Biomimetic oxidation of piperine and piplartine catalyzed by iron(III) and manganese(III) porphyrins.
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.
Schaab
Estela Hanauer
EH
Universidade de São Paulo, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Av. Café s/n, Ribeirão Preto-SP 14040-903, Brazil.
Crotti
Antonio Eduardo Miller
AE
Iamamoto
Yassuko
Y
Kato
Massuo Jorge
MJ
Lotufo
Letícia Veras Costa
LV
Lopes
Norberto Peporine
NP
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
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