New UHPLC-QqQ-MS/MS method for quantitative and qualitative determination of free phytoprostanes in foodstuffs of commercial olive and sunflower oils

Food Chemistry

Volumn 178, Issue , 2015, Pages 212-220

  Collado González, Jacinta ^a   Medina, Sonia ^a   Durand, Thierry ^b   Guy, Alexandre ^b   Galano, Jean Marie ^b   Torrecillas, Arturo ^c   Ferreres, Federico ^a   Gil Izquierdo, Angel ^a  

^a UNIVERSITY OF MURCIA   (Spain)

^b UNIVERSITÉ DE MONTPELLIER   (France)

^c RESEARCH GROUP ON QUALITY   (Spain)

Author keywords

Mass spectrometry; Olive oil; Phytoprostanes; Sunflower oil; UHPLC

Indexed keywords

MANUFACTURE; MASS SPECTROMETRY; OIL SHALE; OILS AND FATS; OLIVE OIL;

ACCURATE ANALYTICAL METHODS; EXTRA VIRGIN OLIVE OIL; EXTRACTION EFFICIENCIES; INTER-DAY VARIATIONS; MANUFACTURE PROCESS; PHYTOPROSTANES; TARGET COMPOUND; UHPLC;

SUNFLOWER OIL;

EXTRA VIRGIN OLIVE OIL; OLIVE OIL; PHYTOPROSTANE DERIVATIVE; PLANT MEDICINAL PRODUCT; PROSTANOID; SUNFLOWER OIL; UNCLASSIFIED DRUG;

ANALYTICAL PARAMETERS; ARTICLE; CONTROLLED STUDY; FOOD; FOOD PROCESSING; LIMIT OF DETECTION; LIMIT OF QUANTITATION; MEASUREMENT ACCURACY; MEASUREMENT PRECISION; QUADRUPOLE MASS SPECTROMETRY; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; TANDEM MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; VALIDATION STUDY;

HELIANTHUS;

EID: 84944652842     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2015.01.097     Document Type: Article

References (42)

1. A.H. Abuznait, H. Qosa, B.A. Busnena, K.A. El Sayed, and A. Kaddoumi Olive-oil-derived oleocanthal enhances β-amyloid clearance as a potential neuroprotective mechanism against Alzheimer's disease: In vitro and in vivo studies ACS Chemical Neuroscience 4 6 2013 973 982
2. A.E. Barden, K.D. Croft, T. Durand, A. Guy, and M.J. Mueller Flaxseed oil supplementation increases plasma F1-phytoprostanes in healthy men The Journal of Nutrition 139 10 2009 1890 1895
3. G.K. Beauchamp, R.S. Keast, D. Morel, J. Lin, J. Pika, and Q. Han Phytochemistry: Ibuprofen-like activity in extra-virgin olive oil Nature 437 7055 2005 45 46
4. V. Cavalca, F. Minardi, S. Scurati, F. Guidugli, I. Squellerio, and F. Veglia Simultaneous quantification of 8-iso-prostaglandin-F2a and 11-dehydro thromboxane B2 in human urine by liquid chromatography-tandem mass spectrometry Analytical Biochemistry 397 2010 168 174
5. Codex Alimentarius. (2009). CODEX STAN 33-1981.Rev. 2-2003. Codex standard for olive oils and olive pomace oils. Commission of the Codex Alimentarius. pp. 1-8.
6. M.H. Cruz de Carvalho Drought stress and reactive oxygen species: Production, scavenging and signaling Plant Signaling & Behavior 3 3 2008 156 165
7. C.A. De la Lastra, M.D. Barranco, V. Motilva, and J.M. Herrerias Mediterranean diet and health: Biological importance of olive oil Current Pharmaceutical Design 7 10 2001 933 950
8. M. Del Carlo, E. Ritelli, G. Procida, F. Murmura, and A. Cichelli Characterization of extra virgin olive oils obtained from different cultivars Pomologia Croatica 12 2006 29 41
9. T. Durand, V. Bultel-Poncé, A. Guy, S. Berger, M. Mueller, and J.-M. Galano New bioactive oxylipins formed by non-enzymatic free-radical-catalyzed pathways: The phytoprostanes Lipids 44 10 2009 875 888
10. N. Eckardt Oxylipin signaling in plant stress responses Plant Cell 20 3 2008 495 497
11. S. El Fangour, A. Guy, V. Despres, J.-P. Vidal, J.-C. Rossi, and T. Durand Total syntheses of the eight diastereoisomers of the syn-anti-syn phytoprostanes F1 types I an II The Journal of Organic Chemistry 69 7 2004 2498 2503
12. S. El Fangour, A. Guy, J.-P. Vidal, J.-C. Rossi, and T. Durand A flexible synthesis of the phytoprostanes B1 Type I and II The Journal of Organic Chemistry 70 3 2005 989 997
13. I. Fki, N. Allouche, S. Sayadi, N. Fki, and S. Allouche The use of polyphenolic extract, purified hydroxytyrosol and 3,4-dihydroxyphenyl acetic acid from olive mill wastewater for the stabilization of refined oils: A potential alternative to synthetic antioxidants Food Chemistry 93 2 2005 197 204
14. Food and Agriculture Organization of the United Nations (FAO). (1997). Grasas y aceites en la nutrición humana. Consulta FAO/OMS expertos. Version 57. In: FAO food and nutrition papers (Vol. V4700). Roma. Available < http:// www.fao.org/docrep/v4700s/4700s00.htm >. Accessed 10.09.13.
15. C. Göbel, and I. Feussner Methods for the analysis of oxylipins in plants Phytochemistry 70 13-14 2009 1485 1503
16. J. Gutermuth, M. Bewersdorff, C. Traidl-Hoffmann, J. Ring, M.J. Mueller, and H. Behrendt Immunomodulatory effects of aqueous birch pollen extracts and phytoprostanes on primary immune responses in vivo Journal of Allergy and Clinical Immunology 120 2 2007 293 299
17. J.L. Harwood, and P. Yaqoob Nutritional and health aspects of olive oil European Journal of Lipid Science and Technology 104 9-10 2002 685 697
18. R. Imbusch, and M.J. Mueller Analysis of oxidative stress and wound-inducible dinor isoprostanes F(1) (phytoprostanes F(1)) in plants Plant Physiology 124 3 2000 1293 1303
19. R. Imbusch, and M.J. Mueller Formation of isoprostane F(2)-like compounds (phytoprostanes F(1)) from alpha-linolenic acid in plants Free Radical Biology & Medicine 28 5 2000 720 726
20. International Conference on Harmonization (ICH). (1994). Validation of analytical method: Definitions and terminology. ICH Q2A, Geneva.
21. International Olive Oil Council. (2012). Olive oil and health. World olive oil figures (Vol. November, 2012). Available < http://www.internationaloliveoil.org/estaticos/view/131-world-olive-oil-figures > Accessed 8.09.13.
22. U. Jahn, J.-M. Galano, and T. Durand Beyond prostaglandins - Chemistry and biology of cyclic oxygenated metabolites formed by free-radical pathways from polyunsaturated fatty acids Angewandte Chemie International Edition 47 32 2008 5894 5955
23. U. Jahn, J.-M. Galano, and T. Durand A cautionary note on the correct structure assignment of phytoprostanes and the emergence of a new prostane ring system Prostaglandins Leukotrienes and Essential Fatty Acids 82 2-3 2010 83 86
24. K. Karg, V. Dirsch, A.M. Vollmar, J.-L. Cracowski, F. Laporte, and M.J. Mueller Biologically active oxidized lipids (phytoprostanes) in the plant diet and parenteral lipid nutrition Free Radical Research 41 1 2007 25 37
25. P. Kris-Etherton, K. Hecker, and A. Binkoski Polyunsaturated fatty acids and cardiovascular health Nutrition Reviews 62 11 2004 414 426
26. C. Loeffler, S. Berger, A. Guy, T. Durand, G. Bringmann, and M. Dreyer B1-phytoprostanes trigger plant defense and detoxification responses Plant Physiology 137 1 2005 328 340
27. B.K. Matuszewski, M.L. Constanzer, and C.M. Chavez-Eng Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS Analytical Chemistry 75 13 2003 3019 3030
28. S. Medina, R. Dominguez-Perles, J.I. Gil, F. Ferreres, C. Garcia Viguera, and J.M. Martínez-Sanz 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 Communications in Mass Spectrometry 26 10 2012 1249 1257
29. Melgarejo, M. (2003). Asagir. Girasol/Usos. Informative booklet number 3. Available < http:// www.Asagir.org.ar/cuad-4.pdf >. Accessed 8.09.13.
30. J.D. Morrow, K.E. Hill, R.F. Burk, T.M. Nammour, K.F. Badr, and L.J. Roberts A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism Proceedings of the National academy of Sciences of the United States of America 87 23 1990 9383 9387
31. M.J. Mueller Archetype signals in plants: The phytoprostanes Current Opinion in Plant Biology 7 4 2004 441 448
32. D.H. Nugteren, H. Vonkeman, and D.A. Vandorp Non-enzymatic conversion of all cis 8,11,14-eicosatrienoic acid into prostaglandin E1 Recueil des Travaux Chimiques des Pays-Bas 86 11 1967 1237 1245
33. S. Parchmann, and M.J. Mueller Evidence for the formation of dinor isoprostanes E1 from alpha-linolenic acid in plants Journal of Biological Chemistry 273 49 1998 32650 32655
34. E. Pinot, A. Guy, A. Fournial, L. Balas, J.-C. Rossi, and T. Durand Total synthesis of the four enantiomerically pure diasteroisomers of the phytoprostanes E1Type II and of the 15-E2t-isoprostanes Journal of Organic Chemistry 73 8 2008 3063 3069
35. W.A. Pryor, E. Blair, and J.P. Stanley Autoxidation of polyunsaturated fatty acids: II. A suggested mechanism for the formation of TBA-reactive materials from prostaglandin-like endoperoxides Lipids 11 5 1976 370 379
36. C.H.S. Ruxton, S.C. Reed, M.J.A. Simpson, and K.J. Millington The health benefits of omega-3 polyunsaturated fatty acids: A review of the evidence Journal of Human Nutrition & Dietetics 17 5 2004 449 459
37. S.E. Sattler, L. Mène Saffrané, E.E. Farmer, M. Krischke, M.J. Mueller, and D. DellaPenna Nonenzymatic lipid peroxidation reprograms gene expression and activates defense markers in Arabidopsis tocopherol-deficient mutants Plant Cell 18 12 2006 3706 3720
38. A. Stark, and Z. Madar Olive oil as a functional food: Epidemiology and nutritional approaches Nutrition Reviews 60 6 2002 170 176
39. The US Food and Drug Administration (FDA). Department of Health and Human Sercices. (2001). Guidance for industry: Bioanalytical method validation. Available < http://www.fda.gov/cder/guidance>. Accessed 10.09.13.
40. I. Thoma, M. Krischke, C. Loeffler, and M.J. Mueller The isoprostanoid pathway in plants Chemistry and Physics of Lipids 128 1-2 2004 135 148
41. I. Thoma, C. Loeffler, A.K. Sinha, M. Gupta, M. Krischke, and B. Steffan Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants Plant Journal 34 3 2003 363 375
42. A. Vazquez Romero, X. Verdaguer, and A. Riera General approach to prostanes B1 by intermolecular Pauson-Khand reaction: Syntheses of methyl esters of prostaglandin B1and phytoprostanes 16-B1-PhytoP and 9-L1-PhytoP European Journal of Organic Chemistry 2013 9 2013 1716 1725