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Glycosphingolipid


DATA No : GSG0069 INFORMANT : Ineo Ishizuka

NAME : Galactosylceramide 3-sulfate

COMMON NAME: Galactosyl sulfatide
SYMBOL: SM4s, SGC
FORMULA: MOL.WT (average) :


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Review (Ref. 0208). Inhibition of the arylsulfatase A activity (Ref. 0003/0006/0010/0011/0012/0013/0016/0047/0048/0054). Myelin components (Ref. 0016/0023). Interaction with GM2 activator protein (Ref. 0238). Stimulation of the evolution of oxygen radicals in polymorphonuclear leukocytes (Ref. 0024). Cannot be hydrolyzed by glucosulfatase (Ref. 0015). Mouse monoclonal antibodies (Ref. 0043/0050). Regulation of sulfotransferase activity (Ref. 0240).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:Behavior in the Folch partition (Ref. 0027). Precipitates from hot methanol (Ref. 0004).
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:820cm-1 (Ref. 0001/0029/0031).

NMR SPECTRA:H-C COSY spectrum of sulfatide (Ref. 1498)
[Spectrum 0001](I.Ishizuka)
DQF COSY spectrum of sulfatide
[Spectrum 0002](I.Ishizuka)

MASS SPECTRA:EI-MS (Ref. 0033), SI-MS (Ref. 0036).TLC-blotting/negative-ion LSIMS of galactosyl sulfatide
[Spectrum 0003](I.Ishizuka)

OTHER SPECTRA:Absorption of the complex with Azure A the abssorption of the acetates of sulfoglycolipids with Azure A (Ref. 0027).
CHROMATOGRAM DATA

2D TLC of male
[Chromatogram 0001]and female
[Chromatogram 0002] wild type and CGK-KO mice(I.Ishizuka).
DEAE Sephadex column chromatography of female wild type and CGK-KO mice
[Chromatogram 0003](I.Ishizuka).
SOURCE
Review (Ref. 0208). Bull frog and axolotl (Ref. 0237); Human brain (Ref. 0002/0001); the white and gray matter of the human brain (Ref. 0009); rabbit brain, white matter (Ref. 0057). Rat brain (Ref. 0017/0020), effect of chronic treatment with diazepam (Ref. 0055), regional distribution (Ref. 0020). Human kidney (aged, 0.39; middle age, 0.40; juvenile, 0.48mg/g dry tissue (Ref. 0004). Porcine pancreas (Ref. 0031), rabbit stomach (antrum, pylorus), duodenum jejunum (Ref. 0053). Brain (review) (Ref. 0016). C6 glioma derived from rat brain (Ref. 0032), cod brain (Ref. 0021). Mouse (C57BL) kidney (Ref. 0230), brain, liver, kidney (Ref. 0231).
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
The fatty acid composition, human kidney:22:0, 23:0, 24:0, 24:1, h24:0, h23:0, h24:1 (Ref. 0004)
REFERENCES
[0001]
AUTHOR:Yamakawa, T., Kiso, N., Handa, S., Makita, A., and Yokoyama, S.
TITLE:On the structure of brain cerebroside sulfuric ester and ceramide dihexoside of erythrocytes PubMed ID:14002299
JOURNAL:J Biochem (Tokyo).
VOL:52 PAGE : 226-227 (1962)
[TOP]

[0002]
AUTHOR:Thudichum,J.L.W.(1874) Researches on the chemical constitution of the brain in report of the Medical Officer of the Privy Council, London, n.S., No. 3, append. 5, pp113-247
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JOURNAL:
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[0003]
AUTHOR:Mehl, E., and Jatzkewitz, H.
TITLE:[A cerebrosidesulfatase from swine kidney] PubMed ID:5829234
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:339 PAGE : 260-276 (1964)
[TOP]

[0004]
AUTHOR:Martensson, E.
TITLE:Sulfatides of human kidney. Isolation, identification, and fatty acid composition PubMed ID:5963014
JOURNAL:Biochim Biophys Acta.
VOL:116 PAGE : 521-531 (1966)
[TOP]

[0006]
AUTHOR:Mehl,E., and Jatzkewitz,H.
TITLE:Cerebroside 3-sulfate as a physiological substrate of arylsulfatase A PubMed ID:5646041
JOURNAL:Biochim. Biophys. Acta
VOL:151 PAGE : 619 -627 (1968)
[TOP]

[0009]
AUTHOR:Neskovic,N.,Sarlieve,L.,Nussbaum,J.-L.,Kostic,D., and Mandel,P.
TITLE:Quantitative thin-layer chromatography of glycolipids in animal tissues. PubMed ID:5031779
JOURNAL:Clin. Chim. Acta
VOL:38 PAGE : 147 -153 (1972)
[TOP]

[0010]
AUTHOR:Harzer, K., and Benz, H. U.
TITLE:Deficiency of lactosyl sulfatide sulfatase in metachromatic leucodystrophy (sulfatidosis) PubMed ID:4140140
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:355 PAGE : 744-748 (1974)
[TOP]

[0011]
AUTHOR:Mraz, W., and Jatzkewitz, H.
TITLE:Cerebroside sulphatase activity of arylsulphatases from various invertebrates PubMed ID:4435712
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:355 PAGE : 33-44 (1974)
[TOP]

[0012]
AUTHOR:Stinshoff,K., and Jatzkewitz,H.
TITLE:Comparison of the cerebroside sulphatase and the arylsulphatase activity of human sulphatase a in the absence of activators. PubMed ID:235289
JOURNAL:Biochim. Biophys. Acta
VOL:377 PAGE : 126 -138 (1975)
[TOP]

[0013]
AUTHOR:Fischer, G., and Jatzkewitz, H.
TITLE:The activator of cerebroside sulphatase. Purification from human liver and identification as a protein PubMed ID:239890
JOURNAL:Hoppe Seylers Z Physiol Chem.
VOL:356 PAGE : 605-613 (1975)
[TOP]

[0015]
AUTHOR:Hatanaka,H.,Egami,F.,Ishizuka,I., and Nagai,Y.
TITLE:Sulphogalatolipid sulphohydrolase activity of arylsulfatase purified from a marine gastropod Charonia lampas. PubMed ID:938679
JOURNAL:Biochim. Biophys. Acta
VOL:438 PAGE : 176 -185 (1976)
[TOP]

[0016]
AUTHOR:Farooqui,A.A.,Rebel,G., and Mandel, P.
TITLE:Sulphatide metabolism in brain. PubMed ID:320417
JOURNAL:Life Sci.
VOL:20 PAGE : 569 -583 (1977)
[TOP]

[0017]
AUTHOR:Pollet, S., Ermidou, S., Le Saux, F., Monge, M., and Baumann, N.
TITLE:Microanalysis of brain lipids: multiple two-dimensional thin-layer chromatography PubMed ID:712251
JOURNAL:J Lipid Res.
VOL:19 PAGE : 916-921 (1978)
[TOP]

[0020]
AUTHOR:Nonaka,G., and Kishimoto,Y.
TITLE:Levels of cerebrosides, sulfatides, and galactosyl diglycerides in different regions of rat brain.Change during maturation and distributionin subcellular fractions of gray and white matter of sheep brain. PubMed ID:435504
JOURNAL:Biochim. Biophys. Acta
VOL:572 PAGE : 432 -441 (1979)
[TOP]

[0021]
AUTHOR:Tamai,Y.,Kojima,H.,Abe,K.,and Saito,S.(1982) Glycolipid composition of fish brains and its bearing on the phylogeny in New Vistas in Glycolipid Research , (Makita,A., Handa,S., Taketomi, T., and nagai,Y., eds), pp315-323, Plenum press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0023]
AUTHOR:Burkart, T., Caimi, L., Siegrist, H. P., Herschkowitz, N. N., and Wiesmann, U. N.
TITLE:Vesicular transport of sulfatide in the myelinating mouse brain. Functional association with lysosomes? PubMed ID:6949901
JOURNAL:J Biol Chem.
VOL:257 PAGE : 3151-3156 (1982)
[TOP]

[0024]
AUTHOR:Kakinuma, K., Yamaguchi, T., Suzuki, H., and Nagai, Y.
TITLE:Sulfatide activation of the oxygen radical generating system of leucocytes PubMed ID:7128820
JOURNAL:FEBS Lett.
VOL:145 PAGE : 16-20 (1982)
[TOP]

[0027]
AUTHOR:Tadano-Aritomi,K., and Ishizuka,I.
TITLE:Determination of peracetylated sulfoglycolipids using the azure A method. PubMed ID:6196425
JOURNAL:J. Lipid Res.
VOL:24 PAGE : 1368 -1375 (1983)
[TOP]

[0029]
AUTHOR:Saito,S., and Tamai,Y.
TITLE:Characteristic constituents of glycolipids from frog and sciatic nerve. PubMed ID:6603493
JOURNAL:J. Neurochem.
VOL:41 PAGE : 737 -744 (1983)
[TOP]

[0031]
AUTHOR:Nakamura,K.,Fujita,R.,Uemo,K., and Handa,S.
TITLE:Glycosphingolipids of porcine pancreas. PubMed ID:6746593
JOURNAL:J. Biochem.
VOL:95 PAGE : 1137 -1144 (1984)
[TOP]

[0032]
AUTHOR:Tocque, B., Albouz, S., Boutry, J. M., Le Saux, F., Hauw, J. J., Bourdon, R., Baumann, N., and Zalc, B.
TITLE:Desipramine elicits the expression of opiate receptors and sulfogalactosylceramide synthesis in rat C6 glioma cells PubMed ID:6321658
JOURNAL:J Neurochem.
VOL:42 PAGE : 1101-1106 (1984)
[TOP]

[0033]
AUTHOR:Ishizuka, I., and Tadano-Aritomi, K.
TITLE:Characterization of sulfoglycosphingolipids by direct probe electron impact mass spectrometry PubMed ID:6501265
JOURNAL:J Biochem (Tokyo).
VOL:96 PAGE : 829-839 (1984)
[TOP]

[0036]
AUTHOR:Kushi, Y., Handa, S., and Ishizuka, I.
TITLE:Secondary ion mass spectrometry for sulfoglycolipids: application of negative ion detection PubMed ID:4008462
JOURNAL:J Biochem (Tokyo).
VOL:97 PAGE : 419-428 (1985)
[TOP]

[0043]
AUTHOR:Goujet-Zalc,C.,Guerci,A.,Dubois,G., and Zalc,B.
TITLE:Schwann cell marker defined by a monoclonal antibody (224-58) with species cross-reactivity. II. Molecular characterization of the epitope. PubMed ID:2416875
JOURNAL:J. Neurochem.
VOL:46 PAGE : 435 -439 (1986)
[TOP]

[0047]
AUTHOR:Conzelmann, E., and Sandhoff, K.
TITLE:Activator proteins for lysosomal glycolipid hydrolysis PubMed ID:2885714
JOURNAL:Methods Enzymol.
VOL:138 PAGE : 792-815 (1987)
[TOP]

[0048]
AUTHOR:Farooqui,A.A.
TITLE:Clinical and metabolic aspects of sulfohydrolases in man. PubMed ID:3307326
JOURNAL:Adv. Clin. Chem.
VOL:26 PAGE : 157 -201 (1987)
[TOP]

[0050]
AUTHOR:Fredman,P.,Mattson,L.,Andersson,K.,Davidsson,P.,Ishizuka,I.,Jeansson,S., Mansson,J.E., and Svennerholm,L.
TITLE:Characterization of the binding epitope of a monoclonal antibody to sulphatide. PubMed ID:2455508
JOURNAL:Biochem. J.
VOL:251 PAGE : 17 -22 (1988)
[TOP]

[0053]
AUTHOR:Natomi, H., Sugano, K., Iwamori, M., Takaku, F., and Nagai, Y.
TITLE:Region-specific distribution of glycosphingolipids in the rabbit gastrointestinal tract: preferential enrichment of sulfoglycolipids in the mucosal regions exposed to acid PubMed ID:3390457
JOURNAL:Biochim Biophys Acta.
VOL:961 PAGE : 213-222 (1988)
[TOP]

[0054]
AUTHOR:Roy, A. B., and Mantle, T. J.
TITLE:The anomalous kinetics of sulphatase A PubMed ID:2572216
JOURNAL:Biochem J.
VOL:261 PAGE : 689-697 (1989)
[TOP]

[0055]
AUTHOR:Vrbaski,S.R.,Ristic,V.I.,Petrovic,G.T., and Ristic,M.S.
TITLE:Brain lipids in rat after chronic diazepam treatment. PubMed ID:2753868
JOURNAL:J. Biochem.
VOL:105 PAGE : 705 -707 (1989)
[TOP]

[0057]
AUTHOR:Kean, E. L.
TITLE:Rapid, sensitive spectrophotometric method for quantitative determination of sulfatides PubMed ID:5646183
JOURNAL:J Lipid Res.
VOL:9 PAGE : 319-327 (1968)
[TOP]

[0208]
AUTHOR:Ishizuka, I.
TITLE:Chemistry and functional distribution of sulfoglycolipids PubMed ID:9640458
JOURNAL:Prog Lipid Res.
VOL:36 PAGE : 245-319 (1997)
[TOP]

[0230]
AUTHOR:Deshmukh, G. D., Radin, N. S., Gattone, V. H., 2nd, and Shayman, J. A.
TITLE:Abnormalities of glycosphingolipid, sulfatide, and ceramide in the polycystic (cpk/cpk) mouse PubMed ID:7806975
JOURNAL:J Lipid Res.
VOL:35 PAGE : 1611-1618 (1994)
[TOP]

[0231]
AUTHOR:Igisu, H., and Suzuki, K.
TITLE:Glycolipids of the spinal cord, sciatic nerve, and systemic organs of the twitcher mouse PubMed ID:6693925
JOURNAL:J Neuropathol Exp Neurol.
VOL:43 PAGE : 22-36 (1984)
[TOP]

[0237]
AUTHOR:Tamai, Y., Kojima, H., Saito, S., Uchida, K., Kitajima, R; Komatsu, H., and Moriya, T.
TITLE:Metamorphic changes in glycolipids and myelin proteins and 2',3'-cyclic nucleotide 3'-phosphohydrolase in bullfrog and axolotl brain. PubMed ID:8386225
JOURNAL:J. Neurochem.
VOL:60 PAGE : 1854 -1863 (1993)
[TOP]

[0238]
AUTHOR:Hama, Y., Li, Y. T., and Li, S. C.
TITLE:Interaction of GM2 activator protein with glycosphingolipids PubMed ID:9006924
JOURNAL:J Biol Chem.
VOL:272 PAGE : 2828-2833 (1997)
[TOP]

[0240]
AUTHOR:Yabunaka, N., Honke, K., Ishii, A., Ogiso, Y., Kuzumaki, N., Agishi, Y., and Makita, A.
TITLE:Involvement of Ras in the expression of glycolipid sulfotransferase in human renal cancer cells PubMed ID:9178817
JOURNAL:Int J Cancer.
VOL:71 PAGE : 620-623 (1997)
[TOP]

[1498]
AUTHOR:Taki, T., Kuroyanagi, M., Yoshioka, H., and Handa, S.
TITLE:13C-nuclear magnetic resonance of glycosphingolipids PubMed ID:1639757
JOURNAL:J Biochem (Tokyo).
VOL:111 PAGE : 614-619 (1992)
[TOP]

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