Enzymatic synthesis of structured lipid containing arachidonic and palmitic acids

Human milk fat contains 20–25% palmitic acid, and about 70% of the fatty acid is esterified to the 2-position of triglycerides. It was also reported that arachidonic acid (AA) accelerated the growth of preterm infants. Thus, we attempted the synthesis of 1,3-arachidonoyl-2-palmitoyl-glycerol by acidolysis of tripalmitin with AA using 1,3-specific Rhizopus delemar lipase. When a mixture of 10 g tripalmitin/AA (1∶5, w/w) and 0.7 g immobilized Rhizopus lipase was incubated at 40°C for 24 h with stirring, the AA content in glycerides reached 59 mol%. The immobilized lipase could be used five times without a decrease in the extent of acidolysis. Glycerides were extracted from the reaction mixture with n-hexane, and regiospecific analysis was performed. As a result, the AA contents at the 1,3- and 2-positions were 56.9 and 3.2 mol%, respectively. It was therefore confirmed that the fatty acids at the 1,3-positions of triglyceride were exchanged for AA. High-performance liquid chromatography showed that the contents of triarachidonin, 1,3-arachidonoyl-2-palmitoyl-glycerol, and 1(3)-arachidonoyl-2,3(1)-palmitoyl-glycerol were 7.3, 75.9, and 12.4 wt%, respectively.