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Chemical Compound Review

9-octadecenoic acid     octadec-9-enoic acid

Synonyms: Mangrove, odorless, AGN-PC-00KG6F, NCIMech_000314, AG-D-32218, ...
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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


Anatomical context of oleate


Associations of oleate with other chemical compounds


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].


  1. 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. Morrisett, J.D., Pownall, H.J., Plumlee, R.T., Smith, L.C., Zehner, Z.E. J. Biol. Chem. (1975) [Pubmed]
  2. Superior cytostatic activity of the ganciclovir elaidic acid ester due to the prolonged intracellular retention of ganciclovir anabolites in herpes simplex virus type 1 thymidine kinase gene-transfected tumor cells. Balzarini, J., Degrève, B., Andrei, G., Neyts, J., Sandvold, M., Myhren, F., de Clercq, E. Gene Ther. (1998) [Pubmed]
  3. Phase behavior of ether lipids from Clostridium butyricum. Goldfine, H., Johnston, N.C., Phillips, M.C. Biochemistry (1981) [Pubmed]
  4. Effects of hyperoxia in the presence of acute lung injury. Smith, R.A., Venus, B., Masood, S., Carter, M.C. Crit. Care Med. (1990) [Pubmed]
  5. Platelet trans fatty acids in relation to angiographically assessed coronary artery disease. Hodgson, J.M., Wahlqvist, M.L., Boxall, J.A., Balazs, N.D. Atherosclerosis (1996) [Pubmed]
  6. Apoprotein B100 has a prolonged interaction with the translocon during which its lipidation and translocation change from dependence on the microsomal triglyceride transfer protein to independence. Mitchell, D.M., Zhou, M., Pariyarath, R., Wang, H., Aitchison, J.D., Ginsberg, H.N., Fisher, E.A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  7. Gene and protein kinase expression profiling of reactive oxygen species-associated lipotoxicity in the pancreatic beta-cell line MIN6. Wang, X., Li, H., De Leo, D., Guo, W., Koshkin, V., Fantus, I.G., Giacca, A., Chan, C.B., Der, S., Wheeler, M.B. Diabetes (2004) [Pubmed]
  8. 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. Yu, W., Liang, X., Ensenauer, R.E., Vockley, J., Sweetman, L., Schulz, H. J. Biol. Chem. (2004) [Pubmed]
  9. Relationship between bactericidal action of complement and fluidity of cellular membranes. Kato, K., Bito, Y. Infect. Immun. (1978) [Pubmed]
  10. Lipid micelles stimulate the secretion of triglyceride-enriched apolipoprotein B48-containing lipoproteins by Caco-2 cells. Chateau, D., Pauquai, T., Delers, F., Rousset, M., Chambaz, J., Demignot, S. J. Cell. Physiol. (2005) [Pubmed]
  11. Method development for the analysis of trans-fatty acids in hydrogenated oils by capillary electrophoresis. de Oliveira, M.A., Solis, V.E., Gioielli, L.A., Polakiewicz, B., Tavares, M.F. Electrophoresis (2003) [Pubmed]
  12. Activation of latent transforming growth factor beta 1 and inhibition of matrix metalloprotease activity by a thrombospondin-like tripeptide linked to elaidic acid. Cauchard, J.H., Berton, A., Godeau, G., Hornebeck, W., Bellon, G. Biochem. Pharmacol. (2004) [Pubmed]
  13. Perturbation of lipid metabolism in L-M cultured cells by elaidic acid supplementation: formation of fatty alcohols. Lee, T., Hougland, A.E., Stephens, N. Biochem. Biophys. Res. Commun. (1979) [Pubmed]
  14. Incorporation of the dietary trans fatty acid (C18:1) into the serum lipids, the serum lipoproteins and adipose tissue. Schrock, C.G., Connor, W.E. Am. J. Clin. Nutr. (1975) [Pubmed]
  15. Trans fatty acids in human milk lipids: influence of maternal diet and weight loss. Chappell, J.E., Clandinin, M.T., Kearney-Volpe, C. Am. J. Clin. Nutr. (1985) [Pubmed]
  16. Simulations of fatty acid-binding proteins. II. Sites for discrimination of monounsaturated ligands. Woolf, T.B., Tychko, M. Biophys. J. (1998) [Pubmed]
  17. Alteration of rat heart sarcolemma lipid composition by dietary elaidic acid. Awad, A.B., Chattopadhyay, J.P. J. Nutr. (1983) [Pubmed]
  18. Structural importance of the cis-5 ethylenic bond in the endogenous desaturation product of dietary elaidic acid, cis-5,trans-9 18:2 acid, for the acylation of rat mitochondria phosphatidylinositol. Wolff, R.L. Lipids (1995) [Pubmed]
  19. Influence of fatty acids on the binding of calcium to human albumin. Correlation of binding and conformation studies and evidence for distinct differences between unsaturated fatty acids and saturated fatty acids. Aguanno, J.J., Ladenson, J.H. J. Biol. Chem. (1982) [Pubmed]
  20. Trans unsaturated fatty acids in natural products and processed foods. Sommerfeld, M. Prog. Lipid Res. (1983) [Pubmed]
  21. Positional specificity of trans fatty acids in fetal lecithin. Moore, C.E., Dhopeshwarkar, G.A. Lipids (1981) [Pubmed]
  22. Modification of alkenyl chain profile in plasmalogens of rat heart mitochondria by dietary trielaidin. Wolff, R.L., Combe, N.A., Entressangles, B. Lipids (1985) [Pubmed]
  23. The fatty acid composition of subcellular membranes of rat liver, heart, and brain: diet-induced modifications. Tahin, Q.S., Blum, M., Carafoli, E. Eur. J. Biochem. (1981) [Pubmed]
  24. Inhibition of plasmin-mediated prostromelysin-1 activation by interaction of long chain unsaturated fatty acids with kringle 5. Huet, E., Cauchard, J.H., Berton, A., Robinet, A., Decarme, M., Hornebeck, W., Bellon, G. Biochem. Pharmacol. (2004) [Pubmed]
  25. Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet. Abbey, M., Nestel, P.J. Atherosclerosis (1994) [Pubmed]
  26. Demonstration of biphasic effects of docosahexaenoic acid on apolipoprotein B secretion in HepG2 cells. Wu, X., Shang, A., Jiang, H., Ginsberg, H.N. Arterioscler. Thromb. Vasc. Biol. (1997) [Pubmed]
  27. Requirement for omega and (omega;-1)-hydroxylations of fatty acids by human cytochromes P450 2E1 and 4A11. Adas, F., Salaün, J.P., Berthou, F., Picart, D., Simon, B., Amet, Y. J. Lipid Res. (1999) [Pubmed]
  28. Trans (elaidic) fatty acids adversely affect the lipoprotein profile relative to specific saturated fatty acids in humans. Sundram, K., Ismail, A., Hayes, K.C., Jeyamalar, R., Pathmanathan, R. J. Nutr. (1997) [Pubmed]
  29. Substrate dependence of the postischemic cardiomyocyte recovery: dissociation between functional, metabolic and injury markers. Tissier, C., Vandroux, D., Devillard, L., Brochot, A., Moreau, D., Rochette, L., Athias, P. Mol. Cell. Biochem. (2005) [Pubmed]
  30. Evaluation of the primary skin irritation and allergic contact sensitization potential of transdermal triprolidine. Robinson, M.K., Parsell, K.W., Breneman, D.L., Cruze, C.A. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1991) [Pubmed]
  31. Liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry of omega- and (omega-1)-hydroxylated metabolites of elaidic and oleic acids in human and rat liver microsomes. Adas, F., Picart, D., Berthou, F., Simon, B., Amet, Y. J. Chromatogr. B Biomed. Sci. Appl. (1998) [Pubmed]
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