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Sphingophospholipid


DATA No : PSP6002 INFORMANT : Takehiko Yokomizo

NAME : sphingosylphosphorylcholine

COMMON NAME: lysosphingomyelin
SYMBOL: SPC
FORMULA: C23H49N2O5P MOL.WT (average) : 464.619


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BIOLOGICAL ACTIVITY
Mobilizes intracellular calcium stores (Ref. 6008) probably via several G protein-coupled receptors, such as OGR1 and GPR4 (Ref. 6014/6015). It regulates numerous cellular functions including cell proliferation (Ref. 6009), cell growth inhibition, smooth muscle contraction, neurite outgrowth (Ref. 6010), and actin rearrangement (Ref. 6013). Activates MAP kinase (Ref. 6012) and transcription factor AP-1 (Ref. 6011).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:It is difficult to suspend SPC using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution. The solubility of stock solutions may be increased by the addition of dimethylamine.
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:ESI/MS (Ref. 4509).

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM
Synthesized by sphingomyelin deacetylase (undiscovered enzyme) (Ref. 6008/6010).
GENETIC INFORMATION

NOTE

REFERENCES
[6008]
AUTHOR:Yule, D. I., Wu, D., Essington, T. E., Shayman, J. A., and Williams, J. A.
TITLE:Sphingosine metabolism induces Ca2+ oscillations in rat pancreatic acinar cells PubMed ID:8509375
JOURNAL:J Biol Chem.
VOL:268 PAGE : 12353-12358 (1993)
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[6009]
AUTHOR:Desai, N. N., Carlson, R. O., Mattie, M. E., Olivera, A., Buckley, N. E., Seki, T., Brooker, G., and Spiegel, S.
TITLE:Signaling pathways for sphingosylphosphorylcholine-mediated mitogenesis in Swiss 3T3 fibroblasts PubMed ID:8389770
JOURNAL:J Cell Biol.
VOL:121 PAGE : 1385-1395 (1993)
[TOP]

[6010]
AUTHOR:Sugiyama, E., Uemura, K., Hara, A., and Taketomi, T.
TITLE:Metabolism and neurite promoting effect of exogenous sphingosylphosphocholine in cultured murine neuroblastoma cells PubMed ID:8514735
JOURNAL:J Biochem (Tokyo).
VOL:113 PAGE : 467-472 (1993)
[TOP]

[6011]
AUTHOR:Berger, A., Rosenthal, D., and Spiegel, S.
TITLE:Sphingosylphosphocholine, a signaling molecule which accumulates in Niemann-Pick disease type A, stimulates DNA-binding activity of the transcription activator protein AP-1 PubMed ID:7597047
JOURNAL:Proc Natl Acad Sci U S A.
VOL:92 PAGE : 5885-5889 (1995)
[TOP]

[6012]
AUTHOR:Seufferlein, T., and Rozengurt, E.
TITLE:Sphingosylphosphorylcholine activation of mitogen-activated protein kinase in Swiss 3T3 cells requires protein kinase C and a pertussis toxin-sensitive G protein PubMed ID:7592645
JOURNAL:J Biol Chem.
VOL:270 PAGE : 24334-24342 (1995)
[TOP]

[6013]
AUTHOR:Seufferlein, T., and Rozengurt, E.
TITLE:Sphingosylphosphorylcholine rapidly induces tyrosine phosphorylation of p125FAK and paxillin, rearrangement of the actin cytoskeleton and focal contact assembly. Requirement of p21rho in the signaling pathway PubMed ID:7592646
JOURNAL:J Biol Chem.
VOL:270 PAGE : 24343-24351 (1995)
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[6014]
AUTHOR:Xu, Y., Zhu, K., Hong, G., Wu, W., Baudhuin, L. M., Xiao, Y., and Damron, D. S.
TITLE:Sphingosylphosphorylcholine is a ligand for ovarian cancer G-protein-coupled receptor 1 PubMed ID:10806476
JOURNAL:Nat Cell Biol.
VOL:2 PAGE : 261-267 (2000)
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[6015]
AUTHOR:Zhu, K., Baudhuin, L. M., Hong, G., Williams, F. S., Cristina, K. L., Kabarowski, J. H., Witte, O. N., and Xu, Y.
TITLE:Sphingosylphosphorylcholine and lysophosphatidylcholine are ligands for the G protein-coupled receptor GPR4 PubMed ID:11535583
JOURNAL:J Biol Chem.
VOL:276 PAGE : 41325-41335 (2001)
[TOP]

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