Conversion L-tryptophan to melatonin in the gastrointestinal tract: The new high performance liquid chromatography method enabling simultaneous determination of six metabolites of L-tryptophan by native fluorescence and UV-VIS detection

Journal of Physiology and Pharmacology

Volumn 63, Issue 6, 2012, Pages 613-621

  Zagajewski, J ^a   Drozdowicz, D ^a   Brzozowska, I ^a   Hubalewska Mazgaj, M ^a   Stelmaszynska, T ^a   Laidler, P M ^a   Brzozowski, T ^a  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

Author keywords

5 hydroxytryptamine; 5 hydroxytryptophan; Antranilic acid; Gastrointestinal tract; Indoleacetic acid; Kynurenine; L tryptophan; Melatonin; Melatonin metabolites

Indexed keywords

5 HYDROKSYTRYPTOPHAN; AMINO ACID; ANTRANILIC ACID; INDOLEACETIC ACID; KYNURENINE; MELATONIN; METHANOL; SEROTONIN; TRIFLUOROACETIC ACID; TRYPTOPHAN; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AMINO ACID ANALYSIS; AMINO ACID BLOOD LEVEL; AMINO ACID METABOLISM; ARTICLE; CONTROLLED STUDY; ELUTION; FEMALE; FLUORESCENCE ANALYSIS; GASTROINTESTINAL TRACT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; PRECIPITATION; PROCESS DEVELOPMENT; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET RADIATION;

5-HYDROXYTRYPTOPHAN; ADMINISTRATION, ORAL; ANIMALS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; GASTROINTESTINAL TRACT; INDOLEACETIC ACIDS; KYNURENINE; MALE; MELATONIN; RATS; RATS, WISTAR; SEROTONIN; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TRYPTOPHAN;

EID: 84873425786     PISSN: 08675910     EISSN: 18991505     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. Konturek SJ, Konturek PC, Brzozowski T, Bubenik GA. Role of melatonin in upper gastrointestinal tract. J Physiol Pharmacol 2007; 58(Suppl. 6): 23-52.
2. Shibata K, Fukuwatari T. The metabolites in the tryptophan degradation pathway might be useful to determine the tolerable upper intake level of tryptophan intake in rats. J Nutr 2012; 142: 2227S-2230S.
3. Stone TW, Stoy N, Darlington LG. An expanding range of targets for kynurenine metabolites of tryptophan. Trends Pharmacol Sci 2012; Oct 31: doi: 10.1016/j.tips. 2012.09.006. [Epub ahead of print].
4. Reiter RJ, Richardson BA, Hurlbut EC. Pineal, retinal and Harderian gland melatonin in a diurnal species, the Richardson's ground squirrel (Spermophilus richardsonii). Neurosci Lett 1981; 22: 285-288.
5. Fukuhara C, Liu C, Ivanova TN, et al. Gating of the cAMP signaling cascade and melatonin synthesis by the circadian clock in mammalian retina. J Neurosci 2004; 24: 1803-1811.
6. Raikhlin NT, Kvetnoy IM, Tolkachev VN. Melatonin may be synthetized in enterochromaffine cells. Nature 1975; 255: 344-345.
7. Huether G, Poeggeler B, Reimer A, George A. Effects of tryptophan administration on circulating melatonin levels in chicks and rats: evidence for stimulation of melatonin synthesis and release in the gastrointestinal tract. Life Sci 1992; 51: 945-953.
8. Bubenik GA. Gastrointestinal melatonin, localization, function and clinical relevance. Dig Dis Sci 2002; 10: 2336-2348.
9. Bubenik GA, Hacker RR, Brown GM, Bartos L. Melatonin concentrations in the luminal fluid, mucosa, and muscularis of the bovine and porcine gastrointestinal tract. J Pineal Res 1999; 26: 56-63.
10. Tan DX, Manchester LC, Reiter RJ, Qi W, Hanes MA, Farley NJ. High physiological level of melatonin in the bile of mammals. Life Sci 1999; 65: 2523-2529.
11. Bubenik G. Pinealectomy reduces melatonin levels in the serum, but not in the gastrointestinal tract of the rat. Biol Signals 1977; 6: 40-44.
12. Messner M, Huether G, Lorf T, Ramadori G, Schworer H. Presence of melatonin in the human hepatobiliarygastrointestinal tract. Life Sci 2001; 69: 543-551.
13. Duffy JF, Dijk DJ, Hall EF, Czeisle CA. Relationship of endogenous circadian melatonin and temperature rhythms to self-reported preference for morning or evening activity in young and old people. J Invest Med 1999; 47: 141-150.
14. Zhang X, He Y, Ding M. Simultaneous determination of tryptophan and kynurenine in plasma samples of children patients with Kawasaki disease by high-performance liquid chromatography with programmed wavelength ultraviolet detection. J Chromatogr B Analyt Technol Biomed Life Sci 2009; 877: 1678-1682.
15. Herve C, Beyne P, Jamault H, Delacoux E. Determination of tryptophan and its kynurenine pathway metabolites in human serum by high-performance liquid chromatography with simultaneous ultraviolet and fluorimetric detection. J Chromatogr B Biomed Appl 1996; 675: 157-161.
16. Zhen Q, Xu B, Ma L, Tian G, Tang X, Ding M. Simultaneous determination of tryptophan, kynurenine and 5-hydroxytryptamine by HPLC: application in uremic patients undergoing hemodialysis. Clin Biochem 2011; 44: 226-230.
17. Vignau J, Jacquemont M-C, Lefort A, Imbenotte M, Lhermitte M. Simultaneous determination of tryptophan and kynurenine in serum by HPLC with UV and fluorescence detection. Biomed Chromatogr 2004; 18: 872-874.
18. Huether G, Hajak G, Reimer A, et al. The metabolic fate of infused L-tryptophan in men: possible clinical implications of the accumulation of circulating tryptophan and tryptophan metabolites. Psychopharmacology 1992; 109: 422-423.
19. Wood AT, Hall MR. Reversed-phase high-performance liquid chromatography of catecholamines and indoleamines using a simple gradient solvent system and native fluorescence detection. J Chromatogr B Biomed Sci Appl 2000; 744: 221-225.
20. Rosanna M, Chau W, Bhavik AP. Determination of serotonin, melatonin and metabolites in gastrointestinal tissue using highperformance liquid chromatography with electrochemical detection. Biomed Chromatogr 2009; 23: 175-181.
21. Vaarmann A, Kask A, Maeorg U. Novel and sensitive highperformance liquid chromatographic method based on electrochemical coulometric array detection for simultaneous determination of catecholamines, kynurenine and indole derivates of tryptophan. J Chromatogr B Analyt Technol Biomed Life Sci 2002; 769: 145-153.
22. de Jong WH, Smit R, Bakker SJ, de Vries EG, Kema IK. Plasma tryptophan, kynurenine and 3-hydroxsykynurenine measurement using automated on-line solid-phase extraction HPLC-tandem mass spectrometry. J Chromatog B Analyt Technol Biomed Life Sci 2009; 877: 603-609.
23. Slominski A, Semak I, Pisarchik A, et al. Conversion of Ltryptophan to serotonin and melatonin in human melanoma cells. FEBS Lett 2002; 511: 102-106.
24. Widner B, Werner ER, Schennach H, Wachter H, Fuchs D. Simultaneous measurement of serum tryptophan and tynurenine by HPLC. Clin Chem 1997; 43: 242-2426.
25. Polson C, Sarkar P, Incledon B, Raguvaran V, Grant R. Optimization of protein precipitation based upon effectiveness of protein removal and ionization in liquid chromatography-tandem mass spectrometry. J Chromatog B Analyt Technol Biomed Life Sci 2003; 785: 263-275.
26. Peniston-Bird JF, Di WL, Street CA, Kadva A, Stalteri MA, Silman RE. HPLC assay of melatonin in plasma with fluorescence detection. Clin Chem 1993; 39: 2242-2247.
27. Rizzo V, Porta C, Moroni M, Scoglio E, Moratti R. Determiation of free and total (free plus protein-bound) melatonin in plasma and cerebrospinal fluid by highperformance liqid chromatography with fluorescence detection. J Chromatog B Analyt Technol Biomed Life Sci 2002; 774: 17-24.
28. Iinuma F, Hamase K, Matsubayashi S, Takahashi M, Watanabe M, Zaitsu K. Sensitive determination of melatonin by precolumn derivatization and reversed-phase highperformance liquid chromatography. J Chromatog A 1999; 835: 67-72.
29. Yang S, Zheng X, Xu Y, Zhou X. Rapid determination of serum melatonin by ESI-MS-MS with direct sample injection. J Pharm Biomed Anal 2001; 30: 781-790.
30. Welp A, Manz B, Peschke E. Development and validation of high throughput direct radioimmunoassay for the quantitative determination of serum and plasma melatonin (N-acetyl-5-methoxytryptamine) in mice. J Immunol Methods 2010; 358: 1-8.
31. Huether G, Messner M, Rodenbeck A, Hardeland R. Effect of continuous melatonin infusion on steady-state plasma melatonin levels in rats under physiological conditions. J Pineal Res 1989; 24: 146-151.
32. Jaworek J, Leja-Szpak A, Bonior J, et al. Protective effect of melatonin and its precursor L-tryptophan on acute pancreatitis induce by caerulein overstimulation or ischemia/reperfusion. J Pineal Res. 2003; 34: 40-52.
33. Konturek SJ, Konturek PC, Brzozowska I, et al. Localization and biological; activities of melatonin in intact and diseased gastrointestinal tract (GIT). J Physiol Pharmacol 2007; 58: 381-405.
34. Bubenik GA, Pang SF, Cockshut JR, et al. Circadian variation of portent arterial and venous blood levels of melatonin in pigs and its relationship to food intake and sleep. J Pineal Res 2000; 28: 9-15.
35. Reiter RJ, Rosales-Corral S, Coto-Montes A, et al. The photoperiod, circadian regulation and chronodisruption: the requisite interplay between the suprachiasmatic nuclei and the pineal and gut melatonin. J Physiol Pharmacol 2011; 62: 269-274.
36. Celinski K, Konturek PC, Konturek SJ, et al. Effects of melatonin and tryptophan on healing of gastric and duodenal ulcers with Helicobacter pylori infection in humans. J Physiol Pharmacol 2011; 62: 521-526.