An efficient biotransformation of progesterone into 11α-hydroxyprogesterone by Rhizopus microsporus var. oligosporus

Z Naturforsch C J Biosci. 2018 Dec 19;74(1-2):9-15. doi: 10.1515/znc-2018-0092.

Abstract

Rhizopus microsporus var. oligosporus is a fungus that belongs to the Mucoraceae family that is used for the preparation of some soy-fermented foods. Microbial biotransformation of progesterone by R. microsporus var. oligosporus afforded some monohydroxylated and dihydroxylated metabolites. The main product was purified using chromatographic methods and identified as 11α-hydroxyprogesterone on the basis of its spectroscopic features. Time course studies by high-performance thin-layer chromatography demonstrated that this fungi efficiently hydroxylated progesterone at the 11α-position for 3 days with a yield of 76.48%, but beyond this time, the microorganism transformed 11α-hydroxyprogesterone into dihydroxylated metabolites. 11α-Hydroxyprogesterone is widely used as a precursor in the synthesis of hydrocortisone and other steroidal anti-inflammatory agents.

Keywords: 11α-hydroxyprogesterone; Rhizopus microsporus var. oligosporus; biotransformation; progesterone.

MeSH terms

  • Biomass
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Hydroxylation
  • Hydroxyprogesterones / chemistry
  • Hydroxyprogesterones / metabolism*
  • Magnetic Resonance Spectroscopy
  • Progesterone / chemistry
  • Progesterone / metabolism*
  • Rhizopus / growth & development
  • Rhizopus / metabolism*

Substances

  • Hydroxyprogesterones
  • Progesterone