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Synthesis of (−)‐Epicatechin 3‐(3‐ O ‐Methylgallate) and (+)‐Catechin 3‐(3‐ O ‐Methylgallate), and Their Anti‐Inflammatory Activity
Author(s) -
Iijima Takashi,
Mohri Yoshihiro,
Hattori Yasunao,
Kashima Atsushi,
Kamo Tsunashi,
Hirota Mitsuru,
Kiyota Hiromasa,
Makabe Hidefumi
Publication year - 2009
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200800224
Subject(s) - catechin , chemistry , gallate , inflammation , anti inflammatory , stereochemistry , polyphenol , pharmacology , biochemistry , nuclear chemistry , antioxidant , immunology , medicine , biology
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.