Comparative Study on the Stability and Antioxidant Activity of Six Pyranoanthocyanins Based on Malvidin-3-glucoside

Pyranoanthocyanins are the important color and functional compounds in red wine. Six common kinds of pyranoanthocyanins were synthesized through the reaction of malvidin-3-O-glucoside (Mv-3-gluc) with acetone, pyruvic acid, p-cumaric acid, caffeic acid, ferulic acid, and sinapid acid, respectively, and their pH (1.0-11.0), SO₂ (0-250 ppm), and thermo (50-98 °C) stabilities and antioxidant activities were comparatively studied. Results showed that the six pyranoanthocyanins all exhibited higher pH and SO₂ color stability than Mv-3-gluc, especially vitisin-A with a carboxy group on the D ring. The six pyranoanthocyanins also showed much more thermostability than Mv-3-gluc, especially methylpyranomv-3-gluc. The degradation kinetics of Mv-3-gluc and its derivatives all fitted to a first-order reaction. Moreover, pinotin-A with the o-dihydroxyl group on the E ring presented the strongest antioxidant capability, as evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and ferric ion reducing power (FRAP) assays. Additionally, the increase in the number of rings is beneficial to the improvement of the DPPH radical scavenging ability of anthocyanins.