Investigação fitoquímica de espécies do gênero Erythroxylum
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFPB |
Texto Completo: | https://repositorio.ufpb.br/jspui/handle/123456789/29344 |
Resumo: | Several secondary metabolites of different classes can be evidenced in species of the genus Erythroxylum, with emphasis on flavonoids, terpenes and tropane alkaloids, the latter being considered markers of the genus. Because many of these compounds are already described in the scientific literature, modern screening and identification methodologies, such as dereplication, are necessary to direct the isolation of the metabolites of interest, representing an efficient, fast and safe strategy. This work aimed to trace the chemical profile of the secondary metabolites present in the chloroform, ethyl acetate and n-butanolic phases of the aerial parts of the species Erythroxylum simonis Plowman, Erythroxylum pauferrense Plowman, Erythroxylum pulchrum St. Hil. and Erythroxylum revolutum Mart. by dereplication methodologies. For this purpose, the phases were analyzed by high-performance liquid chromatography coupled to mass spectrometry with electrospray ionization, then the experiments were repeated with the chromatograph coupled to a high-resolution mass spectrometer, also with an electrospray ionization source, ethyl acetate and nbutanolic phases were analyzed in negative mode and chloroform phases in positive mode. The annotation of the compounds was carried out based on the ions of their deprotonated or protonated molecules, molecular formulas, fragmentation patterns and by comparing the data obtained with those present in the scientific literature. Compounds not fully annotated were isolated and characterized by 1H and 13C NMR spectroscopy. Through the analyzes carried out, it was possible to trace and compare the chemical profile of the secondary metabolites of the Erythroxylum species. The dereplication of the ethyl acetate and n-butanolic phases led to the annotation of 55 phenolic compounds, highlighting glycosylated flavonoids, phenolic acids, procyanidins, flavolignans and lignoids, most being described for the first time in the studied species, and some unpublished for the genus Erythroxylum and for the family Erythroxylaceae. The dereplication of the chloroform phases led to the annotation of 29 tropane alkaloids, some also being described for the first time in the genus and family of the studied species. From the ethyl acetate phase of E. simonis, the isolation of cinchonaines Ia and Ib, epicatechin, quercetin-O-hexoside, and biphenyl-3,3',4,4'- tetraol, described for the first time in the species, was isolated. Three compounds were isolated from the chloroform phase of E. revolutum, the protonated 6-(benzoyloxy)-3- (3,5-dimethoxy-4-hydroxybenzoyloxy)tropane, protonated 6-(benzoyloxy)-3-(3,4,5- trimethoxybenzoyloxy)tropane and protonated 6-(benzoyloxy)-3-(3,4,5- trimethoxycinnamoyloxy)tropane, reported for the first time in the species E. revolutum. This work contributed to the phytochemical knowledge of the genus Erythroxylum and demonstrates the efficiency and importance of using methodologies for guided isolation of secondary metabolites in research on natural products. |
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Investigação fitoquímica de espécies do gênero ErythroxylumErythroxylaceaeAlcaloides tropânicosCompostos fenólicosEspectroscopiaCromatografiaTropane alkaloidsPhenolic compoundsSpectroscopyChromatographyCNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIASeveral secondary metabolites of different classes can be evidenced in species of the genus Erythroxylum, with emphasis on flavonoids, terpenes and tropane alkaloids, the latter being considered markers of the genus. Because many of these compounds are already described in the scientific literature, modern screening and identification methodologies, such as dereplication, are necessary to direct the isolation of the metabolites of interest, representing an efficient, fast and safe strategy. This work aimed to trace the chemical profile of the secondary metabolites present in the chloroform, ethyl acetate and n-butanolic phases of the aerial parts of the species Erythroxylum simonis Plowman, Erythroxylum pauferrense Plowman, Erythroxylum pulchrum St. Hil. and Erythroxylum revolutum Mart. by dereplication methodologies. For this purpose, the phases were analyzed by high-performance liquid chromatography coupled to mass spectrometry with electrospray ionization, then the experiments were repeated with the chromatograph coupled to a high-resolution mass spectrometer, also with an electrospray ionization source, ethyl acetate and nbutanolic phases were analyzed in negative mode and chloroform phases in positive mode. The annotation of the compounds was carried out based on the ions of their deprotonated or protonated molecules, molecular formulas, fragmentation patterns and by comparing the data obtained with those present in the scientific literature. Compounds not fully annotated were isolated and characterized by 1H and 13C NMR spectroscopy. Through the analyzes carried out, it was possible to trace and compare the chemical profile of the secondary metabolites of the Erythroxylum species. The dereplication of the ethyl acetate and n-butanolic phases led to the annotation of 55 phenolic compounds, highlighting glycosylated flavonoids, phenolic acids, procyanidins, flavolignans and lignoids, most being described for the first time in the studied species, and some unpublished for the genus Erythroxylum and for the family Erythroxylaceae. The dereplication of the chloroform phases led to the annotation of 29 tropane alkaloids, some also being described for the first time in the genus and family of the studied species. From the ethyl acetate phase of E. simonis, the isolation of cinchonaines Ia and Ib, epicatechin, quercetin-O-hexoside, and biphenyl-3,3',4,4'- tetraol, described for the first time in the species, was isolated. Three compounds were isolated from the chloroform phase of E. revolutum, the protonated 6-(benzoyloxy)-3- (3,5-dimethoxy-4-hydroxybenzoyloxy)tropane, protonated 6-(benzoyloxy)-3-(3,4,5- trimethoxybenzoyloxy)tropane and protonated 6-(benzoyloxy)-3-(3,4,5- trimethoxycinnamoyloxy)tropane, reported for the first time in the species E. revolutum. This work contributed to the phytochemical knowledge of the genus Erythroxylum and demonstrates the efficiency and importance of using methodologies for guided isolation of secondary metabolites in research on natural products.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESDiversos metabólitos secundários de diferentes classes podem ser evidenciados em espécies do gênero Erythroxylum, com destaque para os flavonoides, terpenos e alcaloides do tipo tropânico, estes últimos sendo considerados marcadores do gênero. Por muitos desses compostos já se encontram descritos na literatura científica, metodologias modernas de triagem e identificação, como a desreplicação, se fazem necessárias para direcionar ao isolamento dos metabólitos de interesse, representando uma estratégia eficiente, rápida e segura. Este trabalho teve como objetivo traçar o perfil químico dos metabólitos secundários presentes nas fases clorofórmicas, acetato de etila e n-butanólicas das partes aéreas das espécies Erythroxylum simonis Plowman, Erythroxylum pauferrense Plowman, Erythroxylum pulchrum St. Hil. e Erythroxylum revolutum Mart. por metodologias de desreplicação. Para tanto, as fases foram analisadas por cromatografia líquida de alta eficiência acoplada a espectrometria de massas com ionização por electrospray, em seguida os experimentos foram repetidos com o cromatógrafo acoplado a um espectrômetro de massas de alta resolução, também com fonte de ionização por electrospray, as fases acetato de etila e n-butanólicas foram analisadas no modo negativo e as fases clorofórmicas no modo positivo. A anotação dos compostos foi realizada com base nos íons de suas moléculas desprotonadas ou protonadas, fórmulas moleculares, padrões de fragmentação e por comparação dos dados obtidos com os presentes na literatura científica. Os compostos não anotados completamente foram isolados e caracterizados por espectroscopia RMN de 1H e 13C. Por meio das análises realizadas foi possível traçar e comparar o perfil químico dos metabolitos secundários das espécies de Erythroxylum. A desreplicação das fases acetato de etila e n-butanólicas promoveu a anotação de 55 compostos fenólicos, se destacando os flavonoides glicosilados, ácidos fenólicos, procianidinas, flavolignanas e lignoides, a maioria sendo descritos pela primeira nas espécies do estudo, e alguns inéditos para o gênero Erythroxylum e para a família Erythroxylaceae. A desreplicação das fases clorofórmicas promoveu a anotação de 29 alcaloides tropânicos, alguns também sendo descritos pela primeira vez no gênero e na família das espécies estudadas. Da fase acetato de etila de E. simonis foi realizado o isolamento das cinchonaínas Ia e Ib, epicatequina, quercetina-O-hexosídeo, e do bifenil-3,3’,4,4’-tetraol, descritos pela primeira vez na espécie. Da fase clorofórmica de E. revolutum foi realizado o isolamento de três compostos, o 6-(benzoiloxi)-3-(3,5-dimetoxi-4- hidroxibenzoiloxi)tropano protonado, 6-(benzoiloxi)-3-(3,4,5- trimetoxibenzoiloxi)tropano protonado e 6-(benzoiloxi)-3-(3,4,5- trimetoxicinamoiloxi)tropano protonado, relatados pela primeira vez na espécie E. revolutum. Este trabalho contribuiu para os conhecimentos fitoquímicos do gênero Erythroxylum e demonstra a eficiência e a importância da utilização de metodologias de isolamento guiado de metabólitos secundários na pesquisa em produtos naturais.Universidade Federal da ParaíbaBrasilFarmacologiaPrograma de Pós-Graduação em Produtos Naturais e Sintéticos BioativosUFPBTavares, Josean FechineLattes não recuperado em 22/01/2024Dantas, César Augusto Gonçalves2024-01-22T17:10:12Z2023-04-262024-01-22T17:10:12Z2023-02-28info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesishttps://repositorio.ufpb.br/jspui/handle/123456789/29344porAttribution-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nd/3.0/br/info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFPBinstname:Universidade Federal da Paraíba (UFPB)instacron:UFPB2024-01-23T06:06:33Zoai:repositorio.ufpb.br:123456789/29344Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2024-01-23T06:06:33Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false |
dc.title.none.fl_str_mv |
Investigação fitoquímica de espécies do gênero Erythroxylum |
title |
Investigação fitoquímica de espécies do gênero Erythroxylum |
spellingShingle |
Investigação fitoquímica de espécies do gênero Erythroxylum Dantas, César Augusto Gonçalves Erythroxylaceae Alcaloides tropânicos Compostos fenólicos Espectroscopia Cromatografia Tropane alkaloids Phenolic compounds Spectroscopy Chromatography CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
title_short |
Investigação fitoquímica de espécies do gênero Erythroxylum |
title_full |
Investigação fitoquímica de espécies do gênero Erythroxylum |
title_fullStr |
Investigação fitoquímica de espécies do gênero Erythroxylum |
title_full_unstemmed |
Investigação fitoquímica de espécies do gênero Erythroxylum |
title_sort |
Investigação fitoquímica de espécies do gênero Erythroxylum |
author |
Dantas, César Augusto Gonçalves |
author_facet |
Dantas, César Augusto Gonçalves |
author_role |
author |
dc.contributor.none.fl_str_mv |
Tavares, Josean Fechine Lattes não recuperado em 22/01/2024 |
dc.contributor.author.fl_str_mv |
Dantas, César Augusto Gonçalves |
dc.subject.por.fl_str_mv |
Erythroxylaceae Alcaloides tropânicos Compostos fenólicos Espectroscopia Cromatografia Tropane alkaloids Phenolic compounds Spectroscopy Chromatography CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
topic |
Erythroxylaceae Alcaloides tropânicos Compostos fenólicos Espectroscopia Cromatografia Tropane alkaloids Phenolic compounds Spectroscopy Chromatography CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
description |
Several secondary metabolites of different classes can be evidenced in species of the genus Erythroxylum, with emphasis on flavonoids, terpenes and tropane alkaloids, the latter being considered markers of the genus. Because many of these compounds are already described in the scientific literature, modern screening and identification methodologies, such as dereplication, are necessary to direct the isolation of the metabolites of interest, representing an efficient, fast and safe strategy. This work aimed to trace the chemical profile of the secondary metabolites present in the chloroform, ethyl acetate and n-butanolic phases of the aerial parts of the species Erythroxylum simonis Plowman, Erythroxylum pauferrense Plowman, Erythroxylum pulchrum St. Hil. and Erythroxylum revolutum Mart. by dereplication methodologies. For this purpose, the phases were analyzed by high-performance liquid chromatography coupled to mass spectrometry with electrospray ionization, then the experiments were repeated with the chromatograph coupled to a high-resolution mass spectrometer, also with an electrospray ionization source, ethyl acetate and nbutanolic phases were analyzed in negative mode and chloroform phases in positive mode. The annotation of the compounds was carried out based on the ions of their deprotonated or protonated molecules, molecular formulas, fragmentation patterns and by comparing the data obtained with those present in the scientific literature. Compounds not fully annotated were isolated and characterized by 1H and 13C NMR spectroscopy. Through the analyzes carried out, it was possible to trace and compare the chemical profile of the secondary metabolites of the Erythroxylum species. The dereplication of the ethyl acetate and n-butanolic phases led to the annotation of 55 phenolic compounds, highlighting glycosylated flavonoids, phenolic acids, procyanidins, flavolignans and lignoids, most being described for the first time in the studied species, and some unpublished for the genus Erythroxylum and for the family Erythroxylaceae. The dereplication of the chloroform phases led to the annotation of 29 tropane alkaloids, some also being described for the first time in the genus and family of the studied species. From the ethyl acetate phase of E. simonis, the isolation of cinchonaines Ia and Ib, epicatechin, quercetin-O-hexoside, and biphenyl-3,3',4,4'- tetraol, described for the first time in the species, was isolated. Three compounds were isolated from the chloroform phase of E. revolutum, the protonated 6-(benzoyloxy)-3- (3,5-dimethoxy-4-hydroxybenzoyloxy)tropane, protonated 6-(benzoyloxy)-3-(3,4,5- trimethoxybenzoyloxy)tropane and protonated 6-(benzoyloxy)-3-(3,4,5- trimethoxycinnamoyloxy)tropane, reported for the first time in the species E. revolutum. This work contributed to the phytochemical knowledge of the genus Erythroxylum and demonstrates the efficiency and importance of using methodologies for guided isolation of secondary metabolites in research on natural products. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-04-26 2023-02-28 2024-01-22T17:10:12Z 2024-01-22T17:10:12Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufpb.br/jspui/handle/123456789/29344 |
url |
https://repositorio.ufpb.br/jspui/handle/123456789/29344 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
Attribution-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nd/3.0/br/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Farmacologia Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos UFPB |
publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Farmacologia Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos UFPB |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UFPB instname:Universidade Federal da Paraíba (UFPB) instacron:UFPB |
instname_str |
Universidade Federal da Paraíba (UFPB) |
instacron_str |
UFPB |
institution |
UFPB |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFPB |
collection |
Biblioteca Digital de Teses e Dissertações da UFPB |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB) |
repository.mail.fl_str_mv |
diretoria@ufpb.br|| diretoria@ufpb.br |
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1801843015370670080 |