Four new saponins have been isolated from the stem bark of Filicium decipiens and identified as 3-O-{β-D-glucopyranosyl(1 → 2)-β-D- glucopyranosyl}-28-O-{[α-L-arabinopyranosyl(1 → 2)-β-D-xylopyranosyl (1 → 6)] [4-O-angeloyloxy-α-L-arabinopyranosyl(1 → 2)-α-L-rhamnopyranosyl(1 → 2)]}-β-D-glucopyranosyl gypsogenic acid, 3-O-{β-D-glucopyranosyl(1 → 2)-β-D-glucopyranosyl}-28-O-{α-L-arabinopyranosyl(1 → 2)-β-D- xylopyranosyl(1 → 6)] [4-O-angeloyloxy-α-L-arabinopyranosyl(1 → 2)-α-L- rhamnopyranosyl(1 → 2)]}-β-D-glucopyranosyl medicagenic acid, 3-O-{β-D- glucopyranosyl(1 → 2)-β-D-glucopyranosyl}-28-O-{[α-L-ara-binopyranosyl(1 → 2)] [β-D-xylopyranosyl(1 → 4)]α-L-rhamnopyranosyl(1 → 2)-4-O-[(3'- hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D- fucopyranosyl} medicagenic acid and 3-O-β-D-glucopyranosyl-28-O-{[α-L- arabinopyranosyl(1 → 2)] [β-D-xylopyranosyl(1 → 4)] α-L- rhamnopyranosyl(1 → 2)-4-O-[(3'-hydroxy-2-methyl-butyroyloxy)-3-hydroxy-2- methyl-butyroyloxy]-β-D-fucopyranosyl} zanhic acid. These structures were elucidated by analysis of 2D-NMR spectra and of electrospray ionization mass spectra.
nilic acid, stem bark, triterpene saponins, Sapindaceae, angelic acid, Filicium decipiens
NCBI PubMed ID: 9433818Publication DOI: 10.1016/S0031-9422(97)00586-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Laboratoire de Pharmacognosie, UPRESA CNRS 6013, 51096 Reims Cedex, France, Laboratoire de Spectrometrie de Masse, ICSN, 91198 GIF/YVETTE Cedex, France, Centre de Recherche Phytochimique, Université de Liège, Sart-Tilman, Belgium, Service Central d'Analyse du CNRS, Echangeur de Solaize, Vernaison, France
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, acid hydrolysis, LSI-MS, extraction, optical rotation measurement, peracetylation, HMBC, HMQC, COSY, HOHAHA