Absolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers

dc.creatorBatista Junior, João M.
dc.creatorBatista, Andrea N. L.
dc.creatorRinaldo, Daniel
dc.creatorVilegas, Wagner
dc.creatorAmbrósio, Daniela L.
dc.creatorCicarelli, Regina M. B.
dc.creatorBolzani, Vanderlan S.
dc.creatorKato, Massuo J.
dc.creatorNafie, Laurence A.
dc.creatorLópez, Silvia N.
dc.creatorFulan, Maysa
dc.date2017-09-11T13:00:47Z
dc.date2017-09-11T13:00:47Z
dc.date2011
dc.date.accessioned2023-09-28T20:04:24Z
dc.date.available2023-09-28T20:04:24Z
dc.identifierBATISTA 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.
dc.identifierhttp://pubs.acs.org/doi/abs/10.1021/np200085h
dc.identifierrepositorio.ufla.br/jspui/handle/1/15362
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/9043769
dc.descriptionGaudichaudianic 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.
dc.languageen_US
dc.publisherThe American Chemical Society and American Society of Pharmacognosy
dc.rightsrestrictAccess
dc.sourceJournal of Natural Products
dc.subjectTrypanocidal activity
dc.subjectGaudichaudianic acid
dc.subjectTrypanocidal compounds
dc.subjectAtividade tripanocida
dc.subjectÁcido gaudichaudianum
dc.subjectCompostos tripanocidas
dc.titleAbsolute configuration and selective trypanocidal activity of gaudichaudianic acid enantiomers
dc.typeArtigo


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