The antioxidant activity of daidzein metabolites, O-desmethylangolensin and equol, in HepG2 cells

Molecular Medicine Reports

Volumn 9, Issue 1, 2014, Pages 328-332

  Choi, Eun Jeong ^a   Kim, Gun Hee ^a  

^a Duksung Women's University   (South Korea)

Author keywords

Antioxidant; Cytotoxicity; Daidzein; Daidzin; Equol; In vitro; O desmethylangolensin

Indexed keywords

ANTIOXIDANTS; CATALASE; CELL PROLIFERATION; EQUOL; HEP G2 CELLS; HUMANS; ISOFLAVONES; L-LACTATE DEHYDROGENASE; SUPEROXIDE DISMUTASE;

EID: 84893844544     PISSN: 17912997     EISSN: 17913004     Source Type: Journal    
DOI: 10.3892/mmr.2013.1752     Document Type: Article

References (39)

1. Bors W, Michel C and Stettmaier K: Antioxidant effects of flavonoids. Biofactors 6: 399-402, 1997.
2. Kris-Etherton PM and Keen CL: Evidence that the antioxidant flavonoids in tea and cocoa are beneficial for cardiovascular health. Curr Opin Lipidol 13: 41-49, 2002.
3. Hirooka Y, Sagara Y, Kishi T and Sunagawa K: Oxidative stress and central cardiovascular regulation. Pathogenesis of hypertension and therapeutic aspects. Circ J 74: 827-835, 2010.
4. Reuter S, Gupta SC, Chaturvedi MM and Aggarwal BB: Oxidative stress, inflammation, and cancer: how are they linked? Free Radic Biol Med 49: 1603-1616, 2010.
5. L'homme R, Brouwers E, Al-Maharik N, Lapcík O, Hampl R, Mikola H, Wähälä K and Adlercreutz H: Time-resolved fluoroimmunoassay of plasma and urine O-desmethylangolensin. J Steroid Biochem Mol Biol 81: 353-361, 2002.
6. Arai Y, Uehara M, Sato Y, Kimira M, Eboshida A, Adlercreutz H and Watanabe S: Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake. J Epidemiol 10: 127-135, 2000.
7. Verheus M, van Gils CH, Keinan-Boker L, Grace PB, Bingham SA and Peeters PH: Plasma phytoestrogens and subsequent breast cancer risk. J Clin Oncol 25: 648-655, 2007.
8. Hwang J, Wang J, Morazzoni P, Hodis HN and Sevanian A: The phytoestrogen equol increases nitric oxide availability by inhibiting superoxide production: an antioxidant mechanism for cell-mediated LDL modification. Free Radic Biol Med 34: 1271-1282, 2003.
9. Turner R, Baron T, Wolffram S, Minihane AM, Cassidy A, Rimbach G and Weinberg PD: Effect of circulating forms of soy isoflavones on the oxidation of low density lipoprotein. Free Radic Res 38: 209-216, 2004.
10. Rüfer CE and Kulling SE: Antioxidant activity of isoflavones and their major metabolites using different in vitro assays. J Agric Food Chem 54: 2926-2931, 2006.
11. Aebi H: Catalase in vitro. Methods Enzymol 105: 121-126, 1984.
12. Marklund S and Marklund G: Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. Eur J Biochem 47: 469-474, 1974.
13. Toda S and Shirataki Y: Comparison of antioxidative and chelating effects of daidzein and daidzin on protein oxidative modification by copper in vitro. Biol Trace Elem Res 79: 83-89, 2001.
14. Messina M: A brief historical overview of the past two decades of soy and isoflavone research. J Nutr 140: 1350S-1354S, 2010.
15. Foti P, Erba D, Riso P, Spadafranca A, Criscuoli F and Testolin G: Comparison between daidzein and genistein antioxidant activity in primary and cancer lymphocytes. Arch Biochem Biophys 433: 421-427, 2005.
16. Setchell KD, Brown NM and Lydeking-Olsen E: The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavones. J Nutr 132: 3577-3584, 2002.
17. Bolca S, Possemiers S, Herregat A, Huybrechts I, Heyerick A, De Vriese S, Verbruggen M, Depypere H, De Keukeleire D, Bracke M, De Henauw S, Verstraete W and Van de Wiele T: Microbial and dietary factors are associated with the equol producer phenotype in healthy postmenopausal women. J Nutr 137: 2242-2246, 2007.
18. Jackman KA, Woodman OL and Sobey CG: Isoflavones, equol and cardiovascular disease: pharmacological and therapeutic insights. Curr Med Chem 14: 2824-2830, 2007.
19. Knasmüller S, Mersch-Sundermann V, Kevekordes S, Darroudi F, Huber WW, Hoelzl C, Bichler J and Majer BJ: Use of human-derived liver cell lines for the detection of environmental and dietary genotoxicants; current state of knowledge. Toxicology 198: 315-328, 2004.
20. Zhang R, Sun J, Ma L, Wu X, Pan G, Hao H, Zhou F, A J, Liu C, Ai H, Shang L, Gao H, Peng Y, Wan P, Wu H and Wang G: Induction of cytochromes P450 1A1 and 1A2 by tanshinones in human HepG2 hepatoma cell line. Toxicol Appl Pharmacol 252: 18-27, 2011.
21. Choi EJ: Chronic equol administration attenuates the antioxidant defense system and causes apoptosis in the mouse brain. Food Chem Toxicol 47: 1779-1784, 2009.
22. Choi EJ: Evaluation of equol function on anti-or prooxidant status in vivo. J Food Sci 74: H65-H71, 2009.
23. Choi EJ: The prooxidant, rather than antioxidant, acts of daidzein in vivo and in vitro: daidzein suppresses glutathione metabolism. Eur J Pharmacol 542: 162-169, 2006.
24. Okayasu H, Ishihara M, Satoh K and Sakagami H: Cytotoxic activity of vitamins K1, K2 and K3 against human oral tumor cell lines. Anticancer Res 21: 2387-2392, 2001.
25. Palozza P, Serini S, Di Nicuolo F, Piccioni E and Calviello G: Prooxidant effects of beta-carotene in cultured cells. Mol Aspects Med 24: 353-362, 2003.
26. Tafazoli S, Wright JS and O'Brien PJ: Prooxidant and antioxidant activity of vitamin E analogues and troglitazone. Chem Res Toxicol 18: 1567-1574, 2005.
27. Watała C, Budziejewska A and Jóźwiak Z: Alloxan-induced alterations in composition and dynamics of red blood cell membranes. I. Effect of alloxan on intact red blood cells and isolated erythrocyte membranes. Biochem Pharmacol 38: 1793-1798, 1989.
28. Jendrossek V: The intrinsic apoptosis pathways as a target in anticancer therapy. Curr Pharm Biotechnol 13: 1426-1438, 2012.
29. Mansilla S, Llovera L and Portugal J: Chemotherapeutic targeting of cell death pathways. Anticancer Agents Med Chem 12: 226-238, 2012.
30. Sosa V, Moliné T, Somoza R, Paciucci R, Kondoh H and LLeonart ME: Oxidative stress and cancer: an overview. Ageing Res Rev 12: 376-390, 2013.
31. Ruiz-Larrea MB, Mohan AR, Paganga G, Miller NJ, Bolwell GP and Rice-Evans CA: Antioxidant activity of phytoestrogenic isoflavones. Free Radic Res 26: 63-70, 1997.
32. Murota K and Terao J: Antioxidative flavonoid quercetin: implication of its intestinal absorption and metabolism. Arch Biochem Biophys 417: 12-17, 2003.
33. Sarkar FH and Li Y: Soy isoflavones and cancer prevention. Cancer Invest 21: 744-757, 2003.
34. Zaitsev M, Steinhoff S and Shah NJ: Error reduction and parameter optimization of the TAPIR method for fast T1 mapping. Magn Reson Med 49: 1121-1132, 2003.
35. Cobb JM, Mattice JD, Senseman SA, Dumas JA, Mersie W, Riley MB, Potter TL, Mueller TC and Watson EB: Stability of pesticides on solid-phase extraction disks after incubation at various temperatures and for various time intervals: interlaboratory study. J AOAC Int 89: 903-912, 2006.
36. Jackman KA, Woodman OL, Chrissobolis S and Sobey CG: Vasorelaxant and antioxidant activity of the isoflavone metabolite equol in carotid and cerebral arteries. Brain Res 1141: 99-107, 2007.
37. Birt DF, Hendrich S and Wang W: Dietary agents in cancer prevention: flavonoids and isoflavonoids. Pharmacol Ther 90: 157-177, 2001.
38. Cotelle N: Role of flavonoids in oxidative stress. Curr Top Med Chem 1: 569-590, 2001.
39. Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M and Telser J: Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 39: 44-84, 2007.