Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties
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=S0103-50532012001000024 |
Resumo: | Five new flavonoids, 5,3'-dihydroxy-4'-methoxy-2'',2''-dimethylchromene-(5'',6'':6,7)dihydroflavonol (1), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-dihydroflavonol (2), 5,3'-dihydroxy-4'-methoxy-8-allyl-2'',2''-dimethylchromene-(5'',6'':6,7) flavanone (3), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-flavanone (4), 3,5,3'-trihydroxy-7,4'-dimethoxy6,8-dimethylallyl-flavanol (5), together with the stilbenes 4-methoxylonchocarpene (6) and lonchocarpene (7) were isolated from the leaves of Deguelia utilis. Their chemical structures were established on the basis of NMR (nuclear magnetic resonance) spectral data and HRESITOF-MS (electrospray ionization-high resolution time-of-flight mass spectrometry). Also, in order to investigate potential cytoprotective effects of these flavonoids, we used a fraction eluted with hexane:EtOAc containing all seven flavonoids, in an in vitro model of neurodegeneration, using hippocampal primary cultures from neonatal (PND2-P3) rats exposed to rotenone, a mitochondrial complex I inhibitor. There was a significant reduction in cell viability (19.4 ± 1.6%) when the cultures were exposed to 30 nmol L-1 rotenone for 72 h. Concomitant exposure of the cultures to the FR3 (5 µg mL-1) and 30 nmol L-1 rotenone resulted in values of cell viability similar to control groups (99.6 ± 4.8%), strongly suggesting a cytoprotective effect for this flavonoid-rich fraction. |
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Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective propertiesDeguelia utilisflavonoidsleguminosaetimbóFive new flavonoids, 5,3'-dihydroxy-4'-methoxy-2'',2''-dimethylchromene-(5'',6'':6,7)dihydroflavonol (1), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-dihydroflavonol (2), 5,3'-dihydroxy-4'-methoxy-8-allyl-2'',2''-dimethylchromene-(5'',6'':6,7) flavanone (3), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-flavanone (4), 3,5,3'-trihydroxy-7,4'-dimethoxy6,8-dimethylallyl-flavanol (5), together with the stilbenes 4-methoxylonchocarpene (6) and lonchocarpene (7) were isolated from the leaves of Deguelia utilis. Their chemical structures were established on the basis of NMR (nuclear magnetic resonance) spectral data and HRESITOF-MS (electrospray ionization-high resolution time-of-flight mass spectrometry). Also, in order to investigate potential cytoprotective effects of these flavonoids, we used a fraction eluted with hexane:EtOAc containing all seven flavonoids, in an in vitro model of neurodegeneration, using hippocampal primary cultures from neonatal (PND2-P3) rats exposed to rotenone, a mitochondrial complex I inhibitor. There was a significant reduction in cell viability (19.4 ± 1.6%) when the cultures were exposed to 30 nmol L-1 rotenone for 72 h. Concomitant exposure of the cultures to the FR3 (5 µg mL-1) and 30 nmol L-1 rotenone resulted in values of cell viability similar to control groups (99.6 ± 4.8%), strongly suggesting a cytoprotective effect for this flavonoid-rich fraction.Sociedade Brasileira de Química2012-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012001000024Journal of the Brazilian Chemical Society v.23 n.10 2012reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532012005000065info:eu-repo/semantics/openAccessOliveira,Dalglish G. deAlmeida,Cecília M. C. deSilva,Consuelo Y. Y. eArruda,Mara S. P.Arruda,Alberto C.Lopes,Dielly C. F.Yamada,Elizabeth S.Costa,Edmar T. daM. Filho,Arnaldo JorgeSilva,Milton N. daeng2013-01-07T00:00:00Zoai:scielo:S0103-50532012001000024Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2013-01-07T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties |
title |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties |
spellingShingle |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties Oliveira,Dalglish G. de Deguelia utilis flavonoids leguminosae timbó |
title_short |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties |
title_full |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties |
title_fullStr |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties |
title_full_unstemmed |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties |
title_sort |
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties |
author |
Oliveira,Dalglish G. de |
author_facet |
Oliveira,Dalglish G. de Almeida,Cecília M. C. de Silva,Consuelo Y. Y. e Arruda,Mara S. P. Arruda,Alberto C. Lopes,Dielly C. F. Yamada,Elizabeth S. Costa,Edmar T. da M. Filho,Arnaldo Jorge Silva,Milton N. da |
author_role |
author |
author2 |
Almeida,Cecília M. C. de Silva,Consuelo Y. Y. e Arruda,Mara S. P. Arruda,Alberto C. Lopes,Dielly C. F. Yamada,Elizabeth S. Costa,Edmar T. da M. Filho,Arnaldo Jorge Silva,Milton N. da |
author2_role |
author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Oliveira,Dalglish G. de Almeida,Cecília M. C. de Silva,Consuelo Y. Y. e Arruda,Mara S. P. Arruda,Alberto C. Lopes,Dielly C. F. Yamada,Elizabeth S. Costa,Edmar T. da M. Filho,Arnaldo Jorge Silva,Milton N. da |
dc.subject.por.fl_str_mv |
Deguelia utilis flavonoids leguminosae timbó |
topic |
Deguelia utilis flavonoids leguminosae timbó |
description |
Five new flavonoids, 5,3'-dihydroxy-4'-methoxy-2'',2''-dimethylchromene-(5'',6'':6,7)dihydroflavonol (1), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-dihydroflavonol (2), 5,3'-dihydroxy-4'-methoxy-8-allyl-2'',2''-dimethylchromene-(5'',6'':6,7) flavanone (3), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-flavanone (4), 3,5,3'-trihydroxy-7,4'-dimethoxy6,8-dimethylallyl-flavanol (5), together with the stilbenes 4-methoxylonchocarpene (6) and lonchocarpene (7) were isolated from the leaves of Deguelia utilis. Their chemical structures were established on the basis of NMR (nuclear magnetic resonance) spectral data and HRESITOF-MS (electrospray ionization-high resolution time-of-flight mass spectrometry). Also, in order to investigate potential cytoprotective effects of these flavonoids, we used a fraction eluted with hexane:EtOAc containing all seven flavonoids, in an in vitro model of neurodegeneration, using hippocampal primary cultures from neonatal (PND2-P3) rats exposed to rotenone, a mitochondrial complex I inhibitor. There was a significant reduction in cell viability (19.4 ± 1.6%) when the cultures were exposed to 30 nmol L-1 rotenone for 72 h. Concomitant exposure of the cultures to the FR3 (5 µg mL-1) and 30 nmol L-1 rotenone resulted in values of cell viability similar to control groups (99.6 ± 4.8%), strongly suggesting a cytoprotective effect for this flavonoid-rich fraction. |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012-10-01 |
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=S0103-50532012001000024 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012001000024 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532012005000065 |
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.10 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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1750318174393335808 |