Computational design of a chitosan derivative for improving the color stability of anthocyanins: Theoretical calculation and experimental verification

The objective of this study was to design a chitosan (CS) derivative with good protective effect on the color stability of anthocyanins (ACNs) under accelerated storage. The binding affinities and interactions of 12 organic acids with cyanidin-3-O-glucoside (C3G) were evaluated using quantum mechanics method. Sinapic acid (SinA) showing the strongest interaction with C3G was selected for the synthesis of SinA-grafted-CS (SinA-g-CS), which was further characterized by FTIR and 1H NMR. Under accelerated storage conditions (40 °C), SinA-g-CS significantly improved the color stability of black rice anthocyanins (BRA) in the presence of l-ascorbic acid (pH 3.0), and showed a better protective effect than that of CS. Moreover, molecular dynamics simulation analysis showed SinA-g-CS formed more hydrogen bonds with C3G than CS. Our study demonstrated that SinA-g-CS designed by computational methods can effectively protect ACNs from degradation, and has the potential to be used in ACN-rich beverages as a replacement for CS.