Inhibition of copper-induced lipid peroxidation by sinapic acid and its derivatives in correlation to their effect on the membrane structural properties

Biochim Biophys Acta Biomembr. 2019 Jan;1861(1):1-8. doi: 10.1016/j.bbamem.2018.10.008. Epub 2018 Oct 13.

Abstract

The efficiencies of sinapic acid and its derivatives syringic acid, syringaldehyde, three sinapoyl esters (ethyl, propyl, butyl sinapates), 4-vinylsyringol and sinapine were investigated for prevention of lipid peroxidation in correlation with their interactions with model lipid membrane systems. Significant antioxidant activities of propyl and butyl sinapates were seen by fluorimetric assay in phosphatidylcholine liposomes as model membrane using C11-BODIPY581/591 lipophilic fluorescent probe. The sinapic acid esters also had the highest impact on membrane structural properties, as observed by differential scanning calorimetry and fluorescence polarisation measurements. The greatest protection of phospholipids from peroxidation by these esters correlated well with their polarity and insertion into the lipid bilayer.

Keywords: Antioxidant; Lipid peroxidation; Membrane; Sinapic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1,2-Dipalmitoylphosphatidylcholine / chemistry
  • Antioxidants / chemistry
  • Cell Membrane / chemistry*
  • Copper / chemistry*
  • Coumaric Acids / chemistry*
  • Fluorescent Dyes / chemistry
  • Free Radical Scavengers / chemistry
  • Lipid Bilayers / chemistry
  • Lipid Peroxidation / drug effects*
  • Liposomes / chemistry
  • Phosphatidylcholines / chemistry
  • Thermodynamics

Substances

  • Antioxidants
  • Coumaric Acids
  • Fluorescent Dyes
  • Free Radical Scavengers
  • Lipid Bilayers
  • Liposomes
  • Phosphatidylcholines
  • 1,2-Dipalmitoylphosphatidylcholine
  • sinapinic acid
  • Copper