Microbial conversion of androst-1,4-dien-3,17-dione by Mucor racemosus to hydroxysteroid-1,4-dien-3-one derivatives
BACKGROUND: A large number of bacterial, fungal and microalgal species are able to bio-transform steroid compounds. Among them, fungi from the Mucor genus have been shown to mediate hydroxylation, oxidation, and desaturation by the double bond formation and epoxidation of various steroid substances....
Gespeichert in:
Veröffentlicht in: | Journal of chemical technology and biotechnology (1986) 2009-07, Vol.84 (7), p.1021-1025 |
---|---|
Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | BACKGROUND: A large number of bacterial, fungal and microalgal species are able to bio-transform steroid compounds. Among them, fungi from the Mucor genus have been shown to mediate hydroxylation, oxidation, and desaturation by the double bond formation and epoxidation of various steroid substances. Mucor racemocus has not been studied for its ability to modify androst-1,4-dien-3,17-dione, a pharmaceutically important steroid precursor.RESULTS: The filamentous fungus M. racemosus was applied for bioconversion of androst-1,4-dien-3,17-dione (ADD, I) in a 5-day fermentation. Microbial metabolites were purified chromatographically and identified on the basis of their spectral data as 17β-hydroxyandrost-1,4-dien-3-one (II), 14α-hydroxyandrost-1,4-dien-3,17-dione (III), 15α-hydroxyandrost-1,4-dien-3,17-dione (IV), 15α,17β-dihydroxyandrost-1,4-dien-3-one (V), 14α,17β-dihydroxyandrost-1,4-dien-3-one (VI), and 6β,17β-dihydroxyandrost-1,4-dien-3-one (VII).CONCLUSION: Observed modifications included hydroxylation at C-6β, C-14α, C-15α positions and 17-carbonyl reduction. The best fermentation conditions for production of hydroxysteroid-1,4-dien-3-one derivatives were found to be 25 °C at 150 rpm for 5 days with a substrate concentration of 0.5 g L⁻¹. Copyright |
---|---|
ISSN: | 0268-2575 1097-4660 1097-4660 |
DOI: | 10.1002/jctb.2128 |