Vomifoliol 9-O-α-arabinofuranosyl (1→6)-β-D-glucopyranoside from the leaves of Diospyros Kaki stimulates the glucose uptake in HepG2 and 3T3-L1 cells

Carbohydr Res. 2011 Jul 15;346(10):1212-6. doi: 10.1016/j.carres.2011.04.021. Epub 2011 Apr 21.

Abstract

A novel α-glucosidase inhibitor, vomifoliol 9-O-α-arabinofuranosyl (1→6)-β-D-glucopyranoside, was isolated for the first time from leaves of Diospyros Kaki and its bioactivity analyzed. This inhibitor exhibited strong anti-α-glucosidase activity with an IC50 value of 170.62nM and stimulated a dose-dependent increase in the uptake of a fluorescent d-glucose analog, 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-D-glucose (2-NBDG), in HepG2 cells at a rate higher than that of insulin controls. It was also found to be associated with adipocyte differentiation and moderate increases in 2-NBDG uptake by 3T3-L1 cells. These findings suggest that vomifoliol 9-O-α-arabinofuranosyl (1→6)-β-D-glucopyranoside could augment peripheral glucose as an insulin-sensitizing agent against Type 2 diabetes mellitus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells
  • 4-Chloro-7-nitrobenzofurazan / analogs & derivatives
  • 4-Chloro-7-nitrobenzofurazan / metabolism
  • Animals
  • Butanols / chemistry
  • Butanols / pharmacology*
  • Cell Differentiation / drug effects*
  • Cyclohexanols / chemistry
  • Cyclohexanols / isolation & purification
  • Cyclohexanols / pharmacology*
  • Cyclohexanones / chemistry
  • Cyclohexanones / pharmacology*
  • Deoxyglucose / analogs & derivatives
  • Deoxyglucose / metabolism
  • Diabetes Mellitus, Type 2 / metabolism
  • Diabetes Mellitus, Type 2 / pathology
  • Diospyros / metabolism*
  • Disaccharides / chemistry
  • Disaccharides / isolation & purification
  • Disaccharides / pharmacology*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolase Inhibitors*
  • Hep G2 Cells
  • Humans
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / isolation & purification
  • Hypoglycemic Agents / pharmacology*
  • Mice

Substances

  • Butanols
  • Cyclohexanols
  • Cyclohexanones
  • Disaccharides
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • vomifoliol 9-O-arabinofuranosyl-(1-6)-glucopyranoside
  • Deoxyglucose
  • 4-Chloro-7-nitrobenzofurazan
  • 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose
  • vomifoliol