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The microbial hydroxylation of levonorgestrel.

Muhammad Iqbal Choudhary1, Muhammad Atif, Sarfraz A Nawaz

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Microbial transformation of levonorgestrel yielded novel hydroxylated metabolites. Two compounds, 2 and 5, demonstrated significant inhibitory activity against acetylcholinesterase and butyrylcholinesterase.

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Area of Science:

  • Microbiology
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Levonorgestrel is a synthetic progestogen used in hormonal contraceptives and hormone replacement therapy.
  • Microbial transformations offer a sustainable route for synthesizing novel drug derivatives with potentially altered pharmacological profiles.
  • Understanding the biotransformation of levonorgestrel is crucial for discovering new therapeutic agents.

Purpose of the Study:

  • To investigate the microbial transformation of levonorgestrel using Cunningham elegans and other fungi.
  • To identify and structurally characterize the resulting metabolites.
  • To evaluate the inhibitory potential of these metabolites against key cholinesterase enzymes.

Main Methods:

  • Microbial fermentation of levonorgestrel with Cunningham elegans, Rhizopus stolonifer, Fusarium lini, and Curvularia lunata.
  • Structural elucidation of metabolites using spectroscopic techniques.
  • In vitro enzyme inhibition assays for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).

Main Results:

  • Five hydroxylated metabolites of levonorgestrel were identified, including a new compound (metabolite 6).
  • Compounds 2 and 5 showed potent inhibitory activity against acetylcholinesterase (AChE) with IC50 values of 79.2 and 24.5 µM, respectively.
  • Metabolites 2 and 5 also exhibited inhibitory activity against butyrylcholinesterase (BChE), with IC50 values ranging from 9.4 to 309.8 µM.

Conclusions:

  • Microbial biotransformation is an effective strategy for generating novel levonorgestrel derivatives.
  • The identified metabolites, particularly compounds 2 and 5, possess significant cholinesterase inhibitory properties.
  • These findings suggest potential therapeutic applications for levonorgestrel metabolites in conditions involving cholinergic dysfunction.