Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS

Analytical and Bioanalytical Chemistry

Volumn 407, Issue 6, 2015, Pages 1625-1639

  Sasaki, Ai ^a   Fukuda, Hayato ^a   Shiida, Narumi ^a   Tanaka, Nobuaki ^b   Furugen, Ayako ^a   Ogura, Jiro ^a   Shuto, Satoshi ^a   Mano, Nariyasu ^b,c   Yamaguchi, Hiroaki ^b,c  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY HOSPITAL   (Japan)

Author keywords

Eicosanoids; Polyunsaturated fatty acids; Specialized pro resolving mediators; UPLC MS MS; Urine

Indexed keywords

BIOMOLECULES; BODY FLUIDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; POLYUNSATURATED FATTY ACIDS; UNSATURATED FATTY ACIDS;

CORRELATION COEFFICIENT; EICOSANOIDS; OMEGA-3 POLYUNSATURATED FATTY ACIDS; QUANTITATIVE DETERMINATIONS; SPECIALIZED PRO-RESOLVING MEDIATORS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; UPLC/MS/MS; URINE;

FATTY ACIDS;

BIOLOGICAL MARKER; OMEGA 3 FATTY ACID; OMEGA 6 FATTY ACID;

HUMAN; LIQUID CHROMATOGRAPHY; PROCEDURES; REPRODUCIBILITY; STANDARD; TANDEM MASS SPECTROMETRY; URINE;

BIOLOGICAL MARKERS; CHROMATOGRAPHY, LIQUID; FATTY ACIDS, OMEGA-3; FATTY ACIDS, OMEGA-6; HUMANS; REFERENCE STANDARDS; REPRODUCIBILITY OF RESULTS; TANDEM MASS SPECTROMETRY;

EID: 84937035782     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-014-8412-5     Document Type: Article

References (42)

1. Buczynski MW, Dumlao DS, Dennis EA (2009) Thematic review series: proteomics. An integrated omics analysis of eicosanoid biology. J Lipid Res 50:1015-1038
2. Hishinuma T, Koseki Y, Murai Y, Yamazaki T, Suzuki K, Mizugaki M (1999) Urinary thromboxane A2/prostacyclin balance reflects the pathological state of a diabetic. Prostaglandins Other Lipid Mediat 58:263-271
3. Murphey LJ, Williams MK, Sanchez SC, Byrne LM, Csiki I, Oates JA, Johnson DH, Morrow JD (2004) Quantification of the major urinary metabolite of PGE2 by a liquid chromatographic/mass spectrometric assay: determination of cyclooxygenase-specific PGE2 synthesis in healthy humans and those with lung cancer. Anal Biochem 334:266-275
4. Cai Q, Gao YT, Chow WH, Shu XO, Yang G, Ji BT, Wen W, Rothman N, Li HL, Morrow JD, Zheng W (2006) Prospective study of urinary prostaglandin E2 metabolite and colorectal cancer risk. J Clin Oncol 24:5010-5016
5. Dong LM, Shu XO, Gao YT, Milne G, Ji BT, Yang G, Li HL, Rothman N, Zheng W, Chow WH, Abnet CC (2009) Urinary prostaglandin E2 metabolite and gastric cancer risk in the Shanghai women's health study. Cancer Epidemiol Biomarkers Prev 18:3075-3078
6. Ono E, Taniguchi M, Mita H, Fukutomi Y, Higashi N, Miyazaki E, Kumamoto T, Akiyama K (2009) Increased production of cysteinyl leukotrienes and prostaglandin D2 during human anaphylaxis. Clin Exp Allergy 39:72-80
7. Abd El-Motaleb GS, Abou Amer AA, Elawa GM, Abo Alsood Abd Elfattah M (2014) Study of urinary leukotriene E4 levels in children with acute asthma. Int J Gen Med 7:131-135
8. González-Núñez D, Claria J, Rivera F, Poch E (2001) Increased levels of 12(S)-HETE in patients with essential hypertension. Hypertension 37:334-338
9. Olson MT, Kickler TS, Lawson JA, McLean RC, Jani J, FitzGerald GA, Rade JJ (2012) Effect of assay specificity on the association of urine 11-dehydro thromboxane B2 determination with cardiovascular risk. J Thromb Haemost 10:2462-2469
10. Kim KM, Jung BH, Paeng KJ, Kim I, Chung BC (2004) Increased urinary F(2)-isoprostanes levels in the patients with Alzheimer's disease. Brain Res Bull 64:47-51
11. Ohnishi H, Saito Y (2013) Eicosapentaenoic acid (EPA) reduces cardiovascular events: relationship with the EPA/arachidonic acid ratio. J Atheroscler Thromb 20:861-877
12. Sublette ME, Galfalvy HC, Hibbeln JR, Keilp JG, Malone KM, Oquendo MA, Mann JJ (2014) Polyunsaturated fatty acid associations with dopaminergic indices in major depressive disorder. Int J Neuropsychopharmacol 17:383-391
13. Leitzmann MF, Stampfer MJ, Michaud DS, Augustsson K, Colditz GC, Willett WC, Giovannucci EL (2004) Dietary intake of n-3 and n-6 fatty acids and the risk of prostate cancer. Am J Clin Nutr 80:204-216
14. Bannenberg G, Serhan CN (2010) Specialized pro-resolving lipid mediators in the inflammatory response: an update. Biochim Biophys Acta 1801:1260-1273
15. Serhan CN (2007) Resolution phase of inflammation: novel endogenous anti-inflammatory and proresolving lipid mediators and pathways. Annu Rev Immunol 25:101-137
16. Serhan CN (2010) Novel lipid mediators and resolution mechanisms in acute inflammation: to resolve or not? Am J Pathol 177:1576-1591
17. Ridker PM (2009) Testing the inflammatory hypothesis of atherothrombosis: scientific rationale for the cardiovascular inflammation reduction trial (CIRT). J Thromb Haemost 1:332-339
18. Aggarwal BB, Shishodia S, Sandur SK, Pandey MK, Sethi G (2006) Inflammation and cancer: how hot is the link? Biochem Pharmacol 72:1605-1621
19. Janakiram NB, Mohammed A, Rao CV (2011) Role of lipoxins, resolvins, and other bioactive lipids in colon and pancreatic cancer. Cancer Metastasis Rev 30:507-523
20. Tsikas D, Zoerner AA (2014) Analysis of eicosanoids by LC-MS/MS and GC-MS/MS: a historical retrospect and a discussion. J Chromatogr B Analyt Technol Biomed Life Sci 964:79-88
21. Tsikas D (1998) Application of gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry to assess in vivo synthesis of prostaglandins, thromboxane, leukotrienes, isoprostanes and related compounds in humans. J Chromatogr B Biomed Sci Appl 717:201-245
22. Schweer H, Kammer J, Kühl PG, Seyberth HW (1986) Determination of peripheral plasma prostanoid concentration: an unreliable index of 'in vivo' prostanoid activity. Eur J Clin Pharmacol 31:303-305
23. Roberts LJ, Morrow JD (2000) Measurement of F(2)-isoprostanes as an index of oxidative stress in vivo. Free Radic Biol Med 28:505-513
24. Morrow JD, Hill KE, Burk RF, Nammour TM, Badr KF, Roberts LJ (1990) A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc Natl Acad Sci U S A 87:9383-9387
25. Yan Z, Mas E, Mori TA, Croft KD, Barden AE (2010) A significant proportion of F2-isoprostanes in human urine are excreted as glucuronide conjugates. Anal Biochem 403:126-128
26. Taylor AW, Bruno RS, Traber MG (2008) Women and smokers have elevated urinary F(2)-isoprostane metabolites: a novel extraction and LC-MS methodology. Lipids 43:925-936
27. Neale JR, Dean BJ (2008) Liquid chromatography-tandem mass spectrometric quantification of the dehydration product of tetranor PGE-M, the major urinary metabolite of prostaglandin E(2) in human urine. J Chromatogr B Analyt Technol Biomed Life Sci 871:72-77
28. Sterz K, Scherer G, Ecker J (2012) A simple and robust UPLC-SRM/MS method to quantify urinary eicosanoids. J Lipid Res 53:1026-1036
29. Gosetti F, Mazzucco E, Zampieri D, Gennaro MC (2010) Signal suppression/enhancement in high-performance liquid chromatography tandem mass spectrometry. J Chromatogr A 1217:3929-3937
30. Song WL, Lawson JA, Wang M, Zou H, FitzGerald GA (2007) Noninvasive assessment of the role of cyclooxygenases in cardiovascular health: a detailed HPLC/MS/MS method. Methods Enzymol 433:51-72
31. Yan W, Byrd GD, Ogden MW (2007) Quantitation of isoprostane isomers in human urine from smokers and nonsmokers by LC-MS/MS. J Lipid Res 48:1607-1617
32. Pelikan Z (2011) Delayed asthmatic response to bronchial challenge with allergen-mediators, eicosanoids, eosinophil and neutrophil constituents in the blood and urine. Respiration 82:225-236
33. Blatnik M, Steenwyk RC (2010) Quantification of urinary PGEm, 6-keto PGF(1alpha) and 2,3-dinor-6-keto PGF(1alpha) by UFLC-MS/MS before and after exercise. Prostaglandins Other Lipid Mediat 93:8-13
34. Yamaguchi H, Higashi N, Mita H, Ono E, Komase Y, Nakagawa T, Miyazawa T, Akiyama K, Taniguchi M (2011) Urinary concentrations of 15-epimer of lipoxin A(4) are lower in patients with aspirin-intolerant compared with aspirin-tolerant asthma. Clin Exp Allergy 41:1711-1718
35. Lorenz R, Helmer P, Uedelhoven W, Zimmer B, Weber PC (1989) A new method using simple solid phase extraction for the rapid gas-chromatographic mass-spectrometric determination of 11- dehydrothromboxane B2 in urine. Prostaglandins 38:157-170
36. Fischer S, von Schacky C, Schweer H (1988) Prostaglandins E3 and F3 alpha are excreted in human urine after ingestion of n-3 polyunsaturated fatty acids. Biochim Biophys Acta 963:501-508
37. Chappell DL, Xiao X, Radziszewski W, Laterza OF (2011) Development and validation of a LC/MS/MS method for 6-keto PGF1a, a metabolite of prostacyclin (PGI2). J Pharm Biomed Anal 56:600-603
38. Fauler J, Tsikas D, Mayatepek E, Keppler D, Frölich JC (1994) Impaired degradation of prostaglandins and thromboxane in Zellweger syndrome. Pediatr Res 36:449-455
39. Balgoma D, Larsson J, Rokach J, Lawson JA, Daham K, Dahlén B, Dahlén SE, Wheelock CE (2013) Quantification of lipid mediator metabolites in human urine from asthma patients by electrospray ionization mass spectrometry: controlling matrix effects. Anal Chem 85:7866-7874
40. Medina S, Domínguez-Perles R, Gil JI, Ferreres F, García-Viguera C, Martínez-Sanz JM, Gil-Izquierdo A (2012) A ultra-pressure liquid chromatography/triple quadrupole tandem mass spectrometry method for the analysis of 13 eicosanoids in human urine and quantitative 24 hour values in healthy volunteers in a controlled constant diet. Rapid Commun Mass Spectrom 26:1249-1257
41. Liu J, Liang Q, Frost-Pineda K, Muhammad-Kah R, Rimmer L, Roethig H, Mendes P, Sarkar M (2011) Relationship between biomarkers of cigarette smoke exposure and biomarkers of inflammation, oxidative stress, and platelet activation in adult cigarette smokers. Cancer Epidemiol Biomarkers Prev 20:1760-1769
42. Zhou Y, Wang ZX, Tang MP, Yao CJ, Xu WJ, Wang LY, Qiao ZD (2010) Nicotine induces cyclooxygenase-2 and prostaglandin E(2) expression in human umbilical vein endothe-lial cells. Int Immunopharmacol 10:461-466