Abstract
Synthesis of structured phosphatidylcholine (PC) enriched with myristic acid (MA) was conducted by acidolysis and interesterification reactions using immobilized lipases as catalysts and two acyl donors: trimyristin (TMA) isolated from ground nutmeg, and myristic acid obtained by saponification of TMA. Screening experiments indicated that the most effective biocatalyst for interesterification was Rhizomucor miehei lipase (RML), whereas for acidolysis, the most active were Thermomyces lanuginosus lipase (TLL) and RML. The effect of the molar ratio of substrates (egg-yolk PC/acyl donor), enzyme loading, and different solvent on the incorporation of MA into PC and on PC recovery was studied. The maximal incorporation of MA (44 wt%) was achieved after 48 h of RML-catalyzed interesterification in hexane using substrates molar ratio (PC/trimyristin) 1/5 and 30% enzyme load. Comparable results were obtained in toluene with 1/3 substrates molar ratio. Interesterification of PC with trimyristin resulted in significantly higher MA incorporation than acidolysis with myristic acid, particularly in the reactions catalyzed by RML.
Highlights
Myristic acid (MA) is a 14-carbon lipid molecule belonging to long-chain saturated fatty acids.It usually accounts for small amounts of total fatty acids (FA) in animal tissues, but is more abundant in milk fat (7–12 wt% of total FA) [1]
Interesterification of PC with trimyristin resulted in significantly higher MA incorporation than acidolysis with myristic acid, in the reactions catalyzed by Rhizomucor miehei lipase (RML)
In the presented work, continuing our studies on the enzymatic production of PLs using acyl donors of natural origin, we report on the lipase catalyzed-production of MA-enriched PC using two acyl donors: trimyristin (TMA) prepared from nutmeg, and MA obtained from trimyristin by Catalysts 2018, 8, x FOR PEER REVIEW
Summary
Myristic acid (MA) is a 14-carbon lipid molecule belonging to long-chain saturated fatty acids. We reported on a pioneer method for the production of structured phosphatidylcholine (SPC) using plant oils as the source of natural acyl donors in the form of triacylglycerols Using this methodology, phospholipids were enriched with unsaturated fatty acids from the n-3 or n-6 family in the process of interesterification with corresponding oil, that is, linseed, safflower, sunflower, borage, and primrose evening oil [27]. In the presented work, continuing our studies on the enzymatic production of PLs using acyl donors of natural origin, we report on the lipase catalyzed-production of MA-enriched PC using two acyl donors: trimyristin (TMA) prepared from nutmeg, and MA obtained from trimyristin by Catalysts 2018, 8, x FOR PEER REVIEW saponification Using these acyl donors allowed us to compare two reaction systems: interesterification obtained from trimyristin by saponification.
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