Sphingosine (123-78-4) is an inhibitor of protein kinase C (IC50 = 1-3 μM).1 It is abundant in cell membranes and is an important mediator in various biochemical pathways.2-4
Sphingosine (d18:1) has been used:
- for sphingosine inhalations studies in mice to evaluate its therapeutic potential in respiratory epithelial cells
- to investigate its effect on Pseudomonas aeruginosa strains
- as a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramides
D-erythro-Sphingosine is used to inhibits protein kinase C and calmodulin-dependent enzymes, induces apoptosis. And also used to constituent of cell membranes.
Selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine
cerebroside: Any one of a class ofglycolipids in which a single sugarunit is bound to a sphingolipid. The most commoncerebrosides are galactocerebrosides,containing the sugar group galactose;they are found in the plasma membranesof neural tissue and are abundantin the myelin sheaths ofneurones.
Sphingosine (d18:1) is a spingoid base present in plant and animals. It has 2-amino-1,3-diol functionality and its extraction from animal tissue is laborious. Sphingosine (d18:1) synthesis is performed by chirospecific method using D-galactose.
Inhibitor of protein kinase C and calmodulin-dependent enzymes, but may stimulate mast cells by activation of protein kinase C.
A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinaseA or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.
D-Sphingosine is purified by recrystallisation from EtOAc, Et2O or pet ether (60-80o). It is insoluble in H2O but is soluble in Me2CO, EtOH and MeOH. It has IR bands at 1590 and 875 cm-1, and is characterised as the tribenzoate m 122-123o (from 95% EtOH). [Tipton Biochemical Preparations 9 127 1962.]
[1] JR. A H M. Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds[J]. Biochemistry Biochemistry, 1989, 28 8: 3138-3145. DOI:
10.1021/bi00434a004[2] J OHANIAN V O. Sphingolipids in mammalian cell signalling.[C]//148 1. 2001: 2053-2068. DOI:
10.1007/pl00000836[3] RUVOLO P P. Intracellular signal transduction pathways activated by ceramide and its metabolites[J]. Pharmacological research, 2003, 47 5: Pages 383-392. DOI:
10.1016/s1043-6618(03)00050-1[4] CUVILLIER O. Sphingosine in apoptosis signaling[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2002, 1585 2: Pages 153-162. DOI:
10.1016/s1388-1981(02)00336-0
