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Eoxin A4

Eoxin A4, also known as 14,15-leukotriene A4, is an eoxin. Cells make eoxins by metabolizing arachidonic acid with a 15-lipoxygenase enzyme to form 15(S)-hydroperoxyeicosapentaenoic acid (i.e. 15(S)-HpETE). This product is then converted serially to eoxin A4 (i.e. EXA4), EXC4, EXD4, and EXE4 by LTC4 synthase, an unidentified gamma-glutamyltransferase, and an unidentified dipeptidase, respectively, in a pathway which appears similar if not identical to the pathway which forms leukotreines, i.e. LTA4, LTC4, LTD4, and LTE4. This pathway is schematically shown as follows:[1][2]

Eoxin A4
Names
Preferred IUPAC name
(5Z,8Z,10E,12E)-13-[(2S,3S)-3-Pentyloxiran-2-yl]trideca-5,8,10,12-tetraenoic acid
Other names
EXa4; 14,15-LTA4
Identifiers
  • 81918-96-9 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:63983
ChemSpider
  • 27471348
  • 52921883
  • InChI=1S/C20H30O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-10,13,16,18-19H,2-3,5,11-12,14-15,17H2,1H3,(H,21,22)/b6-4-,9-7-,10-8+,16-13+/t18-,19-/m0/s1
    Key: URDQSJSEGRMOIT-FDMWOPBLSA-N
  • CCCCC[C@H]1[C@@H](O1)/C=C/C=C/C=C\C/C=C\CCCC(=O)O
Properties
C20H30O3
Molar mass 318.457 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Arachidonic acid + O2 → 15(S)-HpETE → EXA4 → EXC4 → EXD4 → EXE4

EXA4 is viewed as an intracellular-bound, short-lived intermediate which is rapidly metabolized to the down-stream eoxins. The eoxins down stream of EXA4 are secreted from their parent cells and, it is proposed but not yet proven, serve to regulate allergic responses and the development of certain cancers (see Eoxins).[1][3]

References edit

  1. ^ a b Claesson HE (September 2009). "On the biosynthesis and biological role of eoxins and 15-lipoxygenase-1 in airway inflammation and Hodgkin lymphoma". Prostaglandins Other Lipid Mediat. 89 (3–4): 120–5. doi:10.1016/j.prostaglandins.2008.12.003. PMID 19130894.
  2. ^ Greene ER, Huang S, Serhan CN, Panigrahy D (2011). "Regulation of inflammation in cancer by eicosanoids". Prostaglandins & Other Lipid Mediators. 96 (1–4): 27–36. doi:10.1016/j.prostaglandins.2011.08.004. PMC 4051344. PMID 21864702.
  3. ^ Feltenmark S, Gautam N, Brunnström A, Griffiths W, Backman L, Edenius C, Lindbom L, Björkholm M, Claesson HE (2008). "Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells". Proceedings of the National Academy of Sciences of the United States of America. 105 (2): 680–5. Bibcode:2008PNAS..105..680F. doi:10.1073/pnas.0710127105. PMC 2206596. PMID 18184802.


eoxin, also, known, leukotriene, eoxin, cells, make, eoxins, metabolizing, arachidonic, acid, with, lipoxygenase, enzyme, form, hydroperoxyeicosapentaenoic, acid, hpete, this, product, then, converted, serially, eoxin, exa4, exc4, exd4, exe4, ltc4, synthase, u. Eoxin A4 also known as 14 15 leukotriene A4 is an eoxin Cells make eoxins by metabolizing arachidonic acid with a 15 lipoxygenase enzyme to form 15 S hydroperoxyeicosapentaenoic acid i e 15 S HpETE This product is then converted serially to eoxin A4 i e EXA4 EXC4 EXD4 and EXE4 by LTC4 synthase an unidentified gamma glutamyltransferase and an unidentified dipeptidase respectively in a pathway which appears similar if not identical to the pathway which forms leukotreines i e LTA4 LTC4 LTD4 and LTE4 This pathway is schematically shown as follows 1 2 Eoxin A4 NamesPreferred IUPAC name 5Z 8Z 10E 12E 13 2S 3S 3 Pentyloxiran 2 yl trideca 5 8 10 12 tetraenoic acidOther names EXa4 14 15 LTA4IdentifiersCAS Number 81918 96 9 Y3D model JSmol Interactive imageChEBI CHEBI 63983ChemSpider 27471348PubChem CID 52921883InChI InChI 1S C20H30O3 c1 2 3 12 15 18 19 23 18 16 13 10 8 6 4 5 7 9 11 14 17 20 21 22 h4 6 10 13 16 18 19H 2 3 5 11 12 14 15 17H2 1H3 H 21 22 b6 4 9 7 10 8 16 13 t18 19 m0 s1Key URDQSJSEGRMOIT FDMWOPBLSA NSMILES CCCCC C H 1 C H O1 C C C C C C C C C CCCC O OPropertiesChemical formula C 20H 30O 3Molar mass 318 457 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Arachidonic acid O2 15 S HpETE EXA4 EXC4 EXD4 EXE4 EXA4 is viewed as an intracellular bound short lived intermediate which is rapidly metabolized to the down stream eoxins The eoxins down stream of EXA4 are secreted from their parent cells and it is proposed but not yet proven serve to regulate allergic responses and the development of certain cancers see Eoxins 1 3 References edit a b Claesson HE September 2009 On the biosynthesis and biological role of eoxins and 15 lipoxygenase 1 in airway inflammation and Hodgkin lymphoma Prostaglandins Other Lipid Mediat 89 3 4 120 5 doi 10 1016 j prostaglandins 2008 12 003 PMID 19130894 Greene ER Huang S Serhan CN Panigrahy D 2011 Regulation of inflammation in cancer by eicosanoids Prostaglandins amp Other Lipid Mediators 96 1 4 27 36 doi 10 1016 j prostaglandins 2011 08 004 PMC 4051344 PMID 21864702 Feltenmark S Gautam N Brunnstrom A Griffiths W Backman L Edenius C Lindbom L Bjorkholm M Claesson HE 2008 Eoxins are proinflammatory arachidonic acid metabolites produced via the 15 lipoxygenase 1 pathway in human eosinophils and mast cells Proceedings of the National Academy of Sciences of the United States of America 105 2 680 5 Bibcode 2008PNAS 105 680F doi 10 1073 pnas 0710127105 PMC 2206596 PMID 18184802 nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Eoxin A4 amp oldid 1119001352, wikipedia, wiki, book, books, library,

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