Atypical sphingosine-1-phosphate metabolites-biological implications of alkyl chain length.

Chain lengths Myristoyl CoA Palmitoyl CoA Serine palmitoyl transferase Sphingolipids Sphingosine-1-phosphate (S1P) Stearoyl CoA

Journal

Pflugers Archiv : European journal of physiology
ISSN: 1432-2013
Titre abrégé: Pflugers Arch
Pays: Germany
ID NLM: 0154720

Informations de publication

Date de publication:
19 Sep 2024
Historique:
received: 04 09 2024
accepted: 06 09 2024
revised: 04 09 2024
medline: 20 9 2024
pubmed: 20 9 2024
entrez: 19 9 2024
Statut: aheadofprint

Résumé

Sphingosine-1-phosphate (S1P) is a bioactive lipid signaling molecule with pleiotropic implications by both auto- and paracrine signaling. Signaling occurs by engaging five G protein-coupled receptors (S1P

Identifiants

pubmed: 39297971
doi: 10.1007/s00424-024-03018-8
pii: 10.1007/s00424-024-03018-8
doi:

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Subventions

Organisme : Deutsche Forschungsgemeinschaft
ID : SFB1039
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB1039
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB1039
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB1039
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB1039

Informations de copyright

© 2024. The Author(s).

Références

A treatise on the chemical constitution of the brain : based throughout upon original researches / by J. L. W. Thudichum. In: Wellcome Collection. https://wellcomecollection.org/works/zcf2rr7p . Accessed 27 Aug 2024
Allende ML, Yamashita T, Proia RL (2003) G-protein-coupled receptor S1P1 acts within endothelial cells to regulate vascular maturation. Blood 102:3665–3667. https://doi.org/10.1182/blood-2003-02-0460
doi: 10.1182/blood-2003-02-0460 pubmed: 12869509
Blaho VA, Hla T (2014) An update on the biology of sphingosine 1-phosphate receptors. J Lipid Res 55:1596–1608. https://doi.org/10.1194/jlr.R046300
doi: 10.1194/jlr.R046300 pubmed: 24459205 pmcid: 4109755
Borup A, Donkin I, Boon MR, Frydland M, Martinez-Tellez B, Loft A, Keller SH, Kjaer A, Kjaergaard J, Hassager C, Barrès R, Rensen PCN, Christoffersen C (2022) Association of apolipoprotein M and sphingosine-1-phosphate with brown adipose tissue after cold exposure in humans. Sci Rep 12:18753. https://doi.org/10.1038/s41598-022-21938-2
doi: 10.1038/s41598-022-21938-2 pubmed: 36335116 pmcid: 9637161
Brinkmann V, Billich A, Baumruker T, Heining P, Schmouder R, Francis G, Aradhye S, Burtin P (2010) Fingolimod (FTY720): discovery and development of an oral drug to treat multiple sclerosis. Nat Rev Drug Discov 9:883–897. https://doi.org/10.1038/nrd3248
doi: 10.1038/nrd3248 pubmed: 21031003
Byrdwell WC, Perry RH (2007) Liquid chromatography with dual parallel mass spectrometry and 31P nuclear magnetic resonance spectroscopy for analysis of sphingomyelin and dihydrosphingomyelin. II Bovine milk sphingolipids. J Chromatogr A 1146:164–185. https://doi.org/10.1016/j.chroma.2007.01.108
doi: 10.1016/j.chroma.2007.01.108 pubmed: 17303148
Carter HE, Glick FJ, Norris WP, Phillips GE (1947) Biochemistry of the sphingolipides: III. Structure of sphingosine. J Biol Chem 170:285–294. https://doi.org/10.1016/S0021-9258(17)34955-4
doi: 10.1016/S0021-9258(17)34955-4
Cartier A, Hla T (2019) Sphingosine 1-phosphate: lipid signaling in pathology and therapy. Science 366:eaar5551. https://doi.org/10.1126/science.aar5551
doi: 10.1126/science.aar5551 pubmed: 31624181 pmcid: 7661103
Chigorno V, Valsecchi M, Sonnino S (1994) Biosynthesis of gangliosides containing C18:1 and C20:1 [3-14C]sphingosine after administrating [1-14C]palmitic acid and [1-14C]stearic acid to rat cerebellar granule cells in culture. Eur J Biochem 221:1095–1101. https://doi.org/10.1111/j.1432-1033.1994.tb18829.x
doi: 10.1111/j.1432-1033.1994.tb18829.x pubmed: 8181467
Chua XY, Chai YL, Chew WS, Chong JR, Ang HL, Xiang P, Camara K, Howell AR, Torta F, Wenk MR, Hilal S, Venketasubramanian N, Chen CP, Herr DR, Lai MKP (2020) Immunomodulatory sphingosine-1-phosphates as plasma biomarkers of Alzheimer’s disease and vascular cognitive impairment. Alzheimers Res Ther 12:122. https://doi.org/10.1186/s13195-020-00694-3
doi: 10.1186/s13195-020-00694-3 pubmed: 32998767 pmcid: 7528375
Chun J, Giovannoni G, Hunter SF (2021) Sphingosine 1-phosphate receptor modulator therapy for multiple sclerosis: differential downstream receptor signalling and clinical profile effects. Drugs 81:207–231. https://doi.org/10.1007/s40265-020-01431-8
doi: 10.1007/s40265-020-01431-8 pubmed: 33289881
Cuvillier O, Pirianov G, Kleuser B, Vanek PG, Coso OA, Gutkind JS, Spiegel S (1996) Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature 381:800–803. https://doi.org/10.1038/381800a0
doi: 10.1038/381800a0 pubmed: 8657285
Davis D, Kannan M, Wattenberg B (2018) Orm/ORMDL proteins: gate guardians and master regulators. Adv Biol Regul 70:3–18. https://doi.org/10.1016/j.jbior.2018.08.002
doi: 10.1016/j.jbior.2018.08.002 pubmed: 30193828 pmcid: 6251742
Davis DL, Mahawar U, Pope VS, Allegood J, Sato-Bigbee C, Wattenberg BW (2020) Dynamics of sphingolipids and the serine palmitoyltransferase complex in rat oligodendrocytes during myelination. J Lipid Res 61:505–522. https://doi.org/10.1194/jlr.RA120000627
doi: 10.1194/jlr.RA120000627 pubmed: 32041816 pmcid: 7112141
van Echten G, Birk R, Brenner-Weiss G, Schmidt RR, Sandhoff K (1990) Modulation of sphingolipid biosynthesis in primary cultured neurons by long chain bases. J Biol Chem 265:9333–9339
doi: 10.1016/S0021-9258(19)38853-2 pubmed: 2111818
Forrest M, Sun S-Y, Hajdu R, Bergstrom J, Card D, Doherty G, Hale J, Keohane C, Meyers C, Milligan J, Mills S, Nomura N, Rosen H, Rosenbach M, Shei G-J, Singer II, Tian M, West S, White V, Xie J, Proia RL, Mandala S (2004) Immune cell regulation and cardiovascular effects of sphingosine 1-phosphate receptor agonists in rodents are mediated via distinct receptor subtypes. J Pharmacol Exp Ther 309:758–768. https://doi.org/10.1124/jpet.103.062828
doi: 10.1124/jpet.103.062828 pubmed: 14747617
Glueck M, Koch A, Brunkhorst R, Ferreiros Bouzas N, Trautmann S, Schaefer L, Pfeilschifter W, Pfeilschifter J, Vutukuri R (2022) The atypical sphingosine 1-phosphate variant, d16:1 S1P, mediates CTGF induction via S1P2 activation in renal cell carcinoma. FEBS J 289:5670–5681. https://doi.org/10.1111/febs.16446
doi: 10.1111/febs.16446 pubmed: 35320610
Guo Z, Valenzuela Ripoll C, Picataggi A, Rawnsley DR, Ozcan M, Chirinos JA, Chendamarai E, Girardi A, Riehl T, Evie H, Diab A, Kovacs A, Hyrc K, Ma X, Asnani A, Shewale SV, Scherrer-Crosbie M, Cowart LA, Parks JS, Zhao L, Gordon D, Ramirez-Valle F, Margulies KB, Cappola TP, Desai AA, Pedersen LN, Bergom C, Stitziel NO, Rettig MP, DiPersio JF, Hajny S, Christoffersen C, Diwan A, Javaheri A (2023) Apolipoprotein M attenuates anthracycline cardiotoxicity and lysosomal injury. JACC Basic Transl Sci 8:340–355. https://doi.org/10.1016/j.jacbts.2022.09.010
doi: 10.1016/j.jacbts.2022.09.010 pubmed: 37034289 pmcid: 10077122
Hajri T, Khosla P, Pronczuk A, Hayes KC (1998) Myristic acid-rich fat raises plasma LDL by stimulating LDL production without affecting fractional clearance in gerbils fed a cholesterol-free diet. J Nutr 128:477–484. https://doi.org/10.1093/jn/128.3.477
doi: 10.1093/jn/128.3.477 pubmed: 9482752
Han G, Gupta SD, Gable K, Niranjanakumari S, Moitra P, Eichler F, Brown RH, Harmon JM, Dunn TM (2009) Identification of small subunits of mammalian serine palmitoyltransferase that confer distinct acyl-CoA substrate specificities. Proc Natl Acad Sci U S A 106:8186–8191. https://doi.org/10.1073/pnas.0811269106
doi: 10.1073/pnas.0811269106 pubmed: 19416851 pmcid: 2688822
Hannun YA, Obeid LM (2008) Principles of bioactive lipid signalling: lessons from sphingolipids. Nat Rev Mol Cell Biol 9:139–150. https://doi.org/10.1038/nrm2329
doi: 10.1038/nrm2329 pubmed: 18216770
Hannun YA, Obeid LM (2011) Many ceramides. J Biol Chem 286:27855–27862. https://doi.org/10.1074/jbc.R111.254359
doi: 10.1074/jbc.R111.254359 pubmed: 21693702 pmcid: 3151029
Harrison PJ, Dunn TM, Campopiano DJ (2018) Sphingolipid biosynthesis in man and microbes. Nat Prod Rep 35:921–954. https://doi.org/10.1039/c8np00019k
doi: 10.1039/c8np00019k pubmed: 29863195 pmcid: 6148460
Hirahara Y, Wakabayashi T, Mori T, Koike T, Yao I, Tsuda M, Honke K, Gotoh H, Ono K, Yamada H (2017) Sulfatide species with various fatty acid chains in oligodendrocytes at different developmental stages determined by imaging mass spectrometry. J Neurochem 140:435–450. https://doi.org/10.1111/jnc.13897
doi: 10.1111/jnc.13897 pubmed: 27861899
Hla T, Lee M-J, Ancellin N, Paik JH, Kluk MJ (2001) Lysophospholipids–receptor revelations. Science 294:1875–1878. https://doi.org/10.1126/science.1065323
doi: 10.1126/science.1065323 pubmed: 11729304
Holland WL, Brozinick JT, Wang L-P, Hawkins ED, Sargent KM, Liu Y, Narra K, Hoehn KL, Knotts TA, Siesky A, Nelson DH, Karathanasis SK, Fontenot GK, Birnbaum MJ, Summers SA (2007) Inhibition of ceramide synthesis ameliorates glucocorticoid-, saturated-fat-, and obesity-induced insulin resistance. Cell Metab 5:167–179. https://doi.org/10.1016/j.cmet.2007.01.002
doi: 10.1016/j.cmet.2007.01.002 pubmed: 17339025
Hornemann T, Penno A, Rütti MF, Ernst D, Kivrak-Pfiffner F, Rohrer L, von Eckardstein A (2009) The SPTLC3 subunit of serine palmitoyltransferase generates short chain sphingoid bases. J Biol Chem 284:26322–26330. https://doi.org/10.1074/jbc.M109.023192
doi: 10.1074/jbc.M109.023192 pubmed: 19648650 pmcid: 2785320
Huwiler A, Kolter T, Pfeilschifter J, Sandhoff K (2000) Physiology and pathophysiology of sphingolipid metabolism and signaling. Biochim Biophys Acta 1485:63–99. https://doi.org/10.1016/s1388-1981(00)00042-1
doi: 10.1016/s1388-1981(00)00042-1 pubmed: 10832090
Huwiler A, Pfeilschifter J (2018) Sphingolipid signaling in renal fibrosis. Matrix Biol 68–69:230–247. https://doi.org/10.1016/j.matbio.2018.01.006
doi: 10.1016/j.matbio.2018.01.006 pubmed: 29343457
Jung B, Obinata H, Galvani S, Mendelson K, Ding B, Skoura A, Kinzel B, Brinkmann V, Rafii S, Evans T, Hla T (2012) Flow-regulated endothelial S1P receptor-1 signaling sustains vascular development. Dev Cell 23:600–610. https://doi.org/10.1016/j.devcel.2012.07.015
doi: 10.1016/j.devcel.2012.07.015 pubmed: 22975328 pmcid: 3443394
Kasumov T, Li L, Li M, Gulshan K, Kirwan JP, Liu X, Previs S, Willard B, Smith JD, McCullough A (2015) Ceramide as a mediator of non-alcoholic fatty liver disease and associated atherosclerosis. PLoS ONE 10:e0126910. https://doi.org/10.1371/journal.pone.0126910
doi: 10.1371/journal.pone.0126910 pubmed: 25993337 pmcid: 4439060
Kelly FD, Sinclair AJ, Mann NJ, Turner AH, Abedin L, Li D (2001) A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. Eur J Clin Nutr 55:88–96. https://doi.org/10.1038/sj.ejcn.1601122
doi: 10.1038/sj.ejcn.1601122 pubmed: 11305631
Kitatani K, Cowart LA, Hannun YA (2006) Generation of signaling molecules by de novo sphingolipid synthesis. In: Hirabayashi Y, Igarashi Y, Merrill AH (eds) Sphingolipid biology. Springer Japan, Tokyo, pp 153–165
Kitatani K, Idkowiak-Baldys J, Hannun YA (2008) The sphingolipid salvage pathway in ceramide metabolism and signaling. Cell Signal 20:1010–1018. https://doi.org/10.1016/j.cellsig.2007.12.006
doi: 10.1016/j.cellsig.2007.12.006 pubmed: 18191382
Lucaciu A, Brunkhorst R, Pfeilschifter JM, Pfeilschifter W, Subburayalu J (2020) The S1P–S1PR axis in neurological disorders-insights into current and future therapeutic perspectives. Cells 9:1515. https://doi.org/10.3390/cells9061515
doi: 10.3390/cells9061515 pubmed: 32580348 pmcid: 7349054
Lucaciu A, Kuhn H, Trautmann S, Ferreirós N, Steinmetz H, Pfeilschifter J, Brunkhorst R, Pfeilschifter W, Subburayalu J, Vutukuri R (2020) A sphingosine 1-phosphate gradient is linked to the cerebral recruitment of T helper and regulatory T helper cells during acute ischemic stroke. Int J Mol Sci 21:6242. https://doi.org/10.3390/ijms21176242
doi: 10.3390/ijms21176242 pubmed: 32872326 pmcid: 7503682
Lucaciu A, Trautmann S, Thomas D, Lachner K, Brunkhorst R, Subburayalu J (2022) Characterization of the sphingolipidome of the peri-infarct tissue during hemorrhagic transformation in a mouse model of cerebral ischemia. J Integr Neurosci 21:161. https://doi.org/10.31083/j.jin2106161
doi: 10.31083/j.jin2106161 pubmed: 36424740
Majhofer-Oreščanin B, Proštenik M (1961) Studies in the sphingolipids series. XXI. C20-sphingosine, a new long-chain base of animal origin. Croat Chem Acta 33:219–228
Merrill AH, van Echten G, Wang E, Sandhoff K (1993) Fumonisin B1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ. J Biol Chem 268:27299–27306
doi: 10.1016/S0021-9258(19)74249-5 pubmed: 8262970
Merrill AH, Schmelz EM, Dillehay DL, Spiegel S, Shayman JA, Schroeder JJ, Riley RT, Voss KA, Wang E (1997) Sphingolipids–the enigmatic lipid class: biochemistry, physiology, and pathophysiology. Toxicol Appl Pharmacol 142:208–225. https://doi.org/10.1006/taap.1996.8029
doi: 10.1006/taap.1996.8029 pubmed: 9007051
Morstein J, Hill RZ, Novak AJE, Feng S, Norman DD, Donthamsetti PC, Frank JA, Harayama T, Williams BM, Parrill AL, Tigyi GJ, Riezman H, Isacoff EY, Bautista DM, Trauner D (2019) Optical control of sphingosine-1-phosphate formation and function. Nat Chem Biol 15:623–631. https://doi.org/10.1038/s41589-019-0269-7
doi: 10.1038/s41589-019-0269-7 pubmed: 31036923 pmcid: 7428055
Muralidharan S, Shimobayashi M, Ji S, Burla B, Hall MN, Wenk MR, Torta F (2021) A reference map of sphingolipids in murine tissues. Cell Rep 35:109250. https://doi.org/10.1016/j.celrep.2021.109250
doi: 10.1016/j.celrep.2021.109250 pubmed: 34133933
Nagree MS, Rybova J, Kleynerman A, Ahrenhoerster CJ, Saville JT, Xu T, Bachochin M, McKillop WM, Lawlor MW, Pshezhetsky AV, Isaeva O, Budde MD, Fuller M, Medin JA (2023) Spinal muscular atrophy-like phenotype in a mouse model of acid ceramidase deficiency. Commun Biol 6:560. https://doi.org/10.1038/s42003-023-04932-w
doi: 10.1038/s42003-023-04932-w pubmed: 37231125 pmcid: 10212955
Nieto FL, Pescio LG, Favale NO, Adamo AM, Sterin-Speziale NB (2008) Sphingolipid metabolism is a crucial determinant of cellular fate in nonstimulated proliferating Madin-Darby canine kidney (MDCK) cells. J Biol Chem 283:25682–25691. https://doi.org/10.1074/jbc.M804437200
doi: 10.1074/jbc.M804437200 pubmed: 18625703
Novgorodov SA, Chudakova DA, Wheeler BW, Bielawski J, Kindy MS, Obeid LM, Gudz TI (2011) Developmentally regulated ceramide synthase 6 increases mitochondrial Ca2+ loading capacity and promotes apoptosis. J Biol Chem 286:4644–4658. https://doi.org/10.1074/jbc.M110.164392
doi: 10.1074/jbc.M110.164392 pubmed: 21148554
Olivera A, Allende ML, Proia RL (2013) Shaping the landscape: metabolic regulation of S1P gradients. Biochim Biophys Acta 1831:193–202. https://doi.org/10.1016/j.bbalip.2012.06.007
doi: 10.1016/j.bbalip.2012.06.007 pubmed: 22735358
Olivera A, Spiegel S (1993) Sphingosine-1-phosphate as second messenger in cell proliferation induced by PDGF and FCS mitogens. Nature 365:557–560. https://doi.org/10.1038/365557a0
doi: 10.1038/365557a0 pubmed: 8413613
Osawa Y, Banno Y, Nagaki M, Brenner DA, Naiki T, Nozawa Y, Nakashima S, Moriwaki H (2001) TNF-α-induced sphingosine 1-phosphate inhibits apoptosis through a phosphatidylinositol 3-kinase/Akt pathway in human hepatocytes1. J Immunol 167:173–180. https://doi.org/10.4049/jimmunol.167.1.173
doi: 10.4049/jimmunol.167.1.173 pubmed: 11418646
Othman A, Saely CH, Muendlein A, Vonbank A, Drexel H, von Eckardstein A, Hornemann T (2015) Plasma C20-sphingolipids predict cardiovascular events independently from conventional cardiovascular risk factors in patients undergoing coronary angiography. Atherosclerosis 240:216–221. https://doi.org/10.1016/j.atherosclerosis.2015.03.011
doi: 10.1016/j.atherosclerosis.2015.03.011 pubmed: 25801014
Ottenlinger FM, Mayer CA, Ferreirós N, Schreiber Y, Schwiebs A, Schmidt KG, Ackermann H, Pfeilschifter JM, Radeke HH (2016) Interferon-beta increases plasma ceramides of specific chain length in multiple sclerosis patients, unlike fingolimod or natalizumab. Front Pharmacol 7:412. https://doi.org/10.3389/fphar.2016.00412
doi: 10.3389/fphar.2016.00412 pubmed: 27857690 pmcid: 5093125
Paik JH, Chae S, Lee M-J, Thangada S, Hla T (2001) Sphingosine 1-phosphate-induced endothelial cell migration requires the expression of EDG-1 and EDG-3 receptors and rho-dependent activation of αvβ3- and β1-containing integrins*. J Biol Chem 276:11830–11837. https://doi.org/10.1074/jbc.M009422200
doi: 10.1074/jbc.M009422200 pubmed: 11150298
Pappu R, Schwab SR, Cornelissen I, Pereira JP, Regard JB, Xu Y, Camerer E, Zheng Y-W, Huang Y, Cyster JG, Coughlin SR (2007) Promotion of lymphocyte egress into blood and lymph by distinct sources of sphingosine-1-phosphate. Science 316:295–298. https://doi.org/10.1126/science.1139221
doi: 10.1126/science.1139221 pubmed: 17363629
Park T-S, Panek RL, Mueller SB, Hanselman JC, Rosebury WS, Robertson AW, Kindt EK, Homan R, Karathanasis SK, Rekhter MD (2004) Inhibition of sphingomyelin synthesis reduces atherogenesis in apolipoprotein E-knockout mice. Circulation 110:3465–3471. https://doi.org/10.1161/01.CIR.0000148370.60535.22
doi: 10.1161/01.CIR.0000148370.60535.22 pubmed: 15545514
Pébay A, Toutant M, Prémont J, Calvo CF, Venance L, Cordier J, Glowinski J, Tencé M (2001) Sphingosine-1-phosphate induces proliferation of astrocytes: regulation by intracellular signalling cascades. Eur J Neurosci 13:2067–2076
doi: 10.1046/j.0953-816x.2001.01585.x pubmed: 11467306
Proia RL, Hla T (2015) Emerging biology of sphingosine-1-phosphate: its role in pathogenesis and therapy. J Clin Invest 125:1379–1387. https://doi.org/10.1172/JCI76369
doi: 10.1172/JCI76369 pubmed: 25831442 pmcid: 4409021
Raman MCC, Johnson KA, Yard BA, Lowther J, Carter LG, Naismith JH, Campopiano DJ (2009) The external aldimine form of serine palmitoyltransferase: structural, kinetic, and spectroscopic analysis of the wild-type enzyme and HSAN1 mutant mimics. J Biol Chem 284:17328–17339. https://doi.org/10.1074/jbc.M109.008680
doi: 10.1074/jbc.M109.008680 pubmed: 19376777 pmcid: 2719368
Riboni L, Tettamanti G, Viani P (2002) Ceramide in primary astrocytes from cerebellum: metabolism and role in cell proliferation. Cerebellum 1:129–135. https://doi.org/10.1080/147342202753671268
doi: 10.1080/147342202753671268 pubmed: 12882362
Rosenberg A, Stern N (1966) Changes in sphingosine and fatty acid components of the gangliosides in developing rat and human brain. J Lipid Res 7:122–131
doi: 10.1016/S0022-2275(20)39594-8 pubmed: 5900210
Russo SB, Tidhar R, Futerman AH, Cowart LA (2013) Myristate-derived d16:0 sphingolipids constitute a cardiac sphingolipid pool with distinct synthetic routes and functional properties. J Biol Chem 288:13397–13409. https://doi.org/10.1074/jbc.M112.428185
doi: 10.1074/jbc.M112.428185 pubmed: 23530041 pmcid: 3650378
Saito M, Chakraborty G, Hegde M, Ohsie J, Paik S-M, Vadasz C, Saito M (2010) Involvement of ceramide in ethanol-induced apoptotic neurodegeneration in the neonatal mouse brain. J Neurochem 115:168–177. https://doi.org/10.1111/j.1471-4159.2010.06913.x
doi: 10.1111/j.1471-4159.2010.06913.x pubmed: 20663015 pmcid: 2939968
Sambasivarao K, McCluer RH (1964) Lipid components of gangliosides. J Lipid Res 5:103–108. https://doi.org/10.1016/S0022-2275(20)40268-8
doi: 10.1016/S0022-2275(20)40268-8 pubmed: 14173314
Schiffmann S, Ziebell S, Sandner J, Birod K, Deckmann K, Hartmann D, Rode S, Schmidt H, Angioni C, Geisslinger G, Grösch S (2010) Activation of ceramide synthase 6 by celecoxib leads to a selective induction of C16:0-ceramide. Biochem Pharmacol 80:1632–1640. https://doi.org/10.1016/j.bcp.2010.08.012
doi: 10.1016/j.bcp.2010.08.012 pubmed: 20735991
Schwab SR, Cyster JG (2007) Finding a way out: lymphocyte egress from lymphoid organs. Nat Immunol 8:1295–1301. https://doi.org/10.1038/ni1545
doi: 10.1038/ni1545 pubmed: 18026082
Schwalm S, Pfeilschifter J, Huwiler A (2013) Sphingosine-1-phosphate: a Janus-faced mediator of fibrotic diseases. Biochim Biophys Acta 1831:239–250. https://doi.org/10.1016/j.bbalip.2012.07.022
doi: 10.1016/j.bbalip.2012.07.022 pubmed: 22889995
Schwarz HP, Kostyk I, Marmolejo A, Sarappa C (1967) Long-chain bases of brain and spinal cord of rabbits. J Neurochem 14:91–97. https://doi.org/10.1111/j.1471-4159.1967.tb09497.x
doi: 10.1111/j.1471-4159.1967.tb09497.x pubmed: 6018082
Siow DL, Wattenberg BW (2012) Mammalian ORMDL proteins mediate the feedback response in ceramide biosynthesis. J Biol Chem 287:40198–40204. https://doi.org/10.1074/jbc.C112.404012
doi: 10.1074/jbc.C112.404012 pubmed: 23066021 pmcid: 3504734
Soliven B, Miron V, Chun J (2011) The neurobiology of sphingosine 1-phosphate signaling and sphingosine 1-phosphate receptor modulators. Neurology 76:S9-14. https://doi.org/10.1212/WNL.0b013e31820d9507
doi: 10.1212/WNL.0b013e31820d9507 pubmed: 21339490
Sonnino S, Chigorno V (2000) Ganglioside molecular species containing C18- and C20-sphingosine in mammalian nervous tissues and neuronal cell cultures. Biochim Biophys Acta 1469:63–77. https://doi.org/10.1016/s0005-2736(00)00210-8
doi: 10.1016/s0005-2736(00)00210-8 pubmed: 10998569
Stanacev NZ, Chargaff E (1962) Icosisphingosine, a long-chain base constituent of mucolipids. Biochim Biophys Acta 59:733–734. https://doi.org/10.1016/0006-3002(62)90662-5
doi: 10.1016/0006-3002(62)90662-5 pubmed: 13916182
Stepanovska B, Huwiler A (2020) Targeting the S1P receptor signaling pathways as a promising approach for treatment of autoimmune and inflammatory diseases. Pharmacol Res 154:104170. https://doi.org/10.1016/j.phrs.2019.02.009
doi: 10.1016/j.phrs.2019.02.009 pubmed: 30776422
Sternstein C, Schlegel J, Sauer M, Seibel J (2023) Bioorthogonal azido-S1P works as substrate for S1PR1. J Lipid Res 64:100311. https://doi.org/10.1016/j.jlr.2022.100311
doi: 10.1016/j.jlr.2022.100311 pubmed: 36370806
Swendeman SL, Xiong Y, Cantalupo A, Yuan H, Burg N, Hisano Y, Cartier A, Liu CH, Engelbrecht E, Blaho V, Zhang Y, Yanagida K, Galvani S, Obinata H, Salmon JE, Sanchez T, Di Lorenzo A, Hla T (2017) An engineered S1P chaperone attenuates hypertension and ischemic injury. Sci Signal 10:eaal2722. https://doi.org/10.1126/scisignal.aal2722
doi: 10.1126/scisignal.aal2722 pubmed: 28811382 pmcid: 5680089
Troupiotis-Tsaïlaki A, Zachmann J, González-Gil I, Gonzalez A, Ortega-Gutiérrez S, López-Rodríguez ML, Pardo L, Govaerts C (2017) Ligand chain length drives activation of lipid G protein-coupled receptors. Sci Rep 7:2020. https://doi.org/10.1038/s41598-017-02104-5
doi: 10.1038/s41598-017-02104-5 pubmed: 28515494 pmcid: 5435731
Tsai H-C, Han MH (2016) Sphingosine-1-phosphate (S1P) and S1P signaling pathway: therapeutic targets in autoimmunity and inflammation. Drugs 76:1067–1079. https://doi.org/10.1007/s40265-016-0603-2
doi: 10.1007/s40265-016-0603-2 pubmed: 27318702
Venkataraman K, Lee Y-M, Michaud J, Thangada S, Ai Y, Bonkovsky HL, Parikh NS, Habrukowich C, Hla T (2008) Vascular endothelium as a contributor of plasma sphingosine 1-phosphate. Circ Res 102:669–676. https://doi.org/10.1161/CIRCRESAHA.107.165845
doi: 10.1161/CIRCRESAHA.107.165845 pubmed: 18258856 pmcid: 2659392
Vutukuri R, Brunkhorst R, Kestner R-I, Hansen L, Bouzas NF, Pfeilschifter J, Devraj K, Pfeilschifter W (2018) Alteration of sphingolipid metabolism as a putative mechanism underlying LPS-induced BBB disruption. J Neurochem 144:172–185. https://doi.org/10.1111/jnc.14236
doi: 10.1111/jnc.14236 pubmed: 29023711
Vutukuri R, Koch A, Trautmann S, Schreiber Y, Thomas D, Mayser F, Meyer Zu Heringdorf D, Pfeilschifter J, Pfeilschifter W, Brunkhorst R (2020) S1P d20:1, an endogenous modulator of S1P d18:1/S1P2 -dependent signaling. FASEB J 34:3932–3942. https://doi.org/10.1096/fj.201902391R
doi: 10.1096/fj.201902391R pubmed: 31944406
Wang W, Xiang P, Chew WS, Torta F, Bandla A, Lopez V, Seow WL, Lam BWS, Chang JK, Wong P, Chayaburakul K, Ong W-Y, Wenk MR, Sundar R, Herr DR (2020) Activation of sphingosine 1-phosphate receptor 2 attenuates chemotherapy-induced neuropathy. J Biol Chem 295:1143–1152. https://doi.org/10.1074/jbc.RA119.011699
doi: 10.1074/jbc.RA119.011699 pubmed: 31882542
Wheeler D, Bandaru VVR, Calabresi PA, Nath A, Haughey NJ (2008) A defect of sphingolipid metabolism modifies the properties of normal appearing white matter in multiple sclerosis. Brain 131:3092–3102. https://doi.org/10.1093/brain/awn190
doi: 10.1093/brain/awn190 pubmed: 18772223 pmcid: 2577809
Wu Y-P, Mizugishi K, Bektas M, Sandhoff R, Proia RL (2008) Sphingosine kinase 1/S1P receptor signaling axis controls glial proliferation in mice with Sandhoff disease. Hum Mol Genet 17:2257–2264. https://doi.org/10.1093/hmg/ddn126
doi: 10.1093/hmg/ddn126 pubmed: 18424450 pmcid: 2548282
Yavin E, Menkes JH (1973) Glyceride metabolism in cultured cells dissociated from rat cerebral cortex. J Neurochem 21:901–912. https://doi.org/10.1111/j.1471-4159.1973.tb07535.x
doi: 10.1111/j.1471-4159.1973.tb07535.x pubmed: 4356840
Zhang G, Yang L, Kim GS, Ryan K, Lu S, O’Donnell RK, Spokes K, Shapiro N, Aird WC, Kluk MJ, Yano K, Sanchez T (2013) Critical role of sphingosine-1-phosphate receptor 2 (S1PR2) in acute vascular inflammation. Blood 122:443–455. https://doi.org/10.1182/blood-2012-11-467191
doi: 10.1182/blood-2012-11-467191 pubmed: 23723450 pmcid: 3716205
Zhao L, Spassieva S, Gable K, Gupta SD, Shi L-Y, Wang J, Bielawski J, Hicks WL, Krebs MP, Naggert J, Hannun YA, Dunn TM, Nishina PM (2015) Elevation of 20-carbon long chain bases due to a mutation in serine palmitoyltransferase small subunit b results in neurodegeneration. Proc Natl Acad Sci U S A 112:12962–12967. https://doi.org/10.1073/pnas.1516733112
doi: 10.1073/pnas.1516733112 pubmed: 26438849 pmcid: 4620873

Auteurs

Melanie Glueck (M)

Institute of General Pharmacology and Toxicology, Pharmazentrum Frankfurt, Goethe University, Frankfurt am Main, 60596, Frankfurt, Germany.
Institute for Transfusion Medicine and Immunohaematology, German Red Cross Blood Donor Service Baden-Württemberg-Hessen, Goethe University Hospital, 60528, Frankfurt Am Main, Germany.

Alexandra Lucaciu (A)

Institute of General Pharmacology and Toxicology, Pharmazentrum Frankfurt, Goethe University, Frankfurt am Main, 60596, Frankfurt, Germany.
Department of Neurology, University Hospital Frankfurt, Frankfurt, Goethe University, Frankfurt am Main, 60528, Frankfurt, Germany.

Julien Subburayalu (J)

Department of Internal Medicine, University Hospital Carl Gustav Carus TU Dresden, Fetscherstraße 74, 01307, Dresden, Saxony, Germany.
Center of Regenerative Therapies Dresden, TU Dresden, Fetscherstraße 74, 01307, Dresden, Saxony, Germany.

Roxane Isabelle Kestner (RI)

Institute of General Pharmacology and Toxicology, Pharmazentrum Frankfurt, Goethe University, Frankfurt am Main, 60596, Frankfurt, Germany.
Department of Neurology, University Hospital Frankfurt, Frankfurt, Goethe University, Frankfurt am Main, 60528, Frankfurt, Germany.

Waltraud Pfeilschifter (W)

Institute of General Pharmacology and Toxicology, Pharmazentrum Frankfurt, Goethe University, Frankfurt am Main, 60596, Frankfurt, Germany.
Department of Neurology and Clinical Neurophysiology, Städtisches Klinikum Lüneburg, 21339, Lüneburg, Germany.

Rajkumar Vutukuri (R)

Institute of General Pharmacology and Toxicology, Pharmazentrum Frankfurt, Goethe University, Frankfurt am Main, 60596, Frankfurt, Germany. vutukuri@med.uni-frankfurt.de.

Josef Pfeilschifter (J)

Institute of General Pharmacology and Toxicology, Pharmazentrum Frankfurt, Goethe University, Frankfurt am Main, 60596, Frankfurt, Germany. pfeilschifter@em.uni-frankfurt.de.

Classifications MeSH