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Chemical Compound Review

AC1O5S0M     (5Z,8Z,10E,12E)-13-[(2R,3R)- 3-pentyloxiran...

Synonyms: 81918-96-9, 14,15-Leukotriene A4, 14,15-Oxido-5,8,10,12-eicosatetraenoic acid
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High impact information on 14,15-Leukotriene A4

  • Furthermore, formation of 14,15-leukotriene A4 was inferred from the characteristic pattern of its hydrolysis products comprised of equal amounts of (8R,15S)- and (8S,15S)-dihydroxy-5Z,9E,11E,13E-eicosatetraenoi c acids together with smaller amounts of (14R,15S)-erythro- and (14S,15S)-threo-dihydroxy-5Z,8Z,10E,12E-eicosate traenoic acids [1].
  • The results support a mechanism whereby 14,15-leukotriene A4 is synthesized from 15-HPETE by a further enzymatic step carried out by the reticulocyte 15-lipoxygenase via hydrogen abstraction at C-10 and a redox cycle of the non-heme iron atom of the enzyme [2].
  • The observation that endothelial cells can synthesize both 15-HETE and 8,15-diHETE molecules suggests that this cell type contains both a 15-lipoxygenase and a system that can synthesize 14,15-leukotriene A4 [3].
  • Intact 14,15-leukotriene A4 then decomposes by first-order kinetics with rate constants inversely proportional to the albumin concentration [4].
  • When 14C-labeled (14S, 15S)-14,15-trans-oxido-5,8-cis-10,12-trans-eicosatetraenoic acid (14,15-leukotriene A4) was incubated with cytosolic epoxide hydrolase purified from mouse liver, one major radiolabeled product appeared [5].

Anatomical context of 14,15-Leukotriene A4


Associations of 14,15-Leukotriene A4 with other chemical compounds


  1. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. Yokoyama, C., Shinjo, F., Yoshimoto, T., Yamamoto, S., Oates, J.A., Brash, A.R. J. Biol. Chem. (1986) [Pubmed]
  2. 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]
  3. Biosynthesis and metabolism of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid by human umbilical vein endothelial cells. Hopkins, N.K., Oglesby, T.D., Bundy, G.L., Gorman, R.R. J. Biol. Chem. (1984) [Pubmed]
  4. Albumin stabilizes 14,15-leukotriene A4. Haeggström, J., Fitzpatrick, F., Rådmark, O., Samuelsson, B. FEBS Lett. (1983) [Pubmed]
  5. 14,15-Dihydroxy-5,8,10,12-eicosatetraenoic acid. Enzymatic formation from 14,15-leukotriene A4. Wetterholm, A., Haeggström, J., Hamberg, M., Meijer, J., Rådmark, O. Eur. J. Biochem. (1988) [Pubmed]
  6. Investigation of the selectivity of hydrogen abstraction in the nonenzymatic formation of hydroxyeicosatetraenoic acids and leukotrienes by autoxidation. Brash, A.R., Porter, A.T., Maas, R.L. J. Biol. Chem. (1985) [Pubmed]
  7. Identification of lipoxygenase products from arachidonic acid metabolism in stimulated murine eosinophils. Turk, J., Rand, T.H., Maas, R.L., Lawson, J.A., Brash, A.R., Roberts, L.J., Colley, D.G., Oates, J.A. Biochim. Biophys. Acta (1983) [Pubmed]
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