6533b82cfe1ef96bd128fd55

RESEARCH PRODUCT

New Triterpenoidal Saponins Acylated with Monoterpenic Acid fromAlbizia adianthifolia

Tomofumi MiyamotoMohamed HaddadMarie Aleth Lacaille-dubois

subject

Inorganic Chemistrychemistry.chemical_compoundbiologyStereochemistryChemistryOrganic ChemistryDrug DiscoveryHydroxymethylPhysical and Theoretical Chemistrybiology.organism_classificationBiochemistryCatalysisAlbizia adianthifolia

description

Four new triterpenoidal saponins acylated with monoterpenic acid, i.e., adianthifoliosides C, D, E, and F (1–4), besides the two known julibroside III and the monodesmonoterpenyl elliptoside A, were isolated from the roots of Albizia adianthifolia. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry as 3-O-{O-α-L-arabinopyranosyl-(12)-O-β-d-fucopyranosyl-(16)-O-[β-d-glucopyranosyl-(12)]-β-d-glucopyranosyl}-21-O-{(2E,6S)-6-{{4-O-[(2E,6S)-2,6-dimethyl-6-(β-D-quinovopyranosyloxy)octa-2,7-dienoyl]-β-d-quinovopyranosyl}oxy}-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl}acacic acid 28-{O-α-L-arabinofuranosyl-(14)-O-[β-d-glucopyranosyl-(13)]-O-α-L-rhamnopyranosyl-(12)-β-d-glucopyranosyl} ester (1), 21-O-{(2E,6S)-6-{{4-O-[(2E,6S)-2,6-dimethyl-6-(β-d-quinovopyranosyloxy)octa-2,7-dienoyl]-β-d-quinovopyranosyl}oxy}-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl}-3-O-{O-β-D-xylopyranosyl-(12)-O-β-d-fucopyranosyl-(16)-2-(acetylamino)-2-deoxy-β-d-glucopyranosyl}acacic acid 28-{O-α-L-arabinofuranosyl-(14)-O-[β-d-glucopyranosyl-(13)]-O-α-L-rhamnopyranosyl-(12)-β-d-glucopyranosyl} ester (2), 21-O-{(2E,6S)-6-{{3-O-[(2E,6S)-2,6-dimethyl-6-(β-d-quinovopyranosyloxy)octa-2,7-dienoyl]-β-d-quinovopyranosyl}oxy}-2,6-dimethylocta-2,7-dienoyl}-3-O-{O-β-D-xylopyranosyl-(12)-O-β-d-fucopyranosyl-(16)-2-(acetylamino)-2-deoxy-β-d-glucopyranosyl}acacic acid 28-{O-α-L-arabinofuranosyl-(14)-O-[β-d-glucopyranosyl-(13)]-O-α-L-rhamnopyranosyl-(12)-β-d-glucopyranosyl} ester (3), and 3-O-{O-α-L-arabinopyranosyl-(12)-O-β-d-fucopyranosyl-(16)-O-[β-d-glucopyranosyl-(12)]-β-d-glucopyranosyl}-21-O-{(2E,6S)-2,6-dimethyl-6-(β-d-quinovopyranosyloxy)octa-2,7-dienoyl}acacic acid 28-{O-α-L-arabinofuranosyl-(14)-O-[β-d-glucopyranosyl-(13)]-O-α-L-rhamnopyranosyl-(12)-β-d-glucopyranosyl} ester (4).

https://doi.org/10.1002/hlca.200490112