Synthesis of (-)-epicatechin 3-(3-O-methylgallate) and (+)-catechin 3-(3-O-methylgallate), and their anti-inflammatory activity.

A concise synthesis of (-)-epicatechin 3-(3-O-methylgallate) (1; ECG3''Me), which is a minor constituent of tea, and (+)-catechin 3-(3-O-methylgallate) (2; CG3''Me) via condensation of equimolar amount of catechin and gallate derivatives has been achieved. The anti-inflammatory effect of the synthetic compounds on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. Compounds 1 and 2 suppressed the TPA-induced inflammation of mouse ears by 50 and 43%, respectively, at a dose of 200 microg. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents.