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Chemical Compound Review:

Lysosulfatide sodium(2R,3R,4S,5S,6R)-2- [(E,2S,3R)-2...

Synonyms:

Toda, K. et al., Nofer, J.R. et al., Nofer, J.R. et al., Toda, K. et al., Taketomi, T. et al., et al.

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Disease relevance of (2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxy-octadec-4-enoxy]-3,5-dihydroxy-6-methylol-4-sulfoxy-tetrahydropyran

Lysosulfatide (galactosylsphingosine-3-O-sulfate) from metachromatic leukodystrophy and normal human brain [1].
Therefore, the accumulation of lysosulfatide may explain the demyelination in patients with MLD, as is the case with Krabbe disease [2].
Judging from the tissue distribution of the accumulated lysosulfatide and because of the cytotoxicity, the lysosulfatide presumably explains the demyelination seen in the nervous tissues of patients with metachromatic leukodystrophy [3].
The inhibitory effects of HDL, SPC, and LSF on TNF-alpha-induced E-selectin expression were partially reverted in the presence of suramin, an antagonist of lysosphingolipid receptor EDG-3, or pertussis toxin, an inhibitor of trimeric G proteins [4].

High impact information on (2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxy-octadec-4-enoxy]-3,5-dihydroxy-6-methylol-4-sulfoxy-tetrahydropyran

The vasoactive effects of HDL could be mimicked by three lysophospholipids present in HDL: sphingosylphosphorylcholine (SPC), sphingosine-1-phosphate (S1P), and lysosulfatide (LSF) [5].
Two bioactive lysosphingolipids present in HDL particles, sphingosylphosphorylcholine and lysosulfatide, fully mimicked the survival effect of HDL by blocking the mitochondrial pathway of apoptosis and potently activating Akt [6].
Like native HDL, LSF and SPC induced PtdInsP(2) turnover, Ca(2+) mobilization, and fibroblast proliferation [7].
Lysosulfatide (sulfogalactosylsphingosine) accumulation in tissues from patients with metachromatic leukodystrophy [2].
The concentration of lysosulfatide was high in the cerebral white matter, spinal cord, and sciatic nerve (223-1,172 pmol/mg of protein) [2].

Associations of (2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxy-octadec-4-enoxy]-3,5-dihydroxy-6-methylol-4-sulfoxy-tetrahydropyran with other chemical compounds

As is the case with galactosylsphingosine, lysosulfatide inhibited cytochrome c oxidase activity, in a dose-dependent manner [3].
In addition, inhibition of activation of protein kinase Akt with LY294002 but not inhibition of phosphatidylinositol-specific phospholipase C (PI-PLC) with U73122 abolished the restrictive effects of HDL-, SPC-, or LSF on E-selectin expression [4].
Thin layer chromatography of lysosulfatide showed anomalous Rf-values in contrast with such lysosphingolipids as glucopsychosine and galactopsychosine with neutral, acidic, and alkaline developing solvents [8].

Analytical, diagnostic and therapeutic context of (2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxy-octadec-4-enoxy]-3,5-dihydroxy-6-methylol-4-sulfoxy-tetrahydropyran

We describe here a sensitive assay method for lysosulfatide (sulfogalactosylsphingosine) in human tissues using HPLC [2].
Thus, the chemical structure of lysosulfatide was confirmed by fast atom bombardment mass spectrometry and 13C- and 1H-NMR spectroscopy [8].

References

Lysosulfatide (galactosylsphingosine-3-O-sulfate) from metachromatic leukodystrophy and normal human brain. Rosengren, B., Fredman, P., Månsson, J.E., Svennerholm, L. J. Neurochem. (1989) [Pubmed]
Lysosulfatide (sulfogalactosylsphingosine) accumulation in tissues from patients with metachromatic leukodystrophy. Toda, K., Kobayashi, T., Goto, I., Ohno, K., Eto, Y., Inui, K., Okada, S. J. Neurochem. (1990) [Pubmed]
Accumulation of lysosulfatide (sulfogalactosylsphingosine) in tissues of a boy with metachromatic leukodystrophy. Toda, K., Kobayashi, T., Goto, I., Kurokawa, T., Ogomori, K. Biochem. Biophys. Res. Commun. (1989) [Pubmed]
High density lipoprotein-associated lysosphingolipids reduce E-selectin expression in human endothelial cells. Nofer, J.R., Geigenmüller, S., Göpfert, C., Assmann, G., Buddecke, E., Schmidt, A. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
HDL induces NO-dependent vasorelaxation via the lysophospholipid receptor S1P3. Nofer, J.R., van der Giet, M., Tölle, M., Wolinska, I., von Wnuck Lipinski, K., Baba, H.A., Tietge, U.J., Gödecke, A., Ishii, I., Kleuser, B., Schäfers, M., Fobker, M., Zidek, W., Assmann, G., Chun, J., Levkau, B. J. Clin. Invest. (2004) [Pubmed]
Suppression of endothelial cell apoptosis by high density lipoproteins (HDL) and HDL-associated lysosphingolipids. Nofer, J.R., Levkau, B., Wolinska, I., Junker, R., Fobker, M., von Eckardstein, A., Seedorf, U., Assmann, G. J. Biol. Chem. (2001) [Pubmed]
Activation of phosphatidylinositol-specific phospholipase C by HDL-associated lysosphingolipid. Involvement in mitogenesis but not in cholesterol efflux. Nofer, J.R., Fobker, M., Höbbel, G., Voss, R., Wolinska, I., Tepel, M., Zidek, W., Junker, R., Seedorf, U., von Eckardstein, A., Assmann, G., Walter, M. Biochemistry (2000) [Pubmed]
New approach for characterization of lysosulfatide by TLC, fast atom bombardment mass spectrometry and NMR spectroscopy. Taketomi, T., Hara, A., Kutsukake, Y., Sugiyama, E. J. Biochem. (1990) [Pubmed]

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