Abstract
Enzymatic acidolysis of egg-yolk phosphatidylcholine (PC) with 3-methoxycinnamic acid (3-OMe-CA) was investigated to produce biologically active 3-methoxycinnamoylated phospholipids. Four commercially available lipases were screened for their ability to incorporate 3-OMe-CA into PC. The results showed that Novozym 435 is the most effective biocatalyst for this process, while during the examination of organic solvents, heptane was found propriate reaction medium. The other reaction parameters including the substrate molar ratio, enzyme load and reaction time were designed using an experimental factorial design method. According to three-level-3-factor Box-Behnken model it was shown that all of studied parameters are crucial variables for the maximization of the synthesis of structured PLs. The optimum conditions derived via response surface methodology (RSM) were: 30% of lipase of the total weight of substrates, 1:15 molar ration of PC/3-OMe-CA and reaction time 4 days. The process of acidolysis performed on the increased scale at optimized parameters afforded two products. The major product, 3-methoxycinnamoylated lysophosphatidylcholine (3-OMe-CA-LPC) was isolated in high 48% yield, while 3-methoxycinnamoylated phosphatidylcholine (3-OMe-CA-PC) was produced in trace amount only in 1.2% yield. Obtained results indicate that presented biotechnological method of synthesis of 3-methoxycinnamoylated lysophosphatidylcholine is competitive to the previously reported chemical one.
Highlights
The beneficial role of structured phospholipids (SPLs) in nutrition, health and food applications is enormous and many new literature reports in this area determine the constant increase of interest in this group of products and methods of their obtaining [1]
The currently available preparations of lipases immobilized on a hydrophobic substrate enable the catalysis of the reaction in the presence of an organic solvent which are dedicated to lipid modifications and high concentrations of substrates while maintaining a satisfactory efficiency and selectivity of the process [23]
In the case of preparation of Novozym 435 lipase B was immobilized on a microporous acrylic resin while in the case of CALB the same enzyme was immobilized on resin Immobead 150
Summary
The beneficial role of structured phospholipids (SPLs) in nutrition, health and food applications is enormous and many new literature reports in this area determine the constant increase of interest in this group of products and methods of their obtaining [1]. Compared to the chemical methods enzymatic modifications of phospholipids (PLs) are of special attention and are usually perform to alter and to improve the physiochemical or nutritional properties of PLs [1,2,3] Their main advantage is selectivity of used for phospholipid modifications biocatalysts, which make the processes of production of SPLs simpler and let to conduct them under mild conditions [4,5]. The most popular biocatalysts mostly selected due to economic aspects are immobilized lipases Their numerous advantages such as broad substrate specificity, ability to catalyze a large number of various reactions and no need to use of cofactors during reactions performed with their participation are responsible that they have become the object of special interest in food industry [6,7]. The products of this type of reactions can be applied as health-promoting substances in the form of food additives or nutraceuticals
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