Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium.
(3R)-O-beta-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-beta-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[beta-D-glucopyranosyl-(1-->6)-glucopyranosyl]oxy-2'-hydroxy-3', 6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-beta-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-beta-D-galactopyranoside (5), quercetin-3-O-beta-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-beta-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2''-O-galloyl)-beta-D-glucopyranoside (8), and quercetin-3-O-beta-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays.
Calis
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I
Hacettepe University, Faculty of Pharmacy, Department of Pharmacognosy, TR-061000 Ankara, Turkey. acalis@dominet.in.com.tr
Kuruüzüm
A
A
Demirezer
L O
LO
Sticher
O
O
Ganci
W
W
Rüedi
P
P
D002240:Carbohydrate Sequence; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification; D006868:Hydrolysis; D008745:Methylation; D008969:Molecular Sequence Data; D010421:Pentanoic Acids / Q000737:chemistry* / Q000302:isolation & purification; D010946:Plants, Medicinal / Q000737:chemistry*; D019664:Polygonaceae / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D014421:Turkey
D005419:Flavonoids; D006027:Glycosides; D010421:Pentanoic Acids; C400347:5-phenylvaleric acid