The pro-oxidant chemistry of the natural antioxidants vitamin C, vitamin E, carotenoids and flavonoids
Tóm tắt
Từ khóa
Tài liệu tham khảo
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
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
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
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
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