Artigo

Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties

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-dim...

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Autor principal: OLIVEIRA, Dalglish Gomes de
Outros Autores: ALMEIDA, Cecília M. C. de, SILVA, Consuelo Yumiko Yoshioka e, ARRUDA, Mara Silvia Pinheiro, ARRUDA, Alberto Cardoso, LOPES, Dielly Catrina Favacho, YAMADA, Elizabeth Sumi, COSTA, Edmar Tavares da, MARTINS FILHO, Arnaldo Jorge, SILVA, Milton Nascimento da
Grau: Artigo
Idioma: eng
Publicado em: 2014
Assuntos:
Deguelia utilis
Flavonóides
Leguminosa
Timbó (planta)
Acesso em linha: http://repositorio.ufpa.br/jspui/handle/2011/5189
id ir-2011-5189
recordtype dspace
spelling ir-2011-51892018-01-02T17:26:22Z Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties OLIVEIRA, Dalglish Gomes de ALMEIDA, Cecília M. C. de SILVA, Consuelo Yumiko Yoshioka e ARRUDA, Mara Silvia Pinheiro ARRUDA, Alberto Cardoso LOPES, Dielly Catrina Favacho YAMADA, Elizabeth Sumi COSTA, Edmar Tavares da MARTINS FILHO, Arnaldo Jorge SILVA, Milton Nascimento da Deguelia utilis Flavonóides Leguminosa Timbó (planta) 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. Das folhas de Deguelia utilis foram isolados cinco flavonoides: 5,3'-di-hidróxi-4'-metóxi2'',2''-dimetilcromeno-(5'',6'':6,7)-di-hidroflavonol (1), 5,3'-di-hidróxi-7,4'-dimetóxi-6,8dimetilalil-di-hidroflavonol (2), 5,3'-di-hidróxi-4'-metóxi-8-prenil-2'',2''-dimetilcromeno(5'',6'':6,7)-flavanona (3), 5,3'-di-hidróxi-7,4'-dimetóxi-6,8-dimetilalil-flavanona (4), 3,5,3'-tri-hidróxi-7,4'-dimetóxi-6,8-dimetilalil-flavanol (5), juntamente com os estilbenos: 4-metoxilonchocarpeno (6) e lonchocarpeno (7). Suas estruturas químicas foram elucidadas com base nos seus dados de NMR (ressonância magnética nuclear) e HRESITOF-MS (espectrometria de massas de alta resolução por tempo de vôo, com ionização por eletrospray). Além disso, a fim de investigar o potencial efeito citoprotetor desses flavonoides, foi utilizada uma fração eluída com hexano:AcOEt contendo os sete flavonoides, em um modelo in vitro de neurodegeneração, utilizando culturas primárias do hipocampo de ratos neonatal (PND2-P3) expostos à rotenona, um inibidor mitocondrial do complexo I. Houve uma redução significativa da viabilidade celular (19,4 ± 1,6%), quando as culturas foram expostas à rotenona 30 nmol L-1 por 72 h. A exposição concomitante das culturas a FR3 (5 µg mL-1) e rotenona 30 nmol L-1 resultou em valores de viabilidade celular semelhante ao grupo controle (99,6 ± 4,8%), sugerindo um efeito citoprotetor para essa fração. 2014-06-30T13:39:21Z 2014-06-30T13:39:21Z 2012-10 Artigo de Periódico OLIVEIRA, Dalglish G. de et al. Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties. Journal of the Brazilian Chemical Society, São Paulo, v. 23, n. 10, p. 1933-1939, out. 2012. Disponível em: <http://www.scielo.br/pdf/jbchs/v23n10/aop094_12.pdf>. Acesso em: 21 fev. 2014. <http://dx.doi.org/10.1590/S0103-50532012005000065>. 0103-5053 http://repositorio.ufpa.br/jspui/handle/2011/5189 eng Acesso Aberto application/pdf
institution Repositório Institucional - Universidade Federal do Pará
collection RI-UFPA
language eng
topic Deguelia utilis
Flavonóides
Leguminosa
Timbó (planta)
spellingShingle Deguelia utilis
Flavonóides
Leguminosa
Timbó (planta)
OLIVEIRA, Dalglish Gomes de
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties
topic_facet Deguelia utilis
Flavonóides
Leguminosa
Timbó (planta)
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.
format Artigo
author OLIVEIRA, Dalglish Gomes de
author2 ALMEIDA, Cecília M. C. de
SILVA, Consuelo Yumiko Yoshioka e
ARRUDA, Mara Silvia Pinheiro
ARRUDA, Alberto Cardoso
LOPES, Dielly Catrina Favacho
YAMADA, Elizabeth Sumi
COSTA, Edmar Tavares da
MARTINS FILHO, Arnaldo Jorge
SILVA, Milton Nascimento da
author2Str ALMEIDA, Cecília M. C. de
SILVA, Consuelo Yumiko Yoshioka e
ARRUDA, Mara Silvia Pinheiro
ARRUDA, Alberto Cardoso
LOPES, Dielly Catrina Favacho
YAMADA, Elizabeth Sumi
COSTA, Edmar Tavares da
MARTINS FILHO, Arnaldo Jorge
SILVA, Milton Nascimento da
title Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties
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
publishDate 2014
url http://repositorio.ufpa.br/jspui/handle/2011/5189
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score 11.755432

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