The pro-oxidant chemistry of the natural antioxidants vitamin C, vitamin E, carotenoids and flavonoids

Environmental Toxicology and Pharmacology - Tập 11 Số 3-4 - Trang 321-333 - 2002
Ivonne M.C.M. Rietjens1,2, Marelle G. Boersma1, Laura de Haan1, Bert Spenkelink1, Hanem M. Awad1, Nicole H.P. Cnubben3,2, Jelmer J. van Zanden1,2, Hester van der Woude1,2, G.M. Alink1,2, J.H. Koeman1
1Division of Toxicology, Wageningen University, Tuinlaan 5, 6703 HE Wageningen, The Netherlands
2WU/TNO Center for Food Toxicology, P.O. Box 8000, 6700 EA Wageningen, The Netherlands
3TNO Nutrition and Food Research, P.O. Box 360, 3700 AJ Zeist, The Netherlands

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Agullo, 1997, Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: a comparison with tyrosine kinase and protein kinase C inhibition, Biochem. Pharmacol., 53, 1649, 10.1016/S0006-2952(97)82453-7

Avila, 1994, Quercetin mediates the down-regulation of mutant p53 in the human breast cancer cell line MDA-MB468, Cancer Res., 54, 2424

Awad, 2000, Peroxidase-catalysed formation of quercetin-quinone methide glutathione adducts, Arch. Biochem. Biophys., 378, 224, 10.1006/abbi.2000.1832

Awad, 2001, Structure activity study on the quinone/quinone methide chemistry of flavonoids, Chem. Res. Toxicol., 14, 398, 10.1021/tx000216e

Bandera, 1997, Diet and alcohol consumption and lung cancer risk in the New York State Cohort (United States), Cancer Causes Control, 8, 828, 10.1023/A:1018456127018

Block, 1992, Fruit, vegetables and cancer prevention: a review of the epidemiological evidence, Nutr. Cancer, 18, 1, 10.1080/01635589209514201

Boersma, 2000, Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide, Chem. Res. Toxicol., 13, 185, 10.1021/tx990161k

Bolton, 1998, Role of quinoids in estrogen carcinogenesis, Chem. Res. Toxicol., 11, 1113, 10.1021/tx9801007

Bolton, 2000, Role of quinones in Toxicology, Chem. Res. Toxicol., 13, 135, 10.1021/tx9902082

Brown, 1980, A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds, Mut. Res., 75, 243, 10.1016/0165-1110(80)90029-9

Brown, 1998, Luteolin-rich artichoke extract protects low density lipoprotein from oxidation in vitro, Free Rad. Res., 29, 247, 10.1080/10715769800300281

Cao, 1997, Antioxidant and prooxidant behavior of flavonoids: structure–activity relationships, Free Rad. Biol. Med., 22, 749, 10.1016/S0891-5849(96)00351-6

Comstock, 1997, The risk of developing lung cancer associated with antioxidants in the blood: ascorbic acid, carotenoids, alpha-tocopherol, selenium and total peroxyl radical absorbing capacity, Cancer Epidemiol. Biomarkers Prev., 6, 907

Diplock, 1996, The Leon Goldberg memorial lecture: antioxidants and disease prevention, Food Chem. Toxicol., 34, 1013, 10.1016/S0278-6915(96)00053-1

Diplock, 1998, Functional food science and defence against reactive oxidative species, Br. J. Nutr., 80, S77, 10.1079/BJN19980106

Deschner, 1991, Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia, Carcinogenesis, 12, 1193, 10.1093/carcin/12.7.1193

Dunnick, 1992, Toxicity and carcinogenicity studies of quercetin, a natural component of foods, Fundam. Appl. Toxicol., 19, 423, 10.1016/0272-0590(92)90181-G

Ertürk, 1985, Bracken ferns carcinogens and quercetin, Fed. Proc., 44, 2344

Flagg, 1995, Epidemiologic studies of antioxidants and cancer in humans, J. Am. Coll. Nutr., 14, 419, 10.1080/07315724.1995.10718532

Frémont, 1998, Dietary flavonoids reduce lipid peroxidation in rats fed polyunsaturated or monounsaturated fat diets, J. Nutr., 128, 1495, 10.1093/jn/128.9.1495

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

Galati, 2001, Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation, Free Rad. Biol. Med., 30, 370, 10.1016/S0891-5849(00)00481-0

Halliwell, 1990, How to characterize a biological antioxidant, Free Rad. Res. Commun., 9, 1, 10.3109/10715769009148569

Halliwell, 1987, Biologically significant scavenging of the myeloperoxidase-derived oxidant hypochlorus acid by ascorbic acid, FEBS Lett., 213, 15, 10.1016/0014-5793(87)81456-4

Hatchcock, J.N., 1997. Vitamin and Minerals safety. Council for responsible nutrition, Washington, DC (www.crnusa.org).

Henderson, 1998, Increased skin tumorigenesis in mice lacking pi-class glutathione-S-transferases, Proc. Natl. Acad. Sci. USA, 95, 5275, 10.1073/pnas.95.9.5275

Higson, 1988, Iron enhancement of ascorbate toxicity, Free Rad. Res. Commun., 5, 107, 10.3109/10715768809066918

Hirono, 1981, Carcinogenicity examination of quercetin and rutin in ACI rats, Cancer Lett., 13, 15, 10.1016/0304-3835(81)90081-1

Hirose, 1983, Effect of quercetin on two-stage carcinogenesis of the rat urinary bladder, Cancer Lett., 21, 23, 10.1016/0304-3835(83)90078-2

Ito, 1989, Lack of carcinogenicity of quercetin in F334/DuCrj rats, Jpn. J. Cancer Res., 80, 317, 10.1111/j.1349-7006.1989.tb02313.x

Ito, 1992, Is quercetin carcinogenic?, Jpn. J. Cancer Res., 83, 312, 10.1111/j.1349-7006.1992.tb00106.x

IUPAC-IUB Joint Commission on Biochemical Nomenclature, 1982. Nomenclature of tocopherols and related compounds. Recommendations 1981. Eur. J. Biochem. 123, 473.

Iverson, 1996, Bioactivation of estrone and its catechol metabolites to quinoid–glutathione conjugates in rat liver microsomes, Chem. Res. Toxicol., 9, 492, 10.1021/tx950178c

Kameoka, 1999, Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids, Cancer Lett., 146, 161, 10.1016/S0304-3835(99)00253-0

Kline, 1989, Modulation of immune suppression and enhanced tumorigenesis in retrovirus tumor challenged chickens treated with vitamin E, In Vivo, 3, 161

Kushi, 1996, Dietary antioxidant vitamins and death from coronary heart disease in postmenopausal women, New Engl. J. Med., 334, 1156, 10.1056/NEJM199605023341803

Laughton, 1989, Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin, Biochem. Pharmacol., 38, 2859, 10.1016/0006-2952(89)90442-5

Lee, 2001, Vitamin C-induced decomposition of lipid hydroperoxides to endogenous genotoxins, Science, 292, 208, 10.1126/science.1059501

Legha, 1982, Clinical and pharmacologic investigation of the effects of α-tocopherol on adriamycin cardiotoxicity, Ann. NY Acad. Sci., 393, 411, 10.1111/j.1749-6632.1982.tb31279.x

Lippman, 1998, Cancer chemoprevention: progress and promise, J. Natl. Cancer Inst., 90, 1514, 10.1093/jnci/90.20.1514

Lotan, 1999, Lung cancer promotion by β-carotene and tobacco smoke: relationship to suppression of retinoic acid receptor-β and increased activator protein-1, J. Natl. Cancer Inst., 91, 7, 10.1093/jnci/91.1.7

MacGregor, 1978, Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium, Mut. Res., 54, 297, 10.1016/0165-1161(78)90020-1

Matter, 1992, The inhibition of phosphatidylinositol 3-kinase by quercetin and analogs, Biochem. Biophys. Res. Commun., 186, 624, 10.1016/0006-291X(92)90792-J

Mayne, 1996, Beta-carotene, carotenoids, and disease prevention in humans, FASEB J., 10, 690, 10.1096/fasebj.10.7.8635686

Mayne, 1996, β-Carotene and lung cancer promotion in heavy smokers—a plausible relationship?, J. Natl. Cancer Inst., 88, 1513, 10.1093/jnci/88.21.1516-a

Metodiewa, 1999, Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product, Free Rad. Biol. Med., 26, 107, 10.1016/S0891-5849(98)00167-1

Middleton, 1994, The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer, 619

Miller, 1996, Antioxidant activities of carotenes and xanthophylls, FEBS Lett., 384, 240, 10.1016/0014-5793(96)00323-7

Mitchel, 1993, Vitamin E is a complete tumor promotor in mouse skin, Carcinogenesis, 14, 659, 10.1093/carcin/14.4.659

Morino, 1982, Carcinogenicity test of quercetin and rutin in golden hamsters by oral administration, Carcinogenesis, 3, 93, 10.1093/carcin/3.1.93

Mortensen, 1997, Importance of carotenoid structure in radical-scavenging reactions, J. Agric. Food Chem., 45, 2970, 10.1021/jf970010s

Murthy, 1992, Polycyclic hydrocarbon (PAH) ortho-quinone conjugate chemistry: kinetics of thiol addition to PAH ortho-quinones and structures of thioether adducts of naphtalene-1,2-dione, Chem. Biol. Interact., 84, 169, 10.1016/0009-2797(92)90077-X

Myers, 1976, Adriamycin: amelioration of toxicity by α-tocopherol, Cancer Treat. Rep., 60, 961

Myers, 1977, Adriamycin: the role of lipid peroxidation in cardiac toxicity and tumor response, Science, 197, 165, 10.1126/science.877547

Nitta, 1991, Induction of transplantable tumors by repeated subcutaneous injections of natural and synthetic vitamin E in mice and rats, Jpn. J. Cancer Res., 82, 511, 10.1111/j.1349-7006.1991.tb01880.x

Nitta, 1991, Effects of administration of natural vitamin E on spontaneous hepatocarcinogenesis and N-dinitrosodiethylamine initiated tumors in mice, J. Toxicol. Pathol., 4, 55, 10.1293/tox.4.55

NTP, 1991. NTP technical report (TR-409) Toxicology and carcinogenesis studies of quercetin (Cas No. 117-39-5) in F344 rats (Feed studies). NI publication No 91-3140, U.S. Department of Health and Human Services, Public Health Service, National Toxicology program, Research Triangle Park, NC.

Ocké, 1997, Repeated measurements of vegetables, fruits, β-carotene and vitamins C and E in relation to lung cancer, Am. J. Epidemiol., 145, 358, 10.1093/oxfordjournals.aje.a009113

Omaye, 1997, Carotene: friend or foe?, Fundam. Appl. Toxicol., 40, 163, 10.1006/faat.1997.2387

Omenn, 1996, Effects of a combination of beta carotene and vitamin A on lung cancer and cardiovascular disease, N. Engl. J. Med., 334, 1150, 10.1056/NEJM199605023341802

Omenn, 1996, Micronutrients (vitamins and minerals) as cancer-preventive agents, IARC Sci. Publ., 139, 33

Palozza, 1992, β-Carotene and α-tocopherol are synergistic antioxidants, Arch. Biochem. Biophys., 297, 184, 10.1016/0003-9861(92)90658-J

Palozza, 1995, Prooxidant activity of β-carotene under 100% oxygen pressure in rat liver microsomes, Free Rad. Biol. Med., 19, 887, 10.1016/0891-5849(95)00094-E

Pamukcu, 1980, Quercetin, a rat intestinal and bladder carcinogen present in bracken fern (Pteridium aquilinum), Cancer Res., 40, 3468

Penning, 1999, Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: generation of reactive and redox-active o-quinones, Chem. Res. Toxicol., 12, 1, 10.1021/tx980143n

Peto, 1981, Can dietary beta-carotene materially reduce human cancer rates?, Nature, 290, 201, 10.1038/290201a0

Pietta, 2000, Flavonoids as antioxidants, J. Nat. Prod., 63, 1035, 10.1021/np9904509

Podmore, 1998, Vitamin C exhibits pro-oxidant properties, Nature, 392, 559, 10.1038/33308

Rice-Evans, 1996, Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Rad. Biol. Med., 20, 933, 10.1016/0891-5849(95)02227-9

Rom, 1987, Characterization of the lower respiratory tract inflammation of non-smoking individuals with interstitial lung disease associated with chronic inhalation of inorganic dusts, Am. Rev. Respir. Dis., 136, 1429, 10.1164/ajrccm/136.6.1429

Sakagami, 1997, Modulating factors of radical intensity and cytotoxic action of ascorbate, Anticancer Res., 17, 3513

Sakagami, 2000, Apoptosis-inducing activity of vitamin C and vitamin K, Cell. Mol. Biol., 46, 129

Samuni, 1983, On the cytotoxicity of vitamin C and metal ions, Eur. J. Biochem., 137, 119, 10.1111/j.1432-1033.1983.tb07804.x

Scambia, 1991, Quercetin inhibits the growth of a multidrug resistant estrogen-receptor-negative MCF-7 human breast-cancer cell line expressing type II estrogen binding sites, Cancer Chemother. Pharmacol., 28, 255, 10.1007/BF00685531

Sen, 1996, Antioxidant and redox regulation of gene transcription, FASEB J., 10, 709, 10.1096/fasebj.10.7.8635688

Shinozawa, 1988, Effect of high dose α-tocopherol and α-tocopherol acetate pretreatment on adriamycin (doxorubicin) induced toxicity and tissue distribution, Physiol. Chem. Phys. Med. NMR, 20, 329

Soffers, 1999, Quantitative structure antioxidant activity relationships for carotenoids, Free Rad. Res., 30, 233, 10.1080/10715769900300251

Sonneveld, 1978, Effect of α-tocopherol on the cardiotoxicity of adriamycin in the rat, Cancer Treat. Rep., 62, 1033

Stähelin, 1991, Plasma antioxidant vitamins and subsequent cancer mortality in the 12-year follow-up of the prospective Basel study, Am. J. Epidemiol., 133, 766, 10.1093/oxfordjournals.aje.a115955

Stahl, 1998, Carotenoid mixtures protect multilamellar liposomes against oxidative damage: synergistic effects of lycopene and lutein, FEBS Lett., 427, 305, 10.1016/S0014-5793(98)00434-7

Stampfer, 1993, Vitamin E consumption and the risk of coronary disease in women, N. Engl. J. Med., 328, 1444, 10.1056/NEJM199305203282003

Stephens, 1996, Randomised controlled trial of vitamin E in patients with coronary disease: Cambridge heart antioxidant study (CHAOS), Lancet, 347, 781, 10.1016/S0140-6736(96)90866-1

Stocker, 1999, The ambivalence of vitamin E in atherogenesis, TIBS, 24, 219

Stoewsand, 1984, Quercetin: a mutagen, not a carcinogen in Fisher rats, J. Toxicol. Environ. Health, 14, 105, 10.1080/15287398409530565

Sudhar, 1990, Redox potential of some sulfur containing radicals, J. Phys. Chem., 94, 5915

Temple, 1987, Cabbage and vitamin E: their effect on colon tumor formation in mice, Cancer Lett., 35, 71, 10.1016/0304-3835(87)90058-9

1994, The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers, N. Engl. J. Med., 330, 1029, 10.1056/NEJM199404143301501

Toth, 1983, Enhancing effect of vitamin E on murine intestinal tumorigenesis by 1,2-dimethylhydrazine dihydrochloride, J. Natl. Cancer Inst., 70, 1107

Van Haaften, 2001, Inhibition of human glutatione-S-transferase P1-1 by tocopherols and alpha-tocopherol derivatives, Biochim. Biophys. Acta, 1548, 23, 10.1016/S0167-4838(01)00211-4

Virtamo, 1999, Vitamins and lung cancer, Proc. Nutr. Soc., 58, 329, 10.1017/S0029665199000440

Wang, 1980, Effect of vitamin E against adriamycin-induced toxicity in rabbits, Cancer Res., 40, 1022

Wang, 1999, Retinoid signaling and activator protein-1 expression in ferrets given β-carotene supplements and exposed to tobacco smoke, J. Natl. Cancer Inst., 91, 60, 10.1093/jnci/91.1.60

Weitzman, 1980, Prospective study of tocopherol prophylaxis for anthracycline cardiac toxicity, Curr. Ther. Res., 28, 682

Williamson, 2000, Human metabolic pathways of dietary flavonoids and cinnamates, Biochem. Soc. Transact., 28, 16, 10.1042/bst0280016

Woodall, 1997, Oxidation of carotenoids by free radicals: relationship between structure and reactivity, Biochim. Biophys. Acta, 1336, 33, 10.1016/S0304-4165(97)00006-8

Yamashita, 1998, α-Tocopherol induces oxidative damage to DNA in the presence of copper(II) ions, Chem. Res. Toxicol., 11, 855, 10.1021/tx970129v

Yong, 1997, Intake of vitamins E, C and A and risk of lung cancer. The NHANES I epidemiologic followup study, Am. J. Epidemiol., 146, 231, 10.1093/oxfordjournals.aje.a009258

Ziegler, 1991, Vegetables, fruits and carotenoids and the risk of cancer, Am. J. Clin. Nutr., 53, 251S, 10.1093/ajcn/53.1.251S

Zhu, 1994, Catechol-O-methyltransferase-catalyzed rapid O-methylation of mutagenic flavonoids. Metabolic inactivation as a possible reason for their lack of carcinogenicity in vivo, J. Biol. Chem., 269, 292, 10.1016/S0021-9258(17)42348-9

Zhu, 1996, Inhibition of catechol O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by quercetin. Possible role in estrogen-induced tumorigenesis, J. Biol. Chem., 271, 1357, 10.1074/jbc.271.3.1357