Identification and quantification of grapefruit juice furanocoumarin metabolites in urine: An approach based on ultraperformance liquid chromatography coupled to linear ion trap-orbitrap mass spectrometry and solid-phase extraction coupled to ultraperformance liquid chromatography coupled to triple quadrupole-tandem mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 9, 2014, Pages 2134-2140

  Regueiro, Jorge ^a   Vallverdú Queralt, Anna ^b,c   Negreira, Noelia ^d   Simal Gándara, Jesús ^a   Lamuela Raventós, Rosa M ^b,c  

^a UNIVERSITY OF VIGO   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c Instituto de Salud Carlos III   (Spain)

^d INSTITUTE OF ENVIRONMENTAL ASSESSMENT AND WATER RESEARCH   (Spain)

Author keywords

bergaptol; biomarker; furanocoumarins; grapefruit; UPLC LTQ Orbitrap; urine

Indexed keywords

BERGAPTOL; FURANOCOUMARINS; GRAPEFRUIT; UPLC-LTQ-ORBITRAP; URINE; LTQ ORBITRAP;

BIOMARKERS; BIOMOLECULES; BODY FLUIDS; CHROMATOGRAPHY; DRUG INTERACTIONS; EXTRACTION; HIGH PRESSURE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; PHASE SEPARATION; CITRUS FRUITS; LIQUID CHROMATOGRAPHY; LIQUIDS; SPECTROMETRY;

CITRUS FRUITS; EXTRACTION;

PSORALEN DERIVATIVE;

ADULT; ARTICLE; CHEMISTRY; EVALUATION STUDY; GRAPEFRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOLATION AND PURIFICATION; MALE; METABOLISM; METHODOLOGY; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; URINE; YOUNG ADULT;

ADULT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS PARADISI; HUMANS; MALE; PSORALENS; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; YOUNG ADULT;

CITRUS LIMON; CITRUS X PARADISI;

EID: 84897725966     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf405701a     Document Type: Article

References (23)

1. Chaudhary, P. R.; Jayaprakasha, G. K.; Patil, B. S.; Porat, R. Grapefruit degreening influence on health promoting limonoids and flavonoids Acta Hortic. 2012, 939, 113-120
2. Chebrolu, K. K.; Jayaprakasha, G. K.; Jifon, J.; Patil, B. S. Production system and storage temperature influence grapefruit vitamin C, limonoids, and carotenoids J. Agric. Food Chem. 2012, 60, 7096-7103
3. Miller, E. G.; Peacock, J. J.; Bourland, T. C.; Taylor, S. E.; Wright, J. M.; Patil, B. S.; Miller, E. G. Inhibition of oral carcinogenesis by citrus flavonoids Nutr. Cancer 2008, 60, 69-74
4. Vanamala, J.; Leonardi, T.; Patil, B. S.; Taddeo, S. S.; Murphy, M. E.; Pike, L. M.; Chapkin, R. S.; Lupton, J. R.; Turner, N. D. Suppression of colon carcinogenesis by bioactive compounds in grapefruit Carcinogenesis 2006, 27, 1257-1265
5. Keevil, J. G.; Osman, H. E.; Reed, J. D.; Folts, J. D. Grape juice, but not orange juice or grapefruit juice, inhibits human platelet aggregation J. Nutr. 2000, 130, 53-56
6. Gorinstein, S.; Caspi, A.; Libman, I.; Lerner, H. T.; Huang, D.; Leontowicz, H.; Leontowicz, M.; Tashma, Z.; Katrich, E.; Feng, S.; Trakhtenberg, S. Red grapefruit positively influences serum triglyceride level in patients suffering from coronary atherosclerosis: Studies in vitro and in humans J. Agric. Food Chem. 2006, 54, 1887-1892
7. Lian-Qing, G.; Fukuda, K.; Ohta, T.; Yamazoe, Y. Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity Drug Metab. Dispos. 2000, 28, 766-771
8. Schmiedlin-Ren, P.; Edwards, D. J.; Fitzsimmons, M. E.; He, K.; Lown, K. S.; Woster, P. M.; Rahman, A.; Thummel, K. E.; Fisher, J. M.; Hollenberg, P. F.; Watkins, P. B. Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents: Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins Drug Metab. Dispos. 1997, 25, 1228-1233
9. Seden, K.; Dickinson, L.; Khoo, S.; Back, D. Grapefruit-drug interactions Drugs 2010, 70, 2373-2407
10. Edwards, D. J.; Bellevue, F. H.; Woster, P. M. Identification of 6′,7′-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice Drug Metab. Dispos. 1996, 24, 1287-1290
11. Ohta, T.; Miyamoto, Y.; Maruyama, T.; Kiuchi, F.; Tsukamoto, S. Localization and contents of paradisins, the most potent CYP3A4 inhibitors, in grapefruit Citrus paradisii and grapefruit juice Nat. Med. 2002, 56, 264-267
12. Girennavar, B.; Poulose, S. M.; Jayaprakasha, G. K.; Bhat, N. G.; Patil, B. S. Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes Bioorg. Med. Chem. 2006, 14, 2606-2612
13. Messer, A.; Nieborowski, A.; Strasser, C.; Lohr, C.; Schrenk, D. Major furocoumarins in grapefruit juice I: Levels and urinary metabolite(s) Food Chem. Toxicol. 2011, 49, 3224-3231
14. Manthey, J. A.; Buslig, B. S. Distribution of furanocoumarins in grapefruit juice fractions J. Agric. Food Chem. 2005, 53, 5158-5163
15. De Castro, W. V.; Mertens-Talcott, S.; Rubner, A.; Butterweck, V.; Derendorf, H. Variation of flavonoids and furanocoumarins in grapefruit juices: A potential source of variability in grapefruit juice-drug interaction studies J. Agric. Food Chem. 2006, 54, 249-255
16. Girennavar, B.; Jayaprakasha, G. K.; Jifon, J. L.; Patil, B. S. Variation of bioactive furocoumarins and flavonoids in different varieties of grapefruits and pummelo Eur. Food Res. Technol. 2008, 226, 1269-1275
17. Girennavar, B.; Jayaprakasha, G. K.; Patil, B. S. Influence of pre-and post-harvest factors and processing on the levels of furocoumarins in grapefruits (Citrus paradisi Macfed.) Food Chem. 2008, 111, 387-392
18. Trontelj, J. Quantification of glucuronide metabolites in biological matrices by LC-MS/MS. In Tandem Mass Spectrometry-Applications and Principles; Prasain, D. J., Ed.; InTech: Rijeka, Croatia, 2012.
19. Zhang, J.; Brodbelt, J. S. Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS Analyst 2004, 129, 1227-1233
20. Erlund, I.; Meririnne, E.; Alfthan, G.; Aro, A. Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice J. Nutr. 2001, 131, 235-241
21. 2: Enhancing chromatographic quantification and application in Caco-2 cell metabolism J. Pharm. Biomed. Anal. 2011, 55, 1245-1254
22. Fontanals, N.; Marcé, R. M.; Borrull, F.; Cormack, P. A. G. Mixed-mode ion-exchange polymeric sorbents: Dual-phase materials that improve selectivity and capacity TrAC, Trends Anal. Chem. 2010, 29, 765-779
23. Strahm, E.; Rudaz, S.; Veuthey, J.-L.; Saugy, M.; Saudan, C. Profiling of 19-norsteroid sulfoconjugates in human urine by liquid chromatography mass spectrometry Anal. Chim. Acta 2008, 613, 228-223