胆汁酸的微生物降解。由红色链霉菌从胆酸形成的含氮六氢茚衍生物。
Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens.
作者信息
Hayakawa S, Hashimoto S, Onaka T
出版信息
Biochem J. 1976 Dec 15;160(3):745-55. doi: 10.1042/bj1600745.
The metabolism of cholic acid (I) by Streptomyces rubescens was investigated. This organism effected ring A cleavage, side-chain shortening and amide bond formation and gave the following metabolites: (4R)-4-[4alpha-(2-carboxyethyl)-3aalpha-hexahydro-7abeta-methyl-5-oxoindan-1 beta-yl]valeric acid (IIa) and its mono-amide (valeramide) (IIb); and 2,3,4,6, 6abeta,7,8,9,9aalpha,9bbeta-decahydro-6abeta-methyl-1H-cyclopenta[f]quinoline-3,7-dione(IIIe)and its homologues with the beta-oriented side chains, valeric acid, valeramide, butanone and propionic acid, in the place of the oxo group at C-7, i.e.compounds (IIIa), (IIIb), (IIIc) and (IIId) respectively. All the nitrogenous metabolites were new compounds, and their structures were established by partial synthesis except for the metabolite (IIIc). The mechanism of formation of these metabolites is considered. A degradative pathway of cholic acid (I) into the metabolites is also tentatively proposed.
研究了红色链霉菌对胆酸（I）的代谢。该微生物实现了A环裂解、侧链缩短和酰胺键形成，并产生了以下代谢产物：(4R)-4-[4α-(2-羧乙基)-3aα-六氢-7aβ-甲基-5-氧代茚满-1β-基]戊酸（IIa）及其单酰胺（戊酰胺）（IIb）；以及2,3,4,6,6aβ,7,8,9,9aα,9bβ-十氢-6aβ-甲基-1H-环戊[f]喹啉-3,7-二酮（IIIe）及其在C-7位羰基被β-取向侧链、戊酸、戊酰胺、丁酮和丙酸取代的同系物，即分别为化合物（IIIa）、（IIIb）、（IIIc）和（IIId）。所有含氮代谢产物均为新化合物，除代谢产物（IIIc）外，其结构通过部分合成确定。考虑了这些代谢产物的形成机制。还初步提出了胆酸（I）降解为这些代谢产物的途径。
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