Synthesis of (-)-Epicatechin 3-(3-O-Methylgailate) and (+)-Catechin 3-(3-O- Methylgallate), and Their Anti-Inflammatory Activity

被引：12

作者：

Iijima, Takashi ^{[1
]}

Mohri, Yoshihiro ^{[1
]}

Hattori, Yasunao ^{[2
,3
]}

Kashima, Atsushi ^{[4
]}

Kamo, Tsunashi ^{[4
]}

Hirota, Mitsuru ^{[4
]}

Kiyota, Hiromasa ^{[5
]}

Makabe, Hidefumi ^{[1
]}

机构：

[1] Shinshu Univ, Grad Sch Agr, Nagano 3994598, Japan

[2] Shinshu Univ, Interdisciplinary Grad Sch Sci & Technol, Nagano 3994598, Japan

[3] Shinshu Univ, Satellite Venture Business Lab, Nagano 3868567, Japan

[4] Shinshu Univ, Fac Agr, Dept Biosci & Biotechnol, Nagano 3994598, Japan

[5] Tohoku Univ, Grad Sch Agr Sci, Dept Appl Bioorgan Chem, Div Biosci & Biotechnol Future Bioind,Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

CHEMISTRY & BIODIVERSITY | 2009年 / 6卷 / 04期

关键词：

MAST-CELLS; TEA; DERIVATIVES; INHIBITORS; CATECHINS; TANNINS; ACID;

D O I：

10.1002/cbdv.200800224

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 I and 2 suppressed the TPA-induced inflammation of mouse ears by 50 and 43%, respectively, at a dose of 200 mu g. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents.

引用

页码：520 / 526

页数：7

共 16 条

[1] Synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine derivatives: The central amino acid of vancomycin and related agents [J].