oleic acids


Summary: A group of fatty acids that contain 18 carbon atoms and a double bond at the omega 9 carbon.

Top Publications

  1. Batchu S, Lee S, Qadhi R, Chaudhary K, El Sikhry H, Kodela R, et al. Cardioprotective effect of a dual acting epoxyeicosatrienoic acid analogue towards ischaemia reperfusion injury. Br J Pharmacol. 2011;162:897-907 pubmed publisher
    ..UA-8 provides significant cardioprotection against ischaemia reperfusion injury. The effects are attributed to EETs mimetic properties, which limits mitochondrial dysfunction via class-I PI3K signalling. ..
  2. Herrera S, Fernández O, Vera O, Cárdenas W, Ramirez O, Palacios R, et al. Phase I safety and immunogenicity trial of Plasmodium vivax CS derived long synthetic peptides adjuvanted with montanide ISA 720 or montanide ISA 51. Am J Trop Med Hyg. 2011;84:12-20 pubmed publisher
    ..Vaccines in Montanide ISA 51 showed a higher sporozoite protein recognition and interferon production. Results encourage further testing of the vaccine protective efficacy. ..
  3. Mossberg A, Hou Y, Svensson M, Holmqvist B, Svanborg C. HAMLET treatment delays bladder cancer development. J Urol. 2010;183:1590-7 pubmed publisher
    ..Results show that HAMLET is active as a tumoricidal agent and suggest that topical HAMLET administration may delay bladder cancer development. ..
  4. Gaetani S, Fu J, Cassano T, Dipasquale P, Romano A, Righetti L, et al. The fat-induced satiety factor oleoylethanolamide suppresses feeding through central release of oxytocin. J Neurosci. 2010;30:8096-101 pubmed publisher
    ..The results suggest that OEA suppresses feeding by activating central oxytocin transmission. ..
  5. Mossberg A, Hun Mok K, Morozova Roche L, Svanborg C. Structure and function of human ?-lactalbumin made lethal to tumor cells (HAMLET)-type complexes. FEBS J. 2010;277:4614-25 pubmed publisher
  6. Jang S, Lillehoj H, Lee S, Lee K, Lillehoj E, Bertrand F, et al. Mucosal immunity against Eimeria acervulina infection in broiler chickens following oral immunization with profilin in Montanide™ adjuvants. Exp Parasitol. 2011;129:36-41 pubmed publisher
    ..acervulina infection...
  7. Marcilla Etxenike A, Martin M, Noguera Salva M, Garcia Verdugo J, Soriano Navarro M, Dey I, et al. 2-Hydroxyoleic acid induces ER stress and autophagy in various human glioma cell lines. PLoS ONE. 2012;7:e48235 pubmed publisher
  8. Morera Y, Bequet Romero M, Ayala M, Velazco J, Pérez P, Alba J, et al. Immunogenicity and some safety features of a VEGF-based cancer therapeutic vaccine in rats, rabbits and non-human primates. Vaccine. 2010;28:3453-61 pubmed publisher
    ..Immunization with CIGB-247 had no effect on normal behavior, hematology, blood biochemistry and histology of critical organs, in the tested animals. Skin deep wound healing was not affected in vaccinated rats and monkeys...
  9. Wang L, Han X, Mehren J, Hiroi M, Billeter J, Miyamoto T, et al. Hierarchical chemosensory regulation of male-male social interactions in Drosophila. Nat Neurosci. 2011;14:757-62 pubmed publisher
    ..Thus, male social behaviors are controlled by gustatory pheromones that promote aggression and suppress courtship, and whose influences are dominant to olfactory pheromones that enhance these behaviors. ..

More Information


  1. Chertemps T, François A, Durand N, Rosell G, Dekker T, Lucas P, et al. A carboxylesterase, Esterase-6, modulates sensory physiological and behavioral response dynamics to pheromone in Drosophila. BMC Biol. 2012;10:56 pubmed publisher
    ..As Est-6 is also known to hydrolyze cVA in vitro and is expressed in the main olfactory organ, the antenna, we tested here its role in olfaction as a putative odorant-degrading enzyme...
  2. Yoshimatsu R, Yamagami T, Tanaka O, Miura H, Okuda K, Hashiba M, et al. Development of thrombus in a systemic vein after balloon-occluded retrograde transvenous obliteration of gastric varices. Korean J Radiol. 2012;13:324-31 pubmed publisher
    ..Physicians should be aware of the possibility of pulmonary embolism due to iliocaval thrombosis. ..
  3. Jang S, Lillehoj H, Lee S, Lee K, Lillehoj E, Bertrand F, et al. Montanide™ ISA 71 VG adjuvant enhances antibody and cell-mediated immune responses to profilin subunit antigen vaccination and promotes protection against Eimeria acervulina and Eimeria tenella. Exp Parasitol. 2011;127:178-83 pubmed publisher
    ..These results demonstrate that the recombinant profilin subunit vaccine, when given in combination with Montanide™ ISA 71 VG, augments protective immunity against E. acervulina and E. tenella. ..
  4. Ozaki M, Kurita M, Kaji N, Fujino T, Narushima M, Takushima A, et al. Efficacy and evaluation of safety of sclerosants for intramuscular venous malformations: clinical and experimental studies. Scand J Plast Reconstr Surg Hand Surg. 2010;44:75-87 pubmed publisher
    ..In the experimental study, ethanol had a more detrimental effect on muscles than the other agents. We consider that ethanolamine oleate is the most suitable sclerosant for the treatment of intramuscular venous malformations...
  5. Ren J, Yang L, Xu H, Zhang Y, Wan M, Liu G, et al. CpG oligodeoxynucleotide and montanide ISA 206 adjuvant combination augments the immune responses of a recombinant FMDV vaccine in cattle. Vaccine. 2011;29:7960-5 pubmed publisher
    ..These findings suggest that CpG ODN RW03 could be used with Montanide ISA 206 as a potent adjuvant for recombinant FMDV in cattle. ..
  6. Martin M, Barcelo Coblijn G, de Almeida R, Noguera Salva M, Terés S, Higuera M, et al. The role of membrane fatty acid remodeling in the antitumor mechanism of action of 2-hydroxyoleic acid. Biochim Biophys Acta. 2013;1828:1405-13 pubmed publisher
  7. Ronderos D, Smith D. Activation of the T1 neuronal circuit is necessary and sufficient to induce sexually dimorphic mating behavior in Drosophila melanogaster. J Neurosci. 2010;30:2595-9 pubmed publisher
    ..These findings demonstrate that the T1/Or67d circuit is necessary and sufficient to mediate sexually dimorphic courtship behaviors. ..
  8. Mercer N, Ramakrishnan B, Boeggeman E, Qasba P. Applications of site-specific labeling to study HAMLET, a tumoricidal complex of ?-lactalbumin and oleic acid. PLoS ONE. 2011;6:e26093 pubmed publisher
    ..The HAMLET conjugated with a single biotin molecule will be a useful tool to identify the cellular components that are involved with it in the tumoricidal activity. ..
  9. Barcelo Coblijn G, Martin M, de Almeida R, Noguera Salva M, Marcilla Etxenike A, Guardiola Serrano F, et al. Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy. Proc Natl Acad Sci U S A. 2011;108:19569-74 pubmed publisher
    ..Finally, the specific activation of SMS explains the ability of this compound to trigger cell cycle arrest, cell differentiation, and autophagy or apoptosis in cancer cells. ..
  10. Baumann A, Gjerde A, Ying M, Svanborg C, Holmsen H, Glomm W, et al. HAMLET forms annular oligomers when deposited with phospholipid monolayers. J Mol Biol. 2012;418:90-102 pubmed publisher
  11. Trulsson M, Yu H, Gisselsson L, Chao Y, Urbano A, Aits S, et al. HAMLET binding to ?-actinin facilitates tumor cell detachment. PLoS ONE. 2011;6:e17179 pubmed publisher
    ..As ?-actinins also associate with signaling molecules, cytoplasmic domains of transmembrane receptors and ion channels, additional ?-actinin-dependent mechanisms are discussed. ..
  12. Serrano A, Pavon F, Tovar S, Casanueva F, Señarís R, Dieguez C, et al. Oleoylethanolamide: effects on hypothalamic transmitters and gut peptides regulating food intake. Neuropharmacology. 2011;60:593-601 pubmed publisher
  13. Terés S, Llado V, Higuera M, Barcelo Coblijn G, Martin M, Noguera Salva M, et al. 2-Hydroxyoleate, a nontoxic membrane binding anticancer drug, induces glioma cell differentiation and autophagy. Proc Natl Acad Sci U S A. 2012;109:8489-94 pubmed publisher
    ..Given its high efficacy, low toxicity, ease of oral administration, and good distribution to the brain, 2OHOA constitutes a new and potentially valuable therapeutic tool for glioma patients. ..
  14. Jang S, Lillehoj H, Lee S, Lee K, Park M, Bauchan G, et al. Immunoenhancing effects of Montanide ISA oil-based adjuvants on recombinant coccidia antigen vaccination against Eimeria acervulina infection. Vet Parasitol. 2010;172:221-8 pubmed publisher
    ..These results demonstrate that vaccination with the E. acervulina profilin subunit vaccine in combination with Montanide adjuvants enhances protective immunity against avian coccidiosis. ..
  15. Hansen H. Palmitoylethanolamide and other anandamide congeners. Proposed role in the diseased brain. Exp Neurol. 2010;224:48-55 pubmed publisher
  16. Marks L, Clementi E, Hakansson A. The human milk protein-lipid complex HAMLET sensitizes bacterial pathogens to traditional antimicrobial agents. PLoS ONE. 2012;7:e43514 pubmed publisher
    ..Combined these results suggest the presence of a conserved HAMLET-activated pathway that circumvents antibiotic resistance in bacteria. The ability to activate this pathway may extend the lifetime of the current treatment arsenal. ..
  17. Hakansson A, Roche Hakansson H, Mossberg A, Svanborg C. Apoptosis-like death in bacteria induced by HAMLET, a human milk lipid-protein complex. PLoS ONE. 2011;6:e17717 pubmed publisher
    ..Identifying the mechanisms of bacterial cell death has the potential to reveal novel targets for future antimicrobial therapy and to further our understanding of core activation mechanisms of cell death in eukaryote cells. ..
  18. Storm P, Aits S, Puthia M, Urbano A, Northen T, Powers S, et al. Conserved features of cancer cells define their sensitivity to HAMLET-induced death; c-Myc and glycolysis. Oncogene. 2011;30:4765-79 pubmed publisher
    ..The results identify HAMLET as a novel anti-cancer agent that kills tumor cells by exploiting unifying features of cancer cells such as oncogene addiction or the Warburg effect. ..
  19. Katti S, Lokhande N, Gonzalez D, Cassill A, Renthal R. Quantitative analysis of pheromone-binding protein specificity. Insect Mol Biol. 2013;22:31-40 pubmed publisher
    ..The results indicate that the ligand-binding cavity of LUSH can accommodate a variety ligands with strong binding interactions. Implications of this for the Laughlin, Ha, Jones and Smith model of pheromone reception are discussed...
  20. Graham B, McElrath M, Keefer M, Rybczyk K, Berger D, Weinhold K, et al. Immunization with cocktail of HIV-derived peptides in montanide ISA-51 is immunogenic, but causes sterile abscesses and unacceptable reactogenicity. PLoS ONE. 2010;5:e11995 pubmed publisher
    ..If potent adjuvants are necessary for subunit vaccines to induce broad and durable immune responses, careful, incremental clinical evaluation is warranted to minimize the risk of adverse events. ClinicalTrials.gov NCT00000886. ..
  21. Lekogo B, Coroller L, Mathot A, Mafart P, Leguerinel I. Modelling the influence of palmitic, palmitoleic, stearic and oleic acids on apparent heat resistance of spores of Bacillus cereus NTCC 11145 and Clostridium sporogenes Pasteur 79.3. Int J Food Microbiol. 2010;141:242-7 pubmed publisher
    ..3. Four free fatty acids were studied: palmitic, palmitoleic, stearic and oleic acids. During thermal treatments, the impact of these FFA in heating media was generally low, but the presence of ..
  22. Martínez J, Gutierrez A, CASAS J, Llado V, López Bellan A, Besalduch J, et al. The repression of E2F-1 is critical for the activity of Minerval against cancer. J Pharmacol Exp Ther. 2005;315:466-74 pubmed
    ..Interestingly, whereas the changes induced by OA were only modest, they may reflect the beneficial effects of high olive oil intake against cancer. ..
  23. Roestenberg M, Remarque E, de Jonge E, Hermsen R, Blythman H, Leroy O, et al. Safety and immunogenicity of a recombinant Plasmodium falciparum AMA1 malaria vaccine adjuvanted with Alhydrogel, Montanide ISA 720 or AS02. PLoS ONE. 2008;3:e3960 pubmed publisher
    ..Plasmodium falciparum Apical Membrane Antigen 1 (PfAMA1) is a candidate vaccine antigen expressed by merozoites and sporozoites. It plays a key role in red blood cell and hepatocyte invasion that can be blocked by antibodies...
  24. Pettersson Kastberg J, Aits S, Gustafsson L, Mossberg A, Storm P, Trulsson M, et al. Can misfolded proteins be beneficial? The HAMLET case. Ann Med. 2009;41:162-76 pubmed publisher
  25. Mok K, Pettersson J, Orrenius S, Svanborg C. HAMLET, protein folding, and tumor cell death. Biochem Biophys Res Commun. 2007;354:1-7 pubmed
  26. Llado V, Gutierrez A, Martínez J, CASAS J, Terés S, Higuera M, et al. Minerval induces apoptosis in Jurkat and other cancer cells. J Cell Mol Med. 2010;14:659-70 pubmed publisher
    ..This is the first report on the pro-apoptotic activity of Minerval, and in part explains the effectiveness of this non-toxic anticancer drug and its wide spectrum against different types of cancer. ..
  27. Koethe D, Giuffrida A, Schreiber D, Hellmich M, Schultze Lutter F, Ruhrmann S, et al. Anandamide elevation in cerebrospinal fluid in initial prodromal states of psychosis. Br J Psychiatry. 2009;194:371-2 pubmed publisher
    ..Patients with lower levels showed a higher risk for transiting to psychosis earlier. This anandamidergic up-regulation in the initial prodromal course may suggest a protective role of the endocannabinoid system in early schizophrenia. ..
  28. Ropero A, Juan Pico P, Rafacho A, Fuentes E, Bermúdez Silva F, Roche E, et al. Rapid non-genomic regulation of Ca2+ signals and insulin secretion by PPAR alpha ligands in mouse pancreatic islets of Langerhans. J Endocrinol. 2009;200:127-38 pubmed publisher
    ..We conclude that PPAR alpha agonists produce a decrease in glucose-induced [Ca2+]i signals and insulin secretion in beta-cells through a rapid, non-genomic mechanism. ..
  29. Aucouturier J, Ascarateil S, Dupuis L. The use of oil adjuvants in therapeutic vaccines. Vaccine. 2006;24 Suppl 2:S2-44-5 pubmed
  30. Tolin S, De Franceschi G, Spolaore B, Frare E, Canton M, Polverino De Laureto P, et al. The oleic acid complexes of proteolytic fragments of alpha-lactalbumin display apoptotic activity. FEBS J. 2010;277:163-73 pubmed publisher
    ..We conclude that the entire sequence of the protein is not required to form an apoptotic OA complex, and we suggest that the apoptotic activity of a protein-OA complex does not imply specific binding of the protein. ..
  31. Ejima A, Smith B, Lucas C, Van der Goes van Naters W, Miller C, Carlson J, et al. Generalization of courtship learning in Drosophila is mediated by cis-vaccenyl acetate. Curr Biol. 2007;17:599-605 pubmed
    ..These findings suggest that transfer of cVA to females during mating may be part of the male's strategy to suppress reproduction by competing males. ..
  32. Yamagami T, Kato T, Hirota T, Yoshimatsu R, Matsumoto T, Nishimura T. Infusion of 50% glucose solution before injection of ethanolamine oleate during balloon-occluded retrograde transvenous obliteration. Australas Radiol. 2007;51:334-8 pubmed
    ..In three patients, embolization of collateral vessels with coils was unnecessary. There were no complications. In conclusion, retrograde infusion of 50% glucose solution assists in effectively carrying out BRTO. ..
  33. Suardiaz M, Estivill Torrus G, Goicoechea C, Bilbao A, Rodriguez de Fonseca F. Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain. Pain. 2007;133:99-110 pubmed
    ..This study represents a novel approach to the examination of the effectiveness of OEA in nociceptive responses and provides a framework for understanding its biological functions and endogenous targets in visceral and inflammatory pain. ..
  34. Martínez de Ubago M, García Oya I, Pérez Pérez A, Canfrán Duque A, Quintana Portillo R, Rodriguez de Fonseca F, et al. Oleoylethanolamide, a natural ligand for PPAR-alpha, inhibits insulin receptor signalling in HTC rat hepatoma cells. Biochim Biophys Acta. 2009;1791:740-5 pubmed publisher
    ..In summary, OEA inhibits insulin metabolic and mitogenic signalling by activation of JNK and p38 MAPK via PPAR-alpha. ..
  35. Mossberg A, Wullt B, Gustafsson L, Mansson W, Ljunggren E, Svanborg C. Bladder cancers respond to intravesical instillation of HAMLET (human alpha-lactalbumin made lethal to tumor cells). Int J Cancer. 2007;121:1352-9 pubmed
    ..The results suggest that HAMLET exerts a direct and selective effect on bladder cancer tissue in vivo and that local HAMLET administration might be of value in the future treatment of bladder cancers. ..
  36. Wilhelm K, Darinskas A, Noppe W, Duchardt E, Mok K, Vukojevic V, et al. Protein oligomerization induced by oleic acid at the solid-liquid interface--equine lysozyme cytotoxic complexes. FEBS J. 2009;276:3975-89 pubmed publisher
    ..Each lysozyme molecule is able to bind 11-48 oleic acids in various preparations...
  37. Druilhe P, Spertini F, Soesoe D, Corradin G, Mejia P, Singh S, et al. A malaria vaccine that elicits in humans antibodies able to kill Plasmodium falciparum. PLoS Med. 2005;2:e344 pubmed
  38. Langermans J, Hensmann M, van Gijlswiik M, Zhang D, Pan W, Giersing B, et al. Preclinical evaluation of a chimeric malaria vaccine candidate in Montanide ISA 720: immunogenicity and safety in rhesus macaques. Hum Vaccin. 2006;2:222-6 pubmed
    ..9/ISA 720 formulation. ..
  39. Aits S, Gustafsson L, Hallgren O, Brest P, Gustafsson M, Trulsson M, et al. HAMLET (human alpha-lactalbumin made lethal to tumor cells) triggers autophagic tumor cell death. Int J Cancer. 2009;124:1008-19 pubmed publisher
    ..The results show that HAMLET triggers macroautophagy in tumor cells and suggest that macroautophagy contributes to HAMLET-induced tumor cell death. ..
  40. Cano C, Pavón J, Serrano A, Goya P, Paez J, de Fonseca F, et al. Novel sulfamide analogs of oleoylethanolamide showing in vivo satiety inducing actions and PPARalpha activation. J Med Chem. 2007;50:389-93 pubmed
    ..Among the active compounds N-octadecyl-N'-propylsulfamide (7) has been identified as a potent hypolipidemic compound, a potent feeding suppressant, and a concentration-dependent activator of PPARalpha. ..
  41. Hoi P, Hiley C. Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor. Br J Pharmacol. 2006;147:560-8 pubmed
    ..Oleamide may share a receptor (sensitive to rimonabant and O-1918, and coupled to KC) and Gi/o) with anandamide in this vessel. This might be distinct from both of the known cannabinoid receptors and the novel abnormal-cannabidiol site. ..
  42. Salas A, Remesar X, Esteve M. Oleoyl-estrone treatment activates apoptotic mechanisms in white adipose tissue. Life Sci. 2007;80:293-8 pubmed
    ..No effect was detected in subcutaneous or retroperitoneal adipose tissue. The increased expression of apoptotic factors suggests that this pathway could be activated by OE treatment. ..
  43. Tholstrup T, Raff M, Basu S, Nonboe P, Sejrsen K, Straarup E. Effects of butter high in ruminant trans and monounsaturated fatty acids on lipoproteins, incorporation of fatty acids into lipid classes, plasma C-reactive protein, oxidative stress, hemostatic variables, and insulin in healthy young men. Am J Clin Nutr. 2006;83:237-43 pubmed
    ..It may be that the differences were due to the greater content of monounsaturated FAs and the lesser content of saturated FAs in the butter rich in ruminant trans FAs, rather than to the content of vaccenic acid per se. ..
  44. Schwartz G, Fu J, Astarita G, Li X, Gaetani S, Campolongo P, et al. The lipid messenger OEA links dietary fat intake to satiety. Cell Metab. 2008;8:281-288 pubmed publisher
    ..The results suggest that activation of small-intestinal OEA mobilization, enabled by CD36-mediated uptake of dietary oleic acid, serves as a molecular sensor linking fat ingestion to satiety. ..
  45. Yang Y, Chen M, Georgeson K, Harmon C. Mechanism of oleoylethanolamide on fatty acid uptake in small intestine after food intake and body weight reduction. Am J Physiol Regul Integr Comp Physiol. 2007;292:R235-41 pubmed
    ..This study may have important implications in understanding the mechanism of OEA in the regulation of fatty acid absorption in human physiological and pathophysiological conditions. ..
  46. Van der Goes van Naters W, Carlson J. Receptors and neurons for fly odors in Drosophila. Curr Biol. 2007;17:606-12 pubmed
    ..We propose a model describing how these receptors might be used by a male to distinguish suitable from unsuitable mating partners through a simple logic. ..
  47. Diefenbach C, Gnjatic S, Sabbatini P, Aghajanian C, Hensley M, Spriggs D, et al. Safety and immunogenicity study of NY-ESO-1b peptide and montanide ISA-51 vaccination of patients with epithelial ovarian cancer in high-risk first remission. Clin Cancer Res. 2008;14:2740-8 pubmed publisher
    ..Additional study is warranted. ..
  48. Fu J, Astarita G, Gaetani S, Kim J, Cravatt B, Mackie K, et al. Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine. J Biol Chem. 2007;282:1518-28 pubmed
    ..Collectively, these results indicate that nutrient availability controls OEA mobilization in the mucosa of the proximal intestine through a concerted regulation of OEA biosynthesis and degradation. ..
  49. Langermans J, Schmidt A, Vervenne R, Birkett A, Calvo Calle J, Hensmann M, et al. Effect of adjuvant on reactogenicity and long-term immunogenicity of the malaria Vaccine ICC-1132 in macaques. Vaccine. 2005;23:4935-43 pubmed
    ..Such measures also reduced peak titres and longevity of antibodies against CS, demonstrating the delicate balance between immunogenicity and reactogenicity of new vaccine formulations...
  50. Schlief M, Wilson R. Olfactory processing and behavior downstream from highly selective receptor neurons. Nat Neurosci. 2007;10:623-30 pubmed
  51. Bu D, Wang J, Dhiman T, Liu S. Effectiveness of oils rich in linoleic and linolenic acids to enhance conjugated linoleic acid in milk from dairy cows. J Dairy Sci. 2007;90:998-1007 pubmed
    ..Increasing the proportion of healthy fatty acids (VA and CLA) by feeding soybean or flaxseed oil would result in milk with higher nutritive and therapeutic value. ..
  52. Akahoshi T, Hashizume M, Tomikawa M, Kawanaka H, Yamaguchi S, Konishi K, et al. Long-term results of balloon-occluded retrograde transvenous obliteration for gastric variceal bleeding and risky gastric varices: a 10-year experience. J Gastroenterol Hepatol. 2008;23:1702-9 pubmed publisher
    ..We believe that B-RTO can become a first-choice radical treatment following hemostasis for gastric variceal bleeding and prophylactic treatment for risky GVx. ..
  53. Wang Y, Lu J, Ruth M, Goruk S, Reaney M, Glimm D, et al. Trans-11 vaccenic acid dietary supplementation induces hypolipidemic effects in JCR:LA-cp rats. J Nutr. 2008;138:2117-22 pubmed publisher
    ..In contrast, dietary VA had substantial hypo-triglyceridemic effects, suggesting a new bioactivity of this fatty acid that is typically found in ruminant-derived food products...