Lipoxin
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| Names | |
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IUPAC name
5S,14R,15S-Trihydroxy-6E,8Z,10E,12E -eicosatetraenoic acid
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| Other names
LXB4
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| Identifiers | |
92950-25-9 
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| 3D model (Jmol) | Interactive image |
| ChEBI |
CHEBI:6499
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| ChemSpider |
4444430
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| 5216 | |
| PubChem | 5280915 |
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| Properties | |
| C20H32O5 | |
| Molar mass | 352.46508 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Lipoxins (LXs or Lxs), an acronym for lipoxygenase interaction products, are bioactive autacoid metabolites of arachidonic acid made by various cell types. They are categorized as nonclassic eicosanoids and members of the specialized pro-resolving mediators (SPMs) family of polyunsaturated fatty acid (PUFA) metabolites. Like other SPMs, LXs form during, and then act to resolve, inflammatory responses. Initially, two lipoxins were identified, lipoxin A4 (LXA4) and LXB4, but more recent studies have identified epimers of these two LXs viz., the epilipoxins, 15-epi-LXA4 and 15-epi-LXB4, respectively.
LXA4 and LXB4 were first described by Serhan, Hamberg, and the Nobel laurate Samuelsson in 1984. They reported that human blood neutrophils, when stimulated, make these two lipoxins and that neutrophils, when stimulated by either of the LX's, mounted superoxide anion (O2−) generation and degranulation responses. Both responses are considered to be pro-inflammatory in that, while aimed at neutralizing invading pathogens and digesting foreign material, can contribute to damaging host tissues and thereby prolonging and promoting further inflammation. Subsequent studies, however, found that these lipoxins, as well as their epimers, epi-LXA4 and LXB4, act primarily to dampen and resolve inflammation, i.e. they are anti-inflammatory cell signaling agents.
Lipoxins are derived enzymatically from arachidonic acid, an ω-6 fatty acid. Structurally, they are defined as arachidonic acid metabolites that contain three hydroxyl residues (also termed hydroxy residues) and four double bonds. This structural definition distinguishes them from other SPMs such as the resolvins, neuroprotectins, and maresins, which are metabolites of the omega 3 fatty acids, eicosapentaenoic acid or docosahexaenoic acid, as well as a range of metabolites derived from other PUFAs (see specialized pro-resolving mediators). All of these other SPMs have activities and functions similar, although not necessarily identical, to the lipoxins .
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