Interaction of procyanidin B3 with membrane lipids - Fluorescence, DSC and FTIR studies

Biochim Biophys Acta Biomembr. 2017 Aug;1859(8):1362-1371. doi: 10.1016/j.bbamem.2017.04.026. Epub 2017 May 1.

Abstract

Procyanidins, contained in many products abundant in human diet, exhibit high biological activity. However, this activity has not been fully explained at cellular and molecular levels. In this study, we determine the mechanism of interaction of procyanidin B3 with model lipid membrane. This mechanism was established on the basis of changes induced by B3 in the physical properties of lipid bilayer. The changes were investigated using steady state and time-resolved fluorescence, DSC, and FTIR. We show that procyanidin B3 causes changes in the arrangement of the polar heads of lipids, order of their acyl chains and the main lipid phase transition temperature. Furthermore, its presence in the membrane leads to a reduction in membrane dipole potential. Procyanidin B3 is anchored to membrane via hydrogen bonds formed between its OH groups and the PO2- and CO groups of lipids, causing changes in both hydrophilic and hydrophobic regions of the membrane.

Keywords: DMPC; FTIR; Fluidity; Hydration; Order parameter; Procyanidin B(3); Procyanidin B(3) (CID 146798).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Naphthylamine / analogs & derivatives*
  • 2-Naphthylamine / chemistry
  • Biflavonoids / chemistry*
  • Calorimetry, Differential Scanning
  • Catechin / chemistry*
  • Dihydropyridines / chemistry*
  • Dimyristoylphosphatidylcholine / chemistry*
  • Hydrogen Bonding
  • Hydrophobic and Hydrophilic Interactions
  • Laurates / chemistry*
  • Lipid Bilayers / chemistry*
  • Phase Transition
  • Proanthocyanidins / chemistry*
  • Spectrometry, Fluorescence
  • Spectroscopy, Fourier Transform Infrared
  • Temperature
  • Thermodynamics

Substances

  • 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester
  • Biflavonoids
  • Dihydropyridines
  • Laurates
  • Lipid Bilayers
  • Proanthocyanidins
  • procyanidin B3
  • Catechin
  • 2-Naphthylamine
  • Dimyristoylphosphatidylcholine
  • laurdan