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

Takashi Iijima, Yoshihiro Mohri, Yasunao Hattori, Atsushi Kashima, Tsunashi Kamo, Mitsuru Hirota, Hiromasa Kiyota, Hidefumi Makabe

    Research output: Contribution to journalArticlepeer-review

    11 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)520-526
    Number of pages7
    JournalChemistry and Biodiversity
    Volume6
    Issue number4
    DOIs
    Publication statusPublished - 2009 May 26

    ASJC Scopus subject areas

    • Bioengineering
    • Biochemistry
    • Chemistry(all)
    • Molecular Medicine
    • Molecular Biology

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