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


BACKGROUND
Green tea; catechins; (-)-EGCG O-acyl derivatives; antitumor activity.
Vyas
Sandeep
S
University Institute of Pharmaceutical Sciences and Department of Chemistry, Panjab University, Chandigarh 160014, India.
Sharma
Manu
M
Sharma
Pritam D
PD
Singh
Tej V
TV
D015127:9,10-Dimethyl-1,2-benzanthracene; D000215:Acylation; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000627:therapeutic use*; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000627:therapeutic use; D051379:Mice; D009374:Neoplasms, Experimental / Q000139:chemically induced / Q000188:drug therapy*; D013662:Tea / Q000737:chemistry*; D013755:Tetradecanoylphorbol Acetate
D000972:Antineoplastic Agents, Phytogenic; D013662:Tea; D015127:9,10-Dimethyl-1,2-benzanthracene; D002392:Catechin; C045651:epigallocatechin gallate; D013755:Tetradecanoylphorbol Acetate