Membrane perturbing properties of natural phenolic and resorcinolic lipids.
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.
Department of Lipids and Liposomes, University of Wroclaw, Przybyszewskiego 63/77, 51-148 Wroclaw, Poland. stasiuk@ibmb.uni.wroc.pl
Maria
M
Stasiuk
Arkadiusz
A
Kozubek
D000818:Animals; D002463:Cell Membrane Permeability / Q000187:drug effects*; D004161:Diphenylhexatriene / Q000031:analogs & derivatives / Q000737:chemistry; D004910:Erythrocyte Membrane / Q000187:drug effects / Q000378:metabolism; D005452:Fluoresceins / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D006461:Hemolysis / Q000187:drug effects; D008051:Lipid Bilayers / Q000737:chemistry; D008055:Lipids / Q000737:chemistry / Q000494:pharmacology*; D010714:Phosphatidylethanolamines / Q000737:chemistry; D010743:Phospholipids / Q000737:chemistry; D012118:Resorcinols / Q000737:chemistry / Q000494:pharmacology*; D012434:Secale / Q000737:chemistry; D053835:Unilamellar Liposomes / Q000737:chemistry
D005452:Fluoresceins; D005456:Fluorescent Dyes; D008051:Lipid Bilayers; D008055:Lipids; D010714:Phosphatidylethanolamines; D010743:Phospholipids; D012118:Resorcinols; D053835:Unilamellar Liposomes; D004161:Diphenylhexatriene; C042077:N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)phosphatidylethanolamine; C033628:1-(4-(trimethylamino)phenyl)-6-phenylhexa-1,3,5-triene; C007740:fluorexon