Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica
Autor(a) principal: | |
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Data de Publicação: | 2022 |
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/123456789/26400 |
Resumo: | Research focused on the phytochemical and pharmacological knowledge of plant species has been increasing in order to contribute, together with ethnopharmacology and folk medicine, to the understanding of the biological responses promoted by these plants. The Boraginaceae family, due to its richness of species and great taxonomic complexity, studies on chemical composition are still scarce. However, research has revealed the presence of secondary metabolites of different classes such as terpenoids, naphthoquinones, flavonoids, phenylpropanoids, alkaloids and lignans. Heliotropium angiospermum, known as "cat's tail", is popularly used in inflammation, wound healing, dysentery and diarrhea. Euploca procumbens, has several popular names and in an ethnomedicinal study it was considered toxic because it has pyrrolizidine alkaloids in its constitution. This work aimed to contribute to the expansion of chemical knowledge by isolating, identifying and/or characterizing new secondary metabolites and evaluating the biological activity of constituents of species of the Boraginaceae family: H. angiospermum and E. procumbens. The plants of both species were collected in the municipality of Campina Grande, state of Paraíba. Each exsiccate was deposited in the Herbarium Arruda Câmara (HACAM) on Campus I of the State University of Paraíba. The plant material, after drying at a temperature of 40 °C for 96 hours, and crushed in a knife mill, was subjected to macerations with 96% ethanol with an interval of 72 h, this process being repeated five times, obtaining the extracts ethanol from the aerial parts and roots of the two species under study. An aliquot of each ethanolic extract was subjected to successive partitions with hexane, chloroform, ethyl acetate and n-butanol and concentrated on a rotary evaporator, obtaining the respective phases. Subsequently, they were submitted to a Sephadex LH-20 chromatographic column and eluted with methanol (100%) to obtain the fractions. An aliquot of Fr3 aerial parts (acetate phase) and Fr3 roots (acetate phase) of H. angiospermum and, Fr5 aerial parts (acetate phase), Fr5 roots (acetate phase) and Fr5 roots (n-butanol phase) of E. procumbens were submitted to the development of an analytical chromatographic method and later transferred to a preparative scale resulting in the isolation of ten compounds, a sucrose diester lignan of the aryldihydronaphthalene type (1), trigonotin A (2), rosmarinic acid (3), narcissine (4) and ethyl lithospermate (5) from the species H. angiospermum and an euploic acid (6), lithospermic acid B (7), lithospermic acid (8), 9´´-methyl lithospermate (9) and luteolin-7-O-glycoside (10) of E. procumbens. Composites 1 and 6 did not induce cytotoxic effects in J774 macrophages, and from the levels of nitric oxide and pro-inflammatory cytokines IL-1β produced by stimulated macrophages, 1 and 6 inhibited the production and/or release of these mediators, with efficacy like that of dexamethasone, considered the anti-inflammatory gold standard. Therefore, these results evidence the anti-inflammatory potential of 1 and 6. |
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Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológicaFamília BoraginaceaeHeliotropiumEuplocaElucidação estruturalCitotoxicidadeÁcidos fenólicosInterleucina-1βInibição de ONLignana arildihidronaftalenoÉsteres de sacaroseBoraginaceae familyStructural elucidationCytotoxicityPhenolic acidsInterleukin-1βON inhibitionAryldihydronaphthalene lignanSucrose estersCNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIAResearch focused on the phytochemical and pharmacological knowledge of plant species has been increasing in order to contribute, together with ethnopharmacology and folk medicine, to the understanding of the biological responses promoted by these plants. The Boraginaceae family, due to its richness of species and great taxonomic complexity, studies on chemical composition are still scarce. However, research has revealed the presence of secondary metabolites of different classes such as terpenoids, naphthoquinones, flavonoids, phenylpropanoids, alkaloids and lignans. Heliotropium angiospermum, known as "cat's tail", is popularly used in inflammation, wound healing, dysentery and diarrhea. Euploca procumbens, has several popular names and in an ethnomedicinal study it was considered toxic because it has pyrrolizidine alkaloids in its constitution. This work aimed to contribute to the expansion of chemical knowledge by isolating, identifying and/or characterizing new secondary metabolites and evaluating the biological activity of constituents of species of the Boraginaceae family: H. angiospermum and E. procumbens. The plants of both species were collected in the municipality of Campina Grande, state of Paraíba. Each exsiccate was deposited in the Herbarium Arruda Câmara (HACAM) on Campus I of the State University of Paraíba. The plant material, after drying at a temperature of 40 °C for 96 hours, and crushed in a knife mill, was subjected to macerations with 96% ethanol with an interval of 72 h, this process being repeated five times, obtaining the extracts ethanol from the aerial parts and roots of the two species under study. An aliquot of each ethanolic extract was subjected to successive partitions with hexane, chloroform, ethyl acetate and n-butanol and concentrated on a rotary evaporator, obtaining the respective phases. Subsequently, they were submitted to a Sephadex LH-20 chromatographic column and eluted with methanol (100%) to obtain the fractions. An aliquot of Fr3 aerial parts (acetate phase) and Fr3 roots (acetate phase) of H. angiospermum and, Fr5 aerial parts (acetate phase), Fr5 roots (acetate phase) and Fr5 roots (n-butanol phase) of E. procumbens were submitted to the development of an analytical chromatographic method and later transferred to a preparative scale resulting in the isolation of ten compounds, a sucrose diester lignan of the aryldihydronaphthalene type (1), trigonotin A (2), rosmarinic acid (3), narcissine (4) and ethyl lithospermate (5) from the species H. angiospermum and an euploic acid (6), lithospermic acid B (7), lithospermic acid (8), 9´´-methyl lithospermate (9) and luteolin-7-O-glycoside (10) of E. procumbens. Composites 1 and 6 did not induce cytotoxic effects in J774 macrophages, and from the levels of nitric oxide and pro-inflammatory cytokines IL-1β produced by stimulated macrophages, 1 and 6 inhibited the production and/or release of these mediators, with efficacy like that of dexamethasone, considered the anti-inflammatory gold standard. Therefore, these results evidence the anti-inflammatory potential of 1 and 6.NenhumaPesquisas voltadas para os conhecimentos fitoquímicos e farmacológicos de espécies vegetais vêm aumentando com intuito de contribuir, juntamente com a etnofarmacologia e a medicina popular, na compreensão das respostas biológicas promovidas por esses vegetais. Na família Boraginaceae, por apresentar uma riqueza de espécies e uma grande complexidade taxonômica, ainda são escassos os estudos sobre composição química. Porém, pesquisas revelaram a presença de metabólitos secundários de diversas classes como terpenoides, naftoquinonas, flavonoides, fenilpropanoides, alcaloides e lignanas. Heliotropium angiospermum, conhecida como “cauda de gato”, é utilizada popularmente na inflamação, cicatrização de feridas, disenteria e diarreia. Euploca procumbens, apresenta diversos nomes populares e num estudo etnomedicinal foi considerada tóxica por apresentar alcaloides pirrolizidínicos em sua constituição. Este trabalho teve como objetivo contribuir para a ampliação do conhecimento químico isolando, identificando e/ou caracterizando novos metabólitos secundários e avaliando atividade biológica dos constituintes de espécies da família Boraginaceae: H. angiospermum e E. procumbens. As plantas das duas espécies foram coletadas no município de Campina Grande, estado da Paraíba. Cada exsicata foi depositada no Herbário Arruda Câmara (HACAM) do Campus I da Universidade Estadual da Paraíba. O material vegetal, após seco sob temperatura de 40 ºC durante 96 horas, e triturado em moinho de facas, foi submetido a macerações com etanol a 96% com intervalo de 72 h, sendo esse processo repetido por cinco vezes, obtendo-se os extratos etanólicos das partes aéreas e raízes das duas espécies em estudo. Uma alíquota de cada extrato etanólico foi submetida a sucessivas partições com hexano, clorofórmio, acetato de etila e n-butanol e concentradas em evaporador rotativo obtendo-se as respectivas fases. Posteriormente, foram submetidas à coluna cromatográfica com Sephadex LH-20 e eluída com metanol (100%), obtendo-se as frações. Uma alíquota da Fr3 partes aéreas (fase acetato) e Fr3 raízes (fase acetato) de H. angiospermum e, Fr5 partes aéreas (fase acetato), Fr5 raízes (fase acetato) e Fr5 raízes (fase n-butanol) de E. procumbens foram submetidas ao desenvolvimento de um método cromatográfico analítico e posteriormente transposto para escala preparativa resultando no isolamento de dez compostos, uma lignana diéster de sacarose do tipo arildihidronaftaleno (1), trigonotina A (2), ácido rosmarínico (3), narcissina (4) e litospermato de etila (5) da espécie H. angiospermum e um ácido euploico (6), ácido litospérmico B (7), ácido litospérmico (8), 9´´-metil litospermato (9) e luteolina-7-O-glicosídeo (10) de E. procumbens. Os compostos 1 e 6 não induziram efeitos citotóxicos em macrófagos J774, bem como, a partir dos níveis de óxido nítrico e citocinas pró-inflamatória IL-1β produzida por macrófagos estimulados, 1 e 6 inibiram a produção e/ou liberação desses mediadores, com eficácia semelhante à da dexametasona, considerada o padrão-ouro anti-inflamatório. Portanto, esses resultados evidenciam o potencial anti-inflamatório de 1 e 6.Universidade Federal da ParaíbaBrasilFarmacologiaPrograma de Pós-Graduação em Produtos Naturais e Sintéticos BioativosUFPBSilva, Marcelo Sobral dahttp://lattes.cnpq.br/5980170934785365Fechine, Ivana Mariahttp://lattes.cnpq.br/5689715833582093Santos, George Luís Dias dos2023-03-07T14:13:50Z2023-01-302023-03-07T14:13:50Z2022-11-28info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesishttps://repositorio.ufpb.br/jspui/handle/123456789/26400porAttribution-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:UFPB2023-05-22T12:29:19Zoai:repositorio.ufpb.br:123456789/26400Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2023-05-22T12:29:19Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false |
dc.title.none.fl_str_mv |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica |
title |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica |
spellingShingle |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica Santos, George Luís Dias dos Família Boraginaceae Heliotropium Euploca Elucidação estrutural Citotoxicidade Ácidos fenólicos Interleucina-1β Inibição de ON Lignana arildihidronaftaleno Ésteres de sacarose Boraginaceae family Structural elucidation Cytotoxicity Phenolic acids Interleukin-1β ON inhibition Aryldihydronaphthalene lignan Sucrose esters CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
title_short |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica |
title_full |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica |
title_fullStr |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica |
title_full_unstemmed |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica |
title_sort |
Estudo fitoquímico de espécies dos gêneros Heliotropium e Euploca (Boraginaceae): busca de moléculas com atividade biológica |
author |
Santos, George Luís Dias dos |
author_facet |
Santos, George Luís Dias dos |
author_role |
author |
dc.contributor.none.fl_str_mv |
Silva, Marcelo Sobral da http://lattes.cnpq.br/5980170934785365 Fechine, Ivana Maria http://lattes.cnpq.br/5689715833582093 |
dc.contributor.author.fl_str_mv |
Santos, George Luís Dias dos |
dc.subject.por.fl_str_mv |
Família Boraginaceae Heliotropium Euploca Elucidação estrutural Citotoxicidade Ácidos fenólicos Interleucina-1β Inibição de ON Lignana arildihidronaftaleno Ésteres de sacarose Boraginaceae family Structural elucidation Cytotoxicity Phenolic acids Interleukin-1β ON inhibition Aryldihydronaphthalene lignan Sucrose esters CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
topic |
Família Boraginaceae Heliotropium Euploca Elucidação estrutural Citotoxicidade Ácidos fenólicos Interleucina-1β Inibição de ON Lignana arildihidronaftaleno Ésteres de sacarose Boraginaceae family Structural elucidation Cytotoxicity Phenolic acids Interleukin-1β ON inhibition Aryldihydronaphthalene lignan Sucrose esters CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
description |
Research focused on the phytochemical and pharmacological knowledge of plant species has been increasing in order to contribute, together with ethnopharmacology and folk medicine, to the understanding of the biological responses promoted by these plants. The Boraginaceae family, due to its richness of species and great taxonomic complexity, studies on chemical composition are still scarce. However, research has revealed the presence of secondary metabolites of different classes such as terpenoids, naphthoquinones, flavonoids, phenylpropanoids, alkaloids and lignans. Heliotropium angiospermum, known as "cat's tail", is popularly used in inflammation, wound healing, dysentery and diarrhea. Euploca procumbens, has several popular names and in an ethnomedicinal study it was considered toxic because it has pyrrolizidine alkaloids in its constitution. This work aimed to contribute to the expansion of chemical knowledge by isolating, identifying and/or characterizing new secondary metabolites and evaluating the biological activity of constituents of species of the Boraginaceae family: H. angiospermum and E. procumbens. The plants of both species were collected in the municipality of Campina Grande, state of Paraíba. Each exsiccate was deposited in the Herbarium Arruda Câmara (HACAM) on Campus I of the State University of Paraíba. The plant material, after drying at a temperature of 40 °C for 96 hours, and crushed in a knife mill, was subjected to macerations with 96% ethanol with an interval of 72 h, this process being repeated five times, obtaining the extracts ethanol from the aerial parts and roots of the two species under study. An aliquot of each ethanolic extract was subjected to successive partitions with hexane, chloroform, ethyl acetate and n-butanol and concentrated on a rotary evaporator, obtaining the respective phases. Subsequently, they were submitted to a Sephadex LH-20 chromatographic column and eluted with methanol (100%) to obtain the fractions. An aliquot of Fr3 aerial parts (acetate phase) and Fr3 roots (acetate phase) of H. angiospermum and, Fr5 aerial parts (acetate phase), Fr5 roots (acetate phase) and Fr5 roots (n-butanol phase) of E. procumbens were submitted to the development of an analytical chromatographic method and later transferred to a preparative scale resulting in the isolation of ten compounds, a sucrose diester lignan of the aryldihydronaphthalene type (1), trigonotin A (2), rosmarinic acid (3), narcissine (4) and ethyl lithospermate (5) from the species H. angiospermum and an euploic acid (6), lithospermic acid B (7), lithospermic acid (8), 9´´-methyl lithospermate (9) and luteolin-7-O-glycoside (10) of E. procumbens. Composites 1 and 6 did not induce cytotoxic effects in J774 macrophages, and from the levels of nitric oxide and pro-inflammatory cytokines IL-1β produced by stimulated macrophages, 1 and 6 inhibited the production and/or release of these mediators, with efficacy like that of dexamethasone, considered the anti-inflammatory gold standard. Therefore, these results evidence the anti-inflammatory potential of 1 and 6. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-11-28 2023-03-07T14:13:50Z 2023-01-30 2023-03-07T14:13:50Z |
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/123456789/26400 |
url |
https://repositorio.ufpb.br/jspui/handle/123456789/26400 |
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 |
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Universidade Federal da Paraíba (UFPB) |
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UFPB |
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UFPB |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFPB |
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Biblioteca Digital de Teses e Dissertações da UFPB |
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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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1801843007435046912 |