Melatonin: structural characterization of its non-enzymatic mono-oxygenate metabolite

: Oxidation of melatonin by Fenton reagents as well as with hypochlorous acid or oxoferryl hemoglobin has been investigated. Analysis of products by low resolution/mass spectra (MS), high resolution/MS, 1H‐nuclear magnetic resonance (NMR), 13C‐NMR, correlated spectroscopy (COSY) and heterocorrelated...

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Veröffentlicht in:	Journal of pineal research 2003-11, Vol.35 (4), p.269-275
Hauptverfasser:	Agozzino, Pasquale, Avellone, Giuseppe, Bongiorno, David, Ceraulo, Leopoldo, Filizzola, Felice, Natoli, Maria C., Livrea, Maria A., Tesoriere, Luisa
Format:	Artikel
Sprache:	eng
Schlagworte:	1D and 2D nuclear magnetic resonance Biological and medical sciences Fundamental and applied biological sciences. Psychology Hormones and neuropeptides. Regulation Hypothalamus. Hypophysis. Epiphysis. Urophysis Magnetic Resonance Spectroscopy mass spectra Mass Spectrometry melatonin Melatonin - analogs & derivatives Melatonin - biosynthesis Melatonin - chemistry Melatonin - metabolism metabolites structure Vertebrates: endocrinology
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Zusammenfassung:	: Oxidation of melatonin by Fenton reagents as well as with hypochlorous acid or oxoferryl hemoglobin has been investigated. Analysis of products by low resolution/mass spectra (MS), high resolution/MS, 1H‐nuclear magnetic resonance (NMR), 13C‐NMR, correlated spectroscopy (COSY) and heterocorrelated spectroscopy (HETCOR) 2D NMR reveals the formation of a single mono‐oxygenated product under all conditions and unequivocally assigns the N‐[2‐(5‐methoxy‐2‐oxo‐2,3‐dihydro‐1H‐indol‐3‐yl)‐ethyl]‐acetamide structure, which had not been previously considered.
ISSN:	0742-3098 1600-079X
DOI:	10.1034/j.1600-079X.2003.00086.x