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.
Agozzino, P., Avellone, G., Bongiorno, D., Ceraulo, L., Filizzola, F., Natoli, M., et al. (2003). Melatonin: Structural characterization of its non-enzymatic mono-oxygenate metabolite. JOURNAL OF PINEAL RESEARCH, 35(4), 269-275 [10.1034/j.1600-079X.2003.00086.x].
Melatonin: Structural characterization of its non-enzymatic mono-oxygenate metabolite
AGOZZINO, Pasquale;AVELLONE, Giuseppe;BONGIORNO, David;CERAULO, Leopoldo;FILIZZOLA, Felice;NATOLI, Maria Concetta;LIVREA, Maria Antonia;TESORIERE, Luisa
2003-01-01
Abstract
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.
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