Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

A series of 3-styrylchromone derivatives (4-20) were synthesized and the structure-activity relationships for alpha-glucosidase inhibition and antioxidant activities were analyzed. Among the synthesized compounds, compounds 15 and 20, which contain a catechol moiety, showed both potent 1,1-dipheny1-2-picrylhydrazyl (DPPH) free radical scavenging activity (15: EC50=17 mu m; 20: EC50=23 mu m) and alpha-glucosidase inhibitory activity (15: IC50=16 mu m; 20: IC50=10 mu m). Our data suggest that 3-styrylchromone derivatives are novel alpha-glucosidase inhibitors that have the potential to counteract diet-induced hyperglycemia in diabetes.