UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.jchromb.2019.04.029 http://hdl.handle.net/11449/189058 |
Resumo: | The classical approach to drug discovery from natural products (NP's) requires strenuous and complex purification steps for the isolation and structural elucidation. Modern strategies as dereplication aim to accelerate the identification of known compounds present in a crude or partially purified extract. In this work, we investigated the influence of the solid-phase extraction (Oasis, Plexa, and Agilent C18 cartridges with and without organic modifiers) chemical profile obtained by UPLC-QTOF-MS and NMR and cytotoxicities of aqueous extracts from Phyllanthus niruri and P. amarus. Our results showed differences between the SPE cartridges and the mass recovered. P. niruri showed higher mass recovery than P. amarus indicating a higher amount of secondary metabolites. The UPLC-QTOF-MS analysis revealed that P. niruri crude extract presents higher contents of phenolic compounds than P. amarus. According to NMR analysis, P. niruri contained more tyrosine, corilagin, and glycosidic residues while P. amarus, presented higher content of ellagic acid. The different stationary phases, as well as mobile phases for exploratory SPE, enabled the exploitation of the different chemical functionalities within the Phyllanthus species. The SPE (MeOH:H 2 O 70:30 with C18 cartridges) samples showed greater in vitro cytotoxicity than the crude extracts, with IC 50 ranging from 8.01 to 94.92 μg mL −1 against the tumor lines tested. The solid phase extraction allowed the concentration of molecules with desirable physicochemical characteristics, which might increase the hit of therapeutically useful substances. |
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UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolitesCancerCytotoxicityDereplicationPhyllanthus spp.“Stone break”The classical approach to drug discovery from natural products (NP's) requires strenuous and complex purification steps for the isolation and structural elucidation. Modern strategies as dereplication aim to accelerate the identification of known compounds present in a crude or partially purified extract. In this work, we investigated the influence of the solid-phase extraction (Oasis, Plexa, and Agilent C18 cartridges with and without organic modifiers) chemical profile obtained by UPLC-QTOF-MS and NMR and cytotoxicities of aqueous extracts from Phyllanthus niruri and P. amarus. Our results showed differences between the SPE cartridges and the mass recovered. P. niruri showed higher mass recovery than P. amarus indicating a higher amount of secondary metabolites. The UPLC-QTOF-MS analysis revealed that P. niruri crude extract presents higher contents of phenolic compounds than P. amarus. According to NMR analysis, P. niruri contained more tyrosine, corilagin, and glycosidic residues while P. amarus, presented higher content of ellagic acid. The different stationary phases, as well as mobile phases for exploratory SPE, enabled the exploitation of the different chemical functionalities within the Phyllanthus species. The SPE (MeOH:H 2 O 70:30 with C18 cartridges) samples showed greater in vitro cytotoxicity than the crude extracts, with IC 50 ranging from 8.01 to 94.92 μg mL −1 against the tumor lines tested. The solid phase extraction allowed the concentration of molecules with desirable physicochemical characteristics, which might increase the hit of therapeutically useful substances.Empresa Brasileira de Pesquisa AgropecuáriaConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Federal University of Ceará Núcleo de Pesquisa e Desenvolvimento de Medicamentos-NPDM Rua Coronel Nunes de Mello 1000Embrapa Agroindústria Tropical, Rua Doutora Sara Mesquita, 2270 - PiciFederal University of Ceará Dept. of Analytical and Physical-Chemical Chemistry Science Center, Campus PiciSão Paulo State University (Unesp) School of Pharmaceutical Sciences Araraquara Department of Natural Principles and Toxicology, Rodovia Araraquara-Jaú, Km 01São Paulo State University (Unesp) School of Pharmaceutical Sciences Araraquara Department of Natural Principles and Toxicology, Rodovia Araraquara-Jaú, Km 01Empresa Brasileira de Pesquisa Agropecuária: 03.14.01.012.00.00CNPq: 303791/2016-0Rua Coronel Nunes de Mello 1000Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA)Science CenterUniversidade Estadual Paulista (Unesp)Silva, Maria Francilene SouzaSilva, Lorena Mara A.Quintela, Amanda Lemosdos Santos, André Gonzaga [UNESP]Silva, Francisca Aliny Nunesde Oliveira, Fátima de Cássia E.Alves Filho, Elenilson Godoyde Brito, Edy SousaCanuto, Kirley MarquesPessoa, ClaudiaZocolo, Guilherme Julião2019-10-06T16:28:26Z2019-10-06T16:28:26Z2019-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article51-61http://dx.doi.org/10.1016/j.jchromb.2019.04.029Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, v. 1120, p. 51-61.1873-376X1570-0232http://hdl.handle.net/11449/18905810.1016/j.jchromb.2019.04.0292-s2.0-85065067857Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciencesinfo:eu-repo/semantics/openAccess2024-06-24T14:52:02Zoai:repositorio.unesp.br:11449/189058Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T21:38:17.842694Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites |
title |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites |
spellingShingle |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites Silva, Maria Francilene Souza Cancer Cytotoxicity Dereplication Phyllanthus spp. “Stone break” |
title_short |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites |
title_full |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites |
title_fullStr |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites |
title_full_unstemmed |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites |
title_sort |
UPLC-HRMS and NMR applied in the evaluation of solid-phase extraction methods as a rational strategy of dereplication of Phyllanthus spp. aiming at the discovery of cytotoxic metabolites |
author |
Silva, Maria Francilene Souza |
author_facet |
Silva, Maria Francilene Souza Silva, Lorena Mara A. Quintela, Amanda Lemos dos Santos, André Gonzaga [UNESP] Silva, Francisca Aliny Nunes de Oliveira, Fátima de Cássia E. Alves Filho, Elenilson Godoy de Brito, Edy Sousa Canuto, Kirley Marques Pessoa, Claudia Zocolo, Guilherme Julião |
author_role |
author |
author2 |
Silva, Lorena Mara A. Quintela, Amanda Lemos dos Santos, André Gonzaga [UNESP] Silva, Francisca Aliny Nunes de Oliveira, Fátima de Cássia E. Alves Filho, Elenilson Godoy de Brito, Edy Sousa Canuto, Kirley Marques Pessoa, Claudia Zocolo, Guilherme Julião |
author2_role |
author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Rua Coronel Nunes de Mello 1000 Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA) Science Center Universidade Estadual Paulista (Unesp) |
dc.contributor.author.fl_str_mv |
Silva, Maria Francilene Souza Silva, Lorena Mara A. Quintela, Amanda Lemos dos Santos, André Gonzaga [UNESP] Silva, Francisca Aliny Nunes de Oliveira, Fátima de Cássia E. Alves Filho, Elenilson Godoy de Brito, Edy Sousa Canuto, Kirley Marques Pessoa, Claudia Zocolo, Guilherme Julião |
dc.subject.por.fl_str_mv |
Cancer Cytotoxicity Dereplication Phyllanthus spp. “Stone break” |
topic |
Cancer Cytotoxicity Dereplication Phyllanthus spp. “Stone break” |
description |
The classical approach to drug discovery from natural products (NP's) requires strenuous and complex purification steps for the isolation and structural elucidation. Modern strategies as dereplication aim to accelerate the identification of known compounds present in a crude or partially purified extract. In this work, we investigated the influence of the solid-phase extraction (Oasis, Plexa, and Agilent C18 cartridges with and without organic modifiers) chemical profile obtained by UPLC-QTOF-MS and NMR and cytotoxicities of aqueous extracts from Phyllanthus niruri and P. amarus. Our results showed differences between the SPE cartridges and the mass recovered. P. niruri showed higher mass recovery than P. amarus indicating a higher amount of secondary metabolites. The UPLC-QTOF-MS analysis revealed that P. niruri crude extract presents higher contents of phenolic compounds than P. amarus. According to NMR analysis, P. niruri contained more tyrosine, corilagin, and glycosidic residues while P. amarus, presented higher content of ellagic acid. The different stationary phases, as well as mobile phases for exploratory SPE, enabled the exploitation of the different chemical functionalities within the Phyllanthus species. The SPE (MeOH:H 2 O 70:30 with C18 cartridges) samples showed greater in vitro cytotoxicity than the crude extracts, with IC 50 ranging from 8.01 to 94.92 μg mL −1 against the tumor lines tested. The solid phase extraction allowed the concentration of molecules with desirable physicochemical characteristics, which might increase the hit of therapeutically useful substances. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-10-06T16:28:26Z 2019-10-06T16:28:26Z 2019-07-01 |
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/10.1016/j.jchromb.2019.04.029 Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, v. 1120, p. 51-61. 1873-376X 1570-0232 http://hdl.handle.net/11449/189058 10.1016/j.jchromb.2019.04.029 2-s2.0-85065067857 |
url |
http://dx.doi.org/10.1016/j.jchromb.2019.04.029 http://hdl.handle.net/11449/189058 |
identifier_str_mv |
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, v. 1120, p. 51-61. 1873-376X 1570-0232 10.1016/j.jchromb.2019.04.029 2-s2.0-85065067857 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
51-61 |
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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1808129343223758848 |