Synthesis of Theaflavin from Epicatechin and Epigallocatechin by Plant Homogenates and Role of Epicatechin Quinone in the Synthesis and Degradation of Theaflavin

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...

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Published in:Journal of agricultural and food chemistry 2002-03, Vol.50 (7), p.2142-2148
Main Authors: Tanaka, Takashi, Mine, Chie, Inoue, Kyoko, Matsuda, Miyuki, Kouno, Isao
Format: Article
Language:English
Subjects:
Applied sciences
Biflavonoids
Biological and medical sciences
Catechin - analogs & derivatives
Catechin - metabolism
Exact sciences and technology
General pharmacology
Kinetics
Magnetic Resonance Spectroscopy
Medical sciences
Miscellaneous
Musa - metabolism
Natural polymers
Oxidation-Reduction
Pharmaceutical technology. Pharmaceutical industry
Pharmacology. Drug treatments
Physicochemistry of polymers
Plants - metabolism
Tea - chemistry
Tea - metabolism
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Summary: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. Keywords: Catechin; oxidation; theaflavin; dehydrotheasinensin; black tea; polyphenol
ISSN:0021-8561
1520-5118
DOI:10.1021/jf011301a