Microbial transformation of beta-sitosterol and stigmasterol into 26-oxygenated derivatives.
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.
Ambrus
G
G
Institute for Drug Research, Budapest, Hungary.
Ilköy
E
E
Jekkel
A
A
Horváth
G
G
Böcskei
Z
Z
D013058:Mass Spectrometry; D015394:Molecular Structure; D009161:Mycobacterium / Q000235:genetics / Q000378:metabolism*; D010084:Oxidation-Reduction; D012855:Sitosterols / Q000737:chemistry / Q000378:metabolism*; D013265:Stigmasterol / Q000737:chemistry / Q000378:metabolism*; D014169:Transformation, Bacterial; D014961:X-Ray Diffraction
D012855:Sitosterols; C025473:gamma-sitosterol; D013265:Stigmasterol