Polyphenols in lahpet-so and two new catechin metabolites produced by anaerobic microbial fermentation of green tea
Polyphenols in lahpet-so and two new catechin metabolites produced by anaerobic microbial fermentation of green tea
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lahpet-so中的多酚和绿茶厌氧微生物发酵产生的两种新的儿茶素代谢物
DOI：
10.1007/s11418-014-0816-1
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发表时间：
2014
影响因子：
3.3
通讯作者：
Takashi Tanaka
中科院分区：
文献类型：
--
作者：
Takuya Shii;Chiori Asada;Yosuke Matsuo;Yoshinori Saito;Takashi Tanaka
对 lahpet-so 的酚类成分进行了检测，lahpet-so 是一种在厌氧条件下生产的缅甸传统后发酵茶。主要多酚被鉴定为连苯三酚和4'-羟基苯基-3-(2'',4'',6''-三羟基苯基)-丙-2-醇、3',4'-二羟基苯基-3-(2'',4'',6''-三羟基苯基)-丙-2-醇和3',4',5'-三羟基苯基-3-(2'',4'',6''-三羟基苯基)-丙-2-醇。羟基二苯基丙-2-醇与哺乳动物肠道细菌从绿茶儿茶素产生的初始代谢物相同。此外，使用lahpet-so和日本商品绿茶进行厌氧混合发酵实验，与已知化合物bruguierol B和上述儿茶素代谢物一起提供了两种新的儿茶素降解产物。基于光谱证据，新化合物的结构被推断为4-(2,5-二羟基己基)苯-1,2-二醇和(5S,8R)-6,7,8,9-四氢-5-甲基-5·8-环氧-5H-苯并环庚烯-2,3,4-三醇。有趣的是，生产机制被推断为黄烷-3-醇A环生物合成的逆过程。
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.