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