Sphingosine (d17:1) |
| Catalog No.: GC44932 |
Sphingosine is an amino alcohol most commonly characterized by an 18-carbon unsaturated hydrocarbon chain sphingosine (d18:1).
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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Purity: >98.00%
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- Datasheet
Sphingosine is an amino alcohol most commonly characterized by an 18-carbon unsaturated hydrocarbon chain sphingosine (d18:1) . However, the hydrocarbon chain length of sphingosine, and the related dihydrosphingosine, can vary from 12-26 carbons in mammalian tissues. Sphingosine (d17:1) is a naturally-occurring but uncommon form of sphingosine, accounting for approximately 13% of the sphingosine in human skin. It can be phosphorylated by sphingosine kinases to produce C-17 sphingosine-1-phosphate. More commonly, sphingosine C-17 is used as an internal standard in the analysis of sphingoid compounds by chromatographic or spectrometric methods.
| Cas No. | 6918-48-5 | SDF | |
| Canonical SMILES | OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCC | ||
| Formula | C17H35NO2 | M.Wt | 285.5 |
| Solubility | DMF: 10 mg/ml,DMSO: 2 mg/ml,Ethanol: Miscible | Storage | Store at -20°C |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
| Shipping Condition | Evaluation sample solution : ship with blue ice All other available size: ship with RT , or blue ice upon request |
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Immunomodulatory sphingosine-1-phosphates as plasma biomarkers of Alzheimer's disease and vascular cognitive impairment
Alzheimers Res Ther 2020 Sep 30;12(1):122.PMID:32998767DOI:10.1186/s13195-020-00694-3.
Background: There has been ongoing research impetus to uncover novel blood-based diagnostic and prognostic biomarkers for Alzheimer's disease (AD), vascular dementia (VaD), and related cerebrovascular disease (CEVD)-associated conditions within the spectrum of vascular cognitive impairment (VCI). Sphingosine-1-phosphates (S1Ps) are signaling lipids which act on the S1PR family of cognate G-protein-coupled receptors and have been shown to modulate neuroinflammation, a process known to be involved in both neurodegenerative and cerebrovascular diseases. However, the status of peripheral S1P in AD and VCI is at present unclear. Methods: We obtained baseline bloods from individuals recruited into an ongoing longitudinal cohort study who had normal cognition (N = 80); cognitive impairment, no dementia (N = 160); AD (N = 113); or VaD (N = 31), along with neuroimaging assessments of cerebrovascular diseases. Plasma samples were processed for the measurements of major S1P species: d16:1, d17:1, d18:0, and d18:1, along with pro-inflammatory cytokines interleukin (IL)-6, IL-8, and tumor necrosis factor (TNF). Furthermore, in vitro effects of S1Ps on cytokine expression were also studied in an astrocytoma cell line and in rodent primary astrocytes. Results: Of the S1Ps species measured, only d16:1 S1P was significantly reduced in the plasma of VaD, but not AD, patients, while the d18:1 to d16:1 ratios were increased in all cognitive subgroups (CIND, AD, and VaD). Furthermore, d18:1 to d16:1 ratios correlated with levels of IL-6, IL-8, and TNF. In both primary astrocytes and an astroglial cell line, treatment with d16:1 or d18:1 S1P resulted in the upregulation of mRNA transcripts of pro-inflammatory cytokines, with d18:1 showing a stronger effect than d16:1. Interestingly, co-treatment assays showed that the addition of d16:1 reduced the extent of d18:1-mediated gene expression, indicating that d16:1 may function to "fine-tune" the pro-inflammatory effects of d18:1. Conclusion: Taken together, our data suggest that plasma d16:1 S1P may be useful as a diagnostic marker for VCI, while the d18:1 to d16:1 S1P ratio is an index of dysregulated S1P-mediated immunomodulation leading to chronic inflammation-associated neurodegeneration and cerebrovascular damage.
Quantifying Sphingomyelin in Dairy through Infusion-Based Shotgun Mass Spectrometry with Lithium-Ion-Induced Fragmentation
J Agric Food Chem 2022 Oct 26;70(42):13808-13817.PMID:36239443DOI:10.1021/acs.jafc.2c04587.
Quantifying sphingomyelin (SM) species by infusion-based mass spectrometry (MS) is complicated by the presence of isobaric phosphatidylcholine (PC) species, which generate a common m/z 184 product ion in the presence of ammonium ions as a result of the phosphocholine headgroup. Lithium ion adducts of SM undergo a selective dehydration [Li + H2O + (CH3)3NC2H4PO4] with a corresponding neutral loss of -207 Da. This neutral loss was employed to create a SM-selective method for identifying target species, which were quantitated using multiple reaction monitoring (MRM). SM-selective fragments in MS3 were used to characterize the Sphingosine base and acyl chain. These methods were used to identify 50 individual SM species in bovine milk ranging from SM 28:1 to SM 44:2, with d16:1, d17:1, d18:1, d19:1, and d20:1 bases, and acyl fatty acids ranging from 10 to 25 carbons and 0-1 desaturations. Spiked SM standards into milk had a recovery of 99.7%, and endogenous milk SM had <10% coefficient of variation for both intra- and interday variability, with limits of detection of 1.4-5.55 nM and limits of quantitation of 11.8-178.1 nM. This MS-MRM method was employed to accurately and precisely quantify SM species in dairy products, including bovine-derived whole milk, half and half, whipping cream, and goat milk.
Free sphingosines in porcine epidermis
Biochim Biophys Acta 1989 Apr 3;1002(2):213-7.PMID:2930769DOI:10.1016/0005-2760(89)90289-0.
Sphingosines and phytosphingosines serve as intermediates in the synthesis of ceramides and glucosylceramides, which are prominent components of mammalian epidermis. In the present study, we have investigated the possibility that free sphingoid bases also may be present in epidermal tissue. Samples of pig epidermis were trypsinized to separate the stratum corneum from the unkeratinized portion of the epidermis. After drying, the lipids were extracted and analyzed by thin-layer chromatography using ninhydrin to detect free amino groups. Both the stratum corneum and the unkeratinized epidermal material contained a ninhydrin-positive material with the same mobility as the Sphingosine standard. Quantitation of the chromatograms by photodensitometry indicated that free Sphingosine bases account for 0.44% by weight of the total stratum corneum lipid and 0.09% of the lipid in the viable portion of the epidermis. To further identify this material, it was treated with 1-fluoro-2,4-dinitrobenzene, which resulted in the production of an intensely yellow N-2,4-dinitrophenyl derivative with the same mobility as N-2,4-dinitrophenylsphingosine on thin-layer chromatography. Oxidation of the isolated dinitrophenyl derivative with lead tetraacetate produced a mixture of aldehydes which were analyzed by gas-liquid chromatography. This analysis indicates that the free sphingoid bases from the stratum corneum consist of a mixture of mainly 16- through 20-carbon sphingenines and sphinganines, the most abundant components being d17:0, d17:1, d18:1 and d20:1. The production of these free Sphingosine bases may be significant in regulating epidermal differentiation.
The Long-Chain Sphingoid Base of Ceramides Determines Their Propensity for Lateral Segregation
Biophys J 2017 Mar 14;112(5):976-983.PMID:28297656DOI:10.1016/j.bpj.2017.01.016.
We examined how the length of the long-chain base or the N-linked acyl chain of ceramides affected their lateral segregation in 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) bilayers. Lateral segregation and ceramide-rich phase formation was ascertained by a lifetime analysis of trans-parinaric acid (tPA) fluorescence. The longer the length of the long-chain base (d16:1, d17:1, d18:1, d19:1, and d20:1 in N-palmitoyl ceramide), the less ceramide was needed for the onset of lateral segregation and ceramide-rich phase formation. A similar but much weaker trend was observed when Sphingosine (d18:1)-based ceramide had N-linked acyl chains of increasing length (14:0 and 16:0-20:0 in one-carbon increments). The apparent lateral packing of the ceramide-rich phase, as determined from the longest-lifetime component of tPA fluorescence, also correlated strongly with the long-chain base length, but not as strongly with the N-acyl chain length. Finally, we compared two ceramide analogs with equal carbon numbers (d16:1/17:0 or d20:1/13:0) and observed that the analog with a longer sphingoid base segregated at lower bilayer concentrations to a ceramide-rich phase compared with the shorter sphingoid base analog. The gel phase formed by d20:1/13:0 ceramide also was more thermostable than the gel phase formed by d16:1/17:0 ceramide. 2H NMR data for 10 mol % stearoyl ceramide in POPC also showed that the long-chain base was more ordered than the acyl chain at comparable chain positions and temperatures. We conclude that the long-chain base length of ceramide is more important than the acyl chain length in determining the lateral segregation of the ceramide-rich gel phase and intermolecular interactions therein.
Serum lipidome analysis of healthy beagle dogs receiving different diets
Metabolomics 2019 Dec 3;16(1):1.PMID:31797205DOI:10.1007/s11306-019-1621-3.
Introduction: Food and dietary ingredients have significant effects on metabolism and health. Objective: To evaluate whether and how different diets affected the serum lipidomic profile of dogs. Methods: Sixteen healthy beagles were fed a commercial dry diet for 3 months (control diet). After an overnight fasting period, a blood sample was taken for serum lipidomic profile analysis, and each dog was then randomly assigned to one of two groups. Group 1 was fed a commercial diet (Diet 1) and group 2 was fed a self-made, balanced diet supplemented with linseed oil and salmon oil (Diet 2) for 3 months. After an overnight fasting period, a blood sample was taken from each dog. Serum cholesterol and triacylglycerol analyses were performed and the serum lipidomic profiles were analyzed using targeted liquid chromatography-mass spectrometry. Results: Dogs fed the supplemented self-made diet (Diet 2) had significantly higher omega-3 fatty acid-containing lipids species and significantly lower saturated and mono- and di-unsaturated lipid species. Concentrations of Sphingosine 1-phosphate species S1P d16:1 and S1P d17:1 were significantly increased after feeding Diet 2. Conclusion: This study found that different diets had significant effects on the dog's serum lipidomic profile. Therefore, in studies that include lipidomic analyses, diet should be included as a confounding factor.
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