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.
Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano 399-4598, Japan.
Takashi
T
Iijima
Yoshihiro
Y
Mohri
Yasunao
Y
Hattori
Atsushi
A
Kashima
Tsunashi
T
Kamo
Mitsuru
M
Hirota
Hiromasa
H
Kiyota
Hidefumi
H
Makabe
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002392:Catechin / Q000737:chemistry*; D005707:Gallic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D013237:Stereoisomerism
D000893:Anti-Inflammatory Agents; C541290:epicatechin 3-(3-O-methylgallate); D005707:Gallic Acid; C025525:3-O-methylgallic acid; D002392:Catechin