Flavan-3-ols and procyanidins protect liposomes against lipid oxidation and disruption of the bilayer structure

Sandra V. Verstraeten, Carl L Keen, Harold H. Schmitz, César G. Fraga, Patricia I. Oteiza

Research output: Contribution to journalArticle

156 Citations (Scopus)

Abstract

The antioxidant activity and the membrane effects of the flavanols (-)-epicatechin, (+)-catechin, and their related oligomers, the procyanidins, were evaluated in liposomes composed by phosphatidylcholine:phosphatidylserine (60:40, molar ratio). When liposomes were oxidized with a steady source of free radicals, the flavanols and procyanidins (25 μM monomer equivalents) inhibited oxidation in a manner that was related to procyanidin chain length. Flavanols and procyanidins did not influence membrane fluidity or lipid lateral phase separation. However, flavanols and procyanidins induced a decrease in the membrane surface potential and protected membranes from detergent-induced disruption. These effects were dependent on flavonoid concentration, procyanidin chain length, and membrane composition. Flavanol- and procyanidin-induced inhibition of lipid oxidation was correlated with their effect on membrane surface potential and integrity. These results indicate that the interaction of flavanols and procyanidins with phospholipid head groups, particularly with those containing hydroxyl groups, is associated with a reduced rate of membrane lipid oxidation. Thus, flavanols and procyanidins can potentially reduce oxidative modifications of membranes by restraining the access of oxidants to the bilayer and the propagation of lipid oxidation in the hydrophobic membrane matrix.

Original languageEnglish (US)
Pages (from-to)84-92
Number of pages9
JournalFree Radical Biology and Medicine
Volume34
Issue number1
DOIs
StatePublished - Jan 1 2003

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Proanthocyanidins
Liposomes
Membranes
Lipids
Oxidation
Catechin
Membrane Lipids
Membrane Potentials
Chain length
Membrane Fluidity
Phosphatidylserines
Lipid Bilayers
Phosphatidylcholines
Flavonoids
Oxidants
Detergents
Hydroxyl Radical
Free Radicals
Fluidity
Phospholipids

Keywords

  • Antioxidants
  • Catechins
  • Cocoa
  • Flavonoids
  • Free radicals
  • Lipid oxidation
  • Membrane physical properties
  • Procyanidins

ASJC Scopus subject areas

  • Medicine(all)
  • Toxicology
  • Clinical Biochemistry

Cite this

Flavan-3-ols and procyanidins protect liposomes against lipid oxidation and disruption of the bilayer structure. / Verstraeten, Sandra V.; Keen, Carl L; Schmitz, Harold H.; Fraga, César G.; Oteiza, Patricia I.

In: Free Radical Biology and Medicine, Vol. 34, No. 1, 01.01.2003, p. 84-92.

Research output: Contribution to journalArticle

Verstraeten, Sandra V. ; Keen, Carl L ; Schmitz, Harold H. ; Fraga, César G. ; Oteiza, Patricia I. / Flavan-3-ols and procyanidins protect liposomes against lipid oxidation and disruption of the bilayer structure. In: Free Radical Biology and Medicine. 2003 ; Vol. 34, No. 1. pp. 84-92.
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