Abstract
The phenolic constituents of lahpet-so, a traditional postfermented tea of Myanmar produced under anaerobic conditions, were examined. The major polyphenols were identified to be pyrogallol and 4′-hydroxyphenyl-3-(2′′,4′′,6′′-trihydroxyphenyl)-propan-2-ol, 3′,4′-dihydroxyphenyl-3-(2′′,4′′,6′′-trihydroxyphenyl)-propan-2-ol, and 3′,4′,5′-trihydroxyphenyl-3-(2′′,4′′,6′′-trihydroxyphenyl)-propan-2-ol. The hydroxydiphenylpropan-2-ols were identical to the initial metabolites produced from green tea catechins by mammalian intestinal bacteria. In addition, an anaerobic mixed-fermentation experiment using lahpet-so and Japanese commercial green tea afforded two new catechin degradation products together with known compound bruguierol B and the above-mentioned catechin metabolites. Based on spectroscopic evidence, the structures of the new compounds were concluded to be 4-(2,5-dihydroxyhexyl)benzene-1,2-diol and (5S,8R)-6,7,8,9-tetrahydro-5-methyl-5·8-epoxy-5H-benzocycloheptene-2,3,4-triol. Interestingly, the production mechanism was deduced to be the inverse of the biosynthesis of the flavan-3-ol A ring.
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Acknowledgments
The authors are grateful to Mr. K. Inada and Mr. N. Tsuda (Nagasaki University) for NMR and MS measurements, and to Dr. Y. Miyata, Nagasaki Prefectural Agricultural and Forestry Experiment Station, Higashisonogi Tea Branch, for supplying green tea.
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Shii, T., Asada, C., Matsuo, Y. et al. Polyphenols in lahpet-so and two new catechin metabolites produced by anaerobic microbial fermentation of green tea. J Nat Med 68, 459–464 (2014). https://doi.org/10.1007/s11418-014-0816-1
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DOI: https://doi.org/10.1007/s11418-014-0816-1