C24 Ceramide (d18:1/24:0)
(Synonyms: 十四酰鞘氨醇,C24 Ceramide) 目录号 : GC43074A naturally occurring ceramide
Cas No.:34435-05-7
Sample solution is provided at 25 µL, 10mM.
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- Purity: >98.00%
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Production of ceramide occurs upon hydrolysis of sphingomyelin by a specific isoform of PLC, appropriately named sphingomyelinase.[1] C24 Ceramide (d18:1/24:0) is one of the most abundant naturally occurring ceramides. [2][3][4] Ceramides mediate many diverse biological activities, as has been demonstrated in studies utilizing cell-permeable ceramide analogs. A few of the processes regulated by ceramides include apoptosis, cell differentiation, proliferation of smooth muscle cells, and inhibition of the mitochondrial respiratory chain.[5][6][7]
Reference:
[1]. Perry, D.K., Obeid, L.M., and Hannun, Y.A. Ceramide and regulation of apoptosis and the stress response. Trends in Cardiovascular Medicine 6, 158-162 (1996).
[2]. Gu, Q., Kerwin, J.L., Watts, J.D., et al. Ceramide profiling of complex lipid mixtures by electrospray ionization mass spectrometry. Anal. Biochem. 244(2), 347-356 (1997).
[3]. Clayton, R.B., Cooper, J.M., Curstedt, T., et al. Stimulation of erythroblast maturation in vitro by sphingolipids. J. Lipid Res. 15(6), 557-562 (1974).
[4]. Krivit, W., and Hammarström, S. Identification and quantitation of free ceramides in human platelets. J. Lipid Res. 13(4), 525-530 (1972).
[5]. Testi, R. Sphingomyelin breakdown and cell fate. Trends Biochem. Sci. 21(12), 468-471 (1996).
[6]. Augé, N., Andrieu, N., Nègre-Salvayre, A., et al. The sphingomyelin-ceramide signaling pathway is involved in oxidized low density lipoprotein-induced cell proliferation. J. Biol. Chem. 271(32), 19251-19255 (1996).
[7]. Gudz, T.I., Tserng, K.Y., and Hoppel, C.L. Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide. J. Biol. Chem. 272(39), 24154-24158 (1997).
Cas No. | 34435-05-7 | SDF | |
别名 | 十四酰鞘氨醇,C24 Ceramide | ||
化学名 | N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-tetracosanamide | ||
Canonical SMILES | CCCCCCCCCCCCCCCCCCCCCCCC(N[C@H](CO)[C@@H](O)/C=C/CCCCCCCCCCCCC)=O | ||
分子式 | C42H83NO3 | 分子量 | 650.1 |
溶解度 | Chloroform: slightly soluble; Methanol: slightly soluble | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.5382 mL | 7.6911 mL | 15.3822 mL |
5 mM | 0.3076 mL | 1.5382 mL | 3.0764 mL |
10 mM | 0.1538 mL | 0.7691 mL | 1.5382 mL |
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Plasma levels of ceramides relate to ischemic stroke risk and clinical severity
Brain Res Bull 2020 May;158:122-127.PMID:32165273DOI:10.1016/j.brainresbull.2020.03.009.
Recent studies have suggested that specific plasma ceramides are independently associated with atherosclerosis and cardiovascular diseases, but it is currently unknown whether plasma ceramide levels are associated with ischemic stroke. Here, we examined whether ceramides were associated with both ischemic stroke risk and clinical severity at admission. We measured three previously identified high-risk plasma ceramide molecules [Cer(d18:1/16:0), Cer(d18:1/22:0), and Cer(d18:1/24:0)] in 202 patients with acute ischemic stroke and 202 age and sex matched control cases. Plasma ceramides levels were measured by a targeted liquid chromatography-tandem mass spectrometry assay at baseline. The median age of the 202 stroke patients was 66 (interquartile range [IQR], 58-75) years and 54.0 % were men. Plasma levels of C16:0, C22:0, and C24:0 ceramides in stroke patients were significantly higher than in those control cases (P < 0.001, all). In multivariate logistic regression analysis adjusted for other risk factors, higher levels of C16:0, C22:0, and C24:0 ceramides were associated with higher risk of ischemic stroke (odd ratio [OR] for one IQR increase: 2.15[1.42-2.99]; 2.90[2.13-4.01] and 1.29[1.10-1.69]; respectively). At admission, 103 patients (51.0 %) had a minor stroke (NIHSS < 6). In these patients, plasma levels of C16:0, C22:0, and C24:0 ceramides were lower than that observed in patients with moderate-to-high clinical severity (P < 0.001, all). In multivariate logistic regression analysis adjusted for other risk factors, higher levels of C16:0, C22:0, and C24:0 ceramides were associated with higher risk of moderate-to-high stroke (OR for one IQR increase: 2.96 [2.05-4.22], 3.03 [2.01-4.25] and 1.72 [1.25-3.31], respectively). An elevated plasma levels of ceramides were predictors of both risk and severity at admission in ischemic stroke patients. The underlying mechanisms of these associations remain to be investigated.
Association Between Plasma Ceramides and One-Year Mortality in Patients with Acute Coronary Syndrome: Insight from the PEACP Study
Clin Interv Aging 2023 Apr 6;18:571-584.PMID:37050937DOI:10.2147/CIA.S402253.
Background: The plasma lipidome profile is likely to improve risk stratification in patients with acute coronary syndrome (ACS) and predict cardiovascular events for secondary disease prevention. Ceramides are involved in the initiation or acceleration of several key pathophysiological processes in atherosclerosis. This study evaluated whether plasma ceramide levels at admission was associated with one-year mortality in patients with ACS. Methods: In total, 826 patients with ACS from a prospective multicenter study for early evaluation of acute chest pain were enrolled. High-performance liquid chromatography with tandem mass spectrometry (LC/MS) was used to measure the plasma levels of eleven ceramides (C16-C26). The primary outcome was all-cause mortality, and the secondary outcome was cardiac mortality during the one-year follow-up. The relationship between the ceramide levels and mortality was evaluated by Cox regression analysis. The receiver operating characteristic (ROC) curve was established to evaluate discrimination of ceramides. Results: Eighty-eight (10.7%) patients died after a 12-month follow-up. Five ceramides (C16:0, C18:0, C20:0, C24:1 and C24:2) and their ratios to Cer(d18:1/24:0) were independently associated with the risk of all-cause death and cardiac death. Combining the Global Registry of Acute Coronary Events (GRACE) score with ceramides and their ratios to Cer(d18:1/24:0) had areas under ROC curves ranging from 0.778-0.804 (P<0.001) for all-cause mortality, which was greater than that of the GRACE score alone. Conclusion: Measurements of long-chain ceramides and very-long-chain ceramides may help in identifying a high risk of mortality beyond traditional assessment tools in patients with ACS. Trial registration: clinicaltrials.gov, identifier: NCT04122573.
Ganglioside Composition Distinguishes Anaplastic Ganglioglioma Tumor Tissue from Peritumoral Brain Tissue: Complementary Mass Spectrometry and Thin-Layer Chromatography Evidence
Int J Mol Sci 2021 Aug 17;22(16):8844.PMID:34445547DOI:10.3390/ijms22168844.
Gangliosides serve as antitumor therapy targets and aberrations in their composition strongly correlate with tumor growth and invasiveness. Anaplastic ganglioglioma is a rare, poorly characterized, malignant neuronal-glial tumor type. We present the first comparative characterization of ganglioside composition in anaplastic ganglioglioma vs. peritumoral and healthy brain tissues by combining mass spectrometry and thin-layer chromatography. Anaplastic ganglioglioma ganglioside composition was highly distinguishable from both peritumoral and healthy tissue despite having five to six times lower total content. Ten out of twelve MS-identified ganglioside classes, defined by unique glycan residues, were represented by a large number and considerable abundance of individual species with different fatty acid residues (C16-C24) in ceramide portions. The major structurally identified class was tumor-associated GD3 (>50%) with 11 species; GD3 (d18:1/24:0) being the most abundant. The dominant sphingoid base residue in ganglioside ceramides was sphingosine (d18:1), followed by eicosasphingosine (d20:1). The peritumoral tissue ganglioside composition was estimated as normal. Specific ganglioside composition and large variability of ganglioside ceramide structures determined in anaplastic ganglioglioma demonstrate realistic ganglioside expression patterns and correspond to the profile of high-grade malignancy brain tumors.