Prospecção fitoquímica e caracterização dos compostos bioativos de Inga laurina (Sw.) Willd (Fabaceae)
Autor(a) principal: | |
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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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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) |
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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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1813711302396215296 |