Transformations of steroid esters by Fusarium culmorum.
The course of transformations of the pharmacological steroids: testosterone propionate, 4-chlorotestosterone acetate, 17beta-estradiol diacetate and their parent alcohols in Fusarium culmorum AM282 culture was compared. The results show that this microorganism is capable of regioselective hydrolysis of ester bonds. Only 4-ene-3-oxo steroid esters were hydrolyzed at C-17. 17beta-Estradiol diacetate underwent regioselective hydrolysis at C-3 and as a result, estrone--the main metabolite of estradiol--was absent in the reaction mixture. The alcohols resulting from the hydrolysis underwent oxidation at C-17 and hydroxylation. The same products (6beta- and 15alpha-hydroxy derivatives) as from testosterone were formed by transformation of testosterone propionate, but the quantitative composition of the mixtures obtained after transformations of both substrates showed differences. The 15alpha-hydroxy derivatives were obtained from the ester in considerably higher yield than from the parent alcohol. The presence of the chlorine atom at C-4 markedly reduced 17beta-saponification in 4-chlorotestosterone acetate. Only 3beta,15alpha-dihydroxy-4alpha-chloro-5alpha-androstan-17-one (the main product of transformation of 4-chlorotestosterone) was identified in the reaction mixture. 6beta-Hydroxy-4-chloroandrostenedione, which was formed from 4-chlorotestosterone, was not detected in the extract obtained after conversion of its ester.
Swizdor
Alina
A
Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland. alina@ozi.ar.wroc.pl
Kołek
Teresa
T
Szpineter
Anna
A
D001711:Biotransformation; D004958:Estradiol / Q000031:analogs & derivatives* / Q000378:metabolism*; D005670:Fusarium / Q000254:growth & development / Q000378:metabolism*; D013256:Steroids / Q000378:metabolism*; D013739:Testosterone / Q000031:analogs & derivatives / Q000378:metabolism; D043343:Testosterone Propionate / Q000378:metabolism*
D013256:Steroids; C053380:estradiol-3,17-diacetate; D013739:Testosterone; D004958:Estradiol; D043343:Testosterone Propionate