Showing papers on "Glucoside published in 2011"
TL;DR: Examination of the antioxidant and antihemolytic activities of crude, aqueous, and organic-aqueous extracts of maqui and murta together with their inhibiting effect on enzymes involved in the metabolism of carbohydrates provides the basis for further examination of the suitability of polyphenol-enriched extracts from maqua as nutritional or medicinal supplements with potential human health benefits.
Abstract: The objective of this work was to evaluate the antioxidant and antihemolytic activities of crude, aqueous, and organic-aqueous extracts of maqui (Aristotelia chilensis) and murta (Ugni molinae Turcz.), together with their inhibiting effect on enzymes involved in the metabolism of carbohydrates. Radical scavenging activity, inhibition of linoleic acid oxidation in a micellar system, antihemolytic activity, and inhibition of α-amylases and α-glucosidases were analyzed. Crude extracts of maqui leaves and fruits were found to be important sources of polyphenolic compounds, showing 69.0 ± 0.9 and 45.7 ± 1.1 mg GAE/g dm, respectively. Polyphenols from maqui leaves were active as antioxidants and antihemolytic compounds (p < 0.05), showing a noncompetitive inhibiting effect on α-glucosidase. Flavan-3-ol polymers and glycosylated flavonols, such as quercetin glucoside and kaempferol glucoside, were tentatively identified in extracts. This preliminary observation provides the basis for further examination of the s...
139 citations
TL;DR: In this article, the antioxidant properties of methanol extracts of cones and needles of the unexplored Juniperus sibirica Burgsdorf (Cupressaceae) species were examined using LC-MS/MS technique.
80 citations
TL;DR: Orostachys japonicus cultivated in the Republic of Korea was analyzed for flavonoid content via HPLC coupled to MS/MS in this article, and eight flavonoids and one alkaloid were characterised for the first time.
68 citations
TL;DR: In this article, the profiles of phenolic phytochemicals in the leaves of Korean purple perilla (cv. Bora, Perilla fructescens ) were investigated using reversed-phase C 18 column chromatography and HPLC with DAD-ESI/MS analysis.
61 citations
TL;DR: From the aerial parts of Helichrysum chasmolycicum P.H Davis, which is an endemic species in Turkey, the flavonoids apigenin, luteolin, kaempferol, 3,5-dihydroxy-6,7,8-trimethoxyflavone, 3.5-Dihydroxyl-6.7, 8,4′-tetramethoxyFLavone and quercetin 3-O-glucoside were isolated as discussed by the authors.
59 citations
TL;DR: Results show that the investigated species of Sideritis are systematically very closely related in terms of chemical constituents.
Abstract: Twenty-one samples of Sideritis species (S. scardica, S. raeseri, S. taurica, S. syriaca and S. perfoliata) from various locations on the Balkan Peninsula were evaluated for their chemical constituents. Chemical analyses were focused on secondary metabolites, particularly phenolic compounds, which have several roles in the plant physiological processes and have demonstrated significant health beneficial effects. The occurrence of hydroxycinnamic acids, phenylethanoid glycosides and flavonoids has been investigated in taxonomically related taxa of the genus Sideritis. A systematic method for phenolic compounds identification was developed using tandem mass spectrometry coupled to high performance liquid chromatography with diode array detection. Scanning for precursor ions of commonly found phenolics in Sideritis species using LC/MS11 with an ion trap instrument permitted the specific determination of hydroxycinnamic acid derivatives, and phenylethanoid and flavonoid glycosides. Further characterization of each phenolic compound was performed using MS/MS product-ion analysis and common-neutral-loss analysis. This on-line technique allowed identification of three hydroxycinnamic acid derivatives, eight phenylethanoid glycosides, and twenty-four flavonoid glycosides. All the taxa analysed produced very similar phenolic patterns characterized by the presence of 5-caffeoylquinic acid, lavandulifolioside, verbascoside, hypolaetin 7-O-[6'''-O-acetyl]-allosyl(1-->2)glucoside, apigenin 7-(4"-p-coumaroylglucoside), 4'-O-methylisoscutellarein 7-O-[6'''-O-acetyl]-allosyl(1-->2)glucoside, and minor amounts of isoverbascoside, apigenin 7-O-allosyl(1-->2)glucoside, isoscutellarein 7-O-allosyl-(1-->2)-[6"-O-acetyl]-glucoside, hypolaetin 7-O-allosyl-(1-->2)-[6"-O-acetyl]-glucoside and 4'-O-methylhypolaetin 7-O-[6'''-O-acetyl]-allosyl-(1-->2)-[6"-O-acetyl]-glucoside. These results show that the investigated species are systematically very closely related. Phenylethanoid glycosides and flavonoid acetylglycosides are dominant and constitute 90% of the total phenolic compounds compared with hydroxycinnamic acid and flavonoid 7-O-glycosides. Principal component analysis (PCA) was performed for the nature and content of the different compounds to be correlated to the particular Sideritis species and also to the locations.
54 citations
TL;DR: Findings demonstrate that the methanol extract from L. viridis is a potential source of natural antioxidants and cholinesterase inhibitors and prevents Fe(2+)-induced lipid peroxidation.
50 citations
TL;DR: Cell cultures established from plants represent an attractive alternative to whole plants for effective production of bioactive secondary metabolites and two new compounds were identified: 3-O-glucosylresveratrol, a stilbene derivative, abundant in cell suspension culture, and a hydroxyphenol, 4-(3,5-dihydroxyyphenyl)-phenol, abundantly in callus culture.
Abstract: Cell cultures established from plants represent an attractive alternative to whole plants for effective production of bioactive secondary metabolites. Cell culture from Vitis vinifera L. cv. Gamay Freaux accumulated high amounts of hydroxycinnamic acid derivatives and anthocyanins. Two new compounds were identified: 3-O-glucosylresveratrol, a stilbene derivative, abundant in cell suspension culture, and a hydroxyphenol, 4-(3,5-dihydroxyphenyl)-phenol, abundant in callus culture. The major anthocyanin monoglucosides present in cell suspension culture were cyanidin 3-O-glucoside and peonidin 3-O-glucoside, and the major cinnamoyl derivatives were cyanidin 3-O-p-coumaryl glucoside and peonidin 3-O-p-coumaryl glucoside. Three minor anthocyanin compounds were found in V. vinifera cell culture: delphinidin 3-O-glucoside, petunidin 3-O-glucoside, and delphinidin 3-O-p-coumaryl glucoside. Anthocyanin levels of cell suspension cultures increased significantly—about eight fold—after 4-day cultivation in new medium. Salicylic acid at a concentration of 50 μM did not enhance anthocyanin accumulation in cell suspension culture, and similar levels of jasmonic acid significantly reduced the anthocyanin content.
45 citations
TL;DR: The developed method was successfully applied to complex citrus samples for the separation and identification of aglycones and glucosides of limonoids from citrus and is the first report on the identification of citrus limonoid using CID technique.
Abstract: Limonoids are considered as potential cancer chemopreventive agents and are widely distributed in the Citrus genus as aglycones and glucosides. In the present study, reversed-phase HPLC coupled with CID mass spectra was developed for the simultaneous separation and identification of aglycones and glucosides of limonoids from citrus. Five aglycones such as limonin, deacetyl nomilin, ichangin, isolimonoic acid and nomilin were identified by positive ion CID MS/MS, whereas five glucosides, viz. limonin glucoside, isoobacunoic acid glucoside, obacunone glucoside, deacetyl nomilinic acid glucoside and nomilinic acid glucoside were analyzed by negative ion CID mass spectra. The developed method was successfully applied to complex citrus samples for the separation and identification of aglycones and glucosides. Citrus seeds were extracted with methanol and partially purified and analyzed by LC-CID mass spectra. The separation was achieved by C-18 column; eight limonoids were identified by comparing the retention times and mass spectral fragmentation. To the best of our knowledge, this is the first report on the identification of citrus limonoids using CID technique.
40 citations
TL;DR: It is speculated that rutin may have been produced initially in plants as a possible defense mechanism for protection and survival under oxidative assaults and where both flavonoids are found to co-exist in nature, there is a possible synergy in their antioxidant actions.
39 citations
TL;DR: The structure-activity relationship indicated that the presence of 2-(3,4-dihydroxyphenyl)-ethoxy group is important for exhibiting the activity of superoxide anion scavenging activity in bark of Syringareticulata.
TL;DR: Novel C-aryl glucoside S GLT2 inhibitors containing the thiazole motif were designed and synthesized for biological evaluation and demonstrated the best in vitro inhibitory activity against SGLT2 to date.
Abstract: Novel C-aryl glucoside SGLT2 inhibitors containing the thiazole motif were designed and synthesized for biological evaluation Among the compounds assayed, thiazole containing furanyl moiety 14v and thiophenyl moiety 14y demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date (IC50 = 0720 nM for 14v and IC50 = 0772 nM for 14y) Both of these compounds have been further evaluated on a urinary glucose excretion test and the urine volumes excreted
TL;DR: In this paper, a new secoiridoid, oleuropein-3″-methyl ether (OLEA europaea L) was identified by combining HPLC with fast on-line post-column radical scavenging activity evaluation.
TL;DR: Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM and derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol.
TL;DR: A kinetic study established that both mono- and bis-triazole-linked glycosyl acids act as typical competitive inhibitors whereas the bis-Triazolyl ester that also exhibited inhibitory activity on PTP1B displayed a mixed-type inhibition pattern.
Abstract: There has been increasing interest in the development of protein tyrosine phosphatase 1B (PTP1B) inhibitors for the treatment of type 2 diabetes, obesity and breast cancer We report here the identification of a series of mono- and bis-phenylalaninyl and tyrosinyl glucoside derivatives as novel PTP1B inhibitors The designed compounds bearing one or two phenylalanine or tyrosine derivatives on the 6-, 2,3-, 2,6-, 3,4- and 4,6-positions of the glucosyl scaffolds were efficiently constructed via the microwave-assisted Cu(I)-catalyzed azide–alkyne cycloaddition in moderate-to-excellent yields Successive biological assays identified these compounds as novel PTP1B inhibitors, with the 4,6-disubstituted tyrosinyl glucoside being the most potent A kinetic study established that both mono- and bis-triazole-linked glycosyl acids act as typical competitive inhibitors whereas the bis-triazolyl ester that also exhibited inhibitory activity on PTP1B displayed a mixed-type inhibition pattern Furthermore, docking simulation plausibly proposed the diverse binding modes of these compounds with the enzymatic target
TL;DR: The formation of acyl glycoside metabolites of R- and S-ibuprofen (Ibu) by human liver microsomes supplied with the cofactor UDP-glucose is discovered and this gene fyu1 is suggested to be named for fission yeast UGPase1.
Abstract: UDP-glycosyltransferases (UGTs) are an important group of enzymes that participate in phase II metabolism of xenobiotics and use the cofactor UDP-glucuronic acid for the production of glucuronides. When acting on molecules bearing a carboxylic acid they can form acyl glucuronides, a group of metabolites that has gained significant interest in recent years because of concerns about their potential role in drug toxicity. In contrast, reports about the production of drug acyl glucosides (which might also display high reactivity) have been scarce. In this study, we discovered the formation of acyl glycoside metabolites of R- and S-ibuprofen (Ibu) by human liver microsomes supplied with the cofactor UDP-glucose. Subsequently, human UGT2B7*1 and UGT2B7*2 recombinantly expressed in fission yeast Schizosaccharomyces pombe could be shown to catalyze these reactions. Moreover, we could enhance the glucoside production rate in fission yeast by overexpressing the fission yeast gene SPCC1322.04, a potential UDP-glucose pyrophosphorylase (UGPase), but not by overexpression of SPCC794.10, and therefore suggest to name this gene fyu1 for fission yeast UGPase1. It was interesting to note that pronounced differences between the two polymorphic UGT2B7 variants were observed with respect to acyl glucoside production. Finally, using the metabolic precursor [13C6]glucose, we demonstrated the production of stable isotope-labeled reference standards of Ibu acyl glucoside and Ibu acyl glucuronide by whole-cell biotransformation in fission yeast.
TL;DR: Glucopiericidin C: a cytotoxic piericid in glucoside antibiotic produced by a marine Streptomyces isolate that acts as a “spatially aggregating agent” to kill Gram-negative protozoa.
Abstract: Glucopiericidin C: a cytotoxic piericidin glucoside antibiotic produced by a marine Streptomyces isolate *
TL;DR: In LM of the investigated flaxseed, one molecule of caffeic acid corresponded with five molecules of p-coumaric acid and two molecules of ferulic acid, which might be very beneficial due to its high antioxidant activity.
Abstract: Phenolic compounds were extracted from defatted flaxseeds using ethanol-dioxane (1:1, v/v). The crude extract obtained was purified using Amberlite XAD-16 column chromatography with water and methanol as mobile phases. RP-HPLC and SE-HPLC showed a lignan macromolecule (LM) as a dominant phenolic compound in the purified extract. After the alkaline hydrolysis of LM caffeic acid glucoside (CaAG) was isolated using a semi-preparative HPLC and its structure was confirmed by LC-ESI-MS. In LM of the investigated flaxseed, one molecule of caffeic acid corresponded with five molecules of p-coumaric acid and two molecules of ferulic acid. The presence of caffeic acid in the lignan molecule might be very beneficial due to its high antioxidant activity.
Patent•
30 Jun 2011
TL;DR: In this article, C-aryl glucoside derivatives, preparation processes and pharmaceutical uses thereof are disclosed, with each substituent defined in the application, pharmaceutically acceptable salts or stereoisomers thereof, their preparation methods, and pharmaceutical compositions containing the derivatives as well as their uses as therapeutic agents, particularly as sodium-dependent glucose cotransporter (SGLT)-1 inhibitors, are disclosed.
Abstract: C-aryl glucoside derivatives, preparation processes and pharmaceutical uses thereof are disclosed. In particular, C-aryl glucoside derivatives represented by formula (I), with each substituent defined in the application, pharmaceutically acceptable salts or stereoisomers thereof, their preparation methods, and pharmaceutical compositions containing the derivatives as well as their uses as therapeutic agents, particularly as sodium-dependent glucose cotransporter (SGLT)-1 inhibitors, are disclosed.
TL;DR: Among the compounds tested, ethylphenyl at the distal ring 71p showed the best in vitro inhibitory activity in this series to date (IC(50)=4.47 nM) against SGLT2.
TL;DR: Although the antioxidant activity was 1.5-fold lower, the advantage of the enhanced solubility and stability makes the EC3A glucoside more beneficial as food ingredient than its parent EC.
Abstract: Enzymatic synthesis of (−)-epicatechin (EC) glucosides was performed through the transglucosylation reaction catalyzed by the cyclodextrin glycosyltransferase (CGTase) from Paenibacillus sp. RB01. The enzyme showed the same product specificity for the three donor substrates, starch, β-cyclodextrin and maltoheptaose (G7). Using β-cyclodextrin as the glucosyl donor, several EC glucoside products were obtained at an overall minimal yield of 18.1%. The structures of the four main products were elucidated by MS and NMR techniques as (−)-EC-3′-O-α-d-glucopyranoside (EC3A), (−)-EC-3′-O-α-d-diglucopyranoside (EC3B), (−)-EC-3′-O-α-d-triglucopyranoside (EC3C) and (−)-EC-4′-O-α-d-glucopyranoside (EC4A). Of these, EC3A was the major product while EC4A, unique for this CGTase, was formed in the lowest amount. The water solubility and stability against UV irradiation of EC3A were significantly higher than that of EC. Although the antioxidant activity was 1.5-fold lower, the advantage of the enhanced solubility and stability makes the EC3A glucoside more beneficial as food ingredient than its parent EC.
TL;DR: A novel 20-norpimarane glucoside, xylopimarane, together with the known sphaeropsidin C and clonostachydiol, was isolated from the fungus Xylaria sp.
Abstract: A novel 20-norpimarane glucoside, xylopimarane (1), together with the known sphaeropsidin C (2) and clonostachydiol (3), was isolated from the fungus Xylaria sp. BCC 4297. Compound 1 exhibited cytotoxicity to cancer cell lines KB, MCF-7, and NCI-H187 with respective IC50 values of 1.0, 13, and 65 μM.
TL;DR: 3,12-Dihydroxy-cis-3,4-methylenedodecanoic acid 3-O-β-d-glucopyranoside, trivially named litchioside C (1), the first cyclopropyl-containing fatty acid glycoside, was isolated along with three previously uncharacterized galactosylacylglycerols from the seeds of Litchi chinensis.
TL;DR: Six triterpenes and a triterpene glucoside were isolated from the MeOH extract of the leaves of Dysoxylum cumingianum and compounds 1, 2 and 5 demonstrated significantly enhanced cytotoxicity against KB-C2 cells in the presence of 2.5 μM colchicine, suggesting that these triter penes might show some MDR-reversing effects.
Patent•
11 Jul 2011
TL;DR: C-aryl glucosides which are inhibitors of sodium dependent glucose transporters found in the intestine and kidney (SGLT2) are shown as formula I, a pharmaceutical composition and pharmaceutical combination as mentioned in this paper.
Abstract: C-aryl glucosides which are inhibitors of sodium dependent glucose transporters found in the intestine and kidney (SGLT2), shown as formula I, a pharmaceutical composition and pharmaceutical combination
Journal Article•
TL;DR: Six new steroidal lactones and a homomonoterpenic glucoside along with beta-sitosterol-3-beta-D-glucopyranoside are isolated in Malvaceae.
Abstract: Phytochemical investigation of the ethanolic extract of defatted fruits of Malva sylvestris Linn. (Malvaceae) led to the isolation of six new steroidal lactones and a homomonoterpenic glucoside along with beta-sitosterol-3-beta-D-glucopyranoside. The structures of new phytoconstituents have been elucidated as cholest-5-en-3a-ol-18(21)-olide (sylvestrosterol A), cholest-9(11)-en-3alpha-ol-18(21)-olide (sylvestrosterol B), cholest-4,6,22-trien-3alpha-ol-18(21)-olide (sylvestrosterol C), 2-methyl-6-methylene-n-decan-2-olyl- 3beta-D-glucopyranoside (malvanoyl glucoside), cholest-7-en-18(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin A), cholest-9(11)-en-18(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin B) and cholest-5-en-8(21)-olide-3alpha-olyl-3beta-D-glucopyranoside (sylvestrogenin C).The structures of all these phytoconstituents have been established on the basis of spectral data analysis and chemical reactions.
TL;DR: In this paper, ten flavonoids were isolated for the first time from the aerial parts of Sisymbrium irio L. grown in Saudia Arabia, using chromatographic methods.
TL;DR: Phytochemical investigation of Helleborus niger L. (Ranunculaceae) leaf methanol extract allowed to isolate a phenolic glucoside derivative and two flavonoid glycosides characterized as phenyllactic acid and kaempferol.
TL;DR: From aerial parts of Dianthus japonicus, six new and seven known oleanane-type triterpene saponins were isolated and elucidated by means of high resolution mass spectrometry, and extensive inspection of one- and two-dimensional NMR spectroscopic data.
Abstract: From aerial parts of Dianthus japonicus, six new and seven known oleanane-type triterpene saponins were isolated The structures of the new saponins, named dianthosaponins A-F, were elucidated by means of high resolution mass spectrometry, and extensive inspection of one- and two-dimensional NMR spectroscopic data A new C-glycosyl flavone, a glycosidic derivative of anthranilic acid amide and a maltol glucoside were also isolated
TL;DR: Novel C-aryl glucoside S GLT2 inhibitors containing cyclic diarylpolynoid motif were designed and synthesized for biological evaluation and demonstrated moderate in vitro inhibitory activity against SGLT2.