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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.

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Cadmium (Cd) damages the liver, kidney, bones, reproductive system, and other organs. Flavonoids, such as anthocyanins and flavonols, which are commonly found in plant foods, have shown protective effects against Cd-induced damage. The cytoprotective effects of flavonoids against Cd-induced diseases are mainly attributable to three mechanisms. First, flavonoids clear reactive oxygen species, thereby reducing lipid peroxide production and improving the activity of antioxidation enzymes. Second, flavonoids chelate Cd, thus reducing the accumulation of Cd and altering the levels of other essential metal ions in vivo. Third, flavonoids reduce DNA damage and inhibit apoptosis. In addition, flavonoids were found to inhibit inflammation and fibrosis and improve glycometabolism and the secretion of reproductive hormones. We introduce the daily dosage and absorption rate of flavonoids and then focus on their bioactive effects against Cd-induced toxicity and reveal the underlying metabolic pathway, which provides a basis for further study of the nutritional prevention of Cd-induced injury. In particular, a better understanding is needed of the structure-activity relationship of flavonoids against Cd toxicity, which has not yet been reported.