, indicating lack of chemical deviations from Beer's law. Tests on antioxidant polyphenols demonstrate that the highest CUPRAC capacities are observed for epicatechin gallate, epigallocatechin gallate, quercetin, fisetin, epigallocatechin, catechin, and caffeic acid in this order, in accord with the number and position of the -OH groups as well the conjugation level of the molecule. The parallelism of the linear calibration curves of pure antioxidants in water and in a given complex matrix (plant extract) demonstrates that there are no chemical interactions of interferent nature among the solution constituents

  8. Comparative Developmental Toxicity of Flavonoids Using an Integrative Zebrafish System.

    Science.gov (United States)

    Bugel, Sean M; Bonventre, Josephine A; Tanguay, Robert L

    2016-11-01

    Flavonoids are a large, structurally diverse class of bioactive naturally occurring chemicals commonly detected in breast milk, soy based infant formulas, amniotic fluid, and fetal cord blood. The potential for pervasive early life stage exposures raises concerns for perturbation of embryogenesis, though developmental toxicity and bioactivity information is limited for many flavonoids. Therefore, we evaluated a suite of 24 flavonoid and flavonoid-like chemicals using a zebrafish embryo-larval toxicity bioassay-an alternative model for investigating developmental toxicity of environmentally relevant chemicals. Embryos were exposed to 1-50 µM of each chemical from 6 to 120 h postfertilization (hpf), and assessed for 26 adverse developmental endpoints at 24, 72, and 120 hpf. Behavioral changes were evaluated in morphologically normal animals at 24 and 72 hpf, at 120 hpf using a larval photomotor response (LPR) assay. Gene expression was comparatively evaluated for all compounds for effects on biomarker transcripts indicative of AHR (cyp1a) and ER (cyp19a1b, esr1, lhb, vtg) pathway bioactivity. Overall, 15 of 24 flavonoids elicited adverse effects on one or more of the developmental or behavioral endpoints. Hierarchical clustering and principle component analyses compared toxicity profiles and identified 3 distinct groups of bioactive flavonoids. Despite robust induction of multiple estrogen-responsive biomarkers, co-exposure with ER and GPER antagonists did not ameliorate toxicity, suggesting ER-independence and alternative modes of action. Taken together, these studies demonstrate that development is sensitive to perturbation by bioactive flavonoids in zebrafish that are not related to traditional estrogen receptor mode of action pathways. This integrative zebrafish platform provides a useful framework for evaluating flavonoid developmental toxicity and hazard prioritization. © The Author 2016. Published by Oxford University Press on behalf of the Society of

  9. Acylated flavonoid and phenylethanoid glycosides from Marrubium velutinum.

    Science.gov (United States)

    Karioti, Anastasia; Skaltsa, Helen; Heilmann, Jörg; Sticher, Otto

    2003-09-01

    From the aerial parts of Marrubium velutinum, one acylated flavonoid glycoside, chrysoeriol 7-O-(3",6"-di-O-E-p-coumaroyl)-beta-D-glucopyranoside, and two tetrasaccharidic phenylethanoid glycosides, velutinosides I-II, have been isolated together with ten known flavonoids and seven known phenylethanoid glycosides. The structures of the isolated compounds were established by means of NMR, MS, and UV spectral analyses.

  10. Dietary flavonoid intake and risk of stomach and colorectal cancer.

    Science.gov (United States)

    Woo, Hae Dong; Kim, Jeongseon

    2013-02-21

    Stomach and colorectal cancers are common cancers and leading causes of cancer deaths. Because the alimentary tract can interact directly with dietary components, stomach and colorectal cancer may be closely related to dietary intake. We systematically searched published literature written in English via PubMed by searching for terms related to stomach and colorectal cancer risk and dietary flavonoids up to June 30, 2012. Twenty-three studies out of 209 identified articles were finally selected for the analysis. Log point effect estimates and the corresponding standard errors were calculated using covariate-adjusted point effect estimates and 95%CIs from the selected studies. Total dietary flavonoid intake was not associated with a reduced risk of colorectal or stomach cancer [odds ratio (OR) (95%CI) = 1.00 (0.90-1.11) and 1.07 (0.70-1.61), respectively]. Among flavonoid subclasses, the intake of flavonols, flavan-3-ols, anthocyanidins, and proanthocyanidins showed a significant inverse association with colorectal cancer risk [OR (95%CI) = 0.71 (0.63-0.81), 0.88 (0.79-0.97), 0.68 (0.56-0.82), and 0.72 (0.61-0.85), respectively]. A significant association was found only between flavonols and stomach cancer risk based on a limited number of selected studies [OR (95%CI) = 0.68 (0.46-0.99)]. In the summary estimates from case-control studies, all flavonoid subclasses except flavones and flavanones were inversely associated with colorectal cancer risk, whereas neither total flavonoids nor any subclasses of flavonoids were associated with colorectal cancer risk in the summary estimates based on the cohort studies. The significant association between flavonoid subclasses and cancer risk might be closely related to bias derived from the case-control design. There was no clear evidence that dietary flavonoids are associated with reduced risk of stomach and colorectal cancer.

  11. Separation and identification of phenolic compounds of extra virgin olive oil from Olea europaea L. by HPLC-DAD-SPE-NMR/MS. Identification of a new diastereoisomer of the aldehydic form of oleuropein aglycone.

    Science.gov (United States)

    Pérez-Trujillo, Míriam; Gómez-Caravaca, Ana María; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto; Parella, Teodor

    2010-08-25

    The phenolic fraction of a monovarietal extra virgin olive oil (EVOO) from Olea europaea L. var. Cornezuelo was studied by the hyphenated HPLC-DAD-SPE-NMR/MS techniques. This survey led to the identification of 25 main compounds. One was identified as a new diastereoisomer of the aldehydic form of oleuropein aglycone (AOA) and characterized by 1D and 2D NMR techniques. The relative configuration of this new AOA was determined as 5R*,8S*,9S* on the basis of the results obtained from the combination of NOE experiments and Monte Carlo conformational search calculations. Assuming, as for the described diastereoisomers, that the new AOA comes from the natural oleuropein aglycone (OA), the absolute configuration was proposed as 5S,8R,9R.

  12. A conformational NMR analysis of methymycin aglycones: complete and unambiguous assignments of stereochemically diverse glycosylated methymycin analogs by 1D and 2D NMR techniques and molecular modeling.

    Science.gov (United States)

    Akhmedov, Novruz G; Gannett, Peter M; Wu, Bulan; Cummings, Matthew M; Train, Brian C

    2013-03-01

    The (1)H and (13)C NMR spectra of 10-deoxymethynolide (1), 8.9-dihydro-10-deoxymethynolide (2) and its glycosylated derivatives (3-9) were analyzed using gradient-selected NMR techniques, including 1D TOCSY, gCOSY, 1D NOESY (DPFGSENOE), NOESY, gHMBC, gHSQC and gHSQC-TOCSY. The NMR spectral parameters (chemical shifts and coupling constants) of 1-9 were determined by iterative analysis. For the first time, complete and unambiguous assignment of the (1)H NMR spectrum of 10-deoxymethynolide (1) has been achieved in CDCl(3), CD(3)OD and C(6)D(6) solvents. The (1)H NMR spectrum of 8,9-dihydro-10-deoxymethynolide (2) was recorded in CDCl(3), (CD(3))(2)CO and CD(3)OD solutions to determine the conformation. NMR-based conformational analysis of 1 and 2 in conjugation with molecular modeling concluded that the 12-membered ring of the macrolactones may predominantly exist in a single stable conformation in all solvents examined. In all cases, a change in solvent caused only small changes in chemical shifts and coupling constants, suggesting that all glycosylated methymycin analogs exist with similar conformations of the aglycone ring in solution. Copyright © 2013 John Wiley & Sons, Ltd.

  13. Skim milk powder supplementation affects lactose utilization, microbial survival and biotransformation of isoflavone glycosides to isoflavone aglycones in soymilk by Lactobacillus.

    Science.gov (United States)

    Pham, Thuy T; Shah, Nagendra P

    2008-08-01

    Four probiotic bacteria, Lactobacillus acidophilus 4461, L. acidophilus 4962, Lactobacillus casei 290 and L. casei 2607, were used for fermentation of soymilk (SM) prepared from soy protein isolate (SPI) supplemented with skim milk powder (SMP) (SSM). Soymilk and reconstituted skim milk (RSM) were used as controls. Lactose utilization in SSM by these probiotic organisms ranged from 14.97 to 18.15mg/ml, compared to 14.12-16.06mg/ml for RSM. The pH in SSM dropped to 4.07-4.29 compared to 6.15-6.36 for SM and 4.10-4.96 for RSM. The microbial viable counts were also significantly enhanced by up to 0.98logCFU/ml by the supplementation of SMP to SM. The biotransformation level of isoflavone glycosides (IG) to isoflavone aglycones (IA) in SSM ranged from 81.4% to 85.1%, which was 13.9-19.0% higher than that for SM, after 24h of incubation. Most of IG in SSM was completely converted to IA, except malonyl glycitin and malonyl genistin. At the end of the incubation, IA comprised up to 76.8% of total isoflavones in SSM.

  14. A versatile, stability-indicating and high-throughput ultra-fast liquid chromatography method for the determination of isoflavone aglycones in soybeans, topical formulations, and permeation assays.

    Science.gov (United States)

    Nemitz, Marina C; Yatsu, Francini K J; Bidone, Juliana; Koester, Letícia S; Bassani, Valquiria L; Garcia, Cássia V; Mendez, Andreas S L; von Poser, Gilsane L; Teixeira, Helder F

    2015-03-01

    There is a growing interest in the pharmaceutical field concerning isoflavones topical delivery systems, especially with regard to their skin care properties and antiherpetic activity. In this context, the present work describes an ultra-fast liquid chromatography method (UFLC) for determining daidzein, glycitein, and genistein in different matrices during the development of topical systems containing isoflavone aglycones (IA) obtained from soybeans. The method showed to be specific, precise, accurate, and linear (0.1 to 5 µg mL(-1)) for IA determination in soybean acid extract, IA-rich fraction obtained after the purification process, IA loaded-nanoemulsions, and topical hydrogel, as well as for permeation/retention assays in porcine skin and porcine esophageal mucosa. The matrix effect was determined for all complex matrices, demonstrating low effect during the analysis. The stability indicating UFLC method was verified by submitting IA to acidic, alkaline, oxidative, and thermal stress conditions, and no interference of degradation products was detected during analysis. Mass spectrometry was performed to show the main compounds produced after acid hydrolysis of soybeans, as well as suggest the main degradation products formed after stress conditions. Besides the IA, hydroxymethylfurfural and ethoxymethylfurfural were produced and identified after acid hydrolysis of the soybean extract and well separated by the UFLC method. The method's robustness was confirmed using the Plackett-Burman experimental design. Therefore, the new method affords fast IA analysis during routine processes, extract purification, products development, and bioanalytical assays. Copyright © 2014 Elsevier B.V. All rights reserved.

  15. Photoprotective properties of 20(S)-protopanaxatriol, an aglycone of ginseng saponins: Protection from ultraviolet-B radiation-induced oxidative stress in human epidermal keratinocytes.

    Science.gov (United States)

    Oh, Sun-Joo; Kim, Kyunghoon; Lim, Chang-Jin

    2016-09-01

    Ginsenosides are responsible for diverse pharmacological properties ascribed to ginseng, a plant used in traditional medicine. Ginsenosides are classified into three categories: Protopanaxadiol, protopanaxatriol (PPT) and oleanolic acid. As an aglycone of PPT-type ginsenosides, PPT exists in two stereoisomeric forms, 20(S)-PPT and 20(R)‑PPT. The 20(S)‑PPT stereoisomer is a major metabolic product of PPT‑type ginsenosides produced in the gastrointestinal tract. In the present study, 20(S)-PPT suppressed the elevation of reactive oxygen species in HaCaT cells following irradiation with ultraviolet (UV)‑B. In addition, 20(S)‑PPT inhibited UV‑B‑induced gelatinase activities of matrix metalloproteinase-2 and -9 in HaCaT cells, and suppressed UV‑B‑induced expression and secretion of these proteins. Accordingly, 20(S)‑PPT restored the total glutathione levels in UV‑B‑irradiated keratinocytes. Taken together, these data indicated that 20(S)‑PPT may possess photoprotective properties that combat the effects of UV‑B radiation.

  16. Enhanced Production of Two Bioactive Isoflavone Aglycones in Astragalus membranaceus Hairy Root Cultures by Combining Deglycosylation and Elicitation of Immobilized Edible Aspergillus niger.

    Science.gov (United States)

    Jiao, Jiao; Gai, Qing-Yan; Niu, Li-Li; Wang, Xi-Qing; Guo, Na; Zang, Yu-Ping; Fu, Yu-Jie

    2017-10-18

    A cocultivation system of Astragalus membranaceus hairy root cultures (AMHRCs) and immobilized food-grade fungi was established for the enhanced production of calycosin (CA) and formononetin (FO). The highest accumulations of CA (730.88 ± 63.72 μg/g DW) and FO (1119.42 ± 95.85 μg/g DW) were achieved in 34 day-old AMHRCs cocultured with immobilized A. niger (IAN) for 54 h, which were 7.72- and 18.78-fold higher than CA and FO in nontreated control, respectively. IAN deglycosylation could promote the formation of CA and FO by conversion of their glycoside precursors. IAN elicitation could intensify the generation of endogenous signal molecules involved in plant defense response, which contributed to the significantly up-regulated expression of genes in CA and FO biosynthetic pathway. Overall, the coupled culture of IAN and AMHRCs offered a promising and effective in vitro approach to enhance the production of two health-promoting isoflavone aglycones for possible nutraceutical and pharmaceutical uses.

  17. Purification of Flavonoids from Black Currant Juice by Nanodiafiltration

    DEFF Research Database (Denmark)

    Jensen, Morten Busch; Christensen, Knud Villy; Norddahl, Birgir

    2009-01-01

      Various compounds of the flavonoid group have been reported to possess therapeutic effects towards cancer [1]. Thus there is a large potential in identifying, purifying and quantifying flavonoids from different natural sources in order to screen the pharmaceutical values of these. The flavonoids...... are normally present in much smaller quantities than other solutes such as sugars and organic acids. This may state a problem in analysis as some of the flavonoids are present in very minute amounts and concentration is limited by the major solutes. This study seeks to separate the sugars and organic acids...... from the flavonoids in order to facilitate better analysis.         In the current study, the major solutes in black currant juice are fructose (32 ± 3 g/l), glucose (22 ± 3 g/l), sucrose (1.6 ± 0.2 g/l) and organic acids (28.9 ± 0.1 g/l). The flavonoids in black currant juice are mainly (97...

  18. Plant flavonoids in cancer chemoprevention: role in genome stability.

    Science.gov (United States)

    George, Vazhappilly Cijo; Dellaire, Graham; Rupasinghe, H P Vasantha

    2017-07-01

    Carcinogenesis is a multistage process that involves a series of events comprising of genetic and epigenetic changes leading to the initiation, promotion and progression of cancer. Chemoprevention is referred to as the use of nontoxic natural compounds, synthetic chemicals or their combinations to intervene in multistage carcinogenesis. Chemoprevention through diet modification, i.e., increased consumption of plant-based food, has emerged as a most promising and potentially cost-effective approach to reducing the risk of cancer. Flavonoids are naturally occurring polyphenols that are ubiquitous in plant-based food such as fruits, vegetables and teas as well as in most medicinal plants. Over 10,000 flavonoids have been characterized over the last few decades. Flavonoids comprise of several subclasses including flavonols, flavan-3-ols, anthocyanins, flavanones, flavones, isoflavones and proanthocyanidins. This review describes the most efficacious plant flavonoids, including luteolin, epigallocatechin gallate, quercetin, apigenin and chrysin; their hormetic effects; and the molecular basis of how these flavonoids contribute to the chemoprevention with a focus on protection against DNA damage caused by various carcinogenic factors. The present knowledge on the role of flavonoids in chemoprevention can be used in developing effective dietary strategies and natural health products targeted for cancer chemoprevention. Copyright © 2016 Elsevier Inc. All rights reserved.

  19. Analytical methods for quantitation of prenylated flavonoids from hops

    Science.gov (United States)

    Nikolić, Dejan; van Breemen, Richard B.

    2013-01-01

    The female flowers of hops (Humulus lupulus L.) are used as a flavoring agent in the brewing industry. There is growing interest in possible health benefits of hops, particularly as estrogenic and chemopreventive agents. Among the possible active constituents, most of the attention has focused on prenylated flavonoids, which can chemically be classified as prenylated chalcones and prenylated flavanones. Among chalcones, xanthohumol (XN) and desmethylxanthohumol (DMX) have been the most studied, while among flavanones, 8-prenylnaringenin (8-PN) and 6-prenylnaringenin (6-PN) have received the most attention. Because of the interest in medicinal properties of prenylated flavonoids, there is demand for accurate, reproducible and sensitive analytical methods to quantify these compounds in various matrices. Such methods are needed, for example, for quality control and standardization of hop extracts, measurement of the content of prenylated flavonoids in beer, and to determine pharmacokinetic properties of prenylated flavonoids in animals and humans. This review summarizes currently available analytical methods for quantitative analysis of the major prenylated flavonoids, with an emphasis on the LC-MS and LC-MS-MS methods and their recent applications to biomedical research on hops. This review covers all methods in which prenylated flavonoids have been measured, either as the primary analytes or as a part of a larger group of analytes. The review also discusses methodological issues relating to the quantitative analysis of these compounds regardless of the chosen analytical approach. PMID:24077106

  20. Structure-Activity Association of Flavonoids in Lung Diseases

    Directory of Open Access Journals (Sweden)

    João Henrique G. Lago

    2014-03-01

    Full Text Available Flavonoids are polyphenolic compounds classified into flavonols, flavones, flavanones, isoflavones, catechins, anthocyanidins, and chalcones according to their chemical structures. They are abundantly found in Nature and over 8,000 flavonoids have from different sources, mainly plant materials, have been described. Recently reports have shown the valuable effects of flavonoids as antiviral, anti-allergic, antiplatelet, antitumor, antioxidant, and anti-inflammatory agents and interest in these compounds has been increasing since they can be helpful to human health. Several mechanisms of action are involved in the biological properties of flavonoids such as free radical scavenging, transition metal ion chelation, activation of survival genes and signaling pathways, regulation of mitochondrial function and modulation of inflammatory responses. The anti-inflammatory effects of flavonoids have been described in a number of studies in the literature, but not frequently associated to respiratory disease. Thus, this review aims to discuss the effects of different flavonoids in the control of lung inflammation in some disorders such as asthma, lung emphysema and acute respiratory distress syndrome and the possible mechanisms of action, as well as establish some structure-activity relationships between this biological potential and chemical profile of these compounds.

  1. The response of filamentous fungus Rhizopus nigricans to flavonoids.

    Science.gov (United States)

    Slana, Marko; Zigon, Dušan; Makovec, Tomaž; Lenasi, Helena

    2011-08-01

    The saprophytic fungus Rhizopus nigricans constitutes a serious problem when thriving on gathered crops. The identification of any compounds, especially natural ones, that inhibit fungal growth, may therefore be important. During its life cycle, Rhizopus nigricans encounters many compounds, among them the flavonoids, plant secondary metabolites that are involved in plant defense against pathogenic microorganisms. Although not being a plant pathogen, Rhizopus nigricans may interact with these compounds in the same way as plant pathogens--in response to the fungitoxic effect of flavonoids the fungi transform them into less toxic metabolites. We have studied the interaction of R. nigricans with some flavonoids. Inhibition of hyphal spreading (from 3% to 100%) was observed by 300 μM flavones, flavanones and isoflavones, irrespective of their basic structure, oxidized or reduced C-ring, and orientation of the B-ring. However, a hydrophobic A-ring was important for the toxicity. R. nigricans transformed some of the flavonoids into glucosylated products. Recognition of substrates for glucosylating enzyme(s) did not correlate with their fungitoxic effect but depended exclusively on the presence of a free -OH group in the flavonoid A-ring and of a hydrophobic B-ring. Although the fungus produced glucosyltransferase constitutively, an additional amount of the enzyme was induced by the substrate flavonoid. Moreover, effective detoxification was shown to require the presence of glucose. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  2. Flavonoids and sesquiterpenes of Croton pedicellatus Kunth; Flavonoides e sesquiterpenos de Croton pedicellatus Kunth.

    Energy Technology Data Exchange (ETDEWEB)

    Lopes, Elton Luz; Andrade Neto, Manoel; Silveira, Edilberto Rocha; Pessoa, Otilia Deusdenia Loiola [Universidade Federal do Ceara (UFC), Fortaleza, CE (Brazil). Dept. de Quimica Organica e Inorganica; Braz-Filho, Raimundo [Universidade Estadual do Norte Fluminense (UENF), Campos dos Goytacases, RJ (Brazil). Dept. de Quimica

    2012-07-01

    The chemical investigation of the ethanolic extract from leaves of Croton pedicellatus yielded the bis-nor-sesquiterpenes blumenol A and blumenol A glucoside, along with the flavonoids: tiliroside, 6{sup -}O-p-coumaroyl-{beta}-galactopyranosyl- kaempferol, 6{sup -}O-p-coumaroyl-{beta}-glucopyranosyl-3{sup -}methoxy- kaempferol, kaempferol, 3-glucopyranosyl-quercetin and alpinumisoflavone, as well as 4-hydroxy-3,5-dimethoxybenzoic acid. The identification of all isolated compounds was performed by spectrometric methods, including HR-ESI-MS, 1D and 2D NMR experiments, and by comparison with previously-described physical and spectral data. (author)

  3. Ultrathin films of lipids to investigate the action of a flavonoid with cell membrane models.

    Science.gov (United States)

    Ferrreira, João Victor Narducci; Grecco, Simone Dos S; Lago, João Henrique G; Caseli, Luciano

    2015-03-01

    Understanding the role of natural compounds whose pharmaceutical activity is associated with cell membranes is fundamental to comprehending the biochemical processes that occur on membrane surfaces. In this work, we examined the action of 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one, known as quercetin, QCT, in lipid Langmuir monolayers at the air-water interface, which served as a model for half of a membrane. The surface pressure-area isotherms for 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) lipid monolayers exhibited a noticeable shift to higher areas in the presence of the flavonoid, which indicated the incorporation of QCT into the monolayer and expansion of the film. Also the flavonoid incorporation diminishes the monolayer surface elasticity for DPPC and causes a relative decrease of the intensity for C-H stretch bands, pointing to a disruption of the packed order of DPPC. These results can be associated to the interaction between QCT and cell membrane surfaces during biochemical processes, which may influence its pharmaceutical properties. Copyright © 2014 Elsevier B.V. All rights reserved.

  4. Inhibition of transmembrane member 16A calcium-activated chloride channels by natural flavonoids contributes to flavonoid anticancer effects.

    Science.gov (United States)

    Zhang, Xuan; Li, Honglin; Zhang, Huiran; Liu, Yani; Huo, Lifang; Jia, Zhanfeng; Xue, Yucong; Sun, Xiaorun; Zhang, Wei

    2017-07-01

    Natural flavonoids are ubiquitous in dietary plants and vegetables and have been proposed to have antiviral, antioxidant, cardiovascular protective and anticancer effects. Transmembrane member 16A (TMEM16A)-encoded Ca 2+ -activated Cl - channels play a variety of physiological roles in many organs and tissues. Overexpression of TMEM16A is also believed to be associated with cancer progression. Therefore, inhibition of TMEM16A current may be a potential target for cancer therapy. In this study, we screened a broad spectrum of flavonoids for their inhibitory activities on TMEM16A currents. A whole-cell patch technique was used to record the currents. The BrdU assay and transwell technique were used to investigate cell proliferation and migration. At a concentration of 100 μM, 10 of 20 compounds caused significant (>50%) inhibition of TMEM16A currents. The four most potent compounds - luteolin, galangin, quercetin and fisetin - had IC 50 values ranging from 4.5 to 15 μM). To examine the physiological relevance of these findings, we also studied the effects of these flavonoids on endogenous TMEM16A currents in addition to cell proliferation and migration in LA795 cancer cells. Among the flavonoids tested, we detected a highly significant correlation between TMEM16A current inhibition and cell proliferation or reduction of migration. This study demonstrates that flavonoids inhibit TMEM16A currents and suggests that flavonoids could have anticancer effects via this mechanism. © 2017 The British Pharmacological Society.

  5. Flavonoids of Lotus (Nelumbo nucifera) Seed Embryos and Their Antioxidant Potential.

    Science.gov (United States)

    Zhu, Mingzhi; Liu, Ting; Zhang, Chunyun; Guo, Mingquan

    2017-08-01

    Flavonoids from lotus (Nelumbo nucifera) seed embryos were fractionated over a macroporous resin chromatography into 2 main fractions (I and II), and subsequently identified by high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS 2 ). Sixteen flavonoids were identified in lotus seed embryos, including 8 flavonoid C-glycosides and 8 flavonoid O-glycosides, in which the flavonoid C-glycosides were the main flavonoids. Among them, 2 flavonoid O-glycosides (luteolin 7-O-neohesperidoside and kaempferol 7-O-glucoside) were identified in lotus seed embryos for the 1st time. For further elucidating the effects of flavonoid C-glycosides to the bioactivities of lotus seed embryos, we compared the differences of the flavonoids and their antioxidant activities between leaves and seed embryos of lotus using the same methods. The results showed the antioxidant activity of flavonoids in lotus seed embryos was comparable or higher than that in lotus leaves, whereas the total flavonoid content in seed embryos was lower than lotus leaves which only contained flavonoid O-glycosides. The flavonoid C-glycosides of lotus seed embryos had higher antioxidant properties than the flavonoid O-glycosides presented in lotus leaves. This study suggested that the lotus seed embryos could be promising sources with antioxidant activity and used as dietary supplements for health promotion. © 2017 Institute of Food Technologists®.

  6. Enhancing Human Cognition with Cocoa Flavonoids

    Directory of Open Access Journals (Sweden)

    Valentina Socci

    2017-05-01

    Full Text Available Enhancing cognitive abilities has become a fascinating scientific challenge, recently driven by the interest in preventing age-related cognitive decline and sustaining normal cognitive performance in response to cognitively demanding environments. In recent years, cocoa and cocoa-derived products, as a rich source of flavonoids, mainly the flavanols sub-class, have been clearly shown to exert cardiovascular benefits. More recently, neuromodulation and neuroprotective actions have been also suggested. Here, we discuss human studies specifically aimed at investigating the effects of acute and chronic administration of cocoa flavanols on different cognitive domains, such as executive functions, attention and memory. Through a variety of direct and indirect biological actions, in part still speculative, cocoa and cocoa-derived food have been suggested to possess the potential to counteract cognitive decline and sustain cognitive abilities, particularly among patients at risk. Although still at a preliminary stage, research investigating the relations between cocoa and cognition shows dose-dependent improvements in general cognition, attention, processing speed, and working memory. Moreover, cocoa flavanols administration could also enhance normal cognitive functioning and exert a protective role on cognitive performance and cardiovascular function specifically impaired by sleep loss, in healthy subjects. Together, these findings converge at pointing to cocoa as a new interesting nutraceutical tool to protect human cognition and counteract different types of cognitive decline, thus encouraging further investigations. Future research should include complex experimental designs combining neuroimaging techniques with physiological and behavioral measures to better elucidate cocoa neuromodulatory properties and directly compare immediate versus long-lasting cognitive effects.

  7. Inhibition effect on lipid oxidation of irradiated pork by adding hawthorn flavonoid extract

    International Nuclear Information System (INIS)

    Wang Xiaoming; Liu Chao; Cao Lei; Li Kexi

    2011-01-01

    The antioxidant activity of hawthorn flavonoid extract and its inhibition effect on irradiated pork lipid oxidant were investigated. The results showed that hawthorn flavonoids had efficient scavenging effect on DPPH free radicals (DPPH ·), and the scavenging rate reached 56% while 2 ml of 0.035 mg/ml hawthorn flavonoid extract was added. Hawthorn flavonoid extract can inhibition the lipid oxidation of irradiated pork effectively and it showed a stronger inhibition ability while the hawthorn flavonoid extract were used together with Vc. It is concluded that can decrease the lipid oxidation of pork, hawthorn flavonoid extract is a remarkable natural antioxidant. (authors)

  8. Application of the Suzuki-Miyaura Reaction in the Synthesis of Flavonoids

    Directory of Open Access Journals (Sweden)

    Fanie R. Van Heerden

    2013-04-01

    Full Text Available The application of the Suzuki-Miyaura reaction in the synthesis of flavonoids, an important class of natural products, is reviewed. This reaction has not only been employed to provide access to flavonoid nuclei, but has also been applied to the synthesis of dimeric flavonoids and in the synthesis of libraries of flavonoid derivatives for biological activity studies. The classes of flavonoids that are discussed are the chalcones, flavones, isoflavones, neoflavones, biflavones and derivatives of flavonoids obtained by C-C bond formation via the Suzuki-Miyaura reaction.

  9. Phytochemical studies of flavonoids from polygonum glabrum L of Sudan

    International Nuclear Information System (INIS)

    Mohammed, Intisar Sirour

    1996-01-01

    A semi- aquatic plant, Polygnum glabrum wild of the family polygonaceae was reported in traditional medicine of Sudan as anthelmintic and as a remedy against intestinal colics.The literature reported the isolation and structure elucidation of the bioactive agents as being sequi terpenes. The flavonoids of the Sudanese species were not investigated before. The present work consisted of phyto chemical study of the leaves of Polygonum galbrum wild. Before experimentation, a through authentication of the plant was done to correct previously reported errors. In the first stages a phyto chemical screening was made which confirmed the presence of flavonoid compounds in higher amounts than the other classes of natural products present in the plant. Different chromatographic techniques of isolation were assayed but the fractionation of flavonoids was successfully done with preparative thin layer chromatographic techniques. Yellow crystals, namely (two compounds) were obtained in pure form and identified as being flavonoids. Spectral studies were performed on Infra-Red and Ultra- Violet spectrophotometers. The computerized Ultra- Violet spectrophotometer allowed us to obtain complete data about the studied compounds. Structure elucidation was attempted and the structure of the isolated flavonoids were suggested as being Isorhamnetin and Diosmetin. (Author)

  10. Antioxidant and Hepatoprotective Activities of Flavonoids from Bauhinia hookeri

    Directory of Open Access Journals (Sweden)

    Eman Al-Sayed

    2016-05-01

    Full Text Available In a previous study, the total ethanol extract of Bauhinia hookeri showed a significant hepatoprotective effect in CCl 4-induced toxicity model in mice. However, the active components responsible for the activity were not identified. Therefore, this study was undertaken to determine if the activity of B. hookeri extract is due to its flavonoid content. The hepatoprotective activity of B. hookeri flavonoids was determined by measuring the activities of alanine aminotransferase (ALT and aspartate aminotransferase (AST in the culture medium of HepG2 cells challenged with CCl 4. The lipid peroxidation and antioxidant parameters, superoxide dismutase (SOD and glutathione (GSH were estimated in the cell lysates. The isolated flavonoids were identified by mass, UV and NMR spectral data. This study revealed that B. hookeri flavonoid fraction and its pure compounds ( kaempferol 3-O-β- D-glucoside, quercetin 3-O-β- D-glucoside and c atechin 3-O-α- L-rhamnoside possess a promising hepatoprotective activity as evidenced from the normalized levels of ALT and AST. This was attributed partly to their potent antioxidant activity as demonstrated by the increased GSH levels, SOD activity and reduced lipid peroxidation. The whole flavonoid fraction showed the highest cytoprotective activity and was more effective than silymarin. This study highlights a promising natural hepatoprotective remedy derived from B. hookeri.

  11. Flavonoids, Thyroid Iodide Uptake and Thyroid Cancer-A Review.

    Science.gov (United States)

    Gonçalves, Carlos F L; de Freitas, Mariana L; Ferreira, Andrea C F

    2017-06-12

    Thyroid cancer is the most common malignant tumor of the endocrine system and the incidence has been increasing in recent years. In a great part of the differentiated carcinomas, thyrocytes are capable of uptaking iodide. In these cases, the main therapeutic approach includes thyroidectomy followed by ablative therapy with radioiodine. However, in part of the patients, the capacity to concentrate iodide is lost due to down-regulation of the sodium-iodide symporter (NIS), the protein responsible for transporting iodide into the thyrocytes. Thus, therapy with radioiodide becomes ineffective, limiting therapeutic options and reducing the life expectancy of the patient. Excessive ingestion of some flavonoids has been associated with thyroid dysfunction and goiter. Nevertheless, studies have shown that some flavonoids can be beneficial for thyroid cancer, by reducing cell proliferation and increasing cell death, besides increasing NIS mRNA levels and iodide uptake. Recent data show that the flavonoids apingenin and rutin are capable of increasing NIS function and expression in vivo. Herein we review literature data regarding the effect of flavonoids on thyroid cancer, besides the effect of these compounds on the expression and function of the sodium-iodide symporter. We will also discuss the possibility of using flavonoids as adjuvants for therapy of thyroid cancer.

  12. Non-alcoholic Fatty Liver Disease: Beneficial Effects of Flavonoids.

    Science.gov (United States)

    Akhlaghi, Masoumeh

    2016-10-01

    Non-alcoholic fatty liver disease (NAFLD) has been known as the hepatic feature of metabolic syndrome. Extra fat depots, especially in visceral areas, develop insulin resistance as a result of mild oxidation and inflammation. Insulin resistance induces lipolysis and releases free fatty acids into the circulation, where they are transported to the liver. In the liver, free fatty acids are converted to triglycerides and accumulate, causing simple steatosis that, if left untreated, can lead to steatohepatitis, and subsequently liver necrosis and cirrhosis.Flavonoids, a group of plant compounds with incredible biological characteristics, have shown advantages in pathological conditions. Beneficial effects of flavonoids against NAFLD and its related disorders have been observed in both animal and human studies. Various mechanisms have been found for their protection. Flavonoids prevent hepatosteatosis by increasing fatty acid oxidation in the liver. They can also reduce caloric intake and decrease body weight and fat deposition in visceral tissues. Flavonoids are unique antioxidants that exert their beneficial effects through inhibition of nuclear factor κB, thereby attenuating release of inflammatory cytokines, which are triggers of insulin resistance. Finally, flavonoids have shown to increase adiponectin, improve insulin sensitivity and glucose tolerance, correct dyslipidemia, and reduce blood pressure in patients with NAFLD. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

  13. Chlorinated Flavonoids Modulate the Inflammatory Process in Human Blood.

    Science.gov (United States)

    Proença, Carina; Ribeiro, Daniela; Soares, Tânia; Tomé, Sara M; Silva, Artur M S; Lima, José L F C; Fernandes, Eduarda; Freitas, Marisa

    2017-08-01

    Flavonoids are known to react with neutrophil-generated hypochlorous acid (HOCl) at inflammation loci to form stable mono- and dichlorinated products. Some of these products have been shown to retain or even enhance their inflammatory potential, but further information is required in a broader approach to inflammatory mechanisms. In that sense, we performed an integrated evaluation on the anti-inflammatory potential of a panel of novel chlorinated flavonoids and their parent compounds, in several steps of the complex inflammatory cascade, namely, in the activity of cyclooxygenase (COX)-1 and COX-2, and in the production of cytokines [interleukin (IL)-6, IL-1β, tumor necrosis factor (TNF)], and the chemokine, IL-8, as well as in the production of reactive species, using human whole blood as a representative in vitro model, establishing, whenever possible, a structure-activity relationship. Although luteolin was the most active compound, chlorinated flavonoids demonstrated a remarkable pattern of activity for the resolution of the inflammatory processes. Our results demonstrated that 6-chloro-3',4',5,7-tetrahydroxyflavone deserves scientific attention due to its ability to modulate the reactive species and cytokines/chemokine production. In this regard, the therapeutic potential of flavonoids' metabolites, and in this particular case the chlorinated flavonoids, should not be neglected.

  14. Luteolin, a flavonoid, inhibits AP-1 activation by basophils

    International Nuclear Information System (INIS)

    Hirano, Toru; Higa, Shinji; Arimitsu, Junsuke; Naka, Tetsuji; Ogata, Atsushi; Shima, Yoshihito; Fujimoto, Minoru; Yamadori, Tomoki; Ohkawara, Tomoharu; Kuwabara, Yusuke; Kawai, Mari; Matsuda, Hisashi; Yoshikawa, Masayuki; Maezaki, Naoyoshi; Tanaka, Tetsuaki; Kawase, Ichiro; Tanaka, Toshio

    2006-01-01

    Flavonoids including luteolin, apigenin, and fisetin are inhibitors of IL-4 synthesis and CD40 ligand expression by basophils. This study was done to search for compounds with greater inhibitory activity of IL-4 expression and to clarify the molecular mechanisms through which flavonoids inhibit their expression. Of the 37 flavonoids and related compounds examined, ayanin, luteolin, and apigenin were the strongest inhibitors of IL-4 production by purified basophils in response to anti-IgE antibody plus IL-3. Luteolin did not suppress Syk or Lyn phosphorylation in basophils, nor did suppress p54/46 SAPK/JNK, p38 MAPK, and p44/42 MAPK activation by a basophilic cell line, KU812 cells, stimulated with A23187 and PMA. However, luteolin did inhibit phosphorylation of c-Jun and DNA binding activity of AP-1 in nuclear lysates from stimulated KU812 cells. These results provide a fundamental structure of flavonoids for IL-4 inhibition and demonstrate a novel action of flavonoids that suppresses the activation of AP-1

  15. Flavonoids, Thyroid Iodide Uptake and Thyroid Cancer—A Review

    Science.gov (United States)

    Gonçalves, Carlos F. L.; de Freitas, Mariana L.; Ferreira, Andrea C. F.

    2017-01-01

    Thyroid cancer is the most common malignant tumor of the endocrine system and the incidence has been increasing in recent years. In a great part of the differentiated carcinomas, thyrocytes are capable of uptaking iodide. In these cases, the main therapeutic approach includes thyroidectomy followed by ablative therapy with radioiodine. However, in part of the patients, the capacity to concentrate iodide is lost due to down-regulation of the sodium-iodide symporter (NIS), the protein responsible for transporting iodide into the thyrocytes. Thus, therapy with radioiodide becomes ineffective, limiting therapeutic options and reducing the life expectancy of the patient. Excessive ingestion of some flavonoids has been associated with thyroid dysfunction and goiter. Nevertheless, studies have shown that some flavonoids can be beneficial for thyroid cancer, by reducing cell proliferation and increasing cell death, besides increasing NIS mRNA levels and iodide uptake. Recent data show that the flavonoids apingenin and rutin are capable of increasing NIS function and expression in vivo. Herein we review literature data regarding the effect of flavonoids on thyroid cancer, besides the effect of these compounds on the expression and function of the sodium-iodide symporter. We will also discuss the possibility of using flavonoids as adjuvants for therapy of thyroid cancer. PMID:28604619

  16. Efficacy of flavonoids in the management of high blood pressure.

    Science.gov (United States)

    Clark, Jaime L; Zahradka, Peter; Taylor, Carla G

    2015-12-01

    Plant compounds such as flavonoids have been reported to exert beneficial effects in cardiovascular disease, including hypertension. Information on the effects of isolated individual flavonoids for management of high blood pressure, however, is more limited. This review is focused on the flavonoids, as isolated outside of the food matrix, from the 5 main subgroups consumed in the Western diet (flavones, flavonols, flavanones, flavan-3-ols, and anthocyanins), along with their effects on hypertension, including the potential mechanisms for regulating blood pressure. Flavonoids from all 5 subgroups have been shown to attenuate a rise in or to reduce blood pressure during several pathological conditions (hypertension, metabolic syndrome, and diabetes mellitus). Flavones, flavonols, flavanones, and flavanols were able to modulate blood pressure by restoring endothelial function, either directly, by affecting nitric oxide levels, or indirectly, through other pathways. Quercetin had the most consistent blood pressure-lowering effect in animal and human studies, irrespective of dose, duration, or disease status. However, further research on the safety and efficacy of the flavonoids is required before any of them can be used by humans, presumably in supplement form, at the doses required for therapeutic benefit. © The Author(s) 2015. Published by Oxford University Press on behalf of the International Life Sciences Institute. All rights reserved. For Permissions, please e-mail: journals.permissions@oup.com.

  17. Highly Oxygenated Flavonoids from the Leaves of Nicotiana plumbaginifolia (Solanaceae

    Directory of Open Access Journals (Sweden)

    Md. Shafiullah Shajib

    2017-11-01

    Full Text Available Nicotiana plumbaginifolia Viv. is an annual herb of the family Solanaceae, which grows abundantly in the weedy lands of Bangladesh . This plant possesses analgesic, antibacterial, anti-anxiety and hepatoprotective properties, and produces various phenolic compounds including flavonoids. The present study afforded determination of total phenolic and flavonoid contents, and for the first time, the isolation and characterization of highly oxygenated flavonoids, e.g., 3,3' ,5,6,7,8-hexamethoxy- 4',5'-methylenedioxyflavone (1, 3,3' ,4' ,5',5,6,7,8-octamethoxyflavone (2, exoticin, 6,7,4',5'-dimethylenedioxy-3,5,3'-trimethoxyflavone (3 and ( 3,3' ,4',5,5',8-hexamethoxy-6,7-methylenedioxyflavone (4 from the leaves of N. plumbaginifolia . All these flavonoids are rather rare natural products, and only found in a few genera, e.g.,Polygonum and Murraya. The structures of the isolated flavonoids were elucidated by comprehensive spectroscopic analyses, e.g., UV, 1H, 13C NMR, DEPT, HSQC, HMBC and MS.

  18. Regulation of Flavonoid Biosynthetic Genes in Germinating Arabidopsis Seedlings.

    Science.gov (United States)

    Kubasek, WL; Shirley, BW; McKillop, A; Goodman, HM; Briggs, W; Ausubel, FM

    1992-01-01

    Many higher plants, including Arabidopsis, transiently display purple anthocyanin pigments just after seed germination. We observed that steady state levels of mRNAs encoded by four flavonoid biosynthetic genes, PAL1 (encoding phenylalanine ammonia-lyase 1), CHS (encoding chalcone synthase), CHI (encoding chalcone isomerase), and DFR (encoding dihydroflavonol reductase), were temporally regulated, peaking in 3-day-old seedlings grown in continuous white light. Except for the case of PAL1 mRNA, mRNA levels for these flavonoid genes were very low in seedlings grown in darkness. Light induction studies using seedlings grown in darkness showed that PAL1 mRNA began to accumulate before CHS and CHI mRNAs, which, in turn, began to accumulate before DFR mRNA. This order of induction is the same as the order of the biosynthetic steps in flavonoid biosynthesis. Our results suggest that the flavonoid biosynthetic pathway is coordinately regulated by a developmental timing mechanism during germination. Blue light and UVB light induction experiments using red light- and dark-grown seedlings showed that the flavonoid biosynthetic genes are induced most effectively by UVB light and that blue light induction is mediated by a specific blue light receptor. PMID:12297632

  19. Antihypertensive properties of flavonoid-rich apple peel extract.

    Science.gov (United States)

    Balasuriya, Nileeka; Rupasinghe, H P Vasantha

    2012-12-15

    Hypertension is a major public health problem rising across the globe. Inhibition of angiotensin converting enzyme (ACE) is identified as a main therapeutic target in controlling high blood pressure. The present study investigated the ACE inhibitory property of a flavonoid-rich apple peel extract (FAE), its constituents, selected flavonoids and some quercetin metabolites using a biochemical assay of ACE inhibition and a human umbilical vein endothelial cell (HUVEC) model. FAE, all the tested flavonoids except genistein, and two quercetin metabolites (quercetin-3-O-glucuronic acid and quercetin-3-O-sulfate) significantly (p<0.05) inhibited ACE. Enzyme kinetic analysis revealed that flavonoids are competitive inhibitors of ACE. In the HUVEC model, FAE, quercetin-3-O-glucoside and quercetin-3-O-glucuronic acid inhibited significantly (p<0.05) ACE activity. Overall, FAE and most of the flavonoids tested showed ACE inhibition in vitro which needs further investigations using animal and human clinical trials. Copyright © 2012 Elsevier Ltd. All rights reserved.

  20. Distribution and biological activities of the flavonoid luteolin.

    Science.gov (United States)

    López-Lázaro, Miguel

    2009-01-01

    Epidemiological evidence suggests that flavonoids may play an important role in the decreased risk of chronic diseases associated with a diet rich in plant-derived foods. Flavonoids are also common constituents of plants used in traditional medicine to treat a wide range of diseases. The purpose of this article is to summarize the distribution and biological activities of one of the most common flavonoids: luteolin. This flavonoid and its glycosides are widely distributed in the plant kingdom; they are present in many plant families and have been identified in Bryophyta, Pteridophyta, Pinophyta and Magnoliophyta. Dietary sources of luteolin include, for instance, carrots, peppers, celery, olive oil, peppermint, thyme, rosemary and oregano. Preclinical studies have shown that this flavone possesses a variety of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial and anticancer activities. The ability of luteolin to inhibit angiogenesis, to induce apoptosis, to prevent carcinogenesis in animal models, to reduce tumor growth in vivo and to sensitize tumor cells to the cytotoxic effects of some anticancer drugs suggests that this flavonoid has cancer chemopreventive and chemotherapeutic potential. Modulation of ROS levels, inhibition of topoisomerases I and II, reduction of NF-kappaB and AP-1 activity, stabilization of p53, and inhibition of PI3K, STAT3, IGF1R and HER2 are possible mechanisms involved in the biological activities of luteolin.

  1. Flavonoids Inhibit the Respiratory Burst of Neutrophils in Mammals

    Directory of Open Access Journals (Sweden)

    Milan Ciz

    2012-01-01

    Full Text Available Neutrophils represent the front-line defence cells in protecting organisms against infection and play an irreplaceable role in the proper performance of the immune system. As early as within the first minutes of stimulation, neutrophilic NADPH oxidase is activated, and cells release large quantities of highly toxic reactive oxygen species (ROS. These oxidants can be highly toxic not only for infectious agents but also for neighboring host tissues. Since flavonoids exhibit antioxidant and anti-inflammatory effects, they are subjects of interest for pharmacological modulation of ROS production. The present paper summarizes contemporary knowledge on the effects of various flavonoids on the respiratory burst of mammalian neutrophils. It can be summarized that the inhibitory effects of flavonoids on the respiratory burst of phagocytes are mediated via inhibition of enzymes involved in cell signaling as well as via modulation of redox status. However, the effects of flavonoids are even more complex, and several sites of action, depending upon the flavonoid structure and way of application, are included.

  2. Different biosynthesis patterns among flavonoid 3-glycosides with distinct effects on accumulation of other flavonoid metabolites in pears (Pyrus bretschneideri Rehd..

    Directory of Open Access Journals (Sweden)

    Rui Zhai

    Full Text Available Flavonoid biosynthesis profile was clarified by fruit bagging and re-exposure treatments in the green Chinese pear 'Zaosu' (Pyrus bretschneideri Rehd. and its red mutant 'Red Zaosu'. Two distinct biosynthesis patterns of flavonoid 3-glycosides were found in 'Zaosu' pear. By comparison with 'Red Zaosu', the biosynthesis of flavonoid 3-galactosides and flavonoid 3-arabinosides were inhibited by bagging and these compounds only re-accumulated to a small degree in the fruit peel of 'Zaosu' after the bags were removed. In contrast, the biosynthesis of flavonoid 3-gluctosides and flavonoid 3-rutinosides was reduced by bagging and then increased when the fruits were re-exposed to sunlight. A combination of correlation, multicollinearity test and partial-correlation analyses among major flavonoid metabolites indicated that biosynthesis of each phenolic compound was independent in 'Zaosu' pear, except for the positive correlation between flavonoid 3-rutincosides and flavanols. In contrast with the green pear cultivar, almost all phenolic compounds in the red mutant had similar biosynthesis patterns except for arbutin. However, only the biosynthesis of flavonoid 3-galactosides was relatively independent and strongly affected the synthesis of the other phenolic compounds. Therefore, we propose a hypothesis that the strong accumulation of flavonoid 3-galactosides stimulated the biosynthesis of other flavonoid compounds in the red mutant and, therefore, caused systemic variation of flavonoid biosynthesis profiles between 'Zaosu' and its red mutant. This hypothesis had been further demonstrated by the enzyme activity of UFGT, and transcript levels of flavonoid biosynthetic genes and been well tested by a stepwise linear regression forecasting model. The gene that encodes flavonoid 3-galacosyltransferase was also identified and isolated from the pear genome.

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

    DEFF Research Database (Denmark)

    Lehka, Beata Joanna

    is a precursor for other commercially relevant flavonoids we developed a platform for the production of a library of flavonoid derivatives and screened them for antibacterial properties. Seven different yeast strains producing flavonoids (naringenin, kaempferol, dihydrokaempferol, apigenin and afzelechin...

  4. The influence of light quality on the accumulation of flavonoids in tobacco (Nicotiana tabacum L.) leaves.

    Science.gov (United States)

    Fu, Bo; Ji, Xiaoming; Zhao, Mingqin; He, Fan; Wang, Xiaoli; Wang, Yiding; Liu, Pengfei; Niu, Lu

    2016-09-01

    Flavonoids are important secondary metabolites in plants regulated by the environment. To analyze the effect of light quality on the accumulation of flavonoids, we performed a rapid analysis of flavonoids in extracts of tobacco leaves using UHPLC-QTOF. A total of 12 flavonoids were detected and identified in tobacco leaves, which were classified into flavonoid methyl derivatives and flavonoid glycoside derivatives according to the groups linked to the flavonoid core. Correlation analysis was further conducted to investigate the effect of different wavelengths of light on their accumulation. The content of flavonoid methyl derivatives was positively correlated with the proportions of far-red light (FR; 716-810nm) and near-infrared light (NIR; 810-2200nm) in the sunlight spectrum and negatively correlated with the proportion of ultraviolet (UV-A; 350-400nm) and the red/far-red ratio (R/FR). By contrast, the content of flavonoid glycoside derivatives was positively correlated with the proportion of UV-A and the R/FR, and negatively correlated with FR and NIR. The results indicated that light quality with higher proportions of FR and NIR increases the activity of flavonoid methyltransferases but suppresses the activity of flavonoid glycoside transferases. While a high proportion of UV-A and a high R/FR can increase flavonoid glycoside transferase activity but suppress flavonoid methyltransferase activity. Copyright © 2016 Elsevier B.V. All rights reserved.

  5. 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......, NMR spectroscopy and differential pH spectrophotometry. Quantification was performed on six of the eight conjugates based on calibration curves with the identical conjugates. There was no difference in the profile of the excreted conjugates according to treatment. The results demonstrated the more...... change in dose. The urinary excretion of ten dietary flavonoids was analysed after enzymatic hydrolysis by LC-MS and associated to the risk of ACS in a nested case-control study with 393 case-noncase pairs. The 393 case-noncase pairs were identified in the Danish Diet, Cancer and Health cohort comprising...

  6. Polycondensation Resins by Flavonoid Tannins Reaction with Amines

    Directory of Open Access Journals (Sweden)

    Francisco-Jose Santiago-Medina

    2017-01-01

    Full Text Available Reaction of a condensed flavonoid tannin, namely mimosa tannin extract with a hexamethylene diamine, has been investigated. For that purpose, catechin was also used as a flavonoid model compound and treated in similar conditions. Solid-state cross-polarisation/magic-angle spinning (CP-MAS carbon 13 nuclear magnetic resonance (13C NMR and matrix assisted laser desorption ionisation time of flight (MALDI-ToF mass spectroscopy studies revealed that polycondensation compounds leading to resins were obtained by the reaction of the amines with the phenolic hydroxy groups of the tannin. Simultaneously, a second reaction leading to the formation of ionic bonds between the two groups occurred. These new reactions have been shown to clearly lead to the reaction of several phenolic hydroxyl groups, and flavonoid unit oligomerisation, to form hardened resins.

  7. Buckwheat seedling flavonoids do not undergo rapid turnover

    International Nuclear Information System (INIS)

    Margna, U.; Vainjaerv, T.

    1981-01-01

    Pulse-labelling with exogenous [1- 14 C]-L-phenylalanine showed that of all flavonoids of buckwheat seedling cotyledons only anthocyanins underwent a slow turnover (not more than 6-8 per cent a day) whilst the major flavonoids, rutin and four C-glycosylflavones, remained metabolically stable within at least 7 days. From excised hypocotyls pulse-labelled flavonoids (anthocyanins and rutin) began to disappear gradually beginning with the second day of incubation. As hypocotyls, however, during prolonged incubation soon began to autolyse a considerable part of that loss was obviously due to abnormal shifts in cell metabolic activities with a possibility that some microbial process was also involved. In hypocotyls of intact seedlings pulse-labelled rutin, similar to rutin in cotyledons, showed no signs of turnover. (author)

  8. Diamond-like nanoparticles influence on flavonoids transport: molecular modelling

    Science.gov (United States)

    Plastun, Inna L.; Agandeeva, Ksenia E.; Bokarev, Andrey N.; Zenkin, Nikita S.

    2017-03-01

    Intermolecular interaction of diamond-like nanoparticles and flavonoids is investigated by numerical simulation. Using molecular modelling by the density functional theory method, we analyze hydrogen bonds formation and their influence on IR - spectra and structure of molecular complex which is formed due to interaction between flavonoids and nanodiamonds surrounded with carboxylic groups. Enriched adamantane (1,3,5,7 - adamantanetetracarboxylic acid) is used as an example of diamond-like nanoparticles. Intermolecular forces and structure of hydrogen bonds are investigated. IR - spectra and structure parameters of quercetin - adamantanetetracarboxylic acid molecular complex are obtained by numerical simulation using the Gaussian software complex. Received data coincide well with experimental results. Intermolecular interactions and hydrogen bonding structure in the obtained molecular complex are examined. Possibilities of flavonoids interaction with DNA at the molecular level are also considered.

  9. Phyto chemical study of the flavonoids of khaya senegalensis

    International Nuclear Information System (INIS)

    Shakir, S. H.

    2005-03-01

    Phyto chemical screening of the leaves of Khaya senegalensis revealed the presence of flavonoids. Crushed air-dried leaves of Khaya senegalensis were extracted at ambient temperature with ethanol. The crude product obtained after removal of the solvent was subjected to chromatographic fractionation. Using silica gel and the solvent system: butanol: acetic acid: water (3:1:6 ; V:V:V) a pure flavonoid was isolated. The colour reactions and the UV spectra of the isolated flavonoid clearly indicated that it is a flavone. The hydroxylation pattern of the isolated flavone was studies using shift reagents. The structural features were further elucidated via IR, NMR and Mass spectrophotometry. The following tentative structure was proposed.(Author)

  10. Leishmanicidal Activity of Nine Novel Flavonoids from Delphinium staphisagria

    Directory of Open Access Journals (Sweden)

    Inmaculada Ramírez-Macías

    2012-01-01

    Full Text Available Objectives. To evaluate the in vitro leishmanicidal activity of nine flavonoid derivatives from Delphinium staphisagria against L. infantum and L. braziliensis. Design and Methods. The in vitro activity of compounds 1–9 was assayed on extracellular promastigote and axenic amastigote forms and on intracellular amastigote forms of the parasites. Infectivity and cytotoxicity tests were carried on J774.2 macrophage cells using Glucantime as the reference drug. The mechanisms of action were analysed performing metabolite excretion and transmission electronic microscope ultrastructural alteration studies. Results. Nine flavonoids showed leishmanicidal activity against promastigote as well as amastigote forms of Leishmania infantum and L. braziliensis. These compounds were nontoxic to mammalian cells and were effective at similar concentrations up to or lower than that of the reference drug (Glucantime. The results showed that 2″-acetylpetiolaroside (compound 8 was clearly the most active. Conclusion. This study has demonstrated that flavonoid derivatives are active against L. infantum and L. braziliensis.

  11. Flavonoid rutin increases thyroid iodide uptake in rats.

    Directory of Open Access Journals (Sweden)

    Carlos Frederico Lima Gonçalves

    Full Text Available Thyroid iodide uptake through the sodium-iodide symporter (NIS is not only an essential step for thyroid hormones biosynthesis, but also fundamental for the diagnosis and treatment of different thyroid diseases. However, part of patients with thyroid cancer is refractory to radioiodine therapy, due to reduced ability to uptake iodide, which greatly reduces the chances of survival. Therefore, compounds able to increase thyroid iodide uptake are of great interest. It has been shown that some flavonoids are able to increase iodide uptake and NIS expression in vitro, however, data in vivo are lacking. Flavonoids are polyhydroxyphenolic compounds, found in vegetables present in human diet, and have been shown not only to modulate NIS, but also thyroperoxidase (TPO, the key enzyme in thyroid hormones biosynthesis, besides having antiproliferative effect in thyroid cancer cell lines. Therefore, we aimed to evaluate the effect of some flavonoids on thyroid iodide uptake in Wistar rats in vivo. Among the flavonoids tested, rutin was the only one able to increase thyroid iodide uptake, so we decided to evaluate the effect of this flavonoid on some aspects of thyroid hormones synthesis and metabolism. Rutin led to a slight reduction of serum T4 and T3 without changes in serum thyrotropin (TSH, and significantly increased hypothalamic, pituitary and brown adipose tissue type 2 deiodinase and decreased liver type 1 deiodinase activities. Moreover, rutin treatment increased thyroid iodide uptake probably due to the increment of NIS expression, which might be secondary to increased response to TSH, since TSH receptor expression was increased. Thus, rutin might be useful as an adjuvant in radioiodine therapy, since this flavonoid increased thyroid iodide uptake without greatly affecting thyroid function.

  12. Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae)

    International Nuclear Information System (INIS)

    Pereira, Cristiane; Barreto Junior, Cleber Bomfim; Kuster, Ricardo Machado; Simas, Naomi Kato; Sakuragui, Cassia Monica; Porzel, Andrea; Wessjohann, Ludger

    2012-01-01

    This work describes the phytochemical study of the methanol extract obtained from leaves of Guarea macrophylla, leading to the isolation and identification of three flavonoid glycosides (quercetin 3-O-β-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-β-D-glucopyranoside) and a neolignan glucoside, dehydrodiconiferyl alcohol-4-b-D-glucoside. All compounds were identified by a combination of spectroscopic methods ( 1 H, 1D, 2D NMR, 13 C and UV), ESI-MS and comparison with the literature data. This is the first report of flavonoids in the genus Guarea and of a neolignan glucoside in the Meliaceae family. (author)

  13. Primula latifolia Lapeyr. and Primula vulgaris Hudson flavonoids.

    Science.gov (United States)

    Colombo, Paola S; Flamini, Guido; Fico, Gelsomina

    2014-01-01

    Three flavonoids were isolated from the leaf MeOH extracts of Primula latifolia Lapeyr. and Primula vulgaris Hudson collected from Italian Alps: rutin (1) and kaempferol 3-neohesperidoside (2) from P. latifolia, and kaempferol 3-β-O-glucopyranosyl-(1 → 2) gentiobioside (3) from P. vulgaris. The structures were assigned on the basis of their (1)H and (13)C NMR data, including those derived from 2D NMR, as well as on HPLC-MS results. This article is the first to report on P. vulgaris tissue flavonoids after Harborne's study in 1968 and the first work ever on these compounds from P. latifolia.

  14. Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae

    Directory of Open Access Journals (Sweden)

    Cristiane Pereira

    2012-01-01

    Full Text Available This work describes the phytochemical study of the methanol extract obtained from leaves of Guarea macrophylla, leading to the isolation and identification of three flavonoid glycosides (quercetin 3-O-β-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-β-D-glucopyranoside and a neolignan glucoside, dehydrodiconiferyl alcohol-4-β-D-glucoside. All compounds were identified by a combination of spectroscopic methods (¹H, 1D, 2D NMR, 13C and UV, ESI-MS and comparison with the literature data. This is the first report of flavonoids in the genus Guarea and of a neolignan glucoside in the Meliaceae family.

  15. Effect of flavonoids on the metabolism of xenobiotics

    OpenAIRE

    Smetanová, Anna

    2009-01-01

    Charles University in Prague Faculty of Pharmacy in Hradec Králové Department of Biochemical Sciences Title, Name, Surname of candidate: Mgr. Anna Smetanová Title, Name, Surname of tutor: Doc. Ing. Barbora Szotáková, Ph.D. Title of a rigorous work: The influence of flavonoids on the metabolism of xenobiotics Flavonoids are wide spread plant secondary metabolites with the protective effect against the cancer. One of the protective mechanisms of action is the modulation of the biotransformation...

  16. Effects of dietary flavonoids intake in Saudi patients with coronary heart disease

    Directory of Open Access Journals (Sweden)

    Mohammed A Alsaif

    2007-01-01

    Conclusions: The findings of the study support a potential protective effect of dietary flavonoids in relation to CHD. The study showed that consuming more Flavonoids may have positive effect on lowering blood lipids.

  17. Total flavonoid concentrations of bryophytes from Tianmu Mountain, Zhejiang Province (China): Phylogeny and ecological factors

    OpenAIRE

    Wang, Xin; Cao, Jianguo; Dai, Xiling; Xiao, Jianbo; Wu, Yuhuan; Wang, Quanxi

    2017-01-01

    The flavonoids in bryophytes may have great significance in phylogeny and metabolism research. However, to date there has been little research on bryophyte metabolites, especially flavonoids. To redress this somewhat, we determined flavonoid concentrations of bryophytes from Tianmu Mountain through a colorimetric assay and considered the factors influencing the results. This is the first time that the flavonoid contents of bryophytes have been examined in detail. The results revealed a range ...

  18. Spectrophotometric determination of the total flavonoid content in Ocimum basilicum L. (Lamiaceae) leaves.

    Science.gov (United States)

    da Silva, Layzon Antonio Lemos; Pezzini, Bianca Ramos; Soares, Luciano

    2015-01-01

    The chemical characterization is essential to validate the pharmaceutical use of vegetable raw materials. Ultraviolet spectroscopy is an important technique to determine flavonoids, which are important active compounds from Ocimum basilicum. The objective of this work was to optimize a spectrophotometric method, based on flavonoid-aluminum chloride (AlCl3) complexation to determine the total flavonoid content (TFC) in leaves of O. basilicum (herbal material), using response surface methodology. The effects of (1) the herbal material: Solvent ratio (0.02, 0.03, 0.05, 0.07, and 0.08 g/mL), (2) stock solution volume (0.8, 2.3, 4.4, 6.5, and 8.0 mL) and (3) AlCl3 volume (0.8, 1.0, 1.2, 1.4, and 1.6 mL) on the TFC were evaluated. The analytical performance parameters precision, linearity and robustness of the method were tested. The herbal material: Solvent ratio and stock solution volume showed an important influence on the method response. After choosing the optimized conditions, the method exhibited a precision (RSD%) lower than 6% for repeatability (RSD%) and lower than 8% for intermediate precision (on the order of literature values for biotechnological methods), coefficient of correlation of 0.9984, and no important influence could be observed for variations of the time of complexation with AlCl3. However, the time and temperature of extraction were critical for TFC method and must be carefully controlled during the analysis. Thus, this study allowed the optimization of a simple, fast and precise method for the determination of the TFC in leaves of O. basilicum, which can be used to support the quality assessment of this herbal material.

  19. Spectrophotometric determination of the total flavonoid content in Ocimum basilicum L. (Lamiaceae) leaves

    Science.gov (United States)

    da Silva, Layzon Antonio Lemos; Pezzini, Bianca Ramos; Soares, Luciano

    2015-01-01

    Background: The chemical characterization is essential to validate the pharmaceutical use of vegetable raw materials. Ultraviolet spectroscopy is an important technique to determine flavonoids, which are important active compounds from Ocimum basilicum. Objective: The objective of this work was to optimize a spectrophotometric method, based on flavonoid-aluminum chloride (AlCl3) complexation to determine the total flavonoid content (TFC) in leaves of O. basilicum (herbal material), using response surface methodology. Materials and Methods: The effects of (1) the herbal material: Solvent ratio (0.02, 0.03, 0.05, 0.07, and 0.08 g/mL), (2) stock solution volume (0.8, 2.3, 4.4, 6.5, and 8.0 mL) and (3) AlCl3 volume (0.8, 1.0, 1.2, 1.4, and 1.6 mL) on the TFC were evaluated. The analytical performance parameters precision, linearity and robustness of the method were tested. Results: The herbal material: Solvent ratio and stock solution volume showed an important influence on the method response. After choosing the optimized conditions, the method exhibited a precision (RSD%) lower than 6% for repeatability (RSD%) and lower than 8% for intermediate precision (on the order of literature values for biotechnological methods), coefficient of correlation of 0.9984, and no important influence could be observed for variations of the time of complexation with AlCl3. However, the time and temperature of extraction were critical for TFC method and must be carefully controlled during the analysis. Conclusion: Thus, this study allowed the optimization of a simple, fast and precise method for the determination of the TFC in leaves of O. basilicum, which can be used to support the quality assessment of this herbal material. PMID:25709217

  20. Inverse association of tea and flavonoid intakes with incident myocardial infarction : the Rotterdam Study

    NARCIS (Netherlands)

    Geleijnse, J.M.; Launer, L.J.; Kuip, van der D.A.M.; Hofman, A.; Witteman, J.C.M.

    2002-01-01

    Background: Dietary flavonoids may protect against cardiovascular disease, but evidence is still conflicting. Tea is the major source of flavonoids in Western populations. Objective: The association of tea and flavonoid intake with incident myocardial infarction was examined in the general Dutch

  1. De novo production of the flavonoid naringenin in engineered Saccharomyces cerevisiae

    NARCIS (Netherlands)

    Koopman, F.W.; Beekwilder, J.; Crimi, B.; Van Houwelingen, A.; Hall, R.D.; Bosch, D.; Van Maris, A.J.A.; Pronk, J.T.; Daran, J.M.

    2012-01-01

    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

  2. Flavonoid values for USDA survey foods and beverages 2007-2010

    Science.gov (United States)

    Comprehensive databases of the flavonoid content of foods are needed to more accurately estimate dietary intakes of these compounds. The Flavonoid Values for Survey Foods and Beverages 2007-2010 allows estimation of flavonoid intakes based on all foods and beverages reported in the national survey,...

  3. Total flavonoid concentrations of bryophytes from Tianmu Mountain, Zhejiang Province (China): Phylogeny and ecological factors.

    Science.gov (United States)

    Wang, Xin; Cao, Jianguo; Dai, Xiling; Xiao, Jianbo; Wu, Yuhuan; Wang, Quanxi

    2017-01-01

    The flavonoids in bryophytes may have great significance in phylogeny and metabolism research. However, to date there has been little research on bryophyte metabolites, especially flavonoids. To redress this somewhat, we determined flavonoid concentrations of bryophytes from Tianmu Mountain through a colorimetric assay and considered the factors influencing the results. This is the first time that the flavonoid contents of bryophytes have been examined in detail. The results revealed a range of total flavonoid concentrations in 90 samples collected from Tianmu Mountain from 1.8 to 22.3 mg/g (w/w). The total flavonoid contents of liverworts were generally higher than those of mosses; acrocarpous mosses had generally higher values than that of pleurocarpous mosses. The total flavonoid contents of bryophytes growing at lower light levels were general higher than those growing in full-sun. The total flavonoid contents of epiphytic bryophytes were highest, while those of aquatic bryophytes were the lowest. Total flavonoid contents of species growing at low-latitudes were much higher than those at high-latitude individuals. In conclusion, total flavonoid contents of bryophytes have some connection with plant phylogeny; more flavonoids might be contained in relatively primitive bryophytes. Meanwhile, the effects of ecological factors on total flavonoid contents of bryophytes exist; light and habitat (especially tree habitat and river habitat) might be representative factor.

  4. Total flavonoid concentrations of bryophytes from Tianmu Mountain, Zhejiang Province (China: Phylogeny and ecological factors.

    Directory of Open Access Journals (Sweden)

    Xin Wang

    Full Text Available The flavonoids in bryophytes may have great significance in phylogeny and metabolism research. However, to date there has been little research on bryophyte metabolites, especially flavonoids. To redress this somewhat, we determined flavonoid concentrations of bryophytes from Tianmu Mountain through a colorimetric assay and considered the factors influencing the results. This is the first time that the flavonoid contents of bryophytes have been examined in detail. The results revealed a range of total flavonoid concentrations in 90 samples collected from Tianmu Mountain from 1.8 to 22.3 mg/g (w/w. The total flavonoid contents of liverworts were generally higher than those of mosses; acrocarpous mosses had generally higher values than that of pleurocarpous mosses. The total flavonoid contents of bryophytes growing at lower light levels were general higher than those growing in full-sun. The total flavonoid contents of epiphytic bryophytes were highest, while those of aquatic bryophytes were the lowest. Total flavonoid contents of species growing at low-latitudes were much higher than those at high-latitude individuals. In conclusion, total flavonoid contents of bryophytes have some connection with plant phylogeny; more flavonoids might be contained in relatively primitive bryophytes. Meanwhile, the effects of ecological factors on total flavonoid contents of bryophytes exist; light and habitat (especially tree habitat and river habitat might be representative factor.

  5. Effect of a Long Term Treatment by Algerian Propolis Flavonoids on ...

    African Journals Online (AJOL)

    Our study carried out in vivo, using liver mitochondria isolated from albinos rats, treats the effect of a long term treatment by Algerian propolis ethanolic extract and their flavonic aglycones and glycosides to the amount of 100 mg/kg on mitochondrial antioxidant-prooxidant balance. Our results showed that all extracts ...

  6. Total phenols, flavonoids, anthocyanins, ascorbic acid contents and ...

    African Journals Online (AJOL)

    mmpa

    2014-03-05

    Mar 5, 2014 ... The antioxidant capability, total phenol, total flavonoid, anthocyanins, ascorbic acid contents, and reducing power contents of polar and non-polar extracts for flower and leaves in two stages of growth for Rhamnus kurdica Boiss in flowering were evaluated in this work. The polar extraction of flower of R.

  7. Inhibition effect of flavonoid extract of Euphorbia guyoniana on the ...

    African Journals Online (AJOL)

    The influence of flavonoids extracts of three parts of Euphorbia Guyoniana towards the corrosion of type API 5L X52 steel in 15% H2SO4 has been evaluated by weight loss method and polarization technique. The results showed that extracts are a good inhibitors for API 5L X52 steel in this medium. The corrosion inhibition ...

  8. Flavonoid insertion into cell walls improves wood properties.

    Science.gov (United States)

    Ermeydan, Mahmut A; Cabane, Etienne; Masic, Admir; Koetz, Joachim; Burgert, Ingo

    2012-11-01

    Wood has an excellent mechanical performance, but wider utilization of this renewable resource as an engineering material is limited by unfavorable properties such as low dimensional stability upon moisture changes and a low durability. However, some wood species are known to produce a wood of higher quality by inserting mainly phenolic substances in the already formed cell walls--a process so-called heartwood formation. In the present study, we used the heartwood formation in black locust (Robinia pseudoacacia) as a source of bioinspiration and transferred principles of the modification in order to improve spruce wood properties (Picea abies) by a chemical treatment with commercially available flavonoids. We were able to effectively insert hydrophobic flavonoids in the cell wall after a tosylation treatment for activation. The chemical treatment reduced the water uptake of the wood cell walls and increased the dimensional stability of the bulk spruce wood. Further analysis of the chemical interaction of the flavonoid with the structural cell wall components revealed the basic principle of this bioinspired modification. Contrary to established modification treatments, which mainly address the hydroxyl groups of the carbohydrates with hydrophilic substances, the hydrophobic flavonoids are effective by a physical bulking in the cell wall most probably stabilized by π-π interactions. A biomimetic transfer of the underlying principle may lead to alternative cell wall modification procedures and improve the performance of wood as an engineering material.

  9. Role of dietary flavonoids in amelioration of sugar induced cataractogenesis.

    Science.gov (United States)

    Patil, Kapil K; Meshram, Rohan J; Dhole, Nagesh A; Gacche, Rajesh N

    2016-03-01

    Sugar induced cataractogenesis and visual impairment is more prominent ophthalmic problem in humans suffering from diabetes. Flavonoids have been identified as one of the therapeutically important class of phytochemicals possessing myriad of biological activities. Analyzing the anti-cataract effects of flavonoids from natural sources is an important aspect owing to their bioavailability in variety of dietary sources. In the present study a panel of ten dietary flavonoids like 3, 6-dihydroxy flavone, 3, 7-dihydroxy flavone, chrysin, 3-hydroxy-7-methoxy flavone, apigenin, genistein, baicalein, galangin, Biochanin-A, and diosmin were evaluated for their anti-cataract effects in sugar induced lens model studies. Series of parameters like role of flavonoids in glycation induced lens opacity, protein aggregation measurements, carbonyl group formation: a biochemical marker of glycation reaction, non-tryptophan fluorescence: a marker of formation of advanced glycation end products (AGEs) and assessment of (experimental and in silico) aldose reductase inhibition: a key enzyme of polyol pathway involved in cataractogenesis. The results of the study clearly demonstrated the impressive anti-cataract activity of chrysin followed by significant activity by apigenin, baicalein and genistein. The results of the present study may find applications in formulation of functional foods and neutraceuticals for the management of diabetic cataract. Copyright © 2016 Elsevier Inc. All rights reserved.

  10. Optimal process for the extraction and identification of flavonoids ...

    African Journals Online (AJOL)

    The study has been carried out to investigate the effects of single factors such as temperature, extraction time, concentration of ethanol, material ratio and no. of extractions on the contents of flavonoids present in the leaves of Polyalthia longifolia. On this basis, an L16 orthogonal design of experiment was used to determine ...

  11. Comparative antioxidant activity, total phenol and total flavonoid ...

    African Journals Online (AJOL)

    Antioxidants are compounds which act as a major defense against oxidative stress caused by free radicals. In this study, a comparative evaluation of the antioxidant properties, phenolic and flavonoid contents of the methanolic extracts of Ocimum gratissimum Linn and Ocimum canum Sims was carried out. Crude extracts of ...

  12. Antioxidant activity, phenolic and flavonoid content in leaves, flowers ...

    African Journals Online (AJOL)

    The nutraceutical composition (phenolics and flavonoids) of all leaves, flowers, stems and seeds of mallow, Malva sylvestris L., as well as their antioxidant properties were studied using in vitro methods: ferric reducing antioxidant power (FRAP) assay, by scavenging of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and total ...

  13. Effect of Processing on the Antioxidants (Vitamin C and Flavonoids ...

    African Journals Online (AJOL)

    The effect of different processing methods: fresh milling (FRM), sun drying (SND), oven drying (OVD), steaming (STM) and a combination of these methods on the vitamin C and flavonoids constituents of selected leafy vegetables Vernonia amygdalina, Gnetum africana, Gongronema latifolium and Ocimum gratissimum was ...

  14. Ultrasonic-Assisted Extraction and Antioxidant Activity of Flavonoids ...

    African Journals Online (AJOL)

    Results: The main flavonoid in Adinandra nitida leaf was identified as camellianin A. Optimal extraction .... equation with the Design Expert software. (version 8.0, State-Ease, Inc, Statistics Made. Easy, Minneapolis, MN). The quadratic polynomial equation is shown in Eq 2. ... polynomial stepwise equations shown in Eqs 3 -.

  15. Flavonoids Affect Host-Microbiota Crosstalk through TLR Modulation

    Directory of Open Access Journals (Sweden)

    Francisco J. Pérez-Cano

    2014-10-01

    Full Text Available Interaction between host cells and microbes is known as crosstalk. Among other mechanisms, this takes place when certain molecules of the micro-organisms are recognized by the toll-like receptors (TLRs in the body cells, mainly in the intestinal epithelial cells and in the immune cells. TLRs belong to the pattern-recognition receptors and represent the first line of defense against pathogens, playing a pivotal role in both innate and adaptive immunity. Dysregulation in the activity of such receptors can lead to the development of chronic and severe inflammation as well as immunological disorders. Among components present in the diet, flavonoids have been suggested as antioxidant dietary factors able to modulate TLR-mediated signaling pathways. This review focuses on the molecular targets involved in the modulatory action of flavonoids on TLR-mediated signaling pathways, providing an overview of the mechanisms involved in such action. Particular flavonoids have been able to modify the composition of the microbiota, to modulate TLR gene and protein expression, and to regulate the downstream signaling molecules involved in the TLR pathway. These synergistic mechanisms suggest the role of some flavonoids in the preventive effect on certain chronic diseases.

  16. Quantification of total phenolic and flavonoid contents in Cassia ...

    African Journals Online (AJOL)

    The aim of this work was to quantify the total phenolic (TPC) and flavonoid contents (TFC) of Cassia tora and laptadeniahastata vegetables consumed in Kano state, Nigeria. Presence of TPC in the leaves of cassia tora and Laptadiniahastata from different sampling areas are as follows: Bebeji sample had 4.41±0.02 mg/g ...

  17. Main flavonoids in needles of Larix decidu A

    NARCIS (Netherlands)

    Niemann, Gerard J.

    Present work. Freeze-dried needles were extracted with acetone-water. Ether and butanol fractions were separated by repeated banding on paper. Nine major flavonoids were isolated (in solution) and identified by chromatographic and UV spectral data of both the original and alkaline and/or acid

  18. Kaempferol, a flavonoid compound from Gynura medica induced ...

    African Journals Online (AJOL)

    Background: Kaempferol, a natural flavonoid, has been shown to induce cancer cell apoptosis and cell growth inhibition in several tumors. Previously we have conducted a full investigation on the chemical constituents of Gynura medica, kaempferol and its glycosides are the major constituents of G. medica. Here we ...

  19. Antioxidant activity, total phenolic and flavonoid contents of the ...

    African Journals Online (AJOL)

    Elytraria marginata (Vahl) isused in Nigeria folk medicine as febrifuges, pulmonary problems and cancer related ailments. This study evaluated scientifically the phytochemical screening, antioxidant, total phenolic and flavonoids contents of the whole plant extract with a view to validate its folkloric usage. The phytochemical ...

  20. Antioxidant activity, phenolic and flavonoid contents of some wild ...

    African Journals Online (AJOL)

    This study reported on five plants known for their use in traditional medicine in southeastern Algeria, namely: Artemisia campestris, Asteriscus pygmaeus, Pituranthos chlorantus, Pallenis spinosa and Aizoon hispanicum. The work aimed to determine the antioxidant activity, phenol and flavonoid contents of their aqueous ...

  1. [AUXINS AND CYTOKININES SYNTHESIS BY BRADYRHIZOBIUM JAPONICUM UNDER FLAVONOIDS INFLUENCE].

    Science.gov (United States)

    Leonova, N O

    2015-01-01

    Research the ability of different by effectiveness symbiotic nitrogen-fixing soybean bacteria Bradyrhizobium japonicum to the synthesis of phytohormones-stimulators auxins and cytokinins for the actions of plant flavonoids genistein and naringenin. Extracellular phytohormonal compound isolated from the supernatant culture liquid of the soybean rhizobia by redistribution of phytohormones in two phases solvent immiscible with each other. Auxins and cytokinins were determined by thin layer spectra densitometry chromatography. Shown the ability of symbiotic diastrophic soybean strains to synthesize auxins (4-1067 mg/g of absolutely dry biomass) and cytokinins (141-1554 mg/g of absolutely dry biomass). Cultivation soybean rhizobia in the presence of flavonoid compounds genistein and naringenin leads to the narrowing of the range and reducing the number of phytohormones: unchecked synthesis of indole-3-carboxylic acid, indole-3-carbinol, indole-3-acetic acid hydrazide and zeatin. Depressing effect of flavonoids on the phytohormones in soybean rhizobia synthesis is probably due to changes in metabolism microsymbiotic bacteria that are not aimed at the synthesis of secondary metabolites and to launch effective nodulating mechanisms, and also the concentration of flavonoid compounds in the nutrient medium.

  2. Microbial production of the flavonoids garbanzol, resokaempferol and fisetin

    DEFF Research Database (Denmark)

    2016-01-01

    The invention provides a genetically modified micro-organism comprising one or more transgene for the production of one or more of the flavonoids garbanzol, resokaempferol and fisetin. The micro-organism may be a bacterial or yeast cell engineered to express a metabolic pathway for garbanzol...

  3. Antioxidant activity and total phenolic and flavonoid content of ...

    African Journals Online (AJOL)

    ajl yemi

    2011-12-19

    Dec 19, 2011 ... Full Length Research Paper. Antioxidant activity and total phenolic and flavonoid content of Astragalus squarrosus Bunge. Jinous Asgarpanah1*, Saeed Mohammadi Motamed2, Avishan Farzaneh1, Bahareh. Ghanizadeh1 and Simin Tomraee2. 1Young Researchers Club (YRC), Pharmaceutical Sciences ...

  4. Ultrasonic extraction of flavonoids and phenolics from loquat ...

    African Journals Online (AJOL)

    Ethanol was used to extract flavonoids and phenolics from loquat (Eriobotrya japonica Lindl. cv. Ruantiaobaisha) flowers with ultrasonic pharmaceutical managing machine. Single-factor and orthogonal experiment were used to investigate the optimum extraction condition. The results showed that, the combination of 30°C, ...

  5. Flavonoids inhibit the respiratory burst of neutrophils in mammals

    Czech Academy of Sciences Publication Activity Database

    Číž, Milan; Denev, P.; Kratchanova, M.; Vašíček, Ondřej; Ambrožová, Gabriela; Lojek, Antonín

    2012-01-01

    Roč. 2012, č. 2012 (2012), ID 181295 ISSN 1942-0900 R&D Projects: GA ČR(CZ) GA524/08/1753 Institutional research plan: CEZ:AV0Z50040702 Keywords : flavonoids * neutrophils * respiratory burst Subject RIV: BO - Biophysics Impact factor: 3.393, year: 2012

  6. Health benefits of orange juice and citrus flavonoids

    Science.gov (United States)

    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...

  7. Antioxidant and Anti-Fatigue Activities of Flavonoids from Puerariae ...

    African Journals Online (AJOL)

    This study evaluated the antioxidant and anti-fatigue activities of flavonoids from Puerariae radix (FPR). In vitro antioxidant activities of FPR were investigated through hydroxyl and superoxide radical scavenging activities. In vivo anti-fatigue activity of FPR was investigated through loaded swimming exercise of mice. Results ...

  8. Antioxidant activity and total phenolic and flavonoid content of ...

    African Journals Online (AJOL)

    ajl yemi

    2011-12-19

    Dec 19, 2011 ... purposes. Medicinal values of these compounds are well ... The present report describes the total phenolics and flavonoids .... an electron donated by an antioxidant compound, the. DPPH is decolorized, which can be quantitatively mea- sured from the changes in absorbance. The IC50 value of the extract ...

  9. Flavonoids as Chemopreventive and Therapeutic Agents Against Lung Cancer

    Directory of Open Access Journals (Sweden)

    Albert Cabrera

    2014-05-01

    Full Text Available The objective of the present review is to study the relationship between flavonoids and lung cancer, proposing that their regular consumption in Western diets could be beneficial for protecting patients against lung cancer. An extensive search of the scientific literature was performed in the following electronic specialized databases (PubMed central (PMC-NBCI, Elsevier Journal, SciELO Spain, Scirus, Science Direct, including studies in animals, cells, and humans, in order to establish the effect of flavonoids in the prevention and development of lung cancer. Although in vitro and animal studies show the potential ability of flavonoids to act against different types of cancers, especially against lung cancers, the diverse results reported within epidemiological studies, together with the lack of experiments in humans, are the major factors in limiting making dietary recommendations based on scientific evidence for the management of patients with lung cancer. Therefore, the authors of the present study recommend following the dietary health practice guidelines which promotes the consumption of food enriched in flavonoids and reflects the current state of knowledge of an effective and appropriate diet in lung cancer patients.Erratum in: Rev Esp Nutr Hum Diet. 2013;17(2:91-92Link: http://www.renhyd.org/index.php/renhyd/article/view/6/17

  10. Antioxidant activity and total phenolic and flavonoid content of ...

    African Journals Online (AJOL)

    The antioxidant capacity of the flowering aerial parts of Astragalus squarrosus was determined by 1,1- diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and ferric thiocyanate methods. The phenolic and flavonoid content was also measured. A. squarrosus showed weak free radical scavenging activity with the DPPH ...

  11. Investigation Of Total Phenolic, Total Flavonoid, Antioxidantand Allyl ...

    African Journals Online (AJOL)

    Background: This study was carried out to investigate the total polyphenol (TP), total flavonoid (TF), antioxidative effect and allyl isothyocyanate (ITC) content in different organs of wasabi plant grown in an organic system. Materials and Methods: Invitro study of methanol and boiled water extracts of wasabi were conducted ...

  12. Flavonoids as Nutraceuticals: A Review | Tapas | Tropical Journal of ...

    African Journals Online (AJOL)

    Due to the variety of pharmacological activities in the mammalian body, flavonoids are more correctly referred as “nutraceuticals”. Keywords: Bioflavonoids, Structure-Classification, Nutraceuticals, Antimicrobial activities, Anti-oxidant activity, Metabolic effects. Tropical Journal of Pharmaceutical Research Vol. 7 (3) 2008: pp.

  13. Quantification of alkaloids, phenols and flavonoids in sunflower ...

    African Journals Online (AJOL)

    Allelochemicals in leaves, stems and roots of sunflower (cv Hysun 38) were determined using thin layer chromatography (TLC) for alkaloids and spectrophotometry for phenols and flavonoids. In the TLC, the highest Rf value was recorded in leaves, followed by roots and stems, a sequence that held true also for the quantity ...

  14. Quantification and antibacterial activity of flavonoids in coffee samples

    African Journals Online (AJOL)

    Methodology: In the current study quantity of flavonoids and antibacterial activities were determined in different coffee samples namely Nescafe classic, Nescafe gold, Nescafe martina, original, creamy and cafe soluvel by using standard methodology available in literature. Results: Nescafe original and gold showed highest ...

  15. Isolation of flavonoids from mulberry (Morus alba L.) leaves with ...

    African Journals Online (AJOL)

    STORAGESEVER

    2008-07-04

    Jul 4, 2008 ... notable biological activities. Nowadays, the traditional separation methods about the flavonoids of mulberry leaves used so far were limited to simple techniques such as extraction and precipitation leading to low recoveries. Hence a more efficient and simple purification method for TFs in mulberry leaves is.

  16. Quercetin: A Versatile Flavonoid | Lakhanpal | Internet Journal of ...

    African Journals Online (AJOL)

    Flavonoids occur naturally in fruits, vegetables and beverages such as tea and wine. Quercetin is the major ... Quercetin provides many health promoting benefits, including improvement of cardiovascular health, eye diseases, allergic disorders, arthritis, reducing risk for cancers and many more. The main aim of this review ...

  17. The effect of flavonoid derivatives on doxorubicin transport and metabolism

    Czech Academy of Sciences Publication Activity Database

    Václavíková, R.; Kondrová, E.; Ehrlichová, Marie; Boumendjel, A.; Kovář, Jan; Stopka, Pavel; Souček, P.; Gut, I.

    2008-01-01

    Roč. 16, č. 4 (2008), s. 2034-2042 ISSN 0968-0896 Institutional research plan: CEZ:AV0Z40320502; CEZ:AV0Z50520514 Keywords : Doxorubicin * Quercetin * Flavonoids * P-Glycoprotein Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 3.075, year: 2008

  18. Morin, A Flavonoid, On Lipid Peroxidation And Antioxidant Status In ...

    African Journals Online (AJOL)

    Background: Myocardial infarction affects a large population in the world. Lipid peroxide metabolism plays an important role in the pathology of myocardial infarction. Objective: The present study was designed to investigate the antioxidant potential of morin, a flavonoid in isoproterenol (ISO)-induced myocardial infarction ...

  19. Singlet oxygen reactions with flavonoids. A theoretical-experimental study.

    Directory of Open Access Journals (Sweden)

    Javier Morales

    Full Text Available Detection of singlet oxygen emission, λ(max = 1270 nm, following laser excitation and steady-state methods were employed to measure the total reaction rate constant, k(T, and the reactive reaction rate constant, k(r, for the reaction between singlet oxygen and several flavonoids. Values of k(T determined in deuterated water, ranging from 2.4×10(7 M(-1 s(-1 to 13.4×10(7 M(-1 s(-1, for rutin and morin, respectively, and the values measured for k(r, ranging from 2.8×10(5 M(-1 s(-1 to 65.7×10(5 M(-1 s(-1 for kaempferol and morin, respectively, being epicatechin and catechin chemically unreactive. These results indicate that all the studied flavonoids are good quenchers of singlet oxygen and could be valuable antioxidants in systems under oxidative stress, in particular if a flavonoid-rich diet was previously consumed. Analysis of the dependence of rate constant values with molecular structure in terms of global descriptors and condensed Fukui functions, resulting from electronic structure calculations, supports the formation of a charge transfer exciplex in all studied reactions. The fraction of exciplex giving reaction products evolves through a hydroperoxide and/or an endoperoxide intermediate produced by singlet oxygen attack on the double bond of the ring C of the flavonoid.

  20. Singlet oxygen reactions with flavonoids. A theoretical-experimental study.

    Science.gov (United States)

    Morales, Javier; Günther, Germán; Zanocco, Antonio L; Lemp, Else

    2012-01-01

    Detection of singlet oxygen emission, λ(max) = 1270 nm, following laser excitation and steady-state methods were employed to measure the total reaction rate constant, k(T), and the reactive reaction rate constant, k(r), for the reaction between singlet oxygen and several flavonoids. Values of k(T) determined in deuterated water, ranging from 2.4×10(7) M(-1) s(-1) to 13.4×10(7) M(-1) s(-1), for rutin and morin, respectively, and the values measured for k(r), ranging from 2.8×10(5) M(-1) s(-1) to 65.7×10(5) M(-1) s(-1) for kaempferol and morin, respectively, being epicatechin and catechin chemically unreactive. These results indicate that all the studied flavonoids are good quenchers of singlet oxygen and could be valuable antioxidants in systems under oxidative stress, in particular if a flavonoid-rich diet was previously consumed. Analysis of the dependence of rate constant values with molecular structure in terms of global descriptors and condensed Fukui functions, resulting from electronic structure calculations, supports the formation of a charge transfer exciplex in all studied reactions. The fraction of exciplex giving reaction products evolves through a hydroperoxide and/or an endoperoxide intermediate produced by singlet oxygen attack on the double bond of the ring C of the flavonoid.

  1. Flavonoid metabolites transport across a human BBB model.

    Science.gov (United States)

    Faria, Ana; Meireles, Manuela; Fernandes, Iva; Santos-Buelga, Celestino; Gonzalez-Manzano, Susana; Dueñas, Montserrat; de Freitas, Victor; Mateus, Nuno; Calhau, Conceição

    2014-04-15

    This study aimed to evaluate the transmembrane transport of different flavonoids (flavan-3-ols, anthocyanins and flavonols) and some of their metabolites (methylated and conjugated with glucuronic acid) across hCMEC/D3 cells (a blood-brain barrier (BBB) model). Further metabolism of the tested compounds was assayed and their transport modulated in an attempt to elucidate the mechanisms behind this process. The transport across hCMEC/D3 cells was monitored in basolateral media at 1, 3 and 18 h by HPLC-DAD/MS. All the flavonoids and their metabolites were transported across hCMEC/D3 cells in a time-dependent manner. In general, the metabolites showed higher transport efficiency than the native flavonoid. No further biotransformation of the metabolites was found as consequence of cellular metabolism. Anthocyanins and their metabolites crossed this BBB cell model in a lipophilicity-dependent way. Quercetin transport was influenced by phosphatase modulators, suggesting a phosphorylation/dephosphorylation regulation mechanism. Overall, this work suggests that flavonoids are capable of crossing the BBB and reaching the central nervous system. Copyright © 2013 Elsevier Ltd. All rights reserved.

  2. Dietary Antioxidant and Flavonoid Intakes Are Reduced in the Elderly

    Directory of Open Access Journals (Sweden)

    Małgorzata Elżbieta Zujko

    2015-01-01

    Full Text Available The objective of this study was to determine sources and patterns of antioxidant and flavonoid intakes in the elderly (61–74 yrs in comparison with young (20–40 yrs and middle age (41–60 yrs groups in a cross-sectional study. More than 6000 subjects of both genders, aged 20–74 years, participants of the National Multicenter Health Survey (WOBASZ took part in this study. Daily food consumption was estimated by the single 24-hour dietary recall. Dietary total antioxidant capacity (TAC and flavonoid content (FC were calculated according to the amount of food consumed by the participants combined with antioxidant capacity and flavonoid contents in foods. Food consumption, dietary TAC, and FC were significantly lower in the elderly, especially elderly women in comparison to the young and middle age groups. The consumption of tea, coffee, and apples was associated with the largest contribution to dietary TAC and FC in all participants. Despite high nutrient density of the energy-adjusted diet of ageing people, the elderly consumed the lowest amounts of antioxidants and flavonoids due to the lowest food intake.

  3. Quercitrin: an antileishmanial flavonoid glycoside from Kalanchoe pinnata.

    Science.gov (United States)

    Muzitano, Michelle F; Cruz, Elaine A; de Almeida, Ana Paula; Da Silva, Silvia A G; Kaiser, Carlos R; Guette, Catherine; Rossi-Bergmann, Bartira; Costa, Sônia S

    2006-01-01

    Quercitrin (quercetin 3- O-alpha- L-rhamnopyranoside), one of the constituents of the biologically active aqueous extract obtained from Kalanchoe pinnata, is demonstrated to be a potent antileishmanial compound (IC50 approximately 1 microg/mL) with a low toxicity profile. This is the first time that antileishmanial activity is demonstrated for a flavonoid glycoside.

  4. Flavonoid compounds identified in Alchemilla l. species collected in ...

    African Journals Online (AJOL)

    Rutin (quercetin-3-O-rutinoside) and the flavonoid glycoside, shown as Rf2 were found in all species. Quercitrin and isoquercetin were determined in all analysed species but A. procerrima. Hyperoside was identified in all species except for A. stricta. Vitexin was determined only in A.stricta. Orientin was determined in A.

  5. Extraction and determination of flavonoids in plant materials

    Czech Academy of Sciences Publication Activity Database

    Hohnová, Barbora; Karásek, Pavel; Vespalcová, M.

    2008-01-01

    Roč. 102, č. 15 (2008), s651-s653 ISSN 1803-2389. [Meeting on Chemistry and Life /4./. Brno, 09.09.2008-11.09.2008] R&D Projects: GA ČR GA203/08/1536 Institutional research plan: CEZ:AV0Z40310501 Keywords : PFE * flavonoids Subject RIV: CB - Analytical Chemistry, Separation

  6. Isolated flavonoids against mammary tumour cells LM2.

    Science.gov (United States)

    Carli, Camila B de A; de Matos, Djamile C; Lopes, Flávia C M; Maia, Danielle C G; Dias, Maristela B; Sannomiya, Miriam; Rodrigues, Clenilson M; Andreo, Marcio A; Vilegas, Wagner; Colombo, Lucas L; Carlos, Iracilda Z

    2009-01-01

    The purpose of the present study was to investigate antitumour and anti-inflammatory activities of flavonoids isolated from Byrsonima crassa, Davilla elliptica and Mouriri pusa. The antitumour activity was measured by the MTT assay in murine mammary tumour cells (LM2) and the IC50 values of the flavonoids tested ranged from (31.5 +/- 2.97) to (203.1 +/- 5.9) microg/ml. The flavonoids 1 (myricetin-3-O-alpha-L-rhamnopyranoside) and 3 (quercetin-3-O-galactopyranoside) from D. elliptica were the most active ones against the tumour cells. The same samples were tested to determine the inhibition of the release of nitric oxide (NO) and of the tumour necrosis factor-alpha (TNF-alpha) in murine macrophages by the Griess and ELISA sandwich assay, respectively. Almost all the samples showed inhibitory activity to the release of NO but not of TNF-alpha. Of all substances tested, flavonoids 2 (quercetin) and 6 (myricetin) may show promising activity in the treatment of murine breast cancer by immunomodulatory and antiproliferative activities.

  7. Total Phenol amd Flavonoid contents of Crude Extract and Fractions ...

    African Journals Online (AJOL)

    Phenolic compounds are numerous in plants and are essential part of human diet. Picralima nitida has been extensively used in African folk medicine especially in West Africa. The present study evaluated the total phenolic and flavonoid contents of the extract and fractions of Picralima nitida. The methanol extracts of P.

  8. FLAVONOIDS IN THE GRASS OF TRIBULUS TERRESTRIS L.

    Directory of Open Access Journals (Sweden)

    P. E. Khudenko

    2015-01-01

    Full Text Available The article presents active parts of Tribulus terrestris L. as a perspective sample for study. We have provided an example of flavo-noids determination with high-performance liquid chromatography / MS at the Waters Acquility chromatographer with tandem quad-rupolar MS-detector TQD (Waters.

  9. Influence of Flavonoids on Mechanism of Modulation of Insulin Secretion.

    Science.gov (United States)

    Soares, Juliana Mikaelly Dias; Pereira Leal, Ana Ediléia Barbosa; Silva, Juliane Cabral; Almeida, Jackson R G S; de Oliveira, Helinando Pequeno

    2017-01-01

    The development of alternatives for insulin secretion control in vivo or in vitro represents an important aspect to be investigated. In this direction, natural products have been progressively explored with this aim. In particular, flavonoids are potential candidates to act as insulin secretagogue. To study the influence of flavonoid on overall modulation mechanisms of insulin secretion. The research was conducted in the following databases and platforms: PubMed, Scopus, ISI Web of Knowledge, SciELO, LILACS, and ScienceDirect, and the MeSH terms used for the search were flavonoids, flavones, islets of Langerhans, and insulin-secreting cells. Twelve articles were included and represent the basis of discussion on mechanisms of insulin secretion of flavonoids. Papers in ISI Web of Knowledge were in number of 1, Scopus 44, PubMed 264, ScienceDirect 511, and no papers from LILACS and SciELO databases. According to the literature, the majority of flavonoid subclasses can modulate insulin secretion through several pathways, in an indication that corresponding molecule is a potential candidate for active materials to be applied in the treatment of diabetes. The action of natural products on insulin secretion represents an important investigation topic due to their importance in the diabetes controlIn addition to their typical antioxidant properties, flavonoids contribute to the insulin secretionThe modulation of insulin secretion is induced by flavonoids according to different mechanisms. Abbreviations used: K ATP channels: ATP-sensitive K + channels, GLUT4: Glucose transporter 4, ERK1/2: Extracellular signal-regulated protein kinases 1 and 2, L-VDCCs: L-type voltage-dependent Ca +2 channels, GLUT1: Glucose transporter 1, AMPK: Adenosine monophosphate-activated protein kinase, PTP1B: Protein tyrosine phosphatase 1B, GLUT2: Glucose transporter 2, cAMP: Cyclic adenosine monophosphate, PKA: Protein kinase A, PTK: Protein tyrosine kinase, CaMK II: Ca 2+ /calmodulin

  10. Impact of Plant-Derived Flavonoids on Neurodegenerative Diseases.

    Science.gov (United States)

    Costa, Silvia Lima; Silva, Victor Diogenes Amaral; Dos Santos Souza, Cleide; Santos, Cleonice Creusa; Paris, Irmgard; Muñoz, Patricia; Segura-Aguilar, Juan

    2016-07-01

    Neurodegenerative disorders have a common characteristic that is the involvement of different cell types, typically the reactivity of astrocytes and microglia, characterizing gliosis, which in turn contributes to the neuronal dysfunction and or death. Flavonoids are secondary metabolites of plant origin widely investigated at present and represent one of the most important and diversified among natural products phenolic groups. Several biological activities are attributed to this class of polyphenols, such as antitumor activity, antioxidant, antiviral, and anti-inflammatory, among others, which give significant pharmacological importance. Our group have observed that flavonoids derived from Brazilian plants Dimorphandra mollis Bent., Croton betulaster Müll. Arg., e Poincianella pyramidalis Tul., botanical synonymous Caesalpinia pyramidalis Tul. also elicit a broad spectrum of responses in astrocytes and neurons in culture as activation of astrocytes and microglia, astrocyte associated protection of neuronal progenitor cells, neuronal differentiation and neuritogenesis. It was observed the flavonoids also induced neuronal differentiation of mouse embryonic stem cells and human pluripotent stem cells. Moreover, with the objective of seeking preclinical pharmacological evidence of these molecules, in order to assess its future use in the treatment of neurodegenerative disorders, we have evaluated the effects of flavonoids in preclinical in vitro models of neuroinflammation associated with Parkinson's disease and glutamate toxicity associated with ischemia. In particular, our efforts have been directed to identify mechanisms involved in the changes in viability, morphology, and glial cell function induced by flavonoids in cultures of glial cells and neuronal cells alone or in interactions and clarify the relation with their neuroprotective and morphogetic effects.

  11. Interaction of flavonoids, the naturally occurring antioxidants with different media: A UV-visible spectroscopic study

    Science.gov (United States)

    Naseem, Bushra; Shah, S. W. H.; Hasan, Aurangzeb; Sakhawat Shah, S.

    2010-04-01

    Quantitative parameters for interaction of flavonoids—the naturally occurring antioxidants, with solvents and surfactants are determined using UV-visible absorption spectroscopy. The availability of flavonoids; kaempferol, apigenin, kaempferide and rhamnetin in micelles of sodium dodecyl sulfate (SDS) is reflected in terms of partition coefficient, Kc. Thermodynamic calculations show that the process of transfer of flavonoid molecules to anionic micelles of SDS is energy efficient. A distortion in flavonoid's morphology occurs in case of kaempferol and apigenin in surfactant and water, exhibited in terms of a new band in the UV region of electronic spectra of these flavonoids. The partition coefficients of structurally related flavonoids are correlated with their antioxidant activities.

  12. Ocorrência de flavonas, flavonóis e seus glicosídeos em espécies do gênero Solanum (Solanaceae Occurrence of flavones and flavonols aglycones and its glycosides in Solanum (Solanaceae

    Directory of Open Access Journals (Sweden)

    Tania Maria Sarmento da Silva

    2003-08-01

    Full Text Available During the last decades several flavonoids of Solanum species have been isolated. This review describes the flavones, flavonols and their glycosides presently known as constituents of Solanum species.

  13. Metabolomics analysis reveals the metabolic and functional roles of flavonoids in light-sensitive tea leaves.

    Science.gov (United States)

    Zhang, Qunfeng; Liu, Meiya; Ruan, Jianyun

    2017-03-20

    As the predominant secondary metabolic pathway in tea plants, flavonoid biosynthesis increases with increasing temperature and illumination. However, the concentration of most flavonoids decreases greatly in light-sensitive tea leaves when they are exposed to light, which further improves tea quality. To reveal the metabolism and potential functions of flavonoids in tea leaves, a natural light-sensitive tea mutant (Huangjinya) cultivated under different light conditions was subjected to metabolomics analysis. The results showed that chlorotic tea leaves accumulated large amounts of flavonoids with ortho-dihydroxylated B-rings (e.g., catechin gallate, quercetin and its glycosides etc.), whereas total flavonoids (e.g., myricetrin glycoside, epigallocatechin gallate etc.) were considerably reduced, suggesting that the flavonoid components generated from different metabolic branches played different roles in tea leaves. Furthermore, the intracellular localization of flavonoids and the expression pattern of genes involved in secondary metabolic pathways indicate a potential photoprotective function of dihydroxylated flavonoids in light-sensitive tea leaves. Our results suggest that reactive oxygen species (ROS) scavenging and the antioxidation effects of flavonoids help chlorotic tea plants survive under high light stress, providing new evidence to clarify the functional roles of flavonoids, which accumulate to high levels in tea plants. Moreover, flavonoids with ortho-dihydroxylated B-rings played a greater role in photo-protection to improve the acclimatization of tea plants.

  14. Dietary flavonoids of Spanish youth: intakes, sources, and association with the Mediterranean diet

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    Rowaedh Ahmed Bawaked

    2017-05-01

    Full Text Available Background Plant-based diets have been linked to high diet quality and reduced risk of cardiovascular diseases. The health impact of plant-based diets might be partially explained by the concomitant intake of flavonoids. Estimation of flavonoids intake in adults has been important for the development of dietary recommendations and interventions for the prevention of weight gain and its consequences. However, estimation of flavonoids intake in children and adolescents is limited. Methods Average daily intake and sources of flavonoids were estimated for a representative national sample of 3,534 children and young people in Spain, aged 2–24 years. The data was collected between 1998 and 2000 by 24-h recalls. The Phenol-Explorer database and the USDA database on flavonoids content were used. Adherence to the Mediterranean diet was measured by the KIDMED index. Results The mean and median intakes of total flavonoids were 70.7 and 48.1 mg/day, respectively. The most abundant flavonoid class was flavan-3-ols (35.7%, with fruit being the top food source of flavonoids intake (42.8%. Total flavonoids intake was positively associated with the KIDMED index (p < 0.001. Conclusion The results of this study provide primary information about flavonoids intake and main food sources in Spanish children, adolescents and young adults. Participants with high daily mean intake of flavonoids have higher adherence to the Mediterranean diet.

  15. Flavonoid engineering of flax potentiate its biotechnological application

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    Prescha Anna

    2011-01-01

    Full Text Available Abstract Background Flavonoids are a group of secondary plant metabolites important for plant growth and development. They show also a protective effect against colon and breast cancer, diabetes, hypercholesterolemic atherosclerosis, lupus nephritis, and immune and inflammatory reactions. Thus, overproduction of these compounds in flax by genetic engineering method might potentiate biotechnological application of these plant products. Results Flax plants of third generation overexpressing key genes of flavonoid pathway cultivated in field were used as plant material throughout this study. The biochemical properties of seed, oil and seedcake extracts and fibre from natural and transgenic flax plants were compared. The data obtained suggests that the introduced genes were stably inherited and expressed through plant generations. Overproduction of flavonoid compounds resulted in increase of fatty acids accumulation in oil from transgenic seeds due to protection from oxidation offered during synthesis and seed maturation. The biochemical analysis of seedcake extracts from seeds of transgenic flax revealed significant increase in flavonoids (kaempferol, phenolic acids (coumaric, ferulic, synapic acids and lignan content. Fibres, another product of flax plant showed increase in the level of catechine and acetylvanillone and decrease in phenolic acids upon flax modification. Biochemical analysis results were confirmed using IR spectroscopy. The integral intensities of IR bands have been used for identification of the component of phenylpropanoid pathway in oil, seedcake extract and fibre from control and transgenic flax. It was shown that levels of flavonoids, phenolic acids and lignans in oil and seedcake extract was higher in transgenic flax products compared to control. An FT-IR study of fibres confirmed the biochemical data and revealed that the arrangement of the cellulose polymer in the transgenic fibres differs from the control; in particular a

  16. Chemical profiling of Ocimum americanum using external flavonoids.

    Science.gov (United States)

    Vieira, Roberto F; Grayer, Renée J; Paton, Alan J

    2003-07-01

    A HPLC survey was undertaken of the external flavonoids in 111 herbarium specimens of Ocimum americanum L. (O. canum Sims), which were largely collected from their natural habitats throughout Africa and Asia. The purpose of this study was to establish the flavonoid profiles of this species over the full range of its geographic distribution in order to use these for authentication purposes. Six different external flavonoid chemotypes were found. The major chemotype, present in circa 80% of the specimens of both var. americanum and var. pilosum collected throughout the distribution area of the species, was characterised by very high levels of nevadensin, slightly lower levels of salvigenin and much lower levels of up to 15 other external flavones. Of the remaining five chemotypes, two were found in var. americanum and three in var. pilosum. All specimens belonging to these chemotypes were collected in South or East Africa and represented by only a few specimens. These samples contained much smaller levels of flavones than present in the major chemotype of O. americanum and all lacked nevadensin. Xanthomicrol, a compound absent from the main chemotype, was the dominant flavone in two of the minor chemotypes. The external flavonoid profiles found in the six chemotypes of O. americanum were compared with those of O. x citriodorum (11 herbarium specimens studied) and seven other closely related species of Ocimum. The main nevadensin/salvigenin pattern present in O. americanum was also found in O. x citriodorum, O. basilicum and some specimens of O. minimum, but there were strong quantitative differences in external flavonoids among these taxa. The other chemotypes of O. americanum showed some similarities in their external flavone profiles to those found in the closely related East African species O. fischeri, O. forskolei, O. kenyense and O. kilimandscharicum, which occur in the same geographic areas. This suggests that the uncommon chemotypes of O. americanum may have

  17. Aktivitas antibakteri flavonoid propolis Trigona sp terhadap bakteri Streptococcus mutans (in vitro (In vitro antibacterial activity of flavonoids Trigona sp propolis against Streptococcus mutans

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    Ardo Sabir

    2005-09-01

    Full Text Available A number of investigations have shown a positive correlation between the number of Streptococcus mutans (S. mutans in dental plaque and the prevalence of dental caries. Consequently, this microorganism has been the prime target for the prevention of dental caries. Propolis being a substance made by the honeybee, is a potent antibacterial agent. The main chemical class present in propolis is flavonoids. Flavonoids are well-known plant compounds that have antibacterial property. Because S. mutans is accepted to be one of the microorganisms responsible for dental caries and flavonoids in propolis are antibacterial, the purpose of this study was to evaluate in vitro the antibacterial activity of flavonoids Trigona sp propolis against S. mutans as a first step in its possible use as an alternative anticaries agent. Extract flavonoids was purified from ethanol extract of propolis which was obtained from Bulukumba Regency South Sulawesi using thin layer chromatography. The purification of flavonoids was carried-out by UVradiation at λ max 254 nm and λmax 366 nm and treatment with ammonia. Extract flavonoids was diluted in aquadest to 0.05%; 0.075%; 0.1%; 0.25%; 0.5%; 0.75% concentrations. Aquadest and 10% Povidone iodine were also used as control solution. S mutans were grown in medium glucose nutrient agar and incubated with flavonoids for 24 and 48 hours, at 37° C. Antibacterial activity was reflected by the diameter of the inhibition zones around the stainless steel cylinder. The data were analyzed by using ANOVA followed by LSD test with significance level of 5%. The results of this study showed that after being incubated for 24 and 48 hours, all flavonoid concentrations significantly (p < 0.05 inhibited the growth of S mutans. 0.1% flavonoid was the most effective concentration to inhibit the growth of S mutans after 24 hours of incubation and 0.5% flavonoid after 48 hours of incubator.

  18. Anti-inflammatory Flavonoids Isolated from Passiflora foetida.

    Science.gov (United States)

    Nguyen, Thi Yen; To, Dao Cuong; Tran, Manh Hung; Lee, Joo Sang; Lee, Jeong Hyung; Kim, Jeong Ah; Woo, Mi Hee; Min, Byung Sun

    2015-06-01

    In this study, we evaluated the anti-inflammatory activity of the soluble ethyl acetate fraction and chemical components of the stem bark of Passiflora foetida (Passifloraceae). Ten flavonoids (1-10) were isolated by various chromatographic techniques, and their structures were determined based on spectroscopic analyses by using nuclear magnetic resonance (NMR). Luteolin (2) and chrysoeriol (3) showed the most potent inhibition of nitric oxide (NO) production in macrophage cell line, RAW264.7, with half maximal inhibitor concentration (IC50) values of 1.2 and 3.1 μM, respectively. These compounds suppressed lipopolysaccharide (LPS)-induced inducible NO synthase (iNOS) expression at the transcription level. Our research indicates that the stem bark of P. foetida has significant anti-inflammatory properties, suggesting that its flavonoids may have anti-inflammatory benefits.

  19. Flavonoid glycosides from Erythroxylum pulchrum A. St.-Hil. (Erythroxylaceae)

    International Nuclear Information System (INIS)

    Albuquerque, Camila Holanda de; Tavares, Josean Fechine; Oliveira, Steno Lacerda de; Silva, Taina Souza; Costa, Vicente Carlos de Oliveira; Silva, Marcelo Sobral da; Goncalves, Gregorio Fernandes; Pessoa, Hilzeth de Luna Freire; Agra, Maria de Fatima

    2014-01-01

    The phytochemical investigation of Erythroxylum pulchrum St. Hil. (Erythroxylaceae) led to the isolation of three known flavonoid glycosides quercetin-3-O-α-L-rhaminoside, ombuin-3-ruthinoside and ombuin-3-ruthinoside-5-glucoside. These flavonoids are being described for the first time in this E. pulchrum. The structures of the compounds were determined by analysis of IR, MS and NMR data, as well as by comparison with literature data. The methanolic extract of leaves from E. pulchrum inhibited the growth of the Bacillus subtilis CCT 0516, Escherichia coli ATCC 2536, Pseudomonas aeruginosa ATCC 8027, P. aeruginosa ATCC 25619, Staphylococcus aureus ATCC 6538, S. aureus ATCC 25925, Streptococcus sanguinis ATCC 15300, S. salivarius ATCC 7073, S. mutans ATCC 25175 and Streptococcus ATCC. S. aureus ATCC 25925 was the most sensitive among the other S. sanguinis while S. salivarius proved the most resistant. (author)

  20. Dirhamnosyl flavonoid and other constituents from Brillantaisia palisatii

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    Luciane Fátima Berrondo

    2003-12-01

    Full Text Available A mixture containing sitosterol and stigmasterol; a new triterpene 3-epi-ursolic acid; another triterpene mixture comprising a-amyrin, b-amyrin and lupeol; verbascoside, a phenylpropanoid glycoside; and lespedin, a glycosyl flavonoid, were isolated. The less polar compounds (steroids and triterpenoids were isolated from the hexane partition of the crude ethanolic extract while the more polar ones (phenylpropanoid glycoside and glycosyl flavonoid were isolated from the ethyl acetate partition of the same extract. The structures of all compounds were established using modern spectrometric methods of elucidation. The spectroscopic data of Lespedin, a rare dirhamnosylflavonol with hypotensor activity and of the triterpene, 3-epi-ursolic acid, are also reported.

  1. Microbial production of the flavonoids garbanzol, resokaempferol and fisetin

    OpenAIRE

    Stahlhut, Steen Gustav; Siedler, Solvej; Neves, Ana Rute; MAURY,, JEROME; Förster, Jochen; Gaspar, Paula; Borodina, Irina; Rodriguez Prado, Edith Angelica; Strucko, Tomas

    2016-01-01

    The invention provides a genetically modified micro-organism comprising one or more transgene for the production of one or more of the flavonoids garbanzol, resokaempferol and fisetin. The micro-organism may be a bacterial or yeast cell engineered to express a metabolic pathway for garbanzol, resokaempferol and/or fisetin biosynthesis. The invention further provides a method for producing garbanzol, resokaempferol and/or fisetin employing the genetically modified micro-organism of the inventi...

  2. Mutagenicity of Flavonoids Assayed by Bacterial Reverse Mutation (Ames Test

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    Eliana Aparecida Varanda

    2012-05-01

    Full Text Available The mutagenicity of ten flavonoids was assayed by the Ames test, in Salmonella typhimurium strains TA98, TA100 and TA102, with the aim of establishing hydroxylation pattern-mutagenicity relationship profiles. The compounds assessed were: quercetin, kaempferol, luteolin, fisetin, chrysin, galangin, flavone, 3-hydroxyflavone, 5-hydroxyflavone and 7-hydroxyflavone. In the Ames assay, quercetin acted directly and its mutagenicity increased with metabolic activation. In the presence of S9 mix, kaempferol and galangin were mutagenic in the TA98 strain and kaempferol showed signs of mutagenicity in the other strains. The absence of hydroxyl groups, as in flavone, only signs of mutagenicity were shown in strain TA102, after metabolization and, among monohydroxylated flavones (3-hydroxyflavone, 5-hydroxyflavone and 7-hydroxyflavone, the presence of hydroxyl groups only resulted in minor changes. Luteolin and fisetin also showed signs of mutagenicity in strain TA102. Finally, chrysin, which has only two hydroxy groups, at the 5-OH and 7-OH positions, also did not induce mutagenic activity in any of the bacterial strains used, under either activation condition. All the flavonoids were tested at concentrations varying from 2.6 to 30.7 nmol/plate for galangin and 12.1 to 225.0 nmol/plate for other flavonoids. In light of the above, it is necessary to clarify the conditions and the mechanisms that mediate the biological effects of flavonoids before treating them as therapeutical agents, since some compounds can be biotransformed into more genotoxic products; as is the case for galangin, kaempferol and quercetin.

  3. The oxidation of luteolin, the natural flavonoid dye

    Czech Academy of Sciences Publication Activity Database

    Ramešová, Šárka; Sokolová, Romana; Tarábek, Ján; Degano, I.

    2013-01-01

    Roč. 110, NOV 2013 (2013), s. 646-654 ISSN 0013-4686 R&D Projects: GA ČR GA203/09/1607 Grant - others:Rada Programu interní podpory projektů mezinárodní spolupráce AV ČR(CZ) M200401201 Program:M Institutional support: RVO:61388955 ; RVO:61388963 Keywords : oxidation * flavonoids * luteolin Subject RIV: CG - Electrochemistry Impact factor: 4.086, year: 2013

  4. Effect of precursors on flavonoid production by Hydrocotyle ...

    African Journals Online (AJOL)

    Callus tissue of Hydrocotyle bonariensis was initiated from the leaf of H. bonariensis treated with 2 mg/l of 2,4-dichlorophenoxyacetic acid (2,4-D) and 1 mg/l kinetin. The culture was kept at 25°C, under light (cool white fluorescent tubes, 1200 lux). To optimize the precursors to increase the production of flavonoid, different ...

  5. Phytochemical study of the flavonoids of acacia nilotica var astringens

    International Nuclear Information System (INIS)

    El Gazali, N. A.

    2006-08-01

    The barks of acaica nilotica var astringens were extracted with 95% ethanol. Qualitative tests on the alcoholic extractives were negative for alkaloids and positive for steroids, tannins and flavonoids. Fractionation of the alcoholic extract over silica gel using acetone: methanol (4:1) gave a pure compound-compound 1. The structure of compound 1 was deduced on the basis of its IR, UV, NMR and mass spectra and the following structure was suggested.(Author)

  6. Flavonoids and Melanins: A Common Strategy across Two Kingdoms

    OpenAIRE

    Carletti, Giorgia; Nervo, Giuseppe; Cattivelli, Luigi

    2014-01-01

    Ultraviolet (UV) radiations alter a number of metabolic functions in vivant. They produce damages to lipids, nucleic acids and proteins, generating reactive oxygen species such as singlet oxygen (O2), hydroxyl radical (HO) and superoxide anion (O2 -). Plants and animals, after their water emersion, have developed biochemical mechanisms to protect themselves from that environmental threat through a common strategy. Melanins in animals and flavonoids in plants are antioxidant pigments acting as...

  7. Citrus Flavonoid Supplementation Improves Exercise Performance in Trained Athletes

    Directory of Open Access Journals (Sweden)

    Elvera Overdevest, Jeroen A. Wouters, Kevin H.M. Wolfs, Job J.M. van Leeuwen, Sam Possemiers

    2018-03-01

    Full Text Available Previous studies have shown that polyphenol supplementation may be an effective strategy to improve exercise performance, due to their antioxidant character and ability to stimulate NO production. These properties may contribute to exercise performance, yet no conclusive research has been performed in exploring the direct effects of citrus flavonoids on human exercise performance. Therefore, the purpose of this study was to assess whether supplementation of a customized citrus flavonoid (CF extract for 4 weeks improves cycling time-trial performance in trained male athletes. In a double-blind, randomized, parallel study, 39 healthy, trained males were given a daily dose of either 500 mg of a customized citrus flavonoid extract (CF or a placebo for 4 weeks. Exercise performance was tested by means of a time-trial test on a cycle ergometer, during which participants had to generate as much power as possible for duration of 10 minutes. Absolute power output significantly increased with 14.9 ± 3.9 W after 4 weeks of CF supplementation, corresponding with a 5.0% increase, compared to 3.8 ± 3.2 W (1.3% increase in placebo (p < 0.05. In addition, oxygen consumption/power ratio significantly decreased in the CF group compared to placebo (p = 0.001, and a trend was found in the change in peak power output in CF (18.2 ± 23.2 W versus placebo (-28.4 ± 17.6 W; p = 0.116. The current study is the first convincing report that citrus flavonoid supplementation can improve exercise performance, as shown by a significant increase in power output during the exercise test.

  8. BIOLOGICAL ACTIVITIES AND PHENOLIC-FLAVONOID CONTENTS OF BILBERRY EXTRACTS

    OpenAIRE

    I. HACIBEKİROĞLU, U. KOLAK*, I. HACIBEKİROĞLU, U. KOLAK*

    2014-01-01

    SUMMARYIn this study, the petroleum ether, dichloromethane, methanol and hot water extracts were prepared from bilberry blooms. Total phenolic and flavonoid contents of these extracts were determined as pyrocatechol and quercetin equivalents, respectively. The antioxidant activity of the extracts was investigated by using four methods including DPPH free radical and ABTS cation radical scavenging, β-carotene bleaching and cupric reducing antioxidant capacity (CUPRAC) assays. The methanol ext...

  9. Analysis of Flavonoids in Rhamnus davurica and Its Antiproliferative Activities

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    Guilin Chen

    2016-09-01

    Full Text Available Rhamnus davurica Pall. (R. davurica has been used as a traditional medicinal herb for many years in China and abroad. It has been well documented as a rich source of flavonoids with diversified structures, which in turn results in far-ranging biological activities, such as anti-inflammation, anticancer, antibacterial and antioxidant activities. In order to further correlate their anticancer potentials with the phytochemical components, the fingerprint profile of R. davurica herb from Dongbei was firstly investigated using HPLC-ESI-MS/MS. Thirty two peaks were detected and identified, 14 of which were found in R. davurica for the first time in this work. Furthermore, a total of 23 peaks were resolved as flavonoids, which are the major components found in R. davurica. Meanwhile, the antiproliferative activities against human cancer cells of HT-29 and SGC-7901 in vitro exhibited distinct inhibitory effects with IC50 values at 24.96 ± 0.74 and 89.53 ± 4.11 μg/mL, respectively. Finally, the general toxicity against L-O2 cells displayed a much higher IC50 at 229.19 ± 8.52 μg/mL, which suggested very low or no toxicity on hepatic cell viability. The current study revealed for the first time the correlations between the flavonoids of R. davurica with their antiproliferative activities, which indicated that the fingerprint profile of flavonoids and their anticancer activities could provide valuable information on the quality control for herbal medicines and their derived natural remedies from this valuable medicinal plant.

  10. Brain Protection and Cognitive Function: Cocoa Flavonoids as Nutraceuticals.

    Science.gov (United States)

    Grassi, Davide; Ferri, Claudio; Desideri, Giovambattista

    2016-01-01

    Cognitive decline and dementia are major public health social problems, suggesting the specific need to provide research into risk factors for cognitive decline as priority topic. Increasing evidence supports the hypothesis that oxidative stress and neuroinflammation might play a crucial role in the pathophysiology of cognitive decline. Further, cognitive dysfunction and dementia in Alzheimer's disease as well as in vascular dementia seem to be also the consequence of cerebral blood flow decrease and deregulation, also suggesting a putative pathophysiological convergence of mechanisms between atherosclerosis and Alzheimer's disease. In keeping with this, a growing interest has been addressed to flavonoids as potential nutraceuticals with neuroprotective effects. Of interest, cocoa beans have been described as a fundamental source of anti-oxidant flavonoids with the flavan-3-ols and their derivatives being present in high concentrations. Therefore, recent studies specifically focused on the favorable effects of flavonoid-rich cocoa and chocolate on cerebrovascular risk factors and cognitive function. Aim of this review is to summarize new findings concerning the cocoa effects on cognitive function, particularly focusing on some putative mechanisms of vascular and antioxidant action involved in preventing dementia.

  11. Antiproliferative Activity of Flavonoids from Croton sphaerogynus Baill. (Euphorbiaceae

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    Kátia Pereira dos Santos

    2015-01-01

    Full Text Available Croton sphaerogynus is a shrub from the Atlantic Rain Forest in southeastern Brazil. A lyophilized crude EtOH extract from leaves of C. sphaerogynus, obtained by maceration at room temperature (seven days, was suspended in methanol and partitioned with hexane. The purified MeOH phase was fractionated over Sephadex LH-20 yielding five fractions (F1–F5 containing flavonoids, as characterized by HPLC-DAD and HPLC-MS analyses. The antiproliferative activity of the crude EtOH extract, MeOH and hexane phases, and fractions F1–F5 was evaluated on in vitro cell lines NCI-H460 (nonsmall cell lung, MCF-7 (breast cancer, and U251 (glioma. The MeOH phase showed activity (mean log GI50 0.54 higher than the hexane phase and EtOH extract (mean log GI50 1.13 and 1.19, resp.. F1 exhibited activity against NCI-H460 (nonsmall cell lung (GI50 1.2 μg/mL, which could be accounted for the presence of flavonoids and/or diterpenes. F4 showed moderate activity (mean log GI50 1.05, while F5 showed weak activity (mean log GI50 1.36. It is suggested that the antiproliferative activity of the crude EtOH extract and MeOH phase is accounted for a synergistic combination of flavonoids and diterpenes.

  12. Antiproliferative Activity of Flavonoids from Croton sphaerogynus Baill. (Euphorbiaceae)

    Science.gov (United States)

    dos Santos, Kátia Pereira; Motta, Lucimar B.; Santos, Deborah Y. A. C.; Salatino, Maria L. F.; Salatino, Antonio; Ferreira, Marcelo J. Pena; Lago, João Henrique G.; Ruiz, Ana Lúcia T. G.; de Carvalho, João E.; Furlan, Cláudia M.

    2015-01-01

    Croton sphaerogynus is a shrub from the Atlantic Rain Forest in southeastern Brazil. A lyophilized crude EtOH extract from leaves of C. sphaerogynus, obtained by maceration at room temperature (seven days), was suspended in methanol and partitioned with hexane. The purified MeOH phase was fractionated over Sephadex LH-20 yielding five fractions (F1–F5) containing flavonoids, as characterized by HPLC-DAD and HPLC-MS analyses. The antiproliferative activity of the crude EtOH extract, MeOH and hexane phases, and fractions F1–F5 was evaluated on in vitro cell lines NCI-H460 (nonsmall cell lung), MCF-7 (breast cancer), and U251 (glioma). The MeOH phase showed activity (mean log GI50 0.54) higher than the hexane phase and EtOH extract (mean log GI50 1.13 and 1.19, resp.). F1 exhibited activity against NCI-H460 (nonsmall cell lung) (GI50 1.2 μg/mL), which could be accounted for the presence of flavonoids and/or diterpenes. F4 showed moderate activity (mean log GI50 1.05), while F5 showed weak activity (mean log GI50 1.36). It is suggested that the antiproliferative activity of the crude EtOH extract and MeOH phase is accounted for a synergistic combination of flavonoids and diterpenes. PMID:26075219

  13. Complexation of Flavonoids with Iron: Structure and Optical Signatures

    Science.gov (United States)

    Ren, Jun; Meng, Sheng; Lekka, Ch. E.; Kaxiras, Efthimios

    2008-03-01

    Flavonoids exhibit antioxidant behavior believed to be related to their metal ion chelation ability. We investigate the complexation mechanism of several flavonoids, quercetin, luteolin, galangin, kaempferol and chrysin with iron, the most abundant type of metal ions in the body, through first- principles electronic structure calculations based on Density Functional Theory (DFT). We find that the most likely chelation site for Fe is the 3-hydroxyl-4-carbonyl group, followed by 4- carbonyl-5-hydroxyl group and the 3'-4' hydroxyl (if present) for all the flavonoid molecules studied. Three quercetin molecules are required to saturate the bonds of a single Fe ion by forming six orthogonal Fe-O bonds, though the binding energy per molecule is highest for complexes consisting of two quercetin molecules and one Fe atom, in agreement with experiment. Optical absorption spectra calculated with time- dependent DFT serve as signatures to identify various complexes. For the iron-quercetin complexes, we find a redshift of the first absorbance peak upon complexation in good agreement with experiment; this behavior is explained by the narrowing of the optical gap of quercetin due to Fe(d)--O(p) orbital hybridization.

  14. 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.

  15. Antigenotoxic prenylated flavonoids from stem bark of Erythrina latissima.

    Science.gov (United States)

    Zarev, Yancho; Foubert, Kenn; Lucia de Almeida, Vera; Anthonissen, Roel; Elgorashi, Esameldin; Apers, Sandra; Ionkova, Iliana; Verschaeve, Luc; Pieters, Luc

    2017-09-01

    A series of prenylated flavonoids was obtained from antigenotoxic extracts and fractions of stem bark of Erythrina latissima E. Mey (Leguminosae). In addition to five constituents never reported before, i.e. (2S)-5,7-dihydroxy-2-(4-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-6-yl)chroman-4-one (erylatissin D), (2S)-5,7-dihydroxy-2-(4-methoxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-6-yl)chroman-4-one (erylatissin E), 5,7-dihydroxy-3-(4-methoxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-6-yl)-4H-chromen-4-one (erylatissin F), (2S)-5,7,8'-trihydroxy-2',2'-dimethyl-[2,6'-bichroman]-4-one (erylatissin G) and (2S)-5,7-dihydroxy-8'-methoxy-2',2'-dimethyl-[2,6'-bichroman]-4-one (dihydroabyssinin I), 18 known flavonoids were identified. Evaluation of the antigenotoxic properties (against genotoxicity induced by aflatoxin B1, metabolically activated) in the Vitotox assay revealed that most flavonoids were active. Sigmoidin A and B showed the highest activity, with an IC 50 value of 18.7 μg/mL, equivalent to that of curcumin (IC 50 18.4 μg/mL), used as a reference antigenotoxic compound. Copyright © 2017 Elsevier Ltd. All rights reserved.

  16. Flavonoids and Chagas' Disease: The Story So Far!

    Science.gov (United States)

    Nabavi, Seyed Fazel; Sureda, Antoni; Daglia, Maria; Izadi, Morteza; Rastrelli, Luca; Nabavi, Seyed Mohammad

    2017-01-01

    Chagas disease is one of the major health problems in Central and South America, which is caused by the parasitic protozoa, Trypanosoma cruzi. It is commonly transmitted by members of blood-sucking subfamily Triatominae. Chagas disease is associated with cardiac and gastrointestinal manifestations. Up to now, there are no effective vaccines for treatment of Chagas disease and benznidazole and nifurtimox are the only effective anti-Chagas drugs that cause different adverse and side effects. Therefore, much attention has been paid to natural products as novel therapeutic strategies for Chagas disease and its manifestations. Nowadays, some flavonoids could be considered as effective and safe bioactive natural products with potential anti-Chagas activity. Despite the increasing evidence, there is lack of review papers regarding the beneficial effects of flavonoids against Chagas disease and its manifestations. The aim of this paper is to review the available scientific data on the beneficial effects of flavonoids on Chagas disease and its manifestations published over the past two decades. Moreover, we provide an overview on etiology, transmission, epidemiology, clinical manifestations, and current treatment protocols of Chagas disease.

  17. Structure characteristics for intestinal uptake of flavonoids in Caco-2 cells.

    Science.gov (United States)

    Fang, Yajing; Liang, Fuqiang; Liu, Kunyuan; Qaiser, Shakeel; Pan, Siyi; Xu, Xiaoyun

    2018-03-01

    Flavonoids are a large group of polyphenols and widely distributed in plant foods. Flavonoids exhibit various biological activities, such as anti-cancer, antioxidant and anti-inflammatory while poor oral bioavailability has been considered as a major hurdle in their use as functional foods. Cellular uptake and efflux of flavonoid implicates their bioavailability. To investigate the cellular uptake and efflux of flavonoids, 27 flavonoids were measured for their cellular uptake in Caco-2 cells with (CUV) and without (CU) the inhibitor of P-glycoprotein (P-gp) verapamil. Then, a quantitative structure-absorption relationship (QSAR) model containing 21 compounds as training set was obtained from their corresponding CU. The model showed good robustness and predictivity with a high cross-validation coefficient (Q 2 ) value of 0.809 and Log of the octanol/water partition coefficient (SlogP) and atomic charge on carbon 5 (Q C5 ) were related to flavonoid uptake. The CUV of some flavonoids were significantly (ppumped out by P-gp. The structure-affinity relationship of flavonoids as substrates of P-gp was determined with the presence of 4'-OCH 3 , 3'-OCH 3 and the absence of 3'-OH, 3-OH and 4'-OH favorable for the affinity of flavonoids. These results provide valuable information for screening flavonoids with good absorption and low affinity with transporters. Copyright © 2017. Published by Elsevier Ltd.

  18. Dietary flavonoid derivatives enhance chemotherapeutic effect by inhibiting the DNA damage response pathway

    International Nuclear Information System (INIS)

    Kuo, Ching-Ying; Zupkó, István; Chang, Fang-Rong; Hunyadi, Attila; Wu, Chin-Chung; Weng, Teng-Song; Wang, Hui-Chun

    2016-01-01

    Flavonoids are the most common group of polyphenolic compounds and abundant in dietary fruits and vegetables. Diet high in vegetables or dietary flavonoid supplements is associated with reduced mortality rate for patients with breast cancer. Many studies have been proposed for mechanisms linking flavonoids to improving chemotherapy efficacy in many types of cancers, but data on this issue is still limited. Herein, we report on a new mechanism through which dietary flavonoids inhibit DNA damage checkpoints and repair pathways. We found that dietary flavonoids could inhibit Chk1 phosphorylation and decrease clonogenic cell growth once breast cancer cells receive ultraviolet irradiation, cisplatin, or etoposide treatment. Since the ATR-Chk1 pathway mainly involves response to DNA replication stress, we propose that flavonoid derivatives reduce the side effect of chemotherapy by improving the sensitivity of cycling cells. Therefore, we propose that increasing intake of common dietary flavonoids is beneficial to breast cancer patients who are receiving DNA-damaging chemotherapy, such as cisplatin or etoposide-based therapy. - Highlights: • First report on inhibition of both DNA damage and repair by dietary flavonoids • Dietary flavonoids inhibit cisplatin- and UV-induced Chk1 phosphorylation. • Flavonoids combined with cisplatin or UV treatment show notable growth inhibition. • Promising treatment proposal for patients who are receiving adjuvant chemotherapy

  19. Influence of Intestinal Microbiota on the Catabolism of Flavonoids in Mice.

    Science.gov (United States)

    Lin, Weiqun; Wang, Wenting; Yang, Hai; Wang, Dongliang; Ling, Wenhua

    2016-12-01

    Although in vitro studies have shown that flavonoids are metabolized into phenolic acids by the gut microbiota, the biotransformation of flavonoids by intestinal microbiota is seldom studied in vivo. In this study, we investigated the impact of the gut microbiota on the biotransformation of 3 subclasses of flavonoids (flavonols, flavones, and flavanones). The ability of intestinal microbiota to convert flavonoids was confirmed with an in vitro fermentation model using mouse gut microflora. Simultaneously, purified flavonoids were administered to control and antibiotic-treated mice by gavage, and the metabolism of these flavonoids was evaluated. p-Hydroxyphenylacetic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, hydrocaffeic acid, coumaric acid, and 3-(4-hydroxyphenyl)propionic acid were detected in the serum samples from the control mice after flavonoid consumption. The serum flavonoid concentrations were similar in both groups, whereas the phenolic metabolite concentrations were lower in the antibiotic-treated mice than in the control mice. We detected markedly higher flavonoids excretion in the feces and urine of the antibiotic-treated mice compared to the controls. Moreover, phenolic metabolites were upregulated in the control mice. These results suggest that the intestinal microbiota are not necessary for the absorption of flavonoids, but are required for their transformation. © 2016 Institute of Food Technologists®.

  20. Identification and quantification and antioxidant activity of flavonoids in different strains of silk cocoon, Bombyx mori.

    Science.gov (United States)

    Napavichayanun, Supamas; Lutz, Oliver; Fischnaller, Martin; Jakschitz, Thomas; Bonn, Günther; Aramwit, Pornanong

    2017-10-01

    Silk cocoon is produced from silkworm (Bombyx mori) to protect itself from outer environment. Various strains of cocoon contain different forms and amounts of flavonoids, which may affect on their antioxidant activity. Moreover, the extraction method would influence the amount of flavonoids extracted. Therefore, the objectives of this study were to identify and quantify the flavonoids in 3 strains of bivoltine Bombyx mori silk cocoon (Chul 1/1; white cocoon, Chul 3/2; greenish cocoon, and Chul 4/2; yellow cocoon) extracted by 6 different solvents including acetone, ethyl acetate, dimethyl sulfoxide (DMSO), ethanol, methanol, and purified water. The flavonoids extracted were identified and quantified by liquid chromatography-mass spectrometry (LC-MS). The antioxidant activity of flavonoids extracted was also investigated by visible spectroscopy at 517 nm. The results showed that Chul 3/2 silk cocoon contained the highest amount of flavonoids. Purified water seemed to be the best solvent that preserved most antioxidant activity of the flavonoids extracted. Flavonoids in Chul 1/1 and Chul 4/2 silk cocoon were rarely found, however they contained some antioxidant activities. The data from this study can provide basic information for flavonoid extraction from silk cocoon which can also apply for other flavonoid-containing natural biomaterials. Copyright © 2017 Elsevier Inc. All rights reserved.

  1. Electrochemical study of the increased antioxidant capacity of flavonoids through complexation with iron(II) ions

    International Nuclear Information System (INIS)

    Porfírio, Demóstenes Amorim; Ferreira, Rafael de Queiroz; Malagutti, Andréa Renata; Valle, Eliana Maíra Agostini

    2014-01-01

    Highlights: • Metal-Flavonoid complexes exhibit greater antioxidant capacity than the free flavonoid;. • Voltammetric profile is an additional information for determining antioxidant capacity;. • Pyrogallol group is a stronger complex-forming group than the catechol;. • Morin, quercetin and fisetin increased their antioxidant capacity in 15%, 32% and 28%, respectively. - Abstract: Flavonoids are polyphenolic compounds that act as natural antioxidants in the human body through various mechanisms, with an emphasis on suppressing reactive oxygen species (ROS) formation by inhibiting enzymes, the direct capture of ROS, and the regulation/protection of antioxidant defenses. Additionally, flavonoids can coordinate with transition metals to catalyze electron transport and promote free radical capture. Recently, metal ion chelation mechanisms have generated considerable interest, as experimental data show that flavonoids in metal complexes exhibit greater antioxidant activity than free flavonoids. However, few studies have correlated the complexing properties of flavonoids with their antioxidant capacity. Thus, the aim of this study was to use the CRAC (Ceric Reducing Antioxidant Capacity) electrochemical assay to measure the antioxidant capacity of five free flavonoids and Fe 2+ -flavonoid complexes. In addition, the interactions between the flavonoids and Fe 2+ were analyzed based on the oxidation peaks formed in their cyclic voltammograms

  2. In vitro screening of radioprotective properties in the novel glucosylated flavonoids.

    Science.gov (United States)

    Yu, Hao; Haskins, Jeremy S; Su, Cathy; Allum, Allison; Haskins, Alexis H; Salinas, Victoria A; Sunada, Shigeaki; Inoue, Taisuke; Aizawa, Yasushi; Uesaka, Mitsuru; Kato, Takamitsu A

    2016-11-01

    Novel glucosyl flavonoids are developed by the addition of glucose to naturally occurring flavonoids. Flavonoids are known antioxidants that possess radioprotective properties. In order to investigate the radioprotective properties of novel glucosyl flavonoids, in vitro DNA double-strand breaks (DSBs) analysis was carried out. In the present study, Quercetin, Naringenin, and Hesperetin groups of flavonoids included in the natural and novel glucosyl 13 flavonoids were investigated. Flavonoids were mixed with Lambda DNA, and subsequently exposed to gamma‑rays. Furthermore, DNA DSB yields were visualized by gel electrophoresis. Quercetin derivatives displayed reduced DNA DSB formation at 10 µM. At a high concentration, the majority of flavonoids displayed radioprotective properties as a reduction of DSB yields. Suppression of DSB formation was confirmed via the molecular combing assay for Quercetin, and three monoglucosyl flavonoids. Glucosylation showed positive effects for radioprotection and monoglucosyl-Rutin showed superior radioprotective properties when compared to monoglucosyl-Naringin and Hesperidin. In addition, Quercetin derivatives had greater total antioxidant capacities and DPPH radical scavenging ability than other flavonoid groups. Since Quercetin, Isoquercetin, and Rutin display poor water solubility, monoglucosyl-Rutin, maltooligosyl-Isoquercetin, and maltooligosyl-Rutin may be better radioprotective agents and easily bioavailable with increased water solubility.

  3. Flavonoid glycosides from Erythroxylum pulchrum A. St.-Hil. (Erythroxylaceae); Flavonoides glicosilados de Erythroxylum pulchrum A. St.-Hil. (Erythroxylaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Albuquerque, Camila Holanda de; Tavares, Josean Fechine; Oliveira, Steno Lacerda de; Silva, Taina Souza; Costa, Vicente Carlos de Oliveira; Silva, Marcelo Sobral da, E-mail: josean@ltf.ufpb.br [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil). Centro de Ciencias da Saude. Departamento de Ciencias Farmaceuticas; Goncalves, Gregorio Fernandes; Pessoa, Hilzeth de Luna Freire [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil). Centro de Ciencias da Saude. Dept. de Biologica Molecular; Agra, Maria de Fatima [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil). Centro de Biotecnologia. Departamento de Biotecnologia

    2014-07-01

    The phytochemical investigation of Erythroxylum pulchrum St. Hil. (Erythroxylaceae) led to the isolation of three known flavonoid glycosides quercetin-3-O-α-L-rhaminoside, ombuin-3-ruthinoside and ombuin-3-ruthinoside-5-glucoside. These flavonoids are being described for the first time in this E. pulchrum. The structures of the compounds were determined by analysis of IR, MS and NMR data, as well as by comparison with literature data. The methanolic extract of leaves from E. pulchrum inhibited the growth of the Bacillus subtilis CCT 0516, Escherichia coli ATCC 2536, Pseudomonas aeruginosa ATCC 8027, P. aeruginosa ATCC 25619, Staphylococcus aureus ATCC 6538, S. aureus ATCC 25925, Streptococcus sanguinis ATCC 15300, S. salivarius ATCC 7073, S. mutans ATCC 25175 and Streptococcus ATCC. S. aureus ATCC 25925 was the most sensitive among the other S. sanguinis while S. salivarius proved the most resistant. (author)

  4. Intake of dietary flavonoids and risk of epithelial ovarian cancer.

    Science.gov (United States)

    Cassidy, Aedín; Huang, Tianyi; Rice, Megan S; Rimm, Eric B; Tworoger, Shelley S

    2014-11-01

    The impact of different dietary flavonoid subclasses on risk of epithelial ovarian cancer is unclear, with limited previous studies that have focused on only a few compounds. We prospectively examined associations between habitual flavonoid subclass intake and risk of ovarian cancer. We followed 171,940 Nurses' Health Study and Nurses' Health Study II participants to examine associations between intakes of total flavonoids and their subclasses (flavanones, flavonols, anthocyanins, flavan-3-ols, flavones, and polymeric flavonoids) and risk of ovarian cancer by using Cox proportional hazards models. Intake was calculated from validated food-frequency questionnaires collected every 4 y. During 16-22 y of follow-up, 723 cases of ovarian cancer were confirmed through medical records. In pooled multivariate-adjusted analyses, total flavonoids were not statistically significantly associated with ovarian cancer risk (HR for the top compared with the bottom quintile: 0.85; 95% CI: 0.66, 1.09; P-trend = 0.17). However, participants in the highest quintiles of flavonol and flavanone intakes had modestly lower risk of ovarian cancer than did participants in the lowest quintile, although the P-trend was not significant [HRs: 0.76 (95% CI: 0.59, 0.98; P-trend = 0.11) and 0.79 (95% CI: 0.63,1.00; P-trend = 0.26), respectively]. The association for flavanone intake was stronger for serous invasive and poorly differentiated tumors (comparable HR: 0.68; 95% CI: 0.50, 0.92; P-heterogeneity = 0.10, P-trend = 0.07) compared with nonserous and less-aggressive tumors. Intakes of other subclasses were not significantly associated with risk. In food-based analyses used to compare subjects who consumed >1 and ≤ 1 cup black tea/d, the HR was 0.68 (95% CI: 0.51, 0.90; P intakes of flavonols and flavanones as well as black tea consumption may be associated with lower risk of ovarian cancer. Additional prospective studies are required to confirm these findings.

  5. Cytotoxicity of flavonoid glycosides, flavonoids and phenolic acids from Inula oculus-christi on mammalian cell lines

    Directory of Open Access Journals (Sweden)

    Ralitsa K. Veleva

    2016-12-01

    Full Text Available Herbs of the genus Inula are well known in traditional medicine. Their extracts are used as expectorants, antitussives, bactericides as well as for the treatment of lung inflammation and have shown to possess anti-inflammatory and secretolytic activity. Experimental research findings indicate the anti-tumor effect of certain components of extracts from Inula cappa and Inula britannicа and those from Inula racemosa have antimicrobial and antidiabetic activity. We have directed our efforts on investigating the effects of different extracts from Inula oculus-christi, enriched with certain groups of biologically active substances - flavonoid glycosides (A, phenolic acids (B, flavonoid glycosides and phenolic acids (C, flavonoids and phenolic acids (D. The effect of these extracts on normal (MDCK ІІ and RPE1 and carcinoma cell lines (A549 and HepG2 was evaluated. We have performed cytotoxicity study (crystal violet assay as well as morphological analysis of changes induced by the extracts. Among the tumor cell lines HepG2 show greater sensitivity. Surprisingly extract C has no significant influence on both cancer cell lines.

  6. The Creation and Physiological Relevance of Divergent Hydroxylation Patterns in the Flavonoid Pathway

    Directory of Open Access Journals (Sweden)

    Heidi Halbwirth

    2010-02-01

    Full Text Available Flavonoids and biochemically-related chalcones are important secondary metabolites, which are ubiquitously present in plants and therefore also in human food. They fulfill a broad range of physiological functions in planta and there are numerous reports about their physiological relevance for humans. Flavonoids have in common a basic C6-C3-C6 skeleton structure consisting of two aromatic rings (A and B and a heterocyclic ring (C containing one oxygen atom, whereas chalcones, as the intermediates in the formation of flavonoids, have not yet established the heterocyclic C-ring. Flavonoids are grouped into eight different classes, according to the oxidative status of the C-ring. The large number of divergent chalcones and flavonoid structures is from the extensive modification of the basic molecules. The hydroxylation pattern influences physiological properties such as light absorption and antioxidative activity, which is the base for many beneficial health effects of flavonoids. In some cases antiinfective properties are also effected.

  7. Interaction of flavonoids, the naturally occurring antioxidants with different media: a UV-visible spectroscopic study.

    Science.gov (United States)

    Naseem, Bushra; Shah, S W H; Hasan, Aurangzeb; Sakhawat Shah, S

    2010-04-01

    Quantitative parameters for interaction of flavonoids-the naturally occurring antioxidants, with solvents and surfactants are determined using UV-visible absorption spectroscopy. The availability of flavonoids; kaempferol, apigenin, kaempferide and rhamnetin in micelles of sodium dodecyl sulfate (SDS) is reflected in terms of partition coefficient, K(c). Thermodynamic calculations show that the process of transfer of flavonoid molecules to anionic micelles of SDS is energy efficient. A distortion in flavonoid's morphology occurs in case of kaempferol and apigenin in surfactant and water, exhibited in terms of a new band in the UV region of electronic spectra of these flavonoids. The partition coefficients of structurally related flavonoids are correlated with their antioxidant activities. Copyright 2010 Elsevier B.V. All rights reserved.

  8. Extraction and determination of total flavonoids in jujube by alcohol extraction

    Science.gov (United States)

    Ji, Y. B.; Ru, X.; Yu, M.; Wang, S. W.; Lu, L.; Qiao, A. N.; Guo, A. Z.

    2017-12-01

    Jujube is a ripe fruit of Rhamnaceae. Its main active component is flavonoids, so the extraction and determination of total flavonoids in jujube will help to develop and utilize the medicinal value of jujube. In this study, the total flavonoids were extracted from jujube by alcohol extraction method. Through single factor investigation and orthogonal test, it was found that the total flavonoids content in jujube was the highest under the condition of 70°C, material ratio of 1:40, and extraction of 30 min by 70% ethanol. The content of total flavonoids in the extract of jujube was 1.57% at the wavelength of 510 nm by UV and rutin as the standard. The method was evaluated by methodological study, and it was determined that this method could be used as the detection of total flavonoids in jujube extraction.

  9. Study on the high flavonoids mutants of tartarian buckwheat by radiation induced mutation

    International Nuclear Information System (INIS)

    Li Guozhu; Shen Huifang

    2012-01-01

    Three different varieties of tartarian buckwheat seeds (Chuanqiao 1#, Yu-621 and KP9920) were irradiated with various doses (100∼500 Gy) of 60 Co-γ ray and sowed. Ten, eight and six high flavonoid tartary buckwheat mutants were selected from three parent materials respectively. The flavonoid content of three parent materials were 8.33%, 10.18% and 9.80%. The range of flavonoid content of high flavonoids mutants for three parent materials 11.37%∼14.91%, 10.67%∼12.46% and 11.32%∼12.95% respectively. Cluster analysis was also carried out based on the agronomic traits and flavonoid content in the 27 tartary buckwheat materials (24 mutants and 3 parent material) The 27 materials were classified into four clusters by cluster analysis based on the agronomic traits and were classified into 5 groups based on flavonoid content. (authors)

  10. [Determination of Flavonoids in Cycas revoluta Leaves by Chemiluminescence-Flow Injection Analysis Method].

    Science.gov (United States)

    Shi, Hong-yan; Zhu, Hai-ping; Qu, Ya-juan; Yang, Pei-jun

    2015-03-01

    To detect flavonoids from Cycas revoluta leaves by means of Chemiluminescence-Flow Injection Analysis (CL-FIA). Under alkaline condition, a CL-FIA method was established to determine flavonoids from leaves of Cycas revoluta on the basis of inhibiting effect of flavonoids to the Luminol-H2O2-Cu2+ chemiluminescence system and the reversed flow injection technique. In the range of 2. 0 x 10(-6) ~ 1. 0 x 10(-3) mg/mL, the decrease of CL intensity was correlated with flavonoids concentration while the detection limit was 0. 0265 µg/mL. Under the optimized conditions, the flavonoids of Cycas revoluta leaves were detected with its average rate reaching 1. 61% and RSD 1. 32%. Through the interference test and compared with the data of CL-FIA and UV, it is concluded that CL-FIA can be used in the analysis and detection of flavonoids from Cycas revoluta leaves.

  11. The influence of flavonoid amendment on the absorption of cadmium in Avicennia marina roots.

    Science.gov (United States)

    Li, Jian; Lu, Haoliang; Liu, Jingchun; Hong, Hualong; Yan, Chongling

    2015-10-01

    Flavonoid is a key factor for the tolerance to cadmium in plants. Concentration-dependent kinetics experiment was conducted to investigate the influence of flavonoid amendment on the Cd(2+) uptake in Avicennia marina (Forsk) Vierh. roots. We found that compared with the control, saturation concentration and maximal absorption rate of Cd was higher under flavonoid amendment (p<0.05). When roots were exposed to ion transport inhibitor (LaCl3), flavonoid amendment also facilitated Cd transport in roots. Flavonoids had no influence on Cd(2+) uptake in root cell walls. In conclusion, flavonoids enhance the tolerance to Cd and have a significant stimulative effect on symplasm transport of Cd in A. marina roots. Ca(2+)-channel was not the unique means of symplasm transport for Cd(2+) absorption. Copyright © 2015 Elsevier Inc. All rights reserved.

  12. Enhancement of Solubility and Antioxidant Activity of Some Flavonoids Based on the Inclusion Complexation with Sulfobutylether β-Cyclodextrin

    International Nuclear Information System (INIS)

    Kwon, Yong Eun; Kim, Hyun Myung; Jung, Seun Ho; Park, Se Yeon

    2010-01-01

    β-CD and SBE-β-CD functioned as a solubilizing agent against three flavonoids. SBE-β-CD is more efficient than native β-CD in solubility enhancement of tested flavonoids. All three tested flavonoids have antioxidant ability. Flavonoid-CD complex positively affected the antioxidant activity comparing with free flavonoids. Throughout this research, SBE-β-CD showed better complexation capacity for the solubility enhancement and bioavailability of tested flavonoids comparing with native β-CD. Flavonoids are polyphenolic photochemicals generally found in plants, foods, and beverages. They contribute to plant colors in fruit, leaves providing a wide spectrum of color from red to blue in flowers. Flavonoids have many good physiological activities such as the antioxidant, antitumor, and antibacterial activities which have been a focus of the attention of many researchers. There are four subgroups of flavonoids, flavone, flavonol, flavanone, and isoflavone, according to their chemical structure

  13. Quantitative Structure – Antioxidant Activity Relationships of Flavonoid Compounds

    Directory of Open Access Journals (Sweden)

    Károly Héberger

    2004-12-01

    Full Text Available A quantitative structure – antioxidant activity relationship (QSAR study of 36 flavonoids was performed using the partial least squares projection of latent structures (PLS method. The chemical structures of the flavonoids have been characterized by constitutional descriptors, two-dimensional topological and connectivity indices. Our PLS model gave a proper description and a suitable prediction of the antioxidant activities of a diverse set of flavonoids having clustering tendency.

  14. Isolation and Identification of Flavonoid in Katu Leaf (Sauropus androgynus (L. Merr

    Directory of Open Access Journals (Sweden)

    Sri Harsodjo Wijono

    2003-08-01

    Full Text Available lavonoids in 95% ethanol extract of katu leaf were isolated using Charaux-Paris method. Extract of 95 % ethanol was fractionated with chloroform, ethyl acetate and three times with n-butanol. Flavonoids to be isolated from n-butanol I fraction by chromatography paper preparative method, and identified by spectrophotometer UV (Ultra-Violet and infrared. Six flavonoids were isolated, one of flavonoids identified as rutin, and the other five were flavonol OH-3 conjugated or flavon groups.

  15. Intake of dietary flavonoids and risk of epithelial ovarian cancer 1 2 3 4

    OpenAIRE

    Cassidy, Aedín; Huang, Tianyi; Rice, Megan S; Rimm, Eric B; Tworoger, Shelley S

    2014-01-01

    Background: The impact of different dietary flavonoid subclasses on risk of epithelial ovarian cancer is unclear, with limited previous studies that have focused on only a few compounds. Objective: We prospectively examined associations between habitual flavonoid subclass intake and risk of ovarian cancer. Design: We followed 171,940 Nurses’ Health Study and Nurses’ Health Study II participants to examine associations between intakes of total flavonoids and their subclasses (flavanones, flavo...

  16. Intake of dietary flavonoids and risk of epithelial ovarian cancer1234

    OpenAIRE

    Cassidy, Aedín; Huang, Tianyi; Rice, Megan S; Rimm, Eric B; Tworoger, Shelley S

    2014-01-01

    Background: The impact of different dietary flavonoid subclasses on risk of epithelial ovarian cancer is unclear, with limited previous studies that have focused on only a few compounds. Objective: We prospectively examined associations between habitual flavonoid subclass intake and risk of ovarian cancer. Design: We followed 171,940 Nurses’ Health Study and Nurses’ Health Study II participants to examine associations between intakes of total flavonoids and their subclasses (flavanones, flavo...

  17. Flavonoids function as antioxidants: by scavenging reactive oxygen species or by chelating iron?

    Energy Technology Data Exchange (ETDEWEB)

    Wuguo Deng; Xingwang Fang; Jilan Wu [Peking Univ., Technical Physics Dept., Beijing (China)

    1997-09-01

    Flavonoids have been reported to exhibit strong antioxidative activity. In the present work, a systematic mechanistic study has been performed on five flavonoids (baicalin, hesperidin, naringin, quercetin and rutin) selected according to their structural characteristics. The experimental results reveal that flavonoids function as antioxidant mainly by chelating iron ions and by scavenging peroxyl radicals whereas their OH radical scavenging effect is much less important. (author).

  18. The role of metabolism (and the microbiome) in defining the clinical efficacy of dietary flavonoids1

    Science.gov (United States)

    Cassidy, Aedín; Minihane, Anne-Marie

    2017-01-01

    At a population level, there is growing evidence of the beneficial effects of dietary flavonoids on health. However, there is extensive heterogeneity in the response to increased intake, which is likely mediated via wide interindividual variability in flavonoid absorption and metabolism. Flavonoids are extensively metabolized by phase I and phase II metabolism (which occur predominantly in the gastrointestinal tract and liver) and colonic microbial metabolism. A number of factors, including age, sex, and genotype, may affect these metabolic processes. In addition, food composition and flavonoid source are likely to affect bioavailability, and emerging data suggest a critical role for the microbiome. This review will focus on the current knowledge for the main subclasses of flavonoids, including anthocyanins, flavonols, flavan-3-ols, and flavanones, for which there is growing evidence from prospective studies of beneficial effects on health. The identification of key factors that govern metabolism and an understanding of how the differential capacity to metabolize these bioactive compounds affect health outcomes will help establish how to optimize intakes of flavonoids for health benefits and in specific subgroups. We identify research areas that need to be addressed to further understand important determinants of flavonoid bioavailability and metabolism and to advance the knowledge base that is required to move toward the development of dietary guidelines and recommendations for flavonoids and flavonoid-rich foods. PMID:27881391

  19. Antioxidant Activities and Chemical Constituents of Flavonoids from the Flower of Paeonia ostii.

    Science.gov (United States)

    Zhang, Huifang; Li, Xiaofang; Wu, Ke; Wang, Mengke; Liu, Pu; Wang, Xinsheng; Deng, Ruixue

    2016-12-23

    Paeonia ostii is a traditional medicinal plant popularly used in China. This study intended to evaluate the antioxidant properties and the chemical components of the flavonoid-rich extracts from the flowers of P. ostii . The results showed that the flavonoid-rich extracts from the flowers of P. ostii had strong scavenging capacities on 2,2'-Azinobis-(3-ethylbenzthiazoline-6-sulphonate) (ABTS), hydroxyls, superoxide anions, and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals in a dose-dependent manner. Five flavonoids, dihydrokaempferol ( 1 ), apigenin-7- O -β-d-glucoside ( 2 ), apigenin-7- O -β-d-neohesperidoside ( 3 ), kaempferol-7- O -β-d-glucopyranoside ( 4 ), and kaempferol-3- O -β-d-glucopyranosyl-7- O -β-d-glucopyranoside ( 5 ), were isolated from the flavonoid-rich extracts of the flowers of P. ostii . High-performance liquid chromatography (HPLC) analysis revealed that compounds 3 and 4 were abundant in the P. ostii flower and in flavonoid-rich extracts. The main components of the flower of P. ostii are flavonoids. The high antioxidant activity of the flavonoid-rich extracts may be attributed to the high content of flavonoids. The five isolated flavonoids were the primary antioxidant ingredients, and may play important roles in the strong antioxidant activities of this flower. Based on the obtained results, the flower of P. ostii could be a potential source of natural antioxidants in food and pharmaceutical applications.

  20. Preparative Separation and Purification of the Total Flavonoids in Scorzonera austriaca with Macroporous Resins.

    Science.gov (United States)

    Xie, Yang; Guo, Qiu-Shi; Wang, Guang-Shu

    2016-06-13

    The use of macroporous resins for the separation and purification of total flavonoids to obtain high-purity total flavonoids from Scorzonera austriaca was studied. The optimal conditions for separation and purification of total flavonoids in S. austriaca with macroporous resins were as follows: D4020 resin columns were loaded with crude flavonoid extract solution, and after reaching adsorptive saturation, the columns were eluted successively with 5 bed volumes (BV) of water, 5 BV of 5% (v/v) aqueous ethanol and 5 BV of 30% (v/v) aqueous ethanol at an elute flow rate of 2 BV·h(-1). Total flavonoids were obtained from the 30% aqueous ethanol eluate by vacuum distillation recovery. The content of flavonoid compounds in the total flavonoids was 93.5%, which represents an improvement by about 150%. In addition, five flavonoid compounds in the product were identified as 2″-O-β-d-xylopyranosyl isoorientin, 6-C-α-l-arabipyranosyl orientin, orientin, isoorientin and vitexin by LC-ESI-MS analysis and internal standard methods. The results in this study could represent a method for the large-scale production of total flavonoids from S. austriaca.

  1. Effect of room temperature ionic liquid structure on the enzymatic acylation of flavonoids

    DEFF Research Database (Denmark)

    Lue, Bena-Marie; Guo, Zheng; Xu, Xuebing

    2010-01-01

    Enzymatic acylation reactions of flavonoids (rutin, esculin) with long chain fatty acids (palmitic, oleic acids) were carried out in 14 different ionic liquid media containing a range of cation and anion structures. Classification of RTILs according to flavonoid solubility (using COSMO...... must be struck that maximized flavonoid solubility with minimum negative impact on lipase activity. The process also benefitted from an increased reaction temperature which may have helped to reduced mass transfer limitations. Keywords: Room temperature ionic liquids (RTILs); Biosynthesis; Acylation......; Flavonoids; Lipase; Long chain fatty acids...

  2. The role of metabolism (and the microbiome) in defining the clinical efficacy of dietary flavonoids.

    Science.gov (United States)

    Cassidy, Aedín; Minihane, Anne-Marie

    2017-01-01

    At a population level, there is growing evidence of the beneficial effects of dietary flavonoids on health. However, there is extensive heterogeneity in the response to increased intake, which is likely mediated via wide interindividual variability in flavonoid absorption and metabolism. Flavonoids are extensively metabolized by phase I and phase II metabolism (which occur predominantly in the gastrointestinal tract and liver) and colonic microbial metabolism. A number of factors, including age, sex, and genotype, may affect these metabolic processes. In addition, food composition and flavonoid source are likely to affect bioavailability, and emerging data suggest a critical role for the microbiome. This review will focus on the current knowledge for the main subclasses of flavonoids, including anthocyanins, flavonols, flavan-3-ols, and flavanones, for which there is growing evidence from prospective studies of beneficial effects on health. The identification of key factors that govern metabolism and an understanding of how the differential capacity to metabolize these bioactive compounds affect health outcomes will help establish how to optimize intakes of flavonoids for health benefits and in specific subgroups. We identify research areas that need to be addressed to further understand important determinants of flavonoid bioavailability and metabolism and to advance the knowledge base that is required to move toward the development of dietary guidelines and recommendations for flavonoids and flavonoid-rich foods.

  3. [Use of chromatospectrometric methods for quantitative evaluation of flavonoids in complex tablets].

    Science.gov (United States)

    Tsomaia, I

    2013-03-01

    In the article are shown the results of quantitative evaluation of Flavonoids using Chromatospectrophotometric method, based on color reaction with aluminium chloride. The optimized conditions of Flavonoid's extraction from complex tablets were developed: the right substance, time and temperature for extraction were selected, accordingly - alcohol of 95%, 90 min time and the room temperature. The selected Chromatospectrophotometric method makes possible the accurate evaluation of the content of Flavonoids in complex tablets. Relative error of measurement in the state of confidence probability equal to 95 doesn't exceed ± 5,0%. The margines for content of Flavonoids in one tablet were defined as 20 to 50 mg.

  4. Free radical scavenging activity of Eagle tea and their flavonoids

    Directory of Open Access Journals (Sweden)

    Qiong Meng

    2012-06-01

    Full Text Available In this study, an online HPLC-DAD-MS coupled with 2,2′-azinobis (3-ethylbenzthiazoline-6-sulfonic acid diammonium salt (ABTS assay was employed for evaluating free radical scavenging activity of Eagle tea and their active components. Twenty-three chromatographic peaks were detected, and nineteen components had free radical scavenging activity. Among them, eight compounds were identified as flavonoids (hyperin, isoquercitrin, quercitrin, quercetin, kaempferol, catechins, chlorogenic acid and epicatechin based on MS data and standard chromatographic characters.

  5. Bioavailability, metabolism and potential health protective effects of dietary flavonoids

    DEFF Research Database (Denmark)

    Bredsdorff, Lea

    biological samples and food frequency questionnaires (FFQs) from 57 053 cohort members. Higher urinary excretion of kaempferol was statistically significant associated with a consistent 44-60 % lower risk of ACS. The lower risk associated with urinary kaempferol excretion was probably attributable to tea...... that the study was too limited in size to account for the variation associated with quantifying flavonoids in spot-urine samples. However, the non-monotonic, but statistically significant, association between higher kaempferol excretion and lower risk of ACS indicate that the lack of associations were not due...

  6. 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...... biosynthetic pathways, comprising up to eight heterologous genes from plants. The obtained titers of kaempferol 26.57±2.66mgL-1 and quercetin 20.38±2.57mgL-1 exceed the previously reported titers in yeast. This is also the first report of de novo biosynthesis of resokaempferol and fisetin in yeast. The work...

  7. Flavonoid Glycosides from the Leaves of Cissus Ibuensis Hook (Vitaceae)

    OpenAIRE

    Ahmadu, AA; Onanuga, A; Aquino, R

    2010-01-01

    The bioactive N-butanol fraction of the ethanol extract of the leaves of Cissus ibuensis was fractionated over silica Gel column to give Quercetin 3-O-rutinoside (I) and mixtures of Flavonoids (A2). A2 was fractionated using reverse phase HPLC to give Kaempferol 3-O-α-rhamnopyranosyl (1→6)-β;-D-galactopyranoside (II), Kaempferol 3-O-rutinoside(III)and Kaempferol3-O-α-rhamnopyranosyl (1→6)-α-rhamnopyranosyl(1→2)-β;-D-galactopyranoside (IV). The structures were elucidated by NMR spectroscopy an...

  8. Flavonoid glycosides from the leaves of Cissus ibuensis hook (vitaceae).

    Science.gov (United States)

    Ahmadu, A A; Onanuga, A; Aquino, R

    2010-04-03

    The bioactive N-butanol fraction of the ethanol extract of the leaves of Cissus ibuensis was fractionated over silica Gel column to give Quercetin 3-O-rutinoside (I) and mixtures of Flavonoids (A2). A2 was fractionated using reverse phase HPLC to give Kaempferol 3-O-α-rhamnopyranosyl (1→6)-β-D-galactopyranoside (II), Kaempferol 3-O-rutinoside(III) and Kaempferol3-O-α-rhamnopyranosyl (1→6)-α-rhamnopyranosyl(1→2)-β-D-galactopyranoside (IV). The structures were elucidated by NMR spectroscopy and compared with literature.

  9. Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae)

    OpenAIRE

    Pereira, Cristiane; Barreto Júnior, Cleber Bomfim; Kuster, Ricardo Machado; Simas, Naomi Kato; Sakuragui, Cassia Mônica; Porzel, Andrea; Wessjohann, Ludger

    2012-01-01

    This work describes the phytochemical study of the methanol extract obtained from leaves of Guarea macrophylla, leading to the isolation and identification of three flavonoid glycosides (quercetin 3-O-β-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-β-D-glucopyranoside) and a neolignan glucoside, dehydrodiconiferyl alcohol-4-β-D-glucoside. All compounds were identified by a combination of spectroscopic methods (¹H, 1D, 2D NMR, 13C and UV), ESI-MS and com...

  10. Flavonoid Compounds from the Bark of Aglaia eximia (Meliaceae)

    OpenAIRE

    Julinton Sianturi; Mayshah Purnamasari; Tri Mayanti; Desi Harneti; Unang Supratman; Khalijah Awang; Hideo Hayashi

    2015-01-01

    Three flavonoid compounds, kaempferol (1), kaempferol-3-O-α-L-rhamnoside (2), and kaempferol-3-O-β-D-glucosyl-α-L-rhamnoside (3), were isolated from the bark of Aglaia eximia (Meliaceae). The chemical structures of compounds 1–3 were identified with spectroscopic data, including UV, IR, NMR (1H, 13C, DEPT 135°, HMQC, HMBC, 1H-1H-COSY NMR), and MS, as well as a compared with previously reported spectra data. All compounds were evaluated for their cytotoxic effects against P-388 murine leukemia...

  11. [Studying the mechanism of antioxidant effect of vitamins and flavonoids].

    Science.gov (United States)

    Makarov, V G; Makarova, M N; Selezneva, A I

    2005-01-01

    In work antiradical activity of vitamins and flafonoids in relation to hydroxyl radical is established. The most antiradical activity is established for flavonoids quercetin, routin, daidzein, biochanin A and luteolin-7glucosid, Among vitamins of group in the most antiradical activity have shown vitamins B12, B2, B5, Bc. In group of fat-soluble vitamins ascorbic palmitat, vitamin K1, vitamin A and beta-carotin have shown activity above, than a known antioxidant vitamin E. The carried out work allows to draw a conclusion that antiradical activity in the relation hydroxyl radical shows the broad audience of vitamins that probably is one of aspects of their therapeutic action.

  12. A New Flavonoid Glycoside from Salix denticulata Aerial Parts

    Directory of Open Access Journals (Sweden)

    Amita Bamola

    2009-09-01

    Full Text Available Abstract: A new flavonoid glycoside (1 has been isolated from the aerial parts of Salix denticulata (Salicaceae together with five known compounds, β-sitosterol, 2,6-dihydroxy- 4-methoxy acetophenone, eugenol-1-O-β-D-glucopyranoside, 1-O-β-D-(3’-benzoyl salicyl alcohol and luteolin-7-O-β-D-glucopyranosyl-(1-6-glucopyranoside. The structure of 1 was elucidated as 2’,5-dihydroxy-3’-methoxyflavone-7-O-β-D-glucopyranoside by means of chemical and spectral data including 2D NMR studies.

  13. A Novel Flavonoid Glucoside from the Fruits of Lycium ruthenicun

    Directory of Open Access Journals (Sweden)

    Jing-Jing Qi

    2018-02-01

    Full Text Available A novel flavonoid glucoside, ruthenicunoid A (1, together with eight known substances, were isolated from the fruits of Lycium ruthenicun Murr. Their structures were elucidated by extensive spectroscopic data and chemical methods. Especially, the absolute configuration of glucose residue in 1 was assigned by acid hydrolysis followed by derivatization and GC analysis. Biological evaluation towards Sirtuin 1 (SIRT1 found that compounds 1 and 2 exhibit inhibitory activity against SIRT1 in a concentration-dependent manner, indicating its potential on SIRT1-associated disorders.

  14. Optimizing extraction conditions of crude fiber, phenolic compounds, flavonoids and antioxidant activity of date seed powder.

    Science.gov (United States)

    Afifi, Hanan S; Hashim, Isameldin B; Altubji, Sabreen I

    2017-12-01

    The objective of this study was to optimize the extraction conditions of crude fiber, phenolic compounds, flavonoids, and antioxidant activity from date seeds powder, using Response Surface Methodology. A central composite design with four independent variables; concentration of ethanol (X 1  = 25, 50 and 75% v/v), solvent: sample ratio (X 2  = 40:1, 50:1 and 60:1 v/w), temperature (X 3  = 45, 55 and 65 °C), and extraction time (X 4  = 1, 2 and 3 h) and a three level face centered cube design were used. A total of twenty nine experimental runs with five replicates at the central point were used to study the response variables using two extraction cycles. Maximum phenolic compound content (71.6 mg GAE/100 g) was extracted using 50% ethanol solution with 40:1 solvent: sample ratio for 1 h at 55 °C. While the maximum antioxidant activity (55.02 µmol Fe(II)/g) was obtained using similar ethanol concentration and solvent: sample ratio except at lower temperature (45 °C) for 2 h. On other hand, the maximum flavonoids content (455.77 mg CEQ/100 g) was reached by using 50% concentration, 50:1 solvent: sample ratio at 65 °C for 3 h. In contrast, the content of fiber was not affected by the different extraction conditions. Results indicate that using combination of extracted conditions, have a great potential for extracting all depending compounds except crude fiber.

  15. Study of the interaction of flavonoids with 3-mercaptopropionic acid modified CdTe quantum dots mediated by cetyltrimethyl ammonium bromide in aqueous medium

    Science.gov (United States)

    Aucelio, Ricardo Q.; Carvalho, Juliana M.; Real, Juliana T.; Maqueira-Espinosa, Luis; Pérez-Gramatges, Aurora; da Silva, Andrea R.

    2017-02-01

    Flavonoids are polyphenols that help the maintenance of health, aiding the prevention of diseases. In this work, CdTe QDs coated with 3-mercaptopropionic acid (3MPA), with an average size of 2.7 nm, were used as photoluminescence probe for flavonoids in different conditions. The interaction between 14 flavonoids and QDs was evaluated in aqueous dispersions in the absence and in the presence of cetyltrimethylammonium bromide (CTAB). To establish a relationship between photoluminescence quenching and the concentration of flavonoids, the Stern-Volmer model was used. In the absence of CTAB, the linear ranges for quercetin, morin and rutin were from 5.0 × 10- 6 mol L- 1 to 6.0 × 10- 5 mol L- 1 and from 1.0 × 10- 5 mol L- 1 to 6.0 × 10- 4 mol L- 1 for kaempferol. The sensibility of the Stern-Volmer curves (Ks) indicated that quercetin interacts more strongly with the probe: Ks quercetin > Ks kaempferol > Ks rutin > Ks morin. The conjugation extension in the 3 rings, and the acidic hydroxyl groups (positions 3ʹand 4ʹ) in the B-ring enhanced the interaction with 3MPA-CdTe QDs. The other flavonoids do not interact with the probe at 10- 5 mol L- 1 level. In CTAB organized dispersions, Ks 3-hydroxyflavone > Ks 7-hydroxyflavone > Ks flavona > Ks rutin in the range from 1.0 × 10- 6 mol L- 1 to 1.2 × 10- 5 mol L- 1 for flavones and of 1.0 × 10- 6 mol L- 1 to 1.0 × 10- 5 mol L- 1 for rutin. Dynamic light scattering, conductometric measurements and microenvironment polarity studies were employed to elucidate the QDs-flavonoids interaction in systems containing CTAB. The quenching can be attributed to the preferential solubility of hydrophobic flavonoid in the palisade layer of the CTAB aggregates adsorbed on the surface of the 3MPA CdTe QDs.

  16. Estimation of dietary flavonoid intake and major food sources of Korean adults.

    Science.gov (United States)

    Jun, Shinyoung; Shin, Sangah; Joung, Hyojee

    2016-02-14

    Epidemiological studies have suggested that flavonoids exhibit preventive effects on degenerative diseases. However, lack of sufficient data on flavonoid intake has limited evaluating the proposed effects in populations. Therefore, we aimed to estimate the total and individual flavonoid intakes among Korean adults and determine the major dietary sources of these flavonoids. We constructed a flavonoid database of common Korean foods, based on the food list reported in the 24-h recall of the Korea National Health and Nutrition Examination Survey (KNHANES) 2007-2012, using data from the Korea Functional Food Composition Table, US Department of Agriculture flavonoid database, Phenol-Explorer database and other analytical studies. This database, which covers 49 % of food items and 76 % of food intake, was linked with the 24-h recall data of 33 581 subjects aged ≥19 years in the KNHANES 2007-2012. The mean daily intake of total flavonoids in Korean adults was 318·0 mg/d, from proanthocyanidins (22·3%), flavonols (20·3%), isoflavones (18·1%), flavan-3-ols (16·2%), anthocyanidins (11·6%), flavanones (11·3%) and flavones (0·3%). The major contributing food groups to the flavonoid intake were fruits (54·4%), vegetables (20·5%), legumes and legume products (16·2%) and beverages and alcohols (3·1%), and the major contributing food items were apples (21·9%), mandarins (12·5%), tofu (11·5%), onions (9·6%) and grapes (9·0%). In the regression analysis, the consumption of legumes and legume products, vegetables and fruits predicted total flavonoid intake the most. The findings of this study could facilitate further investigation on the health benefits of flavonoids and provide the basic information for establishing recommended flavonoid intakes for Koreans.

  17. Neurodegenerative Diseases: Might Citrus Flavonoids Play a Protective Role?

    Directory of Open Access Journals (Sweden)

    Santa Cirmi

    2016-09-01

    Full Text Available Neurodegenerative diseases (ND result from the gradual and progressive degeneration of the structure and function of the central nervous system or the peripheral nervous system or both. They are characterized by deterioration of neurons and/or myelin sheath, disruption of sensory information transmission and loss of movement control. There is no effective treatment for ND, and the drugs currently marketed are symptom-oriented, albeit with several side effects. Within the past decades, several natural remedies have gained attention as potential neuroprotective drugs. Moreover, an increasing number of studies have suggested that dietary intake of vegetables and fruits can prevent or delay the onset of ND. These properties are mainly due to the presence of polyphenols, an important group of phytochemicals that are abundantly present in fruits, vegetables, cereals and beverages. The main class of polyphenols is flavonoids, abundant in Citrus fruits. Our review is an overview on the scientific literature concerning the neuroprotective effects of the Citrus flavonoids in the prevention or treatment of ND. This review may be used as scientific basis for the development of nutraceuticals, food supplements or complementary and alternative drugs to maintain and improve the neurophysiological status.

  18. Recent Advances and Uses of Grape Flavonoids as Nutraceuticals

    Science.gov (United States)

    Georgiev, Vasil; Ananga, Anthony; Tsolova, Violeta

    2014-01-01

    Grape is one of the oldest fruit crops domesticated by humans. The numerous uses of grape in making wine, beverages, jelly, and other products, has made it one of the most economically important plants worldwide. The complex phytochemistry of the berry is characterized by a wide variety of compounds, most of which have been demonstrated to have therapeutic or health promoting properties. Among them, flavonoids are the most abundant and widely studied, and have enjoyed greater attention among grape researchers in the last century. Recent studies have shown that the beneficial health effects promoted by consumption of grape and grape products are attributed to the unique mix of polyphenolic compounds. As the largest group of grape polyphenols, flavonoids are the main candidates considered to have biological properties, including but not limited to antioxidant, anti-inflammatory, anti-cancer, antimicrobial, antiviral, cardioprotective, neuroprotective, and hepatoprotective activities. Here, we discuss the recent scientific advances supporting the beneficial health qualities of grape and grape-derived products, mechanisms of their biological activity, bioavailability, and their uses as nutraceuticals. The advantages of modern plant cell based biotechnology as an alternative method for production of grape nutraceuticals and improvement of their health qualities are also discussed. PMID:24451310

  19. Plantain (Plantago L.) species as novel sources of flavonoid antioxidants.

    Science.gov (United States)

    Beara, Ivana N; Lesjak, Marija M; Jovin, Emilija D; Balog, Kristina J; Anackov, Goran T; Orcić, Dejan Z; Mimica-Dukić, Neda M

    2009-10-14

    To examine the antioxidant properties of methanol extracts of selected Plantago species (P. argentea Chaix., P. holosteum Scop., P. major L., P. maritima L., and P. media L.), various assays that measure free radical scavenging ability were carried out: DPPH, hydroxyl radical, superoxide anion, and nitric oxide scavenger capacity tests, reducing power (FRAP) assay, and Fe(2+)/ascorbate induced lipid peroxidation. In all of the tests extracts showed a potent antioxidant effect compared with BHT, a well-known synthetic antioxidant, and the extract of P. major, accepted as an official remedy. Besides, in examined extracts the total phenolic amount (ranging from 38.43 to 70.97 mg of GAE/g of dw) and the total flavonoid content (5.31-13.10 mg of QE/g of dw) were determined. Furthermore, the presence and content of selected flavonoids (luteolin-7-O-glucoside, apigenin-7-O-glucoside, luteolin, apigenin, rutin, and quercetin) were studied using LC-MS/MS technique. LC-MS/MS analysis showed noticeable qualitative and quantitative differences between the species according to which the examined Plantago species could be regarded as a possible new source of natural antioxidants. In this study three of the species examined, P. maritima, P. argentea, and P. holosteum, have been analyzed for the first time.

  20. A new bioactive monoterpene-flavonoid from Satureja khuzistanica.

    Science.gov (United States)

    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.

  1. Analysis of Arabidopsis mutants deficient in flavonoid biosynthesis

    International Nuclear Information System (INIS)

    Shirley, B.W.; Kubasek, W.L.; Storz, G.; Bruggemann, E.; Koornneef, M.; Ausubel, F.M.; Goodman, H.M.

    1995-01-01

    Eleven loci that play a role in the synthesis of flavonoids in Arabidopsis are described. Mutations at these loci, collectively named transparent testa (tt), disrupt the synthesis of brown pigments in the seed coat (testa). Several of these loci (tt3, tt4, tt5 and ttg) are also required for the accumulation of purple anthocyanins in leaves and stems and one locus (ttg) plays additional roles in trichome and root hair development. Specific functions were previously assigned to tt1-7 and ttg. Here, the results of additional genetic, biochemical and molecular analyses of these mutants are described. Genetic map positions were determined for tt8, tt9 and tt10. Thin-layer chromatography identified tissue- and locus-specific differences in the flavonols and anthocyanidins synthesized by mutant and wild-type plants. It was found that UV light reveals distinct differences in the floral tissues of tt3, tt4, tt5, tt6 and ttg, even though these tissues are indistinguishable under visible light. Evidence was also uncovered that tt8 and ttg specifically affect dihydroflavonol reductase gene expression. A summary of these and previously published results are incorporated into an overview of the genetics of flavonoid biosynthesis in Arabidopsis

  2. Recent Advances and Uses of Grape Flavonoids as Nutraceuticals

    Directory of Open Access Journals (Sweden)

    Vasil Georgiev

    2014-01-01

    Full Text Available Grape is one of the oldest fruit crops domesticated by humans. The numerous uses of grape in making wine, beverages, jelly, and other products, has made it one of the most economically important plants worldwide. The complex phytochemistry of the berry is characterized by a wide variety of compounds, most of which have been demonstrated to have therapeutic or health promoting properties. Among them, flavonoids are the most abundant and widely studied, and have enjoyed greater attention among grape researchers in the last century. Recent studies have shown that the beneficial health effects promoted by consumption of grape and grape products are attributed to the unique mix of polyphenolic compounds. As the largest group of grape polyphenols, flavonoids are the main candidates considered to have biological properties, including but not limited to antioxidant, anti-inflammatory, anti-cancer, antimicrobial, antiviral, cardioprotective, neuroprotective, and hepatoprotective activities. Here, we discuss the recent scientific advances supporting the beneficial health qualities of grape and grape-derived products, mechanisms of their biological activity, bioavailability, and their uses as nutraceuticals. The advantages of modern plant cell based biotechnology as an alternative method for production of grape nutraceuticals and improvement of their health qualities are also discussed.

  3. A COMPARATIVE STUDY OF BACTERIOSTATIC ACTIVITY OF SYNTHETIC HYDROXYLATED FLAVONOIDS

    Directory of Open Access Journals (Sweden)

    Olivella Mónica S.

    2001-01-01

    Full Text Available Among other properties, flavonoids present a notable bacteriostatic activity. In this paper, minimal inhibitory concentrations (MICs of 5,7,4'-trihydroxyflavanone (naringenin, 5,7-dihydroxyflavone and 2',4',4- trihydroxychalcone (isoliquitirigenin against Staphylococcus aureus ATCC 25 923 were determined and compared to values obtained for other chalcones and flavanones previously investigated. Specific growth rates and MICs were determined by a turbidimetric kinetic method. The observed sequence MICflavanone (inactive >MIC7-hidroxyflavanone (197.6 µgml-1>MIC5,7,4'-trihydroxyflavanone (120 µgml-1 showed that the introduction of an electron donating group (-OH causes an increase in bioactivity. On the other hand, the comparisons MIC5,7,4'-trihydroxyflavanone (120 µgml-1 >>> MIC2',4',4-trihydroxychalcone (29 µgml-1 and MIC5,7-dihydroxyflavone (105 µgml-1 >>> MIC2',4'-dihydroxychalcone (28.8 µgml-1 indicated that the chalcone structure is the most favourable for bacteriostatic activity within the flavonoid family.

  4. Antioxidant and Antiradical Properties of Selected Flavonoids and Phenolic Compounds

    Directory of Open Access Journals (Sweden)

    Zübeyir Huyut

    2017-01-01

    Full Text Available Phenolic compounds and flavonoids are known by their antioxidant properties and one of the most important sources for humans is the diet. Due to the harmful effects of synthetic antioxidants such as BHA and BHT, natural novel antioxidants have become the focus of attention for protecting foods and beverages and reducing oxidative stress in vivo. In the current study, we investigated the total antioxidant, metal chelating, Fe3+ and Cu2+ reduction, and free radical scavenging activities of some phenolic and flavonoid compounds including malvin, oenin, ID-8, silychristin, callistephin, pelargonin, 3,4-dihydroxy-5-methoxybenzoic acid, 2,4,6-trihydroxybenzaldehyde, and arachidonoyl dopamine. The antioxidant properties of these compounds at different concentrations (10–30 μg/mL were compared with those of reference antioxidants such as BHA, BHT, α-tocopherol, and trolox. Each substance showed dose-dependent antioxidant activity. Furthermore, oenin, malvin, arachidonoyl dopamine, callistephin, silychristin, and 3,4-dihydroxy-5-methoxybenzoic acid exhibited more effective antioxidant activity than that observed for the reference antioxidants. These results suggest that these novel compounds may function to protect foods and medicines and to reduce oxidative stress in vivo.

  5. Antimicrobial activity screening of isolated flavonoids from Azadirachta indica leaves

    Directory of Open Access Journals (Sweden)

    QUDSIA KANWAL

    2011-03-01

    Full Text Available The antimicrobial activities of two flavonoids, namely genistein 7-O-glucoside (1 and (–-epi-catechin (2, isolated from Azadirachta indica A. Juss (neem leaves, were evaluated against five fungal species, viz: Alternaria alternata (Fr. Keissler, Aspergillus fumigatus Fresenius, Aspergillus niger van Tieghem, Macrophomina phaseolina (Tassi Goid. and Penicillium citrii, and four bacterial species, viz. Lactobacillus sp., Escherichia coli, Azospirillium lipoferum and Bacillus sp. Six concentrations, viz. 100, 300, 500, 700, 900 and 1000 ppm of each of the two flavonoids were employed using malt extract agar medium. All the concentrations of both the test compounds significantly suppressed fungal as well as bacterial growth. The highest concentration (1000 ppm of both fractions 1 and 2 reduced the growth of the different test fungal species by 83–99 % and 82–95 %, respectively. Compound 1 was highly effective against Lactobacillus sp., against which its various concentrations reduced the bacterial growth by 52–99.8 %. Compound 2 was highly effective against A. lipoferum and Bacillus sp., resulting in 94–100 % and 73–99% reduction in bacterial growth, respectively.

  6. Inhibition of 2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) Formation by Alkoxy Radical Scavenging of Flavonoids and Their Quantitative Structure-Activity Relationship in a Model System.

    Science.gov (United States)

    Yu, Chundi; Shao, Zeping; Liu, Bing; Zhang, Yan; Wang, Shuo

    2016-08-01

    The inhibitory effect of 10 flavonoids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in a creatinine-phenylalanine model system was investigated through electronic spin resonance and a quantitative structure-activity relationship. Alkoxy radicals were observed during the heating process, providing evidence for a radical pathway in the formation of PhIP. The alkoxy radical scavenging capability of the flavonoids was proportional to their inhibition of PhIP formation (IC50 ). We deduced that flavonoid inhibition of PhIP generation occurs via scavenging of alkoxy radicals during the heating process. Multiple linear regression and partial least squares models were used to elucidate the relationship between PhIP inhibition activity and structure characteristics of the flavonoids. The lipo-hydro partition coefficient and molecular fractional polar surface area of the flavonoids were found to be predictive of the inhibition effect. © 2016 Institute of Food Technologists®

  7. Metabolic engineering of flavonoids in tomato (Solanum lycopersicum): the potential for metabolomics

    NARCIS (Netherlands)

    Bovy, A.G.; Schijlen, E.G.W.M.; Hall, R.D.

    2007-01-01

    Flavonoids comprise a large and diverse group of polyphenolic plant secondary metabolites. In plants, flavonoids play important roles in many biological processes such as pigmentation of flowers, fruits and vegetables, plant-pathogen interactions, fertility and protection against UV light. Being

  8. Pathway engineering for healthy phytochemicals leading to the production of novel flavonoids in tomato fruit

    NARCIS (Netherlands)

    Schijlen, E.G.W.M.; Vos, de C.H.; Jonker, H.H.; Broeck, van den H.C.; Molthoff, J.W.; Tunen, van A.J.; Martens, S.; Bovy, A.G.

    2006-01-01

    Flavonoids are a large family of plant polyphenolic secondary metabolites. Although they are widespread throughout the plant kingdom, some flavonoid classes are specific for only a few plant species. Due to their presumed health benefits there is growing interest in the development of food crops

  9. Unravelling mechanisms of dietary flavonoid-mediated health effects: effects on lipid metabolism and genotoxicity

    NARCIS (Netherlands)

    Hoek-van den Hil, E.F.

    2015-01-01

    Summary Consumption of foods containing flavonoids is associated with a reduced risk of cardiovascular diseases (CVD), possibly by lipid-lowering effects. On the other hand, for one of these flavonoids, quercetin, also genotoxicity was shown especially in in vitro bioassays.

  10. Synergistic inhibition of glycinergic transmission in vitro and in vivo by flavonoids and strychnine.

    Science.gov (United States)

    Raafat, Karim; Breitinger, Ulrike; Mahran, Laila; Ayoub, Nahla; Breitinger, Hans-Georg

    2010-11-01

    The inhibitory glycine receptor (GlyR) is a key mediator of synaptic signaling in spinal cord, brain stem, and higher central nervous system regions. The flavonoids quercetin and genistein have been identified previously as promising GlyR antagonists in vitro, but their detailed mechanism of action was not known. Here, inhibition of recombinant human α1 GlyRs in HEK 293 cells by genistein, quercetin, and strychnine was studied using whole-cell recording techniques. The interaction of several inhibitors applied alone or in combination was analyzed using a minimum mechanism of receptor activation and inhibition. Receptor inhibition in vivo was studied in a mouse model of strychnine toxicity. Genistein, quercetin, and strychnine were noncompetitive GlyR inhibitors. The inhibitory potency of one flavonoid (either genistein or quercetin) was not affected by simultaneous application of the other, suggesting that both flavonoids target the same site on the receptor. In combination with strychnine, flavonoid inhibition was augmented, indicating that strychnine binds to a position on the receptor physically distant from the flavonoid site. Potentiation of strychnine inhibition by flavonoids was also observed in vivo, where harmless doses of flavonoids enhanced strychnine toxicity in mice. Thus, in vitro and in vivo studies demonstrated a true synergism between flavonoids and strychnine for GlyR inhibition. The mechanism-based approach used here allows a rapid analysis of the effects of single drugs versus drug combinations.

  11. Unravelling mechanisms of dietary flavonoid-mediated health effects: effects on lipid metabolism and genotoxicity

    NARCIS (Netherlands)

    Hoek-van den Hil, E.F.

    2015-01-01

    Summary

    Consumption of foods containing flavonoids is associated with a reduced risk of cardiovascular diseases (CVD), possibly by lipid-lowering effects. On the other hand, for one of these flavonoids, quercetin, also genotoxicity was shown especially in in vitro

  12. The Association Between Dietary Flavonoid and Lignan Intakes and Incident Type 2 Diabetes in European Populations

    DEFF Research Database (Denmark)

    Zamora-Ros, Raul; Forouhi, Nita G.; Sharp, Stephen J.

    2013-01-01

    demonstrate inverse associations between flavonoids, particularly flavanols and flavonols, and incident type 2 diabetes. This suggests a potential protective role of eating a diet rich in flavonoids, a dietary pattern based on plant-based foods, in the prevention of type 2 diabetes....

  13. 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

    The bioavailability and urinary excretion of three dietary flavonoids, quercetin, hesperetin and naringenin, were investigated. Ten healthy men were asked to consume a 'juice mix' containing equal amounts of the three flavonoids, and their urine and plasma samples were collected. The resulting mean...

  14. Methylation of flavonoids: Chemical structures, bioactivities, progress and perspectives for biotechnological production.

    Science.gov (United States)

    Koirala, Niranjan; Thuan, Nguyen Huy; Ghimire, Gopal Prasad; Thang, Duong Van; Sohng, Jae Kyung

    2016-05-01

    Among the natural products, flavonoids have been particularly attractive, highly studied and become one of the most important promising agent to treat cancer, oxidant stress, pathogenic bacteria, inflammations, cardio-vascular dysfunctions, etc. Despite many promising roles of flavonoids, expectations have not been fulfilled when studies were extended to the in vivo condition, particularly in humans. Instability and very low oral bioavailability of dietary flavonoids are the reasons behind this. Researches have demonstrated that the methylation of these flavonoids could increase their promise as pharmaceutical agents leading to novel applications. Methylation of the flavonoids via theirs free hydroxyl groups or C atom dramatically increases their metabolic stability and enhances the membrane transport, leading to facilitated absorption and highly increased oral bioavailability. In this paper, we concentrated on analysis of flavonoid methoxides including O- and C-methoxide derivatives in aspect of structure, bioactivities and description of almost all up-to-date O- and C-methyltransferases' enzymatic characteristics. Furthermore, modern biological approaches for synthesis and production of flavonoid methoxides using metabolic engineering and synthetic biology have been focused and updated up to 2015. This review will give a handful information regarding the methylation of flavonoids, methyltransferases and biotechnological synthesis of the same. Copyright © 2016 Elsevier Inc. All rights reserved.

  15. Flavonoids Active Against Osteosarcoma: A Review of the Molecular Mechanisms Involved.

    Science.gov (United States)

    Liu, Hui; Gao, Yutong; Dong, Yonghui; Cheng, Peng; Chen, Anmin; Huang, Hui

    2017-01-01

    Osteosarcoma is the most frequent primitive malignant bone tumor affecting adolescents and young adults worldwide. The tumor exhibits aggressive growth in the primary site and readily metastasizes to other organs. There has been no significant improvement in the 5-year survival rate since the 1970s and the figure remains at 60-70%. In addition, the side effects of chemotherapeutic drugs and resistance to chemotherapy compromise the effects of treatment for osteosarcoma. In recent years, the development of flavonoids drugs inhibiting carcinogenesis is attracting great interest in the scientific community. Flavonoids are one kind of polyphenolic compounds widely found in vegetables and fruits. Moreover, flavonoids have become popular compounds, exhibiting comprehensive antitumor activities, while being safe and inexpensive. Here, the literature on the benefits afforded by flavonoids in terms of osteosarcoma treatment is reviewed and certain flavonoids and their effects on osteosarcoma are discussed. These compounds can perturb the cell cycle, induce apoptosis, inhibit tumor cell invasion and metastasis, potentiate the actions of chemotherapeutic agents, trigger autophagy, and stimulate antitumor activity in vivo. In summary, we highlight the currently well-accepted flavonoid compounds and detail the molecular mechanisms by which flavonoids may treat osteosarcoma, and thus the flavonoids exhibit great promise as anti-osteosarcoma agents. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  16. A study on the antitumour effect of total flavonoids from Pteris ...

    African Journals Online (AJOL)

    The objective of this paper was to investigate the inhibitory effect of total flavonoids from Pteris multifida Poir on growth of transplanted H22 tumour in mice. H22 tumour-bearing mice model was established; the experimental animals were divide/d into the model group, Pteris multifida Poir total flavonoids high-, low-dose ...

  17. Biosynthesis of flavonoids in bilberry and blueberry - possibilities of the gene level information for the future

    OpenAIRE

    Jaakola, Laura

    2007-01-01

    We have studied the biosynthesis of flavonoids in various tissues of naturally growing European blueberry (bilberry) and the blueberry cultivar 'Northblue'. Focus has also been on the biosynthesis of flavonoids in developing bilberry fruits as well as on the control genes regulating fruit development.

  18. [Separation and purification of flavonoids from chrysanthemum indicum with macroporous resin].

    Science.gov (United States)

    Yu, Jian-Sheng; Yu, Jian-Ping

    2007-10-01

    A method for separation and purification of flavonoids from C. indicum with macroporous resin was studied. By using C. indicum in Guizhou as the materials and with the content and recovery rate of flavonoids as indexes, the static and dynamic adsorption tests were employed to investigated effects and affective factors of separation and purification of flavonoids from C. indicum with macroporous resin. Results show that the static adsorption capacity of AB-8 type resin was 114.65 mg x g(-1), the static elution ratio were 94.9%, the dynamic adsorption capacity of AB-8 type resin was 94.5 mg x g(-1), the recovery rate was more than 92.6% and the purity of flavonoids was more than 90%. AB-8 type resin is the best for separating and purificating C. indicum in flavonoids. The optimum conditions is AB-8 type macroporous resin, 70% alcohol as the eluant and 2 to approximately 3 times volume of the resin as the eluant volume, the ratio of flavonoids to the volume of the resin as 1:10.6, concentration of flavonoids of sample as 19.8 mg x mL(-1) and current velocity as 2 to approximately 3 mL x min(-1), pH value of sample as 4 to approximately 5. [Key words]' macroporous resin; Chrysanthemum indicum; flavonoids; separation; purification

  19. 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...

  20. Deconjugation Kinetics of Glucuronidated Phase II Flavonoid Metabolites by B-glucuronidase from Neutrophils

    NARCIS (Netherlands)

    Bartholomé, R.; Haenen, G.; Hollman, P.C.H.; Bast, A.; Dagnelie, P.C.; Roos, D.; Keijer, J.; Kroon, P.A.; Needs, P.W.; Arts, I.C.W.

    2010-01-01

    Flavonoids are inactivated by phase II metabolism and occur in the body as glucuronides. Mammalian ß-glucuronidase released from neutrophils at inflammatory sites may be able to deconjugate and thus activate flavonoid glucuronides. We have studied deconjugation kinetics and pH optimum for four

  1. The Flavonoid Pathway in Tomato Seedlings: Transcript Abundance and the Modeling of Metabolite Dynamics

    NARCIS (Netherlands)

    Groenenboom, M.; Gomez-Roldan, V.; Stigter, J.D.; Astola, L.; Daelen, van R.; Beekwilder, M.J.; Bovy, A.G.; Hall, R.D.; Molenaar, J.

    2013-01-01

    Flavonoids are secondary metabolites present in all terrestrial plants. The flavonoid pathway has been extensively studied, and many of the involved genes and metabolites have been described in the literature. Despite this extensive knowledge, the functioning of the pathway in vivo is still poorly

  2. Deconjugation Kinetics of Glucuronidated Phase II Flavonoid Metabolites by beta-glucuronidase from Neutrophils

    NARCIS (Netherlands)

    Bartholomé, R.; Haenen, G.; Hollman, P.C.H.; Bast, A.; Dagnelie, P.C.; Roos, D.; Keijer, J.; Kroon, P.A.; Needs, P.W.; Arts, I.C.W.

    2010-01-01

    Flavonoids are inactivated by phase II metabolism and occur in the body as glucuronides. Mammalian beta-glucuronidase released from neutrophils at inflammatory sites may be able to deconjugate and thus activate flavonoid glucuronides. We have studied deconjugation kinetics and pH optimum for four

  3. Deconjugation kinetics of glucuronidated phase II flavonoid metabolites by beta-glucuronidase from neutrophils

    NARCIS (Netherlands)

    Bartholomé, Roger; Haenen, Guido; Hollman, C. H.; Bast, Aalt; Dagnelie, Pieter C.; Roos, Dirk; Keijer, Jaap; Kroon, Paul A.; Needs, Paul W.; Arts, Ilja C. W.

    2010-01-01

    Flavonoids are inactivated by phase II metabolism and occur in the body as glucuronides. Mammalian beta-glucuronidase released from neutrophils at inflammatory sites may be able to deconjugate and thus activate flavonoid glucuronides. We have studied deconjugation kinetics and pH optimum for four

  4. Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults.

    Science.gov (United States)

    Engler, Mary B; Engler, Marguerite M; Chen, Chung Y; Malloy, Mary J; Browne, Amanda; Chiu, Elisa Y; Kwak, Ho-Kyung; Milbury, Paul; Paul, Steven M; Blumberg, Jeffrey; Mietus-Snyder, Michele L

    2004-06-01

    Dark chocolate derived from the plant (Theobroma cacao) is a rich source of flavonoids. Cardioprotective effects including antioxidant properties, inhibition of platelet activity, and activation of endothelial nitric oxide synthase have been ascribed to the cocoa flavonoids. To investigate the effects of flavonoid-rich dark chocolate on endothelial function, measures of oxidative stress, blood lipids, and blood pressure in healthy adult subjects. The study was a randomized, double-blind, placebo-controlled design conducted over a 2 week period in 21 healthy adult subjects. Subjects were randomly assigned to daily intake of high-flavonoid (213 mg procyanidins, 46 mg epicatechin) or low-flavonoid dark chocolate bars (46 g, 1.6 oz). High-flavonoid chocolate consumption improved endothelium-dependent flow-mediated dilation (FMD) of the brachial artery (mean change = 1.3 +/- 0.7%) as compared to low-flavonoid chocolate consumption (mean change = -0.96 +/- 0.5%) (p = 0.024). No significant differences were noted in the resistance to LDL oxidation, total antioxidant capacity, 8-isoprostanes, blood pressure, lipid parameters, body weight or body mass index (BMI) between the two groups. Plasma epicatechin concentrations were markedly increased at 2 weeks in the high-flavonoid group (204.4 +/- 18.5 nmol/L, p chocolate improves endothelial function and is associated with an increase in plasma epicatechin concentrations in healthy adults. No changes in oxidative stress measures, lipid profiles, blood pressure, body weight or BMI were seen.

  5. Assessment of total flavonoid content and antioxidant activity of Mullein (Verbascum songaricum ecotypes

    Directory of Open Access Journals (Sweden)

    2017-11-01

    Full Text Available Background and objectives: The Mullein genus is the largest genus of Scrophulariaceae family which has extensive natural habitat in southwest of Iran. Mullein contains compounds such as phenolic compounds, mucilage, saponins and anthocyanin. The aim of this study was to evaluate the total flavonoid content and antioxidant activity of mullein ecotypes in Iran. Methods: Six ecotypes of the Verbascum songaricum were evaluated. Determination of total flavonoid content was performed bythealuminium chloride colourimetric method. The antioxidant activity of the flower extracts was measured using the DPPH method. Results: The results showed that total flavonoid content and antioxidant activity were different among ecotypes.  The highest and lowest amounts of total flavonoidwas obtained  from Shermard ecotype (13.42 mg rutin /g DW and Klar ecotypes(10.10 mg rutin /g DW, respectively. The highest amounts of antioxidant activity were obtained from the Shermard ecotype (IC50 246.35 μg/mL. The correlation analysis showed that a significant relation between flavonoid, antioxidant activity and habitat elevation. Conclusion: Total flavonoid content and antioxidant activity of the samples were affected by habitat climatic.  The present data indicated that the highest antioxidant activity may be due to higher flavonoid content and the habitat elevation was effective on the flavonoid content. Due to the high amounts of flavonoid and antioxidant activity of mullein extract, it seems to be a good herbal option as an antioxidant in complementary therapies.

  6. Ultraviolet light assisted extraction of flavonoids and allantoin from aqueous and alcoholic extracts of Symphytum officinale

    Directory of Open Access Journals (Sweden)

    Marwan S.M. Al-Nimer

    2017-09-01

    Conclusions: UV-radiation enhances the yields of active ingredient, of comfrey extracted with methanol whereas improves the flavonoids, reducing power and allantoin levels of comfrey extracted by the aqueous infusion method. UV-radiation reduces the levels of flavonoids, reducing power and allantoin when the comfrey extracted by alcohols [J Complement Med Res 2017; 6(3.000: 280-283

  7. [Purification of total flavonoids from the extracts of Thesium Chinese with macroporous adsorption resin].

    Science.gov (United States)

    Chu, Xiao-Qin; Hu, Ye-Qing; Yue, Lei

    2013-03-01

    To optimize the process parameters for purifying total flavonoids from Thesium chinese with D101 macroporous adsorption resin. Purification technology of total flavonoids from the extracts of Thesium chinese was investigated by dynamic adsorption method with the transfer rates and the purity of total flavonoids as indexes. The optimal purifying conditions were as follows: sample concentration was 2.259 mg/mL with a speed of 1 BV/h, eluent concentration was 70% alcohol with a speed of 1BV/h. After purification, the transfer rate of total flavonoids was 94.44% and the purity of total flavonoids achieved 12.45%, which was 4 times of that by coarse extraction (2.91%). The purification technology is simple, stable and can significantly improve the contents of total flavoids in extracts.

  8. [Preliminary study on purification technics of total flavonoids in Rhodiola dumulosa by macroporous resin].

    Science.gov (United States)

    Tan, Lin; Guo, Zeng-Jun; Xu, Ying

    2008-11-01

    To choose the best macroporous resin for purifying total flavonoids in Rhodiola dumulosa and study various factors affecting purification of resin in order to optimize the technics. Using methods combining static adsorption with desorption and dynamic adsorption with desorption, evaluating the technics by determination of total flavonoids in Rhodiola dumulosa using ultraviolet and visible spectrophotometry. The best macroporous resin was D101. The optimized technics were as follows: sample total flavonoids concentration was 3.625 mg/ml, adsorption velocity was 2 BV/h, desorption ethanol concentration was 95%, desorption velocity was 2 BV/h, eluant volume was 5 BV, the purity of total flavonoids could reach 48.5%. Purification performance of D101 macroporous resin is the best, and it is fit for the preliminary purification of total flavonoids in Rhodiola dumulosa.

  9. Mass spectrometric imaging of flavonoid glycosides and biflavonoids in Ginkgo biloba L.

    Science.gov (United States)

    Beck, Sebastian; Stengel, Julia

    2016-10-01

    Ginkgo biloba L. is known to be rich in flavonoids and flavonoid glycosides. However, the distribution within specific plant organs (e.g. within leaves) is not known. By using HPLC-MS and MS/MS we have identified a number of previously known G. biloba flavonoid glycosides and biflavonoids from leaves. Namely, kaempferol, quercetin, isorhamnetin, myricetin, laricitrin/mearnsetin and apigenin glycosides were identified. Furthermore, biflavonoids like ginkgetin/isoginkgetin were also detected. The application of MALDI mass spectrometric imaging, enabled the compilation of concentration profiles of flavonoid glycosides and biflavonoids in G. biloba L. leaves. Both, flavonoid glycosides and biflavonoids show a distinct distribution in leaf thin sections of G. biloba L. Copyright © 2016 Elsevier Ltd. All rights reserved.

  10. Chemosystematic significance of flavonoids isolated from Diplotaxis acris (Brassicaceae) and related taxa.

    Science.gov (United States)

    Hussein, Sameh R; Marzouk, Mona M; Kassem, Mona E S; Abdel Latif, Rasha R; Mohammed, Reda S

    2017-02-01

    The chemosystematic relationship of four Diplotaxis species; Diplotaxis acris, Diplotaxis erucoides, Diplotaxis harra and Diplotaxis muralis were surveyed from the flavonoids point of view. These species were found to produce 33 flavonoids (7 flavones and 26 flavonols), including 11 compounds were isolated in the present study from D. acris. Among them, seven flavonoids were identified for the first time; luteolin (4), kaempferol (8), kaempferol 3-O-β-glucopyranoside-7-O-α-rhamnopyranoside (13), quercetin 3-O-β-glucopyranoside (16), quercetin 7-O-β-glucopyranoside (20), isorhamnetin (22) and isorhamnetin 3-O-β-glucopyranoside-7-O-α-rhamnopyranoside (32). Their structures were recognized on the basis of chemical and spectroscopic techniques (1D & 2D NMR, UV, EI & ESI/MS). The isolated flavonoids may provide useful taxonomic characters at the infraspecific levels of classification where the flavonoid profile of D. acris and D. harra is similar and different from the other species.

  11. Effect of dry salting on flavonoid profile and antioxidant capacity of Algerian olive cultivars

    Energy Technology Data Exchange (ETDEWEB)

    Soufi, O.; Romero, C.; Motilva, M.J.; Borras Gaya, X.; Louaileche, H.

    2016-07-01

    This study investigated the changes in the flavonoid profile and antioxidant capacity of five olive cultivars after dry salting. The antioxidant activity was determined using ferric reducing ability power (FRAP), oxygen radical absorbance capacity (ORAC), and β-carotene bleaching assays. The results showed that the effects of dry salting on the analyzed parameters were significant (P<0.05). It caused a decrease in total flavonoids with a loss rate of 55%. The HPLC analysis of extracts revealed the presence of four flavonoids: rutin, luteolin-7-glucoside, cyanidin-3-glucoside and cyanidin-3-rutinoside. Among the studied cultivars, Azeradj was characterized by high levels of flavonoids. Concerning the antioxidant activity, diverging results were obtained using different antioxidant assays. Overall, the dry salting induced a reduction in the antioxidant activity with variable values depending on the cultivar. Among the used methods, high correlations were found between flavonoid contents and the FRAP assay. (Author)

  12. 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.

  13. DETERMINATION OF FLAVONOIDS AND ANTIOXIDANT ACTIVITY IN LAPHET LABORATORY PROCESS AND TEA (CAMELLIA SINENSIS) PRODUCTS BETWEEN CHINA AND MYANMAR

    OpenAIRE

    Pyie Phyo Maung; Qian He

    2013-01-01

    In this study, the effect of extraction method on the flavonoids and antioxidant activity was investigated. The flavonoid contents of Laphet(fermented pickled tea leaves) possessed more than twice as much than fresh tea leaves. Chinese green tea had higher flavonoid contents than Myanmar green tea. But Myanmar black tea’s flavonoid contents were higher. In laphet, both countries tea’s products possessed similar contents. Antioxidant activity of tea extracts were determined by using DPPH assay...

  14. Utilizing of Square Wave Voltammetry to Detect Flavonoids in the Presence of Human Urine

    Directory of Open Access Journals (Sweden)

    Rene Kizek

    2007-10-01

    Full Text Available About biological affecting of flavonoids on animal organisms is known less,thus we selected flavonoids, flavanones and flavones, and their glycosides, which wereexamined as potential inducers of cytochrome(s P450 when administrated by gavages intoexperimental male rats. The study was focused on induction of CYP1A1, the majorcytochrome P450 involved in carcinogen activation. The data obtained demonstrate thenecessity of taking into account not only ability of flavonoids to bind to Ah receptor(induction factor but also to concentrate on their distribution and metabolism (includingcolon microflora in the body. After that we examined certain flavonoids as potential inducers of cytochrome P450, we wanted to suggest and optimize suitable electrochemical technique for determination of selected flavonoids (quercetin, quercitrin, rutin, chrysin and diosmin in body liquids. For these purposes, we selected square wave voltannetry using carbon paste electrode. Primarily we aimed on investigation of their basic electrochemical behaviour. After that we have optimized frequency, step potential and supporting electrolyte. Based on the results obtained, we selected the most suitable conditions for determination of the flavonoids as follows: frequency 180 Hz, step potential 1.95 mV/s and phosphate buffer of pH 7 as supporting electrolyte. Detection limits (3 S/N of the flavonoids were from units to tens of nM except diosmin, where the limit were higher than μM. In addition, we attempted to suggest a sensor for analysis of flavonoids in urine. It clearly follows from the results obtained that flavonoids can be analysed in the presence of animal urine, because urine did not influence much the signals of flavonoids (recoveries of the signals were about 90 %.

  15. Flavonoid intake from food and beverages: What We Eat in America, NHANES 2007-2008, Tables 1-4

    Science.gov (United States)

    The Food Surveys Research Group of the Beltsville Human Nutrition Research Center has released 4 flavonoid intake data tables that make available, for the first time, nationally representative estimates of the intake of 29 individual flavonoids in six classes (as well as the sum of those flavonoids)...

  16. The antioxidants activity of flavonoids (procyanidol, quercetin, luteolin and kaempherol) in human lymphocytes exposed to ionizing radiation in vitro

    International Nuclear Information System (INIS)

    Stankovic, M.; Leskovac, A.; Petrovic, S.

    2007-01-01

    Phenolic components (flavonoids), may be important in prevention of DNA damage. We have tested the hypothesis that the flavonoids are protective against the DNA-damaging by γ-radiation in vitro. The study confirms strong antioxidant activity and radioprotective properties of flavonoids [sr

  17. [Flavonoid constituents from herbs of Sarcopyramis bodinieri var. delicata].

    Science.gov (United States)

    Wan, Chunpeng; Zheng, Xiao; Chen, Haifeng; Zou, Xiuhong; Song, Zirong; Zhou, Shouran; Qiu, Yan

    2009-01-01

    Phytochemical studies of the the herb Sarcopyramis bodinieri var. delicate (Melastomataceae) have been carried out. The compounds were separated by repeated D101 macroporous adsorption resin column combined with Sephadex LH-20, ODS, and silica gel chromatgrophy. The structures were identified on the basis of extensive spectroscopic data analysis, and by comparison of their spectral data with those reported. Eight flavonoid compounds isolated from the ethyl acetate extract was identified as isorhamnetin (1), quercetin (2), isorhamnetin-3-O-beta-D-glucopyranoside (3), quercetin-3-O-beta-D-glucopyranoside (4), isorhamnetin-3-O-(6"-acetyl)-beta-D-glucopyranoside (5), isorhamnetin-3-O-(2"-acetyl)-beta-D-glucopyranoside (6), quercetin-3-O-(6"-acetyl)-beta-D-glucopyranoside (7), and quercetin- 3-O-(6"-O-E-p-coumaroyl)-beta-D-glucopyranoside (8). All of the compounds were separated from the genus of Sarcopyramis for the first time.

  18. Flavonoid Compounds from the Bark of Aglaia eximia (Meliaceae

    Directory of Open Access Journals (Sweden)

    Julinton Sianturi

    2015-03-01

    Full Text Available Three flavonoid compounds, kaempferol (1, kaempferol-3-O-α-L-rhamnoside (2, and kaempferol-3-O-β-D-glucosyl-α-L-rhamnoside (3, were isolated from the bark of Aglaia eximia (Meliaceae. The chemical structures of compounds 1–3 were identified with spectroscopic data, including UV, IR, NMR (1H, 13C, DEPT 135°, HMQC, HMBC, 1H-1H-COSY NMR, and MS, as well as a compared with previously reported spectra data. All compounds were evaluated for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1–3 showed cytotoxicity against P-388 murine leukemia cells with IC50 values of 1.22, 42.92, and >100 mg/mL, respectively

  19. Antioxidant α-amylase inhibitors flavonoids from Iris germanica rhizomes

    Directory of Open Access Journals (Sweden)

    Sabrin Ibrahim

    Full Text Available ABSTRACT A new isoflavonoid glycoside, iridin A (9, along with eight known isoflavonoids: irilone 4'-methyl ether (1, irilone (2, irisolidone (3, irigenin S (4, irigenin (5, irilone 4'-O-β-D-glucopyranoside (6, iridin S (7, and iridin (8 were separated from Iris × germanica L., Iridaceae, rhizomes. The structural elucidation of these flavonoids was achieved with the aid of extensive spectroscopic techniques and comparing with the published data. They were estimated for their α-amylase and 1,1-diphenyl-2-picrylhydrazyl inhibitory capacities. Compounds 3, 5, and 9 showed α-amylase inhibitory activities with % inhibition 70.8, 67.5, and 70.5, respectively compared to acarbose (a reference α-amylase inhibitor. Moreover, 9 exhibited moderate antioxidant activity with IC50 8.91 µM.

  20. Signal Transduction and Molecular Targets of Selected Flavonoids

    Science.gov (United States)

    Bode, Ann M.

    2013-01-01

    Abstract Significance: Diet exerts a major influence on the risk for developing cancer and heart disease. Food factors such as flavonoids are alleged to protect cells from premature aging and disease by shielding DNA, proteins, and lipids from oxidative damage. Recent Advances: Our work has focused on clarifying the effects of dietary components on cancer cell proliferation and tumor growth, discovering mechanisms to explain the effects, and identifying the specific molecular targets of these compounds. Our strategy for identifying specific molecular targets of phytochemicals involves the use of supercomputer technology combined with protein crystallography, molecular biology, and experimental laboratory verification. Critical Issues: One of the greatest challenges for scientists is to reduce the accumulation of distortion and half truths reported in the popular media regarding the health benefits of certain foods or food supplements. The use of these is not new, but interest has increased dramatically because of perceived health benefits that are presumably acquired without unpleasant side effects. Flavonoids are touted to exert many beneficial effects in vitro. However, whether they can produce these effects in vivo is disputed. Future Directions: The World Health Organization indicates that one third of all cancer deaths are preventable and that diet is closely linked to prevention. Based on this idea and epidemiological findings, attention has centered on dietary phytochemicals as an effective intervention in cancer development. However, an unequivocal link between diet and cancer has not been established. Thus, identifying cancer preventive dietary agents with specific molecular targets is essential to move forward toward successful cancer prevention. Antioxid. Redox Signal. 19, 163–180. PMID:23458437