MICROBIAL TRANSFORMATION OF BETA-SITOSTEROL AND STIGMASTEROL INTO 26-OXYGENATED DERIVATIVES

被引:15
作者
AMBRUS, G [1 ]
ILKOY, E [1 ]
JEKKEL, A [1 ]
HORVATH, G [1 ]
BOCSKEI, Z [1 ]
机构
[1] CHINOIN PHARMACEUT,BUDAPEST,HUNGARY
关键词
BETA-SITOSTEROL; MICROBIAL SIDE CHAIN DEGRADATION; MECHANISM OF C-26-OXIDATION;
D O I
10.1016/0039-128X(95)00077-4
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
引用
收藏
页码:621 / 625
页数:5
相关论文
共 17 条
[1]   HYDROGENATION OF UNSATURATED STEROID RING SYSTEMS WITH MYCOBACTERIUM PHLEI [J].
AMBRUS, G ;
TOMORKENY, E ;
BUKI, KG .
EXPERIENTIA, 1968, 24 (05) :432-+
[2]   NOVEL INTERMEDIATES OF MICROBIAL SIDE-CHAIN DEGRADATION OF SITOSTEROL [J].
AMBRUS, G ;
ILKOY, E ;
HORVATH, G ;
PODANYI, B ;
BOCSKEI, Z ;
GYURKY, S ;
JEKKEL, A .
TETRAHEDRON LETTERS, 1992, 33 (36) :5267-5268
[3]   MICROBIAL-DEGRADATION OF THE PHYTOSTEROL SIDE-CHAIN .2. INCORPORATION OF NAHC-14O3 ONTO THE C-28 POSITION [J].
FUJIMOTO, Y ;
CHEN, CS ;
GOPALAN, AS ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4720-4722
[4]   MICROBIAL-DEGRADATION OF THE PHYTOSTEROL SIDE-CHAIN .1. ENZYMATIC CONVERSION OF 3-OXO-24-ETHYLCHOLEST-4-EN-26-OIC ACID INTO 3-OXOCHOL-4-EN-24-OIC ACID AND ANDROST-4-ENE-3,17-DIONE [J].
FUJIMOTO, Y ;
CHEN, CS ;
SZELECZKY, Z ;
DITULLIO, D ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4718-4720
[5]  
HAYASHI S, 1969, CHEM PHARM BULL, V17, P163
[6]  
HORVATH G, 1991, 4TH P S AN STER PECS, P277
[7]  
HORVATH G, 1994, 5TH P S AN STER SZOM, P301
[8]  
JEKKEL A, 1989, J GEN MICROBIOL, V135, P1727
[9]   CONSTITUENTS FROM KIDNEY BEAN .1. PHYTOSTEROLS AND TRITERPENES IN ROOTS OF KIDNEY BEAN (PHASEOLUS-VULGARIS L) [J].
KATSUI, N ;
HIRATA, T ;
MATSUE, H ;
MASAMUNE, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (01) :223-+
[10]   MICROBIOLOGICAL TRANSFORMATIONS OF BETA-SITOSTEROL AND STIGMASTEROL BY A SOIL PSEUDOMONAD [J].
MAHATO, SB ;
BANERJEE, S .
EXPERIENTIA, 1980, 36 (05) :515-516