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