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Two new 15-deoxycimigenol-type (1, 2) and three new 24-epi-cimigenol-type glycosides (3-5) were isolated from Cimicifuga Rhizome, and the structures were elucidated on the basis of spectroscopic data including 2D NMR spectra and chemical evidence. The two new 15-deoxycimigenol-type glycosides were the first cimigenol-type glycosides lacking a hydroxyl group at C-15.
From the unripe fruits of Lo Han Kuo (Siraitia grosvenori), a Chinese medicinal plant, two new cucurbitane triterpene glycosides, 20-hydroxy-11-oxomogroside IA(1) (1) and 11-oxomogroside IIE (2), were isolated along with five known cucurbitane glycosides, 11-oxomogroside IA(1) (3), mogroside IIE (4), mogroside III (5), mogroside IVA (6), and mogroside V (7), and two flavonoid glycosides, kaempferol 7-O-alpha-L-rhamnopyranoside (8) and kaempferol 3,7-di-O-alpha-L-rhamnopyranoside (9). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods and by comparing with literature values. This paper describes the first investigation of unripe bitter Lo Han Kuo fruits.
A new steroidal glycoside has been isolated from the underground parts of Solanum sodomaeum L., along with seven known steroidal glycosides. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence, and the structure of one known pregnane type glycoside was corrected. In addition, their antiproliferative activity against human promyelocytic leukemia (HL-60) cells was investigated, and five compounds exhibited stronger activity than cisplatin.
Three new spirostanol glycosides (1-3) and a new furostanol glycoside (4), together with two known spirostanol glycosides (5 and 6) were isolated from the whole plants of Agave utahensis (Agavaceae). The structures of the new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage.
Identification of flavonoids and flavonoid glycosides was carried out on Psidium guajava Linn leaves by means of high-performance liquid chromatography ultraviolet (HPLC-UV) analysis and HPLC mass spectrometry. By using HPLC-UV, two known phenolics (gallic acid and quercetin) and five newly reported ones (procatechuic acid, chlorogenic acid, caffeic acid, kaempferol and ferulic acid) were identified in alcohol guava leaf extract. Structural information about the compounds was obtained from the retention times, the UV spectra and mass spectra without the need to isolate the individual compounds. Two flavonoids (quercetin and kaempferol) and four flavonoid glycosides (three known components, quercetin 3-O-alpha-L-arabinoside, quercetin 3-O-beta-D-glucoside and quercetin 3-O-beta-D-galactoside, along with one novel compound, kaempferol-glycoside) and three other unknown compounds have been identified in the fractions.
A novel flavonol glycoside named camellianoside and three known flavonol glycosides were isolated from the leaves of Camellia japonica. The structure of camellianoside was established as quercetin-3-O-beta-D-xylopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->6)-O-beta-D-glucopyranoside by spectroscopic and chemical methods. The antioxidant activities of these glycosides evaluated by the diphenylpicrylhydrazyl (DPPH) radical scavenging reaction was higher than those of L-cysteine and L-ascorbic acid used as the reference antioxidants.
Glycosides were screened for their lowering effect on the postprandial blood glucose rise in vivo. The effect of phlorizin and other phenolic glycosides on the postprandial blood glucose response to glucose ingestion was evaluated in Std ddY mice. When phlorizin was simultaneously added, the peak blood glucose level was significantly decreased by 51% (p < 0.01) compared to vehicles following glucose ingestion by mice, while the blood insulin responses were generally similar. Screening experiments were conducted with different classes of phenolic glycosides added to a glucose solution. Reductions of 40-52% (p < 0.05) were observed in vehicles containing arbutin, 4-hydroxyphenyl-alpha-D-glucopyranoside (hydroquinone-alpha-glucoside) or glycyrrhizin, and of only 15-31% (not significant) in vehicles containing neohesperidin dihydrochalcone, glycyrrhetinic acid monoglucuronide, or 3,4-dimethoxyphenyl-beta-D-glucopyranoside. No lowering effect was observed in vehicles containing salicin. Since glycyrrhizin, arbutin, and hydroquinone-alpha-glucoside blunted to varying degrees the postprandial blood glucose rise following glucose ingestion, they may be useful adjuvants for the treatment of diabetic subjects.
In our screening program for antioxidants from traditional drugs and foodstuffs, one new phenylpropanoid glycoside, incanoside, was isolated together with four known phenylpropanoid glycosides, verbascoside, isoverbascoside, phlinoside A, and 6-O-caffeoyl-beta-D-glucose from the whole plant of Caryopteris incana (Thunb.) Miq. On the basis of chemical evidence and spectral analysis data, the structure of incanoside was determined to be 1-O-(3,4-dihydroxyphenyl)ethyl-O-beta-D-glucopyranosyl (1-->2)-alpha-L-rhamnopyranosyl(1-->3)-6-O-caffeoyl-beta-D- glucopyranoside. The four phenylpropanoid glycosides exhibited potent radical scavenging activity against DPPH, hydroxyl (.OH), and superoxide anion (O2-.) radicals.
A glycosidic flavonoids-rich fraction from green tea leaves was purified to isolate five glycosidic flavonoids, guided by the detection of a preventive effect on D-galactosamine-induced liver injury in rats. These were identified as a flavone C-glycoside (1) and trisaccharide flavonols (2-5) based on the spectroscopic analyses. These compounds suppressed the D-galactosamine-induced increase of plasma alanine aminotransferase and asparatate aminotransferase activities in rats.
BACKGROUND: Despite a long history of use in the treatment of paroxysmal atrial fibrillation (AF), the efficacy of cardiac glycosides has not been established. If such drugs are beneficial in this condition, the general view is that the benefit must be related to their inotropic actions. METHODS AND RESULTS: To assess the effects of the rapid-acting cardiac glycoside, acetylstrophanthidin (AS), on AF and AF-induced right atrial (RA) "stunning," RA wall motion (with ultrasonic crystals), RA pressure, and peak first derivative of pressure (dp/dt) (with microtip transducers) were measured before and after 5 min of high-intensity rapid atrial stimulation (10 Hz; 10 mA; 1 ms) and after the cessation of poststimulation AF. Measurements were made in neurally intact and autonomically blockaded dogs both before and after the administration of AS (0.01 mg/kg IV bolus and 0.015 mg/kg/h IV infusion). AS prevented the post-AF reduction in RA peak dp/dt under neurally intact and autonomically blockaded conditions, and it prevented the post-AF increase in the RA end-systolic dimension and the decrease in the percentage of RA systolic shortening with autonomic blockade. AS was beneficial whether or not baseline inotropy was enhanced by AS. The duration of AF following atrial stimulation was the same before and after AS, but when compared to controls, AS treatment appeared to prolong AF. CONCLUSIONS: Cardiac glycosides exert a favorable effect on AF-induced RA stunning, but this action is unrelated to its effects on the duration of AF.
Two new lignan glycosides of dibenzylbutyrolactol type (haplomarin) and arylnaphthalene type (haploborin) were isolated from the aerial parts of Haplophyllumn suaveolens together with the known arylnaphthalene lignan glycoside arabelline and hydroxycoumarin glycoside xeroboside. So far arabelline is found only in H. buxbaunii. This is the first report of the isolation of xeroboside from Haplophyllum.
Four novel nitrogen-free glycosides of platenolides I and II were isolated as secondary shunt metabolites of the turimycin biosynthesis from the culture broth of an industrial strain of Streptomyces hygroscopicus IMET JA 6599. By spectral (MS, 1H and 13C NMR) studies the structures of the glycosides have been settled as 5-O-(4',6'-dideoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide I (DDAH-Pl-I), 5-O-(4',6'-dideoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide II (DDAH-Pl-II), 5-O-(4',6'-dideoxy-3'-C-acetyl-beta-D-hexopyranosyl)-14-hydroxyl-platenolide II (DDAH-OH-Pl-II) and 5-O-(6'-deoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide II (DAH-Pl-II). A fifth glycoside, 5-O-(6'-deoxy-3'-C-acetyl-beta-D-hexopyranosyl)-platenolide I (DAH-Pl-I) was identified through its MS data.
Intestinal infarction in the absence of organic vascular occlusion received increasing attention in recent years. There is strong evidence from experimental work and clinical observations that cardiac glycosides may play an important role in the pathophysiology of this disorder. Our experiments using the so called mechanical ventricular massage confirm this theory. We could demonstrate that the decrease in mesenteric arterial perfusion following the i.v. administration of ouabain is caused by extracardiac effects of the glycoside on vascular smooth muscle. The Ca++ -antagonistic compound (Verapamil) blocks and reverses the Ca++-synergistic action of the glycoside independent of the time of injection.
Effects of three cardiac glycosides on the accumulation of 3H-1-noradrenaline (3H-1-NA) by slices of heart and spleen were studied. Ouabain, digitoxin and digoxin, all produced a concentration dependent inhibition of 3H-1-NA uptake in both types of tissue slices. The maximum amount of 3H-1-NA accumulated as well as the rate of uptake was decreased. Digitoxin and ouabain were equipotent; however, digoxin was significantly less potent. Tissues from different mamalian specis did not exhibit the same degree of sensitivity to the inhibitory effect of cardiac glycosides on 3H-1-NA accumulation. Dogs were most sensitive and guinea-pigs an order of magnitude less sensitive. Rats were least sensitive by roughly two orders of magnitude when compared with guinea-pigs. The relationship of the effect of digitalis on 3H-1-NA accumulation to digitalis-induced cardiac arrhythmias is discussed. Finally, the pattern of species sensitivity found here is compared with that observed in relation to inhibition of Na+-K+-ATPase by cardiac glycosides.
Two spectrophotometric methods (conventional and differential) are carried out for the estimation of flavone glycosides (hyperoside and/or kaempferol-3-beta-glucoside) in Euphorbia paralias L., and Euphorbia helioscopia L. The glycosides are extracted with methanol from the aerial parts of the different Euphorbia species, separated on silica gel chromatoplates, and eluted by refluxing with methanol (80%). The absorbance value (conventional method) and the delta absorbance value (differential method) of the prepared glycosidal solutions are measured. The results of both methods are of conveinent reproducibility.
Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and naphthyl-2 beta-glycosides, novel muramyl dipeptide derivatives with phenolic aglycones, was reported. The starting N-glucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha-glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta-glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the target glycopeptides.
OBJECTIVE: To determine the contents of four lignan glycosides in the root of Gaultheria yunnanensis, namely, D1: gaultheroside A, D2:(-)-8'-methoxyisolariciresinol-2a-O-beta-D-xylopyranoside, D3:(-)-isolariciresinol-2a-O-beta-D-xylopyranside, D4:(+)-lyoniresinol-2a-O-beta-D-glucoxylopyranoside. METHOD: Rp-HPLC was used to separate and analyze the lignan glycosides in the root of the title plant. RESULT: The method for sample preparation was set up; the gradient program for the mobile phase was established; and the retention times of four lignan glycosides were determined. CONCLUSION: The method has been proved to be accurate, reproducible and of higher recovery rate.
Features specific for the action produced by the most widely employed cardiac glycosides (strophanthin, corglycon, proscillardin A, methyl- and acetyldigoxine, isolanide, digoxine and digitoxin) on the hemodynamics, peripheral resistance, electrolyte composition, acid-base equilibrium, the blood adenyl system, etc were studied in 375 patients with different stages of chronic circulatory insufficiency. The data thus made available allowed some suggestions to be made as to the choice of cardiac glycosides, the duration of their application, possible combinations thereof, and also to propose a number of measures aimed at preventing the development of poisoning with cardiac glycosides.