N-Eicosanoyl-D-erythro-sphingosylphosphorylcholine Reference: M1917-500 Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis.1 An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease2 and neonatal respiratory distress syndrome.3 However, the ratio of sphingomyelin to ceramide is different for different cell types.4 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.5 N-hexanoyl-sphingosylphosphorylcholine has been used to enhance the uptake of anti-tumor drugs by cancer cells, thereby increasing the cytotoxicity towards those cancer cells.6
N-Docosanoyl-D-erythro-sphingosylphosphorylcholine Reference: M1918-500 Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis.1 An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease2 and neonatal respiratory distress syndrome.3 However, the ratio of sphingomyelin to ceramide is different for different cell types.4 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.5 N-hexanoyl-sphingosylphosphorylcholine has been used to enhance the uptake of anti-tumor drugs by cancer cells, thereby increasing the cytotoxicity towards those cancer cells.6
N-Tetracosenoyl-(cis-15)-D-erythro-sphingosine Reference: M1930-5 Ceramide is a fatty acid amide of sphingosine. This product is a well-defined ceramide with a tetracosenoyl (nervonyl) acyl group. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity. Ceramides with short side chains have been shown to enter easily into cells where they are biologically active while ceramides with longer side chains will enter cells if dissolved in dodecane-isopropanol. Nervonic acid has been found to be important in the biosynthesis of nerve cell myelin and is found in sphingolipids of white matter. There is a marked reduction in the level of nervonic acid in sphingolipids in diseases involving demyelinateion, such as adrenoleukodystropy and multiple sclerosis.4
N-Tetracosenoyl-(cis-15)-sulfatide Reference: M1931-1 Sulfatide is a type of sulfolipid that is found primarily in the central nervous system and is a myelin-specific sphingolipid. A deficiency of sulfatide in white and gray matter has been associated with Alzheimer’s disease and other types of dementia. Apoliprotein E plays an important regulating role in the metabolism of sulfatides.1 A production of anti-sulfatide antibodies in the cerebrospinal fluid, leading to a deficiency in sulfatides, may be a cause of degeneration of the myelin sheath, leading to multiple sclerosis.2 Metachromatic leukodystrophy is an inherited disorder characterized by a deficiency of the lysosomal enzyme arylsulfatase A and the subsequent accumulation of sulfatide in neural and visceral tissues.3 An immunomodulatory role for sulfatides has been suggested in the pathogenesis of tuberculosis. Sulfatides decrease the in vitro production of proinflammatory cytokines. Tetracosenoyl sulfatide has been found to be a major immunodominant specie in myelin. This has important implications for the design of therapeutics that target T cells reactive for myelin glycolipids in autoimmune diseases of the central nervous system.4 Tetracosenoyl sulfatide has also been demonstrated to reverse ongoing chronic and relapsing experimental autoimmune encephalomyelitis in mice.5
N-Octadecanoyl-sulfatide Reference: M1932-1 This product is a well-defined sulfatide containing an octadecanoyl group acylated to the amine of the sphingosine and is ideal as an internal standard. Sulfatide is a type of sulfolipid that is found primarily in the central nervous system and is a myelin-specific sphingolipid. A deficiency of sulfatide in white and gray matter has been associated with Alzheimer’s disease and other types of dementia. Apoliprotein E plays an important regulating role in the metabolism of sulfatides.1 The production of anti-sulfatide antibodies in the cerebrospinal fluid, leading to a deficiency in sulfatides, may be a cause of degeneration of the myelin sheath, leading to multiple sclerosis and other demyelinating diseases.2 Metachromatic leukodystrophy is an inherited disorder characterized by a deficiency of the lysosomal enzyme arylsulfatase A and the subsequent accumulation of sulfatide in neural and visceral tissues.3 Sulfatide also regulates the differentiation of oligodendroblasts. Central nervous system (CNS) myelin is strongly inhibitory to growing axons and sulfatides present in the myelin of the CNS have been identified as major myelin-associated axon growth inhibitors.4 A low level of serum sulfatides has been linked with an increased risk of cardiovascular disease in some situations. Sulfatides in the myelin, especially cistetracosenoyl- sulfatides, stimulate a distinct population of CD1d-restricted natural killer T cells giving these sulfatides important implications for the design of therapeutics that target T cells reactive for myelin glycolipids in autoimmune diseases of the central nervous system.5
N-Octadecenoyl-(cis-9)-sulfatide Reference: M1933-1 This product is a well-defined sulfatide containing an octadecenoyl group acylated to the amine of the sphingosine and is ideal as an internal standard. Sulfatide is a type of sulfolipid that is found primarily in the central nervous system and is a myelin-specific sphingolipid. A deficiency of sulfatide in white and gray matter has been associated with Alzheimer’s disease and other types of dementia. Apoliprotein E plays an important regulating role in the metabolism of sulfatides.1 The production of anti-sulfatide antibodies in the cerebrospinal fluid, leading to a deficiency in sulfatides, may be a cause of degeneration of the myelin sheath, leading to multiple sclerosis and other demyelinating diseases.2 Metachromatic leukodystrophy is an inherited disorder characterized by a deficiency of the lysosomal enzyme arylsulfatase A and the subsequent accumulation of sulfatide in neural and visceral tissues.3 Sulfatide also regulates the differentiation of oligodendroblasts. Central nervous system (CNS) myelin is strongly inhibitory to growing axons and sulfatides present in the myelin of the CNS have been identified as major myelin-associated axon growth inhibitors.4 A low level of serum sulfatides has been linked with an increased risk of cardiovascular disease in some situations. Sulfatides in the myelin, especially cistetracosenoyl- sulfatides, stimulate a distinct population of CD1d-restricted natural killer T cells giving these sulfatides important implications for the design of therapeutics that target T cells reactive for myelin glycolipids in autoimmune diseases of the central nervous system.5
N-Nonadecanoyl-sulfatide Reference: M1935-1 This product is a well-defined sulfatide containing a nonadecanoic fatty acid acylated to the amine of the sphingosine making it ideal as an internal standard. Sulfatide is a type of sulfolipid that is found primarily in the central nervous system and is a myelin-specific sphingolipid. A deficiency of sulfatide in white and gray matter has been associated with Alzheimer’s disease and other types of dementia. Apoliprotein E plays an important regulating role in the metabolism of sulfatides.1 The production of anti-sulfatide antibodies in the cerebrospinal fluid, leading to a deficiency in sulfatides, may be a cause of degeneration of the myelin sheath, leading to multiple sclerosis and other demyelinating diseases.2 Metachromatic leukodystrophy is an inherited disorder characterized by a deficiency of the lysosomal enzyme arylsulfatase A and the subsequent accumulation of sulfatide in neural and visceral tissues.3 Sulfatide also regulates the differentiation of oligodendroblasts. Central nervous system (CNS) myelin is strongly inhibitory to growing axons and sulfatides present in the myelin of the CNS have been identified as major myelin-associated axon growth inhibitors.4 A low level of serum sulfatides has been linked with an increased risk of cardiovascular disease in some situations. Sulfatides in the myelin, especially cistetracosenoyl- sulfatides, stimulate a distinct population of CD1d-restricted natural killer T cells giving these sulfatides important implications for the design of therapeutics that target T cells reactive for myelin glycolipids in autoimmune diseases of the central nervous system.5
N-Dodecanoyl-D-erythro-sphingosine Reference: M1936-10 This N-Dodecanoyl-D-erythro-sphingosine is ideal as a standard and for biological studies. Ceramide is a fatty acid amide of sphingosine that has many important biological functions and is the precursor for many complex glycosphingolipids. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity. In contrast to long chain ceramides short chain ceramides, such as N-octanoyl-sphingosine, can pass thru the cell membrane. This allows short chain ceramides to be used to induce apoptisis or necrosis in cancer cells.4
N-Dodecanoyl-beta-D-galactosylceramide Reference: M1937-10 This cerebroside product is a glycosphingolipid containing a galactose (galactocerebroside) attached to a ceramide acylated with dodecanoic acid. Galactocerebrosides are found primarily in neuronal tissues and are the major glycosphingolipids in the central nervous system. They are the largest single component of the myelin sheath of nerves and seem to act, along with other molecules, to form part of the structural support of the myelin sheath.1 Cerebrosides are involved in a very wide range of biological activities such as cell agglutination, intracellular communication, cellular development, and antitumor/cytotoxic effects.2 Galactocerebroside can be metabolized into sulfatide which is also abundant in the nervous system and myelin sheath. Due to the relatively high melting point of cerebrosides (much greater than physiological body temperature) they have a para-crystalline structure. Krabbe’s disease (globoid cell leukodystrophy) is characterized by a deficiency in the enzyme galactocerebrosidase, which is responsible for degrading galactocerebroside. This leads to an accumulation of cerebroside and psychosine (which is very cytotoxic and can result in demyelination of nerves and loss of axonal conductivity). This standard from Matreya is excellent for use in the identification and isolation of cerebrosides in the study of Krabbe’s disease and other studies.3
N-Octadecenoyl-(cis-9)-D-erythro-sphingosine Reference: M1939-25 This product is a well-defined ceramide containing oleic acid acylated to the sphingosine base making it ideal as a standard and for biological studies. N-Octadecenoyl-(cis-9)-D-erythro-sphingosine has been used in the study of neural progenitor motility regulation and brain development. It was found that ceramide can stimulate migration of neural progenitors in scratch (wounding) migration assays and that sphingolipid depletion leads to ectopic localization of mitotic or post-mitotic neural cells in the embryonic brain.1 Ceramide is a fatty acid amide of sphingosine that has many important biological functions and is the precursor for many complex glycosphingolipids. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity.
N-Octadecenoyl-(cis-9)-D-erythro-sphingosine Reference: M1939-5 This product is a well-defined ceramide containing oleic acid acylated to the sphingosine base making it ideal as a standard and for biological studies. N-Octadecenoyl-(cis-9)-D-erythro-sphingosine has been used in the study of neural progenitor motility regulation and brain development. It was found that ceramide can stimulate migration of neural progenitors in scratch (wounding) migration assays and that sphingolipid depletion leads to ectopic localization of mitotic or post-mitotic neural cells in the embryonic brain.1 Ceramide is a fatty acid amide of sphingosine that has many important biological functions and is the precursor for many complex glycosphingolipids. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity.
Cholesterol-beta-D-glucoside Reference: M1940-5 The physiological significance of the glucosylation of cholesterol is to render cholesterol far more water soluble and usable for transportation within a cell.1 Parkinsonism and glucosylceramide metabolism appear to be linked given the high incidence of neurodegenerative conditions in patients with Gaucher disease, a lysosomal storage disorder.2 It may be speculated that glucosylceramide acts as a donor in the biosynthesis of the potentially neurotoxic steryl-β-glucosides, implying that cholesteryl-β-glucoside is a missing link between parkinsonism and Gaucher.3