Urinary metabolites and antioxidant products of exogenous melatonin in the mouse

Journal of Pineal Research

Volumn 40, Issue 4, 2006, Pages 343-349

  Ma, Xiaochao ^a   Idle, Jeffrey R ^b   Krausz, Kristopher W ^a   Tan, Dun Xian ^c   Ceraulo, Leopoldo ^d   Gonzalez, Frank J ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b CHARLES UNIVERSITY   (Czech Republic)

^c UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

^d UNIVERSITY OF PALERMO   (Italy)

Author keywords

Antioxidants; Melatonin; Mouse; Urine

Indexed keywords

3 HYDROXYMELATONIN; 6 HYDROXYMELATONIN; ANTIOXIDANT; KYNURAMINE; MELATONIN; N [2 (5 METHOXY 2 OXO 2,3 DIHYDRO 1H INDOL 3 YL)ETHYL]ACETAMIDE; N ACETYL 5 METHOXYKYNURAMINE; REACTIVE OXYGEN METABOLITE; SCAVENGER; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; GAS CHROMATOGRAPHY; HEART PROTECTION; HORMONE ACTION; IN VIVO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOUSE; NEUROPROTECTION; NONHUMAN; RING OPENING; SLEEP DISORDER; URINARY EXCRETION;

ANIMALS; CHROMATOGRAPHY, LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MALE; MELATONIN; MICE;

EID: 33645449734     PISSN: 07423098     EISSN: 1600079X     Source Type: Journal    
DOI: 10.1111/j.1600-079X.2006.00321.x     Document Type: Article

References (34)

1. S kene DJ L ockley SW A rendt J Use of melatonin in the treatment of phase shift and sleep disorders Adv Exp Med Biol 1999 467 79 84
2. S harkey KM E astman CI Melatonin phase shifts human circadian rhythms in a placebo-controlled simulated night-work study Am J Physiol Regul Integr Comp Physiol 2002 282 R454 463
3. T homas B M ohanakumar KP Melatonin protects against oxidative stress caused by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the mouse nigrostriatum J Pineal Res 2004 36 25 32
4. C hen Z C hua CC G ao J et al. Protective effect of melatonin on myocardial infarction Am J Physiol Heart Circ Physiol 2003 284 H1618 1624
5. R eiter RJ T an DX O suna C et al. Actions of melatonin in the reduction of oxidative stress. A review J Biomed Sci 2000 7 444 458
6. S ener G S ehirli AO A yanoglu -D ulger G Protective effects of melatonin, vitamin E and N-acetylcysteine against acetaminophen toxicity in mice: a comparative study J Pineal Res 2003 35 61 68
7. O geturk M K us I K avakli A et al. Effects of melatonin on carbon tetrachloride-induced changes in rat serum J Physiol Biochem 2004 60 205 210
8. J ahovic N S ener G C evik H et al. Amelioration of methotrexate-induced enteritis by melatonin in rats Cell Biochem Funct 2004 22 169 178
9. B aydas G C anatan H T urkoglu A Comparative analysis of the protective effects of melatonin and vitamin E on streptozocin-induced diabetes mellitus J Pineal Res 2002 32 225 230
10. P arlakpinar H O zer MK S ahna E et al. Amikacin-induced acute renal injury in rats: protective role of melatonin J Pineal Res 2003 35 85 90
11. S hifow AA K umar KV N aidu MU et al. Melatonin, a pineal hormone with antioxidant property, protects against gentamicin-induced nephrotoxicity in rats Nephron 2000 85 167 174
12. S ewerynek E R eiter RJ M elchiorri D et al. Oxidative damage in the liver induced by ischemia-reperfusion: protection by melatonin Hepatogastroenterology 1996 43 898 905
13. K unduzova OR E scourrou G S eguelas MH et al. Prevention of apoptotic and necrotic cell death, caspase-3 activation, and renal dysfunction by melatonin after ischemia/reperfusion FASEB J 2003 17 872 874
14. W akatsuki A O katani Y S hinohara K et al. Melatonin protects against ischemia/reperfusion-induced oxidative damage to mitochondria in fetal rat brain J Pineal Res 2001 31 167 172
15. O zdemir D T ugyan K U ysal N et al. Protective effect of melatonin against head trauma-induced hippocampal damage and spatial memory deficits in immature rats Neurosci Lett 2005 385 234 239
16. L opez PM F inana IT de A gueda MC et al. Protective effect of melatonin against oxidative stress induced by ligature of extra-hepatic biliary duct in rats: comparison with the effect of S-adenosyl-L-methionine J Pineal Res 2000 28 143 149
17. E l -S okkary GH O mar HM H assanein AF et al. Melatonin reduces oxidative damage and increases survival of mice infected with Schistosoma mansoni Free Radic Biol Med 2002 32 319 332
18. T an DX M anchester LC R eiter RJ et al. Melatonin directly scavenges hydrogen peroxide: a potentially new metabolic pathway of melatonin biotransformation Free Radic Biol Med 2000 29 1177 1185
19. R eiter RJ T an DX M anchester LC et al. Melatonin: detoxification of oxygen and nitrogen-based toxic reactants Adv Exp Med Biol 2003 527 539 548
20. H irata F H ayaishi O T okuyama T et al. In vitro and in vivo formation of two new metabolites of melatonin J Biol Chem 1974 249 1311 1313
21. H ardeland R B alzer I P oeggeler B et al. On the primary functions of melatonin in evolution: mediation of photoperiodic signals in a unicell, photooxidation, and scavenging of free radicals J Pineal Res 1995 18 104 111
22. D e A lmeida EA M artinez GR K litzke CF et al. Oxidation of melatonin by singlet molecular oxygen (O2(1deltag)) produces N1-acetyl-N2-formyl-5- methoxykynurenine J Pineal Res 2003 35 131 137
23. R ozov SV F ilatova EV O rlov AA et al. N1-acetyl-N2-formyl-5- methoxykynuramine is a product of melatonin oxidation in rats J Pineal Res 2003 35 245 250
24. A gozzino P A vellone G B ongiorno D et al. Melatonin: structural characterization of its non-enzymatic mono-oxygenate metabolite J Pineal Res 2003 35 269 275
25. T an DX M anchester LC R eiter RJ et al. A novel melatonin metabolite, cyclic 3-hydroxymelatonin: a biomarker of in vivo hydroxyl radical generation Biochem Biophys Res Commun 1998 253 614 620
26. Y oung IM L eone RM F rancis P et al. Melatonin is metabolized to N-acetyl serotonin and 6-hydroxymelatonin in man J Clin Endocrinol Metab 1985 60 114 119
27. M a X I dle JR K rausz KW et al. Metabolism of melatonin by human cytochromes P450 Drug Metab Dispos 2005 33 489 494
28. S aaf J W etterberg L B ackstrom M et al. Melatonin administration to dogs J Neural Transm 1980 49 281 285
29. K ovacs J B rodner W K irchlechner V et al. Measurement of urinary melatonin: a useful tool for monitoring serum melatonin after its oral administration J Clin Endocrinol Metab 2000 85 666 670
30. V akkuri O L eppaluoto J K auppila A Oral administration and distribution of melatonin in human serum, saliva and urine Life Sci 1985 37 489 495
31. S ilva SO R odrigues MR C arvalho SR et al. Oxidation of melatonin and its catabolites, N1-acetyl-N2 -formyl-5-methoxykynuramine and N1-acetyl-5-methoxykynuramine, by activated leukocytes J Pineal Res 2004 37 171 175
32. R essmeyer AR M ayo JC Z elosko V et al. Antioxidant properties of the melatonin metabolite N1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction Redox Rep 2003 8 205 213
33. M ayo JC S ainz RM T an DX et al. Anti-inflammatory actions of melatonin and its metabolites, N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK) and N1-acetyl-5-methoxykynuramine (AMK), in macrophages J Neuroimmunol 2005 165 139 149
34. H ardeland R P andi -P erumal SR Melatonin, a potent agent in antioxidative defense: actions as a natural food constituent, gastrointestinal factor, drug and prodrug Nutr Metab (Lond) 2005 2 22