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Chemical Compound Review

oleate     (Z)-octadec-9-enoic acid

Synonyms: Elaidate, Metaupon, Oleinate, Distoline, Elaidoate, ...
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Disease relevance of oleic acid


Psychiatry related information on oleic acid

  • Activation of protein kinase C by sodium oleate required the presence of calcium and showed mild cooperative behavior (Hill number of 1.25) suggesting that Ca(oleate)2 is the active species [6].
  • CONCLUSIONS: With the use of multiple injections of oleic acid, a stable model of early respiratory distress in pigs can be achieved, in spite of individual differences in sensitivity [7].
  • BACKGROUND AND AIMS: Numerous studies suggest n -3 polyunsaturated fatty acids (n -3 PUFA) and oleic acid intake have beneficial effects on health including risk reduction of coronary heart disease [8].
  • This method has been optimized and the optimum enzyme incubation time and reaction time of the generated oleic acid with ADAM were both at 20 min [9].
  • Using the defined optimal conditions, the conversion reaction was scaled up in a stirred-batch reactor by using technical-grade oleic acid as substrate [10].

High impact information on oleic acid

  • We placed 34 women (mean age, 26 years) and 25 men (mean age, 25 years) on three mixed natural diets of identical nutrient composition, except that 10 percent of the daily energy intake was provided as oleic acid (which contains one cis double bond), trans isomers of oleic acid, or saturated fatty acids [11].
  • As few as four amino acid substitutions can convert an oleate 12-desaturase to a hydroxylase and as few as six result in conversion of a hydroxylase to a desaturase [12].
  • Rat electroretinograms were measured as a function of dietary supplements of purified ethyl esters of linolenic acid, linoleic acid, and oleic acid [13].
  • In contrast, cell membrane levels of trans-18:1 (trans-isomers of oleic acid), the major TFA in foods, do not appear associated with higher risk of SCD [14].
  • When a mixture of TFA isomers obtained by partial hydrogenation of vegetable oils is used to replace oleic acid, there is a dose-dependent increase in the LDL:HDL ratio [15].

Chemical compound and disease context of oleic acid

  • We investigated the effects of oleic acid and linoleic acid on transplanted Ehrlich ascites carcinoma and Ehrlich solid carcinoma in ACR mice [16].
  • METHODS: One hundred sixteen consecutive cirrhotic patients admitted because of variceal bleeding were randomly allocated to either continuous administration of propranolol to reduce the resting heart rate by 25% (58 patients) or weekly intravariceal sclerotherapy sessions using 5% ethanolamide oleate until varices disappeared (58 patients) [17].
  • In four dogs prepared with chronic gastric fistula and colonic fistula in the cecum the effects on pentagastrin dose responses of colonic perfusion with the following substance were studied: saline, 15% liver extract pH 7.0; sodium oleate pH 9.4; and 0.08 M HCl [18].
  • In cardiac tissue the concentrations of oleic acid, arachidonic acid, leukotrienes, and other fatty acids increase greatly during ischemia due to receptor or nonreceptor-mediated activation of phospholipases and/or diminished reacylation [19].
  • This observation correlates strikingly with the long-known effect of 3-decynoyl-N-acetylcysteamine, a "suicide analog" that prevents initiation of a cycle of replication in E. coli by inhibiting the synthesis of oleic acid, an inhibition that can be overcome by providing the cells with oleic acid [20].

Biological context of oleic acid

  • Incubation with AcLDL but not LDL leads to a marked stimulation of cholesterol esterification, as measured by labeled oleic acid incorporation into cholesteryl esters, and a concomitant increase in cellular cholesteryl ester content [21].
  • Hence, under the experimental conditions employed in this study using a variety of suspended cell types, oleate uptake kinetics were consistent with the conventional theory at physiologic concentrations of albumin [22].
  • Oleate uptake by cardiac myocytes is carrier mediated and involves a 40-kD plasma membrane fatty acid binding protein similar to that in liver, adipose tissue, and gut [23].
  • (c) Mass VLDL-TG secretion by cultured apo E-deficient hepatocytes was reduced by 23% compared with control values in serum-free medium, and by 61% in the presence of oleate in medium (0. 75 mM) to stimulate lipogenesis [24].
  • (5) During the time of plateau 14CO2 release, oleic acid extracted from plasma could account for only 20% of oxygen consumption; most of the oleic acid taken up was not oxidized directly [25].

Anatomical context of oleic acid

  • [3H]-cholesteryl oleate-labeled small unilamellar liposomes, which are rapidly endocytosed by hepatocytes, were intravenously injected to label intrahepatic cholesterol pools, and plasma and bile were collected [26].
  • When [14C]oleate alone or compounded with bovine serum albumin at various molar ratios was incubated with MVM aliquots, binding was time- and temperature-dependent, inhibitable by addition of excess cold oleate, and decreased by heat denaturation or trypsin digestion of the membranes [27].
  • To reexamine the role of albumin in cellular uptake of long chain fatty acids, we measured [3H]oleate uptake by isolated hepatocytes, adipocytes, and cardiac myocytes from incubations containing oleate/albumin complexes at molar ratios from 0.01:1 to 2:1 [22].
  • Effects of dihydroxy bile acids and hydroxy fatty acids on the absorption of oleic acid in the human jejunum [28].
  • Hypertrophied myocytes exhibited reduced capacity for cellular lipid homeostasis, as evidenced by intracellular fat accumulation in response to oleate loading [29].

Associations of oleic acid with other chemical compounds

  • In addition, gas-chromatography analysis of tumor cell lipids showed that appreciable changes occurred in the fatty acid composition of the tumor cell grown in mice treated with oleic acid or linoleic acid [16].
  • The data demonstrated that a high percentage (84 +/- 17%) of the palmitate and oleate extracted by the myocardium underwent rapid oxidation [30].
  • Adding 125 muM oleate to isolated rat pancreatic islets cultured with 5.6 mM glucose caused a 50% fall in their insulin content over 24 h, coupled with a marked enhancement of basal insulin secretion [31].
  • HPLC analysis of lymph at 6, 10, 12, and 14.5 h of infusion showed a progressive rise in TG composed of one linoleate and two oleates, to 39%; and in TG composed of two linoleates and one oleate to 20% at 14.5 h of infusion [32].
  • For evaluation of the promotional effects of dietary trans-fatty acids on large intestinal carcinogenesis, 120 inbred female F344 rats were divided into 6 groups and fed a 25% elaidic acid diet, a 25% oleic acid diet, or a regular (4.5% fat) chow diet [33].

Gene context of oleic acid

  • Ant1p was found to be an integral protein of the peroxisomal membrane and expression of ANT1 was oleic acid inducible [34].
  • Gel blot analyses of FAD2 mRNA levels showed that the gene is expressed throughout the plant and suggest that transcript levels are in excess of the amount needed to account for oleate desaturation [35].
  • A mutation in the Arabidopsis gene ssi2/fab2, which encodes stearoyl-acyl carrier protein desaturase (S-ACP-DES), results in the reduction of oleic acid (18:1) levels in the mutant plants and also leads to the constitutive activation of NPR1-dependent and -independent defense responses [36].
  • Disruption of PXA1 results in impaired growth on oleic acid and reduced ability to oxidize oleate [37].
  • A screening strategy has been developed and used to identify eight S. cerevisiae mutants, from three complementation groups, that are defective in the oleate induction of POX1 [38].

Analytical, diagnostic and therapeutic context of oleic acid


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  2. Alveolar epithelial damage. A critical difference between high pressure and oleic acid-induced low pressure pulmonary edema. Montaner, J.S., Tsang, J., Evans, K.G., Mullen, J.B., Burns, A.R., Walker, D.C., Wiggs, B., Hogg, J.C. J. Clin. Invest. (1986) [Pubmed]
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  6. Regulation of platelet protein kinase C by oleic acid. Kinetic analysis of allosteric regulation and effects on autophosphorylation, phorbol ester binding, and susceptibility to inhibition. el Touny, S., Khan, W., Hannun, Y. J. Biol. Chem. (1990) [Pubmed]
  7. A stable model of respiratory distress by small injections of oleic acid in pigs. Grotjohan, H.P., van der Heijde, R.M., Jansen, J.R., Wagenvoort, C.A., Versprille, A. Intensive care medicine. (1996) [Pubmed]
  8. n-3 Fatty acids plus oleic acid and vitamin supplemented milk consumption reduces total and LDL cholesterol, homocysteine and levels of endothelial adhesion molecules in healthy humans. Baró, L., Fonollá, J., Peña, J.L., Martínez-Férez, A., Lucena, A., Jiménez, J., Boza, J.J., López-Huertas, E. Clinical nutrition (Edinburgh, Scotland) (2003) [Pubmed]
  9. Analysis of lipoprotein lipase activity using high-performance liquid chromatography. Eguchi, Y. Biomed. Chromatogr. (2002) [Pubmed]
  10. Conversion of fatty acids by Bacillus sphaericus-like organisms. Kuo, T.M., Nakamura, L.K., Lanser, A.C. Curr. Microbiol. (2002) [Pubmed]
  11. Effect of dietary trans fatty acids on high-density and low-density lipoprotein cholesterol levels in healthy subjects. Mensink, R.P., Katan, M.B. N. Engl. J. Med. (1990) [Pubmed]
  12. Catalytic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids. Broun, P., Shanklin, J., Whittle, E., Somerville, C. Science (1998) [Pubmed]
  13. Visual membranes: specificity of fatty acid precursors for the electrical response to illumination. Wheeler, T.G., Benolken, R.M., Anderson, R.E. Science (1975) [Pubmed]
  14. Trans-fatty acids and sudden cardiac death. Lemaitre, R.N., King, I.B., Mozaffarian, D., Sootodehnia, N., Siscovick, D.S. Atherosclerosis. Supplements. (2006) [Pubmed]
  15. Trans fatty acids and blood lipids. Ascherio, A. Atherosclerosis. Supplements. (2006) [Pubmed]
  16. Growth-inhibition effects of oleic acid, linoleic acid, and their methyl esters on transplanted tumors in mice. Zhu, Y.P., Su, Z.W., Li, C.H. J. Natl. Cancer Inst. (1989) [Pubmed]
  17. Propranolol versus sclerotherapy in preventing variceal rebleeding: a randomized controlled trial. Terés, J., Bosch, J., Bordas, J.M., Garcia Pagán, J.C., Feu, F., Cirera, I., Rodés, J. Gastroenterology (1993) [Pubmed]
  18. Colonic inhibition of gastric acid secretion in the dog. Seal, A.M., Debas, H.T. Gastroenterology (1980) [Pubmed]
  19. Long-chain fatty acids activate calcium channels in ventricular myocytes. Huang, J.M., Xian, H., Bacaner, M. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  20. Membrane attachment activates dnaA protein, the initiation protein of chromosome replication in Escherichia coli. Yung, B.Y., Kornberg, A. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  21. Receptor activities for low-density lipoprotein and acetylated low-density lipoprotein in a mouse macrophage cell line (IC21) and in human monocyte-derived macrophages. Traber, M.G., Defendi, V., Kayden, H.J. J. Exp. Med. (1981) [Pubmed]
  22. At physiologic albumin/oleate concentrations oleate uptake by isolated hepatocytes, cardiac myocytes, and adipocytes is a saturable function of the unbound oleate concentration. Uptake kinetics are consistent with the conventional theory. Sorrentino, D., Robinson, R.B., Kiang, C.L., Berk, P.D. J. Clin. Invest. (1989) [Pubmed]
  23. Oleate uptake by cardiac myocytes is carrier mediated and involves a 40-kD plasma membrane fatty acid binding protein similar to that in liver, adipose tissue, and gut. Sorrentino, D., Stump, D., Potter, B.J., Robinson, R.B., White, R., Kiang, C.L., Berk, P.D. J. Clin. Invest. (1988) [Pubmed]
  24. Impaired secretion of very low density lipoprotein-triglycerides by apolipoprotein E- deficient mouse hepatocytes. Kuipers, F., Jong, M.C., Lin, Y., Eck, M., Havinga, R., Bloks, V., Verkade, H.J., Hofker, M.H., Moshage, H., Berkel, T.J., Vonk, R.J., Havekes, L.M. J. Clin. Invest. (1997) [Pubmed]
  25. Free fatty acid oxidation by forearm muscle at rest, and evidence for an intramuscular lipid pool in the human forearm. Dagenais, G.R., Tancredi, R.G., Zierler, K.L. J. Clin. Invest. (1976) [Pubmed]
  26. Dietary fish oil-induced changes in intrahepatic cholesterol transport and bile acid synthesis in rats. Smit, M.J., Temmerman, A.M., Wolters, H., Kuipers, F., Beynen, A.C., Vonk, R.J. J. Clin. Invest. (1991) [Pubmed]
  27. Identification, isolation, and partial characterization of a fatty acid binding protein from rat jejunal microvillous membranes. Stremmel, W., Lotz, G., Strohmeyer, G., Berk, P.D. J. Clin. Invest. (1985) [Pubmed]
  28. Effects of dihydroxy bile acids and hydroxy fatty acids on the absorption of oleic acid in the human jejunum. Wanitschke, R., Ammon, H.V. J. Clin. Invest. (1978) [Pubmed]
  29. Deactivation of peroxisome proliferator-activated receptor-alpha during cardiac hypertrophic growth. Barger, P.M., Brandt, J.M., Leone, T.C., Weinheimer, C.J., Kelly, D.P. J. Clin. Invest. (2000) [Pubmed]
  30. Myocardial metabolism of free fatty acids. Studies with 14C-labeled substrates in humans. Wisneski, J.A., Gertz, E.W., Neese, R.A., Mayr, M. J. Clin. Invest. (1987) [Pubmed]
  31. Chronic exposure to free fatty acid reduces pancreatic beta cell insulin content by increasing basal insulin secretion that is not compensated for by a corresponding increase in proinsulin biosynthesis translation. Bollheimer, L.C., Skelly, R.H., Chester, M.W., McGarry, J.D., Rhodes, C.J. J. Clin. Invest. (1998) [Pubmed]
  32. Mechanism of lipid mobilization by the small intestine after transport blockade. Halpern, J., Tso, P., Mansbach, C.M. J. Clin. Invest. (1988) [Pubmed]
  33. Large intestinal carcinogenesis. I. Promotional effect of dietary fatty acid isomers in the rat model. Hogan, M.L., Shamsuddin, A.M. J. Natl. Cancer Inst. (1984) [Pubmed]
  34. Identification and functional reconstitution of the yeast peroxisomal adenine nucleotide transporter. Palmieri, L., Rottensteiner, H., Girzalsky, W., Scarcia, P., Palmieri, F., Erdmann, R. EMBO J. (2001) [Pubmed]
  35. Arabidopsis FAD2 gene encodes the enzyme that is essential for polyunsaturated lipid synthesis. Okuley, J., Lightner, J., Feldmann, K., Yadav, N., Lark, E., Browse, J. Plant Cell (1994) [Pubmed]
  36. Plastidial fatty acid signaling modulates salicylic acid- and jasmonic acid-mediated defense pathways in the Arabidopsis ssi2 mutant. Kachroo, A., Lapchyk, L., Fukushige, H., Hildebrand, D., Klessig, D., Kachroo, P. Plant Cell (2003) [Pubmed]
  37. PXA1, a possible Saccharomyces cerevisiae ortholog of the human adrenoleukodystrophy gene. Shani, N., Watkins, P.A., Valle, D. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  38. A complex containing two transcription factors regulates peroxisome proliferation and the coordinate induction of beta-oxidation enzymes in Saccharomyces cerevisiae. Karpichev, I.V., Luo, Y., Marians, R.C., Small, G.M. Mol. Cell. Biol. (1997) [Pubmed]
  39. Effect of growth hormone-release inhibiting hormone on hormones stimulating exocrine pancreatic secretion. Konturek, S.J., Tasler, J., Obtulowicz, W., Coy, D.H., Schally, A.V. J. Clin. Invest. (1976) [Pubmed]
  40. Turnover and splanchnic metabolism of free fatty acids in hyperthyroid patients. Hagenfeldt, L., Wennlung, A., Felig, P., Wahren, J. J. Clin. Invest. (1981) [Pubmed]
  41. Effects of monoclonal antibodies to somatostatin on somatostatin-induced and intestinal fat-induced inhibition of gastric acid secretion in the rat. Seal, A.M., Meloche, R.M., Liu, Y.Q., Buchan, A.M., Brown, J.C. Gastroenterology (1987) [Pubmed]
  42. Peptide YY inhibits pancreatic secretion by inhibiting cholecystokinin release in the dog. Lluis, F., Gomez, G., Fujimura, M., Greeley, G.H., Thompson, J.C. Gastroenterology (1988) [Pubmed]
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