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J.Health Sci., 53(5), 591-595, 2007

Copper(II) Ions Convert Catechins from Antioxidants to Prooxidants in Protein Carbonyl Formation

Kazuo Nakagawa*, a Maiko Kaku,a Tomomi Abukawa,a Kanako Aratani,a Mariko Yamaguchi,a and Shinichi Uesatob, c

aDepartment of Food and Nutrition, Faculty of Home Economics, Kyoto Women’s University, 35 Kitahiyoshi-cho, Imakumano, Higashiyama-ku, Kyoto 605-8501, Japan, bDepartment of Biotechnology, Faculty of Engineering, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japan, and cHigh Technology Research Center, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japan

Catechins are naturally occurring polyphenols, which are supposed to have antioxidative effects on foods and living cells. We examined the antioxidative effects of (+)-catechin and 3-O-acyl derivatives of (+)-catechin in combination with copper(II) [Cu(II)] ions on the formation of carbonyl groups in bovine serum albumin (BSA) at pH 7.4 by incubating in vitro for 90 min at 37°C. In the presence of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH), a free radical generator, the formation of carbonyl groups in BSA, which increased time-dependently, was significantly (p<0.05) attenuated by the addition of (+)-catechin and 3-O-acyl-(+)-catechins. However, Cu(II) ions, but not Zn(II) ions, blocked the antioxidative effects of (+)-catechin and 3-O-octanoyl-(+)-catechin on the oxidative modification of BSA induced by AAPH. On the other hand, Cu(II) ions had no influence on the scavenging activity of (+)-catechin for 2,2'-azinobis(3-ethylbenzothiazoline-6-sulphonate) cation radicals. Furthermore, in the absence of AAPH, coexistence of Cu(II) ions with (+)-catechin greatly accelerated the formation of carbonyl groups in BSA, being dependent on the concentrations of Cu(II) ions and (+)-catechin. These results suggest that Cu(II) ions could convert (+)-catechin from an antioxidant to a prooxidant in protein oxidation.