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.

Biological activity of phenolic lipids

“…a Anacardic acid (saturated homologue), b cardanol (alkylphenol, saturated homologue), c merulinic acid, d cardol (saturated homologue), e methylcardol (saturated homologue), f climacostol (Kieleczawa and Kozubek, unpublished data). The CMCs obtained for long-chain homologues by surface pressure measurements were lower (0.5-2.6 lM) [21]. The lipid aggregates of 3-pentadecylphenol (hydrogenated unsaturated fractions of alkylphenolic oil from CNSL) found in aqueous solution have a micellar character.…”

“…Merulinic acid induced increased permeability of liposomal vesicles depending on the composition of the liposomal bilayer and it was stronger when the lipid bilayer contained glycolipids (monogalactosyldiacylglycerol and digalactosyldiacylglycerol) and sphingomyelin [41]. Pentadecylresorcinol and cardol caused a substantial increase in calcein leakage from large unilamellar vesicles containing glycolipids (monogalactosyldiacylglycerol and digalactosyldiacylglycerol) [21].…”

“…Measurements of the alteration of fluorescence polarization of two types of membrane probes (NBD-PE and TMA-DPH) preincorporated into DPPC liposome bilayers showed that phenolic lipid molecules exhibit different and structurally dependent depths of localization in liposomal membrane. Resorcinolic lipids from rye bran and cardol from CNSL affected the properties of the hydrophobic region of the bilayer, but the properties of the subsurface part of the phospholipid bilayer were altered by anacardic acid, methylocardol, alkylphenol [21], and merulinic acid [41]. It was also found that 1-sulfate-3-myristoyl-5-pentadecylbenzene, a semisynthetic derivative of 5-npentadecylresorcinol, intensively quenched the 9-anthroyloxystearic acid signal, which suggests a relatively deep location of these molecules within the lipid bilayer [23].…”

“…Investigations using fluorescein-phosphatidylethanolamine as an indicator of surface-associated processes showed that the intensity of fluorescence of this membrane probe increases during the incorporation of anacardic acid [21] and merulinic acid [41] into egg lecithin liposomes; this effect was visible in media of both low and high ionic strength. This indicates a decrease in the local pH value at the membrane surface.…”

The Effects of Cuminum cyminum L. and Carum carvi L. Seed Extracts on Human Erythrocyte Hemolysis

“…Most antioxidants isolated from higher plants are polyphenols, which have been shown to have antibacterial, anticarcinogenic, anti-inflammatory, antiviral, antiallergic, estrogenic, and immune-stimulating biological properties (Stasiuk & Kozubek, 2008, 2010. The antioxidant activity of phenolics is mainly due to their redox properties, which allow them to act as reducing agents, hydrogen donors, singlet oxygen quenchers, and metal chelators (Ali et al, 2005).…”