（-）-表没食子儿茶素-3-没食子酸酯的O-酰基衍生物作为抗肿瘤剂的设计、半合成及评估

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

作者信息

Vyas Sandeep, Sharma Manu, Sharma Pritam D, Singh Tej V

机构信息

University Institute of Pharmaceutical Sciences and Department of Chemistry, Panjab University, Chandigarh 160014, India.

出版信息

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

DOI:10.1021/jf070519f

PMID:17608429

Abstract

UNLABELLED

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.

摘要

未标记

从绿茶提取物中分离得到的部分纯化儿茶素组分，用多种酰化剂（酸酐/酰氯）处理，以20 - 25.4%的产率获得（-）-表没食子儿茶素-3-没食子酸酯（EGCG）的O-酰基衍生物。通过物理数据和光谱研究对（-）-EGCG的O-酰基衍生物进行了表征。利用二阶段致癌模型，在7,12-二甲基苯并[a]蒽（DMBA）/12-O-十四酰佛波醇-13-乙酸酯（TPA）诱导的瑞士白化小鼠癌症中，对这些化合物的抗肿瘤活性进行了评估。研究表明，随着酰基链长度的增加和支化程度的增大，抗肿瘤活性显著降低。结果表明，这些（-）-EGCG的O-酰基衍生物有潜力被开发为癌症化学预防剂。