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


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Title: Production mechanism of proepitheaflagallin, a precursor of benzotropolone-type black tea pigment, derived from epigallocatechin via a bicyclo[3.2.1]octane-type intermediate
Authors: Matsuo, Yosuke / Tanaka, Takashi / Kouno, Isao
Issue Date: 25-Mar-2009
Publisher: Elsevier BV
Citation: Tetrahedron Letters, 50(12), pp.1348-1351; 2009
Abstract: 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.
Keywords: Benzotropolone / Bicyclo[3.2.1]octane / Black tea / Enzymatic oxidation / Epigallocatechin / Proepitheaflagallin / Theaflavin
URI: http://hdl.handle.net/10069/20914
ISSN: 00404039
DOI: 10.1016/j.tetlet.2009.01.030
Rights: Copyright (c) 2009 Elsevier Ltd All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/20914

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