Production of structured phosphatidylcholine with high content of DHA/EPA by immobilized phospholipase A₁-catalyzed transesterification.

Xiang Li,Bo Yang,Jia-Feng Chen,Dao-Ming Li,Yong-Hua Wang,Wei-Fei Wang

doi:10.3390/ijms150915244

Abstract

This paper presents the synthesis of structured phosphatidylcholine (PC) enriched with docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) by transesterification of DHA/EPA-rich ethyl esters with PC using immobilized phospholipsase A1 (PLA1) in solvent-free medium. Firstly, liquid PLA1 was immobilized on resin D380, and it was found that a pH of 5 and a support/PLA1 ratio (w/v) of 1:3 were the best conditions for the adsorption. Secondly, the immobilized PLA1 was used to catalyze transesterification of PC and DHA/EPA-rich ethyl esters. The maximal incorporation of DHA and EPA achieved was 30.7% for 24 h of reaction at 55 °C using a substrate mass ratio (PC/ethyl esters) of 1:6, an immobilized PLA1 loading of 15% and water dosage of 1.25%. Then the reaction mixture was analyzed by 31P nuclear magnetic resonance (NMR). The composition of reaction product included 16.5% PC, 26.3% 2-diacyl-sn-glycero-3-lysophosphatidylcholine (1-LPC), 31.4% 1-diacyl-sn-glycero-3-lysophosphatidylcholine (2-LPC), and 25.8% sn-glycerol-3-phosphatidylcholine (GPC).

Highlights

Structured phospholipids (SPL) attract attention because of their special function in food, cosmetics and pharmaceutical industries [1]
The immobilization of Phospholipase A1 (PLA1) was performed, and resin D380 was selected to be the support for the enzyme
D380 is a macroporous and weakly basic anion exchange resin and it could form ionic bonds between functional group (–NH2) and the amino acid residues in protein molecules, which is helpful to show higher enzyme activity [13]. Factors such as the ratio of support/PLA1and pH were selected to investigate their effects on the protein load and the activity of immobilized PLA1

Summary

Introduction

Structured phospholipids (SPL) attract attention because of their special function in food, cosmetics and pharmaceutical industries [1]. The constituents and concentrations of incorporated fatty acids in the SPL’s scaffold can influence their physiological, physiochemical and biochemical characteristics. Novel SPL could be created by incorporating functional fatty acids (e.g., docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA)) into natural PL. Docosahexaenoic (DHA; C22:6) and eicosapentaenoic (EPA; C20:5), which are functional n-3 polyunsaturated fatty acids (PUFA), have multiple biochemical and pharmacological effects on human health and treatment/prevention of some diseases [2,3,4]. It has been demonstrated that n-3 PUFA could be absorbed and have higher bioavailability in the body as PL than as the corresponding triglycerides or ethyl esters [5]. Cansell et al [6] have reported that DHA is less subjected to peroxidation when linked to phospholipids (PL) than to triglycerides or ethyl esters. More research on DHA/EPA-rich SPL will benefit its production

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