The effect of pH on horseradish peroxidase-catalyzed oxidation of melatonin: Production of N1-acetyl-N2-formyl-5- methoxykynuramine versus radical-mediated degradation

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dc.contributor.authorXimenes, Valdecir Farias [UNESP]
dc.contributor.authorFernandes, João Roberto [UNESP]
dc.contributor.authorBueno, Vânia B.
dc.contributor.authorCatalani, Luiz H.
dc.contributor.authorOliveira, Georgino H. de [UNESP]
dc.contributor.authorMachado, Rosângela G. P. [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2014-05-27T11:22:26Z
dc.date.available2014-05-27T11:22:26Z
dc.date.issued2007-04-01
dc.description.abstractThere is a growing body of evidence that melatonin and its oxidation product, N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK), have anti-inflammatory properties. From a nutritional point of view, the discovery of melatonin in plant tissues emphasizes the importance of its relationship with plant peroxidases. Here we found that the pH of the reaction mixture has a profound influence in the reaction rate and products distribution when melatonin is oxidized by the plant enzyme horseradish peroxidase. At pH 5.5, 1 mm of melatonin was almost completely oxidized within 2 min, whereas only about 3% was consumed at pH 7.4. However, the relative yield of AFMK was higher in physiological pH. Radical-mediated oxidation products, including 2-hydroxymelatonin, a dimer of 2-hydroxymelatonin and O-demethylated dimer of melatonin account for the fast consumption of melatonin at pH 5.5. The higher production of AFMK at pH 7.4 was explained by the involvement of compound III of peroxidases as evidenced by spectral studies. On the other hand, the fast oxidative degradation at pH 5.5 was explained by the classic peroxidase cycle. © 2007 The Authors.en
dc.description.affiliationDepartamento de Química Faculdade de Ciências Universidade Estadual Paulista, Bauru
dc.description.affiliationInstituto de Química Universidade de São Paulo, São Paulo
dc.description.affiliationDepartamento de Princípios Ativos e Naturais Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista, Araraquara, São Paulo
dc.description.affiliationDepartamento de Química Faculdade de Ciências de Bauru Universidade Do Estado de São Paulo, CEP 17033-360
dc.description.affiliationUnespDepartamento de Química Faculdade de Ciências Universidade Estadual Paulista, Bauru
dc.description.affiliationUnespDepartamento de Princípios Ativos e Naturais Faculdade de Ciências Farmacêuticas Universidade Estadual Paulista, Araraquara, São Paulo
dc.format.extent291-296
dc.identifierhttp://dx.doi.org/10.1111/j.1600-079X.2007.00419.x
dc.identifier.citationJournal of Pineal Research, v. 42, n. 3, p. 291-296, 2007.
dc.identifier.doi10.1111/j.1600-079X.2007.00419.x
dc.identifier.issn0742-3098
dc.identifier.issn1600-079X
dc.identifier.lattes4066413997908572
dc.identifier.lattes8540599256820672
dc.identifier.scopus2-s2.0-33847641335
dc.identifier.urihttp://hdl.handle.net/11449/69594
dc.language.isoeng
dc.relation.ispartofJournal of Pineal Research
dc.relation.ispartofjcr11.613
dc.relation.ispartofsjr3,945
dc.rights.accessRightsAcesso restrito
dc.sourceScopus
dc.subject2-hydroxymelatonin
dc.subjectHorseradish peroxidase
dc.subjectMelatonin
dc.subjectMelatonin dimer
dc.subjectN 1-acetyl-N2-formyl-5-methoxykynuramine
dc.subjecthorseradish peroxidase
dc.subjectmelatonin
dc.subjectmelatonin derivative
dc.subjectn1 acetyl n2 formyl 5 methoxykynuramine
dc.subjectunclassified drug
dc.subjectcatalysis
dc.subjectcatalyst
dc.subjectchemical reaction
dc.subjectdemethylation
dc.subjectenzyme activity
dc.subjectenzyme metabolism
dc.subjectmethylation
dc.subjectnonhuman
dc.subjectoxidation
dc.subjectpH
dc.subjectHorseradish Peroxidase
dc.subjectHydrogen-Ion Concentration
dc.subjectKynuramine
dc.subjectOxidation-Reduction
dc.titleThe effect of pH on horseradish peroxidase-catalyzed oxidation of melatonin: Production of N1-acetyl-N2-formyl-5- methoxykynuramine versus radical-mediated degradationen
dc.typeArtigo
dcterms.licensehttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
unesp.author.lattes4066413997908572
unesp.author.lattes8540599256820672
unesp.campusUniversidade Estadual Paulista (Unesp), Faculdade de Ciências Farmacêuticas, Araraquarapt
unesp.campusUniversidade Estadual Paulista (Unesp), Faculdade de Ciências, Baurupt
unesp.departmentQuímica - FCpt
unesp.departmentPrincípios Ativos Naturais e Toxicologia - FCFpt

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Bauru - FC - Faculdade de Ciências
Araraquara - FCF - Faculdade de Ciências Farmacêuticas