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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

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New bioactive fatty acids.

¹Microbial Genomics and Bioprocessing Research Unit, National Center for Agricultural Utilization Research, ARS, USDA. 1815 N. University Street, Peoria, IL 61604. USA. Ching.Hou@ars.usda.gov

Asia Pacific Journal of Clinical Nutrition

|May 28, 2008

Summary

Microbial bioconversion generates novel oxygenated fatty acids with significant antimicrobial and biomedical potential. These compounds, derived from common fatty acids, show promise as new therapeutic agents.

Area of Science:

Microbiology
Biochemistry
Organic Chemistry

Background:

Oxygenated fatty acids are bioactive compounds with diverse biological activities.
Microbial transformations of fatty acids yield novel structures with potential applications.
Understanding these bioconversion pathways is crucial for discovering new therapeutic agents.

Purpose of the Study:

To identify and characterize novel oxygenated fatty acids produced by microbial fermentation.
To evaluate the bioactivity of these newly synthesized compounds, particularly their antimicrobial properties.
To explore the potential of specific microbial strains for producing valuable fatty acids like arachidonic acid (AA) and dihomo-gamma-linolenic acid (DGLA).

Main Methods:

Fatty acid bioconversion using bacterial strains (e.g., Nocardia cholesterolicum, Flavobacterium DS5, Pseudomonas aeruginosa PR3, Bacillus megaterium ALA2).

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Analysis of fatty acid products using chromatographic and spectroscopic techniques.

Screening of Mortierella fungal strains for the production of AA and DGLA from glucose or glycerol.

Main Results:

Pseudomonas aeruginosa PR3 produced 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) with antibacterial activity against food-borne pathogens.
Bacillus megaterium ALA2 generated various oxygenated fatty acids, including 12,13-dihydroxy-9-octadecenoic acid (12,13-DHOA) and 12,13,17-trihydroxy-9(S)-octadecenoic acid (THOA), with anti-plant pathogenic fungal activity.
Mortierella strains efficiently produced AA and DGLA, with M. alpina being the top producer of AA.

Conclusions:

Microbial bioconversion is a viable strategy for producing novel oxygenated fatty acids with significant antimicrobial and biomedical potential.
The identified compounds, such as DOD and THOA, demonstrate promising bioactivity and warrant further investigation.
Specific fungal strains, particularly Mortierella species, are effective producers of important polyunsaturated fatty acids (PUFAs) like AA and DGLA, precursors to prostaglandins and thromboxanes.