Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers

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dc.contributor.authorBatista, Joao M. [UNESP]
dc.contributor.authorBatista, Andrea N. L. [UNESP]
dc.contributor.authorRinaldo, Daniel [UNESP]
dc.contributor.authorVilegas, Wagner [UNESP]
dc.contributor.authorAmbrosio, Daniela L. [UNESP]
dc.contributor.authorCicarelli, Regina Maria Barreto [UNESP]
dc.contributor.authorBolzani, Vanderlan da Silva [UNESP]
dc.contributor.authorKato, Massuo J.
dc.contributor.authorNafie, Laurence A.
dc.contributor.authorLopez, Silvia N.
dc.contributor.authorFurlan, Maysa [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.contributor.institutionSyracuse Univ
dc.contributor.institutionUniv Nacl Rosario
dc.date.accessioned2014-05-20T14:20:50Z
dc.date.available2014-05-20T14:20:50Z
dc.date.issued2011-05-01
dc.description.abstractGaudichaudianic 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.en
dc.description.affiliationUniv Estadual Paulista UNESP, Inst Quim, Dept Quim Organ, BR-14800900 Araraquara, SP, Brazil
dc.description.affiliationUniv Estadual Paulista UNESP, Fac Ciencias Farmaceut, BR-14801902 Araraquara, SP, Brazil
dc.description.affiliationUniv São Paulo USP, Inst Quim, BR-05508900 São Paulo, Brazil
dc.description.affiliationSyracuse Univ, Dept Chem, Syracuse, NY 13244 USA
dc.description.affiliationUniv Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, RA-2000 Rosario, Santa Fe, Argentina
dc.description.affiliationUnespUniv Estadual Paulista UNESP, Inst Quim, Dept Quim Organ, BR-14800900 Araraquara, SP, Brazil
dc.description.affiliationUnespUniv Estadual Paulista UNESP, Fac Ciencias Farmaceut, BR-14801902 Araraquara, SP, Brazil
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipIdFAPESP: 03/02176-7
dc.description.sponsorshipIdFAPESP: 08/58658-3
dc.description.sponsorshipIdCAPES: 3686/09-4
dc.format.extent1154-1160
dc.identifierhttp://dx.doi.org/10.1021/np200085h
dc.identifier.citationJournal of Natural Products. Washington: Amer Chemical Soc, v. 74, n. 5, p. 1154-1160, 2011.
dc.identifier.doi10.1021/np200085h
dc.identifier.issn0163-3864
dc.identifier.lattes4484083685251673
dc.identifier.lattes1308042794786872
dc.identifier.orcid0000-0003-3032-2556
dc.identifier.urihttp://hdl.handle.net/11449/26254
dc.identifier.wosWOS:000291127900036
dc.language.isoeng
dc.publisherAmer Chemical Soc
dc.relation.ispartofJournal of Natural Products
dc.relation.ispartofjcr3.885
dc.relation.ispartofsjr1,368
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.titleAbsolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomersen
dc.typeArtigo
dcterms.licensehttp://pubs.acs.org/page/policy/nih/index.html
dcterms.rightsHolderAmer Chemical Soc
unesp.author.lattes4484083685251673
unesp.author.lattes1308042794786872
unesp.author.orcid0000-0001-5363-6481[3]
unesp.author.orcid0000-0003-3032-2556[4]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Química, Araraquarapt

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