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Chemical Compound Review

AC1NQXQS     (5Z,8Z,11Z,13E,15S)-15- hydroperoxyicosa-5...

Synonyms: CHEMBL1606580, BSPBio_001339, CHEBI:15628, HMDB04244, BML1-C06, ...
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Disease relevance of 15S-HpETE


High impact information on 15S-HpETE

  • These fatty acids depressed the expression of TNF mRNA in Mono Mac 6 cells stimulated with LPS; 15-HPETE was fivefold more active than 20:4n-6 and 15-HETE [1].
  • Lipoxin B (LXB) was prepared by incubation of (15S)-15-hydroperoxy-5,8,11-cis-13-trans-icosatetraenoic acid (15-HPETE) with human leukocytes [4].
  • Incubation of the 15-HETE precursor 15-HPETE with endothelial cells resulted in the formation of four distinct ultraviolet light-absorbing peaks [5].
  • Leukocyte preparations convert the hydroperoxy icosatetraenoic acids 5(S)-HPETE and 15(S)-HPETE to the unstable leukotriene epoxides LTA4 and 14,15-LTA4 [6].
  • TNF-alpha-induced increased expression of ICAM-1, E-selectin, and VCAM-1 mRNA was significantly depressed by 15-HPETE [7].

Biological context of 15S-HpETE


Anatomical context of 15S-HpETE


Associations of 15S-HpETE with other chemical compounds


Gene context of 15S-HpETE


Analytical, diagnostic and therapeutic context of 15S-HpETE

  • Aortic homogenates were incubated in the presence of [U-14C]arachidonic acid, [U-14C]arachidonic acid plus 15-lipoxygenase (soybean lipoxidase), or [U-14C]15-hydroxyeicosatetraenoic acid (15-HPETE) and analyzed by reverse phase high pressure liquid chromatography (RP-HPLC) [14].
  • Furthermore, careful application of this HPLC technique led to the isolation of two minor [1-14C]-labelled fractions which according to their spectral and chromatographic characteristics, were identical with 15(S)-hydroperoxy-5,8,11,13-eicosatetraenoic acid (15-HPETE) and 15(S)-hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE) [26].
  • The endoperoxide, PGH2 reduced perfusion pressure, this effect being inhibited by concurrent infusion of 15-HPETE [27].


  1. Altered responses of human macrophages to lipopolysaccharide by hydroperoxy eicosatetraenoic acid, hydroxy eicosatetraenoic acid, and arachidonic acid. Inhibition of tumor necrosis factor production. Ferrante, J.V., Huang, Z.H., Nandoskar, M., Hii, C.S., Robinson, B.S., Rathjen, D.A., Poulos, A., Morris, C.P., Ferrante, A. J. Clin. Invest. (1997) [Pubmed]
  2. Lipid hydroperoxides induce apoptosis in T cells displaying a HIV-associated glutathione peroxidase deficiency. Sandstrom, P.A., Tebbey, P.W., Van Cleave, S., Buttke, T.M. J. Biol. Chem. (1994) [Pubmed]
  3. Cytotoxicity of arachidonic acid and of its lipoxygenase metabolite 15-hydroperoxyeicosatetraenoic acid on human breast cancer MCF-7 cells in culture. Najid, A., Beneytout, J.L., Tixier, M. Cancer Lett. (1989) [Pubmed]
  4. On the stereochemistry and biosynthesis of lipoxin B. Serhan, C.N., Hamberg, M., Samuelsson, B., Morris, J., Wishka, D.G. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  5. Evidence for 15-HETE synthesis by human umbilical vein endothelial cells. Gorman, R.R., Oglesby, T.D., Bundy, G.L., Hopkins, N.K. Circulation (1985) [Pubmed]
  6. Evidence for a lipoxygenase mechanism in the biosynthesis of epoxide and dihydroxy leukotrienes from 15(S)-hydroperoxyicosatetraenoic acid by human platelets and porcine leukocytes. Maas, R.L., Brash, A.R. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  7. Inhibition of stimulus-induced endothelial cell intercellular adhesion molecule-1, E-selectin, and vascular cellular adhesion molecule-1 expression by arachidonic acid and its hydroxy and hydroperoxy derivatives. Huang, Z.H., Bates, E.J., Ferrante, J.V., Hii, C.S., Poulos, A., Robinson, B.S., Ferrante, A. Circ. Res. (1997) [Pubmed]
  8. Crystal structure of Escherichia coli thiol peroxidase in the oxidized state: insights into intramolecular disulfide formation and substrate binding in atypical 2-Cys peroxiredoxins. Choi, J., Choi, S., Choi, J., Cha, M.K., Kim, I.H., Shin, W. J. Biol. Chem. (2003) [Pubmed]
  9. The lipoxins. Stereochemical identification and determination of their biosynthesis. Fitzsimmons, B.J., Adams, J., Evans, J.F., Leblanc, Y., Rokach, J. J. Biol. Chem. (1985) [Pubmed]
  10. Novel role of lipoxygenases in the inflammatory response: promotion of TNF mRNA decay by 15-hydroperoxyeicosatetraenoic acid in a monocytic cell line. Ferrante, J.V., Ferrante, A. J. Immunol. (2005) [Pubmed]
  11. Lipoxygenase metabolites induced expression of adhesion molecules and transendothelial migration of monocyte-like HL-60 cells is linked to protein kinase C activation. Sultana, C., Shen, Y., Rattan, V., Kalra, V.K. J. Cell. Physiol. (1996) [Pubmed]
  12. Eicosanoid mediator expression in mononuclear and polymorphonuclear cells in normal subjects and patients with atopic asthma and cystic fibrosis. Kuitert, L.M., Newton, R., Barnes, N.C., Adcock, I.M., Barnes, P.J. Thorax (1996) [Pubmed]
  13. Effect of lipoxygenase metabolites of arachidonic acid on proliferation of human T cells and T cell subsets. Gualde, N., Atluru, D., Goodwin, J.S. J. Immunol. (1985) [Pubmed]
  14. Identification of the 11,14,15- and 11,12, 15-trihydroxyeicosatrienoic acids as endothelium-derived relaxing factors of rabbit aorta. Pfister, S.L., Spitzbarth, N., Nithipatikom, K., Edgemond, W.S., Falck, J.R., Campbell, W.B. J. Biol. Chem. (1998) [Pubmed]
  15. Induction of suppressor cells from peripheral blood T cells by 15-hydroperoxyeicosatetraenoic acid (15-HPETE). Gualde, N., Rigaud, M., Goodwin, J.S. J. Immunol. (1985) [Pubmed]
  16. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14, 15-leukotriene A4. Bryant, R.W., Schewe, T., Rapoport, S.M., Bailey, J.M. J. Biol. Chem. (1985) [Pubmed]
  17. Human thioredoxin reductase directly reduces lipid hydroperoxides by NADPH and selenocystine strongly stimulates the reaction via catalytically generated selenols. Björnstedt, M., Hamberg, M., Kumar, S., Xue, J., Holmgren, A. J. Biol. Chem. (1995) [Pubmed]
  18. Mechanism of hydroperoxide reduction by mangano-prostaglandin endoperoxide synthase. Landino, L.M., Marnett, L.J. Biochemistry (1996) [Pubmed]
  19. Hydroperoxide lyase in rabbit leukocytes: conversion of 15-hydroperoxyeicosatetraenoic acid to 15-keto-pentadeca-5,8,11,13-tetraenoic acid. Lam, B.K., Linh, Y.L., Ho, H.Y., Wong, P.Y. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  20. Differential effects of 15-HPETE on arachidonic acid metabolism in collagen-stimulated human platelets. Vedelago, H.R., Mahadevappa, V.G. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  21. The human sperm acrosome reaction does not depend on arachidonic acid metabolism via the cyclooxygenase and lipoxygenase pathways. Mack, S.R., Han, H.L., De Jonge, J., Anderson, R.A., Zaneveld, L.J. J. Androl. (1992) [Pubmed]
  22. Thioredoxin reductase regulates the induction of haem oxygenase-1 expression in aortic endothelial cells. Trigona, W.L., Mullarky, I.K., Cao, Y., Sordillo, L.M. Biochem. J. (2006) [Pubmed]
  23. Contribution of arachidonate metabolites to basal and thyrotropin releasing-hormone-stimulated release of prolactin from purified lactotrophs in primary culture. Junier, M.P., Israel, J.M., Dray, F., Vincent, J.D. Life Sci. (1990) [Pubmed]
  24. Immunoaffinity purification and characterization of thromboxane synthase from porcine lung. Shen, R.F., Tai, H.H. J. Biol. Chem. (1986) [Pubmed]
  25. Effects of 15-hydroperoxyeicosatetraenoic acid on human lymphocyte sheep erythrocyte rosette formation and response to concanavalin A associated with HLA system. Gualde, N., Rabinovitch, H., Fredon, M., Rigaud, M. Eur. J. Immunol. (1982) [Pubmed]
  26. Preparative HPLC purification of prostaglandin endoperoxides and isolation of novel cyclooxygenase-derived arachidonic acid metabolites. Hecker, M., Hatzelmann, A., Ullrich, V. Biochem. Pharmacol. (1987) [Pubmed]
  27. Investigation of the vascular actions of arachidonate lipoxygenase and cyclo-oxygenase products on the isolated perfused stomach of rat and rabbit. Salvati, P., Whittle, B.J. Prostaglandins (1981) [Pubmed]
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