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The 11α-hydroxylation of medroxyprogesterone acetate by Absidia griseolla var. igachii and Acremonium chrysogenum

Saba Ghasemi1, Marjan Heidary2, Zohreh Habibi2

  • 1Department of Chemistry, Ilam Branch, Islamic Azad University, Ilam, Iran.

Steroids
|June 23, 2019
PubMed

Insights

Two fungi biotransformed medroxyprogesterone acetate (MPA) into a novel metabolite, 11α-hydroxy-medroxyprogesterone acetate. Optimal conditions for this fungal biotransformation were identified, yielding significant metabolite production.

Area of Science:

  • Microbial biotransformation of steroids
  • Synthetic chemistry and drug development
  • Biocatalysis and fermentation technology

Background:

  • Medroxyprogesterone acetate (MPA) is a synthetic progestin with various therapeutic applications.
  • Microbial transformation offers a sustainable and efficient route for steroid modification.
  • Exploring novel biotransformation pathways can lead to the discovery of new drug derivatives.

Purpose of the Study:

  • To investigate the fungal biotransformation of MPA using selected filamentous fungi.
  • To identify and characterize the major metabolite produced from MPA.
  • To optimize fermentation conditions for enhanced metabolite production.

Main Methods:

  • Biotransformation assays using Absidia griseolla var. igachii and Acremonium chrysogenum.
  • Structure elucidation of the metabolite using 1D- and 2D-NMR, EI-MS, and elemental analysis.
  • High-Performance Liquid Chromatography (HPLC) for time course studies and yield determination.
  • Optimization of fermentation parameters including temperature and substrate concentration.

Main Results:

  • MPA was successfully biotransformed into 11α-hydroxy-medroxyprogesterone acetate by both fungal strains.
  • The structure of the metabolite was confirmed through comprehensive spectroscopic analysis.
  • HPLC analysis indicated metabolite yields of 63% and 48% for A. griseolla and A. chrysogenum, respectively.
  • Optimal biotransformation conditions were determined as 25°C and 0.1% (w/v) substrate concentration.

Conclusions:

  • This study demonstrates the first reported fungal production of 11α-hydroxy-medroxyprogesterone acetate.
  • The identified fungal strains and optimized conditions provide a viable method for producing this steroid derivative.
  • This biotransformation pathway holds potential for the development of new pharmaceutical compounds.
Keywords:
11α-Hydroxy-MPAAbsidia griseollaAcremonium chrysogenumBiotransformationHydroxylationMedroxyprogesterone acetate (MPA)

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