Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “GLYCOSIDES”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 1,603 records · Page 89Linked to original sources
PubMed1985

New anthracycline glycosides obtained by the nitrous acid deamination of daunorubicin, doxorubicin and their configurational analogues.

The new anthracyclines 7-O-(2,3,5-trideoxy-3-C-formyl-alpha-L-threo-pentofuranosyl)daunomyci none (8) and -adriamycinone (10) have been obtained upon nitrous acid deamination of daunorubicin and doxorubicin respectively. Deamination of the L-ribo analogue of daunorubicin (6) gave a mixture of 2,3,6-trideoxy-L-glycero-hexopyranosid-4-ulose (alpha-L-cinerulosyl) (11) and 2,6-dideoxy-alpha-L-arabino-hexopyranosyl (12) glycosides. The corresponding adriamycinone glycosides 13 and 14, obtained by deamination of the doxorubicin L-ribo analogue 7, were found to display an outstanding antileukemic activity in mice.

Animals↗
PubMed1993

Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine.

Daunosamine, as its 4-O-acetyl-3-N-trifluoroacetyl glycosyl chloride derivative (1b), has been coupled alpha-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyiodination-tributylstannane reduction has been evaluated. The sequence successfully demonstrated with the methyl glycosides was successfully extended with daunomycinone as the aglycon, providing a preparative route to 7-O-[3-O-(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)- 2,6-dideoxy-alpha-L-arabino-hexopyranosyl]daunomycinone hydrochloride (15), an analogue of natural anthracycline antibiotics containing daunosamine and a 2,6-dideoxy-L-hexose.

Aminoglycosides↗
PubMed1976

[Case report on the problem of individual glycoside requirements].

A report is given on a patient with ischaemic heart disease, whose recompensation in tachyarrhythmia absoluta was for some times possible only by means of unusually high doses of digitoxin (fully effective dose to 5.72 mg, maintenance dose to 0.4 mg). The patient survived a severe decompensation with pulmonary oedema, which appeared under "normal" applications of glycosides, 2 1/2 years under this therapy. Thus it must again be referred to an individual glycoside treatment.

Aged↗
PubMed1999

Adrenergic influence of uterine muscle contractions stimulated by a glycoside from the root of Dalbergia saxatilis.

The mechanism of uterine muscle contraction stimulated by a triterpenoid glycoside (dalsaxin) isolated from the root of D. saxatilis was investigated by in vitro methods in the rat. Dalsaxin caused a dose-related increase in uterine muscle contraction. The contraction was single and transient and was abolished by moderate doses of isoprenaline (1.80 nmol-0.40 mumol) and salbutamol (0.13-25 mumol). Adrenaline (9.10 nmol) also caused a reversible decrease (92.6%; P < 0.01) in myometrial contraction stimulated by this glycoside (0.24 mg/ml). Uterine muscle responses to dalsaxin (0.24 mg/ml) were enhanced by the beta-adrenergic receptor antagonist, propranolol, in a dose related manner. Atipamezole (1.50 ng/ml) but not prazosin (7.72 nmol-15.60 nmol) substantially reduced (80%; P < 0.01) myometrial contractions induced by this uterine spasmogen. The results suggest that dalsaxin enhances uterine muscle contraction by stimulating post junctional alpha 2-adrenergic receptors, presumably by inhibiting plasma membrane adenylate cyclase system and its associated increase in intracellular cAMP content.

Adrenergic alpha-Agonists↗
PubMed1975

Interrelation between glycosidic torsion, sugar pucker, and backbone conformation in 5'-beta-nucleotides. A 1H and 31P fast Fourier transform nuclear magnetic resonance investigation of the conformation of 8-aza-5'-beta-adenosine monophosphate and 8-aza-5'-beta-guanosine monophosphate.

Hydrogen-1 and phosphorus-31 nuclear magnetic resonance spectra of 5'-AMP, 5'-GMP, 8-aza-5'-GMP, adenosine, 8-aza-adenosine, and guanosine were obtained at biological pH values at a concentration sufficiently low to obtain information regarding their intramolecular solution conformation. The spectra were analyzed by computer simulation. It is shown that all of the above nucleosides and nucleotides have a flexible molecular framework in aqueous solution, 5'-AMP and 5'-GMP showing preference for anti(2-E in equilibrium 3-E)gg-g'g' conformations and the 8-aza analogs showing preference for (syn in equilibrium anti)-(2E in equilibrium 3-E) - g/t-g'g' conformations. In addition, aza substitution causes increase in 3-E sugar populations and in the populations of g'/t' conformers. It is argued that in the 8-aza analogs repulsive electrostatic interactions would prevail between --N (see article) at the 8 position and the negatively charged phosphate group, if the molecule existed in the anti-gg orientation. Such electrostatic repulsions can be relieved by rotating the C(4')--C(5') bond from gg to g/t orientations as well as by torsional variation about the glycosidic linkage from anti to syn conformation. Rotation from anti to syn orientation, for steric and electrostatic reasons, necessitates a simultaneous rotation about the C(4')--C(5') bond from gg to g/t conformation. The observation that the 8-aza substitution in 5'-beta-purine nucleotides cause a depopulation of gg and anti conformers with corresponding increase in the population of g/t and syn orientation seems to support the above thesis. The finding that rotational variation about a bond such as C(4')--C(5') is accompanied by torsional variation about C(5')--O(5') and the glycosidic bonds, as well as changes in the endocyclic torsion angles of the ribose moiety, gives important insight into the engineering of nucleic acid components: even though they in general prefer certain conformations, there is enough flexibility present in their molecular framework, that the entire system can undergo conformational adjustment in response to a perturbation. A conformational basis for the antileukemic effects of 8-aza purines is proposed.

Adenosine↗
PubMed2000

Fast repairing of oxidized OH radical adducts of dAMP and dGMP by phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl.

AIM: To investigate the antioxidative activity of the constituents of the roots of Scrophularia ningpoensis (Chinese name: Xuanshen). METHODS: The main compounds from the roots of Scrophularia ningpoensis were isolated and identified by chromatography and FABMS, NMR etc. Using the techniques of pulse radiolysis, the electron transfers from iridoid glycosides (IG) or phenylpropanoid glycosides (PG) to oxidized OH radical adducts of 2'-deoxyadenosine-5'-monophosphate acid (dAMP) or 2'-deoxyguanosine-5'-monophosphate acid (dGMP) were observed. RESULTS: Two IG: harpagoside and harpagide, two PG: angoroside C and acteoside were obtained as the main hydrophilic constituents of the plant. At 0.1 mmol/L concentration, angoroside C and acteoside were able to repair the oxidized OH adducts dAMP and dGMP significantly. However, harpagoside and harpagide had no such effect. The electron transfer rate constants of angoroside C with dAMP and dGMP were 4.2 x 10(8) and 10.3 x 10(8) L.mol-1.s-1; the electron transfer rate constants of acteoside with dAMP and dGMP were 5.3 x 10(8) and 20.2 x 10(8) L.mol-1.s-1. CONCLUSION: PG from Scrophularia ningpoensis have a potent antioxidative activity for reducing of the oxidized OH adducts of dAMP and dGMP.

Antioxidants↗
PubMed2003

Determination of the cardiac glycosides digoxin and digitoxin by liquid chromatography combined with isotope-dilution mass spectrometry (LC-IDMS)--a candidate reference measurement procedure.

This article describes a method of high analytical sensitivity, reproducibility and trueness for the determination of digoxin and digitoxin in serum or plasma at therapeutic levels using a combination of high-pressure liquid chromatography (HPLC), isotope-dilution mass spectrometry (IDMS) and caesium-adduct formation. A method for threefold deuterium substitution in the glycosides was developed, which could be performed within 24 hours without distillation giving yields > 98% of the theoretical value. Extraction from a serum or plasma matrix was performed using a liquid-phase extraction with ammonium acetate buffer/tertiary butylmethyl ether/ethyl acetate at pH 9.5. The HPLC-separation used a 10 x 2 mm LiChrospher RP-18 5 microm guard column in combination with a 125 x 2 mm main column of the same material and a gradient containing methanol, caesium ions and formic acid. Quantification of digoxin and digitoxin was made with IDMS using deuterated internal standards and the system run in single ion monitoring (SIM) mode. The methods had a lower limit of determination of 0.25 microg/l for digoxin and digitoxin, a trueness between 97.5 and 104% for digoxin and between 98 and 101% for digitoxin, respectively and had a coefficient of variation of less than 3% in the therapeutic range for both glycosides. Maximally 1 ml serum or plasma was needed for the procedure. The method is used to set target values for materials used in external quality assessment surveys (EQAS) run by INSTAND as part of a national EQAS-programme.)

Calibration↗
PubMed1976

Cardiac glycosides: relationship among active 86Rb uptake, (Na+,K+)-ATPase activity, and inotropy in guinea pig heart.

Relationships among positive inotropic responses, (Na+,K+)-ATPase inhibition, and sodium pump activities were studied using paced Langendorff preparations of guinea pig heart. (Na+,K+)-ATPase activity was estimated from the initial velocity of [3H] ouabain binding in ventricular homogenates, and sodium pump activity from ouabain-sensitive 86Rb uptake of ventricular slices. These parameters were measured in control, or in ouabain-or digitoxin-treated hearts either at the time of inotropic response or during the course of drug washout and compared with inotropy in the same heart. Perfusion of ouabain or digitoxin caused an increase in contractile force and a decrease in the initial velocity of ATP-dependent [3H] ouabain binding. The levels of [3H] ouabain binding in homogenates observed after a long incubation period were not different in ouabain-perfused and control homogenates, indicating that the nonlabeled ouabain bound to (Na+,K+)-ATPase during Langendorff perfusion was exchangeable with [3H] ouabain. Perfusion of drug-free solution after a 20-min perfusion of the isolated heart with either ouabain or digitoxin resulted in a loss of inotropic response and a recovery of the inhibition of the initial velocity of ATP-dependent [3H] ouabain binding. Inotropic responses to digitoxin during perfusion and subsequent loss during washout were accompanied by a reduction and subsequent recovery of ouabain-sensitive 86Rb uptake. Thus, it would appear that with cardiac glycosides, a relationship exists among cardiac contractile force, the inhibition of cardiac (Na+,K+)-ATPase, and the inhibition of the sodium pump activity. The inhibition of (Na+,K+)-ATPase and sodium pump because of cardiac glycoside perfusion of the isolated beating heart was reversible.

Adenosine Triphosphatases↗
PubMed2004

Induction of apoptosis by maackiain and trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) in human promyelotic leukemia HL-60 cells.

We have investigated the effects of maackiain and trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) on DNA of human promyelotic HL-60 leukemia cells. It was found that extent of induction of apoptosis by maackiain was larger than that by trifolirhizin in human leukemia HL-60 cells. Morphological changes showing apoptotic bodies were observed in the HL-60 cells treated with maackiain and trifolirhizin. The fragmentations of DNA by maackiain and trifolirhizin to oligonucleosomal-sized fragments that is a characteristic of apoptosis was observed to be concentration- and time-dependent in the HL-60 cells. The data of the present study show that the suppressions by maackiain and trifolrhizin of growth of the HL-60 cells result from the induction of apoptosis by these compounds, and that the extent of growth suppression and induction of apoptosis by maackiain was greater than that by the glycoside (trifolirhizin).

Antineoplastic Agents, Phytogenic↗
PubMed2004

[Phenylethanoid glycosides from root of Picrorhiza scrophulariiflora].

OBJECTIVE: To study the phenylethanoid glycosides from root of Picrorhiza scrophulariiflora. METHOD: Column chromatographic techniques were used for isolation and purification of chemical constituents of the plant and the structures were identified by spectroscopic analysis. RESULT: Six phenylethanoid glycosides were isolated and elucidated as: 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside (1), 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-beta-D-glucopyranosyl (1-->3) beta-D-glucopyranoside (2), scroside B (3), hemiphroside A (4), plantainoside D (5) and scroside A (6), respectively. CONCLUSION: Compounds 1, 2, 4 and 5 were isolated from this plant for the first time and compound 2 was firstly obtained from natural source.

Disaccharides↗
PubMed2005

Urinary pharmacokinetics of cyanidin glycosides in healthy young men following consumption of elderberry juice.

We investigated the urinary pharmacokinetics of monomeric anthocyanins in seven healthy volunteers. The volunteers were administered a single oral dose of 3.57 g total anthocyanins contained in 150 ml of a concentrated elderberry juice under fasting conditions. Within 24 h the urinary excretion of unchanged cyanidin-3,5-diglucoside (cyanidin-3-sambubioside-5-glucoside and cyanidin-3,5-diglucoside were calculated as cyanidin-3,5-diglucoside equivalents), cyanidin-3-glucoside, cyanidin-3-sambubioside and total anthocyanins (i.e., the sum of all quantifiable anthocyanidin glycosides) was 0.16, 0.06, 0.05 and 0.06% of the administered doses, respectively. Maximum excretion rates were determined within 1.0 h after intake. The estimates (arithmetic mean +/- SD) of t1/2 were 1.25 +/- 0.25, 1.53 +/- 0.36, 1.38 +/- 0.20 and 1.35 +/- 0.18 h for cyanidin-3,5-diglucoside, cyanidin-3-glucoside, cyanidin-3-sambubioside and total anthocyanins, respectively. The urinary excretion of intact anthocyanins was fast and the decline of excretion rates appeared to be monophasic, suggesting a one-compartment pharmacokinetic model. The low urinary excretion of dietary anthocyanidin glycosides with values below 1% indicates that a large proportion of these plant pigments consumed are metabolized before entry into the circulation.

Adult↗
PubMedDate not supplied

Digitalis glycosides accentuate the depressant effect of anoxia and reoxygenation on the cardiac myocyte: antagonism by amiloride.

The purpose of this study was to determine whether digitalis glycosides alter the effect of anoxia and reoxygenation on the cardiac myocytes and whether it could be modified by inhibition with amiloride. Cardiac myocytes aggregates were prepared from ventricles of 7 day old chick embryos and were maintained in culture. They were exposed to a 2 hr anoxia period followed by reoxygenation. Anoxia produced a significant reduction in contractile frequency. Ouabain, at low doses (10(-7) M and 10(-8) M), produced little effect in the absence of anoxia but produced a marked and significant (p less than 0.05) reduction in contractile frequency in the presence of anoxia. Myocytes exposed to anoxia stopped beating only in the presence of 10(-7) M and 10(-6) M ouabain and the time to cessation of spontaneous contraction was dependent on ouabain dose. Amiloride (10(-7) M or 10(-6) M) significantly (p less than 0.05) reduced but did not completely prevent the effect of ouabain. During reoxygenation, beating rate returned to base line in control cells and those exposed to ouabain (10(-8) M and 10(-7) M) but ouabain slowed the rate of recovery. This slowing of recovery, produced by ouabain, was prevented by amiloride. These findings indicate the potentially deleterious effects of digitalis glycosides in myocardial anoxia and reoxygenation and the ability of amiloride to oppose these adverse effects.

Amiloride↗
PubMed1989

[Individual glycoside therapy using serum concentration determination in heart insufficiency of horses].

23 horses and one donkey with congestive heart failure are treated with a standardized methyldigoxin dose (0.0032 mg/kg of body weight). The therapy is controlled by the serum concentration of the cardiac glycoside. 4 horses have a higher and 13 horses a lower serum concentration as necessary for therapeutic approach. The influence of additional diseases and medications is demonstrated. Finally a rule for the evaluation of the individual therapeutic glycoside-dose is given.

Animals↗
PubMed1985

Electron microscopic autoradiographic study of heart muscle calcium in experimental cardiac glycoside poisoning.

The role of calcium was investigated in myocardial cell necrosis induced by cardiac glycoside. Experimental poisoning caused an increase of Ca45. Excessive intracellular calcium uptake must be the determining factor in the aetiology of myocardial cell damage. The possible involvement of calcium increase in the genesis of cardiac glycoside induced myocardial cell necrosis is discussed.

Adenosine Triphosphatases↗
PubMed1985

Control of phenotypic expression of cultured B16 melanoma cells by plant glycosides.

The effects of two plant glycosides, ginsenosides Rh1 and Rh2, on the growth and differentiation of mouse melanoma (B16) cells in culture were studied. These plant glycosides have a dammarane skeleton resembling a steroid skeleton as an aglycone. Ginsenoside Rh2 inhibits the growth of B16 melanoma cells, causes morphological alterations, and stimulates melanogenesis at high cellular density. When ginsenoside Rh2 was removed after 2 or 6 days of treatment, the growth rate recovered slightly but not completely, during the period of observation (4 days after removal). On the other hand, ginsenoside Rh1 does not inhibit the growth of melanoma cells even at concentrations over 100 microM but stimulates the expression of the melanotic phenotype. Ginsenosides Rh1 and Rh2, possessing a glucose molecule at C-6 and C-3, respectively, have very similar chemical structures, but their effects on B16 melanoma cells differ remarkably. While it appears that the degree of differentiation is inversely related to cell growth, the present observations suggest that the differentiation and growth capacity of this B16 melanoma subline are independent phenotypic expressions.

Animals↗
PubMed1977

[Influence of high intravenous doses of D-penicillamine on toxic actions of cardiac glycosides in the guinea pig. Short communication (author's transl)].

Intravenous infusions of arrhythmogenic and lethal doses of ouabain and digoxin in anesthetized guinea pigs were not influenced by pretreatment with 1 g/kg D-penicillamine. The respective doses of proscillaridin and digitoxin, however, were significantly decreased by D-penicillamine. As could be demonstrated with proscillaridin this effect of D-penicillamine was dose-dependent between 0.25 and 1.0 g/kg. Obviously the strong plasma-protein binding of D-penicillamine leads to a displacement from binding sites of such cardiac glycosides which are also strongly bound to plasma proteins and thus reduces toxic doses of cardiac glycosides. Because of the extremely different doses of D-penicillamine in the animal experiments compared to those used therapeutically in man the present findings are irrelevant for clinical practice.

Animals↗
PubMed1984

Biological activity of glycosides of vitamin D3 and 1 alpha-hydroxyvitamin D3.

For the first time, the biological activity of the newly synthesized glycosides of vitamin D3 and of 1 alpha(OH)D3 has been studied in rats, chickens, and Japanese quails. Glucosidation did not reduce the activity of vitamin D3. In chickens, vitamin D3 glucoside has an activity of 90% to 95% as compared to the aglycon. In rats vitamin D3 glucoside is equally active when given by intravenous or oral route. Glycosides of 1 alpha (OH)D3, however, show a lower activity in rats, chickens, and quails. 1 alpha (OH)D3 glucoside has about 10% activity of the free 1 alpha (OH)D3, while 1 alpha (OH)D3 cellobioside is without any activity in chickens. 1 alpha (OH)D3 glucoside might be of interest, due to its broader therapeutical dosage range.

Administration, Oral↗
PubMed1984

[Report of experiences in the treatment of 16 cases of severe glycoside poisoning with digitalis antibody fragments (Fab)].

To date, 16 patients with severe glycoside poisoning have been treated with Fab as part of the clinical trial for efficacy and tolerance. The ages of the patients ranged from 4 to 77 years. In 13 cases, the substance was taken with suicidal intent. The following were considered to be indications for the use of Fab: the appearance of life-threatening arrhythmias as high-grade atrioventricular conduction disorders, multifocal ectopic beats, ventricular tachycardia, and relapsing ventricular fibrillation in 5 cases. Serum digoxin concentrations were between 3.8 and 78 ng/ml before the start of treatment. The amount of Fab administered was 240-800 mg, in the majority of cases 480 mg. Regression of the arrhythmias was seen in all patients during or shortly after the Fab infusion. There was a rapid fall in the free digoxin in the serum to levels that were no longer measurable and a marked rise in bound digoxin with a simultaneous intensive excretion of bound digoxin in the urine. Fab therapy is considered to be a major advance in the treatment of severe, previously fatal, glycoside poisoning. No notable side effects were observed, nor were there any allergic reactions to foreign protein.

Acetyldigoxins↗