Design, Semisynthesis, and Evaluation of O-Acyl Derivatives of (−)-Epigallocatechin-3-gallate as Antitumor Agents

Sandeep Vyas,†‡ Manu Sharma,† Pritam D. Sharma,*† and Tej V. Singh‡
University Institute of Pharmaceutical Sciences and Department of Chemistry, Panjab University, Chandigarh 160014, India
J. Agric. Food Chem., 2007, 55 (15), pp 6319–6324
DOI: 10.1021/jf070519f
Publication Date (Web): July 3, 2007
Copyright © 2007 American Chemical Society
†

 University Institute of Pharmaceutical Sciences.

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‡

 Department of Chemistry.

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*

 Corresponding author:  tel +911722534117; fax +911722541142; e-mail pritamdevsharma@hotmail.com.

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

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History

  • Published In Issue July 25, 2007
  • Received for review February 22, 2007. Revised manuscript received May 14, 2007. Accepted May 24, 2007. We thank the Indian Council of Medical Research (ICMR), New Delhi, for financial support.

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