Biotransformation of androgenic steroid mesterolone with Cunninghamella blakesleeana and Macrophomina phaseolina.
Fermentation of mesterolone (1) with Cunninghamella blakesleeana yielded four new metabolites, 1α-methyl-1β,11β,17β-trihydroxy-5α-androstan-3-one (2), 1α-methyl-7α,11β,17β-trihydroxy-5α-androstan-3-one (3), 1α-methyl-1β,6α,17β-trihydroxy-5α-androstan-3-one (4) and 1α-methyl-1β,11α,17β-trihydroxy-5α-androstan-3-one (5), along with three known metabolites, 1α-methyl-11α,17β-dihydroxy-5α-androstan-3-one (6), 1α-methyl-6α,17β-dihydroxy-5α-androstan-3-one (7) and 1α-methyl-7α,17β-dihydroxy-5α-androstan-3-one (8). Biotransformation of 1 with Macrophomina phaseolina also yielded a new metabolite, 1α-methyl, 17β-hydroxy-5α-androstan-3,6-dione (9). The isolated metabolites were subjected to various in vitro biological assays, such as anti-cancer, inhibition of α-glucosidase, and phosphodiesterase-5 enzymes and oxidative brust. However, no significant results were observed. This is the first report of biotransformation of 1 with C. blakesleeana and M. phaseolina.
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
Malik Shoaib
MS
Ahmad
Department of Chemistry, Sarhad University of Science and Technology, Ring Road Campus, Peshawar 25120, Pakistan.
Salman
S
Zafar
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
Marium
M
Bibi
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
Saira
S
Bano
Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
Atia-Tul-Wahab
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
Atta-Ur-Rahman
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Department of Biochemistry, Faculty of Science, King Abdulaziz University, Jeddah 21412, Saudi Arabia. Electronic address: iqbal.choudhary@iccs.edu.
M
M
Iqbal Choudhary
D001203:Ascomycota / Q000737:chemistry / Q000378:metabolism*; D020093:Cunninghamella / Q000737:chemistry* / Q000378:metabolism; D008655:Mesterolone / Q000737:chemistry / Q000378:metabolism*; D008968:Molecular Conformation
D008655:Mesterolone
Andogenic compound; Biotransformation; Cunninghamella blakesleeana; Macrophomina phaseolina; Mesterolone