The covalent interactions between proanthocyanidins (PAs) and pectin during thermal processing was investigated. An acid-butanol assay clearly showed that PAs were covalently bound to pectin. Computational studies indicated that a nucleophilic substitution reaction occurred between the carbocation generated by the PAs and carboxyl or hydroxyl groups on the pectin, leading to the formation of PAs-pectin adducts. Thermal processing and PAs significantly affected the physicochemical, functional, and biological properties of pectin. Thermal processing reduced the molecular weight and increased the gelling properties of pectin, whereas PAs increased both the molecular weight and the gelling properties. Finally, we found that the covalent attachment of PAs to pectin greatly enhanced its antioxidant, prebiotic, and α-glucosidase inhibitory activity. Overall, our results suggest that the thermal processing of fruits has the potential to induce a covalent interaction between PAs and pectin, which would impact the physicochemical characteristics and functional properties of pectin.
Keywords: covalent interaction; density functional theory; functional properties; pectin; physicochemical characteristics; proanthocyanidins.