Cytotoxic cordiaquinones from the roots of Cordia polycephala
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000800019 |
Resumo: | The chemical investigation of roots of Cordia polycephala resulted in the isolation of two new terpenoid naphtoquinones, 6-[10-(12,12-dimethyl-13α-(22-methyl-21-butenoyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione and (6-[10-(12,12-dimethyl-13α-(tigloyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione, named as cordiaquinone N (1) and O (2), respectively. The known cordiaquinones B (3), L (4) and E (5) were also isolated. Their structures were elucidated after detailed 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HRESIMS) data analysis. All cordiaquinones (1-5) were evaluated against four human cancer cell lines: HCT-8 (colon), HL-60 (leukemia), MDA-MB-435 (melanoma) and SF295 (glioblastoma), showing IC50 values in the range of 1.2 to 11.1 mmol L-1. The new cordiaquinones 1 and 2 were the most active against all cancer cell lines, while compound 3 was selective to leukemia HL-60 cells (IC50 2.2 mmol L-1). |
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Cytotoxic cordiaquinones from the roots of Cordia polycephalaCordia polycephalacordiaquinonescytotoxic activityThe chemical investigation of roots of Cordia polycephala resulted in the isolation of two new terpenoid naphtoquinones, 6-[10-(12,12-dimethyl-13α-(22-methyl-21-butenoyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione and (6-[10-(12,12-dimethyl-13α-(tigloyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione, named as cordiaquinone N (1) and O (2), respectively. The known cordiaquinones B (3), L (4) and E (5) were also isolated. Their structures were elucidated after detailed 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HRESIMS) data analysis. All cordiaquinones (1-5) were evaluated against four human cancer cell lines: HCT-8 (colon), HL-60 (leukemia), MDA-MB-435 (melanoma) and SF295 (glioblastoma), showing IC50 values in the range of 1.2 to 11.1 mmol L-1. The new cordiaquinones 1 and 2 were the most active against all cancer cell lines, while compound 3 was selective to leukemia HL-60 cells (IC50 2.2 mmol L-1).Sociedade Brasileira de Química2012-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000800019Journal of the Brazilian Chemical Society v.23 n.8 2012reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532012005000019info:eu-repo/semantics/openAccessFreitas,Hozana Patrícia S.Maia,Ana Isabel V.Silveira,Edilberto R.Marinho Filho,José Delano B.Moraes,Manoel O.Pessoa,CláudiaLotufo,Letícia V. CostaPessoa,Otília Deusdênia L.eng2012-09-25T00:00:00Zoai:scielo:S0103-50532012000800019Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2012-09-25T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Cytotoxic cordiaquinones from the roots of Cordia polycephala |
title |
Cytotoxic cordiaquinones from the roots of Cordia polycephala |
spellingShingle |
Cytotoxic cordiaquinones from the roots of Cordia polycephala Freitas,Hozana Patrícia S. Cordia polycephala cordiaquinones cytotoxic activity |
title_short |
Cytotoxic cordiaquinones from the roots of Cordia polycephala |
title_full |
Cytotoxic cordiaquinones from the roots of Cordia polycephala |
title_fullStr |
Cytotoxic cordiaquinones from the roots of Cordia polycephala |
title_full_unstemmed |
Cytotoxic cordiaquinones from the roots of Cordia polycephala |
title_sort |
Cytotoxic cordiaquinones from the roots of Cordia polycephala |
author |
Freitas,Hozana Patrícia S. |
author_facet |
Freitas,Hozana Patrícia S. Maia,Ana Isabel V. Silveira,Edilberto R. Marinho Filho,José Delano B. Moraes,Manoel O. Pessoa,Cláudia Lotufo,Letícia V. Costa Pessoa,Otília Deusdênia L. |
author_role |
author |
author2 |
Maia,Ana Isabel V. Silveira,Edilberto R. Marinho Filho,José Delano B. Moraes,Manoel O. Pessoa,Cláudia Lotufo,Letícia V. Costa Pessoa,Otília Deusdênia L. |
author2_role |
author author author author author author author |
dc.contributor.author.fl_str_mv |
Freitas,Hozana Patrícia S. Maia,Ana Isabel V. Silveira,Edilberto R. Marinho Filho,José Delano B. Moraes,Manoel O. Pessoa,Cláudia Lotufo,Letícia V. Costa Pessoa,Otília Deusdênia L. |
dc.subject.por.fl_str_mv |
Cordia polycephala cordiaquinones cytotoxic activity |
topic |
Cordia polycephala cordiaquinones cytotoxic activity |
description |
The chemical investigation of roots of Cordia polycephala resulted in the isolation of two new terpenoid naphtoquinones, 6-[10-(12,12-dimethyl-13α-(22-methyl-21-butenoyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione and (6-[10-(12,12-dimethyl-13α-(tigloyloxy)-16-methenylcyclohexyl)ethyl]-naphtalene-1,4-dione, named as cordiaquinone N (1) and O (2), respectively. The known cordiaquinones B (3), L (4) and E (5) were also isolated. Their structures were elucidated after detailed 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HRESIMS) data analysis. All cordiaquinones (1-5) were evaluated against four human cancer cell lines: HCT-8 (colon), HL-60 (leukemia), MDA-MB-435 (melanoma) and SF295 (glioblastoma), showing IC50 values in the range of 1.2 to 11.1 mmol L-1. The new cordiaquinones 1 and 2 were the most active against all cancer cell lines, while compound 3 was selective to leukemia HL-60 cells (IC50 2.2 mmol L-1). |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012-08-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000800019 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000800019 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532012005000019 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.23 n.8 2012 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318174058840064 |