Enzymatic Acylation of Proanthocyanidin Dimers from Acacia Mearnsii Bark: Effect on Lipophilic and Antioxidant Properties

Proanthocyanin (PA) dimers isolated from Acacia mearnsii bark were enzymatically acylated with palmitic acid as the acyl donor by immobilized Candida antarctica lipase on acrylic resin (Novozym 435). The acylation reaction conditions were optimized by comparing the amount of enzyme, the temperature, the reaction solvents, initial water content, substrate molar ratios and reaction time. The highest acylation conversion of 96.53% was achieved under the follow conditions: PA dimers/palmitic acid at a molar ratio of 1꞉10 in tert-amyl alcohol; initial water content of 5% at 60 °C for 12 h with 30 g/L enzyme dosage. Introducing palmitic acid into PA dimers significantly improved both the lipophilicity and antioxidant properties. The 1-octanol/water partition coefficient of the PA dimers and their derivatives showed that the lipophilicity of the derivatives were 2.4 times higher than that of the PA dimers. The derivatives exhibited strong antioxidant scavenging capacities, approximately 1.6 times greater than the original dimers. This work is of great significance to expand the application of natural PA dimers in cosmetic and food industries and also lay a foundation for the high value-added utilization of A. mearnsii.