Sphingoid Bases

Sphingosine-1-phosphate (S1P) is an agonist of S1P_1-5 receptors and a ligand of GPR3, GPR6 and GPR12. Sphingosine-1-phosphate is an intracellular second messenger and mobilizes Ca²⁺ as an extracellular ligand for G protein-coupled receptors. Sphingosine-1-phosphate is an important lipid mediator generated from Sphingomyelin (HY-113498) or other membrane phospholipids. Sphingosine-1-phosphate stimulates the DNA synthesis, cell proliferation and migration.

Myriocin (Thermozymocidin), a fungal metabolite could be isolated from Myriococcum albomyces, Isaria sinclairi and Mycelia sterilia, is a potent inhibitor of serine-palmitoyl-transferase (SPT) and a key enzyme in de novo synthesis of sphingolipids. Myriocin suppresses replication of both the subgenomic HCV-1b replicon and the JFH-1 strain of genotype 2a infectious HCV, with an IC₅₀ of 3.5 μg/mL for inhibiting HCV infection.

D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC₅₀ of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator.

Fumonisin B1 is a mycotoxin produced from Fusarium moniliforme. Fumonisin B1 is a potent inhibitor of sphingosine N-acyltransferase (ceramide synthase) and disrupts de novo sphingolipid biosynthesis. Fumonisin B1 is the most abundant and toxic fumonisin.

Phytosphingosine is a phospholipid with anti-inflammatory, antibacterial, and anti-cancer activities, which can induce apoptosis. Phytosphingosine is an immune regulator and can be used in the study of inflammatory skin diseases. Phytosphingosine is also an activator of GPR120 with an IC₅₀ value of 33.4 μM and can be used in the study of type II diabetes.

N,N-Dimethylsphingosine is a sphingosine kinase inhibitor. N,N-Dimethylsphingosine binds competitively to sphingosine kinase and blocks the conversion of sphingosine to sphingosine-1-phosphate. N,N-Dimethylsphingosine inhibits sphingosine-1-phosphate release and aggregation of platelets, and also exerts pro-apoptotic effects by resetting ceramide/sphingosine-1-phosphate homeostasis. N,N-Dimethylsphingosine can be used in cancer-related research.

Lactosylceramide (bovine buttermilk) (LacCer (bovine buttermilk)) is a sphingolipid that highly expressed on the plasma membranes of human phagocytes. Lactosylceramide mediates phagocytosis, chemotaxis, and superoxide generation.

GD1b Sphingosine (d18:1) is a precursor to the GD1b ganglioside.

D-Erythro-dihydrosphingosin directly inhibits cytosolic phospholipase A₂α (cPLA₂α) activity.

W146 is a selective antagonist of sphingosine-1-phosphate receptor 1 (S1PR1) with an EC₅₀ value of 398 nM.

Sphingosylphosphorylcholine is a bioactive lipid and a major component of plasma high-density lipoprotein that binds to OGR1 with a K_d of 33.3 nM. Sphingosylphosphorylcholine triggers delayed phosphorylation of Smad2, upregulates α-SMA expression, and activates TRPM3. Sphingosylphosphorylcholine reduces Apoptosis and upregulates the expression of uPA and its receptor uPA-R. Sphingosylphosphorylcholine exerts anti-apoptotic, anti-cardiac hypertrophy and pro-wound healing effects. Sphingosylphosphorylcholine induces scratching behavior in mice. Sphingosylphosphorylcholine is used in studies related to atopic dermatitis, promyelocytic leukemia, heart failure, myocardial ischemia/reperfusion injury, ovarian cancer, breast cancer, pancreatic cancer, and skin wound healing disorders in genetically impaired healing diabetes.

Sphinganine 1-phosphate (D-erythro-Dihydrosphingosine 1-phosphate) is a polar sphingolipid metabolite that regulates cell migration, differentiation, survival and complex physiological processes.

Sphingosine (d17:1) is a 17-carbon sphingosine found in human skin.

Spisulosine (ES-285) is an antiproliferative (antitumoral) compound of marine origin. Spisulosine inhibits the growth of the prostate PC-3 and LNCaP cells through intracellular ceramide accumulation and PKCζ activation. Spisulosine induces apoptosis in PC-3 and LNCaP cells.

W146 TFA is a selective antagonist of sphingosine-1-phosphate receptor 1 (S1PR1) with an EC₅₀ value of 398 nM.

Fumonisin B2 is a selective ceramide synthase inhibitor and carcinogenic mycotoxin with toxicity comparable to that of Fumonisin B1 (HY-N6719). Fumonisin B2 inhibits de novo sphingolipid biosynthesis by blocking the amide bond formation between fatty acids and dihydrosphingosine, which leads to a massive intracellular accumulation of free dihydrosphingosine, altered sphingosine levels, subsequent inhibition of cell proliferation, and induction of cell death. Fumonisin B2 is used to investigate the pathogenesis of diseases associated with Fusarium verticillioides contamination, including equine leukoencephalomalacia, porcine pulmonary edema syndrome, human esophageal cancer, and rat hepatocellular carcinoma.

Sphingosine-1-phosphate d17:1 (D-erythro-Sphingosine-C17-1-phosphate) is a derivative of ceramide. Sphingosine-1-phosphate d17:1 can be used for the research of cancer.

Sphinganine-C17 (Heptadecasphinganine) is a synthetic bioactive sphingolipid and an isomer of sphinganine. Sphinganine-C17 inhibits the growth of Candida glabrata and Candida albicans with a minimum bactericidal concentration (MBC) of 0.5 μg/mL for both. Sphinganine-C17 can be used as an internal standard for the chromatographic analysis of sphingosine compounds.

Tetraacetylphytosphingosine is a sphingolipid metabolite produced by phytosphingosine acetylation. Tetraacetylphytosphingosine exerts its inhibitory action on angiogenesis through the inhibition of MAPK activation and intracellular calcium increase. Tetraacetylphytosphingosine induces apoptosis in HaCaT cells.

DL-Erythro/threo Sphinganine (d16:0) is an ester product.