Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts

Detalhes bibliográficos
Autor(a) principal: Scupinari, Tamires
Data de Publicação: 2020
Outros Autores: Mannochio Russo, Helena, Sabino Ferrari, Anna Beatriz, da Silva Bolzani, Vanderlan [UNESP], Dias, Waldir Pereira, de Oliveira Nunes, Estela, Hoffmann-Campo, Clara Beatriz, Zeraik, Maria Luiza
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1002/pca.2938
http://hdl.handle.net/11449/200518
Resumo: Introduction: Crotalaria spectabilis is an important species used as a pre-plant cover for soybean crops to control the proliferation of endoparasitic nematodes. Species from the Crotalaria genus are known for presenting pyrrolizidine alkaloids (PAs) in their composition, however, C. spectabilis is still considered chemically under-explored. Objective: The goal of this manuscript is the development and validation of a method for PAs and flavonoids identification and quantification of C. spectabilis seeds and leaves, a toxic plant used for nematode proliferation control in soil, especially in soybean crops. Materials and methods: Seeds and leaves extracts were analysed by high-performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS) for the identification of the compounds. Results: PAs and phenolic compounds could be identified in both samples based on the MS/MS fragmentation pattern. Molecular formulas of the annotated compounds were confirmed by ultra-high-performace liquid chromatography-quadrupole time-of-flight (UHPLC-QToF), and monocrotaline could also be confirmed by standard comparison. The quantification of monocrotaline was performed by HPLC-MS/MS, resulting in 123 times higher monocrotaline content in seeds than in the leaves, which could explain its efficiency in combating nematode proliferation in soil. Conclusion: This was the first report of phenolic compounds in C. spectabilis. The current study highlights the importance of C. spectabilis for nematode control due to the presence of toxic PAs, and the employment of analytical techniques for identification and quantification of compounds present in the extracts.
id UNSP_2f77f447cf70c59f7944293fd19fc040
oai_identifier_str oai:repositorio.unesp.br:11449/200518
network_acronym_str UNSP
network_name_str Repositório Institucional da UNESP
repository_id_str 2946
spelling Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extractsCrotalaria spectabilisnematode controlpyrrolizidine alkaloidstoxic plantIntroduction: Crotalaria spectabilis is an important species used as a pre-plant cover for soybean crops to control the proliferation of endoparasitic nematodes. Species from the Crotalaria genus are known for presenting pyrrolizidine alkaloids (PAs) in their composition, however, C. spectabilis is still considered chemically under-explored. Objective: The goal of this manuscript is the development and validation of a method for PAs and flavonoids identification and quantification of C. spectabilis seeds and leaves, a toxic plant used for nematode proliferation control in soil, especially in soybean crops. Materials and methods: Seeds and leaves extracts were analysed by high-performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS) for the identification of the compounds. Results: PAs and phenolic compounds could be identified in both samples based on the MS/MS fragmentation pattern. Molecular formulas of the annotated compounds were confirmed by ultra-high-performace liquid chromatography-quadrupole time-of-flight (UHPLC-QToF), and monocrotaline could also be confirmed by standard comparison. The quantification of monocrotaline was performed by HPLC-MS/MS, resulting in 123 times higher monocrotaline content in seeds than in the leaves, which could explain its efficiency in combating nematode proliferation in soil. Conclusion: This was the first report of phenolic compounds in C. spectabilis. The current study highlights the importance of C. spectabilis for nematode control due to the presence of toxic PAs, and the employment of analytical techniques for identification and quantification of compounds present in the extracts.Laboratory of Phytochemistry and Biomolecules (LabFitoBio) Department of Chemistry State University of Londrina (UEL)Nuclei of Bioassays Biosynthesis and Ecophysiology of Natural Products (NuBBE) Department of Organic Chemistry Institute of Chemistry São Paulo State University (UNESP)Brazilian Agricultural Research Corporation – Embrapa SoybeanNuclei of Bioassays Biosynthesis and Ecophysiology of Natural Products (NuBBE) Department of Organic Chemistry Institute of Chemistry São Paulo State University (UNESP)Universidade Estadual de Londrina (UEL)Universidade Estadual Paulista (Unesp)Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA)Scupinari, TamiresMannochio Russo, HelenaSabino Ferrari, Anna Beatrizda Silva Bolzani, Vanderlan [UNESP]Dias, Waldir Pereirade Oliveira Nunes, EstelaHoffmann-Campo, Clara BeatrizZeraik, Maria Luiza2020-12-12T02:08:41Z2020-12-12T02:08:41Z2020-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1002/pca.2938Phytochemical Analysis.1099-15650958-0344http://hdl.handle.net/11449/20051810.1002/pca.29382-s2.0-85085475794Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengPhytochemical Analysisinfo:eu-repo/semantics/openAccess2021-10-23T14:33:49Zoai:repositorio.unesp.br:11449/200518Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462021-10-23T14:33:49Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
title Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
spellingShingle Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
Scupinari, Tamires
Crotalaria spectabilis
nematode control
pyrrolizidine alkaloids
toxic plant
title_short Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
title_full Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
title_fullStr Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
title_full_unstemmed Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
title_sort Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC-MS/MS dereplication and monocrotaline quantification of seed and leaf extracts
author Scupinari, Tamires
author_facet Scupinari, Tamires
Mannochio Russo, Helena
Sabino Ferrari, Anna Beatriz
da Silva Bolzani, Vanderlan [UNESP]
Dias, Waldir Pereira
de Oliveira Nunes, Estela
Hoffmann-Campo, Clara Beatriz
Zeraik, Maria Luiza
author_role author
author2 Mannochio Russo, Helena
Sabino Ferrari, Anna Beatriz
da Silva Bolzani, Vanderlan [UNESP]
Dias, Waldir Pereira
de Oliveira Nunes, Estela
Hoffmann-Campo, Clara Beatriz
Zeraik, Maria Luiza
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual de Londrina (UEL)
Universidade Estadual Paulista (Unesp)
Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA)
dc.contributor.author.fl_str_mv Scupinari, Tamires
Mannochio Russo, Helena
Sabino Ferrari, Anna Beatriz
da Silva Bolzani, Vanderlan [UNESP]
Dias, Waldir Pereira
de Oliveira Nunes, Estela
Hoffmann-Campo, Clara Beatriz
Zeraik, Maria Luiza
dc.subject.por.fl_str_mv Crotalaria spectabilis
nematode control
pyrrolizidine alkaloids
toxic plant
topic Crotalaria spectabilis
nematode control
pyrrolizidine alkaloids
toxic plant
description Introduction: Crotalaria spectabilis is an important species used as a pre-plant cover for soybean crops to control the proliferation of endoparasitic nematodes. Species from the Crotalaria genus are known for presenting pyrrolizidine alkaloids (PAs) in their composition, however, C. spectabilis is still considered chemically under-explored. Objective: The goal of this manuscript is the development and validation of a method for PAs and flavonoids identification and quantification of C. spectabilis seeds and leaves, a toxic plant used for nematode proliferation control in soil, especially in soybean crops. Materials and methods: Seeds and leaves extracts were analysed by high-performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS) for the identification of the compounds. Results: PAs and phenolic compounds could be identified in both samples based on the MS/MS fragmentation pattern. Molecular formulas of the annotated compounds were confirmed by ultra-high-performace liquid chromatography-quadrupole time-of-flight (UHPLC-QToF), and monocrotaline could also be confirmed by standard comparison. The quantification of monocrotaline was performed by HPLC-MS/MS, resulting in 123 times higher monocrotaline content in seeds than in the leaves, which could explain its efficiency in combating nematode proliferation in soil. Conclusion: This was the first report of phenolic compounds in C. spectabilis. The current study highlights the importance of C. spectabilis for nematode control due to the presence of toxic PAs, and the employment of analytical techniques for identification and quantification of compounds present in the extracts.
publishDate 2020
dc.date.none.fl_str_mv 2020-12-12T02:08:41Z
2020-12-12T02:08:41Z
2020-01-01
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/10.1002/pca.2938
Phytochemical Analysis.
1099-1565
0958-0344
http://hdl.handle.net/11449/200518
10.1002/pca.2938
2-s2.0-85085475794
url http://dx.doi.org/10.1002/pca.2938
http://hdl.handle.net/11449/200518
identifier_str_mv Phytochemical Analysis.
1099-1565
0958-0344
10.1002/pca.2938
2-s2.0-85085475794
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Phytochemical Analysis
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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
_version_ 1799965740062736384