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United States Department of Agriculture

Agricultural Research Service

Title: Value-Added Products Through Biotransformation: Tetrahydrofuranyl Fatty Acids and Sn2-Monoacylglycerides

Authors
item Hou, Ching
item Irimescu, Roxana - VISITING SCIENTIST
item Iwasaki, Yugo
item Brown, Wanda

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 16, 2001
Publication Date: N/A

Technical Abstract: We have been working on biotransformation of hydroxy fatty acids and lipases. Microbial culture Clavibacter strain ALA2 transforms linoleic acid into a variety of novel unsaturated hydroxy fatty acids. The main product (30% yield) was 12,13,17-trihydroxy-9(Z)-octadecenoic acid. In our previous work, we also tentatively identified two tetrahydrofuran- (di)hydroxy fatty acids based on GC/MS data. Here, we confirm the structures of the tetrahydrofuran-(di)hydroxy fatty acids by proton and 13C nuclear magnetic resonance, as 12-hydroxy-13, 16-epoxy-9(Z)- octadecenoic acid, and 7,12-dihydroxy-13,16-epoxy-9(Z)-octadecenoic acid, respectively. The optimum conditions for production of these compounds were 70 hr of incubation at temperature 30 - 35 C and pH of 7.0 - 7.5. Bioconversion pathways for tetrahydrofuran fatty acids and 12,13,17- trihydroxy unsaturated fatty acids are different. A straightforward enzymatic method for 2-monoacylglycerol synthesis from homogenous triacylglycerols and natural fats and oils was established. The resulting 2- monoacylglycerols can be used as synthetic blocks for production of tailored triacylglycerols which have improved nutritional properties. The method consists of regiospecific ethanolysis of triacylglycerols with lipases. The process optimization (reaction temperature, substrate molar ratio, catalyst amount, etc.) and a study of lipase specificity for various substrates were performed. High reaction yields (>85%) and purity (>99%) were obtained. 2-Monoacylglycerols of polyunsaturated fatty acids like arachidonic, docosahexaenoic or eicosapentaenoic acid were obtained easily in much shorter time compared to other reported methods.

Last Modified: 8/27/2014
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