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β-谷甾醇和豆甾醇向26-氧化衍生物的微生物转化

Microbial transformation of beta-sitosterol and stigmasterol into 26-oxygenated derivatives.

作者信息

Ambrus G, Ilköy E, Jekkel A, Horváth G, Böcskei Z

机构信息

Institute for Drug Research, Budapest, Hungary.

出版信息

Steroids. 1995 Sep;60(9):621-5. doi: 10.1016/0039-128x(95)00077-4.

DOI:10.1016/0039-128x(95)00077-4
PMID:8545851
Abstract

The genetically modified Mycobacterium sp. BCS 396 strain has been used to transform sterols with stigmastane side chain in order to obtain 26-oxidized metabolites. beta-Sitosterol (I) was transformed to 4-stigmasten-3-one (II), 26-hydroxy-4-stigmasten-3-one (III), and 3-oxo-4-stigmasten-26-oic acid (IV), while stigmasterol (V) was converted to 4,22-stigmastadien-3-one (VI), 6 beta-hydroxy-4,22-stigmastadien-3-one (VII), 26-hydroxy-4,22-stigmastadien-3-one (VIII), 3-oxo-4,22-stigmastadien-26-oic acid methyl ester (IX), and 3-oxo-1,4,22-stigmastatrien-26-oic acid methyl ester (X) with that strain. In both beta-sitosterol and stigmasterol, 26-oxidation generates the R-configuration on C-25.

摘要

转基因分枝杆菌属BCS 396菌株已被用于转化具有豆甾烷侧链的甾醇,以获得26-氧化代谢产物。β-谷甾醇(I)被转化为4-豆甾烯-3-酮(II)、26-羟基-4-豆甾烯-3-酮(III)和3-氧代-4-豆甾烯-26-酸(IV),而豆甾醇(V)则被该菌株转化为4,22-豆甾二烯-3-酮(VI)、6β-羟基-4,22-豆甾二烯-3-酮(VII)、26-羟基-4,22-豆甾二烯-3-酮(VIII)、3-氧代-4,22-豆甾二烯-26-酸甲酯(IX)和3-氧代-1,4,22-豆甾三烯-26-酸甲酯(X)。在β-谷甾醇和豆甾醇中,26-氧化在C-25上产生R-构型。

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