PMID: 11902970Mar 21, 2002Paper

Synthesis of theaflavin from epicatechin and epigallocatechin by plant homogenates and role of epicatechin quinone in the synthesis and degradation of theaflavin

Journal of Agricultural and Food Chemistry
Takashi TanakaI Kouno

Abstract

Oxidation products of (-)-epicatechin and (-)-epigallocatechin by treatment with homogenates of 62 plants belonging to 49 families were compared. Forty-six plants were capable of synthesizing theaflavin, a black tea pigment, regardless of whether they contained catechins. Loquat, Japanese pear, and blueberry had activities higher than that of fresh tea leaves after 5 h of treatment; furthermore, these plants oxidized theaflavin to theanaphthoquinone. An additional new metabolite, dehydrotheasinensin, was generated on treatment with fresh tea leaves, eggplant, and unripened Japanese orange. Evidence for the oxidation of epigallocatechin and theaflavin by electron transfer to epicatechin quinone was demonstrated in a time course study using bananas and trapping the quinone intermediates as glutathione conjugates.

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Citations

Jan 16, 2004·Bioorganic & Medicinal Chemistry·Shengmin SangChi-Tang Ho
Aug 7, 2012·Journal of Agricultural and Food Chemistry·Maria Nikolantonaki, Andrew L Waterhouse
Dec 3, 2005·Natural Product Research·Takashi TanakaIsao Kouno
Dec 4, 2004·Biological & Pharmaceutical Bulletin·Toshitsugu TaguriIsao Kouno
Dec 7, 2007·Chemical & Pharmaceutical Bulletin·Rie KusanoIsao Kouno
Mar 4, 2008·Chemical & Pharmaceutical Bulletin·Rie KusanoIsao Kouno
Aug 2, 2008·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Takashi Tanaka
Feb 18, 2010·International Journal of Molecular Sciences·Takashi TanakaIsao Kouno
Dec 23, 2015·Journal of Natural Products·Yosuke MatsuoTakashi Tanaka
Nov 26, 2015·Food Chemistry·Annewieke J W VerloopJean-Paul Vincken
Mar 15, 2015·Food Chemistry·Ghada H YassinNikolai Kuhnert
Jul 7, 2016·Journal of Agricultural and Food Chemistry·Annewieke J W VerloopJean-Paul Vincken
Feb 6, 2008·Natural Product Reports·Ronald Bentley
Apr 17, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Masumi Takemoto, Hiroaki Takemoto
Feb 25, 2010·Natural Product Reports·James Warren DrynanNikolai Kuhnert
Jan 13, 2011·Angewandte Chemie·Stéphane QuideauLaurent Pouységu
Jul 1, 2016·Journal of Food and Drug Analysis·Shu-Yen LinPo-An Chen
Jun 12, 2020·Frontiers in Chemistry·José A SoutoÁngel R de Lera
Jul 26, 2017·Angewandte Chemie·Yosuke MatsuoTakashi Tanaka
Dec 4, 2020·Chemical & Pharmaceutical Bulletin·Takashi Tanaka, Yosuke Matsuo
Jul 10, 2009·Organic Letters·A Ulises AcuñaBenjamín Rodríguez
Jul 16, 2009·Journal of Agricultural and Food Chemistry·Nicole KrafczykMarcus A Glomb
Dec 18, 2009·Journal of Natural Products·Yan LiIsao Kouno
Feb 1, 2020·Journal of Natural Products·Hatsumi WakamatsuTakashi Tanaka
Nov 18, 2020·Journal of Natural Products·Daisetsu KojimaGen-Ichiro Nonaka

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