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 |
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 | : | 80-84 /79-81; 82.5-83C (Ref. 5012) |
|
| BOILING POINT | : | |
|
| REFRACTIVE INDEX | : | |
|
| OPTICAL ROTATION | : | [a]D =+3.25 (Ref. 5012) |
|
| DENSITY | : | |
|
| SOLUBILITY | : | Insol. in water. Soluble in CHCl3, EtOH and MeOH (Ref. 5012) |
| 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 | : |
|
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)
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)
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[0032]
| AUTHOR | : | Karlsson, K.-A. |
| TITLE | : | Sphingolipid long chain bases. PubMed ID:4921900 |
| JOURNAL | : | Lipids |
| VOL | : | 5 PAGE : 878 -891 (1970) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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 : - () |
[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 : - () |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.
