6533b821fe1ef96bd127c31f

RESEARCH PRODUCT

Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum.

Marie Aleth Lacaille-duboisGhezala GaidiMohammad RamezaniTomofumi Miyamoto

subject

StereochemistrySaponinPharmaceutical ScienceCaryophyllaceaeUronic acidIranPlant RootsAnalytical Chemistrychemistry.chemical_compoundTriterpeneDrug DiscoveryTetrasaccharideTrisaccharideNuclear Magnetic Resonance BiomolecularPharmacologychemistry.chemical_classificationPlants MedicinalMolecular StructureOrganic ChemistryGlycosideStereoisomerismSaponinsTriterpenesComplementary and alternative medicinechemistryHeteronuclear moleculeMolecular MedicineTwo-dimensional nuclear magnetic resonance spectroscopy

description

Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-3-O-acetyl-beta-D-fucopyranoside (2), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (3), and 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-[3-O-acetyl-beta-D-quinovopyranosyl-(1-->4)]-beta-D-fucopyranoside (4).

10.1021/np040001vhttps://pubmed.ncbi.nlm.nih.gov/15270563