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Chemical Compound Review

AC1NRD7S     N-[(E,3R)-1,3- dihydroxyoctadec-4-en-2...

Synonyms: SPL, 3036-EP2298776A1, 3036-EP2314574A1
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Disease relevance of ceramide


Psychiatry related information on ceramide


High impact information on ceramide

  • Increased de novo ceramide synthesis triggers apoptosis and is associated with massive cell death during neural tube closure, raising the possibility that neural degeneration in HSN1 is due to ceramide-induced apoptotic cell death [10].
  • These mutations are associated with increased de novo glucosyl ceramide synthesis in lymphoblast cell lines in affected individuals [10].
  • The human specific allele of PapG binds to globoside (GbO4), which consists of the tetrasaccharide GalNAc beta 1-3Gal alpha 1-4Gal beta 1-4Glc linked to ceramide [11].
  • We also found that Pml is essential for induction of programmed cell death by Fas, tumour necrosis factor alpha (TNF), ceramide and type I and II interferons (IFNs) [12].
  • In vitro, low nanomolar concentrations of natural ceramide stimulate KSR to autophosphorylate, and transactivate Raf-1 [13].

Chemical compound and disease context of ceramide


Biological context of ceramide

  • Ceramide synthase mediates daunorubicin-induced apoptosis: an alternative mechanism for generating death signals [18].
  • Daunorubicin-stimulated ceramide elevation, however, did not result from sphingomyelin hydrolysis, but rather from de novo synthesis via activation of the enzyme ceramide synthase [18].
  • Stress is believed to activate sphingomyelinase to generate ceramide, which serves as a second messenger in initiating the apoptotic response [19].
  • Assayed with a natural substrate, n-acetylgalactosaminyl beta 1-4 galactosyl beta 1-4 glucosyl ceramide, which had been isolated from the brain of a patient with Tay--Sachs disease and labeled in the terminal n-acetyl-galactosamine, a value in the heterozygote range was found [20].
  • Phosphorylation of Raf by ceramide-activated protein kinase [21].

Anatomical context of ceramide

  • This truncated C8C8 ceramide was soluble in water (but was still able to cross cell membranes) and was utilized by the Golgi apparatus of living cells to produce water-soluble truncated phospholipids and glycolipids that were then secreted into the medium [22].
  • Using different human epithelial cells and primary fibroblasts, we show here an activation of the phosphatidylcholine-specific phospholipase C (PC-PLC) and acidic sphingomyelinase (ASM) by N. gonorrhoeae, resulting in the release of diacylglycerol and ceramide [23].
  • In the present studies, the anticancer drug daunorubicin also stimulated ceramide elevation and apoptosis in P388 and U937 cells [18].
  • NGF binding to mature oligodendrocytes expressing the p75 neurotrophin receptor, but not trkA, resulted in a sustained increase of intracellular ceramide and c-Jun amino-terminal kinase (JNK) activity, which are thought to participate in a signal transduction pathway leading to cell death [24].
  • Here we report that when mouse intestines were protected against microvascular apoptosis, radiation switched as the dose escalated to a previously unrecognized crypt stem cell target, activating ceramide synthase-mediated apoptosis to initiate intestinal damage [4].

Associations of ceramide with other chemical compounds


Gene context of ceramide


Analytical, diagnostic and therapeutic context of ceramide


  1. Host defense against Pseudomonas aeruginosa requires ceramide-rich membrane rafts. Grassmé, H., Jendrossek, V., Riehle, A., von Kürthy, G., Berger, J., Schwarz, H., Weller, M., Kolesnick, R., Gulbins, E. Nat. Med. (2003) [Pubmed]
  2. Ceramide upregulation causes pulmonary cell apoptosis and emphysema-like disease in mice. Petrache, I., Natarajan, V., Zhen, L., Medler, T.R., Richter, A.T., Cho, C., Hubbard, W.C., Berdyshev, E.V., Tuder, R.M. Nat. Med. (2005) [Pubmed]
  3. PAF-mediated pulmonary edema: a new role for acid sphingomyelinase and ceramide. Göggel, R., Winoto-Morbach, S., Vielhaber, G., Imai, Y., Lindner, K., Brade, L., Brade, H., Ehlers, S., Slutsky, A.S., Schütze, S., Gulbins, E., Uhlig, S. Nat. Med. (2004) [Pubmed]
  4. ATM regulates target switching to escalating doses of radiation in the intestines. Ch'ang, H.J., Maj, J.G., Paris, F., Xing, H.R., Zhang, J., Truman, J.P., Cardon-Cardo, C., Haimovitz-Friedman, A., Kolesnick, R., Fuks, Z. Nat. Med. (2005) [Pubmed]
  5. Involvement of oxidative stress-induced abnormalities in ceramide and cholesterol metabolism in brain aging and Alzheimer's disease. Cutler, R.G., Kelly, J., Storie, K., Pedersen, W.A., Tammara, A., Hatanpaa, K., Troncoso, J.C., Mattson, M.P. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  6. Perturbation of sphingolipid metabolism and ceramide production in HIV-dementia. Haughey, N.J., Cutler, R.G., Tamara, A., McArthur, J.C., Vargas, D.L., Pardo, C.A., Turchan, J., Nath, A., Mattson, M.P. Ann. Neurol. (2004) [Pubmed]
  7. Ceramide regulates cellular homeostasis via diverse stress signaling pathways. Ruvolo, P.P. Leukemia (2001) [Pubmed]
  8. Novel markers of oxidative stress in actively progressive HIV dementia. Sacktor, N., Haughey, N., Cutler, R., Tamara, A., Turchan, J., Pardo, C., Vargas, D., Nath, A. J. Neuroimmunol. (2004) [Pubmed]
  9. Ganglioside GM1 protection from apoptosis of rat heart fibroblasts. Cavallini, L., Venerando, R., Miotto, G., Alexandre, A. Arch. Biochem. Biophys. (1999) [Pubmed]
  10. Mutations in SPTLC1, encoding serine palmitoyltransferase, long chain base subunit-1, cause hereditary sensory neuropathy type I. Dawkins, J.L., Hulme, D.J., Brahmbhatt, S.B., Auer-Grumbach, M., Nicholson, G.A. Nat. Genet. (2001) [Pubmed]
  11. Structural basis of the interaction of the pyelonephritic E. coli adhesin to its human kidney receptor. Dodson, K.W., Pinkner, J.S., Rose, T., Magnusson, G., Hultgren, S.J., Waksman, G. Cell (2001) [Pubmed]
  12. PML is essential for multiple apoptotic pathways. Wang, Z.G., Ruggero, D., Ronchetti, S., Zhong, S., Gaboli, M., Rivi, R., Pandolfi, P.P. Nat. Genet. (1998) [Pubmed]
  13. Kinase suppressor of Ras is ceramide-activated protein kinase. Zhang, Y., Yao, B., Delikat, S., Bayoumy, S., Lin, X.H., Basu, S., McGinley, M., Chan-Hui, P.Y., Lichenstein, H., Kolesnick, R. Cell (1997) [Pubmed]
  14. 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]
  15. Sphingolipid metabolism and cell growth regulation. Spiegel, S., Merrill, A.H. FASEB J. (1996) [Pubmed]
  16. Fenretinide cytotoxicity for Ewing's sarcoma and primitive neuroectodermal tumor cell lines is decreased by hypoxia and synergistically enhanced by ceramide modulators. Batra, S., Reynolds, C.P., Maurer, B.J. Cancer Res. (2004) [Pubmed]
  17. Ordering of ceramide formation, caspase activation, and Bax/Bcl-2 expression during etoposide-induced apoptosis in C6 glioma cells. Sawada, M., Nakashima, S., Banno, Y., Yamakawa, H., Hayashi, K., Takenaka, K., Nishimura, Y., Sakai, N., Nozawa, Y. Cell Death Differ. (2000) [Pubmed]
  18. Ceramide synthase mediates daunorubicin-induced apoptosis: an alternative mechanism for generating death signals. Bose, R., Verheij, M., Haimovitz-Friedman, A., Scotto, K., Fuks, Z., Kolesnick, R. Cell (1995) [Pubmed]
  19. Acid sphingomyelinase-deficient human lymphoblasts and mice are defective in radiation-induced apoptosis. Santana, P., Peña, L.A., Haimovitz-Friedman, A., Martin, S., Green, D., McLoughlin, M., Cordon-Cardo, C., Schuchman, E.H., Fuks, Z., Kolesnick, R. Cell (1996) [Pubmed]
  20. Absence of hexosaminidase A and B in a normal adult. Dreyfus, J.C., Poenaru, L., Svennerholm, L. N. Engl. J. Med. (1975) [Pubmed]
  21. Phosphorylation of Raf by ceramide-activated protein kinase. Yao, B., Zhang, Y., Delikat, S., Mathias, S., Basu, S., Kolesnick, R. Nature (1995) [Pubmed]
  22. The rate of bulk flow from the Golgi to the plasma membrane. Karrenbauer, A., Jeckel, D., Just, W., Birk, R., Schmidt, R.R., Rothman, J.E., Wieland, F.T. Cell (1990) [Pubmed]
  23. Acidic sphingomyelinase mediates entry of N. gonorrhoeae into nonphagocytic cells. Grassmé, H., Gulbins, E., Brenner, B., Ferlinz, K., Sandhoff, K., Harzer, K., Lang, F., Meyer, T.F. Cell (1997) [Pubmed]
  24. Death of oligodendrocytes mediated by the interaction of nerve growth factor with its receptor p75. Casaccia-Bonnefil, P., Carter, B.D., Dobrowsky, R.T., Chao, M.V. Nature (1996) [Pubmed]
  25. Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Cuvillier, O., Pirianov, G., Kleuser, B., Vanek, P.G., Coso, O.A., Gutkind, S., Spiegel, S. Nature (1996) [Pubmed]
  26. Programmed cell death induced by ceramide. Obeid, L.M., Linardic, C.M., Karolak, L.A., Hannun, Y.A. Science (1993) [Pubmed]
  27. Ceramides modulate programmed cell death in plants. Liang, H., Yao, N., Song, J.T., Luo, S., Lu, H., Greenberg, J.T. Genes Dev. (2003) [Pubmed]
  28. A role for neutral sphingomyelinase-mediated ceramide production in T cell receptor-induced apoptosis and mitogen-activated protein kinase-mediated signal transduction. Tonnetti, L., Verí, M.C., Bonvini, E., D'Adamio, L. J. Exp. Med. (1999) [Pubmed]
  29. Lipopolysaccharide induces disseminated endothelial apoptosis requiring ceramide generation. Haimovitz-Friedman, A., Cordon-Cardo, C., Bayoumy, S., Garzotto, M., McLoughlin, M., Gallily, R., Edwards, C.K., Schuchman, E.H., Fuks, Z., Kolesnick, R. J. Exp. Med. (1997) [Pubmed]
  30. FAN, a novel WD-repeat protein, couples the p55 TNF-receptor to neutral sphingomyelinase. Adam-Klages, S., Adam, D., Wiegmann, K., Struve, S., Kolanus, W., Schneider-Mergener, J., Krönke, M. Cell (1996) [Pubmed]
  31. A ceramide-activated protein phosphatase mediates ceramide-induced G1 arrest of Saccharomyces cerevisiae. Nickels, J.T., Broach, J.R. Genes Dev. (1996) [Pubmed]
  32. The central executioner of apoptosis: multiple connections between protease activation and mitochondria in Fas/APO-1/CD95- and ceramide-induced apoptosis. Susin, S.A., Zamzami, N., Castedo, M., Daugas, E., Wang, H.G., Geley, S., Fassy, F., Reed, J.C., Kroemer, G. J. Exp. Med. (1997) [Pubmed]
  33. CD28 signals through acidic sphingomyelinase. Boucher, L.M., Wiegmann, K., Fütterer, A., Pfeffer, K., Machleidt, T., Schütze, S., Mak, T.W., Krönke, M. J. Exp. Med. (1995) [Pubmed]
  34. Roles for tumor necrosis factor receptor p55 and sphingomyelinase in repairing the cutaneous permeability barrier. Jensen, J.M., Schütze, S., Förl, M., Krönke, M., Proksch, E. J. Clin. Invest. (1999) [Pubmed]
  35. FAS-induced apoptosis is mediated via a ceramide-initiated RAS signaling pathway. Gulbins, E., Bissonnette, R., Mahboubi, A., Martin, S., Nishioka, W., Brunner, T., Baier, G., Baier-Bitterlich, G., Byrd, C., Lang, F. Immunity (1995) [Pubmed]
  36. Increase of ceramide and induction of mixed apoptosis/necrosis by N-(4-hydroxyphenyl)- retinamide in neuroblastoma cell lines. Maurer, B.J., Metelitsa, L.S., Seeger, R.C., Cabot, M.C., Reynolds, C.P. J. Natl. Cancer Inst. (1999) [Pubmed]
  37. Targeting ceramide metabolism--a strategy for overcoming drug resistance. Senchenkov, A., Litvak, D.A., Cabot, M.C. J. Natl. Cancer Inst. (2001) [Pubmed]
  38. Molecular trapping of a fluorescent ceramide analogue at the Golgi apparatus of fixed cells: interaction with endogenous lipids provides a trans-Golgi marker for both light and electron microscopy. Pagano, R.E., Sepanski, M.A., Martin, O.C. J. Cell Biol. (1989) [Pubmed]
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