A new LC/MS/MS rapid and sensitive method for the determination of green tea catechins and their metabolites in biological samples

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 22, 2007, Pages 8857-8863

  Mata Bilbao, Maria De Lourdes ^a   Andrés Lacueva, Cristina ^a   Roura, Elena ^a   Jáuregui, Olga ^a   Torre, Celina ^b   Lamuela Raventós, Rosa Maria ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b Affinity Petcare   (Spain)

Author keywords

Absorption; Flavonoids; Green tea; Metabolites

Indexed keywords

CATECHIN; DRUG DERIVATIVE; EPICATECHIN GALLATE; EPIGALLOCATECHIN GALLATE; GLUCURONIDE;

ANIMAL; ARTICLE; BLOOD; CHEMISTRY; DOG; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; TEA; URINE;

ANIMALS; CATECHIN; CHROMATOGRAPHY, LIQUID; DOGS; GLUCURONIDES; MASS SPECTROMETRY; TEA;

EID: 36148996902     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0713962     Document Type: Article

References (52)

1. Kris-Etherton, P. M.; Keen, C. L. Evidence that the antioxidant flavonoids in tea and cocoa are beneficial for cardiovascular health. Curr. Opin. Lipidol. 2002, 13, 41-49.
2. Rimm, E. B.; Stampfer, M. Diet, Lifestyle, and Longevity - The Next Steps. JAMA 2004, 292, 1490-1492.
3. Zaveri, N. T. Green tea and its polyphenolic catechins: Medicinal uses in cancer and noncancer applications. Life Sci. 2006, 78, 2073-2080.
4. Cooper, R.; Morre, D. J.; Morre, D. M. Medicinal benefits of green tea: Part I. Review of noncancer health benefits. J. Altern. Complement. Med. 2005, 11, 521-528.
5. Frei, B.; Higdon, J. V. Antioxidant Activity of tea polyphenols in vivo: Evidence from animal studies. J. Nutr. 2003, 133, 3275S-3284S.
6. Bettuzi, S.; Brausi, M.; Rizzi, F.; Castagnetti, G.; Peracchia, G.; Corti, A. Chemoprevention of human prostate cancer by oral administration of green tea catechins in volunteers with high-grade prostate intraepithelial neoplasia: A preliminary report from a one-year proof-of-principle study. Cancer Res. 2006, 66, 1234-1240.
7. Yoshikazu, S.; Haruo, N.; Takao, W.; Shigeru, H.; Hiroyuki, S.; Susumu, F.; Yoshimi, I.; Yasuo, I.; Seiki, S.; Kunio, K.; Masayuki, I. Possible contribution of green tea drinking habits to the prevention of stroke. Tohoku J. Exp. Med. 1989, 157, 337-343.
8. Nakachi, K.; Matsuyama, S.; Miyake, S.; Suganuma, M.; Imai, K. Preventive effects of drinking green tea on cancer and cardiovascular disease: Epidemiological evidence for multiple targeting prevention. Biofactors 2000, 13, 49-54.
9. Iwai, N.; Ohshiro, H.; Kurozawa, Y.; Hosoda, T.; Morita, H.; Funakawa, K.; Okamoto, M.; Nose, T. Relationship between coffee and green tea consumption and all-cause mortality in a cohort of a rural Japanese population. J. Epidemiol. 2002, 12, 191-198.
10. Nakachi, K.; Eguchi, H.; Imai, K. Can teatime increase one's lifetime. Ageing Res. Rev. 2003, 2, 1-10.
11. Kuriyama, S.; Shimazu, T.; Ohmori, K.; Kikuchi, N.; Nakaya, N.; Nishino, Y.; Tsubono, Y.; Tsuji, I. Green tea consumption and mortality due to cardiovascular disease, cancer, and all causes in Japan: The Ohsaki Study. JAMA 2006, 296, 1255-65.
12. Graham, H. N. Green tea composition, consumption, and polyphenol chemistry. Prev. Med. 1992, 21, 334-350.
13. Day, A. J.; Mellon, F.; Barron, D.; Sarrazin, G.; Morgan, M. R. A.; Williamson, G. Human metabolism of dietary flavonoids: Identification of plasma metabolites of quercetin. Free Radic. Res. 2001, 35, 941-952.
14. Day, A. J.; Williamson, G. Biomarkers of exposure to dietary flavonoids a review of the current evidence for the identification of quercetin glycosides in plasma. Br. J.Nutr. 2001, 86, S105-S110.
15. Graefe, E. U.; Wittig, J.; Mueller, S.; Riethling, A. K.; Uehleke, B.; Drewelow, B.; Pforte, H.; Jacobasch, G.; Derendorf, H.; Veit, M. Pharmacokinetics and bioavailability of quercetin glycosides in humans. J. Clin. Pharmacol. 2001, 41, 492-499.
16. Natsume, M.; Osakabe, N.; Oyama, M.; Sasaki, M.; Baba, S.; Nakamura, Y.; Osawa, T.; Terao, J. Structures of (-)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (-)-epicatechin: Differences between human and rat. Free Radic. Biol. Med. 2003, 34, 840-849.
17. Zhang, Y.; Hendrich, S.; Murphy, P. A. Glucuronides are the main isoflavone metabolites in women. J. Nutr. 2003, 133, 399-404.
18. Kroon, P. A.; Clifford, M. N.; Crozier, A.; Day, A. J.; Donovan, J. L.; Manach, C.; Williamson, G. How should we assess the effects of exposure to dietary polyphenols in vitro? Am. J. Clin. Nutr. 2004, 80, 15-21.
19. Roura, E.; Andres-Lacueva, C.; Jauregui, O.; Badia, E.; Estruch, R.; Izquierdo-Pulido, M.; Lamuela-Raventos, R. M. Rapid liquid chromatography tandem mass spectrometry assay to quantify plasma (-)-epicatechin metabolites after ingestion of a standard portion of cocoa beverage in humans. J. Agric. Food Chem. 2005, 53, 6190-6194.
20. Harada, M.; Kan, Y.; Naoki, H.; Fukui, Y.; Kageyama, N.; Kiso, W. Identification of the major antioxidative metabolites in biological fluids of the rat with ingested (+)-catechin and (-)-epicatechin. Biosci. Biotechnol. Biochem. 1999, 63, 973-977.
21. Spencer, J. P.; Schroeter, H.; Rice-Evans, C. Epicatechin and its in vivo metabolite, 3′-O-methyl epicatechin, protect human fibroblasts from oxidative-stress-induced cell death involving caspase-3 activation. Biochemistry 2001, 354, 493-500.
22. Osborne, R.; Joel, S.; Trew, D.; Slevin, M. Analgesic activity of morphine-6-glucuronide. Lancet 1988, 8589, 828.
23. Paul, D.; Standifer, K. M.; Inturrisi, C. E.; Pasternak, G. W. Pharmacological characterization of morphine-6 beta-glucuronide, a very potent morphine metabolite. J. Pharmacol. Exp. Ther. 1989, 251, 477-483.
24. Osborne, R.; Thompson, P.; Joel, S.; Trew, D.; Patel, N.; Slevin, M. The analgesic activity of morphine-6-glucuronide. Br. J. Clin. Pharmacol. 1992, 34, 130-138.
25. Zhang, Y.; Song, T. T.; Cunnick, J. E.; Murphy, P. A.; Hendrich, S. Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations. J. Nutr. 1999, 129, 399-495.
26. Spencer, P. E.; Schroeter, H.; Crossthwaithe, A. J.; Kuhnle, G.; Williams, R. J.; Rice-Evans, C. Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic. Biol. Med. 2001, 31, 1139-1146.
27. Okushio, K.; Suzuki, M.; Matsumoto, N.; Nanjo, F.; Hara, Y. Identification of (-)-epicatechin metabolites and their metabolic fate in the rat. Drug Metab. Dispos. 1999, 27, 309-316.
28. Harada, M.; Kan, Y.; Naoki, H.; Fukui, Y.; Kageyama, N.; Nakai, M.; Miki, W.; Kiso, Y. Identification of the major antioxidative metabolites in biological fluids of the rat with ingested (+)-catechin and (-)-epicatechin. Biosci. Biotechnol. Biochem. 1999, 63, 973-977.
29. Unno, T.; Sagesaka, Y. M.; Kakuda, T. J. Analysis of tea catechins in human plasma by high-performance liquid chromatography with solid-phase extraction. J. Agric. Food Chem. 2005, 53, 9885-9889.
30. Henning, S. M.; Niu, Y.; Liu, Y.; Lee, N. H.; Hara, Y.; Thames, G. D.; Minutti, R. R.; Carpenter, C. L.; Wang, H.; Heber, D. Bioavailability and antioxidant effect of epigallocatechin gallate administered in purified form versus as green tea extract in healthy individuals. J. Nutr. Biochem. 2005, 16, 610-616.
31. Lee, M. J.; Maliakal, P.; Chen, L.; Meng, X.; Bondoc, F.; Prabhu, S.; Lambert, G.; Mohr, S.; Yang, C. Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: formation of different metabolites and individual variability. Cancer Epidemiol. Biomark. Prev. 2002, 11, 1025-1032.
32. Chow, H. H.; Cai, Y.; Alberts, D. S.; Hakim, I.; Dorr, R.; Shahi, F.; Crowell, J. A.; Yang, C. S.; Hara, Y. Phase I Pharmacokinetic Study of Tea Polyphenols following Single-dose Administration of Epigallocatechin Gallate and Polyphenon E. Cancer Epidemiol. Biomark Prev. 2001, 10, 53-58.
33. Lee, M. J.; Wang, X. Y.; Li, H.; Chen, L.; Sun, Y.; Gobbo, S.; Balentine, D. A.; Yang, C. S. Analysis of Plasma and Urinary tea Polyphenols in Human Subjects. Cancer Epidemiol., Biomarkers Prev. 1995, 4, 393-399.
34. van Amelsvoort, J. M.; van het Hof, K. H.; Mathot, J. N. J. J.; Mulder, T. P. J.; Wiersma, A.; Tijnerg, L. B. M. Plasma concentrations of individual tea catechins after a single oral dose in humans. Xenobiotica 2001, 31, 891-901.
35. Yang, C. S.; Chen, L.; Lee, M. J.; Balentine, D.; Kuo, M. C.; Schatz, S. P. Blood and urine levels of tea catechins after ingestion of different amounts of green tea by human volunteers. Cancer Epidemiol., Biomarkers Prev. 1998, 7, 351-354.
36. Maiani, G.; Serafini, M.; Salucci, M.; Azzini, E.; Ferreo-Luzzi, A. Application of a new high-performance liquid chromatographic method for measuring selected polyphenols in human plasma. J. Chromatogr. B. 1997, 692, 311-317.
37. Pietta, P.; Simonetti, P.; Gardana, C.; Brusamolino, A.; Morazoni, P.; Bombardelli, E. Catechin metabolites after intake of green tea infusions. Biochem. Mol. Biol. Int. 1998, 46, 895-903.
38. Lee, M. J.; Prabhu, S.; Meng, X.; Li, C.; Yang, C. S. Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: formation of different metabolites and individual variability. Anal. Biochem. 2000, 279, 164-169.
39. Kotani, A.; Miyashita, N.; Kusu, F. Determination of catechins in human plasma after commercial canned green tea ingestion by high-performance liquid chromatography with electrochemical detection using a microbore column. J. Chromatogr. B. 2003, 788, 269-275.
40. Umegaki, K.; Sugisawa, A.; Yamada, K.; Higuchi, M. Analytical method of measuring tea catechins in human plasma by solid-phase extraction and HPLC with electrochemical detection. J. Nutr. Sci. Vitaminol. 2001, 47, 402-408.
41. Nakagawa, K.; Miyazawa, T. Chemiluminescence-high-performance liquid chromatographic determination of tea catechin, (-)-epigallocatechin 3-gallate, at picomole levels in rat and human plasma. Anal. Biochem. 1997, 248, 41-49.
42. Masukawa, Y.; Matsui, Y.; Shimizu, N.; Kondou, N.; Endou, H.; Kuzukawa, M.; Hase, T. Determination of green tea catechins in human plasma using liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. B. 2006, 834, 26-34.
43. Murphy, A. T.; Bonate, P. L.; Kasper, S. C.; Gillespie, T. A.; Delong, A. F. Determination of xanomeline in human plasma by ionspray tandem mass-spectrometry. Mass Spectrom. 1994, 23, 621-625.
44. Mata, M. L.; Lacueva, C. A.; Roura, E.; Jáuregui, O.; Escribano, E.; Torre, C.; Lamuela-Raventós, R. M. Absorption and pharmacokinetics of grapefruit flavanones in beagles. Br. J. Nutr. 2007, 98, 86-92.
45. Urpí-Sardà, M.; Jáuregui, O.; Lamuela- Raventós, R. M.; Jaeger, W.; Miksits, M.; Covas, M. I.; Andrés-Lacueva, C. Uptake of diet resveratrol into the human low-density lipoprotein. Identification and quantification of resveratrol metabolites by liquid chromatography coupled with tandem mass spectrometry. Anal. Chem. 2005, 77, 3149-3155.
46. Committee on care and use of laboratory animals. Guide for the Care and Use of Laboratory Animals; Institute of Laboratory Animals Resources, National Research Council: Washington, DC, 1985; 83 pp.
47. Gonthier, M. P.; Rios, L. Y.; Verny, M. A.; Remesy, C.; Scalbert, A. Novel liquid chromatography-electrospray ionization mass spectrometry method for the quantification in human urine of microbial aromatic acid metabolites derived from dietary polyphenols. J. Chromatogr., B 2003, 789, 243-255.
48. Kiser, M.; Dolan, J. W. Selecting the Best Curve Fit. LC-GC Eur. 2004, 17, 138-143.
49. U. S. Department of Health and Human Services, Food and Drug Administration. Guidance for Industry. Bioanalytical Method Validation; Washington, DC, 2001.
50. Nobilis, M.; Holcapek, M.; Kolárová, L.; Kopecky, J.; Kunes, M.; Svoboda, Z.; Kvetina, J. Identification and determination of phase II nabumetone metabolites by high-performance liquid chromatography with photodiode array and mass spectrometric detection. J. Chromatogr., A. 2004, 1031, 229-236.
51. Li, C.; Meng, X.; Winnik, B.; Lee, M.; Lu, H.; Sheng, S.; Buckley, B.; Yang, C. S. Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry. Chem. Res. Toxicol. 2001, 14, 702-707.
52. Meng, X.; Sang, S.; Zhu, N.; Lu, H.; Sheng, S.; Lee, M.; Ho, C.; Yang, C. S. Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats. Chem. Res. Toxicol. 2002, 15, 1042-1050.