Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo

Detalhes bibliográficos
Autor(a) principal: Santos,Érica L.
Data de Publicação: 2017
Outros Autores: Jo,Juliana, Marques,Francisco A., Tozzi,Ana Maria G. A., Ruiz,Ana Lúcia T. G., Maia,Beatriz Helena L. N. S.
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=S0103-50532017000801467
Resumo: Three new dibenzoylmethane derivatives, (E)-3,4-methylenedioxy-2'-methoxy-2'',2''-dimethylpyrano-(5'',6'':3',4')-7-methoxychalcone, 2'-hydroxy-5'(3'''',3''''-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane and 2'-O-(3'',3''-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane, were isolated from a dichloromethane extract from the root bark of Muellera filipes (Benth.) M.J. Silva & A.M.G. Azevedo, along with two dibenzoylmethane derivatives, 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane and 2'-hydroxy-8-(α,α-dimethylallyl)-2",2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane; one flavanone, isolonchocarpin and one flavone, pongaglabrone, which had been previously isolated from other sources. The molecular structures of the new dibenzoylmethane derivatives were determined by analysis of their spectral data (1H and 13C nuclear magnetic resonance (NMR), 2D-NMR, NOE (nuclear Overhauser effect) and HRMS (high resolution mass spectrometry). The known compounds were identified using 1D experiments and comparison with spectral data from the literature. 2'-O-(3'',3''-Dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane displayed strong activity against the human cancer cell line OVCAR-3 (ovarian), and 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane showed high selectivity for cell lines NCI-H460 (lung) and UACC-62 (melanoma).
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spelling Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. AzevedoMuellera filipesFabaceaeflavonoidsdibenzoylmethanesantiproliferative activityThree new dibenzoylmethane derivatives, (E)-3,4-methylenedioxy-2'-methoxy-2'',2''-dimethylpyrano-(5'',6'':3',4')-7-methoxychalcone, 2'-hydroxy-5'(3'''',3''''-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane and 2'-O-(3'',3''-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane, were isolated from a dichloromethane extract from the root bark of Muellera filipes (Benth.) M.J. Silva & A.M.G. Azevedo, along with two dibenzoylmethane derivatives, 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane and 2'-hydroxy-8-(α,α-dimethylallyl)-2",2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane; one flavanone, isolonchocarpin and one flavone, pongaglabrone, which had been previously isolated from other sources. The molecular structures of the new dibenzoylmethane derivatives were determined by analysis of their spectral data (1H and 13C nuclear magnetic resonance (NMR), 2D-NMR, NOE (nuclear Overhauser effect) and HRMS (high resolution mass spectrometry). The known compounds were identified using 1D experiments and comparison with spectral data from the literature. 2'-O-(3'',3''-Dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane displayed strong activity against the human cancer cell line OVCAR-3 (ovarian), and 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane showed high selectivity for cell lines NCI-H460 (lung) and UACC-62 (melanoma).Sociedade Brasileira de Química2017-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000801467Journal of the Brazilian Chemical Society v.28 n.8 2017reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20160327info:eu-repo/semantics/openAccessSantos,Érica L.Jo,JulianaMarques,Francisco A.Tozzi,Ana Maria G. A.Ruiz,Ana Lúcia T. G.Maia,Beatriz Helena L. N. S.eng2017-07-18T00:00:00Zoai:scielo:S0103-50532017000801467Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2017-07-18T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
title Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
spellingShingle Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
Santos,Érica L.
Muellera filipes
Fabaceae
flavonoids
dibenzoylmethanes
antiproliferative activity
title_short Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
title_full Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
title_fullStr Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
title_full_unstemmed Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
title_sort Antiproliferative Activity of Dibenzoylmethanes from Root Bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo
author Santos,Érica L.
author_facet Santos,Érica L.
Jo,Juliana
Marques,Francisco A.
Tozzi,Ana Maria G. A.
Ruiz,Ana Lúcia T. G.
Maia,Beatriz Helena L. N. S.
author_role author
author2 Jo,Juliana
Marques,Francisco A.
Tozzi,Ana Maria G. A.
Ruiz,Ana Lúcia T. G.
Maia,Beatriz Helena L. N. S.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Santos,Érica L.
Jo,Juliana
Marques,Francisco A.
Tozzi,Ana Maria G. A.
Ruiz,Ana Lúcia T. G.
Maia,Beatriz Helena L. N. S.
dc.subject.por.fl_str_mv Muellera filipes
Fabaceae
flavonoids
dibenzoylmethanes
antiproliferative activity
topic Muellera filipes
Fabaceae
flavonoids
dibenzoylmethanes
antiproliferative activity
description Three new dibenzoylmethane derivatives, (E)-3,4-methylenedioxy-2'-methoxy-2'',2''-dimethylpyrano-(5'',6'':3',4')-7-methoxychalcone, 2'-hydroxy-5'(3'''',3''''-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane and 2'-O-(3'',3''-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane, were isolated from a dichloromethane extract from the root bark of Muellera filipes (Benth.) M.J. Silva & A.M.G. Azevedo, along with two dibenzoylmethane derivatives, 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane and 2'-hydroxy-8-(α,α-dimethylallyl)-2",2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane; one flavanone, isolonchocarpin and one flavone, pongaglabrone, which had been previously isolated from other sources. The molecular structures of the new dibenzoylmethane derivatives were determined by analysis of their spectral data (1H and 13C nuclear magnetic resonance (NMR), 2D-NMR, NOE (nuclear Overhauser effect) and HRMS (high resolution mass spectrometry). The known compounds were identified using 1D experiments and comparison with spectral data from the literature. 2'-O-(3'',3''-Dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4'',5'':3'4')-dibenzoylmethane displayed strong activity against the human cancer cell line OVCAR-3 (ovarian), and 2'-methoxy-8-(α,α-dimethylallyl)-furano-(4'',5'':3',4')-dibenzoylmethane showed high selectivity for cell lines NCI-H460 (lung) and UACC-62 (melanoma).
publishDate 2017
dc.date.none.fl_str_mv 2017-08-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000801467
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dc.language.iso.fl_str_mv eng
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dc.relation.none.fl_str_mv 10.21577/0103-5053.20160327
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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.28 n.8 2017
reponame:Journal of the Brazilian Chemical Society (Online)
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