Enzymatic acylation of lutein with a series of saturated fatty acid vinyl esters and the thermal stability and anti-lipid oxidation properties of the acylated derivatives.

Abstract

Lutein was enzymatically acylated with saturated fatty acid vinyl esters of different lengths of carbon chain (C6 -C14 ) under the action of Candida antarctica lipase B (Novozyme 435). The acylation reaction was optimized by considering substrate molar ratio, reaction solvent, type of enzyme, and reaction time. The highest yield (88%) was obtained using the Novozyme 435 to catalyze the acylation reaction of lutein and vinyl decanoate (lutein/vinyl decanoate molar ratio of 1/10) for 16 h in methyl tert-butyl ether. Ten lutein esters were synthesized, isolated, and purified, which were characterized by Fourier-transform infrared spectroscopy, high-resolution mass spectrometry, and nuclear magnetic resonance spectroscopy. We found that the acylation of lutein improved its antioxidant capacity in lipid system and thermal stability. Our study extended the potential application of lutein in lipophilic food, cosmetic, and pharmaceutical industries. Practical Application: Enzyme acylation of lutein improved its antioxidant capacity in lipid system and thermal stability, extended its potential application in food, cosmetic, and pharmaceutical industries. In addition, our study also provided a new perspective and cognition for the further development and utilization of lutein.