Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers

Nenhuma Miniatura disponível

Data

2011-05-01

Orientador

Coorientador

Pós-graduação

Curso de graduação

Título da Revista

ISSN da Revista

Título de Volume

Editor

Amer Chemical Soc

Tipo

Artigo

Direito de acesso

Acesso restrito

Resumo

Gaudichaudianic acid, a prenylated chromene isolated from Piper gaudichaudianum, has been described as a potent trypanocidal compound against the Y-strain of Trypanosoma cruzi. We herein describe its isolation as a racemic mixture followed by enantiomeric resolution using chiral HPLC and determination of the absolute configuration of the enantiomers as (+)-S and (-)-R by means of a combination of electronic and vibrational circular dichroism using density functional theory calculations. Investigation of the EtOAc extract of the roots, stems, and leaves from both adult specimens and seedlings of P. gaudichaudianum revealed that gaudichaudianic acid is biosynthesized as a racemic mixture from the seedling stage onward. Moreover, gaudichaudianic acid was found exclusively in the roots of seedlings, while it is present in all organs of the adult plant. Trypanocidal assays indicated that the (+)-enantiomer was more active than its antipode. Interestingly, mixtures of enantiomers stowed a synergistic effect, with the racemic mixture being the most active.

Descrição

Palavras-chave

Idioma

Inglês

Como citar

Journal of Natural Products. Washington: Amer Chemical Soc, v. 74, n. 5, p. 1154-1160, 2011.

Itens relacionados