Showing papers on "Glucoside published in 2010"
TL;DR: In this article, 13 phenolic constituents, luteolin (1), protocatechuic acid (2), caffeic acid(3), flavoyadorininin-B (4), 4,5-dicaffeoylquinic acid, rhoifolin (12), chlorogenic acid (13), and a novel phenolic glucoside benzoate, vanillic acid 4-O-β-d -(6-Obenzoylglucopyranoside) (6), were isolated from the flower buds of Lonic
183 citations
TL;DR: This study presented an efficient biotransformation for the conversion of rutin to Q3G which was newly shown to have more potent antiproliferative effect than quercetin and r Rutin.
Abstract: The flavonol quercetin in plants and foods occurs predominantly in the form of glycoside whose sugar moiety affects the bioavailability and the mechanism of its biological activities. The antiproliferative activities of quercetin derivatives such as quercetin aglycone, quercetin-3-β-d-glucoside (Q3G), and rutin were compared using six different cancer cell lines including colon, breast, hepatocellular, and lung cancer. The IC50 value of Q3G ranged between 15 and 25 μM in HT-29, HCT 116, MCF-7, HepG2, and A549 cells. In these five cell lines, Q3G showed the most potent growth inhibition, whereas rutin showed the least potency. Transformation of rutin to Q3G was conducted by controlling α-l-rhamnosidase and β-d-glucosidase activities from crude enzyme extract of Aspergillus niger. Carbon sources during culture and transformation conditions such as pH, temperature, and heat-stability were optimized. After 4 h biotransformation, 99% of rutin was transformed to Q3G and no quercetin was detected. This study pre...
87 citations
TL;DR: The glucoside was found in the juice extracts of grapes exposed to bushfire smoke, as well as grapes experimentally exposed to smoke, indicating glucosylation of guaiacol occurred following grapevine smoke exposure.
72 citations
TL;DR: Novel C-aryl glucoside SGLT2 inhibitors containing 1,3,4-thiadiazole moieties were designed and synthesized, and a selected compound 61, demonstrated reasonable blood glucose-lowering effects, indicating that the information obtained from the SAR studies might help to design more active SGLt2 inhibitors that are structurally related.
65 citations
TL;DR: A reversed phase high performance liquid chromatography (RP-HPLC) separation coupled with an electrospray ionisation mass spectrometry detection (ESI-MS) and the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay was used for the screening of multiple antioxidant compounds in Antidesma thwaitesianum Muell. as discussed by the authors.
65 citations
TL;DR: It is shown that different glycosyltransferases from M. x domestica could be responsible for phloridzin formation in planta and that Pyrus communis has the ability to glycoslyate phloretin, although no phlorein derivatives are present in this genus.
61 citations
TL;DR: This is the first report on isolation and identification of LNA, SG and LG from lime and their mechanism of inhibition of human pancreatic cancer cells and their results were further supported through fluorescent probed microscopic images.
61 citations
TL;DR: It was found that the number of glucosides in the structure may significantly influence their activities and cytotoxicity and the substitution of acyl group on glucoside may be important to keep the anti-HBV activities of these compounds.
52 citations
TL;DR: In this article, a double residue (N221S, P342L) mutant of the thermostable beta-glucosidase (TnBgl1A), isolated from the thermophile Thermotoga neapolitana and cloned and produced in E. coli, was used directly in yellow onion extracts, prepared by sub-critical water extraction, resulting in complete hydrolysis of the glucosylated flavonoids quercetin-3,4'-diglucoside, quercETin-4'-glucose, qu
49 citations
TL;DR: Fractionation of the water-soluble part of D. huoshanense by repeated chromatography culminated in the isolation of four new 6,8-di-C-glycosyl flavones (1-4), in addition to seven known compounds, comprising malic acid, dimethyl malate, N-phenylacetamide, isopentyl butyrate, salicylic acid, shikimic Acid, and isoschaftoside.
Abstract: Dendrobium huoshanense is a valued herbal plant used in traditional Chinese medicine. Fractionation of the water-soluble part of D. huoshanense by repeated chromatography culminated in the isolation of four new 6,8-di-C-glycosyl flavones (1-4), in addition to seven known compounds, comprising malic acid, dimethyl malate, N-phenylacetamide, isopentyl butyrate, salicylic acid, shikimic acid, and isoschaftoside. By detailed spectroscopic analysis, the structures of 1-4 were determined to have a core of apigenin bearing pentoside (arabinoside or xyloside) and rhamnosyl-hexoside (glucoside or galactoside) substituents.
48 citations
TL;DR: 4-hydroxycoumarin formation by biphenyl synthase (BIS) is reported and 3,5-dihydroxybiphenyl which is the precursor of the phytoalexins of the Maloideae is formed.
Abstract: Coumarin forms in melilotoside (trans-ortho-coumaric acid glucoside)-containing plant species upon cell damage. In moldy melilotoside-containing plant material, trans-ortho-coumaric acid is converted by fungi to 4-hydroxycoumarin, two molecules of which spontaneously combine with formaldehyde to give dicoumarol. Dicoumarol causes internal bleeding in livestock and is the forerunner of the warfarin group of medicinal anticoagulants. Here, we report 4-hydroxycoumarin formation by biphenyl synthase (BIS). Two new BIS cDNAs were isolated from elicitor-treated Sorbus aucuparia cell cultures. The encoded isoenzymes preferred ortho-hydroxybenzoyl (salicoyl)-CoA as a starter substrate and catalyzed a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin. When elicitor-treated S. aucuparia cell cultures were fed with the N-acetylcysteamine thioester of salicylic acid, 4-hydroxycoumarin accumulated in the culture medium. Incubation of the BIS isoenzymes with benzoyl-CoA and malonyl-CoA resulted in the formation of 3,5-dihydroxybiphenyl which is the precursor of the phytoalexins of the Maloideae.
TL;DR: Compound 22l exhibited reasonable urinary glucose excretion and glucosuria in normal SD rats, thereby demonstrating that this pyridazine series possesses both in vitro SGLT2 inhibition and in vivo efficacy, albeit to a lower degree.
TL;DR: Four new iridoids viz., plumeridoids A, B, and C and epiplumeridoid C were isolated from the stem bark of Plumeria rubra Linn and exhibited antifungal, antialgal, and/or antibacterial activities.
Abstract: Four new iridoids viz., plumeridoids A, B, and C and epiplumeridoid C were isolated from the stem bark of Plumeria rubra Linn. together with twenty-four known compounds viz., 1-( P-hydroxyphenyl)propan-1-one, isoplumericin, plumericin, dihydroplumericin, allamcin, fulvoplumerin, allamandin, plumieride, P- E-coumaric acid, 2,6-dimethoxy- P-benzoquinone, scopoletin, cycloart-25-en-3 beta,24-diol, 2,4,6-trimethoxyaniline, ajunolic acid, ursolic acid, oleanolic acid, beta-amyrin acetate, betulinic acid, lupeol and its acetate, 2,3-dihydroxypropyl octacosanoate, glucoside of beta-sitosterol, and a mixture of common sterols (stigmasterol and beta-sitosterol). Their structures were determined by means of spectroscopic data including HREIMS, 1H NMR, 13C NMR, 2D NMR (HMQC, HMBC, NOESY) and by comparison with published data. All but one of thirteen tested compounds exhibited antifungal, antialgal, and/or antibacterial activities.
TL;DR: Fifteen compounds were isolated from an EtOAc-soluble fraction of the flowers of Platycodon grandiflorum (balloonflower; Campanulaceae) by physical and spectroscopic methods, as well as by comparison of their data with literature values.
Abstract: In an ongoing project directed toward the discovery of novel treatments for diabetic complications from traditional herbal medicines, fifteen compounds, apigenin (1), apigenin-7-O-β-d-glucopyranoside (2), apigenin-7-O-(6″-O-acetyl)-β-d-glucopyranoside (3), luteolin (4), luteolin-7-O-β-d-glucopyranoside (5), luteolin-7-O-(6″-O-acetyl)-β-d-glucopyranoside (6), isorhamnetin-3-Oneohesperidoside (7), 4-O-caffeoylquinic acid (8), chlorogenic acid methyl ester (9), 4-O-β-d-glucopyranosylcaffeic acid (10), lobetyolin (11), cordifolioidyne C (12), isomultiflorenyl acetate (13), β-sitosterol glucoside (14), and α-spinosterol (15), were isolated from an EtOAc-soluble fraction of the flowers of Platycodon grandiflorum (balloonflower; Campanulaceae). The structures of the compounds were identified by physical and spectroscopic methods, as well as by comparison of their data with literature values. All the isolates were evaluated in vitro for inhibitory activity on the formation of advanced glycation end products and rat lens aldose reductase.
TL;DR: In this article, the authors examined whether growth under controlled artificial illumination could be used for cultivation of red perilla to enhance rosmarinic acid and luteolin content, and the results indicated that artificial illumination is effective for inducing the accumulation of polyphenols with functional food properties.
TL;DR: It is reported that OsTAGG1 is a specific beta-glucosidase hydrolyzing TAG, which releases the physiologically active TA, which was purified from rice by six purification steps with an approximately 4300-fold purification.
TL;DR: Among the compounds assayed, pyrimidine containing methylthio moiety 11 g demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date (IC(50)=10.7 nM).
01 Jan 2010
TL;DR: In this paper, the phenolic contents of carob pods from six regions in Morocco were measured by HPLC-ESI-MS and gas-chromatography mass spectrometry (GC-MS).
Abstract: The phenolic contents of ethanolic extracts of caro b pods from six regions in Morocco were measured in this work. The identification and quantification of individual target polyphenolic compounds were performed by high performance liquid-chromatography electrospray-ionisation mass spectrometry (HPLC-ESI-MS) and gas-chromatography mass spectrometry (GC-MS). A total of fifty two phenolic compounds were identified with a yield ranged from 9.15 mg/gm to 55.73 mg/gm. The predominant polyphenolic compounds in all analyzed carob pods extracts were gallic acid, gallate glucoside and gallic acid gluc oside. Gallic acid was the principal free phenolic acid in carob pods accounting for 17. 96 to 32.92% of the total phenolics present. Gallate glucoside was detected only in two regions (Essaouira and BeniMellal) with higher concentration (22.02% and 36.70%). Content of gallic acid glucoside ranged from 23.07 to 57.03% of the total phenol level in carob pods. Flavonol glycosides constituted 6.41 to 21.16% of t he polyphenols, and the major components were identified as the glycosides myrice tin rhamnoside and quercetin rhamnoside.
TL;DR: A new, stable hemi-aminal nor-tropane christened noeurostegine was synthesised in 22 steps from levoglucosan and tested for inhibitory activity against glycoside hydrolases.
Abstract: A new, stable hemi-aminal nor-tropane christened noeurostegine was synthesised in 22 steps from levoglucosan and tested for inhibitory activity against glycoside hydrolases. Sweet almond and Thermotoga maritimaβ-glucosidases, coffee bean α-galactosidase, and Asp. oryzaeβ-galactosidase were inhibited in the low micromolar region but significant tightening of binding to Ki 50 nM for almond β-glucosidase was found to occur after pre-incubation. Yeast α-glucosidase and E. coliβ-galactosidase were not inhibited at 1 mM.
TL;DR: Polyacetylenic glucosides (1-5) were isolated from the MeOH extract of Mediasia macrophylla, and their structures were established by spectroscopic analyses.
TL;DR: With increased electric field intensity or treatment time, the degradation of Cyd-3-glc and the formation of protocatechuic acid were enhanced; their kinetics were well fitted to a first-order reaction.
Abstract: Anthocyanins are polyphenol antioxidants that have been shown to prevent many chronic diseases. The compounds are not stable, so they tend to be decolorized or degraded during processing and storage. In this study, the spectral characteristics alteration and degradation products of cyanidin-3-glucoside (Cyd-3-glc) exposed to pulsed electric field (PEF) were investigated, and the reaction kinetics was discussed. The intensity of the UV−vis spectra decreased noticeably upon PEF treatment without modification of the spectral pattern. Protocatechuic acid and 2,4,6-trihydroxybenzoic acid were identified as degradation products of both PEF and thermally treated Cyd-3-glc, but cyanidin present in thermally treated Cyd-3-glc was absent in PEF-treated Cyd-3-glc, indicating that the first step of Cyd-3-glc degradation induced by PEF was not the hydrolysis of glycosidic bonds, which was different from that of thermal degradation. With increased electric field intensity or treatment time, the degradation of Cyd-3-glc...
TL;DR: The data shows that the botanical parts of C. densifolia Mart.
TL;DR: Three conjugates of the abscisic acid derivative (2Z,4E)-5-[(1S,3S,5R,8S)-3,8-dihydroxy-1,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid and phenolic glucosides (1
Abstract: Three conjugates of the abscisic acid derivative (2Z,4E)-5-[(1S,3S,5R,8S)-3,8-dihydroxy-1,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid and phenolic glucosides (1–3), and an eremophilane-type sesquiterpene glucoside (4), along with ten known compounds, were isolated from the roots of Lindera strychnifolia. The structures of all compounds were elucidated by means of spectroscopic analysis, and by application of the modified Mosher’s method for the methyl ester of the abscisic acid derivative and the octant rule for 4.
TL;DR: A new grayanol diterpenoid, grayanotoxin XXII, and a new phenolic glucoside, benzyl 2-hydroxy-4-O-[β-xylopyranosyl(1″ → 6′)-β-glucopyranoyl]-benzoate, were isolated from the flowers of Pieris formosa.
TL;DR: Saikachinoside A accelerated acetylcholinesterase activity by interpretation of the spectroscopic data and was confirmed by X-ray crystallographic analysis as discussed by the authors, and was determined as 7-β-dglucopyranosyl-3-[(Z)-4-hydroxy-3-methyl-2-butenyl]isoguanine.
TL;DR: From a 1-BuOH-soluble fraction of the MeOH extract of the leaves of Crotalaria zanzibarica collected in the Okinawa Islands, three new megastigmane glucosides, named crotalionosides A-C, two new pterocarpan glucoside and a chalcone C-glucoside were isolated.
Abstract: From a 1-BuOH-soluble fraction of the MeOH extract of the leaves of Crotalaria zanzibarica collected in the Okinawa Islands, three new megastigmane glucosides, named crotalionosides A—C, two new pterocarpan glucosides and a chalcone C-glucoside were isolated together with two known flavonoid glycosides and one known megastigmane glucoside. The structures of the new compounds were elucidated by a combination of spectroscopic analyses. The absolute configurations of allenic megastigmane glucosides were determined by application of the modified Mosher's method. Those of the allenic moieties were determined by interpretation of the circular dichroism (CD) spectra of the reduction products derived from citrosides A and B. The aglycones of pterocarpan glucosides were found to be melilotocarpan B and the absolute structure of the chalcone C-glucoside was determined by comparison of the CD spectral behavior with the reported values.
TL;DR: Okicamelliaside was 12,000 times more potent than the antihistaminic drug, ketotifen fumarate, in inhibiting the degranulation of RBL-2H3 cells.
Abstract: Guided by anti-degranulation assays, we isolated from leaves of Camellia japonica an ellagic acid glucoside named okicamelliaside. The structure was elucidated as 3,4-dioxoloellagic acid 4'-O-β-D-glucopyranoside by spectroscopic and chemical methods. Okicamelliaside was 12,000 times more potent than the antihistaminic drug, ketotifen fumarate, in inhibiting the degranulation of RBL-2H3 cells.
TL;DR: In this article, vanillin glucoside on reacting with OH radical gave transients with absorption peaks at 360 and 410 nm, respectively, and the species absorbing at 410 nm has been interpreted to be a hydroxyl radical adduct.
TL;DR: Two new acetophenone glucosides, 2,6-dihydroxy-4methoxyacetophenone 3-C-β-D-(6′-O-galloyl)glucoside (2), together with three known compounds, eugenin (3), 8C-glucosaylnoreugenin(4), and gallic acid (5) were isolated from the EtOAc soluble fraction of the MeOH extract of clove buds (Syzygium aromaticum) as discussed by the authors.
Abstract: Two new acetophenone glucosides, 2,6-dihydroxy-4-methoxyacetophenone 3-C-β-D-glucoside (1) and 2,6-dihydroxy-4-methoxyacetophenone 3-C-β-D-(6′-O-galloyl)glucoside (2), together with three known compounds, eugenin (3), 8-C-glucosylnoreugenin (4), and gallic acid (5) were isolated from the EtOAc soluble fraction of the MeOH extract of clove buds (Syzygium aromaticum). Of these, compound 2 showed significant prolyl endopeptidase inhibitory activity with IC50 value of 17.2±1.1 μM, suggesting it may have potential use against memory impairment and cognitive decline.
TL;DR: Rat experiments showed that the PAMAM dendrimer-arbutin conjugates significantly suppressed d-glucose-induced hyperglycemic effects and appears to be a good candidate as an oral anti-diabetic drug.