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08-SEPTEMBER-2008 09:13:22 - Lipoxin Lipoxin B4 Lipoxin B4 IUPAC name 5S,14R,15S-Trihydroxy-6E,8Z,10E,12E -eicosatetraenoic acid Other names LXB4 Identifiers CAS number 92950-25-9 PubChem 5280915 SMILES CCCCCCCC=CC=CC=CC=CCCCCC=OOOOO Properties Molecular formula C20H32O5 Molar mass 352.46508 g/mol Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Lipoxin A4 Lipoxin A4 Lipoxins are a series of anti-inflammatory mediators. Lipoxins are short lived endogenously produced nonclassic eicosanoids whose appearance in inflammation signals the resolution of inflammation. They are abbreviated as LX, an acronym for lipoxygenase LO interaction products. At present two lipoxins have been identified; lipoxin A4 LXA4 and lipoxin B4 LXB4. Contents 1 History 2 Biosynthesis 3 Biological activity 3.1 In resolution 3.2 Lipoxin analogues 4 References 5 External links History Lipoxins were first described by Serhan, Hamberg and Samuelsson in 1984.1 They reported that the lipoxins stimulated superoxide anion O2- generation and degranulation at submicromolar concentrations-as potent as LTB4. Biosynthesis Lipoxins are derived enzymatically from arachidonic acid, an ω-6 fatty acid. An analogous class, the resolvins, is derived from EPA and DHA, ω-3 fatty acids.1 Another analogous class, the epi-lipoxins, is formed by non-enzymatic peroxidation. Biological activity Lipoxins, as well as certain peptides, are high affinity ligands for the lipoxin A4 receptor LXA4R, which was first identified based on sequence homology as the formyl peptide receptor like receptor FPRL1. Lipoxin signaling through the LXA4R inhibits chemotaxis, transmigration, superoxide generation and NF-κB activation.2 Conversely, peptide signaling through the same receptor, in vitro, has been shown to stimulate chemotaxis of polymorphonuclear cells PMNs and calcium mobilization.2 The peptides that have ALXR affinity tend to be signals for leukocyte migration and subsequent phagocytosis such as acute phase proteins, bacterial peptides, HIV envelope proteins and neurotoxic peptides. Similarly to the leukotrienes, LXA4 will form the cysteinyl-lipoxins LXC4, LXD4 and LXE4.3 At subnanomolar concentrations, LXA4 and LXB4 inhibit leukotriene-stimulated interactions of human neutrophils and endothelial cells.4 Lipoxins are high affinity antagonists to the cysteinyl leukotriene receptor type 1 CysLT1 to which several leukotrienes LTC4, LTD4 and LTE4 mediate their smooth muscle contraction and eosinophil chemotactic effects. The CysLT1 receptor is also the site of action for the asthma drug montelukast Singulair.5 In resolution During inflammation, cells die by apoptosis. As part of resolution, lipoxins signal macrophages to the remains of these cells phagocytosis.6 During the acute inflammatory process, the proinflammatory cytokines such as IFN-γ and IL-1β can induce the expression of anti-inflammatory mediators such as lipoxins and IL-4, which promote the resolution phase of inflammation.7 Lipoxin analogues Stable synthetic analogues of LXs and aspirin-triggered 15-epi-LXA4s ATLs can mimic many of the desirable anti-inflammatory, pro-resolution actions of native LXs.8 References ^ a b Charles N. Serhan, Mats Hamberg, and Bengt Samuelsson September 1, 1984. Lipoxins: Novel Series of Biologically Active Compounds Formed from Arachidonic Acid in Human Leukocytes pdf. Retrieved on 2006-02-02. Original description of lipoxins. ^ a b Chiang N., Arita M., and Serhan CN. 2005. Anti-inflammatory circuitry: Lipoxin, aspirin-triggered lipoxins and their receptor ALX. Retrieved on 2006-04-28. ^ Powell WS, Chung D, Gravel S 1995. 5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent stimulator of human eosinophil migration. J. Immunol. 154 8: 4123-32. PMID 7706749. ^ Papayianni A, Serhan CN, Brady HR 1996. Lipoxin A4 and B4 inhibit leukotriene-stimulated interactions of human neutrophils and endothelial cells. J. Immunol. 156 6: 2264-72. PMID 8690917. Retrieved on 2007-11-01. ^ Drazen J., Israel E., and O'Byrne P. 1999. Treatment of Asthma with Drugs Modifying the Leukotriene Pathway. PMID 9895400. Retrieved on 2006-04-28. ^ Mitchell S, Thomas G, Harvey K, et al 2002. Lipoxins, aspirin-triggered epi-lipoxins, lipoxin stable analogues, and the resolution of inflammation: stimulation of macrophage phagocytosis of apoptotic neutrophils in vivo. J. Am. Soc. Nephrol. 13 10: 2497-507. doi:10.1097/01.ASN.0000032417.73640.72. PMID 12239238. ^ McMahon, Blaithin and Godson, Catherine. Lipoxins: endogenous regulators of inflammation. Retrieved on 2006-02-07. Invited review article. ^ McMahon B, Mitchell S, Brady HR 2001. Lipoxins: revelations on resolution. Trends Pharmacol. Sci. 22 8: 391-5. doi:10.1016/S0165-61470001771-5. PMID 11478982. External links MeSH Lipoxins v d e Autacoids, unsaturated fatty acids: Eicosanoids Prostanoids Prostaglandins - Thromboxanes A2, B2 Leukotrienes A4 - B4 - Slow reacting substance of anaphylaxis C4, D4, E4 Other Arachidonic acids - Eicosapentaenoic acid - Lipoxins Retrieved from http://en..org/wiki/Lipoxin Categories: 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 15 July 2008, at 10:11
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