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Sphingolipid Metabolism

Sphingolipids contain a lipophilic long-chain amino alcohol like sphingosine, dihydrosphingosine, phytosphingosine, or dehydrophytosphingosine as the characteristic polyalcohol constituent. Sphingosine or a related base is bound to a long-chain fatty acid by an amide linkage and via the terminal hydroxyl group to either a complex carbohydrate or phosphorus-containing moiety. Cerebrosides, sulfatides, ceramide-polyhexosides, and gangliosides are glycosphingolipids, i.e., contain a carbohydrate component instead of phosphorylcholine. The carbohydrate moiety of a glycosphingolipid is oriented towards the exterior cell membrane surface and is characteristic for the cell type, species, growth phase, and differentiated/undifferentiated status.

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S7049 D-Sphingosine synthetic A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.
Natural isomer of sphingosine
C8355 D-erythro-Ceramide C8 1-phosphate ≥93% (TLC), solid Cell permeable stimulator of DNA synthesis in cultured fibroblasts; antagonizes mitogenic activity.
D3439 D-erythro-Dihydrosphingosine 1-phosphate ≥98% (TLC), waxy solid Negative control for sphingosine-1-phosphate.
D3314 D-erythro-Dihydrosphingosine ≥98% Biosynthetic precursor to sphingosine; inhibits protein kinase C.
D4556 D-threo-Dihydrosphingosine  
D6783 DL-Dihydrosphingosine ≥98%, synthetic Biosynthetic precursor of sphingosine.
D6908 DL-erythro-Dihydrosphingosine ≥99%, synthetic D-Isomer is the biosynthetic precursor of sphingosine; inhibits protein kinase C, phospholipase A2, and phospholipase D.
D7033 DL-threo-Dihydrosphingosine ≥98% Sphingosine kinase inhibitor.
D4681 L-threo-Dihydrosphingosine ≥95% (TLC) Sphingosine kinase inhibitor; protein kinase C alpha (PKCα) -specific inhibitor; Sphingosine analog; potentiates the effect of doxorubicin (DOX) in tumor-bearing animals.
G9398   Asialoganglioside-GM2 from bovine brain ~95%, lyophilized powder Degraded form of Asialoganglioside-GM1 ganglioside.
C4832 Ceramide 1-phosphate from bovine brain ~95% Putative second messenger of agonist-stimulated sphingomyelin metabolism; may participate in cell regulation and transmembrane signaling.
22244 Ceramide from bovine spinal cord ≥98.0% (TLC) Ceramide is a minor component of cell membranes. Activates atypical protein kinase C (e.g., PKCzeta) .
C4987 Ceramide phosphorylethanolamine ≥98% (TLC) Sphingolipid with ethanolamine base, found in insect membranes.
C7980 Dihydroceramide C2 ≥98% (TLC), solid Inactive form of C2 ceramide; may be used as a negative control.
C8230 Dihydroceramide C6 solid Inactive form of C6 ceramide for use as a negative control.
C8605 Dihydroceramide C8 98%, waxy solid Inactive form of C8 ceramide for use as a negative control.
G2392   Disialoganglioside GD1a from bovine brain ≥95% (TLC), lyophilized powder The major ganglioside in brain. Converted to GM1 by bacterial and mammalian sialidase. Differentiation marker for cell growth.
G8146   Disialoganglioside GD1b from bovine brain ~95%, lyophilized powder May act as a bacterial toxin receptor (tetanus, botulinus); high levels found in gliomas and astrocytomas.
G0776   Disialoganglioside-GD2 from bovine brain ~95%, lyophilized powder, semisynthetic Cell surface component from disialoganglioside-GD1b.
C4905 Galactocerebrosides from bovine brain ≥97% (TLC) Galactose linked to ceramide by a β-glycosidic linkage; the major lipid in adult brain, representing approximately 16% of total lipid; they are mainly localized to myelin and are markedly reduced in demyelinating diseases.
C3166   Lactocerebrosides from bovine brain ≥93%  
G7641   Monosialoganglioside GM1 from bovine brain ≥95%, lyophilized powder  
G9652   Monosialoganglioside GM1 from bovine brain lyophilized powder, BioXtra, γ-irradiated, ≥95% (TLC) Monosialoganglioside GM1 is a major sialoglycolipid of neuronal membranes that modulates calcium homeostasis. It binds to cholera toxin B subunit, resulting in stimulation of adenylate cyclase in a wide variety of cell types. After cholera toxin binds to membrane associated monosialoganglioside GM1, the A subunit of cholera toxin is translocated to the cell interior, where it catalyzes the ADP ribosylation of the membrane associated Gs subunit of adenylate cyclase. In addition, binding of cholera toxin to monosialoganglioside GM1 causes translocation of NF-κB and activation of dendritic cells.

Monosialoganglioside GM1 was one of many mono- and oligosaccharide ligands studied for their affinity for NKR-P1, a membrane protein on natural killer cells, which contains an extracellular Ca2+-dependent lectin domain. Monosialoganglioside GM1 is effective in partially correcting the consequences of neuroinjury in a number of in vivo and in vitro model systems.
G8397   Monosialoganglioside GM2 from bovine brain ≥95% (TLC) Minor component of cell membranes that has been shown to accumulate in Tay-Sachs disease.
G5642   Monosialoganglioside GM3 from canine blood ≥98%, lyophilized powder Monosialoganglioside-GM3 is the most common ganglioside and the major ganglioside in non-neuronal cell membranes. It inhibits epidermal cell growth and is involved in the biosynthesis and metabolism of all higher gangliosides.
A7191 N-Acetyl-D-sphingosine ≥97% (TLC), powder Cell-permeable, biologically active ceramide. It induces differentiation and apoptosis in cells and has been shown to activate protein phosphatases.
H6524 N-Hexanoyl-D-sphingosine ≥98% (TLC), synthetic Cell-permeable analog of ceramide; stimulates protein phosphatase 2A; activates MAP kinase; induces apoptosis in human leukemia HL-60 cells
O1882 N-Octanoyl-D-sphingosine waxy solid Synthetic anaolgue of natural ceramide, activates protein kinase C, stimulates IL-2 production and induces apoptosis.
C8105 Phytoceramide C2 98% (TLC) Yeast growth inhibitor and ceramide-activated protein phosphatase (CAPP) activator.
P2795 Phytosphingosine hydrochloride ≥98%, from Saccharomyces cerevisiae Green Alternative Phytosphingosine is a long chain sphingoid base that occurs broadly in yeast, plants and animals including mammals. In yeast it is involved in mediating the heat stress response, perhaps through activation of the AGC-type protein kinases, Pkh1, Pkh2, Ypk1, Ypk2, and Sch9. It is proapoptotic in human cancer cell lines. PHS induces ΔΨm and release of cytochrome c from mitochondria either directly or through activation of p38 MAPK pathway. This leads to activation of caspase 9 followed by activation of caspase 3 and programmed cell death.
P9256 Psychosine from bovine brain lyophilized powder, ≥98% (TLC) Glycolipid precursor of cerebrosides
S5696 SKI II ≥98% (HPLC), solid Sphingosine kinase (SK) plays a pivotal role in regulating tumor growth and SK can act as an oncogene. Expression of SK RNA is significantly elevated in a variety of solid tumors, compared with normal tissue from the same patient. A number of novel inhibitors of human SK were identified, and several representative compounds were characterized in detail. These compounds demonstrated activity at sub- to micromolar concentrations, making them more potent than any other reported SK inhibitor, and were selective toward SK compared with a panel of human lipid and protein kinases. Kinetic studies revealed that the compounds were not competitive inhibitors of the ATP-binding site of SK. 4-[4-(4-chloro-phenyl)-thiazol-2-ylamino]-phenol (SKI-II) inhibitor is orally bioavailable, detected in the blood for at least 8 h, and showed a significant inhibition of tumor growth in mice with IC50 = 0.5 μM; SKI II does not act at ATP-binding site. Displays no inhibition of ERK2, PI 3-kinase, or PKCa at concentrations up to 60 μM.SKI II induces apoptosis and inhibits proliferation in several other tumor cell lines in vitro (IC50 = 0.9-4.6 μM).
S0756 Sphingomyelin from chicken egg yolk, ≥95% Sphingomyelin is the second most abundant lipid and major sphingolipid component of HDL and the plasma membrane. It forms cholesterol-enriched lipid rafts. It has a key role in the availability of plasma membrane-free cholesterol.
S9666 Sphingosine 1-phosphate ≥95%, powder A lipid second messenger that binds to S1P1 and S1P3 receptors. Mobilizes intracellular Ca2+ stores and decreases cellular cAMP. Activates phospholipase D. S1P stimulates the migration of endothelial cells but inhibits the migration of other cell types. Induces angiogenesis.
S4257 Sphingosylphosphorylcholine ≥98%, powder Sphingosylphosphorylcholine (SPC) is a bioactive lipid that mediates intracellular and extracellular signaling. It mobilizes Ca2+ from intracellular stores via an IP3-independent pathway. It stimulates the production of CCL2 that may contribute to development of atherosclerosis. SPC is a ligand for endothelial differentiation gene receptor 3 (EDG3).
S1006   Sulfatides from bovine brain  
G3767   Trisialoganglioside-GT1b from bovine brain lyophilized powder, ≥96% (TLC) Ganglioside marker for metastatic brain tumors. Modulates cellular differentiation; prevents glutamate neurotoxicity; inhibits mitogenesis stimulated by lectins such as Con A. Converted to GD1b by bacterial and mammalian sialidases.