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Sphingosine-13C2-d2 (d18:1)

(Synonyms: D-erythro-Sphingosine C18-13C2-d2) 目录号 : GC48089

A neuropeptide with diverse biological activities

Sphingosine-13C2-d2 (d18:1) Chemical Structure

Cas No.:2692623-81-5

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1 mg
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产品描述

Sphingosine-13C2-d2 (d18:1) is intended for use as an analytical standard for the quantification of sphingosine (d18:1) by GC- or LC-MS. Sphingosine (d18:1) is formed primarily from the breakdown of ceramide.1 Sphingosine (d18:1) inhibits protein kinase C and phosphatidic acid phosphohydrolase, whereas it activates phospholipase D and diacylglycerol (DAG) kinase.1 Phosphorylation of sphingosine (d18:1) by sphingosine kinases 1 and 2 (SPHK1, SPHK2) produces sphingosine-1-phosphate, a potent bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization, and morphogenesis.2,3,4

1.Hannun, Y.A., Luberto, C., and Argraves, K.M.Enzymes of sphingolipid metabolism: From modular to integrative signalingBiochemistry40(16)4893-4903(2001) 2.Takuwa, Y., Takuwa, N., and Sugimoto, N.The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activitiesJ. Biochem.131(6)767-771(2002) 3.Ishii, I., Fukushima, N., Ye, X., et al.Lysophospholipid receptors: Signaling and biologyAnnu. Rev. Biochem.73321-354(2004) 4.Kluk, M.J., and Hla, T.Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptorsBiochim. Biophys. Acta1582(1-3)72-80(2002)

Chemical Properties

Cas No. 2692623-81-5 SDF
别名 D-erythro-Sphingosine C18-13C2-d2
Canonical SMILES O[13C]([2H])([2H])[13C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC
分子式 C16[13C]2H35D2NO2 分子量 303.5
溶解度 Chloroform: soluble,Methanol: soluble 储存条件 Store at -20°C
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10 mM 0.3295 mL 1.6474 mL 3.2949 mL
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Research Update

Sphingomyelin SM(d18:1/18:0) is significantly enhanced in cerebrospinal fluid samples dichotomized by pathological amyloid-β42, tau, and phospho-tau-181 levels

J Alzheimers Dis 2015;44(4):1193-201.PMID:25408209DOI:10.3233/JAD-142319.

Alzheimer's disease (AD) is a severe and chronic neurodegenerative disorder of the brain. The laboratory diagnosis is limited to the analysis of three biomarkers in cerebrospinal fluid (CSF): amyloid-β42 (Aβ42), total tau, and phospho-tau-181 (P-tau-181). However, there is a need to find more biomarkers in CSF that can improve the sensitivity and specificity. The aim of the present study was to analyze endogenous small metabolites (metabolome) in the CSF, which may provide potentially new insights into biochemical processes involved in AD. One hundred CSF samples were dichotomized by normal (n = 50) and pathological decreased Aβ42 and increased tau and P-tau-181 levels (n = 50; correlating to an AD-like pathology). These CSF samples were analyzed using the AbsoluteIDQ® p180 Kit (BIOCRATES Life Sciences), which included 40 acylcarnitines, 21 amino acids, 19 biogenic amines, 15 sphingolipids, and 90 glycerophospholipids. Our data show that two sphingomyelins (SM (d18:1/18:0) and SM (d18:1/18:1)), 5 glycerophospholipids (PC aa C32:0, PC aa C34:1, PC aa C36:1, PC aa C38:4 and PC aa C38:6), and 1 acylcarnitine (C3-DC-M/C5-OH) were significantly altered in the CSF with pathological "AD-like pathology". Sphingomyelin SM (d18:1/18:0) proved to be a specific (76%) and sensitive (66%) biomarker with a defined cut-off of 546 nM. Correct diagnoses for 21 out of 32 unknown samples could be achieved using this SM (d18:1/18:0) cut-off value. In conclusion, the sphingolipid SM (d18:1/18:0) is significantly increased in CSF of patients displaying pathological levels of Aβ42, tau, and P-tau-181.

Assessing potential liver injury induced by Polygonum multiflorum using potential biomarkers via targeted sphingolipidomics

Pharm Biol 2022 Dec;60(1):1578-1590.PMID:35949191DOI:10.1080/13880209.2022.2099908.

Context: Polygonum multiflorum Thunb. (Polygonaceae) (PM) can cause potential liver injury which is typical in traditional Chinese medicines (TCMs)-induced hepatotoxicity. The mechanism involved are unclear and there are no sensitive evaluation indicators. Objective: To assess PM-induced liver injury, identify sensitive assessment indicators, and screen for new biomarkers using sphingolipidomics. Materials and methods: Male Sprague-Dawley (SD) rats were randomly divided into four groups (control, model with low-, middle- and high-dose groups, n = 6 each). Rats in the three model groups were given different doses of PM (i.g., low/middle/high dose, 2.7/8.1/16.2 g/kg) for four months. Alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels in the plasma and liver were quantitatively analyzed. Fixed liver tissue sections were stained with haematoxylin and eosin and examined under a light microscope. The targeted sphingolipidomic analysis of plasma was performed using high-performance liquid chromatography tandem mass spectrometry. Results: The maximal tolerable dose (MTD) of PM administered intragastrically to mice was 51 g/kg. Sphingolipid profiling of normal and PM-induced liver injury SD rats revealed three potential biomarkers: ceramide (Cer) (d18:1/24:1), dihydroceramide (d18:1/18:0)-1-phosphate (dhCer (d18:1/18:0)-1P) and Cer (d18:1/26:1), at 867.3-1349, 383.4-1527, and 540.5-658.7 ng/mL, respectively. A criterion for the ratio of Cer (d18:1/24:1) and Cer (d18:1/26:1) was suggested and verified, with a normal range of 1.343-2.368 (with 95% confidence interval) in plasma. Conclusions: Three potential biomarkers and one criterion for potential liver injury caused by PM that may be more sensitive than ALT and AST were found.