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Inhibition of NO Production by Grindelia argentina and Isolation of Three New Cytotoxic Saponins
Author(s) -
Alza Natalia P.,
PferschyWenzig EvaMaria,
Ortmann Sabine,
Kretschmer Nadine,
Kunert Olaf,
Rechberger Gerald N.,
Bauer Rudolf,
Murray Ana P.
Publication year - 2014
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201300193
Subject(s) - chemistry , stereochemistry , cytotoxic t cell , phytochemical , cytotoxicity , asteraceae , saponin , cell culture , terpene , traditional medicine , in vitro , biochemistry , botany , biology , medicine , alternative medicine , genetics , pathology
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‐2 β ,3 β ,16 α ,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‐2 β ,3 β ,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‐2 β ,3 β ,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 ( IC 50 51.4 μ M ), while grindeliosides A–C were found to be cytotoxic, with grindelioside C being the most active against both CCRF‐CEM ( IC 50 4.2±0.1 μ M ) and MRC‐5 ( IC 50 4.5±0.1 μ M ) cell lines.