Hepoxilin

Hepoxilin

Chembox new
ImageFile=Hepoxilin A3.pngImageSize=
Name=Hepoxilin A3
IUPACName=(5E,9E)-8-hydroxy-10- [3- [(E)-oct-2-enyl] -2-oxiranyl] deca-5,9-dienoic acid
OtherNames= HXA3
Section1= Chembox Identifiers
CASNo=
PubChem=5353666
SMILES=CCCCCC=CCC1C(O1)C=CC(CC=CCCCC(=O)O)O
Section2= Chembox Properties
Formula=C20H32O4
MolarMass=336.46568
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition= 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.cite journal |author=Pace-Asciak CR, Martin JM |title=Hepoxilin, a new family of insulin secretagogues formed by intact rat pancreatic islets |journal=Prostaglandins, leukotrienes, and medicine |volume=16 |issue=2 |pages=173–80 |year=1984 |pmid=6396652 |doi=]

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 EPAcite journal |author=Pace-Asciak CR |title=Formation of hepoxilin A4, B4 and the corresponding trioxilins from 12(S)-hydroperoxy-5,8,10,14,17-icosapentaenoic acid |journal=Prostaglandins, leukotrienes, and medicine |volume=22 |issue=1 |pages=1–9 |year=1986 |pmid=3012585 |doi=]

Physiological effect

In the skin, Hx are pro-inflammatory, but in neutrophils they are anti-inflammatory.cite web|title = LEUKOTRIENES AND LIPOXINS: Chemistry and Biology
url = http://www.lipidlibrary.co.uk/Lipids/eic_leuk/index.htm
accessdate = January 4
accessyear = 2007
author = Christie, William W.
year = 2006] Hx are potent insulin secretagogues.One hepoxilin, HepA3, mediates neutrophil migration across the intestines.cite web
title= Identification of hepoxilin A3 in inflammatory events: A required role in neutrophil migration across intestinal epithelia
author = Randall J. Mrsny, Andrew T. Gewirtz, Dario Siccardi, Tor Savidge , Bryan P. Hurley , James L. Madara, and Beth A. McCormick
journal = Proceedings of the National Academy of Sciences of the United States of America
accessdate = January 4
accessyear = 2007
year = 2004
url = http://www.pnas.org/cgi/content/full/101/19/7421] Hepoxilins are also produced in the brain.cite journal|author=Piomelli, Daniele |title=Arachidonic Acid
url= http://www.acnp.org/g4/GN401000059/Default.htm
year= 2000|accessdate=2006-03-03|work=Neuropsychopharmacology: The Fifth Generation of Progress] Cells under oxidative stress secrete HX3, which in turn upregulates peroxidase, decreasing oxidative stress. This is proposed toconstitute a compensatory defense response to protect the vitality and functionality of the cell.cite journal |url=http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6WPH-4R2XCKC-1&_user=2148702&_coverDate=11%2F30%2F2007&_rdoc=12&_fmt=summary&_orig=browse&_srch=doc-info(%23toc%236991%232007%23999229996%23675187%23FLA%23display%23Volume)&_cdi=6991&_sort=d&_docanchor=&_ct=13&_acct=C000056362&_version=1&_urlVersion=0&_userid=2148702&md5=1415a8d346b3ff51f96d7776f19b658a |title=Prostaglandins, Leukotrienes and Essential Fatty Acids : Biological role of hepoxilins: Upregulation of phospholipid hydroperoxide glutathione peroxidase as a cellular response to oxidative stress? |accessdate=2007-12-04 |format= |work=
journal=Prostaglandins, Leukotrienes and Essential Fatty Acids |author=M.P. Zafiriou "et al"
volume= 77 |issue=3-4|date=October-November 2007|pages =209–215 |doi=10.1016/j.plefa.2007.08.007]

References


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