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 469 records · Page 26Linked to original sources
PubMed2002

Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance).

Glycosidically bound compounds were isolated from the methanol extract of fresh rhizomes of smaller galanga (Alpinia officinarum Hance). Nine glycosides (1-9) were finally obtained by reversed-phase HPLC and their structures were elucidated by MS and NMR analyses. They were the three known glycosides, (1R,3S,4S)-trans-3-hydroxy-1,8-cineole beta-D-glucopyranoside (1), benzyl beta-D-glucopyranoside (3), and 1-O-beta-D-glucopyranosyl-4-allylbenzene (chavicol beta-D-glucopyranoside, 4); and the six novel glycosides, 3-methyl-but-2-en-1-yl beta-D-glucopyranoside (2), 1-hydroxy-2-O-beta-D-glucopyranosyl-4-allylbenzene (5), 1-O-beta-D-glucopyranosyl-2-hydroxy-4-allylbenzene (demethyleugenol beta-D-glucopyranoside, 6), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-2-hydroxy-4-allylbenzene (demethyleugenol beta-rutinoside, 7), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-4-allylbenzene (chavicol beta-rutinoside, 8), and 1,2-di-O-beta-D-glucopyranosyl-4-allylbenzene (9). Compounds 2-9 were detected for the first time as constituents of galanga rhizomes.

Carbohydrate Conformation↗
PubMed2003

Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits.

There is a growing interest in producing food plants with increased amounts of flavonoids because of their potential health benefits. Tomatoes contain small amounts of flavonoids, most of which are located in the peel of the fruit. It has been shown that flavonoid accumulation in tomato flesh, and hence an overall increase in flavonoid levels in tomato fruit, can be achieved by means of simultaneous overexpression of the maize transcription factors LC and C1. Fruit from progeny of two modified lines (2027 and 2059) was selected for a detailed analysis and individual identification of flavonoids, at different stages of maturity. Nine major flavonoids were detected in the flesh of transgenic ripe tomatoes. LC/NMR, LC/MS, and LC/MS/MS enabled us to identify these as kaempferol-3,7-di-O-glucoside (1), kaempferol-3-O-rutinoside-7-O-glucoside (2), two dihydrokaempferol-O-hexosides (3 and 4), rutin (5), kaempferol-3-O-rutinoside (6), kaempferol-3-O-glucoside (7), naringenin-7-O-glucoside (8) and naringenin chalcone (9), which were quantified by HPLC/DAD. All but 5, 6, and 9 were detected in tomato for the first time. The total flavonoid glycoside content of ripe transgenic tomatoes of line 2059 was about 10-fold higher than that of the controls, and kaempferol glycosides accounted for 60% of this. Kaempferol glycosides comprised around 5% of the flavonoid glycoside content of ripe control tomatoes (the rest was rutin and naringenin chalcone). The rutin concentration in both transgenic and control fruits was similar.

Chromatography, High Pressure Liquid↗
PubMed2006

The flavonoid glycosides and procyanidin composition of Deglet Noor dates (Phoenix dactylifera).

The fruits of the date palm (Phoenix dactylifera) are consumed throughout the world and are an important part of the diet in the Middle East. Dates at the rutab and tamar maturity and ripening stages contain a wide array of phenolic antioxidants, but little is known about the composition of phenolic compounds in dates at the khalal stage of ripening. In the current study, the flavonoid glycoside and procyanidin compositions of dates of the cultivar Deglet Noor harvested at the khalal stage of maturity were characterized using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI/MS/MS). Procyanidin oligomers through decamers were identified in extracts of these dates. Higher molecular weight polymers, undecamers through heptadecamers, were also apparent from mass spectra. Thirteen flavonoid glycosides of luteolin, quercetin, and apigenin, 19 when considering isomeric forms, were also identified. Mass spectra indicate that both methylated and sulfated forms of luteolin and quercetin are present as mono-, di-, and triglycosylated conjugates whereas apigenin is present as only the diglycoside. LC-ESI/MS/MS spectra indicate that quercetin and luteolin formed primarily O-glycosidic linkages whereas apigenin is present as the C-glycoside.

Arecaceae↗
PubMed2006

Nondestructive determination of lignans and lignan glycosides in sesame seeds by near infrared reflectance spectroscopy.

Sesame (Sesamum indicum L.) contains abundant lignans including lipid-soluble lignans (sesamin and sesamolin) and water-soluble lignan glycosides (sesaminol triglucoside and sesaminol diglucoside) related to antioxidative activity. In this study, near infrared reflectance spectroscopy (NIRS) was used to develop a rapid and nondestructive method for the determination of lignan contents on intact sesame seeds. Ninety-three intact seeds were scanned in the reflectance mode of a scanning monochromator. This scanning procedure did not require the pulverization of samples, allowing each analysis to be completed within minutes. Reference values for lignan contents were obtained by high-performance liquid chromatography analysis. Calibration equations for lignans (sesamin and sesamolin) and lignan glycosides (sesaminol triglucoside and sesaminol diglucoside) contents were developed using modified partial least squares regression with internal cross-validation (n = 63). The equations obtained had low standard errors of cross-validation and moderate R2 (coefficient of determination in calibration). The prediction of an external validation set (n = 30) showed significant correlation between reference values and NIRS predicted values based on the SEP (standard error of prediction), bias, and r2 (coefficient of determination in prediction). The models developed in this study had relatively higher values (more than 2.0) of SD/SEP(C) for all lignans and lignan glycosides except for sesaminol diglucoside, which had a minor amount, indicating good correlation between the reference and the NIRS estimate. The results showed that NIRS, a nondestructive screening method, could be used to rapidly determine lignan and lignan glycoside contents in the breeding programs for high quality sesame.

Calibration↗
PubMed1977

Synthesis of episilon-rhodomycinone glycosides.

Twenty-six episilon-rhodomycinone glycosides have been synthesized. These include the episilon-rhodomycinone glycosides of 2-deoxy-L-fucose, 2-deoxy-L-rhamnose, and 2-deoxy-D-ribose as well as their 2-hydroxyl derivatives. NMR spectroscopy showed that all the glycosides prepared had the saccharide residues linked to position 10 of episilon-rhodomycinone and helped establish the anomeric purity and configuration of several glycosides. Preliminary screening results show that 2-deoxy-di-O-acetyl-D-ribopyranosyl-episilon-rhodomycinone has an activity T/C of 125 on P388 tumors.

Animals↗
PubMed1985

Conformational factors in cardiac glycoside activity.

Gomphoside, a 5 alpha-H cardiac glycoside isolated from Asclepias fructicosa, has an unique double glycosidic linkage to the aglycon through oxygen atoms at 2 alpha and 3 beta of the steroid. The 3'-axial hydroxyl of its conformationally rigid sugar residue appears to be the functional group responsible for its potent inotropic activity. With use of gomphoside as the model compound, the conformation of the flexible glycosidic linkage of the 5 beta-H cardenolides, digitoxigenin alpha-L-rhamnoside and digitoxigenin beta-D-digitoxoside, and the 5 alpha-H cardenolides, uzarigenin alpha-L-rhamnoside and uzarigenin beta-D-6-deoxyalloside, were investigated with the aid of computer graphics and conformational potential energy calculations. The relative inotropic potencies of these cardenolides can be accounted for by considering their active binding conformations with their potential energy distributions. The conformational distribution of the glycosidic moiety was postulated to be the major determinant of the biological activity of these cardenolides.

Animals↗
PubMed2002

Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis.

Two new sulfated triterpene glycosides, hemoiedemosides A (1) and B (2), have been isolated from the Patagonian sea cucumber Hemoiedema spectabilis. Their structures have been established by a combination of spectroscopic analysis (NMR and FABMS) and chemical transformations. Both glycosides present the same aglycon and differ in the degree of sulfation of the tetrasaccharide chain. Hemoiedemoside B (2) is a new example of a small number of trisulfated triterpene glycosides from sea cucumbers belonging to the family Cucumariidae. Glycosides 1 and 2 exhibit considerable antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum, while the semisynthetic desulfated derivative 1a is less active.

Animals↗
PubMedDate not supplied

Plant metabolites. Structure and in vitro antiviral activity of quinovic acid glycosides from Uncaria tomentosa and Guettarda platypoda.

A reinvestigation of the bark of Uncaria tomentosa afforded, in addition to the major quinovic acid glycosides 1-3, three further glycosides 4-6. The structures were elucidated by spectral and chemical studies. Furthermore, a series of antiviral tests were performed on all these glycosides and on the related glycosides 7-9, previously isolated from Guettarda platypoda.

Antiviral Agents↗
PubMed1993

Starfish saponins, part 49. New cytotoxic steroidal glycosides from the starfish Fromia monilis.

Nine new cytotoxic steroidal glycosides 1-9 have been isolated from the starfish Fromia monilis collected off New Caledonia. Structures of these compounds, which include four mono-(1-4), two di-(5,6), and three glycosides (7-9), were elucidated through spectral interpretation. Monilosides G [7], H [8], and I [9] are the first tri-glycosides to be found among the group of glycosides of polyhydroxilated steroids from starfishes.

Animals↗
PubMed1996

Isolation of 20 glycosides from the starfish Henricia downeyae, collected in the Gulf of Mexico.

Thirteen new (1-13) and seven known (14-20) steroid glycosides were isolated from Henricia downeyae, collected from the offshore waters of the northern Gulf of Mexico. Ethanolic extracts of these starfish caused growth inhibition in bacteria and fungi, potent antifouling activity against barnacle and bryozoan larvae, and feeding deterrent activity against a marine fish. The known compounds are typical glycosides found in several species of the family Echinasteridae, i.e., Echinaster sp. and Henricia laeviuscola. One of the new compounds belongs to this group, whereas the remaining 12 new compounds represent a novel series of steroid glycosides which have aglycons with structural similarities to the "asterosaponins". They possess a delta 9(11) 3 beta, 6 alpha-dihydroxysteroidal aglycon with 23-oxo or 22,23-epoxy functionalities and often a 20-hydroxyl group in the side chain. The sulfate is located at C-6 and the saccharide moiety at C-3, in contrast with the asterosaponins which have the sulfate at C-3 and the oligosaccaride moiety at C-6. All the new compounds contain a glucuronic acid unit, which is uncommon among steroid glycosides from echinoderms. The structures of the new compounds, isolated in amounts ranging from 3.4 to 0.9 mg, were determined by interpretation of their spectral data and by comparison with spectral data of known compounds.

Animals↗
PubMed1999

Components of the ether-insoluble resin glycoside fraction from the seed of Cuscuta australis.

An ether-insoluble resin glycoside fraction was obtained from the seeds of Cuscuta australis. Identification and characterization of alkaline hydrolysis products by means of GC, FABMS, and 1H, 13C, and 2D NMR revealed the material to be composed of three new glycosidic acids, cuscutic acids A1-A3 (1-3); triglycosides with (11S)-jalapinolic or (11S)-convolvulinolic acid as the aglycon; and acetic, isobutyric, (2S)-2-methylbutyric, tiglic, and (2R,3R)-nilic acids. The resin glycoside is considered to be a complex mixture of glycosidic ester-type oligomers (up to heptamers) with a core consisting of a number of the above cuscutic acids each acylated with one or two carboxylic acid moieties.

Carbohydrate Sequence↗
PubMed1999

Sucrose esters and xanthone C-glycosides from the roots of Polygala sibirica.

Six new sucrose esters, sibiricoses A(1)-A(6) (1-6), two new xanthone C-glycosides, sibiricaxanthones A (7) and B (8), and a new acetophenone glycoside, sibiricaphenone (9), were isolated from the roots of Polygala sibirica together with six known glycosides. The structures of new compounds were elucidated on the basis of chemical and spectroscopic evidence. The structure of the known xanthone glycoside, polygalaxanthone III (10), was revised.

Carbohydrate Sequence↗
PubMed2002

Constraints on effectiveness of cyanogenic glycosides in herbivore defense.

Cyanogenesis is the process by which hydrogen cyanide is released from endogenous cyanide containing compounds. Many cyanogenic plants release HCN in sufficient quantities to be toxic and, as a result, tend to be avoided by herbivores. However, there are many exceptions with some herbivores either immune to the cyanogenic status of the plant, or in some cases attracted to cyanogenic plants. This has led to a certain degree of scepticism regarding the role of cyanogenic glycosides as defense compounds. In this review, we examine evidence showing that differences in the effectiveness of cyanogenic glycosides in deterring herbivory can usually be reconciled when the morphology, physiology, and behavior of the animals, together with the concentration of cyanogenic glycosides in the host plant, are taken into account. Cyanogenic glycosides are not effective against all herbivores, and not all cyanogenic plants release enough cyanide to be considered toxic. Nevertheless, they do form part of the broad spectrum of toxic and distasteful compounds that herbivores must accommodate if they are to feed on cyanogenic plants.

Adaptation, Physiological↗
PubMed2004

Microarray analysis of gene expression on herbal glycoside recipes improving deficient ability of spatial learning memory in ischemic mice.

In order to reveal the mechanism of herbal glycoside recipes retrieving deficient ability of spatial learning memory in mice suffering from cerebral ischemia/reperfusion, a microarray system was used to analyze gene expression in those groups with increasing ability of spatial learning memory who were different from ischemic mice. In this work, we reported a comprehensive characterization of gene expression profiles of mouse hippocampus by the use of cDNA microarray system containing 1176 known genes in middle cerebral artery occlusion (MCAO) ischemic mice after treating with different dosage recipes of glycoside herbs (30, 90, and 270 mg/kg). The ability of spatial learning memory in ischemic mice was found to be decreased. The pathological process in ischemic mouse brain showed that a complex related to 100 genes' expression yielded 1.8-fold. Dose-dependent effects showed an improvement in the deficient ability and reduction in infarct volume when treated with glycoside recipes. Many genes (38-46) in expression were found greater than 1.8-fold in those effective recipes groups, including genes in cell cycle regulation, signal transduction, nerve system transcription factors, DNA binding protein, etc. Nine genes related to retrieving deficient ability of spatial learning memory treated with glycoside recipes were also found in this study. These results suggest that microarray analysis of gene expression might be useful for elucidating the mechanisms of pharmacological function of recipes.

14-3-3 Proteins↗
PubMed2000

A new acylated flavonol glycoside and antioxidant effects of Hedyotis diffusa.

A study on the bioactive principles of Hedyotis diffusa Willd., led to the isolation of a new acyl flavonol di-glycoside which was characterized as kaempferol 3-O[2"-O-(E-6'"-O-feruloyl)-beta-D-glucopyranosyl]-beta-D-galactop yranoside by spectral and chemical methods from the methanolic extract. In addition, three known flavonol glycosides and six known iridoid glycosides were also obtained. The above-mentioned glycosides were tested for antioxidant effects on xanthine oxidase inhibition, xanthine-xanthine oxidase cytochrome c and TBA-MDA systems.

Acylation↗
PubMed2003

Anticomplement and antioxidant activities of new acetylated flavonoid glycosides from Centaurium spicatum.

In addition to the three acetylated flavonol glycosides, quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-beta-galactopyranoside, quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-3-acetyl-beta-galactopyranoside, and quercetin 3- O-[(2,3,4- triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-4-acetyl-beta-galactopyranoside, which have recently been isolated from Centaurium spicatum (L.) Fritsch (Gentianaceae), a new pentaacetylated flavonoid glycoside was isolated from the same plant. Structure elucidation, especially the localization of the acetyl groups, and complete (1)H- and (13)C-NMR assignments, was carried out using one- and two-dimensional NMR methods, including (1)H- and (13)C-NMR, DEPT-135 and DEPT-90, and gradient-assisted experiments such as DQF-COSY, TOCSY, HSQC and HMBC. The structure of the new flavonoid glycoside was established as quercetin 3- O-[(2,3,4-triacetyl-alpha-rhamnopyranosyl)-(1-->6)]-3,4-diacetyl-beta-galactopyranoside. The anticomplement and antioxidant activities of these compounds were evaluated. The triacetylated flavonoid glycoside showed the highest activity in the two assays.

Antioxidants↗
PubMed2006

Cardiac glycosides provide neuroprotection against ischemic stroke: discovery by a brain slice-based compound screening platform.

We report here the results of a chemical genetic screen using small molecules with known pharmacologies coupled with a cortical brain slice-based model for ischemic stroke. We identified a small-molecule compound not previously appreciated to have neuroprotective action in ischemic stroke, the cardiac glycoside neriifolin, and demonstrated that its properties in the brain slice assay included delayed therapeutic potential exceeding 6 h. Neriifolin is structurally related to the digitalis class of cardiac glycosides, and its putative target is the Na(+)/K(+)-ATPase. Other cardiac glycoside compounds tested also showed neuroprotective activity, although with lower apparent potencies. In subsequent whole-animal studies, we found that neriifolin provided significant neuroprotection in a neonatal model of hypoxia/ischemia and in a middle cerebral artery occlusion model of transient focal ischemia. The neuroprotective potential of Na(+)/K(+)-ATPase is of particular interest because of its known "druggability"; indeed, Food and Drug Administration-approved, small-molecule compounds such as digitoxin and digoxin have been in clinical usage for congestive heart failure and arrhythmias for several decades. Thus, an existing cardiac glycoside or closely related compound could provide an accelerated path toward clinical trial testing for ischemic stroke. Our findings underscore the important role that hypothesis-neutral, high-content, tissue-based screens can play in the identification of new candidate drugs and drug targets for the treatment of diseases for which validated therapeutic pathways are not currently available.

Aging↗
PubMed2000

Substrate specificity in glycoside hydrolase family 10. Structural and kinetic analysis of the Streptomyces lividans xylanase 10A.

Endoxylanases are a group of enzymes that hydrolyze the beta-1, 4-linked xylose backbone of xylans. They are predominantly found in two discrete sequence families known as glycoside hydrolase families 10 and 11. The Streptomyces lividans xylanase Xyl10A is a family 10 enzyme, the native structure of which has previously been determined by x-ray crystallography at a 2.6 A resolution (Derewenda, U., Swenson, L., Green, R., Wei, Y., Morosoli, R., Shareck, F., Kluepfel, D., and Derewenda, Z. S. (1994) J. Biol. Chem. 269, 20811-20814). Here, we report the native structure of Xyl10A refined at a resolution of 1.2 A, which reveals many features such as the rare occurrence of a discretely disordered disulfide bond between residues Cys-168 and Cys-201. In order to investigate substrate binding and specificity in glycoside hydrolase family 10, the covalent xylobiosyl enzyme and the covalent cellobiosyl enzyme intermediates of Xyl10A were trapped through the use of appropriate 2-fluoroglycosides. The alpha-linked intermediate with the nucleophile, Glu-236, is in a (4)C(1) chair conformation as previously observed in the family 10 enzyme Cex from Cellulomonas fimi (Notenboom, V., Birsan, C., Warren, R. A. J., Withers, S. G., and Rose, D. R. (1998) Biochemistry 37, 4751-4758). The different interactions of Xyl10A with the xylobiosyl and cellobiosyl moieties, notably conformational changes in the -2 and -1 subsites, together with the observed kinetics on a range of aryl glycosides, shed new light on substrate specificity in glycoside hydrolase family 10.

Glycoside Hydrolases↗