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Planta Medica Letters 2015; 2(01): e61-e64
DOI: 10.1055/s-0035-1558206
Letter
Georg Thieme Verlag KG Stuttgart · New York

Formation of a Predominant Metabolite of Hydroxydihydrocarvone Evaluated by a Biomimetic Oxidative Model and in Rat Liver Microsomes

Sara M. Thomazzi
1   Departamento de Fisiologia, Universidade Federal de Sergipe, São Cristóvão, SE, Brazil
,
Fernanda L. Moreira
2   Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil
,
Izabel C. C. Turatti
3   NPPNS, Departamento de Físico-Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil
,
Juliana N. Paula e Souza
3   NPPNS, Departamento de Físico-Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil
,
Luciana N. Andrade
1   Departamento de Fisiologia, Universidade Federal de Sergipe, São Cristóvão, SE, Brazil
,
Denise B. Silva
3   NPPNS, Departamento de Físico-Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil
,
Anderson R. M. Oliveira
4   Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil
,
Damião P. De Sousa
5   Centro de Ciências da Saúde-Campus I, Universidade Federal da Paraíba, João Pessoa, PB, Brazil
,
Norberto P. Lopes
3   NPPNS, Departamento de Físico-Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil
› Author Affiliations
Further Information

Publication History

received 16 May 2015
revised 08 July 2015

accepted 26 September 2015

Publication Date:
17 November 2015 (online)

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Abstract

This paper reports the biomimetic oxidation of hydroxydihydrocarvone by iodosylbenzene using tetraphenyl-porphine iron(III) chloride as the catalyst in ethyl acetate. Mass spectrometry fragmentation maps of hydroxydihydrocarvone (obtained by gas chromatography-mass spectrometry analyses) allowed for the identification of the major product as 4-hydroxy-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one (4-hydroxy-hydroxydihydrocarvone). This compound was also observed in an in vitro metabolism assay that employed isolated rat liver microsomes, thereby validating the biomimetic procedure.

Key words

biomimetic oxidation - drug metabolism - hydroxydihydrocarvone - liver microsomal metabolism - oxidative metabolism - phase I metabolism

Supporting Information

 

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