Eoxin A₄

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
CAS Number	81918-96-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:63983;
ChemSpider	27471348;
PubChem CID	52921883;
CompTox Dashboard (EPA)	DTXSID801032105 ;
	InChI 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;
	SMILES CCCCC[C@H]1[C@@H](O1)/C=C/C=C/C=C\C/C=C\CCCC(=O)O;
Properties
Chemical formula	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). Infobox references

Eoxin A₄ (EXA₄), 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 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]

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 downstream eoxins. The eoxins downstream 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

^ ^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 & Other Lipid Mediators. 96 (1–4): 27–36. doi:10.1016/j.prostaglandins.2011.08.004. PMC 4051344. PMID 21864702.
^ 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.

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[15-LOX-1_review-1] 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.

[pmid21864702-2] 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.

[pmid18184802-3] 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.

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