A new metabolite from Cunninghamella blakesleeana-mediated biotransformation of an oral contraceptive drug, levonorgestrel

Abstract

Cunninghamella blakesleeana-mediated biotransformation of an oral contraceptive drug, levonorgestrel (1), yielded a new metabolite, 13β-ethyl-17α-ethynyl-10,17β-dihydroxy-4,6-dien-3-one (2), and two known metabolites 3 (13β-ethyl-17α-ethynyl-10β,17β-dihydroxy-4-en-3-one), and 4 (13β-ethyl-17α-ethynyl-6β,17β-dihydroxy-4-en-3-one) at an ambient temperature using aqueous media. Hydroxylation and dehydrogenation of compound 1 was observed during the bio-catalytic transformation. The structure of a new metabolite 2 was determined by ¹H, ¹³C, and 2DNMR and HR-EIMS spectroscopic techniques.

Graphical Abstract

Keywords:

• Contraceptive drug
• levonorgestrel
• biotransformation
• Cunninghamella blakesleeana

Disclosure statement

No potential conflict of interest was reported by the authors.

Funding

BMK would like to acknowledge the financial support of the H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences (ICCBS), University of Karachi, Karachi 75270, Pakistan, through a scholarship, and travel support through COMSATS (Commission on Science and Technology for Sustainable Development in the South).