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1.
Nat Prod Commun ; 4(3): 435-46, 2009 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-19413129

RESUMO

The current review outlines the distribution of flavonoids and phenolic acids in eleven species of Silphium (Asteraceae). The chemosystematic significance of these findings is discussed and compared with DNA and morphological-based assignments for eleven species. Special attention is given to the five flavonol triglycosides that were previously isolated and characterized from Silphium species: isorhamnetin 3-O-alpha-L-rhamnosyl (1""-->6")-O-beta-D-galactopyranoside 7-O-beta-L-apiofuranoside (1), quercetin 3-O-alpha-L-rhamnosyl (1"'-->6")-O-beta-D-galactopyranoside 7-O-beta-L-apiofuranoside (2), quercetin 3-O-beta-L-galactosyl (1"'-->6")-O-beta-D-rhamnopyranoside 7-O-alpha-L-apiofuranoside (3), kaempferol 3-O-beta-D-apiofuranoside 7-O-alpha-L-rhamnosyl (1""-6"')-O-beta-D-galactopyranoside (4) and kaempferol 3-O-beta-D-apiofuranoside 7-O-alpha-L-rhamnosyl (1""-->6"')-O-beta-D (2"'-O-E-caffeoylgalactopyranoside) (5). In addition, several other known mono and diglycosidic flavonoids, along with 18 phenolic acids, were also identified and the structures of all of the compounds were established by LC/MS and NMR spectral investigations.


Assuntos
Asteraceae/química , Flavonoides/análise , Hidroxibenzoatos/análise , Asteraceae/classificação , Cromatografia Líquida de Alta Pressão , Flavonoides/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Filogenia , Especificidade da Espécie
2.
Phytochemistry ; 69(4): 961-72, 2008 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-18039545

RESUMO

Nine triterpene saponins (1-9) were isolated from leaves and stems of Silphium radula Nutt. (Asteraceae). Their structures were determined by extensive 1D ((13)C, (1)H, DEPT, TOCSY) and 2D NMR (NOESY, HSQC, HMBC) and ESI-MS studies. The compounds were identified as 3beta,6beta,16beta-trihydroxyolean-12-en-23-al-3-O-beta-glucopyranosyl-16-O-beta-glucopyranoside (1), urs-12-ene-3beta,6beta,16beta-triol-3-O-beta-galactopyranosyl-(1-->2)-beta-glucopyranoside (2), 3beta,6beta,16beta-trihydroxyolean-12-en-23-oic acid-3-O-beta-glucopyranosyl-16-O-beta-glucopyranoside (3), urs-12-ene-3beta,6beta,16beta,21beta-tetraol-3-O-beta-glucopyranoside (4), olean-12-ene-3beta,6beta,16beta,21beta-tetraol-3-O-beta-glucopyranoside (5), olean-12-ene-3beta,6beta,16beta,21beta,23-pentaol-3-O-beta-glucopyranosyl-16-O-beta-glucopyranoside (6), olean-12-ene-3beta,6beta,16beta-triol-3-O-beta-glucopyranosyl-16-O-alpha-arabinopyranosyl-(1-->2)-beta-glucopyranoside (7), olean-12-ene-3beta,6beta,16beta,23-tetraol-3-O-beta-glucopyranosyl-16-O-alpha-arabinopyranosyl-(1-->2)-beta-glucopyranoside (8), 3beta,6beta,16beta,21beta-tetrahydroxyolean-12-en-23-al-3-O-beta-glucopyranoside (9). The presence of a 6beta-hydroxyl function was not common in the oleanene or ursene class and the aglycones of these compounds were not found previously in the literature. Moreover, the cytotoxic activities of the isolated compounds were tested against human breast cancer cell line MDA-MB-231. Results showed that compound 2 decreased cell proliferation in a statistically significant manner at 25 microg/ml.


Assuntos
Asteraceae/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Saponinas/química , Saponinas/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Triterpenos/química , Triterpenos/farmacologia
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