Potential α-glucosidase inhibitors from thermal transformation of (+)-catechin

Bioorg Med Chem Lett. 2014 Mar 15;24(6):1621-4. doi: 10.1016/j.bmcl.2014.01.027. Epub 2014 Jan 20.

Abstract

Thermal transformation of the (+)-catechin (1) with heating processing afforded a new oxidation product, gambiriin D (2), along with catechin [6'-8]-catechin (3), and (+)-epicatechin (4). The structure of a new catechin dimer with C-C linkage was determined on the basis of spectroscopic data interpretation. The catechin dimers 2 and 3 exhibited significantly improved inhibitory activities against α-glucosidase, with IC50 values of 0.16±0.2 and 0.14±0.2μM, respectively, when compared to parent (+)-catechin. Kinetic analysis showed that the two effective compounds 2 and 3 have noncompetitive modes of action.

Keywords: (+)-Catechin; (+)-Catechin dimers; Kinetic analysis; Thermal transformation; α-Glucosidase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catechin / analogs & derivatives*
  • Catechin / chemistry*
  • Catechin / metabolism
  • Dimerization
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / metabolism
  • Glycoside Hydrolase Inhibitors*
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Protein Binding
  • Stereoisomerism
  • Temperature
  • alpha-Glucosidases / metabolism

Substances

  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • catechin (6'-8)-catechin
  • gambiriin D
  • Catechin
  • alpha-Glucosidases