Antioxidant effects of isoflavonoids and lignans, and protection against DNA oxidation

References

• Wiseman H., Halliwell B. Damage to DNA by reactive oxygen and nitrogen species: role in inflammatory disease and progression to cancer. Biochemical Journal 1996; 313: 17–29
   PubMed Web of Science ®Google Scholar
• Halliwell B., Gutteridge J.M.C. Oxygen toxicity, oxygen radicals, transition metals and disease. Biochemical Journal 1984; 219: 1–14
   PubMed Web of Science ®Google Scholar
• Aruoma O.I., Halliwell B., Gajewski E., Dizdaroglu M. Damage to the bases in DNA induced by hydrogen peroxide and ferric ion chelates. Journal of Biological Chemistry 1989; 264: 20509–20512
   PubMed Web of Science ®Google Scholar
• Adlercreutz H., Honjo H., Higashi A., Fotsis T., Hämäläinen E., Hasegawa T., Okada H. Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese diet. American Journal of Clinical Nutrition 1991; 54: 1093–1100
   PubMed Web of Science ®Google Scholar
• Messina M.J., Persky V., Setchell K.D.R., Barnes S. Soy intake and cancer risk: a review of the in vitro and in vivo data. Nutrition and Cancer 1994; 21: 113–131
   PubMed Web of Science ®Google Scholar
• Lee H.P., Gourley L., Duffy S.W., Estève J., Lee J., Day N.E. Dietary effects on breast-cancer risk in Singapore. The Lancet 1991; 337: 1197–1200
   PubMed Web of Science ®Google Scholar
• Barnes S., Grubbs G., Setchell K.D.R., Carlson J. Soybeans inhibit mammary tumours in models of breast cancer. Mutagens and Carcinogens in the Diet, M. Pariza. Wiley-Liss, New York 1990; 239–253
   Google Scholar
• Adlercreutz T. Phytoestrogens: epidemiology and a possible role in cancer protection. Environmental Health Perspectives 1995; 103: 103–112
   PubMed Web of Science ®Google Scholar
• Herman C., Adlecreutz T., Goldin B.R., Gorbach S.L., Höckerstedt K.A.V., Watanabe S., Hämäläinen E.K., Markkanen M.H., Mäkela T.H., Wähälä K.T., Hase T.A., Fotsis T. Soybean phytoestrogen intake and cancer risk. American Institute of Nutrition 1995; 125: 757S–770S
   PubMed Web of Science ®Google Scholar
• Wiseman H. Role of dietary phyto-oestrogens in the protection against cancer and heart disease. Biochemical Society Transactions 1996; 24: 795–800
   PubMed Web of Science ®Google Scholar
• Clarkson T.B., Anthony M.S., Hughes C.L., Jr. Estrogenic soybean isoflavones and chronic disease. Risks and benefits. Trends in Endocrinology and Metabolism 1995; 6: 11–16
   PubMed Web of Science ®Google Scholar
• Wei H., Bowen R., Cai Q., Barnes S., Wang Y. Antioxidant and antipromotional effects of the soybean isoflavone genistein. Proceedings of the Society of Experimental Biology and Medicine 1995; 208: 124–130
   PubMed Web of Science ®Google Scholar
• Cai Q., Wei H. Effect of dietary genistein on antioxidant enzyme activities in SENCAR mice. Nutrition and Cancer 1996; 25: 1–7
   PubMed Web of Science ®Google Scholar
• Goodman Y., Steiner M.R., Steiner S.M., Mattson M.P. Nordihydroguaiaretic acid protects hippocampal neurons against amyloid β-peptide toxicity, and attenuates free radical and calcium accumulation. Brain Research 1994; 654: 171–176
   PubMed Web of Science ®Google Scholar
• Puppo A. Effect of flavonoids on hydroxyl radical formation by Fenton-type reactions; influence of the iron chelator. Phytochemistry 1992; 31: 85–88
   Web of Science ®Google Scholar
• Afanas'ev I.B., Dorozhko A.I., Brodskii A.V., Kostyuk V.A., Potapovitch A.I. Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation. Biochemical Pharmacology 1989; 38: 1763–1769
   PubMed Web of Science ®Google Scholar
• Laughton M.J., Halliwell B., Evans P.J., Hoult J.R.S. Antioxidant and prooxidant actions of the plant phenolics quercetin, gossypol and myricetin. Biochemical Pharmacology 1989; 38: 2859–2865
   PubMed Web of Science ®Google Scholar
• Bors W., Heller W., Michel C., Saran M. Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods in Enzymology 1990; 186: 343–355
   PubMed Web of Science ®Google Scholar
• Bors W., Michel C., Saran M. Flavonoid antioxidants: rate constants for reactions with oxygen radicals. Methods in Enzymology 1994; 234: 420–429
   PubMed Web of Science ®Google Scholar
• Husain S.R., Cillard J., Cillard P. Hydroxyl radical scavenging activity of flavonoids. Phytochemistry 1987; 26: 2489–2491
   Web of Science ®Google Scholar
• Sahu S.C. Dual role of flavonoids in mutagenesis and carcinogenesis. Environmental Carcinogenesis Ecotoxicology Reviews 1994; 12: 1–21
   Web of Science ®Google Scholar
• Torel J., Cillard J., Cillard P. Antioxidant activity of flavonoids and reactivity with peroxy radical. Phytochemistry 1986; 25: 383–386
   Web of Science ®Google Scholar
• Sanz M.J., Ferrandiz M.L., Cejudo M., Terencio M.C., Gil B., Bustos G., Ubeda A., Gunasegaran R., Alcaraz M.J. Influence of a series of natural flavonoids on free radical generating systems and oxidative stress. Xenobiotica 1994; 24: 689–699
   PubMed Web of Science ®Google Scholar
• Rios J.R., Manñez S., Paya M., Alcaraz M.J. Antioxidant activity of flavonoids from Sideritis Javalambrensis. Phytochemistry 1992; 31: 1947–1950
   PubMed Web of Science ®Google Scholar
• Fauré M., Lissi E., Torres R., Videla L.A. Antioxidant activities of lignans and flavonoids. Phytochemistry 1990; 29: 3773–3775
   Web of Science ®Google Scholar
• Morel I., Lescoat G., Cogrel P., Sergent O., Pasdeloup N., Brissot P., Cillard P., Cillard J. Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded hepatocyte cultures. Biochemical Pharmacology 1993; 45: 13–19
   PubMed Web of Science ®Google Scholar
• Payá M., Halliwell B., Hoult J.R.S. Interactions of a series of coumarins with reactive oxygen species; scavenging of superoxide, hypochlorous acid and hydroxyl radicals. Biochemical Pharmacology 1992; 44: 205–214
   PubMed Web of Science ®Google Scholar
• Kelly G.E., Joannou G.E., Reeder A.Y., Nelson C., Waring M.A. The variable metabolic response to dietary isoflavones in humans. Proceedings of the Society for Experimental Biology and Medicine 1995; 208: 40–43
   PubMed Web of Science ®Google Scholar
• Wei H., Wei L., Frenkel K., Bowen R., Barnes S. Inhibition of tumor promoter-induced hydrogen peroxide formation in vitro and in vivo by genistein. Nutrition and Cancer 1993; 20: 1–12
   PubMed Web of Science ®Google Scholar
• Wei H., Cai Q., Rahn R.O. Inhibition of UV light- and Fenton reaction-induced oxidative DNA damage by the soybean isoflavone genistein. Carcinogenesis 1996; 17: 73–77
   PubMed Web of Science ®Google Scholar
• Ruiz-Larrea M.B., Mohan A.R., Paganga G., Miller N.J., Bolwell G.P., Rice-Evans C.A. Antioxidant activity of phytoestrogenic isoflavones. Free Radical Research 1997; 26: 63–70
   PubMed Web of Science ®Google Scholar
• Javitt N.B. Hep G2 cells as a resource for metabolic studies: lipoprotein, cholesterol, and bile acids. FASEB Journal 1990; 4: 161–168
   PubMed Web of Science ®Google Scholar
• Kasai H., Crain P.F., Kuchino Y., Nishimura S., Ootsuyama A., Tanooka H. Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis 1986; 7: 1849–1851
   PubMed Web of Science ®Google Scholar
• Floyd R.A. The role of 8-oxodeoxyguanosine in carcinogenesis. Carcinogenesis 1990; 11: 1447–1450
   PubMed Web of Science ®Google Scholar
• Allan I.M., Vaughan A.T.M., Milner A.E., Lunec J., Bacon P.A. Structural damage to lymphocyte nuclei by H2O2 or gamma irradiation is dependent on the mechanism of OH· radical production. British Journal of Cancer 1988; 58: 34–37
   PubMed Web of Science ®Google Scholar
• Udenfriend S., Clark C.T., Axelrod J., Brodie B.B. Ascorbic acid in aromatic hydroxylation. I. A model system for aromatic hydroxylation. Journal of Biological Chemistry 1954; 208: 731–739
   PubMed Web of Science ®Google Scholar
• Winyard P.G., Perrett D., Blake D.R., Harris G., Chipman J.K. Measurement of DNA oxidation products. Analytical Proceedings 1990; 27: 224–227
   Google Scholar
• Doostdar H., Duthie S.J., Burke M.D., Melvin W.T., Grant M.H. The influence of culture medium composition on drug metabolising enzyme activities of the human liver derived HepG2 cell line. FEBS Letters 1988; 241: 15–18
   PubMed Web of Science ®Google Scholar
• Rosenkranz A.R., Schmaldienst S., Stuhlmeier K.M., Chen W., Knapp W., Zlabinger G.J. A microplate assay for the detection of oxidative products using 2′,7′-dichlorofluorescin-diacetate. Journal of Immunology Methods 1992; 156: 39–45
   PubMed Web of Science ®Google Scholar
• Floyd R.A., Watson J.J., Wong P.K., Altmiller D.H., Richard R.C. Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanisms of formation. Free Radical Research Communications 1986; 1: 163–172
   PubMedGoogle Scholar
• Royall J.A., Ischiropoulos H. Evaluation of 2′,7′-dichlorofluorescin and dihydrorhodamine 123 as fluorescent probes for infracellular H2O2 in cultured endothelial cells. Archives of Biochemistry and Biophysics 1993; 302: 348–355
   PubMed Web of Science ®Google Scholar
• Masaki N., Kyle M.E., Farber J.L. Tert-butyl hydroperoxide kills cultured hepatocytes by peroxidizing membrane lipids. Archives of Biochemistry and Biophysics 1989; 269: 390–399
   PubMed Web of Science ®Google Scholar
• Bartoli G.M., Piccioni E., Agostara G., Calviello G., Palozza P. Different mechanisms of tert-butyl hydroperoxide-induced lethal injury in normal and tumor thymocytes. Archives of Biochemistry and Biophysics 1994; 312: 81–87
   PubMed Web of Science ®Google Scholar
• Cadenas F., Sies H. Low level chemiluminescence of liver microsomal fractions initiated by tert-butyl hydroperoxide. European Journal of Biochemistry 1982; 124: 349–356
   PubMedGoogle Scholar
• Boveris A., Fraga C.G., Varsavsky A.I., Koch O.R. Increased chemiluminescence and superoxide production in the liver of chronically ethanol-treated rats. Archives of Biochemistry and Biophysics 1983; 227: 534–541
   PubMed Web of Science ®Google Scholar
• LeBel C.P., Ischiropoulos H., Bondy S.C. Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chemical Research Toxicology 1992; 5: 227–231
   PubMed Web of Science ®Google Scholar
• Cathcart R., Schwiers E., Ames B.N. Detection of picomole levels of hydroperoxides using a fluorescent dichlorofluorescin assay. Analytical Biochemistry 1983; 134: 111–116
   PubMed Web of Science ®Google Scholar
• Kuo S.-M. Antiproliferative potency of structurally distinct dietary flavonoids on human colon cancer cells. Cancer Letters 1996; 110: 41–48
   PubMed Web of Science ®Google Scholar
• Martin K.R., Failla M.L., Smith J.C., Jr. β-Carotene and lutein protect HepG2 human liver cells against oxidant-induced damage. Journal of Nutrition 1996; 126: 2098–2106
   PubMed Web of Science ®Google Scholar
• Rice-Evans C.A., Miller N.J., Paganga G. Structure-antioxidant activity relationships of flavonoids and phlenolic acids. Free Radicals in Biology and Medicine 1996; 20: 933–956
   PubMed Web of Science ®Google Scholar
• vanAcker S.A.B.E., vandenBerg D.J., Trump M.N.J.L., Griffioen D.H., VanBennekom W.P., VanderVijgh W.J.F., Bast A. Structural aspects of antioxidant activity of flavonoids. Free Radicals in Biology and Medicine 1996; 20: 331–342
   PubMed Web of Science ®Google Scholar