Acylated flavonol tetraglycosides from Delphinium gracile

• Published in: Phytochemistry (Oxford) 2010-03, Vol.71 (4), p.463-468
• Main Authors: Diaz, Jesús G., Herz, Werner
• Format: Article
• Language: English
• Subjects: Acylated kaempferol tetraglycosides; Acylated quercetin tetraglycosides; Acylation; Biological and medical sciences; Chemical constitution; chemical structure; Delphinium; Delphinium - chemistry; Delphinium gracile; Flavonoids; flavonols; Flavonols - chemistry; Fundamental and applied biological sciences. Psychology; glycosides; Glycosides - chemistry; Glycosides - isolation & purification; kaempferol; Magnetic Resonance Spectroscopy; Plant physiology and development; quercetin; Ranunculaceae; spectral analysis
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2009.11.011

Monoacylated quercetin tetraglycosides 1– 3, the diacylated kaempferol tetraglycoside kaempferol-3- O-α- d-glucopyranosyl (1 → 3)-4- O-(E- p-coumaroyl)-α- l-rhamnopyranosyl (1 → 6)-β- d-glucopyranoside-7- O-(4- O-acetyl)-α- l-rhamnopyranoside, the latter’s 3- O-{[β- d-xylopyranosyl analog and 4-β- d-glucopyranosyloxy-6-methyl-2H-pyran-2-one were isolated from the aerial parts of Delphinium gracile DC. Structures were established by spectroscopic methods and chemical preparation of derivatives. An ethanol extract of the aerial parts of Delphinium gracile DC. yielded five flavonol glycosides quercetin-3- O-{[β- d-xylopyranosyl (1 → 3)-4- O-(E- p-caffeoyl)-α- l-rhamnopyranosyl (1 → 6)][β- d-glucopyranosyl (1 → 2)]}-β- d-glucopyranoside ( 1), quercetin-3- O-{[β- d-xylopyranosyl (1 → 3)-4- O-(E- p-coumaroyl)-α- l-rhamnopyranosyl (1 → 6)][β- d-glucopyranosyl (1 → 2)]}-β- d-glucopyranoside ( 2), quercetin-3- O-{[β- d-xylopyranosyl (1 → 3)-4- O-(Z- p-coumaroyl)-α- l-rhamnopyranosyl (1 → 6)][β- d-glucopyranosyl (1 → 2)]}-β- d-glucopyranoside ( 3), kaempferol-3- O-{[β- d-glucopyranosyl (1 → 3)-4- O-(E- p-coumaroyl)-α- l-rhamnopyranosyl (1 → 6)][β- d-glucopyranoside-7- O-(4- O-acetyl)-α- l-rhamnopyranoside ( 4) kaempferol-3- O-{[β- d-glucopyranosyl (1 → 3)-4- O-(E- p-coumaroyl)-α- l-rhamnopyranosyl (1 → 6)][β- d-glucopyranoside-7- O-(4- O-acetyl)-α- l-rhamnopyranoside ( 5) in addition to 4-(β- d-glucopyranosyloxy)-6-methyl-2H-pyran-2-one ( 6) and rutin. Structures were elucidated by spectroscopic methods.