Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)

Detalhes bibliográficos
Autor(a) principal: Martins, Carla de Moura
Data de Publicação: 2017
Tipo de documento: Tese
Idioma: por
Título da fonte: Repositório Institucional da UFU
Texto Completo: https://repositorio.ufu.br/handle/123456789/19563
http://dx.doi.org/10.14393/ufu.te.2017.97
Resumo: The plant Inga laurina is found in Brazilian cerrado and there are few studies in the literature about this species, so the objective of this work was to identify the chemical constituents of bark and leaves that are responsible for the biological activities observed. Antioxidant activity, antifungal, a-amylase inhibitor, antibacterial and antiprotozoal activity were analyzed. The results showed that the extracts and fractions of the leaves have a great amount of phenolic compounds, especially from the ethyl acetate fraction of leaves (FAE-F), which presented high total phenol content and flavonoids, a result that can explain the antioxidant activity evaluated by the method of DPPH (2,2-diphenyl-1-pictytoy^^yl) radical, the a-amylase enzyme inhibition and the antifungal activity for Candida glabrata. From this fraction, the flavonoid myricetin-3- O-rhamnoside was isolated and eleven phenolic compounds were identified by mass spectrometry (MS): gallic acid, (epi)-gallocatechin, methyl gallic acid derivative, ethyl gallate, myricetin-O-(O-galloyl)-hexoside, myricetin-3-O-galactoside, myricetin galloyl rhamnoside, myricetin, quercetin-3-O-rhamnoside, quercetin-3-O-(2"-galloyl)- rhamnoside and quercetin. After column fractionation of FAE-F, myricetin-3-O-acetyl- rhamnoside, digalloylquinic acid, myricetin-3-O-rhamnose-3'-O-rhamnose, trigalloylquinic acid and vanillic acid, were identified by MS. Extracts and fractions of the bark also showed a high content of phenolic compounds, such as total phenols and proanthocyanidins, especially the ethyl acetate, n-butanol and methanol fractions, which were the most active samples for inhibition of the a-amylase enzyme, antioxidant activity and antifungal activity for the Candida species tested. From the ethyl acetate fraction of the bark (FAEI-C and FAEII-C) were isolated unreported flavonoids and proanthocyanidins in the genus Inga such as 4'-O-methylgallocatechin, gallocatechin, gallocatechin-(4a-8)-4'-O-methylgalocatechin, epigallocatechin-(2—>O—>7,4—>8)-4'-O- methylgallocatechin and epigallocatechin-3-O-galoyl- (2—>O—>7,4—>8)-4'-O- methylgallocatechin. In addition, the compounds epigallocatechin-3-O-gallate, epicatechin-3-O-gallate, 4'-O-methyl-epigallocatechin-3-O-gallate, epigallocatechin-3- O-(3",4"-O-dimethyl) gallate, p-cumaric acid and prodelphinidine B-4 were identified by MS. Therefore, the I. laurina plant was characterized as a promising species as a source of biologically active phenolic compounds.
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spelling Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)QuímicaInga (Botânica) - ComposiçãoAntioxidantesCerradosInga laurinaAntifúngicoa-AmilaseBrazilian CerradoAntioxidantAntifungalCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAThe plant Inga laurina is found in Brazilian cerrado and there are few studies in the literature about this species, so the objective of this work was to identify the chemical constituents of bark and leaves that are responsible for the biological activities observed. Antioxidant activity, antifungal, a-amylase inhibitor, antibacterial and antiprotozoal activity were analyzed. The results showed that the extracts and fractions of the leaves have a great amount of phenolic compounds, especially from the ethyl acetate fraction of leaves (FAE-F), which presented high total phenol content and flavonoids, a result that can explain the antioxidant activity evaluated by the method of DPPH (2,2-diphenyl-1-pictytoy^^yl) radical, the a-amylase enzyme inhibition and the antifungal activity for Candida glabrata. From this fraction, the flavonoid myricetin-3- O-rhamnoside was isolated and eleven phenolic compounds were identified by mass spectrometry (MS): gallic acid, (epi)-gallocatechin, methyl gallic acid derivative, ethyl gallate, myricetin-O-(O-galloyl)-hexoside, myricetin-3-O-galactoside, myricetin galloyl rhamnoside, myricetin, quercetin-3-O-rhamnoside, quercetin-3-O-(2"-galloyl)- rhamnoside and quercetin. After column fractionation of FAE-F, myricetin-3-O-acetyl- rhamnoside, digalloylquinic acid, myricetin-3-O-rhamnose-3'-O-rhamnose, trigalloylquinic acid and vanillic acid, were identified by MS. Extracts and fractions of the bark also showed a high content of phenolic compounds, such as total phenols and proanthocyanidins, especially the ethyl acetate, n-butanol and methanol fractions, which were the most active samples for inhibition of the a-amylase enzyme, antioxidant activity and antifungal activity for the Candida species tested. From the ethyl acetate fraction of the bark (FAEI-C and FAEII-C) were isolated unreported flavonoids and proanthocyanidins in the genus Inga such as 4'-O-methylgallocatechin, gallocatechin, gallocatechin-(4a-8)-4'-O-methylgalocatechin, epigallocatechin-(2—>O—>7,4—>8)-4'-O- methylgallocatechin and epigallocatechin-3-O-galoyl- (2—>O—>7,4—>8)-4'-O- methylgallocatechin. In addition, the compounds epigallocatechin-3-O-gallate, epicatechin-3-O-gallate, 4'-O-methyl-epigallocatechin-3-O-gallate, epigallocatechin-3- O-(3",4"-O-dimethyl) gallate, p-cumaric acid and prodelphinidine B-4 were identified by MS. Therefore, the I. laurina plant was characterized as a promising species as a source of biologically active phenolic compounds.FAPEMIG - Fundação de Amparo a Pesquisa do Estado de Minas GeraisTese (Doutorado)A planta Inga laurina é encontrada no cerrado brasileiro e há poucos estudos na literatura sobre esta espécie, logo, o objetivo deste trabalho foi identificar os constituintes químicos das cascas e folhas da planta. Foram analisados a atividade antioxidante, antifúngica, inibidora da enzima a-amilase, antibacteriana e antiprotozoária. Os resultados mostraram que os extratos e frações das folhas possuem grande quantidade de compostos fenólicos, especialmente a fração acetato de etila das folhas (FAE-F) que apresentou elevado teor de fenóis de totais e flavonoides, resultado que pode explicar a atividade antioxidante avaliada pelo método do radical DPPH (2,2- difenil-1-picrilidrazila), a inibição da a-amilase e a atividade antifúngica para Candida glabrata. Desta fração foi isolado o flavonoide miricetina-3-0-ramnosídeo e identificados onze compostos fenólicos por espectrometria de massas (EM): ácido gálico, (epi)galocatequina, derivado metílico do ácido gálico, galato de etila, miricetina- 0-(0-galoil)-hexosídeo, miricetina-3-0-galactosídeo, miricetina galoil ramnosídeo, miricetina, quercetina-3-0-ramnosídeo, quercetina-3-0-(2"-galoil)-ramnosídeo e quercetina. Além desses compostos foram identificados a miricetina-3-0-acetil- rammnosídeo, ácido quínico digaloil, miricetina-3-0-ramnose-3'-0-ramnosídeo, ácido quínico trigaloil e ácido vanílico nas frações da coluna. Os extratos e frações das cascas da planta também apresentaram elevado teor de compostos fenólicos, como fenóis totais e proantocianidinas, especialmente as frações acetato de etila, n-butanol e metanol, as quais foram as amostras mais ativas para a inibição da a-amilase, atividade antioxidante e atividade antifúngica para as espécies de Candida testadas. Da fração acetato de etila das cascas (FAEI-C e FAEII-C) foram isolados flavonoides e proantocianidinas inéditos no gênero Inga, 4'-0-metilgalocatequina, galocatequina, galocatequina-(4a-8)-4'-0- metilgalocatequina, epigalocatequina-(2—»-0^7,4—> 8)-4'-0-metilgalocatequina e epigalocatequina-3-0-galoil-(2—> 0^7,4—► 8)-4'-0-metilgalocatequina. Além disso, foram identificados por EM os compostos (epi)galocatequina-3-0-galato, (epi)catequina-3-0-galato, 4'-0-metil-(epi)galocatequina-3-0-galato, (epi)galocatequina-3-0-(3",4"-0-dimetil) galato, ácido ^-cumárico e prodelfinidina B- 4. Logo, a planta I. laurina foi caracterizada como uma espécie promissora como fonte de compostos fenólicos biologicamente ativos.Universidade Federal de UberlândiaBrasilPrograma de Pós-graduação em QuímicaOliveira, Alberto dehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772867Y7Morais, Sérgio Antônio Lemos dehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4785579U7Severino, Richele Priscilahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772951Y3Pivatto, Amanda Danuellohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4702249Y2Batista, Alex Domingueshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4256613E7Assunção, Rosana Maria Nascimento dehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4721828J3Martins, Carla de Moura2017-08-22T16:23:32Z2017-08-22T16:23:32Z2017-04-28info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisapplication/pdfMARTINS, Carla de Moura. Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae). 2017. 293 f. Tese (Doutorado em Química) - Universidade Federal de Uberlândia, Uberlândia, 2017. DOI http://dx.doi.org/10.14393/ufu.te.2017.97https://repositorio.ufu.br/handle/123456789/19563http://dx.doi.org/10.14393/ufu.te.2017.97porinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFUinstname:Universidade Federal de Uberlândia (UFU)instacron:UFU2019-11-06T12:53:37Zoai:repositorio.ufu.br:123456789/19563Repositório InstitucionalONGhttp://repositorio.ufu.br/oai/requestdiinf@dirbi.ufu.bropendoar:2019-11-06T12:53:37Repositório Institucional da UFU - Universidade Federal de Uberlândia (UFU)false
dc.title.none.fl_str_mv Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
title Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
spellingShingle Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
Martins, Carla de Moura
Química
Inga (Botânica) - Composição
Antioxidantes
Cerrados
Inga laurina
Antifúngico
a-Amilase
Brazilian Cerrado
Antioxidant
Antifungal
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
title_full Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
title_fullStr Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
title_full_unstemmed Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
title_sort Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
author Martins, Carla de Moura
author_facet Martins, Carla de Moura
author_role author
dc.contributor.none.fl_str_mv Oliveira, Alberto de
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772867Y7
Morais, Sérgio Antônio Lemos de
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4785579U7
Severino, Richele Priscila
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772951Y3
Pivatto, Amanda Danuello
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4702249Y2
Batista, Alex Domingues
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4256613E7
Assunção, Rosana Maria Nascimento de
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4721828J3
dc.contributor.author.fl_str_mv Martins, Carla de Moura
dc.subject.por.fl_str_mv Química
Inga (Botânica) - Composição
Antioxidantes
Cerrados
Inga laurina
Antifúngico
a-Amilase
Brazilian Cerrado
Antioxidant
Antifungal
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
topic Química
Inga (Botânica) - Composição
Antioxidantes
Cerrados
Inga laurina
Antifúngico
a-Amilase
Brazilian Cerrado
Antioxidant
Antifungal
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description The plant Inga laurina is found in Brazilian cerrado and there are few studies in the literature about this species, so the objective of this work was to identify the chemical constituents of bark and leaves that are responsible for the biological activities observed. Antioxidant activity, antifungal, a-amylase inhibitor, antibacterial and antiprotozoal activity were analyzed. The results showed that the extracts and fractions of the leaves have a great amount of phenolic compounds, especially from the ethyl acetate fraction of leaves (FAE-F), which presented high total phenol content and flavonoids, a result that can explain the antioxidant activity evaluated by the method of DPPH (2,2-diphenyl-1-pictytoy^^yl) radical, the a-amylase enzyme inhibition and the antifungal activity for Candida glabrata. From this fraction, the flavonoid myricetin-3- O-rhamnoside was isolated and eleven phenolic compounds were identified by mass spectrometry (MS): gallic acid, (epi)-gallocatechin, methyl gallic acid derivative, ethyl gallate, myricetin-O-(O-galloyl)-hexoside, myricetin-3-O-galactoside, myricetin galloyl rhamnoside, myricetin, quercetin-3-O-rhamnoside, quercetin-3-O-(2"-galloyl)- rhamnoside and quercetin. After column fractionation of FAE-F, myricetin-3-O-acetyl- rhamnoside, digalloylquinic acid, myricetin-3-O-rhamnose-3'-O-rhamnose, trigalloylquinic acid and vanillic acid, were identified by MS. Extracts and fractions of the bark also showed a high content of phenolic compounds, such as total phenols and proanthocyanidins, especially the ethyl acetate, n-butanol and methanol fractions, which were the most active samples for inhibition of the a-amylase enzyme, antioxidant activity and antifungal activity for the Candida species tested. From the ethyl acetate fraction of the bark (FAEI-C and FAEII-C) were isolated unreported flavonoids and proanthocyanidins in the genus Inga such as 4'-O-methylgallocatechin, gallocatechin, gallocatechin-(4a-8)-4'-O-methylgalocatechin, epigallocatechin-(2—>O—>7,4—>8)-4'-O- methylgallocatechin and epigallocatechin-3-O-galoyl- (2—>O—>7,4—>8)-4'-O- methylgallocatechin. In addition, the compounds epigallocatechin-3-O-gallate, epicatechin-3-O-gallate, 4'-O-methyl-epigallocatechin-3-O-gallate, epigallocatechin-3- O-(3",4"-O-dimethyl) gallate, p-cumaric acid and prodelphinidine B-4 were identified by MS. Therefore, the I. laurina plant was characterized as a promising species as a source of biologically active phenolic compounds.
publishDate 2017
dc.date.none.fl_str_mv 2017-08-22T16:23:32Z
2017-08-22T16:23:32Z
2017-04-28
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 MARTINS, Carla de Moura. Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae). 2017. 293 f. Tese (Doutorado em Química) - Universidade Federal de Uberlândia, Uberlândia, 2017. DOI http://dx.doi.org/10.14393/ufu.te.2017.97
https://repositorio.ufu.br/handle/123456789/19563
http://dx.doi.org/10.14393/ufu.te.2017.97
identifier_str_mv MARTINS, Carla de Moura. Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae). 2017. 293 f. Tese (Doutorado em Química) - Universidade Federal de Uberlândia, Uberlândia, 2017. DOI http://dx.doi.org/10.14393/ufu.te.2017.97
url https://repositorio.ufu.br/handle/123456789/19563
http://dx.doi.org/10.14393/ufu.te.2017.97
dc.language.iso.fl_str_mv por
language por
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 Federal de Uberlândia
Brasil
Programa de Pós-graduação em Química
publisher.none.fl_str_mv Universidade Federal de Uberlândia
Brasil
Programa de Pós-graduação em Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFU
instname:Universidade Federal de Uberlândia (UFU)
instacron:UFU
instname_str Universidade Federal de Uberlândia (UFU)
instacron_str UFU
institution UFU
reponame_str Repositório Institucional da UFU
collection Repositório Institucional da UFU
repository.name.fl_str_mv Repositório Institucional da UFU - Universidade Federal de Uberlândia (UFU)
repository.mail.fl_str_mv diinf@dirbi.ufu.br
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