Biomimetic Oxidation of Piperine and Piplartine Catalyzed by Iron(III) and Manganese(III) Porphyrins

Estela Hanauer Schaab; Antonio Eduardo Miller Crotti; Yassuko Iamamoto; Massuo Jorge Kato; Letícia Veras Costa Lotufo; Norberto Peporine Lopes

doi:10.1248/bpb.33.912

Note

Biomimetic Oxidation of Piperine and Piplartine Catalyzed by Iron(III) and Manganese(III) Porphyrins

Estela Hanauer Schaab, Antonio Eduardo Miller Crotti, Yassuko Iamamoto, Massuo Jorge Kato, Letícia Veras Costa Lotufo, Norberto Peporine Lopes

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Keywords: piperine, piplartine, metalloporphyrin, biomimetic oxidation, mass spectrometry

JOURNAL FREE ACCESS

2010 Volume 33 Issue 5 Pages 912-916

DOI https://doi.org/10.1248/bpb.33.912

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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.

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