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Sample records for prenylated flavonoids present

  1. 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)

  2. 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)

  3. 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.

  4. Xanthohumol, a Prenylated Flavonoid from Hops (Humulus lupulus, Prevents Platelet Activation in Human Platelets

    Directory of Open Access Journals (Sweden)

    Ye-Ming Lee

    2012-01-01

    Full Text Available Xanthohumol is the principal prenylated flavonoid in the hop plant (Humulus lupulus L.. Xanthohumol was found to be a very potent cancer chemopreventive agent through regulation of diverse mechanisms. However, no data are available concerning the effects of xanthohumol on platelet activation. The aim of this paper was to examine the antiplatelet effect of xanthohumol in washed human platelets. In the present paper, xanthohumol exhibited more-potent activity in inhibiting platelet aggregation stimulated by collagen. Xanthohumol inhibited platelet activation accompanied by relative [Ca2+]i mobilization, thromboxane A2 formation, hydroxyl radical (OH● formation, and phospholipase C (PLCγ2, protein kinase C (PKC, mitogen-activated protein kinase (MAPK, and Akt phosphorylation. Neither SQ22536, an inhibitor of adenylate cyclase, nor ODQ, an inhibitor of guanylate cyclase, reversed the xanthohumol-mediated inhibitory effect on platelet aggregation. Furthermore, xanthohumol did not significantly increase nitrate formation in platelets. This study demonstrates for the first time that xanthohumol possesses potent antiplatelet activity which may initially inhibit the PI3-kinase/Akt, p38 MAPK, and PLCγ2-PKC cascades, followed by inhibition of the thromboxane A2 formation, thereby leading to inhibition of [Ca2+]i and finally inhibition of platelet aggregation. Therefore, this novel role of xanthohumol may represent a high therapeutic potential for treatment or prevention of cardiovascular diseases.

  5. Prenylated flavonoids as potent phosphodiesterase-4 inhibitors from Morus alba: Isolation, modification, and structure-activity relationship study.

    Science.gov (United States)

    Guo, Yan-Qiong; Tang, Gui-Hua; Lou, Lan-Lan; Li, Wei; Zhang, Bei; Liu, Bo; Yin, Sheng

    2018-01-20

    The bioassay-guided phytochemical study of a traditional Chinese medicine Morus alba led to the isolation of 18 prenylated flavonoids (1-18), of which (±)-cyclomorusin (1/2), a pair of enantiomers, and 14-methoxy-dihydromorusin (3) are the new ones. Subsequent structural modification of the selected components by methylation, esterification, hydrogenation, and oxidative cyclization led to 14 more derivatives (19-32). The small library was screened for its inhibition against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease (COPD). Among them, nine compounds (1-5, 8, 10, 16, and 17) exhibited remarkable activities with IC 50 values ranging from 0.0054 to 0.40 μM, being more active than the positive control rolipram (IC 50  = 0.62 μM). (+)-Cyclomorusin (1), the most active natural PDE4 inhibitor reported so far, also showed a high selectivity across other PDE members with the selective fold greater than 55. The SAR study revealed that the presence of prenyls at C-3 and/or C-8, 2H-pyran ring D, and the phenolic hydroxyl groups were important to the activity, which was further supported by the recognition mechanism study of the inhibitors with PDE4 by using molecular modeling. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  6. A comparative study on the metabolism of Epimedium koreanum Nakai-prenylated flavonoids in rats by an intestinal enzyme (lactase phlorizin hydrolase) and intestinal flora.

    Science.gov (United States)

    Zhou, Jing; Chen, Yan; Wang, Ying; Gao, Xia; Qu, Ding; Liu, Congyan

    2013-12-24

    The aim of this study was to compare the significance of the intestinal hydrolysis of prenylated flavonoids in Herba Epimedii by an intestinal enzyme and flora. Flavonoids were incubated at 37 °C with rat intestinal enzyme and intestinal flora. HPLC-UV was used to calculate the metabolic rates of the parent drug in the incubation and LC/MS/MS was used to determine the chemical structures of metabolites generated by different flavonoid glycosides. Rates of flavonoid metabolism by rat intestinal enzyme were quicker than those of intestinal flora. The sequence of intestinal flora metabolic rates was icariin>epimedin B>epimedin A>epimedin C>baohuoside I, whereas the order of intestinal enzyme metabolic rates was icariin>epimedin A>epimedin C>epimedin B>baohuoside I. Meanwhile, the LC/MS/MS graphs showed that icariin produced three products, epimedin A/B/C had four and baohuoside I yielded one product in incubations of both intestinal enzyme and flora, which were more than the results of HPLC-UV due to the fact LC/MS/MS has lower detectability and higher sensitivity. Moreover, the outcomes indicated that the rate of metabolization of flavonoids by intestinal enzyme were faster than those of intestinal flora, which was consistent with the HPLC-UV results. In conclusion, the metabolic pathways of the same components by intestinal flora and enzyme were the same. What's more, an intestinal enzyme such as lactase phlorizin hydrolase exhibited a more significant metabolic role in prenylated flavonoids of Herba Epimedi compared with intestinal flora.

  7. Impact of xanthohumol (a prenylated flavonoid from hops) on DNA stability and other health-related biochemical parameters

    DEFF Research Database (Denmark)

    Ferk, Franziska; Mišík, Miroslav; Nersesyan, Armen

    2016-01-01

    SCOPE: Xanthohumol (XN) is a hop flavonoid found in beers and refreshment drinks. Results of in vitro and animal studies indicate that it causes beneficial health effects due to DNA protective, anti-inflammatory, antioxidant, and phytoestrogenic properties. Aim of the present study was to find out...... if XN causes alterations of health-related parameters in humans. METHODS AND RESULTS: The effects of the flavonoid were investigated in a randomized crossover intervention trial (n = 22) in which the participants consumed a XN drink (12 mg XN/P/day). We monitored alterations of the DNA stability......'-deoxyguanosine and 8-oxo-guanosine in urine was reduced. The assumption that the flavonoid causes DNA protection was confirmed in a randomized follow-up study with pure XN (n = 10) with a parallel design. Other biochemical parameters reflecting the redox- and hormonal status and lipid- and glucose metabolism...

  8. Isolation of two new prenylated flavonoids from Sinopodophyllum emodi fruit by silica gel column and high-speed counter-current chromatography.

    Science.gov (United States)

    Sun, Yanjun; Sun, Yinshi; Chen, Hui; Hao, Zhiyou; Wang, Junmin; Guan, Yanbin; Zhang, Yanli; Feng, Weisheng; Zheng, Xiaoke

    2014-10-15

    Two new prenylated flavonoids, sinoflavonoids A-B, were isolated from the dried fruits of Sinopodophyllum emodi by silica gel column chromatography (SGCC) and high-speed counter-current chromatography (HSCCC). The 95% ethanol extract was partitioned with petroleum ether, dichloromethane, ethyl acetate, and n-butanol in water, respectively. The ethyl acetate fraction was pre-separated by SGCC with a petroleum ether-acetone gradient. The eluates containing target compounds were further separated by HSCCC with n-hexane-ethyl acetate-methanol-water (4:6:4:4, v/v). Finally, 17.3mg of sinoflavonoid A and 25.9mg of sinoflavonoid B were obtained from 100mg of the pretreated concentrate. The purities of sinoflavonoid A and sinoflavonoid B were 98.47% and 99.38%, respectively, as determined by HPLC. Their structures were elucidated on the basis of spectroscopic evidences (HR-ESI-MS, (1)H-NMR, (13)C-NMR, HSQC, HMBC). The separation procedures proved to be efficient, especially for trace prenylated flavonoids. Copyright © 2014 Elsevier B.V. All rights reserved.

  9. Pharmacological Profile of Xanthohumol, a Prenylated Flavonoid from Hops (Humulus lupulus

    Directory of Open Access Journals (Sweden)

    Ming Liu

    2015-01-01

    Full Text Available The female inflorescences of hops (Humulus lupulus L., a well-known bittering agent used in the brewing industry, have long been used in traditional medicines. Xanthohumol (XN is one of the bioactive substances contributing to its medical applications. Among foodstuffs XN is found primarily in beer and its natural occurrence is surveyed. In recent years, XN has received much attention for its biological effects. The present review describes the pharmacological aspects of XN and summarizes the most interesting findings obtained in the preclinical research related to this compound, including the pharmacological activity, the pharmacokinetics, and the safety of XN. Furthermore, the potential use of XN as a food additive considering its many positive biological effects is discussed.

  10. Neuroprotective effect of prenylated arylbenzofuran and flavonoids from morus alba fruits on glutamate-induced oxidative injury in HT22 hippocampal cells.

    Science.gov (United States)

    Seo, Kyeong-Hwa; Lee, Dae-Young; Jeong, Rak-Hun; Lee, Dong-Sung; Kim, Young-Eon; Hong, Eock-Kee; Kim, Youn-Chul; Baek, Nam-In

    2015-04-01

    A prenylated arylbenzofuran and six flavonoids were isolated from the fruits of Morus alba L. through silica gel, octadecyl silica gel, and Diaion HP-20 column chromatography. Based on the nuclear magnetic resonance, mass spectrometry, and infrared spectroscopic data, the chemical structures of the compounds were determined to be artoindonesianin O (1), isobavachalcone (2), morachalcone A (3), quercetin (4), astragalin (5), isoquercetin (6), and rutin (7). The isolated compounds were evaluated for protection of HT22-immortalized hippocampal cells against glutamate-induced oxidative stress. Compounds 1 and 3 exhibited protective effects with EC(50) values of 19.7±1.2 and 35.5±2.1 μM, respectively. The major compounds 1-3 and 7 were quantified using liquid chromatography/mass spectrometry analysis and were determined to be 1.88±2.1, 1.90±1.8, 0.78±1.5, and 37.29±2.2 mg/kg, respectively, in the ethanol extract of M. alba L. fruits.

  11. Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium.

    Science.gov (United States)

    Popoola, Olugbenga K; Marnewick, Jeanine L; Rautenbach, Fanie; Ameer, Farouk; Iwuoha, Emmanuel I; Hussein, Ahmed A

    2015-04-20

    Ten flavonoid-related structures viz. heliteretifolin (1), isoxanthohumol (2), 2',4',6'-trihydroxy-3'-prenylchalcone (3), isoglabranin (4), glabranin (5), 7-methoxy-isoglabranin (6), quercetin (7), 4'-methoxyquercetin (8), 4'-methoxykaempferol (9) and mosloflavone (10) were isolated from a H. teretifolium methanolic extract and identified. One of them (compound 1) is reported for the first time from a natural source, while compounds 6, 8-10 were isolated for the first time from the genus Helichrysum. The total extract of H. teretifolium showed potent antioxidant activity. When tested for total antioxidant capacity compound 3 possesses moderate biological activity compared to 2, which displayed some of the highest TEAC values (4529.01 ± 2.44; 4170.66 ± 6.72) µM TE/g, respectively. Compounds 7 and 8 demonstrated the highest inhibitory activities on Fe2+-induced lipid peroxidation (IC50 = 2.931; 6.449 µg/mL); tyrosinase (8.092; 27.573) and elastase (43.342; 86.548). Additionally, the total antioxidant capacities measured as FRAP (4816.31 ± 7.42; 3584.17 ± 0.54) µM AAE/g, and ORAC for hydroxyl radical (7.265 ± 0.71; 6.779 ± 3.40) × 106 and peroxyl radical (17.836 ± 2.90; 12.545 ± 5.07) × 103 µM TE/g were also observed for compounds 7 and 8, respectively. In conclusion, H. teretifolium total extract represents a rich source of bioactive constituents with potent antioxidant and moderate anti-tyrosinase and anti-elastase activities that can help to avert accumulation of free radicals in the body, and could therefore be good candidates for the prevention and/or treatment of skin-related conditions, such as aging. This is the first scientific report on the chemical and biological profile of H. teretifolium.

  12. Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

    Directory of Open Access Journals (Sweden)

    Olugbenga K. Popoola

    2015-04-01

    Full Text Available Ten flavonoid-related structures viz. heliteretifolin (1, isoxanthohumol (2, 2',4',6'-trihydroxy-3'-prenylchalcone (3, isoglabranin (4, glabranin (5, 7-methoxy-isoglabranin (6, quercetin (7, 4'-methoxyquercetin (8, 4'-methoxykaempferol (9 and mosloflavone (10 were isolated from a H. teretifolium methanolic extract and identified. One of them (compound 1 is reported for the first time from a natural source, while compounds 6, 8–10 were isolated for the first time from the genus Helichrysum. The total extract of H. teretifolium showed potent antioxidant activity. When tested for total antioxidant capacity compound 3 possesses moderate biological activity compared to 2, which displayed some of the highest TEAC values (4529.01 ± 2.44; 4170.66 ± 6.72 µM TE/g, respectively. Compounds 7 and 8 demonstrated the highest inhibitory activities on Fe2+-induced lipid peroxidation (IC50 = 2.931; 6.449 µg/mL; tyrosinase (8.092; 27.573 and elastase (43.342; 86.548. Additionally, the total antioxidant capacities measured as FRAP (4816.31 ± 7.42; 3584.17 ± 0.54 µM AAE/g, and ORAC for hydroxyl radical (7.265 ± 0.71; 6.779 ± 3.40 × 106 and peroxyl radical (17.836 ± 2.90; 12.545 ± 5.07 × 103 µM TE/g were also observed for compounds 7 and 8, respectively. In conclusion, H. teretifolium total extract represents a rich source of bioactive constituents with potent antioxidant and moderate anti-tyrosinase and anti-elastase activities that can help to avert accumulation of free radicals in the body, and could therefore be good candidates for the prevention and/or treatment of skin-related conditions, such as aging. This is the first scientific report on the chemical and biological profile of H. teretifolium.

  13. Prenylated Flavonoids from Morus alba L. Cause Inhibition of G1/S Transition in THP-1 Human Leukemia Cells and Prevent the Lipopolysaccharide-Induced Inflammatory Response

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    Peter Kollar

    2013-01-01

    Full Text Available Morus alba L. (MA is a natural source of many compounds with different biological effects. It has been described to possess anti-inflammatory, antioxidant, and hepatoprotective activities. The aim of this study was to evaluate cytotoxicity of three flavonoids isolated from MA (kuwanon E, cudraflavone B, and 4′-O-methylkuwanon E and to determine their effects on proliferation of THP-1 cells, and on cell cycle progression of cancer cells. Anti-inflammatory effects were also determined for all three given flavonoids. Methods used in the study included quantification of cells by hemocytometer and WST-1 assays, flow cytometry, western blotting, ELISA, and zymography. From the three compounds tested, cudraflavone B showed the strongest effects on cell cycle progression and viability of tumor and/or immortalized cells and also on inflammatory response of macrophage-like cells. Kuwanon E and 4′-O-methylkuwanon E exerted more sophisticated rather than direct toxic effect on used cell types. Our data indicate that mechanisms different from stress-related or apoptotic signaling pathways are involved in the action of these compounds. Although further studies are required to precisely define the mechanisms of MA flavonoid action in human cancer and macrophage-like cells, here we demonstrate their effects combining antiproliferative and anti-inflammatory activities, respectively.

  14. Xanthohumol, a prenylated flavonoid contained in beer, prevents the induction of preneoplastic lesions and DNA damage in liver and colon induced by the heterocyclic aromatic amine amino-3-methyl-imidazo[4,5-f]quinoline (IQ)

    International Nuclear Information System (INIS)

    Ferk, Franziska; Huber, Wolfgang W.; Filipic, Metka; Bichler, Julia; Haslinger, Elisabeth; Misik, Miroslav; Nersesyan, Armen; Grasl-Kraupp, Bettina; Zegura, Bojana; Knasmueller, Siegfried

    2010-01-01

    Xanthohumol (XN) is a hop derived prenylated flavonoid contained in beer. Earlier findings indicated that it has promising chemopreventive properties and protects cells against DNA damage by carcinogens via inhibition of their activation. Furthermore, it was found that XN inhibits DNA synthesis and proliferation of cancer cells in vitro, inactivates oxygen radicals and induces apoptosis. Since evidence for its chemoprotective properties is restricted to results from in vitro experiments, we monitored the impact of XN on the formation of amino-3-methyl-imidazo[4,5-f]quinoline (IQ)-induced preneoplastic foci in livers and colons of rats (9/group). Additionally, we studied its effects on IQ-induced DNA damage in colonocytes and hepatocytes in single cell gel electrophoresis assays and on the activities of a panel of drug metabolising enzymes. Consumption of the drinking water supplemented with XN (71 μg/kg b.w.) before and during carcinogen treatment led to a significant reduction of the number of GST-p + foci in the liver by 50% and also to a decrease of the foci area by 44%. DNA migration was decreased significantly in both, colon mucosa and liver cells, but no alterations of the activities of different phases I and II enzymes were found in hepatic tissue. Our findings indicate that XN protects against DNA damage and cancer induced by the cooked food mutagen. Since the effects were observed with low doses of XN which are reached after consumption of brews with high XN levels, our findings may be relevant for humans.

  15. Identification of prenylated pterocarpans and other isoflavonoids in Rhizopus spp. elicited soya bean seedlings by electrospray ionisation mass spectrometry.

    Science.gov (United States)

    Simons, Rudy; Vincken, Jean-Paul; Bohin, Maxime C; Kuijpers, Tomas F M; Verbruggen, Marian A; Gruppen, Harry

    2011-01-15

    Phytoalexins from soya are mainly characterised as prenylated pterocarpans, the glyceollins. Extracts of non-soaked and soaked soya beans, as well as that of soya seedlings, grown in the presence of Rhizopus microsporus var. oryzae, were screened for the presence of prenylated flavonoids with a liquid chromatography/mass spectrometry (LC/MS)-based screening method. The glyceollins I-III and glyceollidins I-II, belonging to the isoflavonoid subclass of the pterocarpans, were tentatively assigned. The formation of these prenylated pterocarpans was accompanied by that of other prenylated isoflavonoids of the subclasses of the isoflavones and the coumestans. It was estimated that approx. 40% of the total isoflavonoid content in Rhizopus-challenged soya bean seedlings were prenylated pterocarpans, whereas 7% comprised prenylated isoflavones and prenylated coumestans. The site of prenylation (A-ring or B-ring) of the prenylated isoflavones was tentatively annotated using positive-ion mode MS by comparing the (1,3) A(+) retro-Diels-Alder (RDA) fragments of prenylated and non-prenylated isoflavones. Furthermore, the fragmentation pathways of the five pterocarpans in negative-ion (NI) mode were proposed, which involved the cleavage of the C-ring and/or D-ring. The absence of the ring-closed prenyl (pyran or furan) gave exclusively -H(2) O(x,y) RDA fragments, whereas its presence gave predominantly the common RDA fragments. Copyright © 2010 John Wiley & Sons, Ltd.

  16. Identification of prenylated pterocarpans and other isoflavonoids in Rhizopus spp. elicited soya bean seedlings by electrospray ionisation mass spectrometry

    NARCIS (Netherlands)

    Simons, R.; Vincken, J.P.; Bohin, M.C.; Kuijpers, T.F.M.; Verbruggen, M.A.; Gruppen, H.

    2011-01-01

    Phytoalexins from soya are mainly characterised as prenylated pterocarpans, the glyceollins. Extracts of non-soaked and soaked soya beans, as well as that of soya seedlings, grown in the presence of Rhizopus microsporus var. oryzae, were screened for the presence of prenylated flavonoids with a

  17. Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata*

    Science.gov (United States)

    Wang, Ruishan; Chen, Ridao; Li, Jianhua; Liu, Xiao; Xie, Kebo; Chen, Dawei; Yin, Yunze; Tao, Xiaoyu; Xie, Dan; Zou, Jianhua; Yang, Lin; Dai, Jungui

    2014-01-01

    Prenylated flavonoids are attractive specialized metabolites with a wide range of biological activities and are distributed in several plant families. The prenylation catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylated flavonoids and contributes to the structural diversity and biological activities of these compounds. To date, all identified plant flavonoid prenyltransferases (FPTs) have been identified in Leguminosae. In the present study two new FPTs, Morus alba isoliquiritigenin 3′-dimethylallyltransferase (MaIDT) and Cudrania tricuspidata isoliquiritigenin 3′-dimethylallyltransferase (CtIDT), were identified from moraceous plants M. alba and C. tricuspidata, respectively. MaIDT and CtIDT shared low levels of homology with the leguminous FPTs. MaIDT and CtIDT are predicted to be membrane-bound proteins with predicted transit peptides, seven transmembrane regions, and conserved functional domains that are similar to other homogentisate prenyltransferases. Recombinant MaIDT and CtIDT were able to regioselectively introduce dimethylallyl diphosphate into the A ring of three flavonoids with different skeleton types (chalcones, isoflavones, and flavones). Phylogenetic analysis revealed that MaIDT and CtIDT are distantly related to their homologs in Leguminosae, which suggests that FPTs in Moraceae and Leguminosae might have evolved independently. MaIDT and CtIDT represent the first two non-Leguminosae FPTs to be identified in plants and could thus lead to the identification of additional evolutionarily varied FPTs in other non-Leguminosae plants and could elucidate the biosyntheses of prenylated flavonoids in various plants. Furthermore, MaIDT and CtIDT might be used for regiospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications due to their high efficiency and catalytic promiscuity. PMID:25361766

  18. Molecular characterization and phylogenetic analysis of two novel regio-specific flavonoid prenyltransferases from Morus alba and Cudrania tricuspidata.

    Science.gov (United States)

    Wang, Ruishan; Chen, Ridao; Li, Jianhua; Liu, Xiao; Xie, Kebo; Chen, Dawei; Yin, Yunze; Tao, Xiaoyu; Xie, Dan; Zou, Jianhua; Yang, Lin; Dai, Jungui

    2014-12-26

    Prenylated flavonoids are attractive specialized metabolites with a wide range of biological activities and are distributed in several plant families. The prenylation catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylated flavonoids and contributes to the structural diversity and biological activities of these compounds. To date, all identified plant flavonoid prenyltransferases (FPTs) have been identified in Leguminosae. In the present study two new FPTs, Morus alba isoliquiritigenin 3'-dimethylallyltransferase (MaIDT) and Cudrania tricuspidata isoliquiritigenin 3'-dimethylallyltransferase (CtIDT), were identified from moraceous plants M. alba and C. tricuspidata, respectively. MaIDT and CtIDT shared low levels of homology with the leguminous FPTs. MaIDT and CtIDT are predicted to be membrane-bound proteins with predicted transit peptides, seven transmembrane regions, and conserved functional domains that are similar to other homogentisate prenyltransferases. Recombinant MaIDT and CtIDT were able to regioselectively introduce dimethylallyl diphosphate into the A ring of three flavonoids with different skeleton types (chalcones, isoflavones, and flavones). Phylogenetic analysis revealed that MaIDT and CtIDT are distantly related to their homologs in Leguminosae, which suggests that FPTs in Moraceae and Leguminosae might have evolved independently. MaIDT and CtIDT represent the first two non-Leguminosae FPTs to be identified in plants and could thus lead to the identification of additional evolutionarily varied FPTs in other non-Leguminosae plants and could elucidate the biosyntheses of prenylated flavonoids in various plants. Furthermore, MaIDT and CtIDT might be used for regiospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications due to their high efficiency and catalytic promiscuity. © 2014 by The American Society for Biochemistry

  19. 3-Prenyl luteolin, a new prenylated flavone with melanin biosynthesis inhibitory activity from wood of Artocarpus heterophyllus.

    Science.gov (United States)

    Arung, Enos Tangke; Shimizu, Kuniyoshi; Tanaka, Hiroyuki; Kondo, Ryuichiro

    2010-09-01

    In our efforts to find new whitening agent from natural resources, we focused on wood of Artocarpus heterophyllus which shows anti-melanogenesis activity. By activity-guided fractionation of A. heterophyllus wood extract, a new prenylated flavonoid, 3-prenyl luteolin (1) was isolated. The IC(50) of mushroom tyrosinase inhibitory activity of 1 was 76.3 microM. The results of the comparison with that of luteolin showed the prenyl substituent at C-3 position of 1 play an important role for revealing tyrosinase inhibition. In melanin formation inhibition on B16 melanoma cells, IC(50) of 1 was 56.7 microM with less cytotoxicity. Copyright (c) 2010 Elsevier B.V. All rights reserved.

  20. Modification of abomasum contractility by flavonoids present in ruminants diet: in vitro study.

    Science.gov (United States)

    Mendel, M; Chłopecka, M; Dziekan, N; Karlik, W

    2016-09-01

    Flavonoid supplementation is likely to be beneficial in improving rumen fermentation and in reducing the incidence of rumen acidosis and bloat. Flavonoids are also said to increase the metabolic performance during the peripartum period. Ruminants are constantly exposed to flavonoids present in feed. However, it is not clear if these phytochemicals can affect the activity of the gut smooth muscle. Therefore, the aim of the study was to verify the effect of three flavonoids on bovine isolated abomasum smooth muscle. The study was carried out on bovine isolated circular and longitudinal abomasal smooth muscle specimens. All experiments were conducted under isometric conditions. The effect of apigenin, luteolin and quercetin (0.001 to 100 µM) was evaluated on acetylcholine-precontracted preparations. The effect of multiple, but not cumulative, treatment and single treatment with each flavonoid on abomasum strips was compared. Apigenin (0.1 to 100 µM) dose-dependently showed myorelaxation effects. Luteolin and quercetin applied in low doses increased the force of the ACh-evoked reaction. However, if used in high doses in experiments testing a wide range of concentrations, their contractile effect either declined (luteolin) or was replaced by an antispasmodic effect (quercetin). Surprisingly, the reaction induced by flavonoids after repeated exposure to the same phytochemical was not reproducible in experiments testing only single exposure of abomasum strips to the same flavonoid used in a high concentration. Taking into account the physicochemical properties of flavonoids, this data suggests the ability of flavonoids to interfere with cell membranes and, subsequently, to modify their responsiveness. Assuming ruminant supplementation with luteolin or quercetin or their presence in daily pasture, a reduction of the likelihood of abomasum dysmotility should be expected.

  1. Flavonoid electrochemistry: a review on the electroanalytical applications

    Directory of Open Access Journals (Sweden)

    Eric S. Gil

    2013-05-01

    Full Text Available Flavonoids are polyphenolic compounds widespread in vegetal kingdom. They present a C-15 skeleton, which is divided into three units A, B and C. Unit C is an oxygen containing heterocyclic, whose oxidation state and saturation level define major subclasses. Units A and B are aromatic rings, in which four major types of substituents, i. e. hydroxyl, methoxyl, prenyl and glycosides, lead to over 8000 different flavonoids. The great healthy-protecting value of these phytochemical biomarkers has attracted the attention of scientific community. Their main biological actions include anticancer and anti-inflammatory properties, which are strictly linked to antioxidant activities. So that, electroanalysis have been extensively applied on mechanistic studies and also for analytical determinations. This review presents the state of the art regarding the main applications of electroanalysis on the flavonoid research. The approaches on redox behavior characterization leading to a better understanding of structure antioxidant activity relationships are highlighted.

  2. Flavonoid electrochemistry: a review on the electroanalytical applications

    Directory of Open Access Journals (Sweden)

    Eric S. Gil

    2013-06-01

    Full Text Available Flavonoids are polyphenolic compounds widespread in vegetal kingdom. They present a C-15 skeleton, which is divided into three units A, B and C. Unit C is an oxygen containing heterocyclic, whose oxidation state and saturation level define major subclasses. Units A and B are aromatic rings, in which four major types of substituents, i. e. hydroxyl, methoxyl, prenyl and glycosides, lead to over 8000 different flavonoids. The great healthy-protecting value of these phytochemical biomarkers has attracted the attention of scientific community. Their main biological actions include anticancer and anti-inflammatory properties, which are strictly linked to antioxidant activities. So that, electroanalysis have been extensively applied on mechanistic studies and also for analytical determinations. This review presents the state of the art regarding the main applications of electroanalysis on the flavonoid research. The approaches on redox behavior characterization leading to a better understanding of structure antioxidant activity relationships are highlighted.

  3. Pinostrobin Derivatives from PrenylationReaction and their Antibacterial Activity against Clinical Bacteria

    Science.gov (United States)

    Marliyana, S. D.; Mujahidin, D.; Syah, Y. M.

    2018-04-01

    Kaempferia pandurata (syn. Boesenbergia rotunda, B. pandurata (Roxb.)Schltr), locally known as "TemuKunci"in Indonesia, is one of the medicinal plants of the family Zingiberaceae. Phytochemical studies on the rhizome of K. pandurata showed the presence of flavonoid derivative, namely flavanones, which constitute as the main components of this plant. Bioactivity studies on this species exhibited various biological activities, such as antibacteria, anti-inflammatory, antitumor, antidiarrhea, antidisentri, anti-HIV, antioxidant, antipyretic, analgesic and insecticides. Among the biological activities, the antibacterial activity results are important as an attempt to answer the emergence of resistance of some bacteria against existing drugs, as well as the emergence of a number of outbreaks of disease caused by bacteria. Therefore, a search to find new compounds that are potential as an antibacterial is an urgent matter. The present study was aimed at the chemical transformation of pinostrobin (1) from K. pandurata rhizome and an antibacterial activity.The chemical transformation was performed through a prenylation reaction of pinostrobin (1) which is the main component of K. pandurata rhizome. The prenylation reaction was carried out by reacting pinostrobin (1) with prenyl bromide and potassium carbonat (K2CO3). The purification of product was done using the radial chromatography with mix solvent n-hexane and ethyl acetate (97.5:2.5; 9.5:0.5; 9.0:1.0.; 8.0:2.0). The purity test of isolated compound was analysedby TLC using different types of eluent. The identification of compounds was determined based on NMR data and mass spectra analysis. Five compounds were obtained from the prenylation reaction, i.e. monooxyprenylated pinostrobin (2), monooxyprenylated chalcone (3), diprenylated chalcone (4), triprenylated chalcone (5), and triprenylated cyclohexene chalcone (6). These compounds were tested for antibacterial activities against four clinical bacteria, namely

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

    Science.gov (United States)

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

    2008-02-01

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

  5. Synthesis and Antiproliferative Activity of Minor Hops Prenylflavonoids and New Insights on Prenyl Group Cyclization

    Directory of Open Access Journals (Sweden)

    Jarosław Popłoński

    2018-03-01

    Full Text Available Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops as a lead compound, a series of minor hop prenylflavonoids and synthetic derivatives were obtained by isomerization, cyclisation, oxidative-cyclisation, oxidation, reduction and demethylation reactions. Three human cancer cell lines—breast (MCF-7, prostate (PC-3 and colon (HT-29—were used in antiproliferative assays, with cisplatin as a control compound. Five minor hop prenyl flavonoids and nine non-natural derivatives of xanthohumol have been synthetized. Syntheses of xanthohumol K, its dihydro- and tetrahydro-derivatives and 1″,2″,α,β-tetrahydroxanthohumol C were described for the first time. All of the minor hops prenyl flavonoids exhibited strong to moderate antiproliferative activity in vitro. The minor hops flavonoids xanthohumol C and 1″,2″-dihydroxanthohumol K and non-natural 2,3-dehydroisoxanthohumol exhibited the activity comparable to cisplatin. Results described in the article suggest that flavonoids containing chromane- and chromene-like moieties, especially chalcones, are potent antiproliferative agents. The developed new efficient, regioselective cyclisation reaction of the xanthohumol prenyl group to 1″,2″-dihydroxantohumol K may be used in the synthesis of other compounds with the chromane moiety.

  6. 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

  7. Evaluation of anti-inflammatory activity of prenylated substances isolated from Morus alba and Morus nigra.

    Science.gov (United States)

    Zelová, Hana; Hanáková, Zuzana; Čermáková, Zuzana; Šmejkal, Karel; Dalĺ Acqua, Stefano; Babula, Petr; Cvačka, Josef; Hošek, Jan

    2014-06-27

    Chromatographic separation of root extracts of Morus alba and M. nigra led to the identification of the 2-arylbenzofurans moracin C (1), mulberrofuran Y (2), and mulberrofuran H (3), and the prenylated flavonoids kuwanon E (4), kuwanon C (5), sanggenon H (6), cudraflavone B (7), and morusinol (8), and the Diels-Alder adducts soroceal (9), and sanggenon E (10). The cytotoxicity and their antiphlogistic activity, determined as the attenuation of the secretion of TNF-α and IL-1β and the inhibition of NF-κB nuclear translocation in LPS-stimulated macrophages, were evaluated for compounds 1-10.

  8. Prenylated and geranylated chalcones and flavones from the aerial parts of Dorstenia ciliata

    Directory of Open Access Journals (Sweden)

    Simeon F. Kouam

    2002-12-01

    Full Text Available Investigation of the aerial parts of Dorstenia ciliata yielded two new prenylated flavones named ciliatins A and B and characterized as 6,7-(2’’-isopropenyldihydrofurano-5,4’-dihydroxyflavone and 6,5-(2,2-dimethyldihydropyrano-7,4’-dihydroxy-3’-methoxyflavone, respectively. Known flavonoids: stipulin, isobavachalcone, licoflavone C, 6-prenylapigenin, dinklagin C, gancaonin P, canniflavone and poinsettifolin A were also identified. Structures of these secondary metabolites were established on the basis of spectroscopic analysis, comparison with published information and with authentic specimen for some cases and chemical evidence for the dihydropyranoflavone derivative.

  9. Protein prenylation: a new mode of host-pathogen interaction.

    Science.gov (United States)

    Amaya, Moushimi; Baranova, Ancha; van Hoek, Monique L

    2011-12-09

    Post translational modifications are required for proteins to be fully functional. The three step process, prenylation, leads to farnesylation or geranylgeranylation, which increase the hydrophobicity of the prenylated protein for efficient anchoring into plasma membranes and/or organellar membranes. Prenylated proteins function in a number of signaling and regulatory pathways that are responsible for basic cell operations. Well characterized prenylated proteins include Ras, Rac and Rho. Recently, pathogenic prokaryotic proteins, such as SifA and AnkB, have been shown to be prenylated by eukaryotic host cell machinery, but their functions remain elusive. The identification of other bacterial proteins undergoing this type of host-directed post-translational modification shows promise in elucidating host-pathogen interactions to develop new therapeutics. This review incorporates new advances in the study of protein prenylation into a broader aspect of biology with a focus on host-pathogen interaction. Copyright © 2011 Elsevier Inc. All rights reserved.

  10. 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.

  11. 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.

  12. Xanthohumol, a Prenylated Chalcone from Hops, Inhibits the Viability and Stemness of Doxorubicin-Resistant MCF-7/ADR Cells

    Directory of Open Access Journals (Sweden)

    Ming Liu

    2016-12-01

    Full Text Available Xanthohumol is a unique prenylated flavonoid in hops (Humulus lupulus L. and beer. Xanthohumol has been shown to possess a variety of pharmacological activities. There is little research on its effect on doxorubicin-resistant breast cancer cells (MCF-7/ADR and the cancer stem-like cells exiting in this cell line. In the present study, we investigate the effect of xanthohumol on the viability and stemness of MCF-7/ADR cells. Xanthohumol inhibits viability, induces apoptosis, and arrests the cell cycle of MCF-7/ADR cells in a dose-dependent manner; in addition, xanthohumol sensitizes the inhibition effect of doxorubicin on MCF-7/ADR cells. Interestingly, we also find that xanthohumol can reduce the stemness of MCF-7/ADR cells evidenced by the xanthohumol-induced decrease in the colony formation, the migration, the percentage of side population cells, the sphere formation, and the down-regulation of stemness-related biomarkers. These results demonstrate that xanthohumol is a promising compound targeting the doxorubicin resistant breast cancer cells and regulating their stemness, which, therefore, will be applied as a potential candidate for the development of a doxorubicin-resistant breast cancer agent and combination therapy of breast cancer.

  13. 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...

  14. Anti-inflammatory Activity of Natural Geranylated Flavonoids: Cyclooxygenase and Lipoxygenase Inhibitory Properties and Proteomic Analysis

    Czech Academy of Sciences Publication Activity Database

    Hanáková, Z.; Hošek, J.; Kutil, Zsófia; Temml, V.; Landa, Přemysl; Vaněk, Tomáš; Schuster, D.; Dall’Acqua, S.; Cvačka, Josef; Polanský, O.; Šmejkal, K.

    2017-01-01

    Roč. 80, č. 4 (2017), s. 999-1006 ISSN 0163-3864 Grant - others:GA MŠk(CZ) ED0006/01/01 Institutional support: RVO:61389030 ; RVO:61388963 Keywords : PAULOWNIA-TOMENTOSA FRUITS * PRENYLATED FLAVONOIDS * FLAVANONES Subject RIV: CE - Biochemistry OBOR OECD: Biochemistry and molecular biology Impact factor: 3.281, year: 2016

  15. Sensor Function for Butyrophilin 3A1 in Prenyl Pyrophosphate Stimulation of Human Vγ2Vδ2 T Cells

    Science.gov (United States)

    Wang, Hong; Morita, Craig T.

    2016-01-01

    Vγ2Vδ2 T cells play important roles in human immunity to pathogens and in cancer immunotherapy by responding to isoprenoid metabolites, such as (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate and isopentenyl pyrophosphate. The Ig superfamily protein butyrophilin (BTN)3A1 was shown to be required for prenyl pyrophosphate stimulation. We proposed that the intracellular B30.2 domain of BTN3A1 binds prenyl pyrophosphates, resulting in a change in the extracellular BTN3A1 dimer that is detected by Vγ2Vδ2 TCRs. Such B30.2 binding was demonstrated recently. However, other investigators reported that the extracellular BTN3A1 IgV domain binds prenyl pyrophosphates, leading to the proposal that the Vγ2Vδ2 TCR recognizes the complex. To distinguish between these mechanisms, we mutagenized residues in the two binding sites and tested the mutant BTN3A1 proteins for their ability to mediate prenyl pyrophosphate stimulation of Vγ2Vδ2 T cells to proliferate and secrete TNF-α. Mutagenesis of residues in the IgV site had no effect on Vγ2Vδ2 T cell proliferation or secretion of TNF-α. In contrast, mutagenesis of residues within the basic pocket and surrounding V regions of the B30.2 domain abrogated prenyl pyrophosphate-induced proliferation. Mutations of residues making hydrogen bonds to the pyrophosphate moiety also abrogated TNF-α secretion, as did mutation of aromatic residues making contact with the alkenyl chain. Some mutations further from the B30.2 binding site also diminished stimulation, suggesting that the B30.2 domain may interact with a second protein. These findings support intracellular sensing of prenyl pyrophosphates by BTN3A1 rather than extracellular presentation. PMID:26475929

  16. Evolutionary comparison of prenylation pathway in kinetoplastid Leishmania and its sister Leptomonas.

    Science.gov (United States)

    Chauhan, Indira Singh; Kaur, Jaspreet; Krishna, Shagun; Ghosh, Arpita; Singh, Prashant; Siddiqi, Mohammad Imran; Singh, Neeloo

    2015-11-21

    presented in our present work has importance for drug design targeted to kill L. donovani in humans but not affect the human form of the prenylation enzymes.

  17. 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.

  18. Induction of prenylated isoflavonoids and stilbenoids in legumes

    NARCIS (Netherlands)

    Aisyah, S.

    2015-01-01

    The germination of legume seeds in the presence or absence of stress factors was studied with respect to compositional changes in prenylated isoflavonoids and stilbenoids. Different strategies were applied using (i) different types of legume seed, (ii) different stress factors i.e. biotic,

  19. 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.

  20. 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.

  1. Caged Protein Prenyltransferase Substrates: Tools for Understanding Protein Prenylation

    Energy Technology Data Exchange (ETDEWEB)

    DeGraw, Amanda J.; Hast, Michael A.; Xu, Juhua; Mullen, Daniel; Beese, Lorena S.; Barany, George; Distefano, Mark D. (Duke); (UMM)

    2010-11-15

    Originally designed to block the prenylation of oncogenic Ras, inhibitors of protein farnesyltransferase currently in preclinical and clinical trials are showing efficacy in cancers with normal Ras. Blocking protein prenylation has also shown promise in the treatment of malaria, Chagas disease and progeria syndrome. A better understanding of the mechanism, targets and in vivo consequences of protein prenylation are needed to elucidate the mode of action of current PFTase (Protein Farnesyltransferase) inhibitors and to create more potent and selective compounds. Caged enzyme substrates are useful tools for understanding enzyme mechanism and biological function. Reported here is the synthesis and characterization of caged substrates of PFTase. The caged isoprenoid diphosphates are poor substrates prior to photolysis. The caged CAAX peptide is a true catalytically caged substrate of PFTase in that it is to not a substrate, yet is able to bind to the enzyme as established by inhibition studies and X-ray crystallography. Irradiation of the caged molecules with 350 nm light readily releases their cognate substrate and their photolysis products are benign. These properties highlight the utility of those analogs towards a variety of in vitro and in vivo applications.

  2. 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

  3. 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

  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. Pharmacological profile of Xanthohumol, a Prenylated Flavonoid from Hops (Humulus lupulus)

    DEFF Research Database (Denmark)

    Liu, Ming; Hansen, Poul Erik; Wang, Genzhu

    2015-01-01

    The female inflorescences of hops (Humulus lupulus L.), a well-known bittering agent used in the brewing industry, have long been used in traditional medicines. Xanthohumol (XN) is one of the bioactive substances contributing to its medical applications. Among foodstuffs XN is found primarily in ...

  6. Protein Prenylation Constitutes an Endogenous Brake on Axonal Growth

    Directory of Open Access Journals (Sweden)

    Hai Li

    2016-07-01

    Full Text Available Suboptimal axonal regeneration contributes to the consequences of nervous system trauma and neurodegenerative disease, but the intrinsic mechanisms that regulate axon growth remain unclear. We screened 50,400 small molecules for their ability to promote axon outgrowth on inhibitory substrata. The most potent hits were the statins, which stimulated growth of all mouse- and human-patient-derived neurons tested, both in vitro and in vivo, as did combined inhibition of the protein prenylation enzymes farnesyltransferase (PFT and geranylgeranyl transferase I (PGGT-1. Compensatory sprouting of motor axons may delay clinical onset of amyotrophic lateral sclerosis (ALS. Accordingly, elevated levels of PGGT1B, which would be predicted to reduce sprouting, were found in motor neurons of early- versus late-onset ALS patients postmortem. The mevalonate-prenylation pathway therefore constitutes an endogenous brake on axonal growth, and its inhibition provides a potential therapeutic approach to accelerate neuronal regeneration in humans.

  7. Inhibition of prenylated KRAS in a lipid environment.

    Directory of Open Access Journals (Sweden)

    Johanna M Jansen

    Full Text Available RAS mutations lead to a constitutively active oncogenic protein that signals through multiple effector pathways. In this chemical biology study, we describe a novel coupled biochemical assay that measures activation of the effector BRAF by prenylated KRASG12V in a lipid-dependent manner. Using this assay, we discovered compounds that block biochemical and cellular functions of KRASG12V with low single-digit micromolar potency. We characterized the structural basis for inhibition using NMR methods and showed that the compounds stabilized the inactive conformation of KRASG12V. Determination of the biophysical affinity of binding using biolayer interferometry demonstrated that the potency of inhibition matches the affinity of binding only when KRAS is in its native state, namely post-translationally modified and in a lipid environment. The assays we describe here provide a first-time alignment across biochemical, biophysical, and cellular KRAS assays through incorporation of key physiological factors regulating RAS biology, namely a negatively charged lipid environment and prenylation, into the in vitro assays. These assays and the ligands we discovered are valuable tools for further study of KRAS inhibition and drug discovery.

  8. Statins and protein prenylation in cancer cell biology and therapy.

    Science.gov (United States)

    Garcia-Ruiz, Carmen; Morales, Albert; Fernandez-Checa, Jose C

    2012-05-01

    The use of statins has scaled up to become one of the most prescribed medicines in the world and have been very useful in the manegement of cardiovascular diseases and related mortality. The disclosure of their chemical structure similar to that of hydroxy methyl glutaryl-CoA (HMG-CoA) revealed their ability to compete with and inhibit the rate-limiting enzyme HMG-CoA reductase that catalyzes the synthesis of mevalonate, which then serves as the precursor for isoprenoids and cholesterol in the mevalonate pathway. While most of the effects of statins are associated with the lowering of cellular cholesterol levels, it is clear that they also blunt the non-sterol branch of the mevalonate pathway, decreasing formation of isoprenoids and altering protein-prenylation, a critical event in the posttranslational modulation of proteins involved in the regulation of cell cycle progression, proliferation and signaling pathways. Randomized controlled trials for the prevention of cardiovascular diseases indicated that statins elicited provocative and unexpected benefits for reducing a number of different types of cancers, including colorectal carcinoma, melanoma, prostate and hepatocellular carcinoma, although in other cancer types the preclinical expectations of statins were dissapointing. In this review, we will describe the evidence and mechanisms underlying the potential beneficial use of statins and the role of protein prenylation in cancer prevention. Of relevance, the combination of statins with other anti cancer drugs may be a significant asset in malignancies resistant to current therapy.

  9. A natural flavonoid present in unripe plantain banana pulp (Musa sapientum L. var. paradisiaca) protects the gastric mucosa from aspirin-induced erosions.

    Science.gov (United States)

    Lewis, D A; Fields, W N; Shaw, G P

    1999-06-01

    The active anti-ulcerogenic ingredient was extracted from unripe plantain banana by solvent fractionation and identified by chromatography, spectroscopy and high performance liquid chromatography as the flavonoid leucocyanidin. Dried unripe plantain banana powder, the extracted leucocyanidin and a purified synthetic leucocyanidin demonstrated a significant (P < 0.05) protective effect against aspirin-induced erosions.

  10. Prenylated Polyphenols from Clusiaceae and Calophyllaceae with Immunomodulatory Activity on Endothelial Cells.

    Science.gov (United States)

    Rouger, Caroline; Pagie, Sylvain; Derbré, Séverine; Le Ray, Anne-Marie; Richomme, Pascal; Charreau, Béatrice

    2016-01-01

    Endothelial cells (ECs) are key players in inflammation and immune responses involved in numerous pathologies. Although attempts were experimentally undertaken to prevent and control EC activation, drug leads and probes still remain necessary. Natural products (NPs) from Clusiaceous and Calophyllaceous plants were previously reported as potential candidates to prevent endothelial dysfunction. The present study aimed to identify more precisely the molecular scaffolds that could limit EC activation. Here, 13 polyphenols belonging to 5 different chemical types of secondary metabolites (i.e., mammea coumarins, a biflavonoid, a pyranochromanone acid, a polyprenylated polycyclic acylphloroglucinol (PPAP) and two xanthones) were tested on resting and cytokine-activated EC cultures. Quantitative and qualitative changes in the expression of both adhesion molecules (VCAM-1, ICAM-1, E-selectin) and major histocompatibility complex (MHC) molecules have been used to measure their pharmaceutical potential. As a result, we identified 3 mammea coumarins that efficiently reduce (up to >90% at 10 μM) both basal and cytokine-regulated levels of MHC class I, class II, MICA and HLA-E on EC surface. They also prevented VCAM-1 induction upon inflammation. From a structural point of view, our results associate the loss of the free prenyl group substituting mammea coumarins with a reduced cellular cytotoxicity but also an abrogation of their anti-inflammatory potential and a reduction of their immunosuppressive effects. A PPAP, guttiferone J, also triggers a strong immunomodulation but restricted to HLA-E and MHC class II molecules. In conclusion, mammea coumarins with a free prenyl group and the PPAP guttiferone J emerge as NPs able to drastically decrease both VCAM-1 and a set of MHC molecules and to potentially reduce the immunogenicity of the endothelium.

  11. Prenylated Polyphenols from Clusiaceae and Calophyllaceae with Immunomodulatory Activity on Endothelial Cells.

    Directory of Open Access Journals (Sweden)

    Caroline Rouger

    Full Text Available Endothelial cells (ECs are key players in inflammation and immune responses involved in numerous pathologies. Although attempts were experimentally undertaken to prevent and control EC activation, drug leads and probes still remain necessary. Natural products (NPs from Clusiaceous and Calophyllaceous plants were previously reported as potential candidates to prevent endothelial dysfunction. The present study aimed to identify more precisely the molecular scaffolds that could limit EC activation. Here, 13 polyphenols belonging to 5 different chemical types of secondary metabolites (i.e., mammea coumarins, a biflavonoid, a pyranochromanone acid, a polyprenylated polycyclic acylphloroglucinol (PPAP and two xanthones were tested on resting and cytokine-activated EC cultures. Quantitative and qualitative changes in the expression of both adhesion molecules (VCAM-1, ICAM-1, E-selectin and major histocompatibility complex (MHC molecules have been used to measure their pharmaceutical potential. As a result, we identified 3 mammea coumarins that efficiently reduce (up to >90% at 10 μM both basal and cytokine-regulated levels of MHC class I, class II, MICA and HLA-E on EC surface. They also prevented VCAM-1 induction upon inflammation. From a structural point of view, our results associate the loss of the free prenyl group substituting mammea coumarins with a reduced cellular cytotoxicity but also an abrogation of their anti-inflammatory potential and a reduction of their immunosuppressive effects. A PPAP, guttiferone J, also triggers a strong immunomodulation but restricted to HLA-E and MHC class II molecules. In conclusion, mammea coumarins with a free prenyl group and the PPAP guttiferone J emerge as NPs able to drastically decrease both VCAM-1 and a set of MHC molecules and to potentially reduce the immunogenicity of the endothelium.

  12. Synthesis of the naturally occurring prenylated coumarins balsamiferone and cedrelopsin by domino reactions

    Digital Repository Service at National Institute of Oceanography (India)

    Patre, R.E.; Parameswaran, P.S.; Tilve, S.G.

    Regioselective one step synthesis of naturally occurring prenyl coumarin balsamiferone is described using domino Wittig reaction, 3,3-sigmatropic rearrangements and deprenylation, while regioselective synthesis of cedrelopsin is described via domino...

  13. A New Prenylated Xanthone from Latex of Garcinia cowa Roxb.

    Directory of Open Access Journals (Sweden)

    Zhi Na

    2013-05-01

    Full Text Available A new prenylated xanthone, 1,6-dihydroxy-3,7-dimethoxy-2-(3,7-dimethyloct-2,6-dienyl xanthone (3-O-methylcowaxanthone (1, together with four known xanthones, cowaxanthone (2, 7-O-methylgarcinone (3, α-mangostin (4 and γ-mangostin (5 were isolated from the latex of Garcinia cowa. The structure of compound 1 was elucidated on the basis of spectroscopic data interpretation, including 1D and 2D NMR and HREIMS. The cytotoxic activitiy of 1 against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7 and SW480, was evaluated, but it was inactive (IC 50>40μM.

  14. 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.

  15. 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

  16. Protective effects of flavonoids from corn silk on oxidative stress ...

    African Journals Online (AJOL)

    Protective effects of flavonoids from corn silk on oxidative stress induced by ... The present study aims at exploring the effects of flavonoids from corn silk (FCS) on oxidative stress induced by exhaustive exercise in mice. ... from 32 Countries:.

  17. Prenylated Chalcone 2 Acts as an Antimitotic Agent and Enhances the Chemosensitivity of Tumor Cells to Paclitaxel

    Directory of Open Access Journals (Sweden)

    Joana Fonseca

    2016-07-01

    Full Text Available We previously reported that prenylated chalcone 2 (PC2, the O-prenyl derivative (2 of 2′-hydroxy-3,4,4′,5,6′-pentamethoxychalcone (1, induced cytotoxicity of tumor cells via disruption of p53-MDM2 interaction. However, the cellular changes through which PC2 exerts its cytotoxic activity and its antitumor potential, remain to be addressed. In the present work, we aimed to (i characterize the effect of PC2 on mitotic progression and the underlying mechanism; and to (ii explore this information to evaluate its ability to sensitize tumor cells to paclitaxel in a combination regimen. PC2 was able to arrest breast adenocarcinoma MCF-7 and non-small cell lung cancer NCI-H460 cells in mitosis. All mitosis-arrested cells showed collapsed mitotic spindles with randomly distributed chromosomes, and activated spindle assembly checkpoint. Live-cell imaging revealed that the compound induced a prolonged delay (up to 14 h in mitosis, culminating in massive cell death by blebbing. Importantly, PC2 in combination with paclitaxel enhanced the effect on cell growth inhibition as determined by cell viability and proliferation assays. Our findings demonstrate that the cytotoxicity induced by PC2 is mediated through antimitotic activity as a result of mitotic spindle damage. The enhancement effects of PC2 on chemosensitivity of cancer cells to paclitaxel encourage further validation of the clinical potential of this combination.

  18. 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

  19. Marine natural flavonoids: chemistry and biological activities.

    Science.gov (United States)

    Martins, Beatriz T; Correia da Silva, Marta; Pinto, Madalena; Cidade, Honorina; Kijjoa, Anake

    2018-05-04

    As more than 70% of the world's surface is covered by oceans, marine organisms offer a rich and unlimited resource of structurally diverse bioactive compounds. These organisms have developed unique properties and bioactive compounds that are, in majority of them, unparalleled by their terrestrial counterparts due to the different surrounding ecological systems. Marine flavonoids have been extensively studied in the last decades due to a growing interest concerning their promising biological/pharmacological activities. The most common classes of marine flavonoids are flavones and flavonols, which are mostly isolated from marine plants. Although most of flavonoids are hydroxylated and methoxylated, some marine flavonoids possess an unusual substitution pattern, not commonly found in terrestrial organisms, namely the presence of sulphate, chlorine, and amino groups. This review presents, for the first time in a systematic way, the structure, natural occurrence, and biological activities of marine flavonoids.

  20. Circadian rhythm of anti-fungal prenylated chromene in leaves of Piper aduncum.

    Science.gov (United States)

    Morandim, Andreia de A; Bergamo, Débora Cristina B; Kato, Massuo Jorge; Cavalheiro, Alberto José; Bolzani, Vanderlan da S; Furlan, Maysa

    2005-01-01

    Leaves of Piper aduncum accumulate the anti-fungal chromenes methyl 2,2-dimethyl-2H-1-chromene-6-carboxylate (1) and methyl 2,2-dimethyl-8-(3'-methyl-2'-butenyl)-2H-1-chromene-6-carboxylate (2). The enzymatic formation of 2 from dimethylallyl diphosphate and 1 was investigated using cell-free extracts of the title plant. An HPLC assay for the prenylation reaction was developed and the enzyme activity measured in the protein extracts. The prenyltransferase that catalyses the transfer of the dimethylallyl group to C-2' of 1 was soluble and required dimethylallyl diphosphate as the prenyl donor. In the leaves, the biosynthesis of the prenylated chromene 2 was time-regulated and prenyltransferase activity depended upon circadian variation. Preliminary characterisation and purification experiments on the prenyltransferase from P. aduncum have been performed.

  1. Various oils and detergents enhance the microbial production of farnesol and related prenyl alcohols.

    Science.gov (United States)

    Muramatsu, Masayoshi; Ohto, Chikara; Obata, Shusei; Sakuradani, Eiji; Shimizu, Sakayu

    2008-09-01

    The object of this research was improvement of prenyl alcohol production with squalene synthase-deficient mutant Saccharomyces cerevisiae ATCC 64031. On screening of many kinds of additives, we found that oils and detergents significantly enhanced the extracellular production of prenyl alcohols. Soybean oil showed the most prominent effect among the additives tested. Its effect was accelerated by a high concentration of glucose in the medium. The combination of these cultivation conditions led to the production of more than 28 mg/l of farnesol in the soluble fraction of the broth. The addition of these compounds to the medium was an effective method for large-scale production of prenyl alcohols with microorganisms.

  2. Microbial production of natural and non-natural flavonoids: Pathway engineering, directed evolution and systems/synthetic biology.

    Science.gov (United States)

    Pandey, Ramesh Prasad; Parajuli, Prakash; Koffas, Mattheos A G; Sohng, Jae Kyung

    2016-01-01

    In this review, we address recent advances made in pathway engineering, directed evolution, and systems/synthetic biology approaches employed in the production and modification of flavonoids from microbial cells. The review is divided into two major parts. In the first, various metabolic engineering and system/synthetic biology approaches used for production of flavonoids and derivatives are discussed broadly. All the manipulations/engineering accomplished on the microorganisms since 2000 are described in detail along with the biosynthetic pathway enzymes, their sources, structures of the compounds, and yield of each product. In the second part of the review, post-modifications of flavonoids by four major reactions, namely glycosylations, methylations, hydroxylations and prenylations using recombinant strains are described. Copyright © 2016 Elsevier Inc. All rights reserved.

  3. Mass Spectrometric Characteristics of Prenylated Indole Derivatives from Marine-Derived Penicillium sp. NH-SL.

    Science.gov (United States)

    Ding, Hui; Ding, Wanjing; Ma, Zhongjun

    2017-03-22

    Two prenylated indole alkaloids were isolated from the ethyl acetate extracts of a marine-derived fungus Penicillium sp. NH-SL and one of them exhibited potent cytotoxic activity against mouse hepa 1c1c7 cells. In order to detect other bioactive analogs, we used liquid chromatogram tandem mass spectrometry (LC-MS/MS) to analyze the mass spectrometric characteristics of the isolated compounds as well as the crude extracts. As a result, three other analogs were detected, and their structures were deduced according to the similar fragmentation patterns. This is the first systematic report on the mass spectrometric characteristics of prenylated indole derivatives.

  4. Diurnal changes in flavonoids

    International Nuclear Information System (INIS)

    Veit, M.; Bilger, W.; Mühlbauer, T.; Brummet, W.; Winter, K.

    1996-01-01

    Field studies of a tropical tree, Anacardium excelsum, and a northern hemisphere high altitude fern, Cryptogramma crispa, revealed marked diurnal changes in soluble flavonoid content of leaves and fronds, respectively. The flavonoid content increased during the morning and decreased during the afternoon. In plants of C. crispa covered with UV-B absorbing filters, the flavonoid content remained at a constant level throughout the day/night cycle. Upon removal of UV-B absorbing filters (at night), the flavonoid content increased the next morning in a fashion similar to that observed in control plants maintained without filters. Decreases in photosystem II photochemical efficiency upon exposure of C. crispa to natural daylight were similar in plants previously covered with UV-B absorbing filters and in control plants, probably owing to the observed ability of plants to rapidly accumulate UV-B protective flavonoids. (author)

  5. Prenylated isoflavonoids from soya and licorice : analysis, induction and in vitro estrogenicity

    NARCIS (Netherlands)

    Simons, R.

    2011-01-01


    Prenylatedisoflavonoids are found in large amountsin soya bean (Glycine max) germinated under stress and in licorice (Glycyrrhiza glabra). Prenylation of isoflavonoids has been associated with modification of theirestrogenic activity.
    The aims of this thesis were (1) to provide a

  6. Design, synthesis, and biological evaluation of prenylated chalcones as 5-LOX inhibitors.

    Science.gov (United States)

    Reddy, Nimmanapalli P; Aparoy, Polamarasetty; Reddy, T Chandra Mohan; Achari, Chandrani; Sridhar, P Ramu; Reddanna, Pallu

    2010-08-15

    Ten novel mono- and di-O-prenylated chalcone derivatives were designed on the basis of a homology derived molecular model of 5-lipoxygenase (5-LOX). The compounds were docked into 5-LOX active site and the binding characteristics were quantified using LUDI. To verify our theoretical assumption, the molecules were synthesized and tested for their 5-LOX inhibitory activities. The synthesis was carried out by Claisen-Schmidt condensation reaction of mono- and di-O-prenylated acetophenones with appropriate aldehydes. 5-LOX in vitro inhibition assay showed higher potency of di-O-prenylated chalcones than their mono-O-prenylated chalcone analogs. Compound 5e exhibited good inhibition with an IC(50) at 4 microM. The overall trend for the binding energies calculated and LUDI score was in good qualitative agreement with the experimental data. Further, the compound 5e showed potent anti-proliferative effects (GI(50) at 9 microM) on breast cancer cell line, MCF-7. Copyright 2010 Elsevier Ltd. All rights reserved.

  7. Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)

    DEFF Research Database (Denmark)

    Kagiyama, Ippei; Kato, Hikaru; Nehira, Tatsuo

    2016-01-01

    Seven new prenylated indole alkaloids, taichunamides A–G, were isolated from the fungus Aspergillus taichungensis (IBT 19404). Taichunamides A and B contained an azetidine and 4‐pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)‐6‐epi‐stephacidin A. Taichunamides...... these cores within the three species likely arise from an intramolecular hetero Diels–Alder reaction....

  8. Biotransformation of menadione to its prenylated derivative MK-3 using recombinant Pichia pastoris.

    Science.gov (United States)

    Li, Zhemin; Zhao, Genhai; Liu, Hui; Guo, Yugang; Wu, Hefang; Sun, Xiaowen; Wu, Xihua; Zheng, Zhiming

    2017-07-01

    Prenylated quinones, especially menaquinones, have significant physiological activities, but are arduous to synthesize efficiently. Due to the relaxed aromatic substrate specificity and prenylation regiospecificity at the ortho- site of the phenolic hydroxyl group, the aromatic prenyltransferase NovQ from Streptomyces may be useful in menaquinone synthesis from menadione. In this study, NovQ was overexpressed in Pichia pastoris. After fermentation optimization, NovQ production increased by 1617%. Then the different effects of metal ions, detergents and pH on the activity of purified NovQ were investigated to optimize the prenylation reaction. Finally, purified NovQ and cells containing NovQ were used for menadione prenylation in vitro and in vivo, respectively. Menaquinone-1 (MK-1) was detected as the only product in vitro with γ,γ-dimethylallyl pyrophosphate and menadione hydroquinol substrates. MK-3 at a concentration of 90.53 mg/L was detected as the major product of whole cell catalysis with 3-methyl-2-buten-1-ol and menadione hydroquinol substrates. This study realized whole cell catalysis converting menadione to menaquinones.

  9. The bisphosphonate zoledronic acid effectively targets lung cancer cells by inhibition of protein prenylation

    International Nuclear Information System (INIS)

    Xie, Fan; Li, Pengcheng; Gong, Jianhua; Zhang, Jiahong; Ma, Jingping

    2015-01-01

    Aberrant activation of oncoproteins such as members of the Ras family is common in human lung cancers. The proper function of Ras largely depends on a post-translational modification termed prenylation. Bisphosphonates have been shown to inhibit prenylation in cancer cells. In this study, we show that zoledronic acid, a third generation bisphosphonate, is effective in targeting lung cancer cells. This is achieved by the induction of apoptosis and inhibition of proliferation, through suppressing the activation of downstream Ras and EGFR signalling by zoledronic acid. The combination of zoledronic acid and paclitaxel or cisplatin (commonly used chemotherapeutic drugs for lung cancer) augmented the activity of either drug alone in in vitro lung cancer cellular system and in vivo lung xenograft mouse model. Importantly, zoledronic acid inhibits protein prenylation as shown by the increased levels of unprenylated Ras and Rap1A. In addition, the effects of zoledronic acid were reversed in the presence of geranylgeraniol and farnesol, further confirming that mechanism of zoledroinc acid's action in lung cancer cells is through prenylation inhibition. Since zoledronic acid is already available for clinic use, these results suggest that it may be an effective addition to the armamentarium of drugs for the treatment of lung cancer. - Highlights: • Zoledronic acid (ZA) is effectively against lung cancer cells in vitro and in vivo. • ZA acts on lung cancer cells through inhibition of protein prenylation. • ZA suppresses global downstream phosphorylation of Ras signalling. • ZA enhances the effects of chemotherapeutic drugs in lung cancer cells.

  10. The bisphosphonate zoledronic acid effectively targets lung cancer cells by inhibition of protein prenylation

    Energy Technology Data Exchange (ETDEWEB)

    Xie, Fan [Department of Respiratory Medicine, Jingzhou Hospital, Tongji Medical College, Huazhong University of Science and Technology (HUST), Jingzhou (China); Li, Pengcheng [Department of Oncology, Wuhan Union Hospital Affiliated to Huazhong University of Science and Technology, Wuhan (China); Gong, Jianhua; Zhang, Jiahong [Department of Respiratory Medicine, Jingzhou Hospital, Tongji Medical College, Huazhong University of Science and Technology (HUST), Jingzhou (China); Ma, Jingping, E-mail: mjpjzhospital@hotmail.com [Department of Respiratory Medicine, Jingzhou Hospital, Tongji Medical College, Huazhong University of Science and Technology (HUST), Jingzhou (China)

    2015-11-27

    Aberrant activation of oncoproteins such as members of the Ras family is common in human lung cancers. The proper function of Ras largely depends on a post-translational modification termed prenylation. Bisphosphonates have been shown to inhibit prenylation in cancer cells. In this study, we show that zoledronic acid, a third generation bisphosphonate, is effective in targeting lung cancer cells. This is achieved by the induction of apoptosis and inhibition of proliferation, through suppressing the activation of downstream Ras and EGFR signalling by zoledronic acid. The combination of zoledronic acid and paclitaxel or cisplatin (commonly used chemotherapeutic drugs for lung cancer) augmented the activity of either drug alone in in vitro lung cancer cellular system and in vivo lung xenograft mouse model. Importantly, zoledronic acid inhibits protein prenylation as shown by the increased levels of unprenylated Ras and Rap1A. In addition, the effects of zoledronic acid were reversed in the presence of geranylgeraniol and farnesol, further confirming that mechanism of zoledroinc acid's action in lung cancer cells is through prenylation inhibition. Since zoledronic acid is already available for clinic use, these results suggest that it may be an effective addition to the armamentarium of drugs for the treatment of lung cancer. - Highlights: • Zoledronic acid (ZA) is effectively against lung cancer cells in vitro and in vivo. • ZA acts on lung cancer cells through inhibition of protein prenylation. • ZA suppresses global downstream phosphorylation of Ras signalling. • ZA enhances the effects of chemotherapeutic drugs in lung cancer cells.

  11. 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.

  12. The position of prenylation of isoflavonoids and stilbenoids from legumes (Fabaceae) modulates the antimicrobial activity against Gram positive pathogens.

    Science.gov (United States)

    Araya-Cloutier, Carla; den Besten, Heidy M W; Aisyah, Siti; Gruppen, Harry; Vincken, Jean-Paul

    2017-07-01

    The legume plant family (Fabaceae) is a potential source of antimicrobial phytochemicals. Molecular diversity in phytochemicals of legume extracts was enhanced by germination and fungal elicitation of seven legume species, as established by RP-UHPLC-UV-MS. The relationship between phytochemical composition, including different types of skeletons and substitutions, and antibacterial properties of extracts was investigated. Extracts rich in prenylated isoflavonoids and stilbenoids showed potent antibacterial activity against Listeria monocytogenes and methicillin-resistant Staphylococcus aureus at concentrations between 0.05 and 0.1% (w/v). Prenylated phenolic compounds were significantly (p<0.01) correlated with the antibacterial properties of the extracts. Furthermore, the position of the prenyl group within the phenolic skeleton also influenced the antibacterial activity. Overall, prenylated phenolics from legume seedlings can serve multiple purposes, e.g. as phytoestrogens they can provide health benefits and as natural antimicrobials they offer preservation of foods. Copyright © 2017 Elsevier Ltd. All rights reserved.

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

    OpenAIRE

    Md. Shafiullah Shajib; Bidyut Kanti Datta; Md. Hossain Sohrab; Mohammad Abdur Rashid; Lutfun Nahar; Satyajit Dey Sarker

    2017-01-01

    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...

  14. 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.

  15. Isoprenoids responsible for protein prenylation modulate the biological effects of statins on pancreatic cancer cells

    Czech Academy of Sciences Publication Activity Database

    Gbelcová, H.; Rimpelová, S.; Knejzlík, Z.; Šáchová, Jana; Kolář, Michal; Strnad, Hynek; Repiska, V.; D'Acunto, C.W.; Ruml, T.; Vítek, L.

    2017-01-01

    Roč. 16, zima (2017), č. článku 250. ISSN 1476-511X R&D Projects: GA MZd(CZ) NT13112 Institutional support: RVO:68378050 Keywords : Farmesyl pyrophosphate * Gene expression * Geranylgeranyl pyrophosphate * HMG-CoA reductase inhibitors * Isoprenoids * K-Ras oncogene * Mevalonate * Pncreatic cancer * Prenylation * Statins Subject RIV: EB - Genetics ; Molecular Biology OBOR OECD: Cell biology Impact factor: 2.073, year: 2016

  16. Increased RhoA prenylation in the loechrig (loe mutant leads to progressive neurodegeneration.

    Directory of Open Access Journals (Sweden)

    Mandy Cook

    Full Text Available The Drosophila mutant loechrig (loe shows age-dependent degeneration of the nervous system and is caused by the loss of a neuronal isoform of the AMP-activated protein kinase (AMPK γ-subunit (also known as SNF4Aγ. The trimeric AMPK complex is activated by low energy levels and metabolic insults and regulates multiple important signal pathways that control cell metabolism. A well-known downstream target of AMPK is hydroxyl-methylglutaryl-CoA reductase (HMGR, a key enzyme in isoprenoid synthesis, and we have previously shown that HMGR genetically interacts with loe and affects the severity of the degenerative phenotype. Prenylation of proteins like small G-proteins is an important posttranslational modification providing lipid moieties that allow the association of these proteins with membranes, thereby facilitating their subsequent activation. Rho proteins have been extensively studied in neuronal outgrowth, however, much less is known about their function in neuronal maintenance. Here we show that the loe mutation interferes with isoprenoid synthesis, leading to increased prenylation of the small GTPase Rho1, the fly orthologue of vertebrate RhoA. We also demonstrate that increased prenylation and Rho1 activity causes neurodegeneration and aggravates the behavioral and degenerative phenotypes of loe. Because we cannot detect defects in the development of the central nervous system in loe, this suggests that loe only interferes with the function of the RhoA pathway in maintaining neuronal integrity during adulthood. In addition, our results show that alterations in isoprenoids can result in progressive neurodegeneration, supporting findings in vertebrates that prenylation may play a role in neurodegenerative diseases like Alzheimer's Disease.

  17. The prenyl-binding protein PrBP/δ: a chaperone participating in intracellular trafficking.

    Science.gov (United States)

    Zhang, Houbin; Constantine, Ryan; Frederick, Jeanne M; Baehr, Wolfgang

    2012-12-15

    Expressed ubiquitously, PrBP/δ functions as chaperone/co-factor in the transport of a subset of prenylated proteins. PrBP/δ features an immunoglobulin-like β-sandwich fold for lipid binding, and interacts with diverse partners. PrBP/δ binds both C-terminal C15 and C20 prenyl side chains of phototransduction polypeptides and small GTP-binding (G) proteins of the Ras superfamily. PrBP/δ also interacts with the small GTPases, ARL2 and ARL3, which act as release factors (GDFs) for prenylated cargo. Targeted deletion of the mouse Pde6d gene encoding PrBP/δ resulted in impeded trafficking to the outer segments of GRK1 and cone PDE6 which are predicted to be farnesylated and geranylgeranylated, respectively. Rod and cone transducin trafficking was largely unaffected. These trafficking defects produce progressive cone-rod dystrophy in the Pde6d(-/-) mouse. Copyright © 2012 Elsevier Ltd. All rights reserved.

  18. 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

  19. 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.

  20. Inhibiting prenylation augments chemotherapy efficacy in renal cell carcinoma through dual inhibition on mitochondrial respiration and glycolysis.

    Science.gov (United States)

    Huang, Jiangrong; Yang, Xiaoyu; Peng, Xiaochun; Huang, Wei

    2017-11-18

    Prenylation is a posttranslational lipid modification required for the proper functions of a number of proteins involved in cell regulation. Here, we show that prenylation inhibition is important for renal cell carcinoma (RCC) growth, survival and response to chemotherapy, and its underlying mechanism may be contributed to mitochondrial dysfunction. We first demonstrated that a HMG-CoA reductase inhibitor pitavastatin inhibited mevalonate pathway and thereby prenylation in RCC cells. In addition, pitavastatin is effective in inhibiting growth and inducing apoptosis in a panel of RCC cell lines. Combination of pitavastatin and paclitaxel is significantly more effective than pitavastatin or paclitaxel alone as shown by both in vitro cell culture system and in vivo RCC xenograft model. Importantly, pitavastatin treatment inhibits mitochondrial respiration via suppressing mitochondrial complex I and II enzyme activities. Interestingly, different from mitochondrial inhibitor phenformin that inhibits mitochondrial respiration but activates glycolytic rate in RCC cells, pitavastatin significantly decreases glycolytic rate. The dual inhibitory action of pitavastatin on mitochondrial respiration and glycolysis results in remarkable energy depletion and oxidative stress in RCC cells. In addition, inhibition of prenylation by depleting Isoprenylcysteine carboxylmethyltransferase (Icmt) also mimics the inhibitory effects of pitavastatin in RCC cells. Our work demonstrates the previously unappreciated association between prenylation inhibition and energy metabolism in RCC, which can be therapeutically exploited, likely in tumors that largely rely on energy metabolism. Copyright © 2017 Elsevier Inc. All rights reserved.

  1. 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

  2. Presentations

    International Nuclear Information System (INIS)

    2007-01-01

    The presented materials consist of presentations of international workshop which held in Warsaw from 4 to 5 October 2007. Main subject of the meeting was progress in manufacturing as well as research program development for neutron detector which is planned to be placed at GANIL laboratory and will be used in nuclear spectroscopy research

  3. The root barks of Morus alba and the flavonoid constituents inhibit airway inflammation.

    Science.gov (United States)

    Lim, Hun Jai; Jin, Hong-Guang; Woo, Eun-Rhan; Lee, Sang Kook; Kim, Hyun Pyo

    2013-08-26

    The root barks of Morus alba have been used in traditional medicine as an anti-inflammatory drug, especially for treating lung inflammatory disorders. To find new alternative agents against airway inflammation and to establish the scientific rationale of the herbal medicine in clinical use, the root barks of Morus alba and its flavonoid constituents were examined for the first time for their pharmacological activity against lung inflammation. For in vivo evaluation, an animal model of lipopolysaccharide-induced airway inflammation in mice was used. An inhibitory action against the production of proinflammatory molecules in lung epithelial cells and lung macrophages was examined. Against lipopolysaccharide-induced airway inflammation, the ethanol extract of the root barks of Morus alba clearly inhibited bronchitis-like symptoms, as determined by TNF-α production, inflammatory cells infiltration and histological observation at 200-400mg/kg/day by oral administration. In addition, Morus alba and their major flavonoid constituents including kuwanone E, kuwanone G and norartocarpanone significantly inhibited IL-6 production in lung epithelial cells (A549) and NO production in lung macrophages (MH-S). Taken together, it is concluded that Morus alba and the major prenylated flavonoid constituents have a potential for new agents to control lung inflammation including bronchitis. Copyright © 2013 Elsevier Ireland Ltd. All rights reserved.

  4. Total phenolics and total flavonoids in selected Indian medicinal plants.

    Science.gov (United States)

    Sulaiman, C T; Balachandran, Indira

    2012-05-01

    Plant phenolics and flavonoids have a powerful biological activity, which outlines the necessity of their determination. The phenolics and flavonoids content of 20 medicinal plants were determined in the present investigation. The phenolic content was determined by using Folin-Ciocalteu assay. The total flavonoids were measured spectrophotometrically by using the aluminium chloride colorimetric assay. The results showed that the family Mimosaceae is the richest source of phenolics, (Acacia nilotica: 80.63 mg gallic acid equivalents, Acacia catechu 78.12 mg gallic acid equivalents, Albizia lebbeck 66.23 mg gallic acid equivalents). The highest total flavonoid content was revealed in Senna tora which belongs to the family Caesalpiniaceae. The present study also shows the ratio of flavonoids to the phenolics in each sample for their specificity.

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

    OpenAIRE

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

    2011-01-01

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

  6. 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.

  7. Flavonoids of Steganotaenia araliacea

    CSIR Research Space (South Africa)

    Omolo, JJ

    2014-01-01

    Full Text Available Communication www.usa-journals.com Omolo, et al., 2014: Vol 2(8) 52 ajrc.journal@gmail.com Flavonoids of Steganotaenia araliacea 1,2,3*Omolo J.J., 2Maharaj V., 2... Communication www.usa-journals.com Omolo, et al., 2014: Vol 2(8) 53 ajrc.journal@gmail.com Introduction The Tanga Aids Working Group (TAWG) in collaboration...

  8. Presentations

    International Nuclear Information System (INIS)

    2007-01-01

    The PARIS meeting held in Cracow, Poland from 14 to 15 May 2007. The main subjects discussed during this meeting were the status of international project dedicated to gamma spectroscopy research. The scientific research program includes investigations of giant dipole resonance, probe of hot nuclei induced in heavy reactions, Jacobi shape transitions, isospin mixing and nuclear multifragmentation. The mentioned programme needs Rand D development such as new scintillations materials as lanthanum chlorides and bromides as well as new photo detection sensors as avalanche photodiodes - such subjects are also subjects of discussion. Additionally results of computerized simulations of scintillation detectors properties by means of GEANT- 4 code are presented

  9. Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata

    Directory of Open Access Journals (Sweden)

    Xiang-Mei Li

    2016-09-01

    Full Text Available Abstract Four hitherto unknown prenylated coumarins, namely 6″-O-β-d-apiofuranosylapterin (1, 4′-O-isobutyroylpeguangxienin (2, 6-(3-methyl-2-oxobutyroyl-7-methoxycoumarin (3, and 6-hydroxycoumurrayin (4, were isolated from the ethanol extract of Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata, respectively. Their chemical structures were established on the basis of extensive spectroscopic analysis. Compound 2 exhibited in vitro cytotoxic activity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480 with IC50 values ranging from 15.9 to 23.2 μM. Graphical Abstract

  10. 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

  11. Presentation

    Directory of Open Access Journals (Sweden)

    Eduardo Vicente

    2013-06-01

    Full Text Available In the present edition of Significação – Scientific Journal for Audiovisual Culture and in the others to follow something new is brought: the presence of thematic dossiers which are to be organized by invited scholars. The appointed subject for the very first one of them was Radio and the invited scholar, Eduardo Vicente, professor at the Graduate Course in Audiovisual and at the Postgraduate Program in Audiovisual Media and Processes of the School of Communication and Arts of the University of São Paulo (ECA-USP. Entitled Radio Beyond Borders the dossier gathers six articles and the intention of reuniting works on the perspectives of usage of such media as much as on the new possibilities of aesthetical experimenting being build up for it, especially considering the new digital technologies and technological convergences. It also intends to present works with original theoretical approach and original reflections able to reset the way we look at what is today already a centennial media. Having broadened the meaning of “beyond borders”, four foreign authors were invited to join the dossier. This is the first time they are being published in this country and so, in all cases, the articles where either written or translated into Portuguese.The dossier begins with “Radio is dead…Long live to the sound”, which is the transcription of a thought provoking lecture given by Armand Balsebre (Autonomous University of Barcelona – one of the most influential authors in the world on the Radio study field. It addresses the challenges such media is to face so that it can become “a new sound media, in the context of a new soundscape or sound-sphere, for the new listeners”. Andrew Dubber (Birmingham City University regarding the challenges posed by a Digital Era argues for a theoretical approach in radio studies which can consider a Media Ecology. The author understands the form and discourse of radio as a negotiation of affordances and

  12. Site-directed Mutagenesis Switching a Dimethylallyl Tryptophan Synthase to a Specific Tyrosine C3-Prenylating Enzyme*

    Science.gov (United States)

    Fan, Aili; Zocher, Georg; Stec, Edyta; Stehle, Thilo; Li, Shu-Ming

    2015-01-01

    The tryptophan prenyltransferases FgaPT2 and 7-DMATS (7-dimethylallyl tryptophan synthase) from Aspergillus fumigatus catalyze C4- and C7-prenylation of the indole ring, respectively. 7-DMATS was found to accept l-tyrosine as substrate as well and converted it to an O-prenylated derivative. An acceptance of l-tyrosine by FgaPT2 was also observed in this study. Interestingly, isolation and structure elucidation revealed the identification of a C3-prenylated l-tyrosine as enzyme product. Molecular modeling and site-directed mutagenesis led to creation of a mutant FgaPT2_K174F, which showed much higher specificity toward l-tyrosine than l-tryptophan. Its catalytic efficiency toward l-tyrosine was found to be 4.9-fold in comparison with that of non-mutated FgaPT2, whereas the activity toward l-tryptophan was less than 0.4% of that of the wild-type. To the best of our knowledge, this is the first report on an enzymatic C-prenylation of l-tyrosine as free amino acid and altering the substrate preference of a prenyltransferase by mutagenesis. PMID:25477507

  13. 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.

  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. 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.

  16. Structure-activity relationship of prenyl-substituted polyphenols from Artocarpus heterophyllus as inhibitors of melanin biosynthesis in cultured melanoma cells.

    Science.gov (United States)

    Arung, Enos Tangke; Shimizu, Kuniyoshi; Kondo, Ryuichiro

    2007-09-01

    A series of prenylated, flavone-based polyphenols, compounds 1-8, were isolated from the wood of Artocarpus heterophyllus. These compounds, which have previously been shown not to inhibit tyrosinase activity, were found to be active inhibitors of the in vivo melanin biosynthesis in B16 melanoma cells, with little or no cytotoxicity. To clarify the structural requirement for inhibition, some structure-activity relationships were studied, in comparison with related compounds lacking prenyl side chains. Our experiments indicate that both prenyl and OH groups, as well as the type of substitution pattern, are crucial for the inhibition of melanin production in B16 melanoma cells.

  17. Quantitative and qualitative characteristics of cell wall components and prenyl lipids in the leaves of Tilia x euchlora trees growing under salt stress.

    Science.gov (United States)

    Milewska-Hendel, Anna; Baczewska, Aneta H; Sala, Katarzyna; Dmuchowski, Wojciech; Brągoszewska, Paulina; Gozdowski, Dariusz; Jozwiak, Adam; Chojnacki, Tadeusz; Swiezewska, Ewa; Kurczynska, Ewa

    2017-01-01

    The study was focused on assessing the presence of arabinogalactan proteins (AGPs) and pectins within the cell walls as well as prenyl lipids, sodium and chlorine content in leaves of Tilia x euchlora trees. The leaves that were analyzed were collected from trees with and without signs of damage that were all growing in the same salt stress conditions. The reason for undertaking these investigations was the observations over many years that indicated that there are trees that present a healthy appearance and trees that have visible symptoms of decay in the same habitat. Leaf samples were collected from trees growing in the median strip between roadways that have been intensively salted during the winter season for many years. The sodium content was determined using atomic spectrophotometry, chloride using potentiometric titration and poly-isoprenoids using HPLC/UV. AGPs and pectins were determined using immunohistochemistry methods. The immunohistochemical analysis showed that rhamnogalacturonans I (RG-I) and homogalacturonans were differentially distributed in leaves from healthy trees in contrast to leaves from injured trees. In the case of AGPs, the most visible difference was the presence of the JIM16 epitope. Chemical analyses of sodium and chloride showed that in the leaves from injured trees, the level of these ions was higher than in the leaves from healthy trees. Based on chromatographic analysis, four poly-isoprenoid alcohols were identified in the leaves of T. x euchlora. The levels of these lipids were higher in the leaves from healthy trees. The results suggest that the differences that were detected in the apoplast and symplasm may be part of the defensive strategy of T. x euchlora trees to salt stress, which rely on changes in the chemical composition of the cell wall with respect to the pectic and AGP epitopes and an increased synthesis of prenyl lipids.

  18. 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.

  19. Antiartherosclerotic Effects of Plant Flavonoids

    Directory of Open Access Journals (Sweden)

    Shamala Salvamani

    2014-01-01

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

  20. Flavonoid intake and all-cause mortality.

    Science.gov (United States)

    Ivey, Kerry L; Hodgson, Jonathan M; Croft, Kevin D; Lewis, Joshua R; Prince, Richard L

    2015-05-01

    Flavonoids are bioactive compounds found in foods such as tea, chocolate, red wine, fruit, 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 flavonoids in preventing all-cause mortality remains uncertain. The objective was to explore the association between flavonoid intake and risk of 5-y mortality from all causes by using 2 comprehensive food composition databases to assess flavonoid intake. The study population included 1063 randomly selected women aged >75 y. All-cause, cancer, and cardiovascular mortalities were assessed over 5 y of follow-up through the Western Australia Data Linkage System. Two estimates of flavonoid intake (total flavonoidUSDA and total flavonoidPE) were determined by using food composition data from the USDA and the Phenol-Explorer (PE) databases, respectively. During the 5-y follow-up period, 129 (12%) deaths were documented. Participants with high total flavonoid intake were at lower risk [multivariate-adjusted HR (95% CI)] of 5-y all-cause mortality than those with low total flavonoid consumption [total flavonoidUSDA: 0.37 (0.22, 0.58); total flavonoidPE: 0.36 (0.22, 0.60)]. Similar beneficial relations were observed for both cardiovascular disease mortality [total flavonoidUSDA: 0.34 (0.17, 0.69); flavonoidPE: 0.32 (0.16, 0.61)] and cancer mortality [total flavonoidUSDA: 0.25 (0.10, 0.62); flavonoidPE: 0.26 (0.11, 0.62)]. Using the most comprehensive flavonoid databases, we provide evidence that high consumption of flavonoids is associated with reduced risk of mortality in older women. The benefits of flavonoids may extend to the etiology of cancer and cardiovascular disease. © 2015 American Society for Nutrition.

  1. Flavonoids from Teucrium fruticans L.

    Directory of Open Access Journals (Sweden)

    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.

  2. A R2R3-MYB transcription factor from Epimedium sagittatum regulates the flavonoid biosynthetic pathway.

    Directory of Open Access Journals (Sweden)

    Wenjun Huang

    Full Text Available Herba epimedii (Epimedium, a traditional Chinese medicine, has been widely used as a kidney tonic and antirheumatic medicine for thousands of years. The bioactive components in herba epimedii are mainly prenylated flavonol glycosides, end-products of the flavonoid pathway. Epimedium species are also used as garden plants due to the colorful flowers and leaves. Many R2R3-MYB transcription factors (TFs have been identified to regulate the flavonoid and anthocyanin biosynthetic pathways. However, little is known about the R2R3-MYB TFs involved in regulation of the flavonoid pathway in Epimedium. Here, we reported the isolation and functional characterization of the first R2R3-MYB TF (EsMYBA1 from Epimedium sagittatum (Sieb. Et Zucc. Maxim. Conserved domains and phylogenetic analysis showed that EsMYBA1 belonged to the subgroup 6 clade (anthocyanin-related MYB clade of R2R3-MYB family, which includes Arabidopsis AtPAP1, apple MdMYB10 and legume MtLAP1. EsMYBA1 was preferentially expressed in leaves, especially in red leaves that contain higher content of anthocyanin. Alternative splicing of EsMYBA1 resulted in three transcripts and two of them encoded a MYB-related protein. Yeast two-hybrid and transient luciferase expression assay showed that EsMYBA1 can interact with several bHLH regulators of the flavonoid pathway and activate the promoters of dihydroflavonol 4-reductase (DFR and anthocyanidin synthase (ANS. In both transgenic tobacco and Arabidopsis, overexpression of EsMYBA1 induced strong anthocyanin accumulation in reproductive and/or vegetative tissues via up-regulation of the main flavonoid-related genes. Furthermore, transient expression of EsMYBA1 in E. sagittatum leaves by Agrobacterium infiltration also induced anthocyanin accumulation in the wounded area. This first functional characterization of R2R3-MYB TFs in Epimedium species will promote further studies of the flavonoid biosynthesis and regulation in medicinal plants.

  3. A R2R3-MYB transcription factor from Epimedium sagittatum regulates the flavonoid biosynthetic pathway.

    Science.gov (United States)

    Huang, Wenjun; Sun, Wei; Lv, Haiyan; Luo, Ming; Zeng, Shaohua; Pattanaik, Sitakanta; Yuan, Ling; Wang, Ying

    2013-01-01

    Herba epimedii (Epimedium), a traditional Chinese medicine, has been widely used as a kidney tonic and antirheumatic medicine for thousands of years. The bioactive components in herba epimedii are mainly prenylated flavonol glycosides, end-products of the flavonoid pathway. Epimedium species are also used as garden plants due to the colorful flowers and leaves. Many R2R3-MYB transcription factors (TFs) have been identified to regulate the flavonoid and anthocyanin biosynthetic pathways. However, little is known about the R2R3-MYB TFs involved in regulation of the flavonoid pathway in Epimedium. Here, we reported the isolation and functional characterization of the first R2R3-MYB TF (EsMYBA1) from Epimedium sagittatum (Sieb. Et Zucc.) Maxim. Conserved domains and phylogenetic analysis showed that EsMYBA1 belonged to the subgroup 6 clade (anthocyanin-related MYB clade) of R2R3-MYB family, which includes Arabidopsis AtPAP1, apple MdMYB10 and legume MtLAP1. EsMYBA1 was preferentially expressed in leaves, especially in red leaves that contain higher content of anthocyanin. Alternative splicing of EsMYBA1 resulted in three transcripts and two of them encoded a MYB-related protein. Yeast two-hybrid and transient luciferase expression assay showed that EsMYBA1 can interact with several bHLH regulators of the flavonoid pathway and activate the promoters of dihydroflavonol 4-reductase (DFR) and anthocyanidin synthase (ANS). In both transgenic tobacco and Arabidopsis, overexpression of EsMYBA1 induced strong anthocyanin accumulation in reproductive and/or vegetative tissues via up-regulation of the main flavonoid-related genes. Furthermore, transient expression of EsMYBA1 in E. sagittatum leaves by Agrobacterium infiltration also induced anthocyanin accumulation in the wounded area. This first functional characterization of R2R3-MYB TFs in Epimedium species will promote further studies of the flavonoid biosynthesis and regulation in medicinal plants.

  4. A quest for staunch effects of flavonoids: Utopian protection against hepatic ailments

    Directory of Open Access Journals (Sweden)

    Anju Dhiman

    2016-11-01

    Full Text Available The role of flavonoids as the major red, blue and purple pigments in plants has gained these secondary products a great deal of attention over the years. Flavonoids are polyphenols and occur as aglycones, glycosides and methylated derivatives. Flavonoids are the main components of a healthy diet containing fruits and vegetables and are concentrated especially in tea, apples and onions. Till date, more than 6000 flavonoids have been discovered, out of which 500 are found in free state. They are abundant in polygonaceae, rutaceae, leguminosae, umbelliferae and compositae. Flavonoids are powerful antioxidants. In addition to their role in nutrition, flavonoids possess many types of pharmacological activities, including anti-inflammatory, antioxidative, hepatoprotective, vasorelaxant, antiviral and anticarcinogenic effects. The present review is focused on flavonoids derived from natural products that have shown a wise way to get a true and potentially rich source of drug candidates against liver ailments. The present review initially highlights the current status of flavonoids and their pharmaceutical significance, role of flavonoids in hepatoprotection, therapeutic options available in herbal medicines and in later section, summarizes flavonoids as lead molecules, which have shown significant hepatoprotective activities.

  5. Mechanistic insights into the role of prenyl-binding protein PrBP/δ in membrane dissociation of phosphodiesterase 6

    KAUST Repository

    Qureshi, Bilal M.; Schmidt, Andrea; Behrmann, Elmar; Bü rger, Jö rg; Mielke, Thorsten; Spahn, Christian M. T.; Heck, Martin; Scheerer, Patrick

    2018-01-01

    Isoprenylated proteins are associated with membranes and their inter-compartmental distribution is regulated by solubilization factors, which incorporate lipid moieties in hydrophobic cavities and thereby facilitate free diffusion during trafficking. Here we report the crystal structure of a solubilization factor, the prenyl-binding protein (PrBP/δ), at 1.81 Å resolution in its ligand-free apo-form. Apo-PrBP/δ harbors a preshaped, deep hydrophobic cavity, capacitating apo-PrBP/δ to readily bind its prenylated cargo. To investigate the molecular mechanism of cargo solubilization we analyzed the PrBP/δ-induced membrane dissociation of rod photoreceptor phosphodiesterase (PDE6). The results suggest that PrBP/δ exclusively interacts with the soluble fraction of PDE6. Depletion of soluble species in turn leads to dissociation of membrane-bound PDE6, as both are in equilibrium. This

  6. Mechanistic insights into the role of prenyl-binding protein PrBP/δ in membrane dissociation of phosphodiesterase 6

    KAUST Repository

    Qureshi, Bilal M.

    2018-01-02

    Isoprenylated proteins are associated with membranes and their inter-compartmental distribution is regulated by solubilization factors, which incorporate lipid moieties in hydrophobic cavities and thereby facilitate free diffusion during trafficking. Here we report the crystal structure of a solubilization factor, the prenyl-binding protein (PrBP/δ), at 1.81 Å resolution in its ligand-free apo-form. Apo-PrBP/δ harbors a preshaped, deep hydrophobic cavity, capacitating apo-PrBP/δ to readily bind its prenylated cargo. To investigate the molecular mechanism of cargo solubilization we analyzed the PrBP/δ-induced membrane dissociation of rod photoreceptor phosphodiesterase (PDE6). The results suggest that PrBP/δ exclusively interacts with the soluble fraction of PDE6. Depletion of soluble species in turn leads to dissociation of membrane-bound PDE6, as both are in equilibrium. This

  7. 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.

  8. 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.

  9. Aglaiabbrevins A-D, New Prenylated Bibenzyls from the Leaves of Aglaia abbreviata with Potent PTP1B Inhibitory Activity.

    Science.gov (United States)

    Sun, Pan; Jiang, Chang-Sheng; Zhang, Yi; Liu, Ai-Hong; Liang, Tong-Jun; Li, Jia; Guo, Yue-Wei; Jiang, Jian-Mei; Mao, Shui-Chun; Wang, Bin

    2017-01-01

    Four new prenylated bibenzyls, named aglaiabbrevins A-D (2, 4-6), were isolated from the leaves of Aglaia abbreviata, along with two known related analogues, 3,5-dihydroxy-2-[3,7-dimethyl-2(E),6-octadienyl]bibenzyl (7) and 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl (8). The structures of the new compounds were elucidated on the basis of extensive spectroscopic experiments, mainly one and two dimensional (1D- and 2D)-NMR, and the absolute configuration of 5 was determined by the measurement of specific rotation. The isolated compounds were evaluated for their protein tyrosine phosphatase-1B (PTP1B) inhibitory activity. The results showed that compounds 5-7 exhibited more potent PTP1B inhibitory effects with IC 50 values of 2.58±0.52, 2.44±0.35, and 2.23±0.14 µM, respectively, than the positive control oleanolic acid (IC 50 =2.74±0.20 µM). On the basis of the data obtained, these bibenzyls with the longer C-2 prenyl groups may be considered as potential lead compounds for the development of new anti-obesity and anti-diabetic agents. Also, the PTP1B inhibitory effects for prenylated bibenzyls are being reported for the first time.

  10. 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.

  11. Qualitative and quantitative analysis of flavonoids of the strawberry tree - Arbutus unedo L. (Ericaceae).

    Science.gov (United States)

    Males, Zeljan; Plazibat, Misko; Vundać, Vjera Bilusić; Zuntar, Irena

    2006-06-01

    The leaves and fruits of strawberry tree - Arbutus unedo L., collected from two separate geographic locations in Croatia were investigated to determine their flavonoid composition and content. Quercitrin, isoquercitrin, hyperoside and rutin were identified in all leaf samples by means of thin-layer chromatography; the fruits contained only isoquercitrin. Chlorogenic acid was present in some leaf samples. The content of flavonoids depended on the plant organ investigated, date of collection and the locality. Spectrophotometric determination of the flavonoids indicated that the leaves are richer in flavonoids (0.52-2.00%) than fruits (0.10-0.29%).

  12. Aktivitas antibakteri flavonoid propolis Trigona sp terhadap bakteri Streptococcus mutans (in vitro (In vitro antibacterial activity of flavonoids Trigona sp propolis against Streptococcus mutans

    Directory of Open Access Journals (Sweden)

    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.

  13. Efficient farnesylation of an extended C-terminal C(x)3X sequence motif expands the scope of the prenylated proteome.

    Science.gov (United States)

    Blanden, Melanie J; Suazo, Kiall F; Hildebrandt, Emily R; Hardgrove, Daniel S; Patel, Meet; Saunders, William P; Distefano, Mark D; Schmidt, Walter K; Hougland, James L

    2018-02-23

    Protein prenylation is a post-translational modification that has been most commonly associated with enabling protein trafficking to and interaction with cellular membranes. In this process, an isoprenoid group is attached to a cysteine near the C terminus of a substrate protein by protein farnesyltransferase (FTase) or protein geranylgeranyltransferase type I or II (GGTase-I and GGTase-II). FTase and GGTase-I have long been proposed to specifically recognize a four-amino acid C AAX C-terminal sequence within their substrates. Surprisingly, genetic screening reveals that yeast FTase can modify sequences longer than the canonical C AAX sequence, specifically C( x ) 3 X sequences with four amino acids downstream of the cysteine. Biochemical and cell-based studies using both peptide and protein substrates reveal that mammalian FTase orthologs can also prenylate C( x ) 3 X sequences. As the search to identify physiologically relevant C( x ) 3 X proteins begins, this new prenylation motif nearly doubles the number of proteins within the yeast and human proteomes that can be explored as potential FTase substrates. This work expands our understanding of prenylation's impact within the proteome, establishes the biologically relevant reactivity possible with this new motif, and opens new frontiers in determining the impact of non-canonically prenylated proteins on cell function. © 2018 by The American Society for Biochemistry and Molecular Biology, Inc.

  14. 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,

  15. 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

  16. Flavonoids and terpenoids from Helichrysum forskahlii.

    Science.gov (United States)

    Al-Rehaily, Adnan J; Albishi, Omar A; El-Olemy, Mahmoud M; Mossa, Jaber S

    2008-06-01

    Three new flavonoids, namely helichrysone A (1), helichrysone B (2) and helichrysone C (3) were isolated from the aerial parts of Helichrysum forskahlii, together with 10 known flavonoids, three triterpenes, and one sesquiterpene. The structures of the new flavonoids 1-3 were established by 1D and 2D NMR spectral data. In addition, the antimicrobial activities of the isolated compounds were determined.

  17. Evaluation of Anti-Inflammatory Activity of Prenylated Substances Isolated from Morus alba and Morus nigra

    Czech Academy of Sciences Publication Activity Database

    Zelová, H.; Hanáková, Z.; Čermáková, Z.; Šmejkal, K.; Dall'Acqua, S.; Babula, P.; Cvačka, Josef; Hošek, J.

    2014-01-01

    Roč. 77, č. 6 (2014), s. 1297-1303 ISSN 0163-3864 Grant - others:Operational Programme Education for Competitiveness(XE) CZ.1.07/2.3.00/30.0014 Institutional support: RVO:61388963 Keywords : factor-kappa B * lipopolysaccharide-induced activation * inflammatory gene expression * flavonoids Subject RIV: FR - Pharmacology ; Medidal Chemistry Impact factor: 3.798, year: 2014

  18. The flavonoid pathway in tomato seedlings: transcript abundance and the modeling of metabolite dynamics.

    Directory of Open Access Journals (Sweden)

    Marian Groenenboom

    Full Text Available 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 understood. Here, we study the flavonoid pathway using both experiments and mathematical models. We measured flavonoid metabolite dynamics in two tissues, hypocotyls and cotyledons, during tomato seedling development. Interestingly, the same backbone of interactions leads to very different accumulation patterns in the different tissues. Initially, we developed a mathematical model with constant enzyme concentrations that described the metabolic networks separately in both tissues. This model was unable to fit the measured flavonoid dynamics in the hypocotyls, even if we allowed unrealistic parameter values. This suggested us to investigate the effect of transcript abundance on flavonoid accumulation. We found that the expression of candidate flavonoid genes varies considerably with time. Variation in transcript abundance results in enzymatic variation, which could have a large effect on metabolite accumulation. Candidate transcript abundance was included in the mathematical model as representative for enzyme concentration. We fitted the resulting model to the flavonoid dynamics in the cotyledons, and tested it by applying it to the data from hypocotyls. When transcript abundance is included, we are indeed able to explain flavonoid dynamics in both tissues. Importantly, this is possible under the biologically relevant restriction that the enzymatic properties estimated by the model are conserved between the tissues.

  19. Antioxidant activity of banana flavonoids.

    Science.gov (United States)

    Vijayakumar, S; Presannakumar, G; Vijayalakshmi, N R

    2008-06-01

    The antioxidant activity of flavonoids from banana (Musa paradisiaca) was studied in rats fed normal as well as high fat diets. Concentrations of peroxidation products namely malondialdehyde, hydroperoxides and conjugated diens were significantly decreased whereas the activities of catalase and superoxide dismutase were enhanced significantly. Concentrations of glutathione were also elevated in the treated animals.

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

    Energy Technology Data Exchange (ETDEWEB)

    Mohammed, Intisar Sirour [Faculty of Science, University of Khartoum, Khartoum (Sudan)

    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)

  1. Dynamic changes of flavonoids in Actinidia valvata leaves at different growing stages measured by HPLC-MS/MS.

    Science.gov (United States)

    DU, Qiao-Hui; Zhang, Qiao-Yan; Han, Ting; Jiang, Yi-Ping; Peng, Cheng; Xin, Hai-Liang

    2016-01-01

    Flavonoids are a large group of phenolic secondary metabolites havinga wide range of biochemical and pharmacological effects. Quantitative analysis of flavonoid profiles in the genus Actinidia, which has not been intensively conducted, is useful to a better understanding of the pattern and distribution of flavonoids. In the present work, a liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) method was developed to profile the flavonoids, which was then used to determine the dynamic change of 17 biologically active flavonoids in the leaves of Actinidia valvata at the main growing stages, including glucuronides and acylated di- and triglycosides of flavonoids. The contents of flavonoid triglycosides were significantly higher than other flavonoids. The highest concentrations of kaemperol glycosides were observed in June, while other flavonoids showed highest concentrations in October. On the other hand, the contents of four isorhamnetin glycosides were increased sharply in September to October. The flavonoid profiles seem to be related to temperature, UV-B, and water deficit. Further studies are required to examine the functions of flavonoids in the Actinidia valvata and the underlying molecular mechanisms of actions. Copyright © 2016 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

  2. The regioselectivity of glutathione adduct formation with flavonoid quinone methides is pH-dependent

    NARCIS (Netherlands)

    Awad, H.M.; Boersma, M.G.; Boeren, S.; Vervoort, J.; Bladeren, van P.J.; Rietjens, I.M.C.M.

    2002-01-01

    In the present study, the formation of glutathionyl adducts from a series of 3',4'-dihydroxy flavonoid o-quinone/p-quinone methides was investigated with special emphasis on the regioselectivity of the glutathione addition as a function of pH. The flavonoid o-quinones were generated using

  3. 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.

  4. 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.

  5. Determination of Flavonoids in Wine by High Performance Liquid Chromatography

    Science.gov (United States)

    da Queija, Celeste; Queirós, M. A.; Rodrigues, Ligia M.

    2001-02-01

    The experiment presented is an application of HPLC to the analysis of flavonoids in wines, designed for students of instrumental methods. It is done in two successive 4-hour laboratory sessions. While the hydrolysis of the wines is in progress, the students prepare the calibration curves with standard solutions of flavonoids and calculate the regression lines and correlation coefficients. During the second session they analyze the hydrolyzed wine samples and calculate the concentrations of the flavonoids using the calibration curves obtained earlier. This laboratory work is very attractive to students because they deal with a common daily product whose components are reported to have preventive and therapeutic effects. Furthermore, students can execute preparative work and apply a more elaborate technique that is nowadays an indispensable tool in instrumental analysis.

  6. Prenylated Flavonoids from Morus alba L. Cause Inhibition of G1/S Transition in THP-1 Human Leukemia Cells and Prevent the Lipopolysaccharide-Induced Inflammatory Response

    Czech Academy of Sciences Publication Activity Database

    Kollár, P.; Bárta, T.; Hošek, J.; Souček, Karel; Závalová, V.; Artinian, S.; Talhouk, R.; Smejkal, K.; Suchý, P.; Hampl, A.

    2013-01-01

    Roč. 2013, č. 2013 (2013) ISSN 1741-427X Grant - others:GA MŠk(CZ) ED1.100/02/0123 Institutional support: RVO:68081707 Keywords : ROOT BARK * DIMETHYL-SULFOXIDE * IN-VITRO Subject RIV: BO - Biophysics Impact factor: 2.175, year: 2013

  7. Cloning and molecular analysis of the regulatory factor HiMyb1 in hop (Humulus lupulus L.) and the potential of hop to produce bioactive prenylated flavonoids

    Czech Academy of Sciences Publication Activity Database

    Matoušek, Jaroslav; Vrba, Lukáš; Novák, Petr; Patzak, J.; De Keukeleire, J.; Škopek, Josef; Heyerick, A.; Roldán-Ruiz, I.; De Keukeleire, D.

    2005-01-01

    Roč. 53, - (2005), s. 4793-4798 ISSN 0021-8561 R&D Projects: GA ČR(CZ) GA521/03/0072 Institutional research plan: CEZ:AV0Z50510513 Keywords : molecular analysis * Humulus lupulus L. Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 2.507, year: 2005

  8. Flavonoids as Vasorelaxant Agents: Synthesis, Biological Evaluation and Quantitative Structure Activities Relationship (QSAR Studies

    Directory of Open Access Journals (Sweden)

    Yongzhou Hu

    2011-09-01

    Full Text Available A series of 2-(2-diethylamino-ethoxychalcone and 6-prenyl(or its isomers-flavanones 10a,b and 11a–g were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pretreated with 1 μM phenylephrine (PE. Several compounds showed potent vasorelaxant activities. Compound 10a (EC50 = 7.6 μM, Emax = 93.1%, the most potent one, would be a promising structural template for development of novel and more efficient vasodilators. Further, 2D-QSAR analysis of compounds 10a,b and 11c-e as well as thirty previously synthesized flavonoids 1-3 and 12-38 using Enhanced Replacement Method-Multiple Linear Regression (ERM-MLR was further performed based on an optimal set of molecular descriptors (H5m, SIC2, DISPe, Mor03u and L3m, leading to a reliable model with good predictive ability (Rtrain2 = 0.839, Qloo2 = 0.733 and Rtest2 = 0.804. The results provide good insights into the structure- activity relationships of the target compounds.

  9. Is reversal of endothelial dysfunction by tea related to flavonoid metabolism?

    Science.gov (United States)

    Hodgson, Jonathan M; Puddey, Ian B; Burke, Valerie; Croft, Kevin D

    2006-01-01

    Dietary flavonoids can improve endothelial function, but the response varies between individuals. Wide variability is also seen in flavonoid O-methylation, a major pathway of flavonoid metabolism. The O-methylation of flavonoids could alter activity, and thus influence any effect on endothelial function. The objective of the current analysis was to investigate whether variability in the endothelial function response to ingestion of tea, a rich source of flavonoids, is related to the degree of O-methylation of flavonoids. This relationship was investigated in two studies in which endothelium-dependent flow-mediated dilatation (FMD) of the brachial artery was assessed and urinary 4-O-methylgallic acid (4OMGA) excretion was used as a marker of the O-methylation of tea-derived flavonoids. In the first study, amongst participants consuming five cups of tea per day for 4 weeks, the degree of increase in 4OMGA excretion was inversely associated with the change in FMD responses (r -078, P=0.008). In the second study, there was a significant difference in the FMD responses to acute ingestion of three cups of tea between individuals with a low (median) 4OMGA response (1.94 (sem 0.79) % and -0.25 (sem 0.53) %, respectively; P=0.03). That is, any improvement in FMD following ingestion of tea may be enhanced in individuals who O-methylate less of the absorbed flavonoids. The present results are consistent with the suggestion that differences in flavonoid metabolism may influence their effect on endothelial function. Thus, differences in flavonoid metabolism could be related to the level of benefit of dietary flavonoids on the risk of CVD.

  10. Quantitative determination of sage-leaved rockrose (Cistus salviifolius flavonoids

    Directory of Open Access Journals (Sweden)

    H. M. Elkaib

    2017-01-01

    Full Text Available The widespread use of bioflavonoids, due to their antimicrobial activity and antioxidant properties, necessitates their separate determination in a joint presence. It is noted that the total content of flavonoids, determined by different spectrophotometric methods in the same samples, differs and depends on the structure of the individual flavonoids that make up the samples. The paper presents the results of studies to determine the content of flavonoids in the fraction of the dry extract of shalfeeloid canthus (Cistus salviifolius, which has antimicrobial activity against bacteria of the genus Pseudomonas, which causes damage to protein-containing food products. Curing flavonoids by sequential extraction with aqueous alcohol solutions, filtering and dissolving the dry residue in isopropyl alcohol followed by passing through the gel layers. The following methods for the determination of flavonoids are considered: reaction with Folin-Chikalteu reagent (using quercetin as standard, reaction with aluminum chloride and 2,4-dinitrophenylhydrazine. When oxidized in alkaline medium by the Folin-Chikalteu reagent, which is the phospho-molybdotungstate heteropolycomplexes of flavonols, flavin-3-ol and flavones can be converted into quinoid compounds having absorption bands in the visible region of the spectrum. Only flavones and flavones having hydroxyl groups at positions 3 and 5 can interact with AlCl3. 2,4-dinitrophenylhydrazine only interacts with flavonols. The obtained calibration curves and structural formulas of flavonoids are given, which can be determined by the methods presented. It was found to contain flavonols 0.21 mg / mg, flavones 0.17 mg / mg and flavin-3-ol 0.06 mg/mg.

  11. 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......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......, 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...

  12. 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

  13. 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.

  14. 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.

  15. 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.

  16. Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves.

    Science.gov (United States)

    Orjala, J; Erdelmeier, C A; Wright, A D; Rali, T; Sticher, O

    1993-12-01

    Five new prenylated benzoic acid derivatives, methyl 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxybenzoate (1), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-hydroxybenzoate (2), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (3), methyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (4), and 4-hydroxy-3-(3-methyl-2-butenyl)-5-(3-methyl-2-butenyl)-benzoic acid (5) were isolated from the dried leaves of Piper aduncum L. (Piperaceae). Together with the new metabolites, four known prenylated benzoic acid derivatives, 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoic acid (6), 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoic acid (nervogenic acid, 7), methyl 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoate (8), and methyl 4-hydroxy-3-(3-methyl-2-butenyl)-benzoate (9) as well as, dillapiol (10), myristicin, and the three sesquiterpenes humulene, caryophyllene epoxide, and humulene epoxide were isolated. Compounds 7, 8, and 9 are reported as natural products for the first time. The structures of the isolates were elucidated by spectroscopic methods, mainly 1D-and 2D-NMR spectroscopy. Isolates 4-7, 9, and 10 were molluscicidal while 2, 5-7, and 9 displayed significant antibacterial activities.

  17. Combinatorial Synthesis of Structurally Diverse Triazole-Bridged Flavonoid Dimers and Trimers

    Directory of Open Access Journals (Sweden)

    Tze Han Sum

    2016-09-01

    Full Text Available Flavonoids are a large family of compounds associated with a broad range of biologically useful properties. In recent years, synthetic compounds that contain two flavonoid units linked together have attracted attention in drug discovery and development projects. Numerous flavonoid dimer systems, incorporating a range of monomers attached via different linkers, have been reported to exhibit interesting bioactivities. From a medicinal chemistry perspective, the 1,2,3-triazole ring system has been identified as a particularly attractive linker moiety in dimeric derivatives (owing to several favourable attributes including proven biological relevance and metabolic stability and triazole-bridged flavonoid dimers possessing anticancer and antimalarial activities have recently been reported. However, there are relatively few examples of libraries of triazole-bridged flavonoid dimers and the diversity of flavonoid subunits present within these is typically limited. Thus, this compound type arguably remains underexplored within drug discovery. Herein, we report a modular strategy for the synthesis of novel and biologically interesting triazole-bridged flavonoid heterodimers and also very rare heterotrimers from readily available starting materials. Application of this strategy has enabled step-efficient and systematic access to a library of structurally diverse compounds of this sort, with a variety of monomer units belonging to six different structural subclasses of flavonoid successfully incorporated.

  18. 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.

  19. 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.

  20. 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

  1. 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.

  2. Flavonoids from Lonchocarpus araripensis (Leguminoseae): isolation, unequivocal assignment of NMR signals {sup 1}H and {sup 13}C and conformational analysis; Flavonoides de Lonchocarpus araripensis (Leguminoseae): isolamento, atribuicao inequivoca dos sinais de RMN {sup 1}H e {sup 13}C e analise conformacional

    Energy Technology Data Exchange (ETDEWEB)

    Lima, Almi F.; Ferreira, Daniele A.; Monte, Francisco Jose Q., E-mail: fmonte@dqoi.ufc.br [Universidade Federal do Ceara (UFC), Fortaleza, CE (Brazil). Centro de Ciencias. Departamento de Quimica Organica e Inorganica; Braz-Filho, Raimundo [Universidade Estadual do Norte Fluminense (UENF), Campo dos Goytacazes, RJ (Brazil). Centro de Ciencias Tecnologicas. Laboratorio de Ciencias Quimicas

    2014-07-01

    In a continuing investigation for potentially bioactive natural products, flavonoids were isolated from Lonchocarpus araripensis (Leguminoseae) and identified as 3-methoxy-6-O-prenyl-6'',6''-dimethylchromene-[7,8,2'',3'']-flavone (1), 3,6-dimethoxy-6'',6''-dimethylchromene-[7,8,2'',3'']-flavone (2) and 3,5,8-trimethoxy-[6,7,2{sup ,}3{sup ]}-furanoflavone (3). This is the first time compound 3 has been described. Compound 2 has been previously isolated from roots while this is the first time 1 is reported in this species. Complete NMR assignments are given for 1 ,2 and 3 together with the determination of conformation for 1. (author)

  3. Mechanistic insights into Mg2+-independent prenylation by CloQ from classical molecular mechanics and hybrid quantum mechanics/molecular mechanics molecular dynamics simulations.

    Science.gov (United States)

    Bayse, Craig A; Merz, Kenneth M

    2014-08-05

    Understanding the mechanism of prenyltransferases is important to the design of engineered proteins capable of synthesizing derivatives of naturally occurring therapeutic agents. CloQ is a Mg(2+)-independent aromatic prenyltransferase (APTase) that transfers a dimethylallyl group to 4-hydroxyphenylpyruvate in the biosynthetic pathway for clorobiocin. APTases consist of a common ABBA fold that defines a β-barrel containing the reaction cavity. Positively charged basic residues line the inside of the β-barrel of CloQ to activate the pyrophosphate leaving group to replace the function of the Mg(2+) cofactor in other APTases. Classical molecular dynamics simulations of CloQ, its E281G and F68S mutants, and the related NovQ were used to explore the binding of the 4-hydroxyphenylpyruvate (4HPP) and dimethylallyl diphosphate substrates in the reactive cavity and the role of various conserved residues. Hybrid quantum mechanics/molecular mechanics potential of mean force (PMF) calculations show that the effect of the replacement of the Mg(2+) cofactor with basic residues yields a similar activation barrier for prenylation to Mg(2+)-dependent APTases like NphB. The topology of the binding pocket for 4HPP is important for selective prenylation at the ortho position of the ring. Methylation at this position alters the conformation of the substrate for O-prenylation at the phenol group. Further, a two-dimensional PMF scan shows that a "reverse" prenylation product may be a possible target for protein engineering.

  4. 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

  5. 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

  6. Antiherpetic activity of a flavonoid fraction from Ocotea notata leaves

    Directory of Open Access Journals (Sweden)

    Rafael Garrett

    2012-01-01

    Full Text Available This study describes the isolation of a flavonoid fraction from leaves of Ocotea notata (Nees & Mart. Mez, Lauraceae, the identification of six major compounds (an A-type proanthocyanidin trimer [3], isoquercitrin [4], reynoutrin [5], miquelianin [6], quercitrin [7], afzelin [8] and four minor compounds (catechin [1], epicatechin [2], quercetin [9], kaempferol [10] present in the fraction and its activity against the Herpes simplex virus type 1 (HSV-1 and type 2 (HSV-2. The 50% effective concentrations values (EC50 calculated from the dose-response curve and the selectivity indices (SI against the virus were: EC50 35.8 µg/mL and SI 5.5 to HSV-1 and EC50 23.5 µg/mL and SI 8.5 to HSV-2. The flavonoid fraction was more active against HSV-2 than HSV-1. The mechanisms of antiviral action of the flavonoid fraction against the virus were also evaluated. The percentage inhibition (PI obtained for HSV-2 was higher than 90% in the following assays: virucidal, pre-treatment of cells, treatment of cells after viral adsorption and treatment of cells after viral penetration. For HSV-1, the flavonoid fraction had no effect in pre-treatment of cells and showed 60% of inhibition in virucidal assay.

  7. Antiherpetic activity of a flavonoid fraction from Ocotea notata leaves

    Directory of Open Access Journals (Sweden)

    Rafael Garrett

    2012-04-01

    Full Text Available This study describes the isolation of a flavonoid fraction from leaves of Ocotea notata (Nees & Mart. Mez, Lauraceae, the identification of six major compounds (an A-type proanthocyanidin trimer [3], isoquercitrin [4], reynoutrin [5], miquelianin [6], quercitrin [7], afzelin [8] and four minor compounds (catechin [1], epicatechin [2], quercetin [9], kaempferol [10] present in the fraction and its activity against the Herpes simplex virus type 1 (HSV-1 and type 2 (HSV-2. The 50% effective concentrations values (EC50 calculated from the dose-response curve and the selectivity indices (SI against the virus were: EC50 35.8 µg/mL and SI 5.5 to HSV-1 and EC50 23.5 µg/mL and SI 8.5 to HSV-2. The flavonoid fraction was more active against HSV-2 than HSV-1. The mechanisms of antiviral action of the flavonoid fraction against the virus were also evaluated. The percentage inhibition (PI obtained for HSV-2 was higher than 90% in the following assays: virucidal, pre-treatment of cells, treatment of cells after viral adsorption and treatment of cells after viral penetration. For HSV-1, the flavonoid fraction had no effect in pre-treatment of cells and showed 60% of inhibition in virucidal assay.

  8. 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.

  9. 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,

  10. Antimicrobial action of purified raspberry flavonoid

    African Journals Online (AJOL)

    user

    2012-02-07

    Feb 7, 2012 ... numerous research groups have sought to elucidate the antibacterial mechanisms of action of selected flavonoids. *Corresponding author. E-mail: bdsunjinxu@163.com. (Cushnie et al., 2005), but there have been no reports on the bacteriostatic and bactericidal action of raspberry flavonoid. In this paper ...

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

    African Journals Online (AJOL)

    ajl yemi

    2011-12-19

    Dec 19, 2011 ... Key words: Astragalus squarrosus, antioxidant, phenolics, flavonoids. INTRODUCTION ... Phenolic and flavonoid compounds are widely distri- buted plant constituents. ..... Antioxidant effects of some ginger constituents.

  12. Flavonoids as fruit and vegetable intake biomarkers

    DEFF Research Database (Denmark)

    Krogholm, Kirstine Suszkiewicz

    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...... weaker than in 24h urine samples, indicating that the 24h urinary recovery of the 7 flavonoids is a stronger biomarker of the intake of fruit and vegetables than the urinary recovery of the 7 flavonoids in morning spot urine. In Paper II, the biokinetic profiles of some of the most important dietary......-individual variation in the absorption and urinary recovery of the flavonoids, and this makes it very difficult to separate individuals according to intake by use of the flavonoid biomarker in urine. The intra-individual variation was on the contrary low, and Paper II therefore supports the assumption, that 24h...

  13. Prenylated flavone from roots of a hybrid between Artocarpus heterophyllus and Artocarpus integer and its biological activities

    International Nuclear Information System (INIS)

    Panthong, Kanda; Tohdee, Kanogwan; Hutadilok-Towatana, Nongporn; Voravuthikunchai, Supayang P.; Chusri, Sasitorn

    2013-01-01

    One new prenylated flavone, 2,8-dihydroxy-3,10-dimethoxy-6-(2-methyl-1-propen-1-yl)- 6H,7H-[1]benzopyrano[4,3-b][1]-benzopyran-7-one, together with 24 known compounds were isolated from crude acetone extract from the roots of a hybrid between Artocarpus heterophyllus and Artocarpus integer. Their structures were determined by 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data. The antioxidant and antibacterial activities of the isolated compounds were evaluated. The new compound showed potent antioxidant activity against DPPH• and superoxide with IC 50 values of 0.033 and 0.125 mg mL -1 , respectively. Significant antibacterial activity against Acinetobacter baumannii was observed with MIC value of 50 μg mL -1 . (author)

  14. Loss of HMG-CoA reductase in C. elegans causes defects in protein prenylation and muscle mitochondria.

    Directory of Open Access Journals (Sweden)

    Parmida Ranji

    Full Text Available HMG-CoA reductase is the rate-limiting enzyme in the mevalonate pathway and the target of cholesterol-lowering statins. We characterized the C. elegans hmgr-1(tm4368 mutant, which lacks HMG-CoA reductase, and show that its phenotypes recapitulate that of statin treatment, though in a more severe form. Specifically, the hmgr-1(tm4368 mutant has defects in growth, reproduction and protein prenylation, is rescued by exogenous mevalonate, exhibits constitutive activation of the UPRer and requires less mevalonate to be healthy when the UPRmt is activated by a constitutively active form of ATFS-1. We also show that different amounts of mevalonate are required for different physiological processes, with reproduction requiring the highest levels. Finally, we provide evidence that the mevalonate pathway is required for the activation of the UPRmt.

  15. Prenylated flavone from roots of a hybrid between Artocarpus heterophyllus and Artocarpus integer and its biological activities

    Energy Technology Data Exchange (ETDEWEB)

    Panthong, Kanda [Prince of Songkla University (Thailand). Natural Product Research Center of Excellence; Tohdee, Kanogwan [Prince of Songkla University (Thailand). Faculty of Science. Department of Chemistry; Hutadilok-Towatana, Nongporn [Prince of Songkla University (Thailand). Dept. of Biochemistry; Voravuthikunchai, Supayang P. [Prince of Songkla University (Thailand). Faculty of Science. Department of Microbiology; Chusri, Sasitorn [Prince of Songkla University (Thailand). Faculty of Traditional Thai Medicine

    2013-10-15

    One new prenylated flavone, 2,8-dihydroxy-3,10-dimethoxy-6-(2-methyl-1-propen-1-yl)- 6H,7H-[1]benzopyrano[4,3-b][1]-benzopyran-7-one, together with 24 known compounds were isolated from crude acetone extract from the roots of a hybrid between Artocarpus heterophyllus and Artocarpus integer. Their structures were determined by 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data. The antioxidant and antibacterial activities of the isolated compounds were evaluated. The new compound showed potent antioxidant activity against DPPH Bullet and superoxide with IC{sub 50} values of 0.033 and 0.125 mg mL{sup -1}, respectively. Significant antibacterial activity against Acinetobacter baumannii was observed with MIC value of 50 {mu}g mL{sup -1}. (author)

  16. Two novel prenylated kaempferol derivatives from fresh bud's fur of Platanus acerifolia and their anti-proliferative activities.

    Science.gov (United States)

    Zuo, Bo; Liao, Zhi-Xin; Xu, Chen; Liu, Chao

    2016-01-06

    Two novel prenylated kaempferol derivatives (1, 2), together with seven known metabolites were isolated from ethanol extract of fresh Platanus acerifolia bud's fur by multistep chromatographic processing. Structure of compounds 1 and 2 was confirmed by 1D, 2D NMR spectra and HR-ESI-MS. In addition, compound 1 was further analysed by X-ray crystallography. Anti-proliferative activities in vitro against human breast carcinoma (MCF-7) and human hepatocellular carcinoma (Hep-G2) cell lines for compound 1, 2 and 8 were evaluated. Compound 1 exhibited cytotoxic activity towards MCF-7 and Hep-G2 cell lines with the IC 50 values 38.2 and 39.5 μM, respectively. Moreover, compound 2 showed weak cytotoxic activities against the two cell lines.

  17. Competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors, prenylated caged xanthones from Garcinia hanburyi and their inhibitory mechanism.

    Science.gov (United States)

    Tan, Xue Fei; Uddin, Zia; Park, Chanin; Song, Yeong Hun; Son, Minky; Lee, Keun Woo; Park, Ki Hun

    2017-04-15

    Protein tyrosine phosphatase 1B (PTP1B) plays important role in diabetes, obesity and cancer. The methanol extract of the gum resin of Garcinia hanburyi (G. hanburyi) showed potent PTP1B inhibition at 10µg/ml. The active compounds were identified as prenylated caged xanthones (1-9) which inhibited PTP1B in dose-dependent manner. Carboxybutenyl group within caged motif (A ring) was found to play a critical role in enzyme inhibition such as 1-6 (IC 50 s=0.47-4.69µM), whereas compounds having hydroxymethylbutenyl 7 (IC 50 =70.25µM) and methylbutenyl 8 (IC 50 >200µM) showed less activity. The most potent inhibitor, gambogic acid 1 (IC 50 =0.47µM) showed 30-fold more potency than ursolic acid (IC 50 =15.5µM), a positive control. In kinetic study, all isolated xanthones behaved as competitive inhibitors which were fully demonstrated with K m , V max and K ik /K iv ratio. It was also proved that inhibitor 1 operated under the enzyme isomerization model having k 5 =0.0751µM - 1 S - 1 , k 6 =0.0249µM - 1 S - 1 and K i app =0.499µM. To develop a pharmacophore model, we explored the binding sites of compound 1 and 7 in PTP1B. These modeling results were in agreement with our findings, which revealed that the inhibitory activities are tightly related to caged motif and prenyl group in A ring. Copyright © 2017 Elsevier Ltd. All rights reserved.

  18. 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.

  19. Effect of flavonoids on human health: old subjects but new challenges.

    Science.gov (United States)

    Lee, Eung-Ryoung; Kang, Geun-Ho; Cho, Ssang-Goo

    2007-01-01

    Flavonoids are highly diversified plant pigments that are present in a wide range of fruits, vegetables, nuts, and beverages. They are regularly consumed in the human diet and have various biological activities including anti-inflammatory, anti-cancer, and anti-viral properties. The flavonoids maybe one of the safest non-immunogenic drugs because they are small organic compounds which have been normally absorbed by the human body for long time. During the past decades, the patents on their health effects have inflated very much and the yearly number of the patents is on an increasing trend. This review summarizes the current patents on the health effects of various flavonoids, and suggests the possible expectation that a wide variety of diseases are successful treated with newly-developed specific flavonoids or their derivatives in the near future. In recent patents, specific flavonoids were described to function as anti-oxidants, enzyme inhibitors, hormones, or immune modulators. Moreover, the recent patents also tried to provide the molecular mechanism of the flavonoid compounds on treating or preventing various human diseases. Recent mechanistic studies in molecular level make it possible that specific flavonoids are identified to have a wide range of biological properties that can contribute to the beneficial effects on human health.

  20. Catalase inhibition an anti cancer property of flavonoids: A kinetic and structural evaluation.

    Science.gov (United States)

    Majumder, Debashis; Das, Asmita; Saha, Chabita

    2017-11-01

    Flavonoids are dietary polyphenols that present abundantly in fruits and vegetables. Flavonoids have inhibitory effects on enzymes and catalase is one among them. Catalase is a common enzyme ubiquitously found in all living organisms exposed to oxygen. It catalyzes the decomposition of hydrogen peroxide to water and oxygen (2H 2 O 2 →2H 2 O+O 2 ) . Inhibition of pure and cellular catalase from K562 cells by flavonoids was similar and exhibited the following efficacy; Myrecetin>Quercetin>Kaempferol and Quercetin>Luteolin>Apigenin demonstrating structure activity relationship. Circular Dichroism (CD) spectra have shown distinct loss in α-helical structure of the catalase on interaction with the flavonoids. All flavonoids inhibited the catalase activity by uncompetitive mechanism. The K m and V max values of pure catalase were observed to be 294mM -1 and 0.222mM -1 s -1 respectively and on inhibition with myrecetin the values decreased to a minimum of 23mM -1 and 0.014mM -1 s -1 respectively. Inhibition of catalase will directly results in increased production of Reactive Oxygen Species (ROS) and pro-oxidant property of flavonoids. This inhibition was reversed in presence of Cu 2+ ions because of the chelating affect of flavonoids. Copyright © 2017 Elsevier B.V. All rights reserved.

  1. Eriosema (Fabaceae) Species Represent a Rich Source of Flavonoids with Interesting Pharmacological Activities.

    Science.gov (United States)

    Awouafack, Maurice Ducret; Tane, Pierre; Spiteller, Michael; Eloff, Jacobus Nicolaas

    2015-07-01

    Many flavonoids have so far been isolated as main secondary metabolites in plant species of the genus Eriosema (Fabaceae), which contains approximately 160 species. A total of 52 flavonoids including isoflavones, dihydroflavonols, flavonols, flavanones, dihydrochalcones, isoflavanone and their pyrano or glucoside derivatives were isolated and characterized from the five species of this genus investigated to date. Total synthesis and semi-synthesis (acetylation, methylation, hydrogenation, and cyclization) of some isolated flavonoids were reported. Due to several significant pharmacological properties (antimicrobial, cytotoxicity, anti-mycobacterial, antioxidant, antiviral, erectile-dysfunction, vasodilatory and hypoglycemic) of the isolated flavonoids and derivatives, more scientists should be interested in investigating Eriosema species. The present review is the first to document all flavonoids that have been reported from the genus Eriosema to date together with their synthetic and semi-synthetic derivatives, and their pharmacological properties. Dihydrochalcones, which are precursors of other classes of flavonoids, are very rare in natural sources and their isolation from Eriosema species may explain the large number of flavonoids found in this genus. It appears that isoflavone could be a marker for species in this genus. The 83 flavonoids (1-83) documented include 52 isolates, 31 semi-synthetic and 3 totally synthetic derivatives. Data were obtained from Google scholar, Pubmed, Scifinder, Sciencedirect, and Scopus. With 52 different flavonoids isolated from only 5 of the approximately 160 species it shows the remarkable chemical diversity of this genus. This compilation of the biological activities and chemical composition may renew the interest of pharmacologists and phytochemists in this genus.

  2. A chemical profiling strategy for semi-quantitative analysis of flavonoids in Ginkgo extracts.

    Science.gov (United States)

    Yang, Jing; Wang, An-Qi; Li, Xue-Jing; Fan, Xue; Yin, Shan-Shan; Lan, Ke

    2016-05-10

    Flavonoids analysis in herbal products is challenged by their vast chemical diversity. This work aimed to develop a chemical profiling strategy for the semi-quantification of flavonoids using extracts of Ginkgo biloba L. (EGB) as an example. The strategy was based on the principle that flavonoids in EGB have an almost equivalent molecular absorption coefficient at a fixed wavelength. As a result, the molecular-contents of flavonoids were able to be semi-quantitatively determined by the molecular-concentration calibration curves of common standards and recalculated as the mass-contents with the characterized molecular weight (MW). Twenty batches of EGB were subjected to HPLC-UV/DAD/MS fingerprinting analysis to test the feasibility and reliability of this strategy. The flavonoid peaks were distinguished from the other peaks with principle component analysis and Pearson correlation analysis of the normalized UV spectrometric dataset. Each flavonoid peak was subsequently tentatively identified by the MS data to ascertain their MW. It was highlighted that the flavonoids absorption at Band-II (240-280 nm) was more suitable for the semi-quantification purpose because of the less variation compared to that at Band-I (300-380 nm). The semi-quantification was therefore conducted at 254 nm. Beyond the qualitative comparison results acquired by common chemical profiling techniques, the semi-quantitative approach presented the detailed compositional information of flavonoids in EGB and demonstrated how the adulteration of one batch was achieved. The developed strategy was believed to be useful for the advanced analysis of herbal extracts with a high flavonoid content without laborious identification and isolation of individual components. Copyright © 2016 Elsevier B.V. All rights reserved.

  3. Flavonoids in Kidney Health and Disease

    Directory of Open Access Journals (Sweden)

    Félix Vargas

    2018-04-01

    Full Text Available This review summarizes the latest advances in knowledge on the effects of flavonoids on renal function in health and disease. Flavonoids have antihypertensive, antidiabetic, and antiinflammatory effects, among other therapeutic activities. Many of them also exert renoprotective actions that may be of interest in diseases such as glomerulonephritis, diabetic nephropathy, and chemically-induced kidney insufficiency. They affect several renal factors that promote diuresis and natriuresis, which may contribute to their well-known antihypertensive effect. Flavonoids prevent or attenuate the renal injury associated with arterial hypertension, both by decreasing blood pressure and by acting directly on the renal parenchyma. These outcomes derive from their interference with multiple signaling pathways known to produce renal injury and are independent of their blood pressure-lowering effects. Oral administration of flavonoids prevents or ameliorates adverse effects on the kidney of elevated fructose consumption, high fat diet, and types I and 2 diabetes. These compounds attenuate the hyperglycemia-disrupted renal endothelial barrier function, urinary microalbumin excretion, and glomerular hyperfiltration that results from a reduction of podocyte injury, a determinant factor for albuminuria in diabetic nephropathy. Several flavonoids have shown renal protective effects against many nephrotoxic agents that frequently cause acute kidney injury (AKI or chronic kidney disease (CKD, such as LPS, gentamycin, alcohol, nicotine, lead or cadmium. Flavonoids also improve cisplatin- or methotrexate-induced renal damage, demonstrating important actions in chemotherapy, anticancer and renoprotective effects. A beneficial prophylactic effect of flavonoids has been also observed against AKI induced by surgical procedures such as ischemia/reperfusion (I/R or cardiopulmonary bypass. In several murine models of CKD, impaired kidney function was significantly improved by

  4. Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2

    NARCIS (Netherlands)

    Zanden, J.J. van; Wortelboer, H.M.; Bijlsma, S.; Punt, A.; Usta, M.; Bladeren, P.J.V.; Rietjens, I.M.C.M.; Cnubben, N.H.P.

    2005-01-01

    In the present study, the effects of a large series of flavonoids on multidrug resistance proteins (MRPs) were studied in MRP1 and MRP2 transfected MDCKII cells. The results were used to define the structural requirements of flavonoids necessary for potent inhibition of MRP1- and MRP2-mediated

  5. Exploring the molecular targets of dietary flavonoid fisetin in cancer

    OpenAIRE

    Syed, Deeba N.; Adhami, Vaqar Mustafa; Khan, Naghma; Khan, Mohammad Imran; Mukhtar, Hasan

    2016-01-01

    The last few decades have seen a resurgence of interest among the scientific community in exploring the efficacy of natural compounds against various human cancers. Compounds of plant origin belonging to different groups such as alkaloids, flavonoids and polyphenols evaluated for their cancer preventive effects have yielded promising data, thereby offering a potential therapeutic alternative against this deadly disease. The flavonol fisetin (3,3′,4′,7-tetrahydroxyflavone), present in fruits a...

  6. Flavonoid 4′-O-Methylkuwanon E from Morus alba Induces the Differentiation of THP-1 Human Leukemia Cells

    Directory of Open Access Journals (Sweden)

    Peter Kollar

    2015-01-01

    Full Text Available Aims. In this work we studied cytodifferentiation effects of newly characterized prenyl flavonoid 4′-O-methylkuwanon E (4ME isolated from white mulberry (Morus alba L.. Main Methods. Cell growth and viability were measured by dye exclusion assay; cell cycle and surface antigen CD11b were monitored by flow cytometry. For the cytodifferentiation of cells the NBT reduction assay was employed. Regulatory proteins were assessed by western blotting. Key Findings. 4ME induced dose-dependent growth inhibition of THP-1 cells, which was not accompanied by toxic effect. Inhibition of cells proliferation caused by 4ME was associated with the accumulation in G1 phase and with downregulation of hyperphosphorylated pRb. Treatment with 4ME led to significant induction of NBT-reducing activity of PMA stimulated THP-1 cells and upregulation expression of differentiation-associated surface antigen CD11b. Our results suggest that monocytic differentiation induced by 4ME is connected with up-regulation of p38 kinase activity. Significance. Our study provides the first evidence that 4ME induces the differentiation of THP-1 human monocytic leukemia cells and thus is a potential cytodifferentiating anticancer agent.

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

    African Journals Online (AJOL)

    SARAH

    2014-12-29

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

  8. 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...

  9. 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...

  10. 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 (

  11. 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

  12. Gamma radiation induced enhancement in the antioxidant and radioprotective activities of flavonoids

    International Nuclear Information System (INIS)

    Arul Anantha Kumar, A.; Sonwani, Swetha; Bakkiam, D.

    2018-01-01

    Recently γ-radiation has been used as a tool to induce structural changes in natural biomolecules to enhance their biological and physiological properties. Flavonoids are a family of plant derived polyphenolic compounds having considerable scientific and therapeutic importance. Structurally they are the benzo-γ-pyrone derivatives containing phenolic and pyrane rings. Flavonoid radioprotection is an intense area of research thanks to features like natural origin, effectiveness at non-toxic dose levels and lack of side effects. But till date no report is available on the effect of γ-radiation mediated enhancement in radioprotection activity of flavonoids. In view of this the present study was carried out to determine the γ-radiation induced structural changes in selected flavonoids i.e. apigenin, naringenin and genistein and also to explore the possibility of enhancement in their antioxidant and radioprotective activities

  13. 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.

  14. Foliar flavonoids of nine species of Bauhinia

    OpenAIRE

    SALATINO, ANTONIO; BLATT, CECÍLIA T.T.; SANTOS, DÉBORAH Y.A.C. DOS; VAZ, ANGELA M.S.F.

    1999-01-01

    Foliar flavonoids of nine species of Bauhinia were isolated and identified. All the compounds correspond to glycosides derived from kaempferol, quercetin, isorhamnetin and myricetin. Derivatives of the latter aglyconhe seem to be rare in Bauhinia. Derivatives of isorhamnetin are commonly found in species of subgenus Bauhinia and were not detected in the two species of subgenus Phanera. Flavonoid patterns of species of the former subgenus are in general more complex than those of the latter. ...

  15. 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.

  16. Functions of flavonoids in the central nervous system: Astrocytes as targets for natural compounds.

    Science.gov (United States)

    Matias, Isadora; Buosi, Andrea Schmidt; Gomes, Flávia Carvalho Alcantara

    2016-05-01

    In the last decade, there have been major advances in the understanding of the role of glial cells as key elements in the formation, maintenance and refinement of synapses. Recently, the discovery of natural compounds capable of modulating nervous system function has revealed new perspectives on the restoration of the injured brain. Among these compounds, flavonoids stand out as molecules easily obtainable in the diet that have remarkable effects on cognitive performance and behavior. Nevertheless, little is known about the cellular and molecular mechanisms underlying the actions of flavonoids in the nervous system. The present review presents recent advances in the effects of natural compounds, particularly flavonoids, in the nervous system. We shed light on astrocytes as targets of flavonoids and discuss how this interaction might contribute to the effects of flavonoids on neuronal survival, differentiation and function. Finally, we discuss how the effects of flavonoids on astrocytes might contribute to the development of alternative therapeutic approaches to the treatment of neural diseases. Copyright © 2016 Elsevier Ltd. All rights reserved.

  17. Quantitative determination of total and individual flavonoids in stems and leaves of Buddleja davidii and Buddleja albiflora.

    Science.gov (United States)

    Ying, Cheng; Wan, Dingrong

    2012-10-01

    Buddleja davidii and B. albiflora are two different original plants of the famous crude medicine "Diaoyangchen". An ultraviolet-visible spectrophotometric method and a HPLC method were used for the determination of total and individual flavonoids (luteolin and apigenin) contents from their stems and leaves for the first time. From the comparative evaluation, remarkable differences in flavonoids contents were observed between different origins and different parts of the samples. And content of specific flavonoid did not correspond to the total flavonoids contents in Buddleja davidii and Buddleja albiflora. With a better accuracy and precision, the methods had been proved simple, rapid, and reliable for quantitative determination of the total flavonoids and luteolin and apigenin in the two phytomedicines. Furthermore, our present study will pave the way of guidelines for the differentiation and standardization and exploitation of individual parts of this herb material.

  18. The Prenylated Rab GTPase Receptor PRA1.F4 Contributes to Protein Exit from the Golgi Apparatus.

    Science.gov (United States)

    Lee, Myoung Hui; Yoo, Yun-Joo; Kim, Dae Heon; Hanh, Nguyen Hong; Kwon, Yun; Hwang, Inhwan

    2017-07-01

    Prenylated Rab acceptor1 (PRA1) functions in the recruitment of prenylated Rab proteins to their cognate organelles. Arabidopsis ( Arabidopsis thaliana ) contains a large number of proteins belonging to the AtPRA1 family. However, their physiological roles remain largely unknown. Here, we investigated the physiological role of AtPRA1.F4, a member of the AtPRA1 family. A T-DNA insertion knockdown mutant of AtPRA1.F4 , atpra1.f4 , was smaller in stature than parent plants and possessed shorter roots, whereas transgenic plants overexpressing HA:AtPRA1.F4 showed enhanced development of secondary roots and root hairs. However, both overexpression and knockdown plants exhibited increased sensitivity to high-salt stress, lower vacuolar Na + /K + -ATPase and plasma membrane ATPase activities, lower and higher pH in the vacuole and apoplast, respectively, and highly vesiculated Golgi apparatus. HA:AtPRA1.F4 localized to the Golgi apparatus and assembled into high-molecular-weight complexes. atpra1.f4 plants displayed a defect in vacuolar trafficking, which was complemented by low but not high levels of HA : AtPRA1.F4 Overexpression of HA:AtPRA1.F4 also inhibited protein trafficking at the Golgi apparatus, albeit differentially depending on the final destination or type of protein: trafficking of vacuolar proteins, plasma membrane proteins, and trans-Golgi network (TGN)-localized SYP61 was strongly inhibited; trafficking of TGN-localized SYP51 was slightly inhibited; and trafficking of secretory proteins and TGN-localized SYP41 was negligibly or not significantly inhibited. Based on these results, we propose that Golgi-localized AtPRA1.F4 is involved in the exit of many but not all types of post-Golgi proteins from the Golgi apparatus. Additionally, an appropriate level of AtPRA1.F4 is crucial for its function at the Golgi apparatus. © 2017 American Society of Plant Biologists. All Rights Reserved.

  19. 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.

  20. [Advance in flavonoids biosynthetic pathway and synthetic biology].

    Science.gov (United States)

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

    2016-11-01

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

  1. Correlation of binding efficacies of DNA to flavonoids and their induced cellular damage.

    Science.gov (United States)

    Das, Asmita; Majumder, Debashis; Saha, Chabita

    2017-05-01

    Flavonoids are dietary intakes which are bestowed with several health benefits. The most studied property of flavonoids is their antioxidant efficacy. Among the chosen flavonoids Quercetin, Kaempferol and Myricetin is catagorized as flavonols whereas Apigenin and Luteolin belong to the flavone group. In the present study anti-cancer properties of flavonoids are investigated on the basis of their binding efficacy to ct-DNA and their ability to induce cytotoxicity in K562 leukaemic cells. The binding affinities of the flavonoids with calf thymus DNA (ct-DNA) are in the order Quercetin>Myricetin>Luteolin>Kaempferol>Apigenin. Quercetin with fewer OH than myricetin has higher affinity towards DNA suggesting that the number and position of OH influence the binding efficacies of flavonoids to ct-DNA. CD spectra and EtBr displacement studies evidence myricetin and apigenin to be stronger intercalators of DNA compared to quercetin. From comet assay results it is observed that quercetin and myricetin when used in combination induce higher DNA damage in K562 leukemic cells than when tested individually. Higher binding efficacy has been recorded for quercetin to DNA at lower pH, which is the micro environment of cancerous cells, and hence quercetin can act as a potential anti-cancer agent. Presence of Cu also increases cellular damage as recorded by comet assay. Copyright © 2017. Published by Elsevier B.V.

  2. Deciphering the binding behavior of flavonoids to the cyclin dependent kinase 6/cyclin D complex.

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    Jingxiao Zhang

    Full Text Available Flavonoids, a class of natural compounds with variable phenolic structures, have been found to possess anti-cancer activities by modulating different enzymes and receptors like CDK6. To understand the binding behavior of flavonoids that inhibit the active CDK6, molecular dynamics (MD simulations were performed on six inhibitors, chrysin (M01, fisetin (M03, galangin (M04, genistein (M05, quercetin (M06 and kaempferol (M07, complexed with CDK6/cyclin D. For all six flavonoids, the 3'-OH and 4'-OH of B-ring were found to be favorable for hydrogen bond formation, but the 3-OH on the C-ring and 5-OH on the A-ring were unfavorable, which were confirmed by the MD simulation results of the test molecule, 3', 4', 7-trihydroxyflavone (M15. The binding efficiencies of flavonoids against the CDK6/cyclin D complex were mainly through the electrostatic (especially the H-bond force and vdW interactions with residues ILE19, VAL27, ALA41, GLU61, PHE98, GLN103, ASP163 and LEU152. The order of binding affinities of these flavonoids toward the CDK6/cyclin D was M03 > M01 > M07 > M15 > M06 > M05 > M04. It is anticipated that the binding features of flavonoid inhibitors studied in the present work may provide valuable insights for the development of CDK6 inhibitors.

  3. Phytochemical screening and quantification of flavonoids from leaf extract of Jatropha curcas Linn.

    Science.gov (United States)

    Ebuehi, O A T; Okorie, N A

    2009-01-01

    The Jatropha curcas L. (Euphorbiaceae) herb is found in SouthWest, Nigeria and other parts of West Africa, and is claimed to possess anti-hypertensive property. The phytochemical screening and flavonoid quantification of the leaf extract of Jatropha curcas Linn were studied. The phytochemical screening of the methanolic leaf extract of J. curcas L. was carried using acceptable and standard methods. The flavonoid contents of the leaf extract of Jatropha curcas L. were determined using thin layer chromatography (TLC), infrared spectroscopy (IRS) and a reversed phase high performance liquid chromatography (HPLC). The phytochemical screening of the methanolic extract of the leaves of the plant shows the presence of alkaloids, cardiac glycosides, cyanogenic glycosides, phlobatannins, tannins, flavonoids and saponins. To quantify the flavonoid contents of leaf extract of Jatropha curcas L, extracts from the plant samples where examined in a C-18 column with UV detection and isocratic elution with acetonitrile; water (45:55). Levels of flavonoids (flavones) in leaves ranged from 6:90 to 8:85 mg/g dry weight. Results indicate that the methanolic extract of the leaves of Jatropha curcas L. contains useful active ingredients which may serve as potential drug for the treatment of diseases. In addition, a combination of TLC, IRS and HPLC can be used to analyse and quantify the flavonoids present in the leaves of Jatropha curcas L.

  4. 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

  5. Identification of a flavonoid C-glycoside as potent antioxidant.

    Science.gov (United States)

    Wen, Lingrong; Zhao, Yupeng; Jiang, Yueming; Yu, Limei; Zeng, Xiaofang; Yang, Jiali; Tian, Miaomiao; Liu, Huiling; Yang, Bao

    2017-09-01

    Flavonoids have been documented to have good antioxidant activities in vitro. However, reports on the cellular antioxidant activities of flavonoid C-glycosides are very limited. In this work, an apigenin C-glycoside was purified from Artocarpus heterophyllus by column chromatography and was identified to be 2″-O-β-D-xylosylvitexin by nuclear magnetic resonance spectroscopy. The cellular antioxidant activity and anticancer activity of 2″-O-β-D-xylosylvitexin were evaluated for the first time. The quantitative structure-activity relationship was analysed by molecular modeling. Apigenin presented an unexpected cellular antioxidation behaviour. It had an antioxidant activity at low concentration and a prooxidant activity at high concentration, whereas 2″-O-β-D-xylosylvitexin showed a dose-dependent cellular antioxidant activity. It indicated that C-glycosidation improved the cellular antioxidation performance of apigenin and eliminated the prooxidant effect. The ortho-dihydroxyl at C-3'/C-4' and C-3 hydroxyl in the flavonoid skeleton play important roles in the antioxidation behaviour. The cell proliferation assay revealed a low cytotoxicity of 2″-O-β-D-xylosylvitexin. Copyright © 2017 Elsevier Inc. All rights reserved.

  6. 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.

  7. 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.

  8. Comparison of different extraction methods and HPLC quantification of prenylated and unprenylated phenylpropanoids in raw Italian propolis.

    Science.gov (United States)

    Taddeo, Vito Alessandro; Epifano, Francesco; Fiorito, Serena; Genovese, Salvatore

    2016-09-10

    In this paper the presence of selected prenylated and unprenylated phenylpropanoids, namely ferulic acid 1, boropinic acid 2, 4'-geranyloxyferulic acid 3, umbelliferone 4, 7-isopentenyloxycoumarin 5, and auraptene 6, have been determined in Italian raw propolis after having been extracted with different methodologies. An aqueous solution of β-cyclodextrin was the best extraction method for ferulic acid 1, treatment with indifferently EtOH or aqueous β-cyclodextrin were the most effective one for umbelliferone 4, boropinic acid 2 gave the best yields either with H2O/β-cyclodextrin or olive oil treatment or in biphasic systems, maceration with biphasic mixtures of aqueous β-cyclodextrin and olive oil was seen to be the most effective procedure for 7-isopentenyloxycoumarin 5, the only method providing significant quantities of 4'-geranyloxyferulic acid 3 was the maceration of raw propolis with olive oil, and finally auraptene 4 was best extracted with absolute EtOH. "Classic" maceration in general performed better than ultrasound-assisted one. Copyright © 2016 Elsevier B.V. All rights reserved.

  9. Flavonoids from leaves of Mauritia flexuosa

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    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.

  10. 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

  11. Flavonoids in Inflammatory Bowel Disease: A Review

    Directory of Open Access Journals (Sweden)

    Teresa Vezza

    2016-04-01

    Full Text Available 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.

  12. 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.

  13. 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.

  14. 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)

  15. 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)

  16. [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.

  17. Quantitation of flavonoid constituents in citrus fruits.

    Science.gov (United States)

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

    1999-09-01

    Twenty-four flavonoids have been determined in 66 Citrus species and near-citrus relatives, grown in the same field and year, by means of reversed phase high-performance liquid chromatography analysis. Statistical methods have been applied to find relations among the species. The F ratios of 21 flavonoids obtained by applying ANOVA analysis are significant, indicating that a classification of the species using these variables is reasonable to pursue. Principal component analysis revealed that the distributions of Citrus species belonging to different classes were largely in accordance with Tanaka's classification system.

  18. 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.

  19. 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)

  20. 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).

  1. Acylated flavonol tri- and tetraglycosides in the flavonoid metabolome of Cladrastis kentukea (Leguminosae).

    Science.gov (United States)

    Kite, Geoffrey C; Rowe, Emily R; Lewis, Gwilym P; Veitch, Nigel C

    2011-04-01

    The foliar metabolome of Cladrastis kentukea (Leguminosae) contains a complex mixture of flavonoids including acylated derivatives of the 3-O-rhamnosyl(1→2)[rhamnosyl(1→6)]-galactosides of kaempferol and quercetin and their 7-O-rhamnosides, together with an array of non-acylated kaempferol and quercetin di-, tri- and tetraglycosides. Thirteen of the acylated flavonoids, 12 of which had not been reported previously, were characterised by spectroscopic and chemical methods. Eight of these were the four isomers of kaempferol 3-O-α-l-rhamnopyranosyl(1→2)[α-l-rhamnopyranosyl(1→6)]-(3/4-O-E/Z-p-coumaroyl-β-d-galactopyranoside) and their 7-O-α-l-rhamnopyranosides, and three were isomers of quercetin 3-O-α-l-rhamnopyranosyl(1→2)[α-l-rhamnopyranosyl(1→6)]-(3/4-O-E/Z-p-coumaroyl-β-d-galactopyranoside) - the remaining 4Z isomer was identified by LC-UV-MS analysis of a crude extract. The final two acylated flavonoids characterised by NMR were the 3E and 4E isomers of kaempferol 3-O-α-l-rhamnopyranosyl(1→2)[α-l-rhamnopyranosyl(1→6)]-(3/4-O-E-feruloyl-β-d-galactopyranoside)-7-O-α-l-rhamnopyranoside while the 3Z and 4Z isomers were again detected by LC-UV-MS. Using the observed fragmentation behaviour of the isolated compounds following a variety of MS experiments, a further 18 acylated flavonoids were given tentative structures by LC-MS analysis of a crude extract. Acylated flavonoids were absent from the flowers of C. kentukea, which contained an array of non-acylated kaempferol and quercetin glycosides. Immature fruits contained kaempferol 3-O-α-rhamnopyranosyl(1→2)[α-rhamnopyranosyl(1→6)]-β-galactopyranoside and its 7-O-α-rhamnopyranoside as the major flavonoids with acylated flavonoids, different from those in the leaves, only present as minor constituents. The presence of acylated flavonoids distinguishes the foliar flavonoid metabolome of C. kentukea from that of a closely related legume, Styphnolobium japonicum, which contains a similar

  2. Quantitative and Qualitative Analysis of Phenolic and Flavonoid Content in Moringa oleifera Lam and Ocimum tenuiflorum L.

    Science.gov (United States)

    Sankhalkar, Sangeeta; Vernekar, Vrunda

    2016-01-01

    Number of secondary compounds is produced by plants as natural antioxidants. Moringa oleifera Lam. and Ocimum tenuiflorum L. are known for their wide applications in food and pharmaceutical industry. To compare phenolic and flavonoid content in M. oleifera Lam and O. tenuiflorum L. by quantitative and qualitative analysis. Phenolic and flavonoid content were studied spectrophotometrically and by paper chromatography in M. oleifera Lam. and O. tenuiflorum L. Higher phenolic and flavonoid content were observed in Moringa leaf and flower. Ocimum flower showed higher phenolic content and low flavonoid in comparison to Moringa. Flavonoids such as biflavonyl, flavones, glycosylflavones, and kaempferol were identified by paper chromatography. Phytochemical analysis for flavonoid, tannins, saponins, alkaloids, reducing sugars, and anthraquinones were tested positive for Moringa and Ocimum leaf as well as flower. In the present study higher phenolic and flavonoid content, indicated the natural antioxidant nature of Moringa and Ocimum signifying their medicinal importance. Moringa oleifera Lam. and Ocimum tenuiflorum L. are widly grown in India and are known for their medicinal properties. Number of secondary metabolites like phenolics and flavonoids are known to be present in both the plants. The present study was conducted with an objective to qualitatively and quantitatively compare the phenolics and flavanoids in these two medicinally important plants.Quantitation of total phenolics and flavanoids was done by spectrophotometrically while qualitative analysis was perfomed by paper chromatography and by phytochemical tests. Our results have shown higher phenolics and flavanoid content in Moringa leaf and flower. However, higher phenolic content was absent in Ocimum flower compared to that of Moringa. Phytochemical analysis of various metabolites such as flavonoids, tanins, sapponins, alkaloids, anthraquinones revealed that both the plant extracts were rich sources of

  3. 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...

  4. 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

  5. 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

  6. 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 ...

  7. Lack of Prenylated Proteins, Autophagy Impairment and Apoptosis in SH-SY5Y Neuronal Cell Model of Mevalonate Kinase Deficiency

    Directory of Open Access Journals (Sweden)

    Paola Maura Tricarico

    2017-03-01

    Full Text Available Background/Aims: Mevalonate Kinase Deficiency (MKD, is a hereditary disease due to mutations in mevalonate kinase gene (MVK. MKD has heterogeneous clinical phenotypes: the correlation between MVK mutations and MKD clinical phenotype is still to be fully elucidated. Deficiency of prenylated proteins has been hypothesized as possible MKD pathogenic mechanism. Based on this hypothesis and considering that neurologic impairment characterizes Mevalonic Aciduria (MA, the most severe form of MKD, we studied the effects of I268T and N301T MVK mutations on protein prenylation, autophagy and programmed cell death in SH-SY5Y neuroblastoma cell lines. Methods: SH-SY5Y cells were transiently transfected, with the pCMV-6 plasmid containing MVK wild type and the two mutated sequences. Protein prenylation levels were evaluated using GFP-RhoA-F to assess farnesylation, and GFP-RhoA to evaluate geranylgeranylation; autophagy was measured by evaluating LC3 and p62 protein levels, while Annexin V-FITC and Propidium Iodide staining allowed apoptosis detection. Results: MVK mutants’ over-expression causes decreased levels of farnesylation and geranylgeranylation, and also increased LC3 lipidation in SH-SY5Y, with concomitant p62 accumulation. Treatment with bafilomycin A1 (an inhibitor of vacuolar H+-ATPase, a late autophagy inhibitor further increase LC3-II and p62 levels, suggesting that degradation of autophagolysosome could be impaired. SH-SY5Y, with both MVK mutants, showed apoptosis increase; the presence of N301T associated with augmented cell death. Conclusions: We hypothesize that mevalonate pathway impairment causes alteration of farnesylation and geranylgeranylation proteins and alteration of the autophagic flux; these changes can induce apoptosis, possibly more relevant in the presence of N301T mutation.

  8. Lack of Prenylated Proteins, Autophagy Impairment and Apoptosis in SH-SY5Y Neuronal Cell Model of Mevalonate Kinase Deficiency.

    Science.gov (United States)

    Tricarico, Paola Maura; Romeo, Alessandra; Gratton, Rossella; Crovella, Sergio; Celsi, Fulvio

    2017-01-01

    Mevalonate Kinase Deficiency (MKD), is a hereditary disease due to mutations in mevalonate kinase gene (MVK). MKD has heterogeneous clinical phenotypes: the correlation between MVK mutations and MKD clinical phenotype is still to be fully elucidated. Deficiency of prenylated proteins has been hypothesized as possible MKD pathogenic mechanism. Based on this hypothesis and considering that neurologic impairment characterizes Mevalonic Aciduria (MA), the most severe form of MKD, we studied the effects of I268T and N301T MVK mutations on protein prenylation, autophagy and programmed cell death in SH-SY5Y neuroblastoma cell lines. SH-SY5Y cells were transiently transfected, with the pCMV-6 plasmid containing MVK wild type and the two mutated sequences. Protein prenylation levels were evaluated using GFP-RhoA-F to assess farnesylation, and GFP-RhoA to evaluate geranylgeranylation; autophagy was measured by evaluating LC3 and p62 protein levels, while Annexin V-FITC and Propidium Iodide staining allowed apoptosis detection. MVK mutants' over-expression causes decreased levels of farnesylation and geranylgeranylation, and also increased LC3 lipidation in SH-SY5Y, with concomitant p62 accumulation. Treatment with bafilomycin A1 (an inhibitor of vacuolar H+-ATPase, a late autophagy inhibitor) further increase LC3-II and p62 levels, suggesting that degradation of autophagolysosome could be impaired. SH-SY5Y, with both MVK mutants, showed apoptosis increase; the presence of N301T associated with augmented cell death. We hypothesize that mevalonate pathway impairment causes alteration of farnesylation and geranylgeranylation proteins and alteration of the autophagic flux; these changes can induce apoptosis, possibly more relevant in the presence of N301T mutation. © 2017 The Author(s)Published by S. Karger AG, Basel.

  9. Inhibition of Prenylation Promotes Caspase 3 Activation, Lamin B Degradation and Loss in Metabolic Cell Viability in Pancreatic β-Cells

    Directory of Open Access Journals (Sweden)

    Khadija G. Syeda

    2017-10-01

    Full Text Available Background/Aims: Lamins are intermediate filament proteins that constitute the main components of the lamina underlying the inner-nuclear membrane and serve to organize chromatin. Lamins (e.g., lamin B undergo posttranslational modifications (e.g., isoprenylation at their C-terminal cysteine residues. Such modifications are thought to render optimal association of lamins with the nuclear envelop. Using human islets, rodent islets, and INS-1 832/13 cells, we recently reported significant metabolic defects under glucotoxic and endoplasmic reticulum (ER stress conditions, including caspase 3 activation and lamin B degradation. The current study is aimed at further understanding the regulatory roles of protein prenylation in the induction of the aforestated metabolic defects. Methods: Subcellular phase partitioning assay was done using Triton X-114. Cell morphology and metabolic cell viability assays were carried out using standard methodologies. Results: We report that exposure of pancreatic β-cells to Simvastatin, an inhibitor of mevalonic acid (MVA biosynthesis, and its downstream isoprenoid derivatives, or FTI-277, an inhibitor of farnesyltransferase that mediates farnesylation of lamins, leads to activation of caspase 3 and lamin B degradation. Furthermore, Simvastatin-treatment increased activation of p38MAPK (a stress kinase and inhibited ERK1/2 (regulator of cell proliferation. Inhibition of farnesylation also resulted in the release of degraded lamin B into the cytosolic fraction and promoted loss in metabolic cell viability. Conclusion: Based on these findings we conclude that protein prenylation plays key roles in islet β-cell function. These findings affirm further support to the hypothesis that defects in prenylation pathway induce caspase-3 activation and nuclear lamin degradation in pancreatic β-cells under the duress of metabolic stress (e.g., glucotoxicity.

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

    Directory of Open Access Journals (Sweden)

    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. Interactions Between Flavonoid-Rich Extracts and Sodium Caseinate Modulate Protein Functionality and Flavonoid Bioaccessibility in Model Food Systems.

    Science.gov (United States)

    Elegbede, Jennifer L; Li, Min; Jones, Owen G; Campanella, Osvaldo H; Ferruzzi, Mario G

    2018-05-01

    With growing interest in formulating new food products with added protein and flavonoid-rich ingredients for health benefits, direct interactions between these ingredient classes becomes critical in so much as they may impact protein functionality, product quality, and flavonoids bioavailability. In this study, sodium caseinate (SCN)-based model products (foams and emulsions) were formulated with grape seed extract (GSE, rich in galloylated flavonoids) and green tea extract (GTE, rich in nongalloylated flavonoids), respectively, to assess changes in functional properties of SCN and impacts on flavonoid bioaccessibility. Experiments with pure flavonoids suggested that galloylated flavonoids reduced air-water interfacial tension of 0.01% SCN dispersions more significantly than nongalloylated flavonoids at high concentrations (>50 μg/mL). This observation was supported by changes in stability of 5% SCN foam, which showed that foam stability was increased at high levels of GSE (≥50 μg/mL, P < 0.05) but was not affected by GTE. However, flavonoid extracts had modest effects on SCN emulsion. In addition, galloylated flavonoids had higher bioaccessibility in both SCN foam and emulsion. These results suggest that SCN-flavonoid binding interactions can modulate protein functionality leading to difference in performance and flavonoid bioaccessibility of protein-based products. As information on the beneficial health effects of flavonoids expands, it is likely that usage of these ingredients in consumer foods will increase. However, the necessary levels to provide such benefits may exceed those that begin to impact functionality of the macronutrients such as proteins. Flavonoid inclusion within protein matrices may modulate protein functionality in a food system and modify critical consumer traits or delivery of these beneficial plant-derived components. The product matrices utilized in this study offer relevant model systems to evaluate how fortification with flavonoid

  12. 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 ...

  13. [Contents of total flavonoids in Rhizoma Arisaematis].

    Science.gov (United States)

    Du, S S; Lin, H Y; Zhou, Y X; Wei, L X

    2001-06-01

    Comparing the contents of total flavonoides of Rhizoma Arisaematis, which collected in different time, regions, different varieties and processed. Determining the contents by ultraviolet spectro-photometry. The contents were found in the following sequence: 1. the end of July, the begin of July, August, September; 2. Beijing, Shanxi, Sichuan, Anhui; 3. Arisaema erubenscens, A. heterophyllum, A. amurense; 4. unprocessed product, processed product.

  14. 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 ...

  15. Flavonoids as Inhibitors of Human Butyrylcholinesterase Variants

    Directory of Open Access Journals (Sweden)

    Maja Katalinić

    2014-01-01

    Full Text Available The inhibition of butyrylcholinesterase (BChE, EC 3.1.1.8 appears to be of interest in treating diseases with symptoms of reduced neurotransmitter levels, such as Alzheimer’s disease. However, BCHE gene polymorphism should not be neglected in research since it could have an effect on the expected outcome. Several well-known cholinergic drugs (e.g. galantamine, huperzine and rivastigmine originating from plants, or synthesised as derivatives of plant compounds, have shown that herbs could serve as a source of novel target-directed compounds. We focused our research on flavonoids, biologically active polyphenolic compounds found in many plants and plant-derived products, as BChE inhibitors. All of the tested flavonoids: galangin, quercetin, fisetin and luteolin reversibly inhibited usual, atypical, and fluoride-resistant variants of human BChE. The inhibition potency increased in the following order, identically for all three BChE variants: luteolinflavonoids exists in view of BChE polymorphism. Our results suggested that flavonoids could assist the further development of new BChE-targeted drugs for treating symptoms of neurodegenerative diseases and dementia.

  16. 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 ...

  17. 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.

  18. Therapeutic potential of flavonoids in inflammatory bowel disease: A comprehensive review.

    Science.gov (United States)

    Salaritabar, Ali; Darvishi, Behrad; Hadjiakhoondi, Farzaneh; Manayi, Azadeh; Sureda, Antoni; Nabavi, Seyed Fazel; Fitzpatrick, Leo R; Nabavi, Seyed Mohammad; Bishayee, Anupam

    2017-07-28

    The inflammatory process plays a central role in the development and progression of numerous pathological situations, such as inflammatory bowel disease (IBD), autoimmune and neurodegenerative diseases, metabolic syndrome, and cardiovascular disorders. IBDs involve inflammation of the gastrointestinal area and mainly comprise Crohn's disease (CD) and ulcerative colitis (UC). Both pathological situations usually involve recurring or bloody diarrhea, pain, fatigue and weight loss. There is at present no pharmacological cure for CD or UC. However, surgery may be curative for UC patients. The prescribed treatment aims to ameliorate the symptoms and prevent and/or delay new painful episodes. Flavonoid compounds are a large family of hydroxylated polyphenolic molecules abundant in plants, including vegetables and fruits which are the major dietary sources of these compounds for humans, together with wine and tea. Flavonoids are becoming very popular because they have many health-promoting and disease-preventive effects. Most interest has been directed towards the antioxidant activity of flavonoids, evidencing a remarkable free-radical scavenging capacity. However, accumulating evidence suggests that flavonoids have many other biological properties, including anti-inflammatory, antiviral, anticancer, and neuroprotective activities through different mechanisms of action. The present review analyzes the available data about the different types of flavonoids and their potential effectiveness as adjuvant therapy of IBDs.

  19. Flavonoids in vegetable foods commonly consumed in Brazil and estimated ingestion by the Brazilian population.

    Science.gov (United States)

    Arabbi, Paola R; Genovese, Maria Inés; Lajolo, Franco M

    2004-03-10

    The objective of this work was to quantify the flavonoids present in foods most commonly consumed by the Brazilian population. The predominant flavonoids found in largest abundance in all of the analyzed vegetables were glycosides of quercetin. In lettuce, a small amount of luteolin was also detected. In sweet pepper, quercetin and luteolin were both present. White onion [48-56 mg/100 g of fresh weight (FW), expressed as aglycon], red onion (40-100 mg/100 g of FW), red lettuce (67-67.2 mg/100 g of FW), arugula (41-118 mg/100 g of FW), and chicory (18-38 mg/100 g of FW) were highest in total flavonoids. In fruits, the highest concentrations of flavonoids were found in the peel (125-170 mg/100 g of FW) and pulp (35-44 mg/100 g of FW) of oranges and in some apple varieties (14-36 mg/100 g of FW). Variability in flavonoid content due to time of harvesting was high for leafy vegetables and red onions. The estimated ingestion by Brazilian population ranged from 60 to 106 mg/day.

  20. Impact of certain flavonoids on lipid profiles--potential action of Garcinia cambogia flavonoids.

    Science.gov (United States)

    Koshy, A S; Vijayalakshmi, N R

    2001-08-01

    Flavonoids from Cocos nucifera, Myristica fragrance, Saraka asoka and Garcinia cambogia exerted hypolipidaemic activity in rats. Lipid lowering activity was maximum in rats administered flavonoids (10 mg/kg BW/day) from Garcinia cambogia. A dose response study revealed biphasic activity. Higher doses were less effective in reducing lipid levels in serum and tissues, although devoid of toxic effects. Copyright 2001 John Wiley & Sons, Ltd.

  1. 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.

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

    Directory of Open Access Journals (Sweden)

    Hongjie Feng

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

  3. Flavonoids and Strigolactones in Root Exudates as Signals in Symbiotic and Pathogenic Plant-Fungus Interactions

    Directory of Open Access Journals (Sweden)

    Horst Vierheilig

    2007-07-01

    Full Text Available Secondary plant compounds are important signals in several symbiotic and pathogenic plant-microbe interactions. The present review is limited to two groups of secondary plant compounds, flavonoids and strigolactones, which have been reported in root exudates. Data on flavonoids as signaling compounds are available from several symbiotic and pathogenic plant-microbe interactions, whereas only recently initial data on the role of strigolactones as plant signals in the arbuscular mycorrhizal symbiosis have been reported. Data from other plant-microbe interactions and strigolactones are not available yet. In the present article we are focusing on flavonoids in plant-fungalinteractions such as the arbuscular mycorrhizal (AM association and the signaling between different Fusarium species and plants. Moreover the role of strigolactones in the AM association is discussed and new data on the effect of strigolactones on fungi, apart from arbuscular mycorrhizal fungi (AMF, are provided.

  4. Potential ecological roles of flavonoids from Stellera chamaejasme.

    Science.gov (United States)

    Yan, Zhiqiang; Zeng, Liming; Jin, Hui; Qin, Bo

    2015-01-01

    Stellera chamaejasme L. (Thymelaeaceae), a perennial weed, distributes widely in the grasslands of Russia, Mongolia and China. The plant synthesizes various secondary metabolites including a group of flavonoids. To our knowledge, flavonoids play important roles in the interactions between plants and the environment. So, what are the benefits to S. chamaejasme from producing these flavonoids? Here, we discuss the potential ecological role of flavonoids from S. chamaejasme in protecting the plant from insects and other herbivores, as well as pathogens and competing plant species, and new data are provided on the phytotoxicity of flavonoids from S. chamaejasme toward Poa annua L.

  5. α-Glucosidase inhibition by flavonoids: an in vitro and in silico structure-activity relationship study.

    Science.gov (United States)

    Proença, Carina; Freitas, Marisa; Ribeiro, Daniela; Oliveira, Eduardo F T; Sousa, Joana L C; Tomé, Sara M; Ramos, Maria J; Silva, Artur M S; Fernandes, Pedro A; Fernandes, Eduarda

    2017-12-01

    α-Glucosidase inhibitors are described as the most effective in reducing post-prandial hyperglycaemia (PPHG) from all available anti-diabetic drugs used in the management of type 2 diabetes mellitus. As flavonoids are promising modulators of this enzyme's activity, a panel of 44 flavonoids, organised in five groups, was screened for their inhibitory activity of α-glucosidase, based on in vitro structure-activity relationship studies. Inhibitory kinetic analysis and molecular docking calculations were also applied for selected compounds. A flavonoid with two catechol groups in A- and B-rings, together with a 3-OH group at C-ring, was the most active, presenting an IC 50 much lower than the one found for the most widely prescribed α-glucosidase inhibitor, acarbose. The present work suggests that several of the studied flavonoids have the potential to be used as alternatives for the regulation of PPHG.

  6. 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

  7. Structure-activity relationships and molecular docking of thirteen synthesized flavonoids as horseradish peroxidase inhibitors.

    Science.gov (United States)

    Mahfoudi, Reguia; Djeridane, Amar; Benarous, Khedidja; Gaydou, Emile M; Yousfi, Mohamed

    2017-10-01

    For the first time, the structure-activity relationships of thirteen synthesized flavonoids have been investigated by evaluating their ability to modulate horseradish peroxidase (HRP) catalytic activity. Indeed, a modified spectrophotometrically method was carried out and optimized using 4-methylcatechol (4-MC) as peroxidase co-substrate. The results show that these flavonoids exhibit a great capacity to inhibit peroxidase with Ki values ranged from 0.14±0.01 to 65±0.04mM. Molecular docking has been achieved using Auto Dock Vina program to discuss the nature of interactions and the mechanism of inhibition. According to the docking results, all the flavonoids have shown great binding affinity to peroxidase. These molecular modeling studies suggested that pyran-4-one cycle acts as an inhibition key for peroxidase. Therefore, potent peroxidase inhibitors are flavonoids with these structural requirements: the presence of the hydroxyl (OH) group in 7, 5 and 4' positions and the absence of the methoxy (O-CH 3 ) group. Apigenin contributed better in HRP inhibitory activity. The present study has shown that the studied flavonoids could be promising HRP inhibitors, which can help in developing new molecules to control thyroid diseases. Copyright © 2017 Elsevier Inc. All rights reserved.

  8. 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.

  9. 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...

  10. 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)

  11. Curcumin, resveratrol and flavonoids as anti-inflammatory, cyto- and DNA-protective dietary compounds

    International Nuclear Information System (INIS)

    Bisht, Kavita; Wagner, Karl-Heinz; Bulmer, Andrew C.

    2010-01-01

    Numerous dietary compounds, ubiquitous in fruits, vegetables and spices have been isolated and evaluated during recent years for their therapeutic potential. These compounds include flavonoid and non-flavonoid polyphenols, which describe beneficial effects against a variety of ailments. The notion that these plant products have health promoting effects emerged because their intake was related to a reduced incidence of cancer, cardiovascular, neurological, respiratory, and age-related diseases. Exposure of the body to a stressful environment challenges cell survival and increases the risk of chronic disease developing. The polyphenols afford protection against various stress-induced toxicities through modulating intercellular cascades which inhibit inflammatory molecule synthesis, the formation of free radicals, nuclear damage and induce antioxidant enzyme expression. These responses have the potential to increase life expectancy. The present review article focuses on curcumin, resveratrol, and flavonoids and seeks to summarize their anti-inflammatory, cytoprotective and DNA-protective properties.

  12. Activity of flavonoids through λ sub max and electron cross-section

    International Nuclear Information System (INIS)

    Murthy, V.R.; Sreenivasulu, M.

    1997-01-01

    Flavonoids are widespread groups of natural constituents and present in the drugs in the form of mono or diglycosides. Being physiologically active, flavonoids are important in the field of pharmacological and clinical applications. Not many physical properties of flavonoids have been studied so far excepting UV and NMR studies. This paper deals with the evaluation of electron ionization cross section through λ sub max, a parameter available from UV studies. Electron ionization cross section was primarily conceived to be of use in radiation chemical data, mass spectroscopic and thermodynamic studies. But later attempts to correlate electron ionization cross-section with structural and related parameters prompted the authors to derive an explicit expression relating λ sub max and electron ionization cross-section (Q). The application of this method to correlate Q through λ sub max and interpret the results in terms of chemical activity are discussed

  13. Oroxylum indicum Seeds—Analysis of Flavonoids by Micellar Electrokinetic Chromatography

    Directory of Open Access Journals (Sweden)

    Anja Krüger

    2013-02-01

    Full Text Available Flavonoids are bioactive constituents in Oroxylum indicum seeds, an Asian traditional remedy used for the treatment of respiratory infections. In this study the first capillary electrophoretic method for their determination is presented. By using a 25 mM borax buffer at pH 9.2 containing 10 mM SDS as detergent, the determination of seven flavonoids was feasible in only 13 min. Method validation confirmed that the assay is in accordance with ICH requirements in respect to linearity, selectivity, sensitivity, accuracy and precision. Quantitative results revealed that baicalein-7-O-gentiobioside is the most abundant flavonoid in the drug (1.19 to 5.33%, followed by other baicalein derivatives (7-O-glucoside, 7-O-glucuronide. These observations were in good qualitative and quantitative agreement with LC-MS results.

  14. [Study on antioxidant activity of flavonoids from leaves of Psidium guajava].

    Science.gov (United States)

    Zhao, Yu-Jing; Li, Jian-Kuan; Zhang, Xin; Gao, Jian-Ping

    2018-02-01

    The present study is to study the chemical constituents from ethanol extract of Psidium guajava leaves. The constituents were separated and purified by silica gel column chromaiographios over, macroporous resin D-101, Sephadex LH-20, and ODS. Six flavonoids compounds were isolated and identified as quercetin(1), quercetin-3- O - α -D-arabinopyranoside(2), quercetin-3- O - α -D-ribopyranoside(3), quercetin-3- O - β -D-galactopyranoside(4), quercetin-3- O - α -D-glucopyranoside(5), and quercetin-3- O - α- D-xylpyranoside(6). The antioxidant effects of six flavonoids was evaluated by scavenging ability of DPPH, superoxide anion, ABTS·⁺, and reducing effect of Fe³⁺ as well as total antioxidant capacity(FRAP). Vitamin C was used as positive control. The results indicated that six flavonoids exhibited significant antioxidant effects. Copyright© by the Chinese Pharmaceutical Association.

  15. Study of the influence of ionizing radiation on the dynamics of accumulation of anthocyanins, flavonoids and carotenoids in individual organs of Alhagi Pseudalhagi

    International Nuclear Information System (INIS)

    Qojayeva, G.A.; Huseynova, M.Z.; Jafarov, E.S.; Babayev, Q.Q.

    2014-01-01

    Full text : It is known that the formation and accumulation of biologically active substances is a dynamic process. Their content varies in ontogeny plants and depending on environmental factors. In the present work it is studied the dynamics of accumulation of anthocyanins, flavonoids and carotenoids in certain organs of the plant in the budding phase. On the ability to accumulate flavonoids second place is occupied by the stem and flowers of the plant. In a certain amount of flavonoids are presented in plant seeds. In this case the roots of the plant show the least ability for accumulation of flavonoids. Regarding the role of radiation in the process, it should be noted that it plays a minor role in accumulation of flavonoids

  16. The ability of Abelmoschus manihot L. leaf extract in scavenging of free radical DPPH and total flavonoid determination

    Science.gov (United States)

    Sudewi, S.; Lolo, W. A.; Warongan, M.; Rifai, Y.; Rante, H.

    2017-11-01

    Abelmoschus manihot L. has reported to have flavonoids content. This study aims were to determine the ability of A. manihot extract in counteracting free radical DPPH and determine the content of total flavonoids. A. manihot leaf was taken from 2 regions in North Sulawesi, namely Tomohon and Kotamobagu. The maceration was carried out to extract the active compound in a 96% ethanol solvent. Free radical scavenging analysis was carried out by DPPH and determination of its total flavonoid in the extract was measured using spectrophotometri method. The results showed that A. manihot extract from Tomohon and Kotamobagu could counteract free radical of DPPH with value of free radical activity of 88.151 and 88.801 %, respectively. A. manihot leaf from Kotamobagu has higher total flavonoids content 61.763 mg/g compare to Tomohon 46.679 mg/g which presented as quercetin. A. manihot has antioxidant activity.

  17. Flavonoid content in leaf extracts of the fig (Ficus carica L.), carob (Ceratonia siliqua L.) and pistachio (Pistacia lentiscus L.).

    Science.gov (United States)

    Vaya, Jacob; Mahmood, Saeed

    2006-01-01

    The total flavonoid content of leaf extracts (70% ethanol) from fig (Ficus carica L.), carob (Ceratonia siliqua L.) and pistachio (Pistacia lentiscus L.) plants were determined by using reverse phase high-performance liquid chromatography (HPLC)-and analyzed by UV/VIS array and electrospray ionization (ESI)-mass spectrometry (MS) detectors. As a base for comparison, flavonoid type and level were also determined in extracts from soybeans and grape seeds. It was found that the major flavonoids in Ficus are quercetin and luteolin, with a total of 631 and 681 mg/kg extract, respectively. In Ceratonia leaves, nine different flavonoids were detected. The major one was myricetin (1486 mg/kg extract), with a similar level in Pistacia (1331 mg/kg extract, myricetin). The present study is the first to report the presence of the isoflavone genistein in the Pistacia leaf, which was discovered to consist of about a third of the genistein level detected in soybean.

  18. The oxidation of luteolin, the natural flavonoid dye

    International Nuclear Information System (INIS)

    Ramešová, Šárka; Sokolová, Romana; Tarábek, Ján; Degano, Ilaria

    2013-01-01

    The oxidation of natural flavonoid luteolin in aqueous solution is studied by electrochemical methods, electron paramagnetic resonance (EPR), spectroelectrochemistry and separation techniques HPLC-DAD and HPLC–MS/MS. The number of electrons involved in the oxidation of luteolin depends on the presence of its dissociation forms in solution. The study explains the differences in the number of electrons presented in the literature. The overall one electron oxidation mechanism of luteolin in alkaline solution is explained by the comproportionation reaction of resulting quinone, despite the fact that quinone is formed by two electron oxidation. Then a hydroxylation takes place. The EPR spectroelectrochemical study of the semiquinone radical anion formation as well as of the reaction steps following the electron transfer during the oxidation is presented. The novelty of this contribution consists in the additional temperature controlled semi-quantitative in situ EPR spectroelectrochemical experiment of the flavonoid oxidation. The data acquired by temperature controlled in situ EPR spectroelectrochemistry supports the comproportionation/disproportionation equilibria as well as the oxidative decomposition of luteolin and shows that the formation of a pi-dimer is less probable. The oxidation products hydroxy-luteolin and 3,5-dihydroxy-2-(2-oxoacetyl)phenyl-3,4-dihydroxybenzoate are not stable under ambient conditions and decompose to low molecular hydroxycompounds such as 3,4-dihydroxybenzoic acid and 2,5,7-trihydroxy-4H-1-benzopyran-4-one

  19. Protection of free-radical induced DNA strand breaks in vitro by flavonoids

    International Nuclear Information System (INIS)

    Fisher, L.; Anderson, R.F.

    1998-01-01

    Full text: We have used both plasmid and cosmid test systems to assay the effect of antioxidant flavonoids (AO) on DNA strand breakage in supercoiled closed circular DNA (DNA SC ) following the formation oxidative radical damage on DNA (DNA OXID + . ) in aqueous solution. Single strand breaks in DNA SC result in the formation of the relaxed circular form (DNA RC ) and double strand breaks give linear DNA (DNA L ). Dose response curves were constructed for the log of the loss of [DNA S C] against dose (0-600 Gy). The D 37 (dose for 37% unchanged DNA SC ) values determined in the presence of increasing amounts of flavonoids were compared as ratios to the D 37 control value to give dose modification factor (DMF). Irradiations were carried out under 'constant scavenging' conditions to separate out the effect of direct radical scavenging from the possible electron transfer reaction. Control irradiation experiments, were performed in aerated TRIS buffer, concentration 10 mM, which has a scavenging capacity, k s (defined as the summation of the rate constants for the reaction of OH radicals with all species in solution, multiplied by their concentrations) of 1.5 x 10 7 s -1 . The concentration of TRIS was reduced upon addition of AO to maintain k s at this level. Data will be presented for examples from all four major types of flavonoids (flavonols, isoflavones, flavones and flavon-3-ols) showing DMF values plateau at near 2.0 even at low concentrations (ca. 20 μM) of the flavonoids. Increased DNA strand breaks following post irradiation incubation with endo III protein was unaffected by having the flavonoids present at the time of irradiation. This result suggests that the protection afforded by the flavonoids is unlikely to be in repairing radical damage on pyrimidine bases that are precursors of DNA strand breaks. Overall these studies provide evidence for an additional mechanism of antioxidant activity

  20. 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...

  1. 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

  2. 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.

  3. 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.

  4. Determination of Total Phenolics, Flavonoids and Antioxidant Capacity of Methanolic Extracts of Some Brassica Seeds

    Directory of Open Access Journals (Sweden)

    Maria Doiniţa Borş

    2014-11-01

    Full Text Available Cruciferous vegetables are rich in nutrients and bioactive compounds. Seeds are highly nutritious and they are becoming more and more popular in nowadays diets. In the present study various types of radish and mustard seeds were evaluated on the basis of the total phenolic content (TPC, total flavonoid content (TFC and the antioxidant potential, using simple spectrophotometric methods.

  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. 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. 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.

  8. Flavonoids, flavonoid-rich foods, and cardiovascular risk: a meta-analysis of randomized controlled trials.

    Science.gov (United States)

    Hooper, Lee; Kroon, Paul A; Rimm, Eric B; Cohn, Jeffrey S; Harvey, Ian; Le Cornu, Kathryn A; Ryder, Jonathan J; Hall, Wendy L; Cassidy, Aedín

    2008-07-01

    The beneficial effects of flavonoid consumption on cardiovascular risk are supported by mechanistic and epidemiologic evidence. We aimed to systematically review the effectiveness of different flavonoid subclasses and flavonoid-rich food sources on cardiovascular disease (CVD) and risk factors--ie, lipoproteins, blood pressure, and flow-mediated dilatation (FMD). Methods included a structured search strategy on MEDLINE, EMBASE, and Cochrane databases; formal inclusion or exclusion, data extraction, and validity assessment; and meta-analysis. One hundred thirty-three trials were included. No randomized controlled trial studied effects on CVD morbidity or mortality. Significant heterogeneity confirmed differential effects between flavonoid subclasses and foods. Chocolate increased FMD after acute (3.99%; 95% CI: 2.86, 5.12; 6 studies) and chronic (1.45%; 0.62, 2.28; 2 studies) intake and reduced systolic (-5.88 mm Hg; -9.55, -2.21; 5 studies) and diastolic (-3.30 mm Hg; -5.77, -0.83; 4 studies) blood pressure. Soy protein isolate (but not other soy products or components) significantly reduced diastolic blood pressure (-1.99 mm Hg; -2.86, -1.12; 9 studies) and LDL cholesterol (-0.19 mmol/L; -0.24, -0.14; 39 studies). Acute black tea consumption increased systolic (5.69 mm Hg; 1.52, 9.86; 4 studies) and diastolic (2.56 mm Hg; 1.03, 4.10; 4 studies) blood pressure. Green tea reduced LDL (-0.23 mmol/L; -0.34, -0.12; 4 studies). For many of the other flavonoids, there was insufficient evidence to draw conclusions about efficacy. To date, the effects of flavonoids from soy and cocoa have been the main focus of attention. Future studies should focus on other commonly consumed subclasses (eg, anthocyanins and flavanones), examine dose-response effects, and be of long enough duration to allow assessment of clinically relevant endpoints.

  9. Effects and Mechanisms of Total Flavonoids from Blumea balsamifera (L. DC. on Skin Wound in Rats

    Directory of Open Access Journals (Sweden)

    Yuxin Pang

    2017-12-01

    spectrometry/diode array detector (UPLC-Q-TOF-MS/DAD, including 16 flavonoid aglucons, five flavonoid glycosides (main peaks in chromatogram, five chlorogenic acid analogs, and 1 coumarin. Reports show that flavonoid glycoside possesses therapeutic effects of curing wounds by inducing neovascularization, and chlorogenic acid also has anti-inflammatory and wound healing activities; we postulated that all the ingredients in total flavonoids sample maybe exert a synergetic effect on wound curing. Accompanied with detection of four growth factors, the upregulation of these key growth factors may be the mechanism of therapeutic activities of total flavonoids. The present study confirmed undoubtedly that flavonoids were the main active constituents that contribute to excisional wound healing, and suggested its action mechanism of improving expression levels of growth factors at different healing phases.

  10. Diploflavone, a New Flavonoid from Diplotropis ferruginea Benth. (Fabaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Almeida, Jackson Roberto G.S. [Universidade Federal do Vale do Sao Francisco, Petrolina, PE (Brazil); Barbosa-Filho, Jose Maria; Cabral, Analucia G.S.; Agra, Maria de Fatima; Silva, Marcelo S. da [Universidade Federal da Paraiba, Joao Pessoa, PB (Brazil). Lab. de Tecnologia Farmaceutica]. E-mail: jbarbosa@ltf.ufpb.br; Da Cunha, Emidio V. Leitao [Universidade Estadual da Paraiba, Campina Grande, PB (Brazil). Dept. de Farmacia; Nascimento, Silene C. do [Universidade Federal de Pernambuco, Recife, PE (Brazil). Dept. de Antibioticos; Braz-Filho, Raimundo [Universidade Estadual do Norte Fluminense (UENF), Campos dos Goytacases, RJ (Brazil). Setor de Quimica de Produtos Naturais. Lab. de Ciencias Quimicas

    2005-11-15

    The chemical examination of Diplotropis ferruginea Benth. resulted in the isolation of a new 3-methoxyflavone, 3-methoxy-6-O-prenyl-6,6-dimethylchromene-(7,8,2,3)-flavone, to which was given the trivial name diploflavone (1); as well as the known 3,6-dimethoxy-6,6- dimethylchromene-(7,8,2,3)-flavone (2). The structure of the new compound was established by spectral analyses. Cytotoxic activity of the isolated compounds was tested against the cells NClH292 (lung carcinoma), HEp-2 (larynx carcinoma) and KB (oral epidermoid carcinoma). The cells HEp-2 were the most affected by the substances tested. (author)

  11. Diploflavone, a New Flavonoid from Diplotropis ferruginea Benth. (Fabaceae)

    International Nuclear Information System (INIS)

    Almeida, Jackson Roberto G.S.; Barbosa-Filho, Jose Maria; Cabral, Analucia G.S.; Agra, Maria de Fatima; Silva, Marcelo S. da; Da Cunha, Emidio V. Leitao; Nascimento, Silene C. do; Braz-Filho, Raimundo

    2005-01-01

    The chemical examination of Diplotropis ferruginea Benth. resulted in the isolation of a new 3-methoxyflavone, 3-methoxy-6-O-prenyl-6 , 6 - dimethylchromene-(7,8,2 , 3 ) -flavone, to which was given the trivial name diploflavone (1); as well as the known 3,6-dimethoxy-6 , 6 - dimethylchromene-(7,8,2 , 3 ) -flavone (2). The structure of the new compound was established by spectral analyses. Cytotoxic activity of the isolated compounds was tested against the cells NClH292 (lung carcinoma), HEp-2 (larynx carcinoma) and KB (oral epidermoid carcinoma). The cells HEp-2 were the most affected by the substances tested. (author)

  12. Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations.

    Science.gov (United States)

    Arroyo-Currás, Netzahualcóyotl; Rosas-García, Víctor M; Videa, Marcelo

    2016-10-27

    Flavonoids are natural products commonly found in the human diet that show antioxidant, anti-inflammatory and anti-hepatotoxic activities. These nutraceutical properties may relate to the electrochemical activity of flavonoids. To increase the understanding of structure-electrochemical activity relations and the inductive effects that OH substituents have on the redox potential of flavonoids, we carried out square-wave voltammetry experiments and ab initio calculations of eight flavonoids selected following a systematic variation in the number of hydroxyl substituents and their location on the flavan backbone: three flavonols, three anthocyanidins, one anthocyanin and the flavonoid backbone flavone. We compared the effect that the number of -OH groups in the ring B of flavan has on the oxidation potential of the flavonoids considered, finding linear correlations for both flavonols and anthocyanidins ( R 2 = 0.98 ). We analyzed the effects that position and number of -OH substituents have on electron density distributions via ab initio quantum chemical calculations. We present direct correlations between structural features and oxidation potentials that provide a deeper insight into the redox chemistry of these molecules.

  13. Evaluation of flavonoids and diverse antioxidant activities of Sonchus arvensis

    Directory of Open Access Journals (Sweden)

    Khan Rahmat

    2012-10-01

    Full Text Available Abstract Background Sonchus arvensis is used in the treatment of various human aliments as a traditional medicine in Pakistan. In the study its various fractions are characterized for scavenging of diverse free radicals. Results Results of the present study revealed that various fractions of Sonchus arvensis significantly scavenged the free radicals (DPPH·, ABTS·+, ·OH, superoxide, however its methanolic fraction is more potent than other fractions. Significant correlation was found between DPPH·, ABTS·+, superoxide radical and total antioxidant activity with total flavonoids and phenolics contents. Phytochmical analysis revealed the presence kaempferol, quercetin, orientin, rutin, hyperoside, catechin and myricetin. Conclusion From the present data it is concluded that various fractions of Sonchus arvensis significantly scavenged the free radical, which might be due the presence of polyphenolic constituent.

  14. Commercial spices and industrial ingredients: evaluation of antioxidant capacity and flavonoids content for functional foods development

    Directory of Open Access Journals (Sweden)

    Marcela Roquim Alezandro

    2011-06-01

    Full Text Available The aim of this work was to evaluate spices and industrial ingredients for the development of functional foods with high phenolic contents and antioxidant capacity. Basil, bay, chives, onion, oregano, parsley, rosemary, turmeric and powdered industrial ingredients (β-carotene, green tea extract, lutein, lycopene and olive extract had their in vitro antioxidant capacity evaluated by means of the Folin-Ciocalteu reducing capacity and DPPH scavenging ability. Flavonoids identification and quantification were performed by High Performance Liquid Chromatography (HPLC. The results showed that spices presented a large variation in flavonoids content and in vitro antioxidant capacity, according to kind, brand and batches. Oregano had the highest antioxidant capacity and parsley had the highest flavonoid content. The industrial ingredient with the highest antioxidant capacity was green tea extract, which presented a high content of epigalocatechin gallate. Olive extract also showed a high antioxidant activity and it was a good source of chlorogenic acid. This study suggests that oregano, parsley, olive and green tea extract have an excellent potential for the development of functional foods rich in flavonoids as antioxidant, as long as the variability between batches/brands is controlled.

  15. 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.

  16. Flavonoids from the roots of Artocarpus heterophyllus.

    Science.gov (United States)

    Yuan, Wen-Jun; Yuan, Jin-Bin; Peng, Jia-Bing; Ding, Yuan-Qing; Zhu, Ji-Xiao; Ren, Gang

    2017-03-01

    Four new flavonoids, artoheteroids A-D (1-4), together with six known ones (5-10), were isolated from the roots of Artocarpus heterophyllus. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR, UV, IR, CD, and HR-ESI-MS. All isolated compounds were screened for their inhibitory abilities against cathepsin K (CatK). Among them, compounds 1-2, 4-6, and 10 were found to have suppression capabilities against CatK with IC 50 values ranging from 1.4 to 93.9μM. Copyright © 2017 Elsevier B.V. All rights reserved.

  17. 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)

  18. 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.

  19. 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.

  20. Psoralidin, a prenylated coumestan, as a novel anti-osteoporosis candidate to enhance bone formation of osteoblasts and decrease bone resorption of osteoclasts

    DEFF Research Database (Denmark)

    Zhai, Yuankun; Li, Yingying; Wang, Yanping

    2017-01-01

    Traditional Chinese medicines (TCM) have been proven to prevent osteoporosis, but their clinical applications are not widely recognized due to their complicated ingredients. Psoralidin, a prenylated coumestan, has been reported to prevent bone loss of ovariectomized rats, but detailed mechanisms...... and osteoclastic bone resorption, as demonstrated by the lower tartrate-resistant acid phosphatase activity and smaller area, with fewer resorption pits formed. Interestingly, psoralidin showed much stronger effects than coumestrol at enhancing osteoblast proliferation/differentiation or inhibiting osteoclast...... differentiation and bone resorption. Moreover, we found that both psoralidin and coumestrol suppressed COX-2 and ROS production in rat osteoblastic calvarias cells, and psoralidin showed stronger effects than coumestrol. Furthermore, we detected that by blocking estrogen receptors with ICI 182.780 (an estrogen...

  1. 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...

  2. FLAVONOIDS QUANTITATIVE DETERMINATION IN THE INFLORESCENCES OF TAGETES ERECTA AND TAGETES PATULA

    Directory of Open Access Journals (Sweden)

    Е. A. Malyugina

    2013-12-01

    Full Text Available INTRODUCTION The Genus marigold (Tagetes belongs to the family Asteraceae. The native land of this genus is the Central America. The genus marigold contains about 56 species and more than 600 forms and cultivars that are widely distributed around the world. The most distributed species are T. erecta L. and T. patula L. The chemical constituents of marigolds and their biological activity are intensively studied now. These plants contain more than 100 secondary metabolites, e.g. flavonoids, carotenoids, steroids, alkaloids, phenol derivate and others. The biological active carotenoids, flavonoids, essential oil, vitamins that contained in the inflorescences and herbs of Tagetes L. has anti-oxidant, anti-inflammatory, antibacterial and other activity. Tagetes L. genus plants widely used in traditional medicine as wound healing, hepatoprotective, choleretic, and adaptogenic medicines. The essential oil of marigolds has insecticidal properties and used in national economics. Also this plants are used in ophthalmology. The main biological active compounds of Tagetes L. are flavonoids. Composition of the most perspective carotenoid-contain species and cultivars of Tagetes L., such as T. patula nana L. (Gold Kopfen, Orangeflamme and T. erecta L. remains poorly understood. They need to be studied as perspective source of the biological active flavonoids. OBJECTIVE The aim of the study was to determine flavonoids contain in the inflorescences of Tagetes erecta L. cultivars “Equinox” and “Hawaii” and Tagetes patula L. cultivars “Gold Kopfen” and “Orangeflamme”. To determine the most perspective cultivars for obtaining the medicines. MATERIALS AND METHODS Tagetes patula L. and Tagetes erecta L. was selected in the present study. Plant material (inflorescences was collected from different regions of Ukraine. About 0.1 of crushed inflorescences was extracted by ethanol about 30 minutes twice, filtered and cooled. Appropriate quantities of

  3. Theoretical simulations on the antioxidant mechanism of naturally occurring flavonoid: A DFT approach

    International Nuclear Information System (INIS)

    Praveena, R.; Sadasivam, K.

    2016-01-01

    Synthetic antioxidants such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) are found to be toxic, hence non-carcinogenic naturally occurring radical scavengers especially flavonoids have gained considerable importance in the past two decades. In the present investigation, the radical scavenging activity of C-glycosyl flavonoids is evaluated using theoretical approach which could broaden its scope in therapeutic applications. Gas and solvent phase studies of structural and molecular characteristics of C-glycosyl flavonoid, isovitexin is investigated through hydrogen atom transfer mechanism (HAT), Electron transfer-proton transfer (ET–PT) and Sequential proton loss electron transfer (SPLET) by Density functional theory (DFT) using hybrid parameters. The computed values of the adiabatic ionization potential, electron affinity, hardness, softness, electronegativity and electrophilic index indicate that isovitexin possess good radical scavenging activity. The behavior of different –OH groups in polyphenolic compounds is assessed by considering electronic effects of the neighbouring groups and the overall geometry of molecule which in turn helps in analyzing the antioxidant capacity of the polyphenolic molecule. The studies indicate that the H–atom abstraction from 4’–OH site is preferred during the radical scavenging process. From Mulliken spin density analysis and FMOs, B–ring is found to be more delocalized center and capable of electron donation. Comparison of antioxidant activity of vitexin and isovitexin leads to the conclusion that isovitexin acts as a better radical scavenger. This is an evidence for the importance of position of glucose unit in the flavonoid.

  4. Total Phenolic, Flavonoids and Antioxidant Capacity of Some Medicinal and Aromatic Plants

    Directory of Open Access Journals (Sweden)

    Melinda Nagy

    2014-11-01

    Full Text Available Abstract: Antioxidants are substances that protect cells from the induced oxidative stress damage caused by unstable molecules known as free radicals that. Antioxidants neutralize free radicals as a natural by-product of normal cell processes. In the present study,were evaluated  the phenolic and flavonoids contents as well as the antioxidant capacity of seeds from  the Lamiaceae and Apiaceae family: fennel  (Foeniculum vulgare, dill (Anethum graveolens and rosemary (Rosmarinus officinalis . (Sreemoyee Ch. et. al., 2012 The main objective of the study was the comparative assessment of the phenolic and flavonoid compounds from dill, rosemary and fennel methanolic extracts correlated with their  antioxidant activity. Both total phenolic content and flavonoids content of the seeds samples were measured spectrophotometrically using the Folin-Ciocalteu assay and a chromogenic system of NaNO2–Al(NO33–NaOH, respectively.. Antioxidant capacity was determined by 2,2-DPPH method. Results strongly showed that Rosmarinus officinalis extract has the most effective antioxidant capacity in scavenging DPPH radicals, while Foeniculum vulgare and Anethum graveolens were less active. The total phenolic content was within 773,14 and 3367,24mg GAE/ 100g while the concentration in flavonoids was between 231,84 and 1325,53 QEg/100g dry seeds.  

  5. Bioactive Flavonoids, Antioxidant Behaviour, and Cytoprotective Effects of Dried Grapefruit Peels (Citrus paradisi Macf.)

    Science.gov (United States)

    Castro-Vazquez, Lucia; Alañón, María Elena; Rodríguez-Robledo, Virginia; Pérez-Coello, María Soledad; Hermosín-Gutierrez, Isidro; Díaz-Maroto, María Consuelo; Jordán, Joaquín; Galindo, María Francisca; Arroyo-Jiménez, María del Mar

    2016-01-01

    Grapefruit (Citrus paradisi Macf.) is an important cultivar of the Citrus genus which contains a number of nutrients beneficial to human health. The objective of the present study was to evaluate changes in bioactive flavonoids, antioxidant behaviour, and in vitro cytoprotective effect of processed white and pink peels after oven-drying (45°C–60°C) and freeze-drying treatments. Comparison with fresh grapefruit peels was also assessed. Significant increases in DPPH, FRAPS, and ABTS values were observed in dried grapefruit peel samples in comparison with fresh peels, indicating the suitability of the treatments for use as tools to greatly enhance the antioxidant potential of these natural byproducts. A total of thirteen flavonoids were quantified in grapefruit peel extracts by HPLC-MS/MS. It was found that naringin, followed by isonaringin, was the main flavonoid occurring in fresh, oven-dried, and freeze-dried grapefruit peels. In vivo assay revealed that fresh and oven-dried grapefruit peel extracts (45°C) exerted a strong cytoprotective effect on SH-SY5Y neuroblastoma cell lines at concentrations ranging within 0.1–0.25 mg/mL. Our data suggest that grapefruit (Citrus paradisi Macf.) peel has considerable potential as a source of natural bioactive flavonoids with outstanding antioxidant activity which can be used as agents in several therapeutic strategies. PMID:26904169

  6. Protective effects of fisetin and other berry flavonoids in Parkinson's disease.

    Science.gov (United States)

    Maher, Pamela

    2017-09-20

    Parkinson's disease (PD) is an age-associated degenerative disease of the midbrain that results from the loss of dopaminergic neurons in the substantia nigra. It initially presents as a movement disorder with cognitive and other behavioral problems appearing later in the progression of the disease. Current therapies for PD only delay the onset or reduce the motor symptoms. There are no treatments to stop the nerve cell death or to cure the disease. It is becoming increasingly clear that neurological diseases such as PD are multi-factorial involving disruptions in multiple cellular systems. Thus, it is unlikely that modulating only a single factor will be effective at either preventing disease development or slowing disease progression. A better approach is to identify small molecules that have multiple biological activities relevant to the maintenance of brain function. Flavonoids are polyphenolic compounds that are widely distributed in fruits and vegetables and therefore regularly consumed in the human diet. While flavonoids were historically characterized on the basis of their antioxidant and free radical scavenging effects, more recent studies have shown that flavonoids have a wide range of activities that could make them particularly effective as agents for the treatment of PD. In this article, the multiple physiological benefits of flavonoids in the context of PD are first reviewed. Then, the evidence for the beneficial effects of the flavonol fisetin in models of PD are discussed. These results, coupled with the known actions of fisetin, suggest that it could reduce the impact of PD on brain function.

  7. Concurrent synthesis and release of nod-gene-inducing flavonoids from alfalfa roots

    International Nuclear Information System (INIS)

    Maxwell, C.A.; Phillips, D.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- 14 C]-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 14 C. In the presence of AOPP, 14 C 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%. 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

  8. Theoretical simulations on the antioxidant mechanism of naturally occurring flavonoid: A DFT approach

    Energy Technology Data Exchange (ETDEWEB)

    Praveena, R. [Department of Chemistry, Bannari Amman Institute of Technology, Sathyamangalam, Erode, Tamil Nadu (India); Sadasivam, K. [Department of Physics, Bannari Amman Institute of Technology, Sathyamangalam, Erode, Tamil Nadu (India)

    2016-05-06

    Synthetic antioxidants such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) are found to be toxic, hence non-carcinogenic naturally occurring radical scavengers especially flavonoids have gained considerable importance in the past two decades. In the present investigation, the radical scavenging activity of C-glycosyl flavonoids is evaluated using theoretical approach which could broaden its scope in therapeutic applications. Gas and solvent phase studies of structural and molecular characteristics of C-glycosyl flavonoid, isovitexin is investigated through hydrogen atom transfer mechanism (HAT), Electron transfer-proton transfer (ET–PT) and Sequential proton loss electron transfer (SPLET) by Density functional theory (DFT) using hybrid parameters. The computed values of the adiabatic ionization potential, electron affinity, hardness, softness, electronegativity and electrophilic index indicate that isovitexin possess good radical scavenging activity. The behavior of different –OH groups in polyphenolic compounds is assessed by considering electronic effects of the neighbouring groups and the overall geometry of molecule which in turn helps in analyzing the antioxidant capacity of the polyphenolic molecule. The studies indicate that the H–atom abstraction from 4’–OH site is preferred during the radical scavenging process. From Mulliken spin density analysis and FMOs, B–ring is found to be more delocalized center and capable of electron donation. Comparison of antioxidant activity of vitexin and isovitexin leads to the conclusion that isovitexin acts as a better radical scavenger. This is an evidence for the importance of position of glucose unit in the flavonoid.

  9. Inhibition of fatty acid amide hydrolase by kaempferol and related naturally occurring flavonoids

    Science.gov (United States)

    Thors, L; Belghiti, M; Fowler, C J

    2008-01-01

    Background and purpose: Recent studies have demonstrated that the naturally occurring isoflavone compounds genistein and daidzein inhibit the hydrolysis of anandamide by fatty acid amide hydrolase (FAAH) in the low micromolar concentration range. The purpose of the present study was to determine whether this property is shared by flavonoids. Experimental approach: The hydrolysis of anandamide in homogenates and intact cells was measured using the substrate labelled in the ethanolamine part of the molecule. Key results: Twenty compounds were tested. Among the commonly occurring flavonoids, kaempferol was the most potent, inhibiting FAAH in a competitive manner with a Ki value of 5 μM. Among flavonoids with a more restricted distribution in nature, the two most active toward FAAH were 7-hydroxyflavone (IC50 value of 0.5–1 μM depending on the solvent used) and 3,7-dihydroxyflavone (IC50 value 2.2 μM). All three compounds reduced the FAAH-dependent uptake of anandamide and its metabolism by intact RBL2H3 basophilic leukaemia cells. Conclusions and implications: Inhibition of FAAH is an additional in vitro biochemical property of flavonoids. Kaempferol, 7-hydroxyflavone and 3,7-dihydroxyflavone may be useful as templates for the synthesis of novel compounds, which target several systems that are involved in the control of inflammation and cancer. PMID:18552875

  10. Chemoprevention of skin cancer by the flavonoid fraction of Saraca asoka.

    Science.gov (United States)

    Cibin, T R; Devi, D Gayathri; Abraham, Annie

    2010-05-01

    Saraca asoka (Family - Caesalpiniaceae) has been widely used in the Ayurvedic (traditional Indian) system of medicine especially due to its wound healing property. The present study investigated the chemopreventive property of flavonoids from the flowers of Saraca asoka on 7,12 dimethyl benz(a)anthracene (DMBA) induced skin cancer in mice models. A single topical application of DMBA (100 microg/50 microL of acetone) followed after 2 weeks by three times a week treatment with croton oil (1% in acetone), for 20 weeks resulted in tumor induction. The topical application of the flavonoid fraction of S. asoka (FF S. asoka), 30 min prior to the application of croton oil thrice weekly for 20 weeks, caused a significant reduction in the number of tumors per mouse and the percentage of tumor-bearing mice. Also the latency period for the appearance of the first tumor was delayed by S. asoka pretreatment. In the flavonoid fraction (5 mg and 10 mg/kg body weight) treated animals, the levels of biochemical markers - rhodanese, myeloperoxidase, beta-D-glucuronidase, sialic acid, hexokinase and caspase 3 were significantly restored to near normal levels. These findings suggest the chemopreventive activity of flavonoids from S. asoka on two stage skin carcinogenesis. Histological data also support the chemopreventive potential of S. asoka. Copyright (c) 2009 John Wiley & Sons, Ltd.

  11. Gastroprotective effects of flavonoids in plant extracts.

    Science.gov (United States)

    Zayachkivska, O S; Konturek, S J; Drozdowicz, D; Konturek, P C; Brzozowski, T; Ghegotsky, M R

    2005-03-01

    The purpose of this paper is to overview the relations between plant-originated substances and their bioactivity measured in terms of antioxidant, cytoprotective and antiulcer activities. In addition, we assessed whether these compounds are capable of affecting the gastric mucosal lesions induced by absolute ethanol applied intragastrically (i.g.). The following plant-originated flavonoid substances were considered; Solon (Sophoradin extract), Amaranth seed extract, grapefruit-seed extract (GSE) and capsaicin (extract of chilly pepper). The area of gastric mucosa lesions and gastric blood flow were measured in rats with ethanol-induced lesions without (control) and with one of the tested substances without and with capsaicin denervation of afferent nerves or administration of L-nitro-arginine (L-NNA), an inhibitor of nitric oxide synthase (NOS). Male Wistar rats, weighing 180-220 g fasted for 24 h before the study where used 100% ethanol was applied i.g. to induce gastric lesions, whose area was determined by planimetry. Gastric blood flow was assessed using electrolytic regional blood flowmeter. All tested plant-originated substances afforded gastroprotection against ethanol-induced damage and this was accompanied by increase in gastric microcirculation, both changes being reversed by pretreatment with neurotoxic dose of capsaicin or by pretreatment with L-NNA. We conclude that plant-originated flavonoid substances are highly gastroprotective probably due to enhancement of the expression of constitutive NOS and release of NO and neuropeptides such as calcitonin gene related peptide (CGRP) released from sensory afferent nerves increasing gastric microcirculation.

  12. 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.

  13. 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 ...

  14. 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.

  15. 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 ...

  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. 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

  18. Automated Annotation of Microbial and Human Flavonoid-Derived Metabolites

    NARCIS (Netherlands)

    Mihaleva, V.V.; Ünlü, F.; Vervoort, J.J.M.; Ridder, L.O.

    2015-01-01

    Flavonoids are a class of natural compounds essentially produced by plants that are part of animal and human diets and have assumed health-promoting benefits. Upon human consumption, these flavonoids are to a modest extent absorbed in the small intestines. The major part arrives in the colon where

  19. Metabolic engineering of yeast for fermentative production of flavonoids

    DEFF Research Database (Denmark)

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

    2017-01-01

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

  20. 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 ...

  1. 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 ...

  2. 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,

  3. 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…

  4. 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 ...

  5. Quantification and antibacterial activity of flavonoids in coffee samples

    African Journals Online (AJOL)

    Background: Flavonoids are the phenolic substances widely found in fruits, vegetables, grains, bark, roots, stems, flowers, tea and coffee. Methodology: In the current study quantity of flavonoids and antibacterial activities were determined in different coffee samples namely Nescafe classic, Nescafe gold, Nescafe martina, ...

  6. Flavonoids from Theobroma cacao down-regulate inflammatory mediators.

    Science.gov (United States)

    Ramiro, Emma; Franch, Angels; Castellote, Cristina; Pérez-Cano, Francisco; Permanyer, Joan; Izquierdo-Pulido, Maria; Castell, Margarida

    2005-11-02

    In the present study, we report the effects of a cocoa extract on the secretion and RNA expression of various proinflammatory mediators by macrophages. Monocyte chemoattractant protein 1 and tumor necrosis factor alpha (TNFalpha) were significantly and dose-dependently diminished by cocoa extract, and this effect was higher than that produced by equivalent concentrations of epicatechin but was lower than that produced by isoquercitrin. Interestingly, cocoa extract added prior to cell activation resulted in a significantly greater inhibition of TNFalpha secretion. Both cocoa extract and epicatechin decreased TNFalpha, interleukin (IL) 1alpha, and IL-6 mRNA expression, suggesting that their inhibitory effect on cytokine secretion is produced, in part, at the transcriptional level. Cocoa extract also significantly decreased NO secretion in a dose-dependent manner and with a greater effect than that produced by epicatechin. In conclusion, our study shows that cocoa flavonoids not only inhibit NO release from macrophages but also down-regulate inflammatory cytokines and chemokines.

  7. Effect of Sulfites on Antioxidant Activity, Total Polyphenols, and Flavonoid Measurements in White Wine.

    Science.gov (United States)

    Nardini, Mirella; Garaguso, Ivana

    2018-03-09

    Polyphenols content and antioxidant activity are directly related to the quality of wine. Wine also contains sulfites, which are added during the winemaking process. The present study aimed to evaluate the effects of sulfites on the assays commonly used to measure the antioxidant activity and polyphenols and flavonoids content of white wines. The effects of sulfites were explored both in the standard assays and in white wine. The addition of sulfites (at 1-10 μg) in the standard assays resulted in a significant, positive interference in the Folin-Ciocalteu's assay used for polyphenols measurements and in both the Ferric Reducing Antioxidant Power and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radical cation decolorization assays, which were used for antioxidant activity evaluation. A negative interference of sulfites (at 1-20 μg) was observed for the colorimetric aluminium-chloride flavonoids assay. The addition of sulfites to organic white wines (at 25-200 mg/L wine) clearly resulted in a significant overestimation of antioxidant activity and polyphenols content, and in an underestimation of flavonoids concentration. To overcome sulfite interferences, white wines were treated with cross-linked polyvinylpyrrolidone. The total polyphenols content and antioxidant activity measurements obtained after polyvinylpyrrolidone treatment were significantly lower than those obtained in the untreated wines. Flavonoids were expected to be higher after polyvinylpyrrolidone treatment, but were instead found to be lower than for untreated wines, suggesting that in addition to sulfites, other non-phenolic reducing compounds were present in white wine and interfered with the flavonoid assay. In view of our results, we advise that a purification procedure should be applied in order to evaluate the quality of white wine.

  8. Experimental Paper. Intrapopulation variability of flavonoid content in roots of Baikal skullcap (Scutellaria baicalensis Georgi

    Directory of Open Access Journals (Sweden)

    Kosakowska Olga

    2017-03-01

    Full Text Available Introduction: Baikal skullcap (Scutellaria baicalensis Georgi is an important medicinal plant, indigenous to Asia. Due to a wide range of pharmacological activities, its roots has been used for ages in Traditional Chinese Medicine. Recently, the species has become an object of interest of Western medicine, as well. Objective: The aim of the study was to determine the variability of Baikal skullcap population originated from Mongolia and cultivated in Poland, in terms of content and composition of flavonoids in the roots. Methods: The objects of the study were 15 individual plants, selected within examined population and cloned in order to obtain a sufficient amount of raw material. The total content of flavonoids in roots was determined according to Polish Pharmacopeia 6th. The qualitative analysis of flavonoids was carried out using HPLC, Shimadzu chromatograph. Results: The dry mass of roots ranged from 25.88 to 56.14 g × plant-1. The total content of flavonoids (expressed as a quercetin equivalent varied between 0.17 and 0.52% dry matter (DM. Nine compounds were detected within the group, with oroxylin A 7-Oglucuronide (346.90-1063.00 mg × 100 g-1 DM as a dominant, which differentiated investigated clones at the highest degree (CV=0.27. Baicalin (391.40-942.00 mg × 100 g-1 DM, wogonoside (324.00-641.10 mg × 100 g-1 DM and hesperetine 7-O-glucoside (163.00-346.32 mg × 100 g-1 DM were also present in a considerable amounts. Clone 7 was distinguished by the highest content of all investigated compounds, except wogonin and oroxylin A 7-O-glucuronide. Conclusions: Results obtained in present study show a high variability within Baical skullcap investigated population in respect of flavonoid compounds detected in roots. Thus, the results may be used in future investigations concerning the selection and breeding of this species.

  9. Isolated flavonoids from Ficus racemosa stem bark possess antidiabetic, hypolipidemic and protective effects in albino Wistar rats.

    Science.gov (United States)

    Keshari, Amit K; Kumar, Ghanendra; Kushwaha, Priya S; Bhardwaj, Monika; Kumar, Pranesh; Rawat, Atul; Kumar, Dinesh; Prakash, Anand; Ghosh, Balaram; Saha, Sudipta

    2016-04-02

    Ficus racemosa (FR) has been used for thousands of years in Ayurvedic system of medicine in India and is closely associated with prevention, treatment and cure of various human ailments like obesity and diabetes. It is popularly known as gular. A vast and wide range of chemical compounds like polyphenols, friedelane-type triterpenes, norfriedelane type triterpene, eudesmane-type sesquiterpene including various glycosides had been isolated from this plant. However, no detail studies related to isolation of flavonoids has been reported previously with their antidiabetic, hypolipidemic and toxicological consequences. The present study was undertaken to evaluate antidiabetic, hypolipidemic and toxicological assessments of flavonoids isolated from Ficus racemosa (FR) stem bark. We isolated four flavonoids from stem bark of FR and structures were confirmed by Infrared spectroscopy (IR), Nuclear Magnetic Resonance (NMR) (both 1D and 2D), mass spectroscopy (MS). Later, these flavonoids were administered to streptozotocin (STZ) rats once in a day for a period of seven days at 100mg/kg dose. We measured blood glucose level and body weight changes at different days (1st, 3rd, 5th and 7th days). Serum lipid profiles were also estimated to investigate the hypolipidemic potential of flavonoids in the similar experiment. Various oxidative stress parameters in pancreas and liver and hepatic biomarker enzymes in plasma were also determined to investigate the toxicity potential of isolated flavonoids. Finally, we performed docking studies to find out the mechanism of action. Our results collectively suggested that four flavonoids reduced blood glucose level and restored body weight, signifying antidiabetic action. There were reduction of other lipid profile parameters and increase of high density lipoprotein (HDL) during administration of flavonoids, also signifying hypolipidemic action. Various oxidative stress biomarkers and hepatic enzymes levels were also normalized with respect

  10. 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

  11. 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.

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

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    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

  13. 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)

  14. 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)

  15. 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)

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

    Energy Technology Data Exchange (ETDEWEB)

    Koes, R. E.; Quattrocchio, F.; Mol, J. N.M. [Department of Genetics, Institute for Molecular Biological Sciences, Vrije Universiteit, BioCentrum Amsterdam, De Boelelaan 1087, 1081HV, Amsterdam (Netherlands)

    1994-07-01

    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)

  17. A fluorescence quenching test for the detection of flavonoid transformation.

    Science.gov (United States)

    Schoefer, L; Braune, A; Blaut, M

    2001-11-13

    A novel fluorescence quenching test for the detection of flavonoid degradation by microorganisms was developed. The test is based on the ability of the flavonoids to quench the fluorescence of 1,6-diphenyl-1,3,5-hexatriene (DPH). Several members of the anthocyanidins, flavones, isoflavones, flavonols, flavanones, dihydroflavanones, chalcones, dihydrochalcones and catechins were tested with regard to their quenching properties. The anthocyanidins were the most potent quenchers of DPH fluorescence, while the flavanones, dihydroflavanones and dihydrochalcones, quenched the fluorescence only weakly. The catechins had no visible impact on DPH fluorescence. The developed test allows a quick and easy differentiation between flavonoid-degrading and flavonoid-non-degrading bacteria. The investigation of individual reactions of flavonoid transformation with the developed test system is also possible.

  18. Extraction, isolation and identification of flavonoid from Euphorbia neriifolia leaves

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    Veena Sharma

    2017-05-01

    Full Text Available The flavonoids contained in Euphorbia neriifolia leaves were extracted, identified and characterized. Direct and sequential soxhlet extraction and its concentrated fractions were subjected to thin layer chromatography and high performance thin layer chromatography. The results showed that maximum yield of the flavonoid (6.53 g was obtained from ethanolic extract. The Rf value of isolated flavonoid and phytochemical screening has been compared with standard Quercetin. Characterization of isolated flavonoid was done by IR, 1H NMR, and MS. On the basis of chemical and spectral analysis structure was elucidated as 2-(3,4-dihydroxy-5-methoxy-phenyl-3,5-dihydroxy-6,7-dimethoxychromen-4-one, a flavonoid. This compound was isolated for the first time from this plant.

  19. Evaluation of the antioxidant activity of extracts and flavonoids obtained from Bunium alpinum Waldst.

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    Lefahal Mostefa

    2017-03-01

    Full Text Available The aim of the present work was to evaluate the antioxidant activity of extracts and four flavonoids that had been isolated from the aerial parts of Bunium alpinum Waldst. et Kit. (Apiaceae and Tamarix gallica L. (Tamaricaceae. In this work, the four flavonoids were first extracted via various solvents, then purified through column chromatography (CC and thin layer chromatography (TLC. The four compounds were subsequently identified by spectroscopic methods, including: UV, mass spectrum 1H NMR and 13C NMR. The EtOAc extract of Bunium alpinum Waldst. et Kit yielded quercetin-3-O-β-glucoside (3’,4’,5,7-Tetrahydroxyflavone-3-β-D-glucopyranoside (1, while the EtOAc and n-BuOH extracts of Tamarix gallica L. afforded 3,5,3’-trihydroxy-7,4’-dimethoxyflavone (2, 3,5,7-trihydroxy-4’-methoxyflavone (3 and 5-hydroxy-3,7,4’-trimethoxyflavone (4. The antioxidant activity of the extracts and the flavonoids were then evaluated through DPPH free radical-scavenging assay. Of all studied extracts, the n-Butanol extract of Bunium alpinum (EC50 = 1.84 μg/ml showed the best antioxidant activity against (DPPH. In contrast, the isolates demonstrated varying degrees of antioxidant activity: compound (1 was the more active (EC50 = 0.28 μg/ml, followed by compound (3 and (2 (EC50 = 0.309μg/ml, EC50 = 0.406 μg/ml, respectively, compound (4 showed the lowest activity. All the isolated flavonoids exhibited antioxidant activity, but this was lower than the control (Trolox. In conclusion, due to the presence of flavonoids in their ariel parts, the studied plants could be natural sources of several important antioxidant agents

  20. DNA and Flavonoids Leach out from Active Nuclei of Taxus and Tsuga after Extreme Climate Stresses

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    Walter Feucht

    2015-09-01

    Full Text Available Severe over-stresses of climate caused dramatic changes in the intracellular distribution of the flavonoids. This was studied in needles from the current year’s growth of the following species and varieties: Tsuga canadensis, Taxus baccata, T. aurea, T. repens, T. nana, and T. compacta. The mode of steady changes in flavonoids was evaluated by microscopic techniques. Most of the flavonoids stain visibly yellow by themselves. The colorless flavanol subgroup can be stained blue by the DMACA reagent. In mid-summer 2013, outstanding high temperatures and intense photo-oxidative irradiation caused in a free-standing tree of Taxus baccata dramatic heat damage in a limited number of cells of the palisade layers. In these cells, the cytoplasm was burned brown. However, the nucleus maintained its healthy “blue” colored appearance which apparently was a result of antioxidant barrier effects by these flavanols. In late May 2014, excessive rainfall greatly affected all study trees. Collectively, in all study trees, a limited number of the mesophyll nuclei from the needless grown in 2013 and 2014 became overly turgid, enlarged in size and the flavanols leached outward through the damaged nuclear membranes. This diffusive stress event was followed one to three days later by a similar efflux of DNA. Such a complete dissolution of the nuclei in young tissues was the most spectacular phenomenon of the present study. As a common feature, leaching of both flavanols and DNA was markedly enhanced with increasing size and age of the cells. There is evidence that signalling flavonoids are sensitized to provide in nuclei and cytoplasm multiple mutual protective mechanisms. However, this well-orchestrated flavonoid system is broken down by extreme climate events.

  1. Flavonoids: hemisynthesis, reactivity, characterization and free radical scavenging activity.

    Science.gov (United States)

    Es-Safi, Nour-Eddine; Ghidouche, Souhila; Ducrot, Paul Henri

    2007-09-26

    Phenolic compounds form one of the main classes of secondary metabolites. They display a large range of structures and they are responsible for the major organoleptic characteristics of plant-derived-foods and beverages, particularly color and taste properties and they also contribute to the nutritional qualities of fruits and vegetables. Phenolic compounds are also highly unstable compounds which undergo numerous enzymatic and chemical reactions during postharvest food storage and processing thus adding to the complexity of plant polyphenol composition. Among these compounds flavonoids constitute one of the most ubiquitous groups of all plant phenolics. Owing to their importance in food organoleptic properties and in human health, a better understanding of their structures, their reactivity and chemical properties in addition to the mechanisms generating them appears essential to predict and control food quality. The purpose of this work is an overview of our findings concerning the hemisynthesis, the reactivity and the enzymatic oxidation of some flavonoids and shed light on the mechanisms involved in some of these processes and the structures of the resulting products. The free radical scavenging activity of some of the synthesized compounds is also presented and a structure-activity relationship is discussed. The first part of this review concerns the synthesis and structural characterization of modified monomeric flavanols. The use of these compounds as precursor for the preparation of natural and modified dimeric procyanidin derivatives was then explored through different coupling reactions. The full characterization of the synthesized compounds was achieved by concerted use of NMR and ESI-MS techniques. The free radical scavenging activity of some of the synthesized compounds was investigated. The second part of this review concerns the enzymatic oxidation of several flavonols by Trametes versicolor laccase. Most of the major oxidation products have been

  2. Flavonoids: Hemisynthesis, Reactivity, Characterization and Free Radical Scavenging Activity

    Directory of Open Access Journals (Sweden)

    Paul Henri Ducrot

    2007-09-01

    Full Text Available Phenolic compounds form one of the main classes of secondary metabolites. They display a large range of structures and they are responsible for the major organoleptic characteristics of plant-derived-foods and beverages, particularly color and taste properties and they also contribute to the nutritional qualities of fruits and vegetables. Phenolic compounds are also highly unstable compounds which undergo numerous enzymatic and chemical reactions during postharvest food storage and processing thus adding to the complexity of plant polyphenol composition. Among these compounds flavonoids constitute one of the most ubiquitous groups of all plant phenolics. Owing to their importance in food organoleptic properties and in human health, a better understanding of their structures, their reactivity and chemical properties in addition to the mechanisms generating them appears essential to predict and control food quality. The purpose of this work is an overview of our findings concerning the hemisynthesis, the reactivity and the enzymatic oxidation of some flavonoids and shed light on the mechanisms involved in some of these processes and the structures of the resulting products. The free radical scavenging activity of some of the synthesized compounds is also presented and a structure-activity relationship is discussed. The first part of this review concerns the synthesis and structural characterization of modified monomeric flavanols. The use of these compounds as precursor for the preparation of natural and modified dimeric procyanidin derivatives was then explored through different coupling reactions. The full characterization of the synthesized compounds was achieved by concerted use of NMR and ESI-MS techniques. The free radical scavenging activity of some of the synthesized compounds was investigated. The second part of this review concerns the enzymatic oxidation of several flavonols by Trametes versicolor laccase. Most of the major oxidation

  3. Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC.

    Science.gov (United States)

    Wang, Yuan-Chuen; Yang, Yi-Shan

    2007-05-01

    Numerous bioactive compounds are present in licorice (Glycyrrhizae Radix), including flavonoids and triterpenoids. In this study, a reversed-phase high-performance liquid chromatography (HPLC) method for simultaneous quantification of three flavonoids (liquiritin, liquiritigenin and isoliquiritigenin) and four triterpenoids (glycyrrhizin, 18alpha-glycyrrhetinic acid, 18beta-glycyrrhetinic acid and 18beta-glycyrrhetinic acid methyl ester) from licorice was developed, and further, to quantify these 7 compounds from 20 different licorice samples. Specifically, the reverse-phase HPLC was performed with a gradient mobile phase composed of 25 mM phosphate buffer (pH 2.5)-acetonitrile featuring gradient elution steps as follows: 0 min, 100:0; 10 min, 80:20; 50 min, 70:30; 73 min, 50:50; 110 min, 50:50; 125 min, 20:80; 140 min, 20:80, and peaks were detected at 254 nm. By using our technique, a rather good specificity was obtained regarding to the separation of these seven compounds. The regression coefficient for the linear equations for the seven compounds lay between 0.9978 and 0.9992. The limits of detection and quantification lay in the range of 0.044-0.084 and 0.13-0.25 microg/ml, respectively. The relative recovery rates for the seven compounds lay between 96.63+/-2.43 and 103.55+/-2.77%. Coefficient variation for intra-day and inter-day precisions lay in the range of 0.20-1.84 and 0.28-1.86%, respectively. Based upon our validation results, this analytical technique is a convenient method to simultaneous quantify numerous bioactive compounds derived from licorice, featuring good quantification parameters, accuracy and precision.

  4. Determination of flavonoids, polyphenols and antioxidant activity of Tephrosia purpurea: a seasonal study.

    Science.gov (United States)

    Pandey, Madan Mohan; Khatoon, Sayyada; Rastogi, Subha; Rawat, Ajay Kumar Singh

    2016-11-01

    Tephrosia purpurea (Linn · ) Pers. is widely used in traditional medicine to treat liver disorders, febrile attacks, enlargement and obstruction of liver, spleen, and kidney. In the present study, investigations were carried out to determine the seasonal impact on the content of flavonoid glycosides and on antioxidant activities so as to identify the optimal time of harvesting. The plant materials were collected in different seasons during 2013-2014. Air-dried, powdered plant materials were extracted with 95% ethanol and ethanol: water (1:1) by ultrasound-assisted extraction process. Their chemical composition in terms of total polyphenol and flavonoid contents (TPCs and TFCs) was determined using modified colorimetric Folin-Ciocalteu method and aluminum chloride colorimetric assay respectively. To determine the in vitro antioxidant activity, diphenyl-picryl hydrazyl (DPPH) radical-scavenging assay and total antioxidant capacity by phosphomolybdate antioxidant assay were carried out. High-performance liquid chromatography (HPLC)/photo-diode array (PDA) analysis was used to quantify the flavonoid glycosides in the samples collected in different seasons. Correlation studies were also carried out between antioxidant activities and TPCs. The highest TPC and TFC were found to be in the 95% ethanolic extract of the August sample and the lowest in the 50% hydro-alcoholic extract of the plant sample collected in winter season. It was observed that in both the assays used to determine the antioxidant activity, the 95% ethanolic extracts in all the seasons showed a higher activity than their respective 50% hydro-alcoholic extracts with an increase in activity as we go from cold to hot to rainy seasons. Based on correlation analysis, DPPH radical-scavenging activities as well as the spectrophotometrically measured phosphomolybdenum complex were also strongly correlated with TPC of the extracts. The most abundant flavonoid glycoside was quercetin-3-O-rhamnoglucoside in all

  5. [Studies on the flavonoids from Dendranthema lavandulifolium].

    Science.gov (United States)

    Shen, Y X; Quan, L H; Guan, L; Chen, J M

    1997-06-01

    From the whole plant of Dendranthema lavandulifolium, two flavonoides (I, II) and two flavone glycosides (III, IV) were isolated. They were identified as luteolin (I), apigenin (II), 5-hydroxy-4'-methoxy-flavone-7-O-alpha-L-rhamnopyranosyl(1-->6)-beta- D-glucopyranosyl (acaciin III) and 5-hydroxy-4'-methoxy-flavone-7-O-alpha-L-rhamnopyranosyl (1-->6) [2-O-acetyl-beta-D-glucopyranosyl(1-->2)]-beta-D-glucopyranoside (IV) by means of IR, UV, 1H-NMR, 13C-NMR, EI-MS, HRFAB, etc. Among these four compounds, I, II were isolated for the first time from this plant, IV is a new compound.

  6. Phytotoxic activity of flavonoids from Dicranostyles ampla.

    Science.gov (United States)

    Castro, Amaya; Cantrell, Charles L; Hale, Amber L; Duke, Stephen O

    2010-08-01

    Crude extracts from over 16 species of plants from the family Convolvulaceae were evaluated for phytotoxic activity against Agrostis stolonifera (bentgrass) and Lactuca sativa (lettuce) at 1000 microg/mL. Ethanol extracts of Dicranostyles ampla Ducke were among the most active of those species tested. Systematic bioassay-guided fractionation of the ethanol extract of the aerial parts from this species was performed to identify specifically the phytotoxic compounds. Two phytotoxic flavonoids, dihydromyricetin (1) and myricetin-3-O-alpha-rhamnoside or myricetrin (2), were found to be responsible for much of the activity of the extract as a whole in the A. stolonifera and L. sativa bioassay. In a Lemna paucicostata bioassay, 1 and 2 had no activity at 100 microM.

  7. Bio-effectiveness of the main flavonoids of Achillea millefolium in the pathophysiology of neurodegenerative disorders- a review

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    Fatemeh Ayoobi

    2017-06-01

    Full Text Available The Achillea millefolium L. (Yarrow is a common herb which is widely being used, worldwide. Achillea is being used for treatment of many disorders since centuries. It is considered safe for supplemental use and flavonoids such as kaempferol, luteolin and apigenin are of main constituents present in Achillea. Most of both antioxidant and anti-inflammatory properties of this herb have been attributed to its flavonoid content. Oxidative and inflammatory processes play important roles in pathogenesis of neurodegenerative diseases. Present review was aimed to review the latest literature evidences regarding application of Achillea and/or its three main flavonoid constituents on epilepsy, Alzheimer's disease, multiple sclerosis, Parkinson's disease and stroke.

  8. 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.

  9. 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.

  10. Dietary Flavonoids and Gastric Cancer Risk in a Korean Population

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    Hae Dong Woo

    2014-11-01

    Full Text Available Gastric cancer is the most common cancer among men in Korea, and dietary factors are closely associated with gastric cancer risk. We performed a case-control study using 334 cases and 334 matched controls aged 35–75 years. Significant associations were observed in total dietary flavonoids and their subclasses, with the exception of anthocyanidins and isoflavones (OR (95% CI: 0.49 (0.31–0.76, p trend = 0.007 for total flavonoids. However, these associations were not significant after further adjustment for fruits and vegetable consumption (OR (95% CI: 0.62 (0.36–1.09, p trend = 0.458 for total flavonoids. Total flavonoids and their subclasses, except for isoflavones, were significantly associated with a reduced risk gastric cancer in women (OR (95% CI: 0.33 (0.15–0.73, p trend = 0.001 for total flavonoids but not in men (OR (95% CI: 0.70 (0.39–1.24, p trend = 0.393 for total flavonoids. A significant inverse association with gastric cancer risk was observed in flavones, even after additional adjustment for fruits and vegetable consumption in women. No significantly different effects of flavonoids were observed between H. pylori-positive and negative subjects. In conclusion, dietary flavonoids were inversely associated with gastric cancer risk, and these protective effects of dietary flavonoids were prominent in women. No clear differences were observed in the subgroup analysis of H. pylori and smoking status.

  11. An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers

    NARCIS (Netherlands)

    Schutte, M.E.; Freidig, A.P.; Sandt, J.J.M. van de; Alink, G.M.; Rietjens, I.M.C.M.; Groten, J.P.

    2006-01-01

    The present study describes the effect of different flavonoids on the absorption of the pro-carcinogen PhIP through Caco-2 monolayers and the development of an in silico model describing this process taking into account passive diffusion and active transport of PhIP. Various flavonoids stimulated

  12. Flavonoid Composition and Biological Activities of Ethanol Extracts of Caryocar coriaceum Wittm., a Native Plant from Caatinga Biome

    Directory of Open Access Journals (Sweden)

    Daniela Ribeiro Alves

    2017-01-01

    Full Text Available Caryocar coriaceum fruits, found in Brazilian Cerrado and Caatinga, are commonly used as food and in folk medicine, as anti-inflammatory, bactericide, fungicide, leishmanicide, and nematicide. Due to the biological potential of this plant, this study focuses on the evaluation of antifungal and antileishmanial activities, including anticholinesterase and antioxidant tests, correlating with total phenols and flavonoids content. Peel extracts contain higher yield of phenols and flavonoids as analyzed by spectrophotometric methods. HPLC analysis of flavonoids revealed that isoquercitrin is the main flavonoid in both parts of the fruit, and peel extract showed the best antioxidant activity. In the inhibition of the acetylcholinesterase assay, both extracts demonstrate action comparable to physostigmine. The antimicrobial activity of extracts was evaluated against strains of Malassezia sp. and Microsporum canis, using the broth microdilution technique, in which the extracts showed similar MIC and MFC. The extracts present antileishmanial activity and low toxicity on murine macrophages and erythrocytes. Therefore, these results suggest a potential for the application of C. coriaceum fruit’s ethanol extracts in the treatment against dermatophyte fungi and leishmaniasis, probably due to the presence of active flavonoids. Further in vivo studies are recommended aiming at the development of possible new pharmaceutical compounds.

  13. Identification of phenolic acids and flavonoids in monofloral honey from Bangladesh by high performance liquid chromatography: determination of antioxidant capacity.

    Science.gov (United States)

    Moniruzzaman, Mohammed; Yung An, Chua; Rao, Pasupuleti Visweswara; Hawlader, Mohammad Nurul Islam; Azlan, Siti Amirah Binti Mohd; Sulaiman, Siti Amrah; Gan, Siew Hua

    2014-01-01

    The aim of the present study was to characterize the phenolic acids, flavonoids, and antioxidant properties of monofloral honey collected from five different districts in Bangladesh. A new high performance liquid chromatography (HPLC) equipped with a UV detector method was developed for the identification of the phenolic acids and flavonoids. A total of five different phenolic acids were identified, with the most abundant being caffeic acid, benzoic acid, gallic acid, followed by chlorogenic acid and trans-cinnamic acid. The flavonoids, kaempferol, and catechin were most abundant, followed by myricetin and naringenin. The mean moisture content, total sugar content, and color characteristics of the honey samples were 18.36 ± 0.95%, 67.40 ± 5.63 g/100 g, and 129.27 ± 34.66 mm Pfund, respectively. The mean total phenolic acids, total flavonoid content, and proline content were 199.20 ± 135.23, 46.73 ± 34.16, and 556.40 ± 376.86 mg/kg, respectively, while the mean FRAP values and DPPH radical scavenging activity were 327.30 ± 231.87 μM Fe (II)/100 g and 36.95 ± 20.53%, respectively. Among the different types of honey, kalijira exhibited the highest phenolics and antioxidant properties. Overall, our study confirms that all the investigated honey samples are good sources of phenolic acids and flavonoids with good antioxidant properties.

  14. Physiological Studies on Pea Tendrils. IV. Flavonoids and Contact Coiling

    Science.gov (United States)

    Jaffe, M. J.; Galston, A. W.

    1967-01-01

    Pea tendrils contain high concentrations of flavonoids, mainly quercetin-triglucosyl-p-coumarate (QGC). QGC is most abundant near the highly responsive apex of the tendril, and least abundant at the base. After mechanical stimulation, and during coiling of the tendril, the QGC titer drops to about 30% of its original value. The kinetics of flavonoid disappearance are significantly correlated with the kinetics of coiling. Aqueous extracts of unstimulated pea tendrils or 10 μm QGC inhibit contact coiling of excised tendrils. Extracts of coiled tendrils do not. The evidence indicates a possible regulatory role for flavonoids in contact coiling. PMID:16656581

  15. 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.

  16. Flavonoids in Helichrysum pamphylicum inhibit mammalian type I DNA topoisomerase.

    Science.gov (United States)

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

    2008-01-01

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

  17. Intrinsic bitterness of flavonoids and isoflavonoids and masking of their taste activity

    NARCIS (Netherlands)

    Roland, W.S.U.

    2014-01-01

    Many flavonoids and isoflavonoids have been associated with beneficial health effects. Therefore, consumption of (iso)flavonoid-rich food products, and enrichment of foods with (iso)flavonoids is becoming increasingly popular. However, several (iso)flavonoids have been reported as bitter.

  18. Oral prenylation inhibition with lonafarnib in chronic hepatitis D infection: a proof-of-concept randomised, double-blind, placebo-controlled phase 2A trial

    Science.gov (United States)

    Koh, Christopher; Canini, Laetitia; Dahari, Harel; Zhao, Xiongce; Uprichard, Susan L; Haynes-Williams, Vanessa; Winters, Mark A; Subramanya, Gitanjali; Cooper, Stewart L; Pinto, Peter; Wolff, Erin F; Bishop, Rachel; Han, Ma Ai Thanda; Cotler, Scott J; Kleiner, David E; Keskin, Onur; Idilman, Ramazan; Yurdaydin, Cihan; Glenn, Jeffrey S; Heller, Theo

    2015-01-01

    Summary Background Therapies for chronic hepatitis delta virus (HDV) infection are unsatisfactory. Prenylation is essential for HDV and inhibition abrogates HDV production in experimental models. In a proof-of-concept study, we aimed to assess the effect on HDV RNA levels, safety, and tolerability of the prenylation inhibitor lonafarnib in patients with chronic delta hepatitis. Methods In this phase 2A double-blind, randomised, placebo-controlled study, patients aged 18 years or older with chronic HDV infection were randomly assigned (3:1 in group 1 and 2:1 in group 2) to receive lonafarnib 100 mg (group 1) or lonafarnib 200 mg (group 2) twice daily for 28 days with 6 months’ follow-up. Participants were randomised by random-number tables blocked in groups of four without stratification. Both groups enrolled six treatment participants and two placebo participants. Group 1 placebo patients received open-label lonafarnib as group 2 participants. The primary therapeutic endpoint was a decrease in HDV RNA viral titre in serum and the primary safety endpoint was the ability to tolerate the drug at the prescribed dose for the full 4-week duration, defined as drug discontinuation due to intolerance or grade 3/4 adverse events. This trial is registered with ClinicalTrials.gov, number NCT01495585. Findings Between Jan 19, 2012, and April 28, 2014, 14 patients were enrolled, of whom eight were assigned to group 1 and six were assigned to group 2. At day 28, compared with placebo, mean log HDV RNA declines from baseline were −0.73 log IU/mL in group 1 (95% CI 0.17–1.31; p=0.03) and −1.54 log IU/mL in group 2 (1.21–1.93; p<0.0001). Lonafarnib serum concentrations correlated with HDV RNA change (r2=0.78, p<0.0001). Model fits show that hepatitis B surface antigen (HBsAg) remained stable after a short pharmacological delay (0.75 days [SE 0.24]), lonafarnib effectiveness in blocking HDV production was greater in group 2 than in group 1 (0.952 [SE 0.06] vs 0.739 [0

  19. Otimização de metodologia analítica para o doseamento de flavonoides de Bauhinia cheilantha (Bongard Steudel Optimization of analytic methodologies for quantifying flavonoids of Bauhinia cheilantha (Bongard Steudel

    Directory of Open Access Journals (Sweden)

    Tadeu José da Silva Peixoto Sobrinho

    2010-01-01

    Full Text Available The present study examined the optimization of stabilization and extraction processes of the flavonoids of Bauhinia cheilantha (Bongard Steudel. Four drying temperatures (room temperature, 40, 60 and 80 ºC and seven extraction systems (distilled water, 100% methanol, 80% methanol, 100% ethanol, 80% ethanol, 80% acetone and 60% acetone were examined. The results demonstrated a reduction in flavonoid levels with increasing drying temperatures; and 80% acetone, 80% ethanol, and methanol p.a extraction systems were found to be most efficient and its weren't differents statisticaly (p<0.05.

  20. 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

    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......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......-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...

  1. Flavonoids casticin and chrysosplenol D from Artemisia annua L. inhibit inflammation in vitro and in vivo

    Energy Technology Data Exchange (ETDEWEB)

    Li, Yu-Jie; Guo, Yan; Yang, Qing; Weng, Xiao-Gang; Yang, Lan; Wang, Ya-Jie; Chen, Ying; Zhang, Dong; Li, Qi; Liu, Xu-Cen; Kan, Xiao-Xi; Chen, Xi [Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700 (China); Zhu, Xiao-Xin, E-mail: zhuxx59@163.com [Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700 (China); Kmoníèková, Eva [Institute of Pharmacology and Toxicology, Faculty of Medicine in Pilsen, Charles University, Pilsen (Czech Republic); Zídek, Zdenìk [Institute of Experimental Medicine, Academy of Sciences of the Czech Republic, Vídeòská 1083, 142 20 Prague (Czech Republic)

    2015-08-01

    Background: The aim of our experiments was to investigate the anti-inflammatory properties of casticin and chrysosplenol D, two flavonoids present in Artemisia annua L. Methods: Topical inflammation was induced in ICR mice using croton oil. Mice were then treated with casticin or chrysosplenol D. Cutaneous histological changes and edema were assessed. ICR mice were intragastrically administrated with casticin or chrysosplenol D followed by intraperitoneal injection of lipopolysaccharide (LPS). Mouse Raw264.7 macrophage cells were incubated with casticin or chrysosplenol D. Intracellular phosphorylation was detected, and migration was assessed by trans-well assay. HT-29/NFκB-luc cells were incubated with casticin or chrysosplenol D in the presence or absence of LPS, and NF-κB activation was quantified. Results: In mice, administration of casticin (0.5, 1 and 1.5 μmol/cm{sup 2}) and chrysosplenol D (1 and 1.5 μmol/cm{sup 2}) inhibited croton oil-induced ear edema (casticin: 29.39–64.95%; chrysosplenol D: 37.76–65.89%, all P < 0.05) in a manner similar to indomethacin (0.5, 1 and 1.5 μmol/cm{sup 2}; 55.63–84.58%). Casticin (0.07, 0.13 and 0.27 mmol/kg) and chrysosplenol D (0.07, 0.14 and 0.28 mmol/kg) protected against LPS-induced systemic inflammatory response syndrome (SIRS) in mice (all P < 0.05), in a manner similar to dexamethasone (0.03 mmol/kg). Casticin and chrysosplenol D suppressed LPS-induced release of IL-1 beta, IL-6 and MCP-1, inhibited cell migration, and reduced LPS-induced IκB and c-JUN phosphorylation in Raw264.7 cells. JNK inhibitor SP600125 blocked the inhibitory effect of chrysosplenol D on cytokine release. Conclusions: The flavonoids casticin and chrysosplenol D from A. annua L. inhibited inflammation in vitro and in vivo. - Highlights: • We report a new activity of the flavonoids present in Artemisia annua L. • These flavonoids inhibit croton oil-induced ear edema in mice. • These flavonoids protect against LPS-induced SIRS in

  2. Dataset on the kinetics of the inhibition of PTP1B by the flavonoids and pheophytin A from Allophylus cominia

    Directory of Open Access Journals (Sweden)

    D.G. Semaan

    2018-04-01

    Full Text Available The data presented in this article are related to the research article under the title “in vitro anti-diabetic activity of flavonoids and pheophytins from Allophylus cominia Sw. on PTP1B, DPPIV, alpha-glucosidase and alpha-amylase enzymes” (Semaan et al., 2017 [3]. This article defines the kinetics of inhibition of flavonoids and pheophytin A extracts from A. cominia which showed an inhibition of the PTP1B enzyme activity. The main reason to make these results public is to confirm that this study was followed up and no more experiments are needed, also to confirm that these compounds can be reported as PTP1B inhibitors. Keywords: Flavonoids, Pheophytin, Inhibition, Kinetics, PTP1B enzyme

  3. Caenorhabditis elegans as Model System in Pharmacology and Toxicology: Effects of Flavonoids on Redox-Sensitive Signalling Pathways and Ageing

    Science.gov (United States)

    Koch, Karoline; Havermann, Susannah; Büchter, Christian

    2014-01-01

    Flavonoids are secondary plant compounds that mediate diverse biological activities, for example, by scavenging free radicals and modulating intracellular signalling pathways. It has been shown in various studies that distinct flavonoid compounds enhance stress resistance and even prolong the life span of organisms. In the last years the model organism C. elegans has gained increasing importance in pharmacological and toxicological sciences due to the availability of various genetically modified nematode strains, the simplicity of modulating genes by RNAi, and the relatively short life span. Several studies have been performed demonstrating that secondary plant compounds influence ageing, stress resistance, and distinct signalling pathways in the nematode. Here we present an overview of the modulating effects of different flavonoids on oxidative stress, redox-sensitive signalling pathways, and life span in C. elegans introducing the usability of this model system for pharmacological and toxicological research. PMID:24895670

  4. Caenorhabditis elegans as Model System in Pharmacology and Toxicology: Effects of Flavonoids on Redox-Sensitive Signalling Pathways and Ageing

    Directory of Open Access Journals (Sweden)

    Karoline Koch

    2014-01-01

    Full Text Available Flavonoids are secondary plant compounds that mediate diverse biological activities, for example, by scavenging free radicals and modulating intracellular signalling pathways. It has been shown in various studies that distinct flavonoid compounds enhance stress resistance and even prolong the life span of organisms. In the last years the model organism C. elegans has gained increasing importance in pharmacological and toxicological sciences due to the availability of various genetically modified nematode strains, the simplicity of modulating genes by RNAi, and the relatively short life span. Several studies have been performed demonstrating that secondary plant compounds influence ageing, stress resistance, and distinct signalling pathways in the nematode. Here we present an overview of the modulating effects of different flavonoids on oxidative stress, redox-sensitive signalling pathways, and life span in C. elegans introducing the usability of this model system for pharmacological and toxicological research.

  5. Dataset on the kinetics of the inhibition of PTP1B by the flavonoids and pheophytin A from Allophylus cominia.

    Science.gov (United States)

    Semaan, D G; Igoli, J O; Young, L; Marrero, E; Gray, A I; Rowan, E G

    2018-04-01

    The data presented in this article are related to the research article under the title "in vitro anti-diabetic activity of flavonoids and pheophytins from Allophylus cominia Sw. on PTP1B, DPPIV, alpha-glucosidase and alpha-amylase enzymes" (Semaan et al., 2017) [3]. This article defines the kinetics of inhibition of flavonoids and pheophytin A extracts from A. cominia which showed an inhibition of the PTP1B enzyme activity. The main reason to make these results public is to confirm that this study was followed up and no more experiments are needed, also to confirm that these compounds can be reported as PTP1B inhibitors.

  6. Quercetin - A Flavonoid Compound from Sarcopyramis bodinieri var ...

    African Journals Online (AJOL)

    The flavonoid compound was identified as quercetin by 1H-. NMR and ESI-MS ... phenolic compounds were isolated, and their .... scored under a fluorescence microscope (Carl. Zeiss .... Antioxidant Properties of Sarcopyramis bodinieri.

  7. 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.

  8. 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...

  9. 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 ...

  10. 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

  11. Extraction and Purification of Flavonoids from Radix Puerariae

    African Journals Online (AJOL)

    and preparations are now on sale. ... significant for optimization of extraction, resin selection and ... and flavonoids as indexes, optimize the proper density. ..... system. Sep Purif Technol. 2008; 62: 590-595. 12. Chen JH, Liau BC, Jong TT.

  12. 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)

  13. 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)

  14. 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

  15. Quantitative study of flavonoids in leaves of citrus plants.

    Science.gov (United States)

    Kawaii, S; Tomono, Y; Katase, E; Ogawa, K; Yano, M; Koizumi, M; Ito, C; Furukawa, H

    2000-09-01

    Leaf flavonoids were quantitatively determined in 68 representative or economically important Citrus species, cultivars, and near-Citrus relatives. Contents of 23 flavonoids including 6 polymethoxylated flavones were analyzed by means of reversed phase HPLC analysis. Principal component analysis revealed that the 7 associations according to Tanaka's classification were observed, but some do overlap each other. Group VII species could be divided into two different subgroups, namely, the first-10-species class and the last-19-species class according to Tanaka's classification numbers.

  16. Bioavailability, metabolism and potential health protective effects of dietary flavonoids

    DEFF Research Database (Denmark)

    Bredsdorff, Lea

    Dietary flavonoids constitute an important group of potential health protective compounds from fruits, vegetables, and plant-based products such as tea and wine. The beneficial effects of a diet high in flavonoids on the risk of coronary heart disease (CHD) have been shown in several epidemiologi......Dietary flavonoids constitute an important group of potential health protective compounds from fruits, vegetables, and plant-based products such as tea and wine. The beneficial effects of a diet high in flavonoids on the risk of coronary heart disease (CHD) have been shown in several...... of their content. In addition, variation in individual metabolic genotype and microflora may greatly affect the actual flavonoid exposure. The preventive effects of flavonoids on CHD are mainly ascribed to their anti-inflammatory and antioxidant activities. Several mechanisms of anti-inflammatory and antioxidant...... effective absorption of hesperetin and naringenin from the small intestine when consumed as glucosides compared to absorption in the colon VII after microbial degradation of the rhamnoglucosides. In addition it was shown that the conjugate profile was neither affected by the absorption site nor by a 3-fold...

  17. The biochemistry and medical significance of the flavonoids.

    Science.gov (United States)

    Havsteen, Bent H

    2002-01-01

    Flavonoids are plant pigments that are synthesised from phenylalanine, generally display marvelous colors known from flower petals, mostly emit brilliant fluorescence when they are excited by UV light, and are ubiquitous to green plant cells. The flavonoids are used by botanists for taxonomical classification. They regulate plant growth by inhibition of the exocytosis of the auxin indolyl acetic acid, as well as by induction of gene expression, and they influence other biological cells in numerous ways. Flavonoids inhibit or kill many bacterial strains, inhibit important viral enzymes, such as reverse transcriptase and protease, and destroy some pathogenic protozoans. Yet, their toxicity to animal cells is low. Flavonoids are major functional components of many herbal and insect preparations for medical use, e.g., propolis (bee's glue) and honey, which have been used since ancient times. The daily intake of flavonoids with normal food, especially fruit and vegetables, is 1-2 g. Modern authorised physicians are increasing their use of pure flavonoids to treat many important common diseases, due to their proven ability to inhibit specific enzymes, to simulate some hormones and neurotransmitters, and to scavenge free radicals.

  18. Flavonoids and phenolic acids from pearl millet (Pennisetum glaucum based foods and their functional implications

    Directory of Open Access Journals (Sweden)

    Vanisha S Nambiar

    2012-07-01

    Full Text Available Background: Pearl millet (Pennisetum glaucum, considered a poor man’s cereal, may be a repository of dietary antioxidants, especially flavonoids and phenolic acids, which provide bioactive mechanisms to reduce free radical induced oxidative stress and probably play a role in the prevention of ageing and various diseases associated with oxidative stress, such as cancer, cardiovascular, and neurodegenerative diseases.Objective: The present study focused on the identification of individual flavonoids and phenolic acids from seven commercial varieties of pearl millet and five samples of pearl millet-based traditional recipes of Banaskantha, Gujarat, India.Methods: Total phenols were determined by the Folin-Ciocalteu method, and individual polyphenol separation included the isolation and identification of (a flavonoids, (b phenolic acids, and (c glycoflavones involving interaction with diagnostic reagents and paper chromatographic separation of compounds and their UV-visible spectroscopic studies including hypsochromic and bathchromic shifts with reagents such as AlCl3, AlCl3/HCl, NaOMe, NaOAc,and NaOAc/H3PO3. Five traditional recipes consumed in the pearl millet producing belt of Banaskantha, Gujarat, India, were standardized in the laboratory and analyzed for phenol and individual flavonoids. Results: Total phenols in raw samples ranged from 268.5 - 420mg/100g of DW and 247.5 -Functional Foods in Health and Disease 2012, 2(7:251-264335mg/100g of DW in cooked recipes. The commonly identified flavonoids were tricin, acacetin, 3, 4 Di-OMe luteolin, and 4-OMe tricin. Five phenolic acids were identified: namely vanilic acid, syringic acid, melilotic acid, para-hydroxyl benzoic acid, and salicylic acid.Conclusion: The presence of flavonoids, such as tricin, acacetin, 3, 4 Di-OMe luteolin, and 4-OMe tricin, indicate the chemopreventive efficacy of pearl millet. They may be inversely related to mortality from coronary heart disease and to the incidence

  19. Extraction and identification of flavonoids from parsley extracts by HPLC analysis

    Science.gov (United States)

    Stan, M.; Soran, M. L.; Varodi, C.; Lung, I.

    2012-02-01

    Flavonoids are phenolic compounds isolated from a wide variety of plants, and are valuable for their multiple properties, including antioxidant and antimicrobial activities. In the present work, parsley (Petroselinum crispum L.) extracts were obtained by three different extraction techniques: maceration, ultrasonic-assisted and microwave-assisted solvent extractions. The extractions were performed with ethanol-water mixtures in various ratios. From these extracts, flavonoids like the flavones apigenin and luteolin, and the flavonols quercetin and kaempferol were identified using an HPLC Shimadzu apparatus equipped with PDA and MS detectors. The separation method involved a gradient step. The mobile phase consisted of two solvents: acetonitrile and distilled water with 0.1% formic acid. The separation was performed on a RP-C18 column.

  20. 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)

  1. Antioxidant Flavonoids from Nepeta floccosa Benth.

    Directory of Open Access Journals (Sweden)

    Liaqat Ali

    2015-06-01

    Full Text Available Antioxidants are the substances which significantly delay or prevent the development of age-related degenerative and chronic diseases caused by oxidative damage. Due to this, there is a considerable interest in the identification of lead molecules, which can inhibit the oxidation process or slow it down considerably. Based on the spectrofluorimetric analysis of superoxide and diphenylpicrylhydrazyl radical scavenging ability, the bio-assay guided isolation of methanolic extract of Nepeta floccosa Benth. was carried out. As a result of this study, one new flavanonol named nepetavanol (1 and four known flavonoids; dihydrokaempferol (2, naringenin (3, caulesnarinside (4, and poncirin (5 have been isolated. The structure of the new flavanonol was assigned on the basis of 1H- and 13C-NMR spectra including two-dimensional NMR techniques such as COSY, HMQC, and HMBC experiments and FABMS, EIMS, HR-MS data. Compound 1 , 2, and 3 showed significant activity whereas compounds 4 and 5 showed moderate activity against antioxidant assays.

  2. Flavonoid Regulation of HCN2 Channels*

    Science.gov (United States)

    Carlson, Anne E.; Rosenbaum, Joel C.; Brelidze, Tinatin I.; Klevit, Rachel E.; Zagotta, William N.

    2013-01-01

    The hyperpolarization-activated cyclic nucleotide-modulated (HCN) channels are pacemaker channels whose currents contribute to rhythmic activity in the heart and brain. HCN channels open in response to hyperpolarizing voltages, and the binding of cAMP to their cyclic nucleotide-binding domain (CNBD) facilitates channel opening. Here, we report that, like cAMP, the flavonoid fisetin potentiates HCN2 channel gating. Fisetin sped HCN2 activation and shifted the conductance-voltage relationship to more depolarizing potentials with a half-maximal effective concentration (EC50) of 1.8 μm. When applied together, fisetin and cAMP regulated HCN2 gating in a nonadditive fashion. Fisetin did not potentiate HCN2 channels lacking their CNBD, and two independent fluorescence-based binding assays reported that fisetin bound to the purified CNBD. These data suggest that the CNBD mediates the fisetin potentiation of HCN2 channels. Moreover, binding assays suggest that fisetin and cAMP partially compete for binding to the CNBD. NMR experiments demonstrated that fisetin binds within the cAMP-binding pocket, interacting with some of the same residues as cAMP. Together, these data indicate that fisetin is a partial agonist for HCN2 channels. PMID:24085296

  3. The biosynthetic origin of irregular monoterpenes in Lavandula: isolation and biochemical characterization of a novel cis-prenyl diphosphate synthase gene, lavandulyl diphosphate synthase.

    Science.gov (United States)

    Demissie, Zerihun A; Erland, Lauren A E; Rheault, Mark R; Mahmoud, Soheil S

    2013-03-01

    Lavender essential oils are constituted predominantly of regular monoterpenes, for example linalool, 1,8-cineole, and camphor. However, they also contain irregular monoterpenes including lavandulol and lavandulyl acetate. Although the majority of genes responsible for the production of regular monoterpenes in lavenders are now known, enzymes (including lavandulyl diphosphate synthase (LPPS)) catalyzing the biosynthesis of irregular monoterpenes in these plants have not been described. Here, we report the isolation and functional characterization of a novel cis-prenyl diphosphate synthase cDNA, termed Lavandula x intermedia lavandulyl diphosphate synthase (LiLPPS), through a homology-based cloning strategy. The LiLPPS ORF, encoding for a 305-amino acid long protein, was expressed in Escherichia coli, and the recombinant protein was purified by nickel-nitrilotriacetic acid affinity chromatography. The approximately 34.5-kDa bacterially produced protein specifically catalyzed the head-to-middle condensation of two dimethylallyl diphosphate units to LPP in vitro with apparent Km and kcat values of 208 ± 12 μm and 0.1 s(-1), respectively. LiLPPS is a homodimeric enzyme with a sigmoidal saturation curve and Hill coefficient of 2.7, suggesting a positive co-operative interaction among its catalytic sites. LiLPPS could be used to modulate the production of lavandulol and its derivatives in plants through metabolic engineering.

  4. Cloning and characterization of a glucosyltransferase from Crocus sativus stigmas involved in flavonoid glucosylation

    Directory of Open Access Journals (Sweden)

    Ahrazem Oussama

    2009-08-01

    Full Text Available Abstract Background Flavonol glucosides constitute the second group of secondary metabolites that accumulate in Crocus sativus stigmas. To date there are no reports of functionally characterized flavonoid glucosyltransferases in C. sativus, despite the importance of these compounds as antioxidant agents. Moreover, their bitter taste makes them excellent candidates for consideration as potential organoleptic agents of saffron spice, the dry stigmas of C. sativus. Results Using degenerate primers designed to match the plant secondary product glucosyltransferase (PSPG box we cloned a full length cDNA encoding CsGT45 from C. sativus stigmas. This protein showed homology with flavonoid glucosyltransferases. In vitro reactions showed that CsGT45 catalyses the transfer of glucose from UDP_glucose to kaempferol and quercetin. Kaempferol is the unique flavonol present in C. sativus stigmas and the levels of its glucosides changed during stigma development, and these changes, are correlated with the expression levels of CsGT45 during these developmental stages. Conclusion Findings presented here suggest that CsGT45 is an active enzyme that plays a role in the formation of flavonoid glucosides in C. sativus.

  5. Physiologically based kinetic modelling based prediction of oral systemic bioavailability of flavonoids, their metabolites, and their biological effects

    NARCIS (Netherlands)

    Boonpawa, Rungnapa

    2017-01-01

    Flavonoids, abundantly present in fruits and vegetables, have been reported to exert various positive health effects based on in vitro bioassays. However, effects detected in in vitro models cannot be directly correlated to human health as most in vitro studies have

  6. CYTOTOXICITY OF FLAVONOIDS AND SESQUITERPENE LACTONES FROM ARNICA SPECIES AGAINST THE GLC(4) AND THE COLO-320 CELL-LINES

    NARCIS (Netherlands)

    WOERDENBAG, HJ; MERFORT, [No Value; PASSREITER, CM; SCHMIDT, TJ; WILLUHN, G; VANUDEN, W; PRAS, N; KAMPINGA, HH; KONINGS, AWT

    1994-01-01

    The cytotoxicity of 21 flavonoids and 5 sesquiterpene lactones, as present in Arnica species, was studied in GLC(4), a human small cell lung carcinoma cell line, and in COLO 320, a human colorectal cancer cell line, using the microculture tetrazolium (MTT) assay. Following continuous incubation,

  7. Green tea extract only affects markers of oxidative status postprandially: lasting antioxidant effect of flavonoid-free diet

    DEFF Research Database (Denmark)

    Young, J.F.; Dragsted, Lars Ove; Haraldsdottir, J.

    2002-01-01

    Epidemiological studies suggest that foods rich in flavonoids might reduce the risk of cardiovascular disease and cancer. The objective of the present study was to investigate the effect of green tea extract (GTE) used as a food antioxidant on markers of oxidative status after dietary depletion...

  8. 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.

  9. Radioprotective effect of flavonoid quercetin on human lymphocytic cells

    International Nuclear Information System (INIS)

    Siqueira, Williams N.; Melo, Larissa S.A.; Lima, Maíra V.; Luna Filho, Ricardo L.C.; Melo, Ana M.M.A.; Silva, Edvane B.

    2017-01-01

    Several substances of synthetic and natural origin have been studied in relation to their ability to protect the body from damage caused by ionizing radiation. Among these substances, quercetin has been shown to be a molecule of natural origin with high radioprotective potential due to its antioxidant properties. The objective of this study was to determine, in vitro, the radioprotective effect of quercetin on human lymphocytes exposed to gamma radiation. Blood was irradiated at the 2.5, 3.5 and 4.5 Gy doses and then lymphocyte culture with quercetin at preselected concentrations of 37.5 and 75 μM. Subsequently, slides were prepared for analysis and quantification of the metaphases present in lymphocyte cells. The results demonstrated that irradiated lymphocytes and later exposed to quercetin presented a lower number of chromosomal alterations compared to the control group which was irradiated and not exposed to quercetin. Therefore, the results suggest a radioprotective effect of flavonoid quercetin on human lymphocytes exposed, in vitro, to ionizing radiation

  10. Flavonoids and Tannins from Smilax china L. Rhizome Induce Apoptosis Via Mitochondrial Pathway and MDM2-p53 Signaling in Human Lung Adenocarcinoma Cells.

    Science.gov (United States)

    Fu, San; Yang, Yanfang; Liu, Dan; Luo, Yan; Ye, Xiaochuan; Liu, Yanwen; Chen, Xin; Wang, Song; Wu, Hezhen; Wang, Yuhang; Hu, Qiwei; You, Pengtao

    2017-01-01

    In vitro evidence indicates that Smilax china L. rhizome (SCR) can inhibit cell proliferation. Therefore, in the present study, we analyzed the effects in vitro of SCR extracts on human lung adenocarcinoma A549 cells. Our results showed that A549 cell growth was inhibited in a dose- and time-dependent manner after treatment with SCR extracts. Total flavonoids and total tannins from SCR induced A549 apoptosis in a dose-dependent manner, as shown by our flow cytometry analysis, which was consistent with the alterations in nuclear morphology we observed. In addition, the total apoptotic rate induced by total tannins was higher than the rate induced by total flavonoids at the same dose. Cleaved-caspase-3 protein levels in A549 cells after treatment with total flavonoids or total tannins were increased in a dose-dependent manner, followed by the activation of caspase-8 and caspase-9, finally triggering to PARP cleavage. Furthermore, total flavonoids and total tannins increased the expression of Bax, decreased the expression of Bcl-2, and promoted cytochrome [Formula: see text] release. Moreover, MDM2 and p-MDM2 proteins were decreased, while p53 and p-p53 proteins were increased, both in a dose-dependent manner, after A549 treatment with total flavonoids and total tannins. Finally, cleaved-caspase-3 protein levels in the total flavonoids or total tannins-treated H1299 (p53 null) and p53-knockdown A549 cells were increased. Our results indicated that total flavonoids and total tannins from SCR exerted a remarkable effect in reducing A549 growth through their action on mitochondrial pathway and disruption of MDM2-p53 balance. Hence, our findings demonstrated a potential application of total flavonoids and total tannins from SCR in the treatment of human lung adenocarcinoma.

  11. Flavonoid metabolites reduce tumor necrosis factor-α secretion to a greater extent than their precursor compounds in human THP-1 monocytes.

    Science.gov (United States)

    di Gesso, Jessica L; Kerr, Jason S; Zhang, Qingzhi; Raheem, Saki; Yalamanchili, Sai Krishna; O'Hagan, David; Kay, Colin D; O'Connell, Maria A

    2015-06-01

    Flavonoids are generally studied in vitro, in isolation, and as unmetabolized precursor structures. However, in the habitual diet, multiple flavonoids are consumed together and found present in the circulation as complex mixtures of metabolites. Using a unique study design, we investigated the potential for singular or additive anti-inflammatory effects of flavonoid metabolites relative to their precursor structures. Six flavonoids, 14 flavonoid metabolites, and 29 combinations of flavonoids and their metabolites (0.1-10 μM) were screened for their ability to reduce LPS-induced tumor necrosis factor-α (TNF-α) secretion in THP-1 monocytes. One micromolar peonidin-3-glucoside, cyanidin-3-glucoside, and the metabolites isovanillic acid (IVA), IVA-glucuronide, vanillic acid-glucuronide, protocatechuic acid-3-sulfate, and benzoic acid-sulfate significantly reduced TNF-α secretion when in isolation, while there was no effect on TNF-α mRNA expression. Four combinations of metabolites that included 4-hydroxybenzoic acid (4HBA) and/or protocatechuic acid also significantly reduced TNF-α secretion to a greater extent than the precursors or metabolites alone. The effects on LPS-induced IL-1β and IL-10 secretion and mRNA expression were also examined. 4HBA significantly reduced IL-1β secretion but none of the flavonoids or metabolites significantly modified IL-10 secretion. This study provides novel evidence suggesting flavonoid bioactivity results from cumulative or additive effects of circulating metabolites. © 2015 The Authors. Molecular Nutrition & Food Research published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. Flavonoid metabolites reduce tumor necrosis factor‐α secretion to a greater extent than their precursor compounds in human THP‐1 monocytes

    Science.gov (United States)

    di Gesso, Jessica L.; Kerr, Jason S.; Zhang, Qingzhi; Raheem, Saki; Yalamanchili, Sai Krishna; O'Hagan, David; Kay, Colin D.; O'Connell, Maria A.

    2015-01-01

    1 Scope Flavonoids are generally studied in vitro, in isolation, and as unmetabolized precursor structures. However, in the habitual diet, multiple flavonoids are consumed together and found present in the circulation as complex mixtures of metabolites. Using a unique study design, we investigated the potential for singular or additive anti‐inflammatory effects of flavonoid metabolites relative to their precursor structures. 2 Methods and results Six flavonoids, 14 flavonoid metabolites, and 29 combinations of flavonoids and their metabolites (0.1–10 μM) were screened for their ability to reduce LPS‐induced tumor necrosis factor‐α (TNF‐α) secretion in THP‐1 monocytes. One micromolar peonidin‐3‐glucoside, cyanidin‐3‐glucoside, and the metabolites isovanillic acid (IVA), IVA‐glucuronide, vanillic acid‐glucuronide, protocatechuic acid‐3‐sulfate, and benzoic acid‐sulfate significantly reduced TNF‐α secretion when in isolation, while there was no effect on TNF‐α mRNA expression. Four combinations of metabolites that included 4‐hydroxybenzoic acid (4HBA) and/or protocatechuic acid also significantly reduced TNF‐α secretion to a greater extent than the precursors or metabolites alone. The effects on LPS‐induced IL‐1β and IL‐10 secretion and mRNA expression were also examined. 4HBA significantly reduced IL‐1β secretion but none of the flavonoids or metabolites significantly modified IL‐10 secretion. 3 Conclusion This study provides novel evidence suggesting flavonoid bioactivity results from cumulative or additive effects of circulating metabolites. PMID:25801720

  13. Optimizing Combinations of Flavonoids Deriving from Astragali Radix in Activating the Regulatory Element of Erythropoietin by a Feedback System Control Scheme

    Directory of Open Access Journals (Sweden)

    Hui Yu

    2013-01-01

    Full Text Available Identifying potent drug combination from a herbal mixture is usually quite challenging, due to a large number of possible trials. Using an engineering approach of the feedback system control (FSC scheme, we identified the potential best combinations of four flavonoids, including formononetin, ononin, calycosin, and calycosin-7-O-β-D-glucoside deriving from Astragali Radix (AR; Huangqi, which provided the best biological action at minimal doses. Out of more than one thousand possible combinations, only tens of trials were required to optimize the flavonoid combinations that stimulated a maximal transcriptional activity of hypoxia response element (HRE, a critical regulator for erythropoietin (EPO transcription, in cultured human embryonic kidney fibroblast (HEK293T. By using FSC scheme, 90% of the work and time can be saved, and the optimized flavonoid combinations increased the HRE mediated transcriptional activity by ~3-fold as compared with individual flavonoid, while the amount of flavonoids was reduced by ~10-fold. Our study suggests that the optimized combination of flavonoids may have strong effect in activating the regulatory element of erythropoietin at very low dosage, which may be used as new source of natural hematopoietic agent. The present work also indicates that the FSC scheme is able to serve as an efficient and model-free approach to optimize the drug combination of different ingredients within a herbal decoction.

  14. Lettuce flavonoids screening and phenotyping by chlorophyll fluorescence excitation ratio.

    Science.gov (United States)

    Zivcak, Marek; Brückova, Klaudia; Sytar, Oksana; Brestic, Marian; Olsovska, Katarina; Allakhverdiev, Suleyman I

    2017-06-01

    Environmentally induced variation and the genotypic differences in flavonoid and phenolic content in lettuce can be reliably detected using the appropriate parameters derived from the records of rapid non-invasive fluorescence technique. The chlorophyll fluorescence excitation ratio method was designed as a rapid and non-invasive tool to estimate the content of UV-absorbing phenolic compounds in plants. Using this technique, we have assessed the dynamics of accumulation of flavonoids related to developmental changes and environmental effects. Moreover, we have tested appropriateness of the method to identify the genotypic differences and fluctuations in total phenolics and flavonoid content in lettuce. Six green and two red genotypes of lettuce (Lactuca sativa L.) grown in pots were exposed to two different environments for 50 days: direct sunlight (UV-exposed) and greenhouse conditions (low UV). The indices based on the measurements of chlorophyll fluorescence after red, green and UV excitation indicated increase of the content of UV-absorbing compounds and anthocyanins in the epidermis of lettuce leaves. In similar, the biochemical analyses performed at the end of the experiment confirmed significantly higher total phenolic and flavonoid content in lettuce plants exposed to direct sun compared to greenhouse conditions and in red compared to green genotypes. As the correlation between the standard fluorescence indices and the biochemical records was negatively influenced by the presence of red genotypes, we proposed the use of a new parameter named Modified Flavonoid Index (MFI) taking into an account both absorbance changes due to flavonol and anthocyanin content, for which the correlation with flavonoid and phenolic content was relatively good. Thus, our results confirmed that the fluorescence excitation ratio method is useful for identifying the major differences in phenolic and flavonoid content in lettuce plants and it can be used for high-throughput pre

  15. Comparative Analysis of the Interaction between Different Flavonoids and PDIA3

    Science.gov (United States)

    Giamogante, Flavia; Marrocco, Ilaria; Romaniello, Donatella; Eufemi, Margherita; Chichiarelli, Silvia

    2016-01-01

    Flavonoids, plant secondary metabolites present in fruits, vegetables, and products such as tea and red wine, show antioxidant, anti-inflammatory, antithrombotic, antiviral, and antitumor activity. PDIA3 is a member of the protein disulfide isomerase family mainly involved in the correct folding of newly synthetized glycoproteins. PDIA3 is associated with different human pathologies such as cancer, prion disorders, Alzheimer's disease, and Parkinson's diseases and it has the potential to be a pharmacological target. The interaction of different flavonoids with PDIA3 was investigated by quenching fluorescence analysis and the effects on protein activity were evaluated. A higher affinity was observed for eupatorin-5-methyl ether and eupatorin which also inhibit reductase activity of PDIA3 but do not significantly affect its DNA binding activity. The use of several flavonoids differing in chemical structure and functional groups allows us to make some consideration about the relationship between ligand structure and the affinity for PDIA3. The specific flavone backbone conformation and the degree of polarity seem to play an important role for the interaction with PDIA3. The binding site is probably similar but not equivalent to that of green tea catechins, which, as previously demonstrated, can bind to PDIA3 and prevent its interaction with DNA. PMID:28044092

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

    Directory of Open Access Journals (Sweden)

    Ehsan Oskoueian

    2011-05-01

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

  17. CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells

    International Nuclear Information System (INIS)

    Androutsopoulos, Vasilis P.; Ruparelia, Ketan; Arroo, Randolph R.J.; Tsatsakis, Aristidis M.; Spandidos, Demetrios A.

    2009-01-01

    Among the different mechanisms proposed to explain the cancer-protecting effect of dietary flavonoids, substrate-like interactions with cytochrome P450 CYP1 enzymes have recently been explored. In the present study, the metabolism of the flavonoids chrysin, baicalein, scutellarein, sinensetin and genkwanin by recombinant CYP1A1, CYP1B1 and CYP1A2 enzymes, as well as their antiproliferative activity in MDA-MB-468 human breast adenocarcinoma and MCF-10A normal breast cell lines, were investigated. Baicalein and 6-hydroxyluteolin were the only conversion products of chrysin and scutellarein metabolism by CYP1 family enzymes, respectively, while baicalein itself was not metabolized further. Sinensetin and genkwanin produced a greater number of metabolites and were shown to inhibit strongly in vitro proliferation of MDA-MB-468 cells at submicromolar and micromolar concentrations, respectively, without essentially affecting the viability of MCF-10A cells. Cotreatment of the CYP1 family inhibitor acacetin reversed the antiproliferative activity noticed for the two flavones in MDA-MB-468 cells to 13 and 14 μM respectively. In contrast chrysin, baicalein and scutellarein inhibited proliferation of MDA-MB-468 cells to a lesser extent than sinensetin and genkwanin. The metabolism of genkwanin to apigenin and of chrysin to baicalein was favored by CYP1B1 and CYP1A1, respectively. Taken together the data suggests that CYP1 family enzymes enhance the antiproliferative activity of dietary flavonoids in breast cancer cells, through bioconversion to more active products.

  18. Reaction of Acetaldehyde with Wine Flavonoids in the Presence of Sulfur Dioxide.

    Science.gov (United States)

    Sheridan, Marlena K; Elias, Ryan J

    2016-11-16

    Acetaldehyde is responsible for many of the beneficial changes that occur in red wine as a result of oxidation. Ethylidene bridges are formed between flavonoids upon their reaction with acetaldehyde, which can contribute to improvements in color stability and SO 2 -resistant pigments. In the present study, the reactions between acetaldehyde and various flavonoids (catechin, tannins from grape seed extract, and malvidin-3-glucoside) were examined in a model wine system. Lower pH conditions were seen to significantly increase the rate of reaction with acetaldehyde, whereas dissolved oxygen did not affect the rate. In systems containing SO 2 , the rate of reaction of acetaldehyde with catechin was slowed but was not prevented until SO 2 was in great excess. Significant improvements in color stability were also observed after treatment with acetaldehyde, despite the presence of equimolar SO 2 . These results demonstrate that acetaldehyde is reactive in its sulfonate form, which is contrary to widely held assumptions. In addition, the products of the reaction of flavonoids with acetaldehyde were characterized using MALDI-TOF MS in this study. Ethyl-bridged catechin nonamers were observed, as well as anthocyanin and pyranoanthocyanin derivatives of catechin and tannin oligomers. The results of this work illustrate the significance of acetaldehyde reactions in forming stable pigments in wine and the reactivity of acetaldehyde from its sulfonate form.

  19. Comparative Analysis of the Interaction between Different Flavonoids and PDIA3

    Directory of Open Access Journals (Sweden)

    Flavia Giamogante

    2016-01-01

    Full Text Available Flavonoids, plant secondary metabolites present in fruits, vegetables, and products such as tea and red wine, show antioxidant, anti-inflammatory, antithrombotic, antiviral, and antitumor activity. PDIA3 is a member of the protein disulfide isomerase family mainly involved in the correct folding of newly synthetized glycoproteins. PDIA3 is associated with different human pathologies such as cancer, prion disorders, Alzheimer’s disease, and Parkinson’s diseases and it has the potential to be a pharmacological target. The interaction of different flavonoids with PDIA3 was investigated by quenching fluorescence analysis and the effects on protein activity were evaluated. A higher affinity was observed for eupatorin-5-methyl ether and eupatorin which also inhibit reductase activity of PDIA3 but do not significantly affect its DNA binding activity. The use of several flavonoids differing in chemical structure and functional groups allows us to make some consideration about the relationship between ligand structure and the affinity for PDIA3. The specific flavone backbone conformation and the degree of polarity seem to play an important role for the interaction with PDIA3. The binding site is probably similar but not equivalent to that of green tea catechins, which, as previously demonstrated, can bind to PDIA3 and prevent its interaction with DNA.

  20. In Silico Investigation of Flavonoids as Potential Trypanosomal Nucleoside Hydrolase Inhibitors

    Directory of Open Access Journals (Sweden)

    Christina Hung Hung Ha

    2015-01-01

    Full Text Available Human African Trypanosomiasis is endemic to 37 countries of sub-Saharan Africa. It is caused by two related species of Trypanosoma brucei. Current therapies suffer from resistance and public accessibility of expensive medicines. Finding safer and effective therapies of natural origin is being extensively explored worldwide. Pentamidine is the only available therapy for inhibiting the P2 adenosine transporter involved in the purine salvage pathway of the trypanosomatids. The objective of the present study is to use computational studies for the investigation of the probable trypanocidal mechanism of flavonoids. Docking experiments were carried out on eight flavonoids of varying level of hydroxylation, namely, flavone, 5-hydroxyflavone, 7-hydroxyflavone, chrysin, apigenin, kaempferol, fisetin, and quercetin. Using AutoDock 4.2, these compounds were tested for their affinity towards inosine-adenosine-guanosine nucleoside hydrolase and the inosine-guanosine nucleoside hydrolase, the major enzymes of the purine salvage pathway. Our results showed that all of the eight tested flavonoids showed high affinities for both hydrolases (lowest free binding energy ranging from −10.23 to −7.14 kcal/mol. These compounds, especially the hydroxylated derivatives, could be further studied as potential inhibitors of the nucleoside hydrolases.

  1. Flavonoids Promote Haustoria Formation in the Root Parasite Triphysaria versicolor1

    Science.gov (United States)

    Albrecht, Huguette; Yoder, John I.; Phillips, Donald A.

    1999-01-01

    Parasitic plants in the Scrophulariaceae develop infective root structures called haustoria in response to chemical signals released from host-plant roots. This study used a simple in vitro assay to characterize natural and synthetic molecules that induce haustoria in the facultative parasite Triphysaria versicolor. Several phenolic acids, flavonoids, and the quinone 2,6-dimethoxy-p-benzoquinone induced haustoria in T. versicolor root tips within hours after treatment. The concentration at which different molecules were active varied widely, the most active being 2,6-dimethoxy-p-benzoquinone and the anthocyanidin peonidin. Maize (Zea mays) seeds are rich sources of molecules that induce T. versicolor haustoria in vitro, and chromatographic analyses indicated that the active molecules present in maize-seed rinses include anthocyanins, other flavonoids, and simple phenolics. The presence of different classes of inducing molecules in seed rinses was substantiated by the observation that maize kernels deficient in chalcone synthase, a key enzyme in flavonoid biosynthesis, released haustoria-inducing molecules, although at reduced levels compared with wild-type kernels. We discuss these results in light of existing models for host perception in the related parasitic plant Striga. PMID:9952454

  2. Flavonoids from Piper delineatum modulate quorum-sensing-regulated phenotypes in Vibrio harveyi.

    Science.gov (United States)

    Martín-Rodríguez, Alberto J; Ticona, Juan C; Jiménez, Ignacio A; Flores, Ninoska; Fernández, José J; Bazzocchi, Isabel L

    2015-09-01

    Quorum sensing (QS), or bacterial cell-to-cell communication, is a key process for bacterial colonization of substrata through biofilm formation, infections, and production of virulence factors. In an ongoing investigation of bioactive secondary metabolites from Piper species, four new flavonoids (1-4), along with five known ones (5-9) were isolated from the leaves of Piper delineatum. Their stereostructures were established by spectroscopic and spectrometric methods, including 1D and 2D NMR experiments, and comparison with data reported in the literature. The compounds were screened for their ability to interfere with QS signaling in the bacterial model Vibrio harveyi. Four compounds from this series (2, 3, 6, and 7) exhibited remarkable activity in the micromolar range, being compounds 3 and 7 particularly attractive since they did not affect bacterial growth. The results suggest that these flavonoids disrupt QS-mediated bioluminescence by interaction with elements downstream LuxO in the QS circuit of V. harveyi, and also, they exhibited a strong dose-dependent inhibition of biofilm formation. The present findings shed light on the QS inhibition mechanisms of flavonoids, underlining their potential applications. Copyright © 2015 Elsevier Ltd. All rights reserved.

  3. Flavonoids as matrices for MALDI-TOF mass spectrometric analysis of transition metal complexes

    Science.gov (United States)

    Petkovic, Marijana; Petrovic, Biljana; Savic, Jasmina; Bugarcic, Zivadin D.; Dimitric-Markovic, Jasmina; Momic, Tatjana; Vasic, Vesna

    2010-02-01

    Matrix-assisted laser desorption and ionization time-of-flight mass spectrometry (MALDI-TOF MS) is a suitable method for the analysis of inorganic and organic compounds and biomolecules. This makes MALDI-TOF MS convenient for monitoring the interaction of metallo-drugs with biomolecules. Results presented in this manuscript demonstrate that flavonoids such as apigenin, kaempferol and luteolin are suitable for MALDI-TOF MS analysis of Pt(II), Pd(II), Pt(IV) and Ru(III) complexes, giving different signal-to-noise ratios of the analyte peak. The MALDI-TOF mass spectra of inorganic complexes acquired with these flavonoid matrices are easy to interpret and have some advantages over the application of other commonly used matrices: a low number of matrix peaks are detectable and the coordinative metal-ligand bond is, in most cases, preserved. On the other hand, flavonoids do not act as typical matrices, as their excess is not required for the acquisition of MALDI-TOF mass spectra of inorganic complexes.

  4. 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.

  5. Protective Effects of Flavonoid Pomiferin on Heart Ischemia-Reperfusion

    Directory of Open Access Journals (Sweden)

    J. Nečas

    2007-01-01

    Full Text Available The objective of the present 15-day study was to evaluate the cardioprotective potential of flavonoid pomiferin isolated from the infructences of Maclura pomifera, Moraceae, against ischemia-reperfusion induced injury in rat hearts as a model of antioxidant-based composite therapy. Studies were performed with isolated, modifi ed Langendorff-perfused rat hearts and ischemia of heart was initiated by stopping the coronary flow for 30 min, followed by 60 min of reperfusion (14 ml min-1. Wistar rats were divided into three groups. The treated group received pomiferin (5 mg/kg/day in 0.5% Avicel; the placebo group received only 0.5% Avicel; the intact group was left without any applications. Biochemical indicators of oxidative damage, lipid peroxidation product malondialdehyde, antioxidant enzymes (superoxide dismutase, glutathione peroxidase, total antioxidant activity in serum and myocardium has been evaluated. We also examined the effect of pomiferin on cardiac function (left ventricular end-diastolic pressure, left ventricular pressure, peak positive +dP/dt (rate of pressure development after ischemia and reperfusion. Our results demonstrate that pomiferin attenuates the myocardial dysfunction provoked by ischemiareperfusion. This was confirmed by the increase in both the antioxidant enzyme values and the total antioxidant activity. The cardio-protection provided by pomiferin treatment results from the suppression of oxidative stress and correlates with the improved ventricular function.

  6. Exploring the molecular targets of dietary flavonoid fisetin in cancer.

    Science.gov (United States)

    Syed, Deeba N; Adhami, Vaqar Mustafa; Khan, Naghma; Khan, Mohammad Imran; Mukhtar, Hasan

    2016-10-01

    The last few decades have seen a resurgence of interest among the scientific community in exploring the efficacy of natural compounds against various human cancers. Compounds of plant origin belonging to different groups such as alkaloids, flavonoids and polyphenols evaluated for their cancer preventive effects have yielded promising data, thereby offering a potential therapeutic alternative against this deadly disease. The flavonol fisetin (3,3',4',7-tetrahydroxyflavone), present in fruits and vegetables such as strawberries, apple, cucumber, persimmon, grape and onion, was shown to possess anti-microbial, anti-inflammatory, anti-oxidant and more significantly anti-carcinogenic activity when assessed in diverse cell culture and animal model systems. The purpose of this review is to update and discuss key findings obtained till date from in vitro and in vivo studies on fisetin, with special focus on its anti-cancer role. The molecular mechanism(s) described in the observed growth inhibitory effects of fisetin in different cancer cell types is also summarized. Moreover, an attempt is made to delineate the direction of future studies that could lead to the development of fisetin as a potent chemopreventive/chemotherapeutic agent against cancer. Copyright © 2016 Elsevier Ltd. All rights reserved.

  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. 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.

  9. 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.

  10. 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.

  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.

    2017-01-01

    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

  12. Radioprotective effects of antioxidative plant flavonoids in mice

    International Nuclear Information System (INIS)

    Shimoi, Kayoko; Masuda, Shuichi; Shen, Bingrong; Furugori, Michiyo; Kinae, Naohide

    1996-01-01

    Radioprotective effects of tea infusions and plant flavonoids were investigated by using the micronucleus test for anticlastogenic activity and the thiobarbituric acid assay for antioxidative activity. A single gastric intubation of rooibos tea (Aspalathus linearis) infusion at 1 ml per mouse 2 h prior to γ-ray irradiation (1.5 Gy) reduced the frequency of micronucleated reticulocytes (MNRETs). After the fractionation of rooibos tea infusion, the flavonoid fraction was found to be most anticlastogenic and antioxidative. From this fraction, luteolin was isolated as an effective component. Then, anticlastogenic effects of 12 flavonoids containing luteolin and their antioxidative activities against lipid peroxidation by Fenton's reagent were examined. A good correlation (r=0.717) was observed between both activities. Luteolin showed the most effective potency. A gastric intubation of luteolin (10 μmol/kg) 2 h prior to γ-ray irradiation (6 Gy) suppressed lipid peroxidation in mouse bone marrow and spleen and a trend of protective effect of luteolin against the decrease of endogenous ascorbic acid in mouse bone marrow after γ-ray irradiation (3 Gy) was observed. These results suggest that plant flavonoids, which show antioxidative potency in vitro, work as antioxidants in vivo and their radioprotective effects may be attributed to their scavenging potency towards free radicals such as hydroxyl radicals. Therefore, the flavonoids contained in tea, vegetables and fruits seem to be important as antioxidants in the human diet

  13. 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

  14. 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.

  15. 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

  16. Mobilization of Copper ions by Flavonoids in Human Peripheral Lymphocytes Leads to Oxidative DNA Breakage: A Structure Activity Study

    Science.gov (United States)

    Arif, Hussain; Rehmani, Nida; Farhan, Mohd; Ahmad, Aamir; Hadi, Sheikh Mumtaz

    2015-01-01

    Epidemiological studies have linked dietary consumption of plant polyphenols with lower incidence of various cancers. In particular, flavonoids (present in onion, tomato and other plant sources) induce apoptosis and cytotoxicity in cancer cells. These can therefore be used as lead compounds for the synthesis of novel anticancer drugs with greater bioavailability. In the present study, we examined the chemical basis of cytotoxicity of flavonoids by studying the structure–activity relationship of myricetin (MN), fisetin (FN), quercetin (QN), kaempferol (KL) and galangin (GN). Using single cell alkaline gel electrophoresis (comet assay), we established the relative efficiency of cellular DNA breakage as MN > FN > QN > KL > GN. Also, we determined that the cellular DNA breakage was the result of mobilization of chromatin-bound copper ions and the generation of reactive oxygen species. The relative DNA binding affinity order was further confirmed using molecular docking and thermodynamic studies through the interaction of flavonoids with calf thymus DNA. Our results suggest that novel anti-cancer molecules should have ortho-dihydroxy groups in B-ring and hydroxyl groups at positions 3 and 5 in the A-ring system. Additional hydroxyl groups at other positions further enhance the cellular cytotoxicity of the flavonoids. PMID:26569217

  17. Mobilization of Copper ions by Flavonoids in Human Peripheral Lymphocytes Leads to Oxidative DNA Breakage: A Structure Activity Study

    Directory of Open Access Journals (Sweden)

    Hussain Arif

    2015-11-01

    Full Text Available Epidemiological studies have linked dietary consumption of plant polyphenols with lower incidence of various cancers. In particular, flavonoids (present in onion, tomato and other plant sources induce apoptosis and cytotoxicity in cancer cells. These can therefore be used as lead compounds for the synthesis of novel anticancer drugs with greater bioavailability. In the present study, we examined the chemical basis of cytotoxicity of flavonoids by studying the structure–activity relationship of myricetin (MN, fisetin (FN, quercetin (QN, kaempferol (KL and galangin (GN. Using single cell alkaline gel electrophoresis (comet assay, we established the relative efficiency of cellular DNA breakage as MN > FN > QN > KL > GN. Also, we determined that the cellular DNA breakage was the result of mobilization of chromatin-bound copper ions and the generation of reactive oxygen species. The relative DNA binding affinity order was further confirmed using molecular docking and thermodynamic studies through the interaction of flavonoids with calf thymus DNA. Our results suggest that novel anti-cancer molecules should have ortho-dihydroxy groups in B-ring and hydroxyl groups at positions 3 and 5 in the A-ring system. Additional hydroxyl groups at other positions further enhance the cellular cytotoxicity of the flavonoids.

  18. 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.

  19. 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.

  20. 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.

  1. 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)

  2. 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.

  3. 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)

  4. In vitro biotransformation of flavonoids by rat liver microsomes

    DEFF Research Database (Denmark)

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

    1998-01-01

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

  5. Novel Investigations of Flavonoids as Chemopreventive Agents for Hepatocellular Carcinoma

    Directory of Open Access Journals (Sweden)

    Chen-Yi Liao

    2015-01-01

    Full Text Available We would like to highlight the application of natural products to hepatocellular carcinoma (HCC. We will focus on the natural products known as flavonoids, which target this disease at different stages of hepatocarcinogenesis. In spite of the use of chemotherapy and radiotherapy in treating HCC, patients with HCC still face poor prognosis because of the nature of multidrug resistance and toxicity derived from chemotherapy and radiotherapy. Flavonoids can be found in many vegetables, fruits, and herbal medicines that exert their different anticancer effects via different intracellular signaling pathways and serve as antioxidants. In this review, we will discuss seven common flavonoids that exert different biological effects against HCC via different pathways.

  6. Dietary PUFA and flavonoids as deterrents for environmental pollutants.

    Science.gov (United States)

    Watkins, Bruce A; Hannon, Kevin; Ferruzzi, Mario; Li, Yong

    2007-03-01

    Various nutrients and plant-derived phytochemicals are associated with a reduced risk of many diet-related chronic diseases including cardiovascular disease, cancer, diabetes, arthritis and osteoporosis. A common theme that links many chronic diseases is uncontrolled inflammation. The long-chain (LC) omega-3 polyunsaturated fatty acids (PUFA) and flavonoids are known to possess anti-inflammatory actions in cell cultures, animal models and humans. Minimizing the condition of persistent inflammation has been a primary aim for drug development, but understanding how food components attenuate this process is at the nexus for improving the human condition. The prevalence of environmental toxins such as heavy metals and organics that contribute to diminished levels of antioxidants likely aggravates inflammatory states when intakes of omega-3 PUFA and flavonoids are marginal. Scientists at Purdue University have formed a collaboration to better understand the metabolism and physiology of flavonoids. This new effort is focused on determining how candidate flavonoids and their metabolites affect gene targets of inflammation in cell culture and animal models. The challenge of this research is to understand how LC omega-3 PUFA and flavonoids affect the biology of inflammation. The goal is to determine how nutrients and phytochemicals attenuate chronic inflammation associated with a number of diet-related diseases that occur throughout the life cycle. The experimental approach involves molecular, biochemical and physiological endpoints of aging, cancer, obesity and musculoskeletal diseases. Examples include investigations on the combined effects of PUFA and cyanidins on inflammatory markers in cultures of human cancer cells. The actions of catechins and PUFA on muscle loss and osteopenia are being studied in a rodent model of disuse atrophy to explain how muscle and bone communicate to prevent tissue loss associated with injury, disease and aging. The purpose of this review is

  7. Ultraviolet light inhibition of phytochrome-induced flavonoid biosynthesis and DNA photolyase formation in mustard cotyledons (Sinapis alba L.)

    International Nuclear Information System (INIS)

    Buchholz, G.; Ehmann, B.; Wellmann, E.

    1995-01-01

    In cotyledons of etiolated mustard (Sinapis alba L.) seedlings, phytochrome-far-red-absorbing form-induced flavonoid biosynthesis was found to be inhibited by short-term ultraviolet (UV) irradiations. UV inhibition was shown for the synthesis of quercetin, anthocyanin, and also for the accumulation of the mRNA for chalcone synthase, the key enzyme of this pathway. The UV effect was more pronounced on flavonoid biosynthesis, a process that selectively occurs in the epidermal layers, than on the synthesis of mRNA for chlorophyll a/b-binding protein localized in the mesophyll tissue. These UV inhibitory effects were accompanied by cyclobutane pyrimidine dimer (CPD) formation showing a linear fluence-response relationship. CPD formation and UV inhibition of flavonoid biosynthesis was found to be partially reversible by blue/UV-A light via DNA photolyase (PRE), allowing photoreactivation of the DNA by splitting of CPDs, which are the cause of the UV effect. Like flavonoid formation PRE was also induced by the far-red-absorbing form of phytochrome and induction was inhibited by UV. A potential risk of inhibition, in response to solar UV-B irradiation, was shown for anthocyanin formation. This inhibition, however, occurred only if photoreactivation was experimentally reduced. The PRE activity present in the etiolated seedlings (further increasing about 5-fold during light acclimatization) appears to be sufficient to prevent the persistence of CPDs even under conditions of high solar irradiation

  8. Determination of Flavonoids and Anthocyanins in Nitraria tangutorum by High Performance Liquid Chromatography Coupled with Tandem Mass Spectrometry.

    Science.gov (United States)

    Zhe, Gao; Ying-Chun, Wang; Yan-Xu, Chang

    2016-01-01

    Using high-performance liquid chromatography coupled with diode array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-MSn) method, qualitative and quantitative analysis of flavonoids of stems, leaves, fruits and seeds, and anthocyanidin of fresh fruits in Nitraria tangutorum were performed. A total of 14 flavonoid components were identified from the seeds of N. tangutorum including three quercetin derivatives, three kaempferol derivatives, and eight isorhamnetin derivatives. A total of 12, 10, and 7 flavonoid components were identified from leaves, stems, and fruits of N. tangutorum, respectively; all were present in seeds also. The total content of flavonoids in leaves was the highest, up to 42.43 mg/g·dry weight. A total of 12 anthocyanidin components were identified from the fresh fruits of N. tangutorum, belonging to five anthocyanidin. The total content of anthocyanidin in fresh fruits was up to 45.83 mg/100 g· fresh weight, of which the acylated anthocyanidin accounted for 65.7%. The HPLC-DAD-MS(n) method can be operated easily, rapidly, and accurately, and is feasible for qualitative and quantitative analysis of flavone glycosides in N. tangutorum.

  9. Flavonoids Isolated From the Flowers of Limonium bicolor and their In vitro Antitumor Evaluation.

    Science.gov (United States)

    Chen, Jian; Teng, Jiehui; Ma, Li; Tong, Haiying; Ren, Bingru; Wang, Linshan; Li, Weilin

    2017-01-01

    Limonium bicolor , a halophytic species, can grow in saline or saline-alkali soil, is well known as a traditional Chinese medicine. Recently it attracted much attention for its treatment for cancer. The present study was performed to evaluate this species from the phytochemical standpoint and the possible relationship between the antitumor activity and its natural products. The chemical constituents from the flowers of L. bicolor were investigated through bioassay-guided fractionation and isolation. All the individual compounds were characterized by spectroscopic analysis and their potential antitumor activity was tested against three different human tumor cell lines by MTT assays. The EtOAc extract was proven as the most potent fraction and further fractionation led to the isolation of 15 natural flavonoids, which were characterized as luteolin (1), acacetin (2), quercetin (3), isorhamnetin (4), kaempferol (5), eriodictyol (6), kaempferol-3-O-α-L-rhamnoside (7), kaempferol-3-O-β-D-glucoside (8), quercetin-3-O-α-L-rhamnoside (9), quercetin-3-O-β-D-glucoside (10), quercetin-3-O-β-D-galactoside (11), myricetin-3-O-α-L-rhamnoside (12), kaempferol-3-O-(6″-O-galloyl)-β-D-glucoside (13), hesperidin (14) and rutin (15). The biotesting results demonstrated that both compounds 1 and 3 showed good cytotoxicity against human colon cancer cells (LOVO). Compound 5 exhibited relative greater growth inhibition against both human breast cancer cells (MCF-7) and osteosarcoma cell lines (U2-OS) at the concentration of 100 μg/mL. On the basis of these findings, the flavonoids were deduced to be potentially responsible for the antitumor activity of L. bicolor . The preliminary structure-activity relationship analysis suggests that the 3-O-glycosylation moiety in natural flavonoids was not essential for the antiproliferative activity on LOVO and U2-OS cells. The phytochemical investigation of Limonium bicolor led to the isolation of 15 flavonoids.The biotesting of the

  10. 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)

  11. Dietary flavonoid intake at midlife and healthy aging in women.

    Science.gov (United States)

    Samieri, Cécilia; Sun, Qi; Townsend, Mary K; Rimm, Eric B; Grodstein, Francine

    2014-12-01

    Dietary flavonoids have been related to lower risks of various chronic diseases, but it is unclear whether flavonoid intake in midlife helps to maintain good health and wellbeing in aging. We examined the relation of flavonoid intake in midlife with the prevalence of healthy aging. We included 13,818 women from the Nurses' Health Study with dietary data and no major chronic diseases in 1984-1986 when they were aged in their late 50s (median age: 59 y); all women provided information on multiple aspects of aging an average of 15 y later. Intakes of 6 major flavonoid subclasses in midlife were ascertained on the basis of averaged intakes of flavonoid-rich foods from 2 food-frequency questionnaires (1984-1986). We defined healthy compared with usual aging as of age 70 y; healthy aging was based on survival to ≥70 y with maintenance of 4 health domains (no major chronic diseases or major impairments in cognitive or physical function or mental health). Of women who survived until ≥70 y of age, 1517 women (11.0%) met our criteria for healthy aging. Compared with women in the lowest quintile of intake, women in the highest quintile of intake of several flavonoid subclasses at midlife had greater odds of healthy aging. After multivariable adjustment, ORs were as follows: flavones, 1.32 (95% CI: 1.10, 1.58); flavanone, 1.28 (95% CI: 1.08, 1.53); anthocyanin, 1.25 (95% CI: 1.04, 1.50); and flavonol, 1.18 (95% CI: 0.98, 1.42) (all P-trend ≤ 0.02). Consistently, greater intakes of major sources of these flavonoids (i.e., oranges, berries, onions, and apples) were associated with increased odds of healthy aging. We showed no association with flavan-3-ol monomers (P-trend = 0.80) or polymers (P-trend = 0.63). Higher intake of flavonoids at midlife, specifically flavones, flavanones, anthocyanins, and flavonols, is associated with greater likelihood of health and wellbeing in individuals surviving to older ages. © 2014 American Society for Nutrition.

  12. Triterpenes and flavonoids from the roots of Mauritia flexuosa

    Directory of Open Access Journals (Sweden)

    Hector H. F. Koolen

    2011-11-01

    Full Text Available Mauritia flexuosa L. f., Arecaceae, is an endemic species of South America. This species was studied with the intent to isolate the constituents of its roots. After the fractionation of the n-hexane and methanolic extracts from the roots of M. flexuosa, six triterpenes were obtained: friedelin, taraxerone, lupenyl acetate, lupenone, betulin and betulinic acid, along with three flavonoids: rutin, quercitrin and quercetin. All the compounds were identified by analysis of NMR and MS data and comparison with the literature. All those compounds are been reported for the first time in Mauritia, and the chemosystematic significance of the flavonoids isolated in this genus is discussed.

  13. Triterpenes and flavonoids from the roots of Mauritia flexuosa

    Directory of Open Access Journals (Sweden)

    Hector H. F. Koolen

    2012-02-01

    Full Text Available Mauritia flexuosa L. f., Arecaceae, is an endemic species of South America. This species was studied with the intent to isolate the constituents of its roots. After the fractionation of the n-hexane and methanolic extracts from the roots of M. flexuosa, six triterpenes were obtained: friedelin, taraxerone, lupenyl acetate, lupenone, betulin and betulinic acid, along with three flavonoids: rutin, quercitrin and quercetin. All the compounds were identified by analysis of NMR and MS data and comparison with the literature. All those compounds are been reported for the first time in Mauritia, and the chemosystematic significance of the flavonoids isolated in this genus is discussed.

  14. Dirhamnosyl flavonoid and other constituents from Brillantaisia palisatii

    Energy Technology Data Exchange (ETDEWEB)

    Berrondo, Luciane Fatima; Gabriel, Felipe Teixeira; Fernandes, Sidney Bessa de; Menezes, Fabio de Sousa [Universidade Federal, Rio de Janeiro, RJ (Brazil). Faculdade de Farmacia. Dept. de Produtos Naturais e Alimentos]. E-mail: fsmenezes@pharma.ufrj.br; Moreira, Davyson de Lima [Universidade de Barra Mansa, RJ (Brazil). Faculdade de Farmacia

    2003-12-01

    A mixture containing sitosterol and stigmasterol; a new triterpene 3-epi-ursolic acid; another triterpene mixture comprising {alpha}-amyrin, {beta}-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. (author)

  15. 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.

  16. 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.

  17. 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.

  18. Larvicidal activity and GC-MS analysis of flavonoids of Vitex negundo and Andrographis paniculata against two vector mosquitoes Anopheles stephensi and Aedes aegypti.

    Science.gov (United States)

    Gautam, Keerti; Kumar, Padma; Poonia, Sawitri

    2013-09-01

    Development of insect resistance to synthetic pesticides, high operational cost and environmental pollution have created the need for developing alternative approaches to control vector-borne diseases. In the present study, larvicidal activity of flavonoid extracts of different parts of Vitex negundo (Linnaeus) and Andrographis paniculata (Nees) have been studied against the late III or early IV instar larvae of Aedes aegypti and Anopheles stephensi (Liston). Flavonoids were extracted from different parts of the selected plants using standard method. Bioassay test was carried out by WHO method for determination of larvicidal activity against mosquitoes. Different compounds of the most active extract were identified by the gas chromatography-mass spectrometry (GC-MS) analysis. Flavonoid extract of whole aerial part of A. paniculata was found to be inactive against the selected larvae of Ae. aegypti even at the concentration of 600 ppm, whereas it caused 70% mortality in An. stephensi at the concentration of 200 ppm. Flavonoid extract of flower-buds produced highest mortality (100%) at the concentration of 600 ppm for the late III or early IV instar larvae of Ae. aegypti and at the concentration of 200 ppm for the larvae of An. stephensi. GC-MS analysis of the most active flavonoid extract from flower-buds of Vitex showed 81 peaks. Phenol (26.83% area), naphthalene (4.95% area), 2,3-dihydrobenzofuran (6.79% area), Phenol-2,4-Bis (1,1-dimethyl) (4.49% area), flavones 4'-OH,5-OH,7-di-O-glucoside (0.25% area) and 5-hydroxy- 3,6,7,3',4'-pentamethoxy flavones (0.80% area) were present in major amount. Flavonoid extracts from different parts of two selected plants possess larvicidal activity against two selected mosquito species, hence, could be utilized for developing flavonoid-based, eco-friendly insecticide as an alternative to synthetic insecticides.

  19. Compare the amount of phenols, flavonoids and antioxidant activity of five varieties of Iranian olive leaf hydroalcholic extract

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    B mohammadi

    2016-01-01

    Full Text Available Background & aim: Olive leaf extract can be used as a rich source of the polyphenolic antioxidant. The present study aimed to compare the amount of phenols, flavonoids and antioxidant activity of five varieties of Iranian olive leaf hydro alcholic extract . Methods: In the present experimental study, leaves of five Iranian olives  which are raised in five different regions in Iran (Dezfooli variety in gachsaran, Dehghan variety in the region Nurabad mamasani, Shenge variety in kazeron, Shirazi variety in Shiraz, Feshomi vareity in Roodbar in Gilan region was collected. All samples were prepared in spring, then dried in the shade at 28-26 °C . Hydroalcholic extract was obtained with 70% ethanol with maceration method for 24 hours at a temperature of 40-37 °C.Total phenol contents ( Folin-Ciocalteu  and, Flavonoids ( zishen was determined.  Antioxidant activity of the olive leaves extract was evaluated by radical scavenging DPPH method and vitamin C applied as standard .Data were analyzed by the SPSS software (version 21 and significant level (P˂0.05 and 95% confidence intervals were considered. Results: The total phenol and flavonoid content were different in five varieties of olive leaf extract. The highest level of total phenol and flavonoids were reported (212.54 ± 3 in Dezfooli olive variety (900.13±3.28 Shirazi olive variety.  Respectively. The antioxidant activity was different in all vareity. Dezfooli olive variety have the highest antioxidant activity (%71.27 and Shirazi olive variety (%37.29 had the least antioxidant activity with DPPH method. The high relationship was found between the total phenol and antioxidant activity in extracts. Conclusion:  Antioxidant activity, total phenol and flavonoid content were different in each plant extract and a high correlation was found between total phenol and Antioxidant activity

  20. Physico-chemical study of flavonoids from different matureness corn silk material

    OpenAIRE

    Li, Peng; Lapčík, Lubomír; Lapčíková, Barbora; Kalytchuk, Sergii

    2018-01-01

    There was tested a simple extraction procedure of flavonoids separation from the original corn silk (CS) material. It was found, that the total flavonoids content differs with the extraction time and extraction temperature. There were found different flavonoids contents in extracts prepared from different maturity stages of the original corn silk material (silking stage (CS-S), milky stage (CS-M)). Extracted flavonoids content was quantified by the lutin standardization method by means of col...

  1. Cocoa Flavonoid-Enriched Diet Modulates Systemic and Intestinal Immunoglobulin Synthesis in Adult Lewis Rats

    Directory of Open Access Journals (Sweden)

    Francisco J. Pérez-Cano

    2013-08-01

    Full Text Available Previous studies have reported that a diet containing 10% cocoa, a rich source of flavonoids, has immunomodulatory effects on rats and, among others effects, is able to attenuate the immunoglobulin (Ig synthesis in both systemic and intestinal compartments. The purpose of the present study was focused on investigating whether these effects were attributed exclusively to the flavonoid content or to other compounds present in cocoa. To this end, eight-week-old Lewis rats were fed, for two weeks, either a standard diet or three isoenergetic diets containing increasing proportions of cocoa flavonoids from different sources: one with 0.2% polyphenols from conventional defatted cocoa, and two others with 0.4% and 0.8% polyphenols, respectively, from non-fermented cocoa. Diet intake and body weight were monitored and fecal samples were obtained throughout the study to determine fecal pH, IgA, bacteria proportions, and IgA-coated bacteria. Moreover, IgG and IgM concentrations in serum samples collected during the study were quantified. At the end of the dietary intervention no clear changes of serum IgG or IgM concentrations were quantified, showing few effects of cocoa polyphenol diets at the systemic level. However, in the intestine, all cocoa polyphenol-enriched diets attenuated the age-related increase of both fecal IgA and IgA-coated bacteria, as well as the proportion of bacteria in feces. As these effects were not dependent on the dose of polyphenol present in the diets, other compounds and/or the precise polyphenol composition present in cocoa raw material used for the diets could be key factors in this effect.

  2. 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.

  3. Functional Characterization of a Novel R2R3-MYB Transcription Factor Modulating the Flavonoid Biosynthetic Pathway from Epimedium sagittatum

    Directory of Open Access Journals (Sweden)

    Wenjun Huang

    2017-07-01

    Full Text Available Epimedium species have been widely used both as traditional Chinese medicinal plants and ornamental perennials. Both flavonols, acting as the major bioactive components (BCs and anthocyanins, predominantly contributing to the color diversity of Epimedium flowers belong to different classes of flavonoids. It is well-acknowledged that flavonoid biosynthetic pathway is predominantly regulated by R2R3-MYB transcription factor (TF as well as bHLH TF and WD40 protein at the transcriptional level. MYB TFs specifically regulating anthocyanin or flavonol biosynthetic pathway have been already isolated and functionally characterized from Epimedium sagittatum, but a R2R3-MYB TF involved in regulating both these two pathways has not been functionally characterized to date in Epimedium plants. In this study, we report the functional characterization of EsMYB9, a R2R3-MYB TF previously isolated from E. sagittatum. The previous study indicated that EsMYB9 belongs to a small subfamily of R2R3-MYB TFs containing grape VvMYB5a and VvMYB5b TFs, which regulate flavonoid biosynthetic pathway. The present studies show that overexpression of EsMYB9 in tobacco leads to increased transcript levels of flavonoid pathway genes and increased contents of anthocyanins and flavonols. Yeast two-hybrid assay indicates that the C-terminal region of EsMYB9 contributes to the autoactivation activity, and EsMYB9 interacts with EsTT8 or AtTT8 bHLH regulator. Transient reporter assay shows that EsMYB9 slightly activates the expression of EsCHS (chalcone synthase promoter in transiently transformed leaves of Nicotiana benthamiana, but the addition of AtTT8 or EsTT8 bHLH regulator strongly enhances the transcriptional activation of EsMYB9 against five promoters of the flavonoid pathway genes except EsFLS (flavonol synthase. In addition, co-transformation of EsMYB9 and EsTT8 in transiently transfected tobacco leaves strongly induces the expressions of flavonoid biosynthetic genes. The

  4. A flavonoid mutant of barley (Hordeum vulgare L.) exhibits increased sensitivity to UV-B radiation in the primary leaf

    International Nuclear Information System (INIS)

    Reuber, S.; Bornman, J.F.; Weissenböck, G.

    1996-01-01

    The aim of the present investigation was to define the role of soluble flavonoids as UV-B protectants in the primary leaf of barley (Hordeum vulgare L.). For this purpose we used a mutant line (Ant 287) from the Carlsberg collection of proanthocyanidin-free barley containing only 7% of total extractable flavonoids in the primary leaf as compared to the mother variety (Hiege 550/75). Seven-day-old leaves from plants grown under high visible light with or without supplementary UV-B radiation were used for the determination of UV-B sensitivity. UV-B-induced changes were assessed from parameters of chlorophyll fluorescence of photosystem II, including initial and maximum fluorescence, apparent quantum yield, and photochemical and non-photochemical quenching. A quartz fibre-optic microprobe was used to evaluate the amount of potentially harmful UV-B (310 nm radiation) penetrating into the leaf as a direct consequence of flavonoid deficiency. Our data indicate an essential role of flavonoids in UV-B protection of barley primary leaves. In leaves of the mutant line grown under supplementary UV-B, an increase in 310nm radiation in the mesophyll and a strong decrease in the quantum yield of photosynthesis were observed as compared to the corresponding mother variety. Primary leaves of liege responded to supplementary UV-B radiation with a 30% increase in the major flavonoid saponarin and a 500% increase in the minor compound lutonarin. This is assumed to be an efficient protective response since no changes in variable chlorophyll fluorescence were apparent. In addition, a further reduction in UV-B penetration into the mesophyll was recorded in these leaves

  5. Flavonoid Composition and Antitumor Activity of Bee Bread Collected in Northeast Portugal

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    Filipa Sobral

    2017-02-01

    Full Text Available Bee bread (BB is a fermented mixture of plant pollen, honey, and bee saliva that worker bees use as food for larvae, and for young bees to produce royal jelly. In the present study, five BB samples, collected from Apis mellifera iberiensis hives located in different apiaries near Bragança, in the northeast region of Portugal, and one BB commercial sample were characterized by high-performance liquid chromatography coupled to a diode array detector and electrospray mass spectrometry (HPLC-DAD-ESI/MS in terms of phenolic compounds, such as flavonoid glycoside derivatives. Furthermore, the samples were screened, using in vitro assays, against different human tumor cell lines, MCF-7 (breast adenocarcinoma, NCI-H460 (non-small cell lung cancer, HeLa (cervical carcinoma and HepG2 (hepatocellular carcinoma, and also against non-tumor liver cells (porcine liver cells, PLP2. The main phenolic compounds found were flavonol derivatives, mainly quercetin, kaempferol, myricetin, isorhamnetin and herbacetrin glycoside derivatives. Thirty-two compounds were identified in the six BB samples, presenting BB1 and BB3 with the highest contents (6802 and 6480 µg/g extract, respectively and the highest number of identified compounds. Two isorhamnetin glycoside derivatives, isrohamnetin-O-hexosyl-O-rutinoside and isorhamnetin-O-pentosyl-hexoside, were the most abundant compounds present in BB1; on the other hand, quercetin-3-O-rhamnoside was the most abundant flavonol in BB3. However, it was not possible to establish a correlation between the flavonoids and the observed low to moderate cytotoxicity (ranging from >400 to 68 µg/mL, in which HeLa and NCI-H460 cell lines were the most susceptible to the inhibition. To the authors’ knowledge, this is the first report characterizing glycosidic flavonoids in BB samples, contributing to the chemical knowledge of this less explored bee product.

  6. Cocoa and chocolate flavonoids: implications for cardiovascular health.

    Science.gov (United States)

    Steinberg, Francene M; Bearden, Monica M; Keen, Carl L

    2003-02-01

    This paper offers a review of current scientific research regarding the potential cardiovascular health benefits of flavonoids found in cocoa and chocolate. Recent reports indicate that the main flavonoids found in cocoa, flavan-3-ols and their oligomeric derivatives, procyanidins, have a variety of beneficial actions, including antioxidant protection and modulation of vascular homeostasis. These findings are supported by similar research on other flavonoid-rich foods. Other constituents in cocoa and chocolate that may also influence cardiovascular health are briefly reviewed. The lipid content of chocolate is relatively high; however, one third of the lipid in cocoa butter is composed of the fat stearic acid, which exerts a neutral cholesterolemic response in humans. Cocoa and chocolate contribute to trace mineral intake, which is necessary for optimum functioning of all biologic systems and for vascular tone. Thus, multiple components in chocolate, particularly flavonoids, can contribute to the complex interplay of nutrition and health. Applications of this knowledge include recommendations by health professionals to encourage individuals to consume a wide range of phytochemical-rich foods, which can include dark chocolate in moderate amounts.

  7. 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, ...

  8. 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

  9. 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...

  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. 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 ...

  12. 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.

  13. 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.

  14. 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...

  15. Antioxidant and Anti-proliferative Activities of Flavonoids from ...

    African Journals Online (AJOL)

    significant growth inhibitory effect on RKO cells with IC50 of 39.08 μmol/L and 17.68 μmol/L, respectively ..... YJ.. Essential oil from rhizomes of Ligusticum chuanxiong induces apoptosis in hypertrophic scar ... Liu H, Mou Y, Zhao J, Wang J, Zhou L, Wang M, Wang. D, Han J, Yu Z, Yang F. Flavonoids from Halostachys.

  16. Flavonoid biosynthesis controls fiber color in naturally colored cotton

    Directory of Open Access Journals (Sweden)

    Hai-Feng Liu

    2018-04-01

    Full Text Available The existence of only natural brown and green cotton fibers (BCF and GCF, respectively, as well as poor fiber quality, limits the use of naturally colored cotton (Gossypium hirsutum L.. A better understanding of fiber pigment regulation is needed to surmount these obstacles. In this work, transcriptome analysis and quantitative reverse transcription PCR revealed that 13 and 9 phenylpropanoid (metabolic pathway genes were enriched during pigment synthesis, while the differential expression of phenylpropanoid (metabolic and flavonoid metabolic pathway genes occurred among BCF, GCF, and white cotton fibers (WCF. Silencing the chalcone flavanone isomerase gene in a BCF line resulted in three fiber phenotypes among offspring of the RNAi lines: BCF, almost WCF, and GCF. The lines with almost WCF suppressed chalcone flavanone isomerase, while the lines with GCF highly expressed the glucosyl transferase (3GT gene. Overexpression of the Gh3GT or Arabidopsis thaliana 3GT gene in BCF lines resulted in GCF. Additionally, the phenylpropanoid and flavonoid metabolites of BCF and GCF were significantly higher than those of WCF as assessed by a metabolomics analysis. Thus, the flavonoid biosynthetic pathway controls both brown and green pigmentation processes. Like natural colored fibers, the transgenic colored fibers were weaker and shorter than WCF. This study shows the potential of flavonoid pathway modifications to alter cotton fibers’ color and quality.

  17. A quantum chemical explanation of the antioxidant activity af flavonoids.

    NARCIS (Netherlands)

    van Acker, S.A.B.E.; de Groot, M.J.; van den Berg, D.J.; Tromp, M.N.J.L.; Donné-Op den Kelder, G.M.; van der Vijgh, W.J.F.; Bast, A.

    1996-01-01

    Flavonoids are a group of naturally occurring antioxidants, which over the past years have gained tremendous interest because of their possible therapeutic applicability. The mechanism of their antioxidant activity has been extensively studied over several decades. However, there is still much

  18. 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 ...

  19. 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.

  20. Effect of citrus flavonoids on HL-60 cell differentiation.

    Science.gov (United States)

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

    1999-01-01

    Twenty-seven Citrus flavonoids were examined for their activity of induction of terminal differentiation of human promyelocytic leukemia cells (HL-60) by nitro blue tetrazolium (NBT) reducing, nonspecific esterase, specific esterase, and phagocytic activities. 10 flavonoids were judged to be active (percentage of NBT reducing cells was more than 40% at a concentration of 40 microM), and the rank order of potency was natsudaidain, luteolin, tangeretin, quercetin, apigenin, 3, 3, '4, '5, 6, 7, 8-heptamethoxyflavone, nobiletin, acacetin, eriodictyol, and taxifolin. These flavonoids exerted their activity in a dose-dependent manner. HL-60 cells treated with these flavonoids differentiated into mature monocyte/macrophage. The structure-activity relationship established from comparison between flavones and flavanones revealed that ortho-catechol moiety in ring B and C2-C3 double bond had an important role for induction of differentiation of HL-60. In polymethoxylated flavones, hydroxyl group at C3 and methoxyl group at C8 enhanced the differentiation-inducing activity.

  1. 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 ...

  2. 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 ...

  3. 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, λmax = 1270 nm, following laser excitation and steady-state methods were employed to measure the total reaction rate constant, kT, and the reactive reaction rate constant, kr, for the reaction between singlet oxygen and several flavonoids. Values of kT determined in deuterated water, ranging from 2.4×107 M−1s−1 to 13.4×107 M−1s−1, for rutin and morin, respectively, and the values measured for kr, ranging from 2.8×105 M−1s−1 to 65.7×105 M−1s−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. PMID:22802966

  4. 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.

  5. 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.

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

    African Journals Online (AJOL)

    Lee WC, Yusof Y, Hamid NSA, Baharin BS. Optimizing conditions for hot water extraction of banana juice using response surface methodology (RSM). J Food. Eng 2006; 75: 473-479. 11. Proestos C, Sereli D, Komaitis M. Analysis of flavonoids and phenolic acids in Greek aromatic plants: Investigation of their antioxidant ...

  7. 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

  8. Quantification of major flavonoids in carnation tissues (Dianthus caryophyllus) as a tool for cultivar discrimination.

    Science.gov (United States)

    Galeotti, Francesco; Barile, Elisa; Lanzotti, Virginia; Dolci, Marcello; Curir, Paolo

    2008-01-01

    One flavone-C-glycoside and two flavonol-O-glycosides were recognized and isolated as the main flavonoidal components in nine different carnation cultivars, and their chemical structures have been determined by spectroscopic methods, including UV detection, MS and NMR. The distribution of these three compounds in flowers, leaves, stems, young sprouts, and roots of each cultivar was evaluated by a simple HPLC-UV method: the graphic representation of their content in the different tissues allows to identify and characterize unambiguously each considered carnation cultivar. The presented method could be an easy, inexpensive and reliable tool for carnation cultivar discrimination.

  9. Habitual intake of dietary flavonoids and risk of Parkinson disease.

    Science.gov (United States)

    Gao, X; Cassidy, A; Schwarzschild, M A; Rimm, E B; Ascherio, A

    2012-04-10

    To prospectively examine whether higher intakes of total flavonoids and their subclasses (flavanones, anthocyanins, flavan-3-ols, flavonols, flavones, and polymers) were associated with a lower risk of developing Parkinson disease (PD). In the current analysis, we included 49,281 men in the Health Professional Follow-up Study and 80,336 women from the Nurses' Health Study. Five major sources of flavonoid-rich foods (tea, berry fruits, apples, red wine, and orange/orange juice) were also examined. Flavonoid intake was assessed using an updated food composition database and a validated food frequency questionnaire. We identified 805 participants (438 men and 367 women) who developed PD during 20-22 years of follow-up. In men, after adjusting for multiple confounders, participants in the highest quintile of total flavonoids had a 40%lower PD risk than those in the lowest quintile (hazard ratio [HR] = 0.60; 95% confidence interval 0.43, 0.83; p trend = 0.001). No significant relationship was observed in women (p trend = 0.62) or in pooled analyses (p trend = 0.23). In the pooled analyses for the subclasses, intakes of anthocyanins and a rich dietary source, berries, were significantly associated with a lower PD risk (HR comparing 2 extreme intake quintiles were 0.76 for anthocyanins and 0.77 for berries, respectively; p trend < 0.02 for both). Our findings suggest that intake of some flavonoids may reduce PD risk, particularly in men, but a protective effect of other constituents of plant foods cannot be excluded.

  10. [Seasonal changes and response to stress of total flavonoids content of Farfugium japonicum].

    Science.gov (United States)

    Cui, Dalian; Ma, Yuxin

    2013-05-01

    To investigate the seasonal variation of total flavonoid content of Farfugium japonicum and its response to stress. The total flavonoids of Farfugium japonicum were determined by spectrophotometry in different seasons and under various stressful factors. The total flavonoid content in Farfugium japonicum leaves was the highest, followed by the petiole, and rhizomes (Pseasons (Pwater stress, the total flavonoid content in Farfugium japonicum leaves gradually increased, that in petiole first increased and then decreased,while that in rhizomes decreased (Pstress, the total flavonoid content in leaves, petioles and rhizomes of Farfugium japonicum showed a decreasing trend (Pseasons and that in different parts of the plant has different responses to ecological stressful factors.

  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. Flavonoids at the pharma-nutrition interface: Is a therapeutic index in demand?

    Science.gov (United States)

    Peluso, Ilaria; Palmery, Maura

    2015-04-01

    The consumption of flavonoid-rich foods could have beneficial effects on health. However, different classes of flavonoids have different effect on disease risk and the relationship between flavonoid intake and risk of disease appeared to be non-linear. Furthermore, contrarily to vitamins, there are no symptoms of deficiency for flavonoids; therefore, our body treats them like other xenobiotics. Therefore, a therapeutic index should be determined. Despite flavonoids are at the pharma-nutrition interface, drugs and foods are subject to different regulatory frameworks and there is no recommended daily allowance (RDA) for flavonoids. Relatively little is known about the efficacy, safety and underlying mechanisms of these bioactive compounds, especially when taken in concert with drugs. Flavonoids could act both as drugs and pro-drugs with pharmacological and toxicological promiscuity. Due to the low bioavailability, the gastrointestinal tract could be the primary target of flavonoids and metabolites. Different effects have been observed after acute and chronic consumption and bioavailability and bioactivity have high inter-individual variability. Furthermore, the difficulties in the design and in the interpretation of human intervention studies make difficult the establishment of a therapeutic index for flavonoids. Probably the concept of 'personalized nutrition' previously proposed could be the better approach. However, despite more studies are needed in order to establish a therapeutic index for each flavonoid subclasses, at the moment RDA of total flavonoids could be between 250-400 mg/d, respecting the seasonality of food sources. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

  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

    Directory of Open Access Journals (Sweden)

    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. Dietary total flavonoids intake and risk of mortality from all causes and cardiovascular disease in the general population: A systematic review and meta-analysis of cohort studies.

    Science.gov (United States)

    Liu, Xue-Ming; Liu, Yu-Jian; Huang, Yao; Yu, Hong-Jie; Yuan, Shuai; Tang, Bo-Wen; Wang, Pei-Gang; He, Qi-Qiang

    2017-06-01

    Epidemiologic studies assessing the association between dietary total flavonoids intake and the risk of mortality from cardiovascular disease (CVD) and all causes have yielded inconsistent results. Therefore, we conducted a dose-response meta-analysis to investigate this association. We searched PubMed and Embase databases from January 1966 through May 2016 and examined the references of retrieved articles to identify relevant prospective cohort studies. The random-effect model was used to calculate the summary risk estimates and dose-response analysis was performed. Ten studies were included in the present meta-analysis. The relative risk (RR) of all-cause mortality for the highest versus lowest category of total flavonoids intake was 0.82 (95% confidence interval (CI): 0.72-0.92). Dose-response analysis showed that those consuming 200 mg/day of total flavonoids had the lowest risk of all-cause mortality. Furthermore, a marginally significant association was found between dietary total flavonoids consumption and risk of death from CVD (summary RR: 0.85; 95% CI: 0.70-1.03; P = 0.099) and coronary heart diseases (summary RR: 0.74; 95% CI: 0.54-1.02; P = 0.069), respectively. The meta-analysis provides strong evidence for the recommendation of consuming flavonoids-rich food to reduce risks of mortality from all causes as part of a healthy diet among general adults. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Effects of synthetic and naturally occurring flavonoids on Na+, K+-ATPase: Aspects of the structure-activity relationship and action mechanism

    International Nuclear Information System (INIS)

    Hirano, T.; Oka, K.; Akiba, M.

    1989-01-01

    A comparative study was made of the effects of 15 synthetic and naturally occurring flavonoids on the hydrolytic activity of Na + , K + -adenosine triphosphatase (ATPase). Twelve of the flavonoids examined were mono-hydroxy or mono-methoxy derivatives. All inhibited Na + , K + -ATPase from dog kidney cortex when present at concentrations from 40-1000 μM. Flavones possessing cyclohexyl instead of the phenyl group were the most potent with IC 50 at 257-320 μM. Structure-activity relationships were observed among the following mono-substituted flavones as: (i) 2-cyclohexyl-benzopyran-4-one much-gt 2-phenyl-benzopyran-4-one; (ii) 2-cyclohexyl-7-hydroxybenzopyran-4-one > 2-cyclohexyl-6-hydroxy-benzopyran-4-one > 2-cyclohexyl-5-hydroxybenzopyran-4-one. Some flavonoids showing potent inhibitory activity were also examined for ouabain-displacement activity on human erythrocytes. Hardly and of the flavonoids were able to block [ 3 H] ouabain binding to erythrocytes. These results suggest that the mechanism by which flavonoid block Na + , K + -ATPase is not related to the cardiac glycoside-specific binding site(s) of this enzyme

  17. Effects of synthetic and naturally occurring flavonoids on Na sup + , K sup + -ATPase: Aspects of the structure-activity relationship and action mechanism

    Energy Technology Data Exchange (ETDEWEB)

    Hirano, T.; Oka, K.; Akiba, M. (Tokyo College of Pharmacy (Japan))

    1989-01-01

    A comparative study was made of the effects of 15 synthetic and naturally occurring flavonoids on the hydrolytic activity of Na{sup +}, K{sup +} -adenosine triphosphatase (ATPase). Twelve of the flavonoids examined were mono-hydroxy or mono-methoxy derivatives. All inhibited Na{sup +}, K{sup +} -ATPase from dog kidney cortex when present at concentrations from 40-1000 {mu}M. Flavones possessing cyclohexyl instead of the phenyl group were the most potent with IC{sub 50} at 257-320 {mu}M. Structure-activity relationships were observed among the following mono-substituted flavones as: (i) 2-cyclohexyl-benzopyran-4-one {much gt} 2-phenyl-benzopyran-4-one; (ii) 2-cyclohexyl-7-hydroxybenzopyran-4-one {gt} 2-cyclohexyl-6-hydroxy-benzopyran-4-one {gt} 2-cyclohexyl-5-hydroxybenzopyran-4-one. Some flavonoids showing potent inhibitory activity were also examined for ouabain-displacement activity on human erythrocytes. Hardly and of the flavonoids were able to block ({sup 3}H) ouabain binding to erythrocytes. These results suggest that the mechanism by which flavonoid block Na{sup +}, K{sup +} -ATPase is not related to the cardiac glycoside-specific binding site(s) of this enzyme.

  18. Dietary administration of the licorice flavonoid isoliquiritigenin deters the growth of MCF-7 cells overexpressing aromatase.

    Science.gov (United States)

    Ye, Lan; Gho, Wai M; Chan, Franky L; Chen, Shiuan; Leung, Lai K

    2009-03-01

    Licorice is the sweet-tasting rhizomes of a bean plant and is quite commonly used in Western countries for culinary purposes, while it is a medicinal herb in China. Many flavonoids have been isolated from licorice, and their pharmacological properties may be applicable in preventive medicine. Overexposure to estrogen has been implicated in the etiology of breast cancer, and cytochrome P450 (CYP) 19 enzyme, or aromatase, catalyzes the rate-limiting reaction. Phytocompounds that are able to inhibit this enzyme may potentially suppress breast cancer development. In the present study the licorice flavonoid isoliquiritigenin (ILN) was shown to be an aromatase inhibitor in recombinant protein and MCF-7 cells stably transfected with CYP19 (MCF-7aro). ILN displayed a K(i) value of around 3 muM, and it also blocked the MCF-7aro cell growth pertaining to the enzyme activity in vitro. Subsequently, the compound administered in diet was given to ovariectomized athymic mice transplanted with MCF-7aro cells. This mouse model is widely accepted for studying postmenopausal breast cancer. The phytochemical significantly deterred the xenograft growth without affecting the body weight. Subsequently, the flavonoid's effect on CYP19 transcriptional control in vitro was also investigated. At the mRNA level, ILN could also suppress the expression in wild-type MCF-7 cells. Reporter gene assay and real-time PCR verified that the transactivity of CYP19 driven by promoters I.3 and II was suppressed in these cells. Deactivation of C/EBP could be the underlying molecular mechanism. Our study demonstrated that ILN was an inhibitor of aromatase and a potential chemopreventive agent against breast cancer.

  19. Ascorbic acid and citric flavonoids for broilers under heat stress: effects on performance and meat quality

    Directory of Open Access Journals (Sweden)

    JEM Peña

    2008-06-01

    Full Text Available The aim of this study was to evaluate the effects of increasing doses of ascorbic acid (AA and citric flavonoids (quercetin and rutin on the performance and meat quality characteristics of broilers submitted to cyclic heat stress. Four-hundred one-day-old female Ross 308 were housed in 40 battery cages a in temperature controlled room. Treatments consisted of 0, 250, 500, and 1000 g/ton on of AA + citric flavonoids. Birds were fed ad libitum until 32 day of age. Beginning on day 14 post-hatch until the end of the experiment, in order to simulate cyclic heat stress, the temperature inside the room was increased to 32°C for 5 hours, and decreased until reaching the comfort temperature corresponding to the age of the animals. Birds were slaughtered at 33 days of age, and carcass and commercial cuts yields were determined. Thighs and boneless breast samples were collected and frozen for subsequent analyses of pH, cooking loss, shear force, color, and Thiobarbituric Acid Reactive Substances (TBARS. Significant differences (p <0.05 were found for feed efficiency from 1 to 7 days of age, with the best values for the birds fed 0 and 250 g/ton on of AA + citric flavonoids. At the end of the experiment, there were no differences in other performance variables, carcass and parts yields, pH, shear force, color and TBARS. The meat of the birds supplemented with 250 g/ton on of product presented the lowest cooking loss.

  20. Anti-obesity and antioxidant activity of dietary flavonoids from Dioscorea steriscus tubers

    Directory of Open Access Journals (Sweden)

    Pamhidzai Dzomba

    2014-06-01

    Full Text Available Objective: To investigate antioxidant and anti-obesity activity of flavonoids extracted by solvent cold percolation and preparative thin liquid chromatography from Dioscorea steriscus tubers. Methods: 1-diphenyl-2-picrylhydrazyl (DPPH antiradical activity was employed to investigate antioxidant activity while chromogenic method was used to determine alpha amylase inhibition activity and spectrophotometric methods using triolein as a substrate was used to investigate lipase activity. Results: Thin liquid chromatography profiling revealed eight different flavonoid types. Ethyl acetate extract yielded two types, Rf values 0.38 and 0.40; chloroform extract also yielded two types Rf values 0.06 and 0.51, while ethanol extract yielded four types with Rf values 0.16, 0.33, 0.65 and 0.96. All the extracted flavonoids exhibited antioxidant activity with ethanol extracts exhibiting the greatest antiradical activity. The order of enzyme inhibition capacity was ethyl acetatepresent study show that Dioscorea steriscus consists of bioactive compounds that can act as lipase and α-amylase inhibitors and therefore can be useful for the development of functional foods against obesity. It can also be used as a source of lead compounds for designing new ant-obesity therapeuticals.

  1. Investigating the synergistic antioxidant effects of some flavonoid and phenolic compounds

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    H. Hajimehdipoor

    2014-04-01

    Full Text Available Phenolic and flavonoid compounds are secondary metabolites of plants which possess various activities such as anti-inflammatory, analgesic, anti-diabetes and anticancer effects. It has been established that these compounds can scavenge free radicals produced in the body. Because of this ability, not only the plants containing phenolic and flavonoid compounds but also, the pure compounds are used in medicinal products for prevention and treatment of many disorders. Considering that the golden aim of the pharmaceutical industries is using the most effective compounds with lower concentrations, determination of the best combination of the compounds with synergistic effects is important. In the present study, synergistic antioxidant effects of four phenolic compounds including caffeic acid, gallic acid, rosmarinic acid, chlorogenic acid and two flavonoids,  rutin and quercetin, have been investigated by FRAP (Ferric Reducing Antioxidant Power method. The synergistic effect was assessed by comparing the experimental antioxidant activity of the mixtures with calculated theoretical values and the interactions of the compounds were determined. The results showed that combination of gallic acid and caffeic acid demonstrated considerable synergistic effects (137.8% while other combinations were less potent. Among examined substances, rutin was the only one which had no effect on the other compounds. The results of ternary combinations of compounds demonstrated antagonistic effects in some cases. This was more considerable in mixture of rutin, caffeic acid, rosmarinic acid (-21.8%, chlorogenic acid, caffeic acid, rosmarinic acid (-20%, rutin, rosmarinic acid, gallic acid (-18.5% and rutin, chlorogenic acid, caffeic acid (-15.8%, while, combination of quercetin, gallic acid, caffeic acid (59.4% and quercetin, gallic acid, rutin (55.2% showed the most synergistic effects. It was concluded that binary and ternary combination of quercetin, rutin, caffeic acid

  2. HPLC identification and determination of myricetin, quercetin, kaempferol and total flavonoids in herbal drugs

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    Svetlana Kulevanova

    2003-05-01

    Full Text Available A new and rapid HPLC method for identification and determination of myricetin, quercetin, kaempferol and total flavonoids in ten herbal drugs of Macedonian origin is presented. Preparation of samples (Uvae ursi folim, Pruni spinosae flos, Sambuci flos, Betulae folim, Primulae flos, Herniariae herba, Centaurii herba, Tiliae flos, Robiniae pseudoacaciae flos, Bursae pastoris herba included hydrolysis of glycosides and extraction of total aglycones with ethyl acetate. HPLC analysis with UV-diode array detection was carried out on RP C18 column, using 5% acetic acid and acetonitrile in agradient elution mode and column temperature of 30 o C. The monitoring of the elution is performed in the whole UV-range and the acquisition of data for quantitative analysis at 367 nm. Screening of the extracts showed presence of quercetin in nine, kaempferol in seven and myricetin in only one sample. The quantitative analysis showed that the content of quercetin ranged from 0.026-0.506 % (m/m, while for kaempferol it was from traces to 1.246 %. Uvaeursi folium and Pruni spinosae flos were rich in content of quercetin (0.482 % and 0.506 %, respectively, while Pruni spinosae flos and Robiniae pseudoaccaciae flos contained the highest amounts of kaempferol (1.246 % and 0.892 %, respectively. Myricetin was identified and determined only in Betulae folium (0.102 %. The content of total flavonoids in the investigated samples expressed in terms of quercetin ranged from 0.040 to 1.680 %. The proposed HPLC method is convenient for use in routine analysis of myricetin, quercetin and kaempferol, as well as for estimation of total flavonoids content in herbal drugs.

  3. 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

  4. Survey of the effect of doxorubicin and flavonoid extract of white Morus alba leaf on apoptosis induction in a-172 GBM cell line.

    Science.gov (United States)

    Dabili, Sheyda; Fallah, Soudabeh; Aein, Mojdeh; Vatannejad, Akram; Panahi, Ghodratollah; Fadaei, Reza; Moradi, Nariman; Shojaii, Asie

    2018-02-20

    In this study, the effect of doxorubicin, flavonoid extract of white Morus alba leaf (MFE) and a combination of doxorubicin and flavonoid extract on Bax and Bcl2 levels and caspase 3 activity of cancer A-172 GBM cell line was investigated. Bax/Bcl2 levels of treated A-172 GBM cell line with flavonoid extract of white mulberry leaf were estimated by ELISA methods. Caspase 3 activity of treated A-172 GBM cells was determined by calorimetric assay. The flow cytometry assessment was used to estimate the apoptosis percent of treated A-172 GBM cells. Treatment of A-172 GBM cells with MFE, doxorubicin and a combination of MFE and doxorubicin caused a significant decrease in Bcl2 level and an increase in Bax level. The apoptosis percent of treated cells were also elevated significantly. Present results suggest that concomitant use of herbal medicine and chemotherapy may be an effective alternative method for the treatment of cancers.

  5. Genetic algorithm as a variable selection procedure for the simulation of 13C nuclear magnetic resonance spectra of flavonoid derivatives using multiple linear regression.

    Science.gov (United States)

    Ghavami, Raoof; Najafi, Amir; Sajadi, Mohammad; Djannaty, Farhad

    2008-09-01

    In order to accurately simulate (13)C NMR spectra of hydroxy, polyhydroxy and methoxy substituted flavonoid a quantitative structure-property relationship (QSPR) model, relating atom-based calculated descriptors to (13)C NMR chemical shifts (ppm, TMS=0), is developed. A dataset consisting of 50 flavonoid derivatives was employed for the present analysis. A set of 417 topological, geometrical, and electronic descriptors representing various structural characteristics was calculated and separate multilinear QSPR models were developed between each carbon atom of flavonoid and the calculated descriptors. Genetic algorithm (GA) and multiple linear regression analysis (MLRA) were used to select the descriptors and to generate the correlation models. Analysis of the results revealed a correlation coefficient and root mean square error (RMSE) of 0.994 and 2.53ppm, respectively, for the prediction set.

  6. Ultraviolet-B Protective Effect of Flavonoids from Eugenia caryophylata on Human Dermal Fibroblast Cells.

    Science.gov (United States)

    Patwardhan, Juilee; Bhatt, Purvi

    2015-10-01

    The exposure of skin to ultraviolet-B (UV-B) radiations leads to deoxyribonucleic acid (DNA) damage and can induce production of free radicals which imbalance the redox status of the cell and lead to increased oxidative stress. Clove has been traditionally used for its analgesic, anti-inflammatory, anti-microbial, anti-viral, and antiseptic effects. To evaluate the UV-B protective activity of flavonoids from Eugenia caryophylata (clove) buds on human dermal fibroblast cells. Protective ability of flavonoid-enriched (FE) fraction of clove was studied against UV-B induced cytotoxicity, anti-oxidant regulation, oxidative DNA damage, intracellular reactive oxygen species (ROS) generation, apoptotic morphological changes, and regulation of heme oxygenase-1 (HO-1) gene through nuclear factor E2-related factor 2 antioxidant response element (Nrf2 ARE) pathway. FE fraction showed a significant antioxidant potential. Pretreatment of cells with FE fraction (10-40 μg/ml) reversed the effects of UV-B induced cytotoxicity, depletion of endogenous enzymatic antioxidants, oxidative DNA damage, intracellular ROS production, apoptotic changes, and overexpression of Nrf2 and HO-1. The present study demonstrated for the first time that the FE fraction from clove could confer UV-B protection probably through the Nrf2-ARE pathway, which included the down-regulation of Nrf2 and HO-1. These findings suggested that the flavonoids from clove could potentially be considered as UV-B protectants and can be explored further for its topical application to the area of the skin requiring protection. Pretreatment of human dermal fibroblast with flavonoid-enriched fraction of Eugenia caryophylata attenuated effects of ultraviolet-B radiationsIt also conferred protection through nuclear factor E2-related factor 2-antioxidant response pathway and increased tolerance of cells against oxidative stressFlavonoid-enriched fraction can be explored further for topical application to the skin as a

  7. Effect of doses of poultry compost on chorophyll and flavonoids of Brachiaria brizantha brs Piatã

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    Alexandre Antonio Pasqualini

    2013-12-01

    Full Text Available In 2012, Brazil produced 12.6 million metric tons of chicken meat, generating 10.3 tons of poultry litter. Compost made from such organic waste can be used as a low-cost bio fertilizer, especially as nitrogen and phosphorus source. The compost can increase pastures quality by giving photosynthetic improvement and altering amounts of chlorophyll and flavonoids.  There is little information about the relationship between chlorophyll a or b and flavonoids in Brachiaria brizantha Piata. The flavonoid is a kind of polyphenol compound which protects the plant against UV-B radiation and pathogen attack, it acts as attractants for pollinators, as signal molecules for initiating plant-microbe symbiotic associations and antioxidant activity. The objective of the present study was verified the effects of poultry litter compost doses on the chlorophyll and flavonoid contents in Piata grass leaves. The experiment was performed at the Animal Nutrition and Pasture Center – Instituto de Zootecnia – Nova Odessa, SP, from May to July 2013, on a Haplorthox soil (pHCaCl2= 4.9, cultivated with Piata grass (Brachiaria brizantha, Stapf, without liming. The treatments consisted of five compost doses: 0; 20; 40; 60 and 120 Mg ha-1, with the following chemical composition (%: 2.88 of N, 3.85 of P2O5, 2.50 of K2O, 9.06 of Ca and 1.16 of Mg. The experimental design was on randomized blocks with five replications.  Chlorophyll amounts and flavonoids were determined by sampling the third medium of the leaf blade from  a third of the expanded leaf from the apical  using the Dualex and the chlorophyll a and b  which were determined by  the Lichtenthaler & Wellburn (1983 method.  Results showed that chlorophyll a was similar in all doses (average of 18.3 micrograms per cm2,therefore for chlorophyll b the amount was significantly increased from 7.3 to 22.4 micrograms per  cm2 (P<0.01when compared to no addition of poultry litter. The fast nitrogen liberation from

  8. Electrochemical quantification of the structure/antioxidant activity relationship of flavonoids

    International Nuclear Information System (INIS)

    Ferreira, Rafael de Queiroz; Greco, Sandro José; Delarmelina, Maicon; Weber, Karen Cacilda

    2015-01-01

    Highlights: • CRAC assay simply and rapidly quantifies the reducing capacity of antioxidant compounds based on the consumption of a standard oxidizer (Ce 4+ ). • The electronic properties of studied flavonoid compounds and their antioxidant activity can be well correlated by this three variables: (i) polarizability, (ii) change at carbon 3’ (iii) change at carbon 5. • Hierarchical antioxidant classification generated by CRAC assay: morin > kaempferol ≅ quercetin > fisetin > apigenin > luteolin > catechin > chrysin. • Antioxidant hierarchy for groups present in the studied flavonoids compound generated by CRAC assay: OH(C2′C4′) > OH(C4′) ≅ OH(C3′C4′) > C2=C3 + 4-oxo > OH(C3,C5) + 4-oxo > OH(C3) + 4-oxo > OH(C5) + 4-oxo > OH(C3,C5). - Abstract: Ceric Reducing/Antioxidant Capacity (CRAC) is an electrochemical test that has recently emerged as an alternative to the spectrophotometric tests employed in the determination of antioxidant capacity. CRAC simply and rapidly quantifies the reducing capacity of antioxidant compounds based on the consumption of a standard oxidizer (Ce 4+ ). In this study, eight samples of flavonoids from three distinct groups were evaluated and showed the following antioxidant hierarchy: morin > kaempferol ≅ quercetin > fisetin > apigenin > luteolin > catechin > chrysin. This hierarchy is correlated with the behavior expected according to the structure/antioxidant activity relationship (SAR) of these polyphenolic compounds. Additionally, other correlations were established using SAR to explain the antioxidant behavior of the compounds with unrelated groups: OH(C2′C4′) > OH(C4′) ≅ OH(C3′C4′) > C2 = C3 + 4-oxo > OH(C3,C5) + 4-oxo > OH(C3) + 4-oxo > OH(C5) + 4-oxo > OH(C3,C5). Therefore, the use of these two tools together is very important for the study of the antioxidant behavior of flavonoids, contributing uniquely to the understanding of electronic transfer mechanisms involved in the antioxidant processes

  9. Infusions of artichoke and milk thistle represent a good source of phenolic acids and flavonoids.

    Science.gov (United States)

    Pereira, Carla; Barros, Lillian; Carvalho, Ana Maria; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2015-01-01

    Cynara scolymus L. (artichoke) and Silybum marianum (L.) Gaertn (milk thistle) are two herbs well-known for their efficiency in the prevention/treatment of liver injuries, among other chronic diseases. Therefore, the aim of this work was to characterize specific bioactive components, phenolic compounds, in hydromethanolic extracts but also in infusions (the most commonly used preparations) obtained from the whole plant of milk thistle and artichoke. The phenolic profiles were accessed using HPLC-DAD-MS/ESI. Infusions of both species presented higher phenolic contents than the hydromethanolic extracts. Milk thistle presented a similar phenolic composition between the two preparations, revealing only differences in the quantities obtained. Nevertheless, artichoke revealed a slightly different profile considering infusion and hydromethanolic extracts. Apigenin-7-O-glucuronide was the major flavonoid found in milk thistle, while luteolin-7-O-glucuronide was the most abundant in artichoke. Therefore, infusions of both artichoke and milk thistle represent a good source of bioactive compounds, especially phenolic acids and flavonoids.

  10. Flavonoides glicosilados de Erythroxylum pulchrum a. st.-hil. (Erythroxylaceae

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    Camila Holanda de Albuquerque

    2014-01-01

    Full Text Available 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.

  11. 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)

  12. PHYSIOLOGICAL AND MEDICAL EFFECTS OF PLANT FLAVONOID QUERCETIN

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    Aneta Štochmaľová

    2013-02-01

    Full Text Available Flavonoid compounds in vegetable-based diets bring a significant contribution to the role of fruits and vegetables as health-promoting foods. This review summarizes the available data concerning physiological and therapeutical effect of plan flavonoid quercetin. Quercetin has a number of beneficial influence on health because of their antioxidant, anti-inflammatory, anti-proliferative, anti-carcinogenic and anti-diabetes properties. Effects of quercetin have been explained by its interference with cellular enzymes, receptors, transporters and signal transduction systems. Despite the available data reviewed here, the targets, effects, absorption, metabolism and areas of practical application of quercetin are still poorly understood, therefore further studies in this areas are required.

  13. Antiproliferative activity of flavonoids on several cancer cell lines.

    Science.gov (United States)

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

    1999-05-01

    Twenty-seven Citrus flavonoids were examined for their antiproliferative activities against several tumor and normal human cell lines. As a result, 7 flavonoids were judged to be active against the tumor cell lines, while they had weak antiproliferative activity against the normal human cell lines. The rank order of potency was luteolin, natsudaidain, quercetin, tangeretin, eriodictyol, nobiletin, and 3,3',4',5,6,7,8-heptamethoxyflavone. The structure-activity relationship established from comparison among these flavones and flavanones showed that the ortho-catechol moiety in ring B and a C2-C3 double bond were important for the antiproliferative activity. As to polymethoxylated flavones, C-3 hydroxyl and C-8 methoxyl groups were essential for high activity.

  14. Flavonoids and fatty acids of Camellia japonica leaves extract

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    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.

  15. 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.

  16. Flavonoids from Artemisia annua L. as Antioxidants and Their Potential Synergism with Artemisinin against Malaria and Cancer

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    Jorge F.S. Ferreira

    2010-04-01

    Full Text Available Artemisia annua is currently the only commercial source of the sesquiterpene lactone artemisinin.Since artemisinin was discovered as the active component of A. annua in early 1970s, hundreds of papers have focused on the anti-parasitic effects of artemisinin and its semi-synthetic analogs dihydroartemisinin, artemether, arteether, and artesunate. Artemisinin per se has not been used in mainstream clinical practice due to its poor bioavailability when compared to its analogs. In the past decade, the work with artemisinin-based compounds has expanded to their anti-cancer properties. Although artemisinin is a major bioactive component present in the traditional Chinese herbal preparations (tea, leaf flavonoids, also present in the tea, have shown a variety of biological activities and may synergize the effects of artemisinin against malaria and cancer. However, only a few studies have focused on the potential synergistic effects between flavonoids and artemisinin. The resurgent idea that multi-component drug therapy might be better than monotherapy is illustrated by the recent resolution of the World Health Organization to support artemisinin-based combination therapies (ACT, instead of the previously used monotherapy with artemisinins. In this critical review we will discuss the possibility that artemisinin and its semi-synthetic analogs might become more effective to treat parasitic diseases (such as malaria and cancer if simultaneously delivered with flavonoids. The flavonoids present in A. annua leaves have been linked to suppression of CYP450 enzymes responsible for altering the absorption and metabolism of artemisinin in the body, but also have been linked to a beneficial immunomodulatory activity in subjects afflicted with parasitic and chronic diseases.

  17. Contenido de flavonoides y compuestos fenólicos de mieles chilenas e índice antioxidante Content of flavonoids and phenolic compounds in chilean honeys. Orac index

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    Orlando Muñoz

    2007-08-01

    Full Text Available A comparison of the phenolic content of several Chilean honeys showed great variations in flavonoid concentration among the samples analysed. Higher amounts of phenolics are found in honey from dry climates. The antioxidant effect of extracts, using ORAC analysis, did not correlate with the flavonoid content or with the total phenolic concentration.

  18. 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)

  19. 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

  20. 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 ...

  1. Flavonoids in the leaves of Asclepias incarnata L.

    Science.gov (United States)

    Sikorska, Maria

    2003-01-01

    Seven flavonoid compounds: quercelin 3-O-beta-galactopyranoside, 3-O-beta-glucopyranoside, 3-O-arabinoside, 3-O-beta-glucopyranosyl (1-->2)-beta-galactopyranoside, 3-O-beta-xylopyranosyl (1-->2)-beta-galactopyranoside, 3-O-alpha-rhamnopyranosyl (1-->2)-beta-galactopyranoside and kaempferol 3-beta-glucopyranoside were isolated and identified from the leaves of Asclepias incarnata, L. (Asclepiadaceae).

  2. FUNCTIONAL SPECIALIZATION OF DUPLICATED FLAVONOID BIOSYNTHESIS GENES IN WHEAT

    Directory of Open Access Journals (Sweden)

    Khlestkina E.

    2012-08-01

    Full Text Available Gene duplication followed by subfunctionalization and neofunctionalization is of a great evolutionary importance. In plant genomes, duplicated genes may result from either polyploidization (homoeologous genes or segmental chromosome duplications (paralogous genes. In allohexaploid wheat Triticum aestivum L. (2n=6x=42, genome BBAADD, both homoeologous and paralogous copies were found for the regulatory gene Myc encoding MYC-like transcriptional factor in the biosynthesis of flavonoid pigments, anthocyanins, and for the structural gene F3h encoding one of the key enzymes of flavonoid biosynthesis, flavanone 3-hydroxylase. From the 5 copies (3 homoeologous and 2 paralogous of the Myc gene found in T. aestivum, only one plays a regulatory role in anthocyanin biosynthesis, interacting complementary with another transcriptional factor (MYB-like to confer purple pigmentation of grain pericarp in wheat. The role and functionality of the other 4 copies of the Myc gene remain unknown. From the 4 functional copies of the F3h gene in T. aestivum, three homoeologues have similar function. They are expressed in wheat organs colored with anthocyanins or in the endosperm, participating there in biosynthesis of uncolored flavonoid substances. The fourth copy (the B-genomic paralogue is transcribed neither in wheat organs colored with anthocyanins nor in seeds, however, it’s expression has been noticed in roots of aluminium-stressed plants, where the three homoeologous copies are not active. Functional diversification of the duplicated flavonoid biosynthesis genes in wheat may be a reason for maintenance of the duplicated copies and preventing them from pseudogenization.The study was supported by RFBR (11-04-92707. We also thank Ms. Galina Generalova for technical assistance.

  3. 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...

  4. Citrus Flavonoid Supplementation Improves Exercise Performance in Trained Athletes

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    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.

  5. 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.

  6. Mutagenicity of Flavonoids Assayed by Bacterial Reverse Mutation (Ames Test

    Directory of Open Access Journals (Sweden)

    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.

  7. Analysis of Flavonoids in Rhamnus davurica and Its Antiproliferative Activities

    Directory of Open Access Journals (Sweden)

    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.

  8. 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®.

  9. 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.

  10. 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

  11. 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

  12. Silver complexation and tandem mass spectrometry for differentiation of isomeric flavonoid diglycosides.

    Science.gov (United States)

    Zhang, Junmei; Brodbelt, Jennifer S

    2005-03-15

    For detection and differentiation of isomeric flavonoids, electrospray ionization mass spectrometry is used to generate silver complexes of the type (Ag + flavonoid)+. Collisionally activated dissociation (CAD) of the resulting 1:1 silver/flavonoid complexes allows isomer differentiation of flavonoids. Eighteen flavonoid diglycosides constituting seven isomeric series are distinguishable from each other based on the CAD patterns of their silver complexes. Characteristic dissociation pathways allow identification of the site of glycosylation, the type of disaccharide (rutinose versus neohesperidose), and the type of aglycon (flavonol versus flavone versus flavanone). This silver complexation method is more universal than previous metal complexation methods, as intense silver complexes are observed even for flavonoids that lack the typical metal chelation sites. To demonstrate the feasibility of using silver complexation and tandem mass spectrometry to characterize flavonoids in complex mixtures, flavonoids extracted from grapefruit juice are separated by high-performance liquid chromatography and analyzed via a postcolumn complexation ESI-MS/MS strategy. Diagnostic fragmentation pathways of the silver complexes of the individual eluting flavonoids allow successful identification of the six flavonoids in the extract.

  13. Dietary flavonoid derivatives enhance chemotherapeutic effect by inhibiting the DNA damage response pathway

    Energy Technology Data Exchange (ETDEWEB)

    Kuo, Ching-Ying [Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan (China); Zupkó, István [Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös Utca 6, Szeged H-6720 (Hungary); Chang, Fang-Rong [Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan (China); Hunyadi, Attila [Institute of Pharmacognosy, Faculty of Pharmacy, University of Szeged, Eötvös Utca 6, Szeged H-6720 (Hungary); Wu, Chin-Chung; Weng, Teng-Song [Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan (China); Wang, Hui-Chun, E-mail: wanghc@kmu.edu.tw [Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan (China); PhD Program in Translational Medicine, College of Medicine and PhD Program in Toxicology, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan (China); Research Center for Natural Product and Drug Development, Kaohsiung Medical University, Kaohsiung 80708, Taiwan (China); Translational Research Center and Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung 80756, Taiwan (China); Department of Marine Biotechnology and Resources, National Sun Yat-Sen University, Kaohsiung 80424, Taiwan (China); Department of Fragrance and Cosmetic Science, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan (China)

    2016-11-15

    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.

  14. Flavonoids and Melanins: a common strategy across two kingdoms.

    Science.gov (United States)

    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 free radical scavenging mechanisms. Both are phenol compounds constitutively synthesized and enhanced after exposure to UV rays, often conferring a red-brown-dark tissue pigmentation. Noteworthy, beside anti-oxidant scavenging activity, melanins and flavonoids have acquired secondary functions that, both in plants and animals, concern reproductions and fitness. Plants highly pigmented are more resistant to biotic and abiotic stresses. Darker wild vertebrates are generally more aggressive, sexually active and resistant to stress than lighter individuals. Flavonoids have been associated with signal attraction between flowers and insects and with plant-plant interaction. Melanin pigmentation has been proposed as trait in bird communication, acting as honest signals of quality. This review shows how the molecular mechanisms leading to tissue pigmentation have many functional analogies between plants and animals and how their origin lies in simpler organisms such as Cyanobacteria. Comparative studies between plant and animal kingdoms can reveal new insight of the antioxidant strategies in vivant.

  15. 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.

  16. 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.

  17. Antiproliferative Activity of Flavonoids from Croton sphaerogynus Baill. (Euphorbiaceae

    Directory of Open Access Journals (Sweden)

    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.

  18. Isolation and identification of phytoestrogens and flavonoids in an Ayurvedic proprietary medicine using chromatographic and Mass Spectroscopic analysis

    Institute of Scientific and Technical Information of China (English)

    Sulaiman CT; Arun A; Anandan EM; Sandhya CR; Indira Balachandran

    2015-01-01

    Objective: To develop analytical methods for the isolation and structural identification of poly phenols including phytoestrogens in Mensokot tablet, a herbal proprietary medicine. Methods:Isolation consisted of an ultrasound-assisted extraction, followed by acid hydrolysis and a final liquid-liquid extraction step in diethyl ether. Identification and structural characterisation was done by liquid chromatography coupled with Q-TOF-ESI-MS/MS analysis. Results:Phytoestrogens such as Coumestrol, Genistein and Glycitein have been identified in Mensokot tablet along with several other flavonoids. Conclusion: In the present research, a rapid HPLC-MS/MS method has been developed for the identification of phytoestrogens and other flavonoids from an Ayurvedic proprietary medicine. Phytoestrogens are considered to play an important role in the prevention of cancers, heart disease, menopausal symptoms and osteoporosis.

  19. Effects of flavonoids on intestinal inflammation, barrier integrity and changes in gut microbiota during diet-induced obesity.

    Science.gov (United States)

    Gil-Cardoso, Katherine; Ginés, Iris; Pinent, Montserrat; Ardévol, Anna; Blay, Mayte; Terra, Ximena

    2016-12-01

    Diet-induced obesity is associated with low-grade inflammation, which, in most cases, leads to the development of metabolic disorders, primarily insulin resistance and type 2 diabetes. Although prior studies have implicated the adipose tissue as being primarily responsible for obesity-associated inflammation, the latest discoveries have correlated impairments in intestinal immune homeostasis and the mucosal barrier with increased activation of the inflammatory pathways and the development of insulin resistance. Therefore, it is essential to define the mechanisms underlying the obesity-associated gut alterations to develop therapies to prevent and treat obesity and its associated diseases. Flavonoids appear to be promising candidates among the natural preventive treatments that have been identified to date. They have been shown to protect against several diseases, including CVD and various cancers. Furthermore, they have clear anti-inflammatory properties, which have primarily been evaluated in non-intestinal models. At present, a growing body of evidence suggests that flavonoids could exert a protective role against obesity-associated pathologies by modulating inflammatory-related cellular events in the intestine and/or the composition of the microbiota populations. The present paper will review the literature to date that has described the protective effects of flavonoids on intestinal inflammation, barrier integrity and gut microbiota in studies conducted using in vivo and in vitro models.

  20. 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)

  1. Anti-HIV-1 activity of flavonoid myricetin on HIV-1 infection in a dual-chamber in vitro model.

    Directory of Open Access Journals (Sweden)

    Silvana Pasetto

    Full Text Available HIV infection by sexual transmission remains an enormous global health concern. More than 1 million new infections among women occur annually. Microbicides represent a promising prevention strategy that women can easily control. Among emerging therapies, natural small molecules such as flavonoids are an important source of new active substances. In this study we report the in vitro cytotoxicity and anti-HIV-1 and microbicide activity of the following flavonoids: Myricetin, Quercetin and Pinocembrin. Cytotoxicity tests were conducted on TZM-bl, HeLa, PBMC, and H9 cell cultures using 0.01-100 µM concentrations. Myricetin presented the lowest toxic effect, with Quercetin and Pinocembrin relatively more toxic. The anti-HIV-1 activity was tested with TZM-bl cell plus HIV-1 BaL (R5 tropic, H9 and PBMC cells plus HIV-1 MN (X4 tropic, and the dual tropic (X4R5 HIV-1 89.6. All flavonoids showed anti-HIV activity, although Myricetin was more effective than Quercetin or Pinocembrin. In TZM-bl cells, Myricetin inhibited ≥90% of HIV-1 BaL infection. The results were confirmed by quantification of HIV-1 p24 antigen in supernatant from H9 and PBMC cells following flavonoid treatment. In H9 and PBMC cells infected by HIV-1 MN and HIV-1 89.6, Myricetin showed more than 80% anti-HIV activity. Quercetin and Pinocembrin presented modest anti-HIV activity in all experiments. Myricetin activity was tested against HIV-RT and inhibited the enzyme by 49%. Microbicide activities were evaluated using a dual-chamber female genital tract model. In the in vitro microbicide activity model, Myricetin showed promising results against different strains of HIV-1 while also showing insignificant cytotoxic effects. Further studies of Myricetin should be performed to identify its molecular targets in order to provide a solid biological foundation for translational research.

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

    African Journals Online (AJOL)

    Protein expression of Bcl2 was almost completely inhibited upon the treatment with 25 μM pectolinarigenin. Conclusion: A rapid method to isolate high purity pectolinarigenin from C. japonicum and as well as evaluate its anti-proliferative potential and induction of apoptosis in MCF-7 breast cancer cells is presented for the ...

  3. Histolocalization and physico-chemical characterization of dihydrochalcones: Insight into the role of apple major flavonoids.

    Science.gov (United States)

    Gaucher, Matthieu; Dugé de Bernonville, Thomas; Lohou, David; Guyot, Sylvain; Guillemette, Thomas; Brisset, Marie-Noëlle; Dat, James F

    2013-06-01

    Flavonoids, like other metabolites synthesized via the phenylpropanoid pathway, possess a wide range of biological activities including functions in plant development and its interaction with the environment. Dihydrochalcones (mainly phloridzin, sieboldin, trilobatin, phloretin) represent the major flavonoid subgroup in apple green tissues. Although this class of phenolic compounds is found in very large amounts in some tissues (≈200mg/g of leaf DW), their physiological significance remains unclear. In the present study, we highlight their tissue-specific localization in young growing shoots suggesting a specific role in important physiological processes, most notably in response to biotic stress. Indeed, dihydrochalcones could constitute a basal defense, in particular phloretin which exhibits a strong broad-range bactericidal and fungicidal activity. Our results also indicate that sieboldin forms complexes with iron with strong affinity, reinforcing its antioxidant properties and conferring to this dihydrochalcone a potential for iron seclusion and/or storage. The importance of localization and biochemical properties of dihydrochalcones are discussed in view of the apple tree defense strategy against both biotic and abiotic stresses. Copyright © 2013 Elsevier Ltd. All rights reserved.

  4. Study of the radioprotective effect of flavonoid quercetin on human lymphocytes

    International Nuclear Information System (INIS)

    Siqueira, Williams Nascimento de

    2013-01-01

    Ionizing radiation has been used in various fields of study, as medicine, industry, energy production, surgical materials sterilization, preservation and sterilization of foods, among others. These radiations may be responsible for adverse effects at molecular level in living organisms, where most important damage occurs in deoxyribonucleic acid molecule, DNA. These harmful effects caused by radiation highlights the importance of acquiring knowledge about radioprotector substances because they can act as protector of living tissue of those effects. In this research was investigated the possible radioprotective effect 'in vitro' of the flavonoid quercetin in human lymphocytes exposed to gamma radiation. At first, test was performed to evaluate the antioxidant activity of quercetin by capturing DPPH free radical molecules. Then, it was collected peripheral blood of volunteers donors. Then the samples were irradiated from linear accelerator (Siemens Primus - energy of 6 MeV and dose rate of 200 cGy/min from IMIP-PE). After samples irradiation, lymphocytes were isolated from whole blood and then the culture was carried out to obtain lymphocyte in metaphases and subsequent, analysis of chromosomal abnormalities were done at optical microscope. Statistical analysis was used Student 't' test. The results showed that quercetin at a concentration of 37.5 μM presented radioprotective against damage from gamma radiation on human lymphocytes in vitro. Have been also observed that the irradiated lymphocytes showed morphologically unchanged after undergoing the presence of the flavonoid quercetin. (author)

  5. Total flavonoids content and biochemical screening of the leaves of tropical endemic medicinal plant Merremia borneensis

    Directory of Open Access Journals (Sweden)

    Muhammad Dawood Shah

    2014-12-01

    Full Text Available The developing and under developed countries mostly rely on traditional medicines. This herbal or traditional medicine involves the use of different types of organic extracts or the bioactive chemical constituents. This type of biochemical investigation provides health care at an affordable cost. This survey such as ethnomedicine keenly represents one of the best avenues in searching new economic plants for medicines. Keeping this view in mind, the present study is carried out in Merremia borneensis leaves of University Malaysia Sabah, Sabah, Malaysia. The plant has several beneficial properties, such as antioxidant activity. The dry powder of the leaves of M. borneensis was extracted with hexane, ethyl acetate, chloroform, butanol and aqueous ethanol. The flavonoids content of the extracts was determined by Willet method. The flavonoids content of the extracts as quercetin equivalents was found to be highest in aqueous ethanol (53.28% followed by chloroform (38.83%, ethyl acetate (24.51%, butanol (12.54% and hexane extract (3.44%. The results suggest the presence of phytochemical properties in the leaves, which are used in curing the ailments.

  6. Antimicrobial Activities of Three Medicinal Plants and Investigation of Flavonoids of Tripleurospermum disciforme.

    Science.gov (United States)

    Tofighi, Zahra; Molazem, Maryam; Doostdar, Behnaz; Taban, Parisa; Shahverdi, Ahmad Reza; Samadi, Nasrin; Yassa, Narguess

    2015-01-01

    Rosa damascena, Tripleurospermum disciforme and Securigera securidaca were used as disinfectant agents and for treatment of some disease in folk medicine of Iran. The antimicrobial effects of different fractions of seeds extract of S. securidaca, petals extract of R. damascena and aerial parts extract of T. disciforme were examined against some gram positive, gram negative and fungi by cup plate diffusion method. The petroleum ether and chloroform fractions of S. securidaca showed antibacterial activities against Staphylococcus aureus and Pseudomonas aeruginosa, while its methanol fraction had no antibacterial effects. R. damascena petals extract demonstrated antibacterial activities against Bacillus cereus, Staphylococcus epidermidis, S. aureus and Pseudomonas aeruginosa. T. disciforme aerial parts extract exhibited antimicrobial effects only against S. aureus and S. epidermidis. None of the fractions had any antifungal activities. Therefore, present study confirmed utility of these plants as disinfectant agents. Six flavonoids were isolated from T. disciforme: Luteolin, Quercetin-7-O-glucoside, Kaempferol, Kaempferol-7-O-glucoside, Apigenin and Apigenin-7-O-glucoside. The flavonoids and the antimicrobial activity of T. disciforme are reported for the first time.

  7. Flavonoid glycosides isolated from unique legume plant extracts as novel inhibitors of xanthine oxidase.

    Directory of Open Access Journals (Sweden)

    Chrysoula Spanou

    Full Text Available Legumes and the polyphenolic compounds present in them have gained a lot of interest due to their beneficial health implications. Dietary polyphenolic compounds, especially flavonoids, exert antioxidant properties and are potent inhibitors of xanthine oxidase (XO activity. XO is the main contributor of free radicals during exercise but it is also involved in pathogenesis of several diseases such as vascular disorders, cancer and gout. In order to discover new natural, dietary XO inhibitors, some polyphenolic fractions and pure compounds isolated from two legume plant extracts were tested for their effects on XO activity. The fractions isolated from both Vicia faba and Lotus edulis plant extracts were potent inhibitors of XO with IC(50 values range from 40-135 µg/mL and 55-260 µg/mL, respectively. All the pure polyphenolic compounds inhibited XO and their K(i values ranged from 13-767 µM. Ten of the compounds followed the non competitive inhibitory model whereas one of them was a competitive inhibitor. These findings indicate that flavonoid isolates from legume plant extracts are novel, natural XO inhibitors. Their mode of action is under investigation in order to examine their potential in drug design for diseases related to overwhelming XO action.

  8. Apple Flavonoids Suppress Carcinogen-Induced DNA Damage in Normal Human Bronchial Epithelial Cells

    Directory of Open Access Journals (Sweden)

    Vazhappilly Cijo George

    2017-01-01

    Full Text Available Scope. Human neoplastic transformation due to DNA damage poses an increasing global healthcare concern. Maintaining genomic integrity is crucial for avoiding tumor initiation and progression. The present study aimed to investigate the efficacy of an apple flavonoid fraction (AF4 against various carcinogen-induced toxicity in normal human bronchial epithelial cells and its mechanism of DNA damage response and repair processes. Methods and Results. AF4-pretreated cells were exposed to nicotine-derived nitrosamine ketones (NNK, NNK acetate (NNK-Ae, methotrexate (MTX, and cisplatin to validate cytotoxicity, total reactive oxygen species, intracellular antioxidants, DNA fragmentation, and DNA tail damage. Furthermore, phosphorylated histone (γ-H2AX and proteins involved in DNA damage (ATM/ATR, Chk1, Chk2, and p53 and repair (DNA-PKcs and Ku80 mechanisms were evaluated by immunofluorescence and western blotting, respectively. The results revealed that AF4-pretreated cells showed lower cytotoxicity, total ROS generation, and DNA fragmentation along with consequent inhibition of DNA tail moment. An increased level of γ-H2AX and DNA damage proteins was observed in carcinogen-treated cells and that was significantly (p≤0.05 inhibited in AF4-pretreated cells, in an ATR-dependent manner. AF4 pretreatment also facilitated the phosphorylation of DNA-PKcs and thus initiation of repair mechanisms. Conclusion. Apple flavonoids can protect in vitro oxidative DNA damage and facilitate repair mechanisms.

  9. 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.

  10. 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.

  11. 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)

  12. 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...

  13. 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.

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

    Science.gov (United States)

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

    1999-01-01

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

  15. Study on the high flavonoids mutants of tartarian buckwheat by radiation induced

    International Nuclear Information System (INIS)

    Li Guozhu; Shen Huifang

    2011-01-01

    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)

  16. 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

  17. 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.

  18. Quantitative modeling of flavonoid glycosides isolated from Paliurus spina-christi Mill.

    OpenAIRE

    Medić-Šarić, Marica; Maleš, Željan; Šarić, Slavko; Brantner, Adelheid

    1996-01-01

    Several QSPR models for predicting the properties of flavonoid glycosides isolated from Paliurus spina-christi Mill, and of some related flavonoids were described and evaluated. Log P values for all of them were calculated according to the method of Rekker. All investigated flavonoids showed expressive hydrophobicity. Significant correlation between the partition coefficient, log P, and van der Waals volume, Vw (calculated according to the method described by Moriguchi et al.) was obtained. T...

  19. Intrauterine application of flavonoids in puerperal dairy cows: reproductive tract involution and fertility at high-altitude environments

    Directory of Open Access Journals (Sweden)

    Gutierrez-Reinoso MA

    2016-12-01

    Full Text Available The main objective of the present study was to evaluate the effects of postpartum intrauterine administration of flavonoids in order to hasten reproductive tract involution and to shorten the parturition-to-conception interval in dairy cows. A total of 40 Holstein cows (2nd-3rd lactation; BC: 3-3.5 were divided randomly into 4 groups [1 control group (T1 and 3 treatment groups (T2, T3 and T4]. Treatments consisted of one single intrauterine administration on day 10 postpartum of 90 mg (T2, 180 mg (T3 and 360 mg (T4 of ultrapure flavonoids (20 ml. Ultrasonographic measurements of different reproductive tract anatomical structures were scored from cervix (length, width and thickness, uterus (diameter and thickness and ovaries (length and width during the postpartum period (day 10, 15 and 21 postpartum. As fertility parameters rate of return to estrus, pregnancy rate and calving-to-conception interval were scored as well. Pregnancy status was performed using ultrasonography (day 35 post-insemination. There were multiple differences (p 0.05 in ovarian dimensions from T1, T2, T3 and T4 groups during the postpartum period after ultrasonographic analysis at day 10, 15 and 21. Return to estrus index, pregnancy rate and calving-to-conception interval differed between T1 and T2-T3-T4 groups (p 0.05. In conclusion, intrauterine application of flavonoids enhanced the cervical and uterine involution. Finally, although no significant differences among treatments, theintrauterine application of flavonoids improved the return to estrus index, pregnancy rate and calving-to-conception interval compared with non-treated dairy cows.

  20. Effect of the ionizing radiation and aging time on total flavonoids contents in Brazilian sugarcane spirit composed with green propolis

    International Nuclear Information System (INIS)

    Baptista, Antonio S.; Alencar, Severino M. de; Tiveron, Ana P.; Prado, Adna; Bergamaschi, Keityane B.; Veiga, Lucimara F. da; Aguiar, Claudio L. de; Baptista, Aparecido S.; Horii, Jorge

    2009-01-01

    Propolis is a natural product from vegetable origin, but, this substance, in general, is collected in the beehives. This product is largely known because its heath benefit attributed to its biological properties. On the other hand, Brazilian sugarcane spirit, 'cachaca', is an interesting alcoholic beverage with an increasing importance in the segment in many markets in the world. Therefore, was evaluating the addition of the propolis into cachaca and the effect of ionizing radiation on propolis compounds with biological properties. Samples of cachaca with propolis used in irradiation experiments were prepared from cachaca (40 deg GL) composed with propolis (0.1%). Eight treatments, with four repetitions each, were considered in this study. Three doses of ionizing energy from electron beam and gamma radiation from 60 Co were applied on the cachaca samples, i.e. 0.5, 1.0, and 2.0 kGy, with the goal to accelerate the aging time of the cachaca. The sugarcane spirits samples were storage during two periods (immediately after the radiation treatment and 30 months after the treatments) and their flavonoids contents were analyzed. Flavonoids contents in sugarcane spirit were statistically different between both storage time. The samples of cachaca treated with electron beam at 2.0 kGy presented the highest reduction in flavonoids contents, approximately 30.0 % in relation to the first analysis time. In conclusion, the time of storage to promote reduction on the flavonoids contents and the ionizing radiation also promoted reduction on the contents of these compounds, mainly in the first period of storage. (author)