Membrane lipids protected from oxidation by red wine tannins: a proton NMR study

Biochimie. 2014 Dec;107 Pt A:82-90. doi: 10.1016/j.biochi.2014.07.008. Epub 2014 Jul 22.


Dietary polyphenols widespread in vegetables and beverages like red wine and tea have been reported to possess antioxidant properties that could have positive effects on human health. In this study, we propose a new in situ and non-invasive method based on proton liquid-state nuclear magnetic resonance (NMR) to determine the antioxidant efficiency of red wine tannins on a twice-unsaturated phospholipid, 1,2-dilinoleoyl-sn-glycero-3-phosphocholine (DLiPC), embedded in a membrane model. Four tannins were studied: (+)-catechin (C), (-)-epicatechin (EC), (-)-epicatechin gallate (ECG), and (-)-epigallocatechin gallate (EGCG). The lipid degradation kinetics was determined by measuring the loss of the bis-allylic protons during oxidation induced by a radical initiator, 2,2'-Azobis(2-methylpropionamidine) dihydrochloride (AAPH). The antioxidant efficiency, i.e. the ability of tannins to slow down the lipid oxidation rate, was shown to be higher for galloylated tannins, ECG and EGCG. Furthermore, the mixture of four tannins was more efficient than the most effective tannin, EGCG, demonstrating a synergistic effect. To better understand the antioxidant action mechanism of polyphenols on lipid membranes, the tannin location was investigated by NMR and molecular dynamics. A correlation between antioxidant action of tannins and their location at the membrane interface (inserted at the glycerol backbone level) could thus be established.

Keywords: Antioxidant efficiency; Lipid oxidation; Membrane location; Molecular dynamics; NMR; Tannins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Catechin / analogs & derivatives*
  • Catechin / chemistry*
  • Catechin / pharmacology
  • Chlorobenzenes / chemistry
  • Chlorobenzenes / metabolism
  • Dimyristoylphosphatidylcholine / chemistry
  • Dimyristoylphosphatidylcholine / metabolism
  • Dose-Response Relationship, Drug
  • Kinetics
  • Lipid Bilayers / chemistry
  • Lipid Bilayers / metabolism
  • Magnetic Resonance Spectroscopy
  • Membrane Lipids / chemistry*
  • Membrane Lipids / metabolism
  • Molecular Dynamics Simulation
  • Molecular Structure
  • Oxidation-Reduction / drug effects
  • Phosphatidylcholines / chemistry
  • Phosphatidylcholines / metabolism
  • Time Factors
  • Wine*


  • Antioxidants
  • Chlorobenzenes
  • Lipid Bilayers
  • Membrane Lipids
  • Phosphatidylcholines
  • Catechin
  • epicatechin gallate
  • epigallocatechin gallate
  • chlorfenethol
  • 1-palmitoyl-2-oleoylphosphatidylcholine
  • Dimyristoylphosphatidylcholine