N,N-dimethyl Sphinganine (d18:0) is a sphingolipid that increases during development ofL. donovanipromastigotes.1 1.Silva, A.M., Cordeiro-da-Silva, A., and Coombs, G.H.Metabolic variation during development in culture of Leishmania donovani promastigotesPLoS Negl. Trop. Dis.5(12)e1451(2011)
D-threo Sphinganine (d18:0) is a synthetic bioactive sphingolipid and stereoisomer of sphinganine (d18:0) and L-erythro sphinganine (d18:0) . It induces autophagy in HCT116 cells when used at a concentration of 12 μM. D-threo Sphinganine (d18:0) is metabolized via sphinganine N-acyltransferase and sphinganine kinase in vivo in rat liver.
C18 dihydro Ceramide is a bioactive sphingolipid and precursor in the de novo synthesis of C18 ceramide that lacks the 4,5-trans double bond. [1] Increased C18 dihydroceramide lipid levels lead to increased triacylglycerol storage and autophagosome accumulation as well as upregulation of the fibrosis markers α-SMA and FGF2 in Chang and LX-2 liver cells. C18 dihydro Ceramide is elevated in the plasma of pre-diabetics up to 9 years prior to the onset of type 2 diabetes. [2] It is also elevated in the skin of patients with lesional atopic dermatitis.[3]
C24 dihydro Ceramide is a sphingolipid that has been found in the stratum corneum of human skin.[1] It is found in higher concentrations in female sebum compared to male sebum.[2] C24 dihydro Ceramide levels positively correlate with cytotoxicity in CCRF-CEM, MOLT-4, COG-LL-317h, and COG-LL-332h T cell acute lymphoblastic leukemia (ALL) cell lines.[4] Levels of C24 dihydro ceramide are increased by 149.49-fold in dihydroceramide desaturase 1 (DEGS1) knockdown UM-SCC-22A human head and neck squamous carcinoma cells in vitro.[4] C24 dihydro Ceramide levels are also increased in INS-1 β-cells incubated with glucose and palmitate.[5]
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.
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.
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]
C2 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It stimulates cholesterol efflux in CHO cells expressing the human ABCA1 receptor when used at a concentration of 10 μM, however, this efflux is 50% less than that stimulated by C2 ceramide . C2 L-threo Ceramide inhibits IL-4 production by 17% in EL4 T cells stimulated with phorbol 12-myristate 13-acetate when used at a concentration of 10 μM. It also induces cell cycle arrest in the G0 G1 phase and a 7-fold increase in sphingosine accumulation as well as inhibits growth of HL-60 leukemia cells.
13C C16 Sphingomyelin is an isotopically enriched form of C16 sphingomyelin with carbon-13 occurring on the fatty acid portion. It is intended for use as an internal standard for the quantification of C16 sphingomyelin by GC- or LC-MS. C16 Sphingomyelin is a form of sphingomyelin containing palmitate (16:0) at the variable acylation position. It is the most common form of sphingomyelin found in eggs and is less abundant in the brain and in milk. C16 Sphingomyelin interacts with cholesterol in ordered lipid domains (lipid rafts). Sphingomyelinases remove phosphorylcholine from C16 sphingomyelin to produce C16 ceramide. While ceramides commonly induce apoptosis, ceramides with different fatty acid chain lengths might direct distinct functions and, in some cases, reduce apoptosis.
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).
C6 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides., C6 L-threo Ceramide is cytotoxic to U937 cells in vitro (IC50 = 18 μM). It is metabolically inactive and, unlike C6 L-erythro ceramide , C6 L-threo ceramide cannot be converted to C6 glucosylceramide by ceramide glucosyltransferase. C6 L-threo Ceramide enhances IL-4 production induced by phorbol 12-myristate 13-acetate in EL4 T cells when used at a concentration of 10 μM.
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.
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.
C8 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It is cytotoxic to U937 cells (IC50 = 10 μM) and, like C8 D-threo ceramide , induces nuclear DNA fragmentation 5- to 6-fold more potently than C8 L-erythro ceramide . 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 ~30 μg ml.
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.