Chem. Pharm. Bull., 53(7),866-867, July 2005

Communications to the Editor

Biooxidation of (+)-Catechin and (−)-Epicatechin into 3,4-Dihydroxyflavan Derivatives by the Endophytic Fungus Diaporthe sp. Isolated from a Tea Plant

Hirotaka SHIBUYA,^*,a Andria AGUSTA,^a Kazuyoshi OHASHI,^a Shoji MAEHARA,^a and Partomuan SIMANJUNTAK^b

^a Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University; Sanzo, 1 Gakuen-cho, Fukuyama, Hiroshima 729-0292, Japan: and ^b Research Centre for Biotechnology, Indonesian Institute of Sciences; Jalan Raya Bogor Km 46, Cibinong, Bogor 16911, Indonesia. * To whom correspondence should be addressed. e-mail: shibuya@fupharm.fukuyama-u.ac.jp

The microbial transformation of (+)-catechin (1) and (−)-epicatechin (2) by endophytic fungi isolated from a tea plant was investigated. It was found that the endophytic filamentous fungus Diaporthe sp. transformed them (1, 2) into the 3,4-cis-dihydroxyflavan derivatives, (+)-(2R,3S,4S)-3,4,5,7,3′,4′-hexahydroxyflavan (3) and (−)-(2R,3R,4R)-3,4,5,7,3′,4′-hexahydroxyflavan (7), respectively, whereas (−)-catechin (ent-1) and (+)-epicatechin (ent-2) with a 2S-phenyl group resisted the biooxidation.

Key words microbial transformation; (+)-catechin; (−)-epicatechin; endophyte; Diaporthe sp.; tea plant