Accumulation of Epigallocatechin Quinone Dimers during Tea Fermentation and Formation of Theasinensins

• Published in: Journal of natural products (Washington, D.C.) Vol. 65; no. 11; pp. 1582 - 1587
• Main Authors: Tanaka, Takashi, Mine, Chie, Watarumi, Sayaka, Fujioka, Toshihiro, Mihashi, Kunihide, Zhang, Ying-Jun, Kouno, Isao
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.2002; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Biological and medical sciences; Camellia sinensis - chemistry; Catechin - analogs & derivatives; Catechin - chemistry; Catechin - isolation & purification; Catechin - metabolism; Chemistry, Medicinal; Chromatography, High Pressure Liquid; Coffee, tea and other stimulative beverage industries; Fermentation; Food industries; Fundamental and applied biological sciences. Psychology; General pharmacology; Hydrolysis; Japan; Life Sciences & Biomedicine; Medical sciences; Methylation; Molecular Conformation; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oxidation-Reduction; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Phenazines - chemistry; Plant Leaves - chemistry; Plant Sciences; Plants, Medicinal - chemistry; Quinones - chemistry; Quinones - metabolism; Science & Technology; Tea - chemistry; Tea - metabolism; PRODUCTS; LEAF; TANNINS; Catechin; Reaction product; Quinone; Plant leaf; Fermentation; Flavonoid; Phenazine derivatives; Phenylenediamine; Tea; Camellia sinensis; Polyphenol; Tannin; Dicotyledones; Angiospermae; Spermatophyta; Dimer; Oxidation; Theaceae
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np020245k

Production and accumulation of catechin dimer quinones during tea fermentation were chemically confirmed for the first time by trapping as phenazine derivatives. Direct treatment of the fermented tea leaves with o-phenylenediamine yielded five phenazine derivatives (8−12) of o-quinones of an epigallocatechin dimer and its galloyl esters (13−16), in which two flavan units were linked at the B-rings through a C−C bond. Atrop isomerism of the biphenyl bonds was shown to be the R configuration, suggesting that the o-quinone dimers were generated by stereoselective coupling of monomeric quinones. The total concentration of the phenazine derivatives in the o-phenylenediamine-treated tea leaves was higher than that of theaflavins. In contrast, phenazine derivatives of monomeric quinones of epigallocatechin were not isolated. When the fermented tea leaves were heated, the quinone dimers were converted to theasinensins, which are constituents of black tea, suggesting that theasinensins are generated by reduction of the quinone dimers during the heating and drying steps in black tea manufacturing.