ABSTRACT
Two new naphthalene derivatives, named patientosides A (1) and B (2), were isolated from the roots of Rumex patientia. The structures of the new compounds were established as 2-acetyl-4-chloro-1,8-dihydroxy-3-methylnaphthalene-8-O-beta-D-glucopyranoside (1) and 2,4-dichloro-1,8-dihydroxy-3-methylnaphthalene-8-O-beta-D-glucopyranoside (2) by means of spectroscopic methods.
Subject(s)
Glycosides/chemistry , Naphthalenes/chemistry , Plants, Medicinal/chemistry , Polygonaceae/chemistry , Chromatography, Thin Layer , Glycosides/isolation & purification , Magnetic Resonance Spectroscopy , Naphthalenes/isolation & purification , Spectrophotometry, Ultraviolet , TurkeyABSTRACT
Three novel and two known naphthalene glycosides were isolated from the roots of Rumex patientia L. (Polygonaceae). The structures of the new compounds were established, respectively as 2-acetyl-3-methyl-6-carboxy-1,8-dihydroxynaphthalene-8-O-beta-D-glucopyranoside, 4,4"-binaphthalene-8,8"-O,O-di-beta-D-glucopyranoside and 2-acetyl-3-methyl-1,8-dihydroxynaphthalene-8-O-beta-D-glucopyranosyl (1-->3) beta-D-glucopyranoside on the basis of spectral analysis. The other napthalene glycosides were determined as nepodin-8-O-beta-D-glucopyranoside and torachrysone-8-O-beta-D-glucopyranoside by comparison of their spectral data with those previously reported.
Subject(s)
Glycosides/isolation & purification , Naphthalenes/chemistry , Plants, Medicinal/chemistry , Polygonaceae/chemistry , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Plant Roots/chemistry , TurkeyABSTRACT
In this study, the effect of an aqueous extract of Rumex patientia L. (Polygonaceae) (D-1) on capillary permeability which was induced by xylol and hyaluronidase was investigated. Experiments were conducted on rabbits according to Monakova and Matusis methods. The effects of D-1 were compared to those of indomethacin, which was used as a control throughout the experiment. Both D-1 (100 mg/kg) and indomethacin (10 mg/kg) were administered orally. As a result, D-1 inhibited capillary permeability, which was induced by xylol and hyaluronidase, and it was found that it was as effective as indomethacin.
Subject(s)
Capillary Permeability/drug effects , Hyaluronoglucosaminidase/pharmacology , Plants, Medicinal/chemistry , Polygonaceae/chemistry , Xylenes/pharmacology , Animals , Plant Extracts/pharmacology , RabbitsABSTRACT
The absolute configuration of the title compound has been determined after its enzymatic hydrolysis to 3-hydroxy-5-phenylpentanoic acid, esterification, and identification of the enantiomerically pure methyl (3R)-hydroxy-5-phenylpentanoate by HPLC on Chiralcel(R)OD-H. For reasons of inconsistent literature data, enantioselective reductions of methyl 3-oxo-5-phenylpentanoate have been reinspected and the stereochemical outcome unequivocally confirmed by both chiroptical and HPLC retention data.
Subject(s)
Glucosides/chemistry , Polygonaceae/chemistry , Chromatography, High Pressure Liquid , StereoisomerismABSTRACT
(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.
Subject(s)
Flavonoids/chemistry , Pentanoic Acids/chemistry , Plants, Medicinal/chemistry , Polygonaceae/chemistry , Carbohydrate Sequence , Flavonoids/isolation & purification , Glycosides/chemistry , Glycosides/isolation & purification , Hydrolysis , Methylation , Molecular Sequence Data , Pentanoic Acids/isolation & purification , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform Infrared , TurkeyABSTRACT
Pharmacological studies were conducted with the aqueous extract of roots of Rumex patientia L. (Polygonaceae) on experimental animals. For evaluating the antiinflammatory activity, carrageenan, histamine, dextrane, serotonine formaldehyde-induced oedema tests, cotton-pellet granuloma, and Kabak tests in rats were used. The extract was found to possess antiinflammatory activity. Acute toxicity studies revealed that the extract up to a dose of 3 mg/kg orally was nontoxic.
