Reduction of testosterone, androstendione and their derivatives by Aphanocladium album
- 10 January 1989
- journal article
- research article
- Published by Wiley in Journal of Basic Microbiology
- Vol. 29 (1) , 1-12
- https://doi.org/10.1002/jobm.3620290102
Abstract
A strain of Aphanocladium album reduces the C‐3 carbonyl group in testosterone or androstendione to to 3α‐allyl alcohol. In some derivatives of these steroids the same carbonyl group is reduced to allyl alcohol with stereospecificity, depending on whether chlorine at C‐4 or a 17α‐methyl group is present. On the other hand, the presence of C‐4 methyl group, a C‐19 hydroxy group, a C‐17 acetyl one, or a double bond conjugated with the 4‐en‐3‐ ketone system totally inhibits the formation of allyl alcohols at C‐3.At the samé time, the C‐17 carbonyl group in androstendione or in its derivatives is reduced to a respective 17β‐alcohol.In the derivatives with an additional 2‐exomethylene group the double bond at this group is reduced.This publication has 11 references indexed in Scilit:
- Enantiospecific hydrolysis of acetates of racemic monoterpenic alcohols by Spirodela oligorrhizaPhytochemistry, 1988
- Conversion of Androstenedione to 3β-Hydroxy-5-Androsten-17-One and 3β-Hydroxy-4-Androsten-17-One by the Testicular Microsomal Fraction of Sprague-Dawley Rats1The Journal of Biochemistry, 1987
- The ability of Aphanocladium album and Rhodotorula mucilaginosa to transform some compounds of juvenoid typeJournal of Basic Microbiology, 1987
- Ileal metabolism in vitro of testosterone to 4-androstene-3α,17β-diolThe Journal of Steroid Biochemistry and Molecular Biology, 1983
- In vitro metabolism of testosterone to 17ß-hydroxy-5α-androstane-3-one and 5α-androstane-3α, 17ß-diol by the rat intestineThe Journal of Steroid Biochemistry and Molecular Biology, 1982
- Novel epimerizatton of steroidal allylic alcoholsSteroids, 1979
- The transformation of testosterone by Tetrahymena pyriformisThe Journal of Steroid Biochemistry and Molecular Biology, 1976
- Studies on the Metabolism of Steroids in the FoetusEuropean Journal of Biochemistry, 1970
- Kinetics of the Oxidation of Allyl Alcohols with Dichlorodicyanoquinone. Conformational and Isotope EffectsJournal of the American Chemical Society, 1964
- Electronic control of enzymatic oxidation-reduction processes. The reduction of Δ4-3-ketosteroids to Δ4-3-ols by the 3α- and 3β-hydroxysteroid dehydrogenases of pseudomonas testosteroniBiochemical and Biophysical Research Communications, 1963