Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor

Bioorg Med Chem. 2011 Apr 1;19(7):2252-62. doi: 10.1016/j.bmc.2011.02.028. Epub 2011 Feb 24.

Abstract

Synthesis and evaluation of four diastereomers (9a, 9b, 9c and 9d) of kotalanol, a potent α-glucosidase inhibitor isolated from an Ayurvedic medicinal plant Salacia species, are described. Stereo-inversion at C-3' and C-4' of kotalanol (2) caused significant decrease of the inhibitory activities against maltase and sucrase, whereas inhibitory activity against isomaltase sustained, thus resulted in exerting selectivity against isomaltase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolase Inhibitors*
  • Molecular Structure
  • Monosaccharides / chemistry*
  • Monosaccharides / pharmacology*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfates / chemistry*
  • Sulfates / pharmacology*
  • alpha-Glucosidases / chemistry*
  • alpha-Glucosidases / metabolism

Substances

  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Kotalanol
  • Monosaccharides
  • Plant Extracts
  • Sulfates
  • alpha-Glucosidases