Biotransformation of Finasteride by Ocimum sanctum L., and tyrosinase inhibitory activity of transformed metabolites: Experimental and computational insights

• Finasteride was transformed by Ocimum sanctum L. culture.
• Three metabolites (16β-hydroxyfinasteride, 11α-hydroxyfinasteride and 15β-hydroxyfinasteride) were isolated.
• All compounds showed potent tyrosinase inhibitory activities.
• Docking revealed molecular insights behind inhibitory activities.

Transformation of Finasteride (I) by cell suspension cultures of Ocimum sanctum L. was investigated. Fermentation of compound (I) with O. sanctum afforded three oxidized derivatives, 16β-hydroxyfinasteride (II), 11α-hydroxyfinasteride (III) and 15β-hydroxyfinasteride (IV). Among these metabolites, compound (II) was a new metabolite. Compound (I) and its derivatives were studied for their tyrosinase inhibition assay. All test compounds exhibited significant activity compared to standard drug kojic acid, with compound IV being the most potent member with an IC50 of 1.87 μM. Molecular docking revealed significant molecular interactions behind the potent tyrosinase inhibitory activity of the tested compounds.

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