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

Authors


Address reprint requests to Leopoldo Ceraulo, via Archirafi, 32, 90123 Palermo Italy.
E-mail: lceraulo@unipa.it

Abstract

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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