Production mechanism of proepitheaflagallin, a precursor of benzotropolone-type black tea pigment, derived from epigallocatechin via a bicyclo[3.2.1]octane-type intermediate

TETRAHEDRON LETTERS

卷:50

Article

Matsuo, Yosuke¹  Tanaka, Takashi¹  Kouno, Isao¹ 

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

关键词: Black tea;    Epigallocatechin;    Enzymatic oxidation;    Proepitheaflagallin;    Benzotropolone;    Bicyclo[3.2.1]octane;    Theaflavin;   

DOI  :  10.1016/j.tetlet.2009.01.030

来源: Elsevier

【 摘 要 】

An unstable intermediate proepitheaflagallin B (2), a precursor of proepitheaflagallin (3), was isolated as an enzymatic oxidation product of (-)-epigallocatechin (1), and the structure of 2 was determined based on spectroscopic data. The structure and its decomposition revealed that the detailed production mechanism of proepitheaflagallin (3) via a bicyclo[3.2.1]octane-type intermediate was related to that of major black tea pigments. theaflavins. (c) 2009 Elsevier Ltd. All rights reserved.

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