Fungal transformation of norandrostenedione with Cunninghamella blakesleeana and anti-bacterial activity of the transformed products

Steroids. 2020 Oct:162:108679. doi: 10.1016/j.steroids.2020.108679. Epub 2020 Jun 20.

Abstract

Although the discovery of antibiotics has decreased the spread and severity of infectious diseases, their uncontrolled use has lead to the emergence of bacterial resistance to existing chemotherapeutic agents. Bacterial disease thus remains a challenge for health authorities in worldwide and especially in sub-Saharan Africa. Despite their efficacy, the miss-use of medicinal plants for the treatment of infectious diseases couple to the farming and hunting activities has contribute enormously to the destruction of many medicinal plant species. In search of an alternative for new and effective agents against bacterial infection, norandrostenedion (19-nor-4-androsten-3,17-dione) (1), was biotransformed by Cunninghamella blakesleeana ATCC 8688A and yielded a new metabolite, 6α,10 β -dihydroxy-19-nor-4-androsten-3-one (2), together with three known compounds, 10 β -hydroxy-19-nor-4-androsten-3,17-dione (3), 6 β,10 β,17 β -trihydroxy-19-nor-4-androsten-3-one (4) and 10 β,17 β -dihydroxy-19-nor-4-androsten-3-one (5). Their structures were elucidated on the basis ofspectroscopic techniques: NMR analysis (1D and 2D) and HRIE-MS and by comparison with previously reported data. In addition, the agar diffusion method was used to evaluate the diameter of the inhibition zone and INT colorimetric assay for MIC values. All metabolites obtained showed a potent and varied activity against tested bacteria. These results support the uses of biotransformation to develop new antimicrobial compounds for clinical application.

Keywords: Antibacterial activity; Biotransformation; Cunninghamella blakesleeana; Norandrostenedione.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstenedione / analogs & derivatives*
  • Androstenedione / chemistry
  • Androstenedione / metabolism
  • Androstenedione / pharmacology
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism*
  • Anti-Bacterial Agents / pharmacology*
  • Biotransformation
  • Cunninghamella / metabolism*
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Androstenedione
  • 19-norandrostenedione

Supplementary concepts

  • Cunninghamella blakesleeana