title: Biotransformation of finasteride by Ocimum sanctum L., and tyrosinase inhibitory activity of transformed metabolites: experimental and computational insights.
abstract: 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 1.87μM. Molecular docking revealed significant molecular interactions behind the potent tyrosinase inhibitory activity of the tested compounds.
authors.affiliation: Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, Pakistan.
authors.forename: Sajid
authors.initials: S
authors.lastname: Ali
authors.affiliation: Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, Pakistan. Electronic address: akhund54@gmail.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Nisar
authors.affiliation: Department of Agricultural and Environmental Sciences, Milan State University, Milan, Italy. Electronic address: marcello.iriti@unimi.it.
authors.forename: Marcello
authors.initials: M
authors.lastname: Iriti
authors.affiliation: H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
authors.forename: Mohammad Raza
authors.initials: MR
authors.lastname: Shah
authors.affiliation: Department of Information Systems, College of Computer and Information Sciences (CCIS), King Saud University, Saudi Arabia.
authors.forename: Maqsood
authors.initials: M
authors.lastname: Mahmud
authors.affiliation: Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, Pakistan.
authors.forename: Ihsan
authors.initials: I
authors.lastname: Ali
authors.affiliation: Department of Pharmacy, University of Peshawar, Peshawar 25120, Pakistan.
authors.forename: Inamullah
authors.initials: I
authors.lastname: Khan
mesh_terms: D004791:Enzyme Inhibitors / Q000378:metabolism* / Q000494:pharmacology*; D018120:Finasteride / Q000378:metabolism* / Q000494:pharmacology*; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D031339:Ocimum / Q000378:metabolism*
chemical_list: D004791:Enzyme Inhibitors; D018120:Finasteride; D014442:Monophenol Monooxygenase
keywords: 11α-Hydroxyfinasteride; 15β-Hydroxyfinasteride; 16β-Hydroxyfinasteride; Finasteride; Ocimum sanctum L.; Tyrosinase