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Título : Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers
Autor: Batista Junior, João M.
Batista, Andrea N. L.
Rinaldo, Daniel
Vilegas, Wagner
Ambrósio, Daniela L.
Cicarelli, Regina M. B.
Bolzani, Vanderlan S.
Kato, Massuo J.
Nafie, Laurence A.
López, Silvia N.
Fulan, Maysa
Palavras-chave: Trypanocidal activity
Gaudichaudianic acid
Trypanocidal compounds
Atividade tripanocida
Ácido gaudichaudianum
Compostos tripanocidas
Publicador: The American Chemical Society and American Society of Pharmacognosy
Data da publicação: 2011
Referência: BATISTA JUNIOR, J. M. et al. Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers. Journal of Natural Products, Cincinnati, v. 74, n. 5, p. 1154–1160, 2011.
Abstract: 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 showed a synergistic effect, with the racemic mixture being the most active.
URI: http://pubs.acs.org/doi/abs/10.1021/np200085h
repositorio.ufla.br/jspui/handle/1/15362
Idioma: en_US
Aparece nas coleções:DQI - Artigos publicados em periódicos

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