Biosynthetic insights into p-Hydroxybenzoic acid-Derived benzopyrans in piper gaudichaudianum

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dc.contributor.authorBatista, Andrea N. L. [UNESP]
dc.contributor.authorBatista, João M.
dc.contributor.authorSouza‑Moreira, Tatiana M. [UNESP]
dc.contributor.authorValentini, Sandro R. [UNESP]
dc.contributor.authorKato, Massuo J.
dc.contributor.authorZanelli, Cleslei F. [UNESP]
dc.contributor.authorFurlan, Maysa [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade Federal de São Carlos (UFSCar)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.date.accessioned2018-12-11T17:36:22Z
dc.date.available2018-12-11T17:36:22Z
dc.date.issued2018-05-01
dc.description.abstractPiper gaudichaudianum Kunth (Piperaceae) accumulates gaudichaudianic acid, a prenylated benzopyran, as its major component. Interestingly, this trypanocidal compound occurs as a racemic mixture. Herein, transcriptomic investigations of Piper gaudichaudianum using the RNA-seq approach are reported, and from the analysis of the transcripts expressed it was possible to propose a complete biosynthetic pathway for the production of gaudichaudianic acid, including the steps that originate its precursor, p-hydroxybenzoic acid. Peperomia obtusifolia (L.) A. Dietr. (Piperaceae) also accumulates racemic benzopyrans, however, its chromanes originate from the polyketide pathway, while the chromenes from Piper derives from the shikimate pathway. Recent transcriptomic and proteomic studies of the former species did not identify polyketide synthases involved in the production of the benzopyran moiety, but revealed the expression of tocopherol cyclase, which may be responsible for the cyclization of the 3,4-dihydro-2H-pyran ring. The analysis of the enzymes involved in the secondary metabolism of Piper gaudichaudianum and the comparison with the data previously obtained from Peperomia obtusifolia can provide valuable information on how these compounds are biosynthesized.en
dc.description.affiliationInstituto de Química Universidade Estadual Paulista (UNESP)
dc.description.affiliationDepartamento de Química Universidade Federal de São Carlos (UFSCar)
dc.description.affiliationFaculdade de Ciências Farmacêuticas Universidade Estadual Paulista (UNESP)
dc.description.affiliationInstituto de Química Universidade de São Paulo (USP)
dc.description.affiliationUnespInstituto de Química Universidade Estadual Paulista (UNESP)
dc.description.affiliationUnespFaculdade de Ciências Farmacêuticas Universidade Estadual Paulista (UNESP)
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.description.sponsorshipDépartement Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipIdFAPESP: 2013/07600-3
dc.description.sponsorshipIdDépartement Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique: 2014/25222-9
dc.description.sponsorshipIdDépartement Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique: 2014/50316-7
dc.description.sponsorshipIdDépartement Caractérisation et Élaboration des Produits Issus de l’Agriculture, Institut National de la Recherche Agronomique: 2015/07089-2
dc.description.sponsorshipIdFAPESP: 2011/01003-8
dc.format.extent1105-1114
dc.identifierhttp://dx.doi.org/10.21577/0103-5053.20170238
dc.identifier.citationJournal of the Brazilian Chemical Society, v. 29, n. 5, p. 1105-1114, 2018.
dc.identifier.doi10.21577/0103-5053.20170238
dc.identifier.fileS0103-50532018000501105.pdf
dc.identifier.issn1678-4790
dc.identifier.issn0103-5053
dc.identifier.lattes1308042794786872
dc.identifier.lattes1525665408900195
dc.identifier.orcid0000-0001-7831-1149
dc.identifier.scieloS0103-50532018000501105
dc.identifier.scopus2-s2.0-85044254973
dc.identifier.urihttp://hdl.handle.net/11449/179691
dc.language.isoeng
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.relation.ispartofsjr0,357
dc.relation.ispartofsjr0,357
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.subjectBiosynthesis
dc.subjectChromene
dc.subjectDe novo assembly
dc.subjectPiperaceae
dc.subjectRNA-seq
dc.subjectTranscriptome
dc.titleBiosynthetic insights into p-Hydroxybenzoic acid-Derived benzopyrans in piper gaudichaudianumen
dc.typeArtigo
unesp.author.lattes1308042794786872
unesp.author.lattes1525665408900195[6]
unesp.author.orcid0000-0001-7831-1149[6]

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