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Sample records for peony glycosides reverses

  1. Reverse transcriptase domain sequences from tree peony (Paeonia suffruticosa) long terminal repeat retrotransposons: sequence characterization and phylogenetic analysis

    PubMed Central

    Guo, Da-Long; Hou, Xiao-Gai; Jia, Tian

    2014-01-01

    Tree peony is an important horticultural plant worldwide of great ornamental and medicinal value. Long terminal repeat retrotransposons (LTR-retrotransposons) are the major components of most plant genomes and can substantially impact the genome in many ways. It is therefore crucial to understand their sequence characteristics, genetic distribution and transcriptional activity; however, no information about them is available in tree peony. Ty1-copia-like reverse transcriptase sequences were amplified from tree peony genomic DNA by polymerase chain reaction (PCR) with degenerate oligonucleotide primers corresponding to highly conserved domains of the Ty1-copia-like retrotransposons in this study. PCR fragments of roughly 270bp were isolated and cloned, and 33 sequences were obtained. According to alignment and phylogenetic analysis, all sequences were divided into six families. The observed difference in the degree of nucleotide sequence similarity is an indication for high level of sequence heterogeneity among these clones. Most of these sequences have a frame shift, a stop codon, or both. Dot-blot analysis revealed distribution of these sequences in all the studied tree peony species. However, different hybridization signals were detected among them, which is in agreement with previous systematics studies. Reverse transcriptase PCR (RT-PCR) indicated that Ty1-copia retrotransposons in tree peony were transcriptionally inactive. The results provide basic genetic and evolutionary information of tree peony genome, and will provide valuable information for the further utilization of retrotransposons in tree peony. PMID:26019529

  2. Microsatellite marker development in peony using next generation sequencing

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Peonies (Paeonia), the grand garden perennial of spring and early summer, are economically important to the international cut flower market. Herbaceous peonies (Paeonia section Paeonia), tree peonies (Paeonia section Moutan), and intersectional crosses between the two types (Itoh Paeonia hybrids) ...

  3. What secrets lurk in peony DNA?

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The scientists at USDA ARS National Clonal Germplasm Repository and the USDA ARS Arctic and Subarctic Plant Gene Bank have begun to collect and research peonies (Paeonia L). These scientists were able to isolate DNA from dormant buds as well as leaves of peonies. They are working with other scientis...

  4. Diversity of arthropod pests from high latitude peony production

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Peony (Paeonia spp.) is a fairly new crop to Alaska. Alaska has a late season with peony harvests into July-August when peony flowers are not readily available on the world markets. The University of Alaska Fairbanks has developed a production package to include variety performance, panting time, ha...

  5. 'Peony Nebula' Star Settles for Silver Medal

    NASA Technical Reports Server (NTRS)

    2008-01-01

    [figure removed for brevity, see original site] [figure removed for brevity, see original site] Poster Version Movie

    If our galaxy, the Milky Way, were to host its own version of the Olympics, the title for the brightest known star would go to a massive star called Eta Carina. However, a new runner-up now the second-brightest star in our galaxy has been discovered in the galaxy's dusty and frenzied interior. This image from NASA's Spitzer Space Telescope shows the new silver medalist, circled in the inset above, in the central region of our Milky Way.

    Dubbed the 'Peony nebula' star, this blazing ball of gas shines with the equivalent light of 3.2 million suns. The reigning champ, Eta Carina, produces the equivalent of 4.7 million suns worth of light though astronomers say these estimates are uncertain, and it's possible that the Peony nebula star could be even brighter than Eta Carina.

    If the Peony star is so bright, why doesn't it stand out more in this view? The answer is dust. This star is located in a very dusty region jam packed with stars. In fact, there could be other super bright stars still hidden deep in the stellar crowd. Spitzer's infrared eyes allowed it to pierce the dust and assess the Peony nebula star's true brightness. Likewise, infrared data from the European Southern Observatory's New Technology Telescope in Chile were integral in calculating the Peony nebula star's luminosity.

    The Peony nebula, which surrounds the Peony nebular star, is the reddish cloud of dust in and around the white circle.

    The movie begins by showing a stretch of the dusty and frenzied central region of our Milky Way galaxy. It then zooms in to reveal the 'Peony nebula' star the new second-brightest star in the Milky Way, discovered in part by NASA's Spitzer Space Telescope.

    This is a three-color composite showing infrared observations from two Spitzer instruments. Blue represents 3.6-micron light and green shows light of 8 microns, both captured by Spitzer's infrared array camera. Red is 24-micron light detected by Spitzer's multiband imaging photometer.

  6. First Report of Tobacco Rattle Virus in Peony in Alaska

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In 2007, scattered peony (Paeonia lactiflora ‘Sarah Bernhardt’) plants cultivated on plots at the University of Alaska Experimental Station in Fairbanks, Alaska, contained distinct leaf ringspot patterns. Leaf samples from symptomatic plants were collected in early July (6 plants) and late September...

  7. Preparation and chromatographic evaluation of a newly designed steviol glycoside modified-silica stationary phase in hydrophilic interaction liquid chromatography and reversed phase liquid chromatography.

    PubMed

    Liang, Tu; Fu, Qing; Shen, Aijin; Wang, Hui; Jin, Yu; Xin, Huaxia; Ke, Yanxiong; Guo, Zhimou; Liang, Xinmiao

    2015-04-01

    A diterpene glycoside compound, rebaudioside A (commonly abbreviated as RA), was immobilized onto porous silica surface through "thiol-ene" click chemistry strategy. The successful immobilization of the RA on the silica support was confirmed by FT-IR and elemental analysis. Chromatographic characteristics of the new stationary phase, named Click TE-RA, were evaluated by a set of diverse analytes such as carbohydrates, nucleosides, and organic acids in hydrophilic interaction liquid chromatography (HILIC) mode. The effects of water content, buffer pH and concentration were investigated and a typical HILIC retention feature of Click TE-RA was observed at high organic modifier content. The Click TE-RA stationary phase was further studied by a series of glycoside compounds. Tunable retention mechanisms from hydrophilic to hydrophobic interactions were observed. Separation of very polar compounds including oligosaccharides, nucleic acid bases and nucleosides using Click TE-RA in HILIC mode was successfully accomplished. In addition, separation of saponins both in HILIC and reversed-phase liquid chromatography (RPLC) modes was performed, demonstrating the presence of orthogonality between two different modes on Click TE-RA column. The multiple interactions induced by polar sugar group and hydrophobic aglycone group allowed this Click TE-RA to serve as a multi-mode stationary phase in two-dimensional liquid chromatography. PMID:25725956

  8. The impact of sewage sludge compost on tree peony growth and soil microbiological, and biochemical properties.

    PubMed

    Xue, Dong; Huang, Xiangdong

    2013-10-01

    In order to assess the suitability of sludge compost application for tree peony (Paeonia suffruticosa)-soil ecosystems, we determined soil microbial biomass C (Cmic), basal respiration (Rmic), enzyme activities, and tree peony growth parameters at 0-75% sludge compost amendment dosage. Soil Cmic, Rmic, Cmic as a percent of soil organic C, enzyme (invertase, urease, proteinase, phosphatase, polyphenoloxidase) activities, and plant height, flower diameter, and flower numbers per plant of tree peony significantly increased after sludge compost amendment; however, with the increasing sludge compost amendment dosage, a decreasing trend above 45% sludge compost amendment became apparent although soil organic C, total Kjeldahl N, and total P always increased with the sludge compost amendment. Soil metabolic quotient first showed a decreasing trend with the increasing sludge compost application in the range of 15-45%, and then an increasing trend from compost application of 45-75%, with the minimum found at compost application of 45%. As for the diseased plants, 50% of tree peony under the treatment without sludge compost amendment suffered from yellow leaf disease of tree peony, while no any disease was observed under the treatments with sludge compost application of 30-75%, which showed sludge compost application had significant suppressive effect on the yellow leaf disease of tree peony. This result convincingly demonstrated that ?45% sludge compost application dosage can take advantage of beneficial effect on tree peony growth and tree peony-soil ecosystems. PMID:23800593

  9. Rapid microsatellite development for tree peony and its implications

    PubMed Central

    2013-01-01

    Background Microsatellites are ubiquitous in genomes of various organisms. With the realization that they play roles in developmental and physiological processes, rather than exist as ‘junk’ DNA, microsatellites are receiving increasing attention. Next-generation sequencing allows acquisition of large-scale microsatellite information, and is especially useful for plants without reference genome sequences. Results In this study, enriched DNA libraries of tree peony, a well-known ornamental woody shrub, were used for high-throughput microsatellite development by 454 GS-FLX Titanium pyrosequencing. We obtained 675,221 reads with an average length of 356 bp. The total size of examined sequences was 240,672,018 bp, from which 237,134 SSRs were identified. Of these sequences, 164,043 contained SSRs, with 27% featuring more than one SSR. Interestingly, a high proportion of SSRs (43%) were present in compound formation. SSRs with repeat motifs of 1–4 bp (mono-, di-, tri-, and tetra-nucleotide repeats) accounted for 99.8% of SSRs. Di-nucleotide repeats were the most abundant. As in most plants, the predominant motif in tree peony was (A/T)n, with (G/C)n less common. The lengths of SSRs were classified into 11 groups. The shortest SSRs (10 bp) represented 1% of the total number, whereas SSRs 21–30 and 101–110 bp long accounted for 26% and 29%, respectively, of all SSRs. Many sequences (42,111) were mapped to CDS (coding domain sequence) regions using Arabidopsis as a reference. GO annotation analysis predicted that CDSs with SSRs performed various functions associated with cellular components, molecular functions, and biological processes. Of 100 validated primer pairs, 24 were selected for polymorphism analysis among 23 genotypes; cluster analysis of the resulting data grouped genotypes according to known relationships, confirming the usefulness of the developed SSR markers. Conclusions The results of our large-scale SSR marker development using tree peony are valuable for investigating plant genomic structural evolution and elucidating phenotypic variation in this species during its evolution and artificial selection. The newly identified SSRs should be useful for genetic linkage map construction, QTL mapping, gene location and cloning, and molecular marker-assisted breeding. In addition, the genome-wide marker resources generated in this study should aid genomic studies of tree peony and related species. PMID:24341681

  10. Transcriptome Comparison Reveals Key Candidate Genes Responsible for the Unusual Reblooming Trait in Tree Peonies

    PubMed Central

    Zhou, Hua; Cheng, Fang-Yun; Wang, Rong; Zhong, Yuan; He, Chaoying

    2013-01-01

    Tree peonies are important ornamental plants worldwide, but growing them can be frustrating due to their short and concentrated flowering period. Certain cultivars exhibit a reblooming trait that provides a valuable alternative for extending the flowering period. However, the genetic control of reblooming in tree peonies is not well understood. In this study, we compared the molecular properties and morphology of reblooming and non-reblooming tree peonies during the floral initiation and developmental processes. Using transcriptome sequencing technology, we generated 59,275 and 63,962 unigenes with a mean size of 698 bp and 699 bp from the two types of tree peonies, respectively, and identified eight differentially expressed genes that are involved in the floral pathways of Arabidopsis thaliana. These differentially regulated genes were verified through a detailed analysis of their expression pattern during the floral process by real time RT-PCR. From this combined analysis, we identified four genes, PsFT, PsVIN3, PsCO and PsGA20OX, which likely play important roles in the regulation of the reblooming process in tree peonies. These data constitute a valuable resource for the discovery of genes involved in flowering time and insights into the molecular mechanism of flowering to further accelerate the breeding of tree peonies and other perennial woody plants. PMID:24244590

  11. Identification of heat shock proteins via transcriptome profiling of tree peony leaf exposed to high temperature.

    PubMed

    Zhang, Y Z; Cheng, Y W; Ya, H Y; Han, J M; Zheng, L

    2015-01-01

    The tree peony leaf is an important vegetative organ that is sensitive to abiotic stress and particularly to high temperature. This sensitivity affects plant growth and restricts tree peony distribution. However, the transcriptomic information currently available on the peony leaf in public databases is limited. In this study, we sequenced the transcriptomes of peony leaves subjected to high temperature using the Illumina HiSeq TM 2000 platform. We performed de novo assembly of 93,714 unigenes (average length of 639.7 bp). By searching the public databases, 22,323 unigenes and 13,107 unigenes showed significant similarities with proteins in the NCBI non-redundant protein database and SWISS-PROT database (E-value < 1e-5), respectively. We assigned 17,340 unigenes to Gene Ontology categories, and we assigned 7618 unigenes to clusters of orthologous groups for eukaryotic complete genomes. By searching the Kyoto Encyclopedia of Genes and Genomes Pathway database, 8014 unigenes were assigned to 6 main categories, including 290 KEGG pathways. To advance research on improving thermotolerance, we identified 24 potential heat shock protein genes with complete open reading frames from the transcriptomic sequences. This is the first study to characterize the leaf transcriptome of tree peony leaf using high-throughput sequencing. The information obtained from the tree peony leaf is valuable for gene discovery, and the identified heat shock protein genes can be used to improve plant stress-tolerance. PMID:26345770

  12. Transcriptome sequencing of purple petal spot region in tree peony reveals differentially expressed anthocyanin structural genes

    PubMed Central

    Zhang, Yanzhao; Cheng, Yanwei; Ya, Huiyuan; Xu, Shuzhen; Han, Jianming

    2015-01-01

    The pigmented cells in defined region of a petal constitute the petal spots. Petal spots attract pollinators and are found in many angiosperm families. Several cultivars of tree peony contain a single red or purple spot at the base of petal that makes the flower more attractive for the ornamental market. So far, the understanding of the molecular mechanism of spot formation is inadequate. In this study, we sequenced the transcriptome of the purple spot and the white non-spot of tree peony flower. We assembled and annotated 67,892 unigenes. Comparative analyses of the two transcriptomes showed 1,573 differentially expressed genes, among which 933 were up-regulated, and 640 were down-regulated in the purple spot. Subsequently, we examined four anthocyanin structural genes, including PsCHS, PsF3?H, PsDFR, and PsANS, which expressed at a significantly higher level in the purple spot than in the white non-spot. We further validated the digital expression data using quantitative real-time PCR. Our result uncovered transcriptome variance between the spot and non-spot of tree peony flower, and revealed that the co-expression of four anthocyanin structural genes was responsible for spot pigment in tree peony. The data will further help to unravel the genetic mechanism of peony flower spot formation. PMID:26583029

  13. Multiple species of wild tree peonies gave rise to the king of flowers, Paeonia suffruticosa Andrews

    PubMed Central

    Zhou, Shi-Liang; Zou, Xin-Hui; Zhou, Zhi-Qin; Liu, Jing; Xu, Chao; Yu, Jing; Wang, Qiang; Zhang, Da-Ming; Wang, Xiao-Quan; Ge, Song; Sang, Tao; Pan, Kai-Yu; Hong, De-Yuan

    2014-01-01

    The origin of cultivated tree peonies, known as the king of flowers' in China for more than 1000 years, has attracted considerable interest, but remained unsolved. Here, we conducted phylogenetic analyses of explicitly sampled traditional cultivars of tree peonies and all wild species from the shrubby section Moutan of the genus Paeonia based on sequences of 14 fast-evolved chloroplast regions and 25 presumably single-copy nuclear markers identified from RNA-seq data. The phylogeny of the wild species inferred from the nuclear markers was fully resolved and largely congruent with morphology and classification. The incongruence between the nuclear and chloroplast trees suggested that there had been gene flow between the wild species. The comparison of nuclear and chloroplast phylogenies including cultivars showed that the cultivated tree peonies originated from homoploid hybridization among five wild species. Since the origin, thousands of cultivated varieties have spread worldwide, whereas four parental species are currently endangered or on the verge of extinction. The documentation of extensive homoploid hybridization involved in tree peony domestication provides new insights into the mechanisms underlying the origins of garden ornamentals and the way of preserving natural genetic resources through domestication. PMID:25377453

  14. Facile synthesis of three-dimensional hierarchical Co3O4 peony-like microspheres and their lithium storage performance

    NASA Astrophysics Data System (ADS)

    Che, Hongwei; Liu, Aifeng; Liang, Shunxing; Zhang, Xiaoliang; Mu, Jingbo; Bai, Yongmei; Hou, Junxian

    2015-07-01

    Three-dimensional hierarchical Co3O4 peony-like microspheres have been successfully synthesized via a facile ethylene glycol mediated solvothermal method combined with a subsequent calcination. The as-prepared peony-like microspheres are assembled by many intercrossed nanosheets with a thickness of 30 nm. The reaction conditions such as the amount of hexadecyl trimethyl ammonium bromide and sodium acetate as well as the solvothermal time are investigated to explore the effects on the morphology of the final Co3O4 products. According to these experiment results, a possible formation mechanism of the peony-like microspheres is proposed. Furthermore, when evaluated as anode materials for lithium storage, the Co3O4 peony-like microspheres exhibit high lithium storage capacity and good cycling performance, having a discharge capacity of 975 mA h g-1 at 100 mAg-1 after 50 cycles.

  15. Determination of eight artificial sweeteners and common Stevia rebaudiana glycosides in non-alcoholic and alcoholic beverages by reversed-phase liquid chromatography coupled with tandem mass spectrometry.

    PubMed

    Kubica, Paweł; Namieśnik, Jacek; Wasik, Andrzej

    2015-02-01

    The method for the determination of acesulfame-K, saccharine, cyclamate, aspartame, sucralose, alitame, neohesperidin dihydrochalcone, neotame and five common steviol glycosides (rebaudioside A, rebaudioside C, steviol, steviolbioside and stevioside) in soft and alcoholic beverages was developed using high-performance liquid chromatography and tandem mass spectrometry with electrospray ionisation (HPLC-ESI-MS/MS). To the best of our knowledge, this is the first work that presents an HPLC-ESI-MS/MS method which allows for the simultaneous determination of all EU-authorised high-potency sweeteners (thaumatin being the only exception) in one analytical run. The minimalistic sample preparation procedure consisted of only two operations; dilution and centrifugation. Linearity, limits of detection and quantitation, repeatability, and trueness of the method were evaluated. The obtained recoveries at three tested concentration levels varied from 97.0 to 105.7%, with relative standard deviations lower than 4.1%. The proposed method was successfully applied for the determination of sweeteners in 24 samples of different soft and alcoholic drinks. PMID:25471292

  16. [Effects of different peony cultivars on community structure of arbuscular mycorrhizal fungi in rhizosphere soil].

    PubMed

    Guo, Shao-Xia; Liu, Run-Jin

    2010-08-01

    This paper studied the community structure of arbuscular mycorrhizal (AM) fungi in the rhizosphere soil of different peony (Paeonia suffruticosa) cultivars grown in Zhaolou Peony Garden of Heze in Shandong Province. A number of parameters describing this community structure, e. g., spore density, species- and genera composition, species richness, distribution frequency, species diversity indices, and Sorenson's similarity coefficient, were examined. The species- and genera composition, species richness, and distribution frequency of AM fungi in rhizosphere soil varied with planted peony cultivars. A total of 10 AM fungal species were isolated from the rhizosphere soil of cultivars 'Fengdan' and 'Zhaofen', 9 species from the rhizosphere soil of 'Wulong pengsheng' and 'Luoyang red', and 8 species from the rhizosphere soil of 'Hu red'. The spore density was the highest (59 per 50 g soil) in the rhizosphere soil of 'Fengdan', but the lowest (47 per 50 g soil) in the rhizosphere soil of 'Hu red'; the species diversity index was the highest (1.89) in the rhizosphere soil of 'Zhaofen', but the lowest (1.71) in the rhizosphere soil of 'Hu red'; and the mycorrhizal colonization rate was the highest (63.6%) in rhizosphere soil of 'Fengdan' and 'Hu red', but the lowest (52.7%) in the rhizosphere soil of 'Wulong pengsheng'. The Sorenson's similarity coefficient of AM fungal species composition in the rhizosphere soil among the test cultivars ranged from 0.71 to 0.95, being the highest between 'Wulong pengsheng' and 'Fengdan', and the lowest between 'Luoyang red' and 'Hu red'. It was concluded that the gene type of peony could change the community structure of AM fungi in rhizosphere soil. PMID:21043106

  17. Reversals.

    ERIC Educational Resources Information Center

    National Center on Educational Media and Materials for the Handicapped, Columbus, OH.

    Selected from the National Instructional Materials Information System (NIMIS)--a computer based on-line interactive retrieval system on special education materials--the bibliography covers nine materials for remediating reversals in handicapped students at the early childhood and elementary levels. Entries are presented in order of NIMIS accession

  18. Total glucosides of peony attenuates experimental autoimmune encephalomyelitis in C57BL/6 mice.

    PubMed

    Huang, Qiling; Ma, Xiaomeng; Zhu, Dong Liang; Chen, Li; Jiang, Ying; Zhou, Linli; Cen, Lei; Pi, Rongbiao; Chen, Xiaohong

    2015-07-15

    Total glucosides of peony (TGP), an active compound extracted from the roots of Paeonia lactiflora Pall, has wide pharmacological effects on nervous system. Here we examined the effects of TGP on experimental autoimmune encephalomyelitis (EAE), an established model of multiple sclerosis (MS). The results showed that TGP can reduce the severity and progression of EAE in C57 BL/6 mice. In addition, TGP also down-regulated the Th1/Th17 inflammatory response and prevented the reduced expression of brain-derived neurotrophic factor and 2',3'-cyclic nucleotide 3'-phosphodiesterase of EAE. These findings suggest that TGP could be a potential therapeutic agent for MS. PMID:26025060

  19. Anticancer activity of sea cucumber triterpene glycosides.

    PubMed

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

    2015-03-01

    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-?B, 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

  20. Anticancer Activity of Sea Cucumber Triterpene Glycosides

    PubMed Central

    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

  1. Evaluation of absorbed dose in irradiated sugar-containing plant material (peony roots) by an ESR method

    NASA Astrophysics Data System (ADS)

    Yamaoki, Rumi; Kimura, Shojiro; Ohta, Masatoshi

    2015-12-01

    The relationship between electron spin resonance (ESR) signal intensity of irradiated plant materials and sugar content was investigated by spectral analysis using peony roots. A weak background signal near g=2.005 was observed in the roots. After a 10 kGy irradiation, the ESR line broadened and the intensity increased, and the spectral characteristics were similar to a typical spectrum of irradiated food containing crystalline sugars. The free radical concentration was nearly stable 30 days after irradiation. The spectrum of peony root 30 days after irradiation was simulated using the summation of the intensities of six assumed components: radical signals derived from (a) sucrose, (b) glucose, (c) fructose, (d) cellulose, (e) the background signal near g=2.005 and (f) unidentified component. The simulated spectra using the six components were in agreement with the observed sample spectra. The intensity of sucrose radical signal in irradiated samples increased proportionally up to 20 kGy. In addition, the intensity of sucrose radical signals was strongly correlated with the sucrose contents of the samples. The results showed that the radiation sensitivity of sucrose in peony roots was influenced little by other plant constituents. There was also a good correlation between the total area of the spectra and the sucrose content, because the sucrose content was higher than that of other sugars in the samples. In peony roots, estimation of the absorbed dose from the ESR signal intensity may be possible by a calibration method based on the sucrose content.

  2. 75 FR 65648 - Notice of Proposed Withdrawal Extension and Opportunity for Public Meeting for the Peony, Pole...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-10-26

    ... Secretary of the Interior for Land and Minerals Management extend PLO No. 6952 (57 FR 53587 (1992)), which... and functionality of the seed orchards, along with the investment of Federal funds at the Peony, Pole... proposed withdrawal extension is to continue the protection of the integrity and functionality of the...

  3. Transcriptome analysis of tree peony during chilling requirement fulfillment: assembling, annotation and markers discovering.

    PubMed

    Gai, Shupeng; Zhang, Yuxi; Mu, Ping; Liu, Chunying; Liu, Shao; Dong, Lei; Zheng, Guosheng

    2012-04-15

    Tree peony (Paeonia suffruticosa Andrews) is a well-known horticultural and medicinal plant. The flower buds must go through a period of endo-dormancy before bud sprouting in winter, but very little information concerned with dormancy release is available. We obtained 625,342 sequencing reads with massive parallel pyrosequencing on the Roche 454 GS FLX platform (mean length: 358.1bp). De novo assemblies yielded 23,652 contigs and singletons. 15,284 contigs longer than 300bp were further annotated, among them 12,345 ESTs showed significant similarity with sequences present in public databases (with an E-value <1e-10). 484 putative transcription factors were obtained. In addition, 2253 potential Simple Sequence Repeats (SSR) loci were identified in the 454-ESTs. Total 149 pairs of primers were designed, and 121 pairs were amplified successfully in initial screening. In addition, 73 pairs of primers displayed polymorphism. This sequence collection provides a significant resource for gene discovery during endo-dormancy of tree peony. PMID:22197659

  4. Anti-diabetic activity of peony seed oil, a new resource food in STZ-induced diabetic mice.

    PubMed

    Su, Jianhui; Wang, Hongxin; Ma, Caoyang; Lou, Zaixiang; Liu, Chengxiang; Tanver Rahman, MdRamim; Gao, Chuanzhong; Nie, Rongjing

    2015-09-01

    This study was conducted to investigate the components of a new resource food in China, peony seed oil (PSO) by GC-MS (gas chromatography-mass spectrometry), its inhibitory effects on carbohydrate hydrolyzing enzymes in vitro and its anti-diabetic effects on mice induced by streptozotocin (STZ). The results showed that peony seed oil showed weak anti-α-amylase activity; however, strong anti-α-glucosidase activity was noted. The GC-MS analysis of the oil showed 9 constituents of which α-linolenic acid was found to be the major component (38.66%), followed by linoleic acid (26.34%) and oleic acid (23.65%). The anti-diabetic potential of peony seed oil was tested in STZ induced diabetic mice. Administration of peony seed oil and glibenclamide reduced the blood glucose level and the area under curve (AUC) in STZ induced diabetic mice. There were significant increases in body weight, liver glycogen content, serum insulin level, high-density lipoprotein cholesterol (HDL-C) and decreases in glycosylated hemoglobin (HbA1C), total serum cholesterol (TC), and triglyceride (TG) in test groups as compared to the untreated diabetic groups. In vivo antioxidant studies on STZ induced diabetic mice revealed the reduction of malondialdehyde (MDA) and increase of glutathione peroxides (GSH-px), superoxide dismutase (SOD), and glutathione (GSH). The results provided a sound rationale for future clinical trials of oral administration of peony seed oil to alleviate postprandial hyperglycemia in streptozotocin-induced diabetic mice. PMID:26245697

  5. Variants of glycoside hydrolases

    SciTech Connect

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

    2013-02-26

    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.

  6. Variants of glycoside hydrolases

    DOEpatents

    Teter, Sarah (Davis, CA); Ward, Connie (Hamilton, MT); Cherry, Joel (Davis, CA); Jones, Aubrey (Davis, CA); Harris, Paul (Carnation, WA); Yi, Jung (Sacramento, CA)

    2011-04-26

    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.

  7. Chemical taxonomy of tree peony species from China based on root cortex metabolic fingerprinting.

    PubMed

    He, Chunnian; Peng, Bing; Dan, Yang; Peng, Yong; Xiao, Peigen

    2014-11-01

    The section Moutan of the genus Paeonia consists of eight species that are confined to a small area in China. A wide range of metabolites, including monoterpenoid glucosides, flavonoids, tannins, stilbenes, triterpenoids, steroids, paeonols, and phenols, have been found in the species belonging to section Moutan. However, although previous studies have analyzed the metabolites found in these species, the metabolic similarities that can be used for the chemotaxonomic distinction of section Moutan species are not yet clear. In this study, HPLC-DAD-based metabolic fingerprinting was applied to the classification of eight species: Paeoniasuffruticosa, Paeoniaqiui, Paeoniaostii, Paeoniarockii, Paeoniajishanensis, Paeoniadecomposita, Paeoniadelavayi, and Paeonialudlowii. In total, of the 47 peaks that exhibited an occurrence frequency of 75% in all 23 tree peony samples, 43 of these metabolites were identified according to their retention times and UV absorption spectra, together with combined HPLC-QTOF-MS. These data were compared with reference standard compounds. The 43 isolated compounds included 17 monoterpenoid glucosides, 11 galloyl glucoses, 5 flavonoids, 6 paeonols and 4 phenols. Principal component analysis (PCA), and hierarchical cluster analysis (HCA), showed a clear separation between the species based on metabolomics similarities and four groups were identified. The results exhibited good agreement with the classical classification based on the morphological characteristics and geographical distributions of the subsections Vaginatae F.C. Stern and Delavayanae F.C. Stern with the exception of P. decomposita, which was found to be a transition species between these two subsections. According to their metabolic fingerprinting characteristics, P. ostii and P. suffruticosa can be considered one species, and this result is consistent with the viewpoint of medicinal plant scientists but different from that of classical morphological processing. Significantly large variations were obtained in the metabolic profiles of P. delavayi, whereas no significant difference was found between P. delavayi and P. ludlowii. This indicates that these two species have a close genetic relationship. In conclusion, the combination of HPLC-DAD and multivariate analyses has great potential for guiding future chemotaxonomic studies to examine the potential pharmaceutical value of the effective constituents of tree peony species and appears to be able to clarify the confusion and skepticism associated with the reported morphology- and molecular phylogenetics-based taxonomy of tree peonies. PMID:25220499

  8. Enzymatic synthesis using glycoside phosphorylases

    PubMed Central

    O’Neill, Ellis C.; Field, Robert A.

    2015-01-01

    Carbohydrate phosphorylases are readily accessible but under-explored catalysts for glycoside synthesis. Their use of accessible and relatively stable sugar phosphates as donor substrates underlies their potential. A wide range of these enzymes has been reported of late, displaying a range of preferences for sugar donors, acceptors and glycosidic linkages. This has allowed this class of enzymes to be used in the synthesis of diverse carbohydrate structures, including at the industrial scale. As more phosphorylase enzymes are discovered, access to further difficult to synthesise glycosides will be enabled. Herein we review reported phosphorylase enzymes and the glycoside products that they have been used to synthesise. PMID:25060838

  9. Monoterpene derivatives with anti-allergic activity from red peony root, the root of Paeonia lactiflora.

    PubMed

    Shi, Yan-Hong; Zhu, Shu; Ge, Yue-Wei; He, Yu-Min; Kazuma, Kohei; Wang, Zhengtao; Yoshimatsu, Kayo; Komatsu, Katsuko

    2016-01-01

    The methanolic extract and its subfractions from red peony root, the dried roots of Paeonia lactiflora Pallas showed potent antiallergic effects, as inhibition of immunoglobulin E (IgE)-mediated degranulation in rat basophil leukemia (RBL)-2H3 cells. Bioassay-guided fractionation led to the isolation of 16 monoterpene derivatives, including 3 new compounds, paeoniflorol (1), 4'-hydroxypaeoniflorigenone (2) and 4-epi-albiflorin (3), together with 13 known ones (4-16). The chemical structures of the new compounds were elucidated on the basis of spectroscopic and chemical evidences. Among the isolated monoterpene derivatives, nine compounds showed potent anti-allergic effects and compound 1 was the most effective. A primary structure-activity relationship of monoterpene derivatives was discussed. PMID:26598138

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

    NASA Astrophysics Data System (ADS)

    K?en, Vladimr

    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.

  11. Microwave-Assisted Simultaneous Extraction of Luteolin and Apigenin from Tree Peony Pod and Evaluation of Its Antioxidant Activity

    PubMed Central

    Wang, Hongzheng; Yang, Lei; Zu, Yuangang; Zhao, Xiuhua

    2014-01-01

    An efficient microwave-assisted extraction (MAE) technique was employed in simultaneous extraction of luteolin and apigenin from tree peony pod. The MAE procedure was optimized using response surface methodology (RSM) and compared with other conventional extraction techniques of macerate extraction (ME) and heat reflux extraction (HRE). The optimal conditions of MAE were as follows: employing 70% ethanol volume fraction as solvent, soaking time of 4 h, liquid-solid ratio of 10 (mL/g), microwave irradiation power of 265 W, microwave irradiation time of 9.6 min, and 3 extraction cycles. Under the optimal conditions, 151 μg/g luteolin and 104 μg/g apigenin were extracted from the tree peony pod. Compared with ME and HRE, MAE gave the highest extraction efficiency. The antioxidant activities of the extracts obtained by MAE, ME, and HRE were evaluated using a 2,2-di(4-tert-octylphenyl)-1-picrylhydrazyl (DPPH) free radical-scavenging assay, a ferric reducing antioxidant power assay (FRAP), and a reducing power assay. Meanwhile, the structural changes of the unprocessed and processed tree peony pod samples were analyzed by scanning electron microscopy. PMID:25405227

  12. Synthesis and Photochromic Properties of Configurationally Varied Azobenzene Glycosides

    PubMed Central

    Chandrasekaran, Vijayanand; Johannes, Eugen; Kobarg, Hauke; Snnichsen, Frank D; Lindhorst, Thisbe K

    2014-01-01

    Spatial orientation of carbohydrates is a meaningful parameter in carbohydrate recognition processes. To vary orientation of sugars with temporal and spatial resolution, photosensitive glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow switching of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photochromic properties were tested and effects of azobenzene substitution as well as the effect of anomeric configuration and the orientation of the sugars 2-hydroxy group were evaluated. PMID:25050228

  13. Isoflavone glycosides from Derris scandens.

    PubMed

    Rukachaisirikul, Vatcharin; Sukpondma, Yaowapa; Jansakul, Chaweewan; Taylor, Walter C

    2002-08-01

    Five isoflavone glycosides, named derriscandenosides A-E (1-5), were isolated from the stems of Derris scandens, together with ten known compounds comprising one isoflavone, two benzoic acid derivatives, three glucosyl isoflavones and four rhamnosyl-(1-->6)-glucosyl isoflavones. The structures of the glycosides were assigned on the basis of spectroscopic data, especially of the acetate derivatives. Three known rhamnosyl-(1-->6)-glucosyl isoflavones isolated from a crude fraction were retested for hypotensive activity with varying results. PMID:12150808

  14. Analysis of Codon Usage Patterns in Herbaceous Peony (Paeonia lactiflora Pall.) Based on Transcriptome Data

    PubMed Central

    Wu, Yanqing; Zhao, Daqiu; Tao, Jun

    2015-01-01

    Codon usage bias, which exists in many genomes, is mainly determined by mutation and selection. To elucidate the genetic features and evolutionary history of herbaceous peony (Paeonia lactiflora), a well-known symbol of prosperity in China, we examined synonymous codon usage in 24,216 reconstructed genes from the P. lactiflora transcriptome. The mean GC content was 44.4%, indicating that the nucleotide content of P. lactiflora genes is slightly AT rich and GC poor. The P. lactiflora genome has a wide range of GC3 (GC content at the third synonymous codon position) distribution, with a significant correlation between GC12 and GC3. ENC (effective number of codons) analysis suggested that mutational bias played a major role in shaping codon usage. Parity Rule 2 (PR2) analysis revealed that GC and AU were not used proportionally. We identified 22 “optimal codons”, most ending with an A or U. Our results suggested that nucleotide composition mutation bias and translational selection were the main driving factors of codon usage bias in P. lactiflora. These results lay the foundation for exploring the evolutionary mechanisms and heterologous expression of functionally-important proteins in P. lactiflora. PMID:26506393

  15. Quantitative Proteomics Analysis of Herbaceous Peony in Response to Paclobutrazol Inhibition of Lateral Branching

    PubMed Central

    Zhao, Daqiu; Gong, Saijie; Hao, Zhaojun; Meng, Jiasong; Tao, Jun

    2015-01-01

    Herbaceous peony (Paeonia lactiflora Pall.) is an emerging high-grade cut flower worldwide, which is usually used in wedding bouquets and known as the “wedding flower”. However, abundant lateral branches appear frequently in some excellent cultivars, and a lack of a method to remove Paeonia lactiflora lateral branches other than inefficient artificial methods is an obstacle for improving the quality of its cut flowers. In this study, paclobutrazol (PBZ) application was found to inhibit the growth of lateral branches in Paeonia lactiflora for the first time, including 96.82% decreased lateral bud number per branch, 77.79% and 42.31% decreased length and diameter of lateral branches, respectively, declined cell wall materials and changed microstructures. Subsequently, isobaric tag for relative and absolute quantitation (iTRAQ) technology was used for quantitative proteomics analysis of lateral branches under PBZ application and control. The results indicated that 178 differentially expressed proteins (DEPs) successfully obtained, 98 DEPs were up-regulated and 80 DEPs were down-regulated. Thereafter, 34 candidate DEPs associated with the inhibited growth of lateral branches were screened according to their function and classification. These PBZ-stress responsive candidate DEPs were involved in eight biological processes, which played a very important role in the growth and development of lateral branches together with the response to PBZ stress. These results provide a better understanding of the molecular theoretical basis for removing Paeonia lactiflora lateral branches using PBZ application. PMID:26473855

  16. Quantitative Proteomics Analysis of Herbaceous Peony in Response to Paclobutrazol Inhibition of Lateral Branching.

    PubMed

    Zhao, Daqiu; Gong, Saijie; Hao, Zhaojun; Meng, Jiasong; Tao, Jun

    2015-01-01

    Herbaceous peony (Paeonia lactiflora Pall.) is an emerging high-grade cut flower worldwide, which is usually used in wedding bouquets and known as the "wedding flower". However, abundant lateral branches appear frequently in some excellent cultivars, and a lack of a method to remove Paeonia lactiflora lateral branches other than inefficient artificial methods is an obstacle for improving the quality of its cut flowers. In this study, paclobutrazol (PBZ) application was found to inhibit the growth of lateral branches in Paeonia lactiflora for the first time, including 96.82% decreased lateral bud number per branch, 77.79% and 42.31% decreased length and diameter of lateral branches, respectively, declined cell wall materials and changed microstructures. Subsequently, isobaric tag for relative and absolute quantitation (iTRAQ) technology was used for quantitative proteomics analysis of lateral branches under PBZ application and control. The results indicated that 178 differentially expressed proteins (DEPs) successfully obtained, 98 DEPs were up-regulated and 80 DEPs were down-regulated. Thereafter, 34 candidate DEPs associated with the inhibited growth of lateral branches were screened according to their function and classification. These PBZ-stress responsive candidate DEPs were involved in eight biological processes, which played a very important role in the growth and development of lateral branches together with the response to PBZ stress. These results provide a better understanding of the molecular theoretical basis for removing Paeonia lactiflora lateral branches using PBZ application. PMID:26473855

  17. Cardiac glycoside receptor in potassium depletion.

    PubMed

    Erdmann, E; Bolte, H D; Schoner, W

    1975-01-01

    Ouabain binding capacity of cell membranes is directly related to (Na+ + K+)-ATPase activity. The extent of ouabain inhibition of (Na+ + K+)-ATPase is a measure of ouabain receptor sites occupied. Dissociation constants of the ouabain-receptor complexes are identical in all organs in a single species but vary among different species. K+ decreases the association rate constant of the ouabain receptor interaction without altering the dissociation rate constants. Titration of digoxin-inhibited (Na+ + K+)-ATPase from guinea pig heart with digoxin antibodies shows a reversal of the inhibition at lower antibody concentrations in the presence of K+ than in the absence of K+. It is concluded that digitalis intolerance in acute hypokalemia reflects the increased affinity of the cardiac glycoside receptor under these conditions. PMID:127357

  18. Anatomical and biochemical analysis reveal the role of anthocyanins in flower coloration of herbaceous peony.

    PubMed

    Zhao, Da-Qiu; Wei, Meng-Ran; Liu, Ding; Tao, Jun

    2016-05-01

    Herbaceous peony (Paeonia lactiflora Pall.) is particularly appreciated because of its elegant and gorgeous flower color, but little is known about the underlying mechanisms of flower coloration. In this study, three P. lactiflora cultivars 'Xuefeng', 'Fenyulou' and 'Dahonglou' with white, pink and red flower were selected as the materials. Their anatomical structures, cell sap pH and metal elements were investigated, and the colored pigment mainly distributed in palisade mesophyll was only found in 'Fenyulou' and 'Dahonglou', and their shape of epidermal cells, cell sap pH and metal elements were not the key factors deciding phenotype color. Moreover, the qualitative and quantitative analysis of flavonoids were performed, their total anthocyanin, anthoxanthin and flavonoid contents were decreased during flower development, and only anthocyanin content in 'Dahonglou' was always higher than that in 'Xuefeng' and 'Fenyulou'. Subsequently, three anthocyanin compositions were found, and peonidin 3,5-di-O-glucoside (Pn3G5G) was identified as the main anthocyanin composition. In addition, the full-length of flavonol synthase gene (FLS) was isolated with the GenBank accession number KM259902, and the expression patterns of eight flavonoid biosynthetic genes showed that only PlDFR and PlANS basically had the highest levels in 'Dahonglou' and the lowest levels in 'Xuefeng', and they basically displayed a descended trend during flower development especially PlDFR, suggesting that these two genes might play a key role in the anthocyanin biosynthesis which resulted in the shift from white to pink and red in flowers. These results would contribute to understand the underlying molecular mechanisms of flower coloration in P. lactiflora. PMID:26922162

  19. Changes in soil microbial functional diversity and biochemical characteristics of tree peony with amendment of sewage sludge compost.

    PubMed

    Huang, Xiangdong; Xue, Dong; Xue, Lian

    2015-08-01

    A greenhouse experiment was conducted to investigate the impact of sewage sludge compost application on functional diversity of soil microbial communities, based on carbon source utilization, and biochemical characteristics of tree peony (Paeonia suffruticosa). Functional diversity was estimated with incubations in Biolog EcoPlates and well color development was used as the functional trait for carbon source utilization. The average well color development and Shannon index based on the carbon source utilization pattern in Biolog EcoPlates significantly increased with the increasing sludge compost application in the range of 0-45%, with a decreasing trend above 45%. Principal component analysis of carbon source utilization pattern showed that sludge compost application stimulated the utilization rate of D-cellobiose and ?-D-lactose, while the utilization rate of ?-methyl-D-glucoside, L-asparagine, L-serine, ?-cyclodextrin, ?-hydroxybutyric acid, and itaconic acid gradually increased up to a sludge compost amendment dosage of 45% and then decreased above 45%. The chlorophyll content, antioxidase (superoxide dismutase, catalase, and peroxidase) activities, plant height, flower diameter, and flower numbers per plant of tree peony increased significantly with sludge compost dosage, reaching a peak value at 45 %, and then decreased with the exception that activity of superoxide dismutase and catalase did not vary significantly. PMID:25847444

  20. Flavonol Glycosides from Gaura Biennis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phytochemical investigation of the native American plant Gaura biennis led to the isolation of three new flavonol glycosides (1-3), along with eight known ones. Their structures were established primarily by spectroscopic data as quercetin 3-O-(2"-O-a-L-rhamnopyranosyl-6"-O-E-p-coumaroyl)-ß-D- gluco...

  1. Cyanogenetic glycosides and simple glycosides from the linseed meal.

    PubMed

    Yang, Qing-Yun; Song, Li; Zhang, Ji-Fa; Shen, Zhu-Fang; Liu, Quan; Liu, Shuai-Nan; Zheng, Wen-Sheng; Yao, Chun-Suo

    2015-10-01

    Three new cyanogenetic triglycosides linustatins A-C (1-3), and two new simple glycosides linustatins D and E (4 and 5) were isolated from the 70% ethanol extract of flaxseed meal (Linum usitatissimum L.). Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates showed moderate activities against aldose reductase and weak activities against α-glucosidase, DPP-IV, and FBPase at the same concentrations as the positive control drugs. PMID:26307006

  2. Digital Gene Expression Analysis to Screen Disease Resistance-Relevant Genes from Leaves of Herbaceous Peony (Paeonia lactiflora Pall.) Infected by Botrytis cinerea

    PubMed Central

    Gong, Saijie; Hao, Zhaojun; Meng, Jiasong; Liu, Ding; Wei, Mengran; Tao, Jun

    2015-01-01

    Herbaceous peony (Paeonia lactiflora Pall.) is a well-known traditional flower in China and is widely used for landscaping and garden greening due to its high ornamental value. However, disease spots usually appear after the flowering of the plant and may result in the withering of the plant in severe cases. This study examined the disease incidence in an herbaceous peony field in the Yangzhou region, Jiangsu Province. Based on morphological characteristics and molecular data, the disease in this area was identified as a gray mold caused by Botrytis cinerea. Based on previously obtained transcriptome data, eight libraries generated from two herbaceous peony cultivars ‘Zifengyu’ and ‘Dafugui’ with different susceptibilities to the disease were then analyzed using digital gene expression profiling (DGE). Thousands of differentially expressed genes (DEGs) were screened by comparing the eight samples, and these genes were annotated using the Gene ontology (GO) and Kyoto encyclopedia of genes and genomes (KEGG) database. The pathways related to plant-pathogen interaction, secondary metabolism synthesis and antioxidant system were concentrated, and 51, 76, and 13 disease resistance-relevant candidate genes were identified, respectively. The expression patterns of these candidate genes differed between the two cultivars: their expression of the disease-resistant cultivar ‘Zifengyu’ sharply increased during the early stages of infection, while it was relatively subdued in the disease-sensitive cultivar ‘Dafugui’. A selection of ten candidate genes was evaluated by quantitative real-time PCR (qRT-PCR) to validate the DGE data. These results revealed the transcriptional changes that took place during the interaction of herbaceous peony with B. cinerea, providing insight into the molecular mechanisms of host resistance to gray mold. PMID:26208357

  3. Digital Gene Expression Analysis to Screen Disease Resistance-Relevant Genes from Leaves of Herbaceous Peony (Paeonia lactiflora Pall.) Infected by Botrytis cinerea.

    PubMed

    Gong, Saijie; Hao, Zhaojun; Meng, Jiasong; Liu, Ding; Wei, Mengran; Tao, Jun

    2015-01-01

    Herbaceous peony (Paeonia lactiflora Pall.) is a well-known traditional flower in China and is widely used for landscaping and garden greening due to its high ornamental value. However, disease spots usually appear after the flowering of the plant and may result in the withering of the plant in severe cases. This study examined the disease incidence in an herbaceous peony field in the Yangzhou region, Jiangsu Province. Based on morphological characteristics and molecular data, the disease in this area was identified as a gray mold caused by Botrytis cinerea. Based on previously obtained transcriptome data, eight libraries generated from two herbaceous peony cultivars 'Zifengyu' and 'Dafugui' with different susceptibilities to the disease were then analyzed using digital gene expression profiling (DGE). Thousands of differentially expressed genes (DEGs) were screened by comparing the eight samples, and these genes were annotated using the Gene ontology (GO) and Kyoto encyclopedia of genes and genomes (KEGG) database. The pathways related to plant-pathogen interaction, secondary metabolism synthesis and antioxidant system were concentrated, and 51, 76, and 13 disease resistance-relevant candidate genes were identified, respectively. The expression patterns of these candidate genes differed between the two cultivars: their expression of the disease-resistant cultivar 'Zifengyu' sharply increased during the early stages of infection, while it was relatively subdued in the disease-sensitive cultivar 'Dafugui'. A selection of ten candidate genes was evaluated by quantitative real-time PCR (qRT-PCR) to validate the DGE data. These results revealed the transcriptional changes that took place during the interaction of herbaceous peony with B. cinerea, providing insight into the molecular mechanisms of host resistance to gray mold. PMID:26208357

  4. Phenolic glycosides from Potalia amara.

    PubMed

    Li, Xing-Cong; ElSohly, Hala N; Walker, Larry A; Clark, Alice M

    2005-10-01

    Investigation of the stem bark of the unique Amazonian herbal plant Potalia amara yielded two new phenolic glycosides, potalioside A (1) and B (2), along with di-O-methylcrenatin (3), 2,6-dimethoxy-4-hydroxyphenol 1-glucoside and sweroside. The structures of potalioside A and B were established by interpretation of spectral data as 4-hydroxymethyl-2,6-dimethoxyphenyl 1-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside and 4-hydroxymethyl-2,6-dimethoxyphenyl 1-O-beta- D-xylopyranosyl(1-->6)- beta-D-glucopyranoside, respectively. PMID:16254836

  5. Two New Triterpene Glycosides from Centella asiatica

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  6. Five new steroidal glycosides from the stems of Solanum sodomaeum.

    PubMed

    Ono, Masateru; Uenosono, Yuuki; Umaoka, Hideharu; Shiono, Yuki; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

    2009-07-01

    Besides 12 known glycosides, five new steroidal glycosides have been isolated from the stems of Solanum sodomaeum L. (Solanaceae). The chemical structures of these five glycosides were determined on the basis of spectroscopic data as well as chemical evidence, and the structure of one known steroidal glycoside was corrected. PMID:19571429

  7. Analysis of heartsease (Viola tricolor L.) flavonoid glycosides by micro-liquid chromatography coupled to multistage mass spectrometry.

    PubMed

    Vukics, Viktoria; Ringer, Thomas; Kery, Agnes; Bonn, Guenther K; Guttman, Andras

    2008-10-01

    Micro-liquid chromatography (microLC) in conjunction with multistage mass spectrometry (MSn) was introduced to study several major heartsease flavonoid glycosides. High-resolution microLC separation was achieved by using a monolithic poly(p-methylstyrene-co-1,2-bis(p-vinylphenyl)ethane) column under reversed-phase conditions. The MS/MS and MS3 analysis of the flavonoid components of interest provided data about their glycosylation type and position, nature of their aglycones, and the structure/linkage information of their glycan moieties. With our microLC-MSn approach, four flavonol O-glycosides, nine flavone-C-glycosides, and three flavone C,O-glycosides were characterized in heartsease methanol extract. All of these glycoconjugates were found to be the derivatives of six aglycones: apigenin, chrysoeriol, isorhamnetin, kaempferol, luteolin, and quercetin. PMID:18514209

  8. Antibiofilm phenylethanoid glycosides from Penstemon centranthifolius.

    PubMed

    Ye, Miao; Zhao, Yun; Norman, Vanessa L; Starks, Courtney M; Rice, Stephanie M; Goering, Matt G; O'Neil-Johnson, Mark; Eldridge, Gary R; Hu, Jin-Feng

    2010-05-01

    Bioassay-guided fractionation of the antibacterial ethyl acetate-ethanol (50 : 50) extract obtained from the aerial parts of Penstemon centranthifolius led to the isolation of six phenylethanoid glycosides (1-6) and eleven iridoid glycosides (7-17). Their structures were determined on the basis of spectroscopic analysis and comparison with the literature. Among them, two phenylethanoid glycosides, 4'''-O-acetylverbascoside (1) and verbascoside (2), were found to show significant inhibition of the formation of bacterial biofilms by Escherichia coli UTI89. Compound 1 showed 77% biofilm inhibition at 2.5 microg/mL, and compound 2 showed 60% inhibition at 5 microg/mL. PMID:19827017

  9. Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides.

    PubMed

    Christensen, J; Jaroszewski, J W

    2001-07-12

    [structure: see text] Leaves of the edible passion fruit plant, Passiflora edulis, contain benzylic beta-D-allopyranosides 1 and 2, representatives of a rare class of natural glycosides with D-allose as the only sugar constituent. The glycoside 1 is the first known cyanogenic glycoside containing a sugar different from D-glucose attached directly to the cyanohydrin center. Asymmetric perturbation of the (1)L(b) transition of the benzene chromophore was shown to be useful for determination of absolute configuration of the cyanohydrin center of aromatic cyanogenic glycosides. PMID:11440577

  10. Stereoselective Synthesis of ?-manno-Glycosides

    NASA Astrophysics Data System (ADS)

    Ishiwata, Akihiro; Ito, Yukishige

    Among the various types of O-glycosides with biological relevance, the ?-glycoside of D-mannose (?-manno-glycoside) has been considered as one of the most challenging targets from a synthetic point of view. The majority of synthetic approaches to ?-manno-glycoside can be put into two categories (the direct glycosylation and the glycosylation-inversion approaches). Additionally, a variety of intriguing approaches have been investigated with substantial success (alkylative glycosylation of 1,2-stannylene acetal, reductive manipulation of orthoester, intramolecular aglycon delivery, and enzymatic glycosylation). In this chapter, progress in the conceptually demanding ?-mannosylation technology will be discussed, including current state of the art, with particular focus upon applications related to the synthesis of glycoprotein-related oligosaccharides.

  11. Three new glycosides from Hylocereus undatus.

    PubMed

    Wu, Xin; Wang, Ying; Huang, Xiao-Jun; Fan, Chun-Lin; Wang, Guo-Cai; Zhang, Xiao-Qi; Zhang, Qin-Wen; Ye, Wen-Cai

    2011-08-01

    Three new glycosides, undatusides A-C (1-3), and 11 known compounds (4-14) were isolated from the flowers of Hylocereus undatus. Their structures were elucidated on the basis of spectroscopic data and chemical method. PMID:21751841

  12. The First High-Density Genetic Map Construction in Tree Peony (Paeonia Sect. Moutan) using Genotyping by Specific-Locus Amplified Fragment Sequencing

    PubMed Central

    Cai, Changfu; Cheng, Fang-Yun; Wu, Jing; Zhong, Yuan; Liu, Gaixiu

    2015-01-01

    Genetic linkage maps, permitting the elucidation of genome structure, are one of most powerful genomic tools to accelerate marker-assisted breeding. However, due to a lack of sufficient user-friendly molecular markers, no genetic linkage map has been developed for tree peonies (Paeonia Sect. Moutan), a group of important horticultural plants worldwide. Specific-locus amplified fragment sequencing (SLAF-seq) is a recent molecular marker development technology that enable the large-scale discovery and genotyping of sequence-based marker in genome-wide. In this study, we performed SLAF sequencing of an F1 population, derived from the cross P. ostti ‘FenDanBai’ × P. × suffruticosa ‘HongQiao’, to identify sufficient high-quality markers for the construction of high-density genetic linkage map in tree peonies. After SLAF sequencing, a total of 78 Gb sequencing data and 285,403,225 pair-end reads were generated. We detected 309,198 high-quality SLAFs from these data, of which 85,124 (27.5%) were polymorphic. Subsequently, 3518 of the polymorphic markers, which were successfully encoded in to Mendelian segregation types, and were in conformity with the criteria of high-quality markers, were defined as effective markers and used for genetic linkage mapping. Finally, we constructed an integrated genetic map, which comprised 1189 markers on the five linkage groups, and spanned 920.699 centiMorgans (cM) with an average inter-marker distance of 0.774 cM. There were 1115 ‘SNP-only’ markers, 18 ‘InDel-only’ markers, and 56 ‘SNP&InDel’ markers on the map. Among these markers, 450 (37.85%) showed significant segregation distortion (P < 0.05). In conclusion, this investigation reported the first large-scale marker development and high-density linkage map construction for tree peony. The results of this study will serve as a solid foundation not only for marker-assisted breeding, but also for genome sequence assembly for tree peony. PMID:26010095

  13. Effects of inflorescence stem structure and cell wall components on the mechanical strength of inflorescence stem in herbaceous peony.

    PubMed

    Zhao, Daqiu; Han, Chenxia; Tao, Jun; Wang, Jing; Hao, Zhaojun; Geng, Qingping; Du, Bei

    2012-01-01

    Herbaceous peony (Paeonia lactiflora Pall.) is a traditional famous flower, but its poor inflorescence stem quality seriously constrains the development of the cut flower. Mechanical strength is an important characteristic of stems, which not only affects plant lodging, but also plays an important role in stem bend or break. In this paper, the mechanical strength, morphological indices and microstructure of P. lactiflora development inflorescence stems were measured and observed. The results showed that the mechanical strength of inflorescence stems gradually increased, and that the diameter of inflorescence stem was a direct indicator in estimating mechanical strength. Simultaneously, with the development of inflorescence stem, the number of vascular bundles increased, the vascular bundle was arranged more densely, the sclerenchyma cell wall thickened, and the proportion of vascular bundle and pith also increased. On this basis, cellulose and lignin contents were determined, PlCesA3, PlCesA6 and PlCCoAOMT were isolated and their expression patterns were examined including PlPAL. The results showed that cellulose was not strictly correlated with the mechanical strength of inflorescence stem, and lignin had a significant impact on it. In addition, PlCesA3 and PlCesA6 were not key members in cellulose synthesis of P. lactiflora and their functions were also different, but PlPAL and PlCCoAOMT regulated the lignin synthesis of P. lactiflora. These data indicated that PlPAL and PlCCoAOMT could be applied to improve the mechanical strength of P. lactiflora inflorescence stem in genetic engineering. PMID:22606025

  14. Total glucosides of peony ameliorates Sjögren's syndrome by affecting Th1/Th2 cytokine balance

    PubMed Central

    WU, GUOLIN; WU, NAYUAN; LI, TIANYI; LU, WENWEN; YU, GUOYOU

    2016-01-01

    The present study aimed to investigate the molecular mechanisms underlying the effects of total glucosides of peony (TGP) in the treatment of Sjögren's syndrome (SS). A total of 40 mice with SS were evenly assigned into four groups, including: Control group; TGP group, receiving 1 mg TGP daily; hydroxychloroquine (HCQ) group, receiving 0.25 mg HCQ daily; and a combined group, receiving 1 mg TGP and 0.25 mg HCQ daily. After 8 weeks, quantitative polymerase chain reaction and an enzyme-linked immunosorbent assay were used to detect the levels of interferon-γ (IFN-γ), interleukin-4 (IL-4), Fas and FasL in each group of mice. In addition, immunohistochemical analysis was used to determine the expression levels of IFN-γ and IL-4. IFN-γ, IL-4, Fas and FasL levels were significantly increased in the control group compared with the other three groups (P<0.05). Furthermore, the expression levels of these factors were reduced in the combined group in comparison with the HCQ group (P<0.05). The ratios of IFN-γ to IL-4 were decreased in the TGP and combined groups compared with the control group (P<0.05). The present results indicate that TGP ameliorates SS by affecting the Th1/Th2 cytokine balance and decreasing the expression levels of IFN-γ, IL-4, Fas and FasL. Therefore, TGP may represent a potential novel therapeutic agent for the treatment of SS.

  15. Identification of miRNAs Responsive to Botrytis cinerea in Herbaceous Peony (Paeonia lactiflora Pall.) by High-Throughput Sequencing

    PubMed Central

    Zhao, Daqiu; Gong, Saijie; Hao, Zhaojun; Tao, Jun

    2015-01-01

    Herbaceous peony (Paeonia lactiflora Pall.), one of the world’s most important ornamental plants, is highly susceptible to Botrytis cinerea, and improving resistance to this pathogenic fungus is a problem yet to be solved. MicroRNAs (miRNAs) play an essential role in resistance to B. cinerea, but until now, no studies have been reported concerning miRNAs induction in P. lactiflora. Here, we constructed and sequenced two small RNA (sRNA) libraries from two B. cinerea-infected P. lactiflora cultivars (“Zifengyu” and “Dafugui”) with significantly different levels of resistance to B. cinerea, using the Illumina HiSeq 2000 platform. From the raw reads generated, 4,592,881 and 5,809,796 sRNAs were obtained, and 280 and 306 miRNAs were identified from “Zifengyu” and “Dafugui”, respectively. A total of 237 conserved and 7 novel sequences of miRNAs were differentially expressed between the two cultivars, and we predicted and annotated their potential target genes. Subsequently, 7 differentially expressed candidate miRNAs were screened according to their target genes annotated in KEGG pathways, and the expression patterns of miRNAs and corresponding target genes were elucidated. We found that miR5254, miR165a-3p, miR3897-3p and miR6450a might be involved in the P. lactiflora response to B. cinerea infection. These results provide insight into the molecular mechanisms responsible for resistance to B. cinerea in P. lactiflora. PMID:26393656

  16. Effects of Inflorescence Stem Structure and Cell Wall Components on the Mechanical Strength of Inflorescence Stem in Herbaceous Peony

    PubMed Central

    Zhao, Daqiu; Han, Chenxia; Tao, Jun; Wang, Jing; Hao, Zhaojun; Geng, Qingping; Du, Bei

    2012-01-01

    Herbaceous peony (Paeonia lactiflora Pall.) is a traditional famous flower, but its poor inflorescence stem quality seriously constrains the development of the cut flower. Mechanical strength is an important characteristic of stems, which not only affects plant lodging, but also plays an important role in stem bend or break. In this paper, the mechanical strength, morphological indices and microstructure of P. lactiflora development inflorescence stems were measured and observed. The results showed that the mechanical strength of inflorescence stems gradually increased, and that the diameter of inflorescence stem was a direct indicator in estimating mechanical strength. Simultaneously, with the development of inflorescence stem, the number of vascular bundles increased, the vascular bundle was arranged more densely, the sclerenchyma cell wall thickened, and the proportion of vascular bundle and pith also increased. On this basis, cellulose and lignin contents were determined, PlCesA3, PlCesA6 and PlCCoAOMT were isolated and their expression patterns were examined including PlPAL. The results showed that cellulose was not strictly correlated with the mechanical strength of inflorescence stem, and lignin had a significant impact on it. In addition, PlCesA3 and PlCesA6 were not key members in cellulose synthesis of P. lactiflora and their functions were also different, but PlPAL and PlCCoAOMT regulated the lignin synthesis of P. lactiflora. These data indicated that PlPAL and PlCCoAOMT could be applied to improve the mechanical strength of P. lactiflora inflorescence stem in genetic engineering. PMID:22606025

  17. Identification of miRNAs Responsive to Botrytis cinerea in Herbaceous Peony (Paeonia lactiflora Pall.) by High-Throughput Sequencing.

    PubMed

    Zhao, Daqiu; Gong, Saijie; Hao, Zhaojun; Tao, Jun

    2015-01-01

    Herbaceous peony (Paeonia lactiflora Pall.), one of the world's most important ornamental plants, is highly susceptible to Botrytis cinerea, and improving resistance to this pathogenic fungus is a problem yet to be solved. MicroRNAs (miRNAs) play an essential role in resistance to B. cinerea, but until now, no studies have been reported concerning miRNAs induction in P. lactiflora. Here, we constructed and sequenced two small RNA (sRNA) libraries from two B. cinerea-infected P. lactiflora cultivars ("Zifengyu" and "Dafugui") with significantly different levels of resistance to B. cinerea, using the Illumina HiSeq 2000 platform. From the raw reads generated, 4,592,881 and 5,809,796 sRNAs were obtained, and 280 and 306 miRNAs were identified from "Zifengyu" and "Dafugui", respectively. A total of 237 conserved and 7 novel sequences of miRNAs were differentially expressed between the two cultivars, and we predicted and annotated their potential target genes. Subsequently, 7 differentially expressed candidate miRNAs were screened according to their target genes annotated in KEGG pathways, and the expression patterns of miRNAs and corresponding target genes were elucidated. We found that miR5254, miR165a-3p, miR3897-3p and miR6450a might be involved in the P. lactiflora response to B. cinerea infection. These results provide insight into the molecular mechanisms responsible for resistance to B. cinerea in P. lactiflora. PMID:26393656

  18. A new steroidal glycoside from Corypha taliera Roxb., a globally endangered species.

    PubMed

    Shoeb, Mohammad; Khondker, Moniruzzaman; Nahar, Nilufar

    2016-02-01

    The reversed-phased HPLC analysis of the methanol extract of the pericarp of C. taliera Roxb. (Talipalm), a rare species of Arecaceae family, afforded a new steroidal glycoside, ?-sitosterol-3-O-?-l-rhamnopyranosyl-(1?4)-?-d-xylopyranosyl-(1?4)-?-d-glucopyranosyl-(1?4)-?-d-glucopyranoside (1). The structure of the compound was elucidated unequivocally by UV, IR, HR-ESI-MS, (1)H and (13)C NMR spectroscopic studies. PMID:26196451

  19. Two phenylpropanoid glycosides from Leonurus glaucescens.

    PubMed

    Cali?, I; Ersz, T; Ta?demir, D; Redi, P

    1992-01-01

    Two new phenylpropanoid glycosides, leonosides A and B, and two known glycosides lavandulifolioside and verbascoside, were isolated from the aerial parts of Leonurus glaucescens. On the basis of chemical and spectral evidence, leonosides A and B were shown to be beta-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-arabinopyranosyl-(1---- 2)-alpha-L- rhamnopyranosyl-(1----3)-4-O-feruloyl-beta-D-glucopyranoside and beta-(3-hydroxy, 4-methoxyphenyl)-ethyl-O-alpha-L-arabinopyranosyl-(1----2)- alpha-L-rhamnopyranosyl-(1----3)-4-O-feruloyl-beta-D-glucopyranosi de, respectively. PMID:1367886

  20. Chalcone and flavonol glycosides from Asarum canadense (Aristolochiaceae).

    PubMed

    Iwashina, T; Kitajima, J

    2000-12-01

    Two chalcone glycosides were isolated, together with seven known flavonol glycosides, from the leaves of Asarum canadense. The structures of the chalcone glycosides were established as chalcononaringenin 2',4'-di-O-glucoside and chalcononaringenin 2'-O-glucoside-4'-O-gentiobioside by chemical, UV, FAB MS, 1H and 13C NMR evidence. PMID:11140534

  1. Two new phenolic glycosides from Syringa reticulata.

    PubMed

    Machida, Koichi; Ohkawa, Naomi; Ohsawa, Asami; Kikuchi, Masao

    2009-04-01

    Two new phenolic glycosides-3'-O-beta-D: -glucopyranosysalidroside (1) and cis-echinacoside (2)-together with four known ones-forsythoside B (3), decaffeoylacteoside (4), osmanthuside F (5) and (-)-olivil-4'-O-beta-D: -glucopyranoside (6)-were isolated from the leaves of Syringa reticulata. Their structures were established on the basis of spectral and chemical data. PMID:18985282

  2. A new isoflavone glycoside from Pueraria alopecuroides.

    PubMed

    Yang, Junlin; Fan, Qingfei; Zhang, Huanli; Song, Qishi

    2016-01-01

    A new isoflavone glycoside, (-)-tuberosin-3-O-?-D-glucopyranoside (1), along with 10 known compounds 1a-10, was isolated from Pueraria alopecuroides. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS. These compounds were isolated from this plant for the first time. PMID:26525177

  3. ALTERNANSUCRASE ACCEPTOR REACTIONS WITH METHYL GLYCOSIDES

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Alternansucrase (EC 2.4.1.140) is a D-glucansucrase that synthesizes an alternating alpha-(1-3), (1-6)-linked D-glucan from sucrose. It also synthesizes oligosaccharides via D-glucopyranosyl transfer to various acceptor sugars. We have studied the acceptor products arising from methyl glycosides a...

  4. Chlorination diversifies Cimicifuga racemosa triterpene glycosides.

    PubMed

    Chen, Shao-Nong; Lankin, David C; Nikolic, Dejan; Fabricant, Daniel S; Lu, Zhi-Zhen; Ramirez, Benjamin; van Breemen, Richard B; Fong, Harry H S; Farnsworth, Norman R; Pauli, Guido F

    2007-06-01

    Extracts from the roots and rhizomes of black cohosh (Cimicifuga racemosa) are widely used as dietary supplements to alleviate menopausal symptoms. State-of-the-art quality control measures involve phytochemical fingerprinting of the triterpene glycosides for species identification and chemical standardization by HPLC. In the course of developing materials and methods for standardization procedures, the major C. racemosa triterpene glycoside (1) was isolated and initially thought to be cimicifugoside (2). Detailed HR-LC-MS and 1D and 2D NMR analysis of 1 and 2 unambiguously revealed that 1 is the chlorine-containing derivative of 2, namely, 25-chlorodeoxycimigenol-3-O-beta-d-xyloside. Accordingly, HPLC profiles of black cohosh preparations require revision of the assignments of the chlorinated (1) and nonchlorinated (2) pair. Besides explaining the substantial shift in polarity (DeltatR[RP-18] ca. 20 min), 25-deoxychlorination opens a new pathway of structural diversification in triterpene glycoside chemistry. As chemical conversion of 2 into 1 could be demonstrated, deoxychlorination may be interpreted as artifact formation. Simultaneously, however, it is a potentially significant pathway for the gastric in vivo conversion ("nature's prodrug") of the relatively polar triterpene glycosides into significantly less polar chlorinated derivatives with altered pharmacological properties. PMID:17555351

  5. Twisting of glycosidic bonds by hydrolases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Patterns of scissile bond twisting have been found in crystal structures of glycoside hydrolases (GHs) that are complexed with substrates and inhibitors. To estimate the increased potential energy in the substrates that results from this twisting, we have plotted torsion angles for the scissile bond...

  6. Flavone C-glycosides from Anthurium andraeanum.

    PubMed

    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). PMID:22816298

  7. Transcriptomic Analysis of the Underground Renewal Buds during Dormancy Transition and Release in ‘Hangbaishao’ Peony (Paeonia lactiflora)

    PubMed Central

    Zhang, Jiaping; Wang, Guanqun; Li, Xin; Xia, Yiping

    2015-01-01

    Paeonia lactiflora is one of the most famous species of herbaceous peonies with gorgeous flowers. Bud dormancy is a crucial developmental process that allows P. lactiflora to survive unfavorable environmental conditions. However, little information is available on the molecular mechanism of the bud dormancy in P. lactiflora. We performed de novo transcriptome sequencing using the Illumina RNA sequencing platform for the underground renewal buds of P. lactiflora ‘Hangbaishao’ to study the molecular mechanism underlying its bud dormancy transition (the period from endodormancy to ecodormancy) and release (the period from ecodormancy to bud elongation and sprouting). Approximately 300 million high-quality clean reads were generated and assembled into 207,827 (mean length = 828 bp) and 51,481 (mean length = 1250 bp) unigenes using two assembly methods named “Trinity” and “Trinity+PRICE”, respectively. Based on the data obtained by the latter method, 32,316 unigenes were annotated by BLAST against various databases. Approximately 1,251 putative transcription factors were obtained, of which the largest number of unique transcripts belonged to the basic helix-loop-helix protein (bHLH) transcription factor family, and five of the top ten highly expressed transcripts were annotated as dehydrin (DHN). A total of 17,705 simple sequence repeat (SSR) motifs distributed in 13,797 sequences were obtained. The budbreak morphology, levels of indole-3-acetic acid (IAA) and abscisic acid (ABA), and activities of guaiacol peroxidase (POD) and catalase (CAT) were observed. The expression of 20 interested unigenes, which annotated as DHN, heat shock protein (HSP), histone, late elongated hypocotyl (LHY), and phytochrome (PHY), and so on, were also analyzed. These studies were based on morphological, physiological, biochemical, and molecular levels and provide comprehensive insight into the mechanism of dormancy transition and release in P. lactiflora. Transcriptome dataset can be highly valuable for future investigation on gene expression networks in P. lactiflora as well as research on dormancy in other non-model perennial horticultural crops of commercial significance. PMID:25790307

  8. Enzymatic Processing of Bioactive Glycosides from Natural Sources

    NASA Astrophysics Data System (ADS)

    Weignerová, Lenka; Křen, Vladimír

    A number of biologically active natural products are glycosides. Often, the glycosidic residue is crucial for their activity. In other cases, glycosylation only improves their pharmacokinetic parameters. Enzymatic modification of these glycosides - both extension of the glycoside moiety and its selective trimming - is advantageous due to their selectivity and mildness of the reaction conditions in the presence of reactive and sensitive complex aglycones. Enzymatic reactions enable the resulting products to be used as "natural products", e.g., in nutraceuticals. This chapter concentrates on naturally occurring glycosides used in medicine but also in the food and flavor industry (e.g., sweeteners). Both "classical" and modern methods will be discussed.

  9. Efficiency of transcellular transport and efflux of flavonoids with different glycosidic units from flavonoids of Litsea coreana L. in a MDCK epithelial cell monolayer model.

    PubMed

    Chen, Zhaolin; Ma, Taotao; Huang, Cheng; Zhang, Lei; Zhong, Jian; Han, Jingwen; Hu, Tingting; Li, Jun

    2014-03-12

    Although there is strong evidence to suggest that beneficial effects of the flavonoids in human health, the extent to which flavonoids are absorbed and the mechanisms involved are controversial. The objective of this study was to determine the bi-directional permeability and efflux characters of the four main flavonoids with different glycosidic units isolated from flavonoids of Litsea coreana L. and to discuss the transport mechanisms using the epithelial cell model MDCK. The transport of the four main flavonoid glycosides at concentration of 40, 80, 160 ?M was concentration-dependent in both apical to basolateral and the reverse direction. Contemporary, the influx and efflux of the flavonoid glycosides were temperature-dependent and pH-dependent at concentration of 80 ?M, and transport of flavonoid glycosides was obviously decreased when experiments performed in the presence of 1mM sodium azide (an ATP inhibitor). Uptake of quercetin-3-O-?-D-glucoside or kaempferol-3-O-?-D-glucoside was inhibited by 50 ?M phloridzin, a specific and competitive inhibitor of SGLT. Moreover, the flavonoids exhibited significantly larger basolateral to apical Papp than that of the reverse direction, suggesting the existence of efflux mechanisms. The 50 ?M verapamil, a chemical inhibitor of P-glycoprotein (P-gp), had no effect on the transport of four flavonoid glycosides. However, 50 ?M MK-571 or 1 mM probenecid, MRP2 inhibitors, led to an apparently decrease in the efflux of flavonoid glycosides. Therefore, MRP2 but P-gp may be involved in the transport of the four flavonoid glycosides. Taken together, the experimental observations in our study provide useful information for pharmacological applications of flavonoids with different glycosidic units from flavonoids of L. coreana L. PMID:24365259

  10. Micro/Nano hierarchical peony-like Al doped ZnO superhydrophobic film: The guiding effect of (100) preferred seed layer

    PubMed Central

    Li, Yang; Wang, Jingfeng; Kong, Yi; Zhou, Jia; Wu, Jinzhu; Wang, Gang; Bi, Hai; Wu, Xiaohong; Qin, Wei; Li, Qingkun

    2016-01-01

    In this communication, we present a versatile and controllable strategy for formation of superhydrophobic micro/nano hierarchical Al doped ZnO (AZO) films with a water contact angle (CA) of 170 ± 4°. This strategy involves a two-step layer-by-layer process employing an atomic layer deposition (ALD) technique followed by a hydrothermal method, and the resulting novel AZO surface layer consists of (100) dominant nano-rice-like AZO seed layer (the water CA of 110 ± 4°) covered with micro-peony-like AZO top. The growth mechanisms and superhydrophobic properties of the hierarchical AZO layer are discussed. It is believed that the present route holds promise for future success in the design and development of practical superhydrophobic materials. PMID:26753877

  11. Micro/Nano hierarchical peony-like Al doped ZnO superhydrophobic film: The guiding effect of (100) preferred seed layer

    NASA Astrophysics Data System (ADS)

    Li, Yang; Wang, Jingfeng; Kong, Yi; Zhou, Jia; Wu, Jinzhu; Wang, Gang; Bi, Hai; Wu, Xiaohong; Qin, Wei; Li, Qingkun

    2016-01-01

    In this communication, we present a versatile and controllable strategy for formation of superhydrophobic micro/nano hierarchical Al doped ZnO (AZO) films with a water contact angle (CA) of 170 ± 4°. This strategy involves a two-step layer-by-layer process employing an atomic layer deposition (ALD) technique followed by a hydrothermal method, and the resulting novel AZO surface layer consists of (100) dominant nano-rice-like AZO seed layer (the water CA of 110 ± 4°) covered with micro-peony-like AZO top. The growth mechanisms and superhydrophobic properties of the hierarchical AZO layer are discussed. It is believed that the present route holds promise for future success in the design and development of practical superhydrophobic materials.

  12. Alleviating coking in ethanol steam reforming by co-loading binary oxides Ni-M (M=Ag, Cu, Mn) on peony-like ceria

    NASA Astrophysics Data System (ADS)

    Xian, C. N.; Li, J. G.; Li, H.; Chen, L. Q.; Sun, J.; Lee, J. S.

    2011-06-01

    Previously, hydrothermally prepared mesoporous peony-like ceria (PCO) material was shown to exhibit superior catalytic properties for CO oxidation and ethanol reforming. Ni supported PCO had been shown to have high activity for ethanol steam reforming at low temperature. In this work, Ag, Cu and Mn is co-loaded with Ni on PCO catalysts by impregnation method. The catalysts were studied by X-ray diffraction (XRD), scanning electron microscopy (SEM), and a combined thermogravimetry, differential scanning calorimetry, and mass spectrometry (TG-DSC-MS). It was found that all the catalysts gave 100% ethanol conversion above ca. 300C and exhibited similar H2 yield. It is found that the severe coking problem for the Ni-loaded PCO catalyst was alleviated significantly if Ag, Cu or Mn is co-loaded. Among them, the addition of Mn is the most effective in reducing carbon formation.

  13. Micro/Nano hierarchical peony-like Al doped ZnO superhydrophobic film: The guiding effect of (100) preferred seed layer.

    PubMed

    Li, Yang; Wang, Jingfeng; Kong, Yi; Zhou, Jia; Wu, Jinzhu; Wang, Gang; Bi, Hai; Wu, Xiaohong; Qin, Wei; Li, Qingkun

    2016-01-01

    In this communication, we present a versatile and controllable strategy for formation of superhydrophobic micro/nano hierarchical Al doped ZnO (AZO) films with a water contact angle (CA) of 170 ± 4°. This strategy involves a two-step layer-by-layer process employing an atomic layer deposition (ALD) technique followed by a hydrothermal method, and the resulting novel AZO surface layer consists of (100) dominant nano-rice-like AZO seed layer (the water CA of 110 ± 4°) covered with micro-peony-like AZO top. The growth mechanisms and superhydrophobic properties of the hierarchical AZO layer are discussed. It is believed that the present route holds promise for future success in the design and development of practical superhydrophobic materials. PMID:26753877

  14. An inverting β-1,2-mannosidase belonging to glycoside hydrolase family 130 from Dyadobacter fermentans.

    PubMed

    Nihira, Takanori; Chiku, Kazuhiro; Suzuki, Erika; Nishimoto, Mamoru; Fushinobu, Shinya; Kitaoka, Motomitsu; Ohtsubo, Ken'ichi; Nakai, Hiroyuki

    2015-11-30

    The glycoside hydrolase family (GH) 130 is composed of inverting phosphorylases that catalyze reversible phosphorolysis of β-D-mannosides. Here we report a glycoside hydrolase as a new member of GH130. Dfer_3176 from Dyadobacter fermentans showed no synthetic activity using α-D-mannose 1-phosphate but it released α-D-mannose from β-1,2-mannooligosaccharides with an inversion of the anomeric configuration, indicating that Dfer_3176 is a β-1,2-mannosidase. Mutational analysis indicated that two glutamic acid residues are critical for the hydrolysis of β-1,2-mannotriose. The two residues are not conserved among GH130 phosphorylases and are predicted to assist the nucleophilic attack of a water molecule in the hydrolysis of the β-D-mannosidic bond. PMID:26476324

  15. ?-cyclodextrin assistant flavonoid glycosides enzymatic hydrolysis

    PubMed Central

    Jin, Xin; Zhang, Zhen-hai; Sun, E.; Jia, Xiao-Bin

    2013-01-01

    Background: The content of icaritin and genistein in herba is very low, preparation with relatively large quantities is an important issue for extensive pharmacological studies. Objective: This study focuses on preparing and enzymic hydrolysis of flavonoid glycosides /?-cyclodextrin inclusion complex to increase the hydrolysis rate. Materials and Methods: The physical property of newly prepared inclusion complex was tested by differential scanning calorimetry (DSC). The conditions of enzymatic hydrolysis were optimized for the bioconversion of flavonoid glycosides /?-cyclodextrin inclusion complex by mono-factor experimental design. The experiments are using the icariin and genistein as the model drugs. Results: The solubility of icariin and genistein were increased almost 17 times from 29.2 ?g/ml to 513.5 ?g/ml at 60C and 28 times from 7.78 ?g/ml to 221.46 ?g/ml at 50C, respectively, demonstrating that the inclusion complex could significantly increase the solubility of flavonoid glycosides. Under the optimal conditions, the reaction time of icariin and genistin decreased by 68% and 145%, when compared with that without ?-CD inclusion. By using this enzymatic condition, 473 mg icaritin (with the purity of 99.34%) and 567 mg genistein(with the purity of 99.46%), which was finally determined by melt point, ESI-MS, UV, IR, 1H NMR and 13C NMR, was obtained eventually by transforming the inclusion complex(contains 1.0 g substrates). Conclusion: This study can clearly indicate a new attempt to improve the speed of enzyme-hydrolysis of poorly water-soluble flavonoid glycosides and find a more superior condition which is used to prepare icaritin and genistein. PMID:24143039

  16. ent-Kaurene Glycosides from Ageratina cylindrica.

    PubMed

    Bustos-Brito, Celia; Sánchez-Castellanos, Mariano; Esquivel, Baldomero; Calderón, José S; Calzada, Fernando; Yépez-Mulia, Lilian; Joseph-Nathan, Pedro; Cuevas, Gabriel; Quijano, Leovigildo

    2015-11-25

    The aqueous extract of the leaves of Ageratina cylindrica afforded six new ent-kaurenoic acid glycosides together with the known diterpenoid paniculoside V, the flavonoid astragalin, chlorogenic acid, and L-chiro-inositol. The structures were elucidated mainly by NMR and MS methods, and the absolute configuration was established by vibrational circular dichroism spectroscopy. The new compounds showed moderate antiprotozoal activity against Entamoeba histolytica and Giardia lamblia trophozoites. PMID:26517282

  17. New pregnane glycosides from Gymnema sylvestre.

    PubMed

    Xu, Rui; Yang, Yu; Zhang, Yang; Ren, Fengxia; Xu, Jinlong; Yu, Nengjiang; Zhao, Yimin

    2015-01-01

    Four new pregnane glycosides 1-4 were isolated from the ethanol extract of the stem of Gymnema sylvestre and named gymsylvestrosides A-D. Hydrolysis of compound 1 under the catalysis of Aspergilus niger ?-glucosidase afforded compound 5 (gymsylvestroside E). Their structures were determined by spectroscopic methods such as HRESIMS, 1D and 2D NMR, as well as HMQC-TOCSY experiment. Compounds 1-4 were screened for Saccharomyces cerevisiae ?-glucosidase inhibitory activity. PMID:25685911

  18. A New Cucurbitane Glycoside from Siraitia grosvenorii.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Meneni, Srinivasa Rao

    2015-09-01

    A systematic phytochemical study of the commercial extract of Luo Han Guo (Siraitia grosvenorii) resulted in the isolation of an additional minor new cucurbitane glycoside, mogroside V Al (1). The structure of the new compound was characterized on the basis of 1D (1H and 13C NMR) and 2D (COSY, HMQC, HMBC and NOESY) NMR and high resolution mass spectral (HRMS) data, as well as hydrolysis studies. PMID:26594748

  19. Alkyl and phenolic glycosides from Saussurea stella.

    PubMed

    Wang, Tian-Min; Wang, Ru-Feng; Chen, Hu-Biao; Shang, Ming-Ying; Cai, Shao-Qing

    2013-07-01

    One alkyl glycoside, saussurostelloside A (1), two phenolic glycosides, saussurostellosides B1 (2) and B2 (3), and 27 known compounds, including eleven flavonoids, seven phenolics, six lignans, one neolignan, one phenethyl glucoside and one fatty acid, were isolated from an ethanol extract of Saussurea stella (Asteraceae). Their structures were elucidated by NMR, MS, UV, and IR spectroscopic analysis. Of the known compounds, (+)-medioresinol-di-O-?-D-glucoside (7), picraquassioside C (10), and diosmetin-3'-O-?-D-glucoside (27) were isolated from the Asteraceae family for the first time, while (+)-pinoresinol-di-O-?-D-glucoside (6), di-O-methylcrenatin (11), protocatechuic acid (14), 1,5-di-O-caffeoylquinic acid (17), formononetin (28), and phenethyl glucoside (29) were isolated from the Saussurea genus for the first time. The anti-inflammatory activities of three new compounds (1-3), five lignans ((-)-arctiin (4), (+)-pinoresinol-4-O-?-D-glucoside (5), (+)-pinoresinol-di-O-?-D-glucoside (6), (+)-medioresinol-di-O-?-D-glucoside (7) and (+)-syringaresinol-4-O-?-D-glucoside (8)), one neolignan (picraquassioside C (10)), and one phenolic glycoside (di-O-methylcrenatin (11)) were evaluated by testing their inhibition of the release of ?-glucuronidase from PAF-stimulated neutrophils. Only compound 5 showed moderate inhibition of the release of ?-glucuronidase, with an inhibition ratio of 39.1%. PMID:23567860

  20. The Identification of Perillyl Alcohol Glycosides with Improved Antiproliferative Activity

    PubMed Central

    2015-01-01

    A facile route to perillyl alcohol (POH) differential glycosylation and the corresponding synthesis of a set of 34 POH glycosides is reported. Subsequent in vitro studies revealed a sugar dependent antiproliferative activity and the inhibition of S6 ribosomal protein phosphorylation as a putative mechanism of representative POH glycosides. The most active glycoside from this cumulative study (4?-azido-d-glucoside, PG9) represents one of the most cytotoxic POH analogues reported to date. PMID:25121720

  1. Steroidal glycosides from the underground parts of Solanum sodomaeum.

    PubMed

    Ono, Masateru; Nishimura, Kazuya; Suzuki, Keita; Fukushima, Takeshi; Igoshi, Keiji; Yoshimitsu, Hitoshi; Ikeda, Tsuyoshi; Nohara, Toshihiro

    2006-02-01

    A new steroidal glycoside has been isolated from the underground parts of Solanum sodomaeum L., along with seven known steroidal glycosides. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence, and the structure of one known pregnane type glycoside was corrected. In addition, their antiproliferative activity against human promyelocytic leukemia (HL-60) cells was investigated, and five compounds exhibited stronger activity than cisplatin. PMID:16462070

  2. [Phenylethanoid glycosides distribution in medicinal plants of Gesneriaceae].

    PubMed

    Bai, Zhen-Fang; Wang, Xiao-Qin; Xiao, Pei-Gen; Liu, Yong

    2013-12-01

    To investigate the role of distribution and phylogeny of phenylethanoid glycoside in medicinal plants of Gesneriaceae, five phenylpropanoid glycosides, acteoside, paraboside B, isonuomioside A, paraboside II, and paraboside III were quantitatively determined in 12 species of Gesneriaceae by HPLC. The existence and content of these compounds were analyzed. The results showed that phenylethanoid glycosides were found in the most of those plants, but the kind of phenylethanoid glycosides varied in different species. Acteoside distribute in most of this plant group, paraboside B, isonuomioside A, paraboside II, and paraboside III were rare in those plants. The results of this study support morphological viewpoint that Trib. Trichosporeae is more developmental than Trib. Didymocarpeae. PMID:24791528

  3. Sesquiterpenoid tropolone glycosides from Liriosma ovata.

    PubMed

    Ma, Jun; Pawar, Rahul S; Grundel, Erich; Mazzola, Eugene P; Ridge, Clark D; Masaoka, Takashi; Le Grice, Stuart F J; Wilson, Jennifer; Beutler, John A; Krynitsky, Alexander J

    2015-02-27

    Two new sesquiterpenoid tropolone glycosides, liriosmasides A (1) and B (2), along with two known compounds, secoxyloganin and oplopanpheside C, were isolated from a methanol extract of the roots of Liriosma ovata. The structures of 1 and 2 were elucidated by spectroscopic methods including 1D and 2D NMR and by high-resolution mass spectrometry involving an ultra-high-performance liquid chromatography-quadrupole-orbital ion trap mass spectrometric (UHPLC-Q-Orbitrap MS) method. Compound 1 showed weak inhibitory activity against HIV RNase H. PMID:25587934

  4. Syntheses of dopa glycosides using glucosidases.

    PubMed

    Sivakumar, Ramaiah; Ponrasu, Thangavel; Divakar, Soundar

    2009-02-01

    Syntheses of L: -dopa 1a glucoside 10a,b and DL: -dopa 1b glycosides 10-18 with D: -glucose 2, D: -galactose 3, D: -mannose 4, D: -fructose 5, D: -arabinose 6, lactose 7, D: -sorbitol 8 and D: -mannitol 9 were carried out using amyloglucosidase from Rhizopus mold, beta-glucosidase isolated from sweet almond and immobilized beta-glucosidase. Invariably, L: -dopa and DL: -dopa gave low to good yields of glycosides 10-18 at 12-49% range and only mono glycosylated products were detected through glycosylation/arylation at the third or fourth OH positions of L: -dopa 1a and DL: -dopa 1b. Amyloglucosidase showed selectivity with D: -mannose 4 to give 4-O-C1beta and D: -sorbitol 8 to give 4-O-C6-O-arylated product. beta-Glucosidase exhibited selectivity with D: -mannose 4 to give 4-O-C1beta and lactose 7 to give 4-O-C1beta product. Immobilized beta-glucosidase did not show any selectivity. Antioxidant and angiotensin converting enzyme inhibition (ACE) activities of the glycosides were evaluated glycosides, out of which L: -3-hydroxy-4-O-(beta-D: -galactopyranosyl-(1'-->4)beta-D: -glucopyranosyl) phenylalanine 16 at 0.9 +/- 0.05 mM and DL: -3-hydroxy-4-O-(beta-D: -glucopyranosyl) phenylalanine 11b,c at 0.98 +/- 0.05 mM showed the best IC(50) values for antioxidant activity and DL: -3-hydroxy-4-O-(6-D: -sorbitol)phenylalanine 17 at 0.56 +/- 0.03 mM, L: -dopa-D: -glucoside 10a,b at 1.1 +/- 0.06 mM and DL: -3-hydroxy-4-O-(D: -glucopyranosyl)phenylalanine 11a-d at 1.2 +/- 0.06 mM exhibited the best IC(50) values for ACE inhibition. PMID:18712474

  5. Two new triterpenoid glycosides from Cyclocarya paliurus.

    PubMed

    Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhou, Jun; Qiu, Sheng-Xiang; Chen, Ji-Jun

    2006-01-01

    Two new dammarane triterpenoid glycosides named cyclocarosides B (1) and C (2) were isolated from the leaves of Cyclocarya paliurus. Based on FAB-MS, HRESI-MS, IR, 1H NMR, 13C NMR, and 2D-NMR (HMQC, HMBC, COSY, ROESY) data, the structures of cyclocarosides B (1) and C (2) were elucidated as (20S,24R)-epoxydammarane (3beta,12beta)-25-hydroxyl-12-O-beta-D-quinovopyranosyl-3-O-beta-D-quinovopyranoside (1), and (20S,24R)-epoxydammarane (3beta, 12beta)-25-hydroxyl-12-O-alpha-L-arabinopyranosyl-3-O-(5'-O-acetyl)-alpha-L-arabinofuranoside (2). PMID:16753788

  6. Two pentasaccharide resin glycosides from Argyreia acuta.

    PubMed

    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. PMID:25925631

  7. Acetophenone glycosides from thyme (Thymus vulgaris L.).

    PubMed

    Wang, M; Kikuzaki, H; Lin, C C; Kahyaoglu, A; Huang, M T; Nakatani, N; Ho, C T

    1999-05-01

    Four acetophenone glycosides were isolated from the butanol-soluble fraction of thyme extracts. Their structures were determined by spectral methods (MS, NMR, and 2D-NMR). Among them, two new compounds, 4-hydroxyacetophenone 4-O-[5-O-(3, 5-dimethoxy-4-hydroxybenzoyl)-beta-D-apiofuranosyl]-(1-->2)-beta-D -gl ucopyranoside (1) and 4-hydroxyacetophenone 4-O-[5-O-(4-hydroxybenzoyl)-beta-D-apiofuranosyl]-(1-->2)-beta-D-+ ++gluc opyranoside (2), were determined. Compound 1 showed weak cytotoxicity, inhibiting DNA synthesis of human leukemia cells. PMID:10552470

  8. Deuterium NMR Investigation of the lyotropic phases of alkyl ?-glycoside/D2O systems.

    PubMed

    Misran, Omar; Timimi, Bakir A; Heidelberg, Thorsten; Sugimura, Akihiko; Hashim, Rauzah

    2013-06-20

    We have investigated the phase behavior of four glycosides (?C8OGlc, ?C8SGlc, ?C10OGlc, ?C8OGal) 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 (?C10OGlc) 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 (?C8OGlc and ?C8OGal) and the lamellar phase (?C8SGlc and ?C10OGlc). 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-?-glucoside and ?-galactoside, which show the presence of strong intralayer hydrogen bonding. PMID:23718628

  9. Phytosteryl glycosides reduce cholesterol absorption: mechanisms in mice

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Phytosteryl glycosides occur in natural foods but little is known about their metabolism and bioactivity. Purified acylated steryl glycosides (ASG) were compared with phytosteryl esters (PSE) in mice. Animals on a phytosterol-free diet received ASG or PSE by gavage in purified soybean oil along with...

  10. Enzymatic hydrolysis of steryl ferulates and steryl glycosides

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Steryl ferulates and steryl glycosides are phytosterol conjugates found characteristically in cereals. Their properties in enzymatic hydrolysis are, however, not yet well known. Steryl ferulates and steryl glycosides were extracted and purified from rye and wheat bran. Their rates of hydrolysis with...

  11. Evaluating the Cancer Therapeutic Potential of Cardiac Glycosides

    PubMed Central

    Caldern-Montao, Jos Manuel; Burgos-Morn, Estefana; Orta, Manuel Luis; Maldonado-Navas, Dolores; Garca-Domnguez, Irene; Lpez-Lzaro, Miguel

    2014-01-01

    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. PMID:24895612

  12. Antiproliferative cardiac glycosides from the latex of Antiaris toxicaria.

    PubMed

    Liu, Qian; Tang, Jin-Shan; Hu, Meng-Jie; Liu, Jie; Chen, Hai-Feng; Gao, Hao; Wang, Guang-Hui; Li, Shun-Lin; Hao, Xiao-Jiang; Zhang, Xiao-Kun; Yao, Xin-Sheng

    2013-09-27

    Phytochemical investigation of the latex of Antiaris toxicaria resulted in the isolation of 15 new [antiarosides J-X (1-15)] and 17 known cardiac glycosides. The effects of the cardiac glycosides on apoptosis and the expression of orphan nuclear receptor Nur77 were examined in human NIH-H460 lung cancer cells. Several of the cardiac glycosides induced apoptosis in lung cancer cells, which was accompanied by induction of Nur77 protein expression. Treatment of cancer cells with the cardiac glycosides resulted in translocation of the Nur77 protein from the nucleus to the cytoplasm and subsequent targeting to mitochondria. The results show that the cardiac glycosides exert their apoptotic effect through the Nur77-dependent apoptotic pathway. PMID:24033101

  13. Antitrypanosomal cycloartane glycosides from Astragalus baibutensis.

    PubMed

    Cali?, Ihsan; Koyuno?lu, Semra; Ye?ilada, Akgl; Brun, Reto; Redi, Peter; Ta?demir, Deniz

    2006-08-01

    Baibutoside (5), a new cycloartane-type triterpene glycoside, has been isolated from the roots of Astragalus baibutensis along with four known glycosides, acetylastragaloside I (1), and astragalosides I, II, and IV (2-4, resp.). The structure elucidation of the compounds were achieved by a combination of one- and two-dimensional NMR techniques (DQF-COSY, HSQC, HMBC, and ROESY), and mass spectrometry (ESI-MS), where all the compounds were shown to have cycloastragenol (=(20R,24S)-3beta,6alpha,16beta,25-tetrahydroxy-20,24-epoxy-9,19-cyclolanostane) as aglycone. All compounds were tested for in vitro antiprotozoal activity. Compounds 1-4 displayed notable activity vs. Trypanosoma brucei rhodesiense, with acetylastragaloside I (1) being the most potent (IC50 9.5 microg/ml). Acetylastragaloside I (1) was also lethal to T. cruzi (IC50 5.0 microg/ml), and it is the first cycloartane-type triterpene with remarkable trypanocidal activity against both T. brucei rhodesiense and T. cruzi. However, it exhibits some cytotoxicity on mammalian cells. PMID:17193323

  14. Localization and catabolism of cyanogenic glycosides.

    PubMed

    Poulton, J E

    1988-01-01

    The catabolism of cyanogenic glycosides is initiated by cleavage of the carbohydrate moiety by one or more beta-glycosidases, which yields the corresponding alpha-hydroxynitrile. Until recently, the mode by which cyanogenic disaccharides are hydrolysed was largely unclear. Investigation of highly purified beta-glycosidases from plants containing cyanogenic disaccharides has now indicated that these compounds may be degraded via two distinct pathways, depending on the plant species. beta-Glycosidases from Davallia trichomanoides and Vicia angustifolia hydrolysed (R)-vicianin and (R)-amygdalin at the aglycone-disaccharide bond producing mandelonitrile and the corresponding disaccharide. Alternatively, hydrolysis of cyanogenic disaccharides in Prunus serotina, almonds, and Linum usitatissimum involves stepwise removal of the sugar residues. The nature of these enzymes and of other beta-glycosidases responsible for hydrolysis of simple cyanogenic monosaccharides is discussed. Hydroxynitriles may decompose either spontaneously or enzymically in the presence of a hydroxynitrile lyase to produce hydrogen cyanide and an aldehyde or ketone. The major kinetic and molecular properties of hydroxynitrile lyases purified from species accumulating aromatic and aliphatic cyanogens are reviewed. Cyanogenesis occurs rapidly only after cyanogenic plant tissues are macerated, allowing glycosides access to their catabolic enzymes. The possible nature of the compartmentation which prevents cyanogenesis under normal physiological conditions is discussed in relation to our knowledge of the tissue and subcellular localizations of cyanogens and catabolic enzymes. PMID:3073063

  15. Documentation of reticulate evolution in peonies (Paeonia) using internal transcribed spacer sequences of nuclear ribosomal DNA: implications for biogeography and concerted evolution.

    PubMed Central

    Sang, T; Crawford, D J; Stuessy, T F

    1995-01-01

    The internal transcribed spacers (ITS) of nuclear ribosomal DNA of 33 species of genus Paeonia (Paeoniaceae) were sequenced. In section Paeonia, different patterns of nucleotide additivity were detected in 14 diploid and tetraploid species at sites that are variable in the other 12 species of the section, suggesting that reticulate evolution has occurred. Phylogenetic relationships of species that do not show additivity, and thus ostensibly were not derived through hybridization, were reconstructed by parsimony analysis. The taxa presumably derived through reticulate evolution were then added to the phylogenetic tree according to additivity from putative parents. The study provides an example of successfully using ITS sequences to reconstruct reticulate evolution in plants and further demonstrates that the sequence data could be highly informative and accurate for detecting hybridization. Maintenance of parental sequences in the species of hybrid origin is likely due to slowing of concerted evolution caused by the long generation time of peonies. The partial and uneven homogenization of parental sequences displayed in nine species of putative hybrid origin may have resulted from gradients of gene conversion. The documented hybridizations may have occurred since the Pleistocene glaciations. The species of hybrid origin and their putative parents are now distantly allopatric. Reconstruction of reticulate evolution with sequence data, therefore, provides gene records for distributional histories of some of the parental species. Images Fig. 1 PMID:7624325

  16. Steryl Glycoside Formation in Seedlings of Nicotiana tabacum L. 1

    PubMed Central

    Bush, Parshall B.; Grunwald, C.

    1974-01-01

    Particulate enzyme preparations from tobacco seedlings (Nicotiana tabacum L.) were used in the synthesis of steryl glycoside. The data obtained by measuring cholesterol-4-14C incorporation generally agree with results obtained with UDP-glucose-14C. The in vitro reaction was linear for the first 10 minutes and had a pH optimum of 7.0 to 7.4. Addition of ATP activated while UDP-glucose inhibited slightly the reaction. In short term experiments, the percentage disappearance of endogenous and added sterol was about the same. Intact tobacco seedlings incorporated cholesterol-4-14C and sitosterol-4-14C into their steryl glycosides. The acylated steryl glycosides were more rapidly labeled than the nonacylated form. After 12 hours of incubation with cholesterol-4-14C, about 5% of the radioactivity was recovered as steryl glycoside and 12% as acylated steryl glycoside. Incubation for 12 hours with authentic cholesteryl-14C glucoside gave only a 4% acylation, and under these conditions 21% of the radioactivity was recovered as free cholesterol. It is suggested that acylated steryl glycosides may be formed through the acylation of steryl glycosides or the transfer of an acyl-glycosyl group to sterol. PMID:16658662

  17. Steviol glycoside safety: are highly purified steviol glycoside sweeteners food allergens?

    TOXLINE Toxicology Bibliographic Information

    Urban JD; Carakostas MC; Taylor SL

    2015-01-01

    Steviol glycoside sweeteners are extracted from the plant Stevia rebaudiana (Bertoni), a member of the Asteraceae (Compositae) family. Many plants from this family can induce hypersensitivity reactions via multiple routes of exposure (e.g., ragweed, goldenrod, chrysanthemum, echinacea, chamomile, lettuce, sunflower and chicory). Based on this common taxonomy, some popular media reports and resources have issued food warnings alleging the potential for stevia allergy. To determine if such allergy warnings are warranted on stevia-based sweeteners, a comprehensive literature search was conducted to identify all available data related to allergic responses following the consumption of stevia extracts or highly purified steviol glycosides. Hypersensitivity reactions to stevia in any form are rare. The few cases documented in the peer-reviewed literature were reported prior to the introduction of high-purity products to the market in 2008 when many global regulatory authorities began to affirm the safety of steviol glycosides. Neither stevia manufacturers nor food allergy networks have reported significant numbers of any adverse events related to ingestion of stevia-based sweeteners, and there have been no reports of stevia-related allergy in the literature since 2008. Therefore, there is little substantiated scientific evidence to support warning statements to consumers about allergy to highly purified stevia extracts.

  18. Determination of phenylethanoid glycosides and iridoid glycosides from therapeutically used Plantago species by CE-MEKC.

    PubMed

    Gonda, Sndor; Nguyen, Nhat Minh; Batta, Gyula; Gymnt, Gyngyi; Mth, Csaba; Vasas, Gbor

    2013-09-01

    CE methods are valuable tools for medicinal plant quality management, screening, and analysis. Therefore, the aim of the current study was to optimize and validate a CE-MEKC method for simultaneous quantification of four chief bioactive metabolites from Plantago species. The two most important secondary metabolite groups were aimed to be separated. Different electrolyte and surfactant types were tested. Surfactant concentration, BGE pH, electrolyte concentration, and buffering capacity were optimized. The final BGE consisted of 15 mM sodium tetraborate, 20 mM TAPS, and 250 mM DOC at pH 8.50. Acceptable precision, good stability, and accuracy were achieved, with high resolution for phenylethanoid glycosides. Analytes were separated within 20 min. The method was shown to be suitable for the quantification of the iridoid glycosides aucubin and catalpol, and the phenylethanoid glycosides acteoside (verbascoside) and plantamajoside from water extracts of different samples. The method was shown to be applicable to leaf extracts of Plantago lanceolata, Plantago major, and Plantago asiatica, the main species with therapeutic applications, and a biotechnological product, plant tissue cultures (calli) of P. lanceolata. Baseline separation of the main constituents from minor peaks was achieved, regardless of the matrix type. PMID:23784714

  19. Steviol glycoside safety: are highly purified steviol glycoside sweeteners food allergens?

    PubMed

    Urban, Jonathan D; Carakostas, Michael C; Taylor, Steve L

    2015-01-01

    Steviol glycoside sweeteners are extracted from the plant Stevia rebaudiana (Bertoni), a member of the Asteraceae (Compositae) family. Many plants from this family can induce hypersensitivity reactions via multiple routes of exposure (e.g., ragweed, goldenrod, chrysanthemum, echinacea, chamomile, lettuce, sunflower and chicory). Based on this common taxonomy, some popular media reports and resources have issued food warnings alleging the potential for stevia allergy. To determine if such allergy warnings are warranted on stevia-based sweeteners, a comprehensive literature search was conducted to identify all available data related to allergic responses following the consumption of stevia extracts or highly purified steviol glycosides. Hypersensitivity reactions to stevia in any form are rare. The few cases documented in the peer-reviewed literature were reported prior to the introduction of high-purity products to the market in 2008 when many global regulatory authorities began to affirm the safety of steviol glycosides. Neither stevia manufacturers nor food allergy networks have reported significant numbers of any adverse events related to ingestion of stevia-based sweeteners, and there have been no reports of stevia-related allergy in the literature since 2008. Therefore, there is little substantiated scientific evidence to support warning statements to consumers about allergy to highly purified stevia extracts. PMID:25449199

  20. Biosynthesis of daunorubicin glycosides: role of epsilon-rhodomycinone.

    PubMed Central

    McGuire, J C; Thomas, M C; Stroshane, R M; Hamilton, B K; White, R J

    1980-01-01

    Daunorubicin (daunomycin; NSC 82151) is a fermentation-derived anthracycline antibiotic that is clinically useful in the treatment of human leukemias. Daunorubicin itself is found rarely in microbial fermentations, but is present normally in the form of glycoside derivatives that yield the free drug on simple acid hydrolysis. A major by-product of daunorubicin fermentations is usually the structurally related anthracyclinone epsilon-rhodomycinone. We have used mutants of a daunorubicin-producing Streptomyces species to study the biosynthetic relationship between epsilon-rhodomycinone and daunorubicin. We found that exogenously added epsilon-rhodomycinone can be converted to daunorubicin glycosides by a nonproducing mutant and by a mutant that produces daunorubicin glycosides but not epsilon-rhoeomycinone. Molar conversion efficiences were in the 15 to 30% range. The latter mutant was also shown to convert exogenous 14C-labeled epsilon-rhodomycinone to 14C-labeled daunorubicin glycosides, again at conversion efficiencies of about 25%. The same biotransformation was observed with daunorubicin production strain C5, which normally accumulates both epsilon-rhodomycinone and daunorubicin glycosides. A significant percentage (16 to 37%) of exogenously added epsilon-[14C]rhodomycinone was metabolized by strain C5, and 22 to 32% of the metabolized radioactivity could be recovered as daunorubicin glycosides. A mathematical model of epsilon-rhodomycinone metabolism was constructed based on plausible assumptions concerning the kinetics of epsilon-rhodomycinone accumulation and catabolsim. When analyzed according to this model, our data indicate that most (63 to 73%), but not all, of the daunorubicin glycosides accumulated in the experiments with production strain C5 derived from epsilon-rhodomycinone. A pathway network for the biosynthesis of daunorubicin glycosides is proposed that is in agreement with these data. In this proposed pathway network, epsilon-rhodomycinone is an intermediate in one of at least two pathways which yield daunorubicin glycosides. Images PMID:7425613

  1. Influence of derivation on the lipophilicity and inhibitory actions of cardiac glycosides on myocardial Na+-K+-ATPase.

    PubMed Central

    Dzimiri, N.; Fricke, U.; Klaus, W.

    1987-01-01

    Lipophilicity and inhibitory actions on guinea-pig heart Na+-K+-ATPase of twenty-six digitalis and six strophanthus glycosides comprising the aglycones, mono-, bis-, tris-sugar, alkylated (acylated) tris-sugar, acyl steroid derivatives and three cardanolides were investigated. Their octanol/water partition coefficients (P), reversed phase thin layer (r.t.l.c.) and reversed phase high performance liquid chromatography (r.h.p.l.c.) were determined and the viability of these methods as a measure of the lipophilicity of the cardiotonic steroids evaluated. The influence of lipophilicity and so also structural changes on the inhibitory effects of the cardiac glycosides on myocardial Na+-K+-ATPase was then examined. It is concluded that (a) r.t.l.c. and r.h.p.l.c. are just as effective as the conventional shake-flask method for estimation of the lipophilicity of cardiac glycosides and (b) the inhibitory potencies of cardiotonic steroids on the myocardial Na+-K+-ATPase increase with growing lipophilicity. The relationship between these two parameters is, however, governed by the influence of substitution or derivation of structural components on their inhibitory potencies on the myocardial Na+-K+-ATPase. PMID:3036289

  2. HPLC-PDA method for quinovic acid glycosides assay in Cat's claw (Uncaria tomentosa) associated with UPLC/Q-TOF-MS analysis.

    PubMed

    Pavei, Cabral; Kaiser, Samuel; Verza, Simone Gasparin; Borre, Gustavo Luis; Ortega, George Gonzalez

    2012-03-25

    Uncaria tomentosa (Willd.) is a medicinal plant largely used in folk medicine due to its wide range of biological activities, many of which are usually ascribed to the two main classes of secondary metabolites, namely, alkaloids and quinovic acid glycosides. In this work, a reversed phase HPLC-PDA method was developed and validated for the assay of quinovic acid glycosides in crude and dried extracts of Uncaria tomentosa (Cat's claw) bark. The validation comprised tests of specificity, accuracy, linearity, intermediate precision, repeatability and limits of detection and of quantification. Alpha-hederin was used as the external standard. High coefficients of determination with lower R.S.D. were achieved for both external standard and crude extract. The structural characterization of the main quinovic acid glycosides presented in the crude extract was carried out through UPLC/Q-TOF-MS. The identities of the compounds were obtained through the comparison of their fragmentation patterns with those reported in the literature. The analytical method was successfully applied for quantifying quinovic acid glycosides in two different dried extracts from U. tomentosa and in one quinovic acid glycosides purified fraction. PMID:22296654

  3. Cardiac glycosides and pregnanes from Adenium obesum (studies on the constituents of Adenium. I).

    PubMed

    Yamauchi, T; Abe, F

    1990-03-01

    Cardiac glycosides and pregnanes from the roots and the stems of Adenium obesum Roem. et Schult. were investigated. Among 30 cardiac glycosides including 15 known glycosides and 15 new combinations of the known aglycones and sugars, the structures of 11 glycosides were elucidated. Oleandrigenin beta-gentiobiosyl-beta-D-thevetoside was the main glycoside. Neridienone A and 16,17-dihydroneridienone A, common pregnanes in Apocynaceae, were also isolated. PMID:2347008

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

    PubMed

    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 ?M, while two others inhibited both inflammatory mediators with IC50 values of 0.66-3.49 ?M. Structure-activity relationships are discussed. PMID:23838628

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

    PubMed

    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. PMID:22717506

  6. Use of cardiac glycosides and risk of glioma.

    PubMed

    Seliger, Corinna; Meier, Christoph R; Jick, Susan S; Uhl, Martin; Bogdahn, Ulrich; Hau, Peter; Leitzmann, M F

    2016-04-01

    Cardiac glycosides induce apoptotic effects on glioma cells, but whether cardiac glycosides protect against risk for glioma is unknown. We therefore explored the relation between glycoside use and glioma risk using a large and validated database. We performed a case-control analysis using the Clinical Practice Research Datalink involving 2005 glioma cases diagnosed between 1995 and 2012 that were individually matched to 20,050 controls on age, gender, general practice, and number of years of active history in the database. Conditional logistic regression analysis was used to evaluate the association between cardiac glycosides and the risk of glioma adjusting for body mass index and smoking. We also examined use of common heart failure and arrhythmia medications to differentiate between a specific glycoside effect and a generic effect of treatment for congestive heart failure or arrhythmia. Cardiac glycoside use was inversely related to glioma incidence. After adjustment for congestive heart failure, arrhythmia, diabetes, and common medications used to treat those conditions, the OR of glioma was 0.47 (95 % CI 0.27-0.81, Bonferroni-corrected p value = 0.024) for use versus non-use of cardiac glycosides, based on 17 exposed cases. In contrast, no associations were noted for other medications used to treat congestive heart failure or arrhythmias. The OR of glioma in people with congestive heart failure was 0.65 (95 % CI 0.40-1.04), and for arrhythmia it was 1.01 (95 % CI 0.78-1.31). These data indicate that cardiac glycoside use is independently associated with reduced glioma risk. PMID:26721242

  7. Unusual Flavonoid Glycosides from the Hawaiian Tree Metrosideros polymorpha.

    PubMed

    Clark, Benjamin R; Pramanick, Swapan; Arancon, Norman; Borris, Robert P

    2015-06-01

    Metrosideros polymorpha is a highly variable and widely-distributed tree native to the Hawaiian islands. We describe here the isolation of two new gossypetin derivatives and three new C-methylated flavonol glycosides, which are highly uncommon and may prove to be useful chemotaxonomic markers for the species. In addition, a wide range of known flavonoid glycosides, chalcones, and terpenoids were isolated alongside the new compounds. PMID:26197518

  8. Diterpenoid glycosides from the bitter fern Gleichenia quadripartita.

    PubMed

    Socolsky, Cecilia; Asakawa, Yoshinori; Bardn, Alicia

    2007-12-01

    Fifteen new diterpenoid glycosides (1a-n, 2) were isolated from an Argentine collection of the bitter fern Gleichenia quadripartita along with the known flavonoid glycoside afzelin. Structure elucidation was accomplished by 1D and 2D NMR spectroscopy and by high-resolution MS analyses. In addition, X-ray crystallographic analysis of a monocrystal of 1a as well as chemical derivatization of 1h and 1m were performed to confirm their structures. PMID:18161941

  9. A new acylated flavonol glycoside from Derris triofoliata.

    PubMed

    Xu, Lu-Rong; Wu, Jun; Zhang, Si

    2006-01-01

    A new acylated flavonol glycoside, kaempferol 3-O-[(6''''-feruloyl)-beta-D-glucopyranosyl-(1 --> 3)]-[alpha-L-rhamnopyranosyl-(1 --> 6)]-beta-D-glucopyranoside and two known cyclolignan glycosides, (+)-lyoniresinol-3alpha-O-beta-D-glucopyranoside and ( - )-lyoniresinol-3alpha-O-beta-D-glucopyranoside were isolated from n-BuOH extracts of the aerial parts of Derris triofoliata, their structures were determined from spectroscopic and chemical evidences. PMID:16753776

  10. Secoiridoid glycoside and alkaloid constituents of Hydrangea chinensis.

    PubMed

    Chang, Fang-Rong; Lee, Yue-Han; Yang, Yu-Liang; Hsieh, Pei-Wen; Khalil, Ashraf T; Chen, Chung-Yi; Wu, Yang-Chang

    2003-09-01

    A new secoiridoid glycoside, hydrachoside A (1), along with 14 known compounds, was isolated from the leaves of Hydrangea chinensis. The absolute stereochemistry of the side chain attached to C-15 on the secoiridoid glycoside hydrangenoside E (2) was determined by NMR spectral analysis. The structures of compounds 1 and 2 were elucidated on the basis of spectral data. The previously reported structure, hydrachine A (3), was revised as its epimer, (-)-neodichroine (4), a new compound. PMID:14510608

  11. Genetic Structure of the Tree Peony (Paeonia rockii) and the Qinling Mountains as a Geographic Barrier Driving the Fragmentation of a Large Population

    PubMed Central

    Yuan, Junhui; Cheng, FangYun; Zhou, ShiLiang

    2012-01-01

    Background Tree peonies are great ornamental plants associated with a rich ethnobotanical history in Chinese culture and have recently been used as an evolutionary model. The Qinling Mountains represent a significant geographic barrier in Asia, dividing mainland China into northern (temperate) and southern (semitropical) regions; however, their flora has not been well analyzed. In this study, the genetic differentiation and genetic structure of Paeonia rockii and the role of the Qinling Mountains as a barrier that has driven intraspecific fragmentation were evaluated using 14 microsatellite markers. Methodology/Principal Findings Twenty wild populations were sampled from the distributional range of P. rockii. Significant population differentiation was suggested (FST value of 0.302). Moderate genetic diversity at the population level (HS of 0.516) and high population diversity at the species level (HT of 0.749) were detected. Significant excess homozygosity (FIS of 0.076) and recent population bottlenecks were detected in three populations. Bayesian clusters, population genetic trees and principal coordinate analysis all classified the P. rockii populations into three genetic groups and one admixed Wenxian population. An isolation-by-distance model for P. rockii was suggested by Mantel tests (r?=?0.6074, P<0.001) and supported by AMOVA (P<0.001), revealing a significant molecular variance among the groups (11.32%) and their populations (21.22%). These data support the five geographic boundaries surrounding the Qinling Mountains and adjacent areas that were detected with Monmonier's maximum-difference algorithm. Conclusions/Significance Our data suggest that the current genetic structure of P. rockii has resulted from the fragmentation of a formerly continuously distributed large population following the restriction of gene flow between populations of this species by the Qinling Mountains. This study provides a fundamental genetic profile for the conservation and responsible exploitation of the extant germplasm of this species and for improving the genetic basis for breeding its cultivars. PMID:22523566

  12. DNA-N-glycosylases process novel O-glycosidic sites in DNA.

    PubMed

    Admiraal, Suzanne J; O'Brien, Patrick J

    2013-06-11

    After the hydrolysis of the N-glycosyl bond between a damaged base and C1' of a deoxyribosyl moiety of DNA, human alkyladenine DNA glycosylase (AAG) and Escherichia coli 3-methyladenine DNA glycosylase II (AlkA) bind tightly to their abasic DNA products, potentially protecting these reactive species. Here we show that both AAG and AlkA catalyze reactions between bound abasic DNA and small, primary alcohols to form novel DNA-O-glycosides. The synthesis reactions are reversible, as the DNA-O-glycosides are converted back into abasic DNA upon being incubated with AAG or AlkA in the absence of alcohol. AAG and AlkA are therefore able to hydrolyze O-glycosidic bonds in addition to N-glycosyl bonds. The newly discovered DNA-O-glycosidase activities of both enzymes compare favorably with their known DNA-N-glycosylase activities: AAG removes both methanol and 1,N(6)-ethenoadenine (?A) from DNA with single-turnover rate constants that are 2.9 10(5)-fold greater than the corresponding uncatalyzed rates, whereas the rate enhancement of 3.7 10(7) for removal of methanol from DNA by AlkA is 300-fold greater than its rate enhancement for removal of ?A from DNA. Although the biological significance of the DNA-O-glycosidase reactions is not known, the evolution of new DNA repair pathways may be aided by enzymes that practice catalytic promiscuity, such as these two unrelated DNA glycosylases. PMID:23688261

  13. Acylated Steryl Glycoside Synthesis in Seedlings of Nicotiana tabacum L. 1

    PubMed Central

    Frasch, Wayne; Grunwald, Claus

    1976-01-01

    In tobacco seedlings (Nicotiana tabacum L.), glucose from supplied uridine diphosphate-[U-14C]glucose was first incorporated into steryl glycosides and later into acylated steryl glycosides. However, when [14C]cholesterol was used as substrate, the acylated steryl glycosides became labeled earlier than the steryl glycosides. With [14C]cholesteryl glucoside as substrate, most of the radioactive label was recovered as free sterol, and the acylated steryl glycosides were not readily labeled; however, palmitoyl [14C]cholesteryl glucoside was rapidly converted to steryl glycoside. In feeding experiments with free sterol, an unknown, highly radioactive steroid component was isolated. Incorporation of radioactivity into the unknown occurred before the acylated steryl glycosides were labeled. It is postulated that two pathways exist for the biosynthesis of acylated steryl glycoside: one through steryl glycosides, and the other through an unidentified steroid component. It is the latter pathway which appears to be dominant in the in vivo tobacco system. PMID:16659758

  14. Studies on the localization of the cardiac glycoside receptor

    PubMed Central

    Smith, Thomas W.; Wagner, Henry; Markis, John E.; Young, Michael

    1972-01-01

    The purpose of this study was to see whether the receptor for cardiac glycosides might be localized upon or within the plasma membrane of digitalis-sensitive cells. Ouabain and digoxin were joined covalently to several large protein molecules. These macromolecular conjugates are too large to enter intact cells; consequently, any pharmacologic or biochemical effects which they display should arise from interaction with a cell surface receptor. Conjugates were tested in several cardiac glycoside-sensitive systems: (a), contractility response of isolated cardiac muscle; (b), active 86Rb+ uptake by red cells; (c), enzymatic activity of isolated myocardial microsomal (Na+ + K+)-activated adenosine triphosphatase (ATPase); and (d), enzymatic activity of solubilized red cell (Na+ + K+)-activated ATPase. Results demonstrated that in all of these systems, the macromolecular-glycoside conjugates were 100- to 1000-fold less active than the free glycosides. Careful chromatographic examination of the various conjugates revealed that they contained a small but persistent free cardiac glycoside contaminant. The amount of this species ranged from 0.1 to 1.0% of the total macromolecule-bound glycoside, and its presence fully explains the levels of biologic activity observed with the conjugates. To try to minimize steric factors which could interfere with glycoside-receptor interaction, digoxin and ouabain were also coupled to macromolecule via long, flexible polyamide side-chains. These extended chain conjugates, in which the cardiac glycoside potentially lay some 30 A removed from the surface of the macromolecule, also exhibited negligible digitalis-like effects when tested upon isolated cardiac muscle, red cell 86Rb+ uptake, and enzymatic activity of cardiac microsomal (Na+ + K+)-ATPase. However, the extended chain conjugates were fully active when examined with the solubilized red cell (Na+ + K+)-ATPase system. To further ensure that the chemical reactions used to couple macromolecule to glycoside did not inactivate the drug, all conjugates were subjected to extensive proteolytic digests exhibited full pharmacologic activity. Digoxin was also coupled to the tripeptide alanylglycylglycine, and the resulting conjugate was fully active. Taken together, these results suggest that if the receptor(s) for cardiac glycosides is associated with the plasma membrane, then it may lie deep within it. Images PMID:4260687

  15. Cytotoxic Flavonoid Glycosides from Rapistrum rugosum L.

    PubMed Central

    Mohamed Al-Taweel, Areej; Ahmed Fawzy, Ghada; Perveen, Shagufta

    2012-01-01

    Five flavonoid glycosides were isolated from the n-butanol soluble fraction of the ethanolic extract of Rapistrum rugosum and their structures were assigned from 1H- and 13C-NMR spectra (DEPT) with 2D NMR as quercetin-3-O-?-L-rhamnopyranoside (1), quercetin-3-O- ?-D-xyloside (2), quercetin, 3-O-?-L-arabinopyranoside,7-O-?-L-rhamnopyranoside (3), kaempferol 3-O-?-L-arabinopyranoside, 7-O-?-L-rhamnopyranoside (4) and rutin (5). The SRB cytotoxic assay was used to investigate the antitumor activities of n-butanol extract, compound 3 and its hexaacetate 3a, for the first time. Compounds 3 and 3a showed cytotoxic activity against the human cancer cell line, namely, HepG2 (hepatocellular carcinoma cell line) with IC50 (concentration of compound required to reduce cell survival by 50%) 0.86 ?g/mL and 3.50 ?g/mL, respectively. These results proved that compound 3, the major flavonoid of the n-butanol soluble fraction, has significant cytotoxic activity compared with the standard antitumor drug doxorubicin (0.60 ?g/mL). PMID:24250510

  16. Pharmacological treatment of cardiac glycoside poisoning.

    PubMed

    Roberts, Darren M; Gallapatthy, Gamini; Dunuwille, Asunga; Chan, Betty S

    2016-03-01

    Cardiac glycosides are an important cause of poisoning, reflecting their widespread clinical usage and presence in natural sources. Poisoning can manifest as varying degrees of toxicity. Predominant clinical features include gastrointestinal signs, bradycardia and heart block. Death occurs from ventricular fibrillation or tachycardia. A wide range of treatments have been used, the more common including activated charcoal, atropine, ?-adrenoceptor agonists, temporary pacing, anti-digoxin Fab and magnesium, and more novel agents include fructose-1,6-diphosphate (clinical trial in progress) and anticalin. However, even in the case of those treatments that have been in use for decades, there is debate regarding their efficacy, the indications and dosage that optimizes outcomes. This contributes to variability in use across the world. Another factor influencing usage is access. Barriers to access include the requirement for transfer to a specialized centre (for example, to receive temporary pacing) or financial resources (for example, anti-digoxin Fab in resource poor countries). Recent data suggest that existing methods for calculating the dose of anti-digoxin Fab in digoxin poisoning overstate the dose required, and that its efficacy may be minimal in patients with chronic digoxin poisoning. Cheaper and effective medicines are required, in particular for the treatment of yellow oleander poisoning which is problematic in resource poor countries. PMID:26505271

  17. Resin Glycosides from the Morning Glory Family

    NASA Astrophysics Data System (ADS)

    Pereda-Miranda, Rogelio; Rosas-Ramrez, Daniel; Castaeda-Gmez, Jhon

    Resin glycosides are part of a very extensive family of secondary metabolites known as glycolipids or lipo-oligosaccharides and are constituents of complex resins (glycoresins) (1) unique to the morning glory family, Convolvulaceae (2). These active principles are responsible for the drastic purgative action of all the important Convolvulaceous species used in traditional medicine throughout the world since ancient times. Several commercial purgative crude drugs can be prepared from the roots of different species of Mexican morning glories. Their incorporation as therapeutic agents in Europe is an outstanding example of the assimilation of botanical drugs from the Americas as substitutes for traditional Old World remedies (3). Even though phytochemical investigations on the constituents of these drugs were initiated during the second half of the nineteenth century, the structure of their active ingredients still remains poorly known for some examples of these purgative roots. During the last two decades, the higher resolution capabilities of modern analytical isolation techniques used in conjunction with powerful spectroscopic methods have facilitated the elucidation of the active principles of these relevant herbal products.

  18. 30-normedicagenic acid glycosides from Chenopodium foliosum.

    PubMed

    Nedialkov, Paraskev T; Kokanova-Nedialkova, Zlatina; Bcherl, Daniel; Momekov, Georgi; Heilmann, Jrg; Nikolov, Stefan

    2012-11-01

    Two new glycosides of 30-normedicagenic acid, namely 3-O-[beta-D-glucuronopyranosyl methyl ester]-2beta,3beta-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28-O-beta-D-glucopyranosyl ester, and 3-O-beta-D-glucopyranosyl-2beta,3beta-dihydroxy-30-noroleane- 12,20(29)-diene-23,28-dioic acid, together with the known 3-O-beta-glucopyranosyl-2beta,3beta-dihydroxy-30-noroleane-12,20(29)-diene-23 ,28-dioic acid 28-O-beta-glucopyranosyl ester, and 3-O-beta-glucuronopyranosyl-2beta,3beta-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28-O-beta-glucopyranosyl ester were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR) and HRMS-ESI. The compounds were tested for cytotoxicity on three leukemic cell lines (BV-173, SKW-3, HL-60). In addition, the saponins showed moderate stimulatory effects on interleukin-2 production in PHA/PMA stimulated Jurkat E6.1 cells. PMID:23285798

  19. An Optimized Combination of Ginger and Peony Root Effectively Inhibits Amyloid-β Accumulation and Amyloid-β-Mediated Pathology in AβPP/PS1 Double-Transgenic Mice.

    PubMed

    Lim, Soonmin; Choi, Jin Gyu; Moon, Minho; Kim, Hyo Geun; Lee, Wonil; Bak, Hyoung-Rok; Sung, Hachang; Park, Chi Hye; Kim, Sun Yeou; Oh, Myung Sook

    2015-11-30

    The progressive aggregation of amyloid-β protein (Aβ) into senile plaques is a major pathological factor of Alzheimer's disease (AD) and is believed to result in memory impairment. We aimed to investigate the effect of an optimized combination of ginger and peony root (OCGP), a standardized herbal mixture of ginger and peony root, on Aβ accumulation and memory impairment in amyloid-β protein precursor (AβPP)/presenilin 1 (PS1) double-transgenic mice. In an in vitro thioflavin T fluorescence assay, 100 μg/ml OCGP inhibited Aβ accumulation to the same extent as did 10 μM curcumin. Furthermore, AβPP/PS1 double-transgenic mice treated with OCGP (50 or 100 mg/kg/day given orally for 14 weeks) exhibited reduced Aβ plaque accumulation in the hippocampus and lower levels of glial fibrillary acid protein and cyclooxygease-2 expression compared with vehicle-treated controls. These results suggest that OCGP may prevent memory impairment in AD by inhibiting Aβ accumulation and inflammation in the brain. PMID:26639976

  20. Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis.

    PubMed

    Zhang, Jie; Koike, Ryosuke; Yamamoto, Ayako; Ukiya, Motohiko; Fukatsu, Makoto; Banno, Norihiro; Miura, Motofumi; Motohashi, Shigeyasu; Tokuda, Harukuni; Akihisa, Toshihiro

    2013-10-01

    A new flavonoid glycoside, chrysin 6-C-?-rutinoside (chrysin ?-L-rhamnopyranosyl-(1?6)-C-?-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with ?-melanocyte-stimulating hormone (?-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.3-47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8-100.2% cell viability) at 100??M. Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP-1, and tyrosinase, in a concentration-dependent manner while exerted almost no influence on the level of TRP-2, suggesting that this compound inhibits melanogenesis on the ?-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP-1 and tyrosinase. In addition, compounds 1-17 were evaluated for their inhibitory effects against the Epstein?Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. PMID:24130028

  1. Structures of some novel ?-glucosyl diterpene glycosides from the glycosylation of steviol glycosides.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2014-01-01

    Four new minor diterpene glycosides with a rare ?-glucosyl linkage were isolated from a cyclodextrin glycosyltransferase glucosylated stevia extract containing more than 98% steviol glycosides. The new compounds were identified as 13-[(2-O-?-D-glucopyranosyl-3-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-?-D-glucopyranosyl-?-D-glucopyranosyl) ester] (1), 13-[(2-O-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-(4-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl ester] (2), 13-[(2-O-?-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid ?-D-glucopyranosyl ester (3), and 13-[(2-O-?-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl- ?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-?-D-glucopyranosyl-?-D-glucopyranosyl) ester] (4) on the basis of extensive NMR and mass spectral (MS) data as well as hydrolysis studies. PMID:25486243

  2. Pregnane steroidal glycosides and their cytostatic activities.

    PubMed

    Garca, Vctor P; Bermejo, Jaime; Rubio, Sara; Quintana, Jos; Estvez, Francisco

    2011-05-01

    Four new steroidal glycosides such as 3-O-6-deoxy-3-O-methyl-?-D-allopyranosyl-(1 ? 4)-?-D-oleandropyranosyl-(1 ? 4)-?-D-cymaropyranosyl-(1 ? 4)-?-D-cymaropyranoside-12-?-tigloyl-14-?-hydroxy-17-?-pregnane (1), 3-O-6-deoxy-3-O-methyl-?-D-allopyranosyl-(1 ? 4)-?-D-oleandropyranosyl-(1 ? 4)-?-D-cymaropyranosyl-(1 ? 4)-?-D-cymaropyranoside-12-?-(2'-amino)-benzoyl-14-?-hydroxy-17-?-pregnane (2), 3-O-6-deoxy-3-O-methyl-?-D-allopyranosyl-(1 ? 4)-?-D-oleandropyranosyl-(1 ? 4)-?-D-cymaropyranosyl-(1 ? 4)-?-D-cymaropyranoside-12-?-14-?-dihydroxy-17-?-pregnane (3) and 3-O-6-deoxy-3-O-methyl-?-D-allopyranosyl-(1 ? 4)-?-D-oleandropyranosyl-(1 ? 4)-?-D-cymaropyranosyl-(1 ? 4)-?-D-cymaropyranoside-12-?-14-?-dihydroxy-17-?-pregnane (4) were isolated from the aerial parts of Ceropegia fusca Bolle (Asclepiadaceae), a crassulacean acid metabolism plant, an endemic species to the Canary Islands that has been used in traditional medicine as a cicatrizant, vulnerary and disinfectant. The dichloromethane extract exhibited significant cytostatic activity against HL-60, A-431 and SK-MEL-1 cells, human leukemic, epidermoid carcinoma and melanoma cells, respectively. As shown in Table I, compounds 1 and 2 showed very similar IC(50) values. The acetylation of 1 to give the diacetate 5 increases 5-fold the cytotoxicity against HL-60 cells. Compounds 3 and 4 did not show cytotoxicity at the assayed concentrations. With respect to the compounds containing only the steroid ring (6-8), the presence of a charged O-amino-benzoyl but not a tigloyl group improved the cytotoxicity. PMID:21147757

  3. ISOFLAVONE CONJUGATES AND MINOR GLYCOSIDES EXTRACTED FROM PEANUT HEARTS USING HPLC-MS

    Technology Transfer Automated Retrieval System (TEKTRAN)

    High performance liquid chromatography and electrospray mass spectrometry (ESI) was used to characterize isoflavone glycosidic conjugates and minor glycosides extracted from peanut meal. The selected extraction method combined the removal of isoflavones and their conjugates with an alcoholic solvent...

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  5. Complexation of alkyl glycosides with α-cyclodextrin can have drastically different effects on their conversion by glycoside hydrolases.

    PubMed

    Rather, Mohd Younis; Nordberg Karlsson, Eva; Adlercreutz, Patrick

    2015-04-20

    Substrates present in aggregated forms, such as micelles, are often poorly converted by enzymes. Alkyl glycosides constitute typical examples and the critical micelle concentration (CMC) decreases with increasing length of the alkyl group. In this study, possibilities to hydrolyse alkyl glycosides by glycoside hydrolases were explored, and α-cyclodextrin was used as an agent to form inclusion complexes with the alkyl glycosides, thereby preventing micelle formation. The cyclodextrin complexes were accepted as substrates by the enzymes to variable extent. The β-glucosidases originating from Thermotoga neapolitana (Tn Bgl3B) and from almond were not at all able to hydrolyse alkyl β-glucosides in the presence of 100mM α-cyclodextrin. However, Aspergillus niger amyloglucosidase readily accepted the complexes as substrates. In reactions involving decyl and dodecyl maltosides, the presence of 100mM α-cyclodextrin caused an increase in reaction rate in most cases, especially at high substrate concentrations. Surprisingly, the amyloglucosidase-catalyzed hydrolysis of octyl-β-maltoside to glucose and β-octylglucoside was faster in the presence of α-cyclodextrin than without, even at substrate concentrations below CMC. A possible explanation of the observed rate enhancement is that binding sites on the carbohydrate binding domain of amyloglucosidase, known to bind cyclodextrins, help to guide the alkyl glycoside-cyclodextrin complex to the active site, and thereby promote its conversion. PMID:25711178

  6. 2-methyl-L-erythritol glycosides from Gardenia jasminoides.

    PubMed

    Yang, Liguo; Peng, Kaifeng; Zhao, Shizhe; Zhao, Feng; Chen, Lixia; Qiu, Feng

    2013-09-01

    Two new glycosides, 2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-?-D-glucopyranoside (1) and 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-?-D-glucopyranoside (2), along with two known triterpenoids (3-4), four quinic acid derivatives (5-8) and one flavonoid (9) were isolated from the fruit of Gardenia jasminoides. Their structures were elucidated through MS and 2D NMR experiments (HMQC and HMBC). Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. Though 2-methyl-D-erythritol and its glycosides have been reported in a few references, this is the first report about 2-methyl-L-erythritol glycosides. Based on this finding, we propose that 2-methyl-L-erythritol might be a new intermediate in the non-mevalonate biosynthesis of terpenoids. PMID:23727470

  7. Synthesis and photosensitivity of isoxazolin-5-one glycosides.

    PubMed

    Becker, Tobias; Kartikeya, Prashant; Paetz, Christian; von Reuss, Stephan H; Boland, Wilhelm

    2015-04-01

    A novel procedure for the synthesis of isoxazolin-5-one glycosides starting from unprotected carbohydrates is described. The substrate scope of the one-pot synthetic protocol was explored using D-configured glucose, xylose, maltose, fructose, ribose and 2-deoxyribose. Naturally occurring 2-(?-D-glucopyranosyl)-3-isoxazolin-5-one and four novel isoxazolin-5-one glycosides derived from xylose, maltose and fructose were synthesized and purified by flash chromatography. The compounds were characterized in terms of chemical structure, photophysical properties as well as pH stability. The photohydrolysis rates of the synthesized glycosides were compared with uridine as a standard to determine the quantum yields for the photoreactions in water. PMID:25723136

  8. Cardiac Glycosides from the Seeds of Thevetia peruviana.

    PubMed

    Tian, Dan-Mei; Cheng, Huo-Yun; Jiang, Miao-Miao; Shen, Wei-Zai; Tang, Jin-Shan; Yao, Xin-Sheng

    2016-01-22

    Investigation of the seeds of Thevetia peruviana resulted in the isolation of 15 new (2-16) and 18 known (1 and 17-33) cardiac glycosides. Eight 19-nor-cardenolides (1-8), including two rare 19-nor-10-hydroperoxycardenolides, were obtained from T. peruviana for the first time. All the structures were characterized by NMR spectroscopy and chemical derivatization. The inhibitory effects of cardiac glycosides 1-33 against three cancer cell lines (human lung cancer cells, P15; human gastric cancer cells, MGC-803; and human pancreatic cancer cells, SW1990) and one normal hepatocyte cell line, LO2, were evaluated, and a preliminary structure-activity relationship is discussed. In addition, cardiac glycosides 1, 22, 26, and 28 were evaluated for their apoptosis-inducing activities in MGC-803 cells, showing IC50 values in the range 0.02-0.53 ?M. PMID:26714048

  9. Sesquiterpene glycosides from the roots of Codonopsis pilosula

    PubMed Central

    Jiang, Yueping; Liu, Yufeng; Guo, Qinglan; Xu, Chengbo; Zhu, Chenggen; Shi, Jiangong

    2015-01-01

    Three new sesquiterpene glycosides, named codonopsesquilosides A−C (1−3), were isolated from an aqueous extract of the dried roots of Codonopsis pilosula. Their structures including absolute configurations were determined by spectroscopic and chemical methods. These glycosides are categorized as C15 carotenoid (1), gymnomitrane (2), and eudesmane (3) types of sesquiterpenoids, respectively. Compound 1 is the first diglycoside of C15 carotenoids to be reported. Compound 2 represents the second reported example of gymnomitrane-type sesquiterpenoids from higher plants. The absolute configurations were supported by comparison of the experimental circular dichroism (CD) spectra with the calculated electronic CD (ECD) spectra of 1−3, their aglycones, and model compounds based on quantum-mechanical time-dependent density functional theory. The influences of the glycosyls on the calculated ECD spectra of the glycosidic sesquiterpenoids, as well as some nomenclature and descriptive problems with gymnomitrane-type sesquiterpenoids are discussed. PMID:26904398

  10. New flavonol glycosides from leaves of Symplocarpus renifolius.

    PubMed

    Whang, W K; Lee, M T

    1999-08-01

    A study was carried out to evaluate flavonol glycosides in leaves of Symplocarpus renifolius (Araceae). From the water fraction of the MeOH extract, three new flavonol glycosides were isolated along with three known compounds, kaempferol-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-7-O-b eta-D-glucopyranoside,quercetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D -glucopyranoside, and caffeic acid. The structures of the new flavonol glycosides were elucidated by chemical and spectral analyses as quercetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-7-O-be ta-D-glucopyranoside, isorhamnetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyra nos yl-7-O-beta-D-glucopyranoside, and quercetin-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-7-O-(6 ''''-trans-caffeoyl)-beta-D-glucopyranoside. PMID:10489886

  11. Steroidal sapogenins and glycosides from the rhizomes of Dioscorea bulbifera.

    PubMed

    Liu, Hai; Chou, Gui-Xin; Wu, Tao; Guo, Yin-Long; Wang, Shun-Chun; Wang, Chang-Hong; Wang, Zheng-Tao

    2009-11-01

    Four new steroidal sapogenins (1-4), named diosbulbisins A-D, two new spirostane glycosides, diosbulbisides A (5) and B (6), one new cholestane glycoside, diosbulbiside C (7), and the known compounds 8-10 were isolated from rhizomes of Dioscorea bulbifera. Their structures were elucidated by 1D and 2D NMR techniques, HRFTMS, and chemical methods. The unusual furospirostanol sapogenin skeletons, as found in compounds 3 and 4, are reported in the family Dioscoreaceae for the first time. Cytotoxicity of compounds 1-10 was evaluated using two human hepatocellular carcinoma cell lines (Bel-7402 and SMMC7721). PMID:19842682

  12. One new cycloartane triterpene glycoside from Beesia calthaefolia.

    PubMed

    Zhao, Jin-Yuan; Mu, Li-Hua; Dong, Xian-Zhe; Hu, Yuan; Liu, Ping

    2016-02-01

    One new cycloartane triterpene glycoside (1) was isolated from the whole plant of Beesia calthaefolia. Its structure was elucidated on the basis of extensive spectroscopic data analysis. Its inhibitory effect was measured by the classical pathway of the complement system, and compared with those of known related cycloartane glycosides 2 and 3, previously isolated by us from the same plant. Compounds 1 and 2 exhibited inhibitory activity of complement system with IC50 of 395.3 and 214?M, respectively. The results suggested that OH at C-12, C-18 and C-15 along with the polarity could affect the inhibitory activity. PMID:26305784

  13. Flavonol Glycosides from the Leaves of Allium macrostemon.

    PubMed

    Nakane, Risa; Iwashina, Tsukasa

    2015-08-01

    Twelve flavonoids were isolated from Allium macrostemon leaves. Five compounds were identified as kaempferol 3,7-di-O-glucoside (1), kaempferol 3,4'-di-O-glucoside (2), quercetin 3-O-glucoside (3), kaempferol 3-0-glucoside (4) and isorhamnetin 3-O-glucoside (5) by UV spectra, LC-MS, acid hydrolysis and HPLC comparisons with authentic standards. Other flavonoids were characterized as kaempferol glycosides (6-8, 10 and 11) and quercetin glycosides (9 and 12). Other compounds, such as steroidal saponins, have been already found from the bulbs of A. macrostemon. However, flavonoids were reported for the first time from the leaves. PMID:26434122

  14. Two new abietane diterpenoid glycosides from Clinopodium chinense.

    PubMed

    Zhu, Yin-Di; Zhang, Jing-Yi; Li, Peng-Fei; Wu, Hai-Feng; Zhu, Nai-Liang; Jiang, Hai; Lv, Cui-Yan; Wu, Li-Li; Ma, Ze-Xin; Xu, Xu-Dong; Ma, Guo-Xu; Yang, Jun-Shan

    2016-05-01

    Two new abietane diterpenoid glycosides, named clinopoditerpenes B (1) and C (2), were isolated from Clinopodium chinese. The structures of the new compounds were determined on the basis of extensive spectral analysis. Compound 1 exhibited cardioprotective effect against H2O2-induced apoptosis in H9c2 cells. PMID:26551245

  15. Melanogenesis inhibitory activity of monoterpene glycosides from Gardeniae Fructus.

    PubMed

    Akihisa, Toshihiro; Watanabe, Kensuke; Yamamoto, Ayako; Zhang, Jie; Matsumoto, Masahiro; Fukatsu, Makoto

    2012-08-01

    A new iridoid glycoside, 10-O-(4"-O-methylsuccinoyl)geniposide (7), and two new pyronane glycosides, jasminosides Q and R (13 and 14, resp.), along with nine known iridoid glycosides, 1-6 and 8-10, and two known pyronane glycosides, 11 and 12, were isolated from a MeOH extract of Gardeniae Fructus, the dried ripe fruit of Gardenia jasminoides (Rubiaceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of compounds 1-14 on the melanogenesis in B16 melanoma cells induced with ?-melanocyte-stimulating hormone (?-MSH), three compounds, i.e., 6-O-p-coumaroylgeniposide (3), 7, and 6'-O-sinapoyljasminoside (12), exhibited inhibitory effects with 21.6-41.0 and 37.5-47.7% reduction of melanin content at 30 and 50 ?M, respectively, with almost no toxicity to the cells (83.7-106.1% of cell viability at 50 ?M). PMID:22899609

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

    ERIC Educational Resources Information Center

    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

  17. Triterpenoid glycosides from the leaves of Meliosma henryi.

    PubMed

    Alabdul Magid, Abdulmagid; Morjani, Hamid; Harakat, Dominique; Madoulet, Claudie; Dumontet, Vincent; Lavaud, Catherine

    2015-01-01

    Seven triterpenoid glycosides, named meliosmosides A-G, were isolated from the leaves of Meliosma henryi Diels (Sabiaceae). Their structures were elucidated by different spectroscopic methods including 1D and 2D NMR experiments as well as HRESIMS analysis. Isolated compounds were evaluated for their cytotoxic activity against KB cell line. PMID:25468712

  18. A new isoflavone glycoside from Ceiba pentandra (L.) Gaertner.

    PubMed

    Ueda, Hidenori; Kaneda, Norito; Kawanishi, Kazuko; Alves, Sergio Mello; Moriyasu, Masataka

    2002-03-01

    From the 80% EtOH extract of the bark of Ceiba pentandra (L.) Gaertner, a new isoflavone glycoside was isolated along with known isoflavones, vavain and vavain glucoside. The structure was elucidated by spectroscopic analysis as 5-hydroxy-7,4',5'-trimethoxyisoflavone 3'-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside. PMID:11911207

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

    ERIC Educational Resources Information Center

    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…

  20. Curation of characterized glycoside hydrolases of Fungal origin

    PubMed Central

    Murphy, Caitlin; Powlowski, Justin; Wu, Min; Butler, Greg; Tsang, Adrian

    2011-01-01

    Fungi produce a wide range of extracellular enzymes to break down plant cell walls, which are composed mainly of cellulose, lignin and hemicellulose. Among them are the glycoside hydrolases (GH), the largest and most diverse family of enzymes active on these substrates. To facilitate research and development of enzymes for the conversion of cell-wall polysaccharides into fermentable sugars, we have manually curated a comprehensive set of characterized fungal glycoside hydrolases. Characterized glycoside hydrolases were retrieved from protein and enzyme databases, as well as literature repositories. A total of 453 characterized glycoside hydrolases have been cataloged. They come from 131 different fungal species, most of which belong to the phylum Ascomycota. These enzymes represent 46 different GH activities and cover 44 of the 115 CAZy GH families. In addition to enzyme source and enzyme family, available biochemical properties such as temperature and pH optima, specific activity, kinetic parameters and substrate specificities were recorded. To simplify comparative studies, enzyme and species abbreviations have been standardized, Gene Ontology terms assigned and reference to supporting evidence provided. The annotated genes have been organized in a searchable, online database called mycoCLAP (Characterized Lignocellulose-Active Proteins of fungal origin). It is anticipated that this manually curated collection of biochemically characterized fungal proteins will be used to enhance functional annotation of novel GH genes. Database URL: http://mycoCLAP.fungalgenomics.ca/ PMID:21622642

  1. Reversible dementias

    PubMed Central

    Tripathi, Manjari; Vibha, Deepti

    2009-01-01

    In recent years, more attention has been given to the early diagnostic evaluation of patients with dementia which is essential to identify patients with cognitive symptoms who may have treatable conditions. Guidelines suggest that all patients presenting with dementia or cognitive symptoms should be evaluated with a range of laboratory tests, and with structural brain imaging with computed tomography (CT) or magnetic resonance imaging (MRI). While many of the disorders reported as ‘reversible dementias’ are conditions that may well be associated with cognitive or behavioral symptoms, these symptoms are not always sufficiently severe to fulfill the clinical criteria for dementia. Thus, while the etiology of a condition may be treatable it should not be assumed that the associated dementia is fully reversible. Potentially reversible dementias should be identified and treatment considered, even if the symptoms are not sufficiently severe to meet the clinical criteria for dementia, and even if partial or full reversal of the cognitive symptoms cannot be guaranteed. In the literature, the most frequently observed potentially reversible conditions identified in patients with cognitive impairment or dementia are depression, adverse effects of drugs, drug or alcohol abuse, space-occupying lesions, normal pressure hydrocephalus, and metabolic conditions land endocrinal conditions like hypothyroidism and nutritional conditions like vitamin B-12 deficiency. Depression is by far the most common of the potentially reversible conditions. The review, hence addresses the common causes of reversible dementia and the studies published so far. PMID:21416018

  2. Reversible Sterilization

    ERIC Educational Resources Information Center

    Largey, Gale

    1977-01-01

    Notes that difficult questions arise concerning the use of sterilization for alleged eugenic and euthenic purposes. Thus, how reversible sterilization will be used with relation to the poor, mentally ill, mentally retarded, criminals, and minors, is questioned. (Author/AM)

  3. Reversible Cardiomyopathies

    PubMed Central

    Patel, Harsh; Madanieh, Raef; Kosmas, Constantine E; Vatti, Satya K; Vittorio, Timothy J

    2015-01-01

    Cardiomyopathies (CMs) have many etiological factors that can result in severe structural and functional dysregulation. Fortunately, there are several potentially reversible CMs that are known to improve when the root etiological factor is addressed. In this article, we discuss several of these reversible CMs, including tachycardia-induced, peripartum, inflammatory, hyperthyroidism, Takotsubo, and chronic illness–induced CMs. Our discussion also includes a review on their respective pathophysiology, as well as possible management solutions. PMID:26052233

  4. Role of Glycoside Phosphorylases in Mannose Foraging by Human Gut Bacteria*

    PubMed Central

    Ladevze, Simon; Tarquis, Laurence; Cecchini, Davide A.; Bercovici, Juliette; Andr, Isabelle; Topham, Christopher M.; Morel, Sandrine; Laville, Elisabeth; Monsan, Pierre; Lombard, Vincent; Henrissat, Bernard; Potocki-Vronse, Gabrielle

    2013-01-01

    To metabolize both dietary fiber constituent carbohydrates and host glycans lining the intestinal epithelium, gut bacteria produce a wide range of carbohydrate-active enzymes, of which glycoside hydrolases are the main components. In this study, we describe the ability of phosphorylases to participate in the breakdown of human N-glycans, from an analysis of the substrate specificity of UhgbMP, a mannoside phosphorylase of the GH130 protein family discovered by functional metagenomics. UhgbMP is found to phosphorolyze ?-d-Manp-1,4-?-d-GlcpNAc-1,4-d-GlcpNAc and is also a highly efficient enzyme to catalyze the synthesis of this precious N-glycan core oligosaccharide by reverse phosphorolysis. Analysis of sequence conservation within family GH130, mapped on a three-dimensional model of UhgbMP and supported by site-directed mutagenesis results, revealed two GH130 subfamilies and allowed the identification of key residues responsible for catalysis and substrate specificity. The analysis of the genomic context of 65 known GH130 sequences belonging to human gut bacteria indicates that the enzymes of the GH130_1 subfamily would be involved in mannan catabolism, whereas the enzymes belonging to the GH130_2 subfamily would rather work in synergy with glycoside hydrolases of the GH92 and GH18 families in the breakdown of N-glycans. The use of GH130 inhibitors as therapeutic agents or functional foods could thus be considered as an innovative strategy to inhibit N-glycan degradation, with the ultimate goal of protecting, or restoring, the epithelial barrier. PMID:24043624

  5. Immunosuppressive C?? steroidal glycosides from the root of Cynanchum atratum.

    PubMed

    Zhang, Zhi-Jun; Ding, Mei-Ling; Tao, Li-Jun; Zhang, Mian; Xu, Xiang-Hong; Zhang, Chao-Feng

    2015-09-01

    Six new C21 steroidal glycosides (1-6) and one dideoxysaccharide (7), named atratcynosides A-F and atratcynose A, were isolated from the 80% ethanol extract of the root of Cynanchum atratum, together with three known compounds (8-10). The structures of the new compounds were determined on the basis of extensive spectral analyses and qualitative chemical methods. All compounds were subjected to detect the immunosuppressive activities by an in vitro model of concanavalin A-induced proliferation of T-lymphocytes from mice. Compounds 1-3 showed significant immunosuppressive activities in dose-dependent manners with the IC50 values from 3.3 to 7.0 ?M. Moreover, the structure-activity relationship of the steroidal glycosides on the immunosuppression was analyzed. PMID:26186991

  6. Novel Steroidal Glycosides from the Bulbs of Lilium pumilum.

    PubMed

    Matsuo, Yukiko; Takaku, Reina; Mimaki, Yoshihiro

    2015-01-01

    Examination of the bulbs of Lilium pumilum (Liliaceae) led to the isolation of four novel steroidal glycosides (1-4) with a 2,3,4-trisubstituted ?-d-glucopyranosyl unit. In 1 and 3, the ?-L-arabinopyranosyl moiety is linked to C-3 of the inner trisubstituted ?-D-glucopyranosyl group and is present as an usual ?C? conformation. In contrast, in 2 and 4, the ?-L-arabinopyranosyl moiety, which is attached to C-4 of the inner trisubstituted ?-D-glucopyranosyl group, is present as a C? conformation. The structures of the new steroidal glycosides were determined based on the results of spectroscopic analyses, including two-dimensional (2D) NMR data and hydrolysis. PMID:26370950

  7. Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.

    PubMed

    Iwadate, Takehiro; Kashiwakura, Yutaka; Masuoka, Noriyoshi; Yamada, Yoichi; Nihei, Ken-Ichi

    2014-01-01

    The concise synthesis of rhododendrol glycosides 3-8, which are novel derivatives of (+)-epirhododendrin (1) and (-)-rhododendrin (2), has been achieved in six steps from benzaldehyde 9. The key reactions include aldol condensation and trichloroacetimidate glycosylation. From biological studies, it has been determined that synthetic derivatives of 1 and 2 possess potent tyrosinase inhibitory activity. Particularly, the inhibitory activity of cellobioside 8 (IC50=1.51μM) is six times higher than that of kojic acid. The R-epimers (4, 6, and 8) possessed more potent activity than the corresponding S-epimers (3, 5, and 7), indicating that tyrosinase inhibitory activity is significantly governed by stereochemistry of rhododendrol glycosides. PMID:24332496

  8. Cytotoxic triterpene glycosides from the roots of Sanguisorba officinalis.

    PubMed

    Hu, Jiang; Song, Yan; Li, Hui; Yang, Benshou; Mao, Xia; Zhao, Yongmao; Shi, Xiaodong

    2015-06-01

    Phytochemical investigation of the ethanol extract of the roots of Sanguisorba officinalis resulted in the isolation of three new triterpene glycosides, 3β-[(α-L-arabinopyranosyl)oxy]-19α,23-dihydroxyolean-12-en-28-oic acid 28-[6-O-acetyl-β-D-glucopyranosyl] ester (1), 2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid 28-[6-O-acetyl-β-D-glucopyranosyl] ester (2), and 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyurs-12,20(30)-dien-28-oic acid 28-[6-O-acetyl-β-D-glucopyranosyl] ester (3). All the triterpene glycosides exhibited the significant cytotoxic potential with low IC50 values (IC50 < 5.0 μM) against six tumor cell lines (MCF-7, HeLa, HepG2, SGC-7901, NCI-H460, and BGC-823). PMID:25193625

  9. A new antioxidant flavone glycoside from Scutellaria baicalensis Georgi.

    PubMed

    Wang, Meng-Hua; Li, Lin-Zhen; Sun, Jian-Bo; Wu, Fei-Hua; Liang, Jing-Yu

    2014-01-01

    A new flavone glycoside, wogonin 7-O-?-D-ethylglucuronide (1), together with a new natural flavone glycoside baicalein 7-O-?-D-ethylglucuronide (2) and four known analogues, wogonoside (3), wogonin (4), oroxylin A 7-O-?-D-methylglucuronide (5) and oroxylin A (6), was isolated from the roots of Scutellaria baicalensis Georgi. The structure elucidation of the new compound was primarily based on HR-ESI-MS, 1D and 2D NMR analyses. Compounds 1 and 3 inhibited FeSO4-Cys-induced liver homogenate lipid peroxidation with IC50 at 18.2 ?M and 24.9 ?M, respectively, and exhibited strong cytoprotective effects against H2O2-induced oxidative damage in human umbilical vein endothelial cells at low concentrations of 10.0 ?M and 3.0 ?M. PMID:24995563

  10. Malonylated flavonol glycosides from the petals of Clitoria ternatea.

    PubMed

    Kazuma, Kohei; Noda, Naonobu; Suzuki, Masahiko

    2003-01-01

    Three flavonol glycosides, kaempferol 3-O-(2"-O-alpha-rhamnosyl-6"-O-malonyl)-beta-glucoside, quercetin 3-O-(2"-O-alpha-rhamnosyl-6"-O-malonyl)-beta-glucoside, and myricetin 3-O-(2",6"-di-O-alpha-rhamnosyl)-beta-glucoside were isolated from the petals of Clitoria ternatea cv. Double Blue, together with eleven known flavonol glycosides. Their structures were identified using UV, MS, and NMR spectroscopy. They were characterized as kaempferol and quercetin 3-(2(G)- rhamnosylrutinoside)s, kaempferol, quercetin, and myricetin 3-neohesperidosides, 3-rutinosides, and 3-glucosides in the same tissue. In addition, the presence of myricetin 3-O-(2"-O-alpha-rhamnosyl-6"-O-malonyl)-beta-glucoside was inferred from LC/MS/MS data for crude petal extracts. The flavonol compounds identified in the petals of C. ternatea differed from those reported in previous studies. PMID:12482461

  11. Antiviral glycosidic bisindole alkaloids from the roots of Isatis indigotica.

    PubMed

    Liu, Yu-Feng; Chen, Ming-Hua; Guo, Qing-Lan; Lin, Sheng; Xu, Cheng-Bo; Jiang, Yue-Ping; Li, Yu-Huan; Jiang, Jian-Dong; Shi, Jian-Gong

    2015-01-01

    Seven new glycosidic bisindole alkaloids, isatindigobisindolosides A-G (1-7), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including absolute configurations were determined by spectroscopic and chemical methods, together with calculations of electronic circular dichroism (ECD) spectra based on the quantum-mechanical time-dependent density functional theory. In the NMR spectra of 1-3, it is found that integration of H-2 and intensity of C-2 are affected not only by a substitution group at C-2 but also by solvents. Influences of the glucopyranosyloxy on the calculated ECD spectra of the glycosidic bisindole alkaloids are discussed. Compounds 2, 5, and 6 showed antiviral activity against both the influenza virus A/Hanfang/359/95 (H3N2) and Coxsackie virus B3 with IC50 values of 8.4-100.0?M. PMID:26123248

  12. Quinovic acid glycosides from roots of Macfadyena unguis-cati.

    PubMed

    Ferrari, F; Kiyan de Cornelio, I; Delle Monache, F; Marini Bettolo, G B

    1981-09-01

    Two glycosides, isolated in good yields from roots of Macfadyena unguis-cati (L.) A. G entry (syn. Doxantha unguis-cati (L.) Miers), gave on hydrolysis the same aglycone (quinovic acid). The sugar moieties have been identified as fucose and glucose respectively. This is the first time that saponins have been found in Bignoniaceae and their occurrence may account of the use of the plant in folk medicine. PMID:17402003

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

    PubMed

    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 17.9081.949?M. PMID:25367562

  14. New phenolic glycosides from the seeds of Cucurbita moschata.

    PubMed

    Li, Fa-Sheng; Dou, De-Qiang; Xu, Liang; Chi, Xiao-Feng; Kang, Ting-Guo; Kuang, Hai-Xue

    2009-07-01

    Two new phenolic glycosides were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as (2-hydroxy)phenylcarbinyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1) and 4-beta-D-(glucopyranosyl hydroxymethyl)phenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence. PMID:20183300

  15. Vina-Carb: Improving Glycosidic Angles during Carbohydrate Docking.

    PubMed

    Nivedha, Anita K; Thieker, David F; Makeneni, Spandana; Hu, Huimin; Woods, Robert J

    2016-02-01

    Molecular docking programs are primarily designed to align rigid, drug-like fragments into the binding sites of macromolecules and frequently display poor performance when applied to flexible carbohydrate molecules. A critical source of flexibility within an oligosaccharide is the glycosidic linkages. Recently, Carbohydrate Intrinsic (CHI) energy functions were reported that attempt to quantify the glycosidic torsion angle preferences. In the present work, the CHI-energy functions have been incorporated into the AutoDock Vina (ADV) scoring function, subsequently termed Vina-Carb (VC). Two user-adjustable parameters have been introduced, namely, a CHI- energy weight term (chi_coeff) that affects the magnitude of the CHI-energy penalty and a CHI-cutoff term (chi_cutoff) that negates CHI-energy penalties below a specified value. A data set consisting of 101 protein-carbohydrate complexes and 29 apoprotein structures was used in the development and testing of VC, including antibodies, lectins, and carbohydrate binding modules. Accounting for the intramolecular energies of the glycosidic linkages in the oligosaccharides during docking led VC to produce acceptable structures within the top five ranked poses in 74% of the systems tested, compared to a success rate of 55% for ADV. An enzyme system was employed in order to illustrate the potential application of VC to proteins that may distort glycosidic linkages of carbohydrate ligands upon binding. VC represents a significant step toward accurately predicting the structures of protein-carbohydrate complexes. Furthermore, the described approach is conceptually applicable to any class of ligands that populate well-defined conformational states. PMID:26744922

  16. Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius.

    PubMed

    Ozipek, Meltem; Dnmez, Ali A; Cali?, Ihsan; Brun, Reto; Redi, Peter; Tasdemir, Deniz

    2005-05-01

    Two new cycloartane-type glycosides oleifoliosides A (1) and B (2) were isolated from the lower stem parts of Astragalus oleifolius. Their structures were identified as 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-xylopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane and 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Three known cycloartane glycosides cyclocanthoside E (3), astragaloside II (4) and astragaloside IV (5) were also isolated and characterized. All five compounds were evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Except for the compound 5, all compounds showed notable growth inhibitory activity against Leishmania donovani with IC50 values ranging from 13.2 to 21.3 microg/ml. Only weak activity against Trypanosoma brucei rhodesiense was observed with the known compounds astragaloside II (4, IC50 66.6 microg/ml) and cyclocanthoside E (3, IC50 85.2 microg/ml), while all compounds were inactive against Trypanosoma cruzi and Plasmodium falciparum. None of the compounds were toxic to mammalian cells (IC50's > 90 microg/ml). This is the first report of leishmanicidal and trypanocidal activity of cycloartane-type triterpene glycosides. PMID:15922377

  17. Minor diterpene glycosides from the leaves of Stevia rebaudiana.

    PubMed

    Ibrahim, Mohamed A; Rodenburg, Douglas L; Alves, Kamilla; Fronczek, Frank R; McChesney, James D; Wu, Chongming; Nettles, Brian J; Venkataraman, Sylesh K; Jaksch, Frank

    2014-05-23

    Two new diterpene glycosides in addition to five known glycosides have been isolated from a commercial extract of the leaves of Stevia rebaudiana. Compound 1 (rebaudioside KA) was shown to be 13-[(O-?-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-?-d-glucopyranosyl-?-d-glucopyranosyl ester and compound 2, 12-?-[(2-O-?-d-glucopyranosyl-?-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid ?-d-glucopyranosyl ester. Five additional known compounds were identified, rebaudioside E, rebaudioside M, rebaudioside N, rebaudioside O, and stevioside, respectively. Enzymatic hydrolysis of stevioside afforded the known ent-kaurane aglycone 13-hydroxy-ent-kaur-16-en-19-oic acid (steviol) (3). The isolated metabolite 1 possesses the ent-kaurane aglycone steviol (3), while compound 2 represents the first example of the isomeric diterpene 12-?-hydroxy-ent-kaur-16-en-19-oic acid existing as a glycoside in S. rebaudiana. The structures of the isolated metabolites 1 and 2 were determined based on comprehensive 1D- and 2D-NMR (COSY, HSQC, and HMBC) studies. A high-quality crystal of compound 3 has formed, which allowed the acquisition of X-ray diffraction data that confirmed its structure. The structural similarities between the new metabolites and the commercially available stevioside sweeteners suggest the newly isolated metabolites should be examined for their organoleptic properties. Accordingly rebaudiosides E, M, N, O, and KA have been isolated in greater than gram quantities. PMID:24758242

  18. Sweet Poisons: Honeys Contaminated with Glycosides of the Neurotoxin Tutin.

    PubMed

    Larsen, Lesley; Joyce, Nigel I; Sansom, Catherine E; Cooney, Janine M; Jensen, Dwayne J; Perry, Nigel B

    2015-06-26

    Poisonings due to consumption of honeys containing plant toxins have been reported widely. One cause is the neurotoxin tutin, an oxygenated sesquiterpene picrotoxane, traced back to honeybees (Apis mellifera) collecting honeydew produced by passionvine hoppers (Scolypopa australis) feeding on sap of the poisonous shrub tutu (Coriaria spp.). However, a pharmacokinetic study suggested that unidentified conjugates of tutin were also present in such honeys. We now report the discovery, using ion trap LC-MS, of two tutin glycosides and their purification and structure determination as 2-(β-d-glucopyranosyl)tutin (4) and 2-[6'-(α-d-glucopyranosyl)-β-d-glucopyranosyl]tutin (5). These compounds were used to develop a quantitative triple quadrupole LC-MS method for honey analysis, which showed the presence of tutin (3.6 ± 0.1 μg/g honey), hyenanchin (19.3 ± 0.5), tutin glycoside (4) (4.9 ± 0.4), and tutin diglycoside (5) (4.9 ± 0.1) in one toxic honey. The ratios of 4 and 5 to tutin varied widely in other tutin-containing honeys. The glycosidation of tutin may represent detoxification by one or both of the insects involved in the food chain from plant to honey. PMID:25993882

  19. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives

    PubMed Central

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

    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, resveratrol 3,5-O-β-d-diglucoside, and resveratrol 3,5,4′-O-β-d-triglucoside. The conversion rates and numbers of products formed were found to vary with the other NDP sugar donors. Resveratrol 3-O-β-d-2-deoxyglucoside and resveratrol 3,5-O-β-d-di-2-deoxyglucoside were found to be produced using TDP-2-deoxyglucose as a donor; however, the monoglycosides resveratrol 4′-O-β-d-galactoside, resveratrol 4′-O-β-d-viosaminoside, resveratrol 3-O-β-l-rhamnoside, and resveratrol 3-O-β-l-fucoside were produced from the respective sugar donors. Altogether, 10 diverse glycoside derivatives of the medically important resveratrol were generated, demonstrating the capacity of YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

  20. Development and application of a screening assay for glycoside phosphorylases.

    PubMed

    De Groeve, M R M; Tran, G H; Van Hoorebeke, A; Stout, J; Desmet, T; Savvides, S N; Soetaert, W

    2010-06-01

    Glycoside phosphorylases (GPs) are interesting enzymes for the glycosylation of chemical molecules. They require only a glycosyl phosphate as sugar donor and an acceptor molecule with a free hydroxyl group. Their narrow substrate specificity, however, limits the application of GPs for general glycoside synthesis. Although an enzyme's substrate specificity can be altered and broadened by protein engineering and directed evolution, this requires a suitable screening assay. Such a screening assay has not yet been described for GPs. Here we report a screening procedure for GPs based on the measurement of released inorganic phosphate in the direction of glycoside synthesis. It appeared necessary to inhibit endogenous phosphatase activity in crude Escherichia coli cell extracts with molybdate, and inorganic phosphate was measured with a modified phosphomolybdate method. The screening system is general and can be used to screen GP enzyme libraries for novel donor and acceptor specificities. It was successfully applied to screen a residue E649 saturation mutagenesis library of Cellulomonas uda cellobiose phosphorylase (CP) for novel acceptor specificity. An E649C enzyme variant was found with novel acceptor specificity toward alkyl beta-glucosides and phenyl beta-glucoside. This is the first report of a CP enzyme variant with modified acceptor specificity. PMID:20188057

  1. A comparison of flavonoid glycosides by electrospray tandem mass spectrometry

    NASA Astrophysics Data System (ADS)

    March, Raymond E.; Lewars, Errol G.; Stadey, Christopher J.; Miao, Xiu-Sheng; Zhao, Xiaoming; Metcalfe, Chris D.

    2006-01-01

    A comparison is presented of product ion mass spectra of protonated and deprotonated molecules of kaempferol-3-O-glucoside, quercitin-3-O-glucoside (isoquercitrin), quercitin-3-O-galactoside (hyperoin), apigenin-7-O-glucoside, luteolin-7-O-glucoside, genistein-7-O-glucoside, naringenin-7-O-glucoside (prunin), luteolin-4'-O-glucoside, luteolin-6-C-glucoside (homoorientin, known also as isoorientin), apigenin-8-C-glucoside (vitexin), and luteolin-8-C-glucoside (orientin) together with the product ion mass spectrum of deprotonated kaempferol-7-O-glucoside. All isomeric ions were distinguishable on the basis of their product ion mass spectra. For protonated 3-O-, 7-O-, and 4'-O-glycosides at a collision energy of 46-47 eV, homolytic cleavage of the O-glycosidic bond yielded aglycon Y+ ions, whereas in deprotonated 3-O-, 7-O-, and 4'-O-glycosides, heterolytic and homolytic cleavage of the O-glycosidic bond yielded radical aglycon (Y-H)- and aglycon (Y-) ions. In each case, fragmentation of either the glycan or the aglycon or both was observed. For 6-C- and 8-C-glycosides at a collision energy of 46-47 eV, fragmentation was restricted almost exclusively to the glycan. For luteolin-6-C-glucoside, the integrity of the aglycon structure is preserved at the expense of the glycan for which some 30 fragmentations were observed. Breakdown curves were determined as a function of collision energy for protonated and deprotonated luteolin-6-C-glucoside. An attempt has been made to rationalize the product ion mass spectra derived from C-O- and C-C-luteolin glucosides in terms of computed structures that indicate significant intramolecular hydrogen bonding and rotation of the B-ring to form a coplanar luteolin structure. It is proposed that protonated and deprotonated luteolin-6-C-glucoside may afford examples of cooperative interactive bonding that plays a major role in directing fragmentation.

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

    PubMed Central

    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

  3. Isolation and characterization of stelladerol, a new antioxidant naphthalene glycoside, and other antioxidant glycosides from edible daylily (hemerocallis) flowers.

    PubMed

    Cichewicz, Robert H; Nair, Muraleedharan G

    2002-01-01

    Daylily (Hemerocallis spp.) flowers are utilized as an important ingredient in traditional Asian cuisine and are also valued for their reputed medicinal effects. In studies of the bioactive methanol and aqueous methanol extracts of lyophilized Hemerocallis cv. Stella de Oro flowers, kaempferol, quercetin, and isorhamnetin 3-O-glycosides (1-9), phenethyl beta-D-glucopyranoside (10), orcinol beta-D-glucopyranoside (11), phloretin 2'-O-beta-D-glucopyranoside (12), phloretin 2'-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (13), a new naphthalene glycoside, stelladerol (14), and an amino acid (longitubanine A) (15) have been isolated. All of these compounds were tested for their antioxidant and cyclooxygenase inhibitory activities. Stelladerol was found to possess strong antioxidant properties, inhibiting lipid oxidation by 94.6% +/- 1.4 at 10 microM in an in vitro assay. Several of the flavonol 3-O-glycoside isolates also demonstrated modest antioxidant activities at 10 microM. None of the isolates inhibited cyclooxygenase activity at 100 microM. PMID:11754548

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

    PubMed Central

    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, at the levels of the whole genome and 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. For several glycoside hydrolase familes (GH5, GH13, GH18, GH19, GH28, and GH51), we present a detailed literature review together with an examination of the family structures. This analysis of individual families revealed both similarities and distinctions between monocots and eudicots, as well as between species. Shared evolutionary histories appear to be modified by lineage-specific expansions or deletions. Within GH 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 grass model for investigations of these enzymes and their diverse roles in planta. Insights gained from Brachypodium will inform translational research studies, with applications for the improvement of cereal crops and bioenergy grasses. PMID:20973991

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

    SciTech Connect

    Tyler, Ludmila; Bragg, Jennifer; Wu, Jiajie; Yang, Xiaohan; Tuskan, Gerald A; Vogel, John

    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 gained from Brachypodium will inform translational research studies, with applications for the improvement of cereal crops and bioenergy grasses.

  6. Three new alkaloids and three new phenolic glycosides from Liparis odorata.

    PubMed

    Jiang, Piao; Liu, Hongdong; Xu, Xianghong; Liu, Bo; Zhang, Dongming; Lai, Xuewen; Zhu, Genghua; Xu, Peng; Li, Bin

    2015-12-01

    Three new alkaloids, liparis alkaloid A (1), B (2), C (3), and three new phenolic glycosides, liparis glycoside H (4), I (5), J (6), together with three known phenolic glycosides (7-9) were isolated from the whole plant of Liparis odorata. Their structures were characterized on the basis of extensive 1D-, 2D-NMR and HR-ESI-MS experiments. In addition, compounds 1-3 revealed hypolipidemic effects in the in vitro bioassays, and the ability to inhibit LPS-induced NO production of these isolated phenolic glycosides (4-9) was also evaluated. PMID:26481137

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

    PubMed Central

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

    2012-01-01

    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. PMID:23015769

  8. Vasectomy reversal.

    PubMed

    Belker, A M

    1987-02-01

    A vasovasostomy may be performed on an outpatient basis with local anesthesia, but also may be performed on an outpatient basis with epidural or general anesthesia. Local anesthesia is preferred by most of my patients, the majority of whom choose this technique. With proper preoperative and intraoperative sedation, patients sleep lightly through most of the procedure. Because of the length of time often required for bilateral microsurgical vasoepididymostomy, epidural or general anesthesia and overnight hospitalization are usually necessary. Factors influencing the preoperative choice for vasovasostomy or vasoepididymostomy in patients undergoing vasectomy reversal are considered. The preoperative planned choice of vasovasostomy or vasoepididymostomy for patients having vasectomy reversal described herein does not have the support of all urologists who regularly perform these procedures. My present approach has evolved as the data reported in Tables 1 and 2 have become available, but it may change as new information is evaluated. However, it offers a logical method for planning choices of anesthesia and inpatient or outpatient status for patients undergoing vasectomy reversal procedures. PMID:3811050

  9. Flavonoid glycoside: a new inhibitor of eukaryotic DNA polymerase alpha and a new carrier for inhibitor-affinity chromatography.

    PubMed

    Mizushina, Yoshiyuki; Ishidoh, Tomomi; Kamisuki, Shinji; Nakazawa, Satoshi; Takemura, Masaharu; Sugawara, Fumio; Yoshida, Hiromi; Sakaguchi, Kengo

    2003-02-01

    Two flavonoid glycosides, kaempferol 3-O-(6"-acetyl)-beta-glucopyranoside (KAG) and quercetin 3-O-(6"-acetyl)-beta-glucopyranoside (QAG), were found to be inhibitors of eukaryotic DNA polymerases from a Japanese vegetable, Petasites japonicus. These compounds inhibited the activities of mammalian replicative DNA polymerases (i.e., pol alpha, delta, and epsilon), but not other pol beta, eta, kappa, and lambda activities. KAG was a stronger inhibitor and more selective to pol alpha than QAG. The IC(50) values of KAG for pol alpha, delta, and epsilon were 41, 164, and 127 microM, respectively. The pol alpha inhibition by KAG was non-competitive with respect to both the DNA template-primer and the dNTP substrate. KAG and QAG did not influence the activities of prokaryotic DNA polymerases or other mammalian DNA metabolic enzymes such as human immunodeficiency virus type 1 reverse transcriptase, human telomerase, human DNA topoisomerase I and II, T7 RNA polymerase, and bovine deoxyribonuclease I. Therefore, we concluded that these flavonoid glycosides are moderate replicative DNA polymerase inhibitors leaning more relatively to pol alpha, and could be used as chromatographic carriers to purify the DNA polymerases rather than cytotoxic agents. We then made a KAG-conjugated column such as the epoxy-activated Sepharose 6B. In the column, pol alpha was selectively adsorbed and eluted. PMID:12565887

  10. Active site and laminarin binding in glycoside hydrolase family 55.

    PubMed

    Bianchetti, Christopher M; Takasuka, Taichi E; Deutsch, Sam; Udell, Hannah S; Yik, Eric J; Bergeman, Lai F; Fox, Brian G

    2015-05-01

    The Carbohydrate Active Enzyme (CAZy) database indicates that glycoside hydrolase family 55 (GH55) contains both endo- and exo-β-1,3-glucanases. The founding structure in the GH55 is PcLam55A from the white rot fungus Phanerochaete chrysosporium (Ishida, T., Fushinobu, S., Kawai, R., Kitaoka, M., Igarashi, K., and Samejima, M. (2009) Crystal structure of glycoside hydrolase family 55 β-1,3-glucanase from the basidiomycete Phanerochaete chrysosporium. J. Biol. Chem. 284, 10100-10109). Here, we present high resolution crystal structures of bacterial SacteLam55A from the highly cellulolytic Streptomyces sp. SirexAA-E with bound substrates and product. These structures, along with mutagenesis and kinetic studies, implicate Glu-502 as the catalytic acid (as proposed earlier for Glu-663 in PcLam55A) and a proton relay network of four residues in activating water as the nucleophile. Further, a set of conserved aromatic residues that define the active site apparently enforce an exo-glucanase reactivity as demonstrated by exhaustive hydrolysis reactions with purified laminarioligosaccharides. Two additional aromatic residues that line the substrate-binding channel show substrate-dependent conformational flexibility that may promote processive reactivity of the bound oligosaccharide in the bacterial enzymes. Gene synthesis carried out on ∼30% of the GH55 family gave 34 active enzymes (19% functional coverage of the nonredundant members of GH55). These active enzymes reacted with only laminarin from a panel of 10 different soluble and insoluble polysaccharides and displayed a broad range of specific activities and optima for pH and temperature. Application of this experimental method provides a new, systematic way to annotate glycoside hydrolase phylogenetic space for functional properties. PMID:25752603

  11. Three acylated flavone glycosides from Sideritis ozturkii Aytac & Aksoy.

    PubMed

    Sahin, F Pinar; Ta?demir, Deniz; Redi, Peter; Ezer, Nurten; Cali?, Ihsan

    2004-07-01

    From the aerial parts of Sideritis ozturkii, three new flavonoids, chrysoeriol 7-O-[2'''-O-caffeoyl-O-acetyl-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside], chrysoeriol 7-O[2'''-O-caffeoyl-beta-D-glucopyranosyl-(1 -->2)-beta-D-glucopyranoside] and chrysoeriol 7-O[2'''-O-p-coumaroyl-6'''-beta-O-acetyl-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside] named as ozturkosides A, B and C, respectively, were isolated, along with three known phenylethanoid glycosides, verbascoside, leucoseptoside A, martynoside and five known diterpenoids, 7-epicandicandiol, linearol, sidol, sideroxol, epoxyisolinearol. The structures were elucidated mainly by spectroscopic methods. PMID:15279978

  12. A new pregnane glycoside from Gomphocarpus fruticosus growing in Egypt.

    PubMed

    Marzouk, Amani M; Osman, Samir M; Gohar, Ahmed A

    2016-05-01

    Phytochemical investigation of Gomphocarpus fruticosus (L.) Ait. of Egyptian origin afforded the new pregnane glycoside lineolon-3-O-[β-D-oleandropyranosyl-(1-4)-β-D-cymaropyranosyl-(1-4)-β-D-cymaropyranoside], along with six known compounds. The structures of the isolated compounds were elucidated on the basis of extensive spectroscopic evidences derived from 1D, 2D NMR experiments, mass spectrometry and by comparing their physical and spectroscopic data to literature. These included the triterpenoids 3β-taraxerol, 3β-taraxerol acetate and betulinic acid, which are identified for the first time in G. fruticosus and the cardenolides uzarigenin, gomphoside and calotropin. PMID:26595507

  13. Additional new minor cucurbitane glycosides from Siraitia grosvenorii.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2014-01-01

    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 H- and C-NMR spectral assignments of the three unknown compounds are reported for the first time based on COSY, TOCSY, HSQC, and HMBC spectroscopic data. PMID:24662081

  14. A new alkaloid glycoside from the rhizomes of Aristolochia fordiana.

    PubMed

    Zhou, Zhongbo; Luo, Jianguang; Pan, Ke; Kong, Lingyi

    2014-01-01

    A new alkaloid glycoside named fordianoside (1), together with three known compounds arabinothalictoside (2), 6-O-p-coumaroyl-?-fructofuranosyl-(2?1)-?-d-glucopyranoside (3) and 4-[formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid (4), was isolated from the rhizomes of Aristolochia fordiana. The structure of 1 was established as (1S)-1,2,3,4-tetrahydro-7-hydroxy-1-[(4-hydroxybenzyl) methyl]-2,2-dimethyl-8-O-isoquinolinyl ?-d-glucopyranoside by using chemical and spectroscopic methods including HR-ESI-MS, 1D and 2D NMR. PMID:24716548

  15. Bioactive Iridoid Glycosides from the Whole Plants of Rehmannia chingii.

    PubMed

    Liu, Yan-Fei; Shi, Guo-Ru; Wang, Xin; Zhang, Chun-Lei; Wang, Yan; Chen, Ruo-Yun; Yu, De-Quan

    2016-02-26

    Nine new iridoid glycosides, rehmachingiiosides A-I (1-9), together with 16 known analogues, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of spectroscopic data analysis and from chemical evidence. Furthermore, in two vitro assays, compounds 5 and 10 showed an inhibitory effect on LPS-induced NO production with IC50 values of 2.5 and 7.3 ?M, and compounds 4, 6, and 10-12 (when evaluated at 10 ?M) exhibited evidence of hepatoprotective effects against APAP-induced HepG2 cell damage. PMID:26859776

  16. A new labdane diterpenoid glycoside from Nervilia fordii.

    PubMed

    Huang, Gui-Kun; Qiu, Li; Jiao, Yang; Xie, Ji-Zhao; Zou, Lu-Hui

    2014-05-01

    To study the chemical constituents of Nervilia fordii (Hance) Schltr., various chromatographic methods were used, including D101 macroporous resin, silica gel, ODS and preparative HPLC chromatographic techniques. A new labdane diterpenoid glycoside named as nervilifordoside A was isolated from 60% EtOH extract of Nerviliafordii. The structure of compound 1 was elucidated as 12, 17-epoxy-3-hydroxy-17-methoxy-labdan-13-en-16, 15-olide 3-O-alpha-rhamnopyranosyl-(1 --> 2)-O-beta-glucopyranoside on the basis of HR-MS, 1D and 2D NMR spectroscopic data as well as chemical methods. PMID:25151736

  17. Identification of proanthocyanidin dimers and trimers, flavone C-Glycosides, and antioxidants in Ficus deltoidea , a malaysian herbal tea.

    PubMed

    Omar, Maizatul Hasyima; Mullen, William; Crozier, Alan

    2011-02-23

    Phenolic compounds in an aqueous infusion of leaves of Ficus deltoidea (Moraceae), a well-known herbal tea in Malaysia, were analyzed by HPLC coupled to photodiode array and fluorescence detectors and an electrospray ionization tandem mass spectrometer. Following chromatography of extracts on a reversed phase C(12) column, 25 flavonoids were characterized and/or tentatively identified with the main constituents being flavan-3-ol monomers, proanthocyanidins, and C-linked flavone glycosides. The proanthocyanidins were dimers and trimers comprising (epi)catechin and (epi)afzelechin units. No higher molecular weight proanthocyanidin polymers were detected. The antioxidant activity of F. deltoidea extract was analyzed using HPLC with online antioxidant detection. This revealed that 85% of the total antioxidant activity of the aqueous F. deltoidea infusion was attributable to the flavan-3-ol monomers and the proanthocyanidins. PMID:21261251

  18. Mechanisms and energetics for N-glycosidic bond cleavage of protonated 2'-deoxyguanosine and guanosine.

    PubMed

    Wu, R R; Chen, Yu; Rodgers, M T

    2016-01-20

    Experimental and theoretical investigations suggest that hydrolysis of N-glycosidic bonds generally involves a concerted SN2 or a stepwise SN1 mechanism. While theoretical investigations have provided estimates for the intrinsic activation energies associated with N-glycosidic bond cleavage reactions, experimental measurements to validate the theoretical studies remain elusive. Here we report experimental investigations for N-glycosidic bond cleavage of the protonated guanine nucleosides, [dGuo+H](+) and [Guo+H](+), using threshold collision-induced dissociation (TCID) techniques. Two major dissociation pathways involving N-glycosidic bond cleavage, resulting in production of protonated guanine or the elimination of neutral guanine are observed in competition for both [dGuo+H](+) and [Guo+H](+). The detailed mechanistic pathways for the N-glycosidic bond cleavage reactions observed are mapped via electronic structure calculations. Excellent agreement between the measured and B3LYP calculated activation energies and reaction enthalpies for N-glycosidic bond cleavage of [dGuo+H](+) and [Guo+H](+) in the gas phase is found indicating that these dissociation pathways involve stepwise E1 mechanisms in analogy to the SN1 mechanisms that occur in the condensed phase. In contrast, MP2 is found to significantly overestimate the activation energies and slightly overestimate the reaction enthalpies. The 2'-hydroxyl substituent is found to stabilize the N-glycosidic bond such that [Guo+H](+) requires ?25 kJ mol(-1) more than [dGuo+H](+) to activate the glycosidic bond. PMID:26740232

  19. Three new iridoid glycosides from the fruit of gardenia jasminoides var. radicans.

    PubMed

    Qin, Fang-Min; Meng, Ling-Jie; Zou, Hui-Liang; Zhou, Guang-Xiong

    2013-01-01

    Three new iridoid glycosides, 6?-O-trans-feruloylgenipin gentiobioside (1), 2'-O-trans-p-coumaroylgardoside (2), 2'-O-trans-feruloylgardoside (3), were isolated from the fruit of Gardenia jasminoides var. radicans MAKINO (Rubiaceae). The structures of these compounds were elucidated on the basis of MS, NMR spectra analysis, glycoside hydrolysis, and sugar derivatization coupled with HPLC analysis. PMID:24088698

  20. Environment and Genotype Affect Sweetpotato Storage Root Periderm Resin Glycoside Content

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Resin glycosides are complex compounds composed primarily of fatty acids and sugars that contribute to allelopathic potential and pest resistance in sweetpotato. Total periderm resin glycoside (PRG) contents of 10 sweetpotato (Ipomoea batatas L.) clones grown in three different field trials was det...

  1. Species and ionic influences on the accumulation of digitalis glycosides by isolated perfused hearts

    PubMed Central

    Dutta, S.; Marks, B. H.

    1972-01-01

    1. The ability of isolated perfused guinea-pig (digitalis-sensitive species) and rat (digitalis-resistant species) hearts to accumulate radio-labelled digitalis glycosides was studied in relation to the ionic composition of the perfusion medium. 2. It was observed that in both species much less digoxin was accumulated than was digitoxin or proscillaridin. 3. The accumulation of digoxin was markedly inhibited in a low sodium or in high potassium medium. These effects were similar, but relatively less marked, with digitoxin and proscillaridin. Calcium and magnesium removal had relatively smaller effects on the accumulation of both polar and non-polar glycosides. 4. The low accumulation of all digitaloids by the rat heart in comparison to the guinea-pig heart may be due to the formation of unstable complexes between the cellular membranes in the rat heart and the various digitaloids used in this study. Although digitaloids have a reduced affinity for rat hearts and rat heart membranes in comparison to guinea-pigs, the order of the accumulation of different glycosides in both species is the same, i.e. much less with polar glycosides than with non-polar glycosides. 5. It was concluded that non-polar glycosides such as digitoxin and proscillaridin demonstrate the same ion-dependent accumulation mechanism as do the more polar glycosides such as digoxin and ouabain. In addition, the non-polar glycosides possess high capacity for ion-independent binding presumably due to lipophilic interactions with membranes. PMID:4656603

  2. Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β-C-Glycosides.

    PubMed

    Guisot, Nicolas E S; Ella Obame, Idriss; Ireddy, Prathap; Nourry, Arnaud; Saluzzo, Christine; Dujardin, Gilles; Dubreuil, Didier; Pipelier, Muriel; Guillarme, Stéphane

    2016-03-18

    A new strategy for the synthesis of acyl β-C-glycosides is described. The reactivity of glyconitriles toward organometallic reagents such as organomagnesium or organolithium derivatives was studied, affording acyl β-C-glycosides in moderate to good yields. In this study, glycal formation was efficiently prevented by deprotonating the hydroxyl group in position 2 of the glyconitriles during the process. PMID:26926714

  3. Phenylethanoid glycosides of Pedicularis muscicola Maxim ameliorate high altitude-induced memory impairment.

    PubMed

    Zhou, Baozhu; Li, Maoxing; Cao, Xinyuan; Zhang, Quanlong; Liu, Yantong; Ma, Qiang; Qiu, Yan; Luan, Fei; Wang, Xianmin

    2016-04-01

    Exposure to hypobaric hypoxia causes oxidative stress, neuronal degeneration and apoptosis that leads to memory impairment. Though oxidative stress contributes to neuronal degeneration and apoptosis in hypobaric hypoxia, the ability for phenylethanoid glycosides of Pedicularis muscicola Maxim (PhGs) to reverse high altitude memory impairment has not been studied. Rats were supplemented with PhGs orally for a week. After the fourth day of drug administration, rats were exposed to a 7500m altitude simulation in a specially designed animal decompression chamber for 3days. Spatial memory was assessed by the 8-arm radial maze test before and after exposure to hypobaric hypoxia. Histological assessment of neuronal degeneration was performed by hematoxylin-eosin (HE) staining. Changes in oxidative stress markers and changes in the expression of the apoptotic marker, caspase-3, were assessed in the hippocampus. Our results demonstrated that after exposure to hypobaric hypoxia, PhGs ameliorated high altitude memory impairment, as shown by the decreased values obtained for reference memory error (RME), working memory error (WME), and total error (TE). Meanwhile, administration of PhGs decreased hippocampal reactive oxygen species levels and consequent lipid peroxidation by elevating reduced glutathione levels and enhancing the free radical scavenging enzyme system. There was also a decrease in the number of pyknotic neurons and a reduction in caspase-3 expression in the hippocampus. These findings suggest that PhGs may be used therapeutically to ameliorate high altitude memory impairment. PMID:26825251

  4. RP-HPLC analysis of seco-iridoid glycoside swertiamarin from different Swertia species.

    PubMed

    Kshirsagar, Parthraj R; Pai, Sandeep R; Nimbalkar, Mansingraj S; Gaikwad, Nikhil B

    2016-04-01

    Genus Swertia is valued for its great medicinal potential; mainly Swertia chirayita (Roxb. ex Fleming) H. Karst. is used in traditional medicine for a wide range of diseases. Seco-iridoid glycosides like swertiamarin is referred with enormous pharmacological potentials. The aim of the study was to identify a suitable substitute to S. chirayita by quantifying seco-iridoid swertiamarin from five different Swertia species endemic to the Western Ghats. The reverse-phase high-performance liquid chromatography diode array detector analyses were performed and chromatographic separation was achieved on a Lichrospher 100, C18e (5 µm) column (250-4.6 mm). A mobile phase consisting of acetonitrile and water (25:75) was used for separation. Results indicated that the concentration of the marker compound has been found to vary largely between and within the species from different localities. The content of swertiamarin was the highest in S. chirayita compared to the other species studied herein, advocating the use of Swertia minor as an alternate source to S. chirayita. PMID:26299409

  5. Triterpenoid glycosides from the leaves of two cultivars of Medicago polymorpha L.

    PubMed

    Tava, Aldo; Pecetti, Luciano; Romani, Massimo; Mella, Mariella; Avato, Pinarosa

    2011-06-01

    The saponin composition of leaves from the Medicago polymorpha cultivars 'Santiago' and 'Anglona' belonging to the botanical varieties brevispina and vulgaris, respectively, was investigated by a combination of chromatographic, spectroscopic, and spectrometric techniques. Several compounds were detected and quantitated by HPLC analysis using the external standard method. Twelve triterpene saponins (1-12) were purified by reverse-phase chromatography and their structures elucidated by spectroscopic (1D and 2D NMR, ESI-MS/MS) and chemical methods. They were identified as glycosides of echinocystic acid, hederagenin, caulophyllogenin, bayogenin, and soyasapogenol B. Two of them (2, 10) were previously reported in M. polymorpha; five of them (4, 6, 7, 9, 12) were already identified in other Medicago species; and three of them (1, 8, 11) were found in other plant genera. The two saponins identified as 3-O-α-L-arabinopyranosyl-28-O-[β-D-glucopyranosyl(1→6)β-D-glucopyranoside] echinocystic acid (3) and 3-O-α-L-arabinopyranosyl-28-O-β-D-glucopyranoside echinocystic acid (5) are newly identified natural compounds. The presence of echinocystic acid is reported here for the first time in the genus Medicago. Saponins from the cultivar 'Anglona' were characterized by a higher amount of echinocystic acid glycosydes, whereas saponins from the cultivar 'Santiago' were characterized by a higher amount of hederagenin glycosydes. PMID:21526796

  6. Resin glycosides from Ipomoea wolcottiana as modulators of the multidrug resistance phenotype in vitro.

    PubMed

    Corona-Castañeda, Berenice; Rosas-Ramírez, Daniel; Castañeda-Gómez, Jhon; Aparicio-Cuevas, Manuel Alejandro; Fragoso-Serrano, Mabel; Figueroa-González, Gabriela; Pereda-Miranda, Rogelio

    2016-03-01

    Recycling liquid chromatography was used for the isolation and purification of resin glycosides from the CHCl3-soluble extracts prepared using flowers of Ipomoea wolcottiana Rose var. wolcottiana. Bioassay-guided fractionation, using modulation of both antibiotic activity against multidrug-resistant strains of Gram-negative bacteria and vinblastine susceptibility in breast carcinoma cells, was used to isolate the active glycolipids as modulators of the multidrug resistance phenotype. An ester-type dimer, wolcottine I, one tetra- and three pentasaccharides, wolcottinosides I-IV, in addition to the known intrapilosin VII, were characterized by NMR spectroscopy and mass spectrometry. In vitro assays established that none of these metabolites displayed antibacterial activity (MIC>512μg/mL) against multidrug-resistant strains of Escherichia coli, and two nosocomial pathogens: Salmonella enterica serovar Typhi and Shigella flexneri; however, when tested (25μg/mL) in combination with tetracycline, kanamycin or chloramphenicol, they exerted a potentiation effect of the antibiotic susceptibility up to eightfold (64μg/mL from 512μg/mL). It was also determined that these non-cytotoxic (CI50>8.68μM) agents modulated vinblastine susceptibility at 25μg/mL in MFC-7/Vin(+) cells with a reversal factor (RFMCF-7/Vin(+)) of 2-130 fold. PMID:26774597

  7. Host plant influences on iridoid glycoside sequestration of generalist and specialist caterpillars.

    PubMed

    Lampert, Evan C; Bowers, M Deane

    2010-10-01

    The effect of diet on sequestration of iridoid glycosides was examined in larvae of three lepidopteran species. Larvae were reared upon Plantago major, or P. lanceolata, or switched from one to the other in the penultimate instar. Junonia coenia is a specialist on iridoid glycoside-producing plants, whereas the arctiids, Spilosoma congrua and Estigmene acrea, are both polyphagous and eat iridoid-producing plants. All species sequestered iridoids. The specialist J. coenia sequestered from three to seven times the amounts sequestered by the two generalist species. Junonia coenia iridoid glycoside content depended on diet, and they sequestered from 5 to 15% dry weight iridoid glycosides. Estigmene acrea iridoid glycoside sequestration was relatively low, around 2% dry weight and did not vary with diet. Spilosoma congrua sequestration varied with diet and ranged from approximately 3 to 6% dry weight. PMID:20809144

  8. Reversible hypogammaglobulinaemia.

    PubMed

    Desar, I M E; Weemaes, C M R; van Deuren, M; van der Meer, J W M

    2007-11-01

    In this report we present four patients with reversible hypogammaglobulinaemia who required immunoglobulin substitution for several years. One patient had documented systemic lupus erythematosus (SLE), the other three patients had primary hypogammaglobulinaemia without known cause. Whereas the cessation of azathioprine therapy may have contributed to the recovery in the patient with SLE, the restoration of the immunoglobulin production in the other three patients occurred spontaneously. All four patients were IgA deficient when the hypogammaglobulinaemia was first detected and remained so after IgM and IgG production had recovered. Two of the three patients who also had anti-IgA antibodies started to produce anti-IgA again after stopping the immunoglobulin substitution. We conclude that recovery of hypogammaglobulinaemia is possible but rare. When recovery is suspected, we recommend that immunoglobulin substitution is stopped and the antibody response to vaccination is tested. PMID:18057460

  9. Steviol Glycosides Modulate Glucose Transport in Different Cell Types

    PubMed Central

    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

  10. Cycloartane and oleanane-type glycosides from Astragalus pennatulus.

    PubMed

    Un, Rabia; Horo, Ibrahim; Masullo, Milena; Falco, Antonia; Senol, Serdar G; Piacente, Sonia; Alanku?-al?skan, zgen

    2016-03-01

    Four new cycloartane and one new oleanane-type glycosides were isolated from Astragalus pennatulus along with five known cycloartane-type glycosides. The structures of the new compounds were established as 3-O-?-D-xylopyranosyl-6-O-?-D-glucopyranosyl-3?,6?,16?-trihydroxy-24-oxo-20(R),25-epoxycycloartane (1), 3-O-[?-D-glucuronopyranosyl-(1?2)-?-D-xylopyranosyl]-3?,16?,24?-trihydroxy-20(R),25-epoxycycloartane (2), 3-O-[?-D-glucuronopyranosyl-(1?2)-?-D-xylopyranosyl]-3?,16?,25-trihydroxy-20(R),24(S)-epoxycycloartane (3), 3,25-di-O-?-D-glucopyranosyl-6-O-?-D-xylopyranosyl-3?,6?,16?,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), 29-O-?-L-rhamnopyranosyl-abrisapogenol B (5) by 1D and 2D-NMR experiments along with ESIMS and HRMS analyses. The aglycone of compound 1, 3?,6?,16?-trihydroxy-24-oxo-20(R),25-epoxycycloartane, is reported for the first time. The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. None of the tested compounds caused a significant reduction of the cell number. PMID:26804373

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

    PubMed

    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. PMID:24983351

  12. Syntheses of alpha-tocopheryl glycosides by glucosidases.

    PubMed

    Ponrasu, Thangavel; Charles, Rajachristu Einstein; Sivakumar, Ramaiah; Divakar, Soundar

    2008-08-01

    Enzymatic syntheses of water-soluble alpha-tocopheryl glycosides were carried out in di-isopropyl ether using amyloglucosidase from Rhizopus mold or beta-glucosidase isolated from sweet almond. Optimum conditions for the amyloglucosidase were: alpha-tocopherol 0.5 mmol, D-glucose 0.5 mmol, 400 activity unit (AU) amyloglucosidase, 0.2 mM pH 7 phosphate buffer and 72 h; and for the beta-glucosidase: alpha-tocopherol 0.5 mmol, D: -glucose 0.5 mmol, 110 AU beta-glucosidase, 0.1 mM pH 6 phosphate buffer and 72 h. Out of 11 carbohydrates employed, amyloglucosidase reacted only with D-glucose to give 50% of 6-O-(alpha-D-glucopyranosyl)alpha-tocopherol. However, the beta-glucosidase gave 6-O-(beta-D-glucopyranosyl)alpha-tocopherol, 6-O-(alpha-D-galactopyranosyl)alpha-tocopherol, 6-O-(beta-D-galactopyranosyl)alpha-tocopherol, 6-O-(alpha-D-mannopyranosyl)alpha-tocopherol and 6-O-(beta-D-mannopyranosyl)alpha-tocopherol in yields ranging from 10-25%. Water solubility of 6-O-(alpha-D-glucopyranosyl)alpha-tocopherol was 26 g/l at 25 degrees C. alpha-Tocopheryl glycosides showed antioxidant activities with IC(50) values from 0.5 to 1 mM and angiotensin-converting enzyme (ACE) inhibitory activity with IC(50) values from 1.3 to 2.6 mM. PMID:18368294

  13. C14-polyacetylenol glycosides from the roots of Codonopsis pilosula.

    PubMed

    Jiang, Yue-Ping; Liu, Yu-Feng; Guo, Qing-Lan; Shi, Jian-Gong

    2015-12-01

    Eight new C14-polyacetylenol glycosides, containing ene-diyne and ene-yn-ene chromophores named codonopilodiynosides H-M (1-6) and codonopiloenynenosides A and B (7 and 8), respectively, together with three known analogs lobetyolinin, pratialin B, and lobetyolin (9-11), were isolated from an aqueous extract of the roots of Codonopsis pilosula. Their structures were determined by spectroscopic and chemical methods including 2D NMR data analysis and enzymatic hydrolysis. The absolute configurations of aglycones in 1-10 were assigned by application of the methoxyphenylacetic acid (MPA) determination rule of ??(RS) values and/or the empirical rule of Mo2(OAc)4-induced circular dichroism for the vicinal diols, or by comparison of specific rotation values with those of reported compounds. Compounds 4-6 are the first polyacetylenol glycosides possessing a cis-ene-diyne chromophore from the genus Codonopsis, while 8 has a rear trans-ene-yn-cis-ene chromophore and a (6S,7S)-6,7-diol unit against a (6R,7R)-6,7-diol unit in the others. The absolute configurations of lobetyolinin (9) and pratialin B (10) were determined for the first time. PMID:26595102

  14. Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities.

    PubMed

    Bttcher, Stephan; Thiem, Joachim

    2015-01-01

    Indoxyl glycosides proved to be valuable and versatile tools for monitoring glycosidase activities. Indoxyls are released by enzymatic hydrolysis and are rapidly oxidized, for example by atmospheric oxygen, to indigo type dyes. This reaction enables fast and easy screening in vivo without isolation or purification of enzymes, as well as rapid tests on agar plates or in solution (e.g., blue-white screening, micro-wells) and is used in biochemistry, histochemistry, bacteriology and molecular biology. Unfortunately the synthesis of such substrates proved to be difficult, due to various side reactions and the low reactivity of the indoxyl hydroxyl function. Especially for glucose type structures low yields were observed. Our novel approach employs indoxylic acid ester as key intermediates. Indoxylic acid esters with varied substitution patterns were prepared on scalable pathways. Phase transfer glycosylations with those acceptors and peracetylated glycosyl halides can be performed under common conditions in high yields. Ester cleavage and subsequent mild silver mediated glycosylation yields the peracetylated indoxyl glycosides in high yields. Finally deprotection is performed according to Zempln. PMID:26068577

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

    PubMed

    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. PMID:24123550

  16. Angling for Uniqueness in Enzymatic Preparation of Glycosides

    PubMed Central

    Trincone, Antonio

    2013-01-01

    In the early days of biocatalysis, limitations of an enzyme modeled the enzymatic applications; nowadays the enzyme can be engineered to be suitable for the process requirements. This is a general birds-eye view and as such cannot be specific for articulated situations found in different classes of enzymes or for selected enzymatic processes. As far as the enzymatic preparation of glycosides is concerned, recent scientific literature is awash with examples of uniqueness related to the features of the biocatalyst (yield, substrate specificity, regioselectivity, and resistance to a particular reaction condition). The invention of glycosynthases is just one of the aspects that has thrust forward the research in this field. Protein engineering, metagenomics and reaction engineering have led to the discovery of an expanding number of novel enzymes and to the setting up of new bio-based processes for the preparation of glycosides. In this review, new examples from the last decade are compiled with attention both to cases in which naturally present, as well as genetically inserted, characteristics of the catalysts make them attractive for biocatalysis. PMID:24970171

  17. A new glycosidic flavonoid from Jwarhar mahakashay (antipyretic) Ayurvedic preparation

    PubMed Central

    Gupta, Mradu; Shaw, B. P.; Mukherjee, A.

    2010-01-01

    The aqueous extract of Jwarhar mahakashay Ayurvedic preparation (from the roots of Hemidesmus indicus R. Br., Rubia cordifolia L., Cissampelos pareira L.; fruits of Terminalia chebula Retz., Emblica officinalis Gaertn., Terminalia bellirica Roxb., Vitis vinifera L., Grewia asiatica L., Salvadora persica L. and granules of Saccharum officinarum L.) has been used as a traditional antipyretic. Experimental studies confirmed its antipyreticanalgesic effect with very low ulcerogenicity and toxicity. Flavonoids, glycosides and tannins were later found to be present in the extract. Detailed chemical investigations were undertaken after hydrolysis of extract using spectroscopic and chromatography methods to determine its active chemical constituent. UV-Visible spectroscopy showed absorbance maxima at 220 and 276 nm, while fourier transform infra-red investigations indicated an end carboxylic OH structure at 2940 cm?1 suggesting the presence of glycoside-linked flavonoids. Thin layer chromatography and high performance liquid chromatography also confirmed the possibility of at least one major and two minor compounds in this abstract. Detailed examination using gas chromatography-mass spectrometry led to the identification of the principal component as 2-(1-oxopropyl)-benzoic acid, which is quite similar to the active compound found in the standard drug Aspirin (2-acetyl-oxybenzoic acid). PMID:20814525

  18. Two new flavonol glycosides from Epimedium koreanum Nakai.

    PubMed

    Jiang, Fang; Wang, Xin-Luan; Wang, Nai-Li; Yao, Xin-Sheng

    2009-01-01

    Two new flavonol glycosides, named icarisid B (1) and icarisid C (2), along with seven known flavonol glycosides were isolated from the bioassay-directed fractions of the aqueous extract of Epimedium koreanum Nakai. The structures of the two new compounds were established on the basis of chemical and spectroscopic methods (ESI-MS, 1D, and 2D NMR) as 5-hydroxyl-4'-methoxy-8-(gamma-hydroxyl-gamma,gamma-dimethyl)-propyl-3-O-alpha-L-rhamnopyranosyl-flavonol-7-O-beta-D-glucopyranoside (1) and 5-hydroxyl-4'-methoxy-8-(gamma-methoxy-gamma,gamma-dimethyl)-propyl-3-O-beta-D-glucopyranosyl(1 --> 3)-alpha-L-rhamnopyranosyl-flavonol-7-O-beta-D-glucopyranoside (2), respectively. All the nine compounds were tested for their effects on proliferation and alkaline phosphatase (ALP) activity using UMR106 cells. As a result, five compounds showed stimulating effects on both the proliferation and ALP activity, which suggested that they might be used as potential leading compounds to cure osteoporosis. PMID:19504382

  19. Prenylflavonol, acylated flavonol glycosides and related compounds from Epimedium sagittatum.

    PubMed

    Wang, Guei-Jane; Tsai, Tung-Hu; Lin, Lie-Chwen

    2007-10-01

    Chemical examination of the n-BuOH extract from the aerial parts of Epimedium sagittatum led to isolation of three prenylated flavonol glycosides sagittasine A-C, two acylated flavonol glycosides kaempferol-3-O-(2''-E-p-coumaroyl,4''-Z-p-coumaroyl)-alpha-l-rhamnopyranoside and kaempferol-3-O-(3''-Z-p-coumaroyl,4''-E-p-coumaroyl)-alpha-l-rhamnopyranoside, together with known flavonoids, flavonolignans, 2-phenoxychromones, a lignan, and aromatic acid derivatives. Flavonolignans were identified for the first time in this plant. The vasorelaxing properties of the n-BuOH extract of E. sagittatum and 13 isolated compounds were tested using pre-contracted rat aorta rings in an organ bath apparatus. The results indicated that the n-BuOH extract of E. sagittatum produced a partial endothelial nitric oxide-dependent vasorelaxation, with EC(50) of 0.16+/-0.03 mg/ml. However, the 13 compounds tested, generated only a mild or moderate relaxation, and did not possess significant vasorelaxing effect individually. PMID:17618659

  20. Evaluation of the content variation of anthraquinone glycosides in rhubarb by UPLC-PDA

    PubMed Central

    2013-01-01

    Background Rhubarb is an important Chinese medicinal herb with a long history of over 2000 years and has been commonly used as a laxative. It is the radix and rhizome of Rheum officinale Baill., R. palmatum L. and R. tanguticum Maxim, all of which are mainly distributed in a broad region in the Tibetan plateau. Anthraquinone glycosides are a series of major active ingredients found in all three species. They are key intermediates in the anthraquinone secondary metabolism and the sennnoside biosynthesis. The variation of the anthraquinone glycoside content in rhubarb in response to specific factors remains an attractive topic. Results A simple and sensitive Ultra Performance Liquid Chromatography with Photo-Diode Array (UPLC-PDA) detector was developed for the simultaneous determination of six anthraquinone glycosides in rhubarb, i.e., aloeemodin-8-O-glucoside, rhein-8-O-glucoside, chrysophanol-1-O-glucoside, emodin-1-O-glucoside, chrysophanol-8-O-glucoside, emodin-8-O-glucoside. Twenty-seven batches from three species were submitted to the multi-component analysis. The results showed that the anthraquinone glycoside content varied significantly even within the same species. The results showed that the anthraquinone glycoside content varied significantly within the same species but not between different species. The PCA and content analysis results confirmed that the plant species has no obvious effect on the content variation. Neither was any significant correlation observed between the anthraquinone glycoside content and the geographic distribution of the rhubarb. Through correlational analysis, altitude was found to be the main factor that affects the anthraquinone glycoside content in rhubarb. Rhubarb grown at higher altitude has higher anthraquinone glycoside content. Conclusions This work provides a rapid, sensitive and accurate UPLC-PDA method for the simultaneous determination of six anthraquinone glycosides in rhubarb. The anthraquinone glycoside content varied significantly within the same species. The relationship of the anthraquinone glycoside content with plant species, geographic distribution and altitude were studied using correlational analysis, principal component analysis and spatial autocorrelation analysis through SPSS and ArcGIS. Plant species and geographic distribution were found not to affect the content of the six anthraquinone glycosides in rhubarb. The variations in the anthraquinone glycoside content were primarily due to the different altitude where the plant was grown. PMID:24160332

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

    PubMed

    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. PMID:26937589

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

    PubMed

    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. PMID:25631395

  3. Additional minor diterpene glycosides from Stevia rebaudiana Bertoni.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2013-01-01

    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-{?-D-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {?-D-xylopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)]-O-?-D-glucupyranosyl-ester} (1), and 13-{?-D-6-deoxy-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {?-D-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-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. PMID:24184820

  4. Two new lignan glycosides from the seeds of Cuscuta chinensis.

    PubMed

    He, Xiang-Hui; Yang, Wen-Zhi; Meng, A-Hui; He, Wen-Ni; Guo, De-An; Ye, Min

    2010-11-01

    Two new lignan glycosides, 2'-hydroxyl asarinin 2'-O-β-D-glucopyranoside (cuscutoside C, 1) and 2'-hydroxyl asarinin 2'-O-β-D-apiofuranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranoside (cuscutoside D, 2), were isolated from the seeds of Cuscuta chinensis Lam., along with six known compounds, 2'-hydroxyl asarinin 2'-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (3), 2'-hydroxyl asarinin 2'-O-β-D-apiofuranosyl-(1 → 2)-β-D-glucopyranoside (cuscutoside A, 4), kaempferol 3,7-di-O-β-D-glucopyranoside (5), 5-caffeoyl quinic acid (6), 4-caffeoyl quinic acid (7), and cinnamic acid (8). Their structures were elucidated on the basis of spectroscopic analyses including HR-ESI-MS, ESI-MS/MS, (1)H and (13)C NMR, HSQC, HMBC, and TOCSY. PMID:21061214

  5. Enzymatic hydrolysis of steryl glycosides for their analysis in foods.

    PubMed

    Münger, Linda H; Nyström, Laura

    2014-11-15

    Steryl glycosides (SG) contribute significantly to the total intake of phytosterols. The standard analytical procedure involving acid hydrolysis fails to reflect the correct sterol profile of SG due to isomerization of some of the labile sterols. Therefore, various glycosylases were evaluated for their ability to hydrolyse SG under milder conditions. Using a pure SG mixture in aqueous solution, the highest glycolytic activity, as demonstrated by the decrease in SG and increase in free sterols was achieved using inulinase preparations (decrease of >95%). High glycolytic activity was also demonstrated using hemicellulase (63%). The applicability of enzymatic hydrolysis using inulinase preparations was further verified on SG extracted from foods. For example in potato peel Δ(5)-avenasteryl glucoside, a labile SG, was well preserved and contributed 26.9% of the total SG. Therefore, enzymatic hydrolysis is suitable for replacing acid hydrolysis of SG in food lipid extracts to accurately determine the sterol profile of SG. PMID:24912717

  6. Methylated anthocyanidin glycosides from flowers of Canna indica.

    PubMed

    Srivastava, Jyoti; Vankar, Padma S

    2010-09-23

    Methylated anthocyanin glycosides were isolated from red Canna indica flower and identified as malvidin 3-O-(6-O-acetyl-beta-d-glucopyranoside)-5-O-beta-d-glucopyranoside (1), malvidin 3,5-O-beta-d-diglucopyranoside (2), cyanidin-3-O-(6''-O-alpha-rhamnopyranosyl-beta-glucopyranoside (3), cyanidin-3-O-(6''-O-alpha-rhamnopyranosyl)-beta-galactopyranoside (4), cyanidin-3-O-beta-glucopyranoside (5) and cyanidin-O-beta-galactopyranoside (6) by HPLC-PDA. Their structures were subsequently determined on the basis of spectroscopic analyses, that is, (1)H NMR, (13)C NMR, HMQC, HMBC, ESI-MS, and UV-vis. Compounds (1-4) were found to be in major quantity while compounds (5-6) were in minor quantity. PMID:20692649

  7. Tigliane-type diterpenoid glycosides from Euphorbia fischeriana.

    PubMed

    Pan, Li-Li; Fang, Ping-Lei; Zhang, Xing-Jie; Ni, Wei; Li, Lei; Yang, Liu-Meng; Chen, Chang-Xiang; Zheng, Yong-Tang; Li, Chang-Tian; Hao, Xiao-Jiang; Liu, Hai-Yang

    2011-06-24

    Investigation of whole plants of Euphorbia fischeriana afforded three new tigliane-diterpenoid glycosides, fischerosides A-C (1-3), together with 11 known diterpenoids. Fischerosides A-C (1-3) are the first tigliane-type diterpenoid glucosides. Their structures were determined by a combination of 1D and 2D NMR, MS, and acid hydrolysis. Inhibitory activity against HIV-1 was assessed for compounds 1-5. The new compound 3 showed an EC?? value of 0.02 ?M and a therapeutic index (TI) of 17.50, while prostratin (4) and 12-deoxyphorbol-13,20-diacetate (5) showed significantly greater anti-HIV-1 activity. PMID:21534540

  8. A new cyclolignan glycoside from the tubers of Pinellia ternata.

    PubMed

    Wu, Ying-Ying; Huang, Xiao-Xiao; Wu, Jie; Zhou, Le; Li, Dan-Qi; Liu, Qing-Bo; Li, Ling-Zhi; Yan, Xin-Jia; Song, Shao-Jiang

    2015-11-01

    A new 2,7'-type cyclolignan glycoside, cyclolignanyingoside A (1), together with six known compounds (2-7) were isolated from the tubers of Pinellia ternata (Thunb.) Breit. The structure of 1 was elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR-ESI-MS, and CD spectrometry. The cytotoxic, antioxidant and tyrosinase-inhibiting activities of all the isolates were determined. However, all the isolates exhibited no activity on the selected cell lines (Hep-3B, Bcap-37, and MCF-7). In addition, compounds 1-3 and 7 exhibited strong 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, and compounds 2 and 4 showed a moderate mushroom tyrsinase inhibitory activity. PMID:25989151

  9. Uncommon Glycosidases for the Enzymatic Preparation of Glycosides

    PubMed Central

    Trincone, Antonio

    2015-01-01

    Most of the reports in literature dedicated to the use of glycosyl hydrolases for the preparation of glycosides are about gluco- (α- and β-form) and galacto-sidase (β-form), reflecting the high-availability of both anomers of glucosides and of β-galactosides and their wide-ranging applications. Hence, the idea of this review was to analyze the literature focusing on hardly-mentioned natural and engineered glycosyl hydrolases. Their performances in the synthetic mode and natural hydrolytic potential are examined. Both the choice of articles and their discussion are from a biomolecular and a biotechnological perspective of the biocatalytic process, shedding light on new applicative ideas and on the assortment of biomolecular diversity. The hope is to elicit new interest for the development of biocatalysis and to gather attention of biocatalyst practitioners for glycosynthesis. PMID:26404386

  10. Flavonoid glycosides and pharmacological activity of Amphilophium paniculatum

    PubMed Central

    Nassar, Mahmoud I.; Aboutabl, El-Sayed A.; Eskander, Dina M.; Grace, Mary H.; EL-Khrisy, Ezzel-Din A.; Sleem, Amany A.

    2013-01-01

    Background: Nothing is reported on Amphilophium paniculatum (L.) Kunth. This study aimed at investigation of chemical constituents of the leaves of Amphilophium paniculatum, grown in Egypt, in addition to pharmacological evaluation. Materials and Methods: Isolation of a new compound, along with 5 known flavonoids. Pharmacological activities were carried out on different extracts of A. paniculatum leaves. Results: Identification of a new flavone glycoside, acacetin 8-C-?-D- glucopyranosy l-(1?2)-?-L-rhamnopyranoside (1) in addition to 5 known flavonoids. The 70% ethanol crud extract and its successive chloroform, ethyl acetate, and 100% ethanol extracts showed significant anti-inflammatoryactivity,analgesic effect, antipyretic activity, antioxidant activity, and anti-hyperglycemic activity. Determination of the median lethal dose (LD50) revealed that the different extracts were safe. PMID:23598920

  11. Flavonoid Glycosides from the Seeds of Litchi chinensis.

    PubMed

    Xu, Xinya; Xie, Haihui; Hao, Jing; Jiang, Yueming; Wei, Xiaoyi

    2011-02-23

    Seven flavonoid glycosides, including one new (1) and five previously uncharacterized (3-7), were obtained from the seeds of lychee ( Litchi chinensis Sonn. cv. Heiye) by means of repetitive column chromatography and high-performance liquid chromatography (HPLC) preparation. They were identified as litchioside D (1), (-)-pinocembrin 7-O-neohesperidoside (2), (-)-pinocembrin 7-O-rutinoside (3), taxifolin 4'-O-?-d-glucopyranoside (4), kaempferol 7-O-neohesperidoside (5), tamarixetin 3-O-rutinoside (6), and phlorizin (7) on the basis of spectroscopic analysis and comparison of their data to the values reported in the literatures. Among them, compounds 1, 4, and 5 showed in vitro antitumor activity against A549, LAC, Hep-G2, and HeLa cell lines in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay. PMID:21287989

  12. A new phenylethanoid glycoside from Orobanche cernua Loefling.

    PubMed

    Qu, Zheng-Yi; Zhang, Yu-Wei; Zheng, Si-Wen; Yao, Chun-Lin; Jin, Yin-Ping; Zheng, Pei-He; Sun, Cheng-He; Wang, Ying-Ping

    2016-04-01

    A novel phenylethanoid glycoside, 3'-O-methyl isocrenatoside (1), along with two known compounds, methyl caffeate (2) and protocatechuic aldehyde (3), were isolated from the fresh whole plant of Orobanche cernua Loefling. All the isolated compounds (1-3) were elucidated on the basis of spectroscopic analysis including IR, MS and NMR data. The cytotoxic activities of these compounds were evaluated. Results showed that 3'-O-methyl isocrenatoside (1) and methyl caffeate (2) exhibited significant cytotoxicity, with IC50 values of 71.89, 36.97 μg/mL and 32.32, 34.58 μg/mL against the B16F10 murine melanoma and Lewis lung carcinoma cell lines, respectively. PMID:26358786

  13. Three pairs of diastereoisomeric flavanone glycosides from Viscum articulatum.

    PubMed

    Li, Haizhen; Hou, Zhun; Li, Chao; Zhang, Yao; Shen, Tao; Hu, Qingwen; Ren, Dongmei

    2015-04-01

    Phytochemical examination of the leaves and stems of Viscum articulatum resulted in the isolation of three pairs of new flavanone glycosides, 2R/2S-viscarticulide A-C (1a/1b-3a/3b), together with eight known compounds (7-14). Their structures were established by extensive spectroscopic data analyses. The diastereoisomers were separated by HPLC on a chiral phase and the absolute configuration at C-2 was determined by circular dichroism (CD) spectra. The protective effects of compounds 1-3 against H2O2-induced cytotoxicity with EA.hy926 cells were tested. The results showed that compounds 1-3 improved the survival of EA.hy926 cells after H2O2 exposure at the tested concentrations. PMID:25771122

  14. Acylated C-21 steroidal bisdesmosidic glycosides from Caraluma umbellata.

    PubMed

    Qiu, S X; Lin, L Z; Cordell, G A; Ramesh, M; Kumar, B R; Radhakrishna, M; Mohan, G K; Reddy, B M; Rao, Y N; Srinivas, B; Thomas, N S; Rao, A V

    1997-09-01

    From the whole plant of Caraluma umbellata, three new C-21 steroidal glycosides, named as carumbellosides III-V, were isolated and their structures elucidated by extensive spectroscopic experiments, devoid of any derivatisation, as caralumagenin 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-digitalopyranoside-20-O-be ta- D-glucopyranoside, caralumagenin 3-O-beta-D-glucopyranosy(1-->4)- beta-D-digitalopyranoside-20-O-(2-O- benzoyl)-beta-D-glucopyranoside and caralumagenin 3-O-[6-O-benzoyl-beta-D-glucopyranosyl(1-->4)]-beta-D- digitalopyranoside-20-O-(2-O-benzoyl)-beta-D-glucopyranoside. The determination of the absolute configuration of the aglycone as (20 R), the conformations of the sugars and the unambiguous assignments of their NMR spectroscopic signals were achieved by a combination of 2D-NMR techniques. The isolates were devoid of significant cytotoxity in the UIC human cancer cell panel. PMID:9311154

  15. Triterpene glycosides from the leaves of Pittosporum angustifolium.

    TOXLINE Toxicology Bibliographic Information

    Bcker C; Jenett-Siems K; Siems K; Wurster M; Bodtke A; Chamseddin C; Crsemann M; Lindequist U

    2013-10-01

    Phytochemical investigation of the leaves of Pittosporum angustifolium resulted in the isolation and structural elucidation of nine new triterpene saponins, named pittangretosides A-I (1-9), together with a known compound (10). Mainly by NMR and HRESIMS experiments, eight compounds were identified as A1-barrigenol glycosides (1-7, 10), whereas two compounds exhibited an unusual 17,22-seco-backbone of oleanolic acid (8, 9). All compounds were evaluated for their in vitro cytotoxicities against human urinary bladder carcinoma cells (5637). Only compounds with an angeloyl-residue at C-22 of the aglycone (1-4 and 10) showed antiproliferative effects with IC50 values of 4.1, 5.2, 2.1, 17.9, and 2.4 M, respectively.

  16. Triterpene glycosides from the leaves of Pittosporum angustifolium.

    PubMed

    Bcker, Christian; Jenett-Siems, Kristina; Siems, Karsten; Wurster, Martina; Bodtke, Anja; Chamseddin, Chamseddin; Crsemann, Max; Lindequist, Ulrike

    2013-10-01

    Phytochemical investigation of the leaves of Pittosporum angustifolium resulted in the isolation and structural elucidation of nine new triterpene saponins, named pittangretosides A-I (1-9), together with a known compound (10). Mainly by NMR and HRESIMS experiments, eight compounds were identified as A1-barrigenol glycosides (1-7, 10), whereas two compounds exhibited an unusual 17,22-seco-backbone of oleanolic acid (8, 9). All compounds were evaluated for their in vitro cytotoxicities against human urinary bladder carcinoma cells (5637). Only compounds with an angeloyl-residue at C-22 of the aglycone (1-4 and 10) showed antiproliferative effects with IC50 values of 4.1, 5.2, 2.1, 17.9, and 2.4 M, respectively. PMID:24046217

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

    PubMed

    Cali?, Ihsan; Sezgin, Ykselen; Dnmez, Ali A; Redi, 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). PMID:17253848

  18. An unusual novel anti-oxidant dibenzoyl glycoside from Salvinia natans.

    PubMed

    Narasimhulu, M; Ashalatha, K; Laxmi, P Sri; Sarma, A V S; Rao, B Rama; Kishor, P B Kavi; Krupadanam, G L David; Ali, A Zehra; Tiwari, Asok K; Selvam, A Panneer; Venkateswarlu, Y

    2010-09-01

    An unusual novel and significant anti-oxidant 1,2-dibenzoyl glycoside, natansnin (1), has been isolated from Salvinia natans. The structure of 1 was established by the study of NMR and CD spectral data. PMID:19787545

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

    PubMed

    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 ?M 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. PMID:26068600

  20. Enzyme-catalyzed synthesis of heptyl-?-glycosides: effect of water coalescence at high temperature.

    PubMed

    Montiel, Carmina; Bustos-Jaimes, Ismael; Brzana, Eduardo

    2013-09-01

    Alkyl glycosides can be synthesized by glycosidases in organic media with limited amounts of water. These systems, however, limit the solubility of the sugar substrates and decrease reaction yields. Herein we report the enzymatic synthesis of heptyl-?-glycosides in heptanol catalyzed by a hyperthermophilic ?-glycosidase at 90C. Our results indicate that dispersion of water in heptanol changes with time producing coalescence of water at the bottom of the reactor, playing a key role in the reaction yield. Water-soluble substrate, enzyme and products are concentrated in the aqueous phase, according to their partition coefficients, promoting side reactions that inactivate the enzyme. Reaction yield of heptyl-?-glycosides was 35% relative to lactose, at 7% water. The increase in the water phase to 12% diminished the enzyme inactivation and increased the heptyl-?-glycosides yield to 52%. Surface-active compounds, SDS and octyl glucoside, increased water dispersion but were unable to prevent coalescence. PMID:23863873

  1. Characterization and Modeling of the Collision Induced Dissociation Patterns of Deprotonated Glycosphingolipids: Cleavage of the Glycosidic Bond

    NASA Astrophysics Data System (ADS)

    Rožman, Marko

    2016-01-01

    Glycosphingolipid fragmentation behavior was investigated by combining results from analysis of a series of negative ion tandem mass spectra and molecular modeling. Fragmentation patterns extracted from 75 tandem mass spectra of mainly acidic glycosphingolipid species (gangliosides) suggest prominent cleavage of the glycosidic bonds with retention of the glycosidic oxygen atom by the species formed from the reducing end (B and Y ion formation). Dominant product ions arise from dissociation of sialic acids glycosidic bonds whereas product ions resulting from cleavage of other glycosidic bonds are less abundant. Potential energy surfaces and unimolecular reaction rates of several low-energy fragmentation pathways leading to cleavage of glycosidic bonds were estimated in order to explain observed dissociation patterns. Glycosidic bond cleavage in both neutral (unsubstituted glycosyl group) and acidic glycosphingolipids was the outcome of the charge-directed intramolecular nucleophilic substitution (SN2) mechanism. According to the suggested mechanism, the nucleophile in a form of carboxylate or oxyanion attacks the carbon at position one of the sugar ring, simultaneously breaking the glycosidic bond and yielding an epoxide. For gangliosides, unimolecular reaction rates suggest that dominant product ions related to the cleavage of sialic acid glycosidic bonds are formed via direct dissociation channels. On the other hand, low abundant product ions related to the dissociation of other glycosidic bonds are more likely to be the result of sequential dissociation. Although results from this study mainly contribute to the understanding of glycosphingolipid fragmentation chemistry, some mechanistic findings regarding cleavage of the glycosidic bond may be applicable to other glycoconjugates.

  2. Characterization and Modeling of the Collision Induced Dissociation Patterns of Deprotonated Glycosphingolipids: Cleavage of the Glycosidic Bond

    NASA Astrophysics Data System (ADS)

    Roman, Marko

    2015-08-01

    Glycosphingolipid fragmentation behavior was investigated by combining results from analysis of a series of negative ion tandem mass spectra and molecular modeling. Fragmentation patterns extracted from 75 tandem mass spectra of mainly acidic glycosphingolipid species (gangliosides) suggest prominent cleavage of the glycosidic bonds with retention of the glycosidic oxygen atom by the species formed from the reducing end (B and Y ion formation). Dominant product ions arise from dissociation of sialic acids glycosidic bonds whereas product ions resulting from cleavage of other glycosidic bonds are less abundant. Potential energy surfaces and unimolecular reaction rates of several low-energy fragmentation pathways leading to cleavage of glycosidic bonds were estimated in order to explain observed dissociation patterns. Glycosidic bond cleavage in both neutral (unsubstituted glycosyl group) and acidic glycosphingolipids was the outcome of the charge-directed intramolecular nucleophilic substitution (SN2) mechanism. According to the suggested mechanism, the nucleophile in a form of carboxylate or oxyanion attacks the carbon at position one of the sugar ring, simultaneously breaking the glycosidic bond and yielding an epoxide. For gangliosides, unimolecular reaction rates suggest that dominant product ions related to the cleavage of sialic acid glycosidic bonds are formed via direct dissociation channels. On the other hand, low abundant product ions related to the dissociation of other glycosidic bonds are more likely to be the result of sequential dissociation. Although results from this study mainly contribute to the understanding of glycosphingolipid fragmentation chemistry, some mechanistic findings regarding cleavage of the glycosidic bond may be applicable to other glycoconjugates.

  3. Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity.

    PubMed

    Zhang, Liuqiang; Zhu, Tiantian; Qian, Fei; Xu, Jinwen; Dorje, Gaawe; Zhao, Zhili; Guo, Fujiang; Li, Yiming

    2014-10-01

    Scrodentosides A-E (1-5), five new acylated iridoid glycosides, together with 19 known ones, were isolated from the whole plant of Scrophularia dentata Royle ex Benth. The structures of these isolated glycosides were elucidated by spectroscopic methods. Bioassay showed that compounds 7 and 11 had significant inhibitory effect against NF-?B activation with IC50 value of 43.7 ?M and 1.02 ?M respectively. PMID:25016952

  4. Two New Flavonol Glycosides from Polygala sibirica L. var megalopha Fr.

    PubMed

    Huang, Yan-Jie; Zhou, Ling-Yun; Wang, Jun-Min; Li, Qiang; Geng, Yuan-Yuan; Liu, Hai-Yang; Hua, Yan

    2015-01-01

    Two new flavonol glycosides, named polygalin H (1) and polygalin I (2), as well as the known compound polygalin D (3), were isolated from the whole plant of Polygala sibirica L. var megalopha Fr. Their structures were elucidated on the basis of spectroscopic data analysis. These flavonol glycosides exhibited strong inhibitory activities against xanthine oxidase in vitro. Their half-maximal inhibitory concentrations (IC50) were calculated, which were 9.48, 8.31, 16.00 ?M, respectively. PMID:26633343

  5. Quercetin ameliorates liver injury induced with Tripterygium glycosides by reducing oxidative stress and inflammation.

    PubMed

    Wang, Junming; Miao, Mingsan; Zhang, Yueyue; Liu, Ruixin; Li, Xaobing; Cui, Ying; Qu, Lingbo

    2015-06-01

    Quercetin (Que) is one of main compounds in Lysimachia christinae Hance (Christina loosestrife), and has both medicinal and nutritional value. Glycosides from Tripterygium wilfordii Hook.f. (léi gōng téng [the thunder duke vine]; TG) have diverse and broad bioactivities but with a high incidence of liver injury. Our previous study reported on the hepatoprotective properties of an ethanol extract from L. christinae against TG-induced liver injury in mice. This research is designed to observe, for the first time, the possible protective properties of the compound Que against TG-induced liver injury, and the underlying mechanisms that are involved in oxidative stress and anti-inflammation. The results indicated that TG caused excessive elevation in serum levels of alanine/aspartate transaminase (ALT/AST), alkaline phosphatase (ALP), gamma glutamyl transferase (γ-GT), and pro-inflammatory cytokine tumor necrosis factor-alpha (TNF-α), as well as hepatic lipid peroxidation (all P < 0.01). On the other hand, following TG exposure, we observed significantly reduced levels of biomarkers, including hepatic glutathione (GSH), glutathione-S-transferase (GST), glutathione peroxidase (GPx), and the anti-inflammatory cytokine interleukin (IL)-10, as well as the enzyme activity and mRNA expression of copper- and zinc-containing superoxide dismutase (CuZn-SOD) and catalase (CAT) (all P < 0.01). Nevertheless, all of these alterations were reversed by the pre-administration of Que or the drug bifendate (positive control) for 7 consecutive days. Therefore, this study suggests that Que ameliorates TG-induced acute liver injury, probably through its ability to reduce oxidative stress and its anti-inflammatory properties. PMID:25894526

  6. Arrhythmogenic adverse effects of cardiac glycosides are mediated by redox modification of ryanodine receptors

    PubMed Central

    Ho, Hsiang-Ting; Stevens, Sarah C W; Terentyeva, Radmila; Carnes, Cynthia A; Terentyev, Dmitry; Gyrke, Sandor

    2011-01-01

    Abstract The therapeutic use of cardiac glycosides (CGs), agents commonly used in treating heart failure (HF), is limited by arrhythmic toxicity. The adverse effects of CGs have been attributed to excessive accumulation of intracellular Ca2+ resulting from inhibition of Na+/K+-ATPase ion transport activity. However, CGs are also known to increase intracellular reactive oxygen species (ROS), which could contribute to arrhythmogenesis through redox modification of cardiac ryanodine receptors (RyR2s). Here we sought to determine whether modification of RyR2s by ROS contributes to CG-dependent arrhythmogenesis and examine the relevant sources of ROS. In isolated rat ventricular myocytes, the CG digitoxin (DGT) increased the incidence of arrhythmogenic spontaneous Ca2+ waves, decreased the sarcoplasmic reticulum (SR) Ca2+ load, and increased both ROS and RyR2 thiol oxidation. Additionally, pretreatment with DGT increased spark frequency in permeabilized myocytes. These effects on Ca2+ waves and sparks were prevented by the antioxidant N-(2-mercaptopropionyl) glycine (MPG). The CG-dependent increases in ROS, RyR2 oxidation and arrhythmogenic propensity were reversed by inhibitors of NADPH oxidase, mitochondrial ATP-dependent K+ channels (mito-KATP) or permeability transition pore (PTP), but not by inhibition of xanthine oxidase. These results suggest that the arrhythmogenic adverse effects of CGs involve alterations in RyR2 function caused by oxidative changes in the channel structure by ROS. These CG-dependent effects probably involve release of ROS from mitochondria possibly mediated by NADPH oxidase. PMID:21807619

  7. Taming the Reactivity of Glycosyl Iodides To Achieve Stereoselective Glycosidation.

    PubMed

    Gervay-Hague, Jacquelyn

    2016-01-19

    Although glycosyl iodides have been known for more than 100 years, it was not until the 21st century that their full potential began to be harnessed for complex glycoconjugate synthesis. Mechanistic studies in the late 1990s probed glycosyl iodide formation by NMR spectroscopy and revealed important reactivity features embedded in protecting-group stereoelectronics. Differentially protected sugars having an anomeric acetate were reacted with trimethylsilyl iodide (TMSI) to generate the glycosyl iodides. In the absence of C-2 participation, generation of the glycosyl iodide proceeded by inversion of the starting anomeric acetate stereochemistry. Once formed, the glycosyl iodide readily underwent in situ anomerization, and in the presence of excess iodide, equilibrium concentrations of α- and β-iodides were established. Reactivity profiles depended upon the identity of the sugar and the protecting groups adorning it. Consistent with the modern idea of disarmed versus armed sugars, ester protecting groups diminished the reactivity of glycosyl iodides and ether protecting groups enhanced the reactivity. Thus, acetylated sugars were slower to form the iodide and anomerize than their benzylated analogues, and these disarmed glycosyl iodides could be isolated and purified, whereas armed ether-protected iodides could only be generated and reacted in situ. All other things being equal, the β-iodide was orders of magnitude more reactive than the thermodynamically more stable α-iodide, consistent with the idea of in situ anomerization introduced by Lemieux in the mid-20th century. Glycosyl iodides are far more reactive than the corresponding bromides, and with the increased reactivity comes increased stereocontrol, particularly when forming α-linked linear and branched oligosaccharides. Reactions with per-O-silylated glycosyl iodides are especially useful for the synthesis of α-linked glycoconjugates. Silyl ether protecting groups make the glycosyl iodide so reactive that even highly functionalized aglycon acceptors add. Following the coupling event, the TMS ethers are readily removed by methanolysis, and since all of the byproducts are volatile, multiple reactions can be performed in a single reaction vessel without isolation of intermediates. In this fashion, per-O-TMS monosaccharides can be converted to biologically relevant α-linked glycolipids in one pot. The stereochemical outcome of these reactions can also be switched to β-glycoside formation by addition of silver to chelate the iodide, thus favoring SN2 displacement of the α-iodide. While iodides derived from benzyl and silyl ether-protected oligosaccharides are susceptible to interglycosidic bond cleavage when treated with TMSI, the introduction of a single acetate protecting group prevents this unwanted side reaction. Partial acetylation of armed glycosyl iodides also attenuates HI elimination side reactions. Conversely, fully acetylated glycosyl iodides are deactivated and require metal catalysis in order for glycosidation to occur. Recent findings indicate that I2 activation of per-O-acetylated mono-, di-, and trisaccharides promotes glycosidation of cyclic ethers to give β-linked iodoalkyl glycoconjugates in one step. Products of these reactions have been converted into multivalent carbohydrate displays. With these synthetic pathways elucidated, chemical reactivity can be exquisitely controlled by the judicious selection of protecting groups to achieve high stereocontrol in step-economical processes. PMID:26524481

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

    PubMed

    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: 38.79μg CGG per ml and 50.57μg phenolics per ml; cherry liqueur 16.08μg CGG per ml and 27.73μg 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. PMID:26948641

  9. Influence of steviol glycosides on the stability of vitamin C and anthocyanins.

    PubMed

    Wo?niak, ?ukasz; Marsza?ek, Krystian; Sk?pska, Sylwia

    2014-11-19

    A high level of sweetness and health-promoting properties make steviol glycosides an interesting alternative to sugars or artificial sweeteners. The radical oxygen species scavenging activity of these compounds may influence the stability of labile particles present in food. Model buffer solutions containing steviol glycosides, a selected food antioxidant (vitamin C or anthocyanins), and preservative were analyzed during storage. The addition of steviol glycosides at concentrations of 50, 125, and 200 mg/L increased the stability of both ascorbic and dehydroascorbic acid (degradation rates decreased up to 3.4- and 4.5-fold, respectively); the effect was intensified by higher sweetener concentrations and higher acidity of the solutions. Glycosides used alone did not affect the stability of anthocyanins; however, they enhanced the protective effect of sugars; half-life times increased by ca. 33% in the presence of sucrose (100 g/L) and by ca. 52% when both sucrose (100 g/L) and glycosides (total 200 mg/L) were used. Steviol glycosides concentrations remained stable during experiments. PMID:25376304

  10. Fecalase: a model for activation of dietary glycosides to mutagens by intestinal flora.

    PubMed Central

    Tamura, G; Gold, C; Ferro-Luzzi, A; Ames, B N

    1980-01-01

    Many substances in the plant kingdom and in man's diet occur as glycosides. Recent studies have indicated that many glycosides that are not mutagenic in tests such as the Salmonella test become mutagenic upon hydrolysis of the glycosidic linkages. The Salmonella test utilizes a liver homogenate to approximate mammalian metabolism but does not provide a source of the enzymes present in intestinal bacterial flora that hydrolyze the wide variety of glycosides present in nature. We describe a stable cell-free extract of human feces, fecalase, which is shown to contain various glycosidases that allow the in vitro activation of many natural glycosides to mutagens in the Salmonella/liver homogenate test. Many beverages, such as red wine (but apparently not white wine) and tea, contain glycosides of the mutagne quercetin. Red wine, red grape juice, and tea were mutagenic in the test when fecalase was added, and red wine contained considerable direct mutagenic activity in the absence of fecalase. The implications of quercetin mutagenicity and carcinogenicity are discussed. PMID:6933540

  11. Fecalase: a model for activation of dietary glycosides to mutagens by intestinal flora

    SciTech Connect

    Tamura, G.; Gold, C.; Ferro-Luzzi, A.; Ames, B.N.

    1980-08-01

    Many substances in the plant kingdom and in man's diet occur as glycosides. Recent studies have indicated that many glycosides that are not mutagenic in tests such as the Salmonella test become mutagenic upon hydrolysis of the glycosidic linkages. The Salmonella test utilizes a liver homogenate to approximate mammalian metabolism but does not provide a source of the enzymes present in intestinal bacterial flora that hydrolyze the wide variety of glycosides present in nature. We describe a stable cell-free extract of human feces, fecalase, which is shown to contain various glycosidases that allow the in vitro activation of many natural glycosides to mutagens in the Salmonella/liver homogenate test. Many beverages, such as red wine (but apparently not white wine) and tea, contain glycosides of the mutagen quercetin. Red wine, red grape juice, and teas were mutagenic in the test when fecalase was added, and red wine contained considerable direct mutagenic activity in the absence of fecalase. The implications of quercetin mutagenicity and carcinogenicity are discussed.

  12. Oleanolic acid and hederagenin glycosides from Weigela stelzneri.

    PubMed

    Rezgui, Abdelmalek; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Delemasure, Stphanie; Dutartre, Patrick; Lacaille-Dubois, Marie-Aleth

    2016-03-01

    Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-?-d-glucopyranosyl-(1?2)-[?-d-xylopyranosyl-(1?4)]-?-d-xylopyranosyl-(1?4)-?-d-xylopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-l-arabinopyranosyloleanolic acid, 3-O-?-d-glucopyranosyl-(1?2)-[?-d-xylopyranosyl-(1?4)]-?-d-xylopyranosyl-(1?4)-?-d-xylopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-d-xylopyranosyloleanolic acid, 3-O-?-d-glucopyranosyl-(1?2)-[?-d-glucopyranosyl-(1?4)]-?-d-xylopyranosyl-(1?4)-?-d-xylopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-d-xylopyranosyloleanolic acid, 3-O-?-d-glucopyranosyl-(1?2)-[?-d-xylopyranosyl-(1?4)]-?-d-xylopyranosyl-(1?4)-?-d-xylopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-l-arabinopyranosyloleanolic acid 28-O-?-d-glucopyranosyl-(1?6)-?-d-glucopyranosyl ester, and 3-O-?-d-glucopyranosyl-(1?2)-?-l-arabinopyranosylhederagenin 28-O-?-d-xylopyranosyl-(1?6)-[?-l-rhamnopyranosyl-(1?2)]-?-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-?-d-glucopyranosyl-(1?2)-[?-d-xylopyranosyl-(1?4)]-?-d-xylopyranosyl-(1?4)-?-d-xylopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-l-arabinopyranosyloleanolic acid and 3-O-?-d-glucopyranosyl-(1?2)-[?-d-xylopyranosyl-(1?4)]-?-d-xylopyranosyl-(1?4)-?-d-xylopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1? production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively. PMID:26805449

  13. Reversible inhibitors of beta-glucosidase.

    PubMed

    Dale, M P; Ensley, H E; Kern, K; Sastry, K A; Byers, L D

    1985-07-01

    A variety of reversible inhibitors of sweet almond beta-glucosidase were examined. These included simple sugars and sugar derivatives, amines and phenols. With respect to the sugar inhibitors and, indeed, the various glycoside substrates, the enzyme has what can be considered a "relaxed specificity". No single substituent on glucose, for example, is essential for binding. Replacement of a hydroxyl group with an anionic substituent reduces the affinity while substitution with a cationic (amine) substituent enhances the affinity. Amines, in general, are good inhibitors, binding more tightly than the corresponding alcohols: pKiRNH3+ = 0.645pKiROH + 1.77 (n = 9, r = 0.97). The affinity of a series of 10 primary amines was found to be strongly influenced by substituent hydrophobicity: pKi = 0.52 pi + 1.32 (r = 0.95). The major binding determinant of the glycoside substrates is the aglycon moiety. Thus, the Ki values of phenols are similar in magnitude to the Ks values of the corresponding aryl beta-glucoside. The pH dependence for the inhibition by various phenols indicates that it is the un-ionized phenol which binds to the enzyme when an enzymic group of pKa = 6.8 (+/- 0.1) is protonated. The affinity of the phenol inhibitor is dependent on its basicity with a Brnsted coefficient for binding of beta = -0.26 (n = 14, r = 0.98). The pH dependence of the binding of two particularly potent beta-glucosidase inhibitors was also examined. 1-Deoxynojirimycin (1,5-dideoxy-1,5-imino-D-glucitol) has a pH-corrected Ki = 6.5 microM, and D-glucono-1,5-lactam has a pH-corrected Ki = 29 microM.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:3929833

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

    PubMed

    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 2-516?g/mL. And compound 29 showed the highest antibacterial activity against S. aureus ATCC 29213 with MIC values of 2?g/mL, while the MIC values of levofloxacin was 8?g/mL. Three compounds (29, 33, 36) exhibited antibacterial activities against S. aureus ATCC 25923 with MIC values of 256-516?g/mL. Two compounds (29, 33) exhibited antibacterial activities against A. baumanii ATCC 19606 with MIC values of 128-516?g/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. PMID:25598187

  15. Extracellular Glycoside Hydrolase Activities in the Human Oral Cavity

    PubMed Central

    Walker, Lauren C.; Dodds, Michael W. J.; Hanley, A. Bryan

    2015-01-01

    Carbohydrate availability shifts when bacteria attach to a surface and form biofilm. When salivary planktonic bacteria form an oral biofilm, a variety of polysaccharides and glycoproteins are the primary carbon sources; however, simple sugar availabilities are limited due to low diffusion from saliva to biofilm. We hypothesized that bacterial glycoside hydrolase (GH) activities would be higher in a biofilm than in saliva in order to maintain metabolism in a low-sugar, high-glycoprotein environment. Salivary bacteria from 13 healthy individuals were used to grow in vitro biofilm using two separate media, one with sucrose and the other limiting carbon sources to a complex carbohydrate. All six GHs measured were higher in vitro when grown in the medium with complex carbohydrate as the sole carbon source. We then collected saliva and overnight dental plaque samples from the same individuals and measured ex vivo activities for the same six enzymes to determine how oral microbial utilization of glycoconjugates shifts between the planktonic phase in saliva and the biofilm phase in overnight dental plaque. Overall higher GH activities were observed in plaque samples, in agreement with in vitro observation. A similar pattern was observed in GH activity profiles between in vitro and ex vivo data. 16S rRNA gene analysis showed that plaque samples had a higher abundance of microorganisms with larger number of GH gene sequences. These results suggest differences in sugar catabolism between the oral bacteria located in the biofilm and those in saliva. PMID:26048943

  16. Effects of synthetic glycosides on steroid balance in Macaca fascicularis

    SciTech Connect

    Malinow, M.R.; Elliott, W.H.; McLaughlin, P.; Upson, B.

    1987-01-01

    The predominantly beta-anomer of diosgenin glucoside (DG) was synthesized and its effects on cholesterol homeostasis were tested in monkeys. Cynomolgus macaques (Macaca fascicularis) were fed, during two 3-week periods, a semipurified diet with 0.1% cholesterol and a similar ration containing 1% DG, respectively. A Chow diet was given for 5 weeks between the experimental periods. Cholesterol and bile acid balance were analyzed during the last week of each semipurified diet. Diosgenin glucoside reduced cholesterolemia from 292 mg/dl to 172 mg/dl, decreased intestinal absorption of exogenous cholesterol from 62.4% to 26.0%, and increased secretion of endogenous cholesterol from -0.8 to 93.5 mg/day. The fecal excretion of neutral steroids rose from 40.7 to 157.3 mg/day; that of bile acids changed, nonsignificantly, from 23.1 to 16.0 mg/day. The cholesterol balance was -44 mg/day in the control period, and 88 mg/day in the DG-fed animals. No toxic signs were observed. Thus, when long-term studies demonstrate that the glucoside is well tolerated, DG and other synthetic glycosides with similar activities may be of use in the management of hypercholesterolemia and atherosclerosis.

  17. Polyketide Glycosides from Bionectria ochroleuca Inhibit Candida albicans Biofilm Formation

    PubMed Central

    2015-01-01

    One of the challenges presented by Candida infections is that many of the isolates encountered in the clinic produce biofilms, which can decrease these pathogens susceptibilities to standard-of-care antibiotic therapies. Inhibitors of fungal biofilm formation offer a potential solution to counteracting some of the problems associated with Candida infections. A screening campaign utilizing samples from our fungal extract library revealed that a Bionectria ochroleuca isolate cultured on Cheerios breakfast cereal produced metabolites that blocked the in vitro formation of Candida albicans biofilms. A scale-up culture of the fungus was undertaken using mycobags (also known as mushroom bags or spawn bags), which afforded four known [TMC-151s CF (14)] and three new [bionectriols BD (57)] polyketide glycosides. All seven metabolites exhibited potent biofilm inhibition against C. albicans SC5314, as well as exerted synergistic antifungal activities in combination with amphotericin B. In this report, we describe the structure determination of the new metabolites, as well as compare the secondary metabolome profiles of fungi grown in flasks and mycobags. These studies demonstrate that mycobags offer a useful alternative to flask-based cultures for the preparative production of fungal secondary metabolites. PMID:25302529

  18. Polyketide glycosides from Bionectria ochroleuca inhibit Candida albicans biofilm formation.

    PubMed

    Wang, Bin; You, Jianlan; King, Jarrod B; Cai, Shengxin; Park, Elizabeth; Powell, Douglas R; Cichewicz, Robert H

    2014-10-24

    One of the challenges presented by Candida infections is that many of the isolates encountered in the clinic produce biofilms, which can decrease these pathogens' susceptibilities to standard-of-care antibiotic therapies. Inhibitors of fungal biofilm formation offer a potential solution to counteracting some of the problems associated with Candida infections. A screening campaign utilizing samples from our fungal extract library revealed that a Bionectria ochroleuca isolate cultured on Cheerios breakfast cereal produced metabolites that blocked the in vitro formation of Candida albicans biofilms. A scale-up culture of the fungus was undertaken using mycobags (also known as mushroom bags or spawn bags), which afforded four known [TMC-151s C-F (1-4)] and three new [bionectriols B-D (5-7)] polyketide glycosides. All seven metabolites exhibited potent biofilm inhibition against C. albicans SC5314, as well as exerted synergistic antifungal activities in combination with amphotericin B. In this report, we describe the structure determination of the new metabolites, as well as compare the secondary metabolome profiles of fungi grown in flasks and mycobags. These studies demonstrate that mycobags offer a useful alternative to flask-based cultures for the preparative production of fungal secondary metabolites. PMID:25302529

  19. beta-glucosidase catalyzed syntheses of pyridoxine glycosides.

    PubMed

    Charles, Rajachristu Einstein; Divakar, Soundar

    2009-01-01

    Enzymatic syntheses of pyridoxine glycosides were carried out in di-isopropyl ether organic medium using beta-glucosidase isolated from sweet almond. Optimum conditions determined for the reaction with D-glucose were 40% (w/w D-glucose) beta-glucosidase at 0.18 mM (1.8 ml) of pH 5 acetate buffer over a 72 h incubation period. Of 11 carbohydrates employed, beta-glucosidase gave 7-O-(alpha-D-glucopyranosyl)pyridoxine 5a, 7-O-(beta-D-glucopyranosyl)pyridoxine 5b, 6-O-(alpha-D-glucopyranosyl)pyridoxine 5c, 7-O-(alpha-D-galactopyranosyl)pyridoxine 6a, 7-O-(beta-D-galactopyranosyl)pyridoxine 6b, 6-O-(alpha-D-galactopyranosyl)pyridoxine 6c, 7-O-(alpha-D-mannopyranosyl)pyridoxine 7a, 7-O-(beta-D-mannopyranosyl)pyridoxine 7b, and 6-O-(alpha-D-mannopyranosyl)pyridoxine 7c in yields ranging from 23 to 40%. PMID:19129657

  20. Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria.

    PubMed

    Cioffi, Giuseppina; Morales Escobar, Luis; Braca, Alessandra; De Tommasi, Nunziatina

    2003-08-01

    Four chalcone glycosides (1-4), including three new natural products, and three flavanones (5-7) were isolated from the methanol extract of stem bark of Maclura tinctoria. The new compounds have been characterized as 4'-O-beta-D-(2' '-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone (1), 4'-O-beta-D-(2' '-p-coumaroyl-6' '-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone (2), and 3'-(3-methyl-2-butenyl)-4'-O-beta-D-glucopyranosyl-4,2'-dihydroxychalcone (3); the known derivatives were elucidated as 4'-O-beta-D-(2' '-acetyl-6' '-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone (4), eriodictyol 7-O-beta-D-glucopyranoside (5), naringenin (6), and naringenin 4'-O-beta-D-glucopyranoside (7). Their structures were determined by 1D and 2D NMR and ESIMS. The antioxidant activity of all the isolated compounds was determined by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equivalent Antioxidant Capacity (TEAC) assay and the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay). The results showed that compound 3 was the most active in both antioxidant assays. PMID:12932124

  1. Steroidal glycosides from the marine sponge Pandaros acanthifolium.

    PubMed

    Cachet, Nadja; Regalado, Erik L; Genta-Jouve, Grgory; Mehiri, Mohamed; Amade, Philippe; Thomas, Olivier P

    2009-09-01

    The chemical composition of the Caribbean sponge Pandaros acanthifolium was investigated and led to the isolation of seven new steroidal glycosides namely pandarosides A-D (1, 3, 4 and 6) along with the three methyl esters of pandarosides A, C, and D (2, 5 and 7). Their structures were characterized as 3beta-[beta-glucopyranosyl-(1-->2)-beta-glucopyranosyloxyuronic acid]-16-hydroxy-5alpha,14beta-poriferast-16-ene-15,23-dione (1) and its methyl ester (2), 3beta-[beta-glucopyranosyloxyuronic acid]-16-hydroxy-5alpha,14beta-poriferast-16-ene-15,23-dione (3), 3beta-[beta-glucopyranosyl-(1-->2)-beta-glucopyranosyloxyuronic acid]-16-hydroxy-5alpha,14beta-cholest-16-ene-15,23-dione (4) and its methyl ester (5), 3beta-(beta-glucopyranosyloxyuronic acid)-16-hydroxy-5alpha,14beta-cholest-16-ene-15,23-dione (6) and its methyl ester (7) on the basis of detailed spectroscopic analyses, including 2D NMR and HRESIMS studies. Pandarosides A-D and their methyl esters (1-7) are all characterized by a rare 2-hydroxycyclopentenone D-ring with a 14beta configuration. The absolute configuration of the aglycon part of pandaroside A (1) was assigned by comparison between experimental and TDDFT calculated circular dichroism spectra on the more stable conformer. PMID:19541002

  2. Antioxidative iridoid glycosides from the sky flower (Duranta repens Linn).

    PubMed

    Ijaz, Fozia; Ul Haq, Azhar; Ahmad, Ijaz; Ahmad, Nisar; Hussain, Javid; Chen, Sibao

    2011-02-01

    Phytochemical investigations were performed on the EtOAc-soluble fraction of the whole plant of the sky flower (Duranta repens) which led to the isolation of the iridoid glycosides 1-6. Their structures were elucidated by both 1D and 2D NMR spectroscopic analysis. All the compounds showed potent antioxidative scavenging activity in four different tests, with half maximal inhibitory concentration (IC(50)) values in the range 0.481-0.719 mM against DPPH radicals, 4.07-17.21 μM for the hydroxyl radical (·OH) inhibitory activity test, 43.3-97.37 μM in the total reactive oxygen species (ROS) inhibitory activity test, and 3.39-18.94 μM in the peroxynitrite (ONOO(-)) scavenging activity test. Duranterectoside A (1) displayed the strongest scavenging potential with IC(50) values of (0.481 ± 0.06 mM, 4.07 ± 0.03, 43.30 ± 0.05, 3.39 ± 0.02 μM) for the DPPH radicals, ·OH inhibitory activity test, total ROS inhibitory activity test and the ONOO(-) scavenging activity test, respectively. PMID:21299433

  3. Host dependent iridoid glycoside sequestration patterns in Cionus hortulanus.

    PubMed

    Baden, Christian Ulrich; Franke, Stephan; Dobler, Susanne

    2013-08-01

    Weevils of the genus Cionus (Curculionidae, Mecininae) sequester the iridoid glycosides (IGs) aucubin and catalpol from their host plants Scrophularia or Verbascum (Scrophulariaceae). Cionus hortulanus is the only member of the genus that feeds on both plant genera. We previously showed that sequestration patterns in C. hortulanus depend on the local host. To investigate whether IG patterns are driven by their availability in the hosts or genetic differences between populations, we collected C. hortulanus from S. nodosa in the field and reared them either on S. nodosa or on V. nigrum. The differences in IG concentrations were specific for the host plant upon which the weevils developed. Similar to monophagous species of the Cionini, individuals from S. nodosa had more aucubin than catalpol and mirrored the concentrations of their host plants. Specimens from V. nigrum, on the other hand, had higher concentrations of aucubin and of catalpol than their host. On V. nigrum, the ratio of catalpol to aucubin differed significantly between plant and beetle samples due to much higher catalpol concentrations in the weevils. Our data thus contradict genetically fixed differences between populations living on either plant but rather document the host plants' influence on the beetles' metabolism. PMID:23846185

  4. FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs.

    PubMed

    Marzag, Hamid; Robert, Guillaume; Dufies, Maeva; Bougrin, Khalid; Auberger, Patrick; Benhida, Rachid

    2015-01-01

    Phenol derived O-glycosides were synthesized using a direct and convenient O-glycosidation, starting from acetylated sugars in the presence of FeCl3, an inexpensive, mild and benign Lewis acid catalyst. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions leading to the corresponding ?-O-glycosides as the major anomer. Post-synthetic transformations of iodophenol intermediates led to new resveratrol O-glycoside analogs in good overall yields. PMID:24961448

  5. Syntheses of N-vanillyl-nonanamide glycosides using amyloglucosidase from Rhizopus and beta-glucosidase from sweet almond.

    PubMed

    Sivakumar, Ramaiah; Divakar, Soundar

    2007-10-01

    Enzymatic syntheses of N-vanillyl-nonanamide, 1, glycosides with D-glucose, 2, D-galactose, 3, D-mannose, 4, D-ribose, 5, maltose, 6, and lactose, 7, were carried out using amyloglucosidase from Rhizopus and beta-glucosidase from sweet almond. The latter catalysed the syntheses of N-vanillyl-nonanamide glycosides (8-13) and exclusively yielded beta-glycosides with carbohydrates 2, 3, 4, 6 and 7, while amyloglucosidase yielded C1-alpha- and beta-glycosides and 6-O-aryl derivatives (8, 9, 11 and 12). PMID:17609862

  6. A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species.

    PubMed

    Pičmanová, Martina; Neilson, Elizabeth H; Motawia, Mohammed S; Olsen, Carl Erik; Agerbirk, Niels; Gray, Christopher J; Flitsch, Sabine; Meier, Sebastian; Silvestro, Daniele; Jørgensen, Kirsten; Sánchez-Pérez, Raquel; Møller, Birger Lindberg; Bjarnholt, Nanna

    2015-08-01

    Cyanogenic glycosides are phytoanticipins involved in plant defence against herbivores by virtue of their ability to release toxic hydrogen cyanide (HCN) upon tissue disruption. In addition, endogenous turnover of cyanogenic glycosides without the liberation of HCN may offer plants an important source of reduced nitrogen at specific developmental stages. To investigate the presence of putative turnover products of cyanogenic glycosides, comparative metabolic profiling using LC-MS/MS and high resolution MS (HR-MS) complemented by ion-mobility MS was carried out in three cyanogenic plant species: cassava, almond and sorghum. In total, the endogenous formation of 36 different chemical structures related to the cyanogenic glucosides linamarin, lotaustralin, prunasin, amygdalin and dhurrin was discovered, including di- and tri-glycosides derived from these compounds. The relative abundance of the compounds was assessed in different tissues and developmental stages. Based on results common to the three phylogenetically unrelated species, a potential recycling endogenous turnover pathway for cyanogenic glycosides is described in which reduced nitrogen and carbon are recovered for primary metabolism without the liberation of free HCN. Glycosides of amides, carboxylic acids and 'anitriles' derived from cyanogenic glycosides appear as common intermediates in this pathway and may also have individual functions in the plant. The recycling of cyanogenic glycosides and the biological significance of the presence of the turnover products in cyanogenic plants open entirely new insights into the multiplicity of biological roles cyanogenic glycosides may play in plants. PMID:26205491

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

    PubMed Central

    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 < 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. PMID:25993258

  8. Antioxidant and Anti-Inflammatory Phenolic Glycosides from Clematis tashiroi.

    PubMed

    Zhang, Li-Jie; Huang, Hung-Tse; Huang, Shih-Yen; Lin, Zhi-Hu; Shen, Chien-Chang; Tsai, Wei-Jern; Kuo, Yao-Haur

    2015-07-24

    From the 95% EtOH extract of dried aerial parts of Clematis tashiroi, eight new and four known phenolic (caffeic acid, coumaric acid, ferrulic acid) glycosides were isolated and characterized. The structures of the new isolates (clematisides A-H) were elucidated by spectroscopic data interpretation as trans-4-O-(6-O-trans-caffeoyl-β-D- glucopyranosyl)-9-O-β-D-glucopyranosyl caffeic acid (1), trans-4-O-(6-O-trans-feruloyl-β-D-glucopyranosyll)-9-O-β-D-glucopyranosyl caffeic acid (2), trans-4-O-(6-O-trans-p-coumaroyl-β-D-glucopyranosyl)-9-O-β-D-glucopyranosyl caffeic acid (3), trans-4-O-(6-O-trans-caffeoyl-β-D-glucopyranosyl)-9-O-β-D-glucopyranosyl p-coumaric acid (4), trans-3-O-(6-O-trans-caffeoyl-β-D-glucopyranosyl)-9-O-β-D-glucopyranosyl caffeic acid (5), trans-3-O-(6-O-trans-p-coumaroyl-β-D-glucopyranosyl)-9-O-β-D-glucopyranosyl caffeic acid (6), 6-(3',4'-dihydroxystyryl)-2-pyrone-4-O-(6-O-trans-caffeoyl)-β-D-glucopyranoside (7), and 6-(3',4'-dihydroxystyryl)-2-pyrone-4-O-{6-O-[4-O-(6-O-trans-caffeoyl)-β-D-glucopyranosyl]-trans-caffeoyl}-β-D-glucopyranoside (8), respectively. In a DPPH radical-scavenging test, compounds 1, 7, and 8 showed more potent antioxidant activity than that of the positive control, vitamin E. In addition, compound 7 also showed inhibitory activity in an antinitric oxide release assay. PMID:26143931

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

    SciTech Connect

    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.

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

    PubMed Central

    2011-01-01

    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-?-L-arabinofuranoside, one enzyme had significant activity against p-nitrophenyl-?-D-glucopyranoside, and one enzyme showed significant activity against p-nitrophenyl-?-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. PMID:21816041

  11. Reversible Thermoset Adhesives

    NASA Technical Reports Server (NTRS)

    Mac Murray, Benjamin C. (Inventor); Tong, Tat H. (Inventor); Hreha, Richard D. (Inventor)

    2016-01-01

    Embodiments of a reversible thermoset adhesive formed by incorporating thermally-reversible cross-linking units and a method for making the reversible thermoset adhesive are provided. One approach to formulating reversible thermoset adhesives includes incorporating dienes, such as furans, and dienophiles, such as maleimides, into a polymer network as reversible covalent cross-links using Diels Alder cross-link formation between the diene and dienophile. The chemical components may be selected based on their compatibility with adhesive chemistry as well as their ability to undergo controlled, reversible cross-linking chemistry.

  12. Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armeddisarmed strategy

    PubMed Central

    Kayastha, Abhijeet K

    2013-01-01

    Summary 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. PMID:24204427

  13. Cardiac Glycosides Induce Cell Death in Human Cells by Inhibiting General Protein Synthesis

    PubMed Central

    Steinrueck, Magdalena; Craig-Mueller, Nils; Mayerhofer, Julia; Schwarzinger, Ilse; Sloane, Mathew; Uras, Iris Z.; Hoermann, Gregor; Nijman, Sebastian M. B.; Mayerhofer, Matthias

    2009-01-01

    Background Cardiac glycosides are Na+/K+-pump inhibitors widely used to treat heart failure. They are also highly cytotoxic, and studies have suggested specific anti-tumor activity leading to current clinical trials in cancer patients. However, a definitive demonstration of this putative anti-cancer activity and the underlying molecular mechanism has remained elusive. Methodology/Principal Findings Using an unbiased transcriptomics approach, we found that cardiac glycosides inhibit general protein synthesis. Protein synthesis inhibition and cytotoxicity were not specific for cancer cells as they were observed in both primary and cancer cell lines. These effects were dependent on the Na+/K+-pump as they were rescued by expression of a cardiac glycoside-resistant Na+/K+-pump. Unlike human cells, rodent cells are largely resistant to cardiac glycosides in vitro and mice were found to tolerate extremely high levels. Conclusions/Significance The physiological difference between human and mouse explains the previously observed sensitivity of human cancer cells in mouse xenograft experiments. Thus, published mouse xenograft models used to support anti-tumor activity for these drugs require reevaluation. Our finding that cardiac glycosides inhibit protein synthesis provides a mechanism for the cytotoxicity of CGs and raises concerns about ongoing clinical trials to test CGs as anti-cancer agents in humans. PMID:20016840

  14. Factors influencing the variability of antioxidative phenolic glycosides in Salix species.

    PubMed

    Frster, Nadja; Ulrichs, Christian; Zander, Matthias; Ktzel, Ralf; Mewis, Inga

    2010-07-28

    Phenolic glycosides, especially the salicylates, are important secondary metabolites in the bark of willows (Salix spp.). Because of their anti-inflammatory, analgesic, and fever-reducing properties, they are of particular interest to society. Compared to the fabrication of synthetic salicylacetylic acid, the commercial production of willow bark extracts with adequate amounts of salicylate is very difficult due to several biological and technical reasons. Therefore, one of the objectives was to identify salicylate-rich clones from three species, Salix daphnoides , Salix purpurea , and Salix pentandra , with potentially high amounts of phenolic glycosides. Three hundred different Salix clones were collected, and the chemical profiles of their bark were analyzed by HPLC. Overall, S. daphnoides clones showed the highest phenolic glycoside contents, followed by S. purpurea and S. pentandra. Second, seasonal changes of secondary compounds in willow bark were analyzed to determine the optimal harvesting time. The phenolic glycoside levels decreased over the growing season, with highest contents detected during plant dormancy. The effects of different cultivation conditions were also examined, and none of these treatments were found to have a significant effect on the phenolic glycoside content in willow bark. Biomass accumulation in the clones with grass competition was significantly lower than in the other three treatments. PMID:20593762

  15. Glycoside esters of 5-aminolevulinic acid for photodynamic therapy of cancer.

    PubMed

    Vallinayagam, Ramakrishnan; Schmitt, Frdric; Barge, Jrome; Wagnieres, Georges; Wenger, Virginie; Neier, Reinhard; Juillerat-Jeanneret, Lucienne

    2008-04-01

    Aliphatic and ethylene glycol esters of 5-aminolevulinic acid (ALA) are very efficient precursors of the photosensitizer protoporphyrin IX (PpIX) for photodynamic therapy; however, they diffuse passively across the cell membrane and thus lack cell selectivity. We evaluated whether alpha-glucose, alpha-mannose, or beta-galactose esters of ALA would present improved properties as precursors of PpIX. Esterification was performed either at the position O-1 or O-6 of the sugars with or without an ethylene glycol linker, and these glycoside esters of ALA were evaluated in human cells. The results demonstrated that glycoside esters of ALA are efficient precursors of PpIX in human cancer and angiogenic endothelial cells, comparable to free ALA, but not in normal human fibroblasts. PpIX production was confirmed by fluorescence microscopy and photodynamic treatment of cells. The O-1 or O-6 positions of functionalization and the nature of the sugar moiety did not influence PpIX production. The presence of the ethylene glycol linker generally resulted in decreased PpIX production. The uptake of these glycoside esters of ALA by cells was not decreased in the presence of high concentrations of the related sugars. Inhibitors of alpha-glucosidases or alpha-mannosidases did not decrease PpIX production. These results suggest the involvement of active non-glycoside-specific membrane transporter(s) for uptake and of esterases rather than glycosidases in the release of ALA from the glycoside esters of ALA. PMID:18341270

  16. Preparation of vesicle drug carrier from palm oil- and palm kernel oil-based glycosides.

    PubMed

    Aripin, Nurul Fadhilah Kamalul; Park, Jae Won; Park, Hyun Jin

    2012-06-15

    A new mixture of alkyl glycosides derived from palm oil (PO) or palm kernel oil (PKO) was synthesised. This mixture contains glycosylated disaccharide of either maltose or lactose with aliphatic chain that varies according to the PO or PKO fatty acids composition. The synthesis method produced no polymerised sugar unlike the production of the commercial glycosides (APG). The mixture only contains various glycosides differing by the alkyl chain and stereoisomers. Three anomeric mixtures can be produced depending on the reaction time and catalyst: α-dominant mixture, β-dominant mixture and equal mixture. The PO and PKO derived glycosides were able to form a stable vesicle with a small amount of dicetyl phosphate (DCP) and showed high vitamin E encapsulation efficiency. Low packing density of the membrane bilayer enabled more vitamin E to participate in the membrane formation. The anomeric mixtures of the maltosides provide no difference in membrane packing behaviour as it was governed by the hydrophilic region. Significant difference in membrane packing density was observed for lactosides anomeric mixtures because the packing behaviour was influenced by the hydrophobic region. Inclusion of cholesterol led to decrease in vitamin E encapsulation as well as reducing the stability of the vesicle system. The vesicular formulations of the glycosides were stable for 3 months when stored at refrigeration temperature. PMID:22421415

  17. Tubal ligation reversal

    MedlinePLUS

    Tubal ligation reversal is surgery done to allow a woman who has had her tubes tied (tubal ligation) to become pregnant again. The fallopian tubes are reconnected in this reversal surgery. A tubal ligation can't always be ...

  18. Cyclic fatty acyl glycosides in the glandular trichome exudate of Silene gallica.

    PubMed

    Asai, Teigo; Fujimoto, Yoshinori

    2010-08-01

    Chemical investigation of the glandular trichome exudate from Silene gallica L. (Caryophyllaceae) resulted in isolation of 10 cyclic fatty acyl glycosides (gallicasides A-J). The cyclic structures were characterized by a glycosidic linkage of the glucose moiety to either the C-12 or the C-13 position of the octadecanoyl moiety, and by an ester linkage between the C-2 hydroxy group of the glucose moiety and the carboxyl group of the oxygenated octadecanoic acid. The structures of the cyclic fatty acyl glycosides were further distinguished from one another by acetylation and/or malonylation on the glucose moiety. Of these compounds, the 1,2'-cyclic ester of 12(R)-(6-O-acetyl-3-O-malonyl-beta-D-glucopyranosyloxy)octadecanoic acid (gallicaside J) was the most abundant (30.7%). These secondary metabolites were found specifically in the glandular trichome exudate rather than in other aerial parts. PMID:20541780

  19. A galloylated cyanogenic glycoside from the Australian endemic rainforest tree Elaeocarpus sericopetalus (Elaeocarpaceae).

    PubMed

    Miller, Rebecca E; Stewart, Michael; Capon, Robert J; Woodrow, Ian E

    2006-07-01

    A cyanogenic glycoside - 6'-O-galloylsambunigrin - has been isolated from the foliage of the Australian tropical rainforest tree species Elaeocarpus sericopetalus F. Muell. (Elaeocarpaceae). This is the first formal characterisation of a cyanogenic constituent in the Elaeocarpaceae family, and only the second in the order Malvales. 6'-O-galloylsambunigrin was identified as the principal glycoside, accounting for 91% of total cyanogen in a leaf methanol extract. Preliminary analyses indicated that the remaining cyanogen content may comprise small quantities of sambunigrin, as well as di- and tri-gallates of sambunigrin. E. sericopetalus was found to have foliar concentrations of cyanogenic glycosides among the highest reported for tree leaves, up to 5.2 mg CN g(-1) dry wt. PMID:16716370

  20. Organosolv pretreatment of Sitka spruce wood: conversion of hemicelluloses to ethyl glycosides.

    PubMed

    Bouxin, Florent P; David Jackson, S; Jarvis, Michael C

    2014-01-01

    A range of Organosolv pretreatments, using ethanol:water mixtures with dilute sulphuric acid, were applied to Sitka spruce sawdust with the aim of generating useful co-products as well as improving saccharification yield. The most efficient of the pretreatment conditions, resulting in subsequent saccharification yields of up to 86%, converted a large part of the hemicellulose sugars to their ethyl glycosides as identified by GC/MS. These conditions also reduced conversion of pentoses to furfural, the ethyl glycosides being more stable to dehydration than the parent pentoses. Through comparison with the behaviour of model compounds under the same reaction conditions it was shown that the anomeric composition of the products was consistent with a predominant transglycosylation reaction mechanism, rather than hydrolysis followed by glycosylation. The ethyl glycosides have potential as intermediates in the sustainable production of high-value chemicals. PMID:24269088

  1. Two New Quinochalcone C-Glycosides from the Florets of Carthamus tinctorius

    PubMed Central

    Yue, Shijun; Tang, Yuping; Xu, Chengmei; Li, Shujiao; Zhu, Yue; Duan, Jin-Ao

    2014-01-01

    Two new quinochalcone C-glycosides, named hydroxysafflor yellow B (1) and hydroxysafflor yellow C (2), along with two known quinochalcone C-glycosides, safflomin C (3) and saffloquinoside C (4), and one known flavanone, (2R)-4',5-dihydroxyl-6,7-di-O-?-d-glucopyranosyl flavanone (5), were isolated from the florets of Carthamus tinctorius. Their structures were determined by extensive spectroscopic (UV, IR, HR-ESI-MS, 1D and 2D NMR) analyses. In addition, these quinochalcone C-glycosides together with hydroxysafflor yellow A and anhydrosafflor yellow B were evaluated for their anti-oxidative effects against H2O2-induced cytotoxicity in cultured H9c2 cells. Among them, compound 2 exhibited significant anti-oxidative effects. PMID:25247575

  2. Two new quinochalcone C-glycosides from the florets of Carthamus tinctorius.

    PubMed

    Yue, Shijun; Tang, Yuping; Xu, Chengmei; Li, Shujiao; Zhu, Yue; Duan, Jin-Ao

    2014-01-01

    Two new quinochalcone C-glycosides, named hydroxysafflor yellow B (1) and hydroxysafflor yellow C (2), along with two known quinochalcone C-glycosides, safflomin C (3) and saffloquinoside C (4), and one known flavanone, (2R)-4',5-dihydroxyl-6, 7-di-O-?-d-glucopyranosyl flavanone (5), were isolated from the florets of Carthamus tinctorius. Their structures were determined by extensive spectroscopic (UV, IR, HR-ESI-MS, 1D and 2D NMR) analyses. In addition, these quinochalcone C-glycosides together with hydroxysafflor yellow A and anhydrosafflor yellow B were evaluated for their anti-oxidative effects against H2O2-induced cytotoxicity in cultured H9c2 cells. Among them, compound 2 exhibited significant anti-oxidative effects. PMID:25247575

  3. Studies on Kochiae Fructus. V. Antipruritic effects of oleanolic acid glycosides and the structure-requirement.

    PubMed

    Matsuda, H; Dai, Y; Ido, Y; Murakami, T; Matsuda, H; Yoshikawa, M; Kubo, M

    1998-11-01

    We examined the antipruritic effects of various oleanolic acid glycosides from natural medicines such as Kochiae Fructus (the fruit of Kochia scoparia SCHRAD.) and Momordicae Radix (the roots of Momordica cochinchinensis SPRENG.) using a compound 48/80-induced pruritic model in mice. Oleanolic acid 3-O-monodesmosides showed an antipruritic effect, while oleanolic acid 3,28-O-bisdesmosides and their common sapogenol oleanolic acid lacked the activity. This evidence indicated that the 3-O-glycoside moiety and the 28-carboxyl group in oleanolic acid glycosides were essential for exhibiting the antipruritic effect. Furthermore, it was found that the 3-O-glucuronides showed more potent activity than the corresponding 3-O-glucosides. PMID:9853421

  4. Reverse Correlation in Neurophysiology

    ERIC Educational Resources Information Center

    Ringach, Dario; Shapley, Robert

    2004-01-01

    This article presents a review of reverse correlation in neurophysiology. We discuss the basis of reverse correlation in linear transducers and in spiking neurons. The application of reverse correlation to measure the receptive fields of visual neurons using white noise and m-sequences, and classical findings about spatial and color processing in

  5. Differential EI Fragmentation Pathways for Peracetylated C-Glycoside Ketones as a Consequence of Bicyclic Ketal Ring Structures

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Several C-glycoside ketones and peracetylated C-glycoside ketones have been synthesized from 13 structurally-diverse aldoses sugars (including isotope labeled [1-**13C]Glc, [U-**13C]Glc, and [6,6-**2H2]Glc) via an aqueous-based Knoevanagel condensation with aliphatic 1,3-diketones. Sodium adduct m...

  6. Synthesis of phenylazonaphtol-?-D-O-glycosides, evaluation as substrates for beta-glycosidase activity and molecular studies

    PubMed Central

    2014-01-01

    Background Phenylazonaphtol-?-D-O-glycosides are alternative substrates for the detection of enzymatic activity of ?-glycosidases which are involved in various important processes. These azoic compounds are currently exploited as prodrugs for colonic disease due the presence of ?-glycosidase activity in the gut flora and therefore allowing the release of the drug at the specific site. Results Phenylazonaphtol-?-D-O-glucoside 3a and galactoside 3b were prepared via diazonium salt conditions under weak acidic conditions which do not compromise the O-glycosidic bond stability, by coupling reaction between 2-naphtol sodium salt with aminoglycosides 1a and 1b. The resulting phenylazonaphtol glycosides 2a and 2b were deprotected affording the phenylazonaphtol glycosides 3a and 3b in quantitative yield. The galactoside glycoside 3b was assayed as substrate for in vitro ?-galactosidase enzymatic activity showing strong absorbance after releasing of the azoic chromophore. Also, docking studies were performed to determine the best pose as well as the interactions between the ligand and the residues located at the active site. Conclusions The methodology developed for synthesizing the phenylazonaphtol glycosides described proved to be convenient for generating azoic functionalities in the presence of glycosidic bonds and the glycosides suitable as alternative substrates and potentially useful prodrugs in the treatment of colonic diseases. PMID:24995152

  7. A specific binding protein for cardiac glycosides exists in bovine serum.

    PubMed

    Antolovic, R; Kost, H; Mohadjerani, M; Linder, D; Linder, M; Schoner, W

    1998-06-26

    Searching for a binding protein in blood, which may be involved in the specific transport of cardiac glycosides to their receptor sites on the sodium pump, we isolated a cardiac glycoside-binding protein (CGBG) of 26 kDa from the globulin fraction of bovine serum by affinity chromatography and on a ouabain-Sepharose 4B column by a purification factor of 5000. The cardiac glycoside-binding globulin was labeled specifically and covalently by the protein-reactive digoxigenin derivative HDMA (N-hydroxysuccimidyldigoxigenin-3-O-methylcarbonyl-epsilon-+ ++aminocapro ate). Even very high concentrations of other steroids, such as estrogen, testosterone, progesterone, and cortisone, did not prevent HDMA-labeling (at 5 and 100 nM) of CGBG, but the cardenolides ouabain and digoxin or the bufadienolide proscillaridin A did so. CGBG is a homodimer of two 26-kDa subunits forming disulfide bonds, since HDMA labeling of a protein of 53 kDa was observed in SDS-polyacrylamide gel electrophoresis when beta-mercaptoethanol was absent during SDS denaturation. The N-terminal amino acid sequence K-D-V-Y-R-A-P-D-G-T-Q-S-A showed no sequence similarity with proteins recorded in gene and protein sequence data banks. A 90-kDa cytosolic CGBG exists in bovine kidneys and reacts with antibodies against CGBG. Binding of ouabain to the cardiac glycoside-binding globulin was monitored by quenching of intrinsic tryptophan fluorescence. Such studies reveal two negatively cooperative ouabain binding sites with Kd' of 1.52 nM and Kd' = 75 nM and with an interaction factor of 50 using a Koshland-Nmethy-Filmer model. The demonstration of a cardiac glycoside-binding globulin in plasma is consistent with the recent finding of endogenous cardiac glycosides in mammals. PMID:9632685

  8. Temporary reduction of radiation does not permanently reduce flavonoid glycosides and phenolic acids in red lettuce.

    PubMed

    Becker, Christine; Klring, Hans-Peter; Kroh, Lothar W; Krumbein, Angelika

    2013-11-01

    Applying transparent daytime screens in greenhouses in cool seasons reduces the amount of energy needed for heating, but also the solar radiation available for crops. This can reduce yield and product quality of leafy vegetables because of constrained photosynthesis and altered biosynthesis. To study this, we cultivated five-week old red leaf lettuce (Lactuca sativa L.) for four weeks in growth chambers under a photosynthetic photon flux density (PPFD) of 225 and 410 ?mol m(-2) s(-1), respectively. Some plants were exchanged between radiation intensities after two weeks. We investigated the concentration of five flavonoid glycosides, three caffeic acid derivatives, reducing sugars as well as plant growth. Remarkably, no significant influence of radiation intensity on the concentration of phenolic acids or anthocyanin glycosides was observed. In contrast, quercetin and luteolin glycoside concentration was between 14 and 34% lower in plants growing under lower compared to higher PPFD. Already after two weeks of cultivation, plants grown under lower PPFD contained less quercetin and luteolin glycosides but they completely compensated if subsequently transferred to higher PPFD until harvest. Hence, marketable lettuce heads which experienced temporary shading followed by an unshaded phase did not contain lower concentrations of flavonoid glycosides or phenolic acids. Also, there was no reduction of head mass in this variant. Our results suggest that saving energy in early growth stages is feasible without losses in yield or health promoting phenolic substances. In addition, there was a close correlation between the concentration of reducing sugars and some flavonoid glycosides, indicating a close metabolic connection between their biosynthesis and the availability of carbohydrates. PMID:23735845

  9. Angiotensin-converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides.

    PubMed

    Charles, Rajachristu Einstein; Ponrasu, Thangavel; Sivakumar, Ramaiah; Divakar, Soundar

    2009-03-01

    Amyloglucosidase from Rhizopus mould and beta-glucosidase from sweet almond were employed for the preparation of phenolic and vitamin glycosides of vanillin, N-vanillylnonanamide, DL-dopa, dopamine, curcumin, alpha-tocopherol (vitamin E), pyridoxine (vitamin B(6)), ergocalciferol (vitamin D(2)), thiamin (vitamin B(1)) and riboflavin (vitamin B(2)). Approx. 20 enzymatically prepared phenolic and vitamin glycosides were subjected to ACE (angiotensin-converting enzyme) inhibition activity measurements, and 14 glycosides were tested for antioxidant activities. Both phenolic and vitamin glycosides exhibited IC(50) values for ACE inhibition in the 0.52+/-0.03-3.33+/-0.17 mM range and antioxidant activities ranging from 0.8+/-0.04 to 1.18+/-0.06 mM. Comparable ACE inhibition values were observed between free phenols and vitamin glycosides. However, antioxidant activities of glycosides were, in general, lesser than those of free phenols. Best IC(50) value for ACE inhibition were observed for 11-O-(D-fructofuranosyl)thiamin (0.52+/-0.03 mM), 3-hydroxy-4-O-(6-D-sorbitol)phenylalanine (0.56+/-0.03 mM), 4-O-(beta-D-glucopyranosyl)vanillin (0.61+/-0.03 mM), 4-O-(D-galactopyranosyl)vanillin (0.61+/-0.03 mM) and pyridoxine-D-glucoside (0.84+/-0.04 mM). Similarly, best IC(50) values for antioxidant activity were observed for 1,7-O-(bis-beta-D-glucopyranosyl)curcumin (0.8+/-0.04 mM), 4-O-(beta-D-glucopyranosyl)vanillin (0.9+/-0.05 mM), 3-hydroxy-4-O-(beta-D-galactopyranosyl-(1'-->4)beta-D-glucopyranosyl)phenylalanine (0.9+/-0.05 mM), 20-O-(D-glucopyranosyl)ergocalciferol (0.9+/-0.05 mM) and dopamine-D-galactoside (0.93+/-0.05 mM). PMID:18547170

  10. Cholestane steroid glycosides from the rhizomes of Dioscorea villosa (wild yam).

    PubMed

    Ali, Zulfiqar; Smillie, Troy J; Khan, Ikhlas A

    2013-04-01

    Phytochemical investigation of the MeOH extract of Dioscorea villosa rhizomes resulted in the isolation of two new bidesmosidic cholestane steroid glycosides, dioscoreavillosides A and B (1 and 2). In addition, the extract yielded 12 previously known furostan and spirostan steroid glycosides (3-14), along with diosgenin (15). Compounds 3-7, 9, 14, and 15 were isolated for the first time from D. villosa. The structures of the isolated compounds were determined using spectroscopic and chemical methods including 1D and 2D NMR. The antimicrobial action of most of these compounds was tested against five fungal and five bacterial strains. PMID:23454141

  11. A New Diterpene Glycoside: 15?-Hydroxy-Rebaudioside M Isolated from Stevia rebaudiana.

    PubMed

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

    2015-07-01

    In a continued search for novel diterpenoid glycosides, we recently isolated and characterized a Rebaudioside M derivative with a hydroxyl group at position 15 in the central diterpene core from an extract of Stevia rebaudiana Bertoni. Here we report the complete structure elucidation of 15?-hydroxy-Rebaudioside M (2) on the basis of NMR (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D TOCSY, NOESY) and mass spectral data. Steviol glycoside with a hydroxyl group at C-15 in the central diterpene core has not been previously reported. PMID:26410999

  12. Cholestane steroid glycosides from the root of Dioscorea villosa (wild yam)

    PubMed Central

    Ali, Zulfiqar; Smillie, Troy J.; Khan, Ikhlas A.

    2014-01-01

    Phytochemical investigation of the MeOH extract of Dioscorea villosa root resulted in the isolation of two new bidesmosidic cholestane steroid glycosides, dioscoreavillosides A and B (1 and 2). In addition, the extract yielded 12 previously known furostane and spirostane steroid glycosides (3-14), along with diosgenin (15). Compounds 3-7, 9, 14, and 15 were isolated for the first time from D. villosa. The structures of the isolated compounds were determined using spectroscopic and chemical methods including 1D and 2D NMR. The antimicrobial action of most of these compounds was tested against five fungal and five bacterial strains. PMID:23454141

  13. Electrospray ionization mass spectrometry of mixtures of triterpene glycosides with L-phenylalanine

    NASA Astrophysics Data System (ADS)

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

    2011-09-01

    Electrospray-ionization mass spectrometry (ESI-MS) was used to investigate for the first time the molecular complexation of L-phenylalanine with hederagenin 3-O- ?- L-rhamnopyranosyl-(1 ? 2)-O- ?- L-arabinopyranoside ( ?-hederin) and its 28-O- ?- L-rhamnopyranosyl-(1 ? 4)-O-?- D-glucopyranosyl-(1 ? 6)-O-?- D-glucopyranosyl ester (hederasaponin C). The glycoside/ L-phenylalanine complexes with a 1:1 molar ratio turned out to be most stable. The structures of the glycosides and L-phenylalanine have been concluded to have an impact on the complexation process.

  14. Microcystbiopterins A-E, five O-methylated biopterin glycosides from two Microcystis spp. bloom biomasses.

    PubMed

    Lifshits, Marina; Kovalerchik, Dimitri; Carmeli, Shmuel

    2016-03-01

    Five previously undescribed biopterin glycosides, microcystbiopterin A-E, were isolated from the extracts of two bloom materials of Microcystis spp. collected from a fishpond (IL-337) and Lake Kinneret (IL-347), Israel. The structure of the pterins was established by interpretation of their UV, CD, 1D and 2D NMR spectra and HR mass measurements. Microcystbiopterin D is the first heptose containing pterin glycoside to be reported in the literature. Their antimicrobial and cytotoxic properties were evaluated but all were found not active in both assays. PMID:26804212

  15. Syntheses of retinol glycosides using beta-glucosidase in SCCO(2) media.

    PubMed

    Einstein Charles, Rajachristu; Ponrasu, Thangavel; Sankar, Kadimi Udaya; Divakar, Soundar

    2009-10-01

    beta-Glucosidase isolated from sweet almond catalyzed syntheses of water soluble retinol glycosides were carried out in SCCO(2) media with carbohydrates-D-glucose 2, D-galactose 3, D-mannose 4, D-fructose 5, and D-sorbitol 6. Retinol glycosides yields were in the 9-34% range. Reaction with D-fructose 5 gave a highest yield of 34%. Excellent regioselectivity was observed with D-mannose 4 and D-sorbitol 6 which gave exclusively C1beta-mannoside and C1-D-sorbitolide. PMID:19005623

  16. Phenolic glycosides and other constituents from the bark of Magnolia officinalis.

    PubMed

    Yan, Ren-Yi; Liu, Hong-Liang; Zhang, Jian-Yong; Yang, Bin

    2014-01-01

    A new phenolic glycoside, syringic acid 4-O-?-D-glucopyranosyl-(1 ? 5)-?-L-rhamnopyranoside (1), together with 12 known compounds consisting of eight phenolic glycosides (2-9), two phenolic acids (10 and 11), and two norsesquiterpenoids (12 and 13), was isolated from the methanol extract of the bark of Magnolia officinalis. Their structures were elucidated on the basis of spectroscopic analysis and chemical methods. Compounds 1-11 were evaluated for their inhibitory activities against fructose-1,6-bisphosphatase, aldose reductase, lipase, dipeptidyl peptidase-IV, ?-glucosidase, and three cancer cell lines. However, all the compounds showed weak or no activities in these tests. PMID:23909378

  17. Oplopanphesides A-C, three new phenolic glycosides from the root barks of Oplopanax horridus.

    PubMed

    Huang, Wei-Hua; Zhang, Qing-Wen; Meng, Lan-Zhen; Yuan, Chun-Su; Wang, Chong-Zhi; Li, Shao-Ping

    2011-01-01

    Three new phenolic glycosides, named oplopanphesides A-C (1-3), have been isolated from the root barks of Oplopanax horridus. Their structures were elucidated by a combination of spectroscopic analyses, including 1D- and 2D-NMR techniques. These phenolic glycosides possess a novel feature in their sugar moieties that a 3-hydroxy-3-methylglutaryl moiety was connected with C-6 of the ?-D-glucopyranosyl group. Those compounds showed no cytotoxic effects against human cancer cell lines (MDA-231 and MCF-7) by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. PMID:21532210

  18. Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

    PubMed Central

    2014-01-01

    A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the C-linked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC50 values in micromolar range and low cytotoxicity offering new HITS for further exploration. PMID:25147607

  19. New Labdane Diterpenes and Their Glycoside Derivatives from the Roots of Isodon adenantha.

    PubMed

    Wu, La-Bin; Xiao, Chao-Jiang; Jiang, Xue; Qiu, Lin; Dong, Xiang; Jiang, Bei

    2015-08-01

    Two new labdane-type diterpenes (adenanthic acids A and B; 1 and 2, resp.) and three new labdane diterpene glycosides (adenanthosides A-C; 3-5, resp.) were isolated from the roots of Isodon adenantha, together with 23 known constituents including seven diterpenoids (6-12), eight triterpenoids (13-20), one lignan glycoside (21), six steroids (22-27), and one ceramide (28). Their structures were elucidated by spectroscopic methods including extensive 2D-NMR techniques. Cytotoxicity and antibacterial activities of the samples were measured by the MTT method and the filter paper disc agar diffusion method. But none of them showed significant activities. PMID:26265575

  20. A steryl glycoside fraction with hemolytic activity from tubers of Momordica cochinchinensis.

    PubMed

    Ng, T B; Li, W W; Yeung, H W

    1986-10-01

    A hemolytic fraction has been obtained from fresh tubers of Momordica cochinchinensis. The fraction was strongly adsorbed on DEAE-Sepharose CL6B. It did not stain with Coomassie brilliant blue in SDS-polyacrylamide gel electrophoresis and it gave no immunoprecipitin arcs in immunoelectrophoresis. The hemolytic activity of the fraction was resistant to heat and proteolytic enzymes. The behavior of the fraction in thin-layer chromatography and its positive reaction in Liebermann-Burchard test indicated that the hemolytic activity of the fraction can be attributed to a steryl glycoside(s). PMID:3821135

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

    NASA Astrophysics Data System (ADS)

    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.

  2. Inhibition of influenza virus multiplication by N-glycosides of benzimidazoles-N.

    PubMed

    TAMM, I; FOLKERS, K; SHUNK, C H; HORSFALL, F L

    1954-03-01

    Chloro derivatives of benzimidazole were found to be 2 to 3 times more active than corresponding methyl derivatives in causing inhibition of Lee virus multiplication in chorioallantoic membrane cultures in vitro. The most active benzimidazole derivative thus far tested is 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB); it caused 75 per cent inhibition of Lee virus multiplication in membrane cultures at a concentration of 0.38 x 10(-4)M. On the other hand, 5,6-dimethyl-1-alpha;-D-ribofuranosylbenzimidazole, the moiety present in vitamin B(12), failed to inhibit Lee virus multiplication at a concentration of 35 x 10(-4)M. Other N-glycosides of 5,6-dichlorobenzimidazole were considerably less active than DRB. In single cycle experiments, the degree of inhibition of Lee virus multiplication by DRB in membrane cultures was not dependent on the amount of virus in the inoculum. This compound did not inactivate the infectivity of extracellular Lee virus, had no effect on virus-erythrocyte interaction, did not interfere with the adsorption of the virus by the host tissue, nor affect the release of newly formed virus from the membrane. The inhibitory effect of DRB on Lee virus multiplication, in contrast to that of 2,5-dimethylbenzimidazole, persisted after transfer of infected membranes into fresh culture medium not containing the compound. Both DRB and the 2,5-dimethyl compound caused 99 per cent inhibition of Lee virus multiplication without affecting oxygen uptake of the membrane. Tissue proliferation of membrane pieces in roller tube culture was not significantly affected by DRB at inhibitory concentration, whereas at equivalent concentration the 2,5-dimethyl compound did restrict cellular growth. At higher concentrations, both compounds caused retardation of cell proliferation. This effect was reversible on removal of either compound from the medium. The multiplication of several strains of influenza A and B viruses, i.e. Lee, MB, PR8, and FM1, was inhibited to the same degree by each of the two compounds; DRB was 35 times more active than the 2,5-dimethyl compound relative to each of the strains. DRB caused inhibition of Lee virus multiplication in intact embryonated chicken eggs and in mice without causing significant signs of toxicity in either host. Some of the implications of these findings are discussed in relation to the mechanism of the inhibition of influenza virus multiplication. PMID:13130796

  3. Systematic screening and characterization of glycosides in tobacco leaves by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry using neutral loss scan and product ion scan.

    PubMed

    Ding, Li; Wang, Xiaoyu; Wang, Sheng; Yu, Jingjing; Qin, Yaqiong; Zhang, Xiaobing; Xie, Fuwei

    2015-12-01

    Glycosides in tobacco leaves are highly important aromatic precursors. It is necessary to reveal glycosides in tobacco leaves to improve tobacco planting and processing. This study describes a method for the systematic screening of glycosides in tobacco leaves by liquid chromatography with tandem mass spectrometry. Although glycosides contain numerous aglycones, the number of glycans is limited. Based on a screening table of glycans designed for neutral loss scan, glycosides with different aglycones were systematically screened out. Then, the MS(2) fragment spectra of scanned glycosides were further obtained using product ion scan. By comparison with the spectra in online tandem mass spectral databases, reported references, and verification by commercial standards, 64 glycosides were detected, including 39 glycosides linked with monosaccharides, 18 glycosides linked with disaccharides and 7 glycosides linked with trisaccharides. It is noteworthy that glycosides linked with trisaccharides have previously been rarely reported in tobacco. This method appears to be a useful tool for the systematic screening and characterization of glycosides in tobacco and can potentially be applied to other plants. PMID:26412345

  4. Reversal of Oral Anticoagulation

    PubMed Central

    Limdi, Nita A.

    2013-01-01

    Although the use of dabigatran and rivaroxaban are increasing, data on reversal of their effects are limited. The lack of reliable monitoring methods and specific reversal agents renders treatment strategies empirical and as a result, , treatment consists mainly of supportive measures. Therefore, we performed a systematic search of the PubMed database to find studies and reviews pertaining to oral anticoagulation reversal strategies. This review discusses current anticoagulation reversal recommendations for the oral anticoagulants warfarin, dabigatran, and rivaroxaban for patients at a heightened risk of bleeding, actively bleeding or those in need for pre-procedural anticoagulation reversal. We highlight the literature that shaped these recommendations and provide directions for future research to address knowledge gaps. While reliable recommendations are available for anticoagulation reversal in patients treated with warfarin, guidance on reversal of dabigatran and rivaroxaban is varied and equivocal. Given the increasing use of the newer agents, focused research is needed to identify effective reversal strategies and develop and implement an accurate method (assay) to guide reversal of the newer agents. Determining patient-specific factors that influence the effectiveness of reversal treatments and comparing the effectiveness of various treatment strategies are pertinent areas for future anticoagulation reversal research. PMID:23606318

  5. Characterization and Modeling of the Collision Induced Dissociation Patterns of Deprotonated Glycosphingolipids: Cleavage of the Glycosidic Bond.

    PubMed

    Roman, Marko

    2016-01-01

    Glycosphingolipid fragmentation behavior was investigated by combining results from analysis of a series of negative ion tandem mass spectra and molecular modeling. Fragmentation patterns extracted from 75 tandem mass spectra of mainly acidic glycosphingolipid species (gangliosides) suggest prominent cleavage of the glycosidic bonds with retention of the glycosidic oxygen atom by the species formed from the reducing end (B and Y ion formation). Dominant product ions arise from dissociation of sialic acids glycosidic bonds whereas product ions resulting from cleavage of other glycosidic bonds are less abundant. Potential energy surfaces and unimolecular reaction rates of several low-energy fragmentation pathways leading to cleavage of glycosidic bonds were estimated in order to explain observed dissociation patterns. Glycosidic bond cleavage in both neutral (unsubstituted glycosyl group) and acidic glycosphingolipids was the outcome of the charge-directed intramolecular nucleophilic substitution (SN2) mechanism. According to the suggested mechanism, the nucleophile in a form of carboxylate or oxyanion attacks the carbon at position one of the sugar ring, simultaneously breaking the glycosidic bond and yielding an epoxide. For gangliosides, unimolecular reaction rates suggest that dominant product ions related to the cleavage of sialic acid glycosidic bonds are formed via direct dissociation channels. On the other hand, low abundant product ions related to the dissociation of other glycosidic bonds are more likely to be the result of sequential dissociation. Although results from this study mainly contribute to the understanding of glycosphingolipid fragmentation chemistry, some mechanistic findings regarding cleavage of the glycosidic bond may be applicable to other glycoconjugates. Graphical Abstract ?. PMID:26297186

  6. Evaluation of the glycoside hydrolase activity of a Brettanomyces strain on glycosides from sour cherry (Prunus cerasus L.) used in the production of special fruit beers.

    PubMed

    Daenen, Luk; Sterckx, Femke; Delvaux, Freddy R; Verachtert, Hubert; Derdelinckx, Guy

    2008-11-01

    The glycoside hydrolase activity of Saccharomyces cerevisiae and Brettanomyces custersii was examined on sour cherry (Prunus cerasus L.) glycosides with bound volatile compounds. Refermentations by the beta-glucosidase-negative S. cerevisiae strains LD25 and LD40 of sour cherry juice-supplemented beer demonstrated only a moderate increase of volatiles. In contrast, the beta-glucosidase-positive B. custersii strain LD72 showed a more pronounced activity towards glycosides with aliphatic alcohols, aromatic compounds and terpenoid alcohols. Important contributors to sour cherry aroma such as benzaldehyde, linalool and eugenol were released during refermentation as shown by analytical tools. A gradually increasing release was observed during refermentations by B. custersii when whole sour cherries, sour cherry pulp or juice were supplemented in the beer. Refermentations with whole sour cherries and with sour cherry stones demonstrated an increased formation of benzyl compounds. Thus, amygdalin was partially hydrolysed, and a large part of the benzaldehyde formed was mainly reduced to benzyl alcohol and some further esterified to benzyl acetate. These findings demonstrate the importance and interesting role of certain Brettanomyces species in the production of fruit lambic beers such as 'Kriek'. PMID:18673394

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

    PubMed

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

    2013-01-01

    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. PMID:24352020

  8. Initial Optimization of a New Series of ?-Secretase Modulators Derived from a Triterpene Glycoside.

    PubMed

    Fuller, Nathan O; Hubbs, Jed L; Austin, Wesley F; Creaser, Steffen P; McKee, Timothy D; Loureiro, Robyn M B; Tate, Barbara; Xia, Weiming; Ives, Jeffrey L; Findeis, Mark A; Bronk, Brian S

    2012-11-01

    The discovery of a new series of ?-secretase modulators is disclosed. Starting from a triterpene glycoside ?-secretase modulator that gave a very low brain-to-plasma ratio, initial SAR and optimization involved replacement of a pendant sugar with a series of morpholines. This modification led to two compounds with significantly improved central nervous system (CNS) exposure. PMID:24900406

  9. An anti-inflammatory and anti-microbial flavone glycoside from flowers of Cleome viscosa

    PubMed Central

    2012-01-01

    Background Natural products isolated from plant sources have been demonstrated as potential candidates against several ailments. The scientific investigations on the underlying principles of phytotherapy can pave way for the convergence of traditional medicines and modern science and technologies. Results Quercetin 3-O-(2??-acetyl)-glucoside obtained from ethyl acetate fraction of Cleome viscosa is studied against inflammatory of carrageenan-induced rat paw edema ( in vivo) and microbial activity on ( in vitro). The structure of the glycoside is confirmed by means of hydrogen-1 nuclear magnetic resonance spectroscopy, carbon nuclear magnetic resonance spectroscopy, attached proton test, and mass spectrum. The flavonoid glycoside showed significant anti-inflammatory activity of on carrageenan-induced rat paw edema ( in vivo) and anti-microbial activity ( in vitro) on Staphylococcus aureus (gram positive) and Escherichia coli (gram negative). The anti-inflammatory effect of the flavonoid glycoside may be due to the inhibition of prostaglandin synthesis. Selective toxicity with flavonoid glycoside towards the gram-positive bacteria was found on S. aureus. Conclusions The present study reveals the anti-inflammatory and antimicrobial activities of an isolated quercetin 3-O-(2??-acetyl)-glucoside from a natural source ( C. viscosa). PMID:22613049

  10. Highly active -xylosidases of glycoside hydrolase family 43 operating on natural and artificial substrates

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The hemicellulose xylan constitutes a major portion of plant biomass, a renewable feedstock available for conversion to biofuels and other bioproducts. -xylosidase operates in the deconstruction of the polysaccharide to fermentable sugars. Glycoside hydrolase family 43 has been identified as a so...

  11. A direct route to 2-(beta-D-ribofuranosylthio)pyridine glycosides.

    PubMed

    Elgemeie, Galal H; Heikel, Abdel-Fatah Z; Ahmed, Mona A

    2002-01-01

    A novel synthesis of a new class of 2-(beta-D-ribofuranosylthio)pyridine glycosides utilizing the reactions of substituted pyridine-2(1H)-thiones and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose as starting components is described. PMID:12442958

  12. A New ent-Labdane Diterpene Glycoside form the Leaves of Casearia sylvestris

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Sylvestin (1), a new ent-labdane glycoside, was isolated from the leaves of Casearia sylvestris. The structure was determined on the basis of 1D and 2 D NMR and HR-ESI-MS analyses. The diterpenoid of ent-labdane type was isolated for the first time from C. sylvestris....

  13. Reinvestigation of the stereochemistry of the C-glycosidic ellagitannins, vescalagin and castalagin.

    PubMed

    Matsuo, Yosuke; Wakamatsu, Hatsumi; Omar, Mohamed; Tanaka, Takashi

    2015-01-01

    The stereochemistry of the C-glycosidic ellagitannins, vescalagin and castalagin, has been reinvestigated using computational methods. DFT calculations of their (1)H and (13)C NMR spectra, as well as TDDFT calculations of the ECD spectra of their des-hexahydroxydiphenoyl analogues, revealed that the structure of the triphenoyl moiety of vescalagin and castalagin should be revised. PMID:25496565

  14. Cloning, Expression and Characterization of a Glycoside Hydrolase Family 39 Xylosidase from Bacillus Halodurans C-125

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The gene encoding a glycoside hydrolase family 39 xylosidase (BH1068) from the alkaliphile Bacillus halodurans strain C-125 was cloned with a C-terminal His-tag and the recombinant gene product termed XylBH1068 was expressed in E. coli. Of the artificial substrates tested, XylBH1068 hydrolyzed nitro...

  15. Differential El Ion Fragmentation Pathways for Peracetylated C-Glycoside Ketals

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Aqueous-based Knoevenagel condensation of sugars with beta-diketones is a useful method for preparing beta-C-glycoside ketones. A mechanism has been proposed in which C-C bond formation between the anomeric sugar carbon and the bridged methylene of the diketone is followed by beta-elimination of wa...

  16. KOLOKOSIDES A-D: TRITERPENOID GLYCOSIDES FROM A HAWAIIAN ISOLATE OF XYLARIA SP.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Four new triterpenoid glycosides, kolokosides A-D (1-4), along with the known compound 19, 20-epoxycytochalasin N, were isolated from cultures of a Hawaiian wood-decay fungus (Xylaria sp.) The structures and relative configurations of 1-4 were determined primarily by analysis of NMR data, and the ab...

  17. DFT STUDY OF ALPHA-MALTOSE: INFLUENCE OF HYDROXYL ORIENTATIONS ON THE GLYCOSIDIC BOND

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The result of DFT geometry optimization of 68 unique alpha-maltose conformers at the B3LYP/6-311++G** level of theory is described. Particular attention is paid to the hydroxyl group rotational positions and their influence on the glycosidic bond dihedral angles. The orientation of lone pair elect...

  18. Theoretical Calculation of Electronic Circular Dichroism of a Hexahydroxydiphenoyl-Containing Flavanone Glycoside

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Time-dependent density functional theory (TDDFT) was employed for theoretical calculation of electronic circular dichroism (ECD) of a hexahydroxydiphenoyl (HHDP)-containing flavanone glycoside, mattucinol-7-O-[4'',6''-O-(aS)-hexahydroxydiphenoyl]-ß-d-glucopyranoside (2). It identified the roles of t...

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

    PubMed

    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. PMID:19544362

  20. New oleanan-type triterpene and cincholic acid glycosides from Peruvian "Ua de Gato" (Uncaria tomentosa).

    PubMed

    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. PMID:15467250

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

    PubMed

    Zhu, Dapeng; Yu, Biao

    2015-12-01

    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. PMID:26595819

  2. Clerodane and Ent-kaurane Diterpene Glycosyl and Glycoside Derivatives from the Leaves of Casearia sylvestris

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Five new clerodane diterpene glycosides caseariasides A-E (1-4) and three new ent-kaurane diterpene glucosides sylvestrisides C-E (6-8) were isolated from the leaves of Casearia sylvestris. Their structures were determined on the basis of chemical and spectroscopic analyses....

  3. Characterization of two-step deglycosylation via oxidation by glycoside oxidoreductase and defining their subfamily

    PubMed Central

    Kim, Eun-Mi; Seo, Joo-Hyun; Baek, Kiheon; Kim, Byung-Gee

    2015-01-01

    Herein, we report a two-step deglycosylation mediated by the oxidation of glycoside which is different from traditional glycoside hydrolase (GH) mechanism. Previously, we reported a novel flavin adenine dinucleotide (FAD)-dependent glycoside oxidoreductase (FAD-GO) having deglycosylation activity. Various features of the reaction of FAD-GO such as including mechanism and catalytic residue and substrate specificity were studied. In addition, classification of novel FAD-GO subfamily was attempted. Deglycosylation of glycoside was performed spontaneously via oxidation of 3-OH of glycone moiety by FAD-GO mediated oxidation reaction. His493 residue was identified as a catalytic residue for the oxidation step. Interestingly, this enzyme has broad glycone and aglycon specificities. For the classification of FAD-GO enzyme subfamily, putative FAD-GOs were screened based on the FAD-GO from Rhizobium sp. GIN611 (gi 365822256) using BLAST search. The homologs of R. sp. GIN611 included the putative FAD-GOs from Stenotrophomonas strains, Sphingobacterium strains, Agrobacterium tumefaciens str. C58, and etc. All the cloned FAD-GOs from the three strains catalyzed the deglycosylation via enzymatic oxidation. Based on their substrate specificities, deglycosylation and oxidation activities to various ginsenosides, the FAD-GO subfamily members can be utilized as novel biocatalysts for the production of various aglycones. PMID:26057169

  4. IDENTIFICATION OF FLAVONE AGLYCONES AND GLYCOSIDES IN SOYBEAN PODS BY LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY

    Technology Transfer Automated Retrieval System (TEKTRAN)

    High-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry (HPLC-APCI-MS) was used to identify flavone aglycones and glycosides in soybean pods. Tandem mass spectrometry (MS/MS and MS3) and photodiode array detection were also utilized in flavone characterizat...

  5. Neoadenoloside A, a highly functionalized diterpene C-glycoside, from Isodon adenolomus.

    PubMed

    Zhao, Wei; Wang, Wei-Guang; Li, Xiao-Nian; Du, Xue; Zhan, Rui; Zou, Juan; Li, Yan; Zhang, Hai-Bo; He, Fei; Pu, Jian-Xin; Sun, Han-Dong

    2012-08-11

    Neoadenoloside A (1), an unprecedented diterpene C-glycoside with a unique C(26) framework, along with lasiokaurin (3) were isolated from the leaves of Isodon adenolomus. The absolute configuration of 2, a derivative of 1, was determined by spectroscopic methods and single-crystal X-ray diffraction analysis. PMID:22743545

  6. A GH57 4-?-glucanotransferase of hyperthermophilic origin with potential for alkyl glycoside production.

    PubMed

    Paul, Catherine J; Leemhuis, Hans; Dobruchowska, Justyna M; Grey, Carl; nnby, Linda; van Leeuwen, Sander S; Dijkhuizen, Lubbert; Karlsson, Eva Nordberg

    2015-09-01

    4-?-Glucanotransferase (GTase) enzymes (EC 2.4.1.25) modulate the size of ?-glucans by cleaving and reforming ?-1,4 glycosidic bonds in ?-glucans, an essential process in starch and glycogen metabolism in plants and microorganisms. The glycoside hydrolase family 57 enzyme (GTase57) studied in the current work catalyzes both disproportionation and cyclization reactions. Amylose was converted into cyclic amylose (with a minimum size of 17 glucose monomers) as well as to a spectrum of maltodextrins, but in contrast to glycoside hydrolase family 13 cyclodextrin glucanotransferases (CGTases), no production of cyclodextrins (C6-C8) was observed. GTase57 also effectively produced alkyl-glycosides with long ?-glucan chains from dodecyl-?-D-maltoside and starch, demonstrating the potential of the enzyme to produce novel variants of surfactants. Importantly, the GTase57 has excellent thermostability with a maximal activity at 95 C and an activity half-life of 150 min at 90 C which is highly advantageous in this manufacturing process suggesting that enzymes from this relatively uncharacterized family, GH57, can be powerful biocatalysts for the production of large head group glucosides from soluble starch. PMID:25693671

  7. Rehabilitation of faulty kinetic determinations and misassigned glycoside hydrolase family of retaining mechanism ß-xylosidases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We obtained Cx1 from a commercial supplier, whose catalog listed it as a ß-xylosidase of glycoside hydrolase family 43. NMR experiments indicate retention of anomeric configuration in its reaction stereochemistry, opposing the assignment of GH43, which follows an inverting mechanism. Partial protein...

  8. Synergistic effect of isoflavone glycosides and fructooligosaccharides on postgastrectomy osteopenia in rats

    PubMed Central

    Kimira, Yoshifumi; Tajima, Kiyono; Ohta, Atsutane; Ishimi, Yoshiko; Katsumata, Shin-ichi; Suzuki, Kazuharu; Adlercreutz, Herman; Uehara, Mariko

    2012-01-01

    Fructooligosaccharides stimulate the growth of Bifidobacteria, which cleave isoflavone glycosides to yield corresponding aglycones, and convert metabolites by enhancing enterohepatic recirculation of isoflavones in rats. In the present study, we determined the synergistic effect of dietary isoflavone glycosides and fructooligosaccharides on postgastrectomy osteopenia in rats. Nine-week-old male Sprague-Dawley rats were gastrectomized (n = 20) or sham operated, (control, n = 5) and then randomly assigned to 5 diet groups: sham-a purified diet control, gastrectomized-control, gastrectomized-isoflavone (0.2% isoflavone glycosides), gastrectomized-fructooligosaccharides (7.5% fructooligosaccharides), and isoflavone and fructooligosaccharides (0.2% isoflavone glycosides + 7.5% fructooligosaccharides). After 6 weeks, the rats were killed and biological samples were collected. In gastrectomized rats, fructooligosaccharides prevented femoral bone fragility, but isoflavone without fructooligosaccharides did not inhibit postgastrectomy osteopenia. Isoflavone and fructooligosaccharides exhibited a synergistic in the distal metaphyseal trabecular bone, indicated by peripheral quantitative computed tomography. Moreover, fructooligosaccharides increased calcium absorption and equol production from daidzein in gastrectomized rats. These results indicate that isoflavone alone did not inhibit postgastrectomy osteopenia, but the combination of isoflavone and fructooligosaccharides improved the inhibition of trabecular bone loss by increasing calcium absorption and equol production through fructooligosaccharides supplementation. PMID:22962536

  9. Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions

    PubMed Central

    Talisman, Ian J.; Kumar, Vineet; Deschamps, Jeffrey R.; Frisch, Mark

    2011-01-01

    We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methyl-1H-imidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl)imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography, and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the ? isomer regardless of neighboring group effects. PMID:21911215

  10. Anti-hepatitis B virus activities and absolute configurations of sesquiterpenoid glycosides from Phyllanthus emblica.

    PubMed

    Lv, Jun-Jiang; Wang, Ya-Feng; Zhang, Jing-Min; Yu, Shan; Wang, Dong; Zhu, Hong-Tao; Cheng, Rong-Rong; Yang, Chong-Ren; Xu, Min; Zhang, Ying-Jun

    2014-11-21

    During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1G8 (18) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6G8 (68) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory. The sesquiterpenoid glycoside dimers 69 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 0.97 and 5.68 1.75 ?M towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively. PMID:25268491

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  12. Flavonol glycosides from Epimedium sagittatum and their neurite outgrowth activity on PC12h cells.

    PubMed

    Kuroda, M; Mimaki, Y; Sashida, Y; Umegaki, E; Yamazaki, M; Chiba, K; Mohri, T; Kitahara, M; Yasuda, A; Naoi, N; Xu, Z W; Li, M R

    2000-08-01

    The MeOH extract of Epimedium sagittatum was found to show neurite outgrowth activity on cultured PC12h cells. Bioassay-guided fractionation of the MeOH extract yielded six prenylated flavonol glycosides, ikarisoside A (1), icarisid II (2), epimedoside A (3), icariin (4), epimedin B (5), and epimedokoreanoside-I (6) as the active ingredients. PMID:10985091

  13. Flavonoid glycosides from the leaves of Cissus ibuensis hook (vitaceae).

    PubMed

    Ahmadu, A A; Onanuga, A; Aquino, R

    2010-01-01

    The bioactive N-butanol fraction of the ethanol extract of the leaves of Cissus ibuensis was fractionated over silica Gel column to give Quercetin 3-O-rutinoside (I) and mixtures of Flavonoids (A2). A2 was fractionated using reverse phase HPLC to give Kaempferol 3-O-?-rhamnopyranosyl (1?6)-?-D-galactopyranoside (II), Kaempferol 3-O-rutinoside(III) and Kaempferol3-O-?-rhamnopyranosyl (1?6)-?-rhamnopyranosyl(1?2)-?-D-galactopyranoside (IV). The structures were elucidated by NMR spectroscopy and compared with literature. PMID:21461150

  14. Vasectomy reversal in humans.

    PubMed

    Bernie, Aaron M; Osterberg, E Charles; Stahl, Peter J; Ramasamy, Ranjith; Goldstein, Marc

    2012-10-01

    Vasectomy is the most common urological procedure in the United States with 18% of men having a vasectomy before age 45. A significant proportion of vasectomized men ultimately request vasectomy reversal, usually due to divorce and/or remarriage. Vasectomy reversal is a commonly practiced but technically demanding microsurgical procedure that restores patency of the male excurrent ductal system in 80-99.5% of cases and enables unassisted pregnancy in 40-80% of couples. The discrepancy between the anastomotic patency rates and clinical pregnancy rates following vasectomy reversal suggests that some of the biological consequences of vasectomy may not be entirely reversible in all men. Herein we review what is known about the biological sequelae of vasectomy and vasectomy reversal in humans, and provide a succinct overview of the evaluation and surgical management of men desiring vasectomy reversal. PMID:23248768

  15. High sensitivity of the Na+, K+-pump of human red blood cells to genins of cardiac glycosides.

    PubMed

    Senn, N; Lelivre, L G; Braquet, P; Garay, R

    1988-04-01

    1. Four different cardiac glycosides (ouabain, digitoxin, digoxin and gitoxin) and their corresponding genins were tested on Na+, K+-pump fluxes measured under steady-state and initial rate conditions (non equilibrium conditions) in human and rat erythrocytes and in mouse macrophages. 2. In human red cells, Na+, K+-pump fluxes exhibited up to 8 fold higher sensitivity to genins than to glycosides. In addition genins, but not the corresponding glycosides, exhibited double reactivity with regard to the erythrocyte Na+, K+-pump (with the exception of gitoxigenin). A weak reactivity component was similar to the one of the corresponding glycosides (IC50 of about 10(-6) M) and a high reactivity component exhibited IC50 values varying from 0.1 to 0.5 X 10(-6) M for digitoxigenin and ouabagenin respectively. 3. In contrast with human red cells, the initial rate of Na+, K+-pump fluxes in rat erythrocytes and mouse macrophages was less sensitive to genins than to the corresponding cardiac glycosides. 4. Dihydroouabain was 3, 10 and 75 times less active than ouabain in inhibiting the initial rate of Na+, K+-pump fluxes in human and rat erythrocytes and in mouse macrophages respectively. 5. In conclusion, Na+, K+-pump fluxes measured under initial rate conditions in human erythrocytes exhibit an unusually high sensitivity to genins of cardiac glycosides. This property probably results from the fast binding rate constants of genins and the slow association rates of glycosides to human red cells. PMID:3390651

  16. Determination of the triterpene glycosides in sea cucumbers by liquid chromatography with evaporative light scattering and mass spectrometry detection.

    PubMed

    Yang, Jie; Wang, Yuanhong; Zhang, Ran; Jiang, Tifngfu; Lv, Zhihua

    2015-04-01

    Holothurian triterpene glycosides possess various kinds of biological activities, including antifungal, cytotoxic, hemolytic, cytostatic, and immunomodulatory effects. In this study, a rapid extraction method of triterpene glycosides from sea cucumbers using a small column of C18 solid phase was first developed. Furthermore, a novel high-performance liquid chromatography method coupled with evaporative light scattering detection and electrospray ionization mass spectrometry was established for the determination of each triterpene glycosides from different sea cucumbers. Simultaneous separation of all kind of triterpene glycoside were achieved on a C18 column. A gradient of aqueous acetonitrile was applied, and the method was validated. The liquid chromatography method was applied to the online mass detection to identify the triterpene glycosides in the purified extraction of eight kinds of pulverized sea cucumber from the market of Qingdao, China. The negative mode of [M-H](-)/[M-Na](-) exclusively shown signals corresponding to the triterpene glycosides previously reported and the MS(2) product ions of those ions indicate the specific structure of each triterpene glycoside. PMID:25604752

  17. Phenylethanoid glycosides in tepals of Magnolia salicifolia and their occurrence in flowers of Magnoliaceae.

    PubMed

    Porter, Elaine A; Kite, Geoffrey C; Veitch, Nigel C; Geoghegan, Ivey A; Larsson, Sonny; Simmonds, Monique S J

    2015-09-01

    Phenylethanoid glycosides were among the major UV-absorbing components in 80% aq. CH3OH extracts of the tepals of Magnolia salicifolia (Siebold & Zucc.) Maxim. (Magnoliaceae; Magnolia subgenus Yulania). Structural characterisation of isolated compounds by spectroscopic and chemical methods revealed three previously unrecorded examples, yulanoside A, yulanoside B and 2'-rhamnoechinacoside, and the known compounds echinacoside and crassifolioside; chromatographic methods also identified verbascoside in the tepal extract. Yulanoside A is the first reported example of a phenylethanoid pentaglycoside, namely hydroxytyrosol 1-O-{?-D-glucopyranosyl-(1?4)-?-D-glucopyranosyl-(1?6)-[3,4-dihydroxycinnamoyl-(?4)][?-L-rhamnopyranosyl-(1?3)][?-L-rhamnopyranosyl-(1?2)]-?-D-glucopyranoside}. A survey of Magnolia sensu lato and Liriodendron (the two genera of Magnoliaceae) suggested that yulanoside A and its deglucosyl derivative (yulanoside B) were a feature of the tepal chemistry of Magnolia subgenus Yulania (except Magnolia acuminata, the sole member of section Tulipastrum, which did not accumulate phenylethanoid glycosides). The two species of Liriodendron and examined examples of Magnolia subgenus Magnolia sections Magnolia and Rytidospermum (subsection Oyama) also accumulated phenylethanoid glycosides in their tepals and in these species, and in subgenus Yulania, the major compounds were one or more of echinacoside, 2'-rhamnoechinacoside, crassifolioside and verbascoside. Levels of phenylethanoid glycosides were found to be much lower in species studied from Magnolia sections Gwillimia, Macrophylla and Rytidospermum (subsection Rytidospermum), although yulanoside A was detectable in M. macrophylla and this may have some bearing on the placement of section Macrophylla, which is currently uncertain. In the isolates of yulanoside B and echinacoside, minor phenylethanoid glycosides were determined to be analogues of these compounds with ?-D-xylose at C-3' of the primary glucose rather than ?-L-rhamnose. PMID:26093323

  18. Colochirosides B1, B2, B3 and C, Novel Sulfated Triterpene Glycosides from the Sea Cucumber Colochirus robustus (Cucumariidae, Dendrochirotida).

    PubMed

    Silchenko, Alexandra S; Kalinovsky, Anatoly I; Avilov, Sergey A; Andryjaschenko, Pelageya V; Dmitrenok, Pavel S; Kalinin, Vladimir I; Yurchenko, Ekaterina A; Dolmatov, Igor Yu

    2015-10-01

    Four new triterpene glycosides, colochirosides B1 (1), B2 (2), B3 (3) and C (4) have been isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). Six known earlier glycosides from representatives of two families of the order Dendrochirotida have also been found in C. robustus. Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass spectrometry. All the glycosides belong to the holostane series and contain tetrasaccharide linear carbohydrate chains with one or two sulfate groups. Cytotoxic activities of glycosides 1-4 against the ascite form of mouse Ehrlich carcinoma cells and hemolytic activities against mouse erythrocytes have been studied. Hemolytic activity of the glycosides was higher than cytotoxic. Glycosides 3 and 4 demonstrated strong effects, whereas compounds 1 and 2 containing the hydroxy-group in the side chains showed moderate hemolytic activity and were not cytotoxic. PMID:26669103

  19. Quantum reverse hypercontractivity

    NASA Astrophysics Data System (ADS)

    Cubitt, Toby; Kastoryano, Michael; Montanaro, Ashley; Temme, Kristan

    2015-10-01

    We develop reverse versions of hypercontractive inequalities for quantum channels. By generalizing classical techniques, we prove a reverse hypercontractive inequality for tensor products of qubit depolarizing channels. We apply this to obtain a rapid mixing result for depolarizing noise applied to large subspaces and to prove bounds on a quantum generalization of non-interactive correlation distillation.

  20. Reversible Shape Memory

    NASA Astrophysics Data System (ADS)

    Zhou, Jing; Li, Qiaoxi; Turner, Sara; Brosnan, Sarah; Tippets, Cary; Carrillo, Jan-Michael; Nykypnachuk, Dmytro; Gang, Oleg; Dobrynin, Andrey; Lopez, Rene; Ashby, Valerie; Sheiko, Sergei

    2014-03-01

    Reversible shape memory has been achieved on various shapes, e.g. hairpin, origami, coil, robotic gripper and flow rate control device, allowing for multiple switching between encoded shapes without applying any external force. Also, the reversible photonic structure molded in dielectric elastomers has been designed. Maximum reversibility can be achieved by tuning the crosslinking density and the degree of crystallinity of semi-crystalline elastomers. Different crystallization protocols including isothermal and cooling crystallization have been applied to develop a universal picture integrating different shape memory (SM) behaviors: conventional one-way SM, two-way reversible SM, and one-way reversible SM. Acknowledge financial support from the NSF DMR-1122483, DMR- 1004576, and DMR-1206957.

  1. β-Hydroxydihydrochalcone and flavonoid glycosides along with triterpene saponin and sesquiterpene from the herbs of Pimpinella rhodantha Boiss.

    PubMed

    Özbek, Hilal; Güvenalp, Zühal; Kuruüzüm-Uz, Ay E; Kazaz, Cavit; Demirezer, L Ömür

    2016-04-01

    A new β-hydroxydihydrochalcone glycoside named ziganin (1) and a new acylated flavonol glycoside named isorhamnetin-3-O-α-L-(2″,3″-di-O-trans-coumaroyl)-rhamnopyranoside) (2), along with two known flavonoid glycosides, a β-hydroxydihydrochalcone glycoside, a hydroxybenzoic acid derivative, a trinorguaiane type sesquiterpenoid, a triterpenic saponin and a polyol were isolated from the herbs of Pimpinella rhodantha Boiss. Their structures were elucidated on the basis of spectroscopic analyses including 1D-and 2D-NMR, UV, IR, CD, ESI-MS, APCI-MS, HR-ESI-MS techniques. The isolated compounds were evaluated for their antioxidant capacity through the DPPH free-radical scavenging assay and ferrous ion-chelating power test. PMID:26207840

  2. Rapid analysis of the main components of the total glycosides of Ranunculus japonicus by UPLC/Q-TOF-MS.

    PubMed

    Rui, Wen; Chen, Hongyuan; Tan, Yuzhi; Zhong, Yanmei; Feng, Yifan

    2010-05-01

    A rapid method for the analysis of the main components of the total glycosides of Ranunculus japonicus (TGOR) was developed using ultra-performance liquid chromatography with quadrupole-time-of-flight mass spectrometry (UPLC/Q-TOF-MS). The separation analysis was performed on a Waters Acquity UPLC system and the accurate mass of molecules and their fragment ions were determined by Q-TOF MS. Twenty compounds, including lactone glycosides, flavonoid glycosides and flavonoid aglycones, were identified and tentatively deduced on the basis of their elemental compositions, MS/MS data and relevant literature. The results demonstrated that lactone glycosides and flavonoids were the main constituents of TGOR. Furthermore, an effective and rapid pattern was established allowing for the comprehensive and systematic characterization of the complex samples. PMID:20521547

  3. Acid-Assisted Ball Milling of Cellulose as an Efficient Pretreatment Process for the Production of Butyl Glycosides.

    PubMed

    Boissou, Florent; Sayoud, Nassim; De Oliveira Vigier, Karine; Barakat, Abdellatif; Marinkovic, Sinisa; Estrine, Boris; Jrme, Franois

    2015-10-12

    Ball milling of cellulose in the presence of a catalytic amount of H2SO4 was found to be a promising pre-treatment process to produce butyl glycosides in high yields. Conversely to the case of water, n-butanol has only a slight effect on the recrystallization of ball-milled cellulose. As a result, thorough depolymerization of cellulose prior the glycosylation step is no longer required, which is a pivotal aspect with respect to energy consumption. This process was successfully transposed to wheat straw from which butyl glycosides and xylosides were produced in good yields. Butyl glycosides and xylosides are important chemicals as they can be used as hydrotropes but also as intermediates in the production of valuable amphiphilic alkyl glycosides. PMID:26346950

  4. Reverse Engineering and CAE

    NASA Astrophysics Data System (ADS)

    Endo, Masashi

    Existing CAE is based on CAD data and is mainly applied to design and development. Product-based CAE to acquire data from actual products and implement CAE based on the derived data is being actively studied now. The present paper describes the important points in using reverse engineering that acquires data using noncontact 3D measuring instruments and generates CAD and CAE models based on the derived data. The present paper furthermore introduces the uniquely developed automatic surfacing tool, Clay Galaxy, for use in reverse engineering. The effectiveness of reverse engineering and Product-based CAE is also explained.

  5. Pharmacokinetics, tissue distribution and excretion study of a furostanol glycoside-based standardized fenugreek seed extract in rats.

    PubMed

    Kandhare, Amit D; Bodhankar, Subhash L; Mohan, V; Thakurdesai, Prasad A

    2015-08-01

    The furostanol glycoside isolated from the seed of fenugreek (SFSE-G) has an array of pharmacological activities. To date, no validated high-performance liquid chromatography (HPLC) method has been reported for quantification of SFSE-G in biological samples. Hence, the aim of the present study was to study the pharmacokinetics, tissue distribution and excretion profiles of SFSE-G after oral administration in rats. A rapid, sensitive, selective, robust and reproducible HPLC method has been developed for determination of SFSE-G in the rat biological samples. The chromatographic separation was accomplished on a reversed-phase C18 column using formic acid and acetonitrile (80:20) as mobile phase at a flow rate of 1.0?mL/min and 274?nm as a detection wavelength. The assay was linear for SFSE-G with the correlation coefficients (R(2)) >0.996. The analytes were stable during samples storage and handling, and no matrix effects were observed. After oral dosing of SFSE-G at a dose of 200?mg/kg, the elimination half-life was app. 40.10?h. It showed relatively slowly distribution and eliminated in urine and feces after 24?h, and could be detected until 108?h post-dosing. Following oral single dose (200?mg/kg), SFSE-G was detected in lung and brain which indicated that it could cross the blood-brain barrier. It is a major route of elimination is excretion through urine and feces. In conclusion, oral administration of SFSE-G showed slow distribution to tissues, such as lung and brain, but showed fast renal elimination. PMID:26104039

  6. Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

    NASA Astrophysics Data System (ADS)

    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.

  7. Antihyperglycemic activity of phenylpropanoyl esters of catechol glycoside and its dimers from Dodecadenia grandiflora.

    PubMed

    Kumar, Manmeet; Rawat, Preeti; Rahuja, Neha; Srivastava, Arvind Kumar; Maurya, Rakesh

    2009-01-01

    Bioactivity-guided separation of an antihyperglycemic extract from the leaves of Dodecadenia grandiflora afforded two phenylpropanoyl esters of catechol glycosides (1 and 4) and two lignane bis(catecol glycoside)esters (2 and 3). Their structures were established on the basis of extensive spectroscopic analysis (1D and 2D-NMR, MS). Compounds 2 and 3 are believed to be derived from dimerization via the two phenylpropanoid units of 1. Compounds 1-4 showed significant antihyperglycemic activity in streptozotocin-induced (STZ) diabetic rats, which is comparable to the standard drug metformin. Our results provide support to explain the use of D. grandiflora as antihyperglycemic agent by the traditional medical practitioners. PMID:19700178

  8. Bacteroides thetaiotaomicron VPI-5482 glycoside hydrolase family 66 homolog catalyzes dextranolytic and cyclization reactions.

    PubMed

    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. PMID:22776355

  9. Two new quercetin glycoside derivatives from the fruits of Gardenia jasminoides var. radicans.

    PubMed

    Yu, Shaofu; Fu, Shuna; Liu, Bailian; Zhang, Ying; Zhou, Guangxiong

    2015-01-01

    Two new quercetin glycoside derivatives named quercetin-3-O-[2-O-trans-caffeoyl-?-L-rhamnopyranosyl-(1 ? 6)-?-D-glucopyranoside] (1) and quercetin-3-O-[2-O-trans-caffeoyl-?-L-rhamnopyranosyl-(1 ? 6)-?-D-glucopyranoside] (2) along with three known flavonoids, 5-hydroxy-6,7,3',4',5'-pentamethoxyflavone (3), 5,7-dihydroxy-8-methoxyflavone (4) and kaempferol 3-O-?-D-glucopyranoside (5), were isolated from the fruits of Gardenia jasminoides var. radicans. The structures of the new compounds were determined by means of extensive spectroscopic analysis (1D, 2D NMR and HR-ESI-MS), glycoside hydrolysis and sugar HPLC analysis after derivatisation. This is the first report on the isolation of a pair of compounds with ? or ?-L-rhamnopyranosyl configuration from plant and the first detail assignment of their NMR data. PMID:25656831

  10. Pulse radiolysis study of daunorubicin redox reactions: redox cycles or glycosidic cleavage

    SciTech Connect

    Houee-Levin, C.; Gardes-Albert, M.; Ferradini, C.

    1986-01-01

    Two aspects of daunorubicin reactivity were investigated by pulse radiolysis. The reactions of O/sub 2/ and O/sub 2/- with the semiquinone and the hydroquinone transients of daunorubicin were determined and their rate constants measured. Although O/sub 2/- can reduce the drug and its semiquinone form, it is a more powerful oxidant towards the two reduced transients. The hydroquinone daunorubicin glycosidic cleavage in aqueous solution was studied. Three intermediates were seen and characterized by their absorption spectra, their formation and decay kinetics. The competition between these two main processes was evaluated in the conditions of pulse radiolysis. Even under low O/sub 2/ partial pressures the redox cycles are much more rapid than the glycosidic cleavage and a relatively high O/sub 2/- steady state is settled. Biological implications are discussed.

  11. BACE1 (beta-secretase) inhibitory chromone glycosides from Aloe vera and Aloe nobilis.

    PubMed

    Lv, Liang; Yang, Qing-Yun; Zhao, Ying; Yao, Chun-Suo; Sun, Yang; Yang, Eun-Ju; Song, Kyung-Sik; Mook-Jung, Inhee; Fang, Wei-Shuo

    2008-04-01

    Four new chromone glycosides allo-aloeresin D (2) , C-2'-decoumaroyl-aloeresin G (8), 2'-O-coumaroyl-(S)-aloesinol (9), 2'-O-[ P-methoxy-(E)-cinnamoyl]-(S)-aloesinol (10) and nine known chromone glycosides ( 1, 3 - 7, 11 - 13) were isolated from two Aloe spp. plants, A. vera and A. nobilis. Among them, 1 and 8 showed significant inhibitory activity against BACE1 (beta-secretase) with IC (50) values of 39.0 and 20.5 x 10 (-6) M, as well as inhibition of Abeta (1-42) production by 7.4 and 12.3 %, respectively, in B103 neuroblastoma cells at 30 ppm. The preliminary structure-activity relationships of ALOE chromone glucosides were also discussed. PMID:18543151

  12. Acyclic congeners from Actinoalloteichus cyanogriseus provide insights into cyclic bipyridine glycoside formation.

    PubMed

    Fu, Peng; Zhu, Yiguang; Mei, Xiangui; Wang, Yi; Jia, Haijian; Zhang, Changsheng; Zhu, Weiming

    2014-08-15

    Inactivation of the O-methyltransferase gene crmM of Actinoalloteichus cyanogriseus WH1-2216-6 led to a mutant that produced three new acyclic bipyridine glycosides, cyanogrisides E-G (1-3). Further chemical analysis of the wild strain yielded 1 and another new analogue, cyanogriside H (4). Compounds 1-4 possess a skeleton consisting of a 2,2'-bipyridine and a d-quinovose or l-rhamnose sugar moiety. Cyanogriside G (3) was considered to be a key biosynthetic intermediate of the cyclic bipyridine glycosides cyanogrisides A-D. Compounds 2 and 3 showed cytotoxicities against HCT116 and HL-60 cells, and compounds 1 and 4 were cytotoxic on K562 cells. PMID:25090585

  13. New antibacterial isocoumarin glycosides from a wetland soil derived fungal strain Metarhizium anisopliae.

    PubMed

    Tian, Jie-Feng; Li, Peng-Ju; Li, Xiao-Xia; Sun, Ping-Hua; Gao, Hao; Liu, Xing-Zhong; Huang, Peng; Tang, Jin-Shan; Yao, Xin-Sheng

    2016-03-01

    Eight new isocoumarin glycosides (1-8) were obtained from the solid culture of the wetland soil-derived fungus Metarhizium anisopliae (No. DTH12-10). Their chemical structures were elucidated by analyses of HR ESI-TOF MS, (1)H, (13)C NMR, (1)H-(1)H COSY, HSQC, and HMBC spectra. The absolute configurations were determined by single crystal X-ray diffraction, circular dichroism (CD) spectrum, and chemical derivatization methods. In addition, inhibition of the biofilm formation and the secretion of virulence factor of the new isocoumarin glycosides against Pseudomonas aeruginosa strain PAOA (clinical isolates) were evaluated. The result revealed that compound 1 showed antibacterial activity comparable with (Z)-4-bromo-5-(bromomethylene)-2(5H)-furanone (BF). PMID:26848110

  14. Effect of Blueberry Anthocyanins Malvidin and Glycosides on the Antioxidant Properties in Endothelial Cells

    PubMed Central

    Huang, Wuyang; Zhu, Yunming; Li, Chunyang

    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.

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

    PubMed

    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. PMID:11830167

  16. Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

    PubMed Central

    Park, Joo-In; Bae, Hae-Rahn; Kim, Chang Gun; Stonik, Valentin A.; Kwak, Jong-Young

    2014-01-01

    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. PMID:25250309

  17. Hydrolysis of glycosidically bound flavour compounds from oak wood by Oenococcus oeni.

    PubMed

    Bloem, Audrey; Lonvaud-Funel, Aline; de Revel, Gilles

    2008-02-01

    Malolactic fermentation (MLF), which is conducted by lactic acid bacteria (LAB), has a significant influence on the stability and organoleptic quality of wine. Recent studies have shown that when MLF is carried out in oak wood barrels, LAB were also able to interact with wood and increase volatile compound contents such as vanillin during MLF. The release of these compounds indicates that LAB may convert vanillin precursors present in oak wood. In this work, the effect of commercial glycosidases on the released vanillin was firstly studied. This aldehyde is present in wood extracts in monoglycosidic forms where the major glycones are arabinose and xylose. Other aglycons released during MLF in barrels, syringaldehyde and whisky-lactones, can be considered as other sources of aroma. Secondly, strains selected with high activities toward glycoside substrates could hydrolyse vanillin glycoside precursors from oak wood with the same efficiency as commercial enzymes. PMID:17993382

  18. Synthesis and Characterization of Hapten-Protein Conjugates for Antibody Production against Cyanogenic Glycosides.

    PubMed

    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. PMID:26197297

  19. Isoform-specific Stimulation of Cardiac Na/K Pumps by Nanomolar Concentrations of Glycosides

    PubMed Central

    Gao, Junyuan; Wymore, Randy S.; Wang, Yongli; Gaudette, Glenn R.; Krukenkamp, Irvin B.; Cohen, Ira S.; Mathias, Richard T.

    2002-01-01

    It is well-known that micromolar to millimolar concentrations of cardiac glycosides inhibit Na/K pump activity, however, some early reports suggested nanomolar concentrations of these glycosides stimulate activity. These early reports were based on indirect measurements in multicellular preparations, hence, there was some uncertainty whether ion accumulation/depletion rather than pump stimulation caused the observations. Here, we utilize the whole-cell patch-clamp technique on isolated cardiac myocytes to directly measure Na/K pump current (IP) in conditions that minimize the possibility of ion accumulation/depletion causing the observed effects. In guinea pig ventricular myocytes, nanomolar concentrations of dihydro-ouabain (DHO) caused an outward current that appeared to be due to stimulation of IP because of the following: (1) it was absent in 0 mM [K+]o, as was IP; (2) it was absent in 0 mM [Na+]i, as was IP; (3) at reduced [Na+]i, the outward current was reduced in proportion to the reduction in IP; (4) it was eliminated by intracellular vanadate, as was IP. Our previous work suggested guinea pig ventricular myocytes coexpress the α1- and α2-isoforms of the Na/K pumps. The stimulation of IP appears to be through stimulation of the high glycoside affinity α2-isoform and not the α1-isoform because of the following: (1) regulatory signals that specifically increased activity of the α2-isoform increased the amplitude of the stimulation; (2) regulatory signals that specifically altered the activity of the α1-isoform did not affect the stimulation; (3) changes in [K+]o that affected activity of the α1-isoform, but not the α2-isoform, did not affect the stimulation; (4) myocytes from one group of guinea pigs expressed the α1-isoform but not the α2-isoform, and these myocytes did not show the stimulation. At 10 nM DHO, total IP increased by 35 ± 10% (mean ± SD, n = 18). If one accepts the hypothesis that this increase is due to stimulation of just the α2-isoform, then activity of the α2-isoform increased by 107 ± 30%. In the guinea pig myocytes, nanomolar ouabain as well as DHO stimulated the α2-isoform, but both the stimulatory and inhibitory concentrations of ouabain were ∼10-fold lower than those for DHO. Stimulation of IP by nanomolar DHO was observed in canine atrial and ventricular myocytes, which express the α1- and α3-isoforms of the Na/K pumps, suggesting the other high glycoside affinity isoform (the α3-isoform) also was stimulated by nanomolar concentrations of DHO. Human atrial and ventricular myocytes express all three isoforms, but isoform affinity for glycosides is too similar to separate their activity. Nevertheless, nanomolar DHO caused a stimulation of IP that was very similar to that seen in other species. Thus, in all species studied, nanomolar DHO caused stimulation of IP, and where the contributions of the high glycoside affinity α2- and α3-isoforms could be separated from that of the α1-isoform, it was only the high glycoside affinity isoform that was stimulated. These observations support early reports that nanomolar concentrations of glycosides stimulate Na/K pump activity, and suggest a novel mechanism of isoform-specific regulation of IP in heart by nanomolar concentrations of endogenous ouabain-like molecules. PMID:11929882

  20. Anti-inflammatory properties of a triterpenoidal glycoside from Momordica cochinchinensis in LPS-stimulated macrophages.

    PubMed

    Jung, Kiwon; Chin, Young-Won; Yoon, Kee dong; Chae, Hee-Sung; Kim, Chul Young; Yoo, Hunseung; Kim, Jinwoong

    2013-02-01

    Two triterpenoidal saponins were isolated from the seeds of Momordica cochinchinensis Sprenger (Cucurbitaceae). Identification of chemical structures has been performed by (1)H- and (13)C-NMR spectroscopy and gas chromatography (GC). One of the saponins is a new gypsogenin glycoside, named as gypsogenin 3-O-β-D-galactopyranosyl(1→2)-[α-L-rhamnopyranosyl(1→3)]-β-D-glucuronopyranoside (compound 1), which is reported for the first time from natural resources. The other saponin is a quillaic acid glycoside (compound 2), which showed anti-inflammatory activities in RAW 264.7 cells. The mechanistic understanding of anti-inflammatory activities demonstrates that compound 2 inhibits lipopolysaccharide-induced expression of nitric oxide and IL-6 via NF-κB pathway. PMID:22916793

  1. New Acylated Flavonol Glycosides and a Phenolic Profile of Pritzelago alpina, a Forgotten Edible Alpine Plant.

    PubMed

    Corradi, Elisabetta; De Mieri, Maria; Cadisch, Larissa; Abbet, Christian; Hamburger, Matthias; Potterat, Olivier

    2016-02-01

    Thirteen acylated flavonoid glycosides, 1-13, including eleven new congeners, 3-13, were isolated from the aerial parts of Pritzelago alpina (Brassicaceae) by a combination of column chromatography on Sephadex LH-20, and preparative and semi-preparative HPLC. The structures were established by extensive NMR and MS experiments in combination with acid hydrolysis and sugar analysis by GC/MS. The new compounds were shown to be kaempferol and quercetin glycosides acylated for most of them by a branched short chain fatty acid or a hydroxycinnamic acid residue on the sugar portion. As shown by a HPLC-DAD analysis of a MeOH extract, these compounds are the main phenolic constituents in the aerial parts of the plant. PMID:26880431

  2. Mycotoxins and cyanogenic glycosides in staple foods of three indigenous people of the Colombian Amazon.

    PubMed

    Diaz, Gonzalo J; Krska, Rudolf; Sulyok, Michael

    2015-12-01

    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. PMID:26391446

  3. A new triterpenoid glycoside from the leaves and stems of Duranta repens.

    PubMed

    Furusawa, Chisato; Yasuda, Shin; Tsuji, Hiroshi; Ito, Show; Miyashita, Hiroyuki; Yoshimitsu, Hitoshi; Nohara, Toshihiro; Ono, Masateru

    2016-01-01

    A new triterpenoid glycoside (1) was isolated from the methanol extract of the leaves and stems of Duranta repens L. (Verbenaceae) along with 14 known compounds consisting of eight triterpenoids, four iridoids, one phenylethanoid glycoside and one flavonoid. The chemical structure of 1 was determined to be bayogenin 3-O-[?-D-glucopyranoside]-28-O-[?-L-rhamnopyranosyl-(1?5)-O-?-D-apiofuranosyl-(1?4)-O-?-L-rhamnopyranosyl-(1?2)-O-?-L-arabinopyranosyl] ester, based on spectroscopic data. In addition, the inhibitory effects of the isolates on lipoxygenase activity were examined. Among them, acteoside and apigenin resulted in 943.6% and 824.7% inhibition, respectively, at 0.5mM. PMID:26134247

  4. Synthesis of thymol glycosides under SCCO2 conditions using amyloglucosidase from Rhizopus mold.

    PubMed

    Kumar, Tiruppur Venkatachallam Suresh; Sankar, Kadimi-Udaya; Divakar, Soundar

    2013-08-01

    Enzymatic synthesis of water soluble thymol glycosides were carried out using amyloglucosidase from Rhizopus mold under supercritical carbon dioxide (SCCO2) conditions of 120 bar pressure at 50 °C. Thymol 1 formed glycosides with D-galactose 2, D-mannose 3, D-fructose 4, D-ribose 5 and D-arabinose 6 in yields ranging from 20.6% to 54.2%. Spectral characterization studies revealed that the reaction occurred between the phenolic OH group of thymol and 1-O/2-O groups of D-fructose and C-1 group of D-galactose, D-mannose, D-ribose and D-arabinose resulting in monoglycosylated/arylated derivatives. PMID:24425985

  5. Induction of apoptosis in colon cancer cells treated with isorhamnetin glycosides from Opuntia ficus-indica pads.

    PubMed

    Antunes-Ricardo, Marilena; Moreno-Garca, Beatriz E; Gutirrez-Uribe, Janet A; Ariz-Hernndez, 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 ?g/mL) and against Caco2 (8.2??0.3 ?g/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. PMID:25186940

  6. Pregnane Glycosides Interfere With Steroidogenic Enzymes to Down-Regulate Corticosteroid Production in Human Adrenocortical H295R Cells

    PubMed Central

    KOMARNYTSKY, SLAVKO; ESPOSITO, DEBORA; POULEV, ALEXANDER; RASKIN, ILYA

    2013-01-01

    A group of bioactive steroidal glycosides (pregnanes) with anorectic activity in animals was isolated from several genera of milkweeds including Hoodia and Asclepias. In this study, we investigated the effects, structure-activity relationships, and mechanism of action of pregnane glycosides on steroidogenesis in human adrenocortical H295R cells. Administration of pregnane glycosides for 24 h suppressed the basal and forskolin-stimulated release of androstenedione, corticosterone, and cortisone from H295R cells. The conversion of progesterone to 11-deoxycorticosterone and 17-hydroxyprogesterone to either androstenedione or 11-deoxycortisol was most strongly affected, with 12-cinnamoyl-, benzoyl-, and tigloyl-containing pregnanes showing the highest activity. Incubation of pregnane glycosides for 24 h had no effect on mRNA transcripts of CYP11A1, CYP21A1, CYP11B1 cytochrome enzymes and steroidogenic acute regulatory protein (StaR) protein, yet resulted in twofold decrease in HSD3B1 mRNA levels. At the same time, pregnane glycosides had no effect on the CYP1, 2, or 3 drug and steroid metabolism enzymes and showed weak Na+/K+ ATPase and glucocorticoid receptor binding. Taken together, these data suggest that pregnane glycosides specifically suppress steroidogenesis through strong inhibition of 11β-hydroxylase and steroid 17-alpha-monooxygenase, and weak inhibition of cytochrome P450 side chain cleavage enzyme and 21β-hydroxylase, but not 3β-hydroxysteroid dehydrogenase/isomerase. PMID:23065845

  7. Energy by reverse electrodialysis

    NASA Astrophysics Data System (ADS)

    Lacey, R. E.

    The use of reverse electrodialysis, a reverse desalinization process, to derive energy from the difference between the chemical potentials of concentrated and dilute salt solutions is evaluated. The process employs the flows of brine and dilute solutions through alternating cells bounded by cation- and anion-exchange membranes in a stack placed between two electrodes to generate a voltage by the passage of salt through the membranes. Potential sources of brine include the salt domes of oil and gas wells, salt water lakes, and geothermal brines. Experiments have shown the technical feasibility of reverse electrodialysis, and have confirmed equations derived to predict their performance. Calculations show that in order for reverse electrolysis to be economically attractive, the internal resistance of the cells should be minimized and net output power maximized by using large concentration ratios between the brine and the dilute solution, the minimum dilute compartment and diffusive boundary layer thicknesses, low-resistance, highly selective membranes and appropriate manufacturing methods.

  8. Reversion of streptococcal protoplasts.

    PubMed

    Bibel, D J; Lawson, J W

    1972-10-01

    The reversion of protoplasts of Streptococcus faecium was examined by light and scanning electron microscopy. Regularly shaped streptococci emerged from the narrow region of large, oval protoplasts. PMID:5079076

  9. Reversing the arms race

    SciTech Connect

    von Hippel, F. ); Sagdeev, R.Z. )

    1992-01-01

    This paper contains proceedings of Reversing The Arms Race. Topics covered include: Verifying Reductions of Nuclear Warheads; Verifying Limits on Nuclear-Armed Cruise Missiles; and The Technical Basis for Warhead Detection.

  10. Reversible shape memory

    NASA Astrophysics Data System (ADS)

    Sheiko, Sergei; Zhou, Jing; White, Sarah; Ashby, Valerie

    2012-02-01

    An ``Achilles' heel'' of shape memory materials is that shape transformations triggered by an external stimulus are usually irreversible. Here we present a new concept of reversible transitions between two well-defined shapes by controlling hierarchic crystallization of a dual-network elastomer. The reversibility was demonstrated for different types of shape transformations including rod bending, winding of a helical coil, and widening an aperture. The distinct feature of the reversible shape alterations is that both counter-shapes are infinitely stable at a temperature of exploitation. Shape reversibility is highly desirable property in many practical applications such as non-surgical removal of a previously inserted catheter and handfree wrapping up of an earlier unraveled solar sail on a space shuttle.

  11. Inhibitory activity against urease of quercetin glycosides isolated from Allium cepa and Psidium guajava.

    PubMed

    Shabana, Samah; Kawai, Azusa; Kai, Kenji; Akiyama, Kohki; Hayashi, Hideo

    2010-01-01

    Methanolic extracts of edible plants and seaweeds were tested for their inhibitory activity against Jack bean urease. Quercetin-4'-O-beta-D-glucopyranoside was isolated from Allium cepa as a urease inhibitor with an IC(50) value of 190 microM-. Quercetin and two quercetin glycosides, avicularin and guaijaverin, were isolated from Psidium guajava as urease inhibitors with respective IC(50) values of 80 microM-, 140 microM-, and 120 microM-. PMID:20378972

  12. A new glucuronolactone glycoside phoenixoside B from the seeds of Phoenix dactylifera.

    PubMed

    Azmat, Sumbul; Ifzal, Rehana; Mohammad, Faryal Vali; Ahmad, Viqar Uddin; Zahoor, Aqib

    2013-09-01

    A new glucuronolactone glycoside, phoenixoside B (1), has been isolated from the n-butanol soluble fraction of seeds of Phoenix dactylifera. The structure was characterized as 1-(1'-ethyl-beta-D-glucosyl)-4,5-diethyl-[alpha-D-glucofuranourono-6,3-lactone] on the basis of 1D and 2D-NMR spectroscopy and high-resolution mass spectrometry. PMID:24273868

  13. [Flavone C-glycosides from seeds of Ziziphus jujuba var. spinosa].

    PubMed

    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. PMID:26281588

  14. Methylenebisnicotiflorin: a rare methylene-bridged bisflavonoid glycoside from ripe Pu-er tea.

    PubMed

    Tao, Mu-Ke; Xu, Min; Zhang, Han; Chen, Hui; Liu, Chang; Zhu, Hong-Tao; Wang, Dong; Yang, Chong-Ren; Zhang, Ying-Jun

    2016-04-01

    A new methylene-bridged dimeric flavonol glycoside, methylenebisnicotiflorin (1), was isolated from ripe Pu-er tea, along with 10 known flavonoids (2-11) and seven known phenolic compounds (12-18). The structure elucidation was based on spectroscopic analysis. Among them, 1,3-dihydroxyphenyl-2-O-sulfate (13), 2,3,4-trihydroxybenzoic acid (16) and 3,3',4,4'-tetrahydroxybiphenyl (18) are reported from tea plants for the first time. PMID:26273895

  15. Palladium-catalyzed glycosylation: novel synthetic approach to diverse N-heterocyclic glycosides.

    PubMed

    Ji, Li; Xiang, Shao-Hua; Leng, Wei-Lin; Hoang, Kim Le Mai; Liu, Xue-Wei

    2015-03-20

    An efficient and highly stereoselective method for the construction of N-heterocyclic glycosides is reported. This method is based on a palladium-catalyzed allylation which proceeded to provide N-heterocyclic glycosyl compounds in good-to-excellent yields with ?- or ?-selectivity. Various N-nucleophiles were examined for this reaction and selected N-glycosyl isatin substrates were further elaborated to bis-indole sugars which have potential as antiproliferative drugs. PMID:25730324

  16. Two new phenylpropanoid glycosides with interesterification from Scrophularia dentata Royle ex Benth

    NASA Astrophysics Data System (ADS)

    Zhang, Liuqiang; Yang, Zhuo; Jia, Qi; Dorje, Gaawe; Zhao, Zhili; Guo, Fujiang; Li, Yiming

    2013-10-01

    Two new phenylpropanoid glycosides (1-2), along with seven known ones (3-9), were isolated from the whole plant of Scrophularia dentata Royle ex Benth. Their structures were elucidated by spectroscopic methods. Among them, compounds 1 and 2 failed to separated, because they can easily transform into each other by acyl migrant reaction. In this paper, the interesterification mechanism was discussed firstly and the rule can be used in the similar structure elucidation in future.

  17. New cytotoxic triterpene glycoside from the East China Sea cucumber Holothuria nobilis.

    PubMed

    Zhang, Jia-Jia; Zhu, Qi-Ke; Wu, Jun; Zhang, Hui-Wen

    2015-02-01

    A new cytotoxic triterpene glycoside named nobiliside E (1) has been obtained from the East China Sea cucumber Holothuria nobilis Selenka. Its structure was determined on the basis of NMR spectroscopic and MS analyses, together with chemical evidence. The new compound showed significant cytotoxicity to eight human tumor cell lines with IC50 values in the range of 0.53-4.06 ?g/mL. PMID:25920252

  18. Shamimin: a new flavonol C-glycoside from leaves of Bombax ceiba.

    PubMed

    Faizi, S; Ali, M

    1999-05-01

    Shamimin a new flavonol C-glycoside has been isolated as a pale yellow powder from the ethanolic extract of fresh, undried leaves of Bombax ceiba. Its structure has been elucidated as 2-(2,4,5-trihydroxyphenyl)-3,5,7-trihydroxy-6-C- glucopyranosyloxy-4H-1-benzopyran-4-one through extensive spectroscopic methods (IR, mass, 1H- and 13C-NMR), and 2D-NMR experiments. Shamimin showed antimicrobial activity against a few bacteria and fungi. PMID:10364851

  19. Production of Hesperetin Glycosides by Xanthomonas campestris and Cyclodextrin Glucanotransferase and Their Anti-allergic Activities

    PubMed Central

    Shimoda, Kei; Hamada, Hiroki

    2010-01-01

    The production of hesperetin glycosides was investigated using glycosylation with Xanthomonas campestris and cyclodextrin glucanotransferase (CGTase). X. campestris glucosylated hesperetin to its 3'-, 5-, and 7-O-glucosides, and CGTase converted hesperetin glucosides into the corresponding maltosides. The resulting 7-O-glucoside and 7-O-maltoside of hesperetin showed inhibitory effects on IgE antibody production and on O2- generation from rat neutrophils. PMID:22254014

  20. Reverse vending machine update

    SciTech Connect

    Rypins, S.; Papke, C.

    1986-02-01

    The document discusses reverse vending machines. Placed outdoors in supermarket parking lots or indoors in the lobby of the grocery market, these hightech machines exchange aluminum cans (or other containers in more specialized machines) for cash, coupons or redeemable receipts. The placement of reverse venders (RV) in or near supermarkets has made recycling more visible and more convenient, although the machines have yet to fully reach industry goals.

  1. Reversibility of antibiotic resistance

    PubMed Central

    2014-01-01

    Although theoretically attractive, the reversibility of resistance has proven difficult in practice, even though antibiotic resistance mechanisms induce a fitness cost to the bacterium. Associated resistance to other antibiotics and compensatory mutations seem to ameliorate the effect of antibiotic interventions in the community. In this paper the current understanding of the concepts of reversibility of antibiotic resistance and the interventions performed in hospitals and in the community are reviewed. PMID:24836051

  2. GH97 is a new family of glycoside hydrolases, which is related to the ?-galactosidase superfamily

    PubMed Central

    Naumoff, Daniil G

    2005-01-01

    Background As a rule, about 1% of genes in a given genome encode glycoside hydrolases and their homologues. On the basis of sequence similarity they have been grouped into more than ninety GH families during the last 15 years. The GH97 family has been established very recently and initially included only 18 bacterial proteins. However, the evolutionary relationship of the genes encoding proteins of this family remains unclear, as well as their distribution among main groups of the living organisms. Results The extensive search of the current databases allowed us to double the number of GH97 family proteins. Five subfamilies were distinguished on the basis of pairwise sequence comparison and phylogenetic analysis. Iterative sequence analysis revealed the relationship of the GH97 family with the GH27, GH31, and GH36 families of glycosidases, which belong to the ?-galactosidase superfamily, as well as a more distant relationship with some other glycosidase families (GH13 and GH20). Conclusion The results of this study show an unexpected sequence similarity of GH97 family proteins with glycoside hydrolases from several other families, that have (?/?)8-barrel fold of the catalytic domain and a retaining mechanism of the glycoside bond hydrolysis. These data suggest a common evolutionary origin of glycosidases representing different families and clans. PMID:16131397

  3. Sph3 Is a Glycoside Hydrolase Required for the Biosynthesis of Galactosaminogalactan in Aspergillus fumigatus.

    PubMed

    Bamford, Natalie C; Snarr, Brendan D; Gravelat, Fabrice N; Little, Dustin J; Lee, Mark J; Zacharias, Caitlin A; Chabot, Jose C; Geller, Alexander M; Baptista, Stefanie D; Baker, Perrin; Robinson, Howard; Howell, P Lynne; Sheppard, Donald C

    2015-11-13

    Aspergillus fumigatus is the most virulent species within the Aspergillus genus and causes invasive infections with high mortality rates. The exopolysaccharide galactosaminogalactan (GAG) contributes to the virulence of A. fumigatus. A co-regulated five-gene cluster has been identified and proposed to encode the proteins required for GAG biosynthesis. One of these genes, sph3, is predicted to encode a protein belonging to the spherulin 4 family, a protein family with no known function. Construction of an sph3-deficient mutant demonstrated that the gene is necessary for GAG production. To determine the role of Sph3 in GAG biosynthesis, we determined the structure of Aspergillus clavatus Sph3 to 1.25 . The structure revealed a (?/?)8 fold, with similarities to glycoside hydrolase families 18, 27, and 84. Recombinant Sph3 displayed hydrolytic activity against both purified and cell wall-associated GAG. Structural and sequence alignments identified three conserved acidic residues, Asp-166, Glu-167, and Glu-222, that are located within the putative active site groove. In vitro and in vivo mutagenesis analysis demonstrated that all three residues are important for activity. Variants of Asp-166 yielded the greatest decrease in activity suggesting a role in catalysis. This work shows that Sph3 is a glycoside hydrolase essential for GAG production and defines a new glycoside hydrolase family, GH135. PMID:26342082

  4. A male gift to its partner? Cyanogenic glycosides in the spermatophore of longwing butterflies (Heliconius)

    NASA Astrophysics Data System (ADS)

    Cardoso, Mrcio Zikn; Gilbert, Lawrence E.

    2007-01-01

    Males of several insect species transfer nuptial gifts to females during mating, typically in the form of a protein-rich spermatophore. In chemically defended species, males could potentially enhance such a gift with chemicals that help protect the female, her eggs, or both. This was shown for lepidopteran species that accumulate pyrrolizidine alkaloids. Most Heliconius butterflies are presumably protected from predators by virtue of de novo synthesized and/or sequestered cyanogenic glycosides. Males of Heliconius species are known to transfer nutritional gifts to the females but whether defensive chemicals could also be transferred is not known. To ascertain whether transfer of cyanogens occurs, we dissected freshly mated females from nine different Heliconius species and analyzed spermatophores for cyanogenic glycosides. We found cyanogens in the spermatophores of all nine species. This is the first time cyanogenic glycosides are reported in the spermatophores of arthropods. We discuss the implications of these findings for Heliconius biology and for other cyanogenic insects as well. We suggest that chemically defended species commonly lace their nuptial gifts with defensive chemicals to improve gift quality.

  5. Influence of Extraction Methods on the Yield of Steviol Glycosides and Antioxidants in Stevia rebaudiana Extracts.

    PubMed

    Periche, Angela; Castell, 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. PMID:25726419

  6. Zebrafish Chemical Screening Reveals the Impairment of Dopaminergic Neuronal Survival by Cardiac Glycosides

    PubMed Central

    Sun, Yaping; Dong, Zhiqiang; Khodabakhsh, Hadie; Chatterjee, Sandip; Guo, Su

    2012-01-01

    Parkinson's disease is a neurodegenerative disorder characterized by the prominent degeneration of dopaminergic (DA) neurons among other cell types. Here we report a first chemical screen of over 5,000 compounds in zebrafish, aimed at identifying small molecule modulators of DA neuron development or survival. We find that Neriifolin, a member of the cardiac glycoside family of compounds, impairs survival but not differentiation of both zebrafish and mammalian DA neurons. Cardiac glycosides are inhibitors of Na+/K+ ATPase activity and widely used for treating heart disorders. Our data suggest that Neriifolin impairs DA neuronal survival by targeting the neuronal enriched Na+/K+ ATPase α3 subunit (ATP1A3). Modulation of ionic homeostasis, knockdown of p53, or treatment with antioxidants protects DA neurons from Neriifolin-induced death. These results reveal a previously unknown effect of cardiac glycosides on DA neuronal survival and suggest that it is mediated through ATP1A3 inhibition, oxidative stress, and p53. They also elucidate potential approaches for counteracting the neurotoxicity of this valuable class of medications. PMID:22563390

  7. Strategies to reduce end-product inhibition in family 48 glycoside hydrolases.

    PubMed

    Chen, Mo; Bu, Lintao; Alahuhta, Markus; Brunecky, Roman; Xu, Qi; Lunin, Vladimir V; Brady, John W; Crowley, Michael F; Himmel, Michael E; Bomble, Yannick J

    2016-03-01

    Family 48 cellobiohydrolases are some of the most abundant glycoside hydrolases in nature. They are able to degrade cellulosic biomass and therefore serve as good enzyme candidates for biofuel production. Family 48 cellulases hydrolyze cellulose chains via a processive mechanism, and produce end products composed primarily of cellobiose as well as other cellooligomers (dp ≤ 4). The challenge of utilizing cellulases in biofuel production lies in their extremely slow turnover rate. A factor contributing to the low enzyme activity is suggested to be product binding to enzyme and the resulting performance inhibition. In this study, we quantitatively evaluated the product inhibitory effect of four family 48 glycoside hydrolases using molecular dynamics simulations and product expulsion free-energy calculations. We also suggested a series of single mutants of the four family 48 glycoside hydrolases with theoretically reduced level of product inhibition. The theoretical calculations provide a guide for future experimental studies designed to produce mutant cellulases with enhanced activity. Proteins 2016; 84:295-304. © 2016 Wiley Periodicals, Inc. PMID:26572060

  8. The Moraceae-based dart poisons of South America. Cardiac glycosides of Maquira and Naucleopsis species.

    PubMed

    Shrestha, T; Kopp, B; Bisset, N G

    1992-09-01

    The use of cardenolide-containing Moraceae in the dart poisons of South America is reviewed. Those prepared by the Chocó Indians of western Colombia--called niaará or kieratchi--have probably been made from the latex of Naucleopsis amara and N. glabra. In Ecuador, the Colorado Indians used N. chiguila, while the Coaiquer Indians still derive a poison from the latex of N. naga and the Cayapá Indians occasionally make use of a blowgun poison, hambi, which probably also comes from a Naucleopsis species. The Kaborí (Rio Uneiuxi Makú) Indians of north-western Brazil may have utilized Maquira coriacea, but a more recent collection documents N. mello-barretoi latex as a source of their poison. The Tikuna Indians of western Brazil included leaves and bark of N. stipularis in one of their poisons. The principal cardiac glycosides present in Maquira species are strophanthidin-based and the main ones occurring in Naucleopsis species are antiarigenin- as well as strophanthidin-based. The structures of two new glycosides, isolated from dart-poison samples, have been established as strophanthidin beta-D-glucomethylosido-D-alloside and beta-D-digitoxosido-D-alloside. The former is a major component of pakurin, the crystalline glycoside mixture prepared by Santesson in 1928 from a Chocó Indian poison. PMID:1434687

  9. Mechanoanions produced by mechanical fracture of bacterial cellulose: ionic nature of glycosidic linkage and electrostatic charging.

    PubMed

    Sakaguchi, Masato; Makino, Masakazu; Ohura, Takeshi; Iwata, Tadahisa

    2012-10-11

    Mechanoanions were produced by heterogeneous scission of the glycosidic linkages of the main chain of bacterial cellulose (BC); scission was induced by mechanical fracture of the BC in a vacuum in the dark at 77 K. The mechanoanions were detected using electron-spin-trapping methods with tetracyanoethylene. The yield of mechanoanions was positively correlated with the absolute value of the change in the Mulliken atomic charge, which was used as a descriptor of the ionic nature of the glycosidic linkage. Homogeneous scission of the glycosidic linkages induced by mechanical fracture generated mechanoradicals, the electron affinity of which was estimated on the basis of the energy of the lowest unoccupied molecular orbital for the model structure of the mechanoradical. It was concluded that the electrostatic charging of BC is caused by electron transfer from mechanoanions to mechanoradicals, which have high electron affinities. The electrostatic charge density of BC in a vacuum in the dark at 77 K was estimated to be 6.00 10(-1) C/g. PMID:22978760

  10. Transformation of cellulose into biodegradable alkyl glycosides by following two different chemical routes.

    PubMed

    Villandier, Nicolas; Corma, Avelino

    2011-04-18

    The transformation of cellulose into long-chain alkyl glycoside surfactants has been carried out following two different routes: (1) Direct transformation of cellulose to butyl-, hexyl-, octyl-, decyl- and dodecyl-α,β-glycosides in an ionic liquid media and Amberlyst-15Dry as catalysts, with mass yield of up to 82 %; and (2) two steps reaction with transformation of cellulose into methyl glucosides, with a procedure described by Zhang et al., followed by transacetalation with 1-octanol and 1-decanol in the presence of Amberlyst-15Dry. A kinetic study for the direct transformation of cellulose using 1-octanol has shown that depolymerisation of cellulose continues during the Fischer glycosidation. Increasing the chain length of the alcohol decreases the global reaction rate owing to an increase in the lipophilicity of the alcohol that decreases its contact with the carbohydrates. Finally, several acid catalysts were tested and the best results were obtained with Amberlyst-15Dry. PMID:21391304

  11. First Glycoside Hydrolase Family 2 Enzymes from Thermus antranikianii and Thermus brockianus with ?-Glucosidase Activity

    PubMed Central

    Schrder, Carola; Blank, Saskia; Antranikian, Garabed

    2015-01-01

    Two glycoside hydrolase encoding genes (tagh2 and tbgh2) were identified from different Thermus species using functional screening. Based on amino acid similarities, the enzymes were predicted to belong to glycoside hydrolase (GH) family 2. Surprisingly, both enzymes (TaGH2 and TbGH2) showed twofold higher activities for the hydrolysis of nitrophenol-linked ?-D-glucopyranoside than of -galactopyranoside. Specific activities of 3,966?U/mg for TaGH2 and 660?U/mg for TbGH2 were observed. In accordance, Km values for both enzymes were significantly lower when ?-D-glucopyranoside was used as substrate. Furthermore, TaGH2 was able to hydrolyze cellobiose. TaGH2 and TbGH2 exhibited highest activity at 95 and 90C at pH 6.5. Both enzymes were extremely thermostable and showed thermal activation up to 250% relative activity at temperatures of 50 and 60C. Especially, TaGH2 displayed high tolerance toward numerous metal ions (Cu2+, Co2+, Zn2+), which are known as glycoside hydrolase inhibitors. In this study, the first thermoactive GH family 2 enzymes with ?-glucosidase activity have been identified and characterized. The hydrolysis of cellobiose is a unique property of TaGH2 when compared to other enzymes of GH family 2. Our work contributes to a broader knowledge of substrate specificities in GH family 2. PMID:26090361

  12. Nickel-Catalyzed Proton-Deuterium Exchange (HDX) Procedures for Glycosidic Linkage Analysis of Complex Carbohydrates.

    PubMed

    Price, Neil P J; Hartman, Trina M; Vermillion, Karl E

    2015-07-21

    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 noncarbohydrate substituents. The glycosidic linkage positions are often determined by permethylation analysis, but this can be complicated by high viscosity or poor solubility, resulting in under-methylation. This is a drawback because an under-methylated position may be misinterpreted as the erroneous site of a linkage or substituent. Here, we describe an alternative approach to linkage analysis that makes use of a nonreversible deuterium exchange of C-H protons on the carbohydrate backbone. The exchange reaction is conducted in deuterated water catalyzed by Raney nickel, and results in the selective exchange of C-H protons adjacent to free hydroxyl groups. Hence, the position of the residual C-H protons is indicative of the position of glycosidic linkages or other substituents and can be readily assigned by heteronuclear single quantum coherence-nuclear magnetic resonance (HSQC-NMR) or, following suitable derivatization, by gas chromatography-mass spectroscopy (GC/MS) analysis. Moreover, because the only changes to the parent sugar are proton/deuterium exchanges, the composition and linkage analysis can be determined in a single step. PMID:26075577

  13. On thermodynamic and microscopic reversibility

    SciTech Connect

    Crooks, Gavin E.

    2011-07-12

    The word 'reversible' has two (apparently) distinct applications in statistical thermodynamics. A thermodynamically reversible process indicates an experimental protocol for which the entropy change is zero, whereas the principle of microscopic reversibility asserts that the probability of any trajectory of a system through phase space equals that of the time reversed trajectory. However, these two terms are actually synonymous: a thermodynamically reversible process is microscopically reversible, and vice versa.

  14. Content determination of the flavonoids in the different parts and different species of Abelmoschus esculentus L. by reversed phase-high performance liquid chromatograph and colorimetric method

    PubMed Central

    Lin, Yin; Lu, Min-feng; Liao, Hai-bing; Li, Yu-xian; Han, Wei; Yuan, Ke

    2014-01-01

    Background: This research will establish the ultraviolet colorimetric method to determine the total flavonoid content in different species and different parts of Abelmoschus esculentus L. Materials and Methods: We establish the reversed-phase high-performance liquid chromatograph (RP-HPLC) method to determine the content of the three flavonoid glycosides in different species and different parts of the A. esculentus. Adopt the NaNO2-Al (NO3)3-NaOH colorimetric method to determine the total flavonoid content; at the same time, adopt the RP-HPLC method to determine the contents of the three flavonoid glycosides. Using the methods of ultraviolet colorimetry and RP-HPLC, we determined and analyzed the total flavonoid content and the content of the three flavonoid glycosides in different species and different parts of A. esculentus. Results: There are great distribution differences of the total flavonoids and the three flavonoid glycosides in different species and parts of A. esculentus. Among them, the content of the effective constituents in the flower is relatively high, next is in the fruit. In the different species of A. esculentus, the content of the flavonoids of finger relatively high. The HPLC method established in this research is simple and convenient and its results are accurate and reliable. In addition, it has a very good repeatability. Conclusion: The results provided the reference data for the medicinal use of A. esculentus and it can be used in quality analyzing of its effective constituents. PMID:25210315

  15. Reversible collisionless magnetic reconnection

    SciTech Connect

    Ishizawa, A.; Watanabe, T.-H.

    2013-10-15

    Reversible magnetic reconnection is demonstrated for the first time by means of gyrokinetic numerical simulations of a collisionless magnetized plasma. Growth of a current-driven instability in a sheared magnetic field is accompanied by magnetic reconnection due to electron inertia effects. Following the instability growth, the collisionless reconnection is accelerated with development of a cross-shaped structure of current density, and then all field lines are reconnected. The fully reconnected state is followed by the secondary reconnection resulting in a weakly turbulent state. A time-reversed simulation starting from the turbulent state manifests that the collisionless reconnection process proceeds inversely leading to the initial state. During the reversed reconnection, the kinetic energy is reconverted into the original magnetic field energy. In order to understand the stability of reversed process, an external perturbation is added to the fully reconnected state, and it is found that the accelerated reconnection is reversible when the deviation of the E B streamlines due to the perturbation is comparable with or smaller than a current layer width.

  16. Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation-oxa-Michael reactions with unactivated ketones.

    PubMed

    Johnson, Sherida; Tanaka, Fujie

    2016-01-01

    C-glycosides are important compounds as they are used as bioactive molecules and building blocks. We have developed methods to concisely synthesize C-glycosides from unprotected 2-N-acyl-aldohexoses and unactivated ketones; we designed aldol-condensation-oxa-Michael addition reactions catalyzed by amine-based catalysts using additives. Depending on the conditions used, C-glycosides were stereoselectively obtained. Our methods allowed the C-C bond formations at the anomeric centers of unprotected carbohydrates under mild conditions to lead the C-glycosides in atom- and step-economical ways. PMID:26565955

  17. Structural Analysis of a Family 101 Glycoside Hydrolase in Complex with Carbohydrates Reveals Insights into Its Mechanism.

    PubMed

    Gregg, Katie J; Suits, Michael D L; Deng, Lehua; Vocadlo, David J; Boraston, Alisdair B

    2015-10-16

    O-Linked glycosylation is one of the most abundant post-translational modifications of proteins. Within the secretory pathway of higher eukaryotes, the core of these glycans is frequently an N-acetylgalactosamine residue that is ?-linked to serine or threonine residues. Glycoside hydrolases in family 101 are presently the only known enzymes to be able to hydrolyze this glycosidic linkage. Here we determine the high-resolution structures of the catalytic domain comprising a fragment of GH101 from Streptococcus pneumoniae TIGR4, SpGH101, in the absence of carbohydrate, and in complex with reaction products, inhibitor, and substrate analogues. Upon substrate binding, a tryptophan lid (residues 724-WNW-726) closes on the substrate. The closing of this lid fully engages the substrate in the active site with Asp-764 positioned directly beneath C1 of the sugar residue bound within the -1 subsite, consistent with its proposed role as the catalytic nucleophile. In all of the bound forms of the enzyme, however, the proposed catalytic acid/base residue was found to be too distant from the glycosidic oxygen (>4.3 ) to serve directly as a general catalytic acid/base residue and thereby facilitate cleavage of the glycosidic bond. These same complexes, however, revealed a structurally conserved water molecule positioned between the catalytic acid/base and the glycosidic oxygen. On the basis of these structural observations we propose a new variation of the retaining glycoside hydrolase mechanism wherein the intervening water molecule enables a Grotthuss proton shuttle between Glu-796 and the glycosidic oxygen, permitting this residue to serve as the general acid/base catalytic residue. PMID:26304114

  18. Cardiac Glycoside Activities Link Na+/K+ ATPase Ion-Transport to Breast Cancer Cell Migration via Correlative SAR

    PubMed Central

    2015-01-01

    The cardiac glycosides ouabain and digitoxin, established Na+/K+ ATPase inhibitors, were found to inhibit MDA-MB-231 breast cancer cell migration through an unbiased chemical genetics screen for cell motility. The Na+/K+ ATPase acts both as an ion-transporter and as a receptor for cardiac glycosides. To delineate which function is related to breast cancer cell migration, structure–activity relationship (SAR) profiles of cardiac glycosides were established at the cellular (cell migration inhibition), molecular (Na+/K+ ATPase inhibition), and atomic (computational docking) levels. The SAR of cardiac glycosides and their analogs revealed a similar profile, a decrease in potency when the parent cardiac glycoside structure was modified, for each activity investigated. Since assays were done at the cellular, molecular, and atomic levels, correlation of SAR profiles across these multiple assays established links between cellular activity and specific protein–small molecule interactions. The observed antimigratory effects in breast cancer cells are directly related to the inhibition of Na+/K+ transport. Specifically, the orientation of cardiac glycosides at the putative cation permeation path formed by transmembrane helices αM1–M6 correlates with the Na+ pump activity and cell migration. Other Na+/K+ ATPase inhibitors that are structurally distinct from cardiac glycosides also exhibit antimigratory activity, corroborating the conclusion that the antiport function of Na+/K+ ATPase and not the receptor function is important for supporting the motility of MDA-MB-231 breast cancer cells. Correlative SAR can establish new relationships between specific biochemical functions and higher-level cellular processes, particularly for proteins with multiple functions and small molecules with unknown or various modes of action. PMID:25334087

  19. Thermosensory reversal effect quantified.

    PubMed

    Bergmann Tiest, Wouter M; Kappers, Astrid M L

    2008-01-01

    At room temperature, some materials feel colder than others due to differences in thermal conductivity, heat capacity and geometry. When the ambient temperature is well above skin temperature, the roles of 'cold' and 'warm' materials are reversed. In this paper, this effect is quantified by measuring discrimination thresholds for subjective coldness at different ambient temperatures using stimuli of different thicknesses. The reversal point was found to be at 34 degrees C, somewhat above skin temperature. At this reversal point, discrimination is quite impossible. At room temperature, subjects were able to discriminate between stimuli of different thickness based on subjective coldness, showing that the sense of touch, unlike vision, can penetrate solid objects. Furthermore, somewhat surprisingly, at ambient temperatures well below normal room temperature, discrimination is worse than at room temperature. PMID:17306203

  20. Quantitative determination of flavonoids and cycloartanol glycosides from aerial parts of Sutherlandia frutescens (L.) R. BR. by using LC-UV/ELSD methods and confirmation by using LC–MS method

    PubMed Central

    Avula, Bharathi; Wang, Yan-Hong; Smillie, Troy J.; Fu, Xiang; Li, Xing Cong; Mabusela, Wilfred; Syce, James; Johnson, Quinton; Folk, William; Khan, Ikhlas A.

    2012-01-01

    This paper describes the first analytical method for the determination of four flavonoids (sutherlandins A–D) and four cycloartanol glycosides (sutherlandiosides A–D) from the aerial parts of Sutherlandia frutescens (L.) R. Br. A separation by HPLC was achieved by using a reversed phase (RP-18) column, PDA with ELS detection, and a water/acetonitrile gradient as the mobile phase. The wavelength used for quantification of four flavonoids with the diode array detector was 260 nm. Owing to their low UV absorption, the cycloartanol glycosides were detected by evaporative light scattering. The method was validated for linearity, repeatability, limits of detection (LOD) and limits of quantification (LOQ). The limits of detection and limits of quantification of eight compounds were found to be in the range from 0.1 to 7.5 µg/mL and 0.5 to 25 µg/mL, respectively. The analysis of products showed considerable variation of 1.099–5.224 mg/average weight for the major compound, sutherlandioside B. The eight compounds in plant sample and products of S. frutescens were further confirmed by LC–ESI-TOF. This method involved the use of the [M+H]+ and [M+Na]+ ions in the positive ion mode with extractive ion monitoring (EIM). PMID:20122811

  1. Sequential Polarity-Reversing Circuit

    NASA Technical Reports Server (NTRS)

    Labaw, Clayton C.

    1994-01-01

    Proposed circuit reverses polarity of electric power supplied to bidirectional dc motor, reversible electro-mechanical actuator, or other device operating in direction depending on polarity. Circuit reverses polarity each time power turned on, without need for additional polarity-reversing or direction signals and circuitry to process them.

  2. Effects of pregnane glycosides on food intake depend on stimulation of the melanocortin pathway and BDNF in an animal model.

    PubMed

    Komarnytsky, Slavko; Esposito, Debora; Rathinasabapathy, Thirumurugan; Poulev, Alexander; Raskin, Ilya

    2013-02-27

    Pregnane glycosides appear to modulate food intake by possibly affecting the hypothalamic feeding circuits; however, the mechanisms of the appetite-regulating effect of pregnane glycosides remain obscure. Here, we show that pregnane glycoside-enriched extracts from swamp milkweed Asclepias incarnata at 25-100 mg/kg daily attenuated food intake (up to 47.1 8.5% less than controls) and body weight gain in rats (10% for males and 9% for females, respectively) by activating melanocortin signaling and inhibiting gastric emptying. The major milkweed pregnane glycoside, ikemagenin, exerted its appetite-regulating effect by decreasing levels of agouti-related protein (0.6-fold) but not NPY satiety peptides. Ikemagenin treatment also increased secretion of brain-derived neurotropic factor (BDNF) downstream of melanocortin receptors in the hypothalamus (1.4-fold) and in the C6 rat glioma cell culture in vitro (up to 6-fold). These results support the multimodal effects of pregnane glycosides on feeding regulation, which depends on the activity of the melanocortin signaling pathway and BDNF. PMID:23308358

  3. Molluscicidal activity of cardiac glycosides from Nerium indicum against Pomacea canaliculata and its implications for the mechanisms of toxicity.

    PubMed

    Dai, Lingpeng; Wang, Wanxian; Dong, Xinjiao; Hu, Renyong; Nan, Xuyang

    2011-09-01

    Cardiac glycosides from fresh leaves of Nerium indicum were evaluated for its molluscicidal activity against Pomacea canaliculata (golden apple snail: GAS) under laboratory conditions. The results showed that LC(50) value of cardiac glycosides against GAS was time dependent and the LC(50) value at 96 h was as low as 3.71 mg/L, which was comparable with that of metaldehyde at 72 h (3.88 mg/L). These results indicate that cardiac glycosides could be an effective molluscicide against GAS. The toxicological mechanism of cardiac glucosides on GAS was also evaluated through changes of selected biochemical parameters, including cholinesterase (ChE) and esterase (EST) activities, glycogen and protein contents in hepatopancreas tissues of GAS. Exposure to sublethal concentrations of cardiac glycosides, GAS showed lower activities of EST isozyme in the later stages of the exposure period as well as drastically decreased glycogen content, although total protein content was not affected at the end of 24 and 48 h followed by a significant depletion at the end of 72 and 96 h. The initial increase followed by a decline of ChE activity was also observed during the experiment. These results suggest that cardiac glycosides seriously impair normal physiological metabolism, resulting in fatal alterations in major biochemical constituents of hepatopancreas tissues of P. canaliculata. PMID:21843803

  4. Reversing Flow Test Facility

    NASA Astrophysics Data System (ADS)

    Roach, P. D.

    1986-04-01

    The Reversing Flow Test Facility (RFTF) is intended for the study of fluid flow and heat transfer under the reversing-flow conditions that occur in Stirling engines. The facility consists of four major parts: (1) Mechanical Drive - two cylinders with cam-driven pistons which generate the reversing gas flow, (2) Test Section - a U-shaped section containing instrumented test pieces, (3) Instruments -l high-speed transducers for measuring gas pressure and temperature, piston positions, and other system parameters, and (4) Data Acquisition System - a computer-based system able to acquire, store, display and analyze the data from the instruments. The RFTF can operate at pressures up to 8.0 MPa, hot-side temperatures to 800 deg. C, and flow-reversal frequencies to 50 Hz. Operation to data has used helium as the working gas at pressures of 3.0 and 6.0 MPa, at ambient temperature, and at frequencies from 1 to 50 Hz. The results show that both frictional and inertial parts of the pressure drop are significant in the heater, coolers and connecting tubes; the inertial part is negligible in the regenerators. In all cases, the frictional part of the pressure drop is nearly in phase with the mass flow.

  5. Reverse Coherent Information

    NASA Astrophysics Data System (ADS)

    García-Patrón, Raúl; Pirandola, Stefano; Lloyd, Seth; Shapiro, Jeffrey H.

    2009-05-01

    In this Letter we define a family of entanglement distribution protocols assisted by feedback classical communication that gives an operational interpretation to reverse coherent information, i.e., the symmetric counterpart of the well-known coherent information. This leads to the definition of a new entanglement distribution capacity that exceeds the unassisted capacity for some interesting channels.

  6. Reverse Coherent Information

    NASA Astrophysics Data System (ADS)

    García-Patrón, Raúl; Pirandola, Stefano; Lloyd, Seth; Shapiro, Jeffrey H.

    2009-04-01

    We define a family of entanglement distribution protocols assisted by classical feedback communication that gives an operational interpretation to reverse coherent information, i.e., the symmetric counterpart of the well-known coherent information. This protocol family leads to the definition of a new entanglement distribution capacity that exceeds the unassisted entanglement distribution capacity for some interesting channels.

  7. Time reversal communication system

    DOEpatents

    Candy, James V. (Danville, CA); Meyer, Alan W. (Danville, CA)

    2008-12-02

    A system of transmitting a signal through a channel medium comprises digitizing the signal, time-reversing the digitized signal, and transmitting the signal through the channel medium. The channel medium may be air, earth, water, tissue, metal, and/or non-metal.

  8. Induction of cytotoxic and genotoxic responses by natural and novel quercetin glycosides.

    PubMed

    Engen, Anya; Maeda, Junko; Wozniak, David E; Brents, Colleen A; Bell, Justin J; Uesaka, Mitsuru; Aizawa, Yasushi; Kato, Takamitsu A

    2015-06-01

    The flavonoids quercetin, and its natural glycosides isoquercetin and rutin, are phytochemicals commonly consumed in plant-derived foods. Semi-synthetic water-soluble isoquercetin and rutin glycosides, maltooligosyl isoquercetin, monoglucosyl rutin and maltooligosyl rutin were developed by synthetic glycosylation to overcome solubility challenges for improved incorporation in food and medicinal applications. Quercetin and its natural glycosides are known to induce genetic instability and decrease cell proliferation. Using a system of Chinese hamster ovary (CHO) cells, this study examined the differences in cytotoxic and genotoxic responses induced by natural and synthetic flavonoids. Bioactivity evaluations using poly(ADP-ribose) polymerase (PARP) ELISA showed that the synthetic flavonoids were less effective in inhibiting PARP than the natural flavonoids, where PARP inhibitory effects decreased with glycosylation of flavonoids. In the genotoxic studies, treatments with flavonoids at a concentration range of 0.2 ?M-1 mM induced significant frequencies of sister chromatid exchange (SCE) and micronuclei in CHO cells compared to spontaneous occurrences. The synthetic flavonoids monoglucosyl rutin and maltooligosyl rutin induced less genotoxic effects than the natural flavonoids. However, maltooligosyl isoquercetin induced similar responses as isoquercetin and rutin. The growth inhibition studies showed glycosylation dependent cytotoxicity in natural flavonoids. The quercetin aglycone exhibited the highest toxicity out of all the flavonoids studied. Differences in growth inhibition were not observed between the synthetic flavonoids, maltooligosyl isoquercetin and monoglucosyl rutin, and natural isoquercetin and rutin, respectively. Maltooligosyl rutin induced less cytotoxicity than rutin and monoglucosyl rutin. Our in vitro studies demonstrated that the synthetic flavonoids generally induced less genotoxic responses than their natural counterparts. PMID:26046972

  9. Crystal structure of glycoside hydrolase family 127 β-L-arabinofuranosidase from Bifidobacterium longum

    SciTech Connect

    Ito, Tasuku; Saikawa, Kyo; Kim, Seonah; Fujita, Kiyotaka; Ishiwata, Akihiro; Kaeothip, Sophon; Arakawa, Takatoshi; Wakagi, Takayoshi; Beckham, Gregg T.; Ito, Yukishige; Fushinobu, Shinya

    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.

  10. Profiling of the resin glycoside content of Mexican jalap roots with purgative activity.

    PubMed

    Pereda-Miranda, Rogelio; Fragoso-Serrano, Mabel; Escalante-Sanchez, Edgar; Hernandez-Carlos, Beatriz; Linares, Edelmira; Bye, Robert

    2006-10-01

    Mexican Jalap roots, a prehispanic medicinal plant complex still considered to be a useful laxative, can be found as an ingredient in some over-the-counter products sold by herbalists in contemporary Mexico. The drug is prepared from the dried roots of several morning glories, all of which have been identified as members of the genus Ipomoea. Analysis of several commercial samples was assessed by generating HPLC and 13C NMR spectroscopic profiles of the glycosidic acids obtained through saponification of the resin glycoside contents. These profiles distinguish the three Mexican jalaps currently in frequent use and can serve as analytical tools for the authentication and quality control of these purgative herbal drugs. Ipomoea purga, the authentic "jalap root", yielded two new hexasaccharides of convolvulinic and jalapinolic acids, purgic acids A (1) and B (2), respectively. Scammonic acid A (3), a tetrasaccharide, was produced from Ipomoea orizabensis, the Mexican scammony or false jalap. Operculinic acid B (4), a pentasaccharide, was identified in Ipomoea stans. Semipreparative HPLC was performed to obtain pure samples of new compounds 1 and 2 in sufficient quantity to elucidate their structure by high-field NMR spectroscopy. Purgic acid A (1) was identified as (11S)-hydroxytetradecanoic acid 11-O-beta-D-quinovopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->3)-O-[beta-D-fucopyranosyl-(1-->4)]-O-alpha-L-rhamnopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-quinovopyranoside, while purgic acid B (2) was characterized with (11S)-hydroxyhexadecanoic acid as its aglycon but having the same glycosidation sequence in the oligosaccharide core. PMID:17067162

  11. New perspective on glycoside hydrolase binding to lignin from pretreated corn stover

    SciTech Connect

    Yarbrough, John M.; Mittal, Ashutosh; Mansfield, Elisabeth; Taylor, II, Larry E.; Hobdey, Sarah E.; Sammond, Deanne W.; Bomble, Yannick J.; Crowley, Michael F.; Decker, Stephen R.; Himmel, Michael E.; Vinzant, Todd B.

    2015-12-18

    In this study, non-specific binding of cellulases to lignin has been implicated as a major factor in the loss of cellulase activity during biomass conversion to sugars. It is believed that this binding may strongly impact process economics through loss of enzyme activities during hydrolysis and enzyme recycling scenarios. The current model suggests glycoside hydrolase activities are lost though non-specific/non-productive binding of carbohydrate-binding domains to lignin, limiting catalytic site access to the carbohydrate components of the cell wall.

  12. Stability of black cohosh triterpene glycosides and polyphenols: potential clinical relevance.

    PubMed

    Jiang, Bei; Kronenberg, Fredi; Balick, Michael J; Kennelly, Edward J

    2013-04-15

    Concurrent to a clinical trial of black cohosh for menopausal hot flashes, the long-term stability of the black cohosh, over the duration of the clinical trial, was examined. Analytical results showed that the major constituents, both triterpene glycosides and polyphenols, were stable over the 3-year period of testing. These results indicate that a black cohosh product stored for several years in a controlled environment does not undergo significant changes in its major constituents. These results have implications not only for clinical research in natural products, but for basic science, as well as the dietary supplements industry. PMID:23415548

  13. A set of two diastereomers of cyanogenic glycosides from Passiflora quadrangularis.

    PubMed

    Saeki, Daisuke; Yamada, Takeshi; Kajimoto, Tetsuya; Muraoka, Osamu; Tanaka, Reiko

    2011-08-01

    A set of two diastereomers of phenylcyano glycosides, (7S)- and (7R)-phenylcyanomethyl 1'-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (1, 2), were isolated from the methanol extract of dried vines of P. quadrangularis. The absolute configurations of the benzylic methine centers were determined mainly by the comparison of 13C NMR spectra of these compounds, prunasin (3) and sambunigrin (4), of which the last two cyanoglycosides are known to have (R)- and (S)-configurations, respectively. PMID:21922906

  14. Structures of new phenolic glycosides from the seeds of Cucurbita moschata.

    PubMed

    Li, Fa-Sheng; Xu, Jing; Dou, De-Qiang; Chi, Xiao-Feng; Kang, Ting-Guo; Kuang, Hai Xue

    2009-04-01

    A new phenolic glycoside and three known compounds were isolated from the seeds of Cucurbita moschata. The structures of the new compound was elucidated as phenylcarbinyl 5-O-(4-hydroxy)benzoyl-beta-D-apiofuranosyl (1-->2)-beta-D-glucopyranoside on the basis of spectroscopic analysis and chemical evidence. Three known compounds were identified as 1-O-benzyl[5-O-benzoyl-beta-D-apiofuranosyl(1-->2)]-beta-D-glucopyranoside 2, cucurbitosides C 3 and A 4, by comparison of the spectral data with reported data. Compound 2 was isolated from this plant for the first time. PMID:19475995

  15. Flavonoid Glycosides and Other Hydrophilic Compounds from Flowers of Heterotheca inuloides.

    PubMed

    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. PMID:17221440

  16. Steroidal saponins obtained by biotransformation of total furostanol glycosides from Dioscorea zingiberensis with Absidia coerulea.

    PubMed

    Pang, Xu; Wen, Di; Zhao, Yang; Xiong, Cheng-Qi; Wang, Xiao-Qin; Yu, Li-Yan; Ma, Bai-Ping

    2015-01-30

    Five new steroidal saponins (1-5) were isolated from the fermentation broth of total furostanol glycosides from tubers of Dioscorea zingiberensis C.H. Wright incubated with a fungal, Absidia coerulea AS 3.3389, along with known saponins, zingiberensis new saponin (6), deltonin (7), prosapogenin A of dioscin (8), and protobioside (9), and their structures were established by NMR spectroscopy and mass spectrometry as well as by comparison with previously reported spectral data in the literatures. The induced effects in vitro on rat platelet aggregation of all compounds were evaluated. PMID:25498025

  17. Alkyl-imidazolium glycosides: non-ionic-cationic hybrid surfactants from renewable resources.

    PubMed

    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. PMID:26000863

  18. A new flavonol glycoside from the florets of Carthamus tinctorius L.

    PubMed

    Xie, Xue; Zhou, Jianming; Sun, Lin; Zhang, Hongda; Zhao, Yiwu; Song, Yaling; Wang, Xuejing; Ni, Fuyong; Huang, Wenzhe; Wang, Zhenzhong; Xiao, Wei

    2016-01-01

    One new flavonol glycoside, 6-hydroxykaempferol-3-O-?-D-glucoside-7-O-?-D-glucuronide (1), together with eight known flavonoids and three known quinochalcones, was isolated from the florets of Carthamus tinctorius L. Their structures were determined by extensive spectroscopic analyses. Their cardioprotective effects against H2O2-induced apoptosis in H9c2 cells were also evaluated; compounds 1, 2, 4-5, 7-10 and 12 provided significant protective effects on H2O2-induced H9c2 cells at the concentration of 25?g/mL. PMID:26185946

  19. Synthesis of Pro-Xylane: a new biologically active C-glycoside in aqueous media.

    PubMed

    Cavezza, Alexandre; Boulle, Christophe; Guéguiniat, Amélie; Pichaud, Patrick; Trouille, Simon; Ricard, Louis; Dalko-Csiba, Maria

    2009-02-01

    The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane) was identified as the best activator of GAGs biosynthesis. Pro-Xylane was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic. PMID:19135365

  20. Fast repair of thymine-hydroxyl radical adduct by phenylpropanoid glycosides

    NASA Astrophysics Data System (ADS)

    Wenyan, Li; Zhihua, Zou; Rongliang, Zheng; Changzeng, Wang; Zhongjian, Jia; Side, Yao; Nianyun, Lin

    1997-04-01

    The repair effect on thymine-hydroxyl adduct by phenylpropanoid glycosides (PPG): verbascoside, and pedicularioside A, isolated from Pedicularis, were studied using pulse radiolysis technique. From the analysis of transient absorption spectra, the rapid electron transfer from PPG to T-OH - was observed. Phenoxyl radical of PPG were generated via one-electron-transfer reaction. This result showed that two PPG exhibited repair activities on oxidizing T-OH -. The reaction rate constants of electron transfer from PPGs were 1.27 10 9 and 1.29 10 9 dm 3mol -1s -1 respectively.

  1. Two new steroidal glycosides isolated from the aerial part of Solanum torvum Swartz.

    PubMed

    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-?-d-quinovopyranoside and neochlorogenin 6-O-[?-d-xylopyranosyl-(1?3)-?-d-glucopyranoside], respectively. PMID:23815408

  2. Shamiminol: a new aromatic glycoside from the stem bark of Bombax ceiba.

    PubMed

    Faizi, Shaheen; Zikr-Ur-Rehman, Sadia; Versiani, Muhammad Ali

    2011-12-01

    A new aromatic glycoside, shamiminol was isolated from the stem bark of Bombax ceiba along with the known constituents stigmasta-3,5-diene, lupenone, (+/-)-lyoniresinol 2a-O-beta-D-glucopyranoside and opuntiol, obtained for the first time from this plant. The structure of shamiminol was elucidated on the basis of extensive 1D- and 2D-NMR spectroscopic and mass spectrometric studies as 3,4,5-trimethoxyphenol 1-O-beta-D-xylopyranosyl-(1 --> 2)-beta-D-glucopyranoside (1). PMID:22312733

  3. Two new ent-kaurane-type diterpene glycosides from zucchini (Cucurbita pepo L.) seeds.

    PubMed

    Kikuchi, Takashi; Ando, Hiromi; Maekawa, Ken-Ichiro; Arie, Hiroki; Yamada, Takeshi; Tanaka, Reiko

    2015-12-01

    Two new ent-kaurane diterpene glycosides; 12?-(?-d-glucopyranosyloxy)-7?-hydroxykaurenolide (1) and 7?-(?-d-glucopyranosyloxy)-12?-hydroxykaurenolide (2), a new steroid; (24S)-stigmasta-7,22E,25-trien-3-one (12), and known compounds (3-11, 13-14) were isolated from zucchini (Cucurbita pepo L.) seeds. The absolute structures of 1 and 2 were determined by acid hydrolysis and application of a modified Moscher's method. Furthermore, isolated compounds (1-14), and a derivative, 1a, were evaluated for their inhibitory effects on macrophage activation by an inhibitory assay of nitric oxide (NO) production. PMID:26420344

  4. A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.

    PubMed Central

    Kwon, Yun; Kim, Seong-Hwan; Shin, Yoonho; Bae, Munhyung; Kim, Byung-Yong; Lee, Sang Kook; Oh, Ki-Bong; Shin, Jongheon; Oh, Dong-Chan

    2014-01-01

    Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 13 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116. PMID:24759001

  5. A new phenyl glycoside from the aerial parts of Equisetum hyemale.

    PubMed

    Jin, Mei; Zhang, Changhao; Zheng, Tie; Yao, Dalei; Shen, Le; Luo, Jie; Jiang, Zhe; Ma, Juan; Jin, Xue-Jun; Cui, Jiongmo; Lee, Jung Joon; Li, Gao

    2014-01-01

    A new phenyl glycoside, 2-(sophorosyl)-1-(4-hydroxyphenyl)ethanone (9), was isolated from the ethanolic extract of the aerial parts of Equisetum hyemale L., together with eight known compounds (1-8). The structures of these compounds were elucidated using a combination of spectroscopic analyses and chemical method. Of these nine compounds, 4 and 7 showed hepatoprotective effects towards tacrine-induced cytotoxicity in Hep 3B cells with EC50 values of 42.7 ± 1.5 and 132.6 ± 2.8 μM, respectively. PMID:25117054

  6. Octopus glycosides: multivalent molecular platforms for testing carbohydrate recognition and bacterial adhesion.

    PubMed

    Lindhorst, Thisbe K; Dubber, Michael

    2015-02-11

    Multivalency of carbohydrate-protein interactions is critical for cell adhesion, including attachment of bacteria to their host cells. To investigate specific parameters of multivalency effects, a variety of multivalent glycoconjugates has been designed according to different mimetic approaches. Some 15 years ago, carbohydrates were elaborated as multivalent scaffold molecules for the preparation of carbohydrate-centred 'octopus glycosides' as well as of other carbohydrate-centred glycoconjugates. The beginning of this research is reported from a historical perspective and a selection of interesting applications is highlighted. PMID:25104394

  7. Two new flavonoid glycosides from the whole herbs of Hyssopus officinalis.

    PubMed

    Wang, Nan; Yang, Xiu-Wei

    2010-12-01

    Two new flavonoid glycosides, quercetin 7-O-?-D-apiofuranosyl-(1 ? 2)-?-D-xylopyranoside (1) and quercetin 7-O-?-D-apiofuranosyl-(1 ? 2)-?-D-xylopyranoside 3'-O-?-D-glucopyranoside (2), together with nine known flavonoids were isolated from the whole herbs of Hyssopus officinalis L. cultivated in Xinjiang Uygur Autonomous Region of China. All structures were characterized by the spectroscopic methods including UV, IR, ESI-MS, 1D, and 2D NMR. Their potent free radical scavenging activity against the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical was evaluated. PMID:21128145

  8. A new antimicrobial and radical-scavenging glycoside from Paullinia pinnata var. cameroonensis.

    PubMed

    Lunga, Paul-Keilah; Qin, Xu-Jie; Yang, Xing-Wei; Kuiate, Jules-Roger; Du, Zhi-Zhi; Gatsing, Donatien

    2015-01-01

    A new glycoside, pinnatoside A (1), together with two known compounds (2 and 3), were isolated from the stems of Paullinia pinnata. Their structures were elucidated on the basis of extensive spectroscopic analysis and chemical methods. Compound 1 showed significant antibacterial activity with a minimum inhibitory concentration (MIC) value of 1.56 ?g/mL against Escherichia coli, and 2 displayed significant antibacterial activity with a MIC value of 1.56 ?g/mL against Enterobacter aerogenes and E. coli. Equally, compound 1 exhibited the best radical-scavenging activity (RSa50 = 25.07 0.49 ?g/mL). PMID:25563339

  9. A new ent-kaurane diterpenoid glycoside from Isodon japonica var. glaucocalyx.

    PubMed

    Xiang, Zhao-Bao; Wang, Guang-Li; Huang, Lan-Zhi; Heng, Lin-Sen; Li, Xiao-Hui

    2013-01-01

    A new ent-kaurane diterpenoid glycoside (1), named glaucocalyxin G, has been isolated from the n-butanol-soluble fraction of the dried whole plants of Isodon japonica var. glaucocalyx along with two known compounds, namely arjunglucoside (2) and kaempferol-3-O-rutinoside (3). The structures of the isolated compounds were assigned on the basis of their (1)H and (13)C NMR spectra including two-dimensional NMR techniques such as HMQC, HMBC, and NOESY experiments and comparison with the literature data. PMID:23614395

  10. Patagonicosides B and C, two Antifungal Sulfated Triterpene Glycosides from the Sea Cucumber Psolus patagonicus

    PubMed Central

    Careaga, Valeria P.; Muniain, Claudia; Maier, Marta S.

    2013-01-01

    Two new triterpene glycosides, patagonicosides B (2) and C (3), together with the known patagonicoside A (1), have been isolated from the ethanolic extract of the sea cucumber Psolus patagonicus. The structures of the new compounds were established on the basis of extensive NMR spectroscopy (1H and13C NMR,1H–1H COSY, HMBC, HSQC, TOCSY, and NOESY), HRESIMS, and chemical transformations. Compounds 1–3 and their desulfated analogs showed antifungal activity against the phytopathogenic fungus Cladosporium cladosporoides in a dose dependent activity. PMID:21404430

  11. Acylated flavonol glycosides from Epimedium elatum, a plant endemic to the Western Himalayas.

    PubMed

    Tantry, Mudasir A; Dar, Javid A; Idris, Ahmed; Akbar, Seema; Shawl, Abdul S

    2012-06-01

    Herba Epimedii is a well-known Botanical preparation used over long time in traditional Chinese medicine. The extracts and chemical constituents from Epimedium species are aphrodisiac as well as to treat many ailments. Chemical investigation of lonely species growing in Kashmir Himalaya Epimedium elatum was undertaken to evaluate its chemical profile. Two unusual substituted acylated flavonol glycosides named Elatoside A (1) and Elatoside B (2) have been isolated from the ethanolic extract of E. elatum along with 23 previously known ones (3-25). All isolates were evaluated for antimicrobial and PPAR-? ligand binding activity, and some of them appeared to be modestly active. PMID:22366553

  12. Three new glycosides from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO.

    PubMed

    Kikuchi, Masao; Kakuda, Rie; Kikuchi, Masafumi; Yaoita, Yasunori

    2008-04-01

    Three new glycosides, 7-deoxyloganic acid beta-D-glucopyranosyl ester (1), (3R)-hydrangenol 8,4'-di-O-beta-D-glucopyranoside (2), and (6R,7E,9R)-megastigma-4,7-dien-3-one 9,13-di-O-beta-D-glucopyranoside (3), have been isolated from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO (Saxifragaceae). The structures of 1-3 were elucidated on the basis of spectral data and chemical evidence. PMID:18379120

  13. In silico analysis and molecular docking studies of potential angiotensin-converting enzyme inhibitor using quercetin glycosides

    PubMed Central

    Muhammad, Syed Aun; Fatima, Nighat

    2015-01-01

    The purpose of this study was to analyze the inhibitory action of quercetin glycosides by computational docking studies. For this, natural metabolite quercetin glycosides isolated from buckwheat and onions were used as ligand for molecular interaction. The crystallographic structure of molecular target angiotensin-converting enzyme (ACE) (peptidyl-dipeptidase A) was obtained from PDB database (PDB ID: 1O86). Enalapril, a well-known brand of ACE inhibitor was taken as the standard for comparative analysis. Computational docking analysis was performed using PyRx, AutoDock Vina option based on scoring functions. The quercetin showed optimum binding affinity with a molecular target (angiotensin-converting-enzyme) with the binding energy of ?8.5 kcal/mol as compared to the standard (?7.0 kcal/mol). These results indicated that quercetin glycosides could be one of the potential ligands to treat hypertension, myocardial infarction, and congestive heart failure. PMID:26109757

  14. A new group of exo-acting family 28 glycoside hydrolases of Aspergillus niger that are involved in pectin degradation

    PubMed Central

    Martens-Uzunova, ElenaS.; Zandleven, JorisS.; Benen, JaquesA.E.; Awad, Hanem; Kools, HarrieJ.; Beldman, Gerrit; Voragen, AlphonsG.J.; Van Den Berg, JohanA.; Schaap, PeterJ.

    2006-01-01

    The fungus Aspergillus niger is an industrial producer of pectin-degrading enzymes. The recent solving of the genomic sequence of A. niger allowed an inventory of the entire genome of the fungus for potential carbohydrate-degrading enzymes. By applying bioinformatics tools, 12 new genes, putatively encoding family 28 glycoside hydrolases, were identified. Seven of the newly discovered genes form a new gene group, which we show to encode exoacting pectinolytic glycoside hydrolases. This group includes four exo-polygalacturonan hydrolases (PGAX, PGXA, PGXB and PGXC) and three putative exo-rhamnogalacturonan hydrolases (RGXA, RGXB and RGXC). Biochemical identification using polygalacturonic acid and xylogalacturonan as substrates demonstrated that indeed PGXB and PGXC act as exo-polygalacturonases, whereas PGXA acts as an exo-xylogalacturonan hydrolase. The expression levels of all 21 genes were assessed by microarray analysis. The results from the present study demonstrate that exo-acting glycoside hydrolases play a prominent role in pectin degradation. PMID:16822232

  15. A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides

    PubMed Central

    2010-01-01

    Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis. PMID:21103068

  16. Differential effects on the cyanogenic glycoside content of fermenting cassava root pulp by beta-glucosidase and microbial activities.

    PubMed

    Maduagwu, E N

    1983-03-01

    The degradation of cyanogenic glycosides was studied in spontaneously fermenting cassava root pulp and in fresh pulp samples pretreated to prevent either endogenous beta-glycosidase activity, fermentation, or both. The rate of disappearance of the glycosides, as measured by hydrocyanic acid (HCN) production in situ, in membrane-sterilised media or in samples containing 1% sodium iodoacetate, was comparable with the untreated control in which 85% of the substrate was broken down within 72 h. Pretreatment of the fresh pulp with the beta-glucosidase inhibitor 1,5-gluconolactone (1%) markedly reduced the rate of disappearance of the cyanogens while inclusion of glucose in this test medium at the 3% level appeared to induce some hydrolysis. Loss of bound (glycosidic) cyanide in sterilised medium containing the glucosidase inhibitor was negligible. The results suggest that the contribution of the fermentation process in cyanide detoxification of pulped cassava roots is minimal. PMID:6404010

  17. In silico analysis and molecular docking studies of potential angiotensin-converting enzyme inhibitor using quercetin glycosides.

    PubMed

    Muhammad, Syed Aun; Fatima, Nighat

    2015-05-01

    The purpose of this study was to analyze the inhibitory action of quercetin glycosides by computational docking studies. For this, natural metabolite quercetin glycosides isolated from buckwheat and onions were used as ligand for molecular interaction. The crystallographic structure of molecular target angiotensin-converting enzyme (ACE) (peptidyl-dipeptidase A) was obtained from PDB database (PDB ID: 1O86). Enalapril, a well-known brand of ACE inhibitor was taken as the standard for comparative analysis. Computational docking analysis was performed using PyRx, AutoDock Vina option based on scoring functions. The quercetin showed optimum binding affinity with a molecular target (angiotensin-converting-enzyme) with the binding energy of -8.5 kcal/mol as compared to the standard (-7.0 kcal/mol). These results indicated that quercetin glycosides could be one of the potential ligands to treat hypertension, myocardial infarction, and congestive heart failure. PMID:26109757

  18. Identification of Flavonoid Glycosides in Rosa chinensis Flowers by Liquid Chromatography-tandem Mass Spectrometry in Combination with 13C Nuclear Magnetic Resonance

    PubMed Central

    Qing, Lin-Sen; Xue, Ying; Zhang, Jian-Guang; Zhang, Zhi-Feng; Liang, Jian; Jiang, Yan; Liu, Yi-Ming; Liao, Xun

    2012-01-01

    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 13C 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 13C 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. PMID:22749452

  19. Effect of harvest timing on leaf production and yield of diterpene glycosides in Stevia rebaudiana Bert: a specialty perennial crop for Mississippi

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Stevia rebaundiana (Bertoni), a perennial shrub of the Asteraceae, is one of the most important sources of non-caloric natural sweeteners. Stevias plant extracts and glycosides have been used for several years in Paraguay and Brazil. Several studies suggest that Stevia and its glycosides exert ben...

  20. Quantitative analysis of cycloartane glycosides in black cohosh rhizomes and dietary supplements by RRLC-ELSD and RRLC-qTOF-MS.

    PubMed

    Cicek, Serhat S; Aberham, Anita; Ganzera, Markus; Stuppner, Hermann

    2011-06-01

    In this study, a fast and reproducible RRLC-ELSD method for the quantitative analysis of 17 cycloartane glycosides and the aglycone cimigenol in black cohosh rhizomes and dietary supplements has been developed. Separation of the 18 triterpenes was achieved within 16 min using reversed phase material and a gradient elution system consisting of water, acetonitrile and methanol. The method was validated for accuracy (recovery rates from 96.79% to 102.86%), precision (intra-day variation ?5.98%, inter-day variation ?3.74%), repeatability (R.S.D.???6.94%) and sensitivity, with detection limits below 4.0 ?g/mL and quantification limits lower than 13.2 ?g/mL. Calibration curves were established in the range from 5-1,000 ?g/mL, with correlation coefficients higher than 0.998 for all constituents investigated. Peak purity and peak assignment were confirmed by means of RRLC-qTOF-MS and in comparison with reference compounds. Three different MS sources (ESI, APCI and APPI) were compared for their ionisation potential regarding cycloartane derivatives. One of the isolated black cohosh constituents, 24-O-acetylhydroshengmanol-3-O-?-L-arabinopyranoside, could be identified as new natural compound. PMID:20694806

  1. Cardiac glycosides correct aberrant splicing of IKBKAP-encoded mRNA in familial dysautonomia derived cells by suppressing expression of SRSF3.

    PubMed

    Liu, Bo; Anderson, Sylvia L; Qiu, Jinsong; Rubin, Berish Y

    2013-08-01

    The ability to modulate the production of the wild-type transcript in cells bearing the splice-altering familial dysautonomia (FD) causing mutation in the IKBKAP gene prompted a study of the impact of a panel of pharmaceuticals on the splicing of this transcript, which revealed the ability of the cardiac glycoside digoxin to increase the production of the wild-type, exon-20-containing, IKBKAP-encoded transcript and the full-length I?B-kinase-complex-associated protein in FD-derived cells. Characterization of the cis elements and trans factors involved in the digoxin-mediated effect on splicing reveals that this response is dependent on an SRSF3 binding site(s) located in the intron 5' of the alternatively spliced exon and that digoxin mediates its effect by suppressing the level of the SRSF3 protein. Characterization of the digoxin-mediated effect on the RNA splicing process was facilitated by the identification of several RNA splicing events in which digoxin treatment mediates the enhanced inclusion of exonic sequence. Moreover, we demonstrate the ability of digoxin to impact the splicing process in neuronal cells, a cell type profoundly impacted by FD. This study represents the first demonstration that digoxin possesses splice-altering capabilities that are capable of reversing the impact of the FD-causing mutation. These findings support the clinical evaluation of the impact of digoxin on the FD patient population. PMID:23711097

  2. Effects of hesperidin, a flavanone glycoside interaction on the conformation, stability, and aggregation of lysozyme: multispectroscopic and molecular dynamic simulation studies?

    PubMed

    Ratnaparkhi, Aditi; Muthu, Shivani A; Shiriskar, Sonali M; Pissurlenkar, Raghuvir R S; Choudhary, Sinjan; Ahmad, Basir

    2015-09-01

    Hesperidin (HESP), a flavanone glycoside, shows high antioxidant properties and possess ability to go through the blood-brain barrier. Therefore, it could be a potential drug molecule against aggregation based diseases such as Alzheimer's, Parkinson's, and systemic amyloidoses. In this work, we investigated the potential of HESP to interact with hen egg-white lysozyme (HEWL) monomer and prevent its aggregation. The HESP-HEWL binding studies were performed using a fluorescence quenching technique, molecular docking and molecular dynamics simulations. We found a strong interaction of HESP with the lysozyme monomer (Ka, ~ 5 10(4) M(-1)) mainly through hydrogen bonding, water bridges, and hydrophobic interactions. We showed that HESP molecule spanned the highly aggregation prone region (amino acid residues 48-101) of HEWL and prevented its fibrillar aggregation. Further, we found that HESP binding completely inhibited amorphous aggregation of the protein induced by disulfide-reducing agent tries-(2-carboxyethyl) phosphine. Conformational and stability studies as followed by various tertiary and secondary structure probes revealed that HESP binding only marginally affected the lysozyme monomer conformation and increased both stability and reversibility of the protein against thermal denaturation. Future studies should investigate detail effects of HESP on solvent dynamics, structure, and toxicity of various aggregates. The answers to these questions will not only target the basic sciences, but also have application in biomedical and biotechnological sciences. PMID:25301518

  3. Isolation and purification of six iridoid glycosides from gardenia jasminoides fruit by medium-pressure liquid chromatography combined with macroporous resin chromatography.

    PubMed

    Wang, Yun; Liu, Hui; Shen, Lifeng; Yao, Lan; Ma, Yinlian; Yu, Dingrong; Chen, Jianhong; Li, Puling; Chen, Ying; Zhang, Cun

    2015-12-01

    Gardeniae fructus is one of the most frequently used herbs in traditional Chinese medicine. In the present study, a process for the enrichment of six iridoid glycosides from Gardeniae fructus was developed using medium-pressure liquid chromatography combined with macroporous resin and reversed-phase chromatography. The purities of different fractions from Gardeniae fructus were assessed using quantitative high-performance liquid chromatography. After fractionation using HPD-100 column chromatography, a 30% ethanol fraction was selected based on high-performance liquid chromatography and liquid chromatography with mass spectrometry qualitative analysis to separate and purify. Based on the orientation analysis results, six compounds-deacetyl asperulosidic acid methyl ester, gardenoside, ixoroside, scandoside methyl ester, genipin-1-O-?-d-gentiobioside, and geniposide-were successfully isolated and purified in three to four combined steps from Gardeniae fructus. The purities of these compounds were found by high-performance liquid chromatography analysis to be 97.9, 98.1, 95.5, 96.3, 97.1, and 98.7%, respectively. Moreover, their structures were elucidated by NMR spectroscopy and liquid chromatography with tandem mass spectrometry. The separation process was highly efficient, rapid, and accurate, making it a potential approach for the large-scale production of iridoids in the laboratory and providing several marker compounds for quality control. This procedure may be meaningful for the purification of other natural products used in traditional Chinese medicine. PMID:26768549

  4. Gridded electron reversal ionizer

    NASA Technical Reports Server (NTRS)

    Chutjian, Ara (Inventor)

    1993-01-01

    A gridded electron reversal ionizer forms a three dimensional cloud of zero or near-zero energy electrons in a cavity within a filament structure surrounding a central electrode having holes through which the sample gas, at reduced pressure, enters an elongated reversal volume. The resultant negative ion stream is applied to a mass analyzer. The reduced electron and ion space-charge limitations of this configuration enhances detection sensitivity for material to be detected by electron attachment, such as narcotic and explosive vapors. Positive ions may be generated by generating electrons having a higher energy, sufficient to ionize the target gas and pulsing the grid negative to stop the electron flow and pulsing the extraction aperture positive to draw out the positive ions.

  5. Reversing Glass Wettability

    NASA Technical Reports Server (NTRS)

    Frazier, D. O.; Smith, J. E., Jr.; Kaukler, W. F.

    1985-01-01

    Treatment reverses wettability of glassware: Liquids that normally wet glass no longer do, and those that do not wet glass are made to do so. Useful in research on container effects in nucleation and growth of secondary phase from solution. Treatment consists of spreading 3 percent (by weight) solution of silicone oil in hexane isomers over glass, drying in air, and curing at 300 degrees C in vacuum for one hour.

  6. Reversible Dysphasia and Statins

    PubMed Central

    2012-01-01

    This paper presents a case of reversible dysphasia occurring in a patient prescribed atorvastatin in combination with indapamide. A milder dysphasia recurred with the prescription of rosuvastatin and was documented on clinical examination. This resolved following cessation of rosuvastatin. The case highlights both a need for a wider understanding of potential drug interactions through the CYP 450 system and for an increased awareness, questioning and reporting of drug side-effects. PMID:22468114

  7. Tevatron reverse injection

    SciTech Connect

    Saritepe, S.; Annala, G.

    1993-06-25

    In the new injection scenario antiprotons are injected onto a helical orbit in the Tevatron in order to avoid the detrimental effects of the beam-beam interaction at 150 GeV. The new scenario required changes in the tuning procedure. Antiprotons are too precious to be used for tuning, therefore the antiproton injection line has to be tuned with protons by reverse injecting them from the Tevatron into the Main Pang (MR). Previously, the reverse injection was performed in one supercycle. One batch of uncoalesced bunches was injected into the Tevatron and ejected after 40 seconds. Then the orbit closure was performed in the MR. In the new scheme the lambertson magnets have to be moved and separator polarities have to be switched, activities that cannot be completed in one supercycle. Therefore, the reverse injection sequence was changed. This involved the redefinition of TVBS dock event $D8 as MRBS $D8 thus marking it possible to inject 6 proton batches and eject them one at a time on command, performing orbit closure each time in the MR.

  8. Reversible infantile mitochondrial diseases.

    PubMed

    Boczonadi, Veronika; Bansagi, Boglarka; Horvath, Rita

    2015-05-01

    Mitochondrial diseases are usually severe and progressive conditions; however, there are rare forms that show remarkable spontaneous recoveries. Two homoplasmic mitochondrial tRNA mutations (m.14674T>C/G in mt-tRNA(Glu)) have been reported to cause severe infantile mitochondrial myopathy in the first months of life. If these patients survive the first year of life by extensive life-sustaining measures they usually recover and develop normally. Another mitochondrial disease due to deficiency of the 5-methylaminomethyl-2-thiouridylate methyltransferase (TRMU) causes severe liver failure in infancy, but similar to the reversible mitochondrial myopathy, within the first year of life these infants may also recover completely. Partial recovery has been noted in some other rare forms of mitochondrial disease due to deficiency of mitochondrial tRNA synthetases and mitochondrial tRNA modifying enzymes. Here we summarize the clinical presentation of these unique reversible mitochondrial diseases and discuss potential molecular mechanisms behind the reversibility. Understanding these mechanisms may provide the key to treatments of potential broader relevance in mitochondrial disease, where for the majority of the patients no effective treatment is currently available. PMID:25407320

  9. Reversible DNA compaction.

    PubMed

    Gonzlez-Prez, Alfredo

    2014-01-01

    In this review we summarize and discuss the different methods we can use to achieve reversible DNA compaction in vitro. Reversible DNA compaction is a natural process that occurs in living cells and viruses. As a result these process long sequences of DNA can be concentrated in a small volume (compacted) to be decompacted only when the information carried by the DNA is needed. In the current work we review the main artificial compacting agents looking at their suitability for decompaction. The different approaches used for decompaction are strongly influenced by the nature of the compacting agent that determines the mechanism of compaction. We focus our discussion on two main artificial compacting agents: multivalent cations and cationic surfactants that are the best known compacting agents. The reversibility of the process can be achieved by adding chemicals like divalent cations, alcohols, anionic surfactants, cyclodextrins or by changing the chemical nature of the compacting agents via pH modifications, light induced conformation changes or by redox-reactions. We stress the relevance of electrostatic interactions and self-assembly as a main approach in order to tune up the DNA conformation in order to create an on-off switch allowing a transition between coil and compact states. The recent advances to control DNA conformation in vitro, by means of molecular self-assembly, result in a better understanding of the fundamental aspects involved in the DNA behavior in vivo and serve of invaluable inspiration for the development of potential biomedical applications. PMID:24444152

  10. Studies on the constituents of Syringa species. X. Five new iridoid glycosides from the leaves of Syringa reticulata (Blume) Hara.

    PubMed

    Machida, Koichi; Kaneko, Atsuko; Hosogai, Tomokazu; Kakuda, Rie; Yaoita, Yasunori; Kikuchi, Masao

    2002-04-01

    Five new iridoid glycosides, (8Z)-ligstroside (1), (8Z)-nzhenide (3), 6'-O-alpha-D-glucopyranosylsyringopicroside (4), 3'-O-beta-D-glucopyranosylsyringopicroside (5) and 4'-O-beta-D-glucopyranosylsyringopicroside (6) were isolated, together with a known one, (8E)-nzhenide (2), from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compounds 1 and 3 are the first findings of a (8Z)-oleoside-type secoiridoid. Compound 4 is the first naturally occurring iridoid di-glycoside having an isomaltose. PMID:11963996

  11. Studies on the constituents of Syringa species. XII. New glycosides from the leaves of Syringa reticulata (BLUME) HARA.

    PubMed

    Machida, Koichi; Unagami, Eriko; Ojima, Hiromi; Kikuchi, Masao

    2003-07-01

    Three new glycosides, 6'-O-alpha-D-galactopyranosylsyringopicroside (1), secologanoside 7-methyl ester (2) and (+)-lariciresinol 4'-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside (3), were isolated from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compound 1 is the first naturally occurring iridoid di-glycoside having melibiose. Comparison of the spectral data of 2 and that previously recognized as secologanoside 7-methyl ester led to the conclusion that the recognized structure should be revised to the sodium salt of secoxyloganin (2'). PMID:12843604

  12. [Effect of triterpene glycosides on the plasma membrane permeability for amino acids in Saccharomyces carlsbergensis yeast cells].

    PubMed

    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. PMID:623450

  13. Biosynthesis of malonylated flavonoid glycosides on the basis of malonyltransferase activity in the petals of Clitoria ternatea.

    PubMed

    Kogawa, Koichiro; Kazuma, Kohei; Kato, Naoki; Noda, Naonobu; Suzuki, Masahiko

    2007-07-01

    The crude malonyltransferase from the petals of Clitoria ternatea was characterized enzymatically to investigate its role on the biosynthetic pathways of anthocyanins and flavonol glycosides. In C. ternatea, a blue flower cultivars (DB) and mauve flower variety (WM) accumulate polyacylated anthocyanins (ternatins) and delphinidin 3-O-(6''-O-malonyl)-beta-glucoside which is one of the precursors of ternatins, respectively. Moreover, WM accumulates minor delphinidin glycosides - 3-O-beta-glucoside, 3-O-(2''-O-alpha-rhamnosyl)-beta-glucoside, 3-O-(2''-O-alpha-rhamnosyl-6''-O-malonyl)-beta-glucoside of delphinidin. These glycosidic patterns for minor anthocyanins in WM are also found among the minor flavonol glycosides in all the varieties including a white flower variety (WW) although the major flavonol glycosides are 3-O-(2''-O-alpha-rhamnosyl)-beta-glucoside, 3-O-(6''-O-alpha-rhamnosyl)-beta-glucoside, 3-O-(2'',6''-di-O-alpha-rhamnosyl)-beta-glucoside of kaempferol, quercetin, and myricetin. How do the enzymatic characteristics affect the variety of glycosidic patterns in the flavonoid glycoside biosynthesis among these varieties? While the enzyme from DB highly preferred delphinidin 3-O-beta-glucoside in the presence of malonyl-CoA, it also has a preference for other anthocyanidin 3-O-beta-glucosides. It could use flavonol 3-O-beta-glucosides in much lower specific activities than anthocyanins; however, it could not utilize 3-O-(2''-O-alpha-rhamnosyl)-beta-glucosides of anthocyanins and flavonols, and 3,3'-di- and 3,3',5'-tri-O-beta-glucoside of delphinidin - other possible precursors in ternatins biosynthesis. It highly preferred malonyl-CoA as an acyl donor in the presence of delphinidin 3-O-beta-glucoside. The crude enzymes prepared from WM and WW had the same enzymatic characteristics. These results suggested that 3-O-(2''-O-alpha-rhamnosyl-6''-O-malonyl)-beta-glucosides of flavonoids were synthesized via 3-O-(6''-O-malonyl)-beta-glucosides rather than via 3-O-(2''-O-alpha-rhamnosyl)-beta-glucosides, and that malonylation proceeded prior to glucosylation at the B-ring of delphinidin in the early biosynthetic steps towards ternatins. It seemed that the substrate specificities largely affected the difference in the accumulated amount of malonylated glycosides between anthocyanins and flavonols although they are not simply proportional to the accumulation ratio. This enzyme might join in the production of both malonylanthocyanins and flavonol malonylglycosides as a result of broad substrate specificities towards flavonoid 3-O-beta-glucosides. PMID:16887235

  14. Species restriction of the mitogenicity induced by lanatoside C. Lymphocyte activation by digitalis glycosides is confined to cells from digitalis resistant species.

    PubMed Central

    Hammarstrm, L; Smith, C I

    1979-01-01

    Activation of Na+, K+-ATPase has previously been suggested to be the triggering signal in mitogen-induced cell activation. Using a digitalis glycoside known to be a potent polyclonal B-cell activator, this hypothesis could be tested since digitalis activates ATPase at different concentrations in various species, depending on the degree of sensitivity to the toxic effects of glycosides. Lanatoside C was found to stimulate lymphocytes from glycoside resistant species such as rat, mouse and hamster. The possible involvement of Na+, K+-ATPase was made less likely by the similarity in dose--response profile in these cells although they have been reported to display varying degrees of glycoside resistance. Furthermore, using lymphocytes from digitalis-sensitive species such as man, guinea-pig or rabbit, no mitogenicity could be recorded, strongly suggesting a lack of correlation between glycoside-induced effects on Na+, K+-ATPase and cell activation. PMID:157324

  15. Salicylic Acid Treatment Increases the Levels of Triterpene Glycosides in Black Cohosh (Actaea Racemosa) Rhizomes.

    PubMed

    De Capite, Annette; Lancaster, Tyler; Puthoff, David

    2016-01-01

    Black cohosh (Actaea racemosa) serves as the host plant for the Appalachian azure butterfly, Celastrina neglectamajor. Overharvesting of Black cohosh for the dietary supplement industry may result in its extirpation, and may also cause the elimination of the dependent butterfly. One way to increase or maintain the number of host plants in forested environments would be to reduce the number harvested, for example by increasing the levels of the desired metabolites in Black cohosh rhizomes. The secondary metabolites actein and deoxyactein are triterpene glycosides and are among the compounds associated with the putative activity of Black cohosh extracts. Acetein and deoxyacetein are used to standardize Black cohosh supplements. To gain an understanding of mechanisms that may control actein and deoxyactein accumulation, Black cohosh rhizomes were treated with exogenous salicylic acid, jasmonic acid, or ethylene, or were mechanically wounded. Salicylic acid treatment significantly increased the levels of actein and deoxyactein in the rhizome of Black cohosh, suggesting that the synthesis of triterpene glycosides is controlled in part by salicylic acid. Using salicylic acid or related chemicals to increase the levels of actein and deoxyactein in rhizomes may help supply the supplement industry and, simultaneously, help conserve Black cohosh and species dependent upon it. PMID:26634573

  16. Comparative analysis of glycoside hydrolases activities from phylogenetically diverse marine bacteria of the genus Arenibacter.

    PubMed

    Bakunina, Irina; Nedashkovskaya, Olga; Balabanova, Larissa; Zvyagintseva, Tatyana; Rasskasov, Valery; Mikhailov, Valery

    2013-06-01

    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 ?-N-acetylglucosaminidases and ?-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

  17. Ability of human oral microbiota to produce wine odorant aglycones from odourless grape glycosidic aroma precursors.

    PubMed

    Muoz-Gonzlez, Carolina; Cueva, Carolina; ngeles Pozo-Bayn, 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. PMID:25977005

  18. Comparison of the inhibitory effects of delphinidin and its glycosides on cell transformation.

    PubMed

    Sogo, Takayuki; Kumamoto, Takuma; Ishida, Hisako; Hisanaga, Ayami; Sakao, Kozue; Terahara, Norihiko; Wada, Koji; Hou, De-Xing

    2015-01-01

    Although anthocyanins are major forms distributed in many plant foods and promising as chemopreventive source, many molecular data are obtained from anthocyanidins, showing their low bioavailability. This study aims to clarify the inhibitory effects of delphinidin glycosides on cell transformation comparing them to those of delphinidin. Screening data revealed that delphinidin 3-sambubioside could directly bind to MAPK/ERK kinase 1. Affinity assay data confirmed that delphinidin 3-sambubioside had higher binding affinity to MAPK/ERK kinase 1 than ERK1/2 and B-Raf. Colony assay data further demonstrated that delphinidin 3-sambubioside inhibited 12-O- tetradecanoylphorbol-13-acetate-induced phosphorylation of MAPK/ERK kinase 1 and sequentially suppressed cell transformation. All of these effects caused by delphinidin 3-sambubioside were weaker than those by its aglycon, delphinidin. Our data suggested that the weaker anti- transformation activity of delphinidin glycosides compared to that of their aglycon is due to lower binding affinity to the target molecule MAPK/ERK kinase 1. PMID:25469858

  19. Discovery of Selective Small-Molecule Activators of a Bacterial Glycoside Hydrolase**

    PubMed Central

    Darby, John F; Landstrm, Jens; Roth, Christian; He, Yuan; Davies, Gideon J; Hubbard, Roderick E

    2014-01-01

    Fragment-based approaches are used routinely to discover enzyme inhibitors as cellular tools and potential therapeutic agents. There have been few reports, however, of the discovery of small-molecule enzyme activators. Herein, we describe the discovery and characterization of small-molecule activators of a glycoside hydrolase (a bacterial O-GlcNAc hydrolase). A ligand-observed NMR screen of a library of commercially available fragments identified an enzyme activator which yielded an approximate 90?% increase in kcat/KM?values (kcat=catalytic rate constant; KM=Michaelis constant). This compound binds to the enzyme in close proximity to the catalytic center. Evolution of the initial hits led to improved compounds that behave as nonessential activators effecting both KM?and Vmax?values (Vmax=maximum rate of reaction). The compounds appear to stabilize an active closed form of the enzyme. Such activators could offer an orthogonal alternative to enzyme inhibitors for perturbation of enzyme activity in?vivo, and could also be used for glycoside hydrolase activation in many industrial processes. PMID:25291993

  20. HPLC-MSn identification and quantification of flavonol glycosides in 28 wild and cultivated berry species.

    PubMed

    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. PMID:22980782

  1. Structural studies on O- and N-glycosidically linked carbohydrate chains on Collocalia mucin.

    PubMed

    Hanisch, F G; Uhlenbruck, G

    1984-02-01

    Oligosaccharides, which are O- and N-glycosidically linked on salivary glycoproteins from the edible bird's nest of chinese swallows, were released by alkaline borohydride treatment of the asialoglycoproteins and fractionated by gel chromatography. Fract. VN1 (oligosaccharides greater than 2 000 dalton) apparently represented a mixture of saccharides derived from complex, N-glycosidically linked glycans (molar ratio Man/GlcNAc/Gal 3:4:8), while fractions VN2 (tetra- to hexasaccharides), VN3 (trisaccharide) and VN4 (disaccharide) were free of mannose, but did contain all the N-acetylgalactosamine released from the protein as its alditol. Oligosaccharides in Fract. VN2 and VN4 were purified by high-performance liquid chromatography, paper chromatography and thin-layer chromatography, methylated and analysed after total or partial acid hydrolysis by gas-liquid chromatography-mass spectrometry. The structures of a hexasaccharide in Fract. VN2/6 and of a tetrasaccharide in fraction VN2/4 were finally established after methylation through direct-probe mass spectrometry: Gal(1----4)GlcNAc(1----3)Gal(1----4)GlcNAc(1----3)Gal(1----3)GalNAc- ol and Gal(1----4)GlcNAc(1----6)[Gal(1----3)]GalNAc-ol. Mass spectrometrical and gas-chromatographical data obtained for a disaccharide in Fract. VN4 were identical with those for Gal(beta 1----3)GalNAc-ol. PMID:6714940

  2. Differential Recognition and Hydrolysis of Host Carbohydrate Antigens by Streptococcus pneumoniae Family 98 Glycoside Hydrolases

    SciTech Connect

    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.

  3. Response surface methodology to optimise Accelerated Solvent Extraction of steviol glycosides from Stevia rebaudiana Bertoni leaves.

    PubMed

    Jentzer, Jean-Baptiste; Alignan, Marion; Vaca-Garcia, Carlos; Rigal, Luc; Vilarem, Grard

    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%. PMID:25053094

  4. Influence of drying method on steviol glycosides and antioxidants in Stevia rebaudiana leaves.

    PubMed

    Periche, Angela; Castell, Mara 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. PMID:25442516

  5. Fast methodology of analysing major steviol glycosides from Stevia rebaudiana leaves.

    PubMed

    Lorenzo, Cndida; Serrano-Daz, Jssica; Plaza, Miguel; Quintanilla, Carmen; Alonso, Gonzalo L

    2014-08-15

    The aim of this work is to propose an HPLC method for analysing major steviol glycosides as well as to optimise the extraction and clarification conditions for obtaining these compounds. Toward this aim, standards of stevioside and rebaudioside A with purities ?99.0%, commercial samples from different companies and Stevia rebaudiana Bertoni leaves from Paraguay supplied by Insobol, S.L., were used. The analytical method proposed is adequate in terms of selectivity, sensitivity and accuracy. Optimum extraction conditions and adequate clarification conditions have been set. Moreover, this methodology is safe and eco-friendly, as we use only water for extraction and do not use solid-phase extraction, which requires solvents that are banned in the food industry to condition the cartridge and elute the steviol glycosides. In addition, this methodology consumes little time as leaves are not ground and the filtration is faster, and the peak resolution is better as we used an HPLC method with gradient elution. PMID:24679813

  6. Identification, quantification, and sensory characterization of steviol glycosides from differently processed Stevia rebaudiana commercial extracts.

    PubMed

    Espinoza, Mara Ins; 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. PMID:25393842

  7. Expression and crystallization of a bacterial glycoside hydrolase family 116 β-glucosidase from Thermoanaerobacterium xylanolyticum.

    PubMed

    Sansenya, Sompong; Mutoh, Risa; Charoenwattanasatien, Ratana; Kurisu, Genji; Ketudat Cairns, James R

    2015-01-01

    The Thermoanaerobacterium xylanolyticum gene product TxGH116, a glycoside hydrolase family 116 protein of 806 amino-acid residues sharing 37% amino-acid sequence identity over 783 residues with human glucosylceramidase 2 (GBA2), was expressed in Escherichia coli. Purification by heating, immobilized metal-affinity and size-exclusion chromatography produced >90% pure TxGH116 protein with an apparent molecular mass of 90 kDa on SDS-PAGE. The purified TxGH116 enzyme hydrolyzed the p-nitrophenyl (pNP) glycosides pNP-β-D-glucoside, pNP-β-D-galactoside and pNP-N-acetyl-β-D-glucopyranoside, as well as cellobiose and cellotriose. The TxGH116 protein was crystallized using a precipitant consisting of 0.6 M sodium citrate tribasic, 0.1 M Tris-HCl pH 7.0 by vapour diffusion with micro-seeding to form crystals with maximum dimensions of 120×25×5 µm. The TxGH116 crystals diffracted X-rays to 3.15 Å resolution and belonged to the monoclinic space group P2(1). Structure solution will allow a structural explanation of the effects of human GBA2 mutations. PMID:25615966

  8. Topical Anti-Inflammatory Effects of Isorhamnetin Glycosides Isolated from Opuntia ficus-indica

    PubMed Central

    Antunes-Ricardo, Marilena; Gutirrez-Uribe, Janet A.; Martnez-Vitela, Carlos; Serna-Saldvar, 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-) ?, 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-?, and IL-6 production. IGR seems to be a suitable natural compound for development of new anti-inflammatory ingredient. PMID:25821823

  9. Targeted Discovery of Glycoside Hydrolases from a Switchgrass-Adapted Compost Community

    PubMed Central

    Allgaier, Martin; Reddy, Amitha; Park, Joshua I.; Ivanova, Natalia; D'haeseleer, Patrik; Lowry, Steve; Sapra, Rajat; Hazen, Terry C.; Simmons, Blake A.; VanderGheynst, Jean S.; Hugenholtz, Philip

    2010-01-01

    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, ∼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. PMID:20098679

  10. Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition.

    PubMed

    Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicol; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado

    2015-11-25

    A small library of polymethoxystilbene glycosides (20-25) related to the natural polyphenol resveratrol have been synthesized and subjected, together with their aglycones 17-19, to an antiproliferative activity bioassay toward Caco-2 and SH-SY5Y cancer cells. Six of the compounds exhibit antiproliferative activity against at least one cell line. In particular, compounds 17 and 18 proved highly active on at least one of the two cell cultures. Compound 18 showed a GI50 value of 3 ?M against Caco-2 cells, a value comparable to that of the anticancer drug 5-fluorouracil. The closely related compound 19 proved inactive, and its conjugates 22 and 25 showed weak cell growth inhibition. The results indicate that minimal differences in the structure of both polymethoxystilbenes and their glycosides can substantially affect the antiproliferative activity. The possible hydrolytic release of the aglycones 17-19 by ?-glucosidase or ?-galactosidase was also evaluated. Compounds 20-25 were also tested as potential ?-glucosidase, ?-galactosidase, and ?-glucosidase inhibitors. A promising inhibitory activity toward ?-glucosidase was observed for 21 (IC50 = 78 ?M) and 25 (IC50 = 70 ?M), which might be indicative of their potential as lead compounds for development of antidiabetic or antiobesity agents. PMID:26539626

  11. Rapid differentiation of isobaric and positional isomers of structurally related glycosides from Phytolacca bogotensis.

    PubMed

    Montoya, Guillermo; Arango, Gabriel J; Ramrez-Pineda, Jos R

    2009-11-01

    Through the action of glycosyltransferases, a plant can biosynthetically assemble small different aglycons or 'templates' to various polysaccharides to produce numerous glycoconjugates differing in the type of the attached aglycon, the anomeric configuration of C-1 of the glycosylating sugar, the type of sugar and the different position of attachments of the sugar unit present in the polysaccharide chain. The position of attachments and the anomeric configuration of the different sugar present in the polysaccharide create the opportunity to generate molecules with either the same or very close molecular weights, which have relative structural similarity--forming isobaric and positional isomers. Although isomeric differentiation was once considered outside of the domain of mass spectrometry, this task can now be resolved using tandem mass spectrometry. In a standardized purified glycoconjugate fraction (SPT01) from Phytolacca bogotensis, we report conventional electrospray ionization mass spectrometry and collision-induced dissociation (CID) MS/MS parameters which favored the formation of characteristic product ions. This allowed us to suggest the type of sugar linkages present in a specific glycoconjugate. Ten new glycoconjugate are described from this plant and another twelve known saponins were structurally characterized using the automatic MSn acquisition mode. The differentiation of two pairs of positional isomers and four isobaric glycosides and the production of a library of 30 glycosides present in P. bogotensis were accomplished. PMID:19785003

  12. Production of oleanolic acid glycosides by hairy root established cultures of Calendula officinalis L.

    PubMed

    D?ugosz, Marek; Wiktorowska, Ewa; Wi?niewska, Anita; P?czkowski, 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 ?-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. PMID:24040627

  13. Topical anti-inflammatory effects of isorhamnetin glycosides isolated from Opuntia ficus-indica.

    PubMed

    Antunes-Ricardo, Marilena; Gutirrez-Uribe, Janet A; Martnez-Vitela, Carlos; Serna-Saldvar, 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-) ?, 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-?, and IL-6 production. IGR seems to be a suitable natural compound for development of new anti-inflammatory ingredient. PMID:25821823

  14. Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents.

    PubMed

    Gauthier, Charles; Legault, Jean; Lebrun, Maxime; Dufour, Philippe; Pichette, Andr

    2006-10-01

    The weak hydrosolubility of betulinic acid (3) hampers the clinical development of this natural anticancer agent. In order to circumvent this problem and to enhance the pharmacological properties of betulinic acid (3) and the lupane-type triterpenes lupeol (1), betulin (2), and methyl betulinate (7), glycosides (beta-D-glucosides, alpha-L-rhamnosides, and alpha-D-arabinosides) were synthesized and in vitro tested for cytotoxicity against three cancerous (A-549, DLD-1, and B16-F1) and one healthy (WS1) cell lines. The addition of a sugar moiety at the C-3 or C-28 position of betulin (2) resulted in a loss of cytotoxicity. In contrast, the 3-O-beta-D-glucosidation of lupeol (1) improved the activity by 7- to 12-fold (IC50 14-15.0 microM). Moreover, the results showed that cancer cell lines are 8- to 12-fold more sensitive to the 3-O-alpha-L-rhamnopyranoside derivative of betulinic acid (IC50 2.6-3.9 microM, 22) than the healthy cells (IC50 31 microM). Thus, this study indicates that 3-O-glycosides of lupane-type triterpenoids represent an interesting class of potent in vitro cytotoxic agents. PMID:16787747

  15. The first alpha-1,3-glucosidase from bacterial origin belonging to glycoside hydrolase family 31.

    PubMed

    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. PMID:19683032

  16. The cytotoxic activities of cardiac glycosides from Streptocaulon juventas and the structure-activity relationships.

    PubMed

    Xue, Rui; Han, Na; Ye, Chun; Wang, Lihui; Yang, Jingyu; Wang, Yu; Yin, Jun

    2014-10-01

    A series of cardiac glycosides were isolated and identified from the anti-tumor fraction of the root of Streptocaulon juventas in previous studies. In the present research, the cytotoxic activities of the 43 cardiac glycosides on three cell lines, human lung A549 adenocarcinoma cell, large cell lung cancer NCI-H460 cell and normal human fetal lung fibroblast MRC-5 cell, were evaluated in vitro. Most of the tested compounds showed potent inhibitory activities toward the three cell lines. Then, the structure-activity relationships were discussed in detail. It was indicated that hydroxyl and acetyl groups at C-16 increased the activity, whereas hydroxyl group at C-1 and C-5 can both increase and decrease the activity. Two glucosyl groups which were connected by C1'?C6' showed better inhibitory activity against cancer cell lines, while the C1'?C4' connection showed stronger inhibitory activity against the normal cell line. Also, this is the first report that the activities of these compounds exhibited different variation trends between A549 and NCI-H460 cell lines, which indicated that these compounds could selectively inhibit the cell growth. The results would lay a foundation for further research on new anti-tumor drug development. PMID:25128424

  17. Zebrafish bioassay-guided microfractionation identifies anticonvulsant steroid glycosides from the Philippine medicinal plant Solanum torvum.

    PubMed

    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. PMID:25127088

  18. Glycosidic Enzyme Activity in Pea Tissue and Pea-Fusarium solani Interactions 12

    PubMed Central

    Nichols, Everett J.; Beckman, Jean M.; Hadwiger, Lee A.

    1980-01-01

    Membrane barriers which prevent direct contact between Fusarium solani and pea endocarp tissue prevent fungal spores from inducing phytoalexin production. Conversely, preinduced host resistance responses are not readily transported from the plant across the membrane barrier to Fusarium macroconidia. Crude enzyme extracts from pea endocarp tissues partially degrade Fusarium solani f. sp. phaseoli cell walls. Activities of the glycosidic enzymes, chitinase, ?-1,3-glucanase, chitosanase, ?-D-N-acetylglucosaminidase, ?-D-N-acetylgalactosaminidase, ?-D-glucosidase, ?-D-glucosidase, and ?-D-mannosidase, were detected in pea endocarp tissue. If pods are challenged with Fusarium spores or chitosan, the chitinase activity of the infected tissue remains higher than water-treated pods 0.5 to 6 hours after treatment. The ?-1,3-glucanase activity increases within 6 hours in both inoculated and control tissue. Chitosanase activity was lower in tissue treated with Fusarium solani f. sp. pisi, f. sp. phaseoli or chitosan than in water-treated control tissue. Thus, the pea tissue contains glycosidic enzymes with the potential to degrade the major compounds of the Fusarium cell walls. PMID:16661404

  19. Development of a High Throughput Platform for Screening Glycoside Hydrolases Based on Oxime-NIMS.

    PubMed

    Deng, Kai; Guenther, Joel M; Gao, Jian; Bowen, Benjamin P; Tran, Huu; Reyes-Ortiz, Vimalier; Cheng, Xiaoliang; Sathitsuksanoh, Noppadon; Heins, Richard; Takasuka, Taichi E; Bergeman, Lai F; Geertz-Hansen, Henrik; Deutsch, Samuel; Loqu, Dominique; Sale, Kenneth L; Simmons, Blake A; Adams, Paul D; Singh, Anup K; Fox, Brian G; Northen, Trent R

    2015-01-01

    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 on 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 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. PMID:26528471

  20. Cyanogenic glycosides in plant-based foods available in New Zealand.

    PubMed

    Cressey, Peter; Saunders, Darren; Goodman, Janet

    2013-01-01

    Cyanogenic glycosides occur in a wide range of plant species. The potential toxicity of cyanogenic glycosides arises from enzymatic degradation to produce hydrogen cyanide, which may result in acute cyanide poisoning and has also been implicated in the aetiology of several chronic diseases. One hundred retail foods were sampled and analysed for the presence of total hydrocyanic acid using an acid hydrolysis-isonicotinic/barbituric acid colourimetric method. Food samples included cassava, bamboo shoots, almonds and almond products, pome fruit products, flaxseed/linseed, stone fruit products, lima beans, and various seeds and miscellaneous products, including taro leaves, passion fruit, spinach and canned stuffed vine leaves. The concentrations of total hydrocyanic acid (the hydrocyanic acid equivalents of all cyanogenic compounds) found were consistent with or lower than concentrations reported in the scientific literature. Linseed/flaxseed contained the highest concentrations of total hydrocyanic acid of any of the analysed foods (91-178 mg kg(-1)). Linseed-containing breads were found to contain total hydrocyanic acid at concentrations expected from their linseed content, indicating little impact of processing on the total hydrocyanic acid content. Simulation modelling was used to assess the risk due to the total hydrocyanic acid in fruit juice and linseed-containing bread.  PMID:23984870

  1. Pretreatment of baicalin and wogonoside with glycoside hydrolase: A promising approach to enhance anticancer potential

    PubMed Central

    YU, CHUNHAO; ZHANG, ZHIYU; ZHANG, HAIJIANG; ZHEN, ZHONG; CALWAY, TYLER; WANG, YUNWEI; YUAN, CHUN-SU; WANG, CHONG-ZHI

    2013-01-01

    Previous phytochemical studies showed that the major flavonoids in Scutellaria baicalensis are baicalin, baicalein, wogonoside and wogonin. The two glycosides (baicalin and wogonoside) can be transformed into their aglycons (baicalein and wogonin), which possess positive anticancer potential. In this study, we used glycosidase to catalyze flavonoids in S. baicalensis to enhance the herb’s anticancer activities. Our HPLC data showed that, using the optimized conditions obtained in our experiments (20 U/g of cellulase, 50ºC, pH 4.8 and treatment for 8 h), there was a marked transformation from the two glycosides to their aglycons. The anticancer activity was subsequently evaluated using a series of S. baicalensis extracts in which variable lengths of glycosidase treatment time were used. Combining analytical and bioassay results, we observed that the higher the aglycon content, the stronger the antiproliferation effects. Compared to the untransformed control, 8 h of glycosidase catalyzing significantly increased antiproliferative activity on human colorectal and breast cancer cells, and its cancer cell growth inhibition is, in part, mediated by cell cycle arrest at the S-phase and induction of apoptosis. Data from this study suggest that using glycosidase to catalyze S. baicalensis offers a promising approach to increase its anticancer activity. PMID:24026776

  2. Biogenesis of C-glycosyl flavones and profiling of flavonoid glycosides in lotus (Nelumbo nucifera).

    PubMed

    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

  3. Biogenesis of C-Glycosyl Flavones and Profiling of Flavonoid Glycosides in Lotus (Nelumbo nucifera)

    PubMed Central

    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

  4. Development of a High Throughput Platform for Screening Glycoside Hydrolases Based on Oxime-NIMS

    PubMed Central

    Deng, Kai; Guenther, Joel M.; Gao, Jian; Bowen, Benjamin P.; Tran, Huu; Reyes-Ortiz, Vimalier; Cheng, Xiaoliang; Sathitsuksanoh, Noppadon; Heins, Richard; Takasuka, Taichi E.; Bergeman, Lai F.; Geertz-Hansen, Henrik; Deutsch, Samuel; Loqué, Dominique; Sale, Kenneth L.; Simmons, Blake A.; Adams, Paul D.; Singh, Anup K.; Fox, Brian G.; Northen, Trent R.

    2015-01-01

    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 on 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 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. PMID:26528471

  5. Structural Elucidation of Dextran Degradation Mechanism by Streptococcus mutans Dextranase Belonging to Glycoside Hydrolase Family 66*

    PubMed Central

    Suzuki, Nobuhiro; Kim, Young-Min; Fujimoto, Zui; Momma, Mitsuru; Okuyama, Masayuki; Mori, Haruhide; Funane, Kazumi; Kimura, Atsuo

    2012-01-01

    Dextranase is an enzyme that hydrolyzes dextran ?-1,6 linkages. Streptococcus mutans dextranase belongs to glycoside hydrolase family 66, producing isomaltooligosaccharides of various sizes and consisting of at least five amino acid sequence regions. The crystal structure of the conserved fragment from Gln100 to Ile732 of S. mutans dextranase, devoid of its N- and C-terminal variable regions, was determined at 1.6 resolution and found to contain three structural domains. Domain N possessed an immunoglobulin-like ?-sandwich fold; domain A contained the enzyme's catalytic module, comprising a (?/?)8-barrel; and domain C formed a ?-sandwich structure containing two Greek key motifs. Two ligand complex structures were also determined, and, in the enzyme-isomaltotriose complex structure, the bound isomaltooligosaccharide with four glucose moieties was observed in the catalytic glycone cleft and considered to be the transglycosylation product of the enzyme, indicating the presence of four subsites, ?4 to ?1, in the catalytic cleft. The complexed structure with 4?,5?-epoxypentyl-?-d-glucopyranoside, a suicide substrate of the enzyme, revealed that the epoxide ring reacted to form a covalent bond with the Asp385 side chain. These structures collectively indicated that Asp385 was the catalytic nucleophile and that Glu453 was the acid/base of the double displacement mechanism, in which the enzyme showed a retaining catalytic character. This is the first structural report for the enzyme belonging to glycoside hydrolase family 66, elucidating the enzyme's catalytic machinery. PMID:22337884

  6. Targeted discovery of glycoside hydrolases from a switchgrass-adapted compost community

    SciTech Connect

    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. Targeted Discovery of Glycoside Hydrolases from a Switchgrass-Adapted Compost Community

    SciTech Connect

    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.

  8. Reversible brazing process

    DOEpatents

    Pierce, Jim D. (Albuquerque, NM); Stephens, John J. (Albuquerque, NM); Walker, Charles A. (Albuquerque, NM)

    1999-01-01

    A method of reversibly brazing surfaces together. An interface is affixed to each surface. The interfaces can be affixed by processes such as mechanical joining, welding, or brazing. The two interfaces are then brazed together using a brazing process that does not defeat the surface to interface joint. Interfaces of materials such as Ni-200 can be affixed to metallic surfaces by welding or by brazing with a first braze alloy. The Ni-200 interfaces can then be brazed together using a second braze alloy. The second braze alloy can be chosen so that it minimally alters the properties of the interfaces to allow multiple braze, heat and disassemble, rebraze cycles.

  9. Reversal bending fatigue testing

    DOEpatents

    Wang, Jy-An John; Wang, Hong; Tan, Ting

    2014-10-21

    Embodiments for apparatuses for testing reversal bending fatigue in an elongated beam are disclosed. Embodiments are configured to be coupled to first and second end portions of the beam and to apply a bending moment to the beam and create a pure bending condition in an intermediate portion of the beam. Embodiments are further configured to cyclically alternate the direction of the bending moment applied to the beam such that the intermediate portion of the beam cyclically bends in opposite directions in a pure bending condition.

  10. Unlike quercetin glycosides, cyanidin glycoside in red leaf lettuce responds more sensitively to increasing low radiation intensity before than after head formation has started.

    PubMed

    Becker, Christine; Klaering, Hans-Peter; Schreiner, Monika; Kroh, Lothar W; Krumbein, Angelika

    2014-07-23

    This study investigated the effect of low-level photosynthetic photon flux density (PPFD; 43-230 μmol m(-2) s(-1)) on the major phenolic compounds of red leaf lettuce in three growth stages, before, during, and after head formation, using HPLC-DAD-ESI-MS(2) and evaluating via multiple regression analysis. Generally, the light-related increase of flavonoid glycosides was structure and growth stage-dependent. In detail, an interaction was detected between plant age and PPFD regarding cyanidin-3-O-(6"-O-malonyl)-glucoside concentration: the increase was strongest before head formation. The relationship between PPFD and quercetin-3-O-(6"-O-malonyl)-glucoside concentration was linear, whereas the increase of quercetin-3-O-glucoside and -3-O-glucuronide concentrations abated with increasing PPFD. Independent of growth stage, the caffeic acid derivatives concentration was not related to PPFD. All major phenolic compounds decreased with plant age. These results show the differential regulation of cyanidin, quercetin, and caffeic acid derivatives in lettuce, although closely connected biosynthetically, and emphasize the importance of ontogeny in the study of plant physiology. PMID:24382136

  11. Unlike Quercetin Glycosides, Cyanidin Glycoside in Red Leaf Lettuce Responds More Sensitively to Increasing Low Radiation Intensity before than after Head Formation Has Started

    PubMed Central

    2014-01-01

    This study investigated the effect of low-level photosynthetic photon flux density (PPFD; 43230 ?mol m2 s1) on the major phenolic compounds of red leaf lettuce in three growth stages, before, during, and after head formation, using HPLC-DAD-ESI-MS2 and evaluating via multiple regression analysis. Generally, the light-related increase of flavonoid glycosides was structure and growth stage-dependent. In detail, an interaction was detected between plant age and PPFD regarding cyanidin-3-O-(6?-O-malonyl)-glucoside concentration: the increase was strongest before head formation. The relationship between PPFD and quercetin-3-O-(6?-O-malonyl)-glucoside concentration was linear, whereas the increase of quercetin-3-O-glucoside and -3-O-glucuronide concentrations abated with increasing PPFD. Independent of growth stage, the caffeic acid derivatives concentration was not related to PPFD. All major phenolic compounds decreased with plant age. These results show the differential regulation of cyanidin, quercetin, and caffeic acid derivatives in lettuce, although closely connected biosynthetically, and emphasize the importance of ontogeny in the study of plant physiology. PMID:24382136

  12. 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.

    PubMed

    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. PMID:26042546

  13. Purification and characterization of a glycoside hydrolase family 43 Beta-xylosidase from Geobacillus thermoleovorans IT-08

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The gene encoding a glycoside hydrolase family 43 enzyme termed deAX was isolated and subcloned from a culture seeded with a compost starter mixed bacterium population, expressed with a C-terminal His6-tag, and purified to apparent homogeneity. deAX was monomeric in solution, and had a broad pH maxi...

  14. The influence of the hexopyranose ring geometry on the conformation of glycosidic linkages investigated using molecular dynamics simulations.

    PubMed

    Plazinski, Wojciech; Drach, Mateusz

    2015-10-13

    The conformation of the carbohydrate molecules is a subject of many theoretical and experimental studies. The different timescales associated with the particular degrees of freedom hinder the progress in both those fields. The present paper reports the results of computational studies aimed at elucidating and characterizing the potential correlations between the two main structural determinants of the carbohydrate structure, i.e. the ring conformation and the orientation of the glycosidic bonds (expressed in terms of the ? and ? glycosidic dihedral angles). The free energy landscapes computed for 16 different oligomers composed of unsubstituted, 1,4-linked hexopyranose residues allowed for a detailed insight into how the ring geometry affects the glycosidic linkage conformation. The factor of main importance appeared to be the local changes of the chain length induced by the ring conformational rearrangements. This effect is important mainly for the carbohydrate chains exploiting the glycosidic bonds of uniform orientation with respect to the ring (i.e. either exclusively axially or exclusively equatorially oriented). The shape of the ring may affect the (?,?) free energy maps but only if the population of the alternative ring conformers is relatively high and (at the same time) the presence of such conformers is associated with the significant shifts of the favorable ? and ? values. PMID:26279522

  15. Synthesis of novel 2-deoxy-?-benzyl-C-glycosides by highly stereo- and chemoselective hydrogenation of exo-glycals.

    PubMed

    Daz, Gisela; Ponzinibbio, Agustn; Bravo, Rodolfo Daniel

    2014-07-01

    Novel 2-deoxy-?-benzyl-C-glycosides were prepared in good yields and excellent stereoselectivity by a route involving the Wittig reaction of glycosyl phosphonium salts and reduction of exo-glycals as key steps. Hydrogenation of benzyl protected enol ethers was performed with Pd/C(en) as an effective chemoselective catalyst to afford exclusively ? anomers. PMID:24887703

  16. Direct determination of protonation states and visualization of hydrogen bonding in a glycoside hydrolase with neutron crystallography.

    PubMed

    Wan, Qun; Parks, Jerry M; Hanson, B Leif; Fisher, Suzanne Zoe; Ostermann, Andreas; Schrader, Tobias E; Graham, David E; Coates, Leighton; Langan, Paul; Kovalevsky, Andrey

    2015-10-01

    Glycoside hydrolase (GH) enzymes apply acid/base chemistry to catalyze the decomposition of complex carbohydrates. These ubiquitous enzymes accept protons from solvent and donate them to substrates at close to neutral pH by modulating the pKa values of key side chains during catalysis. However, it is not known how the catalytic acid residue acquires a proton and transfers it efficiently to the substrate. To better understand GH chemistry, we used macromolecular neutron crystallography to directly determine protonation and ionization states of the active site residues of a family 11 GH at multiple pD (pD=pH+0.4) values. The general acid glutamate (Glu) cycles between two conformations, upward and downward, but is protonated only in the downward orientation. We performed continuum electrostatics calculations to estimate the pKa values of the catalytic Glu residues in both the apo- and substrate-bound states of the enzyme. The calculated pKa of the Glu increases substantially when the side chain moves down. The energy barrier required to rotate the catalytic Glu residue back to the upward conformation, where it can protonate the glycosidic oxygen of the substrate, is 4.3 kcal/mol according to free energy simulations. These findings shed light on the initial stage of the glycoside hydrolysis reaction in which molecular motion enables the general acid catalyst to obtain a proton from the bulk solvent and deliver it to the glycosidic oxygen. PMID:26392527

  17. A general approach to quantification of hydroxycinnamic acid derivatives and flavones, flavonols, and their glycosides by UV spectrophotometry

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  18. Validation of HPLC-UV method for determination of minor glycosides contained in Stevia rebaudiana Bertoni leaves.

    PubMed

    Aranda-Gonzlez, Irma; Moguel-Ordoez, Yolanda; Betancur-Ancona, David

    2015-05-01

    Leaves of Stevia rebaudiana contain glycosides with sweetness and biological activity. However besides the major glycosides, there are other glycosides within extracts that may contribute to its activity, and therefore it is important to quantify them. In this work, an isocratic HPLC method was validated for determination of dulcoside A, steviolbioside, rebaudioside C and rebaudioside B. An HPLC method was performed using a C18 column (250??4.6?mm, particle size 5?m) and a UV detector set at 210?nm. The mobile phase consisted of a 32:68 (v/v) mixture of acetonitrile and sodium phosphate buffer (10?mmol/L, pH?2.6), set to a flow rate of 1.0?mL/min. The calculated parameters were: sensitivity, linearity, limit of detection (LOD), limit of quantification (LOQ), accuracy and precision. The calibration curves were linear over the working range 25-150?g/mL, with coefficient of correlation of ?0.99 and coefficient of determination of ?0.98. The LOD was 5.68-8.81?g/mL, while the LOQ was 17.21-26.69?g/mL. The percentage recoveries of fortified samples were 100??10% and precision, relative standard deviation, was <10%. The method validation showed accuracy, linearity and precision; therefore this method can be applied for quantitative analysis of minor steviol glycosides in S. rebaudiana leaves. PMID:25296637

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  20. INFLUENCE OF GLYCOSIDIC LINKAGES AND MOLECULAR WEIGHT ON THE FERMENTATION OF MALTOSE-BASED OLIGOSACCHARIDES BY GUT BACTERIA

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A structure-function study was carried out to increase knowledge of how glycosidic linkages and molecular weight of carbohydrates contribute towards the selectivity of fermentation by gut bacteria. Oligosaccharides with maltose as the common carbohydrate source were used. Potentially prebiotic alt...

  1. Three unusual 22-beta-O-23-hydroxy-(5 alpha)-spirostanol glycosides from the fruits of Solanum torvum.

    PubMed

    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. PMID:16141580

  2. Determination of flavonol glycosides in green tea, oolong tea and black tea by UHPLC compared to HPLC.

    PubMed

    Jiang, Heyuan; Engelhardt, Ulrich H; Thrne, 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. PMID:25863606

  3. Cyanuric Chloride as an Efficient Catalyst for the Synthesis of 2,3-Unsaturated O-Glycosides by Ferrier Rearrangement

    PubMed Central

    Yang, Xiaojuan; Li, Na

    2014-01-01

    Cyanuric chloride has been found to be an efficient catalyst for the synthesis of 2,3-unsaturated O-glycosides from the reaction of 3,4,6-tri-O-acetyl-D-glucal and a wide range of alcohols in dichloromethane at room temperature. The experimental procedure is simple, and the products are obtained in high yields. PMID:24574881

  4. Evaluation of anti-HIV-1 activity of a new iridoid glycoside isolated from Avicenna marina, in vitro.

    PubMed

    Behbahani, Mandana

    2014-11-01

    This study was carried out to check the efficacy of methanol seed extract of Avicenna marina and its column chromatographic fractions on Peripheral Blood Mono nuclear Cells (PBMCs) toxicity and HIV-1 replication. The anti-HIV-1 activities of crude methanol extract and its fractions were performed by use of real-time polymerase chain reaction (PCR) assay and HIV-1 p24 antigen kit. A time of drug addiction approach was also done to identify target of anti-HIV compound. The activity of the extracts on CD4, CD3, CD19 and CD45 expression in lymphocytes population was performed by use of flow cytometry. The most active anti-HIV agent was detected by spectroscopic analysis as 2'-O-(4-methoxycinnamoyl) mussaenosidic acid. The apparent effective concentrations for 50% virus replication (EC50) of methanol extract and iridoid glycoside were 45 and 0.1 ?g/ml respectively. The iridoid glycoside also did not have any observable effect on the proportion of CD4, CD3, CD19 and CD45 cells or on the intensity of their expressions on PBMCs. In addition, the expression level of C-C chemokine receptor type 5 (CCR5) and chemokine receptor type 4 (CXCR4) on CD4(+) T cells were decreased in cells treated with this iridoid glycoside. The reduction of these two HIV coreceptors and the result of time of addition study demonstrated that this iridoid glycoside restricts HIV-1 replication on the early stage of HIV infection. PMID:25239814

  5. Palladium(0)-catalysed synthesis of 2,3- and 3,4-unsaturated aryl ?-O-glycosides.

    PubMed

    Kubiak, Agnieszka; Ko?odziuk, Robert; Porwa?ski, Stanis?aw; Zawisza, Anna

    2015-11-19

    Arylation of 6-O-tert-butyldiphenylsilyl-3,4-di-O-isobutyloxycarbonyl-d-glucal (3) with various phenols in the presence of a catalytic amount of palladium(0) gave the corresponding 2,3- and 3,4-unsaturated ?-O-glycosides. The reaction is stereospecific, in all cases, only the ?-anomer is formed. PMID:26406453

  6. Reverse engineering molecular hypergraphs.

    PubMed

    Rahman, Ahsanur; Poirel, Christopher L; Badger, David J; Estep, Craig; Murali, T M

    2013-01-01

    Analysis of molecular interaction networks is pervasive in systems biology. This research relies almost entirely on graphs for modeling interactions. However, edges in graphs cannot represent multiway interactions among molecules, which occur very often within cells. Hypergraphs may be better representations for networks having such interactions, since hyperedges can naturally represent relationships among multiple molecules. Here, we propose using hypergraphs to capture the uncertainty inherent in reverse engineering gene-gene networks. Some subsets of nodes may induce highly varying subgraphs across an ensemble of networks inferred by a reverse engineering algorithm. We provide a novel formulation of hyperedges to capture this uncertainty in network topology. We propose a clustering-based approach to discover hyperedges. We show that our approach can recover hyperedges planted in synthetic data sets with high precision and recall, even for moderate amount of noise. We apply our techniques to a data set of pathways inferred from genetic interaction data in S. cerevisiae related to the unfolded protein response. Our approach discovers several hyperedges that capture the uncertain connectivity of genes in relevant protein complexes, suggesting that further experiments may be required to precisely discern their interaction patterns. We also show that these complexes are not discovered by an algorithm that computes frequent and dense subgraphs. PMID:24384702

  7. Reverse Engineering Molecular Hypergraphs

    PubMed Central

    Rahman, Ahsanur; Poirel, Christopher L.; Badger, David J.; Estep, Craig; Murali, T.M.

    2014-01-01

    Analysis of molecular interaction networks is pervasive in systems biology. This research relies almost entirely on graphs for modeling interactions. However, edges in graphs cannot represent multiway interactions among molecules, which occur very often within cells. Hypergraphs may be better representations for networks having such interactions, since hyperedges can naturally represent relationships among multiple molecules. Here, we propose using hypergraphs to capture the uncertainty inherent in reverse engineering gene-gene networks. Some subsets of nodes may induce highly varying subgraphs across an ensemble of networks inferred by a reverse engineering algorithm. We provide a novel formulation of hyperedges to capture this uncertainty in network topology. We propose a clustering-based approach to discover hyperedges. We show that our approach can recover hyperedges planted in synthetic data sets with high precision and recall, even for moderate amount of noise. We apply our techniques to a data set of pathways inferred from genetic interaction data in S. cerevisiae related to the unfolded protein response. Our approach discovers several hyperedges that capture the uncertain connectivity of genes in relevant protein complexes, suggesting that further experiments may be required to precisely discern their interaction patterns. We also show that these complexes are not discovered by an algorithm that computes frequent and dense subgraphs. PMID:24384702

  8. Reverse Quantum Waves

    NASA Astrophysics Data System (ADS)

    Boyd, Jeffrey

    2010-02-01

    As preposterous as it might sound, if quantum waves travel in the reverse direction from subatomic particles, then most of quantum physics can be explained without quantum weirdness or Schr"odinger's cat. Quantum mathematics is unchanged. The diffraction pattern on the screen of the double slit experiment is the same. This proposal is not refuted by the Innsbruck experiments; this is NOT a hidden local variable theory. Research evidence will be presented that is consistent with the idea waves travel in the opposite direction as neutrons. If one's thinking shifts from forwards to backwards quantum waves, the world changes so drastically it is almost unimaginable. Quantum waves move from the mathematical to the real world, multiply in number, and reverse in direction. Wave-particle duality is undone. In the double slit experiment every part of the target screen is emitting such quantum waves in all directions. Some pass through the two slits. Interference occurs on the opposite side of the barrier than is usually imagined. They impinge on ``S'' and an electron is released at random. Because of the interference it is more likely to follow some waves than others. It follows one and only one wave backward; hitting the screen where it's wave originated. )

  9. Glycosidic Bond Cleavage in DNA Nucleosides: Effect of Nucleobase Damage and Activation on the Mechanism and Barrier.

    PubMed

    Lenz, Stefan A P; Kellie, Jennifer L; Wetmore, Stacey D

    2015-12-24

    Although DNA damage can have a variety of deleterious effects on cells (e.g., senescence, death, and rapid growth), the base excision repair (BER) pathway combats the effects by removing several types of damaged DNA. Since the first BER step involves cleavage of the bond between the damaged nucleobase and the DNA sugar-phosphate backbone, we have used density functional theory to compare the intrinsic stability of the glycosidic bond in a number of common DNA oxidation, deamination, and alkylation products to the corresponding natural nucleosides. Our calculations predict that the dissociative (SN1) and associative (SN2) pathways are nearly isoenergetic, with the dissociative pathway only slightly favored on the Gibbs reaction surface for all canonical and damaged nucleosides, which suggests that DNA damage does not affect the inherently most favorable deglycosylation pathway. More importantly, with the exception of thymine glycol, all DNA lesions exhibit reduced glycosidic bond stability relative to the undamaged nucleosides. Furthermore, the trend in the magnitude of the deglycosylation barrier reduction directly correlates with the relative nucleobase acidity (at N9 for purines or N1 for pyrimidines), which thereby provides a computationally efficient, qualitative measure of the glycosidic bond stability in DNA damage. The effect of nucleobase activation (protonation) at different sites predicts that the positions leading to the largest reductions in the deglycosylation barrier are typically used by DNA glycosylases to facilitate base excision. Finally, deaza purine derivatives are found to have greater glycosidic bond stability than the canonical counterparts, which suggests that alterations to excision rates measured using these derivatives to probe DNA glycosylase function must be interpreted in reference to the inherent differences in the nucleoside reactivity. Combined with previous studies of the deglycosylation of DNA nucleosides, the current study provides a greater fundamental understanding about the reactivity of the glycosidic bond in damaged DNA, which has direct implications to the function of critical DNA repair enzymes. PMID:26618397

  10. [Comparative analysis of the cardiac glycosides action on the growth of the cardiac tissue explants].

    PubMed

    Lopatina, E V; Penniia?nen, V A; Tsyrlin, V A

    2005-11-01

    The method of organotypical cell culture was used. The long-term cell culture of cardiac embryonic tissue of 10-12-days old chicken was investigated. The effects of ouabaine, strophantin K and digoxin on the growth of cardiac tissue explant were measured. The ouabain concentration which stimulates activity of Na+, K+-ATPase as the signal transducer, was determined. It was equal to 10(-10) M. Strophantin K and digoxin stimulate growth of cardiac tissue in concentration equal to 10(-16) M and 10(-18) M, resp. The data obtained show that application of cardiac glycosides led to control of cardiac tissue growth in dose-dependent manner. We hypothesize that alpha3 isoform of Na+, K+-ATPase is a signal transducer that controls the cardiac cell metabolism and growth. PMID:16408638

  11. Nizwaside: a new anticancer pregnane glycoside from the sap of Desmidorchis flava.

    PubMed

    Hussain, Hidayat; Raees, Muhammad Adil; Rehman, Najeeb Ur; Al-Rawahi, Ahmed; Csuk, René; Khan, Husain Yar; Abbas, Ghulam; Al-Broumi, Mohammed Abdullah; Green, Ivan R; Elyassi, Ali; Mahmood, Talat; Al-Harrasi, Ahmed

    2015-12-01

    The sap from the succulent Desmidorchis flava (N.E.Br) Meve and Liede yielded a new pregnane glycoside, named nizwaside whose structure was established using 1D and 2D NMR techniques as well as mass spectrometry (ESIMS). Nizwaside was tested for anticancer, DPPH antioxidant, urease enzyme inhibition, α-glucosidase enzyme inhibition and acetylcholinesterase inhibition activities. Interestingly, nizwaside showed significant anti-proliferative effects on MDA MB231 breast cancer cells with an IC(50) of 23.5 µg/ml. Moreover, nizwaside was more effective than Doxorubicin, a well-known clinical anticancer drug, in suppressing MDA MB231 cell proliferation even at concentrations lower than that of Doxorubicin (75 µg/ml nizwaside vs. 100 µg/ml Doxorubicin). On the other hand, nizwaside showed relatively weak antioxidant activity with 15 % inhibition. PMID:26335549

  12. Suncheonosides A-D, Benzothioate Glycosides from a Marine-Derived Streptomyces sp.

    PubMed

    Shin, Bora; Ahn, Seyeon; Noh, Minsoo; Shin, Jongheon; Oh, Dong-Chan

    2015-06-26

    A marine-derived Streptomyces strain, SSC21, was isolated from the sediment of Suncheon Bay, Republic of Korea. Chemical analysis of the bacterial strain resulted in the isolation of four new metabolites, suncheonosides A-D (1-4, respectively), each bearing a sulfur atom. The planar structures of the suncheonosides were identified as hexasubstituted benzothioate glycosides by combined spectroscopic analyses. Analysis of the configuration of the sugar moieties based on ROESY nuclear magnetic resonance correlations, one-bond (1)H-(13)C coupling constant analysis, and chemical derivatizations indicated that the suncheonosides incorporate only l-rhamnose. Suncheonosides A, B, and D promoted adiponectin production in a concentration-dependent manner during adipogenesis in human mesenchymal stem cells, suggesting antidiabetic potential. PMID:26078114

  13. Structure of Acidothermus cellulolyticus family 74 glycoside hydrolase at 1.82 resolution.

    PubMed

    Alahuhta, Markus; Adney, William S; Himmel, Michael E; Lunin, Vladimir V

    2013-12-01

    Here, a 1.82? resolution X-ray structure of a glycoside hydrolase family 74 (GH74) enzyme from Acidothermus cellulolyticus is reported. The resulting structure was refined to an R factor of 0.150 and an Rfree of 0.196. Structural analysis shows that five related structures have been reported with a secondary-structure similarity of between 75 and 89%. The five similar structures were all either Clostridium thermocellum or Geotrichum sp. M128 GH74 xyloglucanases. Structural analysis indicates that the A. cellulolyticus GH74 enzyme is an endoxyloglucanase, as it lacks a characteristic loop that blocks one end of the active site in exoxyloglucanases. Superimposition with the C.thermocellum GH74 shows that Asp451 and Asp38 are the catalytic residues. PMID:24316824

  14. Chitosanases from Family 46 of Glycoside Hydrolases: From Proteins to Phenotypes

    PubMed Central

    Viens, Pascal; Lacombe-Harvey, Marie-Ève; Brzezinski, Ryszard

    2015-01-01

    Chitosanases, enzymes that catalyze the endo-hydrolysis of glycolytic links in chitosan, are the subject of numerous studies as biotechnological tools to generate low molecular weight chitosan (LMWC) or chitosan oligosaccharides (CHOS) from native, high molecular weight chitosan. Glycoside hydrolases belonging to family GH46 are among the best-studied chitosanases, with four crystallography-derived structures available and more than forty enzymes studied at the biochemical level. They were also subjected to numerous site-directed mutagenesis studies, unraveling the molecular mechanisms of hydrolysis. This review is focused on the taxonomic distribution of GH46 proteins, their multi-modular character, the structure-function relationships and their biological functions in the host organisms. PMID:26516868

  15. New Ent-Kaurane-Type Diterpene Glycosides and Benzophenone from Ranunculus muricatus Linn.

    PubMed

    Wu, Bi-Ling; Zou, Hui-Liang; Qin, Fang-Min; Li, Hong-Yu; Zhou, Guang-Xiong

    2015-01-01

    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. PMID:26694331

  16. Chitosanases from Family 46 of Glycoside Hydrolases: From Proteins to Phenotypes.

    PubMed

    Viens, Pascal; Lacombe-Harvey, Marie-ve; Brzezinski, Ryszard

    2015-11-01

    Chitosanases, enzymes that catalyze the endo-hydrolysis of glycolytic links in chitosan, are the subject of numerous studies as biotechnological tools to generate low molecular weight chitosan (LMWC) or chitosan oligosaccharides (CHOS) from native, high molecular weight chitosan. Glycoside hydrolases belonging to family GH46 are among the best-studied chitosanases, with four crystallography-derived structures available and more than forty enzymes studied at the biochemical level. They were also subjected to numerous site-directed mutagenesis studies, unraveling the molecular mechanisms of hydrolysis. This review is focused on the taxonomic distribution of GH46 proteins, their multi-modular character, the structure-function relationships and their biological functions in the host organisms. PMID:26516868

  17. A triterpene glycoside from black cohosh that inhibits osteoclastogenesis by modulating RANKL and TNFalpha signaling pathways.

    PubMed

    Qiu, Samuel X; Dan, Chun; Ding, Li-Sheng; Peng, Shulin; Chen, Shao-Nong; Farnsworth, Norman R; Nolta, Jan; Gross, Michael L; Zhou, Ping

    2007-07-01

    Osteoporosis is a major age-related source of morbidity and mortality. Increased bone resorption mediated by osteoclasts is central to its pathogenesis. Cytokines, particularly RANKL and TNFalpha, are often increased under pathologic conditions, leading to enhanced osteoclastogenesis. Black cohosh (Actaea/Cimicifuga racemosa L), a popular herbal supplement for the treatment of menopausal symptoms, was recently shown to have the beneficial effect of preventing bone loss. Here, we demonstrate that 25-acetylcimigenol xylopyranoside (ACCX), a triterpenoid glycoside isolated from black cohosh, potently blocks in vitro osteoclastogenesis induced by either RANKL or TNFalpha. This blockage of osteoclastogenesis elicited by ACCX results from abrogation of the NF-kappaB and ERK pathways induced by either RANKL or TNFalpha, respectively. Importantly, this compound attenuates TNFalpha-induced bone loss in vivo. Therefore, ACCX represents a potential lead for the development of a new class of antiosteoporosis agents. PMID:17656322

  18. Evaluation of a silicon oxynitride hydrophilic interaction liquid chromatography column in saccharide and glycoside separations.

    PubMed

    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. PMID:25631584

  19. Synthesis of 3-aminopropyl glycosides of linear ?-(1?3)-d-glucooligosaccharides.

    PubMed

    Yashunsky, Dmitry V; Tsvetkov, Yury E; Grachev, Alexey A; Chizhov, Alexander O; Nifantiev, Nikolay E

    2016-01-01

    3-Aminopropyl glycosides of a series of linear ?-(1?3)-linked d-glucooligosaccharides containing from 3 to 13 monosaccharide units were efficiently prepared. The synthetic scheme featured highly regioselective glycosylation of 4,6-O-benzylidene-protected 2,3-diol glycosyl acceptors with a disaccharide thioglycoside donor bearing chloroacetyl groups at O-2' and -3' as a temporary protection of the diol system. Iteration of the deprotection and glycosylation steps afforded the series of the title oligoglucosides differing in length by two monosaccharide units. A novel procedure for selective removal of acetyl groups in the presence of benzoyl ones consisting in a brief treatment with a large excess of hydrazine hydrate has been proposed. PMID:26595660

  20. Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis.

    PubMed

    Szabó, Lajos Z; Hanrahan, Dillon J; Jones, Evan M; Martin, Erin; Pemberton, Jeanne E; Polt, Robin

    2016-03-01

    Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data ((1)H and (13)C, including COSY, HSQC and HMBC) are reported for compounds not previously described. PMID:26795078