Showing papers on "Glucoside published in 2004"
TL;DR: The flavonoid composition of broccoli inflorescences has been studied by LC/UV-DAD/ESI-MSn and several less complex glucosides based on the same aglycones have been identified.
211 citations
TL;DR: The major flavonoids in the white florets of chamomile were rapidly purified using a combination of polyamide solid-phase extraction and preparative HPLC to identify mono-acetyl/mono-malonyl and caffeoyl derivatives of Ap-7-Glc, which have not previously been reported in any plant species.
166 citations
TL;DR: A chemical study of grape pomace, from the red Sicilian cultivar ''Nerello Mascalese', has been carried out as discussed by the authors, where the methanolic extract was further fractionated and analysed by HPLC-UV-DAD and HPLC−MS-ESI, allowing identification of 16 flavonols or flavonol glucosides ( 1 - 16), the flavan-3-ols catechin ( 17 ) and epicatechin ( 18 ), as well as their gallate esters 19 and 20, 10 anthocyanins
111 citations
TL;DR: Bioassay-guided fractionation of the ethanol extract of Ficus racemosa resulted in the identification of a new compound (rel)-4,6-dihydroxy-5-[3-methyl-(E)-propenoic acid-3-yl]-7-beta-glucopyranosyl (racemosic acid), which demonstrated a strong antioxidant activity to scavenge ABTS free radical cations.
Abstract: Bioassay-guided fractionation of the ethanol extract of Ficus racemosa resulted in the identification of a new compound (rel)-4,6-dihydroxy-5-[3-methyl-(E)-propenoic acid-3-yl]-7-beta-glucopyranosyl-[2alpha,3beta-dihydrobenzofuran]-(3,2: b)-[4alpha,5beta-dihydroxy-6alpha-hydroxymethyltetrahydropyran] (racemosic acid). Racemosic acid showed potent inhibitory activity against COX-1 and 5-LOX in vitro with IC50 values of 90 and 18 microM, respectively. Racemosic acid also demonstrated a strong antioxidant activity to scavenge ABTS free radical cations with an IC50 value of 19 microM. In addition, cytotoxic effects of the extracts of F. racemosa were investigated in vitro using the ATP-based luminescence assay and results showed no cytotoxicity on the cell lines skin fibroblasts (1BR3), human Caucasian hepatocyte carcinoma (Hep G2) and human Caucasian promyelocytic leukaemia (HL-60). Bergenin was also isolated from the same active fraction.
102 citations
TL;DR: The results suggest that the anti-inflammatory and antinociceptive effects of syringin after oral administration may be attributed to its in vivo transformation to sinapyl alcohol.
Abstract: In the present study, syringin, isolated by activity-guided fractionation of the ethyl acetate (EtOAc) extracts of the stem bark of Magnolia sieboldii, and sinapyl alcohol, the hydrolysate of syringin, were evaluated for anti-inflammatory and antinociceptive activities. Sinapyl alcohol (20, 30 mg/kg/day, p. o.) inhibited increased vascular permeability by acetic acid in mice and reduced acute paw edema by carrageenan in rats more so than syringin. When analgesic activity was measured using the acetic acid-induced writhing test and the hot plate test, sinapyl alcohol was much more potent than syringin in a mouse model. In addition, sinapyl alcohol more potently inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO), prostaglandin E2 (PGE2), and tumor necrosis factor (TNF)-alpha production by macrophages than syringin. Consistent with these observations, the expression levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 was reduced by sinapyl alcohol in a concentration-dependent manner. These results suggest that the anti-inflammatory and antinociceptive effects of syringin after oral administration may be attributed to its in vivo transformation to sinapyl alcohol.
89 citations
TL;DR: Four new abscisic acid related compounds (1-4) were isolated from the antioxidative ethanol extract of prunes and the antioxidant activities of these isolated compounds were evaluated on the basis of oxygen radical absorbance capacity (ORAC).
Abstract: Four new abscisic acid related compounds (1−4), together with (+)-abscisic acid (5), (+)-β-d-glucopyranosyl abscisate (6), (6S,9R)-roseoside (7), and two lignan glucosides ((+)-pinoresinol mono-β-d-glucopyranoside (8) and 3-(β-d-glucopyranosyloxymethyl)-2- (4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (9)) were isolated from the antioxidative ethanol extract of prunes (Prunus domestica L.). The structures of 1−4 were elucidated on the basis of NMR and MS spectrometric data to be rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (1), rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid 3‘-O-β-d-glucopyranoside (2), rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (3), and rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxabicyclo[3,2,1]- oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (4). The antioxidant activ...
82 citations
TL;DR: In this paper, the first report of quercetin 3-O-β-d -apiofuranosyl-(1‴→∼2″)-O-[a- l -rhamnopyranosyl(1⁗→6″)]-∼3- d -galactopyranoide-3′,4′-dimethyl ether All structures were elucidated by chemical and spectroscopic methods, namely NMR (1H, 13C, COSY, HMQC, HMBC), mass data (
69 citations
TL;DR: 2,4-Dihydropyrazole glucosides 3a-3c were prepared and tested for their antitumor activity and shows an in vitro IC(50) value of 16.4 muM against proliferation of the human promyelotic leukemia (HL60) cell line.
Abstract: 2,4-Dihydropyrazole glucosides 3a-3c were prepared and tested for theirantitumor activity. The structures of these compounds were established by 1H and 13C-NMR spectroscopy. Glucoside 3b shows an in vitro IC50 value of 16.4 μM againstproliferation of the human promyelotic leukemia (HL60) cell line.
67 citations
TL;DR: Results suggested that 2-hydroxy-3-methoxyphenyl)propane-1,3-diol and 3-O-beta-d-glucopyranosyl-2-(4-hydroxyphenol)propanol showed an appreciable activity in both assay systems.
Abstract: In the course of our study on the isolation and structure determination of constituents in tropical plants, we focused on Peucedanum japonicum Thunb., belonging to the family Umbelliferae. In this study, a new C(13) norisoprenoid glucoside, (3S)-O-beta-d-glucopyranosyl-6-[3-oxo-(2S)-butenylidenyl]-1,1,5-trimethylcyclohexan-(5R)-ol (1), and two new phenylpropanoid glucosides, 3-(2-O-beta-d-glucopyranosyl-4-hydroxyphenyl)propanoic acid (3) and methyl 3-(2-O-beta-d-glucopyranosyl-4-hydroxyphenyl)propanoate (4), were isolated from the n-butanol soluble fraction of this plant's leaves, together with five known compounds. The structures of these compounds were determined on the basis of spectroscopic evidence. In addition, all isolated compounds were examined for scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical and inhibitory activity against mushroom tyrosinase. These results suggested that 2-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol (7) and 3-O-beta-d-glucopyranosyl-2-(4-hydroxy-3-methoxyphenyl)propanol (8) showed an appreciable activity in both assay systems.
62 citations
TL;DR: Experiments in volunteers have demonstrated that this ethyl glucoside results from dietary exposure to the compound, which is present in beverages such as rice wine and sake, rather than representing a new route for the metabolism of ethanol by humans.
Abstract: Metabonomic screening of human urine samples using 1H NMR spectroscopy has revealed the presence of signals resulting from the excretion of ethyl glucoside. Experiments in volunteers have demonstrated that this ethyl glucoside results from dietary exposure to the compound, which is present in beverages such as rice wine and sake, rather than representing a new route for the metabolism of ethanol by humans. The limited studies undertaken in volunteers indicate that ethyl glucoside has a longer biological half life than ethanol itself. The potential problems associated with using this glucoside metabolite as a marker of ethanol consumption are considered.
60 citations
TL;DR: LC-NMR as well as off-line two-dimensional NMR were used to obtain further structural information about the main isoflavones in extracts of leaves of T. pratense L. are biochanin A and formononetin, and two glucoside malonate isomers of each of them have quite different structures.
Abstract: Previous studies revealed that the main isoflavones in extracts of leaves of T. pratense L. are biochanin A and formononetin, their 7-O-glucosides, and two glucoside malonate isomers of each of them. Since LC-MS(/MS) did not provide sufficient information to distinguish the glucoside malonate isomers, in the present paper LC-NMR as well as off-line two-dimensional NMR were used to obtain further structural information. Matrix solid-phase dispersion (MSPD) was applied to obtain sufficiently high analyte concentrations to perform LC-NMR. Stop-flow reversed-phase LC-NMR was performed using a gradient of deuterated water and deuterated acetonitrile. Offline COSY and NOESY experiments were carried out to determine the positions of the glucose moiety on the flavonoid aglycone, and of the malonate moiety on the glucose. Based on the fragmentation patterns in MS/MS and the NMR spectra, the two formononetin glucoside malonate isomers were identified as 7-O-beta-D-glucoside 6"-O-malonate and 7-O-beta-D-glucoside 4"-O-malonate; i.e. they only differ in the substitution position of the malonate group on the glucoside ring. The biochanin A glucoside malonate isomers, however, have quite different structures. The main and later eluting isomer is biochanin A 7-O-beta-D-glucoside 6"-O-malonate, and the minor and earlier eluting isomer is 5-hydroxy-7-methoxyisoflavone 4'-O-beta-D-glucoside 4"-O-malonate: the positions of the methoxy group and the glucoside 6"-O-malonate group on the flavonoid skeleton are interchanged.
TL;DR: In this article, the presence of β-D-glucosides of these compounds was investigated, in order to determine if these compounds are derived from glucosides or if they are formed during the curing process via different pathways.
TL;DR: In this article, the β- d -glucopyranosides of all four stereoisomers of 3-methyl-4-hydroxyoctanoic acid have been prepared.
TL;DR: Results indicate that Q4'G, even though it has a low chelating activity, can act as a powerful antioxidant on iron ion driven lipid peroxidation in the intestinal mucosa.
Abstract: Quercetin is a typical antioxidative flavonoid found in vegetables, which is more commonly present as its glucosides, quercetin-3-glucoside (Q3G) and quercetin-4'-glucoside (Q4'G). The main aim of this study was to estimate the antioxidant activity of Q3G and Q4'G on iron ion-driven lipid peroxidation of the gastrointestinal mucosa. Q4'G markedly suppressed the lipid peroxidation when rat gastrointestinal mucosa homogenates were incubated with Fe(NO3)3 and ascorbic acid. Its effectiveness was greater as compared to that of Q3G and comparable to that of quercetin aglycone. Furthermore, Q4'G yielded higher amounts of quercetin aglycone than Q3G on incubation with the homogenates. However, Q4'G showed a lower chelating activity in comparison to Q3G. These results indicate that Q4'G, even though it has a low chelating activity, because of its efficient conversion to antioxidative aglycone on exposure to the mucosa, can act as a powerful antioxidant on iron ion driven lipid peroxidation in the intestinal mucosa. Thus, vegetables rich in Q4'G, such as onion, are likely to serve as favorable antioxidant sources for suppressing iron-induced oxidative stress in the intestinal tract.
TL;DR: Pongamia pinnata fruits afforded three new furanoflavonoid glucosides, pongamosides A-C (1-3), and a new flavonol glucoside, pongsamoside D (4).
TL;DR: Isolates were evaluated for antioxidant activities and most of the tested compounds were found to be potent in DPPH free radical scavenging and superoxide anion scavenging assays.
Abstract: Five caffeic acid derivatives; methyl ester of caffeoylglycolic acid (1), dimethyl ester of caffeoyltartaric acid (2), dimethyl ester of caffeoyltartronic acid (3), monomethyl ester of caffeoyltartronic acid (4), methyl ester of caffeic acid (5), and some other secondary metabolites including; quercetin, quercetin 3-O-β-D-glucuronide methyl ester, kaempferol, 3,5,7,4′-O-tetramethylkaempferol, β-sitosterol glucoside, 2α-hydroxyursolic acid and 2,24-dihydroxyursolic acid, have been isolated and characterized. All the isolated compounds were characterized with the help of NMR spectroscopy and mass spectrometry. Structure of compound3 was also confirmed by a single X-ray crystallographic technique. Isolates were evaluated for antioxidant activities and most of the tested compounds were found to be potent in DPPH free radical scavenging (IC50 = 4.56–14.17 μg/mL) and superoxide anion scavenging (IC50= 0.58–7.39 μg/mL) assays.
TL;DR: The capability of the skin to metabolize the prodrug in a slow and prolonged manner is shown, making this gluco-conjugated vitamin E an excellent candidate for continuous reinforcement of antioxidants in the skin.
TL;DR: Tests on isolated uterine smooth muscle from rats showed that the whole extract stimulated a direct contractile response and induced a state of continuous contractility of the uterus once all additives had been removed from the organ bath.
TL;DR: The results suggest that BG and CA may contribute to relieving the tension in M-rats caused by ether stress.
Abstract: To investigate the effectiveness of benzyl β-D-glucopyranoside (BG) and chlorogenic acid (CA), the constituents of the fruit of Prunus mume, for relieving tension in experimental menopausal model rats (M-rats) caused by ether stress, the effects of BG and CA on adrenocorticotropic hormone (ACTH) and catecholamine (adrenaline, noradrenaline, and dopamine) levels were examined in the plasma of M-rats. Caffeic acid, quinic acid, and rosmarinic acid, which are compounds structurally related to CA, were also examined. BG obviously recovered catecholamine levels decreased by ether stress and increased dopamine to high levels. On the other hand, CA significantly decreased the ACTH level increased by ether stress and showed the greatest effect of all compounds. These results suggest that BG and CA may contribute to relieving the tension in M-rats caused by ether stress.
TL;DR: Two new lignan glucosides were isolated from the stem of Strychnos vanprukii and exhibited antioxidant activity and the structures were elucidated on the basis of their spectroscopic data.
TL;DR: In this article, a new acyl flavonoid apigenin-7-O-b-D-(6"-trans-p -coumaroyl)-3"-O-acetyl glucopyranoside was also isolated.
Abstract: Phytochemical study of Acanthus arboreus resulted in the isolation of three novel alkaloids: 6-hydroxy-benzoxazolinone, 4-hydroxyacanthamine and acanthaminoside. In addition, a new acyl flavonoid apigenin-7-O-b-D-(6"-trans-p -coumaroyl)-3"-O-acetyl glucopyranoside was also isolated. The known compounds were identified as apigenin, apigenin-7- O-b-D-(6"-trans-p-coumaroyl) -glucoside, vanillic acid, lupeol, stigmasterol and sitosterol glucoside. The structures were determined by physical, chemical and spectral techniques.
TL;DR: A new triterpenoid, 2alpha,3alpha,24-trihydroxyurs-12-en- 28-oic acid-28-O-beta-D-glucopyranosyl ester is isolated from the leaves of Prunus serrulata var.
Abstract: A new triterpenoid, 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (4) along with four known triterpenoids, ursolic acid (1), 2alpha-hydroxyursolic acid (2), 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid (3), and 2alpha,3alpha,19alpha,24-tetrahydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (5), were isolated from the leaves of Prunus serrulata var. spontanea (Rosaceae). Compounds 3-5 showed ONOO(-) scavenging activity, whereas compounds 1 and 2 were virtually inactive.
TL;DR: Spinoside, new coumaroyl flavone glycoside was isolated from then-butanol fraction of the mathanolic extract of the whole plant of Amaranthus spinosus and assigned the structure 7-p-cou maroyl apigenin4-O-β-D-glucopyranoside on the basis of spectroscopic techniques including 1D and 2D NMR spectroscopy.
Abstract: Spinoside, new coumaroyl flavone glycoside was isolated from then-butanol fraction of the mathanolic extract of the whole plant ofAmaranthus spinosus and assigned the structure 7-p-coumaroyl apigenin4-O-β-D-glucopyranoside (1) on the basis of spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition α- xylofuranosyl uracil (2), β-D-ribofuranosyl adenine (3) and β-sitosterol glucoside (4) have also been isolated for the first time from this species.
TL;DR: The antioxidant effect of aqueous methanolic herb extracts of Serratula coronata, S. wolffii and S. tinctoria was investigated using both enzyme-dependent and enzyme-independent systems and the extracts displayed concentration-dependent inhibition of lipid peroxidation.
TL;DR: Five new phenolic glycosides were isolated from the whole plants of Pyrola japonica (Pyrolaceae), together with androsin, (-)-syringaresinol glucoside, homoarbutin, pirolatin, hyperin, monotropein and chimaphilin.
Abstract: Five new phenolic glycosides, 2-β-D-glucopyranosyloxy-5-hydroxyphenylacetic acid methyl ester (4), 4-hydroxy-2-[3-hydroxy-3-methylbutyl]-5-methylphenyl β-D-glucopyranoside (5), 4-hydroxy-2-[(E)-4-hydroxy-3-methyl-2-butenyl]-5-methylphenyl β-D-glucopyranoside (7), 4-hydroxy-2-[(2E,6Z)-8-β-D-glucopyranosyloxy-3,7-dimethylocta-2,6-dien-1-yl]-5-methylphenyl β-D-glucopyranoside (8), and 2,7-dimethyl-1,4-dihydronaphthalene-5,8-diol 5-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranoside (10), were isolated from the whole plants of Pyrola japonica (Pyrolaceae), together with androsin, (−)-syringaresinol glucoside, homoarbutin, pirolatin, hyperin, monotropein and chimaphilin.
TL;DR: Four ent-kaurenoic acid derivatives were isolated together with five known compounds from the 50% aqueous acetone extract of the aerial parts of Mikania hirsutissima DC for proliferative activity toward peripheral blood mononuclear cells (hPBMC).
Journal Article•
TL;DR: In this article, the effect of various pomace-contacting (maceration) methods on the concentrations of cis-and trans-resveratrol and resveratral glucoside isomers were investigated in Vitis vinifera L. cv. grape musts during alcoholic fermentation.
Abstract: The effect of various pomace-contacting (maceration) methods on the concentrations of cis - and trans -resveratrol and resveratrol glucoside isomers were investigated in Vitis vinifera L. cv. Cabernet Sauvignon grape musts during alcoholic fermentation. Compared to a classical red wine vinification (control), carbonic maceration resulted in no detectable quantities of all four forms of resveratrol throughout fermentation and pressing. Prefermentation cold-soaking significantly increased ( p trans -resveratrol glucoside concentration and slightly less extraction of cis -resveratrol glucoside. Free resveratrol was absent in the must heated prior to fermentation, while the level of resveratrol glucosides significantly increased ( p
TL;DR: In this article, β-selective glucosylations of glycosyl acceptors having a primary hydroxy group with a 6-nitro-2-benzothiazolyl α-glucoside donor 3α proceeded smoothly in the presence of a catalytic amount...
Abstract: Highly β-selective glucosylations of glycosyl acceptors having a primary hydroxy group with a 6-nitro-2-benzothiazolyl α-glucoside donor 3α proceeded smoothly in the presence of a catalytic amount ...
TL;DR: In this paper, two pyranoid δ-sugar amino acids were prepared from the common per-benzylated β-C-vinyl glucoside and easily oligomerised using solution-phase coupling methodology.
TL;DR: The cloning strategy took full advantage of the specific conservation of a sequence (–Tyr–Phe–Gly–Asn–Cys–, termed motif 2) in the anthocyanin-specific members of the versatile acyltransferase (VAT) family to suggest that Vh3MaT1 and Lp3 MaT1 should serve as useful biocatalysts for the malonylation of quercetin 3- O -glucoside
Abstract: Complementary DNAs coding for two flavonol 3- O -glucoside malonyltransferases, Vh3MaT1 and Lp3MaT1 , were cloned from flowers of Verbena hybrida and Lamium purpureum , respectively, expressed in Escherichia coli cells, and functionally characterized. The cloning strategy took full advantage of the specific conservation of a sequence (–Tyr–Phe–Gly–Asn–Cys–, termed motif 2) in the anthocyanin-specific members of the versatile acyltransferase (VAT) family. Both of the expressed proteins, Vh3MaT1 and Lp3MaT1, effectively catalyzed the regiospecific transfer of the malonyl group from malonyl-CoA to the 6″-hydroxyl group of quercetin 3- O -glucoside and were highly specific for these acyl donor and acceptor. Therefore, these enzymes are malonyl-CoA:flavonol 3- O -glucoside-6″- O -malonyltransferases. Kinetic parameters were determined at pH 7.0 and 30 °C as follows: for Vh3MaT1, k cat , 2.9 s −1 ; k cat / K m for quercetin 3- O -glucoside, 17 s −1 mM −1 ; and k cat / K m for malonyl-CoA, 930 s −1 mM −1 ; for Lp3MaT1, k cat , 9.0 s −1 ; k cat / K m for quercetin 3- O -glucoside, 28 s −1 mM −1 ; and k cat / K m for malonyl-CoA, 360 s −1 mM −1 . These results suggested that Vh3MaT1 and Lp3MaT1 should serve as useful biocatalysts for the malonylation of quercetin 3- O -glucoside to control the bioactivities and pharmacokinetics of the flavonoid. The results also show that VAT members having motif 2 are not restricted to “anthocyanin” acyltransferases but should include an extended class of enzymes, i.e. “flavonoid glucoside” acyltransferases.