Back to HOME

Long chain base and Ceramide


DATA No : DLB0019 INFORMANT : Akira Hayashi

NAME : 4-Sphingenine / D-Erytjro-1,3-dihydroxy-2-amino-trans-4-octadecene , 2S, 3R, 4E-form (Ref. 0032/0034)

COMMON NAME: Sphingosine
SYMBOL: d18:1 (4)
FORMULA: C18H37O2N1 MOL.WT (average) : 299.492


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Inhibitor for protein kinase C (Ref. 0036/0037/0038); Inhibition of protein kinase C, sec-kinase, calmodulin-dependent enzymes, insulin receptor tyrosine kinase, CTP:phosphocholine cytidyltransferase, phosphatidic acid phosphohydrase, 150 kDa diacylglycerol kinase, and thyrotropin-releasing hormone binding (Ref. 5017); Inhibition of RNA primase (Ref. 5018) ; Inhibition of monoacylglycerol acyltransferase (Ref. 0519); Activation of casein kinase, EGF-receptor tyrosine kinase, phospholipase D, and 80 kDa
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:80-84deg/79-81deg; 82.5-83degC (Ref. 5012)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D =+3.25deg (Ref. 5012)

DENSITY:

SOLUBILITY:Insol. in water. Soluble in CHCl3, EtOH and MeOH (Ref. 5012)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:trans double bond (980cm-1, 10.3nm)

NMR SPECTRA:1H-NMR (Ref. 0260)/ 220MHz-1H-NMR (Ref. 0262)

MASS SPECTRA:EI/MS of N-acetyl-O-TMS derivative (Ref. 0002/0014)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Sphingomyelin of human plasma (Ref. 0014); Sphingoglycolipids from Ostrea gigas (Ref. 0002); Ceramide aminoethylphosphonate from Ostrea gigas (adductor muscle 4.7%, gills 25.3%, mantle 23.0%, viscera 17.9%) (Ref. 0008); Sphingophosphonolipids obtained from eight kinds of shellfish (10.2-41.5%) (Ref. 0006); Aminoalkylphosphonyl cerebroside from Turbo cornutus (muscle part 14.6% (Ref. 0007), visceral part 18.0% (Ref. 0008) ); N-Methylaminoethylphosphonyl trigalactosyl ceramide from Turbo cornutus (Ref. 0009); Five kinds of sphingoglycolipids obtained from Turbo cornutus (26.6-43.5%) (Ref. 0010); Five kinds of Gala-6 series glycolipids from Chlorostoma argyrostoma turbinatum (16.6-30.6%) (Ref. 0011); Barnea dilatata japonica (cerebroside 11.5%, ceramide aminoethylphosphonate 13.5%) (Ref. 0031); Ubiquitous in eukaryotes, limited types of prokaryotes (Ref. 5001)
CHEMICAL SYNTHESIS
(Ref. 5024/5025/5026)
METABOLISM
Sphingosine is not a direct precursor for ceramide synthesis in the de novo synthetic pathway, although exogenous sphingosine is converted to ceramide probably by the same enzyme as dihydrosphingosine-N-acyltransferase in cells. Thus, cellular sphingosine is mainly produced by hydrolysis of ceramide. Sphingosine is converted to Sphingossine-7-phosphate in the degradation pathway. (Ref. 5002)
GENETIC INFORMATION
Sphingosine kinase (yeast and mouse) (Ref. 5014/5015); Acid ceramidase (mouse and human) (Ref. 5022/5023)
NOTE

REFERENCES
[0002]
AUTHOR:Hayashi, A. and Matsubara. T.
TITLE:Determination of the structure of sphinga-4,8-dienine from oyster glycolipids by gas chromatography and mass spectrometry. PubMed ID:4331787
JOURNAL:Biochim. Biophys. Acta
VOL:248 PAGE : 306 -314 (1971)
[TOP]

[0006]
AUTHOR:Matsubara, T.
TITLE:Distribution of the dienic long chain bases in shellfish sphingophosphonolipids.
JOURNAL:Chem. Phys. Lipids
VOL:14 PAGE : 247 -259 (1975)
[TOP]

[0007]
AUTHOR:Hayashi, A. and Matsuura, F.
TITLE:Characterization of aminoalkylphophonyl cerebrosides in muscle tissue of Turbo cornutus. PubMed ID:699219
JOURNAL:Chem. Phys. Lipids
VOL:22 PAGE : 9 -23 (1978)
[TOP]

[0008]
AUTHOR:Matsuura, F.
TITLE:Phosphonosphingoglycolipid, a novel sphingolipid from the viscera of Turbo cornutus. PubMed ID:890866
JOURNAL:Chem. Phys. Lipids
VOL:19 PAGE : 223 -242 (1977)
[TOP]

[0009]
AUTHOR:Hayashi, A. and Matsubara, T.
TITLE:A new homologue of phosphonosphingolipid, N-methylaminoethyl-phosphonyltrigalactosylceramide.
JOURNAL:Biochim. Biophys. Acta
VOL:1006 PAGE : 89 -96 (1989)
[TOP]

[0010]
AUTHOR:Matsubara, T., and Hayashi, A.
TITLE:Structural studies on glycolipid of shellfish. III. Novel glycolipids from Turbo cornutus PubMed ID:6263873
JOURNAL:J Biochem (Tokyo).
VOL:89 PAGE : 645-650 (1981)
[TOP]

[0011]
AUTHOR:Matsubara, T., and Hayashi, A.
TITLE:Structural studies on glycolipids of shellfish. V. Gala-6 series glycosphingolipids of the marine snail, Chlorostoma argyrostoma turbinatum PubMed ID:3011773
JOURNAL:J Biochem (Tokyo).
VOL:99 PAGE : 1401-1408 (1986)
[TOP]

[0014]
AUTHOR:Polito, A. J., Akita, T., and Sweeley, C. C.
TITLE:Gas chromatography and mass spectrometry of sphingolipid bases. Characterization of sphinga-4,14-dienine from plasma sphingomyelin PubMed ID:5660077
JOURNAL:Biochemistry.
VOL:7 PAGE : 2609-2614 (1968)
[TOP]

[0031]
AUTHOR:Mishima, Y. and Hayashi, A.
TITLE:Studies on sphingolipids of Barnea (Umitakea) dilatata japonica I. Cerebroside and Ceramide aminoethylphosphonate (in Japanene )
JOURNAL: Japan. Oil Chem. Soc. (Yukagaku )
VOL:27 PAGE : 92 -97 (1978)
[TOP]

[0032]
AUTHOR:Karlsson, K.-A.
TITLE:Sphingolipid long chain bases. PubMed ID:4921900
JOURNAL:Lipids
VOL:5 PAGE : 878 -891 (1970)
[TOP]

[0034]
AUTHOR:Carter, H.E., Glick, F.J., Norris, W.P., and Phillips, G.E.
TITLE:Biochemistry of the sphingosine III. Structure of sphingosine
JOURNAL:J. Biol. Chem.
VOL:170 PAGE : 285 -294 (1947)
[TOP]

[0036]
AUTHOR:Hannun, Y. A., Loomis, C. R., Merrill, A. H., Jr., and Bell, R. M.
TITLE:Sphingosine inhibition of protein kinase C activity and of phorbol dibutyrate binding in vitro and in human platelets PubMed ID:3462188
JOURNAL:J Biol Chem.
VOL:261 PAGE : 12604-12609 (1986)
[TOP]

[0037]
AUTHOR:Merrill, A. H., Jr., Sereni, A. M., Stevens, V. L., Hannun, Y. A., Bell, R. M., and Kinkade, J. M., Jr.
TITLE:Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases PubMed ID:3462189
JOURNAL:J Biol Chem.
VOL:261 PAGE : 12610-12615 (1986)
[TOP]

[0038]
AUTHOR:Hall, F. L., Fernyhough, P., Ishii, D. N., and Vulliet, P. R.
TITLE:Suppression of nerve growth factor-directed neurite outgrowth in PC12 cells by sphingosine, an inhibitor of protein kinase C PubMed ID:3162237
JOURNAL:J Biol Chem.
VOL:263 PAGE : 4460-4466 (1988)
[TOP]

[0260]
AUTHOR:Ando, S.
TITLE:Recent progress in the structural stdies of glycolipids (in Japanese)
JOURNAL:J. Jpn. Oil Chem. Soc.
VOL:21 PAGE : 243 -256 (1972)
[TOP]

[0262]
AUTHOR:Martin-Lomas, M., and Chapman, D.
TITLE:Structural studies on glycolipids, Part I : 220MHz PMR spectra of acetylated galactocerebroside.
JOURNAL:Chem. Phys. Lipids
VOL:10 PAGE : 152 -164 (1973)
[TOP]

[5001]
AUTHOR:Karlsson, K-A.
TITLE:On the Chemistry and Occurrence of Sphingolipid Long-Chain Bases. PubMed ID:4394487
JOURNAL:Chem. Phys. Lipids
VOL:5 PAGE : 6 -43 (1970)
[TOP]

[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 : - ()
[TOP]

[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]

[5014]
AUTHOR:Nagiec, M.M., Skrzypek, M., Nagiec, E.E., Lester, R.L., and Dickson, R.C.
TITLE:The LCB4 (YOR171c) and LCB5 (YLR260w) Genes of Saccharomyces Encode Sphingoid Long Chain Base Kinases. PubMed ID:9677363
JOURNAL:J. Biol. Chem.
VOL:273 PAGE : 19437 -19442 (1998)
[TOP]

[5015]
AUTHOR:Kohama, T., Olivera, A., Edsall, L., Nagiec, M.M., Dickson, R., and Spiegel, S.
TITLE:Molecular Cloning and Functional Characterization of Murine Sphingosine Kinase. PubMed ID:9726979
JOURNAL:J. Biol. Chem.
VOL:273 PAGE : 23722 -23728 (1998)
[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]

[5018]
AUTHOR:Simbulan, C.M.G., Tamiya-Koizumi, K.,S uzuki, M., Shoji, M., Taki, T., and Yoshida, S.
TITLE:Sphingosine Inhibits the Synthesis of RNA Primers by Primase in Vitro. PubMed ID:7519054
JOURNAL:Biochemistry
VOL:33 PAGE : 9007 -9012 (1994)
[TOP]

[5021]
AUTHOR:Hashizume, T., Nakao, M., Sato, T.
TITLE:Sphingosine enhances phosphatidylinositol 4-kinase activity in rabbit platelets. PubMed ID:8864845
JOURNAL:J. Biochem.
VOL:120 PAGE : 61 -65 (1996)
[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]

[5024]
AUTHOR:Fujita, S., Sugimoto, M., Tomita, K., Nakahara, Y., and Ogawa, T.
TITLE:Enantiospecific Syntheses of Sphingosine and Ceramide Stereoisomers with 3S Configuration from D-Glucose
JOURNAL:Agric. Biol. Chem.
VOL:55 PAGE : 2561 -2569 (1991)
[TOP]

[5025]
AUTHOR:Kiso, M., Nakamura, A. Tomita, Y., and Hasegawa, A .
TITLE:A novel route to D-erythro-sphingosine and related compounds from mono-O-isopropylidene-D-xylose or -D-galactose
JOURNAL:Carbohydrate Res.
VOL:158 PAGE : 101 -111 (1986)
[TOP]

[5026]
AUTHOR:Kobayashi, S., Hayashi, T., and Kawasuji, T.
TITLE:Enantioselective Syntheses of D-erythro-Sphingosine and Phytosphingosine from Simple Achiral Aldehydes Using Catalytic Asymmetric Aldol Reactions as Key Steps
JOURNAL:Tetrahedron Lett.
VOL:35 PAGE : 9573 -9576 (1994)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.