Abstract
Multicellular host responses to infection, injury or inflammatory stimuli lead to the formation of lipid mediators (LMs) by the host (Cotran et al. 1994). The host response depends on a complex set of events that initiate inflammation and appear to be aimed at resolution.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Allison AC, Lafferty KJ, Fliri H (eds) (1993) Immunosuppressive and anti-inflammatory drugs. The New York Academy of Sciences, New York
Badr KF (1988) The glomerular physiology of lipoxin-A. Adv Exp Med Biol 229:131–136
Badr KF, Serhan CN, Nicolaou KC, Samuelsson B (1987) The action of lipoxin-A on glomerular microcirculatory dynamics in the rat. Biochem Biophys Res Commun 145:408–414
Badr KF, DeBoer DK, Schwartzberg M, Serhan CN (1989) Lipoxin A4 antagonizes cellular and in vivo actions of leukotriene D4 in rat glomerular mesangial cells: evidence for competition at a common receptor. Proc Natl Acad Sci U S A 86:3438–3442
Baldwin JM (1993) The probable arrangement of the helices in G protein-coupled receptors. EMBO J 12:1693–1703
Bao L, Gerard NP, Eddy RL Jr, Shows TB, Gerard C (1992) Mapping of genes for the human C5a receptor (C5AR), human fMLP receptor (FPR), and two fMLP receptor homologue orphan rceptors (FPRH1, FPRH2) to chromosome 19. Genomics 13:437–440
Barrett KE, Bigby TD (1993) The intestinal epithelium: a participant in as well as the target of inflammation? Gastroenterology 105:302–303
Beckman BS, Despinasse BP, Spriggs L (1992) Actions of lipoxins A4 and B4 on signal transduction events in Friend erythroleukemia cells. Proc Soc Exp Biol Med 201:169–173
Brezinski DA, Serhan CN (1991) Characterization of lipoxins by combined gas chromatography and electron-capture negative ion chemical ionization mass spectrometry: formation of lipoxin A4 by stimulated human whole blood. Biol Mass Spectrom 20:45–52
Brezinski DA, Nesto RW, Serhan CN (1992) Angioplasty triggers intracoronary leukotrienes and lipoxin A4. Impact of aspirin therapy. Circulation 86:56–63
Busija DW, Armstead W, Leffler CW, Mirro R (1989) Lipoxins A4 and B4 dilate cerebral arterioles of newborn pigs. Am J Physiol 256:H468-H471
Chavis C, Chanez P, Vachier I, Bousquet J, Michel FB, Godard P (1995) 5,15diHETE and lipoxins generated by neutrophils from endogenous arachi- donic acid as asthma biomarkers. Biochem Biophys Res Commun 207:273–279
Chavis C, Vachier I, Chanez P, Bousquet J, Godard P (1996) 5(S),15(S)-Dihydroxyeicosatetraenoic acid and lipoxin generation in human polymorphonuclear cells: dual specificity of 5-lipoxygenase towards endogenous and exogenous precursors. J Exp Med 183:1633–1643
Chiang N, Takano T, Clish CB, Petasis NA, Tai H-H, Serhan CN (1998) Aspirin-triggered 15-epi-lipoxin A4 (ATL) generation by human leukocytes and murine peritonitis exudates: Development of a specific 15-epi-LXA4 ELISA. J Pharmacol Exp Ther 287:779–790
Christie PE, Spur BW, Lee TH (1992) The effects of lipoxin A4 on airway responses in asthmatic subjects. Am Rev Respir Dis 145:1281–1284
Chungaon KO, Soyombo O, Spur BW, Lee TH (1996) Stimulation of protein kinase C redistribution and inhibition of leukotriene B4-induced inositol 1,4,5-trisphosphate generation in human neutrophils by lipoxin A4. Br J Pharmacol 117:13 34–1340
Clària J, Serhan CN (1995) Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. Proc Natl Acad Sci U S A 92:9475–9479
Clària J, Lee MH, Serhan CN (1996) Aspirin-triggered lipoxins (15-epi-LX) are generated by the human lung adenocarcinoma cell line (A549)-neutrophil interactions and are potent inhibitors of cell proliferation. Mol Med 2:583–596
Clària J, Titos E, Jiménez W, Ros J, Ginès P, Arroyo V, Rivera F, Rodés J (1998) Altered biosynthesis of leukotrienes and lipoxins and host defense disorders in patients with cirrhosis and ascites. Gastroenterology 115:147–156
Clish CB, O’Brien JA, Gronert K, Stahl GL, Petasis NA, Serhan CN (1999) Local and systemic delivery of a stable aspirin-triggered lipoxin prevents neutrophil recruitment in vivo. Proc Natl Acad Sci U S A 96:8247–8252
Coleman RA, Smith WL, Narumiya S (1994) International Union of Pharmacology classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol Rev 46:205–229
Colgan SP, Serhan CN, Parkos CA, Delp-Archer C, Madara JL (1993) Lipoxin A4 modulates transmigration of human neutrophils across intestinal epithelial monolayers. J Clin Invest 92:75–82
Cotran RS, Kumar V, Robbins SL (1994) Robbins pathologic basis of disease. Saunders, Philadelphia
Dahlén S-E, Serhan CN (1991) Lipoxins: bioactive lipoxygenase interaction products. In: Wong A, Crooke ST (eds) Lipoxygenases and their products. Academic, San Diego, p 235
Dahlén SE, Raud J, Serhan CN, Björk J, Samuelsson B (1987) Biological activities of lipoxin A include lung strip contraction and dilation of arterioles in vivo. Acta Physiol Scand 130:643–647
Dahlén SE, Franzén L, Raud J, Serhan CN, Westlund P, Wikström E, Björck T, Matsuda H, Webber SE, Veale CA, Puustinen T, Haeggström J, Nicolaou KC, Samuelsson B (1988) Actions of lipoxin A4 and related compounds in smooth muscle preparations and on the microcirculation in vivo. Adv Exp Med Biol 229:107–130
Dubois RN, Abramson SB, Crofford L, Gupta RA, Simon LS, Van de Putte LBA, Lipsky PE (1998) Cyclooxygenase in biology and disease. FASEB J 12:1063–1073
Edenius C, Kumlin M, Björk T, Anggard A, Lindgren JA (1990) Lipoxin formation in human nasal polyps and bronchial tissue. FEBS Lett 272:25–28
Feng Z, Godfrey HP, Mandy S, Strudwick S, Lin K-T, Heilman E, Wong PY K (1996) Leukotriene B4 modulates in vivo expression of delayed-type hypersensitivity by a receptor-mediated mechanism: regulation by lipoxin A4. J Pharmacol Exp Ther 278:950–956
Fiore S, Serhan CN (1989) Phospholipid bilayers enhance the stability of leukotriene A4 and epoxytetraenes: stabilization of eicosanoids by liposomes. Biochem Biophys Res Commun 159:477–481
Fiore S, Serhan CN (1990) Formation of lipoxins and leukotrienes during receptor-mediated interactions of human platelets and recombinant human granulocyte/macrophage colony-stimulating factor-primed neutrophils. J Exp Med 172:1451–1457
Fiore S, Serhan CN (1995) Lipoxin A4 receptor activation is distinct from that of the formyl peptide receptor in myeloid cells: inhibition of CD 11/18 expression by lipoxin A4—lipoxin A4 receptor interaction. Biochemistry 34:16678–16686
Fiore S, Ryeom SW, Weller PF, Serhan CN (1992) Lipoxin recognition sites. Specific binding of labeled lipoxin A4 with human neutrophils. J Biol Chem 267:16168–16176
Fiore S, Romano M, Reardon EM, Serhan CN (1993) Induction of functional lipoxin A4 receptors in HL-60 cells. Blood 81:3395–3403
Fiore S, Maddox JF, Perez HD, Serhan CN (1994) Identification of a human cDNA encoding a functional high affinity lipoxin A4 receptor. J Exp Med 180: 253–260
Gewirtz AT, McCormick B, Neish AS, Petasis NA, Gronert K, Serhan CN, Madara JL (1998) Pathogen-induced chemokine secretion from model intestinal epithelium is inhibited by lipoxin A4 analogs. J Clin Invest 101:1860–1869
Gewirtz AT, Fokin VV, Petasis NA, Serhan CN, Madara JL (1999) LXA4, aspirin-triggered 15-epi-LXA4, and their analogs selectively downregulate PMN azurophilic degranulation. Am J Physiol 276:C988–C994
Gillmor SA, Villasenor A, Fletterick R, Sigal E, Browner MF (1997) The structure of mammalian 15-lipoxygenase reveals similarity to the lipases and the determinants of substrate specificity. Nat Struct Biol 4:1003–1009
Grandordy BM, Lacroix H, Mavoungou E, Krilis S, Crea AE, Spur BW, Lee TH (1990) Lipoxin A4 inhibits phosphoinositide hydrolysis in human neutrophils. Biochem Biophys Res Commun 167:1022–1029
Gronert K, Virk SM, Herman CA (1995) Endogenous sulfidopeptide leukotriene synthesis and 12-lipoxygenase activity in bullfrog <i>(Rana catesbeiana)</i> erythrocytes. Biochim Biophys Acta 1255:311–319
Gronert K, Gewirtz A, Madara JL, Serhan CN (1998) Identification of a human enterocyte lipoxin A4 receptor that is regulated by IL-13 and IFN-γ and inhibits TNF-α-induced IL-8 release. J Exp Med 187:1285–1294
Hedqvist P, Raud J, Palmertz U, Haeggström J, Nicolaou KC, Dahlén SE (1989) Lipoxin A4 inhibits leukotriene B4-induced inflammation in the hamster cheek pouch. Acta Physiol Scand 137:571–572
Herschman HR (1996) Prostaglandin synthase 2. Biochim Biophys Acta 1299:125–140
Hill DJ, Griffiths DH, Rowley AF (1999) Trout thrombocytes contain 12- but not 5-lipoxygenase activity. Biochim Biophys Acta 1437:63–70
Huang W-W, Garcia-Zepeda EA, Sauty A, Oettgen HC, Rothenberg ME, Luster AD (1998) Molecular and biological characterization of the murine leukotriene B4 receptor expressed on eosinophils. J Exp Med 188:1063–1074
Kantha SS, Matsumura H, Kubo E, Kawase K, Takahata R, Serhan CN, Hayaishi O (1994) Effect of prostaglandin D2, lipoxins and leukotrienes on sleep and brain temperature of rats. Prostaglandins Leukot Essent Fatty Acids 51:87–93
Lee TH, Horton CE, Kyan-Aung U, Haskard D, Crea AE, Spur BW (1989) Lipoxin A4 and lipoxin B4 inhibit chemotactic responses of human neutrophils stimulated by leukotriene B4 and N-formyl-l-methionyl-l-leucyl-lphenylalanine. Clin Sci 77:195–203
Lee TH, Crea AE, Gant V, Spur BW, Marron BE, Nicolaou KC, Reardon E, Brezinski M, Serhan CN (1990) Identification of lipoxin A4 and its relationship to the sulfidopeptide leukotrienes C4, D4, and E4 in the bronchoalveolar lavage fluids obtained from patients with selected pulmonary diseases. Am Rev Respir Dis 141:1453–1458
Levy BD, Bertram S, Tai HH, Israel E, Fischer A, Drazen JM, Serhan CN (1993a) Agonist-induced lipoxin A4 generation: detection by a novel lipoxin A4-ELISA. Lipids 28:1047–1053
Levy BD, Romano M, Chapman HA, Reilly JJ, Drazen J, Serhan CN (1993b) Human alveolar macrophages have 15-lipoxygenase and generate 15(S)-hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acid and lipoxins. J Clin Invest 92:1572–1579
Levy BD, Fokin VV, Clark JM, Wakelam MJO, Petasis NA, Serhan CN (1999a) Polyisoprenyl phosphate (PIPP) signaling regulates phospholipase D activity: a “stop” signaling switch for aspirin-triggered lipoxin A4. FASEB J 13:903–911
Levy BD, Gronert K, Clish C, Serhan CN (1999b) Leukotriene and lipoxin biosynthesis. In: Laychock S, Rubin RP (eds) Lipid second messengers. CRC, Boca Raton, p 83
Maddox JF, Serhan CN (1996) Lipoxin A4 and B4 are potent stimuli for human monocyte migration and adhesion: selective inactivation by dehydrogenation and reduction. J Exp Med 183:137–146
Maddox JF, Hachicha M, Takano T, Petasis NA, Fokin VV, Serhan CN (1997) Lipoxin A4 stable analogs are potent mimetics that stimulate human monocytes and THP-1 cells via a G-protein linked lipoxin A4 receptor. J Biol Chem 272:6972–6978
Maddox JF, Colgan SP, Clish CB, Petasis NA, Fokin VV, Serhan CN (1998) Lipoxin B4 regulates human monocyte/neutrophil adherence and motility: design of stable lipoxin B4 analogs with increased biologic activity. FASEB J 12:487–494
Mayadas TN, Mendrick DL, Brady HR, Tang T, Papayianni A, Assmann KJM, Wagner DD, Hynes RO, Cotran RS (1996) Acute passive anti-glomerular basement membrane nephritis in P-selectin-deficient mice. Kidney Int 49:1342–1349
McMahon B, McPhilips F, Fanning A, Brady HR, Godson C (1998) Modulation of mesangial cell MAP kinase activities by leukotriene D4 and lipoxin A4. J Am Soc Nephrol 9:355A
Mitchell S, Harvey K, Fokin VV, Petasis NA, Godson C, Brady HR (1999) Lipoxins stimulate macrophage phagocytosis of apoptotic neutrophils (abstract). FASEB J 13:A557
Murphy PM, Ozcelik T, Kenney RT, Tiffany HL, McDermott D (1992) A structural homologue of the N-formyl peptide receptor: characterization and chromosomal mapping of a peptide chemoattractant receptor gene family. J Biol Chem 267:7637–7643
Nassar GM, Morrow JD, Roberts LJ, II, Lakkis FG, Badr KF (1994) Induction of 15-lipoxygenase by interleukin-13 in human blood monocytes. J Biol Chem 269:27631–27634
Nigam S, Fiore S, Luscinskas FW, Serhan CN (1990) Lipoxin A4 and lipoxin B4 stimulate the release but not the oxygenation of arachidonic acid in human neutrophils: dissociation between lipid remodeling and adhesion. J Cell Physiol 143:512–523
NoMura H, Nielsen BW, Matsushima K (1993) Molecular cloning of cDNAs encoding a LD78 receptor and putative leukocyte chemotactic peptide receptors. Int Immunol 5:1239
Papayianni A, Takata S, Serhan CN, Brady HR (1993) Counter-regulatory actions of leukotrienes (LT) and lipoxins (LX) on P-selectin expression on human endothelial cells and neutrophil-endothelial cell adhesion (abstract). J Am Soc Nephrol 4:627
Papayianni A, Serhan CN, Phillips ML, Rennke HG, Brady HR (1995) Transcellular biosynthesis of lipoxin A4 during adhesion of platelets and neutrophils in experimental immune complex glomerulonephritis. Kidney Int 47:1295–1302
Papayianni A, Serhan CN, Brady HR (1996) Lipoxin A4 and B4 inhibit leukotriene-stimulated interactions of human neutrophils and endothelial cells. J Immunol 156:2264–2272
Perez HD, Holmes R, Kelly E, McClary J, Andrews WH (1992) Cloning of a cDNA encoding a receptor related to the formyl peptide receptor of human neutrophils. Gene 118:303–304
Raud J, Palmertz U, Dahlén SE, Hedqvist P (1991) Lipoxins inhibit microvascular inflammatory actions of leukotriene B4. Adv Exp Med Biol 314:185–192
Romano M, Maddox JF, Serhan CN (1996) Activation of human monocytes and the acute monocytic leukemia cell line (THP-1) by lipoxins involves unique signaling pathways for lipoxin A4 versus lipoxin B4. J Immunol 157:2149–2154
Rowley AF, Lloyd-Evans P, Barrow SE, Serhan CN (1994) Lipoxin biosynthesis by trout macrophages involves the formation of epoxide intermediates. Biochemistry 33:856–863
Scalia R, Gefen J, Petasis NA, Serhan CN, Lefer AM (1997) Lipoxin A4 stable analogs inhibit leukocyte rolling and adherence in the rat mesenteric microvasculature: role of P-selectin. Proc Natl Acad Sci U S A 94:9967–9972
Serhan CN (1994) Lipoxin biosynthesis and its impact in inflammatory and vascular events. Biochim Biophys Acta 1212:1–25
Serhan CN (1997) Lipoxins and novel aspirin-triggered 15-epi-lipoxins (ATL): a jungle of cell-cell interactions or a therapeutic opportunity? Prostaglandins 53:107–137
Serhan CN, Hamberg M, Samuelsson B (1984) Lipoxins: novel series of biologically active compounds formed from arachidonic acid in human leukocytes. Proc Natl Acad Sci U S A 81:5335–5339
Serhan CN, Hirsch U, Palmblad J, Samuelsson B (1987) Formation of lipoxin A by granulocytes from eosinophilic donors. FEBS Lett 217:242–246
Serhan CN, Fiore S, Brezinski DA, Lynch S (1993) Lipoxin A4 metabolism by differentiated HL-60 cells and human monocytes: conversion to novel 15oxo and dihydro products. Biochemistry 32:6313–6319
Serhan CN, Maddox JF, Petasis NA, Akritopoulou-Zanze I, Papayianni A, Brady HR, Colgan SP, Madara JL (1995) Design of lipoxin A4 stable ana- logs that block transmigration and adhesion of human neutrophils. Biochemistry 34:14609–14615
Serhan CN, Haeggström JZ, Leslie CC (1996) Lipid mediator networks in cell signaling: update and impact of cytokines. FASEB J 10:1147–1158
Serhan CN, Takano T, Gronert K, Chiang N, Clish CB (1999) Lipoxin and aspirin-triggered 15-epi-lipoxin cellular interactions: anti-inflammatory lipid mediators. Clin Chem Lab Med 37:299–309
Shen J, Herderick E, Cornhill JF, Zsigmond E, Kim H-S, Kühn H, Guevara NV, Chan L (1996) Macrophage-mediated 15-lipoxygenase expression protects against atherosclerosis development. J Clin Invest 98:2201–2208
Soyombo O, Spur BW, Lee TH (1994) Effects of lipoxin A4 on chemotaxis and degranulation of human eosinophils stimulated by platelet-activating factor and nN formyl-l-methionyl-l-leucyl-l-phenylalanine. Allergy 49:230–234
Stenke L, Näsman-Glaser B, Edenius C, Samuelsson J, Palmblad J, Lindgren JA (1990) Lipoxygenase products in myeloproliferative disorders: increased leukotriene C4 and decreased lipoxin formation in chronic myeloid leukemia. Adv Prostaglandin Thromboxane Leukot Res 21B:883–886
Stenke L, Edenius C, Samuelsson J, Lindgren JA (1991a) Deficient lipoxin synthesis: a novel platelet dysfunction in myeloproliferative disorders with special reference to blastic crisis of chronic myelogenous leukemia. Blood 78:2989–2995
Stenke L, Mansour M, Edenius C, Reizenstein P, Lindgren JA (1991b) Formation and proliferative effects of lipoxins in human bone marrow. Biochem Biophys Res Commun 180:255–261
Stenke L, Reizenstein P, Lindgren JA (1994) Leukotrienes and lipoxins—new potential performers in the regulation of human myelopoiesis. Leuk Res 18:727–732
Takano T, Fiore S, Maddox JF, Brady HR, Petasis NA, Serhan CN (1997) Aspirin-triggered 15-epi-lipoxin A4 and LXA4 stable analogs are potent inhibitors of acute inflammation: Evidence for anti-inflammatory receptors. J Exp Med 185:1693–1704
Takano T, Clish CB, Gronert K, Petasis N, Serhan CN (1998) Neutrophil-mediated changes in vascular permeability are inhibited by topical application of aspirin-triggered 15-epi-lipoxin A4 and novel lipoxin B4 stable analogues. J Clin Invest 101:819–826
Tamaoki J, Tagaya E, Yamawaki I, Konno K (1995) Lipoxin A4 inhibits cholinergic neurotransmission through nitric oxide generation in the rabbit trachea. Eur J Pharmacol 287:233–238
Thomas E, Leroux JL, Blotman F, Chavis C (1995) Conversion of endogenous arachidonic acid to 5,15-diHETE and lipoxins by polymorphonuclear cells from patients with rheumatoid arthritis. Inflamm Res 44:121–124
Toh H, Ichikawa A, Narumiya S (1995) Molecular evolution of receptors for eicosanoids. FEBS Lett 361:17–21
Weissmann G (1993) Prostaglandins as modulators rather than mediators of inflammation. J Lipid Mediat Cell Signal 6:275–286
Weissmann G, Smolen JE, Korchak HM (1980) Release of inflammatory mediators from stimulated neutrophils. N Engl J Med 303:27–34
Wikstrosm-Jonsson E (1998). Functional characterization of receptors for cysteinyl leukotrienes in muscle (doctoral thesis). Karolinka Institute, Stockholm
Ye RD, Cavanagh SL, Quehenberger O, Prossnitz ER, Cocrane C (1992) Isolation of a cDNA that encodes a novel granulocyte N-formyl peptide receptor. Biochem Biophys Res Commun 184:582–589
Yokomizo T, Izumi T, Chang K, Takuwa T, Shimizu T (1997) A G-proteincoupled receptor for leukotriene B4 that mediates chemotaxis. Nature 387:620–624
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2000 Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
Serhan, C.N., Levy, B.D., Clish, C.B., Gronert, K., Chiang, N. (2000). Lipoxins, Aspirin-Triggered 15-epi-Lipoxin Stable Analogs and Their Receptors in Anti-Inflammation: A Window for Therapeutic Opportunity. In: Serhan, C.N., Perez, H.D. (eds) Advances in Eicosanoid Research. Ernst Schering Research Foundation Workshop, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-04047-8_8
Download citation
DOI: https://doi.org/10.1007/978-3-662-04047-8_8
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-04049-2
Online ISBN: 978-3-662-04047-8
eBook Packages: Springer Book Archive