Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids.

The stereospecific structure of triacylglycerols (TAGs) affects the bioavailability of fatty acids. Lack of enantiopure reference compounds and effective enantiospecific methods have hindered the stereospecific analysis of individual TAGs. Twelve novel enantiostructured AAB-type TAGs were synthesized containing one of the three n-3 polyunsaturated fatty acid: α-linolenic acid (ALA), eicosapentaenoic acid (EPA), or docosahexaenoic acid (DHA) in sn-1 or sn-3 position.

Bioavailability of docosahexaenoic acid 22:6(n-3) from enantiopure triacylglycerols and their regioisomeric counterpart in rats.

Lack of synthetic enantiospecific triacylglycerols (TAGs) has hindered our understanding of the impact of TAG structure on the absorption and metabolic fate of fatty acids (FAs). In a five-day feeding trial with mildly (n-3) deficient rats, the bioavailability of docosahexaenoic acid [22:6(n-3), DHA] and stearic acid (18:0) from the two different enantiomers of TAG: sn-22:6(n-3)-18:0-18:0 and sn-18:0-18:0-22:6(n-3), and their regioisomeric TAG: sn-18:0-22:6(n-3)-18:0 was compared. Less secretion of fecal DHA was detected from the sn-2 position compared with the sn-1 and sn-3 positions, but no difference was found in DHA content of the fasting plasma or in the weight of the body or organs.