Abstract
The course of the transformation of six 5-ene steroids with varying substituents at C-17 or/and C-3: dehydroepiandrosterone (DHEA), 5-androsten-3β,17β-diol, 17α-methyl-5-androsten-3β,17β-diol, 5-androsten-17-one, 5-androsten-3β-ol and pregnenolone by Fusarium culmorum was investigated. Three substrates with oxygen functions at C-3 and C-17 i.e. DHEA, 5-androsten-3β,17β-diol and 17α-methyl-5-androsten-3β,17β-diol were hydroxylated entirely at 7α-axial, allylic position. The mixture of 7α-hydroxy- and 7α,15α-dihydroxyderivatives was formed during the transformation of pregnenolone and 5-androsten-17-one, from the latter 2α,7α-dihydroxyderivative was also obtained. 7α,15α- Dihydroxyderivative was the only product isolated from the 5-androsten-3β-ol post-transformation mixture. The time-course of the DHEA transformation by F. culmorum shows that the substrate induces 7α-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.
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