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At least 1,279 records · Page 71Linked to original sources
PubMed2005

Xanthone glycosides from Swertia franchetiana.

A new xanthone glycoside (1) has been isolated from Swertia franchetiana together with five known xanthone glycosides. Their structures were elucidated as 7-O-[beta-D-xylopyranosyl-(1-->2)-beta-D-xylopyranosyl]-1,7,8-trihydroxy-3-methoxyxanthone (1), 7-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl]-1,7,8-trihydroxy-3-methoxyxanthone (2), 8-O-beta-D-glucopyranosyl-1,3,5,8-tetrahydroxyxanthone (3), 1-O-beta-D-glucopyranosyl-1-hydroxy-3,7,8-trimethoxyxanthone (4), 1-O-[beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-1-hydroxy-2,3,5-trimethoxyxanthone (5) and 1-O-[beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-1-hydroxy-3,5-dimethoxyxanthone (6) on the basis of spectroscopic evidence.

Chromatography, Gel↗
PubMed2005

Triterpenoid glycoside from Cimicifuga racemosa.

One new triterpene glycoside, cimiracemoside , and 14 known triterpene glycosides have been isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa). On the basis of spectral and chemical evidence, the structure of the new compound was elucidated to be 12beta-acetoxycimigenol-3-O-beta-D-xylopranoside, and the known compounds were identified to be 25-acetylcimigenol xyloside, cimigenol-3-O-beta-D-xylopyranoside, acetin, 27-deoxyacetin, cimicifugoside H-1, 23-O-acetylshengmanol 3-O-beta-D-xylopranoside, foetidinol-3-O-beta-xyloside, cimicifugoside H-2, 25-O-methylcimigenol xyloside, 21-hydroxycimigenol-3-O-beta-D-xylopyranoside, 24-epi-7,8-didehydrocimigenol-3-xyloside, cimidahurinine, cimidahurine and cimifugin. The compounds, , and showed weak antibacterial activities in the agar diffusion assay.

Anti-Bacterial Agents↗
PubMed2006

Phenolic glycosides from leaves of Hopiciopsis lobata.

A new phenolic glycoside, 6'-[(E)-2''-hydroxymethyl, 2''-butenoyl] arbutin (1), and two known phenolic glycosides, 6'-[(E)-4''-hydroxycinnamoyl] arbutin (2) and 6'-[(E)-3'',4''-dihydroxycinnamoyl] arbutin (3), were isolated from the leaves of Heliciopsis lobata (Merr.) Sleum. Their structures were elucidated by various spectroscopic methods including 2D NMR spectroscopy.

Arbutin↗
PubMedDate not supplied

New flavonol glycosides and new xanthone from Polygala japonica.

Three new flavonol glycosides and a new xanthone were isolated from Polygala japonica HOUTT. with eight known compounds. Their structures were identified as 1,7-dihydroxy-3,4-dimethoxy-xanthone (1), kaempferol-7,4'-dimethyl ether (2), physcion (3), guazijinxanthone (4), rhamnetin (5), polygalin A (6), 3,5,7-trihydroxy-4'-methoxy-flavone-3-O-beta-d-galactopyranoside (7), 3,5,3'-trihydoxy-7,4'-dimethoxy-flavone-3-O-beta-d-galactopyranoside (8), 3,5,3',4'-tetrahydroxy-7-methoxy-flavone-3-O-beta-d-galactopyranoside (9), 3,5,3',4'-tetrahydroxy-7-methoxy-flavone-3-O-beta-d-glucopyranoside (10), polygalin B (11), polygalin C (12). Among them, compound 4 is a new xanthone, and 6, 11 and 12 are new flavonol glycosides. Compounds 1, 4, 7 and 8 were tested for cytotoxic activity with MTT assays on five human tumor cell lines, K562, A549, PC-3M, HCT-8 and SHG-44. Compound 4 showed cytotoxic activity against all the five cell lines.

Antineoplastic Agents, Phytogenic↗
PubMedDate not supplied

A new acylated flavonol glycoside from Derris triofoliata.

A new acylated flavonol glycoside, kaempferol 3-O-[(6''''-feruloyl)-beta-D-glucopyranosyl-(1 --> 3)]-[alpha-L-rhamnopyranosyl-(1 --> 6)]-beta-D-glucopyranoside and two known cyclolignan glycosides, (+)-lyoniresinol-3alpha-O-beta-D-glucopyranoside and ( - )-lyoniresinol-3alpha-O-beta-D-glucopyranoside were isolated from n-BuOH extracts of the aerial parts of Derris triofoliata, their structures were determined from spectroscopic and chemical evidences.

Acylation↗
PubMed1999

Flavonoid glycosides from Thalictrum przewalskii.

A new flavonoid glycoside, 5,7-dihydroxy-4'-methoxyflavone-7-O-[6-O-(4-O-acetyl-alpha-L-rhamnosyl)-3-O-beta-D-glucosyl]-6-O-acetyl-beta-D-glucoside and three known flavonoid glycosides, 5,7-dihydroxy-4-methoxyflavone-7-0-[6-0-(4-0-acetyl-alpha-L-rhamnosyl)]-beta-D-glucoside, 3,5,7, 4'-tetrahydroxyflavonol-3-O-beta-D-glucoside and 5,7-dihydroxy-4'-methoxyflavone-7-O-(6-O-alphaL-rhamnosyl)-beta-D-glucoside were isolated from the whole plant of Thalictrum przewalskii. Their structures were determined on the basis of spectroscopic evidences.

Flavonoids↗
PubMed2001

New antifeedant triterpene glycosides from the Caribbean sponge Erylus formosus.

Two groups of antifeedant triterpene glycosides were identified from the Caribbean sponge Erylus formosus. The structure of formoside B, a novel N-acetyl amino derivative of the known penasterol tetrasaccharide formoside, was elucidated using NMR and mass spectral data. Four triterpene hexasaccharides and two triterpene trisaccharides, characterized by a 31-carbon aglycone, proved difficult to isolate and therefore only the structure of their aglycone was determined. Gas chromatographic analysis of derivatized saccharides from these mixtures established the carbohydrate content of these compounds. All of the triterpene glycosides isolated contributed to the chemical defenses of this sponge, although with differing activities.

Amino Sugars↗
PubMed1999

The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man.

Flavonoids are antioxidants present in plant foods. They occur mainly as glycosides, i.e. linked with various sugars. It is uncertain to what extent dietary flavonoid glycosides are absorbed from the gut. We investigated how the nature of the sugar group affected absorption of one major flavonoid, quercetin. Quercetin linked with glucose, i.e. quercetin glucoside and quercetin linked with rutinose, i.e. quercetin rutinoside, both occur widely in foods. When we fed these compounds to nine volunteers, the peak concentration of quercetin (Cmax) in plasma was 20 times higher and was reached (Tmax) more than ten times faster after intake of the glucoside (Cmax = 3.5+/-0.6 microM (mean +/- SE); Tmax < 0.5 h) than after the rutinoside (Cmax = 0.18+/-0.04 microM; Tmax = 6.0+/-1.2 h). The bioavailability of the rutinoside was only 20% of that of the glucoside. We suggest that quercetin glucoside is actively absorbed from the small intestine, whereas quercetin rutinoside is absorbed from the colon after deglycosylation. Absorption of other food components might also be enhanced by attachment of a glucose group.

Absorption↗
PubMed2004

Glycosidic monoterpenes from Linaria capraria.

During our systematic study on the species of genus Linaria (Scrophulariaceae) present in Italy, we examined the glycosidic fraction of Linaria capraria Moris et De Not., a species endemic of Tuscany archipelago. This fraction is particularly complex and we considered in this article only the medium polarity components. In accordance with previous studies, L. capraria shows acyl derivatives of antirrhinoside 1 as specific chemotaxonomic iridoidic markers. L. capraria exhibits a complex composition, with regard to iridoidic constituents, with several chromatographic problems to be resolved. We then isolated, besides the known antirrhinoside 1, two acyl derivatives of antirrhinoside, the 6'-O-senecioyl derivative, 2, and the 6'-O-angeloyl derivative, 3. In addition a glucoside of an acyclic monoterpene, 4, was also isolated, which may be correlated to the other monoterpenic glycosides isolated from other species of Scrophulariaceae.

Glycosides↗
PubMed2004

Pseudostichoposide B--new triterpene glycoside with unprecedent type of sulfatation from the deep-water North-Pacific Sea cucumber Pseudostichopus trachus.

New triterpene disulfated tetraoside, pseudostichoposide B (1) has been isolated from the sea cucumber Pseudostichopus trachus. The structure of this glycoside has been deduced by the extensive analysis of NMR and mass-spectra and chemical evidence. Except for a common sulfate group at C-4 of the first xylose residue, pseudostichoposide B contains an additional sulfate group at C-3 of quinovose residue in the carbohydrate chain, not earlier found in sea cucumber glycosides.

Animals↗
PubMed2005

Lipoxygenase inhibiting ethyl substituted glycoside from Symplocos racemosa.

Phytochemical investigation of Symplocos racemosa resulted in the isolation of a new ethyl substituted glycoside, 1-ethyl brachiose-3'-acetate (1) along with four known compounds ketochaulmoogric acid (2), nonaeicosanol (3), triacontyl palmitate (4) and methyl triacontanoate (5). The substitution of ethyl group on 1 was natural because during the course of extraction and purification ethanol was not used. The structural elucidation of the isolated compounds was based primarily on 1D- and 2D-NMR analysis, including COSY, HMQC, and HMBC correlations. The glycoside 1 and triacontyl palmitate (4) displayed the inhibitory potential against lipoxygenase and urease enzyme, respectively.

Glycosides↗
PubMed2006

Conversion of taxane glycosides to 10-deacetylbaccatin III.

10-Deacetylbaccatin III (10-DAB III) (2) was obtained by a series of treatment of a mixture of taxane glycosides (3, 4, and 5) without isolation before treatment. Since the taxane glycosides are isolated with paclitaxel from yew trees and can be found during the process of the production of paclitaxel, their conversion to 10-DAB III improves the total yield of paclitaxel (1) and docetaxel.

Chromatography, High Pressure Liquid↗
PubMed2006

A review: synthesis of aryl C-glycosides via the heck coupling reaction.

In this article, we focus on the synthesis of aryl C-glycosides via Heck coupling. It is organized based on the type of structures used in the assembly of the C-glycosides (also called C-nucleosides) with the following subsections: pyrimidine C-nucleosides, purine C-nucleosides, and monocyclic, bicyclic, and tetracyclic C-nucleosides. The reagents and conditions used for conducting the Heck coupling reactions are discussed. The subsequent conversion of the Heck products to the corresponding target molecules and the application of the target molecules are also described.

Chemistry↗
PubMed2006

In vitro degradation of the flavonol quercetin and of quercetin glycosides in the porcine hindgut.

The present study investigated the microbial degradation of the plant flavonol quercetin and its naturally occurring glycosides isoquercitrin and rutin in the porcine hindgut. The experiments were carried out with the semicontinuous colon-simulation technique. The fluid and particle phase of pig hindgut contents from freshly slaughtered animals were used for the in vitro incubations. Following a five-day equilibration period, quercetin, isoquercitrin or rutin were administered to fermentation vessels and their turnover rate was determined. None of the flavonols affected parameters of microbial fermentation like pH, redox potential or VFA production. The turnover rate for isoquercitrin was seven times higher than the turnover for the fermentation fluid. The turnover rates for quercetin and rutin were four and twofold higher than fluid turnover, respectively. After administration of isoquercitrin or rutin, their aglycone quercetin was detected as an intermediary metabolite. Under sterile conditions using autoclaved incubation fluids and hindgut contents, turnover rates for quercetin and rutin were still higher than the fluid turnover in the fermentation vessels. This indicates a certain chemical instability of the flavonols and/or adsorption to ingesta particles. Thus, flavonols are subjected to microbial metabolism in the porcine hindgut. The glycosidic structure strongly influences the rate of metabolism.

Adsorption↗
PubMed1967

Effects of cardiac glycosides on electrical activity in the isolated retina of the frog.

Ouabain added to physiological salt solutions bathing the isolated frog retina irreversibly abolishes the electrical response to light (the electroretinogram or ERG). The time course of abolition depends on the concentration of ouabain in the medium and the surface of the retina to which it is applied. When the glycoside is placed on the receptor surface, in 7 min the ERG is completely eliminated by 10(-4)M ouabain and more than 90% inhibited by 3 x 10(-5)M ouabain. The effect is slower at lower concentrations and when the solution is applied to the vitreous surface of the retina. The evidence suggests that abolition of the ERG by ouabain is due principally to inhibition of the active transport of sodium: (a) Structurally modified glycosides which are considerably less potent inhibitors of alkali cation-activated ATPase activity in preparations of frog retinal outer segments are also poorer inhibitors of electrical activity in isolated retinas. (b) Replacing much of the sodium in the medium bathing the retina by choline, Tris, or sucrose significantly protects the retina from ouabain. It is suggested that in a standard sodium environment essentially constant activity of the sodium pump is required to prevent rapid and irreversible change. The cellular sites most critically dependent on the sodium pump have not been identified.

Adenosine Triphosphate↗