Polyunsaturated fatty acid-derived chromones exhibiting potent antioxidant activity

Chem Phys Lipids. 2013 May-Jun:170-171:41-5. doi: 10.1016/j.chemphyslip.2013.03.003. Epub 2013 Mar 26.

Abstract

The marine polyunsaturated lipid-derived natural product all-(Z)-5,7-dihydroxy-2-(4Z,7Z,10Z,13Z,16Z-nonadecapentaenyl) (1) and four analogs 5-8 have been synthesized and evaluated as antioxidants in two cell-based assays. The natural product 1 and the analog 5 exhibited interesting antioxidant effects with IC50-values of 14±9 and 29±3μM, respectively, in a cellular lipid peroxidation antioxidant activity assay using HepG2 cells. Moreover, in the HepG2 cellular antioxidant activity assay, the natural product 1 exhibited strong protective effects against reactive oxygen species with an IC50=160±25μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chromones / chemical synthesis
  • Chromones / chemistry
  • Chromones / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fatty Acids, Unsaturated / chemical synthesis
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / pharmacology*
  • Hep G2 Cells
  • Humans
  • Lipid Peroxidation / drug effects
  • Molecular Structure
  • Reactive Oxygen Species / antagonists & inhibitors
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Biological Products
  • Chromones
  • Fatty Acids, Unsaturated
  • Reactive Oxygen Species