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Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02 Page 43 of 50

Figure 74. Biotransformation of 20-hydroxymethylpregna-1,4-dien-3-one (395) with Cunninghamella elegans.

Figure 75. Biotransformation of 6-dehydroprogesterone (395) with Macrophomina phaseolina.

Hydroxylation in derivatives, 13-hydroxyisolongi-folen-4-one (37) (IC = 9.64 ± 0.0008 μM) and 9-
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hydroxyisolongifolen-4-one (40) (IC = 6.68 ± 0.0096 μM), has increased their activities against tyrosinase,
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as compared to substrate, (+)-isolongifolen-4-one (35) (IC = 51.91 ± 0.0245 μM). Similarly, hydroxylation
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in derivatives, 17α-ethynyl-11α, 17β-dihydroxyandrost-4-en-3-one (278) (IC = 5.95 ± 0.00078 μM), 17α-
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ethyl-11α, 17β-dihydroxyandrost-4-en-3-one (284) (IC = 3.46 ± 0.01046 μM), and 17α-ethyl-6α, 17β-
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dihydroxy-5α-androstan-3-one (285) (IC = 1.72 ± 0.00089 μM) also increased their tyrosinase inhibitory
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activities, as compared to substrate, ethisterone (277) (IC = 2.61 ± 0.037328 μM).
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Structural changes in metabolites, 4β-methoxycaryophyllene-5α, 14-diol (46) (IC = 3.09 ± 2.61 μg/mL), 4β-
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methoxycaryophyllene-5α, 15-diol (47) (IC = 0.72 ± 0.17 μg/mL), and caryophyllene-5α,15-diol (48) (IC =
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1.35 ± 0.43 μg/mL), have significantly increased their anti-malarial activity in vitro, in comparison to the