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. 2003 Nov;35(4):269-75.
doi: 10.1034/j.1600-079x.2003.00086.x.

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

Pasquale Agozzino  1 , Giuseppe Avellone, David Bongiorno, Leopoldo Ceraulo, Felice Filizzola, Maria C Natoli, Maria A Livrea, Luisa Tesoriere
Affiliations

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

Pasquale Agozzino et al. J Pineal Res. 2003 Nov.

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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