Design, semisynthesis, and evaluation of O-acyl derivatives of (-)-epigallocatechin-3-gallate as antitumor agents

J Agric Food Chem. 2007 Jul 25;55(15):6319-24. doi: 10.1021/jf070519f. Epub 2007 Jul 3.

Abstract

The partially purified catechin fraction isolated from green tea extract was treated with a variety of acylating agents (acyl anhydrides/chloride) to obtain (-)-epigallocatechin-3-gallate (EGCG) O-acyl derivatives in 20-25.4% yields. The (-)-EGCG O-acyl derivatives were characterized by physical data and spectral studies. These compounds were evaluated for their antitumor activity by use of a two-stage carcinogenesis model in 7,12-dimethylbenz[a]anthracene (DMBA)/12-O-tetradecanoylphorbol 13-acetate (TPA)--induced cancer in Swiss albino mice. The study showed that there was a significant decrease in the antitumor activity with the increase in size and branching of the chain length of acyl groups. The results indicated that these O-acyl derivatives of (-)-EGCG have the potential to be developed as cancer chemopreventive agents.

Keywords: Green tea; catechins; (-)-EGCG O-acyl derivatives; antitumor activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 9,10-Dimethyl-1,2-benzanthracene
  • Acylation
  • Animals
  • Antineoplastic Agents, Phytogenic / therapeutic use*
  • Catechin / analogs & derivatives*
  • Catechin / chemistry
  • Catechin / therapeutic use
  • Mice
  • Neoplasms, Experimental / chemically induced
  • Neoplasms, Experimental / drug therapy*
  • Tea / chemistry*
  • Tetradecanoylphorbol Acetate

Substances

  • Antineoplastic Agents, Phytogenic
  • Tea
  • 9,10-Dimethyl-1,2-benzanthracene
  • Catechin
  • epigallocatechin gallate
  • Tetradecanoylphorbol Acetate