Abundances of Triacylglycerol Positional Isomers and Enantiomers Comprised of a Dipalmitoylglycerol Backbone and Short- or Medium-chain Fatty Acids in Bovine Milk Fat

Toshiharu Nagai, Natsuko Watanabe, Kazuaki Yoshinaga, Hoyo Mizobe, Koichi Kojima, Ikuma Kuroda, Yuki Odanaka, Tadao Saito, Fumiaki Beppu, Naohiro Gotoh
2015 Journal of Oleo Science  
phospholipase A 2 that enabled the analysis of the fatty acid composition at the sn-1, 2, and 3 positions 3 5 . Itabashi et al. developed another stereospecific method using chiral HPLC 6, 7 . These analytical techniques have been used in many studies on the positional distributions of fatty acids in TAGs from various organisms in nature 8 10 . Bovine milk contains about 3.5 to 5 total lipid, and 98 or more of the lipid is TAG 11 . Bovine milk fat BMF is rich in palmitic acid P and oleic acid O
more » ... P and oleic acid O . Long-chain saturated fatty acids, such as myristic acid M , P, and stearic Abstract: Bovine milk fat (BMF) is composed of triacylglycerols (TAG) rich in palmitic acid (P), oleic acid (O), and short-chain or medium-chain fatty acids (SCFAs or MCFAs). The composition and binding positions of the fatty acids on the glycerol backbone determine their physical and nutritional properties. SCFAs and MCFAs are known to characteristically bind to the sn-3 position of the TAGs in BMF; however, there are very few non-destructive analyses of TAG enantiomers binding the fatty acids at this position. We previously reported a method to resolve the enantiomers of TAGs, binding both long-chain saturated fatty acid and unsaturated fatty acid at the sn-1 and 3 positions, in palm oil, fish oil, and marine mammal oil using chiral HPLC. Here, we further developed a method to resolve several TAG enantiomers containing a dipalmitoyl (PP) glycerol backbone and one SCFA (or MCFA) in BMF. We revealed that the predominant TAG structure in BMF was homochiral, such as 1,2-dipalmitoyl-3-butyroyl-sn-glycerol. This is the first quantitative determination of many TAG enantiomers, which bind to a SCFA or MCFA, in BMF was evaluated simultaneously. Furthermore, the results indicated that the amount ratios of the positional isomers and enantiomers of TAGs consisting of a dipalmitoyl (PP) glycerol backbone and SCFA (or MCFA), resembled the whole TAG structures containing the other diacylglycerol backbones consisting of P, O, myristic acid, and/or stearic acid in BMF.
doi:10.5650/jos.ess15040 pmid:26329769 fatcat:5ujzw2isqvhnznv7m3apc72q7a