Katrin Strassburg, 1,2 Billy Joe Molloy, 5 Claude Mallet, 3 André Duesterloh, 4 Igor Bendik, 4 Thomas Hankemeier, 1,2 James Langridge, 5 Rob J. Vreeke
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1 Katrin Strassburg, 1,2 Billy Joe Molloy, 5 Claude Mallet, 3 André Duesterloh, 4 Igor Bendik, 4 Thomas Hankemeier, 1,2 James Langridge, 5 Rob J. Vreeken, 1,2 Giuseppe Astarita 3 1 Analytical Biosciences, LACDR, Leiden University, Leiden, The Netherlands; 2 Netherlands Metabolomics Centre, Leiden University, Leiden, The Netherlands; 3 Waters Corporation, Milford, MA, USA; 4 DSM Nutritional Products Europe Ltd., Switzerland; 5 Waters Corporation, Wilmslow, UK Oasis MAX SPE UPLC -ESI-MRM Xevo TQ-S 107 UPLC Xevo TQ -S Oasis MAX SPE TargetLynx A 1B 3 COX P450 CYP 1A 1B GC-MS UPLC-MS/MS MRM Xevo TQ-S 1
2 LC-MS 1-5 Strassburg Cayman # MRM V ev d4-6-keto PGF1α > d4-tbx > d4-pgf2α > d4-pge > d4-pgd > d5-lte > d4-ltb > d4-12,13-dihome > d4-9,10-dihome > d11-14,15-dihetre > d4-15-deoxy-δ12,14-pgj > d6-20-hete > d4-9-hode > d8-12-hete > d8-5-hete > UPLC-ESI-MS 2
3 UPLC ACQUITY UPLC Sigma-Aldrich Cayman Chemicals Ann Arbor, MI Biomol Plymouth Meeting, PA Larodan Malmo, Waters Oasis MAX 3 cc Vac 60 mg 30 µm p/n A B ACQUITY UPLC BEH C µm mm 0.1% / v/v 0.6 ml/min mm 1. 10% 200 µl µl 3. BHT 10 mg/ml 5 µl ng/ml 5 µl 5. 25% 3 ml MAX 1. 3 ml Oasis MAX SPE 2. 3 ml 25% Oasis MAX SPE 3. Oasis MAX SPE µl : A% B% MS UPLC ESI PEEK 1/16 in. 1.6 mm O.D. X in mm I.D. X 5 ft 1.5 m 400 mm MS Xevo TQ-S ESI MRM 2.5 kv 4. 3 ml 25% Oasis MAX SPE V 35 V 5. 3 ml Oasis MAX SPE % 1.3 ml 7. HPLC TruView Max L/ h 150 L/ h / µl 10. UPLC-MS/MS 3 µl 10% 200 µl ev 15 ev TargetLynx 3
4 1A 9,12,13-TriHOME 9,10,13-TriHOME 9-OxoODE 13-OxoODE 9-HODE 13-HODE 9-HpODE 13-HpODE Linoleic acid (LA) CYP450 12(13)-EpOME 9(10)-EpOME 12,13-DiHOME 9,10-DiHOME 9,12,13-TriHOME PGI 1 Dihomo- -linolenic acid (DGLA) COX 15-HETrE PGH 2 TXB 1 PGE 1 PGF 1 PGD 1 6-keto-PGE 1 COX Arachidonic acid (AA) CYP450 HETEs 6-keto-PGF 1 TXB 2 PGG 2 5-HETE HxB 3 PGI 2 PGH 2 TXA 2 5-HpETE 15-HpETE 12-HpETE 1B PGE 2 PGD 2 5-oxo-ETE PGF 2 LTC 4 PGA 2 PGJ 2 15-keto-PGF 2 PGC 2 PGB 2 LTD 4 12-PGJ 2 LTE 4 15-deoxy- 12-PGJ 2 LXB 4 HxA 3 12-oxo-ETE 12-HETE LTA 4 15(S)-HETE LXA 4 LTB 4 15-oxo-ETE 5(6)-EpETrE 8(9)-EpETrE 11(12)-EpETrE 14(15)-EpETrE 5,6-DiHETrE 8,9-DiHETrE 11,12-DiHETrE 14,15-DiHETrE Neuroprotectin D1 1. A. COX CYP-450 C18 : 2 LA - - C20:3 DHGLA C20:4 AA HOTrE -Linolenic acid (ALA) 13-HOTrE D-Resolvins 17(S)-HDHA 16(17)-EpDPE 17(S)-HpDHA Docosahexaenoic acid (DHA) 19,20-DiHDPA 19(20)-EpDPE CYP450 B. COX CYP C18 :3 ALA C20:5 EPA C22:6 DHA -3 COX TXB 3 PGG 3 PGI 3 TXA 3 PGH 3 PGE 3 PGD 3 PGF 3 5-HEPE LTC 3 LTD 3 LTE 3 5-HpEPE LTA 5 LTB 5 Eicosapentaenoic acid (EPA) 15-HpEPE 15(S)-HEPE 12-HpEPE 12-HEPE CYP450 5(6)-EpETE 8(9)-EpETE 11(12)-EpETE 14(15)-EpETE 17(18)-EpETE 5,6-DiHETE 8,9-DiHETE 11,12-DiHETE 14,15-DiHETE 17,18-DiHETE : DiHETE EpOME - HETrE HETE - HHTrE HODE HEPE - KETE - KODE PG TX 4
5 M1 M2 I.S. 1 Tetranor-PGFM (d4) PGF2α AA Prostanoid COX 2 Tetranor-PGEM (d4) PGE2 AA Prostanoid COX 3 20-hydroxy PGE (d4) PGE2 AA Prostanoid COX 4 Δ17-6-keto PGF1α (d4) 6-keto PGF1α AA Prostanoid COX 5 6-keto PGF1α (d4) 6-keto PGF1α AA Prostanoid COX 6 2,3-dinor-11b PGF2α (d4) PGF2α AA Prostanoid COX 7 (d4) 6-keto PGF1α ISTD 8 20-carboxy LTB (d4) LTB4 AA Leukotriene 9 6-keto PGE (d4) PGE2 AA Prostanoid COX hydroxy LTB (d4) LTB4 AA Leukotriene 11 TXB (d4) TXB2 EPA Thromboxane COX 12 PGF3α (d4) PGF2α EPA Prostanoid COX 13 TXB (d4) TXB2 DGLA Thromboxane COX 14 PGE (d4) PGE2 EPA Prostanoid COX 15 (d4) TXB ISTD 16 8-iso PGF2α (d4) PGF2α AA Isoprostane non enzymatic 17 TXB (d4) TXB2 AA Thromboxane COX 18 PGD (d4) PGD2 EPA Prostanoid COX 19 11β-PGF2α (d4) PGF2α AA Prostanoid COX 20 (+/-) 5-iPF2α-VI (d4) PGF2α AA Isoprostane non enzymatic 21 9,12,13-TriHOME (d4) 9(S)-HODE LA Triol 22 9,10,13-TriHOME (d4) 9(S)-HODE LA Triol 23 (d4) PGF2α ISTD 24 PGF2α (d4) PGF2α AA Prostanoid COX 25 PGF1α (d4) PGF2α DGLA Prostanoid COX 26 (d4) PGE ISTD 27 PGE (d4) PGE2 AA Prostanoid COX 28 11β-PGE (d4) PGE2 AA Prostanoid COX 29 PGK (d4) PGE2 AA Prostanoid COX keto PGF2α (d4) PGF2α AA Prostanoid COX 31 5(S),14(R)-Lipoxin B (d4) LTB4 AA Lipoxin 32 PGE (d4) PGE2 DGLA Prostanoid COX 33 (d4) PGD ISTD 34 PGD (d4) PGD2 AA Prostanoid COX 35 PGD (d4) PGD2 DGLA Prostanoid COX 36 11β-13,14-dihydro-15-keto (d4) PGF2α AA Prostanoid COX PGF2α keto PGF1α (d4) 6-keto PGF1α DGLA Prostanoid COX 38 13,14-dihydro PGF2α (d4) PGF2α AA Prostanoid COX 39 13,14-dihydro-15-keto PGE (d4) PGE2 AA Prostanoid COX 40 13,14-dihydro-15-keto PGF2α (d4) PGF2α AA Prostanoid COX 41 5(S),6(R)-Lipoxin A (d4) LTB4 AA Lipoxin 42 5(S),6(S)-Lipoxin A (d4) LTB4 AA Lipoxin 43 13,14-dihydro-15-keto PGF1α (d4) PGF2α AA Prostanoid COX 44 13,14-dihydro-15-keto PGD (d4) PGD2 AA Prostanoid COX 5
6 M1 M2 I.S. 45 1α,1b-dihomo PGF2α (d4) PGF2α ADA Prostanoid COX 46 14,15-LTE (d3) LTE4 AA Leukotriene 47 LTD (d3) LTE4 AA Leukotriene 48 Resolvin D (d11) 14,15-DiHETrE DHA rrsolving 49 Resolvin E (d11) 14,15-DiHETrE EPA Resolving 50 13,14-dihydro-15-keto PGD (d4) PGD2 AA Prostanoid COX 51 PGA (d4) PGE2 AA Prostanoid COX 52 Δ12-PGJ (d4) AA Prostanoid COX 15-deoxy-Δ12,14-PGJ2 53 PGJ (d4) PGD2 AA Prostanoid COX 54 LTB (d4) LTB4 EPA Leukotriene trans LTD (d3) LTE4 AA Leukotriene 56 (d3) LTE ISTD 57 LTE (d3) LTE4 AA Leukotriene 58 8(S),15(S)-DiHETE (d4) LTB4 AA Diol CYP ,13-DiHODE (d4) 9,10-DiHOME ALA Diol CYP bicyclo-pge (d4) PGE2 AA Prostanoid CYP trans LTE (d3) LTE4 AA Leukotriene 62 10(S),17(S)-DiHDoHE (d8) 12(S)-HETE DHA Protectin 63 Neuroprotectin D (d8) 12(S)-HETE DHA Protectin 64 17,18-DiHET E (d11) 14,15-DiHETrE EPA Diol CYP (S),15(S)-DiHETE (d4) LTB4 AA Diol CYP trans-LTB (d4) LTB4 AA Leukotriene 67 14,15-DiHETE (d11) 14,15-DiHETrE EPA Diol CYP (d4) LTB ISTD deoxy-Δ12,14-PGD (d4) AA Prostanoid COX 15-deoxy-Δ12,14-PGJ2 70 Hepoxilin A (d8) 12(S)-HETE AA Hepoxilin 71 LTB (d4) LTB4 AA Leukotriene 72 (d4)(±)12,13-dihome ISTD 73 12,13-DiHOME (d4) 12,13-DiHOME LA Diol CYP (d4)-(±)9,10-dihome ISTD 75 9,10-DiHOME (d4) 9,10-DiHOME LA Diol CYP (d11) 14,15-DiHETrE ISTD 77 19,20-DiHDPA (d11) 14,15-DiHETrE DHA Diol CYP ,15-DiHETrE (d11) 14,15-DiHETrE AA Diol CYP S-HHTrE (d8) 12(S)-HETE AA Alcohol COX 80 11,12-DiHETrE (d11) 14,15-DiHETrE AA Diol CYP ,6-DiHETrE (d11) 14,15-DiHETrE AA Diol CYP HOTrE (d4) 9(S)-HODE ALA Alcohol 83 17(18)-EpETE (d11) 14,15-DiHETrE EPA Epoxide CYP (d4) 15-deoxy-Δ12,14-PGJ ISTD 85 (d6) 20-HETE ISTD HETE d6-20-hete AA Alcohol CYP (S)-HEPE (d8) 5(S)-HETE EPA Alcohol 88 12(S)-HpETE (d8) 12(S)-HETE AA Hydroxyperoxide 6
7 M1 M2 I.S. 89 8,9-DiHETrE (d11) 14,15-DiHETrE AA Diol CYP (S),6(S)-DiHETE (d4) LTB4 AA Diol CYP (S)-HEPE (d8) 12(S)-HETE EPA Alcohol HODE (d4) 9(S)-HODE LA Alcohol 93 5(S)-HEPE (d8) 5(S)-HETE EPA Alcohol 94 (d4) 9(S)-HODE ISTD 95 9-HODE (d4) 9(S)-HODE LA Alcohol HETE (d8) 5(S)-HETE AA Alcohol 97 16(17)-EpDPE (d11) 14,15-DiHETrE DHA Epoxide CYP HpODE (d4) 9(S)-HODE LA Hydroxyperoxide KODE (d4) 9(S)-HODE LA Ketone HDoHE (d8) 5(S)-HETE DHA Alcohol HpODE (d4) 9(S)-HODE LA Hydroxyperoxide HpETE (d8) 5(S)-HETE AA Hydroxyperoxide KETE (d8) 5(S)-HETE AA Ketone HET E (d8) 12(S)-HETE AA Alcohol COX (15)-EpETE (d11) 14,15-DiHETrE EPA Epoxide CYP KODE (d4) 9(S)-HODE LA Ketone 107 (d8) 12(S)-HETE ISTD HETE (d8) 12(S)-HETE AA Alcohol HETE (d8) 5(S)-HETE AA Alcohol (S)-HETrE (d8) 5(S)-HETE DGLA Alcohol HETE (d8) 12(S)-HETE AA Alcohol non-enzymatic 112 (d8) 5(S)-HETE ISTD HETE (d8) 5(S)-HETE AA Alcohol (20)-EpDPE (d11) 14,15-DiHETrE DHA Epoxide CYP (13)-EpOME (d4) 12,13-DiHOME LA Epoxide CYP (15)-EpETrE (d11) 14,15-DiHETrE AA Epoxide CYP (S)-HpETE (d8) 5(S)-HETE AA Hydroxyperoxide 118 9(10)-EpOME (d4) 9,10-DiHOME LA Epoxide CYP KETE (d8) 12(S)-HETE AA Ketone KETE (d8) 5(S)-HETE AA Ketone (12)-EpETrE (d11) 14,15-DiHETrE AA Epoxide CYP (9)-EpETrE (d11) 14,15-DiHETrE AA Epoxide CYP (6)-EpETrE (d11) 14,15-DiHETrE AA Epoxide CYP MRM M1 ; M2 7
8 UPLC-MS SPE / SPE UPLC-MS/MS 2. UPLC 10 PGE2 PGD2 3 Xevo TQ-S ESI MRM 2 MRM R UPLC-MS/MS
9 Thromboxanes Triols Diols Hydroperoxides Tetranor-PGs PGs Leukotrienes Epoxides 6-keto-PGF1 TXB 2 PGD 2 LTE 4 12,142-PGJ 2 LTB 4 5(S)-HETE 20-HETE 12(S)-HEPE 12,13-DiHOME 9,10-DiHOME 9(S)-HODE 14,15-DiHETrE PGE 2 Retention time (min) 3. UPLC-MS/MS 14,15-DiHETrE (AA metabolite) 19,20-DiHDPE (DHA metabolite) 17,18-DiHETE (EPA metabolite) 12,13-DiHOME (LA metabolite) PGF2 (AA metabolite) PGF1 (DGLA metabolite) 4. 9
10 5. TargetLynx MRM 10
11 100 MRM Pro- SPE-UPLC-MRM 1. Lundstrom SL, Saluja R, Adner M, Haeggstrom JZ, Nilsson GP, Wheelock CE. Lipid mediator metabolic profiling demonstrates differences in eicosanoid patterns in Two phenotypically distinct mast cell populations. J Lipid Res Oct 3. [Epub ahead of print]. 2. Strassburg K, Huijbrechts AM, Kortekaas KA, Lindeman JH, Pedersen TL, Dane A,Berger R, Brenkman A, Hankemeier T, van Duynhoven J, Kalkhoven E, Newman JW, Vreeken RJ. Quantitative profiling of oxylipins through comprehensive LC-MS/MS analysis: application in cardiac surgery. Anal Bioanal Chem Sep;404(5): Sterz K, Scherer G, Ecker J. A simple and robust UPLC-SRM/MS method to quantify urinary eicosanoids. J Lipid Res May;53(5): Nicolaou A, Masoodi M, Mir A. Lipidomic analysis of prostanoids by liquid chromatography-electrospray tandem mass spectrometry. Methods Mol Biol. 2009;579: Astarita G, Kendall AC, Dennis EA, Nicolaou A. Targeted lipidomics strategies for oxygenated metabolites of polyunsaturated fatty acids. Biochim Biophys Acta Dec 5. pii: S (14) TEL FAX F TEL FAX Waters UPLC ACQUITY UPLC Xevo Oasis The Science of What s Possible Waters Corporation TruView TargetLynx Waters Corporation 2015 Waters Corporation. Produced in Japan JA PDF
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