Inhibition of NO Production by Grindelia argentina and Isolation of Three New Cytotoxic Saponins

Authors
Alza, Natalia Paola; Pferschy Wenzig, Eva Maria; Ortmann, Sabine; Kretschmer, Nadine; Kunert, Olaf; Rechberger, Gerald N.; Bauer, Rudolf; Murray, Ana Paula
Publication Year
2014
Language
English
Format
article
Status
Published version
Description
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-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl ester (2), 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl ester, (3) and 3-O-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-apiofuranosyl-(1→3)-β-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.
Fil: Alza, Natalia Paola. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Pferschy Wenzig, Eva Maria. University of Graz; Austria
Fil: Ortmann, Sabine. University of Graz; Austria
Fil: Kretschmer, Nadine. University of Graz; Austria
Fil: Kunert, Olaf. University of Graz; Austria
Fil: Rechberger, Gerald N.. University of Graz; Austria
Fil: Bauer, Rudolf. University of Graz; Austria
Fil: Murray, Ana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Subject
GRINDELIA ARGENTINA
TRITERPENE SAPONINS
HISPIDULIN
NITRIC OXIDE
CYTOTOXICITY
Otras Ciencias Químicas
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Restricted access
License
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/30973