Immobilized Lipases—A Versatile Industrial Tool for Catalyzing Transesterification of Phytosterols Solubilized in Plant Oils to Produce Their Fatty Acid Esters

Abstract

The conjugation of phytosterols (PSs) with fatty acids results in producing phytosterol esters (PSEs) characterized by enhanced lipophilicity and improved functional properties of major interest in food and nutraceutical applications. The use of immobilized lipases to catalyze direct transesterification reactions between PSs and plant oils to form PSEs as a green alternative to conventional chemical production methods has attracted interest during the last two decades. The low solubility of PSs in common plant oil triglycerides, typically below 3% at ambient temperatures, remains the main challenge for bringing lipase-catalyzed direct transesterification reactions of PSs and oil triglycerides to commercial scales. This study focuses on the enzymatic synthesis of PSEs starting from solubilized PSs at concentrations of up to 30% wt./wt. of oil mixtures comprising fatty acid ethyl esters (FAEEs), monoglycerides (MGs), diglycerides (DGs), and triglycerides (TGs) as a homogeneous medium for the direct transesterification reaction. The results of this study show for the first time that the addition of FAEEs into the reaction medium results in an alteration of the substrate preference of the enzyme, making MGs the favorite fatty acyl group donors for PSs amongst all other fatty acyl donors present in the reaction system. The proposed new enzymatic route allows starting with high concentrations of solubilized PSs, making the direct transesterification of oil glycerides attractive for the production of PSEs at industrial scales.