ABSTRACT
The protective effect of phenylpropanoid glycosides, forsythoside B and alyssonoside, and the iridoid glycoside lamiide, isolated from the aerial parts of Phlomis pungens var. pungens, against free radical-induced impairment of endothelium-dependent relaxation in isolated rat aorta was investigated. Aortic rings were exposed to free radicals by the electrolysis of the physiological bathing solution. Free radical-induced inhibition of the endothelium-dependent relaxation in response to acetylcholine was countered by incubation of the aortic rings before electrolysis with the aqueous extract (200 microg/ml), phenylpropanoid fraction (100 microg/ml) and iridoid fraction (150 microg/ml) of P. pungens var. pungens. Major components of the phenylpropanoid fraction forsythoside B and alyssonoside also prevented the inhibition of the acetylcholine response, at 10(-4) M concentration. However, the major component of iridoid fraction lamiide was found ineffective at the same concentration. The protective activity of phenylpropanoid glycosides against the free radical-induced impairment of endothelium-dependent relaxation may be related to their free radical scavenging property.
Subject(s)
Aorta, Thoracic/drug effects , Endothelium, Vascular/drug effects , Free Radical Scavengers/pharmacology , Glycosides/pharmacology , Animals , Aorta, Thoracic/physiology , Dose-Response Relationship, Drug , Drug Evaluation, Preclinical , Endothelium, Vascular/physiology , Free Radical Scavengers/antagonists & inhibitors , Glycosides/chemistry , Glycosides/isolation & purification , Lamiaceae/chemistry , Male , Phenylethyl Alcohol/chemistry , Phenylethyl Alcohol/isolation & purification , Phenylethyl Alcohol/pharmacology , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Propanols/chemistry , Propanols/isolation & purification , Propanols/pharmacology , Rats , Vasodilation/drug effects , Vasodilation/physiologyABSTRACT
Two new polyphenolic compounds, myricetin 3-O-(2"-O-galloyl)-beta-D-glucopyranoside and (-)-6-chloroepicatechin, were isolated from the aerial parts of Geranium pratense subsp. finitimum (Woronow) Knuth, along with three known polyphenolic compounds [quercetin 3-O-(2"-O-galloyl)-beta-D-glucopyranoside, quercetin 3-O-(2"-O-galloyl)-beta-D-galactopyranoside, methyl gallate] and tryptophan. Quercetin 3-O-beta-D-glucopyranoside, quercetin 3-O-beta-D-galactopyranoside, quercetin 3-O-(2"-O-galloyl)-beta-D-glucopyranoside and quercetin 3-O-(2"-O-galloyl)-beta-D-galactopyranoside were found to be effective against free radical induced impairment of endothelium-dependent relaxation in isolated rat aorta.
Subject(s)
Catechin/isolation & purification , Free Radical Scavengers/isolation & purification , Glycosides/isolation & purification , Rosales/chemistry , Animals , Catechin/analogs & derivatives , Catechin/chemistry , Catechin/pharmacology , Endothelium, Vascular/drug effects , Endothelium, Vascular/physiology , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Glycosides/chemistry , Glycosides/pharmacology , In Vitro Techniques , Male , Molecular Structure , Muscle Relaxation/drug effects , Rats , Spectrum AnalysisSubject(s)
Central Nervous System Stimulants/isolation & purification , Glycosides/isolation & purification , Plants, Medicinal , Glycosides/chemistry , Japan , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Spectrometry, Mass, Fast Atom Bombardment , Spectroscopy, Fourier Transform InfraredABSTRACT
Acteoside, a phenylpropanoid glycoside with anti-oxidative activity, induced cell death in promyelocytic leukemia HL-60 cells with an IC50 value of 26.7/microM. Analysis of extracted DNA on agarose gel electrophoresis revealed that acteoside induced the internucleosomal breakdown of chromatin DNA characteristic of apoptosis. Apoptosis-specific DNA fragmentation was clearly detectable 4 h after treatment with acteoside and was independent of the cell cycle phase. These data indicate that acteoside induces apoptosis in HL-60 cells.
Subject(s)
Antioxidants/pharmacology , Apoptosis/drug effects , Glucosides/pharmacology , Phenols , DNA Fragmentation , Electrophoresis, Agar Gel , Flow Cytometry , HL-60 Cells , Humans , Indicators and ReagentsABSTRACT
A phenylpropanoid glycoside acteoside was found to induce interleukin (IL)-1, IL-6, and tumor necrosis factor-alpha (TNF-alpha) in macrophage-like cell line J774.A1 at 1-100 ng/ml. In addition, when the stimulatory action of acteoside was studied using the bovine glomerular endothelial cell line GEN-T, it stimulated IL-6 production. These stimulatory activities were not abolished by treatment with polymixin B, which inactivates lipopolysaccharide (LPS), indicating that the action was not a contamination of LPS.
Subject(s)
Cytokines/biosynthesis , Glucosides/pharmacology , Macrophages/drug effects , Phenols , Phenylpropionates/pharmacology , Animals , Anti-Inflammatory Agents/pharmacology , Cattle , Cell Line , Dose-Response Relationship, Drug , Enzyme Inhibitors/pharmacology , Macrophages/metabolism , Mice , Tumor Necrosis Factor-alpha/biosynthesisABSTRACT
Four new minor saponins, papyrioside LE-LH, were isolated from the leaves of Tetrapanax papyriferum, and their structures were determined on the basis of spectroscopic evidence.
Subject(s)
Plant Extracts/chemistry , Saponins/chemistry , Chromatography, High Pressure Liquid , Gas Chromatography-Mass Spectrometry , Magnetic Resonance SpectroscopyABSTRACT
Four novel cycloartane-type triterpene glycosides, macrophyllosaponins A-D (1-4) were isolated from the roots of Astragalus oleifolius. By means of chemical (acetylation, alkaline hydrolysis) and spectroscopic methods (IR, 1D- and 2D-NMR, FABMS), their structures were established as 3-O-alpha-L-rhamnopyranosyl-24-O-(4"-O-acetyl)-beta-D-xylopyranosyl-1 alpha,3 beta,7 beta,24(S), 25-pentahydroxycycloartane (1), 3-O-alpha-L-rhamnopyranosyl-24-O-beta-D-xylopyranosyl-1 alpha,3 beta, 7 beta,24(S), 25-pentahydroxycycloartane (2), 3-O-alpha-L-rhamnopyranosyl-25-O-beta-D-glucoyranosyl-1 alpha, 3 beta,7 beta,24(S),25-pentahydroxycycloartane (3), and 3-O-alpha-L-rhamnopyranosyl-24-O-(2-O-beta-D-xylopyranosyl) -beta-D-xylopyranosyl-1 alpha,3 beta,7 beta,24(S), 25-pentahydroxycycloartane (4).
Subject(s)
Fabaceae/chemistry , Plants, Medicinal , Saponins/isolation & purification , Carbohydrate Sequence , Chromatography, Liquid , Hydrolysis , Magnetic Resonance Spectroscopy , Molecular Sequence Data , Plant Roots/chemistry , Saponins/chemistry , Spectrophotometry, Infrared , TurkeyABSTRACT
Four new oleanane-type saponins, papyrioside LA--LD, were isolated from the leaves of Tetrapanax papyriferum. The structures of these new compounds were elucidated as 11 alpha-hydroxy-3,21-dioxo-olean-12-en-28-oyl-alpha-L-rhamnopyranosy l- (1-->4)-(6-O-acetyl-beta-D-glucopyranosyl)-(1-->6)- beta-D-glucopyranoside, 11 alpha-methoxy-3,21-dioxo-olean-12-en-28-oyl-alpha-L-rhamnopyranosy l- (1-->4)-(6-O-acetyl-beta-D-glucopyranosyl)-(1-->6)- beta-D-glucopyranoside, 3 alpha-hydroxy-11 alpha-methoxy-21-oxo-olean-12-en-28-oyl-alpha-L-rhamnopyranosyl-(1 -->4)- (6-O-acetyl-beta-D-glucopyranosyl)-(1-->6)-beta-D-glucopyranoside and 21 alpha-hydroxy-11 alpha-methoxy-3-oxo-olean-12-en-28-oyl-alpha-L- rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)- beta-D-glucopyranoside, respectively, on the basis of spectroscopic and chemical evidence.
Subject(s)
Plant Leaves/chemistry , Saponins/isolation & purification , Terpenes/isolation & purification , Carbohydrate Sequence , Magnetic Resonance Spectroscopy , Saponins/chemistry , Spectrometry, Mass, Fast Atom Bombardment , Terpenes/chemistryABSTRACT
Ten known glycosidic compounds, betulalbuside A (1), 8-hydroxylinaloyl,3-O-beta-D-glucopyranoside (2) (monoterpen glycosides), ipolamide (3) (iridoid glycoside), acteoside (verbascoside) (4), leucosceptoside A (5), martynoside (6), forsythoside B (7), phlinoside B (8), phlinoside C (9), and teuerioside (10) (phenylpropanoid glycosides) were isolated from methanolic extracts of Phlomis armeniaca and Scutellaria salviifolia (Labiatae). Structure elucidations were carried out using 1H-, 13C-NMR and FAB-MS spectra, as well as chemical evidence. The cytotoxic and cytostatic activities of isolated compounds were investigated by the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) method. Among the glycosides obtained here, caffeic acid-containing phenylpropanoid (or phenethyl alcohol, or phenylethanoid) glycosides were found to show activity against several kinds of cancer cells. However, they didn't affect the growth and viability of primary-cultured rat hepatocytes. Study of the structure-activity relationship indicated that ortho-dihydroxy aromatic systems of phenylpropanoid glycosides are necessary for their cytotoxic and cytostatic activities.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Glycosides/pharmacology , Plants, Medicinal/chemistry , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Drug Screening Assays, Antitumor , Glycosides/chemistry , Glycosides/isolation & purification , Humans , Magnetic Resonance Spectroscopy , Mice , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Rats , Tumor Cells, Cultured , TurkeyABSTRACT
Two new phenethyl alcohol glycosides, darendoside A and B (= deacyl martynoside) were isolated from the methanolic extract of the aerial parts of Scutellaria orientalis subsp. pinnatifida, along with four known glycosides, syringin, martynoside, leucosceptoside A and verbascoside. On the basis of chemical and spectral evidence the structures of darendoside A and B were determined as beta-(4-hydroxyphenyl)ethyl O-beta-D-apiofuranosyl-(1-->2)-O-beta-D-glucopyranoside and beta-(3-hydroxy-4-methoxyphenyl)ethyl O-alpha-L-rhamnopyranosyl-(1-->3)-O-beta-D-glucopyranoside (= deacyl martynoside), respectively.
Subject(s)
Glycosides/isolation & purification , Phenols/isolation & purification , Phenylethyl Alcohol/analogs & derivatives , Phenylpropionates , Plants, Medicinal/chemistry , Carbohydrate Sequence , Glucosides/isolation & purification , Glycosides/chemistry , Molecular Sequence Data , Molecular Structure , Phenols/chemistryABSTRACT
Two new phenylpropanoid glycosides, phlinosides D and E were isolated from the methanolic extract of the aerial parts of Phlomis linearis, along with the known iridoid glucosides, lamiide, ipolamiide and auroside (= 5-hydroxy-8-epiloganin). On the basis of chemical and spectral evidence the structures of phlinosides D and E were determined as 3,4-dihydroxy-beta-phenylethoxy-O-beta-D-xylopyranosyl-(1----2)-al pha-L-rhamnopyranosyl-(1----3)-4-O-feruloyl-beta-D-glucopyranoside and 3,4-dihydroxy-beta-phenylethoxy-O-alpha-L-rhamnopyranosyl-(1----2) -alpha-L- rhamnopyranosyl-(1----3)-4-O-feruloyl-beta-D-glucopyranoside, respectively.
Subject(s)
Glycosides/isolation & purification , Acetylation , Carbohydrate Sequence , Glucosides/isolation & purification , Glycosides/chemistry , Magnetic Resonance Spectroscopy , Methylation , Molecular Sequence Data , Molecular Structure , PlantsABSTRACT
Three new phenylpropanoid glycosides, phlinosides A, B and C were isolated from a methanolic extract of the aerial parts of Phlomis linearis. On the basis of chemical and spectral evidence their structures were determined as 3,4-dihydroxy-beta-phenylethoxy-O-beta-D-glucopyranosyl-(1----2)-a lpha-L- rhamnopyranosyl-(1----3)-4-O-caffeoyl-beta-D-glucopyranoside, 3,4 dihydroxy-beta-phenylethoxy-O-beta-D-xylopyranosyl-(1----2)-alpha- L- rhamnopyranosyl-(1----3)-4-O-caffeoyl-beta-D-glucopyranoside and 3,4-dihydroxy-beta-phenylethoxy-O-alpha-L-rhamnopyranosyl-(1----2) -alpha- L-rhamnopyranosyl-(1----3)-4-O-caffeoyl-beta-D-glucopyranoside, respectively.
