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08-SEPTEMBER-2008 09:13:22 - Hepoxilin Hepoxilin A3 IUPAC name 5E,9E-8-hydroxy-10-3-E-oct-2-enyl -2-oxiranyldeca-5,9-dienoic acid Other names HXA3 Identifiers CAS number PubChem 5353666 SMILES CCCCCC=CCC1CO1C=CCCC=CCCCC=OOO Properties Molecular formula C20H32O4 Molar mass 336.46568 Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Hepoxilins HxA3 and HxB3 are nonclassic eicosanoid hormones involved in inflammation. Contents 1 History 2 Biochemistry 3 Physiological effect 4 References History Hepoxilins were identified and named in Canada in 1984 by CR Pace-Asciak and JM Martin.1 Biochemistry They derive from arachidonic acid via oxidation by the enzyme 12-lipoxygenase. Hepoxilins are differentiated from closely related eicosanoids, the leukotrienes and the lipoxins, in that hepoxilins have no conjugated double bonds. Corresponding trioxlins A4 and B4 are formed by the same pathway from EPA 2 Physiological effect In the skin, Hx are pro-inflammatory, but in neutrophils they are anti-inflammatory.3 Hx are potent insulin secretagogues.2 One hepoxilin, HepA3, mediates neutrophil migration across the intestines.4 Hepoxilins are also produced in the brain.5 Cells under oxidative stress secrete HX3, which in turn upregulates peroxidase, decreasing oxidative stress. This is proposed to constitute a compensatory defense response to protect the vitality and functionality of the cell.6 References ^ Pace-Asciak CR, Martin JM 1984. Hepoxilin, a new family of insulin secretagogues formed by intact rat pancreatic islets. Prostaglandins, leukotrienes, and medicine 16 2: 173-80. PMID 6396652. ^ a b Pace-Asciak CR 1986. Formation of hepoxilin A4, B4 and the corresponding trioxilins from 12S-hydroperoxy-5,8,10,14,17-icosapentaenoic acid. Prostaglandins, leukotrienes, and medicine 22 1: 1-9. PMID 3012585. ^ Christie, William W. 2006. LEUKOTRIENES AND LIPOXINS: Chemistry and Biology. Retrieved on January 4, 2007. ^ Randall J. Mrsny, Andrew T. Gewirtz, Dario Siccardi, Tor Savidge , Bryan P. Hurley , James L. Madara, and Beth A. McCormick 2004. Identification of hepoxilin A3 in inflammatory events: A required role in neutrophil migration across intestinal epithelia. Retrieved on January 4, 2007. ^ Piomelli, Daniele 2000. Arachidonic Acid. Neuropsychopharmacology: The Fifth Generation of Progress. Retrieved on 2006-03-03. ^ M.P. Zafiriou et al October-November 2007. Prostaglandins, Leukotrienes and Essential Fatty Acids : Biological role of hepoxilins: Upregulation of phospholipid hydroperoxide glutathione peroxidase as a cellular response to oxidative stress?. Prostaglandins, Leukotrienes and Essential Fatty Acids 77 3-4: 209-215. doi:10.1016/j.plefa.2007.08.007. Retrieved on 2007-12-04. This biochemistry article is a stub. Retrieved from http://en..org/wiki/Hepoxilin Categories: Biochemistry stubs | Eicosanoids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page This page was last modified on 7 June 2008, at 11:32
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