Antioxidant and membrane effects of procyanidin dimers and trimers isolated from peanut and cocoa

Sandra V. Verstraeten, John F. Hammerstone, Carl L Keen, César G. Fraga, Patricia I. Oteiza

Research output: Contribution to journalArticle

85 Scopus citations

Abstract

The antioxidant and membrane effects of dimer (Dim) and trimer (Trim) procyanidins isolated from cocoa (Theobroma cacao) (B- and C-bonded) and peanut (Arachis hypogea L.) skin (A-bonded) were evaluated in phosphatidyl choline liposomes. When liposomes were oxidized with a steady source of oxidants, the above dimers and trimers inhibited to a similar extent lipid oxidation in a concentration (0.33-5 μM)-dependent manner. With respect to membrane effects, Dim A1, Dim B, Trim A, and Trim C increased (Dim A1 = Dim B and Trim A = Trim C), while Dim A2 decreased, membrane surface potential. All of the procyanidins tested decreased membrane fluidity as determined by fluorescent probes at the water-lipid interface, an effect that extended into the hydrophobic region of the bilayer. Both dimers and trimers protected the lipid bilayer from disruption by Triton X-100. The magnitude of the protection was Dim A1 > Dim A2 > Dim B and Trim C > Trim A. Thus, dimers and trimers can interact with membrane phospholipids, presumably with their polar headgroup. As a consequence of this interaction, they can provide protection against the attack of oxidants and other molecules that challenge the integrity of the bilayer.

Original languageEnglish (US)
Pages (from-to)5041-5048
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume53
Issue number12
DOIs
StatePublished - Jun 15 2005

Keywords

  • Antioxidants
  • Arachis hypogea L
  • Flavonoids
  • Lipid oxidation
  • Membrane interactions
  • Polyphenols
  • Procyanidins
  • Theobroma cacao

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

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