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 μg. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used anti‐inflammatory agents.