Showing papers on "Glucoside published in 2013"
TL;DR: In this article, the anthocyanin profile of red cabbage consisting of twenty derivatives of cyanidin glucosides was described by means of HPLC-DAD-MS/MS.
190 citations
TL;DR: In this article, the chemical composition and antioxidant potential of Vitis vinifera leaves from twenty Portuguese varieties (white and red) were evaluated for the first time, concerning their reducing total capacity, reducing power and DPPH radical scavenging capacity.
93 citations
TL;DR: The present review is an up-to-date summary of occurrence, botanical description, ethnopharmacology, bioactivity and toxicological studies related to P. macrocarpa.
Abstract: Phaleria macrocarpa, commonly known as Mahkota dewa is a medicinal plant that is indigenous to Indonesia and Malaysia. Extracts of P. macrocarpa have been used since years in traditional medicine that are evaluated scientifically as well. The extracts are reported for a number of valuable medicinal properties such as anti-cancer, anti-diabetic, anti-hyperlipidemic, anti-inflammatory, anti-bacterial, anti-fungal, anti-oxidant and vasorelaxant effect. The constituents isolated from different parts of P. macrocarpa include Phalerin, gallic acid, Icaricide C, magniferin, mahkoside A, dodecanoic acid, palmitic acid, des-acetylflavicordin-A, flavicordin-A, flavicordin-D, flavicordin-A glucoside, ethyl stearate, lignans, alkaloids andsaponins. The present review is an up-to-date summary of occurrence, botanical description, ethnopharmacology, bioactivity and toxicological studies related to P. macrocarpa.
75 citations
TL;DR: The gene encoding a β-glucosidase from the archaeon Thermofilum pendens was cloned and expressed in Escherichia coli and showed great potential in cellulose saccharification and the glucoside hydrolysis of natural compounds.
61 citations
TL;DR: The findings indicated that the citrus limonoids may have potential for the prevention of estrogen-responsive breast cancer (MCF-7) via caspase-7 dependent pathways.
Abstract: Lemons are a widely used citrus crop and have shown several potential health benefits. In the present study, the mechanism and effectiveness of the anti-cancer and anti-aromatase properties of limonoids were investigated for the first time. Defatted lemon (Citrus lemon L. Burm) seed powder was extracted with ethyl acetate (EtOAc) and methanol (MeOH) for 16 h each, successively. These extracts were fractionated using 1D (silica) and 2D (ion exchange and SP-70 columns) column chromatography to obtain nine limonoids. The compounds were identified by TLC, HPLC, and LC-MS techniques. A panel of 9 purified limonoids, including limonin, nomilin, obacunone, limonexic acid (LNA), isolimonexic acid (ILNA), nomilinic acid glucoside (NAG), deacetyl nomilinic acid glucoside (DNAG), limonin glucoside (LG) and obacunone glucoside (OG) as well as 4 modified compounds such as limonin methoxime (LM), limonin oxime (LO), defuran limonin (DL), and defuran nomilin (DN), were screened for their cytotoxicity on estrogen receptor (ER)-positive (MCF-7) or ER-negative (MDA-MB-231) human breast cancer cells. We further tested the mechanism of the anti-proliferative activity of limonoids using an in vitro aromatase enzyme assay and western blot with anti-caspase-7. Among the tested limonoids, 11 limonoids exhibited cytotoxicity on MCF-7 whereas 8 limonoids showed cytotoxicity against the MDA-MB-231 cell lines. Although most of the limonoids showed anti-aromatase activity, the inhibition of proliferation was not related to the anti-aromatase activity. On the other hand, the anti-proliferative activity was significantly correlated with caspase-7 activation by limonoids. Our findings indicated that the citrus limonoids may have potential for the prevention of estrogen-responsive breast cancer (MCF-7) via caspase-7 dependent pathways.
58 citations
TL;DR: It is proposed that the major compounds responsible for the cytotoxic activity of the olive-leaf extract in SKBR3 cells are oleuropein and the flavones luteolin and apigenin, since these compounds showed high uptake and their antitumor activity has been previously reported.
53 citations
TL;DR: In this paper, the effect of α and β-cyclodextrin on cyanidin-3-O -glucoside color was investigated by UV-visible absorption techniques.
44 citations
TL;DR: Nonanthocyanin secondary metabolites potentially contributing to the antiproliferative bioactivity of black raspberry fruits were extracted in ethyl acetate and isolated by semipreparative and analytical HPLC and analyzed by NMR, HPLC-ESI-MS, and ESI-MS/MS techniques.
Abstract: Nonanthocyanin secondary metabolites potentially contributing to the antiproliferative bioactivity of black raspberry (Rubus occidentalis L.) fruits were extracted in ethyl acetate and isolated by semipreparative and analytical HPLC and analyzed by NMR, HPLC-ESI-MS, and ESI-MS/MS techniques. Here we present complete and partial structures of a variety of the chemical entities such as quercetin 3-glucoside, quercetin 3-rutinoside, myricetin glucoside, dihydrokaempferol glucoside, benzoic acid β-d-glucopyranosyl ester, 3,4-dihydroxybenzoic acid, epicatechin, caffeic acid, p-coumaric acid, p-coumaryl glucoside, p-coumaryl sugar ester, ellagic acid, methyl ellagic acid acetylpentose, methyl ellagic acid valerylpentose, trans-piceid, phloretin glucoside (phloridzin), dihydrosinapic acid, salicylic acid β-d-glucopyranosyl ester, a salicylic acid derivative without attached sugar, p-alkylphenyl glucoside, and a citric acid derivative. To our knowledge, 15 of these compounds were not previously reported in black ...
39 citations
TL;DR: Intense phenolic synthesis was characteristic for the bordering zone between the healthy and infected plant tissue resulting in higher total phenolic content which might hinder the fungus to spread from the infected cells into the healthy tissue, suggesting a lesser role of apigenin glycosides in pepper plant defence against the Colletotrichum fungus.
38 citations
TL;DR: The isolation of a new phenylethanoid glucoside from the leaves of Jacaranda mimosifolia along with jacaranone is reported, followed by the comparative estimation of total antioxidant compounds, total polyphenols and total flavonoids from different solvent extracts of the leaves and flowers.
35 citations
TL;DR: The major glycoside product was identified as hydroquinone-1-O-alpha-D-glucopyranoside (alpha-arbutin) on the basis of mass spectrometric, nuclear magnetic resonance analysis and component analysis of its enzymatic hydrolysates.
TL;DR: These results strongly support the assignment of E490 as the acid/base catalyst in a beta-glucosidase from A. niger ASKU28, and provide crucial experimental support for the bioinformatic identification of the homologous residue in a range of related GH3 subfamily members.
TL;DR: Three new iridoid glucosides, 6″-O-trans-feruloylgenipin gentiobioside, 2'-O- trans-caffeoylgardoside, and one new bis-iridside, jasmigeniposide B, along with six known analogues, were isolated from the fruit of Gardenia jasminoides on the basis of spectroscopic analyses and chemical methods.
TL;DR: Secoiridoid glucosides, including two conjugates with a phenolic and two conjugal derivative of nicotinic acid derivative, together with seven known secoiridoids derivatives, were isolated from flower buds of Lonicera japonica by spectroscopic analyses.
TL;DR: A new compound, benzyl alcohol β-d -apiofuranosyl-(1→6)-β- d -(4-O-caffeoyl) glucopyranoside (1), was isolated from the seed of sunflower (Helianthus annuus), together with eight known phenolic compounds: caffeic acid (2), methyl caffeoate (3), chlorogenic acid (4), 4-O-, 4-Caffeoy lquinic acid(5), 3-O,caffeic acid derivatives showed a high antioxidant potency RE
TL;DR: The results indicate a good correlation between anthocyanins quantity and the antimalarial activity (R 2 ǫ = 0.79) and also to anticancer activity ( R 2 Â= 0.78) as mentioned in this paper.
TL;DR: Nine phenolic antioxidants were isolated from the genus Rosa for the first time, and compounds 5–9 exhibited strong scavenging activity in ABTS compared with the positive control l-ascorbic acid.
TL;DR: In this research, an Escherichia coli strain bearing the reconstructed uridine-diphosphate glucose (UDP-glucose) pathway cassette and a putative glycosyltransferase from Arabidopsis thaliana was developed as a host for the production of apigenin-7- O -β- d -glucoside (APG) and baicalein (BCG) from exogenously supplied flavone aglycones.
TL;DR: CCF containing these eight flavonoids could be a useful natural source in the development of a novel α-glucosidase inhibitory agent against diabetic complications.
Abstract: Inhibitors of carbohydrate-hydrolysing enzymes play an important role for the treatment of diabetes. One of the therapeutic methods for decreasing of postprandial hyperglycemia is to retard absorption of glucose by the inhibition of carbohydrate- hydrolysing enzymes, such as α-glucosidase, in the digestive organs. To investigate the therapeutic potential of compounds from natural sources, Callistephus chinensis flowers (CCF) were tested for inhibition of α-glucosidase, and acarboes was used as the positive control. The 70 % ethanol extract of CCF exhibited significant α-glucosidase inhibitory activities with IC50 value of 8.14 μg/ml. The stepwise polarity fractions of CCF were tested further for in vitro inhibition of α-glucosidase. The ethyl acetate (EtOAc) fraction exhibited the most significant inhibitory activity. Eight pure compounds, apigenin, apigenin-7-O-β-D- glucoside, kaempferol, hyperin, naringenin, quercetin, luteolin, and kaempferol-7-O-β-D- glucoside, were isolated (using enzyme assay-guide fractionation method) from the EtOAc fraction. Among these, quercetin was the most active one (IC50 values 2.04 μg/ml), and it appears that the inhibiting percentages are close to acarbose (IC50 values 2.24 μg/ml), the positive control, on α-glucosidase inhibition. HPLC/UV analysis indicated that the major components of CCF are kaempferol, hyperin and quercetin. The presented results revealed that CCF containing these eight flavonoids could be a useful natural source in the development of a novel α-glucosidase inhibitory agent against diabetic complications.
TL;DR: A new secoiridoid glucoside with a cyclobutane skeleton and three new acylated secoirised glucosides, 2'-(2,3-dihydroxybenzoyl)-gentiopicroside, along with two noriridoids and two known secoirids were isolated from Gentiana rigescens Franch.
TL;DR: In the in vitro assays, compound 1 and (−)-syringaresinol-4,4'-bis-O-β-D-glucopyranoside showed evident activity against glutamate-induced neurotoxicity in PC12 cells, and showed a selective cytotoxic activity against acute myeloid leukemia cell line MV4-11.
Abstract: A new 8,4¢-oxyneolignane glucoside 1 has been isolated from the stems of Dendrobium aurantiacum var. denneanum together with six known phenolic glucosides 2-7. The structure of the new compound, including its absolute configuration, was determined by spectroscopic and chemical methods as (–)-(7S,8R,7¢E)-4-hydroxy-3,3¢,5,5¢-tetramethoxy-8,4¢-oxyneolign-7¢-ene-7,9,9¢-triol 7,9¢-bis-O-β-D-glucopyranoside (1). In the in vitro assays, compound 1 and (-)-syringaresinol-4,4¢-bis-O-β-D-glucopyranoside (2) showed evident activity against glutamate-induced neurotoxicity in PC12 cells. Shashenoside I (4) showed a selective cytotoxic activity with the IC50 value of 4.17 μM against the acute myeloid leukemia cell line MV4-11, while it was inactive against 10 other human tumor cell lines.
TL;DR: In this paper, a new neolignan glucoside was isolated from the hairy roots of Cichorium intybus, and its structure was determined as (7S, 8R)-3′-demethyl-dehydrodiconiferyl alcohol-3′ -O-β-glucopyranoside based on a combination of 1D and 2D NMR techniques and CD data.
TL;DR: In this paper, three new glucosyloxybenzyl derivatives of (R)-2-bensylmalic acid, grammatophyllosides A, C, and D, and a new phenolic glucoside were isolated from the pseudobulbs of GPs, along with cronupapine, vandateroside II, gastodin, vanilloloside, orcinol glucosides, and isovitexin.
TL;DR: Data suggest that a GH1 β-glucosidase uses the same retaining catalytic mechanism to hydrolyze 1-O-acyl glucose ester and glucoside as well as other GH1 enzymes from different phylogenic clusters.
TL;DR: The results suggest that Q-3-G may be confirmed more effective and bioavailable food component than rutin and even quercetin because of its enhanced solubility and inhibitory properties.
Abstract: UNLABELLED Enzymatic bioconversion of rutin to quercetin-3-O-glucoside (Q-3-G) by Penicillium decumbens naringinase was increased with reaction pH increased approximately to pH 6.0. It resulted in greater than 92% production of Q-3-G due to the removal of the terminal rhamnose at the controlled pH 6.0. The enzymatic bioconversion of rutin to Q-3-G was repetitively performed, yielding 84% after 5 batches with little quercetin formation. Interestingly, the water solubility of Q-3-G was enhanced 69- and 328-fold over those of rutin and quercetin, which may make Q-3-G more bioavailable in food. Q-3-G was approximately 6- and 1.4-fold more potent than rutin as an inhibitor of human intestinal maltase and human DL-3-hydroxy-3-methylglutalyl coenzyme A reductase. Q-3-G was less potent (16- and 1.3-fold, respectively) than quercetin as an inhibitor of these enzymes. However, the results suggest that Q-3-G may be confirmed more effective and bioavailable food component than rutin and even quercetin because of its enhanced solubility and inhibitory properties. PRACTICAL APPLICATION Bioconverted intermediate, quercetin-3-O-glucoside (Q-3-G), was found and confirmed to be largely more soluble than rutin and quercetin in water solution, which might make it more bioavailable as food ingredient. In addition, Q-3-G inhibited mildly the intestinal maltase, which might act as antidiabetic substance by modulating the adsorption of glucose in the intestine.
TL;DR: The expression of Os TAGG2 is upregulated by wounding and by methyl jasmonate, suggesting that this isozyme is involved in responses to biotic stresses and wounding, but the physiological substrate of OsTAGG2 remains ambiguous.
Abstract: β-Glucosidases (EC 32121) split β-glucosidic linkages at the non-reducing end of glucosides and oligosaccharides to release β-D-glucose One of the important functions of plant β-glucosidase is deglucosylation of inactive glucosides of phytohormones to regulate levels of active hormones Tuberonic acid is a jasmonate-related compound that shows tuber-inducing activity in the potato We have identified two enzymes, OsTAGG1 and OsTAGG2, that have hydrolytic activity towards tuberonic acid β-D-glucoside in rice (Oryza sativa L) The expression of OsTAGG2 is upregulated by wounding and by methyl jasmonate, suggesting that this isozyme is involved in responses to biotic stresses and wounding, but the physiological substrate of OsTAGG2 remains ambiguous In this study, we produced recombinant OsTAGG2 in Pichia pastoris (rOsTAGG2P), and investigated its substrate specificity in detail From 1 L of culture medium, 21 mg of purified recombinant enzyme was obtained by ammonium sulfate precipitation and Ni-chelating column chromatography The specific activity of rOsTAGG2P (182 U/mg) was close to that of the native enzyme (171 U/mg), unlike recombinant OsTAGG2 produced in Escherichia coli, which had approximately 3-fold lower specific activity than the native enzyme The optimum pH and temperature for rOsTAGG2P were pH 34 and 60 °C After pH and heat treatments, the enzyme retained its original activity in a pH range of 34-98 and below 55 °C Native OsTAGG2 and rOsTAGG2P showed 45-47-fold higher activities towards salicylic acid β-D-glucoside, an inactive storage-form of salicylic acid, than towards tuberonic acid β-D-glucoside (TAG), although OsTAGG2 was originally isolated from rice based on TAG-hydrolytic activity
TL;DR: A new pyridine alkaloid-coupled iridoid glucoside, dipasperoside A, and 20 known compounds were isolated from a water extract of Dipsacus asper roots and evaluated for their inhibitory activity against nitric oxide production in a lipopolysaccharide-activated murine macrophage cell line, RAW264.7.
Abstract: A new pyridine alkaloid-coupled iridoid glucoside, dipasperoside A (1), and 20 known compounds (2–21) were isolated from a water extract of Dipsacus asper roots Compound 1 possessed a unique structural feature with a nicotinic acid nucleus coupled through C-5 with C-7 of a secoiridoid/iridoid glucoside dimer, and esterified with a C-7 hydroxyl group of an iridoid glucoside monomer All isolates were evaluated for their inhibitory activity against nitric oxide (NO) production in a lipopolysaccharide (LPS)-activated murine macrophage cell line, RAW2647
01 Apr 2013
TL;DR: The effect produced by iridoid glucoside on various parameters was comparable with that of glibenclamide, a well-known antihyperglycemic drug.
Abstract: The present study was designed to examine the antihyperlipidaemic potential of iridoid glucoside isolated from Vitex negundo leaves in STZ-induced diabetic rats. The levels of cholesterol (TC), triglycerides, lipoproteins, free fatty acids, phospholipids, fatty acid composition, proinflammatory cytokines, muscle glycogen content, and glucose transporter 4 (GLUT4) expression were estimated in control and diabetic rats. Oral administration of iridoid glucoside at a dose of 50 mg/kg body weight per day to STZ-induced diabetic rats for a period of 30 days resulted in a significant reduction in plasma and tissue (liver and kidney) cholesterol, triglycerides, free fatty acids, and phospholipids. In addition, the decreased plasma levels of high-density lipoprotein-cholesterol and increased plasma levels of low density lipoprotein- and very low density lipoprotein-cholesterol in diabetic rats were restored to near normal levels following treatment with iridoid glucoside. The fatty acid composition of the liver and kidney was analyzed by gas chromatography. The altered fatty acid composition in the liver and kidney of diabetic rats was also restored upon treatment with iridoid glucoside. Moreover, the elevated plasma levels of proinflammatory cytokines and decreased levels of muscle glycogen and GLUT4 expression in the skeletal muscle of diabetic rats were reinstated to their normal levels via enhanced secretion of insulin from the remnant β cells of pancreas by the administration of iridoid glucoside. The effect produced by iridoid glucoside on various parameters was comparable with that of glibenclamide, a well-known antihyperglycemic drug.
TL;DR: The structures of a new flavan-3-ol compounds isolated from Loropetalum chinense were elucidated on the basis of extensive spectroscopic analysis.