Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities

  • Bioorg Med Chem Lett. 2013 Sep 1;23(17):4935-9. doi: 10.1016/j.bmcl.2013.06.061.
Manato Suda  1 ,  Miyuki Katoh ,  Kazuya Toda ,  Kiriko Matsumoto ,  Koichiro Kawaguchi ,  Sei-ichi Kawahara ,  Yasunao Hattori ,  Hiroshi Fujii ,  Hidefumi Makabe
Affiliations
  • 1. Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-Minowa Kami-Ina, Nagano 399-4598, Japan.
PMID: 23867167 DOI: 10.1016/j.bmcl.2013.06.061
Abstract

Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)3. Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3.

Keywords
Antitumor; Condensation; Lewis acid; Polyphenol; Procyanidin gallate.
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