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Vol. 31, Issue 4, 452-461, April 2003

Glucuronides of Tea Catechins: Enzymology of Biosynthesis and Biological Activities

Hong Lu, Xiaofeng Meng, Chuan Li, Shengmin Sang, Christopher Patten, Shuqun Sheng, Jungil Hong, Naisheng Bai, Bozena Winnik, Chi-Tang Ho, and Chung S. Yang

Department of Chemical Biology, Ernest Mario School of Pharmacy (H.L., X.M., C.L., J.H., C.S.Y.); Department of Food Science and Center for Advanced Food Technology (S.Sa., N.B., C-T.H); Department of Chemistry, Rutgers, the State University of New Jersey, Piscataway, New Jersey (S.Sh.); Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China (C.L.); BD Biosciences, Woburn, Massachusetts (C.P.); and Environmental and Occupational Health Sciences Institute, Piscataway, New Jersey (B.W., C.S.Y.)

(-)-Epigallocatechin gallate (EGCG) and (-)-epigallocatechin (EGC) are major green tea catechins with antioxidant and anticancer activities. In this study, we characterized the glucuronidation of EGCG and EGC in human, mouse, and rat microsomes and by nine different human UGT 1A and 2B isozymes expressed in insect cells. Six EGCG and EGC glucuronides were biosynthesized, and their structures were identified for the first time. (-)-EGCG-4"-O-glucuronide was the major EGCG glucuronide formed in all incubations. The catalytic efficiency (Vmax/Km) for (-)-EGCG-4"-O-glucuronide formation followed the order: mouse intestine > mouse liver > human liver > rat liver rat small intestine. The UGT-catalyzed glucuronidation of EGC was much lower than that of EGCG. The Vmax/Km for (-)-EGC-3'-O-glucuronide followed the following order: mouse liver > human liver > rat liver > rat and mouse small intestine. Human UGT1A1, 1A8, and 1A9 had high activities with EGCG. UGT1A8, an intestine-specific UGT, had the highest Vmax/Km for EGCG but low activity with EGC. Mice appeared to be more similar to humans than rats to humans in the glucuronidation of EGCG and EGC. Some of these catechin glucuronides retained the activities of their parent compounds in radical scavenging and in inhibiting the release of arachidonic acid from HT-29 human colon cancer cells. These results provide foundations for understanding the biotransformation and biological activities of tea catechins.

Copyright © 2003 by The American Society for Pharmacology and Experimental Therapeutics


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Copyright © 2003 by the American Society for Pharmacology and Experimental Therapeutics.