Disease relevance of oleic acid

• Influenza virus did not alter membrane fluidity as measured by electron spin resonance spectroscopy with the probe 5-doxyl stearate [1].
• From these results we conclude that the major structural transition at 30-31 degrees C observed previously with 5-, 12-, and 16-doxyl stearate in intact E. coli membranes is due to the DEPE present (Morrisett, J.D., Pownall, H.J., Plumlee, R.T., Smith, L.C., Zehner, Z.E., Esfahani, M., and Wakil, S.J. (1975) J. Biol. Chem. 250, 6969-6976) [2].
• Stearate inhibition of breast cancer cell proliferation. A mechanism involving epidermal growth factor receptor and G-proteins [3].
• In the absence of SCD1, stearate promotes oxidation, leading to protection from saturated fat-induced obesity [4].
• Muscle palmityl CoA (16:0; 0.54 +/- 0.08 vs. 0.35 +/- 0.04 nmol/g wet wt) concentration decreased by approximately 35% (P < 0.05) with weight loss, whereas stearate CoA (18:0; -17%; 0.65 +/- 0.05 vs. 0.54 +/- 0.03 nmol/g wet wt) and linoleate CoA (18:2; -30%; 2.47 +/- 0.27 vs. 1.66 +/- 0.19 nmol/g wet wt) were also reduced (P < 0.05) [5].

Psychiatry related information on oleic acid

• The reaction time after administration of the pellets is significantly longer than after the stearate or ethylsuccinate formulations [6].
• Dental anxiety and the absorption of orally administered erythromycin stearate [7].

High impact information on oleic acid

• This pattern of FA distribution was observed regardless of the type of nonalbumin acceptor used (phospholipid vesicles, human high- or low-density lipoproteins) or the type of FA used (palmitate, oleate, or stearate), and provided evidence for negative cooperativity for human serum albumin upon binding of 1 mol of FA per mole albumin [8].
• The gallbladder contracted to 42 (3)% of its initial volume after oleate but remained at 89 (8)% of its initial volume after stearate [9].
• The Garm FatA1, an acyl-acyl carrier protein (ACP) thioesterase isolated from Garcinia mangostana, generates an elevated stearate (18:0) phenotype in transgenic Brassica plants [10].
• Improved stearate phenotype in transgenic canola expressing a modified acyl-acyl carrier protein thioesterase [10].
• The spin label, 12-doxyl stearate, was incorporated into these membranes [11].

Chemical compound and disease context of oleic acid

• Multiple thermotropic phase transitions in Escherichia coli membranes and membrane lipids. A comparison of results obtained by nitroxyl stearate paramagnetic resonance, pyrene excimer fluorescence, and enzyme activity measurements [12].
• Plasma and sputum concentrations of erythromycin were measured in 10 patients with chronic bronchitis during an eight-day course of a new formulation of erythromycin stearate [13].
• Tri-iodothyronine treatment (25 micrograms/100 g body weight) daily for 3 weeks caused no significant changes in delta 9 (stearate) desaturation but a 24% decrease in delta 6 (linoleate) desaturation [14].
• Rapid production of diacylglycerols enriched in arachidonate and stearate during early brain ischemia [15].
• The cellular fatty acid compositions of all the Plesiomonas strains were identical and characterized by the presence of hexadecanoate (16:0) (33%), hexadecenoate (16:1) (28%), octadecenoate (18:1) (9%), and octadecanoate (18:0) (6%) [16].

Biological context of oleic acid

• The plants with the altered stearate phenotype were shown to express ribozyme RNA [17].
• Treatment of HCAECs with saturated NEFAs (palmitate and stearate) increased apoptosis up to fivefold (P < 0.05; n = 4) [18].
• In contrast, stearate had little effect on insulin-like growth factor-1-stimulated cell proliferation [3].
• The kinetics of competitive inhibition for transport of oleate and stearate are shown under conditions where complications due to competition for binding of FAs to the albumin in the medium are minimized [19].
• These results indicate that the desaturation of saturated fats such as stearate by SCD is an essential step mediating their induction of lipogenesis [4].

Anatomical context of oleic acid

• To characterize alterations in membrane molecular dynamics produced by amphiphilic compounds, highly purified preparations of canine myocardial sarcolemma were spin-labeled with paramagnetic probes (5-, 12-, or 16-doxyl stearate), and alterations produced by amphiphilic compounds were quantified by electron spin resonance spectroscopy [20].
• Rat hepatocyte plasma membranes were isolated and examined by differential scanning calorimetry and by steady state fluorescence polarization of 1,6-diphenyl-1,3,5-hexatriene, 12-anthroyl stearate, and 2-anthroyl stearate [21].
• In this report we describe a study of beta-oxidation of palmitate and stearate using HepG2 cells cultured in the presence of multiple concentrations of [U-(13)C(18)]stearate or [U-(13)C(16)] palmitate [22].
• Mitochondrial fatty acid oxidation is increased, and white adipose tissue and hepatic glycogen stores are depleted in stearate-fed Scd1(-/-) mice [4].
• The distribution of a lipophilic spin probe, 5-doxyl stearate, between the inner and outer halves of the sarcoplasmic reticulum (SR) bilayer was determined by titration with Ni X EDTA, a spin broadening agent [23].

Associations of oleic acid with other chemical compounds

• Unsaturated NEFAs (palmitoleate, oleate, and linoleate) did not promote apoptosis but prevented stearate-induced apoptosis (P < 0.05; n = 4) [18].
• Gas-liquid chromatography of the fatty acids released from PO showed labeling of methyl esters of palmitate, stearate, and oleate (56, 16, and 5%, respectively) [24].
• Neither stearate, methyl stearate, spin-labeled methyl stearates nor 2,2,6,6,-tetramethylpiperidine-1-oxyl (Tempo) altered cell viability or enzyme activities at the concentrations studied [25].
• Chain shortening of stearate in peroxisomes generates acetyl-CoA, which is subsequently used in the chain elongation of a second stearate molecule to form very long chain fatty acids [22].
• In the nonreducing DAG, the octadecanoic acid is attached to the 3-hydroxy group of 3-hydroxytetradecanoic acid [26].

Gene context of oleic acid

• However, in Scd1(-/-) mice, stearate does not induce lipogenesis, and Srebp-1c and Pgc-1beta levels are markedly reduced [4].
• Pretreatment of cells with 0.15 mmol/L stearate from 0 to 6 hours inhibits, in parallel, both the EGF-induced cell proliferation and pertussis-toxin-catalyzed ADP ribosylation of the G-protein associated with the EGFR [3].
• Whereas myristate, palmitate, stearate, oleate and linoleate stimulated CETP activity to varying extents, all NEFAs suppressed LTIP activity [27].
• The quantities of retinyl esters (mainly stearate and palmitate in the ratio of 6:1, respectively) stored in dark-adapted mouse eyes progressively increased as the animals aged, representing 0.5 mole eq. of the rhodopsin at 8 months [28].
• Certain phosphoinositides also stimulated Tiam1 activity but were less potent than ascorbyl stearate [29].

Analytical, diagnostic and therapeutic context of oleic acid

• Structural analysis by NMR, mass spectrometry, and x-ray crystallography indicated that the rabbit liver inhibitor was a fatty acid ester (mostly stearate) of a pentacyclic triterpene acid [30].
• The uptake of [(3)H]oleic acid and [(3)H]stearic acid into HepG2 cells was measured by radioactive assays and internalization of the non-metabolizable fluorescent fatty acid 12-(N-methyl)-N-[(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino] (12-NBD) stearate into single HepG2 cells was semi-quantitatively assessed by laser scanning microscopy [31].
• The LDI mass spectrum of the collected HPLC fraction of rat liver extract showed the molecular parent ions of retinyl myristate, pentadecanoate, palmitoleate, palmitate, heptadecanoate, linoleate, oleate, stearate, and 3,4-didehydroretinyl palmitate [32].
• Comparison of the ESR 2T(||) values (the splitting between low and high field extremes, a measure of the degree of immobilization of protein-bound spin-label stearate) for bovine and human albumin indicates a greater immobilization of the spin-label molecules bound to human albumin [33].
• 2. Ultracentrifugation of the ruptured plastids at 105000g gave a supernatant that formed mainly stearate from [2-14C]malonyl-CoA and to a lesser extent from [1-14C]acetate [34].

References