Membrane perturbing properties of natural phenolic and resorcinolic lipids

Abstract 

The effects induced by natural phenolic and resorcinolic lipids on membrane permeability were investigated. All of the compounds tested perturbed the phospholipid bilayer and stabilized erythrocytes against hypoosmotically induced hemolysis. Dipalmitoylphosphatidylcholine liposomes with two preincorporated fluorescent dyes (1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatrien p-toluenesulfonate (TMA-DPH) and N-(-nitrobenz-2-oxa-1,3-diazol-4-yl)-1,2-dihexadecanoyl-sn-glycero-3-phosphoetanolamine triethylammonium salt (NBD-PE)) were used to determine the effects of tested compounds on the core and surface of the bilayer. Resorcinolic lipids from rye and cardol increased the polarization of TMA-DPH fluorescence more than that of NBD-PE, but anacardic acid, methylocardol, and alkylphenol increased NBD-PE dye fluorescence.

Abbreviations: CMC, critical micelles concentration, CNSL, cashew nut shell liquid from Anacardium occidentale, DGDG, digalactosyldiacylglycerol, DPPC, dipalmitoylphosphatidylcholine, LUVs, large unilamellar vesicles, MGDG, monogalactosyldiacylglycerol, NBD-PE, N-(-nitrobenz-2-oxa-1,3-diazol-4-yl)-1,2-dihexadecanoyl-sn-glycero-3-phosphoetanolamine triethylammonium salt, PC, phosphatidylcholine, PE, phosphatidyletanolamine, PS, phosphatidylserine, SM, sphingomyelin, TMA-DPH, 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatrien p-toluenesulfonate, SUVs, small unilamellar vesicles

Keywords: Antihemolysis, Fluorescence polarization, Hemolysis, Permeability, Phenolic lipids, Resorcinolic lipids