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Page 24 of 50 Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02

Figure 39. Microbial transformation of mesterolone (194) with Cephalosporium aphidicola, Rhizopus stolonifer, and Fusarium lini.

Figure 40. Microbial transformation of mesterolone (194) with Cunninghamella blakesleeana, and Macrophomina phaseolina.

metenolone acetate (220) was carried out under ambient reaction conditions using Rhizopus stolonifer,
Fusarium lini, Cunninghamella elegans, and Aspergillus alliaceous. This afforded fourteen transformed
products, 6α-hydroxy-1-methyl-3-oxo-5α-androst-1-en-17-yl acetate (221) (1.1%), 6α, 17β-dihydroxy-1-
methyl-3-oxo-5α-androst-1-en (222) (1.0%), 7β-hydroxy-1-methyl-3-oxo-5α-androst-1-en-17-yl acetate (
223) (0.50%), 15β, 20-dihydroxy-1-methyl-3-oxo-5α-androst-1-en-17-yl acetate (224) (2.6%), 15β-hydroxy-
1-methyl-3-oxo-5α-androst-1-en-17-yl acetate (225) (1.0%), 17β-hydroxy-1-methyl-3-oxoandrosta-1,4-dien
[65]
(226) (0.40%) [Figure 42], 17β-hydroxy-1-methyl-3-oxo-5α-androst-1-en (227) (7.1%) , 17β-hydroxy-1-
methyl-3-oxo-5β-androst-1-en (228) (0.84%), 1-methyl-5β-androst-1-en-3,17-dione (229) (0.30%), 12β, 17β-
dihydroxy-1-methyl-3-oxoandrosta-1, 4-dien (230) (0.70%), 1-methyl-androsta-1, 4-dien-3, 17-dione (231)
(24.4%), 17β-hydroxy-1α-methyl-5α-androstan-3-one (232) (0.45%), 17β, 15α-dihydroxy-1α-methyl-5α-
androstan-3-one (233) (1.0%), and 7β, 15β, 17β-trihydroxy-1-methyl-3-oxo-5α-androst-1-en (234) (0.54%).
Among them, compounds 221-225, 230, and 234 were identified as new [Figure 43], Compounds 220
[65]
(62.5% ± 4.4%), 221 (73.4% ± 0.6 %), 224 (81.0% ± 2.5 %), 227 (69.7% ± 1.4%), 229 (73.2% ± 0.3%), 232 (60.1%
±