title: Biomimetic oxidation of piperine and piplartine catalyzed by iron(III) and manganese(III) porphyrins.
abstract: Synthetic metalloporphyrins, in the presence of monooxygen donors, are known to mimetize various reactions of cytochrome P450 enzymes systems in the oxidation of drugs and natural products. The oxidation of piperine and piplartine by iodosylbenzene using iron(III) and manganese(III) porphyrins yielded mono- and dihydroxylated products, respectively. Piplartine showed to be a more reactive substrate towards the catalysts tested. The structures of the oxidation products were proposed based on electrospray ionization tandem mass spectrometry.
authors.affiliation: Universidade de São Paulo, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Av. Café s/n, Ribeirão Preto-SP 14040-903, Brazil.
authors.forename: Estela Hanauer
authors.initials: EH
authors.lastname: Schaab
authors.forename: Antonio Eduardo Miller
authors.initials: AE
authors.lastname: Crotti
authors.forename: Yassuko
authors.initials: Y
authors.lastname: Iamamoto
authors.forename: Massuo Jorge
authors.initials: MJ
authors.lastname: Kato
authors.forename: Letícia Veras Costa
authors.initials: LV
authors.lastname: Lotufo
authors.forename: Norberto Peporine
authors.initials: NP
authors.lastname: Lopes
mesh_terms: D000470:Alkaloids / Q000378:metabolism*; D052117:Benzodioxoles / Q000378:metabolism*; D001688:Biological Products; D032701:Biomimetics; D002384:Catalysis; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry; D005290:Ferric Compounds / Q000737:chemistry*; D008658:Inactivation, Metabolic; D007462:Iodobenzenes / Q000378:metabolism; D007501:Iron / Q000737:chemistry*; D008345:Manganese / Q000737:chemistry*; D010084:Oxidation-Reduction; D010880:Piperidines / Q000378:metabolism*; D010881:Piperidones / Q000378:metabolism*; D053284:Polyunsaturated Alkamides / Q000378:metabolism*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D026082:Singlet Oxygen; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000470:Alkaloids; D052117:Benzodioxoles; D001688:Biological Products; D005290:Ferric Compounds; D007462:Iodobenzenes; D010880:Piperidines; D010881:Piperidones; D053284:Polyunsaturated Alkamides; D011166:Porphyrins; C498077:piperlongumine; D026082:Singlet Oxygen; D008345:Manganese; D003577:Cytochrome P-450 Enzyme System; D007501:Iron; C037276:iodosobenzene; C008922:piperine