2. Academic Validation
  3. Microbial transformation of oral contraceptive ethisterone by Aspergillus niger and Cunninghamella blakesleeana

Microbial transformation of oral contraceptive ethisterone by Aspergillus niger and Cunninghamella blakesleeana

  • Steroids. 2020 Feb;154:108467. doi: 10.1016/j.steroids.2019.108467.
Ambreen Aziz 1,  Saira Bano 1,  Atia-Tul-Wahab 2,  M Iqbal Choudhary 3
Affiliations

Affiliations

  • 1 H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
  • 2 Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. Electronic address: atia.tulwahab@iccs.edu.
  • 3 H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Department of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, Almaty 050040, Kazakhstan. Electronic address: iqbal.choudhary@iccs.edu.
PMID: 31400394 DOI: 10.1016/j.steroids.2019.108467
Abstract

Ethisterone (17α-ethynyl-17β-hydroxyandrost-4-en-3-one) (1) is a synthetic steroidal estrogen. It is extensively used as an oral contraceptive. The current study involves the structural transformation of ethisterone (1) by Aspergillus niger, and Cunninghamella blakesleeana. Fermentation of 1 with C. blakesleeana afforded two new polar metabolites, 17α-ethynyl-6β,15β,17β-trihydroxyandrost-4-en-3-one, and 17α-ethynyl-7β,15β,17β-trihydroxyandrost-4-en-3-one, while transformation of ethisterone with A. niger yielded a new metabolite, 17α-ethynyl-6α,17β-dihydroxyandrost-4-en-3-one, along with a known metabolite, 17α-ethynyl-11α,17β-dihydroxyandrost-4-en-3-one. Modern spectroscopic techniques were used to characterize the structures of all transformed products.

Keywords

Aspergillus niger; Biotransformation; Cunninghamella blakesleeana; Estrogen; Ethisterone; Oral contraceptive.

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