Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides.

ABSTRACT

The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12. Compound 1, 2, 7, 12 and glycyrrhizic acid (GL) were evaluated for their inhibitory activities against α-glucosidase. As a result, Compound 1, 2, 7, 12 and GL all showed significant α-glucosidase inhibitory activity and IC50 values were 0.465, 1.352, 0.759, 0.687 and 2.085 mM, respectively, and acted as non-competitive inhibitors. The activity of the compound 2, 7, 12 was lower than compound 1, but significantly higher than GL. Therefore, it was concluded that the change of structure in glycyrrhetinic acid by chemical modification had certain effect on bioactivity, and the change of carboxyl group, hydroxyl group and the type of monosaccharide introduced were the influencing factors.