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Paper | Regular issue | Vol 92, No. 10, 2016, pp.1822-1831
Published online, 6th September, 2016
DOI: 10.3987/COM-16-13557
Synthesis of Prodelphinidin Trimer Isolated from Cistus Albidus and its Growth Inhibitory Activity Against Human Prostate Cancer Cell Lines

Masataka Mori, Kiriko Matsumoto, Chisato Ishihara, Koichiro Kawaguchi, Sei-ichi Kawahara, Yasunao Hattori, Hiroshi Fujii,* and Hidefumi Makabe*

*Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minamiminowa-mura, Kamiina-gun, Nagano 399-4598, Japan

Abstract

First synthesis of prodelphinidin trimer (epigallocatechin-gallocatechin-catechin) isolated from Cistus albidus was accomplished from monomeric epigallocatechin electrophile and dimeric gallocatechin-catechin nucleophile. The condensation was worked using AgOTf as a Lewis acid and condensed product was successfully converted into titled compound in good yield. Synthesized compound showed significant growth inhibitory activity against human prostate PC-3 cell lines. Its activity was little bit stronger than that of prodelphinidin B3.