title: Biotransformation of (20S)-20-hydroxymethylpregna-1,4-dien-3-one by four filamentous fungi.
abstract: Microbial transformation of (20S)-20-hydroxymethylpregna-1,4-dien-3-one (1) by four filamentous fungi, Cunninghamella elegans, Macrophomina phaseolina, Rhizopus stolonifer, and Gibberella fujikuroi, afforded nine new, and two known metabolites 2-12. The structures of these metabolites were characterized through detailed spectroscopic analysis. These metabolites were obtained as a result of biohydroxylation of 1 at C-6β, -7β, -11α, -14α, -15β, -16β, and -17α positions, except metabolite 2 which contain an O-acetyl group at C-22. These fungal strains demonstrated to be efficient biocatalysts for 11α-hydroxylation. Compound 1, and its metabolites were evaluated for the first time for their cytotoxicity against the HeLa cancer cell lines, and some interesting results were obtained.
authors.affiliation: H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
authors.forename: M Iqbal
authors.initials: MI
authors.lastname: Choudhary
authors.forename: Saira
authors.initials: S
authors.lastname: Erum
authors.forename: Muhammad
authors.initials: M
authors.lastname: Atif
authors.forename: Rizwana
authors.initials: R
authors.lastname: Malik
authors.forename: Naik Tameen
authors.initials: NT
authors.lastname: Khan
authors.lastname: Atta-ur-Rahman
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001203:Ascomycota / Q000378:metabolism; D001711:Biotransformation; D020093:Cunninghamella / Q000378:metabolism; D005658:Fungi / Q000378:metabolism*; D005874:Gibberella / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D006900:Hydroxylation; D015394:Molecular Structure; D011245:Pregnadienes / Q000737:chemistry / Q000378:metabolism*; D012233:Rhizopus / Q000378:metabolism; D013057:Spectrum Analysis; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D011245:Pregnadienes