Five naphthalene glycosides from the roots of Rumex patientia.

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.

Antiinflammatory effect of the aqueous extract from Rumex patientia L. roots.

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.

Effect of the aqueous extract of Rumex patientia on xylol and hyaluronidase induced capillary permeability compared to indomethacin.

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.

Determination of the absolute configuration of (-)-(3R)-O-beta-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium.

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.

Two new chlorinated naphthalene glycosides from Rumex patientia.

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.

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.