Optimizing Nucleophilic Depolymerization of Proanthocyanidins in Grape Seeds to Dimeric Proanthocyanidin B1 or B2.

Depolymerization of polymeric proanthocyanidins (PPCs) in grape seeds into oligomeric proanthocyanidins (OPCs), especially the dimers, has important academic significance and practical value. Reaction conditions including nucleophilic reagent/PPC mass ratio, HCl concentration, reaction time, and temperature were systematically optimized by central composite design to maximize the yield of the dimeric product B2 or B1. The yield of B2 reached 3.35 mg mL-1 under the conditions of (-)-epicatechin/PPC mass ratio 2.8, HCl concentration 0.06 mol, reaction time 16 min and temperature 36 °C, and that of B1 reached 3.64 mg mL-1 under the conditions of (+)-catechin/PPC mass ratio 2.8, HCl concentration 0.07 mol, reaction time 17 min, and temperature 34 °C. Overall, this study has provided theoretical guidance and a practical approach to improvethe reaction process and economic value of proanthocyanidins in grape seed proanthocyanidin extract.