Biotransformation of anabolic drug Dianabol with Rizhopus oryzae

Abstract

Microbial biotransformation technique is an excellent approach for the synthesis of stereo-, enantio-, chemo-, and regio-selective/specific analogues of existing steroidal and non-steroidal drugs by using bacteria, fungi, algae, actinomycetes, yeast, and plants and animals cell cultures. This technique is effectively used to synthesize compounds whose structures resemble to the substrates (parent drugs) without using protecting/deprotecting steps. In the current study, an anabolic-androgenic steroid (AAS) based drug, methandienone (dianabol) (1) was incubated with the filamentous fungi Rhizopus oryzae ATCC 11145 for twelve days under ambient reaction conditions (at room temperature and neutral pH) by using aqueous media. Therefore, the present study has successfully helped to produce the structural analogues of inert steroidal anabolic drug dianabol (1) without using expensive and toxic chemicals. This yielded five known structural analogues of dianabol (1), i.e., 17β,11β-dihydroxy,17α-methyl-androsta-1,4-diene-3-one (2), 17β-hydroxy,17α-methyl-androsta-1,4-diene-3,11-dione (3), 17β,6β-dihydroxy,17α-methyl-androsta-1,4-diene-3-one (4), 17β,6β-dihydroxy,17α-methyl-androsta-4-ene-3-one (5), and 17β-hydroxy,17α-methyl-androsta-4,6-diene-3-one (6). Structures of transformed products 2-6 were determined through 1H-NMR, and FAB-MS spectroscopic techniques.