Lignan constituents with α-amylase and α-glucosidase inhibitory activities from the fruits of Viburnum urceolatum

Abstract

Eleven previously undescribed lignan constituents, including five 8-O-4′ type neolignans, viburnurcosides A–E (1–5), three benzofuran type neolignans, viburnurcosides F–H (6–8), and three tetrahydrofuran type lignans, viburnurcosides I–K (9–11), were isolated from the fruits of Viburnum urceolatum. The structures of all isolates were elucidated by an extensive analysis of the NMR and HRESIMS data. The absolute configurations of these compounds were determined by quantum-chemical electronic circular dichroism calculation and comparison. The sugar units of viburnurcosides A–K were identified by acid hydrolysis and HPLC analysis of the chiral derivatives of monosaccharides. The in vitro enzyme inhibition assay exhibited that viburnurcoside J (10) had the most potent inhibitory activity against α-amylase and α-glucosidase with the IC50 values of 19.75 and 9.14 μM, respectively, which were stronger than those of the positive control acarbose (37.31 and 26.75 μM, respectively). The potential binding modes of viburnurcoside J (10) with α-amylase and α-glucosidase were also analyzed by molecular modeling.