Biotransformation XLVII: transformations of 5-ene steroids in Fusarium culmorum culture.
The course of the transformation of six 5-ene steroids with varying substituents at C-17 or/and C-3: dehydroepiandrosterone (DHEA), 5-androsten-3beta,17beta-diol, 17alpha-methyl-5-androsten-3beta,17beta-diol, 5-androsten-17-one, 5-androsten-3beta-ol and pregnenolone by Fusarium culmorum was investigated. Three substrates with oxygen functions at C-3 and C-17 i.e. DHEA, 5-androsten-3beta,17beta-diol and 17alpha-methyl-5-androsten-3beta,17beta-diol were hydroxylated entirely at 7alpha-axial, allylic position. The mixture of 7alpha-hydroxy- and 7alpha,15alpha-dihydroxyderivatives was formed during the transformation of pregnenolone and 5-androsten-17-one, from the latter 2alpha,7alpha-dihydroxyderivative was also obtained. 7alpha,15alpha- Dihydroxyderivative was the only product isolated from the 5-androsten-3beta-ol post-transformation mixture. The time-course of the DHEA transformation by F. culmorum shows that the substrate induces 7alpha-hydroxylase activity. DHEA was transformed by androstenedione induced F. culmorum cultures to a larger extent than by a noninduced microorganism; the selectivity of the transformation remained unchanged.
Kołek
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Department of Chemistry, Agricultural University, Wrocław, Poland.
D000735:Androstenedione / Q000378:metabolism; D000737:Androstenols / Q000493:pharmacokinetics; D001711:Biotransformation; D002849:Chromatography, Gas / Q000379:methods; D003687:Dehydroepiandrosterone / Q000378:metabolism / Q000493:pharmacokinetics; D005670:Fusarium / Q000378:metabolism*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D011284:Pregnenolone / Q000493:pharmacokinetics; D013256:Steroids / Q000378:metabolism / Q000493:pharmacokinetics*
D000737:Androstenols; D013256:Steroids; C034744:androst-5-en-3-ol; D000735:Androstenedione; D003687:Dehydroepiandrosterone; D011284:Pregnenolone