Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-13 17:56:48 UTC |
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Update Date | 2022-07-12 23:05:07 UTC |
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HMDB ID | HMDB0004385 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Lipoxin A4 |
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Description | Lipoxin A4 (LXA4) was first identified in 1984 by Serhan and colleagues as 5-lipoxygenase interaction product of activated leukocytes. Endogenous transcellular biosynthesis of LXA4 occurs via interaction of leukocytes with epithelium, endothelium or platelets. Lipoxins (LXs) or the lipoxygenase interaction products are generated from arachidonic acid via sequential actions of lipoxygenases and subsequent reactions to give specific trihydroxytetraene-containing eicosanoids. These unique structures are formed during cell-cell interactions and appear to act at both temporal and spatially distinct sites from other eicosanoids produced during the course of inflammatory responses and to stimulate natural resolution. Lipoxin A4 (LXA4) and lipoxin B4 (LXB4) are positional isomers that each possesses potent cellular and in vivo actions. These LX structures are conserved across species. The results of numerous studies reviewed in this work now confirm that they are the first recognized eicosanoid chemical mediators that display both potent anti-inflammatory and pro-resolving actions in vivo in disease models that include rabbit, rat, and mouse systems. LXs act at specific GPCRs as agonists to regulate cellular responses of interest in inflammation and resolution. Aspirin has a direct impact in the LX circuit by triggering the biosynthesis of endogenous epimers of LX, termed the aspirin-triggered 15-epi-LX, that share the potent anti-inflammatory actions of LX. (PMID: 16005201 , 16613568 ). |
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Structure | CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1 |
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Synonyms | Value | Source |
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(5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid | ChEBI | (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid | ChEBI | (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoic acid | ChEBI | (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid | ChEBI | 5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoic acid | ChEBI | 5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid | ChEBI | 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid | ChEBI | 5S,6R-LipoxinA4 | ChEBI | 6R-LXA4 | ChEBI | LXA4 | ChEBI | (5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate | Generator | (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoate | Generator | (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoate | Generator | (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate | Generator | 5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoate | Generator | 5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate | Generator | 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoate | Generator | 5S,6S-Lipoxin a4 | HMDB | 15-Epi-lxa4 | HMDB | 15-Epi-lipoxin a4 | HMDB | 5,6,15-Tri-hete | HMDB | 5,6,15-TriHETE | HMDB | 5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid | HMDB |
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Chemical Formula | C20H32O5 |
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Average Molecular Weight | 352.4651 |
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Monoisotopic Molecular Weight | 352.224974134 |
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IUPAC Name | (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid |
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Traditional Name | lipoxin A4 |
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CAS Registry Number | 89663-86-5 |
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SMILES | CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1 |
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InChI Key | IXAQOQZEOGMIQS-SSQFXEBMSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lipoxins. These are eicosanoids with a trihydroxyicosatetraenoic acid skeleton (a c20-fatty acid, with the chain bearing three hydroxyl groups and four double bonds). Lipoxins have four double bonds, which are all conjugated. In some cases a hydroxyl group is substituted by a C=O group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Eicosanoids |
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Direct Parent | Lipoxins |
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Alternative Parents | |
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Substituents | - Lipoxin
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Polyol
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Lipoxin A4,1TMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C | 3198.8 | Semi standard non polar | 33892256 | Lipoxin A4,1TMS,isomer #2 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O | 3157.1 | Semi standard non polar | 33892256 | Lipoxin A4,1TMS,isomer #3 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C | 3154.4 | Semi standard non polar | 33892256 | Lipoxin A4,1TMS,isomer #4 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C | 3112.7 | Semi standard non polar | 33892256 | Lipoxin A4,2TMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C | 3188.5 | Semi standard non polar | 33892256 | Lipoxin A4,2TMS,isomer #2 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3182.2 | Semi standard non polar | 33892256 | Lipoxin A4,2TMS,isomer #3 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3156.1 | Semi standard non polar | 33892256 | Lipoxin A4,2TMS,isomer #4 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C | 3175.2 | Semi standard non polar | 33892256 | Lipoxin A4,2TMS,isomer #5 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C | 3109.6 | Semi standard non polar | 33892256 | Lipoxin A4,2TMS,isomer #6 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3105.1 | Semi standard non polar | 33892256 | Lipoxin A4,3TMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3187.2 | Semi standard non polar | 33892256 | Lipoxin A4,3TMS,isomer #2 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3143.5 | Semi standard non polar | 33892256 | Lipoxin A4,3TMS,isomer #3 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3130.5 | Semi standard non polar | 33892256 | Lipoxin A4,3TMS,isomer #4 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3127.3 | Semi standard non polar | 33892256 | Lipoxin A4,4TMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3155.9 | Semi standard non polar | 33892256 | Lipoxin A4,1TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3450.6 | Semi standard non polar | 33892256 | Lipoxin A4,1TBDMS,isomer #2 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O | 3413.6 | Semi standard non polar | 33892256 | Lipoxin A4,1TBDMS,isomer #3 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3408.0 | Semi standard non polar | 33892256 | Lipoxin A4,1TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 3377.5 | Semi standard non polar | 33892256 | Lipoxin A4,2TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3676.6 | Semi standard non polar | 33892256 | Lipoxin A4,2TBDMS,isomer #2 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3675.1 | Semi standard non polar | 33892256 | Lipoxin A4,2TBDMS,isomer #3 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3667.6 | Semi standard non polar | 33892256 | Lipoxin A4,2TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3671.2 | Semi standard non polar | 33892256 | Lipoxin A4,2TBDMS,isomer #5 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 3619.3 | Semi standard non polar | 33892256 | Lipoxin A4,2TBDMS,isomer #6 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3616.4 | Semi standard non polar | 33892256 | Lipoxin A4,3TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3954.0 | Semi standard non polar | 33892256 | Lipoxin A4,3TBDMS,isomer #2 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3914.5 | Semi standard non polar | 33892256 | Lipoxin A4,3TBDMS,isomer #3 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3913.7 | Semi standard non polar | 33892256 | Lipoxin A4,3TBDMS,isomer #4 | CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3903.6 | Semi standard non polar | 33892256 | Lipoxin A4,4TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4175.2 | Semi standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Lipoxin A4 GC-MS (Non-derivatized) - 70eV, Positive | splash10-02ti-3942000000-539dee31c556f111beef | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lipoxin A4 GC-MS (4 TMS) - 70eV, Positive | splash10-004i-9023156000-8244ac03abe716c2ce53 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lipoxin A4 GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Lipoxin A4 LC-ESI-QQ , negative-QTOF | splash10-0fri-0796000000-05d19d6a20bf1380d76e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lipoxin A4 LC-ESI-QQ , negative-QTOF | splash10-0avl-0985000000-f36e867fda44da442a8e | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Positive-QTOF | splash10-00kr-0019000000-19caadde5e524b5ae250 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Positive-QTOF | splash10-00kr-9466000000-dc971dc55975b569912b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Positive-QTOF | splash10-000f-9430000000-bc82bb195c4947fa53cf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Negative-QTOF | splash10-0udi-0009000000-009f9c82d818546c6102 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Negative-QTOF | splash10-0kai-4379000000-52c1e5333adc5555ffef | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Negative-QTOF | splash10-0a4i-9340000000-ca0cb5410468b7dee5f8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Negative-QTOF | splash10-0ue9-0009000000-cb99b6286e5f411abaa3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Negative-QTOF | splash10-0gc0-4459000000-b29437cc7614015ca29b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Negative-QTOF | splash10-014j-9320000000-477457ab7d09daaade6b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Positive-QTOF | splash10-014r-0119000000-a8a3218eed37097e38da | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Positive-QTOF | splash10-00kr-1936000000-0ece3e36fd898b1f9097 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Positive-QTOF | splash10-059f-9600000000-18d8014a43feca3a38b6 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | <0.00007 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000104 +/- 0.000119 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <0.00007 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000053 +/- 0.000013 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.044 +/- 0.0068 uM | Adult (>18 years old) | Both | Coronary artery disease | | details |
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Associated Disorders and Diseases |
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Disease References | Coronary artery disease |
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- Brezinski DA, Nesto RW, Serhan CN: Angioplasty triggers intracoronary leukotrienes and lipoxin A4. Impact of aspirin therapy. Circulation. 1992 Jul;86(1):56-63. [PubMed:1617790 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023370 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4444429 |
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KEGG Compound ID | C06314 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Lipoxin |
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METLIN ID | 7058 |
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PubChem Compound | 5280914 |
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PDB ID | Not Available |
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ChEBI ID | 6498 |
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Food Biomarker Ontology | Not Available |
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VMH ID | C06314 |
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MarkerDB ID | MDB00000449 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J.; Lee, T. H. Total synthesis of lipoxin A4 and lipoxin B4 from butadiene. Tetrahedron Letters (2000), 41(6), 823-826. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Nicolaou KC, Marron BE, Veale CA, Webber SE, Dahlen SE, Samuelsson B, Serhan CN: Identification of a novel 7-cis-11-trans-lipoxin A4 generated by human neutrophils: total synthesis, spasmogenic activities and comparison with other geometric isomers of lipoxins A4 and B4. Biochim Biophys Acta. 1989 May 15;1003(1):44-53. [PubMed:2713393 ]
- Wu SH, Wu XH, Lu C, Dong L, Chen ZQ: Lipoxin A4 inhibits proliferation of human lung fibroblasts induced by connective tissue growth factor. Am J Respir Cell Mol Biol. 2006 Jan;34(1):65-72. Epub 2005 Sep 1. [PubMed:16141446 ]
- Moores KE, Merritt JE: Lipoxin A4 elevates cytosolic calcium in human neutrophils. Eicosanoids. 1991;4(2):89-94. [PubMed:1910866 ]
- Sumimoto H, Isobe R, Mizukami Y, Minakami S: Formation of a novel 20-hydroxylated metabolite of lipoxin A4 by human neutrophil microsomes. FEBS Lett. 1993 Jan 11;315(3):205-10. [PubMed:8422907 ]
- Bae YS, Park JC, He R, Ye RD, Kwak JY, Suh PG, Ho Ryu S: Differential signaling of formyl peptide receptor-like 1 by Trp-Lys-Tyr-Met-Val-Met-CONH2 or lipoxin A4 in human neutrophils. Mol Pharmacol. 2003 Sep;64(3):721-30. [PubMed:12920210 ]
- Tran U, Boyle T, Shupp JW, Hammamieh R, Jett M: Staphylococcal enterotoxin B initiates protein kinase C translocation and eicosanoid metabolism while inhibiting thrombin-induced aggregation in human platelets. Mol Cell Biochem. 2006 Aug;288(1-2):171-8. Epub 2006 Mar 21. [PubMed:16550298 ]
- Parkinson JF: Lipoxin and synthetic lipoxin analogs: an overview of anti-inflammatory functions and new concepts in immunomodulation. Inflamm Allergy Drug Targets. 2006 Apr;5(2):91-106. [PubMed:16613568 ]
- Andersson P, Serhan CN, Petasis NA, Palmblad J: Interactions between lipoxin A4, the stable analogue 16-phenoxy-lipoxin A4 and leukotriene B4 in cytokine generation by human monocytes. Scand J Immunol. 2004 Sep;60(3):249-56. [PubMed:15320881 ]
- Serhan CN: Lipoxins and aspirin-triggered 15-epi-lipoxins are the first lipid mediators of endogenous anti-inflammation and resolution. Prostaglandins Leukot Essent Fatty Acids. 2005 Sep-Oct;73(3-4):141-62. [PubMed:16005201 ]
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