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Sphingophospholipid


DATA No : PSP5013 INFORMANT : Kentaro Hanada

NAME : Ceramide-1-phosphorylcholine

COMMON NAME: Sphingomyelin
SYMBOL: SM
FORMULA: MOL.WT (average) :


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BIOLOGICAL ACTIVITY
Essential for mammlian cell growth(Ref. 5037/5038) Formation of detergent-resistant lipid-rafts(Ref. 5039/5040) A reservoir of ceramide in ceramide-mediated signalling(Ref. 5017/5035/5036) Anti-colon cancer effect of dietary SM(Ref. 5041) Influences on cholesterol metabolism(Ref. 5042/5043) In hibition of lecthin-cholesterol acyltransferase activity(Ref. 5044) Interaction between cells and substrata(Ref. 5045) Binding to procollagen(Ref. 5046) A receptor to lysenin (an earthworm-derived cytolysin)(Ref. 5047/5038)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:196-198degC(Ref. 5012)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:+6 to 7 (in chloroform/methanol)(Ref. 5012)

DENSITY:

SOLUBILITY:insoluble in water, diethylether, acetone soluble in chloroform, hot ethanol, hot ethylacetate(Ref. 5012)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Ubiquitous in mammalian (probably ubiquitous in vertebtates)
CHEMICAL SYNTHESIS

METABOLISM
SM is formed by phosphorylcholine transfer from phosphatidylcholine to ceramide. SM is degradated to ceramide by acid sphingomyelinase in lysosome, or by neutral sphingomyelinase in the plasma membrane.(Ref. 5002)
GENETIC INFORMATION
Acid sphingomyelinase (mouse and human) (Ref. 5022/5023) An isoform of neutral sphingomyelinase (mouse and human)(Ref. 5048) Genetic defects in acid sphingomyelinase cause Niemann-Pick disease type A and B.(Ref. 5022/5023/5049)
NOTE

REFERENCES
[5002]
AUTHOR:Merrill,A.H.Jr.,and Sweeley,C.C.(1996)Sphingolipids:metabolism and cell signalling(Vance,D.E.,and Vance,J.E.,eds),pp309-339,Elsevier Science B.V.,Amsterdam
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[5012]
AUTHOR:Dawson,Rex M.C.,Elliott,D.C.,Elliott,W.H.,and Jones,K.M. (1986) Data for Biochemical Research (Dawson,Rex M.C.,Elliott,D.C.,Elliott,W.H.,and Jones,K.M., eds), Clarendon Press, Oxford
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[5017]
AUTHOR:Hannun,Y.A.,and Linardic,C.M.
TITLE:Sphingolipid breakdown products: anti-proliferative and tumor-suppressor lipids. PubMed ID:8280742
JOURNAL:Biochim.Biophys.Acta
VOL:1154 PAGE : 223 -236 (1993)
[TOP]

[5022]
AUTHOR:Li,C.M.,Hong,S.B.,Kopal,G.,He,X.,Linke,T.,Hou,W.S.,Koch,J.,Gatt,S.,Sandhoff,K.,Schuchman,E.H.
TITLE:Cloning and characterization of the full-length cDNA and genomic sequences encoding murine acid ceramidase. PubMed ID:9653654
JOURNAL:Genomics
VOL:50 PAGE : 267 -274 (1998)
[TOP]

[5023]
AUTHOR:Koch,J.,Gartner,S.,Li,C.M.,Quintern,L.E.,Bernardo,K.,Levran,O.,Schnabel,D.,Desnick,R.J.,Schuchman,E.H.,Sandhoff,K.
TITLE:Molecular cloning and characterization of a full-length complementary DNA encoding human acid ceramidase. Identification of the first molecular lesion causing Farber disease. PubMed ID:8955159
JOURNAL:J.Biol.Chem.
VOL:271 PAGE : 33110 -33115 (1996)
[TOP]

[5035]
AUTHOR:Hannun,Y.A.
TITLE:Functions of Ceramide in Coordinating Cellular Responses to Stress. PubMed ID:8943189
JOURNAL:Science
VOL:274 PAGE : 1855 -1859 (1996)
[TOP]

[5036]
AUTHOR:Ballou,L.R.,Laulederkind,S.J.F.,Rosloniec,E.F.,and Raghow,R.
TITLE:Ceramide signalling and the immune response. PubMed ID:8664339
JOURNAL:Biochim.Biophys.Acta
VOL:1301 PAGE : 273 -287 (1996)
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[5037]
AUTHOR:Hanada, K., Nishijima, M., Kiso, M., Hasegawa, A., Fujita, S., Ogawa, T., and Akamatsu, Y.
TITLE: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 PubMed ID:1429697
JOURNAL:J Biol Chem.
VOL:267 PAGE : 23527-23533 (1992)
[TOP]

[5038]
AUTHOR:Hanada, K., Hara, T., Fukasawa, M., Yamaji, A., Umeda, M., and Nishijima, M.
TITLE:Mammalian cell mutants resistant to a sphingomyelin-directed cytolysin. Genetic and biochemical evidence for complex formation of the LCB1 protein with the LCB2 protein for serine palmitoyltransferase PubMed ID:9837968
JOURNAL:J Biol Chem.
VOL:273 PAGE : 33787-33794 (1998)
[TOP]

[5039]
AUTHOR:Simons, K., and Ikonen, E.
TITLE:Functional rafts in cell membranes PubMed ID:9177342
JOURNAL:Nature.
VOL:387 PAGE : 569-572 (1997)
[TOP]

[5040]
AUTHOR:Brown, D. A., and London, E.
TITLE:Structure of detergent-resistant membrane domains: does phase separation occur in biological membranes? PubMed ID:9367871
JOURNAL:Biochem Biophys Res Commun.
VOL:240 PAGE : 1-7 (1997)
[TOP]

[5041]
AUTHOR:Dillehay, D. L., Webb, S. K., Schmelz, E. M., and Merrill, A. H., Jr.
TITLE:Dietary sphingomyelin inhibits 1,2-dimethylhydrazine-induced colon cancer in CF1 mice PubMed ID:8169652
JOURNAL:J Nutr.
VOL:124 PAGE : 615-620 (1994)
[TOP]

[5042]
AUTHOR:Porn, M. I., and Slotte, J. P.
TITLE:Reversible effects of sphingomyelin degradation on cholesterol distribution and metabolism in fibroblasts and transformed neuroblastoma cells PubMed ID:2222406
JOURNAL:Biochem J.
VOL:271 PAGE : 121-126 (1990)
[TOP]

[5043]
AUTHOR:Scheek, S., Brown, M. S., and Goldstein, J. L.
TITLE:Sphingomyelin depletion in cultured cells blocks proteolysis of sterol regulatory element binding proteins at site 1 PubMed ID:9326582
JOURNAL:Proc Natl Acad Sci U S A.
VOL:94 PAGE : 11179-11183 (1997)
[TOP]

[5044]
AUTHOR:Bolin, D. J., and Jonas, A.
TITLE:Sphingomyelin inhibits the lecithin-cholesterol acyltransferase reaction with reconstituted high density lipoproteins by decreasing enzyme binding PubMed ID:8702592
JOURNAL:J Biol Chem.
VOL:271 PAGE : 19152-19158 (1996)
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[5045]
AUTHOR:Hidari, Kipj, Ichikawa, S., Fujita, T., Sakiyama, H., and Hirabayashi, Y.
TITLE:Complete removal of sphingolipids from the plasma membrane disrupts cell to substratum adhesion of mouse melanoma cells PubMed ID:8662871
JOURNAL:J Biol Chem.
VOL:271 PAGE : 14636-14641 (1996)
[TOP]

[5046]
AUTHOR:Choglay, A. A., Purdom, I. F., and Hulmes, D. J.
TITLE:Procollagen binding to sphingomyelin PubMed ID:8454585
JOURNAL:J Biol Chem.
VOL:268 PAGE : 6107-6114 (1993)
[TOP]

[5047]
AUTHOR:Yamaji, A., Sekizawa, Y., Emoto, K., Sakuraba, H., Inoue, K., Kobayashi, H., and Umeda, M.
TITLE:Lysenin, a novel sphingomyelin-specific binding protein PubMed ID:9478988
JOURNAL:J Biol Chem.
VOL:273 PAGE : 5300-5306 (1998)
[TOP]

[5048]
AUTHOR:Tomiuk, S., Hofmann, K., Nix, M., Zumbansen, M., and Stoffel, W.
TITLE:Cloned mammalian neutral sphingomyelinase: functions in sphingolipid signaling? PubMed ID:9520418
JOURNAL:Proc Natl Acad Sci U S A.
VOL:95 PAGE : 3638-3643 (1998)
[TOP]

[5049]
AUTHOR:Otterbach, B., and Stoffel, W.
TITLE:Acid sphingomyelinase-deficient mice mimic the neurovisceral form of human lysosomal storage disease (Niemann-Pick disease) PubMed ID:7600574
JOURNAL:Cell.
VOL:81 PAGE : 1053-1061 (1995)
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