Antioxidative and Cytoprotective Effects of Isoflavones Isolated from Pueraria thunbergiana Flowers

갈화에서 분리한 이소플라본의 항산화 및 세포보호효과

  • 이경태 (경희대학교 약학대학 약학과) ;
  • 손일철 (경희대학교 약학대학 약학과) ;
  • 공은아 (경희대학교 약학대학 약학과) ;
  • 김동현 (경희대학교 약학대학 약학과) ;
  • 최승기 (분당차병원) ;
  • 최종원 (경성대학교 약학대학) ;
  • 박희준 (상지대학교 응용식물과학부)
  • Published : 1999.12.01

Abstract

Antioxidative and cytoprotective effects of tectorigenin and glycitein isolated from the pueraria thunbergiana and its derivative, genistein, were determined. Among these three compounds, tectorigenin and glycitein bearing 6-methoxyl groups in both isoflavones showed significant free radical scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and xanthine/xanthine oxidase (XOD) generating superoxide anion radical. Tectorigenin only showed a slight inhibitory effect on XOD. We further studied the inhibitory effects of these isoflavones on the lipid peroxidation in rat liver microsomes induced by enzymatic and non-enzymatic methods. Each of them exhibited inhibitory effect on both ascorbic $acid/Fe^{2+}-{\;}and{\;}ADP/NADPH/Fe^{+3}-induced$ lipid peroxidation. Moreover, tectorigenin exhibited the highest protection of hydrogen peroxide damage on HepG2 and Vero cells among the three isoflavones, in the cytoprotective assay. It was suggested that the pattern of antioxidative and cytoprotective effect of isoflavones could be crucially by the aromatic substitution of oxygen-containing groups.

Keywords

References

  1. Nutr. Cancer v.21 Soy intake and cancer risk: a review of the in vitro and in vivo data Messina, M. J.;Persky, V.;Setchell, K. D.;Barnes, S.
  2. J. Am. Diet. Assoc. v.91 Increasing use of soyfoods and their potential role in cancer prevention Messina, M.;Messina, V.
  3. Br. J. Nutr. v.74 Biological effects of isoflavones in young women: importance of the chemical composition of soybean products Cassidy, A.;Bingham, S.;Setchell, K.
  4. Cell Growth Differ. v.7 Genistein inhibits both estrogen and growth factor stimulated proliferation of human breast cancer cells Peterson, G.;Barnes, S.
  5. Transplant Proc. v.28 Genistein suppresses cellular injury following hepatic ischemia/reperfusion Yamamoto, S.;Shimizu, K.;Oonishi, I.;Hasebe, K.;Takamura, H.;Inoue, T.;Muraoka, K.;Tani, T.;Hashimoto, T.;Yagi, M.
  6. J. Nutr. v.126 Soybean isolavones improve cardiovascular risk factors without affecting the reproductive system of peripubertal rhesus monkeys Anthony, M. S.;Clarkson, T. B.;Hughes, C. L. Jr.;Morgan, T. M.;Burke, G. L.
  7. Biochem. Pharmacol. v.39 Induction of mammalian topoisomerase II dependent DNA cleavage by nonintercalative flavonoids genistein and orobol Yamashita, Y.;Kawada, S.;Nakano, H.
  8. Nutr. Cancer v.25 Effect of dietary genistein on antioxidant enzyme activities in SENCAR mice Cai, Q.;Wei, H.
  9. Nutr. Cancer v.20 Inhibition of tumor promoter-induced hydrogen peroxide formation in vitro and in vivo by genistein Wei, H.;Wei, L.;Frenkel, K.;Bowen, R.;Barnes, S.
  10. Lancet v.16 Susceptibility to low-density lipoprotein oxidation and coronary atherosclerosis in man Regnstrom, J.;Nilsson, J.;Tornvall, P.;Landou, C.;Hamsten, A.
  11. Am. J. Clin. Nutr. v.53 Inverse correlation between plasma vitamin E and mortality from ischemic heart disease in crosscultural epidemiology Gey, K. F.;Puska, P.;Jordan, P.;Moser, U. K.
  12. Yakugaku Zasshi v.95 Studies on the constituents of flowers V. On the components of flowers of Pueraria thunbergiana Benth. (2). Isolation of a new isoflavone glycoside Kurihara, T.;Kikuchi, M.
  13. Yakugaku Zasshi v.93 Studies on the constituents of FLowes. I. On the components of flower of Pueraria thunbergiana Benth Kurihara, T.;Kikuchi, M.
  14. Yakugaku Zasshi v.96 Studies on the constituents flowers VI. On the components of flowers of Pueraria thunbergiana Benth Kurihara, T.;Kikuchi, M.
  15. The 29th annual meeting of the Korean Society of Pharmacognosy Inhibition of inflammatory mediators by sesquiterpenes from Ligularia fischerii Hwang, B. Y.;Gu, T. H.;Lee, J. H.;Roh, J. S.;Lee, K. S.;Lee, J. J.
  16. Phytochemistry v.51 Isoflavone glycoside from the flower of Pueraria thunbergiana Park, H. J.(ed.);Moon, J. O.;Lee, K. T.;Jung, W. T.;Oh, S. R.;Lee, H. K.
  17. Chem. Pharm. Bull. v.36 Studies on the constituents of Pueraria lobata. IV. Chemical constituents in the flowers and leaves Kinjo, J.;Takeshita, T.;Abe, Y.;Terada, N.;Yamashita, H.;Yamasaki, M.;Takeuch, K.;Murakami, K.;Tomimatsu, T.;Nohara, T.
  18. Planta Med. v.62 Prevention of hydrogen peroxide damage by soybean saponins to mouse fibroblasts Yoshikoshi, M.;Yoshiki, Y.;Okubo, Y.;Seto, K.;Sasaki, Y.
  19. Biol. Pharm. Bull. v.20 Preventive effects of saponins from Puerariae Radix(the root of Pueraria lobata Ohwi) on in Vitro immunological injury of rat primary hepatocyte cultures Arao, T.;Udayama, M.;Kinjo, J.;Nohara, T.;Funakoshi, T.;Kojima, S.
  20. Planta Med. v.50 Mechanism of antihepatotoxic activity of glycyrrhizin Kiso, Y.;Tohkin, M.;Hikio, H.;Hattori, M.;Sakamoto, T.;Namba, Y.
  21. Anal. Biochem. v.72 A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of portein-day binding Bradford, M. M.
  22. Arch. Pharm. Res. v.21 Induction of differentiation of the human histocytic lymphoma cell line U-937 by hypericin Kim,J.I.;Park,J.H(ed.);Choi,S.K.;Lee, K. T.
  23. Biol. Pharm. Bull. v.19 Antioxidative effects of phenylethanoids from Cistanche deserticola Xiong, Q.;Kadota, S.;Tani, T.;Namba, T.
  24. Arch. Biochem. Biophys. v.356 Antioxidant activities of isoflavones and their biological metabolites in a liposomal system Arora, A.;Nair, M. G.;Strasburg, G. M.
  25. Proc. Soc. Exp. Biol. Med. v.208 Antioxidant and antipromotional effects of the soybean isoflavone genistein Wei, H.;Bowen, R.;Cai, Q.;Barnes, S.;Wang, Y.
  26. Gann. v.75 Generation of hydrogen peroxide and superoxide anion radical from cigarette smoke Nakayama, T.;Kodama, M.;Nagata, C.
  27. Arterioscler. Thromb. Vasc. Biol. v.17 Genistein, the dietary-derived angiogenesis inhibitor, prevents LDL oxidation and protects endothelia cells from damage by atherogenic LDL Kapiotis, S.;Hermann, M.;Held, I.;Seelos, C.;Ehringer, H.;Gmeiner, B. M.
  28. Biochem. Soc. Trans. v.25 Inhibition of protein tyrosine phosphorylation in endothelial cells: relationship to antiproliferative action of genistein Koroma, B. M.;Juan, E. Jr.
  29. J. Biochem. v.118 A 96-kDa glycyrrhizin-binding for casein kinase II, and is highly related to lipoxigenase 3 Ohtsuki, K.;Nakamura, S.;Shimoyama, Y.;Shibata, D.;Munakata, H.;Yoshiki, Y.;Okubo, K.
  30. Harper's Biochemistry(24th ed.) Murray, R. K.;Granner, D. K.;Mayes, P. A.;Rodwell, V. W.