Effects of oleic acid and its congeners, elaidic and stearic acids, on the structural properties of phosphatidylethanolamine membranes

Funari, Sérgio S.; Barceló, Francisca; Escribá, Pablo V.

doi:10.1194/jlr.m200356-jlr200

Cited by 140 publications

(148 citation statements)

References 50 publications

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“…Using this method we estimate the radius of spontaneous curvature of α-tocopherol to be -1.52 nm from the data of Bradford et al 48 , a tight curvature that is consistent with the observation that α-tocopherol promotes the formation of Fd3m phases 49 . Similarly, we estimate the spontaneous curvature of elaidic acid to be -1.56 nm from the data of Funari et al 50 indicating that it is also a Type II lipid.…”

Section: Towards a Phenomenological Model For Determining Lipid Spontmentioning

confidence: 99%

Lipid Spontaneous Curvatures Estimated from Temperature-Dependent Changes in Inverse Hexagonal Phase Lattice Parameters: Effects of Metal Cations

et al. 2016

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Recently we reported a method for estimating the spontaneous curvatures of lipids from temperature dependent changes in the lattice parameter of inverse hexagonal liquid crystal phases of binary lipid mixtures. This method makes use of 1,2-dioleoyl-sn-glycerol-3-phosphoethanolamine, (DOPE) as a host lipid, which preferentially forms an inverse hexagonal phase, to which a guest lipid of unknown spontaneous curvature is added. The lattice parameters of these binary lipid mixtures are determined by small angle X-ray diffraction at a range of temperatures and the spontaneous curvature of the guest lipid is determined from these data. Here we report the use of this method on a wide range of lipids under different ionic conditions. We demonstrate that our method provides spontaneous curvature values for DOPE, cholesterol and monoolein that are within the range of values reported in the literature. Anionic lipids 1,2-dioleoyl-sn-glycerol-3-phosphatidic acid (DOPA) and 1,2-dioleoyl-sn-glycerol-3-phosphoserine (DOPS) were found to exhibit spontaneous curvatures that depend on the concentration of divalent cations present in the mixtures. We show that the range of curvatures estimated experimentally for DOPA and DOPS can be explained by a series of equilibria arising from lipid-cation exchange reactions. Our data indicate a universal relationship between the spontaneous curvature of a lipid and the extent to which it affects the lattice parameter of the hexagonal phase of DOPE when it is part of a binary mixture. This universal relationship affords a rapid way of estimating the spontaneous curvatures of lipids that are expensive, only available in small amounts or are of limited chemical stability.

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Section: Towards a Phenomenological Model For Determining Lipid Spontmentioning

confidence: 99%

Lipid Spontaneous Curvatures Estimated from Temperature-Dependent Changes in Inverse Hexagonal Phase Lattice Parameters: Effects of Metal Cations

et al. 2016

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“…Free fatty acids, such as oleic acid can intercalate into lipid membranes and alter their physicochemical properties [14,15]. Specifically, due to the kinked cis-double bond structure, oleic acid has been shown to alter the structure, fluidity, and permeability of saturated phospholipid monolayers and bilayers [16][17][18]. Based on monolayer studies, Gonçalves et al reported attractive lateral interactions between oleic acid and DPPC based on a decrease in the area per molecule in their mixtures at the air-water interface [19].…”

Section: Introductionmentioning

confidence: 99%

Interaction forces and membrane charge tunability: Oleic acid containing membranes in different pH conditions

Kurniawan

Suga

Kuhl

2017

Biochimica et Biophysica Acta (BBA) - Biomembranes

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Oleic acid is known to interact with saturated lipid molecules and increase the fluidity of gel phase lipid membranes. In this work, the thermodynamic properties of mixed monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and oleic acid at the air-water interface were determined using Langmuir isotherms. The isotherm study revealed an attractive interaction between oleic acid and DPPC. The incorporation of oleic acid also monotonically decreased the elastic modulus of the monolayer indicative of higher fluidity with increasing oleic acid content. Using the surface force apparatus, intermembrane force-distance profiles were obtained for substrate supported DPPC membranes containing 30 mol% oleic acid at pH 5.8 and 7.4. Three different preparation conditions resulted in distinct force profiles. Membranes prepared in pH 5.8 subphase had a low number of nanoscopic defects ≤1% and an adhesion magnitude of~0.6 mN/m. A slightly higher defect density of 1-4% was found for membranes prepared in a physiological pH 7.4 subphase. The presence of the exposed hydrophobic moieties resulted in a higher adhesion magnitude of 2.9 mN/m. Importantly, at pH 7.4, some oleic acid deprotonates resulting in a long-range electrostatic repulsion. Even though oleic acid increased the DPPC bilayer fluidity and the number of defects, no membrane restructuring was observed indicating that the system maintained a stable configuration.

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“…Recent studies showed that the activity of the adrenoreceptor signaling pathway can be regulated by oleic acid (OA) (cis-18:1n-9) (1), specifically because of the effect of this fatty acid on the structure of cell membranes (1,2). However, similar modulation of G protein-coupled receptor signaling is not induced by structurally different but closely related fatty acids with identical or similar chemical composition, such as elaidic acid (trans-18:1n-9) or stearic acid (18:0).…”

mentioning

confidence: 99%

Oleic acid content is responsible for the reduction in blood pressure induced by olive oil

Terés

Barceló‐Coblijn

Benet

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

443

266

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Numerous studies have shown that high olive oil intake reduces blood pressure (BP). These positive effects of olive oil have frequently been ascribed to its minor components, such as ␣-tocopherol, polyphenols, and other phenolic compounds that are not present in other oils. However, in this study we demonstrate that the hypotensive effect of olive oil is caused by its high oleic acid (OA) content (Ϸ70 -80%). We propose that olive oil intake increases OA levels in membranes, which regulates membrane lipid structure (HII phase propensity) in such a way as to control G protein-mediated signaling, causing a reduction in BP. This effect is in part caused by its regulatory action on G protein-associated cascades that regulate adenylyl cyclase and phospholipase C. In turn, the OA analogues, elaidic and stearic acids, had no hypotensive activity, indicating that the molecular mechanisms that link membrane lipid structure and BP regulation are very specific. Similarly, soybean oil (with low OA content) did not reduce BP. This study demonstrates that olive oil induces its hypotensive effects through the action of OA.aorta ͉ fatty acids ͉ membrane structure ͉ signaling proteins ͉ membrane-lipid therapy

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Effects of oleic acid and its congeners, elaidic and stearic acids, on the structural properties of phosphatidylethanolamine membranes

Cited by 140 publications

References 50 publications

Lipid Spontaneous Curvatures Estimated from Temperature-Dependent Changes in Inverse Hexagonal Phase Lattice Parameters: Effects of Metal Cations

Lipid Spontaneous Curvatures Estimated from Temperature-Dependent Changes in Inverse Hexagonal Phase Lattice Parameters: Effects of Metal Cations

Interaction forces and membrane charge tunability: Oleic acid containing membranes in different pH conditions

Oleic acid content is responsible for the reduction in blood pressure induced by olive oil

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