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Hepoxilin

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Hepoxilin A3
Names
IUPAC name (5E,9E)-8-hydroxy-10- -2-oxiranyl]deca-5,9-dienoic acid
Other names HXA3
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • CCCCCC=CCC1C(O1)C=CC(CC=CCCCC(=O)O)O
Properties
Chemical formula C20H32O4
Molar mass 336.47 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Hepoxilins (HxA3 and HxB3) are nonclassic eicosanoid hormones involved in inflammation.

History

Hepoxilins were identified and named in Canada in 1984 by CR Pace-Asciak and JM Martin.

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

Physiological effect

In the skin, Hx are pro-inflammatory, but in neutrophils they are anti-inflammatory. Hx are potent insulin secretagogues. One hepoxilin, HepA3, mediates neutrophil migration across the intestines. Hepoxilins are also produced in the brain. 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.

References

  1. 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. doi:10.1016/0262-1746(84)90069-6. PMID 6396652.
  2. ^ Pace-Asciak CR (1986). "Formation of hepoxilin A4, B4 and the corresponding trioxilins from 12(S)-hydroperoxy-5,8,10,14,17-icosapentaenoic acid". Prostaglandins, leukotrienes, and medicine. 22 (1): 1–9. doi:10.1016/0262-1746(86)90017-X. PMID 3012585.
  3. Christie, William W. (2006). "LEUKOTRIENES AND LIPOXINS: Chemistry and Biology". Retrieved January 4, 2007.
  4. 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". Proceedings of the National Academy of Sciences of the United States of America. 101 (19): 7421–6. doi:10.1073/pnas.0400832101. PMC 409934. PMID 15123795. Retrieved January 4, 2007.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Piomelli, Daniele (2000). "Arachidonic Acid". Neuropsychopharmacology: The Fifth Generation of Progress. New York: Chapman & Hall. ISBN 0412109514. Retrieved 2006-03-03.
  6. 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. PMID 17997296. Retrieved 2007-12-04. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: date format (link)
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