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Enzymatic synthesis of structured lipid containing arachidonic and palmitic acids
Author(s) -
Shimada Yuji,
Nagao Toshihiro,
Hamasaki Yukiko,
Akimoto Kengo,
Sugihara Akio,
Fujikawa Shigeaki,
Komemushi Sadao,
Tominaga Yoshio
Publication year - 2000
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-000-0014-8
Subject(s) - tripalmitin , glyceride , lipase , chemistry , glycerol , palmitic acid , arachidonic acid , chromatography , triglyceride , monoglyceride , fatty acid , enzyme , biochemistry , cholesterol
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.