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Chemical Compound Review

Linoleate     (9Z,12Z)-octadeca-9,12-dienoic acid

Synonyms: Linolate, Linoleic, Leinoleic acid, Telfairic acid, Emersol 310, ...
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Disease relevance of Linoleate

  • We tested the hypothesis that the mechanism of melatonin's anticancer action in vivo involves the inhibition of tumor LA uptake and metabolism to 13-HODE in hepatoma 7288CTC [1].
  • In MDA-MB-231 cells, DADS antagonized the effect of linoleic acid (LA), a potent breast cancer cell stimulator (at DADS = 1.8 microM and LA > or = 6.5x10(2) microM concentration), and synergized the effect of eicosapentaenoic acid (EPA), a potent breast cancer cell suppressor (at DADS >3 x 10(-3) microM and EPA > 6.3 x 10(-1) microM concentration) [2].
  • A decreased percentage of linoleic acid (LA) in triglycerides, of arachidonic acid (AA) in PC and of eicosapentaenoic acid (EPA) in triglycerides, FFA, PC and PE could be found in the kidneys of SHR at 8 weeks of age, i.e. during the development of hypertension [3].

High impact information on Linoleate

  • Perfusion of tissue-isolated tumors in situ with melatonin (1 nM) rapidly and reversibly inhibited the uptake of plasma fatty acids (FAs), including LA, and its metabolism to 13-HODE [1].
  • The inhibition of these signal transduction events by melatonin culminates in the suppression of LA uptake, LA metabolism to the mitogenic signaling molecule 13-HODE, and cancer growth [1].
  • Growth of a yeast fox2sps19Delta mutant in which Fox2p was exchanged with rat peroxisomal multifunctional enzyme type 1 on trans-9,trans-12 linolelaidic acid medium gave credence to this theory [4].
  • Val-349 and Ser-530, recently identified as important determinants for efficient oxygenation of DHLA by PGHS-1, play similar roles in the oxygenation of EPA and LA [5].
  • Both EPA and LA bind in the active site with orientations similar to those seen previously with AA and dihomo-gamma-linolenic acid (DHLA) [5].

Chemical compound and disease context of Linoleate

  • The growth of rat hepatoma 7288CTC in vivo is stimulated by the uptake of linoleic acid (LA) and its metabolism to 13-hydroxyoctadecadienoic acid (13-HODE), an important mitogenic signaling molecule within this tumor [1].
  • Remarkably, omega-6 PUFAs linoleic acid (LA) and arachidonic acid (ARA), suppressors of both hepatic and adipocytic FAS-dependent lipogenesis, had no significant inhibitory effects on the activity of tumor-associated FAS in SK-Br3 breast cancer cells [6].
  • In support of this hypothesis, light during darkness suppresses nocturnal melatonin production and stimulates the LA metabolism and growth of rat hepatoma and human breast cancer xenografts [7].

Biological context of Linoleate


Anatomical context of Linoleate

  • The effects of preformed dietary arachidonic acid (AA, 20:4n-6) on murine phospholipid fatty acid composition in tissues capable (liver) and incapable (peritoneal exudate cells, PEC) of desaturating and elongating linoleic acid (LA, 18:2n-6) to AA were investigated [12].
  • OA, AA or LA did not change, but ALA enhanced tight junction permeability [13].
  • Lesser amounts of 9,12-octadecadienoic acid in less-pigmented cell walls may have been caused by the growth of the fungus under environmental stress conditions [14].
  • The effect of 13-hydroperoxyoctadecadienoic acid (13-HPODE), a hydroperoxy adduct of linoleic acid (LA), on the activities of prostaglandin (PG) synthesizing and catabolizing enzymes in rabbit gastric antral mucosa was examined [15].
  • The content of arachidonic and docosahexaenoic acid, the main products of the conversion of LA and ALA respectively, decreased, LA content increased and a decrease in the unsaturation index was observed in liver microsomes of B6-deficient rats [16].

Associations of Linoleate with other chemical compounds


Gene context of Linoleate


Analytical, diagnostic and therapeutic context of Linoleate

  • A dietary intervention study with healthy human volunteers that incorporated alpha-LA-rich vegetable oil (flaxseed oil), against a background diet low in LA, allowed us to examine these relationships [25].
  • We tested the ability of constant light exposure to suppress MLT production in female nude rats and stimulate the growth of tissue-isolated MCF-7 human breast cancer xenografts via increased tumor linoleic acid (LA) metabolism [26].
  • Generally, our data showed a marked immunomodulatory effect of 18-3 (n-3) alpha-linoleic acid on the exhaustive exercise-related immunosuppression, as compared to the effects of other selected PUFA [27].
  • It was found that the developed HPLC analysis was able to adequately separate the geometric isomers, linoleic acid (18:2 delta 9c, 12c) from linolelaidic acid (18:2 delta 9t, 12t) [28].


  1. Melatonin inhibition of cancer growth in vivo involves suppression of tumor fatty acid metabolism via melatonin receptor-mediated signal transduction events. Blask, D.E., Sauer, L.A., Dauchy, R.T., Holowachuk, E.W., Ruhoff, M.S., Kopff, H.S. Cancer Res. (1999) [Pubmed]
  2. Growth inhibitory effects of diallyl disulfide on human breast cancer cell lines. Nakagawa, H., Tsuta, K., Kiuchi, K., Senzaki, H., Tanaka, K., Hioki, K., Tsubura, A. Carcinogenesis (2001) [Pubmed]
  3. Age-dependent alterations of linoleic, arachidonic and eicosapentaenoic acids in renal cortex and medulla of spontaneously hypertensive rats. Singer, P., Wirth, M., Gerike, U., Gödicke, W., Moritz, V. Prostaglandins (1984) [Pubmed]
  4. Peroxisomal degradation of trans-unsaturated fatty acids in the yeast Saccharomyces cerevisiae. Gurvitz, A., Hamilton, B., Ruis, H., Hartig, A. J. Biol. Chem. (2001) [Pubmed]
  5. Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1. Malkowski, M.G., Thuresson, E.D., Lakkides, K.M., Rieke, C.J., Micielli, R., Smith, W.L., Garavito, R.M. J. Biol. Chem. (2001) [Pubmed]
  6. Overexpression and hyperactivity of breast cancer-associated fatty acid synthase (oncogenic antigen-519) is insensitive to normal arachidonic fatty acid-induced suppression in lipogenic tissues but it is selectively inhibited by tumoricidal alpha-linolenic and gamma-linolenic fatty acids: a novel mechanism by which dietary fat can alter mammary tumorigenesis. Menendez, J.A., Ropero, S., Mehmi, I., Atlas, E., Colomer, R., Lupu, R. Int. J. Oncol. (2004) [Pubmed]
  7. Putting cancer to sleep at night: the neuroendocrine/circadian melatonin signal. Blask, D.E., Dauchy, R.T., Sauer, L.A. Endocrine (2005) [Pubmed]
  8. Eicosapentaenoic acid suppresses cell proliferation in MCF-7 human breast cancer xenografts in nude rats via a pertussis toxin-sensitive signal transduction pathway. Sauer, L.A., Dauchy, R.T., Blask, D.E., Krause, J.A., Davidson, L.K., Dauchy, E.M. J. Nutr. (2005) [Pubmed]
  9. Effects of fatty acids, nucleotides and reactive oxygen species on durum wheat mitochondria. Pastore, D., Fratianni, A., Di Pede, S., Passarella, S. FEBS Lett. (2000) [Pubmed]
  10. Activation of protein kinase C by cis- and trans-octadecadienoic acids in intact human platelets and its potentiation by diacylglycerol. Seifert, R., Schächtele, C., Schultz, G. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  11. Autoxidation of fatty acid monolayers adsorbed on silica gel: II. Rates and products. Wu, G.S., Stein, R.A., Mead, J.F. Lipids (1977) [Pubmed]
  12. Dietary arachidonic and linoleic acids: comparative effects on tissue lipids. Whelan, J., Broughton, K.S., Surette, M.E., Kinsella, J.E. Lipids (1992) [Pubmed]
  13. Effect of eicosapentaenoic acid (EPA) on tight junction permeability in intestinal monolayer cells. Usami, M., Muraki, K., Iwamoto, M., Ohata, A., Matsushita, E., Miki, A. Clinical nutrition (Edinburgh, Scotland) (2001) [Pubmed]
  14. Comparative chemical characterization of pigmented and less pigmented cell walls of Alternaria tenuissima. Kishore, K.H., Kanjilal, S., Misra, S., Reddy, C.R., Murty, U.S. Curr. Microbiol. (2005) [Pubmed]
  15. Inhibition of 15-hydroxy prostaglandin dehydrogenase activity in rabbit gastric antral mucosa by 13-hydroperoxyoctadecadienoic acid. Sakuma, S., Fujimoto, Y., Miyata, Y., Yamane, K., Nishida, H., Fujita, T. Prostaglandins Leukot. Essent. Fatty Acids (1994) [Pubmed]
  16. Dual influence of aging and vitamin B6 deficiency on delta-6-desaturation of essential fatty acids in rat liver microsomes. Bordoni, A., Hrelia, S., Lorenzini, A., Bergami, R., Cabrini, L., Biagi, P.L., Tolomelli, B. Prostaglandins Leukot. Essent. Fatty Acids (1998) [Pubmed]
  17. Polymorphism of linoleic acid (cis-9, cis-12-octadecadienoic acid) and alpha-linolenic acid (cis-9, cis-12, cis-15-octadecatrienoic acid). Ueno, S., Miyazaki, A., Yano, J., Furukawa, Y., Suzuki, M., Sato, K. Chem. Phys. Lipids (2000) [Pubmed]
  18. Docosahexaenoic acid induces apoptosis in the human PaCa-44 pancreatic cancer cell line by active Reduced glutathione extrusion and lipid peroxidation. Merendino, N., Loppi, B., D'Aquino, M., Molinari, R., Pessina, G., Romano, C., Velotti, F. Nutrition and cancer. (2005) [Pubmed]
  19. Similar effects of diets high in oleic or linoleic acids on coagulation and fibrinolytic factors in healthy humans. Turpeinen, A.M., Mutanen, M. Nutrition, metabolism, and cardiovascular diseases : NMCD. (1999) [Pubmed]
  20. Effect of omega-3 fatty acid (docosahexanoic acid) on BRCA1 gene expression and growth in MCF-7 cell line. Kachhap, S.K., Dange, P.P., Santani, R.H., Sawant, S.S., Ghosh, S.N. Cancer Biother. Radiopharm. (2001) [Pubmed]
  21. 13-hydroxy- and 13-oxooctadecadienoic acids: novel substrates for human UDP-glucuronosyltransferases. Jude, A.R., Little, J.M., Bull, A.W., Podgorski, I., Radominska-Pandya, A. Drug Metab. Dispos. (2001) [Pubmed]
  22. Protection of lipids from oxidation by epicatechin, trans-resveratrol, and gallic and caffeic acids in intestinal model systems. Kerem, Z., Chetrit, D., Shoseyov, O., Regev-Shoshani, G. J. Agric. Food Chem. (2006) [Pubmed]
  23. Linoleic and linolelaidic acids differentially influence proliferation and apoptosis of MOLT-4 leukaemia cells. Phoon, M.C., Desbordes, C., Howe, J., Chow, V.T. Cell Biol. Int. (2001) [Pubmed]
  24. Light during darkness, melatonin suppression and cancer progression. Blask, D.E., Dauchy, R.T., Sauer, L.A., Krause, J.A., Brainard, G.C. Neuro Endocrinol. Lett. (2002) [Pubmed]
  25. Differences exist in the relationships between dietary linoleic and alpha-linolenic acids and their respective long-chain metabolites. Mantzioris, E., James, M.J., Gibson, R.A., Cleland, L.G. Am. J. Clin. Nutr. (1995) [Pubmed]
  26. Growth and fatty acid metabolism of human breast cancer (MCF-7) xenografts in nude rats: impact of constant light-induced nocturnal melatonin suppression. Blask, D.E., Dauchy, R.T., Sauer, L.A., Krause, J.A., Brainard, G.C. Breast Cancer Res. Treat. (2003) [Pubmed]
  27. Modulation of exercise-induced immunosuppression by dietary polyunsaturated fatty acids in mice. Benquet, C., Krzystyniak, K., Savard, R., Guertin, F., Oth, D., Fournier, M. Journal of toxicology and environmental health. (1994) [Pubmed]
  28. HPLC analysis of underivatized fatty acids in margarines. Bailie, A.G., Wilson, T.D., O'Brien, R.K., Beebe, J.M., Stuart, J.D., McCosh-Lilie, E., Hill, D.W. Journal of chromatographic science. (1982) [Pubmed]
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