Transformations of 4- and 17alpha-substituted testosterone analogues by Fusarium culmorum.
A series of 4- and/or 17alpha-substituted testosterone analogues has been incubated with the hydroxylating fungus Fusarium culmorum AM282. It was found that 19-norandrostenedione, 19-nortestosterone, 4-methoxytestosterone, 4-methyltestosterone, and 4-chloro-17alpha-methyltestosterone were hydroxylated exclusively or mainly at the 6beta-position. The mixtures of 6beta-, 15alpha-, and 12beta- or 11alpha-monohydroxy derivatives were obtained from 17alpha-methyltestosterone and 17alpha-ethyl-19-nortestosterone--the substrates with alkyl group at C-17alpha. 4-Chlorotestosterone was predominantly hydroxylated at 15alpha-position, but the reaction was accompanied by the reduction of 4-en-3-one system, which proceeded in the sequence: reduction of ketone to 3beta-alcohol and then reduction of the double 4,5 bond. The results obtained indicate an influence of stereoelectronic and steric effects of substitutes on regioselectivity of the hydroxylation of 4-en-3-one steroids by F. culmorum.
Swizdor
Alina
A
Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland. alina@ozi.ar.wroc.pl
Kołek
Teresa
T
D001711:Biotransformation / Q000187:drug effects / Q000502:physiology; D004845:Epitestosterone / Q000031:analogs & derivatives / Q000378:metabolism* / Q000494:pharmacology; D005670:Fusarium / Q000502:physiology*; D006900:Hydroxylation / Q000187:drug effects
D004845:Epitestosterone