Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata

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dc.contributor.authorMannochio-Russo, Helena [UNESP]
dc.contributor.authorNunes, Wilhan D. G.
dc.contributor.authorAlmeida, Rafael F.
dc.contributor.authorAlbernaz, Lorena C.
dc.contributor.authorEspindola, Laila S.
dc.contributor.authorBolzani, Vanderlan S. [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (UNESP)
dc.contributor.institutionScience and Technology of São Paulo (IFSP)
dc.contributor.institutionUniversidade Estadual de Goiás
dc.contributor.institutionUniversidade de Brasília (UnB)
dc.date.accessioned2023-07-29T13:44:08Z
dc.date.available2023-07-29T13:44:08Z
dc.date.issued2023-03-24
dc.description.abstractThe Aedes aegypti (Diptera: Culicidae) mosquito is the vector of several arboviruses in tropical and subtropical areas of the globe, and synthetic pesticides remain the most widely used combat strategy. This study describes the investigation of secondary metabolites with larvicidal activity from the Malpighiaceae taxon using a metabolomic and bioactivity-based approach. The workflow initially consisted of a larvicidal screening of 394 extracts from the leaves of 197 Malpighiaceae samples, which were extracted using solvents of different polarity, leading to the selection of Heteropterys umbellata for the identification of active compounds. By employing untargeted mass spectrometry-based metabolomics and multivariate analyses (PCA and PLS-DA), it was possible to determine that the metabolic profiles of different plant organs and collection sites differed significantly. A bioguided approach led to the isolation of isochlorogenic acid A (1) and the nitropropanoyl glucosides karakin (2) and 1,2,3,6-tetrakis-O-[3-nitropropanoyl]-beta-glucopyranose (3). These nitro compounds exhibited larvicidal activity, possibly potentialized by synergistic effects of their isomers in chromatographic fractions. Additionally, targeted quantification of the isolated compounds in different extracts corroborated the untargeted results from the statistical analyses. These results support a metabolomic-guided approach in combination with classical phytochemical techniques to search for natural larvicidal compounds for arboviral vector control.en
dc.description.affiliationNuBBE Department of Biochemistry and Organic Chemistry Institute of Chemistry São Paulo State University (UNESP) SP, SP
dc.description.affiliationFederal Institute of Education Science and Technology of São Paulo (IFSP), SP
dc.description.affiliationUniversidade Estadual de Goiás, Herbário JAR, GO
dc.description.affiliationLaboratório de Farmacognosia Universidade de Brasília (UnB) Campus Universitário Darcy Ribeiro, Asa Norte, DF
dc.description.affiliationUnespNuBBE Department of Biochemistry and Organic Chemistry Institute of Chemistry São Paulo State University (UNESP) SP, SP
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de Goiás
dc.description.sponsorshipUniversidade de Brasília
dc.format.extent621-632
dc.identifierhttp://dx.doi.org/10.1021/acs.jnatprod.2c00788
dc.identifier.citationJournal of Natural Products, v. 86, n. 3, p. 621-632, 2023.
dc.identifier.doi10.1021/acs.jnatprod.2c00788
dc.identifier.issn1520-6025
dc.identifier.issn0163-3864
dc.identifier.scopus2-s2.0-85149130437
dc.identifier.urihttp://hdl.handle.net/11449/248439
dc.language.isoeng
dc.relation.ispartofJournal of Natural Products
dc.sourceScopus
dc.titleOld Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellataen
dc.typeArtigo
unesp.author.orcid0000-0002-4961-2353[1]
unesp.author.orcid0000-0001-7019-5825[6]

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