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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

Diversity of arthropod pests from high latitude peony production  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

3

Quantitative Determination of Digitalis Glycosides in Digitalis Purpurea Leaves by Reversed-Phase Thin-Layer Chromatography  

Microsoft Academic Search

A densitometric reversed-phase thin-layer chromatographic(RP-TLC) method for the determination of digitalis glycosides in Digitalis purpurea leaves has been developed. The procedure involves extraction of dry leaf powder with ethanol\\/chloroform (2:1) and clean-up by Sep-Pak cartridges prior to RP-TLC analysis. RP-TLC was performed on an octadecylsilyl bonded silica gel plate, using a developing solvent of acetonitrile\\/0.5 M NaCl(1 : 1) for

Youichi Fujii; Yukari Ikeda; Mitsuru Yamazaki

1990-01-01

4

'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

5

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

6

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

PubMed

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

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

2015-04-01

7

First Report of Tobacco Rattle Virus in Peony in Alaska  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

8

Cardiovascular and airway relaxant activities of peony root extract.  

PubMed

Paeonia emodi (peony) is a well known plant used medicinally to treat hypertension, palpitations, and asthma. Despite its popularity, there are few reports in the scientific literature examining its use in such conditions. We prepared a 70% ethanolic extract of peony root (Pe.Cr) and applied it to segments of guinea pig atria and trachea and rat aorta suspended separately in tissue baths. Activity against arachidonic acid (AA)-induced platelet aggregation was measured in human platelet-rich plasma. Airway relaxant effect was evaluated against acetylcholine (ACh)-induced airway contraction in mouse lung slices loaded with fluo-4. Pe.Cr (0.3-10 mg/mL) showed an atropine-resistant negative inotropic effect in atria. In rat aorta, an endothelium-independent vasodilatory effect (0.3-10 mg/mL) was seen in phenylephrine- and high-K+-induced contractions. Pe.Cr (0.01-1 mg/mL) also inhibited AA-induced platelet aggregation. In isolated trachea, Pe.Cr (0.3-10 mg/mL) relaxed carbachol- and histamine-induced contractions independently of beta-adrenergic receptors. In mouse lung slices, Pe.Cr (0.3-1 mg/mL) inhibited ACh-induced airway narrowing and oscillations of intracellular Ca2+ in airway smooth muscle cells. The results showed cardiosuppressant, vasodilatory, antiplatelet, and tracheal and airway relaxant activities of peony, providing potential justification for its medicinal use in different hyperactive cardiovascular and respiratory disorders. PMID:19011675

Ghayur, Muhammad N; Gilani, Anwarul H; Rasheed, Huma; Khan, Abdullah; Iqbal, Zafar; Ismail, Muhammad; Saeed, Sheikh A; Janssen, Luke J

2008-11-01

9

Rapid microsatellite development for tree peony and its implications  

PubMed Central

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

2013-01-01

10

Changes in soil microbial community structure with planting years and cultivars of tree peony (Paeonia suffruticosa).  

PubMed

To understand the effects of planting tree peony (Paeonia suffruticosa) on soil microbial community structure, soil samples were collected from the tree peony gardens with three peony cultivars and three planting years, and adjacent wasteland at Luoyang, Henan Province of China. Soil microbial communities were analyzed by the polymerase chain reaction-denaturing gradient gel electrophoresis (PCR-DGGE) of partial 16S rDNA and sequencing methods. With the succeeding development of tree peony garden ecosystems, soil pH, organic C, total P, and available P increased. Soil total N, the cell numbers of bacteria, fungi, and actinomycetes, the Shannon's diversity index (H), richness (S), and Evenness (E(H)) first showed an increasing trend after wasteland was reclaimed and then a decreasing trend became apparent after 5 years of planting. Principal component analysis based on DGGE banding patterns showed that the microbial community structures were influenced by tree peony cultivars and planting years, and the influences of planting years were greater than those of tree peony cultivars. Sequence analysis of the DGGE bands revealed that the dominant bacteria in tree peony garden soils belonged to Proteobacteria, Bacteroidetes, Actinobacteria, Firmicutes, Acidobacteria, Planctomycetes, Euryarchaeota, and Unclassified-bacteria. Moreover, some bacteria closely related to Bradyrhizobium, Sphingopyxis, Novosphingobium, and Sphingomonas, which have been associated with nitrogen fixation and recalcitrant compounds degradation, disappeared with the increasing planting years of tree peony. The bacteria had similarity of 100% compared with Pseudomonas mandelii which was a denitrifying bacteria, and increased gradually with increasing planting years of tree peony. PMID:23933807

Xue, Dong; Huang, Xiangdong

2014-02-01

11

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. PMID:24244590

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

2013-01-01

12

Comparative study of Chinese tree peony cultivars by random amplified polymorphic DNA (RAPD) analysis  

Microsoft Academic Search

Random amplified polymorphic DNA (RAPD) analysis was applied to Chinese tree peony cultivars (Paeonia suffruticosa var. spontanea) to clarify their genetic relationships. Of 40 decamer primers tested, 11 produced 92 useful polymorphic DNA bands. Using these bands, 19 cultivars were distinguished and the similarity values among them were calculated. Although the values between cultivars were high, ranging from 0.722 to

T. Hosoki; D. Kimura; R. Hasegawa; T. Nagasako; K. Nishimoto; K. Ohta; M. Sugiyama; K. Haruki

1997-01-01

13

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

PubMed

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

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

2014-12-22

14

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

PubMed Central

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

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

2014-01-01

15

Genetic and chemical characterization of white and red peony root derived from Paeonia lactiflora.  

PubMed

Two kinds of peony roots--white peony root (WPR) and red peony root (RPR)--are used for different remedies in traditional Chinese medicine; however, most of them are derived from the same botanical origin, Paeonia lactiflora. The difference between WPR and RPR has been debated for a long time. This study attempted to clarify the genetic and chemical characteristics of WPR and RPR in order to provide a scientific dataset for their identification and effective use. The nucleotide sequence of nrDNA internal transcribed spacer (ITS) and the contents of 8 main bioactive constituents were analyzed from specimens of P. lactiflora, P. veitchii and two related species as well as crude drug samples of WPR, RPR and peony root produced in Japan. Of the samples derived from P. lactiflora, the WPR produced in the southern parts of China and the RPR produced in the northern parts of China were clearly divided into two subgroups within the P. lactiflora group based on similarity of the ITS sequences. The nucleotides at positions 69, 458 and 523 upstream of the ITS sequence served as molecular markers to discriminate between WPR and RPR. Quantitative analysis indicated that the RPR samples obviously contained a higher content of paeoniflorin and paeonol, but a lower content of albiflorin than the WPR produced in the southern parts of China and peony root produced in Japan. The WPR available from Chinese markets was usually processed by sulfur fumigation, which resulted in an extremely low content of paeoniflorin. This study indicated that WPR and RPR were not only geographically isolated, but also genetically and chemically separated. The ITS sequence provided a genetic index for their identification. PMID:25151277

Zhu, Shu; Yu, Xiaoli; Wu, Yuqiu; Shiraishi, Fumio; Kawahara, Nobuo; Komatsu, Katsuko

2015-01-01

16

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

PubMed

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

Kubica, Pawe?; Namie?nik, Jacek; Wasik, Andrzej

2015-02-01

17

Iridoidal glycosides from Jasminum sambac  

Microsoft Academic Search

Besides a known trimeric iridoidal glycoside, sambacoside A, five new oligomeric iridoidal glycosides, molihuasides A-E were isolated from the flowers of Jasminum sambac. Their structures were determined by spectral and chemical evidence. Among them, molihuasides A and C-E are new dimeric iridoidal glycosides and molihuaside B is a new trimeric iridoidal glycoside.

Ying-Jun Zhang; Yu-Qing Liu; Xiang-Yu Pu; Chong-Ren Yang

1995-01-01

18

Differential effects of quercetin glycosides on GABAC receptor channel activity.  

PubMed

Quercetin, a representative flavonoid, is a compound of low molecular weight found in various colored plants and vegetables. Quercetin shows a wide range of neuropharmacological activities. In fact, quercetin naturally exists as monomer-(quercetin-3-O-rhamnoside) (Rham1), dimer-(Rutin), or trimer-glycosides [quercetin-3-(2(G)-rhamnosylrutinoside)] (Rham2) at carbon-3 in fruits and vegetables. The carbohydrate components are removed after ingestion into gastrointestinal systems. The role of the glycosides attached to quercetin in the regulation of ?-aminobutyric acid class C (GABAC) receptor channel activity has not been determined. In the present study, we examined the effects of quercetin glycosides on GABAC receptor channel activity by expressing human GABAC alone in Xenopus oocytes using a two-electrode voltage clamp technique and also compared the effects of quercetin glycosides with quercetin. We found that GABA-induced inward current (I GABA ) was inhibited by quercetin or quercetin glycosides. The inhibitory effects of quercetin and its glycosides on I GABA were concentration-dependent and reversible in the order of Rutin ? quercetin ? Rham 1 > Rham 2. The inhibitory effects of quercetin and its glycosides on I GABA were noncompetitive and membrane voltage-insensitive. These results indicate that quercetin and its glycosides regulate GABAC receptor channel activity through interaction with a different site from that of GABA, and that the number of carbohydrate attached to quercetin might play an important role in the regulation of GABAC receptor channel activity. PMID:24895146

Kim, Hyeon-Joong; Lee, Byung-Hwan; Choi, Sun-Hye; Jung, Seok-Won; Kim, Hyun-Sook; Lee, Joon-Hee; Hwang, Sung-Hee; Pyo, Mi-Kyung; Kim, Hyoung-Chun; Nah, Seung-Yeol

2015-01-01

19

Variants of glycoside hydrolases  

SciTech Connect

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

20

Variants of glycoside hydrolases  

SciTech Connect

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

21

Enzymatic synthesis using glycoside phosphorylases  

PubMed Central

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

O’Neill, Ellis C.; Field, Robert A.

2015-01-01

22

Phenylethanoid and lignan glycosides from Verbascum thapsus.  

PubMed

Verbascum thapsus afforded, in addition to three known phenylethanoid glycosides and four lignan ones, five new phenylethanoid glycosides and one new lignan glycoside. Structures of the compounds were elucidated by spectroscopic methods and chemical evidence. PMID:1373629

Warashina, T; Miyase, T; Ueno, A

1992-03-01

23

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

24

The glycosides from Lomatogonium rotatum.  

PubMed

A new phenyl glycoside, 2-(3'-O-beta-D-glucopyranosyl)benzoyloxygentisic acid (1), along with seven known glycosides 2-8 was isolated from Tibetan herbal medicine Lomatogonium rotatum. The structures of the compounds were elucidated by spectroscopic methods including 1D and 2D NMR techniques and MS data. PMID:18266146

Li, Yu-Lin; Suo, You-Rui; Liao, Zhi-Xin; Ding, Li-Sheng

2008-02-15

25

The glycosides from Lomatogonium rotatum  

Microsoft Academic Search

A new phenyl glycoside, 2-(3?-O-?-D-glucopyranosyl)benzoyloxygentisic acid (1), along with seven known glycosides 2–8 was isolated from Tibetan herbal medicine Lomatogonium rotatum. The structures of the compounds were elucidated by spectroscopic methods including 1D and 2D NMR techniques and MS data.

Yu-Lin Li; You-Rui Suo; Zhi-Xin Liao; Li-Sheng Ding

2008-01-01

26

Iridoid glycosides from Thunbergia grandiflora  

Microsoft Academic Search

The novel iridoid glycosides, isounedoside and grandifloric acid, were isolated from Thunbergia grandiflora. Grandifloric acid contains C-10 as a carboxylic acid group, the presence of which was predicted by recent iridoid biosynthesis studies carried out within T. alata. Isounedoside contains a rare 6,7-epoxide functional group. A revision in some of the NMR spectral assignments for the known iridoid glycoside alatoside

Lotfy D. Ismail; Mohamed M. El-Azizi; Taha I. Khalifa; Frank R. Stermitz

1996-01-01

27

Synthesis and photochromic properties of configurationally varied azobenzene glycosides.  

PubMed

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

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

2014-06-01

28

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. PMID:25050228

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

2014-01-01

29

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

PubMed

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

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

2014-11-01

30

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

31

Trans-fused Iridoid GlycosidEs from Penstemon Mucronatus  

Microsoft Academic Search

Two new trans-fused iridoid glycosides (5?H)-6?-8-epidihydrocornin and (5?H)-6?-8-hydroxy-8-epiloganin, were isolated from Penstemon mucronatus, along with cornin, penstemoside and three hastatosides. The trans-fused iridoids are only the second and third known among over 900 described cis-fused iridoid glycosides. Two pairs of iridoids, identical except for the stereochemistry at C-8, were found. Structures were determined by spectroscopic methods.

Robert E. Krull; Frank R. Stermitz

1998-01-01

32

Taraxastane glycosides from Eclipta alba  

Microsoft Academic Search

From the dried whole plants of Eclipta alba (Ecliptae Herba, Chinese name Mo Han Lian) purchased in China, four new taraxastane triterpene glycosides, named eclalbasaponins VII–X were isolated, along with eclalbasaponins I–VI. The structures of eclalbasaponins VII–X were characterized as 3?,20?,16?- and 3?,20?,28-trihydroxytaraxastane glycosides, and their sulphated saponins on the basis of spectral data.

Shoji Yahara; Ning Ding; Toshihiro Nohara; Kazuo Masuda; Hiroyuki Ageta

1997-01-01

33

Iridoid glycosides from Thunbergia grandiflora.  

PubMed

The novel iridoid glycosides, isounedoside and grandifloric acid, were isolated from Thunbergia grandiflora. Grandifloric acid contains C-10 as a carboxylic acid group, the presence of which was predicted by recent iridoid biosynthesis studies carried out within T. alata. Isounedoside contains a rare 6,7-epoxide functional group. A revision in some of the NMR spectral assignments for the known iridoid glycoside alatoside was also made. PMID:8688191

Ismail, L D; el-Azizi, M M; Khalifa, T I; Stermitz, F R

1996-07-01

34

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

PubMed Central

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

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

2014-01-01

35

Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum.  

PubMed

Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox. PMID:24582463

Selenge, Erdenechimeg; Murata, Toshihiro; Tanaka, Shiho; Sasaki, Kenroh; Batkhuu, Javzan; Yoshizaki, Fumihiko

2014-05-01

36

Iridoid glycosides of Cornus canadensis  

Microsoft Academic Search

The iridoid glycosides scandoside, scandoside methyl ester, monotropein, and galioside were found in Cornus canadensis from several widely distributed collection sites. Cornin and hastatoside were isolated from C. nuttallii. No iridoids were found in C. stolonifera, that instead yielded cornoside and halleridone, also independent of collection location. The results were compared with previous studies and current phylogenetic work on the

Frank R Stermitz; Robert E Krull

1998-01-01

37

Flavonol Glycosides from Gaura Biennis  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

38

The Conceptual Metaphor Theory and the Application of Barcelona Sanchez’s Typical Model of Romantic Love to Dream in Peony Pavilion   

E-print Network

This thesis is a report on the application of Barcelona Sanchez’s typical model of romantic love to the Chinese literary work Dream in Peony Pavilion. In this play, the main theme is about love between two young people who are not supposed to have...

Wang, Chenlu

2010-11-25

39

Diterpene glycosides from Stevia rebaudiana.  

PubMed

Three novel diterpene glycosides were isolated for the first time from the commercial extract of the leaves of Stevia rebaudiana, along with several known steviol glycosides, namely stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compounds were identified as 13-[(2-O-?-D-glucopyranosyl-3-O-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-15-en-19-oic acid, 13-[(2-O-?-D-glucopyranosyl-3-O-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy]-16?-hydroxy-ent-kauran-19-oic acid and 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-?-D-glucopyranosyl ester on the basis of extensive 2D NMR and MS spectroscopic data as well as chemical studies. PMID:21527882

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

2011-01-01

40

Phenolic glycosides from Glycosmis pentaphylla.  

PubMed

Three new phenolic glycosides, named as glycopentosides A-C (1-3), along with nine known compounds were isolated from the n-BuOH extract of stems of Glycosmis pentaphylla. Their structures were determined by using spectroscopic and chemical methods. Bioassay showed that compound 10 (tachioside) could inhibit nitric oxide production in lipopolysaccharides-stimulated RAW 264.7 cells with IC50 value of 12.14 ?M. PMID:25367455

Tian, Er-Li; Cui, Yuan-Yuan; Yang, Guang-Zhong; Mei, Zhi-Nan; Chen, Yu

2014-12-01

41

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

42

Flavonol glycosides from Dryas octopetala.  

PubMed

Six flavonol glycosides and ent-epicatechin were isolated from Dryas octopetala and their structures elucidated by chemical and spectroscopic methods. Two new flavonoids, 3-O-alpha-L-arabinofuranosyl-8-methoxyquercetin (2) and 3-O-beta-galactopyranosyl-8-methoxykaempferol (6), were identified along with 3-O-beta-D-galactopyranosylquercetin (hyperin) (3), 3-O-alpha-L-arabinofuranosylquercetin (avicularin) (5), 3-O-beta-L-arabinopyranosylquercetin (4), and 3-O-beta-D-galactopyranosyl-8-methoxyquercetin (1). PMID:6512533

Servettaz, O; Colombo, M L; De Bernardi, M; Uberti, E; Vidari, G; Vita-Finzi, P

1984-01-01

43

Megastigmane glycosides from Salvia nemorosa  

Microsoft Academic Search

From the aerial parts of Salvia nemorosa, three new megastigmane glycosides, salvionosides A-C, were isolated, along with the known compounds, (6S,9R)- and (6S,9S)-roseosides, (6R,9R)- and (6R,9S)-3-oxo-?-ionol glucosides and blumeol C glucoside. The structures of the new compounds were elucidated on the basis of spectral and chemical evidence.

Yoshio Takeda; Hongjie Zhang; Takashi Matsumoto; Hideaki Otsuka; Yasushi Oosio; Gisho Honda; Mamoru Tabata; Tetsuro Fujita; Handong Sun; Ekrem Sezik; Erdem Yesilada

1997-01-01

44

Megastigmane glycosides from Salvia nemorosa.  

PubMed

From the aerial parts of Salvia nemorosa, three new megastigmane glycosides, salvionosides A-C, were isolated, along with the known compounds, (6S,9R)- and (6S,9R)-roseosides, (6R,9R)- and (6R,9S)-3-oxo-alpha-ionol glucosides and blumeol C glucoside. The structures of the new compounds were elucidated on the basis of spectral and chemical evidence. PMID:8983215

Takeda, Y; Zhang, H; Matsumoto, T; Otsuka, H; Oosio, Y; Honda, G; Tabata, M; Fujita, T; Sun, H; Sezik, E; Yesilada, E

1997-01-01

45

[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

46

Identification of flavonoids and expression of flavonoid biosynthetic genes in two coloured tree peony flowers.  

PubMed

Tree peony (Paeonia suffruticosa Andr.) has been named the "king of flowers" because of its elegant and gorgeous flower colour. Among these colours, the molecular mechanisms of white formation and how white turned to red in P. suffruticosa is little known. In this study, flower colour variables, flavonoid accumulation and expression of flavonoid biosynthetic genes of white ('Xueta') and red ('Caihui') P. suffruticosa were investigated. The results showed that the flower colours of both cultivars were gradually deepened with the development of flowers. Moreover, two anthoxanthin compositions apigenin 7-O-glucoside together with apigenin deoxyheso-hexoside were identified in 'Xueta' and 'Caihui', but one main anthocyanin composition peonidin 3,5-di-O-glucoside (Pn3G5G) was only found in 'Caihui'. Total contents of anthocyanins in 'Caihui' was increased during flower development, and the same trend was presented in anthoxanthins and flavonoids of these two cultivars, but the contents of these two category flavonoid in 'Caihui' were always higher than those in 'Xueta'. Furthermore, nine structural genes in flavonoid biosynthetic pathway were isolated including the full-length cDNAs of phenylalanine ammonialyase gene (PAL), chalcone synthase gene (CHS) and chalcone isomerase gene (CHI), together with the partial-length cDNAs of flavanone 3-hydroxylase gene (F3H), flavonoid 3'-hydroxylase gene (F3'H), dihydroflavonol 4-reductase gene (DFR), anthocyanidin synthase gene (ANS), UDP-glucose: flavonoid 3-O-glucosyltransferase gene (UF3GT) and UDP-glucose: flavonoid 5-O-glucosyltransferase gene (UF5GT), and PAL, UF3GT and UF5GT were reported in P. suffruticosa for the first time. Their expression patterns showed that transcription levels of downstream genes in 'Caihui' were basically higher than those in 'Xueta', especially PsDFR and PsANS, suggesting that these two genes may play a key role in the anthocyanin biosynthesis which resulted in the shift from white to red in flowers. These results would provide a better understanding of the underlying molecular mechanisms of flower pigmentation in P. suffruticosa. PMID:25748574

Zhao, Daqiu; Tang, Wenhui; Hao, Zhaojun; Tao, Jun

2015-04-10

47

Effects of total glucosides of peony on immunological hepatic fibrosis in rats  

PubMed Central

AIM: To study the effects of total glucosides of peony (TGP) on immunological hepatic fibrosis induced by human albumin in rats. METHODS: Sixty adult male Sprague-Dawley rats were randomly divided into: Normal group, model group, TGP (60 and 120 mg/kg) treatment groups and colchicines (0.1 mg/kg) treatment group. On the day before the rats were killed, those in TGP or colchicine groups received TGP or colchicine as above from the first day of tail vein injection of human albumin. The rats in normal and model groups were only administered with the same volume of vehicle. At the end of the 16th wk, rats in each group were killed. Blood and tissue specimens were taken. Levels of alanine aminotransferase (ALT), aspartate aminotr-ansferase (AST), nitric oxide (NO), content of malondi-aldehyde (MDA), activity of superoxide dismutase (SOD) and glutathione peroxidase (GSH-px), were measured by biochemical methods. Serum procollagen type III (PC III) and laminin (LN) were determined by radioimmunoassay. Liver collagen level was determined by measuring hydroxyproline content in fresh liver samples. Hepatic tissue sections were stained with hematoxylin-eosin and examined under a light microscope. RESULTS: Histological results showed that TGP improved the human albumin-induced alterations in the liver structure, alleviated lobular necrosis and significantly lowered collagen content. The antifibrotic effect of TGP was also confirmed by decreased serum content of LN and PCIII in TGP-treated group. Moreover, the treatment with TGP effectively reduced the hydroxyproline content in liver homogenates. However, the level of ALT and AST increased in fibrotic rat but had no significance compared with normal control, whereas the ratio of A/G decreased without significance. TGP had no effect on level of ALT, AST and the ratio of A/G. Furthermore, TGP treatment significantly blocked the increase in MDA and NO, asso-ciated with a partial elevation in liver total antioxidant capacity including SOD and GSH-px. CONCLUSION: TGP has beneficial effects on hepatic fibrosis in rats by inhibition of collagen synthesis and decreasing oxidative stress. PMID:15810078

Wang, Hua; Wei, Wei; Wang, Ni-Ping; Wu, Cheng-Yi; Yan, Shang-Xue; Yue, Li; Zhang, Ling-Ling; Xu, Shu-Yun

2005-01-01

48

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

49

Two New Triterpene Glycosides from Centella asiatica  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

50

Systematic qualitative and quantitative assessment of fatty acids in the seeds of 60 tree peony (Paeonia section Moutan DC.) cultivars by GC-MS.  

PubMed

Seeds from Paeonia ostii and Paeoniarockii have been recently identified as novel resources of ?-linolenic acid (ALA) in China. To assess whether tree peony cultivars can be used as oil resource, fatty acids (FAs) in 60 cultivars were monitored and evaluated in this study. The results indicated that the composition and content of FAs varied dramatically among different cultivars, in which ALA, linoleic acid, oleic acid, palmitic acid, and stearic acid were the dominant. The 60 cultivars were classified into six clusters by hierarchical cluster analysis, and they were quite distinct from each other. Finally, six cultivars with high yield and high quality were screened out, comprising of 'Liuliguanzhu', 'Hongguanyupei', 'LSS-2', 'LSS-1', 'Jingshenhuanfa' and 'LSS-11'. These cultivars were appropriately applied in practical oil production. Overall, tree peony oil with abundant unsaturated fatty acids especially ALA was proved to be a top-grade source for edible oil and nutritional supplements. PMID:25466004

Li, Shan-Shan; Yuan, Ru-Yu; Chen, Li-Guang; Wang, Liang-Sheng; Hao, Xiang-Hong; Wang, Li-Jin; Zheng, Xu-Chen; Du, Hui

2015-04-15

51

Hybrid peony ( Paeonia hybrida Pall.), a rare endangered plant of Bashkir Trans-Uralian region: Autocorrelation analysis of the spatial genotype distribution under different environmental conditions  

Microsoft Academic Search

Hybrid peony (Paeonia hybrida Pall.) is listed as endangered in Russian Federation (since 1988) and in several regions of Russia. The structure of the\\u000a isolated population from Bashkir Trans-Uralian region, separated by 1500 km from the main geographic range of this species,\\u000a has been studied using isoenzyme markers from 11 loci. The population is split between two geographical locations, both

N. N. Red’kina; R. Yu. Mullagulov; Yu. A. Yanbaev; A. A. Muldashev; R. Z. Akilov

2008-01-01

52

Pregnane glycosides from Leptadenia pyrotechnica.  

PubMed

The whole plant of Leptadenia pyrotechnica afforded 18 new pregnane glycosides (1-18) with sarcostin, 11-hydroxysarcostin, and deacetylmetaplexigenin as the aglycon moieties and acetyl, benzoyl, cinnamoyl, p-coumaroyl, and nicotinoyl ester moieties linked at C-12 and/or C-20 of the aglycon and hexopyranose, 6-deoxy-3-O-methylhexopyranose, and 2,6-dideoxy-3-O-methylhexopyranose sugars linked at C-3 of their aglycon. The structures of these compounds were elucidated by spectroscopic data interpretation and from chemical evidence. The antiproliferative activity of all compounds was evaluated using three continuous murine and human culture cell lines, J774.A1, HEK-293, and WEHI-164. Compounds having deacethylmetaplexigenin as aglycon and a cinnamoyl ester moiety linked at C-12 were the most active constituents. PMID:16643040

Cioffi, Giuseppina; Sanogo, Rokia; Vassallo, Antonio; Dal Piaz, Fabrizio; Autore, Giuseppina; Marzocco, Stefania; De Tommasi, Nunziatina

2006-04-01

53

Kaempferol glycosides and cardenolide glycosides, cytotoxic constituents from the seeds of Draba nemorosa (Brassicaceae)  

Microsoft Academic Search

Bioassay-directed fractionation of a methanolic extract from the seeds of Draba nemorosa (Brassicaceae) led to isolation of a new flavonol glycoside, drabanemoroside (5, kaempferol 3-O-?-L-rhamnopyranosyl-(1?2)-?-L-arabinopyranose) along with four known flavonoid derivatives (1–4), four cardenolide glycosides (6–9). Kaempferol glycosides 2 and 5 showed strong cytotoxicity against human small lung cancer cell line A549 and melanoma SK-Mel-2 with an IC50 of 0.5

Surk-Sik Moon; Aziz Abdur Rahman; Maniruzzaman Manir; V. S. Jamal Ahamed

2010-01-01

54

[Flavonol glycosides of Sonchus arvensis L].  

PubMed

Two flavone glycoside compounds were isolated from Sonchus arvensis by means of chemical and spectroscopic analysis. They were identified as quercetin-3-O-alpha-L-rhamnoside and kaempferol-3, 7-alpha-L-dirhamnoside. PMID:9388936

Qu, G; Li, X; Liu, J

1996-05-01

55

A new diterpene glycoside from Stevia rebaudiana.  

PubMed

From the commercial extract of the leaves of Stevia rebaudiana, a new diterpene glycoside was isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compound was identified as 13-[(2-O-?-D-glucopyranosyl-3-O-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O-?-L-rhamnopyranosyl-?-D-glucopyranosyl) ester (1) on the basis of extensive spectroscopic (NMR and MS) and chemical studies. PMID:21464800

Chaturvedula, Venkata Sai Prakash; Prakash, Indra

2011-01-01

56

Cycloartane triterpene glycosides from Astragalus trigonus  

Microsoft Academic Search

Three new cycloartane glycosides, trigonoside I, II and III, and the known astragalosides I and II were isolated from the roots of Astragalus trigonus. The structures of the new glycosides were totally elucidated by high field (600 MHz) NMR analyses as cycloastragenol-6-O-?-xylopyranoside, cycloastragenol-3-O-[?-l-arabinopyranosyl(1 ? 2)-?-d-xylopyranosyl]-6-O-?- d-xylopyranoside and cycloastragenol-3-O-[?-l-arabinopyranosyl(1 ? 2)-?-d-(3-O-acetyl)-xylopyranosyl]-6-O-?-d-xylopyranoside.

Pierluigi Gariboldi; Francesca Pelizzoni; Marco Tatò; Luisella Verotta; Nadia El-Sebakhy; Aya M. Asaad; Rokia M. Abdallah; Soad M. Toaima

1995-01-01

57

Triterpenoid glycosides from Anagallis arvensis.  

PubMed

From the herb of Anagallis arvensis, we have isolated four novel oleanane glycosides, anagallosaponins VI-IX, and two artifact saponins, apoanagallosaponins III and IV, formed from anagallosaponins III and IV. The structures were elucidated by chemical and spectral methods, 2D NMR techniques being particularly helpful. The structures of anagallosaponins VI and VII were characterized as priverogenin B 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside), respectively. The structures of anagallosaponins VIII and IX were characterized as 23-hydroxypriverogenin B 22-acetate 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]- alpha-L-arabinopyranoside), respectively. The structures of apoanagallosaponins III and IV were characterized as camelliagenin A 16-acetate 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabnopyranoside, 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), respectively. PMID:7765757

Shoji, N; Umeyama, A; Yoshikawa, K; Arihara, S

1994-11-01

58

FLAVONE C-GLYCOSIDES AND CUCURBITACIN GLYCOSIDES FROM CITRULLUS COLOCYNTHIS  

Microsoft Academic Search

Citrullus colocynthis (L.) Schrad. (Cucurbitaceae) is an Iranian medicinal plant that has traditionally been used as an abortifacient and to treat constipation, oedema, bacterial infections, cancer and diabetes. As part of our on-going studies on Iranian medicinal plants, thorough phytochemical investigation was carried out on this plant. The reversed-phase preparative HPLC was employed to isolate compounds from the butanol fraction

SIMON GIBBONS; ALI REZA KOSARI; MASOUD MODARRESI; SATYAJIT D. SARKER

2006-01-01

59

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

60

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

61

Sesquiterpene lactone glycosides from Arnica longifolia.  

PubMed

Flowers of ARNICA LONGIFOLIA were investigated for the occurrence of sesquiterpene lactone glycosides. A mixture containing the two isomeric 11alpha,13-dihydro- and 11beta,13-dihydro-4 H-tomentosin glucosides, previously isolated from A. AMPLEXICAULIS and A. MOLLIS, together with the two isomeric 11alpha,13-dihydro- and 11beta,13-dihydro-4 H-carabrone glucosides were found in A. LONGIFOLIA. All carbon and proton shifts of the glycosides could be assigned by their 2D-COSY and 2D-HETCOR spectra and spectroscopy of their respective aglycones, obtained via enzymatic hydrolysis. PMID:17260246

Passreiter, C M; De Carlo, M; Steigel, A

1999-03-01

62

Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana  

Microsoft Academic Search

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.

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

2007-01-01

63

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

64

Kaempferol glycosides and cardenolide glycosides, cytotoxic constituents from the seeds of Draba nemorosa (Brassicaceae).  

PubMed

Bioassay-directed fractionation of a methanolic extract from the seeds of Draba nemorosa (Brassicaceae) led to isolation of a new flavonol glycoside, drabanemoroside (5, kaempferol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranose) along with four known flavonoid derivatives (1-4), four cardenolide glycosides (6-9). Kaempferol glycosides 2 and 5 showed strong cytotoxicity against human small lung cancer cell line A549 and melanoma SK-Mel-2 with an IC(50) of 0.5 microg/mL and 1.9 microg/mL, respectively. Cardenolide glycosides 6-9 showed potent cytotoxicity (A549) in the range of 0.01-0.032 microg/mL. Their structures were characterized based on spectroscopic data (2D NMR, HRTOFMS, IR, and UV) and comparison of literature values. The carbohydrate units were also confirmed by comparing the hydrolysate of 5 with authentic monosaccharides. PMID:20803119

Moon, Surk-Sik; Rahman, Md Aziz Abdur; Manir, Md Maniruzzaman; Jamal Ahamed, V S

2010-08-01

65

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

PubMed Central

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

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

2015-01-01

66

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

PubMed Central

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

67

Synthesis of cardenolide glycosides and putative biosynthetic precursors of cardenolide glycosides  

Microsoft Academic Search

A rapid and efficient procedure for glycosylation of steroids was established using a modified Koenigs–Knorr procedure. Peracetylated ?-glycosides were synthesized by reaction of cardenolides, various pregnanes and 23-nor-5,20(22)E-choldienic acid at room temperature with the peracetylated 1-bromo derivatives of d-glucose, d-galactose, d-fucose and cellobiose. Subsequent deprotection was performed by alkaline hydrolysis with sodium methoxide. Structures of the respective glycosides were established

Melitta Luta; Andreas Hensel; Wolfgang Kreis

1998-01-01

68

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

69

Jaspolyside, a secoiridoid glycoside from Jasminum polyanthum  

Microsoft Academic Search

A new secoiridoid glucoside, jaspolyside was isolated from the leaves of Jasminum polyanthum along with nine known secoiridoid glycosides: oleoside dimethyl ester, 10-hydroxyoleoside dimethyl ester, oleoside 11-methyl ester, methyl-glucooleoside, 8-epi-kingiside, ligustroside, angustifolioside B, oleuropein, and oleoacetoside. The structure of the new compound has been established on the basis of spectral and chemical methods.

Ya-Ching Shen; Saho-Ling Lin; Chyh-Chung Chein

1996-01-01

70

Two new secoiridoid glycosides from Gentiana algida.  

PubMed

Two new acylated secoiridoid glycosides were isolated from the aqueous acetone extract of the whole herb of Gentiana algida. The structures of these new products were established by spectral and chemical methods as 6'-(2,3-dihydroxybenzoyl)sweroside and 6'-(2,3-dihydroxybenzoyl)swertiamarin, respectively. PMID:17252380

Tan, R X; Hu, J; Dong, L D; Wolfender, J L; Hostettmann, K

1997-12-01

71

Two new secoiridoid glycosides from Verbena officinalis.  

PubMed

Two new secoiridoid glycosides, verbenoside A (1) and verbenoside B (2), have been isolated from the ethanol extract of the aerial parts of Verbena officinalis L. Their structures were elucidated on the basis of spectroscopic evidences, especially 1D, 2D NMR, and MS experiments. PMID:20706899

Xu, Wei; Xin, Fei; Sha, Yi; Fang, Jin; Li, Yu-Shan

2010-08-01

72

Twisting of glycosidic bonds by hydrolases  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

73

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

74

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

Søren Bak; Susanne Michelle Paquette; Marc Morant; Anne Vinther Morant; Shigeki Saito; Nanna Bjarnholt; Mika Zagrobelny; Kirsten Jørgensen; Sarah Osmani; Henrik Toft Simonsen; Raquel Sanchez Pérez; Torbjørn Bordier van Heeswijck; Bodil Jørgensen; Birger Lindberg Møller

2006-01-01

75

Phenolic glycosides from berries of Pimenta dioica.  

PubMed

Four new phenolic glycosides, (2-hydroxy-3-methoxy-5-allyl)phenyl beta- d-(6-O-E-sinapoyl)glucopyranoside (1), (1' R,5' R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3 Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. PMID:18314960

Kikuzaki, Hiroe; Miyajima, Yoshiko; Nakatani, Nobuji

2008-05-01

76

Polyhydroxylated steroidal glycosides from Paris polyphylla.  

PubMed

Three new steroidal saponins, parisyunnanosides G-I (1-3), one new C(21) steroidal glycoside, parisyunnanoside J (4), and three known compounds, padelaoside B (5), pinnatasterone (6), and 20-hydroxyecdyson (7), were isolated from the rhizomes of Paris polyphylla Smith var. yunnanensis. Compounds 1 and 3 have unique trisdesmoside structures that include a C-21 ?-d-galactopyranose moiety. All compounds were evaluated for their cytotoxicity against human CCRF leukemia cells. PMID:22663190

Kang, Li-Ping; Liu, Yi-Xun; Eichhorn, Tolga; Dapat, Else; Yu, He-shui; Zhao, Yang; Xiong, Cheng-Qi; Liu, Chao; Efferth, Thomas; Ma, Bai-Ping

2012-06-22

77

New Pregnane Glycosides from Gymnema sylvestre.  

PubMed

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

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

2015-01-01

78

Three acylated flavone glycosides from sideritis syriaca  

Microsoft Academic Search

From the aerial parts of Sideritis syriaca a new flavone glycoside, 5,8,3?-trihydroxy-4?-methoxyflavone 7-(6?-O-acetylsophoroside) was identified together with apigenin 7-(6?-p-coumaroylglucoside) and apigenin 7-(4?-p-coumaroylglucoside) which are reported for the first time in the genus Sideritis. The compounds were characterized using 1HNMR, 13CNMR, MS and chemical methods.

Pietro Venturella; Aurora Bellino; Maria Luisa Marino

1995-01-01

79

Three acylated flavone glycosides from Sideritis syriaca.  

PubMed

From the aerial parts of Sideritis syriaca a new flavone glycoside, 5,8,3'-trihydroxy-4'-methoxyflavone 7-(6"'-O-acetylsophoroside) was identified together with apigenin 7-(6"-p-coumaroylglucoside) and apigenin 7-(4"-p-coumaroylglucoside) which are reported for the first time in the genus Sideritis. The compounds were characterized using 1H NMR, 13C NMR, MS and chemical methods. PMID:7772308

Venturella, P; Bellino, A; Marino, M L

1995-01-01

80

A new monoterpene glycoside from Siparuna thecaphora.  

PubMed

Phytochemical investigation of the extracts of the leaves of Siparuna thecaphora (Poepp. et Endl.) A. DC. (Siparunaceae) allowed the isolation of one monoterpene glycoside, named trans-thujane-1?,7-diol 1-O-?-D-glucopyranoside (1) along with rutin, quercetin 3-O-?-D-glucopyranoside and 3,4-dihydroxybenzaldehyde. Their structural characterisation was obtained on the basis of extensive spectroscopic analyses, including 1D and 2D NMR experiments and HR-ESI-MS. PMID:24087860

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

2014-01-01

81

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

82

Oleandrin: A cardiac glycosides with potent cytotoxicity  

PubMed Central

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.

2013-01-01

83

[Triterpene glycosides and the structural-functional properties of membranes].  

PubMed

Triterpene glycosides have been found in many plant species and some marine animals. Many of these compounds are physiologically active and possess a broad range of medico-biological action. The physiological activity of triterpene glycosides is based on their ability to interact with the components of biological systems, primarily with sterols comprising the structure of biomembranes. The interaction of glycosides with sterols causes disturbance of selective permeability in plasmic membranes. Triterpene glycosides affect the liposome ionic permeability and flat bilayer lipid membranes. The rate of glycoside effect depends on quantitative and qualitative sterol level in the membrane. These compounds are used by organisms in the struggle for life and in maintaining the biological equilibrium in the antagonistic interactions of biological systems and ensure plant immunity against fungal diseases. Triterpene glycosides as substances of exogenous origin exhibit physiological activity towards warm-blooded animals. They affect the metabolism, the functional state of the organs and the organism as a whole. PMID:3322414

Anisimov, M M

1987-01-01

84

Facile access to new C-glycosides and C-glycoside scaffolds incorporating functionalised aromatic moieties.  

PubMed

The tandem ene/intramolecular Sakurai cyclisation (IMSC) reaction has been successfully applied to the synthesis of a range of C-glycosides, with key intermediates offering opportunities for functionalisation of the glycon moiety. To demonstrate the versatility of the approach to access the 2-deoxy-C-glycoside series, we synthesised diastereomerically pure C-glucoside and galactoside derivatives incorporating functionalised aromatic, heteroaromatic and bicyclic aromatic moieties, in addition to the C-homologue of (±)-?-2-deoxy-glucose 6-phosphate. PMID:25486220

Redpath, Philip; Ness, Kerry A; Rousseau, Joanne; Macdonald, Simon J F; Migaud, Marie E

2015-01-30

85

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

86

Monitoring plasmon-driven surface catalyzed reactions in situ using time-dependent surface-enhanced Raman spectroscopy on single particles of hierarchical peony-like silver microflowers  

NASA Astrophysics Data System (ADS)

Investigating the kinetics of catalytic reactions with surface-enhanced Raman scattering (SERS) on a single particle remains a significant challenge. In this study, the single particle of the constructed hierarchical peony-like silver microflowers (SMFs) with highly roughened surface led to the coupling of high catalytic activity with a strong SERS effect, which acts as an excellent bifunctional platform for in situ monitoring of surface catalytic reactions. The kinetics of the reaction of 4-nitrothiophenol (4-NTP) dimerizing into 4,4'-dimercaptoazobenzene (DMAB) was investigated and comparatively studied by using the SERS technique on a single particle of different morphologies of SMFs. The results indicate that a fully developed nanostructure of a hierarchical SMF has both larger SERS enhancement and apparent reaction rate constant k, which may be useful for monitoring and understanding the mechanism of plasmon-driven surface catalyzed reactions.Investigating the kinetics of catalytic reactions with surface-enhanced Raman scattering (SERS) on a single particle remains a significant challenge. In this study, the single particle of the constructed hierarchical peony-like silver microflowers (SMFs) with highly roughened surface led to the coupling of high catalytic activity with a strong SERS effect, which acts as an excellent bifunctional platform for in situ monitoring of surface catalytic reactions. The kinetics of the reaction of 4-nitrothiophenol (4-NTP) dimerizing into 4,4'-dimercaptoazobenzene (DMAB) was investigated and comparatively studied by using the SERS technique on a single particle of different morphologies of SMFs. The results indicate that a fully developed nanostructure of a hierarchical SMF has both larger SERS enhancement and apparent reaction rate constant k, which may be useful for monitoring and understanding the mechanism of plasmon-driven surface catalyzed reactions. Electronic supplementary information (ESI) available: Fig. S1-S12. See DOI: 10.1039/c4nr01939c

Tang, Xianghu; Cai, Wenya; Yang, Liangbao; Liu, Jinhuai

2014-07-01

87

Physical mapping of ribosomal RNA genes in peonies (Paeonia, Paeoniaceae) by fluorescent in situ hybridization: implications for phylogeny and concerted evolution.  

PubMed

Physical maps of the 18S-5.8S-26S ribosomal RNA genes (rDNA) were generated by fluorescent in situ hybridization for five diploid Paeonia species, P. delavayi and P. rockii of section Moutan, and P. emodi, P. tenuifolia, and P. veitchii of section Paeonia. Of five pairs of mitotic chromosomes, rDNA loci were mapped near the telomeres of chromosomes 3, 4, and 5 of P. rockii and P. tenuifolia, chromosomes 2, 3, 4, and 5 of P. delavayi, and all five pairs of chromosomes of P. emodi and P. veitchii. Combining this information with the previously obtained rDNA maps of P. brownii and P. californica of section Oneapia, we hypothesized that the most recent common ancestor of extant peony species had three rDNA loci located on chromosomes 3, 4, and 5. Increase in number of rDNA loci occurred later in each of the three sections, and the increase from three to four loci represents a parallel gain of an rDNA locus on chromosome 2 in P. delavayi of section Moutan and P. brownii of section Oneapia. The increase in number of rDNA loci likely resulted from the translocation of rDNA repeats from chromosomes bearing rDNA loci to chromosomes without them; such translocation is probably facilitated by the telomeric location of rDNA loci. For allotetraploid peony species lacking polymorphism in sequences of the internal transcribed spacers (ITS) of rDNA, the rDNAs derived from divergent diploid parents may have been homogenized through concerted evolution among at least six rDNA loci in the allotetraploids. Chromosomal location of rDNA loci has a more substantial impact on the tempo of concerted evolution than the number of loci. PMID:10330077

Zhang, D; Sang, T

1999-05-01

88

Additional minor diterpene glycosides from Stevia rebaudiana.  

PubMed

From the commercial extract of the leaves of Stevia rebaudiana, two additional new diterpenoid glycosides were isolated and their structures were characterized as 13-[(2-O-beta-glucopyranosyl-3-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid beta-D-glucopyranosyl ester (1) and 13-[(2-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid beta-D-glucopyranosyl ester (2) on the basis of extensive spectral data (NMR and MS) and chemical studies. PMID:21922898

Chaturvedula, Venkata Sai Prakash; Prakash, Indra

2011-08-01

89

Cardiac glycosides of Cheiranthus allioni. XIII. Glucoerycordin  

Microsoft Academic Search

From plains erysimum (Cheiranthus allioni) Hort., (Erysimum asperum) a new cardiac glycoside has been isolated which has been called glucoerycordin. Its chemical structure has been established mainly by stepwise hydrolysis and the identification of the hydrolysis products. Glucoerycordin C41H64 O19, mp 131–135°C, [a]D20 -22.2 ± 3° (c 0.65; methanol) is 3ß-[O-ß-D-glucopyranosyl-(1 ? 4)-O-ß-D-glycopyranosyl-(1 ? 4)-gulomethylopyranosyloxy]-14,19-dihydroxy-5ß, 14ß-card-20(22)-enolide.

I. F. Makarevich; A. I. Pavlii; S. I. Makarevich

1989-01-01

90

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

91

Phenolic glycosides of forage legume Onobrychis viciifolia.  

PubMed

A chemical examination of the extractives of the leaves of sainfoin was undertaken as part of a programme directed at understanding the factors which may contribute to its nutritive value as animal feed. Among the low molecular weight phenolic compounds characterized were seven cinnamic acid derivatives and nine flavonoid glycosides all of which were identified by NMR spectroscopy. Included among these compounds were two new natural hydroxycinnamic esters namely methyl 6-O-p-trans-coumaroyl-beta-D-glucopyranoside and methyl 6-O-p-cis-coumaroyl-beta-D-glucopyranoside and a novel flavonoid chrysoeriol-4'-O-(6''-O-acetyl)-beta-D-glucopyranoside. PMID:11021646

Lu, Y; Sun, Y; Foo, L Y; McNabb, W C; Molan, A L

2000-09-01

92

Chromone glycosides and flavonoids from hypericum japonicum  

Microsoft Academic Search

From the aerial parts of Hypericum japonicum, two novel chromone glycosides, 5, 7-dihydroxy-2-(1-methylpropyl) chromone-8-?-d-glucoside and 5, 7-dihydroxy-2-isopropylchromone-8-?-d-glucoside, and two new flavonoids, 7, 8-(2?, 2?-dimethylpyrano)-5, 3?, 4?-trihydroxy-3-mehoxyflavone and (2R, 3R) dihydroquercetin-3, 7-O-?-l-dirhamnoside were isolated together with nine known flavonoids. Their structures were deduced from spectroscopic and chemical evidence. Some of the compounds were found to exert an interesting coagulant activity in

Qing-Li Wu; Sheng-Ping Wang; Li-Jun Du; Shu-Ming Zhang; Jun-Shan Yang; Pei-Gen Xiao

1998-01-01

93

Sesquiterpenoid Tropolone Glycosides from Liriosma ovata.  

PubMed

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

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

2015-02-27

94

Protein binding of anthraquinone glycosides, with special reference to adriamycin  

Microsoft Academic Search

The binding of anthraquinone glycosides (adriamycin, adriamycinol, daunorubicin, daunorubicinol, and 4' epiadriamycin) to human serum albumin and human plasma has been studied by equilibrium dialysis. About 62% of adriamycin was bound to human serum albumin (45 g\\/l). Only minor variations in the degree of binding were observed between the anthraquinone glycosides.

Staffan Eksborg; Hans Ehrsson; Britta Ekqvist

1982-01-01

95

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

96

Phytosteryl glycosides reduce cholesterol absorption: mechanisms in mice  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

97

The insulin receptor glycosidic moiety : its characterization and role  

E-print Network

-linked type play a key role at both insulin receptor and post-receptor levels. Introduction. Over the past tenThe insulin receptor glycosidic moiety : its characterization and role Martine CARON, Gisèle exoglycosidases and/or lectins as specific glycosidic probes, we characterized the insulin receptor carbohydrate

Paris-Sud XI, Université de

98

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. PMID:24895612

Calderón-Montaño, José Manuel; Burgos-Morón, Estefanía; Orta, Manuel Luis; Maldonado-Navas, Dolores; García-Domínguez, Irene; López-Lázaro, Miguel

2014-01-01

99

Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius  

E-print Network

Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius Meltem O¨ zipek a oleifoliosides A (1) and B (2) were isolated from the lower stem parts of Astragalus oleifo- lius rights reserved. Keywords: Astragalus oleifolius; Leguminosae; Cycloartane-type glycoside; Oleifoliosides

Rüedi, Peter

100

Verbascoside derivatives and iridoid glycosides from Penstemon crandallii  

Microsoft Academic Search

The new phenylethanoid glycosides 2-O-acetyl-3?-O-methylverbascoside and 2,4?-di-O-acetyl-3?-O-methylverbascoside were isolated and identified from Penstemon crandallii. The major iridoid glycoside was plantarenaloside and no aucubin type iridoids were found. This contrasted with a previous analysis of P. teucrioides, from the same Penstemon subsection, which was dominated by aucubin derivatives.

Lotfy D. Ismail; Mohamed M. El-Azizi; Taha I. Khalifa; Frank R. Stermitz

1995-01-01

101

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. PMID:24949266

2014-01-01

102

[Cardiac glycosides: From ancient history through Withering's foxglove to endogeneous cardiac glycosides].  

PubMed

For centuries, drugs that increase the power of contraction of the failing heart have been used for the treatment of congestive heart failure (dropsy). The cardiac effect is due to the content of cardiac glycosides. Squill or sea onion, Urginea (Scilla) maritima, a seashore plant, was known by the ancient Romans and Syrians and possibly also by the ancient Egyptians. Squills were used erratically, but some prescriptions indicate that they may have been used for the treatment of oedematous states. The toxic effect of strophanthus species was known from poisoned arrows used by the natives in Africa. Digitalis, derived form the foxglove plant, Digitalis purpurea, is mentioned in writings as early as 1250; a Welsh family, known as the Physicians of Myddvai, collected different herbs and digitalis was included in their prescriptions. However, the druge was used erratically until the 18th century, when William Withering, an English physician and botanist, published a monograph describing the clinical effects of an extract of the foxglove plant. Later, in 1785, the indication and the toxicity of digitalis were reported in his book, "An account of the Foxglove and some of its medical uses with practical remarks on dropsy, and other diseases". In Denmark, the leaves of Digitalis purpurea or Digitalis lanata were tested for cardiac glycoside activity. The standardized digitalis powder was used in tinctures, infusions, and tablets. The preparations were included in successive editions of the Danish pharmacopoeia, some of the tinctures already in 1828, i.e. before the standardization of the drug. Isolation of cardiac glycosides from digitalis, strophanthus and squill and determination of their chemical structures initiated biochemical and pharmacological studies. The scientific advances led to an understanding of cardiac muscle contractility and the Na,K pump as the cellular receptor for the inotropic action of digitalis. Examination of putative endogenous ligands to the receptor revealed some endogenous cardiac glycosides of similar or identical structures as those found in digitalis, strophanthus and squill. Increased concentrations of these glycosides are found in patients with heart failure. Further investigations are needed to determine whether the secretion of glycosides might be a physiologic response to a diminished cardiac output. PMID:15685783

Norn, Svend; Kruse, Poul R

2004-01-01

103

Synthesis of cardenolide glycosides and putative biosynthetic precursors of cardenolide glycosides.  

PubMed

A rapid and efficient procedure for glycosylation of steroids was established using a modified Koenigs-Knorr procedure. Peracetylated beta-glycosides were synthesized by reaction of cardenolides, various pregnanes and 23-nor-5,20(22)E-choldienic acid at room temperature with the peracetylated 1-bromo derivatives of D-glucose, D-galactose, D-fucose and cellobiose. Subsequent deprotection was performed by alkaline hydrolysis with sodium methoxide. Structures of the respective glycosides were established by NMR techniques. The complete protocol was shown to be non-destructive at all stages to the sugar moiety and the steroidal nucleus. The gamma-unsaturated lactone ring of the cardenolides was shown to remain intact and no formation of C-14 unsaturated compounds was observed. PMID:9437794

Luta, M; Hensel, A; Kreis, W

1998-01-01

104

Biosynthesis of daunorubicin glycosides: role of epsilon-rhodomycinone.  

PubMed Central

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

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

1980-01-01

105

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

PubMed

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

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

2015-01-01

106

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

PubMed

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

Gonda, Sándor; Nguyen, Nhat Minh; Batta, Gyula; Gyémánt, Gyöngyi; Máthé, Csaba; Vasas, Gábor

2013-09-01

107

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

108

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

109

Spectroscopic manifestation of stretching vibrations of glycosidic linkage in polysaccharides  

NASA Astrophysics Data System (ADS)

Manifestation of stretching vibrations of glycosidic linkage in the infrared spectra of polysaccharides (native, microcrystalline, mercerized celluloses, amylose, starches) has been studied using the regularized method of deconvolution. It has been shown that the glycosidic linkage formation in the polysaccharides is characterized by the appearance of new absorption bands in the 1175-1140 cm -1 range as compared to their corresponding monomers. In the 1000-920 cm -1 region differences between the infrared spectra of polysaccharides due to the changes in the glycosidic linkage configuration have been found.

Nikonenko, N. A.; Buslov, D. K.; Sushko, N. I.; Zhbankov, R. G.

2005-10-01

110

Spectrophotometric estimation of individual flavone glycosides in three Euphorbia species.  

PubMed

Two spectrophotometric methods (conventional and differential) are carried out for the estimation of flavone glycosides (hyperoside and/or kaempferol-3-beta-glucoside) in Euphorbia paralias L., and Euphorbia helioscopia L. The glycosides are extracted with methanol from the aerial parts of the different Euphorbia species, separated on silica gel chromatoplates, and eluted by refluxing with methanol (80%). The absorbance value (conventional method) and the delta absorbance value (differential method) of the prepared glycosidal solutions are measured. The results of both methods are of conveinent reproducibility. PMID:1161795

Abdel-Salam, N A; El-Sayed, M; Khafagy, S M

1975-06-01

111

Five new flavonoid glycosides from Nervilia fordii.  

PubMed

Five new flavonoid glycosides, namely nervilifordins F-J (1-5), were isolated from the 60% EtOH extract of the aerial parts of Nervilia fordii, along with three first isolated flavonoids (7, 8, and 13) and five known flavonoids (6, 9-12). The structures of new compounds were elucidated on the basis of 1D and 2D NMR and MS studies. Their anti-inflammatory activities were tested by measuring their inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages. Compounds 2 and 5 showed interesting inhibition effects with their EC50 values of 15.15 ?M and 14.80 ?M, respectively. PMID:23659497

Qiu, Li; Jiao, Yang; Xie, Ji-Zhao; Huang, Gui-Kun; Qiu, Shao-Ling; Miao, Jian-Hua; Yao, Xin-Sheng

2013-01-01

112

Flavone C-glycosides from Bryonia alba and B. dioica  

Microsoft Academic Search

Lutonarin was isolated from Bryonia alba and B. dioica. Five further C-glycosides: vitexin, isovitexin, isoorientin, saponarin were isolated from B. dioica together with saponarin caffeic ester, a new natural product.

Miroslawa Krauze-Baranowska; Wojciech Cisowski

1995-01-01

113

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

114

Flavonol glycosides from the flowers of Bellis perennis.  

PubMed

Three flavonol glycosides, isorhamnetin 3-O-beta-D-galactopyranoside, isorhamnetin 3-O-beta-D-(6"-acetyl)-galactopyranoside and kaempferol 3-O-beta-D-glucopyranoside were isolated from the flowers of Bellis perennis. PMID:11677029

Gudej, J; Nazaruk, J

2001-11-01

115

Flavonol glycosides from the flowers of Bellis perennis  

Microsoft Academic Search

Three flavonol glycosides, isorhamnetin 3-O-?-d-galactopyranoside, isorhamnetin 3-O-?-d-(6?-acetyl)-galactopyranoside and kaempferol 3-O-?-d-glucopyranoside were isolated from the flowers of Bellis perennis.

J Gudej; J Nazaruk

2001-01-01

116

A new aryl glycoside from Euphorbia helioscopia L  

Microsoft Academic Search

A new aryl glycoside, 3?-O-galloyl-benzyl-O-?-l-rhamnopyranosyl-(1?6)-?-d-glucopyranoside, was isolated from Euphorbia helioscopia L., and its structure was elucidated on the basis of various spectroscopic data analysis.

Wei Sheng Feng; Li Gao; Xiao Ke Zheng; Yan Zhi Wang

2009-01-01

117

A new lathyrane diterpene glycoside from Euphorbia helioscopia L  

Microsoft Academic Search

A new lathyrane diterpene glycoside, named 3?, 7?, 15?-trihydroxy-14-oxolathyra-5E, 12E-dienyl-16-O-?-d-glucopyranoside, was isolated from Euphorbia helioscopia L. Its structure was established by spectroscopic techniques including 2D NMR.

Wei Sheng Feng; Li Gao; Xiao Ke Zheng; Yan Zhi Wang; Hui Chen

2010-01-01

118

Two new triterpenoidal glycosides from Medicago polymorpha L.  

PubMed

Two new triterpenoid glycosides called medicago-saponins P1 (1) and P2 (2) were isolated together with five known glycosides from the aerial parts of Medicago polymorpha L. (Leguminosae). The structures of 1 and 2 were determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl caulophyllogenin 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside and the desglucoside of 1. PMID:8069980

Kinjo, J; Uemura, H; Nakamura, M; Nohara, T

1994-06-01

119

A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis.  

PubMed

A new phenylpropanoid glycosides, 2-feruloyl-O-alpha-D-glucopyranoyl-(1'-->2)-3,6-O-feruloyl-beta-D-fructofuranoside, was isolated from the root of Paris polyphylla var. yunnanensis. The structure of the new glycoside was elucidated by spectroscopic methods. Cytotoxicity test showed that it has cytotoxic effect in a dose-dependent manner against the mice lung adenocarcinoma cell line (LA795). PMID:18353566

Yan, Lulu; Gao, Wenyuan; Zhang, Yanjun; Wang, Yu

2008-06-01

120

Furostanol glycosides from the rhizomes of Helleborus orientalis.  

PubMed

Eight new furostanol glycosides (1-8), together with two known ones (9 and 10), have been isolated from a glycoside-enriched fraction prepared from the rhizomes of Helleborus orientalis (Ranunculaceae). The structures of 1-8 were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HSC-2 cells. PMID:20563660

Mimaki, Yoshihiro; Matsuo, Yukiko; Watanabe, Kazuki; Sakagami, Hiroshi

2010-10-01

121

Characterization and Synergistic Interactions of Fibrobacter succinogenes Glycoside Hydrolases  

Microsoft Academic Search

The objectives of this study were to characterize Fibrobacter succinogenes glycoside hydrolases from different glycoside hydrolase families and to study their synergistic interactions. The gene encoding a major endoglu- canase (endoglucanase 1) of F. succinogenes S85 was identified as cel9B from the genome sequence by reference to internal amino acid sequences of the purified native enzyme. Cel9B and two other

Meng Qi; Hyun-Sik Jun; Cecil W. Forsberg

2007-01-01

122

Verbascoside derivatives and iridoid glycosides from Penstemon crandallii.  

PubMed

The new phenylethanoid glycosides 2-O-acetyl-3'''-O-methylverbascoside and 2,4"-di-O-acetyl-3'''-O-methylverbascoside were isolated and identified from Penstemon crandallii. The major iridoid glycoside was plantarenaloside and no aucubin type iridoids were found. This contrasted with a previous analysis of P. teucrioides, from the same Penstemon subsection, which was dominated by aucubin derivatives. PMID:7669280

Ismail, L D; el-Azizi, M M; Khalifa, T I; Stermitz, F R

1995-08-01

123

Trans-fused iridoid glycosides from Penstemon mucronatus.  

PubMed

Two new trans-fused iridoid glycosides (5 alpha H)-6 alpha-8-epidihydrocornin and (5 alpha H)-6 alpha-8-hydroxy-8-epiloganin, were isolated from Penstemon mucronatus, along with cornin, penstemoside and three hastatosides. The trans-fused iridoids are only the second and third known among over 900 described cis-fused iridoid glycosides. Two pairs of iridoids, identical except for the stereochemistry at C-8, were found. Structures were determined by spectroscopic methods. PMID:9887533

Krull, R E; Stermitz, F R

1998-12-01

124

Stability of steviol glycosides in several food matrices.  

PubMed

As steviol glycosides are now allowed as a food additive in the European market, it is important to assess the stability of these steviol glycosides after they have been added to different food matrices. We analyzed and tested the stability of steviol glycosides in semiskimmed milk, soy drink, fermented milk drink, ice cream, full-fat and skimmed set yogurt, dry biscuits, and jam. The fat was removed by centrifugation from the dairy and soy drink samples. Proteins were precipitated by the addition of acetonitrile and also removed by centrifugation. Samples of jam were extracted with water. Dry biscuits were extracted with ethanol. The resulting samples were concentrated with solid-phase extraction and analyzed by high-performance liquid chromatography on a C18 stationary phase and a gradient of acetonitrile/aqueous 25 mM phosphoric acid. The accuracy was checked using a standard addition on some samples. For assessing the stability of the steviol glycosides, samples were stored in conditions relevant to each food matrix and analyzed periodically. The results indicate that steviol glycosides can be analyzed with good precision and accuracy in these food categories. The recovery was between 96 and 103%. The method was also validated by standard addition, which showed excellent agreement with the external calibration curve. No sign of decomposition of steviol glycosides was found in any of the samples. PMID:23020306

Jooken, Etienne; Amery, Ruis; Struyf, Tom; Duquenne, Barbara; Geuns, Jan; Meesschaert, Boudewijn

2012-10-24

125

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. PMID:23533533

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

2013-01-01

126

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

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. PMID:23533533

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

2013-01-01

127

Functional annotation of expressed sequence tags as a tool to understand the molecular mechanism controlling flower bud development in tree peony.  

PubMed

Tree peony (Paeonia suffruticosaAndrews) is an important medicinal and ornamental plant. In China, its root bark is an important ingredient for traditional Chinese medicine. It is valued as an ornamental plant because its flower shows a wide variation in shape and color. We used flower buds at different developmental stages to construct the first cDNA library for this organism. A total of 2241 raw expressed sequence tags (ESTs) were obtained after unidirectional sequencing. After processing and assembly, they resulted in a total of 1300 unigenes [363 contigs with an average size of 3.5 ESTs (ranging from 2 up to 36) and 937 singletons]. Gene Ontology categories were assigned and further summarized into 13 broad families with biological roles according to similar functional characteristics or cellular roles. A total of 185 single nucleotide polymorphisms were detected for all contigs. We were able to detect open reading frames in the consensus sequences of 1268 unigenes. 97.5% of the ESTs showed significant similarity to sequences present in public databases. One hundred and sixty-seven short sequence repeats were obtained in the whole data set. All the analysis and information will be valuable resources for a better understanding of this important plant and also can be used for functional study in Paeoniaceae. PMID:19292824

Shu, Qing Y; Wischnitzki, Elisabeth; Liu, Zheng A; Ren, Hong X; Han, Xiao Y; Hao, Qing; Gao, Fen F; Xu, Su X; Wang, Liang S

2009-04-01

128

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 PMID:7624325

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

1995-01-01

129

Diterpene glycosides and polyketides from Xylotumulus gibbisporus.  

PubMed

Four new tetracyclic diterpene glycosides, namely, sordarins C-F (1-4), and three new ?-lactone polyketides, namely, xylogiblactones A-C (5-7), along with sordarin were isolated from the ethyl acetate extracts of the fermented broths of Xylotumulus gibbisporus YMJ863. The structures of 1-7 were elucidated on the basis of spectroscopic data analyses. The configurations of 1-4 were deduced by NOESY, molecular modeling, and comparison with the literature. The relative configurations of 5-7 were deduced by X-ray crystallographic analysis of 5. Compounds 1-5 and sordarin were evaluated in an antifungal assay using Candida albicans ATCC 18804, C. albicans ATCC MYA-2876, and Saccharomyces cerevisiae ATCC 2345, and only sordarin exhibited significant antifungal activities against these fungal strains, with MIC values of 64.0, 32.0, and 32.0 ?g/mL, respectively. The effect of compounds 1-7 and sordarin on the inhibition of NO production in lipopolysaccharide-activated murine macrophages was also evaluated. Compounds 2 and sordarin inhibited NO production with IC50 values of 327.2±46.6 and 157.1±24.1 ?M, respectively. PMID:24597849

Chang, Ya-Chih; Lu, Chung-Kuang; Chiang, Yin-Ru; Wang, Guei-Jane; Ju, Yu-Ming; Kuo, Yueh-Hsiung; Lee, Tzong-Huei

2014-04-25

130

Trial watch: Cardiac glycosides and cancer therapy.  

PubMed

Cardiac glycosides (CGs) are natural compounds sharing the ability to operate as potent inhibitors of the plasma membrane Na(+)/K(+)-ATPase, hence promoting-via an indirect mechanism-the intracellular accumulation of Ca(2+) ions. In cardiomyocytes, increased intracellular Ca(2+) concentrations exert prominent positive inotropic effects, that is, they increase myocardial contractility. Owing to this feature, two CGs, namely digoxin and digitoxin, have extensively been used in the past for the treatment of several cardiac conditions, including distinct types of arrhythmia as well as contractility disorders. Nowadays, digoxin is approved by the FDA and indicated for the treatment of congestive heart failure, atrial fibrillation and atrial flutter with rapid ventricular response, whereas the use of digitoxin has been discontinued in several Western countries. Recently, CGs have been suggested to exert potent antineoplastic effects, notably as they appear to increase the immunogenicity of dying cancer cells. In this Trial Watch, we summarize the mechanisms that underpin the unsuspected anticancer potential of CGs and discuss the progress of clinical studies that have evaluated/are evaluating the safety and efficacy of CGs for oncological indications. PMID:23525565

Menger, Laurie; Vacchelli, Erika; Kepp, Oliver; Eggermont, Alexander; Tartour, Eric; Zitvogel, Laurence; Kroemer, Guido; Galluzzi, Lorenzo

2013-02-01

131

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

PubMed

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

Prakash, Indra; Chaturvedula, Venkata Sai Prakash

2014-01-01

132

Probing the Influence of Protecting Groups on the Anomeric Equilibrium in Sialic Acid Glycosides with the Persistent Radical Effect  

PubMed Central

A method for the investigation of the influence of protecting groups on the anomeric equilibrium in the sialic acid glycosides has been developed on the basis of the equilibration of O-sialyl hydroxylamines by reversible homolytic scission of the glycosidic bond following the dictates of the Fischer–Ingold persistent radical effect. It is found that a trans-fused 4O,5N-oxazolidinone group stabilizes the equatorial glycoside, i.e., reduces the anomeric effect, when compared to the 4O,5N-diacetyl protected systems. This effect is discussed in terms of the powerful electron-withdrawing nature of the oxazolidinone system, which in turn is a function of its strong dipole moment in the mean plane of the pyranose ring system. The new equilibration method displays a small solvent effect and is most pronounced in less polar media consistent with the anomeric effect in general. The unusual (for anomeric radicals) poor kinetic selectivity of anomeric sialyl radicals is discussed in terms of the planar ?-type structure of these radicals and of competing 1,3-diaxial interactions in the diastereomeric transition states for trapping on the ?- and ?-faces of the radical. PMID:24606062

2015-01-01

133

Glycosidations of 2-deoxy glycosyl dithiophosphates using a tagged iodine(III)-promoter for simple purification.  

PubMed

The preparation of the 4-i-butylsulfonate derivative of the Zefirov reagent (5) and its use in a novel purification strategy for iodine(III)-promoted glycosidations of 2-deoxy diethyldithiophosphate glycosides is described. PMID:18292881

Kunst, Eike; Gallier, Florian; Dujardin, Gilles; Kirschning, Andreas

2008-03-01

134

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

PubMed Central

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

Yuan, Jun–hui; Cheng, Fang–Yun; Zhou, Shi–Liang

2012-01-01

135

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

PubMed

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

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

2015-04-20

136

Glycosides of polyenoic branched fatty acids from myxomycetes.  

PubMed

The determination of chemical structures of five novel compounds, i.e. one multibranched polyunsaturated fatty acid ((2E,4E,7S,8E,10E,12E,14S)-7,9,13,17-tetramethyl-7,14-dihydroxy-2,4,8,10,12,16-octadecahexaenoic acid) and its four glycosides from seven different myxomycetes is described. The absolute configuration of both hydroxyl groups was determined. The glycosides containing glucose, mannose and rhamnose. These compounds were identified by means of 1H and 13C NMR, MS, UV and IR spectra. Three of them were identified in Arcyria cinerea (Bull.) Pers., two in A. denudata (L.) Wetts., and A. nutans (Bull.) Grev., Fuligo septica (L.) Wigg., Lycogala epidendrum (L.) Fries, Physarum polycephalum Schwein., and Trichia varia Pers. contained one of the identified glycosides each. PMID:12126712

Rezanka, Tomás

2002-07-01

137

Synthesis and photosensitivity of isoxazolin-5-one glycosides.  

PubMed

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

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

2015-03-18

138

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

PubMed

Isolation and characterization of the new iridoid 10-hydroxy-(5 alpha H)-6-epidihydrocornin from Penstemon secundiflorus (Scrophulariaceae) is described. In biosynthetic experiments, deoxyloganic acid was incorporated into the trans-fused iridoid glycosides (5 alpha H)-6-epidihydrocornin and 10-hydroxy-(5 alpha H)-6-epidihydrocornin in P. secundiflorus. Formation of the trans-fused compounds is therefore a late event in the biosynthesis and does not occur during iridoid formation by cyclization of the open chain monoterpene precursor. In the same plant, 8-epideoxyloganic acid was not incorporated into the trans-iridoids. Deoxyloganic acid was also incorporated into 10-hydroxyhastatoside (which bears an 8 beta-methyl group), while 8-epideoxyloganic acid was incorporated into penstemoside (with an 8 alpha-methyl group). Thus, iridoid biosynthetic pathways leading from both deoxyloganic acid and 8-epideoxyloganic acid were found in the same plant. PMID:9862136

Krull, R E; Stermitz, F R; Franzyk, H; Jensen, S R

1998-11-01

139

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

140

Bufadienolide and spirostanol glycosides from the rhizomes of helleborusorientalis.  

PubMed

The rhizomes of Helleborus orientalis have been analyzed for the bufadienolide glycoside and spirostanol saponin constituents, resulting in the isolation of a new bufadienolide rhamnoside (1), along with two known bufadienolide glycosides (2 and 3) and five new spirostanol saponins (4-8). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against cultured tumor and normal cells. PMID:12608856

Watanabe, Kazuki; Mimaki, Yoshihiro; Sakagami, Hiroshi; Sashida, Yutaka

2003-02-01

141

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

142

New anthraquinone glycosides from the roots of Morinda citrifolia  

Microsoft Academic Search

Six new anthraquinone glycosides: digiferruginol-1-methylether-11-O-?-gentiobioside (1); digiferruginol-11-O-?-primeveroside (2); damnacanthol-11-O-?-primeveroside (3); 1-methoxy-2-primeverosyloxymethyl-anthraquinone-3-olate (4); 1-hydroxy-2-primeverosyloxymethyl-anthraquinone-3-olate (5); and 1-hydroxy-5,6-dimethoxy-2-methyl-7-primeverosyloxyanthraquinone (6) were isolated from Morinda citrifolia (Rubiaceae) roots together with four known anthraquinone glycosides. The structures of the new compounds were established using spectral methods. For five of the new compounds, the sugar is attached via the hydroxymethyl group of the anthraquinone C-2 carbon.

Kohei Kamiya; Wakako Hamabe; Shogo Tokuyama; Toshiko Satake

2009-01-01

143

New antifeedant triterpene glycosides from the Caribbean sponge Erylus formosus.  

PubMed

Two groups of antifeedant triterpene glycosides were identified from the Caribbean sponge Erylus formosus. The structure of formoside B, a novel N-acetyl amino derivative of the known penasterol tetrasaccharide formoside, was elucidated using NMR and mass spectral data. Four triterpene hexasaccharides and two triterpene trisaccharides, characterized by a 31-carbon aglycone, proved difficult to isolate and therefore only the structure of their aglycone was determined. Gas chromatographic analysis of derivatized saccharides from these mixtures established the carbohydrate content of these compounds. All of the triterpene glycosides isolated contributed to the chemical defenses of this sponge, although with differing activities. PMID:11833623

Kubanek, J; Fenical, W; Pawlik, J R

2001-01-01

144

New flavonol glycosides from the leaves of Caragana brachyantha.  

PubMed

Two new flavonol glycosides, brachysides C and D, together with three known flavonol glycosides, were isolated from the leaves of Caragana brachyantha. The structures of brachysides C and D were elucidated on the basis of detailed spectroscopic analysis as quercetin 5-O-[?-l-rhamnopyranosyl-(1 ? 6)-?-d-glucopyranoside]-7-O-[?-l-rhamnopyranoside] and quercetin 5-O-[?-l-rhamnopyranosyl-(1 ? 6)-?-d-glucopyranoside]-7-O-[?-l-rhamnopyranoside]-4'-O-[?-l-rhamnopyranoside], respectively. The presence of flavonol tetra- and triglycosides bearing a sugar moiety at position 5 was the first report from this genus Caragana. PMID:25422102

Perveen, Shagufta; Al-Taweel, Areej Mohammad; Al-Musayeib, Nawal; Fawzy, Ghada Ahmed; Khan, Afsar; Mehmood, Rashad; Malik, Abdul

2015-04-01

145

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

146

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.

147

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

Microsoft Academic Search

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

Derya Gülcemal; Özgen Alanku?-Çal??kan; Canan Karaalp; Ahmet Uygar Örs; Petek Ballar; Erdal Bedir

2010-01-01

148

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/ PMID:21622642

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

2011-01-01

149

A new phenylpropanoid glycoside from Jasminum subtriplinerve Blume.  

PubMed

From the ethyl acetate extract of the aerial parts of Jasminum subtriplinerve Blume (Oleaceae), 6'-O-menthiafoloylverbascoside (1), rutin (2), isoverbascoside (4), isooleoverbascoside (6), apiosylverbascoside (7), astragalin (9), isoquercitrin (10), and verbascoside (11) were isolated. Their structures were elucidated by extensive MS and NMR spectroscopy. Amongst 6'-O-menthiafoloylverbascoside (1) is a new phenylpropanoid glycoside. PMID:19031243

Huong, Nguyen Thi Hong; Cu, Nguyen Khac Quynh; Quy, Trinh Van; Zidorn, Christian; Ganzera, Markus; Stuppner, Hermann

2008-01-01

150

A new phenylpropanoid glycoside from Jasminum subtriplinerve Blume  

Microsoft Academic Search

From the ethyl acetate extract of the aerial parts of Jasminum subtriplinerve Blume (Oleaceae), 6?-O-menthiafoloylverbascoside (1), rutin (2), isoverbascoside (4), isooleoverbascoside (6), apiosylverbascoside (7), astragalin (9), isoquercitrin (10), and verbascoside (11) were isolated. Their structures were elucidated by extensive MS and NMR spectroscopy. Amongst 6?-O-menthiafoloylverbascoside (1) is a new phenylpropanoid glycoside.

Nguyen Thi Hong Huong; Nguyen Khac Quynh Cu; Trinh Van Quy; Christian Zidorn; Markus Ganzera; Hermann Stuppner

2008-01-01

151

Flavones and flavonol glycosides from Eupatorium cannabinum L  

Microsoft Academic Search

The 6-methoxyflavones hispidulin and eupafolin have been identified for the first time from the aerial parts ofEupatorium cannabinum L. The presence of the previously known flavonol glycosides astragalin, kaempferol-3-rutinoside, hyperoside, isoquercitrin and rutin could be confirmed. Hispidulin, eupafolin and rutin were screened for cytotoxicityin vitro.

E. T. Elema; J. Schripsema; T. M. Malingré

1989-01-01

152

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

153

An arrhythmic-inducing glycoside from Albizzia julibrissin Durazz, IV.  

PubMed

Three pyridoxine derivatives have been isolated from the fresh stem bark of Albizzia julibrissin DURAZZ.. One of them, named julibrin II, was found to exhibit arrhythmic-inducing action. However, neither the others having the same aglycone nor some glycosides having the same sugar unit showed the action. PMID:1611699

Higuchi, H; Kinjo, J; Nohara, T

1992-03-01

154

Phenolic glycosides from the stem bark of Albizzia julibrissin.  

PubMed

From the stem bark of Albizzia julibrissin DURAZZ (Leguminosae), two new phenolic glycosides (albibrissinosides A and B) were isolated. Their structures were determined by spectroscopic analysis. The albibrissinoside B was found to be a radical scavenger on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. PMID:15577257

Jung, Mee Jung; Kang, Sam Sik; Jung, Yu Jung; Choi, Jae Sue

2004-12-01

155

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

156

Apigenin glycosides from the flowers of Bellis perennis L.  

PubMed

Two next apigenin glycosides, apigenin 7-O-beta-D-glucuronide [III], apigenin 7-O-beta-D-glucoside [IV] were isolated from the flowers of Bellis perennis L. Their structures were determined by means of chemical and spectroscopic methods. PMID:10934792

Nazaruk, J; Gudej, J

2000-01-01

157

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

158

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

159

Quantitative HPLC analysis of cardiac glycosides in Digitalis purpurea leaves.  

PubMed

An analytical method for the determination of cardiac glycosides in Digitalis purpurea leaves by hplc was developed. Quantitation was carried out by the incorporation of lanatoside A as an internal standard. The present method is sufficiently precise and relatively simple. PMID:7673934

Ikeda, Y; Fujii, Y; Nakaya, I; Yamazaki, M

1995-06-01

160

[Qualitative and Quantitative HPLC-Analysis of Cardiac Glycosides].  

PubMed

An analytical pathway for identification of cardenolides from Adonis, Convallaria, Strophanthus and Lophopetalum extracts by HPLC is described. Structure-retention-relationships between cardiac glycosides and HPLC-separations of Strophanthus gratus, Strophanthus kombé and Adonis vernalis drugs are discussed. PMID:17396914

Tittel, G; Habermeier, H; Wagner, H

1982-08-01

161

Functional genomic analysis of Arabidopsis thaliana glycoside hydrolase family 1  

Microsoft Academic Search

In plants, Glycoside Hydrolase (GH) Family 1 ß-glycosidases are believed to play important roles in many diverse processes including chemical defense against herbivory, lignification, hydrolysis of cell wall-derived oligosaccharides during germination, and control of active phytohormone levels. Completion of the Arabidopsis thalianagenome sequencing project has enabled us, for the first time, to determine the total number of Family 1 members

Zhiwei Xu; Luis Escamilla-Treviño; Lihui Zeng; Mallikarjun Lalgondar; David Bevan; Brenda Winkel; Ali Mohamed; Chi-Lien Cheng; Ming-Che Shih; Jonathan Poulton; Asim Esen

2004-01-01

162

Jalapinoside, a macrocyclic bisdesmoside from the resin glycosides of Ipomea purga, as a modulator of multidrug resistance in human cancer cells.  

PubMed

The first macrocyclic bisdesmoside resin glycoside, jalapinoside (4), was purified by preparative-scale recycling HPLC from the MeOH-soluble extracts of Ipomoea purga roots, the officinal jalap. Purgic acid C (3), a new glycosidic acid of ipurolic acid, was identified as 3-O-?-d-quinovopyranoside, 11-O-?-d-quinovopyranosyl-(1?2)-O-?-d-glucopyranosyl-(1?3)-O-[?-d-fucopyranosyl-(1?4)]-O-?-l-rhamnopyranosyl-(1?2)-O-?-d-glucopyranosyl-(1?2)-O-?-d-quinovopyranoside (3S,11S)-dihydroxytetradecanoic acid. The acylating residues of this core were acetic, (+)-(2S)-methylbutanoic, and dodecanoic acids. The site of lactonization was defined as C-3 of the second saccharide moiety. Reversal of multidrug resistance by this noncytotoxic compound was evaluated in vinblastine-resistant human breast carcinoma cells. PMID:25536852

Bautista, Elihú; Fragoso-Serrano, Mabel; Pereda-Miranda, Rogelio

2015-01-23

163

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

PubMed Central

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

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

2013-01-01

164

Five naphthalene glycosides from the roots of Rumex patientia.  

PubMed

Three novel and two known naphthalene glycosides were isolated from the roots of Rumex patientia L. (Polygonaceae). The structures of the new compounds were established, respectively as 2-acetyl-3-methyl-6-carboxy-1,8-dihydroxynaphthalene-8-O-beta-D-glucopyranoside, 4,4"-binaphthalene-8,8"-O,O-di-beta-D-glucopyranoside and 2-acetyl-3-methyl-1,8-dihydroxynaphthalene-8-O-beta-D-glucopyranosyl (1-->3) beta-D-glucopyranoside on the basis of spectral analysis. The other napthalene glycosides were determined as nepodin-8-O-beta-D-glucopyranoside and torachrysone-8-O-beta-D-glucopyranoside by comparison of their spectral data with those previously reported. PMID:11249109

Demirezer, O; Kuruüzüm, A; Bergere, I; Schiewe, H J; Zeeck, A

2001-02-01

165

Structures of the novel diterpene glycosides from Stevia rebaudiana.  

PubMed

From the commercial extract of the leaves of Stevia rebaudiana, two new diterpenoid glycosides were isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside, and dulcoside A. The structures of the two new compounds were identified as 13-[(2-O-6-deoxy-?-d-glucopyranosyl-?-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid ?-d-glucopyranosyl ester (1), and 13-[(2-O-6-deoxy-?-d-glucopyranosyl-3-O-?-d-glucopyranosyl-?-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid ?-d-glucopyranosyl ester (2), on the basis of extensive NMR and MS spectral data as well as chemical studies. PMID:21489412

Chaturvedula, Venkata Sai Prakash; Prakash, Indra

2011-06-01

166

Two minor diterpene glycosides from the leaves of Stevia rebaudiana.  

PubMed

Two new new diterpene glycosides, 13-[(2-O-(6-O-beta-D-glucopyranosyl)-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid beta-D-glucopyranosyl ester (1) and 13-[(2-O-beta-D-glucopyranosyl-3-O-beta-D-fructofuranosyl-beta-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid beta-D-glucopyranosyl ester (2) were isolated from the leaves of Stevia rebaudiana, along with the known steviol glycosides stevioside, rebaudiosides A-F and dulcoside A. The structures of the two new compounds were established on the basis of extensive 2D NMR (COSY, HSQC, and HMBC), MS and chemical studies. PMID:21425668

Chaturvedula, Venkata Sai Prakash; Rhea, Joshua; Milanowski, Dennis; Mocek, Ulla; Prakash, Indra

2011-02-01

167

Neolignans, lignans and glycoside from the fruits of Melia toosendan.  

PubMed

Four new neolignans, meliasendanins A-D (1-4), and a new glycoside, toosenoside A (5), together with ten known ones (6-15), were isolated from a n-BuOH partition of the fruits of Melia toosendan. Their structures were elucidated by analyses of extensive spectroscopic data and comparison of the NMR data with those reported previously. Meliasendanin A (1) was a rare neolignan containing isochroman moiety, and its absolute configuration was determined using a CD spectrum. Toosenoside A (5) was an unusual glycoside with a rare naturally occurring aglycone and its structure was confirmed by X-ray single crystal diffraction analysis. The antioxidant activity of the isolated neolignans and lignans was evaluated by ABTS radical-scavenging assay. Compounds 1 and 13 exhibited strong antioxidant activity, with IC?? values of 62.8 and 45.1 ?M, respectively. PMID:25250895

Wang, Lun; Li, Fu; Yang, Chun-Yan; Khan, Ashfaq-Ahmad; Liu, Xin; Wang, Ming-Kui

2014-12-01

168

Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.  

PubMed

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

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

2014-01-01

169

Chemical and enzymatic hydrolysis of anthraquinone glycosides from madder roots.  

PubMed

For the production of a commercially useful dye extract from madder, the glycoside ruberythric acid has to be hydrolysed to the aglycone alizarin which is the main dye component. An intrinsic problem is the simultaneous hydrolysis of the glycoside lucidin primeveroside to the unwanted mutagenic aglycone lucidin. Madder root was treated with strong acid, strong base or enzymes to convert ruberythric acid into alizarin and the anthraquinone compositions of the suspensions were analysed by HPLC. A cheap and easy method to hydrolyse ruberythric acid in madder root to alizarin without the formation of lucidin turned out to be the stirring of dried madder roots in water at room temperature for 90 min: this gave a suspension containing pseudopurpurin, munjistin, alizarin and nordamnacanthal. Native enzymes are responsible for the hydrolysis, after which lucidin is converted to nordamnacanthal by an endogenous oxidase. PMID:12793459

Derksen, Goverdina C H; Naayer, Martijn; van Beek, Teris A; Capelle, Anthony; Haaksman, Ingrid K; van Doren, Henk A; de Groot, Aede

2003-01-01

170

Two new norbisabolane sesquiterpenoid glycosides from Glochidion coccineum.  

PubMed

Two new norbisabolane sesquiterpenoid glycosides, glochicoccinosides A (1) and B (2), together with two known compounds, have been isolated from the rhizomes of Glochidion coccineum. Their structures were elucidated by the combination of 1D NMR, 2D NMR, and MS spectral analysis, as well as chemical evidence. Cytotoxic activities and the antioxidant effect of these compounds were evaluated, but none of them showed activity. PMID:18058374

Xiao, Hai-Tao; He, Hong-Ping; Peng, Jiao; Wang, Yue-Hu; Yang, Xian-Wen; Hu, Xu-Jia; Hao, Xiao-Yan; Hao, Xiao-Jiang

2008-01-01

171

Two glycosides from the stem bark of Tetracentron sinense.  

PubMed

Two glycosides, tetracentronsides A and B, were isolated from the stem bark of Tetracentron sinense Oliv., along with ten known compounds, beta-sitosterol, lupeol, betulinic acid, oleanolic acid, vanillic aldehyde, vanillic acid, maslinic acid, huazhongilexin, daucosterol and catechin. On the basis of spectral and chemical evidence, tetracentronside A and B were identified as 3,4,5-trimethoxyphenyl-O-6'-O-vanilloyl-beta-D-glucopyranoside and (8R, 8'R) 9-beta-D-glucopyranosyl dihydrocubebin, respectively. PMID:10820820

Yi, J H; Zhang, G L; Li, B G; Chen, Y Z

2000-04-01

172

Two antigenotoxic chalcone glycosides from Mentha longifolia subsp. longifolia.  

PubMed

Abstract Context: Mentha L. (Labiatae) species (mint) with their flavoring properties have been used in food industries for centuries. Besides they have a great importance in drug development and medicinal applications due to various bioactive compounds of several members of the genus. Objective: The aim of this study was to isolate bioactive compounds with antimutagenic potential by bio-guided fractionation and determine their structures by spectroscopic methods. Materials and methods: The structural elucidation of the isolated compounds was done based on spectroscopic methods, including MALDI-MS, UV, IR, and 2D NMR experiments, and the bio-guided fractionation process was done by using the Ames/Salmonella test system. Henceforth, solely genotoxic and antigenotoxic potential of the new compounds were also confirmed up to 2?µM/plate by using the same test system. Results: Two new chalcone glycosides: (?R)-?,3,2',6'-tetrahydroxy-4-methoxy-4'-O-rutinosyldihydrochalcone and (?R)-?,4,2',6'-tetrahydroxy-4'-O-rutinosyldihydrochalcone, were isolated from Mentha longifolia (L.) Hudson subsp. longifolia, together with known six flavonoid glycosides and one phenolic acid: apigenin-7-O-glucoside, luteolin-7-O-glucoside, apigenin-7-O-rutinoside, luteolin-7-O-rutinoside, apigenin-7-O-glucuronide, luteolin-7-O-glucuronide, rosmarinic acid. According to the antimutagenicity results, both new test compounds significantly inhibited the mutagenic activity of 9-aminoacridine in a dose-dependent manner at the tested concentrations from 0.8 to 2?µM/plate. (?R)-?,4,2',6'-Tetrahydroxy-4'-O-rutinosyldihydrochalcone showed the maximum inhibition rate as 75.94% at 2?µM/plate concentration. Conclusions: This is the first report that two new chalcone glycosides were isolated from Mentha longifolia subsp. longifolia and their antimutagenic potentials by using mutant bacterial tester strains. In conclusion, the two new chalcone glycosides showed a significant antigenotoxic effect on 9-aminoacridine-induced mutagenesis at tested concentrations. PMID:25429992

Guvenalp, Zuhal; Ozbek, Hilal; Karadayi, Mehmet; Gulluce, Medine; Kuruuzum-Uz, Ayse; Salih, Bekir; Demirezer, Omur

2014-11-28

173

Steric control of N-acetylgalactosamine in glycosidic bond formation  

Microsoft Academic Search

N-Acetylgalactosamine, protected with a 4,6-cyclic acetal followed by selective acylation at 3-OH, provides an excellent donor for the synthesis of ?-glycosides, particularly the cancer associated antigens such as Tn, TF, Sialyl-Tn and Sialyl-TF. This fast and efficient synthesis is easily adaptable for commercial production of mucin type glycopeptides with O-linked carbohydrate structures which are currently being investigated as vaccines against

John E. Yule; Ting C. Wong; Sham S. Gandhi; Dongxu Qiu; Marc A. Riopel; R. Rao Koganty

1995-01-01

174

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

175

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina  

Microsoft Academic Search

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

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

2009-01-01

176

Iridoid glycoside sequestration by two aposematic Penstemon -feeding geometrid larvae  

Microsoft Academic Search

The iridoid glycoside catalpol was found to be sequestered by larvae ofMeris alticola feeding onPenstemon virgatus and by larvae ofNeoterpes graefiaria which utilizeP. barbatus. The strikingly similar larval patterns of these two ennomine geometrids were previously considered to be disruptive, but predator-based Mullerian mimicry is equally likely to be involved. The cryptic adult moths generally contain only small amounts of

Frank R. Stermitz; Dale R. Gardner; Noel McFarland

1988-01-01

177

Minor diterpene glycosides from the leaves of Stevia rebaudiana.  

PubMed

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

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

2014-05-23

178

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

PubMed

Ten acylated flavonol glycosides were isolated from aqueous acetone extracts of the aerial parts of the forage legume, Onobrychis viciifolia, and their structures determined using spectroscopic methods. Among these were eight previously unreported examples which comprised either feruloylated or sinapoylated derivatives of 3-O-di- and 3-O-triglycosides of kaempferol (3,5,7,4'-tetrahydroxyflavone) or quercetin (3,5,7,3',4'-pentahydroxyflavone). The diglycosides were acylated at the primary Glc residue of O-?-Rhap(1?6)-?-Glcp (rutinose), whereas the triglycosides were acylated at the terminal Rha residues of the branched trisaccharides, O-?-Rhap(1?2)[?-Rhap(1?6)]-?-Galp or O-?-Rhap(1?2)[?-Rhap(1?6)]-?-Glcp. Identification of the primary 3-O-linked hexose residues as either Gal or Glc was carried out by negative ion electrospray and serial MS, and cryoprobe NMR spectroscopy. Analysis of UV and MS spectra of the acylated flavonol glycosides provided additional diagnostic features relevant to direct characterisation of these compounds in hyphenated analyses. Quantitative analysis of the acylated flavonol glycosides present in different aerial parts of sainfoin revealed that the highest concentrations were in mature leaflets. PMID:21292287

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

2011-04-01

179

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

2010-01-01

180

A comparison of flavonoid glycosides by electrospray tandem mass spectrometry  

NASA Astrophysics Data System (ADS)

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

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

2006-01-01

181

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. PMID:21467581

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

2011-01-01

182

Immunomodulatory action of triterpene glycosides isolated from the sea cucumber Actinocucumis typica. Structure-activity relationships.  

PubMed

Stimulation of lysosomal activity and ROS formation in mouse peritoneal macrophages by five triterpene glycosides, typicosides A1 (1), A2 (2), B1 (3), C1 (4) and C2 (5) has been studied and compared with their cytotoxic activities. Glycosides 1-3 possess moderate activities, but the most cytotoxic glycoside 5 is not active. Typicoside C1 (4), with low toxicity, was proved to be the most active concerning stimulation of ROS formation. This is the first example of a triterpene glycoside from sea cucumbers with low cytotoxicity, but which demonstrates a strong immunostimulatory effect on mouse peritoneal macrophages in vitro. PMID:25115075

Pislyagin, Evgeny A; Aminin, Dmitry L; Silchenko, Alexandra S; Avilov, Sergey A; Andryjashchenko, Pelageya V; Kalinin, Vladimir I; Padmakumar, Krishna

2014-06-01

183

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. PMID:23015769

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

2012-01-01

184

Herbivore avoidance of digitalis extracts is not mediated by cardiac glycosides.  

PubMed

This study was conducted to determine whether avoidance of digitalis (Digitalis purpurea) by mountain beaver (Aplodontia rufa) is induced by toxic cardiac glycosides. High-performance liquid chromatography and behavioral assays were used to relate animal responses with the presence of common cardiac glycosides in several digitalis extracts. Statistical analyses of multiple-choice tests showed no correlation between cardiac glycoside content and mountain beaver avoidance of apple cubes treated with digitalis extracts. Therefore, we concluded that known toxic cardiac glycosides were not responsible for chemosensory cues that inhibited intake of food treated with digitalis extracts. These results suggest that digitalis is a source of an effective nontoxic herbivore repellent. PMID:24233675

Nolte, D L; Kelly, K L; Kimball, B A; Johnston, J J

1995-10-01

185

Reversible Sterilization  

ERIC Educational Resources Information Center

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

Largey, Gale

1977-01-01

186

Separation and characterization of soluble esterified and glycoside-bound phenolic compounds in dry-blanched peanut skins by liquid chromatography-electrospray ionization mass spectrometry.  

PubMed

A large variety of soluble phenolic compounds, including phenolic acids (hydroxybenzoic acids, ethyl protocatechuate, and hydroxycinnamic acids, as well as phenylacetic acid and phenyllactic acid), stilbenes (trans-piceatannol and trans-3,3',5,5'-tetrahydroxy-4'-methoxystilbene), flavan-3-ols (e.g., (-)-epicatechin, (+)-catechin, (-)-epiafzelechin, and their polymers (the proanthocyanidins, PACs)), other flavonoids (e.g., isoflavones, flavanols, and flavones), and biflavonoids, were released from esters and glycosides by base/acid hydrolysis and identified in acetonic extracts of dry-blanched peanut skins (PS). Reversed-phase high-performance liquid chromatography (RP-HPLC) coupled with electrospray ionization mass spectrometry (ESI-MS(n)) was applied to separate and identify the phenolic constituents. Tentative identification of the separated phenolics was based on molecular ions and MS(n) fragmentation patterns acquired by ESI-MS in the negative-ion mode. Identification of free phenolic acids, stilbenes, and flavonoids was also achieved by commercial standards and by published literature data. Quantification was performed on the basis of peak areas of the UV signals from the HPLC chromatograms and calibration curves of the commercial standards. The flavonoids of PS exist mostly in glycoside-bound forms, but the aglycones can be liberated upon acid hydrolysis. PS contain significantly more PACs compared to free phenolic compounds: PAC monomers to tetramers constituted 92.0% of esterified phenolic compounds. The PAC monomer ((+)-catechin) and dimers are the main phenolics released from glycosides and account for 31.7 and 59.1%, respectively, of the total glycoside-bound phenolic compounds. PMID:25354220

Ma, Yuanyuan; Kosi?ska-Cagnazzo, Agnieszka; Kerr, William L; Amarowicz, Ryszard; Swanson, Ruthann B; Pegg, Ronald B

2014-11-26

187

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

188

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

189

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. PMID:22438657

Liao, Haibing; Liu, Huixin; Yuan, Ke

2012-01-01

190

[Effect of plant glycosides on resistance and capacitance vessels].  

PubMed

In the anaesthetized cat, SCOA ( Miroton ), a product which contains extracts from Scilla , Convallaria , Oleander and Adonis , displays not only its well-known positive inotropic effect but has also constrictor effects on veins when applied in intravenous doses of 21.5-100 GPU /kg ( GPU = guinea-pig units, i.e. cardiotoxic equivalents related to 1 g body weight of guinea-pigs). The latter effect differs in that it is somewhat more prolonged. With intraduodenal administration the doses required to achieve equal peak effects as with intravenous injection are about 4 times larger and this suggests a relatively good enteral availability in the cat. SCOA constricts not only veins but also arteries. However, this latter effect is comparatively small and occurs only after intraarterial infusion of high doses (9.1 and 91 GPU /min, respectively).--The cardiac glycosides contained in the drug product primarily account for its vasoactive qualities. The venous constrictor effect correlates with the guinea-pig units. In qualitative respects, the pure glycosides cymarin , convallatoxin , proscillaridin , and scillaren exert equal effects. There is, however, evidence that the correlation between the effect on veins and on the heart differs for the glycosides tested. Based on equal guinea-pig units, the adonis extract, for instance, acts on capacitance vessels about twice as much as scilla , oleander and convallaria extracts. Cymarin , too, has a stronger effect on veins than would be expected from its cardiotoxic effect. The action on arteries and veins are based on different mechanism.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:6540100

Lehmann, H D

1984-01-01

191

[New flavonoid-glycosides from Crataegus monogyna and Crataegus pentagyna].  

PubMed

From the leaves and flowers of Crataegus monogyna and C. Pentagyna six new flavonoid-C- and O-glycosides respectively have been isolated and identified as 2''-O-rhamnosyl-orientin, 2''-O-rhamnosyl-isoorientin, 2''-O-rhamnosyl-isovitexin, rutin, spiraeosid, 8-methoxy-kämpferol and 8-methoxy-kämpferol-3-O-glucoside. The structure of O-rhamnosyl-vitexin and O-acetyl-O-rhamnosyl-vitexin isolated previously, have been elucidated unambigiously mainly by NMR- and MS-spectroscopy. PMID:17402083

Nikolov, N; Seligmann, O; Wagner, H; Horowitz, R M; Gentili, B

1982-01-01

192

Secoiridoid glycosides and an antifungal anthranilate derivative from Gentiana tibetica.  

PubMed

Repetitive chromatography of the methanol extract of the roots of Gentiana tibetica afforded two new secoiridoid glycosides and a novel antifungal anthranilic acid derivative, together with beta-sitosterol, daucosterol, oleanolic acid, loganic acid, gentiopicroside, sweroside, 2'-(2,3-dihydroxybenzoyl)sweroside, trifloroside, rindoside and macrophylloside A. The structures of the new products were determined mainly by spectroscopic methods as 8-hydroxy-10-hydrosweroside, isomacrophylloside and ethyl N-docosanoylanthranilate. Ethyl N-docosanoylanthranilate inhibited the growth of the human pathogenic fungi Candida albicans and Aspergillus flavus. The taxonomic significance of the constituent is discussed briefly. PMID:9611826

Tan, R X; Kong, L D; Wei, H X

1998-04-01

193

FLAVONOL GLYCOSIDES FROM THE NATIVE AMERICAN PLANT GAURA LONGIFLORA  

PubMed Central

Phytochemical investigation of the native American plant Gaura longiflora led to the isolation of three new and eight known flavonol glycosides. The structures of the new compounds were established primarily by spectroscopic data as quercetin 3-O-(2?-O-?-l-rhamnopyranosyl-6?-O-E-p-coumaroyl)-?-D-glucopyranoside (1), kaempferol 3-O-(2?-O-?-l-rhamnopyranosyl-6?-O-E-p-coumaroyl)-?-d-gluco-pyranoside (2) and quercetin 3-O-(2?-O-?-l-rhamnopyranosyl-6?-O-Z-p-coumaroyl)-?-D-glucopyrano-side (3). PMID:24371369

Xu, Wen-Hui; Jacob, Melissa R.; Agarwal, Ameeta K.; Clark, Alice M.; Liang, Zong-Suo; Li, Xing-Cong

2013-01-01

194

[Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum].  

PubMed

The study on the buds of Jasminum officinale L. var. grandiflorum was carried out to look for anti-HBV constituents. The isolation and purification were performed by HPLC and chromatography on silica gel, polyamide and Sephadex LH-20 column. The structures were elucidated on the basis of physicochemical properties and spectral analysis. Six iridoid glycosides were identified as jasgranoside B (1), 6-O-methy-catalpol (2), deacetyl asperulosidic acid (3), aucubin (4), 8-dehydroxy shanzhiside (5), and loganin (6). Jasgranoside B (1) is a new compound. Compounds 2-6 were isolated from Jasminum officinale L. var. grandiflorum for the first time. PMID:22242454

Zhao, Gui-qin; Yin, Zhi-feng; Liu, Yu-cui; Li, Hong-bo

2011-10-01

195

Additional new minor cucurbitane glycosides from Siraitia grosvenorii.  

PubMed

Continuous phytochemical studies of the crude extract of Luo Han Guo (Siraitia grosvenorii) furnished three additional new cucurbitane triterpene glycosides, namely 11-deoxymogroside V, 11-deoxyisomogroside V, and 11-deoxymogroside VI. The structures of all the isolated compounds were characterized on the basis of extensive NMR and mass spectral data as well as hydrolysis studies. The complete ¹H- and ¹³C-NMR spectral assignments of the three unknown compounds are reported for the first time based on COSY, TOCSY, HSQC, and HMBC spectroscopic data. PMID:24662081

Prakash, Indra; Chaturvedula, Venkata Sai Prakash

2014-01-01

196

Two new glycosides from the fruits of Morinda citrifolia L.  

PubMed

To study the chemical constituents of the fruits of noni (Morinda citrifolia L.), and find novel compounds, an n-butanol extract of the ethanol soluble fraction was subjected to repeated silica gel and ODS column chromatography and HPLC. Two new glycosides were isolated and their structures elucidated by NMR and HRFAB-MS spectrometry as (2E,4E,7Z)-deca-2,4,7-trienoate-2-O-?-D-glucopyranosyl-?-D-glucopyranoside and amyl-1-O-?-D-apio-furanosyl-1,6-O-?-D-glucopyranoside, respectively. PMID:23103531

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

2012-01-01

197

Acylated flavonol glycosides from the flower of Inula britannica.  

PubMed

Three new acylated flavonol glycosides, patuletin 7-O-(6' '-isobutyryl)glucoside (1), patuletin 7-O-[6' '-(2-methylbutyryl)]glucoside (2), and patuletin 7-O-(6' '-isovaleryl)glucoside (3), were isolated from the n-BuOH extract of Inula britannica flowers by bioassay-guided fractionation, together with other known flavonoids. The structures were elucidated by 1D and 2D NMR, FABMS, and other spectral analyses. The eight flavonoids, including new compounds (1-3), patulitrin (7), nepitrin (8), axillarin (10), patuletin (11), and luteolin (12), showed profound antioxidant activity in DPPH assay and cytochrome-c reduction assay using HL-60 cell culture system. PMID:10650074

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

2000-01-01

198

Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors.  

PubMed

Bibenzyl glycosides 1-6 were synthesized from 2,4-dihydoxybenzaldehyde and xylose, glucose, cellobiose or maltose. The key steps in the synthesis were the Wittig reaction and trichloroacetimidate glycosylation. Tests for tyrosinase inhibitory activity showed that all were significantly active, indicating that they are unique hydrophilic tyrosinase inhibitors. Bibenzyl xyloside 2 is a particularly potent inhibitor (IC(50) = 0.43 ?M, 17 times higher than that of kojic acid). These results suggest that the hydrophilic cavity of tyrosinase might accommodate the bulky carbohydrate on the bibenzyl scaffold. PMID:21334791

Tajima, Reiko; Oozeki, Hiromi; Muraoka, Seiichi; Tanaka, Saori; Motegi, Yukari; Nihei, Hiroyuki; Yamada, Yoichi; Masuoka, Noriyoshi; Nihei, Ken-ichi

2011-04-01

199

New Lignans and Iridoid Glycosides from Dipsacus asper Wall.  

PubMed

Six new compounds, including four new lignans, dipsalignan A (1), B-D (3-5), and two new bis-iridoid glycoside dimmers, dipsanosides M (7) and N (8), together with two known compounds (2) and (6), have been isolated from the roots of Dipsacus asper Wall. Their structures were established on the basis of spectroscopic data (MS, 1D, 2D NMR, and CD) and chemical methods. All the isolated compounds were tested against human immunodeficiency virus-1 (HIV-1) integrase inhibition activities, and only compounds 1, 2, 7, and 8 displayed weak activities. PMID:25635380

Sun, Xinguang; Ma, Guoxu; Zhang, Dawei; Huang, Wenhua; Ding, Gang; Hu, Huagang; Tu, Guangzhong; Guo, Baolin

2015-01-01

200

Two new flavonoid glycosides from Artemisia frigida Willd  

Microsoft Academic Search

An investigation of the n-BuOH-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new flavonoid glycosides, named friginoside A and friginoside B. Their structures were characterized as 5,7-dihydroxy-3?,4?,5?-trimethoxy flavone 7-O-?-d-glucuronide (1) and 5,7-dihydroxy-3?,4?,5?-trimethoxyflavone 7-O-?-d-glucuronyl-(1 ? 2)O-?-d-glucuronide (2) on the basis of 1D and 2D NMR spectral analysis.

Qing-Hu Wang; Wu-Li-Ji Ao; Xiu-Lan Wang; Xiao-Hua Bao; Jin-Hui Wang

2010-01-01

201

Two new flavonoid glycosides from Artemisia frigida Willd.  

PubMed

An investigation of the n-BuOH-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new flavonoid glycosides, named friginoside A and friginoside B. Their structures were characterized as 5,7-dihydroxy-3',4',5'-trimethoxy flavone 7-O-?-d-glucuronide (1) and 5,7-dihydroxy-3',4',5'-trimethoxyflavone 7-O-?-d-glucuronyl-(1 ? 2)O-?-d-glucuronide (2) on the basis of 1D and 2D NMR spectral analysis. PMID:21061216

Wang, Qing-Hu; Ao, Wu-Li-Ji; Wang, Xiu-Lan; Bao, Xiao-Hua; Wang, Jin-Hui

2010-11-01

202

Vanicosides C-F, new phenylpropanoid glycosides from Polygonum pensylvanicum.  

PubMed

The isolation of the protein kinase C inhibitors, vanicoside A (1) and vanicoside B (2), from Polygonum pensylvanicum prompted continued interest in the active principles of this plant. A new, more efficient isolation procedure has been developed to facilitate separation of homologues of vanicosides A and B from the complex extract. Several new phenylpropanoid glycosides have since been isolated. The structures of these principles were determined to be 2'-O-acetylhydropiperoside (4), 6'-O-p-coumarylhydropiperoside (5), 4'-O-acetylvanicoside A (6), and 3'-O-acetylvanicoside B (7) using negative ion FABMS, 1H NMR, and 2D NMR techniques. PMID:9644060

Brown, L L; Larson, S R; Sneden, A T

1998-06-26

203

A new steroidal glycoside from the seeds of Hyoscyamus niger.  

PubMed

A new steroidal glycoside hyoscyamoside G (1), together with two known analogues hyoscyamoside E (2) and hyoscyamoside F1 (3), was isolated from the seeds of Hyoscyamus niger. The structure of 1 was established as (22R,24Z)-1?,3?,7?,22,26-pentakishydroxylergost-22-O-?-d-gulcopyranosyl-5,24-diene-26-O-?-d-glucopyranoside, by means of chemical and spectroscopic methods including HRESI-MS, 1D and 2D NMR. In vitro, compound 2 showed cytotoxicity against human lung cancer cell H460 with IC50 value of 66 ?g/mL. PMID:23745717

Zhang, Wenna; Zhang, Wei; Luo, Jianguang; Kong, Lingyi

2013-01-01

204

Carotenoid glycoside esters from the thermophilic bacterium meiothermusruber  

PubMed

The thermophilic bacterium Meiothermus ruber produces a series of carotenoid glycoside esters. The major carotenoid has been identified as 1'-beta-glucopyranosyl-3,4,3',4'-tetradehydro-1', 2'-dihydro-beta,psi-caroten-2-one (1). It is acylated at the 6' '-position of the glucose unit by a series of C10-C17 fatty acids. The structure of 1 was established by spectral means, including complete assignment of the 1H and 13C NMR resonances by inverse 2D NMR spectroscopy. These carotenoids are thought to play roles in stabilizing membranes of this thermophilic organism. PMID:10395503

Burgess; Barrow; Gao; Heard; Glenn

1999-06-01

205

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

PubMed

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

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

2011-06-01

206

Antiproliferative, Cytotoxic and Hemolytic Activities of a Triterpene Glycoside from Psolus patagonicus and Its Desulfated Analog  

Microsoft Academic Search

Background: The major triterpene glycoside of the sea cucumber Psolus patagonicus and its desulfated analog were tested for their antiproliferative, cytotoxic and hemolytic activities, and their effect on NF-?B activation. Methods: The antiproliferative action of glycosides 1 and 2 were determined on 3 tumor cell lines. Their effect on the activation of NF-?B was evaluated by indirect immunofluorescence assay staining

Valeria P. Careaga; Carlos Bueno; Claudia Muniain; Laura Alché; Marta S. Maier

2009-01-01

207

Fate of Host-Plant Iridoid Glycosides in Lepidopteran Larvae of Nymphalidae and Arcthdae  

Microsoft Academic Search

We compared the ability of larvae of six lepidopteran species to sequester iridoid glycosides. All larvae were fed on a common host plant, Plantago lanceolata, which contains two iridoid glycosides, aucubin and catalpol. Four species of arctiids were examined: Pyrrharctia isabella, Spilosoma congrua, Spilosoma latipennis, and Spilosoma virginica. For comparison, we also examined two nymphalid species, one of which, Junonia

M. Deane Bowers; Nancy E. Stamp

1997-01-01

208

Tyrosinase inhibition studies of cycloartane and cucurbitane glycosides and their structure–activity relationships  

Microsoft Academic Search

In the present paper, tyrosinase inhibition studies and structure–activity relationship of eight cycloartane glycosides and one cucurbitane glycoside and its genin, which were isolated from Astragalus (Leguminoseae) and Bryonia (Cucurbitaceae) plants, have been discussed. The activities are compared with two reference tyrosinase inhibitors, kojic acid and l-mimosine. These studies and the SAR showed that the askendoside B which exhibited highly

Mahmud Tareq Hassan Khan; M. Iqbal Choudhary; Atta-ur-Rahman; Reyhan P. Mamedova; Manzura A. Agzamova; Mukhlis N. Sultankhodzhaev; Mahamed I. Isaev

2006-01-01

209

Environment and Genotype Affect Sweetpotato Storage Root Periderm Resin Glycoside Content  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

210

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

PubMed

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

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

2003-02-01

211

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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 ann...

212

Glycosynthesis in a waterworld: new insight into the molecular basis of transglycosylation in retaining glycoside hydrolases.  

PubMed

Carbohydrates are ubiquitous in Nature and play vital roles in many biological systems. Therefore the synthesis of carbohydrate-based compounds is of considerable interest for both research and commercial purposes. However, carbohydrates are challenging, due to the large number of sugar subunits and the multiple ways in which these can be linked together. Therefore, to tackle the challenge of glycosynthesis, chemists are increasingly turning their attention towards enzymes, which are exquisitely adapted to the intricacy of these biomolecules. In Nature, glycosidic linkages are mainly synthesized by Leloir glycosyltransferases, but can result from the action of non-Leloir transglycosylases or phosphorylases. Advantageously for chemists, non-Leloir transglycosylases are glycoside hydrolases, enzymes that are readily available and exhibit a wide range of substrate specificities. Nevertheless, non-Leloir transglycosylases are unusual glycoside hydrolases in as much that they efficiently catalyse the formation of glycosidic bonds, whereas most glycoside hydrolases favour the mechanistically related hydrolysis reaction. Unfortunately, because non-Leloir transglycosylases are almost indistinguishable from their hydrolytic counterparts, it is unclear how these enzymes overcome the ubiquity of water, thus avoiding the hydrolytic reaction. Without this knowledge, it is impossible to rationally design non-Leloir transglycosylases using the vast diversity of glycoside hydrolases as protein templates. In this critical review, a careful analysis of literature data describing non-Leloir transglycosylases and their relationship to glycoside hydrolase counterparts is used to clarify the state of the art knowledge and to establish a new rational basis for the engineering of glycoside hydrolases. PMID:25793417

Bissaro, Bastien; Monsan, Pierre; Fauré, Régis; O'Donohue, Michael J

2015-04-01

213

Biochemical detoxication: mechanism of differential tiger swallowtail tolerance to phenolic glycosides  

Microsoft Academic Search

Phenolic glycosides, commonly occurring allelochemicals in the plant family Salicaceae, are differentially toxic to subspecies of the eastern tiger swallowtail and responsible for striking differences in the abilities of Papilio glaucus canadensis and P.g. glaucus to utilize the Salicaceae as food plants. This research was designed to test the hypothesis that particularly high esterase activity confers resistance to phenolic glycosides

R. L. Lindroth

1989-01-01

214

Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis.  

PubMed

Two new sulfated triterpene glycosides, philinopside E (1) and F (2), have been isolated from the sea cucumber Pentacta quadrangularis. Their structures have been established by extensive spectral analysis (NMR and MS) and chemical evidence. Glycoside 1 showed significant cytotoxicity (Ed(50) 0.75-3.50 microg mL(-1)) against ten tumor cell lines. PMID:16644536

Zhang, Shi-Long; Li, Ling; Yi, Yang-Hua; Sun, Peng

2006-04-01

215

Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.  

PubMed

The cardiac glycoside natural product digitoxin was selectively glycosylated at one of its five hydroxyl groups using a borinic acid derived catalyst. This method provided access to the glycosylation pattern characteristic of a subclass of natural products from Digitalis purpurea. Variation of the glycosyl donor was tolerated, enabling the synthesis of novel cardiac glycoside analogs from readily available materials. PMID:23465047

Beale, Thomas M; Taylor, Mark S

2013-03-15

216

Alkane1,2-diol-based glycosides and fatty glycosides and wax esters in Roseiflexus castenholzii and hot spring microbial mats  

Microsoft Academic Search

The lipid composition of Roseiflexus castenholzii, a thermophilic filamentous phototrophic bacterium related to uncultivated filamentous phototrophic bacteria that predominate in hot spring microbial mats, is reported. R. castenholzii lipid extracts were dominated by components characterized by alkane-1-ol-2-alkanoate moieties glycosidically bonded to a C6 sugar. Similar fatty glycosides, with an additional fatty acid esterified, were detected by HPLC-MS. R. castenholzii also

Stefan Schouten; Satoshi Hanada; Ellen C. Hopmans; Jaap S. Sinninghe Damsté; David M. Ward

2002-01-01

217

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

218

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

PubMed

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

Lampert, Evan C; Bowers, M Deane

2010-10-01

219

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

220

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. PMID:24327825

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

2013-01-01

221

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

222

Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria  

PubMed Central

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

2015-01-01

223

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. PMID:24970171

Trincone, Antonio

2013-01-01

224

DFT analysis of NMR scalar interactions across the glycosidic bond in DNA.  

PubMed

The relationship between the glycosidic torsion angle chi, the three-bond couplings (3)J(C2/4-H1') and (3)J(C6/8-H1'), and the one-bond coupling (1)J(C1'-H1') in deoxyribonucleosides and a number of uracil cyclo-nucleosides has been analyzed using density functional theory. The influence of the sugar pucker and the hydroxymethyl conformation has also been considered. The parameters of the Karplus relationships between the three-bond couplings and chi depend strongly on the aromatic base. (3)J(C2/4-H1') reveals different behavior for deoxyadenosine, deoxyguanosine, and deoxycytidine as compared to deoxythymidine and deoxyuridine. In the case of (3)J(C6/8-H1'), an opposite trans to cis ratio of couplings is obtained for pyrimidine nucleosides in contrast to purine nucleosides. The extremes of the Karplus curves are shifted by ca. 10 degrees with respect to syn and anti-periplanar orientations of the coupled nuclei. The change in the sugar pucker from S to N decreases (3)J(C2/4-H1') and (3)J(C6/8-H1'), while increasing (1)J(C1'-H1') for the syn rotamers, whereas all of the trends are reversed for the anti rotamers. The influence of the sugar pucker on (1)J(C1'-H1') is interpreted in terms of interactions between the n(O4'), sigma*(C1'-H1') orbitals. The (1)J(C1'-H1') are related to chi through a generalized Karplus relationship, which combines cos(chi) and cos(2)(chi) functions with mutually different phase shifts that implicitly accounts for a significant portion of the related sugar pucker effects. Most of theoretical (3)J(C2/4-H1') and (3)J(C6/8-H1') for uracil cyclo-nucleosides compare well with available experimental data. (3)J(C6/8-H1') couplings for all C2-bridged nucleosides are up to 3 Hz smaller than in the genuine nucleosides with the corresponding chi, revealing a nonlocal aspect of the spin-spin interactions across the glycosidic bond. Theoretical (1)J(C1'-H1') are underestimated with respect to the experiment by ca. 10% but reproduce the trends in (1)J(C1'-H1') vs chi. PMID:12643728

Munzarová, Markéta L; Sklenár, Vladimír

2003-03-26

225

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

226

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. PMID:24160332

2013-01-01

227

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.

228

Vasectomy reversal.  

PubMed

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

Belker, A M

1987-02-01

229

A comparison of sample preparation techniques for quantifying iridoid glycosides sequestered by lepidopteran larvae.  

PubMed

This study compared different methods of tissue preparation for extraction of iridoid glycosides sequestered by three species of lepidopteran larvae. Junonia coenia is a specialist on plant species that produce iridoid glycosides, while the arctiids Estigmene acrea and Spilosoma congrua are both polyphagous and will eat plants that produce iridoid glycosides. Larvae of all three species were reared on leaves of Plantago lanceolata, which produces two primary iridoid glycosides, aucubin and catalpol. Three methods of preparing the specimens before extraction in methanol were compared in all three species: 1) larvae were flash-frozen in liquid nitrogen, 2) larvae were macerated fresh in boiling methanol, or 3) larvae were macerated fresh in room temperature methanol. A set of J. coenia larvae was oven-dried before maceration as an additional treatment for this species only. Junonia coenia sequestered the most iridoid glycosides, while E. acrea sequestered the least, and S. congrua was intermediate. Estigmene acrea was poor at sequestering catalpol. Tissue preparation method only significantly influenced iridoid glycoside recovery from S. congrua, with maceration in room-temperature methanol being the most effective of the three methods. This study shows that treatment of insects prior to iridoid glycoside extraction can influence recovery of the compounds, and that the effects of treatment may vary among different species. PMID:21475987

Lampert, Evan C; Bowers, M Deane

2011-05-01

230

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. PMID:24023961

Guleria, Praveen; Yadav, Sudesh Kumar

2013-01-01

231

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

232

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

233

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

234

Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.  

PubMed

The organic soluble extract from the leaves of the native North American prairie plant Ipomoea leptophylla (big root morning glory) showed in vitro activity against M. tuberculosis. Bioassay-guided fractionation of this extract resulted in the identification of two new resin glycosides (6, 7). Base-catalyzed hydrolysis of these glycosides gave operculinic acid (1) as the glycosidic acid component as well as trans-cinnamic acid, propanoic acid, and lauric acid. The complete structure elucidation was accomplished through derivatization, 1D and 2D NMR spectroscopy (TOCSY, ROESY, HSQC, HMBC), and MS/MS experiments on 6 and 7 as well as the permethylated derivative 8. PMID:14640518

Barnes, Curtis C; Smalley, Mary K; Manfredi, Kirk P; Kindscher, Kelly; Loring, Hillary; Sheeley, Douglas M

2003-11-01

235

Steroidal glycosides from the underground parts of Yucca glauca and their cytotoxic activities.  

PubMed

Six steroidal glycosides and 14 known compounds were isolated from the underground parts of Yucca glauca (Agavaceae). Their structures were determined from extensive spectroscopic analysis, including analysis of two-dimensional NMR data, and from chemical transformations. The compounds were also evaluated for cytotoxic activities against HL-60 human leukemia cells and A549 human lung adenocarcinoma cells. Four spirostanol glycosides and three furostanol glycosides exhibited cytotoxic activities against both HL-60 and A549 cells. Two of the compounds induced apoptosis in HL-60 cells. PMID:24612536

Yokosuka, Akihito; Suzuki, Tomoka; Tatsuno, Satoru; Mimaki, Yoshihiro

2014-05-01

236

[Glycosides from flowers of Jasminum officinale L. var. grandiflorum].  

PubMed

To study the chemical constituents of the flower of Jasminum officinale L. var. grandiflorum. The compounds were isolated and purified by re-crystallization and chromatography on silica gel and Sephadex LH-20 column. Their structures were elucidated on the physicochemical properties and spectral analysis. Seven glycosides were identified as kaempferol-3-O-alpha-L-rhamnopyranosyl (1-->3)-[alpha-L-rhamnopyranosyl (1-->6)]-beta-D-galactopyranoside (I), kaempferol-3-O-rutinoside (II), 7-ketologanin (III), oleoside-11-methyl ester (IV), 7-glucosyl-l1-methyl oleoside (V), ligstroside (VI), oleuropein (VII). Compound I is a new compound. Compounds III and V were isolated from the family of Jasminum for the first time and compounds II, IV and VI were isolated from Jasminum officinale L. var. grandiflorum for the first time. PMID:18229614

Zhao, Gui-qin; Xia, Jing-jing; Dong, Jun-xing

2007-10-01

237

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

238

Cardiac Glycosides from Antiaris toxicaria with Potent Cardiotonic Activity  

PubMed Central

An ethanolic extract of Antiaris toxicaria trunk bark showed potent in vitro cardiotonic effect on isolated guinea pig atria. Bioassay-guided fractionation of the extract led to identification of 9 new cardiac glycosides (1–9, named antiarosides A-I), antiarotoxinin A (10), and 18 known compounds. Their structures were established using MS and NMR spectroscopic studies, including homonuclear and heteronuclear correlation experiments. The ability of these cardiotonic compounds to produce positive inotropic action and their safety indexes were examined in comparison with those of ouabain, a classical inhibitor of Na+/K+-ATPase. Malayoside (23) was nearly equipotent and had a similar safety index to ouabain in guinea pig atria. However, the maximal positive inotropic effect and safety index of 23 in papillary muscle were better than those of ouabain. An electrophysiological recording showed that 23 inhibited sodium pump current in a concentration-dependent manner. PMID:20553004

Shi, Li-Shian; Liao, Yu-Ren; Su, Ming-Jai; Lee, An-Sheng; Kuo, Ping-Chung; Damu, Amooru G.; Kuo, Sheng-Chu; Sun, Han-Dong; Lee, Kuo-Hsiung; Wu, Tian-Shung

2010-01-01

239

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

240

Flavonoid glycosides and pharmacological activity of Amphilophium paniculatum  

PubMed Central

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

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

2013-01-01

241

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

2014-01-01

242

Solubility enhancement of steviol glycosides and characterization of their inclusion complexes with gamma-cyclodextrin.  

PubMed

Steviol glycosidesrebaudioside (reb) A, C and D have low aqueous solubilities. To improve their aqueous solubilities, inclusion complex of steviol glycosides, reb A, C and D and gamma cyclodextrin were prepared by freeze drying method and further characterized by means of differential scanning calorimetry, Fourier transform infrared spectroscopy and Raman spectroscopy. The effect of gamma cyclodextrin on chemical shifts of the steviol glycosides was also studied in proton NMR experiments as well as in solid state (13)C CP/MAS NMR experiments. These results indicated that the steviol glycosides were clearly in inclusion complex formation with the gamma cyclodextrin which also results in solubility enhancement of these steviol glycosides. Phase solubility studies showed that amounts of soluble reb A, C and D increased with increasing amounts of gamma cyclodextrin indicating formation of 1:1 stoichiometric and higher order inclusion complexes. PMID:22174615

Upreti, Mani; Strassburger, Ken; Chen, You L; Wu, Shaoxiong; Prakash, Indra

2011-01-01

243

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

PubMed

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

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

2010-09-01

244

An unusual novel anti-oxidant dibenzoyl glycoside from Salvinia natans  

Microsoft Academic Search

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

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

2010-01-01

245

Ultra-sonication-assisted solvent extraction of quercetin glycosides from 'Idared' apple peels.  

PubMed

Quercetin and quercetin glycosides are physiologically active flavonol molecules that have been attributed numerous health benefits. Recovery of such molecules from plant matrices depends on a variety of factors including polarity of the extraction solvent. Among the solvents of a wide range of dielectric constants, methanol recovered the most quercetin and its glycosides from dehydrated 'Idared' apple peels. When ultra-sonication was employed to facilitate the extraction, exposure of 15 min of ultrasound wavelengths of dehydrated apple peel powder in 80% to 100% (v/v) methanol in 1:50 (w:v) solid to solvent ratio provided the optimum extraction conditions for quercetin and its glycosides. Acidification of extraction solvent with 0.1% (v/v) or higher concentrations of HCl led to hydrolysis of naturally occurring quercetin glycosides into the aglycone as an extraction artifact. PMID:22117169

Vasantha Rupasinghe, H P; Kathirvel, Priya; Huber, Gwendolyn M

2011-01-01

246

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

247

Cytotoxic holostane-type triterpene glycosides from the sea cucumber Pentacta quadrangularis.  

PubMed

Two new holostane-type triterpene glycosides, named pentactasides I (1) and II (2), and a new natural product, pentactaside III (3), together with two known glycosides, philinopsides A (4) and B (5), were isolated from the sea cucumber Pentacta quadrangularis. Their structures were elucidated by extensive spectroscopic analysis and chemical evidences. Compounds 1 and 2 possess the same trisaccharide moiety which is a rare structural feature among naturally occurring sea cucumber glycosides and has been infrequently reported, while 3 is a sulfated diglycoside. All the glycosides showed significant in vitro cytotoxicities against six tumor cell lines (P-388, A-549, MCF-7, MKN-28, HCT-116, and U87MG) with IC(50) in the range of 0.60-3.95 µM. PMID:20425691

Han, Hua; Xu, Qiang-Zhi; Tang, Hai-Feng; Yi, Yang-Hua; Gong, Wei

2010-11-01

248

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. PMID:23204424

Zheng, Fei

2013-01-01

249

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

250

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

PubMed

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

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

2014-10-01

251

Syntheses of acetylated steroid glycosides and selective cleavage of O-acetyl groups in sugar moiety  

Microsoft Academic Search

Acetylated 3?-O-?-glycosyl steroid derivatives were synthesized by the reaction of a new polyhydroxysteroid 3?,5?,6?-trihydroxypregn-16-en-20-one (2) with the peracetylated 1-bromo derivatives of d-glucose and d-galactose, respectively. Subsequent protection by excess acetic anhydride in pyridine selectively gave the 6?-O-acetylated steroid glycosides. Deprotection of the acetylated steroid glycosides separately with moderate catalysis dibutyltin oxide in methanol selectively removed all acetyl groups of sugar

Shao-Min Wang; Wen-Zhong Ge; Hong-Min Liu; Da-Peng Zou; Xue-Bin Yan

2004-01-01

252

Direct and correlated responses to selection on iridoid glycosides in Plantago lanceolata L  

Microsoft Academic Search

Plantago lanceolata L. (ribwort plantain) produces two costly terpenoid secondary plant compounds, the iridoid glycosides aucubin and catalpol. We performed an artificial selection experiment to investigate direct and correlated responses to selection on the constitutive level of iridoid glycosides in the leaves for four generations. Estimated realized heritabilities (+\\/-SE) were 0.23 +\\/- 0.07 and 0.23 +\\/- 0.04 for upward and

H. B. Marak; A. Biere; J. M. M. Van Damme

2000-01-01

253

[Radionuclide study of the influence of beta-adrenoblockaders on the cardiotonic effect of cardiac glycosides].  

PubMed

Radiocardiography was used in 234 patients to explore the effect of corglycon, a glycoside drug obtained from Convallaria L., cardiac glycoside (CG) digoxin, beta-adrenoblockers (BAB) anapriline and trasicor, and combinations of CG and BAB on the minute and stroke volumes of the circulation and heart rate. It has been shown that administration of CG coupled with BAB increasing the tolerance to the cardiotoxic effect of CG does not entail a reduction of their beneficial inotropic action. PMID:6133778

Gendenshte?n, E I; Vladimirov, Iu P; Koledinov, V I; Za?tsev, V M

1983-01-01

254

Iridoid glycoside sequestration by Thessalia leanira (Lepidoptera: Nymphalidae) feeding on Castilleja integra (Scrophulariaceae)  

Microsoft Academic Search

A small population of a polyvoltine checkerspot butterfly,Thessalia leanira fulvia (also known asChlosyne leanira ssp.fulvia), was found to useCastilleja integra as a larval food plant at a localized site (Burnt Mill) southwest of Pueblo, Colorado. Field-captured adult butterflies contained the major iridoid glycosides (catalpol and macfadienoside) of theCastilleja. The content of a third iridoid glycoside, methyl shanzhiside, was also relatively

Elliott W. Mead; Tommaso A. Foderaro; Dale R. Gardner; Frank R. Stermitz

1993-01-01

255

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

SciTech Connect

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

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

1980-08-01

256

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

PubMed

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

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

2014-11-19

257

Effect of chito-oligosaccharide on the intestinal absorptions of phenylethanoid glycosides in Fructus Forsythiae extract.  

PubMed

Phenylethanoid glycosides, the main active ingredients in Fructus Forsythiae extract possesses strong antibacterial, antioxidant and antiviral effects, and their contents were higher largely than that of other ingredients such as lignans and flavones, but their absolute bioavailability orally was significantly low, which influenced clinical efficacies of its oral preparations seriously. In the present study, the absorption mechanism of phenylethanoid glycosides was studied using in vitro Caco-2 cell model. And the effect of chito-oligosaccharide (COS) on the intestinal absorption of phenylethanoid glycosides in Fructus Forsythiae extract was investigated using in vitro, in situ and in vivo models. The pharmacological effects such as antiviral activity improvement by COS were verified by MDCK cell damage inhibition rate after influenza virus propagation. The observations from in vitro Caco-2 cell showed that the absorption of phenylethanoid glycosides in Fructus Forsythiae extract so with that in monomers was mainly restricted by the tight junctions, and influenced by efflux transporters (P-gp and MRP2). Meanwhile, the absorption of phenylethanoid glycosides in Fructus Forsythiae extract could be improved by COS. Besides, COS at the same low, medium and high concentrations caused a significant, concentration-dependent increase in the Papp-value for phenylethanoid glycosides compared to the control group (p<0.05), and was all safe for the Caco-2 cells. The observations from single-pass intestinal perfusion in situ model showed that the intestinal absorption of phenylethanoid glycosides can be enhanced by COS. Meanwhile, the absorption enhancing effect of phenylethanoid glycosides might be saturable in different intestine sites. In pharmacokinetics study, COS at dosage of 25mg/kg improved the bioavailability of phenylethanoid glycosides in Fructus Forsythiae extract to the greatest extent, and was safe for gastrointestine from morphological observation. In addition, treatment with Fructus Forsythiae extract with COS at dosage of 25mg/kg prevented MDCK cell damage upon influenza virus propagation better than that of control. All findings above suggested that COS at dosage of 25mg/kg might be safe and effective absorption enhancer for improving the bioavailability of phenylethanoid glycosides and the antiviral activity in vitro in Fructus Forsythiae extract. PMID:25442264

Zhou, Wei; Tan, Xiaobin; Shan, Jinjun; Liu, Ting; Cai, Baochang; Di, Liuqing

2014-10-15

258

Synthesis of betavulgaroside III, a representative triterpene seco-glycoside.  

PubMed

Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold. PMID:18529027

Zhu, Shilei; Li, Yingxia; Yu, Biao

2008-07-01

259

Thermus thermophilus Glycoside Hydrolase Family 57 Branching Enzyme  

PubMed Central

Branching enzyme (EC 2.4.1.18; glycogen branching enzyme; GBE) catalyzes the formation of ?1,6-branching points in glycogen. Until recently it was believed that all GBEs belong to glycoside hydrolase family 13 (GH13). Here we describe the cloning and expression of the Thermus thermophilus family GH57-type GBE and report its biochemical properties and crystal structure at 1.35-? resolution. The enzyme has a central (?/?)7-fold catalytic domain A with an inserted domain B between ?2 and ?5 and an ?-helix-rich C-terminal domain, which is shown to be essential for substrate binding and catalysis. A maltotriose was modeled in the active site of the enzyme which suggests that there is insufficient space for simultaneously binding of donor and acceptor substrates, and that the donor substrate must be cleaved before acceptor substrate can bind. The biochemical assessment showed that the GH57 GBE possesses about 4% hydrolytic activity with amylose and in vitro forms a glucan product with a novel fine structure, demonstrating that the GH57 GBE is clearly different from the GH13 GBEs characterized to date. PMID:21097495

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

2011-01-01

260

New steroidal glycosides from Hosta plantaginea (Lam.) Aschers.  

PubMed

Four new furostanol glycosides were isolated from the flowers of Hosta plantaginea (Lam.) Aschers. On the basis of spectroscopic methods including 1D and 2D NMR experiments, their structures were elucidated as 26-O-?-d-glucopyranosyl-(25R)-22-O-methyl-5?-furostan-2?,3?,22?,26-tetrol 3-O-?-l-rhamnopyranosyl-(1 ? 4)-O-?-d-xylopyranosyl-(1 ? 3)-[O-?-d-glucopyranosyl-(1 ? 2)]-O-?-d-glucopyranosyl-(1 ? 4)-?-d-galactopyranoside (hostaplantagineoside A, 1), 26-O-?-d-glucopyranosyl-(25R)-5?-furostan-20(22)-ene-2?,3?,26-triol-3-O-?-d-glucopyranosyl-(1 ? 2)-[O-?-d-xylopyranosyl-(1 ? 3)]-O-?-d-glucopyranosyl-(1 ? 4)-?-d-galactopyranoside (hostaplantagineoside B, 2), 26-O-?-d-glucopyranosyl-(25R)-5?-furostan-22(23)-ene-2?,3?,20?,26-tetraol-3-O-?-d-glucopyranosyl-(1 ? 2)-[O-?-d-xylopyranosyl-(1 ? 3)]-O-?-d-glucopyranosyl-(1 ? 4)-O-?-d-galactopyranoside (hostaplantagineoside C, 3), 26-O-?-d-glucopyranosyl-(25R)-5?-furostan-20(22)-ene-2?,3?,26-triol-3-O-?-l-rhamnopyranosyl-(1 ? 4)-O-?-d-xylopyranosyl-(1 ? 3)-[O-?-d-glucopyranosyl-(1 ? 2)]-O-?-d-glucopyranosyl-(1 ? 4)-?-d-galactopyranoside (hostaplantagineoside D, 4). PMID:25559690

Li, Xiao-Juan; Wang, Li; Xue, Pei-Feng; Xie, Hong-Xia; Wei, Hui; Wang, Jing

2015-03-01

261

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

262

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

PubMed

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

Förster, Nadja; Ulrichs, Christian; Zander, Matthias; Kätzel, Ralf; Mewis, Inga

2010-07-28

263

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

264

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

PubMed Central

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

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

2009-01-01

265

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

266

Bioprospecting metagenomics of decaying wood: mining for new glycoside hydrolases  

PubMed Central

Background To efficiently deconstruct recalcitrant plant biomass to fermentable sugars in industrial processes, biocatalysts of higher performance and lower cost are required. The genetic diversity found in the metagenomes of natural microbial biomass decay communities may harbor such enzymes. Our goal was to discover and characterize new glycoside hydrolases (GHases) from microbial biomass decay communities, especially those from unknown or never previously cultivated microorganisms. Results From the metagenome sequences of an anaerobic microbial community actively decaying poplar biomass, we identified approximately 4,000 GHase homologs. Based on homology to GHase families/activities of interest and the quality of the sequences, candidates were selected for full-length cloning and subsequent expression. As an alternative strategy, a metagenome expression library was constructed and screened for GHase activities. These combined efforts resulted in the cloning of four novel GHases that could be successfully expressed in Escherichia coli. Further characterization showed that two enzymes showed significant activity on p-nitrophenyl-?-L-arabinofuranoside, one enzyme had significant activity against p-nitrophenyl-?-D-glucopyranoside, and one enzyme showed significant activity against p-nitrophenyl-?-D-xylopyranoside. Enzymes were also tested in the presence of ionic liquids. Conclusions Metagenomics provides a good resource for mining novel biomass degrading enzymes and for screening of cellulolytic enzyme activities. The four GHases that were cloned may have potential application for deconstruction of biomass pretreated with ionic liquids, as they remain active in the presence of up to 20% ionic liquid (except for 1-ethyl-3-methylimidazolium diethyl phosphate). Alternatively, ionic liquids might be used to immobilize or stabilize these enzymes for minimal solvent processing of biomass. PMID:21816041

2011-01-01

267

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. PMID:5419749

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

1970-01-01

268

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

PubMed Central

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

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

2014-01-01

269

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

PubMed

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

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

2014-01-01

270

High-performance liquid chromatographic determination of secondary cardiac glycosides in Digitalis purpurea leaves.  

PubMed

An analytical method for the determination of secondary cardiac glycosides in Digitalis purpurea leaves by high-performance liquid chromatography (HPLC) is described. The procedure consisted of extraction of dry leaf powder with ethanol-chloroform (2:1) and clean-up by Sep-Pak cartridges prior to HPLC analysis. HPLC was performed on an octylsilyl bonded silica column, using acetonitrile-methanol-water (4:4:5) for trisdigitoxosides and acetonitrile-methanol-water (8:30:43) for strospeside; the effluent was monitored by ultraviolet detection (at 220 nm). Quantitation of these cardiac glycosides was carried out by the internal standard method. The amounts of digitoxin, gitoxin, gitaloxin and strospeside per 100 mg of dry leaf powder were estimated to be 22.6, 14.0, 54.7 and 1.9 micrograms, respectively. The method is sufficiently sensitive and reproducible to assay secondary glycosides in Digitalis purpurea leaves. PMID:2808604

Fujii, Y; Ikeda, Y; Yamazaki, M

1989-10-01

271

Resin glycosides from the roots of Ipomoea tyrianthina and their biological activity.  

PubMed

Seven new tetrasaccharide glycosides, tyrianthins 1-7 (1-7), along with six known glycolipids were isolated from the roots of Ipomoea tyrianthina, and their structures were elucidated by spectroscopic and chemical methods. The content of resin glycosides in samples collected in three different regions was analyzed and compared, and the results showed that the flowering or dry season did not have any effect on the chemical composition for the same locality, but the growing location itself did affect the chemical composition of resin glycosides. Intraperitoneal administration to mice of tyrianthin 6 (6) resulted in antidepressant activity. Tyrianthin 6 (6), scammonin 1 (8), and scammonin 2 (9) exhibited dose-dependent protective effects against pentylenetetrazole-induced seizures. Also, tyrianthin 6 (6) and scammonin 2 (9) produced relaxant effects on spontaneous contractions in the isolated rat ileum. PMID:17309299

Mirón-López, Gumersindo; Herrera-Ruiz, Maribel; Estrada-Soto, Samuel; Aguirre-Crespo, Francisco; Vazquez-Navarrete, Lorena; León-Rivera, Ismael

2007-04-01

272

(10, k) Reversible Multiples  

E-print Network

We consider the integers having the property of reversing when multiplied by a specific integer k. First, we proved that k should be either 1, 4 or 9. Second, we classify these integers as (10, 1)- reverse multiples, (10, 4)- reverse multiples and (10, 9)- reverse multiples. Then we conclude their general form.

Madline Al- Tahan

2015-04-20

273

Leaf variation in iridoid glycoside content of Plantago lanceolata (Plantaginaceae) and oviposition of the buckeye, Junonia coenia (Nymphalidae)  

Microsoft Academic Search

Summary Chemical analysis of each individual leaf of fivePlantago lanceolata (Plantaginaceae) plants showed that iridoid glycoside content increased from undetectable in the oldest photosynthetic leaves to over 9% dry weight in the youngest leaves. The relative proportion of the two iridoid glycosides inP. lanceolata also changed with leaf age: older leaves had significantly more aucubin, whereas the youngest leaves had

Gretchen K. Klockars; M. Deane Bowers; Barbara Cooney

1993-01-01

274

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

PubMed

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

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

2013-11-01

275

Beneficial effects of tripterygium glycosides tablet on biomarkers in patients with ankylosing spondylitis.  

PubMed

The aim of the current study was to explore the effects and possible mechanisms of tripterygium glycosides tablet (TGT) in the treatment of active ankylosing spondylitis (AS). Thirty?six patients with active AS were given a 20 mg TGT treatment three times per day for 12 weeks, and 21 unrelated healthy controls were recruited as the control group. Efficacy measures included the Bath AS disease activity index (BASDAI), erythrocyte sedimentation rate (ESR) and C?reactive protein (CRP) prior and subsequent to TGT treatment. Serum dickkopf homolog 1 (DKK1) and interleukin-17 (IL?17) levels before and after TGT treatment were assessed using reverse transcription?quantitative polymerase chain reaction (RT?qPCR) and ELISA assay. The levels of several serum biomarkers were determined by ELISA, including receptor activator of nuclear factor ??B ligand (RANKL), osteoprotegerin (OPG), bone alkaline phosphatase (BAP), bone morphogenetic protein?2 (BMP?2), matrix metalloproteinase?3 (MMP?3), cross?linked telopeptide of type II collagen (CTX?II), vascular endothelial growth factor (VEGF), and prostaglandin E2 (PGE2). After 12 weeks of TGT treatment, the BASDAI score of the patients was significantly reduced (P<0.05), their levels of ESR and CRP were significantly reduced to a normal level (P<0.05, P<0.05), RT?PCR and ELISA showed a significant increase in the level of DKK1 expression (P<0.05) and a significant decreased IL?17 expression (P<0.05), there was a significant increase in the expression of OPG, BAP and BMP?2 (P<0.01, P<0.01, P<0.01) and a significant reduction in the expression levels of RANKL, CTX?II. MMP?3, PGE2, and VEGF (P<0.01, P<0.01, P<0.01, P<0.05, P<0.01) compared with those of the controls. TGT is effective at improving the signs and symptoms of patients with AS through the regulation of serum biomarkers, and the mechanisms may be associated with the anti?inflammatory effect, inhibition of new bone formation and potential bone?protective effects. PMID:25760304

Ji, Wei; Chen, Yajun; Zhao, Xia; Guo, Yunke; Zhong, Lingyu; Li, Honggang; Wang, Dan; Song, Yanna

2015-07-01

276

The rate of spontaneous cleavage of the glycosidic bond of adenosine  

PubMed Central

Previous estimates of the rate of spontaneous cleavage of the glycosidic bond of adenosine were determined by extrapolating the rates of the acid - and base-catalyzed reactions to neutral pH. Here we show that cleavage also proceeds through a pH-independent mechanism. Rate constants were determined as a function of temperature at pH 7 and a linear Arrhenius plot was constructed. Uncatalyzed cleavage occurs with a rate constant of 3.7 × 10?12 s?1 at 25 °C, and the rate enhancement generated by the corresponding glycoside hydrolase is ~5 × 1012-fold. PMID:20580404

Stockbridge, Randy B.; Schroeder, Gottfried K.; Wolfenden, Richard

2010-01-01

277

Oviposition stimulants for the monarch butterfly: Flavonol glycosides from Asclepias curassavica  

Microsoft Academic Search

The monarch butterfly Danaus plexippus oviposits on milkweed plants, primarily within the Asclepiadaceae. Oviposition stimulants responsible for host plant recognition were isolated from Asclepias curassavica. Six flavonoid glycosides-quercetin 3-O-(2?,6?-?-l-dirhamnopyranosyl)-?-d-galactopyranoside, quercetin 3-O-?-d-glucopyranosyl-(1 ? 6)-?-d-galactopyranoside, quercetin 3-O-(2?-O-?-l-rhamnopyranosyl)-?-d-galactopyranoside, quercetin 3-O-?-l-rhamnopyranosyl-(1 ? 6-?-d-glucopyranoside, quercetin 3-O-?-d-galactopyranoside, quercetin 3-O-?-d-glucopyranoside, and an unidentified flavonoid mixture were isolated and characterized from this plant. An additional glycoside, possibly quercetin

Meena Haribal; J. Alan A. Renwick

1996-01-01

278

C(22)-steroidal lactone glycosides from stems and leaves of Paris polyphylla var. yunnanensis.  

PubMed

Further phytochemical investigation on the stems and leaves of Paris polyphylla var. yunnanensis has led to the isolation of three C(22)-steroidal lactone glycosides. Two of these are new compounds, designated as chonglouoside SL-7 (1) and chonglouoside SL-8 (2). Their structures were elucidated on the basis of extensive spectroscopic analysis, as well as comparison with the reported spectroscopic data. This is the first report of C(22)-steroidal lactone glycosides isolated from the Paris genus. Compounds 1 and 3 showed moderate antimicrobic activity against Propionibacterium acnes with MIC values of 31.3 and 3.9?g/mL, respectively. PMID:23262268

Qin, Xu-Jie; Chen, Chang-Xiang; Ni, Wei; Yan, Huan; Liu, Hai-Yang

2013-01-01

279

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

PubMed

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

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

2011-01-01

280

Flavonoid glycoside variations in the progeny of wild specimens of Centaurea montana and comments on the origin of their natural diversity  

Microsoft Academic Search

From a series of wild accessions of Centaurea montana displaying markedly dissimilar flavonoid phenotypes (notably C-glycosides vs. O-glycosides) different experimental breeding operations were performed. Variation was observed in individual glycosidic profiles of progeny, the importance of which depended on the parental phenotypes and the genetic proximity of the partners employed (combinations of wild specimens, inbred, plants or backcrosses operations). Most

Jean-François Gonnet

1996-01-01

281

Flavonoid glycosides of spore-bearing stems of Equisetum arvense  

Microsoft Academic Search

In an extract of spore-bearing stems ofEquisetum arvense L. (field horsetail) saponaretin, apigenin 5-glucoside, luteolin 5-glucoside, kaempferol 3-sophoroside, quercetin 3-glucoside, 4-hydroxy-6-(2-hydroxyethyl)-2,2,5,7-tetramethylindanone, and a compound of ketonic nature, isolated previously from an extract of the herbage of the field horsetail, have been identified by high-performance liquid chromatography. The characteristics of the chromatographic behavior of glycosylated flavones under the conditions of reversed-phase

A. I. Syrchina; V. G. Gorokhova; N. A. Tyukavkina; V. A. Babkin; M. G. Voronkov

1980-01-01

282

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

283

SnCl(4)- and TiCl(4)-catalyzed anomerization of acylated O- and S-glycosides: analysis of factors that lead to higher ?:? anomer ratios and reaction rates.  

PubMed

The quantification of factors that influence both rates and stereoselectivity of anomerization reactions catalyzed by SnCl(4) and TiCl(4) and how this has informed the synthesis of ?-O- and ?-S-glycolipids is discussed. The SnCl(4)-catalyzed anomerization reactions of ?-S- and ?-O-glycosides of 18 substrates followed first order equilibrium kinetics and k(f) + k(r) values were obtained, where k(f) is the rate constant for the forward reaction (? ? ?) and k(r) is the rate constant for the reverse reaction (? ? ?). Comparison of the k(f) + k(r) values showed that reactions of glucuronic acid or galacturonic acid derivatives were ?10 to 3000 times faster than those of related glucoside and galactopyranoside counterparts and ?:? ratios were generally also higher. Stereoelectronic effects contributed from galacto-configured compounds were up to 2-fold faster than those of corresponding glucosides. The introduction of groups, including protecting groups, which are increasingly electron releasing generally led to rate enhancements. The anomerization of S-glycosides was consistently faster than that of corresponding O-glycosides. Reactions were generally faster for reactions with TiCl(4) than those with SnCl(4). Anomeric ratios depended on the Lewis acid, the number equivalents of the Lewis acid, temperature, and substrate. Very high ratios of ?-products for both O- and S-glucuronides were observed for reactions promoted by TiCl(4); for these substrates TiCl(4) was superior to SnCl(4). Anomeric ratios from anomerization of S-glucosides were higher with SnCl(4) than with TiCl(4). The dependence of equilibrium ratio on Lewis acid and the number of equivalents of Lewis acid indicated that the equilibrium ratio is determined by a complex of the saccharide residue bound to the Lewis acid and not the free glycoside. The high ?:? ratios observed for anomerization of both O- and S-glycuronic acids can be explained by coordination of the C-1 heteroatom and C-6 carbonyl group of the product to the Lewis acid, which would enhance the anomeric effect by increasing the electron-withdrawing ability of the anomeric substituent and lead to an increase in the proportion of the ?-anomer. Such an observation would argue against the existence of a reverse anomeric effect. Support for a chelation-induced endocyclic cleavage mechanism for the anomerization is provided by the trapping of a key intermediate. The data herein will help predict the tendency of ?-glycosides to undergo anomerization; this includes cases where 1,2-trans glycosides are initial products of glycosidation reactions catalyzed by TiCl(4) or SnCl(4). PMID:20836488

Pilgrim, Wayne; Murphy, Paul V

2010-10-15

284

HIV-1 Reverse Transcription  

PubMed Central

Reverse transcription and integration are the defining features of the Retroviridae; the common name “retrovirus” derives from the fact that these viruses use a virally encoded enzyme, reverse transcriptase (RT), to convert their RNA genomes into DNA. Reverse transcription is an essential step in retroviral replication. This article presents an overview of reverse transcription, briefly describes the structure and function of RT, provides an introduction to some of the cellular and viral factors that can affect reverse transcription, and discusses fidelity and recombination, two processes in which reverse transcription plays an important role. In keeping with the theme of the collection, the emphasis is on HIV-1 and HIV-1 RT. PMID:23028129

Hu, Wei-Shau; Hughes, Stephen H.

2012-01-01

285

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

PubMed

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

Talisman, Ian J; Kumar, Vineet; Deschamps, Jeffrey R; Frisch, Mark; Malhotra, Sanjay V

2011-11-01

286

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

PubMed Central

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

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

2011-01-01

287

Disposition and metabolism of the antitumor glycoside phyllanthoside in mouse and beagle dog  

Microsoft Academic Search

Phyllanthoside is a naturally occurring glycoside with activity against IP transplantable murine tumors. Phyllanthoside administered IV, to mice at a nontoxic dose of 16 mg\\/kg could not be detected in blood or plasma even 30 s after administration. There was rapid formation of a less polar metabolite, which disappeared with a half-life of about 10 min. When phyllanthoside was administered

David J. Moore; Garth Powis

1986-01-01

288

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

289

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. PMID:17676918

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

2008-01-01

290

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. PMID:24900406

2012-01-01

291

High pressure: a tool to improve the enzymatic production of glycosides  

Microsoft Academic Search

Naringinase, an enzyme complex that expresses ? -l-rhamnosidase and ? -d-glucosidase activities in native state, can be used to deglycosylate natural glycosides. The selective inactivation of one of these activities will allow the biosynthesis of different bioactive compounds in a simple, effective and cheap way. In this work, pressure and temperature were the tools used to selectively inactivate the activities

Helder Vila-Real; António J. Alfaia; António R. Calado; Robert S. Phillips; Maria H. L. Ribeiro

2011-01-01

292

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

293

New oleanan-type triterpene and cincholic acid glycosides from Peruvian "Uña 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

294

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

295

Targeted Discovery of Glycoside Hydrolases from a Switchgrass-Adapted Compost Community  

E-print Network

Targeted Discovery of Glycoside Hydrolases from a Switchgrass-Adapted Compost Community Martin avenue of research in this area. Here we added a green-waste compost inoculum to switchgrass (Panicum virgatum) and simulated thermophilic composting in a bioreactor to select for a switchgrass

Hazen, Terry

296

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

297

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

298

Probing Electrostatic Interactions along the Reaction Pathway of a Glycoside Hydrolase: Histidine Characterization by NMR Spectroscopy  

E-print Network

Probing Electrostatic Interactions along the Reaction Pathway of a Glycoside Hydrolase: Histidine- ticular, understanding these interactions and their changes along the reaction pathway of an enzyme as a hydrogen bond donor and acceptor but also as the positively charged component of a salt bridge. As such

McIntosh, Lawrence P.

299

Structural complexes in the squid giant axon membrane sensitive to ionic concentrations and cardiac glycosides  

Microsoft Academic Search

Giant nerve fibers of squid Sepioteuthis sepioidea were incubated for 10 min in artificial sea water (ASW) under control conditions, in the absence of various ions, and in the presence of cardiac glycosides. The nerve fibers were fixed in OsO, and embedded in Epon, and structural complexes along the axolemma were studied. These complexes consist of a portion of axolemma

GLORIA M. VILLEGAS; JORGE VILLEGAS

1976-01-01

300

Differential El Ion Fragmentation Pathways for Peracetylated C-Glycoside Ketals  

Technology Transfer Automated Retrieval System (TEKTRAN)

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

301

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

302

Patterns of Iridoid Glycoside Production and Induction in Plantago lanceolata and the Importance of Plant Age  

Microsoft Academic Search

Induction of allelochemicals is one way that plants efficiently deploy defenses against herbivory. In two separate experiments we investigated the time course of this inductive response and the importance of the timing of herbivory for Plantago lanceolata (Plantaginaceae). We found a localized induced response of catalpol and the ratio of catalpol to total iridoid glycosides in damaged leaves that was

Alexander Fuchs; M. Deane Bowers

2004-01-01

303

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

304

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

305

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

306

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. PMID:22544243

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

307

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

PubMed

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

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

2015-01-01

308

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

309

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

310

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

PubMed

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

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

2012-11-01

311

Triterpene glycosides from the sea cucumber Cladolabes schmeltzii. II. Structure and biological action of cladolosides A1-A6 .  

PubMed

Six new triterpene glycosides, cladolosides Al-A6 (1-6), have been isolated from the Vietnamese sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. All the glycosides have nonsulfated tetrasaccharide linear carbohydrate moieties. Glycoside 6 has a glucose residue as the third monosaccharide unit, while the rest of the compounds comprise a xylose in this postion of the carbohydrate chain. Glycosides 1-6 differ from each other in the structures of their holostane aglycones. Cytotoxic activities of glycosides 1-6 were studied against mouse spleenocytes, along with hemolytic activities against mouse erythrocytes. All the compounds, except cladoloside A5 (5) posessing a hydroxy-group in the aglycone side chain, demonstrated rather strong cytotoxic and hemolytic effects. The most active glycosides were cladolosides A1 (1) and A2 (2) having two O-acetic groups and the xylose residue in the third position of the sugar chain. PMID:25522529

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

2014-10-01

312

Influence of iridoid glycoside containing host plants on midgut ?-glucosidase activity in a polyphagous caterpillar, Spilosoma virginica Fabricius (Arctiidae).  

PubMed

Iridoid glycosides are secondary plant compounds that have deterrent, growth reducing or even toxic effects on non-adapted herbivorous insects. To investigate the effects of iridoid glycoside containing plants on the digestive metabolism of a generalist herbivore, larvae of Spilosoma virginica (Lepidoptera: Arctiidae) were reared on three plant species that differ in their secondary plant chemistry: Taraxacum officinale (no iridoid glycosides), Plantago major (low iridoid glycoside content), and P. lanceolata (high iridoid glycoside content). Midguts of fifth instar larvae were assayed for the activity and kinetic properties of ?-glucosidase using different substrates. Compared to the larvae on T. officinale, the ?-glucosidase activity of larvae feeding on P. lanceolata was significantly lower measured with 4-nitrophenyl-?-d-glucopyranoside. Using the iridoid glycoside aucubin as a substrate, we did not find differences in the ?-glucosidase activity of the larvae reared on the three plants. Heat inactivation experiments revealed the existence of a heat-labile and a more heat-stable ?-glucosidase with similar Michaelis constants for 4-nitrophenyl-?-d-glucopyranoside. We discuss possible mechanisms leading to the observed decrease of ?-glucosidase activity for larvae reared on P. lanceolata and its relevance for generalist herbivores in adapting to iridoid glycoside containing plant species and their use as potential host plants. PMID:20727899

Pankoke, Helga; Bowers, M Deane; Dobler, Susanne

2010-12-01

313

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

PubMed

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

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

2015-04-01

314

On the sarcolemmal site of action of cardiac glycosides.  

PubMed

An electron microscopic study of the guinea pig myocardial cell was conducted. By the use of LaC13, two morphologically distinct tubular systems could be demonstrated. The larger one represents the transverse tubular system which originates from the plasma membrane and is continous with the extracellular space (ECS). In the heart muscle cell it forms a three-dimensional network and it closely apposed to the myofilaments at the level of the Z and I bands. A comparatively small and sparsely developed tubular system which is not accessible from the ECS represents the sarcoplasmic reticulum (SR). By means of sucrose-density centrifugation in a discontinuous gradient two main microsomal fractions were obtained (F1 and F3). The pre-existing structure of F1 could be identified as the transverse tubular system, whereas F3 originates from the SR. The morphological features (e. g., an enclosed basement membrane) and the fact that after perfusion of hearts with [3H] inulin and preparation of microsomes the ECS marker is almost completely retained in F1 indicate that upon fractionation and vesiculation inside-out vesicles are formed which trap the former extracellular fluid. Moreover, the former extracellular surface is hidden and no longer accessible for membrane-impermeable compounds. After perfusion of hearts with [3H] ouabain and fractionation and centrifugation the radioactive material was found to accumulate in F1, the kinetics being identical with that of binding to the intact tissue and with the time course of the inotropic action of ouabain. The inside-out vesicles derived from the plasma membrane are characterized by the presence of a (Na+-K+)-ATPase activity, an outward Ca pump, a high binding capacity for Ca, and a low Ca pereability. Since the (Na+-K+)-ATPase is known to react with cardiac glycosides (CG) at the outer cell surface it was not surprising to find a complete lack of inhibition of the enzyme by the membrane-impermeable CG ouabain if administered to the intact sarcolemmal microsome. After disruption of the microsomes, however, a considerable inhibition of the (Na+-K+)-ATPase became demonstrable. Similarly, the Ca permeability of the plasma membranes could only be enhanced by CG if interacting with the former outside. Although ouabain again failed to exert any action, the membrane permeable digoxin increased the Ca pereability of the intact vesicular membrane. The rate of Ca transport as an indicator of the Ca pump activity remained unaffected by CG provided from either side of the membrane. The passive Ca binding to the plasma membrane, which results in a concentration up to 5 mM in this structure, is thought to represent the Ca pool essential for excitation-contraction coupling. The CG are thought to alter the Ca binding in this pool, thus rendering depolarization more effective in releasing Ca++. PMID:130660

Lüllmann, H; Peters, T

1976-01-01

315

Reversion of flowering  

Microsoft Academic Search

Reversion from floral to vegetative growth is under environmental control in many plant species. However the factors regulating\\u000a floral reversion, and the events at the shoot apex that take place when it occurs, have received less attention than those\\u000a associated with the transition to flowering.\\u000a \\u000a Reversions may be categorized as flower reversion, in which the flower meristem resumes leaf production,

N. H. Battey; R. F. Lyndon

1990-01-01

316

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

317

Sinularosides A and B, bioactive 9,11-secosteroidal glycosides from the South China Sea soft coral Sinularia humilis Ofwegen.  

PubMed

Two new 9,11-secosteroidal glycosides, namely, sinularosides A and B (1, 2), together with the known pregnene glycoside 3?-(?-xylopyranosyloxy)-5?-pregna-20-ene (3), were isolated from the South China Sea soft coral Sinularia humilis Ofwegen. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. This is the first report of 9,11-secosteroidal glycosides from a soft coral and from nature. In in vitro bioassays, the new compounds exhibited potent antimicrobial activities and showed no growth inhibition activity against the tumor cells HepG2 and Caco-2. PMID:22946634

Sun, Peng; Meng, Li-Yuan; Tang, Hua; Liu, Bao-Shu; Li, Ling; Yi, Yanghua; Zhang, Wen

2012-09-28

318

Reversal of Oral Anticoagulation  

PubMed Central

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

Limdi, Nita A.

2013-01-01

319

High-performance liquid chromatographic method for the analysis of anthraquinone glycosides and aglycones in madder root ( Rubia tinctorum L.)  

Microsoft Academic Search

A HPLC method has been developed for the simultaneous characterisation of anthraquinone glycosides and aglycones in extracts of Rubia tinctorum L. The anthraquinones are separated on an end-capped C18-RP column with a water–acetonitrile gradient as eluent and measured with UV detection at 250 nm. With this method the glycosides lucidin primeveroside and ruberythric acid and the aglycones lucidin, alizarin, purpurin,

Goverdina C. H. Derksen; Teris A. van Beek; Æde de Groot; Anthony Capelle

1998-01-01

320

Structures, kinetics, and modeling of glycoside hydrolase family 44 endoglucanases from Clostridium acetobutylicum and Ruminococcus flavefaciens FD1  

Microsoft Academic Search

Glycoside hydrolases (GH) are enzymes that hydrolyze glycosidic bonds between carbohydrates. Family 44 contains endo- and xylo- glucanases capable of hydrolyzing cellulose and hemicelluose. Two members produced by Clostridium acetobutylicum and Ruminococcus flavefaciens FD-1 are the subjects of characterization work in this dissertation.\\u000aThe EG from Clostridium acetobutylicum was characterized both structurally and kinetically. Crystallization and x-ray diffraction to 2.2-y

Christopher Donald Warner

2010-01-01

321

Identification of the Catalytic Residues in Family 52 Glycoside Hydrolase, a  Xylosidase from Geobacillus stearothermophilus T-6  

Microsoft Academic Search

-D-Xylosidases (EC 3.2.1.37) are exo-type glycoside hy- drolases that hydrolyze short xylooligosaccharides to xylose units. The enzymatic hydrolysis of the glycosidic bond involves two carboxylic acid residues, and their identification, together with the stereochemistry of the reaction, provides crucial information on the catalytic mechanism. Two catalytic mutants of a -xylosidase from Geobacillus stearothermophilus T-6 were subjected to detailed kinetic analysis

Tsafrir Bravman; Valery Belakhov; Dmitry Solomon; Gil Shoham; Bernard Henrissat; Timor Baasov; Yuval Shoham

2003-01-01

322

Secondary chemistry of hybrid and parental willows: Phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala , and their hybrids  

Microsoft Academic Search

Salix sericea andS. eriocephala differ markedly in secondary chemistry.S. sericea produces phenolic glycosides, salicortin and 2?-cinnamoylsalicortin, and low concentrations of condensed tannin. In contrast,S. eriocephala produces no phenolic glycosides, but high concentrations of condensed tannins. Hybrid chemistry is intermediate for both types of chemicals, suggesting predominantly additive inheritance of these two defensive chemical systems from the parental species. However, there

Colin M. Orians; Robert S. Fritz

1995-01-01

323

O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids.  

PubMed

We herein report O-glycosidation reactions promoted via silver N-heterocyclic carbene complexes formed in situ in ionic liquids. Seven different room temperature ionic liquids were screened for the glycosidation reaction of 4-nitrophenol with tetra-O-acetyl-?-d-galactopyranosyl bromide. Good to excellent yields were obtained using Ag-NHC complexes derived from imidazolium halide salts to promote the glycosidation reaction, whereas yields considered moderate to low were obtained without use of the silver carbene complex. Anion metathesis of the ionic liquids with inexpensive alkylammonium halides also resulted in silver N-heterocyclic carbene formation and subsequent O-glycosidation in the presence of silver carbonate. Effective utility of this methodology has been demonstrated with biologically relevant acceptors (including flavones and steroids) where O-?-glycoside products were obtained selectively in moderate to good yields. We have also demonstrated that the Ag-NHC complex is a superior promoter to traditionally used silver carbonate for the glycosidation of polyphenolic acceptors. The ionic liquids used in the study could be recycled three times without apparent loss in activity. PMID:21459367

Talisman, Ian Jamie; Kumar, Vineet; Razzaghy, Jacqueline; Malhotra, Sanjay V

2011-05-15

324

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

PubMed

(OFI) contains health-promoting compounds like flavonoids, being the isorhamnetin glycosides the most abundant. We evaluated the effect of OFI extracts with different isorhamnetin glycosides against two different human colon cancer cells (HT-29 and Caco2). The extracts were obtained by alkaline hydrolysis with NaOH at 40 °C during 15, 30 or 60 min. Tri and diglycosides were the most abundant isorhamnetin glycosides, therefore these compounds were isolated to compare their cytotoxic effect with the obtained from the extracts. The OFI extracts and purified isorhamnetin glycosides were more cytotoxic against HT-29 cells than Caco2 cells. OFI-30 exhibited the lowest IC50 value against HT-29 (4.9?±?0.5 ?g/mL) and against Caco2 (8.2?±?0.3 ?g/mL). Isorhamnetin diglycosides IG5 and IG6 were more cytotoxic than pure isorhamnetin aglycone or triglycosides when they were tested in HT-29 cells. Bioluminescent analysis revealed increased activity of caspase 3/7 in OFI extracts-treated cells, particularly for the extract with the highest concentration of isorhamnetin triglycosides. Flow cytometry analysis confirmed that OFI extract and isorhamnetin glycosides induced a higher percentage of apoptosis in HT-29 than in Caco2, while isorhamnetin was more apoptotic in Caco2. This research demonstrated that glycosilation affected antiproliferative effect of pure isorhamnetin glycosides or when they are mixed with other phytochemicals in an extract obtained from OFI. PMID:25186940

Antunes-Ricardo, Marilena; Moreno-García, Beatriz E; Gutiérrez-Uribe, Janet A; Aráiz-Hernández, Diana; Alvarez, Mario M; Serna-Saldivar, Sergio O

2014-12-01

325

Flavonol glycosides from Montcalm dark red kidney bean: implications for the genetics of seed coat color in Phaseolus vulgaris L.  

PubMed

Three flavonol glycosides were isolated and identified from the commercial dark red kidney bean (Phaseolus vulgaris L.) cultivar Montcalm. In order of highest to lowest concentration these compounds were 3',4',5,7-tetrahydroxyflavonol 3-O-beta-D-glucopyranosyl (2-->1) O-beta-D-xylopyranoside (compound 1), quercetin 3-O-beta-D-glucopyranoside (compound 2), and kaempferol 3-O-beta-D-glucopyranoside (compound 3). Compound 1 is a flavonol glycoside that has not been reported before in P. vulgaris L. These three flavonol glycosides were yellow compounds that do not contribute to the garnet red color of Montcalm seed coats. Red-colored compounds which tested positive for proanthocyanidins are most likely responsible for the red seed coat color of Montcalm. Previous work on the chemistry of the compounds produced from the multi-allelic seed coat gene series C-C(r)()-c(u) indicated that neither anthocyanins nor flavonol glycosides were detected from seed coat extracts in the presence of the c(u)() locus. However, the seed coat color genotype of Montcalm is c(u) J g B v rk(d) and three flavonol glycosides were found. Technological advances such as modern HPLC analysis of seed coat extracts may allow for detection of small amounts of compounds which previously could not be seen using paper chromatography. Alternatively, the change of the Rk allele to rk(d) may allow for the synthesis of flavonol glycosides in the presence of c(u). PMID:10552769

Beninger, C W; Hosfield, G L

1999-10-01

326

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

327

Thermaldecomposition of two synthetic glycosides by TG, DSC and simultaneous Py-GC-MSanalysis  

Microsoft Academic Search

To develop thermal stable flavor, two glycosidic\\u000a bound flavor precursors, geranyl-tetraacetyl-?-D-glucopyranoside\\u000a (GLY-A) and geranyl-?-D-glucopyranoside\\u000a (GLY-B) were synthesized by the modified Koenigs–Knorr reaction. The\\u000a thermal decomposition process and pyrolysis products of the two glycosides\\u000a were extensively investigated by thermogravimetry (TG), differential scanning\\u000a calorimeter (DSC) and on-line pyrolysis-gas chromatography mass spectroscopy\\u000a (Py-GC-MS). TG showed the T\\u000a p\\u000a of GLY-A and GLY-B were

W.-C. Xie; X.-H. Gu; Z.-C. Tan; J. Tang; G.-Y. Wang; C.-R. Luo; L.-X. Sun

2007-01-01

328

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

PubMed

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

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

2013-08-01

329

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

330

Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells.  

PubMed

4'-O-?-d-Glucopyranosyl-quercetin-3-O-?-d-glucopyranosyl-(1?4)-?-d-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis. Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-?-d-glucopyranoside (1), quercetin-3-O-?-d-glucopyranosyl-(1?4)-?-d-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. PMID:24433966

Yamauchi, Kosei; Mitsunaga, Tohru; Batubara, Irmanida

2014-02-01

331

Structures of the novel ?-glucosyl linked diterpene glycosides from Stevia rebaudiana.  

PubMed

From the commercial extract of the leaves of Stevia rebaudiana, two new minor diterpene glycosides having ?-glucosyl linkage were isolated besides the known steviol glycosides including stevioside, steviolbioside, rebaudiosides A-F, rubusoside and dulcoside A. The structures of the two compounds were identified as 13-[(2-O-(3-?-O-d-glucopyranosyl)-?-d-glucopyranosyl-3-O-?-d-glucopyranosyl-?-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid ?-d-glucopyranosyl ester (1), and 13-[(2-O-?-d-glucopyranosyl-3-O-(4-O-?-d-glucopyranosyl)-?-d-glucopyranosyl-?-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid ?-d-glucopyranosyl ester (2), on the basis of extensive NMR and MS spectral data as well as chemical studies. PMID:21798525

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

2011-09-27

332

Synthetic study on the relationship between structure and sweet taste properties of steviol glycosides.  

PubMed

The structure activity relationship between the C??-C?? methylene double bond on the aglycone of steviol glycosides and the corresponding impact on their sweet taste has been reported here for the first time. It has been observed that converting stevioside and rebaudioside A to their corresponding ketones by switching the doubly bonded methylene on C-17 for a ketone group actually removes the sweet taste properties of these molecules completely. Regenerating the original molecules tends to restore the sweet taste of both the steviol glycosides. Thus this C??-C?? methylene double bond in rebaudioside A and stevioside can be regarded as a pharmacophore essential for the sweetness property of these molecules. PMID:22481539

Upreti, Mani; Dubois, Grant; Prakash, Indra

2012-01-01

333

Chemistry and biological activity of steroidal glycosides from the Lilium genus.  

PubMed

Covering: 1989 up to 2014Plants from the Lilium genus are a rich source of chemical diversity and have been the focus of natural products chemistry research for over twenty years. This manuscript provides a background on the chemistry and nomenclature of steroidal glycosides, as well as a chronological account of the progress between the years of 1989 up to 2014, with respect to their isolation and characterization from the genus. This review highlights the traditional use of lilies, as both food and medicine, and brings attention to the fact that the genus contains 110 accepted species of which the chemistry and biological activity of the steroidal glycosides from the majority have not been investigated to date. Thus, making the genus a relatively untapped resource that contains a potential treasure trove of chemical diversity waiting to be discovered. PMID:25407469

Munafo, John P; Gianfagna, Thomas J

2015-02-26

334

New steroidal saponins and sterol glycosides from Paris polyphylla var. yunnanensis.  

PubMed

Four new steroidal saponins, pariposides A-D (1-4), and two new sterol glycosides, pariposides E-F (5-6), along with eight known steroidal saponins (7-14), two known sterol glycosides (15-16), and two known ecdysteroids (17-18), were isolated from the roots of Paris polyphylla var. yunnanensis. Among them, compounds 1-4 are the first spirostanol saponins with a peroxy group located between C-5 and C-8 of the aglycone. Their structures were determined by detailed spectroscopic analyses and chemical methods. All the isolated compounds were evaluated for their in vitro cytotoxicities against human nasopharyngeal carcinoma epithelial (CNE) cells, and steroidal saponins 7, 11, 13, and 14 showed a potent antiproliferative effect on CNE cells with IC?? values of 9.2, 4.7, 11.1, and 2.7?µM, respectively. PMID:22923196

Wu, Xia; Wang, Lei; Wang, Guo-Cai; Wang, Hui; Dai, Yi; Ye, Wen-Cai; Li, Yao-Lan

2012-10-01

335

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

SciTech Connect

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

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

1986-01-01

336

Investigation of the glycosidic linkages in several oligosaccharides using FT-IR and FT Raman spectroscopies  

NASA Astrophysics Data System (ADS)

FT-IR and FT Raman spectra of eight oligosaccharides have been recorded in the crystalline state. The FT-Raman measurements have been done in the 1500-100 cm -1 range and the FT-IR ones between 1500 and 600 cm -1. Five of these oligosaccharides are oligomers of amylose and four are oligomers of cellulose. The two series present the same monosaccharide composition which is glucose the difference between them being that maltose (the disaccharide analog of amylose) and cellobiose (the disaccharide analog of cellulose) present the different configurations of the glycosidic linkages, ? 1-4 and ? 1-4 respectively. Features were revealed that appear to be characteristic of details of the stereochemistry and bands associated with the glycosidic linkages were studied.

Sekkal, M.; Dincq, V.; Legrand, P.; Huvenne, J. P.

1995-04-01

337

Cucurbitane and hexanorcucurbitane glycosides from the fruits of Cucurbita pepo cv dayangua.  

PubMed

Phytochemical investigation of the fruits of Cucurbita pepo cv dayangua has led to the isolation of two cucurbitane glycosides: cucurbitacin L 2-O-beta-D-glucopyranoside (1), cucurbitacin K 2-O-beta-D-glucopyranoside (2) and two hexanorcucurbitane glycosides: 2,16-dihydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 2-O-beta-D-glucopyranoside (3) and 16-hydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranoside (4). Compounds 1, 2 and 3 were isolated from Cucurbita genus for the first time, while compound 4 is a new one. Their structures were determined on the basis of chemical and spectroscopic evidence. PMID:17885839

Wang, Da-Cheng; Pan, Hong-Yu; Deng, Xu-Ming; Xiang, Hua; Gao, Hui-Yuan; Cai, Hui; Wu, Li-Jun

2007-01-01

338

Pseudoglycosyltransferase Catalyzes Non-Glycosidic C-N Coupling in Validamycin A Biosynthesis  

PubMed Central

Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or non-sugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented non-glycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated ‘pseudoglycosyltransferase’ catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7?-phosphate with net retention of the ‘anomeric’ configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7?-phosphate to validoxylamine A. PMID:21766819

Asamizu, Shumpei; Yang, Jongtae; Almabruk, Khaled H.; Mahmud, Taifo

2011-01-01

339

Separation of glycosidic catiomers by TWIM-MS using CO2 as a drift gas.  

PubMed

Traveling wave ion mobility mass spectrometry (TWIM-MS) is shown to be able to separate and characterize several isomeric forms of diterpene glycosides stevioside (Stv) and rebaudioside A (RebA) that are cationized by Na(+) and K(+) at different sites. Determination and characterization of these coexisting isomeric species, herein termed catiomers, arising from cationization at different and highly competitive coordinating sites, is particularly challenging for glycosides. To achieve this goal, the advantage of using CO2 as a more massive and polarizable drift gas, over N2 , was demonstrated. Post-TWIM-MS/MS experiments were used to confirm the separation. Optimization of the possible geometries and cross-sectional calculations for mobility peak assignments were also performed. Copyright © 2015 John Wiley & Sons, Ltd. PMID:25800015

Bataglion, Giovana A; Souza, Gustavo Henrique Martins Ferreira; Heerdt, Gabriel; Morgon, Nelson H; Dutra, José Diogo Lisboa; Freire, Ricardo Oliveira; Eberlin, Marcos N; Tata, Alessandra

2015-02-01

340

Solvent Influence on Cellulose 1,4-?-Glycosidic Bond Cleavage: A Molecular Dynamics and Metadynamics Study.  

PubMed

We explore the influence of two solvents, namely water and the ionic liquid 1-ethyl-3-methylimidazolium acetate (EmimAc), on the conformations of two cellulose models (cellobiose and a chain of 40 glucose units) and the solvent impact on glycosidic bond cleavage by acid hydrolysis by using molecular dynamics and metadynamics simulations. We investigate the rotation around the glycosidic bond and ring puckering, as well as the anomeric effect and hydrogen bonds, in order to gauge the effect on the hydrolysis mechanism. We find that EmimAc eases hydrolysis through stronger solvent-cellulose interactions, which break structural and electronic barriers to hydrolysis. Our results indicate that hydrolysis in cellulose chains should start from the ends and not in the centre of the chain, which is less accessible to solvent. PMID:25689773

Loerbroks, Claudia; Boulanger, Eliot; Thiel, Walter

2015-03-27

341

Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives.  

PubMed

A series of perbutyrylated glycosides of podophyllotoxin and its derivatives were synthesized and evaluated for their antitumor activity in vitro. Most of them exhibit cytotoxic activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Among the synthesized compounds, epipodophyllotoxin ?-d-galactopyranoside 8b, epipodophyllotoxin ?-d-arabinopyranoside 8e, and podophyllotoxin ?-d-glucopyranoside 11a show the highest potency of anticancer activity with their IC50 values ranging from 0.14 to 1.69?M. Structure activity relationship analysis indicates that the type of glycosidic linkage, the configuration at C-4 of the podophyllotoxin scaffold, and the substitution at 4'-position (OH vs OCH3) can all have significant effect on the potency of their anticancer activity. Several compounds are more active than the control drugs Etoposide and Cisplatin, suggesting their potential as anticancer agents for further development. PMID:25744190

Zi, Cheng-Ting; Yang, Dan; Dong, Fa-Wu; Li, Gen-Tao; Li, Yan; Ding, Zhong-Tao; Zhou, Jun; Jiang, Zi-Hua; Hu, Jiang-Miao

2015-04-01

342

Pyridine monoterpene alkaloid formation from iridoid glycosides. A novel PMTA dimer from geniposide.  

PubMed

New pyridine monoterpene alkaloids (PMTAs) have been synthesized from the iridoid glycosides 8-epi-loganin, cornin, and antirrinoside by treatment with beta-glucosidase and aqueous NH4-OAc. The PMTA from antirrinoside contained an 8-alpha-OAc group from the opened 7,8-epoxide moiety. Treatment of genipin, the aglycone of geniposide, with HCl(g) and NH3(g) yielded the PMTA racemigerine, a known plant isolate, in which the C=C-CH2OH side chain was converted to C=C-CH3. Reaction of geniposide with beta-glucosidase and aqueous NH4OAc led to oligomeric alkaloids, but at high dilution a dimer was obtained whose structure was formally that of a Diels-Alder adduct between racemigerine and a dihydropyridine. These biomimetic semisyntheses were analyzed in terms of reaction mechanisms and the relative paucity of known plant PMTAs in comparison with the multitudinous occurrence of their presumed iridoid glycoside precursors. PMID:8984152

Frederiksen, S M; Stermitz, F R

1996-01-01

343

Reversible logic for supercomputing.  

SciTech Connect

This paper is about making reversible logic a reality for supercomputing. Reversible logic offers a way to exceed certain basic limits on the performance of computers, yet a powerful case will have to be made to justify its substantial development expense. This paper explores the limits of current, irreversible logic for supercomputers, thus forming a threshold above which reversible logic is the only solution. Problems above this threshold are discussed, with the science and mitigation of global warming being discussed in detail. To further develop the idea of using reversible logic in supercomputing, a design for a 1 Zettaflops supercomputer as required for addressing global climate warming is presented. However, to create such a design requires deviations from the mainstream of both the software for climate simulation and research directions of reversible logic. These deviations provide direction on how to make reversible logic practical.

DeBenedictis, Erik P.

2005-05-01

344

Reversible logic for supercomputing.  

SciTech Connect

This paper is about making reversible logic a reality for supercomputing. Reversible logic offers a way to exceed certain basic limits on the performance of computers, yet a powerful case will have to be made to justify its substantial development expense. This paper explores the limits of current, irreversible logic for supercomputers, thus forming a threshold above which reversible logic is the only solution. Problems above this threshold are discussed, with the science and mitigation of global warming being discussed in detail. To further develop the idea of using reversible logic in supercomputing, a design for a 1 Zettaflops supercomputer as required for addressing global climate warming is presented. However, to create such a design requires deviations from the mainstream of both the software for climate simulation and research directions of reversible logic. These deviations provide direction on how to make reversible logic practical

DeBenedictis, Erik P.

2004-12-01

345

Vasectomy reversal in humans.  

PubMed

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

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

2012-10-01

346

Vasectomy reversal in humans  

PubMed Central

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

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

2012-01-01

347

In vitro & in vivo estrogenic activity of glycoside fractions of Solanum nigrum fruit  

PubMed Central

Background & objectives: The mature fruits of Solanum nigrum contains steroidal glycosides. These are often used as vegetable and there are evidences on tribal use of these fruits as an oral contraceptive. The present study was carried out to evaluate the estrogenic potential of S. nigrum fruits by in vitro and in vivo assays. Methods: Defatted methanol extract of dried S. nigrum fruits was column fractionated and the glycoside positive fractions pooled. Definite concentrations of the fraction were used for in vitro and in vivo assays. The effect on cell viability was analyzed in MCF-7 cell lines by MTT assay followed by in vitro evaluation of estrogenicity by hydroxy apatite (HAP) binding assay. The results were further evaluated in vivo by performing uterotrophic assay in ovariectomized mouse models. Results: At low concentration (40 ?g/ml), SNGF induced a dose-dependent increase in MCF-7 cell proliferation, while higher extract concentrations (80-320 ?g/ml) caused progressive cell growth inhibition. The competitive binding assay using 3H-E2 suggests that this effect is mediated by estrogen receptor. Mouse uterotrophic assay revealed a classical uterotrophic response in ovariectomized mice in response to S. nigrum glycoside fraction (SNGF). SNGF at a dose of 100 mg/kg of body wt induced the maximum height of luminal epithelial cells which indicated an increase of 30.8 per cent over control (P<0.01) with a correlated increase in uterine wet wt (150% increase over control). Higher doses (250 and 500 mg/kg body wt) of SNGF did not induce any uterotrophic effect. Interpretation & conclusions: Our preliminary data demonstrate the hormone like activity of Solanum glycosides both in vitro and in vivo in mouse, which needs to be further explored to evaluate the possible mechanism and clinical implications. PMID:21985821

Jisha, S.; Sreeja, S.; Manjula, S.

2011-01-01

348

Positive effects of cyanogenic glycosides in food plants on larval development of the common blue butterfly.  

PubMed

Cyanogenesis is a widespread chemical defence mechanism in plants against herbivory. However, some specialised herbivores overcome this protection by different behavioural or metabolic mechanisms. In the present study, we investigated the effect of presence or absence of cyanogenic glycosides in birdsfoot trefoil (Lotus corniculatus, Fabaceae) on oviposition behaviour, larval preference, larval development, adult weight and nectar preference of the common blue butterfly (Polyommatus icarus, Lycaenidae). For oviposition behaviour there was a female-specific reaction to cyanogenic glycoside content; i.e. some females preferred to oviposit on cyanogenic over acyanogenic plants, while other females behaved in the opposite way. Freshly hatched larvae did not discriminate between the two plant morphs. Since the two plant morphs differed not only in their content of cyanogenic glycoside, but also in N and water content, we expected these differences to affect larval growth. Contrary to our expectations, larvae feeding on cyanogenic plants showed a faster development and stronger weight gain than larvae feeding on acyanogenic plants. Furthermore, female genotype affected development time, larval and pupal weight of the common blue butterfly. However, most effects detected in the larval phase disappeared for adult weight, indicating compensatory feeding of larvae. Adult butterflies reared on the two cyanogenic glycoside plant morphs did not differ in their nectar preference. But a gender-specific effect was found, where females preferred amino acid-rich nectar while males did not discriminate between the two nectar mimics. The presented results indicate that larvae of the common blue butterfly can metabolise the surplus of N in cyanogenic plants for growth. Additionally, the female-specific behaviour to oviposit preferably on cyanogenic or acyanogenic plant morphs and the female-genotype-specific responses in life history traits indicate the genetic flexibility of this butterfly species and its potential for local adaptation. PMID:18600348

Goverde, Marcel; Bazin, Alain; Kéry, Marc; Shykoff, Jacqui A; Erhardt, Andreas

2008-09-01

349

Six new triterpenoidal glycosides including two new sapogenols from Albizziae Cortex. V.  

PubMed

Six new triterpenoid glycosides called julibrosides A1-A4, B1 and C1 were isolated from Albizziae Cortex, the dried stem bark of Albizzia julibrissin Durazz. Their structures were determined based on spectral and chemical evidence. Julibrosides B1 and C1 had new sapogenols, designated julibrogenin B and C, respectively, while julibrosides A3 included N-acetyl-D-glucosamine as a sugar component. PMID:1294330

Kinjo, J; Araki, K; Fukui, K; Higuchi, H; Ikeda, T; Nohara, T; Ida, Y; Takemoto, N; Miyakoshi, M; Shoji, J

1992-12-01

350

Sedative activity of two flavonol glycosides isolated from the flowers of Albizzia julibrissin Durazz.  

PubMed

The flowers of Albizzia julibrissin are used as a sedative in oriental traditional medicine. The phytochemical study of this plant allowed the isolation of two flavonol glycosides, quercitrin (1) and isoquercitrin (2). The sedative activity of these compounds was evaluated, and both compounds 1 and 2 increased pentobarbital-induced sleeping time in dose-dependent manner in mice. These results support the use of the flowers of this plant as a sedative agent. PMID:10904180

Kang, T H; Jeong, S J; Kim, N Y; Higuchi, R; Kim, Y C

2000-07-01

351

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

352

Detailed Kinetic Analysis of a Family 52 Glycoside Hydrolase:  A ?-Xylosidase from Geobacillus stearothermophilus †  

Microsoft Academic Search

Geobacillus stearothermophilusT-6 encodes for a ‚-xylosidase (XynB2) from family 52 of glycoside hydrolases that was previously shown to hydrolyze its substrate with net retention of the anomeric configuration. XynB2 significantly prefers substrates with xylose as the glycone moiety and exhibits a typical bell-shaped pH dependence curve. Binding properties of xylobiose and xylotriose to the active site were measured using isothermal

Tsafrir Bravman; Gennady Zolotnitsky; Valery Belakhov; Gil Shoham; Bernard Henrissat; Timor Baasov; Yuval Shoham

2003-01-01

353

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

354

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

355

A new anthraquinone glycoside from the root of Rheum officinale Baill.  

PubMed

A new and a known anthraquinone glycosides were isolated from the ethanol extract of the roots of Rheum officinale Baill. The extract was purified by various chromatographies, such as silica gel, Sephadex LH-20, RP-C18 column chromatography and HPLC. Two compounds were identified by the spectroscopic techniques of NMR, MS, and chemical method. In addition, they were tested for their cytotoxic effects against HepG2 cell. Unfortunately, they showed no or weak activity. PMID:23227548

Xia, Zheng-Xiang; Tang, Zhong-Yan; An, Rui; Chen, Ye; Zhang, Yi-Zhu; Wang, Xin-Hong

2012-09-01

356

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

357

A real-time fluorogenic assay for the visualization of glycoside hydrolase activity in planta.  

PubMed

There currently exists a diverse array of molecular probes for the in situ localization of polysaccharides, nucleic acids, and proteins in plant cells, including reporter enzyme strategies (e.g. protein-glucuronidase fusions). In contrast, however, there is a paucity of methods for the direct analysis of endogenous glycoside hydrolases and transglycosidases responsible for cell wall remodeling. To exemplify the potential of fluorogenic resorufin glycosides to address this issue, a resorufin beta-glycoside of a xylogluco-oligosaccharide (XXXG-beta-Res) was synthesized as a specific substrate for in planta analysis of XEH activity. The resorufin aglycone is particularly distinguished for high sensitivity in muro assays due to a low pK(a) (5.8) and large extinction coefficient (epsilon 62,000 M(-1) cm(-1)), long-wavelength fluorescence (excitation 571 nm/emission 585 nm), and high quantum yield (0.74) of the corresponding anion. In vitro analyses demonstrated that XXXG-beta-Res is hydrolyzed by the archetypal plant XEH, nasturtium (Tropaeolum majus) NXG1, with classical Michaelis-Menten substrate saturation kinetics and a linear dependence on both enzyme concentration and incubation time. Further, XEH activity could be visualized in real time by observing the localized increase in fluorescence in germinating nasturtium seeds and Arabidopsis (Arabidopsis thaliana) inflorescent stems by confocal microscopy. Importantly, this new in situ XEH assay provides an essential complement to the in situ xyloglucan endotransglycosylase assay, thus allowing delineation of the disparate activities encoded by xyloglucan endotransglycosylase/hydrolase genes directly in plant tissues. The observation that XXXG-beta-Res is also hydrolyzed by diverse microbial XEHs indicates that this substrate, and resorufin glycosides in general, may find broad applicability for the analysis of wall restructuring by polysaccharide hydrolases during morphogenesis and plant-microbe interactions. PMID:19783642

Ibatullin, Farid M; Banasiak, Alicja; Baumann, Martin J; Greffe, Lionel; Takahashi, Junko; Mellerowicz, Ewa J; Brumer, Harry

2009-12-01

358

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

359

Simultaneous estimation of glycosidic isoflavones in fermented and unfermented soybeans by TLC-densitometric method.  

PubMed

A simple, accurate and rapid high-performance thin-layer chromatographic (HPTLC) method for the simultaneous quantification of three glycosidic isoflavones (daidzin, genistin and glycitin) in soybean (Glycine max L.) has been established and validated. Chromatography was performed on aluminum foil-backed silica gel 60 F254 HPTLC plates and found compact spots for daidzin, genistin and glycitin (Rf value of 0.39, 0.51 and 0.32, respectively) with mobile phase toluene : ethyl acetate : formic acid : acetic acid in the ratio of 1 : 8 : 1 : 0.5, v/v/v/v. Ultraviolet detection was performed densitometrically at the maximum absorbance wavelength, 260 nm. The method was validated for precision, recovery, robustness, specificity, limit of detection (LOD) and limit of quantification (LOQ), in accordance with the ICH guidelines. The LOD (2.9, 19.3 and 3.5 µg mL(-1)), LOQ (9.03, 58.6 and 10.7 µg mL(-1)), recovery (95.9-106.66, 86.97-106.56 and 98.54-105.65%) and precision (?2.12, ?0.722 and ?0.066) were satisfactory for glycosidic form of isoflavones daidzin, genistin and glycitin, respectively. Soybean variety Kh-09 bragg was found to have relatively higher amount of glycosidic isoflavones, namely daidzin, genistin and glycitin 278, 597.5 and 109.4 µg g(-1), respectively, and after fermentation the glycosidic isoflavones concentration in soybean fermented with Bacillus subtilis strain were decreased significantly after 24 h of incubation; conversely, aglycone isoflavones were increased significantly. The method for quantification of isoflavones in unfermented and fermented soybeans, with good resolution has been developed. PMID:24872524

Puri, Alka; Panda, Bibhu P

2015-02-01

360

Cardiotonic glycosides from biomass of Digitalis purpurea L. cultured in temporary immersion systems  

Microsoft Academic Search

Cardiotonic glycosides are extracted mostly from leaves of Digitalis plants. Commercial production of bioactive secondary metabolites by traditional agriculture is an inefficient process and\\u000a can be affected by climatic and soil conditions. Strategies, based on in vitro culture methods, have been extensively studied\\u000a to improve the production of specific plant derived chemicals. The aim of the present research was to

Naivy Pérez-Alonso; Dirk Wilken; André Gerth; Annett Jähn; Horst-Michael Nitzsche; Gerhard Kerns; Alina Capote-Perez; Elio Jiménez

2009-01-01

361

Euphydryas anicia (Lepidoptera: Nymphalidae) utilization of iridoid glycosides from Castilleja and Besseya (Scrophulariaceae) host plants  

Microsoft Academic Search

Iridoid glycosides were found to be sequestered by natural populations ofEuphydryas anicia after ingestion from the host plantsBesseya alpina, B. plantaginea, andCastilleja integra. Both major iridoids ofB. alpina, cataipol and aucubin, were found in butterfly populations where this was the only host plant. The catalpol-aucubin ratio was higher in the butterflies than in the host plant. AnE. anicia population which

Frank R. Stermitz; Dale R. Gardner; Francois J. Odendaal; Paul R. Ehrlich

1986-01-01

362

Host plant utilization and iridoid glycoside sequestration by Euphydryas anicia (Lepidoptera: Nymphalidae)  

Microsoft Academic Search

The iridoid glycoside content of individual adultEuphydryas anicia butterflies from two Colorado populations was quantitatively determined. At one site (Red Hill), larval host plants wereCastilleja integra andBesseya plantaginea, while at the other site (Cumberland Pass) a single host plant,B. alpina, was used. At Red Hill, macfadienoside and catalpol were sequestered, while at Cumberland Pass, catalpol and aucubin were sequestered. Artificial

Dale R. Gardner; Frank R. Stermitz

1988-01-01

363

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 Å) crystal structure has been determined, resulting in the first reported structure of a GH52 family member. A lower resolution (2.6 Å) 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

364

Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata  

PubMed Central

Three new kaempferol glycosides, named palmatosides A (1), B (2) and C (3), together with three known kaempferol glycosides, multiflorins A (4) and B (5), and afzelin (6), were isolated from the roots of the fern Neocheiropteris palmatopedata. Palmatosides A (1) and B (2) were determined to be novel kaempferol glycosides, each possessing an unusual sugar moiety containing a 4, 4-dimethyl-3-oxo-butoxy substituent group. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit tumor necrosis factor alpha (TNF-?)-induced NF-?B activity, nitric oxide (NO) production, aromatase, quinone reductase 2 (QR-2) and COX-1/-2 activities. Palmatosides B (2) and C (3) inhibited TNF-?-induced NF-?B activity with IC50 values of 15.7 and 24.1 ?M, respectively; multiflorin A (4) inhibited aromatase enzyme with an IC50 value of 15.5 ?M; afzelin (6) showed 68.3% inhibition against QR2 at a concentration of 11.5 ?g/ml; palmatoside A (1) showed 52 % inhibition against COX-1 enzyme at a concentration of 10 ?g/ml; and multiflorin B (5) showed 52 % inhibition against nitric oxide production at a concentration of 20 ?g/ml. In addition, compounds 3-6 were shown to bind QR2 enzyme using LC-MS ultrafiltration binding assay. PMID:20100622

Yang, Jian-Hong; Kondratyuk, Tamara P.; Marler, Laura E.; Qiu, Xi; Choi, Yongsoo; Cao, Hongmei; Yu, Rui; Sturdy, Megan; Pegan, Scott; Liu, Ying; Wang, Li-Qin; Mesecar, Andrew D.; Van Breemen, Richard B.; Pezzuto, John M.; Fong, Harry H. S.; Chen, Ye-Gao; Zhang, Hong-Jie

2010-01-01

365

Seasonal variation in the content of hydrolyzable tannins, flavonoid glycosides, and proanthocyanidins in oak leaves.  

PubMed

Oaks have been one of the classic model systems in elucidating the role of polyphenols in plant-herbivore interactions. This study provides a comprehensive description of seasonal variation in the phenolic content of the English oak (Quercus robur). Seven different trees were followed over the full course of the growing season, and their foliage repeatedly sampled for gallic acid, 9 individual hydrolyzable tannins, and 14 flavonoid glycosides, as well as for total phenolics, total proanthocyanidins, carbon, and nitrogen. A rare dimeric ellagitannin, cocciferin D2, was detected for the first time in leaves of Q. robur, and relationships between the chemical structures of individual tannins were used to propose a biosynthetic pathway for its formation. Overall, hydrolyzable tannins were the dominant phenolic group in leaves of all ages. Nevertheless, young oak leaves were much richer in hydrolyzable tannins and flavonoid glycosides than old leaves, whereas the opposite pattern was observed for proanthocyanidins. However, when quantified as individual compounds, hydrolyzable tannins and flavonoid glycosides showed highly variable seasonal patterns. This large variation in temporal trends among compounds, and a generally weak correlation between the concentration of any individual compound and the total concentration of phenolics, as quantified by the Folin-Ciocalteau method, leads us to caution against the uncritical use of summary quantifications of composite phenolic fractions in ecological studies. PMID:15586669

Salminen, Juha-Pekka; Roslin, Tomas; Karonen, Maarit; Sinkkonen, Jari; Pihlaja, Kalevi; Pulkkinen, Pertti

2004-09-01

366

The Moraceae-based dart poisons of South America. Cardiac glycosides of Maquira and Naucleopsis species.  

PubMed

The use of cardenolide-containing Moraceae in the dart poisons of South America is reviewed. Those prepared by the Chocó Indians of western Colombia--called niaará or kieratchi--have probably been made from the latex of Naucleopsis amara and N. glabra. In Ecuador, the Colorado Indians used N. chiguila, while the Coaiquer Indians still derive a poison from the latex of N. naga and the Cayapá Indians occasionally make use of a blowgun poison, hambi, which probably also comes from a Naucleopsis species. The Kaborí (Rio Uneiuxi Makú) Indians of north-western Brazil may have utilized Maquira coriacea, but a more recent collection documents N. mello-barretoi latex as a source of their poison. The Tikuna Indians of western Brazil included leaves and bark of N. stipularis in one of their poisons. The principal cardiac glycosides present in Maquira species are strophanthidin-based and the main ones occurring in Naucleopsis species are antiarigenin- as well as strophanthidin-based. The structures of two new glycosides, isolated from dart-poison samples, have been established as strophanthidin beta-D-glucomethylosido-D-alloside and beta-D-digitoxosido-D-alloside. The former is a major component of pakurin, the crystalline glycoside mixture prepared by Santesson in 1928 from a Chocó Indian poison. PMID:1434687

Shrestha, T; Kopp, B; Bisset, N G

1992-09-01

367

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. PMID:22563390

Sun, Yaping; Dong, Zhiqiang; Khodabakhsh, Hadie; Chatterjee, Sandip; Guo, Su

2012-01-01

368

Mechanoanions produced by mechanical fracture of bacterial cellulose: ionic nature of glycosidic linkage and electrostatic charging.  

PubMed

Mechanoanions were produced by heterogeneous scission of the glycosidic linkages of the main chain of bacterial cellulose (BC); scission was induced by mechanical fracture of the BC in a vacuum in the dark at 77 K. The mechanoanions were detected using electron-spin-trapping methods with tetracyanoethylene. The yield of mechanoanions was positively correlated with the absolute value of the change in the Mulliken atomic charge, which was used as a descriptor of the ionic nature of the glycosidic linkage. Homogeneous scission of the glycosidic linkages induced by mechanical fracture generated mechanoradicals, the electron affinity of which was estimated on the basis of the energy of the lowest unoccupied molecular orbital for the model structure of the mechanoradical. It was concluded that the electrostatic charging of BC is caused by electron transfer from mechanoanions to mechanoradicals, which have high electron affinities. The electrostatic charge density of BC in a vacuum in the dark at 77 K was estimated to be 6.00 × 10(-1) C/g. PMID:22978760

Sakaguchi, Masato; Makino, Masakazu; Ohura, Takeshi; Iwata, Tadahisa

2012-10-11

369

Effects of phenylethanoid glycosides from Digitalis purpurea L. on the expression of inducible nitric oxide synthase.  

PubMed

We have isolated four different phenylethanoid glycosides (purpureaside A, desrhamnosyl acteoside, calceolarioside B and plantainoside D) from the leaves of Digitalis purpurea (foxglove). The effects of these glycosides on activator protein-1 (AP-1)-mediated inducible nitric oxide synthase (iNOS) gene expression in the Raw264.7 macrophage cell line have been studied. Of these four glycosides, purpureaside A potently inhibited iNOS induction by lipopolysaccharide (LPS). Increase in iNOS mRNA by LPS was completely suppressed by purpureaside A. Purpureaside A did not significantly affect LPS-inducible nuclear factor-kappaB (NF-kappaB) activation or the nuclear translocation of p65. Moreover, a reporter gene assay using AP-1 specific luciferase reporter revealed that the enhanced activity of AP-1 by LPS was completely abolished in cells treated with purpureaside A. These results demonstrated that purpureaside A inhibited LPS-inducible iNOS expression in macrophages through the suppression of AP-1, but not of NF-kappaB. PMID:15969951

Oh, Jae Wook; Lee, Jeong Yong; Han, Song Hee; Moon, Young Hee; Kim, Yoon Gyoon; Woo, Eun-Rhan; Kang, Keon Wook

2005-07-01

370

Structures of acylated sucroses and an acylated flavonol glycoside and inhibitory effects of constituents on aldose reductase from the flower buds of Prunus mume.  

PubMed

Five new acylated sucroses, mumeoses K-O, and a new acylated flavonol glycoside, mumeflavonoside A, were isolated from the flower buds of Prunus mume, cultivated in Zhejiang province, China. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated acylated sucroses and flavonol glycosides on aldose reductase were also investigated. Several flavonol glycosides including mumeflavonoside A were shown to inhibit aldose reductase. PMID:23456234

Nakamura, Seikou; Fujimoto, Katsuyoshi; Matsumoto, Takahiro; Ohta, Tomoe; Ogawa, Keiko; Tamura, Haruka; Matsuda, Hisashi; Yoshikawa, Masayuki

2013-10-01

371

Inference of Reversible Languages  

Microsoft Academic Search

A famdy of efficient algorithms for referring certain subclasses of the regular languages from fmtte posttwe samples is presented These subclasses are the k-reversible languages, for k = 0, 1, 2, .... For each k there is an algorithm for finding the smallest k-reversible language containing any fimte posluve sample. It ts shown how to use this algorithm to do

Dana Angluin

1982-01-01

372

Reverse Transfer Student Study.  

ERIC Educational Resources Information Center

After a preliminary study revealed that 21% of all credit students at Santa Ana College (SAC) had previously attended a four-year institution, a further study was conducted to determine the educational interests and matriculation patterns of these reverse transfer students. A sample of 360 reverse transfer students was selected for interviews,…

Slark, Julie

373

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.

2012-08-03

374

Structures of violaceusosides C, D, E and G, sulfated triterpene glycosides from the sea cucumber Pseudocolochirus violaceus (Cucumariidae, Dendrochirotida).  

PubMed

Four new triterpene glycosides, violaceusosides C (1), D (2), E (3) and G (4) have been isolated from the sea cucumber Pseudocolochirus violaceus (Cucumariidae, Dendrochirotida). Eight known glycosides, DS-holothurin A and holothurinoside A, isolated earlier from Holothuria forskalii (order Aspidochirotida); and violaceuside A, lefevreoside C, philinopside E, intercedenside B, violaceuside II and liovilloside A isolated earlier from representatives of the family Cucumariidae, order Dendrochirotida have also been found in P. violaceus. The chemical structures of the glycosides were elucidated by 2D NMR spectroscopy and mass spectrometry. Violaceusosides C (1), D (2), E (3) and G (4) have holostane-type aglycones and tetrasaccharide linear carbohydrate chains differing in the sugar composition and the number and position of sulfate groups. Violaceusosides E (3) and G (4) are characterized by the presence of a sulfate group at C-3 of the quinovose residue that is very rare among sea cucumber glycosides. Cytotoxic activities of the glycosides 1-4 against cells of the ascite form of mouse Ehrlich carcinoma and hemolytic activities against mouse erythrocytes have been studied. Violaceusosides C (1) and D (2) demonstrated moderate cytotoxic and hemolytic effects, while violaceusosides E (3) and G (4) have more powerful activities. PMID:24689225

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

2014-03-01

375

Metabolic fate of cardiac glycosides and flavonoids upon fermentation of aqueous sea squill (Drimia maritima L.) extracts.  

PubMed

Sea squill (Drimia maritima L.) extracts have been used for centuries for the medical treatment of heart diseases. A procedure for the preparation of Drimia extracts applied for such purposes comprising a fermentation step is described in the German Homoeopathic Pharmacopoeia (GHP). However, little is known about the secondary metabolite profile of such extracts and the fate of these components upon processing and storage. Thus, in the present study sea squill extracts were monitored during fermentation and storage by HPLC-DAD-MS(n) and GC-MS to characterise and quantitate individual cardiac glycosides and phenolic compounds. For this purpose, a previously established HPLC method for the separation and quantitation of pharmacologically relevant cardiac glycosides (bufadienolides) was validated. Within 12 months of storage, total bufadienolide contents decreased by about 50%, which was attributed to microbial and plant enzyme activities. The metabolisation and degradation rates of individual bufadienolide glycosides significantly differed, which was attributed to differing structures of the aglycones. Further degradation of bufadienolide aglycones was also observed. Besides reactions well known from human metabolism studies, dehydration of individual compounds was monitored. Quantitatively predominating flavonoids were also metabolised throughout the fermentation process. The present study provides valuable information about the profile and stability of individual cardiac glycosides and phenolic compounds in fermented Drimia extracts prepared for medical applications, and expands the knowledge of cardiac glycoside conversion upon microbial fermentation. PMID:25841205

Knittel, Diana N; Stintzing, Florian C; Kammerer, Dietmar R

2015-06-10

376

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

377

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

378

Reverse Shoulder Replacement  

MedlinePLUS

Reverse Shoulder Replacement You must have Javascript enabled in your web browser. View Program Transcript Click Here to view the OR-Live, Inc. Privacy Policy and Legal Notice © 2010 OR-Live, Inc. All rights reserved.

379

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

380

Structural and Functional Analysis of a Glycoside Hydrolase Family 97 Enzyme from Bacteroides thetaiotaomicron*  

PubMed Central

SusB, an 84-kDa ?-glucoside hydrolase involved in the starch utilization system (sus) of Bacteroides thetaiotaomicron, belongs to glycoside hydrolase (GH) family 97. We have determined the enzymatic characteristics and the crystal structures in free and acarbose-bound form at 1.6Å resolution. SusB hydrolyzes the ?-glucosidic linkage, with inversion of anomeric configuration liberating the ?-anomer of glucose as the reaction product. The substrate specificity of SusB, hydrolyzing not only ?-1,4-glucosidic linkages but also ?-1,6-, ?-1,3-, and ?-1,2-glucosidic linkages, is clearly different from other well known glucoamylases belonging to GH15. The structure of SusB was solved by the single-wavelength anomalous diffraction method with sulfur atoms as anomalous scatterers using an in-house x-ray source. SusB includes three domains as follows: the N-terminal, catalytic, and C-terminal domains. The structure of the SusB-acarbose complex shows a constellation of carboxyl groups at the catalytic center; Glu532 is positioned to provide protonic assistance to leaving group departure, with Glu439 and Glu508 both positioned to provide base-catalyzed assistance for inverting nucleophilic attack by water. A structural comparison with other glycoside hydrolases revealed significant similarity between the catalytic domain of SusB and those of ?-retaining glycoside hydrolases belonging to GH27, -36, and -31 despite the differences in catalytic mechanism. SusB and the other retaining enzymes appear to have diverged from a common ancestor and individually acquired the functional carboxyl groups during the process of evolution. Furthermore, sequence comparison of the active site based on the structure of SusB indicated that GH97 included both retaining and inverting enzymes. PMID:18981178

Kitamura, Momoyo; Okuyama, Masayuki; Tanzawa, Fumiko; Mori, Haruhide; Kitago, Yu; Watanabe, Nobuhisa; Kimura, Atsuo; Tanaka, Isao; Yao, Min

2008-01-01

381

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

382

Inhibitory effects of arbutin-?-glycosides synthesized from enzymatic transglycosylation for melanogenesis  

Microsoft Academic Search

To develop a new skin whitening agent, arbutin-?-glycosides were synthesized and evaluated for their melanogenesis inhibitory\\u000a activities. Three active compounds were synthesized via the transglycosylation reaction of Thermotoga neapolitana ?-glucosidase and purified by recycling preparative HPLC. As compared with arbutin (IC50 = 6 mM), the IC50 values of these compounds were 8, 10, and 5 mM for ?-d-glucopyranosyl-(1?6)-arbutin, ?-d-glucopyranosyl-(1?4)-arbutin, and ?-d-glucopyranosyl-(1?3)-arbutin, respectively. ?-d-Glucosyl-(1?3)-arbutin also

So-Young Jun; Kyung-Min Park; Ki-Won Choi; Min Kyung Jang; Hwan Yul Kang; Sang-Hyeon Lee; Kwan-Hwa Park; Jaeho Cha

2008-01-01

383

Unusual glycosides of pyrrole alkaloid and 4?-hydroxyphenylethanamide from leaves of Moringa oleifera  

Microsoft Academic Search

Glycosides of pyrrole alkaloid (pyrrolemarumine 4?-O-?-l-rhamnopyranoside) and 4?-hydroxyphenylethanamide (marumosides A and B) were isolated from leaves of Moringa oleifera along with eight known compounds; niazirin, methyl 4-(?-l-rhamnopyranosyloxy)benzylcarbamate, benzyl ?-d-glucopyranoside, benzyl ?-d-xylopyranosyl-(1?6)-?-d-glucopyranoside, kaempferol 3-O-?-d-glucopyranoside, quercetin 3-O-?-d-glucopyranoside, adenosine and l-tryptophan. Structure elucidations were based on analyses of chemical and spectroscopic data including 1D- and 2D-NMR.

Poolsak Sahakitpichan; Chulabhorn Mahidol; Wannaporn Disadee; Somsak Ruchirawat; Tripetch Kanchanapoom

2011-01-01

384

Unusual glycosides of pyrrole alkaloid and 4'-hydroxyphenylethanamide from leaves of Moringa oleifera.  

PubMed

Glycosides of pyrrole alkaloid (pyrrolemarumine 4?-O-?-L-rhamnopyranoside) and 4'-hydroxyphenylethanamide (marumosides A and B) were isolated from leaves of Moringa oleifera along with eight known compounds; niazirin, methyl 4-(?-L-rhamnopyranosyloxy)benzylcarbamate, benzyl ?-D-glucopyranoside, benzyl ?-D-xylopyranosyl-(1?6)-?-D-glucopyranoside, kaempferol 3-O-?-D-glucopyranoside, quercetin 3-O-?-D-glucopyranoside, adenosine and L-tryptophan. Structure elucidations were based on analyses of chemical and spectroscopic data including 1D- and 2D-NMR. PMID:21439596

Sahakitpichan, Poolsak; Mahidol, Chulabhorn; Disadee, Wannaporn; Ruchirawat, Somsak; Kanchanapoom, Tripetch

2011-06-01

385

Cardiac glycoside receptors in clinical and experimental states of chronic renal failure.  

PubMed

To investigate the mechanisms leading to decreased cardiac glycoside sensitivity in uremia, digitalis receptors were characterized by [3H]-ouabain binding to mononuclear leucocytes of chronically hemodialyzed patients and to cerebral cortex membranes of partially nephrectomized rats. There were no statistically significant differences in receptor density and affinity between uremic patients and healthy control persons and between partially nephrectomized and sham operated rats. [3H]-Ouabain bound with high affinity to intact mononuclear leucocytes and to cerebral cortex membranes. However, the affinity to the cerebral cortex membrane preparation was markedly higher. PMID:3395168

Lübbecke, F; Hüting, J; Steudle, V; Kramer, W; Schütterle, G; Wizemann, V

1988-01-01

386

Teucrium polium phenylethanol and iridoid glycoside characterization and flavonoid inhibition of biofilm-forming Staphylococcus aureus.  

PubMed

The chemical composition and biofilm regulation of 15 metabolites from Teucrium polium are reported. Compounds were isolated from a CH2Cl2-MeOH extract of the aerial parts of the plant and included iridoid and phenylethanol glycosides and a monoterpenoid, together with nine known compounds. The structures were elucidated based on standard spectroscopic (UV, (1)H and (13)C NMR), 2D NMR ((1)H-(1)H COSY, HMQC, HMBC, and NOESY), and/or LC-ESIMS/MS data analyses. Inhibition of the biofilm-forming strain Staphylococcus aureus was observed with exposure to compounds 7 and 8. PMID:25524452

Elmasri, Wael A; Yang, Tianjiao; Tran, Phat; Hegazy, Mohamed-Elamir F; Hamood, Abdul N; Mechref, Yehia; Paré, Paul W

2015-01-23

387

Two new secoiridoid glycosides from the leaves of Olea europaea L.  

PubMed

Two new secoiridoid glycosides, oleuricines A (1) and B (2), together with five known triterpenoids, beta-amyrin, oleanolic acid, erythrodiol, urs-2beta,3beta-dihydroxy-12-en-28-oic acid, and beta-maslinic acid, were isolated from the EtOAc-soluble part of EtOH extract of the leaves of Olea europaea L. The structures of these compounds were elucidated by various spectroscopic methods, including intensive 1D, 2D NMR, and HR-ESI-MS techniques. PMID:20183257

Wang, Xiao-Fei; Li, Chen; Shi, Yan-Ping; Di, Duo-Long

2009-11-01

388

Smilasides M and N, two new phenylpropanoid glycosides from Smilax riparia.  

PubMed

Two new phenylpropanoid glycosides, smilasides M and N, together with the known compound 2',6'-diacetyl-3,6-diferuloylsucrose, were isolated and characterized from the roots and rhizomes of Smilax riparia A. DC. The structures of the new compounds were elucidated as 2',6'-diacetyl-3-Z-feruloyl-6-feruloylsucrose (1) and 2',6'-diacetyl-3-feruloyl-6-Z-feruloylsucrose (2) on the basis of extensive analysis of HR-ESI-MS, UV, IR, and 1D and 2D NMR spectroscopic data. PMID:22296157

Sun, Ting-Ting; Zhang, Dian-Wen; Han, Yan; Dong, Fang-Yan; Wang, Wei

2012-01-01

389

A new acylated quercetin glycoside and other secondary metabolites from Helleborus foetidus.  

PubMed

A new acylated flavonol glycoside, quercetin 3-O-(2-trans-caffeoyl)-alpha-L-arabinopyranosyl-(1-->2)-beta-D-glucopyranoside (1), together with the known 25R,26-[(beta-D-glucopyranosyl)oxy]-22alpha-hydroxy-5beta-furostan-3-beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside (2), anemonin (3), beta-D-glucosyl-p-hydroxyphenylethyl alcohol (4), and 1-beta-O-caffeoyl-D-glucose (5) were isolated from Helleborus foetidus leaves and identified on the basis of detailed spectral analysis. PMID:16545528

Prieto, Jose M; Siciliano, Tiziana; Braca, Alessandra

2006-04-01

390

Structures of two new steroidal glycosides, soladulcosides A and B from Solanum dulcamara.  

PubMed

The structures of two new steroidal glycosides named soladulcosides A and B, isolated from the aerial parts of Solanum dulcamara including new sapogenols, were elucidated as (22R, 25R)-3 beta, 15 alpha, 23 alpha-trihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside and (22R, 25R)-3 beta,23 alpha-dihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-[alpha-L-rhamnopyranosyl-(1----4)]- beta-D-glucopyranoside, respectively. PMID:1934188

Yamashita, T; Matsumoto, T; Yahara, S; Yoshida, N; Nohara, T

1991-06-01

391

Two new acylated flavonol glycosides from the seeds of Lepidium sativum.  

PubMed

Two new acylated flavonol glycosides named kaempferol-3-O-(2-O-sinapoyl)-?-D-galactopyranosyl-(1 ? 2)-?-D-glucopyranoside-7-O-?-L-rhamnopyranoside (1) and quercetin-3-O-(6-O-benzoyl)-?-D-glucopyranosyl-(1 ? 3)-?-D-galactopyranoside-7-O-?-L-rhamnopyranoside (2), were isolated together with six known compounds from the seeds of L. sativum. Their structures were elucidated on the basis of spectroscopic analysis and chemical methods. In vitro 1 and 2 inhibited nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells, with IC50 values of 25.36 and 25.08 µM, respectively. PMID:25090122

Fan, Qing-Lu; Zhu, Yin-Di; Huang, Wen-Hua; Qi, Yun; Guo, Bao-Lin

2014-01-01

392

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

393

The specific substance from Pneumococcus type 34. The configuration of the glycosidic linkages  

PubMed Central

1. The specific compound from Pneumococcus type 34 was isolated from capsular material by ion-exchange chromatography. This separated it from a substance with chemical and serological properties corresponding to those reported for C-substance. 2. The configuration of the two galactofuranosyl linkages in the repeating unit of S.34 was determined and the configurations previously assigned to the other glycosidic linkages were confirmed. 3. The dephosphorylated deacetylated repeating unit is thus O-?-d-galactofuranosyl-(1?3)-O-?-d-glucopyranosyl-(1?2)-O-?-d-galactofuranosyl-(1?3)-O-?-d-galactopyranosyl- (1?2)-ribitol. PMID:4381831

Dixon, J. R.; Buchanan, J. G.; Baddiley, J.

1966-01-01

394

Two new phenolic glycosides from Gnaphalium affine D. Don and their anti-complementary activity.  

PubMed

Two new phenolic glycosides, named gnaphaffine A and B (compounds 1 and 2), were isolated from Gnaphalium affine. together with six known compounds, including caffeic acid (3), everlastoside L (4), isorhamnetin-7-O-?-D-glucopyranoside (5), quercetin- 3-O-?-D-glucopyranoside (6), scutellarein-7-O-?-D-glucoside (7) and api-genin-7-O-?-D- glucopyranoside (8). Their structures were elucidated by spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). All compounds were evaluated for their anti-complementary activity on the classical pathway of the complement system in vitro. PMID:23823875

Li, Junli; Huang, Doudou; Chen, Wansheng; Xi, Zhongxin; Chen, Cheng; Huang, Guanghui; Sun, Lianna

2013-01-01

395

Steroidal saponins obtained by biotransformation of total furostanol glycosides from Dioscorea zingiberensis with Absidia coerulea.  

PubMed

Five new steroidal saponins (1-5) were isolated from the fermentation broth of total furostanol glycosides from tubers of Dioscorea zingiberensis C.H. Wright incubated with a fungal, Absidia coerulea AS 3.3389, along with known saponins, zingiberensis new saponin (6), deltonin (7), prosapogenin A of dioscin (8), and protobioside (9), and their structures were established by NMR spectroscopy and mass spectrometry as well as by comparison with previously reported spectral data in the literatures. The induced effects in vitro on rat platelet aggregation of all compounds were evaluated. PMID:25498025

Pang, Xu; Wen, Di; Zhao, Yang; Xiong, Cheng-Qi; Wang, Xiao-Qin; Yu, Li-Yan; Ma, Bai-Ping

2015-01-30

396

Synthesis of dihydroxyphenacyl glycosides for biological and medicinal study: ?-oxoacteoside from Paulownia tomentosa  

Microsoft Academic Search

The protected structure of ß-oxoacteoside (tomentoside A), 2-oxo-2-(3,4-dihydroxyphenyl)ethyl 3-O-(2,3,4-tri-O-acetyl-a-l-rhamnopyranosyl)-4-O-caffeoyl-ß-d-glucopyranoside 14 was synthesized in 14% overall yield in 11 steps, starting from d-glucose for biological and medicinal studies of phenylpropanoid glycosides. The first step was the preparation of a 3-O-rhamnopyranosyl disaccharide sugar core 2 from a suitably protected rhamnosyl trichloroacetimidate 10 and glucose derivative (diacetone-d-glucose 1) in 71% yield. To the

Hidenori Tozuka; Michikazu Ota; Hisayoshi Kofujita; Kouetsu Takahashi

2005-01-01

397

Two new flavonol glycosides from the leaves of Cleome chelidonii L.f.  

PubMed

From the leaves of Cleome chelidonii L.f., two new flavonol glycosides, named cleomesides A (1) and B (2), and four known compounds, quercetin 3-O-?-glucopyranosyl(1 ? 2)-?-rhamnoside-7-O-?-rhamnoside (3), ethyl ?-galactopyranoside (4), adenine (5) and glycerol monostearate (6), were isolated. The structures of all isolated compounds (1-6) were determined by NMR spectroscopy and mass spectrometry. The data of known compounds (3-6) were further compared with the reported data for these compounds. PMID:25367696

Minh, Phan Nhat; Dinh Tri, Mai; Tan Phat, Nguyen; Dat, Bui Trong; Hanh, Nguyen Ngoc; Luan, Ngo Quoc; Thanh, Ma Thi Thu; Huynh, Chung Hoang

2015-04-01

398

Verticillosides A-M: Polyoxygenated pregnane glycosides from Asclepias verticillata L.  

PubMed

As part of our ongoing effort to explore the chemical diversity of plants of the United States Midwest region, the isolation and identification of 13 pregnane glycosides named verticillosides A-M from Asclepias verticillata L. are reported. The structures of these compounds were elucidated by various spectroscopic techniques, including 1D and 2D NMR, IR, UV, and HRMS. The cytotoxicity of the isolates was evaluated against paired breast cell lines Hs578T (cancer) and Hs578Bst (normal), however, no significant growth inhibition was observed. PMID:22445072

Araya, Juan J; Binns, Franklin; Kindscher, Kelly; Timmermann, Barbara N

2012-06-01

399

27-Nor-triterpenoid glycosides from the barks of Zygophyllum fabago L  

Microsoft Academic Search

From the bark of Zygophyllum fabago L., a new 27-nor-triterpenoid glycoside, 3-O-?-d-glucopyranosyl-pyrocincholate (1), together with five known compounds, 3-O-6-deoxy-?-d-glucopyranosyl-pyrocincholate (2), quinovic acid (3), 3-O-6-deoxy-?-d-glucopyranosyl-quinovic acid (4), 3-O-?-d-glucopyranosyl- quinovic acid (5) and 3-O-6-deoxy-?-d-glucopyranosyl-cincholic acid (6), were isolated and their structures elucidated on the basis of spectroscopic data. Compounds 1, 2 and 3 showed some anti-tumour activities by MTT assay.

Yu-Lin Feng; He-Ran Li; Li-Zhen Xu; Shi-Lin Yang

2007-01-01

400

27-nor-triterpenoid glycosides from the barks of Zygophyllum fabago L.  

PubMed

From the bark of Zygophyllum fabago L., a new 27-nor-triterpenoid glycoside, 3-O-beta-D-glucopyranosyl-pyrocincholate (1), together with five known compounds, 3-O-6-deoxy-beta-D-glucopyranosyl-pyrocincholate (2), quinovic acid (3), 3-O-6-deoxy-beta-D-glucopyranosyl-quinovic acid (4), 3-O-beta-D-glucopyranosyl- quinovic acid (5) and 3-O-6-deoxy-beta-D-glucopyranosyl-cincholic acid (6), were isolated and their structures elucidated on the basis of spectroscopic data. Compounds 1, 2 and 3 showed some anti-tumour activities by MTT assay. PMID:17885836

Feng, Yu-Lin; Li, He-Ran; Xu, Li-Zhen; Yang, Shi-Lin

2007-01-01

401

Two new cytotoxic disulfated holostane glycosides from the sea cucumber Pentacta quadrangularis.  

PubMed

Two new disulfated triterpene glycosides, pentactasides B and C (1 and 2, resp.), were isolated from the sea cucumber Pentacta quadrangularis collected from the South China Sea. Their structures were elucidated by extensive spectral analysis (2D-NMR and MS) and chemical methods. The compounds 1 and 2 possess the same tetrasaccharide moieties with two sulfated groups, but are different in the side chains of the triterpene aglycone. Pentactasides B and C (1 and 2, resp.) showed significant cytotoxicities (IC(50) 0.09-2.30 microM) against different human tumor cell lines. PMID:20087982

Han, Hua; Xu, Qiang-Zhi; Yi, Yang-Hua; Gong, Wei; Jiao, Bing-Hua

2010-01-01

402

A set of two diastereomers of cyanogenic glycosides from Passiflora quadrangularis.  

PubMed

A set of two diastereomers of phenylcyano glycosides, (7S)- and (7R)-phenylcyanomethyl 1'-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (1, 2), were isolated from the methanol extract of dried vines of P. quadrangularis. The absolute configurations of the benzylic methine centers were determined mainly by the comparison of 13C NMR spectra of these compounds, prunasin (3) and sambunigrin (4), of which the last two cyanoglycosides are known to have (R)- and (S)-configurations, respectively. PMID:21922906

Saeki, Daisuke; Yamada, Takeshi; Kajimoto, Tetsuya; Muraoka, Osamu; Tanaka, Reiko

2011-08-01

403

A new phenyl glycoside from the aerial parts of Equisetum hyemale.  

PubMed

A new phenyl glycoside, 2-(sophorosyl)-1-(4-hydroxyphenyl)ethanone (9), was isolated from the ethanolic extract of the aerial parts of Equisetum hyemale L., together with eight known compounds (1-8). The structures of these compounds were elucidated using a combination of spectroscopic analyses and chemical method. Of these nine compounds, 4 and 7 showed hepatoprotective effects towards tacrine-induced cytotoxicity in Hep 3B cells with EC50 values of 42.7 ± 1.5 and 132.6 ± 2.8 ?M, respectively. PMID:25117054

Jin, Mei; Zhang, Changhao; Zheng, Tie; Yao, Dalei; Shen, Le; Luo, Jie; Jiang, Zhe; Ma, Juan; Jin, Xue-Jun; Cui, Jiongmo; Lee, Jung Joon; Li, Gao

2014-01-01

404

Stability of black cohosh triterpene glycosides and polyphenols: potential clinical relevance.  

PubMed

Concurrent to a clinical trial of black cohosh for menopausal hot flashes, the long-term stability of the black cohosh, over the duration of the clinical trial, was examined. Analytical results showed that the major constituents, both triterpene glycosides and polyphenols, were stable over the 3-year period of testing. These results indicate that a black cohosh product stored for several years in a controlled environment does not undergo significant changes in its major constituents. These results have implications not only for clinical research in natural products, but for basic science, as well as the dietary supplements industry. PMID:23415548

Jiang, Bei; Kronenberg, Fredi; Balick, Michael J; Kennelly, Edward J

2013-04-15

405

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. PMID:24759001

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

406

Iridoid glycoside sequestration by two aposematicPenstemon-feeding geometrid larvae.  

PubMed

The iridoid glycoside catalpol was found to be sequestered by larvae ofMeris alticola feeding onPenstemon virgatus and by larvae ofNeoterpes graefiaria which utilizeP. barbatus. The strikingly similar larval patterns of these two ennomine geometrids were previously considered to be disruptive, but predator-based Mullerian mimicry is equally likely to be involved. The cryptic adult moths generally contain only small amounts of catalpol, having left most of the bitter iridoid in the pupal case and in the meconium excreted after eclosion. OneNeoterpes female did contain considerable catalpol in the abdomen, presumably in the eggs. PMID:24275990

Stermitz, F R; Gardner, D R; McFarland, N

1988-02-01

407

Antioxidant and anti-inflammatory caffeoyl phenylpropanoid and secoiridoid glycosides from Jasminum nervosum stems, a Chinese folk medicine.  

PubMed

Eight compounds including four caffeoyl phenylpropanoid glycosides, jasnervosides A-D (1-4), one monoterpenoid glycoside, jasnervoside E (5), and three secoiridoid glycosides, jasnervosides F-H (10-12), were isolated from the stems of Jasminum nervosum Lour. (Oleaceae), along with four known compounds, poliumoside (6), verbascoside (7), ?-l-rhamnopyranosyl-(1?3)-O-(?-l-rhamnopyranosyl(1?6)-1-O-E-caffeoyl-?-d-glucopyranoside (8), and jaspolyanthoside (9). Their structures were elucidated on the basis of their physicochemical and spectroscopic properties. Compounds 1, 2, 4 and 11 displayed potent antioxidant activities in the DPPH assay, while 2 and 3 displayed good activities against LPS-induced TNF-? and IL-1? production in BV2 cells. Compounds 1-5 and 10-12 were evaluated for their cytotoxic activities against three human cancer cell lines (A-549, Bel-7402, and HCT-8), but none displayed significant activity. PMID:25107663

Guo, Zhi-Yong; Li, Ping; Huang, Wen; Wang, Jian-Jun; Liu, Yu-Jing; Liu, Bo; Wang, Ye-Ling; Wu, Shi-Biao; Kennelly, Edward J; Long, Chun-Lin

2014-10-01

408

Quantitative analysis of cycloartane glycosides in black cohosh rhizomes and dietary supplements by RRLC-ELSD and RRLC-qTOF-MS.  

PubMed

In this study, a fast and reproducible RRLC-ELSD method for the quantitative analysis of 17 cycloartane glycosides and the aglycone cimigenol in black cohosh rhizomes and dietary supplements has been developed. Separation of the 18 triterpenes was achieved within 16 min using reversed phase material and a gradient elution system consisting of water, acetonitrile and methanol. The method was validated for accuracy (recovery rates from 96.79% to 102.86%), precision (intra-day variation ?5.98%, inter-day variation ?3.74%), repeatability (R.S.D.???6.94%) and sensitivity, with detection limits below 4.0 ?g/mL and quantification limits lower than 13.2 ?g/mL. Calibration curves were established in the range from 5-1,000 ?g/mL, with correlation coefficients higher than 0.998 for all constituents investigated. Peak purity and peak assignment were confirmed by means of RRLC-qTOF-MS and in comparison with reference compounds. Three different MS sources (ESI, APCI and APPI) were compared for their ionisation potential regarding cycloartane derivatives. One of the isolated black cohosh constituents, 24-O-acetylhydroshengmanol-3-O-?-L-arabinopyranoside, could be identified as new natural compound. PMID:20694806

Cicek, Serhat S; Aberham, Anita; Ganzera, Markus; Stuppner, Hermann

2011-06-01

409

Phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala and their F1 hybrids: not all hybrids are created equal  

Microsoft Academic Search

The performance of hybrids depends upon the inheritance and expression of resistance traits. Secondary chemicals are one such resistance trait. In this study, we measured the concentrations of phenolic glycosides and condensed tannins in parental and F1 hybrid willows to examine the sources of chemical variation among hybrids. S. sericea produces phenolic glycosides, salicortin and 2?-cinnamoylsalicortin, and low concentrations of

Colin M. Orians; Megan E Griffiths; Bernadette M. Roche; Robert S. Fritz

2000-01-01

410

Identification of Flavonoid Glycosides in Rosa chinensis Flowers by Liquid Chromatography-tandem Mass Spectrometry in Combination with 13C Nuclear Magnetic Resonance  

PubMed Central

Flowers of Rosa chinensis are widely used in traditional Chinese medicine as well as in food industry. Flavonoid glycosides are believed to be the major components in R. chinensis that are responsible for its antioxidant activities. In this work, a liquid chromatography-tandem mass spectrometry (HPLC- MS/MS) method was developed for analysis of flavonoid glycosides presented in ethyl acetate extract of dried R. chinensis flowers. Twelve flavonoid glycosides were separated and detected. By comparing the retention times, UV spectra, and tandem MS fragments with those of respective authentic compounds, eight flavonoid glycosides were unequivocally identified. Although the other four were also identified as flavonoid glycosides, the glycosylation positions could not be determined due to lack of authentic compounds. Fortunately, the glycosylation effects were clearly observed in the 13C NMR spectrum of the extract. The detailed structural information was, therefore, obtained to identify the four flavonoid glycosides as quercetin-3-O-D-glucoside, quercetin-3-O-D-xyloside, kaempferol-3-O-D-xyloside and quercetin-3-O-D-(6?-coumaroyl)-galactoside. These flavonoid glycosides were detected and identified for the first time in this botanic material. This work reports on the first use of 13C NMR of a mixture to enhance a rapid HPLC-MS/MS analysis. The proposed analytical protocol was validated with a mixture of authentic flavonoid glycosides. PMID:22749452

Qing, Lin-Sen; Xue, Ying; Zhang, Jian-Guang; Zhang, Zhi-Feng; Liang, Jian; Jiang, Yan; Liu, Yi-Ming; Liao, Xun

2012-01-01

411

Systemic, Genotype-Specific Induction of Two Herbivore-Deterrent Iridoid Glycosides in Plantago lanceolata L. in Response to Fungal Infection by Diaporthe adunca (Rob.) Niessel  

Microsoft Academic Search

Iridoid glycosides are a group of terpenoid secondary plant compounds known to deter generalist insect herbivores. In ribwort plantain (Plantago lanceolata), the iridoid glycosides aucubin and catalpol can be induced following damage by insect herbivores. In this study, we investigated whether the same compounds can be induced following infection by the fungal pathogen Diaporthe adunca, the causal agent of a

Hamida B. Marak; Arjen Biere; Jos M. M. Van Damme

2002-01-01

412

Effect of harvest timing on leaf production and yield of diterpene glycosides in Stevia rebaudiana Bert: a specialty perennial crop for Mississippi  

Technology Transfer Automated Retrieval System (TEKTRAN)

Stevia rebaundiana (Bertoni), a perennial shrub of the Asteraceae, is one of the most important sources of non-caloric natural sweeteners. Stevia’s plant extracts and glycosides have been used for several years in Paraguay and Brazil. Several studies suggest that Stevia and its glycosides exert ben...

413

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. PMID:21814831

2012-01-01

414

Gas-phase intramolecular elimination reaction studies of steviol glycosides in positive electrospray and tandem mass spectrometry.  

PubMed

This paper reports the first study of the gas-phase intramolecular elimination reaction of steviol glycosides in positive electrospray mass spectrometry. The observed glycosylated product ions are proposed to be formed via an intramolecular elimination of sugar units from the parent molecule ion. It was further proven by MS/MS studies and deuterium labeling experiments with one of the steviol glycosides, rebaudioside A. These mass spectrometric results confirmed that the new glycosylated product ions observed are most likely formed by the combination of glucose moieties (Glu) II-IV and Glu I via a gas-phase intramolecular elimination reaction. PMID:19174590

Upreti, Mani; Clos, John F; Somayajula, Kasi V; Milanowski, Dennis J; Mocek, Ulla; Dubois, Grant E; Prakash, Indra

2009-01-01

415

Conformational Properties of Nucleotide-Based Template-Competitive HIV1 Reverse Transcriptase Inhibitors: Analysis of Enzyme Binding Modes  

Microsoft Academic Search

Nucleotides 2-(4-azidophenacyl)thio-1,N-etheno-2?-deoxyadenosine 5?-triphosphate 1 and its tetrafluoro analog 2 inhibit HIV-1 reverse transcriptase (RT) competitively relative to template. These template-competitive RT inhibitors (TCRTIs) were analyzed for conformational properties by molecular modeling and NMR analysis. Both inhibitors prefer sugar conformations of C2?-endo\\/C3?-exo with a high-anti glycosidic bond rotation and +sc\\/ap phosphate conformation (?). The major effect of the etheno group is

Weiying Lin; Ke Li; Bob M. Moore II; Michael B. Doughty

2003-01-01

416

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

417

Anti-oxidative and anti-inflammatory activities of caffeoyl hemiterpene glycosides from Spiraea prunifolia.  

PubMed

Activity guided isolation of a Spiraea prunifolia extract yielded five caffeoyl hemiterpene glycosides: 4'-(6-O-caffeoyl-?-D-glucopyranosyl)-2'-methyl butyric acid, 1-O-caffeoyl-6-O-(4'-hydroxy-2'-methylene-butyroyl)-?-D-glucopyranoside, 1,2-O-dicaffeoyl-6-O-(4'-hydroxy-2'-methylene-butyroyl)-?-D-glucopyranoside, 1-O-caffeoyl-6-O-(4'-caffeoyl-2'-methylene-butyroyl)-?-D-glucopyranoside, and 1-O-caffeoyl-6-O-(4'-caffeoyl-3'-hydroxy-2'-methylene-butyroyl)-?-D-glucopyranoside, and nine known compounds. Structures were elucidated by analysis of 1D and 2D NMR spectra and FAB-MS. To evaluate the anti-oxidative and anti-inflammatory properties of all fourteen compounds, DPPH radical scavenging, NBT superoxide scavenging, and inhibition of nitric oxide production in LPS-stimulated RAW264.7 cells were examined. Three of the caffeoyl hemiterpene glycosides exhibited potent anti-oxidative and anti-inflammatory activities compared with Vitamin C and l-NMMA, which were used as positive controls. PMID:24161492

Park, Sang Hee; Park, Kwan Hee; Oh, Myeong Hwan; Kim, Han Hyuk; Choe, Kang In; Kim, So Ra; Park, Kwang Jun; Lee, Min Won

2013-12-01

418

Biogenesis of C-glycosyl flavones and profiling of flavonoid glycosides in lotus (Nelumbo nucifera).  

PubMed

Flavonoids in nine tissues of Nelumbo nucifera Gaertner were identified and quantified by high-performance liquid chromatography with diode array detector (HPLC-DAD) and HPLC-electrospray ionization-mass spectrometry (HPLC-ESI-MSn). Thirty-eight flavonoids were identified; eleven C-glycosides and five O-glycosides were discovered for the first time in N. nucifera. Most importantly, the C-glycosyl apigenin or luteolin detected in lotus plumules proved valuable for deep elucidation of flavonoid composition in lotus tissues and for further utilization as functional tea and medicine materials. Lotus leaves possessed the significantly highest amount of flavonoids (2.06E3±0.08 mg 100 g(-1) FW) and separating and purifying the bioactive compound, quercetin 3-O-glucuronide, from leaves showed great potential. In contrast, flavonoids in flower stalks, seed coats and kernels were extremely low. Simultaneously, the optimal picking time was confirmed by comparing the compound contents in five developmental phases. Finally, we proposed the putative flavonoid biosynthesis pathway in N. nucifera. PMID:25279809

Li, Shan-Shan; Wu, Jie; Chen, Li-Guang; Du, Hui; Xu, Yan-Jun; Wang, Li-Jing; Zhang, Hui-Jin; Zheng, Xu-Chen; Wang, Liang-Sheng

2014-01-01

419

Targeted Discovery of Glycoside Hydrolases from a Switchgrass-Adapted Compost Community  

PubMed Central

Development of cellulosic biofuels from non-food crops is currently an area of intense research interest. Tailoring depolymerizing enzymes to particular feedstocks and pretreatment conditions is one promising avenue of research in this area. Here we added a green-waste compost inoculum to switchgrass (Panicum virgatum) and simulated thermophilic composting in a bioreactor to select for a switchgrass-adapted community and to facilitate targeted discovery of glycoside hydrolases. Small-subunit (SSU) rRNA-based community profiles revealed that the microbial community changed dramatically between the initial and switchgrass-adapted compost (SAC) with some bacterial populations being enriched over 20-fold. We obtained 225 Mbp of 454-titanium pyrosequence data from the SAC community and conservatively identified 800 genes encoding glycoside hydrolase domains that were biased toward depolymerizing grass cell wall components. Of these, ?10% were putative cellulases mostly belonging to families GH5 and GH9. We synthesized two SAC GH9 genes with codon optimization for heterologous expression in Escherichia coli and observed activity for one on carboxymethyl cellulose. The active GH9 enzyme has a temperature optimum of 50°C and pH range of 5.5 to 8 consistent with the composting conditions applied. We demonstrate that microbial communities adapt to switchgrass decomposition using simulated composting condition and that full-length genes can be identified from complex metagenomic sequence data, synthesized and expressed resulting in active enzyme. PMID:20098679

Allgaier, Martin; Reddy, Amitha; Park, Joshua I.; Ivanova, Natalia; D'haeseleer, Patrik; Lowry, Steve; Sapra, Rajat; Hazen, Terry C.; Simmons, Blake A.; VanderGheynst, Jean S.; Hugenholtz, Philip

2010-01-01

420

Comparative Analysis of Glycoside Hydrolases Activities from Phylogenetically Diverse Marine Bacteria of the Genus Arenibacter  

PubMed Central

A total of 16 marine strains belonging to the genus Arenibacter, recovered from diverse microbial communities associated with various marine habitats and collected from different locations, were evaluated in degradation of natural polysaccharides and chromogenic glycosides. Most strains were affiliated with five recognized species, and some presented three new species within the genus Arenibacter. No strains contained enzymes depolymerizing polysaccharides, but synthesized a wide spectrum of glycosidases. Highly active ?-N-acetylglucosaminidases and ?-N-acetylgalactosaminidases were the main glycosidases for all Arenibacter. The genes, encoding two new members of glycoside hydrolyses (GH) families, 20 and 109, were isolated and characterized from the genomes of Arenibacter latericius. Molecular genetic analysis using glycosidase-specific primers shows the absence of GH27 and GH36 genes. A sequence comparison with functionally-characterized GH20 and GH109 enzymes shows that both sequences are closest to the enzymes of chitinolytic bacteria Vibrio furnissii and Cellulomonas fimi of marine and terrestrial origin, as well as human pathogen Elisabethkingia meningoseptica and simbionts Akkermansia muciniphila, gut and non-gut Bacteroides, respectively. These results revealed that the genus Arenibacter is a highly taxonomic diverse group of microorganisms, which can participate in degradation of natural polymers in marine environments depending on their niche and habitat adaptations. They are new prospective candidates for biotechnological applications due to their production of unique glycosidases. PMID:23752354

Bakunina, Irina; Nedashkovskaya, Olga; Balabanova, Larissa; Zvyagintseva, Tatyana; Rasskasov, Valery; Mikhailov, Valery

2013-01-01

421

Rapid differentiation of isobaric and positional isomers of structurally related glycosides from Phytolacca bogotensis.  

PubMed

Through the action of glycosyltransferases, a plant can biosynthetically assemble small different aglycons or 'templates' to various polysaccharides to produce numerous glycoconjugates differing in the type of the attached aglycon, the anomeric configuration of C-1 of the glycosylating sugar, the type of sugar and the different position of attachments of the sugar unit present in the polysaccharide chain. The position of attachments and the anomeric configuration of the different sugar present in the polysaccharide create the opportunity to generate molecules with either the same or very close molecular weights, which have relative structural similarity--forming isobaric and positional isomers. Although isomeric differentiation was once considered outside of the domain of mass spectrometry, this task can now be resolved using tandem mass spectrometry. In a standardized purified glycoconjugate fraction (SPT01) from Phytolacca bogotensis, we report conventional electrospray ionization mass spectrometry and collision-induced dissociation (CID) MS/MS parameters which favored the formation of characteristic product ions. This allowed us to suggest the type of sugar linkages present in a specific glycoconjugate. Ten new glycoconjugate are described from this plant and another twelve known saponins were structurally characterized using the automatic MSn acquisition mode. The differentiation of two pairs of positional isomers and four isobaric glycosides and the production of a library of 30 glycosides present in P. bogotensis were accomplished. PMID:19785003

Montoya, Guillermo; Arango, Gabriel J; Ramírez-Pineda, José R

2009-11-01

422

Production of oleanolic acid glycosides by hairy root established cultures of Calendula officinalis L.  

PubMed

In order to initiate hairy root culture initiation cotyledons and hypocotyls of Calendula officinalis L. were infected with Agrobacterium rhizogenes strain ATCC 15834 or the same strain containing pCAMBIA 1381Z vector with ?-glucuronidase reporter gene under control of promoter of NIK (Nematode Induced Kinase) gene. The efficiency of induction of hairy roots reached 33.8% for cotyledons and 66.6% for hypocotyls together for both transformation experiments. Finally, eight control and nine modified lines were established as a long-term culture. The hairy root cultures showed the ability to synthesize oleanolic acid mainly (97%) as glycosides; control lines contained it at the average 8.42 mg ? g(-1) dry weight in tissue and 0.23 mg ? dm(-3) in medium; modified lines: 4.59 mg ? g(-1) for the tissue, and 0.48 mg ? dm(-3) for the medium. Additionally lines showed high positive correlation between dry/fresh weight and oleanolic acid concentration in tissue. Using the Killiani mixture in acidic hydrolysis of oleanolic acid glycosides released free aglycones that were partially acetylated in such conditions. PMID:24040627

D?ugosz, Marek; Wiktorowska, Ewa; Wi?niewska, Anita; P?czkowski, Cezary

2013-01-01

423

Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities.  

PubMed

The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, two pentane-2,4-diol glucosides, seven phenolic compounds, and three sugars, were isolated. The structures of five triterpene glycosides were elucidated on the basis of spectroscopic and chemical methods. Upon evaluation of the bioactivity of the isolated compounds, it was found that some or most of the compounds have potent or moderate inhibitory activities against the following: melanogenesis in B16 melanoma cells induced by ?-melanocyte-stimulating hormone (?-MSH); generation of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-teradecanoylphorbol 13-acetate (TPA) in Raji cells; t TPA-induced inflammation in mice, and proliferation of one or more of HL-60, A549, AZ521, and SK-BR-3 human cancer cell lines, respectively. Western blot analysis established that paradoxoside E inhibits melanogenesis by regulation of expression of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1) and TRP-2. In addition, tieghemelin A was demonstrated to exhibit cytotoxic activity against A549 cells (IC50 13.5 ?M) mainly due to induction of apoptosis by flow cytometry. The extract of defatted shea kernels and its constituents may be, therefore, valuable as potential antioxidant, anti-inflammatory, skin-whitening, chemopreventive, and anticancer agents. PMID:25446237

Zhang, Jie; Kurita, Masahiro; Shinozaki, Takuro; Ukiya, Motohiko; Yasukawa, Ken; Shimizu, Naoto; Tokuda, Harukuni; Masters, Eliot T; Akihisa, Momoko; Akihisa, Toshihiro

2014-12-01

424

Urinary pharmacokinetics of cyanidin glycosides in healthy young men following consumption of elderberry juice.  

PubMed

We investigated the urinary pharmacokinetics of monomeric anthocyanins in seven healthy volunteers. The volunteers were administered a single oral dose of 3.57 g total anthocyanins contained in 150 ml of a concentrated elderberry juice under fasting conditions. Within 24 h the urinary excretion of unchanged cyanidin-3,5-diglucoside (cyanidin-3-sambubioside-5-glucoside and cyanidin-3,5-diglucoside were calculated as cyanidin-3,5-diglucoside equivalents), cyanidin-3-glucoside, cyanidin-3-sambubioside and total anthocyanins (i.e., the sum of all quantifiable anthocyanidin glycosides) was 0.16, 0.06, 0.05 and 0.06% of the administered doses, respectively. Maximum excretion rates were determined within 1.0 h after intake. The estimates (arithmetic mean +/- SD) of t1/2 were 1.25 +/- 0.25, 1.53 +/- 0.36, 1.38 +/- 0.20 and 1.35 +/- 0.18 h for cyanidin-3,5-diglucoside, cyanidin-3-glucoside, cyanidin-3-sambubioside and total anthocyanins, respectively. The urinary excretion of intact anthocyanins was fast and the decline of excretion rates appeared to be monophasic, suggesting a one-compartment pharmacokinetic model. The low urinary excretion of dietary anthocyanidin glycosides with values below 1% indicates that a large proportion of these plant pigments consumed are metabolized before entry into the circulation. PMID:16060394

Frank, T; Sonntag, S; Strass, G; Bitsch, I; Bitsch, R; Netzel, M

2005-01-01

425

Response surface methodology to optimise Accelerated Solvent Extraction of steviol glycosides from Stevia rebaudiana Bertoni leaves.  

PubMed

Following the approval of steviol glycosides as a food additive in Europe in December 2011, large-scale stevia cultivation will have to be developed within the EU. Thus there is a need to increase the efficiency of stevia evaluation through germplasm enhancement and agronomic improvement programs. To address the need for faster and reproducible sample throughput, conditions for automated extraction of dried stevia leaves using Accelerated Solvent Extraction were optimised. A response surface methodology was used to investigate the influence of three factors: extraction temperature, static time and cycle number on the stevioside and rebaudioside A extraction yields. The model showed that all the factors had an individual influence on the yield. Optimum extraction conditions were set at 100 °C, 4 min and 1 cycle, which yielded 91.8% ± 3.4% of total extractable steviol glycosides analysed. An additional optimisation was achieved by reducing the grind size of the leaves giving a final yield of 100.8% ± 3.3%. PMID:25053094

Jentzer, Jean-Baptiste; Alignan, Marion; Vaca-Garcia, Carlos; Rigal, Luc; Vilarem, Gérard

2015-01-01

426

Pretreatment of baicalin and wogonoside with glycoside hydrolase: A promising approach to enhance anticancer potential  

PubMed Central

Previous phytochemical studies showed that the major flavonoids in Scutellaria baicalensis are baicalin, baicalein, wogonoside and wogonin. The two glycosides (baicalin and wogonoside) can be transformed into their aglycons (baicalein and wogonin), which possess positive anticancer potential. In this study, we used glycosidase to catalyze flavonoids in S. baicalensis to enhance the herb’s anticancer activities. Our HPLC data showed that, using the optimized conditions obtained in our experiments (20 U/g of cellulase, 50ºC, pH 4.8 and treatment for 8 h), there was a marked transformation from the two glycosides to their aglycons. The anticancer activity was subsequently evaluated using a series of S. baicalensis extracts in which variable lengths of glycosidase treatment time were used. Combining analytical and bioassay results, we observed that the higher the aglycon content, the stronger the antiproliferation effects. Compared to the untransformed control, 8 h of glycosidase catalyzing significantly increased antiproliferative activity on human colorectal and breast cancer cells, and its cancer cell growth inhibition is, in part, mediated by cell cycle arrest at the S-phase and induction of apoptosis. Data from this study suggest that using glycosidase to catalyze S. baicalensis offers a promising approach to increase its anticancer activity. PMID:24026776

YU, CHUNHAO; ZHANG, ZHIYU; ZHANG, HAIJIANG; ZHEN, ZHONG; CALWAY, TYLER; WANG, YUNWEI; YUAN, CHUN-SU; WANG, CHONG-ZHI

2013-01-01

427

Targeted discovery of glycoside hydrolases from a switchgrass-adapted compost community  

SciTech Connect

Development of cellulosic biofuels from non-food crops is currently an area of intense research interest. Tailoring depolymerizing enzymes to particular feedstocks and pretreatment conditions is one promising avenue of research in this area. Here we added a green-waste compost inoculum to switchgrass (Panicum virgatum) and simulated thermophilic composting in a bioreactor to select for a switchgrass-adapted community and to facilitate targeted discovery of glycoside hydrolases. Small-subunit (SSU) rRNA-based community profiles revealed that the microbial community changed dramatically between the initial and switchgrass-adapted compost (SAC) with some bacterial populations being enriched over 20-fold. We obtained 225 Mbp of 454-titanium pyrosequence data from the SAC community and conservatively identified 800 genes encoding glycoside hydrolase domains that were biased toward depolymerizing grass cell wall components. Of these, {approx}10% were putative cellulases mostly belonging to families GH5 and GH9. We synthesized two SAC GH9 genes with codon optimization for heterologous expression in Escherichia coli and observed activity for one on carboxymethyl cellulose. The active GH9 enzyme has a temperature optimum of 50 C and pH range of 5.5 to 8 consistent with the composting conditions applied. We demonstrate that microbial communities adapt to switchgrass decomposition using simulated composting condition and that full-length genes can be identified from complex metagenomic sequence data, synthesized and expressed resulting in active enzyme.

Allgaier, M.; Reddy, A.; Park, J. I.; Ivanova, N.; D'haeseleer, P.; Lowry, S.; Sapra, R.; Hazen, T.C.; Simmons, B.A.; VanderGheynst, J. S.; Hugenholtz, P.

2009-11-15

428

Targeted Discovery of Glycoside Hydrolases from a Switchgrass-Adapted Compost Community  

SciTech Connect

Development of cellulosic biofuels from non-food crops is currently an area of intense research interest. Tailoring depolymerizing enzymes to particular feedstocks and pretreatment conditions is one promising avenue of research in this area. Here we added a green-waste compost inoculum to switchgrass (Panicum virgatum) and simulated thermophilic composting in a bioreactor to select for a switchgrass-adapted community and to facilitate targeted discovery of glycoside hydrolases. Smallsubunit (SSU) rRNA-based community profiles revealed that the microbial community changed dramatically between the initial and switchgrass-adapted compost (SAC) with some bacterial populations being enriched over 20-fold. We obtained 225 Mbp of 454-titanium pyrosequence data from the SAC community and conservatively identified 800 genes encoding glycoside hydrolase domains that were biased toward depolymerizing grass cell wall components. Of these, ,10percent were putative cellulasesmostly belonging to families GH5 and GH9. We synthesized two SAC GH9 genes with codon optimization for heterologous expression in Escherichia coli and observed activity for one on carboxymethyl cellulose. The active GH9 enzyme has a temperature optimum of 50uC and pH range of 5.5 to 8 consistent with the composting conditions applied. We demonstrate that microbial communities adapt to switchgrass decomposition using simulated composting condition and that full-length genes can be identified from complex metagenomic sequence data, synthesized and expressed resulting in active enzyme.

Reddy, Amitha; Allgaier, Martin; Park, Joshua I.; Ivanoval, Natalia; Dhaeseleer, Patrik; Lowry, Steve; Sapra, Rajat; Hazen, Terry C.; Simmons, Blake A.; VanderGheynst, Jean S.; Hugenholtz, Philip

2011-05-11

429

Crystal Structure and Characterization of the Glycoside Hydrolase Family 62 ?-l-Arabinofuranosidase from Streptomyces coelicolor*  

PubMed Central

?-l-Arabinofuranosidase, which belongs to the glycoside hydrolase family 62 (GH62), hydrolyzes arabinoxylan but not arabinan or arabinogalactan. The crystal structures of several ?-l-arabinofuranosidases have been determined, although the structures, catalytic mechanisms, and substrate specificities of GH62 enzymes remain unclear. To evaluate the substrate specificity of a GH62 enzyme, we determined the crystal structure of ?-l-arabinofuranosidase, which comprises a carbohydrate-binding module family 13 domain at its N terminus and a catalytic domain at its C terminus, from Streptomyces coelicolor. The catalytic domain was a five-bladed ?-propeller consisting of five radially oriented anti-parallel ?-sheets. Sugar complex structures with l-arabinose, xylotriose, and xylohexaose revealed five subsites in the catalytic cleft and an l-arabinose-binding pocket at the bottom of the cleft. The entire structure of this GH62 family enzyme was very similar to that of glycoside hydrolase 43 family enzymes, and the catalytically important acidic residues found in family 43 enzymes were conserved in GH62. Mutagenesis studies revealed that Asp202 and Glu361 were catalytic residues, and Trp270, Tyr461, and Asn462 were involved in the substrate-binding site for discriminating the substrate structures. In particular, hydrogen bonding between Asn462 and xylose at the nonreducing end subsite +2 was important for the higher activity of substituted arabinofuranosyl residues than that for terminal arabinofuranoses. PMID:24482228

Maehara, Tomoko; Fujimoto, Zui; Ichinose, Hitomi; Michikawa, Mari; Harazono, Koichi; Kaneko, Satoshi

2014-01-01

430

BDNF mediates neuroprotection against oxygen-glucose deprivation by the cardiac glycoside oleandrin.  

PubMed

We have previously shown that the botanical drug candidate PBI-05204, a supercritical CO2 extract of Nerium oleander, provides neuroprotection in both in vitro and in vivo brain slice-based models for focal ischemia (Dunn et al., 2011). Intriguingly, plasma levels of the neurotrophin BDNF were increased in patients treated with PBI-05204 in a phase I clinical trial (Bidyasar et al., 2009). We thus tested the hypothesis that neuroprotection provided by PBI-05204 to rat brain slices damaged by oxygen-glucose deprivation (OGD) is mediated by BDNF. We found, in fact, that exogenous BDNF protein itself is sufficient to protect brain slices against OGD, whereas downstream activation of TrkB receptors for BDNF is necessary for neuroprotection provided by PBI-05204, using three independent methods. Finally, we provide evidence that oleandrin, the principal cardiac glycoside component of PBI-05204, can quantitatively account for regulation of BDNF at both the protein and transcriptional levels. Together, these findings support further investigation of cardiac glycosides in providing neuroprotection in the context of ischemic stroke. PMID:24431454

Van Kanegan, Michael J; He, Dong Ning; Dunn, Denise E; Yang, Peiying; Newman, Robert A; West, Anne E; Lo, Donald C

2014-01-15

431

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 neuroprotection in both in vitro and in vivo brain slice-based models for focal ischemia (Dunn et al., 2011). Intriguingly, plasma levels of the neurotrophin BDNF were increased in patients treated with PBI-05204 in a phase I clinical trial (Bidyasar et al., 2009). We thus tested the hypothesis that neuroprotection provided by PBI-05204 to rat brain slices damaged by oxygen-glucose deprivation (OGD) is mediated by BDNF. We found, in fact, that exogenous BDNF protein itself is sufficient to protect brain slices against OGD, whereas downstream activation of TrkB receptors for BDNF is necessary for neuroprotection provided by PBI-05204, using three independent methods. Finally, we provide evidence that oleandrin, the principal cardiac glycoside component of PBI-05204, can quantitatively account for regulation of BDNF at both the protein and transcriptional levels. Together, these findings support further investigation of cardiac glycosides in providing neuroprotection in the context of ischemic stroke. PMID:24431454

Van Kanegan, Michael J.; He, Dong Ning; Dunn, Denise E.; Yang, Peiying; Newman, Robert A.; West, Anne E.

2014-01-01

432

17-Hydroxygeranyllinalool glycosides are major resistance traits of Nicotiana obtusifolia against attack from tobacco hornworm larvae.  

PubMed

In the Great Basin Desert, Nicotiana obtusifolia (synonymous with Nicotiana trigonophylla) and Nicotiana attenuata co-occur, but the former is frequently less attacked by larvae of the tobacco hornworm than the latter, despite having lower nicotine and trypsin protease inhibitor defenses. Glycosides of the diterpene, 17-hydroxygeranyllinalool (HGL-DTGs) have recently been found to be important defenses of N. attenuata. Total HGL-DTG levels are 5-fold higher in N. obtusifolia than in N. attenuata, and we characterize the three major HGL-DTGs purified from N. obtusifolia leaves as: 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-17-hydroxygeranyllinalool-17-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside; nicotinoside III and its malonic acid conjugates. Using APCI- and ESI-LC-MS, we also identified mono- and diacetyl-nicotinoside III and quercetin glycosides. To evaluate the defensive value of these HGL-DTGs, we used virus-induced-gene silencing to reduce the transcript levels of geranylgeranyl diphosphate synthase and total HGL-DTG levels in both species. When fed on silenced plants, larvae gained up to about two times more mass than those that fed on empty vector control plants of both species. We conclude that HGL-DTGs function as the most important direct defenses for both N. attenuata and N. obtusifolia. PMID:20452633

Jassbi, Amir Reza; Zamanizadehnajari, Simin; Baldwin, Ian T

2010-07-01

433

Topical Anti-Inflammatory Effects of Isorhamnetin Glycosides Isolated from Opuntia ficus-indica.  

PubMed

Opuntia ficus-indica (OFI) has been widely used in Mexico as a food and for the treatment of different health disorders such as inflammation and skin aging. Its biological properties have been attributed to different phytochemicals such as the isorhamnetin glycosides which are the most abundant flavonoids. Moreover, these compounds are considered a chemotaxonomic characteristic of OFI species. The aim of this study was to evaluate the effect of OFI extract and its isorhamnetin glycosides on different inflammatory markers in vitro and in vivo. OFI extract was obtained by alkaline hydrolysis of OFI cladodes powder and pure compounds were obtained by preparative chromatography. Nitric oxide (NO), cyclooxygenase-2 (COX-2), tumor necrosis factor- (TNF-) ?, and interleukin- (IL-) 6 production were measured. NO production was tested in lipopolysaccharide-stimulated RAW 264.7 cells while in vivo studies were carried on croton oil-induced ear edema model. OFI extract and diglycoside isorhamnetin-glucosyl-rhamnoside (IGR) at 125?ng/mL suppressed the NO production in vitro (73.5 ± 4.8% and 68.7 ± 5.0%, resp.) without affecting cell viability. Likewise, IGR inhibited the ear edema (77.4 ± 5.7%) equating the indomethacin effects (69.5 ± 5.3%). Both IGR and OFI extract significantly inhibited the COX-2, TNF-?, and IL-6 production. IGR seems to be a suitable natural compound for development of new anti-inflammatory ingredient. PMID:25821823

Antunes-Ricardo, Marilena; Gutiérrez-Uribe, Janet A; Martínez-Vitela, Carlos; Serna-Saldívar, Sergio O

2015-01-01

434

Topical Anti-Inflammatory Effects of Isorhamnetin Glycosides Isolated from Opuntia ficus-indica  

PubMed Central

Opuntia ficus-indica (OFI) has been widely used in Mexico as a food and for the treatment of different health disorders such as inflammation and skin aging. Its biological properties have been attributed to different phytochemicals such as the isorhamnetin glycosides which are the most abundant flavonoids. Moreover, these compounds are considered a chemotaxonomic characteristic of OFI species. The aim of this study was to evaluate the effect of OFI extract and its isorhamnetin glycosides on different inflammatory markers in vitro and in vivo. OFI extract was obtained by alkaline hydrolysis of OFI cladodes powder and pure compounds were obtained by preparative chromatography. Nitric oxide (NO), cyclooxygenase-2 (COX-2), tumor necrosis factor- (TNF-) ?, and interleukin- (IL-) 6 production were measured. NO production was tested in lipopolysaccharide-stimulated RAW 264.7 cells while in vivo studies were carried on croton oil-induced ear edema model. OFI extract and diglycoside isorhamnetin-glucosyl-rhamnoside (IGR) at 125?ng/mL suppressed the NO production in vitro (73.5 ± 4.8% and 68.7 ± 5.0%, resp.) without affecting cell viability. Likewise, IGR inhibited the ear edema (77.4 ± 5.7%) equating the indomethacin effects (69.5 ± 5.3%). Both IGR and OFI extract significantly inhibited the COX-2, TNF-?, and IL-6 production. IGR seems to be a suitable natural compound for development of new anti-inflammatory ingredient.

Antunes-Ricardo, Marilena; Gutiérrez-Uribe, Janet A.; Martínez-Vitela, Carlos; Serna-Saldívar, Sergio O.

2015-01-01

435

Crystal structure and characterization of the glycoside hydrolase family 62 ?-L-arabinofuranosidase from Streptomyces coelicolor.  

PubMed

?-L-arabinofuranosidase, which belongs to the glycoside hydrolase family 62 (GH62), hydrolyzes arabinoxylan but not arabinan or arabinogalactan. The crystal structures of several ?-L-arabinofuranosidases have been determined, although the structures, catalytic mechanisms, and substrate specificities of GH62 enzymes remain unclear. To evaluate the substrate specificity of a GH62 enzyme, we determined the crystal structure of ?-L-arabinofuranosidase, which comprises a carbohydrate-binding module family 13 domain at its N terminus and a catalytic domain at its C terminus, from Streptomyces coelicolor. The catalytic domain was a five-bladed ?-propeller consisting of five radially oriented anti-parallel ?-sheets. Sugar complex structures with l-arabinose, xylotriose, and xylohexaose revealed five subsites in the catalytic cleft and an l-arabinose-binding pocket at the bottom of the cleft. The entire structure of this GH62 family enzyme was very similar to that of glycoside hydrolase 43 family enzymes, and the catalytically important acidic residues found in family 43 enzymes were conserved in GH62. Mutagenesis studies revealed that Asp(202) and Glu(361) were catalytic residues, and Trp(270), Tyr(461), and Asn(462) were involved in the substrate-binding site for discriminating the substrate structures. In particular, hydrogen bonding between Asn(462) and xylose at the nonreducing end subsite +2 was important for the higher activity of substituted arabinofuranosyl residues than that for terminal arabinofuranoses. PMID:24482228

Maehara, Tomoko; Fujimoto, Zui; Ichinose, Hitomi; Michikawa, Mari; Harazono, Koichi; Kaneko, Satoshi

2014-03-14

436

Biogenesis of C-Glycosyl Flavones and Profiling of Flavonoid Glycosides in Lotus (Nelumbo nucifera)  

PubMed Central

Flavonoids in nine tissues of Nelumbo nucifera Gaertner were identified and quantified by high-performance liquid chromatography with diode array detector (HPLC-DAD) and HPLC-electrospray ionization-mass spectrometry (HPLC-ESI-MSn). Thirty-eight flavonoids were identified; eleven C-glycosides and five O-glycosides were discovered for the first time in N. nucifera. Most importantly, the C-glycosyl apigenin or luteolin detected in lotus plumules proved valuable for deep elucidation of flavonoid composition in lotus tissues and for further utilization as functional tea and medicine materials. Lotus leaves possessed the significantly highest amount of flavonoids (2.06E3±0.08 mg 100 g?1 FW) and separating and purifying the bioactive compound, quercetin 3-O-glucuronide, from leaves showed great potential. In contrast, flavonoids in flower stalks, seed coats and kernels were extremely low. Simultaneously, the optimal picking time was confirmed by comparing the compound contents in five developmental phases. Finally, we proposed the putative flavonoid biosynthesis pathway in N. nucifera. PMID:25279809

Li, Shan-Shan; Wu, Jie; Chen, Li-Guang; Du, Hui; Xu, Yan-Jun; Wang, Li-Jing; Zhang, Hui-Jin; Zheng, Xu-Chen; Wang, Liang-Sheng

2014-01-01

437

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

438

Fast methodology of analysing major steviol glycosides from Stevia rebaudiana leaves.  

PubMed

The aim of this work is to propose an HPLC method for analysing major steviol glycosides as well as to optimise the extraction and clarification conditions for obtaining these compounds. Toward this aim, standards of stevioside and rebaudioside A with purities ?99.0%, commercial samples from different companies and Stevia rebaudiana Bertoni leaves from Paraguay supplied by Insobol, S.L., were used. The analytical method proposed is adequate in terms of selectivity, sensitivity and accuracy. Optimum extraction conditions and adequate clarification conditions have been set. Moreover, this methodology is safe and eco-friendly, as we use only water for extraction and do not use solid-phase extraction, which requires solvents that are banned in the food industry to condition the cartridge and elute the steviol glycosides. In addition, this methodology consumes little time as leaves are not ground and the filtration is faster, and the peak resolution is better as we used an HPLC method with gradient elution. PMID:24679813

Lorenzo, Cándida; Serrano-Díaz, Jéssica; Plaza, Miguel; Quintanilla, Carmen; Alonso, Gonzalo L

2014-08-15

439

Phenylethanoid glycosides from Digitalis purpurea and Penstemon linarioides with PKCalpha-inhibitory activity.  

PubMed

In a continuation of our search for potential tumor inhibitors from plants, it was found that the CH2Cl2-MeOH (1:1) extracts from Digitalis purpurea and Penstemon linarioides both showed PKCalpha-inhibitory bioactivity. Bioassay-directed fractionation of the extract from D. purpurea yielded the new, weakly active phenylethanoid glycoside 2-(3-hydroxy-4-methoxy-phenyl)-ethyl-O-(alpha-L-rhamnosyl)-(1-->3) -O- (alpha-L-rhamnosyl)-(1-->6)-4-O-E-feruloyl-beta-D-glucopy ran oside (1) together with the four known compounds calceolarioside A (2), calceolarioside B (3), forsythiaside (4), and plantainoside D (5). The extract from P. linarioides yielded the three known glycosides leucosceptoside A (6), acteoside (7), and poliumoside (8), together with the iridoid plantarenaloside (9). All of the isolated compounds, except compound 9, showed inhibitory activity against PKCalpha with IC50 values (in microM) of 125 (1), 0.6 (2), 4.6 (3), 1.9 (4), 14.8 (5), 19.0 (6), 9.3 (7), and 24.4 (8). PMID:9834166

Zhou, B N; Bahler, B D; Hofmann, G A; Mattern, M R; Johnson, R K; Kingston, D G

1998-11-01

440

Two new acyclic diterpene glycosides from fruits of Habanero, Capsicum chinense.  

PubMed

Four acyclic diterpene glycosides were extracted from Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence. Two of these glycosides were identified as capsianoside XIII and capsianoside XV. The other two were new ones and were characterized as 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 17,19-dihydroxy-6E,10E,14Z-(3S)-geranyllinalool 17-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside and 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 6E,10E,14Z-(3S)-17-hydroxy-geranyllinalool 17-O-[3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 6'E,10'E,14'Z-(3'S)-13'R,19'-dihydroxy-geranyllinalool-16'-oyl (16'-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside. PMID:19571420

Lee, Jong-Hyun; El-Aasr, Mona; Ikeda, Tsuyoshi; Oda, Kana; Miyashita, Hiroyuki; Yoshimitsu, Hitoshi; Okawa, Masafumi; Kinjo, Junei; Nohara, Toshihiro

2009-07-01

441

Differential Recognition and Hydrolysis of Host Carbohydrate Antigens by Streptococcus pneumoniae Family 98 Glycoside Hydrolases  

SciTech Connect

The presence of a fucose utilization operon in the Streptococcus pneumoniae genome and its established importance in virulence indicates a reliance of this bacterium on the harvesting of host fucose-containing glycans. The identities of these glycans, however, and how they are harvested is presently unknown. The biochemical and high resolution x-ray crystallographic analysis of two family 98 glycoside hydrolases (GH98s) from distinctive forms of the fucose utilization operon that originate from different S. pneumoniae strains reveal that one enzyme, the predominant type among pneumococcal isolates, has a unique endo-{beta}-galactosidase activity on the LewisY antigen. Altered active site topography in the other species of GH98 enzyme tune its endo-{beta}-galactosidase activity to the blood group A and B antigens. Despite their different specificities, these enzymes, and by extension all family 98 glycoside hydrolases, use an inverting catalytic mechanism. Many bacterial and viral pathogens exploit host carbohydrate antigens for adherence as a precursor to colonization or infection. However, this is the first evidence of bacterial endoglycosidase enzymes that are known to play a role in virulence and are specific for distinct host carbohydrate antigens. The strain-specific distribution of two distinct types of GH98 enzymes further suggests that S. pneumoniae strains may specialize to exploit host-specific antigens that vary from host to host, a factor that may feature in whether a strain is capable of colonizing a host or establishing an invasive infection.

Higgins, M.; Whitworth, G; El Warry, N; Randriantsoa, M; Samain, E; Burke, R; Vocadlo, D; Boraston, A

2009-01-01

442

Influence of drying method on steviol glycosides and antioxidants in Stevia rebaudiana leaves.  

PubMed

The application of different drying conditions (hot air drying at 100 °C and 180 °C, freeze drying and shade drying) on steviol glycosides (stevioside, dulcoside A, rebaudioside A and rebaudioside C) and antioxidants in Stevia leaves was evaluated. Stevioside, the major glycoside found in fresh leaves (81.2mg/g), suffered an important reduction in all cases, although shade drying was the least aggressive treatment. Considering the antioxidant parameters (total phenols, flavonoids and total antioxidants), the most suitable drying method was hot air at 180 °C, since it substantially increased all of them (76.8 mg gallic acid, 45.1mg catechin and 126 mg Trolox, all equivalent/g Stevia, respectively), with respect to those present in fresh leaves (44.4, 2.5 and 52.9 mg equivalent/g). Therefore, the ideal method for drying Stevia leaves depends on their final use (sweetener or antioxidant), although, hot air at 180 °C is the most recommendable if only one treatment has to be chosen. PMID:25442516

Periche, Angela; Castelló, María Luisa; Heredia, Ana; Escriche, Isabel

2015-04-01

443

New cardenolide glycosides from the seeds of Digitalis purpurea and their cytotoxic activity.  

PubMed

A chemical investigation of Digitalis purpurea seeds led to the isolation of three new cardenolide glycosides (1, 8 and 11), together with 12 known cardenolide glycosides (2-7, 9, 10 and 12-15). The structures of 1, 8 and 11 were determined by 1D and 2D NMR spectroscopic analyses and the results of an acid or enzymatic hydrolysis. The cytotoxic activity of the isolated compounds (1-15) against HL-60 leukemia cells was examined. Compounds 2, 9, 11 and 12 showed potent cytotoxicity against HL-60 cells with respective 50% inhibition concentration (IC50) values of 0.060, 0.069, 0.038, and 0.034 µM. Compounds 2, 9 and 11 also exhibited potent cytotoxic activity against HepG2 human liver cancer cells with respective IC50 values of 0.38, 0.79, and 0.71 µM. An investigation of the structure-activity relationship showed that the cytotoxic activity was reduced by the introduction of a hydroxy group at C-16 of the digitoxigenin aglycone, methylation of the C-3' hydroxy group at the fucopyranosyl moiety, and acetylation of the C-3' hydroxy group at the digitoxopyranoyl moiety. PMID:23748755

Kuroda, Minpei; Kubo, Satoshi; Matsuo, Yukiko; Atou, Tomomi; Satoh, Junichi; Fujino, Tomofumi; Hayakawa, Makio; Mimaki, Yoshihiro

2013-01-01

444

Iridoid glycoside sequestration byThessalia leanira (Lepidoptera: Nymphalidae) feeding onCastilleja integra (Scrophulariaceae).  

PubMed

A small population of a polyvoltine checkerspot butterfly,Thessalia leanira fulvia (also known asChlosyne leanira ssp.fulvia), was found to useCastilleja integra as a larval food plant at a localized site (Burnt Mill) southwest of Pueblo, Colorado. Field-captured adult butterflies contained the major iridoid glycosides (catalpol and macfadienoside) of theCastilleja. The content of a third iridoid glycoside, methyl shanzhiside, was also relatively high in the collected butterflies even though most individualCastilleja plants at Burnt Mill contained little or no methyl shanzhiside. Only a few plants, restricted to a small area, did contain appreciable methyl shanzhiside. Most of the plants that lacked the ester methyl shanzhiside contained shanzhiside, the corresponding free carboxylic acid.Thessalia larvae did not normally methylate the acid to produce methyl shanzhiside. Larvae that stopped feeding at an early instar, but yet survived several weeks, did contain major amounts of methyl shanzhiside. It is suggested that only larvae that overwinter or otherwise enter diapause convert shanzhiside to methyl shanzhiside. TheCastilleja food plant also contained iridoids other than catalpol and macfadienoside, sometimes in major amounts, but these were never found in larvae, pupae, or butterflies. PMID:24249134

Mead, E W; Foderaro, T A; Gardner, D R; Stermitz, F R

1993-06-01

445

Time reversing solitary waves.  

PubMed

We present new results for the time reversal of nonlinear pulses traveling in a random medium, in particular for solitary waves. We consider long water waves propagating in the presence of a spatially random depth. Both hyperbolic and dispersive regimes are considered. We demonstrate that in the presence of properly scaled stochastic forcing the solution to the nonlinear (shallow water) conservation law is regularized leading to a viscous shock profile. This enables time-reversal experiments beyond the critical time for shock formation. Furthermore, we present numerical experiments for the time-reversed refocusing of solitary waves in a regime where theory is not yet available. Solitary wave refocusing simulations are performed with a new Boussinesq model, both in transmission and in reflection. PMID:15089472

Fouque, Jean-Pierre; Garnier, Josselin; Muñoz Grajales, Juan Carlos; Nachbin, André

2004-03-01

446

Glucose reversion reaction kinetics.  

PubMed

The reversion reactions of glucose in mildly acidic aqueous solutions have been studied, and the kinetics of conversion to disaccharides has been modeled. The experiments demonstrate that, at high sugar loadings, up to 12 wt % of the glucose can be converted into reversion products. The reversion products observed are primarily disaccharides; no larger oligosaccharides were observed. Only disaccharides linked to the C1 carbon of one of the glucose residues were observed. The formation of 1,6-linked disaccharides was favored, and alpha-linked disaccharides were formed at higher concentrations than beta-linked disaccharides. This observation can be rationalized on the basis of steric effects. At temperatures >140 degrees C, the disaccharides reach equilibrium with glucose and the reversion reaction competes with dehydration reactions to form 5-hydroxymethylfurfural. As a result, disaccharide formation reaches a maximum at reaction times <10 min and decreases with time. At temperatures <130 degrees C, disaccharide formation reaches a maximum at reaction times >30 min. As expected, disaccharide formation exhibits a second-order dependence upon glucose concentration. Levoglucosan formation is also observed; because it shows a first-order dependence upon glucose concentration, its formation is more significant at low concentrations (10 mg mL(-1)), whereas disaccharide formation dominates at high concentrations (200 mg mL(-1)). Experiments conducted using glucose and its disaccharides were calibrated with readily available standards. The kinetic parameters for hydrolysis of some glucodisaccharides could be compared to published literature values. From these experiments, the kinetics and activation energies for the reversion reactions have been calculated. The rate parameters can be used to model the formation of the disaccharides as a function of reaction time and temperature. A new and detailed picture of the molecular mechanism of these industrially important reversion reactions has been developed. PMID:20429509

Pilath, Heidi M; Nimlos, Mark R; Mittal, Ashutosh; Himmel, Michael E; Johnson, David K

2010-05-26

447

Cyanuric Chloride as an Efficient Catalyst for the Synthesis of 2,3-Unsaturated O-Glycosides by Ferrier Rearrangement  

PubMed Central

Cyanuric chloride has been found to be an efficient catalyst for the synthesis of 2,3-unsaturated O-glycosides from the reaction of 3,4,6-tri-O-acetyl-D-glucal and a wide range of alcohols in dichloromethane at room temperature. The experimental procedure is simple, and the products are obtained in high yields. PMID:24574881

Yang, Xiaojuan; Li, Na

2014-01-01

448

Validation of HPLC-UV method for determination of minor glycosides contained in Stevia rebaudiana Bertoni leaves.  

PubMed

Leaves of Stevia rebaudiana contain glycosides with sweetness and biological activity. However besides the major glycosides, there are other glycosides within extracts that may contribute to its activity, and therefore it is important to quantify them. In this work, an isocratic HPLC method was validated for determination of dulcoside A, steviolbioside, rebaudioside C and rebaudioside B. An HPLC method was performed using a C18 column (250?×?4.6?mm, particle size 5?µm) and a UV detector set at 210?nm. The mobile phase consisted of a 32:68 (v/v) mixture of acetonitrile and sodium phosphate buffer (10?mmol/L, pH?2.6), set to a flow rate of 1.0?mL/min. The calculated parameters were: sensitivity, linearity, limit of detection (LOD), limit of quantification (LOQ), accuracy and precision. The calibration curves were linear over the working range 25-150?µg/mL, with coefficient of correlation of ?0.99 and coefficient of determination of ?0.98. The LOD was 5.68-8.81?µg/mL, while the LOQ was 17.21-26.69?µg/mL. The percentage recoveries of fortified samples were 100?±?10% and precision, relative standard deviation, was <10%. The method validation showed accuracy, linearity and precision; therefore this method can be applied for quantitative analysis of minor steviol glycosides in S. rebaudiana leaves. Copyright © 2014 John Wiley & Sons, Ltd. PMID:25296637

Aranda-González, Irma; Moguel-Ordoñez, Yolanda; Betancur-Ancona, David

2015-05-01

449

Evaluation of anti-HIV-1 activity of a new iridoid glycoside isolated from Avicenna marina, in vitro.  

PubMed

This study was carried out to check the efficacy of methanol seed extract of Avicenna marina and its column chromatographic fractions on Peripheral Blood Mono nuclear Cells (PBMCs) toxicity and HIV-1 replication. The anti-HIV-1 activities of crude methanol extract and its fractions were performed by use of real-time polymerase chain reaction (PCR) assay and HIV-1 p24 antigen kit. A time of drug addiction approach was also done to identify target of anti-HIV compound. The activity of the extracts on CD4, CD3, CD19 and CD45 expression in lymphocytes population was performed by use of flow cytometry. The most active anti-HIV agent was detected by spectroscopic analysis as 2'-O-(4-methoxycinnamoyl) mussaenosidic acid. The apparent effective concentrations for 50% virus replication (EC50) of methanol extract and iridoid glycoside were 45 and 0.1 ?g/ml respectively. The iridoid glycoside also did not have any observable effect on the proportion of CD4, CD3, CD19 and CD45 cells or on the intensity of their expressions on PBMCs. In addition, the expression level of C-C chemokine receptor type 5 (CCR5) and chemokine receptor type 4 (CXCR4) on CD4(+) T cells were decreased in cells treated with this iridoid glycoside. The reduction of these two HIV coreceptors and the result of time of addition study demonstrated that this iridoid glycoside restricts HIV-1 replication on the early stage of HIV infection. PMID:25239814

Behbahani, Mandana

2014-11-01

450

Re-evaluating the role of ascorbic acid and phenolic glycosides in ozone scavenging in the leaf apoplast of  

E-print Network

Re-evaluating the role of ascorbic acid and phenolic glycosides in ozone scavenging in the leaf that O3 scavenging by direct reactions with reduced AA was very limited. In regard to phenolics, O3 of sinapoyl malate. However, modelling of O3 scavenging in the apoplast indicated that sinapoyl malate

Jones, Alan M.

451

Determination of flavonol glycosides in green tea, oolong tea and black tea by UHPLC compared to HPLC.  

PubMed

An UHPLC method for the determination of flavonol glycosides (FOG) from green and oolong tea vs. black tea has been developed for the first time. Sample clean-up method by means of polyamide column chromatography was optimized with multiple-step elution. Using UHPLC and HPLC with gradient elution and photodiode array detection, eighteen FOG compounds were determined with the aid of electrospray tandem mass spectrometry. These FOG compounds were qualified on both UHPLC and HPLC, and this UHPLC method successfully separated rutin (quercetin-3-O-rutinoside) and K-grg (kaempferol-3-O-glucorhamnoglucoside) while conventional HPLC method did not. The total amounts of FOG compounds in the tea samples were 2.32-5.67g/kg dry weight (calculated as aglycones), and there is no significant difference for the total FOG content among green tea, oolong tea and black tea. However, kaempferol glycosides are more abundant in green teas, while oolong tea has more quercetin and myricetin glycosides. In black tea quercetin glycosides were most abundant. PMID:25863606

Jiang, Heyuan; Engelhardt, Ulrich H; Thräne, Claudia; Maiwald, Beate; Stark, Janina

2015-09-15

452

Cardiac glycosides provide neuroprotection against ischemic stroke: Discovery by a brain slice-based compound screening platform  

PubMed Central

We report here the results of a chemical genetic screen using small molecules with known pharmacologies coupled with a cortical brain slice-based model for ischemic stroke. We identified a small-molecule compound not previously appreciated to have neuroprotective action in ischemic stroke, the cardiac glycoside neriifolin, and demonstrated that its properties in the brain slice assay included delayed therapeutic potential exceeding 6 h. Neriifolin is structurally related to the digitalis class of cardiac glycosides, and its putative target is the Na+/K+-ATPase. Other cardiac glycoside compounds tested also showed neuroprotective activity, although with lower apparent potencies. In subsequent whole-animal studies, we found that neriifolin provided significant neuroprotection in a neonatal model of hypoxia/ischemia and in a middle cerebral artery occlusion model of transient focal ischemia. The neuroprotective potential of Na+/K+-ATPase is of particular interest because of its known “druggability”; indeed, Food and Drug Administration-approved, small-molecule compounds such as digitoxin and digoxin have been in clinical usage for congestive heart failure and arrhythmias for several decades. Thus, an existing cardiac glycoside or closely related compound could provide an accelerated path toward clinical trial testing for ischemic stroke. Our findings underscore the important role that hypothesis-neutral, high-content, tissue-based screens can play in the identification of new candidate drugs and drug targets for the treatment of diseases for which validated therapeutic pathways are not currently available. PMID:16793926

Wang, James K. T.; Portbury, Stuart; Thomas, Mary Beth; Barney, Shawn; Ricca, Daniel J.; Morris, Dexter L.; Warner, David S.; Lo, Donald C.

2006-01-01

453

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

454

Direct analysis of steviol glycosides from Stevia leaves by ambient ionization mass spectrometry performed on whole leaves.  

PubMed

Leaf spray mass spectrometry is explored as a fast and simple way for direct analysis of sweet glycosides in fresh untreated Stevia leaves without sample pretreatment. In this technique, a fresh triangular piece of Stevia leaf serves as both sample and substrate. Application of a butanol : methanol : water mixture and a high voltage to intact leaf material produces a high electric field at the tip of the leaf. This results in field emission of charged droplets containing the glycosides. The resulting dry ions are detected by mass spectrometry and confirmed by tandem mass spectrometry and exact mass measurements. A comparison between leaf spray and other ambient ionization methods which are successful for screening glycosides in Stevia leaves--desorption electrospray ionization, low temperature plasma and paper spray--shows that leaf spray produces the highest quality spectra. It is also extremely easy to implement with no need for nebulizing gas or sample preparation and is suited to semi-quantitative determinations. The potential for the application of leaf spray mass spectrometry to direct and rapid screening of plant materials is here realized in the case of Stevia sweet glycosides. PMID:22606683

Zhang, J Isabella; Li, Xin; Ouyang, Zheng; Cooks, R Graham

2012-07-01

455

Differential toxicity of a phenolic glycoside from quaking aspen to Papilio glaucus butterfly subspecies, hybrids and backcrosses  

Microsoft Academic Search

Papilio glaucus subspecies, hybrids and backcrosses exhibit greatly different abilities to use quaking aspen (Populus tremuloides) and other members of the Salicaceae as host plants. This study was conducted to test the hypotheses that phenolic glycosides account for the differences in larval performance, and that differential performance is correlated with differential larval esterase activities. To test the hypotheses we conducted

J. Mark Scriber; Richard L. Lindroth; James Nitao

1989-01-01

456

Acaricidal effects of cardiac glycosides, azadirachtin and neem oil against the camel tick, Hyalomma dromedarii (Acari: Ixodidae).  

PubMed

The cardiac glycoside, digitoxin, from Digitalis purpurea L (Scrophulariaceae), a cardiac glycosidal (cardenolide) extract from Calotropis procera (Ait) R Br (Asclepiadaceae), azadirachtin and neem oil from Azadirachta indica A Juss (Meliaceae) were tested for their effects against larvae and adult stages of the camel tick, Hyalomma dromedarii Koch (Acari: Ixodidae). The contact LC50 values of the first three materials against adults were 4.08, 9.63 and >40.7 microg cm(-2), respectively, whereas the dipping LC50 values of the four materials were 409.9, 1096, >5000 and >5000 mg litre(-1), respectively. Contact and dipping LC50 values of the extract and azadirachtin against larvae were 6.16, >20.3 microg cm(-2) and 587.7 and >2500 mg litre(-1), respectively. Azadirachtin had no effects on egg production or feeding of adults up to 5000 mg litre(-1); however at 2500 mg litre(-1), it caused significant reduction in feeding activity of larve, prolonged the period for moulting to nymphal stage, and caused 60% reduction in moultability. Results of the two cardiac glycoside materials are comparable with those of several commercial acaricides. The risks and benefits associated with the use of cardiac glycosides are considered. PMID:14620053

Al-Rajhy, DiefAlla H; Alahmed, Azzam M; Hussein, Hamdy I; Kheir, Salah M

2003-11-01

457

Unlike Quercetin Glycosides, Cyanidin Glycoside in Red Leaf Lettuce Responds More Sensitively to Increasing Low Radiation Intensity before than after Head Formation Has Started  

PubMed Central

This study investigated the effect of low-level photosynthetic photon flux density (PPFD; 43–230 ?mol m–2 s–1) on the major phenolic compounds of red leaf lettuce in three growth stages, before, during, and after head formation, using HPLC-DAD-ESI-MS2 and evaluating via multiple regression analysis. Generally, the light-related increase of flavonoid glycosides was structure and growth stage-dependent. In detail, an interaction was detected between plant age and PPFD regarding cyanidin-3-O-(6?-O-malonyl)-glucoside concentration: the increase was strongest before head formation. The relationship between PPFD and quercetin-3-O-(6?-O-malonyl)-glucoside concentration was linear, whereas the increase of quercetin-3-O-glucoside and -3-O-glucuronide concentrations abated with increasing PPFD. Independent of growth stage, the caffeic acid derivatives concentration was not related to PPFD. All major phenolic compounds decreased with plant age. These results show the differential regulation of cyanidin, quercetin, and caffeic acid derivatives in lettuce, although closely connected biosynthetically, and emphasize the importance of ontogeny in the study of plant physiology. PMID:24382136

2014-01-01

458

Unlike quercetin glycosides, cyanidin glycoside in red leaf lettuce responds more sensitively to increasing low radiation intensity before than after head formation has started.  

PubMed

This study investigated the effect of low-level photosynthetic photon flux density (PPFD; 43-230 ?mol m(-2) s(-1)) on the major phenolic compounds of red leaf lettuce in three growth stages, before, during, and after head formation, using HPLC-DAD-ESI-MS(2) and evaluating via multiple regression analysis. Generally, the light-related increase of flavonoid glycosides was structure and growth stage-dependent. In detail, an interaction was detected between plant age and PPFD regarding cyanidin-3-O-(6"-O-malonyl)-glucoside concentration: the increase was strongest before head formation. The relationship between PPFD and quercetin-3-O-(6"-O-malonyl)-glucoside concentration was linear, whereas the increase of quercetin-3-O-glucoside and -3-O-glucuronide concentrations abated with increasing PPFD. Independent of growth stage, the caffeic acid derivatives concentration was not related to PPFD. All major phenolic compounds decreased with plant age. These results show the differential regulation of cyanidin, quercetin, and caffeic acid derivatives in lettuce, although closely connected biosynthetically, and emphasize the importance of ontogeny in the study of plant physiology. PMID:24382136

Becker, Christine; Klaering, Hans-Peter; Schreiner, Monika; Kroh, Lothar W; Krumbein, Angelika

2014-07-23

459

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

460

Reversible data hiding  

Microsoft Academic Search

We present a novel reversible (lossless) data hiding (embedding) technique, which enables the exact recovery of the original host signal upon extraction of the embedded information. A general- ization of the well-known LSB (least significant bit) modification is proposed as the data embedding method, which introduces addi- tional operating points on the capacity-distortion curve. Lossless recovery of the original is

Mehmet Utku Celik; Gaurav Sharmab; Eli Saber; A. Murat Tekalp

2002-01-01

461

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

462

Expression pattern of glycoside hydrolase genes in Lutzomyia longipalpis reveals key enzymes involved in larval digestion  

PubMed Central

The sand fly Lutzomyia longipalpis is the most important vector of American Visceral Leishmaniasis. Adults are phytophagous (males and females) or blood feeders (females only), and larvae feed on solid detritus. Digestion in sand fly larvae has scarcely been studied, but some glycosidase activities putatively involved in microorganism digestion were already described. Nevertheless, the molecular nature of these enzymes, as the corresponding genes and transcripts, were not explored yet. Catabolism of microbial carbohydrates in insects generally involves ?-1,3-glucanases, chitinases, and digestive lysozymes. In this work, the transcripts of digestive ?-1,3-glucanase and chitinases were identified in the L. longipalpis larvae throughout analysis of sequences and expression patterns of glycoside hydrolases families 16, 18, and 22. The activity of one i-type lysozyme was also registered. Interestingly, this lysozyme seems to play a role in immunity, rather than digestion. This is the first attempt to identify the molecular nature of sand fly larval digestive enzymes. PMID:25140153

Moraes, Caroline da Silva; Diaz-Albiter, Hector M.; Faria, Maiara do Valle; Sant'Anna, Maurício R. V.; Dillon, Rod J.; Genta, Fernando A.

2014-01-01

463

Potent airway smooth muscle relaxant effect of cynatratoside B, a steroidal glycoside isolated from Cynanchum stauntonii.  

PubMed

The dried roots of Cynanchum stauntonii in having cough-relieving efficacy are commonly included in traditional antitussive formulas. The active components in a C. stauntonii root extract responsible for airway relaxation were isolated using an ex vivo bioassay-guided fractionation method, in which subfractions were evaluated for their inhibitory effects on the contraction of isolated rat tracheal rings by isometric tension measurements. A steroidal glycoside, cynatratoside B (1), identified by LC-MS and NMR spectroscopic analysis, was shown to have potent inhibition on acetylcholine- and carbachol-induced tracheal contractions. The present data provide scientific evidence to support the traditional use of C. stauntonii as an antitussive herbal medicine. PMID:24761833

Yue, Grace Gar-Lee; Chan, Kar-Man; To, Ming-Ho; Cheng, Ling; Fung, Kwok-Pui; Leung, Ping-Chung; Lau, Clara Bik-San

2014-04-25

464

New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects.  

PubMed

A new chalcanonol glycoside dimer, bis-O-[(I-4') ? (II-6')]-?-hydroxyphloretin-2'-O-?-glucoside (1), in addition to six known compounds, namely ( - )-epicatechin (2) and ( - )-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), ?-sitosterol (7) and ?-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2'-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers. PMID:25230777

Abdel Bar, Fatma M

2014-09-18

465

Characterisation of free and glycosidically bound aroma compounds of La Mancha Verdejo white wines.  

PubMed

The aroma of Verdejo La Mancha white wines was studied by instrumental and sensory analysis across five consecutive vintages to determine their typicity and quality. Free and glycosidically-bound aroma compounds were isolated by solid phase extraction (SPE) to later be analysed using gas chromatography-mass spectrometry (GC/MS). Seventy-four (74) free aroma compounds and thirty-six (36) bound aroma compounds were identified and quantified in La Mancha Verdejo wines oven this five year period. Based on the result, Verdejo white wines presents a complex chemical profile with a wealth of aromas in its aromatic composition. The sensory profile of Verdejo wines was evaluated by experienced wine-tasters and was characterised by fresh, citric, green apple, fruity and tropical fruit aroma descriptors. This study shows the first complete aromatic characterisation of La Mancha Verdejo white wines, also the data suggest that these wines present a great aromatic potential. PMID:25466143

Sánchez-Palomo, E; Alonso-Villegas, R; González Viñas, M A

2015-04-15

466

Immunopotentiation of Caffeoyl Glycoside from Picrorhiza scrophulariiflora on activation and cytokines secretion of immunocyte in vitro.  

PubMed

Many natural products have been used as immunomodulators either as immunosuppressants or immunostimulators. Recently, our lab has successfully isolated a 1,6-di-O-caffeoyl-beta-D-glucopyranoside, monomer named Caffeoyl Glycoside (CG) from the roots of Picrorhiza scrophulariiflora (Kutki). In the present study, we evaluated the effects of this compound on immunomodulation in vitro. Our results showed that CG stimulated cell proliferation of splenocytes and peritoneal macrophages, and enhanced the cytotoxicity of natural killer (NK) cells significantly. CG also increased CD4 and CD8 cell populations. Moreover, we found that CG has immunomodulatory activity by regulating expression of Th1 and Th2 related cytokines. Taken together, these results indicated that CG might have potential effects in regulating the immune system, and this compound might be a useful immunotherapeutic agent in treating various immunity-related diseases. PMID:18721903

Zeng, Sheng; Wang, Dacheng; Cao, Yongguo; An, Na; Zeng, Fanqin; Han, Chuntian; Song, Yu; Deng, Xuming

2008-12-10

467

Identification and quantification of glycoside flavonoids in the energy crop Albizia julibrissin.  

PubMed

Oxygen radical absorbance capacity (ORAC) values showed that methanolic extracts of Albizia julibrissin foliage displayed antioxidant activity. High performance liquid chromatography (HPLC) and mass spectrometry (MS) techniques were utilized in the identification of the compounds. The analysis confirmed the presence of three compounds in A. julibrissin foliage methanolic extract: an unknown quercetin derivative with mass of 610 Da, hyperoside (quercetin-3-O-galactoside), and quercitrin (quercetin-3-O-rhamnoside). Fast performance liquid chromatography (FPLC) was employed to fractionate the crude A. julibrissin foliage methanolic extract into its individual flavonoid components. The flavonoids were quantified in terms of mass and their respective contribution to the overall ORAC value. Quercetin glycosides accounted for 2.0% of total foliage. PMID:16481160

Lau, Ching S; Carrier, Danielle J; Beitle, Robert R; Bransby, David I; Howard, Luke R; Lay, Jackson O; Liyanage, Rohana; Clausen, Edgar C

2007-01-01

468

Improvement of corn stover bioconversion efficiency by using plant glycoside hydrolase.  

PubMed

Plant cell wall is the most abundant substrate for bioethanol production, and plants also represent a key resource for glycoside hydrolase (GH). To exploit efficient way for bioethanol production with lower cellulase loading, the potential of plant GH for lignocellulose bioconversion was evaluated. The GH activity for cell wall proteins (CWPs) was detected from fresh corn stover (FCS), and the synergism of which with Trichoderma reesei cellulase was also observed. The properties for the GH of FCS make it a promising enzyme additive for lignocellulose biodegradation. To make use of the plant GH, novel technology for hydrolysis and ethanol fermentation was developed with corn stover as substrate. Taking steam-exploded corn stover as substrate for hydrolysis and ethanol fermentation, compared with T. reesei cellulase loaded alone, the final glucose and ethanol accumulation increased by 60% and 63% respectively with GH of FCS as an addition. PMID:21300542

Han, Yejun; Chen, Hongzhang

2011-04-01

469

Anomeric configuration, glycosidic linkage, and the solution conformational entropy of O-linked disaccharides.  

PubMed

Oligosaccharides perform a large number of biological roles, as dictated by their chemical structure and spatial arrangement. While conformational entropies are usually determined in vacuo by computer modeling, molecular recognition processes normally take place in solution. Here I show results of experiments using size-exclusion chromatography (SEC), an entropically driven solution technique. These clearly differentiate the individual contributions of the alpha and beta anomeric configurations and of the (1 --> 4) and (1 --> 6) glycosidic linkages to the solution conformational entropy of O-linked disaccharides. I also distinguish between the members of the ep