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Page 20 of 50 Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02

Figure 34. Biotransformation of DHEA (143) with Cephalosporium aphidicola, Rhizopus stolonifer, and Codiaeum variegatum. DHEA:
dehydroepiandrosterone.

diene-3-one (162) (4.1%), 11α-hydroxyandrosta-1, 4-diene-3, 17-dione (163) (3.1%), 11α-hydroxyandrost-4-
ene-3, 17-dione (164) (2.5%), 11α, 17β-dihydroxyandrost-4-ene-3-one (165) (5.3%), and 11α, 17β-
dihydroxyandrosta-1, 4-diene-3-one (166) (2.5%) [Figure 35]. Metabolites 161–166 were also obtained via
[53]
the fermentation of 160 with Fusarium lini .

Biotransformation of adrenosterone (167)
Microbial transformation of adrenosterone (167) with Cephalosporium aphidicola yielded three metabolites,
androsta-1, 4-diene-3, 11, 17-trione (168) (11.2%), 17β-hydroxyandrost-4-ene-3, 11-dione (169) (8.1%), and
[54]
17β-hydroxyandrosta-1, 4-diene-3, 11-dione (170) (36.8%) [Figure 36]. In addition, three new
compounds, 9α-hydroxy-androsta-1-ene-3, 11, 17-trione (171) (3.3%), 9α, 17β-dihydroxy-androsta-1-ene-3,
11-dione (172) (12.4%), and 6β, 17β-dihydroxy-androsta-1-ene-3, 11-dione (173) (13.7%), along with the
known compound 6β-hydroxy-androsta-1-ene-3, 11, 17-trione (174) (4.2%) were also synthesized via the
[55]
biotransformation of 167 with Cunninghamella elegans [Figure 36].
Biotransformation of nandrolone (175)
Rhizopus stolonifer-assisted transformation of nandrolone (175) yielded the new compound 6α, 17β-
dihydroxy-19-norandrost-1, 4-dien-3-one (176) (20%), along with the known compound, 19-norandrost-4-
[56]
en-3, 17-dione (177) (34%) [Figure 37].

Three new derivatives, 10β, 12β, 17β-trihydroxy-19-nor-4-androsten-3-one (178) (0.2%), 10β, 16α, 17β-
trihydroxy-19-nor-4-androsten-3-one (179) (1.5%), and 6β, 10β, 17β-trihydroxy-19-nor-4-androsten-3-one (
180) (0.5%), along with four known metabolites, 10β, 17β-dihydroxy-19-nor-4-androsten-3-one (181)
(0.25%), 10β-hydroxy-19-nor-4-androsten-3, 17-dione (182) (0.91%), and 16β, 17β-dihydroxy-19-nor-4-
[57]
androsten-3-one (183) (0.83%) [Figure 37]. Compounds 175 (IC = 32.0 ± 0.5 μM), 178 (IC ≥ 100 μM),
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179 (IC = 77.39 ± 5.52 μM), 180 (IC = 70.90 ± 1.16 μM), 181 (IC = 54.94 ± 1.01 μM), 182 (IC = 80.23 ±
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3.39 μM), and 183 (IC = 61.12 ± 1.39 μM) exhibited significant anti-leishmanial activity in vitro against
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Leishmania major. Leishmaniasis is a parasitic neglected tropical disease (NTD) affecting millions of people
in over 80 countries in the global south. It causes self-healing lesions to be single and large skin ulcers.