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Page 18 of 50 Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02

Figure 30. Biotransformation of dihydrotestosterone (134) with Fusarium oxysporum.

Supplementary Figure 6].

Biotransformation of androsterone (137)
Trichothecium roseum-catalyzed biotransformation of another steroidal hormone androsterone (137)
[48]
afforded 3α, 17β-dihydroxyandrostane (138) (21.5%) [Figure 31] [Supplementary Figure 6].
Biotransformation of trans-androsterone (139)
Transformed product 3β, 7β-dihydroxy-5α-androstan17-one (140) (5.1%) was obtained from the
fermentation of steroidal hormone trans-androsterone (139) with the Rhizopus stolonifer fungal culture,
while two derivatives 6β-hydroxy-5α-androstan-3, 17-dione (141) (0.5%) and 3β, 6β-dihydroxy-5α-
androstan-17-one (142) (0.5%) were isolated from the transformation of substrate 139 with the fungal
culture of Fusarium lini [Figure 32].
[49]

Biotransformation of dehydroepiandrosterone (143)
Fermentation of dehydroepiandrosterone (DHEA) (143) with the fungal cell culture of Cephalosporium
aphidicola resulted in two derivatives, 3β-hydroxy androst-4-en-17-one (144) (14%), and 3β, 4β-
dihydroxyandrost-5-en-17-one (145) (17.3%) [Figure 33]. Similarly, biotransformation of DHEA (143)
[48]
with another fungal cell culture Rhizopus stolonifer yielded seven metabolites, 3β, 17β-dihydroxyandrost-5-
ene (146) (20%), 3β, 17β-dihydroxyandrost-4-ene (147) (12%), 17β-hydroxyandrost-4-ene-3-one (148)
(34%), 3β, 11β-dihydroxyandrost-4-ene-17-one (149) (15%), 3β, 7α-dihydroandrost-5-ene-17-one (150)
(12%), 3β, 7α, 17β-trihydroxyandrost-5-ene (151) (20%), and 11β-hydroxyandrost-4, 6-diene-3, 17-dione (
152) (15%) [Figure 33]. The metabolites, 5β-androstane-3, 17-dione (153), 5α-androstane-3, 17-dione (
[50]
154), androst-4-ene-3, 17-dione (155), and 17β-hydroxyandrost-4-en-3-one (156) were isolated through the
biotransformation of 143 with plant cell culture Codiaeum variegatum [Figure 34].
[51]

In addition, M. phaseolina-catalyzed transformation of DHEA (143) resulted in the synthesis of eight
metabolites 146, 150, 154-156, 17β-hydroxy-androst-4,6-diene-3-one (157), 3β-hydroxy-androst-4-en-6, 17-
dione (158), and 3β, 7β, 17β-trihydroxy-androst-4-en (159) [Figure 34]. Compounds 143 (IC = 77.9 ±
[52]
50
1.95 μM), 150 (IC = 373.5 ± 9.57 μM), 152 (IC = 430 ± 7.13 μM), 154 (IC = 221.6 ± 12.5 μM), and 155 (IC
50
50
50
= 191.4 ± 1.17 μM) showed significant activity against β-glucuronidase enzyme, while metabolites 146,
50
150, 155, and 157 were found to be inactive. β-Glucuronidase is an enzyme that catalyzes the hydrolysis of
glucuronides, and generates free toxins. As a result, endogenous exposure of the organs to carcinogens
increases. Its inhibition, therefore, has therapeutic significance against diseases such as colorectal
carcinoma, GI tract infections, etc.
Biotransformation of boldione (160)
Biotransformation of the steroidal anabolic compound boldione (160) with the fungus Cephalosporium
aphidicola afforded six metabolites, androst-4-ene-3, 17-dione (161) (2.0%), 17β-hydroxyandrosta-1, 4-