Coumaroyl and feruloyl flavonoid glycosides from the male flowers of Ginkgo biloba L. and their inhibitory activity against α-glucosidase

Nat Prod Res. 2022 Sep;36(17):4371-4378. doi: 10.1080/14786419.2021.1993216. Epub 2021 Dec 29.

Abstract

Four flavonoid glycosides containing coumaroyl or feruloyl groups were isolated from the male flowers of Ginkgo biloba L., and compounds 3 and 4 were identified as novel compounds. The inhibitory activities against α-glucosidase were investigated by docking studies, in vitro assays and kinetic studies. The docking results showed that all compounds mainly formed hydrogen-bond and π-π-stacking interactions with α-glucosidase. Compound 4 had the lowest binding energy and maximum number of hydrogen bonds. Subsequently, the in vitro assays showed that compound 4 exhibited the strongest inhibitory potency. Finally, the kinetic studies indicated the inhibitory mode of compounds 1-4 against α-glucosidase were mixed types of competitive and non-competitive. Together, these findings suggested that the isolated flavonoid glycosides in this study, especially compound 4, have potential as α-glucosidase inhibitors.

Keywords: Ginkgo biloba L.; docking; kinetic analyses; α-glucosidase.

MeSH terms

  • Flavonoids* / chemistry
  • Flowers / chemistry
  • Ginkgo biloba* / chemistry
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Glycosides / chemistry
  • Kinetics
  • Molecular Docking Simulation
  • alpha-Glucosidases / metabolism

Substances

  • Flavonoids
  • Glycoside Hydrolase Inhibitors
  • Glycosides
  • alpha-Glucosidases