title: Melatonin: structural characterization of its non-enzymatic mono-oxygenate metabolite.
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.
authors.affiliation: Dipartimento di Chimica e Tecnologie Farmaceutiche, Via Archirafi, Palermo, Italy.
authors.forename: Pasquale
authors.initials: P
authors.lastname: Agozzino
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Avellone
authors.forename: David
authors.initials: D
authors.lastname: Bongiorno
authors.forename: Leopoldo
authors.initials: L
authors.lastname: Ceraulo
authors.forename: Felice
authors.initials: F
authors.lastname: Filizzola
authors.forename: Maria C
authors.initials: MC
authors.lastname: Natoli
authors.forename: Maria A
authors.initials: MA
authors.lastname: Livrea
authors.forename: Luisa
authors.initials: L
authors.lastname: Tesoriere
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008550:Melatonin / Q000031:analogs & derivatives / Q000096:biosynthesis / Q000737:chemistry* / Q000378:metabolism*
chemical_list: C487380:N-(2-(5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl)ethyl)acetamide; D008550:Melatonin