Sphingomyelins are complex membrane lipids composed of phosphorylcholine, sphingosine, and an acylated group, such as a fatty acid. Lysosphingomyelin is a naturally-occurring lipid which is produced by the removal of the acylated group of sphingomyelin by a deacylase. Lysosphingomyelin may, in turn, serve as a substrate for autotaxin, which removes choline to produce sphingosine-1-phosphate. The receptors and signaling pathways that are activated by lyso-sphingosine are diverse and vary between cell types. Lysosphingomyelin occurs naturally in plasma, is a constituent of lipoproteins, and is increased in some diseases, including dermatitis and Niemann-Pick disease.

C12 Galactosylceramide is a bioactive sphingolipid. It inhibits IL-4 production by 53.84% in EL4 T cells when used at a concentration of 10 μM. C12 Galactosylceramide reduces the growth of human papillomavirus type 16-associated tumors in mice and reduces tumor recurrence following surgical removal or chemotherapy. It also reduces natural killer T cell activity, delays the onset of proteinuria, and improves survival in a mouse model of systemic lupus.

D-Glucosyl-β-1,1′-N-palmitoylsphingosine (C16 Glucosyl(β) Ceramide (d18:1/16:0)) serves as an endogenous ligand for the Macrophage-Inducible C-type Lectin (Mincle), exhibiting immunostimulatory properties [1].

C22 Glucosylceramide (d18:1/22:0) is an endogenous glucosylceramide. Glucosylceramides are major constituents of skin lipid membranes where they play a role in maintaining the water permeability barrier. They are precursors in the synthesis of lactosylceramide , as well as oligoglycolipids and gangliosides. Phospholipase A2 (PLA2) type XIIA knockdown increases C22 glucosylceramide (d18:1/22:0) expression in rat brain. It is also increased in the brain, but not the liver or spinal cord, of mice fed a methionine-restricted diet. In human athletes, plasma levels of C22 glucosylceramide (d18:1/22:0) increase during exercise and return to basal levels during recovery. This product contains C22 glucosylceramide (d18:1/22:0) isolated from bovine buttermilk.

C17 Ceramide is a synthetic ceramide that contains a non-natural C17:0 fatty acid acylated to sphingosine. It has been used as a marker of arylsulfatase A and sphingolipid activator B activity in patients undergoing enzyme replacement therapy for the genetic disease metachromatic leukodystrophy.

C8 Galactosylceramide is a synthetic C8 short-chain derivative of known membrane microdomain-forming sphingolipids. It increases the amount delivered and toxicity of doxorubicin in cancerous but not non-cancerous cells when incorporated into the nanoliposomal membrane of nanoliposomal-doxorubicin. C8 Galactosylceramide induces proliferation and cytokine production by splenocytes in vitro at concentrations ranging from 100-1,000 ng/ml but has no effect on natural killer T cell production in vivo. It also activates NF-κB production in C6 glioma cells when used at a concentration of 10 μM.

Psychosine (Galactosylsphingosine) is a PKC inhibitor, a substrate for the enzyme galactosylceramide cerebrosidase (GALC), and a potential biomarker of Krabbe's disease.Psychosine is highly cytotoxic and induces cell death in a variety of cells.

C26 Sphingomyelin is a sphingolipid that has been found in serum and cell or brain extracts.1,2,3C26 sphingomyelin levels are increased in the serum of patients with hemophagocytic lymphohistiocytosis, an inflammatory condition characterized by excessive immune activation.3C26 sphingomyelin has been used a component of monolayers to study the influence of sphingomyelin acyl chain length on sphingomyelin-sterol interactions.4[Matreya, LLC.] 1.Wang, J.-R., Zhang, H., Yau, L.D., et al.Improved sphingolipidomic approach based on ultra-high performance liquid chromatography and multiple mass spectrometries with application to cellular neurotoxicityAnal. Chem.86(12)5688-5696(2014) 2.Willmann, J., Mahlstedt, K., Leibfritz, D., et al.Characterization of sphingomyelins in lipid extracts using a HPLC-MS-offline-NMR methodAnal. Chem.79(11)4188-4191(2007) 3.Jenkins, R.W., Clarke, C.J., Lucas, J.T., Jr., et al.Evaluation of the role of secretory sphingomyelinase and bioactive sphingolipids as biomarkers in hemophagocytic lymphohistiocytosisAm. J. Hematol.88(11)E265-E272(2013) 4.Li, X.M., Momsen, M.M., Brockman, H.L., et al.Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranesBiophys. J.85(6)3788-3801(2003)

Lactosylsphingosine is a bioactive sphingolipid and a form of lactosylceramide that is lacking the fatty acyl group. Lyso-lactosylceramide (1-50 μM) reduces viability of human neutrophils in a concentration-dependent manner. Unlike lactosylceramide,lactosylsphingosine has no effect on protein synthesis and cell proliferation in cardiomyocytes. Lactosylsphingosine is a precursor in the synthesis of lyso-ganglioside GM3.

C18 globotriaosylceramide is an endogenous sphingolipid found in mammalian cell membranes that is synthesized from lactosylceramide . It inhibits aggregation of human neutrophils induced by phorbol 12-myristate 13-acetate (PMA; 10008014) when used at a concentration of 1 μM. C18 globotriaosylceramide acts as a receptor for Shiga toxin in B cell-derived Raji cells and THP-1 monocytes. It accumulates in the brain, heart, kidney, liver, lung, and spleen in a mouse model of Fabry disease, a lysosomal storage disorder characterized by a deficiency in the enzyme α-galactosidase A. C18 globotriaosylceramide also accumulates in endothelial cells, pericytes, vascular smooth muscle cells, renal epithelial cells, dorsal ganglia neuronal cells, and myocardial cells in patients with Fabry disease.

C16 Galactosylceramide is a glycosphingolipid that contains a galactose moiety attached to a ceramide acylated with palmitic acid .

C2 Adamantanyl Galactosylceramide (d18:1/2:0) (AdaGalCer) is a bioactive sphingolipid. It reduces globotriaosylceramide 3 synthesis from exogenous lactosylceramide in microsomes. AdaGalCer stimulates recombinant glucocerebrosidase activity in a pH-dependent manner. It activates glucocerebrosidase to decrease glucosylceramide accumulation in fibroblasts and lymphoblasts isolated from patients with Gaucher and Fabry disease, respectively.

C16 globotriaosylceramide is an endogenous sphingolipid found in mammalian cell membranes that is synthesized from C16 lactosylceramide . C16 globotriaosylceramide acts as a receptor for Shiga toxin in B cell-derived Raji cells and THP-1 monocytes. It accumulates in endothelial cells, pericytes, vascular smooth muscle cells, renal epithelial cells, dorsal ganglia neuronal cells, and myocardial cells in patients with Fabry disease. C16 globotriaosylceramide is also upregulated in plasma of patients with ovarian carcinoma compared to those with benign ovarian tumors or uterine fibroids.

C18:1 3'-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It has been found in mouse brain. It has been used as a standard for the quantification of C18:1 3'-sulfo galactosylceramide in dried blood spots from patients with metachromatic leukodystrophy (MLD) by UPLC-MS.

C20 Sphingomyelin is a naturally occurring sphingolipid. Levels of C20 sphingomyelin are upregulated in the hippocampus of rats with diabetes induced by streptozotocin and in human plasma where it is positively correlated with insulin resistance in obese humans. C20 sphingomyelin is also upregulated in the liver of a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder. The plasma concentration of C20 sphingomyelin is decreased in men with prostate cancer.

C22 Galactosylceramide is a sphingolipid that has been found in the central nervous system.1,2C22 Galactosylceramide levels are increased in the spinal cord, but not the brain or liver, of mice fed a methionine-restricted diet.1C22 Galactosylceramide has been found in postmortem hippocampus from patients with Alzheimer's disease.2[Matreya, LLC.]

Lyso-globotriaosylceramide is a form of globotriaosylceramide that is lacking the fatty acyl group. It binds to Shiga toxin 1 (Stx1) in the presence of cholesterol and phosphatidylcholine but does not bind Stx2. It also reduces viability and aggregation of human neutrophils induced by phorbol 12-myristate 13-acetate when used at concentrations of 50 and 1 μM, respectively. Lyso-globotriaosylceramide accumulates in the brain, heart, kidney, liver, lung, and spleen in a mouse model of Fabry disease, a lysosomal storage disorder characterized by a deficiency in the enzyme α-galactosidase A. It also accumulates in the urine, kidney, and plasma of patients with Fabry disease. Lyso-globotriaosylceramide levels decrease in response to administration of the α-galactosidase inhibitor 1-deoxygalactonojirimycin in a transgenic mouse model of Fabry disease. Decreases in plasma and urine concentrations of lyso-globotriaosylceramide have been used as a biomarker for efficacy of enzyme replacement therapy (ERT) and other therapies in the treatment of Fabry disease.

C14 Ceramide (d18:1/14:0) is an endogenous ceramide produced by ceramide synthetase 6, which can be used for Parkinson's research.

1-β-D-Glucosylsphingadienine is a glucosylsphingosine, which are deacetylated lysolipid derivatives of glucosylcerebrosides . They are formed when sphingosines undergo glucosidation by UDP-glucose. Glucosylsphingosines completely reduce neurite outgrowth and induce death of LA-N-2 cells at concentrations of 10 and 50 μM, respectively. They also decrease the activity of glucocerebrosidase in LA-N-2 cells in a dose-dependent manner. Glucosylsphingosine levels are elevated in patients with Gaucher's disease, both in the spleen (in types 1, 2, and 3) and brain (type 2 and 3); thus, glucosylsphingosine has been used as a key biomarker of the disease. This product contains 1-β-D-glucosylsphingadienine isolated from plants.

C17 Globotriaosylceramide is a sphingolipid that has been used as an internal standard for the quantification of globotriaosylceramides in plasma and urine from patients with Fabry disease by GC-MS.

C2 Adamantanyl globotriaosylceramide (AdaGb3) is a bioactive sphingolipid and water-soluble form of globotriaosylceramide that contains an adamantanyl group in place of the fatty acyl chain. It inhibits Vero toxin binding to globotriaosylceramide in an ELISA assay when used at a concentration of 10 μM. AdaGb3 decreases cell surface expression of P-glycoprotein (P-gp) and reduces efflux of rhodamine 123 in MDCK cells. It also increases apical-to-basal transport of vinblastine in human intestinal C2BBe1 cells.

C18 L-threo Ceramide is a synthetic ceramide and stereoisomer of C18 ceramide that has been used for structural characterization of natural sphingolipids. It inhibits rat brain mitochondrial ceramidase (mt-CDase) with an IC50 value of 0.21 mol% (16.8 μM).

C16 Sphingomyelin (d18:1/16:0) (N-Palmitoyl-D-sphingomyelin) is a phospholipid analog of phospholipid bilayer membranes, which can be used to study biofilm activity.

N-Acetylpsychosine, also known as α-galactosylated C2-ceramide (d18:1/2:0), exhibits immunostimulatory properties. This compound, N-Acetylpsychosine, holds potential as a valuable tool for studying the mechanisms of apoptosis and immune responses activated by dendritic cells (DCs).

C2 3'-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It has been used as an internal standard in the quantification of lysosulfatides in mouse brain tissue and plasma.

C18 D-threoCeramide (d18:1/18:0) is a synthetic ceramide and stereoisomer of C18 ceramide .1It inhibits rat brain mitochondrial ceramidase (mt-CDase) with an IC50value of 16.6 μM.2[Matreya, LLC. Catalog No. 1855] 1.Koolath, S., Murai, Y., Suga, Y., et al.Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthaseChirality32(3)308-313(2019) 2.Usta, J., El Bawab, S., Roddy, P., et al.Structural requirements of ceramide and sphingosine based inhibitors of mitochondrial ceramidaseBiochemistry40(32)9657-9668(2001)

C17 Lactosylceramide is a naturally occurring sphingolipid that has been found in human brain metastases of lung adenocarcinomas but not in healthy brain tissue.

C18 3'-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. Levels of short-chain sulfatides, including C18 3'-sulfo galactosylceramide, decrease with age in mice and humans. It is increased in brain from mice with an arylsulfatase A deficiency (ASA-KO), particularly in lipid raft fractions. Plasma levels of C18 3'-sulfo galactosylceramide positively correlate with disability progression in patients with relapsing-remitting multiple sclerosis using the Expanded Disability Status Scale. It is also increased in plasma from patients with metachromatic leukodystrophy (MLD).

EOS is a ceramide found in the outer layer of the epidermis in mammals. It is comprised of an ω-hydroxy very long-chain ceramide (C28-36) esterified to the essential fatty acid linoleic acid . The consecutive regio- and stereospecific oxygenation of the linoleate portion of EOS by 12(R)-lipoxygenase (12(R)-LO) and eLOX3 is essential for the maintenance of the epidermal barrier to prevent water loss. Following oxygenation, the oxidized linoleate is hydrolyzed, leaving the ω-hydroxy end of the very long-chain fatty acid to covalently bind the protein layer, forming the corneocyte lipid envelope and sealing the gap between the extracellular lipid lamellae and the cornified cell envelope of the corneocyte.

Lysosphingomyelin is an endogenous bioactive sphingolipid and a constituent of lipoproteins.1,2It is produced by the removal of the acyl group from sphingomyelin by a deacylase and acts as a precursor in the biosynthesis of sphingosine-1-phosphate . D-erythroLysosphingomyelin is an agonist of the S1P receptors S1P1, S1P2, and S1P3(EC50s = 167.7, 368.1, and 482.6 nM, respectively, for the human receptors).3It is also an agonist of the orphan receptor ovarian cancer G protein-coupled receptor 1 (ORG1) that induces calcium accumulation in cells overexpressing OGR1 (EC50= ~35 nM).4Levels of D-erythrolysosphingomyelin are increased in skin isolated from patients with atopic dermatitis, as well as postmortem brain from patients with Niemann-Pick disease type A, but not type B.2,5L-threolysosphingomyelin is also an S1P1-3agonist (EC50s = 19.3, 131.8, and 313.3 nM, respectively).3This product is a mixture of D-erythroand L-threolysosphingomyelin. [Matreya, LLC. Catalog No. 1321] 1.Ito, M., Kurita, T., and Kita, K.A novel enzyme that cleaves the N-acyl linkage of ceramides in various glycosphingolipids as well as sphingomyelin to produce their lyso formsJ. Biol. Chem.270(41)24370-24374(1995) 2.Nixon, G.F., Mathieson, F.A., and Hunter, I.The multi-functional role of sphingosylphosphorylcholineProg. Lipid Res.47(1)62-75(2008) 3.Im, D.-S., Clemens, J., Macdonald, T.L., et al.Characterization of the human and mouse sphingosine 1-phosphate receptor, S1P5 (Edg-8): Structure-activity relationship of sphingosine1-phosphate receptorsBiochemistry40(46)14053-14060(2001) 4.Meyer zu Heringdorf, D., Himmel, H.M., and Jakobs, K.H.Sphingosylphosphorylcholine-biological functions and mechanisms of actionBiochim. Biophys. Acta1582(1-3)178-189(2002) 5.Rodriguez-Lafrasse, C., and Vanier, M.T.Sphingosylphosphorylcholine in Niemann-Pick disease brain: Accumulation in type A but not in type BNeurochem. Res.24(2)199-205(1999)

C16 Lactosylceramide is an endogenous bioactive sphingolipid. It forms membrane microdomains with Lyn kinase and the αi subunits of inhibitory G protein-coupled receptors (GPCRs), suggesting a role in cell signaling. Plasma levels of C16 lactosylceramide are elevated in insulin-resistant cattle. C16 Lactosylceramide is also upregulated in a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder.

Tetracosanoyl-sulfatide is an endogenous sulfated glycolipid, which are also known as sulfatides . Tetracosanoyl-sulfatide is the major sulfatide in mature myelin in the central and peripheral nervous systems. Levels of Tetracosanoyl-sulfatide are elevated in plasma derived from patients with metachromatic leukodystrophy, a disorder characterized by arylsulfatase A deficiency, leading to sulfatide accumulation. Unlike C24:1 3'-sulfo galactosylceramide, it does not induce an immune response in mouse splenocytes in vitro.

C12-Ceramide (C12 Ceramide (d18:1/12:0)), a ceramide present in the protective membranes surrounding umbilical cord blood vessels in infants born to women with pre-eclampsia, can be used to assess the level of ASM activity in the plasma of patients with Niemann-Pick disease.

C19 Ceramide is a naturally occurring ceramide that has been found in J. juncea extracts as well as rat brain and mouse heart.[1],[2],[3] It is elevated in adult and decreased in juvenile whole rat brain extracts by 114 and 37%, respectively, following chronic ethanol exposure.[2] C19 Ceramide is also increased in mouse hearts following administration of angiotensin II.[3]

BODIPY-C12 Ceramide (B12Cer) is a fluorescently-tagged form of C12 ceramide, with excitation/emission maxima at 505/540 nm, respectively. It is a fluorescently-labeled sphingolipid and has been utilized for quantifying acid sphingomyelinase activity in the plasma of patients with Niemann-Pick disease.

C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) is the predominant sulfate analog in the mature myelin sheath. C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) interacted with C-type lectin and immunoglobulin-like receptors to give the highest affinity for LMIR5. Galactosylceramide (d18:1/24:1(15Z)) induces MCP-1 production by basophils, which activates NFAT by increasing LMIR5, but not mast cells .C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) binds in vitro to CD1d binding and increased the proliferation of free mouse splenocytes.

C6 L-erythro Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It is metabolized by ceramide glucosyltransferase to form C6 L-erythro glucosylceramide. C6 L-erythro Ceramide is cytotoxic to U937 cells (IC50 = 18 μM).

N-Stearoylsphingosine (Cer(d18:1/18:0)) is an amide compound widely found in eukaryotic organisms that enhances protein phosphatase 2A (PP2A) activity by interfering with the binding of PP2A to PP2A inhibitor 2, leading to dephosphorylation of Akt.N-Stearoylsphingosine is used in prostate cancer research.

C8 D-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It is cytotoxic to U937 cells (IC50 = 17 μM) and induces nuclear DNA fragmentation 5- to 6-fold more potently than C8 ceramide . C8 D-threo Ceramide is a substrate for E. coli diacylglycerol kinase. It activates ceramide-activated protein kinase (CAPK) in U937 cells. C8 D-threo Ceramide also enhances V. cholerae cytolysin pore formation in liposome lipid membranes, as measured by calcein release, with a 50% release dose (RD50) value of ~5 μg/ml.

C4 Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. [1] [2] [3] It inhibits IL-4 production by 16% in EL4 T cells stimulated with phorbol 12-myristate 13-acetate when used at a concentration of 10 μM. [1] C4 Ceramide is cytotoxic to SK-BR-3 and MCF-7/Adr breast cancer cells (IC50s = 15.9 and 19.9 μM, respectively). [2] C4 Ceramide also increases maturation and stability of cystic fibrosis transmembrane conductance regulator (CFTR) proteins bearing the F508 deletion (F508del) mutation, enhances cAMP-activated chloride secretion, and suppresses secretion of IL-8 in primary epithelial cells isolated from patients with cystic fibrosis.[3]

C16 3'-sulfo Galactosylceramide (d18:1/16:0) is a sulfated glycolipid.C16 3'-sulfo Galactosylceramide (d18:1/16:0) is a relatively abundant sulfide found in porcine brain and plasma that decreases throughout development in mice.C16 3'-sulfo Galactosylceramide is a relatively abundant sulfide found in porcine brain and plasma that decreases throughout development in mice.C16 3'-sulfo Galactosylceramide is a relatively abundant sulfide found in porcine brain and plasma that decreases throughout development in mice. C16 3'-sulfo Galactosylceramide (d18:1/16:0) inhibits retinal ganglion cell growth in vitro.C16 3'-sulfo Galactosylceramide (d18:1/16:0) has been used as an internal standard for quantifying C16 3'-sulfo Galactosylceramide (d18:1/16:0) in rat cerebellum and white matter isolated from patients with multiple sclerosis. reference for sulphides.

C18 L-erythro Ceramide (d18:1/18:0) significantly reduced extracellular Aβ levels and can be used to study Alzheimer's disease.

C18 Ceramide-1-phosphate (d18:1/18:0) is a long-chain molecule identified in murine skin known to promote the migration of mouse bone marrow-derived multipotent stromal cells and human umbilical vein endothelial cells (HUVECs) at concentrations of 0.5 to 5 µM. It exhibits elevated levels in CFPAC-1 pancreatic ductal adenocarcinoma cells compared to pancreatic cancer stem cells, and its myocardial concentration is heightened in Langendorff isolated perfused mouse hearts under an ex vivo ischemia model.