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Inhibition of NO production by Grindelia argentina and isolation of three new cytotoxic saponins.
Alza, Natalia P; Pferschy-Wenzig, Eva-Maria; Ortmann, Sabine; Kretschmer, Nadine; Kunert, Olaf; Rechberger, Gerald N; Bauer, Rudolf; Murray, Ana P.
Afiliação
  • Alza NP; INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, Bahía Blanca, 8000, Argentina (phone: +54-291-4595101 ext 3538; fax: +54-291-4595187).
Chem Biodivers ; 11(2): 311-22, 2014 Feb.
Article em En | MEDLINE | ID: mdl-24591319
A bioassay-guided phytochemical analysis of the ethanolic extract of Grindelia argentina Deble & Oliveira-Deble (Asteraceae) allowed the isolation of a known flavone, hispidulin, and three new oleanane-type saponins, 3-O-ß-D-xylopyranosyl-(1→3)-ß-D-glucopyranosyl-2ß,3ß,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-ß-D-xylopyranosyl-(1→2)-ß-D-apiofuranosyl-(1→3)-ß-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-2ß,3ß,23-trihydroxyolean-12-en-28-oic acid 28-O-ß-D-xylopyranosyl-(1→2)-ß-D-apiofuranosyl-(1→3)-ß-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl ester, (3) and 3-O-ß-D-xylopyranosyl-(1→3)-ß-D-glucopyranosyl-2ß,3ß,23-trihydroxyolean-12-en-28-oic acid 28-O-ß-D-xylopyranosyl-(1→2)-ß-D-apiofuranosyl-(1→3)-ß-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl ester (4), named grindeliosides A-C, respectively. Their structures were determined by extensive 1D- and 2D-NMR experiments along with mass spectrometry and chemical evidence. The isolated compounds were evaluated for their inhibitory activities against LPS/IFN-γ-induced NO production in RAW 264.7 macrophages and for their cytotoxic activities against the human leukemic cell line CCRF-CEM and MRC-5 lung fibroblasts. Hispidulin markedly reduced LPS/IFN-γ-induced NO production (IC50 51.4 µM), while grindeliosides A-C were found to be cytotoxic, with grindelioside C being the most active against both CCRF-CEM (IC50 4.2±0.1 µM) and MRC-5 (IC50 4.5±0.1 µM) cell lines.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Saponinas / Grindelia / Óxido Nítrico Limite: Humans País/Região como assunto: America do sul / Argentina Idioma: En Revista: Chem Biodivers Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2014 Tipo de documento: Article País de publicação: Suíça

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Saponinas / Grindelia / Óxido Nítrico Limite: Humans País/Região como assunto: America do sul / Argentina Idioma: En Revista: Chem Biodivers Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2014 Tipo de documento: Article País de publicação: Suíça