Literature DB >> 14521633

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

Pasquale Agozzino1, Giuseppe Avellone, David Bongiorno, Leopoldo Ceraulo, Felice Filizzola, Maria C Natoli, Maria A Livrea, Luisa Tesoriere.   

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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Year:  2003        PMID: 14521633     DOI: 10.1034/j.1600-079x.2003.00086.x

Source DB:  PubMed          Journal:  J Pineal Res        ISSN: 0742-3098            Impact factor:   13.007


  7 in total

1.  Urinary metabolites and antioxidant products of exogenous melatonin in the mouse.

Authors:  Xiaochao Ma; Jeffrey R Idle; Kristopher W Krausz; Dun-Xian Tan; Leopoldo Ceraulo; Frank J Gonzalez
Journal:  J Pineal Res       Date:  2006-05       Impact factor: 13.007

Review 2.  Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance.

Authors:  Rüdiger Hardeland
Journal:  Endocrine       Date:  2005-07       Impact factor: 3.633

3.  Metabolism of melatonin by cytochrome P450s in rat liver mitochondria and microsomes.

Authors:  Igor Semak; Elena Korik; Maria Antonova; Jacobo Wortsman; Andrzej Slominski
Journal:  J Pineal Res       Date:  2008-08-19       Impact factor: 13.007

4.  A metabolomic perspective of melatonin metabolism in the mouse.

Authors:  Xiaochao Ma; Chi Chen; Kristopher W Krausz; Jeffrey R Idle; Frank J Gonzalez
Journal:  Endocrinology       Date:  2008-01-10       Impact factor: 4.736

5.  Melatonin metabolism in the central nervous system.

Authors:  Rüdiger Hardeland
Journal:  Curr Neuropharmacol       Date:  2010-09       Impact factor: 7.363

6.  Melatonin, a potent agent in antioxidative defense: actions as a natural food constituent, gastrointestinal factor, drug and prodrug.

Authors:  Rüdiger Hardeland; S R Pandi-Perumal
Journal:  Nutr Metab (Lond)       Date:  2005-09-10       Impact factor: 4.169

Review 7.  Melatonin: A Versatile Protector against Oxidative DNA Damage.

Authors:  Annia Galano; Dun-Xian Tan; Russel J Reiter
Journal:  Molecules       Date:  2018-02-27       Impact factor: 4.411

  7 in total

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