Sample records for peony glycosides reverses

  1. Peony glycosides produce antidepressant-like action in mice exposed to chronic unpredictable mild stress: Effects on hypothalamic-pituitary-adrenal function and brain-derived neurotrophic factor

    Microsoft Academic Search

    Qing-Qiu Mao; Siu-Po Ip; Kam-Ming Ko; Sam-Hip Tsai; Chun-Tao Che

    2009-01-01

    The root part of Paeonia lactiflora Pall. (Ranunculaceae), commonly known as peony, is a commonly used Chinese herb for the treatment of depression-like disorders. Previous studies in our laboratory have demonstrated that total glycosides of peony (TGP) produced antidepressant-like action in various mouse models of behavioral despair. The present study aimed to examine whether TGP could affect the chronic unpredictable

  2. EXTRACTION OF RHODIOLA ROSEA L. GLYCOSIDES BY REVERSED-PHASE CHROMATOGRAPHY. SALIDROZIDE COUNTER SYNTHESIS

    Microsoft Academic Search

    Sergey A. Patov; Iliya G. Zahozhy; Vasily V. Punegov; Alexander V. Kuchin; Michael I. Kodess

    Using low pressure column chromatography on sorbent Diasorb 130-?16?, the native glycosides from species Rhodiola rosea rhizomes (II, IV) have been isolated for the purpose of calibrating the analytical instrumentation. Their structure has been established by NMR spectrometry. A partial counter synthesis of salidroside (IV) has been carried out with Kennigs-Knorr method.

  3. 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...

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

    PubMed

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

    2015-04-01

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

  5. Antifungal active triterpene glycosides from sea cucumber Holothuria scabra

    Microsoft Academic Search

    HAN Hua; YI Yang-hua; LI Ling; LIU Bao-shu; LA Ming-ping; ZHANG Hong-wei

    To study the new antifungal active triterpene glycosides of sea cucumber Holothuria scabra. Triterpene glycosides from Holothuria scabra were separated and purified by silica gel chromatography, reversed-phase silica ge1 chromatography and RP-HPLC. Their structures were elucidated on the basis of spectral data and chemical evidence. Three triterpene glycosides were identified as scabraside A (1), echinoside A ( 2) and holothurin

  6. 75 FR 65648 - Notice of Proposed Withdrawal Extension and Opportunity for Public Meeting for the Peony, Pole...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-10-26

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

  7. Antifungal active triterpene glycosides from sea cucumber Holothuria scabra.

    PubMed

    Han, Hua; Yi, Yang-Hua; Li, Ling; Liu, Bao-Shu; La, Ming-Ping; Zhang, Hong-Wei

    2009-06-01

    To study the new antifungal active triterpene glycosides of sea cucumber Holothuria scabra. Triterpene glycosides from Holothuria scabra were separated and purified by silica gel chromatography, reversed-phase silica gel chromatography and RP-HPLC. Their structures were elucidated on the basis of spectral data and chemical evidence. Three triterpene glycosides were identified as scabraside A (1), echinoidea A (2) and holothurin A1 (3). Scabraside A (1) is a new triterpene glycoside, and compounds 2 and 3 were isolated from Holothuria scabra for the first time. They showed antifungal activities (1 < or = MIC80 < or = 16 microg mL(-1)). PMID:19806893

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

    PubMed

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

    2014-06-15

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

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

    NASA Astrophysics Data System (ADS)

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

    2015-07-01

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

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

    PubMed Central

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

    2012-01-01

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

  11. Molecular Characterization of Tree Peony Germplasm Using Sequence-Related Amplified Polymorphism Markers

    Microsoft Academic Search

    Xiao Yan Han; Liang Sheng Wang; Qing Yan Shu; Zheng An Liu; Su Xia Xu; Takuya Tetsumura

    2008-01-01

    This study examined 63 tree peony specimens, consisting of 3 wild species and 63 cultivars, using sequence-related amplified\\u000a polymorphism (SRAP) markers for the purpose of detecting genomic polymorphisms. Bulk DNA samples from each specimen were evaluated\\u000a with 23 SRAP primer pairs. Among the 296 different amplicons, 262 were polymorphic. The maximum parsimony, neighbor-joining,\\u000a and unweighted pair-group method using arithmetic average

  12. Two EST-derived marker systems for cultivar identification in tree peony.

    PubMed

    Zhang, J J; Shu, Q Y; Liu, Z A; Ren, H X; Wang, L S; De Keyser, E

    2012-02-01

    Tree peony (Paeonia suffruticosa Andrews), a woody deciduous shrub, belongs to the section Moutan DC. in the genus of Paeonia of the Paeoniaceae family. To increase the efficiency of breeding, two EST-derived marker systems were developed based on a tree peony expressed sequence tag (EST) database. Using target region amplification polymorphism (TRAP), 19 of 39 primer pairs showed good amplification for 56 accessions with amplicons ranging from 120 to 3,000 bp long, among which 99.3% were polymorphic. In contrast, 7 of 21 primer pairs demonstrated adequate amplification with clear bands for simple sequence repeats (SSRs) developed from ESTs, and a total of 33 alleles were found in 56 accessions. The similarity matrices generated by TRAP and EST-SSR markers were compared, and the Mantel test (r = 0.57778, P = 0.0020) showed a moderate correlation between the two types of molecular markers. TRAP markers were suitable for DNA fingerprinting and EST-SSR markers were more appropriate for discriminating synonyms (the same cultivars with different names due to limited information exchanged among different geographic areas). The two sets of EST-derived markers will be used further for genetic linkage map construction and quantitative trait locus detection in tree peony. PMID:21987120

  13. Differential effects of quercetin glycosides on GABAC receptor channel activity.

    PubMed

    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

    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

  14. Simultaneous determination of quercetin and its glycosides from the leaves of Nelumbo nucifera by reversed-phase high-performance liquid chromatography

    Microsoft Academic Search

    Hyun Ryul Goo; Jae Sue Choi; Dong Hee Na

    2009-01-01

    The purpose of this study was to develop reversed-phase HPLC method for the simultaneous determination of the flavonoids from\\u000a the leaves of Nelumbo nucifera, which have been known to exhibit antioxidant, anti-HIV, antihyperlipidemic and antiobesity effects. HPLC separation was\\u000a achieved on C18 column using gradient elution with mobile phase consisting of acetonitrile-water containing 0.1% formic acid. The separated\\u000a peaks were

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

    PubMed Central

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

    2011-01-01

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

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

    PubMed

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

    2015-07-15

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

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

    PubMed

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

    2014-11-01

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

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

    NASA Astrophysics Data System (ADS)

    K?en, Vladimír

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

  19. [Flavonol glycosides from Lysimachia clethroides].

    PubMed

    Liang, Dong; Liu, Yan-Fei; Hao, Zhi-You; Luo, Huan; Wang, Yan; Zhang, Chun-Lei; Zhang, Qing-Jian; Chen, Ruo-Yun; Yu, De-Quan

    2015-01-01

    Eleven flavonol glycosides were isolated from the ethanol extract of Lysimachia clethroides by a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified as astragalin (1), isoquercitrin (2), isorhamnetin-3-O-?-D-glucopyranoside (3), quercetin-3-O-?-D-6"-acetylglucopyranoside (4), quercetin-7-O-?-D-glucopyranoside (5), prunin (6), 2-hydroxynaringin-5-O-?-D-glucopyranoside (7), kaempferol-3-O-rutinonoside (8), kaempferol-3-O-robinobioside (9), rutin (10) and kaempferol-3,7-di-O-?-D-glucopyranoside (11). Among them, compounds 4, 7 and 11 were obtained from the Lysimachia genus for the first time, while compounds 3, 5 and 9 were firstly reported from this plant. In the preliminary assays, compounds 2, 6 and 8 possessed significant inhibition against aldose reduc- tase, with IC50 values of 2.69, 1.00, 1.80 ?mol · L(-1), respectively; none of compounds 1-11 exhibited obvious cytotoxic activity (IC50 > 10 ?mol · L(-1)). PMID:25993797

  20. Glycosides from Bougainvillea glabra

    Microsoft Academic Search

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

    2006-01-01

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

  1. Cardiac glycosides from erysimum cheiranthoides.

    PubMed

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

    1998-11-20

    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

  2. Naturally occurring methyl salicylate glycosides.

    PubMed

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

    2014-01-01

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

  3. Improved HPLC method for the evaluation of the major steviol glycosides in leaves of Stevia rebaudiana

    Microsoft Academic Search

    Ursula Woelwer-Rieck; Christa Lankes; Andreas Wawrzun; Matthias Wüst

    2010-01-01

    A simple reversed-phase high-performance liquid chromatographic method has been developed for the determination of the major\\u000a steviol glycosides, the diterpene sweeteners derived from Stevia rebaudiana. The method is based on a water extraction step and a solid-phase extraction (SPE) clean-up. Different SPE cartridges and\\u000a two HPLC columns were tested in the separation of the main steviol glycosides stevioside and rebaudioside

  4. Effect of marine glycosides on adenosinetriphosphatase activity.

    PubMed

    Gorshkov, B A; Gorshkova, I A; Stonik, V A; Elyakov, G B

    1982-01-01

    Marine glycosides from the sea cucumbers Actinopyga agassizi, Holothuria atra, Bohadschia argus, Cucumaria fraudatrix, Astichopus multifidus and Thelenota ananas inhibit both Na+-K+ ATPase and Mg2+-ATPase of rat brain in vitro. The glycoside-cholesterol complex of these compounds does not influence ATPase activity. Asterosaponins from starfishes Linckia guildingi and Linckia laevigata possess a slight inhibiting effect. The triterpene glycosides from sea cucumbers are more powerful inhibitors than steroidal glycosides from starfishes. PMID:6213068

  5. Effect of root length on epicotyl dormancy release in seeds of Paeonia ludlowii, Tibetan peony

    PubMed Central

    Hao, Hai-ping; He, Zhi; Li, Hui; Shi, Lei; Tang, Yu-Dan

    2014-01-01

    Background and Aims Epicotyl dormancy break in seeds that have deep simple epicotyl morphophysiological dormancy (MPD) requires radicle emergence and even a certain root length in some species. However, the mechanisms by which root length affects epicotyl dormancy break are not clear at present. This study aims to explore the relationship between root length and epicotyl dormancy release in radicle-emerged seeds of Tibetan peony, Paeonia ludlowii, with discussion of the possible mechanisms. Methods Radicle-emerged seeds (radicle length 1·5, 3·0, 4·5 and 6·0 cm) were incubated at 5, 10 and 15 °C. During the stratification, some seeds were transferred to 15 °C and monitored for epicotyl–plumule growth. Hormone content was determined by ELISA, and the role of hormones in epicotyl dormancy release was tested by exogenous hormone and embryo culture. Key Results Cold stratification did not break the epicotyl dormancy until the root length was ?6 cm. The indole-3-actic acid (IAA) and GA3 contents of seeds having 6 cm roots were significantly higher than those of seeds with other root lengths, but the abscisic acid (ABA) content was lowest among radicle-emerged seeds. GA3 (400 mg L?1) could break epicotyl dormancy of all radicle-emerged seeds, while IAA (200 mg L?1) had little or no effect. When grown on MS medium, radicles of naked embryos grew and cotyledons turned green, but epicotyls did not elongate. Naked embryos developed into seedlings on a mixed medium of MS + 100 mg L?1 GA3. Conclusions A root length of ?6·0 cm is necessary for epicotyl dormancy release by cold stratification. The underlying reason for root length affecting epicotyl dormancy release is a difference in the GA3/ABA ratio in the epicotyl within radicle-emerged seeds, which is mainly as a result of a difference in ABA accumulation before cold stratification. PMID:24284815

  6. [Phenyl glycosides from Curculigo orchioides].

    PubMed

    Xu, J P; Xu, R S

    1992-01-01

    One new phenyl glycoside and two new chlorophenyl glycosides were isolated from rhizomes of Curculigo orchioides (Chinese name: Xian Mao, Hypoxidaceae). Based on HRMS, FABMS, 1H-, 13C-NMR and other spectral data as well as chemical evidence, the structures of curculigoside B, curculigine B and C were elucidated to be 2-beta-D-glucopyranosyloxy-5-hydroxybenzyl-2'-methoxy-6'-hydroxybe nzoate (I),24-dichloro-3-methyl-5-methoxy-phenol-O-beta-D-apiofuranosyl (1-6)-beta-D-glucopyanoside (III) and 2,4,6-trichloro-3-methyl-5-methoxyphenol-O-beta-D-xylopyranosyl (1-6)-beta-D-glucopyranoside (IV), respectively. PMID:1442056

  7. Phenolic glycosides from Phagnalon rupestre

    Microsoft Academic Search

    Luis Góngora; Salvador Máńez; Rosa M Giner; M Carmen Recio; Alexander I Gray; José-Luis R??os

    2002-01-01

    Analysis of the butanol-soluble fraction from the methanolic extract of the aerial parts of Phagnalon rupestre (Asteraceae) has led to the isolation of seven phenolic compounds. Three have been identified on the basis of their NMR spectra as new natural compounds: the lignan 7,7?-bis-(4-hydroxy-3,5-dimethoxyphenyl)-8,8?-dihydroxymethyl-tetrahydrofuran-4-O-?-glucopyranoside (1), the prenylhydroquinone glycoside 1-O-?-glucopyranosyl-1,4-dihydroxy-2-(3?-hydroxy-3?-methylbutyl) benzene (2) and the acetophenone glycoside 12-O-?-glucopyranosyl-9?,12-dihydroxytremetone (3). The known flavonoids

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

    PubMed

    Huang, Xiangdong; Xue, Dong; Xue, Lian

    2015-08-01

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

  9. Flavanone glycosides from Alhagi pseudalhagi.

    PubMed

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

    1999-06-01

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

  10. Cardiac glycosides from Erysimum cheiranthoides.

    PubMed

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

    2000-02-01

    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

  11. Megastigmane glycosides from Salvia nemorosa

    Microsoft Academic Search

    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

    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.

  12. Megastigmane glycosides from Salvia nemorosa.

    PubMed

    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

    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

  13. [The antifungal action of polygalacic acid glycosides].

    PubMed

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

    1990-07-01

    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

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

    PubMed

    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

    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

  15. Schoepfiajasmins A-H: C-glycosyl dihydrochalcones, dihydrochalcone glycoside, C-glucosyl flavanones, flavanone glycoside and flavone glycoside from the branches of Schoepfia jasminodora.

    PubMed

    Ukida, Kouki; Doi, Takashi; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki; Takeda, Yoshio

    2013-01-01

    From the branches of Schoepfia jasminodora collected in Okinawa, three new dihydrochalcone C-glycosides, one dihydrochalcone di-O-glucopyranoside, two flavanone C-glycosides, one flavanone O-glycoside and one flavone O-glycoside were isolated. Their structures were elucidated by extensive study of one- and two-dimensional NMR spectroscopic data. PMID:24189301

  16. Cardiac glycosides from Erysimum cheiranthoides.

    PubMed

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

    2002-06-01

    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

  17. Two phenolic glycosides from Curculigo orchioides Gaertn.

    PubMed

    Dall'Acqua, Stefano; Shrestha, Bharat Babu; Comai, Stefano; Innocenti, Gabbriella; Gewali, Mohan Bikram; Jha, Pramod Kumar

    2009-07-01

    One new glycoside derivative from syringic acid and one new phenol glycoside, curculigoside E (1) and orchioside D (2), were isolated and characterized from the rootstock of Curculigo orchioides collected in the Nawalparasi District (Nepal). The structures of the new isolated compounds were elucidated by means of spectroscopic methods such as 1D, 2D NMR and MS. PMID:19285123

  18. 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...

  19. Immunological detection of cardiac glycosides in plants.

    PubMed

    Radford, D J; Cheung, K; Urech, R; Gollogly, J R; Duffy, P

    1994-08-01

    Australian native and introduced plants were examined, using digoxin immunoassays, to detect the presence of cross-reacting cardiac glycosides. These compounds were found in 27 species from 20 genera. The assay technique can also be used on serum samples to confirm cardiac glycoside ingestion. PMID:7986184

  20. Phenolic glycosides from Curculigo orchioides Gaertn.

    PubMed

    Wang, Zhen-Hui; Huang, Jian; Ma, Xiao-Ci; Li, Guo-Yu; Ma, Yue-Ping; Li, Ning; Wang, Jin-Hui

    2013-04-01

    Five new chlorophenolic glucosides, curculigine E (1), curculigine F (2), curculigine G (3), curculigine H (5), curculigine I (6) and one new phenolic glycoside, orcinoside H (4), together with eight known phenolic glycosides (7-14) were isolated from the Curculigo orchioides Gaertn. Their structures were established by spectroscopic techniques (IR, UV, MS, 1D and 2D NMR). The isolated phenolic glycosides were evaluated for antiosteoporotic activity against MC3T3-E1 cell line using MTT assays. Compounds 1, 2, 3, and 5 showed moderate antiosteoporotic activity with the proliferation rate of 10.1-14.1%. PMID:23353659

  1. Flavanone glycosides from Miconia trailii.

    PubMed

    Zhang, Zhizhen; ElSohly, Hala N; Li, Xing-Cong; Khan, Shabana I; Broedel, Sheldon E; Raulli, Robert E; Cihlar, Ronald L; Walker, Larry A

    2003-01-01

    Assay-guided fractionation of the ethanol extract of the twigs and leaves of Miconia trailii yielded two new flavanone glycosides, matteucinol 7-O-alpha-l-arabinopyranosyl(1-->6)-beta-d-glucopyranoside (miconioside A, 1) and farrerol 7-O-beta-d-apiofuranosyl(1-->6)-beta-d-glucopyranoside (miconioside B, 2), along with the known compounds matteucinol 7-O-beta-d-apiofuranosyl(1-->6)-beta-d-glucopyranoside (3), matteucinol (4), 2alpha,3beta,19alpha-trihydroxyolean-12-ene-24,28-dioic acid (bartogenic acid, 5), 2alpha,3beta,23-trihydroxyolean-12-ene-28-oic acid (arjunolic acid, 6), 2alpha,3alpha,19alpha, 23-tetrahydroxyurs-12-ene-28-oic acid (myrianthic acid, 7), and stigmast-4-ene-3,6-dione (8). The structures of 1-8 were elucidated by spectroscopic methods, including 2D NMR. PMID:12542342

  2. Synthesis of the Rhodiola rosea glycoside rosavin

    Microsoft Academic Search

    S. A. Patov; V. V. Punegov; A. V. Kuchin

    2006-01-01

    A synthetic scheme was proposed for the glycoside rosavin that includes a one-step glycosylation of cinnamyl alcohol with\\u000a a disaccharide. The structure of the product was confirmed by PMR and 13C NMR spectroscopy.

  3. Triterpene glycosides of Dianthus deltoides. I

    Microsoft Academic Search

    V. G. Bukharov; S. P. Shcherbak; A. P. Beshchekova

    1971-01-01

    Summary FromDianthus deltoides L. we have isolated three new triterpene glycosides: dianthosides A, B, and C. It has been shown that dianthoside A is the 3-O-ß-glucopyranoside and dianthoside B the 3-O-[O-ß-D-glucopyranosyl-(1 ? 6)-ß-glucopyranoside] of gypsogenic acid. Some information on the structure of dianthoside C — a new glycoside of gypsogenin — has been obtained.

  4. Two Flavonoid Glycosides from Cassia occidentalis Pods.

    PubMed

    Singh, M; Singh, J

    1985-12-01

    From the ethanolic extract of the pods of CASSIA OCCIDENTALIS, two flavonoid glycosides namely 3,5,3',4'-tetrahydroxy-7-methoxyflavone 3- O-(2''-rhamnosyl glucoside) and 5,7,4'-trihydroxy-3,6,3'-trimethoxy-flavone 7- O-(2''-rhamnosyl glucoside) have been isolated and their structures characterised. Both these aglycones (1, 2) are known but their glycosides are being reported for the first time. PMID:17345279

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

    PubMed Central

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

    2015-01-01

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

  6. Simultaneous analysis of cardiac glycosides in blood and urine by thermoresponsive LC-MS-MS

    Microsoft Academic Search

    Sanae Kanno; Kanako Watanabe; Itaru Yamagishi; Seishiro Hirano; Kayoko Minakata; Kunio Gonmori; Osamu Suzuki

    2011-01-01

    A new thermoresponsive polymer separation column was applied to simultaneous analysis of four cardiac glycosides (CGs) being\\u000a widely used for the treatment of arrhythmias and heart failure in human blood and urine. This column is composed of an N-isopropylacrylamide polymer, the surface of which undergoes a reversible alteration from hydrophilic to hydrophobic by changing\\u000a temperature. The chromatographic separation and retention

  7. FLAVONE C-GLYCOSIDES AND CUCURBITACIN GLYCOSIDES FROM CITRULLUS COLOCYNTHIS

    Microsoft Academic Search

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

    2006-01-01

    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

  8. Diterpene glycosides from Stevia phlebophylla A. Gray.

    PubMed

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

    2013-09-20

    The rare Mexican species Stevia phlebophylla A. Gray was long considered to be the only known Stevia species, beside the well-known S. rebaudiana, containing the highly sweet diterpenoid steviol glycosides. We report a re-evaluation of this claim after phytochemically screening leaves obtained from two herbarium specimens of S. phlebophylla for the presence of steviol glycosides. Despite extensive MS analyses, no steviol glycosides could be unambiguously verified. Instead, the main chromatographic peak eluting at retention times similar to those of steviol glycosides was identified as a new compound, namely 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

  9. The insulin receptor glycosidic moiety : its characterization and role

    E-print Network

    Paris-Sud XI, Université de

    The insulin receptor glycosidic moiety : its characterization and role Martine CARON, Gisčle exoglycosidases and/or lectins as specific glycosidic probes, we characterized the insulin receptor carbohydrate components in normal or transformed cells and investigated their importance in the insulin

  10. Peony-Glycyrrhiza Decoction, an Herbal Preparation, Inhibits Clozapine Metabolism via Cytochrome P450s, but Not Flavin-Containing Monooxygenase in In Vitro Models.

    PubMed

    Wang, Wei; Tian, Dan-Dan; Zheng, Bin; Wang, Di; Tan, Qing-Rong; Wang, Chuan-Yue; Zhang, Zhang-Jin

    2015-07-01

    Our previous studies have shown the therapeutic efficacy and underlying mechanisms of Peony-Glycyrrhiza Decoction (PGD), an herbal preparation, in treating antipsychotic-induced hyperprolactinemia in cultured cells, animal models, and human subjects. In the present study, we further evaluated pharmacokinetic interactions of PGD with clozapine (CLZ) in human liver microsomes (HLM), recombinantly expressed cytochrome P450s (P450s), and flavin-containing monooxygenases (FMOs). CLZ metabolites, N-demethyl-clozapine and clozapine-N-oxide, were measured. PGD, individual peony and glycyrrhiza preparations, and the two individual preparations in combination reduced production of CLZ metabolites to different extents in HLM. While the known bioactive constituents of PGD play a relatively minor role in the kinetic effects of PGD on P450 activity, PGD as a whole had a weak-to-moderate inhibitory potency toward P450s, in particular CYP1A2 and CYP3A4. FMOs are less actively involved in mediating CLZ metabolism and the PGD inhibition of CLZ. These results suggest that PGD has the capacity to suppress CLZ metabolism in the human liver microsomal system. This suppression is principally associated with the inhibition of related P450 activity but not FMOs. The present study provides in vitro evidence of herb-antipsychotic interactions. PMID:25948710

  11. Steviol glycosides: chemical diversity, metabolism, and function.

    PubMed

    Ceunen, Stijn; Geuns, Jan M C

    2013-06-28

    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

  12. Quantification of appetite suppressing steroid glycosides from Hoodia gordonii in dried plant material, purified extracts and food products using HPLC-UV and HPLC-MS methods.

    PubMed

    Janssen, Hans-Gerd; Swindells, Chris; Gunning, Philip; Wang, Weijun; Grün, Christian; Mahabir, Krishna; Maharaj, Vinesh J; Apps, Peter J

    2008-06-01

    High-performance liquid chromatography (HPLC)-UV and HPLC-Mass Spectrometry (MS) methods were developed for the quantitative analysis of the family of Hoodia gordonii steroid glycosides with appetite suppressing properties in dried plant material, in purified and enriched extracts and in various prototype food-products fortified with H. gordonii extracts. For solid materials, e.g. dried plants or for non-fatty foods, extraction of the steroid glycosides is performed using methanol. For products where the steroid glycosides are present in an oil matrix, direct injection of the oil after dilution in tetrahydrofuran is applied. The HPLC separation is performed on an octyl-modified reversed-phase column in the gradient mode with UV detection at lambda = 220 nm. Quantification is performed against an external calibration line prepared using either one of the pure steroid glycosides or geranyl-tiglate. Short- and long-term repeatabilities of the methods are better than 3 and 6%, respectively. Recoveries are better than 85%, even in the analysis of the least abundant steroid glycosides in a complex yoghurt drink. Linearity is better than 3-4 orders of magnitude and the detection limits are below approximately 2 microg g(-1) for the individual steroid glycosides in dried plant material and food products. HPLC-MS is used to confirm that the steroid glycosides contain the characteristic steroid core, the carbohydrate chain and the tigloyl group. PMID:18486659

  13. Neolignan and flavonoid glycosides in Juniperus communis var. depressa

    Microsoft Academic Search

    Tsutomu Nakanishi; Naoki Iida; Yuka Inatomi; Hiroko Murata; Akira Inada; Jin Murata; Frank A. Lang; Munekazu Iinuma; Toshiyuki Tanaka

    2004-01-01

    Two neolignan glycosides (junipercomnosides A and B) were isolated from aerial parts of Juniperus communis var. depressa along with two known neolignan glycosides and seven flavonoid glycosides. The structures of the isolated compounds were determined by spectral analysis, in particular by 2D-NMR analysis. The significance of distribution of flavonoids in the chemotaxonomy of genus Juniperus was also discussed.

  14. Plant cardiac glycosides and digoxin Fab antibody.

    PubMed

    Cheung, K; Urech, R; Taylor, L; Duffy, P; Radford, D

    1991-10-01

    The potential application of the Digoxin Fab antibody (Wellcome Digibind) in the clinical management of plant poisoning was investigated. The cardiac glycoside contents of various Australian plants were studied using immunoassay techniques. The cross-reactions of the Fab antibody and two digoxin assay antibodies against extracts of these plants were also studied. Results obtained indicated that the Digibind antibody cross-reacted with a wide range of glycosides contained in Australian plants and therefore could be of use in the treatment of life-threatening plant poisoning. PMID:1931226

  15. Flavanone and diphenylpropane glycosides and glycosidic acyl esters from Viscum articulatum.

    PubMed

    Kuo, Yu-Jen; Yang, Yu-Ching; Zhang, Li-Jie; Wu, Ming-Der; Kuo, Li-Ming Yang; Kuo, Yuh-Chi; Hwang, Syh-Yuan; Chou, Cheng-Jen; Lee, Kuo-Hsiung; Ho, Hsiu-O; Kuo, Yao-Haur

    2010-02-26

    Seven new compounds including three flavanone glycosides, visartisides A-C (1-3), three glycoside acyl esters, visartisides D-F (4-6), and one diphenylpropane glycoside, (4'-hydroxy-2',3',6',3''-tetramethoxy-1,3-diphenylpropane)-4''-O-beta-d-glucopyranoside (7), along with four known flavanone glycosides (8-11) were isolated from the leaves and stems of Viscum articulatum. The structure elucidation of 1-7 was based on spectroscopic data analysis. Biological evaluation showed that 1, 2, and 10 exhibited antioxidant activity using a DPPH method and that compounds 1, 3, and 11 were active in a lipopolysaccharide-induced nitric oxide assay. PMID:20121165

  16. Enzymatic Processing of Bioactive Glycosides from Natural Sources

    NASA Astrophysics Data System (ADS)

    Weignerová, Lenka; K?en, Vladimír

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

  17. Mechanisms for nucleophilic aliphatic substitution at glycosides

    Microsoft Academic Search

    Nicole A. Horenstein

    2006-01-01

    Much of carbohydrate chemistry and biochemistry is centered on bond forming and bond breaking reactions at the anomeric carbon of glycosides. No single mechanism adequately covers the scope of these reactions, because differences in sugar substituents, stereochemistry, leaving groups, nucleophiles, and catalysts can influence the mechanistic pathway taken. The influence of solvent is only now beginning to become apparent in

  18. Two new secoiridoid glycosides from Gentiana algida.

    PubMed

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

    1997-12-01

    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

  19. Antifungal steroid glycoside from sea cucumber.

    PubMed

    Shimada, S

    1969-03-28

    An antifungal steroid glycoside, holotoxin, has been isolated from the sea cucumber Stichopus japonicus (Selenka). In vitro, it exhibits high activity against various fungi, including vegetable pathogens, but has scarcely any activity against Gram-positive and Gram-negative bacteria and mycobacteria in vitro. PMID:5812983

  20. Four new glycosides from Pleurospermum franchetianum

    Microsoft Academic Search

    Ying-Gang Luo; Bo-Gang Li; Guo-Lin Zhang

    2002-01-01

    Four new glycosides, pleurofranosides I-IV, together with eight known compounds were isolated from the whole plants of Pleurospermum franchetianum Hemsl. Based on the spectral data and chemical evidence, the structures of pleurofranosides I, II, III and IV were elucidated to be 16 g , 21 g , 23, 28-tetrahydroxyolean-12-ene-3 g -yl- O - g - d -glucopyranosyl-(1 M 2)- g

  1. Flavonoid glycosides and limonoids from Citrus molasses.

    PubMed

    Kuroyanagi, Masanori; Ishii, Hiromi; Kawahara, Nobuo; Sugimoto, Hiroyuki; Yamada, Hideo; Okihara, Kiyoshi; Shirota, Osamu

    2008-01-01

    Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice production. This molasses is expected to be a useful source of organic compounds such as flavonoids and limonoids. To elucidate a use for this molasses waste, we isolated and identified its organic constituents. Two new flavanonol glycosides were isolated from tangerine orange molasses, along with several flavonoids such as hesperidine, narirutin, eriodictyol, 3',4',5,6,7,8-hexamethoxy-3-O-beta-D-glucopyranosyloxyflavone, and 3',4',5,6,7,8-hexamethoxy- 3-beta-D-[4-O-(3-hydroxy-3-methylglutaloyl)]-glucopyranosyloxyflavone, and limonoids such as limonin, nomilin, and cyclic peptide, citrusin III. The structures of the new flavanonol glycosides were determined as (2R,3R)-7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-aromadendrin and 7-O-(6-O-alpha-L-rahmnopyranosyl-beta-D-glucopyranosyl)-3,3',5,7-tetrahydroxy-4'-methoxyflavanone by means of spectral analyses using (1)H-NMR, (13)C-NMR, and 2D-NMR. Of these compounds, flavanone glycoside, hesperidin and narirutin were isolated as the main constituents. Thus, molasses is a promising source of flavonoid glycosides. PMID:18404354

  2. A flavone glycoside from Andrographis alata

    Microsoft Academic Search

    A. G. Damu; B. Jayaprakasam; K. V. Rao; D. Gunasekar

    1998-01-01

    A new flavone glycoside, echioidinin 5-glucoside along with its known aglycone, echioidinin have been isolated from the whole plant of Andrographis alata. The structure of the new compound was established as 5,2?-dihydroxy-7-methoxyflavone 5-O-?-d-glucopyranoside on the basis of spectral and chemical studies.

  3. A flavone glycoside from Andrographis alata.

    PubMed

    Damu, A G.; Jayaprakasam, B; Rao, K V.; Gunasekar, D

    1998-11-20

    A new flavone glycoside, echioidinin 5-glucoside along with its known aglycone, echioidinin have been isolated from the whole plant of Andrographis alata. The structure of the new compound was established as 5,2'-dihydroxy-7-methoxyflavone 5-O-beta-D-glucopyranoside on the basis of spectral and chemical studies. PMID:11711108

  4. Two new triterpenoid glycosides from Curculigo orchioides.

    PubMed

    Zuo, Ai-Xue; Shen, Yong; Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhou, Jun; Lü, Jun; Chen, Ji-Jun

    2012-01-01

    Two new cycloartane triterpenoid glycosides, named curculigosaponin N and curculigosaponin O, were isolated from rhizomes of Curculigo orchioides Gaertn. Their structures were elucidated on the basis of comprehensive spectroscopic analysis including IR, MS, 1D, and 2D NMR (HSQC and HMBC). PMID:22316001

  5. Neoconvallatoxoloside — A cardenolide glycoside from Convallaria majalis

    Microsoft Academic Search

    Ya. Bochvarov; N. F. Komissarenko

    1977-01-01

    Summary  A new cardinolide glycoside has been isolated from the leaves ofConvallaria majalis L.; it has been called neoconvallatoxolisode and its structure has been established as strophanthidol 3-O-[O-?-D-glucopyranosyl-(1 ? 2)-?-L-rhamnopyranoside].

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

    NASA Astrophysics Data System (ADS)

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

    2011-06-01

    Previously, hydrothermally prepared mesoporous peony-like ceria (PCO) material was shown to exhibit superior catalytic properties for CO oxidation and ethanol reforming. Ni supported PCO had been shown to have high activity for ethanol steam reforming at low temperature. In this work, Ag, Cu and Mn is co-loaded with Ni on PCO catalysts by impregnation method. The catalysts were studied by X-ray diffraction (XRD), scanning electron microscopy (SEM), and a combined thermogravimetry, differential scanning calorimetry, and mass spectrometry (TG-DSC-MS). It was found that all the catalysts gave 100% ethanol conversion above ca. 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.

  7. Triterpene glycosides of Sophora japonica seeds

    Microsoft Academic Search

    V. I. Grishkovets; L. A. Gorbacheva

    1995-01-01

    We have isolated from the seeds of Sophora japonica the known soyasaponogenol B-3-[O-ß-D-glucopyranosyl-(1?2)-O-ß-D-glucopyranuronoside] (adzukisaponin II), soyasapogenol B [3-O-ß-galactopyranosyl-(1?2)-O-ß-L-glucopyranuronoside] (soyasaponin III), soyasapogenol B 3-(O-a-L-rhamnopyranosyl-(1?2)-O-ß-L-glucopyranosyl-(1?2)-O-ß-D-glucopyranuronoside] (adzukisaponin V), soyasapogenol B 3-(O-ß-D-rhamnopyranosyl-(1?2)-O-ß-D-galactopyranosyl-(1?2)-O-ß-D-glucopyranuronoside] (soyasaponin I), and the new glycoside (1) — soyasapogenol B 3-[O-ß-D-glucopyranuronoside]. The structure of this glycoside has been established on the basis of the results of enzymatic, complete, and partial hydrolyses and13C

  8. Detection of Triterpenoid Glycosides on Paper Chromatograms

    Microsoft Academic Search

    I. Belic

    1956-01-01

    IN the course of our investigations of Echinocystis lobata seeds, it became desirable to locate triterpenoid glycosides on paper chromatograms by means of a colour reaction. A modification of the Liebermann-Burchard test described by Neher and Wettstein1 was unsatisfactory for this purpose. We found that the original Liebermann-Burchard reaction applied to paper chromatograms with comparatively little alterations gave more satisfactory

  9. Cardiac glycosides in traditional Chinese medicine

    Microsoft Academic Search

    Lu Fu-hua

    1987-01-01

    Summary  The effect of cardiac glycosides containing medicinal herbs, e.g. Ting Li Zi (Descurainia sophia), against heart failure was detected by traditional Chinese doctors at the beginning of the first century, more than 16 centuries\\u000a before Withering’s discovery of digitalis to promote diuresis. We ran infer the diagnosis from the description of the symptom\\u000a complex, for which the herb as the

  10. Chalconoid and stilbenoid glycosides from Guibourtia tessmanii

    Microsoft Academic Search

    V Fuendjiep; J Wandji; F Tillequin; D. A Mulholland; H Budzikiewicz; Z. T Fomum; A. M Nyemba; M Koch

    2002-01-01

    Phytochemical studies on the stem bark of Guibourtia tessmanii yielded a dihydrochalcone glucoside, 2?,4-dihydroxy-4?-methoxy-6?-O-?-glucopyranoside dihydrochalcone and a new stilbene glycoside, 3,5-dimethoxy-4?-O-(?-rhamnopyranosyl-(1?6)-?- glucopyranoside) stilbene besides the known pterostilbene. Their structures were established on the basis of one and two dimensional NMR spectroscopic techniques, FABMS and chemical evidence.

  11. [Two new flavanone glycosides from Glycyrrhizia inflata].

    PubMed

    Wang, B; Zou, K; Yang, X B; He, W Y; Zhao, Y Y; Zhang, R Y

    1997-01-01

    Two new flavanone glycosides having two chains of sugar moeity were isolated from the roots of Glycyrrhizia inflata Bat by repeated CC and HPLC. They were identified to be liquiritigenin-7-O-beta-D-apiofuranosyl-4'-O-beta-D-glucopyranoside(I) and liquiritigenin-7-O-beta-D-(3-O-acetyl)-apiofuranosyl-4'-O-beta-D- glucopyranoside (II) on the basis of chemical and spectroscopic methods. PMID:11327021

  12. Flavonoid glycosides and limonoids from Citrus molasses

    Microsoft Academic Search

    Masanori Kuroyanagi; Hiromi Ishii; Nobuo Kawahara; Hiroyuki Sugimoto; Hideo Yamada; Kiyoshi Okihara; Osamu Shirota

    2008-01-01

    Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice production. This molasses is expected to\\u000a be a useful source of organic compounds such as flavonoids and limonoids. To elucidate a use for this molasses waste, we isolated\\u000a and identified its organic constituents. Two new flavanonol glycosides were isolated from

  13. Chalconoid and stilbenoid glycosides from Guibourtia tessmanii.

    PubMed

    Fuendjiep, V; Wandji, J; Tillequin, F; Mulholland, D A; Budzikiewicz, H; Fomum, Z T; Nyemba, A M; Koch, M

    2002-08-01

    Phytochemical studies on the stem bark of Guibourtia tessmanii yielded a dihydrochalcone glucoside, 2',4-dihydroxy-4'-methoxy-6'-O-beta-glucopyranoside dihydrochalcone and a new stilbene glycoside, 3,5-dimethoxy-4'-O-(beta-rhamnopyranosyl-(1-->6)-beta- glucopyranoside) stilbene besides the known pterostilbene. Their structures were established on the basis of one and two dimensional NMR spectroscopic techniques, FABMS and chemical evidence. PMID:12150803

  14. ?-cyclodextrin assistant flavonoid glycosides enzymatic hydrolysis

    PubMed Central

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

    2013-01-01

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

  15. New maltol glycosides from Flos Sophorae.

    PubMed

    Zhang, Yi; Qu, Lu; Liu, Lili; Li, Xiaoxia; Liu, Erwei; Han, Lifeng; Fang, Shiming; Gao, Xiumei; Wang, Tao

    2015-04-01

    Three new maltol glycosides, designated soyamalosides A (1), B (2), and C (3), together with eight known compounds (4-11), were obtained from a 70 % EtOH extract of Flos Sophorae. Their structures were elucidated by chemical and spectroscopic methods. Of the known compounds, this is the first report of 4-6, 9, and 11 in the Sophora genus. Compounds 2, 3, and 10 showed significant protective effects against antimycin A-induced L6 cell injury. PMID:25398298

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

    Microsoft Academic Search

    Keiichi Matsuzaki; Rie Ishii; Kaori Kobiyama; Susumu Kitanaka

    2010-01-01

    New benzophenone and flavonol galloyl glycosides were isolated from an 80% MeOH extract of Psidium guajava L. (Myrtaceae) together with five known quercetin glycosides. The structures of the novel glycosides were elucidated to be\\u000a 2,4,6-trihydroxybenzophenone 4-O-(6?-O-galloyl)-?-d-glucopyranoside (1, guavinoside A), 2,4,6-trihydroxy-3,5-dimethylbenzophenone 4-O-(6?-O-galloyl)-?-d-glucopyranoside (2, guavinoside B), and quercetin 3-O-(5?-O-galloyl)-?-l-arabinofuranoside (3, guavinoside C) by NMR, MS, UV, and IR spectroscopies. Isolated phenolic glycosides

  17. DNA-N-Glycosylases Process Novel O-Glycosidic Sites in DNA†

    PubMed Central

    Admiraal, Suzanne J.; O'Brien, Patrick J.

    2013-01-01

    After hydrolyzing the N-glycosyl bond between a damaged base and C1' of a deoxyribosyl moiety of DNA, human alkyladenine DNA glycosylase (AAG) and E. coli 3-methyladenine DNA glycosylase II (AlkA) bind tightly to their abasic DNA products, potentially protecting these reactive species. Here we show that both AAG and AlkA catalyze reactions between bound abasic DNA and small, primary alcohols to form novel DNA-O-glycosides. The synthesis reactions are reversible, as the DNA-O-glycosides are converted back into abasic DNA when incubated with AAG or AlkA in the absence of alcohol. AAG and AlkA are therefore able to hydrolyze O-glycosidic bonds in addition to N-glycosyl bonds. The newly discovered DNA-O-glycosidase activities of both enzymes compare favorably with their known DNA-N-glycosylase activities: AAG removes both methanol and 1,N6-ethenoadenine (?A) from DNA with single turnover rate constants that are 2.9×105-fold greater than the corresponding uncatalyzed rates, whereas the rate enhancement of 3.7×107 for removal of methanol from DNA by AlkA is 300-fold greater than its rate enhancement for removal of ?A from DNA. Although the biological significance of the DNA-O-glycosidase reactions is not known, the evolution of new DNA repair pathways may be aided by enzymes that practice catalytic promiscuity, such as these two unrelated DNA glycosylases. PMID:23688261

  18. Analysis of flavanone-7-O-glycosides in citrus juices by short-end capillary electrochromatography.

    PubMed

    Desiderio, Claudia; De Rossi, Antonella; Sinibaldi, Massimo

    2005-07-15

    The separation of the major flavanone-7-O-glycoside constituents of Citrus was carried out by isocratic reversed phase capillary electrochromatography using a 75 microm i.d. silica fused column packed with 5 microm ODS silica gel. In comparison to HPLC mode, capillary electrochromatography resolution of flavanone glycosides was obtained with a high selectivity factor. Optimum separation conditions were found using a mixture of ammonium formate (pH 2.5)--acetonitrile (8:2, v/v) as the mobile phase by the short-end injection mode. Under these conditions all the investigated flavanones were baseline-resolved within short analysis time (i.e. between 5 and 10 min). A study, evaluating the intra- and inter-day repeatability as well as limit of detection and method linearity, was developed in accordance with the analytical procedures for method validation. The developed method was applied for the quantitative analysis of flavanone glycosides in commercial fruit juices (sweet orange, lemon and grapefruit). PMID:16013605

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

    PubMed

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

    2002-04-01

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

  20. Chromone glycosides and flavonoids from hypericum japonicum

    Microsoft Academic Search

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

    1998-01-01

    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

  1. Flavonol glycosides of Warburgia ugandensis leaves

    Microsoft Academic Search

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

    2003-01-01

    Four new flavonol glycosides: kaempferide 3-O-?-xylosyl (1?2)-?-glucoside, kaempferol 3-O-?-rhamnoside-7,4?-di-O-?-galactoside, kaempferol 3,7,4?-tri-O-?-glucoside and quercetin 3-O-[?-rhamnosyl (1?6)] [?-glucosyl (1?2)]-?-glucoside-7-O-?-rhamnoside, were characterized from a methanolic leaf extract of Warburgia ugandensis. The known flavonols: kaempferol, kaempferol 3-rhamnoside, kaempferol 3-rutinoside, myricetin, quercetin 3-rhamnoside, kaempferol 3-arabinoside, quercetin 3-glucoside, quercetin, kaempferol 3-rhamnoside-4?-galactoside, myricetin 3-galactoside and kaempferol 3-glucoside were also isolated. Structures were established by spectroscopic and chemical

  2. A new flavonoid glycoside from Vaccaria hispanica.

    PubMed

    Zhang, Haijiang; Wang, Kuiwu; Wu, Jie; Chen, Yao; He, Peipei

    2011-11-01

    A profiling analysis for the methanol extract of the seeds of Vaccaria hispanica (Mill.) Rauschert was performed using a HPLC-ESI-MS technique. Five compounds were identified according to their retention times, UV spectroscopic and MS features, and by comparison with literature data. Among them, a new flavonoid glycoside, named vaccarin H, was isolated and the structure determined by spectral and chemical analysis as isovitexin 2"-O-alpha-L-arabinopyranosyl-4'-O-(6"-O-dihydroferuloyl)-3-beta-glucopyranoside. PMID:22224271

  3. Glycosidic constituents from in vitro Anoectochilus formosanus.

    PubMed

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

    2000-11-01

    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

  4. Sesquiterpenoid tropolone glycosides from Liriosma ovata.

    PubMed

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

    2015-02-27

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

  5. Triterpene glycosides from the cultures of Phytolacca americana.

    PubMed

    Takahashi, H; Namikawa, Y; Tanaka, M; Fukuyama, Y

    2001-02-01

    A new triterpene glycoside I was isolated together with the five known triterpene glycosides 2-6 from the cultures of Phytolacca americana. The structure of 1 was elucidated by analysis of spectroscopic data and comparison of its NMR data with those of 2-7 and chemical degradation. PMID:11217119

  6. Quercetin glycosides from European aquatic Ranunculus species of subgenus Batrachium

    Microsoft Academic Search

    K. Gluchoff-Fiasson; J. L. Fiasson; H. Waton

    1997-01-01

    A chemical investigation of the leaves of aquatic Ranunculus species yielded six quercetin glycosides and eight acylated quercetin glycosides, three of which are reported for the first time: quercetin 3-(6?-malonylglucoside)-7-glucoside and the partially characterized quercetin 3-caffeylsophoroside-7-caffeylglucoside and quercetin 3-caffeylsophoroside-7-ferulylglucoside. © 1997 Elsevier Science Ltd. All rights reserved

  7. Acetylated flavanone glycosides from the rhizomes of Cyclosorus acuminatus.

    PubMed

    Fang, Wei; Ruan, Jinlan; Wang, Zhong; Zhao, Zhongxiang; Zou, Jian; Zhou, Daonian; Cai, Yaling

    2006-11-01

    Six new flavanone glycosides (1-6) were isolated from the methanol extract of the rhizomes of Cyclosorus acuminatus, together with the parent flavanone glycoside 2a. Their structures were established on the basis of spectroscopic and chemical methods. All compounds showed moderate activity against Streptococcus pneumoniae and Haemophilus influenzae. PMID:17125239

  8. Identification of natural epimeric flavanone glycosides by NMR spectroscopy

    Microsoft Academic Search

    Federica Maltese; Cornelis Erkelens; Frank van der Kooy; Young Hae Choi; Robert Verpoorte

    2009-01-01

    Recently advanced analytical technology has provided evidence of the existence of stereoisomers of many natural products. Particularly, flavanones which might have two different configurations at C-2 exist in many food additives, e.g., citrus fruits. In this study, the possible stereoisomers of flavanone glycosides were identified by NMR spectroscopy. Based on NMR spectra of common flavanone glycosides such as naringin, hesperidin,

  9. Flavonol glycosides from flowers of Crocus speciosus and C. antalyensis

    Microsoft Academic Search

    Rikke Nřrbćk; Tadao Kondo

    1999-01-01

    From the flower extracts of Crocus speciosus and C. antalyensis nine flavonol glycosides have been isolated. One of these products is a new flavonol glycoside identified as kaempferol 3-O-?-(2,3-di-O-?-d-glucopyranosyl)rhamnopyranoside by UV, mass and NMR spectroscopy.

  10. Cycloartane glycosides from the rhizomes of Curculigo orchioides.

    PubMed

    Yokosuka, Akihito; Sato, Koji; Mimaki, Yoshihiro

    2010-12-01

    Cycloartane glycosides (1-9) were isolated from rhizomes of Curculigo orchioides (Hypoxidaceae), and this structures were determined by spectroscopic analysis and a few chemical transformations. Cytotoxic activity of glycosides (1-9) and their common aglycone (1a) against HL-60 human promyelocytic leukemia cells was also examined. PMID:20965526

  11. Rebaudioside, a novel agent of glycoside clathration of pharmacons

    Microsoft Academic Search

    T. G. Tolstikova; A. O. Bryzgalov; M. V. Khvostov; G. A. Tolstikov

    2009-01-01

    Glycyrrhizinic acid and stevioside, glycosides of higher terpenoids, are capable of in vivo formation of clathrates with pharmacons with various types of activity. This property of glycosides allows the effective dose to be substantially decreased (by a factor of 10? 100), with the basic activity being preserved and novel pharmacological effects appearing [1?6]. The plant Stevia rebaudiana Bertoni is known

  12. HPLC determination of the flavonoid glycosides from Betulae folium extracts

    Microsoft Academic Search

    P. G. Pietta; P. L. Mauri; E. Manera; P. L. Ceva

    1989-01-01

    The main flavonoid glycosides ofBetulae folium extracts (quercetin-3-glucuronide, myricetin-3-galactoside, hyperosid, quercetin-3-arabinoside and quercetin-3-rhamnoside) have been separated by isocratic elution on a C18 Aquapore RP-300 column. Elution was performed with 17% isopropanol at pH 6.2 confirming the validity of this eluent for the analysis of the flavonoid glycosides.

  13. Therapeutic effect of compound of White Peony Root Oral Liquids on radiation-induced esophageal toxicity via the expression of EGF and TGF-?1

    PubMed Central

    SHEN, LI; LI, XING; SHAN, BAOEN; ZHANG, LI; GONG, YANJUN; DONG, ZHIMING; WANG, ZHIYU

    2013-01-01

    The predominant pathological processes of radiation-induced esophageal toxicity include inflammatory reactions in the early stage and the fibrotic process in the late stage. An increased expression of the epidermal growth factor (EGF) and transforming growth factor ?1 (TGF-?1) is capable of reducing inflammatory reactions and TGF-?1 is considered responsible for the initiation, development and persistence of fibrosis. In the present study, we investigated in vivo the therapeutic effect of the compound of white peony root oral liquids (cWPROL) on reducing the toxicity via modulating the expression levels of EGF and TGF-?1. Adult male Wistar rats were treated and tissue sections were obtained. The tissue sections were stained using histological, Masson and immunohistochemical staining. The results revealed that cWPROL had a higher rate of repairing damaged structures compared with the control group. In addition, immunohistochemistry showed that although cWPROL and the mixture of lidocaine, dexamethasone and gentamycin (mLDG) induced levels of EGF and TGF-?1 expression, there were differences between the two types of intervention. These results are significant for understanding that the mechanism of therapeutic effect of cWPROL varied to some extent from that of mLDG. PMID:24648940

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

    PubMed

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

    2013-09-01

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

  15. Spectrophotometric estimation of individual flavone glycosides in three Euphorbia species.

    PubMed

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

    1975-06-01

    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

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

    PubMed

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

    2014-01-01

    A new phenolic glycoside (1), named methyl 2-phenylpropanoate-2-O-?-D-apiofuranosyl-(1?6)-O-?-D-glucopyranoside, was isolated from the barks of Cinnamomum cassia, along with three known phenolic glycosides and four known lignan glycosides. The structure of 1 was elucidated by extensive interpretation of spectroscopic data and chemical method. Selected compounds were evaluated for their immunosuppressive activities against murine lymphocytes. Compounds 1, 2, 6 and 8 exhibited differential inhibition against ConA-induced T cells proliferation. PMID:25365297

  17. Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera

    Microsoft Academic Search

    Vakhtang Mshvildadze; Jean Legault; Serge Lavoie; Charles Gauthier; André Pichette

    2007-01-01

    Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides (1–4), a diarylheptanoid (5), a lignan (6), flavonoids (7–8) and chavicol glycosides (9–10). Among them, the diarylheptanoid glycoside, (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-?-l-arabinofuranosyl-(1?6)-?-d-glucopyranoside, papyriferoside A (1), was isolated and its structure was determined on the basis of 1D and

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

    PubMed

    Yamauchi, T; Abe, F

    1990-03-01

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

  19. Acylated phenolic glycosides from Solenostemma argel.

    PubMed

    Kamel, M S

    2003-04-01

    From the aerial parts of Solenostemma argel, four new acylated phenolic glycosides sinapyl alcohol 9-O-feruloyl-4-O-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin I (1), sinapyl alcohol 9-O-caffeoyl-4-O-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin II (2), sinapyl alcohol 9-O-feruloyl-4-O-alpha-rhamnopyranosyl-(1-->2)-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin III (3) and sinapyl alcohol 9-O-caffeoyl-4-O-alpha-rhamnopyranosyl-(1-->2)-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin IV (4) have been isolated. The structures of the isolated compounds were verified by means of MS and NMR spectral analyses. PMID:12648546

  20. New steroidal glycosides from Tribulus terrestris L.

    PubMed

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

    2012-01-01

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

  1. A new lathyrane diterpene glycoside from Euphorbia helioscopia L

    Microsoft Academic Search

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

    2010-01-01

    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.

  2. A new aryl glycoside from Euphorbia helioscopia L

    Microsoft Academic Search

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

    2009-01-01

    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.

  3. A novel flavone glycoside from the stem of Bauhinia purpurea.

    PubMed

    Yadava, R N; Tripathi, P

    2000-02-01

    A novel flavone glycoside, 5,6-dihydroxy-7-methoxyflavone 6-O-beta-D-xylopyranoside (1) was isolated from the chloroform-soluble fraction of the ethanolic extract of Bauhinia purpurea stems. PMID:11449482

  4. Flavonol glycosides from the flowers of Bellis perennis.

    PubMed

    Gudej, J; Nazaruk, J

    2001-11-01

    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

  5. Flavonol glycosides from the flowers of Bellis perennis

    Microsoft Academic Search

    J Gudej; J Nazaruk

    2001-01-01

    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.

  6. New phenylpropanoid glycosides from Juniperus communis var. depressa.

    PubMed

    Iida, Naoki; Inatomi, Yuka; Murata, Hiroko; Murata, Jin; Lang, Frank A; Tanaka, Toshiyuki; Nakanishi, Tsutomu; Inada, Akira

    2010-05-01

    Two new phenylpropanoid glycosides were isolated from the leaves and stems of Juniperus communis var. depressa (Cupressaceae) along with 14 known compounds. Their structures were determined by spectral analyses, in particular by 2D-NMR spectral evidence. PMID:20460808

  7. Three New Steroidal Glycosides from the Roots of Cynanchum stauntonii

    PubMed Central

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

    2013-01-01

    Three new steroidal glycosides, named as stauntosides L, M, and N (1–3), along with one known C21 steroidal glycoside, anhydrohirundigenin monothevetoside (4), were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR, HRESI-MS, and chemical methods. PMID:23555098

  8. Furostanol glycosides from the rhizomes of Helleborus orientalis.

    PubMed

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

    2010-10-01

    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

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

    PubMed Central

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

    2012-01-01

    Background Tree peonies are great ornamental plants associated with a rich ethnobotanical history in Chinese culture and have recently been used as an evolutionary model. The Qinling Mountains represent a significant geographic barrier in Asia, dividing mainland China into northern (temperate) and southern (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

  10. Adrenergic influence of uterine muscle contractions stimulated by a glycoside from the root of Dalbergia saxatilis.

    PubMed

    Uchendu, C N; Leek, B F

    1999-04-01

    The mechanism of uterine muscle contraction stimulated by a triterpenoid glycoside (dalsaxin) isolated from the root of D. saxatilis was investigated by in vitro methods in the rat. Dalsaxin caused a dose-related increase in uterine muscle contraction. The contraction was single and transient and was abolished by moderate doses of isoprenaline (1.80 nmol-0.40 mumol) and salbutamol (0.13-25 mumol). Adrenaline (9.10 nmol) also caused a reversible decrease (92.6%; P < 0.01) in myometrial contraction stimulated by this glycoside (0.24 mg/ml). Uterine muscle responses to dalsaxin (0.24 mg/ml) were enhanced by the beta-adrenergic receptor antagonist, propranolol, in a dose related manner. Atipamezole (1.50 ng/ml) but not prazosin (7.72 nmol-15.60 nmol) substantially reduced (80%; P < 0.01) myometrial contractions induced by this uterine spasmogen. The results suggest that dalsaxin enhances uterine muscle contraction by stimulating post junctional alpha 2-adrenergic receptors, presumably by inhibiting plasma membrane adenylate cyclase system and its associated increase in intracellular cAMP content. PMID:10641170

  11. Cytotoxic Flavonoid Glycosides from Rapistrum rugosum L.

    PubMed

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

    2012-01-01

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

  12. Four new glycosides from Pleurospermum franchetianum.

    PubMed

    Luo, Ying-Gang; Li, Bo-Gang; Zhang, Guo-Lin

    2002-06-01

    Four new glycosides, pleurofranosides I-IV, together with eight known compounds were isolated from the whole plants of Pleurospermum franchetianum Hemsl. Based on the spectral data and chemical evidence, the structures of pleurofranosides 1, II, III and IV were elucidated to be 16beta, 21beta, 23, 28-tetrahydroxyolean-12-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside, 13beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-fucopyranoside, 13beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-fucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside and 12beta, 28-epoxy-16beta, 23-dihydroxyolean-11-ene-3beta-yl-O-beta-D-glucopyranosyl-(1 --> 3)-[beta-D-glucopyranosyl-(1 --> 2)]-beta-D-glucopyranoside. The known compounds identified were octadecyl caprate, beta-sitosterol, (22E, 20S, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3-beta-ol, daucosterol, alpha-spinasterol-3-O-beta-D-glucopyranoside, quercetin-3, 7-di-O-beta-D-glucopyranoside, kaempferol-3, 7-di-O-alpha-L-rhamnopyranoside and kaempferol-3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside, respectively. PMID:12067162

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

    PubMed

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

    2013-10-01

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

  14. Neuromuscular blocking activity of a glycosidic extract of the plant Sarcolobus globosus.

    PubMed

    Mustafa, M R; Hadi, A H

    1990-01-01

    Crude glycoside extracts from the plant, Sarcolobus globosus, were tested on the rat phrenic nerve-diaphragm, chick biventer cervicis and frog rectus abdominis preparations. Nerve-stimulated twitches were inhibited by the extract. The muscle paralysis was not similar to that by curare-like blockers as it was not reversed by neostigmine or by a tetanus. Although contractures to acetylcholine or carbachol were not affected by 0.6 mg/ml of the extract, higher concentration of the extracts (3 mg/ml) depressed the log dose-response curve of acetylcholine and carbachol. The results suggest that the neuromuscular blocking effect of the extracts is either dose-dependent or due to a mixture of toxins with presynaptic or postsynaptic actions. PMID:2264070

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

  16. A new acylated flavonol glycoside from the leaves of Eriobotrya japonica.

    PubMed

    Kawahara, Nobuo; Satake, Motoyoshi; Goda, Yukihiro

    2002-12-01

    A new acylated flavonol glycoside was isolated from the leaves of Eriobotrya japonica along with two known flavonol glycosides. Their structures were determined by extensive spectroscopic investigation. PMID:12499604

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

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

    PubMed Central

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

    2012-01-01

    Phytosteryl glycosides occur in natural foods but little is known about their metabolism and bioactivity. Purified acylated steryl glycosides (ASG) were compared with phytosteryl esters (PSE) in mice. Animals on a phytosterol-free diet received ASG or PSE by gavage in purified soybean oil along with tracers cholesterol-d7 and sitostanol-d4. In a three-day fecal recovery study, ASG reduced cholesterol absorption efficiency by 45 ± 6% compared with 40 ± 6% observed with PSE. Four hours after gavage, plasma and liver cholesterol-d7 levels were reduced 86% or more when ASG was present. Liver total phytosterols were unchanged after ASG administration but were significantly increased after PSE. After ASG treatment both ASG and deacylated steryl glycosides (SG) were found in the gut mucosa and lumen. ASG was quantitatively recovered from stool samples as SG. These results demonstrate that ASG reduces cholesterol absorption in mice as efficiently as PSE while having little systemic absorption itself. Cleavage of the glycosidic linkage is not required for biological activity of ASG. Phytosteryl glycosides should be included in measurements of bioactive phytosterols. PMID:21538209

  19. Two new flavonol glycosides from Dimocarpus longan leaves.

    PubMed

    Xue, Yongmei; Wang, Wenjing; Liu, Yujiao; Zhan, Rui; Chen, Yegao

    2015-01-01

    From the extracts of Dimocarpus longan Lour leaves, 2 unusual flavonol glycosides, quercetin 3-O-(3?-O-2?-methyl-2?-hydroxylethyl)-?-D-xyloside (1) and quercetin 3-O-(3?-O-2?-methyl-2?-hydroxylethyl)-?-L-rhamnopyranoside (2), as well as 10 known compounds including 2 flavonol glycosides, afzelin (3) and kaempferol-3-O-?-L-rhamnopyranoside (4), 2 flavans, (-)-epicatechin (5) and proanthocyanidin A-2 (6), 3 triterpenoids, friedelin (7), epifriedelanol (8) and ?-amyrin (9), a peptide, N-benzoylphenylalanyl-N-benzoylphenylalaninate (10), and 2 sterols, ?-sitosterol (11) and daucosterol (12) were isolated and identified by using combination of mass spectrometry and various 1D and 2D NMR techniques. This is the first report of flavonoid glycosides possessing a 2-methyl-2-hydroxylethoxyl group in sugar moiety from D. longan. PMID:25325562

  20. Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera.

    PubMed

    Mshvildadze, Vakhtang; Legault, Jean; Lavoie, Serge; Gauthier, Charles; Pichette, André

    2007-10-01

    Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides (1-4), a diarylheptanoid (5), a lignan (6), flavonoids (7-8) and chavicol glycosides (9-10). Among them, the diarylheptanoid glycoside, (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside, papyriferoside A (1), was isolated and its structure was determined on the basis of 1D and 2D NMR, HPLC-MS, as well as high resolution mass spectroscopic data. Platyphylloside (4) exerted the strongest cytotoxic activity of all isolated compounds with IC(50) values ranging from 10.3 to 13.8 microM. PMID:17599372

  1. Kinetics of the alkaline hydrolysis of flavonoid glycosides

    Microsoft Academic Search

    M. D. Alaniya

    1977-01-01

    Summary  1. In a study of the kinetics of the alkaline hydrolysis of flavone glycosides it has been found that derivatives of 3,3?,4?,5,7-pentahydroxyflavone\\u000a hydrolyze faster than derivatives of 3,4?,5,7-tetrahydroxyflavone and of 3,4?,5,7-tetrahydroxy-3?-methoxyflavone.\\u000a \\u000a 2. In the hydrolysis of diglycosides of 3,3?,4?,5,7-pentahydroxyflavones the maximum amount of intermediate product is formed\\u000a after 2 min (3,4?,5,7-tetrahydroxyflavone glycoside), and in the case of 3,4?,5,7-tetrahydroxy-3?-methoxyflavone glycosides\\u000a after

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

    PubMed

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

    2015-04-01

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

  3. The identification of flavonoids as glycosides in human plasma.

    PubMed

    Paganga, G; Rice-Evans, C A

    1997-01-13

    This study describes evidence for the absorption of flavonoids and their presence in human plasma in the glycosylated form by HPLC analysis with photodiode array detection. Rutin and other quercetin glycosides, phloridzin, as well as an anthocyanin are detected simultaneously. In addition, a compound eluting with the spectral properties of the aurone family is identified. The results reveal that phloretin and quercetin are absorbed from the diet as glycosides. The polyphenols are detected in plasma from non-supplemented humans at individual levels in the range 0.5-1.6 microM. PMID:9003810

  4. New flavonol glycosides from the leaves of Caragana brachyantha.

    PubMed

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

    2015-01-01

    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

  5. A new biologically active flavonol glycoside from Psoralea corylifolia (Linn.).

    PubMed

    Yadava, R N; Verma, Vikash

    2005-08-01

    A new biologically active flavonol glycoside (1) mp 264-265 degrees C, C32H38O20, [M]+ 742 (EIMS) has been isolated from the methanol-soluble fraction of the defatted seeds of Psoralea corylifolia (Linn.). It was characterised as the new flavonol glycoside 3,5,3',4'-tetrahydroxy-7-methoxyflavone-3'-O-alpha-L-xylopyranosyl(1-->3)-O-alpha-L-arabinopyranosyl(1-->4)-O-beta-D-galactopyranoside by several colour reactions, spectral analysis and chemical degradations. Compound 1 showed anti-microbial activity against various bacteria and fungi. PMID:16087643

  6. Flavonoid glycosides of the black locust tree, Robinia pseudoacacia (Leguminosae)

    Microsoft Academic Search

    Nigel C. Veitch; Peter C. Elliott; Geoffrey C. Kite; Gwilym P. Lewis

    2010-01-01

    Four flavone glycosides isolated from extracts of the leaves of Robinia pseudoacacia (Leguminosae) were characterised by spectroscopic and chemical methods as the 7-O-?-d-glucuronopyranosyl-(1?2)[?-l-rhamnopyranosyl-(1?6)]-?-d-glucopyranosides of acacetin (5,7-dihydroxy-4?-methoxyflavone), apigenin (5,7,4?-trihydroxyflavone), diosmetin (5,7,3?-trihydroxy-4?-methoxyflavone) and luteolin (5,7,3?,4?-tetrahydroxyflavone). Assignment of glycosidic 1H and 13C resonances in their NMR spectra was facilitated by 2JHC correlations detected using the H2BC (heteronuclear two-bond correlation) pulse sequence. Spectroscopic analysis

  7. Five naphthalene glycosides from the roots of Rumex patientia

    Microsoft Academic Search

    Ömür Demirezer; Ay?e Kuruüzüm; Isabelle Bergere; H.-J Schiewe; Axel Zeeck

    2001-01-01

    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-?-d-glucopyranoside, 4,4?-binaphthalene-8,8?-O,O-di-?-d-glucopyranoside and 2-acetyl-3-methyl-1,8-dihydroxynaphthalene-8-O-?-d-glucopyranosyl (1?3) ?-d-glucopyranoside on the basis of spectral analysis. The other napthalene glycosides were determined as nepodin-8-O-?-d-glucopyranoside and torachrysone-8-O-?-d-glucopyranoside by comparison of their spectral data with those previously reported.

  8. Bufadienolide and spirostanol glycosides from the rhizomes of helleborusorientalis.

    PubMed

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

    2003-02-01

    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

  9. Caucasicosides E-M, furostanol glycosides from Helleborus caucasicus.

    PubMed

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

    2011-12-01

    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

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

    Microsoft Academic Search

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

    2010-01-01

    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

  11. 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.

  12. Biochemistry and Toxicology of the Diterpenoid Glycoside Atractyloside

    Microsoft Academic Search

    D. K Obatomi; P. H Bach

    1998-01-01

    Atractyloside (Atr) is a diterpenoid glycoside that occurs naturally in plants (many of which are used in ethnomedicines) found in Europe, Africa, South America, Asia and the far East. It is also present in animal grazing forage. Atr (and its analogues) may be present at levels as high as 600mg\\/kg dried plant material. Consumption of the plants containing Atr or

  13. A characteristic CH band in VCD of methyl glycosidic carbohydrates

    Microsoft Academic Search

    Tohru Taniguchi; Kenji Monde; Nobuaki Miura; Shin-Ichiro Nishimura

    2004-01-01

    Novel vibrational circular dichroism (VCD) studies in the CH region of a series of methyl glycosidic carbohydrates were examined. The specific CH stretching VCD band predicts absolute stereochemistries of their anomeric positions. The C-1 chiral information was extracted to the methoxy substituent as a probe. The concept of the vibrational chirality probe from a single chiral center in the presence

  14. On the differences between ouabain and digitalis glycosides.

    PubMed

    Fuerstenwerth, Hauke

    2014-01-01

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

  15. Pharmacokinetics and Bioavailability of Quercetin Glycosides in Humans

    Microsoft Academic Search

    Eva U. Graefe; Joerg Wittig; Silke Mueller; Anne-Kathrin Riethling; Bernhard Uehleke; Bernd Drewelow; Holger Pforte; Gisela Jacobasch; Hartmut Derendorf; Markus Veit

    2001-01-01

    Due to its potentially beneficial impact on human health, the polyphenol quercetin has come into the focus of medicinal interest. However, data on the bioavailability of quercetin after oral intake are scarce and contradictory. Previous investigations indicate that the disposition of quercetin may depend on the sugar moiety of the glycoside or the plant matrix. To determine the influence of

  16. The identification of flavonoids as glycosides in human plasma

    Microsoft Academic Search

    George Paganga; Catherine A Rice-Evans

    1997-01-01

    This study describes evidence for the absorption of flavonoids and their presence in human plasma in the glycosylated form by HPLC analysis with photodiode array detection. Rutin and other quercetin glycosides, phloridzin, as well as an anthocyanin are detected simultaneously. In addition, a compound eluting with the spectral properties of the aurone family is identified. The results reveal that phloretin

  17. Two new flavanone glycosides from Veratrum nigrum L.

    PubMed

    Li, Hui-Liang; Tang, Jian; Liu, Run-Hui; Zhang, Chuan; Zhang, Wei-Dong

    2009-01-01

    Two new flavanone glycosides have been isolated from the water soluble part of Veratrum nigrum L., belonging to the family Lilica. The structures of 3',4'-dimethoxyl-quercitrin and 4'-methoxyl-glucotricin have been established with the aid of extensive NMR spectroscopic studies. PMID:19173120

  18. Two new flavanone glycosides from Veratrum nigrum L

    Microsoft Academic Search

    Hui-Liang Li; Jian Tang; Run-Hui Liu; Chuan Zhang; Wei-Dong Zhang

    2009-01-01

    Two new flavanone glycosides have been isolated from the water soluble part of Veratrum nigrum L., belonging to the family Lilica. The structures of 3?,4?-dimethoxyl-quercitrin and 4?-methoxyl-glucotricin have been established with the aid of extensive NMR spectroscopic studies.

  19. Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis

    Microsoft Academic Search

    David HG Crout; Gabin Vic

    1998-01-01

    Remarkable advances in glycobiology in recent years have stimulated a resurgence of interest in carbohydrate chemistry. The challenge of producing the complex glycosides and oligosaccharides needed for research in glycobiology has led to the development of enzymatic methods that are now firmly established as part of the synthetic repertoire of the carbohydrate chemist.

  20. New flavone and isoflavone glycoside from Belamcanda chinensis

    Microsoft Academic Search

    Li Jin; Hai Sheng Chen; Zhao Bao Xiang; Shuang Liang; Yong Sheng Jin; Jian Guo Liu

    2007-01-01

    The new flavone, 5,4?-dihydroxy-6,7-methylenedioxy-3?-methoxyflavone, and one new isoflavone glycoside, 3?,5?-dimethoxy irisolone-4?-O-?-d-glucoside were isolated from the rhizomes of Belamcanda chinensis. Their structures were established based on the spectroscopic methods.

  1. Steroidal glycosides from the aerial part of Asclepias incarnata

    Microsoft Academic Search

    Tsutomu Warashina; Tadataka Noro

    2000-01-01

    The aerial part of Asclepias incarnata afforded 34 pregnane glycosides. These were confirmed to have lineolon, isolineolon, ikemagenin, 12-O-nicotinoyllineolon, deacylmetaplexigenin, metaplexigenin, rostratamine, 12-O-acetyllineolon, 15?-hydroxylineolon and 15?-hydroxyisolineolon moieties as their aglycones, and 2,6-dideoxyhexopyranose, glucopyranose and allopyranose as the corresponding sugar constituents. Their structures were determined using both spectroscopic and chemical methods.

  2. Apigenin glycosides from the flowers of Bellis perennis L.

    PubMed

    Nazaruk, J; Gudej, J

    2000-01-01

    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

  3. Marruboside, a New Phenylethanoid Glycoside from Marrubium Vulgare L

    Microsoft Academic Search

    Sevser Sahpaz; Thierry Hennebelle; François Bailleul

    2002-01-01

    A new phenylethanoid glycoside, marruboside, has been isolated from the aerial parts of Marrubium vulgare L. Its structure was established as 3,4-dihydroxy- g -phenylethoxy- O- [ g - d -apiofuranosyl-(1 M 2)- f - l -rhamnopyranosyl-(1 M 3)]-[ g - d -apiofuranosyl-(1 M 6)]-4- O -caffeoyl- g - d -glucopyranoside, on the basis of spectroscopic evidence.

  4. Marruboside, a new phenylethanoid glycoside from Marrubium vulgare L.

    PubMed

    Sahpaz, Sevser; Hennebelle, Thierry; Bailleul, François

    2002-06-01

    A new phenylethanoid glycoside, marruboside, has been isolated from the aerial parts of Marrubium vulgare L. Its structure was established as 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-apiofuranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)]-[beta-D-apiofuranosyl-(1-->6)]-4-O-caffeoyl-beta-D-glucopyranoside, on the basis of spectroscopic evidence. PMID:12049220

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

    PubMed

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

    2007-11-01

    In order to study the influence of sugar moiety, aglycon structure and microflora concentration on the human ileal hydrolysis of phenol glycosides, various quercetin and p-nitrophenol glycosides were incubated under anaerobic conditions (37 degrees C for 0, 0.5, 1, 2, 4, 6, 8, 10 and 24 h) with ileostomy fluids from three different donors. The glycosides, i.e. beta-D-glucopyranosides, beta-D-galactopyranosides, alpha-L-arabinofuranosides, beta-D-xylopyranosides and alpha-L-rhamnopyranosides as well as the liberated aglycones were identified by HPLC-DAD and HPLC-ESI-MS/MS. Among the quercetin glycosides under study, the 3-O-beta-D-glucopyranoside showed with 0.22 micromol/h the highest hydrolysis rate, followed by the 3-O-beta-D-galactopyranoside, the 3-O-beta-D-xylopyranoside and the 3-O-alpha-L-arabinofuranoside (0.04 and each 0.03 micromol/h, respectively). Quercetin 3-O-alpha-L-rhamnopyranoside was found to be stable for the entire incubation period. Using quercetin 3-O-beta-D-glucopyranoside as a representative example, linear hydrolysis rate was observed from 75 to 2500 microL ileostomy fluid corresponding to its microflora content (log 0.68 up to 21.9 colony forming units). Studies performed in the presence of antibiotics did not reveal any hydrolysis. The p-nitrophenol glycosides were hydrolyzed faster than the corresponding quercetin glycosides. The hydrolysis rate decreased from the beta-D-glucopyranoside (0.41 micromol/h), to the beta-D-galactopyranoside (0.21 micromol/h), the beta-D-xylopyranoside (0.12 micromol/h), the alpha-L-arabinofuranoside (0.09 micromol/h) to the alpha-L-rhamnopyranoside (0.06 micromol/h). These results demonstrate that the human ileal hydrolysis of phenol glycosides depends on the sugar and the aglycon structure as well as the microflora. PMID:17966139

  6. Warfarin reversal

    PubMed Central

    Hanley, J P

    2004-01-01

    Warfarin is the most commonly used oral anticoagulant in the UK. It is associated with few side effects apart from haemorrhage. The most appropriate way to reverse the anticoagulant effect of warfarin depends on the clinical circumstances. In serious bleeding, rapid reversal is required, whereas in minor bleeding or asymptomatic over anticoagulation, a more leisurely approach is usually appropriate. This review discusses the current approaches to warfarin reversal in clinical practice. The development of a uniform approach to warfarin reversal in the Northern Region is described. PMID:15509671

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

    PubMed

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

    2015-06-01

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

  8. Isoflavanones and their O-glycosides from Desmodium styracifolium.

    PubMed

    Zhao, Ming; Duan, Jin-Ao; Che, Chun-Tao

    2007-05-01

    Two isoflavanones (5,7-dihydroxy-2',3',4'-trimethoxy-isoflavanone and 5,7-dihydroxy-2'-methoxy-3',4'-methylenedioxy-isoflavanone), four isoflavanone O-glycosides (5,7-dihydroxy-2',3',4'-trimethoxy-isoflavanone 7-O-beta-glucopyranoside, 5,7-dihydroxy-2'-methoxy-3',4'-methylenedioxy-isoflavanone 7-O-beta-glucopyranoside, 5,7-dihydroxy-2',4'-dimethoxy-isoflavanone 7-O-beta-glucopyranoside, and 5,7,4'-trihydroxy-2',3'-dimethoxy-isoflavanone 7-O-beta-glucopyranoside), and a coumaronochromone (3,5,7,4'-tetrahydroxy-coumaronochromone), along with 25 known compounds, were isolated from the aerial parts of Desmodium styracifolium. This is for the first time isoflavanone O-glycosides were isolated from a natural source. PMID:17434190

  9. Triterpene glycosides from sea cucumber Stichopus japonicus Selenka.

    PubMed

    Maltsev, I I; Stonik, V A; Kalinovsky, A I; Elyakov, G B

    1984-01-01

    Triterpenoidal oligoglycosides from the far eastern sea cucumber Stitchopus japonicus Selenka collected in the Posiet Bay, Japan Sea were investigated. The glycoside fraction was shown to consist of two main components, holotoxins A1 and B1 which have been isolated by chromatography on silica gel columns. The chemical structures of the holotoxins were elucidated on the basis of chemical and physiochemical evidence (for formula see text). The proposed structures were compared with close related but not identical structures of holotoxin A and B from other collection of the same holothurian. The probable reasons of the distinction were discussed. The previously-established difference in glycoside structures between Stichopus japonicus and other representatives of the family Stichopodidae was corroborated. PMID:6467906

  10. Five naphthalene glycosides from the roots of Rumex patientia.

    PubMed

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

    2001-02-01

    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

  11. Two new monoterpenoid glycosides from Mentha spicata L

    Microsoft Academic Search

    Jian Zheng; Li-Jun Wu; Lu Zheng; Bin Wu; Ai-Hua Song

    2003-01-01

    Two new monoterpenoid glycosides, spicatoside A and spicatoside B, were isolated from the whole herbs of Mentha spicata L. which have anti-inflammatory and hemostatic activities. Their structures have been determined on the basis of spectral and chemical analysis. They are (+)-5-[1-(g -D-glucopyranosyloxymethyl)ethenyl]-2-methyl-2-cyclohexen-1-one (1), and (m )-5-{[2-( g -D-glucopyranosyloxy)-1-hydroxy-1-methyl]ethyl}-2-methyl-2-cyclohexen-1-one (2).

  12. Cyanidin glycosides in flowers of genus Corydalis (Fumariaceae)

    Microsoft Academic Search

    Fumi Tatsuzawa; Yuki Mikanagi; Norio Saito; Koichi Shinoda; Atsushi Shigihara; Toshio Honda

    2005-01-01

    Nine taxa of Corydalis were surveyed for their floral anthocyanins. Five cyanidin glycosides: cyanidin 3-glucoside, cyanidin 3-sambubioside, cyanidin 3-rutinoside, cyanidin 3-(2G-xylosylrutinoside) and cyanidin 3-(2G-xylosylrutinoside)-7-glucoside were isolated from these taxa and identified by chemical and spectroscopic techniques. A novel anthocyanin was found in the flowers of Corydalis elata and Corydalis flexuosa cultivars, and identified to be cyanidin 3-(2G-xylosylrutinoside)-7-glucoside. Two anthocyanins, cyanidin

  13. Hydrolysis of black soybean isoflavone glycosides by Bacillus subtilis natto

    Microsoft Academic Search

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

    2006-01-01

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

  14. A novel cytotoxic flavonoid glycoside from Physalis angulata

    Microsoft Academic Search

    N Ismail; M Alam

    2001-01-01

    A new flavonol glycoside, myricetin 3-O-neohesperidoside (1) was isolated from a cytotoxic MeOH extract of the leaves of Physalis angulata. Compound 1 showed remarkable cytotoxicity in vitro against murine leukemia cell line P-388, epidermoid carcinoma of the nasopharynx KB-16 cells, and lung adenocarcinoma A-549 with ED50 values of 0.048, 0.50 and 0.55 ?g ml?1, respectively.

  15. A new acylated quercetin glycoside from Ranunculus lanuginosus

    Microsoft Academic Search

    Josč Maria Prieto; Alessandra Braca; Ivano Morelli; Alison Barker; Urs Schaffner

    2004-01-01

    A new acylated quercetin glycoside, quercetin 3-O-(2-t-p-coumaroyl)-?-d-glucopyranosyl-(1?2)-?-d-glucopyranoside-7-O-?-d-glucopyranoside (1), together with the known 3-(3,4-dihydroxyphenyl)lactic acid (2) were isolated from Ranunculus lanuginosus leaves and identified on the basis of detailed spectral analysis, including 2D-NMR spectrometry and ESI-MS.

  16. Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina

    Microsoft Academic Search

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

    2009-01-01

    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

  17. A new acylated flavone glycoside from Colebrookea oppositifolia.

    PubMed

    Reddy, Ramireddy Venkata Narahari; Reddy, Bandi Anil Kumar; Gunasekar, Duvvuru

    2009-01-01

    A new acylated flavone glycoside, echioidinin 2'-O-beta-D-(2''-O-acetyl)glucopyranoside (1) along with the three known flavonoids, 5,6,7,8,5'-pentamethoxy-3',4'-methylenedioxyflavone (2), 5,2',6'-trihydroxy-7-methoxyflavone (3), and kaempferol 7,4'-dimethyl ether 3-O-beta-D-glucopyranoside (4), were isolated from the roots of Colebrookea oppositifolia. The structure of compound 1 was elucidated by extensive spectral and chemical studies. PMID:19219733

  18. A new acylated flavone glycoside from Colebrookea oppositifolia

    Microsoft Academic Search

    Ramireddy Venkata Narahari Reddy; Bandi Anil Kumar Reddy; Duvvuru Gunasekar

    2009-01-01

    A new acylated flavone glycoside, echioidinin 2?-O-?-d-(2?-O-acetyl)glucopyranoside (1) along with the three known flavonoids, 5,6,7,8,5?-pentamethoxy-3?,4?-methylenedioxyflavone (2), 5,2?,6?-trihydroxy-7-methoxyflavone (3), and kaempferol 7,4?-dimethyl ether 3-O-?-d-glucopyranoside (4), were isolated from the roots of Colebrookea oppositifolia. The structure of compound 1 was elucidated by extensive spectral and chemical studies.

  19. Flavone C-glycosides from flowers of Trollius ledebouri

    Microsoft Academic Search

    Jian-Hua Zou; Jun-Shan Yang; Yue-Sheng Dong; Liang Zhou; Geng Lin

    2005-01-01

    The ethanol extract of the flowers of Trollius ledebouri yielded four flavone C-glycosides, 2?-O-vanilloylvitexin, 2?-O-feruloylorientin, 2?-O-?-l-galactopyranosylvitexin, and 2?-O-?-l-galactopyranosylorientin, along with known compounds, 6?-O-acetylorientin, 2?-O-(4?-hydroxybenzoyl)vitexin, vitexin, and orientin. Their structures were elucidated by means of UV, IR, MS and NMR spectroscopic analyses.

  20. Phenylpropanoid glycosides from the leaves of Paulownia coreana

    Microsoft Academic Search

    Jin-Kyu Kim; Chuan-Ling SI; Young-Soo Bae

    2008-01-01

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

  1. New pregnane glycoside derivative from Caralluma retrospiciens (Ehrenb).

    PubMed

    Elsebai, Mahmoud Fahmi; Mohamed, Ietidal El-Tahir

    2015-08-01

    Retrospinoside (1) is a new polyoxy pregnane glycoside which was isolated and characterised from the aerial parts of Caralluma retrospiciens (Ehrenb.) N. E. Br., family Apocynaceae. The structure was established as 3-O-[?-D-glucopyranosyl-(1 ? 4)-?-D-(3-O-methyl-6-desoxygalactopyranosy)]-14,15,20-trihydroxy-4?-pregnane. Its structural elucidation was performed through extensive spectroscopic measurements including 1D- and 2D-NMR, and HRMS, in addition to chemical methods. PMID:25613301

  2. Steroidal glycosides from the aerial part of Asclepias incarnata.

    PubMed

    Warashina, T; Noro, T

    2000-02-01

    The aerial part of Asclepias incarnata afforded 34 pregnane glycosides. These were confirmed to have lineolon, isolineolon, ikemagenin, 12-O-nicotinoyllineolon, deacylmetaplexigenin, metaplexigenin, rostratamine, 12-O-acetyllineolon, 15beta-hydroxylineolon and 15beta-hydroxyisolineolon moieties as their aglycones, and 2.6-dideoxyhexopyranose, glucopyranose and allopyranose as the corresponding sugar constituents. Their structures were determined using both spectroscopic and chemical methods. PMID:10731028

  3. Ionone glycosides from the roots of Rehmannia glutinosa.

    PubMed

    Liu, Yan-Fei; Liang, Dong; Luo, Huan; Hao, Zhi-You; Wang, Yan; Zhang, Chun-Lei; Ni, Gang; Chen, Ruo-Yun; Yu, De-Quan

    2014-01-01

    Four new ionone and ionone glycosides (1-4), and a new monoterpene (5), together with 10 known analogues (6-15), were isolated from the air-dried roots of Rehmannia glutinosa. The structures of these compounds were elucidated on the basis of spectroscopic data analysis. Furthermore, in in vitro assays, compound 3 (10 ?M) exhibited moderate hepatoprotective activities against d-galactosamine-induced HL-7702 cell damage. PMID:24417558

  4. Neoconvalloside — A cardenolide glycoside from plants of the genus Convallaria

    Microsoft Academic Search

    N. F. Komissarenko; É. P. Stupakova

    1986-01-01

    In a study of the epigeal part and seeds ofConvallaria keiskei, C. majalis, andC. transcaucasica, in addition to lokundjoside, convalloside, convallotoxoloside, and neovallotoxoloside, we have isolated the previously unknown glycoside neoconvalloside, for which, on the basis of the physicochemical properties of the compound and of the products of its chemical transformations, the structure of strophanthidin 3-O-[O-ß-D-glucopyranosyl-(1 ? 2)-a-L-rhamnopyranoside has been

  5. Ent -kaurane diterpenoids and glycosides: Isolation, properties, and chemical transformations

    Microsoft Academic Search

    E. Kataev; R. N. Khaybullin; R. R. Sharipova; I. Yu. Strobykina

    2011-01-01

    This review is devoted to ent-kaurane diterpenoids and related glycosides, which represent two naturally occurring groups of compounds with interesting\\u000a structures and properties. Much useful information about the biogenesis and biological activities of these compounds is presented;\\u000a however, the greatest part of the review covers various aspects of the chemical transformations of native ent-kaurane diterpenoids, namely, their reactions via COOH,

  6. A new glycoside from the leaves of Neoalsomitra integrifoliola

    Microsoft Academic Search

    Dong Min Su; Jing Qu; You Cai Hu; Shi Shan Yu; Wen Zhao Tang; Yun Bao Liu; Shuang Gang Ma; De Quan Yu

    2008-01-01

    A new ionone glycoside (6R,9R)-blumenyl ?-l-rhamnopyranosyl-(1?6)-?-d-gluco-pyranoside (1), together with a new natural product 2-methoxyl-4-trans-propenyl-phenol ?-l-rhamnopyranosyl-(1?6)-?-d-glucopyranoside (2), was isolated from the leaves of Neoalsomitra integrifoliola. Their structures were elucidated by chemical and spectral analysis. Compound 1 showed weak anti-inflammatory and low-level antioxidant activities.

  7. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives

    PubMed Central

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

    2014-01-01

    A UDP glucosyltransferase from Bacillus licheniformis was overexpressed, purified, and incubated with nucleotide diphosphate (NDP) d- and l-sugars to produce glucose, galactose, 2-deoxyglucose, viosamine, rhamnose, and fucose sugar-conjugated resveratrol glycosides. Significantly higher (90%) bioconversion of resveratrol was achieved with ?-d-glucose as the sugar donor to produce four different glucosides of resveratrol: resveratrol 3-O-?-d-glucoside, resveratrol 4?-O-?-d-glucoside, resveratrol 3,5-O-?-d-diglucoside, and resveratrol 3,5,4?-O-?-d-triglucoside. The conversion rates and numbers of products formed were found to vary with the other NDP sugar donors. Resveratrol 3-O-?-d-2-deoxyglucoside and resveratrol 3,5-O-?-d-di-2-deoxyglucoside were found to be produced using TDP-2-deoxyglucose as a donor; however, the monoglycosides resveratrol 4?-O-?-d-galactoside, resveratrol 4?-O-?-d-viosaminoside, resveratrol 3-O-?-l-rhamnoside, and resveratrol 3-O-?-l-fucoside were produced from the respective sugar donors. Altogether, 10 diverse glycoside derivatives of the medically important resveratrol were generated, demonstrating the capacity of YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

  8. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives.

    PubMed

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

    2014-09-19

    A uridine diphosphate glucosyltransferase from Bacillus licheniformis was overexpressed, purified and incubated with nucleotide diphosphate (NDP) d- and l-sugars to produce glucose, galactose, 2-deoxyglucose, viosamine, rhamnose, and fucose sugar-conjugated resveratrol glycosides. A significantly higher (90%) bioconversion of resveratrol was achieved with ?d-glucose as the sugar donor to produce four different glucosides of resveratrol, resveratrol 3-O-?-d-glucoside, resveratrol 4?-O-?-d-glucoside, resveratrol 3,5-O-?-d-diglucoside, and resveratrol 3,5,4?-O-?-d-triglucoside. The conversion rates and number of products formed were found to vary with the other NDP-sugar donors. Resveratrol 3-O-?-d-2-deoxyglucoside, resveratrol 3,5-O-?-d-di-2-deoxyglucoside were found to be produced while using TDP-2-deoxyglucose as donor, however, monoglycosides resveratrol 4?-O-?-d-galactoside, resveratrol 4?-O-?-d-viosaminoside, resveratrol 3-O-?-l-rhamnoside, resveratrol 3-O-?-l-fucoside were produced from respective sugar donors. Altogether ten diverse glycoside derivatives of medicinally important resveratrol were generated; demonstrating the capacity for YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

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

    PubMed

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

    2014-05-23

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

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

    PubMed

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

    2015-06-26

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

  11. Reverse Logistics

    Microsoft Academic Search

    Chaihou Zhao; Weiming Liu; Bei Wang

    2008-01-01

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

  12. Cardenolide and oxypregnane glycosides from the root of Asclepias incarnata L.

    PubMed

    Warashina, T; Noro, T

    2000-04-01

    Twenty-nine new oxypregnane glycosides were obtained along with two known cardenolides, frugoside and gofruside, and three known 12-O-acylated pregnane glycosides from the roots of Asclepias incarnata L. (Asclepiadaceae). By detailed studies of the 1H- and 13C-NMR spectra, the structures were determined to be tri- to penta glycosides of isolineolon, 12-O-acetyllineolon, ikemagenin, 12-O-benzoylisolineolon, and two new 12-O-acylated pregnanes. PMID:10783071

  13. Saracoside: a new lignan glycoside from Saraca indica, a potential inhibitor of DNA topoisomerase IB.

    PubMed

    Mukherjee, Tulika; Chowdhury, Sayan; Kumar, Ashish; Majumder, Hemanta K; Jaisankar, Parasuraman; Mukhopadhyay, Sibabrata

    2012-06-01

    Chemical investigation of the stem bark of Saraca indica has resulted in the isolation of a new lignan glycoside, saracoside, along with four known lignan glycosides lyoniside, icariside E3, (+)5'-methoxyisolarciresinol-9'-O-beta-D-glucopyranoside and nudiposide, and a phenolic glucopyranoside, 3,4,5-trimethoxyphenyl-beta-D-glucopyranoside, which has been isolated for the first time from this species. The isolated lignan glycosides exhibit potent DNA topoisomerase IB inhibitory activity. PMID:22816303

  14. A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis.

    PubMed

    Nguelefack, Télesphore Benoît; Mbakam, Félicité Hermine Kamga; Tapondjou, Léon Azéfack; Watcho, Pierre; Nguelefack-Mbuyo, Elvine Pami; Ponou, Beaudelaire Kemvoufo; Kamanyi, Albert; Park, Hee-Juhn

    2011-04-01

    The aerial part of Rubus rigidus var. camerunensis (Rosaceae) is used to treat respiratory and cardiovascular disorders in the Cameroonian traditional medicine. The ethanol extract exhibited more potent antioxidant activity (E(max)s of 119% and 229% activity on DPPH and ?-carotene test) than aqueous extract. Bioactivity-guided fractionation of the ethanol extract based on free radical-scavenging assay (DPPH assay) afforded five flavonoid glycosides (four flavonol glycosides and an anthocyanin) and three glucosides of 19?-hydroxyursane-type triterpenoid (two monomeric and one dimeric triterpenoids). The flavonoids were identified as kaempferol 3-O-(2?-O-E-p-coumaroyl)-?-D-glucopyranoside (1), kaempferol-3-O-?-D-glucopyranoside (astragalin, 2), kaempferol-3-O-?-L-arabinofuranoside (juglanin, 3), quercetin-3-O-?-D-glucopyranoside (isoquercitrin, 4), pelargonidin-3-O-?-D-glucopyranoside (callistephin, 5). The three triterpenoids were 2?, 3?, 19?, 23-tetrahydroxyurs-12-ene-28-O-?-D-glucopyranosyl ester (nigaichigoside F(1), 6), 2?, 3?, 19?-trihydroxyurs-12-ene-23-carboxyl-28-O-?-D-glucopyranosyl ester (suavissimoside R(1), 7) as monomeric triterpenoids and coreanoside F(1) (8) as a dimeric triterpenoid. The flavonoids exhibited potent antioxidant activities (66 to 93.56% against DPPH radical) and they were also active on ?-carotene test. Coreanoside F(1) exhibited a 63% antioxidant activity, meanwhile the other two triterpenoids showed a weak activity. Three important facts on structure-activity relationship were observed: Compound 8, a dimeric triterpenoid glycoside, strongly enhanced antioxidant activity of its monomers, compound 3 with 3-O-?-L-arabinofuranyl has much more potent activity than compound 2 with 3-O-?-D-glucopyranosyl, and antocyanin (5) is more potent than its corresponding flavonol glycosides. PMID:21544719

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

    NASA Astrophysics Data System (ADS)

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

    2006-01-01

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

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

    PubMed Central

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

    2012-01-01

    Literature data about glycosides from sponges (Porifera, Demospongiae) are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed. PMID:23015769

  17. Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry.

    PubMed

    Aturki, Zeineb; Brandi, Valentina; Sinibaldi, Massimo

    2004-08-25

    The major flavanone-7-O-glycoside constituents in citrus fruit juices (naringin, hesperidin, neohesperidin, narirutin, and eriocitrin) were separated as diastereomers by multidimensional liquid chromatography. The method consisted of coupling two HPLC columns: a reversed-phase (RP(18)) column was used for the separation of flavanone glycosides, which were, then, individually switched into a carboxymethylated beta-cyclodextrin (beta-CD)-based column and resolved as the corresponding stereoisomers. The method was used for the full analysis of flavanone glycosides in fresh hand-squeezed and commercial fruit juices by combining the quantitative estimation with the diastereomeric analysis. Quantitative data were in general consistent with previously reported data in this field. CC-LC isomer analysis was carried out by coupling the beta-CD column with a mass spectrometer operated with negative ion electrospray ionization (ESI-MS). The results showed that hesperidin was present in orange juices almost exclusively as the 2S isomer, whereas narirutin had mainly the 2R configuration. In grapefruit juices (2S)-naringin prevailed with the respect to the 2R isomer, whereas the opposite was true for narirutin. Lemon juices contained eriocitrin stereoisomers in equal amount (50% each), but hesperidin was almost exclusively found as the 2S isomer. Significant differences of the diastereomeric ratios were observed between freshly squeezed juices and juices from commercial sources. PMID:15315361

  18. Reversible Sterilization

    ERIC Educational Resources Information Center

    Largey, Gale

    1977-01-01

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

  19. Flavonol glycosides in the petal of Rosa species as chemotaxonomic markers.

    PubMed

    Sarangowa, Ochir; Kanazawa, Tsutomu; Nishizawa, Makoto; Myoda, Takao; Bai, Changxi; Yamagishi, Takashi

    2014-11-01

    Thirteen flavonol glycosides were isolated from the petals of Rosa species belonging to the section Gallicanae, and their structures were identified from their spectroscopic data. These flavonol glycosides, along with two flavonol glycosides isolated from Rosa rugosa, in the petals of 31 Rosa species belonging to sections Gallicanae, Cinnamomeae, Caninae, and Synstylae were quantitatively analyzed by UPLC. The results indicated that the species belonging to these sections could be classified into four types (Type A, B, C and D) based on the pattern of flavonol glycoside contents, whereas the R. rugosa flavonol glycosides were detected only in section Cinnamomeae. A principal components analysis (PCA) calculated from the 15 flavonol glycosides contained in these samples supported the presence of four types. The distribution of the species in Type D (a group of Cinnamomeae) was shown to reflect close interrelationships, but species in Type B (one group of Gallicanae) could be subdivided into two groups, one of which contained species in section Synstylae. Moreover, the flavonol glycosides were grouped by sugar moieties: a disaccharide composed of two hexoses (S1), a hexose (S2), including a hexose with galloyl group, a pentose (S3), and a disaccharide composed of a hexose and a pentose (S4). The ratios of the amounts of S1-S4 to total flavonol glycoside content indicated that differences among the four sections were more distinctive than the amounts of the 15 flavonol glycosides. The 31 samples were divided into Type B, composed of one type of Gallicanae and Synstylae, Type A+C, composed of another type of Gallicanae and Caninae, and Type D, composed of Cinnamomeae. The R. rugosa flavonol glycosides were shown to be important chemotaxonomic markers for the classification of species in Cinnamomeae, and this method of using flavonol glycosides as chemotaxonomic markers could be useful for the identification of Rosa species belonging to sections Gallicanae, Cinnamomeae, Caninae, and Synstylae. PMID:25220498

  20. Reversible Cardiomyopathies

    PubMed Central

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

    2015-01-01

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

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

    PubMed

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

    2011-02-23

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

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

    PubMed

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

    2015-05-01

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

  3. A new flavonol glycoside from the Abelmoschus esculentus Linn.

    PubMed Central

    Liao, Haibing; Liu, Huixin; Yuan, Ke

    2012-01-01

    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

  4. Steroidal glycosides from the underground parts of Helleborus caucasicus.

    PubMed

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

    2008-03-01

    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

  5. Three new phenolic glycosides from Curculigo orchioides G.

    PubMed

    Zuo, Ai-Xue; Shen, Yong; Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhou, Jun; Lü, Jun; Chen, Ji-Jun

    2010-10-01

    Three new phenolic glycosides, curculigosides F-H (1-3), were isolated from rhizomes of Curculigo orchioides Gaertn. Their structures were elucidated based on comprehensive spectroscopic analyses including IR, MS, 1D- and 2D NMR (HSQC, COSY, and HMBC). Curculigosides F-H (1-3) were evaluated for their anti-HBV activity in vitro using the HBV transfected Hep G2.2.15 cell line. Compound 1 exhibited weak activity with an IC(50) value of 2.08 mM on hepatitis B virus (HBV) e antigen (HBeAg) secretion of the HepG2.2.15 cell line. PMID:20550957

  6. Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors.

    PubMed

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

    2011-04-01

    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

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

    PubMed

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

    2012-01-01

    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

  8. Amyloglucosidase-catalyzed synthesis of eugenyl and curcuminyl glycosides.

    PubMed

    Vijayakumar, Giriyapura R; Divakar, Soundar

    2007-04-01

    Glycosylation of the phenolic hydroxyl group of the phenyl propanoid systems, eugenol 1 and curcumin 2, using an amyloglucosidase from Rhizopus and a beta-glucosidase from sweet almonds together with carbohydrates (D-glucose 3, D-mannose 4, maltose 5, sucrose 6 and D-mannitol 7) in di-isopropyl ether produced glycosides at 7-52% yields in 72 h. Spectral studies indicated that the reaction occurred between the phenolic OH groups and C-1 and/or 6-O-groups of the carbohydrates with curcumin exhibiting bis glycosylation. PMID:17216300

  9. Flavonoid Glycosides from Arnica montana and Arnica chamissonis.

    PubMed

    Merfort, I; Wendisch, D

    1987-10-01

    Five flavonoid glycosides were identified from flowers of ARNICA MONTANA, four from A. CHAMISSONIS subsp. FOLIOSA var. INCANA. The structures were established on the basis of total acid hydrolysis and spectral data (UV, (1)H-NMR, (13)C-NMR, MS) as hispidulin 7- O-beta-glucoside, isorhamnetin 3- O-beta-glucoside, 3- O-beta- D-glucopyranosides of spinacetin, 6-methoxykaempferol and patuletin and querectin 3- O-(6''- O-acetyl)-beta- D-glucopyranoside. The latter compound can serve as distinctive marker between these two ARNICA species. The (1)H-NMR spectra in CD (3)OD are discussed. PMID:17269063

  10. A new steroidal glycoside from the seeds of Hyoscyamus niger.

    PubMed

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

    2013-01-01

    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

  11. New megastigmane glycoside and alkaloids from Streptomyces sp. YIM 63342.

    PubMed

    Yang, Xue-Qiong; Yang, Ya-Bin; Zhou, Hao; He, Guang-Wei; Zhao, Li-Xing; Xu, Li-Hua; Ding, Zhong-Tao

    2013-01-01

    New sesquiterpene glycoside, cyclodipeptide and piperidine derivative were isolated from Streptomyces sp. YIM 63342. On the basis of spectral data, their structures were determined as 3R, 5R, 6S, 7E, 9R-megastigman-7-en-3,5,6,9-tetrol-9-O-?-D-apiofuranosyl-(1??2)-?-D-glucopyranoside (1), cyclo (L-Pro-L-OMet) (2) and (R)-(E, E)-2-(l,3-pentadienyl) piperidine (3), together with three known compounds as N-acetyltyramine (4), lycoperodine-1 (5), cyclo(L-Pro-L-Tyr)(6). PMID:22934740

  12. New unusual pregnane glycosides with antiproliferative activity from Solenostemma argel.

    PubMed

    Plaza, Alberto; Perrone, Angela; Balestrieri, Maria Luisa; Felice, Francesca; Balestrieri, Ciro; Hamed, Arafa I; Pizza, Cosimo; Piacente, Sonia

    2005-08-01

    Seven new 15-keto pregnane glycosides, namely Stemmosides E--K, were isolated from Solenostemma argel. Stemmosides E--J are characterized by the occurrence of an uncommon 14 beta proton configuration while stemmosides E and F possess in addition a rare enolic function in C-16. On the other hand, stemmosides G-J display an unusual C-17 alpha side chain. Their structures were established by ESI-MS and NMR experiments. Moreover, the effect of these compounds on the VEGF-induced in Kaposi's sarcoma cell proliferation was tested. Results indicated that all the compounds reduced the cell proliferation in a dose dependent manner. PMID:15946718

  13. Megastigmane glycosides and an acylated triterpenoid from Eriobotrya japonica.

    PubMed

    Ito, H; Kobayashi, E; Li, S H; Hatano, T; Sugita, D; Kubo, N; Shimura, S; Itoh, Y; Yoshida, T

    2001-06-01

    Two new megastigmane glycosides, eriojaposides A (1) and B (2), and a new acylated triterpenoid (3) were isolated along with nine known compounds from a leaf extract of Eriobotrya japonica. The structures of 1--3 were characterized as (6R,9R)-3-oxo-alpha-ionyl-9-O-beta-xylopyranosyl-(1' '-->6')-beta-glucopyranoside, (6R,9R)-3-oxo-alpha-ionyl-9-O-alpha-rhamnopyranosyl-(1' '-->6')-beta-glucopyranoside, and 3 alpha-trans-feruloyloxy-2 alpha-hydroxyurs-12-en-28-oic acid, respectively, on the basis of spectral and chemical evidence. PMID:11421734

  14. Four new trace phenolic glycosides from Curculigo orchioides.

    PubMed

    Zuo, Ai-Xue; Shen, Yong; Zhang, Xue-Mei; Jiang, Zhi-Yong; Zhou, Jun; Lu, Jun; Chen, Ji-Jun

    2010-01-01

    Four new trace phenolic glycosides named orcinosides D (1), E (2), F (3), and G (4) were isolated from the rhizomes of Curculigo orchioides Gaertn. Based on comprehensive spectroscopic analyses including IR, FAB-MS, HR-ESI-MS, 1D- and 2D NMR (HSQC, HMBC), their structures were elucidated as orcinol-1-O-beta-D-xylopyranoside (1), orcinol-1-O-beta-D-apiofuranosyl-(1 --> 2)-beta-D-glucopyranoside (2), orcinol-3-O-beta-D-apiofuranosyl-1-O-beta-D-glucopyranoside (3), and 1-O-beta-D-glucopyranosyl-4-ethoxyl-3-hydroxymethylphenol (4). PMID:20390742

  15. Triterpene glycosides from Curculigo orchioides and their cytotoxic activity.

    PubMed

    Yokosuka, Akihito; Sato, Koji; Yamori, Takao; Mimaki, Yoshihiro

    2010-06-25

    Six new cycloartane glycosides (1-6) were isolated from the rhizomes of Curculigo orchioides. The structures of 1-6 were determined by spectroscopic analyses and the results of hydrolytic cleavage. Compounds 1-6, and their common aglycone (1a), were evaluated for cytotoxic activity against HL-60 human leukemia cells. Compounds 1 and 1a showed cytotoxic activity against HL-60 cells with IC(50) values of 9.0 and 1.8 microM, respectively. The cancer cell growth inhibition of 1a was also examined using a panel of 39 human cancer cell lines in the Japanese Foundation for Cancer Research. PMID:20524638

  16. HPLC Analysis of the Flavonoid Glycosides from Betulae folium.

    PubMed

    Dallenbach-Tölke, K; Nyirediy, S; Meier, B; Sticher, O

    1987-04-01

    The main flavonoid glycosides from BETULAE folium are separated with a RP-HPLC method. The mobile phase for the separation of the seven most important compounds (rutin, hyperin, quercetin-3-arabinofuranoside, quercetin-3-arabinopyranoside, quercetin-3-rhamnoside, quercetin-3-glucuronide, and myricetin-3-galactoside) was optimized with the "PRISMA" model, which is a multisolvent optimization system. The isocratic separations were finished within 30 minutes and the peak purity was controlled with diode-array detection. The method can be applied for quantitative determination, as was demonstrated for different samples of B. PENDULA and B. PUBESCENS. PMID:17268992

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

    Microsoft Academic Search

    G. G. E. Scudder; J. Meredith

    1982-01-01

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

  18. 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...

  19. Preserving leaves for tannin and phenolic glycoside analyses: A comparison of methods using three willow taxa

    Microsoft Academic Search

    Colin M. Orians

    1995-01-01

    Members of the Salicaceae often produce phenolic glycosides and condensed tannins. There is much debate on the best method for the preservation of leaf material prior to chemical analysis. Published results indicate freeze-drying, a method commonly used for tannin analysis, may be inappropriate for phenolic glycosides, unless done in a manner to prevent thawing during the drying process. Another commonly

  20. Inhibition of oxidation of omega-3 polyunsaturated fatty acids and fish oil by quercetin glycosides

    Microsoft Academic Search

    Gwendolyn M. Huber; H. P. Vasantha Rupasinghe; Fereidoon Shahidi

    2009-01-01

    The antioxidant properties of naturally occurring flavonols, quercetin glycosides, were examined and compared with common food antioxidants butylated hydroxytoluene (BHT) and ?-tocopherol. Antioxidants were incorporated into selected polyunsaturated fatty acids (PUFA) or fish oil in aqueous emulsions and bulk oil systems. The effectiveness of quercetin was similar to or greater than quercetin glycosides in inhibiting lipid oxidation in the oil-in-water

  1. Biochemical ecology of the forest tent caterpillar: responses to dietary protein and phenolic glycosides

    Microsoft Academic Search

    Richard L. Lindroth; Mark S. Bloomer

    1991-01-01

    Interactions between quaking aspen (Populus tremuloides) and the forest tent caterpillar (Malacosoma disstria) are likely to be influenced by leaf protein and phenolic glycoside levels, and insect detoxication activity. We investigated the direct and interactive effects of dietary protein and phenolic glycosides on larval performance and midgut enzyme activity of forest tent caterpillars. We conducted bioassays with six artificial diets,

  2. Enhanced Biotransformation Capacity of Rhodiola rosea Callus Cultures for Glycosid Production

    Microsoft Academic Search

    Zsuzsanna György; Ari Tolonen; Peter Neubauer; Anja Hohtola

    2005-01-01

    Rhodiola rosea is a promising medicinal plant that produces various glycosides. Recently we developed a successful method for cultivating it in liquid cultures of compact callus aggregates. In a previous study we reported the successful production of the glycosides of R. rosea by biotransformation of cinnamyl alcohol and tyrosol. In the present study we investigated the possibility of further increasing

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

    Microsoft Academic Search

    M. Deane Bowers; Nancy E. Stamp

    1997-01-01

    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

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

    Microsoft Academic Search

    R. L. Lindroth

    1989-01-01

    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

  5. A New Antibacterial Sesquiterpene Glycoside and Other Bioactive Compounds from Biebersteinia Heterostemon

    Microsoft Academic Search

    J. C. Meng; H. Lu; H. Li; L. Yang; R. X. Tan

    1999-01-01

    In addition to the plant sterols ?-sitosterol and daucosterol, a new bisabolane-typed sesquiterpene glycoside and three bioactive compounds (artemetin, geniposide and 6?-hydroxygeniposide) were characterized from the whole plant of Biebersteinia heterostemon endemic to the Tibetan area. The structure determination of the novel glycoside and identification of the known phytochemicals were accomplished by a combination of modern spectroscopic methods. Tests of

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

    PubMed

    Lampert, Evan C; Bowers, M Deane

    2010-10-01

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

  7. O-acylated flavonoid glycosides of the needles of Pinus sylvestris I. O-acetylated derivatives of flavonol glycosides

    Microsoft Academic Search

    G. G. Zapesochnaya; S. Z. Ivanova; S. A. Medvedeva; N. A. Tyukavkina

    1978-01-01

    Summary O-Acetylated flavonol glycosides have been isolated for the first time from the needles of the Scotch pine and the following structures have been established for them: 3,4'5,7-tetrahydroxy-3'-methoxyflavone 3-O-ß-D-(6?-O-acetylglucopyranoside), 3,4',5,7-tetrahydroxy-3'-methoxyflavone 3-O-ß-D-(6?-O-acetylgalactopyranoside), and 3,3',4',5,7-pentahydroxyflavone 3-O-ß-D-(6?-O-acetylglucopyranoside). The first two compounds have not previously been described in the literature.

  8. Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium.

    PubMed

    Calis, I; Kuruüzüm, A; Demirezer, L O; Sticher, O; Ganci, W; Rüedi, P

    1999-08-01

    (3R)-O-beta-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-beta-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[beta-D-glucopyranosyl-(1-->6)-glucopyranosyl]oxy-2'-hydroxy-3', 6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-beta-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-beta-D-galactopyranoside (5), quercetin-3-O-beta-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-beta-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2''-O-galloyl)-beta-D-glucopyranoside (8), and quercetin-3-O-beta-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays. PMID:10479312

  9. Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria

    PubMed Central

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

    2015-01-01

    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

  10. Identification of a novel flavonoid glycoside sulfotransferase in Arabidopsis thaliana

    PubMed Central

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

    2014-01-01

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

  11. Potent antiviral flavone glycosides from Ficus benjamina leaves.

    PubMed

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

    2012-03-01

    Crude ethanol extracts from Ficus benjamina leaves strongly inhibit Herpes Simplex Virus 1 and 2 (HSV-1/2) as well as Varicella Zoster Virus (VZV) cell infection in vitro. Bioassay-guided fractionation of the crude extract demonstrated that the most efficient inhibition of HSV-1 and HSV-2 was obtained with the flavonoid fraction. The present study was aimed to further isolate, purify and identify substances with potent antiviral activity from the flavonoid fraction of F. benjamina extracts. Flavonoids were collected from the leaf ethanol extracts through repeated purification procedure and HPLC analysis. The antiviral activity of each substance was then evaluated in cell culture. Three known flavone glycosides, (1) quercetin 3-O-rutinoside, (2) kaempferol 3-O-rutinoside and (3) kaempferol 3-O-robinobioside, showing highest antiviral efficiency were selected and their structure was determined by spectroscopic analyses including NMR and mass spectrometry (MS). These three flavones were highly effective against HSV-1 reaching a selectivity index (SI) of 266, 100 and 666 for compound 1, 2 and 3, respectively, while the SI of their aglycons, quercetin and kaempferol amounted only in 7.1 and 3.2, respectively. Kaempferol 3-O-robinobioside showed similar SI to that of acyclovir (ACV), the standard anti-HSV drug. Although highly effective against HSV-1 and HSV-2, these flavone glycosides did not show any significant activity against VZV. PMID:22155188

  12. Tissue factor inhibitory sesquiterpene glycoside from Eriobotrya japonica.

    PubMed

    Lee, Ming Hong; Son, Yeon Kyoung; Han, Yong Nam

    2004-06-01

    Tissue factor (TF, tissue thromboplastin) is a membrane bound glycoprotein, which accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor for activated factor VII (VIIa). The TF-factor VIIa complex (TF/VIIa) proteolytically activates factors IX and X, which leads to the generation of thrombin and fibrin clots. In order to isolate TF inhibitors, by means of a bioassay-directed chromatographic separation technique, from the leaves of Eriobotrya japonica Lindley (Rosaceae), a known sesquiterpene glycoside (2) and ferulic acid (3) were isolated as inhibitors that were evaluated using a single-clotting assay method for determining TF activity. Another sesquiterpene glycoside (1) was also isolated but was inactive in the assay system. Compound 3 was yielded by alkaline hydrolysis of compound 2. The structures of compounds 1, 2, and 3 were identified by means of spectral analysis as 3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranosyl nerolidol (1), 3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-(4-trans-feruloyl)-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranosyl nerolidol (2) and ferulic acid (3), respectively. Compounds 2 and 3 inhibited 50% of the TF activity at concentrations of 2 and 369 microM/TF units, respectively. PMID:15283463

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

    PubMed

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

    2013-01-01

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

  14. Reverse mortgages.

    PubMed

    Farnesi, D

    1995-09-01

    Elders and their families are often caught in a financial bind when it comes to paying for much-needed home care services. Reverse mortgages may offer a solution to elderly home care clients who own their homes but have a limited income with which to maintain their independence. PMID:10151233

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

    PubMed

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

    2001-01-01

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

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

    PubMed Central

    Guleria, Praveen; Yadav, Sudesh Kumar

    2013-01-01

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

  17. Two new cytotoxic triterpene glycosides from the sea cucumber Holothuria scabra.

    PubMed

    Han, Hua; Yi, Yanghua; Xu, Qiangzhi; La, Mingping; Zhang, Hongwei

    2009-12-01

    Two new triterpene glycosides, scabraside A (1) and B (2), and a structurally known compound (3), were isolated from the sea cucumber Holothuria scabra (Holothuriidae) collected from the South China Sea. Structure of these compounds was elucidated by spectroscopic and chemical methods. The glycosides 1 and 2 exhibit the same common structural features, i. e., the presence of 12- and 17-hydroxy groups in the holostane-type triterpene aglycone with a 9(11)-ene bond, but are different in the side chains of the triterpene aglycone. The glycosides 1 and 2 had significant in vitro cytotoxicity against four human tumor cell lines in comparison to 10-hydroxycamptothecin. PMID:19598081

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

    PubMed

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

    2014-05-01

    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

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

    PubMed

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

    2001-06-01

    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

  20. Hypoglycemic effects of sesquiterpene glycosides and polyhydroxylated triterpenoids of Eriobotrya japonica.

    PubMed

    De Tommasi, N; De Simone, F; Cirino, G; Cicala, C; Pizza, C

    1991-10-01

    The effects of the constituent sesquiterpene glycosides 1-3 and polyhydroxylated triterpenoids 5-6 isolated by MeOH extraction of Eriobotrya japonica were studied in genetically diabetic mice (C57BL/KS-db/db/Ola) and normoglycemic rats. The sesquiterpene glycoside 3 and the polyhydroxylated triterpenoids 5 and 6 produced a marked inhibition of glycosuria. Furthermore, 5 and 6 were able to reduce blood glucose levels in normoglycemic rats. While there are already some data reported on hypoglycemic activity of polyhydroxylated triterpenoids, there are no previous data showing hypoglycemic activity of sesquiterpene glycosides. PMID:1798792

  1. Variation in cardiac glycoside content of monarch butterflies from natural populations in eastern North America.

    PubMed

    Brower, L P; McEvoy, P B; Williamson, K L; Flannery, M A

    1972-08-01

    A new spectrophotometric assay has been used to determine the gross concentration of cardiac glycoside in individual monarch butterflies. Adults sampled during the fall migration in four areas of eastern North America exhibited a wide variation in cardiac glycoside concentration. The correlation between spectrophotometrically measured concentrations and emetic dose determinations supports the existence of a broad palatability spectrum in wild monarch butterflies. The cardiac gylcoside concentration is greater in females than in males and is independent of the dry weight of the butterflies; contrary to prediction, both the concentration mean and variance decrease southward. The defensive advantage of incorporating cardiac glycosides may be balanced by detrimental effects on individual viability. PMID:5043141

  2. 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.

  3. Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents.

    PubMed

    Liu, Ying-Guo; Li, Xiaxi; Xiong, De-Cai; Yu, Binhan; Pu, Xiaoping; Ye, Xin-Shan

    2015-05-01

    Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PC12 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PC12 cells in a dose-dependent manner. The anti-apoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure-activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia. PMID:25827400

  4. Antioxidant phenolic glycoside and flavonoids from Pieris japonica.

    PubMed

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

    2013-01-01

    A new phenolic glycoside, benzyl 2-hydroxy-4-O-?-D-glucopyranosyl-benzoate (1), along with nine known flavonoids, epicatechin-(2 ? O ? 7,4 ? 8)-ent-epicatechin (2), bis-8,8'-catechinylmethane (3), quercetin (4), quercetin-3-O-?-L-arabinfuranoside (5), quercetin-3-O-?-L-rhamnopyranoside (6), astilbin (7), engeletin (8), (2S,3R)-ent-catechin (9), and 2',4-dihydroxy-4'-methoxy-6'-O-?-D-glucopyranosyl dihydrochalcone (10), was isolated from the flowers of Pieris japonica. Their structures were elucidated on the basis of MS, 1D NMR, and 2D NMR techniques. This paper describes the isolation, structural elucidation as well as in vitro antioxidant activity of these compounds. PMID:23796053

  5. Pregnane-type steroidal glycosides from Gymnema griffithii Craib.

    PubMed

    Srisurichan, Suphongphan; Puthong, Songchan; Pornpakakul, Surachai

    2014-10-01

    Eight pregnane-type steroidal glycosides substituted with ortho-acetate groups were isolated from the methanolic extract of the pericarp of Gymnema griffithii fruits, and named gymnemogriffithosides A-H. Their structures were determined by spectroscopic analysis (one and two dimensional nuclear magnetic resonance, high resolution electrospray ionization mass spectrometry and attenuated total reflectance-Fourier transformed infrared spectroscopy), while the absolute structure of the steroidal skeleton of one of these was additionally determined using Mosher's method. All compounds were evaluated for their in vitro (i) cytotoxic effects against five human tumor cell lines (BT 474, Chago, Hep-G2, KATO-III and SW620) and (ii) ?-glucosidase inhibitory activity. PMID:25053002

  6. Novel flavonoid glycosides from the bulbs of Urginea indica Kunth.

    PubMed

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

    2010-07-01

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

  7. New Flavonoid Glycosides from Arnicae Flos DAB 91.

    PubMed

    Merfort, I; Wendisch, D

    1992-08-01

    Five flavonoid glycosides were identified from flowers of Arnica montana, ten from A. CHAMISSONIS subsp. FOLIOSA var. INCANA. The structures were established on the basis of acid hydrolysis and spectral data (UV, NMR, MS) as the 7-beta-glucosides of pectolinarigenin, apigenin, and chrysoeriol; luteolin 3'- O-beta-glucoside; the 3-beta-glucuronides of kaempferol, isorhamnetin, and 6-methoxykaempferol; the 3,7-di-beta-glucosides of quercetin and patuletin; the 3-beta-glucosides of betuletol and quercetagetin 6,3',4'-trimethyl ether; and the 7-[6''- O-(2-methylbutyryl)]=glucosides of luteolin and eupafolin. The latter four are new natural compounds. Differences between these two ARNICA species are discussed. PMID:17226484

  8. Deoxycholate-Based Glycosides (DCGs) for Membrane Protein Stabilisation.

    PubMed

    Bae, Hyoung Eun; Gotfryd, Kamil; Thomas, Jennifer; Hussain, Hazrat; Ehsan, Muhammad; Go, Juyeon; Loland, Claus J; Byrne, Bernadette; Chae, Pil Seok

    2015-07-01

    Detergents are an absolute requirement for studying the structure of membrane proteins. However, many conventional detergents fail to stabilise denaturation-sensitive membrane proteins, such as eukaryotic proteins and membrane protein complexes. New amphipathic agents with enhanced efficacy in stabilising membrane proteins will be helpful in overcoming the barriers to studying membrane protein structures. We have prepared a number of deoxycholate-based amphiphiles with carbohydrate head groups, designated deoxycholate-based glycosides (DCGs). These DCGs are the hydrophilic variants of previously reported deoxycholate-based N-oxides (DCAOs). Membrane proteins in these agents, particularly the branched diglucoside-bearing amphiphiles DCG-1 and DCG-2, displayed favourable behaviour compared to previously reported parent compounds (DCAOs) and conventional detergents (LDAO and DDM). Given their excellent properties, these agents should have significant potential for membrane protein studies. PMID:25953685

  9. New pregnane glycosides from Brucea javanica and their antifeedant activity.

    PubMed

    Chen, Yue-Yuan; Pan, Qiao-Dan; Li, Dian-Peng; Liu, Jin-Lei; Wen, Yong-Xin; Huang, Yong-Lin; Lu, Feng-Lai

    2011-03-01

    Three new pregnane glycosides, 3-O-?-D-glucopyranosyl-(1?2)-?-L-arabinopyranosyl-(20R)-pregn-5-ene-3?,20-diol (1), 3-O-?-L-arabinopyranosyl-(20R)-pregn-5-ene-3?,20-diol-20-O-?-D-glucopyranoside (2), 3-O-?-L-arabinopyranosyl-(20R)-pregn-5-ene-3?,20-diol-20-O-?-D-glucopyranosyl-(1?2)-?-D-glucopyranoside (3) were isolated along with four known compounds, 4-7, from the leaves and stems of Brucea javanica. Their structures were determined by detailed analyses of 1D- and 2D-NMR spectroscopic data. All of the compounds isolated from Brucea javanica were tested for the antifeedant activities against the larva of Pieris rapae. Compounds 1, 3, and 5 showed significant antifeedant activities after 72 h incubation. PMID:21404429

  10. Additional minor diterpene glycosides from Stevia rebaudiana Bertoni.

    PubMed

    Prakash, Indra; Chaturvedula, Venkata Sai Prakash

    2013-01-01

    Two additional novel minor diterpene glycosides were isolated from the commercial extract of the leaves of Stevia rebaudiana Bertoni. The structures of the new compounds were identified as 13-{?-D-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {?-D-xylopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)]-O-?-D-glucupyranosyl-ester} (1), and 13-{?-D-6-deoxy-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {?-D-glucopyranosyl-(1 ? 2)-O-[?-D-glucopyranosyl-(1 ? 3)-?-D-gluco-pyranosyl-ester} (2), on the basis of extensive 1D (1H- and 13C-) 2D NMR (COSY, HSQC and HMBC) and MS spectroscopic data as well as chemical studies. PMID:24184820

  11. A new steroid glycoside and furochromones from Cyperus rotundus L.

    PubMed

    Sayed, Hanaa M; Mohamed, Mahmoud H; Farag, Salwa F; Mohamed, Gamal A; Proksch, Peter

    2007-04-01

    Further phytochemical investigation of the aerial parts of Cyperus rotundus L. afforded a new steroid glycoside named sitosteryl (6'-hentriacontanoyl)-beta-D-galactopyranoside (4) in addition to three furochromones, khellin (2), visnagin (3) and ammiol (9). Furthermore, benzo-alpha-pyrone (coumarin) (1), salicylic acid (5), caffeic acid (6), protocatechuic acid (7), p-coumaric acid (8), tricin (10) and isorhamnetin (11) were isolated. The structures of these compounds were established by spectroscopic methods. The isolated furochromones were tested for insect antifeedant activity against larvae Spodoptera littoralis when incorporated in artificial diet and offered to larvae in a chronic feeding bioassay. Also, visnagin, khellin and sitosteryl (6'-hentriacontanoyl)-beta-D-galactopyranoside showed strong cytotoxic activity against L5178y mouse lymphoma cells and were also active in the brine shrimp lethality test. PMID:17479423

  12. Elucidation by Reverse Phase HPLC of Some Citrus Flavanones and Their Respective Dihydrochalcones: Structural Study

    Microsoft Academic Search

    J. A. Del Rio; J. Castillo; O. Benavente-Garcáa

    1994-01-01

    A high-performance liquid chromatographic method for the elucidation of the principal Citrus flavanone glycosides in biosynthesis and their respective dihydrochalcones has been developed. A C18 reverse phase column and an elution isocratic-gradient system is used with a mixture of water, acetonitrile and acetic acid. We describe the optimization process by studying the influence of the structural characteristics of these compounds

  13. Amphipaniculosides A-D, triterpenoid glycosides, and amphipaniculoside E, an aliphatic alcohol glycoside from the leaves of Amphilophium paniculatum.

    PubMed

    Samy, Mamdouh Nabil; Khalil, Hany Ezzat; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki; Kamel, Mohamed Salah

    2015-07-01

    Four new triterpenoids; One oleanane-, one ursane- and two cycloartane-type triterpenoids, named amphipaniculosides A-D, in addition to one new aliphatic alcohol glycoside, named amphipaniculoside E, were isolated from the 1-BuOH fraction of the leaves of Amphilophium paniculatum (L.) Kunth., together with five known compounds, (+)-lyoniresinol 3?-O-?-d-glucopyranoside, (-)-lyoniresinol 3?-O-?-d-glucopyranoside, acteoside (verbascoside), isoacteoside (isoverbascoside), and luteolin 7-O-?-d-glucopyranoside. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments ((1)H, (13)C, DEPT, COSY, ROESY, HSQC, HMBC) in combination with HR-ESI-MS and by comparisons of their physical and spectroscopic data with literature values. PMID:25804328

  14. Solubility Enhancement of Steviol Glycosides and Characterization of Their Inclusion Complexes with Gamma-Cyclodextrin

    PubMed Central

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

    2011-01-01

    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 13C 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

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

    Microsoft Academic Search

    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

    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.

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

    PubMed

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

    2010-09-01

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

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

    PubMed

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

    2011-01-01

    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

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

    PubMed Central

    Zheng, Fei

    2013-01-01

    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

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

    PubMed

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

    2015-06-01

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

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

    PubMed

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

    2012-11-01

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

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

    Microsoft Academic Search

    Magdalena Biesaga; Krystyna Pyrzynska

    2009-01-01

    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

  2. Content of quercetin glycosides and fructooligosaccharides in onion stored in a cold room

    Microsoft Academic Search

    Katarzyna Grzelak; Joanna Milala; Bogus?aw Król; Franciszek Adamicki; Ewa Bade?ek

    2009-01-01

    In the paper, the authors present the qualitative and quantitative composition of quercetin glycosides and fructooligosaccharides\\u000a (FOS) in onions commonly grown in Poland of the varieties: Napoleon, Sprinter and Grabowska from the 2006 and 2007 crops,\\u000a stored in a cold room under standard conditions from October until February. Quercetin glycosides and FOS have been determined\\u000a using the HPLC method. It

  3. Controlof PhenotypicExpressionof CulturedB16 MelanomaCells by Plant Glycosides1 OĂ\\

    Microsoft Academic Search

    Shizuo Odashima; Takahide Ohta; Hiroyuki Kohno; Takeshi Matsuda; Isao Kitagawa; Hiroko Abe; Shigeru Arichi

    The effects of two plant glycosides, ginsenosides Rh, and Rh2,on the growth and differentiation of mouse melanoma (B16) cells in culture were studied. These plant glycosides have a dammarane skeleton resembling a steroid skeleton as an agly- cone. Ginsenoside Rh2 inhibits the growth of B16 melanoma cells, causes morphological alterations, and stimulates melano- genesis at high cellular density. When ginsenoside

  4. Scutellarein 4?-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae)

    Microsoft Academic Search

    Renée J Grayer; Nigel C Veitch; Geoffrey C Kite; Alan J Paton; Philip J Garnock-Jones

    2002-01-01

    The flavonoid profiles of two monotypic genera, Teucridium and Tripora, have been studied by analytical methods. These genera were formerly placed in the Verbenaceae, but are now classified in the Lamiaceae, subfamily Ajugoideae. The major flavonoids of both genera were identified as glycosides of scutellarein 4?-methyl ether (5,6,7-trihydroxy-4?methoxyflavone) and acacetin (5,7-dihydroxy-4?-methoxyflavone). The new flavone glycoside, scutellarein 4?-methyl ether 7-O-rutinoside, was

  5. Steroidal glycosides from the aerial part of Asclepias incarnata L. II.

    PubMed

    Warashina, T; Noro, T

    2000-01-01

    Thirty new steroidal glycosides were obtained from the aerial part of Asclepias incarnata L. (Asclepiadaceae). These glycosides were confirmed to have lineolon, isolineolon, 12-O-acetyllineolon, 12-O-(Z)-cinnamoyllineolon, metaplexigenin, 15 beta-hydroxylineolon, 15 beta-hydroxyisolineolon, 16 alpha-hydroxyisolineolon, 12-O-tigloyl-16 alpha-hydroxyisolineolon as the aglycone and 2,6-dideoxyhexopyranose as the sugar sequence by spectroscopic methods and chemical evidence. PMID:10705484

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

    Microsoft Academic Search

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

    2006-01-01

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

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

    Microsoft Academic Search

    Nikolai Bondarev; Oxana Reshetnyak; Alexander Nosov

    2001-01-01

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

  8. HPLC Separation of Flavonoids and Flavonoid Glycosides Using a Polystyrene\\/Divinylbenzene Column

    Microsoft Academic Search

    Nirdosh K. Jagota; Steve F. Cheatham

    1992-01-01

    A polystyrene-divinylbenzene column was investigated for the separation of four different classes of flavonoids and flavonoid glycosides. These analytes were separated using either methanol-water or acetonitrile-water gradients. Acetonitrile-water gradients were judged to be superior for the overall separation of the four classes of flavonoids and flavonoid glycosides. Correlations between chemical structure, and retention and separability are discussed for the various

  9. Preserving leaves for tannin and phenolic glycoside analyses: A comparison of methods using three willow taxa.

    PubMed

    Orians, C M

    1995-09-01

    Members of the Salicaceae often produce phenolic glycosides and condensed tannins. There is much debate on the best method for the preservation of leaf material prior to chemical analysis. Published results indicate freeze-drying, a method commonly used for tannin analysis, may be inappropriate for phenolic glycosides, unless done in a manner to prevent thawing during the drying process. Another commonly employed method, air-drying, is appropriate for phenolic glycosides but inappropriate for condensed tannins. I present evidence using willow leaves that demonstrates that: (1) leaves freeze-dried in external flasks without temperature control contain lower concentrations of phenolic glycosides (salicortin and 2'-cinnamoylsalicortin), (2) air-dried leaves have reduced concentrations of condensed tannins, while (3) vacuum-dried fresh leaves have high concentrations of both phenolic glycosides and condensed tannins. Freeze-drying caused salicortin and 2'-cinnamoyl salicortin concentrations to drop by 20 mg/g and 4 mg/g, respectively. Salicin, a product of salicortin and 2'-cinnamoyl salicortin degradation, is absent in vacuum-dried leaves, present in air-dried leaves and very high in freeze-dried leaves. Thus, the presence of salicin in this system is an artifact of the preservation technique. Condensed tannin concentrations dropped nearly 20 mg/g when leaves were air-dried. Thus, vacuum-drying fresh leaves allows researchers to quantify phenolic glycosides and condensed tannins from the same leaf material. PMID:24234623

  10. Isolation, characterization, and surfactant properties of the major triterpenoid glycosides from unripe tomato fruits.

    PubMed

    Yamanaka, Takao; Vincken, Jean-Paul; de Waard, Pieter; Sanders, Mark; Takada, Norihisa; Gruppen, Harry

    2008-12-10

    Various triterpenoid glycosides were extracted from whole unripe tomato fruits ( Lycopersicon esculentum cv. Cedrico), using aqueous 70% (v/v) ethanol to study their surfactant properties. Cation-exchange chromatography using a Source 15S column and subsequent semipreparative HPLC using an XTerra RP18 were employed to purify individual triterpenoid glycosides from the extract. The structure of the purified compounds was established by mass spectrometry and nuclear magnetic resonance spectroscopy. The furostanol glycoside tomatoside A (749 mg/kg of DW) and the glycoalkaloids alpha-tomatine (196 mg/kg of DW) and esculeoside A (427 mg/kg of DW) were the major triterpenoid glycosides present. Furthermore, minor amounts of a new dehydrofurostanol glycoside, dehydrotomatoside, were found. The critical micelle concentrations of the major triterpenoid glycosides, alpha-tomatine, tomatoside A, and esculeoside A, were determined as 0.099, 0.144, and 0.412 g/L, respectively. The results show that tomatoside A, and not the more well-known alpha-tomatine, is the predominant triterpenoidal surfactant in unripe tomato fruits. PMID:18998702

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

    PubMed Central

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

    1980-01-01

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

  12. Reversible Computation and Reversible Programming Languages

    Microsoft Academic Search

    Tetsuo Yokoyama

    2010-01-01

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

  13. Triterpene glycosides from the tubers of Anemone coronaria.

    PubMed

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

    2009-07-01

    Six new triterpene glycosides (1-6), together with 11 known ones (7-17), have been isolated from a glycoside-enriched fraction prepared from the tubers of Anemone coronaria L. (Ranunculaceae). On the basis of extensive spectroscopic analysis, including 2D NMR data, and the results of hydrolytic cleavage, the structures of 1-6 were determined to be 3beta-[(O-beta-D-glucopyranosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-2beta,23-dihydroxyolean-12-en-28-oic acid (1), 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid (2), 3beta-[(O-beta-D-glucopyranosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (3), 3beta-[(O-beta-D-glucopyranosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-2beta,23-dihydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (4), 3beta-[(O-beta-D-glucopyranosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-2beta-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (5), and 3beta-[(O-beta-D-glucopyranosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-18-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (6), respectively. Furthermore, the isolated compounds were evaluated for their cytotoxic activity against HSC-2 cells. PMID:19571419

  14. CHARMM Additive All-Atom Force Field for Glycosidic Linkages between Hexopyranoses

    PubMed Central

    Guvench, Olgun; Hatcher, Elizabeth R.; Venable, Richard M.; Pastor, Richard W.; MacKerell, Alexander D.

    2009-01-01

    We present an extension of the CHARMM hexopyranose monosaccharide additive all-atom force field to enable modeling of glycosidic-linked hexopyranose polysaccharides. The new force field parameters encompass 1?1, 1?2, 1?3, 1?4, and 1?6 hexopyranose glycosidic linkages, as well as O-methylation at the C1 anomeric carbon, and are developed to be consistent with the CHARMM all-atom biomolecular force fields for proteins, nucleic acids, and lipids. The parameters are developed in a hierarchical fashion using model compounds containing the key atoms in the full carbohydrates, in particular O-methyl-tetrahydropyran and glycosidic-linked dimers consisting of two molecules of tetrahyropyran or one of tetrahydropyran and one of cyclohexane. Target data for parameter optimization include full two-dimensional energy surfaces defined by the ?/? glycosidic dihedral angles in the disaccharide analogs as determined by quantum mechanical MP2/cc-pVTZ single point energies on MP2/6-31G(d) optimized structures (MP2/cc-pVTZ//MP2/6-31G(d)). In order to achieve balanced, transferable dihedral parameters for the ?/? glycosidic dihedral angles, surfaces for all possible chiralities at the ring carbon atoms involved in the glycosidic linkages are considered, resulting in over 5000 MP2/cc-pVTZ//MP2/6-31G(d) conformational energies. Also included as target data are vibrational frequencies, pair interaction energies and distances with water molecules, and intramolecular geometries including distortion of the glycosidic valence angle as a function of the glycosidic dihedral angles. The model-compound optimized force field parameters are validated on full disaccharides through comparison of molecular dynamics results to available experimental data. Good agreement is achieved with experiment for a variety of properties including crystal cell parameters and intramolecular geometries, aqueous densities, and aqueous NMR coupling constants associated with the glycosidic linkage. The newly-developed parameters allow for the modeling of linear, branched, and cyclic hexopyranose glycosides both alone and in heterogenous systems including proteins, nucleic acids and/or lipids when combined with existing CHARMM biomolecular force fields. PMID:20161005

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

    PubMed

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

    2013-04-01

    A phytochemical analysis of the whole plant of Allium schoenoprasum, has led to the isolation of four spirostane-type glycosides (1-4), and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25S)-spirost-5-en-3?,12?,21-triol 3-O-?-L-rhamnopyranosyl-(1?2)-?-D-glucopyranoside (1), (20S,25S)-spirost-5-en-3?,11?,21-triol 3-O-?-L-rhamnopyranosyl-(1?2)-?-D-glucopyranoside (2), laxogenin 3-O-?-L-rhamnopyranosyl-(1?2)-[?-D-glucopyranosyl-(1?4)]-?-D-glucopyranoside (3), and (25R)-5?-spirostan-3?,11?-diol 3-O-?-D-glucopyranosyl-(1?3)-[?-D-glucopyranosyl-(1?4)]-?-D-galactopyranoside (4). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines. PMID:23357597

  16. Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina.

    PubMed

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

    2009-02-01

    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

  17. Antimicrobial and cytotoxic isopimarane diterpenoid glycosides from Microlepia pilosissima Ching.

    PubMed

    Hu, Jiang; Song, Yan; Li, Hui; Mao, Xia; Zhao, YongMao; Shi, Xiaodong

    2015-03-01

    A phytochemical investigation of the EtOH extract of the dry fronds of Microlepia pilosissima Ching afforded four new isopimarane diterpene glycosides, 3?-O-?-L-rhamnopyranosyl-7?-O-?-D-fucopyranosyl-ent-iospimara-8(14),15-diene (1), 3?-O-[2-O-acetyl-?-L-rhamnopyranosyl]-7?-O-?-D-fucopyranosyl-ent-iospimara-8(14),15-diene (2), 3?-O-[?-D-glucopyranosyl-(1?2)-?-L-rhamnopyranosyl]-7?-O-?-D-fucopyranosyl-ent-iospimara-8(14),15-diene (3) and 3?-O-[?-D-fucopyranosyl-(1?2)-?-L-rhamnopyranosyl]-7?-O-?-D-fucopyranosyl-ent-iospimara-8(14),15-diene (4) as well as their aglycone, 3?,7?-dihydroxy-ent-iospimara-8(14),15-diene (5). Their structures were characterized by spectroscopic methods, including 1D-NMR, 2D-NMR, and HR-ESI-MS. The isolated compounds were evaluated in vitro for antimicrobial properties against three pathogen fungi and two oral pathogens and cytotoxicities against eight tumor cell lines. As a result, compounds 1-4 appeared to be promising antimicrobial potential and possessed moderate cytotoxic activities against the tested tumor cell lines. PMID:25542683

  18. Extracellular Glycoside Hydrolase Activities in the Human Oral Cavity.

    PubMed

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

    2015-08-15

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

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

    PubMed

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

    2015-01-01

    The antibacterial and anti-inflammatory activities, and protective effects of extracts (flavonoid glycosides) of Polygonum capitatum were investigated to detect the evidence for the utilization of the herb in the clinical therapy of gastritis caused by H. pylori. A mouse gastritis model was established using H. pylori. According to treating methods, model mice were random assigned into a model group (MG group), a triple antibiotics group (TG group, clarithromycin, omeprazole and amoxicillin), low/middle/high concentrations of flavonoid glycosides groups (LF, MF and HF groups) and low/middle/high concentrations of flavonoid glycosides and amoxicillin groups (LFA, MFA and HFA groups). A group with pathogen-free mice was regarded as a control group (CG group). The eradicate rates of H. pylori were 100%, 93%, 89% in TG, MFA and HF groups. The serum levels of IFN-gamma and gastrin were higher in a MG group than those from all other groups (P < 0.05). The serum levels of IFN-gamma and gastrin were reduced significantly in LF, MF and HF groups (P < 0.05) while little changes were observed in LFA, MFA and HFA groups. In contrast, the serum levels of IL-4 were lower and higher in MG and CG groups compared with other groups (P<0.05). The serum levels of IL-4 were increased significantly in LF, MF and HF groups (P < 0.05) while little changes were found in LFA, MFA and HFA groups. According to pathological scores, flavonoid glycosides therapy showed better protection for gastric injuries than the combination of flavonoid glycoside and amoxicillin (P < 0.05). The results suggested that flavonoid glycoside has repairing functions for gastric injuries. The results suggest that the plant can treat gastritis and protect against gastric injuries. The flavonoid glycosides from Polygonum capitatum should be developed as a potential drug for the therapy of gastritis caused by H. pylori. PMID:25993258

  20. REVERSE ENGINEERING RECENT ADVANCES

    E-print Network

    Telea, Alexandru C.

    #12;REVERSE ENGINEERING ­ RECENT ADVANCES AND APPLICATIONS Edited by Alexandru C. Telea #12;Reverse;#12;Contents Preface IX Part 1 Software Reverse Engineering 1 Chapter 1 Software Reverse Engineering GUIsurfer: A Reverse Engineering Framework for User Interface Software 31 José Creissac Campos, Joăo Saraiva

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

    PubMed

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

    2010-11-22

    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

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

    PubMed Central

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

    2009-01-01

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

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

    PubMed

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

    2010-07-28

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

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

    SciTech Connect

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

    2011-08-01

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

  5. Characterization of Five ?-Glycoside Hydrolases from Cellulomonas fimi ATCC 484

    PubMed Central

    Gao, Juan

    2014-01-01

    The Gram-positive bacterium Cellulomonas fimi produces a large array of carbohydrate-active enzymes. Analysis of the collection of carbohydrate-active enzymes from the recent genome sequence of C. fimi ATCC 484 shows a large number of uncharacterized genes for glycoside hydrolase (GH) enzymes potentially involved in biomass utilization. To investigate the enzymatic activity of potential ?-glucosidases in C. fimi, genes encoding several GH3 enzymes and one GH1 enzyme were cloned and recombinant proteins were expressed in Escherichia coli. Biochemical analysis of these proteins revealed that the enzymes exhibited different substrate specificities for para-nitrophenol-linked substrates (pNP), disaccharides, and oligosaccharides. Celf_2726 encoded a bifunctional enzyme with ?-d-xylopyranosidase and ?-l-arabinofuranosidase activities, based on pNP-linked substrates (CfXyl3A). Celf_0140 encoded a ?-d-glucosidase with activity on ?-1,3- and ?-1,6-linked glucosyl disaccharides as well as pNP-?-Glc (CfBgl3A). Celf_0468 encoded a ?-d-glucosidase with hydrolysis of pNP-?-Glc and hydrolysis/transglycosylation activities only on ?-1,6-linked glucosyl disaccharide (CfBgl3B). Celf_3372 encoded a GH3 family member with broad aryl-?-d-glycosidase substrate specificity. Celf_2783 encoded the GH1 family member (CfBgl1), which was found to hydrolyze pNP-?-Glc/Fuc/Gal, as well as cellotetraose and cellopentaose. CfBgl1 also had good activity on ?-1,2- and ?-1,3-linked disaccharides but had only very weak activity on ?-1,4/6-linked glucose. PMID:25225266

  6. Optimization of a liquid chromatography method based on simultaneous electrospray ionization mass spectrometric and ultraviolet photodiode array detection for analysis of flavonoid glycosides.

    PubMed

    Cuyckens, Filip; Claeys, Magda

    2002-01-01

    Different reversed-phase liquid chromatography (LC) columns of conventional dimensions were coupled to an ultraviolet photodiode array detector (UV-DAD) and a magnetic sector-type spectrometer, equipped with an electrospray ionization (ESI) source, by a laboratory-made flow splitter. A mixture of three flavonoid-O-glycosides was employed to examine the effects of the solvent composition, the flow rate, the stationary phase, the pH and the organic acid added, on the chromatographic separation, the UV-DAD detection, the ESI process and the entire LC system with ESI-MS and UV-DAD detection. In the positive ion mode, methanol containing 1% acetic acid was by far the most sensitive in ESI-MS analysis, whereas an acetonitrile/water mobile phase containing 0.5% formic acid was proved to give the best sensitivity in LC/ESI-MS/UV-DAD analysis. In the negative ion mode, the highest sensitivity was obtained with a mobile phase containing 0.1% formic acid, while addition of bases decreased the sensititvity. The optimal flow rate was higher in negative ESI (20-50 micro L/min) than in positive ESI (5 micro L/min), and the percentage of organic phase had an influence on the sensitivity of ESI-MS detection. With regard to the selection of a suitable C(18) reversed-phase LC column, a column which is well end-capped is to be preferred, because residual silanol groups appear to impair the separation of flavonoid glycosides. The optimized LC/ESI-MS/UV-DAD method was applied to a commercial Crataegus extract, which is used in phytomedicine to treat cardiovascular problems and is known to be rich in flavonoids. It is demonstrated how UV spectra and first-order ESI mass spectra allow a fast characterization of flavonoids, even if reference compounds are not available or at hand. PMID:12478580

  7. The flavonol glycosides in the fruit of Pyrus communis L. cultivar Bon Chrétien

    PubMed Central

    Nortjé, B. K.; Koeppen, B. H.

    1965-01-01

    1. Two new flavonol glycosides were isolated from the fruit of Pyrus communis L. cultivar Bon Chrétien. These were identified as isorhamnetin 3-rhamnogalactoside and a derivative of isorhamnetin 3-glucoside which was associated (possibly acylated) with an unknown aliphatic organic acid. 2. The melting point of isorhamnetin 3-glucoside isolated from Bon Chrétien pears is different from that of isorhamnetin 3-glucoside previously isolated from Argemone mexicana and Calendula officinalis. 3. Isorhamnetin 3-rhamnoglucoside was isolated from the fruit of Pyrus communis L. cultivar Bon Chrétien. This glycoside appears to be identical with narcissin, previously isolated from Narcissus tazetta and Lilium auratum. 4. Isoquercitrin, previously reported to be present in pear leaves, was isolated from the fruit of Bon Chrétien pears. 5. The isolated glycosides were present in the peels and flesh of the fruit, but were absent from the cores. PMID:16749105

  8. Glycosidic aroma precursors of Syrah and Chardonnay grapes after an oak extract application to the grapevines.

    PubMed

    Martínez-Gil, Ana M; Angenieux, Magaly; Pardo-García, Ana I; Alonso, Gonzalo L; Ojeda, Hernán; Rosario Salinas, M

    2013-06-01

    Syrah and Chardonnay grapevines were treated with an oak extract in order to determine the effect on glycosidic aroma precursors. Grapevines were treated at three different timings of the veraison (treatment 1, 2 and 3). Aglycons were obtained by enzymatic hydrolysis, and these were identified and quantified by means of gas chromatography-mass spectrometry (GC-MS). Results suggest that after the applications the majority of compounds from the oak extract were assimilated and stored as glycosidic forms in both cultivars. Also, other compounds not present in the extract were affected, with a different behaviour observed depending on the timing of application and the variety. In general, C6 compounds, alcohols, terpenes, phenols and C13-norisoprenoids in Syrah showed a decrease and in Chardonnay an increase. Thus, this study proved a change in the glycosidic aroma profile in grapes after the oak application, so these treated grapes could produce wines with different aromatic quality. PMID:23411201

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

    PubMed

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

    2014-01-01

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

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

    PubMed Central

    2014-01-01

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

  11. The Genetic Basis for Variation in the Concentration of Phenolic Glycosides in Salix sericea: an Analysis of Heritability

    Microsoft Academic Search

    COLIN M. ORIANS; BERNADETTE M. ROCHEt; ROBERT S. FRlTZt

    1998-01-01

    Willows and many other members of the Salicaceae often produce phenolic glycosides, and the concentrations of these are known to vary among plants. We used progeny from a factorial half-sib quantitative genetics experiment with Salix sericea to determine whether the concentration of two phenolic glycosides, salicortin and 2'-cinnamoylsalicortin, show additive heritability. We found that the con- centration of salicortin was

  12. The genetic basis for variation in the concentration of phenolic glycosides in Salix sericea: an analysis of heritability

    Microsoft Academic Search

    Colin M. Orians; Bernadette M. Roche; Robert S. Fritz

    1996-01-01

    Willows and many other members of the Salicaceae often produce phenolic glycosides, and the concentrations of these are known to vary among plants. We used progeny from a factorial half-sib quantitative genetics experiment with Salix sericea to determine whether the concentration of two phenolic glycosides, salicortin and 2?-cinnamoylsalicortin, show additive heritability. We found that the concentration of salicortin was much

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

    Microsoft Academic Search

    Jean-François Gonnet

    1996-01-01

    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

  14. 1,2-cis Alkyl glycosides: straightforward glycosylation from unprotected 1-thioglycosyl donors.

    PubMed

    Meng, Bo; Zhu, Zhenqian; Baker, David C

    2014-07-28

    A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions. PMID:24915049

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

    PubMed

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

    2011-01-01

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

  16. Two new acylated flavanone glycosides from the leaves and branches of Phyllanthus emblica.

    PubMed

    Zhang, Ying-Jun; Abe, Tomomi; Tanaka, Takashi; Yang, Chong-Ren; Kouno, Isao

    2002-06-01

    Two new acylated flavanone glycosides, (S)-eriodictyol 7-O-(6"-O-trans-p-coumaroyl)-beta-D-glucopyranoside (1) and (S)-eriodictyol 7-O-(6"-O-galloyl)-beta-D-glucopyranoside (2) were isolated from the leaves and branches of Phyllanthus emblica together with a new phenolic glycoside, 2-(2-methylbutyryl)phloroglucinol 1-O-(6"-O-beta-D-apiofuranosyl)-beta-D-glucopyranoside (3), as well as 22 known compounds. Their structures were determined by spectral and chemical methods. PMID:12045344

  17. Note: A new biologically active flavonol glycoside from Psoralea corylifolia (Linn.)

    Microsoft Academic Search

    R. N. Yadava; Vikash Verma

    2005-01-01

    A new biologically active flavonol glycoside (1) mp 264–265°C, C32H38O20, [M] 742 (EIMS) has been isolated from the methanol-soluble fraction of the defatted seeds of Psoralea corylifolia (Linn.). It was characterised as the new flavonol glycoside 3,5,3?,4?-tetrahydroxy-7-methoxyflavone-3?-O-?-l-xylopyranosyl(1?3)-O-?-l-arabinopyranosyl(1?4)-O-?-d-galactopyranoside by several colour reactions, spectral analysis and chemical degradations. Compound 1 showed anti-microbial activity against various bacteria and fungi.

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

    PubMed

    Yadava, R N; Verma, Vikash

    2003-03-01

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

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

    NASA Astrophysics Data System (ADS)

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

    2010-11-01

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

  20. Flavonoid glycosides of spore-bearing stems of Equisetum arvense

    Microsoft Academic Search

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

    1980-01-01

    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

  1. Violarvensin, a new flavone di-C-glycoside from Viola arvensis.

    PubMed

    Carnat, A P; Carnat, A; Fraisse, D; Lamaison, J L; Heitz, A; Wylde, R; Teulade, J C

    1998-02-01

    A new flavonoid di-C-glycoside, violarvensin (1), was isolated from the aerial parts of Viola arvensis, together with the known derivative violanthin (2). The structure of 1 was established as apigenin-6-C-beta-D-glucopyranosyl-8-C-beta-D-6-deoxygulopyrano side by spectral analysis. PMID:9548860

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

    PubMed

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

    2012-08-11

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

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

    PubMed

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

    2015-01-01

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

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

  5. 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...

  6. Degradation of cyanogenic glycosides by Lactobacillus plantarum strains from spontaneous cassava fermentation and other microorganisms

    Microsoft Academic Search

    Vicki Lei; Wisdom Kofi Asa Amoa-Awua; Leon Brimer

    1999-01-01

    Strains of Lactobacillus plantarum, Leuconostoc mesenteroides, Candida tropicalis and Penicillium sclerotiorum were screened for 19 enzymatic activities using the commercial kit API zym (Bio Mérieux). This activity was compared to the ability of degrading the toxic cyanogenic glycosides amygdalin, linamarin, and linseed cyanogens (a mixture of linustatin and neolinustatin). Good correlation between the ?-glucosidase activity found in the API zym

  7. 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...

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

    Microsoft Academic Search

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

    2004-01-01

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

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

    PubMed

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

    2014-11-21

    During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycoside phyllaemblicins G1–G8 (1–8) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin F (9), phyllaemblic acid (10) and glochicoccin D (11). Phyllaemblicin G2 (2), bearing a tricyclo [3.1.1.1] oxygen bridge ring system, is an unusual sesquiterpenoid glycoside, while phyllaemblicins G6–G8 (6–8) are dimeric sesquiterpenoid glycosides with two norbisabolane units connecting through a disaccharide. All the structures were elucidated by the extensive analysis of HRMS and NMR data. The relative configuration of phyllaemblicin G2 was constructed based on heteronuclear coupling constants measurement, and the absolute configurations for all new compounds were established by calculated electronic circular dichroism (ECD) using time dependent density functional theory. The sesquiterpenoid glycoside dimers 6–9 displayed potential anti-hepatitis B virus (HBV) activities, especially for the new compound 6 with IC50 of 8.53 ± 0.97 and 5.68 ± 1.75 ?M towards the HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively. PMID:25268491

  10. A new 2'-oxygenated flavone glycoside from Litsea glutinosa (Lour.) C. B. Rob.

    PubMed

    Wang, Yun-Song; Huang, Rong; Lu, Hao; Li, Feng-Ya; Yang, Jing-Hua

    2010-01-01

    A new 2'-oxygenated flavone glycoside, named glutin, was isolated from Litsea glutinosa (Lour.) C. B. Rob. along with four known compounds. The structure was identified as 2',5,7-trihydroxy-6-methoxyflavone 2'-O-beta-D-glucopyranoside (1) on the basis of extensive spectroscopic analysis. PMID:20208374

  11. The induction of intestinal neoplasms in rats with the glycoside cycasin and its aglycone

    Microsoft Academic Search

    Gert L. Laqueur

    1965-01-01

    Experiments are described dealing with the carcinogenic effects of (1) the crude cycad seed material, (2) the glycoside, cycasin, aß-D-glucosyloxyazoxymethane, isolated from the crude material, and (3) the first metabolic breakdown product of cycasin, the aglycone of cycasin or methylazoxymethanol, on the intestinal tract of rats. While the crude material and cycasin produced tumors exclusively located in the large intestine,

  12. Estrogenic activity of triterpene glycosides in yeast two-hybrid assay.

    PubMed

    Kovalchuk, S N; Kozhemyako, V B; Atopkina, L N; Silchenko, A S; Avilov, S A; Kalinin, V I; Rasskazov, V A; Aminin, D L

    2006-11-01

    Estrogenic potency of six triterpene glycosides, Holothurin A, Holotoxin A1, Frondoside A, Cucumarioside A2-2 and Cauloside C, that are natural products and semi-synthesized Ginsenoside-Rh2, were examined with yeast two-hybrid system, including expressed genes of human estrogen receptor, hERalpha, the co-activator TIF2 and lacZ as a reporter gene. Only Ginsenoside-Rh2 exhibited significant moderate estrogenic activity in the concentration range of 10(-7) to 10(-6)M. Its effect was approximately 30% of the activity of 17beta-estradiol applied at half-effective concentration. This indicates Ginsenosides-Rh2 is a weak phytoestrogen. The sea cucumber triterpene glycosides, Holothurin A, Holotoxin A1, Cucumarioside A2-2 and Frondoside A, and plant glycoside Cauloside C had no appreciable estrogenic activity. Data obtained by yeast two-hybrid assay reflect structure-activity relationship between tested compounds and 17beta-estradiol. Only Ginsenoside-Rh2 has some similarity in chemical structure with 17beta-estradiol that might explain affinity of this glycoside to the hERalpha receptor. PMID:16973351

  13. New cardiac glycosides containing 2-deoxyhexoses from the defensive secretion of adult Chrysolina banksi (Coleoptera: Chrysomelidae)

    Microsoft Academic Search

    Désiré Daloze; Fabienne Broeders; Jean-Claude Braekman; Jorge Araujo; Jacques M. Pasteels

    1995-01-01

    Four new cardenolides, 2–5, have been isolated together with adenosine from the defensive secretion of adult Chrysolina banksi beetles and their structures determined by spectroscopic methods. All these glycosides contain periplogenin as aglycone and are characterized by the unprecedented occurrence of 2-deoxy-ß-lyxo-hexopyranose and 2-deoxy-ß-xylo-hexopyranose. The taxonomic implications of these results are discussed.

  14. In vitro degradation of the flavonol quercetin and of quercetin glycosides in the porcine hindgut

    Microsoft Academic Search

    Rainer Cermak; Gerhard Breves; Matthias Lüpke; Siegfried Wolffram

    2006-01-01

    The present study investigated the microbial degradation of the plant flavonol quercetin and its naturally occurring glycosides isoquercitrin and rutin in the porcine hindgut. The experiments were carried out with the semicontinuous colon-simulation technique. The fluid and particle phase of pig hindgut contents from freshly slaughtered animals were used for the in vitro incubations. Following a five-day equilibration period, quercetin,

  15. Acylated 5,7,2',6'-oxygenated flavone glycosides from Andrographis alata.

    PubMed

    Das, Biswanath; Ramu, R; Rao, Yerra Koteswara; Reddy, M Ravinder; Harish, H; Reddy, V Saidi; Ramakrishna, K V S

    2006-05-01

    Five acylated 5,7,2',6'-oxygenated flavone glycosides along with the known 5,2',6'-trihydroxy-7-methoxyflavone-2'-O-beta-d-glucopyranoside have been isolated from the whole plant of Andrographis alata. The structures of the compounds were established from spectral (mainly 1D and 2D NMR) and chemical studies. PMID:16624351

  16. Acylated 5,7,2?,6?-oxygenated flavone glycosides from Andrographis alata

    Microsoft Academic Search

    Biswanath Das; R. Ramu; Yerra Koteswara Rao; M. Ravinder Reddy; H. Harish; V. Saidi Reddy; K. V. S. Ramakrishna

    2006-01-01

    Five acylated 5,7,2?,6?-oxygenated flavone glycosides along with the known 5,2?,6?-trihydroxy-7-methoxyflavone-2?-O-?-d-glucopyranoside have been isolated from the whole plant of Andrographis alata. The structures of the compounds were established from spectral (mainly 1D and 2D NMR) and chemical studies.

  17. Phenolic glycosides govern the food selection pattern of willow feeding leaf beetles

    Microsoft Academic Search

    J. Tahvanainen; R. Julkunen-Tiitto; J. Kettunen

    1985-01-01

    The relationship between the food selection of four leaf beetle species (Phratora vitellinae, Plagiodera versicolora, Lochmaea capreae, Galerucella lineola) and the phenolic glycosides of willow (Salix spp.) leaves was tested in laboratory food choice experiments. Four willow species native to the study area (Eastern Finland) and four introduced, cultivated willows were tested.

  18. ?-Glucosidase inhibitory activities of phenylpropanoid glycosides, vanicoside A and B from Polygonum sachalinense rhizome

    Microsoft Academic Search

    Y. Kawai; H. Kumagai; H. Kurihara; K. Yamazaki; R. Sawano; N. Inoue

    2006-01-01

    The phenylpropanoid glycosides, vanicoside A and B, isolated from rhizomes of giant knotweed (Polygonum sachalinense) showed ?-glucosidase inhibitory activity, with IC50 values of 59.8 and 48.3 ?g\\/ml (59.9 and 50.5 ?M), respectively. In contrast, p-coumaric acid and ferulic acid, corresponding to phenylpropanoyl moieties of vanicosides, exhibited very little inhibition.

  19. Hydrolysis of terpenyl glycosides in grape juice and other fruit juices: a review

    Microsoft Academic Search

    Sergi Maicas; José Juan Mateo

    2005-01-01

    The importance of monoterpenes on varietal flavour of must and other fruit juices has been reviewed. These compounds were mainly found linked to sugar moieties in grape juice and wines, showing no olfactory characteristics. In this way, analytical techniques developed to study these compounds, in both free or glycosidically forms, are discussed. Mechanisms to liberate terpenes were studied, making a

  20. [Development of Tripterygium glycosides nano-carries based on "nanoemulsion-gels" and its pharmacodynamics].

    PubMed

    Gu, Qing; You, Ben-Ming; Yang, Di-Shun; Pan, Yong-Hua; Shu, Wei; Liu, Ji-Yong

    2015-01-01

    The aim of this study is to develop the Tripterygium glycosides nanoemulsion gels and investigate its pharmacodynamics. Oleic acid was used as oil phase, polyoxyethylene castor oil as surfaetant, and 1,2-propanediol as cosurfactant to screen the formula of Tripterygium glycoside nanoemulsion using the pseudo-temary phase diagrams. Then the nanoemulsion gels was prepared. The ICR mouse ears were sensitazated by 7% DNCB, and then were excited by 0.3% DNCB to stimulate the model of mouse chronic dermatitis and eczema. The concentrations of IFN-?, IL-4 and IL-8 in mouse blood were determined by ELISA. The results showed that Tripterygium glycosides nanoemulsion gels could significantly inhibit the swelling of mouse ears(P < 0.01) and ameliorate the edama and erythema of model mouse ears skin. Also it could significantly decrease the expression of IFN-? and IL-4 in model mouse blood. Tripterygium glycosides nanoemulsion gels had a good therapeutic effect on mouse model of dermatitis and eczema. It was expected to provide a new and long-acting exterernal preparation for the treatment of dermatitis and eczema. PMID:25993791

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

    PubMed Central

    2012-01-01

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

  2. The flavonoid glycosides and procyanidin composition of Deglet Noor dates (Phoenix dactylifera).

    PubMed

    Hong, Yun Jeong; Tomas-Barberan, F A; Kader, Adel A; Mitchell, Alyson E

    2006-03-22

    The fruits of the date palm (Phoenix dactylifera) are consumed throughout the world and are an important part of the diet in the Middle East. Dates at the rutab and tamar maturity and ripening stages contain a wide array of phenolic antioxidants, but little is known about the composition of phenolic compounds in dates at the khalal stage of ripening. In the current study, the flavonoid glycoside and procyanidin compositions of dates of the cultivar Deglet Noor harvested at the khalal stage of maturity were characterized using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI/MS/MS). Procyanidin oligomers through decamers were identified in extracts of these dates. Higher molecular weight polymers, undecamers through heptadecamers, were also apparent from mass spectra. Thirteen flavonoid glycosides of luteolin, quercetin, and apigenin, 19 when considering isomeric forms, were also identified. Mass spectra indicate that both methylated and sulfated forms of luteolin and quercetin are present as mono-, di-, and triglycosylated conjugates whereas apigenin is present as only the diglycoside. LC-ESI/MS/MS spectra indicate that quercetin and luteolin formed primarily O-glycosidic linkages whereas apigenin is present as the C-glycoside. PMID:16536626

  3. Synthesis of the C-glycoside of ?-D-mannose-(1 ? 6)-d-myo-inositol†

    PubMed Central

    Hans, Sunej; Altiti, Ahmad; Mootoo, David R.

    2015-01-01

    The dimannosylatedinositol pseudotrisaccharide phospholipid of the lipoarabinomannan (LAM) component of the mycobacterial cell wall has attracted interest as a therapeutic target because of its uniqueness to mycobacteria, its assembly at an early stage in LAM biosynthesis and the immunological activity of oligosaccharides containing this subunit. Accordingly, analogues of this pseudotrisaccharide, ?-d-mannose-(1 ? 2)-?-d-mannose-(1 ? 6)-d-myo-inositol are of interest as mechanistic probes and drug leads. C-glycosides are of special interest because of their hydrolytic stability and conformational differences compared to O-glycosides. Herein, as a prelude to C-glycoside analogues of this pseudotrisaccharide, we describe the synthesis of the C-glycoside of ?-D-mannose-(1 ? 6)-d-myo-inositol. The synthetic strategy centers on the elaboration of a C1-linked glycal-inositol, the glycone segment of which is assembled via an oxocarbenium ion cyclization on a thioacetal-enol ether precursor that originates from “glycone” and “aglycone” components. PMID:24057020

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

    Microsoft Academic Search

    Sudesh Kumar Yadav; Praveen Guleria

    2012-01-01

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

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

    Microsoft Academic Search

    Sudesh Yadav; Praveen Guleria

    2011-01-01

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

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

    PubMed

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

    2010-12-01

    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

  7. Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: their inhibitory activities for rat lens aldose reductase.

    PubMed

    Matsuda, Hisashi; Morikawa, Toshio; Toguchida, Iwao; Harima, Shoichi; Yoshikawa, Masayuki

    2002-07-01

    Two new flavanone glycosides, (2S)- and (2R)-eriodictyol 7-O-beta-D-glucopyranosiduronic acids, and a new phenylbutanoid glycoside, (2S, 3S)-1-phenyl-2,3-butanediol 3-O-beta-D-glucopyranoside, were isolated from the flowers of Chrysanthemum indicum L. cultivated in China together with eight flavonoids. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. Both of the new flavanone glycosides were found to show inhibitory activity for rat lens aldose reductase. PMID:12130858

  8. Supplementing with Non-Glycoside Hydrolase Proteins Enhances Enzymatic Deconstruction of Plant Biomass

    PubMed Central

    Su, Xiaoyun; Zhang, Jing; Mackie, Roderick I.; Cann, Isaac K. O.

    2012-01-01

    The glycoside hydrolases (GH) of Caldicellulosiruptor bescii are thermophilic enzymes, and therefore they can hydrolyze plant cell wall polysaccharides at high temperatures. Analyses of two C. bescii glycoside hydrolases, CbCelA-TM1 and CbXyn10A with cellulase and endoxylanase activity, respectively, demonstrated that each enzyme is highly thermostable under static incubation at 70°C. Both enzymes, however, rapidly lost their enzymatic activities when incubated at 70°C with end-over-end shaking. Since crowding conditions, even at low protein concentrations, seem to influence enzymatic properties, three non-glycoside hydrolase proteins were tested for their capacity to stabilize the thermophilic proteins at high temperatures. The three proteins investigated were a small heat shock protein CbHsp18 from C. bescii, a histone MkHistone1 from Methanopyrus kandleri, and bovine RNase A, from a commercial source. Fascinatingly, each of these proteins increased the thermostability of the glycoside hydrolases at 70°C during end-over-end shaking incubation, and this property translated into increases in hydrolysis of several substrates including the bioenergy feedstock Miscanthus. Furthermore, MkHistone1 and RNase A also altered the initial products released from the cello-oligosaccharide cellopentaose during hydrolysis with the cellodextrinase CbCdx1A, which further demonstrated the capacity of the three non-GH proteins to influence hydrolysis of substrates by the thermophilic glycoside hydrolases. The non-GH proteins used in the present report were small proteins derived from each of the three lineages of life, and therefore expand the space from which different polypeptides can be tested for their influence on plant cell wall hydrolysis, a critical step in the emerging biofuel industry. PMID:22952777

  9. Flavan-3-ol C-glycosides--preparation and model experiments mimicking their human intestinal transit.

    PubMed

    Hasslauer, Iris; Oehme, Anett; Locher, Sanja; Valotis, Anagnostis; Van't Slot, Gordon; Humpf, Hans-Ulrich; Schreier, Peter

    2010-11-01

    In order to study the human intestinal transit of flavan-3-ol C-glycosides, several C-glycosyl derivatives were prepared by non-enzymatic reaction of (+)-catechin with ?-D-glucose, ?-D-galactose and ?-D-rhamnose, respectively. In contrast to literature data, we propose that the reaction mechanism proceeds in analogy to the rearrangement of flavan-3-ols during epimerization under alkaline conditions. Four of the 12 synthesized flavan-3-ol C-glycosides were incubated under aerobic conditions at 37°C using saliva (2 min) and simulated gastric juice (3 h). To simulate human intestine, the C-glycosides were also incubated under anaerobic conditions at 37°C both in human ileostomy fluid (10 h) and colostomy fluid (24 h), respectively. The flavan-3-ol C-glycosides under study, i.e. (+)-epicatechin 8-C-?-D-glucopyranoside (1a), (+)-epicatechin 6-C-?-D-glucopyranoside (1d), (+)-catechin 6-C-?-D-galactopyranoside (2b), (+)-catechin 6-C-?-D-rhamnopyranoside (3b) were analyzed in the incubation samples by HPLC-DAD and HPLC-DAD-MS/MS. They were found to be stable in the course of incubation in saliva, simulated gastric juice and ileostomy fluid and underwent degradation in colostomy fluid. While the 6-C-?-D-glucopyranoside 1d was completely metabolized between 2 and 4 h, decomposition of the 6-C-?-D-galactopyranoside 2b reached only 16 ± 2% within 4 h of incubation. Linear degradation rates of 1d and 2b in colostomy fluid differed significantly. As microbial metabolism of flavan-3-ols is known not to be influenced by the stereochemistry of the aglycon, varying degradation rates are ascribed to the effect of the sugar moiety. Based on these results we assume that flavan-3-ol C-glycosides pass through the upper gastrointestinal tract (oral cavity, stomach and small intestine) unmodified and are then metabolized by the colonic microflora. PMID:20468005

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

    PubMed

    Su, Xiaoyun; Zhang, Jing; Mackie, Roderick I; Cann, Isaac K O

    2012-01-01

    The glycoside hydrolases (GH) of Caldicellulosiruptor bescii are thermophilic enzymes, and therefore they can hydrolyze plant cell wall polysaccharides at high temperatures. Analyses of two C. bescii glycoside hydrolases, CbCelA-TM1 and CbXyn10A with cellulase and endoxylanase activity, respectively, demonstrated that each enzyme is highly thermostable under static incubation at 70°C. Both enzymes, however, rapidly lost their enzymatic activities when incubated at 70°C with end-over-end shaking. Since crowding conditions, even at low protein concentrations, seem to influence enzymatic properties, three non-glycoside hydrolase proteins were tested for their capacity to stabilize the thermophilic proteins at high temperatures. The three proteins investigated were a small heat shock protein CbHsp18 from C. bescii, a histone MkHistone1 from Methanopyrus kandleri, and bovine RNase A, from a commercial source. Fascinatingly, each of these proteins increased the thermostability of the glycoside hydrolases at 70°C during end-over-end shaking incubation, and this property translated into increases in hydrolysis of several substrates including the bioenergy feedstock Miscanthus. Furthermore, MkHistone1 and RNase A also altered the initial products released from the cello-oligosaccharide cellopentaose during hydrolysis with the cellodextrinase CbCdx1A, which further demonstrated the capacity of the three non-GH proteins to influence hydrolysis of substrates by the thermophilic glycoside hydrolases. The non-GH proteins used in the present report were small proteins derived from each of the three lineages of life, and therefore expand the space from which different polypeptides can be tested for their influence on plant cell wall hydrolysis, a critical step in the emerging biofuel industry. PMID:22952777

  11. Time-reversal mirrors

    Microsoft Academic Search

    M. Fink

    1993-01-01

    Time-reversal of ultrasonic fields allows a very efficient approach to focus pulsed ultrasonic waves through inhomogeneous media. Time-reversal mirrors (TRMS) are made of large transducer arrays, allowing the incident acoustic field to be sampled, time-reversed and re-emitted. The paper introduces the time-reversal approach in a discussion of the techniques used in optics for focusing through inhomogeneous media. The discussion is

  12. Reverse Correlation in Neurophysiology

    ERIC Educational Resources Information Center

    Ringach, Dario; Shapley, Robert

    2004-01-01

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

  13. Time-reversed acoustics

    Microsoft Academic Search

    Mathias Fink; Didier Cassereau; Arnaud Derode; Claire Prada; Philippe Roux; Mickael Tanter; Jean-Louis Thomas; François Wu

    2000-01-01

    The objective of this paper is to show that time reversal invariance can be exploited in acoustics to create a variety of useful instruments as well as elegant experiments in pure physics. Section 1 is devoted to the description of time reversal cavities and mirrors together with a comparison between time reversal and phase conjugation. To illustrate these concepts, several

  14. Ultrasonic Time Reversal Mirrors

    Microsoft Academic Search

    Mathias Fink; Gabriel Montaldo; Mickael Tanter

    2004-01-01

    For more than ten years, time reversal techniques have been developed in many different fields of applications including detection of defects in solids, underwater acoustics, room acoustics and also ultrasound medical imaging and therapy. The essential property that makes time reversed acoustics possible is that the underlying physical process of wave propagation would be unchanged if time were reversed. In

  15. Identification and quantitation of glycosidically bound aroma compounds in three tobacco types by gas chromatography-mass spectrometry.

    PubMed

    Cai, Kai; Xiang, Zhangmin; Pan, Wenjie; Zhao, Huina; Ren, Zhu; Lei, Bo; Geng, Zhaoliang

    2013-10-11

    Glycosidically bound aroma compounds in three different types of tobacco were investigated. After isolation of extracts obtained by Amberlite XAD-2 adsorption and ethyl acetate elution, glycosides were analyzed after enzymatic hydrolysis by gas chromatography-mass spectrometry (GC-MS) or directly after trifluoroacetylated (TFA) derivatization by GC-MS in electron ionization (EI) and negative chemical ionization (NCI) mode. In total 21 bound aglycones were identified by ?-glucosidase hydrolysis. These aglycones mainly consisted of C13-norisoprenoids, aromatic components and sesquiterpenoids. Additionally, with the aid of enzymatic hydrolysis, 15 ?-d-glucopyranosides and 1 ?-d-rutinoside were tentatively identified by TFA derivatization. TFA method was validated by repeatability and successfully employed to analyze different types of tobacco. Principal component analysis (PCA) was carried out on identified glycoside variables to visualize the difference between the tobacco types and the relationship between the glycoside variables and the tobacco types was established. PMID:24011421

  16. Extraction and purification of flavanone glycosides and kaemferol glycosides from defatted Camellia oleifera seeds by salting-out using hydrophilic isopropanol

    Microsoft Academic Search

    Jung-Hui Chen; Bing-Chung Liau; Ting-Ting Jong; Chieh-Ming J. Chang

    2009-01-01

    The purpose of this research was to investigate a salting-out procedure for isolating four flavonoid glycosides from defatted Camellia oleifera seeds. The procedure included extraction with 80% methanol, methanol removal and addition of an equal amount of hydrophilic isopropanol and salt to separate the isopropanol fraction from the water layer. Using successive column chromatography, kaemferol-3-O-[2-O-?-d-glucopyranosyl-6-O-?-l-rhamnopyranosyl]-?-d-glucopyranoside (compound 1), kaemferol-3-O-[2-O-?-d-xylopyranosyl-6-O-?-l-rhamnopyranosyl]-?-d-glucopyranoside (compound 2),

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

    Microsoft Academic Search

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

    2003-01-01

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

  18. Column liquid chromatographic determination of flavanone glycosides in Citrus. Application to grapefruit and sour orange juice adulterations.

    PubMed

    Mouly, P; Gaydou, E M; Estienne, J

    1993-03-12

    Six flavone glycosides were separated by HPLC using RP-18 with a quaternary mobile phase mixture [water-acetonitrile-tetrahydrofuran-acetic acid (80:16:3:1, v/v)]. This procedure was applied to the separation and determination of the most important flavanone glycosides contained in pure grapefruit and sour orange juices and mixtures. This method can be used for quality control of industrial concentrates and juices. PMID:8486744

  19. Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells

    Microsoft Academic Search

    Hak Ju Lee; Ha Young Kang; Cheol Hee Kim; Hyo Sung Kim; Min Chul Kwon; Sang Moo Kim; Il Shik Shin; Hyeon Yong Lee

    2006-01-01

    A new compound, rotenoid isoflavone glycoside named, 6?-O-?-d-glucopyranosyl-12a-hydroxydalpanol was isolated from the methanolic (MeOH) fruit extract of Amorpha fruticosa LINNE by means of multi-stage column chromatography. Immuno-modulatory activities of this new glycoside were compared with\\u000a the partitioned fractions of Amorpha fruticosa LINNE. Both of the fractions and purified single compound showed a 19% relatively low cytotoxicity at a maximum concentration

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

    Microsoft Academic Search

    Colin M. Orians; Robert S. Fritz

    1995-01-01

    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

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

    PubMed Central

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

    2013-01-01

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

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

    PubMed

    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

    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. PMID:25800015

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

    PubMed

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

    2015-07-01

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

  4. Novel acetylated chalcone and biflavonoid glycosides from Trigonosciadium brachytaenium (Boiss.) Alava.

    PubMed

    Akhavan, Malihe; Shafaghat, Ali; Salimi, Farshid

    2013-01-01

    A new acetylated chalcone glycoside, trans-2',6'-dihydroxy-4'-O-(4?-acetyl-rhamnoside)-4-methoxychalcone (1) and a new biflavonoid glycosides, 5,3',5?,4?'-tetrahydroxy-3?',5?'dimethoxy-biflavone (4' ? 8?)-7-O-((2-rhamnoside) rhamnoside) (2) were isolated from the ethyl acetate soluble fraction of the methanol extract obtained from Trigonosciadium brachytaenium and have been purified by column chromatography and preparative TLC. Those structures were elucidated by UV, (1)H NMR and (13)C NMR, HMBC, EI-MS and IR spectra. The antioxidant activity of ethyl acetate extract was evaluated by 1,1-diphenyl-2-picrylhydrazyl method. The results indicate that ethyl acetate extract from aerial part of T. brachytaenium possesses considerable antioxidant activity. PMID:23631351

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

    PubMed Central

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

    2014-01-01

    Many marine triterpene glycosides have in vitro and in vivo activities with very low toxicity, suggesting that they are suitable agents for the prevention and treatment of different diseases, particularly cancer. However, the molecular mechanisms of action of natural marine compounds in cancer, immune, and other various cells are not fully known. This review focuses on the structural characteristics of marine triterpene glycosides and how these affect their biological activities and molecular mechanisms. In particular, the membranotropic and membranolytic activities of frondoside A and cucumariosides from sea cucumbers and their ability to induce cytotoxicity and apoptosis have been discussed, with a focus on structure-activity relationships. In addition, the structural characteristics and antitumor effects of stichoposide C and stichoposide D have been reviewed along with underlying their molecular mechanisms. PMID:25250309

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

    PubMed

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

    2005-01-01

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

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

    PubMed

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

    2008-01-01

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

  8. Two New Triterpene Glycosides from the Vietnamese Sea Cucumber Holothuria scabra

    Microsoft Academic Search

    Nguyen Hai Dang; Nguyen Van Thanh; Phan Van Kiem; Le Mai Huong; Chau Van Minh; Young Ho Kim

    2007-01-01

    Two new triterpene glycosides, namely holothurin A3 (1) and A4 (2) were isolated from the methanol extract of the sea cucumber,Holothuria scabra, with their structures elucidated from the spectroscopic evidence (1D NMR, 2D NMR, ESI-MS and HRESI-MS). Compounds1 and2 were found to be strongly cytotoxic to both cancer cell lines, KB and Hep-G2, with 50% inhibitory concentrations (IC50) of 0.87

  9. The iridoid glycoside, catalpol, as a deterrent to the predator Camponotus floridanus (Formicidae)

    Microsoft Academic Search

    Marie-Ann de la Fuente; Lee A. Dyer; M. Deane Bowers

    1994-01-01

    Summary We investigated the role of the iridoid glycoside, catalpol, as a deterrent to the predator,Camponotus floridanus. Four laboratory colonies of this ant were offered buckeye caterpillars (Junonia coenia: Nymphalidae) raised on diets with and without catalpol. The same colonies were offered sugar-water solutions containing varying concentrations of catalpol, in both no-choice and choice tests. Regardless of diet, buckeye caterpillars

  10. Icaritin and its glycosides enhance osteoblastic, but suppress osteoclastic, differentiation and activity in vitro

    Microsoft Academic Search

    Jian Huang; Lan Yuan; Xi Wang; Tian-Lan Zhang; Kui Wang

    2007-01-01

    Icariin, a principal flavonoid glycoside in Herba Epimedii, is hypothesized to possess beneficial effects on bone mass. Icariin is metabolized to icariside II and then to icaritin in vivo. In the present study, we investigated the in vitro effects of icariin, icariside II and icaritin on both osteoblasts and osteoclasts. After treatment with these compounds at concentrations 10?5–10?8 mol\\/l, osteoblasts were

  11. Specificity of Phenolic Glycoside Induction in Willow Seedlings ( Salix sericea ) in Response to Herbivory

    Microsoft Academic Search

    Mark J. Fields; Colin M. Orians

    2006-01-01

    Salix sericea (Marsh.) (Salicaceae) seedlings were used to investigate phytochemical induction of phenolic glycosides following beetle herbivory. Seven-week-old full-sibling seedlings were subjected to one of three damage treatments: Plagiodera versicolora adults, P. versicolora larvae, or Calligrapha multipunctata bigsbyana adults. Salicylate concentrations were measured locally (within damaged leaves) and systemically (above and below damaged leaves) 4 d later. Herbivory caused differential salicylate

  12. Biosynthesis of Phenolic Glycosides from Phenylpropanoid and Benzenoid Precursors in Populus

    Microsoft Academic Search

    Benjamin A. Babst; Scott A. Harding; Chung-Jui Tsai

    2010-01-01

    Salicylate-containing phenolic glycosides (PGs) are abundant and often play a dominant role in plant-herbivore interactions\\u000a of Populus and Salix species (family Salicaceae), but the biosynthetic pathway to PGs remains unclear. Cinnamic acid (CA) is thought to be a precursor\\u000a of the salicyl moiety of PGs. However, the origin of the 6-hydroxy-2-cyclohexen-on-oyl (HCH) moiety found in certain PGs,\\u000a such as salicortin,

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

    Microsoft Academic Search

    Jose M. Prieto; Tiziana Siciliano; Alessandra Braca

    2006-01-01

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

  14. Estrogenic activity of triterpene glycosides in yeast two-hybrid assay

    Microsoft Academic Search

    S. N. Kovalchuk; V. B. Kozhemyako; L. N. Atopkina; A. S. Silchenko; S. A. Avilov; V. I. Kalinin; V. A. Rasskazov; D. L. Aminin

    2006-01-01

    Estrogenic potency of six triterpene glycosides, Holothurin A, Holotoxin A1, Frondoside A, Cucumarioside A2-2 and Cauloside C, that are natural products and semi-synthesized Ginsenoside-Rh2, were examined with yeast two-hybrid system, including expressed genes of human estrogen receptor, hER?, the co-activator TIF2 and lacZ as a reporter gene. Only Ginsenoside-Rh2 exhibited significant moderate estrogenic activity in the concentration range of 10?7

  15. Mesophyll distribution of ‘antioxidant’ flavonoid glycosides in Ligustrum vulgare leaves under contrasting sunlight irradiance

    PubMed Central

    Agati, Giovanni; Stefano, Giovanni; Biricolti, Stefano; Tattini, Massimiliano

    2009-01-01

    Background and Aims Flavonoids have the potential to serve as antioxidants in addition to their function of UV screening in photoprotective mechanisms. However, flavonoids have long been reported to accumulate mostly in epidermal cells and surface organs in response to high sunlight. Therefore, how leaf flavonoids actually carry out their antioxidant functions is still a matter of debate. Here, the distribution of flavonoids with effective antioxidant properties, i.e. the orthodihydroxy B-ring-substituted quercetin and luteolin glycosides, was investigated in the mesophyll of Ligustrum vulgare leaves acclimated to contrasting sunlight irradiance. Methods In the first experiment, plants were grown at 20 % (shade) or 100% (sun) natural sunlight. Plants were exposed to 100 % sunlight irradiance in the presence or absence of UV wavelengths, in a second experiment. Fluorescence microspectroscopy and multispectral fluorescence microimaging were used in both cross sections and intact leaf pieces to visualize orthodihydroxy B-ring-substituted flavonoids at inter- and intracellular levels. Identification and quantification of individual hydroxycinnamates and flavonoid glycosides were performed via HPLC-DAD. Key Results Quercetin and luteolin derivatives accumulated to a great extent in both the epidermal and mesophyll cells in response to high sunlight. Tissue fluorescence signatures and leaf flavonoid concentrations were strongly related. Monohydroxyflavone glycosides, namely luteolin 4?-O-glucoside and two apigenin 7-O-glycosides were unresponsive to changes in sunlight irradiance. Quercetin and luteolin derivatives accumulated in the vacuoles of mesophyll cells in leaves growing under 100 % natural sunlight in the absence of UV wavelengths. Conclusions The above findings lead to the hypothesis that flavonoids play a key role in countering light-induced oxidative stress, and not only in avoiding the penetration of short solar wavelengths in the leaf. PMID:19633310

  16. Acid epimerization of 20-keto pregnane glycosides is determined by 2D-NMR spectroscopy

    Microsoft Academic Search

    Víctor P. García

    2011-01-01

    Carbohydrates influence many essential biological events such as apoptosis, differentiation, tumor metastasis, cancer, neurobiology,\\u000a immunology, development, host-pathogen interactions, diabetes, signal transduction, protein folding, and many other contexts.\\u000a We now report on the structure determination of pregnane glycosides isolated from the aerial parts of Ceropegia fusca Bolle (Asclepiadaceae). The observation of cicatrizant, vulnerary and cytostatic activities in some humans and animals

  17. Production of Hesperetin Glycosides by Xanthomonas campestris and Cyclodextrin Glucanotransferase and Their Anti-allergic Activities

    PubMed Central

    Shimoda, Kei; Hamada, Hiroki

    2010-01-01

    The production of hesperetin glycosides was investigated using glycosylation with Xanthomonas campestris and cyclodextrin glucanotransferase (CGTase). X. campestris glucosylated hesperetin to its 3'-, 5-, and 7-O-glucosides, and CGTase converted hesperetin glucosides into the corresponding maltosides. The resulting 7-O-glucoside and 7-O-maltoside of hesperetin showed inhibitory effects on IgE antibody production and on O2- generation from rat neutrophils. PMID:22254014

  18. beta-Glucosidase inhibitory activities of phenylpropanoid glycosides, vanicoside A and B from Polygonum sachalinense rhizome.

    PubMed

    Kawai, Y; Kumagai, H; Kurihara, H; Yamazaki, K; Sawano, R; Inoue, N

    2006-09-01

    The phenylpropanoid glycosides, vanicoside A and B, isolated from rhizomes of giant knotweed (Polygonum sachalinense) showed beta-glucosidase inhibitory activity, with IC(50) values of 59.8 and 48.3 mug/ml (59.9 and 50.5 muM), respectively. In contrast, p-coumaric acid and ferulic acid, corresponding to phenylpropanoyl moieties of vanicosides, exhibited very little inhibition. PMID:16828242

  19. Triterpene glycosides and glucosyl esters, and a triterpene from the leaves of Schefflera actinophylla.

    PubMed

    Wanas, Amira Samir; Matsunami, Katsuyoshi; Otsuka, Hideaki; Desoukey, Samar Yahie; Fouad, Mostafa Ahmed; Kamel, Mohamed Salah

    2010-12-01

    From the EtOAc and 1-BuOH fractions, three new ursane-type and four new lupane-type triterpenes, along with nine known glycosides and glycosyl esters of lupane-type were isolated from the leaves of Schefflera actinophylla. All the isolated compounds were obtained for the first time from this plant. The structures of the new triterpenes were determined through a combination of spectroscopic and chemical analyses. PMID:21139261

  20. Variation in iridoid glycosides in a population of Plantago patagonica Jacq. (Plantaginaceae) in Colorado

    Microsoft Academic Search

    M. Deane Bowers

    1996-01-01

    Plantago patagonica from plants grown in a greenhouse and from a field population in Boulder, Colorado, were sampled for iridoid glycosides. Both aucubin and catalpol were found in P. patagonica, however, not all individual plants contained detectable amounts of both these compounds. Plants grown in the greenhouse (n=8) contained means of 0.26% (±0.04 S.E.) aucubin and 0.23% (±0.05 S.E.) catalpol,

  1. Absolute bioavailability of a Hoodia gordonii steroid glycoside from different physicochemical formats in the pig

    Microsoft Academic Search

    Brigitte A. Graf; Chris J. van Platerink; Gabriella A. M. Ten Have; Nicolaas E. P. Deutz; Krassimir P. Velikov; Leonard M. Flendrig; Sergey M. Melnikov; Ursula M. Garczarek; Salomon L. Abrahamse

    2011-01-01

    Oral administration of extracts of the Hoodia gordonii (H.g.) plant reduced both food intake and body weight in healthy animals. Due to unfavorable physicochemical properties for gastrointestinal dissolution poor oral bioavailability was predicted for the steroid glycoside H.g.-12, a putative active compound in H. gordonii extract. Thus, absolute bioavailability of H.g.-12 was determined in pigs as a function of various

  2. Sedative and anticonvulsant activities of goodyerin, a flavonol glycoside from Goodyera schlechtendaliana.

    PubMed

    Du, Xiao-Ming; Sun, Ning-Yi; Takizawa, Nanako; Guo, Yong-Tian; Shoyama, Yukihiro

    2002-05-01

    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

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

    PubMed Central

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

    2011-01-01

    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

  4. A critical review of the genetic toxicity of steviol and steviol glycosides

    Microsoft Academic Search

    D. J. Brusick

    2008-01-01

    Extracts of the leaves of the stevia plant (Stevia rebaudiana Bertoni) are used to sweeten food and beverages in South America, Japan and China. The components responsible for the sweet properties of the plant are glycosides of steviol, primary stevioside (ent-13-hydroxykaur-16-en-18-oic acid), which is 250–300 times sweeter than sucrose and rebaudiosides A and C. Stevioside and steviol have been subjected

  5. Steviol Glycoside Content in Different Organs of Stevia rebaudiana and Its Dynamics during Ontogeny

    Microsoft Academic Search

    N. I. Bondarev; M. A. Sukhanova; O. V. Reshetnyak; A. M. Nosov

    2003-01-01

    The contents of three major steviol glycosides (SGs) (stevioside and rebaudiosides A and C) in vegetative and generative organs\\u000a during ontogeny of Stevia rebaudiana Bertoni were analysed with HPLC. Plant organs contained different amounts of the SGs, which declined in the following order:\\u000a leaves, flowers, stems, seeds, roots. The highest content of the SGs was found in upper young actively

  6. A comprehensive analysis of fifteen genes of steviol glycosides biosynthesis pathway in Stevia rebaudiana (Bertoni)

    Microsoft Academic Search

    Hitesh Kumar; Kiran Kaul; Suphla Gupta-Bajpai; Vijay Kumar Kaul; Sanjay Kumar

    Stevia [Stevia rebuaidana (Bertoni); family: Asteraceae] is known to yield diterpenoid steviol glycosides (SGs), which are about 300 times sweeter than sugar. The present work analyzed the expression of various genes of the SGs biosynthesis pathway in different organs of the plant in relation to the SGs content. Of the various genes of the pathway, SrDXS, SrDXR, SrCPPS, SrKS, SrKO

  7. A monoterpene glucoside and three megastigmane glycosides from Juniperus communis var. depressa.

    PubMed

    Nakanishi, Tsutomu; Iida, Naoki; Inatomi, Yuka; Murata, Hiroko; Inada, Akira; Murata, Jin; Lang, Frank A; Iinuma, Munekazu; Tanaka, Toshiyuki; Sakagami, Yoshikazu

    2005-07-01

    A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2-4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated. PMID:15997135

  8. First Glycoside Hydrolase Family 2 Enzymes from Thermus antranikianii and Thermus brockianus with ?-Glucosidase Activity

    PubMed Central

    Schröder, Carola; Blank, Saskia; Antranikian, Garabed

    2015-01-01

    Two glycoside hydrolase encoding genes (tagh2 and tbgh2) were identified from different Thermus species using functional screening. Based on amino acid similarities, the enzymes were predicted to belong to glycoside hydrolase (GH) family 2. Surprisingly, both enzymes (TaGH2 and TbGH2) showed twofold higher activities for the hydrolysis of nitrophenol-linked ?-D-glucopyranoside than of -galactopyranoside. Specific activities of 3,966?U/mg for TaGH2 and 660?U/mg for TbGH2 were observed. In accordance, Km values for both enzymes were significantly lower when ?-D-glucopyranoside was used as substrate. Furthermore, TaGH2 was able to hydrolyze cellobiose. TaGH2 and TbGH2 exhibited highest activity at 95 and 90°C at pH 6.5. Both enzymes were extremely thermostable and showed thermal activation up to 250% relative activity at temperatures of 50 and 60°C. Especially, TaGH2 displayed high tolerance toward numerous metal ions (Cu2+, Co2+, Zn2+), which are known as glycoside hydrolase inhibitors. In this study, the first thermoactive GH family 2 enzymes with ?-glucosidase activity have been identified and characterized. The hydrolysis of cellobiose is a unique property of TaGH2 when compared to other enzymes of GH family 2. Our work contributes to a broader knowledge of substrate specificities in GH family 2. PMID:26090361

  9. Acylated flavonol glycosides with anti-complement activity from Persicaria lapathifolia.

    PubMed

    Park, S H; Oh, S R; Jung, K Y; Lee, I S; Ahn, K S; Kim, J H; Kim, Y S; Lee, J J; Lee, H K

    1999-10-01

    During a search for biologically active compounds from traditional medicines, a crude extract of Persicaria lapathifolia was found to have anti-complement activity. Bioassay-guided chromatographic separation of the active constituents led to the isolation of a new acylated kaempferol glycoside (1) and three known acylated quercetin glycosides (2-4). The structures of compounds 1-4 were characterized as kaempferol 3-O-beta-D-(6"-p-hydroxybenzoyl)-galactopyranoside, quercetin 3-O-beta-D-(6"-feruloyl)-galactopyranoside, quercetin 3-O-beta-D-(2"-galloyl)-rhamnopyranoside and quercetin 3-O-beta-D-(2"-galloyl)-glucopyranoside, respectively. Compounds 1-4 showed strong anti-complement activity (IC50 values of 4.3, 9.7, 3.9 and 7.6 x 10(-5) M, respectively) on the classical pathway of the complement. On the other hand, six isolated flavonol glycosides (5-10) did not show any activity on this system. PMID:10553645

  10. Variegatusides: New Non-Sulphated Triterpene Glycosides from the Sea Cucumber Stichopus variegates Semper

    PubMed Central

    Wang, Xiao-Hua; Zou, Zheng-Rong; Yi, Yang-Hua; Han, Hua; Li, Ling; Pan, Min-Xiang

    2014-01-01

    Four new triterpene glycosides, variegatusides C–F (1–4), together with three structurally known triterpene glycosides, variegatusides A and B (5, 6), and holothurin B (7), were isolated from the sea cucumber Stichopus variegates Semper (Holothuriidae), collected from the South China Sea. Their structures were elucidated on the basis of extensive spectral analysis (nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS)) and chemical evidence. Variegatusides C–F exhibit the same structural feature consisting of the presence of a 23-hydroxyl group at the holostane-type triterpene aglycone side chain. Variegatuside C (1) has a double bond (24, 25) in this same chain, while variegatuside D (2) exhibits a 8(9)-ene bond in the holostane-type triterpene aglycone, which has not been extracted from other sea cucumber species. Compound 4 is a native compound from the sea cucumber S. variegates Semper, which has been reported to be desacetylstichloroside B1. Except for holothurin B, these glycosides have no sulfate group in their sugar chain and show potent antifungal activities in vitro biotests. PMID:24699115

  11. A new phenolic constituent and a cyanogenic glycoside from Balanophora involucrata (Balanophoraceae).

    PubMed

    She, Gai-Mei; Zhang, Ying-Jun; Yang, Chong-Ren

    2013-06-01

    Balanophora involucrata HOOK.f. & THOMSON (Balanophoraceae) is a parasite plant often growing on the roots of leguminous plants. The whole herb has been used medicinally for the treatment of irregular menstruation, cough, hemoptysis, traumatic injury and bleeding, dizziness and gastralgia in Yunnan Province, China. The 2,2-diphenyl-2-picrylhydrazyl (DPPH) assay on the 60% aq. acetone extract of the fresh whole plant of B. involucrata showed considerable radical-scavenging activity (SC?? 15.3 ?g/ml). Further purification on the extract led to the isolation of one new phenolic glycoside, sieboldin-3'-ketocarboxylic acid (1), and one new cyanogenic glycoside, proacacipetalin 6'-O-?-D-glucopyranoside (2), together with 26 known compounds including three 4"-O-galloyl and 2",3"-O-(S)-hexahydroxydiphenoyl (HHDP) derivatives of dihydrochalcone glucosides, seven hydrolyzable tannins, and alkane glycosides. The cyanogenic compound isolated from the Balanophoraceae family for the first time might be a signal molecule between B. involucrata and its hosts. The free-radical-scavenging activity of the isolated compounds was also examined by DPPH assay. PMID:23776023

  12. Nickel-Catalyzed Proton-Deuterium Exchange (HDX) Procedures for Glycosidic Linkage Analysis of Complex Carbohydrates.

    PubMed

    Price, Neil P J; Hartman, Trina M; Vermillion, Karl E

    2015-07-21

    The structural analysis of complex carbohydrates typically requires the assignment of three parameters: monosaccharide composition, the position of glycosidic linkages between monosaccharides, and the position and nature of noncarbohydrate substituents. The glycosidic linkage positions are often determined by permethylation analysis, but this can be complicated by high viscosity or poor solubility, resulting in under-methylation. This is a drawback because an under-methylated position may be misinterpreted as the erroneous site of a linkage or substituent. Here, we describe an alternative approach to linkage analysis that makes use of a nonreversible deuterium exchange of C-H protons on the carbohydrate backbone. The exchange reaction is conducted in deuterated water catalyzed by Raney nickel, and results in the selective exchange of C-H protons adjacent to free hydroxyl groups. Hence, the position of the residual C-H protons is indicative of the position of glycosidic linkages or other substituents and can be readily assigned by heteronuclear single quantum coherence-nuclear magnetic resonance (HSQC-NMR) or, following suitable derivatization, by gas chromatography-mass spectroscopy (GC/MS) analysis. Moreover, because the only changes to the parent sugar are proton/deuterium exchanges, the composition and linkage analysis can be determined in a single step. PMID:26075577

  13. Influence of Extraction Methods on the Yield of Steviol Glycosides and Antioxidants in Stevia rebaudiana Extracts.

    PubMed

    Periche, Angela; Castelló, Maria Luisa; Heredia, Ana; Escriche, Isabel

    2015-06-01

    This study evaluated the application of ultrasound techniques and microwave energy, compared to conventional extraction methods (high temperatures at atmospheric pressure), for the solid-liquid extraction of steviol glycosides (sweeteners) and antioxidants (total phenols, flavonoids and antioxidant capacity) from dehydrated Stevia leaves. Different temperatures (from 50 to 100 °C), times (from 1 to 40 min) and microwave powers (1.98 and 3.30 W/g extract) were used. There was a great difference in the resulting yields according to the treatments applied. Steviol glycosides and antioxidants were negatively correlated; therefore, there is no single treatment suitable for obtaining the highest yield in both groups of compounds simultaneously. The greatest yield of steviol glycosides was obtained with microwave energy (3.30 W/g extract, 2 min), whereas, the conventional method (90 °C, 1 min) was the most suitable for antioxidant extraction. Consequently, the best process depends on the subsequent use (sweetener or antioxidant) of the aqueous extract of Stevia leaves. PMID:25726419

  14. Anti-inflammatory activity of methyl salicylate glycosides isolated from Gaultheria yunnanensis (Franch.) Rehder.

    PubMed

    Zhang, Dan; Liu, Rui; Sun, Lan; Huang, Chao; Wang, Chao; Zhang, Dong-Ming; Zhang, Tian-Tai; Du, Guan-Hua

    2011-01-01

    Gaultheria yunnanensis (Franch.) Rehder is a kind of traditional Chinese herbal medicine used for the treatments of rheumatoid arthritis, swelling and pain. Two methyl salicylate glycosides, namely methyl benzoate-2-O-?-D-xylopyranosyl(1-6)-O-?-D-gluco-pyranoside (J12122) and methyl benzoate-2-O-?-D-xylopyranosyl(1-2)[O-?-D-xylopyranosyl(1-6)]-O-?-D-glucopyranoside (J12123), are natural salicylic derivatives isolated from Gaultheria yunnanensis. In this study, we investigated the anti-inflammatory activity of J12122 and J12123 on LPS-induced RAW264.7 macrophage cells by measuring the production of pro-inflammatory cytokines, accumulation of nitric oxide (NO), and level of reactive oxygen species (ROS). The results showed that both methyl salicylate glycosides dose-dependently inhibited the production of tumor necrosis factor-? (TNF-?), interleukin-1? (IL-1?), and IL-6, respectively. Consistent with these observations, J12122 and J12123 significantly suppressed the accumulation of NO, with an inhibitory rate of 56.20% and 51.72% at 3.0 ?g/mL concentration, respectively. Furthermore, the two methyl salicylate glycosides reduced the level of ROS induced by LPS. These results showed that the isolated compounds possess anti-inflammatory properties through inhibition the production pro-inflammatory cytokines, NO, and ROS. PMID:21555977

  15. Reversible logic for supercomputing.

    SciTech Connect

    DeBenedictis, Erik P.

    2004-12-01

    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

  16. Reversible logic for supercomputing.

    SciTech Connect

    DeBenedictis, Erik P.

    2005-05-01

    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.

  17. 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

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

    2013-10-01

    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

  18. Optical isomer separation of flavanones and flavanone glycosides by nano-liquid chromatography using a phenyl-carbamate-propyl-beta-cyclodextrin chiral stationary phase.

    PubMed

    Si-Ahmed, Kahina; Tazerouti, Fairouz; Badjah-Hadj-Ahmed, Ahmed Y; Aturki, Zeineb; D'Orazio, Giovanni; Rocco, Anna; Fanali, Salvatore

    2010-02-12

    In this paper a phenyl-carbamate-propyl-beta-cyclodextrin stationary phase was employed for the enantioseparation of several flavonoids, including flavanones and methoxyflavanones by using nano-liquid chromatography (nano-LC). The same stationary phase was also used for the diastereoisomeric separation of two flavanone glycosides. The compounds: flavanone, 2'-hydroxyflavanone, 4'-hydroxyflavanone, 6-hydroxyflavanone, 7-hydroxyflavanone, 4'-methoxyflavanone, 6-methoxyflavanone, 7-methoxyflavanone, hesperetin, hesperidin, naringenin and naringin were studied using reversed, polar organic and normal elution modes. The effect of the nature and composition of the mobile phase (organic modifier type, buffer and water content in the reversed phase mode) on the enantioresolution (R(s)), retention factor (k) and enantioselectivity (alpha) were investigated. Baseline resolution of all studied flavonoids, with the exception of 2'-hydroxyflavanone and naringin, was achieved in reversed phase mode using a mixture of MeOH/H(2)O at different ratios as mobile phase. Good results, in terms of peak efficiency and short analysis time, were obtained adding 1% triethylammonium acetate pH 4.5 buffer to MeOH/H(2)O mixture. The separation of the studied compounds was also performed in polar organic mode. By using 100% of MeOH as mobile phase, the resolution was achieved for the studied analytes, except for 7-hydroxyflavanone, 2'-hydroxyflavanone, naringenin, hesperidin and naringin. Normal mode was tested employing a mixture of EtOH/hexane/TFA as mobile phase achieving the enantiomeric and diastereomeric separation of only hesperetin and hesperidin, respectively. The use of nano-LC technique for the resolution of flavanones optical isomers allowed to achieve good resolutions in shorter analysis time compared to the results reported in literature with conventional HPLC. PMID:19699481

  19. Cardiac glycoside activities link Na(+)/K(+) ATPase ion-transport to breast cancer cell migration via correlative SAR.

    PubMed

    Magpusao, Anniefer N; Omolloh, George; Johnson, Joshua; Gascón, José; Peczuh, Mark W; Fenteany, Gabriel

    2015-02-20

    The cardiac glycosides ouabain and digitoxin, established Na(+)/K(+) ATPase inhibitors, were found to inhibit MDA-MB-231 breast cancer cell migration through an unbiased chemical genetics screen for cell motility. The Na(+)/K(+) ATPase acts both as an ion-transporter and as a receptor for cardiac glycosides. To delineate which function is related to breast cancer cell migration, structure-activity relationship (SAR) profiles of cardiac glycosides were established at the cellular (cell migration inhibition), molecular (Na(+)/K(+) ATPase inhibition), and atomic (computational docking) levels. The SAR of cardiac glycosides and their analogs revealed a similar profile, a decrease in potency when the parent cardiac glycoside structure was modified, for each activity investigated. Since assays were done at the cellular, molecular, and atomic levels, correlation of SAR profiles across these multiple assays established links between cellular activity and specific protein-small molecule interactions. The observed antimigratory effects in breast cancer cells are directly related to the inhibition of Na(+)/K(+) transport. Specifically, the orientation of cardiac glycosides at the putative cation permeation path formed by transmembrane helices ?M1-M6 correlates with the Na(+) pump activity and cell migration. Other Na(+)/K(+) ATPase inhibitors that are structurally distinct from cardiac glycosides also exhibit antimigratory activity, corroborating the conclusion that the antiport function of Na(+)/K(+) ATPase and not the receptor function is important for supporting the motility of MDA-MB-231 breast cancer cells. Correlative SAR can establish new relationships between specific biochemical functions and higher-level cellular processes, particularly for proteins with multiple functions and small molecules with unknown or various modes of action. PMID:25334087

  20. Induction of phenolic glycosides by quaking aspen (Populus tremuloides) leaves in relation to extrafloral nectaries and epidermal leaf mining.

    PubMed

    Young, Brian; Wagner, Diane; Doak, Patricia; Clausen, Thomas

    2010-04-01

    We studied the effect of epidermal leaf mining on the leaf chemistry of quaking aspen, Populus tremuloides, during an outbreak of the aspen leaf miner, Phyllocnistis populiella, in the boreal forest of interior Alaska. Phyllocnistis populiella feeds on the epidermal cells of P. tremuloides leaves. Eleven days after the onset of leaf mining, concentrations of the phenolic glycosides tremulacin and salicortin were significantly higher in aspen leaves that had received natural levels of leaf mining than in leaves sprayed with insecticide to reduce mining damage. In a second experiment, we examined the time course of induction in more detail. The levels of foliar phenolic glycosides in naturally mined ramets increased relative to the levels in insecticide-treated ramets on the ninth day following the onset of leaf mining. Induction occurred while some leaf miner larvae were still feeding and when leaves had sustained mining over 5% of the leaf surface. Leaves with extrafloral nectaries (EFNs) had significantly higher constitutive and induced levels of phenolic glycosides than leaves lacking EFNs, but there was no difference in the ability of leaves with and without EFNs to induce phenolic glycosides in response to mining. Previous work showed that the extent of leaf mining damage was negatively related to the total foliar phenolic glycoside concentration, suggesting that phenolic glycosides deter or reduce mining damage. The results presented here demonstrate that induction of phenolic glycosides can be triggered by relatively small amounts of mining damage confined to the epidermal tissue, and that these changes in leaf chemistry occur while a subset of leaf miners are still feeding within the leaf. PMID:20354896

  1. On time reversal mirrors

    Microsoft Academic Search

    Albert C. Fannjiang

    2009-01-01

    The concept of time reversal (TR) of a scalar wave is reexamined from basic principles. Five different time-reversal mirrors (TRMs) are introduced and their relations are analyzed. For the boundary behavior, it is shown that for a paraxial wave only the monopole TR scheme satisfies the exact boundary condition while for the spherical wave only the MD-mode TR scheme satisfies

  2. Ultrasonic Time Reversal Mirrors

    NASA Astrophysics Data System (ADS)

    Fink, Mathias; Montaldo, Gabriel; Tanter, Mickael

    2004-11-01

    For more than ten years, time reversal techniques have been developed in many different fields of applications including detection of defects in solids, underwater acoustics, room acoustics and also ultrasound medical imaging and therapy. The essential property that makes time reversed acoustics possible is that the underlying physical process of wave propagation would be unchanged if time were reversed. In a non dissipative medium, the equations governing the waves guarantee that for every burst of sound that diverges from a source there exists in theory a set of waves that would precisely retrace the path of the sound back to the source. If the source is pointlike, this allows focusing back on the source whatever the medium complexity. For this reason, time reversal represents a very powerful adaptive focusing technique for complex media. The generation of this reconverging wave can be achieved by using Time Reversal Mirrors (TRM). It is made of arrays of ultrasonic reversible piezoelectric transducers that can record the wavefield coming from the sources and send back its time-reversed version in the medium. It relies on the use of fully programmable multi-channel electronics. In this paper we present some applications of iterative time reversal mirrors to target detection in medical applications.

  3. MIMO time reversal communications

    Microsoft Academic Search

    Hee-chun Song; William S. Hodgkiss; William A. Kuperman

    2007-01-01

    A time reversal mirror (TRM) exploits spatial diversity to achieve spatial and temporal focusing, a useful property for communications in an environment with significant multipath. Temporal focusing (pulse compression) mitigates intersymbol interference (ISI) while spatial focusing enables a straightforward extension to multiple- input\\/multiple-output (MIMO) communications. Furthermore, the time reversal process can be combined with adaptive channel equalization to remove the

  4. Geomagnetism II: Magnetic Reversals

    NSDL National Science Digital Library

    2012-08-03

    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.

  5. Reversibility of laser filamentation

    E-print Network

    Nicolas Berti; Wahb Ettoumi; Jérôme Kasparian; Jean-Pierre Wolf

    2014-09-03

    We investigate the reversibility of laser filamentation, a self-sustained, non-linear propagation regime including dissipation and time-retarded effects. We show that even losses related to ionization marginally affect the possibility of reverse propagating ultrashort pulses back to the initial conditions, although they make it prone to finite-distance blow-up susceptible to prevent backward propagation.

  6. Synthesis of dopamine and L-DOPA-alpha-glycosides by reaction with cyclomaltohexaose catalyzed by cyclomaltodextrin glucanyltransferase.

    PubMed

    Yoon, Seung-Heon; Bruce Fulton, D; Robyt, John F

    2009-11-23

    Dopamine-HCl and L-DOPA-alpha-glycosides were prepared by reaction with cyclomaltohexaose, catalyzed by Bacillus macerans cyclomaltodextrin glucanyltransferase. The reaction gave maltodextrins attached to dopamine and L-DOPA; the maltodextrins were trimmed by reactions with glucoamylase and beta-amylase to produce alpha-glucosyl- and alpha-maltosyl-glycosides, respectively. The glucoamylase- or beta-amylase-treated dopamine- and L-DOPA-alpha-glycosides were fractionated and purified by BioGel P-2 gel-filtration column chromatography and preparative descending paper chromatography. Analysis by MALDI-TOF mass spectrometry and one- and two-dimensional NMR showed that the purified glycosides of dopamine and L-DOPA were glycosylated at the hydroxyl groups of positions 3 and 4 of the catechol ring. The major product was found to be 4-O-alpha-glycopyranosyl L-DOPA, and it was shown to be more resistant to oxidative tolerance experiments, involving hydrogen peroxide and ferrous ion, than L-DOPA. L-DOPA-alpha-glycosides are possibly more effective substitutes for L-DOPA in treating Parkinson's disease in that they are more resistant to oxidation and methylation, which renders L-DOPA ineffective and deleterious. PMID:19793583

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

    PubMed

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

    2011-09-01

    Cardiac glycosides from fresh leaves of Nerium indicum were evaluated for its molluscicidal activity against Pomacea canaliculata (golden apple snail: GAS) under laboratory conditions. The results showed that LC(50) value of cardiac glycosides against GAS was time dependent and the LC(50) value at 96 h was as low as 3.71 mg/L, which was comparable with that of metaldehyde at 72 h (3.88 mg/L). These results indicate that cardiac glycosides could be an effective molluscicide against GAS. The toxicological mechanism of cardiac glucosides on GAS was also evaluated through changes of selected biochemical parameters, including cholinesterase (ChE) and esterase (EST) activities, glycogen and protein contents in hepatopancreas tissues of GAS. Exposure to sublethal concentrations of cardiac glycosides, GAS showed lower activities of EST isozyme in the later stages of the exposure period as well as drastically decreased glycogen content, although total protein content was not affected at the end of 24 and 48 h followed by a significant depletion at the end of 72 and 96 h. The initial increase followed by a decline of ChE activity was also observed during the experiment. These results suggest that cardiac glycosides seriously impair normal physiological metabolism, resulting in fatal alterations in major biochemical constituents of hepatopancreas tissues of P. canaliculata. PMID:21843803

  8. Effects of pregnane glycosides on food intake depend on stimulation of the melanocortin pathway and BDNF in an animal model.

    PubMed

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

    2013-02-27

    Pregnane glycosides appear to modulate food intake by possibly affecting the hypothalamic feeding circuits; however, the mechanisms of the appetite-regulating effect of pregnane glycosides remain obscure. Here, we show that pregnane glycoside-enriched extracts from swamp milkweed Asclepias incarnata at 25-100 mg/kg daily attenuated food intake (up to 47.1 ± 8.5% less than controls) and body weight gain in rats (10% for males and 9% for females, respectively) by activating melanocortin signaling and inhibiting gastric emptying. The major milkweed pregnane glycoside, ikemagenin, exerted its appetite-regulating effect by decreasing levels of agouti-related protein (0.6-fold) but not NPY satiety peptides. Ikemagenin treatment also increased secretion of brain-derived neurotropic factor (BDNF) downstream of melanocortin receptors in the hypothalamus (1.4-fold) and in the C6 rat glioma cell culture in vitro (up to 6-fold). These results support the multimodal effects of pregnane glycosides on feeding regulation, which depends on the activity of the melanocortin signaling pathway and BDNF. PMID:23308358

  9. Effects of Pregnane Glycosides on Food Intake Depend on Stimulation of the Melanocortin Pathway and BDNF in an Animal Model

    PubMed Central

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

    2013-01-01

    Pregnane glycosides appear to modulate food intake by possibly affecting the hypothalamic feeding circuits; however, the mechanisms of the appetite-regulating effect of pregnane glycosides remain obscure. Here, we show that pregnane glycoside-enriched extracts from swamp milkweed Asclepias incarnata at 25–100 mg/kg daily attenuated food intake (up to 47.1 ± 8.5% less than controls) and body weight gain in rats (10% for males and 9% for females, respectively) by activating melanocortin signaling and inhibiting gastric emptying. The major milkweed pregnane glycoside, ikemagenin, exerted its appetite-regulating effect by decreasing levels of agouti-related protein (0.6-fold) but not NPY satiety peptides. Ikemagenin treatment also increased secretion of brain-derived neurotropic factor (BDNF) downstream of melanocortin receptors in the hypothalamus (1.4-fold) and in the C6 rat glioma cell culture in vitro (up to 6-fold). These results support the multimodal effects of pregnane glycosides on feeding regulation, which depends on the activity of the melanocortin signaling pathway and BDNF. PMID:23308358

  10. Norsesquiterpene glycosides in bracken ferns (Pteridium esculentum and Pteridium aquilinum subsp. wightianum) from Eastern Australia: reassessed poisoning risk to animals.

    PubMed

    Fletcher, Mary T; Brock, Ian J; Reichmann, Keith G; McKenzie, Ross A; Blaney, Barry J

    2011-05-11

    Austral bracken Pteridium esculentum contains three unstable norsesquiterpene glycosides: ptaquiloside, ptesculentoside, and caudatoside, in variable proportions. The concentration of each of the glycosides was determined in this study as their respective degradation products, pterosin B, pterosin G and pterosin A, by HPLC-UV analysis. Samples of P. esculentum collected from six sites in eastern Australia contained up to 17 mg of total glycoside/g DW, with both ptaquiloside and ptesculentoside present as major components accompanied by smaller amounts of caudatoside. Ratios of ptaquiloside to ptesculentoside varied from 1:3 to 4:3, but in all Australian samples ptesculentoside was a significant component. This profile differed substantially from that of P. esculentum from New Zealand, which contained only small amounts of both ptesculentoside and caudatoside, with ptaquiloside as the dominant component. A similar profile with ptaquiloside as the dominant glycoside was obtained for Pteridium aquilinum subsp. wightianum (previously P. revolutum ) from northern Queensland and also P. aquilinum from European sources. Ptesculentoside has chemical reactivity similar to that of ptaquiloside and presumably biological activity similar to that of this potent carcinogen. The presence of this additional reactive glycoside in Australian P. esculentum implies greater toxicity for consuming animals than previously estimated from ptaquiloside content alone. PMID:21456622

  11. Enriching Reverse Engineering with Annotations

    E-print Network

    Nierstrasz, Oscar

    Enriching Reverse Engineering with Annotations Masterarbeit der Philosophisch Successful reverse engineering needs to take into account human knowledge about architecture, about features to the automatically reverse engineered model and should be taken into account by analyses. Typically, when we want

  12. Introduction Reverse Engineering MIFARE Classic

    E-print Network

    Garcia, Flavio D.

    Introduction Reverse Engineering MIFARE Classic Cryptanalysis of MIFARE Classic Conclusions MIFARE Classic #12;Introduction Reverse Engineering MIFARE Classic Cryptanalysis of MIFARE Classic Conclusions Outline 1 Introduction Timeline RFID MIFARE 2 Reverse Engineering MIFARE Classic Characteristics

  13. Induction of cytotoxic and genotoxic responses by natural and novel quercetin glycosides.

    PubMed

    Engen, Anya; Maeda, Junko; Wozniak, David E; Brents, Colleen A; Bell, Justin J; Uesaka, Mitsuru; Aizawa, Yasushi; Kato, Takamitsu A

    2015-06-01

    The flavonoids quercetin, and its natural glycosides isoquercetin and rutin, are phytochemicals commonly consumed in plant-derived foods. Semi-synthetic water-soluble isoquercetin and rutin glycosides, maltooligosyl isoquercetin, monoglucosyl rutin and maltooligosyl rutin were developed by synthetic glycosylation to overcome solubility challenges for improved incorporation in food and medicinal applications. Quercetin and its natural glycosides are known to induce genetic instability and decrease cell proliferation. Using a system of Chinese hamster ovary (CHO) cells, this study examined the differences in cytotoxic and genotoxic responses induced by natural and synthetic flavonoids. Bioactivity evaluations using poly(ADP-ribose) polymerase (PARP) ELISA showed that the synthetic flavonoids were less effective in inhibiting PARP than the natural flavonoids, where PARP inhibitory effects decreased with glycosylation of flavonoids. In the genotoxic studies, treatments with flavonoids at a concentration range of 0.2?M-1mM induced significant frequencies of sister chromatid exchange (SCE) and micronuclei in CHO cells compared to spontaneous occurrences. The synthetic flavonoids monoglucosyl rutin and maltooligosyl rutin induced less genotoxic effects than the natural flavonoids. However, maltooligosyl isoquercetin induced similar responses as isoquercetin and rutin. The growth inhibition studies showed glycosylation dependent cytotoxicity in natural flavonoids. The quercetin aglycone exhibited the highest toxicity out of all the flavonoids studied. Differences in growth inhibition were not observed between the synthetic flavonoids, maltooligosyl isoquercetin and monoglucosyl rutin, and natural isoquercetin and rutin, respectively. Maltooligosyl rutin induced less cytotoxicity than rutin and monoglucosyl rutin. Our in vitro studies demonstrated that the synthetic flavonoids generally induced less genotoxic responses than their natural counterparts. PMID:26046972

  14. Identification, quantification and antioxidant activity of acylated flavonol glycosides from sea buckthorn (Hippophae rhamnoides ssp. sinensis).

    PubMed

    Chen, Chu; Xu, Xue-Min; Chen, Yang; Yu, Meng-Yao; Wen, Fei-Yan; Zhang, Hao

    2013-12-01

    A novel acylated flavonol glycoside: isorhamnetin (3-O-[(6-O-E-sinapoyl)-?-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

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

    PubMed Central

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

    2008-01-01

    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 1.6Ĺ 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

  16. Tripterygium glycosides induce premature ovarian failure in rats by promoting p53 phosphorylation and activating the serine/threonine kinase 11-p53-p21 signaling pathway

    PubMed Central

    LIU, TE; ZHANG, LINA; WANG, SUWEI; CHEN, CHUAN; ZHENG, JIN

    2015-01-01

    Premature ovarian failure (POF) is a typical pathological disease of the reproductive system in aging females. Infection, inflammation, immune abnormalities, genetic mutation, radiotherapy and chemotherapy can cause POF. Tripterygium glycosides (TGs) are a component extracted from the Chinese herb Tripterygium wilfordii Hook. f., also known as Huangteng. Although TGs have been used to treat various diseases, drug resistance and toxicity can affect patients. The aim of the present study was to investigate the mechanism of TG-induced POF in rats. The rats were treated with different concentrations of TG, and pathology assays showed that the TG-induced POF was predominantly composed of interstitial cells in a fibrous matrix with a reduced number of follicles at each stage and an increased number of collapsed oocytes. Furthermore, reverse transcription-quantitative polymerase chain reaction (PCR) and immunohistochemistry assays indicated that the expression levels of serine/threonine kinase 11 (Stk11), p53 p21 and activated caspase-3 were elevated significantly in the TG-treated groups. Serine 15 phosphorylation of p53 was also enhanced significantly in the TG-treated groups. In addition, a chromatin immunoprecipitation-PCR assay revealed that the TGs induced p53 activation and enhanced the transcription of p21. In conclusion, TGs induce apoptosis and necrosis in rat ovarian tissues, as well as POF, via p53 phosphorylation and activation of the Stk11-p53-p21 signaling pathway. PMID:26170905

  17. Effects of hesperidin, a flavanone glycoside interaction on the conformation, stability, and aggregation of lysozyme: multispectroscopic and molecular dynamic simulation studies?

    PubMed

    Ratnaparkhi, Aditi; Muthu, Shivani A; Shiriskar, Sonali M; Pissurlenkar, Raghuvir R S; Choudhary, Sinjan; Ahmad, Basir

    2015-09-01

    Hesperidin (HESP), a flavanone glycoside, shows high antioxidant properties and posses ability to go through the blood-brain barrier. Therefore, it could be a potential drug molecule against aggregation based diseases such as Alzheimer's, Parkinson's, and systemic amyloidoses. In this work, we investigated the potential of HESP to interact with hen egg-white lysozyme (HEWL) monomer and prevent its aggregation. The HESP-HEWL binding studies were performed using a fluorescence quenching technique, molecular docking and molecular dynamics simulations. We found a strong interaction of HESP with the lysozyme monomer (Ka, ~ 5 × 10(4) M(-1)) mainly through hydrogen bonding, water bridges, and hydrophobic interactions. We showed that HESP molecule spanned the highly aggregation prone region (amino acid residues 48-101) of HEWL and prevented its fibrillar aggregation. Further, we found that HESP binding completely inhibited amorphous aggregation of the protein induced by disulfide-reducing agent tries-(2-carboxyethyl) phosphine. Conformational and stability studies as followed by various tertiary and secondary structure probes revealed that HESP binding only marginally affected the lysozyme monomer conformation and increased both stability and reversibility of the protein against thermal denaturation. Future studies should investigate detail effects of HESP on solvent dynamics, structure, and toxicity of various aggregates. The answers to these questions will not only target the basic sciences, but also have application in biomedical and biotechnological sciences. PMID:25301518

  18. In silico analysis and molecular docking studies of potential angiotensin-converting enzyme inhibitor using quercetin glycosides.

    PubMed

    Muhammad, Syed Aun; Fatima, Nighat

    2015-05-01

    The purpose of this study was to analyze the inhibitory action of quercetin glycosides by computational docking studies. For this, natural metabolite quercetin glycosides isolated from buckwheat and onions were used as ligand for molecular interaction. The crystallographic structure of molecular target angiotensin-converting enzyme (ACE) (peptidyl-dipeptidase A) was obtained from PDB database (PDB ID: 1O86). Enalapril, a well-known brand of ACE inhibitor was taken as the standard for comparative analysis. Computational docking analysis was performed using PyRx, AutoDock Vina option based on scoring functions. The quercetin showed optimum binding affinity with a molecular target (angiotensin-converting-enzyme) with the binding energy of -8.5 kcal/mol as compared to the standard (-7.0 kcal/mol). These results indicated that quercetin glycosides could be one of the potential ligands to treat hypertension, myocardial infarction, and congestive heart failure. PMID:26109757

  19. In silico analysis and molecular docking studies of potential angiotensin-converting enzyme inhibitor using quercetin glycosides

    PubMed Central

    Muhammad, Syed Aun; Fatima, Nighat

    2015-01-01

    The purpose of this study was to analyze the inhibitory action of quercetin glycosides by computational docking studies. For this, natural metabolite quercetin glycosides isolated from buckwheat and onions were used as ligand for molecular interaction. The crystallographic structure of molecular target angiotensin-converting enzyme (ACE) (peptidyl-dipeptidase A) was obtained from PDB database (PDB ID: 1O86). Enalapril, a well-known brand of ACE inhibitor was taken as the standard for comparative analysis. Computational docking analysis was performed using PyRx, AutoDock Vina option based on scoring functions. The quercetin showed optimum binding affinity with a molecular target (angiotensin-converting-enzyme) with the binding energy of ?8.5 kcal/mol as compared to the standard (?7.0 kcal/mol). These results indicated that quercetin glycosides could be one of the potential ligands to treat hypertension, myocardial infarction, and congestive heart failure. PMID:26109757

  20. A new ent-kaurane diterpenoid glycoside from Isodon japonica var. glaucocalyx.

    PubMed

    Xiang, Zhao-Bao; Wang, Guang-Li; Huang, Lan-Zhi; Heng, Lin-Sen; Li, Xiao-Hui

    2013-01-01

    A new ent-kaurane diterpenoid glycoside (1), named glaucocalyxin G, has been isolated from the n-butanol-soluble fraction of the dried whole plants of Isodon japonica var. glaucocalyx along with two known compounds, namely arjunglucoside (2) and kaempferol-3-O-rutinoside (3). The structures of the isolated compounds were assigned on the basis of their (1)H and (13)C NMR spectra including two-dimensional NMR techniques such as HMQC, HMBC, and NOESY experiments and comparison with the literature data. PMID:23614395

  1. A novel sulphur glycoside from the seeds of Descurainia sophia (L.).

    PubMed

    Sun, K; Li, X; Liu, J-M; Wang, J-H; Li, W; Sha, Y

    2005-12-01

    A new sulphur glycoside, named descurainoside (1), and the known compound sinapic acid (2) have been isolated from the seeds of Descurainia sophia (L.) Webb ex Prantl. The structure of 1 has been identified as (1R,6S,8R,9S,10S)-9,10-dihydroxy-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-8-(hydroxymethyl)-2,7-dioxa-5-thiabicyclo[4.4.0]decan-3-one by means of physico-chemical properties and spectroscopic methods (1D and 2D NMR, HRMS, ESI-MS). PMID:16308204

  2. A novel sulphur glycoside from the seeds of Descurainia sophia (L.)

    Microsoft Academic Search

    K. Sun; X. Li; J.-M. Liu; J.-H. Wang; W. Li; Y. Sha

    2005-01-01

    A new sulphur glycoside, named descurainoside (1), and the known compound sinapic acid (2) have been isolated from the seeds of Descurainia sophia (L.) Webb ex Prantl. The structure of 1 has been identified as (1R,6S,8R,9S,10S)-9,10-dihydroxy-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-8-(hydroxymethyl)-2,7-dioxa-5-thiabicyclo[4.4.0]decan-3-one by means of physico-chemical properties and spectroscopic methods (1D and 2D NMR, HRMS, ESI-MS).

  3. A new benzofuran glycoside and indole alkaloids from a sponge-associated rare actinomycete, Amycolatopsis sp.

    PubMed

    Kwon, Yun; Kim, Seong-Hwan; Shin, Yoonho; Bae, Munhyung; Kim, Byung-Yong; Lee, Sang Kook; Oh, Ki-Bong; Shin, Jongheon; Oh, Dong-Chan

    2014-04-01

    Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 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

  4. Two new triterpene glycosides from the Vietnamese sea cucumber Holothuria scabra.

    PubMed

    Dang, Nguyen Hai; Thanh, Nguyen Van; Kiem, Phan Van; Huong, Le Mai; Minh, Chau Van; Kim, Young Ho

    2007-11-01

    Two new triterpene glycosides, namely holothurin A3 (1) and A4 (2) were isolated from the methanol extract of the sea cucumber, Holothuria scabra, with their structures elucidated from the spectroscopic evidence (1D NMR, 2D NMR, ESI-MS and HRESI-MS). Compounds 1 and 2 were found to be strongly cytotoxic to both cancer cell lines, KB and Hep-G2, with 50% inhibitory concentrations (IC50) of 0.87 and 0.32 microg/mL (for compound 1) and of 1.12 and 0.57 microg/mL (for compound 2), respectively. PMID:18087805

  5. A new monoterpenoid glycoside from Myrica esculenta and the inhibition of angiotensin I-converting enzyme.

    PubMed

    Nguyen, Xuan Nhiem; Phan, Van Kiem; Chau, Van Minh; Bui, Huu Tai; Nguyen, Xuan Cuong; Vu, Kim Thu; Hoang, Le Tuan Anh; Jo, Sung-Hoon; Jang, Hae-Dong; Kwon, Young-In; Kim, Young Ho

    2010-10-01

    One new monoterpenoid glycoside, myresculoside (1), and eleven known compounds, were isolated from methanol extract of Myrica esculenta leaves by repeated column chromatography. The effects of these compounds on angiotensin I-converting enzyme (ACE) inhibition were investigated. Compounds 3 and 4 showed the most potent ACE inhibition with rates of 29.97% and 25.63% at concentration of 100 µM, respectively. Compounds 5, 6, and 11 showed weak activity with inhibitory rates of 0.07-1.41% at concentration of 100 µM. PMID:20930414

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

    PubMed

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

    2014-01-01

    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

  7. Effect of Morinda citrifolia fruit extract and its iridoid glycosides on blood fluidity.

    PubMed

    Murata, Kazuya; Abe, Yumi; Futamura-Masuda, Megumi; Uwaya, Akemi; Isami, Fumiyuki; Deng, Shixin; Matsuda, Hideaki

    2014-07-01

    The aim of this study was to investigate the effect of Morinda citrifolia fruit on blood fluidity. M. citrifolia fruit extract (MCF-ext) was investigated for its influence on blood aggregation and fibrinolysis. MCF-ext inhibited polybrene-induced erythrocyte aggregation and thrombin activity. The fibrinolytic activity of MCF-ext, in the euglobulin lysis time test and fibrin plate assay, is reported here for the first time. One of the active compounds was an iridoid glycoside, asperulosidic acid. The results indicated that MCF-ext is a potentially useful health food which is capable of improving blood flow and preventing lifestyle-related diseases. PMID:24604344

  8. Quantification of the flavonoid glycosides in Passiflora incarnata by capillary electrophoresis.

    PubMed

    Marchart, Elke; Krenn, Liselotte; Kopp, Brigitte

    2003-05-01

    Capillary electrophoresis has been applied for the separation and quantification of the flavonoids in Passiflorae herba. Separations were performed using 25 mM sodium borate with 20 % methanol (pH 9.5). For the quantification quercetin 3-O-arabinoside was used as internal standard. The method was applied to the determination of the flavonoid glycosides in 10 different commercial samples of the drug and showed similar flavonoid patterns, but differences concerning the single and total amounts of flavonoids. The total flavonoid contents determined with the new method correlated satisfactorily with those achieved by the spectrophotometric assay according to the European Pharmacopoeia. PMID:12802728

  9. A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.

    PubMed Central

    Kwon, Yun; Kim, Seong-Hwan; Shin, Yoonho; Bae, Munhyung; Kim, Byung-Yong; Lee, Sang Kook; Oh, Ki-Bong; Shin, Jongheon; Oh, Dong-Chan

    2014-01-01

    Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 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

  10. Octopus glycosides: multivalent molecular platforms for testing carbohydrate recognition and bacterial adhesion.

    PubMed

    Lindhorst, Thisbe K; Dubber, Michael

    2015-02-11

    Multivalency of carbohydrate-protein interactions is critical for cell adhesion, including attachment of bacteria to their host cells. To investigate specific parameters of multivalency effects, a variety of multivalent glycoconjugates has been designed according to different mimetic approaches. Some 15 years ago, carbohydrates were elaborated as multivalent scaffold molecules for the preparation of carbohydrate-centred 'octopus glycosides' as well as of other carbohydrate-centred glycoconjugates. The beginning of this research is reported from a historical perspective and a selection of interesting applications is highlighted. PMID:25104394

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

    PubMed

    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

    2015-01-01

    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

  12. A new acylated quercetin glycoside from the leaves of Stevia rebaudiana Bertoni

    Microsoft Academic Search

    Jun Li; Hua Jiang; Renbing Shi

    2009-01-01

    A new acylated quercetin glycoside quercetin-3-O-(4??-O-trans-caffeoyl)-?-L-rhamnopyranosyl-(1 ? 6)-?-D-galacopyranoside (1), along with luteolin (2), quercetin (3), luteolin-7-O-?-D-glucoside (4), apigenin-7-O-?-D-glucoside (5), quercitrin (6), quercetin-3-O-?-D-arabinoside (7) and 4,5-di-O-caffeoyl quinic acid (8) have been isolated from the leaves of Stevia rebaudiana Bertoni. The structures of these compounds were determined by spectroscopic methods (H- and C-NMR, IR and MS) and by 2D-NMR experiments.

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

    PubMed Central

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

    1966-01-01

    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

  14. One step purification of flavanone glycosides from Poncirus trifoliata by centrifugal partition chromatography.

    PubMed

    Kim, Chul Young; Lee, Hee Ju; Lee, Mi Kyeong; Ahn, Mi-Jeong; Kim, Jinwoong

    2007-11-01

    Flavanone glycosides were successfully separated from the crude extract of Poncirus trifoliata by preparative centrifugal partition chromatography with a two-phase solvent system composed of ethyl acetate-acetonitrile-water (3:2:5, v/v/v). Naringin (50.0 mg), neoponcirin (16.8 mg), and poncirin (71.9 mg) were purified from the 524 mg crude extract in only one step. The purities of the isolated compounds were determined to be over 90% by HPLC analysis and their structures were elucidated by (1)H NMR, (13)C NMR, and ESI-MS. PMID:17823893

  15. Studies on the phenylethanoid glycosides with anti-complement activity from Paulownia tomentosa var. tomentosa wood

    Microsoft Academic Search

    Chuan-Ling Si; Xiao-Juan Deng; Zhong Liu; Jin-Kyu Kim; Young-Soo Bae

    2008-01-01

    Four epimeric phenylethanoid glycosides, including a new one, R,S-?-ethoxy-?-(3,4-dihydroxyphenyl)-ethyl-O-?-l-rhamnopyranosyl(1 ? 3)-?-d-(6-O-E-caffeoyl)-glucopyranoside named isoilicifolioside A (1), and three known compounds, ilicifolioside A (2), campneoside II (3), and isocampneoside II (4), were isolated from Paulownia tomentosa var. tomentosa wood. The structures of the four compounds were elucidated by the interpretation of 1D and 2D NMR and MS spectra. This is the first report of

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

    Microsoft Academic Search

    Hidenori Tozuka; Michikazu Ota; Hisayoshi Kofujita; Kouetsu Takahashi

    2005-01-01

    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

  17. Two new ionone glycosides from the roots of Rehmannia glutinosa Libosch.

    PubMed

    Feng, Wei-Sheng; Li, Meng; Zheng, Xiao-Ke; Zhang, Na; Song, Kai; Wang, Jian-Chao; Kuang, Hai-Xue

    2015-01-01

    Two new ionone glycosides, named frehmaglutoside G (1) and frehmaglutoside H (2), together with six known compounds, rehmapicroside (3), sec-hydroxyaeginetic acid (4), dihydroxy-?-ionone (5), trihydroxy-?-ionone (6), rehmaionoside A (7) and rehmaionoside C (8), were isolated from the 95% EtOH extract of the dried roots of Rehmannia glutinosa Libosch. Their structures were determined on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D and 2D NMR ((1)H-(1)H COSY, HSQC, HMBC and NOESY) methods. The absolute configurations were confirmed via the circular dichroism spectra. PMID:25232801

  18. Two new steroidal glycosides isolated from the aerial part of Solanum torvum Swartz.

    PubMed

    Shu, Weihu; Wu, Chun; Zhang, Ying; Ye, Wen-Cai; Zhou, Guangxiong

    2013-01-01

    One novel C-22 steroidal lactone saponin, namely solanolactoside C (1), and one new spirostanol glycoside, namely torvoside Q (2), were isolated from the ethanolic extract of aerial parts of Solanum torvum Swartz. The structures of 1 and 2 were determined by extensive NMR experiments including (1)H NMR, (13)C NMR, DEPT, (1)H-(1)H COSY, HSQC, HMBC and ROESY and HRESIMS to be solanolide 6-O-?-d-quinovopyranoside and neochlorogenin 6-O-[?-d-xylopyranosyl-(1 ? 3)-?-d-glucopyranoside], respectively. PMID:23815408

  19. Alkyl-imidazolium glycosides: non-ionic-cationic hybrid surfactants from renewable resources.

    PubMed

    Salman, Abbas Abdulameer; Tabandeh, Mojtaba; Heidelberg, Thorsten; Hussen, Rusnah Syahila Duali; Ali, Hapipah Mohd

    2015-08-14

    A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures. PMID:26000863

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

    PubMed

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

    1991-06-01

    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

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

    PubMed

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

    2006-04-01

    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

  2. 27-Nor-triterpenoid glycosides from the barks of Zygophyllum fabago L

    Microsoft Academic Search

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

    2007-01-01

    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.

  3. 27-nor-triterpenoid glycosides from the barks of Zygophyllum fabago L.

    PubMed

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

    2007-01-01

    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

  4. An HPLC-PAD method to analyse flavonoid glycosides and styrylpyrones from Cryptocarya species (Lauraceae).

    PubMed

    Nehme, Cláudia J; Bastos, Wagner L; de Araújo, Adelson J; Cavalheiro, Alberto J

    2005-01-01

    An HPLC-PAD method has been developed in order to evaluate simultaneously the main secondary metabolites, flavonoid glycosides and styrylpyrones, of leaves of Cryptocarya moschata. The sample preparation, consisting of extraction, liquid-liquid extraction and centrifugation, requires minimum sample manipulation but produces high yields with reproducibility, selectivity and simplicity. HPLC on a C18 column presents each class of metabolites grouped and with good resolution of the main compounds. The experimental conditions can be used to study inter- and intra-specific variability of secondary metabolites in Cryptocarya spp. PMID:15881116

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

    PubMed

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

    2012-01-01

    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

  6. Identification of flavonoid glycosides in Rosa chinensis flowers by liquid chromatography-tandem mass spectrometry in combination with ąłC nuclear magnetic resonance.

    PubMed

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

    2012-08-01

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

  7. The genetic basis for variation in the concentration of phenolic glycosides in Salix sericea: Clonal variation and sex-based differences

    Microsoft Academic Search

    COLIN M. NICHOLS-ORIANS; ROBERT S. FRITZ; THOMAS P. CLAUSEN

    1993-01-01

    Many members of the Salicaceae produce phenolic glycosides, and the concentrations of these are known to vary among plants. We determined whether the concentration of two phenolic glycosides, salicortin and 2'-cinnamoyl salicortin, varied among clones of Salix sericea and whether this variation was due to the sex of the plant. We tested 16 clones, seven male and nine female, for

  8. Phenylvaleric Acid and Flavonoid Glycosides from Polygonum salicifolium Ihsan Calis,*, Ayse Kuruuzum, L. O mur Demirezer, Otto Sticher, Walter Ganci, and Peter Ruedi

    E-print Network

    Rüedi, Peter

    Phenylvaleric Acid and Flavonoid Glycosides from Polygonum salicifolium Ihsan Calis,*, Ayse Kuruu-hydroxy-3,6-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol- 3-O- -D-glucopyranoside () astragalin) (4), kaempferol-3-O- -D-galactopyranoside (5), quercetin-3-O- - D

  9. Effects of Phenolic Glycosides and Protein on Gypsy Moth (Lepidoptera: Lymantriidae) and Forest Tent Caterpillar (Lepidoptera: Lasiocampidae) Performance and Detoxication Activities

    Microsoft Academic Search

    Jocelyn D. C. Hemming; Richard L. Lindroth

    2000-01-01

    Levels of phenolic glycosides and protein influence the quality of aspen leaves to herbivorous insects, and vary in relation to genetic and environmental factors. This research was conducted to assess the independent and interactive effects of phenolic glycosides and protein on the performance and detoxication enzyme activities of gypsy moths, Lymantria dispar (L.), and forest tent caterpillars, Malacosoma disstria Hubner.

  10. Indonesian medicinal plants. XIX. 1) Chemical structures of four additional resin-glycosides, mammosides A, B, H1, and H2, from the tuber of Merremia mammosa (Convolvulaceae).

    PubMed

    Kitagawa, I; Ohashi, K; Baek, N I; Sakagami, M; Yoshikawa, M; Shibuya, H

    1997-05-01

    Four new resin-glycosides, named mammosides A (10), B (11), H1 (12), and H2 (13), were isolated from the tuber of Merremia mammosa (Convolvulaceae), a Jamu raw material. Their chemical structures have been elucidated on the bases of chemical and physicochemical evidence, including synthesis of a glycosidic acid designated as mammoside I. PMID:9178519

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

    Microsoft Academic Search

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

    2000-01-01

    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

  12. Flavonoid Glycosides and Naphthodianthrones in the Sawfly Tenthredo zonula and its Host-Plants, Hypericum perforatum and H. hirsutum

    PubMed Central

    2012-01-01

    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

  13. Flavonoid glycosides and naphthodianthrones in the sawfly Tenthredo zonula and its host-plants, Hypericum perforatum and H. hirsutum.

    PubMed

    Crockett, Sara L; Boevé, Jean-Luc

    2011-09-01

    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

  14. Apparent lack of pharmacological effect of steviol glycosides used as sweeteners in humans. A pilot study of repeated exposures in some normotensive and hypotensive individuals and in Type 1 and Type 2 diabetics

    Microsoft Academic Search

    Luis A. Barriocanal; Mafalda Palacios; Gilda Benitez; Sussam Benitez; Jorge T. Jimenez; Nora Jimenez; Vicenta Rojas

    2008-01-01

    Steviol glycosides, isolated from the plant Stevia rebaudiana (Bertoni) Bertoni, have been used as safe sweetening agents for more than 30 years. Beneficial effects of high doses of steviol glycosides on hyperglycemia and hypertension have been previously described when these abnormalities are present. This study was designed to evaluate the effects of steviol glycosides on blood glucose and on blood

  15. Reverse Transcription-PCR

    NSDL National Science Digital Library

    American Society For Microbiology

    2003-05-12

    This Flash animation shows how the method of reverse transcription-PCR is performed and some sample data are produced. It uses sound and mouse-over identification to help students learn more and retain the information.

  16. Reversible shape memory

    NASA Astrophysics Data System (ADS)

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

    2012-02-01

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

  17. 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.

  18. On time reversal mirrors

    Microsoft Academic Search

    Albert C. Fannjiang

    2009-01-01

    The concept of time reversal (TR) of scalar wave is reexamined from basic\\u000aprinciples. Five different time reversal mirrors (TRM) are introduced and their\\u000arelations are analyzed. For the boundary behavior, it is shown that for\\u000aparaxial wave only the monopole TR scheme satisfies the exact boundary\\u000acondition while for spherical wave only one of the mixed mode TR scheme,

  19. Thermal decomposition study of menthyl-glycoside by TGA\\/SDTA, DSC and simultaneous Py-GC–MS analysis

    Microsoft Academic Search

    Wan-cui Xie; Jian Tang; Xiao-hong Gu; Chang-rong Luo; Guang-yu Wang

    2007-01-01

    To develop thermal stable flavor, a glycosidic bond flavor precursor of menthyl-?-d-glucopyranoside (MGLY) was synthesized by the modified Koenigs–Knorr reaction. The thermal decomposition process and pyrolysis products of the glycoside were investigated by thermo-gravimetric and simultaneously differential thermal analysis (TGA\\/SDTA), differential scanning calorimeter (DSC) and on-line pyrolysis-gas chromatography–mass spectroscopy (Py-GC–MS). TGA\\/SDTA gave the TG–DTG and DTA curves simultaneously, the TG–DTG

  20. Flavonoids of the epigeal part of Rhodiola rosea . II. Structures of new glycosides of herbacetin and of gossypetin

    Microsoft Academic Search

    G. G. Zapesochnaya; V. A. Kurkin; A. N. Shchavlinskii

    1985-01-01

    The structure of four new flavonol glycosides isolated from the epigeal part ofRhodiola rosea have been established: 7-O-?-L-rhamnopyranosylgossypetin (rhodiolgin), 8-O-?-D-glucopyranosyl-7-O-?-L-rhamnopyranosylgossypetin\\u000a (rhodiolgidin), 8-O-?-D-glucopyranosol-7-O-?-L-rhamnopyranosylherbacetin (rhodionidin), and 3-O-?-D-glucopyranosyl-8-O-?-D-xylopyranosylherbacetin\\u000a (rhodalidin). The properties of the previously undescribed incomplete methyl ethers of herbacetin and gossypetin obtained\\u000a during the structural analysis of the glycosides have been studied. It has been found that diazomethane methylates the 5-OH\\u000a groups

  1. [Effect of glycosides of betulafolientriol and its 3-epimer on the growth of tumor cells in vitro].

    PubMed

    Shentsova, E B; Anisimov, M M; Loenko, Iu N; Atopkina, L N; Samoshina, N F; Uvarova, N I

    1989-11-01

    The effect of triterpene glycosides synthesized on the basis of betulafolientriol, ginsenoside Rb1 from gingseng, betulafolientriol and its 3-epimer on the growth of the Ehrlich tumor cell cultures was studied. It was shown that, in relation to the quantitative composition and sites of carbohydrate residue linkage to aglycone as well as configuration of the alpha- or beta-hydroxyl group at C-3, the activity of the triterpenoids of the dammaranic series changed within wide ranges. 3- and 12-0-beta-D-glycosides of 3-epibetulafolientriol proved to be the most active. PMID:2633697

  2. Highly Stereoselective Synthesis of Lamivudine (3TC) and Emtricitabine (FTC) by a Novel N-Glycosidation Procedure.

    PubMed

    Caso, Maria Federica; D'Alonzo, Daniele; D'Errico, Stefano; Palumbo, Giovanni; Guaragna, Annalisa

    2015-06-01

    The combined use of silanes (Et3SiH or PMHS) and I2 as novel N-glycosidation reagents for the synthesis of bioactive oxathiolane nucleosides 3TC and FTC is reported. Both systems (working as anhydrous HI sources) were devised to act as substrate activators and N-glycosidation promoters. Excellent results in terms of chemical efficiency and stereoselectivity of the reactions were obtained; surprisingly, the nature of the protective group at the N4 position of (fluoro)cytosine additionally influenced the stereochemical reaction outcome. PMID:25965958

  3. A new iridoid glycoside and potential MRB inhibitory activity of isolated compounds from the rhizomes of Cyperus rotundus L.

    PubMed

    Zhou, Zhongliu; Yin, Wenqing; Zhang, Hualin; Feng, Zongcai; Xia, Jingmin

    2013-01-01

    A new iridoid glycoside, rotunduside (1), along with four known iridoid glycosides, 10-O-p-hydroxybenzoyltheviridoside (2), 10-O-vanilloyltheviridoside (3), 6?-O-(trans-p-coumaroyl)-procumbide (4) and loganic acid (5), was isolated from the rhizomes of Cyperus rotundus L. Their chemical structures were elucidated on the basis of UV, IR, MS and NMR spectroscopic analyses. In addition, the macrophages respiratory burst (MRB) inhibitory activity of the isolated compounds was reported. Compound 2 exhibited considerable MRB inhibitory activity in the test with IC50 value of ~37 ?M. PMID:23356789

  4. Discovery of selective small-molecule activators of a bacterial glycoside hydrolase.

    PubMed

    Darby, John F; Landström, Jens; Roth, Christian; He, Yuan; Davies, Gideon J; Hubbard, Roderick E

    2014-12-01

    Fragment-based approaches are used routinely to discover enzyme inhibitors as cellular tools and potential therapeutic agents. There have been few reports, however, of the discovery of small-molecule enzyme activators. Herein, we describe the discovery and characterization of small-molecule activators of a glycoside hydrolase (a bacterial O-GlcNAc hydrolase). A ligand-observed NMR screen of a library of commercially available fragments identified an enzyme activator which yielded an approximate 90?% increase in kcat /KM ?values (kcat =catalytic rate constant; KM =Michaelis constant). This compound binds to the enzyme in close proximity to the catalytic center. Evolution of the initial hits led to improved compounds that behave as nonessential activators effecting both KM ?and Vmax ?values (Vmax =maximum rate of reaction). The compounds appear to stabilize an active "closed" form of the enzyme. Such activators could offer an orthogonal alternative to enzyme inhibitors for perturbation of enzyme activity in?vivo, and could also be used for glycoside hydrolase activation in many industrial processes. PMID:25291993

  5. Influence of 4'-O-Glycoside Constitution and Configuration on Ribosomal Selectivity of Paromomycin.

    PubMed

    Matsushita, Takahiko; Chen, Weiwei; Juskeviciene, Reda; Teo, Youjin; Shcherbakov, Dimitri; Vasella, Andrea; Böttger, Erik C; Crich, David

    2015-06-24

    A series of 20 4'-O-glycosides of the aminoglycoside antibiotic paromomycin were synthesized and evaluated for their ability to inhibit protein synthesis by bacterial, mitochondrial and cytosolic ribosomes. Target selectivity, i.e., inhibition of the bacterial ribosome over eukaryotic mitochondrial and cytosolic ribosomes, which is predictive of antibacterial activity with reduced ototoxicity and systemic toxicity, was greater for the equatorial than for the axial pyranosides, and greater for the d-pentopyranosides than for the l-pentopyranosides and d-hexopyranosides. In particular, 4'-O-?-d-xylopyranosyl paromomycin shows antibacterioribosomal activity comparable to that of paromomycin, but is significantly more selective showing considerably reduced affinity for the cytosolic ribosome and for the A1555G mutant mitochondrial ribosome associated with hypersusceptibility to drug-induced ototoxicity. Compound antibacterioribosomal activity correlates with antibacterial activity, and the ribosomally more active compounds show activity against Escherichia coli, Klebsiella pneumonia, Enterobacter cloacae, Acinetobacter baumannii, and methicillin-resistant Staphylococcus aureus (MRSA). The paromomycin glycosides retain activity against clinical strains of MRSA that are resistant to paromomycin, which is demonstrated to be a consequence of 4'-O-glycosylation blocking the action of 4'-aminoglycoside nucleotidyl transferases by the use of recombinant E. coli carrying the specific resistance determinant. PMID:26024064

  6. Production of a Novel Quercetin Glycoside through Metabolic Engineering of Escherichia coli

    PubMed Central

    Yoon, Jeong-A; Kim, Bong-Gyu; Lee, Woo Ju; Lim, Yoongho; Chong, Youhoon

    2012-01-01

    Most flavonoids exist as sugar conjugates. Naturally occurring flavonoid sugar conjugates include glucose, galactose, glucuronide, rhamnose, xylose, and arabinose. These flavonoid glycosides have diverse physiological activities, depending on the type of sugar attached. To synthesize an unnatural flavonoid glycoside, Actinobacillus actinomycetemcomitans gene tll (encoding dTDP-6-deoxy-l-lyxo-4-hexulose reductase, which converts the endogenous nucleotide sugar dTDP-4-dehydro-6-deoxy-l-mannose to dTDP-6-deoxytalose) was introduced into Escherichia coli. In addition, nucleotide-sugar dependent glycosyltransferases (UGTs) were screened to find a UGT that could use dTDP-6-deoxytalose. Supplementation of this engineered strain of E. coli with quercetin resulted in the production of quercetin-3-O-(6-deoxytalose). To increase the production of quercetin 3-O-(6-deoxytalose) by increasing the supplement of dTDP-6-deoxytalose in E. coli, we engineered nucleotide biosynthetic genes of E. coli, such as galU (UTP-glucose 1-phosphate uridyltransferase), rffA (dTDP-4-oxo-6-deoxy-d-glucose transaminase), and/or rfbD (dTDP-4-dehydrorahmnose reductase). The engineered E. coli strain produced approximately 98 mg of quercetin 3-O-(6-deoxytalose)/liter, which is 7-fold more than that produced by the wild-type strain, and the by-products, quercetin 3-O-glucose and quercetin 3-O-rhamnose, were also significantly reduced. PMID:22492444

  7. Metabolic engineering of the flavone-C-glycoside pathway using polyprotein technology.

    PubMed

    Brazier-Hicks, Melissa; Edwards, Robert

    2013-03-01

    C-Glycosylated flavonoids are biologically active plant natural products linked to dietary health benefits. We have used polyprotein expression technology to reconstruct part of the respective biosynthetic pathway in tobacco and yeast, such that dihydrochalcone and flavanone precursors are directly converted to C-glycosides. The polyprotein system developed facilitated the simple and efficient co-expression of pathway enzymes requiring different sub-cellular localization in both plants and yeast. The pathway to flavone-C-glucosides comprised a flavanone 2-hydroxylase (F2H), co-expressed with a C-glucosyltransferase (CGT). While pathway engineering in tobacco resulted in only minor C-glycoside formation, when fed with the flavanone naringenin, yeast transformed with the F2H-CGT polyprotein construct produced high concentrations of 2-hydroxynaringenin-C-glucoside in the medium. These fermentation products could then be readily chemically converted to the respective flavone-C-glucosides. The efficiency of the biosynthesis was optimal when both the F2H and CGT were obtained from the same species (rice). These results confirm the coupled roles of the F2H and CGT in producing C-glucosides in vivo, with the use of the polyprotein expression system in yeast offering a useful system to optimize the synthesis of these natural products in quantities suitable for dietary studies. PMID:23246521

  8. Influence of drying method on steviol glycosides and antioxidants in Stevia rebaudiana leaves.

    PubMed

    Periche, Angela; Castelló, María Luisa; Heredia, Ana; Escriche, Isabel

    2015-04-01

    The application of different drying conditions (hot air drying at 100 °C and 180 °C, freeze drying and shade drying) on steviol glycosides (stevioside, dulcoside A, rebaudioside A and rebaudioside C) and antioxidants in Stevia leaves was evaluated. Stevioside, the major glycoside found in fresh leaves (81.2mg/g), suffered an important reduction in all cases, although shade drying was the least aggressive treatment. Considering the antioxidant parameters (total phenols, flavonoids and total antioxidants), the most suitable drying method was hot air at 180 °C, since it substantially increased all of them (76.8 mg gallic acid, 45.1mg catechin and 126 mg Trolox, all equivalent/g Stevia, respectively), with respect to those present in fresh leaves (44.4, 2.5 and 52.9 mg equivalent/g). Therefore, the ideal method for drying Stevia leaves depends on their final use (sweetener or antioxidant), although, hot air at 180 °C is the most recommendable if only one treatment has to be chosen. PMID:25442516

  9. New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit.

    PubMed

    Miyake, Yoshiaki; Minato, Kenichiro; Fukumoto, Syuichi; Yamamoto, Kanefumi; Oya-Ito, Tomoko; Kawakishi, Syunro; Osawa, Toshihiko

    2003-07-01

    Potent antioxidative hydroxyflavanones were produced with Aspergillus saitoi from hesperidin or naringin, which are flavanone glycosides in citrus fruit with weak antioxidative activity. The hydroxyflavanone produced from hesperidin was identified as 8-hydroxyhesperetin (8-HHE), a novel substance, and those from naringin were identified as carthamidin (6-hydroxynaringenin) and isocarthamidin (8-hydroxynaringenin) by FAB-MS, 1H-NMR and 13C-NMR analyses. The antioxidative activity of these hydroxyflavanones was examined by using the free radical-scavenging system of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the methyl linoleate oxidation system. The hydroxyflavanones (8-HHE, carthamidin, and isocarthamidin) exhibited stronger activity than the flavanone glycosides (hesperidin or naringin) and their aglycones (hesperetin or naringenin). The activity of 8-HHE and isocarthamidin was comparable to that of alpha-tocopherol, and that of carthamidin was weaker than that of isocarthamidin. The hydroxyflavanones, which were hydroxylated on A ring of flavanone by Aspergillus saitoi, were obtained as potent antioxidants. PMID:12913285

  10. HPLC-MSn identification and quantification of flavonol glycosides in 28 wild and cultivated berry species.

    PubMed

    Mikulic-Petkovsek, Maja; Slatnar, Ana; Stampar, Franci; Veberic, Robert

    2012-12-15

    Berries and red fruits are rich dietary sources of polyphenols with reported health benefits. More than 50 different flavonols (glycosides of quercetin, myricetin, kaempferol, isorhamnetin, syringetin and laricitrin) have been detected and quantified with HPLC-MS(n) in fruits of blueberry, bilberry, cranberry, lingonberry, eastern shadbush, Japanese wineberry, black mulberry, chokeberry, red, black and white currants, jostaberry, red and white gooseberry, hardy kiwifruit, goji berry, rowan, dog rose, Chinese and midland hawthorn, wild and cultivated species of blackberry, raspberry, strawberry and elderberry. The phenolic constituents and contents varied considerably among the analyzed berry species. Elderberry contained the highest amount of total flavonols (450-568 mgkg(-1) FW), followed by berry species, containing more than 200 mgkg(-1) FW of total: chokeberry (267mgkg(-1)), eastern shadbush (261 mgkg(-1)), wild grown blackberry (260 mgkg(-1)), rowanberry (232 mgkg(-1)), american cranberry (213 mgkg(-1)) and blackcurrants (204 mgkg(-1)). Strawberry (10.5 mgkg(-1)) and white currants (4.5 mgkg(-1)) contained the lowest amount of total flavonols. Quercetins represent the highest percentage (46-100%) among flavonols in most analyzed berries. In wild strawberry and gooseberry the prevailing flavonols belong to the group of isorhamnetins (50-62%) and kaempferols, which represent the major part of flavonols in currants (49-66%). Myricetin glycosides could only be detected in chokeberry, rowanberry and species from the Grossulariaceae, and Adoxaceae family and Vaccinium genus. Wild strawberry and blackberry contained from 3- to 5-fold higher total flavonols than the cultivated one. PMID:22980782

  11. Ability of human oral microbiota to produce wine odorant aglycones from odourless grape glycosidic aroma precursors.

    PubMed

    Muńoz-González, Carolina; Cueva, Carolina; Ángeles Pozo-Bayón, M; Victoria Moreno-Arribas, M

    2015-11-15

    Grape aroma precursors are odourless glycosides that represent a natural reservoir of potential active odorant molecules in wines. Since the first step of wine consumption starts in the oral cavity, the processing of these compounds in the mouth could be an important factor in influencing aroma perception. Therefore, the objective of this work has been to evaluate the ability of human oral microbiota to produce wine odorant aglycones from odourless grape glycosidic aroma precursors previously isolated from white grapes. To do so, two methodological approaches involving the use of typical oral bacteria or the whole oral microbiota isolated from human saliva were followed. Odorant aglycones released in the culture mediums were isolated and analysed by HS-SPME-GC/MS. Results showed the ability of oral bacteria to hydrolyse grape aroma precursors, releasing different types of odorant molecules (terpenes, benzenic compounds and lipid derivatives). The hydrolytic activity seemed to be bacteria-dependent and was subject to large inter-individual variability. PMID:25977005

  12. ?-Glucosidase inhibitory effect and simultaneous quantification of three major flavonoid glycosides in Microctis folium.

    PubMed

    Chen, Yan-Gan; Li, Ping; Li, Peng; Yan, Ru; Zhang, Xiao-Qi; Wang, Ying; Zhang, Xian-Tao; Ye, Wen-Cai; Zhang, Qing-Wen

    2013-01-01

    Microctis Folium, the leaves of Microcos paniculata L., is a commonly used herbal tea material. The methanol extract of Microctis Folium and its principle compounds vitexin (1), isovitexin (2) and isorhamnetin 3-O-?-D-rutinoside (3) were investigated for their ?-glucosidase inhibitory effects. The extract showed strong ?-glucosidase inhibitory effect (IC?? = 61.30 ?g/mL) and the three flavonoid glycosides 1-3 exerted satisfactory ?-glucosidase inhibitory effects, with IC?? values of 244.0 ?M, 266.2 ?M and 275.4 ?M, respectively. A simple and reliable HPLC-DAD method was developed for the quantification of the three flavonoid glycosides in Microctis Folium and applied successfully to determine contents of these components in samples collected from different locations. This study suggested that Microctis Folium may be a promising candidate for development of herbal antidiabetes drugs, and vitexin, isovitexin and isorhamnetin 3-O-?-D-rutinoside can be the biomarkers and chemical markers for this plant substance. PMID:23612474

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

    PubMed

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

    2014-12-01

    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

  14. Crystal structure of glycoside hydrolase family 127 ?-l-arabinofuranosidase from Bifidobacterium longum.

    PubMed

    Ito, Tasuku; Saikawa, Kyo; Kim, Seonah; Fujita, Kiyotaka; Ishiwata, Akihiro; Kaeothip, Sophon; Arakawa, Takatoshi; Wakagi, Takayoshi; Beckham, Gregg T; Ito, Yukishige; Fushinobu, Shinya

    2014-04-25

    Enzymes acting on ?-linked arabinofuranosides have been unknown until recently, in spite of wide distribution of ?-l-arabinofuranosyl oligosaccharides in plant cells. Recently, a ?-l-arabinofuranosidase from the glycoside hydrolase family 127 (HypBA1) was discovered in the newly characterized degradation system of hydroxyproline-linked ?-l-arabinooligosaccharides in the bacterium Bifidobacterium longum. Here, we report the crystal structure of HypBA1 in the ligand-free and ?-l-arabinofuranose complex forms. The structure of HypBA1 consists of a catalytic barrel domain and two additional ?-sandwich domains, with one ?-sandwich domain involved in the formation of a dimer. Interestingly, there is an unprecedented metal-binding motif with Zn(2+) coordinated by glutamate and three cysteines in the active site. The glutamate residue is located far from the anomeric carbon of the ?-l-arabinofuranose ligand, but one cysteine residue is appropriately located for nucleophilic attack for glycosidic bond cleavage. The residues around the active site are highly conserved among GH127 members. Based on biochemical experiments and quantum mechanical calculations, a possible reaction mechanism involving cysteine as the nucleophile is proposed. PMID:24680821

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

    PubMed

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

    2013-01-01

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

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

    PubMed Central

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

    2014-01-01

    ?-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

  17. Effects of salt stress on the growth, physiological responses, and glycoside contents of Stevia rebaudiana Bertoni.

    PubMed

    Zeng, Jianwei; Chen, Aimeng; Li, Dandan; Yi, Bin; Wu, Wei

    2013-06-19

    This study examined the effects of three different NaCl concentrations (60, 90, and 120 mM) on the growth, physiological responses, and steviol glycoside composition of Stevia rebaudiana Bertoni for 4 weeks. The results showed that the total dry weight decreased by 40% at 120 mM NaCl but remained the same at 60 and 90 mM NaCl. As salt concentration increased, chlorophyll contents decreased markedly by 10-70%, whereas the increments of the antioxidant enzyme activities were 1.0-1.6, 1.2-1.3, and 2.0-4.0 times, respectively, for superoxide dismutase, peroxidase, and catalase. The proline contents in salt-treated plants were 17-42 times higher than that in control. Moreover, leaf possessed significantly higher K? content and K?/Na? ratio than stem and root for all salt treatments. In addition, 90-120 mM NaCl treatment notably decreased the content of rebaudioside A (RA) and stevioside (ST) by 16.2-38.2%, whereas the increment of the ratio of RA/ST of salt-treated plants was 1.1-1.4 times. These results indicate that S. rebaudiana is moderately tolerant to salt stress. Hypohaline soil can be utilized in the plantation of S. rebaudiana and may be profitable for optimizing the steviol glycoside composition. PMID:23711229

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

    PubMed

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

    2015-01-01

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

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

    SciTech Connect

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

    2009-11-15

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

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

    SciTech Connect

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

    2011-05-11

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

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

    PubMed

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

    2014-01-15

    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

  2. --Guest Editorial --Software Reverse Engineering

    E-print Network

    van Deursen, Arie

    -- Guest Editorial -- Software Reverse Engineering Arie van Deursen a,b Liz Burd c aCWI, P.O. Box, UK Introduction Reverse engineering aims at obtaining high level representations of programs. Reverse just given, source code, architectural views, or use cases, respectively). Reverse engineering methods

  3. The logic of time reversal

    Microsoft Academic Search

    E. J. Post

    1979-01-01

    Active time reversal in the sense of ``object reversal'' and passive time reversal in the sense of a frame reversal of time are discussed separately and then together so as to bring out their dual nature. An understanding of that duality makes it unavoidable to contrast symmetry properties of matter with symmetry properties to be assigned to antimatter. Only frame

  4. The logic of time reversal

    Microsoft Academic Search

    E. J. Post

    1979-01-01

    Active time reversal in the sense of object reversal and passive time reversal in the sense of a frame reversal of time are discussed separately and then together so as to bring out their dual nature. An understanding of that duality makes it unavoidable to contrast symmetry properties of matter with symmetry properties to be assigned to antimatter. Only frame

  5. Determination of flavonol glycosides in green tea, oolong tea and black tea by UHPLC compared to HPLC.

    PubMed

    Jiang, Heyuan; Engelhardt, Ulrich H; Thräne, Claudia; Maiwald, Beate; Stark, Janina

    2015-09-15

    An UHPLC method for the determination of flavonol glycosides (FOG) from green and oolong tea vs. black tea has been developed for the first time. Sample clean-up method by means of polyamide column chromatography was optimized with multiple-step elution. Using UHPLC and HPLC with gradient elution and photodiode array detection, eighteen FOG compounds were determined with the aid of electrospray tandem mass spectrometry. These FOG compounds were qualified on both UHPLC and HPLC, and this UHPLC method successfully separated rutin (quercetin-3-O-rutinoside) and K-grg (kaempferol-3-O-glucorhamnoglucoside) while conventional HPLC method did not. The total amounts of FOG compounds in the tea samples were 2.32-5.67g/kg dry weight (calculated as aglycones), and there is no significant difference for the total FOG content among green tea, oolong tea and black tea. However, kaempferol glycosides are more abundant in green teas, while oolong tea has more quercetin and myricetin glycosides. In black tea quercetin glycosides were most abundant. PMID:25863606

  6. Induction of Phenolic Glycosides by Quaking Aspen ( Populus tremuloides) Leaves in Relation to Extrafloral Nectaries and Epidermal Leaf Mining

    Microsoft Academic Search

    Brian Young; Diane Wagner; Patricia Doak; Thomas Clausen

    2010-01-01

    We studied the effect of epidermal leaf mining on the leaf chemistry of quaking aspen, Populus tremuloides, during an outbreak of the aspen leaf miner, Phyllocnistis populiella, in the boreal forest of interior Alaska. Phyllocnistis populiella feeds on the epidermal cells of P. tremuloides leaves. Eleven days after the onset of leaf mining, concentrations of the phenolic glycosides tremulacin and

  7. Tectoridin, an isoflavone glycoside from the flower of Pueraria lobata, prevents acute ethanol-induced liver steatosis in mice

    Microsoft Academic Search

    Yu Xiong; Yuqing Yang; Jin Yang; Hongyan Chai; Ying Li; Jing Yang; Ziming Jia; Zhengrong Wang

    2010-01-01

    In traditional Chinese medicine, the flower of Pueraria lobata (Puerariae Flos) has been used in therapy to counteract the problems associated with alcohol drinking and liver injury. In this study, we investigated the hepatoprotective effects and its mechanisms of tectoridin, an isoflavone glycoside from the flower of P. lobata (Willd.) Ohwi. Ethanol (5g\\/kg) was given orally every 12h for a

  8. Plant-Glycoside Modulation of Cell Surface Related to Control of Differentiation in Cultured B16 Melanoma Cells1

    Microsoft Academic Search

    Takahide Ota; Kohzaburo Fujikawa-yamamoto; Zhi-ping Zong; Masakazu Yamazaki; Shizuo Odashirna; Isao Kitagawa; Hiroko Abe; Shigeru Arichi

    We have shown that the ginsenosides Kit, and Rh2, which are plant glycosides with a dammarane skeleton resembling a steroid skeleton as an aglycone, control the phenotypic expression of mouse B16 melanoma cells in different ways. The effects of Rh, and Rh2 on the cell surface were studied to clarify the relationship between the control of phenotypic expression and modification

  9. Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum growing in Tunisia.

    PubMed

    Hammami, S; Ben Jannet, H; Bergaoui, A; Ciavatta, L; Cimino, G; Mighri, Z

    2004-01-01

    A flavanone and a flavanone glycoside, together with vomifoliol, have been isolated for the first time from the aerial parts of the plant Echiochilon fruticosum and identified. Their structures were established on the basis of spectroscopic measurements, mainly 2D NMR using COSY, HMQC and HMBC experiments. PMID:18007460

  10. Isolation and Structure Elucidation of a Flavanone, a Flavanone Glycoside and Vomifoliol from Echiochilon Fruticosum Growing in Tunisia

    Microsoft Academic Search

    S. Hammami; H. Ben Jannet; A. Bergaoui; L. Ciavatta; G. Cimino; Z. Mighri

    2004-01-01

    A flavanone and a flavanone glycoside, together with vomifoliol, have been isolated for the first time from the aerial parts of the plant Echiochilon fruticosum and identified. Their structures were established on the basis of spectroscopic measurements, mainly 2D NMR using COSY, HMQC and HMBC experiments.

  11. 2724 J. Org. Chem. 1994,59, 2724-2728 Boronic Acids Mediate Glycoside Transport through a Liquid

    E-print Network

    Smith, Bradley D.

    was achieved by including boric acid in the receiving phase and lipophilic boronic acid in the organic layer2724 J. Org. Chem. 1994,59, 2724-2728 Boronic Acids Mediate Glycoside Transport through a Liquid of Notre Dame, Notre Dame, Indiana 46556 Received December 29, 1993 The ability of phenylboronic acid and 3

  12. Stabilization of cucurbitacin E-glycoside, a feeding stimulant for diabroticite beetles, extracted from bitter Hawkesbury watermelon

    Microsoft Academic Search

    Phyllis A. W. Martin; Michael Blackburn; Robert F. W. Schroder; Koharto Matsuo; Betty W. Li

    Cucurbitacins are feeding stimulants for diabroticite beetles, including corn rootworms and cucumber beetles, which can be added to a bait containing an insecticide thereby reducing the levels of other insecticide treatments needed to control these pests. One of them, cucurbitacin E- glycoside, is water soluble and easily processed from mutant bitter Hawkesbury watermelons (BHW) that express elevated levels of cucurbitacin.

  13. Re-evaluating the role of ascorbic acid and phenolic glycosides in ozone scavenging in the leaf apoplast of

    E-print Network

    Jones, Alan M.

    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

  14. 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...

  15. INFLUENCE OF GLYCOSIDIC LINKAGES AND MOLECULAR WEIGHT ON THE FERMENTATION OF MALTOSE-BASED OLIGOSACCHARIDES BY GUT BACTERIA

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A structure-function study was carried out to increase knowledge of how glycosidic linkages and molecular weight of carbohydrates contribute towards the selectivity of fermentation by gut bacteria. Oligosaccharides with maltose as the common carbohydrate source were used. Potentially prebiotic alt...

  16. Three unusual 22-beta-O-23-hydroxy-(5 alpha)-spirostanol glycosides from the fruits of Solanum torvum.

    PubMed

    Iida, Yoshihiko; Yanai, Yoshihiro; Ono, Masateru; Ikeda, Tsuyoshi; Nohara, Toshihiro

    2005-09-01

    Three novel 22-beta-O-spirostanol oligoglycosides, torvosides J (1), K (2) and L (3) have been isolated from the fruits of Solanum torvum SWARTZ and their chemical structures have been characterized based on the spectroscopic means. They are worth of note as rare 22-beta-O-spirostanol glycosides. PMID:16141580

  17. Differential toxicity of a phenolic glycoside from quaking aspen to Papilio glaucus butterfly subspecies, hybrids and backcrosses

    Microsoft Academic Search

    J. Mark Scriber; Richard L. Lindroth; James Nitao

    1989-01-01

    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

  18. Chloroplast ultrastructure, photosynthetic apparatus activities and production of steviol glycosides in Stevia rebaudiana in vivo and in vitro

    Microsoft Academic Search

    V. G. Ladygin; N. I. Bondarev; G. A. Semenova; A. A. Smolov; O. V. Reshetnyak; A. M. Nosov

    2008-01-01

    The accumulation of steviol glycosides (SGs) in cells of Stevia rebaudiana Bertoni both in vivo and in vitro was related to the extent of the development of the membrane system of chloroplasts and the content of photosynthetic pigments.\\u000a Chloroplasts of the in vitro plants, unlike those of the intact plants, had poorly developed membrane system. The callus cells grown in

  19. Determination of six steviol glycosides of Stevia rebaudiana (Bertoni) from different geographical origin by LC-ESI-MS/MS.

    PubMed

    Montoro, Paola; Molfetta, Ilaria; Maldini, Mariateresa; Ceccarini, Lucia; Piacente, Sonia; Pizza, Cosimo; Macchia, Mario

    2013-11-15

    Liquid chromatography electro-spray tandem mass spectrometry (LC-ESI/MS/MS) was applied to the determination of sweet glycosides (steviol glycosides), and toxic aglycon steviol in 24 samples of Stevia rebaudiana (Bertoni) aerial parts, which had been experimentally cultivated in Italy, although derived from seeds of different geographical origin. On the basis of the specific fragmentation of these compounds, an LC-MS/MS method was developed with the aim of quantifying analytes in plant material. Although toxic steviol was not detectable in all the samples, the samples with the highest levels of steviol glycosides were identified. Analysis of the different samples revealed that they were good quality samples, quality being directly linked to the presence of sweet glycosides in the plants cultivated in Italy, although there were differences in the content of these compounds according to the origin of the seeds, and in particular, a major concentration of compounds with major sweetness activity and minor toxicity was found in the population coming from Brazil (for example: sample 10, stevioside content 15.74±2.0% p/p and rebaudioside A content 3.09±0.39% p/p of dried plant). Finally, based on this metabolomic targeted approach, the results obtained for the samples were treated by Principal Component Analysis, identifying specific genotypic differences based on the geographic origin of the seeds. PMID:23790843

  20. 49 CFR 230.89 - Reverse gear.

    Code of Federal Regulations, 2010 CFR

    2010-10-01

    ... 2010-10-01 2010-10-01 false Reverse gear. 230.89 Section 230.89 Transportation...Throttles and Reversing Gear § 230.89 Reverse gear. (a) General provisions. Reverse gear, reverse levers, and quadrants...

  1. 49 CFR 230.89 - Reverse gear.

    Code of Federal Regulations, 2011 CFR

    2011-10-01

    ... 2011-10-01 2011-10-01 false Reverse gear. 230.89 Section 230.89 Transportation...Throttles and Reversing Gear § 230.89 Reverse gear. (a) General provisions. Reverse gear, reverse levers, and quadrants...

  2. Unlike Quercetin Glycosides, Cyanidin Glycoside in Red Leaf Lettuce Responds More Sensitively to Increasing Low Radiation Intensity before than after Head Formation Has Started

    PubMed Central

    2014-01-01

    This study investigated the effect of low-level photosynthetic photon flux density (PPFD; 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

  3. Unlike quercetin glycosides, cyanidin glycoside in red leaf lettuce responds more sensitively to increasing low radiation intensity before than after head formation has started.

    PubMed

    Becker, Christine; Klaering, Hans-Peter; Schreiner, Monika; Kroh, Lothar W; Krumbein, Angelika

    2014-07-23

    This study investigated the effect of low-level photosynthetic photon flux density (PPFD; 43-230 ?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

  4. Glucose reversion reaction kinetics.

    PubMed

    Pilath, Heidi M; Nimlos, Mark R; Mittal, Ashutosh; Himmel, Michael E; Johnson, David K

    2010-05-26

    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

  5. Enzymatic synthesis of L-DOPA alpha-glycosides by reaction with sucrose catalyzed by four different glucansucrases from four strains of Leuconostoc mesenteroides.

    PubMed

    Yoon, Seung-Heon; Fulton, D Bruce; Robyt, John F

    2010-08-16

    L-DOPA alpha-glycosides were synthesized by reaction of L-DOPA with sucrose, catalyzed by four different glucansucrases from Leuconostoc mesenteroides B-512FMC, B-742CB, B-1299A, and B-1355C. The glucansucrases catalyzed the transfer of d-glucose from sucrose to the phenolic hydroxyl position-3 and -4 of L-DOPA. The glycosides were fractionated and purified by Bio-Gel P-2 column chromatography, and the structures were determined by (1)H NMR spectroscopy. The major glycoside was 4-O-alpha-d-glucopyranosyl L-DOPA, and the minor glycoside was 3-O-alpha-D-glucopyranosyl L-DOPA. The two glycosides were formed by all four of the glucansucrases. The ratio of the 4-O-alpha-glycoside to the 3-O-alpha-glycoside produced by the B-512FMC dextransucrase was higher than that for the other three glucansucrases. The glycosylation of L-DOPA significantly reduced the oxidation of the phenolic hydroxyl groups, which prevents their methylation, potentially increasing the use of L-DOPA in the treatment of Parkinson's disease. The use of one enzyme, glucansucrase, and sucrose as the D-glucosyl donor makes the synthesis considerably simpler and cheaper than the formerly published procedure using cyclomaltodextrin and cyclomaltodextrin glucanyltransferase, followed by glucoamylase, and beta-amylase hydrolysis. PMID:20579635

  6. REVERSE ENGINEERING OF MOLECULAR

    E-print Network

    Sontag, Eduardo

    requires insight into the structure and dynamics of networks that are made up of thousands of interacting and interacting networks of genes, proteins, and other molecu- lar species through biochemical reactions40 REVERSE ENGINEERING OF MOLECULAR NETWORKS FROM A COMMON COMBINATORIAL APPROACH Bhaskar Das

  7. Cells in Reverse

    NSDL National Science Digital Library

    American Association for the Advancement of Science (; )

    2006-05-29

    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.

  8. Nanocomputers and Reversible Logic

    Microsoft Academic Search

    J. Storrs Hall

    1994-01-01

    An overview of nanocomputers is given, including a discussion of reversible computing techniques and an explanation of why they are necessary. 1 Nanocomputers I usually begin this talk by trying to justify why we need nanocomputers in the first place. As Caxton Foster once said of associative memory, nanocomputers would seem to hold out the promise of sugar tomorrow to

  9. Reversible variable length codes

    Microsoft Academic Search

    Y. Takishima; M. Wada; H. Murakami

    1995-01-01

    Proposes some reversible variable length codes (RVLCs) which can be decoded instantaneously both in the forward and backward directions and have high transmission efficiency. These codes can be used, for example, in the backward reconstruction of video signals from the data last received when some signal is lost midway in the transmission. Schemes for a symmetrical RVLC requiring only a

  10. Time-reversal acoustics

    Microsoft Academic Search

    Mathias Fink

    2008-01-01

    Time-reversal mirrors (TRMs) refocus an incident acoustic field to the position of the original source regardless of the complexity of the propagation medium. TRM's have now been implemented in a variety of physical scenarios from MHz ultrasonics with order centimeter aperture size to hundreds\\/thousands of Hz in ocean acoustics with order hundred meter aperture size. Common to this broad range

  11. Reverse cycle heat pump

    Microsoft Academic Search

    Harnish

    1977-01-01

    A reverse cycle heat pump is provided with a heat exchanger which provides refrigerant subcooling with no thermodynamic losses. The heat exchanger is arranged such that it is operative only during the heating cycle to permit optimum charging of the system and allow operation during the cooling cycle with no excess refrigerant in the system accumulator. The heat exchanger is

  12. Reversible Thermoelectric Nanomaterials

    Microsoft Academic Search

    T. E. Humphrey; H. Linke

    2005-01-01

    Irreversible effects in thermoelectric materials limit their efficiency and economy for applications in power generation and refrigeration. While electron transport is unavoidably irreversible in bulk materials, here we derive conditions under which reversible diffusive electron transport can be achieved in nanostructured thermoelectric materials. We provide a fundamental thermodynamic explanation for why the optimum density of states in a thermoelectric material

  13. On reverse hypercontractivity

    E-print Network

    Mossel, Elchanan; Sen, Arnab

    2011-01-01

    We study the notion of reverse hypercontractivity. We show that reverse hypercontractive inequalities are implied by standard hypercontractive inequalities as well as by the modified log-Sobolev inequality. Our proof is based on a new comparison lemma for Dirichlet forms and an extension of the Strook-Varapolos inequality. A consequence of our analysis is that {\\em all} simple operators $L=Id-\\E$ as well as their tensors satisfy uniform reverse hypercontractive inequalities. That is, for all $qreverse hypercontractive inequalities established here imply new mixing and isoperimetric results for short random walks in product spaces, for certain card-shufflings, for Glauber dynamics in high-temperat...

  14. Expression pattern of glycoside hydrolase genes in Lutzomyia longipalpis reveals key enzymes involved in larval digestion

    PubMed Central

    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

    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

  15. Lignan Glycosides from the Twigs of Chaenomeles sinensis and Their Biological Activities.

    PubMed

    Kim, Chung Sub; Subedi, Lalita; Kim, Sun Yeou; Choi, Sang Un; Kim, Ki Hyun; Lee, Kang Ro

    2015-05-22

    Phytochemical investigation of the twigs of Chaenomeles sinensis led to the isolation and identification of six new lignan glycosides, chaenomiside A-F (1-6), along with five known ones (7-11). Their chemical structures were determined by spectroscopic methods, including NMR, MS, ECD, and GC/MS analyses. All the isolated compounds (1-11) were tested for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide-activated murine microglial cells and the secretion of nerve growth factor (NGF) in a C6 rat glioma cell line. Compound 6 significantly reduced NO levels in the murine microglia BV2 cells with an IC50 value of 21.3 ?M, and compounds 1, 3, and 6 were potent stimulants of NGF release with stimulation levels of 151.74 ± 6.77%, 144.31 ± 7.49%, and 167.61 ± 18.5%, respectively. PMID:25894905

  16. Flavonoid glycosides from Chromolaena odorata leaves and their in vitro cytotoxic activity.

    PubMed

    Hung, Tran Manh; Cuong, To Dao; Dang, Nguyen Hai; Zhu, Shu; Long, Pham Quoc; Komatsu, Katsuko; Min, Byung Sun

    2011-01-01

    Two new flavonoid glycosides, (1, 2), and eleven known compounds, (3-13), were isolated from from a 70% EtOH extract of the leaves of Chromolaena odorata (Asteraceae). Their structures were elucidated by 1D and 2D NMR spectroscopic interpretation as well as by chemical studies. The newly isolated compounds were tested in vitro for their cytotoxic activities against the LLC and HL-60 cancer cell lines. Compound 1 showed cytotoxicity against LLC and HL-60 cancer cell lines with IC(50) values of 28.2 and 11.6 µM, respectively. Compound 2 exhibited significant cytotoxic activity in the inhibition of HL-60 cancer cell lines with IC(50) value of 10.8 µM. PMID:21212562

  17. A new flavanone glycoside from the dried immature fruits of Poncirus trifoliata.

    PubMed

    Han, Ah-Reum; Kim, Jong-Bin; Lee, Jun; Nam, Joo-Won; Lee, Ik-Soo; Shim, Chang-Koo; Lee, Kyung-Tae; Seo, Eun-Kyoung

    2007-08-01

    A new flavanone glycoside, (2R)-5-hydroxy-4'-methoxyflavanone-7-O-{beta-glucopyranosyl-(1-->2)-beta-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E(2) (PGE(2)) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells. PMID:17666859

  18. A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora.

    PubMed

    Ho, Duc Viet; Kodama, Takeshi; Le, Hien Thi Bich; Phan, Kiem Van; Do, Thao Thi; Bui, Tai Huu; Le, Anh Tuan; Win, Nwet Nwet; Imagawa, Hiroshi; Ito, Takuya; Morita, Hiroyuki; Nguyen, Hoai Thi

    2015-08-15

    A new polyoxygenated cyclohexene, (-)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvaria grandiflora collected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3-6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11-12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for 1, and chemical conversion for 2. Compound 1 exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC50 values of 4.68 and 3.63?M, respectively. Remarkably, the cytotoxicity of 12 against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC50 values ranging from 1.24 to 1.60?M. PMID:26077495

  19. Structural elucidation of two new megastigmane glycosides from the leaves of AquiAquilaria sinensi.

    PubMed

    Sun, Jian; Xia, Fang; Wang, Shu; Wang, Ke-Yuan; Chen, Jin-Ming; Tu, Peng-Fei

    2015-04-01

    The present study was designed to determine the chemical constituents and identify new components of the leaves of Aquilaria sinensis (Lour.) Gilg. The compounds were isolated and purified by repeated silica gel, Sephadex LH-20, and ODS column chromatography and their structures were elucidated by NMR and HR-ESI-MS spectrometry. Eight megastigmane glycosides and two cucurbitacins were isolated and identified as (9S) megastigma-4,7-diene-2,3,9-triol 9-O-?-D-glucopyranoside (1), (9S) megastigma-4(13),7-diene-3,6,9-triol 9-O-?-D-glucopyranoside (2), macarangloside D (3), corchoionoside C (4), staphylionoside H (5), (+) 3-oxo-?-ionol-?-D-glucopyranoside (6), (-) 3-oxo-?-ionol-?-D-glucopyranoside (7), citroside B (8), 2-O-?-D-glucopyranosyl cucurbitacin I (9), bryoamaride (10). Compounds 1 and 2 were newly identified megstigmane glucosides and reported from this genus for the first time. PMID:25908626

  20. Reactive oxygen species scavenging activity of flavone glycosides from Melilotus neapolitana.

    PubMed

    Fiorentino, Antonio; D'Abrosca, Brigida; Pacifico, Severina; Golino, Annunziata; Mastellone, Claudio; Oriano, Palma; Monaco, Pietro

    2007-01-01

    One new and six known flavone glycosides were isolated from the MeOH extract of Melilotus neapolitana Ten. The new compound, identified as 7-O-beta-D-glucopyranosyloxy-4',5-dihydroxy-3-[O-alpha-L-rhamnopyranosyl-(1-->6)-3-O-beta-D-glucopyranosyloxy]flavone (1) by 1D and 2D NMR techniques and mass spectra, was isolated along with kaempferol-3-O-rutinoside (2), kaempferol-3-O-glucoside (3), rutin (4), quercetin-3-O-glucoside (5), isorhamnetin-3-O-rutinoside (6), and isorhamnetin-3-O-glucoside (7). The antioxidant and radical scavenging activities of these compounds and the whole crude methanol extract were evaluated. The organic extract can inhibit MDA marker's synthesis by 57%. All the metabolites displayed good reducing power, with the kaempferol (2,3) and isorhamnetin derivatives (6,7) being less active than the corresponding quercetin derivatives 4,5. PMID:17846577

  1. Characterisation of free and glycosidically bound aroma compounds of La Mancha Verdejo white wines.

    PubMed

    Sánchez-Palomo, E; Alonso-Villegas, R; González Vińas, M A

    2015-04-15

    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

  2. Targeting Anthracycline-Resistant Tumor Cells with Synthetic Aloe-Emodin Glycosides

    PubMed Central

    2011-01-01

    The cytotoxic activity of aloe-emodin (AE), a natural anthranoid that readily permeates anthracycline-resistant tumor cells, was improved by the attachment of an amino-sugar unit to its anthraquinone core. The new class of AE glycosides (AEGs) showed a significant improvement in cytotoxicity—up to more than 2 orders of magnitude greater than those of AE and the clinically used anthracycline doxorubicin (DOX)—against several cancer cell lines with different levels of DOX resistance. Incubation with the synthetic AEGs induced cell death in less than one cell cycle, indicating that these compounds do not directly target the cell division mechanism. Confocal microscopy provided evidence that unlike DOX, AEGs accumulated in anthracycline-resistant tumor cells in which resistance is conferred by P-glycoprotein efflux pumps. The results of this study demonstrate that AEGs may serve as a promising scaffold for the development of cytotoxic agents capable of overcoming anthracycline resistance in tumor cells. PMID:24900344

  3. A new antibacterial octaketide and cytotoxic phenylethanoid glycosides from Pogostemon cablin (Blanco) Benth.

    PubMed

    Kim, Ki Hyun; Beemelmanns, Christine; Clardy, Jon; Cao, Shugeng

    2015-07-15

    A new octaketide, named cytosporone V (1), and two other known phenylethanoid glycosides (2-3), were isolated from the aerial parts of Pogostemon cablin (Blanco) Benth. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including extensive 2D NMR and HR-MS. Compounds 1-3 displayed weak antibacterial activity against two gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus. All isolates were also evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 2 and 3 showed significant cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines with IC50 values ranging from 2.73 to 9.52?M. PMID:25981688

  4. New bioactive flavonoid glycosides isolated from the seeds of Lepidium apetalum Willd.

    PubMed

    Shi, Pingping; Chao, Liping; Wang, Tingtxing; Liu, Erwei; Han, Lifeng; Zong, Qi; Li, Xiaoxia; Zhang, Yi; Wang, Tao

    2015-06-01

    Ten flavonoid glycosides, apetalumosides A (1), B1-B7 (2-8), and C (9), quercetin 3-O-(2,6-di-O-?-d-glucopyranosyl)-?-d-glucopyranoside (10), were obtained from the seeds of Lepidium apetalum Willd. Their structures were elucidated by chemical and spectroscopic methods (UV, IR, NMR, and HRESI-TOF-MS). 1-9 were new isolates. The NMR data for 10 was reported here for the first time. On the other hand, activity screening results showed that 1-3 and 10 had triglyceride accumulation inhibitory effects in HepG2 cells. Preliminary structure-activity relationship study revealed that 7-hydroxyl group is an essential moiety. PMID:25869847

  5. Extraction of Cs-137 by alcohol-water solvents from plants containing cardiac glycosides

    E-print Network

    Dzyubak, S N; Dzyubak, O P; Sorokin, P V; Popov, V F; Orlov, A A; Krasnov, V P; Gubin, Yu.I.

    2001-01-01

    As a result of nuclear power plant accidents, large areas receive radioactive inputs of Cs-137. This cesium accumulates in herbs growing in such territories. The problem is whether the herbs contaminated by radiocesium may be used as a raw material for medicine. The answer depends on the amount of Cs-137 transfered from the contaminated raw material to the medicine. We have presented new results of the transfer of Cs-137 from contaminated Digitalis grandiflora Mill. and Convallaria majalis L. to medicine. We found that the extraction of Cs-137 depends strongly on the hydrophilicity of the solvent. For example 96.5%(vol.) ethyl alcohol extracts less Cs-137 (11.6%) than 40%(vol.) ethyl alcohol or pure water (66.2%). The solubility of the cardiac glycosides is inverse to the solubility of cesium, which may be of use in the technological processes for manufacturing ecologically pure herbal medicine.

  6. Isolation and structural characterization of a new minor diterpene glycoside from Stevia rebaudiana.

    PubMed

    Chaturvedula, Venkata Sai Prakash; Zamora, Julian

    2014-12-01

    From the commercial extract of the leaves of the sweet plant Stevia rebaudiana Bertoni obtained from Sinochem Qingdao Co. Ltd., a new diterpene glycoside having three ?-D-glucopyranosyl units of which two of them were connected in a relatively rare linkage of 3-?-D-glucobiosyl substitution at C-19 position of the aglycone steviol. The structure of the new compound has been characterized as 13-?-D-glucopyranosyloxy ent-kaur-16-en-19-oic acid-[(3-O-?-D- glucopyranosyl-?-D-glucopyranosyl) ester (1) on the basis of extensive 1D (1H and 13C) and 2D NMR (TOCSY, HMQC, and HMBC), and High Resolution mass spectroscopic data as well as hydrolysis studies. PMID:25632456

  7. Isolation and HPLC quantitative analysis of flavonoid glycosides from Brazilian beverages (Maytenus ilicifolia and M. aquifolium).

    PubMed

    Leite, J P; Rastrelli, L; Romussi, G; Oliveira, A B; Vilegas, J H; Vilegas, W; Pizza, C

    2001-08-01

    Aqueous infusions of Brazilian Maytenus leaves are used as beverages, foodstuffs, and phytomedicines. Previously, we isolated two new flavonoid tetrasaccharides from the infusion of Maytenus aquifolium leaves that showed antiulcer activity. In this investigation a new flavonoid tetrasaccharide, kaempferol-3-O-alpha-L-rhamnopyranosyl (1-->6)-O-[alpha-L-arabinopyranosyl (1-->3)-O-alpha-L-rhamnopyranosyl (1-->2)]-O-beta-D-galactopyranoside (3), was isolated, together with kaempferol tri- and disaccharides and quercetin trisaccharides from the aqueous infusion of Maytenus ilicifolia leaves. All structures were elucidated by ES-MS and NMR spectroscopic methods. The quantitative analysis of the flavonoid glycosides from Maytenus ilicifolia and M. aquifolium has been performed by HPLC. PMID:11513669

  8. Enzymatic acylation of flavonoid glycosides by a carbohydrate esterase of family 16.

    PubMed

    Biely, Peter; Cziszárová, Mária; Wong, Ken K Y; Fernyhough, Alan

    2014-11-01

    The acetyl esterase of Trichoderma reesei belonging to carbohydrate esterase (CE) family 16 catalyzes transacylations to carbohydrate moieties of flavonoid glycosides, esculin and rutin. The enzyme recognizes as acyl donors vinyl esters of short carboxylic acids. Esculin was acylated at position 3 of the glucosyl residue in aqueous solutions saturated with vinyl acetate and vinyl propionate. The yields of esculin monoacetate and monopropionate of esculin in aqueous medium (esculin 40 mM, enzyme 40 µg/ml, 40 °C, 3 days) were 67 and 55 %, respectively. Replacement of water by 2-propanol was required for a similar acylation of rutin at 4 mM concentration. The yields of rutin monoacetate and propionate were 60 and 30 %, respectively. The results indicate that the enzyme could be used for an easy modification of solubility and hydrophobicity of glycosylated compounds, including drugs and functional food additives. PMID:25048225

  9. Construction of a rice glycoside hydrolase phylogenomic database and identification of targets for biofuel research

    PubMed Central

    Sharma, Rita; Cao, Peijian; Jung, Ki-Hong; Sharma, Manoj K.; Ronald, Pamela C.

    2013-01-01

    Glycoside hydrolases (GH) catalyze the hydrolysis of glycosidic bonds in cell wall polymers and can have major effects on cell wall architecture. Taking advantage of the massive datasets available in public databases, we have constructed a rice phylogenomic database of GHs (http://ricephylogenomics.ucdavis.edu/cellwalls/gh/). This database integrates multiple data types including the structural features, orthologous relationships, mutant availability, and gene expression patterns for each GH family in a phylogenomic context. The rice genome encodes 437 GH genes classified into 34 families. Based on pairwise comparison with eight dicot and four monocot genomes, we identified 138 GH genes that are highly diverged between monocots and dicots, 57 of which have diverged further in rice as compared with four monocot genomes scanned in this study. Chromosomal localization and expression analysis suggest a role for both whole-genome and localized gene duplications in expansion and diversification of GH families in rice. We examined the meta-profiles of expression patterns of GH genes in twenty different anatomical tissues of rice. Transcripts of 51 genes exhibit tissue or developmental stage-preferential expression, whereas, seventeen other genes preferentially accumulate in actively growing tissues. When queried in RiceNet, a probabilistic functional gene network that facilitates functional gene predictions, nine out of seventeen genes form a regulatory network with the well-characterized genes involved in biosynthesis of cell wall polymers including cellulose synthase and cellulose synthase-like genes of rice. Two-thirds of the GH genes in rice are up regulated in response to biotic and abiotic stress treatments indicating a role in stress adaptation. Our analyses identify potential GH targets for cell wall modification. PMID:23986771

  10. Inhibition of epidermal growth factor signaling by the cardiac glycoside ouabain in medulloblastoma

    PubMed Central

    Wolle, Daniel; Lee, Seung Joon; Li, Zhiqin; Litan, Alisa; Barwe, Sonali P; Langhans, Sigrid A

    2014-01-01

    Epidermal growth factor (EGF) signaling regulates cell growth, proliferation, and differentiation. Upon receptor binding, EGF triggers cascades of downstream signaling, including the MAPK and phosphoinositide-3-kinase (PI3K)/Akt signaling pathways. Aberrant expression/activation of EGFR is found in multiple human cancers, including medulloblastoma, the most prevalent pediatric brain cancer, and often has been associated with metastasis, poor prognosis, and resistance to chemotherapy. Na,K-ATPase is an ion pump well known for its role in intracellular ion homeostasis. Recent studies showed that Na,K-ATPase also functions as a signaling platform and revealed a role in EGFR, MAPK, and PI3K signaling. While both EGFR and Na,K-ATPase seem to modulate similar signaling pathways, cardiac glycosides that are steroid-like inhibitors of Na,K-ATPase, exhibit antiproliferative and proapoptotic properties in cancer cells. Thus, we sought to better understand the relationship between EGF and cardiac glycoside signaling. Here, we show that in medulloblastoma cells, both EGF and ouabain activate Erk1/2 and PI3K/Akt signaling. Nevertheless, in medulloblastoma cells ouabain did not transactivate EGFR as has been reported in various other cell lines. Indeed, ouabain inhibited EGF-induced Erk1/2 and Akt activation and, moreover, prevented EGF-induced formation of actin stress fibers and cell motility, probably by activating a stress signaling response. Na,K-ATPase has been proposed to act as a signaling scaffold and our studies suggest that in medulloblastoma cells Na,K-ATPase might act as a check point to integrate EGF-associated signaling pathways. Thus, Na,K-ATPase might serve as a valid target to develop novel therapeutic approaches in tumors with aberrant activation of the EGFR signaling cascades. PMID:25052069

  11. Aspects of glycosidic bond formation in aqueous solution: chemical bonding and the role of water.

    PubMed

    Stubbs, John M; Marx, Dominik

    2005-04-22

    A model of the specific acid-catalyzed glycosidic bond formation in liquid water at ambient conditions is studied based on constrained Car-Parrinello ab initio molecular dynamics. Specifically the reaction of alpha-D-glucopyranose and methanol is found to proceed by a D(N)A(N) mechanism. The D(N) step consists of a concerted protonation of the O(1) hydroxyl leaving group; this process results in the breaking of the C(1)-O(1) bond, and oxocarbenium ion formation involving C(1)=O(5). The second step, A(N), is the formation of the C(1)-O(m) glycosidic bond, deprotonation of the methanol hydroxyl group O(m)H(m), and re-formation of the C(1)-O(5) single bond. A focus of this study is the analysis of the electronic structure during this condensed phase reaction relying on both Boys/Wannier localized orbitals and the electron localization function ELF. This analysis allows the clear elucidation of the chemical bonding features of the intermediate bracketed by the D(N) and A(N) steps, which is a non-solvent equilibrated oxocarbenium cation. Most interestingly, it is found that the oxygen in the pyranose ring becomes "desolvated" upon double bond/oxocarbenium formation, whereas it is engaged in the hydrogen-bonded water network before and after this period. This demonstrates that hydrogen bonding and thus the aqueous solvent play an active role in this reaction implying that microsolvation studies in the gas phase, both theoretical and experimental, might lead to qualitatively different reaction mechanisms compared to solution. PMID:15729673

  12. A new bioactive flavone glycoside from the seeds of Melilotus indica All.

    PubMed

    Yadava, R N; Jain, S

    2005-08-01

    Melilotus indica All. [Chopra, R.N., Nayar, S.L. and Chopra, I.C. (1956) Glossary Indian Med. Plants, 164 C.S.I.R. Publication New-Delhi; Kirtikar, K.R. and Basu, B.D. (1935) Indian Medicinal Plants, 2nd Ed., Vol. I, pp. 703-704 Lalit Mohan Basuan Co. Allahabad. The Wealth of India (1962) A Dictionary of Raw Materials and Industrial Products, Vol. VI, pp. 329-331 (C.S.I.R. Publication: New-Delhi)] belongs to family Leguminosae, which is commonly known as 'Banmethi' in Hindi. It is found in North India, extending into S. Persia, S. Europe and the Tropical zone of India. The seeds are used as an anthelmintic, an antipyretic, for curing heart diseases, bronchitis, leprosy, bowel complaints and infantile diarrhea. The plant has also been used as a discutient, emollient, and as a fomentation. It is also useful in a plaster for swelling. It is considered astringent and narcotic. Earlier workers have reported the presence of C-glycosides [Sayed, E.L., Ishak, M.S. and Mabry, T.J. (1997) Asian J. Chem., 9, 551], methylene-dioxypterocarpan (MIS6) [Saxena, V.K. and Nigam, S. (1997) Fitoterapia, 68, 343-345], pterocarpane (MIS2) [Saxena, V.K. and Nigam, S. (1996) J. Institution Chem. 68, 122-125] and prenylated pterocarpan [Saxena, V.K. and Nigam, S. (1997) Fitoterapia, 68, 403-407] from this plant. Here, we report the isolation of the new flavone glycoside 5,7,4'-trihydroxy-6,3'-dimethoxyflavone-7-O-alpha-L-arabinopyranosyl(1-->6)-O-beta-D-galactopyranoside (1) from the seeds of this plant. PMID:16087633

  13. Metabolomics of plant saponins: bioprospecting triterpene glycoside diversity with respect to mammalian cell targets.

    PubMed

    Joshi, Lokesh; Van Eck, Joyce M; Mayo, Kristin; Di Silvestro, Regina; Blake Nieto, Mary E; Ganapathi, Thumballi; Haridas, Valsala; Gutterman, Jordan U; Arntzen, Charles J

    2002-01-01

    One of the goals of cancer chemotherapy and prevention is the discovery of compounds that are relatively selective to tumor cells and, therefore, have reduced effects on normal cell growth. In previously published studies, it was shown that certain triterpene saponins (called avicins) from a desert tree, Acacia victoriae, are selectively toxic to tumor cells at very low doses (IC(50): 0.2 microg/mL for Jurkat cells). To extend this research to human clinical studies, we needed to find a reliable supply of avicins and have developed a transformed "hairy root" culture as a means of biomass production. Protocols were optimized for A. victoriae micropropagation; after a boiling water treatment, A. victoriae seeds were maintained under in vitro conditions on defined media. Embryo-axis explants from shoot tips were removed and infected with Agrobacterium rhizogenes Conn (R 1000) for hairy root induction. Plasmid integration was confirmed by PCR analysis with a primer set for a segment of the rol B gene. Culture conditions have been optimized for root biomass production, and various inducers have been investigated for enhancement of avicin production. Hairy root cultures were compared with intact pod tissue from field-grown sources for avicin content following partial purification of triterpene glycosides and HPLC separation of the secondary metabolites. From bioassays of the collected HPLC fractions, we have identified putative triterpene "metabolic clusters" with enhanced activity against tumor cells. This now provides a system for both production of clinical trial lots of active samples, but also a means to correlate structure of individual triterpene glycosides with specific cellular target activity in mammalian cells. PMID:12427275

  14. Characterizing the catalyzed hydrolysis of ?-1,4 glycosidic bonds using density functional theory.

    PubMed

    Fleming, Kelly L; Pfaendtner, Jim

    2013-12-27

    Unraveling the mechanistic details of biomass deconstruction at ambient conditions has remained a challenge for many years. In this study we examine a crucial step in the pretreatment of biomass: the hydrolytic cleavage of the glycosidic bond present in many forms of biomass and other oligomeric saccharides. We present the detailed mechanistic steps found using density functional theory and transition state calculations on the acid catalyzed hydrolysis of a pyranose dimer linked by a ?-1,4 glycosidic bond in a vacuum and various continuum solvation models. The order that the bonds in the double displacement reaction form and break was revealed along with the transition state energies and an overall intrinsic reaction pathway for the two-step mechanism. The uncatalyzed hydrolysis reaction, mediated by a single water splitting event, was also determined with DFT calculations and a detailed comparison to the two-step catalyzed reaction was performed. The effects of the surrounding solvent on the reaction energetics were studied by systematically changing the dielectric strength and polarity of the solvent model. For acidic solvents, a trend was observed that related the transition state energy barrier to the inverse of the dielectric constant whereas solvents that varied slightly in dielectric strength but strongly in polarity (e.g., alcohols) did not significantly change the reaction energetics. The effects of the substituents on the model sugar were also studied by changing from a model pyranose dimer to xylobiose and cellobiose. Irrespective of the solvent choice or model sugar characteristics we observed identical ordering of all bond breaking/forming in both transition states in the double displacement mechanism. PMID:24266504

  15. Hypothalamic sodium-transport inhibitor is a high-affinity reversible inhibitor of Na+-K+-ATPase.

    PubMed

    Haupert, G T; Carilli, C T; Cantley, L C

    1984-12-01

    Bovine hypothalamus contains a stable, low molecular weight substance with ouabain-like properties. To further study its mechanism of action and potential physiological importance we examined its effects on purified Na+-K+-ATPase in a kinetic coupled-enzyme assay. Under optimal conditions up to 95% of Na+-K+-ATPase activity could be inhibited by the factor. Mg2+ is required for maximal inhibitory activity, but ligand requirements for optimal activity are otherwise distinct from those of both ouabain and vanadate. Inhibition is reversed by high concentrations of sodium chloride plus EDTA. Kinetic analysis yielded a Ki = 1.4 nM. The hypothalamic factor is a high-affinity reversible inhibitor of Na+-K+-ATPase, being at least as potent as the cardiac glycoside ouabain and may be a circulating inhibitor of sodium transport, which appears to be associated with experimental volume-expanded hypertension and human essential hypertension. PMID:6095682

  16. Geomagnetic Field During a Reversal

    NASA Technical Reports Server (NTRS)

    Heirtzler, J. R.

    2003-01-01

    It has frequently been suggested that only the geomagnetic dipole, rather than higher order poles, reverse during a geomagnetic field reversal. Under this assumption the geomagnetic field strength has been calculated for the surface of the Earth for various steps of the reversal process. Even without an eminent a reversal of the field, extrapolation of the present secular change (although problematic) shows that the field strength may become zero in some geographic areas within a few hundred years.

  17. Gridded electron reversal ionizer

    NASA Technical Reports Server (NTRS)

    Chutjian, Ara (Inventor)

    1993-01-01

    A gridded electron reversal ionizer forms a three dimensional cloud of zero or near-zero energy electrons in a cavity within a filament structure surrounding a central electrode having holes through which the sample gas, at reduced pressure, enters an elongated reversal volume. The resultant negative ion stream is applied to a mass analyzer. The reduced electron and ion space-charge limitations of this configuration enhances detection sensitivity for material to be detected by electron attachment, such as narcotic and explosive vapors. Positive ions may be generated by generating electrons having a higher energy, sufficient to ionize the target gas and pulsing the grid negative to stop the electron flow and pulsing the extraction aperture positive to draw out the positive ions.

  18. Reversed field pinch diagnostics

    SciTech Connect

    Weber, P.G.

    1986-01-01

    The Reversed Field Pinch (RFP) is a toroidal, axisymmetric magnetic confinement configuration characterized by a magnetic field configuration in which the toroidal magnetic field is of similar strength to the poloidal field, and is reversed at the edge compared to the center. The RFP routinely operates at high beta, and is a strong candidate for a compact fusion device. Relevant attributes of the configuration will be presented, together with an overview of present and planned experiments and their diagnostics. RFP diagnostics are in many ways similar to those of other magnetic confinement devices (such as tokamaks); these lectures will point out pertinent differences, and will present some diagnostics which provide special insights into unique attributes of the RFP.

  19. Time reversal of wideband microwaves

    Microsoft Academic Search

    G. Lerosey; J. de Rosny; A. Tourin; A. Derode; M. Fink

    2006-01-01

    In this letter, time reversal is applied to wideband electromagnetic waves in a reverberant room. To that end a multiantenna time reversal mirror (TRM) has been built. A 150 MHz bandwidth pulse at a central frequency of 2.45 GHz is radiated by a monopolar antenna, spread in time due to reverberation, recorded at the TRM, time reversed, and retransmitted. The

  20. Enriching Reverse Engineering with Annotations

    E-print Network

    Nierstrasz, Oscar

    Enriching Reverse Engineering with Annotations Andrea Br¨uhlmann, Tudor G^irba, Orla Greevy, Oscar to capture such knowledge during the reverse engineering process. Annotation types can be iteratively defined approach supports reverse engineering by implement- ing it in a tool called Metanool and by applying