Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana

Detalhes bibliográficos
Autor(a) principal: Leticia Hiromi Ohashi
Data de Publicação: 2021
Outros Autores: Douglas da Costa Gontijo, Maria Fernanda Alves do Nascimento, Luciano Ferreira Margalho, Geraldo Célio Brandão, Alaíde Braga de Oliveira
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFMG
Texto Completo: https://doi.org/10.1055/a-1375-6456
http://hdl.handle.net/1843/61284
Resumo: The present study on Palicourea hoffmannseggiana, which was collected at Marapanim, state of Pará, Brazil, comprises the preparation of different stem and leaf extracts and fractions. Ethanol, hydroethanol, and water extracts were prepared by several methods and evaluated for in vitro activity against resistant Plasmodium falciparum (W2 strain), disclosing a low parasite growth inhibition effect (< 50%). Dereplication by UPLC-DAD-ESI−MS of the leaf ethanol extract showed the presence of two known alkaloids, lyalosidic and strictosidinic acids, along with a sinapoyl ester of lyalosidic acid, with m/z 719.33 [M+H]+, which is possibly a new monoterpene indole alkaloid representative. Sequential liquid-liquid acid-base alkaloid separations from the leaf ethanol extract as well as directly from leaf powder afforded fractions of increased parasite growth inhibition, reaching up to 92.5±0.7%. The most bioactive fractions were shown to contain the β-carboline alkaloids harmane and 4-methyl-β-carboline, along with N-methyl-tryptamine and N-acetyl-tryptamine, while monoterpene indole alkaloids were detected in inactive fractions of these processes. The present results demonstrate that these preliminary fractionation methods can lead to significantly active fractions supporting an adequate scale-up to carrying out the isolation of anti-plasmodial compounds.
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spelling 2023-11-22T20:51:54Z2023-11-22T20:51:54Z2021-04813442https://doi.org/10.1055/a-1375-64562509-9264http://hdl.handle.net/1843/61284The present study on Palicourea hoffmannseggiana, which was collected at Marapanim, state of Pará, Brazil, comprises the preparation of different stem and leaf extracts and fractions. Ethanol, hydroethanol, and water extracts were prepared by several methods and evaluated for in vitro activity against resistant Plasmodium falciparum (W2 strain), disclosing a low parasite growth inhibition effect (< 50%). Dereplication by UPLC-DAD-ESI−MS of the leaf ethanol extract showed the presence of two known alkaloids, lyalosidic and strictosidinic acids, along with a sinapoyl ester of lyalosidic acid, with m/z 719.33 [M+H]+, which is possibly a new monoterpene indole alkaloid representative. Sequential liquid-liquid acid-base alkaloid separations from the leaf ethanol extract as well as directly from leaf powder afforded fractions of increased parasite growth inhibition, reaching up to 92.5±0.7%. The most bioactive fractions were shown to contain the β-carboline alkaloids harmane and 4-methyl-β-carboline, along with N-methyl-tryptamine and N-acetyl-tryptamine, while monoterpene indole alkaloids were detected in inactive fractions of these processes. The present results demonstrate that these preliminary fractionation methods can lead to significantly active fractions supporting an adequate scale-up to carrying out the isolation of anti-plasmodial compounds.O presente estudo com Palicourea hoffmannseggiana, coletada em Marapanim, estado do Pará, Brasil, compreende a preparação de diferentes extratos e frações de caule e folhas. Extratos de etanol, hidroetanol e água foram preparados por vários métodos e avaliados quanto à atividade in vitro contra Plasmodium falciparum resistente (cepa W2), revelando um baixo efeito de inibição do crescimento do parasita (<50%). A desreplicação por UPLC-DAD-ESI-MS do extrato etanólico da folha mostrou a presença de dois alcalóides conhecidos, ácidos lialosídico e estritosidínico, juntamente com um éster sinapoílico de ácido lialosídico, com m/z 719,33 [M+H]+, que é possivelmente um novo representante do alcalóide indol monoterpeno. Separações sequenciais de alcalóides ácido-base líquido-líquido do extrato etanólico da folha, bem como diretamente do pó da folha, proporcionaram frações de maior inibição do crescimento do parasita, atingindo até 92,5±0,7%. Demonstrou-se que as frações mais bioativas continham os alcalóides β-carbolina harmano e 4-metil-β-carbolina, juntamente com N-metil-triptamina e N-acetil-triptamina, enquanto alcalóides indólicos monoterpênicos foram detectados em frações inativas desses processos. Os presentes resultados demonstram que estes métodos preliminares de fracionamento podem levar a frações significativamente ativas, apoiando um aumento de escala adequado para realizar o isolamento de compostos antiplasmodiais.CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorengUniversidade Federal de Minas GeraisUFMGBrasilFAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOSPlanta Medica International OpenRubiaceaePlasmodium falciparumMaláriaAntimaláricosPalicourea hoffmannseggianaRubiaceaeMonoterpene indole alkaloidsβ-carboline alkaloidsPlasmodium falciparumExtraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggianainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://www.thieme-connect.com/products/ejournals/abstract/10.1055/a-1375-6456Leticia Hiromi OhashiDouglas da Costa GontijoMaria Fernanda Alves do NascimentoLuciano Ferreira MargalhoGeraldo Célio BrandãoAlaíde Braga de Oliveiraapplication/pdfinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGLICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/61284/1/License.txtfa505098d172de0bc8864fc1287ffe22MD51ORIGINALExtraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana.pdfExtraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana.pdfapplication/pdf426965https://repositorio.ufmg.br/bitstream/1843/61284/2/Extraction%20and%20fractionation%20effects%20on%20antiplasmodial%20activity%20and%20phytochemical%20composition%20of%20Palicourea%20hoffmannseggiana.pdf852d79bbcff017ebc698076af028d66eMD521843/612842023-11-22 18:26:45.589oai:repositorio.ufmg.br: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Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2023-11-22T21:26:45Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false
dc.title.pt_BR.fl_str_mv Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
title Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
spellingShingle Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
Leticia Hiromi Ohashi
Palicourea hoffmannseggiana
Rubiaceae
Monoterpene indole alkaloids
β-carboline alkaloids
Plasmodium falciparum
Rubiaceae
Plasmodium falciparum
Malária
Antimaláricos
title_short Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
title_full Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
title_fullStr Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
title_full_unstemmed Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
title_sort Extraction and fractionation effects on antiplasmodial activity and phytochemical composition of Palicourea hoffmannseggiana
author Leticia Hiromi Ohashi
author_facet Leticia Hiromi Ohashi
Douglas da Costa Gontijo
Maria Fernanda Alves do Nascimento
Luciano Ferreira Margalho
Geraldo Célio Brandão
Alaíde Braga de Oliveira
author_role author
author2 Douglas da Costa Gontijo
Maria Fernanda Alves do Nascimento
Luciano Ferreira Margalho
Geraldo Célio Brandão
Alaíde Braga de Oliveira
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Leticia Hiromi Ohashi
Douglas da Costa Gontijo
Maria Fernanda Alves do Nascimento
Luciano Ferreira Margalho
Geraldo Célio Brandão
Alaíde Braga de Oliveira
dc.subject.por.fl_str_mv Palicourea hoffmannseggiana
Rubiaceae
Monoterpene indole alkaloids
β-carboline alkaloids
Plasmodium falciparum
topic Palicourea hoffmannseggiana
Rubiaceae
Monoterpene indole alkaloids
β-carboline alkaloids
Plasmodium falciparum
Rubiaceae
Plasmodium falciparum
Malária
Antimaláricos
dc.subject.other.pt_BR.fl_str_mv Rubiaceae
Plasmodium falciparum
Malária
Antimaláricos
description The present study on Palicourea hoffmannseggiana, which was collected at Marapanim, state of Pará, Brazil, comprises the preparation of different stem and leaf extracts and fractions. Ethanol, hydroethanol, and water extracts were prepared by several methods and evaluated for in vitro activity against resistant Plasmodium falciparum (W2 strain), disclosing a low parasite growth inhibition effect (< 50%). Dereplication by UPLC-DAD-ESI−MS of the leaf ethanol extract showed the presence of two known alkaloids, lyalosidic and strictosidinic acids, along with a sinapoyl ester of lyalosidic acid, with m/z 719.33 [M+H]+, which is possibly a new monoterpene indole alkaloid representative. Sequential liquid-liquid acid-base alkaloid separations from the leaf ethanol extract as well as directly from leaf powder afforded fractions of increased parasite growth inhibition, reaching up to 92.5±0.7%. The most bioactive fractions were shown to contain the β-carboline alkaloids harmane and 4-methyl-β-carboline, along with N-methyl-tryptamine and N-acetyl-tryptamine, while monoterpene indole alkaloids were detected in inactive fractions of these processes. The present results demonstrate that these preliminary fractionation methods can lead to significantly active fractions supporting an adequate scale-up to carrying out the isolation of anti-plasmodial compounds.
publishDate 2021
dc.date.issued.fl_str_mv 2021-04
dc.date.accessioned.fl_str_mv 2023-11-22T20:51:54Z
dc.date.available.fl_str_mv 2023-11-22T20:51:54Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1843/61284
dc.identifier.doi.pt_BR.fl_str_mv https://doi.org/10.1055/a-1375-6456
dc.identifier.issn.pt_BR.fl_str_mv 2509-9264
url https://doi.org/10.1055/a-1375-6456
http://hdl.handle.net/1843/61284
identifier_str_mv 2509-9264
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartof.none.fl_str_mv Planta Medica International Open
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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dc.publisher.none.fl_str_mv Universidade Federal de Minas Gerais
dc.publisher.initials.fl_str_mv UFMG
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv FAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOS
publisher.none.fl_str_mv Universidade Federal de Minas Gerais
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFMG
instname:Universidade Federal de Minas Gerais (UFMG)
instacron:UFMG
instname_str Universidade Federal de Minas Gerais (UFMG)
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institution UFMG
reponame_str Repositório Institucional da UFMG
collection Repositório Institucional da UFMG
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