Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
NCBI PubMed ID: 10479312Publication DOI: 10.1021/np9900674Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Calis I <acalis
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Institutions: Hacettepe University, Faculty of Pharmacy, Department of Pharmacognosy, TR-061000 Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zurich, Department of Pharmacy, CH-8057 Zurich, Switzerland, University of Zurich, Institute of Organic Chemistry, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland
(3R)-O-β-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-β-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[β-D-glucopyranosyl-(1→-6)-glucopyranosyl]-oxy-2'-hydroxy-3',6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-β-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-β-D-galactopyranoside (5), quercetin-3-O-β-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-β-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2'-O-galloyl)-β-D-glucopyranoside (8), and quercetin-3-O-β-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.
isoquercitrin, hyperoside, flavonoid glycoside, phenylvaleric acid glycoside, Polygonum salicifolium, astragalin
Structure type: monomer
Location inside paper: compound 6, chart 1(6)
Trivial name: isoquercitrin
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, TLC, enzymatic hydrolysis, ESI-MS, HPLC, UV, optical rotation measurement, ROESY, reduction with NaBH4, antioxidant activities, HMBC, HMQC, DEPT, COSY, MPLC, hydrogenation, DFQ-COSY
Biological activity: Compound 6 showed DPPH redical scavenging activity in TLC bioassay.
Comments, role: compound was identified by comparison with NMR data with rhose reported in ref. [20]
Related record ID(s): 63323, 63324, 63325, 63326, 63327, 63328, 63330, 63331, 63332
NCBI Taxonomy refs (TaxIDs): 580470Reference(s) to other database(s): CCSD:
49965, CBank-STR:953
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There is only one chemically distinct structure:
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(later renamed to: Persicaria decipiens)