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

• Published in: Biological & Pharmaceutical Bulletin Vol. 33; no. 5; pp. 912 - 916
• Main Authors: Schaab, Estela Hanauer, Crotti, Antonio Eduardo Miller, Iamamoto, Yassuko, Kato, Massuo Jorge, Lotufo, Letícia Veras Costa, Lopes, Norberto Peporine
• Format: Journal Article
• Language: English; Japanese
• Published: Japan The Pharmaceutical Society of Japan 2010; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: Alkaloids - metabolism; Benzodioxoles - metabolism; Biological Products; biomimetic oxidation; Biomimetics; Catalysis; Cytochrome P-450 Enzyme System - chemistry; Ferric Compounds - chemistry; Inactivation, Metabolic; Iodobenzenes - metabolism; Iron - chemistry; Manganese - chemistry; mass spectrometry; metalloporphyrin; Oxidation-Reduction; Piperidines - metabolism; Piperidones - metabolism; piperine; piplartine; Polyunsaturated Alkamides - metabolism; Porphyrins - chemical synthesis; Porphyrins - chemistry; Singlet Oxygen; Spectrometry, Mass, Electrospray Ionization
• ISSN: 0918-6158; 1347-5215
• DOI: 10.1248/bpb.33.912

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.