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Sample records for neuartige glycoside monosaccharide

  1. Influences of monosaccharides and its glycosidic linkage on infrared spectral characteristics of disaccharides in aqueous solutions.

    Science.gov (United States)

    Kanou, Mikihito; Nakanishi, Kenichi; Hashimoto, Atsushi; Kameoka, Takaharu

    2005-07-01

    The infrared spectral characteristics of ten different types of disaccharides (trehalose, kojibiose, nigerose, maltose, isomaltose, trehalulose, sucrose, turanose, maltulose, and palatinose) and five different types of monosaccharides (glucose, mannose, galactose, talose, and fructose) in aqueous solutions (H2O and D2O) were determined. The infrared spectra were collected using the Fourier transform infrared attenuated total reflectance (FT-IR/ATR) method and comparisons between the degrees of absorption band-shift of the saccharide spectra in the H2O solution with those in the D2O solution with respect to the saccharide concentrations were done. The study revealed that the wavenumber shifts in the bands of mono- and disaccharides in the H2O and D2O solutions could be used as an indicator of the level of interaction between the saccharides and water. The study also focused on the glycosidic linkage position and the constituent monosaccharides and found that they have a significant influence on the infrared spectroscopic characterization of disaccharides in an aqueous solution.

  2. Nickel-catalyzed proton-deuterium exchange (HDX) procedures for glycosidic linkage analysis of complex carbohydrates

    Science.gov (United States)

    The structural analysis of complex carbohydrates typically requires the assignment of three parameters: monosaccharide composition, the position of glycosidic linkages between monosaccharides, and the position and nature of non-carbohydrate substituents. The glycosidic linkage positions are often de...

  3. Carbohydrate analysis of hemicelluloses by gas chromatography-mass spectrometry of acteylated methyl glycosides

    DEFF Research Database (Denmark)

    Sárossy, Zsuzsa; Plackett, David; Egsgaard, Helge

    2012-01-01

    A method based on gas chromatography–mass spectrometry analysis of acetylated methyl glycosides was developed in order to analyze monosaccharides obtained from various hemicelluloses. The derivatives of monosaccharide standards, arabinose, glucose, and xylose were studied in detail and 13C-labele......-labeled analogues were used for identification and quantitative analysis. Excellent chromatographic separation of the monosaccharide derivatives was found and identification of the anomeric configuration was feasible through a prepared and identified pure methyl 2,3,4,6-tetra...

  4. Cellulase Inhibition by High Concentrations of Monosaccharides

    DEFF Research Database (Denmark)

    Hsieh, Chia-Wen; Cannella, David; Jørgensen, Henning

    2014-01-01

    that low free water availability contributes to cellulase inhibition. Of the hydrolytic enzymes involved, those acting on the cellulose substrate, that is, exo- and endoglucanases, were the most inhibited. The β -glucosidases were shown to be less sensitive to high monosaccharide concentrations except......Biological degradation of biomass on an industrial scale culminates in high concentrations of end products. It is known that the accumulation of glucose and cellobiose, end products of hydrolysis, inhibit cellulases and decrease glucose yields. Aside from these end products, however, other...

  5. Electron Impact Ion Fragmentation Pathways of Peracetylated C-glycoside Ketones Derived from Cyclic 1,3-diketones

    Science.gov (United States)

    Monosaccharide C-glycoside ketones have been prepared by aqueous-based Knoevenagel condensation of isotopically-labeled and unlabeled aldoses with cyclic diketones, 5,5-dimethyl-1,3-cyclohexanedione (dimedone) and 1,3-cyclohexanedione (1,3-CHD). The reaction products and their corresponding acetyla...

  6. Safety evaluation of the human-identical milk monosaccharide, l-fucose.

    Science.gov (United States)

    Choi, Sharon S H; Lynch, Barry S; Baldwin, Nigel; Dakoulas, Emily W; Roy, Shambhu; Moore, Carey; Thorsrud, Bjorn A; Röhrig, Christoph H

    2015-06-01

    l-Fucose is a natural monosaccharide present in mammals where it is found predominantly as an O-glycosidically linked component of glycoproteins, glycolipids, and oligosaccharides. It is also present in its free form in human breast milk (human milk monosaccharide). l-Fucose plays important roles in the development of the immune and nervous systems and is involved in cognitive function and memory formation. The human-identical milk monosaccharide l-fucose is therefore proposed for use in infant formulas to better simulate the free saccharides present in human breast milk. As part of the safety evaluation of l-fucose, a subchronic dietary toxicity study preceded by an in utero phase was conducted in Sprague-Dawley rats. l-Fucose was without maternal toxicity or compound-related adverse effects on female reproduction and general growth and development of offspring at a maternal dietary level up to 1%, equivalent to a dose of 1655 mg/kg body weight (bw)/day. During the subchronic phase, no compound-related adverse effects were observed in first generation rats at dietary levels of up to 1% (highest level tested), corresponding to doses of 516 and 665 mg/kg bw/day in males and females, respectively. l-Fucose was non-genotoxic in a series of in vitro genotoxicity/mutagenicity tests. These results support the safe use of l-fucose in infant formula and as a food ingredient at levels equivalent to those present in human breast milk. Copyright © 2015 Elsevier Inc. All rights reserved.

  7. Naturally occurring cardiac glycosides.

    Science.gov (United States)

    Radford, D J; Gillies, A D; Hinds, J A; Duffy, P

    1986-05-12

    Cardiac glycoside poisoning from the ingestion of plants, particularly of oleanders, occurs with reasonable frequency in tropical and subtropical areas. We have assessed a variety of plant specimens for their cardiac glycoside content by means of radioimmunoassays with antibodies that differ in their specificity for cardiac glycosides. Significant amounts of immunoreactive cardiac glycoside were found to be present in the ornamental shrubs: yellow oleander (Thevetia peruviana); oleander (Nerium oleander); wintersweet (Carissa spectabilis); bushman's poison (Carissa acokanthera); sea-mango (Cerbera manghas); and frangipani (Plumeria rubra); and in the milkweeds: redheaded cotton-bush (Asclepias curassavica); balloon cotton (Asclepias fruiticosa); king's crown (Calotropis procera); and rubber vine (Cryptostegia grandifolia). The venom gland of the cane toad (Bufo marinus) also contained large quantities of cardiac glycosides. The competitive immunoassay method permits the rapid screening of specimens that are suspected to contain cardiac glycosides. Awareness of the existence of these plant and animal toxins and their dangers allows them to be avoided and poisoning prevented. The method is also useful for the confirmation of the presence of cardiac glycosides in serum in cases of poisoning.

  8. Monosaccharide analysis of succulent leaf tissue in Aloe.

    Science.gov (United States)

    Grace, Olwen M; Dzajic, Amra; Jäger, Anna K; Nyberg, Nils T; Önder, Arife; Rønsted, Nina

    2013-09-01

    The succulent leaf mesophyll in Aloe species supports a burgeoning natural products industry, particularly in Africa. Comparative data necessary to prioritise species with economic potential have been lacking. To survey leaf mesophyll monosaccharide composition in the genus Aloe using a predictive phylogenetic approach. Monosaccharide composition was assessed in 31 species, representing the morphological and taxonomic diversity of Aloe sensu stricto. Leaf mesophyll polysaccharides were partially hydrolysed in a trifluoroacetic acid (TFA)-SilA assay. Oximes and trimethylsilyl ether products were detected by GC-MS. Constituent monosaccharides accounting for the greatest variation among species were identified by principal component analysis. Two plant DNA barcoding regions were sequenced in 28 of the sampled species and the resulting maximum likelihood tree was used to evaluate phylogenetic signal in monosaccharide composition throughout the genus. Nineteen peaks (Rt=16.76-23.67 min) were identified in the GC-MS spectra. All samples were dominated by one constituent; glucose was the major monosaccharide in 19 species, mannose in eight species, and xylose in one species (Aloidendron pillansii). Three monosaccharides therefore account for 90% of the variation in leaf mesophyll in Aloe. Species which do not share this typical monosaccharide profile appear to group outside the core Aloe clade in the phylogeny. Preliminary findings suggest that leaf mesophyll monosaccharide composition is conservative in Aloe. Characterisation of within-species variation and quantitative differences between species will be necessary to authenticate leaf mesophyll products, whereas unusual monosaccharide profiles could be diagnostic in some species. The common glucose-mannose-xylose profile identified in commercially important species is shared by many other Aloe species. Crown Copyright © 2013. Published by Elsevier Ltd. All rights reserved.

  9. Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

    Science.gov (United States)

    Mondol, Muhammad Abdul Mojid; Shin, Hee Jae; Rahman, M. Aminur; Islam, Mohamad Tofazzal

    2017-01-01

    Sea cucumbers belonging to echinoderm are traditionally used as tonic food in China and other Asian countries. They produce abundant biologically active triterpene glycosides. More than 300 triterpene glycosides have been isolated and characterized from various species of sea cucumbers, which are classified as holostane and nonholostane depending on the presence or absence of a specific structural unit γ(18,20)-lactone in the aglycone. Triterpene glycosides contain a carbohydrate chain up to six monosaccharide units mainly consisting of d-xylose, 3-O-methy-d-xylose, d-glucose, 3-O-methyl-d-glucose, and d-quinovose. Cytotoxicity is the common biological property of triterpene glycosides isolated from sea cucumbers. Besides cytotoxicity, triterpene glycosides also exhibit antifungal, antiviral and hemolytic activities. This review updates and summarizes our understanding on diverse chemical structures of triterpene glycosides from various species of sea cucumbers and their important biological activities. Mechanisms of action and structural–activity relationships (SARs) of sea cucumber glycosides are also discussed briefly. PMID:29039760

  10. Neutral monosaccharides in surface sediments of the northwestern Mediterranean Sea

    Energy Technology Data Exchange (ETDEWEB)

    Kerherve, P.; Buscail, R.; Gadel, F. [Universite de Perpignan (France). Centre de Formation et de Recherche sur l' Environnement Marin; Serve, L. [Universite de Perpignan (France). Laboratoire de Biologie Physico-Chimique des Systemes Integres

    2002-07-01

    This paper is focused on carbohydrates, an abundant chemical class in marine organic matter, mostly found as polysaccharides. An experiment showed that the use of H{sub 2}SO{sub 4} 1 M (95{sup o}C, 4 h) yielded a good compromise between recovery and degradation of all neutral monosaccharides from two kinds of organic material: surface sediments and trapped particles. Twenty samples of surface sediments (0-0.5 cm) were collected in various physiographic and bathymetric locations on the Northwestern Mediterranean margin. Neutral monosaccharides were determined by an ionic chromatography system with electrochemical detection (HPAEC-PAD). Differences between total neutral monosaccharides (NM{sub TOT}) and total carbohydrates, determined by a spectrophotometric method on the same samples, brought further assumptions on the nature of the carbohydrate pool. Total neutral monosaccharides contents varied from 0.46 to 1.04 mg g{sup -1} and their proportions donated to the organic carbon pool (NM{sub TOT}-C/OC) barely reached 5%. The spatial distribution of NM{sub TOT} and organic carbon (OC) clearly showed that organic inputs, originating from the shallower epicontinental area, spread along canyon axis while undergoing dilution processes. In spite of the high physiographic and bathymetric diversity, surface sediments from most stations were characterized markedly by the homogeneity in the neutral monosaccharide compositions. Two stations, E21 (Ebro prodelta) and EC36 (Balearic slope) showed, however, distinct signatures with high relative abundances of glucose and galactose, respectively. Glucose was found to trace the continental inputs, whereas galactose characterized the marine inputs. The relative 'freshness' of the organic material at station EC36, assumed by the high proportion of hexose neutral monosaccharides, confirms the dominance of phytoplankton remains at this station. This work showed that the use of monosaccharides as tracers of the biological source

  11. Growth and enzyme production by three Penicillium species on monosaccharides

    DEFF Research Database (Denmark)

    Jørgensen, Henning; Krogh, Astrid Mørkeberg; Krogh, Kristian Bertel Rømer

    2004-01-01

    The growth and preference for utilisation of various sugar by the Penicillium species Penicillium pinophilum IBT 4186, Penicillium persicinum IBT 13226 and Penicillium brasilianum IBT 20888 was studied in batch cultivations using various monosaccharides as carbon source, either alone or in mixtures...

  12. Monosaccharide analysis of succulent leaf tissue in Aloe

    DEFF Research Database (Denmark)

    Grace, Olwen Megan; Dzajic, Amra; Jäger, Anna

    2013-01-01

    . Oximes and trimethylsilyl ether products were detected by GC-MS. Constituent monosaccharides accounting for the greatest variation among species were identified by principal component analysis. Two plant DNA barcoding regions were sequenced in 28 of the sampled species and the resulting maximum...

  13. Effects of different monosaccharides on histamine-stimulated gastric ...

    African Journals Online (AJOL)

    Monosaccharides such as glucose, fructose and galactose have been established as the main energy source for physiological activities in the body. The current study was undertaken to investigate the effects of different monosaccarides on histamine-stimulated gastric acid secretion and also to investigate whether acute ...

  14. Variants of glycoside hydrolases

    Energy Technology Data Exchange (ETDEWEB)

    Teter, Sarah; Ward, Connie; Cherry, Joel; Jones, Aubrey; Harris, Paul; Yi, Jung

    2017-07-11

    The present invention relates to variants of a parent glycoside hydrolase, comprising a substitution at one or more positions corresponding to positions 21, 94, 157, 205, 206, 247, 337, 350, 373, 383, 438, 455, 467, and 486 of amino acids 1 to 513 of SEQ ID NO: 2, and optionally further comprising a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2 a substitution at one or more positions corresponding to positions 8, 22, 41, 49, 57, 113, 193, 196, 226, 227, 246, 251, 255, 259, 301, 356, 371, 411, and 462 of amino acids 1 to 513 of SEQ ID NO: 2, wherein the variants have glycoside hydrolase activity. The present invention also relates to nucleotide sequences encoding the variant glycoside hydrolases and to nucleic acid constructs, vectors, and host cells comprising the nucleotide sequences.

  15. Effect of dietary monosaccharides on Pseudomonas aeruginosa virulence.

    Science.gov (United States)

    Nelson, Ryan K; Poroyko, Valeriy; Morowitz, Michael J; Liu, Don; Alverdy, John C

    2013-02-01

    Pseudomonas aeruginosa is an opportunistic, gram-negative pathogen associated with many hospital-acquired infections and disease states. In particular, P. aeruginosa has been identified as a crucial factor in the pathogenesis of neonatal necrotizing enterocolitis (NEC). This condition presents more frequently in infants fed a formula-based diet, which may be a result of the specific monosaccharide content of this diet. We hypothesized that P. aeruginosa would express virulence genes differentially when exposed to monosaccharides present in formula versus those in human milk. Using the results of a metabolomics study on infant diets and their resulting fecal samples, we identified several monosaccharides that distinguished milk from formula diets. Of these compounds, four were found to be metabolized by P. aeruginosa. We subsequently grew P. aeruginosa in tryptic soy broth (TSB) supplemented with these four monosaccharides and used quantitative reverse transcriptase-polymerase chain reaction to measure the expression of 59 major P. aeruginosa virulence genes. The results were standardized to an external control of P. aeruginosa grown in TSB alone. P. aeruginosa did not respond differentially to the monosaccharides after 6 h of growth. However, after 24 h, the organism grown in arabinose (present in formula), xylose (present in human milk), and galactose (present in both formula and feces from milk-fed infants) displayed a significant increase in the expression of virulence genes in all categories. In contrast, P. aeruginosa grown in mannose (present in the feces of milk-fed infants) displayed a significant decrease in virulence gene expression. These results demonstrate the importance of nutrient content on the relative expression of virulence genes in pathogens that colonize commonly the gut of infants. Understanding the effect of current dietary formulas on virulence gene expression in various gut-colonizing pathogens may present a new approach to elucidating the

  16. Glycosides from Bougainvillea glabra.

    Science.gov (United States)

    Simon, András; Tóth, Gábor; Duddeck, Helmut; Soliman, Hesham S M; Mahmoud, Ibrahim I; Samir, Hanan

    2006-01-01

    Three glycosides were isolated from Bougainvillea glabra and their structures were determined by extensive use of 1D and 2D NMR spectroscopy ((1)H and (13)C). First compound was identical to momordin IIc (quinoside D) [beta-D-glucopyranosyl 3-O-[beta-D-xylopyranosyl-(1 --> 3)-O-(beta-D-glucopyranosyluronic acid)] oleanolate], second compound was quercetin 3-O-alpha-L-(rhamnopyranosyl)(1 --> 6)-[alpha-L-rhamnopy-ranosyl(1 --> 2)]-beta-D-galactopyranoside and third compound was its derivative quercetin 3-O-alpha-L-(4-caffeoylrhamnopyranosyl)(1 --> 6)-[alpha-L-rhamnopyranosyl (1 --> 2)]-beta-D-galactopyranoside, a new natural product.

  17. Cyanohydrin glycosides of Passiflora

    DEFF Research Database (Denmark)

    Jaroszewski, Jerzy W; Olafsdottir, Elin S; Wellendorph, Petrine

    2002-01-01

    Nineteen species of Passiflora (Passifloraceae) were examined for the presence of cyanogenic glycosides. Passibiflorin, a bisglycoside containing the 6-deoxy-beta-D-gulopyranosyl residue, was isolated from P. apetala, P. biflora, P. cuneata, P. indecora, P. murucuja and P. perfoliata. In some cas......-hydroxyamides to cyanohydrins that liberate cyanide; this finding is of interest in connection with analysis of plant tissues and extracts using Helix pomatia enzymes....... Passiflora species. These alpha-hydroxyamides, presumably formed during processing of the plant material, behave as cyanogenic compounds when treated with commercial Helix pomatia crude enzyme preparation. Thus, the enzyme preparation appears to contain an amide dehydratase, which converts alpha...

  18. Monosaccharides in the water of the Gulf of Gdansk

    Directory of Open Access Journals (Sweden)

    Waldemar Grzybowski

    2001-06-01

    Full Text Available The concentration of monosaccharides in samples collected in the Gulf of Gdansk area was determined in water filtered through ~0.8 µm pore size filters. Seawater concentrations ranged from about 0.2 to 1.1 mg C dm-3, the highest values being detected at the mouth of the river Vistula. Seasonality was detectable in the data distribution; the majority of autumn values lay within the 0.2–0.4 range while concentrations in the spring samples were higher and the values more widely scattered. Measurements of monosaccharide concentrations at selected points during the whole observation period showed that values increased from spring to autumn as much as 5-fold. Concomitant analyses in Vistula river water yielded concentrations from 0.4 to 1.2 mg C dm-3. These latter values were all higher than those recorded in seawater in the corresponding months.

  19. Galactan synthesis in a single step via oligomerization of monosaccharides

    Directory of Open Access Journals (Sweden)

    Marius Dräger

    2014-11-01

    Full Text Available Galactans ranging in length from one to five residues were prepared in a single step by treatment of the glycosyl donor 2,3,4-tri-O-benzoyl-β-D-galactopyranosyl fluoride with lanthanum perchlorate in the presence of an initiator alcohol. The product oligosaccharides were readily chromatographically separable. This oligomerization was used to synthesize a pentagalactan in a single step from monosaccharide building blocks in reasonable overall yields.

  20. Monosaccharide-NAIM Derivatives for D-, L-Configurational Analysis

    Directory of Open Access Journals (Sweden)

    Chunchi Lin

    2011-01-01

    Full Text Available The D-, L-enantiomeric pairs of common monosaccharides (xylose, ribose, rhamnose, arabinose, fucose, glucose, mannose, galactose, N-acetylgalactosamine, glucuronic acid and galacturonic acid were derivatized with 2,3-naphthalenediamine to form the corresponding D-, L-aldo-NAIM derivatives. A simple and facile capillary electrophoretic method was established for sugar composition analysis by simultaneously determining the migration times of these aldo-NAIMs using borate buffer at high pH (100 mM, pH 9.0. The methodology is also applicable to sialic acid (ketose monosaccharides. The quantitation level of the proposed method was in the 10~500 ppm range and the LOD was 1 ppm. The enantioseparation of D, L pairs of aldo-NAIMs were also achieved by using modified sulfated-a-cyclodextrin as the chiral selector in phosphate buffer (300 mM, pH 3.0. In addition, the combination by reductive amination of amino-aldo-NAIM agent and D-, L-enantiomeric pairs of monosaccharides formed a diastereomeric pair for saccharide configuration analysis. Aldo-NAIM derivatives are thus shown to be rapid and efficient agents for analyzing saccharide compositions and configurations with good linearity and short analysis times via capillary electrophoresis.

  1. Phenylethanoid glycosides from Stachys officinalis.

    Science.gov (United States)

    Miyase, T; Yamamoto, R; Ueno, A

    1996-09-01

    From the aerial parts of Stachys officinalis, six new phenylethanoid glycosides, named betonyosides A-F, and six known phenylethanoid glycosides, acetoside, acetoside isomer, campneosides II, forsythoside B and leucosceptoside B, were isolated and their structures were elucidated from spectroscopic and chemical evidence. Campneosides II were separated into two epimers.

  2. Glycoside vs. Aglycon: The Role of Glycosidic Residue in Biological Activity

    Science.gov (United States)

    Křen, Vladimír

    A large number of biologically active compounds are glycosides. Sometimes the glycosidic residue is crucial for their activity, in other cases glycosylation only improves pharmacokinetic parameters. Recent developments in molecular glycobiology brought better understanding of aglycon vs. glycoside activities, and made possible the development of new, more active or more effective glycodrugs based on these findings - a very illustrative recent example is vancomycin. The new enzymatic methodology "glycorandomization" enabled preparation of glycoside libraries and opened up paths to the preparation of optimized or entirely novel glycoside antibiotics. This chapter deals with an array of glycosidic compounds currently used in medicine but also covers the biological activity of some glycosidic metabolites of known drugs. The chapter discusses glycosides of vitamins, polyphenolic glycosides (flavonoids), alkaloid glycosides, glycosides of antibiotics, glycopeptides, cardiac glycosides, steroid and terpenoid glycosides etc. The physiological role of the glycosyl moiety and structure-activity relations (SAR) in the glycosidic moiety (-ies) are also discussed.

  3. Monosaccharide transport into hemocytes of a sipunculan worm Themiste dyscrita

    Energy Technology Data Exchange (ETDEWEB)

    Ingermann, R.L.; Hall, R.E.; Bissonnette, J.M.; Terwilliger, R.C.

    1985-07-01

    The hemerythrin-containing blood cells, or hemocytes, of the sipunculan worm Themiste dyscrita were found to have a stereospecific and nonconcentrative monosaccharide transport system. The transport system transferred both D-glucose and 3-O-methyl-D-glucose (3-OMG), and transport into cells by this system was rapid, reaching 50% equilibrium in approximately 20 s at 10 degrees C with an initial concentration gradient of 0.1 mM; the contribution to total uptake by simple diffusion was very small. 3-OMG uptake showed saturation kinetics with a low half-saturation constant (Km less than or equal to 0.1 mM). The uptake of labeled 3-OMG by the hemocytes was strongly inhibited by unlabeled 3-OMG, 2-deoxy-D-glucose, alpha- and beta-D-glucose, D-galactose, and D-mannose. It was moderately inhibited by D-xylose, only slightly by alpha-methyl-D-glucoside and D-fructose, and uninhibited by sucrose, L-glucose, or D-sorbitol. Phloretin was more potent than phloridzin in blocking entry of 3-OMG. Cytochalasin B did not bind tightly to the T. dyscrita transporter and was not a potent inhibitor of transport; it half-maximally inhibited 3-OMG transport at 0.1 mM. Therefore, despite some differences the data suggest functional similarities in the mechanism of monosaccharide transport into blood cells of mammals and this invertebrate.

  4. Estimation of monosaccharide radioactivity in biological samples through osazone derivatization

    Energy Technology Data Exchange (ETDEWEB)

    Garcia, F.J.; Pons, A.; Alemany, M.; Palou, A.

    1982-03-01

    A method for the quantitative estimation of radioactivity in the glucose (monosaccharide) fraction of biological samples is presented. Radioactive samples are added with cold glucose, and 1 aliquot receives a known amount of radioactive glucose as internal standard. After controlled osazone formation and three washings of the yellow precipitate, the osazones are dissolved, decolored, and their radioactivity determined through scintillation counting. The overall efficiency of recovery is 23-24% of the initial readioactivity. Each sample is corrected by the recovery of its own internal standard. There is a very close linear relationship between radioactivity present in the samples and radioactivity found, despite the use of different biological samples (rat plasma, hen egg yolk and albumen).

  5. Carbon isotope variability in monosaccharides and lipids of aquatic algae and terrestrial plants

    NARCIS (Netherlands)

    Sinninghe Damsté, J.S.; Dongen, B.E. van; Schouten, S.

    2002-01-01

    The stable carbon-isotope compositions of individual monosaccharides and lipids, as well as the bulk stable carbon-isotope composition of total cell material from different aquatic and terrestrial plants were determined. With the exception of a Phaeocystis sp. bloom sample, monosaccharides were

  6. The effect of cathodic polarisation on monosaccharides of Amphora coffeaeformis, a marine fouling diatom

    Digital Repository Service at National Institute of Oceanography (India)

    Bhosle, N.B.; Evans, L.V.; Edyvean, R.G.J.

    , concentrations of monosaccharides were higher by a factor of 8 to 40 in A. coffeaeformis cells attached to non-polarised steel. The abundance of monosaccharides increased over the period of cultivation in the cells on non-polarised steel. Eight individual...

  7. Electricity production from twelve monosaccharides using microbial fuel cells

    Science.gov (United States)

    Catal, Tunc; Li, Kaichang; Bermek, Hakan; Liu, Hong

    Direct generation of electricity from monosaccharides of lignocellulosic biomass was examined using air cathode microbial fuel cells (MFCs). Electricity was generated from all carbon sources tested, including six hexoses (D-glucose, D-galactose, D(-)-levulose (fructose), L-fucose, L-rhamnose, and D-mannose), three pentoses (D-xylose, D(-)-arabinose, and D(-)-ribose), two uronic acids (D-galacturonic acid and D-glucuronic acid) and one aldonic acid (D-gluconic acid). The mixed bacterial culture, which was enriched using acetate as a carbon source, adapted well to all carbon sources tested, although the adaptation times varied from 1 to 70 h. The maximum power density obtained from these carbon sources ranged from 1240 ± 10 to 2770 ± 30 mW m -2 at current density range of 0.76-1.18 mA cm -2. D-Mannose resulted in the lowest maximum power density, whereas D-glucuronic acid generated the highest one. Coulombic efficiency ranged from 21 to 37%. For all carbon sources tested, the relationship between the maximum voltage output and the substrate concentration appeared to follow saturation kinetics at 120 Ω external resistance. The estimated maximum voltage output ranged between 0.26 and 0.44 V and half-saturation kinetic constants ranged from 111 to 725 mg L -1. Chemical oxygen demand (COD) removal was over 80% for all carbon sources tested. Results from this study indicated that lignocellulosic biomass-derived monosaccharides might be a suitable resource for electricity generation using MFC technology.

  8. Electricity production from twelve monosaccharides using microbial fuel cells

    Energy Technology Data Exchange (ETDEWEB)

    Catal, Tunc [Department of Biological and Ecological Engineering, Oregon State University, 116 Gilmore Hall, Corvallis, OR 97331 (United States); Department of Wood Science and Engineering, Oregon State University, 102 Richardson Hall, Corvallis, OR 97331 (United States); Department of Molecular Biology and Genetics, Istanbul Technical University, 34469-Maslak, Istanbul (Turkey); Li, Kaichang [Department of Wood Science and Engineering, Oregon State University, 102 Richardson Hall, Corvallis, OR 97331 (United States); Bermek, Hakan [Department of Molecular Biology and Genetics, Istanbul Technical University, 34469-Maslak, Istanbul (Turkey); Liu, Hong [Department of Biological and Ecological Engineering, Oregon State University, 116 Gilmore Hall, Corvallis, OR 97331 (United States)

    2008-01-03

    Direct generation of electricity from monosaccharides of lignocellulosic biomass was examined using air cathode microbial fuel cells (MFCs). Electricity was generated from all carbon sources tested, including six hexoses (D-glucose, D-galactose, D(-)-levulose (fructose), L-fucose, L-rhamnose, and D-mannose), three pentoses (D-xylose, D(-)-arabinose, and D(-)-ribose), two uronic acids (D-galacturonic acid and D-glucuronic acid) and one aldonic acid (D-gluconic acid). The mixed bacterial culture, which was enriched using acetate as a carbon source, adapted well to all carbon sources tested, although the adaptation times varied from 1 to 70 h. The maximum power density obtained from these carbon sources ranged from 1240 {+-} 10 to 2770 {+-} 30 mW m{sup -2} at current density range of 0.76-1.18 mA cm{sup -2}. D-Mannose resulted in the lowest maximum power density, whereas D-glucuronic acid generated the highest one. Coulombic efficiency ranged from 21 to 37%. For all carbon sources tested, the relationship between the maximum voltage output and the substrate concentration appeared to follow saturation kinetics at 120 {omega} external resistance. The estimated maximum voltage output ranged between 0.26 and 0.44 V and half-saturation kinetic constants ranged from 111 to 725 mg L{sup -1}. Chemical oxygen demand (COD) removal was over 80% for all carbon sources tested. Results from this study indicated that lignocellulosic biomass-derived monosaccharides might be a suitable resource for electricity generation using MFC technology. (author)

  9. Analysis of the monosaccharide composition of fucoidan by precolumn derivation HPLC

    Science.gov (United States)

    Zhang, Jingjing; Zhang, Quanbin; Wang, Jing; Shi, Xuelian; Zhang, Zhongshan

    2009-09-01

    We developed an HPLC method for analysis of the monosaccharide composition of fucoidans. The fucoidan was hydrolyzed into monosaccharides with 2 mol/L trifluoroacetic acid. Using ribose as the internal standard, the monosaccharide derivatives, obtained with 1-Phenyl-3-methyl-5-pyrazolone (PMP), were separated by reverse-phase HPLC using a gradient elution process, and monitored by ultraviolet detection at 245 nm. In the concentration range of 0.1-2.0 mmol/L, the peak area of each monosaccharide had a good linear relationship with its concentration ( r 2>0.998). The average recoveries of mannose, rhamnose, glucuronic acid, glucose, galactose, xylose, and fucose were 86.2%, 95.1%, 62.5%, 102.0%, 94.8%, 66.6%, and 105.1%, respectively. This method was accurate and had good reproducibility and could be used to determine the monosaccharide contents of fucoidans.

  10. Phenyl and phenylethyl glycosides from Picrorhiza scrophulariiflora.

    Science.gov (United States)

    Zou, Xu; Liao, Xun; Ding, Li-Sheng; Peng, Shu-Lin

    2007-01-01

    A new phenyl glycoside, scrophenoside D (1) and a new phenylethyl glycoside, scroside F (2), together with three known phenylethyl glycosides, scroside A (3), plantainoside D (4), and plantamajoside (5), were isolated from the stems of Picrorhiza scrophulariiflora. Their structures were elucidated by spectroscopic and chemical methods.

  11. Acylated flavone glycosides from Veronica

    DEFF Research Database (Denmark)

    Albach, Dirk C.; Grayer, Renée J.; Jensen, Søren Rosendal

    2003-01-01

    A survey of the flavonoid glycosides of selected taxa in the genus Veronica yielded two new acylated 5,6,7,3',4'-pentahydroxyflavone (6-hydroxyluteolin) glycosides and two rare allose-containing acylated 5,7,8,4'-tetrahydroxyflavone (isoscutellarein) glycosides. The new compounds were isolated fr...

  12. Carbon allocation in ectomycorrhizas: identification and expression analysis of an Amanita muscaria monosaccharide transporter.

    Science.gov (United States)

    Nehls, U; Wiese, J; Guttenberger, M; Hampp, R

    1998-03-01

    Ectomycorrhizas are formed between certain soil fungi and fine roots of predominantly woody plants. An important feature of this symbiosis is the supply of plant-derived carbohydrates to the fungus. As a first step toward a better understanding of the molecular basis of this process, we cloned a monosaccharide transporter from the ectomycorrhizal fungus Amanita muscaria. Degenerate oligonucleotide primers were designed to match conserved regions from known fungal sugar transporters. A cDNA fragment of the transporter was obtained from mycorrhizal mRNA by reverse transcription-polymerase chain reaction. This fragment was used to identify a clone (AmMst1) encoding the entire monosaccharide transporter in a Picea abies/A. muscaria mycorrhizal cDNA library. The cDNA codes for an open reading frame of 520 amino acids, showing best homology to a Neurospora crassa monosaccharide transporter. The function of AmMST1 as monosaccharide transporter was confirmed by heterologous expression of the cDNA in a Schizosaccharomyces pombe mutant lacking a monosaccharide uptake system. AmMst1 was constitutively expressed in fungal hyphae under all growth conditions. Nevertheless, in mycorrhizas as well as in hyphae grown at monosaccharide concentrations above 5 mM, the amount of AmMst1 transcript increased fourfold. We therefore suggest that AmMst1 is upregulated in ectomycorrhizas by a monosaccharide-controlled mechanism.

  13. Mechanistic understanding of monosaccharide-air flow battery electrochemistry

    Science.gov (United States)

    Scott, Daniel M.; Tsang, Tsz Ho; Chetty, Leticia; Aloi, Sekotilani; Liaw, Bor Yann

    Recently, an inexpensive monosaccharide-air flow battery configuration has been demonstrated to utilize a strong base and a mediator redox dye to harness electrical power from the partial oxidation of glucose. Here the mechanistic understanding of glucose oxidation in this unique glucose-air power source is further explored by acid-base titration experiments, 13C NMR, and comparison of results from chemically different redox mediators (indigo carmine vs. methyl viologen) and sugars (fructose vs. glucose) via studies using electrochemical techniques. Titration results indicate that gluconic acid is the main product of the cell reaction, as supported by evidence in the 13C NMR spectra. Using indigo carmine as the mediator dye and fructose as the energy source, an abiotic cell configuration generates a power density of 1.66 mW cm -2, which is greater than that produced from glucose under similar conditions (ca. 1.28 mW cm -2). A faster transition from fructose into the ene-diol intermediate than from glucose likely contributed to this difference in power density.

  14. Simultaneous analysis of neutral monosaccharides, fatty acids and cholesterol as biomarkers from a drop of blood.

    Science.gov (United States)

    Ciucanu, Ionel; Pilat, Luminiţa; Ciucanu, Cristian I; Şişu, Eugen; Dumitraşcu, Victor

    2016-10-01

    We have developed a method for simultaneous monitoring of more biomarkers from three different classes of compounds by simultaneous analysis of neutral monosaccharides, fatty acids (FAs) and cholesterol as their per-O-methylated derivatives from a drop of blood by GC-MS. This work is a development of our previous results about analysis of neutral monosaccharides from a drop of blood. The simultaneous per-O-methylation was obtained by methylation in one step with methyl iodide and NaOH in DMSO. The per-O-methylated derivatives were separated in one chromatogram. The quantitative analysis was reproducible for five monosaccharides, 22 FAs and cholesterol. The results of this method were compared with those of the enzymatic methods using commercial kits. This method can avoid the saponification of the FA methyl esters and can analyze for the first time simultaneously neutral monosaccharides, FAs and cholesterol from a drop of blood.

  15. Diterpene Glycosides from Stevia rebaudiana

    Directory of Open Access Journals (Sweden)

    Indra Prakash

    2011-04-01

    Full Text Available Three novel diterpene glycosides were isolated for the first time from the commercial extract of the leaves of Stevia rebaudiana, along with several known steviol glycosides, namely stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy] ent-kaur-15-en-19-oic acid (1, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy]-16β-hydroxy-ent-kauran-19-oic acid (2 and 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-β-D-glucopyranosyl ester (3 on the basis of extensive 2D NMR and MS spectroscopic data as well as chemical studies.

  16. Diterpene glycosides from Stevia rebaudiana.

    Science.gov (United States)

    Chaturvedula, Venkata Sai Prakash; Upreti, Mani; Prakash, Indra

    2011-04-28

    Three novel diterpene glycosides were isolated for the first time from the commercial extract of the leaves of Stevia rebaudiana, along with several known steviol glycosides, namely stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-15-en-19-oic acid, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-16β-hydroxy-ent-kauran-19-oic acid and 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-β-D-glucopyranosyl ester on the basis of extensive 2D NMR and MS spectroscopic data as well as chemical studies.

  17. Flavonoid glycosides from Barringtonia acutangula.

    Science.gov (United States)

    Vien, Le Thi; Van, Quach Thi Thanh; Hanh, Tran Thi Hong; Huong, Phan Thi Thanh; Thuy, Nguyen Thi Kim; Cuong, Nguyen The; Dang, Nguyen Hai; Thanh, Nguyen Van; Cuong, Nguyen Xuan; Nam, Nguyen Hoai; Kiem, Phan Van; Minh, Chau Van

    2017-08-15

    Using various chromatographic separation techniques, ten flavonoid glycosides, including six new compounds namely barringosides A-F (1-6), were isolated from a methanol extract of the Barringtonia acutangula leaves. The structure elucidation was confirmed by spectroscopic analyses, including 1D and 2D NMR, and HR ESI MS. Their inhibitory effects on LPS-induced NO production in RAW264.7 cells were also evaluated. Among the isolated compounds, quercetin 3-O-β-d-(6-p-hydroxybenzoyl)galactopyranoside (9) showed significant effect with an IC50 of 20.00±1.68µM. This is the first report of these flavonoid glycosides from Barringtonia genus and their inhibition on LPS-induced NO production in RAW264.7 cells was reported here for the first time. Copyright © 2017 Elsevier Ltd. All rights reserved.

  18. Steroidal glycosides from Ruscus ponticus.

    Science.gov (United States)

    Napolitano, Assunta; Muzashvili, Tamar; Perrone, Angela; Pizza, Cosimo; Kemertelidze, Ether; Piacente, Sonia

    2011-05-01

    A comparative metabolite profiling of the underground parts and leaves of Ruscus ponticus was obtained by an HPLC-ESIMS(n) method, based on high-performance liquid chromatography coupled to electrospray positive ionization multistage ion trap mass spectrometry. The careful study of HPLC-ESIMS(n) fragmentation pattern of each chromatographic peak, in particular the identification of diagnostic product ions, allowed us to get a rapid screening of saponins belonging to different classes, such as dehydrated/or not furostanol, spirostanol and pregnane glycosides, and to promptly highlight similarities and differences between the two plant parts. This approach, followed by isolation and structure elucidation by 1D- and 2D-NMR experiments, led to the identification of eleven saponins from the underground parts, of which two dehydrated furostanol glycosides and one new vespertilin derivative, and nine saponins from R. ponticus leaves, never reported previously. The achieved results highlighted a clean prevalence of furostanol glycoside derivatives in R. ponticus leaves rather in the underground parts of the plant, which showed a wider structure variety. In particular, the occurrence of dehydrated furostanol derivatives, for the first time isolated from a Ruscus species, is an unusual finding which makes unique the saponins profile of R. ponticus. Copyright © 2011 Elsevier Ltd. All rights reserved.

  19. Monosaccharides as Scaffolds for the Synthesis of Novel Compounds

    Science.gov (United States)

    Murphy, Paul V.; Velasco-Torrijos, Trinidad

    This chapter focuses on monosaccharides and scaffolds their derivatives as scaffolds for the synthesis of primarily bioactive compounds. Such carbohydrate derivatives have been designed to modulate mainly protein-protein and peptide-protein interactions although modulators of carbohydrate-protein and carbohydrate-nucleic acid interactions have also been of interest. The multiple hydroxyl groups that are present on saccharides have made pyranose, furanose and iminosugars ideal templates or scaffolds to which recognition or pharmacophoric groups can be grafted to generate novel compounds for medicinal chemistry. The synthesis of compounds for evaluations require strategies for regioselective reactions of saccharide hydroxyl groups and use of orthogonally stable protecting groups. Syntheses have been carried out on the solid phase and in solution. Also the use of uronic acids, amino sugars and sugar amino acids has facilitated the synthesis of peptidomimetics and prospecting libraries as they enable, through presence of amino or carboxylic acid groups, chemoselective approaches to be employed in solution and on solid phase. Sugar amino acids are readily incorporated, as peptide isosteres, to generate sugar-peptide hybrids or for the synthesis of novel carbopeptoids . The synthesis of new cyclic compounds, derived in part from saccharides, and their application as scaffolds is an emerging area and recent examples include spirocyclic compounds, benzodiazepine-saccharide hybrids and macrolide-saccharide hybrids. Potent bioactive saccharide derivatives have been identified that include enzyme inhibitors , somatostatin receptor ligands, integrin ligands, anti-viral compounds, shiga toxin inhibitors and cell growth inhibitors. Some saccharide derivatives have demonstrated improved cellular permeability when compared with peptides and are in clinical trials.

  20. New lignan glycosides from Justicia procumbens.

    Science.gov (United States)

    Jin, Hong; Yang, Shu; Dong, Jun-Xing

    2017-01-01

    Four new lignan glycosides (1-4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6-10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.

  1. STEROIDAL GLYCOSIDES FROM THE ROOTS OF SOLANUM MELONGENA L.

    Directory of Open Access Journals (Sweden)

    Stepan Shvets

    2009-12-01

    Full Text Available One new cholestane glycoside, six steroidal glycosides of spirostane series and one pregnane glycoside have been isolated from the roots of Solanum melongena L. for the first time. Their structures were determined by physico-chemical methods.

  2. A case of nondigitalis cardiac glycoside toxicity.

    Science.gov (United States)

    Gupta, A; Joshi, P; Jortani, S A; Valdes, R; Thorkelsson, T; Verjee, Z; Shemie, S

    1997-12-01

    A case is presented of cardiac glycoside poisoning in a 1-year-old patient from the plant Nerium oleander (common oleander). The patient had bradycardia, vomiting, altered level of consciousness, and no history of ingestion. Antibody-based digoxin assays may cross-react with other cardiac glycosides nonquantitatively. Chromatographic techniques can be used in the specific diagnosis.

  3. Tannin, oxalate, saponin, cyanogenic and cardiac glycosides ...

    African Journals Online (AJOL)

    Two species of cola, Cola nitida and Cola acuminate, were investigated for their possible relative contents of the secondary plant products:- tannin, oxalate, saponin, cyanogenic and cardiac glycosides. The two cola species gave low levels of tannin and oxalate but very high levels of cyanogenic and cardiac glycosides as ...

  4. Two New Triterpene Glycosides from Centella asiatica

    Science.gov (United States)

    Phytochemical investigation of the leaves of Centella asiatica resulted in the isolation and characterization of one new ursane type triterpene glycoside; asiaticoside G along with nine known compounds, that were characterized as ursane type triterpenes and /or their glycoside; asiatic acid (2), mad...

  5. Steroidal glycosides from the starfish Gomophia watsoni

    OpenAIRE

    Riccio, R; D'Auria, M.V.; Iorizzi, M.; Minale, L.; Laurent, Dominique; Duhet, Daniel

    1985-01-01

    Two novel steroidal glycosides have been isolated from the starfish Gomophia watsoni; they co-occur with one known glycoside and two new polyhydroxysteroids. The structures of the new metabolites, 2,3,4 and 5, were determined on the basis of spectral data. (Résumé d'auteur)

  6. Megastigmane glycosides from Urena lobata.

    Science.gov (United States)

    Su, Cong; Qi, Bowen; Wang, Juan; Ding, Ning; Wu, Yun; Shi, Xiao-Ping; Zhu, Zhi-Xiang; Liu, Xiao; Wang, Xiao-Hui; Zheng, Jiao; Tu, Peng-Fei; Shi, She-Po

    2018-02-12

    Five new megastigmane glycosides, urenalobasides A-E (1-5), together with 11 known ones (6-16) were isolated from Urena lobata. Their structures were determined by extensive spectroscopic and spectrometric data (1D and 2D NMR, IR, and HRESIMS) and calculated electronic circular dichroism method. Compounds 1 and 2 are two unusual megastigmanes structurally containing a 6/5 fused ring system. Compound 3 exhibits inhibition of nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with IC 50 value of 53.7 ± 1.0 μM (positive control, dexamethasone, IC 50  = 16.6 ± 0.8 μM). Copyright © 2018 Elsevier B.V. All rights reserved.

  7. Four new phenolic glycosides from Baoyuan decoction

    Directory of Open Access Journals (Sweden)

    Xiaoli Ma

    2017-03-01

    Full Text Available Four new phenolic glycosides, including two flavonoid glycosides (1 and 2 and two lignan glycosides (3 and 4, were isolated from the traditional Chinese medicine formula, Baoyuan decoction. Their structures were established by detailed analysis of the NMR and HR-ESI-MS spectroscopic data and their absolute configurations were determined by the experimental electronic circular dichroism data as well as chemical methods. Furthermore, the sources of the four new compounds were determined by the UPLC-Qtrap-MS method, which proved that 1 and 2 are originated from Glycyrrhiza uralensis, and 3 and 4 are from Cinnamomum cassia.

  8. Influence of nonionic branched-chain alkyl glycosides on a model nano-emulsion for drug delivery systems.

    Science.gov (United States)

    Ahmad, Noraini; Ramsch, Roland; Llinàs, Meritxell; Solans, Conxita; Hashim, Rauzah; Tajuddin, Hairul Anuar

    2014-03-01

    The effect of incorporating new nonionic glycolipid surfactants on the properties of a model water/nonionic surfactant/oil nano-emulsion system was investigated using branched-chain alkyl glycosides: 2-hexyldecyl-β(/α)-D-glucoside (2-HDG) and 2-hexyldecyl-β(/α)-D-maltoside (2-HDM), whose structures are closely related to glycero-glycolipids. Both 2-HDG and 2-HDM have an identical hydrophobic chain (C16), but the former consists a monosaccharide glucose head group, in contrast to the latter which has a disaccharide maltose unit. Consequently, their hydrophilic-lipophilic balance (HLB) is different. The results obtained have shown that these branched-chain alkyl glycosides affect differently the stability of the nano-emulsions. Compared to the model nano-emulsion, the presence of 2-HDG reduces the oil droplet size, whereas 2-HDM modify the properties of the model nano-emulsion system in terms of its droplet size and storage time stability at high temperature. These nano-emulsions have been proven capable of encapsulating ketoprofen, showing a fast release of almost 100% in 24h. Thus, both synthetically prepared branched-chain alkyl glycosides with mono- and disaccharide sugar head groups are suitable as nano-emulsion stabilizing agents and as drug delivery systems in the future. Copyright © 2013 Elsevier B.V. All rights reserved.

  9. A new steroidal glycoside and a new phenyl glycoside from a ripe cherry tomato.

    Science.gov (United States)

    Ono, Masateru; Shiono, Yuki; Yanai, Yoshihiro; Fujiwara, Yukio; Ikeda, Tsuyoshi; Nohara, Toshihiro

    2008-10-01

    A new steroidal glycoside and a new phenyl glycoside have been isolated from a ripe cherry tomato [Lycopersicon esculentum var. cerasiforme (DUNAL) ALEF., Solanaceae] along with two known steroidal alkaloid glycosides, esculeoisides A and B, and five aromatic compounds, zizibeoside I, benzyl alcohol beta-gentiobioside, rutin, methyl caffeate, and phenylalanine. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.

  10. Monosaccharide-responsive phenylboronate-polyol cell scaffolds for cell sheet and tissue engineering applications.

    Directory of Open Access Journals (Sweden)

    Rachamalla Maheedhar Reddy

    Full Text Available Analyte-responsive smart polymeric materials are of great interest and have been actively investigated in the field of regenerative medicine. Phenylboronate containing copolymers form gels with polyols under alkaline conditions. Monosaccharides, by virtue of their higher affinity towards boronate, can displace polyols and solubilize such gels. In the present study, we investigate the possibility of utilizing phenylboronate-polyol interactions at physiological pH in order to develop monosaccharide-responsive degradable scaffold materials for systems dealing with cells and tissues. Amine assisted phenylboronate-polyol interactions were employed to develop novel hydrogel and cryogel scaffolds at neutral pH. The scaffolds displayed monosaccharide inducible gel-sol phase transformability. In vitro cell culture studies demonstrated the ability of scaffolds to support cell adhesion, viability and proliferation. Fructose induced gel degradation is used to recover cells cultured on the hydrogels. The cryogels displayed open macroporous structure and superior mechanical properties. These novel phase transformable phenylboronate-polyol based scaffolds displayed a great potential for various cell sheet and tissue engineering applications. Their monosaccharide responsiveness at physiological pH is very useful and can be utilized in the fields of cell immobilization, spheroid culture, saccharide recognition and analyte-responsive drug delivery.

  11. Glycosaminoglycan Monosaccharide Blocks Analysis by Quantum Mechanics, Molecular Dynamics, and Nuclear Magnetic Resonance

    Directory of Open Access Journals (Sweden)

    Sergey A. Samsonov

    2014-01-01

    Full Text Available Glycosaminoglycans (GAGs play an important role in many biological processes in the extracellular matrix. In a theoretical approach, structures of monosaccharide building blocks of natural GAGs and their sulfated derivatives were optimized by a B3LYP6311ppdd//B3LYP/6-31+G(d method. The dependence of the observed conformational properties on the applied methodology is described. NMR chemical shifts and proton-proton spin-spin coupling constants were calculated using the GIAO approach and analyzed in terms of the method's accuracy and sensitivity towards the influence of sulfation, O1-methylation, conformations of sugar ring, and ω dihedral angle. The net sulfation of the monosaccharides was found to be correlated with the 1H chemical shifts in the methyl group of the N-acetylated saccharides both theoretically and experimentally. The ω dihedral angle conformation populations of free monosaccharides and monosaccharide blocks within polymeric GAG molecules were calculated by a molecular dynamics approach using the GLYCAM06 force field and compared with the available NMR and quantum mechanical data. Qualitative trends for the impact of sulfation and ring conformation on the chemical shifts and proton-proton spin-spin coupling constants were obtained and discussed in terms of the potential and limitations of the computational methodology used to be complementary to NMR experiments and to assist in experimental data assignment.

  12. Comparative decomposition kinetics of neutral monosaccharides by microwave and induction heating treatments.

    Science.gov (United States)

    Tsubaki, Shuntaro; Oono, Kiriyo; Onda, Ayumu; Yanagisawa, Kazumichi; Azuma, Jun-ichi

    2013-06-28

    The stabilities of five neutral monosaccharides (glucose, galactose, mannose, arabinose, and xylose) were kinetically compared after the molecules were submitted to microwave heating (internal heating) and induction heating (external heating) under completely identical thermal histories by employing PID (proportional, integral, and derivative) temperature controlled ovens and homogeneous mixing. By heating in water at 200°C, the rate constants for the decomposition reactions varied from 2.13×10(-4) to 3.87×10(-4)s(-1) for microwave heating; however, the values increased by 1.1- to 1.5-fold for induction heating. Similarly, in a dilute (0.8%) sulfuric acid solution, the decomposition rate constants varied from 0.61×10(-3) to 2.00×10(-3)s(-1) for microwave heating; however, the values increased by 1.5- to 2.2-fold for induction heating. The results show that microwave heating imparts greater stability to neutral monosaccharides than does induction heating. The undesirable decomposition of monosaccharides at the surface boundary of reactor walls may have increased the probability of monosaccharide decomposition during induction heating. Copyright © 2013 Elsevier Ltd. All rights reserved.

  13. A caffeoyl phenylethanoid glycoside from Plantago myosuros

    DEFF Research Database (Denmark)

    Franzyk, Henrik; Husum, Tommy Lykke; Jensen, Søren Rosendal

    1998-01-01

    From Plantago myosuros, the iridoid glucoside, aucubin was isolated, together with the caffeoyl phenylethanoid glycosides, plantalloside and verbascoside. Plantalloside is a new verbascoside analogue with a beta-allopyranosyl moiety. The structure was elucidated by NMR spectroscopy. (C) 1998 Else...

  14. Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides.

    Science.gov (United States)

    Dembitsky, Valery M

    2005-03-01

    Polyether glycosidic ionophores and macrocyclic glycosides are of great interest, especially for the medicinal and pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antibiotics, anticancer agents, or in industry. More than 300 interesting and unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

  15. Diterpene glycosides from Stevia phlebophylla A. Gray.

    Science.gov (United States)

    Ceunen, Stijn; Wim, De Borggraeve; Compernolle, Frans; Mai, Anh Hung; Geuns, Jan M C

    2013-09-20

    The rare Mexican species Stevia phlebophylla A. Gray was long considered to be the only known Stevia species, beside the well-known S. rebaudiana, containing the highly sweet diterpenoid steviol glycosides. We report a re-evaluation of this claim after phytochemically screening leaves obtained from two herbarium specimens of S. phlebophylla for the presence of steviol glycosides. Despite extensive MS analyses, no steviol glycosides could be unambiguously verified. Instead, the main chromatographic peak eluting at retention times similar to those of steviol glycosides was identified as a new compound, namely 16β-hydroxy-17-acetoxy-ent-kauran-19-oic acid-(6-O-β-D-xylopyranosyl-β-D-glucopyranosyl) ester (1) on the basis of extensive NMR and MS data as well as the characterization of its acid hydrolysate. Seven more compounds were detected by ESIMS which are possibly structurally related to 1. It can therefore be concluded that S. phlebophylla is unlikely to contain significant amounts of steviol glycosides, if any. Copyright © 2013 Elsevier Ltd. All rights reserved.

  16. A new lignan glycoside from Forsythia suspensa.

    Science.gov (United States)

    Li, Chang; Dai, Yi; Duan, Ying-Hui; Liu, Ming-Li; Yao, Xin-Sheng

    2014-09-01

    Phytochemical investigation on Forsythia suspensa (Thunb.) Vahl afforded ten compounds, including five lignan glycosides and five phenylethanoid glycosides. The compounds were isolated by using HP-20 macroporous resin, silica gel, octadecyl silica gel (ODS), size exclusion chromatography resin HW-40 chromatography, and preparative HPLC. The structures were established through application of extensive spectroscopic methods, including ESI-MS, 1D-and 2D-NMR spectroscopy. They were identified as forsythialanside E (1), 8'-hydroxypinoresinol-4'-O-β-D-glucoside (2), 8'-hydroxypinoresinol (3), lariciresinol-4'-O-β-D-glucoside (4), lariciresinol-4-O-β-D-glucoside (5), forsythoside H (6), forsythoside I (7), forsythoside F (8), plantainoside B (9), and plantainoside A (10). Compound 1 was a new lignan glycoside. Copyright © 2014 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

  17. [Study on Monosaccharide Compositions of Polysaccharide in Dendrobium Stems of Different Resources by PMP-HPCE].

    Science.gov (United States)

    Chen, Nai-dong; Meng, Yun-fei; Yao, Hou-jun; Cao, Cai-yun; Chen, Chen; Li, Jun

    2015-08-01

    To establish a PMP-HPCE method for comparing the monosaccharides of polysaccharide in tissue-cultured and wild Dedrobium huoshanese and Dedrobium moniliforme as well as wild Dedrobium henanese, in order to investigate the similarities of their bioactive components. The PMP-monosaccharides of polysaccharide from the five investigated Dedrobium samples were separated by HPCE on a fused silica capillary column(100 cm x 50 µm) at 25 °C with 350 mmol/L BAS (adjusted to pH 10 with 1.0 mol/L NaOH) as running buffer for 34 min. The applied voltage was 20 kV and the detection wavelength was set at 250 nm. Total six monosaccharides including xylose, glucose, mannose, galactose, galacturonic acid and ribose were detected in the five Dendrobiurms samples and the similarity coefficients between the ten batches of the same Dendrobium species were all above 0. 98,while remarkable dissimilarity were exhibited among species and different resources. PMP-HPCE technique combined with chemometrics is simple, convenient, precise, reproducible and proved to be an effective strategy for identifying the species and origins, especially in the quality assessment of Dendrobium stems.

  18. Ammoxidation of lignocellulosic materials: formation of nonheterocyclic nitrogenous compounds from monosaccharides.

    Science.gov (United States)

    Klinger, Karl Michael; Liebner, Falk; Hosoya, Takashi; Potthast, Antje; Rosenau, Thomas

    2013-09-25

    Ammoxidized technical lignins are valuable soil-improving materials that share many similarities with native terrestrial humic substances. In contrast to lignins, the chemical fate of carbohydrates as typical minor constituents of technical lignins during the ammoxidation processes has not been thoroughly investigated. Recently, we reported the formation of N-heterocyclic, ecotoxic compounds (OECD test 201) from both monosaccharides (D-glucose, D-xylose) and polysaccharides (cellulose, xylan) under ammoxidation conditions and showed that monosaccharides are a source more critical than polysaccharides in this respect. GC/MS-derivatization analysis of the crude product mixtures revealed that ammoxidation of carbohydrates which resembles the conditions encountered in nonenzymatical browning of foodstuff affords also a multitude of nonheterocyclic nitrogenous compounds such as aminosugars, glycosylamines, ammonium salts of aldonic, deoxyaldonic, oxalic and carbaminic acids, urea, acetamide, α-hydroxyamides, and even minor amounts of α-amino acids. D-glucose and D-xylose afforded largely similar product patterns which differed from each other only for those products that were formed under preservation of the chain integrity and stereoconfiguration of the respective monosaccharide. The kinetics and reaction pathways involved in the formation of the different classes of nitrogenous compounds under ammoxidation conditions are discussed.

  19. Na/sup +/-independent, phloretin-sensitive monosaccharide transport system in isolated intestinal epithelial cells. [Chickens

    Energy Technology Data Exchange (ETDEWEB)

    Kimmich, G.A.; Randles, J.

    1975-01-01

    A monosaccharide transport system in addition to the active Na/sup +/-dependent system characteristic of the brush border surface of vertebrate intestinal tissue has been identified in isolated chick intestinal epithelial cells. The newly described system differs in several characteristics from the Na/sup +/-dependent process, including function in the absence of Na/sup +/; a high sensitivity to phloretin, relative insensitivity to phlorizin; different substrate specificity; and a very high K/sub T/ and V/sub max/. The system apparently functions only in a facilitated diffusion manner so that it serves to move monosaccharide across the cell membrane down its chemical gradient. An appreciable fraction of total sugar efflux occurs via the Na/sup +/-independent carrier from cells which have accumulated sugar to a steady state. Phloretin selectively blocks this efflux so that a normal steady-state sugar gradient of seven- to eightfold is transformed to a new steady-state gradient which is greater than 14-fold. Locus of the new system is tentatively ascribed to the serosal cell surface where it would serve for monosaccharide transfer between enterocyte and lamina propria of the villus. (auth)

  20. Techno-economic analysis of monosaccharide production via fast pyrolysis of lignocellulose.

    Science.gov (United States)

    Zhang, Yanan; Brown, Tristan R; Hu, Guiping; Brown, Robert C

    2013-01-01

    The economic feasibility of a facility producing monosaccharides, hydrogen and transportation fuels via fast pyrolysis and upgrading pathway was evaluated by modeling a 2000 dry metric ton biomass/day facility using Aspen Plus®. Equipment sizing and cost were based on Aspen Economic Evaluation® software. The results indicate that monosaccharide production capacity could reach 338 metric tons/day. Co-product yields of hydrogen and gasoline were 23.4 and 141 metric tons/day, respectively. The total installed equipment and total capital costs were estimated to be $210 million and $326 million, respectively. A facility internal rate of return (IRR) of 11.4% based on market prices of $3.33/kg hydrogen, $2.92/gal gasoline and diesel, $0.64/kg monosaccharide was calculated. Sensitivity analysis demonstrates that fixed capital cost, feedstock cost, product yields, and product credits have the greatest impacts on facility IRR. Further research is needed to optimize yield of sugar via the proposed process to improve economic feasibility. Copyright © 2012 Elsevier Ltd. All rights reserved.

  1. The role of Monosaccharide Transport Proteins in carbohydrate assimilation, distribution, metabolism and homeostasis

    Science.gov (United States)

    Cura, Anthony J.; Carruthers, Anthony

    2012-01-01

    The facilitated diffusion of glucose, galactose, fructose, urate, myoinositol and dehydroascorbic acid in mammals is catalyzed by a family of 14 monosaccharide transport proteins called GLUTs. These transporters may be divided into 3 classes according to sequence similarity and function/substrate specificity. GLUT1 appears to be highly expressed in glycolytically active cells and has been co-opted in vitamin C auxotrophs to maintain the redox state of the blood through transport of dehydroascorbate. Several GLUTs are definitive glucose/galactose transporters, GLUT2 and GLUT5 are physiologically important fructose transporters, GLUT9 appears to be a urate transporter while GLUT13 (HMIT1) is a proton/myoinositol co-transporter. The physiologic substrates of some GLUTs remain to be established. The GLUTs are expressed in a tissue specific manner where affinity, specificity and capacity for substrate transport are paramount for tissue function. Although great strides have been made in characterizing GLUT-catalyzed monosaccharide transport and mapping GLUT membrane topography and determinants of substrate specificity, a unifying model for GLUT structure and function remains elusive. The GLUTs play a major role in carbohydrate homeostasis and the redistribution of sugar-derived carbons among the various organ systems. This is accomplished through a multiplicity of GLUT-dependent glucose sensing and effector mechanisms that regulate monosaccharide ingestion, absorption, distribution, cellular transport and metabolism and recovery/retention. Glucose transport and metabolism have co-evolved in mammals to support cerebral glucose utilization. PMID:22943001

  2. [Phenylethanoid glycosides from root of Picrorhiza scrophulariiflora].

    Science.gov (United States)

    Wang, Hao; Ye, Wen-Cai; Xiong, Fei; Zhao, Shou-Xun

    2004-06-01

    To study the phenylethanoid glycosides from root of Picrorhiza scrophulariiflora. Column chromatographic techniques were used for isolation and purification of chemical constituents of the plant and the structures were identified by spectroscopic analysis. Six phenylethanoid glycosides were isolated and elucidated as: 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside (1), 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-beta-D-glucopyranosyl (1-->3) beta-D-glucopyranoside (2), scroside B (3), hemiphroside A (4), plantainoside D (5) and scroside A (6), respectively. Compounds 1, 2, 4 and 5 were isolated from this plant for the first time and compound 2 was firstly obtained from natural source.

  3. A New Diterpene Glycoside from Stevia rebaudiana

    Directory of Open Access Journals (Sweden)

    Indra Prakash

    2011-04-01

    Full Text Available From the commercial extract of the leaves of Stevia rebaudiana, a new diterpene glycoside was isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compound was identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy] ent-kaur-16-en-19-oic acid-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl ester (1 on the basis of extensive spectroscopic (NMR and MS and chemical studies.

  4. A new diterpene glycoside from Stevia rebaudiana.

    Science.gov (United States)

    Chaturvedula, Venkata Sai Prakash; Prakash, Indra

    2011-04-04

    From the commercial extract of the leaves of Stevia rebaudiana, a new diterpene glycoside was isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compound was identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl) ester (1) on the basis of extensive spectroscopic (NMR and MS) and chemical studies.

  5. A New Diterpene Glycoside from Stevia rebaudiana

    OpenAIRE

    Indra Prakash; Venkata Sai Prakash Chaturvedula

    2011-01-01

    From the commercial extract of the leaves of Stevia rebaudiana, a new diterpene glycoside was isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compound was identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl) ester (1) on the basis of extensive spectroscopic (NMR and MS) and chemical studies.

  6. Veronica: Acylated flavone glycosides as chemosystematic markers

    DEFF Research Database (Denmark)

    Albach, Dirk C.; Grayer, Renée J.; Kite, Geoffrey C.

    2005-01-01

    HPLC/DAD and LCeMS of an extract of Veronica spicata subgenus Pseudolysimachium, Plantaginaceae) revealed the presence of six 6-hydroxyluteolin glycosides acylated with phenolic acids, three of which are new compounds and which we called spicosides. A flavonoid survey of seven more species...... instead. Spicosides appeared to be common in subgenus Pseudolysimachium (detected in five out of eight species), but we did not find them in subgenus Pentasepalae. Previously, acetylated 8-hydroxyflavone glycosides have been isolated from or detected in eight species of V. subgenus Pentasepalae (in 13...

  7. Combining multivariate analysis and monosaccharide composition modeling to identify plant cell wall variations by Fourier Transform Near Infrared spectroscopy

    Directory of Open Access Journals (Sweden)

    Smith-Moritz Andreia M

    2011-08-01

    Full Text Available Abstract We outline a high throughput procedure that improves outlier detection in cell wall screens using FT-NIR spectroscopy of plant leaves. The improvement relies on generating a calibration set from a subset of a mutant population by taking advantage of the Mahalanobis distance outlier scheme to construct a monosaccharide range predictive model using PLS regression. This model was then used to identify specific monosaccharide outliers from the mutant population.

  8. A new phenolic glycoside from the barks of Cinnamomum cassia

    National Research Council Canada - National Science Library

    Zeng, Junfen; Xue, Yongbo; Lai, Yongji; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui; Zhang, Jinwen

    2014-01-01

    A new phenolic glycoside (1), named methyl 2-phenylpropanoate-2-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside, was isolated from the barks of Cinnamomum cassia, along with three known phenolic glycosides and four known lignan glycosides...

  9. Novel efficient routes to indoxyl glycosides for monitoring glycosidase activities.

    Science.gov (United States)

    Böttcher, Stephan; Hederos, Markus; Champion, Elise; Dékány, Gyula; Thiem, Joachim

    2013-07-19

    A new efficient synthesis for broad access to indoxyl glycosides was developed. Indoxylic acid allyl ester linked to a sugar structure served as the key intermediate in this route. Selective ester cleavage and mild decarboxylation led to the corresponding indoxyl glycosides in good yields. This synthesis was applied for preparation of indoxyl glycosides of fucose, sialic acid, and 6'-sialyl lactose.

  10. Perspectives for the Industrial Enzymatic Production of Glycosides

    NARCIS (Netherlands)

    Roode, de B.M.; Franssen, M.C.R.; Padt, van der A.; Boom, R.M.

    2003-01-01

    Glycosides are of commercial interest for industry in general and specifically for the pharmaceutical and food industry. Currently chemical preparation of glycosides will not meet EC food regulations, and therefore chemical preparation of glycosides is not applicable in the food industry. Thus,

  11. cultured cells under phenylethanoid glycosides (PEG) 6000

    African Journals Online (AJOL)

    akpobome

    2013-03-13

    Mar 13, 2013 ... This study was carried out to investigate the effect of the intracellular signaling molecule nitric oxide. (NO) on osmoregulation of tobacco cells under osmotic stress caused by phenylethanoid glycosides. 6000 (PEG 6000). The results ... is one of the major environmental factors limiting plant productivity and ...

  12. Anticancer Activity of Sea Cucumber Triterpene Glycosides

    Science.gov (United States)

    Aminin, Dmitry L.; Menchinskaya, Ekaterina S.; Pisliagin, Evgeny A.; Silchenko, Alexandra S.; Avilov, Sergey A.; Kalinin, Vladimir I.

    2015-01-01

    Triterpene glycosides are characteristic secondary metabolites of sea cucumbers (Holothurioidea, Echinodermata). They have hemolytic, cytotoxic, antifungal, and other biological activities caused by membranotropic action. These natural products suppress the proliferation of various human tumor cell lines in vitro and, more importantly, intraperitoneal administration in rodents of solutions of some sea cucumber triterpene glycosides significantly reduces both tumor burden and metastasis. The anticancer molecular mechanisms include the induction of tumor cell apoptosis through the activation of intracellular caspase cell death pathways, arrest of the cell cycle at S or G2/M phases, influence on nuclear factors, NF-κB, and up-down regulation of certain cellular receptors and enzymes participating in cancerogenesis, such as EGFR (epidermal growth factor receptor), Akt (protein kinase B), ERK (extracellular signal-regulated kinases), FAK (focal adhesion kinase), MMP-9 (matrix metalloproteinase-9) and others. Administration of some glycosides leads to a reduction of cancer cell adhesion, suppression of cell migration and tube formation in those cells, suppression of angiogenesis, inhibition of cell proliferation, colony formation and tumor invasion. As a result, marked growth inhibition of tumors occurs in vitro and in vivo. Some holothurian triterpene glycosides have the potential to be used as P-gp mediated MDR reversal agents in combined therapy with standard cytostatics. PMID:25756523

  13. Flavone C-glycosides from Anthurium andraeanum.

    Science.gov (United States)

    Clark, Benjamin R; Suzuki, Jon Y; Bliss, Barbara J; Borris, Robert P

    2012-06-01

    We describe here the isolation of three flavone 6-C-glycosides from the leaves of Anthurium andraeanum, The two new flavones were identified through detailed spectroscopic analysis as 4"'-(3,4-dimethoxycinnamoyl)-embinin (2) and 4"'-ferruloyl-embinin (3).

  14. Glycoside hydrolases having multiple hydrolase activities

    Energy Technology Data Exchange (ETDEWEB)

    Chen, Zhiwei; Friedland, Gregory D.; Chhabra, Swapnil R.; Chivian, Dylan C.; Simmons, Blake A

    2017-08-08

    Glycoside hydrolases having at least two different hydrolytic activities are provided. In one embodiment, an isolated recombinant hydrolase having at least two activities selected from a group including asparagine derivatives, glutamine derivatives, and histidine derivatives is provided. Further, a method of generating free sugars from a mixture comprising asparagine derivatives, glutamine derivatives, and histidine derivatives is provided.

  15. Characterization and engineering of thermostable glycoside hydrolases

    NARCIS (Netherlands)

    Lieshout, van J.F.T.

    2007-01-01

    Glycosidehydrolasesform a class of enzymes that play an important role in sugar-converting processes. They are applied as biocatalyst in both the hydrolysis of natural polymers to mono- andoligo-saccharides, and the reverse hydrolysis or

  16. Anticancer Activity of Sea Cucumber Triterpene Glycosides

    Directory of Open Access Journals (Sweden)

    Dmitry L. Aminin

    2015-03-01

    Full Text Available Triterpene glycosides are characteristic secondary metabolites of sea cucumbers (Holothurioidea, Echinodermata. They have hemolytic, cytotoxic, antifungal, and other biological activities caused by membranotropic action. These natural products suppress the proliferation of various human tumor cell lines in vitro and, more importantly, intraperitoneal administration in rodents of solutions of some sea cucumber triterpene glycosides significantly reduces both tumor burden and metastasis. The anticancer molecular mechanisms include the induction of tumor cell apoptosis through the activation of intracellular caspase cell death pathways, arrest of the cell cycle at S or G2/M phases, influence on nuclear factors, NF-κB, and up-down regulation of certain cellular receptors and enzymes participating in cancerogenesis, such as EGFR (epidermal growth factor receptor, Akt (protein kinase B, ERK (extracellular signal-regulated kinases, FAK (focal adhesion kinase, MMP-9 (matrix metalloproteinase-9 and others. Administration of some glycosides leads to a reduction of cancer cell adhesion, suppression of cell migration and tube formation in those cells, suppression of angiogenesis, inhibition of cell proliferation, colony formation and tumor invasion. As a result, marked growth inhibition of tumors occurs in vitro and in vivo. Some holothurian triterpene glycosides have the potential to be used as P-gp mediated MDR reversal agents in combined therapy with standard cytostatics.

  17. Methods for the enzymatic modification of steviol glycosides, modified steviol glycosides obtainable thereby, and the use thereof as sweeteners

    NARCIS (Netherlands)

    te Poele, Evelien; Dijkhuizen, Lubbert; Gerwig, Gerrit; Kamerling, Johannis

    2016-01-01

    The present invention relates generally to the production of steviol glycosides. Provided is a method for enzymatically providing a modified steviol glycoside, comprising incubating a steviol glycoside substrate in the presence of sucrose and the glucansucrase GTF180 of Lactobacillus reuteri strain

  18. Advance on the Flavonoid C-glycosides and Health Benefits.

    Science.gov (United States)

    Xiao, Jianbo; Capanoglu, Esra; Jassbi, Amir Reza; Miron, Anca

    2016-07-29

    The dietary flavonoids, especially their glycosides, are the most vital phytochemicals in diets and are of great general interest due to their diverse bioactivity. Almost all natural flavonoids exist as their O-glycoside or C-glycoside forms in plants. The dietary flavonoid C-glycosides have received less attention than their corresponding O-glycosides. This review summarizes current knowledge regarding flavonoid C-glycosides and their influence on human health. Among the flavonoid C-glycosides, flavone C-glycosides, especially vitexin, isoorientin, orientin, isovitexin and their multiglycosides are more frequently mentioned than others. Flavonoid C-monoglycosides are poorly absorbed in human beings with very few metabolites in urine and blood and are deglycosylated and degraded by human intestinal bacteria in colon. However, flavonoid C-multiglycosides are absorbed unchanged in the intestine and distributed to other tissues. Flavonoid C-glycosides showed significant antioxidant activity, anticancer and antitumor activity, hepatoprotective activity, anti-inflammatory activity, anti-diabetes activity, antiviral activity, antibacterial and antifungal activity, and other biological effects. It looks like that the C-glycosylflavonoids in most cases showed higher antioxidant and anti-diabetes potential than their corresponding O-glycosylflavonoids and aglycones. However, there is a lack of in vivo data on the biological benefits of flavonoid C-glycosides. It is necessary to investigate more on how flavonoid C-glycosides prevent and handle the diseases.

  19. Dual Roles of O-Glucose Glycans Redundant with Monosaccharide O-Fucose on Notch in Notch Trafficking.

    Science.gov (United States)

    Matsumoto, Kenjiroo; Ayukawa, Tomonori; Ishio, Akira; Sasamura, Takeshi; Yamakawa, Tomoko; Matsuno, Kenji

    2016-06-24

    Notch is a transmembrane receptor that mediates cell-cell interactions and controls various cell-fate specifications in metazoans. The extracellular domain of Notch contains multiple epidermal growth factor (EGF)-like repeats. At least five different glycans are found in distinct sites within these EGF-like repeats. The function of these individual glycans in Notch signaling has been investigated, primarily by disrupting their individual glycosyltransferases. However, we are just beginning to understand the potential functional interactions between these glycans. Monosaccharide O-fucose and O-glucose trisaccharide (O-glucose-xylose-xylose) are added to many of the Notch EGF-like repeats. In Drosophila, Shams adds a xylose specifically to the monosaccharide O-glucose. We found that loss of the terminal dixylose of O-glucose-linked saccharides had little effect on Notch signaling. However, our analyses of double mutants of shams and other genes required for glycan modifications revealed that both the monosaccharide O-glucose and the terminal dixylose of O-glucose-linked saccharides function redundantly with the monosaccharide O-fucose in Notch activation and trafficking. The terminal dixylose of O-glucose-linked saccharides and the monosaccharide O-glucose were required in distinct Notch trafficking processes: Notch transport from the apical plasma membrane to adherens junctions, and Notch export from the endoplasmic reticulum, respectively. Therefore, the monosaccharide O-glucose and terminal dixylose of O-glucose-linked saccharides have distinct activities in Notch trafficking, although a loss of these activities is compensated for by the presence of monosaccharide O-fucose. Given that various glycans attached to a protein motif may have redundant functions, our results suggest that these potential redundancies may lead to a serious underestimation of glycan functions. © 2016 by The American Society for Biochemistry and Molecular Biology, Inc.

  20. Dual Roles of O-Glucose Glycans Redundant with Monosaccharide O-Fucose on Notch in Notch Trafficking*

    Science.gov (United States)

    Matsumoto, Kenjiroo; Ayukawa, Tomonori; Ishio, Akira; Sasamura, Takeshi; Yamakawa, Tomoko; Matsuno, Kenji

    2016-01-01

    Notch is a transmembrane receptor that mediates cell-cell interactions and controls various cell-fate specifications in metazoans. The extracellular domain of Notch contains multiple epidermal growth factor (EGF)-like repeats. At least five different glycans are found in distinct sites within these EGF-like repeats. The function of these individual glycans in Notch signaling has been investigated, primarily by disrupting their individual glycosyltransferases. However, we are just beginning to understand the potential functional interactions between these glycans. Monosaccharide O-fucose and O-glucose trisaccharide (O-glucose-xylose-xylose) are added to many of the Notch EGF-like repeats. In Drosophila, Shams adds a xylose specifically to the monosaccharide O-glucose. We found that loss of the terminal dixylose of O-glucose-linked saccharides had little effect on Notch signaling. However, our analyses of double mutants of shams and other genes required for glycan modifications revealed that both the monosaccharide O-glucose and the terminal dixylose of O-glucose-linked saccharides function redundantly with the monosaccharide O-fucose in Notch activation and trafficking. The terminal dixylose of O-glucose-linked saccharides and the monosaccharide O-glucose were required in distinct Notch trafficking processes: Notch transport from the apical plasma membrane to adherens junctions, and Notch export from the endoplasmic reticulum, respectively. Therefore, the monosaccharide O-glucose and terminal dixylose of O-glucose-linked saccharides have distinct activities in Notch trafficking, although a loss of these activities is compensated for by the presence of monosaccharide O-fucose. Given that various glycans attached to a protein motif may have redundant functions, our results suggest that these potential redundancies may lead to a serious underestimation of glycan functions. PMID:27129198

  1. Monosaccharide composition of Herniaria glabra L. and Herniaria polygama J.Gay

    Directory of Open Access Journals (Sweden)

    Kozachok Solomiia

    2016-09-01

    Full Text Available The plants from Herniaria genus (Caryophyllaceae family are mainly applied as diuretic agents for the treatment of kidney and gall-stones, gouts, urinary tract infections, hypertension and diabetes. The most widely spread species in Europe is Herniaria glabra L. (HG. Herniaria polygama J.Gay (HP is found growing from Eastern Europe to Asia. Surprisingly, no work has been reported on the analysis of primary metabolites of HP yet and there is only a limited data on HG. The aim of our study was to establish the monosaccharide composition after a complete hydrolysis and in a free state in the entire herbs of HG and HP harvested in the western and central parts of Ukraine. The carbohydrates were separated by gas chromatography-mass spectrometry after conversion into volatile derivatives as aldononitrile acetate. As a result, the monosaccharide composition after a total hydrolysis was established with the contribution of the following components: D-rhamnose, D-arabinose, D-fucose, D-xylose, D-manose, D-glucose, D-galactose, D-pinitol, myo-inisitol, D-mannitol, D-dulcitol. In a free state it was detected: D-fructose, D-glucose, D-galactose, D-pinitol, myo-inisitol, D-mannitol and D-saccharose. The following monosaccharides were found in the most abundant quantities in HG and HP respectively: glucose was determined as the major component – 33.40 and 22.80 mg/g, the second dominant sugar was pinitol – 16.80 and 18.07 mg/g, followed by galactose – 13.88 mg/g in HG and arabinose – 8.13 mg/g in HP. Sugars were determined in these plant species for the first time and this finding shed new light on their pharmacological application.

  2. Design, synthesis and biological evaluation of fucose-truncated monosaccharide analogues of ipomoeassin F.

    Science.gov (United States)

    Zong, Guanghui; Hirsch, Melissa; Mondrik, Collin; Hu, Zhijian; Shi, Wei Q

    2017-06-15

    Ipomoeassin F is a plant-derived macrocyclic glycolipid with single-digit nanomolar IC50 values against cancer cell growth. In previous structure-activity relationship studies, we have demonstrated that certain modifications around the fucoside moiety did not cause significant cytotoxicity loss. To further elucidate the effect of the fucoside moiety on the biological activity, we describe here the design and synthesis of several fucose-truncated monosaccharide analogues of ipomoeassin F. Subsequent biological evaluation strongly suggests that the 6-membered ring of the fucoside moiety is essential to the overall conformation of the molecule, thereby influencing bioactivity. Copyright © 2017 Elsevier Ltd. All rights reserved.

  3. The distribution of monosaccharides and hexosamines in the oviduct of Salamandra salamandra (L.) (Amphibia, Urodela).

    Science.gov (United States)

    Greven, H; Baldus, B B

    1984-01-01

    Biochemical analysis of the different segments of the oviduct in the ovoviviparous salamander, Salamandra salamandra, reveals the monosaccharides glucose, galactose, fucose, mannose, ribose and the hexosamines glucosamine and mannosamine. In segment 1 (pars recta) ribose and mannose are absent, and in segments 2 (p. convoluta I) and 5 (p. convoluta IV, uterus) mannose is not detectable; fucose is absent in the uterus. Segments 3 (p. convoluta II) and 4 (p. convoluta II) contain all sugars identified. The main hexoses present in the glandular segments are galactose, fucose and glucose.

  4. Microwave assisted extraction-solid phase extraction for high-efficient and rapid analysis of monosaccharides in plants.

    Science.gov (United States)

    Zhang, Ying; Li, Hai-Fang; Ma, Yuan; Jin, Yan; Kong, Guanghui; Lin, Jin-Ming

    2014-11-01

    Monosaccharides are the fundamental composition units of saccharides which are a common source of energy for metabolism. An effective and simple method consisting of microwave assisted extraction (MAE), solid phase extraction (SPE) and high performance liquid chromatography-refractive index detector (HPLC-RID) was developed for rapid detection of monosaccharides in plants. The MAE was applied to break down the structure of the plant cells and release the monosaccharides, while the SPE procedure was adopted to purify the extract before analysis. Finally, the HPLC-RID was employed to separate and analyze the monosaccharides with amino column. As a result, the extraction time was reduced to 17 min, which was nearly 85 times faster than soxhlet extraction. The recoveries of arabinose, xylose, fructose and glucose were 85.01%, 87.79%, 103.17%, and 101.24%, with excellent relative standard deviations (RSDs) of 1.94%, 1.13%, 0.60% and 1.67%, respectively. The proposed method was demonstrated to be efficient and time-saving, and had been applied to analyze monosaccharides in tobacco and tea successfully. Copyright © 2014 Elsevier B.V. All rights reserved.

  5. Four Pentasaccharide Resin Glycosides from Argyreia acuta

    Directory of Open Access Journals (Sweden)

    Bang-Wei Yu

    2017-03-01

    Full Text Available Four pentasaccharide resin glycosides, acutacoside F–I (1–4, were isolated from the aerial parts of Argyreia acuta. These compounds were characterized as a group of macrolactones of operculinic acid A, and their lactonization site of 11S-hydroxyhexadecanoic acid was esterified at the second saccharide moiety (Rhamnose at C-2. The absolute configuration of the aglycone was S. Their structures were elucidated by established spectroscopic and chemical methods.

  6. A new monoterpene glycoside from Siparuna thecaphora.

    Science.gov (United States)

    Vera Saltos, Mariela Beatriz; Naranjo Puente, Blanca Fabiola; Malafronte, Nicola; Braca, Alessandra

    2014-01-01

    Phytochemical investigation of the extracts of the leaves of Siparuna thecaphora (Poepp. et Endl.) A. DC. (Siparunaceae) allowed the isolation of one monoterpene glycoside, named trans-thujane-1α,7-diol 1-O-β-D-glucopyranoside (1) along with rutin, quercetin 3-O-β-D-glucopyranoside and 3,4-dihydroxybenzaldehyde. Their structural characterisation was obtained on the basis of extensive spectroscopic analyses, including 1D and 2D NMR experiments and HR-ESI-MS.

  7. Four Pentasaccharide Resin Glycosides from Argyreia acuta.

    Science.gov (United States)

    Yu, Bang-Wei; Sun, Jing-Jing; Pan, Jie-Tao; Wu, Xiu-Hong; Yin, Yong-Qin; Yan, You-Shao; Hu, Jia-Yan

    2017-03-11

    Four pentasaccharide resin glycosides, acutacoside F-I ( 1 - 4 ), were isolated from the aerial parts of Argyreia acuta . These compounds were characterized as a group of macrolactones of operculinic acid A, and their lactonization site of 11 S -hydroxyhexadecanoic acid was esterified at the second saccharide moiety (Rhamnose) at C-2. The absolute configuration of the aglycone was S . Their structures were elucidated by established spectroscopic and chemical methods.

  8. Characterisation and expression of monosaccharide transporters in lupins, Lupinus polyphyllus and L. albus.

    Science.gov (United States)

    Szenthe, A; Schäfer, H; Hauf, J; Schwend, T; Wink, M

    2007-11-01

    Monosaccharide transporter (MST) genes of Lupinus polyphyllus and L. albus were cloned, expressed and characterised. The isolation and functional characterisation of a cDNA clone and its corresponding genomic clone of a sugar transporter from L. polyphyllus (LpSTP1) is reported. Phylogenetic comparison of the nucleic and amino acid sequences showed the highest similarity to the AtSTP1 gene from Arabidopsis thaliana, which encodes a high affinity sugar transporter. The similar topology as well as the substrate specificity and expression pattern of LpSTP1 encoded protein additionally support the high similarity to the AtSTP1 gene product. The 1,590 bp LpSTP1 cDNA clone was heterologously expressed in yeast resulting in a fully functional specific sugar transporter. This transformation restored the viability of a yeast deletion mutant, which is devoid of all intrinsic MSTs and thus unable to take up and grow on hexose-containing media. The LpSTP1 protein is postulated to be a high-affinity MST since it supported growth best on media containing 0.2% hexose. Tissue-specific expression of LaSTP1 in L. albus was assayed by real-time PCR, which revealed that the lupin STP1 is mainly expressed in flower buds, flowers and young leaves. The results suggest that the main role of LaSTP1 is to catalyse monosaccharide import in sink tissues to meet increased carbohydrate demand during plant development.

  9. Oleandrin: A cardiac glycosides with potent cytotoxicity

    Science.gov (United States)

    Kumar, Arvind; De, Tanmoy; Mishra, Amrita; Mishra, Arun K.

    2013-01-01

    Cardiac glycosides are used in the treatment of congestive heart failure and arrhythmia. Current trend shows use of some cardiac glycosides in the treatment of proliferative diseases, which includes cancer. Nerium oleander L. is an important Chinese folk medicine having well proven cardio protective and cytotoxic effect. Oleandrin (a toxic cardiac glycoside of N. oleander L.) inhibits the activity of nuclear factor kappa-light-chain-enhancer of activated B chain (NF-κB) in various cultured cell lines (U937, CaOV3, human epithelial cells and T cells) as well as it induces programmed cell death in PC3 cell line culture. The mechanism of action includes improved cellular export of fibroblast growth factor-2, induction of apoptosis through Fas gene expression in tumor cells, formation of superoxide radicals that cause tumor cell injury through mitochondrial disruption, inhibition of interleukin-8 that mediates tumorigenesis and induction of tumor cell autophagy. The present review focuses the applicability of oleandrin in cancer treatment and concerned future perspective in the area. PMID:24347921

  10. CARDIAC GLYCOSIDES IN UP-TO-DATE CLINICAL PRACTICE

    Directory of Open Access Journals (Sweden)

    M. A. Gurevich

    2014-01-01

    Full Text Available The article reviews the use of cardiac glycosides in patients with chronic heart failure, paroxysmal tachyarrhythmia and chronic atrial fibrillation (rate control. According to the recent studies results cardiac glycosides may be substituted by angiotensin-converting enzyme inhibitors, angiotensin receptor antagonists, diuretics, calcium antagonists and beta-adrenoceptor blockers in order to decrease the risk of cardiac glycoside toxicity and, in some cases, to improve quality of life and prognosis of the patients.

  11. A New Phenolic Glycoside from the Barks of Cinnamomum cassia

    OpenAIRE

    Junfen Zeng; Yongbo Xue; Yongji Lai; Guangmin Yao; Zengwei Luo; Yonghui Zhang; Jinwen Zhang

    2014-01-01

    A new phenolic glycoside (1), named methyl 2-phenylpropanoate-2-O-β-D-apiofuranosyl-(1→6)-O-β-D–glucopyranoside, was isolated from the barks of Cinnamomum cassia, along with three known phenolic glycosides and four known lignan glycosides. The structure of 1 was elucidated by extensive interpretation of spectroscopic data and chemical method. Selected compounds were evaluated for their immunosuppressive activities against murine lymphocytes. Compounds 1, 2, 6 and 8 exhibited differential inhi...

  12. Bioactive Steroidal Glycosides from the Starfish Anasterias Minuta

    Directory of Open Access Journals (Sweden)

    H. Chludil

    2000-03-01

    Full Text Available Cytotoxic fractions obtained by purification of the ethanolic extract of Anasterias minuta contain sulfated hexasaccharide glycosides. These compounds show antifungal activity against Cladosporium cucumerinum.

  13. Prenylated flavonol glycosides Epimedium grandiflorum: Cytotoxicity and evaluation against inflammation and metabolic disorders

    Science.gov (United States)

    Two new prenylated flavonol glycosides, epimedigrandiosides A and B (1 and 2), and 28 previously known compounds including prenylated flavonol derivatives, flavonol glycoside, megastigmanes, phenyl alkanoids, sesquiterpenoid glycoside, lignan, and hexene glucoside were isolated from the methanol ext...

  14. Fermentable oligosaccharides, disaccharides, monosaccharides and polyols (FODMAPs) and nonallergic food intolerance: FODMAPs or food chemicals?

    Science.gov (United States)

    Gibson, Peter R.

    2012-01-01

    Food intolerance in irritable bowel syndrome (IBS) is increasingly being recognized, with patients convinced that diet plays a role in symptom induction. Evidence is building to implicate fermentable oligosaccharides, disaccharides, monosaccharides and polyols (FODMAPs) in the onset of abdominal pain, bloating, wind and altered bowel habit through their fermentation and osmotic effects. Hypersensitivity to normal levels of luminal distension is known to occur in patients with IBS, with consideration of food chemical intolerance likely to answer many questions about this physiological process. This paper summarizes the evidence and application of the most common approaches to managing food intolerance in IBS: the low-FODMAP diet, the elimination diet for food chemical sensitivity and others including possible noncoeliac gluten intolerance. PMID:22778791

  15. Molecular cloning, functional characterization and expression analysis of a novel monosaccharide transporter gene OsMST6 from rice (Oryza sativa L.)

    NARCIS (Netherlands)

    Wang, Y.; Xiao, Y.; Zhang, Y.; Chai, C.; Wei, G.; Wei, X.; Xu, H.; Wang, M.; Ouwerkerk, P.B.F.; Zhu, Z.

    2008-01-01

    Monosaccharides transporters play important roles in assimilate supply for sink tissue development. In this study, a new monosaccharide transporter gene OsMST6 was identified from rice (Oryza sativa L.). The predicted OsMST6 protein shows typical features of sugar transporters and shares 79.6%

  16. Monitoring glycation-induced structural and biofunctional changes in chicken immunoglobulin Y by different monosaccharides.

    Science.gov (United States)

    He, Zhenjiao; Tong, Chenyao; Sheng, Long; Ma, Meihu; Cai, Zhaoxia

    2016-11-01

    Chicken IgY has been applied in the food industry as an important supplement. Glycation of IgY is of special interest due to its possible influence on the structure and functionality of IgY. IgY was subjected to in vitro glycation with 4 different monosaccharides, including glucose (Glu), mannose (Man), fucose (Fuc), and fructose (Fru). The objective of this paper was to characterize the formation of IgY-sugar conjugates using ultraviolet spectra, fluorescence spectra, circular dichroism spectra, Fourier transform infrared spectra, and SDS-PAGE and differential scanning calorimetry analysis. The antigen epitopes of native and glycated IgY was determined by enzyme-linked immunosorbent assay (ELISA). The existence of broad bands in stacking gel and sample well demonstrated that reducing monosaccharides covalently bound to IgY. The secondary structure of IgY was altered from a well-defined β-sheet structure to a random coil structure. Fluorescence spectra showed that IgY was more hydrophilic after glycation. Thermal stability of glycated IgY was remarkably increased over that of native IgY. However, ELISA results would suggest that the antigen epitopes recognized by the polyclonal antibody and overall conformation changed in the IgY molecule due to a decrease in polyclonal antibody binding to glycated IgY. Data suggested that glycation induced by reducing sugars significantly affects the structure and antigen-binding ability of IgY, which could reduce the utility of IgY in certain applications. © 2016 Poultry Science Association Inc.

  17. Anticancer and Immunogenic Properties of Cardiac Glycosides

    Directory of Open Access Journals (Sweden)

    Naira Fernanda Zanchett Schneider

    2017-11-01

    Full Text Available Cardiac glycosides (CGs are natural compounds widely used in the treatment of several cardiac conditions and more recently have been recognized as potential antitumor compounds. They are known to be ligands for Na/K-ATPase, which is a promising drug target in cancer. More recently, in addition to their antitumor effects, it has been suggested that CGs activate tumor-specific immune responses. This review summarizes the anticancer aspects of CGs as new strategies for immunotherapy and drug repositioning (new horizons for old players, and the possible new targets for CGs in cancer cells.

  18. Two pentasaccharide resin glycosides from Argyreia acuta.

    Science.gov (United States)

    Yin, Yong-Qin; Pan, Jie-Tao; Yu, Bang-Wei; Cui, Hong-Hua; Yan, You-Shao; Chen, Yan-Fen

    2016-01-01

    Two new compounds of acutacosides 1 and 2, pentasaccharide resin glycosides were isolated from the aerial parts of Argyreia acuta. The core of the two compounds was operculinic acid A, and they were esterfied at the same position, just one substituent group was linked at C-2 of Rha. The absolute configuration of the aglycone in the two compounds was established by Mosher's method, which was (11S)-hydroxyhexadecanoic acid (jalapinolic acid). Their structures were established by a combination of spectroscopic and chemical methods.

  19. Cardenolide glycosides from Elaeodendron australe var. integrifolium.

    Science.gov (United States)

    Butler, Mark S; Towerzey, Leanne; Pham, Ngoc B; Hyde, Edward; Wadi, Sao Khemar; Guymer, Gordon P; Quinn, Ronald J

    2014-02-01

    Extracts from dried leaf and stems of Elaeodendron australe var. integrifolium (Celastraceae) collected in South East Queensland, Australia, were active in an assay that measured Ca(2+) driven expression of IL-2/luciferase designed to identify inhibitors of the ICRAC channel. Bioassay-guided isolation using C18 and polyamide column chromatography, HPLC (Phenyl and C18) and centrifugal partition chromatography (CPC) led to the isolation of digitoxigenin (1) and three cardenolide glycosides, glucoside 2, quinovoside 3 and the new natural product xyloside 4, as the active components with low nM activity in the reporter assay. Copyright © 2013 Elsevier Ltd. All rights reserved.

  20. Flavononol Glycosides of Reseda arabica (Resedaceae

    Directory of Open Access Journals (Sweden)

    Djemaa Berrehal

    2012-07-01

    Full Text Available Five flavonol glycosides, kaempferol 3,7-di-O- α -L-rhamnopyranoside (1 , isorhamnetin 3,7-di-O- α -L-rhamnopyranoside (2 , kaempferol 3-O- β -D-glucopyranoside-7-O- α -L-rhamnopyranoside (3 , isorhamnetin 3-O- β -D-glucopyranoside-7-O- α -L-rhamnopyranoside (4, Kaempferol 3-O- β -xylopyranosyl-(1'''→2''-O- α -L-rhamnopyranoside-7-O- α -L-rhamnopyranoside (5, have been isolated from the aerial parts of Reseda arabica. Their structures were established on the basis of physical and spectroscopic analysis, and by comparison with the literature data.

  1. Enantiomeric Excess Determination for Monosaccharides Using Chiral Transmission to Cold Gas-Phase Tryptophan in Ultraviolet Photodissociation

    Science.gov (United States)

    Fujihara, Akimasa; Maeda, Naoto; Doan, Thuc N.; Hayakawa, Shigeo

    2017-02-01

    Chiral transmission between monosaccharides and amino acids via photodissociation in the gas phase was examined using a tandem mass spectrometer fitted with an electrospray ionization source and a cold ion trap in order to investigate the origin of the homochirality of biomolecules in molecular clouds. Ultraviolet photodissociation mass spectra of cold gas-phase noncovalent complexes of the monosaccharide enantiomers glucose (Glc) and galactose (Gal) with protonated l-tryptophan H+( l-Trp) were obtained by photoexcitation of the indole ring of l-Trp. l-Trp dissociated via Cα-Cβ bond cleavage when noncovalently complexed with d-Glc; however, no dissociation of l-Trp occurred in the homochiral H+( l-Trp)( l-Glc) noncovalent complex, where the energy absorbed by l-Trp was released through the evaporation of l-Glc. This enantioselective photodissociation of Trp was due to the transmission of chirality from Glc to Trp via photodissociation in the gas-phase noncovalent complexes, and was applied to the quantitative chiral analysis of monosaccharides. The enantiomeric excess of monosaccharides in solution could be determined by measuring the relative abundance of the two product ions in a single photodissociation mass spectrum of the cold gas-phase noncovalent complex with H+( l-Trp), and by referring to the linear relationships derived in this work.

  2. Separation of phenolic acids from monosaccharides by low-pressure nanofiltration integrated with laccase pre-treatments

    DEFF Research Database (Denmark)

    Luo, Jianquan; Zeuner, Birgitte; Morthensen, Sofie Thage

    2015-01-01

    Separation of phenolic acids from monosaccharides is required for detoxification of lignocellulosic hydrolysates. For the first time, a low-pressure nanofiltration (NF) process was used to retain phenolic acids (vanillic acid, p-coumaric acid and ferulic acid) and at the same time permeate...

  3. Transformation behaviour and residual stresses in welding of new LTT filler materials; Umwandlungsverhalten und Eigenspannungen beim Schweissen neuartiger LTT-Zusatzwerkstoffe

    Energy Technology Data Exchange (ETDEWEB)

    Kromm, Arne

    2011-07-06

    is seen to occur. This is observed for the considered alloys to be particularly pronounced in transverse direction of the weld. By contrast, the residual stress level in longitudinal weld direction is nearly independent of the shrinkage conditions. With the help of residual stress depth gradients it could be established that the additional shrinkage restraint manifests itself in a parallel shift of the residual stress level in the weld metal. Application of energy-dispersive diffraction methods additionally allowed it for the first time to determine residual stresses in the austenitic phase of the LTT alloy which is present parallel to martensite. Results gained under laboratory conditions mostly need to be verified under real fabrication conditions. For this purpose, a component weld test was performed in a special large-scale testing facility. Under structural shrinkage restraint, the load relieving effect of a specific LTT welding filler material could be proven by means of a pronounced stress reduction duringwelding. Overall, evidence was furnished that the concept of Low Transformation Temperature (LTT)alloys is successful and that the proven austenite-martensite transformation exerts a significanteffect on the residual stress level. [German] Die Erkenntnis, dass die Phasenumwandlung bei der Schweisseigenspannungsentstehung hochfester Staehle eine bedeutende Rolle spielt, gibt es bereits seit langer Zeit. Bisher existierten jedoch keine Ansaetze, diesen Effekt praktisch zur Schweisseigenspannungskontrolle zu nutzen. Neuartige Low Transformation Temperature (LTT) Legierungen bieten aufgrund ihrer charakteristischen chemischen Zusammensetzung die Moeglichkeit, hochfeste Staehle auf deren Festigkeitsniveau zu fuegen. Die martensitische Phasenumwandlung soll zudem eine gezielte Einstellung der Schweisseigenspannungen erlauben. Die im Schrifttum vorliegenden Untersuchungen zu diesem Thema sind zwar zahlreich, bieten jedoch nur wenige Erkenntnisse zur Wechselwirkung

  4. Antidiabetic effect of crude glycoside of abrus precatorius in alloxan ...

    African Journals Online (AJOL)

    The antidiabetic effect of crude a glycoside from Abrus precatorius seed was studied in alloxan diabetic rabbits. Three groups of male alloxan diabetic rabbits were used. The three groups (n = 3) received oral injection of 50mg/kg body of crude glycoside (CG), chlorpropamide (CP)-a known synthetic antidiabetic drug and ...

  5. Steroidal glycosides from the roots of Asclepias curassavica.

    Science.gov (United States)

    Warashina, Tsutomu; Noro, Tadataka

    2008-03-01

    Twenty-six new acylated-oxypregnane glycosides were obtained along with three known cardenolide glycosides from the roots of Asclepias curassavica (Asclepiadaceae). The new compounds were confirmed to contain 12-O-benzoylsarcostin, 12-O-benzoyldeacylmetaplexigenin, kidjolanin, and 12-O-benzoyltayloron, and one new acylated-oxypregnane, 12-O-(E)-cinnamoyltayloron, as their aglycones, using both spectroscopic and chemical methods.

  6. Caffeoyl phenylethanoid glycosides in Sanango racemosum and in the gesneriaceae

    DEFF Research Database (Denmark)

    Jensen, Søren Rosendal

    1996-01-01

    An investigation of Samango racemosum for systematically useful glycosides has been performed. No iridoids could be detected, but reverse phase chromatography provided the caffeoyl phenylethanoid glycosides (CPGs) calceolarioside C and conandroside together with the new 2-(3,4-dihydroxyphenyl)eth...

  7. Evaluating the Cancer Therapeutic Potential of Cardiac Glycosides

    Directory of Open Access Journals (Sweden)

    José Manuel Calderón-Montaño

    2014-01-01

    Full Text Available Cardiac glycosides, also known as cardiotonic steroids, are a group of natural products that share a steroid-like structure with an unsaturated lactone ring and the ability to induce cardiotonic effects mediated by a selective inhibition of the Na+/K+-ATPase. Cardiac glycosides have been used for many years in the treatment of cardiac congestion and some types of cardiac arrhythmias. Recent data suggest that cardiac glycosides may also be useful in the treatment of cancer. These compounds typically inhibit cancer cell proliferation at nanomolar concentrations, and recent high-throughput screenings of drug libraries have therefore identified cardiac glycosides as potent inhibitors of cancer cell growth. Cardiac glycosides can also block tumor growth in rodent models, which further supports the idea that they have potential for cancer therapy. Evidence also suggests, however, that cardiac glycosides may not inhibit cancer cell proliferation selectively and the potent inhibition of tumor growth induced by cardiac glycosides in mice xenografted with human cancer cells is probably an experimental artifact caused by their ability to selectively kill human cells versus rodent cells. This paper reviews such evidence and discusses experimental approaches that could be used to reveal the cancer therapeutic potential of cardiac glycosides in preclinical studies.

  8. Diarylheptanoid Glycosides of Morella salicifolia Bark

    Directory of Open Access Journals (Sweden)

    Edna Makule

    2017-12-01

    Full Text Available A methanolic extract of Morella salicifolia bark was fractionated by various chromatographic techniques yielding six previously unknown cyclic diarylheptanoids, namely, 7-hydroxymyricanol 5-O-β-d-glucopyranoside (1, juglanin B 3-O-β-d-glucopyranoside (2, 16-hydroxyjuglanin B 17-O-β-d-glucopyranoside (3, myricanone 5-O-β-d-gluco-pranosyl-(1→6-β-d-glucopyranoside (4, neomyricanone 5-O-β-d-glucopranosyl-(1→6-β-d-glucopyranoside (5, and myricanone 17-O-α-l-arabino-furanosyl-(1→6-β-d-glucopyranoside (6, respectively, together with 10 known cyclic diarylheptanoids. The structural diversity of the diarylheptanoid pattern in M. salicifolia resulted from varying glycosidation at C-3, C-5, and C-17 as well as from substitution at C-11 with hydroxy, carbonyl or sulfate groups, respectively. Structure elucidation of the isolated compounds was achieved on the basis of one- and two-dimensional nuclear magnetic resonance (NMR as well as high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS analyses. The absolute configuration of the glycosides was confirmed after hydrolysis and synthesis of O-(S-methyl butyrated (SMB sugar derivatives by comparison of their 1H-NMR data with those of reference sugars. Additionally, absolute configuration of diarylheptanoid aglycones at C-11 was determined by electronic circular dichroism (ECD spectra simulation and comparison with experimental CD spectra after hydrolysis.

  9. Glycosides, Depression and Suicidal Behaviour: The Role of Glycoside-Linked Proteins

    Directory of Open Access Journals (Sweden)

    Yogesh Dwivedi

    2011-03-01

    Full Text Available Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably they can have a presynaptic facilitatory effect, through the activation of several intracellular signaling pathways that include molecules like protein kinase A, Rap-1, cAMP, cADPR and G proteins. These proteins take part in a myriad of brain functions such as cell survival and synaptic plasticity. In depressed suicide victims, it has been found that their activity is strongly decreased, primarily in hippocampus and prefrontal cortex. These studies suggest that glycosides can regulate neuroprotection through Rap-1 and other molecules, and may play a crucial role in the pathophysiology of depression and suicide.

  10. Acylated flavonol glycoside from Platanus orientalis.

    Science.gov (United States)

    Tantry, Mudasir A; Akbar, Seema; Dar, Javid A; Irtiza, Syed; Galal, Ahmed; Khuroo, Mohammad A; Ghazanfar, Khalid

    2012-03-01

    The ethylacetate and n-butanol fractions of ethanolic extract of Platanus orientalis leaves led to the isolation of new acylated flavonol glycoside as 3',5,7-trihydroxy-4'-methoxyflavonol 3-[O-2-O-(2,4-Dihydroxy)-E-cinnamoyl-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl (1→2)]-β-D-glucopyranoside, along with seven known compounds. All the compounds were characterized by NMR including 2D NMR techniques. The isolates were evaluated for NF-κB, nitric oxide (NO), aromatase and QR2 chemoprevention activities and some of them appeared to be modestly active. Crown Copyright © 2011. Published by Elsevier B.V. All rights reserved.

  11. Antioxidant phenylpropanoid glycosides from Buddleja davidii.

    Science.gov (United States)

    Ahmad, Ijaz; Ahmad, Nisar; Wang, Fanghai

    2009-08-01

    Phytochemical investigations on the n-BuOH-soluble fraction of the whole plant of Buddleja davidii led to the isolation of the phenylpropanoid glycosides 1-10. Their structures were determined by 1D and 2D NMR spectroscopic techniques. All the compounds showed potent antioxidative activity in three different tests, with IC(50) values in the range 4.15-9.47 microM in the hydroxyl radical ( OH) inhibitory activity test, 40.32-81.15 microM in the total ROS (reactive oxygen species) inhibitory activity test, and 2.26-7.79 microM in the peroxynitrite (ONOO(-)) scavenging activity test. Calceolarioside A (1) displayed the strongest scavenging potential with IC(50) values of (4.15 +/- 0.07, 40.32 +/- 0.09, 2.26 +/- 0.03 microM) for OH, total ROS and scavenging of ONOO(-), respectively.

  12. Cyanogenic glycosides: a case study for evolution and application of cytochromes P450

    DEFF Research Database (Denmark)

    Bak, Søren; Paquette, Susanne Michelle; Morant, Marc

    2006-01-01

    Cyanogenic glycosides are ancient biomolecules found in more than 2,650 higher plant species as well as in a few arthropod species. Cyanogenic glycosides are amino acid-derived β-glycosides of α-hydroxynitriles. In analogy to cyanogenic plants, cyanogenic arthropods may use cyanogenic glycosides ...

  13. Determination of molecular weights and monosaccharide compositions in Abelmoschus manihot polysaccharides

    Science.gov (United States)

    Wang, Xuemei; Wang, Yingying; Wu, Mimi; Zhang, Xiuzhen

    2012-09-01

    Abelmoschus manihot polysaccharide, AMP-1, AMP-2, AMP-3, and AMP-4, were purified from four kinds of Abelmoschus manihot gum (AMG). The molecular weights and monosaccharide compositions of AMP-1, AMP-2, AMP-3 and AMP-4 were characterized by gel permeation chromatography, Fourier transform-infrared spectroscopy and high performance anion-exchange chromatography with pulsed amperometric detection. Results indicated that the molecular weights of AMP-1, AMP-2, AMP-3, and AMP-4 were approximately 3.91 × 103, 5.36 × 105, 3.87 × 103, and 5.12 × 105 Da, respectively. The Abelmoschus manihot polysaccharide was mainly composed of galactose, glucose and mannose with the molar ratios at 0.29: 1.00: 0.41 (AMP-1), 0.56: 0.13: 1.00 (AMP-2), 0.10: 1.00: 0.11 (AMP-3) and 0.55: 0.17: 1.00 (AMP-4), respectively.

  14. Novel monosaccharide fermentation products in Caldicellulosiruptor saccharolyticus identified using NMR spectroscopy

    Energy Technology Data Exchange (ETDEWEB)

    Isern, Nancy G.; Xue, Junfeng; Rao, Jaya V.; Cort, John R.; Ahring, Birgitte K.

    2013-04-03

    Profiles of metabolites produced by the thermophilic obligately anaerobic cellulose-degrading Gram-positive bacterium Caldicellulosiruptor saccharolyticus DSM 8903 strain following growth on different monosaccharides (D-glucose, D-mannose, L-arabinose, D-arabinose, D-xylose, L-fucose, and D-fucose) as carbon sources revealed several unexpected fermentation products, suggesting novel metabolic capacities and unexplored metabolic pathways in this organism. Both 1H and 13C nuclear magnetic resonance (NMR) spectroscopy were used to determine intracellular and extracellular metabolite profiles. Metabolite profiles were determined from 1-D 1H NMR spectra by curve fitting against spectral libraries provided in Chenomx software. To reduce uncertainties due to unassigned, overlapping, or poorly-resolved peaks, metabolite identifications were confirmed with 2-D homonuclear and heteronuclear NMR experiments. In addition to expected metabolites such as acetate, lactate, glycerol, and ethanol, several novel fermentation products were identified: ethylene glycol (from growth on D-arabinose, though not L-arabinose), acetoin and 2,3-butanediol (from D-glucose and L-arabinose), and hydroxyacetone (from D-mannose and L-arabinose). Production of ethylene glycol from D-arabinose was particularly notable, with around 10% of the substrate carbon converted into this uncommon fermentation product. The novel products have not previously been reported to be produced by C. saccharolyticus, nor would they be easily predicted from the current genome annotation, and show new potentials for using this strain for production of bioproducts.

  15. Production of monosaccharides from napier grass by hydrothermal process with phosphoric acid.

    Science.gov (United States)

    Takata, Eri; Tsutsumi, Ken; Tsutsumi, Yuji; Tabata, Kenji

    2013-09-01

    The production of monosaccharides from napier grass was investigated in the presence of acid catalysts using the hydrothermal process. When the napier grass was treated with 3 wt.% phosphoric acid at 160°C for 15min, the xylose yield reached 10.3 wt.%, corresponding to 72.0% of the xylan in it, whereas glucose was hardly obtained. A combined process was then conducted using an 85 wt.% phosphoric acid treatment at 60 °C for 1h followed by a hydrothermal treatment with 3 wt.% phosphoric acid. In the initial treatment with concentrated phosphoric acid the most of xylan was hydrolyzed to xylose, and the crystalline cellulose was converted to its amorphous form. The hydrolysis of cellulose to glucose was significantly enhanced during the following hydrothermal process with 3 wt.% phosphoric acid at 200 °C for 8 min. Consequently, 77.2% yield of xylose and 50.0% yield of glucose were obtained from the combined process. Copyright © 2013 Elsevier Ltd. All rights reserved.

  16. Simultaneous determination of monosaccharides and oligosaccharides in dates using liquid chromatography-electrospray ionization mass spectrometry.

    Science.gov (United States)

    Ghfar, Ayman A; Wabaidur, Saikh M; Ahmed, A Yacine Badjah Hadj; Alothman, Zeid A; Khan, Mohammad R; Al-Shaalan, Nora H

    2015-06-01

    Ultra performance liquid chromatography coupled to mass spectrometry was used for the simultaneous separation and determination of reducing monosaccharides (fructose and glucose), a non-reducing disaccharide (sucrose) and oligosaccharides (kestose and nystose) in HILIC mode. The chromatographic separation of all saccharides was performed on a BEH amide column using an acetonitrile-water gradient elution. The detection was carried out using selected ion recording (SIR) acquisition mode. The validation of the proposed method showed that the limit of detection and limit of quantification values for the five analyzed compounds were in the range of 0.25-0.69μg/mL and 0.82-3.58μg/mL, respectively; while the response was linear in the range of 1-50μg/mL. The developed method showed potential usefulness for a rapid and sensitive analysis of underivatized saccharides and was used for determination of sugars in three date samples (Sefri, Mabroom, Ghassab) which were soxhlet extracted by ethanol. Copyright © 2014 Elsevier Ltd. All rights reserved.

  17. Recent advances in capillary electrophoresis separation of monosaccharides, oligosaccharides, and polysaccharides.

    Science.gov (United States)

    Mantovani, Veronica; Galeotti, Fabio; Maccari, Francesca; Volpi, Nicola

    2018-01-01

    This article illustrates the basis and applications of methodologies for the analysis of simple and complex carbohydrates by means of CE. After a description of the most common and novel approaches useful for the analysis and characterization of carbohydrates, this review covers the recent advances in CE separation of monosaccharides, oligosaccharides, and polysaccharides. Various CE techniques are also illustrated for the study of carbohydrates derived from complex glyco-derivatives such as glycoproteins and glycolipids, essential for biopharmaceutical and glycoproteomics applications as well as for biomarker detection. Most glycans have no significant UV absorption, and derivatization with fluorophore groups prior to separation usually results in higher sensitivity and an improved electrophoretic profile. We also discuss the recent applications and separations by CE of derivatized simple and more complex carbohydrates with different chromophoric active tags. Overall, this review aims to give an overview of the most recent state-of-the-art techniques used in carbohydrate analysis by CE. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  18. Chronic lactose intake modifies the gastric emptying of monosaccharides but not of disaccharides in weanling rats

    Directory of Open Access Journals (Sweden)

    E.A.L. da-Costa-Pinto

    1997-06-01

    Full Text Available Ninety-six weanling male Wistar rats were fed for four weeks one of two different chows: a normal rat chow containing 55.5% (w/w starch (control group, N = 48 or a rat chow in which starch was partially replaced by lactose, in such a way that the experimental group (N = 48 received 35.5% (w/w starch and 20% (w/w lactose. The gastric emptying of fluid was then studied by measuring the gastric retention of four test meals containing lactose (5% or 10%, w/v or glucose + galactose (5% or 10%, w/v. Homogenates of the small intestine were assayed for lactase activity. The gastric retention values were obtained 15 min after orogastric infusion of the liquid meals. The median values for gastric retention of the 5% lactose solutions were 37.7% for the control group and 37.0% for the experimental group (P>0.02. For the 10% lactose solution the median values were 51.2% and 47.9% (P>0.02 for the control and experimental groups, respectively. However, for the 2.5% glucose + 2.5% galactose meal the median gastric retention was lower (P0.05. These results suggest that the prolonged ingestion of lactose by young adult rats changes the gastric emptying of a solution containing 5% monosaccharides. This adaptation may reflect the desensitization of intestinal nutrient receptors, possibly by an osmotic effect of lactose present in the chow.

  19. Synthesis and sensory evaluation of ent-kaurane diterpene glycosides.

    Science.gov (United States)

    Prakash, Indra; Campbell, Mary; San Miguel, Rafael Ignacio; Chaturvedula, Venkata Sai Prakash

    2012-07-26

    Catalytic hydrogenation of the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana, namely rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)₂ and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data and chemical studies. Also, we report herewith the sensory evaluation of all the reduced compounds against their corresponding original steviol glycosides and sucrose for the sweetness property of these molecules.

  20. TRITERPENE GLYCOSIDES OF HERB OF SOLIDAGO CAUCASICA KEM.-NATH.

    Directory of Open Access Journals (Sweden)

    V. V. Fedotova

    2014-01-01

    Full Text Available Species of the Solidago genus are used to treat diseases of the urinary system but we study Solidago caucasica for the first time. The aim of this work is to study triterpene glycosides of Solidago caucasica. Spectrophotometry revealed that the triterpene glycosides in herb of Solidago caucasica are derivants of oleanolic acid. The quantitative determination of the amount of triterpene glycosides in the Solidago caucasica herb was done by gravimetric method (content is 0,93% and UV spectrophotometry, based on oleanolic acid (content is 1,01 ± 0,03%.

  1. Steroidal Glycosides from the Rhizomes of Ruscus hypoglossum

    OpenAIRE

    Yoshinori, MIMAKI; Minpei, KURODA; Yuusuke, OBATA; Yutaka, SASHIDA; School of Pharmacy, Tokyo University of Pharmacy and Life Science; School of Pharmacy, Tokyo University of Pharmacy and Life Science; School of Pharmacy, Tokyo University of Pharmacy and Life Science; School of Pharmacy, Tokyo University of Pharmacy and Life Science

    1999-01-01

    Eight steroidal glycosides (1-8), including two new compounds (7 and 8), were isolated from the rhizomes oiRuscus hypoglossum. The structures of the new glycosides were characterized as (25R)-spirost-5-ene-1β,3β-diol 1-O-{O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-6-0-acetyl-β-D-galactopyranoside} (7) and (22S)-cholest-5-ene-1β,3β,16β,22-tetrol 1-O-α-L-arabinopyranosyl 16-O-α-L-rhamnopyranoside (8). Compound 8 is the first cholestane glycoside isolated from a plant of the genus Ru...

  2. A new phenolic glycoside from the barks of Cinnamomum cassia.

    Science.gov (United States)

    Zeng, Junfen; Xue, Yongbo; Lai, Yongji; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui; Zhang, Jinwen

    2014-10-31

    A new phenolic glycoside (1), named methyl 2-phenylpropanoate-2-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside, was isolated from the barks of Cinnamomum cassia, along with three known phenolic glycosides and four known lignan glycosides. The structure of 1 was elucidated by extensive interpretation of spectroscopic data and chemical method. Selected compounds were evaluated for their immunosuppressive activities against murine lymphocytes. Compounds 1, 2, 6 and 8 exhibited differential inhibition against ConA-induced T cells proliferation.

  3. A New Phenolic Glycoside from the Barks of Cinnamomum cassia

    Directory of Open Access Journals (Sweden)

    Junfen Zeng

    2014-10-01

    Full Text Available A new phenolic glycoside (1, named methyl 2-phenylpropanoate-2-O-β-D-apiofuranosyl-(1→6-O-β-D–glucopyranoside, was isolated from the barks of Cinnamomum cassia, along with three known phenolic glycosides and four known lignan glycosides. The structure of 1 was elucidated by extensive interpretation of spectroscopic data and chemical method. Selected compounds were evaluated for their immunosuppressive activities against murine lymphocytes. Compounds 1, 2, 6 and 8 exhibited differential inhibition against ConA-induced T cells proliferation.

  4. Effects of culture conditions on monosaccharide composition of Ganoderma lucidum exopolysaccharide and on activities of related enzymes.

    Science.gov (United States)

    Peng, Lin; Qiao, Shuangkui; Xu, Zhenghong; Guan, Feng; Ding, Zhongyang; Gu, Zhenghua; Zhang, Liang; Shi, Guiyang

    2015-11-20

    We investigated the relationship between monosaccharide composition of Ganoderma lucidum exopolysaccharide (EPS) and activities of EPS synthesis enzymes under various culture temperatures and initial pH values. The mole percentages of three major EPS monosaccharides, glucose, galactose and mannose, varied depending on culture conditions and the resulting EPS displayed differing anti-tumor activities. In nine tested enzymes, higher enzyme activities were correlated with higher temperature and lower initial pH. Altered mole percentages of galactose and mannose under various culture conditions were associated with activities of α-phosphoglucomutase (PGM) and phosphoglucose isomerase (PGI), respectively, and that of mannose was also associated with phosphomannose isomerase (PMI) activity only under various pH. Our findings suggest that mole percentages of G. lucidum EPS monosaccharides can be manipulated by changes of culture conditions that affect enzyme activities, and that novel fermentation strategies based on this approach may enhance production and biological activity of EPS. Copyright © 2015 Elsevier Ltd. All rights reserved.

  5. Isolation Of A Stilbene Glycoside And Other Constituents Of ...

    African Journals Online (AJOL)

    ... acid arjungenin and a mixture of β-sitosterol and stigmasterol. Structure determination of the isolated compounds was achieved on the basis of spectroscopic measurements. Keywords: Terminalia sericeae, stilbenes, combretastatin, resveratrol, glycosides. African Journal of Traditional and Complementary Medicine Vol.

  6. Resin glycosides from the aerial parts of Operculina turpethum.

    Science.gov (United States)

    Ding, Wenbing; Jiang, Zi-Hua; Wu, Ping; Xu, Liangxiong; Wei, Xiaoyi

    2012-09-01

    Three glycosidic acids, turpethic acids A-C, and two intact resin glycosides, turpethosides A and B, all having a common pentasaccharide moiety and 12-hydroxy fatty acid aglycones of different chain lengths, were obtained from the aerial parts of Operculina turpethum. Their structures were elucidated by spectroscopic analyses and chemical correlations. The aglycones were characterized as 12-hydroxypentadecanoic acid in two compounds, 12-hydroxyhexadecanoic acid in two other components, and 12-hydroxyheptadecanoic acid in the fifth compound, which were all confirmed by synthesis. The absolute configurations of these aglycones were all established as S by Mosher's method. These compounds represent the first examples of resin glycosides with a monohydroxylated 12-hydroxy fatty acid as an aglycone, and one compound is the first described resin glycoside having a hydroxylated C(17) fatty acid as its aglycone. Copyright © 2012 Elsevier Ltd. All rights reserved.

  7. Anti-neutrophilic inflammatory steroidal glycosides from Solanum torvum.

    Science.gov (United States)

    Lee, Chia-Lin; Hwang, Tsong-Long; He, Wan-Jung; Tsai, Yi-Hong; Yen, Chiao-Ting; Yen, Hsin-Fu; Chen, Chao-Jung; Chang, Wei-Yi; Wu, Yang-Chang

    2013-11-01

    Torvpregnanosides A and B, two pregnane glycosides, and torvoside Q, a 23-keto-spirostanol glycoside, along with twelve known steroidal saponins were isolated from aerial parts of Solanum torvum. Of the latter, four of the 23-hydroxy-spirostanol glycosides, and, a yamogenin glycoside, were in this plant discovered. All structures were identified from spectroscopic data, and all the compounds were tested for in vitro anti-neutrophilic inflammatory activity. Two compounds showed selective inhibition against elastase release and superoxide anion generation, respectively, by human neutrophils with IC50 values of 5.66 and 3.59 μM, while two others inhibited both inflammatory mediators with IC50 values of 0.66-3.49 μM. Structure-activity relationships are discussed. Copyright © 2013. Published by Elsevier Ltd.

  8. New benzophenone and quercetin galloyl glycosides from Psidium guajava L.

    Science.gov (United States)

    Matsuzaki, Keiichi; Ishii, Rie; Kobiyama, Kaori

    2010-01-01

    New benzophenone and flavonol galloyl glycosides were isolated from an 80% MeOH extract of Psidium guajava L. (Myrtaceae) together with five known quercetin glycosides. The structures of the novel glycosides were elucidated to be 2,4,6-trihydroxybenzophenone 4-O-(6″-O-galloyl)-β-d-glucopyranoside (1, guavinoside A), 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6″-O-galloyl)-β-d-glucopyranoside (2, guavinoside B), and quercetin 3-O-(5″-O-galloyl)-α-l-arabinofuranoside (3, guavinoside C) by NMR, MS, UV, and IR spectroscopies. Isolated phenolic glycosides showed significant inhibitory activities against histamine release from rat peritoneal mast cells, and nitric oxide production from a murine macrophage-like cell line, RAW 264.7. PMID:20354804

  9. Three new caffeoyl glycosides from the roots of Picrorhiza scrophulariiflora.

    Science.gov (United States)

    Zhu, Tong Fei; Huang, Kai Yi; Deng, Xu Ming; Zhang, Yu; Xiang, Hua; Gao, Hui Yuan; Wang, Da Cheng

    2008-03-27

    From the underground parts of Picrorhiza scrophulariiflora, three new caffeoyl glycosides, scrocaffeside A-C (1-3), together with two caffeic acid derivates, 4-O-beta-D-glucopyranosyl caffeic acid (4) and 4-methoxy caffeic acid (5) and a phenylethanoid glycoside, scroside D (6), were isolated. Their structures were elucidated on the basis of chemical and spectroscopic evidence and comparisons with literature data of related compounds.

  10. Synthesis and Sensory Evaluation of ent-Kaurane Diterpene Glycosides

    OpenAIRE

    Venkata Sai Prakash Chaturvedula; Rafael Ignacio San Miguel; Indra Prakash; Mary Campbell

    2012-01-01

    Catalytic hydrogenation of the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana, namely rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)2 and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral...

  11. A new phenolic glycoside from Cnidium monnieri fruits.

    Science.gov (United States)

    Kim, Seon Beom; Chang, Bo Yoon; Han, Sang-Bae; Hwang, Bang Yeon; Kim, Sung Yeon; Lee, Mi Kyeong

    2013-01-01

    A new phenolic glycoside, methylpicraquassioside B (6), together with nine known glycosides, cnidioside A (1), cnidioside B (2), picraquassioside A (3), methylpicraquassioside A (4), picraquassioside B (5), xanthotoxol-8-β-glucoside (7), 5-methoxy-xanthotoxol-8-β-glucoside (8), 8-methoxy-xanthotoxol-5-β-glucoside (9) and marmesinin (10) were isolated from n-BuOH-soluble fraction of Cnidium monnieri fruits. All the isolated compounds, however, exerted little immunomodulatory effect in RAW 264.7 cells.

  12. Three new sulphur glycosides from the seeds of Descurainia sophia.

    Science.gov (United States)

    Feng, Wei-Sheng; Li, Chun-Ge; Zheng, Xiao-Ke; Li, Ling-Ling; Chen, Wen-Jing; Zhang, Yan-Li; Cao, Yan-Gang; Gong, Jian-Hong; Kuang, Hai-Xue

    2016-08-01

    Three new sulphur glycosides, raphanuside B-D (1-3), together with a known sulphur glycoside, raphanuside (4) were isolated from the decoction of the seeds of Descurainia sophia (L.) Webb ex Prantl, and the compound 4 was reported for the first time from this plant. Their structures were identified by means of UV, IR, 1D, 2D NMR (HSQC, HMBC and NOESY) and HR-ESI-MS spectroscopic data.

  13. Heterogeneity in the expression and subcellular localization of POLYOL/MONOSACCHARIDE TRANSPORTER genes in Lotus japonicus.

    Directory of Open Access Journals (Sweden)

    Lu Tian

    Full Text Available Polyols can serve as a means for the translocation of carbon skeletons and energy between source and sink organs as well as being osmoprotective solutes and antioxidants which may be involved in the resistance of some plants to biotic and abiotic stresses. Polyol/Monosaccharide transporter (PLT proteins previously identified in plants are involved in the loading of polyols into the phloem and are reported to be located in the plasma membrane. The functions of PLT proteins in leguminous plants are not yet clear. In this study, a total of 14 putative PLT genes (LjPLT1-14 were identified in the genome of Lotus japonicus and divided into 4 clades based on phylogenetic analysis. Different patterns of expression of LjPLT genes in various tissues were validated by qRT-PCR analysis. Four genes (LjPLT3, 4, 11, and 14 from clade II were expressed at much higher levels in nodule than in other tissues. Moreover, three of these genes (LjPLT3, 4, and 14 showed significantly increased expression in roots after inoculation with Mesorhizobium loti. Three genes (LjPLT1, 3, and 9 responded when salinity and/or osmotic stresses were applied to L. japonicus. Transient expression of GFP-LjPLT fusion constructs in Arabidopsis and Nicotiana benthamiana protoplasts indicated that the LjPLT1, LjPLT6 and LjPLT7 proteins are localized to the plasma membrane, but LjPLT2 (clade IV, LjPLT3, 4, 5 (clade II and LjPLT8 (clade III proteins possibly reside in the Golgi apparatus. The results suggest that members of the LjPLT gene family may be involved in different biological processes, several of which may potentially play roles in nodulation in this nitrogen-fixing legume.

  14. Steroid glycosides from the starfish Pentaceraster gracilis.

    Science.gov (United States)

    Vien, Le Thi; Ngoan, Bui Thi; Hanh, Tran Thi Hong; Vinh, Le Ba; Thung, Do Cong; Thao, Do Thi; Thanh, Nguyen Van; Cuong, Nguyen Xuan; Nam, Nguyen Hoai; Kiem, Phan Van; Minh, Chau Van

    2017-05-01

    Using combined chromatographic separations, two new steroid glycosides namely pentacerosides A (1) and B (2), and four known compounds were isolated from the methanol extract of the starfish Pentaceraster gracilis. Their structures were determined on the basis of spectroscopic data ((1)H and (13)C NMR, HSQC, HMBC, (1)H-(1)H COSY, ROESY, and FT-ICR-MS) and by comparing obtained results to the literature values. Among the isolated compounds, only maculatoside (5) showed significant cytotoxic effect against Hep-G2 (IC50 = 16.75 ± 0.69 μM) and SK-Mel2 (IC50 = 19.44 ± 1.45 μM) cell lines and moderate effect on KB (IC50 = 36.53 ± 0.78 μM), LNCaP (IC50 = 39.75 ± 3.34 μM), and MCF7 (IC50 = 47.34 ± 7.01 μM) cell lines.

  15. Antioxidant flavonol glycosides from Schinus molle.

    Science.gov (United States)

    Marzouk, Mohamed S; Moharram, Fatma A; Haggag, Eman G; Ibrahim, Magda T; Badary, Osama A

    2006-03-01

    Chromatographic separation of aqueous MeOH extract of the leaves of Schinus molle L. has yielded two new acylated quercetin glycosides, named isoquercitrin 6''-O-p-hydroxybenzoate (12) and 2''-O-alpha-L-rhamnopyranosyl-hyperin 6''-O-gallate (13), together with 12 known polyphenolic metabolites for the first time from this species, namely gallic acid (1), methyl gallate (2), chlorogenic acid (3), 2''-alpha-L-rhamnopyranosyl-hyperin (4), quercetin 3-O-beta-D-neohesperidoside (5), miquelianin (6), quercetin 3-O-beta-D-galacturonopyranoside (7), isoquercitrin (8), hyperin (9), isoquercitrin 6''-gallate (10), hyperin 6''-O-gallate (11) and (+)-catechin (14). Their structures were established on the basis of chromatographic properties, chemical, spectroscopic (UV, 1H, 13C NMR) and ESI-MS (positive and negative modes) analyses. Compounds 4-9 and 11 exhibited moderate to strong radical scavenging properties on lipid peroxidation, hydroxyl radical and superoxide anion generations with the highest activities shown by 6 and 7 in comparison with that of quercetin as a positive control in vitro. Copyright 2006 John Wiley & Sons, Ltd.

  16. Human intestinal hydrolysis of phenol glycosides - a study with quercetin and p-nitrophenol glycosides using ileostomy fluid.

    Science.gov (United States)

    Knaup, Bastian; Kahle, Kathrin; Erk, Thomas; Valotis, Anagnostis; Scheppach, Wolfgang; Schreier, Peter; Richling, Elke

    2007-11-01

    In order to study the influence of sugar moiety, aglycon structure and microflora concentration on the human ileal hydrolysis of phenol glycosides, various quercetin and p-nitrophenol glycosides were incubated under anaerobic conditions (37 degrees C for 0, 0.5, 1, 2, 4, 6, 8, 10 and 24 h) with ileostomy fluids from three different donors. The glycosides, i.e. beta-D-glucopyranosides, beta-D-galactopyranosides, alpha-L-arabinofuranosides, beta-D-xylopyranosides and alpha-L-rhamnopyranosides as well as the liberated aglycones were identified by HPLC-DAD and HPLC-ESI-MS/MS. Among the quercetin glycosides under study, the 3-O-beta-D-glucopyranoside showed with 0.22 micromol/h the highest hydrolysis rate, followed by the 3-O-beta-D-galactopyranoside, the 3-O-beta-D-xylopyranoside and the 3-O-alpha-L-arabinofuranoside (0.04 and each 0.03 micromol/h, respectively). Quercetin 3-O-alpha-L-rhamnopyranoside was found to be stable for the entire incubation period. Using quercetin 3-O-beta-D-glucopyranoside as a representative example, linear hydrolysis rate was observed from 75 to 2500 microL ileostomy fluid corresponding to its microflora content (log 0.68 up to 21.9 colony forming units). Studies performed in the presence of antibiotics did not reveal any hydrolysis. The p-nitrophenol glycosides were hydrolyzed faster than the corresponding quercetin glycosides. The hydrolysis rate decreased from the beta-D-glucopyranoside (0.41 micromol/h), to the beta-D-galactopyranoside (0.21 micromol/h), the beta-D-xylopyranoside (0.12 micromol/h), the alpha-L-arabinofuranoside (0.09 micromol/h) to the alpha-L-rhamnopyranoside (0.06 micromol/h). These results demonstrate that the human ileal hydrolysis of phenol glycosides depends on the sugar and the aglycon structure as well as the microflora.

  17. Iridoid glycoside biosynthesis in Penstemon secundiflorus. Another H-5, H-9 trans iridoid glycoside

    DEFF Research Database (Denmark)

    Krull, Robert E.; Stermitz, Frank R.; Franzyk, Henrik

    1998-01-01

    Isolation and characterization of the new iridoid 10-hydroxy-(5 alpha H)-6-epidihydrocornin from Penstemon secundiflorus (Scrophulariaceae) is described. In biosynthetic experiments, deoxyloganic acid was incorporated into the transfused iridoid glycosides (5 alpha H)-6-epidihydrocornin and 10-hy......-hydroxy-(5 alpha H)-6-epidihydrocornin in P. secundiflorus. Formation of the trans-fused compounds is therefore a late event in the biosynthesis and does not occur during iridoid formation by cyclization of the open chain monoterpene precursor. In the same plant, 8-epideoxyloganic acid...... was not incorporated into the trans-iridoids. Deoxyloganic acid was also incorporated into 10-hydroxyhastatoside (which bears an 8 beta-methyl group), while 8-epideoxyloganic acid was incorporated into penstemoside (with an 8 alpha-methyl group). Thus, iridoid biosynthetic pathways leading from both deoxyloganic acid...

  18. A glycoside of Nicotina tabacum affects mouse dopaminergic behavior.

    Science.gov (United States)

    Masuda, Y; Ohnuma, S; Kawagoe, M; Sugiyama, T

    2003-01-01

    Climbing in the forced swimming test is considered a dopaminergic-specific behavior. A substance of Nicotina tabacum affecting dopamine neuronal activity was investigated using the mouse behavioral system. The substance was found to be a glycoside with the peripheral sugar chain structures Fuc alpha 1-2Gal, Gal beta 1-4GlcNAc and GalNAc alpha 1-3GalNAc and with basic polymannoses. The glycoside dose-dependently increased behavior via D2 neuronal activity, but not D1 activity. This suggests that smoking can affect human brain function not only via the nicotinic cholinergic neuron, but also via the D2 neuron.

  19. Three new steroid glycosides from the starfish Asterina pectinifera.

    Science.gov (United States)

    Li, Zhanqiang; Chen, Gang; Lu, Xuan; Wang, Haifeng; Feng, Baomin; Pei, Yuehu

    2013-10-01

    Three new steroid glycosides, pectiniosides H-J (1-3), were isolated along with three known compounds (4-6) including a steroid glycoside and two polyhydroxysteroids, from the alcoholic extract of the starfish Asterina pectinifera. The structures of 1-3 were determined by extensive NMR and HR-ESI-MS experiments. Compounds 1-4 did not show cytostatic activity on HL-60 cells below 100 μM, while compounds 5-6 showed moderate cytostatic activity, with IG50 values of 80.3 and 40.5 μM, respectively.

  20. Gas-phase reactivity of silver and copper coordinated monosaccharide cations studied by electrospray ionization and tandem mass spectrometry.

    Science.gov (United States)

    Boutreau, Laurence; Léon, Emmanuelle; Salpin, Jean-Yves; Amekraz, Badia; Moulin, Christophe; Tortajada, Jeanine

    2003-01-01

    The analytical distinction of the most common isomeric underivatized hexoses was investigated by means of mass spectrometry experiments. Electrospray ionization and tandem mass spectrometry were used in the analysis of silver and copper-coordinated monosaccharides (D-glucose, D-galactose, D-fructose, O-methyl-alpha-D-glucose and O-methyl-beta-D-glucose). The results show that cationization by Ag(+) allows the differentiation of the three first monosaccharides while the complexes formed by association of Cu(+) with these three monosacharides display a similar reactivity that prevents stereoisomer distinction. Unlike copper, silver adduct-ions of both alpha and beta anomeric O-methyl-D-glucoses exhibit specific decomposition patterns (i.e. a loss of methanol for the alpha-anomer and a loss of silver hydride for the beta-anomer), which allow an easy characterization. A theoretical survey of selected complexes, based on the use of DFT calculations were carried out on both anomers in order to rationalize the experimental findings.

  1. Three new aromatic glycosides from the ripe fruit of cherry tomato.

    Science.gov (United States)

    Ono, Masateru; Shiono, Yuki; Tanaka, Takayuki; Masuoka, Chikako; Yasuda, Shin; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

    2010-10-01

    Three new aromatic glycosides were isolated from the ripe fruit of cherry tomato [Lycopersicon esculentum var. cerasiforme (Dunal) Alef. (Solanaceae)] along with six known aromatic glycosides and one known steroidal alkaloid glycoside. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.

  2. Steviol glycosides in purified stevia leaf extract sharing the same metabolic fate.

    Science.gov (United States)

    Purkayastha, Sidd; Markosyan, Avetik; Prakash, Indra; Bhusari, Sachin; Pugh, George; Lynch, Barry; Roberts, Ashley

    2016-06-01

    The safety of steviol glycosides is based on data available on several individual steviol glycosides and on the terminal absorbed metabolite, steviol. Many more steviol glycosides have been identified, but are not yet included in regulatory assessments. Demonstration that these glycosides share the same metabolic fate would indicate applicability of the same regulatory paradigm. In vitro incubation assays with pooled human fecal homogenates, using rebaudiosides A, B, C, D, E, F and M, as well as steviolbioside and dulcoside A, at two concentrations over 24-48 h, were conducted to assess the metabolic fate of various steviol glycoside classes and to demonstrate that likely all steviol glycosides are metabolized to steviol. The data show that glycosidic side chains containing glucose, rhamnose, xylose, fructose and deoxy-glucose, including combinations of α(1-2), β-1, β(1-2), β(1-3), and β(1-6) linkages, were degraded to steviol mostly within 24 h. Given a common metabolite structure and a shared metabolic fate, safety data available for individual steviol glycosides can be used to support safety of purified steviol glycosides in general. Therefore, steviol glycosides specifications adopted by the regulatory authorities should include all steviol glycosides belonging to the five groups of steviol glycosides and a group acceptable daily intake established. Copyright © 2016 Elsevier Inc. All rights reserved.

  3. Rapid Determination of the Monosaccharide Composition and Contents in Tea Polysaccharides from Yingshuang Green Tea by Pre-Column Derivatization HPLC

    Directory of Open Access Journals (Sweden)

    Yujie Ai

    2016-01-01

    Full Text Available A pre-column derivatization high-performance liquid chromatography (HPLC method was developed and optimized to characterize and quantify the monosaccharides present in tea polysaccharides (TPS isolated from Yingshuang green tea. TPS sample was hydrolyzed with trifluoroacetic acid, subjected to pre-column derivatization using 1-phenyl-3-methyl-5-pyrazolone (PMP, and separated on an Agilent TC-C18 column (4.6 mm × 250 mm, 5 μm with UV detection at 250 nm. A mixture of ten PMP derivatives of standard monosaccharides (mannose, ribose, rhamnose, glucuronic acid, galacturonic acid, glucose, xylose, galactose, arabinose, and fucose could be baseline separated within 20 min. Moreover, quantitative analysis of the component monosaccharides in Yingshuang green tea TPS was achieved, indicating the TPS consisted of mannose, ribose, rhamnose, glucuronic acid, galacturonic acid, glucose, xylose, galactose, and arabinose in the molar contents of 0.72, 0.78, 0.89, 0.13, 0.15, 0.36, 0.39, 0.36, 0.36, and 0.38 μM, respectively. Recovery efficiency for component monosaccharides from TPS ranged from 93.6 to 102.4% with RSD values lower than 2.5%. In conclusion, pre-column derivatization HPLC provides a rapid, reproducible, accurate, and quantitative method for analysis of the monosaccharide composition and contents in TPS, which may help to further explore the relationship between TPS monosaccharides isolated from different tea varieties and their biological activity.

  4. Cytotoxicity of natural ginseng glycosides and semisynthetic analogues

    NARCIS (Netherlands)

    Atopkina, LN; Malinovskaya, GV; Elyakov, GB; Uvarova, NI; Woerdenbag, HJ; Koulman, A; Potier, P

    The cytotoxicity of natural glycosides from Ginseng, semisynthetic analogues and related triterpenes of the dammarane series, isolated from the leaves of the Far-East species of the genus Betula was studied in order to elucidate structure-activity relationships. Some of the compounds studied were

  5. A new phenolic glycoside from the stem of Dendrobium nobile.

    Science.gov (United States)

    Zhou, Xue-Ming; Zheng, Cai-Juan; Wu, Jia-Ting; Chen, Guang-Ying; Zhang, Bin; Sun, Chong-Ge

    2017-05-01

    A new phenolic glycoside dendroside (1), together with seven known compounds (2-8) were isolated from the stems of Dendrobium nobile. The structures of these compounds were elucidated using comprehensive spectroscopic methods. The inhibitory activities of all compounds against three cancer cell lines HeLa, MCF-7 and A549 were evaluated.

  6. Two aurone glycosides from heartwood of Pterocarpus santalinus.

    Science.gov (United States)

    Kesari, Achyut Narayan; Gupta, Rajesh Kumar; Watal, Geeta

    2004-12-01

    Two new aurone glycosides, 6 hydroxy 5 methyl 3',4',5' trimethoxy aurone 4-O-alpha-L-rhamnopyranoside and 6,4' dihydroxy aurone 4-O-rutinoside have been isolated from the ethanolic extract of the wood of Pterocarpus santalinus. Their structures were determined on the basis of chemical and spectroscopic analysis (UV, IR, EIMS, (1)H and (13)C NMR).

  7. Soulieoside R : A New Cycloartane Triterpenoid Glycoside from Souliea vaginata

    Directory of Open Access Journals (Sweden)

    Qiongyu Zou

    2018-01-01

    Full Text Available A new cycloartane triterpenoid glycoside, named soulieoside R, was isolated from the rhizomes of Souliea vaginata. Its structure was characterized by comprehensive analyses of 1H, 13C NMR, COSY, HSQC, HMBC, NOESY spectroscopic, and HRESIMS mass spectrometric data, as well as chemical methods. The new compound showed weak inhibitory activity against three human cancer cell lines.

  8. Antioxidative flavan-3-ol glycosides from stems of Rhizophora stylosa.

    Science.gov (United States)

    Takara, Kensaku; Kuniyoshi, Ayako; Wada, Koji; Kinjyo, Kazuhiko; Iwasaki, Hironori

    2008-08-01

    Two flavan-3-ol glycosides together with seven flavan-3-ols were isolated from stems of the mangrove plant, Rhizophora stylosa. Their structures were established as glabraoside A (7) and glabraoside B (8) by spectroscopic and chemical methods. The antioxidative activity of these isolated compounds evaluated by the diphenylpicrylhydrazyl (DPPH) radical scavenging reaction was higher than that of L-ascorbic acid.

  9. Chevalierinoside A: A new isoflavonoid glycoside from the stem bark ...

    African Journals Online (AJOL)

    Chevalierinoside A (1), a new isoflavonoid glycoside determined as biochanin A 7-O-[a-L-rhamnopyranosyl-1→6-β-D-apiofuranosyl-1→2-β-D-glucopyranoside], together with the known friedelin (2), friedelan-3b-ol (3) and betulinic acid (4), were isolated from the stem bark of Antidesma chevalieri Beille. Their structures ...

  10. Cycloartane-type glycosides from two species of Astragalus (Fabaceae).

    Science.gov (United States)

    Linnek, Jens; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Duchamp, Olivier; Mirjolet, Jean-François; Lacaille-Dubois, Marie-Aleth

    2009-04-01

    Three known cycloartane-type glycosides were isolated from the roots of two different species of Astragalus, A. glycyphyllos, A. sempervirens. The identification of these compounds were mainly achieved by 2D NMR spectroscopic techniques and FAB-MS. The results of our studies confirm that triterpene saponins from the cycloartane-type skeleton might be chemotaxonomically significant to the genus Astragalus.

  11. [Pharmacological properties od steroid glycosides from Ruscus ponticus].

    Science.gov (United States)

    Abuladze, G V; Mulkidzhanian, K G; Novikova, Zh N

    2002-01-01

    Some pharmacological properties of the sum of steroidal glycosides (ruscoponin preparation) extracted from underground parts of Ruscus ponticus were studied. The drug exhibits a pronounced antiexudative effect (related to the alpha 1-adrenergic activity) on the models of formalin edema and pouch granuloma in rats and a thermal rectum inflammation in mice. The drug exhibited no hepato-, nephro-, and gastrotoxicity.

  12. Effects of Triptergium Glycosides on Expressions of MCP- 1 and ...

    African Journals Online (AJOL)

    Effects of Triptergium Glycosides on Expressions of MCP- 1 and CTGF in Rats with Early Diabetic Nephropathy. Ji-Qiang Zhang, Yan Zhang, Xiao-Li Yin, Ping Yang, Hai-Feng Zhang, Ya-Ling Guo, Wei-Dong Chen ...

  13. Flavonol glycosides from distilled petals of Rosa damascena Mill.

    Science.gov (United States)

    Schiber, Andreas; Mihalev, Kiril; Berardini, Nicolai; Mollov, Plamen; Carle, Reinhold

    2005-01-01

    Flavonol glycosides were extracted from petals of Rosa damascena Mill. after industrial distillation for essential oil recovery and characterized by high-performance liquid chromatography-electrospray ionization mass spectrometry. Among the 22 major compounds analyzed, only kaempferol and quercetin glycosides were detected. To the best of our knowledge, the presence of quercetin 3-O-galactoside and quercetin 3-O-xyloside has so far not been reported within the genus Rosa. In addition, based on their fragmentation patterns, several acylated quercetin and kaempferol glycosides, some of them being disaccharides, were identified for the first time. The kaempferol glycosides, along with the kaempferol aglycone, accounted for 80% of the total compounds that were quantified, with kaempferol 3-O-glucoside being the predominant component. The high flavonol content of approximately 16 g/kg on a dry weight basis revealed that distilled rose petals represent a promising source of phenolic compounds which might be used as functional food ingredients, as natural antioxidants or as color enhancers.

  14. Hydrolytical instability of hydroxyanthraquinone glycosides in pressurized liquid extraction.

    Science.gov (United States)

    Wianowska, Dorota

    2014-05-01

    Hydroxyanthraquinones represent a group of pharmacologically active compounds characteristic for plants of the Rumex and Rheum genera. These compounds in the human intestine act as laxative compounds. As they cause the greatest side effects and are often abused by the public, their accurate analysis in plants and plant-derived laxatives is much needed. To isolate compounds from plants, pressurized liquid extraction (PLE) is frequently applied. The technique has been regarded, so far, as very effective, even in isolation of sensitive compounds for which exposure time in high temperature has a negative impact. This work demonstrates some interesting and surprising results accompanying PLE of hydroxyanthraquinones from the Rumex crispus L. root using methanol/water mixtures as extractant. The presented results demonstrate that glycoside forms of hydroxyanthraquinones (emodin-8-O-β-D-glucopyranoside, chrysophanol-8-O-β-D-glucopyranoside, and physcion-8-O-β-D-glucopyranoside) are hydrolytically unstable even in the short-lasting PLE. The increase of water concentration in the extractant leads to the increase of the transformation degree of the glycoside forms to the corresponding aglycones (emodin, chrysophanol, and physcion), increasing the concentration of the latter. The rise in the PLE temperature accelerates the hydrolytical degradation of the glycoside forms. The extension of the extraction time also intensifies this process. The presented results show that extraction of glycosides using extractants containing water can lead to false conclusions about the chemical composition of plants.

  15. Glycosidation of Methanol with Ribose: An Interdisciplinary Undergraduate Laboratory Experiment

    Science.gov (United States)

    Simon, Erin; Cook, Katie; Pritchard, Meredith R.; Stripe, Wayne; Bruch, Martha; Bendinskas, Kestutis

    2010-01-01

    This exercise provides students hands-on experience with the topics of glycosidation, hemiacetal and acetal formation, proton nuclear magnetic resonance ([superscript 1]H NMR) spectroscopy, and kinetic and thermodynamic product formation. In this laboratory experiment, the methyl acetal of ribose is synthesized, and the kinetic and thermodynamic…

  16. Bottom-up elucidation of glycosidic bond stereochemistry

    DEFF Research Database (Denmark)

    Gray, Christopher J.; Schindler, Baptiste; Migas, Lukasz G.

    2017-01-01

    a particular challenge. Here, we show that "memory" of anomeric configuration is retained following gas-phase glycosidic bond fragmentation during tandem mass spectrometry (MS(2)). These findings allow for integration of MS(2) with ion mobility spectrometry (IM-MS(2)) and lead to a strategy to distinguish α...

  17. Diverse modes of galacto-specific carbohydrate recognition by a family 31 glycoside hydrolase from Clostridium perfringens.

    Directory of Open Access Journals (Sweden)

    Julie M Grondin

    Full Text Available Clostridium perfringens is a commensal member of the human gut microbiome and an opportunistic pathogen whose genome encodes a suite of putative large, multi-modular carbohydrate-active enzymes that appears to play a role in the interaction of the bacterium with mucin-based carbohydrates. Among the most complex of these is an enzyme that contains a presumed catalytic module belonging to glycoside hydrolase family 31 (GH31. This large enzyme, which based on its possession of a GH31 module is a predicted α-glucosidase, contains a variety of non-catalytic ancillary modules, including three CBM32 modules that to date have not been characterized. NMR-based experiments demonstrated a preference of each module for galacto-configured sugars, including the ability of all three CBM32s to recognize the common mucin monosaccharide GalNAc. X-ray crystal structures of the CpGH31 CBM32s, both in apo form and bound to GalNAc, revealed the finely-tuned molecular strategies employed by these sequentially variable CBM32s in coordinating a common ligand. The data highlight that sequence similarities to previously characterized CBMs alone are insufficient for identifying the molecular mechanism of ligand binding by individual CBMs. Furthermore, the overlapping ligand binding profiles of the three CBMs provide a fail-safe mechanism for the recognition of GalNAc among the dense eukaryotic carbohydrate networks of the colonic mucosa. These findings expand our understanding of ligand targeting by large, multi-modular carbohydrate-active enzymes, and offer unique insights into of the expanding ligand-binding preferences and binding site topologies observed in CBM32s.

  18. [Malabsorption of fermentable oligo-, di-, or monosaccharides and polyols (FODMAP) as a common cause of unclear abdominal discomfort].

    Science.gov (United States)

    Goebel-Stengel, M; Mönnikes, H

    2014-06-01

    Carbohydrate malabsorption is a frequent but underestimated cause of unexplained gastrointestinal symptoms like meteorism, flatulence, pain and diarrhea. By means of hydrogen and/or methane breath test after ingestion of the respective carbohydrate it can be identified and diagnosed easily, fast and reliably by successful nutritional therapy. Besides the well known complaints caused by lactose and fructose malabsorption, other fermentable oligo-, di-, or monosaccharides and polyols (akronym: FODMAP) can cause abdominal discomfort and IBS-like symptoms. In addition to lactose (dairy products) and fructose (apples, pears, mango, watermelon), FODMAPs comprise galactans (legumes), fructans (wheat, onions, garlic, artichoke) and the artificial sweeteners sorbitol, mannitol, maltitol and xylitol (sugar free candy, light products). A general restriction of all FODMAP components can be beneficial in relieving symptoms and improving quality of life in patients with functional gastrointestinal complaints. © Georg Thieme Verlag KG Stuttgart · New York.

  19. Characterizing harmful advanced glycation end-products (AGEs) and ribosylated aggregates of yellow mustard seed phytocystatin: Effects of different monosaccharides

    Science.gov (United States)

    Ahmed, Azaj; Shamsi, Anas; Bano, Bilqees

    2017-01-01

    Advanced glycation end products (AGEs) are at the core of variety of diseases ranging from diabetes to renal failure and hence gaining wide consideration. This study was aimed at characterizing the AGEs of phytocystatin isolated from mustard seeds (YMP) when incubated with different monosaccharides (glucose, ribose and mannose) using fluorescence, ultraviolet, circular dichroism (CD) spectroscopy and microscopy. Ribose was found to be the most potent glycating agent as evident by AGEs specific fluorescence and absorbance. YMP exists as a molten globule like structure on day 24 as depicted by high ANS fluorescence and altered intrinsic fluorescence. Glycated YMP as AGEs and ribose induced aggregates were observed at day 28 and 32 respectively. In our study we have also examined the anti-aggregative potential of polyphenol, resveratrol. Our results suggested the anti-aggregative behavior of resveratrol as it prevented the in vitro aggregation of YMP, although further studies are required to decode the mechanism by which resveratrol prevents the aggregation.

  20. Interactive effect of brassinosteroids and cytokinins on growth, chlorophyll, monosaccharide and protein content in the green alga Chlorella vulgaris (Trebouxiophyceae).

    Science.gov (United States)

    Bajguz, Andrzej; Piotrowska-Niczyporuk, Alicja

    2014-07-01

    Interaction between brassinosteroids (BRs) (brassinolide, BL; 24-epibrassinolide, 24-epiBL; 28-homobrassinolide, 28-homoBL; castasterone, CS; 24-epicastasterone, 24-epiCS; 28-homocastasterone, 28-homoCS) and adenine- (trans-zeatin, tZ; kinetin, Kin) as well as phenylurea-type (1,3-diphenylurea, DPU) cytokinins (CKs) in the regulation of cell number, phytohormone level and the content of chlorophyll, monosaccharide and protein in unicellular green alga Chlorella vulgaris (Trebouxiophyceae) were examined. Chlorella vulgaris exhibited sensitivity to CKs in the following order of their stimulating properties: 10 nM tZ > 100 nM Kin >1 μM DPU. Exogenously applied BRs possessed the highest biological activity in algal cells at concentration of 10 nM. Among the BRs, BL was characterized by the highest activity, while 28-homoCS - by the lowest. The considerable increase in the level of all endogenous BRs by 27-46% was observed in C. vulgaris culture treated with exogenous 10 nM tZ. It can be speculated that CKs may stimulate BR activity in C. vulgaris by inducing the accumulation of endogenous BRs. CKs interacted synergistically with BRs increasing the number of cells and endogenous accumulation of proteins, chlorophylls and monosaccharides in C. vulgaris. The highest stimulation of algal growth and the contents of analyzed biochemical parameters were observed for BL applied in combination with tZ, whereas the lowest in the culture treated with both 28-homoCS and DPU. However, regardless of the applied mixture of BRs with CKs, the considerable increase in cell number and the metabolite accumulation was found above the level obtained in cultures treated with any single phytohormone in unicellular green alga C. vulgaris. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  1. Characterization of β-N-acetylhexosaminidase (LeHex20A), a member of glycoside hydrolase family 20, from Lentinula edodes (shiitake mushroom).

    Science.gov (United States)

    Konno, Naotake; Takahashi, Hideyuki; Nakajima, Masahiro; Takeda, Takumi; Sakamoto, Yuichi

    2012-06-01

    We purified and cloned a β-N-acetylhexosaminidase, LeHex20A, with a molecular mass of 79 kDa from the fruiting body of Lentinula edodes (shiitake mushroom). The gene lehex20a gene had 1,659 nucleotides, encoding 553 amino acid residues. Sequence analysis indicated that LeHex20A belongs to glycoside hydrolase (GH) family 20, and homologues of lehex20a are broadly represented in the genomes of basidiomycetes. Purified LeHex20A hydrolyzed the terminal monosaccharide residues of β-N-acetylgalactosaminides and β-N-acetylglucosaminides, indicating that LeHex20A is a β-N-acetylhexosaminidase classified into EC 3.2.1.52. The maximum LeHex20A activity was observed at pH 4.0 and 50°C. The kinetic constants were estimated using chitooligosaccharides with degree of polymerization 2-6. GH20 β-N-acetylhexosaminidases generally prefer chitobiose among natural substrates. However, LeHex20A had the highest catalytic efficiency (kcat/Km) for chitotetraose, and the Km values for GlcNAc6 were 3.9-fold lower than for chitobiose. Furthermore, the enzyme partially hydrolyzed amorphous chitin polymers. These results indicate that LeHex20A can produce N-acetylglucosamine from long-chain chitomaterials.

  2. Determining the monosaccharides of the sea urchin (Paracentrotus lividus) coelomocytes via the CapLC-ESI-MS/MS system and the lectin histochemistry.

    Science.gov (United States)

    Şener, Ecem; Deveci, Remziye

    2015-01-01

    The essential mechanism within immune systems is the recognition of pathogens and parasites by the immune system cells, which attach to their targets and destroy them. Glycans are fundamental macromolecular components of all cells, and are important in the vertebrate immunity. But, glycans have been investigated rarely in coelomocytes of echinoids. Hence, the aim of this study is to determine the monosaccharides which form glycan chains on the sea urchin immune system cells, coelomocytes, via analytical and lectin histochemistry methods. The study material is the coelomocytes obtained from adult sea urchin Paracentrotus lividus. In order to analyze the monosaccharides with the Capillary Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry (CapLC-ESI-MS/MS) system, the samples underwent hydrolysation, reacetylation and derivatization steps. In order to determine the monosaccharides with the lectin histochemistry, the cells were incubated with fluorescein isothiocyanate (FITC) conjugated PNA, HPA, WGA-suc, WGA, and PSL lectins and then photographed with the fluorescence microscope. As a result of the CapLC-ESI-MS/MS analysis; mannose, ribose, N-acetylglucosamine, glucose, N-acetylgalactosamine, galactose, arabinose, xylose and fucose monosaccharides were detected. A peak area calculation analysis revealed the most prevalent saccharides as glucose, galactose and fucose, respectively. Lectin histochemistry came out with higher intensity emission signals obtained from the FITC-conjugated lectin WGA, which is specific to N-acetylglucosamine and sialic acid in comparison to the emission obtained from the sialic acid unspecific WGA-suc lectin. This finding indicates the existence of sialic acid within coelomocytes. Fluorescent emissions from other lectins were detected at lower levels. Determination of the monosaccharides which form glycan chains of the sea urchin coelomocytes and elucidating their similarities among other invertebrate and vertebrate

  3. Antioxidative phenylethanoid and phenolic glycosides from Picrorhiza scrophulariiflora.

    Science.gov (United States)

    Wang, Hao; Sun, Yang; Ye, Wen-Cai; Xiong, Fei; Wu, Jia-Jun; Yang, Chun-Hua; Zhao, Shou-Xun

    2004-05-01

    One new phenylenthanoid glycoside, scroside D (2), was isolated from the roots of Picrorhiza scrophulariiflora (Scrophulariaceae), together with nine known phenylethanoid and phenolic glycosides: 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside (1), 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranoside (3), scroside B (4), hemiphroside A (5), plantainoside D (6), scroside A (7), androsin (8), piceoside (9), and 6-O-feruloyl-beta-D-glucopyranoside (10). The structures of these compounds were elucidated using spectroscopic methods. The antioxidative activities of these isolated compounds were evaluated based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. Compounds 1, 2, and 6 showed potent antioxidative effects as those of ascorbic acid and the structure-activity relationship is discussed.

  4. Structures of the novel diterpene glycosides from Stevia rebaudiana.

    Science.gov (United States)

    Chaturvedula, Venkata Sai Prakash; Prakash, Indra

    2011-06-01

    From the commercial extract of the leaves of Stevia rebaudiana, two new diterpenoid glycosides were isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside, and dulcoside A. The structures of the two new compounds were identified as 13-[(2-O-6-deoxy-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (1), and 13-[(2-O-6-deoxy-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (2), on the basis of extensive NMR and MS spectral data as well as chemical studies. Copyright © 2011 Elsevier Ltd. All rights reserved.

  5. Beaming steviol glycoside analysis into the next dimension.

    Science.gov (United States)

    Zimmermann, Benno F

    2018-02-15

    Nine state-of-the-art reversed phase (RP) columns for ultra-high performance liquid chromatography were tested for the separation of steviol glycosides. The main criteria were resolution of the critical peak pair rebaudioside A and stevioside and the retention time of rebaudioside D. Three columns yielded a resolution of 2 or more of the critical peak pair and two of them showed sufficient retention of rebaudioside D, namely 1.62 and 1.84min corresponding to retention factors of 0.98 and 1.24. The separation of nine steviol glycosides was possible in 11min with UV and MS compatible, buffer-free eluents at moderate temperature. The presented method is proposed to be adopted as a new official method. Copyright © 2017 Elsevier Ltd. All rights reserved.

  6. New terpenoid glycosides obtained from Rosmarinus officinalis L. aerial parts.

    Science.gov (United States)

    Zhang, Yi; Adelakun, Tiwalade Adegoke; Qu, Lu; Li, Xiaoxia; Li, Jian; Han, Lifeng; Wang, Tao

    2014-12-01

    Five new terpenoid glycosides, named as officinoterpenosides A₁ (1), A₂ (2), B (3), C (4), and D (5), together with 11 known ones, (1S,4S,5S)-5-exo-hydrocamphor 5-O-β-D-glucopyranoside (6), isorosmanol (7), rosmanol (8), 7-methoxyrosmanol (9), epirosmanol (10), ursolic acid (11), micromeric acid (12), oleanolic acid (13), niga-ichigoside F₁ (14), glucosyl tormentate (15), and asteryunnanoside B (16), were obtained from the aerial parts of Rosmarinus officinalis L. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D and 2D NMR). Among the new ones, 1 and 2, 3 and 4 are diterpenoid and triterpenoid glycosides, respectively; and 5 is a normonoterpenoid. For the known ones, 6 was isolated from the Rosmarinus genus first, and 15, 16 were obtained from this species for the first time. Copyright © 2014 Elsevier B.V. All rights reserved.

  7. Investigations of Reactive Carbohydrates in Glycosidic Bond Formation and Degradation

    DEFF Research Database (Denmark)

    Heuckendorff, Mads

    was to develop new synthetic methods to evolve the field of synthetic carbohydrate chemistry. In addition, easy methods for obtaining complex oligosaccharides are needed to accommodate biochemical research and drug development. Furthermore, the aim was to shed light on the complex mechanisms of glycosylation...... and hy rolysis of glycosides. This mechanistic insight can then be used to develop new synthetic methods and obtain a better understanding of already existing methods. In Chapter 1 general aspects of synthetic carbohydrate chemistry is described with an emphasis on elements that affects reactivity...... and their properties in glycosylations were carefully examined. The physical chemistry aspects of conformationally changed donors were investigated with emphasis on the anomeric effect. Finally, neighboring group effects in glycosylations and hydrolysis of glycosides were investigated. The goal of this research...

  8. A New Flavone C-Glycoside from Clematis rehderiana

    Directory of Open Access Journals (Sweden)

    Zhi-Zhi Du

    2010-01-01

    Full Text Available A new flavone C-glycoside, isovitexin 6″-O-E-p-coumarate (1 and two known flavonoid glycosides—quercetin 3-O-β-D-glucuronopyranoside (2 and isoorientin (3—were isolated from an ethanol extract of aerial parts of Clematis rehderiana. Their structures were determined by spectroscopic methods. The antioxidant effects of the two flavone C-glycosides were evaluated by both the MTT and DPPH assays. Compound 1 showed potent activities against H2O2-induced impairment in PC12 cells within the concentration range tested, whereas compound 3 scavenged DPPH radical strongly, with an IC50 value of 13.5 μM.

  9. Antioxidative flavonol glycosides from the flowers of Abelmouschus manihot.

    Science.gov (United States)

    Zhang, Yi; He, Wei; Li, Chunmei; Chen, Qiu; Han, Lifeng; Liu, Erwei; Wang, Tao

    2013-01-01

    Bioassay-guided fractionation led to the isolation of six new flavonol glycosides, floramanosides A (1), B (2), C (3), D (4), E (5), and F (6), from the flowers of Abelmouschus manihot. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D- and 2D-NMR). Activity screening results showed that the compounds had 2,2-diphenyl-1-picrylhydrazyl scavenging and aldose reductase inhibitory activities.

  10. New secoiridoid Glycosides from the Roots of Picrorhiza Scrophulariiflora

    OpenAIRE

    Zou, Lian-Chun; Zhu, Tong-Fei; Xiang, Hua; Yu, Lu; Yan, Zhi-Hui; Gan, Shu-Cai; Wang, Da-Cheng; Zeng, Sheng; Deng, Xu-Ming

    2008-01-01

    Three new secoiridoid glycosides, named picrogentiosides A (1), B (2) and C (3), have been isolated from the underground parts of Picrorhiza Scrophulariiflora, together with the two known compounds plantamajoside (4) and plantainoside D (5). Their structures were established by spectroscopic analyses and comparisons with data from related compounds. A pilot pharmacological study showed that picrogentiosides A (1) and B (2) have an immunomodulatory effect in vitro.

  11. New secoiridoid Glycosides from the Roots of Picrorhiza Scrophulariiflora

    Directory of Open Access Journals (Sweden)

    Xu-Ming Deng

    2008-09-01

    Full Text Available Three new secoiridoid glycosides, named picrogentiosides A (1, B (2 and C (3, have been isolated from the underground parts of Picrorhiza Scrophulariiflora, together with the two known compounds plantamajoside (4 and plantainoside D (5. Their structures were established by spectroscopic analyses and comparisons with data from related compounds. A pilot pharmacological study showed that picrogentiosides A (1 and B (2 have an immunomodulatory effect in vitro.

  12. New secoiridoid glycosides from the roots of Picrorhiza scrophulariiflora.

    Science.gov (United States)

    Zou, Lian-Chun; Zhu, Tong-Fei; Xiang, Hua; Yu, Lu; Yan, Zhi-Hui; Gan, Shu-Cai; Wang, Da-Cheng; Zeng, Sheng; Deng, Xu-Ming

    2008-09-01

    Three new secoiridoid glycosides, named picrogentiosides A (1), B (2) and C (3), have been isolated from the underground parts of Picrorhiza Scrophulariiflora, together with the two known compounds plantamajoside (4) and plantainoside D (5). Their structures were established by spectroscopic analyses and comparisons with data from related compounds. A pilot pharmacological study showed that picrogentiosides A (1) and B (2) have an immunomodulatory effect in vitro.

  13. A new cycloartane triterpenoid glycoside from Souliea vaginata.

    Science.gov (United States)

    Wu, Hai-Feng; Liu, Xin; Zhu, Yin-Di; Zhou, Jing; Gong, Ying-Ying; Ma, Guo-Xu; Xu, Xu-Dong; Liu, Yi-Lin; Luo, Zheng-Hong; Chen, Di-Zhao; Zou, Qiong-Yu; Zhao, Zi-Jian

    2017-11-01

    One new cycloartane triterpenoid glycoside, soulieoside Q (1), together with four known compounds (2-5) were isolated from the ethanolic extract of the rhizomes of Souliea vaginata Maxim. The structure of the new compound was determined by extensive spectroscopic analysis including 1D and 2D NMR and HRESIMS, as well as chemical methods. Compound 1 was evaluated for its cytotoxic activities against HepG2 and A549 cancer cell lines.

  14. Soulieoside O, a new cyclolanostane triterpenoid glycoside from Souliea vaginata.

    Science.gov (United States)

    Wu, Hai-Feng; Li, Peng-Fei; Zhu, Yin-Di; Zhang, Xiao-Po; Ma, Guo-Xu; Xu, Xu-Dong; Liu, Yi-Lin; Luo, Zheng-Hong; Chen, Di-Zhao; Zou, Qiong-Yu; Zhao, Zi-Jian

    2017-12-01

    A new cyclolanostane triterpenoid glycoside, soulieoside O (1), together with 25-O-acetylcimigenol-3-O-β-d-xylopyranoside (2) and cimigenol-3-O-β-d-xylopyranoside (3), was isolated from the rhizomes of Souliea vaginata. Their structures were characterized by spectroscopic analysis and chemical methods. The new compound showed moderate inhibitory activity against three human cancer cell lines with IC 50 values of 9.3-22.5 μM.

  15. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives

    OpenAIRE

    Pandey, Ramesh Prasad; Parajuli, Prakash; Shin, Ju Yong; Lee, Jisun; Lee, Seul; Hong, Young-Soo; Park, Yong Il; Kim, Joong Su; Sohng, Jae Kyung

    2014-01-01

    A UDP glucosyltransferase from Bacillus licheniformis was overexpressed, purified, and incubated with nucleotide diphosphate (NDP) d- and l-sugars to produce glucose, galactose, 2-deoxyglucose, viosamine, rhamnose, and fucose sugar-conjugated resveratrol glycosides. Significantly higher (90%) bioconversion of resveratrol was achieved with α-d-glucose as the sugar donor to produce four different glucosides of resveratrol: resveratrol 3-O-β-d-glucoside, resveratrol 4′-O-β-d-glucoside, resveratr...

  16. A Chalcone Glycoside from the Fruits of Sorbus commixta Hedl.

    Directory of Open Access Journals (Sweden)

    Kyu Yun Chai

    2009-12-01

    Full Text Available Sorbus commixta Hedl. (Rosaceae has been traditionally used in oriental countries for the treatment of asthma and other bronchial disorders. In this study, a chalcone glycoside was isolated from the ethyl acetate extract of the fruits of this plant. The compound was identified as neosakuranin based on the spectroscopic analysis and comparion with literature data. This is the first report of isolation of neosakuranin from Sorbus commixta.

  17. Two new geranylphenylacetate glycosides from the barks of Cinnamomum cassia.

    Science.gov (United States)

    Zeng, Jun-Fen; Zhu, Hu-Cheng; Lu, Jian-Wu; Hu, Lin-Zhen; Song, Jin-Chun; Zhang, Yong-Hui

    2017-08-01

    Two new glycosides, cinnacassides F (1) and G (2), with a rare geranylphenylacetate carbon skeleton, were isolated from the barks of Cinnamomum cassia, along with three known analogues, cinnacassides A (3), B (4) and C (5). The structures of the new compounds were elucidated on the basis of extensive NMR spectroscopic analyses and chemical method. Compounds 1-5 were investigated for their immunomodulatory activities, and compounds 1, 3 and 4 showed differential immunosuppressive activities against murine lymphocytes.

  18. [A new chromone glycoside from roots of Polygonum multiflorum].

    Science.gov (United States)

    Zhao, Hui-Nan; Chen, Li-Li; Huang, Xiao-Jun; Wang, Ying; Li, Yao-Lan; Ye, Wen-Cai

    2014-04-01

    Several kinds of column chromatography methods were used to investigate the chemical constituents of roots of Polygonum multiflorum. The structures of the isolated compounds were identified based on their physicochemical properties, spectral data and chemical methods. A new chromone glycoside was isolated and its structure was identified as (S)-2-(2'-hydroxypropyl)-5-methyl7-hydroxychromone-7-0-alpha-L-fucopyranosyl (1-->2)-beta-D-glucopyranoside (1).

  19. Isocartormin, a novel quinochalcone C-glycoside from Carthamus tinctorius

    Directory of Open Access Journals (Sweden)

    Feng Li

    2017-07-01

    Full Text Available A new semi-quinonechalcone C-glycoside isocartormin along with cartormin and safflomin C were isolated from the water extract of Carthamus tinctorius L. The structure of isocartormin was determined by extensive analysis of HR-MS, 1D- and 2D NMR data, and by comparison with those of cartormin reported previously by our group. Isocartormin was identified as a diastereoisomer of cartormin with a reverse configuration at C-18.

  20. Acylated flavonol glycosides from the forage legume, Onobrychis viciifolia (sainfoin).

    Science.gov (United States)

    Veitch, Nigel C; Regos, Ionela; Kite, Geoffrey C; Treutter, Dieter

    2011-04-01

    Ten acylated flavonol glycosides were isolated from aqueous acetone extracts of the aerial parts of the forage legume, Onobrychis viciifolia, and their structures determined using spectroscopic methods. Among these were eight previously unreported examples which comprised either feruloylated or sinapoylated derivatives of 3-O-di- and 3-O-triglycosides of kaempferol (3,5,7,4'-tetrahydroxyflavone) or quercetin (3,5,7,3',4'-pentahydroxyflavone). The diglycosides were acylated at the primary Glc residue of O-α-Rhap(1→6)-β-Glcp (rutinose), whereas the triglycosides were acylated at the terminal Rha residues of the branched trisaccharides, O-α-Rhap(1→2)[α-Rhap(1→6)]-β-Galp or O-α-Rhap(1→2)[α-Rhap(1→6)]-β-Glcp. Identification of the primary 3-O-linked hexose residues as either Gal or Glc was carried out by negative ion electrospray and serial MS, and cryoprobe NMR spectroscopy. Analysis of UV and MS spectra of the acylated flavonol glycosides provided additional diagnostic features relevant to direct characterisation of these compounds in hyphenated analyses. Quantitative analysis of the acylated flavonol glycosides present in different aerial parts of sainfoin revealed that the highest concentrations were in mature leaflets. Copyright © 2011 Elsevier Ltd. All rights reserved.

  1. Identification of a flavonoid C-glycoside as potent antioxidant.

    Science.gov (United States)

    Wen, Lingrong; Zhao, Yupeng; Jiang, Yueming; Yu, Limei; Zeng, Xiaofang; Yang, Jiali; Tian, Miaomiao; Liu, Huiling; Yang, Bao

    2017-09-01

    Flavonoids have been documented to have good antioxidant activities in vitro. However, reports on the cellular antioxidant activities of flavonoid C-glycosides are very limited. In this work, an apigenin C-glycoside was purified from Artocarpus heterophyllus by column chromatography and was identified to be 2″-O-β-D-xylosylvitexin by nuclear magnetic resonance spectroscopy. The cellular antioxidant activity and anticancer activity of 2″-O-β-D-xylosylvitexin were evaluated for the first time. The quantitative structure-activity relationship was analysed by molecular modeling. Apigenin presented an unexpected cellular antioxidation behaviour. It had an antioxidant activity at low concentration and a prooxidant activity at high concentration, whereas 2″-O-β-D-xylosylvitexin showed a dose-dependent cellular antioxidant activity. It indicated that C-glycosidation improved the cellular antioxidation performance of apigenin and eliminated the prooxidant effect. The ortho-dihydroxyl at C-3'/C-4' and C-3 hydroxyl in the flavonoid skeleton play important roles in the antioxidation behaviour. The cell proliferation assay revealed a low cytotoxicity of 2″-O-β-D-xylosylvitexin. Copyright © 2017 Elsevier Inc. All rights reserved.

  2. NMR Characterization of Flavanone Naringenin 7-O-Glycoside Diastereomer

    Directory of Open Access Journals (Sweden)

    SUN Li-juan

    2017-12-01

    Full Text Available To discriminate R and S flavanone glycoside using NMR, the mixture of R and S naringenin 7-O-glycoside was first isolated from Gleditsia sinensis. 1H and 13C NMR data of the mixture were recorded with 1H NMR, 13C NMR, 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC in DMSO-d6 solution. The two diastereomers were then separated with chiral chromatographic isolation, with their absolute configurations determined by circular dichroism. To avoid the disturbance of protons from glucose residues to dihydroflavonoid, 1H NMR spectra were acquired for pure R and S naringenin 7-O-glycoside and their mixture in CD3CN. The two diastereomers showed the largest proton chemical shift differences at the end group of glucose residue (H-1" with a chemical shift difference of 9.4 Hz. The OH-5 proton showed a chemical shift difference of 5.8 Hz. The chemical shift of the three protons on ring C were all influenced by configuration.

  3. C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity

    Directory of Open Access Journals (Sweden)

    Aleksandra Rusin

    2013-01-01

    Full Text Available This paper presents our attempt to investigate scopes and the limitations of olefin cross-metathesis (CM reaction in the synthesis of complex C-glycosides of genistein and evaluation of their antiproliferative activities. Novel genistein glycoconjugates were synthesized with the utility of CM reaction initiated by first and second generation of Grubbs catalysts. The relative reactivity of utilized olefins, based on categories proposed by Grubbs, was estimated. In vitro experiments in cancer cell lines showed that the selected derivatives (3a and 3f exhibited higher antiproliferative potential than the parent compound, genistein, and were able to block the cell cycle in the G2/M phase. The observed mechanism of action of C-glycosidic derivatives was similar to the activity of their O-glycosidic counterparts. These compounds were stable in culture medium. The obtained results show that our approach to genistein modification with application of cross-metathesis reaction allowed to obtain stable glycoconjugates with improved anticancer potential, compared to the parent isoflavone.

  4. MATE2 Mediates Vacuolar Sequestration of Flavonoid Glycosides and Glycoside Malonates in Medicago truncatula[C][W][OA

    Science.gov (United States)

    Zhao, Jian; Huhman, David; Shadle, Gail; He, Xian-Zhi; Sumner, Lloyd W.; Tang, Yuhong; Dixon, Richard A.

    2011-01-01

    The majority of flavonoids, such as anthocyanins, proanthocyanidins, and isoflavones, are stored in the central vacuole, but the molecular basis of flavonoid transport is still poorly understood. Here, we report the functional characterization of a multidrug and toxin extrusion transporter (MATE2), from Medicago truncatula. MATE 2 is expressed primarily in leaves and flowers. Despite its high similarity to the epicatechin 3′-O-glucoside transporter MATE1, MATE2 cannot efficiently transport proanthocyanidin precursors. In contrast, MATE2 shows higher transport capacity for anthocyanins and lower efficiency for other flavonoid glycosides. Three malonyltransferases that are coexpressed with MATE2 were identified. The malonylated flavonoid glucosides generated by these malonyltransferases are more efficiently taken up into MATE2-containing membrane vesicles than are the parent glycosides. Malonylation increases both the affinity and transport efficiency of flavonoid glucosides for uptake by MATE2. Genetic loss of MATE2 function leads to the disappearance of leaf anthocyanin pigmentation and pale flower color as a result of drastic decreases in the levels of various flavonoids. However, some flavonoid glycoside malonates accumulate to higher levels in MATE2 knockouts than in wild-type controls. Deletion of MATE2 increases seed proanthocyanidin biosynthesis, presumably via redirection of metabolic flux from anthocyanin storage. PMID:21467581

  5. Annotation and comparative analysis of the glycoside hydrolase genes in Brachypodium distachyon

    Energy Technology Data Exchange (ETDEWEB)

    Tyler, Ludmila [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany; Bragg, Jennifer [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany; Wu, Jiajie [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany; Yang, Xiaohan [ORNL; Tuskan, Gerald A [ORNL; Vogel, John [United States Department of Agriculture (USDA), Western Regional Research Center (WRRC), Albany

    2010-01-01

    Background Glycoside hydrolases cleave the bond between a carbohydrate and another carbohydrate, a protein, lipid or other moiety. Genes encoding glycoside hydrolases are found in a wide range of organisms, from archea to animals, and are relatively abundant in plant genomes. In plants, these enzymes are involved in diverse processes, including starch metabolism, defense, and cell-wall remodeling. Glycoside hydrolase genes have been previously cataloged for Oryza sativa (rice), the model dicotyledonous plant Arabidopsis thaliana, and the fast-growing tree Populus trichocarpa (poplar). To improve our understanding of glycoside hydrolases in plants generally and in grasses specifically, we annotated the glycoside hydrolase genes in the grasses Brachypodium distachyon (an emerging monocotyledonous model) and Sorghum bicolor (sorghum). We then compared the glycoside hydrolases across species, both at the whole-genome level and at the level of individual glycoside hydrolase families. Results We identified 356 glycoside hydrolase genes in Brachypodium and 404 in sorghum. The corresponding proteins fell into the same 34 families that are represented in rice, Arabidopsis, and poplar, helping to define a glycoside hydrolase family profile which may be common to flowering plants. Examination of individual glycoside hydrolase familes (GH5, GH13, GH18, GH19, GH28, and GH51) revealed both similarities and distinctions between monocots and dicots, as well as between species. Shared evolutionary histories appear to be modified by lineage-specific expansions or deletions. Within families, the Brachypodium and sorghum proteins generally cluster with those from other monocots. Conclusions This work provides the foundation for further comparative and functional analyses of plant glycoside hydrolases. Defining the Brachypodium glycoside hydrolases sets the stage for Brachypodium to be a monocot model for investigations of these enzymes and their diverse roles in planta. Insights

  6. Glycosides from Marine Sponges (Porifera, Demospongiae: Structures, Taxonomical Distribution, Biological Activities and Biological Roles

    Directory of Open Access Journals (Sweden)

    Valentin A. Stonik

    2012-08-01

    Full Text Available Literature data about glycosides from sponges (Porifera, Demospongiae are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed.

  7. Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles.

    Science.gov (United States)

    Kalinin, Vladimir I; Ivanchina, Natalia V; Krasokhin, Vladimir B; Makarieva, Tatyana N; Stonik, Valentin A

    2012-08-01

    Literature data about glycosides from sponges (Porifera, Demospongiae) are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed.

  8. Expression analysis and functional characterization of the monosaccharide transporters, OsTMTs, involving vacuolar sugar transport in rice (Oryza sativa).

    Science.gov (United States)

    Cho, Jung-Il; Burla, Bo; Lee, Dae-Woo; Ryoo, Nayeon; Hong, Soon-Kwan; Kim, Hyun-Bi; Eom, Joon-Seob; Choi, Sang-Bong; Cho, Man-Ho; Bhoo, Seong Hee; Hahn, Tae-Ryong; Neuhaus, H Ekkehard; Martinoia, Enrico; Jeon, Jong-Seong

    2010-05-01

    In Arabidopsis, the compartmentation of sugars into vacuoles is known to be facilitated by sugar transporters. However, vacuolar sugar transporters have not been studied in detail in other plant species. To characterize the rice (Oryza sativa) tonoplast monosaccharide transporters, OsTMT1 and OsTMT2, we analysed their subcellular localization using green fluorescent protein (GFP) and expression patterns using reverse-transcription polymerase chain reaction (RT-PCR), performed histochemical beta-glucuronidase (GUS) assay and in situ hybridization analysis, and assessed sugar transport ability using isolated vacuoles. Expression of OsTMT-GFP fusion protein in rice and Arabidopsis revealed that the OsTMTs localize at the tonoplast. Analyses of OsTMT promoter-GUS transgenic rice indicated that OsTMT1 and OsTMT2 are highly expressed in bundle sheath cells, and in vascular parenchyma and companion cells in leaves, respectively. Both genes were found to be preferentially expressed in the vascular tissues of roots, the palea/lemma of spikelets, and in the main vascular tissues and nucellar projections on the dorsal side of the seed coats. Glucose uptake studies using vacuoles isolated from transgenic mutant Arabidopsis (tmt1-2-3) expressing OsTMT1 demonstrated that OsTMTs are capable of transporting glucose into vacuoles. Based on expression analysis and functional characterization, our present findings suggest that the OsTMTs play a role in vacuolar glucose storage in rice.

  9. High throughput exopolysaccharide screening platform: from strain cultivation to monosaccharide composition and carbohydrate fingerprinting in one day.

    Science.gov (United States)

    Rühmann, Broder; Schmid, Jochen; Sieber, Volker

    2015-05-20

    Microbial exopolysaccharides (EPS) are multifunctional biogenic polymers, which exist in highly diverse chemical structures. To facilitate a fast determination of the carbohydrate composition of novel isolated strains or modified EPS variants a fast screening and analytical method is required. The platform as realized and described in this article is based on the fast carbohydrate analysis via liquid chromatography coupled with ultra violet and electrospray ionization ion trap detection in 96-well format to detect different sugars, sugar derivatives and substituents such as pyruvate. Monosaccharide analysis from hydrolyzed polysaccharides was validated successfully by 16 commercially available polymers with known structure. The method is sensitive enough to distinguish various types of sphingans which solely differ in small alterations in the monomer composition. Even a quantitative detection of single monomers as present in complex plant polysaccharides like karaya gum, with the lowest recovery, was in accordance with literature. Furthermore, 94 bacterial strains for the validation of the screening platform were completely analyzed and 41 EPS producing strains were efficiently identified. Using the method a carbohydrate-fingerprint of the strains was obtained even allowing a very fast differentiation between strains belonging to the same species. This method can become a valuable tool not only in the fast analysis of strain isolates but also in the targeted screening for polysaccharides containing special rare sugars as well in the screening of strain libraries from genetic engineering for altered structures. Copyright © 2015 The Authors. Published by Elsevier Ltd.. All rights reserved.

  10. Ehealth monitoring in irritable bowel syndrome patients treated with low fermentable oligo-, di-, mono-saccharides and polyols diet

    Science.gov (United States)

    Pedersen, Natalia; Vegh, Zsuzsanna; Burisch, Johan; Jensen, Lisbeth; Ankersen, Dorit Vedel; Felding, Maria; Andersen, Nynne Nyboe; Munkholm, Pia

    2014-01-01

    In the present study we report on changes in irritable bowel syndrome-severity scoring system (IBS-SSS) and irritable bowel syndrome-quality of life (IBS-QoL) in 19 IBS patients, aged 18 to 74 years (F/M: 14/5), during 12 wk registering their symptoms on the web-application (www.ibs.constant-care.dk). During a control period of the first 6-wk patients were asked to register their IBS-SSS and IBS-QoL on the web-application weekly without receiving any intervention. Thereafter, low fermentable oligo-, di-, mono-saccharides and polyols (FODMAP) diet (LFD) was introduced for the next 6 wk while continuing the registration. Though a small sample size a significant improvement in disease activity (IBS-SSS) was observed during both the control period, median: 278 (range: 122-377), P = 0.02, and subsequently during the LFD period, median: 151 (range: 29-334), P < 0.01. The IBS-QoL solely changed significantly during the LFD period, median: 67 (37-120), P < 0.01. The significant reduction in disease activity during the control period shows a positive effect of the web-application on IBS symptoms when presented as a “traffic light”. However adding the diet reduced IBS-SSS to < 150, inactive to mild symptoms. In the future results from larger scale trials are awaited. PMID:24914395

  11. Using monosaccharide anhydrides to estimate the impact of wood combustion on fine particles in the Helsinki Metropolitan Area

    Energy Technology Data Exchange (ETDEWEB)

    Saarnio, K.; Saarikoski, S. [Finnish Meteorological Institute, Helsinki (Finland); Niemi, J.V. [HSY Helsinki Region Environmental Services Authority, Helsinki (Finland)

    2012-11-01

    The spatiotemporal variation of ambient particles under the influence of biomass burning emissions was studied in the Helsinki Metropolitan Area (HMA) in selected periods during 2005-2009. Monosaccharide anhydrides (MAs; levoglucosan, mannosan and galactosan), commonly known biomass burning tracers, were used to estimate the wood combustion contribution to local particulate matter (PM) concentration levels at three urban background sites close to the city centre, and at three suburban sites influenced by local small-scale wood combustion. In the cold season (October-March), the mean MAs concentrations were 115-225 ng m{sup -3} and 83-98 ng m{sup -} {sup 3}at the suburban and urban sites, respectively. In the warm season, the mean MAs concentrations were low (19-78 ng m{sup -3}), excluding open land fire smoke episodes (222-378 ng m{sup -}3{sup )}. Regionally distributed wood combustion particles raised the levels over the whole HMA while particles from local wood combustion sources raised the level at suburban sites only. The estimated average contribution of wood combustion to fine particles (PM{sub 2.5}) ranged from 18% to 29% at the urban sites and from 31% to 66% at the suburban sites in the cold season. The PM measurements from ambient air and combustion experiments showed that the proportions of the three MAs can be utilised to separate the wildfire particles from residential wood combustion particles. (orig.)

  12. Steroidal glycosides from the rhizomes of Ruscus hypophyllum.

    Science.gov (United States)

    Mimaki, Yoshihiro; Aoki, Tsukasa; Jitsuno, Maki; Kiliç, Ceyda Sibel; Coşkun, Maksut

    2008-02-01

    Seven steroidal glycosides, along with one known glycoside, were isolated from the rhizomes of Ruscus hypophyllum (Liliaceae). Comprehensive spectroscopic analysis, including 2D NMR spectroscopy, and the results of acid hydrolysis allowed the chemical structures of the compounds to be assigned as (23S,25R)-23-hydroxyspirost-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (1), 1beta-hydroxyspirosta-5,25(27)-dien-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (2), (22S)-16beta,22-dihydroxycholest-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (3), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (4), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3beta-yl beta-d-glucopyranoside (5), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-3beta,22-dihydroxycholest-5-en-1beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl-beta-d-xylopyranoside) (6), and (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-3beta,22-dihydroxycholest-5-en-1beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-O-[beta-d-xylopyranosyl-(1-->3)]-beta-d-xylopyranoside (7), respectively. This is the first isolation of a series of cholestane glycosides from a Ruscus species.

  13. O-Fucose Monosaccharide of Drosophila Notch Has a Temperature-sensitive Function and Cooperates with O-Glucose Glycan in Notch Transport and Notch Signaling Activation*

    Science.gov (United States)

    Ishio, Akira; Sasamura, Takeshi; Ayukawa, Tomonori; Kuroda, Junpei; Ishikawa, Hiroyuki O.; Aoyama, Naoki; Matsumoto, Kenjiroo; Gushiken, Takuma; Okajima, Tetsuya; Yamakawa, Tomoko; Matsuno, Kenji

    2015-01-01

    Notch (N) is a transmembrane receptor that mediates the cell-cell interactions necessary for many cell fate decisions. N has many epidermal growth factor-like repeats that are O-fucosylated by the protein O-fucosyltransferase 1 (O-Fut1), and the O-fut1 gene is essential for N signaling. However, the role of the monosaccharide O-fucose on N is unclear, because O-Fut1 also appears to have O-fucosyltransferase activity-independent functions, including as an N-specific chaperon. Such an enzymatic activity-independent function could account for the essential role of O-fut1 in N signaling. To evaluate the role of the monosaccharide O-fucose modification in N signaling, here we generated a knock-in mutant of O-fut1 (O-fut1R245A knock-in), which expresses a mutant protein that lacks O-fucosyltransferase activity but maintains the N-specific chaperon activity. Using O-fut1R245A knock-in and other gene mutations that abolish the O-fucosylation of N, we found that the monosaccharide O-fucose modification of N has a temperature-sensitive function that is essential for N signaling. The O-fucose monosaccharide and O-glucose glycan modification, catalyzed by Rumi, function redundantly in the activation of N signaling. We also showed that the redundant function of these two modifications is responsible for the presence of N at the cell surface. Our findings elucidate how different forms of glycosylation on a protein can influence the protein's functions. PMID:25378397

  14. O-fucose monosaccharide of Drosophila Notch has a temperature-sensitive function and cooperates with O-glucose glycan in Notch transport and Notch signaling activation.

    Science.gov (United States)

    Ishio, Akira; Sasamura, Takeshi; Ayukawa, Tomonori; Kuroda, Junpei; Ishikawa, Hiroyuki O; Aoyama, Naoki; Matsumoto, Kenjiroo; Gushiken, Takuma; Okajima, Tetsuya; Yamakawa, Tomoko; Matsuno, Kenji

    2015-01-02

    Notch (N) is a transmembrane receptor that mediates the cell-cell interactions necessary for many cell fate decisions. N has many epidermal growth factor-like repeats that are O-fucosylated by the protein O-fucosyltransferase 1 (O-Fut1), and the O-fut1 gene is essential for N signaling. However, the role of the monosaccharide O-fucose on N is unclear, because O-Fut1 also appears to have O-fucosyltransferase activity-independent functions, including as an N-specific chaperon. Such an enzymatic activity-independent function could account for the essential role of O-fut1 in N signaling. To evaluate the role of the monosaccharide O-fucose modification in N signaling, here we generated a knock-in mutant of O-fut1 (O-fut1(R245A knock-in)), which expresses a mutant protein that lacks O-fucosyltransferase activity but maintains the N-specific chaperon activity. Using O-fut1(R245A knock-in) and other gene mutations that abolish the O-fucosylation of N, we found that the monosaccharide O-fucose modification of N has a temperature-sensitive function that is essential for N signaling. The O-fucose monosaccharide and O-glucose glycan modification, catalyzed by Rumi, function redundantly in the activation of N signaling. We also showed that the redundant function of these two modifications is responsible for the presence of N at the cell surface. Our findings elucidate how different forms of glycosylation on a protein can influence the protein's functions. © 2015 by The American Society for Biochemistry and Molecular Biology, Inc.

  15. Two New Glycosides from the Fruits of Morinda citrifolia L.

    Directory of Open Access Journals (Sweden)

    Yu Wang

    2012-10-01

    Full Text Available To study the chemical constituents of the fruits of noni (Morinda citrifolia L., and find novel compounds, an n-butanol extract of the ethanol soluble fraction was subjected to repeated silica gel and ODS column chromatography and HPLC. Two new glycosides were isolated and their structures elucidated by NMR and HRFAB-MS spectrometry as (2E,4E,7Z-deca-2,4,7-trienoate-2-O-β-D-glucopyranosyl-β-D-glucopyra-noside (1 and amyl-1-O-β-D-apio-furanosyl-1,6-O-β-D-glucopyranoside (2, respectively.

  16. Two new glycosides from the fruits of Morinda citrifolia L.

    Science.gov (United States)

    Hu, Ming-Xu; Zhang, Hong-Cai; Wang, Yu; Liu, Shu-Min; Liu, Li

    2012-10-26

    To study the chemical constituents of the fruits of noni (Morinda citrifolia L.), and find novel compounds, an n-butanol extract of the ethanol soluble fraction was subjected to repeated silica gel and ODS column chromatography and HPLC. Two new glycosides were isolated and their structures elucidated by NMR and HRFAB-MS spectrometry as (2E,4E,7Z)-deca-2,4,7-trienoate-2-O-β-D-glucopyranosyl-β-D-glucopyranoside and amyl-1-O-β-D-apio-furanosyl-1,6-O-β-D-glucopyranoside, respectively.

  17. New cyclopeptide alkaloid and lignan glycoside from Justicia procumbens.

    Science.gov (United States)

    Jin, Hong; Chen, Li; Tian, Ying; Li, Bin; Dong, Jun-Xing

    2015-01-01

    This study reported a new cyclopeptide alkaloid, justicianene A (1), and a new lignan glycoside, procumbenoside H (2), isolated from Justicia procumbens. The structures of the new compounds were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies and mass spectrometry. Cyclopeptide alkaloids were first observed from the genus Justicia. Compound 2 was cytotoxic against human LoVo colon carcinoma cells with an IC50 value of 17.908 ± 1.949 μM.

  18. Pharmacological activities and mechanisms of natural phenylpropanoid glycosides.

    Science.gov (United States)

    Pan, Jing; Yuan, Chengshan; Lin, Changjun; Jia, Zhongjian; Zheng, Rongliang

    2003-11-01

    The pharmacological activities and mechanisms of action of natural phenylpropanoid glycosides extracted from a variety of plants are summarized in this review, such as antitumor, antivirus, anti-inflammation, antibacteria, antiartherosclerosis, anti-platelet-aggregation, antihypertension, antifatigue, analgesia, hepatoprotection, immunosuppression, protection of sex and learning behavior, protection of neurodegeneration, reverse transformation of tumor cells, inhibition of telomerase and shortening telomere length in tumor cells, effects on enzymes and cytokines, antioxidation, free radical scavenging and fast repair of oxidative damaged DNA. Molecular modeling is discussed as well as structure-activity relationships.

  19. A new phenolic glycoside from Spiraea prunifolia var. simpliciflora twigs.

    Science.gov (United States)

    Jang, Sung Wan; Suh, Won Se; Kim, Chung Sub; Kim, Ki Hyun; Lee, Kang Ro

    2015-11-01

    The phytochemical investigation of the methanol extract from the twigs of Spiraea prunifolia var. simpliciflora (Rosaceae) using column chromatography led to the isolation of a new phenol glycoside, 1-O-(E)-caffeoyl-2-O-p-(E)-coumaroyl-β-D-glucopyranose (1), together with 16 known phenolic compounds (2-17). The structure of this new compound was elucidated by analysis of spectroscopic data including 1D, 2D nuclear magnetic resonance and HR-FAB-MS data. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using the sulforhodamine B bioassay.

  20. Two New Flavone Glycosides from Chenopodiumambrosioides Growing Wildly in Egypt

    Directory of Open Access Journals (Sweden)

    Hala M. Hammoda

    2015-06-01

    Full Text Available Chenopodiumambrosioides (Chenopodiaceae growing wildly in Egypt was subjected to antioxidant –guided phytochemical investigation and the EtOAc fraction afforded the two new flavone glycosides; scutellarein-7-O-α-rhamnopyranosyl-(1→2-α-rhamnopyranosyl-(1→2-α-rhamnopyranoside (1 and scutella-rein-7-O-α-rhamnopyranosyl-(1→2-α-rhamnopyranoside (2. In addition, the invitro antioxidant activities of the plant alcohol extract, CHCl 3 fraction, EtOAc fraction and isolates were studied.

  1. Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides

    DEFF Research Database (Denmark)

    Rønsted, N.; Göbel, E.; Franzyk, Henrik

    2000-01-01

    Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (=Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and man...... in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis, could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera. (C) 2000 Elsevier Science Ltd. All rights reserved....

  2. [HPLC fingerprinting of total glycosides of Swertia franchetiana].

    Science.gov (United States)

    Tian, Wei; Chen, Zhao-hui; Zhai, Jing; Chen, Li-ren; Li, Yong-min

    2005-05-01

    To establish a sensitive and specific HPLC method for controlling the quality of total glycosides from Swertia franchetiana H. Smith. HPLC method was applied for quality and quantitative assessment of the pharmaceutical extracts from Swertia franchetiana H. Smith. The preparation of sample, the HPLC column, mobile phase, elution mode (isocratic or gradient) and gradient program were optimized in order to obtain HPLC profile. The HPLC system consisted of a SPD-1OAvp pump, SPD-M1OAVP photodiode-array detector (PAD), SIL-10ADVP auto injector. Data were acquired and processed with the CLASS-VP6.1 workstation. HPLC analysis was performed on a Kromasil C18 column (250 mm x 4. 6 mm ID, 5 microm) with methanol and water as mobile phase. The column temperature was set up at 40 degrees C and the flow-rate was 1 mL x min(-1). The reference solution of chemical standards and sample were injected into HPLC system, separately. The HPLC chromatographic fingerprinting of the total glycosides, showing 16 characteristic peaks which were partitioned into three parts: one peak in 0-10 min of retention time, nine peaks containing main 1-7 peaks in 10-15 min of retention time, 6 peaks in 15-30 min of retention time, was established from 10 lots of their products. By comparison of the retention time and the on-line UV spectra and their molecule weights of chemical standards, peak 1-7 were identified as swertiamarin (1), gentiopicroside (2), sweroside (3), isoorientin (4), swertisin (5), isoswertisin (6) and swetianolin (7), respectively. The ratios of peak area between 1-16 were in their extent. Moreover, comparison of the HPLC profiles of the total glycosides, the extracts prepared using another process and the plant indicated that they were closely related to each other. The HPLC profiles and quantitative assessment of the total glycosides from Swertia franchetiana H. Smith with high specificity can be used to control their quality and assure lot to lot consistency.

  3. Additional New Minor Cucurbitane Glycosides from Siraitia grosvenorii

    Directory of Open Access Journals (Sweden)

    Indra Prakash

    2014-03-01

    Full Text Available Continuous phytochemical studies of the crude extract of Luo Han Guo (Siraitia grosvenorii furnished three additional new cucurbitane triterpene glycosides, namely 11-deoxymogroside V, 11-deoxyisomogroside V, and 11-deoxymogroside VI. The structures of all the isolated compounds were characterized on the basis of extensive NMR and mass spectral data as well as hydrolysis studies. The complete 1H- and 13C-NMR spectral assignments of the three unknown compounds are reported for the first time based on COSY, TOCSY, HSQC, and HMBC spectroscopic data.

  4. Calysolins I-IV, resin glycosides from Calystegia soldanella.

    Science.gov (United States)

    Takigawa, Ayako; Muto, Haruka; Kabata, Kiyotaka; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro; Ono, Masateru

    2011-11-28

    Four new resin glycosides having intramolecular cyclic ester structures (jalapins), named calysolins I-IV (1-4), were isolated from the methanol extract of leaves, stems, and roots of Calystegia soldanella , along with one known jalapin (5) derivative. The structures of 1-4 were determined on the basis of spectroscopic data and chemical evidence. They fall into two types, one having a 22-membered ring (1 and 4) and the other with a 27-membered ring (2 and 3). The sugar moieties of 1-4 were partially acylated by some organic acids. Compound 4 is the first example of a hexaglycoside of jalapin.

  5. Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus

    Directory of Open Access Journals (Sweden)

    Jun-Xia Kang

    2016-10-01

    Full Text Available Three new polyhydroxysteroidal glycosides, hesperuside A (1, B (2, and C (3, as well as a known novaeguinoside A (4, were isolated from the ethanol extract of starfish Craspidaster hesperus collected from the South China Sea. Their structures were elucidated by extensive spectroscopic methods and chemical evidence. The compounds 1–3 present unprecedented carbohydrate chain 3-O-methyl-β-d-galactopyranose, which differ from each other in the side chains. These compounds exhibited cytotoxicity against human tumor cells BEL-7402, MOLT-4, and A-549 in vitro.

  6. Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus.

    Science.gov (United States)

    Kang, Jun-Xia; Kang, Yong-Feng; Han, Hua

    2016-10-19

    Three new polyhydroxysteroidal glycosides, hesperuside A (1), B (2), and C (3), as well as a known novaeguinoside A (4), were isolated from the ethanol extract of starfish Craspidaster hesperus collected from the South China Sea. Their structures were elucidated by extensive spectroscopic methods and chemical evidence. The compounds 1-3 present unprecedented carbohydrate chain 3-O-methyl-β-d-galactopyranose, which differ from each other in the side chains. These compounds exhibited cytotoxicity against human tumor cells BEL-7402, MOLT-4, and A-549 in vitro.

  7. A New Flavonoid Glycoside from Salix denticulata Aerial Parts

    Directory of Open Access Journals (Sweden)

    Amita Bamola

    2009-09-01

    Full Text Available Abstract: A new flavonoid glycoside (1 has been isolated from the aerial parts of Salix denticulata (Salicaceae together with five known compounds, β-sitosterol, 2,6-dihydroxy- 4-methoxy acetophenone, eugenol-1-O-β-D-glucopyranoside, 1-O-β-D-(3’-benzoyl salicyl alcohol and luteolin-7-O-β-D-glucopyranosyl-(1-6-glucopyranoside. The structure of 1 was elucidated as 2’,5-dihydroxy-3’-methoxyflavone-7-O-β-D-glucopyranoside by means of chemical and spectral data including 2D NMR studies.

  8. Investigations of Reactive Carbohydrates in Glycosidic Bond Formation and Degradation

    DEFF Research Database (Denmark)

    Heuckendorff, Mads

    was to develop new synthetic methods to evolve the field of synthetic carbohydrate chemistry. In addition, easy methods for obtaining complex oligosaccharides are needed to accommodate biochemical research and drug development. Furthermore, the aim was to shed light on the complex mechanisms of glycosylation...... and hy rolysis of glycosides. This mechanistic insight can then be used to develop new synthetic methods and obtain a better understanding of already existing methods. In Chapter 1 general aspects of synthetic carbohydrate chemistry is described with an emphasis on elements that affects reactivity...

  9. Acylated flavonol glycosides from the flower of Inula britannica.

    Science.gov (United States)

    Park, E J; Kim, Y; Kim, J

    2000-01-01

    Three new acylated flavonol glycosides, patuletin 7-O-(6' '-isobutyryl)glucoside (1), patuletin 7-O-[6' '-(2-methylbutyryl)]glucoside (2), and patuletin 7-O-(6' '-isovaleryl)glucoside (3), were isolated from the n-BuOH extract of Inula britannica flowers by bioassay-guided fractionation, together with other known flavonoids. The structures were elucidated by 1D and 2D NMR, FABMS, and other spectral analyses. The eight flavonoids, including new compounds (1-3), patulitrin (7), nepitrin (8), axillarin (10), patuletin (11), and luteolin (12), showed profound antioxidant activity in DPPH assay and cytochrome-c reduction assay using HL-60 cell culture system.

  10. Changes in monosaccharides, organic acids and amino acids during Cabernet Sauvignon wine ageing based on a simultaneous analysis using gas chromatography-mass spectrometry.

    Science.gov (United States)

    Zhang, Xin-Ke; Lan, Yi-Bin; Zhu, Bao-Qing; Xiang, Xiao-Feng; Duan, Chang-Qing; Shi, Ying

    2018-01-01

    Monosaccharides, organic acids and amino acids are the important flavour-related components in wines. The aim of this article is to develop and validate a method that could simultaneously analyse these compounds in wine based on silylation derivatisation and gas chromatography-mass spectrometry (GC-MS), and apply this method to the investigation of the changes of these compounds and speculate upon their related influences on Cabernet Sauvignon wine flavour during wine ageing. This work presented a new approach for wine analysis and provided more information concerning red wine ageing. This method could simultaneously quantitatively analyse 2 monosaccharides, 8 organic acids and 13 amino acids in wine. A validation experiment showed good linearity, sensitivity, reproducibility and recovery. Multiple derivatives of five amino acids have been found but their effects on quantitative analysis were negligible, except for methionine. The evolution pattern of each category was different, and we speculated that the corresponding mechanisms involving microorganism activities, physical interactions and chemical reactions had a great correlation with red wine flavours during ageing. Simultaneously quantitative analysis of monosaccharides, organic acids and amino acids in wine was feasible and reliable and this method has extensive application prospects. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

  11. Two new nor-triterpene glycosides from peruvian "Uña de Gato" (Uncaria tomentosa).

    Science.gov (United States)

    Kitajima, Mariko; Hashimoto, Ken-Ichiro; Yokoya, Masashi; Takayama, Hiromitsu; Sandoval, Manuel; Aimi, Norio

    2003-02-01

    Two new 27-nor-triterpene glycosides, tomentosides A (1) and B (2), were isolated from Peruvian "Uña de Gato" (cat's claw, plant of origin: Uncaria tomentosa), a traditional herbal medicine in Peru. Their structures were determined by spectroscopic analysis and chemical interconversions. This is the first report of naturally occurring pyroquinovic acid glycosides.

  12. New cardenolide and acylated lignan glycosides from the aerial parts of Asclepias curassavica.

    Science.gov (United States)

    Warashina, Tsutomu; Shikata, Kimiko; Miyase, Toshio; Fujii, Satoshi; Noro, Tadataka

    2008-08-01

    Three new cardenolide glycosides and six new acylated lignan glycosides were obtained along with nineteen known compounds from the aerial parts of Asclepias curassavica L. (Asclepiadaceae). The structure of each compound was determined based on interpretations of NMR and MS measurements and chemical evidence.

  13. A New Resin Glycoside, Muricatin IX, from the Seeds of Ipomoea muricata.

    Science.gov (United States)

    Ono, Masateru; Taketomi, Saki; Kakiki, Yuichi; Yasuda, Shin; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

    2016-01-01

    A new resin glycoside, named muricatin IX (1), was isolated from the seeds of Ipomoea muricata (L.) JACQ. (Convolvulaceae). The structure of 1 was determined on the basis of spectroscopic data as well as chemical evidence. Compound 1 is the first representative of resin glycosides in which an organic acid connects the sugar moiety and the aglycone moiety to form macrocyclic ester ring.

  14. Bioaccessibility, Intestinal Permeability and Plasma Stability of Isorhamnetin Glycosides from Opuntia ficus-indica (L.).

    Science.gov (United States)

    Antunes-Ricardo, Marilena; Rodríguez-Rodríguez, César; Gutiérrez-Uribe, Janet A; Cepeda-Cañedo, Eduardo; Serna-Saldívar, Sergio O

    2017-08-22

    Isorhamnetin glycosides are representative compounds of Opuntia ficus-indica that possess different biological activities. There is slight information about the changes in bioaccessibility induced by the glycosylation pattern of flavonoids, particularly for isorhamnetin. In this study, the bioaccessibility and permeability of isorhamnetin glycosides extracted from O. ficus-indica were contrasted with an isorhamnetin standard. Also, the plasma stability of these isorhamnetin glycosides after intravenous administration in rats was evaluated. Recoveries of isorhamnetin after oral and gastric digestion were lower than that observed for its glycosides. After intestinal digestion, isorhamnetin glycosides recoveries were reduced to less than 81.0%. The apparent permeability coefficient from apical (AP) to basolateral (BL) direction (Papp(AP-BL)) of isorhamnetin was 2.6 to 4.6-fold higher than those obtained for its glycosides. Isorhamnetin diglycosides showed higher Papp(AP-BL) values than triglycosides. Sugar substituents affected the Papp(AP-BL) of the triglycosides. Isorhamnetin glycosides were better retained in the circulatory system than the aglycone. After intravenous dose of the isorhamnetin standard, the elimination half-life was 0.64 h but increased to 1.08 h when the O. ficus-indica extract was administered. These results suggest that isorhamnetin glycosides naturally found in O. ficus-indica could be a controlled delivery system to maintain a constant plasmatic concentration of this important flavonoid to exert its biological effects in vivo.

  15. Anti-HIV diphyllin glycosides from Justicia gendarussa.

    Science.gov (United States)

    Zhang, Hong-Jie; Rumschlag-Booms, Emily; Guan, Yi-Fu; Liu, Kang-Lun; Wang, Dong-Ying; Li, Wan-Fei; Nguyen, Van Hung; Cuong, Nguyen Manh; Soejarto, Djaja Doel; Fong, Harry H S; Rong, Lijun

    2017-04-01

    In a search for new anti-HIV active leads from over several thousands of plant extracts, we have identified a potent plant lead. The active plant is determined as Justicia gendarussa (Acanthaceae), a medicinal plant that has been used for the treatment of injury, arthritis and rheumatism in Asia including China. Our bioassay-guided fractionation of the methanol extract of the stems and barks of the plant led to the isolation of two anti-HIV compounds, justiprocumins A and B. The compounds are identified as new arylnaphthalide lignans (ANL) glycosides. We further determined that the ANL glycosides are the chemical constituents that contribute to the anti-HIV activity of this plant. Justiprocumin B displayed potent activity against a broad spectrum of HIV strains with IC 50 values in the range of 15-21 nM (AZT, IC 50 77-95 nM). The compound also displayed potent inhibitory activity against the NRTI (nucleoside reverse transcriptase inhibitor)-resistant isolate (HIV-1 1617-1 ) of the analogue (AZT) as well as the NNRTI (non-nucleoside reverse transcriptase inhibitor)-resistant isolate (HIV-1 N119 ) of the analogue (nevaripine). Copyright © 2017 Elsevier Ltd. All rights reserved.

  16. Potent antiviral flavone glycosides from Ficus benjamina leaves.

    Science.gov (United States)

    Yarmolinsky, Ludmila; Huleihel, Mahmoud; Zaccai, Michele; Ben-Shabat, Shimon

    2012-03-01

    Crude ethanol extracts from Ficus benjamina leaves strongly inhibit Herpes Simplex Virus 1 and 2 (HSV-1/2) as well as Varicella Zoster Virus (VZV) cell infection in vitro. Bioassay-guided fractionation of the crude extract demonstrated that the most efficient inhibition of HSV-1 and HSV-2 was obtained with the flavonoid fraction. The present study was aimed to further isolate, purify and identify substances with potent antiviral activity from the flavonoid fraction of F. benjamina extracts. Flavonoids were collected from the leaf ethanol extracts through repeated purification procedure and HPLC analysis. The antiviral activity of each substance was then evaluated in cell culture. Three known flavone glycosides, (1) quercetin 3-O-rutinoside, (2) kaempferol 3-O-rutinoside and (3) kaempferol 3-O-robinobioside, showing highest antiviral efficiency were selected and their structure was determined by spectroscopic analyses including NMR and mass spectrometry (MS). These three flavones were highly effective against HSV-1 reaching a selectivity index (SI) of 266, 100 and 666 for compound 1, 2 and 3, respectively, while the SI of their aglycons, quercetin and kaempferol amounted only in 7.1 and 3.2, respectively. Kaempferol 3-O-robinobioside showed similar SI to that of acyclovir (ACV), the standard anti-HSV drug. Although highly effective against HSV-1 and HSV-2, these flavone glycosides did not show any significant activity against VZV. Copyright © 2011 Elsevier B.V. All rights reserved.

  17. Flavonoid Glycosides from Siparuna gigantotepala Leaves and Their Antioxidant Activity.

    Science.gov (United States)

    Torres Castañeda, Harlen Gerardo; Colmenares Dulcey, Ana Julia; Isaza Martínez, José Hipólito

    2016-01-01

    Two new flavonol glycosides were isolated from the leaves of Siparuna gigantotepala. Their structures were determined to be kaempferol 3-O-β-xylopyranosyl-(1→2)-α-arabinofuranoside (1) and kaempferol 3,7-di-O-methyl-4'-O-α-rhamnopyranosyl-(1→2)-β-glucopyranoside (2). In addition, three known flavonol glycosides, rutin (3), kaempferol 3-O-rutinoside (4), and kaempferol 3,7-di-O-methyl-4'-O-rutinoside (5), and three flavonol aglycones, quercetin (6), kaempferol 3,7-dimethyl ether (7), and kaempferol 3,7,4'-trimethyl ether (8), were also isolated and are reported here for the first time in this species. The structures of compounds 1 and 2 were established on the basis of their LC-MS and one- and two-dimensional (1D)- and (2D)-NMR spectroscopic analyses, combined with acid methanolysis and silylation of sugar moieties for GC-MS. Evaluation of the antioxidant activity, conducted in the 96-well plate format, showed that the flavonoids isolated possess strong 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity and moderate oxygen radical absorption capacity.

  18. Iridoid glycosides from the root of Acanthus sennii

    Directory of Open Access Journals (Sweden)

    Etagegnehu Assefa

    2016-12-01

    Full Text Available Context: Acanthus sennii is a plant traditionally used for the treatment of antifungal, cytotoxic, anti-inflammatory, antipyretic, antioxidant, insecticidal, hepatoprotective, immunomodulatory, anti-platelet aggregation and anti-viral potential. Aims: To investigate the phytochemical constituents of roots of Acanthus sennii. Methods: Phytochemical screening tests were conducted to identify the class of compounds present in the root extract. Silica gel column chromatographic technique was applied to separate the constituents of the extracts. Various spectroscopic techniques (IR, 1H NMR, 13C NMR, DEPT-135, COSY, gHSQC, and gHMBC were applied to determine the structures of isolated compounds. Results: Phytochemical screening of the dichloromethane/methanol (1:1 and methanol (100% root extract of the plant revealed the presence of phenolic compounds, steroids, flavonoids, and terpenes. Chromatographic separation of dichloromethane/methanol (1:1 root extract of Acanthus sennii yielded two iridoid glycosides (1, 2. Conclusions: The roots of Acanthus senni contain various class of constituents such as flavonoids, phenols, terpenoids, tannins, and iridoid glycosides identified through phytochemical screening test and purification process, which might be responsible for the traditional use of the plant. To the best of our knowledge, these compounds are isolated for the first time from this genus.

  19. Recovering glycoside hydrolase genes from active tundra cellulolytic bacteria.

    Science.gov (United States)

    Pinnell, Lee J; Dunford, Eric; Ronan, Patrick; Hausner, Martina; Neufeld, Josh D

    2014-07-01

    Bacteria responsible for cellulose hydrolysis in situ are poorly understood, largely because of the relatively recent development of cultivation-independent methods for their detection and characterization. This study combined DNA stable-isotope probing (DNA-SIP) and metagenomics for identifying active bacterial communities that assimilated carbon from glucose and cellulose in Arctic tundra microcosms. Following DNA-SIP, bacterial fingerprint analysis of gradient fractions confirmed isotopic enrichment. Sequenced fingerprint bands and clone library analysis of 16S rRNA genes identified active bacterial taxa associated with cellulose-associated labelled DNA, including Bacteroidetes (Sphingobacteriales), Betaproteobacteria (Burkholderiales), Alphaproteobacteria (Caulobacteraceae), and Chloroflexi (Anaerolineaceae). We also compared glycoside hydrolase metagenomic profiles from bulk soil and heavy DNA recovered from DNA-SIP incubations. Active populations consuming [(13)C]glucose and [(13)C]cellulose were distinct, based on ordinations of light and heavy DNA. Metagenomic analysis demonstrated a ∼3-fold increase in the relative abundance of glycoside hydrolases in DNA-SIP libraries over bulk-soil libraries. The data also indicate that multiple displacement amplification introduced bias into the resulting metagenomic analysis. This research identified DNA-SIP incubation conditions for glucose and cellulose that were suitable for Arctic tundra soil and confirmed that DNA-SIP enrichment can increase target gene frequencies in metagenomic libraries.

  20. Steviol glycosides modulate glucose transport in different cell types.

    Science.gov (United States)

    Rizzo, Benedetta; Zambonin, Laura; Angeloni, Cristina; Leoncini, Emanuela; Dalla Sega, Francesco Vieceli; Prata, Cecilia; Fiorentini, Diana; Hrelia, Silvana

    2013-01-01

    Extracts from Stevia rebaudiana Bertoni, a plant native to Central and South America, have been used as a sweetener since ancient times. Currently, Stevia extracts are largely used as a noncaloric high-potency biosweetener alternative to sugar, due to the growing incidence of type 2 diabetes mellitus, obesity, and metabolic disorders worldwide. Despite the large number of studies on Stevia and steviol glycosides in vivo, little is reported concerning the cellular and molecular mechanisms underpinning the beneficial effects on human health. The effect of four commercial Stevia extracts on glucose transport activity was evaluated in HL-60 human leukaemia and in SH-SY5Y human neuroblastoma cells. The extracts were able to enhance glucose uptake in both cellular lines, as efficiently as insulin. Our data suggest that steviol glycosides could act by modulating GLUT translocation through the PI3K/Akt pathway since treatments with both insulin and Stevia extracts increased the phosphorylation of PI3K and Akt. Furthermore, Stevia extracts were able to revert the effect of the reduction of glucose uptake caused by methylglyoxal, an inhibitor of the insulin receptor/PI3K/Akt pathway. These results corroborate the hypothesis that Stevia extracts could mimic insulin effects modulating PI3K/Akt pathway.

  1. Steviol Glycosides Modulate Glucose Transport in Different Cell Types

    Directory of Open Access Journals (Sweden)

    Benedetta Rizzo

    2013-01-01

    Full Text Available Extracts from Stevia rebaudiana Bertoni, a plant native to Central and South America, have been used as a sweetener since ancient times. Currently, Stevia extracts are largely used as a noncaloric high-potency biosweetener alternative to sugar, due to the growing incidence of type 2 diabetes mellitus, obesity, and metabolic disorders worldwide. Despite the large number of studies on Stevia and steviol glycosides in vivo, little is reported concerning the cellular and molecular mechanisms underpinning the beneficial effects on human health. The effect of four commercial Stevia extracts on glucose transport activity was evaluated in HL-60 human leukaemia and in SH-SY5Y human neuroblastoma cells. The extracts were able to enhance glucose uptake in both cellular lines, as efficiently as insulin. Our data suggest that steviol glycosides could act by modulating GLUT translocation through the PI3K/Akt pathway since treatments with both insulin and Stevia extracts increased the phosphorylation of PI3K and Akt. Furthermore, Stevia extracts were able to revert the effect of the reduction of glucose uptake caused by methylglyoxal, an inhibitor of the insulin receptor/PI3K/Akt pathway. These results corroborate the hypothesis that Stevia extracts could mimic insulin effects modulating PI3K/Akt pathway.

  2. Steviol Glycosides Modulate Glucose Transport in Different Cell Types

    Science.gov (United States)

    Rizzo, Benedetta; Zambonin, Laura; Leoncini, Emanuela; Vieceli Dalla Sega, Francesco; Prata, Cecilia; Fiorentini, Diana; Hrelia, Silvana

    2013-01-01

    Extracts from Stevia rebaudiana Bertoni, a plant native to Central and South America, have been used as a sweetener since ancient times. Currently, Stevia extracts are largely used as a noncaloric high-potency biosweetener alternative to sugar, due to the growing incidence of type 2 diabetes mellitus, obesity, and metabolic disorders worldwide. Despite the large number of studies on Stevia and steviol glycosides in vivo, little is reported concerning the cellular and molecular mechanisms underpinning the beneficial effects on human health. The effect of four commercial Stevia extracts on glucose transport activity was evaluated in HL-60 human leukaemia and in SH-SY5Y human neuroblastoma cells. The extracts were able to enhance glucose uptake in both cellular lines, as efficiently as insulin. Our data suggest that steviol glycosides could act by modulating GLUT translocation through the PI3K/Akt pathway since treatments with both insulin and Stevia extracts increased the phosphorylation of PI3K and Akt. Furthermore, Stevia extracts were able to revert the effect of the reduction of glucose uptake caused by methylglyoxal, an inhibitor of the insulin receptor/PI3K/Akt pathway. These results corroborate the hypothesis that Stevia extracts could mimic insulin effects modulating PI3K/Akt pathway. PMID:24327825

  3. Allosteric indicator displacement enzyme assay for a cyanogenic glycoside.

    Science.gov (United States)

    Jose, D Amilan; Elstner, Martin; Schiller, Alexander

    2013-10-18

    Indicator displacement assays (IDAs) represent an elegant approach in supramolecular analytical chemistry. Herein, we report a chemical biosensor for the selective detection of the cyanogenic glycoside amygdalin in aqueous solution. The hybrid sensor consists of the enzyme β-glucosidase and a boronic acid appended viologen together with a fluorescent reporter dye. β-Glucosidase degrades the cyanogenic glycoside amygdalin into hydrogen cyanide, glucose, and benzaldehyde. Only the released cyanide binds at the allosteric site of the receptor (boronic acid) thereby inducing changes in the affinity of a formerly bound fluorescent indicator dye at the other side of the receptor. Thus, the sensing probe performs as allosteric indicator displacement assay (AIDA) for cyanide in water. Interference studies with inorganic anions and glucose revealed that cyanide is solely responsible for the change in the fluorescent signal. DFT calculations on a model compound revealed a 1:1 binding ratio of the boronic acid and cyanide ion. The fluorescent enzyme assay for β-glucosidase uses amygdalin as natural substrate and allows measuring Michaelis-Menten kinetics in microtiter plates. The allosteric indicator displacement assay (AIDA) probe can also be used to detect cyanide traces in commercial amygdalin samples. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  4. Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.

    Science.gov (United States)

    Shi, Li-Shian; Kuo, Sheng-Chu; Sun, Han-Dong; Morris-Natschke, Susan L; Lee, Kuo-Hsiung; Wu, Tian-Shung

    2014-03-15

    Eight new cardiac glycosides/aglycones (antiaritoxiosides A-G, 1-7, and antiarotoxinin B, 8), two new coumarins (anticarins A-B, 41-42), and two new flavanones (antiarones L-K, 43-44) were isolated from trunk bark of Antiaris toxicaria together with 53 known compounds. The new structures were established by extensive analysis of spectroscopic data. Compound 1 (10-carboxy and 3α-hydroxy) and compounds 3-6 (10-hydroxy) contain unique substituents that are rarely found in cardiac glycosides. The cytotoxic effects of isolated compounds against ten human cancer cell lines, KB, KB-VIN, A549, MCF-7, U-87-MG, PC-3, 1A9, CAKI-1, HCT-9 and S-KMEL-2, were tested using the sulforhodamine B assay. Five compounds (12, 16, 20, 22, and 31) showed significant cytotoxicity against all ten cancer cell lines, with notable potency at the ng/mL level against some cell lines, which merits further development as clinical trial candidates. Copyright © 2014. Published by Elsevier Ltd.

  5. Combinations of Osmolytes, Including Monosaccharides, Disaccharides, and Sugar Alcohols Act in Concert During Cryopreservation to Improve Mesenchymal Stromal Cell Survival.

    Science.gov (United States)

    Pollock, Kathryn; Yu, Guanglin; Moller-Trane, Ralph; Koran, Marissa; Dosa, Peter I; McKenna, David H; Hubel, Allison

    2016-11-01

    glucose (a monosaccharide) for sucrose (a disaccharide) resulted in a significant drop in recovery. Taken together, the information from these studies increases our understanding of non-DMSO multicomponent cryoprotective solutions and the manner by which they enhance postthaw recovery.

  6. Merremins A-G, resin glycosides from Merremia hederacea with multidrug resistance reversal activity.

    Science.gov (United States)

    Wang, Wen-qiong; Song, Wei-bin; Lan, Xiao-jing; Huang, Min; Xuan, Li-jiang

    2014-10-24

    Five new pentasaccharide resin glycosides, named merremins A-E (1-5), two new pentasaccharide resin glycoside methyl esters, named merremins F and G (6, 7), and four known resin glycosides, murucoidin IV, murucoidin V, stoloniferin IV, and murucoidin XVII, were obtained from the aerial parts of Merremia hederacea. This is the first report of resin glycosides obtained from M. hederacea. In addition, the new compounds can be divided into three types: those possessing an 18-membered ring (1-4), compound 5 with a 20-membered ring, and those with an acyclic core (6, 7). Furthermore, the different types of resin glycosides were evaluated for their multidrug resistance reversal activities. Compounds 1, 5, 6, and murucoidin V were noncytotoxic and enhanced the cytotoxicity of vinblastine by 2.3-142.5-fold at 25 μM. Compound 5 and murucoidin V, with 20-membered rings, were more active than compound 1, with an 18-membered ring.

  7. Glycosidically bound volatiles as affected by ripening stages of Satsuma mandarin fruit.

    Science.gov (United States)

    Gao, Jie; Wu, Bo-Ping; Gao, Liu-Xiao; Liu, Hong-Ru; Zhang, Bo; Sun, Chong-De; Chen, Kun-Song

    2018-02-01

    Composition and changes in free volatiles have been extensively studied in citrus fruit such as mandarin. However, components of glycosidically bound volatiles and changes during fruit ripening have been rarely investigated. A total of 56 glycosidically-bound volatiles were identified in fruit peel at four ripening stages. The highest concentrations in glycosidically-bound volatiles were observed for methyl salicylate in ripening fruit. Concentration of total bound volatiles increased from color conversion stage at 150days after bloom (DAB), peaked at yellow stage (190DAB), followed by a decrease at orange stage (210DAB). Satsuma mandarin fruit at different ripening stages could be separated in a partial least squares-discriminant analysis (PLS-DA) plot using glycosidically bound volatiles as variables. In total 35 glycosidically bound volatiles were identified with variable importance in projection (VIP) score exceeding 1, which may be potential markers for separating fruit at different ripening stages. Copyright © 2017 Elsevier Ltd. All rights reserved.

  8. Stimulation of steviol glycoside accumulation in Stevia rebaudiana by red LED light.

    Science.gov (United States)

    Ceunen, Stijn; Werbrouck, Stefaan; Geuns, Jan M C

    2012-05-01

    The aim of this study was to determine whether steviol glycoside accumulation is under phytochrome control. The results indicate that Stevia rebaudiana Bertoni plants grown under short-day conditions showed precocious flowering and stagnation of steviol glycoside accumulation. Long night interruption by red LED light stimulated and sustained the vegetative growth as well as the accumulation of steviol glycosides in the leaves. After 7 weeks of treatment, steviol glycoside content was about two-fold higher in LED-treated plants than in the short-day control group. The effects of red LED light were measured both in a greenhouse and in a phytotron, irrespective of cultivar-specific differences. Therefore, it can be concluded that a mid-night interruption by red LED light during short photoperiods provides an easy and inexpensive method to increase vegetative leaf biomass production with an increased steviol glycoside yield. Copyright © 2012 Elsevier GmbH. All rights reserved.

  9. Mass spectrometric imaging of flavonoid glycosides and biflavonoids in Ginkgo biloba L.

    Science.gov (United States)

    Beck, Sebastian; Stengel, Julia

    2016-10-01

    Ginkgo biloba L. is known to be rich in flavonoids and flavonoid glycosides. However, the distribution within specific plant organs (e.g. within leaves) is not known. By using HPLC-MS and MS/MS we have identified a number of previously known G. biloba flavonoid glycosides and biflavonoids from leaves. Namely, kaempferol, quercetin, isorhamnetin, myricetin, laricitrin/mearnsetin and apigenin glycosides were identified. Furthermore, biflavonoids like ginkgetin/isoginkgetin were also detected. The application of MALDI mass spectrometric imaging, enabled the compilation of concentration profiles of flavonoid glycosides and biflavonoids in G. biloba L. leaves. Both, flavonoid glycosides and biflavonoids show a distinct distribution in leaf thin sections of G. biloba L. Copyright © 2016 Elsevier Ltd. All rights reserved.

  10. Synthesis of gold nanoparticles with glycosides: synthetic trends based on the structures of glycones and aglycones.

    Science.gov (United States)

    Jung, Jisung; Park, Suryeon; Hong, Suckchang; Ha, Min Woo; Park, Hyeung-geun; Park, Youmie; Lee, Hyo-Jong; Park, Yohan

    2014-03-11

    A new, room temperature synthetic method for gold nanoparticles from auric acid with glycosides as reducing agents in aqueous NaOH is presented. As a mechanistic study of the oxidation sites on the glycosides, eight sugar-containing reductants (glycoside, glucose, glucuronic acid) have been tested in the synthesis of gold nanoparticles to determine their trends based on the structures of glycones and aglycones. As a result of the comparison among the eight sugar-containing reductants, it was determined that C-6 of glycosides is oxidized to a carboxylic acid during the reduction of auric acid. To detect the oxidized compounds of the glycosides, the reaction mixtures were monitored by (13)C NMR. Among the eight sugar-containing reductants, phenyl β-D-glucoside generated the highest synthetic yield of mono-dispersed, round gold nanoparticles (13.15±1.30 nm, 99.7% yield). Copyright © 2013 Elsevier Ltd. All rights reserved.

  11. Quantitation of sweet steviol glycosides by means of a HILIC-MS/MS-SIDA approach.

    Science.gov (United States)

    Well, Caroline; Frank, Oliver; Hofmann, Thomas

    2013-11-27

    Meeting the rising consumer demand for natural food ingredients, steviol glycosides, the sweet principle of Stevia rebaudiana Bertoni (Bertoni), have recently been approved as food additives in the European Union. As regulatory constraints require sensitive methods to analyze the sweet-tasting steviol glycosides in foods and beverages, a HILIC-MS/MS method was developed enabling the accurate and reliable quantitation of the major steviol glycosides stevioside, rebaudiosides A-F, steviolbioside, rubusoside, and dulcoside A by using the corresponding deuterated 16,17-dihydrosteviol glycosides as suitable internal standards. This quantitation not only enables the analysis of the individual steviol glycosides in foods and beverages but also can support the optimization of breeding and postharvest downstream processing of Stevia plants to produce preferentially sweet and least bitter tasting Stevia extracts.

  12. Thermodynamics of the interaction of RbCl with some monosaccharides (D-glucose, D-galactose, D-xylose, and D-arabinose) in aqueous solutions at 298.15K.

    Science.gov (United States)

    Jiang, Yucheng; Hu, Mancheng; Li, Shuni; Wang, Jianji; Zhuo, Kelei

    2006-02-06

    The Gibbs energy interaction parameters of RbCl with some monosaccharides (D-glucose, D-galactose, D-xylose, and D-arabinose) in water, g(ES), were obtained from electromotive force (emf) measurements of the electrochemical cell without liquid junction and containing two ion-selective electrodes (ISE): K-ISEmid R:RbCl(m(E))mid R:ISE-Cl and K-ISEmid R:RbCl(m(E)),saccharide (m(S))mid R:ISE-Cl, at 298.15K. The enthalpy interaction parameters of RbCl with these monosaccharides in water, h(ES), are determined according to the McMillan-Mayer theory from the measurements of the enthalpies of mixing of aqueous RbCl solutions with aqueous monosaccharide solutions, as well as the enthalpies of dilution of RbCl and monosaccharide solutions in pure water at 298.15K by a calorimetric method. Furthermore, the entropy interaction parameters, s(ES), can be evaluated through g(ES) and h(ES). The results suggest that the electrostatic interactions of these monosaccharides with RbCl in water are predominant compared with structural interactions, and these parameters are controlled primarily by the stereochemical structure of the monosaccharides in water.

  13. Pharmacokinetics and bioavailability of quercetin glycosides in humans.

    Science.gov (United States)

    Graefe, E U; Wittig, J; Mueller, S; Riethling, A K; Uehleke, B; Drewelow, B; Pforte, H; Jacobasch, G; Derendorf, H; Veit, M

    2001-05-01

    Due to its potentially beneficial impact on human health, the polyphenol quercetin has come into the focus of medicinal interest. However, data on the bioavailability of quercetin after oral intake are scarce and contradictory. Previous investigations indicate that the disposition of quercetin may depend on the sugar moiety of the glycoside or the plant matrix. To determine the influence of the sugar moiety or matrix on the absorption of quercetin, two isolated quercetin glycosides and two plant extracts were administered to 12 healthy volunteers in a four-way crossover study. Each subject received an onion supplement or quercetin-4'-O-glucoside (both equivalent to 100 mg quercetin), as well as quercetin-3-O-rutinoside and buckwheat tea (both equivalent to 200 mg quercetin). Samples were analyzed by HPLC with a 12-channel coulometric array detector. In human plasma, only quercetin glucuronides, but no free quercetin, could be detected. There was no significant difference in the bioavailability and pharmacokinetic parameters between the onion supplement and quercetin-4'-O-glucoside. Peak plasma concentrations were 2.3 +/- 1.5 microg x mL(-1) and 2.1 +/- 1.6 microg x mL(-1) (mean +/- SD) and were reached after 0.7 +/- 0.2 hours and 0.7 +/- 0.3 hours, respectively. After administration of buckwheat tea and rutin, however, peak plasma levels were--despite the higher dose-only 0.6 +/- 0.7 microg x mL(-1) and 0.3 +/- 0.3 microg x mL(-1), respectively. Peak concentrations were reached 4.3 +/- 1.8 hours after administration of buckwheat tea and 7.0 +/- 2.9 hours after ingestion of rutin. The terminal elimination half-life was about 11 hours for all treatments. Thus, the disposition of quercetin in humans primarily depends on the sugar moiety. To a minor extent, the plant matrix influences both the rate and extent of absorption in the case of buckwheat tea administration compared with the isolated compound. The site of absorption seems to be different for quercetin-4'-O

  14. Biosynthesis and regulation of cyanogenic glycoside production in forage plants.

    Science.gov (United States)

    Sun, Zhanmin; Zhang, Kaixuan; Chen, Cheng; Wu, Yanmin; Tang, Yixiong; Georgiev, Milen I; Zhang, Xinquan; Lin, Min; Zhou, Meiliang

    2017-10-12

    The natural products cyanogenic glycosides (CNglcs) are present in various forage plant species including Sorghum spp., Trifolium spp., and Lotus spp. The release of toxic hydrogen cyanide (HCN) from endogenous CNglcs, which is known as cyanogenesis, leads to a serious problem for animal consumption while as defensive secondary metabolites, CNglcs play multiple roles in plant development and responses to adverse environment. Therefore, it is highly important to fully uncover the molecular mechanisms of CNglc biosynthesis and regulation to manipulate the contents of CNglcs in forage plants for fine-tuning the balance between defensive responses and food safety. This review summarizes recent studies on the production, function, polymorphism, and regulation of CNglcs in forage plants, aiming to provide updated knowledge on the ways to manipulate CNglcs for further beneficial economic effects.

  15. Phenylethanoid Glycosides of Cistanche on menopausal syndrome model in mice

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    Shuo Tian

    2017-05-01

    Full Text Available Cistanche is the traditional and precious Chinese herbal, with two thousand years of use history in China. It has the effect on tonifying kidney, strong supplement to the liver and kidney, and replenishing essence and blood, known as the “desert ginseng”. Here, we explored the mechanism of Phenylethanoid Glycosides of Cistanche (PGC to the model mice of menopausal syndrome, as well as the therapeutic effect and characteristics of PGC to the menopausal syndrome. In this study, KM mice were reproduced by the complete resection of the ovaries on both sides of the back to establish the model mice of menopausal syndrome (MPS, and received distilled water or drugs, respectively. Model mice received distilled water. Mice received 200 mg/(kg day high doses of Phenylethanoid Glycosides of Cistanche (HPGC, and 100 mg/(kg day medium doses of Phenylethanoid Glycosides of Cistanche (MPGC, and 50 mg/(kg day low doses of Phenylethanoid Glycosides of Cistanche (LPGC. After 21 days, it could determine the number of independent activities and the number of standing, the latent period of first entering the dark room, and the electric number. It also calculated the viscera index of uterus, thymus, spleen, measured the levels of estradiol (E2, testosterone (T, luteinizing hormone (LH, and follicle-stimulating hormone (FSH in the serum. Furthermore, it observed the pathological changes of uterus, thymus, spleen and pituitary of mice. The results showed that behavioral indicators: Compared with the model group (MG, HPGC, MPGC, LPGC could increase the independent activities (P < 0.01; HPGC, MPGC could increase the number of standing, the latent period of first entering the dark room, and reduce the electric number (P < 0.01; LPGC could increase the number of standing (P < 0.05; Viscera index: Compared with MG, HPGC, MPGC could increase the viscera index of uterus, thymus, spleen (P < 0.01; LPGC could increase the viscera index of uterus (P < 0

  16. A New Acylated Flavonol Glycoside from Chenopodium foliosum

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    Zlatina Kokanova-Nedialkova, , , , , and

    2014-07-01

    Full Text Available A new acylated flavonol glycoside, namely gomphrenol-3-O-( 5 '''-O-E-feruloyl-β-D-apiofuranosyl-(1→2[β-D-glucopyranosyl-(1→6]-β-D-glucopyranoside (1 was isolated from the aerial parts of Chenopodium foliosum Asch. The structure of 1 was determined by means of spectroscopic methods (1D and 2D NMR, UV, IR, and HRESIMS. Radical scavenging and antioxidant activities of 1 were established using DPPH and ABTS radicals, FRAP assay and inhibition of lipid peroxidation (LP in linoleic acid system by the ferric thiocyanate method. Compound 1 showed low activity (DPPH and ABTS or lack of activity (FRAP and LP. In combination with CCl 4, 1 reduced the damage caused by the hepatotoxic agent and preserved cell viability and GSH level, decreased LDH leakage and reduced lipid damage. Effects were concentration dependent, most visible at the highest concentration (100 µg/m L , and similar to those of silymarin .

  17. Four New Flavonol Glycosides from the Leaves of Brugmansia suaveolens

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    Fabiana Geller

    2014-05-01

    Full Text Available Four new flavonol glycosides were isolated from the leaves of Brugmansia suaveolens: kaempferol 3-O-β-D-glucopyranosyl-(1'''→2''-O-α-L-arabinopyranoside (1, kaempferol 3-O-β-D-glucopyranosyl-(1'''→2''-O-α-L-arabinopyranoside-7-O-į-D-gluco-pyranoside (2, kaempferol 3-O-β-D-[6'''-O-(E-caffeoyl]-glucopyranosyl-(1'''→2''-O-α-l-arabinopyranoside-7-O-β-D-glucopyranoside (3, and kaempferol 3-O-β-D-[2'''-O-(E-caffeoyl]-glucopyranosyl-(1'''→2''-O-α-l-arabinopyranoside-7-O-β-D-glucopyranoside (4. The structure elucidation was performed by MS, 1D and 2D NMR analyses.

  18. Pentasaccharide resin glycosides from Ipomoea cairica and their cytotoxic activities.

    Science.gov (United States)

    Yu, Bangwei; Luo, Jianguang; Wang, Junsong; Zhang, Dongming; Yu, Shishan; Kong, Lingyi

    2013-11-01

    Six partially acylated pentasaccharide resin glycosides, cairicosides A-F, were isolated from the aerial parts of Ipomoea cairica. These compounds were characterized as a group of macrolactones of simonic acid A, partially acylated with different organic acids. The lactonization site of 11S-hydroxyhexadecanoic acid (jalapinolic acid) was bound to the second saccharide moiety at C-3 in cairicosides A-E, while at C-2 in cairicoside F. Structures were established by spectroscopic and chemical methods. Compounds cairicosides A-E exhibited moderate cytotoxicity against a small panel of human tumor cell lines with IC50 values in the range of 4.28-14.31μM. Copyright © 2013 Elsevier Ltd. All rights reserved.

  19. Antioxidant phenolic glycoside and flavonoids from Pieris japonica.

    Science.gov (United States)

    Li, Yan-Ping; Li, Yan-Hong; Zhong, Jin-Dong; Li, Rong-Tao

    2013-01-01

    A new phenolic glycoside, benzyl 2-hydroxy-4-O-β-D-glucopyranosyl-benzoate (1), along with nine known flavonoids, epicatechin-(2 → O → 7,4 → 8)-ent-epicatechin (2), bis-8,8'-catechinylmethane (3), quercetin (4), quercetin-3-O-α-L-arabinfuranoside (5), quercetin-3-O-α-L-rhamnopyranoside (6), astilbin (7), engeletin (8), (2S,3R)-ent-catechin (9), and 2',4-dihydroxy-4'-methoxy-6'-O-β-D-glucopyranosyl dihydrochalcone (10), was isolated from the flowers of Pieris japonica. Their structures were elucidated on the basis of MS, 1D NMR, and 2D NMR techniques. This paper describes the isolation, structural elucidation as well as in vitro antioxidant activity of these compounds.

  20. Potential hypoglycaemic activity phenolic glycosides from Moringa oleifera seeds.

    Science.gov (United States)

    Wang, Fang; Zhong, Huan-Huan; Chen, Wei-Ke; Liu, Qing-Pu; Li, Cun-Yu; Zheng, Yun-Feng; Peng, Guo-Ping

    2017-08-01

    Moringa oleifera seed has remarkable curative effects on reducing blood pressure, blood sugar and enhancing human immunity. In this study, one novel phenolic glycoside (1) together with four known compounds 2-5 were isolated from the macroporous resin adsorption extract of M. oleifera seeds, and the compound 3 was reported for the first time from this plant. The structure of the new crystalline compound was determined on the basis of spectroscopic analyses including mass spectrometry, 1D and 2D NMR experiments. The hypoglycaemic activity of isolated compounds was investigated with HepG2 cell and STZ-induced mice. It was found that compound 1, 4 and 5 could promote the glucose consumption of insulin resistance cells and reduce blood glucose levels of STZ-induced mice. This study concludes that compound 1, 4 and 5 may be developed as new and safe hypoglycaemic drugs.

  1. Antioxidant phenylethanoid glycosides and a neolignan from Jacaranda caucana.

    Science.gov (United States)

    Martin, Frédéric; Hay, Anne-Emmanuelle; Quinteros Condoretty, Valentin R; Cressend, Delphine; Reist, Marianne; Gupta, Mahabir P; Carrupt, Pierre-Alain; Hostettmann, Kurt

    2009-05-22

    Extracts from several plants of the family Bignoniaceae from Panama were submitted to a rapid DPPH TLC test for the detection of radical-scavenging activity. The MeOH extract of the stems of Jacaranda caucana, a tree that grows from Costa Rica to Colombia, was selected due to its interesting activity and the lack of phytochemical studies on the polar extract. This extract was partitioned between ethyl acetate, butanol, and water. The EtOAc fraction afforded two new phenylethanoid glycosides (1, 2), along with protocatechuic acid, acteoside, and jionoside D. Further purifications yielded isoacteoside and martynoside. The BuOH fraction afforded a new rhamnosyl derivative of sisymbrifolin (8), a neolignan. The structures were determined by means of spectrometric methods, including 1D and 2D NMR experiments and MS analysis.

  2. Platinum and vanadate Bioactive Complexes of Glycoside Naringin and Phenolates

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    Fazary Ahmed E.

    2017-08-01

    Full Text Available Platinum(II and vanadium(V solid binary and ternary complexes involving naringin, a flavanone glycoside in found in grapefruit, and some phenolic acids were synthesized and fully characterized using detailed structural and spectroscopic analysis techniques such as IR, NMR, and SEM techniques. The magnetic susceptibility results as well line drawings of the platinum and vanadium complexes showed four-coordinate square-planar and remarkable low-spin diamagnetic species; which is in agreement with the structures proposed. The cytotoxic activities of the binary and ternary vanadium and platinum metal complexes of phenolic acids and naringin were tested and evaluated against HepG2 (human hepatocellular carcinoma, MCF-7 (human breast adenocarcinoma, and HCT116 (human colorectal carcinoma tumor cell lines. Also, their antioxidant activities were examined by free radical scavenging assay. The relationship between the chemical structure of the synthesized complexes and their biological influence was studied and evaluated.

  3. A new antibacterial benzophenone glycoside from Psidium guajava (Linn.) leaves.

    Science.gov (United States)

    Ukwueze, Stanley E; Osadebe, Patience O; Okoye, Festus B C

    2015-01-01

    Bioactivity-guided fractionation of methanol extract from the leaves of Psidium guajava L. (Myrtaceae) yielded a new benzophenone glycoside, Guajaphenone A (2) together with two known compounds, Garcimangosone D (1) and Guaijaverin (3). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and electrospray ionisation mass spectrometry (ESI-MS). The isolated compounds were screened against standard strains of Gram-positive and Gram-negative bacteria using broth dilution assay method, and the MIC values determined and compared with reference antibiotic ceftriaxone. They were found to have significant antibacterial activities against Escherichia coli and Staphylococcus aureus with all of them showing better activities against S. aureus, but displaying weaker activities, in comparison to ceftriaxone. However, despite reduced effect of these compounds against the organisms, this work opens the perspective to use these molecules as 'leads' for the design of novel and selective drug candidates for some tropical infectious diseases.

  4. Iridoid glycosides and polyphenolic compounds from Teucrium chamaedrys L.

    Science.gov (United States)

    Frezza, Claudio; Venditti, Alessandro; Matrone, Giorgia; Serafini, Ilaria; Foddai, Sebastiano; Bianco, Armandodoriano; Serafini, Mauro

    2017-10-23

    In this work, the phytochemical analysis of Teucrium chamaedrys L. collected in Italy was reported. Eight compounds were isolated and identified by means of classical column chromatography and spectroscopic techniques, such as NMR and MS. In detail, these compounds were: verbascoside (1), forsythoside b (2), samioside (3), alyssonoside (4), harpagide (5), 8-O-acetyl-harpagide (6), cirsiliol (7) and β-arbutin (8). The presence of these compounds, in particular iridoids and phenyl-ethanoid glycosides, has a chemotaxonomic relevance and results to be in perfect accordance with the current botanical classification of the species. In addition, it provides a phytochemical rationale for the use of this particular plant in the ethno-pharmacological field. Conversely, it is worth of mention the absence of potentially toxic components, unlike to what observed in other species of the genus which can no longer be used for ethno-medicinal purposes.

  5. Glycosides from Stevia rebaudiana Bertoni Possess Insulin-Mimetic and Antioxidant Activities in Rat Cardiac Fibroblasts.

    Science.gov (United States)

    Prata, Cecilia; Zambonin, Laura; Rizzo, Benedetta; Maraldi, Tullia; Angeloni, Cristina; Vieceli Dalla Sega, Francesco; Fiorentini, Diana; Hrelia, Silvana

    2017-01-01

    Stevia rebaudiana Bertoni is a shrub having a high content of sweet diterpenoid glycosides in its leaves, mainly stevioside and rebaudioside A, which are used as noncaloric, natural sweeteners. The aim of this study was to deepen the knowledge about the insulin-mimetic effect exerted by four different mixtures of steviol glycosides, rich in stevioside and rebaudioside A, in neonatal rat cardiac fibroblasts. The potential antioxidant activity of these steviol glycosides was also assessed, as oxidative stress is associated with diabetes. Likewise the insulin effect, steviol glycosides caused an increase in glucose uptake into rat fibroblasts by activating the PI3K/Akt pathway, thus inducing Glut4 translocation to the plasma membrane. The presence of S961, an insulin antagonist, completely abolished these effects, allowing to hypothesize that steviol glycosides could act as ligands of the same receptor engaged by insulin. Moreover, steviol glycosides counteracted oxidative stress by increasing reduced glutathione intracellular levels and upregulating expression and activity of the two antioxidant enzymes superoxide dismutase and catalase. The present work unravels the insulin-mimetic effect and the antioxidant property exerted by steviol glycosides, suggesting their potential beneficial role in the cotreatment of diabetes and in health maintenance.

  6. Glycosides from Stevia rebaudiana Bertoni Possess Insulin-Mimetic and Antioxidant Activities in Rat Cardiac Fibroblasts

    Science.gov (United States)

    Prata, Cecilia; Zambonin, Laura; Rizzo, Benedetta; Vieceli Dalla Sega, Francesco

    2017-01-01

    Stevia rebaudiana Bertoni is a shrub having a high content of sweet diterpenoid glycosides in its leaves, mainly stevioside and rebaudioside A, which are used as noncaloric, natural sweeteners. The aim of this study was to deepen the knowledge about the insulin-mimetic effect exerted by four different mixtures of steviol glycosides, rich in stevioside and rebaudioside A, in neonatal rat cardiac fibroblasts. The potential antioxidant activity of these steviol glycosides was also assessed, as oxidative stress is associated with diabetes. Likewise the insulin effect, steviol glycosides caused an increase in glucose uptake into rat fibroblasts by activating the PI3K/Akt pathway, thus inducing Glut4 translocation to the plasma membrane. The presence of S961, an insulin antagonist, completely abolished these effects, allowing to hypothesize that steviol glycosides could act as ligands of the same receptor engaged by insulin. Moreover, steviol glycosides counteracted oxidative stress by increasing reduced glutathione intracellular levels and upregulating expression and activity of the two antioxidant enzymes superoxide dismutase and catalase. The present work unravels the insulin-mimetic effect and the antioxidant property exerted by steviol glycosides, suggesting their potential beneficial role in the cotreatment of diabetes and in health maintenance. PMID:28947927

  7. Quantification of flavonol glycosides in Camellia sinensis by MRM mode of UPLC-QQQ-MS/MS.

    Science.gov (United States)

    Wu, Yahui; Jiang, Xiaolan; Zhang, Shuxiang; Dai, Xinlong; Liu, Yajun; Tan, Huarong; Gao, Liping; Xia, Tao

    2016-04-01

    Phenolic compounds are major components of tea flavour, in which catechins and flavonol glycosides play important roles in the astringent taste of tea infusion. However, the flavonol glycosides are difficult to quantify because of the large variety, as well as the inefficient seperation on chromatography. In this paper, a total of 15 flavonol glycosides in the tea plant (Camellia sinensis) were identified by the high performance liquid chromatography (HPLC) coupled to a time-of-flight mass spectrometer (TOF-MS), and a quantitative method was established based on multiple reaction monitoring (MRM) mode of ultra-high performance liquid chromatography (UPLC) coupled to a triple quadrupole mass spectrometer (QQQ-MS/MS). It provided the limit of detection and quantification to the order of picogram, which was more sensitive than the HPLC detection of the order of nanogram. The relative standard deviations of the intra- and inter-day variations in retention time and signal intensity (peak area) of six analytes were less than 0.26% and 4%, respectively. The flavonol glycosides of four tea cultivars were relatively quantified using the signal intensity (peak area) of product ion, in which six flavonol glycosides were quantified by the authentic standards. The results showed that the flavonol mono-, di- and tri-glycoside mostly accumulated in young leaves of the four tea cultivars. Notably, the myricetin 3-O-galactoside was the major component among the six flavonol glycosides detected. Copyright © 2016 Elsevier B.V. All rights reserved.

  8. Glycosides from Stevia rebaudiana Bertoni Possess Insulin-Mimetic and Antioxidant Activities in Rat Cardiac Fibroblasts

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    Cecilia Prata

    2017-01-01

    Full Text Available Stevia rebaudiana Bertoni is a shrub having a high content of sweet diterpenoid glycosides in its leaves, mainly stevioside and rebaudioside A, which are used as noncaloric, natural sweeteners. The aim of this study was to deepen the knowledge about the insulin-mimetic effect exerted by four different mixtures of steviol glycosides, rich in stevioside and rebaudioside A, in neonatal rat cardiac fibroblasts. The potential antioxidant activity of these steviol glycosides was also assessed, as oxidative stress is associated with diabetes. Likewise the insulin effect, steviol glycosides caused an increase in glucose uptake into rat fibroblasts by activating the PI3K/Akt pathway, thus inducing Glut4 translocation to the plasma membrane. The presence of S961, an insulin antagonist, completely abolished these effects, allowing to hypothesize that steviol glycosides could act as ligands of the same receptor engaged by insulin. Moreover, steviol glycosides counteracted oxidative stress by increasing reduced glutathione intracellular levels and upregulating expression and activity of the two antioxidant enzymes superoxide dismutase and catalase. The present work unravels the insulin-mimetic effect and the antioxidant property exerted by steviol glycosides, suggesting their potential beneficial role in the cotreatment of diabetes and in health maintenance.

  9. Consumption of a low fermentable Oligo-, Di-, Mono-saccharides, and polyols diet and irritable bowel syndrome: A systematic review

    Directory of Open Access Journals (Sweden)

    Helia Pourmand

    2017-01-01

    Full Text Available Consumption of low dietary fermentable carbohydrates, including fermentable oligo-, di-, mono-saccharides, and polyols (FODMAP has been hypothesized to improve symptoms of irritable bowel syndrome (IBS. This study was done to summarize findings from earlier evidence on the effect of a low FODMAP diet (LFD on the symptoms of IBS. We searched in ISI Web of Knowledge, PubMed, Scopus, and Google Scholar using the following keywords: “FODMAP” OR “oligosaccharides” OR “disaccharides” OR “Monosaccharaides” in combination with “irritable bowel syndrome” or “IBS” or “Gastrointestinal Disease.” The reference lists of the relevant papers were also examined to avoid missing any publication. No time and language restrictions were applied. The relevant studies were selected through an independent search by two investigators. Overall, 778 relevant articles were found in our initial search. After reviewing title and abstracts, 763 papers were excluded from this review and 15 studies were included. All published studies were interventional studies in which patients with IBS had been recommended or randomized to receive a LFD. Three studies had quasi-experimental design, 9 were parallel randomized clinical trial and 3 studies were of randomized cross-over trials. These studies were conducted between 2009 and 2016. Nine studies were done in Europe, 2 in US, 3 in Australia, and one in Asia. Sample sizes of these studies were varied from 12 to 182. All studies had been conducted on both sexes, with the majority of participants as women (>70%. The age range was between 11 and 74 years in different studies. One study was performed on children, 9 on adults, and 5 others were in young-to-middle age groups. Duration of intervention was varied from 2 days to 16 months (2 studies with <1 week, and others with more than 2 weeks. Eight studies had suggested a significant effect of LFD on the improvement of all IBS symptoms, and 1 study had

  10. The monosaccharide transporter gene family in land plants is ancient and shows differential subfamily expression and expansion across lineages

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    Thomas Michael A

    2006-08-01

    Full Text Available Abstract Background In plants, tandem, segmental and whole-genome duplications are prevalent, resulting in large numbers of duplicate loci. Recent studies suggest that duplicate genes diverge predominantly through the partitioning of expression and that breadth of gene expression is related to the rate of gene duplication and protein sequence evolution. Here, we utilize expressed sequence tag (EST data to study gene duplication and expression patterns in the monosaccharide transporter (MST gene family across the land plants. In Arabidopsis, there are 53 MST genes that form seven distinct subfamilies. We created profile hidden Markov models of each subfamily and searched EST databases representing diverse land plant lineages to address the following questions: 1 Are homologs of each Arabidopsis subfamily present in the earliest land plants? 2 Do expression patterns among subfamilies and individual genes within subfamilies differ across lineages? 3 Has gene duplication within each lineage resulted in lineage-specific expansion patterns? We also looked for correlations between relative EST database representation in Arabidopsis and similarity to orthologs in early lineages. Results Homologs of all seven MST subfamilies were present in land plants at least 400 million years ago. Subfamily expression levels vary across lineages with greater relative expression of the STP, ERD6-like, INT and PLT subfamilies in the vascular plants. In the large EST databases of the moss, gymnosperm, monocot and eudicot lineages, EST contig construction reveals that MST subfamilies have experienced lineage-specific expansions. Large subfamily expansions appear to be due to multiple gene duplications arising from single ancestral genes. In Arabidopsis, one or a few genes within most subfamilies have much higher EST database representation than others. Most highly represented (broadly expressed genes in Arabidopsis have best match orthologs in early divergent lineages

  11. Agrobacterium Mediated Transient Gene Silencing (AMTS) in Stevia rebaudiana: Insights into Steviol Glycoside Biosynthesis Pathway

    Science.gov (United States)

    Guleria, Praveen; Yadav, Sudesh Kumar

    2013-01-01

    Background Steviol glycoside biosynthesis pathway has emerged as bifurcation from ent-kaurenoic acid, substrate of methyl erythritol phosphate pathway that also leads to gibberellin biosynthesis. However, the genetic regulation of steviol glycoside biosynthesis has not been studied. So, in present study RNA interference (RNAi) based Agrobacterium mediated transient gene silencing (AMTS) approach was followed. SrKA13H and three SrUGTs (SrUGT85C2, SrUGT74G1 and SrUGT76G1) genes encoding ent-kaurenoic acid-13 hydroxylase and three UDP glycosyltransferases of steviol glycoside biosynthesis pathway were silenced in Stevia rebaudiana to understand its molecular mechanism and association with gibberellins. Methodology/Principal Findings RNAi mediated AMTS of SrKA13H and three SrUGTs has significantly reduced the expression of targeted endogenous genes as well as total steviol glycoside accumulation. While gibberellins (GA3) content was significantly enhanced on AMTS of SrUGT85C2 and SrKA13H. Silencing of SrKA13H and SrUGT85C2 was found to block the metabolite flux of steviol glycoside pathway and shifted it towards GA3 biosynthesis. Further, molecular docking of three SrUGT proteins has documented highest affinity of SrUGT76G1 for the substrates of alternate pathways synthesizing steviol glycosides. This could be a plausible reason for maximum reduction in steviol glycoside content on silencing of SrUGT76G1 than other genes. Conclusions SrKA13H and SrUGT85C2 were identified as regulatory genes influencing carbon flux between steviol glycoside and gibberellin biosynthesis. This study has also documented the existence of alternate steviol glycoside biosynthesis route. PMID:24023961

  12. Agrobacterium mediated transient gene silencing (AMTS in Stevia rebaudiana: insights into steviol glycoside biosynthesis pathway.

    Directory of Open Access Journals (Sweden)

    Praveen Guleria

    Full Text Available BACKGROUND: Steviol glycoside biosynthesis pathway has emerged as bifurcation from ent-kaurenoic acid, substrate of methyl erythritol phosphate pathway that also leads to gibberellin biosynthesis. However, the genetic regulation of steviol glycoside biosynthesis has not been studied. So, in present study RNA interference (RNAi based Agrobacterium mediated transient gene silencing (AMTS approach was followed. SrKA13H and three SrUGTs (SrUGT85C2, SrUGT74G1 and SrUGT76G1 genes encoding ent-kaurenoic acid-13 hydroxylase and three UDP glycosyltransferases of steviol glycoside biosynthesis pathway were silenced in Stevia rebaudiana to understand its molecular mechanism and association with gibberellins. METHODOLOGY/PRINCIPAL FINDINGS: RNAi mediated AMTS of SrKA13H and three SrUGTs has significantly reduced the expression of targeted endogenous genes as well as total steviol glycoside accumulation. While gibberellins (GA3 content was significantly enhanced on AMTS of SrUGT85C2 and SrKA13H. Silencing of SrKA13H and SrUGT85C2 was found to block the metabolite flux of steviol glycoside pathway and shifted it towards GA3 biosynthesis. Further, molecular docking of three SrUGT proteins has documented highest affinity of SrUGT76G1 for the substrates of alternate pathways synthesizing steviol glycosides. This could be a plausible reason for maximum reduction in steviol glycoside content on silencing of SrUGT76G1 than other genes. CONCLUSIONS: SrKA13H and SrUGT85C2 were identified as regulatory genes influencing carbon flux between steviol glycoside and gibberellin biosynthesis. This study has also documented the existence of alternate steviol glycoside biosynthesis route.

  13. The effect of irradiation on the intracellular transportation of the parotid gland acinar cells in the mouse. Localization of monosaccharides studied by electron microscopic autoradiography

    Energy Technology Data Exchange (ETDEWEB)

    Matsunaga, Hajime (Nippon Dental Univ., Tokyo (Japan))

    1994-06-01

    The present study was designed to investigate the effects of radiation on the ability to ingest monosaccharides and intracellular transportation in the parotid gland in mice. The submandibular regions, including the parotid gland, was exposed to 10 Gy of X-rays. Three days after irradiation, the localization of reducing silver grains in organelles was determined, using electron microscopic autoradiography with H-3 labeled galactosamine, glucosamine, fucose, and mannose. In the non-irradiated group, the proportion of reducing silver grains in the acinar cells began to increase 15 min after administration of monosaccharides, reached a peak at 180 min, and thereafter decreased. Similar findings were observed in the irradiated group, although the values were lower than the non-irradiated group. The proportion of reducing silver grains in the endoplasmic reticulum reached a peak at 15 min in both the non-irradiated and irradiated groups, and gradually decreased until 120 min. Thereafter, it became almost constant and low, but the proportion in the irradiated group was slightly higher than in the non-irradiated group. The proportion of reducing silver grains in the Golgi apparatus was maximum at 60 min in the non-irradiated group, and gradually decreased until 360 min. A similar tendency was seen in the irradiated group, although its variation was not so marked as in the non-irradiated group. The proportion of reducing silver grains in the condensing vacuoles was maximum at 120 min, and thereafter, it decreased; the decrease was only slight in the irradiated group. The proportion of reducing silver grains in secretory granules increased with time in both the non-irradiated and irradiated groups, although this was only slight in the irradiated group, and reached a peak at 360 min. Transportation of monosaccharides in an acinar cell was found to be delayed by irradiation. (N.K.).

  14. Crypthophilic acids A, B, and C: resin glycosides from aerial parts of Scrophularia crypthophila.

    Science.gov (United States)

    Caliş, Ihsan; Sezgin, Yükselen; Dönmez, Ali A; Rüedi, Peter; Tasdemir, Deniz

    2007-01-01

    The water-soluble part of the methanolic extract from the aerial parts of Scrophularia crypthophila, through chromatographic methods, yielded three new resin glycosides, crypthophilic acids A - C (1-3). Compounds 1-3 are tetraglycosides of (+)-3S,12S-dihydroxypalmitic acid. The structures of these and 10 known compounds were elucidated by spectroscopic and chemical means. All natural resin glycosides known so far have been obtained from Convolvulaceae plants; this is the first report of such glycosides from another, taxonomically unrelated family (Scrophulariaceae).

  15. Allimacrosides A-E, new steroidal glycosides from Allium macrostemon Bunge.

    Science.gov (United States)

    Kim, Yun Sik; Suh, Won Se; Park, Kyoung Jin; Choi, Sang Un; Lee, Kang Ro

    2017-02-01

    A new pregnane-type steroidal glycoside (1), two new spirostane-type steroidal glycosides (2, 3), and two new furostane-type steroidal glycosides (4, 5), named allimacrosides A-E, together with four known compounds (6-9) were isolated from a 80% MeOH extract of Allium macrostemon Bunge. The identification and structural elucidation of these compounds were based on their 1D- and 2D-NMR spectra, and HR-FAB-MS data analysis. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using the sulforhodamine B bioassay. Copyright © 2016 Elsevier Inc. All rights reserved.

  16. Synthesis and Sensory Evaluation of ent-Kaurane Diterpene Glycosides

    Directory of Open Access Journals (Sweden)

    Venkata Sai Prakash Chaturvedula

    2012-07-01

    Full Text Available Catalytic hydrogenation of the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana, namely rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH2 and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data and chemical studies. Also, we report herewith the sensory evaluation of all the reduced compounds against their corresponding original steviol glycosides and sucrose for the sweetness property of these molecules.

  17. Variation of quercetin glycoside derivatives in three onion (Allium cepa L.) varieties

    OpenAIRE

    Kwak, Jung-Ho; Seo, Jeong Min; Kim, Na-Hyung; Arasu, Mariadhas Valan; Kim, Sunggil; Yoon, Moo Kyoung; Kim, Sun-Ju

    2016-01-01

    The aim of this study was to quantify the contents of individual quercetin glycosides in red, yellow and chartreuse onion by High Performance Liquid Chromatography (HPLC) analysis. Acid hydrolysis of individual quercetin glycosides using 6 M hydrochloric acid guided to identify and separate quercetin 7,4′-diglucoside, quercetin 3-glucoside, quercetin 4′-glucoside, and quercetin. The contents of total quercetin glycosides varied extensively among three varieties (ranged from 16.10 to 103.93 mg...

  18. A remote but significant sequence homology between glycoside hydrolase clan GH-H and glycoside hydrolase family GH 31

    DEFF Research Database (Denmark)

    Janecek, S.; Svensson, Birte; MacGregor, E.A.

    2007-01-01

    Although both the α-amylase super-family, i.e. the glycoside hydrolase (GH) clan GH-H (the GH families 13, 70 and 77), and family GH31 share some characteristics, their different catalytic machinery prevents classification of GH31 in clan GH-H. A significant but remote evolutionary relatedness is......7 and β8 of the GH-H and GH31 (β/α)8-barrels. Structure comparison of GH13 α-amylase and GH31 α-xylosidase guided alignment of GH-H and GH31 members for construction of evolutionary trees. The closest sequence relationship displayed by GH31 is to GH77 of clan GH-H....

  19. Ultrasonication-Assisted Solvent Extraction of Quercetin Glycosides from ‘Idared’ Apple Peels

    Directory of Open Access Journals (Sweden)

    Gwendolyn M. Huber

    2011-11-01

    Full Text Available Quercetin and quercetin glycosides are physiologically active flavonol molecules that have been attributed numerous health benefits. Recovery of such molecules from plant matrices depends on a variety of factors including polarity of the extraction solvent. Among the solvents of a wide range of dielectric constants, methanol recovered the most quercetin and its glycosides from dehydrated ‘Idared’ apple peels. When ultra-sonication was employed to facilitate the extraction, exposure of 15 min of ultrasound wavelengths of dehydrated apple peel powder in 80% to 100% (v/v methanol in 1:50 (w:v solid to solvent ratio provided the optimum extraction conditions for quercetin and its glycosides. Acidification of extraction solvent with 0.1% (v/v or higher concentrations of HCl led to hydrolysis of naturally occurring quercetin glycosides into the aglycone as an extraction artifact.

  20. Effects of elevated CO2 and ozone on phenolic glycosides of trembling aspen

    Science.gov (United States)

    James K. Nitao; Muraleedharan G. Nair; William J. Mattson; Daniel A. Herms; Bruce A. Birr; Mark D. Coleman; Terry M. Trier; J. G. Isebrands

    1996-01-01

    We tested the effects of elevated CO2 and ozone on concentrations of the phenolic glycosides salicortin and tremulacin in immature and mature foliage of the trembling aspen (Populus tremuloides) clones 216, 259, and 271.

  1. Synthesis of Two Tetrasaccharide Pentenyl Glycosides Related to the Pectic Rhamnogalacturonan I Polysaccharide

    DEFF Research Database (Denmark)

    Zakharova, Alexandra N.; Awan, Shahid I.; Nami, Faranak

    2018-01-01

    The synthesis of two protected tetrasaccharide pentenyl glycosides with diarabinan and digalactan branching related to the pectic polysaccharide rhamnogalacturonan I is reported. The strategy relies on the coupling of N-phenyl trifluoroacetimidate disaccharide donors to a common rhamnosyl acceptor...

  2. Cyclic Steroid Glycosides from the Starfish Echinaster luzonicus: Structures and Immunomodulatory Activities.

    Science.gov (United States)

    Kicha, Alla A; Kalinovsky, Anatoly I; Malyarenko, Timofey V; Ivanchina, Natalia V; Dmitrenok, Pavel S; Menchinskaya, Ekaterina S; Yurchenko, Ekaterina A; Pislyagin, Evgeny A; Aminin, Dmitry L; Huong, Trinh T T; Long, Pham Quoc; Stonik, Valentin A

    2015-06-26

    Five new steroid glycosides, luzonicosides B-E (2-5), belonging to a rare structure group of marine glycosides, containing carbohydrate moieties incorporated into a macrocycle, and a related open carbohydrate chain steroid glycoside, luzonicoside F (6), were isolated from the starfish Echinaster luzonicus along with the previously known cyclic steroid glycoside luzonicoside A (1). The structures of compounds 2-6 were established by extensive NMR and ESIMS techniques as well as chemical transformations. Luzonicoside A (1) at concentrations of 0.01-0.1 μM was shown to be potent in lysosomal activity stimulation, intracellular ROS level elevation, and NO synthesis up-regulation in RAW 264.7 murine macrophages. Luzonicoside D (4) was less active in these biotests.

  3. A new lignan glycoside from the stems of Zanthoxylum armatum DC.

    Science.gov (United States)

    Guo, Tao; Tang, Xiao-Feng; Chang, Jun; Wang, Ya

    2017-01-01

    A new lignan glycoside, (7S,8R)-guaiacylglycerol-ferulic acid ether-7-O-β-D-glucopyranoside (1), along with five known phenylpropanoids (2-6) and seven phenylpropanoid glycosides (7-13), were isolated from the stems of Zanthoxylum armatum DC. Their structures were elucidated by spectroscopic analysis. Compounds 2-8 and 11-13 were first isolated from Rutaceae and the others were isolated for the first time from Z. armatum.

  4. A new taraxastane-type triterpenoid glycoside from the roots of Clematis uncinata.

    Science.gov (United States)

    Li, Shuo-Guo; Li, Man-Mei; Zhao, Bing-Xin; Wang, Ying; Ye, Wen-Cai

    2015-01-01

    A new taraxastane-type triterpenoid glycoside, clematiunicinoside I (1), together with four known ones (2-5), was isolated from the roots of Clematis uncinata. The structure of the new compound was elucidated on the basis of spectroscopic analyses and acid hydrolysis. The cytotoxic activities of all the compounds against caski cervical cancer (Caski) cells were evaluated. This is the first report of the presence of taraxastane-type triterpenoid glycoside in the genus Clematis.

  5. Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics

    OpenAIRE

    Zhenzhen Xue; Bin Yang

    2016-01-01

    Phenylethanoid glycosides (PhGs) are widely distributed in traditional Chinese medicines as well as in other medicinal plants, and they were characterized by a phenethyl alcohol (C6-C2) moiety attached to a β-glucopyranose/β-allopyranose via a glycosidic bond. The outstanding activity of PhGs in diverse diseases proves their importance in medicinal chemistry research. This review summarizes new findings on PhGs over the past 10 years, concerning the new structures, their bioactivities, includ...

  6. Flavone glycosides from commercially available Lophatheri Herba and their chromatographic fingerprinting and quantitation

    OpenAIRE

    Fan, Jyun-Siang; Lee, I-Jung; Lin, Yun-Lian

    2015-01-01

    Lophatheri Herba (Danzhuye; LH), the dried leaves of Lophatherum gracile Brongn (Poaceae), is commonly used in Chinese herbal medicine as an antipyretic, antibacterial, and diuretic. Chemical analysis has been conducted to isolate and identify seven major flavonoid glycosides, including a new flavone C-glycoside, luteolin 6-C-β-D-glucuronopyranosyl-(1→2)-β-D-glucopyranoside (1), isoorientin (2), swertiajaponin (3), luteolin 6-C-β-D-glucuronopyranosyl-(1→2)-α-L-arabinopyranoside (4), isovitexi...

  7. Engineered yeast whole-cell biocatalyst for direct degradation of alginate from macroalgae and production of non-commercialized useful monosaccharide from alginate.

    Science.gov (United States)

    Takagi, Toshiyuki; Yokoi, Takahiro; Shibata, Toshiyuki; Morisaka, Hironobu; Kuroda, Kouichi; Ueda, Mitsuyoshi

    2016-02-01

    Alginate is a major component of brown macroalgae. In macroalgae, an endolytic alginate lyase first degrades alginate into oligosaccharides. These oligosaccharides are further broken down into monosaccharides by an exolytic alginate lyase. In this study, genes encoding various alginate lyases derived from alginate-assimilating marine bacterium Saccharophagus degradans were isolated, and their enzymes were displayed using the yeast cell surface display system. Alg7A-, Alg7D-, and Alg18J-displaying yeasts showed endolytic alginate lyase activity. On the other hand, Alg7K-displaying yeast showed exolytic alginate lyase activity. Alg7A, Alg7D, Alg7K, and Alg18J, when displayed on yeast cell surface, demonstrated both polyguluronate lyase and polymannuronate lyase activities. Additionally, polyguluronic acid could be much easily degraded by Alg7A, Alg7K, and Alg7D than polymannuronic acid. In contrast, polymannuronic acid could be much easily degraded by Alg18J than polyguluronic acid. We further constructed yeasts co-displaying endolytic and exolytic alginate lyases. Degradation efficiency by the co-displaying yeasts were significantly higher than single alginate lyase-displaying yeasts. Alg7A/Alg7K co-displaying yeast had maximum alginate degrading activity, with production of 1.98 g/L of reducing sugars in a 60-min reaction. This system developed, along with our findings, will contribute to the efficient utilization and production of useful and non-commercialized monosaccharides from alginate by Saccharomyces cerevisiae.

  8. Extraction, radiolabeling and in vivo biological evaluation of {sup 131}I labeled egonol glycosides extract

    Energy Technology Data Exchange (ETDEWEB)

    Akguel, Yurdanur; Pazar, Erdinc [Ege Univ., Izmir (Turkey). Chemistry Dept.; Yilmaz, Habibe; Sanlier, Senay Hamarat [Ege Univ., Izmir (Turkey). Biochemistry Dept.; Lambrecht, Fatma Yurt [Ege Univ., Izmir (Turkey). Dept. of Nuclear Applications; Yilmaz, Osman [Dokuz Eyluel Univ., Izmir (Turkey). Dept. of Lab. Animal Science

    2015-09-01

    Crude extract of S. officinalis L. was found to have suspending agent, hemolytic, antitumor, antioxidant and antimicrobial activities. Its major components benzofurans and benzofuran glycosides have antifungal, anticancer, antibacterial and anticomplement activities and display acetylcholinesterase-cyclooxygenase inhibitory and cytotoxic properties. Recently, it has been reported that egonolgentiobioside is a valuable target for structural modification and warrants further investigation for its potential as a novel pharmaceutical tool for the prevention of estrogen deficiency induced diseases. The aim of the current study is to perform in vivo biological evaluation of a glycosides extract, which was isolated from the fruits endocarp of Styrax officinalis L, identified as egonolgentiobioside and homoegonolgentiobioside and labeled with {sup 131}I. The radiolabeled glycosides extract was labeled with {sup 131}I with high yield. The labeled obtained radiolabeled compound was found to be quite stable and lipophilic. In order to determine its tissue distribution, an in vivo study was performed using healthy female Albino Wistar rats injected by {sup 131}I-glycosides. The biodistribution results showed that clearance of the radiolabeled compound is through the hepatobiliary pathway. The experimental study indicated that the radiolabeled glycosides extract accumulated in the large intestine. Therefore, the potential of {sup 131}I-glycosides might be evaluated in colon cancer cell lines and this might be a promising of tumor-imaging agent.

  9. Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur.

    Science.gov (United States)

    Senica, Mateja; Stampar, Franci; Veberic, Robert; Mikulic-Petkovsek, Maja

    2016-07-15

    Popular liqueurs made from apricot/cherry pits were evaluated in terms of their phenolic composition and occurrence of cyanogenic glycosides (CGG). Analyses consisted of detailed phenolic and cyanogenic profiles of cherry and apricot seeds as well as beverages prepared from crushed kernels. Phenolic groups and cyanogenic glycosides were analyzed with the aid of high-performance liquid chromatography (HPLC) and mass spectrophotometry (MS). Lower levels of cyanogenic glycosides and phenolics have been quantified in liqueurs compared to fruit kernels. During fruit pits steeping in the alcohol, the phenolics/cyanogenic glycosides ratio increased and at the end of beverage manufacturing process higher levels of total analyzed phenolics were detected compared to cyanogenic glycosides (apricot liqueur: 38.79 μg CGG per ml and 50.57 μg phenolics per ml; cherry liqueur 16.08 μg CGG per ml and 27.73 μg phenolics per ml). Although higher levels of phenolics are characteristic for liqueurs made from apricot and cherry pits these beverages nevertheless contain considerable amounts of cyanogenic glycosides. Copyright © 2016 Elsevier Ltd. All rights reserved.

  10. The contribution of wine-derived monoterpene glycosides to retronasal odour during tasting.

    Science.gov (United States)

    Parker, Mango; Black, Cory A; Barker, Alice; Pearson, Wes; Hayasaka, Yoji; Francis, I Leigh

    2017-10-01

    This study investigated the sensory significance of monoterpene glycosides during tasting, by retronasal perception of odorant aglycones released in-mouth. Monoterpene glycosides were isolated from Gewürztraminer and Riesling juices and wines, chemically characterised and studied using sensory time-intensity methodology, together with a synthesised monoterpene glucoside. When assessed in model wine at five times wine-like concentration, Gewürztraminer glycosides and geranyl glucoside gave significant fruity flavour, although at wine-like concentrations, or in the presence of wine volatiles, the effect was not significant. Gewürztraminer glycosides, geranyl glucoside and guaiacyl glucoside were investigated using a sensory panel (n=39), revealing large inter-individual variability, with 77% of panellists responding to at least one glycoside. The study showed for the first time that grape-derived glycosides can contribute perceptible fruity flavour, providing a means of enhancing flavour in wines, and confirms the results of previous studies that the effect is highly variable across individuals. Copyright © 2017 Elsevier Ltd. All rights reserved.

  11. Two New Flavonol Glycosides from Sarcopyramis bodinieri var. delicate

    Directory of Open Access Journals (Sweden)

    Yan Qiu

    2008-06-01

    Full Text Available Detailed chemical investigation of the herb Sarcopyramis bodinieri var. delicate resulted in the isolation of two new flavonol glycosides, namely, isorhamnetin-3-O-(6′′-OE- feruloyl-β-D-glucopyranoside (1 and isorhamnetin-3-O-(6′′-O-E-feruloyl-β-Dgalactopyranoside (2. In addition, four known compounds, quercetin-3-O-(6′′-acetyl-β-Dglucopyranoside (3, isorhamnetin-3-O-(6′′-acetyl-β-D-glucopyranoside (4, quercetin-3- O-(6′′-O-E-p-coumaroyl-β-D-glucopyranoside (5, and isorhamnetin-3-O-(6′′-O-E-pcoumaroyl- β-D-glucopyranoside (6 were obtained. The structures of the new isolates were determined by extensive spectroscopic analysis.

  12. Cytotoxicity of cardenolides and cardenolide glycosides from Asclepias curassavica.

    Science.gov (United States)

    Li, Jun-Zhu; Qing, Chen; Chen, Chang-Xiang; Hao, Xiao-Jiang; Liu, Hai-Yang

    2009-04-01

    A new cardenolide, 12beta,14beta-dihydroxy-3beta,19-epoxy-3alpha-methoxy-5alpha-card-20(22)-enolide (6), and a new doubly linked cardenolide glycoside, 12beta-hydroxycalotropin (13), together with eleven known compounds, coroglaucigenin (1), 12beta-hydroxycoroglaucigenin (2), calotropagenin (3), desglucouzarin (4), 6'-O-feruloyl-desglucouzarin (5), calotropin (7), uscharidin (8), asclepin (9), 16alpha-hydroxyasclepin (10), 16alpha-acetoxycalotropin (11), and 16alpha-acetoxyasclepin (12), were isolated from the aerial part of ornamental milkweed, Asclepias curassavica and chemically elucidated through spectral analyses. All the isolates were evaluated for their cytotoxic activity against HepG2 and Raji cell lines. The results showed that asclepin (9) had the strongest cytotoxic activity with an IC(50) value of 0.02 microM against the two cancer cell lines and the new compound 13 had significant cytotoxic activity with IC(50) values of 0.69 and 1.46 microM, respectively.

  13. Six new C21 steroidal glycosides from Asclepias curassavica L.

    Science.gov (United States)

    Li, Jun-Zhu; Liu, Hai-Yang; Lin, Yi-Ju; Hao, Xiao-Jiang; Ni, Wei; Chen, Chang-Xiang

    2008-07-01

    Six new C(21) steroidal glycosides, named curassavosides A-F (3-8), were obtained from the aerial parts of Asclepias curassavica (Asclepiadaceae), along with two known oxypregnanes, 12-O-benzoyldeacylmetaplexigenin (1) and 12-O-benzoylsarcostin (2). By spectroscopic methods, the structures of the six new compounds were determined as 12-O-benzoyldeacylmetaplexigenin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (3), 12-O-benzoylsarcostin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (4), sarcostin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (5), sarcostin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-D-digitoxopyranoside (6), 12-O-benzoyldeacylmetaplexigenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-canaropyranosyl-(1-->4)-beta-d-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (7), and 12-O-benzoylsarcostin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-d-canaropyranosyl-(1-->4)-beta-D-oleandropyranosyl-(1-->4)-beta-D-digitoxopyranoside (8), respectively. All compounds (1-8) were tested for in vitro cytotoxicity; only compound 3 showed weak inhibitory activity against Raji and AGZY cell lines.

  14. Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum.

    Science.gov (United States)

    Timité, Gaoussou; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Mirjolet, Jean-François; Duchamp, Olivier; Lacaille-Dubois, Marie-Aleth

    2013-04-01

    A phytochemical analysis of the whole plant of Allium schoenoprasum, has led to the isolation of four spirostane-type glycosides (1-4), and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25S)-spirost-5-en-3β,12β,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (1), (20S,25S)-spirost-5-en-3β,11α,21-triol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (2), laxogenin 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (3), and (25R)-5α-spirostan-3β,11α-diol 3-O-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside (4). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines. Copyright © 2012 Elsevier Ltd. All rights reserved.

  15. Hydroxycinnamoylmalated flavone C-glycosides from Lemna japonica.

    Science.gov (United States)

    Bai, Huan-Huan; Wang, Ni-Ni; Mi, Jiao; Yang, Tao; Fang, Dong-Mei; Wu, Lin-Wei; Zhao, Hai; Li, Guo-You

    2018-01-01

    Three previously undescribed flavone C-glycosides (1-3), along with seven known ones (4-10), were isolated and characterized from the smallest flowering aquatic plant, Lemna japonica. On the basis of spectroscopic analysis and alkaline hydrolysis, compounds 1-3 were identified to be luteolin 6-C-(2″-O-trans-caffeoyl-d-malate)-β-glucoside (1), apigenin 6-C-(2″-O-trans-caffeoyl-d-malate)-β-glucoside (2), and luteolin 6-C-(2″-O-trans-coumaroyl-d-malate)-β-glucoside (3). Compounds 1-3 are characteristic of a trans-coumaroyl-d-malate or trans-caffeoyl-d-malate linked to C-2″ of the glucose, which was reported for the first time. Compounds 1-3 exhibited weak cytotoxicity against HepG-2, SW-620, and A-549 cell lines, with IC 50 values between 42.5 and 19.2μg/ml, and moderate antioxidant activity. Meanwhile compound 3 displayed moderate nematocidal activity with an EC 50 value of 1.56mg/ml. Copyright © 2017 Elsevier B.V. All rights reserved.

  16. Antitrypanosomal isothiocyanate and thiocarbamate glycosides from Moringa peregrina.

    Science.gov (United States)

    Ayyari, Mahdi; Salehi, Peyman; Ebrahimi, Samad Nejad; Zimmermann, Stefanie; Portmann, Lena; Krauth-Siegel, R Luise; Kaiser, Marcel; Brun, Reto; Rezadoost, Hassan; Rezazadeh, Shamsali; Hamburger, Matthias

    2014-01-01

    O-Methyl (1), O-ethyl (2), and O-butyl (3) 4-[(α-L-rhamnosyloxy) benzyl] thiocarbamate (E), along with 4-(α-L-rhamnosyloxy) benzyl isothiocyanate (4) have been isolated from the aerial parts of Moringa peregrina. The compounds were tested for in vitro activity against Trypanosoma brucei rhodesiense and cytotoxicity in rat skeletal myoblasts (L6 cells). The most potent compound was 4 with an IC50 of 0.10 µM against T.b. rhodesiense and a selectivity index of 73, while the thiocarbamate glycosides 1, 2, and 3 showed only moderate activity. Intraperitoneal administration of 50 mg/kg body weight/day of 4 in the T.b. rhodesiense STIB 900 acute mouse model revealed significant in vivo toxicity. Administration of 10 mg/kg body weight/day resulted in a 95% reduction of parasitemia on day 7 postinfection, but did not cure the animals. Because of its high in vitro activity and its ability to irreversibly inhibit trypanothione reductase, an attractive parasite-specific target enzyme, 4-[(α-L-rhamnosyloxy) benzyl] isothiocyanate (4), can be considered as a lead structure for the development and characterization of novel antitrypanosomal drugs. Georg Thieme Verlag KG Stuttgart · New York.

  17. Trypanocidal withanolides and withanolide glycosides from Dunalia brachyacantha.

    Science.gov (United States)

    Bravo B, J A; Sauvain, M; Gimenez T, A; Balanza, E; Serani, L; Laprévote, O; Massiot, G; Lavaud, C

    2001-06-01

    Two new withanolide glycosides, (20R,22R)-O-(3)-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide (3) and (20R,22R)-O-(3)-beta-D-xylopyranosyl(1-->3)-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranosyl-1 alpha-acetoxy-12 beta,20-dihydroxywitha-5,24-dienolide (4), were isolated from the leaves and root of Dunalia brachyacantha. Their aglycones, (20R,22R)-1 alpha,12 beta-diacetoxy-3 beta,20-dihydroxywitha-5,24-dienolide (or 1 alpha,12 beta-diacetyldunawithagenine) and (20R,22R)-1 alpha-acetoxy-3 beta,12 beta,20-trihydroxywitha-5,24-dienolide (or 1 alpha-acetyl-12 beta-hydroxydunawithagenine), are novel. The known 18-acetoxywithanolide D (1) and 18-acetoxy-5,6-deoxy-5-withenolide D (2) were also isolated from the leaves. These last two compounds were shown to be responsible for the trypanocidal, leishmanicidal, and bactericidal activities manifested by the crude ethanolic extract. The structures were deduced from spectroscopic data and on the basis of chemical evidence.

  18. Antimicrobial and cytotoxic phenolics and phenolic glycosides from Sargentodoxa cuneata.

    Science.gov (United States)

    Zeng, Xiaobin; Wang, Hai; Gong, Zhongqing; Huang, Jinghui; Pei, Weijing; Wang, Xueyan; Zhang, Jingzhao; Tang, Xudong

    2015-03-01

    Five new phenolic glycosides, Sargentodosides A-E, and two new dihydronaphthalene lignans, Sargentodognans F-G, together with thirty-two known phenolic compounds were isolated from the 60% ethanol extracts of Sargentodoxa cuneata. Their structures including absolute configurations were determined by spectroscopic analysis and electronic circular dichroism experiments. In bioscreening experiments, twelve compounds (22-26, 29, 33-34, 36, 38) exhibited antibacterial activities against S. aureus ATCC 29213 with minimum inhibitory concentration (MIC) values of 2-516μg/mL. And compound 29 showed the highest antibacterial activity against S. aureus ATCC 29213 with MIC values of 2μg/mL, while the MIC values of levofloxacin was 8μg/mL. Three compounds (29, 33, 36) exhibited antibacterial activities against S. aureus ATCC 25923 with MIC values of 256-516μg/mL. Two compounds (29, 33) exhibited antibacterial activities against A. baumanii ATCC 19606 with MIC values of 128-516μg/mL. However, no compound exhibited antimicrobial activities against C. albicans ATCC 10231. Moreover, three compounds (10, 25, 36) exhibited significant inhibition of proliferation in the two cell lines Hela and Siha, and showed stronger inhibitive activity of these two selected cell lines than cisplatin in the cytotoxic assay. Thus, S. cuneata is a potential plant source for further research targeting bacteria and cancer diseases. Copyright © 2015 Elsevier B.V. All rights reserved.

  19. Additional Minor Diterpene Glycosides from Stevia rebaudiana Bertoni

    Directory of Open Access Journals (Sweden)

    Indra Prakash

    2013-10-01

    Full Text Available Two additional novel minor diterpene glycosides were isolated from the commercial extract of the leaves of Stevia rebaudiana Bertoni. The structures of the new compounds were identified as 13-{β-D-glucopyranosyl-(1→2-O-[β-D-glucopyranosyl-(1→3-β-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {β-D-xylopyranosyl-(1→2-O-[β-D-glucopyranosyl-(1→3]-O-β-D-glucupyranosyl-ester} (1, and 13-{β-D-6-deoxy-glucopyranosyl-(1→2-O-[β-D-glucopyranosyl-(1→3-β-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {β-D-glucopyranosyl-(1→2-O-[β-D-glucopyranosyl-(1→3-β-D-gluco-pyranosyl-ester} (2, on the basis of extensive 1D (1H- and 13C- 2D NMR (COSY, HSQC and HMBC and MS spectroscopic data as well as chemical studies.

  20. Flavonoid Glycosides of Polygonum capitatum Protect against Inflammation Associated with Helicobacter pylori Infection.

    Directory of Open Access Journals (Sweden)

    Shu Zhang

    Full Text Available The antibacterial and anti-inflammatory activities, and protective effects of extracts (flavonoid glycosides of Polygonum capitatum were investigated to detect the evidence for the utilization of the herb in the clinical therapy of gastritis caused by H. pylori. A mouse gastritis model was established using H. pylori. According to treating methods, model mice were random assigned into a model group (MG group, a triple antibiotics group (TG group, clarithromycin, omeprazole and amoxicillin, low/middle/high concentrations of flavonoid glycosides groups (LF, MF and HF groups and low/middle/high concentrations of flavonoid glycosides and amoxicillin groups (LFA, MFA and HFA groups. A group with pathogen-free mice was regarded as a control group (CG group. The eradicate rates of H. pylori were 100%, 93%, 89% in TG, MFA and HF groups. The serum levels of IFN-gamma and gastrin were higher in a MG group than those from all other groups (P < 0.05. The serum levels of IFN-gamma and gastrin were reduced significantly in LF, MF and HF groups (P < 0.05 while little changes were observed in LFA, MFA and HFA groups. In contrast, the serum levels of IL-4 were lower and higher in MG and CG groups compared with other groups (P<0.05. The serum levels of IL-4 were increased significantly in LF, MF and HF groups (P < 0.05 while little changes were found in LFA, MFA and HFA groups. According to pathological scores, flavonoid glycosides therapy showed better protection for gastric injuries than the combination of flavonoid glycoside and amoxicillin (P < 0.05. The results suggested that flavonoid glycoside has repairing functions for gastric injuries. The results suggest that the plant can treat gastritis and protect against gastric injuries. The flavonoid glycosides from Polygonum capitatum should be developed as a potential drug for the therapy of gastritis caused by H. pylori.

  1. Cardiac Glycoside Glucoevatromonoside Induces Cancer Type-Specific Cell Death

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    Naira F. Z. Schneider

    2018-03-01

    Full Text Available Cardiac glycosides (CGs are natural compounds used traditionally to treat congestive heart diseases. Recent investigations repositioned CGs as potential anticancer agents. To discover novel cytotoxic CG scaffolds, we selected the cardenolide glucoevatromonoside (GEV out of 46 CGs for its low nanomolar anti-lung cancer activity. GEV presented reduced toxicity toward non-cancerous cell types (lung MRC-5 and PBMC and high-affinity binding to the Na+/K+-ATPase α subunit, assessed by computational docking. GEV-induced cell death was caspase-independent, as investigated by a multiparametric approach, and culminates in severe morphological alterations in A549 cells, monitored by transmission electron microscopy, live cell imaging and flow cytometry. This non-canonical cell death was not preceded or accompanied by exacerbation of autophagy. In the presence of GEV, markers of autophagic flux (e.g. LC3I-II conversion were impacted, even in presence of bafilomycin A1. Cell death induction remained unaffected by calpain, cathepsin, parthanatos, or necroptosis inhibitors. Interestingly, GEV triggered caspase-dependent apoptosis in U937 acute myeloid leukemia cells, witnessing cancer-type specific cell death induction. Differential cell cycle modulation by this CG led to a G2/M arrest, cyclin B1 and p53 downregulation in A549, but not in U937 cells. We further extended the anti-cancer potential of GEV to 3D cell culture using clonogenic and spheroid formation assays and validated our findings in vivo by zebrafish xenografts. Altogether, GEV shows an interesting anticancer profile with the ability to exert cytotoxic effects via induction of different cell death modalities.

  2. Bioprospecting metagenomics of decaying wood: mining for new glycoside hydrolases

    Energy Technology Data Exchange (ETDEWEB)

    Li L. L.; van der Lelie D.; Taghavi, S.; McCorkle, S. M.; Zhang, Y.-B.; Blewitt, M. G.; Brunecky, R.; Adney, W. S.; Himmel, M. E.; Brumm, P.; Drinkwater, C.; Mead, D. A.; Tringe, S. G.

    2011-08-01

    To efficiently deconstruct recalcitrant plant biomass to fermentable sugars in industrial processes, biocatalysts of higher performance and lower cost are required. The genetic diversity found in the metagenomes of natural microbial biomass decay communities may harbor such enzymes. Our goal was to discover and characterize new glycoside hydrolases (GHases) from microbial biomass decay communities, especially those from unknown or never previously cultivated microorganisms. From the metagenome sequences of an anaerobic microbial community actively decaying poplar biomass, we identified approximately 4,000 GHase homologs. Based on homology to GHase families/activities of interest and the quality of the sequences, candidates were selected for full-length cloning and subsequent expression. As an alternative strategy, a metagenome expression library was constructed and screened for GHase activities. These combined efforts resulted in the cloning of four novel GHases that could be successfully expressed in Escherichia coli. Further characterization showed that two enzymes showed significant activity on p-nitrophenyl-{alpha}-L-arabinofuranoside, one enzyme had significant activity against p-nitrophenyl-{beta}-D-glucopyranoside, and one enzyme showed significant activity against p-nitrophenyl-{beta}-D-xylopyranoside. Enzymes were also tested in the presence of ionic liquids. Metagenomics provides a good resource for mining novel biomass degrading enzymes and for screening of cellulolytic enzyme activities. The four GHases that were cloned may have potential application for deconstruction of biomass pretreated with ionic liquids, as they remain active in the presence of up to 20% ionic liquid (except for 1-ethyl-3-methylimidazolium diethyl phosphate). Alternatively, ionic liquids might be used to immobilize or stabilize these enzymes for minimal solvent processing of biomass.

  3. Bioprospecting metagenomics of decaying wood: mining for new glycoside hydrolases

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    Li Luen-Luen

    2011-08-01

    Full Text Available Abstract Background To efficiently deconstruct recalcitrant plant biomass to fermentable sugars in industrial processes, biocatalysts of higher performance and lower cost are required. The genetic diversity found in the metagenomes of natural microbial biomass decay communities may harbor such enzymes. Our goal was to discover and characterize new glycoside hydrolases (GHases from microbial biomass decay communities, especially those from unknown or never previously cultivated microorganisms. Results From the metagenome sequences of an anaerobic microbial community actively decaying poplar biomass, we identified approximately 4,000 GHase homologs. Based on homology to GHase families/activities of interest and the quality of the sequences, candidates were selected for full-length cloning and subsequent expression. As an alternative strategy, a metagenome expression library was constructed and screened for GHase activities. These combined efforts resulted in the cloning of four novel GHases that could be successfully expressed in Escherichia coli. Further characterization showed that two enzymes showed significant activity on p-nitrophenyl-α-L-arabinofuranoside, one enzyme had significant activity against p-nitrophenyl-β-D-glucopyranoside, and one enzyme showed significant activity against p-nitrophenyl-β-D-xylopyranoside. Enzymes were also tested in the presence of ionic liquids. Conclusions Metagenomics provides a good resource for mining novel biomass degrading enzymes and for screening of cellulolytic enzyme activities. The four GHases that were cloned may have potential application for deconstruction of biomass pretreated with ionic liquids, as they remain active in the presence of up to 20% ionic liquid (except for 1-ethyl-3-methylimidazolium diethyl phosphate. Alternatively, ionic liquids might be used to immobilize or stabilize these enzymes for minimal solvent processing of biomass.

  4. Low temperature lignocellulose pretreatment: effects and interactions of pretreatment pH are critical for maximizing enzymatic monosaccharide yields from wheat straw

    DEFF Research Database (Denmark)

    Pedersen, Mads; Johansen, Katja S.; Meyer, Anne S.

    2011-01-01

    Background: The recent development of improved enzymes and pentose-using yeast for cellulosic ethanol processes calls for new attention to the lignocellulose pretreatment step. This study assessed the influence of pretreatment pH, temperature, and time, and their interactions on the enzymatic...... C for 10 min. The maximal enzymatic glucose and xylose yields from the solid, pretreated wheat straw fraction were obtained after pretreatments at the most extreme pH values (pH 1 or pH 13) at the maximum pretreatment temperature of 140 degrees C. Surface response models revealed significantly...... correlating interactions of the pretreatment pH and temperature on the enzymatic liberation of both glucose and xylose from pretreated, solid wheat straw. The influence of temperature was most pronounced with the acidic pretreatments, but the highest enzymatic monosaccharide yields were obtained after...

  5. Monoterpenyl Glycosyltransferases Differentially Contribute to Production of Monoterpenyl Glycosides in Two Aromatic Vitis vinifera Varieties.

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    Li, Xiang-Yi; Wen, Ya-Qin; Meng, Nan; Qian, Xu; Pan, Qiu-Hong

    2017-01-01

    HIGHLIGHTS A similar trend on accumulation of glycosidically bound monoterpenes was observed in both varietiesTwo VvGT7 alleles mutations occurred at key sites in Muscat blanc à PetitVvGT14 exerted a major role in production of monoterpenyl glycosides in both varieties Terpenoids are the major aroma components and generally exist as both free and glycosidically-bound forms, of which nonvolatile glycosides account for a large fraction in grape berries. Our previous study has indicated that differential accumulation of monoterpenyl glycosides in Vitis vinifera "Muscat blanc à Petit" between two regions is closely correlated to monoterpenyl glucosyltransferase (VvGT14, XM_002285734.2) transcript abundance. However, it has not been determined yet whether this correlation also exists in other Vitis vinifera varieties. This study investigated the evolution of free and glycosidically bound monoterpenes in two Vitis vinifera variety "Muscat blanc à Petit" and "Gewurztraminer" under two vintages, and further assessed the relation between the accumulation of bound monoterpenes and two monoterpenyl glycosyltransferase transcript levels. Results showed that free monoterpenes exhibited three evolution patterns in both varieties during berry development of two vintages, whereas glycosidically bound monoterpenes showed a concentration elevation with berry maturation. The Cis-rose oxide and geraniol were major components contributing to the aroma odors of "Gewürztraminer" grapes while linalool was major aroma contributor to the "Muscat blanc à Petit grain" grapes. The accumulation of glycosidically bound monoterpenes in both varieties was accompanied with the high expression of VvGT7 (XM_002276510.2) and VvGT14. Only one allele of VvGT7 was found in the variety "Gewürztraminer" and no mutation was observed in its enzyme active sites. XB-VvGT7-4 and XB-VvGT7-5 were two alleles of VvGT7 detected in "Muscat blanc à Petit grain." The mutation on its enzyme active site inhibited

  6. Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed–disarmed strategy

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    Abhijeet K. Kayastha

    2013-10-01

    Full Text Available The synthesis of oligosaccharides is still a challenging task as there is no universal glycosyl donor for the synthesis of all oligosaccharides. The gold catalysis for glycosidation reactions, in which alkynylated glycosides are used, has emerged as one of the versatile options in this regard. A cleavage of the interglycosidic bond that was thought to be due to the higher reaction temperature and the acidic medium was observed during the synthesis of trisaccharides. In addition, a very little percentage of deprotection of benzyl protecting groups at the C-6 position was observed and no deprotection of benzyl ethers in aliphatic molecules was noticed. In order to overcome this fact, a collection of leaving groups that contain an alkynyl moiety were screened. It was found that 1-ethynylcyclohexanyl (Ech glycosides are suitable for carrying out the glycosidation at 25 °C in the presence of 5 mol % each of AuCl3 and AgSbF6. Subsequently, Ech-glycosides were observed to be suitable for the synthesis of trisaccharides under gold catalysis conditions.

  7. Variation of quercetin glycoside derivatives in three onion (Allium cepa L.) varieties.

    Science.gov (United States)

    Kwak, Jung-Ho; Seo, Jeong Min; Kim, Na-Hyung; Arasu, Mariadhas Valan; Kim, Sunggil; Yoon, Moo Kyoung; Kim, Sun-Ju

    2017-09-01

    The aim of this study was to quantify the contents of individual quercetin glycosides in red, yellow and chartreuse onion by High Performance Liquid Chromatography (HPLC) analysis. Acid hydrolysis of individual quercetin glycosides using 6 M hydrochloric acid guided to identify and separate quercetin 7,4'-diglucoside, quercetin 3-glucoside, quercetin 4'-glucoside, and quercetin. The contents of total quercetin glycosides varied extensively among three varieties (ranged from 16.10 to 103.93 mg/g DW). Quercetin was the predominant compound that accounted mean 32.21 mg/g DW in red onion (43.6% of the total) and 127.92 mg/g DW in chartreuse onion (78.3% of the total) followed by quercetin 3-glucoside (28.83 and 24.16 mg/g DW) respectively. Quercetin 3-glucoside levels were much higher in yellow onion (43.85 mg/g DW) followed by quercetin 30.08 mg/g DW. Quercetin 4'-glucoside documented the lowest amount that documented mean 2.4% of the total glycosides. The varied contents of glycosides present in the different onion varieties were significant.

  8. A Novel Diterpene Glycoside with Nine Glucose Units from Stevia rebaudiana Bertoni.

    Science.gov (United States)

    Prakash, Indra; Ma, Gil; Bunders, Cynthia; Charan, Romila D; Ramirez, Catherine; Devkota, Krishna P; Snyder, Tara M

    2017-01-31

    Following our interest in new diterpene glycosides with better taste profiles than that of Rebaudioside M, we have recently isolated and characterized Rebaudioside IX-a novel steviol glycoside-from a commercially-supplied extract of Stevia rebaudiana Bertoni. This molecule contains a hexasaccharide group attached at C-13 of the central diterpene core, and contains three additional glucose units when compared with Rebaudioside M. Here we report the complete structure elucidation-based on extensive Nuclear Magnetic Resonance (NMR) analysis (1H, 13C, Correlation Spectroscopy (COSY), Heteronuclear Single Quantum Coherence-Distortionless Enhancement Polarization Transfer (HSQC-DEPT), Heteronuclear Multiple Bond Correlation (HMBC), 1D Total Correlation Spectroscopy (TOCSY), Nuclear Overhauser Effect Spectroscopy (NOESY)) and mass spectral data-of this novel diterpene glycoside with nine sugar moieties and containing a relatively rare 16 α-linked glycoside. A steviol glycoside bearing nine glucose units is unprecedented in the literature, and could have an impact on the natural sweetener catalog.

  9. Variation of quercetin glycoside derivatives in three onion (Allium cepa L. varieties

    Directory of Open Access Journals (Sweden)

    Jung-Ho Kwak

    2017-09-01

    Full Text Available The aim of this study was to quantify the contents of individual quercetin glycosides in red, yellow and chartreuse onion by High Performance Liquid Chromatography (HPLC analysis. Acid hydrolysis of individual quercetin glycosides using 6 M hydrochloric acid guided to identify and separate quercetin 7,4′-diglucoside, quercetin 3-glucoside, quercetin 4′-glucoside, and quercetin. The contents of total quercetin glycosides varied extensively among three varieties (ranged from 16.10 to 103.93 mg/g DW. Quercetin was the predominant compound that accounted mean 32.21 mg/g DW in red onion (43.6% of the total and 127.92 mg/g DW in chartreuse onion (78.3% of the total followed by quercetin 3-glucoside (28.83 and 24.16 mg/g DW respectively. Quercetin 3-glucoside levels were much higher in yellow onion (43.85 mg/g DW followed by quercetin 30.08 mg/g DW. Quercetin 4′-glucoside documented the lowest amount that documented mean 2.4% of the total glycosides. The varied contents of glycosides present in the different onion varieties were significant.

  10. Hydrolysis and transformation of grape glycosidically bound volatile compounds during fermentation with three Saccharomyces yeast strains.

    Science.gov (United States)

    Ugliano, Maurizio; Bartowsky, Eveline J; McCarthy, Jane; Moio, Luigi; Henschke, Paul A

    2006-08-23

    The ability of three Saccharomyces wine yeasts (S. cerevisiae AWRI 838, S. cerevisiae AWRI 1537, and S. bayanus AWRI 1375) to liberate volatile compounds from sugar-bound aroma precursors was investigated using synthetic and grape glycosides under different experimental conditions. In model systems involving the incubation of yeast cells with either synthetic or grape-derived glycosides under conditions more favorable for glycosidase activities and less favorable for acid-catalyzed hydrolysis (pH 5.0 and 30 degrees C), all yeast strains studied proved to be capable of hydrolyzing glycosides, with S. bayanus AWRI 1375 displaying greater hydrolytic activity than S. cerevisiae AWRI 838 and AWRI 1537. During the fermentation of a chemically defined grape juice-like medium containing glycosidic precursors extracted from Vitis vinifera cv. White Frontignac (synonym Muscat à Petit Grains Blanc), all yeasts promoted a significant hydrolysis of different precursors, which varied according to the chemical structures of both the sugar and the aglycon moieties, as determined by GC-MS analysis of trifluoroacetylated derivatives. Hydrolysis of the White Frontignac derived glycosidic precursors during fermentation resulted in the release of monoterepene alcohols, terpene oxides, terpene diols, and 3-oxo-alpha-ionol, demonstrating the significant potential of these yeast strains to contribute to wine varietal volatile composition during alcoholic fermentation.

  11. Extraction of stevia glycosides with CO2 + water, CO2 + ethanol, and CO2 + water + ethanol

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    A. Pasquel

    2000-09-01

    Full Text Available Stevia leaves are an important source of natural sugar substitute. There are some restrictions on the use of stevia extract because of its distinctive aftertaste. Some authors attribute this to soluble material other than the stevia glycosides, even though it is well known that stevia glycosides have to some extent a bitter taste. Therefore, the purpose of this work was to develop a process to obtain stevia extract of a better quality. The proposed process includes two steps: i Pretreatment of the leaves by SCFE; ii Extraction of the stevia glycosides by SCFE using CO2 as solvent and water and/or ethanol as cosolvent. The mean total yield for SCFE pretreatment was 3.0%. The yields for SCFE with cosolvent of stevia glycosides were below 0.50%, except at 120 bar, 16°C, and 9.5% (molar of water. Under this condition, total yield was 3.4%. The quality of the glycosidic fraction with respect to its capacity as sweetener was better for the SCFE extract as compared to extract obtained by the conventional process. The overall extraction curves were well described by the Lack extended model.

  12. [Effect of triterpene glycosides on RNA biosynthesis in a yeast cell culture of Saccharomyces carlsbergensis].

    Science.gov (United States)

    Anisimov, M M; Baranova, S I; Strigina, L I; Chetyrina, N S; Sokol'skiĭ, I N

    1977-09-01

    The effect of triterpen glycosides of cauloside C from Caulophyllum robustum, theasaponine from Thea sinensis ahd stichoposide A from Stichopus japonicus on multiplication and biosynthesis of RNA in the cells of a 7-hour culture of Saccharomyces carlsbergensis was studied. It was shown that cauloside C, theasaponine and stichoposide A in concentrations of 7.5 gamma/ml inhibited multiplication of the yeast cells by 65, 10 and 90 per cent respectively. The summation RNA of the yeast cells is divided into 3 zones on Sephadex G-100. The glycosides induced no pronounced changes in the chromotographic profile of RNA. Biosynthesis of the transport and ribosomal RNA were inhibited to the same extent. Triterpen glycosides inhibited the biosynthesis of RNA at the stage of 14C-uridine in corporation into the nucleotide pool of the yeast cells.

  13. Flavonoid Glycosides of Polygonum capitatum Protect against Inflammation Associated with Helicobacter pylori Infection.

    Science.gov (United States)

    Zhang, Shu; Mo, Fei; Luo, Zhaoxun; Huang, Jian; Sun, Chaoqin; Zhang, Ran

    2015-01-01

    The antibacterial and anti-inflammatory activities, and protective effects of extracts (flavonoid glycosides) of Polygonum capitatum were investigated to detect the evidence for the utilization of the herb in the clinical therapy of gastritis caused by H. pylori. A mouse gastritis model was established using H. pylori. According to treating methods, model mice were random assigned into a model group (MG group), a triple antibiotics group (TG group, clarithromycin, omeprazole and amoxicillin), low/middle/high concentrations of flavonoid glycosides groups (LF, MF and HF groups) and low/middle/high concentrations of flavonoid glycosides and amoxicillin groups (LFA, MFA and HFA groups). A group with pathogen-free mice was regarded as a control group (CG group). The eradicate rates of H. pylori were 100%, 93%, 89% in TG, MFA and HF groups. The serum levels of IFN-gamma and gastrin were higher in a MG group than those from all other groups (P H. pylori.

  14. Total peroxynitrite scavenging capacity of phenylethanoid and flavonoid glycosides from the flowers of Buddleja officinalis.

    Science.gov (United States)

    Tai, Bui Huu; Jung, Bong Yong; Cuong, Nguyen Manh; Linh, Pham Thuy; Tung, Nguyen Huu; Nhiem, Nguyen Xuan; Huong, Tran Thu; Anh, Ngo Thi; Kim, Jeong Ah; Kim, Sang Kyum; Kim, Young Ho

    2009-12-01

    Nine compounds, including six phenylethanoid glycosides: acteoside (1); bioside (2); echinacoside (3); poliumoside (4); phenylethyl glycoside (5); salidroside (6) and three flavonoids; linarin (7); apigenin (8); isorhoifolin (9), were isolated from the flowers of Buddleja officinalis MAXIM. (Buddlejaceae). Chemical structures were confirmed by (1)H-, and (13)C-NMR, and MS spectral methods and compared with those reported in the literature. Antioxidant activities of the methanol and water extracts, and all isolated compounds were evaluated using the total oxidant scavenging capacity (TOSC) assay against peroxynitrite. Results of the assay showed that the phenylethanoid glycosides, a major class of compounds of the flowers of B. officinalis, possess strong antioxidant activity. Of these, acteoside, echinacoside and poliumoside have 9.9-, 9.8- and 9.5-fold TOSC value, respectively, compared with the positive control, Trolox.

  15. Quantitative determination of triterpenoid glycosides in Fatsia japonica Decne. & Planch. using high performance liquid chromatography.

    Science.gov (United States)

    Ye, Xuewei; Yu, Siran; Lian, Xiao-Yuan; Zhang, Zhizhen

    2014-01-01

    Fatsia japonica Decne. & Planch. is a triterpenoid glycoside-rich herb with anti-inflammatory activity for the treatment of rheumatoid arthritis. A method for quantitative analysis of the complex triterpenoid glycosides in this medicinal plant has not been established so far. In this study, a high performance liquid chromatography (HPLC) method was developed for simultaneous qualification of 11 glycosides in F. japonica. The analysis was performed on an ODS-2 Hypersil column (250mm×4.6mm, 5μm) with a binary gradient mobile phase of water and acetonitrile. The established HPLC method was validated in terms of linearity, sensitivity, stability, precision, accuracy, and recovery. Results showed that this method had good linearity with R(2) at 0.99992-0.99999 in the test range of 0.04-9.00μg/μL. The limit of detection (LOD) and limit of quantification (LOQ) for the standard compounds were 0.013-0.020μg/μL and 0.040-0.060μg/μL. The relative standard deviations (RSDs%) of run variations were 0.83-1.40% for intra-day and 0.84-3.59% for inter-day. The analyzed compounds in the samples were stable for at least 36h, and the spike recoveries of the detected glycosides were 99.67-103.11%. The developed HPLC method was successfully applied for the measurements of the contents of 11 triterpenoid glycoside in different parts of F. japonica. Taken together, the HPLC method newly developed in this study could be used for qualitative and quantitative analysis of the bioactive triterpenoid glycosides in F. japonica and its products. Copyright © 2013 Elsevier B.V. All rights reserved.

  16. STEROIDAL GLYCOSIDES FROM THE SEEDS OF HYOSCYAMUS NIGER L. AND THEIR ANTIFUNGAL ACTIVITY

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    Irina Lunga

    2007-06-01

    Full Text Available Phytochemical analysis of the seeds of Hyocyamus niger L. (Solonaceae resulted in the isolation of six steroidal glycosides, two furostanol (1, 2 and four spirostanol saponins (3, 4, 5, 6, which were found in this plant for the first time. The structures of these compounds were determined by detailed analysis of their spectral data, including two-dimensional NMR spectroscopy and MS spectroscopy. The antifungal activity of a crude steroidal glycoside extract, fractions of spirostanoles and individual glicosides was investigated in vitro against a panel of human pathogenic fungi, yeasts as well as dermatophytes and filamentous species.

  17. HOPEAPHENOL-O-GLYCOSIDE, A COMPOUND ISOLATED FROM STEM BARK Anisoptera marginata (Dipterocarpaceae

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    Sri Atun

    2010-06-01

    Full Text Available Isolation and structure elucidation of some compounds from stem bark of Anisoptera marginata had been done. The isolation of those compounds was carried out by chromatographyc method and structure elucidation was performed by interpretation of spectroscopic data, including UV, IR,  1H and 13C NMR 1D and 2D, and FABMS. From acetone extract stem bark A. marginata we isolated five known compounds namely bergenin (1, (--ε-vinipherin (2, (--ampelopsin A (3, vaticanol B (4, (--hopeaphenol (5, and a glycoside compound namely hopeaphenol-O- glycoside (6.   Keywords: Dipterocarpaceae; Anisoptera marginata; hopeaphenol-O-glucoside

  18. Dietary flavonoid aglycones and their glycosides: Which show better biological significance?

    Science.gov (United States)

    Xiao, Jianbo

    2017-06-13

    The dietary flavonoids, especially their glycosides, are the most vital phytochemicals in diets and are of great general interest due to their diverse bioactivity. The natural flavonoids almost all exist as their O-glycoside or C-glycoside forms in plants. In this review, we summarized the existing knowledge on the different biological benefits and pharmacokinetic behaviors between flavonoid aglycones and their glycosides. Due to various conclusions from different flavonoid types and health/disease conditions, it is very difficult to draw general or universally applicable comments regarding the impact of glycosylation on the biological benefits of flavonoids. It seems as though O-glycosylation generally reduces the bioactivity of these compounds - this has been observed for diverse properties including antioxidant activity, antidiabetes activity, anti-inflammation activity, antibacterial, antifungal activity, antitumor activity, anticoagulant activity, antiplatelet activity, antidegranulating activity, antitrypanosomal activity, influenza virus neuraminidase inhibition, aldehyde oxidase inhibition, immunomodulatory, and antitubercular activity. However, O-glycosylation can enhance certain types of biological benefits including anti-HIV activity, tyrosinase inhibition, antirotavirus activity, antistress activity, antiobesity activity, anticholinesterase potential, antiadipogenic activity, and antiallergic activity. However, there is a lack of data for most flavonoids, and their structures vary widely. There is also a profound lack of data on the impact of C-glycosylation on flavonoid biological benefits, although it has been demonstrated that in at least some cases C-glycosylation has positive effects on properties that may be useful in human healthcare such as antioxidant and antidiabetes activity. Furthermore, there is a lack of in vivo data that would make it possible to make broad generalizations concerning the influence of glycosylation on the benefits of

  19. Electrospray-ionization mass spectrometry of mixtures of triterpene glycosides with paracetamol

    Science.gov (United States)

    Lekar, A. V.; Vetrova, E. V.; Borisenko, N. I.; Yakovishin, L. A.; Grishkovets, V. I.

    2010-11-01

    Molecular complexation of paracetamol with hederagenin 3-O-α-L-rhamnopyranosyl-(1 → 2)-O-α-L-arabinopyranoside (α-hederin) and its 28-O-α-L-rhamnopyranosyl-(1 → 4)-O-β-D-glucopyranosyl-(1 → 6)-O-β-Dglucopyranosyl ether (hederasaponin C) was investigated for the first time using electrospray-ionization mass spectrometry (ESI-MS). The glycosides form complexes with paracetamol in a 1:1 molar ratio. The hederasaponin C complex is more stable. The structures of the glycosides and paracetamol are concluded to have an impact on the complexation process.

  20. Antiviral isoflavonoid sulfate and steroidal glycosides from the fruits of Solanum torvum.

    Science.gov (United States)

    Arthan, Damrongkiet; Svasti, Jisnuson; Kittakoop, Prasat; Pittayakhachonwut, Daraporn; Tanticharoen, Morakot; Thebtaranonth, Yodhathai

    2002-02-01

    The C-4 sulfated isoflavonoid, torvanol A (1), and the steroidal glycoside, torvoside H (3), together with the known glycoside, torvoside A (2), were isolated from a MeOH extract of Solanum torvum fruits. Upon enzymatic hydrolysis with beta-glucosidase, torvoside A (2) and torvoside H (3) yielded the corresponding acetal derivatives 4 and 5, respectively. Torvanol A (1), torvoside H (3) and compound 5 exhibited antiviral activity (herpes simplex virus type 1) with IC(50) values of 9.6, 23.2 and 17.4 microg/ml, respectively. Compounds 1-5 showed no cytotoxicity (at 50 microg/ml) against BC, KB and Vero cell lines.

  1. Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics.

    Science.gov (United States)

    Xue, Zhenzhen; Yang, Bin

    2016-07-29

    Phenylethanoid glycosides (PhGs) are widely distributed in traditional Chinese medicines as well as in other medicinal plants, and they were characterized by a phenethyl alcohol (C₆-C₂) moiety attached to a β-glucopyranose/β-allopyranose via a glycosidic bond. The outstanding activity of PhGs in diverse diseases proves their importance in medicinal chemistry research. This review summarizes new findings on PhGs over the past 10 years, concerning the new structures, their bioactivities, including neuroprotective, anti-inflammatory, antioxidant, antibacterial and antivirus, cytotoxic, immunomodulatory, and enzyme inhibitory effects, and pharmacokinetic properties.

  2. Paniculatumoside G, a new C21 steroidal glycoside from Cynanchum paniculatum

    Directory of Open Access Journals (Sweden)

    Hua Gao

    Full Text Available ABSTRACT A new C21 steroidal glycoside, paniculatumoside G, together with neocynapanogenin C isolated for the first time from the natural source and two known compounds were isolated and characterized from the roots and rhizomes of Cynanchum paniculatum (Bunge Kitag. ex H.Hara, Apocynaceae, a commonly used Traditional Chinese Medicine. On the basis of spectroscopic analysis, including HR-ESI-MS, 1D and 2D NMR spectral data, the structure of the new C21 steroidal glycoside was elucidated as neocynapanogenin H 3-O-β-D-oleandropyranoside.

  3. Two minor diterpene glycosides and an eudesman sesquiterpene from Coleus forskohlii.

    Science.gov (United States)

    Shan, Yupei; Wang, Xiaobing; Zhou, Xiang; Kong, Lingyi; Niwa, Masatake

    2007-03-01

    Two new labdane diterpene glycosides, forskoditerpenosides A, B (1, 2) and a new eudesmane sesquiterpene, 4beta,7beta,11-enantioeudesmantriol (3), were isolated from the ethanol extract of the whole plant of Coleus forskohlii. Their structures and stereochemistry were elucidated by extensive spectroscopic analysis and chemical methods. The structure of compound 3 was confirmed by X-ray diffraction. This is the first report about the occurrence of glycosides derived from the kind of labdane diterpene, 8,13-epoxy-labd-14-en-11-one, in the nature. Compounds 1 and 2 showed relaxative effects on isolated guinea pig tracheal spirals in vitro.

  4. Synthesis of O- and C-glycosides derived from β-(1,3)-D-glucans.

    Science.gov (United States)

    Marca, Eduardo; Valero-Gonzalez, Jessika; Delso, Ignacio; Tejero, Tomás; Hurtado-Guerrero, Ramon; Merino, Pedro

    2013-12-15

    A series of β-(1,3)-d-glucans have been synthesized incorporating structural variations specifically on the reducing end of the oligomers. Both O- and C-glucosides derived from di- and trisaccharides have been obtained in good overall yields and with complete selectivity. Whereas the O-glycosides were obtained via a classical Koenigs-Knorr glycosylation, the corresponding C-glycosides were obtained through allylation of the anomeric carbon and further cross-metathesis reaction. Finally, the compounds were evaluated against two glycosidases and two endo-glucanases and no inhibitory activity was observed. Copyright © 2013 Elsevier Ltd. All rights reserved.

  5. Phenylethanoid Glycosides: Research Advances in Their Phytochemistry, Pharmacological Activity and Pharmacokinetics

    Directory of Open Access Journals (Sweden)

    Zhenzhen Xue

    2016-07-01

    Full Text Available Phenylethanoid glycosides (PhGs are widely distributed in traditional Chinese medicines as well as in other medicinal plants, and they were characterized by a phenethyl alcohol (C6-C2 moiety attached to a β-glucopyranose/β-allopyranose via a glycosidic bond. The outstanding activity of PhGs in diverse diseases proves their importance in medicinal chemistry research. This review summarizes new findings on PhGs over the past 10 years, concerning the new structures, their bioactivities, including neuroprotective, anti-inflammatory, antioxidant, antibacterial and antivirus, cytotoxic, immunomodulatory, and enzyme inhibitory effects, and pharmacokinetic properties.

  6. Two new monoterpenoid glycosides from the fresh rhizome of Tongling White Ginger (Zingiber officinale).

    Science.gov (United States)

    Guo, Tao; Tan, Su-Bei; Wang, Ya; Chang, Jun

    2018-01-01

    Two new monoterpenoid glycosides, trans-1,8-cineole-3,6-dihydroxy-3-O-β-D-glucopyranoside (1), and 5,9-dihydroxy borneol 2-O-β-D-glucopyranoside (2), together with four known monoterpenoid glycosides (3-6), were isolated from the water-soluble constituents of the fresh rhizome of Tongling White Ginger (Zingiber officinale). Their structures were decisively elucidated by spectroscopic analysis. In vitro tests for antimicrobial activity showed that compounds 1 and 3 possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Staphylococcus epidermidis.

  7. Simultaneous determination of iridoid glycosides, phenethylalcohol glycosides and furfural derivatives in Rehmanniae Radix by high performance liquid chromatography coupled with triple-quadrupole mass spectrometry

    DEFF Research Database (Denmark)

    Xu, Jun; Wu, Jie; Zhu, Ling-Ying

    2012-01-01

    spectrometry (HPLC–TQ-MS) was developed. The sample preparation was executed using an optimised ultrasonic method with complete extraction efficiencies of eight analytes. For mass spectrometry, selected ion recording (SIR) scan mode was used to improve the sensitivity and selectivity. The established method......In this study, a sensitive and selective method for simultaneously quantifying eight major components (four iridoid glycosides, three phenethylalcohol glycosides and one furfural derivative) of Rehmanniae Radix by high performance liquid chromatography coupled with triple-quadrupole mass...... was validated in terms of linearity, sensitivity, precision, accuracy and stability, and successfully applied to determine the contents of the eight analytes in different batches of raw and processed Rehmanniae Radix, which confirmed that the established method was reliable and useful for “holistic” quality...

  8. Preparative isolation and purification of five flavonoid glycosides and one benzophenone galloyl glycoside from Psidium guajava by high-speed counter-current chromatography (HSCCC).

    Science.gov (United States)

    Zhu, Yindi; Liu, Yue; Zhan, Ying; Liu, Lin; Xu, Yajuan; Xu, Tunhai; Liu, Tonghua

    2013-12-16

    Psidium guajava leaves have a diverse phytochemical composition including flavonoids, phenolics, meroterpenoids and triterpenes, responsible for the biological activities of the medicinal parts. In particular, flavonol glycosides show beneficial effects on type II diabetes mellitus. A simple and efficient HSCCC method has been developed for the preparative separation of five flavonoid glycosides and one diphenylmethane glycoside from P. guajava. A solvent system composed of n-hexane-ethyl acetate-methanol-water (0.7:4:0.8:4, v/v/v/v) was optimized for the separation. The upper phase was used as the stationary phase, and the lower phase was used as the mobile phase. Under the optimized conditions, hyperoside (15.3 mg), isoquercitrin (21.1 mg), reynoutrin (65.2 mg), quercetin-3-O-β-D-arabinopyranoside (71.7 mg), quercetin-3-O-α-L-arabinofuranoside (105.6 mg) and 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6''-O-galloyl)-β-D-glucopyranoside (98.4 mg) were separated from crude sample (19.8 g). The structures of all the isolates were identified by ESI-MS, 1H- and 13C-NMR analyses and their purities (>95%) were determined using HPLC.

  9. Preparative Isolation and Purification of Five Flavonoid Glycosides and One Benzophenone Galloyl Glycoside from Psidium guajava by High-Speed Counter-Current Chromatography (HSCCC

    Directory of Open Access Journals (Sweden)

    Yindi Zhu

    2013-12-01

    Full Text Available Psidium guajava leaves have a diverse phytochemical composition including flavonoids, phenolics, meroterpenoids and triterpenes, responsible for the biological activities of the medicinal parts. In particular, flavonol glycosides show beneficial effects on type II diabetes mellitus. A simple and efficient HSCCC method has been developed for the preparative separation of five flavonoid glycosides and one diphenylmethane glycoside from P. guajava. A solvent system composed of n-hexane–ethyl acetate–methanol–water (0.7:4:0.8:4, v/v/v/v was optimized for the separation. The upper phase was used as the stationary phase, and the lower phase was used as the mobile phase. Under the optimized conditions, hyperoside (15.3 mg, isoquercitrin (21.1 mg, reynoutrin (65.2 mg, quercetin-3-O-β-D-arabinopyranoside (71.7 mg, quercetin-3-O-α-L-arabinofuranoside (105.6 mg and 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6''-O-galloyl-β-D-glucopyranoside (98.4 mg were separated from crude sample (19.8 g. The structures of all the isolates were identified by ESI-MS, 1H- and 13C-NMR analyses and their purities (>95% were determined using HPLC.

  10. Tareciliosides H-M: further cycloartane glycosides from leaves of Tarenna gracilipes.

    Science.gov (United States)

    Zhao, Zhimin; Matsunami, Katsuyoshi; Otsuka, Hideaki; Shinzato, Takakazu; Takeda, Yoshio

    2011-01-01

    From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Tarenna gracilipes, collected in Okinawa, six further new cycloartane glycosides, named tareciliosides H-M (1-6), were isolated. Their structures were established through a combination of spectroscopic analyses.

  11. Medicinal flowers. XXX. Eight new glycosides, everlastosides F-M, from the flowers of Helichrysum arenarium.

    Science.gov (United States)

    Morikawa, Toshio; Wang, Li-Bo; Ninomiya, Kiyofumi; Nakamura, Seikou; Matsuda, Hisashi; Muraoka, Osamu; Wu, Li-Jun; Yoshikawa, Masayuki

    2009-08-01

    Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.

  12. Synthesis and evaluation of cardiac glycoside mimics as potential anticancer drugs

    DEFF Research Database (Denmark)

    Jensen, Marie; Schmidt, Steffen; Fedosova, Natalya

    2011-01-01

    recent years cardiac glycosides have furthermore been suggested to possess valuable anticancer activity. To mimic the labile trisaccharide of digitoxin with a stabile carbohydrate surrogate, we have used sulfur linked ethylene glycol moieties of varying length (mono-, di-, tri- or tetra-ethylene glycol...

  13. Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades.

    Science.gov (United States)

    Bahrami, Yadollah; Franco, Christopher M M

    2016-08-04

    Sea cucumbers have been valued for many centuries as a tonic and functional food, dietary delicacies and important ingredients of traditional medicine in many Asian countries. An assortment of bioactive compounds has been described in sea cucumbers. The most important and abundant secondary metabolites from sea cucumbers are triterpene glycosides (saponins). Due to the wide range of their potential biological activities, these natural compounds have gained attention and this has led to their emergence as high value compounds with extended application in nutraceutical, cosmeceutical, medicinal and pharmaceutical products. They are characterized by bearing a wide spectrum of structures, such as sulfated, non-sulfated and acetylated glycosides. Over 700 triterpene glycosides have been reported from the Holothuroidea in which more than 145 are decorated with an acetoxy group having 38 different aglycones. The majority of sea cucumber triterpene glycosides are of the holostane type containing a C18 (20) lactone group and either Δ(7(8)) or Δ(9(11)) double bond in their genins. The acetoxy group is mainly connected to the C-16, C-22, C-23 and/or C-25 of their aglycone. Apparently, the presence of an acetoxy group, particularly at C-16 of the aglycone, plays a significant role in the bioactivity; including induction of caspase, apoptosis, cytotoxicity, anticancer, antifungal and antibacterial activities of these compounds. This manuscript highlights the structure of acetylated saponins, their biological activity, and their structure-activity relationships.

  14. Early O-glycosidic glycosylation of proglucagon in pancreatic islets: an unusual type of prohormonal modification.

    Science.gov (United States)

    Patzelt, C; Weber, B

    1986-01-01

    Proglucagon from rat islets is identified as a glycoprotein by its binding to soybean lectin and by the biosynthetic incorporation of [14C]galactosamine. Glycosylation can be demonstrated for both forms of proglucagon, i.e. the primary translation product which is detectable as early as 30 s after incubation of isolated islets with radioactive amino acids (proglucagon a), and its conversion product of slightly higher electrophoretic mobility which is formed after 5-10 min of incubation (proglucagon b). This glycosylation is determined to be of the O-glycosidic type by the following criteria: rat proglucagon has previously been shown to lack an acceptor sequence for N-glycosidic linkage of sugars, the sugar bond in rat proglucagon is labile under mild alkaline conditions, glycosylated serine is demonstrated in proteolytic lysates of both the early and the late form of this prohormone. O-glycosidic linkage of sugars has not been reported for other prohormones. Its early formation and the apparent absence of N-glycosidically bound sugars in proglucagon give evidence for an unusual type of protein glycosylation. Images Fig. 1. Fig. 2. Fig. 3. Fig. 4. Fig. 5. PMID:3096715

  15. A Review on the Pharmacology and Toxicology of Steviol Glycosides Extracted from Stevia rebaudiana.

    Science.gov (United States)

    Momtazi-Borojeni, Amir Abbas; Esmaeili, Seyed-Alireza; Abdollahi, Elham; Sahebkar, Amirhossein

    2017-01-01

    Stevia rebaudiana Bertoni is a sweet and nutrient-rich plant belonging to the Asteraceae family. Stevia leaves contain steviol glycosides including stevioside, rebaudioside (A to F), steviolbioside, and isosteviol, which are responsible for the plant's sweet taste, and have commercial value all over the world as a sugar substitute in foods, beverages and medicines. Among the various steviol glycosides, stevioside, rebaudioside A and rebaudioside C are the major metabolites and these compounds are on average 250-300 times sweeter than sucrose. Steviol is the final product of Stevia metabolism. The metabolized components essentially leave the body and there is no accumulation. Beyond their value as sweeteners, Stevia and its glycosdies possess therapeutic effects against several diseases such as cancer, diabetes mellitus, hypertension, inflammation, cystic fibrosis, obesity and tooth decay. Studies have shown that steviol glycosides found in Stevia are not teratogenic, mutagenic or carcinogenic and cause no acute and subacute toxicity. The present review provides a summary on the biological and pharmacological properties of steviol glycosides that might be relevant for the treatment of human diseases. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  16. Isolation, Characterization, and Surfactant Properties of the Major Triterpenoid Glycosides from Unripe Tomato Fruits

    NARCIS (Netherlands)

    Yamanaka, T.; Vincken, J.P.; Waard, de P.; Sanders, M.G.; Takada, N.; Gruppen, H.

    2008-01-01

    Various triterpenoid glycosides were extracted from whole unripe tomato fruits (Lycopersicon esculentum cv. Cedrico), using aqueous 70% (v/v) ethanol to study their surfactant properties. Cation-exchange chromatography using a Source 15S column and subsequent semipreparative HPLC using an XTerra

  17. Thermus thermophilus Glycoside Hydrolase Family 57 Branching Enzyme : Crystal Structure, Mechanism of Action, and Products Formed

    NARCIS (Netherlands)

    Palomo, Marta; Pijning, Tjaard; Booiman, Thijs; Dobruchowska, Justyna M.; Vlist, Jeroen van der; Kralj, Slavko; Planas, Antoni; Loos, Katja; Kamerling, Johannis P.; Dijkstra, Bauke W.; Maarel, Marc J.E.C. van der; Dijkhuizen, Lubbert; Leemhuis, Hans

    2011-01-01

    Branching enzyme (EC 2.4.1.18; glycogen branching enzyme; GBE) catalyzes the formation of alpha 1,6-branching points in glycogen. Until recently it was believed that all GBEs belong to glycoside hydrolase family 13 (GH13). Here we describe the cloning and expression of the Thermus thermophilus

  18. Bioavailability of genistein, daidzein, and their glycosides in intestinal epithelial Caco-2 cells

    NARCIS (Netherlands)

    Steensma, A.; Noteborn, H.P.J.M.; Jagt, van der R.C.M.; Polman, Th.H.G.; Mengelers, M.J.B.; Kuiper, H.A.

    1999-01-01

    In this study information was obtained on bioavailability of genistein, daidzein and their glycosides in human intestinal epithelial Caco-2 cells grown on semi-permeable filters. The integrity of Caco-2 monolayers was confirmed by transepithelial electrical resistance measurements and by

  19. A Novel Diterpene Glycoside with Nine Glucose Units from Stevia rebaudiana Bertoni

    Directory of Open Access Journals (Sweden)

    Indra Prakash

    2017-01-01

    Full Text Available Following our interest in new diterpene glycosides with better taste profiles than that of Rebaudioside M, we have recently isolated and characterized Rebaudioside IX—a novel steviol glycoside—from a commercially‐supplied extract of Stevia rebaudiana Bertoni. This molecule contains a hexasaccharide group attached at C‐13 of the central diterpene core, and contains three additional glucose units when compared with Rebaudioside M. Here we report the complete structure elucidation—based on extensive Nuclear Magnetic Resonance (NMR analysis (1H, 13C, Correlation Spectroscopy (COSY, Heteronuclear Single Quantum Coherence‐Distortionless Enhancement Polarization Transfer (HSQC‐DEPT, Heteronuclear Multiple Bond Correlation (HMBC, 1D Total Correlation Spectroscopy (TOCSY, Nuclear Overhauser Effect Spectroscopy (NOESY and mass spectral data—of this novel diterpene glycoside with nine sugar moieties and containing a relatively rare 16 α‐linked glycoside. A steviol glycoside bearing nine glucose units is unprecedented in the literature, and could have an impact on the natural sweetener catalog.

  20. Structure elucidation and complete NMR spectral assignments of new furostanol glycosides from Solanum torvum.

    Science.gov (United States)

    Lu, Yuanyuan; Luo, Jianguang; Kong, Lingyi

    2009-09-01

    Two new furostanol glycosides, torvosides O (1) and P (2), were isolated from leaves of Solanum torvum. Their structures were completely and unambiguously assigned by one- and two-dimensional NMR techniques ((1)H NMR, (13)C NMR, TOCSY, HSQC, ROESY and HMBC), ESI-MS spectrometry and chemical methods. Copyright (c) 2009 John Wiley & Sons, Ltd.

  1. Effect of different drying methods on the composition of steviol glycosides in Stevia rebaudiana Bertoni leaves

    Science.gov (United States)

    Aranda-González, Irma; Betancur-Ancona, David; Chel-Guerrero, Luis; Moguel-Ordóñez, Yolanda

    2017-01-01

    Drying techniques can modify the composition of certain plant compounds. Therefore, the aim of the study was to assess the effect of different drying methods on steviol glycosides in Stevia rebaudiana Bertoni leaves. Four different drying methods were applied to Stevia rebaudiana Bertoni leaves, which were then subjected to aqueous extraction. Radiation or convection drying was performed in stoves at 60°C, whereas shade or sun drying methods were applied at 29.7°C and 70% of relative humidity. Stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, dulcoside A, and steviolbioside were quantified by a validated HPLC method. Among steviol glycosides, the content (g 100 g-1 dry basis) of stevioside, rebaudioside A, rebaudioside B, and rebaudioside C varied according to the drying method. The total glycoside content was higher in sun-dried samples, with no significant differences compared to shade or convection drying, whereas radiation drying adversely affected the content of rebaudioside A and rebaudioside C (p <0.01) and was therefore a method lowering total glycoside content. The effect of the different drying methods was also reflected in the proportion of the sweetener profile. Convection drying could be suitable for modern food processing industries while shadow or sun drying may be a low-cost alternative for farmers.

  2. Synthesis of Some Phenylpropanoid Glycosides (PPGs and Their Acetylcholinesterase/Xanthine Oxidase Inhibitory Activities

    Directory of Open Access Journals (Sweden)

    Jin-Hui Wang

    2011-04-01

    Full Text Available In this research, three categories of phenylpropanoid glycosides (PPGs were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE and xanthine oxidase (XOD were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.

  3. Enhancement of production of eugenol and its glycosides in transgenic aspen plants via genetic engineering.

    Science.gov (United States)

    Koeduka, Takao; Suzuki, Shiro; Iijima, Yoko; Ohnishi, Toshiyuki; Suzuki, Hideyuki; Watanabe, Bunta; Shibata, Daisuke; Umezawa, Toshiaki; Pichersky, Eran; Hiratake, Jun

    2013-06-21

    Eugenol, a volatile phenylpropene found in many plant species, exhibits antibacterial and acaricidal activities. This study attempted to modify the production of eugenol and its glycosides by introducing petunia coniferyl alcohol acetyltransferase (PhCFAT) and eugenol synthase (PhEGS) into hybrid aspen. Gas chromatography analyses revealed that wild-type hybrid aspen produced small amount of eugenol in leaves. The heterologous overexpression of PhCFAT alone resulted in up to 7-fold higher eugenol levels and up to 22-fold eugenol glycoside levels in leaves of transgenic aspen plants. The overexpression of PhEGS alone resulted in a subtle increase in either eugenol or eugenol glycosides, and the overexpression of both PhCFAT and PhEGS resulted in significant increases in the levels of both eugenol and eugenol glycosides which were nonetheless lower than the increases seen with overexpression of PhCFAT alone. On the other hand, overexpression of PhCFAT in transgenic Arabidopsis and tobacco did not cause any synthesis of eugenol. These results indicate that aspen leaves, but not Arabidopsis and tobacco leaves, have a partially active pathway to eugenol that is limited by the level of CFAT activity and thus the flux of this pathway can be increased by the introduction of a single heterologous gene. Copyright © 2013 Elsevier Inc. All rights reserved.

  4. Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits

    Science.gov (United States)

    Bioassay-guided isolation and purification of the ethyl acetate extract of Moringa oleifera fruits yielded three new phenolic glycosides; 4-[(2'-O-acetyl-a-L-rhamnosyloxy) benzyl]isothiocyanate (1), 4-[(3'-O-acetyl-a-L-rhamnosyloxy)benzyl]isothiocyanate (2), and S-methyl-N-{4-[(a-L-rhamnosyloxy)benz...

  5. Dopaol 2-keto- and 2,3-diketo-glycosides from Chelone obliqua (Scrophulariaceae)

    DEFF Research Database (Denmark)

    Franzyk, Henrik; Olsen, Carl Erik; Jensen, Søren Rosendal

    2004-01-01

    Two unique 2-(3,4-dihydroxyphenyl)ethyl glycosides, namely, dopaol beta-D-2-ketoglucopyranoside and dopaol beta-D-2,3-diketoglucopyranoside, were isolated from Chelone obliqua together with the iridoid glucoside catalpol, dopaol beta-D-glucopyranoside, descaffeoylverbascoside, and verbascoside. G...

  6. Total Synthesis of Linckosides A and B, the Representative Starfish Polyhydroxysteroid Glycosides with Neuritogenic Activities.

    Science.gov (United States)

    Zhu, Dapeng; Yu, Biao

    2015-12-09

    Linckosides A and B, two starfish metabolites with promising neuritogenic activities, are synthesized in a longest linear sequence of 32 steps and 0.5% overall yield; this represents the first synthesis of members of the polyhydroxysteroid glycoside family, which occur widely in starfishes.

  7. Iridoid and phenylethanoid glycosides in the New Zealand sun hebes (Veronica; Plantaginaceae)

    DEFF Research Database (Denmark)

    Taskova, Rilka M.; Kokubun, Tetsuo; Garnock-Jones, Phil J.

    2012-01-01

    The sun hebes are a small clade of New Zealand Veronica formerly classified as Heliohebe. The water-soluble compounds of Veronica pentasepala, Veronica raoulii and Veronica hulkeana were studied and 30 compounds including 15 iridoid glucosides, 12 phenylethanoid glycosides, the acetophenone gluco...

  8. In vitro tocolytic effects of the glycosidic constituents of the fruits of ...

    African Journals Online (AJOL)

    The tocolytic effect of the butanol fraction of the glycoside extract of the fruits of Piper guineense, was pharmacologically screened by measuring the uterine contractility. A state of oestrous was induced in three female rats through intramuscular injection of 0.1 μg per 100 g body weight of stilboestrol. The animals were ...

  9. Study on anti-tumor effect of total glycosides from radix paeoniae ...

    African Journals Online (AJOL)

    The objective of the paper was to study the anti-tumor effect of total glycosides from Radix paeoniae rubra in S180 tumor-bearing mice, and to preliminarily explore its mechanism of action. Mice were made into S180 solid tumor model, grouped and administered with the extracts; tumor inhibition rate was measured by ...

  10. Phenylethanoid and iridoid glycosides in the New Zealand snow hebes (Veronica, Plantaginaceae)

    DEFF Research Database (Denmark)

    Taskova, Rilka M.; Kokubun, Tetsuo; Ryan, Ken G.

    2010-01-01

    of phenylethanoid glycosides were elucidated by spectroscopic analyses. Further, eight known phenylethanoids, nine iridoids, 6'-feruloyl-sucrose and mannitol are also reported. It was found that the iridoid profile of the snow hebes was different from the other species of Veronica in New Zealand but similar...

  11. Synthesis of glycosyl fluorides from (phenylthio)glycosides using IF5-pyridine-HF.

    Science.gov (United States)

    Kunigami, Masataka; Hara, Shoji

    2015-11-19

    IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio)glycosides. Common protecting groups of alcohol and diol can tolerate the reaction conditions performed, and therefore, the present method is applicable to the synthesis of various glycosyl fluorides. Copyright © 2015 Elsevier Ltd. All rights reserved.

  12. Extraction of steviol glycosides from fresh Stevia using acidified water; clarification followed by ultrafiltration and nanofiltration

    NARCIS (Netherlands)

    Kootstra, A.M.J.; Elissen, H.J.H.; Huurman, Sander

    2016-01-01

    As part of the PPS Kleinschalige bioraffinage project (WP1b), fresh Stevia material was used in the extraction of steviol glycosides using water acidified through conversion of sugar by microorganisms naturally present on the plant. Two successive harvests from the same plot were used. Previous

  13. Identification, Quantification, and Sensory Characterization of Steviol Glycosides from Differently Processed Stevia rebaudiana Commercial Extracts

    NARCIS (Netherlands)

    Espinoza, M.I.; Vincken, J.P.; Sanders, M.G.; Castro, C.; Stieger, M.A.; Agosin, E.

    2014-01-01

    Stevia rebaudiana is known for its sweet-tasting ent-kaurene diterpenoid glycosides. Several manufacturing strategies are currently employed to obtain Stevia sweeteners with the lowest possible off-flavors. The chemical composition of four commercial S. rebaudiana extracts, obtained by different

  14. The influence of stevia glycosides on the growth of Lactobacillus reuteri strains.

    Science.gov (United States)

    Deniņa, I; Semjonovs, P; Fomina, A; Treimane, R; Linde, R

    2014-03-01

    Use of stevia-derived sweeteners was recently officially approved by the European Commission, and their application in the food industry has increased, especially in functional foods. However, there are scarce data about the influence of stevia on probiotic bacteria, which are important both as an inhabitant of the human gut and as a functional food additive. Taking into consideration the broad application of Lactobacillus reuteri in functional foods, the aim of the research was to evaluate the influence of stevia glycosides on its growth. Six Lact. reuteri strains were tested for their ability to grow in the presence of stevioside and rebaudioside A (0·2-2·6 g l(-1) ). The effect of stevia glycosides on biomass concentration, cell count, pH and lactic and acetic acid synthesis was analysed. Both glycosides impaired the growth of analysed strains. However, the inhibitory effect was strain specific, and the concentration-dependent effect was not observed for all parameters. The most pronounced concentration-dependent effect was on lactic and acetic acid production. Taking into account the observed strain-specific inhibitory effect of stevia glycosides, it could be suggested to evaluate the influence of them on each strain employed before their simultaneous application in functional foods. The study showed that the growth of Lactobacillus reuteri strains was inhibited in the presence of stevia sweeteners stevioside and rebaudioside A. Probiotics, for example Lact. reuteri strains, are often used as functional additives in health foods and are an important natural inhabitant of the human gastrointestinal tract. Stevia glycosides application in food is increasing; yet, there are no data about the influence of stevia glycosides on Lact. reuteri growth and very few data on growth of other lactobacilli, either in probiotic foods or in the gastrointestinal tract. This research shows that it is necessary to evaluate the influence of stevia glycosides on other groups

  15. Immunoaffinity Knockout of Saponin Glycosides from Asparagus racemosus to Assess Anti-lipid Peroxidation.

    Science.gov (United States)

    Onlom, Churanya; Phrompittayarat, Watoo; Putalun, Waraporn; Waranuch, Neti; Ingkaninan, Kornkanok

    2017-07-01

    Asparagus racemosus Willd (Asparagaceae family), known as Shatavari, is important in Ayurveda and traditional Thai medicines. The saponin glycosides, shatavarin I and IV are major constituents in its roots and may be responsible for their actions including protection against lipid peroxidation and carcinogenesis. To develop an immunoaffinity column for isolating compounds with structures related to shatavarin IV from crude extracts of A. racemosus root. The monoclonal antibody recognising shatavarin IV (mAbShavIV) was coupled to an Affi-Gel Hz gel to isolate compounds with structures related to shatavarin IV from the other components of crude extracts of A. racemosus root. The saponin glycosides in each fraction were analysed by mAbShavIV ELISA and LC-MS/MS. The pooled wash-through fractions contained 3% of loaded mAbShavIV reactive saponin glycosides, while eluted fractions released ~ 90% of shatavarin saponin glycosides in a single step. Using thiobarbiturate (TBARs) to measure lipid-peroxidation, the extract, and the pooled wash-through fractions showed moderate protection against Cu+ -induced oxidation of human low density lipoprotein (LDL) (IC50 11.3 ± 1.4 and 12.6 ± 0.9 μg/mL, respectively). In contrast, the saponin glycosides eluted from the mAbShavIV-column had weaker protectant (IC50 29.7 ± 1.8 μg/mL) suggesting that A. racemosus shatavarins do not inhibit carcinogenesis through preventing lipid peroxidation. The strategy described here demonstrates its utility for isolating a group of related compounds from the rest of the extract with selectivity and recovery rate. Pharmacological efficacy and synergistic effects of the components obtained can be further investigated. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  16. Supplementing with non-glycoside hydrolase proteins enhances enzymatic deconstruction of plant biomass.

    Directory of Open Access Journals (Sweden)

    Xiaoyun Su

    Full Text Available The glycoside hydrolases (GH of Caldicellulosiruptor bescii are thermophilic enzymes, and therefore they can hydrolyze plant cell wall polysaccharides at high temperatures. Analyses of two C. bescii glycoside hydrolases, CbCelA-TM1 and CbXyn10A with cellulase and endoxylanase activity, respectively, demonstrated that each enzyme is highly thermostable under static incubation at 70°C. Both enzymes, however, rapidly lost their enzymatic activities when incubated at 70°C with end-over-end shaking. Since crowding conditions, even at low protein concentrations, seem to influence enzymatic properties, three non-glycoside hydrolase proteins were tested for their capacity to stabilize the thermophilic proteins at high temperatures. The three proteins investigated were a small heat shock protein CbHsp18 from C. bescii, a histone MkHistone1 from Methanopyrus kandleri, and bovine RNase A, from a commercial source. Fascinatingly, each of these proteins increased the thermostability of the glycoside hydrolases at 70°C during end-over-end shaking incubation, and this property translated into increases in hydrolysis of several substrates including the bioenergy feedstock Miscanthus. Furthermore, MkHistone1 and RNase A also altered the initial products released from the cello-oligosaccharide cellopentaose during hydrolysis with the cellodextrinase CbCdx1A, which further demonstrated the capacity of the three non-GH proteins to influence hydrolysis of substrates by the thermophilic glycoside hydrolases. The non-GH proteins used in the present report were small proteins derived from each of the three lineages of life, and therefore expand the space from which different polypeptides can be tested for their influence on plant cell wall hydrolysis, a critical step in the emerging biofuel industry.

  17. Turbo-extraction of glycosides from Stevia rebaudiana using a fractional factorial design

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    Paula M. Martins

    Full Text Available ABSTRACT Stevia rebaudiana (Bertoni Bertoni, Asteraceae, leaf extract has recently called the attention of food industry as a proposal for natural sweetener. The sweet flavor is attributed to the glycosides, in especial stevioside and rebaudioside A, which are the plant main chemical markers. The aim of the work reported here was to optimize the turbo-extraction of stevia leaves using water, ethanol 70% and 90% (w/w as green solvents. A 25-2 factorial design was applied to study the linear effects of the drug size, solvent to drug ratio, temperature, time and also the turbolysis speed on the extraction of glycosides. The glycosides exhaustive extraction showed that ethanol 70% gave better results and was used for turbo-extraction. The stevioside and rebaudioside A contents were quantified by a validated method by high performance liquid chromatographic with photodiode array detector. The contents of stevioside and rebaudioside A in fluid extract increased with the drug size, but decreased at high shearing speeds and solvent to drug ratio, while their yields decreased at higher temperature and were not affected by turbo speed. An increase in solvent to drug ratio reduced significantly the glycosides percent in dried extract. Optimal solution for S. rebaudiana leaves turbo-extraction was determined by desirability functions. The optimal extraction condition corresponded to drug size of 780 µm, solvent to drug ratio of 10, extraction time of 18 min; temperature of 23 ºC and turbo speed of 20,000 rpm, resulting in yields of 4.98% and 2.70%, for stevioside and rebaudioside A, respectively. These yields are comparable to the ones recently published for dynamic maceration, but with the advantage of shorter extraction times. This work demonstrates that turbolysis is promising for S. rebaudiana glycosides extraction and stimulate new research on the purification of these extracts, which may become an interesting source of income for developing

  18. Influence of Linkage Stereochemistry and Protecting Groups on Glycosidic Bond Stability of Sodium Cationized Glycosyl Phosphates

    Science.gov (United States)

    Zhu, Y.; Yang, Zhihua; Rodgers, M. T.

    2017-09-01

    Energy-resolved collision-induced dissociation (ER-CID) experiments of sodium cationized glycosyl phosphate complexes, [GP x +Na]+, are performed to elucidate the effects of linkage stereochemistry (α versus β), the geometry of the leaving groups (1,2-cis versus 1,2-trans), and protecting groups (cyclic versus non-cyclic) on the stability of the glycosyl phosphate linkage via survival yield analyses. A four parameter logistic dynamic fitting model is used to determine CID50% values, which correspond to the level of rf excitation required to produce 50% dissociation of the precursor ion complexes. Present results suggest that dissociation of 1,2-trans [GP x +Na]+ occurs via a McLafferty-type rearrangement that is facilitated by a syn orientation of the leaving groups, whereas dissociation of 1,2-cis [GPx+Na]+ is more energetic as it involves the formation of an oxocarbenium ion intermediate. Thus, the C1-C2 configuration plays a major role in determining the stability/reactivity of glycosyl phosphate stereoisomers. For 1,2-cis anomers, the cyclic protecting groups at the C4 and C6 positions stabilize the glycosidic bond, whereas for 1,2-trans anomers, the cyclic protecting groups at the C4 and C6 positions tend to activate the glycosidic bond. The C3 O-benzyl (3 BnO) substituent is key to determining whether the sugar or phosphate moiety retains the sodium cation upon CID. For 1,2-cis anomers, the 3 BnO substituent weakens the glycosidic bond, whereas for 1,2-trans anomers, the 3 BnO substituent stabilizes the glycosidic bond. The C2 O-benzyl substituent does not significantly impact the glycosidic bond stability regardless of its orientation. [Figure not available: see fulltext.

  19. Deuterium NMR Investigation of the lyotropic phases of alkyl β-glycoside/D2O systems.

    Science.gov (United States)

    Misran, Omar; Timimi, Bakir A; Heidelberg, Thorsten; Sugimura, Akihiko; Hashim, Rauzah

    2013-06-20

    We have investigated the phase behavior of four glycosides (βC8OGlc, βC8SGlc, βC10OGlc, βC8OGal) in water and D2O by optical polarizing microscopy and deuterium NMR. Previously published phase diagrams were evaluated by deuterium NMR, via monitoring D2O spectra, and confirmed the presence of the hexagonal, bicontinuous cubic, and lamellar phases in these glycosides. We have also shown the presence of the gel phase in (βC10OGlc) and observed the extensive supercooling of the lamellar phase to temperatures well below the Kraft line. While the main features of the phase diagrams were confirmed, some phase boundaries were found to be slightly different. Magnetically aligned spectra were also observed for relatively dilute samples for the hexagonal phase (βC8OGlc and βC8OGal) and the lamellar phase (βC8SGlc and βC10OGlc). The average number of bound water molecules per headgroup in the lamellar phase for the glycosides was determined by the systematic measurement of the quadrupolar splitting of D2O over a wide range of values of the (glycoside/water) molar ratio. The number of water molecules bound to the headgroup was found on average to be about 1.6-1.7 water molecules with no significant differences in this value for the different glycosides (and over the temperature range investigated), indicating that the bound water content is predominately influenced by the number of hydroxyl groups of the headgroup only. However, this bound water content of only 1.6-1.7 water molecules per sugar headgroup is surprisingly low, suggesting strong intermolecular interactions of the OH groups of headgroup sugars. The results are in line with computational results reported earlier for the octyl-β-glucoside and β-galactoside, which show the presence of strong intralayer hydrogen bonding.

  20. Saccharomyces cerevisiae and Kluyveromyces marxianus Cocultures Allow Reduction of Fermentable Oligo-, Di-, and Monosaccharides and Polyols Levels in Whole Wheat Bread.

    Science.gov (United States)

    Struyf, Nore; Laurent, Jitka; Verspreet, Joran; Verstrepen, Kevin J; Courtin, Christophe M

    2017-10-04

    Fermentable oligo-, di-, and monosaccharides and polyols (FODMAPs) are small molecules that are poorly absorbed in the small intestine and rapidly fermented in the large intestine. There is evidence that a diet low in FODMAPs reduces abdominal symptoms in approximately 70% of the patients suffering from irritable bowel syndrome. Wheat contains relatively high fructan levels and is therefore a major source of FODMAPs in our diet. In this study, a yeast-based strategy was developed to reduce FODMAP levels in (whole wheat) bread. Fermentation of dough with an inulinase-secreting Kluyveromyces marxianus strain allowed to reduce fructan levels in the final product by more than 90%, while only 56%  reduction was achieved when a control Saccharomyces cerevisiae strain was used. To ensure sufficient CO 2 production, cocultures of S. cerevisiae and K. marxianus were prepared. Bread prepared with a coculture of K. marxianus and S. cerevisiae had fructan levels ≤0.2% dm, and a loaf volume comparable with that of control bread. Therefore, this approach is suitable to effectively reduce FODMAP levels in bread.

  1. Coagulant Activity of Water-Soluble Moringa oleifera Lectin Is Linked to Lowering of Electrical Resistance and Inhibited by Monosaccharides and Magnesium Ions.

    Science.gov (United States)

    de Moura, Kézia Santana; da Silva, Hugo Rafael Chaves; Dornelles, Leonardo Prezzi; Coelho, Luana Cassandra Breitenbach Barroso; Napoleão, Thiago Henrique; de Oliveira, Maria Danielly Lima; Paiva, Patrícia Maria Guedes

    2016-12-01

    Moringa oleifera seeds contain a water-soluble lectin [water-soluble M. oleifera lectin (WSMoL)] that has shown coagulant activity. Magnesium ions are able to interfere with the ability of this lectin to bind carbohydrates. In this study, we performed structural characterization of WSMoL and analyzed its effect on the electrical resistance of a kaolin clay suspension in both presence and absence of monosaccharides (N-acetylglucosamine, glucose, or fructose) and magnesium ions. The coagulant activity of WSMoL was monitored by measuring optical density and electrical resistance over a period of 60 min. Native WSMoL had a molecular mass of 60 kDa and exhibited anionic nature (pI 5.5). In sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), it appeared as three polypeptide bands of 30, 20, and 10 kDa. WSMoL reduced the optical density and electrical resistance of the kaolin suspension, which suggests that suspended particles are destabilized and that this is followed by formation of complexes. The coagulant activity of lectin decreased in the presence of Mg2+ ions and carbohydrates at concentrations that also inhibited hemagglutinating activity. This was most likely due to conformational changes in lectin structure. Our findings suggest that the coagulant activity of WSMoL is enhanced by lowering of electrical resistance of the medium and is impaired by lectin-carbohydrate and lectin-Mg2+ interactions.

  2. Revisiting the planarity of nucleic acid bases: Pyramidilization at glycosidic nitrogen in purine bases is modulated by orientation of glycosidic torsion

    Czech Academy of Sciences Publication Activity Database

    Sychrovský, Vladimír; Foldynová-Trantírková, Silvie; Špačková, Naďa; Robeyns, K.; Meervelt van, L.; Blankenfeldt, W.; Vokáčová, Zuzana; Šponer, Jiří; Trantírek, Lukáš

    2009-01-01

    Roč. 37, č. 21 (2009), s. 7321-7331 ISSN 0305-1048 R&D Projects: GA AV ČR(CZ) IAA400040802; GA AV ČR IAA400550701; GA ČR GA203/09/1476; GA MŠk(CZ) LC06030; GA AV ČR KAN200100801 Institutional research plan: CEZ:AV0Z40550506; CEZ:AV0Z60220518; CEZ:AV0Z50040507; CEZ:AV0Z50040702 Keywords : pyrimidalization * glycosidic torion angle Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 7.479, year: 2009

  3. New oleanan-type triterpene and cincholic acid glycosides from Peruvian "Uña de Gato" (Uncaria tomentosa).

    Science.gov (United States)

    Kitajima, Mariko; Hashimoto, Ken-Ichiro; Sandoval, Manuel; Aimi, Norio; Takayama, Hiromitsu

    2004-10-01

    A new oleanan-type triterpene and three new cincholic acid glycosides were isolated from Peruvian "Una de Gato" (Cat's claw, plant of origin: Uncaria tomentosa), a traditional herbal medicine in Peru. Their structures were determined by spectroscopic analysis.

  4. Structures of the novel α-glucosyl linked diterpene glycosides from Stevia rebaudiana.

    Science.gov (United States)

    Chaturvedula, Venkata Sai Prakash; Upreti, Mani; Prakash, Indra

    2011-09-27

    From the commercial extract of the leaves of Stevia rebaudiana, two new minor diterpene glycosides having α-glucosyl linkage were isolated besides the known steviol glycosides including stevioside, steviolbioside, rebaudiosides A-F, rubusoside and dulcoside A. The structures of the two compounds were identified as 13-[(2-O-(3-α-O-d-glucopyranosyl)-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (1), and 13-[(2-O-β-d-glucopyranosyl-3-O-(4-O-α-d-glucopyranosyl)-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (2), on the basis of extensive NMR and MS spectral data as well as chemical studies. Copyright © 2011 Elsevier Ltd. All rights reserved.

  5. Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

    Science.gov (United States)

    Park, Joo-In; Bae, Hae-Rahn; Kim, Chang Gun; Stonik, Valentin; Kwak, Jong-Young

    2014-09-01

    Many marine triterpene glycosides have in vitro and in vivo activities with very low toxicity, suggesting that they are suitable agents for the prevention and treatment of different diseases, particularly cancer. However, the molecular mechanisms of action of natural marine compounds in cancer, immune and other various cells are not fully known. This review focuses on the structural characteristics of marine triterpene glycosides and how these affect their biological activities and molecular mechanisms. In particular, the membranotropic and membranolytic activities of frondoside A and cucumariosides from sea cucumbers and their ability to induce cytotoxicity and apoptosis have been discussed, with a focus on structure-activity relationships. In addition, the structural characteristics and antitumor effects of stichoposide C and stichoposide D have been reviewed along with underlying their molecular mechanisms.

  6. Short communication. Challenges relating to comparison of flavonoid glycosides dissolution profiles from Sutherlandia frutescens products.

    Science.gov (United States)

    Mbamalu, Oluchi N; Syce, James; Samsodien, Halima

    2017-03-01

    Unlike the case of conventional drug formulations, dissolution tests have hitherto not been required for herbal medicinal products commercially available in South Africa. This study investigated dissolution of the South African Sutherlandia frutescens using selected flavonoid glycosides as marker compounds. Dissolution of markers was assessed in three dissolution media at pH 1.2, 4.5 and 6.8, and samples were analysed using a validated HPLC method. The dissolution profile of each marker varied for the different materials investigated. All three media utilised showed differences in flavonoid glycoside dissolution between the S. frutescens products evaluated, with f2 values dissolution from any two of the materials. Dissolution of S. frutescens materials could thus be characterised using the markers in all the media tested. This tool may be employed in the future for comparison of orally administered S. frutescens products, provided between- batch variability is evaluated and found less than between-sample variability.

  7. Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté

    Directory of Open Access Journals (Sweden)

    Taketa Alexandre T. C.

    2004-01-01

    Full Text Available A new triterpenoid glycoside, 3b-O-a-L-arabinopyranosyl rotundic acid, named here mateside (4, and the known triterpenes ursolic acid (1, acetylursolic acid (2, 23-hydroxyursolic acid (3, the saponins ziyu-glycoside I (5 and ilexoside II (6, were isolated from fruits of Ilex paraguariensis. Their structures were established on the basis of 1D and 2D NMR spectroscopic methods. The threshold bitterness values for mateside and ilexoside II were also determined and compared with saponins obtained from leaves of I. paraguariensis and other Ilex species. The high bitterness of Ilexoside II, one of the main saponins found the fruits, but not in the leaves of I. paraguariensis, suggests that the utilization of the fruits in the Maté production can produce a strong taste variation and unknown physiological effects.

  8. [A new oleanane-type triterpenoid glycoside from roots of Ilex asprella].

    Science.gov (United States)

    Wen, Si; Guan, Xi-Feng; Huang, Xiao-Jun; Fan, Chun-Lin; Ye, Wen-Cai; Wang, Ying

    2017-07-01

    A new δ-oleanane-type triterpenoid glycoside, 3-O-(3-O-sulfo)-β-D-glucopyranosiduronic acid 3β-hydroxy-13(18)-oleanen- 28-oic acid 28-β-D-glucopyranosyl ester (1), along with ten known triterpenoid glycosides, rotundinoside A (2), oblonganoside M (3), 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl 3β,19α-dihydroxy-20α- urs-12-en-28-oic acid 28-O-β-D- glucopyranosyl ester (4), ilexsaponin B2 (5), ilexside Ⅱ (6), rotundinoside B (7), ilekudinoside B (8), ilexpublesnin E (9), ilekudinoside D (10) and ilexpernoside D (11), was isolated from the 75% ethanol extract of the roots of Ilex asprella by various chromatographic separation. Their structures were identified on the basis of MS, NMR spectroscopic analysis and chemical methods. In addition, 2-11 were isolated from I. asprella for the first time. Copyright© by the Chinese Pharmaceutical Association.

  9. Direct inhibition of calcineurin by caffeoyl phenylethanoid glycosides from Teucrium chamaedrys and Nepeta cataria.

    Science.gov (United States)

    Prescott, Thomas A K; Veitch, Nigel C; Simmonds, Monique S J

    2011-10-11

    Teucrium chamaedrys L. and Nepeta cataria L. (Lamiaceae) are species with traditional uses that relate to the treatment of inflammation. Extracts of both species were found to inhibit calcineurin; an important regulator of T-cell mediated inflammation that has received little attention in ethnopharmacological research. Extracts and isolated compounds were tested against calcineurin in its calmodulin-activated and basal un-activated state. Active compounds were isolated using Sephadex LH-20 gel filtration and HPLC then identified using NMR spectroscopy. Activity-guided fractionation of Teucrium chamaedrys and Nepeta cataria led to the isolation of the caffeoyl phenylethanoid glycosides teucrioside, verbascoside and lamiuside A (teupolioside). The three compounds inhibited calcineurin both in the presence and absence of calmodulin, suggesting a direct interaction with calcineurin. Calcineurin inhibition should be considered as a potential mode of action when investigating the immunomodulatory activity of caffeoyl phenylethanoid glycoside containing plants. Copyright © 2011 Elsevier Ireland Ltd. All rights reserved.

  10. Phenolic Glycosides from Capsella bursa-pastoris (L. Medik and Their Anti-Inflammatory Activity

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    Joon Min Cha

    2017-06-01

    Full Text Available A new sesquilignan glycoside 1, together with seven known phenolic glycosides 2–8 were isolated from the aerial parts of Capsella bursa-pastoris. The chemical structure of the new compound 1 was elucidated by extensive nuclear magnetic resonance (NMR data (1H- and 13C-NMR, 1H-1H correlation spectroscopy (1H-1H COSY, heteronuclear single-quantum correlation (HSQC, heteronuclear multiple bond correlation (HMBC, and nuclear overhauser effect spectroscopy (NOESY and HR-FABMS analysis. The anti-inflammatory effects of 1–8 were evaluated in lipopolysaccharide (LPS-stimulated murine microglia BV-2 cells. Compounds 4 and 7 exhibited moderate inhibitory effects on nitric oxide production in LPS-activated BV-2 cells, with IC50 values of 17.80 and 27.91 µM, respectively.

  11. Bacteroides thetaiotaomicron VPI-5482 glycoside hydrolase family 66 homolog catalyzes dextranolytic and cyclization reactions.

    Science.gov (United States)

    Kim, Young-Min; Yamamoto, Eiji; Kang, Min-Sun; Nakai, Hiroyuki; Saburi, Wataru; Okuyama, Masayuki; Mori, Haruhide; Funane, Kazumi; Momma, Mitsuru; Fujimoto, Zui; Kobayashi, Mikihiko; Kim, Doman; Kimura, Atsuo

    2012-09-01

    Bacteroides thetaiotaomicron VPI-5482 harbors a gene encoding a putative cycloisomaltooligosaccharide glucanotransferase (BT3087) belonging to glycoside hydrolase family 66. The goal of the present study was to characterize the catalytic properties of this enzyme. Therefore, we expressed BT3087 (recombinant endo-dextranase from Bacteroides thetaiotaomicron VPI-5482) in Escherichia coli and determined that recombinant endo-dextranase from Bacteroides thetaiotaomicron VPI-5482 preferentially synthesized isomaltotetraose and isomaltooligosaccharides (degree of polymerization > 4) from dextran. The enzyme also generated large cyclic isomaltooligosaccharides early in the reaction. We conclude that members of the glycoside hydrolase 66 family may be classified into three types: (a) endo-dextranases, (b) dextranases possessing weak cycloisomaltooligosaccharide glucanotransferase activity, and (c) cycloisomaltooligosaccharide glucanotransferases. © 2012 The Authors Journal compilation © 2012 FEBS.

  12. NATURAL PLANT TOXICANT – CYANOGENIC GLYCOSIDE AMYGDALIN: CHARACTERISTIC, METABOLISM AND THE EFFECT ON ANIMAL REPRODUCTION

    Directory of Open Access Journals (Sweden)

    Eduard Kolesár

    2015-02-01

    Full Text Available The amount of cyanogenic glycosides, as natural plant toxicants, in plants varies with plant species and environmental effects. Cyanogenic glycoside as an amygdalin was detected in apricot kernels, bitter almonds and peach, plum, pear and apple seeds. Amygdalin itself is non-toxic, but its HCN production decomposed by some enzymes is toxic substance. Target of this review was to describe the characteristic, metabolism and possible effects of amygdalin on reproductive processes. Previous studies describe the effects of natural compound amygdalin on female and male reproductive systems focused on process of steroidogenesis, spermatozoa motility and morphological abnormalities of spermatozoa. In accordance to the previous studies on amygdalin its benefit is controversial.

  13. Unusual metal complex of cadinane sesquiterpene alkaloid and new neolignan glycosides from Alangium alpinum.

    Science.gov (United States)

    Ren, Jie; Xie, Yang-Guo; Guo, Yi-Gong; Zhu, Sheng-Lan; Jin, Hui-Zi; Zhang, Wei-Dong

    2018-03-01

    One unusual metal complex of cadinane sesquiterpene alkaloid (1), one new cadinane sesquiterpene alkaloid (2) and two new neolignan glycosides (3-4) along with six known cadinane sesquiterpene derivatives (5-10), nineteen known phenolic glycosides (11-29) were isolated from the aerial parts of Alangium alpinum. Structures of new crystals of metal complex were characterized by X-Ray diffraction and ICP-AES analysis. Other new compounds were elucidated by combined use and detailed analysis of HR-ESIMS, 1D and 2D NMR and CD spectroscopic method. In addition, all isolated compounds were tested for their inhibitory effects against TNF-α induced NF-κB activation in Hela cells and NO production in RAW 264.7 macrophages. Copyright © 2017 Elsevier B.V. All rights reserved.

  14. Flavonoid glycosides and alkaloids from the embryos of Nelumbo nucifera seeds and their antioxidant activity.

    Science.gov (United States)

    Jiang, Xi-Lan; Wang, Lun; Wang, En-Jun; Zhang, Guo-Lin; Chen, Bin; Wang, Ming-Kui; Li, Fu

    2018-03-01

    Chemical investigation of the embryos of Nelumbo nucifera afforded four new flavone C-glycosides, named nelumbosides A-D (1-4), together with nine known ones, comprising five flavonoids (5-9) and four alkaloids (10-13). The chemical structures of the new compounds were elucidated by 1D, 2D-NMR and HR-ESI-MS techniques, together with chemical methods. Nelumbosides A-D (1-4) are rarely present in naturally occurring flavone C-glycosides featuring a 4-hydroxystyrene unit connected to the flavonoid skeleton. Compounds 2-13 were evaluated for their antioxidant activity by ABTS and DPPH radical-scavenging assay. Among them, compounds 2, 6, 7 and 11 exhibited strong scavenging activity with SC 50 values ranging from 12.07 to 25.68μM compared with the positive control l-ascorbic acid. Copyright © 2018 Elsevier B.V. All rights reserved.

  15. Anti-allergic inflammatory effects of cyanogenic and phenolic glycosides from the seed of Prunus persica.

    Science.gov (United States)

    Kim, Geum Jin; Choi, Hyun Gyu; Kim, Ji Hyang; Kim, Sang Hyun; Kim, Jeong Ah; Lee, Seung Ho

    2013-12-01

    A methanol extract of the seed of Prunus persica (Rosaceae) was found to inhibit histamine release in human mast cells. Activity-guided fractionation of the methanol extract yielded three cyanogenic glycosides (1-3) and other phenolic compounds (4-8). To evaluate their anti-allergic and anti-inflammatory activities, the isolates (1-8) were tested for their inhibitory effects on histamine release and on the gene expressions of tumor necrosis factor (TNF)-alpha and interleukin (IL)-6 in human mast cells. Of these, phenolic glycosides 7 and 8 suppressed histamine release and inhibited the pro-inflammatory cytokines TNF-alpha and IL-6. These results suggest that isolates from P. persica are among the anti-allergic inflammatory principles in this medicinal plant.

  16. Synthesis and Characterization of Hapten-Protein Conjugates for Antibody Production against Cyanogenic Glycosides.

    Science.gov (United States)

    Bolarinwa, Islamiyat Folashade

    2015-07-01

    Consumption of cyanogenic plants can cause serious health problems for humans. The ability to detect and quantify cyanogenic glycosides, capable of generating cyanide, could contribute to prevention of cyanide poisoning from the consumption of improperly processed cyanogenic plants. Hapten-protein conjugates were synthesized with amygdalin and linamarin by using a novel approach. Polyclonal antibodies were generated by immunizing four New Zealand White rabbits with synthesized amygdalin-bovine serum albumin and linamarin-bovine serum albumin immunogen. This is the first time an antibody was produced against linamarin. Antibody titer curves were obtained from all the four rabbits by using a noncompetitive enzyme-linked immunosorbent assay. High antibody titer was obtained at dilutions greater than 1:50,000 from both immunogens. This new method is an important step forward in preventing ingestion of toxic cyanogenic glycosides.

  17. Mycotoxins and cyanogenic glycosides in staple foods of three indigenous people of the Colombian Amazon.

    Science.gov (United States)

    Diaz, Gonzalo J; Krska, Rudolf; Sulyok, Michael

    2015-01-01

    A study was conducted to determine the incidence and levels of mycotoxins in the main staple foods of three indigenous people of the Colombian Amazon. A total of 20 corn, 24 rice and 59 cassava samples were analysed by a multi-analyte liquid chromatography-tandem mass spectrometry method covering the major classes of mycotoxins. In addition, cassava samples were also analysed for cyanogenic glycosides. The indigenous Amazon communities tested are exposed to potentially carcinogenic mycotoxins (particularly aflatoxins), as well as other mycotoxins, mainly through the intake of locally grown corn. Citrinin content in this corn was unusually high and has not been reported elsewhere. Two cassava samples contained high levels of cyanogenic glycosides. It is strongly recommended not to grow corn in the Amazon but instead purchase it from vendors capable of guaranteeing mycotoxin levels below the maximum allowable concentration in Colombia.

  18. Effect of Blueberry Anthocyanins Malvidin and Glycosides on the Antioxidant Properties in Endothelial Cells.

    Science.gov (United States)

    Huang, Wuyang; Zhu, Yunming; Li, Chunyang; Sui, Zhongquan; Min, Weihong

    2016-01-01

    The objective of this research was to survey the antioxidant functional role of the main anthocyanins of blueberries in endothelial cells. Changes on the reactive oxygen species (ROS), xanthine oxidase-1 (XO-1), superoxide dismutase (SOD), and heme oxygenase-1 (HO-1) in cells of malvidin and the two glycosides were investigated. The results showed that these anthocyanins decreased the levels of ROS and XO-1 but increased the levels of SOD and HO-1. Glycosides improved the antioxidant capacity of malvidin to a great extent. The changes in the antioxidant properties of malvidin-3-glucoside were more pronounced than malvidin-3-galactoside. Variation in levels of malvidin-3-glucoside and malvidin-3-galactoside had a significant impact on antioxidant properties to different extents. It indicates that blueberries are a good resource of anthocyanins, which can protect cells from oxidative deterioration and use blueberry as a potential functional food to prevent diseases related to oxidative stress.

  19. Effect of Blueberry Anthocyanins Malvidin and Glycosides on the Antioxidant Properties in Endothelial Cells

    Directory of Open Access Journals (Sweden)

    Wuyang Huang

    2016-01-01

    Full Text Available The objective of this research was to survey the antioxidant functional role of the main anthocyanins of blueberries in endothelial cells. Changes on the reactive oxygen species (ROS, xanthine oxidase-1 (XO-1, superoxide dismutase (SOD, and heme oxygenase-1 (HO-1 in cells of malvidin and the two glycosides were investigated. The results showed that these anthocyanins decreased the levels of ROS and XO-1 but increased the levels of SOD and HO-1. Glycosides improved the antioxidant capacity of malvidin to a great extent. The changes in the antioxidant properties of malvidin-3-glucoside were more pronounced than malvidin-3-galactoside. Variation in levels of malvidin-3-glucoside and malvidin-3-galactoside had a significant impact on antioxidant properties to different extents. It indicates that blueberries are a good resource of anthocyanins, which can protect cells from oxidative deterioration and use blueberry as a potential functional food to prevent diseases related to oxidative stress.

  20. Family of Ricinus communis Monosaccharide Transporters and RcSTP1 in Promoting the Uptake of a Glucose-Fipronil Conjugate.

    Science.gov (United States)

    Mao, Gen-Lin; Yan, Yin; Chen, Yan; Wang, Bing-Feng; Xu, Fei-Fei; Zhang, Zhi-Xiang; Lin, Fei; Xu, Han-Hong

    2017-08-02

    Enhancing the systemic distribution of a bioactive compound by exploiting the vascular transport system of a plant presents a means of reducing both the volume and frequency of pesticide/fungicide application. The foliar uptake of the glucose-fipronil conjugate N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine (GTF) achieved in castor bean (Ricinus communis) and its transport via the phloem are known to be mediated by monosaccharide transporter(s) [MST(s)], although neither the identity of the key MST(s) involved nor the mechanistic basis of its movement have yet to be described. On the basis of homology with Arabidopsis thaliana sugar transporters, the castor bean genome was concluded to harbor 53 genes encoding a sugar transporter, falling into the eight previously defined subfamilies INT, PMT, VGT, STP, ERD6, pGlucT, TMT, and SUT. Transcriptional profiling identified the product of RcSTP1 as a candidate for mediating GTF uptake, because this gene was induced by exposure of the plant to GTF. When RcSTP1 was transiently expressed in onion epidermis cells, the site of RcSTP1 deposition was shown to be the plasma membrane. A functional analysis based on RcSTP1 expression in Xenopus laevis oocytes demonstrated that its product has a high affinity for GTF. The long-distance root-to-shoot transport of GTF was enhanced in a transgenic soybean chimera constitutively expressing RcSTP1.

  1. Evaluation of the Antihyperglycemic Effect of Minor Steviol Glycosides in Normoglycemic and Induced-Diabetic Wistar Rats.

    Science.gov (United States)

    Aranda-González, Irma; Moguel-Ordóñez, Yolanda; Chel-Guerrero, Luis; Segura-Campos, Maira; Betancur-Ancona, David

    2016-09-01

    Steviol glycosides are a family of compounds found in Stevia rebaudiana Bertoni that are responsible for sweetness capacity. The antihyperglycemic effect of the two major steviol glycosides, Rebaudioside A and Stevioside, has been studied and it has been found that despite having the same common structure, only Stevioside exerts an antihyperglycemic effect. Although other steviol derivatives are found in smaller amounts (minor steviol glycosides) in S. rebaudiana, whether or not they possess antihyperglycemic activity has not been evaluated. The aim of this study was to evaluate the antihyperglycemic effect of minor steviol glycosides in normoglycemic and diabetic (streptozotocin/nicotinamide) Wistar rats. Rats were subjected to an intraperitoneal glucose tolerance test (IPGTT) both before and after chronic treatment (28 days). After 6 h of fasting, IPGTT was conducted in pentobarbital-anesthetized rats using 1 g/kg of glucose plus 20 mg/kg of the minor glycoside (Dulcoside A, Rebaudioside B, C, D, or Steviolbioside) or control treatment (distilled water, glibenclamide, or metformin); the blood of the tip of the tail was collected at time 0, 15, 30, 60, and 120 min.; and blood glucose was measured, and its net area under the curve (AUCnet) was calculated. After 28-day chronic oral administration, IPGTT was again performed. Differences were considered significant at P diabetic Wistar rats. Considering the dose tested, it is unlikely that these glycosides have an effect on glucose in diabetic or normoglycemic humans.

  2. Induction of apoptosis in colon cancer cells treated with isorhamnetin glycosides from Opuntia ficus-indica pads.

    Science.gov (United States)

    Antunes-Ricardo, Marilena; Moreno-García, Beatriz E; Gutiérrez-Uribe, Janet A; Aráiz-Hernández, Diana; Alvarez, Mario M; Serna-Saldivar, Sergio O

    2014-12-01

    (OFI) contains health-promoting compounds like flavonoids, being the isorhamnetin glycosides the most abundant. We evaluated the effect of OFI extracts with different isorhamnetin glycosides against two different human colon cancer cells (HT-29 and Caco2). The extracts were obtained by alkaline hydrolysis with NaOH at 40 °C during 15, 30 or 60 min. Tri and diglycosides were the most abundant isorhamnetin glycosides, therefore these compounds were isolated to compare their cytotoxic effect with the obtained from the extracts. The OFI extracts and purified isorhamnetin glycosides were more cytotoxic against HT-29 cells than Caco2 cells. OFI-30 exhibited the lowest IC50 value against HT-29 (4.9 ± 0.5 μg/mL) and against Caco2 (8.2 ± 0.3 μg/mL). Isorhamnetin diglycosides IG5 and IG6 were more cytotoxic than pure isorhamnetin aglycone or triglycosides when they were tested in HT-29 cells. Bioluminescent analysis revealed increased activity of caspase 3/7 in OFI extracts-treated cells, particularly for the extract with the highest concentration of isorhamnetin triglycosides. Flow cytometry analysis confirmed that OFI extract and isorhamnetin glycosides induced a higher percentage of apoptosis in HT-29 than in Caco2, while isorhamnetin was more apoptotic in Caco2. This research demonstrated that glycosilation affected antiproliferative effect of pure isorhamnetin glycosides or when they are mixed with other phytochemicals in an extract obtained from OFI.

  3. Special Effect of Ionic Liquids on the Extraction of Flavonoid Glycosides from Chrysanthemum morifolium Ramat by Microwave Assistance

    Directory of Open Access Journals (Sweden)

    Ying Zhou

    2015-04-01

    Full Text Available A microwave-assisted extraction approach based on ionic liquids of different chain lengths was successfully applied to the extraction of ten flavonoid glycosides from the flowering heads of Chrysanthemum morifolium Ramat. The pretreated sample was quantified by HPLC-ESI-MSn. The main components were identified as flavonoid glycosides, including three luteolin glycosides, three apigenin glycosides, three kaempferide glycosides, and one acacetin glycoside according to the characteristics of the corresponding CID mass spectrometric patterns. Eight ionic liquids from the imidazolium family with different chain lengths, namely, 1-alkyl-3-methylimidazolium bromide, [Cnmim]Br, (n = 2–16 were studied as extraction medium in water. Results indicated that alkyl chain length had an irregular impact on the extraction efficiency. Moreover, the best extraction efficiency was achieved by 1-dodecyl-3-methylimidazolium bromide aqueous solution ([C12mim]Br. Besides the alkyl chain length of the cations, other factors influencing extraction efficiency were systematically investigated, including concentration of the IL solutions, extraction time, matrix-to-solvent ratio and irradiation power.

  4. Special Effect of Ionic Liquids on the Extraction of Flavonoid Glycosides from Chrysanthemum morifolium Ramat by Microwave Assistance.

    Science.gov (United States)

    Zhou, Ying; Wu, Datong; Cai, Pengfei; Cheng, Guifang; Huang, Chaobiao; Pan, Yuanjiang

    2015-04-28

    A microwave-assisted extraction approach based on ionic liquids of different chain lengths was successfully applied to the extraction of ten flavonoid glycosides from the flowering heads of Chrysanthemum morifolium Ramat. The pretreated sample was quantified by HPLC-ESI-MSn. The main components were identified as flavonoid glycosides, including three luteolin glycosides, three apigenin glycosides, three kaempferide glycosides, and one acacetin glycoside according to the characteristics of the corresponding CID mass spectrometric patterns. Eight ionic liquids from the imidazolium family with different chain lengths, namely, 1-alkyl-3-methylimidazolium bromide, [Cnmim]Br, (n=2-16) were studied as extraction medium in water. Results indicated that alkyl chain length had an irregular impact on the extraction efficiency. Moreover, the best extraction efficiency was achieved by 1-dodecyl-3-methylimidazolium bromide aqueous solution ([C12mim]Br). Besides the alkyl chain length of the cations, other factors influencing extraction efficiency were systematically investigated, including concentration of the IL solutions, extraction time, matrix-to-solvent ratio and irradiation power.

  5. Tareciliosides A--G: Cycloartane glycosides from leaves of Tarenna gracilipes (HAY.) OHWI.

    Science.gov (United States)

    Zhao, Zhimin; Matsunami, Katsuyoshi; Otsuka, Hideaki; Shinzato, Takakazu; Takeda, Yoshio

    2008-08-01

    From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Tarenna gracilipes, collected in Okinawa, seven new cycloartane glycosides, named tareciliosides A--G (4--10), were isolated together with three known compounds, D-mannitol (1), (R)-linalool 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (2), and mussaenoside (3). Their structures were elucidated through a combination of spectroscopic analyses.

  6. Stevia : A True Glycoside Used as a Sweetener and Not Affecting Behavior

    OpenAIRE

    Marie-Claire Cammaerts, Axel Dero, Roger Cammaerts

    2016-01-01

    Using ants as models, the glycoside rebaudioside A, a sweetener extracted from the plant Stevia rebaudiana and commercialized under the name ‘stevia’, was shown to have no effect on their food consumption, locomotion, precision of reaction, response to pheromones, brood caring, cognition, visual and olfactory conditioning and memory, although this sweetener slightly increased the ants audacity. However, when having the choice between stevia and saccharose, the ants somewhat preferred the latt...

  7. Positive effects of cyanogenic glycosides in food plants on larval development of the common blue butterfly.

    Science.gov (United States)

    Goverde, Marcel; Bazin, Alain; Kéry, Marc; Shykoff, Jacqui A; Erhardt, Andreas

    2008-09-01

    Cyanogenesis is a widespread chemical defence mechanism in plants against herbivory. However, some specialised herbivores overcome this protection by different behavioural or metabolic mechanisms. In the present study, we investigated the effect of presence or absence of cyanogenic glycosides in birdsfoot trefoil (Lotus corniculatus, Fabaceae) on oviposition behaviour, larval preference, larval development, adult weight and nectar preference of the common blue butterfly (Polyommatus icarus, Lycaenidae). For oviposition behaviour there was a female-specific reaction to cyanogenic glycoside content; i.e. some females preferred to oviposit on cyanogenic over acyanogenic plants, while other females behaved in the opposite way. Freshly hatched larvae did not discriminate between the two plant morphs. Since the two plant morphs differed not only in their content of cyanogenic glycoside, but also in N and water content, we expected these differences to affect larval growth. Contrary to our expectations, larvae feeding on cyanogenic plants showed a faster development and stronger weight gain than larvae feeding on acyanogenic plants. Furthermore, female genotype affected development time, larval and pupal weight of the common blue butterfly. However, most effects detected in the larval phase disappeared for adult weight, indicating compensatory feeding of larvae. Adult butterflies reared on the two cyanogenic glycoside plant morphs did not differ in their nectar preference. But a gender-specific effect was found, where females preferred amino acid-rich nectar while males did not discriminate between the two nectar mimics. The presented results indicate that larvae of the common blue butterfly can metabolise the surplus of N in cyanogenic plants for growth. Additionally, the female-specific behaviour to oviposit preferably on cyanogenic or acyanogenic plant morphs and the female-genotype-specific responses in life history traits indicate the genetic flexibility of this

  8. Correlation between Stucture and Taste of Steviol Glycosides: Some preliminary Results

    OpenAIRE

    Jooken, Etienne; Amery, Ruis; Monballiu, Annick; Meesschaert, Boudewijn

    2013-01-01

    Fifteen commercial samples of steviol glycosides were tasted by a panel, and arranged according to sweetness and bitterness. The samples were also analysed by HPLC. It appeared that sweet tasting samples contained mainly RebA (and no Ste), whereas the opposite was true for bitter samples. Further refinement about the contribution to the taste from the other compounds could be done by correlating the concentrations of these compounds to the sweetness or bitterness of the samp...

  9. Two new acylated flavonol glycosides from Mimosa pigra L. leaves sub-family Mimosoideae

    Directory of Open Access Journals (Sweden)

    Chinedu J. Okonkwo

    2016-12-01

    Conclusion: Myricetin, quercetin and their glycoside derivatives are strong antioxidants; and elicit cytotoxic effect on human cancer cell lines among other pharmacological activities. The isolation of acylated flavonoids in M. pigra provided an important insight on the evolutionary trend of the medicinal plant. While the dominance of flavonols, may account for the various ethnomedicinal uses of the herb and the mechanism and mode of its confirmed pharmacological actions.

  10. [Flavone C-glycosides from seeds of Ziziphus jujuba var. spinosa].

    Science.gov (United States)

    Chen, Ke-xian; Zhao, Li-mei; Ji, Chang-jiu; Tan, Ning-hua

    2015-04-01

    Five flavone C-glycosides were isolated from the methanol extract of the degrease seeds of Ziziphus jujuba var. spinosa though various column chromatography methods including silica gel, MPLC, and HPLC. The structures were elucidated as 6"-feruloyl- 6'''-vanillylspinosin(1), 6",6'"-diferuloylspinosin(2), spinosin(3), swertisin(4) and isoswertisin(5) based on the NMR and MS spectral data. 1 is a new compound.

  11. A new sesquiterpene lactone glycoside and a new quinic acid methyl ester from Patrinia villosa.

    Science.gov (United States)

    Yang, Yong-Fen; Ma, Hong-Mei; Chen, Gang; Wang, Hai-Feng; Xiang, Zheng; Feng, Qing-Mei; Hua, Hui-Ming; Pei, Yue-Hu

    2016-10-01

    A new sesquiterpene lactone glycoside (1) and a new quinic acid methyl ester (2) were isolated from Patrinia villosa, together with another two known compounds chlorogenic acid n-butyl ester (3), 3, 4-di-O-caffeoylquinic acid methyl ester (4). Their structures were established using 1D/2D-NMR spectroscopy, mass spectrometry, and comparing with spectroscopic data reported in the literature.

  12. Phytochemical studies for quantitative estimation of iridoid glycosides in Picrorhiza kurroa Royle

    OpenAIRE

    Sultan, Phalisteen; Jan, Arif; Pervaiz, Qazi

    2016-01-01

    Background Picrorhiza kurroa Royle commonly known as ?Kutki or Kutaki? is an important medicinal plant in Ayurvedic system of medicine and has traditionally been used to treat disorders of the liver and upper respiratory tract. The plant is the principle source of iridoid glycosides, picrosides I, II and kutkoside used in various herbal drug formulations mainly as strong hepatoprotective and immune-modulatory compound. The species has become endangered to near extinction due to the unregulate...

  13. New monocyclic monoterpenoid glycoside from Mentha haplocalyx Briq.

    OpenAIRE

    She Gai-Mei; Xu Chao; Liu Bin

    2012-01-01

    Abstract Two new monocyclic monoterpenoid glycosides, rel-(1R,2S,3R,4R) p-menthane-1,2,3-triol 3-O-β-D-glucopyranoside (1) and rel- (1S,2R,3S) terpinolene-1,2,3-triol 3-O-β-D-glucopyranoside (2) were isolated from aqueous acetone extract of the aerial parts of Mentha haplocalyx Briq.. Their structures were elucidated through spectral analysis using MS and NMR spectrometers.

  14. Nondestructive determination of lignans and lignan glycosides in sesame seeds by near infrared reflectance spectroscopy.

    Science.gov (United States)

    Kim, Kwan Su; Park, Si Hyung; Choung, Myoung Gun

    2006-06-28

    Sesame (Sesamum indicum L.) contains abundant lignans including lipid-soluble lignans (sesamin and sesamolin) and water-soluble lignan glycosides (sesaminol triglucoside and sesaminol diglucoside) related to antioxidative activity. In this study, near infrared reflectance spectroscopy (NIRS) was used to develop a rapid and nondestructive method for the determination of lignan contents on intact sesame seeds. Ninety-three intact seeds were scanned in the reflectance mode of a scanning monochromator. This scanning procedure did not require the pulverization of samples, allowing each analysis to be completed within minutes. Reference values for lignan contents were obtained by high-performance liquid chromatography analysis. Calibration equations for lignans (sesamin and sesamolin) and lignan glycosides (sesaminol triglucoside and sesaminol diglucoside) contents were developed using modified partial least squares regression with internal cross-validation (n = 63). The equations obtained had low standard errors of cross-validation and moderate R2 (coefficient of determination in calibration). The prediction of an external validation set (n = 30) showed significant correlation between reference values and NIRS predicted values based on the SEP (standard error of prediction), bias, and r2 (coefficient of determination in prediction). The models developed in this study had relatively higher values (more than 2.0) of SD/SEP(C) for all lignans and lignan glycosides except for sesaminol diglucoside, which had a minor amount, indicating good correlation between the reference and the NIRS estimate. The results showed that NIRS, a nondestructive screening method, could be used to rapidly determine lignan and lignan glycoside contents in the breeding programs for high quality sesame.

  15. Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades

    OpenAIRE

    Bahrami, Yadollah; Franco, Christopher M. M.

    2016-01-01

    Sea cucumbers have been valued for many centuries as a tonic and functional food, dietary delicacies and important ingredients of traditional medicine in many Asian countries. An assortment of bioactive compounds has been described in sea cucumbers. The most important and abundant secondary metabolites from sea cucumbers are triterpene glycosides (saponins). Due to the wide range of their potential biological activities, these natural compounds have gained attention and this has led to their ...

  16. Enzymes that cleave non-glycosidic ether bonds between lignins or derivatives thereof and saccharides

    Energy Technology Data Exchange (ETDEWEB)

    Kravit, Nancy G.; Schmidt, Katherine A.

    2017-10-24

    The patent application relates to isolated polypeptides that specifically cleave non-glycosidic ether bonds between lignins or derivatives thereof and saccharides, and to cDNAs encoding the polypeptides. The patent application also relates to nucleic acid constructs, expression vectors and host cells comprising the cDNAs, as well as methods of producing and using the isolated polypeptides for treating pulp and biomass to increase soluble saccharide yield and enrich lignin fractions.

  17. Enhancement of production of eugenol and its glycosides in transgenic aspen plants via genetic engineering.

    OpenAIRE

    KOEDUKA, Takao; Suzuki, Shiro; Iijima, Yoko; Ohnishi, Toshiyuki; Suzuki, Hideyuki; Watanabe, Bunta; Shibata, Daisuke; UMEZAWA, Toshiaki; Pichersky, Eran; Hiratake, Jun

    2013-01-01

    Eugenol, a volatile phenylpropene found in many plant species, exhibits antibacterial and acaricidal activities. This study attempted to modify the production of eugenol and its glycosides by introducing petunia coniferyl alcohol acetyltransferase (PhCFAT) and eugenol synthase (PhEGS) into hybrid aspen. Gas chromatography analyses revealed that wild-type hybrid aspen produced small amount of eugenol in leaves. The heterologous overexpression of PhCFAT alone resulted in up to 7-fold higher eug...

  18. A possible glycosidic benzophenone with full substitution on B-ring from Psidium guajava leaves.

    Science.gov (United States)

    Venditti, Alessandro; Ukwueze, Stanley E

    2017-04-01

    Bidimensional NMR analysis may be a useful tool to resolve the structure of chemical compounds also in mixture. This letter would demonstrate how these techniques could be applied e.g. to the reported case on identification of benzophenone glycoside from Psidium guajava. A tentative structure for the secondary component, not yet described, was possibly proposed on the basis of observation and critic review of available 1D and 2D NMR spectra.

  19. Polygonumnolides C1-C4; minor dianthrone glycosides from the roots of Polygonum multiflorum Thunb.

    Science.gov (United States)

    Yang, Jian-Bo; Li, Li; Dai, Zhong; Wu, Yu; Geng, Xing-Chao; Li, Bo; Ma, Shuang-Cheng; Wang, Ai-Guo; Su, Ya-Lun

    2016-09-01

    Four new dianthrone glycosides, named polygonumnolides C1-C4 (1-4), were isolated from the dried roots of Polygonum multiflorum Thunb, together with two known emodin dianthrones (5-6). Their hepatotoxicities were evaluated against L-02 cell lines. Compounds 1-4 showed weak hepatotoxicity against L-02 cell lines with IC50 values of 313.05, 205.20, 294.20, and 207.35 μM, respectively.

  20. Fatty Acid and Alkenil Glycoside from the Fruits of Mengkudu (Morinda citrifolia Linn

    Directory of Open Access Journals (Sweden)

    Ferlinahayati

    2016-06-01

    Full Text Available Two compounds were isolated from methanol extract of mengkudu fruit (Morinda.citrifolia Linn. The extraction was conducted by maceration, while separation and purification using several chromatographic techniques. The compound structures were determined by spectral data including IR, 1H-NMR and GC-MS. Compound 1 was a mixture of 7 fatty acids with hexadecanoic acid as a primarily, meanwhile compound 2 was a mixture of an alkenyl glycoside with an aromatic.

  1. Neo-clerodane diterpenoids and phenylethanoid glycosides from Teucrium chamaedrys L.

    Science.gov (United States)

    Bedir, Erdal; Manyam, Rangavalli; Khan, Ikhlas A

    2003-08-01

    A neo-clerodane type diterpenoid, 12(S)-15,16-epoxy-19-hydroxy-neo-cleroda-13(16),14-dien-18,6alpha:20,12-diolide, and two phenylethanoid glycosides, teucrioside-3(IIII)-O-methylether and teucrioside-3(IIII),4(IIII)-O-dimethylether were isolated from the aerial parts of Teucrium chamaedrys. Their structures were identified on the basis of extensive NMR spectra, LC-ESIMS analysis, and molecular modeling studies.

  2. Coping with toxic plant compounds--the insect's perspective on iridoid glycosides and cardenolides.

    Science.gov (United States)

    Dobler, Susanne; Petschenka, Georg; Pankoke, Helga

    2011-09-01

    Specializing on host plants with toxic secondary compounds enforces specific adaptation in insect herbivores. In this review, we focus on two compound classes, iridoid glycosides and cardenolides, which can be found in the food plants of a large number of insect species that display various degrees of adaptation to them. These secondary compounds have very different modes of action: Iridoid glycosides are usually activated in the gut of the herbivores by β-glucosidases that may either stem from the food plant or be present in the gut as standard digestive enzymes. Upon cleaving, the unstable aglycone is released that unspecifically acts by crosslinking proteins and inhibiting enzymes. Cardenolides, on the other hand, are highly specific inhibitors of an essential ion carrier, the sodium pump. In insects exposed to both kinds of toxins, carriers either enabling the safe storage of the compounds away from the activating enzymes or excluding the toxins from sensitive tissues, play an important role that deserves further analysis. To avoid toxicity of iridoid glycosides, repression of activating enzymes emerges as a possible alternative strategy. Cardenolides, on the other hand, may lose their toxicity if their target site is modified and this strategy has evolved multiple times independently in cardenolide-adapted insects. Copyright © 2011 Elsevier Ltd. All rights reserved.

  3. Production of cadiotonic glycosides in Digitalis purpurea using temporary immersion systems

    Directory of Open Access Journals (Sweden)

    Naivy Pérez-Alonso

    2005-01-01

    Full Text Available Digitalis purpurea, is an example of cardiotonic drug. Digoxin and digitoxin are glycosides produced by this plant which are cardiac stimulants with a wide use in the treatment of heart problems. The objective of this investigation was to study the effect of temporary immersion on biomass production and the content of cardiotonic glycosides (digitoxin and digoxin, determined by Liquid Cromatography. Biomass production was favoured by increasing the frequency of immersions. The highest value of fresh weight (106.2 g and lower porcentage of hyperhydricity (27 % were obtained with immersions of 2 minutes every 4 hours. The content of digoxin was always lower than digitoxin. However, the concentration of digoxin increases with 6 and 8 immersions per day, while the accumulation of digitoxin was stable in all treatments. The aeration rates did not increase the biomasss and the concentration of digoxine was nule, nevertheless the concentration of digitoxine increased up to 111μg g.DW. The effect of temporary immersion on glycosides accumulation in shoots of Digitalis purpurea presented in this paper has not been described in the literature till now. temporary immersion Keywords: digitoxin, digoxin, secondary metabolites,

  4. Oviposition stimulants for the monarch butterfly: flavonol glycosides from Asclepias curassavica.

    Science.gov (United States)

    Haribal, M; Renwick, J A

    1996-01-01

    The monarch butterfly, Danaus plexippus oviposits on milkweed plants, primarily within the Asclepiadaceae. Oviposition stimulants responsible for host plant recognition were isolated from Asclepias curassavica. Six flavonoid glycosides-quercetin 3-O-(2",6"-alpha-L-dirhamnopyranosyl)-beta-D-galactopyranoside, quercetin 3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-galactopyranoside, quercetin 3-O-(2"-O-alpha-L-rhamnopyranosyl)-beta-D-galactopyranoside, quercetin 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside, quercetin 3-O-beta-D-galactopyranoside, quercetin 3-O-beta-D-glucopyranoside, and an unidentified flavonoid mixture were isolated and characterized from this plant. An additional glycoside, possibly quercetin 3-O-(2",6"-alpha-L-dirhamnopyranosyl)-beta-D-glucopyranoside, which could not be separated from the first triglycoside, was also found in some batches of plant extract. The two dirhamnosyl glycosides, the glucosylgalactose and the rutinoside were found to be active as oviposition stimulants at 0.5 g leaf equivalents.

  5. Influence of Extraction Methods on the Yield of Steviol Glycosides and Antioxidants in Stevia rebaudiana Extracts.

    Science.gov (United States)

    Periche, Angela; Castelló, Maria Luisa; Heredia, Ana; Escriche, Isabel

    2015-06-01

    This study evaluated the application of ultrasound techniques and microwave energy, compared to conventional extraction methods (high temperatures at atmospheric pressure), for the solid-liquid extraction of steviol glycosides (sweeteners) and antioxidants (total phenols, flavonoids and antioxidant capacity) from dehydrated Stevia leaves. Different temperatures (from 50 to 100 °C), times (from 1 to 40 min) and microwave powers (1.98 and 3.30 W/g extract) were used. There was a great difference in the resulting yields according to the treatments applied. Steviol glycosides and antioxidants were negatively correlated; therefore, there is no single treatment suitable for obtaining the highest yield in both groups of compounds simultaneously. The greatest yield of steviol glycosides was obtained with microwave energy (3.30 W/g extract, 2 min), whereas, the conventional method (90 °C, 1 min) was the most suitable for antioxidant extraction. Consequently, the best process depends on the subsequent use (sweetener or antioxidant) of the aqueous extract of Stevia leaves.

  6. Human skeletal muscle digitalis glycoside receptors (Na,K-ATPase)--importance during digitalization.

    Science.gov (United States)

    Schmidt, T A; Holm-Nielsen, P; Kjeldsen, K

    1993-02-01

    The aims of the present study were to evaluate in humans the putative importance of skeletal muscle digitalis glycoside receptors (Na,K-ATPase) in the volume of distribution of digoxin and to assess whether therapeutic digoxin exposure might cause digitalis receptor upregulation in skeletal muscle. Samples of the vastus lateralis were obtained postmortem from 11 long-term (9 months to 9 years) digitalized (125-187.5 micrograms daily) and eight undigitalized subjects. In intact samples from digitalized patients, vanadate-facilitated 3H-ouabain binding increased 15% (p 0.30) before and after washing in specific digoxin antibody fragments, respectively. Thus, the present study indicates a approximately 13% occupancy of skeletal muscle digitalis glycoside receptors with digoxin during digitalization. In light of the large skeletal muscle contribution to body mass, this indicates that the skeletal muscle Na,K-ATPase pool constitutes a major volume of distribution for digoxin during digitalization. The results gave no indication of skeletal muscle digitalis glycoside receptor upregulation in response to digoxin treatment. On the contrary, there was evidence of significantly lower (37%, p digitalized patients, which may be of importance for skeletal muscle incapacity in heart failure.

  7. Profiling of iridoid glycosides in Vaccinium species by UHPLC-MS.

    Science.gov (United States)

    Heffels, Peter; Müller, Laura; Schieber, Andreas; Weber, Fabian

    2017-10-01

    The iridoid profile of four Vaccinium species was investigated using UHPLC-MS to obtain further information about this group of species for phytochemical characterization. Fruits of bog bilberry (Vaccinium uliginosum L.) showed 14 different iridoid glycosides with a total amount of 20mg/kg fresh weight (FW), whereas bilberry (Vaccinium myrtillus L.) contained 11 iridoid glycosides and a total amount of 127mg/kg FW. Highbush blueberry (Vaccinium corymbosum L.) and lowbush blueberry (Vaccinium angustifolium L.) contained none of the investigated iridoid glycosides. Among the different iridoids, the isomers scandoside and deacetylasperulosidic acid as well as a dihydro derivative thereof were described for the first time in the Ericaceae family. The p-coumaroyl isomers of scandoside, deacetylasperulosidic acid and dihydromonotropein are reported for the first time in V. myrtillus and V. uliginosum. Monotropein and its p-coumaroyl isomers were found for the first time in V. uliginosum. The comparison of iridoid profiles in bilberry fruit and juice samples revealed constant proportions throughout the juice processing. Quantification and profile determination of iridoids may be used for species differentiation and thus for authentication purposes. Copyright © 2016 Elsevier Ltd. All rights reserved.

  8. Antibacterial and antiparasitic activity of oleanolic acid and its glycosides isolated from marigold (Calendula officinalis).

    Science.gov (United States)

    Szakiel, Anna; Ruszkowski, Dariusz; Grudniak, Anna; Kurek, Anna; Wolska, Krystyna I; Doligalska, Maria; Janiszowska, Wirginia

    2008-11-01

    The antibacterial and antiparasitic activities of free oleanolic acid and its glucosides and glucuronides isolated from marigold (Calendula officinalis) were investigated. The MIC of oleanolic acid and the effect on bacterial growth were estimated by A600 measurements. Oleanolic acid's influence on bacterial survival and the ability to induce autolysis were measured by counting the number of cfu. Cell morphology and the presence of endospores were observed under electron and light microscopy, respectively. Oleanolic acid inhibited bacterial growth and survival, influenced cell morphology and enhanced the autolysis of Gram-positive bacteria suggesting that bacterial envelopes are the target of its activity. On the other hand, glycosides of oleanolic acid inhibited the development of L3 Heligmosomoides polygyrus larvae, the infective stage of this intestinal parasitic nematode. In addition, both oleanolic acid and its glycosides reduced the rate of L3 survival during prolonged storage, but only oleanolic acid glucuronides affected nematode infectivity. The presented results suggest that oleanolic acid and its glycosides can be considered as potential therapeutic agents.

  9. Mass Spectrometric Characterization of Benzoxazinoid Glycosides from Rhizopus-Elicited Wheat (Triticum aestivum) Seedlings.

    Science.gov (United States)

    de Bruijn, Wouter J C; Vincken, Jean-Paul; Duran, Katharina; Gruppen, Harry

    2016-08-17

    Benzoxazinoids function as defense compounds and have been suggested to possess health-promoting effects. In this work, the mass spectrometric behavior of benzoxazinoids from the classes benzoxazin-3-ones (with subclasses lactams, hydroxamic acids, and methyl derivatives) and benzoxazolinones was studied. Wheat seeds were germinated with simultaneous elicitation by Rhizopus. The seedling extract was screened for the presence of benzoxazinoid (glycosides) using reversed-phase ultra-high-performance liquid chromatography with photodiode array detection coupled in line to multiple-stage mass spectrometry (RP-UHPLC-PDA-MS(n)). Benzoxazin-3-ones from the different subclasses showed distinctly different ionization and fragmentation behaviors. These features were incorporated into a newly proposed decision guideline to aid the classification of benzoxazinoids. Glycosides of the methyl derivative 2-hydroxy-4-methoxy-1,4-benzoxazin-3-one were tentatively identified for the first time in wheat. We conclude that wheat seedlings germinated with simultaneous fungal elicitation contain a diverse array of benzoxazinoids, mainly constituted by benzoxazin-3-one glycosides.

  10. Characterization of steryl glycosides in marine microalgae by gas chromatography-triple quadrupole mass spectrometry (GC-QQQ-MS).

    Science.gov (United States)

    Yu, Shanshan; Zhang, Yufan; Ran, Yun; Lai, Wenyi; Ran, Zhaoshou; Xu, Jilin; Zhou, Chengxu; Yan, Xiaojun

    2018-03-01

    Steryl glycosides (SGs) are sterol conjugates found in various plants, especially in those making up human diets. It has been demonstrated that SGs have potential health benefits, and they could be used as food supplements in a variety of food matrixes. Marine microalgae are a potential resource for human food and ingredients. In this study, gas chromatography-triple quadrupole mass spectrometry (GC-QQQ-MS) was used to characterize unknown SGs in eight microalgae belonging to different classes (Isochrysis galbana 3011, Pavlova viridis, Platymonas helgolandica, Conticribra weissflogii, Thalassiosira pseudonana, Nitzschia closterium, Gymnodinium sp., and Karlodinum veneficum). The SGs were first extracted from lyophilized algae with chloroform-methanol, purified by solid-phase extraction and analyzed as trimethylsilyl derivatives. Nine SGs have been identified. In particular, new SGs like occelasteryl glycoside and stellasteryl glycoside were found in Gymnodinium sp., 24-methylene cholesteryl glycoside was detected in P. helgolandica, and 4,24-dimethylcholestan-3-yl glycoside was identified as the main constituent of microalga K. veneficum. The results also showed that the compositions of SGs in different microalgae varied, with a range of 5.234 to 0.036 g kg -1 , and microalga P. viridis contained the most abundant SGs. GC-QQQ-MS is a powerful tool to detect SGs with different structures from a variety of microalgae. The compositions of SGs in different microalgae varied greatly. Microalgae are a good source of highly valued SGs. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

  11. Crystal structure of glycoside hydrolase family 127 β-L-arabinofuranosidase from Bifidobacterium longum

    Energy Technology Data Exchange (ETDEWEB)

    Ito, Tasuku; Saikawa, Kyo [Department of Biotechnology, The University of Tokyo, Tokyo (Japan); Kim, Seonah [National Bioenergy Center, National Renewable Energy Laboratory, Golden, CO (United States); Fujita, Kiyotaka [Faculty of Agriculture, Kagoshima University, Korimoto, Kagoshima (Japan); Ishiwata, Akihiro [Synthetic Cellular Chemistry Laboratory, RIKEN (Japan); Kaeothip, Sophon [ERATO Glycotrilogy Project, JST, Wako, Saitama (Japan); Arakawa, Takatoshi; Wakagi, Takayoshi [Department of Biotechnology, The University of Tokyo, Tokyo (Japan); Beckham, Gregg T., E-mail: Gregg.Beckham@nrel.gov [National Bioenergy Center, National Renewable Energy Laboratory, Golden, CO (United States); Ito, Yukishige [Synthetic Cellular Chemistry Laboratory, RIKEN (Japan); ERATO Glycotrilogy Project, JST, Wako, Saitama (Japan); Fushinobu, Shinya, E-mail: asfushi@mail.ecc.u-tokyo.ac.jp [Department of Biotechnology, The University of Tokyo, Tokyo (Japan)

    2014-04-25

    Graphical abstract: - Highlights: • HypBA1 β-L-arabinofuranosidase belongs to glycoside hydrolase family 127. • Crystal structure of HypBA1 was determined. • HypBA1 consists of a catalytic barrel and two additional β-sandwich domains. • The active site contains a Zn{sup 2+} coordinated by glutamate and three cysteines. • A possible reaction mechanism involving cysteine as the nucleophile is proposed. - Abstract: Enzymes acting on β-linked arabinofuranosides have been unknown until recently, in spite of wide distribution of β-L-arabinofuranosyl oligosaccharides in plant cells. Recently, a β-L-arabinofuranosidase from the glycoside hydrolase family 127 (HypBA1) was discovered in the newly characterized degradation system of hydroxyproline-linked β-L-arabinooligosaccharides in the bacterium Bifidobacterium longum. Here, we report the crystal structure of HypBA1 in the ligand-free and β-L-arabinofuranose complex forms. The structure of HypBA1 consists of a catalytic barrel domain and two additional β-sandwich domains, with one β-sandwich domain involved in the formation of a dimer. Interestingly, there is an unprecedented metal-binding motif with Zn{sup 2+} coordinated by glutamate and three cysteines in the active site. The glutamate residue is located far from the anomeric carbon of the β-L-arabinofuranose ligand, but one cysteine residue is appropriately located for nucleophilic attack for glycosidic bond cleavage. The residues around the active site are highly conserved among GH127 members. Based on biochemical experiments and quantum mechanical calculations, a possible reaction mechanism involving cysteine as the nucleophile is proposed.

  12. Identification, quantification and antioxidant activity of acylated flavonol glycosides from sea buckthorn (Hippophae rhamnoides ssp. sinensis).

    Science.gov (United States)

    Chen, Chu; Xu, Xue-Min; Chen, Yang; Yu, Meng-Yao; Wen, Fei-Yan; Zhang, Hao

    2013-12-01

    A novel acylated flavonol glycoside: isorhamnetin (3-O-[(6-O-E-sinapoyl)-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside) (1), together with two known acylated flavonol glycosides: quercetin (3-O-[(6-O-E-sinapoyl)-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside) (2) and kaempferol (3-O-[(6-O-E-sinapoyl)-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside) (3) were isolated from the n-butanol fraction of sea buckthorn (Hippophae rhamnoides ssp. sinensis) berries for the first time by chromatographic methods, and their structures were elucidated using UV, MS, (1)H and (13)C NMR, and 2D NMR. Compounds 1-3 showed good scavenging activities, with respective IC50 values of 8.91, 4.26 and 30.90 μM toward the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical; respective Trolox equivalent antioxidant capacities of 2.89, 4.04 and 2.44 μM μM(-1) toward 2,2'-azino-bis-3-ethyl-benzothiazoline-6-sulphonate (ABTS) radical. The quantitative analysis of the isolated acylated flavonol glycosides was performed by HPLC-DAD method. The contents of compounds 1-3 were in the range of 12.2-31.4, 4.0-25.3, 7.5-59.7 mg/100 g dried berries and 9.1-34.5, 75.1-182.1, 29.2-113.4 mg/100 g dried leaves, respectively. Copyright © 2013. Published by Elsevier Ltd.

  13. Structural and functional analysis of a glycoside hydrolase family 97 enzyme from Bacteroides thetaiotaomicron.

    Science.gov (United States)

    Kitamura, Momoyo; Okuyama, Masayuki; Tanzawa, Fumiko; Mori, Haruhide; Kitago, Yu; Watanabe, Nobuhisa; Kimura, Atsuo; Tanaka, Isao; Yao, Min

    2008-12-26

    SusB, an 84-kDa alpha-glucoside hydrolase involved in the starch utilization system (sus) of Bacteroides thetaiotaomicron, belongs to glycoside hydrolase (GH) family 97. We have determined the enzymatic characteristics and the crystal structures in free and acarbose-bound form at 1.6A resolution. SusB hydrolyzes the alpha-glucosidic linkage, with inversion of anomeric configuration liberating the beta-anomer of glucose as the reaction product. The substrate specificity of SusB, hydrolyzing not only alpha-1,4-glucosidic linkages but also alpha-1,6-, alpha-1,3-, and alpha-1,2-glucosidic linkages, is clearly different from other well known glucoamylases belonging to GH15. The structure of SusB was solved by the single-wavelength anomalous diffraction method with sulfur atoms as anomalous scatterers using an in-house x-ray source. SusB includes three domains as follows: the N-terminal, catalytic, and C-terminal domains. The structure of the SusB-acarbose complex shows a constellation of carboxyl groups at the catalytic center; Glu532 is positioned to provide protonic assistance to leaving group departure, with Glu439 and Glu508 both positioned to provide base-catalyzed assistance for inverting nucleophilic attack by water. A structural comparison with other glycoside hydrolases revealed significant similarity between the catalytic domain of SusB and those of alpha-retaining glycoside hydrolases belonging to GH27, -36, and -31 despite the differences in catalytic mechanism. SusB and the other retaining enzymes appear to have diverged from a common ancestor and individually acquired the functional carboxyl groups during the process of evolution. Furthermore, sequence comparison of the active site based on the structure of SusB indicated that GH97 included both retaining and inverting enzymes.

  14. Lignans and aromatic glycosides from Piper wallichii and their antithrombotic activities.

    Science.gov (United States)

    Shi, Yan-Ni; Shi, Yi-Ming; Yang, Lian; Li, Xing-Cong; Zhao, Jin-Hua; Qu, Yan; Zhu, Hong-Tao; Wang, Dong; Cheng, Rong-Rong; Yang, Chong-Ren; Xu, Min; Zhang, Ying-Jun

    2015-03-13

    Piper wallichii (Miq.) Hand.-Mazz. is a medicinal plant used widely for the treatment of rheumatoid arthritis, inflammatory diseases, cerebral infarction and angina in China. Previous study showed that lignans and neolignans from Piper spp. had potential inhibitory activities on platelet aggregation. In the present study, we investigated the chemical constituents of Piper wallichii and their antithrombotic activities, to support its traditional uses. The methanolic extract of the air-dried stems of Piper wallichii was separated and purified using various chromatographic methods, including semi-preparative HPLC. The chemical structures of the isolates were determined by detailed spectroscopic analysis, and acidic hydrolysis in case of the new glycoside 2. Determination of absolute configurations of the new compound 1 was facilitated by calculated electronic circular dichroism using time-dependent density-functional theory. All compounds were tested for their inhibitory effects on platelet aggregation induced by platelet activating factor (PAF) in rabbits׳ blood model, from which the active ones were further evaluated the in vivo antithrombotic activity in zebrafish model. A new neolignan, piperwalliol A (1), and four new aromatic glycosides, piperwalliosides A-D (2-5) were isolated from the stems of Piper wallichii, along with 25 known compounds, including 13 lignans, six aromatic glycosides, two phenylpropyl aldehydes, and four biphenyls. Five known compounds (6-10) showed in vitro antiplatelet aggregation activities. Among them, (-)-syringaresinol (6) was the most active compound with an IC50 value of 0.52 mM. It is noted that in zebrafish model, the known lignan 6 showed good in vivo antithrombotic effect with a value of 37% at a concentration of 30 μM, compared with the positive control aspirin with the inhibitory value of 74% at a concentration of 125μM. This study demonstrated that lignans, phenylpropanoid and biphenyl found in Piper wallichii may be

  15. Green extraction of glycosides from Stevia rebaudiana (Bert. with low solvent consumption: A desirability approach

    Directory of Open Access Journals (Sweden)

    Paula M. Martins

    2016-12-01

    Full Text Available The sweet flavor of Stevia rebaudiana (Bert. leaf extract is well known and has raised the interest of huge food companies due to its natural bid. The extraction of their main glycosides stevioside and rebaudioside A is an important step on the preparation of final Stevia granules. The aim of the work reported here was to study and optimize the dynamic maceration of Stevia leaves using water and ethanol as green solvents. For instance, a fractional factorial design was chosen to evaluate the individual effects of the drug powder size, weight ratio of drug to solvent, temperature, agitation, and time on the yield of these glycosides. The glycosides were quantified by high pressure liquid chromatography. An exhaustive extraction by successive maceration steps showed that ethanol 70% was superior to water and ethanol 90% for stevioside and rebaudioside extraction. The liquid extract composition in dry basis and the yield of stevioside and rebaudioside A were significantly affected by the drug to solvent weight ratio, showing that larger volumes of solvent should be used. Furthermore, increasing solvent volume favors the extraction of the stevioside by a twofold factor as compared to rebaudioside A. Among the other factors, only drug powder size affected the yield of rebaudioside A significantly. The optimal solution for S. rebaudiana leaves dynamic extraction estimated by desirability functions methodology led to a condition which allows obtaining extraction yields of 2.31 and 1.24% for stevioside and rebaudioside A and their concentrations in dried extract corresponding to 8.38 and 4.51%, respectively. These high yields were obtained with drug to solvent ratio (1:10, w/w much higher than previous works, thus resulting in a more sustainable and green process.

  16. α-Amylase: an enzyme specificity found in various families of glycoside hydrolases

    DEFF Research Database (Denmark)

    Janeček, Štefan; Svensson, Birte; MacGregor, E. Ann

    2014-01-01

    of all carbohydrate-active enzymes, it is one of the most frequently occurring glycoside hydrolases (GH). α-Amylase is the main representative of family GH13, but it is probably also present in the families GH57 and GH119, and possibly even in GH126. Family GH13, known generally as the main α...... five CSRs and catalytic machinery, and adopt a (β/α)7-barrel fold. These family GH57 attributes are likely to be characteristic of α-amylases from the family GH119, too. With regard to family GH126, confirmation of the unambiguous presence of the α-amylase specificity may need more biochemical...

  17. A new sesquiterpene lactone and a new aromatic glycoside from Illicium difengpi

    Directory of Open Access Journals (Sweden)

    Lei Fang

    2011-10-01

    Full Text Available A new sesquiterpene lactone (1 and a new aromatic glycoside (2, together with three known compounds (3–5 were isolated from the stem bark of Illicium difengpi K. I. B et K. I. M. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRESIMS, and chemical methods. The absolute configuration of the secondary alcohol in 1 was confirmed by Mosher's method. Compound 2 exhibited significant anti-inflammatory activity with IC50 value of 6.72 μmol/L.

  18. Alkyl-imidazolium glycosides: non-ionic-cationic hybrid surfactants from renewable resources.

    Science.gov (United States)

    Salman, Abbas Abdulameer; Tabandeh, Mojtaba; Heidelberg, Thorsten; Hussen, Rusnah Syahila Duali; Ali, Hapipah Mohd

    2015-08-14

    A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures. Copyright © 2015 Elsevier Ltd. All rights reserved.

  19. Polyflavanostilbene A, a new flavanol-fused stilbene glycoside from Polygonum cuspidatum.

    Science.gov (United States)

    Li, Fushuang; Zhan, Zhilai; Liu, Fu; Yang, Yanan; Li, Li; Feng, Ziming; Jiang, Jianshuang; Zhang, Peicheng

    2013-02-01

    Polyflavanostilbene A, a new flavanol-fused stilbene glycoside, was isolated from the rhizome of Polygonum cuspidatum. Its unusual structure, including its absolute stereochemistry, was determined by UV, IR, HRESIMS, and 1D and 2D NMR data and by the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Polyflavanostilbene A has an unprecedented rearranged flavanol skeleton fused to stilbene via a hexahydrocyclopenta[c]furan moiety. Polyflavanostilbene A showed strong inhibitory activity against α-glucosidase with an IC(50) value of 17.7 μM.

  20. Flavonoid Glycosides and Other Hydrophilic Compounds from Flowers of Heterotheca inuloides.

    Science.gov (United States)

    Jerga, C; Merfort, I; Willuhn, G

    1990-08-01

    Ten flavonoid glycosides were identified in flowers of HETEROTHECA INULOIDES ("Mexican Arnica"). Their structures were established by spectral data (UV, (1)H-NMR, (13)C-NMR, mass) and total acid hydrolysis as kaempferol 3-beta-glucoside, 3-beta-galactoside, 3-beta-rutinoside, 3-beta-robinobioside, quercetin 3-beta-glucoside, 3-beta-galactoside, 3-beta-glucuronide, 3-beta-glucuronide-6''-methylester, 3-alpha- L-arabinoside, and 3-beta-rutinoside. Additionally, caffeic, protocatechuic, and chlorogenic acid as well as umbelliferone were found.

  1. Effect of Morinda citrifolia fruit extract and its iridoid glycosides on blood fluidity.

    Science.gov (United States)

    Murata, Kazuya; Abe, Yumi; Futamura-Masuda, Megumi; Uwaya, Akemi; Isami, Fumiyuki; Deng, Shixin; Matsuda, Hideaki

    2014-07-01

    The aim of this study was to investigate the effect of Morinda citrifolia fruit on blood fluidity. M. citrifolia fruit extract (MCF-ext) was investigated for its influence on blood aggregation and fibrinolysis. MCF-ext inhibited polybrene-induced erythrocyte aggregation and thrombin activity. The fibrinolytic activity of MCF-ext, in the euglobulin lysis time test and fibrin plate assay, is reported here for the first time. One of the active compounds was an iridoid glycoside, asperulosidic acid. The results indicated that MCF-ext is a potentially useful health food which is capable of improving blood flow and preventing lifestyle-related diseases.

  2. Three new resin glycosides compounds from Argyreia acuta and their α-glucosidase inhibitory activity.

    Science.gov (United States)

    Wang, Li; Yan, You-Shao; Cui, Hong-Hua; Yin, Yong-Qin; Pan, Jie-Tao; Yu, Bang-Wei

    2017-03-01

    Three new phenolic compounds, acutacoside C (1), acutacoside D (2) and acutacoside E (3) were isolated from the aerial part of Argyreia acuta. The oligosaccharide chain was composed of two glucoses and three rhamnoses, and the aglycone was (11S)-hydroxyhexadecanoic acid (jalapinolic acid). The core of the three compounds was operculinic acid B, which was rare in resin glycosides. Their structures were established by a combination of spectroscopic and chemical methods. Compounds 1-3 have been evaluated for inhibitory activity against α-glucosidase, which all showed weak inhibitory activities.

  3. Two new steroidal glycosides isolated from the aerial part of Solanum torvum Swartz.

    Science.gov (United States)

    Shu, Weihu; Wu, Chun; Zhang, Ying; Ye, Wen-Cai; Zhou, Guangxiong

    2013-01-01

    One novel C-22 steroidal lactone saponin, namely solanolactoside C (1), and one new spirostanol glycoside, namely torvoside Q (2), were isolated from the ethanolic extract of aerial parts of Solanum torvum Swartz. The structures of 1 and 2 were determined by extensive NMR experiments including (1)H NMR, (13)C NMR, DEPT, (1)H-(1)H COSY, HSQC, HMBC and ROESY and HRESIMS to be solanolide 6-O-β-d-quinovopyranoside and neochlorogenin 6-O-[β-d-xylopyranosyl-(1 → 3)-β-d-glucopyranoside], respectively.

  4. Biomolecular proteomics discloses ATP synthase as the main target of the natural glycoside deglucoruscin.

    Science.gov (United States)

    Del Gaudio, Federica; Festa, Carmen; Mozzicafreddo, Matteo; Vasaturo, Michele; Casapullo, Agostino; De Marino, Simona; Riccio, Raffaele; Monti, Maria Chiara

    2016-10-20

    Extracts of Ruscus aculeatus are a rich source of bioactive steroidal glycosides, such as ruscogenins which are reported to act against chronic venous disorders. Nowadays, several preparations of its roots, commonly used in traditional medicine, are on the market as food supplements for health care and maintenance. Although spirostanol deglucoruscin is one of the main metabolites in these extracts, literature reports about its pharmacological profile are scarce. In this paper, a multi-disciplinary approach, based on chemical proteomics, molecular modelling and bio-organic assays, has been used to disclose the whole interactome of deglucoruscin and the F0-F1 ATP synthase complex has been found as its main target.

  5. Biosynthesis of coumarin glycosides by transgenic hairy roots of Polygonum multiflorum.

    Science.gov (United States)

    Zhou, Liangbin; Tian, Tian; Xue, Bailin; Song, Liyan; Liu, Ling; Yu, Rongmin

    2012-01-01

    To investigate the substrate specificity and regio-selectivity of coumarin glycosyltransferases in transgenic hairy roots of Polygonum multiflorum, esculetin (1) and eight hydroxycoumarins (2-9) were employed as substrates. Nine corresponding glycosides (10-18) involving four new compounds, 6-chloro-4-methylcoumarin 7-O-β-D-glucopyranoside (15), 6-chloro-4-phenylcoumarin 7-O-β-D-glucopyranoside (16), 8-hydroxy-4-methylcoumarin 7-O-β-D-glucopyranoside (17), and 8-allyl-4-methylcoumarin 7-O-β-D-glucopyranoside (18), were biosynthesized by the hairy roots.

  6. Acyl glycosides lignans, coumarins, and terpenes from the stems of Erycibe obtusifolia.

    Science.gov (United States)

    Liu, Zhao-Zhen; Zhan, Zhi-Lai; Liu, Fu; Yang, Ya-Nan; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2013-05-03

    Nine new acyl glycosides, obtusifosides A-I (1-9), and eight known compounds have been isolated from an EtOH extract of the stems of Erycibe obtusifolia. Their structures were elucidated on the basis of a spectroscopic data analysis (NMR, HRESIMS, and CD) and chemical evidence. The hepatoprotective effects of some of the compounds from d-galactosamine-induced cytotoxicity in HL-7702 hepatic cells were evaluated. Compounds 1, 10, 11, 13, 16, and 17 showed significant hepatoprotective activities compared with the positive control bicyclol at concentrations of 1×10(-5)M. Copyright © 2013 Elsevier Ltd. All rights reserved.

  7. A novel sulphur glycoside from the seeds of Descurainia sophia (L.).

    Science.gov (United States)

    Sun, K; Li, X; Liu, J-M; Wang, J-H; Li, W; Sha, Y

    2005-12-01

    A new sulphur glycoside, named descurainoside (1), and the known compound sinapic acid (2) have been isolated from the seeds of Descurainia sophia (L.) Webb ex Prantl. The structure of 1 has been identified as (1R,6S,8R,9S,10S)-9,10-dihydroxy-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-8-(hydroxymethyl)-2,7-dioxa-5-thiabicyclo[4.4.0]decan-3-one by means of physico-chemical properties and spectroscopic methods (1D and 2D NMR, HRMS, ESI-MS).

  8. Two Cytotoxic Coumarin Glycosides from the Aerial Parts of Diceratella elliptica (DC. Jonsell Growing in Egypt

    Directory of Open Access Journals (Sweden)

    Mona M. Marzouk

    2012-03-01

    Full Text Available Two new coumarin glycosides, 6-methoxy-5,7-dihydroxy-3,4-dihydrocoumarin-8-C-glucopyranoside (1 and 5-vinyl-6,7-dimethoxy-3,4-dihydrocoumarin-8-C-glucopyranoside (2, along with four known flavonoid compounds, were isolated from the aerial parts of Diceratella elliptica (DC. Jonsell growing in Egypt. Their structures were established on the basis of detailed chromatographic and spectroscopic techniques (UV, 1D NMR, 2D NMR, and ESIMS. Compounds 1 and 2 were evaluated for their cytotoxic activity and showed relatively high activity against three human carcinoma cell lines; liver (HEPG2, cervix (HELA and colon (HCT116.

  9. Phytochemical study of the trunk bark of Citharexylum spinosum L. growing in Tunisia: Isolation and structure elucidation of iridoid glycosides.

    Science.gov (United States)

    Saidi, Ilyes; Waffo-Téguo, Pierre; Ayeb-Zakhama, Asma E L; Harzallah-Skhiri, Fethia; Marchal, Axel; Ben Jannet, Hichem

    2018-02-01

    A phytochemical investigation of the trunk bark ethyl acetate extract of Citharexylum spinosum L. has led to the isolation of four previously undescribed iridoid glycosides, tunispinosides A-D, and five known phenylethanoid glycosides, verbascoside, leucosceptoside A, martynoside, isoverbascoside and plantainoside C, together with 4-hydroxy-2,6-dimethoxyphenyl 6'-O-vanilloyl-β-D-glucopyranoside, two 8,3'-neolignan glycosides, plucheosides D 1 -D 2 , coniferyl aldehyde, vanillic acid, syringic acid, ferulic acid and tyrosol. All compounds were isolated for the first time from C. spinosum. Their isolation was carried out using silica gel column and high performance liquid chromatography (HPLC). Structures were established by spectroscopic means including 1D and 2D NMR experiments, and spectrometric ESI-HRMS analysis. Copyright © 2017 Elsevier Ltd. All rights reserved.

  10. Terpene Glycosides from the Roots of Sanguisorba officinalis L. and Their Hemostatic Activities

    Directory of Open Access Journals (Sweden)

    Wei Sun

    2012-06-01

    Full Text Available Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-l-arabinofuranosyl-(1→6-β-d-glucopyranoside (1, geraniol-1-O-α-l-arabinofuranosyl-(1→6-β-d-glucopyranoside (2, geraniol-1-O-α-l-arabinopyranosyl-(1→6-β-d-glucopyranoside (3, 3β-[(α-l-arabinopyranosyloxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (4, 3β-[(α-l-arabinopyranosyl-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (ziyu-glycoside I, 5, 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-d-glucopyranoside (6 and 3β,19α-di-hydroxyurs-12-en-28-oic acid 28-β-d-glucopyranoside (7. Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 17 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5 showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.

  11. Sugar exchanges in arbuscular mycorrhiza: RiMST5 and RiMST6, two novel Rhizophagus irregularis monosaccharide transporters, are involved in both sugar uptake from the soil and from the plant partner.

    Science.gov (United States)

    Ait Lahmidi, Nassima; Courty, Pierre-Emmanuel; Brulé, Daphnée; Chatagnier, Odile; Arnould, Christine; Doidy, Joan; Berta, Graziella; Lingua, Guido; Wipf, Daniel; Bonneau, Laurent

    2016-10-01

    Arbuscular mycorrhizal (AM) fungi are associated with about 80% of land plants. AM fungi provide inorganic nutrients to plants and in return up to 20% of the plant-fixed CO2 is transferred to the fungal symbionts. Since AM fungi are obligate biotrophs, unraveling how sugars are provided to the fungus partner is a key for understanding the functioning of the symbiosis. In this study, we identified two new monosaccharide transporters from Rhizophagus irregularis (RiMST5 and RiMST6) that we characterized as functional high affinity monosaccharide transporters. RiMST6 was characterized as a glucose specific, high affinity H(+) co-transporter. We provide experimental support for a primary role of both RiMST5 and RiMST6 in sugar uptake directly from the soil. The expression patterns of RiMSTs in response to partial light deprivation and to interaction with different host plants were investigated. Expression of genes coding for RiMSTs was transiently enhanced after 48 h of shading and was unambiguously dependent on the host plant species. These results cast doubt on the 'fair trade' principle under carbon-limiting conditions. Therefore, in light of these findings, the possible mechanisms involved in the modulation between mutualism and parasitism in plant-AM fungus interactions are discussed. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  12. Identification of flavonoid glycosides in Rosa chinensis flowers by liquid chromatography-tandem mass spectrometry in combination with ¹³C nuclear magnetic resonance.

    Science.gov (United States)

    Qing, Lin-Sen; Xue, Ying; Zhang, Jian-Guang; Zhang, Zhi-Feng; Liang, Jian; Jiang, Yan; Liu, Yi-Ming; Liao, Xun

    2012-08-03

    Flowers of Rosa chinensis are widely used in traditional Chinese medicine as well as in food industry. Flavonoid glycosides are believed to be the major components in R. chinensis that are responsible for its antioxidant activities. In this work, a liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed for analysis of flavonoid glycosides presented in ethyl acetate extract of dried R. chinensis flowers. Twelve flavonoid glycosides were separated and detected. By comparing the retention times, UV spectra, and tandem MS fragments with those of respective authentic compounds, eight flavonoid glycosides were unequivocally identified. Although the other four were also identified as flavonoid glycosides, the glycosylation positions could not be determined due to lack of authentic compounds. Fortunately, the glycosylation effects were clearly observed in the (13)C NMR spectrum of the extract. The detailed structural information was, therefore, obtained to identify the four flavonoid glycosides as quercetin-3-O-D-glucoside, quercetin-3-O-D-xyloside, kaempferol-3-O-D-xyloside and quercetin-3-O-D-(6″-coumaroyl)-galactoside. These flavonoid glycosides were detected and identified for the first time in this botanic material. This work reports on the first use of (13)C NMR of a mixture to enhance a rapid HPLC-MS/MS analysis. The proposed analytical protocol was validated with a mixture of authentic flavonoid glycosides. Copyright © 2012 Elsevier B.V. All rights reserved.

  13. Effect of harvest timing on leaf production and yield of diterpene glycosides in Stevia rebaudiana Bert: a specialty perennial crop for Mississippi

    Science.gov (United States)

    Stevia rebaundiana (Bertoni), a perennial shrub of the Asteraceae, is one of the most important sources of non-caloric natural sweeteners. Stevia’s plant extracts and glycosides have been used for several years in Paraguay and Brazil. Several studies suggest that Stevia and its glycosides exert ben...

  14. Cardenolide glycosides of Thevetia peruviana and triterpenoid saponins of Sapindus emarginatus as TRAIL resistance-overcoming compounds.

    Science.gov (United States)

    Miyagawa, Takashi; Ohtsuki, Takashi; Koyano, Takashi; Kowithayakorn, Thaworn; Ishibashi, Masami

    2009-08-01

    A screening study for TRAIL resistance-overcoming activity was carried out, and activity-guided fractionations of Thevetia peruviana and Sapindus emarginatus led to the isolation of four cardenolide glycosides (1-4) and four triterpenoid saponins (5-8), respectively. In particular, cardenolide glycosides (1 and 2) from T. peruviana were shown to have a significant reversal effect on TRAIL resistance in human gastric adenocarcinoma cells, and real-time PCR showed that thevefolin (2) enhanced mRNA expression of death receptor 4 (DR4) and DR5. In addition, 1H and 13C NMR characterizations are shown for thevefolin (2) for the first time.

  15. Microbiological exploitation of cardiac glycosides and alkaloids from Garcinia kola, Borreria ocymoides, Kola nitida and Citrus aurantifolia.

    Science.gov (United States)

    Ebana, R U; Madunagu, B E; Ekpe, E D; Otung, I N

    1991-11-01

    The four medicinal plants, Garcinia kola (roots), Borreria ocymoides (leaves), Kola nitida (bark) and Citrus aurantifolia (roots) were screened for phytochemical components. They were found to contain tannins, phlobatannins, polyphenols, hydroxymethyl anthraquinones, glucides, saponins, alkaloids, cardiac glycosides, flavanoids and reducing compounds. The aqueous and alcoholic extracts as well as alkaloids and cardiac glycosides of the medicinal plants were tested on various pathogenic bacteria. They were found to inhibit such organisms as Staphylococcus aureus, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, beta-haemolytic streptococci, Escherichia coli and Neisseria gonorrhoeae. The usefulness of the phytochemical bases of these plants as potential sources of pharmaceutical drug preparation is discussed.

  16. [Effect of triterpene glycosides on the plasma membrane permeability for amino acids in Saccharomyces carlsbergensis yeast cells].

    Science.gov (United States)

    Anisimov, M M; Shcheglov, V V; Kiseleva, M I

    1978-01-01

    The effect of triterpen glycosides, such as cauloside C from Caulophyllum robustum, stichoposide A from Stichopus japonicus S and the asaponine from Thea sinensis L on permeability of the plasmic membranes for amino acids was studied. It was shown that the glycosides induced higher levels of liberation of the amino acids with positively or negatively charged molecules from the cells of Saccharomyces carlsbergensis as compared to the control. The transport of the non-polar amino acids was least affected by addition of the saponines to the incubation medium.

  17. Ability of human oral microbiota to produce wine odorant aglycones from odourless grape glycosidic aroma precursors.

    Science.gov (United States)

    Muñoz-González, Carolina; Cueva, Carolina; Ángeles Pozo-Bayón, M; Victoria Moreno-Arribas, M

    2015-11-15

    Grape aroma precursors are odourless glycosides that represent a natural reservoir of potential active odorant molecules in wines. Since the first step of wine consumption starts in the oral cavity, the processing of these compounds in the mouth could be an important factor in influencing aroma perception. Therefore, the objective of this work has been to evaluate the ability of human oral microbiota to produce wine odorant aglycones from odourless grape glycosidic aroma precursors previously isolated from white grapes. To do so, two methodological approaches involving the use of typical oral bacteria or the whole oral microbiota isolated from human saliva were followed. Odorant aglycones released in the culture mediums were isolated and analysed by HS-SPME-GC/MS. Results showed the ability of oral bacteria to hydrolyse grape aroma precursors, releasing different types of odorant molecules (terpenes, benzenic compounds and lipid derivatives). The hydrolytic activity seemed to be bacteria-dependent and was subject to large inter-individual variability. Copyright © 2015 Elsevier Ltd. All rights reserved.

  18. Development of a High Throughput Platform for Screening Glycoside Hydrolases based on Oxime-NIMS

    Directory of Open Access Journals (Sweden)

    Kai eDeng

    2015-10-01

    Full Text Available Cost effective hydrolysis of biomass into sugars for biofuel production requires high-performance low-cost glycoside hydrolase (GH cocktails that are active under demanding process conditions. Improving the performance of GH cocktails depends knowledge of many critical parameters including individual enzyme stabilities, optimal reaction conditions, kinetics and specificity of reaction. With this information, rate- and/or yield-limiting reactions that can be potentially improved through substitution, synergistic complementation, or protein engineering. Given the wide range of substrates and methods used for GH characterization, it is difficult to compare results across a myriad of approaches to identify high performance and synergistic combinations of enzymes. Here we describe a platform for systematic screening of GH activities using automatic biomass handling, bioconjugate chemistry, robotic liquid handling, and nanostructure-initiator mass spectrometry (NIMS. Twelve well-characterized substrates spanning the types of glycosidic linkages found in plant cell walls are included in the experimental workflow. To test the application of this platform and substrate panel, we studied the reactivity of three engineered cellulases and their synergy of combination across a range of reaction conditions and enzyme concentrations. We anticipate that large-scale screening using the standardized platform and substrates will generate critical datasets to enable direct comparison of enzyme activities for cocktail design.

  19. Reversal of multidrug resistance by morning glory resin glycosides in human breast cancer cells.

    Science.gov (United States)

    Figueroa-González, Gabriela; Jacobo-Herrera, Nadia; Zentella-Dehesa, Alejandro; Pereda-Miranda, Rogelio

    2012-01-27

    Reversal of multidrug resistance (MDR) by thirty resin glycosides from the morning glory family (Convolvulaceae) was evaluated in vinblastine-resistant human breast carcinoma cells (MCF-7/Vin). The effects of these amphipathic compounds on the cytotoxicity and P-glycoprotein (P-gp)-mediated MDR were estimated with the sulforhodamine B colorimetric assay. Active noncytotoxic compounds exerted a potentiation effect of vinblastine susceptibility by 1- to over 1906-fold at tested concentrations of 5 and 25 μg/mL. Murucoidin V (1) enhanced vinblastine activity 255-fold when incorporated at 25 μg/mL and also, based on flow cytometry, significantly increased the intracellular accumulation of rhodamine 123 with the use of reserpine as a positive control for a MDR reversal agent. Incubation of MCF-7/Vin cells with 1 caused an increase in uptake and notably lowered the efflux rate of rhodamine 123. Decreased expression of P-glycoprotein by compound 1 was detected by immunofluorescence flow cytometry after incubation with an anti-P-gp monoclonal antibody. These results suggest that resin glycosides represent potential efflux pump inhibitors for overcoming MDR in cancer therapy.

  20. Substrate recognition by glycoside hydrolase family 74 xyloglucanase from the basidiomycete Phanerochaete chrysosporium.

    Science.gov (United States)

    Ishida, Takuya; Yaoi, Katsuro; Hiyoshi, Ayako; Igarashi, Kiyohiko; Samejima, Masahiro

    2007-11-01

    The basidiomycete Phanerochaete chrysosporium produces xyloglucanase Xgh74B, which has the glycoside hydrolase (GH) family 74 catalytic domain and family 1 carbohydrate-binding module, in cellulose-grown culture. The recombinant enzyme, which was heterologously expressed in the yeast Pichia pastoris, had high hydrolytic activity toward xyloglucan from tamarind seed (TXG), whereas other beta-1,4-glucans examined were poor substrates for the enzyme. The existence of the carbohydrate-binding module significantly affects adsorption of the enzyme on crystalline cellulose, but has no effect on the hydrolysis of xyloglucan, indicating that the domain may contribute to the localization of the enzyme. HPLC and MALDI-TOF MS analyses of the hydrolytic products of TXG clearly indicated that Xgh74B hydrolyzes the glycosidic bonds of unbranched glucose residues, like other GH family 74 xyloglucanases. However, viscometric analysis suggested that Xgh74B hydrolyzes TXG in a different manner from other known GH family 74 xyloglucanases. Gel permeation chromatography showed that Xgh74B initially produced oligosaccharides of degree of polymerization (DP) 16-18, and these oligosaccharides were then slowly hydrolyzed to final products of DP 7-9. In addition, the ratio of oligosaccharides of DP 7-9 versus those of DP 16-18 was dependent upon the pH of the reaction mixture, indicating that the affinity of Xgh74B for the oligosaccharides of DP 16-18 is affected by the ionic environment at the active site.

  1. Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity

    Directory of Open Access Journals (Sweden)

    Jie-Tao Pan

    2015-04-01

    Full Text Available Six pentasaccharide resin glycosides from Ipomoea cairica, including four new acylated pentasaccharide resin glycosides, namely cairicoside I–IV (1–4 and the two known compounds cairicoside A (5 and cairicoside C (6, were isolated from the aerial parts of Ipomoea cairica. Their structures were established by a combination of spectroscopic, including two dimensional (2D NMR and chemical methods. The core of the six compounds was simonic acid A, and they were esterfied the same sites, just differing in the substituent groups. The lactonization site of the aglycone was bonded to the second saccharide moiety at C-2 in 1–4, and at C-3 in 5–6. Compounds 1 and 5, 4 and 6 were two pairs of isomers. The absolute configuration of the aglycone in 1–6 which was (11S-hydroxyhexadecanoic acid (jalapinolic acid was established by Mosher’s method. Compounds 1–4 have been evaluated for inhibitory activity against α-glucosidase, which all showed inhibitory activities.

  2. Comparative Analysis of Glycoside Hydrolases Activities from Phylogenetically Diverse Marine Bacteria of the Genus Arenibacter

    Directory of Open Access Journals (Sweden)

    Valery Mikhailov

    2013-06-01

    Full Text Available A total of 16 marine strains belonging to the genus Arenibacter, recovered from diverse microbial communities associated with various marine habitats and collected from different locations, were evaluated in degradation of natural polysaccharides and chromogenic glycosides. Most strains were affiliated with five recognized species, and some presented three new species within the genus Arenibacter. No strains contained enzymes depolymerizing polysaccharides, but synthesized a wide spectrum of glycosidases. Highly active β-N-acetylglucosaminidases and α-N-acetylgalactosaminidases were the main glycosidases for all Arenibacter. The genes, encoding two new members of glycoside hydrolyses (GH families, 20 and 109, were isolated and characterized from the genomes of Arenibacter latericius. Molecular genetic analysis using glycosidase-specific primers shows the absence of GH27 and GH36 genes. A sequence comparison with functionally-characterized GH20 and GH109 enzymes shows that both sequences are closest to the enzymes of chitinolytic bacteria Vibrio furnissii and Cellulomonas fimi of marine and terrestrial origin, as well as human pathogen Elisabethkingia meningoseptica and simbionts Akkermansia muciniphila, gut and non-gut Bacteroides, respectively. These results revealed that the genus Arenibacter is a highly taxonomic diverse group of microorganisms, which can participate in degradation of natural polymers in marine environments depending on their niche and habitat adaptations. They are new prospective candidates for biotechnological applications due to their production of unique glycosidases.

  3. Comparative Analysis of Glycoside Hydrolases Activities from Phylogenetically Diverse Marine Bacteria of the Genus Arenibacter

    Science.gov (United States)

    Bakunina, Irina; Nedashkovskaya, Olga; Balabanova, Larissa; Zvyagintseva, Tatyana; Rasskasov, Valery; Mikhailov, Valery

    2013-01-01

    A total of 16 marine strains belonging to the genus Arenibacter, recovered from diverse microbial communities associated with various marine habitats and collected from different locations, were evaluated in degradation of natural polysaccharides and chromogenic glycosides. Most strains were affiliated with five recognized species, and some presented three new species within the genus Arenibacter. No strains contained enzymes depolymerizing polysaccharides, but synthesized a wide spectrum of glycosidases. Highly active β-N-acetylglucosaminidases and α-N-acetylgalactosaminidases were the main glycosidases for all Arenibacter. The genes, encoding two new members of glycoside hydrolyses (GH) families, 20 and 109, were isolated and characterized from the genomes of Arenibacter latericius. Molecular genetic analysis using glycosidase-specific primers shows the absence of GH27 and GH36 genes. A sequence comparison with functionally-characterized GH20 and GH109 enzymes shows that both sequences are closest to the enzymes of chitinolytic bacteria Vibrio furnissii and Cellulomonas fimi of marine and terrestrial origin, as well as human pathogen Elisabethkingia meningoseptica and simbionts Akkermansia muciniphila, gut and non-gut Bacteroides, respectively. These results revealed that the genus Arenibacter is a highly taxonomic diverse group of microorganisms, which can participate in degradation of natural polymers in marine environments depending on their niche and habitat adaptations. They are new prospective candidates for biotechnological applications due to their production of unique glycosidases. PMID:23752354

  4. Absorption and tissue distribution of dietary quercetin and quercetin glycosides of apple skin in broiler chickens.

    Science.gov (United States)

    Rupasinghe, H P Vasantha; Ronalds, Clinton M; Rathgeber, Bruce; Robinson, Robin A

    2010-05-01

    Apple skins are a rich source of flavonols, in particular quercetin (Q) glycosides. The objective of the present study was to investigate the presence of Q metabolites in plasma, various tissues, and excreta when the commercial broiler chicken's diet was supplemented with Q (0, 50, 150, 300, or 600 mg kg(-1) body weight per day), an apple skin extract (ASE; 50, 150 mg total phenolics kg(-1) body weight per day), or a dried apple skin powder (ASP; 50 mg total phenolics kg(-1) body weight per day). When Q was supplemented for 3 days, Q sulfate, Q glucuronide, Q glucoside glucuronide, Q glucoside sulfate, and isorhamnetin glucoside were detected by liquid chromatography-tandem mass spectrometry in the liver and duodenum. Deconjugated Q was also detected in the breast and thigh tissues of ASE- and ASP-supplemented broilers. Regardless of the source or concentration of Q, the antioxidant capacity measured by ferric reducing ability of plasma (FRAP) assay in the plasma and tissues of the broilers did not change significantly. As far as is known, this is the first report to demonstrate that Q and its glycosides can be absorbed and metabolized by broiler chickens.

  5. Targeted Discovery of Glycoside Hydrolases from a Switchgrass-Adapted Compost Community

    Energy Technology Data Exchange (ETDEWEB)

    Reddy, Amitha; Allgaier, Martin; Park, Joshua I.; Ivanoval, Natalia; Dhaeseleer, Patrik; Lowry, Steve; Sapra, Rajat; Hazen, Terry C.; Simmons, Blake A.; VanderGheynst, Jean S.; Hugenholtz, Philip

    2011-05-11

    Development of cellulosic biofuels from non-food crops is currently an area of intense research interest. Tailoring depolymerizing enzymes to particular feedstocks and pretreatment conditions is one promising avenue of research in this area. Here we added a green-waste compost inoculum to switchgrass (Panicum virgatum) and simulated thermophilic composting in a bioreactor to select for a switchgrass-adapted community and to facilitate targeted discovery of glycoside hydrolases. Smallsubunit (SSU) rRNA-based community profiles revealed that the microbial community changed dramatically between the initial and switchgrass-adapted compost (SAC) with some bacterial populations being enriched over 20-fold. We obtained 225 Mbp of 454-titanium pyrosequence data from the SAC community and conservatively identified 800 genes encoding glycoside hydrolase domains that were biased toward depolymerizing grass cell wall components. Of these, ,10percent were putative cellulasesmostly belonging to families GH5 and GH9. We synthesized two SAC GH9 genes with codon optimization for heterologous expression in Escherichia coli and observed activity for one on carboxymethyl cellulose. The active GH9 enzyme has a temperature optimum of 50uC and pH range of 5.5 to 8 consistent with the composting conditions applied. We demonstrate that microbial communities adapt to switchgrass decomposition using simulated composting condition and that full-length genes can be identified from complex metagenomic sequence data, synthesized and expressed resulting in active enzyme.

  6. Targeted discovery of glycoside hydrolases from a switchgrass-adapted compost community

    Energy Technology Data Exchange (ETDEWEB)

    Allgaier, M.; Reddy, A.; Park, J. I.; Ivanova, N.; D' haeseleer, P.; Lowry, S.; Sapra, R.; Hazen, T.C.; Simmons, B.A.; VanderGheynst, J. S.; Hugenholtz, P.

    2009-11-15

    Development of cellulosic biofuels from non-food crops is currently an area of intense research interest. Tailoring depolymerizing enzymes to particular feedstocks and pretreatment conditions is one promising avenue of research in this area. Here we added a green-waste compost inoculum to switchgrass (Panicum virgatum) and simulated thermophilic composting in a bioreactor to select for a switchgrass-adapted community and to facilitate targeted discovery of glycoside hydrolases. Small-subunit (SSU) rRNA-based community profiles revealed that the microbial community changed dramatically between the initial and switchgrass-adapted compost (SAC) with some bacterial populations being enriched over 20-fold. We obtained 225 Mbp of 454-titanium pyrosequence data from the SAC community and conservatively identified 800 genes encoding glycoside hydrolase domains that were biased toward depolymerizing grass cell wall components. Of these, {approx}10% were putative cellulases mostly belonging to families GH5 and GH9. We synthesized two SAC GH9 genes with codon optimization for heterologous expression in Escherichia coli and observed activity for one on carboxymethyl cellulose. The active GH9 enzyme has a temperature optimum of 50 C and pH range of 5.5 to 8 consistent with the composting conditions applied. We demonstrate that microbial communities adapt to switchgrass decomposition using simulated composting condition and that full-length genes can be identified from complex metagenomic sequence data, synthesized and expressed resulting in active enzyme.

  7. Topical anti-inflammatory effects of isorhamnetin glycosides isolated from Opuntia ficus-indica.

    Science.gov (United States)

    Antunes-Ricardo, Marilena; Gutiérrez-Uribe, Janet A; Martínez-Vitela, Carlos; Serna-Saldívar, Sergio O

    2015-01-01

    Opuntia ficus-indica (OFI) has been widely used in Mexico as a food and for the treatment of different health disorders such as inflammation and skin aging. Its biological properties have been attributed to different phytochemicals such as the isorhamnetin glycosides which are the most abundant flavonoids. Moreover, these compounds are considered a chemotaxonomic characteristic of OFI species. The aim of this study was to evaluate the effect of OFI extract and its isorhamnetin glycosides on different inflammatory markers in vitro and in vivo. OFI extract was obtained by alkaline hydrolysis of OFI cladodes powder and pure compounds were obtained by preparative chromatography. Nitric oxide (NO), cyclooxygenase-2 (COX-2), tumor necrosis factor- (TNF-) α, and interleukin- (IL-) 6 production were measured. NO production was tested in lipopolysaccharide-stimulated RAW 264.7 cells while in vivo studies were carried on croton oil-induced ear edema model. OFI extract and diglycoside isorhamnetin-glucosyl-rhamnoside (IGR) at 125 ng/mL suppressed the NO production in vitro (73.5 ± 4.8% and 68.7 ± 5.0%, resp.) without affecting cell viability. Likewise, IGR inhibited the ear edema (77.4 ± 5.7%) equating the indomethacin effects (69.5 ± 5.3%). Both IGR and OFI extract significantly inhibited the COX-2, TNF-α, and IL-6 production. IGR seems to be a suitable natural compound for development of new anti-inflammatory ingredient.

  8. Topical Anti-Inflammatory Effects of Isorhamnetin Glycosides Isolated from Opuntia ficus-indica

    Directory of Open Access Journals (Sweden)

    Marilena Antunes-Ricardo

    2015-01-01

    Full Text Available Opuntia ficus-indica (OFI has been widely used in Mexico as a food and for the treatment of different health disorders such as inflammation and skin aging. Its biological properties have been attributed to different phytochemicals such as the isorhamnetin glycosides which are the most abundant flavonoids. Moreover, these compounds are considered a chemotaxonomic characteristic of OFI species. The aim of this study was to evaluate the effect of OFI extract and its isorhamnetin glycosides on different inflammatory markers in vitro and in vivo. OFI extract was obtained by alkaline hydrolysis of OFI cladodes powder and pure compounds were obtained by preparative chromatography. Nitric oxide (NO, cyclooxygenase-2 (COX-2, tumor necrosis factor- (TNF- α, and interleukin- (IL- 6 production were measured. NO production was tested in lipopolysaccharide-stimulated RAW 264.7 cells while in vivo studies were carried on croton oil-induced ear edema model. OFI extract and diglycoside isorhamnetin-glucosyl-rhamnoside (IGR at 125 ng/mL suppressed the NO production in vitro (73.5 ± 4.8% and 68.7±5.0%, resp. without affecting cell viability. Likewise, IGR inhibited the ear edema (77.4±5.7% equating the indomethacin effects (69.5±5.3%. Both IGR and OFI extract significantly inhibited the COX-2, TNF-α, and IL-6 production. IGR seems to be a suitable natural compound for development of new anti-inflammatory ingredient.

  9. Transcriptome and Metabolite analysis reveal candidate genes of the cardiac glycoside biosynthetic pathway from Calotropis procera.

    Science.gov (United States)

    Pandey, Akansha; Swarnkar, Vishakha; Pandey, Tushar; Srivastava, Piush; Kanojiya, Sanjeev; Mishra, Dipak Kumar; Tripathi, Vineeta

    2016-10-05

    Calotropis procera is a medicinal plant of immense importance due to its pharmaceutical active components, especially cardiac glycosides (CG). As genomic resources for this plant are limited, the genes involved in CG biosynthetic pathway remain largely unknown till date. Our study on stage and tissue specific metabolite accumulation showed that CG's were maximally accumulated in stems of 3 month old seedlings. De novo transcriptome sequencing of same was done using high throughput Illumina HiSeq platform generating 44074 unigenes with average mean length of 1785 base pair. Around 66.6% of unigenes were annotated by using various public databases and 5324 unigenes showed significant match in the KEGG database involved in 133 different pathways of plant metabolism. Further KEGG analysis resulted in identification of 336 unigenes involved in cardenolide biosynthesis. Tissue specific expression analysis of 30 putative transcripts involved in terpenoid, steroid and cardenolide pathways showed a positive correlation between metabolite and transcript accumulation. Wound stress elevated CG levels as well the levels of the putative transcripts involved in its biosynthetic pathways. This result further validated the involvement of identified transcripts in CGs biosynthesis. The identified transcripts will lay a substantial foundation for further research on metabolic engineering and regulation of cardiac glycosides biosynthesis pathway genes.

  10. The first alpha-1,3-glucosidase from bacterial origin belonging to glycoside hydrolase family 31.

    Science.gov (United States)

    Kang, Min-Sun; Okuyama, Masayuki; Mori, Haruhide; Kimura, Atsuo

    2009-01-01

    Genome analysis of Lactobacillus johnsonii NCC533 has been recently completed. One of its annotated genes, lj0569, encodes the protein having the conserved domain of glycoside hydrolase family 31. Its homolog gene (ljag31) in L. johnsonii NBRC13952 was cloned and expressed using an Escherichia coli expression system, resulting in poor production of recombinant LJAG31 protein due to inclusion body formation. Production of soluble recombinant LJAG31 was improved with high concentration of NaCl in medium, possible endogenous chaperone induction by benzyl alcohol, and over-expression of GroES-GroEL chaperones. Recombinant LJAG31 was an alpha-glucosidase with broad substrate specificity toward both homogeneous and heterogeneous substrates. This enzyme displayed higher specificity (in terms of k(cat)/K(m)) toward nigerose, maltulose, and kojibiose than other natural substrates having an alpha-glucosidic linkage at the non-reducing end, which suggests that these sugars are candidates for prebiotics contributing to the growth of L. johnsonii. To our knowledge, LJAG31 is the first bacterial alpha-1,3-glucosidase to be characterized with a high k(cat)/K(m) value for nigerose [alpha-d-Glcp-(1 --> 3)-d-Glcp]. Transglucosylation of 4-nitrophenyl alpha-d-glucopyranoside produced two 4-nitrophenyl disaccharides (4-nitrophenyl alpha-nigeroside and 4-nitrophenyl alpha-isomaltoside). These hydrolysis and transglucosylation properties of LJAG31 are different from those of mold (Acremonium implicatum) alpha-1,3-glucosidase of glycoside hydrolase family 31.

  11. Biogenesis of C-Glycosyl Flavones and Profiling of Flavonoid Glycosides in Lotus (Nelumbo nucifera)

    Science.gov (United States)

    Li, Shan-Shan; Wu, Jie; Chen, Li-Guang; Du, Hui; Xu, Yan-Jun; Wang, Li-Jing; Zhang, Hui-Jin; Zheng, Xu-Chen; Wang, Liang-Sheng

    2014-01-01

    Flavonoids in nine tissues of Nelumbo nucifera Gaertner were identified and quantified by high-performance liquid chromatography with diode array detector (HPLC-DAD) and HPLC-electrospray ionization-mass spectrometry (HPLC-ESI-MSn). Thirty-eight flavonoids were identified; eleven C-glycosides and five O-glycosides were discovered for the first time in N. nucifera. Most importantly, the C-glycosyl apigenin or luteolin detected in lotus plumules proved valuable for deep elucidation of flavonoid composition in lotus tissues and for further utilization as functional tea and medicine materials. Lotus leaves possessed the significantly highest amount of flavonoids (2.06E3±0.08 mg 100 g−1 FW) and separating and purifying the bioactive compound, quercetin 3-O-glucuronide, from leaves showed great potential. In contrast, flavonoids in flower stalks, seed coats and kernels were extremely low. Simultaneously, the optimal picking time was confirmed by comparing the compound contents in five developmental phases. Finally, we proposed the putative flavonoid biosynthesis pathway in N. nucifera. PMID:25279809

  12. Differential Recognition and Hydrolysis of Host Carbohydrate Antigens by Streptococcus pneumoniae Family 98 Glycoside Hydrolases

    Energy Technology Data Exchange (ETDEWEB)

    Higgins, M.; Whitworth, G; El Warry, N; Randriantsoa, M; Samain, E; Burke, R; Vocadlo, D; Boraston, A

    2009-01-01

    The presence of a fucose utilization operon in the Streptococcus pneumoniae genome and its established importance in virulence indicates a reliance of this bacterium on the harvesting of host fucose-containing glycans. The identities of these glycans, however, and how they are harvested is presently unknown. The biochemical and high resolution x-ray crystallographic analysis of two family 98 glycoside hydrolases (GH98s) from distinctive forms of the fucose utilization operon that originate from different S. pneumoniae strains reveal that one enzyme, the predominant type among pneumococcal isolates, has a unique endo-{beta}-galactosidase activity on the LewisY antigen. Altered active site topography in the other species of GH98 enzyme tune its endo-{beta}-galactosidase activity to the blood group A and B antigens. Despite their different specificities, these enzymes, and by extension all family 98 glycoside hydrolases, use an inverting catalytic mechanism. Many bacterial and viral pathogens exploit host carbohydrate antigens for adherence as a precursor to colonization or infection. However, this is the first evidence of bacterial endoglycosidase enzymes that are known to play a role in virulence and are specific for distinct host carbohydrate antigens. The strain-specific distribution of two distinct types of GH98 enzymes further suggests that S. pneumoniae strains may specialize to exploit host-specific antigens that vary from host to host, a factor that may feature in whether a strain is capable of colonizing a host or establishing an invasive infection.

  13. A new resin glycoside from Calystegia soldanella and its antiviral activity towards herpes.

    Science.gov (United States)

    Ono, Masateru; Kanemaru, Yukiyo; Yasuda, Shin; Okawa, Masafumi; Kinjo, Junei; Miyashita, Hiroyuki; Yokomizo, Kazumi; Yoshimitsu, Hitoshi; Nohara, Toshihiro

    2017-11-01

    A new resin glycoside, named calysolin XVIII (1), was isolated from the leaves, stems and roots of Calystegia soldanella Roem. et Schult. (Convolvulaceae). The structure of 1 was defined as 11S-jalapinolic acid 11-O-β-d-glucopyranosyl-(1 → 3)-O-(2-O-2S-methylbutyryl,4-O-3-hydroxy-2-methylenebutyryl)-α-l-rhamnopyranosyl-(1 → 2)-[O-β-d-glucopyranosyl-(1 → 6)-O-(34-di-O-2S-methylbutyryl)-β-d-glucopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 2)-β-d-quinovopyranoside, intramolecular 1,2″'″'-ester on the basis of spectroscopic data. Compound 1 is the first known resin glycoside to feature 3-hydroxy-2-methylenebutyric acid as a component organic acid. In addition, 1 demonstrated an antiviral activity against herpes simplex virus type 1, with an IC 50 value 2.3 μM.

  14. Zebrafish bioassay-guided microfractionation identifies anticonvulsant steroid glycosides from the Philippine medicinal plant Solanum torvum.

    Science.gov (United States)

    Challal, Soura; Buenafe, Olivia E M; Queiroz, Emerson F; Maljevic, Snezana; Marcourt, Laurence; Bock, Merle; Kloeti, Werner; Dayrit, Fabian M; Harvey, Alan L; Lerche, Holger; Esguerra, Camila V; de Witte, Peter A M; Wolfender, Jean-Luc; Crawford, Alexander D

    2014-10-15

    Medicinal plants used for the treatment of epilepsy are potentially a valuable source of novel antiepileptic small molecules. To identify anticonvulsant secondary metabolites, we performed an in vivo, zebrafish-based screen of medicinal plants used in Southeast Asia for the treatment of seizures. Solanum torvum Sw. (Solanaceae) was identified as having significant anticonvulsant activity in zebrafish larvae with seizures induced by the GABAA antagonist pentylenetetrazol (PTZ). This finding correlates well with the ethnomedical use of this plant in the Philippines, where a water decoction of S. torvum leaves is used to treat epileptic seizures. HPLC microfractionation of the bioactive crude extract, in combination with the in vivo zebrafish seizure assay, enabled the rapid localization of several bioactive compounds that were partially identified online by UHPLC-TOF-MS as steroid glycosides. Targeted isolation of the active constituents from the methanolic extract enabled the complete de novo structure identification of the six main bioactive compounds that were also present in the traditional preparation. To partially mimic the in vivo metabolism of these triterpene glycosides, their common aglycone was generated by acid hydrolysis. The isolated molecules exhibited significant anticonvulsant activity in zebrafish seizure assays. These results underscore the potential of zebrafish bioassay-guided microfractionation to rapidly identify novel bioactive small molecules of natural origin.

  15. Identification, quantification, and sensory characterization of steviol glycosides from differently processed Stevia rebaudiana commercial extracts.

    Science.gov (United States)

    Espinoza, María Inés; Vincken, Jean-Paul; Sanders, Mark; Castro, Cristian; Stieger, Markus; Agosin, Eduardo

    2014-12-10

    Stevia rebaudiana is known for its sweet-tasting ent-kaurene diterpenoid glycosides. Several manufacturing strategies are currently employed to obtain Stevia sweeteners with the lowest possible off-flavors. The chemical composition of four commercial S. rebaudiana extracts, obtained by different technologies, was characterized using UHPLC-ESI-MS(n). The composition of one of the ethanol-crystallized extracts (EC2) was entirely rebaudioside A, whereas the enzymatically modified (EM) extract contained the lowest concentration of this compound (2.7 mg/100 mg). The membrane-purified (MP) extract had the highest content of minor natural steviol glycosides (23.7 mg/100 mg total extract) versus an average of 2.4 mg/100 mg total extract for the EC samples. Thirteen trained panelists evaluated sweetness, bitterness, licorice, and metallic attributes of all four extracts. The highest licorice intensity (p ≤ 0.05) was found for MP. Both samples EC1 and EC2, despite their different chemical compositions, showed no significant differences in sensory perception.

  16. Response surface methodology to optimise Accelerated Solvent Extraction of steviol glycosides from Stevia rebaudiana Bertoni leaves.

    Science.gov (United States)

    Jentzer, Jean-Baptiste; Alignan, Marion; Vaca-Garcia, Carlos; Rigal, Luc; Vilarem, Gérard

    2015-01-01

    Following the approval of steviol glycosides as a food additive in Europe in December 2011, large-scale stevia cultivation will have to be developed within the EU. Thus there is a need to increase the efficiency of stevia evaluation through germplasm enhancement and agronomic improvement programs. To address the need for faster and reproducible sample throughput, conditions for automated extraction of dried stevia leaves using Accelerated Solvent Extraction were optimised. A response surface methodology was used to investigate the influence of three factors: extraction temperature, static time and cycle number on the stevioside and rebaudioside A extraction yields. The model showed that all the factors had an individual influence on the yield. Optimum extraction conditions were set at 100 °C, 4 min and 1 cycle, which yielded 91.8% ± 3.4% of total extractable steviol glycosides analysed. An additional optimisation was achieved by reducing the grind size of the leaves giving a final yield of 100.8% ± 3.3%. Copyright © 2014 Elsevier Ltd. All rights reserved.

  17. Influence of drying method on steviol glycosides and antioxidants in Stevia rebaudiana leaves.

    Science.gov (United States)

    Periche, Angela; Castelló, María Luisa; Heredia, Ana; Escriche, Isabel

    2015-04-01

    The application of different drying conditions (hot air drying at 100 °C and 180 °C, freeze drying and shade drying) on steviol glycosides (stevioside, dulcoside A, rebaudioside A and rebaudioside C) and antioxidants in Stevia leaves was evaluated. Stevioside, the major glycoside found in fresh leaves (81.2mg/g), suffered an important reduction in all cases, although shade drying was the least aggressive treatment. Considering the antioxidant parameters (total phenols, flavonoids and total antioxidants), the most suitable drying method was hot air at 180 °C, since it substantially increased all of them (76.8 mg gallic acid, 45.1mg catechin and 126 mg Trolox, all equivalent/g Stevia, respectively), with respect to those present in fresh leaves (44.4, 2.5 and 52.9 mg equivalent/g). Therefore, the ideal method for drying Stevia leaves depends on their final use (sweetener or antioxidant), although, hot air at 180 °C is the most recommendable if only one treatment has to be chosen. Copyright © 2014 Elsevier Ltd. All rights reserved.

  18. COMPARATIVE MODELLING AND LIGAND BINDING SITE PREDICTION OF A FAMILY 43 GLYCOSIDE HYDROLASE FROM Clostridium thermocellum

    Directory of Open Access Journals (Sweden)

    Shadab Ahmed

    2012-06-01

    Full Text Available The phylogenetic analysis of Clostridium thermocellum family 43 glycoside hydrolase (CtGH43 showed close evolutionary relation with carbohydrate binding family 6 proteins from C. cellulolyticum, C. papyrosolvens, C. cellulyticum, and A. cellulyticum. Comparative modeling of CtGH43 was performed based on crystal structures with PDB IDs 3C7F, 1YIF, 1YRZ, 2EXH and 1WL7. The structure having lowest MODELLER objective function was selected. The three-dimensional structure revealed typical 5-fold beta–propeller architecture. Energy minimization and validation of predicted model with VERIFY 3D indicated acceptability of the proposed atomic structure. The Ramachandran plot analysis by RAMPAGE confirmed that family 43 glycoside hydrolase (CtGH43 contains little or negligible segments of helices. It also showed that out of 301 residues, 267 (89.3% were in most favoured region, 23 (7.7% were in allowed region and 9 (3.0% were in outlier region. IUPred analysis of CtGH43 showed no disordered region. Active site analysis showed presence of two Asp and one Glu, assumed to form a catalytic triad. This study gives us information about three-dimensional structure and reaffirms the fact that it has the similar core 5-fold beta–propeller architecture and so probably has the same inverting mechanism of action with the formation of above mentioned catalytic triad for catalysis of polysaccharides.

  19. Production of oleanolic acid glycosides by hairy root established cultures of Calendula officinalis L.

    Science.gov (United States)

    Długosz, Marek; Wiktorowska, Ewa; Wiśniewska, Anita; Pączkowski, Cezary

    2013-01-01

    In order to initiate hairy root culture initiation cotyledons and hypocotyls of Calendula officinalis L. were infected with Agrobacterium rhizogenes strain ATCC 15834 or the same strain containing pCAMBIA 1381Z vector with β-glucuronidase reporter gene under control of promoter of NIK (Nematode Induced Kinase) gene. The efficiency of induction of hairy roots reached 33.8% for cotyledons and 66.6% for hypocotyls together for both transformation experiments. Finally, eight control and nine modified lines were established as a long-term culture. The hairy root cultures showed the ability to synthesize oleanolic acid mainly (97%) as glycosides; control lines contained it at the average 8.42 mg · g(-1) dry weight in tissue and 0.23 mg · dm(-3) in medium; modified lines: 4.59 mg · g(-1) for the tissue, and 0.48 mg · dm(-3) for the medium. Additionally lines showed high positive correlation between dry/fresh weight and oleanolic acid concentration in tissue. Using the Killiani mixture in acidic hydrolysis of oleanolic acid glycosides released free aglycones that were partially acetylated in such conditions.

  20. Antiproliferative Activity of Triterpene Glycoside Nutrient from Monk Fruit in Colorectal Cancer and Throat Cancer

    Directory of Open Access Journals (Sweden)

    Can Liu

    2016-06-01

    Full Text Available Colorectal cancer and throat cancer are the world’s most prevalent neoplastic diseases, and a serious threat to human health. Plant triterpene glycosides have demonstrated antitumor activity. In this study, we investigated potential anticancer effects of mogroside IVe, a triterpenoid glycoside from monk fruit, using in vitro and in vivo models of colorectal and laryngeal cancer. The effects of mogroside IVe on the proliferation of colorectal cancer HT29 cells and throat cancer Hep-2 cells were determined by 3-(4,5-dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide (MTT assay, and the expression levels of p53, phosphorylated ERK1/2, and MMP-9 were analyzed by western blotting and immunohistochemistry. The results indicated that mogroside IVe inhibited, in a dose-dependent manner, the proliferation of HT29 and Hep-2 cells in culture and in xenografted mice, which was accompanied by the upregulation of tumor suppressor p53, and downregulation of matrix metallopeptidase 9 (MMP-9 and phosphorylated extracellular signal-regulated kinases (ERK1/2. This study revealed the suppressive activity of mogroside IVe towards colorectal and throat cancers and identified the underlying mechanisms, suggesting that mogroside IVe may be potentially used as a biologically-active phytochemical supplement for treating colorectal and throat cancers.

  1. Identification and quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of Pistacia lentiscus L.

    Science.gov (United States)

    Romani, A; Pinelli, P; Galardi, C; Mulinacci, N; Tattini, M

    2002-01-01

    Separation, identification and quantification of polyphenols was carried out on leaves of Pistacia lentiscus L., an evergreen member of the family Anacardiaceae, using semi-preparative HPLC, HPLC-photodiode array detection and HPLC-MS analysis, together with 1H- and 13C NMR. Three major classes of secondary metabolites were detected: (i) gallic acid and galloyl derivatives of both glucose and quinic acid; (ii) flavonol glycosides, i.e. myricetin and quercetin glycosides; and (iii) anthocyanins, namely delphinidin 3-O-glucoside and cyanidin 3-O-glucoside. Low amounts of catechin were also detected. The concentration of galloyl derivatives was extremely high, representing 5.3% of the leaf dry weight, and appreciable amounts of myricetin derivatives were also detected (1.5% on a dry weight basis). These findings may be useful in establishing a relationship between the chemical composition of the leaf extract and the previously reported biological activity of P. lentiscus, and may also assign a new potential role of P. lentiscus tissue extracts in human health care.

  2. Anthenosides L-U, Steroidal Glycosides with Unusual Structural Features from the Starfish Anthenea aspera.

    Science.gov (United States)

    Malyarenko, Timofey V; Kharchenko, Sofiya D; Kicha, Alla A; Ivanchina, Natalia V; Dmitrenok, Pavel S; Chingizova, Ekaterina A; Pislyagin, Evgeny A; Evtushenko, Evgeny V; Antokhina, Tatyana I; Minh, Chau Van; Stonik, Valentin A

    2016-12-23

    Ten new polyhydroxysteroidal glycosides, anthenosides L-U (1-10), with rare positions of carbohydrate fragment attachments, were isolated from the starfish Anthenea aspera. The structures of 1-10 were established by NMR and ESIMS techniques as well as by chemical transformations. The unoxidized Δ(22)-24-nor-cholestane (1), (24S)-Δ(22)-24-methylcholestane (2-5), and Δ(22)-cholestane (7) side chains of the steroidal aglycons, 3-O-methyl-β-d-galactofuranosyl residue (2, 8), and 5α-cholest-8(14)-ene-3α,7β,16α-trihydroxysteroidal nucleus (9, 10) have not been found previously in starfish polar steroidal compounds. The mixture of glycosides 9 and 10 showed hemolytic activity with an EC50 = 8 μM. Compound 4 at a dose of 10 μM exhibited a potential immunomodulatory action, decreasing by 24% the intracellular ROS content in RAW 264.7 murine macrophages, induced by pro-inflammatory endotoxic lipopolysaccharide from E. coli.

  3. Flavone glycosides from commercially available Lophatheri Herba and their chromatographic fingerprinting and quantitation

    Directory of Open Access Journals (Sweden)

    Jyun-Siang Fan

    2015-12-01

    Full Text Available Lophatheri Herba (Danzhuye; LH, the dried leaves of Lophatherum gracile Brongn (Poaceae, is commonly used in Chinese herbal medicine as an antipyretic, antibacterial, and diuretic. Chemical analysis has been conducted to isolate and identify seven major flavonoid glycosides, including a new flavone C-glycoside, luteolin 6-C-β-D-glucuronopyranosyl-(1→2-β-D-glucopyranoside (1, isoorientin (2, swertiajaponin (3, luteolin 6-C-β-D-glucuronopyranosyl-(1→2-α-L-arabinopyranoside (4, isovitexin (5, swertisin (6, luteolin 7-O-β-D-glucopyranoside (7, and luteolin 6-C-α-L-arabinopyranoside (8, from commercially available LHs in Taiwan. The structure of the new compound (1, the maximum component, was determined by extensive one- (1D- and two-dimensional (2D- nuclear magnetic resonance (NMR, and MS spectral analyses. The 1H and 13C-NMR of two rotameric pairs of 3 and 6 were also assigned. To establish the quality control platform of LH, we developed a simultaneous determination of multiple components in 10 commercially available LHs, collected from different areas of Taiwan, by high performance liquid chromatography (HPLC and ultra performance liquid chromatography (UPLC, as well as quantitative measurement of the major components 1–4, and 8. All isolated major compounds showed good linear regression (R2 ≥ 0.9993 within the test ranges and high reproducibility. These methods are readily accessible for the quality control of LH.

  4. Flavone glycosides from commercially available Lophatheri Herba and their chromatographic fingerprinting and quantitation.

    Science.gov (United States)

    Fan, Jyun-Siang; Lee, I-Jung; Lin, Yun-Lian

    2015-12-01

    Lophatheri Herba (Danzhuye; LH), the dried leaves of Lophatherum gracile Brongn (Poaceae), is commonly used in Chinese herbal medicine as an antipyretic, antibacterial, and diuretic. Chemical analysis has been conducted to isolate and identify seven major flavonoid glycosides, including a new flavone C-glycoside, luteolin 6-C-β-D-glucuronopyranosyl-(1→2)-β-D-glucopyranoside (1), isoorientin (2), swertiajaponin (3), luteolin 6-C-β-D-glucuronopyranosyl-(1→2)-α-L-arabinopyranoside (4), isovitexin (5), swertisin (6), luteolin 7-O-β-D-glucopyranoside (7), and luteolin 6-C-α-L-arabinopyranoside (8), from commercially available LHs in Taiwan. The structure of the new compound (1), the maximum component, was determined by extensive one- (1D-) and two-dimensional (2D-) nuclear magnetic resonance (NMR), and MS spectral analyses. The (1)H and (13)C-NMR of two rotameric pairs of 3 and 6 were also assigned. To establish the quality control platform of LH, we developed a simultaneous determination of multiple components in 10 commercially available LHs, collected from different areas of Taiwan, by high performance liquid chromatography (HPLC) and ultra performance liquid chromatography (UPLC), as well as quantitative measurement of the major components 1-4, and 8. All isolated major compounds showed good linear regression (R(2) ≥ 0.9993) within the test ranges and high reproducibility. These methods are readily accessible for the quality control of LH. Copyright © 2015. Published by Elsevier B.V.

  5. Extraction of Stevia rebaudiana bertoni sweetener glycosides by supercritical fluid methods.

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    Juan José Hinojosa-González

    2017-05-01

    Full Text Available Aim. The aim was to evaluate the supercritical carbon dioxide extraction method with and without the addition of co-solvent to the system (mixture water: ethanol to obtain the glycosides from leaves of Stevia rebaudiana Bertoni. Methods. A SFT-150 SFE / SFR model with CO2 as a fluid was used for the supercritical extraction. The variables studied were temperature, pressure, extraction time and the presence or absence of the co-solvent (water-ethanol mixture in a concentration of 70:30 v/v, incorporated in different proportions to determine the effect on yield. The amount of glycoside sweeteners was analyzed by High Performance Liquid Chromatography (HPLC. Results. The pressure was the factor that favored the extraction, which was selective in obtaining Rebaudioside A with yields no greater than 2%. The inclusion of the co-solvent achieved an increase in yield to values of 2.9% Conclusion. Supercritical CO2 individually and mixed with ethanol-water as a co-solvent was not efficient to extract Stevia rebaudiana stevioside sweeteners

  6. Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis.

    Science.gov (United States)

    Morikawa, Toshio; Ninomiya, Kiyofumi; Kuramoto, Hiroyuki; Kamei, Iyori; Yoshikawa, Masayuki; Muraoka, Osamu

    2016-01-01

    A methanol extract of the flowers of Narcissus tazetta var. chinensis Roem. (Amaryllidaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, four new phenylethanoid glycosides, tazettosides A–D (1–4), and a new phenylpropanoid glycoside, tazettoside E (5), were isolated along with 23 known compounds (6–28). Of the isolates, 1 (IC50 = 22.0 μM) and 4 (82.5 μM), 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (13, IC50 = 28.5 μM), 5,6-dihydrobicolorine (14, 23.7 μM), tazettine (16, 60.8 μM), benzyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (18, 27.8 μM), 2-(3,4-dimethoxyphenyl)ethyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (21, 74.6 μM), 3-phenylpropyl β-D-glucopyranoside (22, 59.0 μM), and cinnamyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (24, 88.0 μM) showed inhibitory effects without notable cytotoxicity at the effective concentrations.

  7. Identification of flavonol and xanthone glycosides from mango (Mangifera indica L. Cv. "Tommy Atkins") peels by high-performance liquid chromatography-electrospray ionization mass spectrometry.

    Science.gov (United States)

    Schieber, Andreas; Berardini, Nicolai; Carle, Reinhold

    2003-08-13

    Flavonol O- and xanthone C-glycosides were extracted from mango (Mangifera indica L. cv. "Tommy Atkins") peels and characterized by high-performance liquid chromatography-electrospray ionization mass spectrometry. Among the fourteen compounds analyzed, seven quercetin O-glycosides, one kaempferol O-glycoside, and four xanthone C-glycosides were found. On the basis of their fragmentation pattern, the latter were identified as mangiferin and isomangiferin and their respective galloyl derivatives. A flavonol hexoside with m/z 477 was tentatively identified as a rhamnetin glycoside, which to the best of our knowledge, has not yet been reported in mango peels. The results obtained in the present study confirm that peels originating from mango fruit processing are a promising source of phenolic compounds that might be recovered and used as natural antioxidants or functional food ingredients.

  8. Structural characterization of flavonoid C- and O-glycosides in an extract of Adhatoda vasica leaves by liquid chromatography with quadrupole time-of-flight mass spectrometry.

    Science.gov (United States)

    Singh, Awantika; Kumar, Sunil; Bajpai, Vikas; Reddy, T Jagadeshwar; Rameshkumar, K B; Kumar, Brijesh

    2015-06-30

    Adhatoda vasica Nees is a well-known Ayurvedic medicinal plant, belonging to the family Acanthaceae. This study aims to seek identification and characterization of flavonoid C- and O-glycosides in the aqueous fraction of the plant leaves. A method was developed for simultaneous characterization of flavonoids and their glycosides using high-pressure liquid chromatography with quadrupole time-of-flight mass spectrometry (HPLC/ESI-QTOF-MS/MS). The chromatographic separation was carried on an Agilent Poroshell 120 EC-C18 column (4.6 × 150 mm, 2.7 µm) operated with 0.1% formic acid aqueous solution and methanol as the mobile phase. The fragmentations of the studied [M-H](-) ions of C-glycosides were shown to be cross-ring cleavages of the glycoside moiety [M-H-(60/90/120)](-) whereas O-glycosides were shown to eliminate the sugar moiety (Y0 (-) or [Y0 -H](-) ) from the aglycone unit; 6-C-glycosides exhibited [M-H-18](-) , a characteristic ion, and also a higher abundance of (0,3) X6 or 8 ions in comparison to 8-C glycosides; flavonoid 6,8-di-C-glycosides exhibited cross-ring cleavages of the sugar attached to the C-6 position preferentially. This method was successfully applied for analysis of flavonoids and their glycosides in Adhatoda vasica leaves. A total of 29 compounds were tentatively identified including 17 C-, nine O-glycosides and three flavonoids. Copyright © 2015 John Wiley & Sons, Ltd.

  9. In silico analysis and expression profiling of miRNAs targeting genes of steviol glycosides biosynthetic pathway and their relationship with steviol glycosides content in different tissues of Stevia rebaudiana.

    Science.gov (United States)

    Saifi, Monica; Nasrullah, Nazima; Ahmad, Malik Mobeen; Ali, Athar; Khan, Jawaid A; Abdin, M Z

    2015-09-01

    miRNAs are emerging as potential regulators of the gene expression. Their proven promising role in regulating biosynthetic pathways related gene networks may hold the key to understand the genetic regulation of these pathways which may assist in selection and manipulation to get high performing plant genotypes with better secondary metabolites yields and increased biomass. miRNAs associated with genes of steviol glycosides biosynthetic pathway, however, have not been identified so far. In this study miRNAs targeting genes of steviol glycosides biosynthetic pathway were identified for the first time whose precursors were potentially generated from ESTs and nucleotide sequences of Stevia rebaudiana. Thereafter, stem-loop coupled real time PCR based expressions of these miRNAs in different tissues of Stevia rebaudiana were investigated and their relationship pattern was analysed with the expression levels of their target mRNAs as well as steviol glycoside contents. All the miRNAs investigated showed differential expressions in all the three tissues studied, viz. leaves, flowers and stems. Out of the eleven miRNAs validated, the expression levels of nine miRNAs (miR319a, miR319b, miR319c, miR319d, miR319e, miR319f, miR319h, miRstv_7, miRstv_9) were found to be inversely related, while expression levels of the two, i.e. miR319g and miRstv_11 on the contrary, showed direct relation with the expression levels of their target mRNAs and steviol glycoside contents in the leaves, flowers and stems. This study provides a platform for better understanding of the steviol glycosides biosynthetic pathway and these miRNAs can further be employed to manipulate the biosynthesis of these metabolites to enhance their contents and yield in S. rebaudiana. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

  10. Discovery of α-L-arabinopyranosidases from human gut microbiome expands the diversity within glycoside hydrolase family 42

    DEFF Research Database (Denmark)

    Viborg, Alexander Holm; Katayama, Takane; Arakawa, Takatoshi

    2017-01-01

    Enzymes of the glycoside hydrolase family 42 (GH42) are widespread in bacteria of the human gut microbiome and play fundamental roles in the decomposition of both milk and plant oligosaccharides. All GH42 enzymes characterized so far have β-galactosidase activity. Here, we report the existence...

  11. Acaricidal effects of cardiac glycosides, azadirachtin and neem oil against the camel tick, Hyalomma dromedarii (Acari: Ixodidae).

    Science.gov (United States)

    Al-Rajhy, DiefAlla H; Alahmed, Azzam M; Hussein, Hamdy I; Kheir, Salah M

    2003-11-01

    The cardiac glycoside, digitoxin, from Digitalis purpurea L (Scrophulariaceae), a cardiac glycosidal (cardenolide) extract from Calotropis procera (Ait) R Br (Asclepiadaceae), azadirachtin and neem oil from Azadirachta indica A Juss (Meliaceae) were tested for their effects against larvae and adult stages of the camel tick, Hyalomma dromedarii Koch (Acari: Ixodidae). The contact LC50 values of the first three materials against adults were 4.08, 9.63 and >40.7 microg cm(-2), respectively, whereas the dipping LC50 values of the four materials were 409.9, 1096, >5000 and >5000 mg litre(-1), respectively. Contact and dipping LC50 values of the extract and azadirachtin against larvae were 6.16, >20.3 microg cm(-2) and 587.7 and >2500 mg litre(-1), respectively. Azadirachtin had no effects on egg production or feeding of adults up to 5000 mg litre(-1); however at 2500 mg litre(-1), it caused significant reduction in feeding activity of larve, prolonged the period for moulting to nymphal stage, and caused 60% reduction in moultability. Results of the two cardiac glycoside materials are comparable with those of several commercial acaricides. The risks and benefits associated with the use of cardiac glycosides are considered.

  12. Production of polyclonal antibody against madecassoside and development of immunoassay methods for analysis of triterpene glycosides in Centella asiatica.

    Science.gov (United States)

    Tassanawat, Patcharin; Putalun, Waraporn; Yusakul, Gorawit; Sritularak, Boonchoo; Juengwatanatrakul, Thaweesak; Tanaka, Hiroyuki

    2013-01-01

    Centella asiatica (L.) Urban consists of two major triterpene glycosides, asiaticoside (AS) and madecassoside (MA), as active components used for wound healing and enhancing memory. To produce a polyclonal antibody against madecassoside (MA-PAb) and develop enzyme-linked immunosorbent assay (ELISA) and Eastern blotting methods for quantitative analysis of triterpene glycosides in Centella asiatica. An ELISA method was developed using polyclonal antibody against MA. An Eastern blotting method on the PES membrane was established for determination of MA and AS. The immunoassays were validated for sensitivity, precision, specificity and accuracy. The prepared MA-PAb shows specificity to MA and AS. The measuring range of triterpene glycosides was 0.39-50 µg/mL using the ELISA method. An Eastern blotting method was developed for determining individual MA and AS, which could be detected in the range of 62.5-500 ng. The limit of detection for MA and AS was 31.25 ng. The two methods developed showed good specificity, precision, and accuracy, and also correlated with high-performance liquid chromatography. These immunoassays have several advantages that include high sensitivity as well as being rapid and facile for determination of the triterpene glycosides in C. asiatica. Copyright © 2012 John Wiley & Sons, Ltd.

  13. Vibrational circular dichroism (VCD) studies on disaccharides in the CH region: toward discrimination of the glycosidic linkage position.

    Science.gov (United States)

    Taniguchi, Tohru; Monde, Kenji

    2007-04-07

    The structural features of carbohydrates are a combination of 1) sequence and types of mono-sugars, 2) stereochemistry of their glycosidic linkages, and 3) their glycosidic linkage sites. We performed the first systematic VCD study on glycoside linking site discrimination. VCD spectra, in the CH stretching region from 2000 to 4000 cm(-1), of eleven glucobioses (trehalose (alpha1-alpha1), neotrehalose (alpha1-beta1), isotrehalose (beta1-beta1), kojibiose (alpha1-2), nigerose (alpha1-3), maltose (alpha1-4), isomaltose (alpha1-6), sophorose (beta1-2), laminaribiose (beta1-3), cellobiose (beta1-4), gentiobiose (beta1-6)) suggested a possible new discrimination method for glyco analysis, while VCD spectra in the mid-IR region distinguished the stereochemistry (alpha or beta) of the glycosidic linkage. Both reducing and nonreducing glucobioses showed different VCD spectral features compared to their constituent D-glucose and the anomer-fixed model compounds. Interresidue interaction such as hydrogen bonding was suggested to cause these spectral differences. Interplay between residues is a common phenomenon and thus VCD analysis could be applicable to other di-, oligo- or poly-saccharides. Several isotropic labeled compounds were also measured to support spectral assignment and interpretation.

  14. Determination of flavonol glycosides in green tea, oolong tea and black tea by UHPLC compared to HPLC.

    Science.gov (United States)

    Jiang, Heyuan; Engelhardt, Ulrich H; Thräne, Claudia; Maiwald, Beate; Stark, Janina

    2015-09-15

    An UHPLC method for the determination of flavonol glycosides (FOG) from green and oolong tea vs. black tea has been developed for the first time. Sample clean-up method by means of polyamide column chromatography was optimized with multiple-step elution. Using UHPLC and HPLC with gradient elution and photodiode array detection, eighteen FOG compounds were determined with the aid of electrospray tandem mass spectrometry. These FOG compounds were qualified on both UHPLC and HPLC, and this UHPLC method successfully separated rutin (quercetin-3-O-rutinoside) and K-grg (kaempferol-3-O-glucorhamnoglucoside) while conventional HPLC method did not. The total amounts of FOG compounds in the tea samples were 2.32-5.67g/kg dry weight (calculated as aglycones), and there is no significant difference for the total FOG content among green tea, oolong tea and black tea. However, kaempferol glycosides are more abundant in green teas, while oolong tea has more quercetin and myricetin glycosides. In black tea quercetin glycosides were most abundant. Copyright © 2015 Elsevier Ltd. All rights reserved.

  15. A general approach to quantification of hydroxycinnamic acid derivatives and flavones, flavonols, and their glycosides by UV spectrophotometry

    Science.gov (United States)

    A general method was developed for the quantification of hydroxycinnamic acid derivatives and flavones, flavonols, and their glycosides based on the UV molar relative response factors (MRRF) of the standards. Each of these phenolic compounds contains a cinnamoyl structure and has a maximum absorban...

  16. Three unusual 22-beta-O-23-hydroxy-(5 alpha)-spirostanol glycosides from the fruits of Solanum torvum.

    Science.gov (United States)

    Iida, Yoshihiko; Yanai, Yoshihiro; Ono, Masateru; Ikeda, Tsuyoshi; Nohara, Toshihiro

    2005-09-01

    Three novel 22-beta-O-spirostanol oligoglycosides, torvosides J (1), K (2) and L (3) have been isolated from the fruits of Solanum torvum SWARTZ and their chemical structures have been characterized based on the spectroscopic means. They are worth of note as rare 22-beta-O-spirostanol glycosides.

  17. New aspects on the chemotaxonomy of Phytolacca dodecandra with regard to the isolation of phytolaccagenin, phytolaccagenic acid and their glycosides.

    Science.gov (United States)

    Spengel, S M; Luterbacher, S; Schaffner, W

    1995-08-01

    In leaves, roots and calli of P. dodecandra we found two 28,30-dicarboxyolean-12-enes and their glycosides in addition to the hitherto known four 28-monocarboxyolean-12-enes on which the chemotaxonomy was based. Therefore, P. dodecandra can no longer be considered as chemotaxonomically different from the other Phytolacca species.

  18. Identification and quantitation of glycosidically bound aroma compounds in three tobacco types by gas chromatography-mass spectrometry.

    Science.gov (United States)

    Cai, Kai; Xiang, Zhangmin; Pan, Wenjie; Zhao, Huina; Ren, Zhu; Lei, Bo; Geng, Zhaoliang

    2013-10-11

    Glycosidically bound aroma compounds in three different types of tobacco were investigated. After isolation of extracts obtained by Amberlite XAD-2 adsorption and ethyl acetate elution, glycosides were analyzed after enzymatic hydrolysis by gas chromatography-mass spectrometry (GC-MS) or directly after trifluoroacetylated (TFA) derivatization by GC-MS in electron ionization (EI) and negative chemical ionization (NCI) mode. In total 21 bound aglycones were identified by β-glucosidase hydrolysis. These aglycones mainly consisted of C13-norisoprenoids, aromatic components and sesquiterpenoids. Additionally, with the aid of enzymatic hydrolysis, 15 β-d-glucopyranosides and 1 β-d-rutinoside were tentatively identified by TFA derivatization. TFA method was validated by repeatability and successfully employed to analyze different types of tobacco. Principal component analysis (PCA) was carried out on identified glycoside variables to visualize the difference between the tobacco types and the relationship between the glycoside variables and the tobacco types was established. Copyright © 2013 Elsevier B.V. All rights reserved.

  19. Antioxidant efficacy of iridoid and phenylethanoid glycosides from the medicinal plant Teucrium chamaedris in cell-free systems.

    Science.gov (United States)

    Pacifico, Severina; D'Abrosca, Brigida; Pascarella, Maria Teresa; Letizia, Marianna; Uzzo, Piera; Piscopo, Vincenzo; Fiorentino, Antonio

    2009-09-01

    Twelve glycosides, seven iridoids and five phenylethanoids, have been isolated from leaf and root methanolic extracts of Wall Germander (Teucrium chamaedrys), a Mediterranean species historically used as a medicinal plant. Among them, three iridoid and one phenylethanoid glycosides have been isolated and characterized for the first time. All of the structures have been elucidated on the basis of their spectral data, especially 1D and 2D NMR experiments. The antioxidative properties of pure metabolites, as well as of crude organic extracts of the plant, have been analyzed on the basis of their DPPH radical scavenging capability. The antioxidant capacity in cell-free systems of the isolated metabolites was carried out by measuring their capabilities to inhibit the synthesis of thiobarbituric acid reactive species in assay media using as oxidable substrates a vegetable fat and the pentose sugar 2-deoxyribose and to prevent oxidative damage of the hydrosoluble bovine serum albumin (BSA) protein. Phenylethanoid glycosides resulted efficacious DPPH radical, while iridoid glycosides prevent massively the 2-deoxyribose and BSA oxidations in assay media.

  20. Stevia Glycosides : Chemical and Enzymatic Modifications of Their Carbohydrate Moieties to Improve the Sweet-Tasting Quality

    NARCIS (Netherlands)

    Gerwig, Gerrit J; Te Poele, Evelien M; Dijkhuizen, Lubbert; Kamerling, Johannis P

    2016-01-01

    Stevia glycosides, extracted from the leaves of the plant Stevia rebaudiana Bertoni, display an amazing high degree of sweetness. As processed plant products, they are considered as excellent bio-alternatives for sucrose and artificial sweeteners. Being noncaloric and having beneficial properties

  1. A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species

    DEFF Research Database (Denmark)

    Pičmanová, Martina; Neilson, Elizabeth H.; Motawia, Mohammed S.

    2015-01-01

    nitrogen at specific developmental stages. To investigate the presence of putative turnover products of cyanogenic glycosides, comparative metabolic profiling using LC-MS/MS and HR-MS complemented by ion-mobility mass spectrometry was carried out in three cyanogenic plant species: cassava, almond...

  2. Antioxidative properties of hydroxycinnamic acid derivatives and a phenylpropanoid glycoside. A pulse radiolysis study

    Energy Technology Data Exchange (ETDEWEB)

    Lin Weizhen; Yao Side; Lin Nianyun [Laboratory of Radiation Chemistry, Shanghai Institute of Nuclear Research, Academic Sinica, Shanghai (China); Navaratnam, Suppiah [Faculty of Science and Technology, North East Wales Institute of Higher Education, Mold Road, Plas Coch, Wraxham, Clwyd (United Kingdom)

    1998-10-01

    Spectral and redox properties of the phenoxyl radicals from hydroxycinnamic acid derivatives and one selected component of phenylpropanoid glycosides, verbascoside, were studied using pulse radiolysis techniques. On the basis of the pH dependence of phenoxyl radical absorptions, the pK{sub a} values for deprotonation of sinapic acid radical and ferulic acid radical are 4.9 and 5.2. The rate constants of one electron oxidation of those antioxidants by azide radical and bromide radical ion were determined at pH 7. The redox potentials of those antioxidants were determined as 0.59-0.71 V vs NHE at pH 7 with reference standard 4-methoxyphenol and resorcinol.

  3. Identification and quantification of glycoside flavonoids in the energy crop Albizia julibrissin

    Energy Technology Data Exchange (ETDEWEB)

    Lau, C.S.; Beitle, R.R.; Clausen, E.C. [University of Arkansas, Fayetteville (United States). Department of Chemical Engineering; Carrier, D.J. [University of Arkansas, Fayetteville (United States). Department of Biological and Agricultural Engineering; Bransby, D.I. [Auburn University, AL (United States). Department of Agronomy and Soils; Howard, L.R. [University of Arkansas, Fayetteville (United States). Department of Food Science; Lay, J.O. Jr.; Liyanage, R. [University of Arkansas, Fayetteville (United States). Department of Chemistry and Biochemistry

    2007-01-15

    Oxygen radical absorbance capacity (ORAC) values showed that methanolic extracts of Albizia julibrissin foliage displayed antioxidant activity. High performance liquid chromatography (HPLC) and mass spectrometry (MS) techniques were utilized in the identification of the compounds. The analysis conformed the presence of three compounds in A. julibrissin foliage methanolic extract: an unknown quercetin derivative with mass of 610 Da, hyperoside (quercetin-3-O-galactoside), and quercitrin quercetin-3-O-rhamnoside). Fast performance liquid chromatography (FPLC) was employed to fractionate the crude A. julibrissin foliage methanolic extract into its individual flavonoid components. The flavonoids were quantified in terms of mass and their respective contribution to the overall ORAC value. Quercetin glycosides accounted for 2.0% of total foliage. (author)

  4. Phenylpropanoid-substituted procyanidins and tentatively identified procyanidin glycosides from hawthorn (Crataegus spp.).

    Science.gov (United States)

    Sendker, Jandirk; Petereit, Frank; Lautenschläger, Marcus; Hellenbrand, Nils; Hensel, Andreas

    2013-01-01

    The rational use of hawthorn leafs and flowers from Crataegus spp. for declining cardiac performance is mainly due to flavon-C-glycosides and oligomeric procyanidins (OPC). From OPC-enriched extracts from different batches, a dimeric phenylpropanoid-substituted procyanidin (cinchonain II b, 1) was isolated and characterized by MS, CD, and NMR. Also the presence of higher oligomeric cinchonains (degree of polymerization 3 to 8) in hawthorn extracts was shown by a specific ultrahigh-pressure liquid chromatography-ESI-qTOF-MS method. Interestingly, strong evidence for the occurrence of oligomeric procyanidin hexosides was found by ultrahigh-pressure liquid chromatography-ESI-qTOF-MS analysis which additionally revealed the presence of peaks indicative of dimeric procyanidin hexosides by their exact mass, which were clearly distinguishable from the cinchonain II type peaks. Georg Thieme Verlag KG Stuttgart · New York.

  5. Steviol glycosides from Stevia: biosynthesis pathway review and their application in foods and medicine.

    Science.gov (United States)

    Yadav, Sudesh Kumar; Guleria, Praveen

    2012-01-01

    Stevia rebaudiana, a perennial herb from the Asteraceae family, is known to the scientific world for its sweetness and steviol glycosides (SGs). SGs are the secondary metabolites responsible for the sweetness of Stevia. They are synthesized by SG biosynthesis pathway operating in the leaves. Most of the genes encoding the enzymes of this pathway have been cloned and characterized from Stevia. Out of various SGs, stevioside and rebaudioside A are the major metabolites. SGs including stevioside have also been synthesized by enzymes and microbial agents. These are non-mutagenic, non-toxic, antimicrobial, and do not show any remarkable side-effects upon consumption. Stevioside has many medical applications and its role against diabetes is most important. SGs have made Stevia an important part of the medicinal world as well as the food and beverage industry. This article presents an overview on Stevia and the importance of SGs.

  6. New Ent-Kaurane-Type Diterpene Glycosides and Benzophenone from Ranunculus muricatus Linn.

    Directory of Open Access Journals (Sweden)

    Bi-Ling Wu

    2015-12-01

    Full Text Available Two new ent-kaurane diterpene glycosides, ranunculosides A (1 and B (2, and a new benzophenone, ranunculone C (3, were isolated from the aerial part of Ranunculus muricatus Linn. The chemical structures of compounds 1–3 were established to be (2S-ent-kauran-2β-ol-15-en-14-O-β-d-glucopyranoside, (2S,4S-ent-kauran-2β,18-diol-15-en-14-O-β-d-glucopyranoside, and (R-3-[2-(3,4-dihydroxybenzoyl-4,5-dihydroxy-phenyl]-2-hydroxylpropanoic acid, respectively, by spectroscopic data and chemical methods. The absolute configuration of 1 was determined by the combinational application of RP-HPLC analysis and Mosher’s method.

  7. A new C21 steroidal glycoside from Cynanchum inamoenum (Maxim.) Loes.

    Science.gov (United States)

    Wang, Li-Qin; Shen, Yue-Mao; Hu, Jiang-Miao; Zhou, Jun

    2008-01-01

    A new C21 steroidal glycoside, 5beta,6beta-epoxy-glaucogenin C-3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-d-glucopyranosyl-(1 --> 4)-beta-D-cymaropyranosyl-(1 --> 4)-beta-D-oleandropyranosyl-(1 --> 4)-beta-D-oleandropyranoside, named inamoside D (1), was isolated from the MeOH extract of the roots of Cynanchum inamoenum (Maxim.) Loes (Asclepiadaceae). In addition, five known compounds, including 7-demethoxytylophorine (2), dehydrodiconiferyl alcohol gamma'-O-beta-D-glucopyranoside (3), beta-d-fructofuranosyl-(2 --> 1)-alpha-D-(6-O-sinapoyl)-glucopyranoside (4), neohancoside C (5), and cuchiloside (6), have also been isolated. The structure of 1 was determined by 1D- and 2D-NMR spectroscopies. All the compounds were isolated from this plant for the first time.

  8. Immunopotentiation of Caffeoyl Glycoside from Picrorhiza scrophulariiflora on activation and cytokines secretion of immunocyte in vitro.

    Science.gov (United States)

    Zeng, Sheng; Wang, Dacheng; Cao, Yongguo; An, Na; Zeng, Fanqin; Han, Chuntian; Song, Yu; Deng, Xuming

    2008-12-10

    Many natural products have been used as immunomodulators either as immunosuppressants or immunostimulators. Recently, our lab has successfully isolated a 1,6-di-O-caffeoyl-beta-D-glucopyranoside, monomer named Caffeoyl Glycoside (CG) from the roots of Picrorhiza scrophulariiflora (Kutki). In the present study, we evaluated the effects of this compound on immunomodulation in vitro. Our results showed that CG stimulated cell proliferation of splenocytes and peritoneal macrophages, and enhanced the cytotoxicity of natural killer (NK) cells significantly. CG also increased CD4 and CD8 cell populations. Moreover, we found that CG has immunomodulatory activity by regulating expression of Th1 and Th2 related cytokines. Taken together, these results indicated that CG might have potential effects in regulating the immune system, and this compound might be a useful immunotherapeutic agent in treating various immunity-related diseases.

  9. A new antifungal phenolic glycoside derivative, iridoids and lignans from Alibertia sessilis (vell.) K. Schum. (Rubiaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Viviane C. da; Bolzani, Vanderlan da S.; Lopes, Marcia N. [UNESP, Araraquara, SP (Brazil). Inst. de Quimica. Dept. de Quimica Organica]. E-mail: mnlopes@iq.unesp.br; Young, Maria C.M. [Instituto de Botanica, Sao Paulo, SP (Brazil). Secao de Fisiologia e Bioquimica de Plantas

    2007-07-01

    A new antifungal phenolic glycoside, 3,4,5-trimethoxyphenyl-1-O-{beta}-D-(5-O-syringoyl)apiofuranosyl-(1 {yields} 6)-{beta}-D-glucopyranoside (1), together with four known iridoids, geniposidic acid (2), geniposide (3), 6{alpha}-hydroxygeniposide (4) and 6{beta}-hydroxygeniposide (5); two lignans, (+)-lyoniresinol-3{alpha}-O-{beta}-D-glucopyranoside (6), (-)-lyoniresinol-3{alpha}-O-{beta}-D-glucopyranoside (7); and two phenolic acids, chlorogenic (8) and salicylic acids (9) and D-manitol (10), were isolated from the ethanolic extract of the stems of Alibertia sessilis. Structures of 1 and of the known compounds were determined by spectroscopic analysis. All compounds isolated were evaluated for their antifungal activities against two phytopathogenic fungi strains Cladosporium cladosporioides and C. sphaerospermum by direct bioautography. (author)

  10. New flavonoid glycosides and other chemical constituents from Clerodendrum phlomidis leaves: isolation and characterisation.

    Science.gov (United States)

    Bharitkar, Yogesh P; Hazra, Abhijit; Shah, Siddharth; Saha, Sudeshna; Matoori, Anil Kumar; Mondal, Nirup B

    2015-01-01

    Phytochemical investigation of the plant Clerodendrum phlomidis Linn. F. (Lamiaceae) has now led to the isolation of two new flavonoid glycosides (1, 2) together with six known compounds identified as pectolinaringenin (3), pectolinaringenin-7-O-β-D-glucopyranoside (4), 24β-ethylcholesta-5,22E,25-triene-3β-ol (5), 24β-ethylcholesta-5,22E,25-triene-3β-O-β-D-glucopyranoside (6), (2S,3S,4R,10E)-2-[(2'R)-2'-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol (7) and andrographolide (8) mainly by spectroscopic analysis. Compounds 4 and 6-8 are reported for the first time from C. phlomidis.

  11. "Molecular trinity" for soft nanomaterials: Integrating nucleobases, amino acids, and glycosides to construct multifunctional hydrogelators.

    Science.gov (United States)

    Li, Xinming; Kuang, Yi; Xu, Bing

    2012-03-14

    This highlight introduces the development of hydrogelators consisting of nucleobases, amino acids, and glycosides (i.e., molecular trinity), or nucleobases and amino acids (i.e., nucleopeptides). These novel small molecule hydrogelators self-assemble in water to form stable supramolecular nanofibers/hydrogels and exhibit useful biological properties (e.g., biocompatibility, biostability, and the ability to bind and transport DNA into live cells). The approach discussed here not only provides a new strategy to develop soft biomaterials as a form of nanomedicines, but also contributes to the understanding of molecular self-assembly in water by modulating the non-covalent interactions derived from the three basic building blocks used in living organisms.

  12. Isolation and Characterization of Phenolic Glycoside from the Bark of Symplocos RacemosaRoxb

    Directory of Open Access Journals (Sweden)

    M. Vijayabaskaran

    2010-01-01

    Full Text Available A new phenolic glycoside, 3, 5 - dihydroxy - 2- (hydroxyl methyl - 6-(3,4,5-trimethoxy phenoxytetrahydro-2H-pyran-4-yl, 4-hydroxy-3-methoxy benzoate have been isolated from the dried bark of Symplocos racemosa. The structure was identified by extensive spectral analysis, especially FT-IR, GC-MS, 1H NMR and 13C NMR techniques. The method of isolation was simple, cost effective and efficient. The preliminary bioactivity of the compound was also evaluated. The ethanolic extract of Symplocos racemosa (EESR was investigated for its anti-pyretic activity against brewer’s yeast induced pyrexia. The antipyretic effect of EESR (measured as % reduction in body temperature was compared with paracetamol (100 mg/kg, orally. EESR in dose of 200 mg/kg caused significant decrease in body temperature of rats. This study has established the antipyretic activity of Symplocos racemosaand thus, justifies the ethnic uses of the plant.

  13. A glycoside hydrolase family 31 dextranase with high transglucosylation activity from Flavobacterium johnsoniae.

    Science.gov (United States)

    Gozu, Yoshifumi; Ishizaki, Yuichi; Hosoyama, Yuhei; Miyazaki, Takatsugu; Nishikawa, Atsushi; Tonozuka, Takashi

    2016-08-01

    Glycoside hydrolase family (GH) 31 enzymes exhibit various substrate specificities, although the majority of members are α-glucosidases. Here, we constructed a heterologous expression system of a GH31 enzyme, Fjoh_4430, from Flavobacterium johnsoniae NBRC 14942, using Escherichia coli, and characterized its enzymatic properties. The enzyme hydrolyzed dextran and pullulan to produce isomaltooligosaccharides and isopanose, respectively. When isomaltose was used as a substrate, the enzyme catalyzed disproportionation to form isomaltooligosaccharides. The enzyme also acted, albeit inefficiently, on p-nitrophenyl α-D-glucopyranoside, and p-nitrophenyl α-isomaltoside was the main product of the reaction. In contrast, Fjoh_4430 did not act on trehalose, kojibiose, nigerose, maltose, maltotriose, or soluble starch. The optimal pH and temperature were pH 6.0 and 60 °C, respectively. Our results indicate that Fjoh_4430 is a novel GH31 dextranase with high transglucosylation activity.

  14. LC/ESI-MS method applied to characterization of flavonoids glycosides in B. forficata subsp. pruinosa

    Directory of Open Access Journals (Sweden)

    Lidiane da Silveira Farias

    2014-06-01

    Full Text Available Bauhinia forficata is used in folk medicine for its hypoglycemiant effect. In the south of Brazil, the subspecies pruinosa is found in a region with the characteristic flora, pampa biome. This species has been consumed by the local population as a tea for diabetes treatment. We studied the chemical composition of hydroethanolic extracts using LC/ESI-MS. The leaf extracts were prepared by percolation with 50% (v/v ethanol. The chromatographic analyses were performed using a reverse-phase system, gradient elution with acetonitrile:phosphoric acid 0.05%, and ESI-MS in the positive ion mode. The chemical profile of the flavonoids was suggested to involve four quercetin and kaempferol glycosides.

  15. Anti-adipogenic chromone glycosides from Cnidium monnieri fruits in 3T3-L1 cells.

    Science.gov (United States)

    Kim, Seon Beom; Ahn, Jong Hoon; Han, Sang-Bae; Hwang, Bang Yeon; Kim, Sung Yeon; Lee, Mi Kyeong

    2012-10-01

    Seven new chromone glycosides, monnierisides A (3), B (10), C (11), D (12), E (13), F (15) and G (16) were isolated from Cnidium. monnieri, together with ten known chromone derivatives, undulatoside A (1), cnidimol C (2), saikochromoside A (4), cnidimoside A (5), cnidimoside B (6), 2-methyl-5-hydroxy-6-(2-butenyl-3-hydroxymethyl)-7-(β-d-glucopyranosyloxy)-4H-1-benzopyran-4-one (7), cnidimol D (8), hydroxycnidimoside A (9), umtatin (14) and 6'-hydroxylangelicain (17). The structures of isolated compounds were determined on the basis of spectroscopic analysis including 1D, 2D NMR and HR-MS. Among the compounds isolated, compounds 5, 6, 9 and 10 significantly inhibited adipocyte differentiation as measured by fat accumulation in 3T3-L1 cells using Oil Red O staining. Copyright © 2012 Elsevier Ltd. All rights reserved.

  16. Stereoselective C-glycosidation of D-fucose derivatives directed by the protective groups.

    Science.gov (United States)

    Cortezano-Arellano, Omar; Meléndez-Becerra, Camilo A; Cortés, Fernando; Sartillo-Piscil, Fernando; Cordero-Vargas, Alejandro

    2014-07-01

    Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishi's method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (α anomer), in which the stereoselective outcome is in apparent concordance with Woerpel's model. On the other hand, their benzylated congeners produce the 1,3-cis products (β anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones. Copyright © 2014 Elsevier Ltd. All rights reserved.

  17. Evaluation of a silicon oxynitride hydrophilic interaction liquid chromatography column in saccharide and glycoside separations.

    Science.gov (United States)

    Wan, Huihui; Sheng, Qianying; Zhong, Hongmin; Guo, Xiujie; Fu, Qing; Liu, Yanfang; Xue, Xingya; Liang, Xinmiao

    2015-05-01

    The retention characteristics of a silicon oxynitride stationary phase for carbohydrate separation were studied in hydrophilic interaction chromatography mode. Four saccharides including mono-, di-, and trisaccharides were employed to investigate the effects of water content and buffer concentration in the mobile phase on hydrophilic interaction liquid chromatography retention. For the tested saccharides, the silicon oxynitride column demonstrated excellent performance in terms of separation efficiency, hydrophilicity, and interesting separation selectivity for carbohydrates compared to the bare silica stationary phase. Finally, the silicon oxynitride hydrophilic interaction liquid chromatography column was employed in the separation of complex samples of fructooligosaccharides, saponins, and steviol glycoside from natural products. The resulting chromatograms demonstrated good separation efficiency and longer retention compared with silica, which further confirmed the advantages and potential application of silicon oxynitride stationary phase for hydrophilic interaction liquid chromatography separation. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  18. Structure elucidation of new oleanane-type glycosides from three species of Acanthophyllum.

    Science.gov (United States)

    Timité, Gaoussou; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Ramezani, Mohammad; Rustaiyan, Abdolhossein; Mirjolet, Jean-François; Duchamp, Olivier; Lacaille-Dubois, Marie-Aleth

    2010-05-01

    From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (1) and gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT-29 and HCT 116). Copyright 2010 John Wiley & Sons, Ltd.

  19. Four new steroidal glycosides from Solanum torvum and their cytotoxic activities.

    Science.gov (United States)

    Lu, Yuanyuan; Luo, Jianguang; Huang, Xuefeng; Kong, Lingyi

    2009-01-01

    Two novel C-22 steroidal lactone saponins, namely solanolactosides A, B (1, 2) and two new spirostanol glycosides, namely torvosides M, N (3, 4) were isolated from ethanol extract of aerial parts of Solanum torvum. Their structures were characterized as solanolide 6-O-[alpha-l-rhamnopyranosyl-(1-->3)-O-beta-d-quinovopyranoside] (1), solanolide 6-O-[beta-d-xylopyranosyl-(1-->3)-O-beta-d-quinovopyranoside] (2), yamogenin 3-O-[beta-d-glucopyranosyl-(1-->6)-O-beta-d-glucopyranoside] (3) and neochlorogenin 3-O-[beta-d-glucopyranosyl-(1-->6)-O-beta-d-glucopyranoside] (4) on the basis of spectroscopic analysis. The cytotoxicities of the saponins (1-4) were evaluated in vitro against a panel of human cancer cell lines. Compounds 3 and 4 showed significant cytotoxic activity with the cell lines.

  20. Steady state kinetic analysis of substrate specificity of glycoside hydrolases from families 13 and 38

    DEFF Research Database (Denmark)

    Nielsen, Jonas Willum

    Glycosidases are widespread in nature, where they perform a diverse range of functions. The glycoside hydrolase (GH) family 38, α-mannosidase II enzymes play a crucial role in mammalian cells, in the maturation of N-glycosylated proteins in the Golgi apparatus and in catabolism in cytosol...... been identified in various enzymes, often based on crystal structures, and only few have been characterized in terms of structure-function relationship. Together SBS1 and SBS2 of barley α-amylase isozyme 1 probably represent the two most extensively studied SBSs. SBS2, largely governed by Tyr380, has...... been shown to be important for AMY1 adhesion to starch granules, but seems to play no significant role in the degradation of oligosaccharides, and only a minor role in the degradation of amylose. In Manuscript 2, a steady state kinetic analysis of amylopectin depolymerization by AMY1 and the SBS2...

  1. Isocoumarin derivatives and monoterpene glycoside from the seeds of Orychophragmus violaceus.

    Science.gov (United States)

    Zhang, Guang-Jie; Li, Bin; Chen, Li; Tian, Ying; Liu, Shi-Jun; Cui, Hui-Min; Dong, Jun-Xing

    2018-03-01

    Five new compounds, including four new isocoumarin derivatives [orychophramarin A-D (1-4)] and a new monoterpene glycoside [orychovioside A (5)], together with fourteen known compounds were isolated from the seeds of Orychophragmus violaceus. Their structures were established on the basis of chemical evidence and spectroscopic analysis. Compound 1 showed significant cytotoxicity against HCT-116 and Hela cell lines compared with the positive control group (Cisplatin) with IC 50 values of 5.10 and 8.91μM, respectively. Compound 1 exhibited evident cell cycle retardation that arrested HCT-116 cells at G 2 phase and induced apoptosis in HCT-116 cells in the further mechanism study. Copyright © 2017 Elsevier B.V. All rights reserved.

  2. Syntheses of alpha-arbutin-alpha-glycosides and their inhibitory effects on human tyrosinase.

    Science.gov (United States)

    Sugimoto, Kazuhisa; Nomura, Koji; Nishimura, Takahisa; Kiso, Taro; Sugimoto, Kenji; Kuriki, Takashi

    2005-03-01

    Alpha-arbutin is a tyrosinase inhibitor. We synthesized alpha-arbutin-alpha-glycosides by the transglycosylation reaction of cyclomaltodextrin glucanotransferase from Bacillus macerans using alpha-arbutin and starch as acceptor and donor molecules, respectively. We isolated and characterized two major products from the reaction mixture. The structural analyses using 13C- and 1H-NMR spectroscopy proved that they were 4-hydroxyphenyl alpha-maltoside (alpha-Ab-alpha-G1) and 4-hydroxyphenyl alpha-maltotrioside (alpha-Ab-alpha-G2). Both alpha-Ab-alpha-G1 and alpha-Ab-alpha-G2 exhibited competitive-type inhibition on human tyrosinase as alpha-arbutin does. Their K(i) values were calculated to be 0.6 mM and 2.8 mM, respectively, which is slightly and significantly higher than that of alpha-arbutin (0.2 mM).

  3. Cyprotuoside C and cyprotuoside D, two new cycloartane glycosides from the rhizomes of Cyperus rotundus.

    Science.gov (United States)

    Lin, San-Qing; Zhou, Zhong-Liu; Li, Chun-Yan

    2017-11-09

    Cyprotuoside C (1) and cyprotuoside D (2), two new cycloartane glycosides were isolated from the ethanol extract of the rhizomes of Cyperus rotundus. Their structures were identified as 24R-9, 10-seco-cycloartan-1 (10), 9 (11)-dien-3β, 7β, 24, 25-tetraol 3-O-β-D-xylopyranosyl-(1→4)-[α-L-arabinopyranosyl-(1→6)]-β-D-glucopyranosyl-25-O-β-D-glucuronide (1) and 9, 10-seco-cycloartan-1 (10), 9 (11), 23 (24)-trien-3β, 7β, 25-triol 3-O-β-D-xylopyranosyl-(1→4)-{α-L-arabinopyranosyl-(1→6)-[ α-L-rhamnopyranosyl-(1→2)-]}-β-D-glucopyranosyl-25-O-β-D-glucuronide (2) by spectroscopic methods.

  4. Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine

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    Jan Duchek

    2013-04-01

    Full Text Available The synthesis of stable guanofosfocin analogues has attracted considerable attention in the past 15 years. Several guanofosfocin analogues mimicking the three constitutional elements of mannose, ribose, and guanine were designed and synthesized. Interest in ether-linked pseudodisaccharides and 8-alkylated guanines is increasing, due to their potential applications in life science. In this article, a novel guanofosfocin analogue 6, an ether-linked pseudodisaccharide connected α-C-glycosidically to an 8-alkylated guanine, was synthesized in a 10-longest linear step sequence from known diol 13, resulting in an overall yield of 26%. The key steps involve the ring-opening of cyclic sulfate 8 by alkoxide generated from 7 and a reductive cyclization of 4-N-acyl-2,4-diamino-5-nitrosopyrimidine 19 to form compound 6.

  5. Bioactive Flavone-C-Glycosides of the African Medicinal Plant Biophytum umbraculum

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    Helle Wangensteen

    2013-08-01

    Full Text Available Three flavone-C-glycosides—cassiaoccidentalin A (1, isovitexin (2 and isoorientin (3—were isolated from the ethyl acetate (EtOAc soluble fraction of the methanol crude extract of the African medicinal plant Biophytum umbraculum, This is the first report of these compounds in this plant. All compounds were identified by spectroscopic analysis and comparison with published data. Isoorientin (3 and the EtOAc extract showed the greatest antioxidant activity in the DPPH assay as well as the strongest inhibition of xanthine oxidase (XO and 15-lipoxygenase (15-LO. From these results, the extract of B. umbraculum might be a valuable source of flavone C-glycosides.

  6. Synthesis of nonionic surfactants with azole ring bearing N-glycosides and their antibacterial activity

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    Fawzia Taieb Brahimi

    2017-05-01

    Full Text Available Six azoles with n-pentyl side chain 6–9, 11 and 12 were synthesized from n-hexanoic acid. Three N-glycosides namely: 5-pentyl-2-(d-amino arabinoside-1,3,4-oxadiazole (13, 5-pentyl-2-(d-aminoglycoside-1,3,4-thiadiazole (14, and 3-pentyl-4-(d-amino xyloside-4H-1,2,4-triazole-5-thiol (15 were prepared from already synthesized n-pentyl azoles 6, 7 and 11, respectively. Surface activity properties of water soluble synthesized compounds 6, 7, and 11–15 were studied in terms of surface tension, cloud point and critical micelle concentration. The antibacterial activities were assessed using the paper disk diffusion and broth dilution methods against gram-positive and gram-negative bacteria. Some of the synthetic compounds showed promising activity against microorganisms under test in comparison to commercially available antibiotics polymixine and oxytetracycline.

  7. Perillanolides A and B, new monoterpene glycosides from the leaves of Perilla frutescens

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    Yang Liu

    Full Text Available Abstract Two new monoterpene glycosides, perillanolides A and B, together with a known compound reported from the genus Perilla for the first time were isolated and characterized from the leaves of Perilla frutescens (L. Britton, Lamiaceae, a garnish and colorant for foods as well as commonly used for traditional medicine. The structures of the isolated compounds were elucidated on the basis of extensive spectroscopic evidences derived from nuclear magnetic resonance experiments, mass spectrometry and by comparing their physical and spectroscopic data of literature. These compounds, together with the previously isolated secondary metabolites of this species, were investigated for their inhibitory effects on xanthine oxidase in vitro. Of the compounds, luteolin showed the strongest inhibitory activity with an IC50 value of 2.18 µM. Esculetin and scutellarein moderately inhibited the enzyme, while perillanolides A and B, and 4-(3,4-dihydroxybenzoyloxymethylphenyl-O-β-D-glucopyranoside exerted weak activities.

  8. Free-radical Scavenging Flavonol 3-O-glycosides from the Leaves of Ribes biebersteinii Berl.

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    Abbas Delazar

    2010-04-01

    Full Text Available Ribes biebersteinii Berl. (Grossulariaceae, commonly known as ‘reddish-black berry’, is an Iranian medicinal plant found mainly in the region of the Arasbaran forests in Iran. Reversed-phase preparative HPLC analyses of the methanol extract of the leaves of this plant afforded four flavonol glycosides, e.g. quercetin 3-O-sophoroside (1, quercetin 3-O-sambubioside (2, kaempferol 3-O-sophoroside (3 and kaempferol 3,5-di-O-b-D-glucopyranoside (4. The free-radical-scavenging properties of the n-hexane, DCM and MeOH extracts, as well as the isolated compounds 1-4 were evaluated by the 2,2-diphenyl-1-picryl-hydrazyl (DPPH assay. Keywords:Ribes biebersteinii Berl.; Grossulariaceae; free-radical

  9. Enzymatic production of highly soluble myricitrin glycosides using beta-galactosidase.

    Science.gov (United States)

    Shimizu, Ryosuke; Shimabayashi, Hiroshi; Moriwaki, Masamitsu

    2006-04-01

    Myricitrin, a botanical flavonol glycoside, could be a useful ingredient of functional foods, cosmetics, and medicines because of its high anti-oxidative activity. However, due to its insolubility in water, it has a limited range of use. To improve this solubility, we glycosylated myricitrin by an enzymatic transglycosylate reaction. Myricitrin was galactosylated by beta-galactosidase from Bacillus circulans using lactose as a sugar donor. The reaction product was 480 times more soluble than myricitrin. Four myricitrin galactosides were isolated from the reaction products by column chromatography, and their molecular structures were identified by using ESI-MS, 1H-NMR, 13C-NMR, 1H-1H COSY, 1H-13C HMQC and 1H-13C HMBC analysis. The solubility of these four myricitrin galactosides was more than 3.9 x 10(3) fold that of myricitrin, and each had similar anti-oxidative activity to that of myricitrin.

  10. Use of nanostructure initiator mass spectrometry (NIMS to deduce selectivity of reaction in glycoside hydrolases

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    Kai eDeng

    2015-10-01

    Full Text Available Chemically synthesized nanostructure-initiator mass spectrometry (NIMS probes derivatized with tetrasaccharides were used to study the reactivity of representative Clostridium thermocellum β-glucosidase, endoglucanases and cellobiohydrolase. Diagnostic patterns for reactions of these different classes of enzymes were observed. Results show sequential removal of glucose by the β-glucosidase and a progressive increase in specificity of reaction from endoglucanases to cellobiohydrolase. Time-dependent reactions of these polysaccharide-selective enzymes were modeled by numerical integration, which provides a quantitative basis to make functional distinctions among a continuum of naturally evolved catalytic properties. Consequently, our method, which combines automated protein translation with high-sensitivity and time-dependent detection of multiple products, provides a new approach to annotate glycoside hydrolase phylogenetic trees with functional measurements.

  11. Synthesis of novel bioactive lactose-derived oligosaccharides by microbial glycoside hydrolases

    Science.gov (United States)

    Díez-Municio, Marina; Herrero, Miguel; Olano, Agustín; Moreno, F Javier

    2014-01-01

    Prebiotic oligosaccharides are increasingly demanded within the Food Science domain because of the interesting healthy properties that these compounds may induce to the organism, thanks to their beneficial intestinal microbiota growth promotion ability. In this regard, the development of new efficient, convenient and affordable methods to obtain this class of compounds might expand even further their use as functional ingredients. This review presents an overview on the most recent interesting approaches to synthesize lactose-derived oligosaccharides with potential prebiotic activity paying special focus on the microbial glycoside hydrolases that can be effectively employed to obtain these prebiotic compounds. The most notable advantages of using lactose-derived carbohydrates such as lactosucrose, galactooligosaccharides from lactulose, lactulosucrose and 2-α-glucosyl-lactose are also described and commented. PMID:24690139

  12. New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects.

    Science.gov (United States)

    Abdel Bar, Fatma M

    2015-01-01

    A new chalcanonol glycoside dimer, bis-O-[(I-4') → (II-6')]-α-hydroxyphloretin-2'-O-β-glucoside (1), in addition to six known compounds, namely (-)-epicatechin (2) and (-)-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2'-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.

  13. Glycosides of benzodioxole-indole alkaloids from Narcissus having axial chirality.

    Science.gov (United States)

    Rezanka, Tomás; Rezanka, Pavel; Sigler, Karel

    2010-02-01

    Glycosides of benzodioxole-indole alkaloid 6-hydroxy-galanthindole (7-(6'-(hydroxymethyl)benzo[d][1',3']dioxol-5'-yl)-1-methyl-1H-indol-6-ol) having axial chirality were isolated from Narcissus cultivar 'Dutch Master'. The structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, CD, MS, 1D and 2D NMR spectra, and computational chiroptical methods. The aglycone has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis and is connected to a saccharide moiety linked at C-6 and made up of one, two, or three sugars (glucose, alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranose, and trisaccharide ([beta-D-xylopyranosyl(1-->2)]-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranose). 2009 Elsevier Ltd. All rights reserved.

  14. Steroidal glycosides from the leaves of Ruscus colchicus: isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling.

    Science.gov (United States)

    Perrone, Angela; Muzashvili, Tamara; Napolitano, Assunta; Skhirtladze, Alexandre; Kemertelidze, Ether; Pizza, Cosimo; Piacente, Sonia

    2009-12-01

    An HPLC-ESIMS(n) method, based on high-performance liquid chromatography coupled to electrospray positive ionisation multistage ion trap mass spectrometry, has been used as an effective tool to rapidly identify and guide the isolation of target saponins from the ethanol extract of the leaves of Ruscus colchicus Y. Yeo. Twenty-two steroidal glycosides, including seventeen furostanol, four spirostanol and one cholestane glycosides, were online identified. Subsequently, compounds were isolated and their structures were established by the extensive use of 1D- and 2D-NMR experiments. The structures identified by MS were fully consistent with those elucidated by NMR data. Sixteen steroidal glycosides, including thirteen furostanol, two spirostanol and one cholestane glycosides, were identified along with four known furostanol and two spirostanol glycosides. The saponin profile shows that the furostanol glycosides are the main constituents of R. colchicus extract, unlike the other Ruscus species, for which the spirostanol derivatives generally are reported as the major compounds. Moreover, for the first time a cholestane glycoside has been isolated from R. colchicus.

  15. The role of fluorescence polarization immuno-assay in the diagnosis of plant-induced cardiac glycoside poisoning livestock in South Africa

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    R.A. Schultz

    2005-09-01

    Full Text Available Poisoning with cardiac glycoside-containing plants is collectively the most important plant-associated poisoning of livestock in southern Africa. As a diagnosis of this significant poisoning is currently based on circumstantial evidence, a practical chemical procedure indicating the presence of cardiac glycosides in plants and animal specimens would be of considerable benefit. The fluorescence polarization immunoassay (FPIA method, used to determine digoxin plasma levels in humans and dogs, was adapted to estimate cardiac glycoside levels in known cardiac-glycoside- containing plants as well as in the rumen and organs of dosed sheep. Positive FPIA values were obtained with bufadienolide-containing plants, while negative results were obtained with plants not known to contain cardiac glycosides. The FPIA has aided in the diagnosis of cardiac glycoside poisoning in livestock and game in 30 outbreaks examined at the Division of Toxicology, Onderstepoort Veterinary Institute. Each outbreak is briefly described. As a result of this assay, a better understanding of cardiac glycoside poisoning has been reached.

  16. Structural relationships in the lysozyme superfamily: significant evidence for glycoside hydrolase signature motifs.

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    Alexandre Wohlkönig

    Full Text Available BACKGROUND: Chitin is a polysaccharide that forms the hard, outer shell of arthropods and the cell walls of fungi and some algae. Peptidoglycan is a polymer of sugars and amino acids constituting the cell walls of most bacteria. Enzymes that are able to hydrolyze these cell membrane polymers generally play important roles for protecting plants and animals against infection with insects and pathogens. A particular group of such glycoside hydrolase enzymes share some common features in their three-dimensional structure and in their molecular mechanism, forming the lysozyme superfamily. RESULTS: Besides having a similar fold, all known catalytic domains of glycoside hydrolase proteins of lysozyme superfamily (families and subfamilies GH19, GH22, GH23, GH24 and GH46 share in common two structural elements: the central helix of the all-α domain, which invariably contains the catalytic glutamate residue acting as general-acid catalyst, and a β-hairpin pointed towards the substrate binding cleft. The invariant β-hairpin structure is interestingly found to display the highest amino acid conservation in aligned sequences of a given family, thereby allowing to define signature motifs for each GH family. Most of such signature motifs are found to have promising performances for searching sequence databases. Our structural analysis further indicates that the GH motifs participate in enzymatic catalysis essentially by containing the catalytic water positioning residue of inverting mechanism. CONCLUSIONS: The seven families and subfamilies of the lysozyme superfamily all have in common a β-hairpin structure which displays a family-specific sequence motif. These GH β-hairpin motifs contain potentially important residues for the catalytic activity, thereby suggesting the participation of the GH motif to catalysis and also revealing a common catalytic scheme utilized by enzymes of the lysozyme superfamily.

  17. HPLC-MSn identification and quantification of flavonol glycosides in 28 wild and cultivated berry species.

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    Mikulic-Petkovsek, Maja; Slatnar, Ana; Stampar, Franci; Veberic, Robert

    2012-12-15

    Berries and red fruits are rich dietary sources of polyphenols with reported health benefits. More than 50 different flavonols (glycosides of quercetin, myricetin, kaempferol, isorhamnetin, syringetin and laricitrin) have been detected and quantified with HPLC-MS(n) in fruits of blueberry, bilberry, cranberry, lingonberry, eastern shadbush, Japanese wineberry, black mulberry, chokeberry, red, black and white currants, jostaberry, red and white gooseberry, hardy kiwifruit, goji berry, rowan, dog rose, Chinese and midland hawthorn, wild and cultivated species of blackberry, raspberry, strawberry and elderberry. The phenolic constituents and contents varied considerably among the analyzed berry species. Elderberry contained the highest amount of total flavonols (450-568 mgkg(-1) FW), followed by berry species, containing more than 200 mgkg(-1) FW of total: chokeberry (267mgkg(-1)), eastern shadbush (261 mgkg(-1)), wild grown blackberry (260 mgkg(-1)), rowanberry (232 mgkg(-1)), american cranberry (213 mgkg(-1)) and blackcurrants (204 mgkg(-1)). Strawberry (10.5 mgkg(-1)) and white currants (4.5 mgkg(-1)) contained the lowest amount of total flavonols. Quercetins represent the highest percentage (46-100%) among flavonols in most analyzed berries. In wild strawberry and gooseberry the prevailing flavonols belong to the group of isorhamnetins (50-62%) and kaempferols, which represent the major part of flavonols in currants (49-66%). Myricetin glycosides could only be detected in chokeberry, rowanberry and species from the Grossulariaceae, and Adoxaceae family and Vaccinium genus. Wild strawberry and blackberry contained from 3- to 5-fold higher total flavonols than the cultivated one. Copyright © 2012 Elsevier Ltd. All rights reserved.

  18. Effect of microwave heating on content of cyanogenic glycosides in linseed

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    Ivanov Dušica

    2012-01-01

    Full Text Available Linseed is a good source of linoleic (LA, 18:2, n-6 and especially α-linolenic acid (ALA, 18:3, n-3, ω6 and ω-3 polyunsaturated fatty acids (PUFA, which are essential because mammals, and therefore humans, cannot endogenously synthesize them and must adopt them exogenously from dietary sources. In spite of its high nutritive value, linseed has not been effectively exploited in animal feeding, due to the fact that it contains antinutritive components, which are cyanogenic glycosides (CG and antivitamin B6 (linatine. CGs are a major limitation in application of linseed and its meal in animal nutrition. The objective of the study was to investigate effect of microwave heat treatment on the content of hydrogen cyanide, and consequently cyanogenic glycosides in linseed. Operating frequency of microwave oven was 2450 mHz, and working power was 240W, 400W, 560W and 800W. Samples were treated for 0, 3, 6 and 10 minutes for every working power. When microwave power of 560 W and 800 W was used for 6 min and longer, linseed samples were burned and damaged, therefore these treatments should not be used. Minimal time of heating with microwave power of 400W, which would provide reduction of HCN content under allowed limits (250 mg/kg of linseed, was determined graphically using three-dimensional contour plot graph and it was 290 s (4 minutes and 50 s. This regime is recommended for treating linseed before usage as a feed compound.

  19. Exploring glycoside hydrolases and accessory proteins from wood decay fungi to enhance sugarcane bagasse saccharification.

    Science.gov (United States)

    Valadares, Fernanda; Gonçalves, Thiago A; Gonçalves, Dayelle S P O; Segato, Fernando; Romanel, Elisson; Milagres, Adriane M F; Squina, Fabio M; Ferraz, André

    2016-01-01

    Glycoside hydrolases (GHs) and accessory proteins are key components for efficient and cost-effective enzymatic hydrolysis of polysaccharides in modern, biochemically based biorefineries. Currently, commercialized GHs and accessory proteins are produced by ascomycetes. However, the role of wood decay basidiomycetes proteins in biomass saccharification has not been extensively pursued. Wood decay fungi degrade polysaccharides in highly lignified tissues in natural environments, and are a promising enzyme source for improving enzymatic cocktails that are designed for in vitro lignocellulose conversion. GHs and accessory proteins were produced by representative brown- and white-rot fungi, Laetiporus sulphureus and Pleurotus ostreatus, respectively. Concentrated protein extracts were then used to amend commercial enzymatic cocktails for saccharification of alkaline-sulfite pretreated sugarcane bagasse. The main enzymatic activities found in the wood decay fungal protein extracts were attributed to endoglucanases, xylanases and β-glucosidases. Cellobiohydrolase (CBH) activities in the L. sulphureus and P. ostreatus extracts were low and nonexistent, respectively. The initial glucan conversion rates were boosted when the wood decay fungal proteins were used to replace half of the enzymes from the commercial cocktails. L. sulphureus proteins increased the glucan conversion levels, with values above those observed for the full load of commercial enzymes. Wood decay fungal proteins also enhanced the xylan conversion efficiency due to their high xylanase activities. Proteomic studies revealed 104 and 45 different proteins in the P. ostreatus and L. sulphureus extracts, respectively. The enhancement of the saccharification of alkaline-pretreated substrates by the modified enzymatic cocktails was attributed to the following protein families: GH5- and GH45-endoglucanases, GH3-β-glucosidases, and GH10-xylanases. The extracellular proteins produced by wood decay fungi provide

  20. Construction of a rice glycoside hydrolase phylogenomic database and identification of targets for biofuel research

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    Rita eSharma

    2013-08-01

    Full Text Available Glycoside hydrolases (GH catalyze the hydrolysis of glycosidic bonds in cell wall polymers and can have major effects on cell wall architecture. Taking advantage of the massive datasets available in public databases, we have constructed a rice phylogenomic database of GHs (http://ricephylogenomics.ucdavis.edu/cellwalls/gh/. This database integrates multiple data types including the structural features, orthologous relationships, mutant availability and gene expression patterns for each GH family in a phylogenomic context. The rice genome encodes 437 GH genes classified into 34 families. Based on pairwise comparison with eight dicot and four monocot genomes, we identified 138 GH genes that are highly diverged between monocots and dicots, 57 of which have diverged further in rice as compared with four monocot genomes scanned in this study. Chromosomal localization and expression analysis suggest a role for both whole-genome and localized gene duplications in expansion and diversification of GH families in rice. We examined the meta-profiles of expression patterns of GH genes in twenty different anatomical tissues of rice. Transcripts of 51 genes exhibit tissue or developmental stage-preferential expression, whereas, seventeen other genes preferentially accumulate in actively growing tissues. When queried in RiceNet, a probabilistic functional gene network that facilitates functional gene predictions, nine out of seventeen genes form a regulatory network with the well-characterized genes involved in biosynthesis of cell wall polymers including cellulose synthase and cellulose synthase-like genes of rice. Two-thirds of the GH genes in rice are up regulated in response to biotic and abiotic stress treatments indicating a role in stress adaptation. Our analyses identify potential GH targets for cell wall modification.