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Chemical Compound Review

Hystrene     octadecanoic acid

Synonyms: Stearate, Dermarone, Vanicol, Industrene, Prodhygine, ...
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Disease relevance of oleic acid


High impact information on oleic acid


Chemical compound and disease context of oleic acid


Biological context of oleic acid

  • To identify the active site in VIP, over 50 related fragments containing an N-terminal stearic acid attachment and an amidated C terminus were designed, synthesized, and tested for neuroprotective properties [16].
  • Membrane fluidity was assessed by electron spin resonance (ESR) using a nitroxide-substituted stearic acid analog (5DS) as a spin probe [17].
  • Since the interconversion of the input [3H]palmitic acid to stearic acid is even lower in CV1 cells than in insect cells, it follows that only HEF expressed in mammalian, but not in insect cells selects for stearic acid during its biosynthetic acylation [18].
  • Benzophenone (BP) was used as a photosensitizer to initiate lipid peroxidation in model and native biological membranes at concentrations of BP that do not perturb bilayer structure, as assessed by stearic acid spin label dynamics [19].
  • The resulting down-regulation of the ghSAD-1 gene substantially increased stearic acid from the normal levels of 2% to 3% up to as high as 40%, and silencing of the ghFAD2-1 gene resulted in greatly elevated oleic acid content, up to 77% compared with about 15% in seeds of untransformed plants [20].

Anatomical context of oleic acid

  • Depolymerization of microtubules resulted in an increase in the motional freedom of molecular probes in the plasma membranes of Chinese hamster ovary cells expressed by the order parameter, S, measured with two different lipid-soluble spin label probes, 5-doxyl stearic acid and 16-doxyl methylstearate [21].
  • Enrichment of the fatty acyl chains with elaidate or the polar headgroups with PE also inhibits fusion, but in contrast to that by 25-OH cholesterol, a significant fraction of the myoblasts are aligned and interacting with each other [22].
  • After mitogen stimulation, fatty acid uptake was increased in both lymphocyte types, but cell-specific differences were seen in the distribution of stearic acid among the various cellular lipids [23].
  • Stearic acid is toxic for T lymphocytes in vitro but has little effect on B lymphocytes [23].
  • Unstimulated T and B cells incorporated identical amounts of stearic acid into six different phospholipids and four neutral lipids [23].

Associations of oleic acid with other chemical compounds


Gene context of oleic acid

  • The fatty acids that accumulate in livers of SREBP transgenic mice are 18 carbons rather than 16 carbons in length, suggesting that the enzymes required for the elongation of palmitic to stearic acid may be induced [29].
  • Both UFAs are formed in S. cerevisiae by the oxygen- and NADH-dependent desaturation of palmitic acid (C(16:0)) and stearic acid (C(18:0)), respectively, catalyzed by a single integral membrane desaturase encoded by the OLE1 gene [30].
  • The findings of this study reveal that IFN-gamma might act on the enzymes controlling the labelling of the sn2 position of phospholipids (linoleic acid) but not the sn1 position (stearic acid), and this increases the polyunsaturated fatty acid content of macrophage membranes [31].
  • The current studies suggest that mouse LCE expression is increased by SREBPs and that the enzyme is a component of the elusive mammalian elongation system that converts palmitic to stearic acid [29].
  • On normal rodent chow, Cyp27(-/-) mice have 40% larger livers, 45% larger adrenals, 2-fold higher hepatic and plasma triacylglycerol concentrations, a 70% higher rate of hepatic fatty acid synthesis, and a 70% increase in the ratio of oleic to stearic acid in the liver versus Cyp27(+/+) controls [32].

Analytical, diagnostic and therapeutic context of oleic acid


  1. Cytochalasin delays but does not prevent cell death from anoxia. Okayasu, T., Curtis, M.T., Farber, J.L. Am. J. Pathol. (1984) [Pubmed]
  2. Arachidonic acid and docosahexaenoic acid are increased in human colorectal cancer. Neoptolemos, J.P., Husband, D., Imray, C., Rowley, S., Lawson, N. Gut (1991) [Pubmed]
  3. Structural identification of the lipo-chitin oligosaccharide nodulation signals of Rhizobium loti. López-Lara, I.M., van den Berg, J.D., Thomas-Oates, J.E., Glushka, J., Lugtenberg, B.J., Spaink, H.P. Mol. Microbiol. (1995) [Pubmed]
  4. Fatty acids in animals: thrombosis and hemostasis. Hoak, J.C. Am. J. Clin. Nutr. (1997) [Pubmed]
  5. Stearic acid metabolism and atherogenesis: history. Kritchevsky, D. Am. J. Clin. Nutr. (1994) [Pubmed]
  6. Effect of dietary stearic acid on plasma cholesterol and lipoprotein levels. Bonanome, A., Grundy, S.M. N. Engl. J. Med. (1988) [Pubmed]
  7. Scrapie prion protein contains a phosphatidylinositol glycolipid. Stahl, N., Borchelt, D.R., Hsiao, K., Prusiner, S.B. Cell (1987) [Pubmed]
  8. A fatty neuropeptide. Potential drug for noninvasive impotence treatment in a rat model. Gozes, I., Fridkin, M. J. Clin. Invest. (1992) [Pubmed]
  9. Ursodeoxycholate stimulates Na+-H+ exchange in rat liver basolateral plasma membrane vesicles. Moseley, R.H., Ballatori, N., Smith, D.J., Boyer, J.L. J. Clin. Invest. (1987) [Pubmed]
  10. Correlation between the ability of tumor cells to incorporate specific fatty acids and their sensitivity to killing by a specific antibody plus guinea pig complement. Schlager, S.I., Ohanian, S.H., Borsos, T. J. Natl. Cancer Inst. (1978) [Pubmed]
  11. Structural changes in BHK cell plasma membrane caused by the binding of vesicular stomatitis virus. Altstiel, L.D., Landsberger, F.R. J. Virol. (1981) [Pubmed]
  12. Mechanism of arachidonic acid liberation during ischemia in gerbil cerebral cortex. Abe, K., Kogure, K., Yamamoto, H., Imazawa, M., Miyamoto, K. J. Neurochem. (1987) [Pubmed]
  13. Evaluation of a novel, anti-herpes simplex virus compound, acyclovir elaidate (P-4010), in the female guinea pig model of genital herpes. Jennings, R., Smith, T.L., Myhren, F., Phillips, J., Sandvold, M.L. Antimicrob. Agents Chemother. (1999) [Pubmed]
  14. The hemagglutinating glycoproteins of influenza B and C viruses are acylated with different fatty acids. Veit, M., Herrler, G., Schmidt, M.F., Rott, R., Klenk, H.D. Virology (1990) [Pubmed]
  15. Long chain non-esterified fatty acid pattern in plasma of cystic fibrosis patients and their parents. Rogiers, V., Dab, I., Crokaert, R., Vis, H.L. Pediatr. Res. (1980) [Pubmed]
  16. Mapping the active site in vasoactive intestinal peptide to a core of four amino acids: neuroprotective drug design. Gozes, I., Perl, O., Giladi, E., Davidson, A., Ashur-Fabian, O., Rubinraut, S., Fridkin, M. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  17. Membrane fluidity changes accompanying phagocytosis in normal and in chronic granulomatous disease polymorphonuclear leukocytes. Ingraham, L.M., Boxer, L.A., Haak, R.A., Baehner, R.L. Blood (1981) [Pubmed]
  18. Differential fatty acid selection during biosynthetic S-acylation of a transmembrane protein (HEF) and other proteins in insect cells (Sf9) and in mammalian cells (CV1). Reverey, H., Veit, M., Ponimaskin, E., Schmidt, M.F. J. Biol. Chem. (1996) [Pubmed]
  19. Benzophenone-sensitized photooxidation of sarcoplasmic reticulum membranes: site-specific modification of the Ca(2+)-ATPase. Krainev, A.K., Viner, R.I., Bigelow, D.J. Free Radic. Biol. Med. (1997) [Pubmed]
  20. High-stearic and High-oleic cottonseed oils produced by hairpin RNA-mediated post-transcriptional gene silencing. Liu, Q., Singh, S.P., Green, A.G. Plant Physiol. (2002) [Pubmed]
  21. Depolymerization of microtubules increases the motional freedom of molecular probes in cellular plasma membranes. Aszalos, A., Yang, G.C., Gottesman, M.M. J. Cell Biol. (1985) [Pubmed]
  22. Interrelated lipid alterations and their influence on the proliferation and fusion of cultured myogenic cells. Horwitz, A.F., Wight, A., Ludwig, P., Cornell, R. J. Cell Biol. (1978) [Pubmed]
  23. Absence of unsaturated fatty acid synthesis in murine T lymphocytes. Buttke, T.M., Van Cleave, S., Steelman, L., McCubrey, J.A. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  24. Role of cholesterol in the capping of surface immunoglobulin receptors on murine lymphocytes. Hoover, R.L., Dawidowicz, E.A., Robinson, J.M., Karnovsky, M.J. J. Cell Biol. (1983) [Pubmed]
  25. Surface structure and properties of plant seed oil bodies. Tzen, J.T., Huang, A.H. J. Cell Biol. (1992) [Pubmed]
  26. 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]
  27. Bovine serum albumin. Study of the fatty acid and steroid binding sites using spin-labeled lipids. Morrisett, J.D., Pownall, H.J., Gotto, A.M. J. Biol. Chem. (1975) [Pubmed]
  28. Regulation of lysophospholipase activity of the 85-kDa phospholipase A2 and activation in mouse peritoneal macrophages. de Carvalho, M.G., Garritano, J., Leslie, C.C. J. Biol. Chem. (1995) [Pubmed]
  29. Identification of a mammalian long chain fatty acyl elongase regulated by sterol regulatory element-binding proteins. Moon, Y.A., Shah, N.A., Mohapatra, S., Warrington, J.A., Horton, J.D. J. Biol. Chem. (2001) [Pubmed]
  30. Ethanol tolerance in the yeast Saccharomyces cerevisiae is dependent on cellular oleic acid content. You, K.M., Rosenfield, C.L., Knipple, D.C. Appl. Environ. Microbiol. (2003) [Pubmed]
  31. Differential effects of interferon-gamma and -beta on fatty acid turnover, lipid bilayer fluidity and TNF-alpha release in murine macrophage J774.2 cells. Darmani, H., Harwood, J.L., Jackson, S.K. International journal of experimental pathology. (1995) [Pubmed]
  32. Disruption of the sterol 27-hydroxylase gene in mice results in hepatomegaly and hypertriglyceridemia. Reversal by cholic acid feeding. Repa, J.J., Lund, E.G., Horton, J.D., Leitersdorf, E., Russell, D.W., Dietschy, J.M., Turley, S.D. J. Biol. Chem. (2000) [Pubmed]
  33. Interactions of alpha-lactalbumin with fatty acids and spin label analogs. Cawthern, K.M., Narayan, M., Chaudhuri, D., Permyakov, E.A., Berliner, L.J. J. Biol. Chem. (1997) [Pubmed]
  34. Effects of diets containing high or low amounts of stearic acid on plasma lipoprotein fractions and fecal fatty acid excretion of men. Dougherty, R.M., Allman, M.A., Iacono, J.M. Am. J. Clin. Nutr. (1995) [Pubmed]
  35. Characterization and identification of an adrenal age-related nonpolar fluorescent substance. Cheng, B., Tserng, K.Y., Kowal, J., Buekers, K.S., Abraham, S., Gerhart, J.P. Endocrinology (1996) [Pubmed]
  36. Phase behavior of artificial stratum corneum lipids containing a synthetic pseudo-ceramide: a study of the function of cholesterol. Mizushima, H., Fukasawa, J., Suzuki, T. J. Lipid Res. (1996) [Pubmed]
  37. Fatty acid desaturation in lung: inhibition by unsaturated fatty acids. Balint, J.A., Kyriakides, E.C., Beeler, D.A. J. Lipid Res. (1980) [Pubmed]
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