Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1021/acs.jnatprod.2c00788 http://hdl.handle.net/11449/248439 |
Resumo: | The 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. |
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Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellataThe 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.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de GoiásUniversidade de BrasíliaNuBBE Department of Biochemistry and Organic Chemistry Institute of Chemistry São Paulo State University (UNESP) SP, SPFederal Institute of Education Science and Technology of São Paulo (IFSP), SPUniversidade Estadual de Goiás, Herbário JAR, GOLaboratório de Farmacognosia Universidade de Brasília (UnB) Campus Universitário Darcy Ribeiro, Asa Norte, DFNuBBE Department of Biochemistry and Organic Chemistry Institute of Chemistry São Paulo State University (UNESP) SP, SPUniversidade Estadual Paulista (UNESP)Science and Technology of São Paulo (IFSP)Universidade Estadual de GoiásUniversidade de Brasília (UnB)Mannochio-Russo, Helena [UNESP]Nunes, Wilhan D. G.Almeida, Rafael F.Albernaz, Lorena C.Espindola, Laila S.Bolzani, Vanderlan S. [UNESP]2023-07-29T13:44:08Z2023-07-29T13:44:08Z2023-03-24info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article621-632http://dx.doi.org/10.1021/acs.jnatprod.2c00788Journal of Natural Products, v. 86, n. 3, p. 621-632, 2023.1520-60250163-3864http://hdl.handle.net/11449/24843910.1021/acs.jnatprod.2c007882-s2.0-85149130437Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Natural Productsinfo:eu-repo/semantics/openAccess2023-07-29T13:44:08Zoai:repositorio.unesp.br:11449/248439Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-07-29T13:44:08Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata |
title |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata |
spellingShingle |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata Mannochio-Russo, Helena [UNESP] |
title_short |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata |
title_full |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata |
title_fullStr |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata |
title_full_unstemmed |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata |
title_sort |
Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata |
author |
Mannochio-Russo, Helena [UNESP] |
author_facet |
Mannochio-Russo, Helena [UNESP] Nunes, Wilhan D. G. Almeida, Rafael F. Albernaz, Lorena C. Espindola, Laila S. Bolzani, Vanderlan S. [UNESP] |
author_role |
author |
author2 |
Nunes, Wilhan D. G. Almeida, Rafael F. Albernaz, Lorena C. Espindola, Laila S. Bolzani, Vanderlan S. [UNESP] |
author2_role |
author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (UNESP) Science and Technology of São Paulo (IFSP) Universidade Estadual de Goiás Universidade de Brasília (UnB) |
dc.contributor.author.fl_str_mv |
Mannochio-Russo, Helena [UNESP] Nunes, Wilhan D. G. Almeida, Rafael F. Albernaz, Lorena C. Espindola, Laila S. Bolzani, Vanderlan S. [UNESP] |
description |
The 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. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-07-29T13:44:08Z 2023-07-29T13:44:08Z 2023-03-24 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1021/acs.jnatprod.2c00788 Journal of Natural Products, v. 86, n. 3, p. 621-632, 2023. 1520-6025 0163-3864 http://hdl.handle.net/11449/248439 10.1021/acs.jnatprod.2c00788 2-s2.0-85149130437 |
url |
http://dx.doi.org/10.1021/acs.jnatprod.2c00788 http://hdl.handle.net/11449/248439 |
identifier_str_mv |
Journal of Natural Products, v. 86, n. 3, p. 621-632, 2023. 1520-6025 0163-3864 10.1021/acs.jnatprod.2c00788 2-s2.0-85149130437 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Natural Products |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
621-632 |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
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1799965334534356992 |