Enzymatic acylation of raspberry anthocyanin: Evaluations on its stability and oxidative stress prevention

Abstract

Raspberry anthocyanins were isolated and purified by XAD-7HP macroporous resin and silica gel column chromatography. Anthocyanins were then acylated with methyl salicylate as catalyzed by lipase under reduced pressure, and the conversion rate was 84.26%. LC-MS and NMR were used to identify the structure, and the stability, antioxidant capacity and protective ability of the acylated anthocyanins against oxidative damage were determined. The results showed that cyanindin-3-O-glucoside (C3G) was the primary anthocyanin in raspberry, and the binding site of acylation was on the glucoside C-6, and the product was cyanidin-3-(6-salicyloyl) glucoside (C3-6(S) G). After acylation, its stability in light, heat and oxidation environments could be significantly improved, and acylated ACN showed insignificant changes in antioxidant capacities to scavenge DPPH and ABTS free radicals, as well as oxygen free radical absorptive capacity (ORAC). And it could also effectively prevent the release of ROS caused by oxidative damage and alleviate oxidative stress damage.

Keywords: Cyanidin-3-O-glucoside; Enzymatic acylation; Oxidative stress damage; Raspberry; Stability.