Samin-derived flavonolignans, a new series of antidiabetic agents having dual inhibition against α-glucosidase and free radicals

Abstract

A series of novel flavonolignans were synthesized by the reaction between a lignan named samin (1) and a range of flavonoids. This simple and rapid approach allowed direct assembly of these two bulky motifs in good yields without the formation of byproducts. Upon evaluation of antidiabetic activity of the synthesized products, epicatechinosamin (β-2g) was the most active α-glucosidase inhibitor toward maltase and sucrase. The kinetic study indicated that β-2 g inhibited the enzymes in a mixed manner of competitive and noncompetitive inhibition.

Graphical Abstract

Keywords:

• Flavonolignan
• diabetes
• glucosidase
• antioxidant
• Friedel-Crafts
• oxocarbenium

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This project was financially supported by the Thailand Research Fund (RSA5880027) and Faculty of Science, Chulalongkorn University (Sci-Super IV_61_003). W.W. is grateful to the Graduate School of Chulalongkorn University for a Postdoctoral Fellowship (Ratchadaphisek Sompot Fund). The Center of Excellent in Natural Products was subsidized by Chulalongkorn University. We thank Mr. Thammatee Potipiranun for technical assistance in the isolation and purification of natural flavonoids.