6533b85cfe1ef96bd12bd22d

RESEARCH PRODUCT

New Triterpene Saponins fromAcanthophyllum pachystegium

Mohammad RamezaniTomofumi MiyamotoMarie Aleth Lacaille-duboisMohamed Haddad

subject

chemistry.chemical_classificationStereochemistryOrganic ChemistryBiochemistryCatalysisInorganic ChemistryQuillaic acidTriterpenoidTriterpenechemistryHeteronuclear moleculeAcanthophyllum pachystegiumDrug DiscoveryPhysical and Theoretical ChemistryTwo-dimensional nuclear magnetic resonance spectroscopyHeteronuclear single quantum coherence spectroscopy

description

Four new triterpenoid saponins, pachystegiosides A (1), B (2), C (3), and D (4), were isolated from the roots of Acanthophyllum pachystegium K. H. Their structures were elucidated by means of a combination of homo- and heteronuclear 2D-NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FAB-MS. The new compounds were characterized as 3-O-{O-β-D-galactopyranosyl-(12)-O-[β-D-xylopyranosyl-(13)]-β-D-glucuronopyranosyl}quillaic acid 28-{O-β-D-xylopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-O-[3,4-di-O-acetyl-β-D-quinovopyranosyl-(14)]-β-D-fucopyranosyl}ester (1), 3-O-{O-β-D-galactopyranosyl-(12)-O-[β-D-xylopyranosyl-(13)]-β-D-glucuronopyranosyl}quillaic acid 28-{O-β-D-xylopyranosyl-(13)-O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-O-[4-O-acetyl-β-D-quinovopyranosyl-(14)]-β-D-fucopyranosyl} ester (2), 3-O-{O-β-D-galactopyranosyl-(12)-O-[β-D-xylopyranosyl-(13)]-β-D-glucuronopyranosyl}quillaic acid 28-{O-β-D-xylopyranosyl-(14)-O-α-L-rhamnopyranosyl-(12)-O-[4-O-acetyl-β-D-quinovopyranosyl-(14)]-β-D-fucopyranosyl} ester (3), and gypsogenic acid 28-[O-β-D-glucopyranosyl-(12)-O-β-D-glucopyranosyl-(16)-O-β-D-glucopyranosyl-(13)-β-D-galactopyranosyl] ester (4).

https://doi.org/10.1002/hlca.200490019