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植物ポリフェノールの立体構造及び酸化機構解析への計算化学の適用


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Title: 植物ポリフェノールの立体構造及び酸化機構解析への計算化学の適用
Other Titles: Study of the Stereochemistry and Oxidation Mechanism of Plant Polyphenols, Assisted by Computational Chemistry
Authors: 松尾, 洋介
Authors (alternative): Matsuo, Yosuke
Issue Date: 1-Mar-2017
Publisher: 日本薬学会 / Pharmaceutical Society of Japan
Citation: YAKUGAKU ZASSHI, 137(3), pp.347-354; 2017
Abstract: In recent years, plant polyphenols have attracted great attention due to their wide range of biological activities. Certain kinds of polyphenols have complex structures; therefore, it is difficult to elucidate their total structure, including stereochemistry. In this study, we reinvestigated the stereostructures of two major C-glycosidic ellagitannins contained in Quercus plants, vescalagin and castalagin, and revised their stereostructures based on theoretical calculations of spectroscopic data. We also determined the structures of quercusnins A and B, isolated from the sapwood of Quercus crispula, based on theoretical calculations of NMR data. The oxidation mechanism of polyphenols has not been entirely elucidated. Therefore, we have also studied the oxidation mechanism of tea catechins during black tea production. Our investigation of the oxidation mechanism of black tea pigment theafiavins revealed that the difference in the position of the galloyl ester affords different oxidation products of theafiavins. In addition, oxidation products of pyrogallol-type catechins could be classified into three types-dehydrotheasinensins, theacitrins, and proepitheafiagallins; their detailed production and degradation mechanisms were also examined.
Keywords: Black tea / Catechin / Oxidative coupling / Polyphenol / Stereochemistry
URI: http://hdl.handle.net/10069/37448
ISSN: 00316903
DOI: 10.1248/yakushi.16-00207
Rights: © 2017 The Pharmaceutical Society of Japan.
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/37448

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