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Microbial transformation of prednisone.
M Iqbal Choudhary1, Zafar Ali Siddiqui, S Ghulam Musharraf
1H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi-75270, Pakistan. hej@cyber.net.pk
Natural Product Research
|June 9, 2005
Summary
Microbial transformation of prednisone yielded new metabolites. One new compound, 17alpha,20S,21-trihydroxy-5alpha-pregn-1-ene-3,11-dione, inhibited lipoxygenase activity.
Area of Science:
- Microbiology
- Medicinal Chemistry
- Enzymology
Background:
- Prednisone is a widely used corticosteroid.
- Microbial transformations are crucial for drug modification and metabolite identification.
- Understanding drug metabolism can lead to the development of new therapeutic agents.
Purpose of the Study:
- To investigate the microbial transformation of prednisone using various fungal species.
- To identify and characterize the resulting metabolites.
- To evaluate the biological activity of the novel metabolites.
Main Methods:
- Fermentation of prednisone using Cunninghamella elegans, Fusarium lini, Rhizopus stolonifer, and Curvularia lunata.
- Structure elucidation of metabolites using spectroscopic techniques (e.g., NMR, Mass Spectrometry).
- In vitro assay to determine inhibitory activity against lipoxygenase enzyme.
Main Results:
- Cunninghamella elegans produced two metabolites: 17alpha,21-dihydroxy-5alpha-pregn-1-ene-3,11,20-trione and a new compound, 17alpha,20S,21-trihydroxy-5alpha-pregn-1-ene-3,11-dione.
- Fusarium lini, Rhizopus stolonifer, and Curvularia lunata yielded 1,4-pregnadiene-17alpha,20S,21-triol-3,11-dione.
- The newly identified metabolite demonstrated inhibitory activity against lipoxygenase.
Conclusions:
- Microbial biotransformation is an effective method for generating prednisone derivatives.
- A novel prednisone metabolite with potential anti-inflammatory properties was discovered.
- Further research into this metabolite could lead to new therapeutic applications.