Showing papers on "Glucoside published in 2003"
Patent•
15 May 2003TL;DR: In this article, an SGLT2 inhibiting compound is provided having the formula having the chemical structure, and a method is also provided for treating diabetes and related diseases employing an sGLT 2 inhibiting amount of the above compound alone or in combination with another antidiabetic agent or other therapeutic agent.
Abstract: An SGLT2 inhibiting compound is provided having the formula[Chemical structure] A method is also provided for treating diabetes and related diseases employing an SGLT2 inhibiting amount of the above compound alone or in combination with another antidiabetic agent or other therapeutic agent.
327 citations
TL;DR: The apparent bioavailability of genistein and daidzein is not different when consumed as either aglycone or glucoside by American women, probably because of the metabolic action of intestinal bacteria during the long intestinal transit time of glucosides.
307 citations
TL;DR: The mechanism of absorption of quercetin-4'-glucoside involves both an interaction with SGLT1 and luminal hydrolysis by LPH, whereas quercETin-3-glucOSide appears to be absorbed only following hydrolytic action of LPH.
295 citations
TL;DR: Catharanthus roseus cell suspension cultures converted exogenously supplied curcumin to a series of glucosides, none of which has been found in nature so far, which were dependent on culture stage of the cells and medium sucrose concentration.
216 citations
TL;DR: A HPLC method was developed for the analysis of secoisolariciresinol diglucoside (SDG) and hydroxycinnamic acid glucosides in milled defatted flaxseed flour and was found to be easy, fast, and with good repeatability.
164 citations
Patent•
23 Dec 2003TL;DR: In this paper, a method for the production of C-aryl glucoside SGLT2 inhibitors useful for the treatment of diabetes and related diseases is presented. But this method requires the use of amino acid complex forming reagents.
Abstract: Method for the production of C-aryl glucoside SGLT2 inhibitors useful for the treatment of diabetes and related diseases. and intermediates thereof. The C-aryl glucosides may be complexed with amino acid complex forming reagents.
150 citations
TL;DR: Both luteolin and oleanolic acid have an inhibitory effect on postprandial blood glucose increase in diabetic rats, and thus they may be a useful food supplement for the prevention of diabetes.
Abstract: Olive (Olea europaea L.) is recognized as a folk medicine for diabetes in Europe. The inhibitory action of an ethanol extract of olive leaves (OEE) on the activities of human amylases was examined in vitro. OEE inhibited the activities of α-amylases from human saliva and pancreas with IC50 values of 4.0 and 0.02 mg/ml, respectively. Two anti-α-amylase components were purified from a 50% ethanol soluble fraction of OEE using Sephadex LH-20 column chromatography. One was identified as luteolin-7-O-β glucoside and the other as luteolin-4′-O-β glucoside. The 50% ethanol insoluble fraction of OEE was dissolved in 98% ethanol and fractionated using Cosmosil C18-OPN column chromatography. The anti-α-amylase component purified by this chromatography was identified as oleanolic acid. Both luteolin and oleanolic acid have an inhibitory effect on postprandial blood glucose increase in diabetic rats. Olive leaves suppressed the elevation of blood glucose after oral administration of starch in borderline volunteers (fasting blood glucose: 110–140 mg/dl), and thus they may be a useful food supplement for the prevention of diabetes.
110 citations
TL;DR: This is the first report on the enzymatic preparation of minor saponins, ginsenosides Rg(2) and Rh(1), and of an intestinal bacterial metabolite, gINSenoside F(1, with high efficiency from a protopanaxatriol-type saponin mixture.
Abstract: During investigation of the hydrolysis of a protopanaxatriol-type saponin mixture by various glycoside hydrolases, crude preparations of beta-galactosidase from Aspergillus oryzae and lactase from Penicillium sp. were found to produce two minor saponins, ginsenoside Rg(2) [6-O-(alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl)-20(S)-protopanaxatriol] and ginsenoside Rh(1) (6-O-beta-D-glucopyranosyl-20(S)-protopanaxatriol), respectively, in high yields. Moreover, a naringinase preparation from Penicillium decumbens readily gave an intestinal bacterial metabolite, ginsenoside F(1) (20-O-beta-D-glucopyranosyl-20(S)-protopanaxatriol), as the main product, with a small amount of 20(S)-protopanaxatriol from a protopanaxatriol-type saponin mixture. Also, a hesperidinase from Penicillium sp. selectively hydrolyzed ginsenoside Re into ginsenoside Rg(1). This is the first report on the enzymatic preparation of minor saponins, ginsenosides Rg(2) and Rh(1), and of an intestinal bacterial metabolite, ginsenoside F(1), with high efficiency from a protopanaxatriol-type saponin mixture.
87 citations
TL;DR: The methanolic extract of the flowering stems of Vitex agnus-castus yielded three new iridoids that were tested for biological activities against various microorganisms and cancer cell lines.
74 citations
TL;DR: From the polar portion of the methanolic extract of the fruit of anise, four aromatic compound glucosides, an alkyl glucoside and a glucide were isolated together with 24 known compounds.
67 citations
TL;DR: A sulfated emodin glucoside was isolated from the roots of Rheum emodi in an investigation of the active constituents of this Nepalese medicinal plant, and its structure was determined by spectroscopic and chemical methods.
Abstract: A sulfated emodin glucoside, emodin 8-O-beta-D-glucopyranosyl-6-O-sulfate (1), was isolated from the roots of Rheum emodi in an investigation of the active constituents of this Nepalese medicinal plant, and its structure was determined by spectroscopic and chemical methods. Additionally, two rare auronols, carpusin (2) and maesopsin (3), besides other anthraquinones and phenolics, were isolated and identified. Compounds 2 and 3 showed significant antioxidant activity in the DPPH assay, while chrysophanol, physcion, and emodin and their 8-O-glucosides were found to be inactive.
TL;DR: The first report of aureusidin and 1-cinnamoyl-β-d -glucoside as blackcurrant constituents was made by.
TL;DR: The sum of all the flavone glycosides and soluble phenolic acids in the leaves decreased with increased rate of plant nutrients given in animal manure and with increased crop yield and the major phenylpropanoids showed the same general response to nutrient level.
Abstract: From the leaves of barley, Hordeum vulgare, one new flavone C-glucoside and three known flavone glucosides were isolated and characterized by (1)H and (13)C NMR and MALDI-TOF-MS. The novel flavone C-glucoside was isovitexin 7-O-beta-[6' "-O-(E)-p-coumaroyl]glucoside (6' "-coumaroylsaponarin), and the known compounds were isovitexin 7-O-beta-[6' "-O-(E)-feruloyl]glucoside, isoorientin 7-O-beta-[6' "-O-(E)-feruloyl]glucoside, and tricin 7-O-beta-glucoside. The sum of all the flavone glycosides and soluble phenolic acids in the leaves decreased with increased rate of plant nutrients given in animal manure and with increased crop yield. All of the major phenylpropanoids showed the same general response to nutrient level. The concentration of nitrogen in the leaves was not directly related to nutrient application or to contents of phenylpropanoids.
TL;DR: Four stilbene derivatives, gnemonols K and L, M, and gnemonoside K (glucoside of resveratrol trimer) together with eleven known stilbenoids and a lignan were isolated from the acetone, methanol and 70% meethanol soluble parts of the root of Gnetum gnemon (Gnetaceae).
TL;DR: From the water-soluble portion of the methanol extract of celery seed (fruit of Apium graveolens L.) five sesquiterpenoid glucosides and three phthalide glycosides were isolated together with six aromatic compound glucoside, two norcarotenoid glucOSides and a lignan glucOSide.
TL;DR: From seeds of Strychnos nux-vomica three iridoids were isolated together with two known iridoid glucosides, loganic acid and 7-O-acetylloganic acid, establishing the structures of the compounds.
TL;DR: Activity‐guided fractionation of the EtOAc and MeOH extract of the leaves of Syringa dilatata NAKAI furnished one free radical scavenger, the secoiridoid glucoside oleuropein together with ligstroside and an iridoid glucose, syringopicroside, which interacted with the stable free radical, 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH).
Abstract: Activity-guided fractionation of the EtOAc and MeOH extract of the leaves of Syringa dilatata NAKAI furnished one free radical scavenger, the secoiridoid glucoside oleuropein together with ligstroside and an iridoid glucoside, syringopicroside. Oleuropein interacted with the stable free radical, 1,1-diphenyl-2-picrylhydrazyl (DPPH), and showed an IC50 value of 40.4 µM. L-Ascorbic acid as a positive control showed an IC50 value of 50.3 µM. Copyright © 2003 John Wiley & Sons, Ltd.
TL;DR: The simultaneous separation and determination of the major anthraquinones, emodin, chrysophanol, and their glucosides, of Rumex japonicus HOUTT.
Abstract: The simultaneous separation and determination of the major anthraquinones, emodin, chrysophanol, and their glucosides, of Rumex japonicus HOUTT, and emodin and emodin glucoside, of Cassia tora L, Rhamnus purshiana DC, Polygonum multiflorum THUNB, and P cuspidatum SIEB et ZUCC, were achieved by cyclodextrin modified capillary zone electrophoresis The running electrolyte used in this method was 0005 M alpha-cyclodextrin in 003 M borate buffer (pH 105) containing 10% acetonitrile, with an applied voltage of 20 kV
Journal Article•
TL;DR: In this paper, the structures of the isolated compounds were elucidated by means of spectroscopic evidence, and they demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assay.
Abstract: From the aerial parts of Phlomis samia an iridoid glucoside, shanzhiside methylester (1), and three phenylethanoid glycosides, martynoside (2), 4''-O-acetylmartynoside (3) and samioside (4), were isolated. From the overground parts of P. monocephala two iridoid glucosides, lamiide (5) and ipolamiide (6), as well as three phenylethanoid glycosides, verbascoside (= acteoside) (7), forsythoside B (8), alyssonoside (9), and one lignan glucoside, syringaresinol 4'-O-b -D-glucopyranoside (10), were isolated. From the aerial parts of P. carica one phenylethanoid glycoside, verbascoside (= acteoside) (7) and three phenylpropanoid monomeric glucosides, syringin (11), dihydrosyringin (12) and coniferin (13), were isolated. The structures of the isolated compounds were elucidated by means of spectroscopic evidence. Phenylethanoid glycosides isolated from the title plants (2-4,7-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assay.
TL;DR: A new iridoid glycoside, gelsemiol 6'-trans-caffeoyl-1-glucoside, was isolated from Verbena littoralis and showed weak enhancement of nerve growth factor (NGF)-mediated neurite outgrowth from PC12D cells.
Abstract: A new iridoid glycoside, gelsemiol 6'-trans-caffeoyl-1-glucoside (1), was isolated from Verbena littoralis, together with four known phenylethanoid glycosides, acteoside (2), 2'-acetylacteoside (3), jionoside (4), and isoverbascoside (5). Their structures were elucidated by spectral data. Compound 1 showed weak enhancement of nerve growth factor (NGF)-mediated neurite outgrowth from PC12D cells.
TL;DR: The presence of the caffeoyl moiety is essential for both the antiperoxidative and radical scavenging activities, and the methylation of the quinic carboxyl group enhances the potency on xanthine oxidase inhibitory activity.
Abstract: The caffeoyl conjugates of prenylhydroquinone glucoside and of quinic acid, either in the carboxyl-free or carboxymethyl forms, isolated from Phagnalon rupestre (Asteraceae), showed inhibitory activity on lipid peroxidation induced by Fe 2+/ascorbate and by CCl4/NADPH in rat liver microsomes, with IC50 values ranging from 3 to 11 microM. After having demonstrated their effect on the xanthine oxidase-regulated superoxide production, the active compounds were tested for the direct inhibition of this enzyme. Methylated dicaffeoylquinic conjugates competitively inhibited the enzyme and the highest potency was obtained for the 4,5-diester, with an IC50 value of 3.6 microM, nearly ten times lower than that of the 3,5-analogue. In conclusion, the presence of the caffeoyl moiety is essential for both the antiperoxidative and radical scavenging activities, and the methylation of the quinic carboxyl group enhances the potency on xanthine oxidase inhibitory activity.
Journal Article•
TL;DR: In this paper, a neolignan glucoside dehyrodiconiferyl alcohol-4-O-b -D-glucopyranoside (1) was reported for the first time from a Phlomis species as well as for the family Lamiaceae.
Abstract: From the aerial parts of Phlomis integrifolia Hub.-Mor. (Lamiaceae) were isolated a neolignan glucoside, dehyrodiconiferyl alcohol-4-O-b -D-glucopyranoside (1), an ester flavone glycoside, chrysoeriol 7-O-(3''-O-trans-p-coumaroyl)-b -D-glucopyranoside (2), four phenylethanoid glycosides, forsythoside B (3), verbascoside (=acteoside) (4), leucosceptoside A (5) and martynoside (6) along with an iridoid glucoside, lamiide (7). The structure elucidation of the isolated compounds was carried out by spectroscopic (UV, IR, 1D- and 2D-NMR) methods. The isolation of neolignan glucoside dehyrodiconiferyl alcohol-4-O-b -D-glucopyranoside (1) is reported for the first time from a Phlomis species as well as for the family Lamiaceae.
Journal Article•
TL;DR: Ostra et al. as mentioned in this paper determined the derivatives of phenolic acids - ferulic and sinapic, as well as flavonoids - quercetin, luteolin and apigenin, were determined in pericarp of red pepper fruit cv. Bronowicka Ostra.
Abstract: The derivatives of phenolic acids - ferulic and sinapic, as well as flavonoids - quercetin, luteolin and apigenin, were determined in pericarp of red pepper fruit cv. Bronowicka Ostra. Nine compounds: trans-p-feruloyl-β-D-glucopyranoside, trams-p-ferulylalcohol-4-O-(6-(2-methyl-3-hydroxypropionyl) glucopyranoside, trans-p-sinapoyl-β-D-glucopyranoside, quercetin 3-O-α-L-rhamnopyranoside-7-O-β-D-glucopyranoside, quercetin 3-O-a-L-rhamnopyranoside, luteolin 6-C-β-D-glucopyranoside-8-C-a-L-arabinopyranoside, lutoeolin 7-O-[2-(β-D-apiofuranosyl)-β-D-glucopyranoside], luteolin-7-O-(2-apiofuranosyl--4-glucopyranosyl-6-malonyl) glucopyranoside, apigenin 6-C-β-D-glucopyranoside-8-C-a-L-arabinopyranoside were elucidated by 13 C and 1 H NMR, MS and HPLC methods. The quantification of these compounds in pepper fruit was determined by HPLC using the isolated compounds as the standards. The obtained results showed that the greatest amounts in pericarp of hot pepper fruit var. Bronowicka Ostra were the sinapic acid glucoside and then ferulic acid glucoside, luteolin apisylglucosidc and quercetin rhamnoside. The lowest level was found for apigenin 6-C-β-D-glucopyranoside-8-C-a-L-arabinopyranoside.
TL;DR: An alternative approach to the per-benzylated glycosylethenes has been studied and compared and a side reaction was explored to prepare beta-C-but-3-enyl glycosides and other beta- C-glycosyl derivatives by employing different Grignard reagents.
Abstract: Addition of vinylmagnesium bromide on the per-benzylated glucono-1,5-lactone gave, after reduction with Et3SiH/BF3·Et2O, a mixture of the desired β-C-vinyl glucoside 1 and the unexpected β-C-but-3-...
TL;DR: The acylated plant pigments synthesized by lipase-catalyzed transesterification with aromatic acids were compared in respect of their light-resistance and radical-scavenging ability and both were more stable against illumination with fluorescent light than their non-acylated glucosides.
Abstract: The acylated plant pigments synthesized by lipase-catalyzed transesterification with aromatic acids were compared in respect of their light-resistance and radical-scavenging ability. With both the flavonols and anthocyanins, their acylated derivatives were more stable against illumination with fluorescent light than their non-acylated glucosides. Their radical-scavenging ability partially decreased or was retained by acylation to the glucoside molecules.
Journal Article•
TL;DR: In this paper, a simple phenolic glucoside, 2,6-dimethoxy-4-hydroxyphenol-1-O-b -D-glucopyranoside (1), was extracted from P. carica.
Abstract: Phytochemical investigations on the aerial parts of Phlomis samia resulted in the isolation of a simple phenolic glucoside, 2,6-dimethoxy-4-hydroxyphenol-1-O-b -D-glucopyranoside (1); a megastigmane glucoside, phlomuroside (=3-hydroxy-5,6-epoxy-b -ionol-9-O-b -D-glucopyranoside) (2); and a nucleotide glycoside, uridine (3). From the aerial parts of P. carica, the same phenolic glucoside, 2,6-dimethoxy-4-hydroxyphenol-1-O-b -D-glucopyranoside (1); as well as an acetophenon glucoside, picein (4); and 2 monoterpenoid glucosides, - betulalbuside A (5) and 1-hydroxylinaloyl-6-O-b -D-glucopyranoside (6) - were isolated and identified. The structure elucidation of the isolates was based on spectroscopic evidence.
TL;DR: The experiments were performed on a group of both male and female F1 (CBA C57B1/6) mice and on male CBA mice weighing 20 – 22 g and found the cellular immunity was characterized by the delayed hypersensitivity (DHS) evaluated according to [7].
Abstract: 546 25 = –7°, and a purity above 98% (HPLC). The experiments were performed on a group of both male and female F1 (CBA C57B1/6) mice and on male CBA mice weighing 20 – 22 g. Animals in the uncured control group were treated with the immunodepressant drug azathioprine (Az) over five days in a daily dose of 50 mg/kg (p.o.). In the test group, monoglucoside I was introduced intraperitoneally as an aqueous solution in a dose of 5 g/kg against the background of azathioprine treatment. The reference drug was a liquid extract of Eleutherococcus senticosus (Rupr. Et Maxim.) Maxim (5 ml\"kg) known to possess immunomodulating properties [6]. Both the test compound and reference preparation were administered in a single daily dose over a period of 14 days. Animals in the intact control group received distilled water according to the same schedule. One day after the last treatment, the lymphoid organs (thymus and spleen) were extracted, weighed, and characterized by the percentage of total body weight. The state of the cellular immunity was characterized by the delayed hypersensitivity (DHS) evaluated according to [7]. The test mice were sensitized by intraperitoneal injections of an 0.1% suspension of goat erythrocytes (GE) in physiological solution. On the 4th day, a challenging dose of the antigen (50 l of a 50% GE suspension) was introduced by subplantar injection into the hind paw aponeurosis and the contralateral paw was injected with the same volume of pure physiological solution. The DHS response was determined 24 h later by measuring the difference in weights of the test (P0) and control (Pc) paws cut at the ankle joint. The response index (RI) was calculated by the formula
Journal Article•
TL;DR: Fractionation of ethyl acetate extract of Lavandula stoechas aerial parts revealed the presence of a novel acetylated glucoside together with apigenin 7-O-glucoside and luteolin 7- O-glUCoside, and the structures of these compounds were elucidated by spectroscopic analyses.
Abstract: Fractionation of ethyl acetate extract of Lavandula stoechas aerial parts revealed the presence of a novel acetylated glucoside (1) together with apigenin 7-O-glucoside (2) and luteolin 7-O-glucoside (3). The structures of these compounds were elucidated by spectroscopic analyses, notably UV, MS, and NMR.
TL;DR: In this article, three monoterpene glucosides (1-3), including one new compound (3), have been isolated from the methanol extract of Portulaca oleracea.
Abstract: Three monoterpene glucosides (1-3), including one new compound (3), have been isolated from the methanol extract of Portulaca oleracea. Structures of these compounds were determined to be (3S)-3-O-(β-D-glucopyranosyl)-3,7-dimethylocta-1,6-dien-3-ol (1), (3S)-3-O-(β-D-glucopyranosyl)-3,7-dimethylocta-1,5-dien-3,7-diol (2) and (3S)-3-O-(β-D-glucopyranosyl)-3,7-dimethyl-7-hydroperoxyocta-1,5-dien-3-ol (3), respectively, by a combination of spectral analyses. Their stereochemistries were established by measurement of NOE and vicinal proton-proton coupling constants as well as comparisons of spectral data with those of previously related compounds.
TL;DR: The difference in the activity between oleuropein, a secoiridoid glucoside, and the hydrolysed derivatives was not significant and the activity of the aglycone was significantly lower than that of the glucosides.
Abstract: Beta-sitosteryl-D-glucoside and oleuropein isolated from the olive tree (Olea europaea) and their hydrolysed derivatives were tested by a feeding stimulative activity bioassay using the olive weevil (Dyscerus perforatus). Although the steroidal glucoside showed potent feeding stimulative activity, the activity of the aglycone (beta-sitosterol) was significantly lower than that of the glucoside. On the other hand, the difference in the activity between oleuropein, a secoiridoid glucoside, and the hydrolysed derivatives was not significant.