Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UEFS |
Texto Completo: | http://tede2.uefs.br:8080/handle/tede/1398 |
Resumo: | Studies corroborate the popular use of species of the genus Polygala, however Polygala boliviensis A.W. Benn (Polygalaceae), found in the semi-arid region of Bahia, has few chemical and pharmacological studies. Thus, this work aimed to conduct a pharmacognostic study and the biological activities of P. boliviensis. The collection of the aerial parts and roots of the species, for the different stages, was performed at the UEFS campus, in Feira de Santana, Bahia. For the isolation of secondary metabolites, methanolic extract was prepared by maceration, followed by partition with hexane, chloroform and ethyl acetate, and successive procedures by column chromatography. The identification of the isolated metabolites was performed by one- and two-dimensional NMR, resulting in the chemical structures of 1,3,5-trihydroxy-2-methoxyxanthone, α-spinasterol, as well as a coumarin and fatty acid mixture that are in confirmation phase. In the evaluation of biological activity, the coumarins auraptene and polygalen, previously isolated from P. boliviensis, were evaluated by MTT test and in vitro antiplasmodial activity against chloroquine-resistant strain of Plasmodium falciparum (W2), and showed IC50 = 13.46 ± 0.03 μM and EC50 = 0.171 ± 0.016 for auraptene; and above 100 μM and 0.164 ± 0.012 for poligalen, resulting in the selectivity index of 78.71 and 609.76, respectively. These coumarins were also subjected to docking-based inverse virtual screening using P. falciparum targets from BraMMT, demonstrating better affinity to purine nulceoside phosphorylase and dihydroorotate dehydrogenase enzymes. We also evaluated the seasonal variation of the chemical composition through the identification and quantification of secondary metabolites by HPLC-DAD; the antioxidant activity, through the DPPH-free radical scavenging test and inhibition of β-carotene auto-oxidation; and the lethality against Artemia salina. By this method, gallic acid, rutin, poligalen, auraptene, and 7 unknown major peaks were identified, which through UV spectra, are believed to be phenolic acids, flavonoids, xanthones, coumarins, and styrylpyrones. Although there was no seasonal variation in the yield of extracts and chemical profile, there was quantitative variation of metabolites, antioxidant activity and lethality against A. salina. For the anatomical characterization light microscopy was used, analyzing samples included in historesin and stained with toluidine blue, while for histochemistry, the samples were sectioned in cryomicrotome and submitted to different tests. P. boliviensis showed amphistomatic leaves and non-glandular trichomes on the leaves and stems, in addition to lysigenous secretory cavities found in the leaves and responsible for lipid secretion. This study contributes to the chemical characterization of P. boliviensis, as well as to taxonomic delimitations, facilitating the differentiation between morphologically similar species, and corroborating the chemosystematics of the genus Polygala. Added to this, the diversity of the chemical composition and antiplasmodial activity demonstrated by auraptene and poligalen reinforce the phytotherapeutic potential of the species, but as seasonality influences the amount of these and other secondary metabolites, it should be considered, facilitating the determination of the collection period or ideal cultivation conditions, to obtain the metabolites of interest. |
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Brandão, Hugo Neves82693560500https://orcid.org/0000-0001-5198-5039http://lattes.cnpq.br/8057581458002753Alves, Clayton Queiroz75077523568lattes.cnpq.br/9188574132632625Martins, Fabiano Machado90853440000http://lattes.cnpq.br/699157077739977504224304554http://lattes.cnpq.br/7170628262119833Silva, Danielle Figuerêdo da2022-09-02T13:46:59Z2020-09-29SILVA, Danielle Figuerêdo da. Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn. 2020. 115 f. Tese (Doutorado Acadêmico em Recursos Genéticos Vegetais) - Departamento de Ciências Biológicas, Universidade Estadual de Feira de Santana, Feira de Santana, 2020.http://tede2.uefs.br:8080/handle/tede/1398Studies corroborate the popular use of species of the genus Polygala, however Polygala boliviensis A.W. Benn (Polygalaceae), found in the semi-arid region of Bahia, has few chemical and pharmacological studies. Thus, this work aimed to conduct a pharmacognostic study and the biological activities of P. boliviensis. The collection of the aerial parts and roots of the species, for the different stages, was performed at the UEFS campus, in Feira de Santana, Bahia. For the isolation of secondary metabolites, methanolic extract was prepared by maceration, followed by partition with hexane, chloroform and ethyl acetate, and successive procedures by column chromatography. The identification of the isolated metabolites was performed by one- and two-dimensional NMR, resulting in the chemical structures of 1,3,5-trihydroxy-2-methoxyxanthone, α-spinasterol, as well as a coumarin and fatty acid mixture that are in confirmation phase. In the evaluation of biological activity, the coumarins auraptene and polygalen, previously isolated from P. boliviensis, were evaluated by MTT test and in vitro antiplasmodial activity against chloroquine-resistant strain of Plasmodium falciparum (W2), and showed IC50 = 13.46 ± 0.03 μM and EC50 = 0.171 ± 0.016 for auraptene; and above 100 μM and 0.164 ± 0.012 for poligalen, resulting in the selectivity index of 78.71 and 609.76, respectively. These coumarins were also subjected to docking-based inverse virtual screening using P. falciparum targets from BraMMT, demonstrating better affinity to purine nulceoside phosphorylase and dihydroorotate dehydrogenase enzymes. We also evaluated the seasonal variation of the chemical composition through the identification and quantification of secondary metabolites by HPLC-DAD; the antioxidant activity, through the DPPH-free radical scavenging test and inhibition of β-carotene auto-oxidation; and the lethality against Artemia salina. By this method, gallic acid, rutin, poligalen, auraptene, and 7 unknown major peaks were identified, which through UV spectra, are believed to be phenolic acids, flavonoids, xanthones, coumarins, and styrylpyrones. Although there was no seasonal variation in the yield of extracts and chemical profile, there was quantitative variation of metabolites, antioxidant activity and lethality against A. salina. For the anatomical characterization light microscopy was used, analyzing samples included in historesin and stained with toluidine blue, while for histochemistry, the samples were sectioned in cryomicrotome and submitted to different tests. P. boliviensis showed amphistomatic leaves and non-glandular trichomes on the leaves and stems, in addition to lysigenous secretory cavities found in the leaves and responsible for lipid secretion. This study contributes to the chemical characterization of P. boliviensis, as well as to taxonomic delimitations, facilitating the differentiation between morphologically similar species, and corroborating the chemosystematics of the genus Polygala. Added to this, the diversity of the chemical composition and antiplasmodial activity demonstrated by auraptene and poligalen reinforce the phytotherapeutic potential of the species, but as seasonality influences the amount of these and other secondary metabolites, it should be considered, facilitating the determination of the collection period or ideal cultivation conditions, to obtain the metabolites of interest.Estudos corroboram o uso popular de espécies do gênero Polygala, no entanto Polygala boliviensis A.W. Benn (Polygalaceae), encontrada no semiárido baiano, apresenta poucos estudos químicos e farmacológicos. Nesse sentido, este trabalho teve como objetivo realizar o estudo farmacognóstico e das atividades biológicas de P. boliviensis. A coleta das partes aéreas e raízes da espécie, para as diferentes etapas, foi realizada no campus da UEFS, em Feira de Santana, Bahia. Para o isolamento dos metabólitos secundários, foi preparado extrato metanólico por maceração, seguido de partição com hexano, clorofórmio e acetato de etila, e sucessivos procedimentos por cromatografia em coluna. A identificação dos metabólitos isolados foi realizada por RMN uni e bidimensionais, resultando nas estruturas químicas da 1,3,5-triidróxi-2-metóxi-xantona, do α-espinasterol, além de uma cumarina e mistura de ácido graxo que se encontram em fase de confirmação. Na avaliação da atividade biológica, as cumarinas aurapteno e poligaleno, isoladas anteriormente de P. boliviensis, foram avaliadas pelo teste de MTT e atividade antiplasmodial in vitro contra cepa cloroquina-resistente de Plasmodium falciparum (W2), e demonstraram CI50 = 13,46 ± 0,03 μM e CE50 = 0,171 ± 0,016 para aurapteno; e acima de 100 μM e 0,164 ± 0,012 para poligaleno, resultando no índice de seletividade de 78,71 e 609,76, respectivamente. Essas cumarinas foram também submetidas à triagem virtual inversa baseada em docking, utilizando os alvos de P. falciparum do BraMMT, demonstrando melhor afinidade com enzimas purina nulceosídeo fosforilase e diidroorotato desidrogenase. Também foi realizada a avaliação da variação sazonal da composição química através da identificação e quantificação dos metabólitos secundários por CLAE-DAD; da atividade antioxidante, através do teste de sequestro do radical livre DPPH• e inibição da auto oxidação do β-caroteno; e da letalidade frente à Artemia salina. Por esse método, foram identificados ácido gálico, rutina, poligaleno, aurapteno e 7 picos majoritários desconhecidos, que através de espectros no UV, acredita-se tratar de ácidos fenólicos, flavonoides, xantonas, cumarinas e estirilpironas. Apesar de não haver variação sazonal no rendimento dos extratos e no perfil químico, houve variação quantitativa dos metabólitos, da atividade antioxidante e letalidade frente à A. salina. Para a caracterização anatômica foi utilizada microscopia de luz, analizando amostras incluídas em historesina e coradas com azul de toluidina, enquanto para a histoquímica, as amostras foram seccionadas em criomicrótomo e submetidas a diferentes testes. P. boliviensis apresentou folhas anfiestomáticas e tricomas não glandulares nas folhas e caules, além de cavidades secretoras lisígenas encontradas nas folhas e responsáveis pela secreção de lipídios. O presente estudo contribui com a caracterização química da P. boliviensis, bem como para delimitações taxonômicas, facilitando a diferenciação entre espécies morfologicamente semelhantes, além de corroborar com a quimiossistemática do gênero Polygala. Somado a isso, a diversidade da composição química e atividade antiplasmodial demonstrada pelo aurapteno e poligaleno reforçam o potencial fitoterapêutico da espécie, porém como a sazonalidade influencia na quantidade desses e de outros metabólitos secundários, deve ser considerada, facilitando a determinação do período de coleta ou condições de cultivo ideais, para obtenção dos metabólitos de interesse.Submitted by Renata Aline Souza Silva (rassilva@uefs.br) on 2022-09-02T13:46:59Z No. of bitstreams: 1 Tese_Danielle Figuerêdo da Silva 2020.pdf: 4372485 bytes, checksum: 32db4e67a732eeca14feacfcb9b83b6c (MD5)Made available in DSpace on 2022-09-02T13:46:59Z (GMT). No. of bitstreams: 1 Tese_Danielle Figuerêdo da Silva 2020.pdf: 4372485 bytes, checksum: 32db4e67a732eeca14feacfcb9b83b6c (MD5) Previous issue date: 2020-09-29Fundação de Amparo à Pesquisa do Estado da Bahia - FAPEBapplication/pdfporUniversidade Estadual de Feira de SantanaDoutorado Acadêmico em Recursos Genéticos VegetaisUEFSBrasilDEPARTAMENTO DE CIÊNCIAS BIOLÓGICASAnatomiaAtividade biológicaHistoquímicaMetabólitos secundáriosSazonalidadeAnatomyBiological activityHistochemistrySeasonalitySecondary metabolitesFARMACIA::FARMACOGNOSIACIENCIAS BIOLOGICASCIENCIAS BIOLOGICAS::BIOQUIMICAEstudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. 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dc.title.por.fl_str_mv |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn |
title |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn |
spellingShingle |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn Silva, Danielle Figuerêdo da Anatomia Atividade biológica Histoquímica Metabólitos secundários Sazonalidade Anatomy Biological activity Histochemistry Seasonality Secondary metabolites FARMACIA::FARMACOGNOSIA CIENCIAS BIOLOGICAS CIENCIAS BIOLOGICAS::BIOQUIMICA |
title_short |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn |
title_full |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn |
title_fullStr |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn |
title_full_unstemmed |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn |
title_sort |
Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn |
author |
Silva, Danielle Figuerêdo da |
author_facet |
Silva, Danielle Figuerêdo da |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Brandão, Hugo Neves |
dc.contributor.advisor1ID.fl_str_mv |
82693560500 https://orcid.org/0000-0001-5198-5039 |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/8057581458002753 |
dc.contributor.advisor-co1.fl_str_mv |
Alves, Clayton Queiroz |
dc.contributor.advisor-co1ID.fl_str_mv |
75077523568 |
dc.contributor.advisor-co1Lattes.fl_str_mv |
lattes.cnpq.br/9188574132632625 |
dc.contributor.advisor-co2.fl_str_mv |
Martins, Fabiano Machado |
dc.contributor.advisor-co2ID.fl_str_mv |
90853440000 |
dc.contributor.advisor-co2Lattes.fl_str_mv |
http://lattes.cnpq.br/6991570777399775 |
dc.contributor.authorID.fl_str_mv |
04224304554 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7170628262119833 |
dc.contributor.author.fl_str_mv |
Silva, Danielle Figuerêdo da |
contributor_str_mv |
Brandão, Hugo Neves Alves, Clayton Queiroz Martins, Fabiano Machado |
dc.subject.por.fl_str_mv |
Anatomia Atividade biológica Histoquímica Metabólitos secundários Sazonalidade |
topic |
Anatomia Atividade biológica Histoquímica Metabólitos secundários Sazonalidade Anatomy Biological activity Histochemistry Seasonality Secondary metabolites FARMACIA::FARMACOGNOSIA CIENCIAS BIOLOGICAS CIENCIAS BIOLOGICAS::BIOQUIMICA |
dc.subject.eng.fl_str_mv |
Anatomy Biological activity Histochemistry Seasonality Secondary metabolites |
dc.subject.cnpq.fl_str_mv |
FARMACIA::FARMACOGNOSIA CIENCIAS BIOLOGICAS CIENCIAS BIOLOGICAS::BIOQUIMICA |
description |
Studies corroborate the popular use of species of the genus Polygala, however Polygala boliviensis A.W. Benn (Polygalaceae), found in the semi-arid region of Bahia, has few chemical and pharmacological studies. Thus, this work aimed to conduct a pharmacognostic study and the biological activities of P. boliviensis. The collection of the aerial parts and roots of the species, for the different stages, was performed at the UEFS campus, in Feira de Santana, Bahia. For the isolation of secondary metabolites, methanolic extract was prepared by maceration, followed by partition with hexane, chloroform and ethyl acetate, and successive procedures by column chromatography. The identification of the isolated metabolites was performed by one- and two-dimensional NMR, resulting in the chemical structures of 1,3,5-trihydroxy-2-methoxyxanthone, α-spinasterol, as well as a coumarin and fatty acid mixture that are in confirmation phase. In the evaluation of biological activity, the coumarins auraptene and polygalen, previously isolated from P. boliviensis, were evaluated by MTT test and in vitro antiplasmodial activity against chloroquine-resistant strain of Plasmodium falciparum (W2), and showed IC50 = 13.46 ± 0.03 μM and EC50 = 0.171 ± 0.016 for auraptene; and above 100 μM and 0.164 ± 0.012 for poligalen, resulting in the selectivity index of 78.71 and 609.76, respectively. These coumarins were also subjected to docking-based inverse virtual screening using P. falciparum targets from BraMMT, demonstrating better affinity to purine nulceoside phosphorylase and dihydroorotate dehydrogenase enzymes. We also evaluated the seasonal variation of the chemical composition through the identification and quantification of secondary metabolites by HPLC-DAD; the antioxidant activity, through the DPPH-free radical scavenging test and inhibition of β-carotene auto-oxidation; and the lethality against Artemia salina. By this method, gallic acid, rutin, poligalen, auraptene, and 7 unknown major peaks were identified, which through UV spectra, are believed to be phenolic acids, flavonoids, xanthones, coumarins, and styrylpyrones. Although there was no seasonal variation in the yield of extracts and chemical profile, there was quantitative variation of metabolites, antioxidant activity and lethality against A. salina. For the anatomical characterization light microscopy was used, analyzing samples included in historesin and stained with toluidine blue, while for histochemistry, the samples were sectioned in cryomicrotome and submitted to different tests. P. boliviensis showed amphistomatic leaves and non-glandular trichomes on the leaves and stems, in addition to lysigenous secretory cavities found in the leaves and responsible for lipid secretion. This study contributes to the chemical characterization of P. boliviensis, as well as to taxonomic delimitations, facilitating the differentiation between morphologically similar species, and corroborating the chemosystematics of the genus Polygala. Added to this, the diversity of the chemical composition and antiplasmodial activity demonstrated by auraptene and poligalen reinforce the phytotherapeutic potential of the species, but as seasonality influences the amount of these and other secondary metabolites, it should be considered, facilitating the determination of the collection period or ideal cultivation conditions, to obtain the metabolites of interest. |
publishDate |
2020 |
dc.date.issued.fl_str_mv |
2020-09-29 |
dc.date.accessioned.fl_str_mv |
2022-09-02T13:46:59Z |
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.citation.fl_str_mv |
SILVA, Danielle Figuerêdo da. Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn. 2020. 115 f. Tese (Doutorado Acadêmico em Recursos Genéticos Vegetais) - Departamento de Ciências Biológicas, Universidade Estadual de Feira de Santana, Feira de Santana, 2020. |
dc.identifier.uri.fl_str_mv |
http://tede2.uefs.br:8080/handle/tede/1398 |
identifier_str_mv |
SILVA, Danielle Figuerêdo da. Estudo farmacognóstico e atividades biológicas de Polygala boliviensis A.W. Benn. 2020. 115 f. Tese (Doutorado Acadêmico em Recursos Genéticos Vegetais) - Departamento de Ciências Biológicas, Universidade Estadual de Feira de Santana, Feira de Santana, 2020. |
url |
http://tede2.uefs.br:8080/handle/tede/1398 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.program.fl_str_mv |
-3267524094848184949 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 |
dc.relation.department.fl_str_mv |
5026123383450589282 |
dc.relation.cnpq.fl_str_mv |
6679646253015605836 -3439178843068202161 893477990329266114 |
dc.relation.sponsorship.fl_str_mv |
-8233071094704392586 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Estadual de Feira de Santana |
dc.publisher.program.fl_str_mv |
Doutorado Acadêmico em Recursos Genéticos Vegetais |
dc.publisher.initials.fl_str_mv |
UEFS |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
DEPARTAMENTO DE CIÊNCIAS BIOLÓGICAS |
publisher.none.fl_str_mv |
Universidade Estadual de Feira de Santana |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UEFS instname:Universidade Estadual de Feira de Santana (UEFS) instacron:UEFS |
instname_str |
Universidade Estadual de Feira de Santana (UEFS) |
instacron_str |
UEFS |
institution |
UEFS |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UEFS |
collection |
Biblioteca Digital de Teses e Dissertações da UEFS |
bitstream.url.fl_str_mv |
http://tede2.uefs.br:8080/bitstream/tede/1398/2/Tese_Danielle+Figuer%C3%AAdo+da+Silva+2020.pdf http://tede2.uefs.br:8080/bitstream/tede/1398/1/license.txt |
bitstream.checksum.fl_str_mv |
32db4e67a732eeca14feacfcb9b83b6c 7b5ba3d2445355f386edab96125d42b7 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações da UEFS - Universidade Estadual de Feira de Santana (UEFS) |
repository.mail.fl_str_mv |
bcuefs@uefs.br|| bcref@uefs.br||bcuefs@uefs.br |
_version_ |
1800214587596865536 |