Abstract
Lipase-catalyzed acidolysis reactions of egg-yolk phosphatidylcholine (PC) with anisic (ANISA) and veratric (VERA) acids were investigated to develop a biotechnological method for the production of corresponding biologically active O-methylated phenophospholipids. Screening experiments with four commercially available immobilized lipases indicated that the most effective biocatalyst for the incorporation of ANISA into phospholipids was Novozym 435. None of the tested enzymes were able to catalyze the synthesis of PC structured with VERA. The effects of different solvents, substrate molar ratios, temperature, enzyme loading, and time of the reaction on the process of incorporation of ANISA into the phospholipids were evaluated in the next step of the study. The mixture of toluene/chloroform in the ratio 9:1 (v/v) significantly increased the incorporation of ANISA into PC. The acidolysis reaction was carried out using the selected binary solvent system, 1/15 substrate molar ratio PC/ANISA, 30% (w/w) enzyme load, and temperature of 50 °C afforded after 72 h anisoylated lysophosphatidylcholine (ANISA-LPC) and anisoylated phosphatidylcholine (ANISA-PC) in isolated yields of 28.5% and 2.5% (w/w), respectively. This is the first study reporting the production of ANISA-LPC and ANISA-PC via a one-step enzymatic method, which is an environmentally friendly alternative to the chemical synthesis of these biologically active compounds.
Highlights
Phenolic acids are a class of plant secondary metabolites that are of particular interest because of their well-documented pro-health and nutritional properties
We focused our attention on a one-step acidolysis method in which hydrolysis and esterification reactions occur simultaneously, and fatty acids from the sn-1 position of the PC substrate are gradually exchanged for added free acids until equilibrium is reached
We describe the enzymatic synthesis approach for the preparation of anisoyl-structured phospholipids via a one-step acidolysis of anisic acid and egg-yolk phosphatidylcholine
Summary
Phenolic acids are a class of plant secondary metabolites that are of particular interest because of their well-documented pro-health and nutritional properties. In this group, methoxy derivatives of benzoic acid are considered as important food constituents with potential preventive effects on several chronic diseases. P-Anisic acid (4-methoxybenzoic acid; ANISA), a constituent of Chinese star anise Its activity was evaluated as comparable to the activity of commercially used silymarin [2]. Veratric acid (3,4-dimethoxybenzoic acid; VERA), occurring in vegetables, fruits, and medicinal mushrooms, possesses biologically valuable properties. It has been evaluated that its oral administration at Catalysts 2020, 10, 538; doi:10.3390/catal10050538 www.mdpi.com/journal/catalysts
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