Natural and synthetic 2'-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

Bioorg Med Chem. 2009 Dec 1;17(23):8073-85. doi: 10.1016/j.bmc.2009.10.002. Epub 2009 Oct 6.

Abstract

A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Benzofurans / pharmacology
  • Biphenyl Compounds / antagonists & inhibitors
  • Biphenyl Compounds / metabolism
  • Chalcones / chemical synthesis*
  • Chalcones / chemistry
  • Chalcones / pharmacology
  • Linoleic Acid / antagonists & inhibitors
  • Linoleic Acid / metabolism
  • Lipoxygenase / metabolism*
  • Lipoxygenase Inhibitors / chemical synthesis*
  • Lipoxygenase Inhibitors / chemistry
  • Lipoxygenase Inhibitors / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Picrates / antagonists & inhibitors
  • Picrates / metabolism

Substances

  • Antioxidants
  • Benzofurans
  • Biphenyl Compounds
  • Chalcones
  • Lipoxygenase Inhibitors
  • Picrates
  • Linoleic Acid
  • 1,1-diphenyl-2-picrylhydrazyl
  • Lipoxygenase