UPLC-ESI-Q-TOF-MSE identification of urinary metabolites of the emerging sport nutrition supplement methoxyisoflavone in human subjects

Journal of Pharmaceutical and Biomedical Analysis

Volumn 96, Issue , 2014, Pages 127-134

  Lecompte, Yannick ^a   Rosset, Martine ^b   Richeval, Camille ^c   Humbert, Luc ^c   Arpino, Patrick ^d  

^a Service de Protection Radiologique des Armees   (France)

^b Service de Santé des Armées État Major de la Marine   (France)

^c LILLE UNIVERSITY HOSPITAL   (France)

^d PSL RESEARCH UNIVERSITY   (France)

Author keywords

5 Methyl 7 methoxyisoflavone; Isoflavones; Mass spectrometry; Metabolism; Urine

Indexed keywords

CARBON DIOXIDE; ISOFLAVONE DERIVATIVE; METHOXYISOFLAVONE; O DEMETHYLASE; PERFORMANCE ENHANCING SUBSTANCE; RADICAL; UNCLASSIFIED DRUG; WATER; 5-METHYL-7-METHOXYISOFLAVONE; FLAVONOID;

ADULT; ARTICLE; DIELS ALDER REACTION; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HUMAN; HYDROLYSIS; HYDROXYLATION; LIQUID LIQUID EXTRACTION; MALE; MIDDLE AGED; POSITIVE ION ELECTROSPRAY; PRIORITY JOURNAL; QUADRUPOLE MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; URINALYSIS; ANALYSIS; DIET SUPPLEMENTATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; PROCEDURES; SPORT; URINE;

ADULT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIETARY SUPPLEMENTS; FEMALE; FLAVONOIDS; HUMANS; ISOFLAVONES; LIQUID-LIQUID EXTRACTION; MALE; MIDDLE AGED; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPORTS;

EID: 84898864976     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2014.03.031     Document Type: Article

References (26)

1. Brennan B.P., Kanayama G., Pope H.G. Performance-enhancing drugs on the web: a growing public-health issue. Am. J. Addict. 2013, 22:158-161.
2. Mason B.C., Lavallee M.E. Emerging supplements in sports. Sports Health 2012, 4:142-146.
3. Heinonen S.M., Wähälä K., Adlercreutz H. Metabolism of isoflavones in human subjects. Phytochem. Rev. 2002, 1:175-182.
4. Koh E., Mitchell A.E. Characterization of urinary isoflavone metabolites excreted after the consumption soy flour or soybean paste using LC-(ESI)MS/MS. J. Food Biochem. 2011, 35:1474-1485.
5. Li H., Wan L., Hashi Y., Chen S. Fragmentation study of a 8-C-glycosyl isoflavone, puerarin, using electrospray ion trap time-of-flight mass spectrometry at high resolution. Rapid Commun. Mass Spectrom. 2007, 21:2497-2504.
6. Madeira P.J., Borges C.M., Florencio M.H. Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric and semi-empirical calculations study of five isoflavone aglycones. Rapid Commun. Mass Spectrom. 2010, 24:3432-3440.
7. Monostory K., Vereczkey L., Lévai F., Szatmári I. Ipriflavone as an inhibitor of human cytochrome P450 enzymes. Br. J. Pharmacol. 1998, 123:605-610.
8. Yoshida K., Tsukamoto T., Torii H., Doi T., Naeshiro I., Uemura I., Tanayama S. Metabolism of ipriflavone (TC-80) in rats. Radioisotopes 1985, 34:612-617.
9. L. Feuer, L. Farkas, M. Nogradi, B. Vermes, A. Gottsegen, A. Wolfner, Metabolic 5-methyl-isoflavone-derivatives, process for the preparation thereof and compositions containing the same, US Patent 4163746 (1979).
10. Kreider R.B., Wilborn C.D., Taylor L., Campbell B., Almada A.L., Collins R., Cooke M., Earnest C.P., Greenwood M., Kalman D.S., Kerksick C.M., Kleiner S.M., Leutholtz B., Lopez H., Lowery L.M., Mendel R., Smith A., Spano M., Wildman R., Willoughby D.S., Ziegenfuss T.N., Antonio J. ISSN exercise and sport nutrition review: research and recommendations. J. Int. Soc. Sports Nutr. 2010, 7:7-50.
11. Incledon T., Van Gammeren D., Antonio J. The effects of 5-methyl-7-methoxyisoflavone on body composition and performance in college-aged men. Med. Sci. Sports Exerc. 2001, 33:S338.
12. Wilborn C.D., Taylor L.W., Campbell B.I., Kerksick C., Rasmussen C.J., Greenwood M., Kreider R.B. Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males. J. Int. Soc. Sports Nutr. 2006, 3:19-27.
13. Lecompte Y., Perrin M., Daude B., Arpino P. Méthoxyisoflavone et dépistage du cannabis dans les urines: mise en évidence d'une réaction croisée peu connue. Ann. Toxicol. Anal. 2012, 24:49-58.
14. Tiller P.R., Yu S., Castro-Perez J., Fillgrove K.L., Baillie T.A. High-throughput, accurate mass liquid chromatography/tandem mass spectrometry on a quadrupole time-of-flight system as a 'first-line' approach for metabolite identification studies. Rapid Commun. Mass Spectrom. 2008, 22:1053-1061.
15. Wu H., Guo J., Chen S., Liu X., Zhou Y., Zhang X., Xu X. Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography-mass spectrometry. J. Pharm. Biomed. Anal. 2013, 72:267-291.
16. French Ministry of Defence Ministerial instruction No. 5549/DEF/CAB on the screening of drug and alcohol abuse applicable to military 2007.
17. Lecompte Y., Perrin M., Salle S., Roussel O. Impact of lowering confirmatory test cutoff value in pre-enlistment urine cannabinoids screening: about five years' experience in the French Gendarmerie. J. Anal. Toxicol. 2012, 36:569-574.
18. Humbert L., Richeval C. Analyse toxicologique avec mesure par « masse exacte ». Caractérisation de métabolites urinaires par couplage UPLC/QTOF: apports et intérêts dans le cadre de la soumission chimique. Ann. Toxicol. Anal. 2012, 24:87-96.
19. Bateman K.P., Castro-Perez J., Wrona M., Shockcor J.P., Yu K., Oballa R., Nicoll-Griffith D.A. MSE with mass defect filtering for in vitro and in vivo metabolite identification. Rapid Commun. Mass Spectrom. 2007, 21:1485-1496.
20. Brenton A.G., Godfrey A.R. Accurate mass measurement: terminology and treatment of data. J. Am. Soc. Mass Spectrom. 2010, 21:1821-1835.
21. Cuyckens F., Claeys M. Mass spectrometry in the structural analysis of flavonoids. J. Mass Spectrom. 2004, 39:1-15.
22. Cuyckens F., Ma Y.L., Pocsfalvi G., Claeysi M. Tandem mass spectral strategies for the structural characterization of flavonoid glycosides. Analusis 2000, 28:888-895.
23. Justino G.C., Borges C.M., Florêncio M.H. Electrospray ionization tandem mass spectrometry fragmentation of protonated flavone and flavonol aglycones: a re-examination. Rapid Commun. Mass Spectrom. 2009, 23:237-248.
24. Kuhn F., Oehme M., Romero F., Abou-Mansour E., Tabacchi R. Differentiation of isomeric flavone/isoflavone aglycones by MS2 ion trap mass spectrometry and a double neutral loss of CO. Rapid Commun. Mass Spectrom. 2003, 17:1941-1949.
25. Fabre N., Rustan I., de Hoffmann E., Quetin-Leclercq J. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2001, 12:707-715.
26. Wu W., Liu Z., Song F., Liu S. Structural analysis of selected characteristic flavones by electrospray tandem mass spectrometry. Anal. Sci. 2004, 20:1103-1105.