P-69 紅茶ポリフェノールの生成機構 : カテキン酸化カスケード(ポスター発表の部)
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概要
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Enzymatic oxidation of epigallocatechin and its gallate, as a model of fermentation process of black tea production, provided valuable information on catechin oxidation. Coupling of B-ring o-quinones afforded dehydrotheasinensin A, a quinone dimer having hydrated triketone structure, which undergo oxidation-reduction dismutation to yield theasinensins and oolongtheanins. We have now succeeded to show production of analogous catechin trimers having two hydrated triketone moieties produced by oxidative coupling between a galloyl group of dehydrotheasinensin A and epigallocatechin B-ring. It is presumed that dismutation reaction of the trimers affords complex mixtures of dismutation products and it may explain the complexity of black tea polyphenols. In addition, new formation mechanism of benzotropolone pigments was disclosed. In the mechanism, oxidative condensation between two pyrogallol B-rings gave an unstable compound having hydrated bicyclo[5,4,0]undeca-1,2,7,8,9-pentaoxo-3-ene moiety. On heating, the compound converted to epitheaflagallin and hydroxytheaflavin, which are known and new benzotropolone pigments, respectively. Furthermore, a novel quinone dimer of epigallocatechin-3-O-gallate was isolated, which have a caged structure formed by successive aldol-type C-C bond formation between two B-ring o-quinones.
- 天然有機化合物討論会の論文
- 2005-09-15
著者
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田中 隆
長崎大学大学院医歯薬学総合研究科
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河野 功
長崎大学大学院医歯薬学総合研究科
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松尾 洋介
長崎大学大学院医歯薬学総合研究科
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松尾 洋介
長崎大院医歯薬
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李 岩
長崎大院医歯薬
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田中 隆
長崎大院医歯薬
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河野 功
長崎大院医歯薬
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Matsuo Yosuke
Graduate School Of Biomedical Sciences Nagasaki Univ.
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Kouno Isao
Faculty Of Pharmaceutical Sciences Nagasaki University
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Tanaka Tomonori
Faculty Of Medical And Pharmaceutical Sciences Kumamoto University
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田中 隆
Faculty Of Pharmaceutical Sciences Kyushu University
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Tanaka Takemi
School Of Agriculture Kyushu Tokai University
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