Showing papers on "Glucoside published in 2009"
TL;DR: Results showed that quercetin 3-O-glucoside exhibits high antioxidant effect, it has low cytotoxicity and no antibacterial effects, and it is assumed that Q3G does not play a defense role in plants and it may act as an allelopatic agent.
Abstract: Cytotoxic, phytotoxic, antimicrobial and antioxidant effects of quercetin 3- O -glucoside (Q3G) iso- lated by HPLC from aerial parts of Prangos ferulaceae was studied by MTT assay, lettuce germination assay, disk diffusion and DPPH method. Our results showed that Q3G exhibits high antioxidant effect with RC 50 of 22 µ g/mL, it has low cytotoxicity and no antibacterial effects. Q3G exhibits high phytotoxic effect with IC 50 value of 282.7 µ g/ml, as well. It is assumed that Q3G does not play a defense role in plants and it may act as an allelopatic agent.
108 citations
TL;DR: Interestingly, resveratrol and piceatannol inhibited both ATPase and ATP synthesis whereas quercetin,quercetrin or quercETin-3-beta-d glucoside inhibited only ATPase activity and not ATP synthesis.
98 citations
TL;DR: Deoxyarbutin exerts potent tyrosinase inhibition, lessened cytotoxicity, and certain antioxidation potential, may serve as an effective and safe alternative to hydroquinone for use in skin whitening.
98 citations
TL;DR: Two new compounds from the leaves of Aquilaria sinensis showed inhibition activity against polymorphonuclear neutrophils (PMNs) respiratory burst stimulated by PMA and were identified as novel benzophenone glucoside and new flavonoid.
Abstract: From the leaves of Aquilaria sinensis (LOUR) GILG, a novel benzophenone glucoside, designated as aquilarinoside A (1), and a new flavonoid, as 7-beta-D-glucoside of 5-O-methylapigenin (2), along with eight known compounds (3-10) were isolated The structures of 1 and 2 were fully characterized by spectroscopic methods (1D, 2D NMR and MS) and the relative stereochemistry was assigned based on nuclear Overhauser effect spectroscopy (NOESY) correlations and analyses of coupling constants The new compounds showed inhibition activity against polymorphonuclear neutrophils (PMNs) respiratory burst stimulated by PMA
75 citations
TL;DR: In this paper, a hydroquinone glucoside (HG) was synthesized as a potential skin whitening agent using Leuconostoc mesenteroides (B-1299CB BF563) dextransucrase with Hydroquinone (HQ) as an acceptor and sucrose as a donor.
47 citations
TL;DR: From the bark of Vitex pinnata, one new iridoid glucoside, pinnatoside and three known flavonoids, visciosides, apigenin, and luteolin were isolated and Structures of these compounds were determined from NMR spectroscopic studies.
Abstract: From the bark of Vitex pinnata, one new iridoid glucoside, pinnatoside (1) and three known flavonoids, viscioside (2), apigenin (3), and luteolin (4), were isolated. Structures of these compounds were determined from NMR spectroscopic studies. Compound 1 exhibited modest antifungal activity against Candida albicans.
43 citations
TL;DR: Quantification of compounds showed that free vanillin can reach 24% of the total vanillin content after 8 months of development in the vanilla green pods.
Abstract: The metabolomic analysis of developing Vanilla planifolia green pods (between 3 and 8 months after pollination) was carried out by nuclear magnetic resonance (NMR) spectroscopy and multivariate data analysis. Multivariate data analysis of the (1)H NMR spectra, such as principal component analysis (PCA) and partial least-squares-discriminant analysis (PLS-DA), showed a trend of separation of those samples based on the metabolites present in the methanol/water (1:1) extract. Older pods had a higher content of glucovanillin, vanillin, p-hydroxybenzaldehyde glucoside, p-hydroxybenzaldehyde, and sucrose, while younger pods had more bis[4-(beta-D-glucopyranosyloxy)-benzyl]-2-isopropyltartrate (glucoside A), bis[4-(beta-D-glucopyranosyloxy)-benzyl]-2-(2-butyl)tartrate (glucoside B), glucose, malic acid, and homocitric acid. A liquid chromatography-mass spectrometry (LC-MS) analysis targeted at phenolic compound content was also performed on the developing pods and confirmed the NMR results. Ratios of aglycones/glucosides were estimated and thus allowed for detection of more minor metabolites in the green vanilla pods. Quantification of compounds based on both LC-MS and NMR analyses showed that free vanillin can reach 24% of the total vanillin content after 8 months of development in the vanilla green pods.
40 citations
TL;DR: Structural analyses using 13 C and 1 H NMR proved that the transglycosylated product was 4-hydroxyphenyl β-maltoside (Ab-α-glucoside), in which a glucose molecule was linked to arbutin via an α-(1 → 4)-glycosidic linkage.
Abstract: Arbutin (Ab, 4-hydroxyphenyl β-glucopyranoside) is a glycosylated hydroquinone known to prevent the formation of melanin by inhibiting tyrosinase. An arbutin-α-glucoside was synthesized by the transglycosylation reaction of amylosucrase (AS) of Deinococcus geothermalis (DGAS) using arbutin and sucrose as an acceptor and a donor, respectively. The maximum yield of the arbutin transglycosylation product was determined to be over 98% with a 1:0.5 molar ratio of donor and acceptor molecules (sucrose and arbutin), in 50 mM sodium citrate buffer pH 7 at 35 °C. TLC and HPLC analyses revealed that only one transglycosylation product was observed, supporting the result that the transglycosylation reaction of DGAS was very specific. The arbutin transglycosylation product was isolated by preparative recycling HPLC. The structural analyses using 13 C and 1 H NMR proved that the transglycosylated product was 4-hydroxyphenyl β-maltoside (Ab-α-glucoside), in which a glucose molecule was linked to arbutin via an α-(1 → 4)-glycosidic linkage.
40 citations
Journal Article•
TL;DR: In this article, the authors used spectrophotometric methods to determine the polyphenolic composition and antioxidative properties of leaves extracted from Vitis vinifera during the growing season (May leaves) and after harvest (September leaves).
Abstract: In the present investigation, leaf ethanolic extracts of Vitis vinifera were assayed for their polyphenolic composition and antioxidative properties. The leaves were collected during lush vegetation period (May leaves) and after the harvest (September leaves). Air dried plant material was homogenized and the polyphenolic constituents were extracted using conventional solvent extraction procedure. Total phenolics, flavonoids, non-flavonoids, catechins and flavanols were determined using spectrophotometric methods. Both extracts were very rich in phenolic compounds. The concentration of total phenols in September leaves extract was about 30 % higher compared to May leaves extract, due to the increase of flavonoid (catechin) fraction. Nonflavanoid compound content was almost equal in both extracts. The amount of flavanols, determined with p-dimethylaminocinnamaldehyde method, was taken as indicator of flavan-3-ol monomers, while high catechin content determined by vanillin method, indicated the presence of polymeric fraction. The total catechin content in September leaves extract was more than 3 folds higher in comparison to May leaves extract. Principal phenolic compounds were separated by high pressure liquid chromatography on reverse phase. Antioxidant properties, determined as: 2, 2-diphenyl-2-picrylhydrazyl radical and 2, 2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate radical cation scavenging ability, ferric reducing/antioxidant power, Fe2+ chelating activity, and using β-carotene bleaching assay, were total phenol concentration dependent. September leaves extract had better free radical scavenging capacity, higher reducing power, and was more efficient in protecting the oxidation of emulsified linoleic acid, in comparison with May leaves extract which showed better chelating ability. The presence of active phenolic compounds: phenolic acids (3-hydroxybenzoic acid, caffeic acid, gallic acid, vanillin acid), flavonoids ((+)-catechin, (-)-epicatechin, apigenin, myricetin, quercetin, quercetin-4'-glucoside, rutin), and stilbenes (trans-resveratrol and resveratrol derivatives) was confirmed in both extracts. According to the results achieved, vine leaf extracts can be considered rich natural source of polyphenols with significant antioxidant properties.
38 citations
TL;DR: In this article, a recombinant sucrose phosphorylase (SPase) from Bifidobacterium longum was used to transglucosylate polyphenolic compounds.
28 citations
TL;DR: The antioxidant activity of the aqueous ethanolic extract of doum leaves, Hyphaene thebaica L.(Palmae) was studied in this article, where the extract can inhibit reactive oxygen species attack on salicylic acid in a dose dependant manner using xanthine/hypoxanthine oxidase assay.
Abstract: The antioxidant activity of the aqueous ethanolic extract of doum leaves, Hyphaene thebaica L. (Palmae) was studied. Data obtained showed that the extract can inhibit reactive oxygen species attack on salicylic acid (IC50 = 1602 µg/ml) in a dose dependant manner using xanthine/hypoxanthine oxidase assay. Four major flavonoidal compounds were identified by LC/SEI as; Quercetin glucoside,Kaempferol rhamnoglucoside and Dimethyoxyquercetin rhamnoglucoside. While, further in-depth phytochemical investigation of this extract lead to the isolation and identification of fourteen compounds; their structures were elucidated based upon the interpretation of their spectral data (UV, 1H, 13C NMR and ESI/MS) as; 8-C-β-D-glucopyranosyl-5, 7, 4`-trihydroxyflavone (vitexin) 1, 6-C-β-D-glucopyranosyl-5, 7, 4`-trihydroxyflavone (iso-vitexin) 2, quercetin 3-O-β-4C1-D-glucopyranoside 3, gallic acid 4, quercetin 7-O-β-4C1-D-glucoside 5, luteolin 7-O-β-4C1-D-glucoside6, tricin 5 O-β-4C1-D-glucoside 7, 7, 3` dimethoxy quercetin 3-O-[6''-O-α-L-rhamnopyranosyl]-β-D-gluco-pyranoside (Rhamnazin 3-O-rutinoside) 8kaempferol-3-O-[6''-O-α-L-rhamnopyranosyl]-β-D-glucopyranoside (nicotiflorin) 9, apigenin 10, luteolin 11, tricin 12, quercetin 13 and kaempferol 14.
Key words: Doum leaves, Hyphaene thebaica (Palmae), phenolics, hypoxanthine/xanthine oxidase assay.
TL;DR: From the ethyl acetate fraction of the methanol extract of the needles of Pinus densiflora, a new diterpenoid glucoside was isolated and characterized on the basis of spectral analysis and showed peroxynitrite scavenging activity.
Abstract: From the ethyl acetate fraction of the methanol extract of the needles of Pinus densiflora (Pinaceae), a new diterpenoid glucoside [9α,13α-epoxy-8β,14β-dihydroxy-abietic acid-18-O-β-d-glucopyranoside] (1), two flavonoid glucosides [kaempferol 3-O-β-d-glucoside (2) and 6-C-methyl kaempferol 3-O-β-d-glucoside (3)], and two monoterpenoid glucosides [bornyl 6-O-α-Larabinofuranosyl (1→6)-β-d-glucopyranoside (4) and bornyl 6-O-β-d-apiofuranosyl (1→6)-β-d-glucopyranoside (5)] were isolated and characterized on the basis of spectral analysis. Of all the compounds, 2 and 3 showed peroxynitrite scavenging activity.
TL;DR: The role of these flavonoids is discussed in this article, using a rapid and simple method, i.e. flavonoid histolocalization associated with UV, it was demonstrated that saw-wort contains high concentrations of luteolin derivatives and could be considered for use again as a natural dye.
TL;DR: In this article, the sesquiterpene glucoside carandoside (1) and (6S,7R,8R)-7a-[(β-glucopyranosyl)oxy]lyoniresinol (2) were isolated from the stem of Carissa carandas, together with three known lignans.
Abstract: Two new compounds, the sesquiterpene glucoside carandoside (1) and (6S,7R,8R)-7a-[(β-glucopyranosyl)oxy]lyoniresinol (2), were isolated from the stem of Carissa carandas, together with three known lignans. The structures of the isolated compounds were determined on the basis of spectroscopic evidence. Their DPPH free radical-scavenging activities were also evaluated.
TL;DR: A new cycle that includes newly discovered nicotinamide riboside deaminase which is also functional in potato tubers is found, and seems to be derived not only from the pyridine nucleotide cycle, but also from the de novo synthesis of nicotinic acid mononucleotide.
Abstract: As part of a research program on nucleotide metabolism in potato tubers (Solanum tuberosum L.), profiles of pyridine (nicotinamide) metabolism were examined based on the in situ metabolic fate of radio-labelled precursors and the in vitro activities of enzymes. In potato tubers, [3H]quinolinic acid, which is an intermediate of de novo pyridine nucleotide synthesis, and [14C]nicotinamide, a catabolite of NAD, were utilised for pyridine nucleotide synthesis. The in situ tracer experiments and in vitro enzyme assays suggest the operation of multiple pyridine nucleotide cycles. In addition to the previously proposed cycle consisting of seven metabolites, we found a new cycle that includes newly discovered nicotinamide riboside deaminase which is also functional in potato tubers. This cycle bypasses nicotinamide and nicotinic acid; it is NAD → nicotinamide mononucleotide → nicotinamide riboside → nicotinic acid riboside → nicotinic acid mononucleotide → nicotinic acid adenine dinucleotide → NAD. Degradation of the pyridine ring was extremely low in potato tubers. Nicotinic acid glucoside is formed from nicotinic acid in potato tubers. Comparative studies of [carboxyl-14C]nicotinic acid metabolism indicate that nicotinic acid is converted to nicotinic acid glucoside in all organs of potato plants. Trigonelline synthesis from [carboxyl-14C]nicotinic acid was also found. Conversion was greater in green parts of plants, such as leaves and stem, than in underground parts of potato plants. Nicotinic acid utilised for the biosynthesis of these conjugates seems to be derived not only from the pyridine nucleotide cycle, but also from the de novo synthesis of nicotinic acid mononucleotide.
TL;DR: Two new monoterpene glucoside minimaoside A and one new sesquiterpene glucose-like substance B showed weak or moderate cytotoxic activity toward several tumor cell lines and were determined by spectroscopic methods.
TL;DR: The thermal degradation of cyanidin 3-(6''-malonyl) glucoside and cyanidIn 3-glucoside, which are the two major anthocyanins in blood orange juice, have been investigated using the pH-differential method and RP-HPLC method, respectively.
Abstract: The thermal degradation of cyanidin 3-(6''-malonyl) glucoside and cyanidin 3-glucoside, which are the two major anthocyanins in blood orange juice, have been investigated using the pH-differential method and RP-HPLC method, respectively. Similar results could be obtained when the degradation kinetics of cyanidin 3-glucoside were studied by either the HPLC method or the pH-differential method. However, contrary results were obtained in the case of cyanidin 3-(6''-malonyl) glucoside. The HPLC analysis indicated that cyanidin 3-(6''-malonyl) glucoside was labile to eliminate a malonyl moiety to form cyanidin 3-glucoside before disappearing during thermal treatment and showed a lower thermal stability than cyanidin 3-glucoside, whereas the result obtained by the pH-differential method actually reflected the content of both cyanidin 3-(6''-malonyl) glucoside and its degradation intermediate. This caused an overestimate of the stability of cyanidin 3-(6''-malonyl) glucoside.
TL;DR: It is noteworthy that polygonophenone is the first naturally methoxyethoxymethyl (MEM)-substituted natural product, and its isolation gives support for the use of MEM protection in biomimetic synthetic schemes.
Abstract: An unprecedented natural acetophenone, polygonophenone (1), and a new resorcinol, polygonocinol (2), were isolated from the dichloromethane and methanol extracts of Polygonum maritimum and identified as 2-hydroxy-4-[(2-methoxyethoxy)methoxy] acetophenone and 2-methyl-5-nonadecylresorcinol, respectively. In addition, 11 known compounds were identified, namely, the sesquiterpenoid (+)-8-hydroxycalamene, four ferulic acid esters (tetracosyl, hexacosyl, octacosyl, and triacontyl ferulate), the arylpropane broussonin B, the flavonoids quercetin, quercitrin, and (+)-catechin, the hydroquinone glucoside isotachioside, and β-sitosterol. The structures of the new compounds were elucidated on the basis of their NMR and MS data. It is noteworthy that polygonophenone (1) is the first naturally methoxyethoxymethyl (MEM)-substituted natural product, and its isolation gives support for the use of MEM protection in biomimetic synthetic schemes.
Patent•
17 Sep 2009TL;DR: In this article, the present invention relates to compounds of formula I and pharmaceutically acceptable salts thereof, and to formulations and uses of the compounds of formulas of formula (I) in the treatment of metabolic disorders.
Abstract: The present invention relates to compounds of formula I and pharmaceutically acceptable salts thereof, and to formulations and uses of the compounds of formula (I) in the treatment of metabolic disorders.
TL;DR: Two new flavonoid glycosides were isolated from the leaves of Sterculia foetida L and a new phenylpropanoid glucose ester, 1,6-diferuloyl glucose, and their structures were elucidated by spectroscopic analysis and chemical evidence.
TL;DR: A new C-glucoside, 3,4-epoxy-5-hydroxymethyl benzoate 2-C-β-glocoside (1), together with a known alkaloid, 1H-indole-3-carbaldehyde (2), were isolated from the whole plant of Commelina communis L. as mentioned in this paper.
Abstract: A new C-glucoside, 3,4-epoxy-5-hydroxymethyl benzoate 2-C-β-glucoside (1), together with a known alkaloid, 1H-indole-3-carbaldehyde (2), were isolated from the whole plant of Commelina communis L. The structures of these compounds were determined by 1D, 2D NMR and MS techniques.
TL;DR: Three new sesquiterpene glucoside xianglinmaojuesides A-C were isolated from the aqueous extract of the aerial parts of Dryopteris fragrans (L.) schot by reversed-phase HPLC and their structures were elucidated by HRESIMS and 1D, 2D NMR analyses.
TL;DR: The phloroglucinol glucoside derivative, butan-1-one, roseoside, and kaempferol-3-O-β-D-glucopyranoside were isolated from the aerial parts of Conyza aegyptiaca, which is the first isolation of compounds 1 - 3 from C. aeEgyptiaca.
Abstract: 1 H- 1 H COSY, HMQC and HMBC experiments). The anti- oxidant activity of 1, using the DPPH assay, was investigated; in addition, 1 was investigated against different types of cell lines, including Hep-G2, HCT-116, and RAW 264.7 for its cytotoxic effects. Also, this is the fi rst report on the activity of 1.
TL;DR: Elaeagnoside (1), a new steroidal glucoside, has been isolated from the chloroform fraction of Elaeagnus orientalis along with β-sitosterol and 12-hydroxy-8,10-octadecadienoic acid and showed significant inhibitory activity against the enzyme chymotrypsin.
TL;DR: In this paper, the extraction of methyl orange or methylene blue from an aqueous phase to an organic phase of reverse micelles of alkyl glucosides was investigated.
Abstract: The extraction of methyl orange or methylene blue from an aqueous phase to an organic phase of reverse micelles of alkyl glucosides was investigated. Dodecyl glucoside, a biodegradable and biocompatible surfactant, was employed as a kind of alkyl glucosides, since a stable Winsor II system consisting of the water-in-oil type microemulsion and aqueous phases was formed when an organic solution containing dodecyl glucoside was contacted with an aqueous solution. The water content in the reverse micellar organic phase increased with an increase in the concentration of dodecyl glucoside. The extraction ratio of dyes also increased with increasing the concentration of dodecyl glucoside. Furthermore, the extraction ratio of dyes was dramatically dependent upon the pH of an aqueous phase and temperature.
TL;DR: Glucoamylase from Rhizopus mold and β-glucosidase catalysed synthesis of dopamine- d -glucose was optimized in terms of pH, buffer, enzyme, dopamine concentrations and incubation period in organic media as discussed by the authors.
TL;DR: In this paper, chemical constituents of the roots of Valeriana officinalis L. were isolated by various column chromatographic techniques and their structures were elucidated by spectroscopic methods.
TL;DR: As a result, this separated leaf cell suspension system was found to well reproduce the in vivo plant metabolism, and the metabolites were extensively transformed in cabbage, whereas they were scarcely metabolized in tomato.
Abstract: Metabolic profiles of 14C-labeled primary metabolites from several pesticides, 4-cyanophenol (1), 3-phenoxybenzoic acid (2), 3-phenoxybenzyl alcohol (3), 3,5-dichloroaniline (4), and (1RS)-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (5), were examined by using enzymatically separated leaf cell suspension from seedlings of cabbage (Brassica oleracea) and tomato (Lycopersicon esculentum). After 1 day of incubation, the metabolites were extensively transformed in cabbage, whereas they were scarcely metabolized in tomato. The major metabolic pathways were the phase II reactions leading to a number of conjugates such as glucoside/malonylglucoside of 1−5, malate of 2, and glutamate of 4. The oxidation of 1 and 2 was observed as a minor reaction to produce 4-hydroxybezoic acid and 3-(4-hydroxyphenoxy)benzoic acid. The chemical identities of the secondary metabolites were determined by various spectrometric analyses (LC-MS, LC-MS/MS, and NMR) and/or HPLC cochromatography with the synthet...
TL;DR: In this paper, a new flavonoid glucoside with a known one was isolated from the leaves of Cassia angustifolia, and their chemical structures were determined as kaempferol-3-O-[(6‴-O-trans-sinnapoyl)-β- d -glucopyranosyl (1 ǫ→ 6)]-β-d-glucophyranoside 1 and apigenin-6,8-di-C-glycoside 2.
TL;DR: Mutiniside, new phenolic glucoside, and the flavonoidal glucosides cephacoside have been isolated from the n-BuOH soluble fraction of Abutilon muticum and showed significant antioxidant activity while moderate inhibitory activity was observed against the enzyme lipoxygenase.