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Microbial transformation of pyrethrosin.

A M Galal¹

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Mississippi 38677, USA. amgalalv@yahoo.com

Journal of Natural Products

|August 25, 2001

Summary

Microbial transformation of pyrethrosin yielded a new eudesmanolide and known compounds. These natural products show promising cytotoxic, antifungal, and antiprotozoal activities.

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Area of Science:

Natural Product Chemistry
Microbiology
Medicinal Chemistry

Background:

Germacranolides are a class of sesquiterpenoids with diverse biological activities.
Microbial transformations are valuable tools for generating novel chemical entities from natural products.

Purpose of the Study:

To investigate the microbial transformation of pyrethrosin using Rhizopus nigricans.
To isolate and characterize new metabolites with potential therapeutic applications.

Main Methods:

Microbial transformation of pyrethrosin (1) using Rhizopus nigricans NRRL 1477.
Structure elucidation of isolated metabolites using 1D and 2D Nuclear Magnetic Resonance (NMR) analyses.
Evaluation of biological activities including cytotoxicity, antifungal, and antiprotozoal assays.

Main Results:

Isolation of a new eudesmanolide-type metabolite, 6 alpha-acetoxy-1 beta,4 alpha-dihydroxy-5,7 alpha H,8 beta H-eudesm-11 beta,13-dihydro-8,12-olide (5).
Co-isolation of previously reported eudesmanolides (2, 3, 4, and 6).
Demonstration of cytotoxic, antifungal, and antiprotozoal activities for the isolated metabolites.

Conclusions:

Rhizopus nigricans NRRL 1477 effectively transforms pyrethrosin into novel and known eudesmanolides.
The isolated eudesmanolides possess significant biological activities, highlighting their potential as leads for drug discovery.
NMR spectroscopy is crucial for the structural determination of complex natural products.

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