Biotransformation of methyltestosterone by the filamentous fungus Mucor racemosus

Abstract

Fungi have proved to be powerful biocatalysts in steroid biotransformations. In the present study, the soil isolate filamentous fungus Mucor racemosus was applied for bioconversion of methyltestosterone (1), an anabolic steroid, in a five-day fermentation. Microbial metabolites were purified chromatographically and identified on the basis of their spectral data as 7D-hydroxymethyltestosterone (2), 15D-hydroxymethyltestosterone (3), and 12, 15D-dihydroxymethyltestosterone (4). Observed modifications were hydroxylations at C-7D, C-12, and 15D-positions. Best fermentation condition for production of hydroxylated derivatives was found to be 25qC at 150 rpm for 5 days with a substrate concentration of 1 mg/mL.

Studies on drug metabolism by fungi colonizing decomposing human cadavers. Part II: biotransformation of five model drugs by fungi isolated from post‐mortem material

“…[18][19][20][21] In vitro studies with some of these fungi were dedicated to bioremediation of soils, synthesis of natural products, and synthesis of drug metabolites of different substrates and showed that fungi may catalyze typical mammalian phase I as well as some phase II metabolic reactions. [22][23][24][25][26][27][28] These types of reactions might also occur in cadavers colonized by such fungi. Failure to recognize such changes and their potential relevance in a particular case could lead to false interpretation of drug concentrations and parent drug to metabolite ratios in post-mortem material.…”

“…As demonstrated in Part I of this communication and by other authors, the most common fungi colonizing cadavers belong to the genera Candida , Aspergillus , Penicillium , Mucor , Geotrichum, Fusarium, and Trichosporon. In vitro studies with some of these fungi were dedicated to bioremediation of soils, synthesis of natural products, and synthesis of drug metabolites of different substrates and showed that fungi may catalyze typical mammalian phase I as well as some phase II metabolic reactions . These types of reactions might also occur in cadavers colonized by such fungi.…”

Biotransformation of Steroids Using Different Microorganisms

“…One of the steroids used in the treatment of breast cancer is exemestane (211), an inhibitor of steroidal aromatase. From the transformation of 211 using Macrophomina phaseolina, 16β,17β-dihydroxy-6-methylene-androsta-1,4-diene-3-one (212), 17β-hydroxy-6-methylene-androsta-1,4-diene-3,16-dione (213), and 17β-hydroxy-6-methylene-androsta-1,4-diene-3-one (214) were obtained, while by using Fusarium lini, the only product obtained was 11α-hydroxy-6-methyleneandrosta-1,4-diene-3,17-dione (215) (Figure 28 products in the C-7 (7α-hydroxymethyltestosterone, 223, 35%) and C-15 (15α-hydroxymethyltestosterone, 224, 21%) positions, plus a dihydroxylated product (12,15α-dihydroxymethyltestosterone, 225, 22%) [100]. Recently, three additional products were identified: 11α-hydroxy-17α-methyltestosterone (226), 6β-hydroxy-17α-methyltestosterone (227), and 6β,11α-dihydroxy-17α-methyltestosterone (228).…”

Production of biotechnological useful metabolites by Mucor racemosus in Czapek-Dox liquid media supplemented with synthetic detergent

“…Recent studies have shown that M. racemosus may be employed to biotransform some steroid compounds, such as progesterone [15], methyltestosterone [16] and 20(s)-protopanaxatriol [17] to intermediates with anti-cancer activities. Likewise, the fungus grown on synthetic and organic substrates may be used for the production of various enzymes such as invertase, alkaline phosphatase, protease and lipase, which are of biotechnological and bioremediation interest [18].…”