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Page 28 of 50 Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02

Figure 46. Biotransformation of dianabol (245) with Macrophomina phaseolina and Cunninghamella elegans.

Figure 47. Biotransformation of methasterone (255) with Cunninghamella blakesleeana and Fusarium lini.

androstane-3, 7-dione (270) (0.51%), and 3β, 6β, 17β-trihydroxy-2α, 17α-dimethyl-5α-androstane-7-one (
[70]
271) (0.53%) were synthesized by biotransformation of drug 255 with Cunninghamella blakesleeana
[Figure 48]. Metabolites 267 and 268 showed moderate inhibition of NO production with the IC values of
50
−1
40.2 ± 3.3, and 38.1 ± 0.5 μg·mL , respectively.
BIOTRANSFORMATION OF CONTRACEPTIVE STEROIDS
Biotransformation of desogestrel (272)
Whole-cell bio-catalytic conversion of steroidal contraceptive drug desogestrel (272) by Cunninghamella
blakesleeana yielded three new metabolites, 13-ethyl-11-methylene-18, 19-dinor-17α-pregn-4-en-20-yn-6β,
15β, 17β-triol (273) (2.5%), 13-ethyl-11-methylene-18, 19-dinor-17α-pregn-4-en-20-yn-3β, 6β, 17β-triol (
274) (15.2%), and 13-ethyl-11-methylene-18, 19-dinor-17α-pregn-20-yn-3α, 5α, 6β, 17β-tetraol (275) (1.9%),
along with the known metabolite, 13-ethyl-11-methylene-18, 19-dinor-17α-pregn-4-en-20-yn-6β, 17β-
[71]
dihydroxy-3-one (276) (9.2%) [Figure 49]. Compounds 272 and 273 showed potent activity against
Staphylococcus aureus EMRSA-17, Staphylococcus aureus NCTC 13277 (MRSA-252), and Staphylococcus
aureus NCTC 13143, and clinically isolated Pakistani strain of Staphylococcus aureus in an in-vitro MABA