Dimerization of piceatannol by Momordica charantia peroxidase and α-glucosidase inhibitory activity of the biotransformation products

Bioorg Med Chem. 2011 Sep 1;19(17):5085-92. doi: 10.1016/j.bmc.2011.07.032. Epub 2011 Jul 24.

Abstract

Stilbenes, especially those oligomers, have great potential to be antihyperglycemic agents. In this study, eight stilbene dimers, including five new ones, were obtained by biotransformation of piceatannol using Momordica charantia peroxidase (MCP) for the first time. Their structures were established on the basis of spectroscopic evidences. These piceatannol dimers displayed potential α-glucosidase inhibitory activities, and trans double bond, tetrahydrofuran ring, and free adjacent phenolic dihydroxyls were found to be important for their activities. Enzymatic biotransformation of stilbenes by M.charantia peroxidase (MCP) was showed to be a prominent way to produce oligomeric stilbenes for antihyperglycemic development.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Biotransformation
  • Dimerization
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolase Inhibitors*
  • Hypoglycemic Agents / chemistry*
  • Hypoglycemic Agents / metabolism
  • Hypoglycemic Agents / pharmacology
  • Molecular Conformation
  • Momordica charantia / enzymology*
  • Peroxidase / metabolism*
  • Stilbenes / chemistry*
  • Stilbenes / metabolism
  • Stilbenes / pharmacology
  • alpha-Glucosidases / metabolism

Substances

  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Hypoglycemic Agents
  • Stilbenes
  • 3,3',4,5'-tetrahydroxystilbene
  • Peroxidase
  • alpha-Glucosidases