A new mechanism for oxidation of epigallocatechin and production of benzotropolone pigments

被引：65

作者：

Matsuo, Y ^{[1
]}

Tanaka, T ^{[1
]}

Kouno, I ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 20期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/j.tet.2006.03.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enzymatic oxidation of (-)-epigallocatechin gave two new quinone dimers, dehydrotheasinensin C and proepitheaflagallin. Dehydrotheasinensin C has a hydrated cyclohexenetrione structure and its oxidation-reduction dismutation reaction yielded black tea polyphenols, theasinensins C and E, and desgalloyl oolongtheanin. The structure of proepitheaflagallin was determined based on spectroscopic data of its quinoxaline derivatives prepared by condensation with o-phenylenediamine. Proepitheaflagallin was decomposed on heating to give epitheaflagallin and hydroxytheaflavin. The former is a known black tea pigment and the latter is a new pigment with 1',2,3'-trihydroxy-3,4-benzotropolone moiety. The results revealed a new mechanism for the production of these pigments from epigallocatechin. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4774 / 4783

页数：10

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