Accumulation of epigallocatechin quinone dimers during tea fermentation and formation of theasinensins.
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.
Tanaka
Takashi
T
Department of Molecular Medicinal Sciences, Graduate School of Biomedical Sciences, Nagasaki University, Bunkyo Machi 1-14, Nagasaki 852-8521, Japan.
Mine
Chie
C
Watarumi
Sayaka
S
Fujioka
Toshihiro
T
Mihashi
Kunihide
K
Zhang
Ying-Jun
YJ
Kouno
Isao
I
D028241:Camellia sinensis / Q000737:chemistry*; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D005285:Fermentation; D006868:Hydrolysis; D007564:Japan; D008745:Methylation; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010619:Phenazines / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D011809:Quinones / Q000737:chemistry / Q000378:metabolism; D013662:Tea / Q000737:chemistry* / Q000378:metabolism*
D010619:Phenazines; D011809:Quinones; D013662:Tea; D002392:Catechin; C057580:gallocatechol