Glucose-containing flavones--their synthesis and antioxidant and neuroprotective activities

Bioorg Med Chem Lett. 2009 Nov 1;19(21):6009-13. doi: 10.1016/j.bmcl.2009.09.062. Epub 2009 Sep 19.

Abstract

Due to high reactivity, reactive oxygen species can attack biological molecules leading to cell or tissue injury. In this study, glucose moiety was attached at the C-7 position of quercetin 3-O-methyl ether (1) and luteolin (2) through glycosidic bond or ether linkage. The glucose-containing compounds showed potent DPPH and superoxide anion radical scavenging and lipid peroxidation inhibition activities and nearly equivalent protective actions to the parent aglycons against the H2O2-induced oxidative neuronal damage in primary cultured rat cortical cells. Among the compounds tested, 3b and 3c were the most potent (IC50 values=7.33 and 5.34 microM, respectively), exhibiting nearly equivalent actions to the parent compounds 1 and 2 (IC50=3.50 and 3.75 microM, respectively).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cells, Cultured
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Flavones / chemical synthesis*
  • Flavones / chemistry
  • Flavones / pharmacology
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry
  • Glucosides / pharmacology
  • Hydrogen Peroxide / metabolism
  • Lipid Peroxidation
  • Luteolin / chemical synthesis*
  • Luteolin / chemistry
  • Luteolin / pharmacology
  • Neuroprotective Agents / chemical synthesis*
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology
  • Quercetin / analogs & derivatives*
  • Quercetin / chemical synthesis
  • Quercetin / chemistry
  • Quercetin / pharmacology
  • Rats
  • Reactive Oxygen Species / metabolism
  • Xanthine Oxidase / antagonists & inhibitors
  • Xanthine Oxidase / metabolism

Substances

  • Enzyme Inhibitors
  • Flavones
  • Free Radical Scavengers
  • Glucosides
  • Neuroprotective Agents
  • Reactive Oxygen Species
  • quercetin 3-O-methyl ether
  • Quercetin
  • Hydrogen Peroxide
  • Xanthine Oxidase
  • Luteolin