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At least 1,387 records · Page 77Linked to original sources
PubMed2005

DPPH radical-scavenging effect of several phenylpropanoid compounds and their glycoside derivatives.

Eugenol, isoeugenol, caffeic acid, ferulic acid, isoferulic acid, estragole, trans-anethole, and paeonol are components of a Chinese herbal medicine used as a painkiller and stomachic. We investigated the potential role of these compounds as antioxidants. We studied the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging effect of these molecules, together with some glycoside derivatives, to ascertain their potential in reducing the levels of activated oxygen species in vivo. The DPPH radical-scavenging effects of eugenol, isoeugenol, and the glycoside derivatives of caffeic acid, ferulic acid, and isoferulic acid (SC(50)=8-28 microM) were similar to those of alpha-tocopherol, which was used as a positive control.

Antioxidants↗
PubMed2006

Synthesis and cosmetic whitening effect of glycosides derived from several phenylpropanoids.

Plant-derived phenylpropanoid compounds (4-ethyl-2-methoxyphenol, 2,6-dimethoxyphenol, 2,3-dimethoxyphenol, 3,4-dimethoxyphenol, 3,5-dimethoxyphenol, 3,4-dihydroxycinnamic acid, 4-hydroxy-3-methoxycinnamic acid, and 3-hydroxy-4-methoxycinnamic acid) were glycosidated to form glycoside compounds. We evaluated the effects of these compounds on the inhibition of tyrosinase and melanin synthesis and their cytotoxicity from the viewpoint of their use as whitening agents in cosmetics. Some compounds had more potent tyrosinase-inhibiting activity than commercial arbutin, which was used as a control, and showed no cytotoxicity at low concentration ranges.

Animals↗
PubMed2003

The application of liquid chromatography-electrospray ionization mass spectrometry and collision-induced dissociation in the structural characterization of acylated flavonol O-glycosides from the seeds of Carrichtera annua.

The flavonoid fraction from the seeds of Carrichtera annua was studied using high-performance liquid chromatography simultaneously coupled to a photodiode array detector (LC/UV-DAD) and a mass spectrometer equipped with an electrospray source (LC/ESI-MS). Collision-induced dissociation (CID) mass spectral data obtained off-line by nanospray (nano-ESI) analysis provided a wealth of complementary structural information, which was consistent with structures established by NMR or led to the proposal of base structures of the flavonol O-glycosides present in the Carrichtera annua seed extract. The flavonoid fraction was found to contain 12 structurally related flavonol O-glycosides. Eleven flavonoids, of which several were new compounds, were acylated with one or more benzoyl, feruloyl or sinapoyl groups. These acyl groups gave rise to characteristic product ions in the [M + H](+) and [M + Na](+) CID spectra as well as to radicalar acid-related product ions at high-energy collisional activation. In addition to the characterization of the acyl substituents, the mass spectral data allowed the identification of the aglycone, the determination of the base structure and the differentiation of several positional isomers.

Acylation↗
PubMed2005

Homolytic cleavage of the O-glycoside bond in carbohydrates: a steady-state radiolysis study.

The formation of products resulting from the O-glycoside bond cleavage following radiolysis of aqueous solutions of methyl-alpha-D-glucopyranoside (I), 3-O-methyl-alpha-D-glucopyranose (II), maltose, lactose, gentiobiose and cellobiose were studied. Radiation-induced destruction yields were also determined for dextran, laminarin and trimethylcelulose upon irradiation of their aqueous solutions. Oxygen, quinones and compounds capable of forming quinoid structures were found to inhibit radiation-induced homolytic destruction processes taking place in glycosides, di- and polysaccharides. The data obtained in this study enabled the authors to demonstrate an important role played by the fragmentation reaction of C-2 radicals which were generated from the starting substances in the formation of final radiolysis products.

Binding Sites↗
PubMed1994

(S)-linalyl, 2-phenylethyl, and benzyl disaccharide glycosides isolated as aroma precursors from oolong tea leaves.

Three glycosides, 6-O-beta-D-xylopyranosyl-beta-D-glucopyranosides (beta-primeverosides) of the aroma constituents, linalool, 2-phenylethanol, and benzyl alcohol, were isolated as aroma precursors from the tea leaves (Camellia sinensis var. sinensis cv. Shuixian and Maoxie, cultivars for oolong tea). The isolation was guided by acid or enzymatic hydrolysis, and subsequent GC and GC-MS analyses. The linalyl glycoside is the first example of naturally occurring (S)-linalyl beta-primeveroside.

Benzyl Alcohols↗
PubMed1996

Isolation and identification of two new diterpene glycosides from Nicotiana tabacum.

Two new diterpene glycosides containing 20-hydroxygeranyllinalool were isolated and identified from Nicotiana tabacum. These compounds consisted of five molecules of glucose and/or rhamnose. The locations of the aglycone and glycosides in the molecules were determined by 2D-NMR with the HMBC technique. The structures were (6E,10E,14Z)-20-hydroxygeranyllinalyl-3-O- [alpha-L-rhamnopyranosyl (1 --> 4)]-beta-D-glucopyranoside-20-O- [beta-D-glucopyranosyl (1 --> 2)]-[alpha-L-rhamnopyranosyl (1 --> 6)]-beta-D- glucopyranoside and (6E,10E,14Z)-20-hydroxygeranyllinalyl-3-O- [alpha-L-rhamnopyranosyl (1 --> 4)]-beta-D-glycopyranoside-20-O- [alpha-L-rhamnopyranosyl (1 --> 4)]-[alpha-L-rhamnopyranosyl (1 --> 6)]-beta-D- glucopyranoside.

Carbohydrate Sequence↗
PubMed2003

New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit.

Potent antioxidative hydroxyflavanones were produced with Aspergillus saitoi from hesperidin or naringin, which are flavanone glycosides in citrus fruit with weak antioxidative activity. The hydroxyflavanone produced from hesperidin was identified as 8-hydroxyhesperetin (8-HHE), a novel substance, and those from naringin were identified as carthamidin (6-hydroxynaringenin) and isocarthamidin (8-hydroxynaringenin) by FAB-MS, 1H-NMR and 13C-NMR analyses. The antioxidative activity of these hydroxyflavanones was examined by using the free radical-scavenging system of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the methyl linoleate oxidation system. The hydroxyflavanones (8-HHE, carthamidin, and isocarthamidin) exhibited stronger activity than the flavanone glycosides (hesperidin or naringin) and their aglycones (hesperetin or naringenin). The activity of 8-HHE and isocarthamidin was comparable to that of alpha-tocopherol, and that of carthamidin was weaker than that of isocarthamidin. The hydroxyflavanones, which were hydroxylated on A ring of flavanone by Aspergillus saitoi, were obtained as potent antioxidants.

Antioxidants↗
PubMedDate not supplied

Behavioral effect of herbal glycoside in the forced swimming test.

We investigated the behavioral effects of Chinese herbal medicines in the forced swimming test. One of these medicines, Kami-shoyo-san, induced an antidepressive climbing behavior in mice. An effective substance detected to be an O-linked glycoside with the sugar chain structure GalNAc alpha 1-3GalNAc was separated. The behavioral effect was dose-dependently decreased by the dopamine 2 antagonist sulpiride, but not by the dopamine 1 antagonist SCH-233960. Investigated Chinese herbal medicines, including Kami-shoyo-san, have been used for human depression. These facts suggest that glycoside is one of the antidepressant-like substances of Chinese herbal medicines.

Animals↗
PubMedDate not supplied

A glycoside of Nicotina tabacum affects mouse dopaminergic behavior.

Climbing in the forced swimming test is considered a dopaminergic-specific behavior. A substance of Nicotina tabacum affecting dopamine neuronal activity was investigated using the mouse behavioral system. The substance was found to be a glycoside with the peripheral sugar chain structures Fuc alpha 1-2Gal, Gal beta 1-4GlcNAc and GalNAc alpha 1-3GalNAc and with basic polymannoses. The glycoside dose-dependently increased behavior via D2 neuronal activity, but not D1 activity. This suggests that smoking can affect human brain function not only via the nicotinic cholinergic neuron, but also via the D2 neuron.

Animals↗
PubMedDate not supplied

Effect of 2'-deoxyguanosine oxidation at C8 position on N-glycosidic bond stability.

The influence of 2'-deoxyguanosine (dG) oxidation at the C-8 position on N-glycosidic bond stability was investigated. A kinetic analysis of dG and 8-oxo-2'-deoxyguanosine (8-oxodG) depurination reactions was carried out in water solutions at pH ranging from 2 to 7.4 and temperature of 100 degrees C. The results indicate that N-glycosidic bond of 8-oxodG is significantly more stable in comparison with dG at any pH applied. At pH 5.1 hydrolysis rate of dG is 4.5-fold higher than that for 8-oxodG. The chemical stability of the modified nucleoside in oxidatively damaged DNA is one of important factors contributing to its mutagenic potential. Results of our experiments indicate that 8-oxodG, potentially mutagenic and carcinogenic nucleoside, is hardly susceptible to spontaneous depurination and its removal from cellular DNA depends mostly on the activity of DNA repair enzymes.

Deoxyguanosine↗
PubMedDate not supplied

Isoangoroside C, a phenylpropanoid glycoside from Scrophularia scorodonia roots.

A new phenylpropanoid glycoside isoangoroside C was isolated from the roots of Scrophularia scorodonia. Its structure was determined on the basis of spectral data as: 3-hydroxy-4-methoxy-beta-phenylethoxy-O-alpha-L-arabinopyranosy l-(1-->6)alpha L-rhamnopyranosyl-(1-->3)-4-O-Z-feruloyl-beta-D-glucopyranoside. Additionally, one known phenylpropanoid, angoroside C, and five known iridoid glycosides, harpagoside, bartsioside, 8-O-acetyl-harpagide, aucuboside and harpagide were isolated and identified.

Carbohydrate Sequence↗
PubMedDate not supplied

The first glycosides isolated from propolis: diterpene rhamnosides.

Two diterpene glycosides, ent-8(17)-labden-15-O-alpha-L-rhamnoside and ent-8(17)-labden-15-O-(3'-O-acetyl)-alpha-L-rhamnoside (new natural compounds) were isolated from propolis from El Salvador. The compounds showed significant antibacterial activity and moderate toxicity to Artemia salina nauplii. These are the first glycosides reported in bee glue.

Animals↗
PubMedDate not supplied

Paeonicluside, a new salicylic glycoside from the Greek endemic species Paeonia clusii.

A new glycoside of salicylic aldehyde, paeonicluside, was isolated from the roots of the Greek endemic species Paeonia clusii subsp. clusii and identified as alpha-L-arabinopyranosyl-(1-->6)-O-beta-D-glucopyranoside of salicylic aldehyde (1). In addition, one characteristic monoterpene and two monoterpene glycosides were identified as paeoniflorigenone, paeoniflorin and benzoyl paeoniflorin, respectively. The structure of 1 was elucidated on the basis of its spectroscopic data and chemical correlation. It is the first time that a derivative of salicylic aldehyde is isolated from the well-studied Paeonia genus.

Bridged-Ring Compounds↗
PubMedDate not supplied

Phenylethanoid glycosides from Phlomis integrifolia Hub.-Mor.

Two new phenylethanoid glycosides integrifoliosides A (2) and B (3), along with a known phenylethanoid glycoside alyssonoside (1) and a flavone glucoside chrysoeriol-7-O-beta-D-glucopyranoside (4) were isolated from the aerial parts of Phlomis integrifolia. The structures of the new compounds were identified as 3,4-dihydroxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-4-O-feruloyl-beta-D-glucopyranoside (2) and 3-hydroxy-4-methoxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-4-O-feruloyl-beta-D-glucopyranoside (3), on the basis of spectroscopic (UV, IR, 1D- and 2D-NMR, and HR-FABMS) methods.

Carbohydrate Sequence↗
PubMedDate not supplied

Ionone, iridoid and phenylethanoid glycosides from Ajuga salicifolia.

From the aerial parts of Ajuga salicifolia (L.) Schreber, a new ionone glycoside (3beta-hydroxy-7,8-dihydro-4-oxo-beta-ionol-9-O-beta-D-glucopyranoside) was isolated, along with the known compounds, corchoionoside C, 8-O-acetylmioporoside, ajugol, harpagide, 8-O-acetylharpagide, lavandulifolioside and leonosides A and B. This is the first report of the occurrence of ionone glycosides and 8-O-acetylmioporoside in Ajuga species. Ajugol, lavandulifolioside, leonoside A and B were isolated for the first time from Ajuga salicifolia. The structures were elucidated by means of 1D-, 2D-NMR spectroscopy, and HR-MALDI mass spectrometry.

Ajuga↗
PubMed1995

Cardiac glycosides. Drug interactions of clinical significance.

Several commonly coadministered drugs interfere significantly with the pharmacokinetics or pharmacodynamics of cardiac glycosides. Only a few of these interactions (e.g. amiodarone, propafenone, quinidine) take place consistently, and although their extent may vary in individual patients, digitalis dosage adjustments should be made to avoid underdigitalization or toxicity. In other instances the appearance of clinically significant interactions depends on individual pharmacokinetic/metabolic characteristics (e.g. erythromycin, tetracycline), and the result cannot be anticipated on clinical grounds. Some interactions are controversial, having not been confirmed by all studies; others have been shown only in healthy volunteers but lack the definition of their relevance in the context of disease states. In view of the possible impact on the individual patient, close clinical monitoring (which may be supplemented with evaluation of digitalis plasma concentration) is recommended when prescribing cardiac glycosides with other therapeutic agents for which the possibility of an interaction has been reported.

Animals↗
PubMed1977

Elimination of cardiac glycosides through hemofiltration.

Elimination of three different cardiac glycosides by hemofiltration was investigated using the flat bed RP-6 (Rhône-Poulenc, Paris). At a filtration rate of 59 +/- 9 ml/min the mean clearance of 3-H-g-strophanthin was 54.9 +/- 10.4, that of a 3-H-digoxin and unlabelled digoxin 36.7 +/- 6.6 and that of digitoxin 4.6 +/- 2.8 ml/min. It is concluded from these results that hemofiltration is able to eliminate more than 50% of the amount excreted during the same period of time by normal kidneys. Elimination of cardiac glycosides by continuous hemofiltration is high enough to justify its use in digitalis intoxication, particularly because of the excellent control of electrolyte balance with this new method of detoxification.

Cardiac Glycosides↗
PubMed1987

Demonstration and characterization of two classes of cardiac glycoside binding sites to rat heart membrane preparations using quantitative computer modeling.

Cardiac glycoside binding to rat heart membrane preparations was measured by rapid filtration technique. The binding data were analyzed using quantitative computer analysis. The experimental results using [3H]-ouabain as the labeled ligand were consistent with a model in which cardiac glycoside specific binding occurs at two independent classes of sites. The high affinity sites were characterized by a dissociation constants of 40 nM, 50 nM, and 61 nM for ouabain, digoxin and digitoxin, respectively, with a binding capacity of 1.3 pmoles/mg protein. The lower affinity sites for ouabain were characterized by dissociation constants of 2.3 microM, 67 nM and 71 nM for ouabain, digoxin and digitoxin, respectively, with a binding capacity of 3 pmoles/mg protein. Potassium ions inhibit [3H]-ouabain binding in a dose dependent manner with an IC50 of 500 microM. Quantitative computer modelling indicated that potassium inhibits ouabain binding at both binding sites.

Animals↗