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 1,333 records · Page 74Linked to original sources
PubMed1984

Effects of thyroid hormone on sodium pump sites, sodium content, and contractile responses to cardiac glycosides in cultured chick ventricular cells.

Sensitivity of cardiac muscle to digitalis glycosides depends on the thyroid state. The mechanism of this interaction was investigated at the cellular level using spontaneously beating monolayers of cultured chick embryo ventricular cells. Cells were grown for 48 h in serum-free medium containing concentrations of triiodothyronine (T3) from zero to 10(-7) M, and the total number of sodium pump sites, sodium content, and contractile amplitude in the presence and absence of various concentrations of ouabain were determined. T3 caused a concentration-dependent increase in the number of specific ouabain binding sites; the maximal increase to 160% of control was observed in response to 10(-8) M T3. T3 lowered steady-state cellular sodium content in a concentration-dependent manner, also. Ouabain (1 microM) exposure elevated cellular sodium content in all cells, but the increase was greatest in cells grown in T3-free medium and least in cells grown in 10(-8) M T3. The positive inotropic and toxic effects of ouabain in cells grown in 10(-8) M T3 were diminished at any given ouabain concentration, and thus, the dose-response curve was shifted to the right. These results indicate that T3 causes induction of additional sodium pump sites that are functional. The increased tolerance of hyperthyroid cells and reduced tolerance of hypothyroid cells to cardiac glycosides can be explained by these changes in the number of sodium pump sites and cellular sodium content, and consequently, calcium influx via sodium-calcium exchange.

Animals↗
PubMed2005

Pharmacokinetics of anthocyanidin-3-glycosides following consumption of Hibiscus sabdariffa L. extract.

Pharmacokinetic parameters of several dietary anthocyanins following consumption of Hibiscus sabdariffa L. extract were determined in 6 healthy volunteers. Subjects were given a single oral dose of 150 mL of Hibiscus sabdariffa L. extract yielding 62.6 mg of cyanidin-3-sambubioside, 81.6 mg of delphindin-3-sambubioside, and 147.4 mg of total anthocyanins (calculated as cyanidin equivalents). Within 7 hours, the urinary excretion of cyanidin-3-sambubioside, delphinidin-3-sambubioside, and total anthocyanins (ie, the sum of all quantifiable anthocyanidin glycosides) was 0.016%, 0.021%, and 0.018% of the administered doses, respectively. Maximum excretion rates were determined at 1.5 to 2.0 hours after intake. The dose-normalized plasma area under the curve estimates were 0.076, 0.032, and 0.050 ng x h/mL/mg for cyanidin-3-sambubioside, delphinidin-3-sambubioside, and total anthocyanins, respectively. The dose-normalized C(max) estimates were 0.036, 0.015, and 0.023 ng/mL/mg in the same sequence. They were reached each at 1.5 hours (median) after intake. The geometric means of t1/2 were 2.18, 3.34, and 2.63 hours for cyanidin-3-sambubioside, delphinidin-3-sambubioside, and total anthocyanins, respectively. The urinary excretion of intact anthocyanins was fast and appeared to be monoexponential. To evaluate the contribution of anthocyanins to the health-protecting effects of Hibiscus sabdariffa L. extract, it will be necessary to perform further studies on both the intact glycosides and their in vivo metabolites or conjugates in human plasma and urine.

Administration, Oral↗
PubMed1987

Cardiac glycoside toxicity resulting from cough linctus abuse.

Proprietry cough medicines are often abused by drug addicts as they are freely available and, in many instances, contain narcotic substances. A variety of other compounds are present in these products, including compounds structurally related to the commonly prescribed cardiac glycosides. We report a case in which severe cardiac glycoside toxicity resulted from the abuse of such a preparation.

Adult↗
PubMed1999

Antioxidant properties of flavonol glycosides from tea.

We have determined the antioxidant activity of the major flavonols found in tea: a monoglycoside, a diglycoside and two triglycosides of kaempferol and three monoglycosides, a diglycoside and two triglycosides of quercetin. The Trolox equivalent antioxidant capacity (TEAC) and inhibition of iron/ascorbate-induced lipid peroxidation of phosphatidyl choline vesicles were measured. In the aqueous phase TEAC assay, the quercetin monoglycosides and diglycoside were approximately half as effective as quercetin aglycone. The quercetin triglycosides were much less effective than the monoglycosides and the diglycoside. The kaempferol glycosides were 32-39% less effective in the aqueous phase antioxidant assay compared to the kaempferol aglycone. Quercetin monoglycosides and diglycoside were potent inhibitors of lipid peroxidation, in contrast to the triglycoside which was much less effective. All the kaempferol glycosides were significantly less potent inhibitors of lipid peroxidation compared to the kaempferol aglycone. The compounds described herein demonstrate the antioxidant activity of the major flavonols in tea and indicate the effect of substituting a range of sugar moieties in the phenolic C ring.

Antioxidants↗
PubMed1999

Antioxidant properties of flavonol glycosides from green beans.

We have examined the antioxidant activity of one class of polyphenolic compounds in green beans: two novel flavonol glycosides (quercetin 3-O-[xylosyl(1-->2)]-rhamnosyl (1-->6)-glucoside and the corresponding kaempferol analogue), quercetin 3-O-glucuronide, kaempferol 3-O-glucuronide, quercetin 3-O-rutinoside and kaempferol 3-O-rutinoside. The Trolox equivalent antioxidant capacity (TEAC) and inhibition of iron/ascorbate-induced lipid peroxidation of phosphatidyl choline vesicles were measured. In the aqueous phase TEAC assay, the glucuronide and rutinoside of quercetin were good antioxidants, but not as effective as the quercetin aglycone. TEAC values for the glucuronide and other glycosides of kaempferol were much lower than the corresponding quercetin species but similar to that of the kaempferol aglycone. Quercetin 3-O-glucuronide and quercetin 3-O-rutinoside were both potent inhibitors of lipid peroxidation, in contrast to the those of kaempferol. The compounds described herein demonstrate the antioxidant activity of the flavonols present in green beans and indicate the effect on antioxidant activity of sugar substitutions in the phenolic C ring.

Antioxidants↗
PubMed2000

Immunostimulatory effects of cycloartane-type triterpene glycosides from astragalus species.

In the course of our research on the oligoglycosidic constituents of Turkish Astragalus species, we have isolated a number of cycloartane-type triterpene glycosides. The current study examines the immunostimulatory effects of nineteen of these cycloartane-type compounds using a transcription-based bioassay for Nuclear Factor kappa B (NF-kappaB) activation in a human macrophage/monocyte cell line, THP-1. All compounds were inactive at 100 microg/ml except astragaloside I which increased NF-kappaB directed luciferase expression to levels about 65% as compared with maximal stimulation by E. coli lipopolysaccharide (LPS) at 10 microg/ml. None of the compounds were active at low dosage levels (0.1 microg/ml) in combination with 50 ng/ml LPS. Astragaloside I also increased mRNA expression of the inflammatory cytokines interleukin-1beta (IL-1beta) and tumor necrosis factor-alpha (TNF-alpha) as measured using reverse transcriptase-polymerase chain reaction (RT)-PCR. Based on these results it is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.

Adjuvants, Immunologic↗
PubMed2003

Scropolioside-D2 and harpagoside-B: two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity.

Five iridoid glycosides, including the two new compounds scropolioside-D(2) (1) and harpagoside-B (2), were isolated from the aerial parts of Scrophularia deserti DEL (Scrophulariaceae). Their structures were elucidated on the basis of spectral data to be 6-O-[2",4"-di-O-acetyl-3"-O-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]-8 alpha-hydroxymethyl-1 alpha,5 beta,6 alpha,7 alpha,9 beta-pentahydro-7(8)-epoxy-2-oxaind-3-ene-1-O-beta-D-glucopyranoside-6'-O-acetate (1) and 5-O-beta-hydroxy-8-O-beta-trans-cinnamoyl-8 alpha-methyl-1,6,7,9-tetrahydro-2-oxaind-3-ene-1-O-beta-D-glucopyranoside (2), respectively. In addition, three more iridoid glycosides, scropolioside-D (3), koelzioside (4), and 8-O-acetyl-harpagide (5), were also isolated and characterized from this source. The biological activity and the structure activity relationship of the compounds were also studied, and scropolioside-D (3) and harpagoside-B (2) were found to possess significant antidiabetic and antiinflammatory activity, respectively.

Animals↗
PubMed2005

Nardostachys chinensis glycoside induces characteristics of neuronal differentiation in rat pheochromocytoma PC12 cells.

Rat pheochromocytoma PC12 cells undergo neuronal differentiation in response to nerve growth factor. We show here that exposure of PC12 cells to Nardostachys chinensis glycoside induces the outgrowth of neurites, increases the activity of AChE, triggers cell cycle arrest in G1 and enhances the expression of growth associated protein 43 (GAP-43). Both the outgrowth of neurites and the increase in AChE activity are prevented partly by PD98059, a specific inhibitor of MEK1. These results suggest that N. chinensis glycoside induces the characteristics of neuronal differentiation in PC12 cells via the mitogen-activated protein kinase (MAPK)-related signal cascade.

Animals↗
PubMed1989

Ionophoretic activities of oligopeptide lactones and resin-glycosides in human erythrocytes.

Oligopeptide lactones (theonellapeptolides) isolated from the Okinawan marine sponge Theonella swinhoei and resin-glycosides (merremosides) from the tuber of an Indonesian medicinal plant Merremia mammosa were examined regarding their activities in transporting Na+, K+, and Ca++ ions into human erythrocytes. Each of these lactones, which had been shown, using a supported liquid membrane, to have an ionophoretic effect on the alkali metal ions, transported the ions to a different extent. The ion transporting activities of these compounds were completely lost when the macrocyclic lactone structures were cleaved by sodium methylate. Resin-glycosides with an additional branched glycosyl residue showed much greater ion transporting activities than those without it.

Erythrocytes↗
PubMed1992

Triterpene glycosides from the bark of Robinia pseudo-acacia L. I.

From the bark of Robinia pseudo-acacia L., five new triterpene glycosides, robiniosides A-D (3, 5-7) and compound III (4), were isolated and their structures were elucidated as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D- glucuronopyranosyl 3 beta,22 beta-dihydroxyolean-12-en-29-oic acid (3), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl(1-->2)-beta-D -glucuronopyranosyl 3 beta,22 beta,24-trihydroxyolean-12-en-29-oic acid (4), whose sapogenol was unambiguously characterized and designated as oxytrogenin, 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D glucuronopyranosyl oxytrogen (5), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl oxytrogenin 22-O-alpha-L-rhamnopyranoside (6), 3-O-alpha-L- rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D-glucuronop yranosyl oxytrogenin 22-O-alpha-L-rhamnopyranoside (7), respectively, together with two known triterpene glycosides, kaikasaponin III (1) and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-galactopyranosyl(1-->2)-beta-D - glucuronopyranosyl 3 beta,22 beta-dihydroxyolean-12-en-29-oic acid (2).

Carbohydrate Sequence↗
PubMed1994

Analysis of conjugated bile acids in human biological fluids. Synthesis of hyodeoxycholic acid 3- and 6-glycosides and related compounds.

The glucuronide, glucoside and N-acetylglucosaminide conjugates of hyodeoxycholic acid were synthesized. In addition, murideoxycholic acid 3-glycosides and some of their C-5 epimeric analogs were also prepared. The principal reactions used are 1) the Koenigs-Knorr condensation reaction of 3-oxo-6 alpha-hydroxy and 6-oxo-3 alpha-hydroxy esters with an appropriate alpha-acetohalosugar catalyzed by cadmium carbonate in benzene under reflux, 2) reduction of the resulting bile acid glycoside methyl ester-acetates with tert-butylamine-borane complex, and 3) subsequent hydrolysis with aqueous lithium hydroxide.

Bile Acids and Salts↗
PubMed1996

Indonesian medicinal plants. XV. Chemical structures of five new resin-glycosides, merremosides a, b, c, d, and e, from the tuber of Merremia mammosa (Convolvulaceae).

Five new resin-glycosides, named merremosides a (1), b (2), c (3), d (4), and e (5), were isolated from the tuber of Merremia mammosa (LOUR.) HALLIER f. (Convolvulaceae), an Indonesian medicinal plant. The structures of 1, 2, 3, 4, and 5 have been elucidated on the basis of chemical and physiochemical evidence, including syntheses of (11S)-(+)- and (11R)-(--)-jalapinolic acid (16b and 18b) and the glycosidic acid designated as merremoside i (6).

Carbohydrate Sequence↗
PubMed1997

Indonesian medicinal plants. XIX. 1) Chemical structures of four additional resin-glycosides, mammosides A, B, H1, and H2, from the tuber of Merremia mammosa (Convolvulaceae).

Four new resin-glycosides, named mammosides A (10), B (11), H1 (12), and H2 (13), were isolated from the tuber of Merremia mammosa (Convolvulaceae), a Jamu raw material. Their chemical structures have been elucidated on the bases of chemical and physicochemical evidence, including synthesis of a glycosidic acid designated as mammoside I.

Carbohydrate Sequence↗
PubMed1998

Pregnane glycosides, gymnepregosides A-F from the roots of Gymnema alternifolium.

The structural elucidation of six new related polyoxypregnane glycosides, gymnepregosides A (1), B (2), C (3), D (4), E (5) and F (6), together with two known compounds, from the roots of Gymnema alternifolium (Asclepiadaceae) was achieved through on a detailed study of 1H- and 13C-NMR spectral data and chemical means. The results obtained for new compounds, 1-6, show that they are (20S)-pregn-6-ene-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptaol or sarcostin 3-O-glycosides, and all the sugars at C-3 are beta(1-->4)-linked. Some of them possessed benzoyl, cinnamoyl and tigloyl residues as the ester linkages located at C-12 and/or C-20 of the aglycon.

Carbohydrate Sequence↗
PubMed1999

Pregnane glycosides, gymnepregosides G-Q from the roots of Gymnema alternifolium.

The structural elucidation of eleven new related polyoxypregnane glycosides, gymnepregosides G (1), H (2), I (3), J (4), K (5), L (6), M (7), N (8), O (9), P (10) and Q (11), from the roots of Gymnema alternifolium (Asclepiadaceae) was achieved by a detailed study of 1H- and 13C-NMR spectral data and chemical means. The results obtained for new compounds, 1-11, show that they are (20S)-pregn-6-ene-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptaol 3-O-glycosides, and all the sugars at C-3 are beta(i-->4)-linked. Some of them possess benzoyl, (E)- and (Z)-cin-namoyl, and tigloyl residues as the ester linkages located at C-12 and/or C-20 of the aglycone.

Carbohydrate Sequence↗
PubMed2000

Constituents of a fern, Diplazium subsinuatum. III. Four new hopane-triterpene lactone glycosides.

From a whole plant of a fern, Diplazium subsinuatum, three new hopane-triterpene lactone glycosides, diplaziosides V-VII (1-3), were isolated, together with a new monoacetyl derivative (4) of diplazioside VII (3). Compounds 1-3 were defined as the respective 3-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosides of 3beta,24-dihydroxyhopan-28,22-olide (1), of 3beta,17,24-trihydroxyhopan-28,22-olide (2), and of (22R)-3beta,24,30-trihydroxyhopan-28,22-olide (3), and 4 as the 6"-O-acetate of 3, respectively, on the basis of spectral evidence. 1-3 are new in their glycoside structures but also in their triterpene structures. Furthermore, in compounds 1-4, the coupling between the 24-hydroxy proton and one of the 24-methylene protons showed a very large J-value (11.4 Hz); based on this 1H-NMR evidence, etc., preferred conformations of the 24-hydroxymethylene groups in 1-4 are also inferred. In a similar manner, 1H-NMR coupling patterns of the 24-hydroxymethylene in the monoglucoside (2a) and aglycone (2b), derived from 2, are also reported and discussed here.

Glycosides↗
PubMed2000

New monoterpene glycoside esters and phenolic constituents of Paeoniae radix, and increase of water solubility of proanthocyanidins in the presence of paeoniflorin.

Seven new monoterpene glycoside esters related to paeoniflorin were isolated from Paeoniae Radix, together with polymeric proanthocyanidins, polygalloylglucoses and 48 known compounds (a benzoylsucrose, seven aromatic acids, adenosine, nine monoterpene glycosides, eight flavan-3-ols, a catechin dimer formed by oxidation, seven proanthocyanidins, three galloylsucroses, five galloylglucoses, and six ellagitannins). The structures of the new compounds were determined by spectral investigation including two-dimensional NMR techniques. In addition, increased water solubility of polymeric proanthocyanidin in the presence of paeoniflorin was examined by n-octanol-water partition and 1H-NMR spectral experiments.

Anthocyanins↗