Lignan Constituents from the Fruits of Viburnum macrocephalum f. keteleeri and Their α-Amylase, α-Glucosidase, and Protein Tyrosine Phosphatase 1B Inhibitory Activities

J Agric Food Chem. 2020 Oct 7;68(40):11151-11160. doi: 10.1021/acs.jafc.0c03353. Epub 2020 Sep 23.

Abstract

Eight previously undescribed lignan glycosides, viburmacrosides A-H (1-8), and seven known analogues (9-15) were isolated from Viburnum macrocephalum f. keteleeri fruits through bioactivity-guided fractionation. Their structures and absolute configurations were elucidated by extensive spectroscopic analyses and chemical evidence. Using the well-recognized carbohydrate-hydrolyzing enzymes α-amylase and α-glucosidase, as well as the promising protein tyrosine phosphatase 1B (PTP1B), as inhibitory targets, all isolated compounds were tested for their antidiabetic potential in vitro. Compound 4 displayed potent inhibitory activities with IC50 values of 9.9 ± 0.6 and 8.9 ± 0.5 μM against α-glucosidase and PTP1B, respectively. The enzymatic kinetics results suggested that compound 4 competitively inhibited α-glucosidase while it suppressed α-amylase and PTP1B in the mixed-type manner. These findings supported that V. macrocephalum f. keteleeri fruits may be a new functional food resource with antidiabetic potential.

Keywords: Caprifoliaceae; PTP1B; Viburnum macrocephalum f. keteleeri fruits; lignans; α-amylase; α-glucosidase.

MeSH terms

  • Enzyme Inhibitors / chemistry*
  • Fruit / chemistry
  • Glycoside Hydrolase Inhibitors / chemistry
  • Humans
  • Hypoglycemic Agents / chemistry
  • Kinetics
  • Lignans / chemistry*
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / chemistry
  • Viburnum / chemistry*
  • alpha-Amylases / antagonists & inhibitors*
  • alpha-Amylases / chemistry
  • alpha-Glucosidases / chemistry

Substances

  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • Lignans
  • Plant Extracts
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1
  • alpha-Amylases
  • alpha-Glucosidases