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1

Determination of bioactive nitrile glycoside(s) in drumstick ( Moringa oleifera) by reverse phase HPLC  

Microsoft Academic Search

A high-performance liquid chromatographic method for the determination of novel bioactive nitrile glycosides niaziridin and niazirin in the leaves, pods and bark of Moringa oleifera is reported. Niaziridin is a bioenhancer for drugs and nutrients. The analytical conditions for reversed-phase HPLC with UV detection were as follows: column, Chromolith RP-18e, 4.6×100mm 0.5?m (Merck); column temperature, 25°C; mobile phase, a 20:80

Karuna Shanker; Madan M. Gupta; Santosh K. Srivastava; Dnyaneshwar U. Bawankule; Anirban Pal; Suman P. S. Khanuja

2007-01-01

2

Determination of Saponin Glycosides in Bacopa monnieri by Reversed Phase High Performance Liquid Chromatography  

Microsoft Academic Search

A reversed phase HPLC system was developed for the quantitative analysis of bioactive saponin glycosides in the medicinal plant, Bacopa monnieri (L.) Wettst (Brahmi). Five dammarane saponin glycosides namely Bacoside A 3 ( 1), Bacopaside II ( 2), 3-O-(?-L-arabinofuranosyl(1 2)-{?-D-glucopyranosyl-(1 3)}-?-L-arabinopyranosyl) jujubogenin ( 3), Bacopasaponin C (4) and Bacopaside I (5) were analyzed on a C-18 column. With an isocratic

Watoo Phrompittayarat; Sakchai Wittaya-areekul; Kanchalee Jetiyanon; Waraporn Putalun; Hiroyuki Tanaka; Kornkanok Ingkaninan

3

Transport of glycosides through liquid organic membranes mediated by reversible boronate formation is a diffusion-controlled process  

Microsoft Academic Search

The ability of phenylboronic acid, [3-(1-adamantylcarboxamido)phenyl]boronic acid, and diphenylborinic acid to extract and transport p-nitrophenyl [beta]-D-glucopyranoside (glucoside), p-nitrophenyl [beta]-D-galactopyranoside (galactoside), and p-nitrophenyl [beta]-D-mannopyranoside (mannoside) through a liquid organic membrane, in the presence of trioctylmethylammonium or tetrabutylammonium chloride, was determined. Under the conditions examined, glycoside transport was facilitated by the reversible formation of covalent tetrahedral, anionic glycoside-boronate complexes, which partitioned into

Gregory T. Morin; Martin Patrick Hughes; Marie-France Paugam; Bradley D. Smith

1994-01-01

4

Independent domestications of cultivated tree peonies from different wild peony species.  

PubMed

An understanding of plant domestication history provides insights into general mechanisms of plant adaptation and diversification and can guide breeding programmes that aim to improve cultivated species. Cultivated tree peonies (genus Paeonia L.) are among the most popular ornamental plants in the world; yet, the history of their domestication is still unresolved. Here, we explored whether the domestication in China of historically cultivated peonies, that is, the common and flare cultivated tree peonies, was a single event or whether independent domestications occurred. We used 14 nuclear microsatellite markers and a comprehensive set of 553 tree peonies collected across China, including common tree peonies, flare tree peonies and the wild species or subspecies that are potential contributors to the cultivated tree peonies, that is, Paeonia rockii ssp. rockii, P. rockii ssp. atava, P. jishanensis and P. decomposita. Assignment methods, a principal component analysis and approximate Bayesian computations provided clear evidence for independent domestications of these common tree and flare tree peonies from two distinct and allopatric wild species, P. jishanensis and P. rockii ssp. atava, respectively. This study provides the first example of independent domestications of cultivated trees from distinct species and locations. This work also yields crucial insight into the history of domestication of one of the most popular woody ornamental plants. The cultivated peonies represent an interesting case of parallel and convergent evolution. The information obtained in this study will be valuable both for improving current tree peony breeding strategies and for understanding the mechanisms of domestication, diversification and adaptation in plants. PMID:24138195

Yuan, Jun-Hui; Cornille, Amandine; Giraud, Tatiana; Cheng, Fang-Yun; Hu, Yong-Hong

2014-01-01

5

Reversal of multidrug resistance by morning glory resin glycosides in human breast cancer cells.  

PubMed

Reversal of multidrug resistance (MDR) by thirty resin glycosides from the morning glory family (Convolvulaceae) was evaluated in vinblastine-resistant human breast carcinoma cells (MCF-7/Vin). The effects of these amphipathic compounds on the cytotoxicity and P-glycoprotein (P-gp)-mediated MDR were estimated with the sulforhodamine B colorimetric assay. Active noncytotoxic compounds exerted a potentiation effect of vinblastine susceptibility by 1- to over 1906-fold at tested concentrations of 5 and 25 ?g/mL. Murucoidin V (1) enhanced vinblastine activity 255-fold when incorporated at 25 ?g/mL and also, based on flow cytometry, significantly increased the intracellular accumulation of rhodamine 123 with the use of reserpine as a positive control for a MDR reversal agent. Incubation of MCF-7/Vin cells with 1 caused an increase in uptake and notably lowered the efflux rate of rhodamine 123. Decreased expression of P-glycoprotein by compound 1 was detected by immunofluorescence flow cytometry after incubation with an anti-P-gp monoclonal antibody. These results suggest that resin glycosides represent potential efflux pump inhibitors for overcoming MDR in cancer therapy. PMID:22148475

Figueroa-González, Gabriela; Jacobo-Herrera, Nadia; Zentella-Dehesa, Alejandro; Pereda-Miranda, Rogelio

2012-01-27

6

Heart-cutting two-dimensional (size exclusion x reversed phase) liquid chromatography-mass spectrometry analysis of flavonol glycosides from leaves of Maytenus ilicifolia.  

PubMed

Two-dimensional liquid chromatography-electrospray ionization mass spectrometry was employed to analyze flavonol glycosides present in leaves of Maytenus ilicifolia, frequently used in traditional Brazilian medicine. Since they contain many flavonol glycosides, including isomers, one-dimensional liquid chromatography did not give complete separation and identification, yielding overlapping of compounds with different molecular weights. Thus, employing size exclusion chromatography in the first and reversed phase in the second dimension, a great number of flavonol glycosides could be identified and its relative abundances determined. The majority of glycosides contained kaempferol or quercetin as aglycones, and glycosides with previously unreported structures were also present and characterized. PMID:19062030

de Souza, Lauro M; Cipriani, Thales R; Sant'ana, Carolina F; Iacomini, Marcello; Gorin, Philip A J; Sassaki, Guilherme L

2009-01-01

7

'Peony Nebula' Star Settles for Silver Medal  

NASA Technical Reports Server (NTRS)

[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.

2008-01-01

8

Optimum harvesting time of herbaceous peony buds for cutting flowers  

Microsoft Academic Search

The herbaceous peony is one of the cut flowers that has become increasingly popular in the international market in recent\\u000a years. In the study, 11 cultivars of herbaceous peonies suitable for cutting flowers were selected; different harvesting stages\\u000a (three or four stages) were identified according to bud development observation (bud firmness, bud diameter, sepal angle,\\u000a petal angle, and color showing).

Xiao-nan Yu; Peng-peng Guo; Guang-pei Lu; Qi-xiang Zhang

2011-01-01

9

Pharmacokinetic Studies of the Significance of Herbaceous Compatibility of Peony Liquorice Decoction  

Microsoft Academic Search

This study aimed to explore the rationality of herbaceous compatibility of peony liquorice decoction by analyzing the pharmacokinetic parameters of peoniflorin and glycyrrhetinic acid in SD rats' plasma. A HPLC\\/MS\\/MS method was used to detect the concentrations of peoniflorin and glycyrrhetinic acid in plasma of SD rats which were administrated with peony, liquorice and peony liquorice decoction, respecttively. Compared with

Wang Wenping; Wang Chuijie; Gu Song; Cao Qichen; Lv Yuping; Gao Jingjing; Wang Shujing

2009-01-01

10

Development and validation of a reversed-phase high-performance liquid chromatography method for routine identification and purity assessment of high-purity steviol glycoside sweeteners.  

PubMed

The widespread application of stevia-based sweeteners in food products has resulted in the need for reliable analytical methods for measuring the purity and identity of high-purity steviol glycoside ingredients. The objective of this research was to develop and validate a new reversed-phase separation method capable of separating and quantifying nine steviol glycosides present in typical high-purity stevia extract ingredients. Results of the study established the linearity of the method at a correlation factor of 1.000 for the two major components and other minor components of this food ingredient. Method accuracy values were in the range of 99.1-100.9%. The percent relative standard deviation for six independent assay determinations was 1.0%. The method was determined to be robust for minor changes in column temperature, initial acetonitrile content, flow rate, and wavelength. The validated high-performance liquid chromatography method was found to be suitable to be included by USP as a Food Chemicals Codex compendial standard for steviol glycosides. PMID:24443893

Bililign, Tsion; Moore, Jeffrey C; Tan, Shane; Leeks, Allan T

2014-02-12

11

In vitro Culture Of Tree Peony Through Axillary Budding  

Microsoft Academic Search

Tree peonies are flowering shrubs which grow from 1 to 6 feet tall and are divided into two main groups: the hybrid and the\\u000a non hybrid group. The latter ones are varieties of P. suffruticosa, comprising more than 500 cultivars. P. suffruticosa cultivars are used as outside ornamentals and as pot plants. Their cultivation under warmer climates, where the flowering

M. Beruto; P. Curir

12

PEONIES FOR FIELD CUT FLOWER PRODUCTION FIRST-YEAR GROWTH  

Microsoft Academic Search

Cultivar trials with herbaceous peonies were initiated during the summer of 2001 to evaluate their potential as fi eld-grown cut fl owers. The plants became well established, and all but three cultivars bloomed in 2002.The bloom times for all cultivars ranged from 30 June through the fi rst week of August (Holloway of this report is to present evaluations of

Patricia S. Holloway; Janice T. Hanscom; Grant E. M. Matheke

13

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

PubMed

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

Xue, Dong; Huang, Xiangdong

2013-10-01

14

Temperature requirements for floral development of herbaceous peony cv. ‘Sarah Bernhardt’  

Microsoft Academic Search

The temperature requirements of peony during the various stages of its annual growing cycle were studied with the ultimate aim of enhancing early forcing and improving profitability. The immediate objective was to study the effects of chilling and subsequent growth conditions on plant development and flowering of ‘Sarah Bernhardt’, one of the most popular cultivars of herbaceous peony. Under our

Rina Kamenetsky; Amalia Barzilay; Amnon Erez; Abraham H Halevy

2003-01-01

15

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

PubMed Central

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.

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

2013-01-01

16

Speciation through homoploid hybridization between allotetraploids in peonies (Paeonia)  

PubMed Central

Phylogenies of Adh1 and Adh2 genes suggest that a widespread Mediterranean peony, Paeonia officinalis, is a homoploid hybrid species between two allotetraploid species, Paeonia peregrina and a member of the Paeonia arietina species group. Three phylogenetically distinct types of Adh sequences have been identified from both accessions of P. officinalis, of which two types are most closely related to the two homoeologous Adh loci of the P. arietina group and the remaining type came from one of the two Adh homoeologs of P. peregrina. The other Adh homoeolog of P. peregrina was apparently lost from the hybrid genome, possibly through backcrossing with the P. arietina group. This is a documentation of homoploid hybrid speciation between allotetraploid species in nature. This study suggests that hybrid speciation between allotetraploids can occur without an intermediate stage of genome diploidization or a further doubling of genome size.

Ferguson, Diane; Sang, Tao

2001-01-01

17

Microsatellite markers in the tree peony, Paeonia suffruticosa (Paeoniaceae).  

PubMed

• Premise of the study: Microsatellite primers were developed in the tree peony, Paeonia suffruticosa, to perform paternity tests as well as assignment to variety in special Austrian collections. • Methods and Results: Using SSR-enriched libraries and EST-mining, 8 polymorphic primer sets were identified in Austrian collections of Paeonia sect. Moutan DC. The primers amplified di- and trinucleotide repeats with 2-6 alleles per locus. All primers also amplified in P. ostii, P. pontaninii var. trolloides, P. delavayi, and P. lutea, and in the herbaceous species P. peregrina and P. tenuifolia (Paeonia sect. Paeon). • Conclusions: These results show the usefulness of primers in P. suffruticosa for population genetic studies and their ability to cross amplify in related taxa across the genus. PMID:21622456

Homolka, Andreas; Berenyi, Maria; Burg, Kornel; Kopecky, Dieter; Fluch, Silvia

2010-06-01

18

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

Federal Register 2010, 2011, 2012, 2013

...the Peony, Pole Pick, and Frank Burge Seed Orchards; Washington AGENCY: Bureau of...the integrity and functionality of the seed orchards, along with the investment of...the Peony, Pole Pick, and Frank Burge Seed Orchards. The withdrawal created by...

2010-10-26

19

Cryopreservation of somatic embryos of the herbaceous peony ( Paeonia lactiflora Pall.) by air drying  

Microsoft Academic Search

This study was carried out to establish a suitable method for the cryopreservation of somatic embryos of the herbaceous peony. The somatic embryos were obtained from cotyledon and anther cultures on a MS medium supplemented with abscisic acid (ABA) and phenylacetic acid (PAA), respectively. The frequency of somatic embryo formation was the greatest (61%) from the cotyledons cultured on a

Hyun Mi Kim; Jong Hee Shin; Jae Keun Sohn

2006-01-01

20

Comparison of shoot induction ability of different explants in herbaceous peony ( Paeonia lactiflora Pall.)  

Microsoft Academic Search

Shoot induction ability of explants of herbaceous peony was investigated in semisolid MS medium containing BA, TDZ and GA3. Callus was readily induced from stem without node and petiole explants within 2 days of culture but failed to generate shoots. Adventitious shoots were successfully produced from meristematic regions only: bud eyes on nodal stem sections, and junctions of petioles and

Daike Tian; Ken M. Tilt; Fenny Dane; Floyd M. Woods; Jeff L. Sibley

2010-01-01

21

Effect of Calcium Sprays on Mechanical Strength and Cell Wall Fractions of Herbaceous Peony (Paeonia Lactiflora Pall.) Inflorescence Stems  

PubMed Central

Calcium is an essential element and imparts significant structural rigidity to the plant cell walls, which provide the main mechanical support to the entire plant. In order to increase the mechanical strength of the inflorescence stems of herbaceous peony, the stems are treated with calcium chloride. The results shows that preharvest sprays with 4% (w/v) calcium chloride three times after bud emergence are the best at strengthening “Da Fugui” peonies’ stems. Calcium sprays increased the concentrations of endogenous calcium, total pectin content as well as cell wall fractions in herbaceous peonies stems, and significantly increased the contents of them in the top segment. Correlation analysis showed that the breaking force of the top segment of peonies’ stems was positively correlated with the ratio of water insoluble pectin to water soluble pectin (R = 0.673) as well as lignin contents (R = 0.926) after calcium applications.

Li, Chengzhong; Tao, Jun; Zhao, Daqiu; You, Chao; Ge, Jintao

2012-01-01

22

Effect of calcium sprays on mechanical strength and cell wall fractions of herbaceous peony (paeonia lactiflora pall.) inflorescence stems.  

PubMed

Calcium is an essential element and imparts significant structural rigidity to the plant cell walls, which provide the main mechanical support to the entire plant. In order to increase the mechanical strength of the inflorescence stems of herbaceous peony, the stems are treated with calcium chloride. The results shows that preharvest sprays with 4% (w/v) calcium chloride three times after bud emergence are the best at strengthening "Da Fugui" peonies' stems. Calcium sprays increased the concentrations of endogenous calcium, total pectin content as well as cell wall fractions in herbaceous peonies stems, and significantly increased the contents of them in the top segment. Correlation analysis showed that the breaking force of the top segment of peonies' stems was positively correlated with the ratio of water insoluble pectin to water soluble pectin (R = 0.673) as well as lignin contents (R = 0.926) after calcium applications. PMID:22606005

Li, Chengzhong; Tao, Jun; Zhao, Daqiu; You, Chao; Ge, Jintao

2012-01-01

23

Vasorelaxant activity of 7-?-O-glycosides biosynthesized from flavonoids.  

PubMed

In this work we report the vasorelaxant activity of 7-?-O-glycosides obtained with biosynthesis of naringenin-7-?-O-glycoside (3) and quercetin-7-?-O-glycoside (4). These compounds were obtained from naringenin (1) and quercetin (2) glycosylation catalyzed by Beauveria bassiana ATCC 7159. Screening of the best strain as a catalyst for glycosylation was carried out and the reaction conditions established. Cultures were grown in PDSM medium for 7 days at 27°C. After purification by reverse-phase preparative HPLC, naringenin-7-?-O-glycoside (3) and quercetin-7-?-O-glycoside (4) were identified by (1)H and (13)C NMR. The right position and ?-configuration of the glucose was determined through HSQC and HMBC experiments. The vasorelaxation potential of naringenin, quercetin and its glycosylated derivatives was evaluated using isolated aorta in vitro models. Interestingly, results suggest that vasorelaxation properties of naringenin, rutin and its glycosides are due to different pathways. PMID:24704375

Penso, Juliana; Cordeiro, Kelly C F A; da Cunha, Carla R M; da Silva Castro, Patricia F; Martins, Daniella R; Liăo, Luciano M; Rocha, Matheus L; de Oliveira, Valéria

2014-06-15

24

Analysis of petal anthocyanins to investigate coloration mechanism in herbaceous peony cultivars  

Microsoft Academic Search

Petal coloration and anthocyanin compositions of 41 herbaceous peony cultivars were analyzed. Anthocyanins were identified by high-performance liquid chromatography–electrospray ionization-mass spectrometry (HPLC–ESI-MSn) coupled with photodiode array detection (DAD). Peonidin-3,5-di-O-glucoside (Pn3G5G), pelargonidin-3,5-di-O-glucoside (Pg3G5G), cyanidin-3,5-di-O-glucoside (Cy3G5G), peonidin-3-O-glucoside (Pn3G), and cyanidin-3-O-glucoside (Cy3G) were the five major anthocyanins in herbaceous peony cultivars. Deep purple or reddish purple cultivars contained 4–5 anthocyanins, whereas pink cultivars

Ni Jia; Qing-Yan Shu; Liang-Sheng Wang; Hui Du; Yan-Jun Xu; Zheng-An Liu

2008-01-01

25

Cryopreservation of somatic embryos of the herbaceous peony (Paeonia lactiflora Pall.) by air drying.  

PubMed

This study was carried out to establish a suitable method for the cryopreservation of somatic embryos of the herbaceous peony. The somatic embryos were obtained from cotyledon and anther cultures on a MS medium supplemented with abscisic acid (ABA) and phenylacetic acid (PAA), respectively. The frequency of somatic embryo formation was the greatest (61%) from the cotyledons cultured on a MS medium supplemented with 1.0 mg l(-1) of ABA. Embryos were also obtained directly from anthers cultured on a MS medium with or without 2.0 mg l(-1) of PAA. For the cryopreservation of peony somatic embryos, the embryos were dried under a stream of sterile air and frozen by immersion in liquid nitrogen. Thawed embryos were germinated into plantlets after placing on a medium containing 0.3 mg l(-1) of gibberellic acid (GA(3)). The frequency of the post-thaw regrowth of cryopreserved somatic embryos was related to their size and desiccation time, the latter ranging from 0 to 2 h. When the somatic embryos were desiccated for 1 h, the frequency of post-thaw regrowth was greater than 66%. The frequency of post-thaw regrowth of the cryopreserved somatic embryos from anthers and cotyledon tissues was generally high when they were 2-3 mm in size. Desiccation may be a suitable method for the cryopreservation of somatic embryos of the herbaceous peony. PMID:16712828

Kim, Hyun Mi; Shin, Jong Hee; Sohn, Jae Keun

2006-08-01

26

Cryopreservation of dormant herbaceous peony (Paeonia lactiflora pall.) shoot-tips by desiccation.  

PubMed

A simplified technique for the cryoprotection of dormant shoot-tips was developed for the germplasm conservation of herbaceous peony (Paeonia lactiflora Pall.). The highest post-thaw regrowth level was obtained from shoot-tips desiccated by air drying for 5 h. The post-thaw regrowth of P. lactiflora. var. 'Mikang' was the highest (74.9 percent) among the five genotypes tested. The regeneration level after cryopreservation was highest (66approximate74%; average of 70 percent) for dormant shoot-tips collected from November to February. Shoot tips which were dissected from non-dormant buds in late March, however, showed very low post-thaw regrowth. Post-thaw regrowth of shoot-tips was promoted in MS medium containing 1 mg 1(-1) of gibberellic acid (GA3) and 0.5 mg 1(-1) of N(6)-benzyladenine (BA). The elongated shoots were rooted on a 1/4 MS medium containing 0.1 mg 1(-1) of beta-naphthalene acetic acid (NAA). In addition, random amplified polymorphic DNAs (RAPDs) assays suggested that the cryostorage treatment used here preserved the genetic fidelity of the peony dormant shoot-tips. This cryopreservation method appears to be promising for the conservation of herbaceous peony germplasm. PMID:17898908

Seo, Mi Jin; Shin, Jong Hee; Sohn, Jae Keun

2007-01-01

27

Plant cyanogenic glycosides  

Microsoft Academic Search

The cyanogenic glycosides belong to the products of secondary metabolism, to the natural products of plants. These compounds are composed of an ?-hydroxynitrile type aglycone and of a sugar moiety (mostly d-glucose). The distribution of the cyanogenic glycosides (CGs) in the plant kingdom is relatively wide, the number of CG-containing taxa is at least 2500, and a lot of such

János Vetter

2000-01-01

28

Glycosides from Stevia rebaudiana  

Microsoft Academic Search

A new laboratory method for isolating the glycosides stevioside and rebaudiosides A and C from leaves of Stevia rebaudiana was proposed. According to HPLC, the glycoside contents in plants grown in Russia (Voronezh Oblast’) and Ukraine (Crimea)\\u000a were 5–6% (stevioside) and 0.3–1.3% (rebaudiosides A and C).

G. I. Kovylyaeva; G. A. Bakaleinik; I. Yu. Strobykina; V. I. Gubskaya; R. R. Sharipova; V. A. Al’fonsov; V. E. Kataev; A. G. Tolstikov

2007-01-01

29

Naturally occurring cardiac glycosides.  

PubMed

Cardiac glycoside poisoning from the ingestion of plants, particularly of oleanders, occurs with reasonable frequency in tropical and subtropical areas. We have assessed a variety of plant specimens for their cardiac glycoside content by means of radioimmunoassays with antibodies that differ in their specificity for cardiac glycosides. Significant amounts of immunoreactive cardiac glycoside were found to be present in the ornamental shrubs: yellow oleander (Thevetia peruviana); oleander (Nerium oleander); wintersweet (Carissa spectabilis); bushman's poison (Carissa acokanthera); sea-mango (Cerbera manghas); and frangipani (Plumeria rubra); and in the milkweeds: redheaded cotton-bush (Asclepias curassavica); balloon cotton (Asclepias fruiticosa); king's crown (Calotropis procera); and rubber vine (Cryptostegia grandifolia). The venom gland of the cane toad (Bufo marinus) also contained large quantities of cardiac glycosides. The competitive immunoassay method permits the rapid screening of specimens that are suspected to contain cardiac glycosides. Awareness of the existence of these plant and animal toxins and their dangers allows them to be avoided and poisoning prevented. The method is also useful for the confirmation of the presence of cardiac glycosides in serum in cases of poisoning. PMID:3086679

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

1986-05-12

30

Bioactive glycosides from Chinese medicines.  

PubMed

Glycosides are the bioactive components of many famous Chinese medicines. Here reported are some bioactive glycosides we discovered from Chinese medicines in recent years. (1) Phenolic glycosides from Chinese medicines: Gastrodia elata, Aconitum austroyunanense and Helicia erratica, three bioactive phenolic glycosides were discovered and two of them have been developed into new drugs. (2) Terpenoidal glycosides: a) Monoterpenoid: the sweroside from Swertia moleensis has been developed into an anti-hepatitis drug; b) Diterpenoid: Phlomis betonicoides contains sweet glycosides; c) Triterpenoid: many biologically active triterpenoid glycosides were isolated from Panax plants and Siraitia grosvenorii. (3) Steroidal glycosides: a) C21-steroid: Cynanchum otophyllum and C. atratrum contain anti-epilepsy and anti-tumor glycosides; b) C27-steroid Hemostatic saponins were found in Paris polyphylla. PMID:1842007

Zhou, J

1991-01-01

31

Herbaceous Peony (Paeonia lactiflora Pall.) as an Alternative Source of Oleanolic and Ursolic Acids.  

PubMed

Oleanolic acid (OA) and ursolic acid (UA) have been proven to possess many biological activities, and much attention is focused on the search for plants which are rich in OA and UA. In this report, the OA and UA accumulation characteristics were investigated in 47 cultivars of Chinese herbaceous peony (Paeonia lactiflora Pall.) and were followed in three cultivars over different developmental stages as measured by high performance liquid chromatography (HPLC). OA and UA levels in leaves and stems demonstrated an overall upward trend from May 1 to September 15 except for UA in the leaves of "Hong Feng". The maximum values of OA and UA in leaves of "Yangfei Chu Yu", "Fen Zhu Pan" and "Hong Feng" were 852.98, 575.60, 290.48 ?g/g FW and 924.94, 827.36, 432.67 ?g/g FW, respectively. The maximum values of OA and UA in stems of "Yangfei Chu Yu", "Fen Zhu Pan" and "Hong Feng" were 359.28, 90.49, 43.90 ?g/g FW and 326.86, 82.25, 56.63 ?g/g FW, respectively. OA and UA contents in leaves of 47 different herbaceous peony cultivars ranged from 66.73-618.12 and 36.23-665.14 ?g/g FW, respectively, with average values of 171.62 and 227.57 ?g/g FW, respectively. The results suggested that the aboveground parts of herbaceous peony may be used as an alternative source of OA and UA for medicinal purposes in addition to its ornamental purposes. PMID:21340006

Zhou, Chunhua; Zhang, Ying; Sheng, Yanle; Zhao, Daqiu; Lv, Sansan; Hu, Yue; Tao, Jun

2011-01-01

32

Herbaceous Peony (Paeonia lactiflora Pall.) as an Alternative Source of Oleanolic and Ursolic Acids  

PubMed Central

Oleanolic acid (OA) and ursolic acid (UA) have been proven to possess many biological activities, and much attention is focused on the search for plants which are rich in OA and UA. In this report, the OA and UA accumulation characteristics were investigated in 47 cultivars of Chinese herbaceous peony (Paeonia lactiflora Pall.) and were followed in three cultivars over different developmental stages as measured by high performance liquid chromatography (HPLC). OA and UA levels in leaves and stems demonstrated an overall upward trend from May 1 to September 15 except for UA in the leaves of “Hong Feng”. The maximum values of OA and UA in leaves of “Yangfei Chu Yu”, “Fen Zhu Pan” and “Hong Feng” were 852.98, 575.60, 290.48 ?g/g FW and 924.94, 827.36, 432.67 ?g/g FW, respectively. The maximum values of OA and UA in stems of “Yangfei Chu Yu”, “Fen Zhu Pan” and “Hong Feng” were 359.28, 90.49, 43.90 ?g/g FW and 326.86, 82.25, 56.63 ?g/g FW, respectively. OA and UA contents in leaves of 47 different herbaceous peony cultivars ranged from 66.73–618.12 and 36.23–665.14 ?g/g FW, respectively, with average values of 171.62 and 227.57 ?g/g FW, respectively. The results suggested that the aboveground parts of herbaceous peony may be used as an alternative source of OA and UA for medicinal purposes in addition to its ornamental purposes.

Zhou, Chunhua; Zhang, Ying; Sheng, Yanle; Zhao, Daqiu; Lv, Sansan; Hu, Yue; Tao, Jun

2011-01-01

33

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

PubMed

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

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

2012-04-15

34

Semisynthetic digoxigenin glycosides  

Microsoft Academic Search

Starting with digoxigenin, L-rhamnose, D-glucose, and D-xylose, the monoglycosides digoxigenin-3-a-L-rhamnopyranoside, 3-ß-D-glycopyranoside, and 3-ß-D-xylopyranoside have been synthesized in approximately 40% yield. The biosides digoxigenin 3,12-di-ß-D-glucopyranoside and 3,12-di-ß-D-xylopyranoside were also obtained in approximately 3% yield. The glycosides obtained possessed high cardiotonic activity.

I. F. Makarevich

1969-01-01

35

Effects of shade on plant growth and flower quality in the herbaceous peony (Paeonia lactiflora Pall.).  

PubMed

Herbaceous peony (Paeonia lactiflora Pall.) is an important ornamental plant used in urban green spaces, but little is known about whether it can grow in a shaded environment or understory. In this study, effects of shade on plant growth and flower quality in the herbaceous peony were investigated. The results showed that P. lactiflora morphology parameters, including plant height, leaf number, stem diameter, branch number, node number and plant crown width, were higher in plants grown with sun exposure compared to those grown in shade; however, opposite trends were observed for the top and middle leaf areas of the plant. Compared with sun exposure, shade decreased P. lactiflora photosynthetic capacity, light saturation point (LSP) and light compensation point (LCP) and increased the apparent quantum yield (AQY), mainly due to declined stomatal conduction (Gs). These decreases caused the soluble sugar, soluble protein and malondialdehyde (MDA) contents to decline, which led to delayed initial flowering date, prolonged flowering time, reduced flower fresh weight, increased flower diameter and faded flower color. Through cloning and expression analysis of anthocyanin biosynthetic genes, we determined that the fading of flower color was the result of reduced anthocyanin content, which was caused by the combined activity of anthocyanin biosynthesis genes and, in particular, of the upstream phenylalanine ammonialyase gene (PlPAL) and chalcone synthase gene (PlCHS). These results could provide us with a theoretical basis for further application of P. lactiflora in the greening of urban spaces and an understanding of the mechanisms behind the changes induced by shade. PMID:23141672

Zhao, Daqiu; Hao, Zhaojun; Tao, Jun

2012-12-01

36

Variants of glycoside hydrolases  

DOEpatents

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.

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

2013-02-26

37

Variants of glycoside hydrolases  

DOEpatents

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.

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

38

Effect of exogenous gibberellic acid, abscisic acid, and benzylaminopurine on epicotyl dormancy of cultured herbaceous peony embryos  

Microsoft Academic Search

Epicotyl dormancy was broken in cultured peony (Paeonia lactiflora Pall.) embryos after topical application of agarose gels containing gibberellic acid, with optimum growth at 1.5 mM gibberellic acid. Addition of 100 µM abscisic acid to the medium resulted in complete inhibition of gibberellic acid-stimulated promotion of dormant epicotyls. Epicotyl dormancy was also broken in embryos by culture on media containing

Julie A. T. Buchheim; Len F. Burkhart; Martin M. Meyer

1994-01-01

39

Pregnane glycosides from Sansevieria trifasciata.  

PubMed

Phytochemical analysis of the whole plant of Sansevieria trifasciata, one of the most common Agavaceae plants, has resulted in the isolation of four new pregnane glycosides. Their structures have been determined by spectroscopic analysis and acid- and alkaline-catalysed hydrolysis to be 1 beta,3 beta-dihydroxypregna-5,16-dien-20-one glycosides. This is believed to be the first report of the isolation of the pregnane glycosides from a plant of the family Agavaceae. PMID:8983214

Mimaki, Y; Inoue, T; Kuroda, M; Sashida, Y

1997-01-01

40

Resin glycosides from Porana duclouxii.  

PubMed

A new intact resin glycoside (3) and two glycosidic acids (1 and 2), all having a common trisaccharide moiety and (11S)-hydroxytetradecanoic acid or (3S,11S)-dihydroxytetradecanoic acid as the aglycone, were obtained from the roots of Porana duclouxii. Their structures were elucidated by spectroscopic analyses and chemical correlations. These compounds represent the first examples of resin glycosides from the genus Porana. PMID:24320876

Ding, Wen-Bing; Zhang, Dai-Gui; Liu, Chun-Jie; Li, Guan-Hua; Li, You-Zhi

2014-01-01

41

Quinoid glycosides from Forsythia suspensa.  

PubMed

Phytochemical investigation on Forsythia suspensa (Thunb.) Vahl afforded 10 compounds, including quinoid glycosides, lignan glycosides, phenylethanoid glycoside and allylbenzene glycoside together with 13 known ones. Their structures were established based on extensive spectroscopic data analyses, including IR, UV, HRESIMS, 1D NMR and 2D NMR. Absolute configurations were determined by ECD calculation method and chemical degradation. In addition, all compounds were evaluated for their antiviral activity against influenza A (H1N1) virus and several were further evaluated against respiratory syncytial virus (RSV) in vitro. Among them, two previously known compounds showed significant activities against RSV with EC50 values of 3.43 and 6.72 ?M. PMID:24833035

Li, Chang; Dai, Yi; Zhang, Shu-Xiang; Duan, Ying-Hui; Liu, Ming-Li; Chen, Liu-Yuan; Yao, Xin-Sheng

2014-08-01

42

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

NASA Astrophysics Data System (ADS)

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.

K?en, Vladimír

43

Cardiac glycosides from erysimum cheiranthoides.  

PubMed

Two new cardiac glycosides were isolated from the seeds of Erysimum cheiranthoides. Their structures were characterized as strophanthidin glycosides of 3-O-alpha-L-rhamnopyranosyl-(1-->4)-3-O-acetyl-beta-D-digitoxopyranosyl and 3-O-beta-D-glucpyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-3-O-acetyl-beta-D-digitoxopyranosyl. PMID:11711105

Lei, Zhen Huan; Jin, Zhe Xion; Ma, Ying Li; Tai, Bao Shan; Kong, Qi; Yahara, Shoji; Nohara, Toshihiro

1998-11-20

44

Glycosyl fluorides in glycosidations.  

PubMed

This short review deals with the recent progress in chemical O-glycosidation and C-glycosylation methods using glycosyl fluorides as glycosyl donors. Pyranosyl and furanosyl fluorides were effectively activated by fluorophilic reagents such as SnCl2-AgClO4, SnCl2-TrClO4, SnCl2-AgOTf, TMSOTf, SiF4, BF3 x Et2O, TiF4, SnF4, Cp2MCl2-AgClO4 (M = Zr or Hf), Cp2ZrCl2-AgBF4, Cp2HfCl2-AgOTf, Bu2Sn(ClO4)2, Me2GaCl, Tf2O, LiClO4, Yb(OTf)3, La(ClO4)3 x nH2O, La(ClO4)3 x nH2O-Sn(OTf)2, Yb-Amberlyst 15, SO4/ZrO2, Nafion-H, montmorillonite K-10, and TrB(C6F5)4 to react with alcohols to give the corresponding O-glycosides in high yields. Furthermore, several types of C-glycosyl compounds, such as aryl, allyl and alkyl C-glycosyl derivatives, were also obtained by the glycosylation using glycosyl fluorides and the corresponding nucleophile with or without a Lewis acid. PMID:10968674

Toshima, K

2000-07-10

45

Synthesis and Photochromic Properties of Configurationally Varied Azobenzene Glycosides  

PubMed Central

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.

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

2014-01-01

46

Naturally occurring methyl salicylate glycosides.  

PubMed

As an important part of non steroids anti-inflammation drug (NSAIDs), salicylate has developed from natural substance salicylic acid to natrium salicylicum, to aspirin. Now, methyl salicylate glycoside, a new derivative of salicylic acid, is modified with a -COOH group integrated one methyl radical into formic ether, and a -OH linked with a monosaccharide, a disaccharide or a trisaccharide unit by glycosidic linkage. It has the similar pharmacological activities, anti-inflammatory, analgesic, antipyretic and antithrombotic as the previous salicylates' without resulting in serious side effects, particularly the gastrointestinal toxicity. Owing to the superiority of those significant bioactivities, methyl salicylate glycosides have became a hot research area in NSAIDs for several years. This paper compiles all 9 naturally occurring methyl salicylate glycosides, their distribution of the resource and pharmacological mechanism, which could contribute to the new drug discovery. PMID:24329991

Mao, Ping; Liu, Zizhen; Xie, Meng; Jiang, Rui; Liu, Weirui; Wang, Xiaohong; Meng, Shen; She, Gaimei

2014-01-01

47

Phenylpropanoid glycosides from Smilax glabra  

Microsoft Academic Search

Five phenylpropanoid esters of sucrose glycosides, trivially named smiglasides A–E, were isolated from the rhizomes of Smilax glabra. Their structures were elucidated on the basis of spectroscopic studies.

Ting Chen; Jian-Xin Li; Qiang Xu

2000-01-01

48

Flavanone glycosides from Alhagi pseudalhagi  

Microsoft Academic Search

Two new flavanone glycosides, alhagitin and alhagidin, have been isolated from the whole plant of Alhagi pseudalhagi and their structures established respectively as naringenin 5-methyl ether 4?-glucoside and hesperitin 7-galactosyl(1?2)[rhamnosyl(1?6)]glucoside by chemical and spectroscopic methods.

V. P Singh; Bineeta Yadav; V. B Pandey

1999-01-01

49

Flavanone glycosides from Alhagi pseudalhagi.  

PubMed

Two new flavanone glycosides, alhagitin and alhagidin, have been isolated from the whole plant of Alhagi pseudalhagi and their structures established respectively as naringenin 5-methyl ether 4'-glucoside and hesperitin 7-galactosyl(1-->2)[rhamnosyl(1-->6)]glucoside by chemical and spectroscopic methods. PMID:10389270

Singh, V P; Yadav, B; Pandey, V B

1999-06-01

50

Anticancer activity of cardiac glycosides  

PubMed Central

Retrospective clinical data indicate that cardiac glycosides (CGs), notably digoxin, prolong the survival of carcinoma patients treated with conventional chemotherapy. CGs are known to influence the immune response at multiple levels. In addition, recent results suggest that CGs trigger the immunogenic demise of cancer cells, an effect that most likely contributes to their clinical anticancer activity.

Kepp, Oliver; Menger, Laurie; Vacchelli, Erika; Adjemian, Sandy; Martins, Isabelle; Ma, Yuting; Sukkurwala, Abdul Qader; Michaud, Mickael; Galluzzi, Lorenzo; Zitvogel, Laurence; Kroemer, Guido

2012-01-01

51

Myricetin glycosides from Licania densiflora.  

PubMed

Dried leaves of Licania densiflora yielded five myricetin glycosides: myricetin 3'-methylether-3-O-glucoside (1), myricetin 3'-methylether-3-O-galactoside (2), myricetin 4'-methylether-3-O-rhamnoside (3), myricetin 3',5'-dimethylether-3-O-glucoside (4), and myricetin 3',5'-dimethylether-3-O-rhamnoside (5). Their structures were elucidated by spectroscopic methods including mono- and bi-dimensional NMR techniques. PMID:11223232

Braca, A; Bilia, A R; Mendez, J; Morelli, I

2001-02-01

52

Cardiac glycosides from Erysimum cheiranthoides.  

PubMed

Two new cardiac glycosides called cheiranthosides VI (2) and VII (3) were isolated together with a known one, glucoerysimoside (1) from the seeds of Erysimum cheiranthoides. Based on spectroscopic data, the structures of 2 and 3 were characterized as periplogenin 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-fucopyranoside and periplogenin 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-antiaropyranoside, respectively. PMID:10705523

Lei, Z H; Yahara, S; Nohara, T; Tai, B S; Xiong, J Z; Ma, Y L

2000-02-01

53

Cytotoxic phenylethanol glycosides from Psidium guaijava seeds  

Microsoft Academic Search

Phytochemical investigations of the acetone extract of Psidium guaijava seeds has led to the isolation of five known flavonoid glycosides, two phenolic glycosides and two new phenylethanoid glycosides which have been identified as 1-O-3,4-dimethoxy-phenylethyl-4-O-3,4-dimethoxy cinnamoyl-6-O-cinnamoyl-?-d-glucopyranose and 1-O-3,4-dimethoxyphenylethyl-4-O-3,4-dimethoxy cinnamoyl-?-d-glucopyranose, on the basis of chemical, physical and spectroscopic methods of analysis.

Josline Y. Salib; Helana N. Michael

2004-01-01

54

[The antifungal action of polygalacic acid glycosides].  

PubMed

Triterpenoid glycosides obtained from Solidago virgaurea L. and Bellis perennis L. (Asteraceae) inhibit the growth of human-pathogenic yeasts (Candida and Cryptococcus species). First results are given of the investigations on the mode of action and the relationships between structure and activity of these compounds. The intensity of growth inhibition is influenced particularly by the carbohydrate chains of the glycosides. Monodesmosidic as well as bisdesmosidic glycosides of polygalacic acid exert fungicidic effects. PMID:2080212

Bader, G; Kulhanek, Y; Ziegler-Böhme, H

1990-07-01

55

Cardiac glycosides from Erysimum cheiranthoides.  

PubMed

Three new cardiac glycosides named cheiranthoside VIII (1), cheiranthoside IX (2) and cheiranthoside X (3) were isolated from the seeds of Erysimum cheiranthoides. Based on spectroscopic data, the structures of 1-3 were characterized as strophanthidin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-antiaropyranoside, cheiranthidin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-boiviopyranoside and cheiranthidin 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-digitoxopyranoside, respectively. The aglycone moiety possessing a carboxyl group at C-10 of 2 and 3 was regarded to be determined for the first time. PMID:12045350

Lei, Zhen-Huan; Nakayama, Hitoshi; Kuniyasu, Akihiko; Tai, Bao-Shan; Nohara, Toshihiro

2002-06-01

56

A case of nondigitalis cardiac glycoside toxicity.  

PubMed

A case is presented of cardiac glycoside poisoning in a 1-year-old patient from the plant Nerium oleander (common oleander). The patient had bradycardia, vomiting, altered level of consciousness, and no history of ingestion. Antibody-based digoxin assays may cross-react with other cardiac glycosides nonquantitatively. Chromatographic techniques can be used in the specific diagnosis. PMID:9421116

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

1997-12-01

57

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

PubMed

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

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

2008-10-01

58

New kaurene diterpenoid glycosides from fenugreek seeds.  

PubMed

Two new kaurene diterpenoid glycosides, named Graecumoside A (1) and B (2), were isolated from fenugreek seeds, along with three known flavonoid-C-glycosides, isoorientin (3), isovitexin (4) and vitexin (5). By combined analyses of 1D- and 2D-NMR, and MS spectroscopy, the structures of two new compounds were elucidated as 3-O-?- D-glucopyranosyl kaur-5, 16-dien-3?, 6, 13?-trihydroxy-7-oxo-18-oic acid methyl ester and 3-O-?-neohesperidosyl kaur-5, 16-dien-3?, 6, 13?-trihydroxy-7-oxo-18-oic acid methyl ester, respectively. The kaurene diterpenoid glycosides were first isolated and identified from fenugreek seeds. PMID:22950814

Pang, Xu; Kang, Li-Ping; Yu, He-Shui; Zhao, Yang; Xiong, Cheng-Qi; Zhang, Jie; Ma, Bai-Ping

2013-01-01

59

A new furostanol glycoside from Tribulus terrestris.  

PubMed

Besides two known glycosides, a new furostanol glycoside was isolated from the Fruits of Tribulus terrestris L. The structure of the new furostanol glycoside was established as 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furostane-20(22)-en-12-one-3beta, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (1) on the basis of 1D and 2D-NMR techniques, including COSY, HMBC, and HMQC correlations. PMID:20335931

Xu, Yajuan; Liu, Yonghong; Xu, Tunhai; Xie, Shengxu; Si, Yunshan; Liu, Yue; Zhou, Haiou; Liu, Tonghua; Xu, Dongming

2010-02-01

60

Glycerol Glycoside Esters of Fatty Acids.  

National Technical Information Service (NTIS)

The patent application relates to compositions of matter containing esters of glycosides and 6 to 24 carbon atom fatty acids, which compositions are useful as surface-active agents. More particularly, this invention relates to compositions of matter obtai...

R. O. Feuge J. L. White M. L. Brown

1974-01-01

61

Four new cycloartane glycosides from Aquilegia vulgaris.  

PubMed

Four new cycloartane glycosides, named aquilegiosides G-J, were isolated from the dried aerial parts of Aquilegia vulgaris. Their structures were determined by spectroscopic analysis and chemical evidence. PMID:12913235

Nishida, Makiko; Yoshimitsu, Hitoshi; Okawa, Masafumi; Nohara, Toshihiro

2003-08-01

62

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

PubMed

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

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

2012-01-01

63

Phytosterol glycosides reduce cholesterol absorption in humans  

PubMed Central

Dietary phytosterols inhibit intestinal cholesterol absorption and regulate whole body cholesterol excretion and balance. However, they are biochemically heterogeneous and a portion is glycosylated in some foods with unknown effects on biological activity. We tested the hypothesis that phytosterol glycosides reduce cholesterol absorption in humans. Phytosterol glycosides were extracted and purified from soy lecithin in a novel two-step process. Cholesterol absorption was measured in a series of three single-meal tests given at intervals of 2 wk to each of 11 healthy subjects. In a randomized crossover design, participants received ?300 mg of added phytosterols in the form of phytosterol glycosides or phytosterol esters, or placebo in a test breakfast also containing 30 mg cholesterol-d7. Cholesterol absorption was estimated by mass spectrometry of plasma cholesterol-d7 enrichment 4–5 days after each test. Compared with the placebo test, phytosterol glycosides reduced cholesterol absorption by 37.6 ± 4.8% (P < 0.0001) and phytosterol esters 30.6 ± 3.9% (P = 0.0001). These results suggest that natural phytosterol glycosides purified from lecithin are bioactive in humans and should be included in methods of phytosterol analysis and tables of food phytosterol content.

Lin, Xiaobo; Ma, Lina; Racette, Susan B.; Anderson Spearie, Catherine L.; Ostlund, Richard E.

2009-01-01

64

Diterpene glycosides from Stevia phlebophylla A. Gray.  

PubMed

The rare Mexican species Stevia phlebophylla A. Gray was long considered to be the only known Stevia species, beside the well-known S. rebaudiana, containing the highly sweet diterpenoid steviol glycosides. We report a re-evaluation of this claim after phytochemically screening leaves obtained from two herbarium specimens of S. phlebophylla for the presence of steviol glycosides. Despite extensive MS analyses, no steviol glycosides could be unambiguously verified. Instead, the main chromatographic peak eluting at retention times similar to those of steviol glycosides was identified as a new compound, namely 16?-hydroxy-17-acetoxy-ent-kauran-19-oic acid-(6-O-?-D-xylopyranosyl-?-D-glucopyranosyl) ester (1) on the basis of extensive NMR and MS data as well as the characterization of its acid hydrolysate. Seven more compounds were detected by ESIMS which are possibly structurally related to 1. It can therefore be concluded that S. phlebophylla is unlikely to contain significant amounts of steviol glycosides, if any. PMID:23831634

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

2013-09-20

65

Steviol glycosides: chemical diversity, metabolism, and function.  

PubMed

Steviol glycosides are a group of highly sweet diterpene glycosides discovered in only a few plant species, most notably the Paraguayan shrub Stevia rebaudiana. During the past few decades, the nutritional and pharmacological benefits of these secondary metabolites have become increasingly apparent. While these properties are now widely recognized, many aspects related to their in vivo biochemistry and metabolism and their relationship to the overall plant physiology of S. rebaudiana are not yet understood. Furthermore, the large size of the steviol glycoside pool commonly found within S. rebaudiana leaves implies a significant metabolic investment and poses questions regarding the benefits S. rebaudiana might gain from their accumulation. The current review intends to thoroughly discuss the available knowledge on these issues. PMID:23713723

Ceunen, Stijn; Geuns, Jan M C

2013-06-28

66

Flower color diversity revealed by differential expression of flavonoid biosynthetic genes and flavonoid accumulation in herbaceous peony (Paeonia lactiflora Pall.).  

PubMed

Herbaceous peony (Paeonia lactiflora Pall.) is an important ornamental plant which contains different flower colors. In this paper, eight genes encoding phenylalanine ammonialyase (PAL), chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), flavonoid 3'-hydroxylase (F3'H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), UDP-glucose: flavonoid 3-o-glucosyltransferase (UF3GT) were isolated. Moreover, the expression patterns of these eight genes and UF5GT in the flowers were investigated in three cultivars, that is, 'Hongyanzhenghui', 'Yulouhongxing' and 'Huangjinlun' with purplish-red, white and yellow flower respectively. Furthermore, flavonoid accumulation in the flowers was also analyzed. The results showed that in different organs, most of genes expressed higher in flowers than in other organs. During the development of flowers, all genes could be divided into four groups. The first group (PlPAL) was highly expressed in S1 and S4. The second group (PlCHS and PlCHI) was at a high expression level throughout the whole developmental stages. The third group (PlF3H, PlF3'H, PlDFR, PlANS and PlUF5GT) gradually decreased with the development of flowers. The fourth group (PlUF3GT) gradually increased during the flower development. In addition, anthoxanthins and anthocyanins were detected in 'Hongyanzhenghui' and 'Yulouhongxing', chalcones and anthoxanthins were found in 'Huangjinlun'. When different color flowers were concerned, low expression level of PlCHI induced most of the substrate accumulation in the form of chalcones and displaying yellow, changing a small part of substrates to anthoxanthins, and there was no anthocyanin synthesis in 'Huangjinlun' because of low expression level of DFR. In 'Yulouhongxing', massive expressions of upstream genes and low expression of DFR caused synthesis of a great deal of anthoxanthins and a small amount of colorless anthocyanins. In 'Hongyanzhenghui', a large number of colored anthocyanins were changed from anthoxanthins because of PlDFR, PlANS and PlUF3GT high expressions. These results would provide us a theoretical basis to understand the formation of P. lactiflora flower colors. PMID:23054003

Zhao, Daqiu; Tao, Jun; Han, Chenxia; Ge, Jintao

2012-12-01

67

Acylated flavonoid glycosides from Bassia muricata  

Microsoft Academic Search

From the arial parts of Bassia muricata, two acylated flavonoid glycosides quercetin-3-O-(6?-caffeoyl)-sophoroside and quercetin-3-O-(6?-feruloyl)-sophoroside have been isolated together with two known flavonoid glycosides quercetin-3-O-sophoroside and quercetin-3,7-O-?-diglucopyranoside, as well as four known triterpenoidal saponins, oleanolic acid-3-O-?-glucopyranoside, chikusetsusaponin IVa, chikusetsusaponin IVa methyl ester and oleanolic acid-3,28-?-diglucopyranoside. The structures of the isolated compounds were verified by means of MS and NMR spectral analyses.

Mohamed S. Kamel; Khaled M. Mohamed; Hashim A. Hassanean; Kazuhiro Ohtani; Ryoji Kasai; Kazuo Yamasaki

2001-01-01

68

Acylated flavonoid glycosides from Bassia muricata.  

PubMed

From the arial parts of Bassia muricata, two acylated flavonoid glycosides quercetin-3-O-(6"-caffeoyl)-sophoroside and quercetin-3-O-(6"-feruloyl)-sophoroside have been isolated together with two known flavonoid glycosides quercetin-3-O-sophoroside and quercetin-3,7-O-beta-diglucopyranoside, as well as four known triterpenoidal saponins, oleanolic acid-3-O-beta-glucopyranoside, chikusetsusaponin IVa, chikusetsusaponin IVa methyl ester and oleanolic acid-3,28-beta-diglucopyranoside. The structures of the isolated compounds were verified by means of MS and NMR spectral analyses. PMID:11454355

Kamel, M S; Mohamed, K M; Hassanean, H A; Ohtani, K; Kasai, R; Yamasaki, K

2001-08-01

69

New minor glycoside components from saffron.  

PubMed

Phytochemical investigation of the stigmas of Crocus sativus resulted in the isolation of eight glycosides (1-8) including a new safranal glycoside (2) and a new carotenoid pigment (6). The structures of the new compounds were identified as (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde 4-O-[?-D-glucopyranosyl(1 ? 3)-?-D-glucopyranoside] (2) and trans-crocetin-1-al 1-O-?-gentiobiosyl ester (6) on the basis of extensive chemical and spectroscopic evidence. PMID:23179314

Tung, Nguyen Huu; Shoyama, Yukihiro

2013-07-01

70

Bioactive phenylpropanoid glycosides from Tabebuia avellanedae.  

PubMed

Three novel phenylpropanoid glycosides 2, 5, 6 were isolated from water extract of Tabebuia avellanedae, together with three known phenylpropanoid glycosides 1, 3, 4. All compounds were identified on the basis of spectroscopic analysis and chemical methods and, for known compounds, by comparison with published data. All isolated compounds showed strong antioxidant activity in the DPPH assay, and compound 5 give the highest antioxidant activity among all compounds, with an IC?? of 0.12 µM. All compounds exhibited moderate inhibitory effect on cytochrome CYP3A4 enzyme. PMID:23797703

Suo, Maorong; Ohta, Tomihisa; Takano, Fumihide; Jin, Shouwen

2013-01-01

71

Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana.  

PubMed

Two elemanolide sesquiterpenes and two eudesmane-type sesquiterpene glycosides named hierapolitanins A-D, were isolated, together with five known compounds, two flavones; hispidulin and jaceosidin, a flavon-C-glycoside, shaftoside, a flavonol glycoside, kaempferol-3-O-rutinoside and a neolignan, dehydrodiconiferyl alcohol from the aerial parts of Centaurea hierapolitana Boiss. (Asteraceae). Structure elucidations were based on spectroscopic evidence. PMID:17126864

Karamenderes, Canan; Bedir, Erdal; Pawar, Rahul; Baykan, Sura; Khan, Ikhlas A

2007-03-01

72

Two new glycosidic acids, quamoclinic acids G and H, of the resin glycosides (Convolvulin) from the seeds of Quamoclit pennata.  

PubMed

Two new glycosidic acids, quamoclinic acids G and H, were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction from the seeds of Quamoclit pennata BOJER. Both compounds are the first examples of bisdesmosides of glycosidic acid having the sugar linkages at C-3 of 3,11-dihydroxytetradecanoic acid (ipurolic acid) as well as at its C-11. PMID:20823606

Ono, Masateru; Imao, Masae; Miyahara, Kazumoto

2010-09-01

73

Identification and characterization of component organic and glycosidic acids of crude resin glycoside fraction from Calystegia soldanella.  

PubMed

Alkaline hydrolysis of the crude resin glycoside fraction of the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae) gave four new glycosidic acids, named calysolic acids A, B, C, and D, along with one known glycosidic acid, soldanellic acid B, and three organic acids, 2S-methylbutyric, tiglic, and 2S,3S-nilic acids. The structures of the new glycosidic acids were characterized on the basis of spectroscopic data and chemical evidence. PMID:21881263

Takigawa, Ayako; Setoguchi, Hiroaki; Okawa, Masafumi; Kinjo, Junei; Miyashita, Hiroyuki; Yokomizo, Kazumi; Yoshimitsu, Hitoshi; Nohara, Toshihiro; Ono, Masateru

2011-01-01

74

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)

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. 300°C 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.

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

2011-06-01

75

Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl.  

PubMed

Two new maltol glycosides, maltol 6'-O-beta-D-apiofuranosyl-beta-D-glucopyranoside and maltol 6'-O-(5-O-p-coumaroyl)-beta-D-apiofuranosyl-beta-D-glucopyranoside, were isolated from Elsholtzia rugulosa Hemsl. along with 11 known compounds including prunasin and amygdalin. The structures were determined on the basis of spectroscopic and chemical evidence. This is the second example of isolation of cyanogenic glycosides from Lamiaceous plants. PMID:18404347

Li, Haizhou; Nakashima, Tatsuya; Tanaka, Takashi; Zhang, Ying-Jun; Yang, Chong-Ren; Kouno, Isao

2008-01-01

76

Pregnane glycosides from fruits of Balanites aegyptiaca  

Microsoft Academic Search

From the mesocarp of Balanites aegyptiaca fruits, two pregnane glycosides were isolated. One is new and identified as pregn-5-ene-3?,16?,20(R)-triol 3-O-(2,6-di-O-?-l-rhamnopyranosyl)-?-d-glucopyranoside (balagyptin), while the other is known and assigned as pregn-5-ene-3?,16?,20(R)-triol 3-O-?-d-glucopyranoside.

M. S. Kamel; A. Koskinen

1995-01-01

77

A new lignan glycoside from Peperomia duclouxii.  

PubMed

A new lignan glycoside was isolated from the n-BuOH extract of Peperomia duclouxii C. DC., and its structure was elucidated to be 2-(4''-hydroxy-3'', 5''-dimethoxybenzyl)-3-(5'-methoxy-3', 4'-methylenedioxybenzyl)butyrolactone-4''-O-beta-D-glucopyranoside (1) by spectral methods. PMID:19023812

Zhu, Yan Hui; Li, Na; Wang, Ming-Wei

2008-01-01

78

A new chromene glycoside from Tithonia diversifolia  

Microsoft Academic Search

A new chromene glycoside, 6-acetyl-2,2-dimethylchromene-8-O-?-D-glucoside, together with four known compounds were isolated from the aerial parts of Tithonia diversifolia. Their structures\\u000a were established by 1H, 13C NMR, and HMQC together with the other physical and chemical investigations.

Hong-li Zhai; Gui-jun Zhao; Gen-jin Yang; He Sun; Bo Yi; Lian-na Sun; Wan-sheng Chen; Shui-qing Zheng

2010-01-01

79

Chlorination Diversifies Cimicifuga racemosa Triterpene Glycosides  

PubMed Central

Extracts from roots and rhizomes of black cohosh (Cimicifuga racemosa) are widely used as dietary supplements to alleviate menopausal symptoms. State-of-the-art QC 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 ans initially thought to be cimicifugoside (2). Detailed HR-LC-MS and 1/2D NMR analysis of 1 and 2 unambiguously revealed that 1 is its chlorine-containing derivative of 2, namely 25-chlorodeoxycimigenol-3-O-?-D-xyloside. Accordingly, HPLC profiles of black cohosh preparations require revision of the assignments of the chlorinated (1) and non-chlorinated (2) pair. Besides explaining the substantial shift in polarity (?tR[RP-18] ca 20 min), 25-deoxychlorination opens a new pathway of structural diversification in triterpene glycosides 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 pro drug”) of the relatively polar triterpene glycosides into significantly less polar chlorinated derivatives with altered pharmacological properties.

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.

2008-01-01

80

?-Chymotrypsin inhibiting benzylated glycosides from Symplocos racemosa  

Microsoft Academic Search

Three new benzylated glycosides, locoracemosides A, B and C (1–3) were isolated from the bark of the stem of Symplocos racemosa Roxb. Their structures were determined by spectroscopic and chemical evidences. They displayed in vitro inhibitory activity against ?-chymotrypsin.

Muhammad A. Rashid; Viqar U. Ahmad; Muhammad A. Abbasi; Zulfiqar Ali; Nasir Rasool; Muhammad Zubair; Muhammad A. Lodhi; Muhammad I. Choudhary; Ikhlas A. Khan

2008-01-01

81

A new withanolide glycoside from physalis peruviana  

PubMed

A new withanolide glycoside, 17beta-hydroxy-14, 20-epoxy-1-oxo-[22R]-3beta-[O-beta-D-glucopyranosyl]-witha-5, 24-dienolide (1), has been isolated from the whole plant of Physalis peruviana. Its identity was determined using a combination of spectroscopic data including 2D NMR techniques and chemical transformations. PMID:10096867

Ahmad; Malik; Afza; Yasmin

1999-03-01

82

Nivyaside — A new glycoside from Leucanthemum vulgare  

Microsoft Academic Search

From the ligulate flowers ofLeucanthemum vulgare Lam. growing on the territory of the Georgian SSR a new glycoside has been isolated which has been called nivyaside and has\\u000a the structure 8-(1-?-D-glucopyranosyl-5-deoxyquercit-5-yl)-4?,5,7-trihydroxyflavone.

T. G. Sagareishvili; M. D. Alaniya; V. S. Kikoladze; É. P. Kemertelidze

1982-01-01

83

Two New Caffeyol Glycosides from Forsythia suspensa  

Microsoft Academic Search

Two new caffeoyl glycosides of phenethyl alcohol, suspensaside A (1) and suspensaside B (2), were isolated from the fruits of Forsythia suspensa. Also obtained in this investigation were two known compounds forsythiaside (3) and suspensaside (4). The structures of compounds 1 and 2 were established by 1D and 2D NMR techniques and chemical methods.

Dong-Sheng Ming; De-Quan Yu; Shi-Shan Yu

1999-01-01

84

New triterpene glycosides from Ziziphi Spinosae Semen.  

PubMed

Four new dammarane-type triterpene glycosides, named jujubosides I-IV (1-4), were isolated from Ziziphi Spinosae Semen, along with seven known saponins (5-11). The structures of new compounds were established on the basis of extensive spectroscopic analysis. All compounds were evaluated for the effects on neonatal rat cardiomyocyte injury induced by hydrogen peroxide in vitro. PMID:23912064

Wang, Yu; Ding, Bo; Luo, Dan; Chen, Liu-Yuan; Hou, Yun-Long; Dai, Yi; Yao, Xin-Sheng

2013-10-01

85

A new aromatic glycoside from Glehnia littoralis.  

PubMed

A new aromatic glycoside (1) was isolated from the roots of Glehnia littoralis Fr. Schmidtex Miq. Its structure was elucidated as vanillic acid 1-O-[?-D-apiofuranosyl-(1 ? 6)-?-D-glucopyranoside] ester mainly by analysing the NMR and MS spectral data. In the in vitro assays, compound 1 displayed some TNF-? secretion inhibitory activity. PMID:24547738

Feng, Zi-Jin; Zhang, Xiao-Hong; Zhang, Jian-Peng; Shang, Xiao-Hui; Gao, Yun; Lu, Xiao-Ling; Liu, Xiao-Yu; Jiao, Bing-Hua

2014-01-01

86

Two methoxylated flavone glycosides from Bidens pilosa  

Microsoft Academic Search

Two methoxylated flavone glycosides were identified as the novel quercetin 3,3?-dimethyl ether 7-O-?-d-rhamnopyranosyl-(1 ? 6)-?-d-glucopyranoside and the known quercetin 3,3?-dimethyl ether 7-O-?-d-glucopyranoside from the roots of Bidens pilosa.

M. G. L. Brandăo; C. G. C. Nery; M. A. S. Mamăo; A. U. Krettli

1998-01-01

87

Enzymatic Processing of Bioactive Glycosides from Natural Sources  

NASA Astrophysics Data System (ADS)

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.

Weignerová, Lenka; K?en, Vladimír

88

Determination of triterpene glycosides in sea cucumber (Stichopus japonicus) and its related products by high-performance liquid chromatography.  

PubMed

A creative and sensitive method has been developed for the determination of triterpene glycosides concentrations in sea cucumber ( Stichopus japonicus) and related products by using d-quinovose (6-deoxyglucose) as the measurement standard by reverse-phase high-performance liquid chromatography (HPLC) and variable-wavelength detection. d-quinovose, which is a unique monosaccharide in holostane triterpene glycosides, was liberated by acid hydrolysis and precolumn derivatized by 1-phenyl-3-methyl-5-pyrazolone (PMP). PMP-quinovose was analyzed by HPLC with 22% acetonitrile in 0.05 M KH2PO4 aquatic solution (pH 5.2) as mobile phase. The calibration curves of d-quinovose were linear within the range of 6.56-164 mg/L (r(2) > 0.995). The contents of triterpene glycosides in various S. japonicus products were determined after appropriate pretreatment methods. The concentration of triterpene glycosides was calculated by the formula C = C(qui) x alpha (alpha = 8.5). The result showed that this method was a simple, rapid, and stable method for the determination of triterpene glycosides in S. japonicus products. PMID:18557622

Dong, Ping; Xue, Chang-Hu; Yu, Lin-Fang; Xu, Jie; Chen, Shi-Guo

2008-07-01

89

Sesquiterpenoid glycosides from glandular trichomes of the wild tomato relative Solanum habrochaites.  

PubMed

Profiles of terpenoid glycoside metabolites in glandular trichomes of Solanum habrochaites LA1777 leaves were generated using ultrahigh performance liquid chromatography/time-of-flight mass spectrometry with multiplexing of non-selective collision-induced dissociation (CID). Profiling data suggested a diverse group of 52 sesquiterpenoid glycosides, and fragment ions observed in both non-selective CID mass spectra and true tandem mass spectrometry (MS/MS) product ion spectra documented variation in extent of glycosylation and the presence of malonate or acetate esters. Up to 10 isomers were detected for some metabolites. Malonate and acetate esters of three sesquiterpene diol glucosides and one unmodified diglucoside were purified using reversed phase semipreparative HPLC and analyzed and identified using 1D and 2D NMR and mass spectrometry. All four of the isolated products were glucosides of campheranane-2,12-diol. PMID:24333030

Ekanayaka, E A Prabodha; Li, Chao; Jones, A Daniel

2014-02-01

90

Five phenolic glycosides from Alangium chinense.  

PubMed

From the dried leaves of Alangium chinense, five novel phenolic glycosides, 6'-O-galloylsalicin (1); 4',6'-di-O-galloylsalicin (2); 4',6'-O-(S)-hexahydroxydiphenoylsalicin (3); 4', 6'-O-(R)-hexahydroxydiphenoylsalicin (4); and pyrocatechol 1-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside (5) were isolated. The structures of these new compounds were determined by spectroscopic methods. PMID:10650086

Itoh, A; Tanahashi, T; Ikejima (née Sato), S; Inoue, M; Nagakura, N; Inoue, K; Kuwajima, H; Wu, H X

2000-01-01

91

Pregnane glycosides from fruits of Balanites aegyptiaca.  

PubMed

From the mesocarp of Balanites aegyptiaca fruits, two pregnane glycosides were isolated. One is new and identified as pregn-5-ene-3 beta,16 beta,20(R)-triol 3-O-(2,6-di-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside (balagyptin), while the other is known and assigned as pregn-5-ene-3 beta,16 beta,20(R)-triol 3-O-beta-D-glucopyranoside. PMID:8590640

Kamel, M S; Koskinen, A

1995-12-01

92

New xanthone glycosides from Comastoma pedunculatum.  

PubMed

Five new xanthone glycosides, comastomasides A-E (1-5), were isolated from aqueous ethanol extracts of the aerial portions of Comastoma pedunculatum. The structures of these compounds were elucidated by spectroscopic analysis methods. Compounds 1-5 were evaluated for their hepatoprotective activity and cytotoxicity against four human cancer cell lines by in vitro assays. Among them, compounds 3 and 5 exhibited potent hepatoprotective activity. However, none of the compounds displayed cytotoxic activity. PMID:22814820

Qiao, Yongqi; Yuan, Yi; Cui, Baosong; Zhang, Ying; Chen, Hui; Li, Shuai; Li, Yan

2012-09-01

93

Laccase-mediated oxidation of natural glycosides  

Microsoft Academic Search

Regioselective oxidations of the primary OH's of natural glycosides (thiocolchicoside, colchicoside, amygdalin, asiaticoside, ginsenoside RE) have been performed on a preparative scale by exploiting the laccase–2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) methodology. The influence of water-miscible organic cosolvents on the stability and activity of a laccase from Trametes pubescens has been investigated. The enzyme has been covalently linked to Eupergit C250L and its performances

Lara Baratto; Andrea Candido; Mattia Marzorati; Francesca Sagui; Sergio Riva; Bruno Danieli

2006-01-01

94

A phenylpropanoid glycoside from Ballota nigra.  

PubMed

A new phenylpropanoid glycoside, ballotetroside, has been isolated from the aerial parts of Ballota nigra. On the basis of chemical and spectral data, its structure has been established as (3,4-dihydroxyphenyl)-2-ethyl[alpha-L-arabinopyranosyl-(1-->2)-alp ha- L-rhamnopyranosyl-(1-->3)]-beta-D-apiofuranosyl-(1-->6)-4-O- caffeoyl-beta-D-glucopyranoside. PMID:9041717

Seidel, V; Bailleul, F; Libot, F; Tillequin, F

1997-02-01

95

New jujubogenin glycosides from Colubrina asiatica.  

PubMed

Three new jujubogenin glycosides, namely, 3' '-O-acetylcolubrin (1); 3' ',2' "-O-diacetylcolubrin (2), and 3' '-O-acetyl-6' '-O-trans-crotonylcolubrin (3), were isolated from the leaves of Colubrina asiatica, in addition to the known colubrin, rutin, and kaempferol 3-O-rutinoside. Compounds 1-3 were isolated and purified via a combination of chromatographic procedures, and determined structurally using spectroscopic methods. PMID:11087616

Lee, S S; Chen, W C; Chen, C H

2000-11-01

96

?-cyclodextrin assistant flavonoid glycosides enzymatic hydrolysis  

PubMed Central

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 60°C and 28 times from 7.78 ?g/ml to 221.46 ?g/ml at 50°C, 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.

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

2013-01-01

97

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

Microsoft Academic Search

Cyanogenic glycosides are ancient biomolecules found in more than 2,650 higher plant species as well as in a few arthropod species. Cyanogenic glycosides are amino acid-derived ?-glycosides of ?-hydroxynitriles. In analogy to cyanogenic plants, cyanogenic arthropods may use cyanogenic glycosides as defence compounds. Many of these arthropod species have been shown to de novo synthesize cyanogenic glycosides by biochemical pathways

Sřren Bak; Susanne Michelle Paquette; Marc Morant; Anne Vinther Morant; Shigeki Saito; Nanna Bjarnholt; Mika Zagrobelny; Kirsten Jřrgensen; Sarah Osmani; Henrik Toft Simonsen; Raquel Sanchez Pérez; Torbjřrn Bordier van Heeswijck; Bodil Jřrgensen; Birger Lindberg Mřller

2006-01-01

98

Oleandrin: A cardiac glycosides with potent cytotoxicity.  

PubMed

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

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

2013-07-01

99

Alkyl and phenolic glycosides from Saussurea stella.  

PubMed

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

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

2013-04-01

100

New oxypregnane glycosides from appetite suppressant herbal supplement Hoodia gordonii  

Microsoft Academic Search

Hoodigosides A–K (1–11), eleven new oxypregnane glycosides and a previously reported oxypregnane glycoside P57AS3 were isolated from the aerial parts of Hoodia gordonii. The structures of these 12-O-?-tigloyl isoramanone glycosides were determined on the basis of chemical evidence and extensive spectroscopic methods that include one-dimensional and two-dimensional NMR. Cytotoxicity and antioxidant activities of these compounds were tested in cell based

Rahul S. Pawar; Yatin J. Shukla; Shabana I. Khan; Bharathi Avula; Ikhlas A. Khan

2007-01-01

101

Phenolic glycosides from Symplocos racemosa: natural inhibitors of phosphodiesterase I  

Microsoft Academic Search

One new phenolic glycoside named benzoylsalireposide (1) along with one known phenolic glycoside named salireposide (2) have been isolated from Symplocos racemosa. Four other known compounds i.e. ?-amyrin (3), oleonolic acid (4), ?-sitosterol (5) and ?-sitosterol glycoside (6) were also isolated from this plant. The structure elucidation of the isolated compounds was based primarily on 1D- and 2D-NMR analysis, including

Viqar Uddin Ahmad; Muhammad Athar Abbasi; Hidayat Hussain; Muhammad Nadeem Akhtar; Umar Farooq; Naheed Fatima; M. Iqbal Choudhary

2003-01-01

102

Lignan and neolignan glycosides from the roots of Glehnia littoralis.  

PubMed

A new lignan glycoside [glehlinoside G (1)] and three new neolignan glycosides [glehlinosides H (2), I (3) and J (4)] were isolated from the roots of Glehnia littoralis. Their structures were elucidated on the basis of spectroscopic data. The above glehlinosides (1-4), together with the other lignan and neolignan glycosides (5-12) from this plant, were evaluated for their prolyl oligopeptidase inhibitory activities, and a caffeoyled lignan glycoside (glehlinoside F, 8) exhibited a noticeable activity (IC(50) = 14.5?µM). PMID:20560111

Xu, Yi; Gu, Xue; Yuan, Zhong

2010-10-01

103

Cardiac glycosides from Yellow Oleander (Thevetia peruviana) seeds.  

PubMed

Thevetia cardiac glycosides can lead to intoxication, thus they are important indicators for forensic and pharmacologic surveys. Six thevetia cardiac glycosides, including two with unknown structures, were isolated from the seeds of the Yellow Oleander (Thevetia peruviana (Pers.) K. Shum., Apocynaceae). LC-ESI?-MS(/MS) analysis under high-resolution conditions used as a qualitative survey of the primary glycosides did not lead to fragmentation of the aglycones. Acid hydrolysis of the polar and non-volatile thevetia glycosides under severe conditions yielded the aglycones of the thevetia glycosides and made them amenable to GC-MS analysis. Comparison of mass spectral fragmentation patterns of the aglycones, as well as high-resolution mass spectrometric and NMR data of four of the primary thevetia glycosides including the two unknowns, revealed the structures of the complete set of six thevetia glycosides. The identified compounds are termed thevetin C and acetylthevetin C and differ by an 18,20-oxido-20,22-dihydro functionality from thevetin B and acetylthevetin B, respectively. The absence of an unsaturated lactone ring renders the glycosides cardio-inactive. The procedures developed in this study and the sets of analytical data obtained will be useful for screening and structure assessment of other, particularly polar, cardiac glycosides. PMID:22196940

Kohls, Sarah; Scholz-Böttcher, Barbara M; Teske, Jörg; Zark, Patrick; Rullkötter, Jürgen

2012-03-01

104

Cyanohydrin glycosides of Passiflora: distribution pattern, a saturated cyclopentane derivative from P. guatemalensis, and formation of pseudocyanogenic alpha-hydroxyamides as isolation artefacts.  

PubMed

Nineteen species of Passiflora (Passifloraceae) were examined for the presence of cyanogenic glycosides. Passibiflorin, a bisglycoside containing the 6-deoxy-beta-D-gulopyranosyl residue, was isolated from P. apetala, P. biflora, P. cuneata, P. indecora, P. murucuja and P. perfoliata. In some cases this glycoside co-occurs with simple beta-D-glucopyranosides: tetraphyllin A, deidaclin, tetraphyllin B, volkenin, epivolkenin and taraktophyllin. P. citrina contains passicapsin, a rare glycoside with the 2,6-dideoxy-beta-D-xylo-hexopyranosyl moiety, while P. herbertiana contains tetraphyllin A, deidaclin, epivolkenin and taraktophyllin, P. discophora tetraphyllin B and volkenin, and P. x violacea tetraphyllin B sulfate. The remaining species were noncyanogenic. The glycosides were identified by 1H and 13C NMR spectroscopy following isolation by reversed-phase preparative HPLC. From P. guatemalensis, a new glucoside named passiguatemalin was isolated and identified as a 1-(beta-D-glucopyranosyloxy)-2,3-dihydroxycyclopentane-1-carbonitrile. An isomeric glycoside was prepared by catalytic hydrogenation of gynocardin. alpha-Hydroxyamides corresponding to the cyanogenic glycosides were isolated from several Passiflora species. These alpha-hydroxyamides, presumably formed during processing of the plant material, behave as cyanogenic compounds when treated with commercial Helix pomatia crude enzyme preparation. Thus, the enzyme preparation appears to contain an amide dehydratase, which converts alpha-hydroxyamides to cyanohydrins that liberate cyanide; this finding is of interest in connection with analysis of plant tissues and extracts using Helix pomatia enzymes. PMID:11853745

Jaroszewski, Jerzy W; Olafsdottir, Elin S; Wellendorph, Petrine; Christensen, Jette; Franzyk, Henrik; Somanadhan, Brinda; Budnik, Bogdan A; Jřrgensen, Lise Bolt; Clausen, Vicki

2002-03-01

105

A chlorinated monoterpene ketone, acylated beta-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae).  

PubMed

Mentha longifolia (Lamiaceae), an aromatic herb yielded a new halogenated chloro-derivative of menthone (longifone), two new derivatives of beta-sitosterol glycoside (longiside-A and -B) and a new flavanone-glycoside (longitin). The beta-sitosterol and flavanone glycosides were purified as their acetate derivatives. Structures of all the isolated constituents were elucidated with the aid of HMBC techniques. However, the structure of longifone was also determined through X-ray crystallography. PMID:11937172

Shaiq Ali, Muhammad; Saleem, Muhammad; Ahmad, Waqar; Parvez, Masood; Yamdagni, Raghav

2002-04-01

106

Synthesis of cyclopropyl glycosides and their use as novel glycosyl donors.  

PubMed

Methods for the synthesis of cyclopropyl glycosides and their use as glycosyl donors are described. Cyclopropyl glycosides containing different substituents were prepared by cyclopropanation of the corresponding vinyl glycosides, or by glycosidation of cyclopropyl alcohols that are synthesized by the Kulinkovich reaction. 1-Methyl- and 1-phenyl-substituted cyclopropyl glycosides undergo coupling to Fmoc-protected serine and threonine and to partially protected monosaccharides in the presence of TMS triflate to give glycosidated products. PMID:22475156

Scholl, Clark; Licisyn, Thomas; Cummings, Christopher; Hughes, Kevin; Johnson, David; Boyko, Walter; Giuliano, Robert

2012-07-15

107

Secondary-emission mass spectrometry of hederagenin glycosides and medicagenic acid glycosides  

Microsoft Academic Search

The secondary emission (SE) spectra of six glycosides of medicagenic acid (MA) and of hederagenin have been studied. The (M + H)+ ions were observed in the secondary ion spectra (LSIMS) of mono- and biosides of MA and also of a triand a tetraoside of hederagenin in a glycerol matrix. The (M + Na)+ ions were recorded in the spectra

Yu. M. Mil'grom; Ya. V. Rashkes; A. É. Timbekova

1992-01-01

108

Steroid saponins X. Glycosides of Allium narcissiflorum the structure of glycosides A and B  

Microsoft Academic Search

Summary  FromAllium narcissiflorum Wells have been isolated for the first time trillin and a glycoside B, which proved to be 3-O-[?-O-D-glucopyranosyl-(1 ? 3)-O-?-D-glucopyranosyl-(1 ? 6)-O-?-D-glucopyranosyl-(1 ?]-26-O-[?-D-glucopyranosyl-(1 ?]-25R-furost-5-ene-3?,22 ?, 26-triol.

V. V. Krokhmalyuk; P. K. Kintya

1976-01-01

109

New phenanthrene glycosides from Dioscorea opposita.  

PubMed

Two new phenanthrene glycosides, dioscopposide A and dioscopposide B (1 and 2), were isolated from the rhizomes of Dioscorea opposita. Their structures were determined primarily on the basis of 1D and 2D NMR techniques, MS studies, and chemical methods. All the isolates were evaluated for their inhibitory effects on the lipopolysaccharide-induced nitric oxide production using murine macrophage RAW 264.7 cells. The IC50 values of dioscopposide A and dioscopposide B were 5.8 and 7.2 ?M, respectively. PMID:24168215

Zheng, Ken Yu-Zhong; Zhang, Zhen-Xia; Zhou, Wenliang; Cao, Hui; Xiang, Fei-Jun

2014-01-01

110

Glycosidic constituents from in vitro Anoectochilus formosanus.  

PubMed

The glycosidic constituents of whole plants of Anoectochilus formosanus propagated by tissue culture were investigated. A new compound, 2-(beta-D-glucopyranosyloxymethyl)-5-hydroxymethylfuran, along with the known compounds, 3-(R)-3-beta-D-glucopyranosyloxybutanolide (kinsenoside), 3-(R)-3-beta-D-glucopyranosyloxy-4-hydroxybutanoic acid, 1-O-isopropyl-beta-D-glucopyranoside, (R)-(+)-3,4-dihydroxy-butanoic acid y-lactone, 4-(beta-D-glucopyranosyloxy)benzyl alcohol, (6R,9S)-9-hydroxy-megastigma-4,7-dien-3-one-9-O-beta-glucopy ranoside, and corchoionoside C were isolated. PMID:11086921

Du, X M; Sun, N Y; Irino, N; Shoyama, Y

2000-11-01

111

Three new flavonoid glycosides from Urena lobata.  

PubMed

Three new flavonoid glycosides, kaempferol-3-O-?-D-apiofuranosyl(1 ? 2)-?-D-glucopyranosyl-7-O-?-L-rhamnopyranoside (1), kaempferol-4'-O-?-D-apiofuranosyl-3-O-?-D-glucopyranosyl-7-O-?-l-rhamnopyranoside (2), and 5,6,7,4'-tetrahydroxy-flavone-6-O-?-D-arabinopyranosyl-7-O-?-L-rhamnopyranoside (3), were isolated from the aerial parts of Urena lobata L., along with 10 known compounds (4-13). Their structures were determined based on spectroscopic methods including 1D and 2D NMR spectroscopy as well as HR-ESI-MS. PMID:21972805

Jia, Lu; A, You-Mei; Jing, Lin-Lin; Zhou, Sheng-An; Kong, De-Yun

2011-10-01

112

Reverse Transcriptase.  

National Technical Information Service (NTIS)

Contents: Purification and properties of reverse transcriptase; Biosynthesis of reverse transcriptase; Differentiation of cellular DNA polymerases from reverse transcriptase; Characterization of reverse transcriptase complexes in vivo and in vitro; Revers...

1982-01-01

113

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

PubMed Central

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

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

1995-01-01

114

Correlation between Platelet Gelsolin and Platelet Activation Level in Acute Myocardial Infarction Rats and Intervention Effect of Effective Components of Chuanxiong Rhizome and Red Peony Root  

PubMed Central

The biological role of platelet gelsolin in platelet activation of acute myocardial infarction is not defined. In order to provide a potential new antiplatelet target for Chinese medicine and to elucidate the contribution of Xiongshao capsule, the effective components of Chuanxiong rhizome and red peony root, in this study, we randomly allocated Sprague Dawley rats to left anterior descending coronary artery ligation or sham surgery and different drug prophylaxis as control. We found that gelsolin is highly expressed in platelet rich plasma and lowly expressed in platelet poor plasma, accompanied by the high platelet activation level in model rats; plasma actin filaments and mean fluorescence intensity (MFI) of platelet calcium ion increased and plasma vitamin D binding protein decreased in model rats. Xiongshao capsule could inhibit the gelsolin expression in platelet rich plasma and ischemic heart tissue simultaneously and reduce the level of plasma F-actin and MFI of platelet calcium ion. Our study concludes that platelet gelsolin is an important contributor to platelet activation, and platelet gelsolin inhibition may form a novel target for antiplatelet therapy. Xiongshao capsule may be a promising Chinese medicine drug for antiplatelet and aspirin-like cardioprotection effect.

Liu, Yue; Yin, Huijun; Jiang, Yuerong; Xue, Mei; Guo, Chunyu; Shi, Dazhuo; Chen, Keji

2013-01-01

115

Fully acetylated carbamate and hypotensive thiocarbamate glycosides from Moringa oleifera  

Microsoft Academic Search

Six new and three synthetically known glycosides have been isolated from the leaves of Moringa oleifera, employing a bioassay-directed isolation method on the ethanolic extract. Most of these compounds, bearing thiocarbamate, carbamate or nitrile groups, are fully acetylated glycosides, which are very rare in nature. Elucidation of the structures was made using chemical and spectroscopic methods, including 2D NMR techniques.

Shaheen Faizi; Bina Shaheen Siddiqui; Rubeena Saleem; Salimuzzaman Siddiqui; Khalid Aftab; Anwar-Ul-Hassan Gilani

1995-01-01

116

Resveratrol/phloroglucinol glycosides from the roots of Lysidice rhodostegia.  

PubMed

Two new phloroglucinol glycosides, lysidisides C (1) and D (2), together with two new resveratrol glycosides, lysidisides E (3) and F (4), were isolated from the n-BuOH extract of the roots of Lysidice rhodostegia. The structures were elucidated on the basis of spectroscopic and chemical evidence. The antioxidant activity of the isolates was also investigated PMID:17415877

Gao, Song; Liu, Jing; Fu, Guang-Miao; Hu, You-Cai; Yu, Shi-Shan; Fan, Li-Hua; Yu, De-Quan; Qu, Jing

2007-02-01

117

Evaluating the Cancer Therapeutic Potential of Cardiac Glycosides  

PubMed Central

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.

Calderon-Montano, Jose Manuel; Burgos-Moron, Estefania; Orta, Manuel Luis; Maldonado-Navas, Dolores; Garcia-Dominguez, Irene; Lopez-Lazaro, Miguel

2014-01-01

118

Antiproliferative cardiac glycosides from the latex of Antiaris toxicaria.  

PubMed

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

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

119

Enzymatic synthesis of epothilone A glycosides.  

PubMed

Epothilones are extremely cytotoxic chemotherapeutic agents with epoxide, thiazole, and ketone groups that share equipotent kinetic similarity with taxol. The in vitro glycosylation catalyzed by uridine diphosphate glucosyltransferase (YjiC) from Bacillus licheniformis generated six novel epothilone A glycoside analouges including epothilone A 7-O-?-D-glucoside, epothilone A 7-O-?-D-galactoside, epothilone A 3,7-O-?-D-digalactoside, epothilone A 7-O-?-D-2-deoxyglucoside, epothilone A 7-O-?-L-rhamnoside, and epothilone A 7-O-?-L-fucoside. Epothilone A 7-O-?-D-glucoside was structurally elucidated by ultra-high performance liquid chromatography-photo diode array (UPLC-PDA) conjugated with high resolution quantitative time-of-flight-electrospray ionization mass spectroscopy (HR-QTOF ESI-MS/MS) supported by one-and two-dimensional nuclear magnetic resonance studies whereas other epothilone A glycosides were characterized by UPLC-PDA and HR-QTOF ESI-MS/MS analyses. The time dependent conversion study of epothilone A to epothilone A 7-O-?-D-glucoside found to be maximum (~26%) between 3 h to 5 h incubation. PMID:24949266

Parajuli, Prakash; Pandey, Ramesh Prasad; Koirala, Niranjan; Yoon, Yeo Joon; Kim, Byung-Gee; Sohng, Jae Kyung

2014-01-01

120

Enzymatic synthesis of epothilone A glycosides  

PubMed Central

Epothilones are extremely cytotoxic chemotherapeutic agents with epoxide, thiazole, and ketone groups that share equipotent kinetic similarity with taxol. The in vitro glycosylation catalyzed by uridine diphosphate glucosyltransferase (YjiC) from Bacillus licheniformis generated six novel epothilone A glycoside analouges including epothilone A 7-O-?-D-glucoside, epothilone A 7-O-?-D-galactoside, epothilone A 3,7-O-?-D-digalactoside, epothilone A 7-O-?-D-2-deoxyglucoside, epothilone A 7-O-?-L-rhamnoside, and epothilone A 7-O-?-L-fucoside. Epothilone A 7-O-?-D-glucoside was structurally elucidated by ultra-high performance liquid chromatography-photo diode array (UPLC-PDA) conjugated with high resolution quantitative time-of-flight-electrospray ionization mass spectroscopy (HR-QTOF ESI-MS/MS) supported by one-and two-dimensional nuclear magnetic resonance studies whereas other epothilone A glycosides were characterized by UPLC-PDA and HR-QTOF ESI-MS/MS analyses. The time dependent conversion study of epothilone A to epothilone A 7-O-?-D-glucoside found to be maximum (~26%) between 3 h to 5 h incubation.

2014-01-01

121

An investigation of the kinetic and anti-angiogenic properties of plant glycoside inhibitors of thymidine phosphorylase  

Microsoft Academic Search

We investigated the potential of symplocomoside (1) and symponoside (2), glycosides isolated from the bark of Symplocos racemosa to inhibit thymidine phosphorylase (TP) activity and associated angiogenesis. Compound 1 was a reversible, noncompetitive inhibitor of deoxythymidine binding to TP (IC50 = 65.45 ± 5.08 ?M; Ki = 62.83 ± 2.10 ?M) and 2 was a reversible, uncompetitive inhibitor (IC50 = 94.17 ± 4.05 ?M; Ki = 101.95 ± 1.65 ?M). Molecular modeling analysis indicated that both compounds bound at the

S. Hussain; J. Gaffney; N. Ahmed; M. Slevin; M. Iqbal Choudhary; V. U. Ahmad; Z. Qasmi; M. A. Abbasi

2009-01-01

122

[Membranotropic effect of some triterpene glycosides possessing immunostimulating properties].  

PubMed

The peculiarities of the interaction between cell membrane lipids and triterpene glycosides from holothurians Apostichopus japonicus S. and Cucumaria japonica (holotoxin A1 and cucumarioside A2-2, respectively) were studied in comparison with plant saponins from Quillaja saponaria, known as hemolytic, adjuvant, and structure-forming components of immunostimulating complexes. Similar to Quillaja saponins, the sea glycosides, holotoxin A1 and cucumarioside A2-2 were shown to possess a high hemolytic activity (2.6 and 3 microg/ml, respectively) and sterol-depending membranotropic effect mediated by the formation of nonbilayer sterol-lipid-glycoside complexes. At the same time, cucumarioside A2-2 bound exogenic cholesterol only in the presence of membrane lipids, such as phosphatidylcholine or monogalactosyldiacylglycerol, in contrast to Quillaja saponins and holotoxin A1, which bound cholesterol in the molar ratios 1:2 and 1:8, respectively. Moreover, in all cases, tree-component complexes containing cholesterol, lipid, and glycoside exhibited a lower hemolytic activity compared with two-component sterol-glycoside complexes. It was concluded that the hydrophobic medium of cell membranes performs a potentiative role in the effective interaction between triterpene glycosides and "sterol receptors". A method for decreasing the toxicity of membranotropic holothurian glycosides possessing the immunomodulating properties was suggested. PMID:18634319

Lee, I A; Popov, A M; Kostetski?, E Ia; Sanina, N M; Maze?ka, A N; Boguslavski?, V M

2008-01-01

123

New iridoid glycoside from Gratiola officinalis.  

PubMed

A new iridoid glycoside, 1?,6?-di-O-trans-cinnamoyl-9-O-?-D-glucopyranosyl-3-iridene-5?-ol (1), along with four known compounds loliolide (2), ?-sitosterol-3-O-?-D-glucopyranoside (3), betulinic acid (4), and ?-amyrin (5), was isolated from the aerial parts of Gratiola officinalis L. The structure of the new compound was deduced on the basis of 1D ąH and ąłC NMR and 2D HMQC, HMBC, and COSY experiments, and mass spectrometric techniques (EI-MS and HR-EI-MS). The relative configuration of 1 was assigned by comparative analysis of the NMR spectral data with known analogs, together with NOESY experiments. PMID:23134347

Ali, Liaqat; Rizvi, Tania Shamim; Ahmad, Manzoor; Shaheen, Farzana

2012-01-01

124

New steroidal glycosides from Tribulus terrestris L.  

PubMed

Two new steroidal glycosides were isolated from Tribulus terrestris L. Their structures were elucidated as 26-O-?-D-glucopyranosyl-5?-furostan-12-one-20(22)-ene-3?,23,26-triol-3-O-?-D-xylopyranosyl-(1 ? 2)-[?-D-xylopyranosyl-(1 ? 3)]-?-D-glucopyranosyl-(1 ? 4)-[?-L-rhamnopyranosyl-(1 ? 2)]-?-D-galactopyranoside (1) and 26-O-?-D-glucopyranosyl-5?-furostan-20(22)-ene-3?,23,26-triol-3-O-?-D-xylopyranosyl-(1 ? 2)-[?-D-xylopyranosyl-(1 ? 3)]-?-D-glucopyranosyl-(1 ? 4)-[?-L-rhamnopyranosyl-(1 ? 2)]-?-D-galactopyranoside (2) by spectroscopic methods including 1D and 2D NMR experiments. PMID:22694659

Chen, Gang; Liu, Tao; Lu, Xuan; Wang, Hai-Feng; Hua, Hui-Ming; Pei, Yue-Hu

2012-01-01

125

Cytotoxic steroidal glycosides from Allium flavum.  

PubMed

Three new spirostane-type glycosides (1-3) were isolated from the whole plant of Allium flavum. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-2?-hydroxyspirost-5-en-3?-yl O-?-D-xylopyranosyl-(1?3)-[?-D-galactopyranosyl-(1?2)]-?-D-galactopyranosyl-(1?4)-?-D-galactopyranoside (1), (20S,25R)-2?-hydroxyspirost-5-en-3?-yl O-?-D-xylopyranosyl-(1?3)-[?-D-glucopyranosyl-(1?2)]-?-D-galactopyranosyl-(1?4)-?-D-galactopyranoside (2), and (20S,25R)-spirost-5-en-3?-yl O-?-L-rhamnopyranosyl-(1?4)-[?-D-glucopyranosyl-(1?2)]-?-D-glucopyranoside (3). The three saponins were evaluated for cytotoxicity against a human cancer cell line (colorectal SW480). PMID:24380693

Rezgui, Abdelmalek; Mitaine-Offer, Anne-Claire; Paululat, Thomas; Delemasure, Stéphanie; Dutartre, Patrick; Lacaille-Dubois, Marie-Aleth

2014-03-01

126

Phenolic glycosides from Symplocos racemosa: natural inhibitors of phosphodiesterase I.  

PubMed

One new phenolic glycoside named benzoylsalireposide (1) along with one known phenolic glycoside named salireposide (2) have been isolated from Symplocos racemosa. Four other known compounds i.e. beta-amyrin (3), oleonolic acid (4), beta-sitosterol (5) and beta-sitosterol glycoside (6) were also isolated from this plant. The structure elucidation of the isolated compounds was based primarily on 1D- and 2D-NMR analysis, including COSY, HMQC, and HMBC correlations. The compound 1 and 2 showed inhibitory activity against snake venom phosphodiesterase I. PMID:12711144

Ahmad, Viqar Uddin; Abbasi, Muhammad Athar; Hussain, Hidayat; Akhtar, Muhammad Nadeem; Farooq, Umar; Fatima, Naheed; Choudhary, M Iqbal

2003-05-01

127

Synthesis and sensory evaluation of ent-kaurane diterpene glycosides.  

PubMed

Catalytic hydrogenation of the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana, namely rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)? and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data and chemical studies. Also, we report herewith the sensory evaluation of all the reduced compounds against their corresponding original steviol glycosides and sucrose for the sweetness property of these molecules. PMID:22836210

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

2012-01-01

128

Steroidal glycosides from the bulbs of Ornithogalum thyrsoides.  

PubMed

Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells. PMID:15497941

Kuroda, Minpei; Mimaki, Yoshihiro; Ori, Kazutomo; Sakagami, Hiroshi; Sashida, Yutaka

2004-10-01

129

Triterpene saponins of Caltha polypetala. Glycosides G and I  

Microsoft Academic Search

From the epigeal organs of the great march marigold (family Ranunculaceae) two triterpene glycosides, a tetra- and a pentaoside of hederagenin, have been isolated. Their chemical structures have been established by chemical methods of investigation and by1H and13C NMR spectroscopy. Glycoside G is hederagenin 3-O-a-L-arabinoside 28-O-[O-a-L-rhamnopyranosyl-(1 ? 4)-O-ß-D-glucopyranosyl-(1 ? 6)-ß-D-glucopyranoside]. Glycoside I is hederagenin 3-O-[O-ß-D-glucopyranosyl-(1 ? 2)-a-L-arabinoside 28-O-[O-a-L-rhamnopyranosyl-(1 ? 4)-O-ß-D-glucopyranosyl-(1

M. M. Vugalter; G. E. Dekanosidze; O. D. Dzhikiya; A. S. Shashkov; É. P. Kemertelidze

1988-01-01

130

Lignan, phenolic and iridoid glycosides from Stereospermum cylindricum.  

PubMed

A lignan glycoside [(+)-cycloolivil 4'-O-beta-d-glucopyranoside], a phenolic glycoside [3,4-dimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside] and a iridoid glycoside (stereospermoside) were isolated from the leaves and branches of Stereospermum cylindricum, together with (+)-cycloolivil, (+)-cycloolivil 6-O-beta-d-glucopyranoside, (-)-olivil, (-)-olivil 4-O-beta-d-glucopyranoside, (-)-olivil 4'-O-beta-d-glucopyranoside, vanilloloside, decaffeoyl-verbascoside, isoverbascoside, 3,4,5-trimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside, ajugol, verminoside, and specioside. The structure elucidations were based on spectroscopic evidence. PMID:16310232

Kanchanapoom, Tripetch; Noiarsa, Pawadee; Otsuka, Hideaki; Ruchirawat, Somsak

2006-03-01

131

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

PubMed

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

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

2012-03-25

132

A new phenolic glycoside from the roots of Lygodium japonicum  

Microsoft Academic Search

A new phenolic glycoside, 3,4-dihydroxybenzoic acid 4-O-(4?-O-methyl)-?-D-glucopyranoside (1), was isolated from the roots of Lygodium japonicum. The structure was elucidated on the basis of spectroscopic methods.

Wencai Ye; Chunlin Fan; Leihong Zhang; Zhiqi Yin; Shouxun Zhao

2007-01-01

133

A new phenolic glycoside from the roots of Lygodium japonicum.  

PubMed

A new phenolic glycoside, 3,4-dihydroxybenzoic acid 4-O-(4'-O-methyl)-beta-D-glucopyranoside (1), was isolated from the roots of Lygodium japonicum. The structure was elucidated on the basis of spectroscopic methods. PMID:17570612

Ye, Wencai; Fan, Chunlin; Zhang, Leihong; Yin, Zhiqi; Zhao, Shouxun

2007-12-01

134

Steroid saponins III. Glycosides A and B from Yucca filamentosa  

Microsoft Academic Search

Summary  Two glycosides have been isolated from the roots ofYucca filamentosa L. One of them proved to be trillin, and the second — yuccoside B — 3-O-[galactopyranosyl-1(1 ? 4)-glucopyranosyl]tigogenin.

P. K. Kintya; I. P. Dragalin; V. Ya. Chirva

1972-01-01

135

3-hydroxycoumarin glycosides from Alyxia reinwardti var. Lucida.  

PubMed

Investigation of the inner bark of Alyxia reinwardti var. lucida led to the isolation of two new coumarin glycosides, 1 and 2, whose structures were determined by interpretation of their spectroscopic data, particularly NMR spectroscopy. PMID:7764154

Lin, L J; Lin, L Z; Ruangrungsi, N; Cordell, G A

1993-10-01

136

Rebaudioside F, a diterpene glycoside from Stevia rebaudiana  

Microsoft Academic Search

The sweet diterpenoid glycoside, rebaudioside F, was isolated from leaves of a high rebaudioside C producing line of Stevia rebaudiana, and its structure was established by chemical and spectral studies.

Alvin N. Starratt; Christopher W. Kirby; Robert Pocs; James E. Brandle

2002-01-01

137

Glycosides of benzyl and salicyl alcohols from Alangium chinense.  

PubMed

From the water-soluble fraction of the dried leaves of Alangium chinense, three new glycosides, benzyl alcohol beta-D-glucopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 6)]-beta-D-glucopyranoside, 2'-O-beta-D-glucopyranosylsalicin, and 2'-O-beta-D-glucopyranosyl-6'-O-beta-D-xylopyranosylsalicin were isolated along with seven known glycosides. The structures of the new compounds were determined by spectroscopic and chemical means. PMID:11605667

Itoh, A; Tanahashi, T; Nagakura, N; Inoue, K; Kuwajima, H; Wu, H X

2001-10-01

138

Two new glycosides from the florets of Carthamus tinctorius.  

PubMed

Two new glycoside compounds, named saffloquinoside C (1) and (-)-4-hydroxybenzoic acid-4-O-[6'-O-(2?-methylbutyryl)-?-D-glucopyranoside] (2), were isolated from the florets of Carthamus tinctorius. Their structures were elucidated by detailed spectroscopic means including UV, IR, HR-ESI-MS, 1D and 2D NMR, and CD data. Compound 1 was a rare quinochalcone glycoside with six five-membered dioxaspirocycle. PMID:23600648

Jiang, Jian-Shuang; Chen, Zhong; Yang, Ya-Nan; Feng, Zi-Ming; Zhang, Pei-Cheng

2013-01-01

139

[Seasonal fluctuation of flavonol glycosides in Epimedium species].  

PubMed

The seasonal fluctuation of flavonol glycosides in the leaves of Epimedium grandiflorum var. thunbergianum, E. cremeum and E. sempervirens (Berberidaceae) was investigated. The total content of glycosides was shown in the highest quantity at the flowering time, and as the leaves mature it has become stable amount with a little decrease. The suitable period for the harvest of Epimedium leaves was concluded to be two or three months after the flowering time. PMID:2760814

Mizuno, M; Iinuma, M; Tanaka, T; Iwashima, S; Sakakibara, N

1989-04-01

140

Three New Steroidal Glycosides from the Roots of Cynanchum stauntonii  

PubMed Central

Three new steroidal glycosides, named as stauntosides L, M, and N (1–3), along with one known C21 steroidal glycoside, anhydrohirundigenin monothevetoside (4), were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR, HRESI-MS, and chemical methods.

Yu, Jin-Qian; Zhang, Zhi-Hui; Deng, An-Jun; Qin, Hai-Lin

2013-01-01

141

Cardiac glycosides: Prerequisites for the development of new cardiotonic compounds  

Microsoft Academic Search

Summary Two prerequisites in a successful search for cardiac glycosides are the separability of the inotropicallyactive from the toxically-active component and knowledge of their structure-activity relationships and\\/or indispensible structural features. A number of papers show that toxic effects of heart glycosides are dependent upon inhibition of the Na+, K+-transport ATPase. This is not, however, the case with the inotropic effect,

Th. W. Güntert; H. H. A. Linde

1977-01-01

142

Reverse Algols  

NASA Technical Reports Server (NTRS)

Reverse Algols, binary systems with a semidetached configuration in which the more massive component is in contact with the critical equipotential surface, are examined. Observational evidence for reverse Algols is presented and the parameters of seven reverse Algols are listed. The evolution of Algols and reverse Algols is discussed. It is suggested that, because reverse Algols represent the premass-reversal semidetached phase of close binary evolution, the evolutionary time scale between regular and reverse Algols is the ratio of the number of confirmed systems of these two Algol types.

Leung, K. C.

1989-01-01

143

Antioxidant flavonoid glycosides from Evolvulus alsinoides.  

PubMed

Oxidative damage is an established outcome of chronic stress. Thus, the present study was designed to investigate the modulatory role of ethanolic extract of Evolvulus alsinoides (EA) in terms of oxidative alterations at peripheral and central level in rats subjected to chronic unpredictable stress (CUS). CUS exposure for 7 days reduced Cu, Zn superoxide dismutase and catalase activity with increase in glutathione peroxidase activity and lipid peroxidation, while decrease in reduced glutathione level in blood plasma, frontal cortex and hippocampus regions of brain. Oral administration of EA extract at 200mg/kg p.o. normalized these stress induced oxidative alterations with an efficacy similar to that of melatonin. Further, EA extract was taken up for detailed chemical investigation. Two new flavonol-4'-glycoside, kaempferol 4'-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (3) and kaempferol 4'-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (5) were isolated, along with eight known compounds (1, 2, 4 and 6-10). The structures of new compounds were established by detailed spectroscopic studies, while known compounds were characterized by direct comparison of their reported NMR data. All these compounds were evaluated for their in vitro antioxidant activity. Compounds 3, 5, 9 and 10 at 100 and 200 microg/ml showed significant in vitro antioxidant activity. Therefore, EA may hold great potential in preventing clinical deterioration in stress induced oxidative load and related disorders. PMID:19748554

Kumar, Manmeet; Ahmad, Ausaf; Rawat, Preeti; Khan, Mohammad Faheem; Rasheed, Naila; Gupta, Prasoon; Sathiamoorthy, B; Bhatia, Gitika; Palit, Gautam; Maurya, Rakesh

2010-06-01

144

Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis.  

PubMed

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

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

2013-10-01

145

Reverse Osmosis  

NSDL National Science Digital Library

Reverse Osmosis: In reverse osmosis, the idea is to use the membrane to act like an extremely fine filter to create drinkable water from salty (or otherwise contaminated) water. A complete explanation is here along with helpful diagrams.

2008-09-22

146

Human psychometric and taste receptor responses to steviol glycosides.  

PubMed

Steviol glycosides, the sweet principle of Stevia Rebaudiana (Bertoni) Bertoni, have recently been approved as a food additive in the EU. The herbal non-nutritive high-potency sweeteners perfectly meet the rising consumer demand for natural food ingredients in Europe. We have characterized the organoleptic properties of the most common steviol glycosides by an experimental approach combining human sensory studies and cell-based functional taste receptor expression assays. On the basis of their potency to elicit sweet and bitter taste sensations, we identified glycone chain length, pyranose substitution, and the C16 double bond as the structural features giving distinction to the gustatory profile of steviol glycosides. A comprehensive screening of 25 human bitter taste receptors revealed that two receptors, hTAS2R4 and hTAS2R14, mediate the bitter off-taste of steviol glycosides. For some test substances, e.g., stevioside, we observed a decline in sweet intensity at supra-maximum concentrations. This effect did not arise from allosteric modulation of the hTAS1R2/R3 sweet taste receptor but might be explained by intramolecular cross-modal suppression between the sweet and bitter taste component of steviol glycosides. These results might contribute to the production of preferentially sweet and least bitter tasting Stevia extracts by an optimization of breeding and postharvest downstream processing. PMID:22616809

Hellfritsch, Caroline; Brockhoff, Anne; Stähler, Frauke; Meyerhof, Wolfgang; Hofmann, Thomas

2012-07-11

147

Glycosidic Bond Cleavage is Not Required for Phytosteryl Glycoside-Induced Reduction of Cholesterol Absorption in Mice  

PubMed Central

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 tracers cholesterol-d7 and sitostanol-d4. In a three-day fecal recovery study, ASG reduced cholesterol absorption efficiency by 45 ± 6% compared with 40 ± 6% observed with PSE. Four hours after gavage, plasma and liver cholesterol-d7 levels were reduced 86% or more when ASG was present. Liver total phytosterols were unchanged after ASG administration but were significantly increased after PSE. After ASG treatment both ASG and deacylated steryl glycosides (SG) were found in the gut mucosa and lumen. ASG was quantitatively recovered from stool samples as SG. These results demonstrate that ASG reduces cholesterol absorption in mice as efficiently as PSE while having little systemic absorption itself. Cleavage of the glycosidic linkage is not required for biological activity of ASG. Phytosteryl glycosides should be included in measurements of bioactive phytosterols.

Lin, Xiaobo; Ma, Lina; Moreau, Robert A.

2012-01-01

148

Cytotoxic cardenolide glycosides from the root of Reevesia formosana.  

PubMed

Bioassay-guided fractionation of the root tissue of Reevesia formosana led to isolation of 13 cardenolide glycosides, reevesiosides A-I and epi-reevesiosides F-I. Their structures were determined by means of spectroscopic analysis and single-crystal X-ray diffraction was performed using reevesioside A. Reevesioside A, reevesioside F, and epi-reevesioside F displayed especially potent cytotoxicity against the MCF-7 and NCI-H460 cancer cell lines, with IC(50) values of 63±2 and 19±1, 72±8 and 20±0, and 34±6 and 10±1 nM, respectively. Identification of the sugar constituents and unusual 18,20-epoxide cardenolide glycosides are described herein. Cardiac glycosides were previously unknown in the Sterculiaceae family. PMID:23313131

Chang, Hsun-Shuo; Chiang, Michael Y; Hsu, Hsing-Yu; Yang, Cheng-Wei; Lin, Chu-Hung; Lee, Shiow-Ju; Chen, Ih-Sheng

2013-03-01

149

Selective hydrolysis of flavonoid glycosides by Curvularia lunata.  

PubMed

Twelve flavonoid glycosides were involved in the biotransformation of the glycosyl moieties by Curvularia lunata 3.4381, and the products were analyzed by UPLC/PDA-Q-TOF-MS(E). Curvularia lunata displayed hydrolyzing activities on the terminal Rha or Glc units of some flavonoid glycosides. Terminal Rha with a 1 ? 2 linkage of isorhamnetin-3-O-neohesperidoside and typhaneoside could be hydrolyzed by Curvularia lunata, but terminal Rha with a 1 ? 6 linkage of rutin, typhaneoside, and quercetin-3-O-apiosyl-(1 ? 2)-[rhamnosyl-(1 ? 6)]-glucoside could not be hydrolyzed. Curvularia lunata could also hydrolyze the Glc of icariin, floramanoside B, and naringin. This is the first report of the hydrolysis of glycosyl units of flavonoid glycosides by Curvularia lunata. A new way to convert naringin to naringenin was found in this research. PMID:24345511

Liu, Jing-Yuan; Yu, He-Shui; Feng, Bing; Kang, Li-Ping; Pang, Xu; Xiong, Cheng-Qi; Zhao, Yang; Li, Chun-Mei; Zhang, Yi; Ma, Bai-Ping

2013-11-01

150

Chemical and biological properties of quinochalcone C-glycosides from the florets of Carthamus tinctorius.  

PubMed

Quinochalcone C-glycosides are regarded as characteristic components that have only been isolated from the florets of Carthamus tinctorius. Recently, quinochalcone C-glycosides were found to have multiple pharmacological activities, which has attracted the attention of many researchers to explore these compounds. This review aims to summarize quinochalcone C-glycosides' physicochemical properties, chromatographic behavior, spectroscopic characteristics, as well as their biological activities, which will be helpful for further study and development of quinochalcone C-glycosides. PMID:24335575

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

2013-01-01

151

Balanitoside, a furostanol glycoside, and 6-methyldiosgenin from Balanites aegyptiaca.  

PubMed

In addition to a known spirostanol glycoside, balanitin-3, and a new sapogenol, 6-methyldiosgenin, a new furostanol saponin, balanitoside has been isolated from the fruits (mesocarp) of Balanites aegyptiaca. The structure of the glycoside has been determined as 26-O-beta-D-glucopyranosyl-3 beta, 22,26-trihydroxy-furost-5-ene 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D- glucopyranosyl-(1-->4)-beta-D-glucopyranoside, on the basis of spectroscopic and chemical evidence. PMID:1368863

Hosny, M; Khalifa, T; Cali?, I; Wright, A D; Sticher, O

1992-10-01

152

Steroidal glycosides from Reineckia carnea herba and their antitussive activity.  

PubMed

Two new steroidal glycosides, 1?,3?-dihydroxy-5?-pregn-16-en-20-one 3-O-?-L-rhamnopyranoside (1) and 1?,3?,27-trihydroxycholest-16-en-22-one 1,3-di-O-?-L-rhamnoside (2), along with seven known steroidal glycosides (3-9), were isolated from Reineckia carnea herba. Their structures were determined by detailed analysis of their 1D- and 2D-NMR and MS spectra. Compound 9 was isolated for the first time from the Reineckia genus. Except for 8, compounds 2, 3, 4, 5, 6, 7, and 9 displayed clear in vitro antitussive activity. PMID:23670621

Han, Na; Chen, Ling Li; Wang, Yao; Xue, Rui; Zou, Li Bo; Liu, Fang; Yin, Jun

2013-06-01

153

Lipoxygenase inhibiting ethyl substituted glycoside from Symplocos racemosa.  

PubMed

Phytochemical investigation of Symplocos racemosa resulted in the isolation of a new ethyl substituted glycoside, 1-ethyl brachiose-3'-acetate (1) along with four known compounds ketochaulmoogric acid (2), nonaeicosanol (3), triacontyl palmitate (4) and methyl triacontanoate (5). The substitution of ethyl group on 1 was natural because during the course of extraction and purification ethanol was not used. The structural elucidation of the isolated compounds was based primarily on 1D- and 2D-NMR analysis, including COSY, HMQC, and HMBC correlations. The glycoside 1 and triacontyl palmitate (4) displayed the inhibitory potential against lipoxygenase and urease enzyme, respectively. PMID:15938197

Abbasi, Muhammad Athar; Ahmad, Viqar Uddin; Zubair, Muhammad; Nawaz, Sarfraz A; Lodhi, Muhammad Arif; Farooq, Umar; Choudhary, M Iqbal

2005-07-01

154

Xanthone glycoside constituents of Swertia kouitchensis with ?-glucosidase inhibitory activity.  

PubMed

Ten new xanthone glycosides, kouitchensides A-J (1-10), and 11 known analogues were isolated from an n-butanol fraction of Swertia kouitchensis. The structures of these glycosides were determined on the basis of extensive spectroscopic data interpretation and comparison with data reported in the literature. In an in vitro test, compounds 2, 4, 5, 6, 11, 12, and 13 (IC50 values in the range 126 to 451 ?M) displayed more potent inhibitory effects against ?-glucosidase activity than the positive control, acarbose (IC50 value of 627 ?M). PMID:23805995

Wan, Luo-Sheng; Min, Qiu-Xia; Wang, Yong-Long; Yue, Yao-Dong; Chen, Jia-Chun

2013-07-26

155

Phenylethanoid and flavone glycosides from Ruellia tuberosa L.  

PubMed

A new phenylethanoid glycoside, isocassifolioside (8), and two new flavone glycosides, hispidulin 7-O-?-L-rhamnopyranosyl-(1'? ? 2?)-O-?-D-glucuronopyranoside (11) and pectolinaringenin 7-O-?-L-rhamnopyranosyl-(1'? ? 2?)-O-?-D-glucuronopyranoside (12) were isolated from the aerial portions of Ruellia tuberosa L., together with verbascoside (1), isoverbascoside (2), nuomioside (3), isonuomioside (4), forsythoside B (5), paucifloside (6), cassifolioside (7), hispidulin 7-O-?-D-glucuronopyranoside (9) and comanthoside B (10). The structure elucidations were based on analyses of chemical and spectroscopic data including 1D- and 2D-NMR. The isolated compounds 1-12 exhibited radical scavenging activity using ORAC assay. PMID:22447282

Phakeovilay, Chiobouaphong; Disadee, Wannaporn; Sahakitpichan, Poolsak; Sitthimonchai, Somkit; Kittakoop, Prasat; Ruchirawat, Somsak; Kanchanapoom, Tripetch

2013-01-01

156

Caucasicosides E-M, furostanol glycosides from Helleborus caucasicus.  

PubMed

Nine furostanol glycosides, namely caucasicosides E-M, were isolated from the MeOH extract of the leaves of Helleborus caucasicus, along with 11 known compounds including nine furostanol glycosides, a bufadienolide and an ecdysteroid. Their structures were established by the extensive use of 1D and 2D NMR experiments along with ESIMS(n) analyses. The steroidal composition of leaves of H. caucasicus shows as particular feature the occurrence of steroidal compounds belonging to the 5? series, unusual for Helleborus species, and in particular, caucasicosides F-H are based on a 5?-polyhydroxylated steroidal aglycon never reported before. PMID:21893324

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

2011-12-01

157

Endogenous and exogenous cardiac glycosides and their mechanisms of action.  

PubMed

Cardiac glycosides have been used for decades to treat congestive heart failure. The recent identification of cardiotonic steroids such as ouabain, digoxin, marinobufagenin, and telocinobufagin in blood plasma, adrenal glands, and hypothalamus of mammals led to exciting new perspectives in the pathology of heart failure and arterial hypertension. Biosynthesis of ouabain and digoxin occurs in adrenal glands and is under the control of angiotensin II, endothelin, and epinephrine released from cells of the midbrain upon stimulation of brain areas sensing cerebrospinal Na(+) concentration and, apparently, the body's K(+) content. Rapid changes of endogenous ouabain upon physical exercise may favor the economy of the heart by a rise of intracellular Ca(2)(+) levels in cardiac and atrial muscle cells. According to the sodium pump lag hypothesis, this may be accomplished by partial inhibition of the sodium pump and Ca(2+) influx via the Na(+)/Ca(2+) exchanger working in reverse mode or via activation of the Na(+)/K(+)-ATPase signalosome complex, generating intracellular calcium oscillations, reactive oxygen species, and gene activation via nuclear factor-kappaB or extracellular signal-regulated kinases 1 and 2. Elevated concentrations of endogenous ouabain and marinobufagenin in the subnanomolar concentration range were found to stimulate proliferation and differentiation of cardiac and smooth muscle cells. They may have a primary role in the development of cardiac dysfunction and failure because (i) offspring of hypertensive patients evidently inherit elevated plasma concentrations of endogenous ouabain; (ii) such elevated concentrations correlate positively with cardiac dysfunction, hypertrophy, and arterial hypertension; (iii) about 40% of Europeans with uncomplicated essential hypertension show increased concentrations of endogenous ouabain associated with reduced heart rate and cardiac hypertrophy; (iv) in patients with advanced arterial hypertension, circulating levels of endogenous ouabain correlate with BP and total peripheral resistance; (v) among patients with idiopathic dilated cardiomyopathy, high circulating levels of endogenous ouabain and marinobufagenin identify those individuals who are predisposed to progressing more rapidly to heart failure, suggesting that endogenous ouabain (and marinobufagenin) may contribute to toxicity upon digoxin therapy. In contrast to endogenous ouabain, endogenous marinobufagenin may act as a natriuretic substance as well. It shows a higher affinity for the ouabain-insensitive alpha(1) isoform of Na(+)/K(+)-ATPase of rat kidney tubular cells and its levels are increased in volume expansion and pre-eclampsia. Digoxin, which is synthesized in adrenal glands, seems to counteract the hypertensinogenic action of ouabain in rats, as do antibodies against ouabain, for example, (Digibind) and rostafuroxin (PST 2238), a selective ouabain antagonist. It lowers BP in ouabain- and adducin-dependent hypertension in rats and is a promising new class of antihypertensive medication in humans. PMID:17610345

Schoner, Wilhelm; Scheiner-Bobis, Georgios

2007-01-01

158

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

Microsoft Academic Search

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

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

2010-01-01

159

Hydrolysis of black soybean isoflavone glycosides by Bacillus subtilis natto.  

PubMed

Hydrolysis of isoflavone glycosides by Bacillus subtilis natto NTU-18 in black soymilk is reported. At the concentration of 3-5% (w/v), black soymilk in flask cultures, the isoflavones, daidzin, and genistin were highly deglycosylated within 24 h. Deglycosylation of isoflavones was further carried out in a 7-l fermenter with 5% black soymilk. During the fermentation, viable cells increased from 10(3) to 10(9) CFU ml(-1) in 15 h, and the activity of beta-glucosidase appeared at 8 h after inoculation and reached a maximum (3.3 U/ml) at 12 h, then decreased rapidly. Deglycosylation of isoflavone glycosides was observed at the same period, the deglycosylation rate of daidzin and genistin at 24 h was 100 and 75%, respectively. It is significantly higher than the previous reports of fermentation with lactic acid bacteria. In accordance with the deglycosylation of isoflavone glycosides, the estrogenic activity of the 24 h fermented black soymilk for ERbeta estrogen receptor increased to threefold; meanwhile, the fermented broth activated ERalpha estrogen receptor to a less extent than ERbeta. These results suggest that this fermentation effectively hydrolyzed the glycosides from isoflavone in black soymilk and the fermented black soymilk has the potential to be applied to selective estrogen receptor modulator products. PMID:16715232

Kuo, Lun-Cheng; Cheng, Wei-Yi; Wu, Ren-Yu; Huang, Ching-Jang; Lee, Kung-Ta

2006-11-01

160

Lipoxygenase inhibiting ethyl substituted glycoside from Symplocos racemosa  

Microsoft Academic Search

Phytochemical investigation of Symplocos racemosa resulted in the isolation of a new ethyl substituted glycoside, 1-ethyl brachiose-3?-acetate (1) along with four known compounds ketochaulmoogric acid (2), nonaeicosanol (3), triacontyl palmitate (4) and methyl triacontanoate (5). The substitution of ethyl group on 1 was natural because during the course of extraction and purification ethanol was not used. The structural elucidation of

Muhammad Athar Abbasi; Viqar Uddin Ahmad; Muhammad Zubair; Sarfraz A. Nawaz; Muhammad Arif Lodhi; Umar Farooq; M. Iqbal Choudhary

2005-01-01

161

New glycosides of acetophenone derivatives and phenylpropanoids from Juniperus occidentalis.  

PubMed

New glycosides of seven acetophenone derivatives (1-7) and two phenylpropanoids (8, 9), named juniperosides III-XI, have been isolated from the MeOH extract of the leaves and stems of Juniperus occidentalis Hook. (Cupressaceae), together with eleven other known compounds. The structures of these compounds have been successfully elucidated using a variety of spectroscopic techniques. PMID:22847379

Inatomi, Yuka; Murata, Hiroko; Inada, Akira; Nakanishi, Tsutomu; Lang, Frank A; Murata, Jin; Iinuma, Munekazu

2013-04-01

162

Glycosidic constituents from the roots and rhizomes of Melicope pteleifolia.  

PubMed

Seven new diglycosidic constituents, named pteleifosides A-G (1-7), along with ten known glycosides, were isolated from the roots and rhizomes of Melicope pteleifolia (Champ. ex Benth.) T. Hartley. The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. PMID:23010492

Zhang, Yang; Yang, Li-Jun; Jiang, Kun; Tan, Chang-Heng; Tan, Jun-Jie; Yang, Pei-Ming; Zhu, Da-Yuan

2012-11-01

163

Hydroxycinnamoyl ester glycosides and saponins from flowers of Verbascum phlomoides.  

PubMed

A new iridoid ester glycoside acylated with p-coumaric acid was isolated from the flowers of Verbascum phlomoides, together with one known one, specioside. Caffeic acid esters, verbascoside and forsythoside B were found as minor constituents. A new saponin was also obtained and identified as desrhamnosylverbascosaponin. PMID:8987909

Klimek, B

1996-12-01

164

Two new flavonol glycosides from Gymnema sylvestre and Euphorbia ebracteolata  

Microsoft Academic Search

Two new flavonol glycosides, namely kaempferol 3-O-?-d-glucopyranosyl-(1?4)-?-l-rhamnopyranosyl-(1?6)-?-d-galactopyranoside (1) and quercetin 3-O-6?-(3-hydroxyl-3-methylglutaryl)-?-d-glucopyranoside (2), have been isolated from the aerial parts of Gymnema sylvestre and Euphorbia ebracteolata, respectively. Their structures were determined on the basis of chemical and spectroscopic methods.

Xin Liu; Wencai Ye; Biao Yu; Shouxun Zhao; Houming Wu; Chuntao Che

2004-01-01

165

On the differences between ouabain and digitalis glycosides.  

PubMed

Digoxin and digitoxin are widely used in the treatment of heart diseases. The exact mechanism of action of these drugs has remained an enigma. Ouabain has become the standard tool to investigate the mode of action of cardiotonic steroids, and results with ouabain are regarded as generally valid for all cardiac glycosides. However, there are marked differences between the effects of ouabain and digitalis glycosides. Ouabain has a different therapeutic profile from digitalis derivatives. Unlike digitalis glycosides, ouabain has a fast onset of action and stimulates myocardial metabolism. The inotropic effect of cardiotonic steroids is not related to inhibition of the Na-K-ATPase. Ouabain and digitalis derivatives develop their effects in different cellular spaces. Digitalis glycosides increase the intracellular calcium concentration by entering the cell interior and acting on the ryanodine receptors and by forming transmembrane calcium channels. Ouabain, by activation of the Na-K-ATPase from the extracellular side, triggers release of calcium from intracellular stores via signal transduction pathways and activates myocardial metabolism. These data no longer support the concept that all cardiotonic steroids exhibit their therapeutic effects by partial inhibition of the ion-pumping function of the Na-K-ATPase. Hence, it is suggested that this deeply rooted dogma be revised. PMID:21642827

Fuerstenwerth, Hauke

2014-01-01

166

Sesquiterpene lactone glycosides from the roots of Ferula varia.  

PubMed

Seven new sesquiterpene lactone glycosides (1-7) were isolated from the H2O-soluble fraction from the MeOH extract of the roots of Ferula varia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of compounds 1 and 2 were determined by modified Mosher's method. PMID:22790827

Kurimoto, Shin-ichiro; Suzuki, Kyoko; Okasaka, Mamoru; Kashiwada, Yoshiki; Kodzhimatov, Olimjion Kakhkharovich; Takaishi, Yoshihisa

2012-01-01

167

Hydrolytical instability of hydroxyanthraquinone glycosides in pressurized liquid extraction.  

PubMed

Hydroxyanthraquinones represent a group of pharmacologically active compounds characteristic for plants of the Rumex and Rheum genera. These compounds in the human intestine act as laxative compounds. As they cause the greatest side effects and are often abused by the public, their accurate analysis in plants and plant-derived laxatives is much needed. To isolate compounds from plants, pressurized liquid extraction (PLE) is frequently applied. The technique has been regarded, so far, as very effective, even in isolation of sensitive compounds for which exposure time in high temperature has a negative impact. This work demonstrates some interesting and surprising results accompanying PLE of hydroxyanthraquinones from the Rumex crispus L. root using methanol/water mixtures as extractant. The presented results demonstrate that glycoside forms of hydroxyanthraquinones (emodin-8-O-?-D-glucopyranoside, chrysophanol-8-O-?-D-glucopyranoside, and physcion-8-O-?-D-glucopyranoside) are hydrolytically unstable even in the short-lasting PLE. The increase of water concentration in the extractant leads to the increase of the transformation degree of the glycoside forms to the corresponding aglycones (emodin, chrysophanol, and physcion), increasing the concentration of the latter. The rise in the PLE temperature accelerates the hydrolytical degradation of the glycoside forms. The extension of the extraction time also intensifies this process. The presented results show that extraction of glycosides using extractants containing water can lead to false conclusions about the chemical composition of plants. PMID:24652155

Wianowska, Dorota

2014-05-01

168

Absorption, metabolism and elimination of strophanthus glycosides in man  

Microsoft Academic Search

In 33 healthy male volunteers, given a single oral and intravenous dose of cymarin (k-strophanthin-a), k-strophanthoside (k-strophanthin-?) and ouabain (g-strophanthin), enteral absorption and renal excretion of these glycosides and their metabolites were investigated by radioimmunoassay and HPLC.

H. Strobach; K. E. Wirth; K. Rojsathaporn

1986-01-01

169

Glycosidation of Methanol with Ribose: An Interdisciplinary Undergraduate Laboratory Experiment  

ERIC Educational Resources Information Center

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…

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

2010-01-01

170

A New Flavanonol Glycoside from Adansonia digitata Roots.  

PubMed

A new flavanonol glycoside isolated from the roots of Adansonia digitata has been characterised as 3,7-dihydroxy flavan-4-one-5-O-beta- D-galactopyranosyl (1 --> 4)-beta- D-glucopyranoside on the basis of degradation, spectral and chemical studies. PMID:17340272

Chauhan, J S; Kumar, S; Chaturvedi, R

1984-02-01

171

Curation of characterized glycoside hydrolases of Fungal origin  

PubMed Central

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/

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

2011-01-01

172

The direct action of cardiac glycosides on the kidneys  

Microsoft Academic Search

Cardiac glycosides exhibit a diuretic as well as a cardiotonic activity. The former is considered to be derived from the eardiotonic effect which brings about an improvement in hemodynamics and resutts in an increase in glomerula filtration and diuresis [1, 6, 10]. However ~, the data given by various authors are not in agreement wi~h this idea. Thus, in heart-

B. A. Pakhmurny; V. V. Parin

1965-01-01

173

Two new glycosidic acids, multifidinic acids F and G, of the ether-insoluble resin glycoside (convolvulin) from the seeds of Quamoclit × multifida.  

PubMed

Two new glycosidic acids, multifidinic acids F and G, were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction from the seeds of Quamoclit × multifida (syn. Q. sloteri House, Convolvulaceae), a hybrid between Q. pennata and Q. coccinea. The two compounds are the third and fourth examples of bisdesmosides of glycosidic acids having sugar linkages at C-3 of 3,11-dihydroxytetradecanoic acid (ipurolic acid) as well as at C-11. PMID:23271665

Ono, Masateru; Akiyama, Kousuke; Kishida, Makiko; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Miyahara, Kazumoto

2013-10-01

174

Reverse Logistics  

Microsoft Academic Search

Environmental concerns and rapid development of e-commerce bring a new focused field in reverse logistics. In order to avoid return losses and add customerspsila value, there is a need for companies to find proper ways to reduce wastes and recover the value from used products for further utilities. All these challenges make reverse logistics a contemporary area of interest among

Chaihou Zhao; Weiming Liu; Bei Wang

2008-01-01

175

Vasectomy reversal  

Microsoft Academic Search

Although vasectomy remains a popular method of contraception, the number of men requesting reversal has risen dramatically.\\u000a The microsurgical Techniques described in this article have yielded excellent results.

Roy A. Brandell; Marc Goldstein

2000-01-01

176

Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii.  

PubMed

From the water soluble fraction of the dried fruits of Alangium lamrckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-O-methyl-N-deacetylisoipecosidic acid, 7-O-methyl-N-deacetylisoipecosidic acid, 6,7-di-O-methyl-N-deacetylisoipecosidic acid and 6"-O-alpha-D-glucopyranosyl-6-O-methyl-N-deacetylisoipecosidic acid, and an iridoid glycoside, 6'-O-alpha-D-glucopyranosylloganic acid, were isolated, together with six known compounds. The structures of the previously unknown compounds were determined by spectroscopic and chemical means. The significance of these glucosides in the biogenesis of Alangium alkaloids is discussed; 6-O-methyl-N-deacetylisoipecosidic acid was also chemically converted into 10-O-demethylprotoemetine and dihydroisoalangine. PMID:11281140

Itoh, A; Tanahashi, T; Tabata, M; Shikata, M; Kakite, M; Nagai, M; Nagakura, N

2001-03-01

177

Gilvocarcin HE: a new polyketide glycoside from Streptomyces sp.  

PubMed

A new antimicrobial polyketide glycoside (1) and three known compounds, gilvocarcins H (2), V (3) and M (4) were isolated from the ethyl acetate extract of Streptomyces sp. QD01-2. The structure of (1) was established by spectroscopic analysis, X-ray single crystal diffraction and CD spectra. The new compound (1) showed potent antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Candida albicans, with MIC values of 0.5-5.0??M. Compound (1) also showed weak cytotoxicity against the MCF-7, K562 and P388 cell lines, with IC(50) values of 36, 39 and 45??M, respectively. The results showed that the vinyl side chain helps to increase the cytotoxicity and antimicrobial activities of gilvocarcin-type glycosides. In addition, the NMR data of gilvocarcin H (2) were also reported for the first time. PMID:22854339

Hou, Jiabo; Liu, Peipei; Qu, Haijun; Fu, Peng; Wang, Yi; Wang, Zhiying; Li, Ye; Teng, Xiancun; Zhu, Weiming

2012-10-01

178

Malonylated flavonol glycosides from the petals of Clitoria ternatea.  

PubMed

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

Kazuma, Kohei; Noda, Naonobu; Suzuki, Masahiko

2003-01-01

179

Coumarins of Matricaria chamomilla L.: aglycones and glycosides.  

PubMed

The identity and quantity of coumarin-like compounds in leaves and anthodia of Matricaria chamomilla L. were studied by LC-DAD and NMR. So far, two monosubstituted coumarins, herniarin and umbelliferone, and two herniarin precursors were identified therein. In this paper, two other coumarin glycosides and one aglycone were confirmed. Skimmin (umbelliferone-7-O-?-d-glucoside), daphnin (daphnetin-7-O-?-d-glucoside) and daphnetin (7,8-dihydroxycoumarin) were found for the first time in diploid and tetraploid leaves and anthodia of M. chamomilla L. Daphnetin is known as a strong sensitizer, so this compound and its glycosidic derivative can contribute to the allergic potential of chamomile. Commercial chamomile preparations were tested for their presence. PMID:23768326

Petru?ová-Poracká, Veronika; Rep?ák, Miroslav; Vilková, Mária; Imrich, Ján

2013-11-01

180

Two spirostan steroid glycoside fatty esters from Dioscorea cayenensis.  

PubMed

Two new fatty acid-spirostan steroid glycoside esters, progenin III palmitate (1) and progenin III linoleate (2), were isolated from the MeOH extract of Dioscorea cayenensis rhizomes. The extract also yielded seven previously known spirostan and furostan steroid glycosides (3-9). The structures of the new compounds were established as (25R)-spirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-[6-O-palmitoyl]-O-beta-D-glucopyranoside (1) and (25R)-spirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-[6-O-linoleoyl]-O-beta-D-glucopyranoside (2) by chemical and spectroscopic methods, including 1D and 2D NMR. The known compounds were identified as progenin III (3), dioscin (4), deltonin (5), asperin (6), gracillin (7), protodioscin (8)], and methyl protodioscin (9). PMID:23678801

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

2013-03-01

181

New monocyclic monoterpenoid glycoside from Mentha haplocalyx Briq.  

PubMed

Two new monocyclic monoterpenoid glycosides, rel-(1R,2S,3R,4R) p-menthane-1,2,3-triol 3-O-?-D-glucopyranoside (1) and rel- (1S,2R,3S) terpinolene-1,2,3-triol 3-O-?-D-glucopyranoside (2) were isolated from aqueous acetone extract of the aerial parts of Mentha haplocalyx Briq.. Their structures were elucidated through spectral analysis using MS and NMR spectrometers. PMID:22559003

She, Gai-Mei; Xu, Chao; Liu, Bin

2012-01-01

182

Hydrolysis of black soybean isoflavone glycosides by Bacillus subtilis natto  

Microsoft Academic Search

Hydrolysis of isoflavone glycosides by Bacillus subtilis natto NTU-18 in black soymilk is reported. At the concentration of 3–5% (w\\/v), black soymilk in flask cultures, the isoflavones, daidzin, and genistin were highly deglycosylated within 24 h. Deglycosylation of isoflavones was further carried out in a 7-l fermenter with 5% black soymilk. During the fermentation, viable cells increased from 103 to 109 CFU

Lun-Cheng Kuo; Wei-Yi Cheng; Ren-Yu Wu; Ching-Jang Huang; Kung-Ta Lee

2006-01-01

183

Phenolic glycosides from the leaves of Alangium platanifolium var. platanifolium.  

PubMed

Chemical investigation of Alangium platanifolium var. platanifolium has resulted in the isolation of nine phenolic glycosides that were identified by means of 1D and 2D NMR experiments. Among them, catechol and salicinol O- and 1-O-beta-D-(6-O-beta-D-apiofuranosyl)glucopyranosides, respectively 1 and 2, and two compounds characterized as adducts of 2, 6-dihydroxybenzoic acid with salicin (plataplatanoside, 3) and 4-hydroxysalicin (4-hydroxyalangifolioside, 4) were determined structurally as new compounds. PMID:11076566

Tamaki, A; Ide, T; Otsuka, H

2000-10-01

184

Phenylpropanoid glycosides from the leaves of Paulownia coreana.  

PubMed

Study on the water soluble fraction from the leaves of Paulownia coreana led to the isolation of verbascoside (1), isoverbascoside (2), campneoside II (3), and a new phenylpropanoid glycoside, (R,S)-7-hydroxy-7-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl(1 --> 3)-beta-d-(6-O-caffeoyl)-glucopyranoside (4). The structures of these compounds were established on the basis of spectroscopic evidence. PMID:18266154

Kim, Jin-Kyu; Si, Chuan-Ling; Bae, Young-Soo

2008-02-15

185

New monocyclic monoterpenoid glycoside from Mentha haplocalyx Briq.  

PubMed Central

Two new monocyclic monoterpenoid glycosides, rel-(1R,2S,3R,4R) p-menthane-1,2,3-triol 3-O-?-D-glucopyranoside (1) and rel- (1S,2R,3S) terpinolene-1,2,3-triol 3-O-?-D-glucopyranoside (2) were isolated from aqueous acetone extract of the aerial parts of Mentha haplocalyx Briq.. Their structures were elucidated through spectral analysis using MS and NMR spectrometers.

2012-01-01

186

Cucurbitane glycosides from unripe fruits of Siraitia grosvenori.  

PubMed

Studies on the constituents of the unripe fruits of Siraitia grosvenori led to the isolation of three new cucurbitane triterpene glycosides, 11-oxomogroside III (10), 11-dehydroxymogroside III (11), and 11-oxomogroside IV A (12). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods. All of the compounds isolated from the unripe fruits of S. grosvenori were tested for cytotoxic activities against tumor cells, HCT-116 and SMMC-7721. PMID:17603208

Li, Dianpeng; Ikeda, Tsuyoshi; Nohara, Toshihiro; Liu, Jinlei; Wen, Yongxin; Sakamoto, Tatsunori; Nonaka, Gen-Ichiro

2007-07-01

187

A Glycosidation Reaction Employing Montmorillonite K-10 as Catalyst  

NASA Astrophysics Data System (ADS)

The large number of biology majors and prehealth students enrolled in Organic Chemistry makes it desirable to have laboratories that involve biologically interesting molecules. Although many laboratory manuals contain sections on carbohydrate chemistry, the experiments are typically limited to esterification or hydrolysis reactions. A recent publication (Toshima, K.; Ishizuka, T.; Matsuo, G.; Nakata, M. Synlett. 1995, 306. ) on the glycosidation of glycals offered a different possibility.

Bedell, Brooke L.; Crouch, R. David; Holden, Michael S.; Martinson, Heidi E.

1996-11-01

188

A new triterpene glycoside from the roots of Symphytum officinale.  

PubMed

Chemical investigation of the EtOH-soluble portion of Symphytum officinale roots has resulted in the isolation of a new pentacyclic triterpene glycoside of oleanolic acid. Its structure was elucidated by spectroscopic studies, including 2D nmr, and chemical evidences as 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-alpha-L -arabinopyranosyl]-oleanolic acid [1]. PMID:8482944

Ahmad, V U; Noorwala, M; Mohammad, F V; Sener, B

1993-03-01

189

Relative antioxidant activity of soybean isoflavones and their glycosides  

Microsoft Academic Search

The present study compared the antioxidant potency of genistein and daidzein with their corresponding glycosides isolated from soybean seeds. The antioxidant activity was assessed using three methods, namely human low-density lipoprotein (LDL) oxidation, the ferric reducing-antioxidant power (FRAP) and the anti-DPPH free radical assays. It was found that soybean was rich in genistein and daidzein but they were present mainly

Chung Hung Lee; Lin Yang; Jin Ze Xu; Sai Ying Venus Yeung; Yu Huang; Zhen-Yu Chen

2005-01-01

190

A novel bioactive flavonol glycoside from Teramnus labialis spreng.  

PubMed

A novel biologically active flavonol glycoside (1), C26H28O17, m.p. 216-217 degrees C, was isolated from the chloroform soluble fraction of the ethanol extract of the stems of Teramnus labialis. Its structure was characterized as 3,5,7,3',4',5'-hexahydroxyflavone-3-O-beta-D-glucopyranosyl(1-->3)-O-alpha-L-arabinopyranoside by spectral analysis. The chloroform extract of compound (1) showed antibacterial and antifungal activities. PMID:15595611

Yadava, R N; Jain, Shivani

2004-12-01

191

Ex Vivo Activity of Cardiac Glycosides in Acute Leukaemia  

Microsoft Academic Search

BackgroundDespite years of interest in the anti-cancerous effects of cardiac glycosides (CGs), and numerous studies in vitro and in animals, it has not yet been possible to utilize this potential clinically. Reports have demonstrated promising in vitro effects on different targets as well as a possible therapeutic index\\/selectivity in vitro and in experimental animals. Recently, however, general inhibition of protein

Helene Hallböök; Jenny Felth; Anna Eriksson; Mĺrten Fryknäs; Lars Bohlin; Rolf Larsson; Joachim Gullbo; Irina Agoulnik

2011-01-01

192

Two acylated diarylheptanoid glycosides from red alder bark  

PubMed

Two novel acylated diarylheptanoid glycosides, oregonosides A and B (3, 4, respectively), were isolated from red alder bark and their structures established by spectrometric techniques. The compounds were identified as (5S)-1,7-bis(3, 4-dihydroxyphenyl)-5-O-(6-O-benzoyl-beta-D-glucopyranosyl)-heptan-3-o ne and (5S)-1,7-bis(3, 4-dihydroxyphenyl)-5-O-(6-O-vanilloyl-beta-D-glucopyranosyl)-heptan-3 -one. PMID:9784172

Gonzalez-Laredo; Helm; Chen; Karchesy

1998-10-01

193

A new C 21-steroidal glycoside from Cynanchum stauntonii  

Microsoft Academic Search

A new C21-steroidal glycoside with two known compounds were isolated from the root of Cynanchum Stauntonii. Based on the spectral analysis, including MS, 1H NMR, 13C NMR, DEPT, 1H–1H COSY, 13C–1H COSY, HMQC and HMBC, their chemical structures were determinated as glaucogenin-C 3-O-?-l-cymaropyranosyl-(1?4)-?-d-digitoxopyranosyl-(1?4)-?-d-canaropyranoside (1), stigmasterol (2) and ursolic acid (3).

Mei Hong Fu; Zhu Ju Wang; Hong Jun Yang; Mayila Maimai; Jing Fang; Li Ying Tang; Lan Yang

2007-01-01

194

Inhibitory effects of Thai plants ?-glycosides on Trichomonas vaginalis  

Microsoft Academic Search

Trichomoniasis is now an important health problem in developing countries. Although metronidazole has so far been widely used\\u000a to treat this disease, the prevalence of metronidazole-resistant protozoa and unpleasant adverse effects have been found.\\u000a In this study, natural products purified from Thai plants were, therefore, investigated for their effectiveness against Trichomonas vaginalis. The minimal inhibitory concentrations for all ?-glycosides against

Dumrongkiet Arthan; Somphong Sithiprom; Kanthinich Thima; Chutima Limmatvatirat; Porntip Chavalitshewinkoon-Petmitr; Jisnuson Svasti

2008-01-01

195

Three new homoisoflavanone glycosides from the bulbs of Ornithogalum caudatum.  

PubMed

Phytochemical examination of Ornithogalum caudatum led to the isolation of three new homoisoflavanone glycosides. Their structures were elucidated, on the basis of the spectroscopic data and chemical evidence and by comparing them with those of known compounds, as (-)-7-O-methyleucomol 5-O-beta-D-glucopyranoside (1), (-)-7-O-methyleucomol 5-O-beta-rutinoside (2), and (-)-7-O-methyleucomol 5-O-beta-neohesperidoside (3), respectively. PMID:11858761

Tang, Yuping; Yu, Biao; Hu, Jie; Wu, Tao; Hui, Hongzheng

2002-02-01

196

Toxicological evaluation of the isoflavone puerarin and its glycosides  

Microsoft Academic Search

Puerarin, an isoflavone derived from kudzu roots, has strong biological activities. However, its bioavailability in vivo is\\u000a often limited by its insolubility. A novel transglycosylase increases the solubility of puerarin >100-fold, by converting\\u000a it to puerarin glycosides. Since over-consumption of an isoflavone might have toxic effects, therefore, we investigated the\\u000a potential antimutagenic activity, bone marrow micronucleus test, and a 28-day

Hyuk Jin Chung; Mi Ja Chung; Soung-Jin Houng; Jungae Jeun; Dong-Keon Kweon; Chung Hyo Choi; Jong-Tae Park; Kwan-Hwa Park; Sung-Joon Lee

2009-01-01

197

Hydrolysis of grape glycosides by enological yeast ?-glucosidases  

Microsoft Academic Search

Three enological yeast strains, belonging to the speciesDebaryomyces hansenii, Debaryomyces polymorphus, andSaccharomyces cerevisiae, characterized by an exocellular ?-glucosidase activity, were examined for their ability to hydrolize a glycosidic extract from grape juice. The enzymatic preparations (culture supernant fluid) of the different yeasts released different amounts of terpenols such as linalol, ?-terpineol, geraniol, nerol, citronellol and benzyl and 2-phenylethyl alcohol. The

I. Rosi; P. Domizio; M. Vinella; M. Salicone

1995-01-01

198

One-pot hydrothermal synthesis of peony-like Ag/Ag0.68V2O5 hybrid as high-performance anode and cathode materials for rechargeable lithium batteries  

NASA Astrophysics Data System (ADS)

A peony-like Ag/Ag0.68V2O5 hybrid assembled from nanosheets with the thickness of 40 nm was synthesized through a one-pot hydrothermal approach from vanadium pentoxide (V2O5), oxalic acid (H2C2O4), and silver nitrate (AgNO3) at 180 °C for 24 h. The hybrid exhibits high performance as both anode and cathode materials for rechargeable lithium batteries. Electrochemical measurements revealed that the as-prepared Ag/Ag0.68V2O5 hybrid displayed excellent cycling stability, especially as an anode material. The resulting anode retains 100% of the initial capacity after 1000 cycles under a current density of 400 mA g-1. This phenomenon may be attributed to electron conductivity improvement by the existence of metallic silver in the hybrid in addition to the convenient access to lithium ion ingress/egress because of its unique structure.A peony-like Ag/Ag0.68V2O5 hybrid assembled from nanosheets with the thickness of 40 nm was synthesized through a one-pot hydrothermal approach from vanadium pentoxide (V2O5), oxalic acid (H2C2O4), and silver nitrate (AgNO3) at 180 °C for 24 h. The hybrid exhibits high performance as both anode and cathode materials for rechargeable lithium batteries. Electrochemical measurements revealed that the as-prepared Ag/Ag0.68V2O5 hybrid displayed excellent cycling stability, especially as an anode material. The resulting anode retains 100% of the initial capacity after 1000 cycles under a current density of 400 mA g-1. This phenomenon may be attributed to electron conductivity improvement by the existence of metallic silver in the hybrid in addition to the convenient access to lithium ion ingress/egress because of its unique structure. Electronic supplementary information (ESI) available. See DOI: 10.1039/c4nr00250d

Wei, Denghu; Li, Xiaona; Zhu, Yongchun; Liang, Jianwen; Zhang, Kailong; Qian, Yitai

2014-04-01

199

Oleanane and taraxerane glycosides from the roots of Gomphrena macrocephala.  

PubMed

Phytochemical screening of the roots of Gomphrena macrocephala, with particular attention to its triterpene glycoside constituents, has resulted in the isolation of two new oleanane glycosides (1 and 2) and a new taraxerane glycoside (3). The structures of 1-3 were determined as 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]olean-28,13-olide (1), 11alpha,12alpha-epoxy-3beta-[(O-beta-D-galactopyranosyl-(1-->3)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl)-oxy]olean-28,13-olide (2), and 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester (3), respectively, on the basis of their spectroscopic data and the results of hydrolysis. The aglycones (1a and 3a) of 1-3 with an epoxy group showed cytotoxic activity against HSC-2 human oral squamous carcinoma cells. PMID:17125230

Kuroda, Minpei; Aoshima, Taku; Haraguchi, Mitsue; Young, Maria Claudia Marx; Sakagami, Hiroshi; Mimaki, Yoshihiro

2006-11-01

200

Glycosidically bound flavor compounds of cape gooseberry (Physalis peruviana L.).  

PubMed

The bound volatile fraction of cape gooseberry (Physalis peruviana L.) fruit harvested in Colombia has been examined by HRGC and HRGC-MS after enzymatic hydrolysis using a nonselective pectinase (Rohapect D5L). Forty bound volatiles could be identified, with 21 of them being reported for the first time in cape gooseberry. After preparative isolation of the glycosidic precursors on XAD-2 resin, purification by multilayer coil countercurrent chromatography and HPLC of the peracetylated glycosides were carried out. Structure elucidation by NMR, ESI-MS/MS, and optical rotation enabled the identification of (1S,2S)-1-phenylpropane-1,2-diol 2-O-beta-D-glucopyranoside (1) and p-menth-4(8)-ene-1,2-diol 1-O-alpha-L-arabinopyranosyl-(1-6)-beta-D-glucopyranoside (2). Both glycosides have been identified for the first time in nature. They could be considered as immediate precursors of 1-phenylpropane-1,2-diol and p-menth-4(8)-ene-1,2-diol, typical volatiles found in the fruit of cape gooseberry. PMID:11308344

Mayorga, H; Knapp, H; Winterhalter, P; Duque, C

2001-04-01

201

Naturally occurring phenylethanoid glycosides: potential leads for new therapeutics.  

PubMed

Natural products have long been regarded as excellent sources for drug discovery given their structure diversity and wide variety of biological activities. Phenylethanoid glycosides are naturally occurring compounds of plant origin and are structurally characterized with a hydroxyphenylethyl moiety to which a glucopyranose is linked through a glycosidic bond. To date several hundred compounds of this type have been isolated from medicinal plants and further pharmacological studies in vitro or in vivo have shown that these compounds possess a broad array of biological activities including antibacterial, antitumor, antiviral, anti-inflammatory, neuro-protective, antioxidant, hepatoprotective, immunomodulatory, and tyrosinase inhibitory actions. Given their extensive activity profile, structure-activity relationships analyses of these compounds have been performed in a number of studies to reveal potential leads for future drug design. This article will summarize the major developments in phenylethanoid glycosides-based research in the past decade. The progresses made in phytochemistry and biological activity studies of these compounds will be reviewed. Particular attention will be given to the novel structures identified to date and the prominent therapeutic values associated with these molecules. PMID:18855681

Fu, Guangmiao; Pang, Haihong; Wong, Yung H

2008-01-01

202

Effect of cardiac glycosides on action potential characteristics and contractility in cat ventricular myocytes: role of calcium overload.  

PubMed

There is increasing evidence that cardiac glycosides act through mechanisms distinct from inhibition of the sodium pump but which may contribute to their cardiac actions. To more fully define differences between agents indicative of multiple sites of action, we studied changes in contractility and action potential (AP) configuration in cat ventricular myocytes produced by six cardiac glycosides (ouabain, ouabagenin, dihydroouabain, actodigin, digoxin, and resibufogenin). AP shortening was observed only with ouabain and actodigin. There was extensive inotropic variability between agents, with some giving full inotropic effects before automaticity occurred whereas others produced minimal inotropy before toxicity. AP shortening was not a result of alterations in calcium current or the inward rectifier potassium current, but correlated with an increase in steady-state outward current (Iss), which was sensitive to KB-R7943, a Na+-Ca2+ exchange (NCX) inhibitor. Interestingly, Iss was observed following exposure to ouabain and dihydroouabain, suggesting that an additional mechanism is operative with dihydroouabain that prevents AP shortening. Further investigation into differences in inotropy between ouabagenin, dihydroouabain and ouabain revealed almost identical responses under AP voltage clamp. Thus all agents appear to act on the sodium pump and thereby secondarily increase the outward reverse mode NCX current, but the extent of AP duration shortening and positive inotropy elicited by each agent is limited by development of their toxic actions. The quantitative differences between cardiac glycosides suggest that mechanisms independent of sodium pump inhibition may result from an altered threshold for calcium overload possibly involving direct or indirect effects on calcium release from the sarcoplasmic reticulum. PMID:12954807

Ruch, Stuart R; Nishio, Manabu; Wasserstrom, J Andrew

2003-10-01

203

Optimization and validation of a high-performance liquid chromatography method for the analysis of cardiac glycosides in Digitalis lanata.  

PubMed

In this study, a simple and reliable HPLC method for the qualitative and quantitative analysis of cardiac glycosides in Digitalis lanata Ehrh. raw material was developed and applied to healthy and phytoplasma-infected plants. The target analytes cover a broad range of secondary metabolites, including primary, secondary and tertiary glycosides and the corresponding aglycones. The sample preparation was carried out by sonication of the plant material with 70% (v/v) aqueous methanol at room temperature, followed by reversed-phase solid-phase extraction purification from interfering pigments. The HPLC analyses were performed on a Symmetry C(18) column (75 mm x 4.6mm I.D., 3.5 microm), with a gradient elution composed of water and acetonitrile, at a flow rate of 1.0 mL/min. The column temperature was set at 20 degrees C and the photodiode array detector monitored the eluent at 220 nm. The method was validated with respect to ICH guidelines and the validation parameters were found to be highly satisfactory. The application of the method to the analysis of D. lanata leaves indicated that air-drying was the optimum method for raw material processing when compared with freeze-drying. The analysis of healthy and phytoplasma-infected plants demonstrated that the secondary metabolite mainly affected by the pathogen presence was lanatoside C (153.2 microg/100mg versus 76.1 microg/100mg). Considering the importance of D. lanata plant material as source of cardiac glycosides, the developed method can be considered suitable for the phytochemical analysis and for the quality assurance of D. lanata used for pharmaceutical purpose. PMID:19268961

Pellati, Federica; Bruni, Renato; Bellardi, Maria Grazia; Bertaccini, Assunta; Benvenuti, Stefania

2009-04-10

204

Taxifolin Glycoside Blocks Human ether-a-go-go Related Gene K+ Channels  

PubMed Central

Taxifolin glycoside is a new drug candidate for the treatment of atopic dermatitis (AD). Many drugs cause side effects such as long QT syndrome by blocking the human ether-a-go-go related gene (hERG) K+ channels. To determine whether taxifolin glycoside would block hERG K+ channels, we recorded hERG K+ currents using a whole-cell patch clamp technique. We found that taxifolin glycoside directly blocked hERG K+ current in a concentration-dependent manner (EC50=9.6±0.7 µM). The activation curve of hERG K+ channels was negatively shifted by taxifolin glycoside. In addition, taxifolin glycoside accelerated the activation time constant and reduced the onset of the inactivation time constant. These results suggest that taxifolin glycoside blocks hERG K+ channels that function by facilitating activation and inactivation process.

Yun, Jihyun; Bae, Hyemi; Choi, Sun Eun; Kim, Jung-Ha; Choi, Young Wook; Lim, Inja; Lee, Chung Soo; Lee, Min Won; Ko, Jae-Hong; Seo, Seong Jun

2013-01-01

205

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

PubMed Central

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.

2010-01-01

206

Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides  

Microsoft Academic Search

This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates\\u000a that demonstrate different biological activities. They are of great interest, especially for the medicinal and\\/or pharmaceutical\\u000a industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as\\u000a antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided

Valery M. Dembitsky

2005-01-01

207

Effects of the isoflavone puerarin and its glycosides on melanogenesis in B16 melanocytes  

Microsoft Academic Search

We investigated the effects of puerarin (8-C-glucosyl-7,4?-dihydroxy isoflavone), an isoflavone found in Kudzu roots (Pueraria lobata), and its glycosides (enzymatically synthesised, water-soluble derivatives of puerarin) on melanogenesis in vitro. Puerarin\\u000a and its glycosides reduced mushroom tyrosinase activity by 88 and 67% at 4.8 mM, respectively, in a concentration-dependent\\u000a manner. The puerarin glycosides were less effective than puerarin at the same concentration

Young-Mi Choi; Hee-jin Jun; Kevin Dawson; Raymond L. Rodriguez; Mi Ran Roh; Jungae Jun; Chung-Hyo Choi; Jae-Hoon Shim; ChoongHwan Lee; Sang Jun Lee; Kwan-Hwa Park; Sung-Joon Lee

2010-01-01

208

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

SciTech Connect

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.

Tyler, Ludmila [USDA-ARS Western Regional Research Center; Bragg, Jennifer [USDA-ARS Western Regional Research Center; Wu, Jiajie [USDA-ARS Western Regional Research Center; Yang, Xiaohan [ORNL; Tuskan, Gerald A [ORNL; Vogel, John [USDA-ARS Western Regional Research Center

2010-01-01

209

Changes in histamine secretion from mast cells caused by digitalis glycosides  

Microsoft Academic Search

Cardiotonic glycosides modify histamine secretion from rat mast cells in the following way. (1) Preincubation (30 min) of mast cells with liposoluble glycosides (10?4 mol\\/l) increases the spontaneous histamine secretion by about 5%. (2) Preincubation of mast cells with 10?4 mol\\/l liposoluble glycosides (digitoxine, digoxine, digitoxigenine) decreases histamine release induced by compound 48\\/80 in the presence of calcium, whereas the

F. Erjavec; I. Ferjan

1990-01-01

210

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

PubMed Central

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.

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

2011-01-01

211

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

PubMed

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

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

2012-08-01

212

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

PubMed Central

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.

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

2012-01-01

213

Reverse Logistics.  

National Technical Information Service (NTIS)

The Army has a serious problem with materiel in the supply chain that is moving in the reverse direction. The supply chain is a series of inter- related processes and activities that move supplies and services from the suppliers to the ultimate end users....

J. L. Walden

2001-01-01

214

Reverse traceroute  

Microsoft Academic Search

Traceroute is the most widely used Internet diagnos- tic tool today. Network operators use it to help identify routing failures, poor performance, and router misconfig- urations. Researchers use it to map the Internet, predict performance, geolocate routers, and classify the perfor- mance of ISPs. However, traceroute has a fundamental limitation that affects all these applications: it does not provide reverse

Ethan Katz-Bassett; Harsha V. Madhyastha; Colin Scott

215

Reverse traceroute  

Microsoft Academic Search

Traceroute is the most widely used Internet diagnostic tool today. Network operators use it to help identify routing fail- ures, pathinflation, androutermisconfigurations. Researchers use it to map the Internet, predict performance, geolocate routers, and classify the performance of ISPs. However, traceroute has long had a fundamental limitation that affects all these applications: it does not provide reverse path infor- mation.

Ethan Katz-Bassett; Harsha V. Madhyastha; Vijay Kumar Adhikari; Colin Scott; Justine Sherry; Peter van Wesep; Thomas E. Anderson; Arvind Krishnamurthy

2010-01-01

216

One-pot hydrothermal synthesis of peony-like Ag/Ag(0.68)V2O5 hybrid as high-performance anode and cathode materials for rechargeable lithium batteries.  

PubMed

A peony-like Ag/Ag0.68V2O5 hybrid assembled from nanosheets with the thickness of 40 nm was synthesized through a one-pot hydrothermal approach from vanadium pentoxide (V2O5), oxalic acid (H2C2O4), and silver nitrate (AgNO3) at 180 °C for 24 h. The hybrid exhibits high performance as both anode and cathode materials for rechargeable lithium batteries. Electrochemical measurements revealed that the as-prepared Ag/Ag0.68V2O5 hybrid displayed excellent cycling stability, especially as an anode material. The resulting anode retains 100% of the initial capacity after 1000 cycles under a current density of 400 mA g(-1). This phenomenon may be attributed to electron conductivity improvement by the existence of metallic silver in the hybrid in addition to the convenient access to lithium ion ingress/egress because of its unique structure. PMID:24686721

Wei, Denghu; Li, Xiaona; Zhu, Yongchun; Liang, Jianwen; Zhang, Kailong; Qian, Yitai

2014-05-21

217

Steroidal glycosides from the underground parts of Helleborus caucasicus.  

PubMed

Four polyhydroxylated and polyunsaturated furostanol glycosides (1-4), named caucasicosides A (1), B (2), C (3) and D (4), were isolated from the MeOH extract of the underground parts of Helleborus caucasicus, along with four spirostanol derivatives, a furostanol glycoside, a furospirostanol glycoside, 20-hydroxyecdysone and the bufadienolides hellebrigenin and deglucohellebrin. The structures of 1-4 were elucidated as furosta-5,20(22),25(27)-triene-1beta,3beta,11alpha,26-tetrol 26-O-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1beta,3beta,11alpha,26-tetrol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (2), 26-O-beta-d-glucopyranosyl-22alpha-methoxyfurosta-5,25(27)-diene-1beta,3beta,11alpha,26-tetrol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (3), 26-O-beta-D-glucopyranosylfurosta-5,20(22),25(27)-triene-1beta,3beta,26-triol 3-O-beta-D-xylopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-4-O-sulfo-alpha-L-arabinopyranoside (4). Structure elucidation was accomplished through the extensive use of 1D- and 2D NMR experiments including 1H-1H (COSY, 1D-TOCSY) and 1H-13C (HSQC, HMBC) spectroscopy along with ESI-MS and HR-ESI-MS. The aglycones of 1-4 have never been reported before. PMID:18226823

Bassarello, Carla; Muzashvili, Tamara; Skhirtladze, Alexandre; Kemertelidze, Ether; Pizza, Cosimo; Piacente, Sonia

2008-03-01

218

A new flavonol glycoside from the Abelmoschus esculentus Linn.  

PubMed Central

Background: Abelmoschus esculentus L. belonging to the family Malvaceae is a kind of one year herbage plant, which is one of the most important vegetables widely grown in Nigeria for its tender fruits and young leaves. It's easy to be cultivated and grows well in both tropical and temperate zones, that is, it is widely planted from Africa to Asia, South European to America. A new flavonol glycoside characterized as 5,7,3?,4?-tetrahydroxy-4??-O-methyl flavonol -3-O-?-D- glucopyranoside (1) has been isolated from the fruit of A. esculentus together with one known compound 5,7,3?,4?-tetrahydroxy flavonol -3-O-[?-D-glucopyranosyl-(1?6)]-?-D-glucopyranoside (2). The structure of the new compound was elucidated on the basis of its spectral data, including 2-D NMR and mass (MS) spectra. The antioxidant activities of the isolated compounds 1 and 2 were evaluated by 2 assays, the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and ferric reducing antioxidant power (FRAP). The present work deals with the isolation, identification and antioxidant activity of the two compounds. Materials and Methods: The compounds were isolated by Diaion HP-20, Sephedex LH-20 column chromatography methods, their structures were identified by physicochemical properties and spectroscopic analysis. The antioxidant activities of the isolated compounds 1 and 2 were evaluated by two assays, e.g., DPPH and FRAP. Results: Two flavonol glycosides have been isolated from the fruit of Abelmoschus esculentus L. for the first time, and the compound 1 was a new compound, the compound 2 was isolated from the plant for the first time. Conclusion: The results show that the two flavonol glycosides have strong ability for scavenging DPPH and FRAP free radical by the experiment of antioxidant activities, so A. esculentus may be a natural antioxidants resource.

Liao, Haibing; Liu, Huixin; Yuan, Ke

2012-01-01

219

Steroidal glycosides with antiproliferative activities from Digitalis trojana.  

PubMed

The phytochemical investigation of Digitalis trojana led to the isolation of two cardiac glycosides (1, 2), one pregnane glycoside (3), three furostanol type saponins (4-6), along with three cleroindicins (7-9), four phenylethanoid glycosides (10-13), two flavonoids (14, 15) and two phenolic acid derivatives (16, 17). The structure elucidation of the isolates was carried out by NMR experiments as well as ESI-MS. The cytotoxic activity of compounds 1-13 against a small panel of cancer cell lines, namely MCF-7, T98G, HT-29, PC-3, A375 and SH-SY5Y, was investigated. Compounds 1-6 showed antiproliferative activity against human breast MCF-7 and colon HT-29 cancer cell lines with IC50 values ranging from 8.3 to 50??M. In order to understand the mechanism involved in the cell death, the active compounds were tested as pro-apoptotic agents using propidium iodide staining by flow cytometry method. No significant increase was observed in the apoptosis of the MCF-7 and HT-29 cancer cells. Moreover, the effects of the active compounds on cell proliferation were assessed on the same cancer cell lines by cell cycle analysis of DNA content using flow cytometry. No significative changes were observed in the cell cycle of MCF-7, while significant changes in G2 /M cell cycle phase of HT-29 cells were observed after treatment with digitalin (1), cariensoside (3) and 22-O-methylparvispinoside B (6) at 10??M. PMID:23722601

Kirmizibekmez, Hasan; Masullo, Milena; Festa, Michela; Capasso, Anna; Piacente, Sonia

2014-04-01

220

Reverse Osmosis  

NSDL National Science Digital Library

North Dakota State University presents the theories behind reverse osmosis and how it affects household water supplies. The site addresses the impurities which are removed by this process. It also speaks of testing, the process itself and even the disadvantages of this process. A fairly encompassing site is what amounts from the work done by the University, it gives a clear and concise viewpoint of this process.

2008-10-13

221

Inhibition of amyloid ? aggregation by acteoside, a phenylethanoid glycoside.  

PubMed

We examined the effects of acteoside (1a), which was isolated from Orobanche minor, and its derivatives on the aggregation of a 42-mer amyloid ? protein (A?42) in our search for anti-amyloidogenic compounds for Alzheimer's disease (AD) therapy. Acteoside (1a) strongly inhibited the aggregation of A?42 in a dose-dependent manner. The structure-activity relationship for acteoside (1a) and related compounds suggests the catechol moiety of phenylethanoid glycosides to be essential for this inhibitory activity. PMID:23748773

Kurisu, Manami; Miyamae, Yusaku; Murakami, Kazuma; Han, Junkyu; Isoda, Hiroko; Irie, Kazuhiro; Shigemori, Hideyuki

2013-01-01

222

Four New Flavonol Glycosides from the Leaves of Brugmansia suaveolens.  

PubMed

Four new flavonol glycosides were isolated from the leaves of Brugmansia suaveolens: kaempferol 3-O-?-D-glucopyranosyl-(1'''?2'')-O-?-L-arabinopyranoside (1), kaempferol 3-O-?-D-glucopyranosyl-(1'''?2'')-O-?-L-arabinopyranoside-7-O-?-D-gluco-pyranoside (2), kaempferol 3-O-?-D-[6'''-O-(E-caffeoyl)]-glucopyranosyl-(1'''?2'')-O-?-l-arabinopyranoside-7-O-?-D-glucopyranoside (3), and kaempferol 3-O-?-D-[2'''-O-(E-caffeoyl)]-glucopyranosyl-(1'''?2'')-O-?-l-arabinopyranoside-7-O-?-D-glucopyranoside (4). The structure elucidation was performed by MS, 1D and 2D NMR analyses. PMID:24858103

Geller, Fabiana; Murillo, Renato; Steinhauser, Lisa; Heinzmann, Berta; Albert, Klaus; Merfort, Irmgard; Laufer, Stefan

2014-01-01

223

A new phenolic amide glycoside from Cimicifuga dahurica.  

PubMed

A new phenolic amide glycoside, cimicifugamide A (1) along with four known compounds, trans-feruloyl tyramine 4-O-beta-D-glucopyranoside (2), (+)-isolariciresinol 3-O-beta-D-glucopyranoside (3), cimidahurine (4), and 24-epi-7, 8-didehydrocimigenol-3-O-beta-D-xylopyranoside (5) were isolated from the rhizomes of Cimicifuga dahurica. Compound 3 was identified as a lignan and has been obtained from Cimicifuga genus for the first time. The structure of compound 1 was elucidated by IR, UV, HR-MS and NMR spectroscopic methods. PMID:24187836

Zhang, Fan; Han, Li-Feng; Pan, Gui-Xiang; Peng, Shuang; Andre, Ndagijimana

2013-08-01

224

A new spirostanol glycoside from fruits of Solanum indicum L.  

PubMed

A new characteristic steroidal glycoside of the 23S,26R-hydroxylated spirostanol-type named indioside F was isolated from the fruit of Solanum indicum, along with indioside A and protodioscin. On the basis of spectroscopic analysis, the structure of indioside F was found to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranosyl (beta-chacotriosyl) (22R,23S,25R,26R)-spirost-5-ene-3beta,23,26-triol. PMID:19571425

El-Aasr, Mona; Miyashita, Hiroyuki; Ikeda, Tsuyoshi; Lee, Jong-Hyun; Yoshimitsu, Hitoshi; Nohara, Toshihiro; Murakami, Kotaro

2009-07-01

225

A new hexenol glycoside from leaves of Smallanthus sonchifolius  

Microsoft Academic Search

A new hexenol glycoside with two known compounds was isolated from the leaves of Smallanthus sonchifolius. The structure of the new compound was elucidated as Z-hex-3-en-1-ol O-alpha-L-arabinopyransyl (1??-2?)-beta-D-glucopyranoside (1) on the basis of spectroscopic analysis and chemical evidence. The two known compounds were identified as ent-15?-hydroxy-kaur-16-en-19-oic acid (2) and ent-18-hydroxy-kaur-16-en-19-oic acid (3) by comparison of their spectral data with the

Xiang Zheng; Gai Kuo; Dou De-Qiang; Chen Gui-Rong; Kang Ting-Guo; Shi Yu-Yuan; Li Xing-Tai; Dong Feng

2010-01-01

226

A new cucurbitacin glycoside from Kageneckia oblonga (Rosaceae).  

PubMed

A novel cucurbitacin glycoside has been isolated from aerial parts of Kageneckia oblonga R. et P. and shown to be 3beta-(beta-D-glucosyloxy)-16alpha,23alpha-epoxycuc urbita-5,24-dien-11-one. The structure was established by usual spectroscopic and two-dimensional (2D) NMR techniques. This compound has found to be nontoxic when tested in-vivo cell culture assays. In previous investigations we reported 23,24-dihydrocucurbitacin F and prunasine. This was the first report on cucurbitacins from the genus Kageneckia (Rosaceae). PMID:10817201

Muńoz, O; Delporte, C; Backhouse, N; Erazo, S; Negrete, R; Maldonado, S; López-Pérez, J L; San Feliciano, A

2000-01-01

227

Two new phenolic glycosides from the rhizome of Gastrodia elata  

Microsoft Academic Search

Two new phenolic glycosides, named parishins F–G (1–2), together with known parishin E, were isolated from the rhizome of Gastrodia elata. The new structures were established as 1,3-di-[4-O-(?-d-glucopyranosyl) benzyl]-2-{4-O-[?-d-glucopyranosyl-(1 ? 6)-?-d-glucopyranosyl] benzyl} citrate (1) and 2-[4-O-(?-d-glucopyranosyl)benzyl] citrate (2), by means of MS, 1D, and 2D NMR spectral analyses, as well as chemical methods.

Li Wang; Hong-Bin Xiao; Li Yang; Zheng-Tao Wang

2012-01-01

228

Two new phenolic glycosides from the rhizome of Gastrodia elata.  

PubMed

Two new phenolic glycosides, named parishins F-G (1-2), together with known parishin E, were isolated from the rhizome of Gastrodia elata. The new structures were established as 1,3-di-[4-O-(?-D-glucopyranosyl) benzyl]-2-{4-O-[?-D-glucopyranosyl-(1 ? 6)-?-D-glucopyranosyl] benzyl} citrate (1) and 2-[4-O-(?-D-glucopyranosyl)benzyl] citrate (2), by means of MS, 1D, and 2D NMR spectral analyses, as well as chemical methods. PMID:22428666

Wang, Li; Xiao, Hong-Bin; Yang, Li; Wang, Zheng-Tao

2012-01-01

229

Pentasaccharide resin glycosides from Ipomoea cairica and their cytotoxic activities.  

PubMed

Six partially acylated pentasaccharide resin glycosides, cairicosides A-F, were isolated from the aerial parts of Ipomoea cairica. These compounds were characterized as a group of macrolactones of simonic acid A, partially acylated with different organic acids. The lactonization site of 11S-hydroxyhexadecanoic acid (jalapinolic acid) was bound to the second saccharide moiety at C-3 in cairicosides A-E, while at C-2 in cairicoside F. Structures were established by spectroscopic and chemical methods. Compounds cairicosides A-E exhibited moderate cytotoxicity against a small panel of human tumor cell lines with IC50 values in the range of 4.28-14.31?M. PMID:23954073

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

2013-11-01

230

Reverse convection  

SciTech Connect

A model of magnetospheric topology for periods when the interplanetary magnetic field (IMF) points northward indicates that reverse convection can readily occur when Earth's dipole or the IMF tilt toward or away from the Sun. In either case, all or part of one tail lobe drapes over the dayside, and the magnetopause merging voltage is applied directly to the ionosphere in that lobe only, to the center or nightside of the polar cap. The overdraped lobe forms layers both earthward and sunward of the magnetopause, similar to layers observed during periods of northward IMF. The model predicts two quasi-steady state patterns of reverse convection: (1) lobe cells in the polar cap of the overdraped lobe, generated by open-to-open flux transfer at the magnetopause and (2) merging cells in both polar caps, generated by closed-to-open flux transfer at the magnetopause and balanced open-to-closed transfer at an internal reconnection site, comparable to the tail merging site for southward IMF. The model also predicts transitional patterns of reverse convection for growing and shrinking polar caps in response to changes in dipole tilt and B[sub x] and in response to a sudden transition from southward to northward IMF. The model predicts theta aurora bar formation on the dawnside polar cap boundary when activation of the internal reconnection site ends polar cap growth. In this view the theta aurora becomes the northward IMF counterpart to substorms.

Crooker, N.U. (Univ. of California, Los Angeles (United States))

1992-12-01

231

Morning glory resin glycosides as modulators of antibiotic activity in multidrug-resistant gram-negative bacteria.  

PubMed

Twenty-six microbiologically inactive (MIC >?512?µg/mL) convolvulaceous resin glycosides ( 1- 26) were tested for resistance modulatory activity in vitro against Escherichia coli Rosetta-gami and two nosocomial pathogens, Salmonella typhi and Shigella flexneri. These compounds exerted a potentiation effect of the clinically useful antibiotics tetracycline, kanamycin, and chloramphenicol against the tested gram-negative bacteria by increasing antibiotic susceptibility up to 32-fold at concentrations of 25?µg/mL. Therefore, the oligosaccharides from the morning glory family (Convolvulaceae) represent metabolites that reverse microbial resistance mechanisms, favoring an increase in the strength and effectiveness of current antibiotics that are not effective in the treatment of refractive infections caused by multidrug-resistant strains. PMID:22002849

Corona-Castańeda, Berenice; Pereda-Miranda, Rogelio

2012-01-01

232

Antioxidative activity of the crude extract of lignan glycosides from unroasted Burma black sesame meal  

Microsoft Academic Search

Sesame seed contains lignans and lignan glycosides. The antioxidative activity of the crude extract of lignan glycosides obtained from unroasted defatted black sesame seeds was investigated in this study. The components responsible for the antioxidative activity were also studied. The unroasted black sesame seeds, after defatted with n-hexane, were extracted with 80% methanolic solution to prepare for the crude extract

Yung-Shin Shyu; Lucy Sun Hwang

2002-01-01

233

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

PubMed

Two new 27-nor-triterpene glycosides, tomentosides A (1) and B (2), were isolated from Peruvian "Uńa de Gato" (cat's claw, plant of origin: Uncaria tomentosa), a traditional herbal medicine in Peru. Their structures were determined by spectroscopic analysis and chemical interconversions. This is the first report of naturally occurring pyroquinovic acid glycosides. PMID:12608878

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

2003-02-01

234

Morphological basis of cardiac glycoside sequestration by Oncopeltus fasciatus (Dallas) (Hemiptera: Lygaeidae)  

Microsoft Academic Search

The integument of Oncopeltus fasciatus is made up of a vacuolated and a pigmented epidermal cell layer. This double layered integument is present from late embryo to adult in male and female animals reared on milkweed or sunflower seeds. Experiments with a labelled glycoside as well as retrograde ink injections suggest that O. fasciatus concentrates cardiac glycosides, normally derived from

G. G. E. Scudder; J. Meredith

1982-01-01

235

Determining levels of steviol glycosides in the leaves of Stevia rebaudiana by near infrared reflectance spectroscopy  

Microsoft Academic Search

The sweet diterpene glycosides extracted from the leaves of Stevia rebaudiana (Bert) Bertoni are of increasing interest in recent years as possible sugar substitutes. Our objectives were to investigate the application of near infrared reflectance spectroscopy (NIRS) in analysis of steviol glycosides (SGs) concentration (w\\/w) dry basis in S. rebaudiana leaves, using high-pressure liquid chromatography (HPLC) as the reference method.

L. K. Hearn; P. P. Subedi

2009-01-01

236

Molecular basis for fungicidal action of neothyonidioside, a triterpene glycoside from the sea cucumber, Australostichopus mollis.  

PubMed

Neothyonidioside is a triterpene glycoside (TG) isolated from the sea cucumber, Australostichopus mollis, that is potently cytotoxic to S. cerevisiae, but does not permeabilize cellular membranes. We mutagenized S. cerevisiae and isolated a neothionidioside-resistant (neo(R)) strain. Using synthetic genetic array mapping and sequencing, we identified NCP1 as the resistance locus. Quantitative HPLC revealed that neo(R)/ncp1 mutants have reduced ergosterol content. Ergosterol added to growth media reversed toxicity, demonstrating that neothionidioside binds directly to ergosterol, similar to the polyene natamycin. Ergosterol synthesis inhibitors ketoconazole and atorvastatin conferred resistance to neothionidioside in a dose-dependent manner showing that a threshold ergosterol concentration is required for toxicity. A genome-wide screen of deletion mutants against neothionidioside revealed hypersensitivity of many of the component genes in the ESCRT complexes relating to multivesicular body formation. Confocal microscopy of cells stained with a vital dye showed blockage at this step. Thus, we propose neothionidioside may affect membrane curvature and fusion capability in the endosome-vacuole pathway. PMID:22271309

Yibmantasiri, Ploi; Leahy, Dora C; Busby, Bede P; Angermayr, Stephan Andreas; Sorgo, Alice G; Boeger, Kristina; Heathcott, Rosemary; Barber, Jacqueline M; Moraes, Greta; Matthews, James H; Northcote, Peter T; Atkinson, Paul H; Bellows, David S

2012-03-01

237

Extracellular versus intracellular digoxin action on bovine myocardium, using a digoxin antibody and intracellular glycoside application.  

PubMed Central

1. The actions of externally and internally applied digoxin in heart ventricular muscle have been compared. 2. External application of digoxin (5 x 10(-8)--10(-7) M) had an inotropic effect, a steady level of twitch tension being reached at the end of about 3 hr. 3. Addition of an anti-digoxin antibody to the bathing solution prevented or reversed the digoxin effect, depending on the time of application. 4. The efflux of the antibody-[3H]digoxin-complex could be fitted by a single exponential with a half-time of 18 min. 5. In the absence of antibody, [3H]digoxin washout was two-compartmental with half-times of 4 and 72 min respectively. It is thought that the fast process signifies efflux from the extracellular space while the slow process reflects the washout of initially membrane bound glycoside. 6. When digoxin was applied by a cut end method, there was no effect on contractile strength. 7. The profile of radioactivity several hours following exposure to [3H]digoxin clearly indicated movement from cell to cell, the concentration of [3H]digoxin being above 10(-7) M in half the preparation at the end of 6 hr. Longitudinal diffusivity averaged 8.6 x 10(-8) cm-2 sec-1. 8. We conclude that digoxin has an inotropic effect when reaching the surface membrane of cardiac cells from the outside but is ineffective when applied from the inside.

Hess, P; Muller, P

1982-01-01

238

Target-specific imaging of transmembrane receptors using quinonyl glycosides functionalized quantum dots.  

PubMed

Here, we describe a novel "switch-on" biosensor based on quinonyl glycosides functionalized quantum dots (QDs) for the specific targeting and imaging of transmembrane glycoprotein receptors on the surface of cancer cells. The design of the quinonyl glycosides lies in that the quinone moiety serves as a quencher of QDs and the glycoside moiety as a biospecific ligand for targeting a receptor. We observed that the quenched photoluminescence of the quinone glycosides functionalized QDs could be significantly recovered by a specific lectin that selectively binds to the glycosides clustering the QDs but was not affected by a panel of nonspecific lectins. Moreover, we determined that quinonyl galactoside functionalized QDs could optically image the asialoglycoprotein receptors of a hepatoma cell line in a target-specific manner. This system might provide new insights into the fabrication of photoluminogenic biosensors for the analysis of the universal ligand-receptor recognitions in nature. PMID:24803208

Ma, Wei; Liu, Hui-Ting; He, Xiao-Peng; Zang, Yi; Li, Jia; Chen, Guo-Rong; Tian, He; Long, Yi-Tao

2014-06-01

239

Stepwise synthesis of a GalNAc-containing cluster glycoside ligand of the asialoglycoprotein receptor.  

PubMed

A series of peptidylglycoside derivatives, including the tris(GalNAc-aminohexyl) glycoside of tyrosyl(glutamyl)-glutamate (1) which is known to have sub-nanomolar affinity for the asialoglycoprotein receptor (ASGPr), have been synthesized using the protected tetra-O-acetyl aminohexyl glycoside (9) of N-acetylgalactosamine. The N-succinyl derivative of 1 was also prepared, providing a derivative for bioconjugate formation via carboxyl activation of the glycopeptide. Use of the protected glycoside 9 affords synthetic intermediates with increased solubility in organic solvents that are easier to purify and use in subsequent synthetic manipulations in comparison with compounds containing unprotected glycosides. These synthetic procedures will be generally applicable to the preparation of related compounds to probe binding to the ASGPr and the use of these cluster glycosides as ligands for targeted delivery to the liver. PMID:8070972

Findeis, M A

1994-05-01

240

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

PubMed

Meeting the rising consumer demand for natural food ingredients, steviol glycosides, the sweet principle of Stevia rebaudiana Bertoni (Bertoni), have recently been approved as food additives in the European Union. As regulatory constraints require sensitive methods to analyze the sweet-tasting steviol glycosides in foods and beverages, a HILIC-MS/MS method was developed enabling the accurate and reliable quantitation of the major steviol glycosides stevioside, rebaudiosides A-F, steviolbioside, rubusoside, and dulcoside A by using the corresponding deuterated 16,17-dihydrosteviol glycosides as suitable internal standards. This quantitation not only enables the analysis of the individual steviol glycosides in foods and beverages but also can support the optimization of breeding and postharvest downstream processing of Stevia plants to produce preferentially sweet and least bitter tasting Stevia extracts. PMID:24206531

Well, Caroline; Frank, Oliver; Hofmann, Thomas

2013-11-27

241

Flavonol glycosides in wild and cultivated berries of three major subspecies of Hippophaë rhamnoides and changes during harvesting period  

Microsoft Academic Search

Flavonol glycosides are an important group of bioactive components of sea buckthorn (Hippophaë rhamnoides). The content and profile of flavonol glycosides of some major subspecies and most cultivars as well as the variation amongst the harvesting years and dates are largely unknown. This study investigated flavonol glycosides in wild berries of two major subspecies H. rhamnoides ssp. rhamnoides and ssp.

Baoru Yang; Teemu Halttunen; Olli Raimo; Keith Price; Heikki Kallio

2009-01-01

242

Micromolar concentrations of EGTA increase histamine secretion from mast cells treated with digitalis glycosides of different polarity  

Microsoft Academic Search

Histamine release from rat peritoneal mast cells induced by compound 48\\/80 (1 ?g\\/ml) after 90 min of preincubation in calcium — free medium is only 8.4%. Cardiotonic glycosides modify the secretion induced by compound 48\\/80: hydrophlic glycosides potentiate the secretion, and this potentiation decreases with increasing lipophility of the glycosides.

Ilonka Ferjan; F. Erjavec

1993-01-01

243

Identification of a novel flavonoid glycoside sulfotransferase in Arabidopsis thaliana.  

PubMed

The discovery of sulfated flavonoids in plants suggests that sulfation may play a regulatory role in the physiological functions of flavonoids. Sulfation of flavonoids is mediated by cytosolic sulfotransferases (SULTs), which utilize 3'-phosphoadenosine 5'-phosphosulfate (PAPS) as the sulfate donor. A novel SULT from Arabidopsis thaliana, designated AtSULT202B7 (AGI code: At1g13420), was cloned and expressed in Escherichia coli. Using various compounds as potential substrates, we demonstrated, for the first time, that AtSULT202B7 displayed sulfating activity specific for flavonoids. Intriguingly, the recombinant enzyme preferred flavonoid glycosides (e.g. kaempferol-3-glucoside and quercetin-3-glucoside) rather than their aglycone counterparts. Among a series of hydroxyflavones tested, AtSULT202B7 showed the enzymatic activity only for 7-hydroxyflavone. pH-dependency study showed that the optimum pH was relatively low (pH 5.5) compared with those (pH 6.0-8.5) previously reported for other isoforms. Based on the comparison of high performance (pressure) liquid chromatography (HPLC) retention times between sulfated kaempferol and the deglycosylated product of sulfated kaempferol-3-glucoside, the sulfation site in sulfated kaempferol-3-glucoside appeared to be the hydroxyl group of the flavonoid skeleton. In addition, by using direct infusion mass spectrometry, it was found that the sulfated product had one sulfonate group within the molecule. These results indicated that AtSULT202B7 functions as a flavonoid glycoside 7-sulfotransferase. PMID:24202284

Hashiguchi, Takuyu; Sakakibara, Yoichi; Shimohira, Takehiko; Kurogi, Katsuhisa; Yamasaki, Masao; Nishiyama, Kazuo; Akashi, Ryo; Liu, Ming-Cheh; Suiko, Masahito

2014-02-01

244

Cytotoxic cardiac glycosides from the roots of Streptocaulon juventas.  

PubMed

Chemical investigation on the 75% ethanol extract of the roots of Streptocaulon juventas afforded two new cardiac glycosides, digitoxigenin 3-O-[O-?-D-glucopyranosyl-(1 ? 4)-2-O-acetyl-?-D-digitalopyranoside] (1) and periplogenin 3-O-[O-?-D-glucopyranosyl-(1 ? 4)-O-?-D-glucopyranosyl-(1 ? 4)-?-D-cymaropyranoside] (2), and thirteen known cardenolides. Structures were elucidated by spectral methods. This is the first report of the isolation of compounds 3, 10, 14, and 15 from plants of the Streptocaulon genus, while 4, 11, and 12 are hitherto unreported from Streptocaulon juventas. All the compounds were in vitro evaluated for their cytotoxic activities against the A549 cell line, and seven effective cardiac glycosides were screened against the PC-9 cell line by WST assay, which also showed strong antiproliferation activities. Moreover, the characteristic morphological changes in PC-9 cells treated with cardenolides indicated cell inhibition due to apoptosis. These results revealed that these compounds possessed potential antitumor activities. PMID:23225367

Xue, Rui; Han, Na; Sakurai, Hiroaki; Saiki, Ikuo; Ye, Chun; Yin, Jun

2013-01-01

245

Recovering glycoside hydrolase genes from active tundra cellulolytic bacteria.  

PubMed

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

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

2014-07-01

246

Allosteric indicator displacement enzyme assay for a cyanogenic glycoside.  

PubMed

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 ?-glucosidase and a boronic acid appended viologen together with a fluorescent reporter dye. ?-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 ?-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

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

2013-10-18

247

Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.  

PubMed

Eight new cardiac glycosides/aglycones (antiaritoxiosides A-G, 1-7, and antiarotoxinin B, 8), two new coumarins (anticarins A-B, 41-42), and two new flavanones (antiarones L-K, 43-44) were isolated from trunk bark of Antiaris toxicaria together with 53 known compounds. The new structures were established by extensive analysis of spectroscopic data. Compound 1 (10-carboxy and 3?-hydroxy) and compounds 3-6 (10-hydroxy) contain unique substituents that are rarely found in cardiac glycosides. The cytotoxic effects of isolated compounds against ten human cancer cell lines, KB, KB-VIN, A549, MCF-7, U-87-MG, PC-3, 1A9, CAKI-1, HCT-9 and S-KMEL-2, were tested using the sulforhodamine B assay. Five compounds (12, 16, 20, 22, and 31) showed significant cytotoxicity against all ten cancer cell lines, with notable potency at the ng/mL level against some cell lines, which merits further development as clinical trial candidates. PMID:24582402

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

2014-03-15

248

Angling for Uniqueness in Enzymatic Preparation of Glycosides  

PubMed Central

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 bird’s-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.

Trincone, Antonio

2013-01-01

249

Oleanane-type glycosides from Tremastelma palaestinum (L.) Janchen.  

PubMed

Three new oleanane-type glycosides, 1-3, were isolated from the whole plant of Tremastelma palaestinum (L.) Janchen, along with eight known triterpene glycosides. The structures of the new compounds were established as 3-O-[?-d-glucopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?3)-?-d-glucopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-l-arabinopyranosyl]hederagenin (1), 3-O-[?-d-glucopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?3)-?-d-glucopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-l-arabinopyranosyl]hederagenin 28-O-?-d-glucopyranosyl-(1?6)-?-d-glucopyranosyl ester (2), and 3-O-[?-l-rhamnopyranosyl-(1?3)-?-d-glucopyranosyl-(1?3)-?-l-rhamnopyranosyl-(1?2)-?-l-arabinopyranosyl]oleanolic acid 28-O-?-d-glucopyranosyl-(1?6)-?-d-glucopyranosyl ester (3) by using 1D- and 2D-NMR techniques and mass spectrometry. This is the first report on the phytochemical investigation of a species belonging to Tremastelma genus. PMID:24634070

?enel, Gökhan; Gülcemal, Derya; Masullo, Milena; Piacente, Sonia; Karay?ld?r?m, Tamer

2014-03-01

250

Oleanane type glycosides from Paronychia anatolica subsp. balansae.  

PubMed

Four new oleanane-type triterpene glycosides were isolated from the methanol extract of the roots of Paronychia anatolica subsp. balansae along with three known oleanane-type triterpene glycosides. Structures of the new compounds were established as 3-O-?-D-glucuronopyranosyl-28-O-[?-L-rhamnopyranosyl-(1?2)-?-D-quinovopyranoside] zahnic acid, 3-O-?-D-glucuronopyranosyl-28-O-[?-D-xylopyranosyl-(1?4)-?-L-rhamnopyranosyl-(1?2)-?-D-quinovopyranoside] zahnic acid, 3-O-?-D-glucuronopyranosyl-28-O-[?-L-arabinofuranosyl-(1?2)-?-D-quinovopyranoside] zahnic acid, 28-O-[?-L-rhamnopyranosyl-(1?4)-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl]-medicagenic acid, by using 1D and 2D-NMR techniques and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including human breast cancer (MCF-7), human lung adenocarcinoma (A549) and human leukemia (U937) cell lines. PMID:24321579

Gülcemal, Derya; Masullo, Milena; Alanku?-Çal??kan, Özgen; Piacente, Sonia

2014-01-01

251

Glycosidated phospholipids - a promising group of anti-tumour lipids.  

PubMed

Synthetic alkylphospholipids (APLs), exhibit similarity to the platelet-activating factor (PAF). These compounds have antiproliferative effects on tumour cells and can therefore be regarded as a new class of drugs. Unlike classic cytostatic agents, synthetic alkylphospholipids do not interfere with the DNA or the mitotic spindle apparatus. Instead, due to their aliphatic character, alkylphospholipids accumulate in cell membranes, where they have an impact on lipid metabolism and lipid-dependent signalling pathways which leads to inhibition of proliferation and induction of apoptosis in malignant cells. Normal cells remain unaffected by these compounds. Glycosidated phospholipids, are a novel class of alkylphospholipids, in which carbohydrates or carbohydrate-related molecules are introduced in the chemical lead of PAF. These hybrid alkylphospholipids also exhibit anti-proliferative capacity. Furthermore, members of this subfamily also modulate cell adhesion, differentiation, apoptosis and migration of tumour cells. Among the members of this group, Inositol-C2-platelet-activating factor (Ino-C2-PAF) is the most effective compound developed so far. Recently, we also showed that Ino-C2-PAF exhibited the strongest impact on the gene expression levels of immortalised keratinocytes in comparison to edelfosine and another glycosidated alkylphospholipid, Glucose-platelet-activating factor (Glc-PAF). Furthermore, Ino-C2-PAF reduced the expression of genes encoding proteins associated with inflammation and the innate and acquired immune responses. PMID:24628240

Semini, Geo; Hildmann, Annette; von Haefen, Clarissa; Danker, Kerstin

2014-05-01

252

Steviol glycosides modulate glucose transport in different cell types.  

PubMed

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

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

2013-01-01

253

Steviol Glycosides Modulate Glucose Transport in Different Cell Types  

PubMed Central

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.

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

2013-01-01

254

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

PubMed Central

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.

2013-01-01

255

Microscopic evaluation and seasonal variations of anthraquinone glycosides of cultivated Cassia fistula Linn.  

PubMed

In this report, we present the results of the microscopy, seasonal variations and spectrophotometric estimation of hydroxy-anthraquinone glycosides of culitivated Cassia fistula Linn. The total glycoside contents ofthe morphological parts of this species at different stages of growth are also presented. The study shows that anthraquinone glycosides are concentrated in the leaves (1.75%) and flowers (1.58%) at peak flowering. Notable seasonal variations were observed in the cultivated species. Hydroxyanthraquinones reached peak levels druing the months of September (1.08%) and October (2.20%). There was a significant drop (P < 0.05) in glycoside content during most part of the rainy season. It has been established that anthraquinone glycosides, rather than the aglycones, are the active forms and hence an estimation of the total glycoside content of a sample is a reliable indication of biological activity. The advantages of using the natural anthraquinone laxative when the glycoside content is highest are discussed. The study has provided useful information on the best period for harvesting the morphological parts of C. fistula for drug development. PMID:14510141

Abo, K A; Adeyemi, A A; Sobowale, A O

2001-01-01

256

Reversible Computation and Reversible Programming Languages  

Microsoft Academic Search

A reversible programming language supports deterministic forward and backward computation. This tutorial focuses on a high-level reversible programming language Janus. In common with other programming paradigms, reversible programming has its own programming methodology. Janus is simple, yet powerful, and its constructs can serve as a model for designing reversible languages in general.

Tetsuo Yokoyama

2010-01-01

257

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

PubMed Central

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

Guleria, Praveen; Yadav, Sudesh Kumar

2013-01-01

258

Novel flavonoid glycosides from the bulbs of Urginea indica Kunth.  

PubMed

Three novel flavonoid glycosides, 5,6-dimethyoxy-3',4''-dioxymethylene-7-O-(6''-beta-D-glucopyranosyl-beta-D-glucopyranosyl) flavanone (1), 5,4'-dihydroxy-3-O-alpha-L-rhamnopyranosyl-6-C-glucopyranosyl-7-O-(6''-para-coumaroyl-beta-D-glucopyranosyl) flavone (2) and 5,4'-dihydroxy-3-O-(2'''''-beta-glucopyranosyl-alpha-L-rhamnopyranosyl)-6-C-glucopyranosyl-7-O-(6''-para-coumaroyl-beta-D-glucopyranosyl) flavone (3) were isolated from the 1-butanol soluble fraction of the bulbs of the plant Urginea indica (Indian squill). The structures of the compounds were elucidated on the basis of spectral analysis, including homo- and heteronuclear correlation NMR experiments (COSY, NOESY, HSQC and HMBC) and mass spectra. PMID:20552524

Sultana, Nasim; Akter, Kaisarun; Nahar, Nilufar; Khan, M Shahinul Hoque; Mosihuzzaman, M; Sohrab, Md Hossain; Krohn, Karsten

2010-07-01

259

Three new sesquiterpene glycosides from Dendrobium nobile with immunomodulatory activity.  

PubMed

Dendroside A (1) and dendronobilosides A and B (2 and 3), three new sesquiterpene glycosides, have been isolated from the stems of Dendrobium nobile, a plant used in Chinese traditional medicine. Their structures and stereochemistry were determined as 10beta,12,14-trihydroxyalloaromadendrane 14-O-beta-D-glucopyranoside (1), 10,12-dihydroxypicrotoxane 10,12-di-O-beta-D-glucopyranoside (2), and 6alpha,10,12-trihydroxypicrotoxane 10-O-beta-D-glucopyranoside (3), respectively, on the basis of spectroscopic and chemical methods. Quantum chemistry calculations were used in support of the structural determination of 1. Compounds 1 and 2 were found to stimulate the proliferation of murine T and B lymphocytes in vitro, while compound 3 showed inhibitory activity in this same assay. PMID:11575955

Zhao, W; Ye, Q; Tan, X; Jiang, H; Li, X; Chen, K; Kinghorn, A D

2001-09-01

260

A minor, sweet cucurbitane glycoside from Siraitia grosvenorii.  

PubMed

A minor, sweet cucurbitane-glycoside, named iso-mogroside V (1), was isolated from Luo Han Guo (Siraitia grosvenorii (Swingle) C. Jeffery) along with five previously reported mogrosides. The structure of iso-mogroside V, 3-[(4-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-mogrol-24-O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->6)]beta-D-glucopyranoside, was established on the basis of extensive 2D-NMR (COSY, TOCSY, NOESY, HSQC, and HMBC) and LCMS analyses. The five known mogrosides were identified as mogroside V (2), 11-oxo-mogroside V (3), siamenoside I (4), mogrosides IVa (5) and IVe (6). Iso-mogroside V was determined to be approximately 500 times sweeter than 0.5% (w/v) sucrose. PMID:19634319

Jia, Zhonghua; Yang, Xiaogen

2009-06-01

261

A new flavonol glycoside from the medicinal halophyte Suaeda fruticosa.  

PubMed

A new flavonol glycoside, namely 3-(?-rhamnopyranosyl-(1 ? 2)-[?-xylopyranosyl-(1 ? 6)]-?-glucopyranosyloxy) isorhamnetin was reported from methanol extracts of aerial parts of Suaeda fruticosa for the first time. In this work, liquid chromatography coupled to atmospheric pressure chemical ionisation mass spectrometry, high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy were used to identify this new compound. Structure was elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC and (1)H-(1)H COSY. Antioxidant potentialities of a pure compound were evaluated. The estimation of antioxidant capacities using oxygen radical absorbance capacity (ORAC method) and a cell based-assay (WS1) indicated that this new flavonol exhibited the highest antioxidant activities with an ORAC value of 5.0 ± 0.3 ?mol Trolox/?mol and inhibited the tBH-induced oxidation of 2',7'-dichlorofluorescin with an IC50 value of 4.9 ± 0.6 ?M. PMID:24945315

Oueslati, Samia; Ksouri, Riadh; Pichette, André; Lavoie, Serge; Girard-Lalancette, Karl; Mshvildadze, Vakhtang; Abdelly, Chedly; Legault, Jean

2014-07-01

262

Two new glycosides from the fruits of Forsythia suspense.  

PubMed

Two new glycosides suspensaside C (1) and 2,3,5,6-tetrahydro-jacaranone-4-O-?-D-glucopyranoside (2), together with four known compounds suspensaside A (3), rengynic acid-1'-O-?-D-glucopyranoside (4), forsythoside A (5), and rengynic acid (6), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HR-ESI-MS. All isolates were tested for their cytotoxicities against five human cancer cell lines (A549, Colo-205, Hep-3B, HL60, and KB). Compound 3 exhibited cytotoxicity against HL-60, Hep-3B, and A549 cancer cell lines. PMID:24506327

Yan, Xin-Jia; Bai, Xin-Yu; Liu, Qing-Bo; Liu, Shen; Gao, Pin-Yi; Li, Ling-Zhi; Song, Shao-Jiang

2014-01-01

263

Triterpenoid saponins and monoterpenoid glycosides from Incarvillea delavayi  

Microsoft Academic Search

Two new triterpenoid saponins, incarvillosides A (1) and B (2), and two new monoterpenoid glycosides, incarvillosides C (3) and D (4), were isolated from the high-polarity fraction of the whole plant of Incarvillea delavayi. By means of spectroscopic data and chemical degradation, the structures were established as (3?,21?)-3,19,21,23-tetrahydroxyurs-12-en-28-oic acid 28-O-?-d-glucopyranoside (1), (2?,3?,19?)-2,3,19,23-tetrahydroxyolean-12-en-28-oic acid 28-O-?-d-glucopyranoside (2), (2S,6R)-2,6-dimethyl-1,8-octanediol 1-O-?-d-glucopyranoside (3), and (2S,6R)-2,6-dimethyl-1,8-octanediol

Xin Ge; De-Chang Lin; Wei-Dong Zhang; Xin-Rong Zhang

2009-01-01

264

Enzymatic hydrolysis of steryl glycosides for their analysis in foods.  

PubMed

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 ?(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

Münger, Linda H; Nyström, Laura

2014-11-15

265

Additional minor diterpene glycosides from Stevia rebaudiana Bertoni.  

PubMed

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

Prakash, Indra; Chaturvedula, Venkata Sai Prakash

2013-01-01

266

Acylated flavonol glycosides from the flower of Elaeagnus angustifolia L.  

PubMed

Seven acylated flavonol glycosides named elaeagnosides A-G, in addition to seven known flavonoids were isolated from the flowers of Elaeagnus angustifolia. Their structures were elucidated by different spectroscopic methods including 1D, 2D NMR experiments and HR-ESI-MS analysis. In order to identify natural antioxidant and tyrosinase inhibitor agents, the abilities of these flavonoids to scavenge the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and to inhibit tyrosinase activity were evaluated. Results revealed that two of these compounds had significant anti-oxidant effect and one compound showed weak tyrosinase-inhibitory activity compared with kojic acid, quercetin, or ascorbic acid, which were used as positive control. PMID:24746259

Bendaikha, Sarah; Gadaut, Méredith; Harakat, Dominique; Magid, Alabdul

2014-07-01

267

Iridoid and phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. and their ?-Glucosidase inhibitory activities.  

PubMed

A new phenylpropanoid glycoside, designated Scrophuside (1) and two new iridoid glycosides, respectively named Ningposide I (2) and Ningposide II (3), along with twelve known (4-15) iridoid and phenylpropanoid glycosides were obtained from the roots of Scrophularia ningpoensis Hemsl. by various chromatographic techniques and their structures were established through chemical methods and spectroscopic analyses. Most of the obtained compounds have been screened for ?-Glucosidase inhibitory activity, in which compounds 4, 5, 7, 11, 12, 13, and 14 show significant activity. PMID:24321577

Hua, Jing; Qi, Jin; Yu, Bo-Yang

2014-03-01

268

Estimation of aroma glycosides of nutmeg and their changes during radiation processing  

Microsoft Academic Search

Glycosidically bound volatile compounds of nutmeg were identified as glyco-conjugates of p-cymene-7-ol, eugenol, methoxyeugenol and ?-terpineol. Using phenyl-?-glucoside as external standard the contents of these glycosidic precursors were estimated based on the measurement of TLC spot density on a densitometer. p-Cymene-7-ol rutinoside was the major aroma glycoside (3.15mg\\/100g), followed by glucosides of methoxyeugenol (0.61mg\\/100g), eugenol (0.50mg\\/100g) and ?-terpineol (0.51mg\\/100g). A

Arul Ananthakumar; Prasad S. Variyar; Arun Sharma

2006-01-01

269

Ornithosaponins A-D, four new polyoxygenated steroidal glycosides from the bulbs of Ornithogalumthyrsoides.  

PubMed

By analyzing the steroidal glycoside content of fresh bulbs of Ornithogalum thyrsoides (Liliaceae), we were able to isolate four new polyoxygenated steroidal glycosides, which we named ornithosaponins A-D (1-4). The structures of 1-4 were elucidated on the basis of extensive spectroscopic analysis, including that of 2D NMR data, and the results of acidic or alkaline hydrolysis. The aglycone structure of 1-4 has not been previously reported. It is also notable that ornithosaponins B-D (2-4) have been found to contain 6-deoxy-beta-D-gulopyranose as a sugar component, which is rarely encountered in plant glycosides. PMID:16303157

Kuroda, Minpei; Ori, Kazutomo; Mimaki, Yoshihiro

2006-03-01

270

Suspected cardiac glycoside intoxication in sheep and goats in Namibia due to Ornithogalum nanodes (Leighton).  

PubMed

The main clinical and necropsy features of field and experimental cases of suspected cardiac glycoside intoxication following ingestion and dosing of the plant Ornithogalum nanodes, are described. The distribution of intoxication in the area as well as a description of the plant are given. Plant samples tested for cardiac glycosides by fluorescence polarization immuno-assay (FPIA) gave a strong positive reaction. This is a new finding, as other toxic Ornithogalum species in southern Africa are devoid of cardiac glycoside activity and poisoning with them result only in a severe, often fatal diarrhoea, without obvious cardiac involvement. It is also the first record of toxicity of this particular plant. PMID:9629587

Bamhare, C

1998-03-01

271

Components of ether-insoluble resin glycoside (convolvulin) from seeds of Quamoclit pennata.  

PubMed

Alkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction of the seeds of Quamoclit pennata BOJER (Convolvulaceae) provided five new glycosidic acids, quamoclinic acids B, C, D, E, and F, along with six organic acids, isobutyric, 2S-methylbutyric, tiglic, 2R,3R-nilic, 7S-hydroxydecanoic, and 7S-hydroxydodecanoic acids. These new compounds were characterized on the basis of spectroscopic data as well as chemical evidence. Quamoclinic acids E and F are the first examples of heptaglycosides of glycosidic acid. PMID:20460794

Ono, Masateru; Takagi-Taki, Yoko; Honda-Yamada, Fumiko; Noda, Naoki; Miyahara, Kazumoto

2010-05-01

272

Na+,K(+)-ATPase inhibiting activity of cardiac glycosides from Erysimum cheiranthoides.  

PubMed

We previously reported the isolation of eleven new cardiac glycosides called cheiranthosides I-XI together with two known ones (olitoriside and erysimoside) from the seeds of Erysimum cheiranthoides L. The glycosides were evaluated for their inhibitory activity against Na+,K(+)-ATPase by comparing with typical cardiac glycosides. Two of them, cheiranthoside III and VIII, showed high inhibiting activity which was equivalent to that of digitoxin. Cheiranthoside XI containing a rhamnopyranosyl digitoxopyranosyl moiety and a carboxyl group showed the lowest activity which was similar to that of the inactive aglycone, strophanthidin. Some characteristics in the structure-activity relationship are also discussed. PMID:11458460

Lei, Z H; Kuniyasu, A; Tai, B S; Nakayama, H; Nohara, T

2001-06-01

273

Chiroptical Properties of Chitin, Chitosan, and Glycosides of N-Acetylglucosamine.  

National Technical Information Service (NTIS)

This report is a compilation of the following articles and patents: Helical Shells and Chiralty; Optically Active Chitosan Solution; Chitin Preparation with Sulfurous Acid; Glucosamine Products for Diet Supplementation; Preparation of Alkyl Glycosides of ...

P. R. Austin C. J. Brine S. N. Hirwe G. A. Reed H. A. Whelan

1980-01-01

274

High-throughput cloning, expression and purification of glycoside hydrolases using Ligation-Independent Cloning (LIC).  

PubMed

Recent advances in DNA sequencing techniques have led to an explosion in the amount of available genome sequencing data and this provided an inexhaustible source of uncharacterized glycoside hydrolases (GH) to be studied both structurally and enzymatically. Ligation-Independent Cloning (LIC), an interesting alternative to traditional, restriction enzyme-based cloning, and commercial recombinatorial cloning, was adopted and optimized successfully for a high throughput cloning, expression and purification pipeline. Using this platform, 130 genes encoding mainly uncharacterized glycoside hydrolases from 13 different organisms were cloned and submitted to a semi-automated protein expression and solubility screening in Escherichia coli, resulting in 73 soluble targets. The high throughput approach proved to be a powerful tool for production of recombinant glycoside hydrolases for further structural and biochemical characterization and confirmed that thioredoxin fusion tag (TRX) is a better choice to increase solubility of recombinant glycoside hydrolases expressed in E. coli, when compared to His-tag alone. PMID:24680731

Camilo, Cesar M; Polikarpov, Igor

2014-07-01

275

Fast atom bombardment and tandem mass spectrometry for structure determination of steroid and flavonoid glycosides.  

PubMed

The combination of fast atom bombardment (FAB) and tandem mass spectrometry (MS-MS) was tested for its applicability to generate useful structural information for steroid and flavonoid glycosides. The following compounds were investigated: quercetin, myricitrin, apigetrin, fraxin, rutin, neohesperidin, hesperidin, naringin, apiin, cymarin, digoxin, digitoxin, xanthorhamnin, and frangulin. Upon FAB, the sample molecules are desorbed as (M + H)+, (M - H)-, or as (M + Na)+ or (M + K)+. Collisional activation of (M + H)+ or (M - H)- ions in the MS-MS experiment leads to sequential losses of glycoside moieties in a manner which permits the sequence of glycosides to be established. Some glycosides occur as mixtures of homologs. Proper interpretation of the MS-MS or collisional activation decomposition spectra often allows the homology to be located. In addition to the simple and highly selective fragmentations observed in this combined experiment, FAB and MS-MS also remove interference caused by the ubiquitous matrix ions which are desorbed by FAB. PMID:3728980

Crow, F W; Tomer, K B; Looker, J H; Gross, M L

1986-06-01

276

Detection of poisoning by plant-origin cardiac glycoside with the Abbott TDx analyzer.  

PubMed

Cardiac glycoside poisoning caused by ingestion of plant material is common in tropical and sub-tropical areas. In evaluating the use of the Abbott TDx Digoxin II assay to detect such cases of poisoning, we found it a rapid and convenient method for confirming the ingestion of glycosides from the plants Nerium oleander, Thevetia peruviana, and Adonis microcarpa, and from the toad Bufo marinus. Here we report some clinical cases illustrating our experience with the use of this assay, and describe results of cross-reactivity studies with compounds structurally similar to digoxin. Because of the competitive nature of the immunoassay as well as the complexity of the mixture of cross-reacting cardiac glycosides present in the plant material, the measured apparent digoxin concentration is not linearly related to the cardiac glycoside concentration. PMID:2914377

Cheung, K; Hinds, J A; Duffy, P

1989-02-01

277

Two new cycloartane glycosides from the underground parts of Aquilegia vulgaris.  

PubMed

Two new cycloartane glycosides, named aquilegiosides K and L, have been isolated from the dried underground parts of Aquilegia vulgaris. Their structures were determined by two dimensional (2D) NMR spectroscopic analysis and chemical evidence. PMID:18981620

Yoshimitsu, Hitoshi; Nishida, Makiko; Nohara, Toshihiro

2008-11-01

278

Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases.  

PubMed

A small series of C-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which ?-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity. PMID:23010455

Riafrecha, Leonardo E; Rodríguez, Oscar M; Vullo, Daniela; Supuran, Claudiu T; Colinas, Pedro A

2013-03-15

279

Relationship between the chemical structure and pharmacological action of cardiac glycosides of the strophanthidin series  

Microsoft Academic Search

The possibility has been shown of finding and creating highly effective cardiotonic drugs for pediatric practice on the basis of cardenolides obtained by the chemical transformation of natural cardiac glycosides.

S. S. Azizova; Z. A. Khushbaktova; Z. Paluanova; N. Sh. Pal'yants

1995-01-01

280

An investigation of the kinetic and anti-angiogenic properties of plant glycoside inhibitors of thymidine phosphorylase.  

PubMed

We investigated the potential of symplocomoside (1) and symponoside (2), glycosides isolated from the bark of Symplocos racemosa to inhibit thymidine phosphorylase (TP) activity and associated angiogenesis. Compound 1 was a reversible, noncompetitive inhibitor of deoxythymidine binding to TP (IC(50) = 65.45 +/- 5.08 microM; K(i) = 62.83 +/- 2.10 microM) and 2 was a reversible, uncompetitive inhibitor (IC(50) = 94.17 +/- 4.05 microM; K(i) = 101.95 +/- 1.65 microM). Molecular modeling analysis indicated that both compounds bound at the active site of the enzyme but not solely to amino acid residues involved in catalysis. Both compounds were active in in vitro angiogenic assays inhibiting endothelial cell migration and invasion in Matrigel, but did not inhibit growth factor-induced proliferation and were not cytotoxic. Compound 1 may have potential as an anti-angiogenic and anti-tumor agent. PMID:19219729

Hussain, S; Gaffney, J; Ahmed, N; Slevin, M; Iqbal Choudhary, M; Ahmad, V U; Qasmi, Z; Abbasi, M A

2009-01-01

281

Glycosides of megastigmane and of the simple alcohols from Alangium premnifolium.  

PubMed

From the water-soluble fraction of a methanol extract of leaves of Alangium premnifolium, two new megastigmane glycosides, alangionosides N and O, along with three known megastigmane glycosides, dendranthemoside A and alangionosides A and B, were isolated. Shimaurinosides A and B, xylopyranosyl(1-->6)glucopyranosides of simple alcohols were also found to be constituents of the water-soluble fraction. Structures were determined by spectroscopic analyses. PMID:8768324

Kijima, H; Otsuka, H; Ide, T; Ogimi, C; Hirata, E; Takushi, A; Takeda, Y

1996-06-01

282

New holostan-type triterpene glycosides from the sea cucumber Apostichopus japonicus.  

PubMed

Two new holostan-type glycosides, holotoxin D1 (1) and 25,26-dihydroxy-holotoxin A1 (2), together with two known analogues, stichlorosides C1 (3) and bivittoside D (4), were isolated from the sea cucumber Apostichopus japonicus Selenka. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. Glycosides 1 and 3 exhibited potent antifungal activity. PMID:23285801

Wang, Zenglei; Gong, Wei; Sun, Guoquan; Tang, Hua; Liu, Baoshu; Li, Ling; Yi, Yanghua; Zhang, Wen

2012-11-01

283

DPPH radical scavenging activity of two flavonol glycosides from Aconitum napellus sp. lusitanicum  

Microsoft Academic Search

The DPPH radical scavenging activity of two flavonol glycosides obtained from ethanolic extracts of Aconitum napellus sp. lusitanicum was studied. The results showed a high DPPH antiradical activity of compound 1 (quercetin 3-O-(6-trans-caffeoyl)-?-glucopyranosyl-(1?2)-?-glucopyranosyl-7-O-?-rhamnopyranoside) when compared with compound 2 (quercetin-3-sophoroside-7-rhamnopyranoside), rutin and ascorbic acid. The relationship between the caffeoyl and rhamnopyranoside groups in the flavonol glycosides structures and the DPPH antiradical

J. C. Luis; F. Valdés; R. Martín; A. J. Carmona; Jesús G. Díaz

2006-01-01

284

Synthesis of Double C-Glycoside Analogue of sTn  

PubMed Central

A sTn double C-glycoside, sTn analogue 2, was synthesized using samarium chemistry developed in our laboratory. Complications in the oxidation reaction affording aldehyde acceptor were overcome by double protection of amide and the use of a room-temperature ionic liquid as solvent. Studies are underway to conjugate the sTn double C-glycoside hapten 2 to KLH carrier protein for biological evaluation as a vaccine.

Ress, Dino K.; Baytas, Sultan N.; Wang, Qun; Munoz, Eva M.; Tokuzoki, Kazuo; Tomiyama, Hiroshi; Linhardt, Robert J.

2014-01-01

285

Peculiarities of diterpenoid steviol glycoside production in in vitro cultures of Stevia rebaudiana Bertoni  

Microsoft Academic Search

The composition and content of steviol-glycosides (SGs)1So named diterpenoid glycoside, having steviol as an aglycone.1 in in vitro cultures of stevia (Stevia rebaudiana Bertoni) were investigated. A comparative analysis of production of these compounds in intact plants, in vitro plants, dedifferentiated callus and suspension cultures, morphogenic callus and in vitro regenerated shoots were conducted. Qualitative composition of the SGs in

Nikolai Bondarev; Oxana Reshetnyak; Alexander Nosov

2001-01-01

286

Synthesis of bifunctional polymeric adsorbent and its application in purification of stevia glycosides  

Microsoft Academic Search

Polymeric adsorbents with both functions of adsorption and decolorization were synthesized by introducing quaternary ammonium groups (e.g. –N+(CH3)3 groups) into conventional resinic adsorbent used to adsorb stevia glycosides in production. The relation between the adsorption capacity of the bifunctional adsorbents for stevia glycosides and the structure of adsorbents, and that between the decolorization efficiency and the structure were investigated. The

Rongfu Shi; Mancai Xu; Zuoqing Shi; Yunge Fan; Xianzhi Guo; Yongning Liu; Chunhong Wang; Binglin He

2002-01-01

287

Spatial Organisation of Four Enzymes from Stevia rebaudiana that are Involved in Steviol Glycoside Synthesis  

Microsoft Academic Search

The sweet steviol glycosides found in the leaves of Stevia rebaudiana Bert. are derived from the diterpene steviol which is produced from a branch of the gibberellic acid (GA) biosynthetic pathway.\\u000a An understanding of the spatial organisation of the two pathways including subcellular compartmentation provides important\\u000a insight for the metabolic engineering of steviol glycosides as well as other secondary metabolites

Tania V. Humphrey; Alex S. Richman; Rima Menassa; Jim E. Brandle

2006-01-01

288

Analytical Procedures for Determination of Quercetin and its Glycosides in Plant Material  

Microsoft Academic Search

Quercetin and its glycosides are widely distributed in the plant kingdom and belong to the most abundant of the flavonoid molecules. Besides their important biological roles in plant pigmentation, these flavonols possess anti-cancer and anti-inflammatory properties, which are the consequence of their affinity for proteins and their anti-oxidant properties. The content of quercetin and its glycosides in different plants have

Magdalena Biesaga; Krystyna Pyrzynska

2009-01-01

289

Regeneration and cardiotonic glycoside production in Digitalis davisiana Heywood (Alanya Foxglove)  

Microsoft Academic Search

A high-frequency in vitro regeneration of Digitalis davisiana Heywood (Alanya foxglove) and cardiotonic glycoside production from both in vitro produced materials (regenerated plantlets\\u000a or germinated seedlings) and leaves of natural populations were obtained. Cardiac glycosides regulate heart rhythm and are\\u000a effective in cancer chemotherapy, in particular for prostate and breast cancer treatments. Testing six different types of\\u000a culture media revealed

Ekrem Gurel; Buhara Yucesan; Esra Aglic; Songul Gurel; Sandeep K. Verma; Munevver Sokmen; Atalay Sokmen

2011-01-01

290

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

PubMed Central

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.

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

2011-01-01

291

Processivity and Enzymatic Mode of a Glycoside Hydrolase Family 5 Endoglucanase from Volvariella volvacea  

PubMed Central

EG1 is a modular glycoside hydrolase family 5 endoglucanase from Volvariella volvacea consisting of an N-terminal carbohydrate-binding module (CBM1) and a catalytic domain (CD). The ratios of soluble to insoluble reducing sugar produced from filter paper after 8 and 24 h of exposure to EG1 were 6.66 and 8.56, respectively, suggesting that it is a processive endoglucanase. Three derivatives of EG1 containing a core domain only or additional CBMs were constructed in order to evaluate the contribution of the CBM to the processivity and enzymatic mode of EG1 under stationary and agitated conditions. All four enzymatic forms exhibited the same mode of action on both soluble and insoluble cellulosic substrates with cellobiose as a main end product. An additional CBM fused at either the N or C terminus reduced specific activity toward soluble and insoluble celluloses under stationary reaction conditions. Deletion of the CBM significantly decreased enzyme processivity. Insertion of an additional CBM also resulted in a dramatic decrease in processivity in enzyme-substrate reaction mixtures incubated for 0.5 h, but this effect was reversed when reactions were allowed to proceed for longer periods (24 h). Further significant differences were observed in the substrate adsorption/desorption patterns of EG1 and enzyme derivatives equipped with an additional CBM under agitated reaction conditions. An additional family 1 CBM improved EG1 processivity on insoluble cellulose under highly agitated conditions. Our data indicate a strong link between high adsorption levels and low desorption levels in the processivity of EG1 and possibly other processive endoglucanses.

Zheng, Fei

2013-01-01

292

"Ring opening-ring closure" strategy for the synthesis of aryl-C-glycosides.  

PubMed

A new "ring-opening-ring closure" strategy for the synthesis of aryl-C-glycosides was described. This strategy exploited the nickel-catalyzed regioselective ?-O elimination of glycals by reactions with various aryl boronic acids or potassium aryltrifluoroborates to yield the ring-opened products, which underwent the Lewis acid, protonic acid, PhSeCl, or NBS mediated ring closure reactions to afford diverse aryl-C-glycosides. After Lewis acids and protonic acids were screened, it was found that, starting from the ring-opened substrates, the Ph3PHBr or Sc(OTf)3 mediated ring closure reaction provided ?- or ?-preferred aryl-C-?(2,3)-glycosides, respectively. Furthermore, ?-D-phenyl-C-glycosides were successfully prepared via the PhSeCl-mediated cyclization reaction, whereas the ?-D-phenyl-C-glycoside was obtained via the NBS-mediated cyclization reaction. After removal of the 2-substituted functionalities by Bu3SnH/AIBN, the synthesis of 2-deoxy-aryl-C-glycosides was ultimately realized in a stereoselective manner. PMID:24773451

Liu, Chen-Fu; Xiong, De-Cai; Ye, Xin-Shan

2014-05-16

293

Antitrypanosomal isothiocyanate and thiocarbamate glycosides from Moringa peregrina.  

PubMed

O-Methyl (1), O-ethyl (2), and O-butyl (3) 4-[(?-L-rhamnosyloxy) benzyl] thiocarbamate (E), along with 4-(?-L-rhamnosyloxy) benzyl isothiocyanate (4) have been isolated from the aerial parts of Moringa peregrina. The compounds were tested for in vitro activity against Trypanosoma brucei rhodesiense and cytotoxicity in rat skeletal myoblasts (L6 cells). The most potent compound was 4 with an IC50 of 0.10 µM against T.b. rhodesiense and a selectivity index of 73, while the thiocarbamate glycosides 1, 2, and 3 showed only moderate activity. Intraperitoneal administration of 50 mg/kg body weight/day of 4 in the T.b. rhodesiense STIB 900 acute mouse model revealed significant in vivo toxicity. Administration of 10 mg/kg body weight/day resulted in a 95% reduction of parasitemia on day 7 postinfection, but did not cure the animals. Because of its high in vitro activity and its ability to irreversibly inhibit trypanothione reductase, an attractive parasite-specific target enzyme, 4-[(?-L-rhamnosyloxy) benzyl] isothiocyanate (4), can be considered as a lead structure for the development and characterization of novel antitrypanosomal drugs. PMID:24310210

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

2014-01-01

294

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina.  

PubMed

Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and chrysoeriol 7-glucuronide (12) by spectroscopic analysis. All compounds except for 1 and 2 were isolated for the first time from this plant. The antioxidant activity was evaluated by the ORAC(Oxygen Radical Absorbance Capacity) assay, which measures scavenging activity against peroxy radicals induced by 2,2'-azobis (2-methoxypropion-amidine) dihydrochloride, and the ORAC value is expressed as relative trolox equivalent. Compounds 2, 4, 5, 6, 8, and 12 exhibited potent antioxidant activity, and compounds 1, 11 had similar activity with trolox, whereas the other compounds showed weaker activity than trolox. PMID:19280150

Kwak, Jong Hwan; Kim, Hyun Jung; Lee, Kwang Ho; Kang, Se Chan; Zee, Ok Pyo

2009-02-01

295

Antioxidant lignans and chromone glycosides from Eurya japonica.  

PubMed

Four new 8,8',7,2'-lignans, (+)-ovafolinin B-9'-O-?-d-glucopyranoside (1), (-)-ovafolinin B-9'-O-?-d-glucopyranoside (2), (+)-ovafolinin E-9'-O-?-d-glucopyranoside (3), and (-)-ovafolinin E-9'-O-?-d-glucopyranoside (4), two neolignans, eusiderin N (5) and (7S,8R)-3,5,5'-trimethoxy-4',7-epoxy-8,3'-neolignan-9,9'-diol-4-O-?-d-xylopyranoside (6), and two new chromone glycosides, 5,7-dihydroxy-4H-chromen-4-one-3-O-?-d-glucopyranoside (7) and 5,7-dihydroxy-4H-chromen-4-one-3-O-?-d-xylopyranoside (8), together with 25 known compounds, were isolated from the stems of Eurya japonica. Structural elucidation of compounds 1-8 was established by spectroscopic methods, especially 2D NMR techniques, electronic circular dichroism data, and comparison with reported data. The isolates were evaluated for antioxidant and anti-NO production activities. Compounds 1, 2, 12-20, and 29 (ED50 23.40 ?M for 1) demonstrated potent antioxidant activity compared to the positive control ?-tocopherol (ED50 27.21 ?M). On the other hand, compounds 1, 2, 7-9, 12-20, and 32 showed only weak anti-NO production activity when compared to the positive control quercetin. PMID:23540981

Yang Kuo, Li-Ming; Zhang, Li-Jie; Huang, Hung-Tse; Lin, Zhi-Hu; Liaw, Chia-Ching; Cheng, Hui-Ling; Lee, Kuo-Hsiung; Morris-Natschke, Susan L; Kuo, Yao-Haur; Ho, Hsiu-O

2013-04-26

296

Three acylated glycosidic acid methyl esters and two acylated methyl glycosides generated from the convolvulin fraction of seeds of Quamoclit pennata by treatment with indium(III) chloride in methanol.  

PubMed

Treatment of the ether-insoluble resin glycoside (convolvulin) fraction from seeds of Quamoclit pennata (Convolvulaceae) with indium(III) chloride in methanol provided three oligoglycosides of hydroxy fatty acid (glycosidic acid) methyl esters and two methyl glycosides, which were partially acylated by a glycosidic acid, 7S-hydroxydecanoic acid 7-O-?-D-quinovopyranoside (quamoclinic acid B) and/or two organic acids, (E)-2-methylbut-2-enoic (tiglic) acid and/or 3R-hydroxy-2R-methylbutyric (nilic) acid. Their structures were elucidated on the basis of spectroscopic data and chemical conversions. PMID:23995359

Akiyama, Kousuke; Mineno, Tomoko; Okawa, Masafumi; Kinjo, Junei; Miyashita, Hiroyuki; Yoshimitsu, Hitoshi; Nohara, Toshihiro; Ono, Masateru

2013-01-01

297

A simple determination of steroidal alkaloid glycosides by thin-layer chromatography immunostaining using monoclonal antibody against solamargine  

Microsoft Academic Search

A method of determination for solasodine glycosides by using thin-layer chromatography (TLC) immunostaining was investigated. Solasodine glycosides separated by silica gel TLC were transferred to a polyvinylidene difluoride membrane. The membrane was treated with sodium periodate solution followed by bovine serum albumin (BSA), resulting in a solasodine glycoside-BSA conjugate. Conjugation was confirmed by matrix-assisted laser desorption\\/ionization mass spectrometry. Individual spots

Hiroyuki Tanaka; Waraporn Putalun; Chiyumi Tsuzaki; Yukihiro Shoyama

1997-01-01

298

Cardiotonic glycosides from the latex of naucleopsis mello-barretoi, a dart-poison plant from North-West Brazil  

Microsoft Academic Search

Poison scraped from blowpipe darts made by the Makti Indians of the Upper Rio Uneiuxi, Rio Negro basin, and prepared from\\u000a the latex of Naucleopsis mello-barretoi (Standl.) C. C. Berg, contained ca. 4.4% cardiotonic glycosides; one of the major glycosides present was?-antiarin.\\u000a \\u000a Latex fromN. mello-barretoi yielded ca. 1.3% of a complex mixture of cardiotonic glycosides; the major component was ?-antiarin

Norman G. Bisset; Peter J. Hylands

1977-01-01

299

Managing Reverse Logistics or Reversing Logistics Management?  

Microsoft Academic Search

In the past, supply chains were busy fine-tuning the logistics from raw material to the end customer. Today an increasing flow of products is going back in the chain. Thus, companies have to manage reverse logistics as well.This thesis contributes to a better understanding of reverse logistics. The thesis brings insights on reverse logistics decision-making and it lays down theoretical

Brito de M. P

2004-01-01

300

Bioprospecting metagenomics of decaying wood: mining for new glycoside hydrolases  

SciTech Connect

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.

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

301

Constituents of a fern, Diplazium subsinuatum. II. Structure elucidation of five new hopane-triterpene glycosides.  

PubMed

From whole fern, Diplazium subsinuatum (Wall. ex Hook. et Grev.) Tagawa, two new hopane-triterpene glycosides named diplaziosides III and IV were isolated, together with three new hopane glycosides with acetylated sugars. The structures of diplaziosides III and IV were established as (22S)-24-O-alpha-L-arabinofuranosyl-(1 --> 2)- [beta-D-glucopyranosyl-(1 --> 6)]-beta-D-glucopyranosyl-20 alpha-O-beta-D-glucopyranosyl-30-hydroxyhopan-28-oic acid (1) and (22R)-24-O-alpha-L-arabinofuranosyl-(1-->2)-[beta-D-glucopyranosyl-(1--> 6)]-beta-D-glucopyranosyl-30-carboxy-17-hydroxy-hopano-28,22-lacto ne (2), respectively, on the basis of spectral evidence. Diplazioside III (1) is novel not only in its glycoside structure, but also in its triterpene structure and moreover, 1 provides the first instance of a naturally occurring bisdesmoside with a hopane aglycone. The structures (3a, 3b, and 4a) of the acetylated glycosides were also elucidated, and this is the first report of naturally occurring acetates of hopane glycosides. PMID:9023965

Nakanishi, T; Inatomi, Y; Nishi, M; Murata, H; Inada, A

1997-01-01

302

Phenolic Glycosides with antiproteasomal activity from Centaurea urvillei DC. subsp. urvillei.  

PubMed

A new flavanone glycoside, naringenin-7-O-?-D-glucuronopyranoside, and a new flavonol glycoside, 6-hydroxykaempferol-7-O-?-D-glucuronopyranoside were isolated together with 12 known compounds, 5 flavone glycoside; hispidulin-7-O-?-D-glucuronopyranoside, apigenin-7-O-?-D-methylglucuronopyranoside, hispidulin-7-O-?-D-methylglucuronopyranoside, hispidulin-7-O-?-D-glucopyranoside, apigenin-7-O-?-D-glucopyranoside, a flavonol; kaempferol, two flavone; apigenin, and luteolin, a flavanone glycoside; eriodictyol-7-O-?-D-glucuronopyranoside, and three phenol glycoside; arbutin, salidroside, and 3,5-dihydroxyphenethyl alcohol-3-O-?-D-glucopyranoside from Centaurea urvillei subsp. urvillei. The structure elucidation of the new compounds was achieved by a combination of one- ((1)H and (13)C) and two-dimensional NMR techniques (G-COSY, G-HMQC, and G-HMBC) and LC-ESI-MS. The isolated compounds were tested for their antiproteasomal activity. The results indicated that kaempferol, a well known and widely distributed flavonoid in the plant kingdom, was the most active antiproteasomal agent, followed by apigenin, eriodictyol-7-O-?-D-glucuronopyranoside, 3,5-dihydroxyphenethyl alcohol-3-O-?-D-glucopyranoside, and salidroside, respectively. PMID:20937505

Gülcemal, Derya; Alanku?-Çal??kan, Ozgen; Karaalp, Canan; Ors, Ahmet Uygar; Ballar, Petek; Bedir, Erdal

2010-11-22

303

Glycosidation of fructose-containing disaccharides using MCM-41 material as the catalyst.  

PubMed

Glycosidation of saccharides combines the essential characteristics of two major renewable classes, viz. triglycerides and carbohydrates, leading to biofriendly surfactants and emulsifiers. The development of the alkylglycosides derived from reducing disaccharides has lagged, because no efficient synthesis was available. We have found that ordered mesoporous materials of the MCM-41 type are active and selective catalysts for the glycosidation of disaccharides containing fructose at the reducing end, i.e., isomaltulose, lactulose and leucrose. No alcoholysis or hydrolysis of the glycosidic bond was observed, demonstrating the mildness of the MCM-41 catalyst. Leucrose was found to be less reactive than the two other disaccharides, in accordance with the absence of furanose forms in leucrose. PMID:12433464

van der Heijden, Anneke M; Lee, Tsz Chung; van Rantwijk, Fred; van Bekkum, Herman

2002-11-19

304

Cucurbitane glycosides from unripe fruits of Lo Han Kuo (Siraitia grosvenori).  

PubMed

From the unripe fruits of Lo Han Kuo (Siraitia grosvenori), a Chinese medicinal plant, two new cucurbitane triterpene glycosides, 20-hydroxy-11-oxomogroside IA(1) (1) and 11-oxomogroside IIE (2), were isolated along with five known cucurbitane glycosides, 11-oxomogroside IA(1) (3), mogroside IIE (4), mogroside III (5), mogroside IVA (6), and mogroside V (7), and two flavonoid glycosides, kaempferol 7-O-alpha-L-rhamnopyranoside (8) and kaempferol 3,7-di-O-alpha-L-rhamnopyranoside (9). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods and by comparing with literature values. This paper describes the first investigation of unripe bitter Lo Han Kuo fruits. PMID:17015982

Li, Dianpeng; Ikeda, Tsuyoshi; Matsuoka, Nanae; Nohara, Toshihiro; Zhang, Hourui; Sakamoto, Tatsunori; Nonaka, Gen-Ichiro

2006-10-01

305

Synthesis and evaluation of benzophenone O-glycosides as ?-glucosidase inhibitors.  

PubMed

The first total synthesis of benzophenone O-glycosides (iriflophenone 2-O-?-L-rhamnopyranoside: 1 and aquilarisinin: 2) isolated from the leaves of Aquilaria sinensis and related new derivatives (3-12) was accomplished through suitable protecting group manipulations and glycosylation starting from commercially available L-rhamnose, D-glucose, D-galactose, D-mannose, D-xylose, and 1,3,5-trihydroxybenzene. All synthesized benzophenone O-glycosides were evaluated for their inhibitory activities against ?-glucosidase. Of these, benzophenone O-glycosides 4 and 10 exhibited the most potent inhibitory activity in vitro against ?-glucosidase with IC(50) values of 168.7 ± 13.9 and 210.1 ± 23.9 µM, respectively, when compared with that of the positive control acarbose with an IC(50) value of 569.3 ± 49.7 µM. PMID:22730155

Liu, Qingchao; Guo, Tiantian; Li, Wenhong; Li, Dong; Feng, Zili

2012-10-01

306

Partial characterization of a biologically active steroid glycoside isolated from the starfish Marthasterias glacialis  

PubMed Central

1. A steroid glycoside (M2), which induces avoidance and other reactions in the mollusc Buccinum undatum, has been isolated from extracts of the starfish Marthasterias glacialis by ion-exchange chromatography. 2. The steroid glycoside was homogeneous by t.l.c. and contained glucose, quinovose, fucose and sulphate in the molar proportions 1:2:1:1, in addition to a water-insoluble aglycone. 3. The aglycone was identified as a cholestane derivative containing an unusual ?24-23-ketone system, two secondary hydroxyl groups and an olefinic double bond, and had the molecular formula C27H42O3. 4. The rates of release of sugars and sulphate suggested that fucose was at the non-reducing end of the oligosaccharide, with glucose glycosidically linked to the steroid. The sulphate group appeared to be linked to the other hydroxyl group of the steroid.

Mackie, A. M.; Turner, A. B.

1970-01-01

307

Isolation and structural elucidation of novel cholestane glycosides and spirostane saponins from Polygonatum odoratum.  

PubMed

Much attention has been paid to cholestane-type steroidal glycosides because of their importance from the perspectives of both chemical diversity and significant biological activities. A phytochemical investigation of the rhizomes of Polygonatum odoratum (Liliaceae) resulted in the isolation of three novel cholestane-type steroidal glycosides (1-3) with unique ?(14,16)-unsaturated D-ring structures as well as two novel spirostane-type steroidal saponins (4 and 5) and three known steroidal glycosides (6-8). Their structures were determined by various spectroscopic methods and chemical reactions. Steroidal saponin 7 showed significant antifungal activity against Candida albicans JCM1542 (MIC 3.1 ?g/mL) and Aspergillus fumigatus JCM1738 (MIC 6.3 ?g/mL). PMID:24291419

Bai, Hong; Li, Wei; Zhao, Huanxin; Anzai, Yojiro; Li, Haiming; Guo, Huanjie; Kato, Fumio; Koike, Kazuo

2014-02-01

308

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

PubMed Central

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.

2014-01-01

309

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

PubMed

Fatsia japonica Decne. & Planch. is a triterpenoid glycoside-rich herb with anti-inflammatory activity for the treatment of rheumatoid arthritis. A method for quantitative analysis of the complex triterpenoid glycosides in this medicinal plant has not been established so far. In this study, a high performance liquid chromatography (HPLC) method was developed for simultaneous qualification of 11 glycosides in F. japonica. The analysis was performed on an ODS-2 Hypersil column (250mm×4.6mm, 5?m) with a binary gradient mobile phase of water and acetonitrile. The established HPLC method was validated in terms of linearity, sensitivity, stability, precision, accuracy, and recovery. Results showed that this method had good linearity with R(2) at 0.99992-0.99999 in the test range of 0.04-9.00?g/?L. The limit of detection (LOD) and limit of quantification (LOQ) for the standard compounds were 0.013-0.020?g/?L and 0.040-0.060?g/?L. The relative standard deviations (RSDs%) of run variations were 0.83-1.40% for intra-day and 0.84-3.59% for inter-day. The analyzed compounds in the samples were stable for at least 36h, and the spike recoveries of the detected glycosides were 99.67-103.11%. The developed HPLC method was successfully applied for the measurements of the contents of 11 triterpenoid glycoside in different parts of F. japonica. Taken together, the HPLC method newly developed in this study could be used for qualitative and quantitative analysis of the bioactive triterpenoid glycosides in F. japonica and its products. PMID:24176752

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

2014-01-01

310

Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.  

PubMed

Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside. PMID:24867410

Mandal, S; Nilsson, U J

2014-06-18

311

Novel sesquiterpenoid glycosides and sesquiterpenes from the roots of Illicium henryi.  

PubMed

Seven new sesquiterpenoid glycosides, consisting of one thapsan-type (1), two capnellane-type (2 and 3), four floridanolide sesquiterpene glycosides (4-7), and one new azulene-type sesquiterpene (8), along with six known sesquiterpenes (9-14) were isolated from the roots of Illicium henryi. The structures of 1-8 were elucidated by extensive spectroscopic analyses and chemical methods. The absolute configurations of 1, 2, and 8 were determined based on Rh2(OCOCF3)4-induced CD, Mo2(OAc)4-induced CD data, and calculated electronic circular dichroism (ECD), respectively. Compound 1 was found to exhibit weak neurotoxicant activity. PMID:23982881

Zhuang, Peng-Yu; Zhang, Gui-Jie; Wang, Xiao-Jing; Zhang, Yan; Yu, Shi-Shan; Ma, Shuang-Gang; Liu, Yun-Bao; Qu, Jing; Li, Yong; Chen, Nai-Hong

2013-10-01

312

A new biologically active flavone glycoside from the seeds of Cassia fistula (Linn.).  

PubMed

A new bioactive flavone glycoside 1 [mp 252-254 degrees C, C28H32O16, [M]+ 624 (EIMS)] was isolated from the acetone soluble fraction of the defatted seeds of Cassia fistula (Linn.). It was characterized as a new bioactive flavone glycoside 5,3',4'-tri-hydroxy-6-methoxy-7-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-beta-D-galactopyranoside by several colour reactions, spectral analysis and chemical degradations. Compound 1 showed anti-microbial activity. PMID:12608640

Yadava, R N; Verma, Vikash

2003-03-01

313

Cordifolide A, a sulfur-containing clerodane diterpene glycoside from Tinospora cordifolia.  

PubMed

Cordifolide A (1), a novel unprecedented sulfur-containing clerodane diterpene glycoside, together with other two new diterpene glycosides, cordifolides B (2) and C (3), and four known analogues, was isolated from a methanol-soluble extract of the stems of Tinospora cordifolia. The structures of the new compounds were determined on the basis of spectroscopic data interpretation, with that of cordifolide A (1) confirmed by a single-crystal X-ray crystallographic analysis. All isolates were evaluated for their in vitro immunomodulatory activity using mouse bone marrow-derived dentritic cells (BMDCs). PMID:22497272

Pan, Li; Terrazas, Cesar; Lezama-Davila, Claudio M; Rege, Nirmala; Gallucci, Judith C; Satoskar, Abhay R; Kinghorn, A Douglas

2012-04-20

314

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

PubMed Central

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.

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

2014-01-01

315

Steviol and Steviol-Glycoside: Glucosyltransferase Activities in Stevia rebaudiana Bertoni - Purification and Partial Characterization  

Microsoft Academic Search

The leaves of Stevia rebaudiana Bertoni contain sweet compounds which are glycosides of diterpene derivative steviol (ent-13-hydroxykaur-16-en-19-oic acid). Its main constituents are stevioside (triglucosylated steviol; 13-O-? -sophorosyl-19-O-?-glucosyl-steviol) and rebaudioside-A (tetraglucosylated steviol; 2?-O-?-glucosyl-13-O-?-sophorosyl- 19-O-?-glucosyl-steviol). From the extracts of S. rebaudiana Bertoni, two glucosyltransferases (GTases I and IIB) acting on steviol and steviol-glycosides were isolated, and another distinct activity (GTase IIA) acting

H. Shibata; Y. Sawa; T. Oka; S. Sonoke; K. K. Kim; M. Yoshioka

1995-01-01

316

INHIBITION OF INFLUENZA VIRUS MULTIPLICATION BY N-GLYCOSIDES OF BENZIMIDAZOLES  

PubMed Central

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-?-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 B12, 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.

Tamm, Igor; Folkers, Karl; Shunk, Clifford H.; Horsfall, Frank L.

1954-01-01

317

Antioxidative and hypocholesterolemic activities of water-soluble puerarin glycosides in HepG2 cells and in C57 BL\\/6J mice  

Microsoft Academic Search

Puerarin is an isoflavone derived from Kudzu roots and has antioxidant and hypocholesterolemic effects; however, its insolubility often limits its biological availability in vivo. Using a novel transglycosylation process, the solubility of puerarin glycosides was increased >100-fold, but it was not known whether these modified puerarin glycosides maintained biological activities. We found that water-soluble puerarin glycosides fully maintained antioxidant activities

Mi Ja Chung; Nak-Ju Sung; Cheon-Seok Park; Dong-Keon Kweon; Alberto Mantovani; Tae-Wha Moon; Sung-Joon Lee; Kwan-Hwa Park

2008-01-01

318

Five new resin glycoside derivatives isolated from the convolvulin fraction of seeds of Quamoclit pennata after treatment with indium(III) chloride in methanol.  

PubMed

Three new acylated methyl glycosides and two new acylated glycosidic acid methyl esters were isolated after treatment of the crude ether-insoluble resin glycoside (convolvulin) fraction from seeds of Quamoclit pennata BOJER (Convolvulaceae) with indium(III) chloride in methanol. Their structures were elucidated on the basis of spectroscopic data and chemical conversions. PMID:24390503

Akiyama, Kousuke; Yamamoto, Kazutaka; Mineno, Tomoko; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro; Ono, Masateru

2014-01-01

319

Protective effect of total flavonoid C-glycosides from Abrus mollis extract on lipopolysaccharide-induced lipotoxicity in mice.  

PubMed

Abrus mollis is a widely used traditional Chinese medicine for treating acute and chronic hepatitis, steatosis, and fibrosis. It was found that the total flavonoid C-glycosides from Abrus mollis extract (AME) showed potent antioxidant, anti-inflammatory, and hepatoprotective activities. To further investigate the hepatoprotective effect of AME and its possible mechanisms, lipopolysaccharide (LPS)-induced liver injury models were applied in the current study. The results indicated that AME significantly attenuated LPS-induced lipid accumulation in mouse primary hepatocytes as measured by triglyceride (TG) and total cholesterol (TC) assays and Oil Red O staining. Meanwhile, AME exerted a protective effect on LPS-induced liver injury as shown by decreased liver index, serum aminotransferase levels, and hepatic lipid accumulation. Real-time PCR and immunoblot data suggested that AME reversed the LPS-mediated lipid metabolism gene expression, such as sterol regulatory element-binding protein-1 (SREBP-1), fatty acid synthase (FAS), and acetyl-CoA carboxylase 1 (ACC1). In addition, LPS-induced overexpression of activating transcription factor 4 (ATF4), X-box-binding protein-1 (XBP-1), and C/EBP homologous protein (CHOP) were dramatically reversed by AME. Furthermore, AME also decreased the expression of LPS-enhanced interleukin-6 (IL-6) and cyclooxygenase-2 (COX-2). Here, it is demonstrated for the first time that AME ameliorated LPS-induced hepatic lipid accumulation and that this effect of AME can be attributed to its modulation of hepatic de novo fatty acid synthesis. This study also suggested that the hepatoprotective effect of AME may be related to its down-regulation of unfolded protein response (UPR) activation. PMID:24969528

Wang, Yun; Jiang, Zhen-Zhou; Chen, Mi; Wu, Mei-Juan; Guo, Hong-Li; Sun, Li-Xin; Wang, Hao; Zhang, Shuang; Wang, Tao; Zhang, Lu-Yong

2014-06-01

320

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

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

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

2008-11-01

321

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

PubMed

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-?-D-arabinopyranoside (71.7 mg), quercetin-3-O-?-L-arabinofuranoside (105.6 mg) and 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6''-O-galloyl)-?-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

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

2013-01-01

322

Reverse Correlation in Neurophysiology  

ERIC Educational Resources Information Center

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…

Ringach, Dario; Shapley, Robert

2004-01-01

323

Comprehensive characterization of Stevia rebaudiana using two-dimensional reversed-phase liquid chromatography/hydrophilic interaction liquid chromatography.  

PubMed

Two-dimensional reversed-phase liquid chromatography/hydrophilic interaction liquid chromatography (2D-RPLC/HILIC) system was successfully applied for comprehensive characterization of steviol glycosides from Stevia rebaudiana. The experiments were performed in offline mode using an XCharge C18 column in first dimension and an XAmide column in second dimension. In first dimension, preliminary separation of Stevia aqueous extract was accomplished and 30 fractions were collected. Then fractions 1-20 were selected for further purification and 13 compounds with high purity were obtained in second dimension. Comprehensive characterization of these compounds was completed by determination of their retention time, accurate molecular weight, diagnostic fragmentation ions, and nuclear magnetic resonance spectroscopy. As a result, all nine known steviol glycosides, as well as other four steviol glycosides were fully purified. The result demonstrated that this procedure is an effective approach for the preparative separation and comprehensive characterization of steviol glycosides in Stevia. This 2D-RPLC/HILIC method will be a promising tool for the purification of low-abundance compounds from natural products. PMID:22807364

Fu, Qing; Guo, Zhimou; Zhang, Xiuli; Liu, Yanfang; Liang, Xinmiao

2012-07-01

324

Quantum Operation Time Reversal  

SciTech Connect

The dynamics of an open quantum system can be described by a quantum operation: A linear, complete positive map of operators. Here, I exhibit a compact expression for the time reversal of a quantum operation, which is closely analogous to the time reversal of a classical Markov transition matrix. Since open quantum dynamics are stochastic, and not, in general, deterministic, the time reversal is not, in general, an inversion of the dynamics. Rather, the system relaxes toward equilibrium in both the forward and reverse time directions. The probability of a quantum trajectory and the conjugate, time reversed trajectory are related by the heat exchanged with the environment.

Crooks, Gavin E.

2008-03-25

325

Amberlyst 15–Catalyzed Efficient Synthesis of 2,3?Unsaturated Glycosides via Ferrier Rearrangement for Glycal  

Microsoft Academic Search

Amberlyst 15 serves as an inexpensive, effective, and environmentally friendly catalyst in converting 3,4,6?tri?O?acetyl?D?glucal (1) into 2,3?unsaturated O? and S?glycosides via Ferrier rearrangement in moderate to excellent yields with high ? selectivity.

Qiang Tian

2007-01-01

326

A strategy for the synthesis of anthraquinone-based aryl-C-glycosides.  

PubMed

An efficient and simple strategy for the synthesis of a diverse range of anthraquinone-based aryl-C-glycosides has been developed. It involves the sequential Diels-Alder reaction and oxidative aromatization with the preformed glycosyl diene and dienophiles. The glycosyl dienes were obtained from simple sugars by tandem one-pot substitution and elimination reaction. PMID:23617362

Anand, Namrata; Upadhyaya, Kapil; Ajay, Arya; Mahar, Rohit; Shukla, Sanjeev K; Kumar, Brijesh; Tripathi, Rama Pati

2013-05-17

327

Versatile Synthesis and Mechanism of Activation of S-Benzoxazolyl (SBox) Glycosides  

PubMed Central

As a part of a program for developing new efficient procedures for stereoselective glycosylation, a range of S-benzoxazolyl (SBox) glycosides have been synthesized. The mechanistic aspects of the SBox moiety activation for glycosylation via a variety of conceptually different pathways in the presence of thiophilic, electrophilic, or metal-based promoters have been investigated.

Kamat, Medha N.; Rath, Nigam P.; Demchenko, Alexei V.

2008-01-01

328

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

PubMed

Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence. PMID:19652412

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

2009-08-01

329

Phenylethanoid glycosides from Monochasma savatieri and their anticomplement activity through the classical pathway.  

PubMed

Five new phenylethanoid glycosides, savasides A-E (1-5), along with 6 known ones were isolated from the whole plant of Monochasma savatieri Franch. The structures of 1-5 were elucidated on the basis of spectroscopic data analysis. Moreover, all isolated compounds were evaluated for anticomplement activity through the classical pathway. PMID:22753034

Li, Min; Shi, Meng-Fan; Liu, Yan-Li; Xu, Qiong-Ming; Yang, Shi-Lin

2012-08-01

330

Release of glycosidically bound flavour compounds of Chardonnay by Oenococcus oeni during malolactic fermentation  

Microsoft Academic Search

Glycosidases, produced by Oenococcus oeni strain Lalvin EQ54 during malolactic fermentation (MLF) performed in a chemically defined wine (CDW) medium, contributed to the release of volatile aglycons from their glycosylated precursors, present in a Chardonnay wine glycosidic extract. The liberation of wine volatiles during MLF was limited by the low activity of these enzymes in this strain. Six different aglycons

Nadia D’Incecco; Eveline Bartowsky; Stella Kassara; Anna Lante; Paolo Spettoli; Paul Henschke

2004-01-01

331

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

PubMed

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

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

2004-10-01

332

Phenolic glycosides, a new class of human recombinant nucleotide pyrophosphatase phosphodiesterase-1 inhibitors  

Microsoft Academic Search

Cytotoxicity and kinetic studies of phenolic glycosides, benzoyl salireposide (1) and salireposide (2), isolated from Symplocos racemosa, were performed against phosphodiesterase I enzyme from snake venom and human nucleotide pyrophosphatase phosphodiesterase-1. Lineweaver–Burk and Dixon plots and their secondary replots showed that these compounds are pure noncompetitive inhibitors of both enzymes. Ki values of compounds 1 and 2 were found to

Muhammad Iqbal Choudhary; Naheed Fatima; Muhammad Athar Abbasi; Saima Jalil; Viqar Uddin Ahmad; Atta-ur-Rahman

2004-01-01

333

Sweet and Sweetness-inducing Activities of New Triterpene Glycosides, Strogins  

Microsoft Academic Search

In a previous study we isolated homologues of new oleanane-type triterpene glycosides from leaves of Staurogyne merguensis Kuntze and named them strogins. Strogins themselves have a sweet taste (sweet activity), which diminishes in a few minutes. Subsequent application of cold water to the mouth then elicits a sweet taste (sweetness-inducing activity). In the present study we systematically examined the properties

Daigo Sugita; Reiko Inoue; Yoshie Kurihara

1998-01-01

334

Fomitoside K, a New Lanostane Triterpene Glycoside from the Fruiting Body of Fomitopsis nigra  

PubMed Central

In an effort to identify the chemical constituents of fruiting bodies of Fomitopsis pinicola, a new lanostane triterpene glycoside, designated as fomitoside K, has been isolated from its methanolic extract. Its chemical structure was assigned on the basis of various spectroscopic studies.

Lee, In-Kyoung; Jung, Jin-Young; Yeom, Ji-Hee; Ki, Dae-Won; Lee, Myeong-Seok; Yeo, Woon-Hyung

2012-01-01

335

Fomitoside K, a New Lanostane Triterpene Glycoside from the Fruiting Body of Fomitopsis nigra.  

PubMed

In an effort to identify the chemical constituents of fruiting bodies of Fomitopsis pinicola, a new lanostane triterpene glycoside, designated as fomitoside K, has been isolated from its methanolic extract. Its chemical structure was assigned on the basis of various spectroscopic studies. PMID:22783139

Lee, In-Kyoung; Jung, Jin-Young; Yeom, Ji-Hee; Ki, Dae-Won; Lee, Myeong-Seok; Yeo, Woon-Hyung; Yun, Bong-Sik

2012-03-01

336

Enhanced profiling of flavonol glycosides in the fruits of sea buckthorn (Hippophae rhamnoides).  

PubMed

Use of enhanced LC-MS/MS methods to identify common glycosyl groups of flavonoid glycosides enabled better characterization of the flavonoids in fruits of sea buckthorn (Hippophae rhamnoides). The saccharide moieties of 48 flavonol O-glycosides detected in a methanol extract were identified by these methods. Several of the flavonol glycosides were acylated, two of which were isolated and found to be new compounds. Their structures were determined using spectroscopic and chemical methods as isorhamnetin 3-O-(6-O-E-sinapoyl-?-D-glucopyranosyl)-(1?2)-?-D-glucopyranoside-7-O-?-L-rhamnopyranoside (24) and isorhamnetin 3-O-(6-O-E-feruloyl-?-D-glucopyranosyl)-(1?2)-?-D-glucopyranoside-7-O-?-L-rhamnopyranoside (30). Analysis of the acylated glycosyl groups of 24 and 30 by serial mass spectrometry provided evidence to suggest the acylation position of 11 other minor flavonol glycosides acylated with hydroxycinnamic or hydroxybenzoic acids. The nitric oxide scavenging activities of 24 and 30 were compared with those of other flavonoids and with ascorbic acid and the potassium salt of 2-(4-carboxyphenyl)-4,5-dihydro-4,4,5,5-tetramethyl-1H-imidazolyl-1-oxy-3-oxide (carboxy-PTIO). PMID:23517173

Fang, Rui; Veitch, Nigel C; Kite, Geoffrey C; Porter, Elaine A; Simmonds, Monique S J

2013-04-24

337

Two new C21 steroidal glycosides from Marsdenia tenacissima (ROXB.) WIGHT et ARN.  

PubMed

Two new C(21) steroidal glycosides, tenacissoside L (1), tenacissoside M (2), were isolated from the stems of Marsdenia tenacissima (ROXB.) WIGHT et ARN. Their structures were elucidated, respectively, by means of chemical and spectral data, including ESI-MS, HR-ESI-MS, 1D-NMR and 2D-NMR. PMID:16651770

Wang, Shu; Lai, Yu-Han; Tian, Bao; Yang, Lin

2006-05-01

338

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

PubMed Central

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).

2012-01-01

339

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

PubMed

Eugenol, a volatile phenylpropene found in many plant species, exhibits antibacterial and acaricidal activities. This study attempted to modify the production of eugenol and its glycosides by introducing petunia coniferyl alcohol acetyltransferase (PhCFAT) and eugenol synthase (PhEGS) into hybrid aspen. Gas chromatography analyses revealed that wild-type hybrid aspen produced small amount of eugenol in leaves. The heterologous overexpression of PhCFAT alone resulted in up to 7-fold higher eugenol levels and up to 22-fold eugenol glycoside levels in leaves of transgenic aspen plants. The overexpression of PhEGS alone resulted in a subtle increase in either eugenol or eugenol glycosides, and the overexpression of both PhCFAT and PhEGS resulted in significant increases in the levels of both eugenol and eugenol glycosides which were nonetheless lower than the increases seen with overexpression of PhCFAT alone. On the other hand, overexpression of PhCFAT in transgenic Arabidopsis and tobacco did not cause any synthesis of eugenol. These results indicate that aspen leaves, but not Arabidopsis and tobacco leaves, have a partially active pathway to eugenol that is limited by the level of CFAT activity and thus the flux of this pathway can be increased by the introduction of a single heterologous gene. PMID:23707945

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

2013-06-21

340

Protection against Amanita phalloides by the iridoid glycoside mixture of Picrorhiza kurroa (kutkin)  

Microsoft Academic Search

Survival of mice after lethal doses of a lyophilizate fromAmanita phalloides (‘death cap’) was markedly increased by pretreatment with single doses of kutkin, a mixture of iridoid glycosides picroside I and kutkoside isolated from the roots ofPicrorhiza kurroa. The protective effect of kutkin was comparable to that of silibinin. The curative efficacy of kutkin appeared to be slightly superior.

G. L. Floersheim; A. Bieri; R. Koenig; A. Pletscher

1990-01-01

341

Protection against Amanita phalloides by the iridoid glycoside mixture of Picrorhiza kurroa (kutkin).  

PubMed

Survival of mice after lethal doses of lyophilizate from Amanita phalloides ('death cap') was markedly increased by pretreatment with single doses of kutkin, a mixture of iridoid glycosides picroside I and kutkoside isolated from the roots of Picrorhiza kurroa. The protective effect of kutkin was comparable to that of silibinin. The curative efficacy of kutkin appeared to be slightly superior. PMID:2339676

Floersheim, G L; Bieri, A; Koenig, R; Pletscher, A

1990-03-01

342

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

PubMed Central

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.

2012-01-01

343

Hypervalent iodine mediated synthesis of C-2 deoxy glycosides and amino acid glycoconjugates.  

PubMed

A simple, efficient, and practical method for the synthesis of C-2 deoxy-2-iodo glycoconjugates in self-assembled structures was found using PhI(OCOR)2. 2-Iodo glycoserinyl esters were intramolecularly converted into 2-iodo serinyl glycosides which upon dehalogenation gave C-2 deoxy amino acid glycoconjugates. PMID:24754460

Islam, Maidul; Tirukoti, Nishanth D; Nandi, Shyamapada; Hotha, Srinivas

2014-05-16

344

Phenolics, fibre, alkaloids, saponins, and cyanogenic glycosides in a seasonal cloud forest in India  

Microsoft Academic Search

We investigated secondary compounds in ephemeral and non-ephemeral parts of trees and lianas of a seasonal cloud forest in the Western Ghats of India. We measured astringency, phenolic content, condensed tannins, gallotannins, ellagitannins, and fibre, and also screened for alkaloids, saponins and cyanogenic glycosides in 271 plant parts across 33 tree and 10 liana species which constituted more than 90%

S Mali; R. M Borges

2003-01-01

345

Aspergillus niger DLFCC-90 Rhamnoside Hydrolase, a New Type of Flavonoid Glycoside Hydrolase  

PubMed Central

A novel rutin-?-l-rhamnosidase hydrolyzing ?-l-rhamnoside of rutin, naringin, and hesperidin was purified and characterized from Aspergillus niger DLFCC-90, and the gene encoding this enzyme, which is highly homologous to the ?-amylase gene, was cloned and expressed in Pichia pastoris GS115. The novel enzyme was classified in glycoside-hydrolase (GH) family 13.

Liu, Tingqiang; Zhang, Chunzhi; Lu, Mingchun; Piao, Yongzhe; Ohba, Masashi; Tang, Minqian; Yuan, Xiaodong; Wei, Shenghua; Wang, Kan; Ma, Anzhou; Feng, Xue; Qin, Siqing; Mukai, Chisato; Tsuji, Akira

2012-01-01

346

Two new dimeric secoiridoid glycosides from the fruits of Ligustrum lucidum.  

PubMed

Two new secoiridoid glycosides, ligusides A and B (1 and 2), as well as seven known compounds (3-9), were isolated from the fruits of Ligustrum lucidum. Their structures were elucidated on the basis of spectroscopic and chemical analysis. PMID:20706905

Huang, Xiao-Jun; Wang, Ying; Yin, Zhi-Qi; Ye, Wen-Cai

2010-08-01

347

Steviol Glycosides from Stevia: Biosynthesis Pathway Review and their Application in Foods and Medicine  

Microsoft Academic Search

Stevia rebaudiana, a perennial herb from Asteraceae family, is known to the scientific world for its sweetness and steviol glycosides (SGs). SGs are the secondary metabolites responsible for the sweetness of Stevia. They are synthesized by SG biosynthesis pathway operating in the leaves. Most of genes encoding the enzymes of this pathway have been cloned and characterized from Stevia. Out

Sudesh Yadav; Praveen Guleria

2011-01-01

348

Utilisation of steviol glycosides from Stevia rebaudiana (Bertoni) by lactobacilli and bifidobacteria in in vitro conditions.  

PubMed

In the current study, eight strains of bifidobacteria and seven strains of lactobacilli were tested for their ability to grow in the presence of rebaudioside A and steviol glycosides from the sweetener Natusweet M001 originating from herb Stevia rebaudiana (Bertoni). Stevia is gaining popularity as a natural, non-caloric sugar substitute, and recently, it was allowed as a food additive by European Union too. Utilisation of steviol glycosides by intestinal microbiota suggests that they might have potential prebiotic effect. Based on the evaluation of bacterial density and pH values in our in vitro study, it was found that lactobacilli and bifidobacteria tested were able to utilise steviol glycosides as a carbon source only to a very limited extent. All strains tested showed significantly lower change in the absorbance A540 (P?glycosides. PMID:24249153

Kunová, Gabriela; Rada, Vojt?ch; Vidaillac, Adrien; Lisova, Ivana

2014-05-01

349

Method validation of a survey of thevetia cardiac glycosides in serum samples.  

PubMed

A sensitive and specific liquid chromatography tandem mass spectrometry (HPLC-ESI(+)-MS/MS) procedure was developed and validated for the identification and quantification of thevetin B and further cardiac glycosides in human serum. The seeds of Yellow Oleander (Thevetia peruviana) contain cardiac glycosides that can cause serious intoxication. A mixture of six thevetia glycosides was extracted from these seeds and characterized. Thevetin B, isolated and efficiently purified from that mixture, is the main component and can be used as evidence. Solid phase extraction (SPE) proved to be an effective sample preparation method. Digoxin-d3 was used as the internal standard. Although ion suppression occurs, the limit of detection (LOD) is 0.27 ng/ml serum for thevetin B. Recovery is higher than 94%, and accuracy and precision were proficient. Method refinement was carried out with regard to developing a general screening method for cardiac glycosides. The assay is linear over the range of 0.5-8 ng/ml serum. Finally, the method was applied to a case of thevetia seed ingestion. PMID:21376490

Kohls, Sarah; Scholz-Böttcher, Barbara; Rullkötter, Jürgen; Teske, Jörg

2012-02-10

350

Hydrolysis and transformation of terpene glycosides from muscat must by different yeast species  

Microsoft Academic Search

The purpose of this study was to verify whether both wine yeasts belonging to different species (Metschnikowia pulcherrima (2), Debaryomyces hansenii, Kluyveromyces thermotolerans, Saccharomyces cerevisiae (3), Hanseniaspora uvarum, Pichia kluyveri) and a non-wine yeast (Candida molischiana), were able to hydrolyse the terpenoids, norisoprenoids and benzenoids glycosides occurring in Muscat must and transform the produced aglycons. The results obtained confirmed the

M Fernández-González; R Di Stefano; A Briones

2003-01-01

351

Gas Chromatographic – Mass Spectrometric Cardiotonic Glycosides Detection in Equine Urine Doping Analysis  

Microsoft Academic Search

A screening method for the detection of cardiotonic glycosides in horse’s urine is presented in this paper. This method is based on the detection by gas chromatography -mass spectrometry (GC -MS) and gas chromatography -high resolution mass spectrometry (GC -HRMS) of the trimethylsilyl (TMS) derivatives of the aglycon moieties of these compounds after solid phase extraction and methanolysis, according to

P. Kiousi; Y. S. Angelis; M. Koupparis; D. Kouretas; N. Diakakis; A. Desiris; C. G. Georgakopoulos

2004-01-01

352

Flavonoid glycosides extracted from hop (Humulus lupulus L.) as inhibitors of chemical mediator release from human basophilic KU812 cells.  

PubMed

The antiallergic properties of hop water extract (HWE) were studied by evaluating histamine release from human basophilic KU812 cells induced by calcium ionophore A23187. HWE significantly inhibited histamine release, but boiling water extract and chloroform-methanol extract did not show any inhibitory effect on it. A 50% methanol-eluted fraction separated from HWE by XAD-4 column chromatography (MFH) had a strong inhibitory effect as compared with HWE. Quercetin glycosides and kaempherol glycosides were identified in MFH, of which quercetin glycosides contributed to the inhibition of histamine release. Most quercetin in HWE existed in glycoside form and its quercetin content, obtained by acid hydrolysis, was about 200 mug/g. HWE and MFH significantly inhibited protein kinase C, which plays a pivotal role in the degranulation of chemical mediators. These results indicate that HWE can inhibit type-I allergic reactions. PMID:17151464

Segawa, Shuichi; Yasui, Kazuhisa; Takata, Yoshihiro; Kurihara, Toshio; Kaneda, Hirotaka; Watari, Junji

2006-12-01

353

[Isolation of polymeric glycoprotein complexes of enveloped viruses using the Quill A glycoside and a study of their immunogenic activity].  

PubMed

Specific multimer complexes of glycoproteins of enveloped viruses were prepared by treatment of suspensions of purified concentrated virus with a non-ionic detergent MECK mixed with 0.2% glycoside Quil A. Mixed complexes of glycoproteins with glycoside Quil A were formed upon removal of the detergent from the mixture of solubilized glycoproteins and glycoside Quil A. According to the results of electron microscopy, the formed complexes differed morphologically from the conventional micelles of glycoproteins and presented spherical reticular structures 20-30 nm in diameter. The immunogenic potency of the complexes was much higher than that of virus particles and micelles of purified glycoproteins and was comparable to the immunogenic potency of glycoproteins mixed with complete Freund adjuvant. The protective activity of the complex of protein G of rabies virus with glycoside Quil A was higher than that of the subunit rabies vaccine adsorbed on aluminium hydroxide. PMID:2823481

Berezin, V E; Za?des, V E; Grigor'ev, V B; Klimenko, S M; Zhdanov, V M

1987-01-01

354

Seasonal variation of alkaloids of Adhatoda vasica and detection of glycosides and N-Oxides of vasicine and vasicinone.  

PubMed

The distribution pattern of the alkaloids of A. Vasica has been studied with change of season. The study also resulted in the detection of glycosides and N-oxides of vasicine and vasicinone. PMID:17404955

Pandita, K; Bhatia, M S; Thappa, R K; Agarwal, S G; Dhar, K L; Atal, C K

1983-06-01

355

Liquid chromatography combined with thermospray and continuous-flow fast atom bombardment mass spectrometry of glycosides in crude plant extracts  

Microsoft Academic Search

In crude plant extracts, constituents of biological or pharmaceutical interest often exist in the form of glycosides. Off-line mass spectral investigations of these metabolites require soft ionisation techniques such as desorption chemical ionisation (DCI) or fast atom bombardment (FAB) if information on molecular mass or sugar sequence is desired. In LC-MS, glycosides can be ionised by using thermospray (TSP), continuous-flow

J.-L. Wolfender; K. Hostettmann; F. Abe; T. Nagao; H. Okabe; T. Yamauchi

1995-01-01

356

Effects of quercetin and quercetin-3- O-glycosides on oxidative damage in rat C6 glioma cells  

Microsoft Academic Search

Flavonoids are reported to be powerful antioxidants in cell free systems. They naturally occur as glycosides rather than as aglycon. In this study the ability of the flavonoid quercetin and its glycosides, quercetin-3-O-rutinoside (rutin), quercetin-3-O-glucoside and quercetin-3-O-(6?-O-acetyl)-glucoside, to protect in vitro rat C6 glioma cells from oxidative damage induced by cumene hydroperoxide was investigated. Cumene hydroperoxide induced cell death and

Ma?gorzata Zieli?ska; Michael Gülden; Hasso Seibert

2003-01-01

357

Molluscicidal activity of cardiac glycosides from Nerium indicum against Pomacea canaliculata and its implications for the mechanisms of toxicity  

Microsoft Academic Search

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 LC50 value of cardiac glycosides against GAS was time dependent and the LC50 value at 96h was as low as 3.71mg\\/L, which was comparable with that of metaldehyde at 72h (3.88mg\\/L). These

Lingpeng Dai; Wanxian Wang; Xinjiao Dong; Renyong Hu; Xuyang Nan

2011-01-01

358

Chemical composition and antioxidant effect of glycosidically bound volatile compounds from oregano ( Origanum vulgare L. ssp. hirtum)  

Microsoft Academic Search

The present work examines the content and chemical composition of the glycosidically bound volatiles from oregano as well as their antioxidative properties. The glycosidically bound volatiles amounted to 20 mg kg?1 in dried leaves and flowers of oregano. Fourteen volatile aglycones were identified with thymoquinone as the major component. Other important aglycones were benzyl alcohol, eugenol, 2-phenyl-ethanol, thymol, 3-hexen-1-ol and

M Milos; J Mastelic; I Jerkovic

2000-01-01

359

Geomagnetism II: Magnetic Reversals  

NSDL National Science Digital Library

This is an activity about the periodic reversals of Earth's magnetic field. Learners will graph the frequency of magnetic pole reversals over the past 800,000 years and investigate answers to questions using the graphed data. This is Activity 8 in the Exploring Magnetism on Earth teachers guide.

360

Towards a molecular-level theory of carbohydrate processivity in glycoside hydrolases.  

PubMed

Polysaccharide depolymerization in nature is primarily accomplished by processive glycoside hydrolases (GHs), which abstract single carbohydrate chains from polymer crystals and cleave glycosidic linkages without dissociating after each catalytic event. Understanding the molecular-level features and structural aspects of processivity is of importance due to the prevalence of processive GHs in biomass-degrading enzyme cocktails. Here, we describe recent advances towards the development of a molecular-level theory of processivity for cellulolytic and chitinolytic enzymes, including the development of novel methods for measuring rates of key steps in processive action and insights gained from structural and computational studies. Overall, we present a framework for developing structure-function relationships in processive GHs and outline additional progress towards developing a fundamental understanding of these industrially important enzymes. PMID:24863902

Beckham, Gregg T; Stĺhlberg, Jerry; Knott, Brandon C; Himmel, Michael E; Crowley, Michael F; Sandgren, Mats; Sřrlie, Morten; Payne, Christina M

2014-06-01

361

[Pharmacological activity of dihydroflavonol glycoside isolated from the plant Eupatorium micranthum Less].  

PubMed

The aim of the work was the investigation of pharmacological activity of unique dihydroflavonol glycoside, micranthoside, extracted from the leaves Eupatorium micranthum Less. introduced into Georgia. Mature human T-cell leukemia cell lines (Jurkat) were analyzed in the study under the modeled oxidative stress. For modelling of oxidative stress 30% hydrogen peroxide (H(2)O(2)) (Sigma) (100 microM) was added to Jurkat cell incubation suspension with subsequent incubation for 24, 48 h. Under the effect of H(2)O(2) there was significant elevation of superoxide and peroxyl radical levels, as well as free NO levels, and reduced antioxidant enzyme SOD activity. It was shown that dihydroflavonol glycoside, micranthoside, extragated from Eupatorium micranthum Less., has marked antioxidant properties, it inhibits hyperproduction of reactive oxygen species, and protects cells against oxidative damage, stimulates cell proliferation and inhibits necrosis in cell line. PMID:18487695

Sagare?shvili, T G; Mikautadze, M M; Intskirveli, N A; Enukidze, M G; Machavariani, M G

2008-04-01

362

Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L.  

PubMed

Chemical investigation of the pollen grain collected from male plants of Cannabis sativa L. resulted in the isolation for the first time of two flavonol glycosides from the methanol extract, and the identification of 16 cannabinoids in the hexane extract. The two glycosides were identified as kaempferol 3-O-sophoroside and quercetin 3-O-sophoroside by spectroscopic methods including high-field two-dimensional NMR experiments. The characterisation of each cannabinoid was performed by GC-FID and GC-MS analyses and by comparison with both available reference cannabinoids and reported data. The identified cannabinoids were delta9-tetrahydrocannabiorcol, cannabidivarin, cannabicitran, delta9-tetrahydrocannabivarin, cannabicyclol, cannabidiol, cannabichromene, delta9-tetrahydrocannabinol, cannabigerol, cannabinol, dihydrocannabinol, cannabielsoin, 6a, 7, 10a-trihydroxytetrahydrocannabinol, 9, 10-epoxycannabitriol, 10-O-ethylcannabitriol, and 7, 8-dehydro-10-O-ethylcannabitriol. PMID:15688956

Ross, Samir A; ElSohly, Mahmoud A; Sultana, Gazi N N; Mehmedic, Zlatko; Hossain, Chowdhury F; Chandra, Suman

2005-01-01

363

Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves.  

PubMed

An investigation of methanolic extract of Warburgia stuhlmannii leaves has led to the isolation of two new drimane-type sesquiterpene glycosides characterized as mukaadial 6-O-beta-D-glucopyranoside, mukaadial 6-O-alpha-L-rhamnopyranoside together with two other novel flavonol glycosides identified as 3',5'-O-dimethylmyricetin 3-O-beta-D-2",3"-diacetylglucopyranoside and 3'-O-methylquercetin 3-O-beta-D-2",3",4"-triacetylglucopyranoside. The known compounds; mukaadial, deacetylugandensolide, quercetin, kaempferol, kaempferol 3-O-alpha-L-rhamnopyranoside, quercetin 3-O-beta-D-glucopyranoside, kaempferol 7-O-beta-D-glucopyranoside, myricetin 3-O-alpha-L-rhamnopyranoside, quercetin 3-O-alpha-L-rhamnopyranoside, quercetin 3-O-sophoroside and isorhamnetin 3-O-beta-D-glucopyranoside were also isolated from the same extract. PMID:12770606

Manguro, Lawrence O Arot; Ugi, Ivar; Hermann, Rudolf; Lemmen, Peter

2003-06-01

364

Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves  

Microsoft Academic Search

An investigation of methanolic extract of Warburgia stuhlmannii leaves has led to the isolation of two new drimane-type sesquiterpene glycosides characterized as mukaadial 6-O-?-d-glucopyranoside, mukaadial 6-O-?-l-rhamnopyranoside together with two other novel flavonol glycosides identified as 3?,5?-O-dimethylmyricetin 3-O-?-d-2?,3?-diacetylglucopyranoside and 3?-O-methylquercetin 3-O-?-d-2?,3?,4?-triacetylglucopyranoside. The known compounds; mukaadial, deacetylugandensolide, quercetin, kaempferol, kaempferol 3-O-?-l-rhamnopyranoside, quercetin 3-O-?-d-glucopyranoside, kaempferol 7-O-?-d-glucopyranoside, myricetin 3-O-?-l-rhamnopyranoside, quercetin 3-O-?-l-rhamnopyranoside, quercetin 3-O-sophoroside and

Lawrence O. Arot Manguro; Ivar Ugi; Rudolf Hermann; Peter Lemmen

2003-01-01

365

Phenolic glycosides from Lindera fruticosa root and their inhibitory activity on osteoclast differentiation.  

PubMed

Two new compounds were found in the phenolic glycosides isolated from the roots of Lindera fruticosa: 5-O-[beta-D-apiofuranosyl-(1''-->2')-O-beta-D-xylopyranosyl]gentisic acid-7,5''-ester (3), named linderofruticoside A; and 5-O-[beta-D-apiofuranosyl-(1''-->3')-O-beta-D-xylopyranosyl]gentisic acid methyl ester (4), linderofruticoside B. Two previously known phenolic glycosides were also identified: beta-D-(3,4-disinapoyl)fructofuranosyl-alpha-D-(6-sinapoyl)glucopyranoside (1) and beta-D-(3-sinapoyl)fructofuranosyl-alpha-D-(6-sinapoyl)glucopyranoside (2). Compounds 1 and 2 inhibited osteoclast differentiation in a dose-dependent manner at concentrations higher than 1.04 microM and 0.132 microM, respectively. PMID:18451563

Song, Myoung-Chong; Nigussie, Fikru; Yang, Hye-Joung; Kim, Hong-Hee; Kim, Ji-Young; Chung, Dae-Kyun; Baek, Nam-In

2008-05-01

366

Hypoglycemic effects of a sesquiterpene glycoside isolated from leaves of loquat (Eriobotrya japonica (Thunb.) Lindl.).  

PubMed

Sesquiterpene glycoside, nerolidol-3-O-alpha-l-rhamnopyranosyl(1-->4)-alpha-l-rhamnopyranosyl(1-->2)-[alpha-l-rhamnopyranosyl(1-->6)]-beta-d-glucopyranoside was isolated from dried leaves of loquat [Eriobotrya japonica (Thunb.) Lindl., Rosaceae]. Hypoglycemic effects of this natural product were assessed in normal and alloxan-diabetic mice model. Animals received orally administration of the sesquiterpene glycoside in dose of 25 and 75 mg/kg. The anti-hyperglycemic effect was compared with gliclazide's. The dose of 25 and 75 mg/kg both exerted a significant (p<0.05) hypoglycemic effect in alloxan-diabetic mice throughout the test and a slight effect in normal mice. PMID:17291739

Chen, J; Li, W L; Wu, J L; Ren, B R; Zhang, H Q

2008-01-01

367

Comparison of the conformational properties of carbasugars and glycosides: the role of the endocyclic oxygen.  

PubMed

A series of carbasugars were prepared and their conformational properties studied by means of NMR spectroscopy. The results were compared to those previously found for O-, S-, and C-?-glycoside analogs. While the rotational populations of the hydroxymethyl group in O-, S-, and C-glycosides are known to depend on the structural nature of their aglycon, in carbasugars it proved to be independent of the pseudo-aglycon. This result confirms that endocyclic oxygen is necessary for the observed relationship between the structure of the aglycon and the rotational populations of the hydroxymethyl group, and indicates that the stereoelectronic exo-anomeric effect is mainly responsible for such conformational dependence. PMID:22444323

Mayato, Carlos; Dorta, Rosa L; Palazón, José M; Vázquez, Jesús T

2012-05-01

368

Three new resin glycosides and a new tetrahydropyran derivative from the seeds of Quamoclit pennata.  

PubMed

Three new resin glycosides, quamoclins V (1), VI (2), and VII (3) and a new tetrahydropyran derivative, quamopyran (4), were isolated from the seeds of Quamoclit pennata BOJER (Convolvulaceae). The chemical structures of these compounds were determined primarily on the basis of spectroscopic data. The carboxyl group of the aglycone, 11S-convolvulinolic acid, of 1 and 2 was linked intermoleculary with a hydroxy group of the sugar moiety to form a macrocyclic ester structure, as in already known jalapins, and 3 was an acylated glycosidic acid methyl ester. All of the sugar moieties of 1-3 were acylated by one 2S-methylbutyric acid. Compound 4 was a diketone having a tetrahydropyran ring. PMID:22863715

Ono, Masateru; Takaki, Yoshinari; Takatsuji, Masamitsu; Akiyama, Kousuke; Okawa, Masafumi; Kinjo, Junei; Miyashita, Hiroyuki; Yoshimitsu, Hitoshi; Nohara, Toshihiro

2012-01-01

369

Calysolins V-IX, resin glycosides from Calystegia soldanella and their antiviral activity toward herpes.  

PubMed

Five new resin glycosides having macrolactone structures (jalapins), named calysolins V-IX (1-5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types-one having a 22-membered ring (1-4) and the other with a 27-membered ring (5). The sugar moieties of 1-5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1-5, together with calysolins I-IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity. PMID:24390499

Ono, Masateru; Takigawa, Ayako; Kanemaru, Yukiyo; Kawakami, Gen; Kabata, Kiyotaka; Okawa, Masafumi; Kinjo, Junei; Yokomizo, Kazumi; Yoshimitsu, Hitoshi; Nohara, Toshihiro

2014-01-01

370

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

PubMed

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

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

371

Cardiac glycoside-like structure and function of 5 beta,14 beta-pregnanes  

SciTech Connect

5 beta-Reduction and 14 beta-substitution convert the planar progesterone molecule to the cardiac glycoside configuration--A and D rings of the steroid moiety are bent toward the alpha-face relative to the B and C rings. Potency of the 5 beta,14 beta-derivative in a ({sup 3}H)ouabain binding assay or its ability to inhibit the sodium pump in red blood cells is enhanced by 3 beta-hydroxylation, 20 beta-hydroxylation, and 3 beta-glycosidation. Synthesis of 14,20 beta-dihydroxy-3 beta-(beta-D-glucopyranosyloxy)- 5 beta,14 beta-pregnane from digitoxin is described. The glucoside is 1/20 as potent as ouabain and elicits prominent, sustained, positive inotropy in isolated cardiac muscle.

Templeton, J.F.; Kumar, V.P.; Bose, D.; LaBella, F.S.

1989-08-01

372

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

PubMed Central

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 ?1- and ?2-isoforms of the Na/K pumps. The stimulation of IP appears to be through stimulation of the high glycoside affinity ?2-isoform and not the ?1-isoform because of the following: (1) regulatory signals that specifically increased activity of the ?2-isoform increased the amplitude of the stimulation; (2) regulatory signals that specifically altered the activity of the ?1-isoform did not affect the stimulation; (3) changes in [K+]o that affected activity of the ?1-isoform, but not the ?2-isoform, did not affect the stimulation; (4) myocytes from one group of guinea pigs expressed the ?1-isoform but not the ?2-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 ?2-isoform, then activity of the ?2-isoform increased by 107 ± 30%. In the guinea pig myocytes, nanomolar ouabain as well as DHO stimulated the ?2-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 ?1- and ?3-isoforms of the Na/K pumps, suggesting the other high glycoside affinity isoform (the ?3-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 ?2- and ?3-isoforms could be separated from that of the ?1-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.

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

2002-01-01

373

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

PubMed Central

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 11?-hydroxylase and steroid 17-alpha-monooxygenase, and weak inhibition of cytochrome P450 side chain cleavage enzyme and 21?-hydroxylase, but not 3?-hydroxysteroid dehydrogenase/isomerase.

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

2013-01-01

374

Pregnane glycosides interfere with steroidogenic enzymes to down-regulate corticosteroid production in human adrenocortical H295R cells.  

PubMed

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 11?-hydroxylase and steroid 17-alpha-monooxygenase, and weak inhibition of cytochrome P450 side chain cleavage enzyme and 21?-hydroxylase, but not 3?-hydroxysteroid dehydrogenase/isomerase. PMID:23065845

Komarnytsky, Slavko; Esposito, Debora; Poulev, Alexander; Raskin, Ilya

2013-05-01

375

A truncated driven Overhauser effect study of Adriamycin in water: Conformation of the glycosidic linkage  

NASA Astrophysics Data System (ADS)

Truncated driven nuclear Overhauser effect difference spectra have been used to ascertain the conformational characteristics of the glycosidic linkage of Adriamycin in aqueous solution. The "two-spin approximation" has been employed to evaluate the cross-relaxation rates between nearby protons and to obtain the relative internuclear distances. The rotational angles ? 1 = C(7)-O(7)-C(1')-(H1') and ? 2 = H(7)-C(7)-O(7)-C(1') have also been calculated.

Cirilli, M.; Giomini, M.; Giuliani, A. M.; Trotta, E.

376

Alangionosides G-M: glycosides of megastigmane derivatives from the leaves of Alangium premnifolium.  

PubMed

Phytochemical investigation of the 1-BuOH-soluble fraction of the MeOH extract of Alangium premnifolium resulted in the isolation of ten megastigmane glycosides, of which, two, (6R,9R)-3-oxo-alpha-ionol apiofuranosylglucopyranoside and roseoside with (6S,9R)-blumeol A as an aglycone were known. The structures of the eight new compounds were determined by spectroscopic methods. PMID:7553962

Otsuka, H; Yao, M; Kamada, K; Takeda, Y

1995-05-01

377

Effect of exogenous steroid glycosides on cultured cells of potato under oxidative stress  

Microsoft Academic Search

Low doses of furostanol glycosides (FG) were shown to elevate the activity of peroxidases (guaiacol-dependent and ascorbate\\u000a peroxidases) and reduce peroxidation of lipids (POL) below the control level in the cell culture of potato (Solanum tuberosum L.). Under oxidative stress (OS) induced by paraquat, FG protected the cell culture from injury with peroxidase activity\\u000a being high and POL level lower

L. A. Volkova; S. N. Maevskaya; A. B. Burgutin; A. M. Nosov

2007-01-01

378

Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogues.  

PubMed

The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected via the isopropylidene compound 33. In contrast to the benzoic acid riboside (28) the benzamide riboside (2) showed extremely high cytotoxicity at nanomolar concentrations to S49.1 lymphoma cells but only slightly increased dexamethasone toxicity. PMID:1738143

Krohn, K; Heins, H; Wielckens, K

1992-02-01

379

Neo-clerodane diterpenoids and phenylethanoid glycosides from Teucrium chamaedrys L  

Microsoft Academic Search

A neo-clerodane type diterpenoid, 12(S)-15,16-epoxy-19-hydroxy-neo-cleroda-13(16),14-dien-18,6?:20,12-diolide, and two phenylethanoid glycosides, teucrioside-3?-O-methylether and teucrioside-3?,4?-O-dimethylether were isolated from the aerial parts of Teucrium chamaedrys. Their structures were identified on the basis of extensive NMR spectra, LC-ESIMS analysis, and molecular modeling studies.

Erdal Bedir; Rangavalli Manyam; Ikhlas A Khan

2003-01-01

380

Rapid Separation and Determination of Four Phenylpropanoid Glycosides from T. chamaedrys by Capillary Electrophoresis Method  

Microsoft Academic Search

Summary A new capillary electrophoresis method was developed for the separation of four phenylpropanoid glycosides (teucrioside, verbascoside, teucrioside-3””- O-methyl ether and teucrioside-3””, 4””- O-dimethyl ether) from T. chamaedrys. The electrophoretic separation was performed using a 50 cm × 50 µm i.d. (41.5 cm effective length) fused silica capillary. A phosphate-borate buffer (pH 8.9) in 15% ( v\\/v) isopropanol was used

B. Avula; R. B. Manyam; E. Bedir; I. A. Khan

2003-01-01

381

Neo-clerodane diterpenoids and phenylethanoid glycosides from Teucrium chamaedrys L.  

PubMed

A neo-clerodane type diterpenoid, 12(S)-15,16-epoxy-19-hydroxy-neo-cleroda-13(16),14-dien-18,6alpha:20,12-diolide, and two phenylethanoid glycosides, teucrioside-3(IIII)-O-methylether and teucrioside-3(IIII),4(IIII)-O-dimethylether were isolated from the aerial parts of Teucrium chamaedrys. Their structures were identified on the basis of extensive NMR spectra, LC-ESIMS analysis, and molecular modeling studies. PMID:12895549

Bedir, Erdal; Manyam, Rangavalli; Khan, Ikhlas A

2003-08-01

382

Multi-Glycoside of Tripterygium wilfordii Hook f. Ameliorates Prolonged Mesangial Lesions in Experimental Progressive Glomerulonephritis  

Microsoft Academic Search

Background\\/Aims: Multi-glycoside from Tripterygium wilfordii Hook f. (GTW) is used for treatment of progressive glomerulonephritis (GN) in China. We have previously reported the beneficial effects of GTW on acute GN induced by an anti-Thy-1.1 monoclonal antibody (mAb). In the present study, the effect and potential mechanisms of GTW on the chronic irreversible model of GN were investigated. Methods: Progressive GN

Yigang Wan; Wei Sun; Huilan Zhang; Qiaojing Yan; Ping Chen; Chenhui Dou; Haiming Yang; Ming Ge

2010-01-01

383

Barlerisides A and B, new potent superoxide scavenging phenolic glycosides from Barleria acanthoides.  

PubMed

Barlerisides A (1) and B (2), new phenolic glycosides, have been isolated from the n-butanol soluble sub-fraction of Barleria acanthoides along with two known compounds acteoside (3) and p-hydroxycinnamic acid (4). Their structures have been assigned on the basis of spectral studies. Both 1 and 2 showed significant activity in the superoxide scavenging assay while weak inhibitory activity was observed against the enzyme xanthine oxidase. PMID:19912065

Karim, Aman; Noor, Atia Tun; Malik, Abdul; Qadir, Muhammad I; Choudhary, Muhammad I

2009-12-01

384

Phenolic glycosides from the stem bark of Caryocar villosum and C. glabrum.  

PubMed

Mushroom tyrosinase inhibitory activity of methanol extracts and polar fractions of the stem bark of Caryocar villosum and C. glabrum has been assessed. Seven new phenolic glycosides (1-7) were isolated from the most active fractions, along with 15 known compounds (8-22). The structures of these compounds were established on the basis of spectroscopic methods including 1D and 2D NMR analysis, HRESIMS, and comparison with literature experimental data for known compounds. PMID:18412393

Magid, Abdulmagid Alabdul; Voutquenne-Nazabadioko, Laurence; Harakat, Dominique; Moretti, Christian; Lavaud, Catherine

2008-05-01

385

The flavonoid glycosides of Cornus canadensis L. and its allies in Northwestern North America  

Microsoft Academic Search

Summary The flavonoid glycoside profile ofCornus canadensis L. and its allies in Northwestern North America has been determined; quercetin 3-O-glucoside, 3-O-galactoside, 3-O-sophoroside and 3-O-gentiobioside; kaempferol 3-O-glucoside and 3-O-arabinoside. The discontinuity in distribution pattern of quercetin 3-O-gentiobioside within these taxa, associated with the phytogeography and historical factors affecting plant distribution in this area, indicates a possible polytopic and polychronistic origin of

J. F. Bain; K. E. Denford

1979-01-01

386

Two new cucurbitane-type glycosides obtained from roots of Siraitia grosvenori SWINGLE.  

PubMed

Novel Cucurbitane-type glycosides, 5beta,19beta-epoxy-29-nor-3,11-dioxo-cucurbit-24-ene-27-oic acid 27-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1) and 19,29-nor-3,11-dioxo-cucurbit-4,24-diene-27-oic acid 27-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (2) were isolated from the roots of Siraitia grosvenori SWINGLE. PMID:19652416

Li, Dian-Peng; El-Aasr, Mona; Ikeda, Tsuyoshi; Ogata, Misato; Miyashita, Hiroyuki; Yoshimitsu, Hitoshi; Nohara, Toshihiro

2009-08-01

387

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

PubMed

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

Shabana, Samah; Kawai, Azusa; Kai, Kenji; Akiyama, Kohki; Hayashi, Hideo

2010-01-01

388

Mesophyll distribution of 'antioxidant' flavonoid glycosides in Ligustrum vulgare leaves under contrasting sunlight irradiance  

PubMed Central

Background and Aims Flavonoids have the potential to serve as antioxidants in addition to their function of UV screening in photoprotective mechanisms. However, flavonoids have long been reported to accumulate mostly in epidermal cells and surface organs in response to high sunlight. Therefore, how leaf flavonoids actually carry out their antioxidant functions is still a matter of debate. Here, the distribution of flavonoids with effective antioxidant properties, i.e. the orthodihydroxy B-ring-substituted quercetin and luteolin glycosides, was investigated in the mesophyll of Ligustrum vulgare leaves acclimated to contrasting sunlight irradiance. Methods In the first experiment, plants were grown at 20 % (shade) or 100% (sun) natural sunlight. Plants were exposed to 100 % sunlight irradiance in the presence or absence of UV wavelengths, in a second experiment. Fluorescence microspectroscopy and multispectral fluorescence microimaging were used in both cross sections and intact leaf pieces to visualize orthodihydroxy B-ring-substituted flavonoids at inter- and intracellular levels. Identification and quantification of individual hydroxycinnamates and flavonoid glycosides were performed via HPLC-DAD. Key Results Quercetin and luteolin derivatives accumulated to a great extent in both the epidermal and mesophyll cells in response to high sunlight. Tissue fluorescence signatures and leaf flavonoid concentrations were strongly related. Monohydroxyflavone glycosides, namely luteolin 4?-O-glucoside and two apigenin 7-O-glycosides were unresponsive to changes in sunlight irradiance. Quercetin and luteolin derivatives accumulated in the vacuoles of mesophyll cells in leaves growing under 100 % natural sunlight in the absence of UV wavelengths. Conclusions The above findings lead to the hypothesis that flavonoids play a key role in countering light-induced oxidative stress, and not only in avoiding the penetration of short solar wavelengths in the leaf.

Agati, Giovanni; Stefano, Giovanni; Biricolti, Stefano; Tattini, Massimiliano

2009-01-01

389

Small-intestinal transfer mechanism of prunasin, the primary metabolite of the cyanogenic glycoside amygdalin  

Microsoft Academic Search

1 The small-intestinal transfer of prunasin (D-mandelo nitrile-?-D-glucoside), the primary metabolite of amyg dalin which is not absorbed in the small intestine as such, was studied in rat jejunum and ileum in vitro.2 As shown by high pressure liquid chromatography, prunasin is transferred essentially intact across the intesti nal wall, without cleavage of the glycosidic bond and thus no formation

GJ Strugala; R. Stahl; B. Elsenhans; AG Rauws; W. Forth

1995-01-01

390

Alpha-agarases define a new family of glycoside hydrolases, distinct from beta-agarase families.  

PubMed

The gene encoding the alpha-agarase from "Alteromonas agarilytica" (proposed name) has been cloned and sequenced. The gene product (154 kDa) is unrelated to beta-agarases and instead belongs to a new family of glycoside hydrolases (GH96). The alpha-agarase also displays a complex modularity, with the presence of five thrombospondin type 3 repeats and three carbohydrate-binding modules. PMID:17513582

Flament, Didier; Barbeyron, Tristan; Jam, Murielle; Potin, Philippe; Czjzek, Mirjam; Kloareg, Bernard; Michel, Gurvan

2007-07-01

391

Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase  

Microsoft Academic Search

Lactase phlorizin hydrolase (LPH; EC 3.2.1.62) is a membrane-bound, family 1 ?-glycosidase found on the brush border of the mammalian small intestine. LPH, purified from sheep small intestine, was capable of hydrolysing a range of flavonol and isoflavone glycosides. The catalytic efficiency (kcat\\/Km) for the hydrolysis of quercetin-4?-glucoside, quercetin-3-glucoside, genistein-7-glucoside and daidzein-7-glucoside was 170, 137, 77 and 14 (mM?1 s?1)

Andrea J Day; Juan C D??az; Paul A Kroon; Russell Mclauchlan; Craig B Faulds; Geoff W Plumb; Michael R. A Morgan; Gary Williamson

2000-01-01

392

Sedative and anticonvulsant activities of goodyerin, a flavonol glycoside from Goodyera schlechtendaliana.  

PubMed

Goodyerin is a flavonol glycoside isolated from the whole plants of Goodyera schlechtendaliana which has been used as a substitute for the crude drug, Anoectochilus formosanus. The pharmacological properties of goodyerin were assayed for effects on spontaneous locomotor activity, on pentobarbital-induced hypnosis, and on anticonvulsant activity against picrotoxin-induced seizures in rodents. Goodyerin exhibited a significant and dose-dependent sedative and anticonvulsant effect. PMID:12164273

Du, Xiao-Ming; Sun, Ning-Yi; Takizawa, Nanako; Guo, Yong-Tian; Shoyama, Yukihiro

2002-05-01

393

Cornel Iridoid Glycoside Inhibits Inflammation and Apoptosis in Brains of Rats with Focal Cerebral Ischemia  

Microsoft Academic Search

The capacity of cornel iridoid glycoside (CIG) to suppress the manifestations of ischemic stroke was investigated. CIG was\\u000a administered to rats by the intragastric route once daily for 7 days. Focal cerebral ischemia was induced by 2 h of middle\\u000a cerebral artery occlusion followed by 24 h of reperfusion. In non-treated rats large infarct areas were observed within 24 h\\u000a of reperfusion. Examination of

Bai-liu YaChun-yang; Chun-yang Li; Lan Zhang; Wen Wang; Lin Li

2010-01-01

394

Glycosidic fraction of flue-cured tobacco leaves: its separation and component analysis.  

PubMed

The fraction containing glycosidic components was separated from flue-cured tobacco (Nicotiana tabacum L.) leaves by a facile method. Some components of the fraction were isolated and elucidated to be syringin, coniferin, cichoriin, benzyl-beta-D-glucoside, Blumenol A-beta-D-glucoside, and 5,6-epoxy-5,6-dihydro-3-hydroxy-beta-ionyl-beta-D-glucoside. Syringin and coniferin were detected in the Nicotiana species for the first time. PMID:10803957

Ito, K; Tanabe, Y; Kato, S; Yamamoto, T; Saito, A; Mori, M

2000-03-01

395

A new ellagic acid glycoside and DNA topoisomerase IB inhibitory activity of saponins from Putranjiva roxburghii.  

PubMed

Chemical investigation of the stem bark and leaves of Putranjiva roxburghii has resulted in the isolation of a new ellagic acid glycoside (5) along with four saponins (1-4). The structures of the isolated compounds were established by detailed spectral analysis. Incidentally putranoside-A methyl ester (4) has been isolated for the first time from this species and the saponins (1-4) exhibited potent DNA topoisomerase IB inhibitory activity. PMID:25026719

Kumar, Ashish; Chowdhury, Somenath Roy; Chakrabarti, Tulika; Majumdarb, Hemanta K; Jha, Tarun; Mukhopadhyay, Sibabrata

2014-05-01

396

Multifunctional, Biocompatible Supramolecular Hydrogelators Consist Only of Nucleobase, Amino Acid, and Glycoside  

PubMed Central

The integration of nucleobase, amino acid, and glycoside into a single molecule results in a novel class of supramolecular hydrogelators, which not only exhibit biocompatibility and biostability, but also facilitate the entry of nucleic acids into cytosol and nuclei of cells. This work illustrates a simple way to generate an unprecedented molecular architecture from the basic biological building blocks for the development of sophisticated soft nanomaterials, including supramolecular hydrogels.

Li, Xinming; Kuang, Yi; Shi, Junfeng; Gao, Yuan; Lin, Hsin-Chieh; Xu, Bing

2011-01-01

397

Lecythomycin, a new macrolactone glycoside from the endophytic fungus Lecythophora sp.  

PubMed

A new macrolactone glycoside, lecythomycin (1), 23-methyl-3-(1-O-mannosyl)-oxacyclotetracosan-1-one, was isolated from the endophytic fungus Lecythophora sp. (code 30.1), an endopyte of the Indonesian plant Alyxia reinwardtii. The structure of 1 was elucidated on the basis of NMR spectroscopic and mass spectrometric data. The isolated compound displayed antifungal activity against strains of Aspergillus fumigatus and Candida kruzei at minimal inhibitory concentrations (MIC) of 62.5-125 microg/mL. PMID:21615031

Sugijanto, Noor Erma; Diesel, Arnulf; Rateb, Mostafa; Pretsch, Alexander; Gogalic, Selma; Zaini, Noor Cholies; Ebel, Rainer; Indrayanto, Gunawan

2011-05-01

398

beta-Glucosidase inhibitory activities of phenylpropanoid glycosides, vanicoside A and B from Polygonum sachalinense rhizome.  

PubMed

The phenylpropanoid glycosides, vanicoside A and B, isolated from rhizomes of giant knotweed (Polygonum sachalinense) showed beta-glucosidase inhibitory activity, with IC(50) values of 59.8 and 48.3 mug/ml (59.9 and 50.5 muM), respectively. In contrast, p-coumaric acid and ferulic acid, corresponding to phenylpropanoyl moieties of vanicosides, exhibited very little inhibition. PMID:16828242

Kawai, Y; Kumagai, H; Kurihara, H; Yamazaki, K; Sawano, R; Inoue, N

2006-09-01

399

Validated high-performance thin-layer chromatography method for steviol glycosides in Stevia rebaudiana  

Microsoft Academic Search

A high-performance thin-layer chromatographic (HPTLC) method was developed and validated as per ICH (International Conferences on Harmonization) guidelines for simultaneous quantification of three steviol glycosides, i.e. steviolbioside, stevioside and rebaudioside-A in Stevia rebaudiana leaves. For achieving good separation, mobile phase of ethyl acetate–ethanol–water (80:20:12, v\\/v\\/v) on pre-coated silica gel 60 F254 HPTLC plates were used. The densitometric quantification of steviol

Vikas Jaitak; A. P. Gupta; V. K. Kaul; P. S. Ahuja

2008-01-01

400

Steviol Glycoside Content in Different Organs of Stevia rebaudiana and Its Dynamics during Ontogeny  

Microsoft Academic Search

The contents of three major steviol glycosides (SGs) (stevioside and rebaudiosides A and C) in vegetative and generative organs\\u000a during ontogeny of Stevia rebaudiana Bertoni were analysed with HPLC. Plant organs contained different amounts of the SGs, which declined in the following order:\\u000a leaves, flowers, stems, seeds, roots. The highest content of the SGs was found in upper young actively

N. I. Bondarev; M. A. Sukhanova; O. V. Reshetnyak; A. M. Nosov

2003-01-01

401

Kolokosides A-D: triterpenoid glycosides from a Hawaiian isolate of Xylaria sp.  

PubMed

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 absolute configuration of 1 was assigned by application of the exciton chirality method. Compound 1 exhibited activity against Gram-positive bacteria. PMID:17284074

Deyrup, Stephen T; Gloer, James B; O'Donnell, Kerry; Wicklow, Donald T

2007-03-01

402

Membrane receptor calorimetry: cardiac glycoside interaction with Na,K-ATPase  

Microsoft Academic Search

The receptor–ligand interaction between the cardiac glycoside Ouabain and purified, membrane-bound as well as micellar Na,K-ATPase is investigated. Calorimetric titrations are carried out with micromolar concentrations of the phosphorylated protein in the presence of Mg2+. The measured heat changes provide evidence for an exothermic, high affinity and specific receptor binding process as well as for a low affinity, nonspecific binding

E. Grell; E. Schick; E. Lewitzki

2001-01-01

403

Acid epimerization of 20-keto pregnane glycosides is determined by 2D-NMR spectroscopy  

Microsoft Academic Search

Carbohydrates influence many essential biological events such as apoptosis, differentiation, tumor metastasis, cancer, neurobiology,\\u000a immunology, development, host-pathogen interactions, diabetes, signal transduction, protein folding, and many other contexts.\\u000a We now report on the structure determination of pregnane glycosides isolated from the aerial parts of Ceropegia fusca Bolle (Asclepiadaceae). The observation of cicatrizant, vulnerary and cytostatic activities in some humans and animals

Víctor P. García

2011-01-01

404

A novel ?-xylosidase structure from Geobacillus thermoglucosidasius: the first crystal structure of a glycoside hydrolase family GH52 enzyme reveals unpredicted similarity to other glycoside hydrolase folds.  

PubMed

Geobacillus thermoglucosidasius is a thermophilic bacterium that is able to ferment both C6 and C5 sugars to produce ethanol. During growth on hemicellulose biomass, an intracellular ?-xylosidase catalyses the hydrolysis of xylo-oligosaccharides to the monosaccharide xylose, which can then enter the pathways of central metabolism. The gene encoding a G. thermoglucosidasius ?-xylosidase belonging to CAZy glycoside hydrolase family GH52 has been cloned and expressed in Escherichia coli. The recombinant enzyme has been characterized and a high-resolution (1.7?Ĺ) crystal structure has been determined, resulting in the first reported structure of a GH52 family member. A lower resolution (2.6?Ĺ) structure of the enzyme-substrate complex shows the positioning of the xylobiose substrate to be consistent with the proposed retaining mechanism of the family; additionally, the deep cleft of the active-site pocket, plus the proximity of the neighbouring subunit, afford an explanation for the lack of catalytic activity towards the polymer xylan. Whilst the fold of the G. thermoglucosidasius ?-xylosidase is completely different from xylosidases in other CAZy families, the enzyme surprisingly shares structural similarities with other glycoside hydrolases, despite having no more than 13% sequence identity. PMID:24816105

Espina, Giannina; Eley, Kirstin; Pompidor, Guillaume; Schneider, Thomas R; Crennell, Susan J; Danson, Michael J

2014-05-01

405

Semisynthesis of apigenin and acacetin-7-O-?-D-glycosides from naringin and their cytotoxic activities.  

PubMed

Apigenin-7-O-?-D-glycosides 1-8 and acacetin-7-O-?-D-glycosides 9-16 were semisynthesized from 4'-O-benzyl apigenin 17 and acacetin 18 by glycosidation and deprotection with the corresponding ?-acetylglycosyl bromide, respectively. Compounds 17 and 18 were prepared by iodination followed by base-induced elimination, 4'-O-benzylation, or 4'-O-methylation and acid hydrolysis using naringin as starting material which is readily available and cheap. Their cytotoxic potential against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) was evaluated by standard MTT method. The results show that compounds 2, 9, and 19 exhibit moderate cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480, while compound 3 exhibits potent cytotoxicity against MCF-7 selectively. Among the synthesized target compounds, 3, 4, 7, 11, 12, 15, and 16 were new compounds, the natural product 8 was the first synthesized and the synthesis of natural products 5, 6, 13, and 14 was efficiently improved by the new synthetic routes. PMID:22732304

Liu, Jidan; Chen, Ling; Cai, Shuanglian; Wang, Qiuan

2012-08-01

406

Inhibition of aldose reductase by phenylethanoid glycoside isolated from the seeds of Paulownia coreana.  

PubMed

Aldose reductase (AR) inhibitors have considerable therapeutic potential against diabetic complications and do not increase the risk of hypoglycemia. Through bioassay-guided fractionation of the 70% acetone extract obtained from Paulownia coreana seeds, phenylpropanoid glycosides (compounds 1-4) and 5 phenolic compounds were isolated (compounds 5-9). Their structures were determined on the basis of spectroscopic analysis and comparison with reported data. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against recombinant human aldose reductase (rhAR) and sorbitol formation in human erythrocytes. Phenylethanoid glycosides showed more effective than the phenolic compounds in inhibiting rhAR. Among the compounds, isocampneoside II (3) was found to significantly inhibit rhAR with an IC(50) value of 9.72 µM. In kinetic analyses performed using Lineweaver-Burk plots of 1/velocity and 1/concentration of substrate, isocampneoside II (3) showed uncompetitive inhibition against rhAR. Furthermore, it inhibited sorbitol formation in a rat lens incubated with a high concentration of glucose; this finding indicated that isocampneoside II (3) may effectively prevent osmotic stress in hyperglycemia. Thus, the P. coreana-derived phenylethanoid glycoside isocampneoside II (3) may have a potential therapeutics against diabetic complications. PMID:21212537

Kim, Jin Kyu; Lee, Yeon Sil; Kim, Seon Ha; Bae, Young Soo; Lim, Soon Sung

2011-01-01

407

[The detection of flavonoids glycosides from ginkgo biloba based on spectrofluorimetry].  

PubMed

Flavonoids glycosides from ginkgo are widely applied in pharmaceutical, food, daily necessities and other areas due to their variety of biological activities. To overcome the shortcoming of current methods of time wasting, complex operation and expensive costs, an accuracy, low costs and fast determination method was established for flavonoids glycosides from ginkgo. According to the principle that flavonoids can form fluorescent chelate with Al3+, the detection condition was explored with rutin as standard. The results showed that the fluorimetric intensy of chelate of rutin with Al3+ would be stabilized and achieve maximum with lambda(ex) = 400 nm and lambda(em) = 520 nm, in Al (NO3)3-(HAc-NaAc) reaction system for 1 500 s with pH 3.6. The linear regression equation y = 29.92x + 36.49 (R2 = 0.986) was deduced with the concentration of rutin and fluorescence intensy, and the linear range 1.8 x 10(-6) -3.2 x 10(-5) mol x L(-1). Flavonoids glycosides of cell suspension cultures from ginkgo biloba was detected by this method. The recovery experiments were also carried out with the average recovery rate of 101.3%. The advantages of high sensitivity, reproducibility, simple operation, and low costs were showed, indicating its good prospects. PMID:24555380

Shao, Ju-Fang; Wen, Zong-Zhuang; Zhu, Hong-Wei

2013-11-01

408

Anti-inflammatory activity of methyl salicylate glycosides isolated from Gaultheria yunnanensis (Franch.) Rehder.  

PubMed

Gaultheria yunnanensis (Franch.) Rehder is a kind of traditional Chinese herbal medicine used for the treatments of rheumatoid arthritis, swelling and pain. Two methyl salicylate glycosides, namely methyl benzoate-2-O-?-D-xylopyranosyl(1-6)-O-?-D-gluco-pyranoside (J12122) and methyl benzoate-2-O-?-D-xylopyranosyl(1-2)[O-?-D-xylopyranosyl(1-6)]-O-?-D-glucopyranoside (J12123), are natural salicylic derivatives isolated from Gaultheria yunnanensis. In this study, we investigated the anti-inflammatory activity of J12122 and J12123 on LPS-induced RAW264.7 macrophage cells by measuring the production of pro-inflammatory cytokines, accumulation of nitric oxide (NO), and level of reactive oxygen species (ROS). The results showed that both methyl salicylate glycosides dose-dependently inhibited the production of tumor necrosis factor-? (TNF-?), interleukin-1? (IL-1?), and IL-6, respectively. Consistent with these observations, J12122 and J12123 significantly suppressed the accumulation of NO, with an inhibitory rate of 56.20% and 51.72% at 3.0 ?g/mL concentration, respectively. Furthermore, the two methyl salicylate glycosides reduced the level of ROS induced by LPS. These results showed that the isolated compounds possess anti-inflammatory properties through inhibition the production pro-inflammatory cytokines, NO, and ROS. PMID:21555977

Zhang, Dan; Liu, Rui; Sun, Lan; Huang, Chao; Wang, Chao; Zhang, Dong-Ming; Zhang, Tian-Tai; Du, Guan-Hua

2011-01-01

409

A male gift to its partner? Cyanogenic glycosides in the spermatophore of longwing butterflies (Heliconius)  

NASA Astrophysics Data System (ADS)

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.

Cardoso, Márcio Zikán; Gilbert, Lawrence E.

2007-01-01

410

Suppression of positive inotropic and toxic effects of cardiac glycosides by amiloride.  

PubMed

Effects of amiloride on the inotropic and toxic actions of cardiac glycosides were examined using left atrial muscle isolated from guinea pig heart. Preincubation of atrial muscle with amiloride significantly decreased the maximum positive inotropic effect of dihydrodigoxin but failed to reduce that of isoproterenol. Amiloride prevented the contracture and significantly reduced the incidence of arrhythmias induced by 2 microM digoxin. Similar experiments examining 5 microM digoxin-induced arrhythmias showed that amiloride increased both the time required to produce arrhythmias and the fractional occupancy of sarcolemmal Na,K-ATPase by digoxin at the onset of arrhythmias. The antagonism of cardiac glycoside actions was best observed during the decline in developed tension elicited by amiloride subsequent to its initial positive inotropic effect. Amiloride had no effect on binding site concentration for ATP-dependent [3H]ouabain binding but decreased affinity of the binding sites for ouabain in membrane preparations obtained from guinea pig heart. Furthermore, amiloride inhibited Na,K-ATPase activity and increased the IC50 value for ouabain inhibition of the enzyme. These results indicate that amiloride antagonizes the positive inotropic and toxic effects of cardiac glycosides. Possible mechanisms for the antagonism include inhibition of sarcolemmal Na+/Ca2+ or Na+/H+ exchange. PMID:2998821

Kennedy, R H; Akera, T; Brody, T M

1985-09-24

411

Structure and Biological Evaluation of Novel Cytotoxic Sterol Glycosides from the Marine Red Alga Peyssonnelia sp.  

PubMed Central

Bioactivity-guided fractionation of the extract from a Fijian red alga Peyssonnelia sp. led to the isolation of two novel sterol glycosides 19-O-?-d-glucopyranosyl-19-hydroxy-cholest-4-en-3-one (1) and 19-O-?-d-N-acetyl-2-aminoglucopyranosyl-19-hydroxy-cholest-4-en-3-one (2), and two known alkaloids indole-3-carboxaldehyde (3) and 3-(hydroxyacetyl)indole (4). Their structures were characterized by 1D and 2D NMR and mass spectral analysis. The sterol glycosides inhibited cancer cell growth with mean IC50 values (for 11 human cancer cell lines) of 1.63 and 1.41 µM for 1 and 2, respectively. The most sensitive cancer cell lines were MDA-MB-468 (breast) and A549 (lung), with IC50s in of 0.71–0.97 µM for 1 and 2. Modification of the sterol glycoside structures revealed that the ?,?-unsaturated ketone at C-3 and oxygenation at C-19 of 1 and 2 are crucial for anticancer activity, whereas the glucosidic group was not essential but contributed to enhanced activity against the most sensitive cell lines.

Lin, An-Shen; Engel, Sebastian; Smith, Benjamin A.; Fairchild, Craig R.; Aalbersberg, William; Hay, Mark E.; Kubanek, Julia

2010-01-01

412

Variegatusides: New Non-Sulphated Triterpene Glycosides from the Sea Cucumber Stichopus variegates Semper  

PubMed Central

Four new triterpene glycosides, variegatusides C–F (1–4), together with three structurally known triterpene glycosides, variegatusides A and B (5, 6), and holothurin B (7), were isolated from the sea cucumber Stichopus variegates Semper (Holothuriidae), collected from the South China Sea. Their structures were elucidated on the basis of extensive spectral analysis (nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS)) and chemical evidence. Variegatusides C–F exhibit the same structural feature consisting of the presence of a 23-hydroxyl group at the holostane-type triterpene aglycone side chain. Variegatuside C (1) has a double bond (24, 25) in this same chain, while variegatuside D (2) exhibits a 8(9)-ene bond in the holostane-type triterpene aglycone, which has not been extracted from other sea cucumber species. Compound 4 is a native compound from the sea cucumber S. variegates Semper, which has been reported to be desacetylstichloroside B1. Except for holothurin B, these glycosides have no sulfate group in their sugar chain and show potent antifungal activities in vitro biotests.

Wang, Xiao-Hua; Zou, Zheng-Rong; Yi, Yang-Hua; Han, Hua; Li, Ling; Pan, Min-Xiang

2014-01-01

413

NF-?B inhibitory activities of glycosides and alkaloids from Zanthoxylum schinifolium stems.  

PubMed

Zanthoxylum schinifolium is an aromatic shrub, the pericarp and leaves of which are widely used in culinary applications in East Asian countries. In the present study, one new neolignan glycoside, zanthoxyloside A (1) together with 16 known glycosides (2-12) and alkaloids (13-17), were isolated from methanol extract of the stems of Z. schinifolium. The absolute configuration of one known monoterpenoid glycoside (2) was determined. The structures of the isolated compounds were established by one dimensional (1D), 2D NMR and mass spectrometry. The nuclear factor-?B (NF-?B) inhibitory activities of the isolated compounds stimulated with tumor necrosis factor alpha (TNF?) were measured using a luciferase reporter system. Compounds 1, 5, 16, and 17 exhibited significant inhibition of NF-?B activation in a dose-dependent manner. Furthermore, compounds 1, 5, 16, and 17 inhibited TNF?-induced expression of inducible nitric oxide synthase (iNOS) and intercellular adhesion molecule-1 (ICAM-1) mRNA and dose-dependent inhibition of iNOS promoter activity. PMID:24492590

Li, Wei; Yang, Seo Young; Yan, Xi Tao; Sun, Ya Nan; Song, Seok Bean; Kang, Hee Kyoung; Kim, Young Ho

2014-01-01

414

Regioselectivity of enzymatic glycosylation of 6-O-acyl glycosides in supersaturated solutions.  

PubMed

The regioselectivity of enzymatic transglycosylation of 6-O-acetyl glycosides in supersaturated solutions was investigated using a range of commercially available enzymes, Escherichia coli, barley, and Kluyveromyces spp. beta-galactosidase, green coffee bean alpha-galactosidase, jack bean alpha-mannosidase, rice alpha-glucosidase, and almond beta-glucosidase. It has been shown that 6-O-acetyl glycosides serve as good substrates for these enzymes, which, under the reaction conditions, are "forced" to transfer monosaccharide units to the secondary hydroxyl groups of the acceptors. In a variety of transglycosylations studied the (1-3)-linked disaccharide products were the predominant regioisomers isolated. The selectivity of the reaction varied significantly depending on the acceptor glycosides and the enzyme used. Exquisite specificity was observed in some cases, but in others approximately equal quantities of two disaccharides products were isolated. In the best transfers the yield approached 30%. The methodology described offers a quick and facile route to disaccharides that may be difficult and/or time consuming to make by conventional chemical synthesis. PMID:10918132

MacManus, D A; Vulfson, E N

2000-09-20

415

Zebrafish chemical screening reveals the impairment of dopaminergic neuronal survival by cardiac glycosides.  

PubMed

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 ?3 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

Sun, Yaping; Dong, Zhiqiang; Khodabakhsh, Hadie; Chatterjee, Sandip; Guo, Su

2012-01-01

416

Zebrafish Chemical Screening Reveals the Impairment of Dopaminergic Neuronal Survival by Cardiac Glycosides  

PubMed Central

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 ?3 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.

Sun, Yaping; Dong, Zhiqiang; Khodabakhsh, Hadie; Chatterjee, Sandip; Guo, Su

2012-01-01

417

Stability of N-glycosidic bond of (5?S)-8,5?-cyclo-2?-deoxyguanosine  

PubMed Central

8,5?-Cyclopurine deoxynucleosides are unique tandem lesions containing an additional covalent bond between the base and the sugar. These mutagenic and genotoxic lesions are repaired only by nucleotide excision repair. The N-glycosidic (or C1?-N9) bond of 2?-deoxyguanosine (dG) derivatives is usually susceptible to acid hydrolysis, but even after cleavage of this bond of the cyclopurine lesions, the base would remain attached to the sugar. Here, the stability of the N-glycosidic bond and the products formed by formic acid hydrolysis of (5?S)-8,5?-cyclo-2?-deoxyguanosine (S-cdG) were investigated. For comparison, the stability of the N-glycosidic bond of 8,5?-cyclo-2?,5?-dideoxyguanosine (ddcdG), 8-methyl-2?-deoxyguanosine (8-Me-dG), 7,8-dihydro-8-oxo-2?-deoxyguanosine (8-Oxo-dG), and dG was also studied. In various acid conditions, S-cdG and ddcdG exhibited similar stability to hydrolysis. Likewise, 8-Me-dG and dG showed comparable stability, but the half lives of the cyclic dG lesions were at least 5-fold higher than dG or 8-Me-dG. NMR studies were carried out to investigate the products formed after the cleavage of the C1?-N9 bond. 2-Deoxyribose generated ? and ? anomers of deoxyribopyranose and deoxyribopyranose oligomers following acid treatment. S-cdG gave ? and ? deoxyribopyranose linked guanine as the major products, but ? and ? anomers of deoxyribofuranose linked guanine and other products were also detected. The N-glycosidic bond of 8-Oxo-dG was found exceptionally stable in acid. Computational studies determined that both the protonation of the N7 atom and the rate constant in the bond breaking step control the overall kinetics of hydrolysis, but both varied for the molecules studied indicating a delicate balance between the two steps. Nevertheless, the computational approach successfully predicted the trend observed experimentally. For 8-Oxo-dG, the low pKa of O8 and N3 prevented appreciable protonation, making the free energy for N-glycosidic bond cleavage in the subsequent step very high.

Das, Rajat S.; Samaraweera, Milinda; Morton, Martha; Gascon, Jose A.; Basu, Ashis K.

2012-01-01

418

Steroidal glycosides from Veronica chamaedrys L. Part I. The structures of chamaedrosides C, C1, C2, E, E1 and E2.  

PubMed

Two new spirostane glycosides, chamaedrosides C (1) and C1 (2), two new furostane glycosides, chamaedrosides E (4) and E1 (5), and two new furospirostane glycosides, chamaedrosides C2 (3) and E2 (6), have been isolated from Veronica chamaedrys L. plants. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D- and 2D-NMR experiments, as well as MS analysis. The given compounds have been found for the first time. PMID:22799076

Marchenko, Alexandra; Kintya, Pavel; Wyrzykiewicz, Bozena; Gorincioi, Elena

2012-05-01

419

Synthetic Studies on Sialoglycoconjugates 9: An Efficient Method for the Selective Acetolysis of 2-(Trimethylsilyl)Ethyl Glycosides Using Ferric Chloride in Acetic Anhydride  

Microsoft Academic Search

After the first report of the synthesis and deblocking of some 2-(trimethylsilyl)ethyl (SE) glycosides by Lipshutz and coworkers, a few more papers appeared describing facile deprotection of the SE group in such glycosides or some of their derivatives. We have employed the SE glycosides of D-galactose, D-glucose, D-galacto-samine, D-glucosamine, D-lactose, and neuraminic acid very extensively in our work on oligosaccharide

K. P. R. Kartha; Makoto Kiso; Akira Hasegawa

1989-01-01

420

Reversible optical computing circuits.  

PubMed

Planar optical implementations of binary adders are developed using a three-port nonlinear interface device as the single computing primitive. The device is bit-conserving and both optically and logically reversible. PMID:19741792

Cuykendall, R; Andersen, D R

1987-07-01

421

Reverse Flow Personal Ventilation.  

National Technical Information Service (NTIS)

The potential contribution of reverse flow personal ventilation for the relief of thermal stress in the aviation field is reviewed. Current evidence is discussed and recommendations are made for further research. (Author)

D. G. Robertson J. Morrison J. R. Allan

1971-01-01

422

Reversing the arms race  

SciTech Connect

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.

von Hippel, F. (Princeton Univ., NJ (United States)); Sagdeev, R.Z. (Space Research Inst., Moscow (USSR))

1992-01-01

423

Reversibility of antibiotic resistance.  

PubMed

Abstract 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

Sundqvist, Martin

2014-05-01

424

Tektites and Geomagnetic Reversals  

Microsoft Academic Search

THE microscopic glassy objects which occur in sediments deposited in the Australasian area during and shortly after the last magnetic polarity reversal are apparently tektites (see succeeding communication). The last reversal occurred 0.7 × 106 yr ago: potassium-argon dates1 indicate that the Australasian tektites were formed 0.7 × 106 yr ago. The tektites were formed and deposited at the same

Bill Glass; Bruce C. Heezen

1967-01-01

425

Reversibility of antibiotic resistance  

PubMed Central

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.

2014-01-01

426

Image reversal revisited  

Microsoft Academic Search

Image reversal methods can be useful in those cases, where a resist of a specific tone is lacking particular desirable properties, e.g. etch resistance. Reversal of the image, e-beam written in Hydrogen SilsesQuioxane (HSQ), by a proper ‘work around’ method may result in a positive tone high resolution process with a high etch resistance, which is lacking in PMMA. HSQ

F. C. M. J. M. van Delft; F. J. H. van der Kruis; H. H. A. J. Roosen; H. W. J. J. van de Laar

2008-01-01

427

On thermodynamic and microscopic reversibility  

SciTech Connect

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.

Crooks, Gavin E.

2011-07-12

428

Induction of phenolic glycosides by quaking aspen (Populus tremuloides) leaves in relation to extrafloral nectaries and epidermal leaf mining.  

PubMed

We studied the effect of epidermal leaf mining on the leaf chemistry of quaking aspen, Populus tremuloides, during an outbreak of the aspen leaf miner, Phyllocnistis populiella, in the boreal forest of interior Alaska. Phyllocnistis populiella feeds on the epidermal cells of P. tremuloides leaves. Eleven days after the onset of leaf mining, concentrations of the phenolic glycosides tremulacin and salicortin were significantly higher in aspen leaves that had received natural levels of leaf mining than in leaves sprayed with insecticide to reduce mining damage. In a second experiment, we examined the time course of induction in more detail. The levels of foliar phenolic glycosides in naturally mined ramets increased relative to the levels in insecticide-treated ramets on the ninth day following the onset of leaf mining. Induction occurred while some leaf miner larvae were still feeding and when leaves had sustained mining over 5% of the leaf surface. Leaves with extrafloral nectaries (EFNs) had significantly higher constitutive and induced levels of phenolic glycosides than leaves lacking EFNs, but there was no difference in the ability of leaves with and without EFNs to induce phenolic glycosides in response to mining. Previous work showed that the extent of leaf mining damage was negatively related to the total foliar phenolic glycoside concentration, suggesting that phenolic glycosides deter or reduce mining damage. The results presented here demonstrate that induction of phenolic glycosides can be triggered by relatively small amounts of mining damage confined to the epidermal tissue, and that these changes in leaf chemistry occur while a subset of leaf miners are still feeding within the leaf. PMID:20354896

Young, Brian; Wagner, Diane; Doak, Patricia; Clausen, Thomas

2010-04-01

429

Molluscicidal activity of cardiac glycosides from Nerium indicum against Pomacea canaliculata and its implications for the mechanisms of toxicity.  

PubMed

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

Dai, Lingpeng; Wang, Wanxian; Dong, Xinjiao; Hu, Renyong; Nan, Xuyang

2011-09-01

430

Reversible collisionless magnetic reconnection  

SciTech Connect

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.

Ishizawa, A.; Watanabe, T.-H. [National Institute for Fusion Science, Toki 509-5292 (Japan)] [National Institute for Fusion Science, Toki 509-5292 (Japan)

2013-10-15

431

Reversible adaptive trees.  

PubMed

We describe reversible adaptive trees, a class of stochastic algorithms modified from the formerly described adaptive trees. They evolve in time a finite subset of an ambient Euclidean space of any dimension, starting from a seed point and, accreting points to the evolving set, they grow branches towards a target set which can depend on time. In contrast with plain adaptive trees, which were formerly proven to have strong convergence properties to a static target, the points of reversible adaptive trees are removed from the tree when they have not been used recently enough in a path from the root to an accreted point. This, together with a straightening process performed on the branches, permits the tree to follow some moving targets and still remain adapted to it. We then discuss in what way one can see such reversible trees as a model for a qualitative property of resilience, which leads us to discuss qualitative modeling. PMID:23934230

Kergosien, Yannick L

2013-09-01

432

Synthesis of a serine-based neuraminic acid C-glycoside.  

PubMed

Cell-surface carbohydrates are classified by the nature of their linkages to the protein as either N-linked or O-linked. O- and N-glycans are involved in a number of important biological functions. These activities can be lost on glycoprotein catabolism when these glycan linkages are enzymatically hydrolyzed. The design and synthesis of novel C-linked glycans should provide catabolically stable glycoproteins useful for understanding and regulating important biological processes. Our efforts are currently directed toward the synthesis of C-glycosides of ulosonic acids. This paper describes the first synthesis of a serine-based neuraminic acid C-glycoside. The protecting group chemistry required for both carbohydrate and peptide syntheses complicates this approach. Different protecting group strategies were investigated for use in the samarium diiodide mediated C-glycosylation reaction. The key elements of our synthetic approach involve the following: (i) the substitution of homoserine for serine in the C-glycosylation reaction to introduce a carbon in place of the O-glycosidic oxygen, (ii) the use of benzyloxycarbonyl as a homoserine protecting group, compatible with samarium diiodide mediated C-glycosylation reaction, and (iii) the reduction of the carbonyl group in homoserine early in the synthesis to improve C-glycosylation yield and to avoid lactone formation. Using this combined approach, we prepared 4-O-acetyl-4-[2-C-(1-methyl 5-acetamido 4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-d-erythro-l-manno-nononate)]-2S-(benzyloxycarbonyl)amino-1-carboxylic acid (1), which will be used in peptide synthesis to prepare glycopeptides containing catabolically stable C-linked neuraminic acid. PMID:12662036

Wang, Qun; Linhardt, Robert J

2003-04-01

433

Identification, quantification and antioxidant activity of acylated flavonol glycosides from sea buckthorn (Hippophae rhamnoides ssp. sinensis).  

PubMed

A novel acylated flavonol glycoside: isorhamnetin (3-O-[(6-O-E-sinapoyl)-?-D-glucopyranosyl-(1?2)]-?-D-glucopyranosyl-7-O-?-L-rhamnopyranoside) (1), together with two known acylated flavonol glycosides: quercetin (3-O-[(6-O-E-sinapoyl)-?-D-glucopyranosyl-(1?2)]-?-D-glucopyranosyl-7-O-?-L-rhamnopyranoside) (2) and kaempferol (3-O-[(6-O-E-sinapoyl)-?-D-glucopyranosyl-(1?2)]-?-D-glucopyranosyl-7-O-?-L-rhamnopyranoside) (3) were isolated from the n-butanol fraction of sea buckthorn (Hippophae rhamnoides ssp. sinensis) berries for the first time by chromatographic methods, and their structures were elucidated using UV, MS, (1)H and (13)C NMR, and 2D NMR. Compounds 1-3 showed good scavenging activities, with respective IC50 values of 8.91, 4.26 and 30.90 ?M toward the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical; respective Trolox equivalent antioxidant capacities of 2.89, 4.04 and 2.44 ?M ?M(-1) toward 2,2'-azino-bis-3-ethyl-benzothiazoline-6-sulphonate (ABTS) radical. The quantitative analysis of the isolated acylated flavonol glycosides was performed by HPLC-DAD method. The contents of compounds 1-3 were in the range of 12.2-31.4, 4.0-25.3, 7.5-59.7 mg/100 g dried berries and 9.1-34.5, 75.1-182.1, 29.2-113.4 mg/100 g dried leaves, respectively. PMID:23870862

Chen, Chu; Xu, Xue-Min; Chen, Yang; Yu, Meng-Yao; Wen, Fei-Yan; Zhang, Hao

2013-12-01

434

[Peripheral blood cell factors of Graves ophthalmopathy and effect of intervention with tripterygium glycosides].  

PubMed

To explore the effect of tripterygium glycosides on the level of peripheral blood cell factors of Graves ophthalmopathy (GO). In the study, 64 patients of GO in moderate-severe acute stage were selected, and randomly divided into the treatment group (32 cases) and the control group (32 cases). Both of the two groups were provided with basic treatment. The control group was added with prednisone(0. 75 mg kg-1 d-1 ), which gradually reduced (by 5-10 mg week-1 )to the minimum dose of 5 mg d-1. The treatment group was treated with 20 mg tripterygium glycosides, three times a day. One therapy course is three months. The levels of peripheral blood cells(TNF-alpha , IL-2, IL-10, IFN-gamma)of the two groups before and after the treatment and the clinical efficacy were observed. The study indicated that, before the treatment, TNF-alpha, IL-2, IFN-gamma in both groups were significantly higher than that in the health group, but with IL-10 notably lower than the healthy group. After the treatment, TNF-a, IL-2, IFN-gamma in the treatment group significantly decreased, but with IL-10 significantly increasing (P <0. 01). After the treatment, the two groups showed significant difference (P <0. 01). The total clinical efficacy in the treatment group was 88. 10% , and that in the control group was 57. 14% (P <0. 01). After the treatment, the two groups showed significant changes in the exophthalmos degree (P < 0. 01). The results showed that the level of peripheral blood cells (TNF-alpha,IL-2, IL-10, IFN-gamma)of GO patients was positively correlated with the severity of ocular disease. The combined therapy of tripterygium glycosides and methimazole show such advantages as low side effect and high clin- PMID:24946565

Xu, Jian-Ping; Xu, Jian-Ping; Xu, Chen; Chen, Jun; Jin, Zhi-Hua; Zheng, Hong-Fei; Zhu, Jun

2014-02-01

435

The role of water in the design of glycosidic linkage flexibility  

NASA Astrophysics Data System (ADS)

In this paper we show how a variety of computational methods are used to understand the role that water plays in the solution conformational dynamics of carbohydrates. A comparison is made between maltose and a designed disaccharide (?-D-Glc-NAc-(1?4)-?-D-Glc-3-NH2) in which the cross glycosidic linkage hydrogen bonds have been significantly strengthened. However, despite the stronger intramolecular hydrogen bonds in the maltose derivative, the correlation times for glycosidic dihedral angle fluctuations are approximately the same for the two sugars. Upon investigation of the water in the first hydration shells for the two disaccharides, high water probability densities were found between the functional groups straddling the glycosidic linkage that bonds the two monosaccharides together. This probability density corresponds to single water molecules forming bridging hydrogen bonds between the functional groups on either side of the linkage for periods of 3.66 ps in the case of maltose and 8.36 ps in the case of the amine derivative. Ab initio studies of saccharide structure interaction with single water molecules reveal that these intermolecular (sugar-solvent) hydrogen bonds are of similar strength to the intramolecular (sugar-sugar) hydrogen bonds. This combination of molecular dynamics and ab initio computational methods demonstrates that increasing the internal hydrogen bond strength in oligosaccharides does not lead to significantly slower internal molecular motion of these sugars in solution. The intermolecular hydrogen bonds formed with water compete equally with the intramolecular hydrogen bonds in the sugar. This result has important implications when considering hydrophobic versus hydrophilic effects in glycoproteins.

Naidoo, Kevin J.; Yu-Jen Chen, Jeff

436

Habit reversal in the crab  

Microsoft Academic Search

Bermuda land crabs, Gecarcinus lateralis, were trained in a 2-choice spatial situation with escape from water as reinforcement. For one group the positive and negative alternatives were reversed every 4 days for 9 reversals; the remainder of the Ss had 35 days of constant conditions, followed by 13 daily reversals. Adjustment to reversal was rapid to begin with, but \\

Lois-Ellin G. Datta; Sandra Milstein; M. E. Bitterman

1960-01-01

437

The Causes of Preference Reversal  

Microsoft Academic Search

Observed preference reversal cannot be adequately explained by violations of independence, the reduction axiom, or transitivity. The primary cause of preference reversal is the failure of procedure invariance, especially the overpricing of low-probability, high-payoff bets. This result violates regret theory and generalized (nonindependent) utility models. Preference reversal and a new reversal involving time preferences are explained by scale compatibility, which

Amos Tversky; Paul Slovic; Daniel Kahneman

1990-01-01

438

Sequential Polarity-Reversing Circuit  

NASA Technical Reports Server (NTRS)

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.

Labaw, Clayton C.

1994-01-01

439

Three new phenolic glycosides from the Tibetan medicinal plant Aconitum tanguticum.  

PubMed

Three new phenolic glycosides, such as (Z)-sinapic acid-4-O-?-d-allopyranoside (1), 3,4-dihydroxyphenethoxy-8-O-?-d-[6-O-(4-O-?-d-glucopyranosyl)-feruloyl]-glucopyranoside (2), and 4-dihydroxyphenethoxy-8-O-?-d-[6-O-(4-O-?-d-glucopyranosyl)-feruloyl]-glucopyranoside (3) were isolated from the EtOH extract of whole plant of Aconitum tanguticum (Maxim.) Stapf. The structures of the new compounds were elucidated by spectroscopic methods, and the total (1)H NMR and (13)C NMR chemical shifts were assigned. PMID:23768043

Xu, Lu; Luo, Ming; Lin, Li-Me; Zhang, Xiao; Li, Chun; Wang, Zhi-Min; Luo, Yong-Ming

2013-07-01

440

Effect of Morinda citrifolia fruit extract and its iridoid glycosides on blood fluidity.  

PubMed

The aim of this study was to investigate the effect of Morinda citrifolia fruit on blood fluidity. M. citrifolia fruit extract (MCF-ext) was investigated for its influence on blood aggregation and fibrinolysis. MCF-ext inhibited polybrene-induced erythrocyte aggregation and thrombin activity. The fibrinolytic activity of MCF-ext, in the euglobulin lysis time test and fibrin plate assay, is reported here for the first time. One of the active compounds was an iridoid glycoside, asperulosidic acid. The results indicated that MCF-ext is a potentially useful health food which is capable of improving blood flow and preventing lifestyle-related diseases. PMID:24604344

Murata, Kazuya; Abe, Yumi; Futamura-Masuda, Megumi; Uwaya, Akemi; Isami, Fumiyuki; Deng, Shixin; Matsuda, Hideaki

2014-07-01

441

A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.  

PubMed Central

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 1–3 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.

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

442

Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists.  

PubMed

A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4N, -4C, -7, -8N, -9N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8N, and 9N with up to 40-fold affinity enhancements relative to methyl ?-d-galactopyranoside due to the coumarylmethyl moieties. PMID:24973029

Rajput, Vishal Kumar; Leffler, Hakon; Nilsson, Ulf J; Mukhopadhyay, Balaram

2014-08-01

443

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

PubMed

Snow hebes are the alpine cushion-forming plants of New Zealand Veronica, formerly classified as Chionohebe. The chemical compositions of Veronica pulvinaris and Veronica thomsonii were studied and 33 water-soluble compounds were isolated. The structures of 14 previously unknown esters of phenylethanoid glycosides were elucidated by spectroscopic analyses. Further, eight known phenylethanoids, nine iridoids, 6'-feruloyl-sucrose and mannitol are also reported. It was found that the iridoid profile of the snow hebes was different from the other species of Veronica in New Zealand but similar to the alpine Northern Hemisphere representatives of the genus. PMID:20460800

Taskova, Rilka M; Kokubun, Tetsuo; Ryan, Ken G; Garnock-Jones, Phil John; Jensen, Soren Rosendal

2010-05-01

444

Search for "in vitro" antiviral activity of a new isoflavonic glycoside from Ulex europaeus.  

PubMed

Extracts from Ulex europaeus L. (Fabaceae) were tested for antiviral activity against HSV-1 and poliovirus. It was found that the n-butanolic extract significantly inhibited the replication of these viruses, as shown by inhibition of cytophathic effects and reduction of plaques; the extract has neither a prophylactic nor a virucidal activity. From this extract has been isolated and identified by chromatographic, chemical, and spectroscopic methods, the 5-O-methylgenistein 7-O-beta D-glucopyranoside. This isoflavonic glycoside has not been previously described and it is responsible at least partially for the antiviral activity. PMID:2162546

De Rodriguez, D J; Chulia, J; Simőes, C M; Amoros, M; Mariotte, A M; Girre, L

1990-02-01

445

DOSY NMR applied to analysis of flavonoid glycosides from Bidens sulphurea.  

PubMed

2D DOSY 1H NMR has proved to be a useful technique in the identification of the molecular skeleton of the four major compounds of ethyl acetate extract of aerial parts of Bidens sulphurea (Asteraceae). The combination of this technique with HPLC, mass spectrometry and other NMR techniques enabled the identification of four flavonoid glycosides: quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-beta-D-glycopyranoside, quercetin-3-O-alpha-L-arabinofuranoside and quercetin-3-O-beta-D-rhamnopyranoside. PMID:19768723

Rodrigues, Edilene Delphino; da Silva, Denise Brentan; de Oliveira, Dionéia Camilo Rodrigues; da Silva, Gil Valdo José

2009-12-01

446

Shamiminol: a new aromatic glycoside from the stem bark of Bombax ceiba.  

PubMed

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

Faizi, Shaheen; Zikr-Ur-Rehman, Sadia; Versiani, Muhammad Ali

2011-12-01

447

Biosynthesis of coumarin glycosides by transgenic hairy roots of Polygonum multiflorum.  

PubMed

To investigate the substrate specificity and regio-selectivity of coumarin glycosyltransferases in transgenic hairy roots of Polygonum multiflorum, esculetin (1) and eight hydroxycoumarins (2-9) were employed as substrates. Nine corresponding glycosides (10-18) involving four new compounds, 6-chloro-4-methylcoumarin 7-O-?-D-glucopyranoside (15), 6-chloro-4-phenylcoumarin 7-O-?-D-glucopyranoside (16), 8-hydroxy-4-methylcoumarin 7-O-?-D-glucopyranoside (17), and 8-allyl-4-methylcoumarin 7-O-?-D-glucopyranoside (18), were biosynthesized by the hairy roots. PMID:22738975

Zhou, Liangbin; Tian, Tian; Xue, Bailin; Song, Liyan; Liu, Ling; Yu, Rongmin

2012-01-01

448

Chemoenzymatic synthesis of two new halogenated coumarin glycosides as potential antifungal agents.  

PubMed

Two new potential antifungal coumarin glycosides, 6-chlorocoumarin 7-O-beta-D-glucopyranoside (1) and 7-hydroxy-4-trifluoromethyl-coumarin 5-O-beta-D-glucopyranoside (2), were synthesized via enzyme-mediated glycosylation of the respective aglycone, 6-chloro-7-hydroxycoumarin and 5,7-dihydroxy-4-trifluoromethylcoumarin, using transgenic hairy roots of Polygonum multiflorum. Instead of application of the isolated enzyme and exogenous sugar donors, hairy roots of P. multiflorum were successfully adapted as a whole-cell biocatalyst. PMID:23157002

Zhou, Liangbin; Liu, Ling; Tian, Tian; Xue, Bailin; Yu, Rongmin

2012-10-01

449

Triglyceride accumulation inhibitory effects of phenylpropanoid glycosides from Boschniakia rossica Fedtsch et Flerov.  

PubMed

Bioassay-guided fractionation led to isolation of five new phenylpropanol glycosides, rossicasides G (1), H (2), I (3), J (4), and K (5), together with seven known compounds (6-12) from Boschniakia rossica. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, HRESI-TOF-MS, 1D and 2D NMR). Activity screening results showed that some isolates had TG accumulation inhibitory effects in HepG2 cells. Furthermore, the structure-activity relationship was partly clarified. PMID:23313269

Zhang, Yi; Wu, Chunhua; Guo, Lingling; Chen, Yue; Han, Lifeng; Liu, Erwei; Gao, Xiumei; Wang, Tao

2013-03-01

450

Three new glycosides from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO.  

PubMed

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

Kikuchi, Masao; Kakuda, Rie; Kikuchi, Masafumi; Yaoita, Yasunori

2008-04-01

451

Acyl glycosides lignans, coumarins, and terpenes from the stems of Erycibe obtusifolia.  

PubMed

Nine new acyl glycosides, obtusifosides A-I (1-9), and eight known compounds have been isolated from an EtOH extract of the stems of Erycibe obtusifolia. Their structures were elucidated on the basis of a spectroscopic data analysis (NMR, HRESIMS, and CD) and chemical evidence. The hepatoprotective effects of some of the compounds from d-galactosamine-induced cytotoxicity in HL-7702 hepatic cells were evaluated. Compounds 1, 10, 11, 13, 16, and 17 showed significant hepatoprotective activities compared with the positive control bicyclol at concentrations of 1×10(-5)M. PMID:23524110

Liu, Zhao-Zhen; Zhan, Zhi-Lai; Liu, Fu; Yang, Ya-Nan; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

2013-05-01

452

Coastally Trapped Wind Reversals  

NSDL National Science Digital Library

This module provides a brief overview of Coastally Trapped Wind Reversals. This module starts with a forecast scenario that occurs along the California coast. The module then proceeds to describe the structure and climatology of these disturbances, as well as their synoptic and mesoscale evolution. The instruction concludes with a section on forecasting coastally trapped wind reversals. The module also includes a concise summary for quick reference and a final exam to test your knowledge. Like other modules in the Mesoscale Meteorology Primer, this module comes with audio narration, rich graphics, and a companion print version.

Spangler, Tim

2002-07-01

453

Reverse shoulder arthroplasty.  

PubMed

The reverse shoulder arthroplasty is considered to be one of the most significant technological advancements in shoulder reconstructive surgery over the past 30 years. It is able to successfully decrease pain and improve function for patients with rotator cuff-deficient shoulders. The glenoid is transformed into a sphere that articulates with a humeral socket. The current reverse prosthesis shifts the center of rotation more medial and distal, improving the deltoid's mechanical advantage. This design has resulted in successful improvement in both active shoulder elevation and in quality of life. PMID:23827841

Jarrett, Claudius D; Brown, Brandon T; Schmidt, Christopher C

2013-07-01

454

Regioselective synthesis of p-nitrophenyl glycosides of ?- d-galactopyranosyl-disaccharides by transglycosylation with ?- d-galactosidases  

Microsoft Academic Search

The ?-d-galactosidase from porcine liver induced regiospecific transglycosylation of ?-d-galactose from ?-d-Gal-OC6H4NO2-o to OH-6 of, respectively, p-nitrophenyl glycoside acceptors of Gal, GlcNAc and GalNAc to afford ?-Gal-(1?6)-?-Gal-OC6H4NO2-p, ?-Gal-(1?6)-?-Gal-OC6H4NO2-p, ?-Gal-(1?6)-?-GalNAc-OC6H4NO2-p, ?-Gal-(1?6)-?-GalNAc-OC6H4NO2-p, ?-Gal-(1?6)-?-GlcNAc-OC6H4NO2-p, and ?-Gal-(1?6)-?-GlcNAc-OC6H4NO2-p. The enzyme showed much higher transglycosylation activity for the ?-glycoside acceptors than the corresponding ?-glycoside acceptors. The regioselectivity of the ?-d-galactosidase from Bacilluscirculans ATCC 31382 greatly depended

Xiaoxiong Zeng; Rika Yoshino; Takeomi Murata; Katsumi Ajisaka; Taichi Usui

2000-01-01

455

Polymerized liposomes containing C-glycosides of sialic acid: Potent inhibitors of influenza virus in vitro infectivity  

SciTech Connect

The surface lectin of the influenza virus, hemagglutinin, binds to terminal [alpha]-glycosides of N-acetylneuraminic acid (NeuAc) on cell-surface glycoproteins and glycolipids. Viral binding to cells expression terminal NeuAc residues can be inhibited by [alpha]-O-glycosides of NeuAc (O-sialosides). Recently, dramatic enhancements in the inhibition of viral adhesion to erythrocytes have been achieved using synthetic polyvalent sialosides. In this communication, the authors report that polymerized liposomes containing [alpha]-C-glycosides of sialic acid are potent inhibitors of influenza virus in vitro infectivity. Their results also indicate that the capacity to inhibit hemagglutination does not necessarily reflect the capacity to inhibit in vitro infectivity. 14 refs., 1 tab.

Spevak, W.; Bednarski, M.D.; Nagy, J.O.; Charych, D.H (Lawrence Berkeley Lab., CA (United States)); Schaefer, M.E.; Gilbert, J.H. (Glycomed, Inc., Alameda, CA (United States))

1993-02-10

456

A new group of exo-acting family 28 glycoside hydrolases of Aspergillus niger that are involved in pectin degradation.  

PubMed

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

Martens-Uzunova, Elena S; Zandleven, Joris S; Benen, Jaques A E; Awad, Hanem; Kools, Harrie J; Beldman, Gerrit; Voragen, Alphons G J; Van den Berg, Johan A; Schaap, Peter J

2006-11-15

457

The Structure and Function of an Arabinan-specific [alpha]-1,2Arabinofuranosidase Identified from Screening the Activities of Bacterial GH43 Glycoside Hydrolases  

Microsoft Academic Search

Reflecting the diverse chemistry of plant cell walls, microorganisms that degrade these composite structures synthesize an array of glycoside hydrolases. These enzymes are organized into sequence-, mechanism-, and structure-based families. Genomic data have shown that several organisms that degrade the plant cell wall contain a large number of genes encoding family 43 (GH43) glycoside hydrolases. Here we report the biochemical

Alan Cartmell; Lauren S. McKee; Maria J. Pena; Johan Larsbrink; Harry Brumer; Satoshi Kaneko; Hitomi Ichinose; Richard J. Lewis; Anders Vikso-Nielsen; Harry Gilbert; Jon Marles-Wright

2012-01-01

458

Potent growth inhibitory activity of a novel Ornithogalum cholestane glycoside on human cells: induction of apoptosis in promyelocytic leukemia HL-60 cells.  

PubMed

Growth inhibitory activities of a novel 22-homo-23-norcholestane glycoside found in bulbs of Ornithogalum saundersiae were examined in vitro using human promyelocytic leukemia HL-60 cells, human T-lymphocytic leukemia MOLT-4 cells, and mitogen-stimulated human peripheral-blood mononuclear cells (PBMC). The growth of HL-60 cells and MOLT-4 cells was strongly suppressed in the presence of the glycoside; the IC50s of which were 21.0 and 18.0 nM, respectively. Suppressive effect of the glycoside on HL-60 cell growth appears to be mediated partially through induction of apoptosis which was demonstrated by the presence of DNA fragmentation of the leukemic cells. Flow cytometric analysis of glycoside-treated HL-60 cells also demonstrated apoptotic cells with low DNA content and showed a decrease of G0/G1 cells and a concomitant increase of S and/or G2M cells. The growth inhibiting effect of the glycoside on HL-60 cells was promoted by calcium and was inhibited in the presence of zinc, which support involvement of endonuclease activation in the glycoside-induced apoptosis. The glycoside also inhibited mitogen-stimulated blastogenesis of PBMC, the IC50 of which was 6.2 nM. These results provided the first evidence ever for the potent growth inhibitory activity of Ornithogalum glycoside on human leukemia cell lines and PBMC. PMID:8632726

Hirano, T; Oka, K; Mimaki, Y; Kuroda, M; Sashida, Y

1996-01-01

459

Liquid chromatography combined with thermospray and continuous-flow fast atom bombardment mass spectrometry of glycosides in crude plant extracts.  

PubMed

In crude plant extracts, constituents of biological or pharmaceutical interest often exist in the form of glycosides. Off-line mass spectral investigations of these metabolites require soft ionisation techniques such as desorption chemical ionisation (DCI) or fast atom bombardment (FAB) if information on molecular mass or sugar sequence is desired. In LC-MS, glycosides can be ionised by using thermospray (TSP), continuous-flow fast atom bombardment (CF-FAB) or other interfaces. These techniques are thus potentially applicable to the on-line analysis of glycosides and can be applied to plant extract analysis. Thermospray (TSP) used with ammonium acetate as buffer provides mass spectra similar to those obtained with DCI-MS using NH3 and is potentially applicable to the on-line analysis of relatively small glycosides bearing no more than three sugar units. CF-FAB provides cleaner MS spectra than static FAB due to the lower concentration of the matrix used and can be applied to more polar compounds such as glycosides with a larger number of sugars. The use of a special setup involving post-column addition of the buffer or the matrix and splitting allows LC-UV, TSP LC-MS and CF-FAB LC-MS to be performed with the same standard HPLC conditions. Different crude plant extracts containing various types of glycosides with one to eight sugar units have been analysed by both TSP and CF-FAB. Cardenolides from Nerium odorum (Apocynaceae) and saponins from Swarzia madagascariensis (Leguminosae), Aster scaber and Aster tataricus (Asteraceae) have been studied by LC-MS. The combination of these two interfaces for the HPLC screening of crude plant extracts is discussed. PMID:8556148

Wolfender, J L; Hostettmann, K; Abe, F; Nagao, T; Okabe, H; Yamauchi, T

1995-09-29

460

Flavonoid Glycosides and Naphthodianthrones in the Sawfly Tenthredo zonula and its Host-Plants, Hypericum perforatum and H. hirsutum  

PubMed Central

Larvae of the sawfly Tenthredo zonula are specialized on Hypericum. Whether the sawfly is able to sequester plant metabolites was unknown. Aerial materials of Hypericum perforatum and H. hirsutum, as well as dissected larvae and prepupae of T. zonula, were analyzed by HPLC to determine the presence and content of flavonoid glycosides (rutin, hyperoside, isoquercitrin, and quercitrin) and naphthodianthrones (pseudohypericin and hypericin). All flavonoid glycosides were detected in both Hypericum species, with hyperoside as major compound in H. perforatum (ca. 1.7 ?mol/g fresh weight, FW) and isoquercitrin in H. hirsutum (0.7 ?mol/g FW). Naphthodianthrones were present at low concentrations (0.02 ?mol/g FW) in the former, and almost undetected in the latter species. In the body parts (i.e., hemolymph, digestive tract, salivary glands, or miscellaneous organs) of T. zonula, the surveyed compounds were detected more frequently in prepupae than in larvae. The compounds were not present in every sample, and flavonoid glycosides especially occurred in highly variable amounts, with maximal concentrations of 41 ?g rutin/prepupa in salivary glands, 8 ?g hyperoside/prepupa in hemolymph (= 0.36 ?mol/g FW), 32 ?g isoquercitrin/prepupa in salivary glands, and 63 ?g quercitrin/larva in miscellaneous organs (mainly composed of the integument). We conclude that flavonoid glycosides are sequestered since they were detected in organs other than the digestive tract of larvae, and because prepupae are a non-feeding stage. The naphthodianthrone pseudohypericin, but not hypericin, occurred generally in the digestive tract (up to 0.25 ?g/larva). Both naphthodianthrones and related unidentified compounds, but not flavonoid glycosides, were found in the larval excrement. The highly variable distributions of flavonoid glycosides and naphthodianthrones in T. zonula larvae and prepupae make it difficult to determine the ecological significance of these metabolites.

2012-01-01

461

Cardiac glycosides correct aberrant splicing of IKBKAP-encoded mRNA in familial dysautonomia derived cells by suppressing expression of SRSF3.  

PubMed

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

Liu, Bo; Anderson, Sylvia L; Qiu, Jinsong; Rubin, Berish Y

2013-08-01

462

Cells in Reverse  

NSDL National Science Digital Library

For the first time, scientists have reversed the process of cell division: a trick once thought to be as impossible as un-ringing a bell. Molecular biologist Gary Gorbsky of the Oklahoma Medical Research Foundation led the effort. By tinkering with proteins that regulate the process, they turned the clock back from the end of the cell cycle to the middle.

American Association for the Advancement of Science (;)

2006-05-29

463

Zoellner's reversion spectrometer  

NASA Astrophysics Data System (ADS)

In 1869 K.F. Zoellner (1834-1882), who can be considered as one of the fathers of astrophysics, presented a completely new concept for a radial-velocity spectrometer which he called `Reversionsspektroskop'. The principle of reversion is based on the auto- or cross-correlation method and played an important role in the measurement of stellar radial velocities.

Geyer, E.

464

Time reversal communication system  

DOEpatents

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.

Candy, James V. (Danville, CA); Meyer, Alan W. (Danville, CA)

2008-12-02

465

Reversible cerebral vasoconstriction syndrome.  

PubMed

Reversible cerebral vasoconstriction syndrome (RCVS) is an underdiagnosed condition which usually presents as severe headache with or without neurological deficit. We report the case of a 55-year-old woman who presented with headache and multifocal intracerebral haemorrhage. We review the literature regarding the presentation, pathophysiology and management of RCVS and discuss how to differentiate it from cerebral vasculitis. PMID:24087801

Lee, R; Ramadan, H; Bamford, J

2013-01-01

466

Reversible Thermoelectric Nanomaterials  

Microsoft Academic Search

Irreversible effects in thermoelectric materials limit their efficiency and economy for applications in power generation and refrigeration. While electron transport is unavoidably irreversible in bulk materials, here we derive conditions under which reversible diffusive electron transport can be achieved in nanostructured thermoelectric materials. We provide a fundamental thermodynamic explanation for why the optimum density of states in a thermoelectric material

T. E. Humphrey; H. Linke

2005-01-01

467

Reverse illusions of orientation  

Microsoft Academic Search

The author uses the phrase 'reverse illusions of orientation' to designate a group of facts which have not yet been studied methodically, but which have been cited by many authors and described in different words. These facts consist of illusions or hallucinations of orientation, which arise spontaneously either when we waken in the darkness of night, or during the day

M. Alfred Binet

1894-01-01

468

Soap Bubbles in Reverse  

Microsoft Academic Search

WHEN sulphuric acid sodium sulphate solution containing surface-active material is dropped into water, bubbles approximately 5 mm. in diameter sinking through water may be observed. Such bubbles are spherical shells of air, with a sphere of acid sodium sulphate within and water outside. They are, in fact, soap bubbles in reverse. Instead of a two-surfaced film of soapy solution in

Leslie Rose

1946-01-01

469

The reversal sign.  

PubMed

We report a 36-year-old woman with a bacterial meningitis. CT after resuscitation showed a striking "reversal sign." Opinions on the pathogenesis of this sign are discussed; it indicates serious brain damage and carries a poor prognosis. PMID:1630613

Vergote, G; Vandeperre, H; De Man, R

1992-01-01

470

Biosynthesis of malonylated flavonoid glycosides on the basis of malonyltransferase activity in the petals of Clitoria ternatea.  

PubMed

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

Kogawa, Koichiro; Kazuma, Kohei; Kato, Naoki; Noda, Naonobu; Suzuki, Masahiko

2007-07-01

471

Diterpenoids and phenylethanoid glycosides from the roots of Clerodendrum bungei and their inhibitory effects against angiotensin converting enzyme and ?-glucosidase.  

PubMed

Abietane derivatives, bungnates A, B, 15-dehydrocyrtophyllone A and 15-dehydro-17-hydroxycyrtophyllone A, and two phenylethanoid glycosides, bunginoside A and 3?,4?-di-O-acetylmartynoside, together with nine known abietane derivatives and fourteen known phenylethanoid glycosides, were isolated from dried roots of Clerodendrum bungei. Their structures were determined on the basis of detailed spectroscopic analyses and acidic hydrolysis. The absolute configuration of bunginoside A was established from analysis of CD data. Selected compounds were evaluated for inhibitory effects against angiotensin converting enzyme (ACE) and ?-glucosidase. 15-Dehydrocyrtophyllone A showed an ACE inhibitory effect, and verbascoside, leucosceptoside A and isoacteoside exhibited strong inhibitory capacity against ?-glucosidase. PMID:24726372

Liu, Qing; Hu, Hai-Jun; Li, Peng-Fei; Yang, Ying-Bo; Wu, Li-Hong; Chou, Gui-Xin; Wang, Zheng-Tao

2014-07-01

472

Identification of flavonol and xanthone glycosides from mango (Mangifera indica L. Cv. "Tommy Atkins") peels by high-performance liquid chromatography-electrospray ionization mass spectrometry.  

PubMed

Flavonol O- and xanthone C-glycosides were extracted from mango (Mangifera indica L. cv. "Tommy Atkins") peels and characterized by high-performance liquid chromatography-electrospray ionization mass spectrometry. Among the fourteen compounds analyzed, seven quercetin O-glycosides, one kaempferol O-glycoside, and four xanthone C-glycosides were found. On the basis of their fragmentation pattern, the latter were identified as mangiferin and isomangiferin and their respective galloyl derivatives. A flavonol hexoside with m/z 477 was tentatively identified as a rhamnetin glycoside, which to the best of our knowledge, has not yet been reported in mango peels. The results obtained in the present study confirm that peels originating from mango fruit processing are a promising source of phenolic compounds that might be recovered and used as natural antioxidants or functional food ingredients. PMID:12903961

Schieber, Andreas; Berardini, Nicolai; Carle, Reinhold

2003-08-13

473

HPLC-MSn identification and quantification of flavonol glycosides in 28 wild and cultivated berry species.  

PubMed

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

Mikulic-Petkovsek, Maja; Slatnar, Ana; Stampar, Franci; Veberic, Robert

2012-12-15

474

Two new flavonol glycosides from the Tibetan medicinal plant Aconitum tanguticum.  

PubMed

Two new flavonol glycosides characterized as quercetin 3-O-?-l-rhamnopyranosyl-(1 ? 2)-[?-d-glucopyranosyl-(1 ? 3)-?-l-(4-O-trans-p-coumaroylrhamnopyranosyl)-(1 ? 6)]-?-d-galactopyranoside-7-O-?-l-rhamnopyranoside (1) and kaempferol 3-O-?-l-rhamnopyranosyl-(1 ? 2)-[?-d-glucopyranosyl-(1 ? 3)-?-l-(4-O-trans-p-coumaroyl rhamnopyranosyl)-(1 ? 6)]-?-d-galactopyranoside-7-O-?-l-rhamnopyranoside (2), together with two known flavonol glycosides quercetin 3-O-?-l-rhamnopyranosyl-(1 ? 2)- [?-l-rhamnopyranosyl-(1 ? 6)]-?-d-galactopyranoside-7-O-?-l-rhamnopyranoside (3) and kaempferol 3-O-?-l-rhamnopyranosyl-(1 ? 2)-[?-l-rhamnopyranosyl-(1 ? 6)]-?-d-galactopyranoside-7-O-?-l-rhamnopyranoside (4), were isolated from the whole plant of Aconitum tanguticum (Maxim.) Stapf. The structures of the new compounds were elucidated by spectroscopic methods, and the total (1)H and (13)C NMR chemical shifts were assigned. PMID:23767974

Xu, Lu; Zhang, Xiao; Lin, Li-Mei; Li, Chun; Wang, Zhi-Min; Luo, Yong-Ming

2013-07-01

475

BDNF Mediates Neuroprotection against Oxygen-Glucose Deprivation by the Cardiac Glycoside Oleandrin  

PubMed Central

We have previously shown that the botanical drug candidate PBI-05204, a supercritical CO2 extract of Nerium oleander, provides neuroprot