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Chemical Compound Review

sphingosine     (E,2S,3R)-2-aminooctadec-4- ene-1,3-diol

Synonyms: Sphingoid, Sphingenine, cerebroside, D-Sphingosine, AC1NQWWW, ...
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Disease relevance of sphingosine


High impact information on sphingosine

  • Alteration of the 4-sphingenine scaffolds of ceramides in keratinocyte-specific Arnt-deficient mice affects skin barrier function [6].
  • Mammalian S1P phosphatase (SPP-1), which degrades S1P to terminate its actions, was recently cloned based on homology to a lipid phosphohydrolase that regulates the levels of phosphorylated sphingoid bases in yeast [7].
  • In a screen to detect proteins involved in ubiquitin-dependent receptor internalization, we identified the sphingoid base-regulated serine-threonine kinase Ypk1 [8].
  • These results suggest that Pkh1/2p kinases are part of a sphingoid base-mediated signaling pathway that is required for the internalization step of endocytosis [9].
  • We show that overexpression of either one of the two kinases Pkh1p or Pkh2p, that are homologous to mammalian 3-phosphoinositide-dependent kinase-1 (PDK1), can specifically suppress the sphingoid base synthesis requirement for endocytosis [9].

Chemical compound and disease context of sphingosine


Biological context of sphingosine


Anatomical context of sphingosine


Associations of sphingosine with other chemical compounds


Gene context of sphingosine

  • Phosphorylation by Pho85 cyclin-dependent kinase acts as a signal for the down-regulation of the yeast sphingoid long-chain base kinase Lcb4 during the stationary phase [29].
  • Interestingly, cell cycle recovery from the transient arrest was found to be dependent upon the sphingoid base kinases (LCB4, LCB5) [26].
  • Both genes functionally and biochemically complement a yeast sphingosine kinase mutant, express predominantly cytosolic activities, and are capable of phosphorylating a range of endogenous and non-endogenous sphingoid base substrates [30].
  • We observed concentration- and time-dependent activation of PAK1 by sphingosine and several related long chain sphingoid bases but not by ceramides or a variety of other lipids [31].
  • Tsc3p is apparently not required for any essential process besides stimulation of serine palmitoyltransferase at 37 degrees C, since providing sphingoid bases to the growth medium reverses the temperature-sensitive growth phenotype of the tsc3 delta mutant [32].

Analytical, diagnostic and therapeutic context of sphingosine


  1. The transcriptional coactivator FHL2 transmits Rho signals from the cell membrane into the nucleus. Müller, J.M., Metzger, E., Greschik, H., Bosserhoff, A.K., Mercep, L., Buettner, R., Schüle, R. EMBO J. (2002) [Pubmed]
  2. Slm1 and slm2 are novel substrates of the calcineurin phosphatase required for heat stress-induced endocytosis of the yeast uracil permease. Bultynck, G., Heath, V.L., Majeed, A.P., Galan, J.M., Haguenauer-Tsapis, R., Cyert, M.S. Mol. Cell. Biol. (2006) [Pubmed]
  3. Sphingosine-induced apoptosis in rhabdomyosarcoma cell lines is dependent on pre-mitochondrial Bax activation and post-mitochondrial caspases. Phillips, D.C., Martin, S., Doyle, B.T., Houghton, J.A. Cancer Res. (2007) [Pubmed]
  4. Endothelial differentiation gene receptors in pancreatic islets and INS-1 cells. Laychock, S.G., Tian, Y., Sessanna, S.M. Diabetes (2003) [Pubmed]
  5. Retinoblastoma protein dephosphorylation induced by D-erythro-sphingosine. Chao, R., Khan, W., Hannun, Y.A. J. Biol. Chem. (1992) [Pubmed]
  6. Alteration of the 4-sphingenine scaffolds of ceramides in keratinocyte-specific Arnt-deficient mice affects skin barrier function. Takagi, S., Tojo, H., Tomita, S., Sano, S., Itami, S., Hara, M., Inoue, S., Horie, K., Kondoh, G., Hosokawa, K., Gonzalez, F.J., Takeda, J. J. Clin. Invest. (2003) [Pubmed]
  7. Sphingosine-1-phosphate phosphohydrolase in regulation of sphingolipid metabolism and apoptosis. Le Stunff, H., Galve-Roperh, I., Peterson, C., Milstien, S., Spiegel, S. J. Cell Biol. (2002) [Pubmed]
  8. The conserved Pkh-Ypk kinase cascade is required for endocytosis in yeast. deHart, A.K., Schnell, J.D., Allen, D.A., Hicke, L. J. Cell Biol. (2002) [Pubmed]
  9. Sphingoid base signaling via Pkh kinases is required for endocytosis in yeast. Friant, S., Lombardi, R., Schmelzle, T., Hall, M.N., Riezman, H. EMBO J. (2001) [Pubmed]
  10. Induction of apoptosis and potentiation of ceramide-mediated cytotoxicity by sphingoid bases in human myeloid leukemia cells. Jarvis, W.D., Fornari, F.A., Traylor, R.S., Martin, H.A., Kramer, L.B., Erukulla, R.K., Bittman, R., Grant, S. J. Biol. Chem. (1996) [Pubmed]
  11. Sphingolipid receptor signaling and function in human bladder carcinoma cells: inhibition of LPA- but enhancement of thrombin-stimulated cell motility. Rümenapp, U., Lümmen, G., Virchow, S., Hanske, J., Meyer zu Heringdorf, D., Jakobs, K.H. Naunyn Schmiedebergs Arch. Pharmacol. (2000) [Pubmed]
  12. Sphinganine causes early activation of JNK and p38 MAPK and inhibition of AKT activation in HT-29 human colon cancer cells. Ahn, E.H., Schroeder, J.J. Anticancer Res. (2006) [Pubmed]
  13. Effects of prostaglandin E2 on amiloride-blockable Na+ channels in a distal nephron cell line (A6). Kokko, K.E., Matsumoto, P.S., Ling, B.N., Eaton, D.C. Am. J. Physiol. (1994) [Pubmed]
  14. Sphingoid bases and ceramide induce apoptosis in HT-29 and HCT-116 human colon cancer cells. Ahn, E.H., Schroeder, J.J. Exp. Biol. Med. (Maywood) (2002) [Pubmed]
  15. Sphingoid base synthesis requirement for endocytosis in Saccharomyces cerevisiae. Zanolari, B., Friant, S., Funato, K., Sütterlin, C., Stevenson, B.J., Riezman, H. EMBO J. (2000) [Pubmed]
  16. Increased protein kinase or decreased PP2A activity bypasses sphingoid base requirement in endocytosis. Friant, S., Zanolari, B., Riezman, H. EMBO J. (2000) [Pubmed]
  17. Molecular cloning and characterization of a lipid phosphohydrolase that degrades sphingosine-1- phosphate and induces cell death. Mandala, S.M., Thornton, R., Galve-Roperh, I., Poulton, S., Peterson, C., Olivera, A., Bergstrom, J., Kurtz, M.B., Spiegel, S. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  18. Induction of apoptosis by sphingoid long-chain bases in Aspergillus nidulans. Cheng, J., Park, T.S., Chio, L.C., Fischl, A.S., Ye, X.S. Mol. Cell. Biol. (2003) [Pubmed]
  19. Ceramide inhibits IgG-dependent phagocytosis in human polymorphonuclear leukocytes. Suchard, S.J., Hinkovska-Galcheva, V., Mansfield, P.J., Boxer, L.A., Shayman, J.A. Blood (1997) [Pubmed]
  20. Disruption of the FATB gene in Arabidopsis demonstrates an essential role of saturated fatty acids in plant growth. Bonaventure, G., Salas, J.J., Pollard, M.R., Ohlrogge, J.B. Plant Cell (2003) [Pubmed]
  21. Sphingoid base synthesis is required for oligomerization and cell surface stability of the yeast plasma membrane ATPase, Pma1. Wang, Q., Chang, A. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  22. Sphingosine-1-phosphate: a platelet-activating sphingolipid released from agonist-stimulated human platelets. Yatomi, Y., Ruan, F., Hakomori, S., Igarashi, Y. Blood (1995) [Pubmed]
  23. Induction and suppression of endothelial cell apoptosis by sphingolipids: a possible in vitro model for cell-cell interactions between platelets and endothelial cells. Hisano, N., Yatomi, Y., Satoh, K., Akimoto, S., Mitsumata, M., Fujino, M.A., Ozaki, Y. Blood (1999) [Pubmed]
  24. A new class of lipid desaturase central to sphingolipid biosynthesis and signalling. Napier, J.A., Michaelson, L.V., Dunn, T.M. Trends Plant Sci. (2002) [Pubmed]
  25. Sphingolipids are essential for the growth of Chinese hamster ovary cells. Restoration of the growth of a mutant defective in sphingoid base biosynthesis by exogenous sphingolipids. Hanada, K., Nishijima, M., Kiso, M., Hasegawa, A., Fujita, S., Ogawa, T., Akamatsu, Y. J. Biol. Chem. (1992) [Pubmed]
  26. Role for de novo sphingoid base biosynthesis in the heat-induced transient cell cycle arrest of Saccharomyces cerevisiae. Jenkins, G.M., Hannun, Y.A. J. Biol. Chem. (2001) [Pubmed]
  27. The sphingoid long chain base phytosphingosine activates AGC-type protein kinases in Saccharomyces cerevisiae including Ypk1, Ypk2, and Sch9. Liu, K., Zhang, X., Lester, R.L., Dickson, R.C. J. Biol. Chem. (2005) [Pubmed]
  28. Ceramide regulates oxidant release in adherent human neutrophils. Nakamura, T., Abe, A., Balazovich, K.J., Wu, D., Suchard, S.J., Boxer, L.A., Shayman, J.A. J. Biol. Chem. (1994) [Pubmed]
  29. Phosphorylation by Pho85 cyclin-dependent kinase acts as a signal for the down-regulation of the yeast sphingoid long-chain base kinase Lcb4 during the stationary phase. Iwaki, S., Kihara, A., Sano, T., Igarashi, Y. J. Biol. Chem. (2005) [Pubmed]
  30. Characterization of the Drosophila sphingosine kinases and requirement for Sk2 in normal reproductive function. Herr, D.R., Fyrst, H., Creason, M.B., Phan, V.H., Saba, J.D., Harris, G.L. J. Biol. Chem. (2004) [Pubmed]
  31. A GTPase-independent mechanism of p21-activated kinase activation. Regulation by sphingosine and other biologically active lipids. Bokoch, G.M., Reilly, A.M., Daniels, R.H., King, C.C., Olivera, A., Spiegel, S., Knaus, U.G. J. Biol. Chem. (1998) [Pubmed]
  32. Mutations in the Lcb2p subunit of serine palmitoyltransferase eliminate the requirement for the TSC3 gene in Saccharomyces cerevisiae. Monaghan, E., Gable, K., Dunn, T. Yeast (2002) [Pubmed]
  33. The immune modulator FTY720 inhibits sphingosine-1-phosphate lyase activity. Bandhuvula, P., Tam, Y.Y., Oskouian, B., Saba, J.D. J. Biol. Chem. (2005) [Pubmed]
  34. Activation of the melastatin-related cation channel TRPM3 [corrected] by D-erythro-sphingosine. Grimm, C., Kraft, R., Schultz, G., Harteneck, C. Mol. Pharmacol. (2005) [Pubmed]
  35. Sphingolipid bases. A revisitation of the O-methyl derivatives of sphingosine. Isolation and characterization of diacetate derivatives, with revised 13C nuclear magnetic resonance assignments for D-erythro-sphingosine. Kisic, A., Tsuda, M., Kulmacz, R.J., Wilson, W.K., Schroepfer, G.J. J. Lipid Res. (1995) [Pubmed]
  36. Free ceramide, sphingomyelin, and glucosylceramide of isolated rat intestinal cells. Bouhours, J.F., Guignard, H. J. Lipid Res. (1979) [Pubmed]
  37. Free sphingosines of human skin include 6-hydroxysphingosine and unusually long-chain dihydrosphingosines. Stewart, M.E., Downing, D.T. J. Invest. Dermatol. (1995) [Pubmed]
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