Acylated flavonol tetraglycosides from Delphinium gracile

An ethanol extract of the aerial parts of Delphinium gracile DC. yielded five flavonol glycosides quercetin-3-O-{[beta-d-xylopyranosyl (1-->3)-4-O-(E-p-caffeoyl)-alpha-l-rhamnopyranosyl (1-->6)][beta-d-glucopyranosyl (1-->2)]}-beta-d-glucopyranoside (1), quercetin-3-O-{[beta-d-xylopyranosyl (1-->3)-4-O-(E-p-coumaroyl)-alpha-l-rhamnopyranosyl (1-->6)][beta-d-glucopyranosyl (1-->2)]}-beta-d-glucopyranoside (2), quercetin-3-O-{[beta-d-xylopyranosyl (1-->3)-4-O-(Z-p-coumaroyl)-alpha-l-rhamnopyranosyl (1-->6)][beta-d-glucopyranosyl (1-->2)]}-beta-d-glucopyranoside (3), kaempferol-3-O-{[beta-d-glucopyranosyl (1-->3)-4-O-(E-p-coumaroyl)-alpha-l-rhamnopyranosyl (1-->6)][beta-d-glucopyranoside-7-O-(4-O-acetyl)-alpha-l-rhamnopyranoside (4) kaempferol-3-O-{[beta-d-glucopyranosyl (1-->3)-4-O-(E-p-coumaroyl)-alpha-l-rhamnopyranosyl (1-->6)][beta-d-glucopyranoside-7-O-(4-O-acetyl)-alpha-l-rhamnopyranoside (5) in addition to 4-(beta-d-glucopyranosyloxy)-6-methyl-2H-pyran-2-one (6) and rutin. Structures were elucidated by spectroscopic methods.