Disease relevance of oleate

• At characteristic temperatures, membranes from Escherichia coli cells enriched in exogenous elaidic acid exhibit two abrupt changes in the slope of Arrhenius plots of two enzyme activities [1].
• Ganciclovir (GCV) and its lipophilic elaidic acid ester prodrug E-GCV were evaluated for their antiherpetic, cytostatic and metabolic properties, E-GCV proved exquisitely inhibitory to the replication of herpes simplex virus type 1 (HSV-1) and HSV-2 in cell cultures (50% effective concentration (EC50): 0.002 microM) [2].
• Ether lipids have been isolated from the phospholipid fraction of Clostridium butyricum IFO 3852 cells which had been grown in media devoid of biotin with added elaidic acid or oleic acid [3].
• We employed a multiple-dose, oleic acid (OA) model to evaluate the susceptibility to oxygen toxicity of rabbits with acute lung injury (ALI) [4].
• After adjustment for established CHD risk indicators, including age, gender, cigarette smoking, hypertension and serum total cholesterol concentration, elaidic acid (P = 0.0300) and trans-10-octadecaenoic acid (P = 0.0434) were positively associated with the extent score of CAD [5].

High impact information on oleate

• When lipid synthesis and lipoprotein assembly/secretion were stimulated by adding oleic acid (OA) to the chase medium, apoB100 was deubiquitinated, and its interaction with sec61beta was disrupted, signifying completion of translocation concomitant with the formation of lipoprotein particles [6].
• In the presence of OA, when MTP lipid-transfer activity was inhibited at the end of pulse labeling, apoB100 secretion was abolished [6].
• The addition of NAC largely normalized the expression of the OA-regulated genes involved in cell growth and differentiation but not other functions [7].
• A protein kinase screen showed that OA regulated the expression and/or phosphorylation levels of kinases involved in stress-response mitogen-activated protein kinase, phosphatidylinositol 3-kinase, and cell cycle control pathways [7].
• Leaky beta-oxidation of a trans-fatty acid: incomplete beta-oxidation of elaidic acid is due to the accumulation of 5-trans-tetradecenoyl-CoA and its hydrolysis and conversion to 5-trans-tetradecenoylcarnitine in the matrix of rat mitochondria [8].

Chemical compound and disease context of oleate

• Phospholipids isolated from 25 degrees C-grown cells of strain B and from oleic acid-incorporated cells of strain K-12 UFAts had lower phase transition temperatures than did phospholipids from E. coli strain B grown at 42 degrees C or those from strain K-12 UFAts grown on elaidic acid [9].

Biological context of oleate

• The effects of oxidative stress caused by OA and potential protective effects of N-acetyl-L-cysteine (NAC), a scavenger of reactive oxygen species (ROS), on global gene expression and beta-cell function were investigated [7].
• Such micelles, consisting of oleic acid (OA), taurocholate, 2-monooleoylglycerol (2-MO), cholesterol (Chol), and L-alpha-lysophospatidylcholine, were the most efficient inducers of OA uptake and esterification [10].
• For the most severe hydrogenation condition (higher temperature and pressure, under longer reactional period), a more complete conversion of linoleic and oleic acids into stearic acid occurred with concomitant formation of the trans-species, elaidic acid (C18:1t) [11].
• We synthesized a fatty acyl-peptide derivative at aims to simultaneously activate latent TGF-beta through its peptide domain, KFK, and inhibit MMPs through its lipophilic moiety, elaidic acid [12].
• Perturbation of lipid metabolism in L-M cultured cells by elaidic acid supplementation: formation of fatty alcohols [13].

Anatomical context of oleate

• The animals were first starved to deplete adipose tissue stores and then were red a diet containing 15% of the calories as C18:1 trans fatty acid (elaidic acid) [14].
• C18:1 trans (elaidic acid) content was higher in PT and FT colostrum compared with subsequent milk samples [15].
• Three separate 1-ns simulations, with explicit solvent, are presented: 1) oleic acid (C18:1 cis) bound to adipocyte FABP, 2) oleic acid bound to human muscle FABP, and 3) elaidic acid (C18:1 trans) bound to human muscle FABP [16].
• Alteration of rat heart sarcolemma lipid composition by dietary elaidic acid [17].
• After hydrolysis of liver mitochondria PI with Naja naja phospholipase A2, we observed that elaidic acid was essentially esterified to position 1 at the expense of saturated acids, whereas cis-5,trans-9 18:2 acid was exclusively esterified to position 2, along with 20:3n-9 and 20:4n-6 acids [18].

Associations of oleate with other chemical compounds

• With oleic or linoleic acid, increases in calcium binding were observed at approximately 2-3 mol of fatty acid/mol of albumin, while for myristic, palmitic, or elaidic acid, concentrations of 5-7 fatty acids/mol of albumin were required [19].
• The main trans monoenoic acids in ruminants, elaidic acid and vaccenic acid are not found in plants [20].
• Following injection of elaidate, radioacivity of FAME was distributed between palmitate and elaidic acid indicating that rat fetal tissue may metabolize elaidic acid via beta-oxidation [21].
• Effects of dietary trielaidin upon the alkenyl chain profile of plasmalogens were studied using heart mitochondria of rats fed a semi-purified diet containing 10% of fat supplement in which elaidic acid accounted for 69% of total fatty acids [22].
• Unusual fatty acids like erucic acid, trans-oleic acid, and trans-linoleic acid can also become incorporated into the membranes of cell organelles [23].

Gene context of oleate

• The influence of elaidic acid on the plasmin/MMP-3/MMP-1 proteolytic cascade was assessed ex vivo [24].
• Activation of latent transforming growth factor beta 1 and inhibition of matrix metalloprotease activity by a thrombospondin-like tripeptide linked to elaidic acid [12].
• The increase in CETP activity was in turn significantly correlated with a fall in HDL-cholesterol among subjects during the elaidic acid-rich period (r = -0.57, P < 0.01) [25].
• Oleic acid (OA) stimulates apolipoprotein B (apoB) secretion from HepG2 cells by protecting the nascent protein from rapid intracellular degradation [26].
• The (omega;-1)/omega ratio decreased from 2.8 to 1 with lauric, myristic and palmitic acids as substrates, while the reverse was observed for unsaturated C18 fatty acids which are mainly omega-hydroxylated, except for elaidic acid showing a metabolic profile quite similar to those of saturated fatty acids [27].

Analytical, diagnostic and therapeutic context of oleate

• Microarray studies and subsequent quantitative PCR analysis showed that OA consistently regulated the expression of 45 genes involved in metabolism, cell growth, signal transduction, transcription, and protein processing [7].
• In this study, dietary trans 18:1 [elaidic acid at 5.5% energy (en)] was specifically exchanged for cis 18:1, 16:0 or 12:0 + 14:0 in 27 male and female subjects consuming moderate fat (31% en), low cholesterol (<225 mg/d) whole food diets during 4-wk diet periods in a crossover design [28].
• The mitochondrial function was better improved during simulated reperfusion with glucose than with the tested fatty acids, among which elaidic acid was the less unfavourable [29].
• Positive diagnostic patch test results for this subject and four out of five other twice-exposed study subjects suggested that the TP/OA/PG formula had a very high ACS potential [30].
• HPLC coupled to mass spectrometry for the analysis of hydroxylated metabolites of elaidic acid offers considerable advantages since the method does not require use of a radioactive molecule, completely separates the two hydroxymetabolites, confirms the identification of each metabolite, and is as sensitive as the radiometric analysis method [31].

References