New antimalarials with a triterpenic scaffold from Momordica balsamina.
Autor(a) principal: | |
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Data de Publicação: | 2010 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10884/1319 |
Resumo: | Bioassay-guided fractionation of the methanol extract of Momordica balsamina led to the isolation of three new cucurbitane-type triterpenoids, balsaminols C-E (1-3). Their structures were elucidated on the basis of spectroscopic methods including 2D NMR experiments (COSY, HMQC, HMBC and NOESY). Balsaminols C-E, together with ten cucurbitacins isolated from the same plant (4-13), were evaluated for their antimalarial activity against the Plasmodium falciparum chloroquine-sensitive strain 3D7 and the chloroquine-resistant clone Dd2. Most of the compounds displayed antimalarial activity. Compounds 9 and 12 revealed the highest antiplasmodial effects against both strains (IC50 values: 4.6, and 7.4 microM, 3D7, respectively; 4.0, and 8.2 microM, Dd2, respectively). Structure-activity relationships are discussed. Furthermore, the preliminary toxicity toward human cells of compounds 1-5 and 9 was investigated in breast cancer cell line (MCF-7). Compounds were inactive or showed weak toxicity (IC50 values>19.0). |
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New antimalarials with a triterpenic scaffold from Momordica balsamina.Bioassay-guided fractionation of the methanol extract of Momordica balsamina led to the isolation of three new cucurbitane-type triterpenoids, balsaminols C-E (1-3). Their structures were elucidated on the basis of spectroscopic methods including 2D NMR experiments (COSY, HMQC, HMBC and NOESY). Balsaminols C-E, together with ten cucurbitacins isolated from the same plant (4-13), were evaluated for their antimalarial activity against the Plasmodium falciparum chloroquine-sensitive strain 3D7 and the chloroquine-resistant clone Dd2. Most of the compounds displayed antimalarial activity. Compounds 9 and 12 revealed the highest antiplasmodial effects against both strains (IC50 values: 4.6, and 7.4 microM, 3D7, respectively; 4.0, and 8.2 microM, Dd2, respectively). Structure-activity relationships are discussed. Furthermore, the preliminary toxicity toward human cells of compounds 1-5 and 9 was investigated in breast cancer cell line (MCF-7). Compounds were inactive or showed weak toxicity (IC50 values>19.0).Bioorganic & Medicinal Chemistry2018-08-28T10:53:13Z2010-07-01T00:00:00Z2010-07info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10884/1319engRamalhete, CátiaLopes, DinoraMulhovo, SilvaMolnar, JosephRosário, Virgilio EstólioFerreira, Maria Joséinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-01-04T11:08:02Zoai:repositorio-cientifico.uatlantica.pt:10884/1319Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:29:53.715976Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
New antimalarials with a triterpenic scaffold from Momordica balsamina. |
title |
New antimalarials with a triterpenic scaffold from Momordica balsamina. |
spellingShingle |
New antimalarials with a triterpenic scaffold from Momordica balsamina. Ramalhete, Cátia |
title_short |
New antimalarials with a triterpenic scaffold from Momordica balsamina. |
title_full |
New antimalarials with a triterpenic scaffold from Momordica balsamina. |
title_fullStr |
New antimalarials with a triterpenic scaffold from Momordica balsamina. |
title_full_unstemmed |
New antimalarials with a triterpenic scaffold from Momordica balsamina. |
title_sort |
New antimalarials with a triterpenic scaffold from Momordica balsamina. |
author |
Ramalhete, Cátia |
author_facet |
Ramalhete, Cátia Lopes, Dinora Mulhovo, Silva Molnar, Joseph Rosário, Virgilio Estólio Ferreira, Maria José |
author_role |
author |
author2 |
Lopes, Dinora Mulhovo, Silva Molnar, Joseph Rosário, Virgilio Estólio Ferreira, Maria José |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Ramalhete, Cátia Lopes, Dinora Mulhovo, Silva Molnar, Joseph Rosário, Virgilio Estólio Ferreira, Maria José |
description |
Bioassay-guided fractionation of the methanol extract of Momordica balsamina led to the isolation of three new cucurbitane-type triterpenoids, balsaminols C-E (1-3). Their structures were elucidated on the basis of spectroscopic methods including 2D NMR experiments (COSY, HMQC, HMBC and NOESY). Balsaminols C-E, together with ten cucurbitacins isolated from the same plant (4-13), were evaluated for their antimalarial activity against the Plasmodium falciparum chloroquine-sensitive strain 3D7 and the chloroquine-resistant clone Dd2. Most of the compounds displayed antimalarial activity. Compounds 9 and 12 revealed the highest antiplasmodial effects against both strains (IC50 values: 4.6, and 7.4 microM, 3D7, respectively; 4.0, and 8.2 microM, Dd2, respectively). Structure-activity relationships are discussed. Furthermore, the preliminary toxicity toward human cells of compounds 1-5 and 9 was investigated in breast cancer cell line (MCF-7). Compounds were inactive or showed weak toxicity (IC50 values>19.0). |
publishDate |
2010 |
dc.date.none.fl_str_mv |
2010-07-01T00:00:00Z 2010-07 2018-08-28T10:53:13Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10884/1319 |
url |
http://hdl.handle.net/10884/1319 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
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 |
Bioorganic & Medicinal Chemistry |
publisher.none.fl_str_mv |
Bioorganic & Medicinal Chemistry |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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