Triethylamine, 4-(dimethylamino)phenyl isocyanate, formic acid and butylated hydroxytoluene (BHT) were obtained from Sigma-Aldrich (Saint-Quentin Fallavier, France). Hexane and dichloromethane were obtained from CarloErbaReactifs SDS (Val-de-Reuil, France). Acetonitrile, methanol, isopropanol were of LC-MS grade (J.T. Baker, Phillipsburg, NJ, USA). 24(R/S)-hydroxycholesterol d6 [26,26,26,27,27,27-hexadeuterocholest-5-ene-3ß,24-diol], cholesterol d7 [cholest-5-en-3ß-ol(d7)], 1,2-diheptadecanoyl-sn-glycero-3-phosphate, PA(17:0/17:0), 1,2-diheptadecanoyl-sn-glycero-3-phospho-L-serine, PS (17:0/17:0), 1,2-diheptadecanoyl-sn-glycero-3-phosphoethanolamine, PE(17:0/17:0), 1,2-diheptadecanoyl-sn-glycero-3-phosphocholine, PC(17:0/17:0), 1,2-diheptadecanoyl-sn-glycero-3-phospho-(1′-rac-glycerol), PG(17:0/17:0), 1,2-diheptadecanoyl-sn-glycerol, DG (17:0/17:0/0:0) and N-heptadecanoyl-D-erythro-sphingosine, Cer(d18:1(4E)/17:0) were obtained from Avanti Polar Lipids, Inc. (Alabaster, AL, USA).
N heptadecanoyl d erythro sphingosine
Manufactured by Avanti Polar Lipids
Sourced in United States
N-heptadecanoyl-d-erythro-sphingosine is a synthetic sphingolipid compound. It functions as a chemical standard and reference material for analytical and research applications.
Automatically generated - may contain errors
Lab products found in correlation
1 2 dimyristoyl sn glycero 3 phosphocholine, by Avanti Polar Lipids (3 mentions)
N heptadecanoyl d erythro sphingosylphosphorylcholine, by Avanti Polar Lipids (3 mentions)
1 2 dimyristoyl sn glycero 3 phosphoethanolamine, by Avanti Polar Lipids (2 mentions)
1 nonadecanoyl 2 hydroxy sn glycero 3 phosphocholine, by Avanti Polar Lipids (2 mentions)
1 2 dipalmitoyl sn glycero 3 phosphatidylinositol, by Avanti Polar Lipids (2 mentions)
Sodium taurocholate, by Fujifilm (2 mentions)
10 cm cell culture dishes, by Corning (2 mentions)
Triolein, by Fujifilm (2 mentions)
D glucosyl 1 1 n lauroyl d erythrosphingosine, by Avanti Polar Lipids (2 mentions)
2 amino 4 trans heptadecene 1 3 diol, by Avanti Polar Lipids (2 mentions)
Fetal bovine serum (fbs), by Thermo Fisher Scientific (2 mentions)
Butylated hydroxytoluene, by Merck Group (1 mentions)
4 dimethylamino phenyl isocyanate, by Merck Group (1 mentions)
Acetonitrile, by Avantor (1 mentions)
Formic acid, by Merck Group (1 mentions)
Triethylamine, by Merck Group (1 mentions)
Dichloromethane, by Carlo Erba (1 mentions)
Hexane, by Carlo Erba (1 mentions)
6 hydroxyl 2 5 7 8 tetramethylchromane 2 carboxylic acid trolox, by Merck Group (1 mentions)
Milli q water synergy, by Merck Group (1 mentions)
9 protocols using n heptadecanoyl d erythro sphingosine
1
Lipid Standards for Mass Spectrometry
2
Phospholipid Standards Characterization
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Dichloromethane (CH2Cl2), methanol (MeOH), and acetonitrile (high-performance liquid chromatography—HPLC, grade) were purchased from Fisher Scientific Ltd. (Loughborough, UK). Milli-Q water (Synergy, Millipore Corporation, Billerica, MA, USA) was used. Phospholipid standards: 1,2-dimyristoyl-sn-glycero-3- phosphocholine (dMPC), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dMPE), 1,2-dimyristoyl-sn-glycero-3-phospho-(1′-rac-)glycerol (dMPG), 1,2-dipalmitoyl-sn-glycero-3-phosphatidylinositol (dPPI), 1–nonadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC), dimyristoyl phosphatidic acid (dMPA), and N-heptadecanoyl-D-erythro-sphingosine (Cer (d18:1/17:0)) were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL).
2,2-Diphenyl-1-picrylhydrazyl (DPPH) was purchased from Aldrich (Milwaukee, WI). 2,2’-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) was obtained from Fluka (Buchs, Switzerland). Ammonium acetate and 6-hydroxyl-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox) were purchased from Sigma-Aldrich (St Louis, MO, USA). All other reagents and chemicals used were of the highest grade of purity and were purchased from major commercial sources.
2,2-Diphenyl-1-picrylhydrazyl (DPPH) was purchased from Aldrich (Milwaukee, WI). 2,2’-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) was obtained from Fluka (Buchs, Switzerland). Ammonium acetate and 6-hydroxyl-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox) were purchased from Sigma-Aldrich (St Louis, MO, USA). All other reagents and chemicals used were of the highest grade of purity and were purchased from major commercial sources.
3
HPLC-MS Lipid Standards Characterization
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HPLC-grade ammonium formate and LC-MS-grade formic acid were purchased from Fluka Chemie (Buchs, Switzerland). LC-MS-grade acetonitrile (ACN), methanol (MeOH), and ACS-grade chloroform were purchased from J.T. Baker or Mallinckrodt (Mallinckrodt Baker Inc. Phillipsburg, NJ, USA). 2,6-di-tert-butyl-4-methylphenol (butylated hydroxytoluene; BHT) was purchased from Sigma Chemical Co. (St. Louis, MO, USA). 2,3,5-triphenyl-tetrazolium chloride (TTC) was purchased from Alfa Aesar (Lancashire, U.K.). Water (18.2 MΩ/cm) was purified in house using a Synergy Ultrapure Water System (Millipore Co., Burlington, MA, USA). The following lipid standards were purchased from Avanti Polar Lipids Inc. (Alabaster, AL, USA): 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC 14:0), 1-myristoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine (LPE 14:0), 1,2-dimyristoyl-sn-glycero-3-phosphocholine (PC 14:0/14:0), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (PE 14:0/14:0), N-lauroyl-D-erythro-sphingosylphosphorylcholine (SM d18:1/12:0), and N-heptadecanoyl-D-erythro-sphingosine (ceramide d18:1/17:0).
4
Analytical Reagents and Lipid Standards for HPLC-based Lipidomics
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High-performance liquid chromatography (HPLC)-grade dichloromethane (CH2Cl2), absolute ethanol 96% (CH3CH2OH), and methanol (CH3OH) were obtained from Fisher Scientific Ltd. (Loughborough, UK). Milli-Q purified water (Synergy1, Millipore Corporation, Billerica, MA, USA) was used in all experiments. The 2,2-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS●+) was purchased from Fluka (Buchs, Switzerland) and the α,α-diphenyl-β-pic-rylhydrazyl radical (DPPH●) from Aldrich (Milwaukee, WI, USA). All the remaining reagents were obtained from primary commercial sources. The lipid internal standards used in the lipidome analyses were acquired from Avanti Polar Lipids, Inc. (Alabaster, AL, USA): 1,2-dimyristoyl-sn-glycero-3-phosphate (dMPA), 1,2-dimyristoyl-sn-glycero-3-phospho-(10-rac-glycerol) (dMPG), 1,2-dimyristoyl-sn-glycero-3-phosphocholine (dMPC), 1,2-dipalmitoyl-sn-glycero-3-phosphatidylinositol (dPPI), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dMPE), 1,2-dimyristoyl-sn-glycero-3-phosphatidylserine (dMPS), 1-nonadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC), N-heptadecanoyl-D-erythro-sphingosine (Cer), and 1′,3′-bis-[1-2-di-tetradecanoyl-sn-glycero-3-phospho]-sn-glycerol (CL), and N-heptadecanoyl-D-erythro-sphingosylphosphorylcholine (SM).
5
Comprehensive Lipid Extraction and Analysis
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All of the organic solvents used had HPLC purity and they were purchased from Fisher Scientific Ltd. (Loughborough, UK): chloroform (CHCl3), methanol (MeOH), n-hexane, acetonitrile, and diethyl ether. Other reagents were purchased from major commercial sources. Purified water (Synergy, Millipore Corporation, Billerica, MA, USA) was used whenever necessary. Phospholipid internal standards were obtained from Avanti Polar Lipids, Inc. (Alabaster, AL; USA): 1,2-dimyristoyl-sn-glycero-3-phosphocholine (dMPC); 1-nonadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine (LPC); N-palmitoyl-d -erythro-sphingosylphosphorylcholine (NPSM); 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (dMPE); 1,2-dimyristoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (dMPG); 1,2-dimyristoyl-sn-glycero-3-phospho-l -serine (dMPS); 1,2-dipalmitoyl-sn-glycero-3-phosphatidylinositol (dPPI); 1,2-dimyristoyl-sn-glycero-3-phosphate (dMPA); 1,1′,2,2′-tetramyristoyl cardiolipin; and, N-heptadecanoyl-d -erythro-sphingosine (C17 Cer(d35:1)).
6
Quantitative Sphingolipid Profiling
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CER an SM were extracted according to the method by Kirklund (ref) in the presence of deuterium-labeled standards (N-heptadecanoyl-D-erythro-sphingosine (C17:0-Ceramide); Npalmitoyl(d31)-D-erythro-sphingosylphosphorylcholine (C16:0D31SM) from Avanti Polar Lipids, Alabama, USA). Briefly, total lipids were extracted from 2 mg of lyophilized BS or BM in chloroform:methanol (1:2 v/v) after addition of internal standards. Sphingolipids were isolated by a step of saponification, fractionated and desalted using reverse-phase Bond Elut C18 columns (Kyrklund, 1987) . The dry extracts were kept at -20°C until tandem mass spectrometry analysis.
Samples were homogenised in chloroform:methanol (1:2 v/v) and analysed by direct flow injection on an triple-quadrupole mass spectrometer (API 4500 QTRAP MS/MS; Sciex Applied Biosystems, Toronto, Canada) in the positive ionization mode using the multiple reaction monitoring (MRM) method. CER and SM species were measured separately, with two different methods with a flow rate of 200µl/min (analysis time of 3 minutes). The concentration of each molecular species was calculated from the ratio of its signal to that of the corresponding internal standard. Total CER concentration was the sum of the concentrations of the various species.
Samples were homogenised in chloroform:methanol (1:2 v/v) and analysed by direct flow injection on an triple-quadrupole mass spectrometer (API 4500 QTRAP MS/MS; Sciex Applied Biosystems, Toronto, Canada) in the positive ionization mode using the multiple reaction monitoring (MRM) method. CER and SM species were measured separately, with two different methods with a flow rate of 200µl/min (analysis time of 3 minutes). The concentration of each molecular species was calculated from the ratio of its signal to that of the corresponding internal standard. Total CER concentration was the sum of the concentrations of the various species.
7
Lipid Transport Assay in Caco-2 Cells
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N-heptadecanoyl-d-erythro-sphingosine (C17 ceramide; d18:1-C17:0), N-heptadecanoyl-d-erythrosphingosylphosphorylcholine (C17 sphingomyelin; d18:1-C17:0), d-glucosyl-1,1'-N-lauroyl-d-erythrosphingosine (C12 glucosylceramide; d18:1-C12:0), and 2-amino-4-trans-heptadecene-1,3-diol (d17:1) were obtained from Avanti Polar Lipids (Alabaster, Alabama, USA). Triolein and sodium taurocholate were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Caco-2 cells were obtained from RIKEN BioResource Center. FBS was purchased from Life Technologies, Inc. (Gaithersburg, Maryland, USA). DMEM, non-essential amino acids solution (NEAA), penicillin-streptomycin solution (P/S), trypsin-EDTA solution, and b-glucosidase from almonds were from Merck KGaA (Darmstadt, Germany). Falcon six-well cell culture insert plates (high pore density, pore size 0.4 mm) and 10 cm cell culture dishes were purchased from Corning (New York, USA).
8
Lipid Standards for Cell Culture Experiments
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N-heptadecanoyl-d -erythro-sphingosine [C17 ceramide; Cer 18:1(4E);2OH/17:0], N-heptadecanoyl-d -erythro-sphingosylphosphorylcholine [C17 SM; SM 18:1(4E);2OH/17:0], d -glucosyl-1,1′-N-lauroyl-d -erythro-sphingosine [C12 GlcCer; GlcCer 18:1(4E);2OH/12:0], and 2-amino-4-trans-heptadecene-1,3-diol [LCB 17:1(4E);2OH] were obtained from Avanti Polar Lipids (Alabaster, Alabama, USA). Triolein and sodium taurocholate were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Caco-2 cells (ECA86010202) were obtained from the RIKEN BioResource Center (Tsukuba, Ibaraki, Japan). Fetal bovine serum (FBS) was purchased from Life Technologies, Inc. (Gaithersburg, MD, USA). Dulbecco’s Modified Eagle Medium (DMEM), non-essential amino acid solution (NEAA), penicillin-streptomycin solution (P/S), trypsin- ethylenediaminetetraacetic acid solution, and β-glucosidase from almonds were obtained from Merck KGaA (Darmstadt, Germany). Six-well Falcon cell culture insert plates (high pore density, pore size 0.4 μm) and 10-cm cell culture dishes were purchased from Corning (New York, USA).
9
Quantitative Lipid Profiling by LC-MS/MS
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Methanol, formic acid and tert‐butyl methyl ether (MTBE) were purchased from Carlo Erba. Ammonium formate was purchased from Sigma‐Aldrich. d ‐Glucosyl‐β1‐1′‐N‐tetracosanoyl‐d‐erythro‐sphingosine (GL1; d18:1/24:0) from Matreya LLC. d‐Glucosyl‐β1‐1′‐d‐erythro‐sphingosine (Lyso‐GL1; d18:1), d‐erythro‐sphingosine (Sph; d18:1), d‐erythro‐sphingosine 1‐phosphate (S1P; d18:1), and the internal standards (IS) C17‐d‐erythro‐sphingosine (C17B; d17:1), C17‐d‐erythro‐sphingosine‐1‐phosphate (C17‐S1P; d17:1) and N‐heptadecanoyl‐d‐erythro‐sphingosine (C17Cer; d18:1/17:0) were obtained from Avanti Polar Lipids.
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