Synthesis of epigallocatechin trimer, (epigallocatechin)2-epicatechin, and (epigallocatechin)2-catechin via a Lewis acid mediated one-pot condensation and their antitumor activities in prostate cancer cells

被引：3

作者：

Ichikawa, Mikihiro ^{[1
]}

Yamamoto, Shinya ^{[2
]}

Ishihara, Chisato ^{[3
]}

Nonobe, Shuhei ^{[3
]}

Hattori, Yasunao ^{[4
]}

Umezawa, Koji ^{[3
,5
]}

Fujii, Hiroshi ^{[3
,5
]}

Makabe, Hidefumi ^{[1
,2
,5
]}

机构：

[1] Shinshu Univ, Grad Sch Agr Sci Funct Foods, 8304 Minami Minowa Kami Ina, Nagano 3994598, Japan

[2] Shinshu Univ, Grad Sch Sci & Technol, Dept Agr, Div Food Sci & Biotechnol, 8304 Minami Minowa Kami Ina, Nagano 3994598, Japan

[3] Shinshu Univ, Grad Sch Sci & Technol, Dept Biomed Engn, 8304 Minami Minowa Kami Ina, Nagano 3994598, Japan

[4] Kyoto Pharmaceut Univ, Ctr Instrumental Anal, Yamashina Ku, Kyoto 6078412, Japan

[5] Shinshu Univ, Dept Interdisciplinary Cluster Cutting Edge Res, 8304 Minami Minowa Kami Ina, Nagano 3994598, Japan

来源：

TETRAHEDRON | 2018年 / 74卷 / 27期

关键词：

Polyphenol; Condensation; Lewis acid; Proanthocyanidin; Antitumor; PROANTHOCYANIDINS; PROCYANIDINS; INHIBITION;

D O I：

10.1016/j.tet.2018.04.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of epigallocatechin trimer, (epigallocatechin)(2)-epicatechin and (epigallocatechin)(2)-catechin were achieved. The key condensation to form the proanthocyanidin trimer derivatives was accomplished in a one-pot procedure using a dimeric epigallocatechin electrophile, which was prepared in situ by self-condensation of an epigallocatechin derivative, and an epigallocatechin, epicatechin, or catechin derivative as the nucleophile in the presence of a Lewis acid. The epigallocatechin monomer to trimer compounds containing a pyrogallol group significantly suppressed cell proliferation in PC-3 prostate cancer cells. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3534 / 3542

页数：9

共 19 条

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