Antioxidant and prooxidant properties of flavonoids
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Winkel-Shirley, 2001, Flavonoid biosynthesis: a colorful model for genetics, biochemistry, cell biology and biotechnology, Plant Physiol, 126, 485, 10.1104/pp.126.2.485
Formica, 1995, Review of the biology of quercetin and related bioflavonoids, Food Chem Toxicol, 33, 1061, 10.1016/0278-6915(95)00077-1
de Lange, 2007, Polyphenolic grape extract inhibits platelet activation through PECAM-1: an explanation for the French paradox, Alcohol Clin Exp Res, 31, 1308, 10.1111/j.1530-0277.2007.00439.x
Rosenkranz, 2002, Inhibition of the PDGF receptor by red wine flavonoids provides a molecular explanation for the “French paradox”, FASEB J, 16, 1958, 10.1096/fj.02-0207fje
Weber, 2003, Inhibition of adenovirus infection and adenain by green tea catechins, Antivir. Res., 58, 167, 10.1016/S0166-3542(02)00212-7
Alvesalo, 2006, Inhibitory effect of dietary phenolic compounds on Chlamydia pneumoniae in cell cultures, Biochem Pharmacol, 71, 735, 10.1016/j.bcp.2005.12.006
Subarnas, 2000, Analgesic and anti-inflammatory activity of the proanthocyanidins shellegueain A from Polypodium feei, Phytomedicine, 7, 401, 10.1016/S0944-7113(00)80061-6
Widlansky, 2005, Effects of black tea consumption on plasma catechins and markers of oxidative stress and inflammation in patients with coronary artery disease, Free Radic Biol Med, 38, 499, 10.1016/j.freeradbiomed.2004.11.013
Calderone, 2004, Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels, Naunyn-Schmiedebergs Arch Pharmacol, 370, 290, 10.1007/s00210-004-0964-z
Rump, 1995, Effects of different inotropes with antioxidant properties on acute regional myocardial ischemia in isolated rabbit hearts, Gen Pharmacol, 26, 603, 10.1016/0306-3623(94)00209-6
Duthie, 2000, Plant polyphenols in cancer and heart disease: implications as nutritional antioxidants, Nutr Res Rev, 13, 79, 10.1079/095442200108729016
Mladěnka, 2010, Cardiovascular effects of flavonoids are not caused only by direct antioxidant activity, Free Radic Biol Med, 15, 963, 10.1016/j.freeradbiomed.2010.06.010
Cirico, 2006, Additive or synergetic effects of phenolic compounds on human low density lipoprotein oxidation, Food Chem Toxicol, 44, 510, 10.1016/j.fct.2005.08.025
Hubbard, 2004, Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans, J Thromb Haemost, 2, 2138, 10.1111/j.1538-7836.2004.01067.x
Valensi, 1996, Effects of a purified micronized flavonoid fraction on capillary filtration in diabetic patients, Diabet Med, 13, 882, 10.1002/(SICI)1096-9136(199610)13:10<882::AID-DIA247>3.0.CO;2-4
Halliwell, 1998
Lachman, 2007, Comparison of the total antioxidant status of Bohemian wines during the wine-making process, Food Chem, 103, 802, 10.1016/j.foodchem.2006.09.024
Lachman, 2009, Antioxidants and antioxidant activity of red and white wines affected by winemaking and other extrinsic and intrinsic factors, 91
Renaud, 1992, Wine, alcohol, platelets, and the French paradox for coronary heart disease, Lancet, 339, 1523, 10.1016/0140-6736(92)91277-F
Rice-Evans, 1995, Antioxidants — the case for fruit and vegetables in the diet, Br Food J, 97, 35, 10.1108/00070709510100163
Hertog, 1993, Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study, Lancet, 342, 1007, 10.1016/0140-6736(93)92876-U
Hertog, 1997, Antioxidant flavonols and coronary heart disease risk, Lancet, 349, 699, 10.1016/S0140-6736(05)60135-3
Prior, 2000, Antioxidant phytochemicals in fruits and vegetables: diet and health implications, Hortic. Sci., 35, 588
Frei, 2003, Antioxidant activity of tea polyphenols in vivo: evidence from animal studies, J Nutr, 133, S3275, 10.1093/jn/133.10.3275S
Jovanovic, 1996, Reduction potentials of flavonoid and model peroxyl radicals. Which ring in flavonoids is responsible for antioxidant activity?, J Chem Soc Perkins Trans, 2, 2497, 10.1039/p29960002497
Jovanovic, 1997, Antioxidant potential of theaflavins. A pulse radiolysis study, J Am Chem Soc, 119, 5337, 10.1021/ja970120f
Maeta, 2007, Green tea polyphenols fuction as prooxidants to active oxidative-stress-responsive transcription factors in yeasts, Appl. Environ. Microbiol., 73, 572, 10.1128/AEM.01963-06
Nijveldt, 2001, Flavonoids: a review of probable mechanisms of action and potential applications, Am J Clin Nutr, 74, 418, 10.1093/ajcn/74.4.418
Ferrali, 1997, Protection against oxidative damage of erythrocyte membranes by the flavonoid quercetin and its relation to iron chelating activity, FEBS Lett, 416, 123, 10.1016/S0014-5793(97)01182-4
Hirano, 2001, Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation, J Nutr Sci Vitaminol (Tokyo), 47, 357, 10.3177/jnsv.47.357
Heim, 2002, Flavonoid antioxidants: chemistry, metabolism and structure–activity relationships, J Nutr Biochem, 13, 572, 10.1016/S0955-2863(02)00208-5
Cos, 1998, Structure–activity relationship and classification of flavonoids as inhibitors of xantine oxidase and superoxide scavengers, J Nat Prod, 61, 71, 10.1021/np970237h
van Acker, 1995, Flavonoids as scavengers of nitric oxide radical, Biochem Biophys Res Commun, 214, 755, 10.1006/bbrc.1995.2350
Lotito, 2006, Consumption of flavonoid-rich foods and increased plasma antioxidant capacity in humans: cause, consequence, or epiphenomenon?, Free Radic Biol Med, 41, 1727, 10.1016/j.freeradbiomed.2006.04.033
Yeh, 2005, Pro-oxidative effect of β-carotene and the interaction with flavonoids on UVA-induced DNA strand breaks in mouse fibroblast C3H10T1/2 cells, J Nutr Biochem, 16, 729, 10.1016/j.jnutbio.2005.03.012
Burda, 2001, Antioxidant and antiradical activities of flavonoids, J Agric Food Chem, 49, 2774, 10.1021/jf001413m
Taubert, 2003, Reaction rate constants of superoxide scavenging by plant antioxidants, Free Radic Biol Med, 35, 1599, 10.1016/j.freeradbiomed.2003.09.005
Amić, 2007, SAR and QSAR of the antioxidant activity of flavonoids, Curr Med Chem, 14, 827, 10.2174/092986707780090954
Lotito, 2000, Influence of oligomer chain length on the antioxidant activity of procyanidins, Biochem Biophys Res Commun, 276, 945, 10.1006/bbrc.2000.3571
Rice-Evans, 1996, Structure–antioxidant activity relationships of flavonoids and phenolic acids, Free Radic Biol Med, 20, 933, 10.1016/0891-5849(95)02227-9
Amić, 2010, Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids, Bioorg Med Chem, 18, 28, 10.1016/j.bmc.2009.11.015
Cavia-Saiz, 2010, Antioxidant properties, radical scavenging activity and biomolecule protection capacity of flavonoid naringenin and its glycoside naringin: a comparative study, J Sci Food Agric, 90, 1238, 10.1002/jsfa.3959
Khknen, 2003, Antioxidant activity of anthocyanins and their aglycons, J Agric Food Chem, 51, 628, 10.1021/jf025551i
Mishra, 2003, Effect of O-glycosilation on the antioxidant activity and free radical reactions of a plant flavonoid, chrysoeriol, Bioorg Med Chem, 11, 2677, 10.1016/S0968-0896(03)00232-3
Sun, 2010, On-line HPLC method for screening of antioxidants against superoxide anion radical from complex mixtures, J Sep Sci, 33, 1018, 10.1002/jssc.200900588
Firuzi, 2004, Hypochlorite scavenging activity of flavonoids, J Pharm Pharmacol, 56, 801, 10.1211/0022357023556
Firuzi, 2005, Evaluation of the antioxidant activity of flavonoids by “ferric reducing antioxidant power” assay and cyclic voltammetry, Biochim Biophys Acta, 1721, 174, 10.1016/j.bbagen.2004.11.001
Bors, 1990, Flavonoids as antioxidants: determination of radical-scavenging efficiencies, Methods Enzymol, 186, 343, 10.1016/0076-6879(90)86128-I
Croft, 2006, The chemistry and biological effects of flavonoids and phenolic acids, Ann NY Acad Sci, 854, 435, 10.1111/j.1749-6632.1998.tb09922.x
Zhu, 2001, Functional characterization of transcription regulators that interact with the electrophile response element, Biochem Biophys Res Commun, 23, 212, 10.1006/bbrc.2001.5944
Nerland, 2007, The antioxidant/electrophile response element motif, Drug Metab Rev, 39, 235, 10.1080/03602530601125000
Lee-Hilz, 2006, Pro-oxidant activity of flavonoids induces EpRE-mediated gene expression, Chem Res Toxicol, 19, 1499, 10.1021/tx060157q
Nagata, 1999, Antioxidative action of flavonoids, quercetin and catechin, mediated by the activation of glutathione peroxidise, Tokai J Exp Clin Med, 24, 1
Martín, 2010, Cocoa flavonoids up-regulate antioxidant enzyme activity via the ERK1/2 pathway to protect against oxidative stress-induced apoptosis in HepG2 cells, J Nutr Biochem, 21, 196, 10.1016/j.jnutbio.2008.10.009
Leung, 2006, Antioxidant enzymes activity involvement in luteolin-induced human lung squamous carcinoma CH27 cell apoptosis, Eur J Pharmacol, 534, 12, 10.1016/j.ejphar.2006.01.021
Kaviarasan, 2008, Antioxidant efficacy of flavonoid-rich fraction from Spermacoce hispida in hyperlipidemic rats, J Appl Biomed, 6, 165, 10.32725/jab.2008.020
Jung, 2003, Naringin supplementation lowers plasma lipids and enhances erytrocyte antioxidant enzyme activities in hypercholesterolemic subjects, Clin Nutr, 22, 561, 10.1016/S0261-5614(03)00059-1
Breinholt, 1999, Differential effects of dietary flavonoids on drug metabolizing and antioxidant enzymes in female rat, Xenobiotica, 29, 1227, 10.1080/004982599237903
Brown, 1998, Structural dependence of flavonoid interactions with Cu2+ ions: implications for their antioxidant properties, Biochem J, 330, 1173, 10.1042/bj3301173
Kopacz, 2003, Complexes of cadmium(II), mercury(II) and lead(II) with quercetin-5′-sulfonic acid (QSA), Pol J Chem, 77, 1777
Szeląg, 2003, Assessment of efficacy of quercetin-5′-sulfonic acid sodium salt in the treatment of acute chromium poisoning: experimental studies, Pol J Pharmacol, 55, 1097
Chlebda, 2010, Influence of water-soluble flavonoids, quercetin-5′-sulfonic acid sodium salt and morin-5′-sulfonic acid sodium salt, on antioxidant parameters in the subacute cadmium intoxication mouse model, Exp Toxicol Pathol, 62, 105, 10.1016/j.etp.2009.02.118
Zhu, 2000, Interaction between flavonoids and α-tocopherol in human low density lipoprotein, J Nutr Biochem, 11, 14, 10.1016/S0955-2863(99)00065-0
Mukai, 2005, Structure–activity relationship of tocopherol-regeneration reaction by catechin, Free Radic Biol Med, 38, 1243, 10.1016/j.freeradbiomed.2005.01.011
Zhu, 1999, Regeneration of alpha-tocopherol in human low-density lipoprotein by green tea catechins, J Agric Food Chem, 47, 2020, 10.1021/jf9809941
Hanasaki, 1994, The correlation between active oxygens scavenging and antioxidative effects of flavonoids, Free Radic Biol Med, 16, 845, 10.1016/0891-5849(94)90202-X
Ursini, 1994, A novel antioxidant flavonoid (IdB 1031) affecting molecular mechanisms of cellular activation, Free Radic Biol Med, 16, 547, 10.1016/0891-5849(94)90054-X
Shoskes, 1998, Effect of bioflavonoids quercetin and curcumin on ischemic renal injury: a new class of renoprotective agents, Transplantation, 66, 147, 10.1097/00007890-199807270-00001
Chang, 1993, Inhibitory effects of flavonoids on xanthine oxidase, Anticancer Res, 13, 2165
Iio, 1986, Effects of flavonoids on xanthine oxidation as well as on cytochrome c reduction by milk xanthine oxidase, J Nutr Sci Vitaminol (Tokyo), 32, 635, 10.3177/jnsv.32.635
Korkina, 1997, Antioxidant and chelating properties of flavonoids, Adv Pharmacol, 38, 151, 10.1016/S1054-3589(08)60983-7
Umeki, 1994, Mechanisms for the activation/elektron transfer of neurophil NADPH-oxidase complex and molecular patology of chronic granulomatous disease, Ann Hematol, 68, 267, 10.1007/BF01695032
Ago, 2003, Phosphorylation of p47phox directs phox homology domain from SH3 domain toward phosphoinositides, leading to phagocyte NADPH oxidase activation, Proc Natl Acad Sci USA, 100, 4474, 10.1073/pnas.0735712100
Ferriola, 1989, Protein kinase C inhibition by plant flavonoids: kinetic mechanisms and structure–activity relationships, Biochem Pharmacol, 38, 1617, 10.1016/0006-2952(89)90309-2
Huk, 1998, Bioflavonoid quercetin scavenges superoxide and increases nitric oxide concentration in ischaemia–reperfusion injury: an experimental study, Br J Surg, 85, 1080, 10.1046/j.1365-2168.1998.00787.x
Rubbo, 1994, Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation, J Biol Chem, 269, 26066, 10.1016/S0021-9258(18)47160-8
Matsuda, 2003, Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action, Bioorg Med Chem, 11, 1995, 10.1016/S0968-0896(03)00067-1
Olszanecki, 2002, Flavonoids and nitric oxidesynthase, J Physiol Pharmacol, 53, 571
Kim, 1999, Effects of naturally occurring flavonoids on nitric oxide production in the macrophage cell line RAW 264.7 and their structure–activity relationships, Biochem Pharmacol, 58, 759, 10.1016/S0006-2952(99)00160-4
Kim, 2005, Down-regulatory effect of quercetrin gallate on nuclear factor kappaB-dependent inducible nitric oxide synthase expression in lipopolysaccharide-stimulated macrophages RAW 264.7, Biochem Pharmacol, 69, 1577, 10.1016/j.bcp.2005.03.014
Cao, 1997, Antioxidant and prooxidant behavior of flavonoids: structure–activity relationships, Free Radic Biol Med, 22, 749, 10.1016/S0891-5849(96)00351-6
Haenen, 1997, Peroxynitrite scavenging by flavonoids, Biochem Biophys Res Commun, 236, 591, 10.1006/bbrc.1997.7016
Choi, 2002, The structure–activity relationship of flavonoids as scavengers of peroxynitrite, Phytother Res, 16, 232, 10.1002/ptr.828
Cao, 1998, Serum antioxidant capacity is increased by consumption of strawberries, spinach, red wine or vitamin C in elderly women, J Nutr, 128, 2383, 10.1093/jn/128.12.2383
Day, 1995, Cardioprotective effect of red wine may be mediated by urate, Clin Chem, 41, 1319, 10.1093/clinchem/41.9.1319
Maxwell, 2000, Impact of red wine on antioxidant status in vivo, Eur Heart J, 21, 1482
Natella, 2002, Coffee drinking influences plasma antioxidant capacity in humans, J Agric Food Chem, 50, 6211, 10.1021/jf025768c
Halliwell, 2007, 282, 93
Obermüller-Jevic, 1999, Enhancement of the UVA induction of haem oxygenase-1 expression by beta-carotene in human skin fibroblasts, FEBS Lett, 460, 212, 10.1016/S0014-5793(99)01342-3
Offord, 2002, Photoprotective potential of lycopene, beta-carotene, vitamin E, vitamin C and carnosic acid in UVA-irradiated human skin fibroblasts, Free Radic Biol Med, 32, 1293, 10.1016/S0891-5849(02)00831-6
Rice-Evans, 1995, The relative antioxidant activities of plant-derived polyphenolic flavonoids, Free Radical Res, 22, 375, 10.3109/10715769509145649
Williams, 2004, Flavonoids: antioxidants or signalling molecules?, Free Radic Biol Med, 36, 838, 10.1016/j.freeradbiomed.2004.01.001
Spencer, 2007, The interactions of flavonoids within neuronal signalling pathways, Genes Nutr., 2, 257, 10.1007/s12263-007-0056-z
Hollman, 1998, Bioavailability and health effects of dietary flavonols in man, Arch Toxicol Suppl, 20, 237, 10.1007/978-3-642-46856-8_21
Spencer, 2001, Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts, Free Radic Biol Med, 31, 1139, 10.1016/S0891-5849(01)00704-3
Spencer, 2003, Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites, Biochem J, 372, 173, 10.1042/bj20021972
Breinholt, 2002, In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids, Food Chem Toxicol, 40, 609, 10.1016/S0278-6915(01)00125-9
Pollard, 2006, The reaction of flavonoid metabolites with peroxynitrite, Biochem Biophys Res Commun, 350, 960, 10.1016/j.bbrc.2006.09.131
Spencer, 2003, Metabolism of tea flavonoids in the gastrointestinal tract, J Nutr, 133, 3255S, 10.1093/jn/133.10.3255S
Piskula, 1998, Accumulation of (−)-epicatechin metabolites in rat plasma after oral administration and distribution of conjugation enzymes in rat tissues, J Nutr, 128, 1172, 10.1093/jn/128.7.1172
Dueñas, 2010, Antioxidant evaluation of O-methylated metabolites of catechin, epicatechin and quercetin, J Pharm Biomed Anal, 51, 443, 10.1016/j.jpba.2009.04.007
Lemańska, 2004, The effect of catechol O-methylation on radical scavenging characteristics of quercetin and luteolin — a mechanistic insight, Free Radic Res, 38, 639, 10.1080/10715760410001694062
Metodiewa, 1999, Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product, Free Radic Biol Med, 26, 107, 10.1016/S0891-5849(98)00167-1
Kessler, 2003, Anti- and pro-oxidant activity of rutin and quercetin derivatives, J Pharm Pharmacol, 55, 131, 10.1211/002235702559
Facino, 1999, Diet enriched with procyanidins enhances antioxidant activity and reduces myocardial post-ischaemic damage in rats, Life Sci, 64, 627, 10.1016/S0024-3205(98)00605-5
Liu, 2010, The antioxidant activity and hypolipidemic activity of the total flavonoids from the fruit of Rosa laevigata Michx, Nat Sci, 3, 175
Spencer, 2003, Intracellular metabolism and bioactivity of quercetin and its in vivo metabolites, Biochem J, 372, 173, 10.1042/bj20021972
Terao, 1999, Dietary flavonoids as antioxidants in vivo: conjugated metabolites of (−)-epicatechin and quercetin participate in antioxidative defence in blood plasma, J Med Invest, 46, 159
Santos, 2008, Influence of the metabolic profile on the in vivo antioxidant activity of quercetin under a low dosage oral regimen in rats, Br J Pharmacol, 153, 1750, 10.1038/bjp.2008.46
Justino, 2004, Plasma quercetin metabolites: structure−antioxidant activity relationships, Arch Biochem Biophys, 432, 109, 10.1016/j.abb.2004.09.007
Mellor, 2010, High-cocoa polyphenol-rich chocolate improves HDL cholesterol in Type 2 diabetes patients, Diabet Med, 27, 1318, 10.1111/j.1464-5491.2010.03108.x
Boyle, 2000, Absorption and DNA protective effects of flavonoid glycosides from an onion meal, Eur J Nutr, 39, 213, 10.1007/s003940070014
Fukushima, 2009, Coffee and green tea as a large source of antioxidant polyphenols in the Japanese population, J Agric Food Chem, 57, 1253, 10.1021/jf802418j
Guo, 2008, Pomegranate juice is potentially better than apple juice in improving antioxidant function in elderly subjects, Nutr Res, 28, 72, 10.1016/j.nutres.2007.12.001
Halliwell, 2008, Are polyphenols antioxidants or pro-oxidants? What do we learn from cell culture and in vivo studies?, Arch Biochem Biophys, 476, 107, 10.1016/j.abb.2008.01.028
Hodnick, 1986, Inhibition of mitochondrial respiration and production of toxic oxygen radicals by flavonoids: structure activity study, Biochem Pharmacol, 35, 2345, 10.1016/0006-2952(86)90461-2
Galey, 1997, Potential use of iron chelators against oxidative damage, Adv Pharmacol, 38, 167, 10.1016/S1054-3589(08)60984-9
Arakawa, 2004, Role of hydrogen peroxide in bactericidal action of catechin, Biol Pharm Bull, 27, 277, 10.1248/bpb.27.277
Nakagawa, 2004, Generation of hydroxide peroxide primarily contributes to the induction of Fe(II)-dependent apoptosis in Jurkat cells by (−)-epigallocatechin-3-gallate, Carcinogenesis, 25, 1567, 10.1093/carcin/bgh168
Stadler, 2004, Direct detection and quantification of transition metal ions in human atherosclerotic plaques: evidence for the presence of elevated levels of iron and copper, Arterioscler Thromb Vasc Biol, 24, 949, 10.1161/01.ATV.0000124892.90999.cb
Yen, 2003, Pro-oxidative properties of flavonoids in human lymphocytes, Biosci Biotechnol Biochem, 67, 1215, 10.1271/bbb.67.1215
Laughton, 1989, Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin: effects of lipid peroxidation, hydroxyl radical generation and bleomycin-dependent damage to DNA, Biochem Pharmacol, 38, 2859, 10.1016/0006-2952(89)90442-5
Wilms, 2008, Discriminative protection against hydroxyl and superoxide anion radicals by quercetin in human leucocytes in vitro, Toxicol In Vitro, 22, 301, 10.1016/j.tiv.2007.09.002
Halliwell, 1989
Cadenas, 1995, Mechanisms of oxygen activation and reactive oxygen species detoxification, 1
Hernández, 2009, How relevant are flavonoids as antioxidants in plants?, Trends Plant Sci, 14, 125, 10.1016/j.tplants.2008.12.003
Bayrakçeken, 2003, High resolution electronic absorption spectra of anisole and phenoxyl radical, Spectrochim Acta, 59, 135, 10.1016/S1386-1425(02)00143-9
Awad, 2002, The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent, Chem Res Toxicol, 15, 343, 10.1021/tx010132l
Torres, 2005, Conjugation of catechins with cysteine generates antioxidant compounds with enhanced neuroprotective activity, Phytochemistry, 66, 2032, 10.1016/j.phytochem.2004.12.003
Kanakis, 2005, DNA interaction with naturally occurring antioxidant flavonoids quercetin, kaempferol, and delphinidin, J Biomol Struct Dyn, 22, 719, 10.1080/07391102.2005.10507038
McCord, 1995, Superoxide radical: controversies, contradictions, and paradoxes, Proc Soc Exp Biol Med, 209, 112, 10.3181/00379727-209-43885C
Galati, 1999, Glutathione-dependent generation of reactive oxygen species by the peroxidase-catalyzed redox cycling of flavonoids, Chem Res Toxicol, 12, 521, 10.1021/tx980271b
Chan, 1999, Oxygen activation during peroxidase catalysed metabolism of flavones or flavanones, Chem Biol Interact, 122, 15, 10.1016/S0009-2797(99)00103-9
Galati, 2002, Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics, Toxicology, 177, 91, 10.1016/S0300-483X(02)00198-1
Canada, 1990, The production of reactive oxygen species by dietary flavonols, Free Radic Biol Med, 9, 441, 10.1016/0891-5849(90)90022-B
El Hajji, 2006, Interactions of quercetin with iron and copper ions: complexation and autoxidation, Free Radic Res, 40, 303, 10.1080/10715760500484351
Hodnick, 1989, The production of hydroxyl and semiquinone free radicals during the autoxidation of redox active flavonoids, 149
Hodnick, 1994, Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids, Biochem Pharmacol, 47, 573, 10.1016/0006-2952(94)90190-2
Buss, 2005, The action of quercetin on the mitochondrial NADH to NAD(+) ratio in the isolated perfused rat liver, Planta Med, 71, 1118, 10.1055/s-2005-873174
R.P. Constantin, J. Constantin, C.L. Pagadigorria, E.L. Ishii-Iwamoto, A. Bracht, C.V. Castro, N.S. Yamamoto, Prooxidant activity of fisetin: effects on energy metabolism in the rat liver, J. Biochem. Mol. Toxicol. DOI: 10.1002/jbt.20367.
Goldman, 1999, Myeloperoxidase-catalyzed redox-cycling of phenol promotes lipid peroxidation and thiol oxidation in HL-60 cells, Free Radical Biol Med, 27, 1050, 10.1016/S0891-5849(99)00140-9
Bast, 1991, Oxidants and antioxidants: state of the art, Am J Med, 91, 2S, 10.1016/0002-9343(91)90278-6
Meister, 1994, Glutathione–ascorbic acid antioxidant system in animals, J Biol Chem, 269, 9397, 10.1016/S0021-9258(17)36891-6
Boots, 2003, Oxidized quercetin reacts with thiols rather than with ascorbate: implication for quercetin supplementation, Biochem Biophys Res Commun, 308, 560, 10.1016/S0006-291X(03)01438-4
Dai, 2008, Antioxidant synergism of green tea polyphenols with α-tocopherol and l-ascorbic acid in SDS micelles, Biochimie, 90, 1499, 10.1016/j.biochi.2008.05.007
Sahu, 1996, Pro-oxidant activity of flavonoids: effects on glutathione and glutathione S-transferase in isolated rat liver nuclei, Cancer Lett, 104, 193, 10.1016/0304-3835(96)04251-6
Reboul, 2007, Effect of the main dietary antioxidants (carotenoids, γ-tocopherol, polyphenols, and vitamin C) on α-tocopherol absorption, Eur J Clin Nutr, 61, 1167, 10.1038/sj.ejcn.1602635
Ohshima, 1998, Antioxidant and pro-oxidant actions of flavonoids: effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxyl anion, Free Radic Biol Med, 25, 1057, 10.1016/S0891-5849(98)00141-5
Yamashita, 1999, Mechanism of oxidative DNA damage induced by quercetin in the presence of Cu(II), Mutat Res, 425, 107, 10.1016/S0027-5107(99)00029-9