Sample records for iridoid glucoside aucubin

  1. Iridoid glucosides from Plantago cornuti, Plantago major and Veronica cymbalaria

    Microsoft Academic Search

    Rilka Taskova; Nedjalka Handjieva; Ljubka Evstatieva; Simeon Popov

    1999-01-01

    The new iridoid glucoside from the rare ?8,9 type, 10-acetoxymajoroside, was isolated from Plantago cornuti and P. major along with known iridoids. The main constituents in V. cymbalaria were the known catalpol, amphicoside and verproside together with alpinoside, aucubin, 6-O-veratroylcatalpol and verminoside. The iridoid alpinoside with a 8,9-double bond was found for the first time in genus Veronica.

  2. Phytotoxic Iridoid Glucosides from the Roots of Verbascum thapsus

    Microsoft Academic Search

    F. Pardo; F. Perich; R. Torres; F. Delle Monache

    1998-01-01

    The iridoid glucosides lateroside 1, harpagoside 2, ajugol 3, and aucubin 4 were isolated from an ethanolic extract of the roots of the weed Verbascum thapsus that exhibits antigermination activity on seeds of barley (Hordeum vulgare). Bioassays indicated that at 3 mM concentration, compounds 1, 2, and 4 showed moderate inhibition of seed germination. These compounds also reduced root length

  3. Iridoid Glucosides and an Acetophenone Glucoside from Penstemon whippleanus.

    PubMed

    Junior, P

    1984-10-01

    From leaves of PENSTEMON WHIPPLEANUS A. Gray three iridoid glucosides and an acetophenone glucoside have been isolated which were proved to be 10- T-cinnamoylaucubin, eurostoside, mussaenoside and picein, respectively. PMID:17340348

  4. [Iso-Scrophularioside, a new iridoid glucoside from Penstemon eriantherus].

    PubMed

    Junior, P

    1981-09-01

    From the aerial parts of Penstemon eriantherus Pursh a new iridoid glucoside was isolated and structurally elucidated as 10-cinnamoylaucubin mainly by spectroscopic methods ( (1)-NMR, (13)-NMR, MS). PMID:17402005

  5. Lantanoside, a monocyclic C 10 iridoid glucoside from viburnum lantana

    Microsoft Academic Search

    Heinz Rüegger; Anthony D. Wright; Otto Sticher

    1995-01-01

    A new monocyclic C10 iridoid glucoside was isolated from the leaves of Viburnum lantana, together with the two known glucosides, dihydropenstemide and betulalbuside A. The structure of the new compound, lantanoside, was established from extensive 1H and 13C NMR, 1D and 2D homo-and heteronuclear correlation experiments.

  6. Acylated iridoid glucosides from Veronica anagallis-aquatica

    Microsoft Academic Search

    U. Sebnem Harput; Mehtap Varel; Akito Nagatsu; Iclal Saracoglu

    2004-01-01

    Three new (1–3) and four known iridoid glucosides (4–7) as well as a known phenylethanoid glycoside (8) were isolated from the aerial parts of Veronica anagallis-aquatica and their structures were determined as 6?-O-benzoyl-8-epiloganic acid named aquaticoside A (1), 6?-O-p-hydroxybenzoyl-8-epiloganic acid named aquaticoside B (2), 6?-O-benzoyl-gardoside named aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8)

  7. Inhibitory Potencies of Several Iridoids on Cyclooxygenase1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis Factor-? and Nitric Oxide Production In Vitro

    Microsoft Academic Search

    Kyoung Sik Park; Bong Hyun Kim; Il-Moo Chang

    2010-01-01

    To verify the anti-inflammatory potency of iridoids, seven iridoid glucosides (aucubin, catalpol, gentiopicroside, swertiamarin, geniposide, geniposidic acid and loganin) and an iridoid aglycone (genipin) were investigated with in vitro testing model systems based on inhibition of cyclooxygenase (COX)-1\\/-2 enzymes, the tumor necrosis factor-a (TNF-a) formation and nitric oxide (NO) production. The hydrolyzed-iridoid products (H-iridoid) with b-gludosidase treatment only showed inhibitory

  8. Acylated iridoid glucosides from Veronica anagallis-aquatica.

    PubMed

    Harput, U Sebnem; Varel, Mehtap; Nagatsu, Akito; Saracoglu, Iclal

    2004-07-01

    Three new (1-3) and four known iridoid glucosides (4-7) as well as a known phenylethanoid glycoside (8) were isolated from the aerial parts of Veronica anagallis-aquatica and their structures were determined as 6'-O-benzoyl-8-epiloganic acid named aquaticoside A (1), 6'-O-p-hydroxybenzoyl-8-epiloganic acid named aquaticoside B (2), 6'-O-benzoyl-gardoside named aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) on the basis of 1D and 2D NMR spectral analysis. PMID:15279985

  9. Iridoid glucosides in the endemic Picconia azorica (Oleaceae).

    PubMed

    Gousiadou, Chrysoula; Kokubun, Tetsuo; Martins, José; Gotfredsen, Charlotte H; Jensen, Søren R

    2015-07-01

    In our continued investigation of plants from the family Oleaceae we have now investigated Picconia azorica endemic to the Azores. Like most species within the family it contains the oleoside-based secoiridoid glucosides ligstroside and oleuropein as the main compounds and in addition verbascoside and echinacoside. As with the previously investigated Picconia excelsa, it also contained the carbocyclic iridoid glucosides involved in the biosynthetic pathway to the oleoside derivatives. However, while P. excelsa contained loganin esterified with some monoterpenoid acids, P. azorica contains similar esters of 7-epi-loganic acid named Picconioside A and B. In addition were found the two 7-O-E/Z-cinnamoyl esters of 7-epi-loganic acid named Picconioside C and D. PMID:25687603

  10. Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.

    PubMed

    Opitz, Sebastian E W; Jensen, Søren R; Müller, Caroline

    2010-02-01

    In this study, the larval sequestration abilities and defense effectiveness of four sawfly species of the genus Athalia (Hymenoptera: Tenthredinidae) that feed as larvae either on members of the Brassicaceae or Plantaginaceae were investigated. Brassicaceae are characterized by glucosinolates (GLSs), whereas Plantaginaceae contain iridoid glucosides (IGs) as characteristic secondary compounds. Athalia rosae and A. liberta feed on members of the Brassicaceae. Larvae of A. rosae sequester aromatic and aliphatic GLSs of Sinapis alba in their hemolymph, as shown previously, but no indolic GLSs; A. liberta larvae with a narrower host range sequester aliphatic as well as indolic GLSs from their host plant Alliaria petiolata. Larvae of A. circularis and A. cordata are specialized on members of the Plantaginaceae. Athalia circularis utilizes mainly Veronica beccabunga as host plant, whereas A. cordata feeds additionally on Plantago lanceolata. Both sawfly species sequester the IGs aucubin and catalpol. In V. beccabunga, catalpol esters and carboxylated IGs also occur. The high catalpol concentrations in hemolymph of A. circularis can only be explained by a metabolization of catalpol esters and subsequent uptake of the resulting catalpol. The carboxylated IGs of the plant are excreted. The IG-sequestering sawfly species are able to accumulate much higher glucoside concentrations in their hemolymph than the GLS-sequestering species, and the concentration of IGs in hemolymph increases constantly during larval development. The defensive effectiveness of hemolymph that contains GLSs or IGs and of the respective glucosides was tested in feeding-bioassays against a potential predator, the ant Myrmica rubra (Hymenoptera: Formicidae). Hemolymph of IG-sequestering cryptic A. cordata larvae has a higher deterrence potential than hemolymph of the GLS-sequestering conspicuous A. rosae larvae. The results show that glucoside sequestration is widespread in the genus Athalia, but that the specific glucoside uptake can result in different defense effectiveness against a predator species. PMID:20127151

  11. Alkaline phosphatase (ALP) enhancing iridoid glucosides from the Indonesian medicinal plant Barleria lupulina.

    PubMed

    Widyowati, Retno; Tezuka, Yasuhiro; Miyahara, Tatsurou; Awale, Suresh; Kadota, Shigetoshi

    2010-11-01

    In order to find antiosteoporotic agents from natural resources, 32 Indonesian medicinal plants were screened for their effects on osteoblast differentiation by using alkaline phosphatase (ALP) activity in MC3T3-E1 osteoblast cells as a marker. From the extract of Barleria lupulina, which showed the most potent activity, 13 iridoid glucosides, including three new ones [8-O-acetylipolamiidic acid (1), 8-O-acetyl-6-O-(p-methoxy-cis-cinnamoyl)shanzhiside (2), and 8-O-acetyl-6-O-(p-methoxy-trans-cinnamoyl)shanzhiside (3)] were identified. Among the 13 iridoid glucosides, ipolamiide (4) showed the most potent activity in a dose-dependent manner. PMID:21213964

  12. Caeruleosides A and B, bis-iridoid glucosides from Lonicera caerulea

    Microsoft Academic Search

    Koichi Machida; Junko Asano; Masao Kikuchi

    1995-01-01

    Two new bis-iridoid glucosides, named caeruleosides A and B, were isolated from the leaves of Lonicera caerulea. Their structures have been determined by chemical methods and by 1D and 2D NMR analysis. The compounds consist of secologanin attached through acetal bonds to C-4? and C-6? of the sugar part of loganin and sweroside, respectively.

  13. Iridoid glucosides and flavones from the aerial parts of Avicennia marina.

    PubMed

    Feng, Yan; Li, Xiao-Ming; Duan, Xiao-Juan; Wang, Bin-Gui

    2006-07-01

    Two new iridoid glucosides, namely, 2'-O-[(2E,4E)-5-phenylpenta-2,4-dienoyl]mussaenosidic acid (1; mussaenosidic acid = [1S-(1alpha,4aalpha,7alpha,7aalpha)]-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid) and 2'-O-(4-methoxycinnamoyl)mussaenosidic acid (2), were isolated from the aerial parts of the mangrove plant Avicennia marina. Beside that, one known iridoid glucoside, 2'-O-coumaroylmussaenosidic acid (3) and four known flavones (flavone = 2-phenyl-4H-1-benzopyran-4-one) including 4',5-dihydroxy-3',7-dimethoxyflavone (4), 4',5-dihydroxy-3',5',7-trimethoxyflavone (5), 4',5,7-trihydroxyflavone (6), and 3',4',5-trihydroxy-7-methoxyflavone (7) were also isolated and identified. The structures of these compounds were elucidated by NMR spectroscopy and by low- and high-resolution mass spectrometry. The chemotaxonomic significance of these findings was discussed. In addition, each isolated compound was evaluated for the ability of alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity. PMID:17193312

  14. Glucosides from Vitex agnus-castus.

    PubMed

    Kuruüzüm-Uz, Ay?e; Ströch, Karsten; Demirezer, L Omür; Zeeck, Axel

    2003-08-01

    The methanolic extract of the flowering stems of Vitex agnus-castus yielded three new iridoids: 6'-O-foliamenthoylmussaenosidic acid (agnucastoside A), 6'-O-(6,7-dihydrofoliamenthoyl)mussaenosidic acid (agnucastoside B) and 7-O-trans-p-coumaroyl-6'-O-trans-caffeoyl-8-epiloganic acid (agnucastoside C) in addition to four known iridoids (aucubin, agnuside, mussaenosidic acid and 6'-O-p-hydroxybenzoylmussaenosidic acid) and one known phenylbutanone glucoside (myzodendrone). The structure elucidations were mainly done by spectroscopic methods (1D and 2D NMR spectra) and MS data interpretation. The purified compounds were tested for biological activities against various microorganisms and cancer cell lines. PMID:12895546

  15. Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica.

    PubMed

    Su, B N; Yang, L; Gao, K; Jia, Z J

    2000-04-01

    Aquaticol, an unusual bis-sesquiterpene was isolated from the medicinal plant Veronica anagallis-aquatica, in addition to 11 known compounds, aucubin, geniposidic acid, mussaenoside, catalposide, verproside, amphicoside, catalpol, boschnaloside, shanzhiside methyl ester, sitosterol and beta-stigmast-4-en-6 beta-ol-3-one. The structure of aquaticol was determined by spectroscopic means and by X-ray crystallographic analysis. PMID:10821060

  16. Aucubin Promotes Neurite Outgrowth in Neural Stem Cells and Axonal Regeneration in Sciatic Nerves

    PubMed Central

    Kim, Yong Min; Sim, U-Cheol; Shin, Yongsung

    2014-01-01

    Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities. Recently, it has been shown that aucubin prevents neuronal death in the hippocampal CA1 region in rats with diabetic encephalopathy. In addition, it has protective effects on H2O2-induced apoptosis in PC12 cells. We have shown here that aucubin promotes neuronal differentiation and neurite outgrowth in neural stem cells cultured primarily from the rat embryonic hippocampus. We also investigated whether aucubin facilitates axonal elongation in the injured peripheral nervous system. Aucubin promoted lengthening and thickness of axons and re-myelination at 3 weeks after sciatic nerve injury. These results indicate that administration of aucubin improved nerve regeneration in the rat model of sciatic nerve injury, suggesting that aucubin may be a useful therapeutic compound for the human peripheral nervous system after various nerve injuries. PMID:25258571

  17. Bioassay-guided isolation of iridoid glucosides with antinociceptive and anti-inflammatory activities from Veronica anagallis-aquatica L.

    PubMed

    Küpeli, Esra; Harput, U Sebnem; Varel, Mehtap; Yesilada, Erdem; Saracoglu, Iclal

    2005-11-14

    Extracts obtained from the herbs of various Veronica species are used as folk remedy worldwide for the treatment of various inflammatory ailments including rheumatism. In vivo anti-inflammatory and antinociceptive activities of Veronica anagallis-aquatica L. aerial parts were investigated. Methanolic extract of the plant was shown to possess significant inhibitory activity against carrageenan-induced hind paw edema model and of p-benzoquinone-induced writhings in mice. Through bioassay-guided fractionation and isolation procedures eight compounds, aquaticoside A (1), aquaticoside B (2), aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) were isolated and their structures were elucidated by spectral techniques. Catapol derivative iridoid glucosides, verproside (6) and catalposide (5), were found to possess potent antinociceptive and anti-inflammatory activities, per os without inducing any apparent acute toxicity as well as gastric damage. Results of the present study supported the utilization of the plant in Turkish folk medicine. PMID:16019176

  18. Separation and purification of water-soluble iridoid glucosides by high speed counter-current chromatography combined with macroporous resin column separation.

    PubMed

    Yue, Hui-Lan; Zhao, Xiao-Hui; Wang, Qi-Lan; Tao, Yan-Duo

    2013-10-01

    Four iridoid glucosides, shanzhiside methyl ester, phloyoside II, chlorotuberside, and penstemonoside, were isolated and purified from an herbal medicinal plant for the first time by high-speed counter-current chromatography (HSCCC) using a two-phase solvent system composed of ethyl acetate-n-butanol-water (5:14:12, v/v/v). A total of 37mg of shanzhiside methyl ester, 29mg of phloyoside II, 27mg of chlorotuberside, and 21mg of penstemonoside with the purity of 99.2%, 98.5%, 97.3%, and 99.3%, respectively, were obtained in one-step separation within 4h from 150mg of crude extract. To the best of our knowledge, this is the first report of separation and purification of iridoid glucosides from natural sources by HSCCC. The chemical structures of all the four compounds were identified by ESI-MS, (1)H NMR, and (13)C NMR. PMID:23981483

  19. A Validated HPTLC-Densitometric Method for Assay of Aucubin in Vitexagnus-castusL.

    PubMed Central

    Hajimehdipoor, Homa; Shekarchi, Maryam; PiraliHamedani, Morteza; Abedi, Zahra; Zahedi, Homeyra; Shekarchi, Maral; Gohari, Ahmad Reza

    2011-01-01

    Vitexagnus-castusL. is a medicinal plant which is used in several dosage forms for women hormonal disorders and standardized according to the iridoids or flavonoids content. Aucubin, an iridoid glycoside, considered as a marker in some formulations. In this research, a thin layer chromatographic method with densitometric detection has been developed for quantitative determination of aucubin in chaste tree fruits. Chromatographic separation was performed using silica gel high performance thin-layer chromatography (HPTLC) plates with ethyl acetate-methanol-water 77 : 15 : 8 as mobile phase. Chromatograms were visualized using p-dimethylaminobenzaldehyde as reagent. Aucubin RF-value was about 0.5 and spots were scanned at 580 nm through a mercury lamp. By using this method, the amount of aucubin was found 43.5 mg/100 g of dried plant fruits. The method was validated for selectivity, linearity (r2 = 0.997, 20-100 ?g/mL), precision (intra-day < 4.9, inter-day < 7.2) and accuracy measured via determination of recovery (95-98%). The limit of detection and limit of quantization were found 6.6 and 20 ?g/mL, respectively. This methodology was found to be precise with respect to the validation parameters. It is simple and convenient and could be applicable to the routine determination of aucubin in different Vitexagnus-castusL. samples. PMID:24250405

  20. 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

  1. 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,

  2. Iridoid and lignan glycosides from Citharexylum spinosum L

    Microsoft Academic Search

    Barbara Balázs; Gábor Tóth; Helmut Duddeck; Hesham S. M. Soliman

    2006-01-01

    From the aerial parts of Citharexylum spinosum L., one new iridoid glucoside, the 7-?-O-acetate (1) of lamiide, along with four known iridoid glucosides, lamiide (2), lamiidoside (3), duranterectoside C (4), 8-epiloganin (5) and one known lignan glucoside (+)-lyonirenisol-3a-O-?-D-glucopyranoside (6) were isolated. The compound structures were established by one- and two-dimensional H- and C-NMR as well as by ESI-MS spectra.

  3. 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

  4. Role of plant ?-glucosidases in the dual defense system of iridoid glycosides and their hydrolyzing enzymes in Plantago lanceolata and Plantago major.

    PubMed

    Pankoke, Helga; Buschmann, Torsten; Müller, Caroline

    2013-10-01

    The typical defense compounds of Plantaginaceae are the iridoid glycosides, which retard growth and/or enhance mortality of non-adapted herbivores. In plants, glycosidic defense compounds and hydrolytic enzymes often form a dual defense system, in which the glycosides are activated by the enzymes to exert biological effects. Yet, little is known about the activating enzymes in iridoid glycoside-containing plants. To examine the role of plant-derived ?-glucosidases in the dual defense system of two common plantain species, Plantago lanceolata and Plantago major, we determined the concentration of iridoid glycosides as well as the ?-glucosidase activity in leaves of different age. To investigate the presence of other leaf metabolites potentially involved in plant defense, we used a metabolic fingerprinting approach with ultra-high performance liquid chromatography coupled with time-of-flight-mass spectrometry. According to the optimal defense hypothesis, more valuable parts such as young leaves should be better protected than less valuable parts. Therefore, we expected that both, the concentrations of defense compounds as well as the ?-glucosidase activity, should be highest in younger leaves and decrease with increasing leaf age. Both species possessed ?-glucosidase activity, which hydrolyzed aucubin, one of the two most abundant iridoid glycosides in both plant species, with high activity. In line with the optimal defense hypothesis, the ?-glucosidase activity in both Plantago species as well as the concentration of defense-related metabolites such as iridoid glycosides correlated negatively to leaf age. When leaf extracts were incubated with bovine serum albumin and aucubin, SDS-PAGE revealed a protein-denaturing effect of the leaf extracts of both plantain species, suggesting that iridoid glycosides and plant ?-glucosidase interact in a dual defense system. PMID:23773298

  5. Iridoids from Symphoricarpos albus

    Microsoft Academic Search

    I. F. Makarevich; S. N. Kovalenko; T. D. Gusarova; Yu. I. Gubin

    2009-01-01

    Twelve compounds including secologanin, loganin, the aglycon of loganin, and a new iridoid called glucologanin were isolated\\u000a from fruit of common snowberry Symphoricarpos albus (L.) Blake. The structure of glucologanin was confirmed using PMR and mass spectroscopy and chemical transformations. 2?,3?,4?,6?,7-Penta-O-acetylloganin and 2?,3?,4?,6?-tetra-O-acetylloganin were synthesized.

  6. 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

  7. Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-?B signaling pathway in rat articular chondrocytes.

    PubMed

    Wang, Sheng-Nan; Xie, Guo-Ping; Qin, Cheng-He; Chen, Yi-Rong; Zhang, Kai-Rui; Li, Xue; Wu, Qian; Dong, Wei-Qiang; Yang, Jun; Yu, Bin

    2015-02-01

    Proinflammatory cytokine interleukin-1? (IL-1?) plays a crucial role in the pathogenesis of Osteoarthritis (OA) by stimulating several mediators contributed to cartilage degradation. Aucubin, a natural compound derived from plants which has been shown to possess diverse biological activities including anti-inflammatory property, may benefit the IL-1? stimulated chondrocytes. The present study was aimed to investigate the effects of Aucubin on IL-1? stimulated rat chondrocytes. Rat chondrocytes were cultured and pretreated with Aucubin (1, 10, 20, 50?M), and then stimulated with or without IL-1? (10ng/ml). Gene and protein expression of MMP-3, MMP-9, MMP-13, cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS) was determined by real-time PCR and Western blotting respectively. Nitric oxide (NO) production was quantified by Griess reagent. Phosphorylation and nuclear translocation of p65 were detected by western blotting and immunofluorescence, respectively. We found that Aucubin significantly reversed the elevated gene and protein expression of MMP-3, MMP-9, MMP-13, iNOS, COX-2 and the production of NO induced by IL-1? challenge in rat chondrocytes. Furthermore, Aucubin was able to suppress the IL-1?-mediated phosphorylation and nuclear translocation of p65, indicating Aucubin may possibly act via the NF-?B signaling pathway. The present study proposes that Aucubin may be a potential therapeutic choice in the treatment of OA due to its anti-inflammatory and chondroprotective features. PMID:25576403

  8. Iridoids from Spathodea campanulata P. Beauvais leaves.

    PubMed

    Gouda, Yaser G

    2009-06-01

    Three new and four known iridoids have been isolated from the leaves of Spathodea campanulata, the structures of the new compounds were determined as 6-O-trans-caffeoyl-decinnamoyl globularimin, 6-O-trans-caffeoyl-asystasioside E and 6-O-trans-caffeoyl-5,7-bisdeoxycynanchoside and provisionally named as spatheosides A (1), B (2) and C (3) respectively. The known iridoids were identified as verminoside (4), 6'-O-trans-caffeoyl-loganic acid (5), catalpol (6) and ajugol (7). The structures of the isolated compounds were characterized by different spectroscopic methods. PMID:19634315

  9. Selective transport systems mediate sequestration of plant glucosides in leaf beetles: A molecular basis for adaptation and evolution

    PubMed Central

    Kuhn, Jürgen; Pettersson, Eva M.; Feld, Birte K.; Burse, Antje; Termonia, Arnaud; Pasteels, Jacques M.; Boland, Wilhelm

    2004-01-01

    Chrysomeline larvae respond to disturbance and attack by everting dorsal glandular reservoirs, which release defensive secretions. The ancestral defense is based on the de novo synthesis of monoterpene iridoids. The catabolization of the host-plant O-glucoside salicin into salicylaldehyde is a character state that evolved later in two distinct lineages, which specialized on Salicaceae. By using two species producing monoterpenes (Hydrothassa marginella and Phratora laticollis) and two sequestering species (Chrysomela populi and Phratora vitellinae), we studied the molecular basis of sequestration by feeding the larvae structurally different thioglucosides resembling natural O-glucosides. Their accumulation in the defensive systems demonstrated that the larvae possess transport systems, which are evolutionarily adapted to the glycosides of their host plants. Minor structural modifications in the aglycon result in drastically reduced transport rates of the test compounds. Moreover, the ancestral iridoid-producing leaf beetles already possess a fully functional import system for an early precursor of the iridoid defenses. Our data confirm an evolutionary scenario in which, after a host-plant change, the transport system of the leaf beetles may play a pivotal role in the adaptation on new hosts by selecting plant-derived glucosides that can be channeled to the defensive system. PMID:15365181

  10. Anti-Inflammatory Iridoids of Botanical Origin

    PubMed Central

    Viljoen, A; Mncwangi, N; Vermaak, I

    2012-01-01

    Inflammation is a manifestation of a wide range of disorders which include; arthritis, atherosclerosis, Alzheimer’s disease, inflammatory bowel syndrome, physical injury and infection amongst many others. Common treatment modalities are usually non-steroidal anti-inflammatory drugs (NSAIDs) such as aspirin, paracetamol, indomethacin and ibuprofen as well as corticosteroids such as prednisone. These however, may be associated with a host of side effects due to non-selectivity for cyclooxygenase (COX) enzymes involved in inflammation and those with selectivity may be highly priced. Thus, there is a continuing search for safe and effective anti-inflammatory molecules from natural sources. Research has confirmed that iridoids exhibit promising anti-inflammatory activity which may be beneficial in the treatment of inflammation. Iridoids are secondary metabolites present in various plants, especially in species belonging to the Apocynaceae, Lamiaceae, Loganiaceae, Rubiaceae, Scrophulariaceae and Verbenaceae families. Many of these ethnobotanicals have an illustrious history of traditional use alluding to their use to treat inflammation. Although iridoids exhibit a wide range of pharmacological activities such as cardiovascular, hepatoprotection, hypoglycaemic, antimutagenic, antispasmodic, anti-tumour, antiviral, immunomodulation and purgative effects this review will acutely focus on their anti-inflammatory properties. The paper aims to present a summary for the most prominent iridoid-containing plants for which anti-inflammatory activity has been demonstrated in vitro and / or in vivo. PMID:22414102

  11. A rapid and sensitive determination of aucubin in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application.

    PubMed

    Xu, Wei; Deng, Zhipeng; Guo, Hong; Ling, Peixue

    2012-09-01

    A sensitive, accurate, rapid and robust LC-MS-MS method for the quantification of aucubin, a major bioactive constituent of Aucuba japonica, Eucommia ulmoides and Plantago asiatica, was established and validated in rat plasma. Plasma samples were simply precipitated by adding methanol and the supernatant was chromatographed by a Diamonsil® C(18)(2) column with the mobile phase comprising a mixture of 10?mm ammonium acetate in methanol and that in water with the ratio of 50:50 (v/v). Quantification of aucubin was performed by mass spectrometry in the multiple-reaction monitoring mode with positive atmospheric ionization at m/z 364???149 for aucubin, and m/z 380???165 for catalpol (IS), respectively. The retention time was 2.47 and 2.44?min for aucubin and the IS, respectively. The calibration curve (10.0-30,000?ng/mL) was linear (r² ?>?0.99) and the lower limit of quantification was 10.0?ng/mL in the rat plasma sample. The method showed satisfactory results such as sensitivity, specificity, precision, accuracy, recovery, freeze-thaw and long-term stability. This simple LC-MS method was successfully applied in a pharmacokinetic study carried out in Sprague-Dawley rats after oral administration of aucubin at a single dose of 50?mg/kg. Herein the pharmacokinetic study of aucubin is reported for the first time. PMID:22113886

  12. Eucommia ulmoides Oliver Extract, Aucubin, and Geniposide Enhance Lysosomal Activity to Regulate ER Stress and Hepatic Lipid Accumulation

    PubMed Central

    Lee, Hwa-Young; Lee, Geum-Hwa; Lee, Mi-Rin; Kim, Hye-Kyung; Kim, Nan-young; Kim, Seung-Hyun; Lee, Yong-Chul; Kim, Hyung-Ryong; Chae, Han-Jung

    2013-01-01

    Eucommia ulmoides Oliver is a natural product widely used as a dietary supplement and medicinal plant. Here, we examined the potential regulatory effects of Eucommia ulmoides Oliver extracts (EUE) on hepatic dyslipidemia and its related mechanisms by in vitro and in vivo studies. EUE and its two active constituents, aucubin and geniposide, inhibited palmitate-induced endoplasmic reticulum (ER) stress, reducing hepatic lipid accumulation through secretion of apolipoprotein B and associated triglycerides and cholesterol in human HepG2 hepatocytes. To determine how EUE diminishes the ER stress response, lysosomal and proteasomal protein degradation activities were analyzed. Although proteasomal activity was not affected, lysosomal enzyme activities including V-ATPase were significantly increased by EUE as well as aucubin and geniposide in HepG2 cells. Treatment with the V-ATPase inhibitor, bafilomycin, reversed the inhibition of ER stress, secretion of apolipoprotein B, and hepatic lipid accumulation induced by EUE or its component, aucubin or geniposide. In addition, EUE was determined to regulate hepatic dyslipidemia by enhancing lysosomal activity and to regulate ER stress in rats fed a high-fat diet. Together, these results suggest that EUE and its active components enhance lysosomal activity, resulting in decreased ER stress and hepatic dyslipidemia. PMID:24349058

  13. Extraction of citrus glucosides

    Microsoft Academic Search

    S. A. El-Nawawi

    1995-01-01

    Hesperidin and naringin were extracted from orange peel and grapefruit peel, respectively, by treating the peel with Ca(OH)2. The effect of maturity of the peel and recycling of the extracting liquor upon the yield of glucoside were investigated. The highest yields of hesperidin were obtained from orange peel extracted at the early season, increase in maturity led to a decrease

  14. Glucosides from Curculigo orchioides.

    PubMed

    Gupta, Moumita; Achari, Basudeb; Pal, Bikas C

    2005-03-01

    From the rhizomes of Curculigo orchioides two phenolic glucosides named orchiosides A and B were isolated besides four known compounds and their structures were elucidated by the combination of 2D-NMR analysis, mass spectrometry and chemical evidences. PMID:15771886

  15. Iridoids and sesquiterpenoids from the roots of Valeriana officinalis.

    PubMed

    Wang, Peng-Cheng; Hu, Jiang-Miao; Ran, Xin-Hui; Chen, Zhong-Quan; Jiang, He-Zhong; Liu, Yu-Qing; Zhou, Jun; Zhao, You-Xing

    2009-09-01

    Two new iridoids, volvaltrates A and B (1 and 2), and three new sesquiterpenoids, E-(-)-3beta,4beta-epoxyvalerenal (3), E-(-)-3beta,4beta-epoxyvalerenyl acetate (4), and mononorvalerenone (5), together with five known iridoids and two known sesquiterpenoids were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1-5 were elucidated by spectroscopic evidence. Compound 1 was an unusual iridoid with an oxygen bridge connecting C-3 and C-10, forming a cage-like structure, and compound 5 was a mononorsesquiterpenoid. PMID:19691292

  16. Phenolic glucosides from Hasseltia floribunda

    Microsoft Academic Search

    Enkhmaa Dagvadorj; Kamel H. Shaker; Donald Windsor; Bernd Schneider; Wilhelm Boland

    2010-01-01

    The leaves of Hasseltia floribunda were examined for their chemical constituents. Twelve phenolic glucosides, namely three hydroxycyclohexenyl acyl glucosides, four acylated salicortin derivatives, and five coumaroyl salicin derivatives, were isolated along with eight known phenolic glycosides, six known flavones, and two known sesquiterpenoid cyclohexenone derivatives. The structures of the isolated compounds were elucidated by NMR spectroscopic and HRMS spectrometric methods

  17. Phenolic glucosides from Hasseltia floribunda.

    PubMed

    Dagvadorj, Enkhmaa; Shaker, Kamel H; Windsor, Donald; Schneider, Bernd; Boland, Wilhelm

    2010-11-01

    The leaves of Hasseltia floribunda were examined for their chemical constituents. Twelve phenolic glucosides, namely three hydroxycyclohexenyl acyl glucosides, four acylated salicortin derivatives, and five coumaroyl salicin derivatives, were isolated along with eight known phenolic glycosides, six known flavones, and two known sesquiterpenoid cyclohexenone derivatives. The structures of the isolated compounds were elucidated by NMR spectroscopic and HRMS spectrometric methods and by comparing analytical data with those of related structures. PMID:20822782

  18. The seco-iridoid pathway from Catharanthus roseus

    PubMed Central

    Miettinen, Karel; Dong, Lemeng; Navrot, Nicolas; Schneider, Thomas; Burlat, Vincent; Pollier, Jacob; Woittiez, Lotte; van der Krol, Sander; Lugan, Raphaël; Ilc, Tina; Verpoorte, Robert; Oksman-Caldentey, Kirsi-Marja; Martinoia, Enrico; Bouwmeester, Harro; Goossens, Alain; Memelink, Johan; Werck-Reichhart, Danièle

    2014-01-01

    The (seco)iridoids and their derivatives, the monoterpenoid indole alkaloids (MIAs), form two large families of plant-derived bioactive compounds with a wide spectrum of high-value pharmacological and insect-repellent activities. Vinblastine and vincristine, MIAs used as anticancer drugs, are produced by Catharanthus roseus in extremely low levels, leading to high market prices and poor availability. Their biotechnological production is hampered by the fragmentary knowledge of their biosynthesis. Here we report the discovery of the last four missing steps of the (seco)iridoid biosynthesis pathway. Expression of the eight genes encoding this pathway, together with two genes boosting precursor formation and two downstream alkaloid biosynthesis genes, in an alternative plant host, allows the heterologous production of the complex MIA strictosidine. This confirms the functionality of all enzymes of the pathway and highlights their utility for synthetic biology programmes towards a sustainable biotechnological production of valuable (seco)iridoids and alkaloids with pharmaceutical and agricultural applications. PMID:24710322

  19. 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

  20. Journal of Chemical Ecology, Vol. 29, No. 4, April 2003 (C 2003) EFFECT OF IRIDOID GLYCOSIDE CONTENT

    E-print Network

    van Nouhuys, Saskya

    butterfly Melitaea cinxia feeds upon two host plant species in °Aland, Finland, Plantago lanceolata higher than aucubin concentrations in both host species. Plantago lanceolata individuals that were used,aucubin,catalpol,Cotesiamelitaearum,iridoidglycosides, oviposition, Melitaea cinxia, parasitism, Plantago lanceolata, Veronica spicata. INTRODUCTION Secondary

  1. 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

  2. Enzymatic Synthesis of Novel Phloretin Glucosides

    PubMed Central

    Pandey, Ramesh Prasad; Li, Tai Feng; Kim, Eun-Hee; Yamaguchi, Tokutaro; Park, Yong Il; Kim, Joong Su

    2013-01-01

    A UDP-glycosyltransferase from Bacillus licheniformis was exploited for the glycosylation of phloretin. The in vitro glycosylation reaction confirmed the production of five phloretin glucosides, including three novel glucosides. Consequently, we demonstrated the application of the same glycosyltransferase for the efficient whole-cell biocatalysis of phloretin in engineered Escherichia coli. PMID:23542617

  3. Generation of primary amide glucosides from cyanogenic glucosides.

    PubMed

    Sendker, Jandirk; Nahrstedt, Adolf

    2009-02-01

    The cyanogenic glucoside-related compound prunasinamide, (2R)-beta-d-glucopyranosyloxyacetamide, has been detected in dried, but not in fresh leaves of the prunasin-containing species Olinia ventosa, Prunus laurocerasus, Pteridium aquilinium and Holocalyx balansae. Experiments with leaves of O. ventosa indicated a connection between amide generation and an excessive production of reactive oxygen species. In vitro, the Radziszewski reaction with H(2)O(2) has been performed to yield high amounts of prunasinamide from prunasin. This reaction is suggested to produce primary amides from cyanogenic glycosides in drying and decaying leaves. Two different benzoic acid esters which may be connected to prunasin metabolism were isolated and identified as the main constituents of chlorotic leaves from O. ventosa and P. laurocerasus. PMID:19195667

  4. Bioassay-guided isolation of iridoid glucosides with antinociceptive and anti-inflammatory activities from Veronica anagallis-aquatica L

    Microsoft Academic Search

    Esra Küpeli; U. Sebnem Harput; Mehtap Varel; Erdem Yesilada; Iclal Saracoglu

    2005-01-01

    Extracts obtained from the herbs of various Veronica species are used as folk remedy worldwide for the treatment of various inflammatory ailments including rheumatism. In vivo anti-inflammatory and antinociceptive activities of Veronica anagallis-aquatica L. aerial parts were investigated. Methanolic extract of the plant was shown to possess significant inhibitory activity against carrageenan-induced hind paw edema model and of p-benzoquinone-induced writhings

  5. Anthocyanidin 3-glucoside malonyltransferase from Dahlia variabilis

    Microsoft Academic Search

    Masa-Atsu Yamaguchi; Naomi Oshida; Masayoshi Nakayama; Masaji Koshioka; Yuichi Yamaguchi; Ikuo Ino

    1999-01-01

    Cyanic flowers of Dahlia variabilis contained monomalonylated anthocyanins, 3-(6?-malonylglucoside)-5-glucosides of pelargonidin and cyanidin, and dimalonylated anthocyanins, 3,5-di(malonylglucoside)s of pelargonidin and cyanidin, in addition to nonmalonylated 3,5-diglucosides of these anthocyanidins. Enzyme extracts from this plant catalyzed the malonylation of anthocyanidin 3-glucoside to anthocyanidin 3-(6?-malonylglucoside), but not the 3,5-diglucoside to 3-(6?-malonylglucoside)-5-glucoside or 3,5-di(malonylglucoside). The amounts of this enzyme were also examined for

  6. Sesquiterpene lactone glucosides from Sonchus asper

    Microsoft Academic Search

    Amr M. Helal; Norio Nakamura; Hesham El-Askary; Masao Hattori

    2000-01-01

    From the methanolic extract of the roots of Sonchus asper, two new sesquiterpene glucosides, together with two known sesquiterpene glucosides and a known aglycone were isolated. Structures were identified as 11?,13-dihydrourospermal A, 15-O-?-D-glucopyranosyl-11?,13-dihydrourospermal A, 15-O-?-D-glucopyranosylurospermal A, 15-O-[6?-(p-hydroxyphenylacetyl)]-?-D-glucopyranosylurospermal A and 14-O-methylacetal-15-O-[6?-(p-hydroxyphenylacetyl)]-?-D-glucopyranosylurospermal A, by spectroscopic means.

  7. Host plant iridoid-based chemical defense of an aphid, Acyrthosiphon nipponicus , against ladybird beetles

    Microsoft Academic Search

    Ritsuo Nishida; Hiroshi Fukami

    1989-01-01

    A Rubiaceae-feeding aphid,Acyrthosiphon nipponicus, is seldom attacked by the ladybird beetle,Harmonia axyridis. A potent deterrent against the beetle was isolated from the aphid and identified as paederoside, an iridoid glycoside originating in the aphid's host,Paederia scandens. The iridoid content was as high as 2% of the intact body weight, and a large portion was found in the cornicle secretion.

  8. UPLC-TOF-MS Characterization and Identification of Bioactive Iridoids in Cornus mas Fruit

    PubMed Central

    West, Brett J.; Jensen, C. Jarakae

    2013-01-01

    Cornus mas L. is indigenous to Europe and parts of Asia. Although Cornus is widely considered to be an iridoid rich genera, only two iridoids have been previously found in this plant. The lack of information on taxonomically and biologically active iridoids prompted us to develop and optimize an analytical method for characterization of additional phytochemicals in C. mas fruit. An ultra performance liquid chromatography (UPLC) coupled with photodiode array spectrophotometry (PDA) and electrospray time-of-flight mass spectrometry (ESI-TOF-MS) was employed and mass parameters were optimized. Identification was made by elucidating the mass spectral data and further confirmed by comparing retention times and UV spectra of target peaks with those of reference compounds. Primary DNA damage and antigenotoxicity tests in E. coli PQ37 were used to screen the iridoids for biological activity. As a result, ten phytochemicals were identified, including iridoids loganic acid, loganin, sweroside, and cornuside. Nine of these were reported for the first time from C. mas fruit. The iridoids did not induce SOS repair of DNA, indicating a lack of genotoxic activity in E. coli PQ37. However, loganin, sweroside, and cornuside did reduce the amount of DNA damage caused by 4-nitroquinoline 1-oxide, suggesting potential antigenotoxic activity. PMID:24228188

  9. Comparison of pharmacokinetic behavior of two iridoid glycosides in rat plasma after oral administration of crude Cornus officinals and its jiuzhipin by high performance liquid chromatography triple quadrupole mass spectrometry combined with multiple reactions monitoring mode

    PubMed Central

    Chen, Xiaocheng; Cao, Gang; Jiang, Jianping

    2014-01-01

    Objective: The present study examined the pharmacokinetic profiles of two iridoid glycosides named morroniside and loganin in rat plasma after oral administration of crude and processed Cornus officinals. Materials and Methods: A rapid, selective and specific high-performance liquid chromatography/electrospray ionization tandem mass spectrometry with multiple reactions monitoring mode was developed to simultaneously investigate the pharmacokinetic profiles of morroniside and loganin in rat plasma after oral administration of crude C. officinals and its jiuzhipin. Results: The morroniside and loganin in crude and processed C. officinals could be simultaneously determined within 7.4 min. Linear calibration curves were obtained over the concentration ranges of 45.45-4800 ng/mL for all the analytes. The intra-and inter-day precisions relative standard deviation was lesser than 2.84% and 4.12%, respectively. Conclusion: The pharmacokinetic parameters of two iridoid glucosides were also compared systematically between crude and processed C. officinals. This paper provides the theoretical proofs for further explaining the processing mechanism of Traditional Chinese Medicines. PMID:24914290

  10. Crotalionosides A-C, three new megastigmane glucosides, two new pterocarpan glucosides and a chalcone C-glucoside from the whole plants of Crotalaria zanzibarica.

    PubMed

    Shitamoto, Junko; Matsunami, Katsuyoshi; Otsuka, Hideaki; Shinzato, Takakazu; Takeda, Yoshio

    2010-08-01

    From a 1-BuOH-soluble fraction of the MeOH extract of the leaves of Crotalaria zanzibarica collected in the Okinawa Islands, three new megastigmane glucosides, named crotalionosides A-C, two new pterocarpan glucosides and a chalcone C-glucoside were isolated together with two known flavonoid glycosides and one known megastigmane glucoside. The structures of the new compounds were elucidated by a combination of spectroscopic analyses. The absolute configurations of allenic megastigmane glucosides were determined by application of the modified Mosher's method. Those of the allenic moieties were determined by interpretation of the circular dichroism (CD) spectra of the reduction products derived from citrosides A and B. The aglycones of pterocarpan glucosides were found to be melilotocarpan B and the absolute structure of the chalcone C-glucoside was determined by comparison of the CD spectral behavior with the reported values. PMID:20686254

  11. Enzymatic synthesis of glucoside derivatives of validamine and valienamine.

    PubMed

    Furumoto, T; Kameda, Y; Matsui, K

    1992-07-01

    alpha- And beta-glucoside derivatives of validamine and valienamine were prepared by enzymatic transglucosidation using alpha- and beta-glucosidase of Rhodotorula lactosa. The structures of these derivatives have been elucidated by 13C- and 1H-nuclear magnetic resonance spectral analysis. Thus, 7-alpha-glucoside, 7-alpha-isomaltoside, and 4-alpha-glucoside of validamine and 7-alpha-glucoside, 7-alpha-isomaltoside, 4-alpha-glucoside, and 4-alpha-isomaltoside of valienamine were obtained from maltose and validamine or valienamine using alpha-glucosidase. 7-beta-glucoside, 2-beta-glucoside, and 4-beta-glucoside of validamine or valienamine were obtained from cellobiose and validamine or valienamine using beta-glucosidase. These derivatives were tested for alpha-glucosidase inhibitory activity on rat small intestinal glycosidases. PMID:1394706

  12. Properties of glucoside 3-dehydrogenase and its potential applications

    Microsoft Academic Search

    Li-Qun Jin; Yu-Guo Zheng

    Glucoside 3-dehydrogenase, one of the glucose redoxidases, is perhaps known for the vital role it plays in converting a series of sugars to their corresponding 3-ketoglucosides. Glucoside 3- dehydrogenase has attracted considerable attention in recent years due to broad substrate specificity and excellent regioselectivity. Glucoside 3-dehydrogenase is a FAD-enzyme, which is capable of oxidizing glucosides and galactosides to their corresponding

  13. Monoterpene and pregnane glucosides from Solenostemma argel.

    PubMed

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

    2000-04-01

    From the aerial parts of Solenostemma argel, two monoterpene glucosides have been isolated and identified as 6,7-dihydroxy-dihydrolinalool 3-O-beta-glucopyranoside and 6,7-dihydroxy-dihydrolinalool 7-O-beta-glucopyranoside. A pregnane glucoside was also isolated and assigned as pregn-5-ene-3,14-beta-dihydroxy-7,20-dione 3-O-beta-glucopyranoside together with the known compounds benzyl alcohol O-beta-apiofuranosyl-(1-->6)-beta-glucopyranoside, 2-phenylethyl O-alpha-arabinopyranosyl-(1-->6)-beta-glucopyranoside, astragalin and kaempferol-3-O-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside. PMID:10820807

  14. Sesquiterpene lactone glucosides from Sonchus asper.

    PubMed

    Helal, A M; Nakamura, N; El-Askary, H; Hattori, M

    2000-02-01

    From the methanolic extract of the roots of Sonchus asper, two new sesquiterpene glucosides, together with two known sesquiterpene glucosides and a known aglycone were isolated. Structures were identified as 11beta,13-dihydrourospermal A, 15-O-beta-D-glucopyranosyl-11beta,13-dihydrourospermal A, 15-O-beta-D-glucopyranosylurospermal A, 15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurosperm al A and 14-O-methylacetal-15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-+ ++glucopyranosylurospermal A, by spectroscopic means. PMID:10731026

  15. Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans

    Microsoft Academic Search

    M. Olthof; P. C. H. Hollman; T. B. Vree; M. B. Katan

    2000-01-01

    The flavonoid quercetin is an antioxidant which occurs in foods mainly as glycosides. The sugar moiety in quercetin glycosides affects their bioavailability in humans. Quercetin-3-rutinoside is an important form of quercetin in foods, but its bioavailability in humans is only 20?f that of quercetin-4'-glucoside. Quercetin-3-rutinoside can be transformed into quercetin-3-glucoside by splitting off a rhamnose molecule. We studied whether this

  16. Acylated iridoids from the roots of Valeriana officinalis var. latifolia.

    PubMed

    Han, Zhu-zhen; Yan, Zhao-hui; Liu, Qing-xin; Hu, Xian-qing; Ye, Ji; Li, Hui-liang; Zhang, Wei-dong

    2012-10-01

    Phytochemical investigation of the roots of Valeriana officinalis var. latifolia resulted in the isolation and characterization of six new acylated iridoids, (5S,7S,8S,9S)-7-hydroxy-8-isovaleroyloxy-??,¹¹-dihyronepetalactone (1), (5S,7S,8S,9S)-7-hydroxy-10-isovaleroyloxy-??,¹¹-dihyronepetalactone (2), (5S,8S,9S)-10-isovaleroyloxy-??,¹¹-dihyronepetalactone (3), (5S,6S,8S,9R)-6-isovaleroyloxy-??,¹¹-1,3-diol (4), (5S,6S,8S,9R)-1,3-isovaleroxy-?4,11-1,3-diol (5), and (5S,6S,8S,9R)-3-isovaleroxy-6-isovaleroyloxy-??,¹¹-1,3-diol (6). Their structures were determined mainly by 1D and 2D?NMR spectroscopic techniques. We also report herein for the first time the single crystal X-ray structure of compound 1. In addition, the cytotoxic activities of compounds 1-6 were evaluated against A549 (human lung adenocarcinoma), HCT116 (human colon carcinoma), SK-BR-3 (human breast carcinoma), and HepG2 (human hepatoma) cell lines. Compound 6 showed weak cell growth inhibition of A549, HCT116, SK-BR-3, and HepG2 cells. PMID:22872588

  17. 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

  18. New iridoids from the medicinal plant Barleria prionitis with potent activity against respiratory syncytial virus.

    PubMed

    Chen, J L; Blanc, P; Stoddart, C A; Bogan, M; Rozhon, E J; Parkinson, N; Ye, Z; Cooper, R; Balick, M; Nanakorn, W; Kernan, M R

    1998-10-01

    Two new iridoid glycosides (1 and 2), together with the known compounds barlerin (3) and verbascoside (4), were isolated from Barleria prionitis. The new iridoid glycosides were determined to be 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (1) and its cis isomer (2) by using spectroscopic, especially 2D NMR, data. A 3:1 mixture of 1 and 2 was shown to have potent in vitro activity against respiratory syncytial virus (EC50 2.46 microgram/mL, IC50 42.2 microgram/mL). PMID:9784173

  19. Two new benzylbenzoate glucosides from Curculigo orchioides.

    PubMed

    Valls, Josep; Richard, Tristan; Larronde, Fabienne; Leblais, Véronique; Muller, Bernard; Delaunay, Jean-Claude; Monti, Jean-Pierre; Ramawat, K G; Mérillon, Jean-Michel

    2006-09-01

    An extract from in vitro cultures of Curculigo orchioides grown as bulbils in shake flasks, afforded two new glucosides of substituted benzylbenzoate - curculigoside C (3) and curculigoside D (4) - together with two known compounds - curculigoside A (1) and curculigoside B (2). Their structures were elucidated on the basis of spectral evidence, in particular by using 2D NMR methods. Their vasoactive properties were assessed in isolated rat aortic rings. PMID:16814485

  20. Metabolically Active Glucosides in Oleaceae Seeds

    PubMed Central

    Sondheimer, E.; Blank, G. E.; Galson, Eva C.; Sheets, F. M.

    1970-01-01

    The seeds of six woody species of Oleaceae representing three genera, contain high concentrations of water-soluble glucosides, with major absorption maxima below 240 nanometers. In Fraxinus americana seeds three of these compounds, designated GL-3, GL-5, and GL-6, account for almost 10% of the dry weight. They are found in the endosperm and embryo but not in the pericarp. While the level of GL-5 is not particularly influenced by the physiological state of the embryo, that of GL-3 and GL-6 decreases as a result of germination and growth during a 10-day period. As the concentrations of GL-3 and GL-6 decrease, new ultraviolet-absorbing compounds are formed. The changes in the concentration of the ultraviolet-absorbing glucosides during cold temperature after-ripening, prior to germination, are small. When germination of dormant embryos is induced with gibberellic acid, the concentrations of GL-3 and GL-6 decrease in a manner similar to that observed with nondormant embryos. In the presence of abscisic acid no losses of GL-3 and GL-6 were observed. It is suggested that GL-3 and GL-6 fulfill some definite functions in the germination and growth of F. americana embryos, and that gibberellic acid and abscisic acid can exert a regulatory effect on the metabolism of these glucosides. Images PMID:16657368

  1. A new iridoid from Guettarda grazielae M.R.V. Barbosa (Rubiaceae)

    Microsoft Academic Search

    Fabyanne S. Moura; Gerson S. Lima; Mario R. Meneghetti; Rosangela P. Lyra Lemos; Lucia M. Conserva

    2011-01-01

    Chromatographic fractionation of the chloroform extracts from the stem bark and stems of Guettarda grazielae resulted in the isolation of a new iridoid (guettardodiol, 1) and the secoiridoid sarracenin (2), described for the first time in this genus. The structural elucidation of these compounds was based on spectroscopic analyses (IR, MS as well as 1-D and 2-D NMR experiments).

  2. Characterization of 10-Hydroxygeraniol Dehydrogenase from Catharanthus roseus Reveals Cascaded Enzymatic Activity in Iridoid Biosynthesis

    PubMed Central

    Krithika, Ramakrishnan; Srivastava, Prabhakar Lal; Rani, Bajaj; Kolet, Swati P.; Chopade, Manojkumar; Soniya, Mantri; Thulasiram, Hirekodathakallu V.

    2015-01-01

    Catharanthus roseus [L.] is a major source of the monoterpene indole alkaloids (MIAs), which are of significant interest due to their therapeutic value. These molecules are formed through an intermediate, cis-trans-nepetalactol, a cyclized product of 10-oxogeranial. One of the key enzymes involved in the biosynthesis of MIAs is an NAD(P)+ dependent oxidoreductase system, 10-hydroxygeraniol dehydrogenase (Cr10HGO), which catalyses the formation of 10-oxogeranial from 10-hydroxygeraniol via 10-oxogeraniol or 10-hydroxygeranial. This work describes the cloning and functional characterization of Cr10HGO from C. roseus and its role in the iridoid biosynthesis. Substrate specificity studies indicated that, Cr10HGO has good activity on substrates such as 10-hydroxygeraniol, 10-oxogeraniol or 10-hydroxygeranial over monohydroxy linear terpene derivatives. Further it was observed that incubation of 10-hydroxygeraniol with Cr10HGO and iridoid synthase (CrIDS) in the presence of NADP+ yielded a major metabolite, which was characterized as (1R, 4aS, 7S, 7aR)-nepetalactol by comparing its retention time, mass fragmentation pattern, and co-injection studies with that of the synthesized compound. These results indicate that there is concerted activity of Cr10HGO with iridoid synthase in the formation of (1R, 4aS, 7S, 7aR)-nepetalactol, an important intermediate in iridoid biosynthesis. PMID:25651761

  3. A new iridoid from Guettarda grazielae M.R.V. Barbosa (Rubiaceae).

    PubMed

    Moura, Fabyanne S; Lima, Gerson S; Meneghetti, Mario R; Lyra Lemos, Rosangela P; Conserva, Lucia M

    2011-10-01

    Chromatographic fractionation of the chloroform extracts from the stem bark and stems of Guettarda grazielae resulted in the isolation of a new iridoid (guettardodiol, 1) and the secoiridoid sarracenin (2), described for the first time in this genus. The structural elucidation of these compounds was based on spectroscopic analyses (IR, MS as well as 1-D and 2-D NMR experiments). PMID:22011220

  4. Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae).

    PubMed

    Berger, Andreas; Kostyan, Maria Katharina; Klose, Simon Immo; Gastegger, Michael; Lorbeer, Eberhard; Brecker, Lothar; Schinnerl, Johann

    2015-08-01

    During comparative analysis on Palicourea species from Costa Rica, two unusual loganin derived tryptamine-iridoid alkaloids were isolated from an accession of Palicourea crocea. Besides the already known brachycerine (2), palicroceaine (1) features a novel hexacyclic backbone. A second provenance, however, yielded strictosidinic acid (3), belonging to the more common secologanin derived tryptamine-iridoid alkaloids, such as those found in Palicourea padifolia. From this species, strictosidine (4), lyaloside (5) and its derivative (E)-O-(6')-(4?-hydroxy-3?,5?-dimethoxy)-cinnamoyl lyaloside (6) could be isolated. A herbarium specimen-based screening was performed, indicating some degree of regional differentiation in alkaloid content and biosynthetic pathways within the widespread and variable Pal. crocea. It further shows its differentiation from the related strictosidine containing Palicourea croceoides. The occurrence of loganin derived tryptamine-iridoid alkaloids in Pal. crocea, Psychotria brachyceras and Psychotria brachypoda, all putatively unrelated members of the Palicourea s.l. clade, is a noteworthy exception within the genus, otherwise largely characterized by secologanin-derived tryptamine-iridoid alkaloids. PMID:26043882

  5. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... Methyl glucoside-coconut oil ester. 573.660 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  6. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... Methyl glucoside-coconut oil ester. 172.816 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  7. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... Methyl glucoside-coconut oil ester. 573.660 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  8. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... Methyl glucoside-coconut oil ester. 172.816 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  9. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... Methyl glucoside-coconut oil ester. 573.660 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  10. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... Methyl glucoside-coconut oil ester. 172.816 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  11. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... Methyl glucoside-coconut oil ester. 178.3600 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in §...

  12. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... Methyl glucoside-coconut oil ester. 178.3600 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in §...

  13. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... Methyl glucoside-coconut oil ester. 573.660 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  14. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... Methyl glucoside-coconut oil ester. 172.816 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used...

  15. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... Methyl glucoside-coconut oil ester. 178.3600 Section...ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in §...

  16. New flavanone and chalcone glucosides from Bidens bipinnata Linn.

    PubMed

    Li, Shuai; Kuang, Hai-Xue; Okada, Yoshihito; Okuyama, Toru

    2005-02-01

    A new flavanone glucoside, bidenoside F, and a new chalcone glucoside, bidenoside G, along with the known compound iso-okanin 7-O-(4'',6''-diacetyl)-beta-D-glucopyranoside have been isolated from the aerial parts of Bidens bipinnata L. The structures were determined on the basis of spectroscopic methods. PMID:15621604

  17. Indonesian Medicinal Plants. XIV. Characterization of 3'-O-Caffeoylsweroside, a new secoiridoid glucoside, and kelampayosides A and B, two new phenolic apioglucosides, from the bark of Anthocephalus chinensis (Rubiaceae).

    PubMed

    Kitagawa, I; Wei, H; Nagao, S; Mahmud, T; Hori, K; Kobayashi, M; Uji, T; Shibuya, H

    1996-06-01

    A new secoiridoid glucoside named 3'-O-caffeoylsweroside (1), and two new phenolic apioglucosides, named kelampayoside A (4) and kelampayoside B (6), together with eleven known compounds (five iridoids and six alkaloids), were isolated from the bark of Anthocephalus chinensis (Rubiaceae), an Indonesian medicinal plant from Sumatra Island, Indonesia. The chemical structures of 1, 4 and 6 have been elucidated respectively as 3'-O-caffeoylsweroside (1), antiarol 1-O-beta-D-apiofuranosyl (1 --> 6)-beta-D-glucopyranoside (4), and antiarol 1-O-beta-D-5"-O-caffeoylapiofuransoyl (1 --> 6)-beta-D-glucopyranoside (6) on the bases of their chemical and physiochemical properties. Among fourteen constituents characterized, cadambine (13), one of the major indole alkaloid constituents of A. chinensis, was shown to exhibit moderate growth-inhibitory activity against the malarial parasite Plasmodium falciparum (a chloroquine-resistant K1 strain) cultured in human erythrocytes. PMID:8814946

  18. Hirtionosides A-C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta.

    PubMed

    Nomoto, Yuya; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2013-04-01

    From the 1-BuOH-soluble fraction of a MeOH extract of Euphorbia hirta, collected in the Okinawa islands, three new megastigmane glucoside gallates, named hirtionosides A-C, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside were isolated along with 15 known compounds. The structures of the new compounds were elucidated by detailed analysis of physical data, including one- and two-dimensional NMR spectra, and those of known compounds were determined by comparison of physico-chemical data with those reported in the literature. The absolute structures of the megastigmanes were determined by comparison of NMR data and Cotton effects in the CD spectra. The modified Mosher's method was applied to determine the absolute structure of the chiral center in 3-hydroxyoctanoic acid. The DPPH radical-scavenging properties of megastigmane glucoside gallates were assayed and, as expected, they showed moderate activity. PMID:22836810

  19. Synthesis of guaiacol-alpha-D: -glucoside and curcumin-bis-alpha-D: -glucoside by an amyloglucosidase from Rhizopus.

    PubMed

    R Vijayakumar, Giriyapura; Divakar, Soundar

    2005-09-01

    Guaiacol (2-methoxyphenol) and curcumin [1E,6E-1,7-di(4-hydroxy-3-methoxy-phenyl)-1,6-heptadiene-3,5-dione] were converted into their corresponding glucosides using glucose and an amyloglucosidase from Rhizopus. Guaiacol-alpha-D: -glucoside yields ranged from 3 to 52% with the highest at pH 7.0. Curcumin-bis-alpha-D: -glucoside yields ranged from 3 to 48% with the highest at pH 4.0 with 50% (w/w D: -glucose) of enzyme. The phenolic hydroxyl group of guaiacol and both phenolic hydroxyl groups of curcumin were glucosylated at the C1 carbon of alpha-D: -glucose indicating that the enzymatic reaction is stereospecific. Both guaiacol-alpha-D: -glucoside and curcumin-bis-alpha-D: -glucosides had antioxidant activities. PMID:16215859

  20. 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

  1. Zearalenone-16-O-glucoside: a new masked mycotoxin.

    PubMed

    Kovalsky Paris, Maria Paula; Schweiger, Wolfgang; Hametner, Christian; Stückler, Romana; Muehlbauer, Gary J; Varga, Elisabeth; Krska, Rudolf; Berthiller, Franz; Adam, Gerhard

    2014-02-01

    This paper reports the identification of a barley UDP-glucosyltransferase, HvUGT14077, which is able to convert the estrogenic Fusarium mycotoxin zearalenone into a near-equimolar mixture of the known masked mycotoxin zearalenone-14-O-?-glucoside and a new glucose conjugate, zearalenone-16-O-?-glucoside. Biocatalytical production using engineered yeast expressing the HvUGT14077 gene allowed structural elucidation of this compound. The purified zearalenone-16-O-?-glucoside was used as an analytical calibrant in zearalenone metabolization experiments. This study confirmed the formation of this new masked mycotoxin in barley seedlings as well as in wheat and Brachypodium distachyon cell suspension cultures. In barley roots, up to 18-fold higher levels of zearalenone-16-O-?-glucoside compared to the known zearalenone-14-O-?-glucoside were found. Incubation of zearalenone-16-O-?-glucoside with human fecal slurry showed that this conjugate can also be hydrolyzed rapidly by intestinal bacteria, converting the glucoside back to the parental mycotoxin. Consequently, it should be considered as an additional masked form of zearalenone with potential relevance for food safety. PMID:24386883

  2. Phaedon cochleariae and Gastrophysa viridula (Coleoptera: Chrysomelidae) produce defensive iridoid monoterpenes de novo and are able to sequester glycosidically bound terpenoid precursors

    Microsoft Academic Search

    Birte K. Feld; Jacques M. Pasteels; Wilhelm Boland

    2001-01-01

    Summary. Larvae of the chrysomelid beetles Phaedon cochleariae and Gastrophysa viridula use iridoid monoterpenes for defense. The compounds are synthesized de novo in the glandular tissue and the reservoir. However, larvae feeding on leaves impregnated with thioglycosides of early precursors of iridoid biosynthesis such as the thioglycosides of 8-hydroxygeraniol, 8 and 9, rapidly accumulate in their defensive secretion. Thioglycosides combine

  3. A New Phenolic Glucoside, Curculigoside from Rhizomes of Curculigo orchioides.

    PubMed

    Kubo, M; Namba, K; Nagamoto, N; Nagao, T; Nakanishi, J; Uno, H; Nishimura, H

    1983-01-01

    A new phenolic glucoside, named curculigoside (I), was isolated from the rhizomes of CURCULIGO ORCHIOIDES G AERTN. and its structure was elucidated as 5-hydroxy-2-O-beta-D-glucopyranosylbenzyl 2,6-dimetoxybenzoate. PMID:17405094

  4. Isobiflorin, a chromone C-glucoside from cloves ( Eugenia caryophyllata)

    Microsoft Academic Search

    Yongwen Zhang; Yuwu Chen

    1997-01-01

    The polyoxygenated chromone C-glucoside, isobiflorin (5,7-dihydroxy-2-methylchromone-8-C-?-d-glucopyranoside), and biflorin were isolated from an ethanolic extract of cloves (Eugenia caryophyllata), and characterized by chemical and spectral analysis.

  5. A New Flavone 2?Glucoside from Andrographis alata

    Microsoft Academic Search

    A. G. Damu; B. Jayaprakasam; D. Gunasekar

    1998-01-01

    A new flavone glucoside, 5,2?,6?-trihydroxy-7-methoxyflavone 2?-O-?-D-glucopyranoside has been isolated from the whole plant of Andrographis alata. The structure was elucidated on the basis of spectral and chemical evidence.

  6. 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

  7. Geniposide and its iridoid analogs exhibit antinociception by acting at the spinal GLP-1 receptors.

    PubMed

    Gong, Nian; Fan, Hui; Ma, Ai-Niu; Xiao, Qi; Wang, Yong-Xiang

    2014-09-01

    We recently discovered that the activation of the spinal glucagon-like peptide-1 receptors (GLP-1Rs) by the peptidic agonist exenatide produced antinociception in chronic pain. We suggested that the spinal GLP-1Rs are a potential target molecule for the management of chronic pain. This study evaluated the antinociceptive activities of geniposide, a presumed small molecule GLP-1R agonist. Geniposide produced concentration-dependent, complete protection against hydrogen peroxide-induced oxidative damage in PC12 and HEK293 cells expressing rat and human GLP-1Rs, but not in HEK293T cells that do not express GLP-1Rs. The orthosteric GLP-1R antagonist exendin(9-39) right-shifted the concentration-response curve of geniposide without changing the maximal protection, with identical pA2 values in both cell lines. Subcutaneous and oral geniposide dose-dependently blocked the formalin-induced tonic response but not the acute flinching response. Subcutaneous and oral geniposide had maximum inhibition of 72% and 68%, and ED50s of 13.1 and 52.7 mg/kg, respectively. Seven days of multidaily subcutaneous geniposide and exenatide injections did not induce antinociceptive tolerance. Intrathecal geniposide induced dose-dependent antinociception, which was completely prevented by spinal exendin(9-39), siRNA/GLP-1R and cyclic AMP/PKA pathway inhibitors. The geniposide iridoid analogs geniposidic acid, genipin methyl ether, 1,10-anhydrogenipin, loganin and catalpol effectively inhibited hydrogen peroxide-induced oxidative damage and formalin pain in an exendin(9-39)-reversible manner. Our results suggest that geniposide and its iridoid analogs produce antinociception during persistent pain by activating the spinal GLP-1Rs and that the iridoids represented by geniposide are orthosteric agonists of GLP-1Rs that function similarly in humans and rats and presumably act at the same binding site as exendin(9-39). PMID:24747181

  8. 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

  9. A new unusual iridoid with inhibition of activator protein-1 (AP-1) from the leaves of Morinda citrifolia L.

    PubMed

    Sang, S; He, K; Liu, G; Zhu, N; Cheng, X; Wang, M; Zheng, Q; Dong, Z; Ghai, G; Rosen, R T; Ho, C T

    2001-05-01

    [structure in text] From the leaves of Morinda citrifolia, a new unusual iridoid, named citrifolinoside (1), showing significant inhibition of UVB-induced Activator Protein-1 (AP-1) activity in cell cultures, has been isolated. Its structure was elucidated on the basis of detailed high-field 1D and 2D spectral analysis. PMID:11348221

  10. Application of Cornelian Cherry Iridoid-Polyphenolic Fraction and Loganic Acid to Reduce Intraocular Pressure

    PubMed Central

    Szumny, Dorota; Soza?ski, Tomasz; Kucharska, Alicja Z.; Dziewiszek, Wojciech; Piórecki, Narcyz; Magdalan, Jan; Chlebda-Sieragowska, Ewa; Kupczynski, Robert; Szel?g, Adam; Szumny, Antoni

    2015-01-01

    One of the most common diseases of old age in modern societies is glaucoma. It is strongly connected with increased intraocular pressure (IOP) and could permanently damage vision in the affected eye. As there are only a limited number of chemical compounds that can decrease IOP as well as blood flow in eye vessels, the up-to-date investigation of new molecules is important. The chemical composition of the dried Cornelian cherry (Cornus mas L.) polar, iridoid-polyphenol-rich fraction was investigated. Loganic acid (50%) and pelargonidin-3-galactoside (7%) were found as the main components. Among the other constituents, iridoid compound cornuside and the anthocyans cyanidin 3-O-galactoside, cyanidin 3-O-robinobioside, and pelargonidin 3-O-robinobioside were quantified in the fraction. In an animal model (New Zealand rabbits), the influence of loganic acid and the polyphenolic fraction isolated from Cornelian cherry fruit was investigated. We found a strong IOP-hypotensive effect for a 0.7% solution of loganic acid, which could be compared with the widely ophthalmologically used timolol. About a 25% decrease in IOP was observed within the first 3 hours of use.

  11. Naphthohydroquinone glucosides of Drosera rotundifolia and D. intermedia from in vitro cultures

    Microsoft Academic Search

    Jaromir Budzianowski

    1996-01-01

    Rossoliside (7-methylhydrojuglone 4-O-glucoside) was isolated from Drosera rotundifolia, together with hydroplumbagin 4-O-glucoside, from D. intermedia, both of which were produced by in vitro micropropagation. Hydroplumbagin glucoside released the corresponding 1,4-naphthoquinone (plumbagin) more rapidly than rossoliside (7-methyljuglone). These glucosides can be detected in plant extracts by reversed-phase TLC and appearance of the corresponding free quinones after treatment with ?-glucosidase.

  12. Growth inhibitory activity of cucurbitacin glucosides isolated from Citrullus colocynthis on human breast cancer cells

    Microsoft Academic Search

    Tehila Tannin-Spitz; Shlomo Grossman; Sara Dovrat; Hugo E. Gottlieb; Margalit Bergman

    2007-01-01

    Our aim was to study the effects of cucurbitacin glucosides extracted from Citrullus colocynthis leaves on human breast cancer cell growth. Leaves were extracted, resulting in the identification of cucurbitacin B\\/E glucosides. The cucurbitacin glucoside combination (1:1) inhibited growth of ER+ MCF-7 and ER? MDA-MB-231 human breast cancer cell lines. Cell-cycle analysis showed that treatment with isolated cucurbitacin glucoside combination

  13. Interaction of quercetin glucosides with the intestinal sodium\\/glucose co-transporter (SGLT-1)

    Microsoft Academic Search

    Peter Ader; Markus Blöck; Silke Pietzsch; Siegfried Wolffram

    2001-01-01

    Recently it has been postulated that flavonoid glucosides may be absorbed by the small intestine via the SGLT-1. Therefore, we applied an in vitro mucosal uptake method to investigate mucosal uptake of the non-metabolisable glucose analogue methyl-?-d-glucopyranoside (MDG) as influenced by quercetin-3-glucoside (isoquercitrin) and quercetin-4? -glucoside (spiraeosid). We found that both glucosides significantly inhibited SGLT-1-mediated MDG uptake whereas the aglycon

  14. Importance of phenolic glucosides in host selection of shoot galling sawfly, Euura amerinae , on Salix pentandra

    Microsoft Academic Search

    Jari Kolehmainen; Heikki Roininen; Riitta Julkunen-Tiitto; Jorma Tahvanainen

    1994-01-01

    The effects of phenolic glucosides on the oviposition behavior ofEuura amerinae L. (Hymenoptera: Tenthredinidae) were tested in multiple oviposition experiments using different shoot length categories ofSalix pentandra L. (with different amounts of phenolic glucosides) and in experiments with pure phenolic glucosides (salidroside, arbutin, salicin, 90% salicortin, 90% 2?-O-acetylsalicortin) or composite total fractions of phenolic glucosides from three willow species (S.

  15. Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium

    Microsoft Academic Search

    Hideaki Otsuka; Eiji Hirata; Takakazu Shinzato; Yoshio Takeda

    2003-01-01

    From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9-O-?-d-glucopyranosides of (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside (3) and actinidioionoside (4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E (5) and O (6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides,

  16. Characterization of diterpenoid glucosides in roasted puer coffee beans.

    PubMed

    Shu, Yi; Liu, Jie-Qing; Peng, Xing-Rong; Wan, Luo-Sheng; Zhou, Lin; Zhang, Tao; Qiu, Ming-Hua

    2014-03-26

    Five new diterpenoid glucosides, named mascaroside I (1), mascaroside II (2), paniculoside VI (3), cofaryloside I (4), and villanovane I (5), along with seven known ent-kaurane diterpenoid glucosides (6-12) were isolated from acetone extracts of the roasted coffee beans of Coffea arabica var. yunnanensis. Their structures were established by extensive spectroscopic analysis including 1D and 2D NMR (HSQC, HMBC, COSY, and ROESY) and by comparison with published data. Cytotoxicities evaluation of the isolates showed that they were inactive against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cells. PMID:24605833

  17. Metabolism of conjugated sterols in eggplant. Part 2. Phospholipid : steryl glucoside acyltransferase

    Microsoft Academic Search

    Anna Potocka; Jan Zimowski

    A membrane-bound phospholipid : steryl glucoside acyltransferase from Solanum melongena leaves was partially purified and its specificity and molecular as well as kinetic properties were defined. Among the steryl glycosides tested (e.g. typical plant steryl glucosides, steryl galacto - sides and cholesteryl xyloside) the highest activity was found with cholesteryl glucoside, but some structurally related compounds such as sito- and

  18. Heteroaryl- O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1

    Microsoft Academic Search

    Xiaoyan Zhang; Maud Urbanski; Mona Patel; Roxanne E. Zeck; Geoffrey G. Cox; Haiyan Bian; Bruce R. Conway; Mary Pat Beavers; Philip J. Rybczynski; Keith T. Demarest

    2005-01-01

    A series of benzo-fused heteroaryl-O-glucosides was synthesized and evaluated in SGLT1 and 2 cell-based functional assays. Indole-O-glucoside 10a and benzimidazole-O-glucoside 18 exhibited potent in vitro SGLT2 inhibitory activity.

  19. Effect of the temperature and the exclusion of UVB radiation on the phenolics and iridoids in Menyanthes trifoliata L. leaves in the subarctic.

    PubMed

    Martz, Françoise; Turunen, Minna; Julkunen-Tiitto, Riitta; Lakkala, Kaisa; Sutinen, Marja-Liisa

    2009-12-01

    The long-term effects of UVB exclusion and temperature on the methanol extractable (ME) phenolics (flavonoids, phenolic acids) and iridoids of Menyanthes trifoliata L. (Mt) leaves were studied in northern Finland (68 degrees N) using wooden frames covered with filters for UVB exclusion (polyester filter), control (cellulose acetate filter) and ambient (no filter) conditions. Analysis of ambient plots showed no effect of the daily mean temperature (2sigma = 1.58 degrees C) on the leaf ME compound content and composition, but minimum temperatures decreased the flavonol content. UVB exclusion did not affect the total ME compound content but significantly decreased the proportion of flavonols concomitantly with an increase in iridoids. Due to its high iridoid content, Mt appears as an interesting model plant for studying the iridoid biosynthesis and its regulation under stress conditions. PMID:19615800

  20. Enzymatic synthesis of [3'-O-methyl-(3)H]malvidin-3-glucoside from petunidin-3-glucoside.

    PubMed

    Zimman, Alejandro; Waterhouse, Andrew L

    2002-04-10

    Malvidin-3-glucoside has been labeled by enzymatic synthesis in a single-step experiment. Catechol-O-methyl transferase catalyzed the B-ring methylation of petunidin-3-glucoside, and S-Adenosyl-L-[methyl-(3)H] methionine was the methyl donor. Solid phase extraction and preparative high-performance liquid chromatography were necessary to separate [3'-O-methyl-(3)H]malvidin-3-glucoside from an isomer and the starting material. The specific activity was 2.2 Ci mmol(-1), and the yield of incorporation was 1.1%. A possible application of the labeled material is the study of anthocyanin reactions in complex mixtures such as red wine where products are difficult to isolate and analyze. PMID:11929308

  1. Biosynthesis of the Nitrile Glucosides Rhodiocyanoside A and D and the Cyanogenic Glucosides Lotaustralin and Linamarin in Lotus japonicus1

    PubMed Central

    Forslund, Karin; Morant, Marc; Jørgensen, Bodil; Olsen, Carl Erik; Asamizu, Erika; Sato, Shusei; Tabata, Satoshi; Bak, Søren

    2004-01-01

    Lotus japonicus was shown to contain the two nitrile glucosides rhodiocyanoside A and rhodiocyanoside D as well as the cyanogenic glucosides linamarin and lotaustralin. The content of cyanogenic and nitrile glucosides in L. japonicus depends on plant developmental stage and tissue. The cyanide potential is highest in young seedlings and in apical leaves of mature plants. Roots and seeds are acyanogenic. Biosynthetic studies using radioisotopes demonstrated that lotaustralin, rhodiocyanoside A, and rhodiocyanoside D are derived from the amino acid l-Ile, whereas linamarin is derived from Val. In silico homology searches identified two cytochromes P450 designated CYP79D3 and CYP79D4 in L. japonicus. The two cytochromes P450 are 94% identical at the amino acid level and both catalyze the conversion of Val and Ile to the corresponding aldoximes in biosynthesis of cyanogenic glucosides and nitrile glucosides in L. japonicus. CYP79D3 and CYP79D4 are differentially expressed. CYP79D3 is exclusively expressed in aerial parts and CYP79D4 in roots. Recombinantly expressed CYP79D3 and CYP79D4 in yeast cells showed higher catalytic efficiency with l-Ile as substrate than with l-Val, in agreement with lotaustralin and rhodiocyanoside A and D being the major cyanogenic and nitrile glucosides in L. japonicus. Ectopic expression of CYP79D2 from cassava (Manihot esculenta Crantz.) in L. japonicus resulted in a 5- to 20-fold increase of linamarin content, whereas the relative amounts of lotaustralin and rhodiocyanoside A/D were unaltered. PMID:15122013

  2. Ring B aromatic norpimarane glucoside from a Xylaria sp.

    PubMed

    Isaka, Masahiko; Yangchum, Arunrat; Auncharoen, Patchanee; Srichomthong, Kitlada; Srikitikulchai, Prasert

    2011-02-25

    A novel 20-norpimarane glucoside, xylopimarane (1), together with the known sphaeropsidin C (2) and clonostachydiol (3), was isolated from the fungus Xylaria sp. BCC 4297. Compound 1 exhibited cytotoxicity to cancer cell lines KB, MCF-7, and NCI-H187 with respective IC(50) values of 1.0, 13, and 65 ?M. PMID:21226484

  3. A new flavone 2'-glucoside from Andrographis alata.

    PubMed

    Damu, A G; Jayaprakasam, B; Gunasekar, D

    1998-01-01

    A new flavone glucoside, 5,2',6'-trihydroxy-7-methoxyflavone 2'-O-beta-D-glucopyranoside has been isolated from the whole plant of Andrographis alata. The structure was elucidated on the basis of spectral and chemical evidence. PMID:11261214

  4. Portuloside A, a monoterpene glucoside, from Portulaca oleracea

    Microsoft Academic Search

    Naomi Sakai; Kyouko Inada; Michi Okamoto; Yoshikazu Shizuri; Yoshiyasu Fukuyama

    1996-01-01

    From the methanol extract of Portulaca oleracea, a new monoterpene glucoside, portuloside A, has been isolated. The structure of portuloside A was established by spectroscopic methods and then confirmed to be (3S)-3-(3,7-dimethylocta-1,7-dien-6-onyl)-?-d-glucopyranoside by synthesis from linalool.

  5. Isolation and purification of closely related citrus limonoid glucosides by flash chromatography.

    PubMed

    Raman, Girija; Cho, Minhee; Brodbelt, Jennifer S; Patil, Bhimanagouda S

    2005-01-01

    Several citrus limonoid glycosides have proved to be particularly difficult to purify using conventional techniques. A reversed-phase flash chromatographic technique has been developed for the separation and isolation of the closely related limonoid glucosides, nomilin 17-beta-D-glucopyranoside and nomilinic acid 17-beta-D-glucopyranoside, with confirmation of their identities by electrospray ionisation mass spectrometry. Furthermore, the semi-purification of the mixture of glucosides enriched with flavanone glucosides such as naringin, narirutin and other limonoid glucosides was obtained. The closely eluting glucosides were successfully separated to achieve a good yield and purity of 93%. PMID:15997847

  6. Antibacterial and Antiproliferative Activities of Plumericin, an Iridoid Isolated from Momordica charantia Vine.

    PubMed

    Saengsai, Jutamas; Kongtunjanphuk, Sumonthip; Yoswatthana, Nuttawan; Kummalue, Tanawan; Jiratchariyakul, Weena

    2015-01-01

    Plumericin, an iridoid lactone, was isolated with relatively high yield from Momordica charantia vine using the supercritical fluid extraction (SFE) and the separation box (Sepbox) comprising dual combination of high-performance liquid chromatography and solid phase extraction. This compound showed antibacterial activity against Enterococcus faecalis and Bacillus subtilis with minimum inhibitory concentration (MIC) values better than cloxacillin. Plumericin potently inhibited proliferation of two leukemic cancer cell lines: they were acute and chronic leukemic cancer cell lines, NB4 and K562, with the effective doses (ED50) of 4.35 ± 0.21 and 5.58 ± 0.35??g/mL, respectively. In addition, the mechanism of growth inhibition in both cell lines was induced by apoptosis, together with G2/M arrest in K562 cells. PMID:25945113

  7. Antibacterial and Antiproliferative Activities of Plumericin, an Iridoid Isolated from Momordica charantia Vine

    PubMed Central

    Saengsai, Jutamas; Kongtunjanphuk, Sumonthip; Yoswatthana, Nuttawan; Kummalue, Tanawan

    2015-01-01

    Plumericin, an iridoid lactone, was isolated with relatively high yield from Momordica charantia vine using the supercritical fluid extraction (SFE) and the separation box (Sepbox) comprising dual combination of high-performance liquid chromatography and solid phase extraction. This compound showed antibacterial activity against Enterococcus faecalis and Bacillus subtilis with minimum inhibitory concentration (MIC) values better than cloxacillin. Plumericin potently inhibited proliferation of two leukemic cancer cell lines: they were acute and chronic leukemic cancer cell lines, NB4 and K562, with the effective doses (ED50) of 4.35 ± 0.21 and 5.58 ± 0.35??g/mL, respectively. In addition, the mechanism of growth inhibition in both cell lines was induced by apoptosis, together with G2/M arrest in K562 cells. PMID:25945113

  8. New anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth.

    PubMed

    Suzuki, Mitsuko; Tung, Nguyen Huu; Kwofie, Kofi D; Adegle, Richard; Amoa-Bosompem, Michael; Sakyiamah, Maxwell; Ayertey, Frederick; Owusu, Kofi Baffour-Awuah; Tuffour, Isaac; Atchoglo, Philip; Frempong, Kwadwo Kyereme; Anyan, William K; Uto, Takuhiro; Morinaga, Osamu; Yamashita, Taizo; Aboagye, Frederic; Appiah, Alfred Ampomah; Appiah-Opong, Regina; Nyarko, Alexander K; Yamaoka, Shoji; Yamaguchi, Yasuchika; Edoh, Dominic; Koram, Kwadwo; Ohta, Nobuo; Boakye, Daniel A; Ayi, Irene; Shoyama, Yukihiro

    2015-08-01

    Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by (1)H and (13)C NMR including HMQC, HMBC, H-H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27?M. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure-activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT. PMID:26048790

  9. Cyanidin 3Glucoside and Peonidin 3Glucoside Inhibit Tumor Cell Growth and Induce Apoptosis In Vitro and Suppress Tumor Growth In Vivo

    Microsoft Academic Search

    Pei-Ni Chen; Shu-Chen Chu; Hui-Ling Chiou; Chui-Liang Chiang; Shun-Fa Yang; Yih-Shou Hsieh

    2005-01-01

    Dietary polyphenols, including anthocyanins, are suggested to be involved in the protective effects of fruits and vegetables against cancer. However, anticancer effects of peonidin 3-glucoside have not been clearly demonstrated, with only limited studies being available concerning the in- hibitory effect of cyanidin 3-glucoside for tumor cell growth. Therefore, in this study, we have isolated and identified the two bioactive

  10. Supinaionosides A and B: megastigmane glucosides and supinanitrilosides A-F: hydroxynitrile glucosides from the whole plants of Euphorbia supina RAFINESQUE.

    PubMed

    Cai, Wen-Hu; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2009-08-01

    From whole plants of Euphorbia supina, two new megastigmane glucosides, named supinaionosides A and B (1, 2), six new hydroxynitrile glucosides, named supinanitrilosides A-F (3-8), and six known compounds were isolated. The structures of the new compounds were elucidated on the basis of spectroscopic and chemical evidence. PMID:19652410

  11. A New Benzofuran Glucoside from Ficus Tikoua Bur

    PubMed Central

    Wei, Shao-Peng; Luan, Jie-Yu; Lu, Li-Na; Wu, Wen-Jun; Ji, Zhi-Qin

    2011-01-01

    From the water-soluble portion of the methanol extract of stems of Ficus tikoua Bur., a new benzofuran glucoside, named 6-carboxyethyl-5-hydroxybenzofuran 5-O-?-d-glucopyranoside (1), together with one known benzofuran glucoside (2) were isolated. Their structures were elucidated by 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy and HRMS techniques. The antioxidant activities of the isolated compounds were assayed based on the scavenging activities of DPPH free radical. Compounds 1 and 2 exhibited moderate antioxidant activities, and the IC50 values were 242.8 ?g·mL?1 and 324.9 ?g·mL?1, respectively. PMID:21954336

  12. Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium.

    PubMed

    Otsuka, Hideaki; Hirata, Eiji; Shinzato, Takakazu; Takeda, Yoshio

    2003-03-01

    From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9-O-beta-D-glucopyranosides of (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside (3) and actinidioionoside (4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E (5) and O (6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides, and the latter is closely related to 1 and actinidioionoside (4). However, the absolute configurations of the 9-position remained to be determined. They were analyzed to be R by means of a modified Mosher's method. Alangionoside E (5) is identical with corchoionoside A in all aspects. The name of corchoionoside A must be retained thereafter. PMID:12620329

  13. Interaction between Cyanidin 3-glucoside and Cu(II) ions

    Microsoft Academic Search

    Bogdan Smyk; Barbara Pliszka; Regina Drabent

    2008-01-01

    The interaction between cyanidin 3-glucoside (Cy 3-glc) and Cu(II) in a binary solvent (methanol–water, 1:1, (v\\/v)) and in a phosphate buffer was studied. It is demonstrated that Cy 3-glc and Cu(II) ions form a complex that is manifested by appearance of a new absorption band. In the complex, the reduction of Cu(II)–Cu(I) and oxidation of Cy 3-glc takes place. The

  14. Antioxidant properties of anthocyanidins, anthocyanidin-3-glucosides and respective portisins

    Microsoft Academic Search

    Joana Azevedo; Iva Fernandes; Ana Faria; Joana Oliveira; Ana Fernandes; Victor de Freitas; Nuno Mateus

    2010-01-01

    The study of the antioxidants properties of three classes of pigments, namely anthocyanidins (cyanidin-Cy, delphinidin-Dp and malvidin-Mv), anthocyanidin-3-glucosides (Cy-3-gluc, Dp-3-gluc and Mv-3-gluc), and portisins (Cy-pt, Dp-pt and Mv-pt) was carried out. The aim was to evaluate the relationship between the structure antioxidant properties of individual anthocyanins and respective derivative pigments. The ability of these compounds to inhibit lipid peroxidation in

  15. Prenylated xanthone glucosides from Ural's lichen Umbilicaria proboscidea.

    PubMed

    Rezanka, Tomás; Jáchymová, Jitka; Dembitsky, Valery M

    2003-02-01

    Two new compounds isolated from an extract of a Central Asian lichen [Umbilicaria proboscidea (L.) Schrader=Syn.: Gyrophora proboscidea (L.) Ach.] are glucosides with mono- and di-prenylated xanthones as the aglycones and a saccharide moiety from two glucoses linked at C-7. The structures were elucidated on the basis of extensive spectroscopic analysis (1D and 2D NMR, MS, IR and UV) and by hydrolysis. PMID:12560034

  16. Prenylated xanthone glucosides from Ural's lichen Umbilicaria proboscidea

    Microsoft Academic Search

    Tomáš ?ezanka; Jitka Jáchymová; Valery M. Dembitsky

    2003-01-01

    Two new compounds isolated from an extract of a Central Asian lichen [Umbilicaria proboscidea (L.) Schrader=Syn.: Gyrophora proboscidea (L.) Ach.] are glucosides with mono- and di-prenylated xanthones as the aglycones and a saccharide moiety from two glucoses linked at C-7. The structures were elucidated on the basis of extensive spectroscopic analysis (1D and 2D NMR, MS, IR and UV) and

  17. 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

  18. 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

  19. Beetles do it differently: two stereodivergent cyclisation modes in iridoid-producing leaf-beetle larvae.

    PubMed

    Kunert, Maritta; Rahfeld, Peter; Shaker, Kamel H; Schneider, Bernd; David, Anja; Dettner, Konrad; Pasteels, Jacques M; Boland, Wilhelm

    2013-02-11

    Larvae of the Chrysomelina species Phaedon cochleariae, Hydrothassa marginella, Phratora vulgatissima, Gastrophysa viridula, Gastrophysa atrocyanea, Gastrophysa cyanea and Gastrophysa polygoni produce the iridoid chrysomelidial (1) to defend themselves against predators. Feeding experiments with a deuterated precursor ([(2)H(5)]8-hydroxygeraniol 9) and in vitro isotope exchange experiments with defensive secretion in (2)H(2)O revealed differences in the cyclisation of the ultimate precursor 8-oxogeranial (8) to 1, between members of the genus Gastrophysa and all other species. In P. cochleariae, H. marginella and P. vulgatissima 1 is most likely produced by a Rauhut-Currier-type cyclisation via a "transoid dienamine", with loss of a single deuterium atom from C(4) of the precursor. In contrast, members of the genus Gastrophysa cyclise 8 via a "cisoid dienamine" intermediate, with exchange of all three deuterium atoms from the methyl group at C(3). To study whether the different cyclisation modes influence the stereochemistry of 1, the absolute configuration of 1 of the larvae was determined by GC-MS on a chiral column. In accordance with literature (J. Meinwald, T. H. Jones, J. Am. Chem. Soc. 1978, 100, 1883 and N. Shimizu, R. Yakumaru, T. Sakata, S. Shimano, Y. Kuwahara, J. Chem. Ecol. 2012, 38, 29), we found (5S,8S)-chrysomelidial (1) in H. marginella and P. vulgatissima, but P. cochleariae and all investigated members of the genus Gastrophysa synthesise (5R,8R)-chrysomelidial (1). PMID:23341265

  20. Iridoid glycoside variation in the invasive plant Dalmatian toadflax, Linaria dalmatica (Plantaginaceae), and sequestration by the biological control agent, Calophasia lunula.

    PubMed

    Jamieson, Mary A; Bowers, M Deane

    2010-01-01

    Invasive plant species can have significant ecological and economic impacts. Although numerous hypotheses highlight the importance of the chemical defenses of invasive plant species, the chemical ecology of many invasive plants has not yet been investigated. In this study, we provide the first quantitative investigation of variation in iridoid glycoside concentrations of the invasive plant Dalmatian toadflax (Linaria dalmatica). We examined variation in chemical defenses at three levels: (1) variation within and among populations; (2) variation due to phenology and/or seasonal differences; and (3) variation among plant parts (leaves, flowers, and stems). Further, we examined two biological control agents introduced to control L. dalmatica for the ability to sequester iridoid glycosides from this invasive plant. Results indicate that L. dalmatica plants can contain high concentrations of iridoid glycosides (up to 17.4% dry weight of leaves; mean = 6.28?±?0.5 SE). We found significant variation in iridoid glycoside concentrations both within and among plant populations, over the course of the growing season, and among plant parts. We also found that one biological control agent, Calophasia lunula (Lepidoptera: Noctuidae), was capable of sequestering antirrhinoside, an iridoid glycoside found in L. dalmatica, at levels ranging from 2.7 to 7.5% dry weight. A second biological control agent, Mecinus janthinus (Coleoptera: Curculionidae), a stem-mining weevil, did not sequester iridoid glycosides. The demonstrated variation in L. dalmatica chemical defenses may have implications for understanding variation in the degree of invasiveness of different populations as well as variation in the efficacy of biological control efforts. PMID:20077129

  1. Acylated cyanidin 3-sambubioside-5-glucosides in Matthiola incana

    Microsoft Academic Search

    Norio Saito; Fumi Tatsuzawa; Akiko Nishiyama; Masato Yokoi; Atsushi Shigihara; Toshio Honda

    1995-01-01

    Four acylated cyanidin 3-sambubioside-5-glucosides were isolated from purple-violet flowers of Matthiola incana and their structures were determined by chemical and spectroscopic methods. Three acylated anthocyanins were cyanidin 3-O-(6-O-acyl-2-O-(2-O-sinapyl-?-d-glucopyranosides)-5-O-(6-O-malonyl-?-d-glucopyranosides), in which the acyl group is p-coumaryl, caffeyl or ferulyl, respectively. The remaining pigment is free from malonic acid and was identified as cyanidin 3-O-(6-O-trans-ferulyl-2-O-(2-O-trans-sinapyl-?-d-xylopyranosyl)-?-d-glucopyranoside)-5-O-(?-d- glucopyranoside). Analysis of the anthocyanin constituents in

  2. Exceptionally Fast Uptake and Metabolism of Cyanidin 3Glucoside by Rat Kidneys and Liver

    Microsoft Academic Search

    Andreja Vanzo; Urska Vrhovsek; Federica Tramer; Fulvio Mattivi; Sabina Passamonti

    2011-01-01

    To asses the hypothesis that anthocyanins are rapidly taken up from the blood into tissues, where they accumulate up to their bioactivity threshold, an intravenous dose of cyanidin 3-glucoside (1) was administered to anaesthetized rats. Cyanidin 3-glucoside (1) and its metabolites were analyzed in the plasma, kidneys, liver, urine, and bile, using last-generation mass spectrometry. Compound 1 was found to

  3. Water-soluble constituents of caraway: carvone derivatives and their glucosides.

    PubMed

    Matsumura, Tetsuko; Ishikawa, Toru; Kitajima, Junichi

    2002-01-01

    Nine monoterpenoids related to carvone and seven glucosides were isolated from the water-soluble portion of the methanolic extract of the caraway (fruit of Carum carvi L.), and their structures were clarified by spectral investigation. Among them, eight monoterpenoids and six glucosides were new. PMID:11824587

  4. Oviposition Stimulant for a Gall-Inducing Sawfly, Euura lasiolepis , on Willow is a Phenolic Glucoside

    Microsoft Academic Search

    Heikki Roininen; Peter W. Price; Riitta Julkunen-Tiitto; Jorma Tahvanainen; Arsi Ikonen

    1999-01-01

    The ovipositional stimulation for the shoot galling sawfly, Euura lasiolepis, whose natural host is the North American willow, Salix lasiolepis, was studied in response to its original host, Finnish willows, poplar species, and individual phenolic glucosides and fractions. The major phenolic glucosides in the natural host were salicortin and tremulacin, which were also the major components in the Finnish S.

  5. Colorimetric Method for the Estimation of Total Limonoid Aglycones and Glucoside Contents in Citrus Juices

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A method for estimating the total limonoid aglycone and glucoside concentrations in Citrus samples in terms of limonin and limonin glucoside equivalents is presented. The method consists of extraction followed by colorimetric quantification. The colorimetric quantification was based on the formatio...

  6. Anomericity of T-2 toxin-glucoside: masked mycotoxin in cereal crops.

    PubMed

    McCormick, Susan P; Kato, Takayuki; Maragos, Chris M; Busman, Mark; Lattanzio, Veronica M T; Galaverna, Gianni; Dall-Asta, Chiara; Crich, David; Price, Neil P J; Kurtzman, Cletus P

    2015-01-21

    T-2 toxin is a trichothecene mycotoxin produced when Fusarium fungi infect grains, especially oats and wheat. Ingestion of T-2 toxin contaminated grain can cause diarrhea, hemorrhaging, and feed refusal in livestock. Cereal crops infected with mycotoxin-producing fungi form toxin glycosides, sometimes called masked mycotoxins, which are a potential food safety concern because they are not detectable by standard approaches and may be converted back to the parent toxin during digestion or food processing. The work reported here addresses four aspects of T-2 toxin-glucosides: phytotoxicity, stability after ingestion, antibody detection, and the anomericity of the naturally occurring T-2 toxin-glucoside found in cereal plants. T-2 toxin-?-glucoside was chemically synthesized and compared to T-2 toxin-?-glucoside prepared with Blastobotrys muscicola cultures and the T-2 toxin-glucoside found in naturally contaminated oats and wheat. The anomeric forms were separated chromatographically and differ in both NMR and mass spectrometry. Both anomers were significantly degraded to T-2 toxin and HT-2 toxin under conditions that mimic human digestion, but with different kinetics and metabolic end products. The naturally occurring T-2 toxin-glucoside from plants was found to be identical to T-2 toxin-?-glucoside prepared with B. muscicola. An antibody test for the detection of T-2 toxin was not effective for the detection of T-2 toxin-?-glucoside. This anomer was produced in sufficient quantity to assess its animal toxicity. PMID:25520274

  7. Use of Near-Infrared Spectroscopy for Estimating Lignan Glucosides Contents in Intact Sesame Seeds

    Microsoft Academic Search

    Kwan Su Kim; Si Hyung Park; Su Noh Ryu

    Near-infrared spectroscopy (NIRS) was used to develop a rapid and efficient method to determine lignan glucosides in intact seeds of sesame (Sesamum indicum L.) germplasm accessions in Korea. A total of 93 samples (about 2 g of intact seeds) were scanned in the reflectance mode of a scanning monochromator, and the reference values for lignan glucosides contents were measured by

  8. Indole-glucosides as novel sodium glucose co-transporter 2 (SGLT2) inhibitors. Part 2

    Microsoft Academic Search

    Xiaoyan Zhang; Maud Urbanski; Mona Patel; Geoffrey G. Cox; Roxanne E. Zeck; Haiyan Bian; Bruce R. Conway; Mary Pat Beavers; Philip J. Rybczynski; Keith T. Demarest

    2006-01-01

    A series of indole-O-glucosides and C-glucosides was synthesized and evaluated in SGLT1 and SGLT2 cell-based functional assays. Compounds 2a and 2o were identified as potent SGLT2 inhibitors and screened in ZDF rats.

  9. New ?-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam.

    PubMed

    Kashiwada, Yoshiki; Ahmed, Fakhruddin Ali; Kurimoto, Shin-ichiro; Kim, Sang-Yong; Shibata, Hirofumi; Fujioka, Toshihiro; Takaishi, Yoshihisa

    2012-01-01

    Two new caffeoyl quinic acid ?-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides, were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4'-O-?-D-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3'-O-?-D-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses. PMID:21748486

  10. A pair of new atropisomeric cupressuflavone glucosides isolated from Juniperus communis var. depressa

    Microsoft Academic Search

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

    2005-01-01

    A pair of new atropisomers, (M)- and (P)-cupressuflavone 4?-O-?-d-glucoside, were isolated from Juniperus communis var. depressa, and their absolute structures and axial configurations were determined using 2D NMR and circular dichroism. These are the first reported stable (M)- and (P)-isomers of cupressuflavone glucosides isolated from natural sources.

  11. Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya.

    PubMed

    Seigler, David S; Pauli, Guido F; Nahrstedt, Adolf; Leen, Rosemary

    2002-08-01

    Leaf and stem material of Passiflora edulis (Passifloraceae) contains the new cyanogenic glycosides (2R)-beta-D-allopyranosyloxy-2-phenylacetonitrile (1a) and (2S)-beta-D-allopyranosyloxy-2-phenylacetonitrile (1b), along with smaller amounts of (2R)-prunasin (2a), sambunigrin (2b), and the alloside of benzyl alcohol (4); the major cyanogens of the fruits are (2R)-prunasin (2a) and (2S)-sambunigrin (2b). The major cyanogenic glycoside of Carica papaya (Caricaceae) is 2a; only small amounts of 2b also are present. We were not able to confirm the presence of a cyclopentenoid cyanogenic glycoside, tetraphyllin B, in Carica papaya leaf and stem materials. In detailed 1H NMR studies of 1a/b and 2a/b, differences in higher order effects in glucosides and allosides proved to be valuable for assignment of structures in this series. The diagnostic chemical shifts of cyanogenic methine and anomeric protons in 1a/b are sensitive to anisotropic environmental effects. The assignment of C-2 stereochemistry of 1a/b was made in analogy to previous assignments in the glucoside series and was supported by GLC analysis of the TMS ethers. PMID:12150815

  12. 2'-O-(8-Hydroxy-2,6-dimethyl-2(E),6(E)-octadienoyl)-dihydropenstemide, a new iridoid glycoside from Penstemon confertus.

    PubMed

    Gering-Ward, B

    1989-02-01

    A new iridoid glycoside, 2'- O-(8-hydroxy-2,6-dimethyl-2( E),6( E)-octadienoyl)-dihydropenstemide, has been isolated from PENSTEMON CONFERTUS Dougl. Its structure was elucidated by FD-mass, (1)H-NMR, and (13)C-NMR spectroscopy. PMID:17262262

  13. Effect of the temperature and the exclusion of UVB radiation on the phenolics and iridoids in Menyanthes trifoliata L. leaves in the subarctic

    Microsoft Academic Search

    Françoise Martz; Minna Turunen; Riitta Julkunen-Tiitto; Kaisa Lakkala; Marja-Liisa Sutinen

    2009-01-01

    The long-term effects of UVB exclusion and temperature on the methanol extractable (ME) phenolics (flavonoids, phenolic acids) and iridoids of Menyanthes trifoliata L. (Mt) leaves were studied in northern Finland (68°N) using wooden frames covered with filters for UVB exclusion (polyester filter), control (cellulose acetate filter) and ambient (no filter) conditions. Analysis of ambient plots showed no effect of the

  14. Galloyl, caffeoyl and hexahydroxydiphenoyl esters of dihydrochalcone glucosides from Balanophora tobiracola.

    PubMed

    Tanaka, Takashi; Uehara, Rami; Nishida, Kaori; Kouno, Isao

    2005-03-01

    Seven galloyl, caffeoyl and (S)-hexahydroxydiphenoyl (HHDP) esters of dihydrochalcone glucosides were isolated from Balanophora tobiracola; based on spectroscopic and chemical evidence, their structures were determined to be 6''-O-galloyl-, 3'',4''-di-O-galloyl-, 4'',6''-di-O-galloyl-, 4'',6''-O-(S)-HHDP-, 3''-O-galloyl-4'',6''-O-(S)-HHDP-, 3''-O-caffeoyl-4'',6''-O-(S)-HHDP-3-hydroxyphloretin 4'-O-beta-D-glucosides and 3''-O-galloyl-4'',6''-O-(S)-HHDP-phloretin 4'-O-beta-D-glucoside, respectively. By contrast, these compounds were not found in the taxonomically related B. japonica. The 3''-galloyl-4'',6''-HHDP esters of the dihydrochalcone glucosides showed strong inhibitory activities against alpha-glucosidase. Four known compounds were also isolated namely, (+/-)-eriodictyol 7-O-beta-D-glucoside, 1-O-caffeoyl-3-O-galloyl-beta-D-glucose, phloretin 4'-O-beta-D-glucoside, and 3-hydroxyphloretin 4'-O-beta-D-glucoside. PMID:15771889

  15. Chemotaxonomic value of magastigmane glucosides of Cichorium calvum.

    PubMed

    Michalska, Klaudia; Beharav, Alex; Kisiel, Wanda

    2014-03-01

    Morphological characters and molecular analyses of Cichorium calvum and C. pumilum do not allow clear discrimination between these closely related wild species. Therefore, the aim of this study was to characterize the secondary metabolites of C. calvum and to select chemical markers which are unique to this species. From roots of C. calvum, ten sesquiterpene lactones were isolated, including seven lactucin-type guaianolides reported earlier from C. pumilum. Aerial parts also afforded secondary metabolites common to both species, along with the megastigmane glucosides staphylionoside D, saussureoside B and komaroveside A. This is the first report of the occurrence of these norisoprenoids in Cichorium species and the second record of their isolation from plants. Therefore, chemical discrimination of C. calvum is possible on the basis of its norisoprenoid composition. PMID:24689202

  16. Regioselective glucosidation of trans-resveratrol in Escherichia coli expressing glucosyltransferase from Phytolacca americana.

    PubMed

    Ozaki, Shin-ichi; Imai, Hiroya; Iwakiri, Tomoya; Sato, Takehiro; Shimoda, Kei; Nakayama, Toru; Hamada, Hiroki

    2012-03-01

    A glucosyltransferase (GT) of Phytolacca americana (PaGT3) was expressed in Escherichia coli and purified for the synthesis of two O-?-glucoside products of trans-resveratrol. The reaction was moderately regioselective with a ratio of 4'-O-?-glucoside: 3-O-?-glucoside at 10:3. We used not only the purified enzyme but also the E. coli cells containing the PaGT3 gene for the synthesis of glycoconjugates. E. coli cell cultures also have other advantages, such as a shorter incubation time compared with cultured plant cells, no need for the addition of exogenous glucosyl donor compounds such as UDP-glucose, and almost complete conversion of the aglycone to the glucoside products. Furthermore, a homology model of PaGT3 and mutagenesis studies suggested that His-20 would be a catalytically important residue. PMID:22048846

  17. Galloyl, caffeoyl and hexahydroxydiphenoyl esters of dihydrochalcone glucosides from Balanophora tobiracola

    Microsoft Academic Search

    Takashi Tanaka; Rami Uehara; Kaori Nishida; Isao Kouno

    2005-01-01

    Seven galloyl, caffeoyl and (S)-hexahydroxydiphenoyl (HHDP) esters of dihydrochalcone glucosides were isolated from Balanophora tobiracola; based on spectroscopic and chemical evidence, their structures were determined to be 6?-O-galloyl-, 3?,4?-di-O-galloyl-, 4?,6?-di-O-galloyl-, 4?,6?-O-(S)-HHDP-, 3?-O-galloyl-4?,6?-O-(S)-HHDP-, 3?-O-caffeoyl-4?,6?-O-(S)-HHDP-3-hydroxyphloretin 4?-O-?-d-glucosides and 3?-O-galloyl-4?,6?-O-(S)-HHDP-phloretin 4?-O-?-d-glucoside, respectively. By contrast, these compounds were not found in the taxonomically related B. japonica. The 3?-galloyl-4?,6?-HHDP esters of the dihydrochalcone glucosides showed strong

  18. Thesinine-4?- O-?- d-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis

    Microsoft Academic Search

    Martina Herrmann; Holger Joppe; Gerhard Schmaus

    2002-01-01

    The glycosylated pyrrolizidine alkaloid, thesinine-4?-O-?-d-glucoside, has been isolated from the aqueous methanolic extract of dried seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analyses.

  19. Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.

    PubMed

    Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

    2002-06-01

    The glycosylated pyrrolizidine alkaloid, thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analysis. PMID:12031432

  20. New acetophenone glucosides isolated from extracts of Helichrysum italicum with antiinflammatory activity.

    PubMed

    Sala, A; Recio, M C; Giner, R M; Máñez, S; Ríos, J L

    2001-10-01

    Three new acetophenone glucosides (4-6), three known aglycons (1-3), and a benzo-gamma-pyrone glucoside (7) were isolated from the CH(2)Cl(2), EtOAc, and BuOH extracts from the aerial parts of Helichrysum italicum. All the compounds tested showed antiinflammatory activity in a 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced mouse ear edema test, and the ID(50) value of compound 2, the most active compound, was determined. PMID:11678669

  1. Accumulation of peonidin 3-glucoside enhanced by osmotic stress in grape (Vitis vinifera L.) cell suspension

    Microsoft Academic Search

    Chi Bao Do; François Cormier

    1991-01-01

    Cell cultures of grapes, Vitis vinifera L. cv Gamay Fréaux were grown under different conditions of external osmotic potential induced by an increase of sucrose concentration or by the addition of mannitol to the culture medium. Addition of 82 mM mannitol or increasing sucrose concentration to 132 mM had similar effects on repressing growth. Cyanidin 3-glucoside, peonidin 3-glucoside and peonidin

  2. Cyanidin 3-glucoside accumulation in plane tree (Platanus acerifolia) cell-suspension cultures

    Microsoft Academic Search

    Ibtissam Alami; Alain Clérivet

    2000-01-01

    The accumulation of only one anthocyanin, cyanidin 3-glucoside, in cell-suspension cultures of plane tree (Platanus aceriflia) is reported for the first time. During a time span of 6 years, no new anthocyanin was detected and cyanidin 3-glucoside was maintained at about 35 mg l-1 cell culture medium. This stable cell culture system could therefore be used for the biotechnological production of cyanidin

  3. Flavonoid 5-glucosides from the cocoon shell of the silkworm, Bombyx mori

    Microsoft Academic Search

    Yasumori Tamura; Ken-ichi Nakajima; Ken-ichi Nagayasu; Chiyuki Takabayashi

    2002-01-01

    The flavonoid 5-glucosides, quercetin 5,4?-di-O-?-d-glucopyranoside and quercetin 5,7,4?-tri-O-?-d-glucopyranoside, together with the known quercetin 5-O-?-d-glucopyranoside, were isolated from the cocoon shell of the silkworm, Bombyx mori. The structures were identified by spectroscopic analysis. These flavonoid glucosides were not present in mulberry leaves, the silkworm's only food, and they are considered to be metabolites produced by the silkworm.

  4. 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

  5. Dihydrochalcone glucosides and antioxidant activity from the roots of Anneslea fragrans var. lanceolata.

    PubMed

    Huang, Hung-Yi; Ko, Horng-Huey; Jin, Yu-Jin; Yang, Sheng-Zehn; Shih, You-An; Chen, Ih-Sheng

    2012-06-01

    Bioassay-guided fractionation of the roots of Anneslea fragrans var. lanceolata led to the isolation of four dihydrochalcone glucosides, davidigenin-2'-O-(6?-O-4?'-hydroxybenzoyl)-?-glucoside (1), davidigenin-2'-O-(2?-O-4?'-hydroxybenzoyl)-?-glucoside (2), davidigenin-2'-O-(3?-O-4?'-hydroxybenzoyl)-?-glucoside (3), and davidigenin-2'-O-(6?-O-syringoyl)-?-glucoside (4), and 13 known compounds. The structures were identified by means of spectroscopic analysis. Davidigenin-2'-O-(6?-O-syringoyl)-?-glucoside (4), 1-O-3,4-dimethoxy-5-hydroxyphenyl-6-O-(3,5-di-O-methylgalloyl)-?-glucopyranoside (5), lyoniresinol (10), and syringic acid (13) showed ABTS [2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)] cation radical scavenging activity, with SC(50) values of 52.6 ± 5.5, 26.0 ± 0.7, 6.0 ± 0.2, and 27.5 ± 0.6 ?g/mL in 20 min, respectively. Lyoniresinol (10), isofraxidin (12), and syringic acid (13) also showed DPPH [1,1-diphenyl-2-picrylhydrazyl] radical scavenging activity, with SC(50) values of 8.4 ± 1.8, 51.6 ± 2.2, and 4.3 ± 0.7 ?g/mL in 30 min, respectively. PMID:22459967

  6. Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides.

    PubMed

    Park, Hye-Yeon; Kim, Mihyang; Han, Jaehong

    2011-08-01

    A Gram-negative anaerobic microorganism, MRG-1, isolated from human intestine showed high activities of deglycosylation and reduction of daidzin, based on rapid TLC analysis. A rod-shaped strain MRG-1 was identified as a new species showing 91.0% homology to Coprobacillus species, based on 16S rRNA sequence analysis. The strain MRG-1 showed ?-glucosidase activity toward daidzin and genistin, and daidzein and genistein were produced, respectively. However, the strain MRG-1 did not react with flavone glycosides, flavanone glycosides, and isoflavone C-glucoside. Besides, MRG-1 showed stereoselective reductase activity to isoflavone, daidzein, genistein, 7-hydroxyisoflavone, and formononetin, resulting in the formation of corresponding R-isoflavanone enantiomers. The new isoflavanones of 7-hydroxyisoflavanone and dihydroformononetin were characterized by NMR, and the absolute configurations of the enantiomers were determined with CD spectroscopy. The kinetic study of the anaerobic biotransformation showed both activities were exceptionally fast compared to the reported conversion by other anaerobic bacteria. PMID:21562980

  7. Low toxicity of deoxynivalenol-3-glucoside in microbial cells.

    PubMed

    Suzuki, Tadahiro; Iwahashi, Yumiko

    2015-01-01

    Host plants excrete a glucosylation enzyme onto the plant surface that changes mycotoxins derived from fungal secondary metabolites to glucosylated products. Deoxynivalenol-3-glucoside (DON3G) is synthesized by grain uridine diphosphate-glucosyltransferase, and is found worldwide, although information on its toxicity is lacking. Here, we conducted growth tests and DNA microarray analysis to elucidate the characteristics of DON3G. The Saccharomyces cerevisiae PDR5 mutant strain exposed to DON3G demonstrated similar growth to the dimethyl sulfoxide control, and DNA microarray analysis revealed limited differences. Only 10 genes were extracted, and the expression profile of stress response genes was similar to that of DON, in contrast to metabolism genes like SER3, which encodes 3-phosphoglycerate dehydrogenase. Growth tests with Chlamydomonas reinhardtii also showed a similar growth rate to the control sample. These results suggest that DON3G has extremely low toxicity to these cells, and the glucosylation of mycotoxins is a useful protective mechanism not only for host plants, but also for other species. PMID:25609182

  8. Tetrahydroxystilbene Glucoside Attenuates Neuroinflammation through the Inhibition of Microglia Activation

    PubMed Central

    Zhang, Feng; Wang, Yan-Ying; Yang, Jun; Lu, Yuan-Fu; Liu, Jie; Shi, Jing-Shan

    2013-01-01

    Neuroinflammation is closely implicated in the pathogenesis of neurological diseases. The hallmark of neuroinflammation is the microglia activation. Upon activation, microglia are capable of producing various proinflammatory factors and the accumulation of these factors contribute to the neuronal damage. Therefore, inhibition of microglia-mediated neuroinflammation might hold potential therapy for neurological disorders. 2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component extracted from Polygonum multiflorum, is reported to be beneficial for human health with a great number of pharmacological properties including antioxidant, free radical-scavenging, anti-inflammation, antilipemia, and cardioprotective effects. Recently, TSG-mediated neuroprotective effects have been well demonstrated. However, the neuroprotective actions of TSG on microglia-induced neuroinflammation are not known. In the present study, microglia BV2 cell lines were applied to investigate the anti-neuroinflammatory effects of TSG. Results showed that TSG reduced LPS-induced microglia-derived release of proinflammatory factors such as TNF?, IL-1?, and NO. Moreover, TSG attenuated LPS-induced NADPH oxidase activation and subsequent reactive oxygen species (ROS) production. Further studies indicated that TSG inhibited LPS-induced NF-?B signaling pathway activation. Together, TSG exerted neuroprotection against microglia-mediated neuroinflammation, suggesting that TSG might present a promising benefit for neurological disorders treatment. PMID:24349614

  9. O-Spiro C-aryl glucosides as novel sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors

    Microsoft Academic Search

    Baihua Xu; Binhua Lv; Yan Feng; Ge Xu; Jiyan Du; Ajith Welihinda; Zelin Sheng; Brian Seed; Yuanwei Chen

    2009-01-01

    Two series of O-spiro C-aryl glucosides were synthesized and tested for inhibition of hSGLT1 and hSGLT2. 6?-O-Spiro C-aryl glucosides exhibited potent in vitro hSGLT2 inhibitory activity but 2?-O-spiro C-aryl glucosides showed no in vitro hSGLT2 inhibitory activity at a screening concentration of 1?M.

  10. Iridoid Glycoside Variation in the Invasive Plant Dalmatian Toadflax, Linaria dalmatica (Plantaginaceae), and Sequestration by the Biological Control Agent, Calophasia lunula

    Microsoft Academic Search

    Mary A. Jamieson; M. Deane Bowers

    2010-01-01

    Invasive plant species can have significant ecological and economic impacts. Although numerous hypotheses highlight the importance\\u000a of the chemical defenses of invasive plant species, the chemical ecology of many invasive plants has not yet been investigated.\\u000a In this study, we provide the first quantitative investigation of variation in iridoid glycoside concentrations of the invasive\\u000a plant Dalmatian toadflax (Linaria dalmatica). We

  11. On the glucoside analysis: simultaneous determination of free and esterified steryl glucosides in olive oil. Detailed analysis of standards as compulsory first step.

    PubMed

    Gómez-Coca, Raquel B; Pérez-Camino, María Del Carmen; Moreda, Wenceslao

    2013-11-15

    This work covers two important gaps in the field of micronutrient databases: herein we describe a short and easy protocol that allows the analysis of both free and esterified steryl gulcosides in olive oil. By utilising accurate quantitative methods we achieve a better understanding of olive oil composition and health promoting properties. The procedure consists of isolating the fraction of interest through solid phase extraction, and using gas chromatography-flame ionisation detection for both identification and quantification of the derivatised species. Additionally, mass-spectrometry detection has been utilised for confirming the identity of the individual esterified steryl glucosides in some cases. The method's limit of detection has been set at 0.37mg/kg for each free steryl glucoside and 0.20mg/kg for each esterified steryl glucoside, whereas the recoveries are around 96% and 77%, respectively. Finally, we provide a complete analysis of the commercial standard for esterified steryl glucosides, since such information was not yet available. PMID:23790913

  12. Uptake of quercetin and quercetin 3-glucoside from whole onion and apple peel extracts by Caco-2 cell monolayers.

    PubMed

    Boyer, Jeanelle; Brown, Dan; Liu, Rui Hai

    2004-11-17

    Evidence suggests that regular consumption of fruits and vegetables may reduce the risk of chronic diseases, and phytochemicals from fruits and vegetables may be responsible for this health benefit. However, there is limited knowledge on the bioavailability of specific phytochemicals from whole fruits and vegetables. This study used Caco-2 cells to examine uptake of quercetin aglycon and quercetin 3-glucoside as purified compounds and from whole onion and apple peel extracts. Pure quercetin aglycon was absorbed by the Caco-2 cells in higher concentrations than quercetin 3-glucoside (p < 0.05). Caco-2 cells treated with quercetin 3-glucoside accumulated both quercetin 3-glucoside and quercetin. Caco-2 cells absorbed more onion quercetin aglycon than onion quercetin 3-glucoside (p < 0.05), and the percentage of onion quercetin absorbed was greater than that of pure quercetin, most likely due to enzymatic hydrolysis of quercetin 3-glucoside and other quercetin glucosides found in the onion by the Caco-2 cells. Caco-2 cells absorbed low levels of quercetin 3-glucoside from apple peel extracts, but quercetin aglycon absorption was not detected. Caco-2 cell homogenates demonstrated both lactase and glucosidase activities when incubated with lactose and quercetin 3-glucoside, respectively. This use of the Caco2 cell model appears to be a simple and useful system for studying bioavailability of whole food phytochemicals and may be used to assess differences in bioavailability between foods. PMID:15537334

  13. Importance of phenolic glucosides in host selection of shoot galling sawfly,Euura amerinae, onSalix pentandra.

    PubMed

    Kolehmainen, J; Roininen, H; Julkunen-Tiitto, R; Tahvanainen, J

    1994-09-01

    The effects of phenolic glucosides on the oviposition behavior ofEuura amerinae L. (Hymenoptera: Tenthredinidae) were tested in multiple oviposition experiments using different shoot length categories ofSalix pentandra L. (with different amounts of phenolic glucosides) and in experiments with pure phenolic glucosides (salidroside, arbutin, salicin, 90% salicortin, 90% 2'-O-acetylsalicortin) or composite total fractions of phenolic glucosides from three willow species (S. pentandra, S. myrsinifolia Salisb.,S. triandra L.). This was the first time that the effects of pure phenolic glucosides on the oviposition behavior of sawfly species were tested. Total fraction of phenolic glucosides fromS. pentandra and its main individual glucoside, 2'-O-acetyl-salicortin, stimulated the strongest ovipositional behavior inE. amerinae. The results show clearly that females ofE. amerinae can recognize and choose their host willow,S. pentandra, on the basis of phenolic glucosides. Moreover, they are probably able to use phenolic glucosides as a cue in shoot selection within host-plant individuals. PMID:24242817

  14. The bHLH transcription factor BIS1 controls the iridoid branch of the monoterpenoid indole alkaloid pathway in Catharanthus roseus.

    PubMed

    Van Moerkercke, Alex; Steensma, Priscille; Schweizer, Fabian; Pollier, Jacob; Gariboldi, Ivo; Payne, Richard; Vanden Bossche, Robin; Miettinen, Karel; Espoz, Javiera; Purnama, Purin Candra; Kellner, Franziska; Seppänen-Laakso, Tuulikki; O'Connor, Sarah E; Rischer, Heiko; Memelink, Johan; Goossens, Alain

    2015-06-30

    Plants make specialized bioactive metabolites to defend themselves against attackers. The conserved control mechanisms are based on transcriptional activation of the respective plant species-specific biosynthetic pathways by the phytohormone jasmonate. Knowledge of the transcription factors involved, particularly in terpenoid biosynthesis, remains fragmentary. By transcriptome analysis and functional screens in the medicinal plant Catharanthus roseus (Madagascar periwinkle), the unique source of the monoterpenoid indole alkaloid (MIA)-type anticancer drugs vincristine and vinblastine, we identified a jasmonate-regulated basic helix-loop-helix (bHLH) transcription factor from clade IVa inducing the monoterpenoid branch of the MIA pathway. The bHLH iridoid synthesis 1 (BIS1) transcription factor transactivated the expression of all of the genes encoding the enzymes that catalyze the sequential conversion of the ubiquitous terpenoid precursor geranyl diphosphate to the iridoid loganic acid. BIS1 acted in a complementary manner to the previously characterized ethylene response factor Octadecanoid derivative-Responsive Catharanthus APETALA2-domain 3 (ORCA3) that transactivates the expression of several genes encoding the enzymes catalyzing the conversion of loganic acid to the downstream MIAs. In contrast to ORCA3, overexpression of BIS1 was sufficient to boost production of high-value iridoids and MIAs in C. roseus suspension cell cultures. Hence, BIS1 might be a metabolic engineering tool to produce sustainably high-value MIAs in C. roseus plants or cultures. PMID:26080427

  15. Cellular uptake of dietary flavonoid quercetin 4'-beta-glucoside by sodium-dependent glucose transporter SGLT1.

    PubMed

    Walgren, R A; Lin, J T; Kinne, R K; Walle, T

    2000-09-01

    Although it has been suggested that the intestinal glucose transporter may actively absorb dietary flavonoid glucosides, there is a lack of direct evidence for their transport by this system. In fact, our previous studies with the human Caco-2 cell model of intestinal absorption demonstrated that a major dietary flavonoid, quercetin 4'-beta-glucoside, is effluxed by apically expressed multidrug resistance-associated protein-2, potentially masking evidence for active absorption. The objective of this study was to test the hypothesis that quercetin 4'-beta-glucoside is a substrate for the intestinal sodium-dependent D-glucose cotransporter SGLT1. Cellular uptake of quercetin 4'-beta-glucoside was examined with Caco-2 cells and SGLT1 stably transfected Chinese hamster ovary cells (G6D3 cells). Although quercetin 4'-beta-glucoside is not absorbed across Caco-2 cell monolayers, examination of the cells by indirect fluorescent microscopy as well as by HPLC analysis of cellular content revealed cellular accumulation of this glucoside after apical loading. Consistent with previous observations, the accumulation of quercetin 4'-beta-glucoside in both Caco-2 and G6D3 cells was markedly enhanced in the presence of multidrug resistance-associated protein inhibition. Uptake of quercetin 4'-beta-glucoside was greater in SGLT1-transfected cells than in parental Chinese hamster ovary cells. Uptake of the glucoside by Caco-2 and G6D3 cells was sodium-dependent and was inhibited by the monovalent ionophore nystatin. In both Caco-2 and G6D3 cells, quercetin 4'-beta-glucoside uptake was inhibited by 30 mM glucose and 0.5 mM phloridzin. These results demonstrate for the first time that quercetin 4'-beta-glucoside is transported by SGLT1 across the apical membrane of enterocytes. PMID:10945831

  16. 2-methylnaphthazarin 5- O-glucoside from the methanol extracts of in vitro cultures of Drosera species

    Microsoft Academic Search

    Jaromir Budzianowski

    1997-01-01

    The methanol extracts of Drosera rotundifolia and D. spathulata obtained by in vitro micropropagation yielded the new pigment 2-methylnaphthazarin (5,8-dihydroxy-2-methyl-1,4-naphthoquinone) 5-O-glucoside, which is an artefact formed from rossoliside (7-methylhydrojuglone 4-O-glucoside) during extraction with methanol.

  17. Comparison of Stevia plants grown from seeds, cuttings and stem-tip cultures for growth and sweet diterpene glucosides

    Microsoft Academic Search

    Yukiyoshi Tamura; Shigeharu Nakamura; Hiroshi Fukui; Mamoru Tabata

    1984-01-01

    The growth and sweet diterpene glucosides of Stevia plants propagated by stem-tip cultures were compared with those of the control plants propagated by seeds. There was no significant difference between the two groups both in growth and in chemical composition. As for the contents of sweet diterpene glucosides, however, the clonal plants showed significantly smaller variations than the sexually propagated

  18. Sequestration, tissue distribution and developmental transmission of cyanogenic glucosides in a specialist insect herbivore.

    PubMed

    Zagrobelny, Mika; Olsen, Carl Erik; Pentzold, Stefan; Fürstenberg-Hägg, Joel; Jørgensen, Kirsten; Bak, Søren; Møller, Birger Lindberg; Motawia, Mohammed Saddik

    2014-01-01

    Considering the staggering diversity of bioactive natural products present in plants, insects are only able to sequester a small number of phytochemicals from their food plants. The mechanisms of how only some phytochemicals are sequestered and how the sequestration process takes place remains largely unknown. In this study the model system of Zygaena filipendulae (Lepidoptera) and their food plant Lotus corniculatus is used to advance the knowledge of insect sequestration. Z. filipendulae larvae are dependent on sequestration of the cyanogenic glucosides linamarin and lotaustralin from their food plant, and have a much lower fitness if reared on plants without these compounds. This study investigates the fate of the cyanogenic glucosides during ingestion, sequestration in the larvae, and in the course of insect ontogeny. To this purpose, double-labeled linamarin and lotaustralin were chemically synthesized carrying two stable isotopes, a (2)H labeled aglucone and a (13)C labeled glucose moiety. In addition, a small amount of (14)C was incorporated into the glucose residue. The isotope-labeled compounds were applied onto cyanogenic L. corniculatus leaves that were subsequently presented to the Z. filipendulae larvae. Following ingestion by the larvae, the destiny of the isotope labeled cyanogenic glucosides was monitored in different tissues of larvae and adults at selected time points, using radio-TLC and LC-MS analyses. It was shown that sequestered compounds are taken up intact, contrary to earlier hypotheses where it was suggested that the compounds would have to be hydrolyzed before transport across the gut. The uptake from the larval gut was highly stereo selective as the ?-glucosides were retained while the ?-glucosides were excreted and recovered in the frass. Sequestered compounds were rapidly distributed into all analyzed tissues of the larval body, partly retained throughout metamorphosis and transferred into the adult insect where they were distributed to all tissues. During subsequent mating, isotope labeled cyanogenic glucosides were transferred from the male to the female in the nuptial gift. PMID:24269868

  19. Triacylated cyanidin 3-(3 X-glucosylsambubioside)-5-glucosides from the flowers of Malcolmia maritima

    Microsoft Academic Search

    Fumi Tatsuzawa; Norio Saito; Kenjiro Toki; Koichi Shinoda; Atsushi Shigihara; Toshio Honda

    2008-01-01

    Three acylated cyanidin 3-(3X-glucosylsambubioside)-5-glucosides (1–3) and one non-acylated cyanidin 3-(3X-glucosylsambubioside)-5-glucoside (4) were isolated from the purple-violet or violet flowers and purple stems of Malcolmia maritima (L.) R. Br (the Cruciferae), and their structures were determined by chemical and spectroscopic methods. In the flowers of this plant, pigment 1 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(?-d-glucopyranosyl)-?-d-xylopyranosyl)-6-O-(trans-p-coumaroyl)-?-d-glucopyranoside]-5-O-[6-O-(malonyl)-(?-d-glucopyranoside) as a major pigment, and a

  20. Oxidation products of cyanidin 3- O -?- d -glucoside with a free radical initiator

    Microsoft Academic Search

    Takanori Tsuda; Katsumi Ohshima; Shunro Kawakishi; Toshihiko Osawa

    1996-01-01

    Recently, we have reported that anthocyanins show strong antioxidative activity, but no attention has been paid to anthocyanins\\u000a from the viewpoint of the reaction mechanism of alkylperoxyl radicals; therefore, we investigated the reaction products of\\u000a antioxidative anthocyanins (cyanidin 3-O-?-d-glucoside). Cyanidin 3-O-?-d-glucoside was reacted with 2,2?-azobis(2,4-dimet hylvaleronitrile) to generate the alkylperoxyl radicals, and the reaction\\u000a products were isolated by high-performance liquid

  1. Arabidopsis thaliana ?-glucosidase BGLU15 attacks flavonol 3-O-?-glucoside-7-O-?-rhamnosides.

    PubMed

    Roepke, Jonathon; Bozzo, Gale G

    2015-01-01

    Kaempferol and quercetin 3-O-?-glucoside-7-O-?-rhamnoside (K3G7R and Q3G7R, respectively) are major flavonol bisglycosides accumulating in Arabidopsis thaliana with synergistic abiotic stresses (i.e., nitrogen deficiency and low temperature, NDLT). However, these molecules disappear rapidly during recovery from NDLT. Typically, catabolism of related chemicals relies on ?-glucosidase (BGLU) action. Evidence for flavonol 3-O-?-glucoside-7-O-?-rhamnoside BGLU activity is provided here. Major losses of Q3G7R and K3G7R coincided with an approximate 250% induction in flavonol 3-O-?-glucoside-7-O-?-rhamnoside BGLU activity within 2days of NDLT recovery relative to plants cultured under nitrogen sufficiency and high temperature (NSHT, control). QTOF-MS/MS established the product of Q3G7R hydrolysis in the presence of Arabidopsis cell free extracts was quercetin 7-O-?-rhamnoside. A phylogenetic analysis of the Arabidopsis glycoside hydrolase family 1 identified BGLU15 (At2g44450) and five other members that cluster with Fabaceae hydrolases known to attack isoflavones and isoflavonoids, which are structurally somewhat related to flavonol 3-O-?-glucoside-7-O-?-rhamnosides. Real time quantitative PCR analysis established a 300% higher expression of BGLU15 within 1day of the recovery from NDLT relative to control plants; lower or negligible changes in expression were evident for the remaining BGLUs. Recombinant thioredoxin-His6-tagged mature BGLU15 protein was expressed in Escherichia coli and purified to homogeneity. A comparison of a wide spectrum of ?-glucosides showed that recombinant BGLU15 preferentially hydrolyses the 3-O-?-glucosides of flavonols, but does not attack quercetin 3-O-?-rhamnoside, quercetin 3-O-?-galactoside and rutin. BGLU15 displayed the highest catalytic efficiency for Q3G7R and K3G7R yielding their respective 7-O-rhamnosides as products; flavonol 3-O-glucosides were also attacked, albeit with lower efficiency. Together, it appears the loss of flavonol 3-O-?-glucoside-7-O-?-rhamnosides in Arabidopsis is dependent upon the enzyme-mediated cleavage of the 3-O-? linked glucose moiety. PMID:25468534

  2. Cyanidin 3-O-?-d-Glucoside Improves Bone Indices.

    PubMed

    Kaume, Lydia; Gilbert, William; Smith, Breda J; Devareddy, Latha

    2015-06-01

    Oxidative stress (OS) promotes bone loss after menopause, and there is evidence that dietary antioxidants may reduce the level of OS in vivo. This study examined dose-dependent effects of blackberries (BBs) containing mainly cyanidin 3-O-?-d-glucoside (C3G) in preventing bone loss in an ovariectomized (Ovx) rat model. Nine-month-old female (N=38) Sprague-Dawley rats were scanned using dual-energy X-ray absorptiometry for baseline whole body, bone mineral content (BMC), and bone mineral density (BMD). One group was sham operated (Sham) and three groups were ovariectomized (Ovx). The groups and corresponding diets were Sham+control diet (n=12), Ovx+control diet (n=12), Ovx+5% BB (n=7), and Ovx+10% BB (n=7). Control diet was AIN-93M rodent diet, and the Ovx+5% BB and Ovx+10% BB were a diet modified to contain powdered, freeze-dried BB at levels of 5% and 10% (w/w). Following 100 days of treatment, whole body BMC and BMD were reassessed and bone specimens, blood, and 24-h urine samples were collected for analyses. Findings indicate that ovariectomy (Ovx) compromised whole body BMC and trabecular microarchitecture of the proximal tibia and fourth lumbar vertebra. C3G-rich BB at the level of 5% modestly protected BMDs, loss of the tibia, lumbar vertebra, and femur by 2.4%, 2.7%, and 4.3% (P<.0013; .0437; .0004), respectively. BB 5% treatment significantly prevented loss of tibial trabecular bone volume and trabecular number by 37% and 21%, respectively (P<.05), and also significantly prevented tibial trabecular separation by 22%. We conclude that C3G-rich BB treatment at the level of 5% (w/w) but not at 10% (w/w) may modestly reduce Ovx-induced bone loss evident by improved tibial, vertebral, and femoral BMD values, and tibial bone microstructural parameters. Bone protective effects may be as a result of the synergistic effects of phenolic compounds; however, further work is required to determine BBs' specific mechanisms of action. PMID:25386839

  3. Metabolism of the masked mycotoxin deoxynivalenol-3-glucoside in pigs.

    PubMed

    Nagl, Veronika; Woechtl, Bettina; Schwartz-Zimmermann, Heidi Elisabeth; Hennig-Pauka, Isabel; Moll, Wulf-Dieter; Adam, Gerhard; Berthiller, Franz

    2014-08-17

    Plants can metabolize the Fusarium mycotoxin deoxynivalenol (DON) by forming the masked mycotoxin deoxynivalenol-3-?-D-glucoside (D3G). D3G might be cleaved during digestion, thus increasing the total DON burden of an individual. Due to a lack of in vivo data, D3G has not been included in the various regulatory limits established for DON so far. The aim of our study was to contribute to the risk assessment of D3G by determination of its metabolism in pigs. Four piglets received water, D3G (116 ?g/kg b.w.) and the equimolar amount of DON (75 ?g/kg b.w.) by gavage on day 1, 5 and 9 of the experiment, respectively. Additionally, 15.5 ?g D3G/kg b.w. were administered intravenously on day 13. Urine and feces were collected for 24 h and analyzed for DON, D3G, deoxynivalenol-3-glucuronide (DON-3-GlcA), deoxynivalenol-15-GlcA (DON-15-GlcA) and deepoxy-deoxynivalenol (DOM-1) by UHPLC-MS/MS. After oral application of DON and D3G, in total 84.8±9.7% and 40.3±8.5% of the given dose were detected in urine, respectively. The majority of orally administered D3G was excreted in form of DON, DON-15-GlcA, DOM-1 and DON-3-GlcA, while urinary D3G accounted for only 2.6±1.4%. In feces, just trace amounts of metabolites were found. Intravenously administered D3G was almost exclusively excreted in unmetabolized form via urine. Data indicate that D3G is nearly completely hydrolyzed in the intestinal tract of pigs, while the toxin seems to be rather stable after systemic absorption. Compared to DON, the oral bioavailability of D3G and its metabolites seems to be reduced by a factor of up to 2, approximately. PMID:24968060

  4. Characterization of kinetic and thermodynamic parameters of cyanidin-3-glucoside methyl and glucuronyl metabolite conjugates.

    PubMed

    Cruz, Luís; Basílio, Nuno; Mateus, Nuno; Pina, Fernando; de Freitas, Victor

    2015-02-01

    The determination of rate and equilibrium constants of anthocyanin metabolites with in vivo occurrence, cyanidin-4'-O-methyl-3-glucoside (Cy4'Me3glc) and cyanidin-7-O-glucuronyl-3-glucoside (Cy7Gluc3glc), was carried out for the first time by means of direct and reverse pH jumps. The thermodynamics and kinetics of these compounds are similar to the anthocyanin monoglucosides in particular for the analogous cyanidin-3-glucoside (Cy3glc) and peonidin-3-glucoside (Peo3glc). The rate and equilibrium constants of metabolites were also compared with malvin (malvidin 3,5-diglucoside) and with a bioinspired compound 3',4'-dihydroxy-7-O-glucopyranosyloxyflavylium (DGF). In Cy4'Me3glc and Cy7Gluc3glc the rate of hydration for a fixed pH value is slower than in DGF and the dominant species at moderately acidic solutions is the hemiketal. Oppositely, in DGF trans-chalcone is the dominant species at moderately acidic solutions. PMID:25622073

  5. Water-soluble constituents of caraway: aromatic compound, aromatic compound glucoside and glucides.

    PubMed

    Matsumura, Tetsuko; Ishikawa, Toru; Kitajima, Junichi

    2002-10-01

    From the water-soluble portion of the methanolic extract of caraway (fruit of Carum carvi L.), an aromatic compound, an aromatic compound glucoside and a glucide were isolated together with 16 known compounds. Their structures were clarified as 2-methoxy-2-(4'-hydroxyphenyl)ethanol, junipediol A 2-O-beta-D-glucopyranoside and L-fucitol, respectively. PMID:12377243

  6. Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.)

    PubMed Central

    Ko, Eun Young; Nile, Shivraj Hariram; Sharma, Kavita; Li, Guan Hao; Park, Se Won

    2014-01-01

    Quercetin and quercetin glucosides are the major flavonols present in onion (Allium cepa L.) and are predominantly present as quercetin, quercetin-3,4?-diglucoside and quercetin-4?-glucoside. Effect of different light wavelengths on onion after harvest and storage, with fluorescent, blue, red and ultra violet light influenced the quercetin and quercetin glucosides profile. In a peeled onion, all the light treatments elevated quercetin content in bulb. Among them, particularly fluorescent light effect was more eminent which stimulates the maximum synthesis of quercetin in onion. In case of whole onion bulb, skin and pulp showed different responses to light treatment, respectively. The pulp had the highest quercetin glucosides under blue light, whereas the lowest under fluorescent light. Onion skin showed nearly opposite pattern as compared to the pulp. In particular, light treatment proved to be a better way to increase the level of quercetin content in onions which might be utilized for industrial production of bioactive compounds from onion and onion waste products.

  7. Occurrence of Deoxynivalenol and Its Major Conjugate, Deoxynivalenol3Glucoside, in Beer and Some Brewing Intermediates

    Microsoft Academic Search

    Marta Kostelanska; Jana Hajslova; Milena Zachariasova; Alexandra Malachova; Kamila Kalachova; Jan Poustka; Jaromir Fiala; Peter M. Scott; Franz Berthiller; Rudolf Krska

    2009-01-01

    Since deoxynivalenol (DON), the main representative of Fusarium toxic secondary metabolites, is a relatively common natural contaminant in barley, its traces can be detected in many commercial beers. Our previous study reporting for the first time the occurrence of relatively high levels of DON- 3-glucoside (DON-3-Glc) in malt and beer prepared from relatively \\

  8. Vitamin B6 Status Indicators Decrease in Women Consuming a Diet High in Pyridoxine Glucoside1\\

    Microsoft Academic Search

    CHRISTINE M. HANSEN; JAMES E. LEKLEM; LORRAINE T. MILLER

    Previous research has shown that the pyridoxine glucoside (PNG) form of vitamin B-6 has a reduced bioavailability compared with pyridoxine, but its effect on vitamin B-6 status has not been assessed. Following an 8-d adjustment period, nine women con sumed diets containing a high or low amount of PNG for 18 d each, in a crossover design. The high and

  9. Water-soluble constituents of caraway: aromatic compound, aromatic compound glucoside and glucides

    Microsoft Academic Search

    Tetsuko Matsumura; Toru Ishikawa; Junichi Kitajima

    2002-01-01

    From the water-soluble portion of the methanolic extract of caraway (fruit of Carum carvi L.), an aromatic compound, an aromatic compound glucoside and a glucide were isolated together with 16 known compounds. Their structures were clarified as 2-methoxy-2-(4?-hydroxyphenyl)ethanol, junipediol A 2-O-?-d-glucopyranoside and l-fucitol, respectively.

  10. New p-menthanetriols and their glucosides from the fruit of caraway

    Microsoft Academic Search

    Tetsuko Matsumura; Toru Ishikawa; Junichi Kitajima

    2001-01-01

    Ten new p-menthanetriols, including eight stereoisomers of p-menthane-2,8,9-triol, and five new glucosides were isolated from the water-soluble portion of the methanol extract of the fruit of caraway (Carum carvi L.), which has been used as a spice and medicine. Their structures were clarified by spectral investigation.

  11. Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.).

    PubMed

    Ko, Eun Young; Nile, Shivraj Hariram; Sharma, Kavita; Li, Guan Hao; Park, Se Won

    2015-07-01

    Quercetin and quercetin glucosides are the major flavonols present in onion (Allium cepa L.) and are predominantly present as quercetin, quercetin-3,4'-diglucoside and quercetin-4'-glucoside. Effect of different light wavelengths on onion after harvest and storage, with fluorescent, blue, red and ultra violet light influenced the quercetin and quercetin glucosides profile. In a peeled onion, all the light treatments elevated quercetin content in bulb. Among them, particularly fluorescent light effect was more eminent which stimulates the maximum synthesis of quercetin in onion. In case of whole onion bulb, skin and pulp showed different responses to light treatment, respectively. The pulp had the highest quercetin glucosides under blue light, whereas the lowest under fluorescent light. Onion skin showed nearly opposite pattern as compared to the pulp. In particular, light treatment proved to be a better way to increase the level of quercetin content in onions which might be utilized for industrial production of bioactive compounds from onion and onion waste products. PMID:26150744

  12. A new sweet dihydrochalcone-glucoside from leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae).

    PubMed

    Qin, Xiang-Dong; Liu, Ji-Kai

    2003-01-01

    A new sweet dihydrochalcone-glucoside, trilobatin 2"-acetate (1), was isolated from the leaves of Lithocarpus pachyphyllus, together with phlorizin and trilobatin. The structures were established by spectroscopic methods, including one- and two-dimensional NMR (COSY, HMQC and HMBC). PMID:14577645

  13. Analysis of deoxynivalenol and deoxynivalenol-3-glucoside in hard red spring wheat inoculated with Fusarium graminearum

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Deoxynivalenol (DON) is a mycotoxin which isproduced by plant pathogens such as Fusarium species. The formation of the "masked" mycotoxin deoxinyvalenol-3-glucoside (D3G) results from a defense mechanism the plant uses for detoxification. These two mycotoxins are important from the food safety poi...

  14. Occurrence of deoxynivalenol and deoxynivalenol-3-glucoside in hard red spring wheat grown in the USA

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Deoxynivalenol (DON) is a mycotoxin found in wheat that is infected with Fusarium fungus. DON may also be converted to a type of "masked mycotoxin," named deoxynivalenol-3-glucoside (D3G), as a result of detoxification process of the plant. Both DON and D3G are known to be toxic. Due to the lack o...

  15. Kaempferol 7- O-rhamnoside-4?- O-glucoside from Pteridium aquilinum

    Microsoft Academic Search

    Filippo Imperato

    1998-01-01

    A new flavonol glycoside from aerial parts of Pteridium aquilinum was identified as kaempferol 7-O-rhamnoside-4?-O-glucoside by chemical and spectral methods. In addition a mixture of quercetin 3-O-fructoside and isoquercitrin was found in this plant material.

  16. Isoptaquiloside and caudatoside, illudane-type sesquiterpene glucosides from Pteridium aquilinum var. caudatum

    Microsoft Academic Search

    Uvidelio F. Castillo; Alistair L. Wilkins; Denis R. Lauren; Barry L. Smith; Neale R. Towers; Miguel E. Alonso-Amelot; Ramon Jaimes-Espinoza

    1997-01-01

    Ptaquiloside and two new illudane-type sesquiterpene glycosides were isolated from Pteridium aquilinum var. caudatum. One- and two-dimensional NMR analyses revealed the new glucosides to be isoptaquiloside and caudatoside. Four pterosins, A, B, K and Z, were also isolated from a base-acid treated extract.

  17. Helicobacter pylori Cholesteryl ?-Glucosides Contribute to Its Pathogenicity and Immune Response by Natural Killer T Cells

    PubMed Central

    Ito, Yuki; Vela, Jose Luis; Matsumura, Fumiko; Hoshino, Hitomi; Tyznik, Aaron; Lee, Heeseob; Girardi, Enrico; Zajonc, Dirk M.; Liddington, Robert; Kobayashi, Motohiro; Bao, Xingfeng; Bugaytsova, Jeanna; Borén, Thomas; Jin, Rongsheng; Zong, Yinong; Seeberger, Peter H.; Nakayama, Jun; Kronenberg, Mitchell; Fukuda, Minoru

    2013-01-01

    Approximately 10–15% of individuals infected with Helicobacter pylori will develop ulcer disease (gastric or duodenal ulcer), while most people infected with H. pylori will be asymptomatic. The majority of infected individuals remain asymptomatic partly due to the inhibition of synthesis of cholesteryl ?-glucosides in H. pylori cell wall by ?1,4-GlcNAc-capped mucin O-glycans, which are expressed in the deeper portion of gastric mucosa. However, it has not been determined how cholesteryl ?-glucosyltransferase (?CgT), which forms cholesteryl ?-glucosides, functions in the pathogenesis of H. pylori infection. Here, we show that the activity of ?CgT from H. pylori clinical isolates is highly correlated with the degree of gastric atrophy. We investigated the role of cholesteryl ?-glucosides in various aspects of the immune response. Phagocytosis and activation of dendritic cells were observed at similar degrees in the presence of wild-type H. pylori or variants harboring mutant forms of ?CgT showing a range of enzymatic activity. However, cholesteryl ?-glucosides were recognized by invariant natural killer T (iNKT) cells, eliciting an immune response in vitro and in vivo. Following inoculation of H. pylori harboring highly active ?CgT into iNKT cell-deficient (J?18?/?) or wild-type mice, bacterial recovery significantly increased in J?18?/? compared to wild-type mice. Moreover, cytokine production characteristic of Th1 and Th2 cells dramatically decreased in J?18?/? compared to wild-type mice. These findings demonstrate that cholesteryl ?-glucosides play critical roles in H. pylori-mediated gastric inflammation and precancerous atrophic gastritis. PMID:24312443

  18. Quercetin from shallots (Allium cepa L. var. aggregatum) is more bioavailable than its glucosides.

    PubMed

    Wiczkowski, Wieslaw; Romaszko, Jerzy; Bucinski, Adam; Szawara-Nowak, Dorota; Honke, Joanna; Zielinski, Henryk; Piskula, Mariusz K

    2008-05-01

    The lipophilic character of quercetin suggests that it can cross enterocyte membranes via simple diffusion. Therefore, it should be more bioavailable than its glucosides, which require preliminary hydrolysis or active transport for absorption. However, the published human studies show that quercetin is less bioavailable than its glucosides. Assuming that low bioavailability of quercetin aglycone provided to humans as a pure substance is the result of its low solubility in the digestive tract, we studied its bioavailability from dietary sources in which quercetin was dispersed in the food matrix. In a randomized crossover study, 9 volunteers took a single dose of either shallot flesh (99.2% quercetin glucosides and 0.8% quercetin aglycone) or dry shallot skin (83.3% quercetin aglycone and 16.7% quercetin glucosides), providing 1.4 mg quercetin per kg of body weight. Blood samples were collected before and after consumption of shallot preparations. Plasma quercetin was measured on HPLC with electrochemical detection after plasma enzymatic treatment. The maximum plasma quercetin concentration of 1.02 +/- 0.13 micromol/L was reached at 2.33 +/- 0.50 h after shallot flesh consumption compared with 3.95 +/- 0.62 micromol/L at 2.78 +/- 0.15 h after dry skin consumption. The area under the concentration-time curve after dry skin consumption was 47.23 +/- 7.53 micromol x h(-1) x L(-1) and was significantly higher than that after shallot flesh intake (22.23 +/- 2.32 micromol x h(-1) x L(-1)). When provided along with dietary sources, quercetin aglycone is more bioavailable than its glucosides in humans. Results point to the food matrix as a key factor. PMID:18424596

  19. Acylated Cyanidin 3-sophoroside-5-glucosides from the Purple Roots of Red Radish (Raphanus sativus L.) ‘Benikanmi’

    Microsoft Academic Search

    Fumi Tatsuzawa; Norio Saito; Kenjiro Toki; Koichi Shinoda; Atsushi Shigihara; Toshio Honda

    2010-01-01

    Four new acylated cyanidin glycosides were isolated from the purple root peers of Raphanus sativus L. 'Benikanmi', along with five known anthocyanins. These pigments were based on cyanidin 3-sophoroside-5- glucoside, and acylated diversely with malonic, p-coumaric, caffeic, and ferulic acids. Two pigments of these four new anthocyanins were determined to be cyanidin 3-O-(2-O-(?-glucopyranosyl)-6-O-(trans-feruloyl)-?- glucopyranoside)-5-O-(6-O-(malonyl)-?-glucopyranoside) and cyanidin 3-(2-(glucosyl)-6-(cis-p-coumaroyl)- glucoside)-5-(6-(malonyl)-glucoside) by chemical

  20. Analgesic effect of iridoid glycosides from Paederia scandens (LOUR.) MERRILL (Rubiaceae) on spared nerve injury rat model of neuropathic pain.

    PubMed

    Liu, Mei; Zhou, Lanlan; Chen, Zhiwu; Hu, Caibiao

    2012-09-01

    Iridoid glycosides of Paederia scandens (IGPS) is a major active component isolated from traditional Chinese herb P. scandens (LOUR.) MERRILL (Rubiaceae). The aim of the present study was to investigate the analgesic effect of IGPS on spared nerve injury (SNI) model of neuropathic pain. The SNI model in rats was established by complete transection of the common peroneal and tibial distal branches of the sciatic nerve, leaving the sural branch intact. The mechanical withdrawal threshold (MWT) in response to mechanical stimulation was measured by electronic von Frey filaments on day 1 before operation and on days 1, 3, 5, 7, 10, and 14 after operation, respectively. Nitric oxide synthase (NOS) activity and nitric oxide (NO) production of spinal cord were measured by spectrophotometry and its cyclic guanosine monophosphate (cGMP) content by radioimmunoassay, mRNA expression of inducible NOS (iNOS) and protein kinase G type I (PKG-I, including PKG ?? and PKG I?) of spinal cord were analyzed by RT-PCR. There was a marked mechanical hypersensitivity response observed on day 1 after operation in SNI model, which accompanied with decreased MWT. Treatment with IGPS (70, 140, 280 mg/kg) significantly alleviated SNI-induced mechanical hypersensitivity response evidenced by increased MWT; as well as markedly decreased NOS activity, NO and cGMP levels. At the same time, IGPS (70, 140, 280 mg/kg) could also inhibit mRNA expression of iNOS, PKG ?? and PKG I? in the spinal cord. The results suggested that IGPS possesses antinociceptive effect, which may be partly related to the inhibition of NO/cGMP/PKG signaling pathway in the rat SNI model of neuropathic pain. PMID:22698486

  1. (6S)-Hydroxy-3-oxo-a-ionol glucosides from Capparis spinosa fruits hsan C alis a

    E-print Network

    Rüedi, Peter

    in ionol glycosides. The a-ionol derivatives are metabolites of (+)-(S)-abscisic acid. # 2002 Elsevier-a-ionol glucosides; Abscisic acid metabolites; 1 H NMR; 13 C NMR; CD spectra; Absolute configuration 1. Introduction

  2. C-glucoside flavonoids from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br

    Microsoft Academic Search

    Pei-Cheng Zhang; Sui-Xu Xu

    2003-01-01

    Two new acetyl C-glucoside flavonoids, 8-C-?-D-(2?-O-acetyl)glucofuranosylapigenin and 3?-O-acetylvitexin, along with four known C-glucoside flavonoids, vitexin, 6?-O-acetylvitexin, 2?-O-acetylvitexin, and 2?-O-rhamnosylvitexin were isolated from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br. Their structures were elucidated by spectroscopic means and chemical evidence.

  3. New indole glucosides as biosynthetic intermediates of camptothecin from the fruits of Camptotheca acuminata.

    PubMed

    Wang, Peng; Luo, Jun; Wang, Xiao-Bing; Fan, Bo-Yi; Kong, Ling-Yi

    2015-06-01

    Six new indole glucosides (1-6) and fifteen known alkaloids (7-21) were isolated from the fruit of Camptotheca acuminata. The planar structures of 1-6 were determined on the basis of spectroscopic data analysis and their absolute configurations were established by CD. The isolated indole glucosides showed a clear biosynthetic pathway of camptothecin (7), which started from tryptamine and secologanin and was proposed by synthetic chemists previously. Particularly, compound 1 supplemented the process of the transformation from pumiloside (20) or 3-epi-pumiloside (21) to camptothecin (7). In addition, camptothecin 10-O-?-D-glucopyranoside (13) and norcamptothecin (17), synthesized in the early structural modification of 7, were first isolated from the natural resources. The new compounds 1-6 were screened for their in vitro cytotoxicity but they did not show any exciting result. PMID:25771119

  4. Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus grandifolia

    NASA Technical Reports Server (NTRS)

    Lewis, N. G.; Inciong, E. J.; Ohashi, H.; Towers, G. H.; Yamamoto, E.

    1988-01-01

    In addition to Z-coniferyl and Z-sinapyl alcohols, bark extracts of Fagus grandifolia also contain significant amounts of the glucosides, Z-coniferin, Z-isoconiferin (previously called faguside) and Z-syringin. The corresponding E-isomers of these glucosides do not accumulate to a detectable level. The accumulation of the Z-isomers suggests that either they are not lignin precursors or that they are reservoirs of monolignols for subsequent lignin biosynthesis; it is not possible to distinguish between these alternatives. The co-occurrence of Z-coniferin and Z-isoconiferin demonstrate that glucosylation of monolignols can occur at either the phenolic or the allylic hydroxyl groups.

  5. Hepatoprotective activity of twelve novel 7'-hydroxy lignan glucosides from Arctii Fructus.

    PubMed

    Yang, Ya-Nan; Huang, Xiao-Ying; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2014-09-17

    Twelve novel 7'-hydroxy lignan glucosides (1-12), including two benzofuran-type neolignans, two 8-O-4' neolignans, two dibenzylbutyrolactone lignans, and six tetrahydrofuranoid lignans, together with six known lignan glucosides (13-18), were isolated from the fruit of Arctium lappa L. (Asteraceae), commonly known as Arctii Fructus. Their structures were elucidated using spectroscopy (1D and 2D NMR, MS, IR, ORD, and UV) and on the basis of chemical evidence. The absolute configurations of compounds 1-12 were confirmed using rotating frame nuclear overhauser effect spectroscopy (ROESY), the circular dichroic (CD) exciton chirality method, and Rh2(OCOCF3)4-induced CD spectrum analysis. All of the isolated compounds were tested for hepatoprotective effects against D-galactosamine-induced cytotoxicity in HL-7702 hepatic cells. Compounds 1, 2, 7-12, and 17 showed significantly stronger hepatoprotective activity than the positive control bicyclol at a concentration of 1 × 10(-5) M. PMID:25180661

  6. Acylated cyanidin 3-sambubioside-5-glucosides in three garden plants of the Cruciferae.

    PubMed

    Tatsuzawa, Fumi; Saito, Norio; Shinoda, Koichi; Shigihara, Atsushi; Honda, Toshio

    2006-06-01

    Seven acylated cyanidin 3-sambubioside-5-glucosides were isolated from the flowers of three garden plants in the Cruciferae. Specifically, four pigments were isolated from Lobularia maritima (L.) Desv., together with a known pigment, as well as, three pigments from Lunaria annua L., and two known pigments from Cheiranthus cheiri L. These pigments were determined to be cyanidin 3-O-[2-O-((acyl-II)-(beta-d-xylopyranosyl))-6-O-(acyl-I)-beta-d-glucopyranoside]-5-O-[6-O-(acyl-III)-beta-d-glucopyranoside], in which the acyl-I group is represented by glucosyl-p-coumaric acid, p-coumaric acid and ferulic acid, acyl-II by caffeic acid and ferulic acid, and acyl-III by malonic acid, respectively. The distribution and biosynthesis of acylated cyanidin 3-sambubioside-5-glucosides are discussed according to the variations of acylation and glucosylation at their 3-sambubiose residues. PMID:16777160

  7. Benzophenone C- and O-glucosides from Cyclopia genistoides (Honeybush) inhibit mammalian ?-glucosidase.

    PubMed

    Beelders, Theresa; Brand, D Jacobus; de Beer, Dalene; Malherbe, Christiaan J; Mazibuko, Sithandiwe E; Muller, Christo J F; Joubert, Elizabeth

    2014-12-26

    An enriched fraction of an aqueous extract prepared from the aerial parts of Cyclopia genistoides Vent. yielded a new benzophenone di-C,O-glucoside, 3-C-?-d-glucopyranosyl-4-O-?-d-glucopyranosyliriflophenone (1), together with small quantities of a known benzophenone C-glucoside, 3-C-?-d-glucopyranosylmaclurin (2). The isolated compounds showed ?-glucosidase inhibitory activity against an enzyme mixture extracted from rat intestinal acetone powder. Compound 2 exhibited significantly (p < 0.05) higher inhibitory activity (54%) than 1 (43%) at 200 ?M. In vitro tests in several cell models showed that 1 and its 3-C-monoglucosylated derivative (3-C-?-d-glucopyranosyliriflophenone) were marginally effective (p ? 0.05) in increasing glucose uptake. PMID:25419864

  8. A new flavone xyloside and two new flavan-3-ol glucosides from Juniperus communis var. depressa.

    PubMed

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

    2007-01-01

    A new flavone xyloside, 1, and two new flavan-3-ol glucosides, 3 and 4, were isolated together with three known flavones, 2, 11, and 12, five known flavans, 5-9, and a known dihydrochalcone, 10, from the stems and leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral evidence. A novel flavone nucleus such as that in 1 is seldom found in nature today, and new methylcatechin glucosides 3 and 4 are also rare in nature. In addition, we investigated the inhibitory activity of individual components, i.e., 8-11, and others, that were abundantly isolated from the same plant material for the Maillard reaction. PMID:17256732

  9. Neuroprotective effect of cyanidin-3- O-glucoside anthocyanin in mice with focal cerebral ischemia

    Microsoft Academic Search

    Jiangyong Min; Seong-Woon Yu; Seung-Hoon Baek; Kavitha M. Nair; Ok-Nam Bae; Archit Bhatt; Mounzer Kassab; Muraleedharan G. Nair; Arshad Majid

    2011-01-01

    The present study sought to determine the neuroprotective effect of anthocyanin cyanidin-3-O-glucoside (CG), isolated and purified from tart cherries, against permanent middle cerebral artery occlusion (pMCAO) in mice and its potential mechanisms of neuroprotection. C57BL\\/6 mice subjected to pMCAO were treated with CG orally. Twenty-four hours after pMCAO, neurological scoring was used to evaluate functional outcome. The brains were then

  10. Stability and colour characteristics of PEF-treated cyanidin-3-glucoside during storage

    Microsoft Academic Search

    Y. Zhang; X. S. Hu; F. Chen; J. H. Wu; X. J. Liao; Z. F. Wang

    2008-01-01

    The stability and colour characteristics of PEF (pulsed electric field)-treated cyanidin-3-glucoside (Cy-3-glu) was investigated during storage at 4, 24 and 37°C. The degradation of Cy-3-glu was analyzed using a first reaction kinetics while its colour characteristics was evaluated using colour indices such as colour density (CD) and CIE L?a?b? parameters. PEF had no post-effect on the stability and colour characteristics

  11. Effect of heat\\/pressure on cyanidin-3-glucoside ethanol model solutions

    Microsoft Academic Search

    M. Corrales; R. Lindauer; P. Butz; B. Tauscher

    2008-01-01

    The stability of cyanidin-3-glucoside (Cy3gl) in 50% ethanol model solutions under heat\\/pressure treatments was investigated. Cy3gl was rapidly degraded when solutions were subjected to a heat\\/pressure treatment. The higher the pressure and the temperature used, the higher the degradation. Moreover, the degradation was increased according to increasing holding times. Parallel to the degradation of Cy3gl several hydrolytic products were formed

  12. Gastroprotective effect of cyanidin 3-glucoside on ethanol-induced gastric lesions in rats

    Microsoft Academic Search

    Chun-Ying Li; Hong-De Xu; Bing-Tian Zhao; Hyo-Ihl Chang; Hae-Ik Rhee

    2008-01-01

    This study investigated the in vivo protective effect of cyanidin 3-glucoside (C3G) against ethanol-induced gastric lesions in rats. The experimental rats were treated with 80% ethanol after pretreatment with various doses of C3G (4 and 8mg\\/kg of body weight), and the control rats received only 80% ethanol. Oral pretreatment with C3G significantly inhibited the formation of ethanol-induced gastric lesions and

  13. Dietary cyanidin 3- O -?- d -glucoside increases ex vivo oxidation resistance of serum in rats

    Microsoft Academic Search

    Takanori Tsuda; Fumihiko Horio; Toshihiko Osawa

    1998-01-01

    The effect of dietary cyanidin 3-O-?-d-glucoside (C3G), a typical anthocyanin pigment, on the generation of thiobarbituric acid reactive substances (TBARS) during\\u000a serum formation ex vivo and susceptibility of serum to further lipid peroxidation was studied in rats. Rats were fed a diet containing C3G (2 g\\/kg)\\u000a for 14 d. Feeding C3G resulted in a significant decrease in generation of TBARS

  14. Vascular mechanisms of cyanidin-3-glucoside response in streptozotocin-diabetic rats

    Microsoft Academic Search

    Sima Nasri; Mehrdad Roghani; Tourandokht Baluchnejadmojarad; Tahereh Rabani; Mahboubeh Balvardi

    2011-01-01

    Background and objective: Considering the high incidence of cardiovascular disorders in diabetes mellitus and some evidence on the antioxidant and antidiabetic potential of cyanidin-3-glucoside (C3G), this study was conducted to evaluate the possible beneficial effect of C3G administration on vascular reactivity of isolated thoracic aorta in diabetic rats and some of its underlying mechanisms. Materials and methods: Male diabetic rats

  15. Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae)

    Microsoft Academic Search

    Norio Saito; Fumi Tatsuzawa; Eri Suenaga; Kenjiro Toki; Koichi Shinoda; Atsushi Shigihara; Toshio Honda

    2008-01-01

    The structures of 11 acylated cyanidin 3-sophoroside-5-glucosides (pigments 1–11), isolated from the flowers of Iberis umbellata cultivars (Cruciferae), were elucidated by chemical and spectroscopic methods. Pigments 1–11 were acylated with malonic acid, p-coumaric acid, ferulic acid, sinapic acid and\\/or glucosylhydroxycinnamic acids.Pigments 1–11 were classified into four groups by the substitution patterns of the linear acylated residues at the 3-position of

  16. Comparative analyses of copigmentation of cyanidin 3-glucoside and cyanidin 3-sophoroside from red raspberry fruits

    Microsoft Academic Search

    Jianxia Sun; Xiamin Cao; weibin Bai; Xiaojun Liao; Xiaosong Hu

    2010-01-01

    Cyanidin 3-glucoside (Cy 3-glu) and cyanidin 3-sophoroside (Cy 3-soph) from red raspberry extracts were selected as pigments, and five phenolic acids as copigments. The influences of pH, temperature, structure of anthocyanins and copigments, and molar ratio of anthocyanins to copigments on the copigmentation effect were analyzed with a UV–Visible spectrophotometer. The reaction was thermodynamically defined in terms of ?H0, ?G0

  17. Absorption and metabolism of cyanidin 3- O-?- D-glucoside in rats

    Microsoft Academic Search

    Takanori Tsuda; Fumihiko Horio; Toshihiko Osawa

    1999-01-01

    We have clarified for the first time how cyanidin 3-O-?-D-glucoside (C3G), which is a potent antioxidant anthocyanin, is absorbed and metabolized in vivo. Rats were orally administered C3G (0.9 mmol\\/kg body weight), and C3G rapidly appeared in the plasma. However, the aglycon of C3G (cyanidin; Cy) was not detected, although it was present in the jejunum. Protocatechuic acid (PC), which

  18. Characterization and activities of S-adenosyl- l-methionine:cyanidin 3-glucoside 3?- O-methyltransferase in relation to anthocyanin accumulation in Vitis vinifera cell suspension cultures

    Microsoft Academic Search

    Christophe Bailly; François Cormier; Chi Bao Do

    1997-01-01

    A cell suspension of Vitis vinifera cv Gamay Fréaux was grown in a maintenance and an anthocyanin-promoting medium (APM). Time-course changes in anthocyanin accumulation and S-adenosyl-l-methionine:cyanidin 3-glucoside 3?-O-methyltransferase (CGMT) activity were examined throughout the growth cycle. An increase in anthocyanin accumulation mainly due to peonidin 3-glucoside and peonidin 3- p-coumaroylglucoside i.e. 3?-methylated derivatives of cyanidin 3-glucoside (Cy3G), of cells grown

  19. Differential Performance of a Specialist and Two Generalist Herbivores and Their Parasitoids on Plantago lanceolata

    E-print Network

    van Nouhuys, Saskya

    on Plantago lanceolata Joanneke H. Reudler & Arjen Biere & Jeff A. Harvey & Saskya van Nouhuys Received: 28 the effects of the concentration of the two main iridoid glycosides (IGs) in Plantago lanceolata, aucubin-diapause larval and pupal mortality on its local Finnish P. lanceolata than on Dutch genotypes. This could

  20. Isolation, identification, and color characterization of cyanidin-3-glucoside and cyanidin-3-sophoroside from red raspberry

    Microsoft Academic Search

    Yan Zhang; Xiaojun Liao; Fang Chen; Jihong Wu; Xiaosong Hu

    2008-01-01

    The major anthocyanins were isolated by Amberlite XAD-7 and Sephadex LH-20 column chromatography from the acidified, methanolic\\u000a extracts of red raspberry, their purity was over 85%. Moreover, the major anthocyanins were identified as the cyanidin-3-glucoside\\u000a (Cy-3-glu) and cyanidin-3-sophoroside (Cy-3-soph) using HPLC-PDA and HPLC\\/ESI-MS. Their UV–vis absorption spectra and color\\u000a index were also investigated. Cy-3-glu and Cy-3-soph had the similar UV–vis

  1. Pharmacokinetics and metabolism of the putative cancer chemopreventive agent cyanidin-3-glucoside in mice

    Microsoft Academic Search

    Timothy H. Marczylo; Darren Cooke; Karen Brown; William P. Steward; Andreas J. Gescher

    2009-01-01

    Purpose  Cyanidin-3-glucoside (C3G), an anthocyanin component of fruits and berries, possesses cancer chemopreventive properties in\\u000a mouse models of carcinogenesis. Its pharmacokinetics and metabolism in mice have hitherto not been studied.\\u000a \\u000a \\u000a \\u000a Methods  C57BL6J mice received C3G by either gavage at 500 mg\\/kg or tail vein injection at 1 mg\\/kg. Blood, urine, bile and heart, lung,\\u000a kidney, liver, prostate, brain and gastrointestinal (gi) mucosal tissues were

  2. Purification and anti-tumour activity of cyanidin-3- O-glucoside from Chinese bayberry fruit

    Microsoft Academic Search

    Chongde Sun; Yixiong Zheng; Qingjun Chen; Xianglian Tang; Ming Jiang; Jiukai Zhang; Xian Li; Kunsong Chen

    Chinese bayberry (Myrica rubra Sieb. & Zucc.) is a rich source of cyanidin-3-O-glucoside (C3G). Purification of C3G was established by using high-speed counter-current chromatography (HSCCC) at 520nm. The optimised flow rate was 2ml\\/min and rotational speed was 850rpm, and n-butanol–methyl tertiary butyl ether–acetonitrile–trifluoroacetic acid–water (30:20:40:1:100, v\\/v\\/v\\/v\\/v) solvent showed the highest partition coefficient (K=1.50) to purify C3G. Different HSCCC fractions showed

  3. Antioxidant properties and structural analysis of phenolic glucosides from bark of Populus ussuriensis Kom

    Microsoft Academic Search

    Chuan-Ling Si; Jie Xu; Jin-Kyu Kim; Young-Soo Bae; Peng-Tao Liu; Zhong Liu

    2011-01-01

    The methanol (MeOH) extract of Populus ussuriensis Kom. bark was analyzed for antioxidant assessing by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging potential. Among\\u000a fractions using several solvents, the ethyl acetate (EtOAc) soluble fraction, which showed strong antioxidant activity (IC50 2.02 ± 0.01 ?g\\/ml), was further purified by Thin layer chromatography (TLC) guided Sephadex LH-20 column chromatography.\\u000a Three known phenolic glucosides, picein (I), salicortin (II), grandidentatin

  4. Quercetin glucosides inhibit glucose uptake into brush-border-membrane vesicles of porcine jejunum

    Microsoft Academic Search

    Rainer Cermak; Sandra Landgraf; Siegfried Wolffram

    2004-01-01

    Recent experimental data point to an interaction of dietary flavonol monoglucosides with the intestinal Na-dependent glucose transporter 1 (SGLT1). To investigate this interaction in more detail, we performed experiments with SGLT1-containing brush-border-membrane ves- icles (BBMV) from pig jejunum. The flavonol quercetin-3-O-glucoside (Q3G) concentration-dependently inhibited Na-dependent uptake of radioactively labelled D-glucose into BBMV. Uptake of L-leucine was not inhibited by Q3G,

  5. Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts

    Microsoft Academic Search

    Cristiano Soleo Funari; Thais Gaban Passalacqua; Daniel Rinaldo; Assunta Napolitano; Michela Festa; Anna Capasso; Sonia Piacente; Cosimo Pizza; Maria Claudia Marx Young; Giselda Durigan; Dulce Helena Siqueira Silva

    2011-01-01

    Four interconverting flavanone glycosides [(2R)- and (2S)-3?,4?,5,6-tetrahydroxyflavanone 7-O-?-d-glucopyranoside, and (2R)- and (2S)-3?,4?,5,8-tetrahydroxyflavanone 7-O-?-d-glucopyranoside], in addition to eight known flavonoids [naringenin, asebogenin, sakuranetin, 6-hydroxyluteolin 7-O-?-d-glucoside, (2R)- and (2S)-eriodictyol 7-O-?-d-glucopyranoside, aromadendrin and phloretin], three phenylpropanoid glycosides [forsythoside B, alyssonoside and verbascoside] and the epoxylignan lariciresinol 4?-O-?-d-glucopyranoside were isolated and identified in the EtOH extract of the aerial parts of Lippia salviaefolia Cham.

  6. New CuCl2-induced glucoside esters and other constituents from Portucala oleracea.

    PubMed

    Wu, Bin; Yu, Liyan; Wu, Xiaodan; Chen, Jianbo

    2012-04-01

    Two new glucoside esters 1 and 2 were produced as stress metabolites in the fresh leaves of Portulaca oleracea, in response to abiotic stress elicitation by CuCl(2). A new sugar ester (3) and two known compounds (4 and 5) were also isolated. Their structures were established by spectroscopic means. The antioxidative activities of stress metabolites and the related isolates were evaluated by DPPH assay. The results showed that new stress-driven adducts of monolignans and monoterpenes with a glucose bridge exhibited much stronger antioxidative activities than other compounds. PMID:22361155

  7. Acylated Pelargonidin 3-sambubioside-5-glucosides from the Red-purple Flowers of Lobularia maritima

    Microsoft Academic Search

    Fumi Tatsuzawa; Rie Usuki; Kenjiro Toki; Norio Saito; Koichi Shinoda; Atsushi Shigihara; Toshio Honda

    2010-01-01

    Six acylated pelargonidin 3-O-sambubioside-5-O-glucosides were isolated from red-purple flowers of Lobularia maritima (L.) Desv. 'Easter Bonnet Deep Rose'. These pigments were determined by chemical and spectroscopic methods to be pelargonidin 3-O-(2-O-(2-O-(acyl-II)-?-xylopyranosyl)-6-O-(acyl-I)-?-glucopyranoside)-5-O-?- glucopyranoside, in which the acyl-I group was replaced by 4-O-glucosyl-p-coumaric acid, p-coumaric acid or ferulic acid, and acyl-II by caffeic acid or ferulic acid, respectively. In comparison with the

  8. Acylated cyanidin 3-sambubioside-5-glucosides in three garden plants of the Cruciferae

    Microsoft Academic Search

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

    2006-01-01

    Seven acylated cyanidin 3-sambubioside-5-glucosides were isolated from the flowers of three garden plants in the Cruciferae. Specifically, four pigments were isolated from Lobularia maritima (L.) Desv., together with a known pigment, as well as, three pigments from Lunaria annua L., and two known pigments from Cheiranthus cheiri L. These pigments were determined to be cyanidin 3-O-[2-O-((acyl-II)-(?-d-xylopyranosyl))-6-O-(acyl-I)-?-d-glucopyranoside]-5-O-[6-O-(acyl-III)-?-d-glucopyranoside], in which the acyl-I

  9. A new diterpenoid glucoside and two new diterpenoids from the fruit of Vitex agnus-castus.

    PubMed

    Ono, Masateru; Eguchi, Keisuke; Konoshita, Masatarou; Furusawa, Chisato; Sakamoto, Junich; Yasuda, Shin; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Yoshimitsu, Hitoshi; Nohara, Toshihiro

    2011-01-01

    A new labdane-type diterpenoid glucoside and two new labdane-type diterpenoids were isolated from the fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with 14 known compounds comprising seven labdane-type diterpenoids, one halimane-type diterpenoid, two oleanane-type triterpenoids, two ursane-type triterpenoids, one aromadendrane-type sesquiterpenoid, and one flavonoid. Their structures were characterized on the basis of spectroscopic data as well as chemical evidence. Furthermore, the antioxidative activities of the flavonoid were evaluated using five different analyses. PMID:21372425

  10. 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

  11. Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

    PubMed Central

    Mebrahtu, Fanuel M; Manana, Mandlenkosi M; Madumo, Kagiso; Sokamisa, Mokela S

    2015-01-01

    Summary 1-C and 2-C-branched carbohydrates are present as substructures in a number of biologically important compounds. Although the synthesis of such carbohydrate derivatives is extensively studied, the synthesis of 1,2-cis-2-C-branched C-, S-, and N-glycosides is less explored. In this article a synthetic strategy for the synthesis of 1,2-cis-2-C-branched-aryl-C-glucosides is reported via a hydrogenolytic desulfurization of suitably orientated carbohydrate based hemithioacetals. 1,2-cis-2-Hydroxymethyl and 2-carbaldehyde of aryl-C-glucosides have been synthesized using the current strategy in very good yields. The 2-carbaldehyde-aryl-C-glucosides have been identified as suitable substrates for the stereospecific preparation of 2,3-unsaturated-aryl-C-glycosides (Ferrier products).

  12. Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes

    PubMed Central

    2013-01-01

    Inhibition of the renal sodium glucose cotransporter (SGLT) increases urinary glucose excretion (UGE) and thus reduces blood glucose levels during hyperglycemia. To explore the potential of new antihyperglycemic agents, we synthesized and determined the human SGLT2 (hSGLT2) inhibitory potential of novel substituted 3-benzylindole-N-glucosides 6. Optimization of 6 resulted in the discovery of 3-(4-cyclopropylbenzyl)-4-fluoroindole-N-glucoside 6a-4 (TA-1887), a highly potent and selective hSGLT2 inhibitor, with pronounced antihyperglycemic effects in high-fat diet-fed KK (HF-KK) mice. Our results suggest the potential of indole-N-glucosides as novel antihyperglycemic agents through inhibition of renal SGLT2. PMID:24900773

  13. Effects on Liver Lipid Metabolism of the Naturally Occurring Dietary Flavone Luteolin-7-glucoside

    PubMed Central

    Sá, Carla; Oliveira, Ana Rita; Machado, Cátia; Azevedo, Marisa; Pereira-Wilson, Cristina

    2015-01-01

    Disruptions in whole-body lipid metabolism can lead to the onset of several pathologies such as nonalcoholic fatty liver disease (NAFLD) and cardiovascular diseases (CVDs). The present study aimed at elucidating the molecular mechanisms behind the lipid-lowering effects of the flavone luteolin-7-glucoside (L7G) which we previously showed to improve plasma lipid profile in rats. L7G is abundant in plant foods of Mediterranean diet such as aromatic plants used as herbs. Results show that dietary supplementation with L7G for one week induced the expression of peroxisome proliferator-activated receptor-alpha (PPAR-?) and of its target gene carnitine palmitoyl transferase 1 (CPT-1) in rat liver. L7G showed a tendency to decrease the hepatic expression of sterol regulatory element-binding protein-1 (SREBP-1), without affecting fatty acid synthase (FAS) protein levels. Although SREBP-2 and LDLr mRNA levels did not change, the expression of HMG CoA reductase (HMGCR) was significantly repressed by L7G. L7G also inhibited this enzyme's in vitro activity in a dose dependent manner, but only at high and not physiologically relevant concentrations. These results add new evidence that the flavone luteolin-7-glucoside may help in preventing metabolic diseases and clarify the mechanisms underlying the beneficial health effects of diets rich in fruits and vegetables.

  14. Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia.

    PubMed

    Sekhon-Loodu, Satvir; Ziaullah, Ziaullah; Rupasinghe, H P Vasantha; Wang, Yanwen; Kulka, Marianna; Shahidi, Fereidoon

    2015-08-01

    Quercetin, a major flavonol, present abundantly in apples and onions, is widely studied for ameliorating metabolic syndrome abnormalities. However, quercetin is mainly present in plant food in the form of quercetin glycosides and has been reported for poor gastrointestinal absorption. The present study was designed with the purpose of imparting a lipophilic property to quercetin-3-O-glucoside (QG) by its acylation with eicosapentaenoic acid (EPA) and to study the influence of eicosapentaenoic acid ester of quercetin-3-O-glucoside (QE) on hyperlipidemia and inflammation in vivo and in vitro. QE was more effective in reducing the production of tumor necrosis factor-alpha (TNF-?), prostaglandin 2 (PGE2), cyclo-oxygenase (COX)-2 levels and nuclear expression of nuclear factor-kappa B (NF-?B) compared to the parent compounds (QG and EPA) and commercial drugs, after lipopolysaccharides (LPS) induced inflammation in THP-1 derived macrophages. Serum high-density lipoprotein (HDL)-cholesterol was significantly higher and hepatic total cholesterol concentration was lower in the rats fed high-fat diet supplemented with QE, compared to the high-fat diet with inflammation (HFL). The serum concentrations of C-reactive protein (CRP), interleukin (IL)-6, and interferon-gamma (IFN-?) were significantly lower in QE treatment group than HFL group. EPA conjugated flavonol, QE, had significant anti-inflammatory and hypolipidemic properties and may be effective for the treatment of obesity-related disorders. PMID:26165697

  15. Isoarnottinin 4'-glucoside, a glycosylated coumarin from Prangos uloptera, with biological activity.

    PubMed

    Razavi, Seyed Mehdi; Zarrini, Gholamreza; Rad, Farah Gholami

    2011-01-01

    Coumarins are a well-known group of natural products distributed in the plant kingdom especially in the family Apiaceae with various biological activities. Isoarnottinin 4'-glucoside is a simple glycosylated coumarin found previously in a few genera of Apiaceae, and its biological activities have not been previously described in details. In the present paper, the compound was isolated from Prangos uloptera (Apiaceae) leaves using HPLC techniques. Antimicrobial, phytotoxic and cytotoxic activities of the compound were evaluated by disk diffusion, lettuce assay and MTT method. Our results indicated that the compound has high antibacterial effect against Erwinia carotovora, a common plant pathogen with MIC value of 100 microg/mL. The compound also exhibited significant phytotoxic activity against lettuce and modest cytotoxic activity against HeLa cell line with IC50 of 0 .84 mg/mL. It could be concluded that isoamottinin 4'-glucoside may play phytoalexin or allelopathic role for plant and may be a candidate for an antibacterial agent or a bioherbicide. PMID:21717896

  16. All eight possible mono-beta-D-glucosides of validoxylamine A. I. Preparation and structure determination.

    PubMed

    Asano, N; Kameda, Y; Matsui, K

    1991-12-01

    Validamycin A is the major and most active compound among the validamycin complex. Since the site of beta-glucosidic attachment to validoxylamine A (1) was expected to affect the activity against the pathogenic fungus, Rhizoctonia solani, all eight possible mono-beta-D-glucosides of 1 were prepared. 2-O-, 4-O-, 4'-O-, and 7'-O-beta-D-glucopyranosylvalidoxylamine A (2, 4, 6 and 9, respectively) were prepared by microbial beta-glycosylation of 1 with strains of Rhodotorula sp. 7-O- and 6'-O-beta-D-glucopyranosylvalidoxylamine A (5a and 8a, respectively) were prepared semisynthetically through microbial formation of 7-O-beta-D-glucopyranosylvalidamine (10), oxidation of the primary amine of 10 to a ketone, and coupling of the ketone derivative with valienamine, and through microbial formation of 6-O-beta-D-glucopyranosylvalienamine (11), and coupling of 11 with (2R)-(2,4/3,5)-2,3,4-trihydroxy-5-hydroxymethylcyclohexanone (12), respectively. 3-O- and 5'-O-beta-D-glucopyranosylvalidoxylamine A (3a and 7a, respectively) were chemically synthesized. PMID:1778791

  17. Temporal synthesis and radiolabelling of the sorghum 3-deoxyanthocyanidin phytoalexins and the anthocyanin, cyanidin 3-dimalonyl glucoside

    Microsoft Academic Search

    PHILLIP S. W HARTON; RALPH L. N ICHOLSON

    summary Sorghum (Sorghum bicolor) synthesizes a complex mixture of 3-deoxyanthocyanidin phytoalexins in response to inoculation with the non-pathogenic fungus Bipolaris maydis. The anthocyanin cyanidin 3-dimalonyl glucoside, is also synthesized naturally in response to light. To determine the order and time of appearance of these compounds, etiolated sorghum mesocotyls were inoculated with B. maydis and tissue extracts were analysed by photodiode

  18. Cyanidin 3-glucoside ameliorates hyperglycemia and insulin sensitivity due to downregulation of retinol binding protein 4 expression in diabetic mice

    Microsoft Academic Search

    Rie Sasaki; Natsumi Nishimura; Hiromi Hoshino; Yasuka Isa; Maho Kadowaki; Takahito Ichi; Akihito Tanaka; Shin Nishiumi; Itsuko Fukuda; Hitoshi Ashida; Fumihiko Horio; Takanori Tsuda

    2007-01-01

    Adipocyte dysfunction is strongly associated with the development of obesity and insulin resistance. It is accepted that the regulation of adipocytokine expression is one of the most important targets for the prevention of obesity and improvement of insulin sensitivity. In this study, we have demonstrated that anthocyanin (cyanidin 3-glucoside; C3G) which is a pigment widespread in the plant kingdom, ameliorates

  19. In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer

    Microsoft Academic Search

    Jeanelle Boyer; Dan Brown; Rui Hai Liu

    2005-01-01

    BACKGROUND: Quercetin and quercetin glycosides are widely consumed flavonoids found in many fruits and vegetables. These compounds have a wide range of potential health benefits, and understanding the bioavailability of flavonoids from foods is becoming increasingly important. METHODS: This study combined an in vitro digestion, a lactase treatment and the Caco-2 cell model to examine quercetin and quercetin glucoside uptake

  20. Clarification of Reconstituted Frozen Orange Juice Concentrate by Continuous Flow Centrifugation for Limonin Glucoside Solid Phase Extraction

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The clarification of reconstituted frozen orange juice concentrate by continuous-flow centrifugation in preparation to being applied to a solid phase extraction column for the isolation of limonin glucoside has been evaluated. Clarification experiments spanning over three different flow rates (325,...

  1. Ptaquiloside Z, a new toxic unstable sesquiterpene glucoside from the neotropical bracken fern pteridium aquilinum var. caudatum

    Microsoft Academic Search

    Uvidelio Francisco Castillo; Makoto Ojika; Miguel Alonso-Amelot; Youji Sakagami

    1998-01-01

    Reversed-phase HPLC fractionation, monitored by brine shrimp bioassay, led to the isolation of a new illudane-type sesquiterpene glucoside, ptaquiloside Z (2), as well as the known bracken carcinogen ptaquiloside (1), from a bioactive aqueous extract of the neotropical bracken fern Pteridium aquilinum var. caudatum (Pteridaceae). The structure of ptaquiloside Z (2) was confirmed by spectroscopic analyses and chemical degradation. Both

  2. Cyanogenic and non-cyanogenic pyridone glucosides from Acalypha indica (Euphorbiaceae).

    PubMed

    Hungeling, Monika; Lechtenberg, Matthias; Fronczek, Frank R; Nahrstedt, Adolf

    2009-01-01

    Seven cyanopyridone derivatives and one corresponding seco compound have been isolated from a methanolic extract of the inflorescences and leaves of Acalypha indica L. (Euphorbiaceae). The absolute configuration of the main cyanogenic glucoside acalyphin, (-)-(5R,6S)-5-cyano-5-beta-d-glucopyranosyloxy-6-hydroxy-4-methoxy-1-methyl-2(5,6-dihydro)-pyridone, was deduced from an X-ray crystallographic study. In addition, the 6R-epimer of acalyphin, epiacalyphin, and the corresponding pair of N-demethyl derivatives were isolated. The corresponding amide of acalyphin and a 1',2'-glucosyl-fused epiacalyphin amide were isolated from air-dried material. Structural elucidation was performed by means of (1)H and (13)C NMR-spectra, chiroptical methods such as CD-spectroscopy and optical rotation. Two further corresponding derivatives, an aromatized compound and an open-chain structure, were isolated from the aqueous phase. PMID:19157466

  3. Three spirostanol saponins and a flavane-O-glucoside from the fresh rhizomes of Tupistra chinensis.

    PubMed

    Xiao, Yan-Hua; Yin, Hai-Long; Chen, Li; Tian, Yin; Liu, Shi-Jun; Zhang, Guang-Jie; Chen, Heng-Wen; Jin, Hong; Li, Bin; Dong, Jun-Xing

    2015-04-01

    Four new compounds, including three new spirostanol saponins [tupistroside G-I (1-3)] and a new flavane-O-glucoside [tupichiside A (4)], together with ten known compounds, were isolated from the fresh rhizomes of Tupistra chinensis. The structures of the new compounds were elucidated by spectroscopic analysis and chemical evidence. All compounds were tested in vitro for their cytotoxic activities against the Human LoVo and BGC-823 cell lines, and six of them were found to possess potent cytotoxicity. Compounds 2, 8 and 9 showed significant cytotoxicity against the tested tumor cell lines with IC50 values ranging from 0.2 to 0.9?M. PMID:25707589

  4. Structure and cytotoxic activity of enzymatic hydrolysis products of secoiridoid glucosides, isoligustroside and isooleuropein.

    PubMed

    Kikuchi, Masafumi; Yaoita, Yasunori; Mano, Nariyasu; Kikuchi, Masao

    2011-04-01

    Hydrolysis of isoligustroside (1) and isooleuropein (2), secoiridoid glucosides, in the presence of ?-glucosidase provided 2-(4-hydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (3) and 2-(3,4-dihydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (4), respectively. The structures of 3 and 4 were elucidated on the basis of extensive spectral analyses, including 2D-NMR experiments. Compounds 3 and 4 were found to be new rearrangement products of the aglycones of 1 and 2. The cytotoxic activities of 3 and 4 were evaluated using a disease-oriented panel of 39 human cancer cell lines and showed moderate cytotoxic activity for 4, while 3 exhibited weaker activity compared to that of 4. PMID:21480510

  5. Occurrence of Deoxynivalenol and Deoxynivalenol-3-glucoside in Hard Red Spring Wheat Grown in the USA

    PubMed Central

    Simsek, Senay; Ovando-Martínez, Maribel; Ozsisli, Bahri; Whitney, Kristin; Ohm, Jae-Bom

    2013-01-01

    Deoxynivalenol (DON) is a mycotoxin found in wheat that is infected with Fusarium fungus. DON may also be converted to a type of “masked mycotoxin”, named deoxynivalenol-3-glucoside (D3G), as a result of detoxification of the plant. In this study, DON and D3G were measured using gas chromatographic (GC) and liquid chromatography-mass spectrometry (LC-MS) in wheat samples collected during 2011 and 2012 in the USA. Results indicate that the growing region had a significant effect on the DON and D3G (p < 0.0001). There was a positive correlation between both methods (GC and LC-MS) used for determination of DON content. DON showed a significant and positive correlation with D3G during 2011. Overall, DON production had an effect on D3G content and kernel damage, and was dependent on environmental conditions during Fusarium infection. PMID:24351720

  6. Antioxidant activities of three dihydrochalcone glucosides from leaves of Lithocarpus pachyphyllus.

    PubMed

    Yang, Wei-Min; Liu, Ji-Kai; Qin, Xiang-Dong; Wu, Wan-Lin; Chen, Zhi-He

    2004-01-01

    In vitro antioxidant activities of three sweet dihydrochalcone glucosides from the leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae), trilobatin 2"-acetate (1), phloridzin (2) and trilobatin (3), were investigated. The IC50 (50% inhibitory concentration) values for compounds 1-3 of lipid peroxidation in rat liver homogenate were 261, 28, 88 microM, respectively. Compounds 1-3 increased superoxide dismutase (SOD) activity with EC50 (50% effective concentration) values of 575, 167, 128 microM, and glutathione peroxidase (GSH-Px) activity with EC50 values of 717, 347, 129 microM, respectively, and showed only weak DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity. PMID:15813365

  7. Synthesis and antimicrobial activity of 6-triazolo-6-deoxy eugenol glucosides.

    PubMed

    de Souza, Thiago Belarmino; Raimundo, Paulo Otávio Botelho; Andrade, Saulo Fernandes; Hipólito, Taciane Maira Magalhães; Silva, Naiara Chaves; Dias, Amanda Latercia Tranches; Ikegaki, Masaharu; Rocha, Raissa Prado; Coelho, Luiz Felipe Leomil; Veloso, Marcia Paranho; Carvalho, Diogo Teixeira; Dias, Danielle Ferreira

    2015-06-17

    A new series of 1,2,3-triazole eugenol glucosides were synthesized. The new compound structures were confirmed by MS, (1)H NMR and (13)C NMR. All of the synthesized compounds were screened for antimicrobial and cytotoxic activity. Five compounds exerted significant activity against the Gram-negative bacteria Salmonella typhimurium with low IC50 values (49.73-68.53 ??), and seven compounds were active against the Gram-positive bacteria Micrococcus luteus (42.89-210.94 ?M). In vitro cytotoxicity on mouse spleen cells was also evaluated. One compound bearing a phenyl substituent at the triazole ring showed good activity against Salmonella typhimurium (49.73 ?M) and low toxicity to normal cells (CC50=157.83 ?M). Thus, the compounds herein can be considered for further modification for improving their antibacterial activity or obtaining novel antibacterial drug candidates. PMID:25933362

  8. New fatty acid, aromatic ester and monoterpenic benzyl glucoside from the fruits of Withania coagulans Dunal.

    PubMed

    Ali, Abuzer; Jameel, Mohammad; Ali, Mohammed

    2015-07-01

    The fruits of Withania coagulans Dunal (family: Solanaceae) are sweet, sedative, emetic, alterative and diuretic; used to treat asthma, biliousness, strangury, wounds, dyspepsia, flatulent colic, liver complaints and intestinal infections in the indigenous system of medicine. Phytochemical investigation of the methanolic extract of W. coagulans fruits led to the isolation of a new fatty acid, an aromatic ester and a monoterpenic benzyl glucoside characterised as n-octatriacont-17-enoic acid (3), geranilan-10-olyl dihydrocinnamoate (4) and geranilan-8-oic acid-10-olyl salicyloxy-2-O-?-d-glucofuranosyl-(6??1?)-O-?-d-glucofuranosyl-6?-n-octadec-9?',11?'-dienoate (5) along with two known fatty acids, n-dotriacont-21-enoic acid (1) and n-tetratriacontanoic acid (2). The structures of isolated phytoconstituents were established on the basis of 1D and 2D NMR, FT-IR, UV, and MS data and chemical means. PMID:25674818

  9. Molecular cloning and characterization of genistein 4'-O-glucoside specific glycosyltransferase from Bacopa monniera.

    PubMed

    Ruby; Santosh Kumar, R J; Vishwakarma, Rishi K; Singh, Somesh; Khan, Bashir M

    2014-07-01

    Health related benefits of isoflavones such as genistein are well known. Glycosylation of genistein yields different glycosides like genistein 7-O-glycoside (genistin) and genistein 4'-O-glycoside (sophoricoside). This is the first report on isolation, cloning and functional characterization of a glycosyltransferase specific for genistein 4'-O-glucoside from Bacopa monniera, an important Indian medicinal herb. The glycosyltransferase from B. monniera (UGT74W1) showed 49% identity at amino acid level with the glycosyltransferases from Lycium barbarum. The UGT74W1 sequence contained all the conserved motifs present in plant glycosyltransferases. UGT74W1 was cloned in pET-30b (+) expression vector and transformed into E. coli. The molecular mass of over expressed protein was found to be around 52 kDa. Functional characterization of the enzyme was performed using different substrates. Product analysis was done using LC-MS and HPLC, which confirmed its specificity for genistein 4'-O-glucoside. Immuno-localization studies of the UGT74W1 showed its localization in the vascular bundle. Spatio-temporal expression studies under normal and stressed conditions were also performed. The control B. monniera plant showed maximum expression of UGT74W1 in leaves followed by roots and stem. Salicylic acid treatment causes almost tenfold increase in UGT74W1 expression in roots, while leaves and stem showed decrease in expression. Since salicylic acid is generated at the time of injury or wound caused by pathogens, this increase in UGT74W1 expression under salicylic acid stress might point towards its role in defense mechanism. PMID:24664316

  10. Biosynthesis of cyanogenic glucosides in Triglochin maritima and the involvement of cytochrome P450 enzymes.

    PubMed

    Nielsen, J S; Moller, B L

    1999-08-01

    The biosynthesis of the two cyanogenic glucosides, taxiphyllin and triglochinin, in Triglochin maritima (seaside arrow grass) has been studied using undialyzed microsomal preparations from flowers and fruits. Tyrosine was converted to p-hydroxymandelonitrile with V(max) and K(m) values of 36 nmol mg(-1) g(-1) fresh weight and 0.14 mM, respectively. p-Hydroxyphenylacetaldoxime and p-hydroxyphenylacetonitrile accumulated as intermediates in the reaction mixtures. Using radiolabeled tyrosine as substrate, the radiolabel was easily trapped in p-hydroxyphenylacetaldoxime and p-hydroxyphenylacetonitrile when these were added as unlabeled compounds. p-Hydroxyphenylacetaldoxime was the only product obtained using microsomes prepared from green leaves or dialyzed microsomes prepared from flowers and fruits. These data contrast earlier reports (Hösel and Nahrstedt, Arch. Biochem. Biophys. 203, 753-757, 1980; and Cutler et al., J. Biol. Chem. 256, 4253-4258, 1981) where p-hydroxyphenylacetaldoxime was found not to accumulate. All steps in the conversion of tyrosine to p-hydroxymandelonitrile were found to be catalyzed by cytochrome P450 enzymes as documented by photoreversible carbon monoxide inhibition, inhibition by antibodies toward NADPH-cytochrome P450 oxidoreductase, and by cytochrome P450 inhibitors. We hypothesize that cyanogenic glucoside synthesis in T. maritima is catalyzed by multifunctional cytochrome P450 enzymes similar to CYP79A1 and CYP71E1 in Sorghum bicolor except that the homolog to CYP71E1 in T. maritima exhibits a less tight binding of p-hydroxyphenylacetonitrile, thus permitting the release of this intermediate and its conversion into triglochinin. PMID:10415119

  11. Protective effect of iridoid glycosides from Paederia scandens (LOUR.) MERRILL (Rubiaceae) on uric acid nephropathy rats induced by yeast and potassium oxonate.

    PubMed

    Hou, Shi-xiang; Zhu, Wen-jing; Pang, Ming-qun; Jeffry, Joseph; Zhou, Lan-lan

    2014-02-01

    Iridoid glycosides of Paederia scandens (IGPS) are an active component isolated from Chinese herb P. scandens (LOUR.) MERRILL (Rubiaceae). Uric acid nephropathy (UAN) is caused by excessive uric acid, which results in damage of kidney tissue via urate crystals deposition in the kidneys. This study aimed to investigate the protective effects of IGPS on UAN in rats induced by yeast and potassium oxonate. Treatment groups received different doses of IGPS and allopurinol (AP) daily for 35 days respectively. The results showed that treatment with IGPS significantly prevented the increases of uric acid in serum and the elevation of systolic blood pressure (SBP), attenuated renal tissue injury, improved renal function and reserved the biological activity of NOS-1. IGPS also inhibited the biological activity of TNF-? and TGF-?1, and suppressed the mRNA expressions of TNF-? and TGF-?1 in renal tissue. Taken together, the present and our previous findings suggest that IGPS exerts protective effects against kidney damage in UAN rats through its uric acid-lowering, anti-inflammatory and immunomodulatory properties. Furthermore, decreasing SBP by up regulation of NOS-1 expression and down regulation of TNF-? and TGF-?1 expression are involved in the effect of IGPS on high uric acid-induced nephropathy. PMID:24287205

  12. Qualitative and Quantitative Analysis of Phenolic Acids, Flavonoids and Iridoid Glycosides in Yinhua Kanggan Tablet by UPLC-QqQ-MS/MS.

    PubMed

    Lin, Yu; Xu, Wen; Huang, Mingqing; Xu, Wei; Li, Huang; Ye, Miao; Zhang, Xun; Chu, Kedan

    2015-01-01

    A simple, rapid and specific ultra-performance liquid chromatography-triple quadrupole mass spectrometry method was developed for the analysis of 29 bioactive components (10 phenolic acids, 16 flavonoids, and three iridoid glycosides) in Yinhua Kanggan tablet (YHKGT), a herbal prescription used for treating upper respiratory infections, fevers, coughs and pharyngalgia. The separation was successfully achieved using a Waters Cortecs UPLC C18 column (50 × 2.1 mm, 1.6 ?m) and gradient elution with water-0.1% formic acid and acetonitrile. Polarity switching mode was used in the optimization of multiple reaction monitoring conditions. The analytical method was validated for linearity, precision and accuracy. Calibration curves for the 29 marker compounds showed good linear regression (r > 0.9982). The limits of detection (LOD) and limits of quantification (LOQ) for the 29 analytes were in the range of 0.03-4.99 ng/mL and 0.16-14.87 ng/mL, respectively. The relative standard deviation (RSD) values of intra-day precision, inter-day precision, repeatability, and stability were less than 2.79%, 4.87%, 4.18% and 4.71%, respectively. The recoveries of the 29 marker compounds were in the range of 94.67%-104.78% (RSD ? 4.72%). These results have shown that this developed method was efficient for the quality evaluation of YHKGT. PMID:26151117

  13. Anti-allergic effects of enzymatically modified isoquercitrin (?-oligoglucosyl quercetin 3-O-glucoside), quercetin 3-O-glucoside, ?-oligoglucosyl rutin, and quercetin, when administered orally to mice.

    PubMed

    Makino, Toshiaki; Kanemaru, Misaki; Okuyama, Shuji; Shimizu, Ryosuke; Tanaka, Hisashi; Mizukami, Hajime

    2013-10-01

    Quercetin, a flavonol distributed widely in edible and medicinal plants, has beneficial biological activities in vitro. However, the low water solubility of quercetin limits its bioavailability to exhibit activity in vivo. We evaluated the anti-allergic effects of quercetin, quercetin 3-O-glucoside (isoquercitrin, IQC), ?-oligoglucosyl rutin (?OR), and enzymatically modified isoquercitrin (?-oligoglucosyl isoquercitrin; EMIQ) in the murine ear passive cutaneous anaphylaxis (PCA) reaction using ovalbumin as an antigen. The substances to be tested were dissolved or suspended in water, and administered orally to mice (4 mmol 10 ml?¹ kg?¹). EMIQ exhibited a significant inhibitory effect on the PCA reaction. We detected 600 ?M IQC and 95.1 ?M Q3Glcn in the plasma of mice 30 min after EMIQ treatment, suggesting that IQC and Q3Glcn might be the genuine active compounds mediating the anti-allergic effects of EMIQ. Oral treatments of quercetin and ?OR at this dosage exhibited no anti-allergic effect, and IQC showed less effect than EMIQ. Since IQC and quercetin cannot completely dissolve in water at this concentration, the water solubilities of these substances might affect their biological activities. ?OR dissolved well in water at the concentration used but plasma concentrations of quercetin metabolites in mice orally treated with ?OR were low, suggesting that ?OR might not be converted to IQC or quercetin by the enzymes in small intestine and thus not exhibit any activity. Glycosyl conjugation of quercetin with specific sugar motifs is an effective strategy to improve the biological activity of quercetin in vivo. PMID:23494818

  14. Synthesis and Biologic Evaluation of 11C-Methyl- D-Glucoside, a Tracer of the Sodium-Dependent Glucose Transporters

    Microsoft Academic Search

    Guy M. Bormans; Griet Van Oosterwyck; Tjibbe J. de Groot; Maike Veyhl; Luc Mortelmans; Alfons M. Verbruggen; Hermann Koepsell

    This study aimed to synthesize and to evaluate the biologic characteristics of 11C labeled methyl-D-glucoside, a nonme- tabolizable tracer that is selectively transported by sodium- dependent glucose transporters (SGLTs). Methods: 11C-Meth- yl-D-glucoside was prepared by methylation of glucose with 11C-methyl triflate and was obtained as a mixture of anomers that were separated with high-performance liquid chromatog- raphy. The biodistribution of

  15. AGT1, encoding an alpha-glucoside transporter involved in uptake and intracellular accumulation of trehalose in Saccharomyces cerevisiae.

    PubMed

    Plourde-Owobi, L; Durner, S; Parrou, J L; Wieczorke, R; Goma, G; François, J

    1999-06-01

    The trehalose content in Saccharomyces cerevisiae can be significantly manipulated by including trehalose at an appropriate level in the growth medium. Its uptake is largely dependent on the expression of AGT1, which encodes an alpha-glucoside transporter. The trehalose found in a tps1 mutant of trehalose synthase may therefore largely reflect its uptake from the enriched medium that was employed. PMID:10368160

  16. Protective effects of cyanidin-3- O-glucoside from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure

    Microsoft Academic Search

    Ivana Serraino; Laura Dugo; Paola Dugo; Luigi Mondello; Emanuela Mazzon; Giovanni Dugo; Achille Patrizio Caputi; Salvatore Cuzzocrea

    2003-01-01

    Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants.The content of blackberry (Rubus species) juice was investigated by HPLC\\/ESI\\/MS using narrow bore HPLC columns. Using this method we demonstrated that cyanidin-3-O-glucoside represents about 80% of the total anthocyanin

  17. Absorption and metabolism of cyanidin-3-glucoside and cyanidin-3-rutinoside extracted from wild mulberry ( Morus nigra L.) in rats

    Microsoft Academic Search

    Neuza Mariko Aymoto Hassimotto; Maria Inés Genovese; Franco Maria Lajolo

    2008-01-01

    The mechanism of uptake of anthocyanins (as well as the type) from food in the intestine is not clear. Anthocyanin-rich extract from wild mulberry, composed of cyanidin-3-glucoside (79%) and cyanidin-3-rutinoside (cy-3-rut) (19%), was orally administered to Wistar rats, and their concentrations were determined in plasma, kidney, and the gastrointestinal (GI) tract. The 2 glycosylated forms showed maximum concentration at 15

  18. Protective Effects of Dietary Cyanidin 3- O-?- d-Glucoside on Liver Ischemia–Reperfusion Injury in Rats

    Microsoft Academic Search

    Takanori Tsuda; Fumihiko Horio; Junzoh Kitoh; Toshihiko Osawa

    1999-01-01

    We recently reported that feeding cyanidin 3-O-?-d-glucoside (C3G), a typical anthocyanin pigment, lowered the serum thiobarbituric acid-reactive substance (TBARS) concentration and increased the oxidation resistance of the serum to lipid peroxidation in rats. These results suggest that C3G acts as a potent antioxidant in vivo when acute oxidative stress is encountered. In the present study, we evaluated whether feeding C3G

  19. Protective Effects of Amburoside A, a Phenol Glucoside from Amburana cearensis, against CCl4-lnduced Hepatotoxicity in Rats

    Microsoft Academic Search

    Francisco Noé Fonseca; Fábio Azevedo Pereira; Kirley M. Canut; Cícero F. B. Felipe; Márcia V. Pitombelra; Glauce S. B. Viana; Brasil Fortaleza

    The aim of this study was to investigate the pos- sible beneficial effects of amburoside A.AMB(4- (O-\\/3-D-glycopyranosyl )benzyl protocatechoate J. against carbon tetrachloride (CCI4)toxicity in rats. AMBis a phenol glucoside from the Brazilian medicinal plant Amburana cearensis. popularly used for the treatment of respiratory tract affec- tions. Acute AMB(25 and 50 mg\\/kg. i.p. or p.o.) treatments of CCl4-intoxicated rats significantiy

  20. C-Aryl glucoside SGLT2 inhibitors containing a biphenyl motif as potential anti-diabetic agents.

    PubMed

    Ding, Yuyang; Mao, Liufeng; Xu, Dengfeng; Xie, Hui; Yang, Ling; Xu, Hongjiang; Geng, Wenjun; Gao, Yong; Xia, Chunguang; Zhang, Xiquan; Meng, Qingyi; Wu, Donghai; Zhao, Junling; Hu, Wenhui

    2015-07-15

    A series of highly active C-aryl glucoside SGLT2 inhibitors containing a biphenyl motif were designed and synthesized for biological evaluation. Among the compounds tested, compound 16l demonstrated high inhibitory activity against SGLT2 (IC50=1.9nM) with an excellent pharmacokinetic profile. Further study indicated that the in vivo efficacy of compound 16l was comparable to that of dapagliflozin, suggesting that further development would be worthwhile. PMID:26026363

  1. Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies1-3

    Microsoft Academic Search

    Kelly R Walsh; Sara J Haak; Torsten Bohn; Qingguo Tian; Steven J Schwartz; Mark L Failla

    Background:Althoughsoyisoflavonoidshaveanumberofhealth- promotingbenefits,informationconcerningthesitesoftheirabsorp- tion and metabolism in humans remains limited. Isoflavonoid ab- sorption from the gut requires deconjugation of glucosides to aglycones. Objective: The objective was to investigate the role of the small intestine in isoflavonoid absorption and metabolism in humans. Design:Humansubjectswithfullyfunctionalgastrointestinaltracts (n 6) and ileostomy subjects (n 6) were fed a single soy meal containing 64.8 mg isoflavonoid aglycone equivalents

  2. LC determination and pharmacokinetic study of vitexin-4?-O-glucoside in rat plasma after oral administration

    Microsoft Academic Search

    Xun Liu; Dong Wang; Wenjie Zhang; Nan Wang; Siyuan Wang; Haibo Li; Xixiang Ying; Tingguo Kang

    2011-01-01

    A simple and specific high-performance liquid chromatography (HPLC) method was developed for the pharmacokinetic study of vitexin-4?-O-glucoside (VOG) in rats after oral administration. The plasma samples were deproteinised with methanol after the addition of an internal standard, hesperidin. HPLC analysis was performed on a Diamonsil C18 analytical column, using methanol ?0.5% aqueous phosphoric acid (45:55, v\\/v) as the mobile phase

  3. HPLC determination of malondialdehyde in ECV304 cell culture medium for measuring the antioxidant effect of vitexin-4?- O -glucoside

    Microsoft Academic Search

    Xi-xiang Ying; Hai-bo Li; Zheng-yun Chu; Yan-jun Zhai; Ai-jing Leng; Xun Liu; Chun Xin; Wen-jie Zhang; Ting-guo Kang

    2008-01-01

    To investigate the antioxidant effect of vitexin-4?-O-glucoside, a flavone glycoside, isolated from the leaves of Crataegus pinnatifida Bge. var. major, we developed a simple and sensitive high-performance liquid chromatography (HPLC) method to determine levels of malondialdehyde\\u000a (MDA) in ECV304 cell culture medium after induction by tert-butyl-hydroperoxide (TBHP). The preparation of analyzed samples involved a one-step derivatization with thiobarbituric acid\\u000a (TBA).

  4. LC determination and pharmacokinetic study of vitexin-4?-O-glucoside in rat plasma after oral administration

    Microsoft Academic Search

    Xun Liu; Dong Wang; Wenjie Zhang; Nan Wang; Siyuan Wang; Haibo Li; Xixiang Ying; Tingguo Kang

    2012-01-01

    A simple and specific high-performance liquid chromatography (HPLC) method was developed for the pharmacokinetic study of vitexin-4?-O-glucoside (VOG) in rats after oral administration. The plasma samples were deproteinised with methanol after the addition of an internal standard, hesperidin. HPLC analysis was performed on a Diamonsil C18 analytical column, using methanol ?0.5% aqueous phosphoric acid (45:55, v\\/v) as the mobile phase

  5. The mechanism of vitexin-4?-O-glucoside protecting ECV-304 cells against tertbutyl hydroperoxide induced injury

    Microsoft Academic Search

    Hai-bo Li; Xi-xiang Ying; Jia Lu

    2010-01-01

    The aim of this article is to investigate the mechanism of vitexin-4?-O-glucoside (VOG) protecting ECV-304 cells against tertbutyl hydroperoxide (TBHP)-induced injury. ECV-304 cell viability was measured by MTT assay. Apoptosis was determined by terminal deoxynucleotidyl transferase-mediated dUTP nick end-labelling (TUNEL) assay. Cellular morphological changes were observed using phase contrast microscopy. The change of relative mitochondrial transmembrane potential in the ECV-304

  6. Study on optimal production of 3-ketovalidoxylamine A CN lyase and glucoside 3-dehydrogenase by a newly isolated Stenotrophomonas maltrophilia

    Microsoft Academic Search

    Jian-Fen Zhang; Yu-Guo Zheng; Yin-Chu Shen

    2009-01-01

    3-Ketovalidoxylamine A C-N lyase and glucoside 3-dehydrogenase (G3DH), two key enzymes for valienamine synthesis, are produced by Stenotrophomonas maltrophilia. The condition of producing 3- ketovalidoxylamine A C-N lyase and G3DH was optimized. Validamycin A was showed to be suitable carbon source for C-N lyase and G3DH synthesis. Maximum C-N lyase production was achieved by adding 100 ml culture medium into

  7. Purification and characterization of the glucoside 3-dehydrogenase produced by a newly isolated Stenotrophomonas maltrophilia CCTCC M 204024

    Microsoft Academic Search

    Jian-Fen Zhang; Yu-Guo Zheng; Ya-Ping Xue; Yin-Chu Shen

    2006-01-01

    A soluble glucoside 3-dehydrogenase (G3DH) from Stenotrophomonas maltrophilia CCTCC M 204024, recently isolated from wheat soil in our laboratory, was purified to 37.4-fold with a yield of 24.7% and was estimated by sodium dodecyl sulfate-polyacrylamide gel electrophoresis with a molecular mass of 66 kDa. 2,6-Dichlorophenolindophenol (DCPIP) and ferricyanide were able to act as artificial electron acceptors for the enzyme. The optimal

  8. Inhibiting effects of resveratrol and its glucoside piceid against Venturia inaequalis, the causal agent of apple scab.

    PubMed

    Schulze, Katja; Schreiber, Lukas; Szankowski, Iris

    2005-01-26

    Resveratrol is a phytoalexin produced in different unrelated plant species such as grapevine and peanut. The effect of resveratrol and its glucoside trans-resveratrol-3-O-beta-D-glycopyranosid (piceid) against Venturia inaequalis, the causal agent of apple scab, was evaluated using a newly established test based on enzymatically isolated cuticular membranes (CMs) from apple (Malus domestica Borkh.) leaves. The test substances resveratrol and piceid were either sorbed to CMs before inoculation with spores or were applied simultaneously with the Venturia inaequalis spores to the CMs, and their effect on germination, appressoria formation, and penetration was examined. Resveratrol had no influence on spore germination but a significant inhibiting effect on penetration when applied simultaneously as well as before. A percentage inhibition of 89.7 +/- 11.5 and 61.8 +/- 35.1 was observed for simultaneous and preapplication, respectively. The resveratrol glucoside piceid had a significant inhibitory effect on germination and completely inhibited penetration of the fungus at concentrations between 200 and 400 microg mL(-1) when applied simultaneously with the spores to the CMs. On piceid-enriched CM (preapplication), spores germinated but penetration was inhibited nearly completely (96.1 +/- 5.1%). Thus, in vitro experiments showed that resveratrol and its glucoside in fact could contribute to improving the pathogen resistance of apple leaves. PMID:15656672

  9. Iridoid and secoiridoid glycosides in a hybrid complex of bush honeysuckles (Lonicera spp., Caprifolicaceae): implications for evolutionary ecology and invasion biology.

    PubMed

    Whitehead, Susan R; Bowers, M Deane

    2013-02-01

    Interspecific hybridization among non-native plant species can generate genotypes that are more reproductively successful in the introduced habitat than either parent. One important mechanism that may serve as a stimulus for the evolution of invasiveness in hybrids is increased variation in secondary metabolite chemistry, but still very little is known about patterns of chemical trait introgression in plant hybrid zones. This study examined the occurrence of iridoid and secoiridoid glycosides (IGs), an important group of plant defense compounds, in three species of honeysuckle, Lonicera morrowii A. Gray, Lonicera tatarica L., and their hybrid Lonicera×bella Zabel. (Caprifoliaceae), all of which are considered invasive in various parts of North America. Hybrid genotypes had a diversity of IGs inherited from both parent species, as well as one component not detected in either parent. All three species were similar in that overall concentrations of IGs were significantly higher in fruits than in leaves, and several compounds that were major components of fruits were never found in leaves. However, specific patterns of quantitative distribution among leaves, unripe fruits, and ripe fruits differed among the three species, with a relatively higher allocation to fruits in the hybrid species than for either parent. These patterns likely have important consequences for plant interactions with antagonistic herbivores and pathogens as well as mutualistic seed dispersers, and thus the potential invasiveness of hybrid and parental species in their introduced range. Methods established here for quantitative analysis of IGs will allow for the exploration of many compelling research questions related to the evolutionary ecology and invasion biology of these and other related species in the genus Lonicera. PMID:23228598

  10. Production of the UVB-absorbing compound mycosporine-glutaminol-glucoside by Xanthophyllomyces dendrorhous (Phaffia rhodozyma).

    PubMed

    Libkind, Diego; Moline, Martín; van Broock, María

    2011-02-01

    The ability of the basidiomycetous yeast Xanthophyllomyces dendrorhous (Phaffia rhodozyma) to accumulate astaxanthin is responsible for the industrial use of this yeast as a microbial source of pigments for aquaculture. It is also hypothesized that astaxanthin accounts for its ability to thrive in highly oxidative and UV-exposed habitats. Here, we assessed the ability of this species to synthesize UV-absorbing compounds generally known as mycosporines, evaluated the effect of culture media in the production of these compounds and compared its UV growth resistance and tolerance with other yeasts. The 48 wild and collection strains screened were positive for mycosporines and a unique compound identified as mycosporine-glutaminol-glucoside (MGG) was detected. Thus, the ability of X. dendrorhous to produce MGG, as described here for the first time, is so far unique among the Cystofilobasidiales. The compound was synthesized constitutively, although growth under visible light and, to a greater extent, UVA radiation stimulated its production. Strains from UV-exposed habitats produced larger quantities and oligotrophic complex media seemed to favor MGG accumulation. UV tolerance and survival of X. dendrorhous was high and comparable to that of the polyextremophilic Rhodotorula mucilaginosa. The taxonomical and ecological implications of the production of MGG by X. dendrorhous are discussed. PMID:20955516

  11. Cyanidin-3-glucoside isolated from mulberry fruits protects pancreatic ?-cells against glucotoxicity-induced apoptosis.

    PubMed

    Lee, Jong Seok; Kim, Young Rae; Park, Jun Myoung; Kim, Young Eon; Baek, Nam In; Hong, Eock Kee

    2015-04-01

    The present study investigated the cytoprotective effects of cyanidin?3?glucoside (C3G), isolated from mulberry fruits, on the glucotoxicity?induced apoptosis of pancreatic ??cells to evaluate the antidiabetic effects of this compound. MIN6N pancreatic ??cells were used to investigate the cytoprotective effects of C3G. In addition, the effects of C3G on the glucotoxicity?induced apoptosis of pancreatic ??cells was evaluated using MTT assay, immunofluorescent staining, flow cytometric and western blot analyses. The pancreatic ??cells cultured under high glucose conditions exhibited distinct apoptotic features. C3G decreased the generation of intracellular reactive oxygen species, DNA fragmentation and the rate of apoptosis. C3G also prevented pancreatic ??cell apoptosis induced by high glucose conditions by interfering with the intrinsic apoptotic pathways. In addition, C3G treatment resulted in increased insulin secretion compared with treatment with high glucose only. In conclusion, the results of the present study suggested that C3G obtained from mulberry fruits may be a potential phytotherapeutic agent for the prevention of diabetes. PMID:25501967

  12. Effect of heat/pressure on cyanidin-3-glucoside ethanol model solutions

    NASA Astrophysics Data System (ADS)

    Corrales, M.; Lindauer, R.; Butz, P.; Tauscher, B.

    2008-07-01

    The stability of cyanidin-3-glucoside (Cy3gl) in 50% ethanol model solutions under heat/pressure treatments was investigated. Cy3gl was rapidly degraded when solutions were subjected to a heat/pressure treatment. The higher the pressure and the temperature used, the higher the degradation. Moreover, the degradation was increased according to increasing holding times. Parallel to the degradation of Cy3gl several hydrolytic products were formed and identified by LC-DAD/ESI-MS. The degradation of Cy3gl was well fitted to a first order reaction (R=0.99). This study pointed out the rate of susceptibility of Cy3gl in model solutions to degrade when exposed to a heat/pressure treatment and the trigger effect of high hydrostatic pressure to hydrolyse Cy3gl. By contrast, the degradation of anthocyanins in a food matrix (red grape extract solutions) was negligible after a heat/pressure process at 600MPa, 70°C during 1h (P >0.05).

  13. Proteomic analysis for anti-atherosclerotic effect of tetrahydroxystilbene glucoside in rats.

    PubMed

    Yao, Wenjuan; Fan, Wenjun; Huang, Chao; Zhong, Hui; Chen, Xiangfan; Zhang, Wei

    2013-03-01

    2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG) extracted from Polygonum multiflorum (a traditional Chinese medicinal herb) has been proved to exhibit significant anti-atherosclerotic activity. In this study, we firstly used proteomic analyses to investigate the molecular events occurring in the atherosclerotic rats after TSG treatment. Aortic samples were collected from the atherosclerotic rat group and the TSG-treated group, and its proteome was analyzed by two-dimensional gel electrophoresis (2-DE). Proteins showing significant changes in expression were identified and analyzed by matrix-assisted desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS). As a result, 21 protein spots were found with significant differential expression after the treatment with TSG. A total of 18 spots were identified by database searching, and 17 spots matched with known proteins. Among these proteins (11 proteins up-regulated and six proteins down-regulated), five proteins were mainly involved in inflammation, cholesterol transport, cell apoptosis and adhesion. TSG treatment enhanced the expression of HSP 70, lipocortin 1 and Apo A-I, and inhibited the expression of calreticulin, vimentin. Furthermore, we randomly selected four proteins and confirmed the results of proteomic analysis by RT-PCR and western blotting. In conclusion, TSG treatment suppresses atherosclerosis by altering the expression of different proteins. Calreticulin, vimentin, HSP 70, lipocortin 1, and Apo A-I, are key proteins that may be novel molecular targets responsible for atherogenesis suppression induced by TSG treatment. PMID:23206751

  14. Souring and breakdown of cyanogenic glucosides during the processing of cassava into akyeke.

    PubMed

    Obilie, Eric Mantey; Tano-Debrah, Kwaku; Amoa-Awua, Wisdom Kofi

    2004-05-15

    The population and composition of the lactic acid bacteria microbiota as well as the content of cyanogenic glucosides occurring at various stages of fermentation and subsequent processing of cassava roots into akyeke, a steamed sour cassava meal, were investigated. The number of lactic acid bacteria and percentage titratable acidity increased during 5 days of fermentation, but decreases were observed in the subsequent operations of 'washing' the dough with water followed by partial drying and steaming. In field and laboratory samples, Lactobacillus plantarum accounted for 59.3% and 52.3%, Lactobacillus brevis 23.3% and 22.8% and Leuconostoc mesenteroides subsp. cremoris 14.5% and 15.8%, respectively, of all lactic acid bacteria isolated at various stages of fermentation and processing. A reduction of about 98% occurred in the total cyanogens (CN) content of cassava roots during processing, from 69.3 to 1.4 and 110.3 to 2.8 mg CN equivalent/kg dry weight for laboratory and field samples of akyeke, respectively. PMID:15135588

  15. Structural characterization of inclusion complexes between cyanidin-3-O-glucoside and ?-cyclodextrin.

    PubMed

    Fernandes, Ana; Ivanova, Galya; Brás, Natércia F; Mateus, Nuno; Ramos, Maria J; Rangel, Maria; de Freitas, Victor

    2014-02-15

    Inclusion complex formation between the multiple equilibrium forms of cyanidin-3-O-glucoside (cy3glc) and ?-cyclodextrin (?-CD) was investigated using a combined approach of NMR spectroscopy and Molecular Dynamics simulation. Diffusion ordered NMR spectroscopy (DOSY) and study of nuclear Overhauser effects (NOE) were used to determine the selective intermolecular interactions and structure of these complexes in aqueous solution. The observed chemical shift displacements of resonance signals of protons from the interior of ?-CD cavity and protons belonging to the hemiketal (B) and cis-chalcone forms (Cc), the diffusion measurements using DOSY and the NOE studies have anticipated the formation of an inclusion complex between these two forms and ?-CD. The analysis of the NMR spectral data has shown no evidence of internal interaction between ?-CD and the flavylium cation (AH(+)) or trans-chalcone (Ct) forms of cy3glc. The hemiketal formed a 1:1 inclusion complex with ?-cyclodextrin in which the pyranic C ring is deeply included inside the ?-CD cavity while B ring lies on the plane of the wider rim of ?-CD. The structure of the complexes was also clarified through a theoretical approach by Molecular Dynamics simulation. PMID:24507282

  16. A Natural Flavonoid Glucoside, Icariin, Regulates Th17 and Alleviates Rheumatoid Arthritis in a Murine Model

    PubMed Central

    Chi, Liqun; Gao, Wenyuan; Shu, Xiangrong; Lu, Xin

    2014-01-01

    Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease that causes deformity of the joints and physical disability. Icariin, a natural flavonoid glucoside isolated from plants in the Epimedium family, has been proven to have various pharmacological activities. A recent study showed that icariin suppressed cartilage and bone degradation in mice of collagen-induced arthritis. However, the mechanism needs to be further investigated. In our current study, we found that icariin reduced the arthritis score and the incidence of arthritis compared with that in mice treated with water. Icariin inhibits the expression of various osteoclastogenic markers, such as ?3 integrin, cathepsin K, and MMP9 in vitro. Icariin treatment in mice with CIA also resulted in less number of Th17 cells and decreased ratio of CD4+IL-17+ cells. The alleviated arthritis score and incidence of arthritis and reduced serum levels of IgG2a induced by icariin were abolished with additional IL-17 administration. Furthermore, icariin inhibited STAT3 activation in T cells and STAT3 inhibitor resulted in decreased IL-17 production and alleviated RA. In conclusion, icariin decreases Th17 cells and suppresses the production of IL-17, which contributes to the alleviated rheumatoid arthritis, through the inhibition of STAT3 activation. PMID:25374443

  17. A natural flavonoid glucoside, icariin, regulates Th17 and alleviates rheumatoid arthritis in a murine model.

    PubMed

    Chi, Liqun; Gao, Wenyuan; Shu, Xiangrong; Lu, Xin

    2014-01-01

    Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease that causes deformity of the joints and physical disability. Icariin, a natural flavonoid glucoside isolated from plants in the Epimedium family, has been proven to have various pharmacological activities. A recent study showed that icariin suppressed cartilage and bone degradation in mice of collagen-induced arthritis. However, the mechanism needs to be further investigated. In our current study, we found that icariin reduced the arthritis score and the incidence of arthritis compared with that in mice treated with water. Icariin inhibits the expression of various osteoclastogenic markers, such as ?3 integrin, cathepsin K, and MMP9 in vitro. Icariin treatment in mice with CIA also resulted in less number of Th17 cells and decreased ratio of CD4(+)IL-17(+) cells. The alleviated arthritis score and incidence of arthritis and reduced serum levels of IgG2a induced by icariin were abolished with additional IL-17 administration. Furthermore, icariin inhibited STAT3 activation in T cells and STAT3 inhibitor resulted in decreased IL-17 production and alleviated RA. In conclusion, icariin decreases Th17 cells and suppresses the production of IL-17, which contributes to the alleviated rheumatoid arthritis, through the inhibition of STAT3 activation. PMID:25374443

  18. Cancer chemopreventive potential of luteolin-7-O-glucoside isolated from Ophiorrhiza mungos Linn.

    PubMed

    Baskar, Arul Albert; Ignacimuthu, Savarimuthu; Michael, Gabriel Paulraj; Al Numair, Khalid S

    2011-01-01

    The anticarcinogenic potential of the phytocompound Luteolin-7-O-Glucoside (LUT7G), isolated from the leaves of Ophiorrhiza mungos Linn, was studied against 4 different cancer cell lines (COLO 320 DM, AGS, MCF-7, and A549) and normal VERO cell line. The ability of LUT7G to induce apoptosis was determined by its antiradical activity, DNA fragmentation, expression of ?-catenin, and chemopreventive efficacy in vivo by administering rats with DMH (20 mg/kg b.w., s.c.) for 4 consecutive wk and supplementing with 3 different doses throughout the experimental period of 16 wk. LUT7G scavenged 80% of DPPH radicals generated in vitro at 1000 ?M and suppressed the expression of ?-catenin to 40% at 120 ?M concentrations. LUT7G induced apoptosis by scavenging ROS and suppressing the expression of ?-catenin in COLO 320 DM cells and effectively inhibited ACF development in DMH-induced experimental carcinogenesis. Hence LUT7G can be a potent anticancer drug for colon carcinogenesis. PMID:21161823

  19. Analysis of Deoxynivalenol and Deoxynivalenol-3-glucoside in Hard Red Spring Wheat Inoculated with Fusarium Graminearum

    PubMed Central

    Ovando-Martínez, Maribel; Ozsisli, Bahri; Anderson, James; Whitney, Kristin; Ohm, Jae-Bom; Simsek, Senay

    2013-01-01

    Deoxynivalenol (DON) is a mycotoxin affecting wheat quality. The formation of the “masked” mycotoxin deoxinyvalenol-3-glucoside (D3G) results from a defense mechanism the plant uses for detoxification. Both mycotoxins are important from a food safety point of view. The aim of this work was to analyze DON and D3G content in inoculated near-isogenic wheat lines grown at two locations in Minnesota, USA during three different years. Regression analysis showed positive correlation between DON content measured with LC and GC among wheat lines, locality and year. The relationship between DON and D3G showed a linear increase until a certain point, after which the DON content and the D3G increased. Wheat lines having higher susceptibility to Fusarium showed the opposite trend. ANOVA demonstrated that the line and location have a greater effect on variation of DON and D3G than do their interaction among years. The most important factor affecting DON and D3G was the growing location. In conclusion, the year, environmental conditions and location have an effect on the D3G/DON ratio in response to Fusarium infection. PMID:24351715

  20. Effects of iriflophenone 3-C-?-glucoside on fasting blood glucose level and glucose uptake

    PubMed Central

    Pranakhon, Ratree; Aromdee, Chantana; Pannangpetch, Patchareewan

    2015-01-01

    Background: One of the biological activities of agar wood (Aquilaria sinensis Lour., Thymelaeaceae), is anti-hyperglycemic activity. The methanolic extract (ME) was proven to possess the fasting blood glucose activity in rat and glucose uptake transportation by rat adipocytes. Objective: To determine the decreasing fasting blood glucose level of constituents affordable for in vivo test. If the test was positive, the mechanism which is positive to the ME, glucose transportation, will be performed. Materials and Methods: The ME was separated by column chromatography and identified by spectroscopic methods. Mice was used as an animal model (in vivo), and rat adipocytes were used for the glucose transportation activity (in vitro). Result: Iriflophenone 3-C-?-glucoside (IPG) was the main constituent, 3.17%, and tested for the activities. Insulin and the ME were used as positive controls. The ME, IPG and insulin lowered blood glucose levels by 40.3, 46.4 and 41.5%, respectively, and enhanced glucose uptake by 152, 153, and 183%, respectively. Conclusion: These findings suggest that IPG is active in lowering fasting blood glucose with potency comparable to that of insulin. PMID:25709215

  1. Expression of a zeatin-O-glucoside-degrading beta-glucosidase in Brassica napus.

    PubMed Central

    Falk, A; Rask, L

    1995-01-01

    A beta-glucosidase was purified from seeds of Brassica napus L. (oilseed rape). The 130-kD native enzyme consisted of a disulfide-linked dimer of 64-kD monomers. Internal amino acid sequences were used to construct degenerate primers for polymerase chain reaction-mediated cloning of cDNA for the enzyme. One nearly full-length and one partial beta-glucosidase-encoding cDNA clone were isolated and sequenced. Southern hybridization showed that beta-glucosidase is encoded by a small gene family in B. napus. Northern hybridization showed that the genes are expressed in the seed, with a low degree of expression in other tissues. In the seed, the expression started at 30 days after pollination (DAP), with the highest expression at 40 DAP. The size of the transcript was approximately 1900 nucleotides. In situ hybridization to developing seeds of B. napus showed that the beta-glucosidase expression started at 30 DAP around the provascular tissue in the embryo axis. In the cotyledons, mRNA initially accumulated around the provascular tissues but was detected first at 35 DAP. At 40 DAP, expression occurred in most parts of the seed. In situ hybridization also detected beta-glucosidase mRNA in shoots, young roots, and the basal part of the hypocotyls. Zeatin-O-glucoside was identified as a natural substrate for B. napus beta-glucosidase. PMID:7659745

  2. PLS-Prediction and Confirmation of Hydrojuglone Glucoside as the Antitrypanosomal Constituent of Juglans Spp.

    PubMed

    Ellendorff, Therese; Brun, Reto; Kaiser, Marcel; Sendker, Jandirk; Schmidt, Thomas J

    2015-01-01

    Naphthoquinones (NQs) occur naturally in a large variety of plants. Several NQs are highly active against protozoans, amongst them the causative pathogens of neglected tropical diseases such as human African trypanosomiasis (sleeping sickness), Chagas disease and leishmaniasis. Prominent NQ-producing plants can be found among Juglans spp. (Juglandaceae) with juglone derivatives as known constituents. In this study, 36 highly variable extracts were prepared from different plant parts of J. regia, J. cinerea and J. nigra. For all extracts, antiprotozoal activity was determined against the protozoans Trypanosoma cruzi, T. brucei rhodesiense and Leishmania donovani. In addition, an LC-MS fingerprint was recorded for each extract. With each extract's fingerprint and the data on in vitro growth inhibitory activity against T. brucei rhodesiense a Partial Least Squares (PLS) regression model was calculated in order to obtain an indication of compounds responsible for the differences in bioactivity between the 36 extracts. By means of PLS, hydrojuglone glucoside was predicted as an active compound against T. brucei and consequently isolated and tested in vitro. In fact, the pure compound showed activity against T. brucei at a significantly lower cytotoxicity towards mammalian cells than established antiprotozoal NQs such as lapachol. PMID:26035104

  3. Enzymatic synthesis of piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii DSM 6725.

    PubMed

    Park, Hyunsu; Kim, Jieun; Choi, Kyoung-Hwa; Hwang, Sungmin; Yang, Sung-Jae; Baek, Nam-In; Cha, Jaeho

    2012-08-22

    Piceid is widely used in food, cosmetics, and pharmaceuticals because of its therapeutic benefits. However, the use of piceid as a drug is limited because of its low solubility. To increase solubility, we synthesized piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii. The MTase gene was cloned and expressed in Escherichia coli. The enzyme had a unique transfer specificity to the transfer of maltosyl units. Four piceid transglycosylation products were present and identified by thin-layer chromatography and recycling preparative high-performance liquid chromatography. The major product was purified by C(18) and gel filtration chromatography, and its molecular structure was determined using nuclear magnetic resonance spectroscopy to be ?-D-maltosyl-(1?4)-piceid. The solubility of maltosyl piceid was 8.54 × 10(3) and 1.86 × 10(3) times those of natural resveratrol and piceid, respectively, suggesting that the transglycosylation greatly increased the water solubility. This suggests that dietary intake of this compound can enhance the bioavailability of resveratrol in the human body. PMID:22823185

  4. Enzymatic hydrolysis of steryl glucosides, major contaminants of vegetable oil-derived biodiesel.

    PubMed

    Aguirre, Andres; Peiru, Salvador; Eberhardt, Florencia; Vetcher, Leandro; Cabrera, Rodolfo; Menzella, Hugo G

    2014-05-01

    Biodiesels are mostly produced from lipid transesterification of vegetable oils, including those from soybean, jatropha, palm, rapeseed, sunflower, and others. Unfortunately, transesterification of oil produces various unwanted side products, including steryl glucosides (SG), which precipitate and need to be removed to avoid clogging of filters and engine failures. So far, efficient and cost-effective methods to remove SGs from biodiesel are not available. Here we describe for the first time the identification, characterization and heterologous production of an enzyme capable of hydrolyzing SGs. A synthetic codon-optimized version of the lacS gene from Sulfolobus solfataricus was efficiently expressed and purified from Escherichia coli, and used to treat soybean derived biodiesel containing 100 ppm of SGs. After optimizing different variables, we found that at pH 5.5 and 87 °C, and in the presence of 0.9 % of the emulsifier polyglycerol polyricinoleate, 81 % of the total amount of SGs present in biodiesel were hydrolyzed by the enzyme. This remarkable reduction in SGs suggests a path for the removal of these contaminants from biodiesel on industrial scale using an environmentally friendly enzymatic process. PMID:24265025

  5. Cyanidin-3-glucoside isolated from mulberry fruit protects pancreatic ?-cells against oxidative stress-induced apoptosis.

    PubMed

    Lee, Jong Seok; Kim, Young Rae; Song, In Gyu; Ha, Suk-Jin; Kim, Young Eon; Baek, Nam-In; Hong, Eock Kee

    2015-02-01

    The extract obtained from berries contains high amounts of anthocyanins, and this extract is used as a phytotherapeutic agent for different types of diseases. In this study, we examined the cytoprotective effects of cyanidin-3-glucoside (C3G) isolated from mulberry fruit against pancreatic ?-cell apoptosis caused by hydrogen peroxide (H2O2)-induced oxidative stress. The MIN6 pancreatic ?-cells were used to investigate the cytoprotective effects of C3G on the oxidative stress-induced apoptosis of cells. Cell viability was examined by MTT assay and lipid peroxidation was assayed by thiobarbituric acid (TBA) reaction. Immunofluorescence staining, flow cytometry and western blot analysis were also used to determine apoptosis and the expression of proteins associated with apoptosis. Our results revealed that H2O2 increased the rate of apoptosis by stimulating various pro-apoptotic processes, such as the generation of intracellular reactive oxygen species (ROS), lipid peroxidation, DNA fragmentation and caspase-3 activation. However, C3G reduced the H2O2-induced cell death in the MIN6N pancreatic ?-cells. In addition, we confirmed that H2O2 activated mitogen-activated protein kinases (MAPKs), such as extracellular signal-regulated kinase (ERK), c-Jun NH2-terminal kinase (JNK) and p38 MAPK. C3G inhibited the phosphorylation of ERK and p38 without inducing the phosphorylation of JNK. Furthermore, C3G regulated the intrinsic apoptotic pathway-associated proteins, such as proteins belonging to the Bcl-2 family, cytochrome c and caspase-3. Taken together, our results suggest that C3G isolated from mulberry fruit has potential for use as a phytotherapeutic agent for the prevention of diabetes by preventing oxidative stress-induced ?-cell apoptosis. PMID:25435295

  6. Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts.

    PubMed

    Funari, Cristiano Soleo; Passalacqua, Thais Gaban; Rinaldo, Daniel; Napolitano, Assunta; Festa, Michela; Capasso, Anna; Piacente, Sonia; Pizza, Cosimo; Young, Maria Claudia Marx; Durigan, Giselda; Silva, Dulce Helena Siqueira

    2011-11-01

    Four interconverting flavanone glycosides [(2R)- and (2S)-3',4',5,6-tetrahydroxyflavanone 7-O-?-D-glucopyranoside, and (2R)- and (2S)-3',4',5,8-tetrahydroxyflavanone 7-O-?-D-glucopyranoside], in addition to eight known flavonoids [naringenin, asebogenin, sakuranetin, 6-hydroxyluteolin 7-O-?-D-glucoside, (2R)- and (2S)-eriodictyol 7-O-?-D-glucopyranoside, aromadendrin and phloretin], three phenylpropanoid glycosides [forsythoside B, alyssonoside and verbascoside] and the epoxylignan lariciresinol 4'-O-?-D-glucopyranoside were isolated and identified in the EtOH extract of the aerial parts of Lippia salviaefolia Cham. The phytochemical study herein was guided by preliminary antioxidant tests, namely, ?-carotene protection and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity. The crude extracts, their active fractions and the isolated compounds were assayed against intracellular reactive oxygen species (ROS) and human embryonic kidney HEK-293 and human melanoma M14 cancer cell growth. Aromadendrin and phloretin were able to counteract elevation of ROS induced by the oxidant t-butylhydroperoxide (t-BOOH) in HEK-293 cells, whereas phloretin strongly protected HEK-293 cells from ROS damage at 1 ?M. Additionally, phloretin exhibited a significant growth inhibitory effect at 20-40 ?M in both HEK-293 and M14 cells and induced a concentration dependent apoptosis at 20 ?M in M14 cells, suggesting a selective action towards malignant cells. Due to their equilibria, the four interconverting flavanone glycosides were studied using 1D and 2D NMR, HPLC-CD-PDA and HRMS analyses. PMID:21871644

  7. Identification and characterization of a new beta-glucoside utilization system in Bacillus subtilis.

    PubMed Central

    Tobisch, S; Glaser, P; Krüger, S; Hecker, M

    1997-01-01

    A new catabolic system in Bacillus subtilis involved in utilization of beta-glucosidic compounds has been investigated. It consists of five genes encoding phosphotransferase system (PTS) enzyme II (licB and licC) and enzyme IIA (licA), a presumed 6-phospho-beta-glucosidase (licH), as well as a putative regulator protein (licR). The genes map around 334 degrees of the B. subtilis chromosome, and their products are involved in the uptake and utilization of lichenan degradation products. These five genes are organized in two transcriptional units. A weak promoter precedes gene licR, and transcription is obviously terminated at a secondary structure immediately downstream of the reading frame, as shown by Northern RNA blot analysis. Genes licB, licC, licA, and licH constitute an operon. Initiation of transcription at the promoter in front of this operon presumably requires activation by the gene product of licR. The LicR protein shows an unusual domain structure, i.e., similarities to (i) the conserved transcriptional antiterminator BgIG family signature and (ii) PTS enzyme II. Using RNA techniques and transcriptional lacZ fusions, we have shown that the expression of the licBCAH operon is inducible by products of lichenan hydrolysis, lichenan and cellobiose. The presence of excess glucose prevents the induction of this operon, indicating the control by carbon catabolite repression. Moreover, the expression of the operon requires the general PTS components and seems to be negatively controlled by the specific lic PTS enzymes. PMID:8990303

  8. Total glucosides of paeony prevents juxta-articular bone loss in experimental arthritis

    PubMed Central

    2013-01-01

    Background Total glucosides of paeony (TGP) is a biologically active compound extracted from Paeony root. TGP has been used in rheumatoid arthritis therapy for many years. However, the mechanism by which TGP prevents bone loss has been less explored. Methods TGP was orally administered for 3 months to New Zealand rabbits with antigen-induced arthritis (AIA). Digital x-ray knee images and bone mineral density (BMD) measurements of the subchondral knee bone were performed before sacrifice. Chondrocytes were observed using transmission electron microscopy (TEM). Histological analysis and mRNA expression of receptor activator of nuclear factor-B ligand (RANKL) and osteoprotegerin (OPG) were evaluated in joint tissues. Results The BMD value in TGP rabbits was significantly higher compared with that seen in the AIA model rabbits. In addition, the subchondral bone plate was almost completely preserved by TGP treatment, while there was a decrease in bone plate integrity in AIA rabbits. There was less damage to the chondrocytes of the TGP treated group. Immunohistochemical examination of the TGP group showed that a higher percentage of TGP treated chondrocytes expressed OPG as compared to the chondrocytes isolated from AIA treated animals. In contrast, RANKL expression was significantly decreased in the TGP treated group compared to the AIA group. In support of the immunohistochemistry data, the expression of RANKL mRNA was decreased and OPG mRNA expression was enhanced in the TGP group when compared to that of the AIA model group. Conclusion These results reveal that TGP suppresses juxta-articular osteoporosis and prevents subchondral bone loss. The decreased RANKL and increased OPG expression seen in TGP treated animals could explain how administration of TGP maintains higher BMD. PMID:23870279

  9. The Flavonoid Luteolin, but Not Luteolin-7-O-Glucoside, Prevents a Transthyretin Mediated Toxic Response

    PubMed Central

    Pokrzywa, Malgorzata; Walfridsson, Malin; Sauer-Eriksson, A. Elisabeth; Olofsson, Anders

    2015-01-01

    Transthyretin (TTR) is a homotetrameric plasma protein with amyloidogenic properties that has been linked to the development of familial amyloidotic polyneuropathy (FAP), familial amyloidotic cardiomyopathy, and senile systemic amyloidosis. The in vivo role of TTR is associated with transport of thyroxine hormone T4 and retinol-binding protein. Loss of the tetrameric integrity of TTR is a rate-limiting step in the process of TTR amyloid formation, and ligands with the ability to bind within the thyroxin binding site (TBS) can stabilize the tetramer, a feature that is currently used as a therapeutic approach for FAP. Several different flavonoids have recently been identified that impair amyloid formation. The flavonoid luteolin shows therapeutic potential with low incidence of unwanted side effects. In this work, we show that luteolin effectively attenuates the cytotoxic response to TTR in cultured neuronal cells and rescues the phenotype of a Drosophila melanogaster model of FAP. The plant-derived luteolin analogue cynaroside has a glucoside group in position 7 of the flavone A-ring and as opposed to luteolin is unable to stabilize TTR tetramers and thus prevents a cytotoxic effect. We generated high-resolution crystal-structures of both TTR wild type and the amyloidogenic mutant V30M in complex with luteolin. The results show that the A-ring of luteolin, in contrast to what was previously suggested, is buried within the TBS, consequently explaining the lack of activity from cynaroside. The flavonoids represent an interesting group of drug candidates for TTR amyloidosis. The present investigation shows the potential of luteolin as a stabilizer of TTR in vivo. We also show an alternative orientation of luteolin within the TBS which could represent a general mode of binding of flavonoids to TTR and is of importance concerning the future design of tetramer stabilizing drugs. PMID:26020516

  10. Eriodictyol-7-O-glucoside activates Nrf2 and protects against cerebral ischemic injury

    SciTech Connect

    Jing, Xu [Department of Pharmacology, School of Medicine, Shandong University, Jinan 250012 (China); Ren, Dongmei [Department of Natural Product Chemistry, Key Lab of Chemical Biology of Ministry of Education, Shandong University, Jinan 250012 (China); Wei, Xinbing; Shi, Huanying; Zhang, Xiumei [Department of Pharmacology, School of Medicine, Shandong University, Jinan 250012 (China); Perez, Ruth G. [Health Science Center, Paul L. Foster School of Medicine, Texas Tech University, El Paso, TX, 79905 (United States); Lou, Haiyan, E-mail: louhaiyan@sdu.edu.cn [Department of Pharmacology, School of Medicine, Shandong University, Jinan 250012 (China); Lou, Hongxiang [Department of Natural Product Chemistry, Key Lab of Chemical Biology of Ministry of Education, Shandong University, Jinan 250012 (China)

    2013-12-15

    Stroke is a complex disease that may involve oxidative stress-related pathways in its pathogenesis. The nuclear factor erythroid-2-related factor 2/antioxidant response element (Nrf2/ARE) pathway plays an important role in inducing phase II detoxifying enzymes and antioxidant proteins and thus has been considered a potential target for neuroprotection in stroke. The aim of the present study was to determine whether eriodictyol-7-O-glucoside (E7G), a novel Nrf2 activator, can protect against cerebral ischemic injury and to understand the role of the Nrf2/ARE pathway in neuroprotection. In primary cultured astrocytes, E7G increased the nuclear localization of Nrf2 and induced the expression of the Nrf2/ARE-dependent genes. Exposure of astrocytes to E7G provided protection against oxygen and glucose deprivation (OGD)-induced oxidative insult. The protective effect of E7G was abolished by RNA interference-mediated knockdown of Nrf2 expression. In vivo administration of E7G in a rat model of focal cerebral ischemia significantly reduced the amount of brain damage and ameliorated neurological deficits. These data demonstrate that activation of Nrf2/ARE signaling by E7G is directly associated with its neuroprotection against oxidative stress-induced ischemic injury and suggest that targeting the Nrf2/ARE pathway may be a promising approach for therapeutic intervention in stroke. - Highlights: • E7G activates Nrf2 in astrocytes. • E7G stimulates expression of Nrf2-mediated cytoprotective proteins in astrocytes. • E7G protects astrocytes against OGD-induced cell death and apoptosis. • The neuroprotective effect of E7G involves the Nrf2/ARE pathway. • E7G protects rats against cerebral ischemic injury.

  11. Kinetic analysis of the degradation and its color change of cyanidin-3-glucoside exposed to pulsed electric field

    Microsoft Academic Search

    Yan Zhang; Xiaojun Liao; Yuanying Ni; Jihong Wu; Xiaosong Hu; Zhengfu Wang; Fang Chen

    2007-01-01

    The degradation and its corresponding color change of cyaniding-3-glucoside (Cy-3-glu) exposed to pulsed electric field (PEF)\\u000a was investigated in the study. In an aqueous-methanol solution of H2O (0.5% TFA) and methanol (MeOH) (7:3, v\\/v), the degradation of Cy-3-glu, which was exposed to PEF at 1.2, 2.2 and 3.3 kV\\/cm,\\u000a was increased as the electric field intensity and the treatment time increased

  12. Hypolipidemic and antioxidant effects of hydroxycinnamic acids, quercetin, and cyanidin 3-glucoside in hypercholesterolemic erythrocytes (in vitro study)

    Microsoft Academic Search

    Piotr Duchnowicz; Marlena Broncel; Anna Pods?dek; Maria Koter-Michalak

    Objective  Four polyphenols: ferulic acid and p-coumaric acid (hydroxycinnamic acids), quercetin (flavonol) and cyanidin 3-glucoside (anthocyanin) were selected, and their\\u000a antioxidant properties and their influence on cholesterol concentration in hypercholesterolemic and normal erythrocytes were\\u000a investigated.\\u000a \\u000a \\u000a \\u000a \\u000a Methods  To determine the effect of phenolic compounds, we prospectively studied cholesterol concentration, lipid peroxidation and\\u000a membranes fluidity. Whole-blood and isolated erythrocytes (2% hematocrit) were incubated for

  13. Absorption and metabolism of anthocyanincyanidin-3-glucoside in the isolated ratsmall intestine is not influenced by ethanol

    Microsoft Academic Search

    Wilfried Andlauer; Claudia Stumpf; Konstanze Frank; Peter Fürst

    2003-01-01

    Summary.  \\u000a\\u000a Anthocyanins are receiving\\u000arenewed attention for their\\u000apositive health attributes. High intakes\\u000aand an adequate absorption\\u000arate of anthocyanins are necessary\\u000afor efficient protection, though\\u000aother dietary agents might influence\\u000aabsorption efficacy. The aim\\u000aof this study was to investigate intestinal\\u000ahandling of luminally administered\\u000acyanidin-3-glucoside in\\u000athe absence and presence of\\u000aethanol in an isolated preparation\\u000aof luminally

  14. Synthesis of zearalenone-16-?,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

    PubMed Central

    Weber, Julia; Svatunek, Dennis; Skrinjar, Philipp; Adam, Gerhard; Krska, Rudolf; Hametner, Christian; Fröhlich, Johannes

    2014-01-01

    Summary The development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are difficult to access up to now. Acetyl and p-methoxybenzyl protection led to undesired results and were shown to be inappropriate. Finally, triisopropylsilyl-protected zearalenone was successfully used as intermediate for the first synthesis of the corresponding mycotoxin glucoside and sulfate that are highly valuable as reference materials for further studies in the emerging field of masked mycotoxins. Furthermore, high stability was observed for aryl sulfates prepared as tetrabutylammonium salts. Overall, these findings should be applicable for the synthesis of similar RAL type and natural product conjugates. PMID:24991263

  15. cDNA Cloning, Heterologous Expressions, and Functional Characterization of Malonyl-Coenzyme A:Anthocyanidin 3-O-Glucoside-6-O-Malonyltransferase from Dahlia Flowers1

    Microsoft Academic Search

    Hirokazu Suzuki; Toru Nakayama; Keiko Yonekura-Sakakibara; Yuko Fukui; Noriko Nakamura; Masa-atsu Yamaguchi; Yoshikazu Tanaka; Takaaki Kusumi; Tokuzo Nishino

    In the flowers of important ornamental Compositae plants, anthocyanins generally carry malonyl group(s) at their 3-glucosyl moiety. In this study, for the first time to our knowledge, we have identified a cDNA coding for this 3-glucoside-specific malonyltransferase for anthocyanins, i.e. malonyl-coenzyme A:anthocyanidin 3-O-glucoside-6-O-malonyltransferase, from dahlia (Dahlia variabilis) flowers. We isolated a full-length cDNA (Dv3MaT) on the basis of amino acid

  16. Occurrence and fate of the norsesquiterpene glucoside ptaquiloside (PTA) in soils

    NASA Astrophysics Data System (ADS)

    Zaccone, Claudio; Cavoski, Ivana; Costi, Roberta; Sarais, Giorgia; Caboni, Pierluigi; Miano, Teodoro M.; Lattanzio, Vincenzo

    2014-05-01

    The bracken fern Pteridium aquilinum (L.) Kuhn, one of the most common plant species on Earth, produces a wide range of secondary metabolites including the norsesquiterpene glucoside ptaquiloside (PTA). This bracken constituent causes acute poisoning, blindness and cancer in animals, and can be transferred to man when bracken is utilized as food. Also milk from cows eating bracken is thought to be the vector for the transfer of PTA to humans, as well as PTA-contaminated drinking waters. Although some studies on the effect of growth conditions and soil properties on the production and mobility of PTA have been carried out (mainly in the North of Europe), results are sometimes conflicting and further investigations are needed. The aim of the present work is to study the occurrence and the fate of PTA in soils showing different physico-chemical features, collected in different pedoclimatic areas (from the South of Italy), but having the extensive ("wild") livestock farming as common denominator. The PTA content was determined in both soil and fern samples by GC-MS; both the extraction protocol and recovery were previously tested through incubation studies. Soils samples were also characterizes from the physical and chemical point of view (pH, EC, texture, total carbonates, cation exchange capacity, organic C, total N, available nutrients and heavy metal concentration) in order to correlate the possible influence of soil parameters on PTA production, occurrence and mobility. PTA concentration in soil samples was always

  17. Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging.

    PubMed

    Dalisay, Doralyn S; Kim, Kye Won; Lee, Choonseok; Yang, Hong; Rübel, Oliver; Bowen, Benjamin P; Davin, Laurence B; Lewis, Norman G

    2015-06-26

    An integrated omics approach using genomics, transcriptomics, metabolomics (MALDI mass spectrometry imaging, MSI), and bioinformatics was employed to study spatiotemporal formation and deposition of health-protecting polymeric lignans and plant defense cyanogenic glucosides. Intact flax (Linum usitatissimum) capsules and seed tissues at different development stages were analyzed. Transcriptome analyses indicated distinct expression patterns of dirigent protein (DP) gene family members encoding (-)- and (+)-pinoresinol-forming DPs and their associated downstream metabolic processes, respectively, with the former expressed at early seed coat development stages. Genes encoding (+)-pinoresinol-forming DPs were, in contrast, expressed at later development stages. Recombinant DP expression and DP assays also unequivocally established their distinct stereoselective biochemical functions. Using MALDI MSI and ion mobility separation analyses, the pinoresinol downstream derivatives, secoisolariciresinol diglucoside (SDG) and SDG hydroxymethylglutaryl ester, were localized and detectable only in early seed coat development stages. SDG derivatives were then converted into higher molecular weight phenolics during seed coat maturation. By contrast, the plant defense cyanogenic glucosides, the monoglucosides linamarin/lotaustralin, were detected throughout the flax capsule, whereas diglucosides linustatin/neolinustatin only accumulated in endosperm and embryo tissues. A putative biosynthetic pathway to the cyanogens is proposed on the basis of transcriptome coexpression data. Localization of all metabolites was at ca. 20 ?m resolution, with the web based tool OpenMSI enabling not only resolution enhancement but also an interactive system for real-time searching for any ion in the tissue under analysis. PMID:25981198

  18. Biochemical Characterization of a Recombinant UDP-glucosyltransferase from Rice and Enzymatic Production of Deoxynivalenol-3-O-?-D-glucoside.

    PubMed

    Michlmayr, Herbert; Malachová, Alexandra; Varga, Elisabeth; Kleinová, Jana; Lemmens, Marc; Newmister, Sean; Rayment, Ivan; Berthiller, Franz; Adam, Gerhard

    2015-01-01

    Glycosylation is an important plant defense mechanism and conjugates of Fusarium mycotoxins often co-occur with their parent compounds in cereal-based food and feed. In case of deoxynivalenol (DON), deoxynivalenol-3-O-?-D-glucoside (D3G) is the most important masked mycotoxin. The toxicological significance of D3G is not yet fully understood so that it is crucial to obtain this compound in pure and sufficient quantities for toxicological risk assessment and for use as an analytical standard. The aim of this study was the biochemical characterization of a DON-inactivating UDP-glucosyltransferase from rice (OsUGT79) and to investigate its suitability for preparative D3G synthesis. Apparent Michaelis constants (Km) of recombinant OsUGT79 were 0.23 mM DON and 2.2 mM UDP-glucose. Substrate inhibition occurred at DON concentrations above 2 mM (Ki = 24 mM DON), and UDP strongly inhibited the enzyme. Cu2+ and Zn2+ (1 mM) inhibited the enzyme completely. Sucrose synthase AtSUS1 was employed to regenerate UDP-glucose during the glucosylation reaction. With this approach, optimal conversion rates can be obtained at limited concentrations of the costly co-factor UDP-glucose. D3G can now be synthesized in sufficient quantity and purity. Similar strategies may be of interest to produce ?-glucosides of other toxins. PMID:26197338

  19. Intestinal SGLT1-mediated absorption and metabolism of benzyl ?-glucoside contained in Prunus mume: carrier-mediated transport increases intestinal availability

    Microsoft Academic Search

    Takashi Mizuma; Maya Nakamura; Hiroji Ina; Toshio Miyazaki; Masahiro Hayashi

    2005-01-01

    The intestinal absorption of benzyl ?-glucoside (BNZ?glc) contained in the fruit of Prunus mume SIEB. et ZUCC. (Rosaceae), which is traditionally used as a medicinal food in Japan, was studied in rat intestines. BNZ?glc was absorbed from the mucosal to serosal sides. Its metabolite, benzyl alcohol (BAL), was also detected on both the mucosal and serosal sides. In the presence

  20. A Versatile Family 3 Glycoside Hydrolase from Bifidobacterium adolescentis Hydrolyzes ?-Glucosides of the Fusarium Mycotoxins Deoxynivalenol, Nivalenol, and HT-2 Toxin in Cereal Matrices.

    PubMed

    Michlmayr, Herbert; Varga, Elisabeth; Malachova, Alexandra; Nguyen, Nhung Thi; Lorenz, Cindy; Haltrich, Dietmar; Berthiller, Franz; Adam, Gerhard

    2015-08-01

    Glycosylation plays a central role in plant defense against xenobiotics, including mycotoxins. Glucoconjugates of Fusarium toxins, such as deoxynivalenol-3-O-?-d-glucoside (DON-3G), often cooccur with their parental toxins in cereal-based food and feed. To date, only limited information exists on the occurrence of glucosylated mycotoxins and their toxicological relevance. Due to a lack of analytical standards and the requirement of high-end analytical instrumentation for their direct determination, hydrolytic cleavage of ?-glucosides followed by analysis of the released parental toxins has been proposed as an indirect determination approach. This study compares the abilities of several fungal and recombinant bacterial ?-glucosidases to hydrolyze the model analyte DON-3G. Furthermore, substrate specificities of two fungal and two bacterial (Lactobacillus brevis and Bifidobacterium adolescentis) glycoside hydrolase family 3 ?-glucosidases were evaluated on a broader range of substrates. The purified recombinant enzyme from B. adolescentis (BaBgl) displayed high flexibility in substrate specificity and exerted the highest hydrolytic activity toward 3-O-?-d-glucosides of the trichothecenes deoxynivalenol (DON), nivalenol, and HT-2 toxin. A Km of 5.4 mM and a Vmax of 16 ?mol min(-1) mg(-1) were determined with DON-3G. Due to low product inhibition (DON and glucose) and sufficient activity in several extracts of cereal matrices, this enzyme has the potential to be used for indirect analyses of trichothecene-?-glucosides in cereal samples. PMID:25979885

  1. Detection of Type A Trichothecene Di-Glucosides Produced in Corn by High-Resolution Liquid Chromatography-Orbitrap Mass Spectrometry

    PubMed Central

    Nakagawa, Hiroyuki; Sakamoto, Shigeru; Sago, Yuki; Nagashima, Hitoshi

    2013-01-01

    The existence of di-glucosylated derivative of T-2 toxin in plant (corn powder) was confirmed for the first time in addition to that of HT-2 toxin. These masked mycotoxins (mycotoxin glucosides) were identified as T-2 toxin-di-glucoside (T2GlcGlc) and HT-2 toxin-di-glucoside (HT2GlcGlc) based on accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometric (LC-Orbitrap MS) analysis. Although the absolute structure of T2GlcGlc was not clarified, two glucose molecules were suggested to be conjugated at 3-OH position in tandem when considering the structure of T-2 toxin. On the other hand, the specification of the structure seems to be more complicated in the case of HT2GlcGlc, since HT-2 toxin has two possible positions (at 3-OH and 4-OH) to be glusocylated. In addition, 15-monoacetoxyscirpenol-glucoside (MASGlc) was also detected in the identical sample. PMID:23524332

  2. Fusarium redolens 6WBY3, an endophytic fungus isolated from Fritillaria unibracteata var. wabuensis, produces peimisine and imperialine-3?-d-glucoside.

    PubMed

    Pan, By Feng; Su, Xuemei; Hu, Bo; Yang, Nan; Chen, Que; Wu, Wei

    2015-06-01

    The major biological active ingredients of Bulbus Fritillariae cirrhosae (BFC) are steroidal alkaloids, such as peimisine, imperialine-3?-d-glucoside, and peimine. The bulbus of Fritillaria unibracteata var. wabuensis (FUW) was officially recorded in the National Pharmacopoeia of China (2010 edition) as one of the sources of BFC because of its positive therapeutic effects and few side effects. The endophytic fungus strain 6WBY3 was isolated from the fresh bulbus of FUW that had been cultivated for six years. Based on morphological methods and the phylogenetic analysis of internal transcribed spacer (ITS) sequences, this strain was identified as Fusarium redolens. Using color reaction analysis, high performance liquid chromatography with evaporative light scattering detection (HPLC-ELSD), and mass spectrometry (MS), it was demonstrated that F. redolens 6WBY3 could produce peimisine and imperialine-3?-d-glucoside, similar to its host plant. The yields of peimisine and imperialine-3?-d-glucoside were 16.0?g·l(-1) and 18.8?g·l(-1), respectively, in one week of culture. These results indicate that F. redolens 6WBY3 is a promising candidate for the large scale production of peimisine and imperialine-3?-d-glucoside. In addition, the results from the strain 6WBY3 lay the foundation for further study into the mechanism of Fritillaria alkaloids biosynthesis in fungi. PMID:25869849

  3. C-Glucoside xanthone from the stem bark extract of Bersama engleriana

    PubMed Central

    Djemgou, Pierre C.; Hussien, Taha A.; Hegazy, Mohamed-Elamir F.; Ngandeu, François; Neguim, Gilles; Tane, Pierre; Mohamed, Abou-El-Hamd H.

    2010-01-01

    Background: The genus Bersama belongs to the Melianthaceae family and comprises of four species (B. swinnyi, B. yangambiensis, B. abyssinica, and B. engleriana) all of which are very high trees; the latter two detected species are found in Cameroon. Previous phytochemical investigation on B. yangambiensis, B. swinnyi, and B. abyssinica led to the isolation of triterpenes, saponins, flavonoids, and xanthones. Method: The stem bark of B. engleriana were collected in the village, Baham near Bafoussam city, Cameroon in August 2003 and identifi ed by Dr. Onana National Herbaruim, Yaound?, Cameroon. The air dried and powdered stem bark of B. engleriana (1 kg) was extracted at room temperature with CH2Cl2-MeOH (1:1) 5 L for 48 hours. The mixture of the solvent was removed by evaporation to yield 200 g of crude extract. The latter was then dissolved in CH2Cl2 to give the CH2Cl2 soluble fraction of 5 g and a remaining gum of 195 g. Part of the remaining gum (22 g) was dissolved in water and extracted four times with butanol to give 12 g of red oil; which was then separated by paper chromatography, with butanol-acetic acid-water (4:1:5), to give 3 g of orange gum; purification was carried out on HPLC with MeOH (100%) to yield 2 g of mangiferin (1) as red oil. The CH2Cl2 soluble extract was eluted on silica gel n-hexane-CH2Cl2 gradient ratio and Sephadex LH-20 (n-hexane -CH2Cl2 -MeOH, (7:4:0.5) to afford compounds swinniol (2), ?4-stigmaster-3?-ol (3), 4-methylstigmaster-5,23-dien-3?-ol(4). Results: Herein, we carried out a phytochemical study of the stem bark of B. engleriana, and we report herein the isolation and structural elucidation of mangiferin, in addition to three triterpenes, previously reported from other species of the genus.[35] The assignment of the signals of mangiferin was determined using 1H, 13C-NMR, and 2D-NMR spectral data (HMQC, COSY, HMBC). The terpenoids were identifi ed by comparison of their 1H and 13C-NMR spectra with the literature data. Fractionation of the CH2Cl2-MeOH (1:1) extract of the stem bark of B. engleriana Guike gave mangiferin (1), in addition to three previously reported triterpenes, swinniol (2), ?4-stigmaster-3?-ol (3), and 4-methylstigmaster-5,23-dien-3-?-ol (4). Conclusions: A chemical investigation of the CH2Cl2-MeOH extract of the stem bark of Bersama engleriana afforded a xanthone C-glucoside (mangiferin) and fi rst isolation of three terpenoids from this species: swinniol (2), ?4-stigmaster-3?-ol (3), and 4-methylstigmaster-5,23-dien-3-?-ol (4). The complete 1H and 13C chemical shift assignments of mangiferin were determined using 1D and 2D NMR spectroscopic data (COSY, HMQC, HMBC, DEPT). The structures of the terpenoids were determined from their 1H and 13C NMR data and compared with the literature data. PMID:21808572

  4. Solubilization of functional plasma membrane-localized hepta-beta-glucoside elicitor-binding proteins from soybean.

    PubMed Central

    Cheong, J J; Alba, R; Côté, F; Enkerli, J; Hahn, M G

    1993-01-01

    Total membranes prepared from roots of soybean (Glycine max L.) seedlings have previously been shown to contain proteinaceous binding site(s) for a hepta-beta-glucoside elicitor of phytoalexin accumulation. The hepta-beta-glucoside elicitor-binding proteins have now been shown to co-migrate with a plasma membrane marker enzyme (vanadate-sensitive H(+)-ATPase) on linear sucrose density gradients. With the use of detergents, the elicitor-binding proteins have been solubilized in functional form from soybean root membranes. The nonionic detergents n-dodecylsucrose, n-dodecylmaltoside, and Triton X-114, at concentrations of 5 to 10 mg/mL, each solubilizes between 50 and 60% of the elicitor-binding activity in a single extraction of the membranes. A zwitterionic detergent, N-dodecyl-N,N-dimethyl-3-ammonio-1-propane-sulfonate (ZW 3-12), also solubilizes about 40% of the total binding activity at detergent concentrations between 1 and 2 mg/mL, but the total binding activity recovered is only approximately 50% of that recovered with the nonionic detergents. The elicitor-binding proteins solubilized with either n-dodecylsucrose or ZW 3-12 retain the high affinity for radiolabeled hepta-beta-glucoside elicitor (apparent dissociation constant [Kd] = 1.8 nM and 1.4 nM, respectively) that was observed with the membrane-localized binding proteins (apparent Kd = 1 nM). Competitive ligand-binding experiments with several structurally related synthetic oligoglucosides demonstrate that the solubilized binding proteins retain specificity for elicitor-active oligosaccharides, irrespective of the detergent used for solubilization. Moreover, the binding affinities of the oligoglucosides for the solubilized binding proteins correlate well with their abilities to induce phytoalexin accumulation in soybean cotyledon tissue. Gel-permeation chromatography of n-dodecylsucrose-solubilized elicitor-binding proteins demonstrate that the bulk of the elicitor-binding activity is associated with large detergent-protein micelles (relative molecular weight > 400,000). Our results suggest that n-dodecylsucrose is a suitable detergent for solubilizing elicitor-binding proteins from soybean root membranes with minimal losses of binding activity. More importantly, we demonstrate that solubilization does not significantly after the binding properties of the proteins for elicitor-active oligoglucosides. PMID:8290628

  5. Application of ESI/MS, CID/MS and tandem MS/MS to the fragmentation study of eriodictyol 7-O-glucosyl-(1-->2)-glucoside and luteolin 7-O-glucosyl-(1-->2)-glucoside

    NASA Astrophysics Data System (ADS)

    Es-Safi, Nour-Eddine; Kerhoas, Lucien; Einhorn, Jacques; Ducrot, Paul-Henri

    2005-12-01

    A mass spectrometric method based on the combined use of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry has been applied to the structural characterization of the eriodictyol 7-O-glucosyl-(1-->2)-glucoside and luteolin 7-O-glucosyl-(1-->2)-glucoside. The low-energy product ion mass spectrum of [M + H]+ and [M - H]- ions showed extensive fragmentation of the diglucose moiety, loss of the glycan residue, and fragmentation of the aglycon units that permit characterization of the interglycosidic linkage and the substituents in the A- and B-rings. Both glycosides were shown to yield the 0,2X00,2X1 ion which can be considered as characteristic of the 1-->2 interglycosidic linkage in the glucoglucoside adducts, since it can not be formed in the case of other interglycosidic types. In the case of the eriodictyol diglucoside the 1, 3 fragmentation of the C-ring was observed before those involving the carbohydrates thus allowing the position determination of the diglucoside moiety on the A-ring. In the negative ion mode only the luteolin diglucoside was shown to undergo collision-induced homolytic and heterolytic cleavages of the O-glycosidic bond producing the aglycone radical-anion [Y0-H]-- and Y0- product ions, while this was not observed in the case of eriodictyol glycoside. CID MS/MS analysis of the sodiated molecules gave complementary informations for the structural characterization of the studied compounds. The B2+ fragment which is useful for establishing that the terminal carbohydrate unit is linked to another carbohydrate and not directly to the aglycone was obtained as base peak. This result is of analytical value for the differentiation of O-diglycosyl and di-O-glycosyl flavonoids.

  6. Structures of eremophilane-type sesquiterpene glucosides, alticolosides A-G, from the Far Eastern endemic Ligularia alticola Worosch.

    PubMed

    Silchenko, Alexandra S; Kalinovsky, Anatoly I; Ponomarenko, Ludmila P; Avilov, Sergey A; Andryjaschenko, Pelageya V; Dmitrenok, Pavel S; Gorovoy, Peter G; Kim, Natalia Yu; Stonik, Valentin A

    2015-03-01

    Seven eremophilane-type sesquiterpene glucosides, alticolosides A-G, have been isolated from aerial parts of the endemic Far Eastern species Ligularia alticola Worosch. (Family Asteraceae) along with two known compounds, monoterpenoid glycoside (4S)-?-terpineol 8-O-?-D-glucopyranoside and norditerpenoid glycoside 7(8)-dihydro-?-ionone 3-O-?-D-glucopyranoside. Alticoloside D was identified with the earlier known 8-O-(?-D-glucopyranosyl)-2-oxo-eremophila-1(10),8,11-triene, but the stereostructure of the latter was revised on the basis of ROESY and CD data. All the glycosides are derivatives of new eremophilane-type aglycones, differing from known eremophilanes in details of planar and/or stereo structures except for the aglycone of alticoloside E. PMID:25481409

  7. A pre-clinical pharmacokinetic study in rats of three naturally occurring iridoid glycosides, Picroside-I, II and III, using a validated simultaneous HPLC-MS/MS assay.

    PubMed

    Zhu, Jianwei; Xue, Bingyang; Ma, Bo; Zhang, Qi; Liu, Ming; Liu, Lei; Yao, Di; Qi, Huanhuan; Wang, Yonglu; Ying, Hanjie; Wu, Zimei

    2015-07-01

    A selective and sensitive high-performance liquid chromatography-electro-spray ionization tandem mass spectrometry (LC-ESI-MS/MS) method was developed for the simultaneous quantitative determination of Picroside-I, II, and III in rat plasma and tissue homogenate to aid the pre-clinical studies. The chromatographic separation was performed on a Hypersil GOLD AQ C18 column using a gradient elution program with a mobile phase consisting of 2mM ammonium acetate and acetonitrile. The detection was achieved using a triple quadrupole tandem MS in negative ionization multiple reaction monitoring (MRM) mode. One-step protein precipitation was selected for plasma and tissue sample preparation while liquid-liquid extraction failed to achieve satisfactory recoveries. The calibration curves of all three analytes in either plasma or tissue homogenate showed good linearity over the concentration range of 0.5-500ng/mL with a limit of quantitation at 0.5ng/mL. Both the intra- and inter-day accuracy and precision were within ±10%. The extraction recoveries were >70%, and the relative matrix effect ranged from 80.4% to 107.4% in all the biological samples. All the analytes were stable in matrices for at least 24h at room temperature, or 21 days in frozen. Three freeze/thaw cycles did not cause degradation. The method was successfully applied for quantification of the three iridoid glycosides in the collected plasma and various tissues following intravenous administration in rats. Picroside-I, II, and III were all eliminated rapidly with large volume of distribution. Among the three glycosides, Picroside-II showed the highest liver uptake, and only Picroside-I and II were found to get across the blood brain barrier (BBB). These results were consistent with their hepatoprotective or neuroprotective effects reported clinically. With the aid of the efficient and reliable simultaneous LC-ESI-MS/MS assay this pharmacokinetic study provided insights into their therapeutic targets of these three iridoid glycosides as well as valuable experimental basis for an expansion of their clinical indications. PMID:25984965

  8. Identification of cyanidin 3-O-?-(6?-(3-hydroxy-3-methylglutaroyl)glucoside) and other anthocyanins from wild and cultivated blackberries.

    PubMed

    Jordheim, Monica; Enerstvedt, Kjersti Hasle; Andersen, Oyvind M

    2011-07-13

    Anthocyanins from blackberries are natural dietary pigments. The aim of this study was to investigate the occurrence of anthocyanins in fruits of wild Norwegian blackberries and three blackberry ( Rubus fruticosus L.) cultivars and to report the complete identification of cyanidin 3-O-?-(6?-(3-hydroxy-3-methylglutaroyl)glucopyranoside), 5. This new pigment is most probably the same pigment that has previously been reported to occur in various blackberry samples as cyanidin 3-dioxalylglucoside. All of the examined blackberry samples contained in similar relative proportions the 3-glucoside (1), 3-rutinoside (2), 3-xyloside (3), and 3-O-?-(6?-malonylglucoside) (4) of cyanidin and 5. The absolute amounts of 1-5 in the wild Norwegian blackberries were 249, 18, 10, 24, and 22 mg of cyanidin 3-glucoside equivalents/100 g of fresh weight, respectively. PMID:21635009

  9. Pteroside A2--a new illudane-type sesquiterpene glucoside from pteridium caudatum L. Maxon, and the spectrometric characterization of caudatodienone.

    PubMed

    Castillo, Uvidelio F; Wilkins, Alistair L; Lauren, Denis R; Smith, Barry L; Alonso-Amelot, Miguel

    2003-04-23

    Fractionation of an extract of Pteridium caudatum L. Maxon. (syn P. aquilinum L. Kuhn var. caudatum) which had earlier yielded the illudane-type sesquiterpene glucosides, ptaquiloside (1a), isoptaquiloside (1b), and caudatoside (1c) afforded a mixture containing 1a and two minor components. Preparative HPLC afforded ptaquiloside Z (1d) and a new pteroside glucoside (pteroside A2) (3e), which was identified using a combination of mass spectral and one- and two-dimensional NMR analyses. The (1)H and (13)C NMR and mass spectrometric characterization of caudatodienone (2b), an unstable dienone derived from the degradation of caudatoside (1c) in pyridine solution, and the GC-MS characterization of some pterosin-type degradation products produced by reacting this solution with cosolvents is also reported. PMID:12696937

  10. Effects of electrode materials on the degradation, spectral characteristics, visual colour, and antioxidant capacity of cyanidin-3-glucoside and cyanidin-3-sophoroside during pulsed electric field (PEF) treatment

    Microsoft Academic Search

    Jianxia Sun; Weibin Bai; Yan Zhang; Xiaojun Liao; Xiaosong Hu

    2011-01-01

    The effects of three electrode materials – stainless steel (SS), pure titanium (PT), and titanium-based alloy (TA) – on the PEF-induced degradation, spectral characteristics, visual colour, and antioxidant capacity of cyanidin-3-glucoside (Cy-3-glc) and cyanidin-3-sophoroside (Cy-3-soph) were studied. Cy-3-glc and Cy-3-soph were degraded by PEF; SS retained Cy-3-glc and Cy-3-soph the most, while PT and TA led to greater degradation. Cy-3-glc

  11. Attempt to synthesize 2,3,5,4'-tetrahydroxystilbene derived from 2,3,5,4'-tetrahydroxystilbene-2-O-?-glucoside (THSG).

    PubMed

    Tamura, Masafumi; Koshibe, Yuhei; Kaji, Kiho; Ueda, Jun-Ya; Shirataki, Yoshiaki

    2015-01-01

    An attempt to synthesize aglycone 1 derived from 2,3,5,4'-tetrahydroxystilbene-2-O-?-glucoside (THSG) via the Wittig reaction and Mizoroki-Heck reaction is described. In the Wittig protocol, 2,3,5,4'-tetramethoxystilbene 2 was obtained. Additionally, a palladium-catalyzed Mizoroki-Heck reaction strategy yielded 2-aryl-2,3-dihydrobenzofuran 13 instead of derivative 12 in good yield. PMID:25475833

  12. Identification, properties, and genetic control of UDP-glucose: Cyanidin3-rhamnosyl-(1?6)-glucoside-5- O -glucosyltransferase isolated from petals of the red campion (Silene dioica)

    Microsoft Academic Search

    John Kamsteeg; Jan van Brederode; Gerrit van Nigtevecht

    1978-01-01

    An enzyme catalyzing the transfer of the glucosyl moiety of UDP-glucose to the 5-hydroxyl group of cyanidin-3-rhamnosyl-(1?6)-glucoside has been demonstrated in petal extracts of Silene dioica plants. This glucosyltransferase activity was not detectable in green parts of these plants. The enzyme activity is controlled by a single dominant gene M; no glucosyltransferase activity could be demonstrated in petals of m\\/m

  13. Determination of flavone C-glucosides in antioxidant of bamboo leaves (AOB) fortified foods by reversed-phase high-performance liquid chromatography with ultraviolet diode array detection

    Microsoft Academic Search

    Yu Zhang; Bili Bao; Boyi Lu; Yiping Ren; Xiaowei Tie; Ying Zhang

    2005-01-01

    Reversed-phase high-performance liquid chromatography (RP-HPLC) with ultraviolet diode array detection (UV-DAD) was used for the simultaneous determination of four flavone C-glucosides, i.e. orientin, homoorientin, vitexin and isovitexin in several food systems fortified by the antioxidant of bamboo leaves (AOB), such as high temperature sterilized milk, sunflower seed oil and extruded rice cake for the first time. The method included extraction

  14. ortho-Substituted C-aryl glucosides as highly potent and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors

    Microsoft Academic Search

    Baihua Xu; Yan Feng; Binhua Lv; Ge Xu; Lili Zhang; Jiyan Du; Kun Peng; Min Xu; Jiajia Dong; Wenbin Zhang; Ting Zhang; Liangcheng Zhu; Haifeng Ding; Zelin Sheng; Ajith Welihinda; Brian Seed; Yuanwei Chen

    2010-01-01

    A series of 2-substituted C-aryl glucosides have been synthesized and evaluated for inhibition of hSGLT1 and hSGLT2. Introduction of an appropriate ortho substituent at the proximal phenyl ring adjacent to the glycosidic bond was found to improve SGLT2 inhibitory activity and dramatically increase selectivity for hSGLT2 over hSGLT1. Selected compounds were investigated for in vivo efficacy.

  15. A flavonoid 3-O-glucoside:2?-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana

    PubMed Central

    Yonekura-Sakakibara, Keiko; Nakabayashi, Ryo; Sugawara, Satoko; Tohge, Takayuki; Ito, Takuya; Koyanagi, Misuzu; Kitajima, Mariko; Takayama, Hiromitsu; Saito, Kazuki

    2014-01-01

    Flavonol 3-O-diglucosides with a 1?2 inter-glycosidic linkage are representative pollen-specific flavonols that are widely distributed in plants, but their biosynthetic genes and physiological roles are not well understood. Flavonoid analysis of four Arabidopsis floral organs (pistils, stamens, petals and calyxes) and flowers of wild-type and male sterility 1 (ms1) mutants, which are defective in normal development of pollen and tapetum, showed that kaempferol/quercetin 3-O-?-d-glucopyranosyl-(1?2)-?-d-glucopyranosides accumulated in Arabidopsis pollen. Microarray data using wild-type and ms1 mutants, gene expression patterns in various organs, and phylogenetic analysis of UDP-glycosyltransferases (UGTs) suggest that UGT79B6 (At5g54010) is a key modification enzyme for determining pollen-specific flavonol structure. Kaempferol and quercetin 3-O-glucosyl-(1?2)-glucosides were absent from two independent ugt79b6 knockout mutants. Transgenic ugt79b6 mutant lines transformed with the genomic UGT79B6 gene had the same flavonoid profile as wild-type plants. Recombinant UGT79B6 protein converted kaempferol 3-O-glucoside to kaempferol 3-O-glucosyl-(1?2)-glucoside. UGT79B6 recognized 3-O-glucosylated/galactosylated anthocyanins/flavonols but not 3,5- or 3,7-diglycosylated flavonoids, and prefers UDP-glucose, indicating that UGT79B6 encodes flavonoid 3-O-glucoside:2?-O-glucosyltransferase. A UGT79B6-GUS fusion showed that UGT79B6 was localized in tapetum cells and microspores of developing anthers. PMID:24916675

  16. Cyanidin3- O-?-glucoside inhibits iNOS and COX2 expression by inducing liver X receptor alpha activation in THP1 macrophages

    Microsoft Academic Search

    Qing Wang; Min Xia; Chi Liu; Honghui Guo; Qingyuan Ye; Yan Hu; Yinghui Zhang; Mengjun Hou; Huilian Zhu; Jing Ma; Wenhua Ling

    2008-01-01

    Anthocyanins belong to a large and widespread group of water-soluble phytochemicals and exhibit potent antioxidative and anti-inflammatory properties; however, the molecular mechanisms of these biochemical actions mediated by anthocyanins remain unclear. In this study, our data show that pretreatment of THP-1 macrophages with Cyanidin-3-O-?-glucoside (C3G) for 12 h can enhance the expression and transcriptional activities of the nuclear receptor peroxisome proliferator-activated

  17. Differential cell-protective function of two resveratrol (trans-3,5,4'-trihydroxystilbene) glucosides against oxidative stress.

    PubMed

    Hosoda, Ryusuke; Kuno, Atsushi; Hori, Yusuke S; Ohtani, Katsuki; Wakamiya, Nobutaka; Oohiro, Azusa; Hamada, Hiroki; Horio, Yoshiyuki

    2013-01-01

    Resveratrol (trans-3,5,4'-trihydroxystilbene; RSV), a natural polyphenol, exerts a beneficial effect on health and diseases. RSV targets and activates the NAD(+)-dependent protein deacetylase SIRT1; in turn, SIRT1 induces an intracellular antioxidative mechanism by inducing mitochondrial superoxide dismutase (SOD2). Most RSV found in plants is glycosylated, and the effect of these glycosylated forms on SIRT1 has not been studied. In this study, we compared the effects of RSV and two glycosyl RSVs, resveratrol-3-O-?-d-glucoside (3G-RSV; polydatin/piceid) and resveratrol-4'-O-?-d-glucoside (4'G-RSV), at the cellular level. In oxygen radical absorbance capacity and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, the antioxidant activity of 3G-RSV was comparable to that of RSV, whereas the radical-scavenging efficiency of 4'G-RSV was less than 50% of that of RSV. However, 4'G-RSV, but not 3G-RSV, induced SIRT1-dependent histone H3 deacetylation and SOD2 expression in mouse C2C12 skeletal myoblasts; as with RSV, SIRT1 knockdown blunted these effects. RSV and 4'G-RSV, but not 3G-RSV, mitigated oxidative stress-induced cell death in C2C12 cells and primary neonatal rat cardiomyocytes. RSV and 4'G-RSV inhibited C2C12 cell proliferation, but 3G-RSV did not. RSV was found in both the intracellular and extracellular fractions of C2C12 cells that had been incubated with 4'G-RSV, indicating that 4'G-RSV was extracellularly deglycosylated to RSV, which was then taken up by the cells. C2C12 cells did not deglycosylate 3G-RSV. Our results point to 4'G-RSV as a useful RSV prodrug with high water solubility. These data also show that the in vitro antioxidative activity of these molecules did not correlate with their ability to protect cells from oxidative stress-induced apoptosis. PMID:23042952

  18. Enhanced catalytic efficiency in quercetin-4'-glucoside hydrolysis of Thermotoga maritima ?-glucosidase A by site-directed mutagenesis.

    PubMed

    Sun, Huihui; Xue, Yemin; Lin, Yufei

    2014-07-16

    Te-BglA and Tm-BglA are glycoside hydrolase family 1 ?-glucosidases from Thermoanaerobacter ethanolicus JW200 and Thermotoga maritima, respectively, with 53% sequence identity. However, Te-BglA could more effectively hydrolyze isoflavone glucosides to their aglycones than could Tm-BglA, possibly due to the difference in amino acid residues around their glycone binding pockets. Site-directed mutagenesis was used to replace the amino acid residues of Tm-BglA with the corresponding residues of Te-BglA, generating three single mutants (F221L, N223L, and G224T), as well as the corresponding three double mutants (F221L/N223L, F221L/G224T, and N223L/G224T) and one triple mutant (F221L/N223L/G224T). The seven mutants have been purified, characterized, and compared to the wild-type Tm-BglA. The effects of the mutations on kinetics, enzyme activity, and substrate specificity were determined. All mutants showed pH-activity curves narrower on the basic side and wider on the acid side and had similar optimal pH and stability at pH 6.5-8.3. They were more stable up to 85 °C, but G224T displayed higher optimal temperature than Tm-BglA. Seven mutants indicated an obvious increase in catalytic efficiency toward p-nitrophenyl ?-D-glucopyranoside (pNPG) but an increase or not change in K(m). All mutants showed a decrease in catalytic efficiency of isoflavonoid glycosides and were not changed for F221L and lost for N223L in enzymatic hydrolysis on quercetin glucosides. Contrarily, G224T resulted in a dramatic increase conversion of Q4' (35.5%) and Q3,4' (28.6%) in accord with an increased turnover number (k(cat), 1.4×) and catalytic efficiency (k(cat)/K(m), 2.2×) as well as a decrease in K(m) (0.24) for Q4'. Modeling showed that G224T mutation at position 224 may enhance the interaction between G224T and 5-OH and 3-OH on the quercetin backbone of Q4'. PMID:24933681

  19. Tetrahydroxystilbene glucoside improves TNF-?-induced endothelial dysfunction: involvement of TGF?/Smad pathway and inhibition of vimentin expression.

    PubMed

    Yao, Wenjuan; Gu, Chengjing; Shao, Haoran; Meng, Guoliang; Wang, Huiming; Jing, Xiang; Zhang, Wei

    2015-01-01

    Endothelial dysfunction plays an important role in the pathogenesis of atherogenesis. 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component of the rhizome extract from Polygonum multiflorum (PM), exhibits significant anti-atherosclerotic activity. Here, we used human umbilical vein endothelial cells (HUVECs) induced by tumor necrosis factor-? (TNF-?) in vitro to investigate the cytoprotective effects of TSG on TNF-?-induced endothelial injury and the related mechanisms. Pretreatment with 50 and 100 ?M TSG markedly attenuated TNF-?-induced loss of cell viability and release of lactate dehydrogenase (LDH) and inhibited TNF-?-induced cell apoptosis. The inhibition of vimentin expression was involved in the cytoprotection afforded by TSG. Using inhibitors for PI3K and TGF? or siRNA for Akt and Smad2, we found that vimentin production in HUVECs is regulated by TGF?/Smad signaling, but not by PI3K-Akt-mTOR signaling. Meanwhile, TSG inhibited both the expression of TGF?1 and the phosphorylation of Smad2 and Smad3, and TSG suppressed the nuclear translocation of Smad4 induced by TNF-?. These results suggest that TSG protects HUVECs against TNF-?-induced cell damage by inhibiting vimentin expression via the interruption of the TGF?/Smad signaling pathway. PMID:25571766

  20. A natural flavonoid glucoside icariin inhibits Th1 and Th17 cell differentiation and ameliorates experimental autoimmune encephalomyelitis.

    PubMed

    Shen, Ruile; Deng, Wenjing; Li, Chun; Zeng, Guangwei

    2015-02-01

    Multiple sclerosis (MS) is an autoimmune disease that is characterized by recurrent episodes of T cell-mediated immune attack on central nervous system (CNS) myelin, leading to axon damage and progressive disability. Icariin, a natural flavonoid glucoside isolated from plants in the Epimedium family, has been proved to have various pharmacological activities. However, the effect of icariin on experimental autoimmune encephalomyelitis (EAE) has never been investigated. In our current study, we found that icariin treatment leads to alleviated inflammatory infiltration and reduced blood-brain barrier leakage (BBB) of the paracellular tracer (FITC-dextran) in EAE. Mice that received icariin-treated T cells also displayed lower EAE scores and better clinical recovery from EAE. Icariin administration suppresses the frequencies of Th1 and Th17 cells in the splenocytes and lymph node cells. Icariin-treated mice also show lower frequency of Th17 cells in CNS mononuclear cells. The effect of icariin on Th1 and Th17 cell differentiation may be mediated via modulation of dendritic cells (DCs). Furthermore, icariin suppresses the proliferation of T cells and the differentiation of Th1 and Th17 cells in vitro. In conclusion, icariin ameliorates EAE and this was associated with suppressed Th1 and Th17 cell differentiation. PMID:25528476

  1. Stilbene glucoside from Polygonum multiflorum Thunb.: a novel natural inhibitor of advanced glycation end product formation by trapping of methylglyoxal.

    PubMed

    Lv, Lishuang; Shao, Xi; Wang, Liyan; Huang, Derong; Ho, Chi-Tang; Sang, Shengmin

    2010-02-24

    Methylglyoxal (MGO), the reactive dicarbonyl intermediate generated during the nonenzymatic glycation between reducing sugars and amino groups of proteins, lipids, and DNA, is the precursor of advanced glycation end products (AGEs). Many studies have shown that AGEs play a major pathogenic role in diabetes and its complications. This study found that 2,3,5,4'-tetrahydroxystilbene 2-O-beta-D-glucoside (THSG), the major bioactive compound from Polygonum multiflorum Thunb., can efficiently inhibit the formation of AGEs in a dose-dependent manner by trapping reactive MGO under physiological conditions (pH 7.4, 37 degrees C). More than 60% MGO was trapped by THSG within 24 h, which was much more effective than resveratrol and its methylated derivative, pterostilbene, the two major bioactive dietary stilbenes. The major mono- and di-MGO adducts of THSG were successfully purified and found to be mixtures of tautomers. LC-MS and NMR data showed that positions 4 and 6 of the A ring were the major active sites for trapping MGO. It was also found that THSG could significantly inhibit the formation of AGEs in the human serum albumin (HSA)-MGO assay and both mono- and di-MGO adducts of THSG were detected in this assay using LC-MS. The results suggest that the ability of THSG to trap reactive dicarbonyl species makes it a potential natural inhibitor of AGEs. PMID:20104848

  2. Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death.

    PubMed

    Murthy, Kotamballi N Chidambara; Jayaprakasha, Guddadarangavvanahally K; Patil, Bhimanagouda S

    2015-03-01

    Obacunone and obacunone glucoside (OG) are naturally occurring triterpenoids commonly found in citrus and other plants of the Rutaceae family. The current study reports the mechanism of cytotoxicity of citrus-derived obacunone and OG on human androgen-dependent prostate cancer LNCaP cells. Both limonoids exhibited time- and dose-dependent inhibition of cell proliferation, with more than 60% inhibition of cell viability at 100 ?M, after 24 and 48 h. Analysis of fragmentation of DNA, activity of caspase-3, and cytosolic cytochrome-c in the cells treated with limonoids provided evidence for activation of programmed cell death by limonoids. Treatment of LNCaP cells with obacunone and OG resulted in dose-dependent changes in expression of proteins responsible for the induction of programmed cell death through the intrinsic pathway and down-regulation of Akt, a key molecule in cell signaling pathways. In addition, obacunone and OG also negatively regulated an inflammation-associated transcription factor, androgen receptor, and prostate-specific antigen, and activated proteins related to the cell cycle, confirming the ability of limonoids to induce cytotoxicity through multiple pathways. The results of this study provided, for the first time, an evidence of the cytotoxicity of obacunone and OG in androgen-dependent human prostate cancer cells. PMID:25592883

  3. Plant Food Delphinidin-3-Glucoside Significantly Inhibits Platelet Activation and Thrombosis: Novel Protective Roles against Cardiovascular Diseases

    PubMed Central

    Yang, Yan; Shi, Zhenyin; Reheman, Adili; Jin, Joseph W.; Li, Conglei; Wang, Yiming; Andrews, Marc C.; Chen, Pingguo; Zhu, Guangheng; Ling, Wenhua; Ni, Heyu

    2012-01-01

    Delphinidin-3-glucoside (Dp-3-g) is one of the predominant bioactive compounds of anthocyanins in many plant foods. Although several anthocyanin compounds have been reported to be protective against cardiovascular diseases (CVDs), the direct effect of anthocyanins on platelets, the key players in atherothrombosis, has not been studied. The roles of Dp-3-g in platelet function are completely unknown. The present study investigated the effects of Dp-3-g on platelet activation and several thrombosis models in vitro and in vivo. We found that Dp-3-g significantly inhibited human and murine platelet aggregation in both platelet-rich plasma and purified platelets. It also markedly reduced thrombus growth in human and murine blood in perfusion chambers at both low and high shear rates. Using intravital microscopy, we observed that Dp-3-g decreased platelet deposition, destabilized thrombi, and prolonged the time required for vessel occlusion. Dp-3-g also significantly inhibited thrombus growth in a carotid artery thrombosis model. To elucidate the mechanisms, we examined platelet activation markers via flow cytometry and found that Dp-3-g significantly inhibited the expression of P-selectin, CD63, CD40L, which reflect platelet ?- and ?-granule release, and cytosol protein secretion, respectively. We further demonstrated that Dp-3-g downregulated the expression of active integrin ?IIb?3 on platelets, and attenuated fibrinogen binding to platelets following agonist treatment, without interfering with the direct interaction between fibrinogen and integrin ?IIb?3. We found that Dp-3-g reduced phosphorylation of adenosine monophosphate-activated protein kinase, which may contribute to the observed inhibitory effects on platelet activation. Thus, Dp-3-g significantly inhibits platelet activation and attenuates thrombus growth at both arterial and venous shear stresses, which likely contributes to its protective roles against thrombosis and CVDs. PMID:22624015

  4. Deglycosylation is a key step in biotransformation and lifespan effects of quercetin-3-O-glucoside in Caenorhabditis elegans.

    PubMed

    Dueñas, Montserrat; Surco-Laos, Felipe; González-Manzano, Susana; González-Paramás, Ana M; Gómez-Orte, Eva; Cabello, Juan; Santos-Buelga, Celestino

    2013-10-01

    Due to their purported healthful activities, quercetin and other flavonoids are being increasingly proposed as nutraceuticals. Quercetin occurs in food as glycosides; however, most assays on its activity have been performed with the aglycone, despite glycosylation deeply affects compound bioavailability. In this work, the uptake and lifespan effects of quercetin-3-O-glucoside (Q3Glc) and quercetin have been assessed in Caenorhabditis elegans. Q3Glc was taken up by this nematode in a concentration-dependent manner and rapidly deglycosylated to quercetin, which was accumulated in the worm and partially biotransformed to conjugated metabolites. Significant mean lifespan extension up to 23% compared to controls was observed in wild type worms cultivated in the presence of low concentrations of Q3Glc (10 ?M and 25 ?M), whereas exposure to greater concentrations of Q3Glc (50-200 ?M) caused a reduction in mean and maximum lifespan compared with the control. By contrast, treatment of klo-1 and klo-2 mutant worms lacking ?-glucosidase activity with 200 ?M of Q3Glc led to extended mean lifespan (up to 39%), similar to quercetin aglycone at the same concentration levels. In those mutants, Q3Glc was accumulated without important deglycosylation to quercetin was produced. Taken together, these findings indicated that Q3Glc was taken up by the nematode in greater extent than quercetin, and that deglycosylation and subsequent aglycone accumulation in the worm appeared as key points to explain the observed lifespan effects. The obtained results also suggested that facilitated absorption should be more important for the uptake of quercetin derivatives than passive diffusion. PMID:23856528

  5. Dissimilar Mechanisms of Cytochrome c Release Induced by Octyl Glucoside-Activated BAX and by BAX Activated with Truncated BID

    PubMed Central

    Li, Tsyregma; Brustovetsky, Tatiana; Antonsson, Bruno; Brustovetsky, Nickolay

    2009-01-01

    SUMMARY In the present study, we compared alkali-resistant BAX insertion into the outer mitochondrial membrane, mitochondrial remodeling, mitochondrial membrane potential changes, and cytochrome c (Cyt c) release from isolated brain mitochondria triggered by recombinant BAX oligomerized with 1% octyl glucoside (BAXoligo) and by a combination of monomeric BAX (BAXmono) and caspase 8-cleaved C-terminal fragment of recombinant BID (truncated BID, tcBID). We also examined whether the effects induced by BAXoligo or by BAXmono activated with tcBID depended on induction of the mitochondrial permeability transition. The results obtained in this study revealed that tcBID plus BAXmono produced BAX insertion and Cyt c release without overt changes in mitochondrial morphology. On the contrary, treatment of mitochondria with BAXoligo resulted in BAX insertion and Cyt c release, which were accompanied by gross distortion of mitochondrial morphology. The effects of BAXoligo could be at least partially suppressed by mitochondrial depolarization. The effects of tcBID plus BAXmono were insensitive to depolarization. BAXoligo produced similar BAX insertion, mitochondrial remodeling, and Cyt c release in KCl? and in N-methyl-D-glucamine-based incubation media indicating a non-essential role for K+ influx into mitochondria in these processes. A combination of cyclosporin A and ADP, inhibitors of the mitochondrial permeability transition, attenuated Cyt c release, mitochondrial remodeling, and depolarization induced by BAXoligo, but failed to influence the effects produced by tcBID plus BAXmono. Thus, our results suggest a significant difference in the mechanisms of the outer mitochondrial membrane permeabilization and Cyt c release induced by detergent-oligomerized BAXoligo and by BAX activated with tcBID. PMID:19664589

  6. Cyanidin-3-O-?-glucoside ameliorates lipopolysaccharide-induced acute lung injury by reducing TLR4 recruitment into lipid rafts.

    PubMed

    Fu, Yunhe; Zhou, Ershun; Wei, Zhengkai; Wang, Wei; Wang, Tiancheng; Yang, Zhengtao; Zhang, Naisheng

    2014-07-15

    Cyanidin-3-O-?-glucoside (C3G), a typical anthocyanin pigment that exists in the human diet, has been reported to have anti-inflammatory properties. The aim of this study was to detect the effect of C3G on LPS-induced acute lung injury and to investigate the molecular mechanisms. Acute lung injury was induced by intratracheal administration of LPS in mice. Alveolar macrophages from mice were stimulated with LPS and were treated with C3G. Our results showed that C3G attenuated lung histopathologic changes, myeloperoxidase (MPO) activity, TNF-?, IL-1? and IL-6 production in LPS-induced acute lung injury model. In vitro, C3G dose-dependently inhibited TNF-?, IL-1?, IL-6, IL-10 and IFN-? production, as well as NF-?B and IRF3 activation in LPS-stimulated alveolar macrophages. Furthermore, C3G disrupted the formation of lipid rafts by depleting cholesterol and inhibited TLR4 translocation into lipid rafts. Moreover, C3G activated LXR?-ABCG1-dependent cholesterol efflux. Knockout of LXR? abrogated the anti-inflammatory effects of C3G. In conclusion, C3G has a protective effect on LPS-induced acute lung injury. The promising anti-inflammatory mechanisms of C3G is associated with up-regulation of the LXR?-ABCG1 pathway which result in disrupting lipid rafts by depleting cholesterol and reducing translocation of TLR4 to lipid rafts, thereby suppressing TLR4 mediated inflammatory response. PMID:24841888

  7. Molecular dynamics simulations of the lyotropic reverse hexagonal (HII) of Guerbet branched-chain ?-D-glucoside.

    PubMed

    Nguan, Hockseng; Ahmadi, Sara; Hashim, Rauzah

    2014-01-01

    Through atomistic molecular dynamic simulations using a GROMOS53a6 force field for the carbohydrate, we studied the lyotropic reverse hexagonal phase HII from a glycolipid, namely the Guerbet branched-chain ?-d-glucoside, at 14% and 22% water concentrations. Our simulations showed that at low water concentration (14%) the sugar head group overlapped extensively and protruded into the water channel. In contrast, in the 22% concentration system a water column free from the sugar headgroup ('free' water) was formed as expected for the system close to the limit of maximum hydration. In both concentrations, we found anomalous water diffusion in the xy-plane, i.e. the two-dimensional space confined by the surface of the cylinder. On the other hand, along the z-axis, the water diffusion obeyed the Einstein relation for the 22% system, while for the 14% system it was slightly anomalous. For the 22% system, the diffusion along the z-axis of the 'free' water obeyed the Einstein relation, while that of the 'bound' water is slightly anomalous. The xy-plane displacement of the 'bound' water was higher than that for the 'free' water at times longer than 200 ps, as a consequence of the exchange of water molecules between the two regions. Based on our findings, we proposed an alternative explanation to the observed spatial heterogeneity in the HII phase from probe diffusion by Penaloza et al. (Phys. Chem. Chem. Phys., 2012, 14(15), 5247-5250). We found the extent of contact with water was different at different oxygen atoms within the sugar ring. Generally, a higher probability of hydrogen bonding but a shorter lifetime was found in 22% water compared to the case of 14% water. Finally, we examined the extension and compression of the alkyl chain of a columnar. PMID:24257208

  8. A semiquinone glucoside derivative isolated from Bacillus sp. INM-1 provides protection against 5-fluorouracil-induced immunotoxicity.

    PubMed

    Mishra, Saurabh; Malhotra, Poonam; Gupta, Ashutosh K; Singh, Praveen K; Javed, Saleem; Kumar, Raj

    2015-01-01

    5-Fluorouracil (5-FU) is a widely used anti-cancer agent; however, it induces immunosuppression in patients undergoing a chemotherapy regime. The mode of action by which 5-FU induces immunosuppression is primarily via inhibition of hematopoietic growth factors. In the present study, immunoprotective effects of a semiquinone glucoside derivative (SQGD), a bacterial metabolite isolated from Bacillus sp. INM-1, were evaluated in a model of 5-FU-induced immunotoxicity in C57Bl/6 male mice. The evaluation was done by analyzing G-CSF, GM-CSF, and M-CSF expression in the serum, spleen, and bone marrow cells of the mice at different timepoints after 5-FU treatment. Mice received a single intraperitoneal injection of either 5-FU (75 mg/kg) alone, SQGD (50 mg/kg) alone, or SQGD 2 h prior to the 5-FU treatment. Control mice received saline vehicle only. The results demonstrated that 5-FU treatment significantly inhibited G-CSF, GM-CSF, and M-CSF expression in all three sites at all timepoints from 6-72 h post 5-FU. In SQGD treated mice, up-regulation of factor expression was observed in each compartment, and significantly so most often after 12 h. SQGD treatment prior to 5-FU administration to the mice significantly increased in all sites evaluated - relative to values in both control mice and 5-FU only-treated mice - G-CSF, M-CSF, and GM-CSF expression at almost every timepoint. The present findings suggest that SQGD provides protection against 5-FU-induced immunotoxicity in mice and could protect bone marrow progenitor cells against the effects of cytotoxic drugs used for treatment of cancer. The findings also suggested to us that SQGD is a potential immunomodulator and could protect hematopoiesis against toxic assault caused by anti-cancer drugs in the clinical setting. PMID:24512327

  9. Cytotoxic and EGFR tyrosine kinase inhibitory activities of aglycone derivatives obtained by enzymatic hydrolysis of oleoside-type secoiridoid glucosides, oleuropein and ligustroside

    Microsoft Academic Search

    Masafumi Kikuchi; Nariyasu Mano; Yoshimasa Uehara; Koichi Machida; Masao Kikuchi

    2011-01-01

    Hydrolysis of oleoside-type secoiridoid glucosides, oleuropein (1) and ligustroside (2), in the presence of ?-glucosidase provided their aglycones, named (5S,8R,9S)-7-3,4-dihydroxyphenethyl elenolate (3) and (5S,8R,9S)-7-4-hydroxyphenethyl elenolate (4), respectively. The structures of 3 and 4 were identified by spectroscopic means and optical rotation measurements. Evaluation of the cytotoxic and epidermal growth\\u000a factor receptor (EGFR) tyrosine kinase inhibitory activities of compounds 1–4 showed

  10. Cyanidin3- O -?-glucoside inhibits LPS-induced expression of inflammatory mediators through decreasing I?B? phosphorylation in THP1 cells

    Microsoft Academic Search

    Yinghui Zhang; Fuzhi Lian; Yanna Zhu; Min Xia; Qing Wang; Wenhua Ling; Xiang-Dong Wang

    2010-01-01

    Objective and design  As a common phytochemical, cyanidin 3-O-?-glucoside (C3G) has a role in inhibiting inflammatory mediators; however, its mechanism of action remains unclear. The\\u000a purpose of this study was to explore the effect of C3G on lipopolysaccharide (LPS)-stimulated TNF? and IL-6 expression in\\u000a the human monocyte\\/macrophage cell line THP-1, and to explore the mechanisms involved.\\u000a \\u000a \\u000a \\u000a \\u000a Methods  Differentiated THP-1 cells were treated

  11. Genetic transformation of Gentiana macrophylla with Agrobacterium rhizogenes: growth and production of secoiridoid glucoside gentiopicroside in transformed hairy root cultures.

    PubMed

    Tiwari, Rajesh Kumar; Trivedi, Mala; Guang, Zhang Chun; Guo, Guang-Qin; Zheng, Guo-Chang

    2007-02-01

    Hairy root cultures of Gentiana macrophylla were established by infecting the different explants four Agrobacterium rhizogenes strains namely A(4)GUS, R1000, LBA 9402 and ATCC11325, and hairy root lines were established with A. rhizogenes strain R1000 in 1/2 MS + B(5) medium. Initially, 42 independent hairy root clones were maintained and seven clones belongs to different category were evaluated for growth, morphology, integration and expression of Ri T-DNA genes, and alkaloid contents in dry root samples. On the basis of total root elongation, lateral root density and biomass accumulation on solid media, hairy root clones were separated into three categories. PCR and Southern hybridization analysis revealed both left and right T-DNA integration in the root clones and RT-PCR analysis confirmed the expression of hairy root inducible gene. GUS assay was also performed to confirm the integration of left T-DNA. The accumulation of considerable amounts of the root-specific secoiridoid glucosides gentiopicroside was observed in GM1 (T +/L and T +/R) and the GM2 (T +/L and T -/R DNA) type clones in considerably higher amount whether as two T -/L but T +/R callus-type clones (GM3) accumulated much less or only very negligible amounts of gentiopicroside. Out of four media composition the 1/2 MS + B(5) vitamin media was found most suitable. We found that initial establishment of root cultures largely depends on root:media ratio. Maximum growth rate was recorded in 1:50 root:media ratio. The maximum biomass in terms of fresh weight (33-fold) was achieved in 1/2 MS + B(5) media composition after 35 days in comparison to sixfold increase in control. The biomass increase was most abundant maximum from 15 to 30 days. Influence of A. rhizogenes strains and Ri plasmid of hairy root induction, the possible role of the T(L)-DNA and T(R)-DNA genes on growth pattern of hairy root, initial root inoculum:media ratio and effect of media composition is discussed. PMID:16972092

  12. Indonesian medicinal plants. X. Chemical structures of four new triterpene-glycosides, gongganosides D, E, F, and G, and two secoiridoid-glucosides from the bark of Bhesa paniculata (Celastraceae).

    PubMed

    Ohashi, K; Tanikawa, T; Okumura, Y; Kawazoe, K; Tatara, N; Minato, M; Shibuya, H; Kitagawa, I

    1994-09-01

    Four new triterpene-glycosides, named gongganosides D (4), E (5), F (6), and G (7), and two new secoiridoid-glucosides, (7R)-7-caffeoyloxysweroside (8) and (7S)-7-caffeoyloxysweroside (9), were isolated from the bark of the Indonesian medicinal plant Bhesa paniculata (Celastraceae). The chemical structures have been elucidated on the bases of their chemical and physiocochemical properties. PMID:7954929

  13. Halohydrins and polyols derived from antirrhinoside: structural revisions of muralioside and epimuralioside

    PubMed

    Franzyk; Jensen; Thale; Olsen

    1999-02-01

    Treatment of the iridoid glucoside antirrhinoside (1) with pyridinium chloride in dimethylformamide gave rise to the two possible trans-halohydrins, linarioside (4) and isolinarioside (5). Pyridinium bromide gave the two analogous bromohydrins. It is shown that the iridoid glucosides 8-epi-muralioside from Linaria arcusangeli and 7,8-epi-antirrhinoside from Linaria dalmatica are both identical with isolinarioside, and therefore, these names are redundant. The structure of muralioside isolated from Cymbalaria muralis is revised to that of its 8-epimer (8), while the structure of an isomeric, new iridoid glucoside from Paulownia tomentosa has been elucidated to be 7beta-hydroxyharpagide (3), the structure originally assigned to 8. In addition, 7alpha-hydroxyharpagide (2), the known product from the base-catalyzed hydrolytic opening of 1, has been isolated from Antirrhinum majus and thus shown to be a natural product. PMID:10075758

  14. ?-D-Glucoside utilization by Mycoplasma mycoides subsp. mycoides SC: possible involvement in the control of cytotoxicity towards bovine lung cells

    PubMed Central

    Vilei, Edy M; Correia, Ivone; Ferronha, M Helena; Bischof, Daniela F; Frey, Joachim

    2007-01-01

    Background Contagious bovine pleuropneumonia (CBPP) caused by Mycoplasma mycoides subsp. mycoides small-colony type (SC) is among the most serious threats for livestock producers in Africa. Glycerol metabolism-associated H2O2 production seems to play a crucial role in virulence of this mycoplasma. A wide number of attenuated strains of M. mycoides subsp. mycoides SC are currently used in Africa as live vaccines. Glycerol metabolism is not affected in these vaccine strains and therefore it does not seem to be the determinant of their attenuation. A non-synonymous single nucleotide polymorphism (SNP) in the bgl gene coding for the 6-phospho-?-glucosidase (Bgl) has been described recently. The SNP differentiates virulent African strains isolated from outbreaks with severe CBPP, which express the Bgl isoform Val204, from strains to be considered less virulent isolated from CBPP outbreaks with low mortality and vaccine strains, which express the Bgl isoform Ala204. Results Strains of M. mycoides subsp. mycoides SC considered virulent and possessing the Bgl isoform Val204, but not strains with the Bgl isoform Ala204, do trigger elevated levels of damage to embryonic bovine lung (EBL) cells upon incubation with the disaccharides (i.e., ?-D-glucosides) sucrose and lactose. However, strains expressing the Bgl isoform Val204 show a lower hydrolysing activity on the chromogenic substrate p-nitrophenyl-?-D-glucopyranoside (pNPbG) when compared to strains that possess the Bgl isoform Ala204. Defective activity of Bgl in M. mycoides subsp. mycoides SC does not lead to H2O2 production. Rather, the viability during addition of ?-D-glucosides in medium-free buffers is higher for strains harbouring the Bgl isoform Val204 than for those with the isoform Ala204. Conclusion Our results indicate that the studied SNP in the bgl gene is one possible cause of the difference in bacterial virulence among strains of M. mycoides subsp. mycoides SC. Bgl does not act as a direct virulence factor, but strains possessing the Bgl isoform Val204 with low hydrolysing activity are more prone to survive in environments that contain high levels of ?-D-glucosides, thus contributing in some extent to mycoplasmaemia. PMID:17439646

  15. C-Aryl Glucosides with Substituents at the Distal Aryl Ring as Sodium-Dependent Glucose Cotransporter Inhibitors for the Treatment of Diabetes Mellitus.

    PubMed

    Wang, Xuekun; Li, Ying; Yang, Baowei; Li, Zheng; Huang, Wenlong; Qian, Hai

    2015-08-01

    A series of novel C-aryl glucosides with various substituents at the distal aryl ring have been synthesized and evaluated for hypoglycemic effect in normal and diabetic mice and in type 2 diabetic rats. The results indicated that introduction of electron-donating group at the distal aryl ring could improve glucose tolerance in normal mice, whereas introduction of electron-withdrawing group at this position could deteriorate. The urinary glucose excretion was significantly increased after glucose (3 g/kg) administration in normal mice with the treatment of 13c. Moreover, compound 13c could reduce fed blood glucose levels in a dose-dependent manner in type 2 diabetic rats, showed a remarkable antihyperglycemic effect with 2 weeks of treatment in diabetic mice, and might be a promising drug candidate for the treatment of diabetes mellitus. PMID:25443983

  16. Higenamine 4'-O-?-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through ?2-adrenergic receptor.

    PubMed

    Kato, Eisuke; Inagaki, Yosuke; Kawabata, Jun

    2015-07-01

    Hypoglycemic effect is an efficient means to modulate elevated blood glucose levels in patients with diabetes. We found that the extract of lotus plumule (the germ of Nelumbo nucifera Gaertn. seed) showed potent glucose uptake enhancement activity against L6 myotubes, which results in a hypoglycemic effect. This activity was further investigated, and an active constituent was identified as a single bioactive compound, higenamine 4'-O-?-d-glucoside. Mechanistic studies employing phosphatidylinositol 3-kinase (PI3K) inhibitor, AMP-activated protein kinase (AMPK) inhibitor, or adrenergic receptor antagonist showed that the compound induced its activity through ?2-adrenergic receptor. Patients with type II diabetes mellitus frequently develop insulin resistance. Owing to the differences between the mechanism of action of insulin and of the isolated compound, the compound or lotus plumule itself may have the possibility of modulating blood glucose levels in insulin-resistant patients effectively. PMID:25943853

  17. Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata.

    PubMed

    Wang, Yang; Guan, Shu-Hong; Meng, Yu-Hui; Zhang, Yi-Bei; Cheng, Chun-Ru; Shi, Yang-Yang; Feng, Rui-Hong; Zeng, Feng; Wu, Zhi-Yuan; Zhang, Jing-Xian; Yang, Min; Liu, Xuan; Li, Qing; Chen, Xiao-Hui; Bi, Kai-Shun; Guo, De-An

    2013-10-01

    Eleven previously unknown compounds and 23 known compounds, including 20 phenanthrene or 9,10-dihydrophenanthrene derivatives, five bibenzyls, seven malate or tartrate benzyl ester glucosides, adenosine and gastrodin were isolated from tubers of Cremastra appendiculata. Among the obtained compounds, two are the first isolated dimers with one phenanthrene or bibenzyl unit connected to C-3 of 2,3,4,5-tetrahydro-phenanthro[2,1-b]furan moiety. In addition, 33 of these compounds were evaluated in vitro for their cytotoxic activity against two cancer cell lines. Among the compounds examined, one compound showed moderate cytotoxic activity, while five showed weak cytotoxic activity against the A549 cell line. PMID:23820314

  18. Phenylalanine ammonia lyase functions as a switch directly controlling the accumulation of calycosin and calycosin-7-O-beta-D-glucoside in Astragalus membranaceus var. mongholicus plants.

    PubMed

    Pan, Haiyun; Wang, Yuguo; Zhang, Yongfeng; Zhou, Tongshui; Fang, Changming; Nan, Peng; Wang, Xiaoqiang; Li, Xiaobing; Wei, Yinlong; Chen, Jiakuan

    2008-01-01

    Previously it had been shown that calycosin and calycosin-7-O-beta-D-glucoside (CGs) accumulate in whole plants, mainly in leaves, of Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao (A. mongholicus) plants in response to low temperature. In this work, it was demonstrated that the influences of different conditions on CGs biosynthesis, by examining the changes in CGs content, as well as the expression of related genes, including phenylalanine ammonia lyase (PAL1), cinnamic acid 4-hydroxylase (C4H), chalcone synthase (CHS), chalcone reductase (CHR), chalcone isomerase (CHI), isoflavone synthase (IFS), and isoflavone 3'-hydroxylase (I3'H). The seven gene mRNAs accumulated in leaves of A. mongholicus upon exposure to low temperature in a light-dependent manner, though they exhibited different expression patterns. Transcriptions of CHS, CHR, CHI, IFS, and I3'H of the calycosin-7-O-beta-D-glucoside pathway were all up-regulated when plants were transferred from 16 degrees C to 2 degrees C or 25 degrees C or from 2 degrees C (kept for 24 h) to 25 degrees C. However, fluctuations in temperature influenced differently the transcriptions of PAL1 and C4H of the general phenylpropanoid pathway in leaves. Moreover, the amount of PAL1 expression changed sharply up and down, consistent with the variation of the content of CGs. PAL enzyme activity appears to be the limiting factor in determining the CGs levels. The inhibitor of PAL enzyme, L-alpha-aminooxy-beta-phenylpropionic acid, almost entirely shut down CGs accumulation at low temperature. All these results confirmed that PAL1, as a smart gene switch, directly controls the accumulation of CGs in A. mongholicus plants, in a light-dependent manner, during low temperature treatment. PMID:18583351

  19. Discovery of the glycogen phosphorylase-modulating activity of a resveratrol glucoside by using a virtual screening protocol optimized for solvation effects.

    PubMed

    Mavrokefalos, Nikolaos; Myrianthopoulos, Vassilios; Chajistamatiou, Aikaterini S; Chrysina, Evangelia D; Mikros, Emmanuel

    2015-04-01

    The identification of natural products that can modulate blood glucose levels is of great interest as it can possibly facilitate the utilization of mild interventions such as herbal medicine or functional foods in the treatment of chronic diseases like diabetes. One of the established drug targets for antihyperglycemic therapy is glycogen phosphorylase. To evaluate the glycogen phosphorylase inhibitory properties of an in-house compound collection consisting to a large extent of natural products, a stepwise virtual and experimental screening protocol was devised and implemented. The fact that the active site of glycogen phosphorylase is highly hydrated emphasized that a methodological aspect needed to be efficiently addressed prior to an in silico evaluation of the compound collection. The effect of water molecules on docking calculations was regarded as a key parameter in terms of virtual screening protocol optimization. Statistical analysis of 125 structures of glycogen phosphorylase and solvent mapping focusing on the active site hydration motif in combination with a retrospective screening revealed the importance of a set of 29 crystallographic water molecules for achieving high enrichment as to the discrimination between active compounds and inactive decoys. The scaling of Van der Waals radii of system atoms had an additional effect on screening performance. Having optimized the in silico protocol, a prospective evaluation of the in-house compound collection derived a set of 18 top-ranked natural products that were subsequently evaluated in vitro for their activity as glycogen phosphorylase inhibitors. Two phenolic glucosides with glycogen phosphorylase-modulating activity were identified, whereas the most potent compound affording mid-micromolar inhibition was a glucosidic derivative of resveratrol, a stilbene well-known for its wide range of biological activities. Results show the possible phytotherapeutic and nutraceutical potential of products common in the Mediterranean countries, such as red wine and Vitis products in general or green raw salads and herbal preparations, where such compounds are abundant. PMID:25875507

  20. Cyanidin 3-glucoside attenuates obesity-associated insulin resistance and hepatic steatosis in high-fat diet-fed and db\\/db mice via the transcription factor FoxO1

    Microsoft Academic Search

    Honghui Guo; Min Xia; Tangbin Zou; Wenhua Ling; Ruimin Zhong; Weiguo Zhang

    Obesity is a major risk factor for the development of type 2 diabetes, and both conditions are now recognized to possess significant inflammatory components underlying their pathophysiologies. Here, we hypothesized that cyanidin 3-glucoside (C3G), a typical anthocyanin reported to possess potent anti-inflammatory properties, would ameliorate obesity-associated inflammation and metabolic disorders, such as insulin resistance and hepatic steatosis in mouse models

  1. Cyanidin 3-glucoside protects 3T3-L1 adipocytes against H 2O 2- or TNF-?-induced insulin resistance by inhibiting c-Jun NH 2-terminal kinase activation

    Microsoft Academic Search

    Honghui Guo; Wenhua Ling; Qing Wang; Chi Liu; Yan Hu; Min Xia

    2008-01-01

    Anthocyanins are naturally occurring plant pigments and exhibit an array of pharmacological properties. Our previous study showed that black rice pigment extract rich in anthocyanin prevents and ameliorates high-fructose-induced insulin resistance in rats. In present study, cyanidin 3-glucoside (Cy-3-G), a typical anthocyanin most abundant in black rice was used to examine its protective effect on insulin sensitivity in 3T3-L1 adipocytes

  2. Determination of cyanidin-3-glucoside (red kernel food colour) in beverages by high performance liquid chromatography and a study of its degradation by quadruple time-of-flight mass spectrometry

    Microsoft Academic Search

    Jia Song; Xiaolin Li; Lu Zeng; Hailing Liu; Mengxia Xie

    2011-01-01

    A method for the determination of cyanidin-3-glucoside (red kernel colour, RKC) in various matrices, including carbonated soft drinks, fruit-based soft drinks, sugar confectionery and milk-based drinks, by high performance liquid chromatography (HPLC) based on UV–Vis detection (at 520?nm) have been developed. Pre-treatment procedures for various matrices have been optimised. For soft drinks, the pH values were adjusted to 2.0, and

  3. Simultaneous determination of vitexin-4?- O-glucoside and vitexin-2?- O-rhamnoside from hawthorn leaves flavonoids in rat plasma by HPLC method and its application to pharmacokinetic studies

    Microsoft Academic Search

    Guo Ma; Xue-Hua Jiang; Zhuo Chen; Jing Ren; Chen-Rui Li; Tai-Ming Liu

    2007-01-01

    The present study was to investigate the pharmacokinetics of the two similar flavonoid glycosides, vitexin-4?-O-glucoside (VGL) and vitexin-2?-O-rhamnoside (VRH) in rats after intravenous administration of hawthorn leaves flavonoids (HLF). Blood samples were collected via tail vein at time intervals after drug administration and the plasma concentrations of the studied ingredients were analyzed by HPLC after the plasma protein was precipitated

  4. Simultaneous determination of vitexin-4?-O-glucoside, vitexin-2?-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma by UPLC–ESI-MS\\/MS

    Microsoft Academic Search

    Wenjun Zhang; Ming Xu; Chaoqun Yu; Guofeng Zhang; Xing Tang

    2010-01-01

    A sensitive and accurate ultra-performance liquid chromatography electrospray ionization tandem mass spectrometry (UPLC–ESI-MS\\/MS) method was developed and validated for the simultaneous determination of vitexin-4?-O-glucoside (VGL), vitexin-2?-O-rhamnoside (VRH), rutin (RUT) and vitexin (VIT) in rat plasma after intravenous administration of hawthorn leaves flavonoids (HLF). Following protein precipitation by methanol, the analytes were separated on an ACQUITY UPLC BEH C18 column packed

  5. C-Aryl glucosides substituted at the 4?-position as potent and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes

    Microsoft Academic Search

    Baihua Xu; Yan Feng; Huawei Cheng; Yanli Song; Binhua Lv; Yuelin Wu; Congna Wang; Shengbin Li; Min Xu; Jiyan Du; Kun Peng; Jiajia Dong; Wenbin Zhang; Ting Zhang; Liangcheng Zhu; Haifeng Ding; Zelin Sheng; Ajith Welihinda; Jacques Y. Roberge; Brian Seed; Yuanwei Chen

    2011-01-01

    A series of C-aryl glucosides with various substituents at the 4?-position of the distal aryl ring have been synthesized and evaluated for inhibition of hSGLT1 and hSGLT2. Introduction of alkyl or alkoxy substituents at the 4?-position was found to improve SGLT2 potency, whereas introduction of a hydrophilic group at this position was deleterious. Compounds with alkoxy-, cycloalkoxy- or cycloalkenyloxy-ethoxy scaffolds

  6. Malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase from scarlet sage (Salvia splendens) flowers. Enzyme purification, gene cloning, expression, and characterization.

    PubMed

    Suzuki, H; Nakayama, T; Yonekura-Sakakibara, K; Fukui, Y; Nakamura, N; Nakao, M; Tanaka, Y; Yamaguchi, M A; Kusumi, T; Nishino, T

    2001-12-28

    The orange to blue coloration of flowers in nature is, in most cases, provided by anthocyanins, a class of plant flavonoids, many of which are modified by malonyl group(s). However, the identity of the enzyme catalyzing the malonylation reaction remains to be established. Here, we describe for the first time the purification, characterization, and cDNA cloning of an anthocyanin malonyltransferase from scarlet sage (Salvia splendens) flowers. The purified enzyme (termed Ss5MaT1) was a monomeric 50-kDa protein catalyzing the regiospecific transfer of the malonyl group from malonyl-CoA to the 6"'-hydroxyl group of the 5-glucosyl moiety of anthocyanins. Ss5MaT1 showed a k(cat) value of 7.8 s(-1) at 30 degrees C and pH 7.0 for the malonylation of bisdemalonylsalvianin (pelargonidin 3-(6"-O-caffeyl-beta-glucopyranoside)-5-beta-glucopyranoside) and K(m) values of 101 microm and 57 microm for bisdemalonylsalvianin and malonyl-CoA, respectively. p-Coumaric acid, which mimics an aromatic acyl group linked to the 3-glucosidic moiety of an anthocyanin substrate, was a competitive inhibitor with respect to the substrate. This strongly suggests that the presence of an aromatic acyl group at the 3-glucosidic moiety of anthocyanin is important for substrate recognition by the enzyme. On the basis of the partial amino acid sequences of the purified enzyme, we isolated a cDNA encoding Ss5MaT1. Ss5MaT1 consisted of 462 amino acids and shared motifs that are commonly found among members of a versatile plant acyltransferase family, which was recently shown to include numerous homologs of unknown biochemical functions. Northern blot analysis revealed that the transcripts of Ss5MaT1 were detected in petals, sepals, bracts, and red stems, in accordance with the pigment accumulation patterns. Phylogenetic analysis suggests that the aliphatic and aromatic acylations of anthocyanins are generally catalyzed by subfamily members of the plant acyltransferase family. PMID:11598135

  7. Cyanidin-3-Glucoside-Rich Extract from Chinese Bayberry Fruit Protects Pancreatic ? Cells and Ameliorates Hyperglycemia in Streptozotocin-Induced Diabetic Mice

    PubMed Central

    Sun, Chong-De; Zhang, Bo; Zhang, Jiu-Kai; Xu, Chang-Jie; Wu, Yu-Lian; Chen, Kun-Song

    2012-01-01

    Abstract Chinese bayberry fruit is a rich source of anthocyanins, especially cyanidin-3-glucoside (C3G). The present study investigated the protective effects of C3G-rich bayberry fruit extract (CRBFE) against pancreatic ? cells against oxidative stress–induced injury as well as its hypoglycemic effect in diabetic mice. Bayberry extract from “Biqi” was used for both in vitro and in vivo testing because of its high C3G content and high antioxidant capacity. Pretreatment of ? cells with CRBFE (containing 0.5??mol/L C3G) prevented cell death, increased cellular viability, and decreased mitochondrial reactive oxygen species production and cell necrosis induced by 800 or 1,200??mol/L H2O2. CRBFE dose-dependently up-regulated pancreatic duodenal homeobox 1 gene expression, contributing to increased insulin-like growth factor II gene transcript levels and insulin protein in INS-1 cells. In addition, administration of CRBFE (150??g of C3G/10?g of body weight twice per day) significantly reduced blood glucose in streptozotocin-induced diabetic ICR mice and increased the glucose tolerance in an oral glucose tolerance test (P<.05). Such results indicated that CRBFE might be useful in prevention and control of diabetes mellitus and diabetes-associated complications. PMID:22181073

  8. TSG (2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside) from the Chinese Herb Polygonum multiflorum Increases Life Span and Stress Resistance of Caenorhabditis elegans

    PubMed Central

    Büchter, Christian; Zhao, Liang; Fritz, Gerhard; Proksch, Peter

    2015-01-01

    2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG) was isolated from Polygonum multiflorum, a plant which is traditionally used as an anti-ageing drug. We have analysed ageing-related effects of TSG in the model organism C. elegans in comparison to resveratrol. TSG exerted a high antioxidative capacity both in a cell-free assay and in the nematode. The antioxidative capacity was even higher compared to resveratrol. Presumably due to its antioxidative effects, treatment with TSG decreased the juglone-mediated induction of the antioxidative enzyme SOD-3; the induction of the GST-4 by juglone was diminished slightly. TSG increased the resistance of C. elegans against lethal thermal stress more prominently than resveratrol (50??M TSG increased mean survival by 22.2%). The level of the ageing pigment lipofuscin was decreased after incubation with the compound. TSG prolongs the mean, median, and maximum adult life span of C. elegans by 23.5%, 29.4%, and 7.2%, respectively, comparable to the effects of resveratrol. TSG-mediated extension of life span was not abolished in a DAF-16 loss-of-function mutant strain showing that this ageing-related transcription factor is not involved in the effects of TSG. Our data show that TSG possesses a potent antioxidative capacity, enhances the stress resistance, and increases the life span of the nematode C. elegans.

  9. Stimulation of callose synthesis in vivio correlates with changes in intracellular distribution of the callose synthase activator [beta]-Furfuryl-[beta]-Glucoside

    SciTech Connect

    Ohana, P.; Benziman, M.; Delmer, D.P. (Hebrew Univ., Jerusalem (Israel))

    1993-01-01

    [beta]-Furfuryl-[beta]-glucoside (FG) has been shown to be a specific endogenous activator of higher plant callose synthase. Because glycosides such as FG are usually sequestered in vacuoles, we have proposed that activation of callose synthesis in vivo may involve a change in the compartmentation on FG and Ca[sup 2+], resulting in a synergistic activation of callose synthase. The use of suspension-cultured barley (Hordeum bulbosum L.) cells provides evidence that FG is largely sequestered in the vacuole. Furthermore, conditions that lead to induction of callose synthesis in vivo correspondingly lead to elevation of the cytoplasmic concentration of FG. These conditions include the lowering of cytoplasmic pH or elevation of cytoplasmic Ca[sup 2+]. Oligogalacturonide elicitors have also been reported to cause similar changes in cytoplasmic pH and Ca[sup 2+] concentration, and such an elicitor also causes and elevation in cytoplasmic FG coupled with stimulation of callose synthesis. These results support the concept that a relative redistribution of FG between cytoplasm and vacuole may be one of the components of the signal transduction pathway for elicitation of callose synthase in vivo. 18 refs., 1 fig., 2 tabs.

  10. Intestinal SGLT1-mediated absorption and metabolism of benzyl beta-glucoside contained in Prunus mume: carrier-mediated transport increases intestinal availability.

    PubMed

    Mizuma, Takashi; Nakamura, Maya; Ina, Hiroji; Miyazaki, Toshio; Hayashi, Masahiro

    2005-03-11

    The intestinal absorption of benzyl beta-glucoside (BNZ beta glc) contained in the fruit of Prunus mume SIEB. et ZUCC. (Rosaceae), which is traditionally used as a medicinal food in Japan, was studied in rat intestines. BNZ beta glc was absorbed from the mucosal to serosal sides. Its metabolite, benzyl alcohol (BAL), was also detected on both the mucosal and serosal sides. In the presence of phloridzin (Na(+)/glucose cotransporter (SGLT1) inhibitor) or in the absence of Na+ (driving force), BNZ beta glc absorption was significantly decreased. Transport clearance of BNZ beta glc across the brush border membrane decreased as its concentration increased. These results indicate that BNZ beta glc is transported by SGLT1. Metabolic clearance of BNZ beta glc also decreased as its concentration increased. The amount ratio of BNZ beta glc to BAL on the serosal side increased with the increase of BNZ beta glc concentration. The intestinal availability of BNZ beta glc was lower in the absence of Na+ than in the presence of Na+, indicating that the SGLT1-mediated transport of BNZ beta glc increases intestinal availability by decreasing the intestinal extraction ratio. This neutraceutical study concluded that intestinal carrier-mediated transport across the brush border membrane improves the intestinal availability of nutritionally, pharmacologically or physiologically active compounds that undergo intestinal metabolism (first-pass effect). PMID:15716003

  11. Inhibition of Carrageenan-Induced Acute Inflammation in Mice by Oral Administration of Anthocyanin Mixture from Wild Mulberry and Cyanidin-3-Glucoside

    PubMed Central

    Hassimotto, Neuza Mariko Aymoto; Moreira, Vanessa; do Nascimento, Neide Galvão; Souto, Pollyana Cristina Maggio de Castro; Teixeira, Catarina; Lajolo, Franco Maria

    2013-01-01

    Anthocyanins are flavonoids which demonstrated biological activities in in vivo and in vitro models. Here in the anti-inflammatory properties of an anthocyanin-enriched fraction (AF) extracted from wild mulberry and the cyanidin-3-glucoside (C3G), the most abundant anthocyanin in diet, were studied in two acute inflammation experimental models, in the peritonitis and in the paw oedema assays, both of which were induced by carrageenan (cg) in mice. In each trial, AF and C3G (4?mg/100?g/animal) were orally administered in two distinct protocols: 30?min before and 1?h after cg stimulus. The administration of both AF and C3G suppresses the paw oedema in both administration times (P < 0.05). In the peritonitis, AF and C3G reduced the polymorphonuclear leukocytes (PMN) influx in the peritoneal exudates when administered 1?h after cg injection. AF was more efficient reducing the PMN when administered 30?min before cg. Both AF and C3G were found to suppress mRNA as well as protein levels of COX-2 upregulated by cg in both protocols, but the inhibitory effect on PGE2 production in the peritoneal exudates was observed when administered 30 min before cg (P < 0.05). Our findings suggest that AF and C3G minimize acute inflammation and they present positive contributions as dietary supplements. PMID:23484081

  12. Dimethylarginine Dimethylaminohydrolase/Nitric Oxide Synthase Pathway in Liver and Kidney: Protective Effect of Cyanidin 3-O-?-D-Glucoside on Ochratoxin-A Toxicity

    PubMed Central

    Sorrenti, Valeria; Di Giacomo, Claudia; Acquaviva, Rosaria; Bognanno, Matteo; Grilli, Ester; D’Orazio, Nicolantonio; Galvano, Fabio

    2012-01-01

    The aim of the present study was to evaluate the effect of long-term cyanidin 3-O-?-D-glucoside (C3G) and/or Ochratoxin A (OTA)-exposure on dimethylarginine dimethylamino hydrolase/nitric oxide synthase (DDAH/NOS) pathway in rats. The experiments were performed in rats supplemented with C3G (1 g/kg feed), OTA (200 ppb), and OTA + C3G. After 4 weeks of daily treatment, liver and kidneys were processed for eNOS, iNOS and DDAH-1 Western blotting, nitrite levels evaluation and DDAH activity determination. Results show that OTA is able to induce iNOS both in kidney and liver, whereas OTA is able to induce eNOS and DDAH-1 overexpression and DDAH activation only in kidney, resulting in increased nitrite levels. In kidney of OTA + C3G fed rats, iNOS, eNOS and DDAH-1 expression were less pronounced compared with those observed in the OTA-treated group. Coherent with the decreased iNOS, eNOS and DDAH-1 expression a decrease in nitrite levels and DDAH activity was observed in the OTA + C3G group. Results demonstrate that C3G is able to counteract the deleterious effects of chronic consumption of OTA and also suggest a possible involvement of iNOS-eNOS-DDAH impairment in OTA nephrocarcinogenity. PMID:22778905

  13. Transcriptional Profiling and Molecular Characterization of Astragalosides, Calycosin, and Calycosin-7-O-?-d-glucoside Biosynthesis in the Hairy Roots of Astragalus membranaceus in Response to Methyl Jasmonate.

    PubMed

    Tuan, Pham Anh; Chung, Eunsook; Thwe, Aye Aye; Li, Xiaohua; Kim, Yeon Bok; Mariadhas, Valan Arasu; Al-Dhabi, Naif Abdullah; Lee, Jai-Heon; Park, Sang Un

    2015-07-15

    We used the next-generation Illumina/Solexa HiSeq2000 platform on RNA analysis to investigate the transcriptome of Astragalus membranaceus hairy roots in response to 100 ?M methyl jasmonate (MeJA). In total, 77?758?230 clean reads were assembled into 48?636 transcripts (average length of 1398 bp), which were clustered into 23?658 loci (genes). Of these, 19?940 genes were annotated by BLASTx searches. In addition, DESeq analysis showed that 2127 genes were up-regulated, while 1247 genes were down-regulated by MeJA. Seventeen novel astragaloside (AST) biosynthetic genes and seven novel calycosin and calycosin-7-O-?-d-glucoside (CG) biosynthetic genes were isolated. The accumulation of ASTs, calycosin, and CG increased significantly in MeJA-treated hairy roots compared with control hairy roots. Our findings will provide a valuable resource for molecular characterization of AST, calycosin, and CG biosynthetic pathways and may lead to new approaches to maximize their production and biomass productivity in the hairy roots of A. membranaceus. PMID:26072674

  14. Development and validation of an HPTLC method for apigenin 7-O-glucoside in chamomile flowers and its application for fingerprint discrimination of chamomile-like materials.

    PubMed

    Guzelmeric, Etil; Vovk, Irena; Yesilada, Erdem

    2015-03-25

    Brewed tea of chamomile flowers (Matricaria recutita L.) (Asteraceae) has been extensively consumed for centuries due to either its pleasant taste or medicinal purposes. On the other hand, the major problem is difficulty in distinguishing the genuine specimen when supplying chamomile through nature-picking. Consequently flowers of other Asteraceae members resembling to chamomile in appearance may frequently be practiced by lay people or marketed in spice shops or bazaars. Evidently detection of such adulterations plays a vital role in terms of public health to avoid risk of toxicity (i.e. pyrazolidin alkaloids) and ineffective treatments (lack or insufficient concentration of the active constituents). This work presents either development and validation of a high performance thin-layer chromatographic (HPTLC) method for apigenin 7-O-glucoside which is one of the active markers in chamomile flowers or its application for the fingerprint discrimination of chamomile-like materials i.e. Anthemis spp., Bellis spp., Chrysanthemum sp. and Tanacetum sp. gathered by local people assuming as chamomile. Separation was performed on the silica gel 60 NH2 F254s HPTLC plates using the developing solvent system of ethyl acetate-formic acid-acetic acid-water (30:1.5:1.5:3, v/v/v/v). The proposed HPTLC method may also be a leading guide for the quality assessment of chamomile tea products on the market. PMID:25575175

  15. High Expression of ?-Glucosidase in Bifidobacterium bifidum BGN4 and Application in Conversion of Isoflavone Glucosides During Fermentation of Soy Milk.

    PubMed

    You, Hyun Ju; Ahn, Hyung Jin; Kim, Jin Yong; Wu, Qian Qian; Ji, Geun Eog

    2015-04-28

    In spite of the reported probiotic effects, Bifidobacterium bifidum BGN4 (BGN4) showed no ?- glucosidase activity and failed to biotransform isoflavone glucosides into the more bioactive aglycones during soy milk fermentation. To develop an isoflavone-biotransforming BGN4, we constructed the recombinant B. bifidum BGN4 strain (B919G) by cloning the structural ?- glucosidase gene from B. lactis AD011 (AD011) using the expression vector with the constitutively active promoter 919 from BGN4. As a result, B919G highly expressed ?- glucosidase and showed higher ?-glucosidase activity and heat stability than the source strain of the ?-glucosidase gene, AD011. The biotransformation of daidzin and genistin compounds using the crude enzyme extract from B919G was completed within 4 h, and the bioconversion of daidzin and genistin in soy milk during fermentation with B919G also occurred within 6 h, which was much faster and higher than with AD011. The incorporation of this ?-glucosidaseproducing Bifidobacterium strain in soy milk could lead to the production of fermented soy milk with an elevated amount of bioavailable forms of isoflavones as well as to the indigenous probiotic effects of the Bifidobacterium strain. PMID:25348696

  16. Cyanidin 3-O-Glucoside Reduces Helicobacter pylori VacA-Induced Cell Death of Gastric KATO III Cells through Inhibition of the SecA Pathway

    PubMed Central

    Kim, Sa-Hyun; Woo, Hyunjun; Park, Min; Rhee, Ki-Jong; Moon, Cheol; Lee, Dongsup; Seo, Woo Duck; Kim, Jong Bae

    2014-01-01

    Two key virulence factors of Helicobacter pylori are the secreted virulent proteins of vacuolating toxin A (VacA) and cytotoxin associated protein A (CagA) which lead to damages of gastric epithelial cells. We previously identified that the cyanidin 3-O-glucoside (C3G) inhibits the secretion of both VacA and CagA. In the current report, we show that C3G inhibits VacA secretion in a dose-dependent manner by inhibiting secretion system subunit protein A (SecA) synthesis. As SecA is involved in translocation of bacterial proteins, we predicted that inhibition of the SecA pathway by C3G should decrease H. pylori-induced cell death. To test this hypothesis, the human gastric cell line KATO III cells were co-cultured with H. pylori 60190 (VacA+/CagA+) and C3G. We found that C3G treatment caused a decrease in activation of the pro-apoptotic proteins caspase-3/-8 in H. pylori-infected cells leading to a decrease in cell death. Our data suggest that consumption of foods containing anthocyanin may be beneficial in reducing cell damage due to H. pylori infection. PMID:24904230

  17. Glucosinolate-related glucosides in Alliaria petiolata: sources of variation in the plant and different metabolism in an adapted specialist herbivore, Pieris rapae.

    PubMed

    Frisch, Tina; Agerbirk, Niels; Davis, Samantha; Cipollini, Don; Olsen, Carl Erik; Motawia, Mohammed Saddik; Bjarnholt, Nanna; Møller, Birger Lindberg

    2014-10-01

    Specialized metabolites in plants influence their interactions with other species, including herbivorous insects, which may adapt to tolerate defensive phytochemicals. The chemical arsenal of Alliaria petiolata (garlic mustard, Brassicaceae) includes the glucosinolate sinigrin and alliarinoside, a hydroxynitrile glucoside with defensive properties to glucosinolate-adapted specialists. To further our understanding of the chemical ecology of A. petiolata, which is spreading invasively in North America, we investigated the metabolite profile and here report a novel natural product, petiolatamide, which is structurally related to sinigrin. In an extensive study of North American populations of A. petiolata, we demonstrate that genetic population differences as well as developmental regulation contribute to variation in the leaf content of petiolatamide, alliarinoside, sinigrin, and a related glycoside. We furthermore demonstrate widely different metabolic fates of these metabolites after ingestion in the glucosinolate-adapted herbivore Pieris rapae, ranging from simple passage over metabolic conversion to sequestration. The differences in metabolic fate were influenced by plant ?-glucosidases, insect-mediated degradation, and the specificity of the larval gut transport system mediating sequestration. PMID:25308480

  18. Evaluation of the new anti-inflammatory compound ethyl salicylate 2-O-?-D-glucoside and its possible mechanism of action.

    PubMed

    Xin, Wenyu; Huang, Chao; Zhang, Xue; Zhang, Guidong; Ma, Xiaowei; Sun, Lan; Wang, Chao; Zhang, Dongming; Zhang, Tiantai; Du, Guanhua

    2013-02-01

    Ethyl salicylate 2-O-?-d-glucoside (ESG) is a derivative of natural salicylate isolated from Gaultheria yunnanensis (Franch.) Rehder, it has been used for the treatments of rheumatoid arthritis, swelling and pain. The aim of this study was to evaluate the anti-inflammatory effects of ESG and explore the anti-inflammatory mechanisms. We found that ESG had potent anti-inflammatory effects on the lipopolysaccharide (LPS)-activated murine macrophages RAW264.7. ESG exerted a dose-dependent inhibition of the LPS-stimulated release of the pro-inflammatory cytokines TNF-? and IL-1?. Moreover, it significantly inhibited LPS-stimulated the production of NO and PGE2 by repressing the expression of iNOS and COX protein respectively. Western blot analysis showed that ESG prominently inhibited LPS-induced activation of NF-?B in RAW264.7 cells by blocking phosphorylation of inhibitor I?B? and p65. Consistent with these results, we found that ESG prevented the nuclear translocation of NF-?B induced by LPS. Our study suggests that ESG may be effective in the treatment of inflammatory diseases by inhibiting the pro-inflammatory cytokine production and regulating the NF-?B signal pathway. PMID:23219581

  19. Cyanidin-3-glucoside derived from black soybeans ameliorate type 2 diabetes through the induction of differentiation of preadipocytes into smaller and insulin-sensitive adipocytes.

    PubMed

    Matsukawa, Toshiya; Inaguma, Tetsuya; Han, Junkyu; Villareal, Myra O; Isoda, Hiroko

    2015-08-01

    Black soybean is a health food has been reported to have antidiabetes effect. The onset of diabetes is closely associated with adipocyte differentiation, and at present, the effect of black soybean on adipocyte differentiation is unknown. Here, we investigated the antidiabetes effect of black soybean, and its anthocyanin cyanidin-3-glucoside (Cy3G), on adipocyte differentiation. Orally administered black soybean seed coat extract (BSSCE) reduced the body and white adipose tissue (WAT) weight of db/db mice accompanied by a decrease in the size of adipocytes in WAT. Furthermore, 3T3-Ll cells treated with BSSCE and Cy3G were observed to differentiate into smaller adipocytes which correlated with increased PPAR? and C/EBP? gene expressions, increased adiponectin secretion, decreased tumor necrosis factor-? secretion, activation of insulin signalling and increased glucose uptake. C2C12 myotubes cultured with conditioned medium, obtained from 3T3-L1 adipocyte cultures treated with Cy3G, also showed significantly increased expression of PGC-1?, SIRT1 and UCP-3 genes. Here we report that BSSCE, as well as its active compound Cy3G, has antidiabetes effects on db/db mice by promoting adipocyte differentiation. This notion is supported by BSSCE and Cy3G inducing the differentiation of 3T3-L1 preadipocytes into smaller, insulin-sensitive adipocytes, and it induced the activation of skeletal muscle metabolism. This is the first report on the modulation effect of Cy3G on adipocyte differentiation. PMID:25940979

  20. Protective Effect of Tetrahydroxystilbene Glucoside on 6-OHDA-Induced Apoptosis in PC12 Cells through the ROS-NO Pathway

    PubMed Central

    Tao, Lizhen; Li, Xiaofeng; Zhang, Lingling; Tian, Jiyu; Li, Xiaobing; Sun, Xin; Li, Xuefen; Jiang, Lin; Zhang, Xiaojun; Chen, Jianzong

    2011-01-01

    Oxidative stress plays an important role in the pathogenesis of neurodegenerative diseases, such as Parkinson's disease. The molecule, 2,3,5,4?-tetrahydr- oxystilbene-2-O-?-D-glucoside (TSG), is a potent antioxidant derived from the Chinese herb, Polygonum multiflorum Thunb. In this study, we investigated the protective effect of TSG against 6-hydroxydopamine-induced apoptosis in rat adrenal pheochromocytoma PC12 cells and the possible mechanisms. Our data demonstrated that TSG significantly reversed the 6-hydroxydopamine-induced decrease in cell viability, prevented 6-hydroxydopamine-induced changes in condensed nuclei and decreased the percentage of apoptotic cells in a dose-dependent manner. In addition, TSG slowed the accumulation of intracellular reactive oxygen species and nitric oxide, counteracted the overexpression of inducible nitric oxide syntheses as well as neuronal nitric oxide syntheses, and also reduced the level of protein-bound 3-nitrotyrosine. These results demonstrate that the protective effects of TSG on rat adrenal pheochromocytoma PC12 cells are mediated, at least in part, by the ROS-NO pathway. Our results indicate that TSG may be effective in providing protection against neurodegenerative diseases associated with oxidative stress. PMID:21998750

  1. Total glucosides of paeony inhibit the proliferation of fibroblast-like synoviocytes through the regulation of G proteins in rats with collagen-induced arthritis.

    PubMed

    Jia, Xiao-Yi; Chang, Yan; Sun, Xiao-Jing; Wu, Hua-Xun; Wang, Chun; Xu, Hong-Mei; Zhang, Lei; Zhang, Ling-Ling; Zheng, Yong-Qiu; Song, Li-Hua; Wei, Wei

    2014-01-01

    The aim of this study was to investigate the expression of G proteins in fibroblast-like synoviocytes (FLSs) from rats with collagen-induced arthritis (CIA) and to determine the effect of total glucosides of paeony (TGP). CIA rats were induced with chicken type II collagen (CCII) in Freund's complete adjuvant. The rats with experimental arthritis were randomly separated into five groups and then treated with TGP (25, 50, and 100mg/kg) from days 14 to 35 after immunization. The secondary inflammatory reactions were evaluated through the polyarthritis index and histopathological changes. The level of cyclic adenosine monophosphate (cAMP) was measured by radioimmunoassay. The FLS proliferation response was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The toxin-catalyzed ADP-ribosylation of G proteins was performed through autoradiography. The results show that TGP (25, 50, and 100mg/kg) significantly decreased the arthritis scores of CIA rats and improved the histopathological changes. TGP inhibited the proliferation of FLSs and increased the level of cAMP. Moreover, the FLS proliferation and the level of G?i expression were significantly increased, but the level of G?s expression was decreased after stimulation with IL-1? (10ng/ml) in vitro. TGP (12.5 and 62.5?g/ml) significantly inhibited the FLS proliferation and regulated the balance between G?i and G?s. These results demonstrate that TGP may exert its anti-inflammatory effects through the suppression of FLS proliferation, which may be associated with its ability to regulate the balance of G proteins. Thus, TGP may have potential as a therapeutic agent for the treatment of rheumatoid arthritis. PMID:24161745

  2. Pinoresinol-4,4'-di-O-beta-D-glucoside from Valeriana officinalis root stimulates calcium mobilization and chemotactic migration of mouse embryo fibroblasts.

    PubMed

    Do, Kee Hun; Choi, Young Whan; Kim, Eun Kyoung; Yun, Sung Ji; Kim, Min Sung; Lee, Sun Young; Ha, Jung Min; Kim, Jae Ho; Kim, Chi Dae; Son, Beung Gu; Kang, Jum Soon; Khan, Ikhlas A; Bae, Sun Sik

    2009-06-01

    Lignans are major constituents of plant extracts and have important pharmacological effects on mammalian cells. Here we showed that pinoresinol-4,4'-di-O-beta-D-glucoside (PDG) from Valeriana officinalis induced calcium mobilization and cell migration through the activation of lysophosphatidic acid (LPA) receptor subtypes. Stimulation of mouse embryo fibroblast (MEF) cells with 10 microM PDG resulted in strong stimulation of MEF cell migration and the EC(50) was about 2 microM. Pretreatment with pertussis toxin (PTX), an inhibitor of G(i) protein, completely blocked PDG-induced cell migration demonstrating that PDG evokes MEF cell migration through the activation of the G(i)-coupled receptor. Furthermore, pretreatment of MEF cells with Ki16425 (10 microM), which is a selective antagonist for LPA(1) and LPA(3) receptors, completely blocked PDG-induced cell migration. Likewise, PDG strongly induced calcium mobilization, which was also blocked by Ki16425 in a dose-dependent manner. Prior occupation of the LPA receptor with LPA itself completely blocked PDG-induced calcium mobilization. Finally, PDG-induced MEF cell migration was attenuated by pretreatment with a phosphatidylinositol 3-kinase (PI3K) inhibitor such as LY294002. Cells lacking downstream mediator of PI3K such as Akt1 and Akt2 (DKO cells) showed loss of PDG-induced migration. Re-expression of Akt1 (but not Akt2) completely restored PDG-induced DKO cell migration. Given these results, we conclude that PDG is a strong inducer of cell migration. We suggest that the pharmacological action of PDG may occur through the activation of an LPA receptor whereby activation of PI3K/Akt signaling pathway mediates PDG-induced MEF cell migration. PMID:19195857

  3. Comparison of anorectic and emetic potencies of deoxynivalenol (vomitoxin) to the plant metabolite deoxynivalenol-3-glucoside and synthetic deoxynivalenol derivatives EN139528 and EN139544.

    PubMed

    Wu, Wenda; Zhou, Hui-Ren; Bursian, Steven J; Pan, Xiao; Link, Jane E; Berthiller, Franz; Adam, Gerhard; Krantis, Anthony; Durst, Tony; Pestka, James J

    2014-11-01

    The mycotoxin deoxynivalenol (DON) elicits robust anorectic and emetic effects in several animal species. However, less is known about the potential for naturally occurring and synthetic congeners of this trichothecene to cause analogous responses. Here we tested the hypothesis that alterations in DON structure found in the plant metabolite deoxynivalenol-3-glucoside (D3G) and two pharmacologically active synthetic DON derivatives, EN139528 and EN139544, differentially impact their potential to evoke food refusal and emesis. In a nocturnal mouse food consumption model, oral administration with DON, D3G, EN139528, or EN139544 at doses from 2.5 to 10 mg/kg BW induced anorectic responses that lasted up to 16, 6, 6, and 3 h, respectively. Anorectic potency rank orders were EN139544>DON>EN139528>D3G from 0 to 0.5 h but DON>D3G>EN139528>EN139544 from 0 to 3 h. Oral exposure to each of the four compounds at a common dose (2.5 mg/kg BW) stimulated plasma elevations of the gut satiety peptides cholecystokinin and to a lesser extent, peptide YY3-36 that corresponded to reduced food consumption. In a mink emesis model, oral administration of increasing doses of the congeners differentially induced emesis, causing marked decreases in latency to emesis with corresponding increases in both the duration and number of emetic events. The minimum emetic doses for DON, EN139528, D3G, and EN139544 were 0.05, 0.5, 2, and 5 mg/kg BW, respectively. Taken together, the results suggest that although all three DON congeners elicited anorectic responses that mimicked DON over a narrow dose range, they were markedly less potent than the parent mycotoxin at inducing emesis. PMID:25173790

  4. Comparative study on the excretion of vitexin-4''-O-glucoside in mice after oral and intravenous administration by using HPLC.

    PubMed

    Cai, Shuang; Chen, Yinghui; Zhang, Wenjie; Ying, Xixiang

    2013-11-01

    The aim of the present study was to characterize the excretion of pure vitexin-4"-O-glucoside (VOG) in mice following oral and intravenous administration at a dose of 30 mg/kg. A sensitive and specific HPLC method with hespridin as internal standard, a Diamonsil C18 column protected with a KR C18 guard column and a mixture consisting of methanol-acetonitrile-tetrahydrofuran-0.1% glacial acetic acid (6:2:18:74, v/v/v/v) as mobile phase was developed and validated for quantitative analysis in biological samples. VOG could be excreted as prototype in excreta including urine and feces after both routes of administration, and the cumulative excretion of VOG was 24.31?±?11.10% (17.97?±?5.59% in urinary excretion; 6.34?±?5.51% in fecal excretion) following oral dosing and 5.66?±?3.94% (4.78?±?3.13% in urinary excretion; 0.88?±?0.81% in fecal excretion) following intravenous dosing. The results showed that the elimination of VOG after the two routes was fairly low, which meant that VOG was metabolized as other forms and the elimination after oral dosing was almost 4.3-fold that after intravenous dosing. For both routes of administration, VOG excreted as prototype in urine was much more than that in feces, nearly 2.83-fold for oral administration and 5.43-fold for intravenous administration, which should be attributed to enterohepatic circulation. Taken together, renal excretion was the dominant path of elimination of VOG for oral and intravenous administration in mice and biliary excretion contributed less. PMID:23760836

  5. Reversal of multidrug resistance by 5,5’-dimethoxylariciresinol-4-O-?-D-glucoside in doxorubicin-resistant human leukemia K562/DOX

    PubMed Central

    Wang, Tian-Xiao; Shi, Xiao-Yan; Cong, Yue; Wang, Shi-Guang; Wang, Ying-Ying; Zhang, Zhong-Qin

    2013-01-01

    Objective: The objective of this study was to investigate the reversal effects of 5,5’-dimethoxylariciresinol-4’-O-?-D-glucoside (DMAG) extracted from traditional Chinese medicines Mahonia on multidrug resistance (MDR) of human leukemia cells to chemotherapeutic agents. Materials and Methods: MTT(3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was performed to determine the effect of DMAG on doxorubicin sensitivity to K562/DOX cells. Propidium iodide /Hoechst 33342 double staining assay was used to investigate the effect of DMAG on doxorubicin-induced cellular apoptosis. Intracellular accumulation of doxorubicin and rhodamine 123 assay were performed to evaluate the effect of DMAG on drugs efflux activity of P-glycoprotein. Results: DMAG significantly enhanced the doxorubicin cytotoxicity to K562/DOX cells. In the presence of 1.0 ?M of DMAG, the IC50 of doxorubicin decreased from 34.93 ± 1.37 ?M to 12.51 ± 1.28 ?M. DMAG of 1.0 ?M significantly enhanced doxorubicin-induced cell apoptosis in K562/DOX cells and the enhancement was time-dependent. A significant increase in accumulation of doxorubicin in the presence of DMAG was observed. After treatment of the K562/DOX cells for 1 h with 15.0 ?M doxorubicin alone, the fluorescence intensity was 33093.12. With the addition of 1.0 ?M of DMAG, the fluorescence intensity of doxorubicin was 2.3-fold higher. A significant increase of accumulation of rhodamine 123 in the presence of DMAG was also observed. With the addition of 1.0 ?M of DMAG, the fluorescence intensity was increased by 49.11% compared with rhodamine 123 alone. Conclusion: DMAG was shown to effectively enhance chemosensitivity of resistant cells, which makes it might be a suitable candidate for potential MDR-reversing agents. PMID:24347768

  6. Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum.

    PubMed Central

    Kahn, R A; Bak, S; Svendsen, I; Halkier, B A; Møller, B L

    1997-01-01

    A cytochrome P450, designated P450ox, that catalyzes the conversion of (Z)-p-hydroxyphenylacetaldoxime (oxime) to p-hydroxymandelonitrile in the biosynthesis of the cyanogenic glucoside beta-D-glucopyranosyloxy-(S)-p-hydroxymandelonitrile (dhurrin), has been isolated from microsomes prepared from etiolated seedlings of sorghum (Sorghum bicolor L. Moench). P450ox was solubilized using nonionic detergents, and isolated by ion-exchange chromatography, Triton X-114 phase partitioning, and dye-column chromatography. P450ox has an apparent molecular mass of 55 kD, its N-terminal amino acid sequence is -ATTATPQLLGGSVP, and it contains the internal sequence MDRLVADLDRAAA. Reconstitution of P450ox with NADPH-P450 oxidoreductase in micelles of L-alpha-dilauroyl phosphatidylcholine identified P450ox as a multifunctional P450 catalyzing dehydration of (Z)-oxime to p-hydroxyphenylaceto-nitrile (nitrile) and C-hydroxylation of p-hydroxyphenylacetonitrile to nitrile. P450ox is extremely labile compared with the P450s previously isolated from sorghum. When P450ox is reconstituted in the presence of a soluble uridine diphosphate glucose glucosyltransferase, oxime is converted to dhurrin. In vitro reconstitution of the entire dhurrin biosynthetic pathway from tyrosine was accomplished by the insertion of CYP79 (tyrosine N-hydroxylase), P450ox, and NADPH-P450 oxidoreductase in lipid micelles in the presence of uridine diphosphate glucose glucosyltransferase. The catalysis of the conversion of Tyr into nitrile by two multifunctional P450s explains why all intermediates in this pathway except (Z)-oxime are channeled. PMID:9414567

  7. Cyanidin-3-O-Glucoside Ameliorates Lipopolysaccharide-Induced Injury Both In Vivo and In Vitro Suppression of NF-?B and MAPK Pathways.

    PubMed

    Ma, Ming-Ming; Li, Yan; Liu, Xiang-Yong; Zhu, Wei-Wei; Ren, Xiang; Kong, Gui-Qing; Huang, Xiao; Wang, Li-Peng; Luo, Li-Qing; Wang, Xiao-Zhi

    2015-08-01

    Cyanidin-3-O-glucoside (C3G), an anthocyanin belonging to the flavonoid family and commonly present in food and vegetables in human diet, has exhibited anti-inflammatory and anti-oxidant effects. This study aimed to investigate the protective ability of C3G against inflammatory and oxidative injuries, as well as to clarify the possible mechanism in lipopolysaccharide (LPS)-stimulated human umbilical vein endothelial cells (HUVECs) in vitro and acute respiratory distress syndrome mouse model in vivo. HUVECs or male Kunming mice were pretreated with C3G 1 h before LPS stimulation. C3G significantly inhibited the production of pro-inflammatory cytokines (tumor necrosis factor-?, interleukin (IL) -6, and IL-1?) in cell supernatants and bronchoalveolar lavage fluid (BALF) as determined by enzyme-linked immunosorbent assay. Histopathologic examination with hematoxylin and eosinstaining showed that C3G pretreatment substantially suppressed inflammatory cell infiltration, alveolar wall thickening, and interstitial edemain lung tissues. C3G markedly prevented LPS-induced elevation of malondialdehyde and myeloperoxidase levels in lung tissue homogenates, wet to dry ratio of lung tissues, total cells, and inflammatory cells (neutrophils and macrophages) in BALF. Moreover, C3G reduced superoxide dismutase activity in the lung tissue homogenates. Western blot assay also showed that C3G pretreatment significantly suppressed LPS-induced activation of nuclear factor-kappaB (NF-?B) and mitogen-activated protein kinase (MAPK) signaling pathways by blocking the phosphorylation of inhibitor ?B-?, NF-?B/P65, extracellular signal-regulated kinase, p38, and c-Jun NH2-terminal kinase in the lung tissues. In summary, C3G may ameliorate LPS-induced injury, which results from inflammation and oxidation, by inhibiting NF-?B and MAPK pathways and playing important anti-inflammatory and anti-oxidative roles. PMID:25752620

  8. Cucurbitacin L 2-O-?-Glucoside Demonstrates Apoptogenesis in Colon Adenocarcinoma Cells (HT-29): Involvement of Reactive Oxygen and Nitrogen Species Regulation

    PubMed Central

    Abdelwahab, Siddig Ibrahim; Hassan, Loiy Elsir Ahmed; Abdul Majid, Amin M. S.; Yagi, Sakina M. Ahmed; Mohan, Syam; Elhassan Taha, Manal Mohamed; Ahmad, Syahida; Chuen, Cheah Shiau; Narrima, Putri; Rais, Mohd Mustafa; Syam, Suvitha; Moharam, Bushra Abdulkarim; Hadi, A. Hamid A.

    2012-01-01

    Emerging evidence suggests that reactive oxygen (ROS) and nitrogen (RNS) species can contribute to diverse signalling pathways of inflammatory and tumour cells. Cucurbitacins are a group of highly oxygenated triterpenes. Many plants used in folk medicine to treat cancer have been found to contain cucurbitacins displaying potentially important anti-inflammatory actions. The current study was designed to investigate the anti-ROS and -RNS effects of cucurbitacin L 2-O-?-glucoside (CLG) and the role of these signaling factors in the apoptogenic effects of CLG on human colon cancer cells (HT-29). This natural cucurbitacin was isolated purely from Citrullus lanatus var. citroides (Cucurbitaceae). The results revealed that CLG was cytotoxic to HT-29. CLG increased significantly (P < 0.05) RNA and protein levels of caspase-3 in HT-29 cells when verified using a colorimetric assay and realtime qPCR, respectively. The results showed that lipopolysaccharide/interferon-gamma (LPS/INF-?) increased nitrous oxide (NO) production inR AW264.7macrophages, whereas N(G)-nitro-L-argininemethyl ester (L-NAME) and CLG curtailed it. This compound did not reveal any cytotoxicity on RAW264.7 macrophages and human normal liver cells (WRL-68) when tested using the MTT assay. Findings of ferric reducing antioxidant power (FRAP) and oxygen radical absorption capacity (ORAC) assays demonstrate the antioxidant properties of CLG. The apoptogenic property of CLG on HT-29 cells is thus related to inhibition of reactive nitrogen and oxygen reactive species and the triggering of caspase-3-regulated apoptosis. PMID:22685485

  9. Cyanidin-3-O-beta-glucoside inhibits iNOS and COX-2 expression by inducing liver X receptor alpha activation in THP-1 macrophages.

    PubMed

    Wang, Qing; Xia, Min; Liu, Chi; Guo, Honghui; Ye, Qingyuan; Hu, Yan; Zhang, Yinghui; Hou, Mengjun; Zhu, Huilian; Ma, Jing; Ling, Wenhua

    2008-08-01

    Anthocyanins belong to a large and widespread group of water-soluble phytochemicals and exhibit potent antioxidative and anti-inflammatory properties; however, the molecular mechanisms of these biochemical actions mediated by anthocyanins remain unclear. In this study, our data show that pretreatment of THP-1 macrophages with Cyanidin-3-O-beta-glucoside (C3G) for 12 h can enhance the expression and transcriptional activities of the nuclear receptor peroxisome proliferator-activated receptor gamma (PPARgamma) and liver X receptor alpha (LXRalpha). Furthermore, pretreatment of these cells with C3G for 12 h causes dose-dependent inhibition of lipopolysaccharide (LPS)-induced nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at both the mRNA and protein levels together with a decrease in nitric oxide (NO) and prostaglandin E(2) (PGE(2)) production. Consequently, addition of geranylgeranyl pyrophosphate ammonium salt (GGPP), an LXRalpha antagonist, significantly downregulates the inhibitory effect of C3G on LPS-induced iNOS and COX-2 expression in THP-1 macrophages, whereas the PPARgamma antagonist GW9662 has no effect. Further investigation revealed that LXRalpha might interfere with LPS-induced iNOS and COX-2 expression by suppressing the functional activation of nuclear factor-kappaB (NF-kappaB), not - as was previously proposed - by reducing NF-kappaB nuclear translocation. Taken together, these results indicate that LXRalpha activation has an essential role in the anti-inflammatory property of C3G. Moreover, they provide new insight into the molecular basis for the anti-inflammatory property of anthocyanins. PMID:18619979

  10. Rapid separation of cyanidin-3-glucoside and cyanidin-3-rutinoside from crude mulberry extract using high-performance countercurrent chromatography and establishment of a volumetric scale-up process.

    PubMed

    Choi, Soo-Jung; Choi, Janggyoo; Lee, Chang Uk; Yoon, Shin Hee; Bae, Soo Kyung; Chin, Young-Won; Kim, Jinwoong; Yoon, Kee Dong

    2015-06-01

    This study describes the rapid separation of mulberry anthocyanins; namely, cyanidin-3-glucoside and cyanidin-3-rutinoside, using high-performance countercurrent chromatography, and the establishment of a volumetric scale-up process from semi-preparative to preparative-scale. To optimize the separation parameters, biphasic solvent systems composed of tert-butyl methyl ether/n-butanol/acetonitrile/0.01% trifluoroacetic acid, flow rate, sample amount and rotational speed were evaluated for the semi-preparative-scale high-performance countercurrent chromatography. The optimized semi-preparative-scale high-performance countercurrent chromatography parameters (tert-butyl methyl ether/n-butanol/acetonitrile/0.01% trifluoroacetic acid, 1:3:1:5, v/v; flow rate, 4.0 mL/min; sample amount, 200-1000 mg; rotational speed, 1600 rpm) were transferred directly to a preparative-scale (tert-butyl methyl ether/n-butanol/acetonitrile/0.01% trifluoroacetic acid, 1:3:1:5, v/v; flow rate, 28 mL/min; sample amount, 5.0-10.0 g; rotational speed, 1400 rpm) to achieve separation results identical to cyanidin-3-glucoside and cyanidin-3-rutinoside. The separation of mulberry anthocyanins using semi-preparative high-performance countercurrent chromatography and its volumetric scale-up to preparative-scale was addressed for the first time in this report. PMID:25800228

  11. Separation of flavanone enantiomers and flavanone glucoside diastereomers from Balanophora involucrata Hook. f. by capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18 column.

    PubMed

    Pan, Jianyu; Zhang, Si; Yan, Liushui; Tai, Jiandong; Xiao, Qiang; Zou, Kun; Zhou, Yuan; Wu, Jun

    2008-03-21

    A pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-5-O-beta-d-glucopyranoside (1a, 1b), was successfully separated by RP-C(18) high-performance liquid chromatography from Balanophora involucrata Hook. f. Some other compounds, including a pair of flavanone enantiomers, (2R)- and (2S)-eriodictyol (2a, 2b), and a pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-7-O-beta-d-glucopyranoside(3a, 3b), were separated by capillary electrophoresis from the same plant. The absolute configurations at C-2 of 1a and 1b were determined based on their circular dichroism spectra. Enzymatic hydrolysis of 1a and 1b by beta-d-glucosidase afforded (2R)- and (2S)-eriodictyol, respectively, which were used as the authentic standards for co-elution to determine the migration order of the enantiomers, 2a and 2b. We also report the first example of identifying the migration order of 2a and 2b and resolving the separation of 3a and 3b by capillary electrophoresis. In addition, 1a was unambiguously characterized for the first time by NMR spectra. PMID:18291407

  12. Identification, properties, and genetic control of UDP-glucose: cyanidin-3-rhamnosyl-(1 leads to 6)-glucoside-5-O-glucosyltransferase isolated from petals of the red campion (Silene dioica).

    PubMed

    Kamsteeg, J; van Brederode, J; van Nigtevecht, G

    1978-12-01

    An enzyme catalyzing the transfer of the glucosyl moiety of UDP-glucose to the 5-hydroxyl group of cyanidin-3-rhamnosyl-(1 leads to 6)-glucoside has been demonstrated in petal extracts of Silene dioica plants. This glucosyltransferase activity was not detectable in green parts of these plants. The enzyme activity is controlled by a single dominant gene M; no glucosyltransferase activity could be demonstrated in petals of m/m plants. The enzyme was purified eightyfold by PVP and Sephadex G50 chromatography. The glucosyltransferase had a pH optimum of 7.4, had a molecular weight of about 55,000, was stimulated by divalent metal ions, and had a "true Km" values of 0.5 x 10(-3) M for UDP-glucose and 3.6 x 10(-3) M for cyanidin-3-rhamnosylglucoside. Pelargonidin-3-rhamnosylglucoside also could serve as acceptor. The enzyme did not catalyze the glucosylation of the 5-hydroxyl group of cyanidin-3-glucoside, although in petals of M/- n/n mutants cyanidin-3,5-diglucoside is present. ADP-glucose could not serve as a glucosyl donor. PMID:751641

  13. Novel oxidation products of cyanidin 3-O-glucoside with 2,2'-azobis-(2,4-dimethyl)valeronitrile and evaluation of anthocyanin content and its oxidation in black rice.

    PubMed

    Kamiya, Haruna; Yanase, Emiko; Nakatsuka, Shin-Ichi

    2014-07-15

    The radical oxidation mechanism of anthocyanin derivatives was investigated by the reaction of cyanidin 3-O-glucoside in the presence of radical initiator 2,2'-azobis-(2,4-dimethyl)valeronitrile (AMVN) in EtOH and aqueous CH3CN. Six different oxidation products were isolated, depending on the solvent employed. These products were identified using NMR spectroscopy and multistep derivatisation reactions. Of the products obtained, two novel oxidised anthocyanin derivatives were isolated from black rice under prolonged storage. A radical reaction mechanism is proposed on the basis of these reaction products. Quantification of oxidised anthocyanins in black rice is demonstrated as a method to verify freshness of the rice. PMID:24594178

  14. Quercetin-3-glucoside increases low-density lipoprotein receptor (LDLR) expression, attenuates proprotein convertase subtilisin/kexin 9 (PCSK9) secretion, and stimulates LDL uptake by Huh7 human hepatocytes in culture

    PubMed Central

    Mbikay, Majambu; Sirois, Francine; Simoes, Sonia; Mayne, Janice; Chrétien, Michel

    2014-01-01

    Low-density lipoprotein receptor (LDLR) mediates hepatic clearance of plasma cholesterol; proprotein convertase subtilisin/kexin 9 (PCSK9) opposes this clearance by promoting LDLR degradation. The plant flavonoid quercetin-3-?-d-glucoside (Q3G) has been shown to reduce hypercholesterolemia in experimental animals. Here, we examined how it affects LDLR and PCSK9 expression as well as LDL uptake by human Huh7 hepatocytes. At low micromolar concentrations, Q3G increased LDLR expression, reduced PCSK9 secretion, and stimulated LDL uptake. It also diminished intracellular sortilin, a sorting receptor known to facilitate PCSK9 secretion. Thus, as an LDLR inducer and a PCSK9 anti-secretagogue, Q3G may represent an effective anti-cholesterolemic agent. PMID:25349780

  15. Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin

    Microsoft Academic Search

    Søren Bak; Rachel Alice Kahn; Hanne Linde Nielsen; Birger Lindberg Møller; Barbara Ann Halkier

    1998-01-01

    A cDNA encoding the multifunctional cytochrome P450, CYP71E1, involved in the biosynthesis of the cyanogenic glucoside dhurrin from Sorghum bicolor (L.) Moench was isolated. A PCR approach based on three consensus sequences of A-type cytochromes P450 – (V\\/I)KEX(L\\/F)R, FXPERF, and PFGXGRRXCXG – was applied. Three novel cytochromes P450 (CYP71E1, CYP98, and CYP99) in addition to a PCR fragment encoding sorghum

  16. The biosynthesis of cyanogenic glucosides in higher plants. The (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime as intermediates in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench

    SciTech Connect

    Halkier, B.A.; Olsen, C.E.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Frederiksberg C (Denmark))

    1989-11-25

    The biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin has been studied with a microsomal preparation obtained from etiolated seedlings of sorghum. The biosynthetic pathway involves tyrosine, N-hydroxytyrosine, and p-hydroxyphenylacetaldehyde oxime as early intermediates. The use of deuterium-labeled tyrosine and mass spectrometric analyses demonstrate that the alpha-hydrogen atom of tyrosine is retained in the conversion of tyrosine to p-hydroxyphenylacetaldehyde oxime. This excludes p-hydroxyphenylpyruvic acid oxime as intermediate in the pathway. A high pressure liquid chromatography method was developed to separate the (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime. The microsomal enzyme system was found to produce initially the (E)-isomer of p-hydroxyphenylacetaldehyde oxime. An isomerase then converts the (E)-isomer to the (Z)-isomer, which is the isomer preferentially utilized by the microsomal enzyme system in the subsequent biosynthetic reactions. The (E)-isomer produced in situ is more efficiently converted to the (Z)-isomer than exogenously added (E)-isomer and may thus be metabolically channeled.

  17. Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.

    PubMed

    Ibrahim, N A; Shalaby, A S; Farag, R S; Elbaroty, G S; Nofal, S M; Hassan, E M

    2008-04-15

    Flavonoid glycosides, orientin and apigenin 3, 8-di-C-glycosides in addition to, iridoid compound, aucubin were isolated from the ethanolic extract of Vitex agnus-castus fruits. Their structures were identified on the basis of the spectroscopic data. The estrogenic activity of the ethanolic extract in two dose levels 0.6 and 1.2 g kg(-1) per body weight (b.w.) was studied by the vaginal smear, and uterine weight methods for normal and ovariectomized female rats. The extract induced significant increase in the uterine weight of ovariectomized rats at two dose levels comparable to that of control group. The percentages of the total average number of scores were increased significantly too. Significant increases in plasma progesterone and total estrogens levels were shown at the two dose levels when compared to that of control group. On the other side, the extract induced significant reduction in luteinizing and plasma prolactin hormones. PMID:18415863

  18. Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.).

    PubMed

    Masuzaki, S; Shigyo, M; Yamauchi, N

    2006-02-01

    The extrachromosome 5A of shallot (Allium cepa L., genomes AA) has an important role in flavonoid biosynthesis in the scaly leaf of Allium fistulosum-shallot monosomic addition lines (FF+nA). This study deals with the production and biochemical characterisation of A. fistulosum-shallot multiple alien addition lines carrying at least 5A to determine the chromosomal locations of genes for quercetin formation. The multiple alien additions were selected from the crossing between allotriploid FFA (female symbol) and A. fistulosum (male symbol). The 113 plants obtained from this cross were analysed by a chromosome 5A-specific PGI isozyme marker of shallot. Thirty plants were preliminarily selected for an alien addition carrying 5A. The chromosome numbers of the 30 plants varied from 18 to 23. The other extrachromosomes in 19 plants were completely identified by using seven other chromosome markers of shallot. High-performance liquid chromatography analyses of the 19 multiple additions were conducted to identify the flavonoid compounds produced in the scaly leaves. Direct comparisons between the chromosomal constitution and the flavonoid contents of the multiple alien additions revealed that a flavonoid 3'-hydroxylase (F3'H) gene for the synthesis of quercetin from kaempferol was located on 7A and that an anonymous gene involved in the glucosidation of quercetin was on 3A or 4A. As a result of supplemental SCAR analyses by using genomic DNAs from two complete sets of A. fistulosum-shallot monosomic additions, we have assigned F3'H to 7A and flavonol synthase to 4A. PMID:16411131

  19. 2-nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.

    PubMed Central

    Halkier, B A; Lykkesfeldt, J; Møller, B L

    1991-01-01

    The biosynthetic pathway for the cyanogenic glucoside dhurrin derived from tyrosine has been studied in vitro by using [18O]oxygen and a microsomal enzyme system obtained from etiolated sorghum seedlings. The products formed were purified by HPLC and TLC, and the incorporation of [18O]oxygen was monitored by mass spectrometry. In the presence of NADPH and [18O]dioxygen, L-tyrosine is converted to (E)- and (Z)-p-hydroxyphenylacetaldehyde oxime with quantitative incorporation of an [18O]oxygen atom into the oxime function. The first step in this conversion is the N-hydroxylation of L-tyrosine to N-hydroxytyrosine. Administration of N-hydroxytyrosine as a substrate results in the production of 1-nitro-2-(p-hydroxyphenyl)ethane in addition to (E)- and (Z)-p-hydroxyphenylacetaldehyde oxime, with quantitative incorporation of a single [18O]oxygen atom in all three products. These data demonstrate that the conversion of N-hydroxytyrosine to p-hydroxyphenylacetaldehyde oxime involves additional N-hydroxylation and N-oxidation reactions giving rise to the formation of 2-nitro-3-(p-hydroxyphenyl)propionate, which by decarboxylation produces aci-1-nitro-2-(p-hydroxyphenyl)ethane. Both compounds are additional intermediates in the pathway. The two [18O]oxygen atoms introduced by the N-hydroxylations are enzymatically distinguishable as demonstrated by the specific loss of the oxygen atom introduced by the first N-hydroxylation reaction in the subsequent conversion of aci-1-nitro-2-(p-hydroxyphenyl)ethane to (E)-p-hydroxyphenylacetaldehyde oxime. A high flux of intermediates through the microsomal enzyme system is obtained with N-hydroxytyrosine as a substrate. This renders the conversion of the aci-nitro compound rate limiting and results in its release from the active site of the enzyme system and accumulation of the tautomeric nitro compound. PMID:11607147

  20. Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (Prepared by reverse-phase evaporation) by Triton X-100 octyl glucoside, and sodium cholate

    SciTech Connect

    Paternostre, M.T.; Roux, M.; Rigaud, J.L.

    1988-04-19

    The mechanisms governing the solubilization by Triton X-100, octyl glucoside, and sodium cholate of large unilamellar liposomes prepared by reverse-phase evaporation were investigated. The solubilization process is described by the three-stage model previously proposed for the detergents. In stage I, detergent monomers are incorporated into the phospholipid bilayers until they saturate the liposomes. At this point, i.e., stage II, mixed phospholipid-detergent micelles begin to form. By stage III, the lamellar to micellar transition is complete and all the phospholipids are present as mixed micelles. The turbidity of liposome preparations was systematically measured as a function of the amount of detergent added for a wide range of phospholipid concentrations. The results allowed a quantitative determination of the effective detergent to lipid molar ratios in the saturated liposomes. The monomer concentrations of the three detergents in the aqueous phase were also determined at the lamellar to micellar transitions. These transitions were also investigated by /sup 31/P NMR spectroscopy, and complete agreement was found with turbidity measurements. Freeze-fracture electron microscopy and permeability studies in the sublytic range of detergent concentrations indicated that during stage I of solubilization detergent partitioning between the aqueous phase and the lipid bilayer greatly affects the basic permeability of the liposomes without significantly changing the morphology of the preparations. A rough approximation of the partition coefficients was derived from the turbidity and permeability data. It is concluded that when performed systematically, turbidity measurements constitute a very convenient and powerful technique for the quantitative study of the liposome solubilization process by detergents.

  1. 2-Nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L. ) Moench

    SciTech Connect

    Halkier, B.A.; Lykkesfeldt, J.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Copenhagen (Denmark))

    1991-01-15

    The biosynthetic pathway for the cyanogenic glucoside dhurrin derived from tyrosine has been studied in vitro by using ({sup 18}O)oxygen and a microsomal enzyme system obtained from etiolated sorghum seedlings. The products formed were purified by HPLC and TLC, and the incorporation of ({sup 18}O)oxygen was monitored by mass spectrometry. In the presence of NADPH and ({sup 18}O)dioxygen, L-tyrosine is converted to (E)- and (Z)-p-hydroxyphenylacetaldhyde oxime with quantitative incorporation of an ({sup 18}O)oxygen atom into the oxime function. These data demonstrate that the conversion of N-hydroxytyrosine to p-hydroxyphenylacetaldehyde oxime involves additional N-hydroxylation and N-oxidation reactions giving rise to the formation of 2-nitro-3-(p-hydroxyphenyl)propionate, which by decarboxylation produces aci-1-nitro-2-(p-hydroxyphenyl)ethane. Both compounds are additional intermediates in the pathway. The two ({sup 18}O)oxygen atoms introduced by the N-hydroxylations are enzymatically distinguishable as demonstrated by the specific loss of the oxygen atom introduced by the first N-hydroxylation reaction in the subsequent conversion of aci-1-nitro-2-(p-hydroxyphenyl)ethane to (E)-p-hydroxyphenylacetaldehyde oxime. A high flux of intermediates through the microsomal enzyme system is obtained with N-hydroxytyrosine as a substrate. This renders the conversion of the aci-nitro compound rate limiting and results in its release from the active site of the enzyme system and accumulation of the tautomeric nitro compound.

  2. The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate

    SciTech Connect

    Halkier, B.A.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Copenhagen (Denmark))

    1990-12-05

    N-Hydroxytyrosine, (E)- and (Z)-p-hydroxyphenyl-acetaldehyde oxime, p-hydroxyphenylacetonitrile, and p-hydroxymandelonitrile are established intermediates in the biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin. Simultaneous measurements of oxygen consumption and biosynthetic activity using a microsomal enzyme system isolated from etiolated sorghum seedlings demonstrate a requirement for three oxygen molecules in the conversion of tyrosine to p-hydroxymandelonitrile. Two oxygen molecules are consumed in the conversion of tyrosine to (E)-p-hydroxyphenylacetaldehyde oxime, indicating the existence of a previously undetected hydroxylation step in addition to that resulting in the formation of N-hydroxytyrosine. Radioactively labeled 1-nitro-2-(p-hydroxyphenyl)ethane was chemically synthesized and tested as a possible intermediate. Biosynthetic experiments demonstrate that the microsomal enzyme system metabolizes the nitro compound to the subsequent intermediates in dhurrin synthesis (Km = 0.05 mM; Vmax = 14 nmol/mg of protein/h). Low amounts of 1-nitro-2-(p-hydroxyphenyl)ethane are produced in the microsomal reaction mixtures when tyrosine is used as substrate. These data support the involvement of 1-nitro-2-(p-hydroxyphenyl)ethane or more likely its aci-nitro tautomer as an intermediate between N-hydroxytyrosine and p-hydroxyphenylacetaldehyde oxime. The conversion of (E)-p-hydroxyphenylacetaldehydeoxime to p-hydroxymandelonitrile requires a single oxygen molecule. The oxygen molecule is utilized for hydroxylation of p-hydroxyphenylacetonitrile into p-hydroxymandelonitrile. This indicates that the conversion of p-hydroxyphenylacetaldehyde oxime into p-hydroxyphenylacetonitrile proceeds by a simple dehydration reaction.

  3. Isolation of the heme-thiolate enzyme cytochrome P-450TYR, which catalyzes the committed step in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.

    PubMed Central

    Sibbesen, O; Koch, B; Halkier, B A; Møller, B L

    1994-01-01

    The cytochrome P-450 enzyme (hemethiolate enzyme) that catalyzes the N-hydroxylation of L-tyrosine to N-hydroxytyrosine, the committed step in the biosynthesis of the cyanogenic glucoside dhurrin, has been isolated from microsomes prepared from etiolated seedlings of Sorghum bicolor (L.) Moench. The cytochrome P-450 enzyme was solubilized with the detergents Renex 690, reduced Triton X-100, and 3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate and isolated by ion-exchange (DEAE-Sepharose) and dye (Cibacron blue and reactive red 120) column chromatography. To prevent irreversible aggregation of the cytochrome P-450 enzyme, the isolation procedure was designed without any concentration step--i.e., with dilution of the ion-exchange gel with gel filtration material. The isolated enzyme, which we designate the cytochrome P-450TYR enzyme, gives rise to the specific formation of a type I substrate binding spectrum in the presence of L-tyrosine. The microsomal preparation contains 0.2 nmol of total cytochrome P-450/mg of protein. The cytochrome P-450TYR enzyme is estimated to constitute approximately 20% of the total cytochrome P-450 content of the microsomal membranes and about 0.2% of their total protein content. The apparent molecular mass of the cytochrome P-450TYR enzyme is 57 kDa, and the N-terminal amino acid sequence is ATMEVEAAAATVLAAP. A polyclonal antibody raised against the isolated cytochrome P-450TYR enzyme is specific as monitored by Western blot analysis and inhibits the in vitro conversion of L-tyrosine to p-hydroxymandelonitrile catalyzed by the microsomal system. The cytochrome P-450TYR enzyme exhibits high substrate specificity and acts as an N-hydroxylase on a single endogenous substrate. The reported isolation procedure based on dye columns constitutes a gentle isolation method for cytochrome P-450 enzymes and is of general use as indicated by its ability to separate cytochrome P-450TYR from the cytochrome P-450 enzyme catalyzing the C-hydroxylation of p-hydroxyphenylacetonitrile and from cinnamic acid 4-hydroxylase. Images PMID:7937883

  4. Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.

    PubMed

    Gonda, S; Tóth, L; Parizsa, P; Nyitrai, M; Vasas, G

    2010-01-01

    Five species of Plantago genus, namely P. lanceolata, P. major, P. media, P. altissima and P. maritima were screened for iridoid content (CE-MEKC), total caffeoyl phenylethanoid glycoside (CPG) content and antioxidant activity (CUPRAC assay). The five species could be distinguished by TLC pattern analysis in a single run in a system commonly used for quality management of P. lanceolata leaves, as shown by cluster analysis of major bands; with the exception, that P. altissima and P. lanceolata did not show enough pattern difference to be fully separated. P. maritima was shown to have the highest antioxidant capacity (0.42 ?mol ascorbic acid equivalent (AAE)/g DW), and the highest level of CPGs (4.29%). P. altissima was shown to be chemically indistinguishable from P. lanceolata with repsect to iridoid content (aucubin 0.55 ± 0.04%, 0.68 ± 0.23%, catalpol 0.66 ± 0.13% and 0.89 ± 0.22%, respectively), CPG content (2.40 ± 0.38% and 2.54 ± 0.56%, respectively) and antioxidant capacity (0.2206 ± 0.0290 and 0.2428 ± 0.0191 ?mol AAEAC/g DW). The presented data show the potency of medicinal use of Hungarian wild populations of the studied five species, especially in the case of P. maritima, and that P. altissima can be a potential replacement of P. lanceolata in herbal mixtures. PMID:21565762

  5. Characterization of multiple absorbed constituents in rats after oral administration of Paederia scandens decoction.

    PubMed

    Jiang, Weixin; Jin, Di; Li, Zhixiong; Sun, Zhaolin; Chen, Mingcang; Wu, Bin; Huang, Chenggang

    2012-07-01

    Paederia scandens (Lour.) Merri. (Jishiteng in Chinese) is a Chinese traditional medicine widely used in treating various diseases. However, its active components have remained unknown. In the present study, a rapid and sensitive method by high-performance liquid chromatography coupled with electrospray ionization mass spectrometry (HPLC-MSn) techniques was employed to investigate the absorbed constituents in rats after oral administration of Paederia scandens decoction. By comparing their MS data with those of authentic compounds and published data, a total of six compounds (paederosid, 1; paederosidic acid, 2; paederosidic acid methyl ester, 3; 6-hydroxy geniposide, 4; asperuloside, 5; and deacetyl asperuloside, 6) were identified in the P. scandens decoction samples. In addition, a total of seven compounds, including three iridoid glucosides and four of their metabolites, were identified in rat urine samples after administration. In addition, six compounds, including four iridoid glucosides and two of their metabolites, were identified in rat serum samples after administration. Our results significantly narrow the range of potentially active compounds in P. scandens decoction, and build a solid foundation for future research on its mechanism. PMID:22860258

  6. Sonication-assisted Agrobacterium rhizogenes-mediated transformation of Verbascum xanthophoeniceum Griseb. for bioactive metabolite accumulation.

    PubMed

    Georgiev, Milen I; Ludwig-Müller, Jutta; Alipieva, Kalina; Lippert, Annemarie

    2011-05-01

    An efficient protocol for the establishment of transformed root culture of Verbascum xanthophoeniceum using sonication-assisted Agrobacterium rhizogenes-mediated transformation is reported. Only 10 days after the inoculation with A. rhizogenes ATCC 15834 and 45 s ultrasound exposure, hairy roots appeared on 75% of the Verbascum leaves. Ten hairy root lines were isolated, although only half of them were free of bacterial contamination and started growing when excised from mother explants. The transgenic nature of the most vigorously growing hairy root clones (VX1 and VX6) was confirmed by polymerase chain reaction. Under submerged cultivation both hairy root clones accumulated high biomass amounts (12.8 and 14.3 g L(-1), respectively) and significant amounts of bioactive phenylethanoid glycoside verbascoside (over 6-times more than in mother plant leaves). LC-APCI-MS analyses confirmed verbascoside accumulation in hairy root clones along with three other phenylethanoid glycosides (forsythoside B, leucosceptoside B and martynoside) and an iridoid glycoside aucubin. This is the first report on the induction of hairy roots of Verbascum plants. PMID:21184229

  7. Host Shifts from Lamiales to Brassicaceae in the Sawfly Genus Athalia

    PubMed Central

    Opitz, Sebastian E. W.; Boevé, Jean-Luc; Nagy, Zoltán Tamás; Sonet, Gontran; Koch, Frank; Müller, Caroline

    2012-01-01

    Plant chemistry can be a key driver of host shifts in herbivores. Several species in the sawfly genus Athalia are important economic pests on Brassicaceae, whereas other Athalia species are specialized on Lamiales. These host plants have glucosides in common, which are sequestered by larvae. To disentangle the possible direction of host shifts in this genus, we examined the sequestration specificity and feeding deterrence of iridoid glucosides (IGs) and glucosinolates (GSs) in larvae of five species which either naturally sequester IGs from their hosts within the Plantaginaceae (Lamiales) or GSs from Brassicaceae, respectively. Furthermore, adults were tested for feeding stimulation by a neo-clerodane diterpenoid which occurs in Lamiales. Larvae of the Plantaginaceae-feeders did not sequester artificially administered p-hydroxybenzylGS and were more deterred by GSs than Brassicaceae-feeders were by IGs. In contrast, larvae of Brassicaceae-feeders were able to sequester artificially administered catalpol (IG), which points to an ancestral association with Lamiales. In line with this finding, adults of all tested species were stimulated by the neo-clerodane diterpenoid. Finally, in a phylogenetic tree inferred from genetic marker sequences of 21 Athalia species, the sister species of all remaining 20 Athalia species also turned out to be a Lamiales-feeder. Fundamental physiological pre-adaptations, such as the establishment of a glucoside transporter, and mechanisms to circumvent activation of glucosides by glucosidases are therefore necessary prerequisites for successful host shifts between Lamiales and Brassicaceae. PMID:22485146

  8. Host shifts from Lamiales to Brassicaceae in the sawfly genus Athalia.

    PubMed

    Opitz, Sebastian E W; Boevé, Jean-Luc; Nagy, Zoltán Tamás; Sonet, Gontran; Koch, Frank; Müller, Caroline

    2012-01-01

    Plant chemistry can be a key driver of host shifts in herbivores. Several species in the sawfly genus Athalia are important economic pests on Brassicaceae, whereas other Athalia species are specialized on Lamiales. These host plants have glucosides in common, which are sequestered by larvae. To disentangle the possible direction of host shifts in this genus, we examined the sequestration specificity and feeding deterrence of iridoid glucosides (IGs) and glucosinolates (GSs) in larvae of five species which either naturally sequester IGs from their hosts within the Plantaginaceae (Lamiales) or GSs from Brassicaceae, respectively. Furthermore, adults were tested for feeding stimulation by a neo-clerodane diterpenoid which occurs in Lamiales. Larvae of the Plantaginaceae-feeders did not sequester artificially administered p-hydroxybenzylGS and were more deterred by GSs than Brassicaceae-feeders were by IGs. In contrast, larvae of Brassicaceae-feeders were able to sequester artificially administered catalpol (IG), which points to an ancestral association with Lamiales. In line with this finding, adults of all tested species were stimulated by the neo-clerodane diterpenoid. Finally, in a phylogenetic tree inferred from genetic marker sequences of 21 Athalia species, the sister species of all remaining 20 Athalia species also turned out to be a Lamiales-feeder. Fundamental physiological pre-adaptations, such as the establishment of a glucoside transporter, and mechanisms to circumvent activation of glucosides by glucosidases are therefore necessary prerequisites for successful host shifts between Lamiales and Brassicaceae. PMID:22485146

  9. Bioactive iridoids and a new lignan from Allamanda cathartica and Himatanthus fallax from the Suriname rainforest.

    PubMed

    Abdel-Kader, M S; Wisse, J; Evans, R; van der Werff, H; Kingston, D G

    1997-12-01

    Bioassay-guided fractionation of the EtOAc extract of both Allamanda cathartica and Himatanthus fallax (Apocynaceae) using the Sc-7 yeast strain resulted in the isolation of the weakly cytotoxic isoplumericin and plumericin. In addition, the new lignan 7(R)-methoxy-8-epi-matairesional and three known compounds, plumieride, matairesinol, and pinoresinol, were isolated from H. fallax. PMID:9428163

  10. Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor

    Microsoft Academic Search

    Hamdi K.. Hamdi; Raquel Castellon

    2005-01-01

    Oleuropein, a non-toxic secoiridoid derived from the olive tree, is a powerful antioxidant and anti-angiogenic agent. Here, we show it to be a potent anti-cancer compound, directly disrupting actin filaments in cells and in a cell-free assay. Oleuropein inhibited the proliferation and migration of advanced-grade tumor cell lines in a dose-responsive manner. In a novel tube-disruption assay, Oleuropein irreversibly rounded

  11. Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya

    Microsoft Academic Search

    David S. Seigler; Guido F. Pauli; Adolf Nahrstedt; Rosemary Leen

    2002-01-01

    Leaf and stem material of Passiflora edulis (Passifloraceae) contains the new cyanogenic glycosides (2R)–?-d-allopyranosyloxy-2-phenylacetonitrile (1a) and (2S)–?-d-allopyranosyloxy-2-phenylacetonitrile (1b), along with smaller amounts of (2R)–prunasin (2a), sambunigrin (2b), and the alloside of benzyl alcohol (4); the major cyanogens of the fruits are (2R)–prunasin (2a) and (2S)–sambunigrin (2b). The major cyanogenic glycoside of Carica papaya (Caricaceae) is 2a; only small amounts of

  12. Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides

    Microsoft Academic Search

    Hye-Yeon Park; Mihyang Kim; Jaehong Han

    A Gram-negative anaerobic microorganism, MRG-1, isolated from human intestine showed high activities of deglycosylation and\\u000a reduction of daidzin, based on rapid TLC analysis. A rod-shaped strain MRG-1was identified as a new species showing 91.0%\\u000a homology to Coprobacillus species, based on 16S rRNA sequence analysis. The strain MRG-1 showed ?-glucosidase activity toward daidzin and genistin,\\u000a and daidzein and genistein were produced,

  13. Biosynthesis of benzylglucosinolate, cyanogenic glucosides and phenylpropanoids in Carica papaya

    Microsoft Academic Search

    Richard N. Bennett; Guy Kiddle; Roger M. Wallsgrove

    1997-01-01

    Benzylglucosinolate was detected in all of the tissues of Carica papaya (pawpaw). No other glucosinolates were detected in any tissue of C. papaya. Previous suggestions that indolyl-3-methylglucosinolate might be present could not be confirmed. The highest concentrations of benzylglucosinolate were found in the youngest leaves, but the compound was also detected in leaf stalks, stem internodes and roots. The presence

  14. Effects of naturally occurring glucosides, solasodine glucosides, ginsenosides and parishin derivatives on multidrug resistance of lymphoma cells and leukocyte functions.

    PubMed

    Berek, L; Szabó, D; Petri, I B; Shoyama, Y; Lin, Y H; Molnár, J

    2001-01-01

    Solamargine, solasonine, ginsenosides and parishin-related compounds were investigated for their effects on mdr efflux pump of lymphoma cells, and their effects on T cell proliferative assays and cell mediated immune functions, antibody-dependent cellular cytotoxicity (ADCC) and natural killer (NK) cell activity of human peripheral mononuclear cells. Solamargine and solasonine were the only drugs which inhibited all of the tested immune functions; however, ginsenoside Rc and Rd enhanced T cell proliferative assays and marginally increased the NK cell activity. The majority of the compounds were not able to reverse the multidrug resistance of mouse lymphoma cells. However, ginsenosides Rc, Rd and parishin C were able to moderately reduce the activity of the efflux pump. Parishin, parishin C and crude extract significantly enhanced the ADCC reaction. PMID:11317520

  15. New and known iridoid- and phenylethanoid glycosides from Harpagophytum procumbens and their in vitro inhibition of human leukocyte elastase.

    PubMed

    Boje, Kerstin; Lechtenberg, Matthias; Nahrstedt, Adolf

    2003-09-01

    Ten compounds, harpagoside (1), 8- p-coumaroylharpagide (2), 8-feruloylharpagide (3), 8-cinnamoylmyoporoside (4), pagoside (5), acteoside (6), isoacteoside (7), 6'- O-acetylacteoside (8), cinnamic acid (9) and caffeic acid (10) were isolated from the storage roots of Harpagophytum procumbens, Pedaliaceae. Compounds 1, 2, 6, 7 and 9 are known for H. procumbens; 3 and 10 were isolated the first time from H. procumbens; compounds 4, 5 and 8 are new natural products. Their structures were elucidated using spectroscopic data (NMR, with NOE, COSY and HMBC experiments, UV, [alpha]). The inhibitory activity of aqueous extracts of the roots of H. procumbens and H. zeyheri as well as the main compounds isolated from H. procumbens was tested on human neutrophile elastase. Although inhibition was comparatively weak a dose-dependence was observed. An IC (50) of 542 microg/mL was determined for the aqueous extract of H. procumbens, but 1012 microg/mL for that of H. zeyheri. 6'- O-Acetylacteoside (8), that is not present in H. zeyheri, inhibited the enzyme with an IC (50) of 47 microg/mL (70 microM), compound 7 with 179 microg/mL (286 microM), 2 with 179 microg/mL (331 microM), 5 with 154 microg/mL (260 microM) and 10, which was also used as reference compound, with an IC (50) of 86 microg/mL (475 microM). The IC (50) values of acteoside, harpagoside, cinnamic acid and stachyose were higher than 300 microg/mL and thus not further determined. PMID:14598207

  16. Genetic transformation of Harpagophytum procumbens by Agrobacterium rhizogenes : iridoid and phenylethanoid glycoside accumulation in hairy root cultures

    Microsoft Academic Search

    Renata Gr?bkowska; Aleksandra Królicka; Wojciech Mielicki; Marzena Wielanek; Halina Wysoki?ska

    2010-01-01

    A genetic transformation method using Agrobacterium rhizogenes was developed for Harpagophytum procumbens. The influence of three factors on hairy root formation was tested: bacterial strains (A4 and ATCC 15834), various types\\u000a of explants and acetosyringone (AS) (200 ?M). The highest frequency of transformation (over 50% of explants forming roots\\u000a at the infected sites after 6 weeks of culture on Lloyd and McCown

  17. Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

    PubMed Central

    Zimmermann, Nicole; Hilgraf, Robert; Lehmann, Lutz; Ibarra, Daniel

    2012-01-01

    Summary Starting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1-cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7. PMID:23019455

  18. Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction

    PubMed Central

    Li, Shenghong; Qiu, Shengxiang; Yao, Ping; Sun, Handong; Fong, Harry H. S.; Zhang, Hongjie

    2013-01-01

    As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits of Vitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing an ?, ?-unsaturated ?-lactam moiety. Structurally, they were elucidated to be 9?-hydroxy-13(14)-labden-16,15-amide (2) and 6?-acetoxy-9?-hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8), cis-dihydro-dehydro-diconiferylalcohol-9-O-?-D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4?-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15), ?-sitosterol (16), p-hydroxybenzoic acid (17), and p-hydroxybenzoic acid glucose ester (18). All compound structures were determined/identified on the basis of 1D and/or 2D NMR and mass spectrometry techniques. Compounds 6, 8, 9, and 18 were reported from a Vitex spieces for the first time. The cancer chemopreventive potentials of these isolates were evaluated for NADP(H):quinone oxidoreductase type 1 (QR1) induction activity. Compound 7 demonstrated promising QR1 induction effect, while the new compound vitexlactam (3) was only slightly active. PMID:23662135

  19. Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction.

    PubMed

    Li, Shenghong; Qiu, Shengxiang; Yao, Ping; Sun, Handong; Fong, Harry H S; Zhang, Hongjie

    2013-01-01

    As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits of Vitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing an ? , ? -unsaturated ? -lactam moiety. Structurally, they were elucidated to be 9 ? -hydroxy-13(14)-labden-16,15-amide (2) and 6 ? -acetoxy-9 ? -hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8), cis-dihydro-dehydro-diconiferylalcohol-9-O- ? -D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4'-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15), ? -sitosterol (16), p-hydroxybenzoic acid (17), and p-hydroxybenzoic acid glucose ester (18). All compound structures were determined/identified on the basis of 1D and/or 2D NMR and mass spectrometry techniques. Compounds 6, 8, 9, and 18 were reported from a Vitex spieces for the first time. The cancer chemopreventive potentials of these isolates were evaluated for NADP(H):quinone oxidoreductase type 1 (QR1) induction activity. Compound 7 demonstrated promising QR1 induction effect, while the new compound vitexlactam (3) was only slightly active. PMID:23662135

  20. Rapid characterization and determination of multiple components in Bu-Shen-Yi-Qi-Fang by high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry.

    PubMed

    Nurahmat, Mammat; Chen, Meixia; Luo, Qingli; Ling, Yun; Dong, Jingcheng; Huang, Chenggang

    2014-12-01

    In this study, a qualitative and quantitative analysis using high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry was performed for the quality control of Bu-Shen-Yi-Qi-Fang, a traditional Chinese formula used for asthma. Thirty-four compounds, including flavonoids, isoflavonoids, triterpenoid saponins, and iridoid glycosides were identified or tentatively characterized by comparing their retention times and mass spectra with those of authentic standards or literature data. Sixteen components were considered as the main bioactive constituents of Bu-Shen-Yi-Qi-Fang and they were chosen as the chemical markers in quantitative analysis, including catalpol, leonuride, calycosin-7-O-?-d-glucoside, hyperoside, acteoside, formononetin-7-O-?-D-glucoside, epimedin A, calycosin, icariin, epimedin B, epimedin C, formononetin, astragaloside IV, astragaloside II, baohuoside-I, and astragaloside I. The total run time was 20 min. It was found that the calibration curves for all analytes showed good linearity (R(2) > 0.99) within the test ranges. The relative standard deviations for intra- and inter-day precisions were below 3.9 and 11.7%, respectively. The accuracy was evaluated by the recovery test within the range of 89.20-110.71% with the relative standard deviation < 4.8%. The sample was stable for at least 48 h at 4°C. The results showed that the new approach was effective for the quality control of Bu-Shen-Yi-Qi-Fang. PMID:25216330

  1. Enzymatic synthesis of unsaturated fatty acid glucoside esters for dermo-cosmetic applications.

    PubMed

    Bousquet, M P; Willemot, R M; Monsan, P; Boures, E

    1999-06-20

    Unsaturated fatty acid alpha-butylglucoside esters were prepared by enzymatic esterification of alpha-butylglucoside in nonaqueous media. Conditions were firstly optimized using oleic acid as acyl group. Synthesis was possible in several solvents but the presence of water co-product in the medium limited the reaction to a thermodynamic equilibrium corresponding to a maximal conversion yield of 62%. In pure molten substrates, the removal of water under reduced pressure enabled yields superior to 95% to be obtained. Product profiles depended on enzyme origin : whatever the support, immobilized lipase B from Candida antarctica proved to be far more regioselective for the primary hydroxyl group of glucose than immobilized lipase from Rhizomucor miehei. Results obtained could be easily transposed to the acylation of alpha-butylglucoside with a commercial mixture of unsaturated fatty acids containing more than 60% of linoleic acid. The biocatalyst could be recycled more than ten times without any significant activity loss. PMID:10397830

  2. Acylated cyanidin 3-sophoroside-5-glucoside in purple-violet flowers of Moricandia arvensis (Brassicaceae).

    PubMed

    Tatsuzawa, Fumi; Kato, Kazuhisa; Sato, Motoki; Ito, Shun; Muraoka, Hiroki; Takahata, Yoshihito; Ogawa, Satoshi

    2015-03-01

    A new acylated anthocyanin was isolated as a major pigment, along with a known anthocyanin (Moricandia arvensis anthocyanin 1: MAA-1), from a strain of Moricandia arvensis (Code No. MOR-ARV-3) with purple-violet flowers, and identified as cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(?-glucopyranosyl)-trans-caffeoyl)-?-glucopyranosyl)-trans-sinapoyl)-?-glucopyranoside]-5-O-[6-O-(malonyl)-?-glucopyranoside]. PMID:25924529

  3. Cyanidin and cyanidin 3- O -?-D-glucoside as DNA cleavage protectors and antioxidants

    Microsoft Academic Search

    R. Acquaviva; A. Russo; F. Galvano; G. Galvano; M. L. Barcellona; G. Li Volti; A. Vanella

    2003-01-01

    Anthocyanins, colored flavonoids, are water-soluble pigments present in the plant kingdom; in fact they are secondary plant metabolites responsible for the blue, purple, and red color of many plant tissues. Present in beans, fruits, vegetables and red wines, considerable amounts of anthocyanins are ingested as constituents of the human diet (180–215 mg daily). There is now increasing interest in thein

  4. Mesoporous materials as catalysts for the production of chemicals: Synthesis of alkyl glucosides on MCM-41

    SciTech Connect

    Climent, M.J.; Corma, A.; Iborra, S.; Miquel, S.; Primo, J.; Rey, F. [Univ. Politecnica de Valencia (Spain). Inst. de Tecnologia Quimica] [Univ. Politecnica de Valencia (Spain). Inst. de Tecnologia Quimica

    1999-04-01

    The synthesis of alkylglucosides from glucose and n-butanol has been carried out successfully on Al-MCM-41 mesoporous materials. The influence of the chemical composition (Si/Al) and pore dimensions on activity and selectivity has been studied. It has been found that a higher concentration of acid sites does not guarantee a better catalytic performance, and the adsorption-desorption properties of the material play a determinant role in this reaction where the two reactants and the product have very different polarities. On the other hand, in the range of pore sizes studied here, the larger the diameter of the pore at the same level of Al contents, the more active is the final catalyst. The catalyst loses activity during the process due to the presence of strongly adsorbed molecules. Soxhlet extraction by methanol followed by water does not recover all the initial activity but produces a loss of crystallinity. However, the catalyst could be fully generated by calcination in air at 773 K.

  5. The identification and quantification of steryl glucosides in precipitates from commercial biodiesel

    Technology Transfer Automated Retrieval System (TEKTRAN)

    There have been several experiences of the occurrence of precipitates in manufacturing facilities, transport vessels, and storage tanks containing biodiesel. In some cases these have been formed during storage at temperatures above the cloud point of the fuel. High performance liquid chromatograph...

  6. Prevention of UV-induced carcinogenesis by cyanidin-3-glucoside | Division of Cancer Prevention

    Cancer.gov

    Skip to main content Division of Cancer Prevention Search form Search Main menu Home Major Programs Research Networks Map Alliance of Glycobiologists for Detection of Cancer Barrett's Esophagus Translational Research Network (BETRNet) Cancer Prevention

  7. Treatment of Xerosis with a Topical Formulation Containing Glyceryl Glucoside, Natural Moisturizing Factors, and Ceramide

    PubMed Central

    Kausch, Martina; Rippke, Frank; Schoelermann, Andrea M.; Filbry, Alexander W.

    2012-01-01

    Objective: To assess the effects of Light Formulation, an oil-in-water emulsion, and Rich Formulation, a water-in-oil emulsion, for the treatment of xerosis. Design: Two double-blind, vehicle-controlled trials (both formulations); a double-blind, randomized regression study (Rich Formulation); and a single-blind tolerability study (Light Formulation). The two formulations were applied twice daily for two weeks, for five days in the regression study, and twice daily for two weeks in the tolerability study. Setting: Studies were conducted during winter in Hamburg, Germany. Participants: A total of 169 subjects were enrolled and 154 completed the studies. The majority were between 50 and 80 years of age, women, all with very dry skin. One withdrew because of an incompatibility reaction that reoccurred with the subject's own body lotion after sun exposure. Measurements: Skin hydration and skin barrier function with both formulations over two weeks, long-term moisturization effect after discontinuation of Rich Formulation, and symptom improvement and skin tolerability with Light Formulation. Results: Vehicle-controlled studies of Light and Rich Formulations demonstrated significantly improved hydration at Weeks 1 and 2 versus the untreated site and vehicles, and significantly reduced transepidermal water loss versus untreated site and basic vehicle. Both products significantly decreased visible dryness and tactile roughness. In the regression study, Rich Formulation maintained significant moisturization six days after treatment discontinuation. Light Formulation reduced symptoms of itching, burning, tightness, tingling, and feeling of dryness. Conclusion: These formulations represent a new approach for the treatment of xerosis by addressing multiple key deficiencies in skin hydration. PMID:22916312

  8. Constitutive accumulation of a resveratrol-glucoside in transgenic alfalfa increases resistance to Phoma medicaginis.

    PubMed

    Hipskind, J D; Paiva, N L

    2000-05-01

    Alfalfa (Medicago sativa) was transformed with a peanut (Arachis hypogaea) cDNA encoding resveratrol synthase (RS) transcriptionally regulated by an enhanced Cauliflower mosaic virus (CaMV) 35S promoter. Transgenic plants accumulated a new compound, not present in wild-type or vector-transformed alfalfa, that was identified as trans-resveratrol-3-O-beta-D-glucopyranoside (RGluc) by high-pressure liquid chromatography (HPLC), UV, 1H- and 13C-nuclear magnetic resonance (NMR) analyses. RGluc concentration was highest in the youngest leaves (>15 microg per g fresh weight) and oldest stem internode segments (>10 microg per g fresh weight) while roots contained only trace amounts (<0.2 microg per g fresh weight). RS transcript levels were highest in leaves and stems, with comparatively little transcript accumulation in the roots, while an inverse pattern was observed for chalcone synthase (CHS) transcript levels. CHS directly competes with RS for the metabolic precursors p-coumaroyl CoA and malonyl CoA, and may also contribute to the developmental variations in RGluc levels by limiting the availability of substrates. Agar-plate bioassays indicated that both RGluc and resveratrol greatly inhibit hyphal growth of the alfalfa fungal pathogen Phoma medicaginis. Subsequently, RGluc-containing leaves were wound inoculated and showed a significant reduction (relative to control leaves) in the size of necrotic lesions, intensity of adjacent chlorosis, and number of fungal reproductive structures (pycnidia). Decreasing sporulation of this pathogen may greatly reduce disease spread and severity throughout the field. PMID:10796021

  9. BIOAVAILABILITY OF SOYBEAN ISOFLAVONES FROM AGLYCONE AND GLUCOSIDE FORMS IN AMERICAN WOMEN

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Even though the bioavailability of isoflavones from aglycone forms is believed to be higher than glycosides, human studies testing the bioavailability of isoflavones in Eastern and Western human subjects have been contradictory. To investigate the postprandial absorption and bioavailability of soy ...

  10. Sesquiterpene Glucosides from Anti-leukotriene B4 Release Fraction of Taraxacum Officinale

    Microsoft Academic Search

    Yoshiki Kashiwada; Koichiro Takanaka; Harumi Tsukada; Yoshihisa Miwa; Toru Taga; Shigeo Tanaka; Yasumasa Ikeshiro

    2001-01-01

    Chemical examination of the MeOH extract of the root of Taraxacum officinale, which exhibited inhibitory activity on the formation of leukotriene B4 from activated human neutrophils, has resulted in the isolation of 14-O-?-D-glucosyl-11,13-dihydro-taraxinic acid (1) and 14-O-?-D-glucosyl-taraxinic acid (2). The absolute stereostructure of 1 has been established by X-ray chrystallographic examination.

  11. Distribution of iridiod glucosides and anti-oxidant compounds in Spathodea campanulata parts.

    PubMed

    Elusiyan, C A; Ani, N C; Adewunmi, C O; Olugbade, T A

    2011-01-01

    The antioxidant principles isolated from the various parts of the plant are verminoside (leaf, stem bark and flowers; EC(50) = 2.04 µg/ml), Specioside (flowers; EC(50) = 17.44 µg/ml), Kampeferol diglucoside (leaf; EC(50) = 8.87 µg/ml) and Caffeic acid (leaf and fruits). The non anti-oxidant components isolated in the study include ajugol (stem bark and fruits) and phytol (leaf). PMID:22238480

  12. Transport of Glucose, Gluconate, and Methyl ?-D-Glucoside by Pseudomonas aeruginosa

    PubMed Central

    Guymon, L. F.; Eagon, R. G.

    1974-01-01

    Glucose transport by Pseudomonas aeruginosa was studied. These studies were enhanced by the use of a mutant, strain PAO 57, which was unable to grow on glucose but which formed the inducible glucose transport system when grown in media containing glucose or other inducers such as 2-deoxy-d-glucose. Both PAO 57 and parental strain PAO transported glucose with an apparent Km of 7 ?M. Free glucose was concentrated intracellularly by P. aeruginosa PAO 57 over 200-fold above the external level. These data constitute direct evidence that glucose is transported via active transport by P. aeruginosa. Various experimental data clearly indicated that P. aeruginosa PAO transported methyl ?-d-glucose (?-MeGlc) via the glucose transport system. The apparent Km of ?-MeGlc transport was 7 mM which indicated a 1,000-fold lower affinity of the glucose transport system for ?-MeGlc than for glucose. While only unchanged ?-MeGlc was detected intracellularly in P. aeruginosa, ?-MeGlc was actually concentrated intracellularly less than 2-fold over the external level. Membrane vesicles of P. aeruginosa PAO retained transport activity for gluconate. This solute was concentrated intravesicularly several-fold over the external level. A component of the glucose transport system is believed to have been lost during vesicle preparation since glucose per se was not transported. Instead; glucose was converted to gluconate by membrane-associated glucose dehydrogenase and gluconate was then transported into the vesicles. Although this may constitute an alternate system for glucose transport, it is not a necessary prerequisite for glucose transport by intact cells since P. aeruginosa PAO 57, which lacks glucose dehydrogenase, was able to transport glucose at a rate equal to the parental strain. PMID:4205195

  13. Hepato-protective effects of loganin, iridoid glycoside from Corni Fructus, against hyperglycemia-activated signaling pathway in liver of type 2 diabetic db/db mice.

    PubMed

    Park, Chan Hum; Tanaka, Takashi; Kim, Ji Hyun; Cho, Eun Ju; Park, Jong Cheol; Shibahara, Naotoshi; Yokozawa, Takako

    2011-11-28

    Accumulating evidence indicates that uncontrolled diabetes leads to the progression of diabetic complications such as liver disorder. The present study was carried out to elucidate the protective role of loganin extracted from Corni Fructus against hepatic oxidative stress caused by type 2 diabetes. Loganin (20 or 100mg/kg body weight/day, p.o.) was administered every day for 8 weeks to db/db mice, and its effect was assessed on comparison with vehicle-treated db/db and m/m mice. The administration of loganin led to a decrease in glucose and elevation of leptin in serum. The diabetic oxidative stress was attenuated by loganin through inhibitions of reactive oxygen species production and lipid peroxidation in the serum and liver. The expression of proteins induced by oxidative stress was significantly up-regulated in the liver of diabetic db/db mice; however, the expressions of both Nox-4 and p22(phox) were decreased significantly by loganin administration. Loganin showed a crucial effect in the inflammation-activated signaling pathway through the regulation of NF-?B, COX-2, and iNOS. It was also found to regulate the anti-inflammatory factors Nrf-2 and HO-1 in hepatic tissue. Moreover, expression of MCP-1 was significantly down-regulated in the loganin-treated db/db mice. Furthermore, loganin administration showed a protective effect against apoptosis by the regulation of Bcl-2 and cytochrome c. The present study demonstrated that the administration of loganin isolated from Corni Fructus had a protective effect against hepatic oxidative stress under type 2 diabetes through regulations of protein expressions related to oxidative stress, inflammation, and apoptosis. PMID:21864639

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

    Microsoft Academic Search

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

    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

  15. Specioside ameliorates oxidative stress and promotes longevity in Caenorhabditis elegans.

    PubMed

    Asthana, Jyotsna; Yadav, A K; Pant, Aakanksha; Pandey, Swapnil; Gupta, M M; Pandey, Rakesh

    2015-03-01

    Specioside (6-O-coumaroylcatalpol) is an iridoid glucoside which possesses multifunctional activities viz. analgesic, antidyspeptic, astringent, liver stimulating and wound healing properties. The present study for the first time delineates stress alleviating and lifespan prolonging action of specioside (SPC), isolated from Stereospermum suaveolens in the free living, multicellular nematode model Caenorhabditis elegans. A strong correlation between lifespan extension and stress modulation in adult worms was established in a dose dependent manner. The dietary intake of this phytomolecule elevated juglone induced oxidative and heat induced thermal stress tolerance in C. elegans. On evaluation, it was found that 25 ?M dose of SPC significantly extended lifespan by 15.47% (P?0.0001) with reduction in stress level. Furthermore, SPC enhanced mean survival in mev-1 mutant suggesting its oxidative stress reducing potential. Furthermore, SPC augmented stress modulatory enzymes superoxide dismutase (SOD) and catalase (CAT) level in C. elegans. Altogether, these findings broaden current perspectives concerning stress alleviating potentials of SPC and have implications in development of therapeutics for curing age related disorders. PMID:25619942

  16. Antidiabetic compounds from Sarracenia purpurea used traditionally by the Eeyou Istchee Cree First Nation.

    PubMed

    Muhammad, Asim; Guerrero-Analco, Jose A; Martineau, Louis C; Musallam, Lina; Madiraju, Padma; Nachar, Abir; Saleem, Ammar; Haddad, Pierre S; Arnason, John T

    2012-07-27

    Through ethnobotanical surveys, the CIHR Team in Aboriginal Antidiabetic Medicines identified 17 boreal forest plants stemming from the pharmacopeia of the Cree First Nations of Eeyou Istchee (James Bay region of Northern Quebec) that were used traditionally against diabetes symptoms. The leaves of Sarracenia purpurea (pitcher plant), one of the identified Cree plants, exhibited marked antidiabetic activity in vitro by stimulating glucose uptake in C2C12 mouse muscle cells and by reducing glucose production in H4IIE rat liver cells. Fractionation guided by glucose uptake in C2C12 cells resulted in the isolation of 11 compounds from this plant extract, including a new phenolic glycoside, flavonoid glycosides, and iridoids. Compounds 6 (isorhamnetin-3-O-glucoside), 8 [kaempferol-3-O-(6?-caffeoylglucoside], and 11 (quercetin-3-O-galactoside) potentiated glucose uptake in vitro, which suggests they represent active principles of S. purpurea (EC(50) values of 18.5, 13.8, and 60.5 ?M, respectively). This is the first report of potentiation of glucose uptake by compounds 6 and 8, while compound 11 (isolated from Vaccinium vitis) was previously shown to enhance glucose uptake. Treatment of H4IIE liver cells with the new compound 1, 6'-O-caffeoylgoodyeroside, decreased hepatic glucose production by reducing glucose-6-phosphatase enzymatic activity (IC(50) = 13.6 ?M), which would contribute to lowering glycemia and to the antidiabetic potential of S. purpurea. PMID:22738356

  17. Ochratoxin A-induced DNA damage in human fibroblast: protective effect of cyanidin 3- O-?- d-glucoside

    Microsoft Academic Search

    Alessandra Russo; Luca La Fauci; Rosaria Acquaviva; Agata Campisi; Giuseppina Raciti; Christian Scifo; Marcella Renis; Giacomo Galvano; Angelo Vanella; Fabio Galvano

    2005-01-01

    Ochratoxin A (OTA), a mycotoxin produced by Aspergillus ochraceus and other moulds, has recently received growing attention because of its carcinogenic, teratogenic and nephrotoxic properties in both humans and farm animals. Nevertheless, with regard to the mechanism of toxicity, the data in the literature are inconclusive. The aim of our work was to verify in human fibroblasts treated with different

  18. An on-line method for pressurized hot water extraction and enzymatic hydrolysis of quercetin glucosides from onions.

    PubMed

    Lindahl, Sofia; Liu, Jiayin; Khan, Samiullah; Karlsson, Eva Nordberg; Turner, Charlotta

    2013-06-27

    A novel environmentally sound continuous-flow hot water extraction and enzymatic hydrolysis method for determination of quercetin in onion raw materials was successfully constructed using a stepwise optimization approach. In the first step, enzymatic hydrolysis of quercetin-3,4'-diglucoside to quercetin was optimized using a three level central composite design considering temperature (75-95°C), pH (3-6) and volume concentration of ethanol (5-15%). The enzyme used was a thermostable ?-glucosidase variant (termed TnBgl1A_N221S/P342L) covalently immobilized on either of two acrylic support-materials (Eupergit(®) C 250L or monolithic cryogel). Optimal reaction conditions were irrespective of support 84°C, 5% ethanol and pH 5.5, and at these conditions, no significant loss of enzyme activity was observed during 72 h of use. In a second step, hot water extractions from chopped yellow onions, run at the optimal temperature for hydrolysis, were optimized in a two level design with respect to pH (2.6 and 5.5), ethanol concentration (0 and 5%) and flow rate (1 and 3 mL min(-1)) Obtained results showed that the total quercetin extraction yield was 1.7 times higher using a flow rate of 3 mL min(-1) (extraction time 90 min), compared to a flow rate of 1 mL min(-1) (extraction time 240 min). Presence of 5% ethanol was favorable for the extraction yield, while a further decrease in pH was not, not even for the extraction step alone. Finally, the complete continuous flow method (84°C, 5% ethanol, pH 5.5, 3 mL min(-1)) was used to extract quercetin from yellow, red and shallot onions and resulted in higher or similar yield (e.g. 8.4±0.7 ?mol g(-1) fresh weight yellow onion) compared to a conventional batch extraction method using methanol as extraction solvent. PMID:23764443

  19. New dammarane-type glucosides as potential activators of AMP-activated protein kinase (AMPK) from Gynostemma pentaphyllum.

    PubMed

    Nguyen, Phi Hung; Gauhar, Rehman; Hwang, Seung Lark; Dao, Trong Tuan; Park, Dong Chan; Kim, Ji Eun; Song, Hebok; Huh, Tae Lin; Oh, Won Keun

    2011-11-01

    AMP-activated protein kinase (AMPK) is a key sensor and regulator of glucose, lipid, and energy metabolism throughout the body. Activation of AMPK improves metabolic abnormalities associated with metabolic diseases including obesity and type-2 diabetes. The oriental traditional medicinal herbal plant, Gynostemma pentaphyllum, has shown a wide range of beneficial effects on glucose and lipid metabolism. In this study, we found that G. pentaphyllum contains two novel dammarane-type saponins designated as damulin A (1), 2?,3?,12?-trihydroxydammar-20(22)-E,24-diene-3-O-[?-D-glucopyranosyl-(1?2)-?-D-glucopyranoside], and damulin B (2), 2?,3?,12?-trihydroxydammar-20,24-diene-3-O-[?-D-glucopyranosyl-(1?2)-?-D-glucopyranoside], that strongly activate AMPK in cultured L6 myotube cells. Damulins A and B also increased ?-oxidation and glucose uptake with increasing GluT4 translocation to the plasma membrane in L6 myotube cells. Taken together our results indicate that activation of AMPK by damulins A and B may contribute to beneficial effect of G. pentaphyllum on glucose and lipid metabolism. PMID:21978948

  20. Developing transgenic wheat and barley that exhibit resistance to Fusarium graminearum via glucoside conjugation of trichothecene mycotoxins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Fusarium graminearum infection of wheat and barley results in production of trichothecene mycotoxins including deoxynivalenol (DON) and nivalenol (NIV). These mycotoxins result in increased fungal virulence and reduce grain quality. Numerous transcriptomic studies have been conducted by our lab on t...

  1. Atomistic simulation studies of the ?/?-glucoside and galactoside in anhydrous bilayers: effect of the anomeric and epimeric configurations.

    PubMed

    Ahmadi, Sara; Manickam Achari, Vijayan; Nguan, Hockseng; Hashim, Rauzah

    2014-03-01

    Fully atomistic molecular dynamics simulation studies of thermotropic bilayers were performed using a set of glycosides namely n-octyl-?-D-glucopyranoside (?-C8Glc), n-octyl-?-D-glucopyranoside (?-C8Glc), n-octyl-?-D-galactopyranoside (?-C8Gal), and n-octyl-?-D-galactopyranoside (?-C8Gal) to investigate the stereochemical relationship of the epimeric/anomeric quartet liner glycolipids with the same octyl chain group. The results showed that, the anomeric stereochemistry or the axial/equatorial orientation of C1-O1 (?/?) is an important factor controlling the area and d-spacing of glycolipid bilayer systems in the thermotropic phase. The head group tilt angle and the chain ordering properties are affected by the anomeric effect. In addition, the L(C) phase of ?-C8Gal, is tilting less compared to those in the fluid L(?). The stereochemistry of the C4-epimeric (axial/equatorial) and anomeric (?/?) centers simultaneously influence the inter-molecular hydrogen bond. Thus, the trend in the values of the hydrogen bond for these glycosides is ?-C8Gal?>??-C8Glc?>??-C8Glc?>??-C8Gal. The four bilayer systems showed anomalous diffusion behavior with an observed trend for the diffusion coefficients; and this trend is ?-C8Gal?>??-C8Glc?>??-C8Gal?>??-C8Glc. The "bent" configuration of the ?-anomer results in an increase of the hydrophobic area, chain vibration and chain disorganization. Since thermal energy is dispensed more entropically for the chain region, the overall molecular diffusion decreases. PMID:24623320

  2. Anthocyanins in cones of Abies, Picea, Pinus, Pseudotsuga and Tsuga ( Pinaceae)

    Microsoft Academic Search

    R. J. Griesbach

    2003-01-01

    The anthocyanin content of male and female cones of 27 species of Abies, Picea, Pinus, Pseudotsuga and Tsuga (Pinaceae) was determined. Only four anthocyanins were found: cyanidin 3-glucoside, delphinidin 3-glucoside, peonidin 3-glucoside and petunidin 3-glucoside. Cyanidin 3-glucoside was the major anthocyanin in most of the species analyzed. The methylated anthocyanins (peonidin 3-glucoside and petunidin 3-glucoside) were rare and found in

  3. Regulators of cell division in plant tissues. XXX. Cytokinin metabolism in relation to radish cotyledon expansion and senescence

    Microsoft Academic Search

    D. S. Letham; B. I. Gollnow

    1985-01-01

    Kinetic studies of formation of glucosides of 6-benzylaminopurine (BAP) in excised radish cotyledons indicated that the 3-,\\u000a 7-, and 9-glucosides (N-glucosides) were each formed directly from BAP. The 7- and 9-glucosides of BAP and the 7-glucoside\\u000a of zeatin exhibited great stability in the cotyledons, but the 3-glucoside was converted to free BAP and to the 7- and 9-glucosides\\u000a of BAP.

  4. Flower flavonol and anthocyanin distribution in subgenus Rosa

    Microsoft Academic Search

    Yuki Mikanagi; Masato Yokoi; Yoshihiro Ueda; Norio Saito

    1995-01-01

    In a survey of flower flavonoids in 120 taxa from 10 sections of subgenus Rosa, 19 flavonols and six anthocyanins were detected: six kaempferol (K) glycosides; 3-glucoside (in 99% taxa), 3-rutinoside (63%), 3-sophoroside (60%), 3-rhamnoside (70%), 7-glucoside (94%) and 4?-glucoside (4%); and six quercetin (Q) glycosides: 3-glucoside (91%), 3-glucuronide (62%), 3-rutinoside (63%), 3-sophoroside (69%), 7-glucoside (90%) and 4?-glucoside (4%), and

  5. Journal of Chemical Ecology, Vol. 31, No. 2, February 2005 (C 2005) DOI: 10.1007/s10886-005-1341-1

    E-print Network

    Helsinki, University of

    -005-1341-1 EFFECTS OF QUANTITATIVE VARIATION IN ALLELOCHEMICALS IN Plantago lanceolata ON DEVELOPMENT OF A GENERALIST quantitative variation in allelochemicals (iridoid glycosides) in ribwort plantain, Plantago lanceolata--Chemical defense, iridoid glycosides, Melitaea cinxia, multi- trophic interactions, Plantago lanceolata, Spodoptera

  6. Mulberry anthocyanins, cyanidin 3-rutinoside and cyanidin 3-glucoside, exhibited an inhibitory effect on the migration and invasion of a human lung cancer cell line

    Microsoft Academic Search

    Pei-Ni Chen; Shu-Chen Chu; Hui-Ling Chiou; Wu-Hsien Kuo; Chui-Liang Chiang; Yih-Shou Hsieh

    2006-01-01

    Anthocyanins, present in various fruits and vegetables as natural colorant, have been well characterized to be involved in various bioactive properties and are wildly used for their antioxidant properties. Furthermore, recent studies have revealed pleiotropic anticancer and antiproliferative capabilities of anthocyanin. Berry extract contains high amounts of anthocyanins and is commonly used in diet or in some therapeutic applications. In

  7. cDNA cloning of glycosyltransferases from Chinese wolfberry ( Lycium barbarum L.) fruits and enzymatic synthesis of a catechin glucoside using a recombinant enzyme (UGT73A10)

    Microsoft Academic Search

    Akio Noguchi; Nobuhiro Sasaki; Masahiro Nakao; Harukazu Fukami; Seiji Takahashi; Tokuzo Nishino; Toru Nakayama

    2008-01-01

    To obtain glycosyltransferases that are useful for structural and functional modification of bioactive compounds by glycosylation, an array of cDNAs encoding plant secondary product glycosyltransferases (PSPGs) were cloned from Chinese wolfberry (Lycium barbarum L.) fruits. The cloning strategy was based on high sequence conservation of the C-terminal region of PSPGs. Nine of these cDNAs were heterologously expressed in Escherichia coli,

  8. The Safety and Pharmacokinetics of Cyanidin-3-Glucoside after 2-Week Administration of Black Bean Seed Coat Extract in Healthy Subjects

    PubMed Central

    Jeon, Sangil; Han, Seunghoon; Lee, Jongtae; Hong, Taegon

    2012-01-01

    We analyzed the pharmacokinetics of C3G on data from twelve subjects, after 2-week multiple dosing of black bean (Phaseolus vulgaris, Cheongjakong-3-ho) seed coat extract, using the mixed effect analysis method (NONMEM, Ver. 6.2), as well as the conventional non-compartmental method. We also examined the safety and tolerability. The PK analysis used plasma concentrations of the C3G on day 1 and 14. There was no observed accumulation of C3G after 2-week multiple dosing of black bean seed coat extract. The typical point estimates of PK were CL (clearance)=3,420 l/h, V (volume)=7,280 L, Ka (absorption constant)=9.94 h-1, ALAG (lag time)=0.217 h. The black bean seed coat extract was well tolerated and there were no serious adverse events. In this study, we confirmed that a significant amount of C3G was absorbed in human after given the black bean seed coat extract. PMID:22915990

  9. 12-Hydroxyjasmonic Acid Glucoside Is a COI1-JAZ-Independent Activator of Leaf-Closing Movement in Samanea saman1[OA

    PubMed Central

    Nakamura, Yoko; Mithöfer, Axel; Kombrink, Erich; Boland, Wilhelm; Hamamoto, Shin; Uozumi, Nobuyuki; Tohma, Kentaro; Ueda, Minoru

    2011-01-01

    Jasmonates are ubiquitously occurring plant growth regulators with high structural diversity that mediate numerous developmental processes and stress responses. We have recently identified 12-O-?-d-glucopyranosyljasmonic acid as the bioactive metabolite, leaf-closing factor (LCF), which induced nyctinastic leaf closure of Samanea saman. We demonstrate that leaf closure of isolated Samanea pinnae is induced upon stereospecific recognition of (?)-LCF, but not by its enantiomer, (+)-ent-LCF, and that the nonglucosylated derivative, (?)-12-hydroxyjasmonic acid also displays weak activity. Similarly, rapid and cell type-specific shrinkage of extensor motor cell protoplasts was selectively initiated upon treatment with (?)-LCF, whereas flexor motor cell protoplasts did not respond. In these bioassays related to leaf movement, all other jasmonates tested were inactive, including jasmonic acid (JA) and the potent derivates JA-isoleucine and coronatine. By contrast, (?)-LCF and (?)-12-hydroxyjasmonic acid were completely inactive with respect to activation of typical JA responses, such as induction of JA-responsive genes LOX2 and OPCL1 in Arabidopsis (Arabidopsis thaliana) or accumulation of plant volatile organic compounds in S. saman and lima bean (Phaseolus lunatus), generally considered to be mediated by JA-isoleucine in a COI1-dependent fashion. Furthermore, application of selective inhibitors indicated that leaf movement in S. saman is mediated by rapid potassium fluxes initiated by opening of potassium-permeable channels. Collectively, our data point to the existence of at least two separate JA signaling pathways in S. saman and that 12-O-?-d-glucopyranosyljasmonic acid exerts its leaf-closing activity through a mechanism independent of the COI1-JAZ module. PMID:21228101

  10. Leloir Glycosyltransferases and Natural Product Glycosylation: Biocatalytic Synthesis of the C-Glucoside Nothofagin, a Major Antioxidant of Redbush Herbal Tea

    PubMed Central

    Bungaruang, Linda; Gutmann, Alexander; Nidetzky, Bernd

    2013-01-01

    Nothofagin is a major antioxidant of redbush herbal tea and represents a class of bioactive flavonoid-like C-glycosidic natural products. We developed an efficient enzymatic synthesis of nothofagin based on a one-pot coupled glycosyltransferase-catalyzed transformation that involves perfectly selective 3?-C-?-d-glucosylation of naturally abundant phloretin and applies sucrose as expedient glucosyl donor. C-Glucosyltransferase from Oryza sativa (rice) was used for phloretin C-glucosylation from uridine 5?-diphosphate (UDP)-glucose, which was supplied continuously in situ through conversion of sucrose and UDP catalyzed by sucrose synthase from Glycine max (soybean). In an evaluation of thermodynamic, kinetic, and stability parameters of the coupled enzymatic reactions, poor water solubility of the phloretin acceptor substrate was revealed as a major bottleneck of conversion efficiency. Using periodic feed of phloretin controlled by reaction progress, nothofagin concentrations (45?mM; 20?g?l?1) were obtained that vastly exceed the phloretin solubility limit (5–10?mM). The intermediate UDP-glucose was produced from catalytic amounts of UDP (1.0?mM) and was thus recycled 45 times in the process. Benchmarked against comparable glycosyltransferase-catalyzed transformations (e.g., on quercetin), the synthesis of nothofagin has achieved intensification in glycosidic product formation by up to three orders of magnitude (?M?mM range). It thus makes a strong case for the application of Leloir glycosyltransferases in biocatalytic syntheses of glycosylated natural products as fine chemicals. PMID:24415961

  11. Development of an in vivo glucosylation platform by coupling production to growth: Production of phenolic glucosides by a glycosyltransferase of Vitis vinifera.

    PubMed

    De Bruyn, Frederik; De Paepe, Brecht; Maertens, Jo; Beauprez, Joeri; De Cocker, Pieter; Mincke, Stein; Stevens, Christian; De Mey, Marjan

    2015-08-01

    Glycosylation of small molecules can significantly alter their properties such as solubility, stability, and/or bioactivity, making glycosides attractive and highly demanded compounds. Consequently, many biotechnological glycosylation approaches have been developed, with enzymatic synthesis and whole-cell biocatalysis as the most prominent techniques. However, most processes still suffer from low yields, production rates and inefficient UDP-sugar formation. To this end, a novel metabolic engineering strategy is presented for the in vivo glucosylation of small molecules in Escherichia coli W. This strategy focuses on the introduction of an alternative sucrose metabolism using sucrose phosphorylase for the direct and efficient generation of glucose 1-phosphate as precursor for UDP-glucose formation and fructose, which serves as a carbon source for growth. By targeted gene deletions, a split metabolism is created whereby glucose 1-phosphate is rerouted from the glycolysis to product formation (i.e., glucosylation). Further, the production pathway was enhanced by increasing and preserving the intracellular UDP-glucose pool. Expression of a versatile glucosyltransferase from Vitis vinifera (VvGT2) enabled the strain to efficiently produce 14 glucose esters of various hydroxycinnamates and hydroxybenzoates with conversion yields up to 100%. To our knowledge, this fast growing (and simultaneously producing) E. coli mutant is the first versatile host described for the glucosylation of phenolic acids in a fermentative way using only sucrose as a cheap and sustainable carbon source. Biotechnol. Bioeng. 2015;112: 1594-1603. © 2015 Wiley Periodicals, Inc. PMID:25728421

  12. Quercetin Glucosides Interact With the Intestinal Glucose Transport Pathway 1 1 This work was supported by a UK Biotechnology and Biological Sciences Research Council Competitive Strategic Grant

    Microsoft Academic Search

    Jennifer M Gee; M. Susan DuPont; Michael J. C Rhodes; Ian T Johnson

    1998-01-01

    Flavonols are efficient antioxidants with the potential to protect biological macromolecules from oxidative damage in vivo, and if absorbed into the circulation they may protect against cardiovascular disease. Although flavonol aglycones are present in foods at low concentrations, their glycosides are abundant in onions, apples, beans and tea, and are thought to be stable under the conditions of the human

  13. Isolation of a novel flavanone 6-glucoside from the flowers of Carthamus tinctorium (Honghua) by high-speed counter-current chromatography.

    PubMed

    Zhao, Mingbo; Ito, Yoichiro; Tu, Pengfei

    2005-10-01

    A novel flavanone glycoside, (2S)-4',5,6,7-tetrahydroxyflavavone 6-O-beta-D-glucopyranoside was isolated from the ethyl acetate extract of the flowers of Carthamus tinctorium by high-speed counter-current chromatography (HSCCC). Using an optimized two-phase solvent system composed of ethyl acetate-methanol-water (5:1:5, v/v), target compound (52 mg) with purity of 98.0% was obtained from 2.0 g of sample by HSCCC in seven times run. The structure of the target compound was elucidated by means of spectroscopic methods including IR, MS, 1D and 2D NMR techniques. PMID:16196150

  14. Isolation of a novel flavanone 6-glucoside from the flowers of Carthamus tinctorium (Honghua) by high-speed counter-current chromatography

    Microsoft Academic Search

    Mingbo Zhao; Yoichiro Ito; Pengfei Tu

    2005-01-01

    A novel flavanone glycoside, (2S)-4?,5,6,7-tetrahydroxyflavavone 6-O-?-d-glucopyranoside was isolated from the ethyl acetate extract of the flowers of Carthamus tinctorium by high-speed counter-current chromatography (HSCCC). Using an optimized two-phase solvent system composed of ethyl acetate–methanol–water (5:1:5, v\\/v), target compound (52mg) with purity of 98.0% was obtained from 2.0g of sample by HSCCC in seven times run. The structure of the target

  15. 4'-Demethyl-deoxypodophyllotoxin glucoside isolated from Podophyllum hexandrum exhibits potential anticancer activities by altering Chk-2 signaling pathway in MCF-7 breast cancer cells.

    PubMed

    Zilla, Mahesh K; Nayak, Debasis; Amin, Hina; Nalli, Yedukondalu; Rah, Bilal; Chakraborty, Souneek; Kitchlu, Surender; Goswami, Anindya; Ali, Asif

    2014-10-18

    We investigated the root of Podophyllum hexandrum as a potential source of lead bioactive metabolites with anticancer activity. The present study led to the isolation of six known aryltetralin-type lignans designated as 4'-demethyl-deoxypodophyllotoxin (1), podophyllotoxin (2), 4'-demethyl-podophyllotoxin (3), podophyllotoxin-4-O-?-d-glucopyranoside (4), 4'-demethyl-deoxypodophyllotoxin-4-O-?-d-glucopyranoside (5), 4'-demethyl-podophyllotoxin-4-O-?-d-glucopyranoside (6), along with three known flavones Kaempferol (7), Quercetin (8), Astragalin (9) from the root of P. hexandrum. Compounds (1-9) exhibited the remarkable cytotoxic potential in diverse cancer cell lines. 5 therapeutic potential was extensively studied first time which exhibiting antiproliferative and ROS generating activity than its non-glycoside analogue 1. Furthermore, 5 augmented the apoptotic cascades in MCF-7 breast cancer cells, viz. nuclear condensation, membrane blebbing, probably by destabilizing the micro-tubular protein tubulin. Strikingly, our docking study and in vitro assays demonstrate that 5 binds to and modulate checkpoint kinase-2, a key cell cycle regulatory protein in normal and cancer cells. PMID:25446499

  16. Accumulation of brachycerine, an antioxidant glucosidic indole alkaloid, is induced by abscisic acid, heavy metal, and osmotic stress in leaves of Psychotria brachyceras.

    PubMed

    do Nascimento, Naíla Cannes; Menguer, Paloma Koprovski; Henriques, Amélia Teresinha; Fett-Neto, Arthur Germano

    2013-12-01

    Psychotria brachyceras Muell. Arg. produces the antioxidant monoterpene indole alkaloid (MIA) brachycerine, which, besides retaining a glucose residue, has its terpenoid moiety derived not from secologanin, but probably from epiloganin, representing a new subclass of MIAs. In this work we showed that osmotic stress agents, such as sodium chloride, sorbitol and polyethylene glycol (PEG), induced brachycerine accumulation in leaf disks of P. brachyceras. Other oxidative stress inducers, such as exposure to aluminum and silver, also increased brachycerine content. Abscisic acid (ABA) treatment was shown to increase brachycerine yield, suggesting its involvement in brachycerine induction during osmotic stress. Ascorbate peroxidase activity was induced in PEG-treated leaf disks, whereas superoxide dismutase (SOD) activity remained unaltered. Assays with specific inhibitors of the cytosolic mevalonate (MVA) and plastidic 2-C-methyl-D-erythritol 4-phosphate (MEP) pathways showed that the terpenoid moiety of brachycerine derived predominantly from the MEP pathway. These results suggest a potential involvement of brachycerine in plant defense against osmotic/oxidative stress damage, possibly contributing to detoxification of hydroxyl radical and superoxide anion as a SOD-like molecule. PMID:24045228

  17. Quantitation of multiple mycotoxins and cyanogenic glucosides in cassava samples from Tanzania and Rwanda by an LC-MS/MS-based multi-toxin method.

    PubMed

    Sulyok, M; Beed, F; Boni, S; Abass, A; Mukunzi, A; Krska, R

    2015-01-01

    A multi-mycotoxin method based on liquid chromatography/tandem mass spectrometry (LC-MS/MS) was used for a mycotoxin survey in 627 samples of processed cassava collected from different districts across Tanzania and Rwanda after the method performance for this matrix had been determined. Matrix effects as well as extraction efficiencies were found to be similar to most other previously investigated matrices with the exception of distinct matrix effects in the negative ionisation mode for early eluting compounds. Limits of detection were far below the regulatory limits set in the European Union for other types of commodities. Relative standard deviations were generally lower than 10% as determined by replicates spiked on two concentration levels. The sample-to-sample variation of the apparent recoveries was determined for 15 individually spiked samples during three different analytical sequences. The related standard deviation was found to be lower than 15% for most of the investigated compounds, thus confirming the applicability of the method for quantitative analysis. The occurrence of regulated mycotoxins was lower than 10% (with the exception of zearalenone) and the related limits were exceeded only in few samples, which suggests that cassava is a comparatively safe commodity as regards mycotoxins. The most prevalent fungal metabolites were emodin, kojic acid, beauvericin, tryptophol, 3-nitropropionic acid, equisetin, alternariol methylether, monocerin, brevianamide F, tenuazonic acid, zearalenone, chrysophanol, monilifomin, enniatins, apicidin and macrosporin. The related concentrations exceeded 1 mg kg(-1) only in few cases. However, extremely high levels of cyanogenic plant toxins, which had been previously added to the method, were observed in few samples, pointing out the need for improved post-harvest management to decrease the levels of these compounds. PMID:25350522

  18. A 7-Deoxyloganetic Acid Glucosyltransferase Contributes a Key Step in Secologanin Biosynthesis in Madagascar Periwinkle[C][W][OPEN

    PubMed Central

    Asada, Keisuke; Salim, Vonny; Masada-Atsumi, Sayaka; Edmunds, Elizabeth; Nagatoshi, Mai; Terasaka, Kazuyoshi; Mizukami, Hajime; De Luca, Vincenzo

    2013-01-01

    Iridoids form a broad and versatile class of biologically active molecules found in thousands of plant species. In addition to the many hundreds of iridoids occurring in plants, some iridoids, such as secologanin, serve as key building blocks in the biosynthesis of thousands of monoterpene indole alkaloids (MIAs) and many quinoline alkaloids. This study describes the molecular cloning and functional characterization of three iridoid glucosyltransfeases (UDP-SUGAR GLYCOSYLTRANSFERASE6 [UGT6], UGT7, and UGT8) from Madagascar periwinkle (Catharanthus roseus) with remarkably different catalytic efficiencies. Biochemical analyses reveal that UGT8 possessed a high catalytic efficiency toward its exclusive iridoid substrate, 7-deoxyloganetic acid, making it better suited for the biosynthesis of iridoids in periwinkle than the other two iridoid glucosyltransfeases. The role of UGT8 in the fourth to last step in secologanin biosynthesis was confirmed by virus-induced gene silencing in periwinkle plants, which reduced expression of this gene and resulted in a large decline in secologanin and MIA accumulation within silenced plants. Localization studies of UGT8 using a carborundum abrasion method for RNA extraction show that its expression occurs preferentially within periwinkle leaves rather than in epidermal cells, and in situ hybridization studies confirm that UGT8 is preferentially expressed in internal phloem associated parenchyma cells of periwinkle species. PMID:24104568

  19. Anthocyanins and flavonoids from shredded red onion and changes during storage in perforated films

    Microsoft Academic Search

    Federico Ferreres; María I. Gil; Francisco A. Tomás-Barberán

    1996-01-01

    From the edible parts of the Spanish red onion (cultivar ‘Morada de Amposta’), the anthocyanins cyanidin 3-glucoside, cyanidin 3-arabinoside, cyanidin 3-malonyl-glucoside and cyanidin 3-malonylarabinoside and the flavonoids quercetin 3,4?-diglucoside, quercetin 7,4?-diglucoside, quercetin 3-glucoside, dihydro-quercetin 3-glucoside and isorhamnetin 4?-glucoside were identified. The amount of anthocyanins reached 233 mg kg?1 and that of the flavonoids 943 mg kg?1 fresh weight of onions.

  20. Release of Active Cytokinin by a beta-Glucosidase Localized to the Maize Root Meristem

    Microsoft Academic Search

    Bretislav Brzobohaty; Ian Moore; Peter Kristoffersen; Laszlo Bako; Narciso Campos; Jeff Schell; Klaus Palme

    1993-01-01

    A beta-glucoside encoded by a cloned Zea mays complementary DNA (Zm-p60. 1) cleaved the biologically inactive hormone conjugates cytokinin-O-glucosides and kinetin-N3glucoside, releasing active cytokinin. Tobacco protoplasts that transiently expressed Zm-p60.1 could use the inactive cytokinin glucosides to initiate cell division. The ability of protoplasts to sustain growth in response to cytokinin glucosides persisted indefinitely after the likely disappearance of the

  1. 5- O-glucosyldihydroflavones from the leaves of Helicia cochinchinensis

    Microsoft Academic Search

    Ken-Ichi Morimura; Asuka Gatayama; Reiki Tsukimata; Katsuyoshi Matsunami; Hideaki Otsuka; Eiji Hirata; Takakazu Shinzato; Mitsunori Aramoto; Yoshio Takeda

    2006-01-01

    From the leaves of Helicia cochinchinensis, collected on Okinawa Island, seven phenolic glucosides and two terpenic glucosides were isolated. Five of the phenolic glucosides were previously known, being identified with p-coumaric and ferulic acids glucosyl esters, rhodioloside, helicidiol, and naringenin 5-O-?-d-glucopyranoside. The structures of two other phenolic glucosides, named heliciosides A and B, were elucidated to be 5-O-?-d-glucosides of 3-hydroxyflavanone,

  2. The Effects of Plantago major on the Activation of the Neutrophil Respiratory Burst.

    PubMed

    Reina, Elaine; Al-Shibani, Nouf; Allam, Eman; Gregson, Karen S; Kowolik, Michael; Windsor, L Jack

    2013-10-01

    Plantago major is a common plant that grows worldwide in temperate zones and is found in fields, lawns, and on the roadsides. Its leaves and seeds have been used in almost all parts of the world for centuries as a wound healer, analgesic, antioxidant, and antibiotic, as well as an immune system modulator, antiviral, antifungal, and anti-inflammatory agent. Baicalein and aucubin are the two most biologically active components of P. major, and both have been shown to have antioxidant, anti-inflammatory, and anticancer properties. Neutrophils have a pivotal role in wound healing and inflammation. Their principal mechanism of host defense is the killing of pathogens via the production of reactive oxygen species (ROS). The aim of the present study was to determine the in vitro effects of P. major extract, baicalein, and aucubin on human neutrophil respiratory burst activity. The cytotoxicity of the agents was assessed by lactate dehydrogenase (LDH) assays. A standard luminol-dependent chemiluminescence (CL) assay was utilized to monitor the respiratory burst of the neutrophils after exposure to P. major extract and its two active ingredients, baicalein and aucubin. Three replicates per group were included in each of the three runs of the experiments and analysis of variance (ANOVA) was used for statistical analysis. P. major and baicalein were not toxic to the cells at any of the concentrations examined. Aucubin was toxic to the cells only at the highest concentration tested (P = 0.0081). However, genistein was toxic to the cells at all of the concentrations examined except for the lowest concentration of 16.9 ?g/ml (P = 0.985). P. major (-0.10 ± 0.11), aucubin (0.06 ± 0.16), baicalein (-0.10 ± 0.11), and genistein (-0.18 ± 0.07) all significantly (P < 0.0001) inhibited ROS production from the neutrophils. P. major extract inhibited neutrophil ROS production, as did aucubin and baicalein. Therefore, these components should be investigated further with relation to the regulation of destructive ROS production in conditions such as periodontal disease. PMID:24716188

  3. [Dihydropenstemide from Penstemon confertus and the Preparation of epi-Dihydropenstemide from Penstemide.].

    PubMed

    Gering, B; Junior, P; Wichtl, M

    1986-10-01

    From leaves of PENSTEMON CONFERTUS Dougl. a valeriana-type ester iridoid has been isolated and structurally elucidated as dihydropenstemide by spectroscopic methods. Catalytic hydrogenation of penstemide provides a new compound, identified as 8- EPI-dihydropenstemide. PMID:17345338

  4. Thermal Degradation Kinetics of Three Kinds of Representative Anthocyanins Obtained from Blood Orange

    Microsoft Academic Search

    Liang LIU; Shao-qian CAO; Si-yi PAN

    2011-01-01

    Cyanidin-3-glucoside, cyanidin-3-(6?-malonyl)-glucoside, and cyanidin-3-glucoside-derived pyranoanthocyanins which were three major anthocyanins of blood orange, were obtained using a Toyopearl TSK HW-40S column chromatography. Then, thermal degradation kinetics of the three major anthocyanins was studied at selected temperatures (70, 80, and 90°C). Degradation parameters such as k and t1\\/2 values were determined. The activation energy (Ea) values for cyanidin-3-glucoside, cyanidin-3-(6?-malonyl)-glucoside and cyanidin-3-glucoside-derived

  5. Uridine 5?-diphosphate-xylose: anthocyanidin 3-O-glucose-xylosyltransferase from petals of Matthiola incana R.Br

    Microsoft Academic Search

    M. Teusch

    1986-01-01

    Petals of genetically defined lines of Matthiola incana R.Br. contain a glycosyltransferase which catalyzes the transfer of the xylosyl moiety of uridine 5'-diphosphate-xylose to the glucose of cyanidin 3-glucoside. The enzyme also uses 3-glucosides of pelargonidin and delphinidin, cyanidin 3-(p-coumaroyl)-glucoside and 3-(caffeoyl)-glucoside as substrates. The xylosyltransferase exhibits a pH optimum of 6.5. The enzyme activity depends on the stage of

  6. Polyphenolic constituents of blackcurrant seed residue

    Microsoft Academic Search

    Yinrong Lu; L Yeap Foo

    2003-01-01

    Chemical investigation of blackcurrant seed residue from oil extraction revealed the presence of an array of polyphenols which were dominated by four anthocyanins consisting of the rutinosides and glucosides of delphinidin and cyanidin. Also isolated were the glucosides and rutinosides of myricetin and quercetin, kaempferol-3-glucoside, dihydroquercetin and aureusidin, as well as the phenolic acids 1-cinnamoyl- and 1-p-coumaroyl-?-d-glucosides. This is the

  7. Withanolides from Withania somnifera roots

    Microsoft Academic Search

    Laxminarain Misra; Priyanka Mishra; Archana Pandey; Rajender S. Sangwan; Neelam S. Sangwan; Rakesh Tuli

    2008-01-01

    Two new and seven known withanolides along with ?-sitosterol, stigmasterol, ?-sitosterol glucoside, stigmasterol glucoside, ?+? glucose were isolated from the roots of Withania somnifera. Among the known compounds, Viscosa lactone B, stigmasterol, stigmasterol glucoside and ?+? glucose are being reported from the roots of W. somnifera for the first time. One of the new compounds contained the rare 16?-acetoxy-17(20)-ene the

  8. Using reversed phase high performance liquid chromatography to study the complexation of anthocyanins with ?-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Deineka, V. I.; Lapshova, M. S.; Deineka, L. A.

    2014-06-01

    It is shown by means of reversed phase high performance liquid chromatography (RP HPLC) with mobile phases containing additions of ?-cyclodextrin that 5-glucosides of cyanidin and pelargonidin form stronger inclusion complexes than 3-glucosides; this is explained by the steric interference of the glucoside radical.

  9. Host Preference and Larval Performance of the Salicylate-Using Leaf Beetle Phratora vitellinae

    Microsoft Academic Search

    Nathan E. Rank; Alfred Kopf; Riitta Julkunen-Tiitto; Jorma Tahvanainen

    1998-01-01

    Larvae of Phratora vitellinae (Coleoptera: Chrysomelidae) convert salicyl glucosides from the host plant into a larval defensive secretion with salicylaldehyde. This secretion repels generalist predators. Willows vary greatly in the concentrations of salicyl glucosides in their leaves. One may predict that P. vitellinae prefers and survives better on plants that contain more salicyl glucosides. We determined the amount of larval

  10. Anthocyanin cyanidin-3-O-beta-glucoside, a flavonoid, increases hepatic glutathione synthesis and protects hepatocytes against reactive oxygen species during hyperglycemia: involvement of a cAMP-PKA dependent signaling pathway

    Microsoft Academic Search

    Wei Zhu; Qianju Jia; Yun Wang; Yuhua Zhang; Min Xia

    Enhanced oxidative stress, due to high glucose, contributes to the pathological changes in diabetic-related liver complications. Reducing oxidative stress may alleviate these pathogenic processes. Anthocyanin, a natural antioxidant, has been reported to reduce intracellular reactive oxygen species (ROS) levels but the mechanism of this reduction is not fully understood. The glutathione antioxidant system is critical for counteracting oxidative stress-induced intracellular

  11. Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot ( Allium cepa L.)

    Microsoft Academic Search

    S. Masuzaki; M. Shigyo; N. Yamauchi

    2006-01-01

    The extrachromosome 5A of shallot (Allium cepa L., genomes AA) has an important role in flavonoid biosynthesis in the scaly leaf of Allium fistulosum–shallot monosomic addition lines (FF+nA). This study deals with the production and biochemical characterisation of A. fistulosum–shallot multiple alien addition lines carrying at least 5A to determine the chromosomal locations of genes for quercetin\\u000a formation. The multiple

  12. 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

  13. Anthocyanins and other flavonoids as flower pigments from eleven Centaurea species.

    PubMed

    Mishio, Tamaki; Takeda, Kosaku; Iwashina, Tsukasa

    2015-03-01

    Anthocyanins and other flavonoids were isolated from the flowers of eleven Centaurea species, C. macrocephala, C. rupestotilis and C. suaveolens, which produce yellow flowers, and C. achtarovii, C. dealbata, C. montana, C. nigra, C. scabiosa, C. simplicicaulis, C. hypoleuca and C. triumfetti, which have cyanic flowers. Four anthocyanins, cyanidin 3,5-di-O-glucoside, cyanidin 3-O-(6"-malonylglucoside)-5-O-glucoside, cyanidin 3-O-(6"-succinylglucoside)-5- O-glucoside and cyanidin glycoside, were detected in the cyanic flowers of seven Centaurea species. Of these anthocyanins, the first two were found as major anthocyanins. In the cyanic species, four other flavonoids, apigenin 7-O-glucuronide-4'-O-glucoside, malonylated apigenin 7,4'-di-O-glucoside, apigenin 7-0- glucuronide and kaempferol glycoside, were also isolated. On the other hand, nine flavonols and four flavones were isolated from the three yellow-flowered species, and identified as quercetagetin, quercetagetin 7-O-glucoside, quercetagetin 3'-methyl ether 7-O-glucoside, patuletin, patuletin 7-O-glucoside, quercetin 7-O-glucoside, kaempferol 3-methyl ether, kaempferol 3-methyl ether 4'-O-glucuronide and isorhamnetin 3-O-galactoside, and apigenin, apigenin 7- O-glucuronide, luteolin 7-O-glucoside and apigenin 6,8-di-C-glucoside (vicenin-2). Of these flavonoids, the former five flavonols are "yellow flavonols", and it was shown that their flower colors are due to these compounds. PMID:25924526

  14. Flavonoids and phenylpropanoid derivatives from Campanula barbata.

    PubMed

    Cuendet, M; Potterat, O; Hostettmann, K

    2001-03-01

    Four new phenylpropanoid derivatives, barbatosides A-D, and a new catechin, barbatoflavan, were isolated from the whole plant of Campanula barbata L. (Campanulaceae) and identified as wahlenbergioside-3'-O-glucoside, wahlenbergioside-3'-O-(2'''-(p-methoxycinnamoyl))-glucoside, wahlenbergioside-3'-O-(4'''-(trans-p-coumaroyl))-glucoside, wahlenbergioside-3'-O-(4"'-(cis-p-coumaroyl))-glucoside and 3-acetyl-5-methoxy-7,3',4'-trihydroxy-8-O-glucoside-flavan-3-ol, respectively, by spectroscopic methods. In addition, four flavonols were isolated and identified as kaempferol-3-O-glucoside, kaempferol-3-O-rutinoside, quercetin-3-O-glucoside and quercetin-3-O-rutinoside. Barbatoflavan demonstrated scavenging properties towards the DPPH radical. PMID:11281141

  15. 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

  16. Isolation, identification, and antioxidant activity of anthocyanin compounds in Camarosa strawberry

    Microsoft Academic Search

    Ana B. Cerezo; Elyana Cuevas; P. Winterhalter; M. C. Garcia-Parrilla; A. M. Troncoso

    2010-01-01

    This paper explores the bioactive composition of strawberry (Camarosa variety) [Fragaria ×ananassa (Rosaceae Family)] describing its anthocyanin composition and measuring the antioxidant activity (AA) of isolated pigments.Pelargonidin-3-glucoside was the major compound followed by pelargonidin-3-rutinoside and 11 pelargonidin and cyanidin derivatives, determined by LC–DAD–MS. Additionally, delphinidin-3-glucoside, peonidin-3-glucoside, and cyanidin-3-galactoside were tentatively identified for the first time in strawberry. Another original contribution

  17. Anthocyanins in Fruits of Passiflora edulisand P. suberosa

    Microsoft Academic Search

    Linda Kidøy; Anne Mette Nygård; Øyvind M. Andersen; Atle T. Pedersen; Dagfinn W. Aksnes; Bernard T. Kiremire

    1997-01-01

    The analysis of anthocyanin pigments in the passion fruitPassiflora edulisand in the highly colored fruits ofP. suberosawas performed using combinations of chromatographic and spectroscopic techniques. In addition to cyanidin 3-glucoside (97%), small amounts of cyanidin 3-(6?-malonylglucoside) (2%) and pelargonidin 3-glucoside (1%) were found in the rind of the passion fruit. The 3-(6?-malonylglucoside) and 3-glucoside of cyanidin, delphinidin, petunidin, and pelargonidin

  18. Hepatoprotective and free radical scavenging activities of phenolic petrosins and flavonoids isolated from Equisetum arvense

    Microsoft Academic Search

    Hyuncheol Oh; Do-Hoon Kim; Jung-Hee Cho; Youn-Chul Kim

    2004-01-01

    Hepatoprotective activity-guided fractionation of the MeOH extract of Equisetum arvense L. (Equisetaceae) resulted in the isolation of two phenolic petrosins, onitin (1) and onitin-9-O-glucoside (2), along with four flavonoids, apigenin (3), luteolin (4), kaempferol-3-O-glucoside (5), and quercetin-3-O-glucoside (6). Among these, compounds 1 and 4 exhibited hepatoprotective activities on tacrine-induced cytotoxicity in human liver-derived Hep G2 cells, displaying EC50 values of

  19. 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

  20. Flavonoids of Arctostaphylos uva-ursi (Ericaceae)

    Microsoft Academic Search

    K. E. Denford

    1973-01-01

    Résumé Dans trois variétés d'Arctostaphylos uva-ursi, j'ai trouvé les flavanoides suivants: arabinoside-3, glucoside-3, galactoside-3, diglucoside-3, rutinoside-3, rhamnoside-3, glucoside-7-quercetine and arabinoside-3, glucoside-3-myricetine. J'ai déduit une corrélation entre la distribution limitée de certains d'entre ces flavonoides et les localités, en Amérique du Nord qui ont échappé a la glaciation.

  1. Hemolytic action and surface activity of triterpene saponins from Anchusa officinalis L. Part 21: On the costituents of Boraginaceae.

    PubMed

    Romussi, G; Cafaggi, S; Bignardi, G

    1980-08-01

    Relationship between chemical structure, hemolytic action and surface activity of five glucosides of oleanolic acid were studied. Monodesmosidic saponins are more hemolytic than bisdesmosidic. The hemolytic activity of monodesmosides decreased with the length and the branching of the glucosidic chain. Surface activity is major in bisdesmosides. This property increases with the length of the glucosidic chain in monodesmosides. Increase of hemolytic action is accompanied by a decrease of surface activity. PMID:7433502

  2. Effect of isoorientin isolated from Arum palaestinum on uterine smooth muscle of rats and guinea pigs

    Microsoft Academic Search

    F. U Afifi; E Khalil; S Abdalla

    1999-01-01

    The phytochemical investigation of Arum palaestinum resulted in the isolation of two flavone C-glucosides, namely isoorientin (luteolin 6-C-glucoside) and vitexin (apigenin 8-C glucoside). The effects of isoorientin on rat isolated aorta, ileum, trachea and uterus and on guinea-pig uterus were studied. Isoorientin (10?7M–6×10?4M) caused concentration-dependent inhibition of the amplitude and the frequency of the phasic contractions of the rat and

  3. 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

  4. Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens

    Microsoft Academic Search

    Hiroyuki Fujiwara; Yoshikazu Tanaka; Yuko Fukui; Toshihiko Ashikari; Masaatsu Yamaguchi; Takaaki Kusumi

    1998-01-01

    Hydroxycinnamoyl-CoA:anthocyanin 3-O-glucoside-6??-O-hydroxycinnamoyltransferase (3AT; EC 2.3.1.-) was identified and highly purified from red leaves of Perilla frutescens, which accumulate cyanidin 3-(6-O-p-coumaroyl-?-d-glucoside)-5-(6-O-malonyl-?-d-glucoside). 3AT was a 50 kDa monomer of protein with a pI of 5.3. It catalyzed the transfer of the p-coumaric and caffeic acids from their CoA esters to the 3-glucosyl moiety of delphinidin, cyanidin and pelargonidin 3-glucoside. Anthocyanidin 3,5-diglucosides were

  5. Phenolic compounds in blackcurrant (Ribes nigrum L.) leaves relative to leaf position and harvest date.

    PubMed

    Vagiri, Michael; Conner, Sean; Stewart, Derek; Andersson, Staffan C; Verrall, Susan; Johansson, Eva; Rumpunen, Kimmo

    2015-04-01

    Blackcurrant leaves are an essential source of phenolic compounds and this study investigated their variation relative to leaf positions and harvest date. The phenolic content varied between harvest dates, although leaf position on the shoot and interactions also played an important role. The contents of quercetin-malonyl-glucoside, kaempferol-malonyl-glucoside isomer and kaempferol-malonyl-glucoside were higher than that of the other identified phenolic compounds, whereas epigallocatechin was the lowest for all investigated leaf positions and harvest dates. The content of several of the compounds was highest in June, while quercetin-glucoside, kaempferol-glucoside and total phenols, increased towards the end of the season. Leaf position influenced the content of myricetin-malonyl-glucoside, myricetin-malonyl-glucoside isomer, quercetin-malonyl-glucoside and kaempferol-glucoside at the end of the season. Knowledge relating to the influence of ontogenetic and harvest time on the content of specific phenolic compounds might contribute in tailoring functional foods or pharmaceutical products using blackcurrant leaves as natural ingredients. PMID:25442534

  6. Systematic and Applied Microbiology 28 (2005) 749754 Mycosporines in carotenogenic yeasts

    E-print Network

    Sommaruga, Ruben

    2005-01-01

    ; Mycosporines; Mycosporine-glutaminol-glucoside; Photoprotective compounds; Systematics; Yeasts Introduction) is a well-known strategy for photoprotection in many organisms [14]. Mycosporines, are water soluble UV

  7. Montamine, a unique dimeric indole alkaloid, from the seeds of  Centaurea montana (Asteraceae), and its in vitro cytotoxic activity against the CaCo2 colon cancer cells

    Microsoft Academic Search

    Mohammad Shoeb; Stephen M. MacManus; Marcel Jaspars; Jioji Trevidu; Lutfun Nahar; Paul Kong-Thoo-Lin; Satyajit D. Sarker

    2006-01-01

    Reversed-phase HPLC analysis of the methanol extract of the seeds of Centaurea montana afforded a flavanone, montanoside (4), six epoxylignans, berchemol (7), berchemol 4?-O-?-d-glucoside (5), pinoresinol (10), pinoresinol 4-O-?-d-glucoside (8), pinoresinol 4,4?-di-O-?-d-glucoside (6), pinoresinol 4-O-apiose-(1?2)-?-d-glucoside (9), two quinic acid derivatives, trans-3-O-p-coumaroylquinic acid (1), cis-3-O-p-coumaroylquinic acid (2), and eight indole alkaloids, tryptamine (3), N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (11), cis-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (12), centcyamine (16), cis-centcyamine (17),

  8. Rehmannia glutinosa: Review of botany, chemistry and pharmacology

    Microsoft Academic Search

    Ru-Xue Zhang; Mao-Xing Li; Zheng-Ping Jia

    2008-01-01

    Rehmannia glutinosa, a widely used traditional Chinese herb, belongs to the family of Scrophulariaceae, and is taken to nourish Yin and invigorate the kidney in traditional Chinese medicine (TCM) and has a very high medicinal value. In recent decades, a great number of chemical and pharmacological studies have been done on Rehmannia glutinosa. More than 70 compounds including iridoids, saccharides,

  9. Chemical composition of essential oils from Galeopsis bifida and Phlomoides tuberosa

    Microsoft Academic Search

    D. N. Olennikov; L. V. Dudareva; L. M. Tankhaeva

    2010-01-01

    Galeopsis bifida (Lamiaceae) and Phlomoides tuberosa (Lamiaceae) are broadly distributed over steppe and foreststeppe regions of the Selenga River basin [1]. Lamas in Buryatiya used G. bifida and P. tuberosa to treat diseases of the eyes and lungs and as sedative and antidiarrhea agents [2]. Chemical investigations found in G. bifida herb flavonoids, phenylpropanoids, iridoids, triterpenes, and lipids [3–5]; in

  10. Potential application for genipin-modified gelatin in leather processing

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin is an iridoid compound extracted from gardenia fruits. Because of its low cytotoxicity, genipin can be used to replace both glutaraldehyde and formaldehyde as a crosslinking reagent. In recent years, research into the utilization of genipin for the modification of gelatin, particularly in ...

  11. Potential application for genipin-modified gelatin in leather processing

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin is a non-toxic iridoid compound, extracted from the gardenia fruits, and, because of its low cytoxicity, is replacing both glutaraldehyde and formaldehyde as a crosslinking reagent. In prior research we had shown the potential of chemical (glutaraldehyde) and enzyme (transglutaminase) modif...

  12. EFFECT OF GENIPIN ON THE THERMAL STABILITY OF HIDE POWDER

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin, derived from the iridoid glycoside geniposide isolated from the fruit of Gardenia jasminoides Ellis, is a naturally occurring protein crosslinking agent. Genipin, which is not cytotoxic, is beginning to replace glutaraldehyde as a fixative for biological tissues. This study was undertaken...

  13. CHEMICAL AND PHYSICAL EVALUATION OF THE CROSSLINKING OF BOVINE HIDE COLLAGEN BY GENIPIN

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin, a derivative of the iridoid glycoside geniposide in the fruit of Gardenia jasmindides Ellis, is a naturally occurring protein crosslinking agent, which is beginning to replace glutaraldehyde as a fixative for biological tissues. In this study the potential of genipin, alone or in combinati...

  14. 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.

  15. Black rice anthocyanins inhibit cancer cells invasion via repressions of MMPs and u-PA expression

    Microsoft Academic Search

    Pei-Ni Chen; Wu-Hsien Kuo; Chui-Liang Chiang; Hui-Ling Chiou; Yih-Shou Hsieh; Shu-Chen Chu

    2006-01-01

    Tumor metastasis is the most important cause of cancer death and various treatment strategies have targeted on preventing the occurrence of metastasis. Anthocyanins are natural colorants belonging to the flavonoid family, and are wildly used for their antioxidant properties. Here, we provided molecular evidence associated with the anti-metastatic effects of peonidin 3-glucoside and cyanidin 3-glucoside, major anthocyanins extracted from black

  16. Glycosylation of artepillin C with cultured plant cells of Phytolacca americana.

    PubMed

    Shimoda, Kei; Kubota, Naoji; Uesugi, Daisuke; Hamadab, Hiroki

    2014-05-01

    Biotransformation of artepillin C was investigated using cultured plant cells as biocatalysts. Artepillin C was converted into its 4- and 9-beta-D-glucosides, and 4,9-beta-D-diglucoside by cultured cells of Phytolacca americana. In contrast, cultured lpomoea batatas cells glucosylated artepillin C to only its 4- and 9-beta-D-glucosides. PMID:25026721

  17. Quercetin from Shallots (Allium cepa L. var. aggregatum) Is More Bioavailable Than

    Microsoft Academic Search

    Wieslaw Wiczkowski; Jerzy Romaszko; Adam Bucinski; Dorota Szawara-Nowak; Joanna Honke; Henryk Zielinski; Mariusz K. Piskula

    The lipophilic character of quercetin suggests that it can cross enterocyte membranes via simple diffusion. Therefore, it should be more bioavailable than its glucosides, which require preliminary hydrolysis or active transport for absorption. However, the published human studies show that quercetin is less bioavailable than its glucosides. Assuming that low bioavailabilityofquercetinaglyconeprovidedtohumansasapuresubstanceistheresultofitslowsolubilityinthedigestive tract,westudieditsbioavailabilityfromdietarysourcesinwhichquercetinwasdispersedinthefoodmatrix.Inarandomized crossover study, 9 volunteers took a single dose

  18. Indirect Homologous Competitive Enzyme-Linked Immunosorbent Assay for the Detection of a Class of Glycosylated Dihydrochalcones

    E-print Network

    Hammock, Bruce D.

    of Glycosylated Dihydrochalcones Anupama Ranganathan, Grace A. Paradise, Chad A. Hansen, Mark R. McCoy, Shirley J, California 95445, United States *S Supporting Information ABSTRACT: Hesperetin dihydrochalcone 4-glucoside, 1, and phloretin 4-glucoside, 2, belong to a family of dihydrochalcone glycosides that exhibit flavorant properties

  19. Fast and efficient separation of cytokinins from auxin and abscisic acid and their purification using mixed-mode solid-phase extraction

    Microsoft Academic Search

    Petre Ivanov Dobrev; Miroslav Kam??nek

    2002-01-01

    A method for separation of cytokinins from auxin and abscisic acid, which allows further separation of cytokinin ribotides from cytokinin bases, ribosides and glucosides and their purification on a single Oasis MCX column was developed. Due to the mixed reversed-phase and cation-exchange mode of the Oasis MCX sorbent the cationic cytokinin bases, ribosides and glucosides as well as the anionic

  20. 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

  1. Bioavailability Is Improved by Enzymatic Modification of the Citrus Flavonoid Hesperidin in Humans: A Randomized, Double-Blind, Crossover Trial1

    Microsoft Academic Search

    Inge Lise; F. Nielsen; Winnie S. S. Chee; Lea Poulsen; Elizabeth Offord-Cavin; Salka E. Rasmussen; Hanne Frederiksen; Marc Enslen; Denis Barron; Marie-Noelle Horcajada; Gary Williamson

    Hesperidin is the predominant polyphenol consumed from citrus fruits and juices. However, hesperidin is proposed to have limited bioavailability due to the rutinoside moiety attached to the flavonoid. The aim of this study was to demonstrate in human subjects that the removal of the rhamnose group to yield the corresponding flavonoid glucoside (i.e., hesperetin-7-glucoside) will improve the bioavailability of the

  2. Stability of anthocyanins from red grape skins under pressurized liquid extraction and ultrasound-assisted extraction conditions.

    PubMed

    Liazid, Ali; Barbero, Gerardo F; Azaroual, Latifa; Palma, Miguel; Barroso, Carmelo G

    2014-01-01

    The stability of anthocyanins from grape skins after applying different extraction techniques has been determined. The following compounds, previously extracted from real samples, were assessed: delphinidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, peonidin 3-glucoside, malvidin 3-glucoside, peonidin 3-acetylglucoside, malvidin 3-acetylglucoside, malvidin 3-caffeoylglucoside, petunidin 3-p-coumaroylglucoside and malvidin 3-p-coumaroylglucoside (trans). The techniques used were ultrasound-assisted extraction and pressurized liquid extraction. In ultrasound-assisted extraction, temperatures up to 75 °C can be applied without degradation of the aforementioned compounds. In pressurized liquid extraction the anthocyanins were found to be stable up to 100 °C. The relative stabilities of both the glycosidic and acylated forms were evaluated. Acylated derivatives were more stable than non-acylated forms. The differences between the two groups of compounds became more marked on working at higher temperatures and on using extraction techniques with higher levels of oxygen in the extraction media. PMID:25517342

  3. Flavonoid metabolites in the hemolymph of European pine sawfly (Neodiprion sertifer) larvae.

    PubMed

    Vihakas, Matti; Tähtinen, Petri; Ossipov, Vladimir; Salminen, Juha-Pekka

    2012-05-01

    Flavonoids in the hemolymph of European pine sawfly (Neodiprion sertifer) larvae that were feeding on Pinus sylvestris needles were identified. HPLC-ESI-MS analysis revealed that the main components in the hemolymph were flavonol di- and triglucosides and a catechin monoglucoside. These compounds were isolated from the larval hemolymph and their structures were established by HPLC-MS, GC-MS, and NMR spectroscopy. The isolated flavonoids were identified as (+)-catechin 7-O-?-glucoside, isorhamnetin 3,7,4'-tri-O-?-glucoside, kaempferol 3,7,4'-tri-O-?-glucoside, and quercetin 3,7,4'-tri-O-?-glucoside. The combined concentration of these four compounds in the hemolymph was 3.7 mg/ml. None of these compounds was present in the needles of P. sylvestris. Therefore, we propose that the flavonoid glucosides were produced by the larvae from flavonoid monoglucosides and (+)-catechin obtained from the pine needles. PMID:22527054

  4. 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

  5. Structural characterisation and antioxidant activity evaluation of phenolic compounds from cold-pressed Perilla frutescens var. arguta seed flour.

    PubMed

    Zhou, Xiao-Jing; Yan, Lin-Lin; Yin, Pei-Pei; Shi, Ling-Ling; Zhang, Jing-Hua; Liu, Yu-Jun; Ma, Chao

    2014-12-01

    A total of 11 phenolic compounds, as well as sucrose (12) and tryptophan (13), were isolated from cold-pressed Perilla frutescens var. arguta seed flour using column chromatography, and their chemical structures were identified as 3'-dehydroxyl-rosmarinic acid-3-o-glucoside (1), rosmarinic acid-3-o-glucoside (2), rosmarinic acid (3), rosmarinic acid methyl ester (4), luteolin (5), luteolin-5-o-glucoside (6), apigenin (7), caffeic acid (8), caffeic acid-3-o-glucoside (9), vanillic acid (10) and cimidahurinine (11) using NMR and time-of-flight mass spectrometry. Of these components, compound 1 is novel, and this is the first report of compounds 10 and 11 in perilla seeds. HPLC quantification combined with antioxidant activity evaluation revealed that rosmarinic acid and rosmarinic acid-3-o-glucoside were the dominant phenolic antioxidants with strong antioxidant activities. PMID:24996318

  6. Evaluation of bioactive compounds and bioactivities of soybean dried by different methods and conditions.

    PubMed

    Niamnuy, Chalida; Nachaisin, Mali; Laohavanich, Juckamas; Devahastin, Sakamon

    2011-12-01

    Soybean has attracted significant research and commercial interests due to its many health-promoting bioactive compounds, especially isoflavones (?-glucosides, malonyl-?-glucosides, acetyl-?-glucosides and aglycones). Isoflavones possess antioxidant activity and ?-glucosidase inhibitory activity, which has proved effective in the treatment of type 2 diabetes mellitus. Prior to its use, however, soybean needs to be dried to extend its storage life and to prepare the material for subsequent food or pharmaceutical processing. The present study investigated the effects of drying methods and conditions on the drying characteristics, isoflavones, antioxidant activity and ? -glucosidase inhibitory activity of dried soybean. Hot-air fluidized bed drying (HAFBD), superheated-steam fluidized bed drying (SSFBD) and gas-fired infrared combined with hot air vibrating drying (GFIR-HAVD) were carried out at various drying temperatures (50, 70, 130 and150°C). The results showed that higher drying temperatures led to higher drying rates and higher levels of ?-glucosides and antioxidant activity, but to lower levels of malonyl-?-glucosides, acetyl-?-glucosides and total isoflavones. At the same drying temperature GFIR-HAVD resulted in the highest drying rates and the highest levels of ?-glucosides, aglycones and total isoflavones, antioxidant activity as well as ?-glucosidase inhibitory activity of dried soybean. A drying temperature of 130°C gave the highest levels of aglycones and ?-glucosidase inhibitory activity in all cases. The relationships between all the studied parameters were monitored and simple correlations between them were determined. PMID:25212316

  7. Simultaneous determination of major type A and B trichothecenes, zearalenone and certain modified metabolites in Finnish cereal grains with a novel liquid chromatography-tandem mass spectrometric method.

    PubMed

    Nathanail, Alexis V; Syvähuoko, Jenna; Malachová, Alexandra; Jestoi, Marika; Varga, Elisabeth; Michlmayr, Herbert; Adam, Gerhard; Sieviläinen, Elina; Berthiller, Franz; Peltonen, Kimmo

    2015-06-01

    A reliable and sensitive liquid chromatography-tandem mass spectrometric method was developed for the simultaneous quantitative determination in cereals of the Fusarium mycotoxins HT-2 toxin, T-2 toxin, deoxynivalenol, nivalenol and zearalenone, as well as the modified metabolites 3-acetyl-deoxynivalenol, ?-zearalenol, ?-zearalenol, deoxynivalenol-3-glucoside, HT-2-3-glucoside, nivalenol-3-glucoside, zearalenone-14-glucoside, zearalenone-14-sulphate, zearalenone-16-glucoside, ?-zearalenol-14-glucoside and ?-zearalenol-14-glucoside. The 'dilute and shoot' approach was used for sample preparation after extraction with acetonitrile:water:acetic acid (79:20:1, v/v/v). Separation was carried out using reversed-phase liquid chromatography, and detection was performed using tandem mass spectrometry in the selected reaction monitoring mode. The method was in-house validated according to performance characteristics, established in Commission Regulation EC No 401/2006 and Commission Decision EC No 657/2002, prior to its application in a nationwide survey for the analysis of barley, oat and wheat samples (n?=?95) harvested in Finland during 2013. Deoxynivalenol and its glucosylated form were the most abundant of the analytes, being detected in 93 and 81 % of the samples, respectively. Concentrations of deoxynivalenol were unusually high in 2013, especially in oats, with some cases exceeding the maximum legislative limits for unprocessed oats placed on the market for first-stage processing. All modified mycotoxins analysed were detected, and the natural occurrence of some of these compounds (e.g. zearalenone-16-glucoside and nivalenol-3-glucoside) in barley, oats and/or wheat was documented for the first time. PMID:25935671

  8. Characterization and quantification of anthocyanins in selected artichoke ( Cynara scolymus L.) cultivars by HPLC–DAD–ESI–MS n

    Microsoft Academic Search

    Katrin Schütz; Markus Persike; Reinhold Carle; Andreas Schieber

    2006-01-01

    The anthocyanin pattern of artichoke heads (Cynara scolymus L.) has been investigated by high-performance liquid chromatography–electrospray ionization mass spectrometry. For this purpose a suitable extraction and liquid chromatographic method was developed. Besides the main anthocyanins—cyanidin 3,5-diglucoside, cyanidin 3-glucoside, cyanidin 3,5-malonyldiglucoside, cyanidin 3-(3??-malonyl)glucoside, and cyanidin 3-(6??-malonyl)glucoside—several minor compounds were identified. Among these, two peonidin derivatives and one delphinidin derivative were characterized

  9. Evolution of juice anthocyanins during ripening of new selected pomegranate (Punica granatum) clones

    Microsoft Academic Search

    F. Hernández; P. Melgarejo; F. A. Tomás-Barberán; F. Artés

    1999-01-01

    For five new clones of pomegranate, cultivated under homogeneous conditions, changes in juice anthocyanin contents during\\u000a ripening were studied. Six anthocyanin pigments were found to be responsible for the red color of pomegranate juice. These\\u000a were quantitatively and qualitatively analyzed by high-performance liquid chromatography and identified as delphinidin 3-glucoside\\u000a and 3,5-diglucoside, cyanidin 3-glucoside and 3,5-diglucoside and pelargonidin 3-glucoside and 3,5-diglucoside.

  10. Flavonoids from black chokeberries, Aronia melanocarpa

    Microsoft Academic Search

    Rune Slimestad; Kjell Torskangerpoll; Haavard S. Nateland; Tina Johannessen; Nils H. Giske

    2005-01-01

    Black chokeberry, Aronia melanocarpa (Michx.) Elliott (Rosaceae), was investigated for its flavonoid content. The flavanone eriodictyol 7-O-?-glucuronide (1) together with the quercetin derivatives 3-O-(6?-O-?-arabinosyl-?-glucoside) (2), 3-O-(6?-?-rhamnosyl-?-galactoside) (3), 3-O-(6?-?-rhamnosyl-?-glucoside) (4), 3-O-?-galactoside (5) and 3-O-?-glucoside (6), were detected in the fruits and flower umbels. The rare compounds 1–3 were isolated and structurally elucidated by use of 1D- and 2D-nuclear magnetic resonance experiments

  11. Effect of isoorientin isolated from Arum palaestinum on uterine smooth muscle of rats and guinea pigs.

    PubMed

    Afifi, F U; Khalil, E; Abdalla, S

    1999-05-01

    The phytochemical investigation of Arum palaestinum resulted in the isolation of two flavone C-glucosides, namely isoorientin (luteolin 6-C-glucoside) and vitexin (apigenin 8-C glucoside). The effects of isoorientin on rat isolated aorta, ileum, trachea and uterus and on guinea-pig uterus were studied. Isoorientin (10(-7)M-6 x 10(-4)M) caused concentration-dependent inhibition of the amplitude and the frequency of the phasic contractions of the rat and guinea-pig uterus but did not affect the isolated aorta, ileum or trachea. The results were discussed in relation to the effects of its aglycone luteolin reported in the literature. PMID:10465658

  12. Benzophenone glycosides from Gnidia involucrata

    Microsoft Academic Search

    Julien Ferrari; Christian Terreaux; Sevsen Sahpaz; Jerome D. Msonthi; Jean-Luc Wolfender; Kurt Hostettmann

    2000-01-01

    Six compounds have been isolated from the methanol extract of the aerial parts of Gnidia involucrata (Thymelaeaceae). They were identified as 2,3,4?,5,6-pentahydroxybenzophenone-4-C-glucoside and 2,4?,6-trihydroxy-4-methoxybenzophenone-2-O-glucoside, together with mangiferin, kaempferol-3-O-glucoside, yuankanin and manniflavanone by chemical and spectroscopic means. The structures of three additional C-glycosyl flavones — vitexin, isovitexin and isoorientin — were determined on-line by LC\\/UV\\/APCI-MSn analysis of the crude extract.

  13. Preparative Isolation and Purification of Flavonoids and Protocatechuic Acid from Sea Buckthorn Juice Concentrate ( Hippophaë rhamnoides L. ssp . rhamnoides ) by High-Speed Counter-Current Chromatography

    Microsoft Academic Search

    D. Gutzeit; V. Wray; P. Winterhalter; G. Jerz

    2007-01-01

    High-speed counter-current chromatography (HSCCC)—a support free all liquid–liquid chromatography technique—has been successfully\\u000a used for the preparative isolation of isorhamnetin 3-O-?-d-glucoside, isorhamnetin 3-O-?-rutinoside, quercetin 3-O-?-d-glucoside, syringetin 3-O-?-d-glucoside and protocatechuic acid from sea buckthorn juice concentrate (Hippophaë rhamnoides L. ssp. rhamnoides, Elaeagnaceae). The preparative HSCCC instrument was a multilayer coil planet centrifuge equipped with three preparative coils. Separation\\u000a was performed with a

  14. Isolation of chemical constituents from the aerial parts of Verbascum thapsus and their antiangiogenic and antiproliferative activities

    Microsoft Academic Search

    Yan-Li Zhao; Si-Feng Wang; Yang Li; Qiu-Xia He; Ke-Chun Liu; Yong-Ping Yang; Xiao-Li Li

    2011-01-01

    Phytochemical investigation of Verbascum thapsus led to the isolation and identification of one new iridoid compound named verbathasin A, along with ten known compounds.\\u000a The structure and relative stereochemistry of verbathasin A were elucidated by analysis of spectroscopic data. All the isolates\\u000a except 10-deoxyeucommiol and ajugol were tested for antiangiogenic and antiproliferative activities, and compounds luteolin\\u000a and 3-O-fucopyranosylsaikogenin F showed

  15. Effects of ?-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX2) in vitro

    Microsoft Academic Search

    Liuqiang Zhang; Li Feng; Qi Jia; Jinwen Xu; Rui Wang; Zhengtao Wang; Yingchun Wu; Yiming Li

    2011-01-01

    Harpagide (1) and harpagoside (2) are two iridoid glycosides existing in many medicinal plants. Although they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy of these plants, the mechanisms of their anti-inflammatory activities remain unclear. The results of our present study showed that 1 and 2 had no effects on inhibitions of cyclooxygenase (COX)-1\\/2 enzyme

  16. Chemical constituents of Barleria prionitis and their enzyme inhibitory and free radical scavenging activities

    Microsoft Academic Search

    Athar Ata; Kosmulalage S. Kalhari; Radhika Samarasekera

    2009-01-01

    From the aerial parts of Barleria prionitis, one new phenylethanoid glycoside, barlerinoside (1) along with six known iridoid glycosides, shanzhiside methyl ester (2), 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (3), barlerin (4), acetylbarlerin (5), 7-methoxydiderroside (6), and lupulinoside (7) were isolated. Structures of these compounds were elucidated with the aid of extensive NMR spectral studies and chemical reactions. Compound 1 was significantly active

  17. Discrimination of Oribotritia species by oil gland chemistry (Acari, Oribatida)

    Microsoft Academic Search

    Günther Raspotnig; Verena Leutgeb; Günther Krisper; Hans-Jörg Leis

    2011-01-01

    The chemical composition of secretions from opisthonotal (oil) glands in four species of the oribatid mite genus Oribotritia (Mixonomata, Euphthiracaroidea, Oribotritiidae) was compared by means of gas chromatography—mass spectrometry. The secretions\\u000a of all, O. banksi (from North America) and three Austrian oribotritiids (O. berlesei, O. hermanni, O. storkani), are shown to be based on certain unusual compounds, the iridoid monoterpenes

  18. Chemical composition and pharmacological properties of plants of the genus Stachys

    Microsoft Academic Search

    V. G. Kartsev; N. N. Stepanichenko; S. A. Auelbekov

    1994-01-01

    This review gives information of the distribution of alkaloids, carbohydrates, lipids, essential oils, diterpenoids, iridoids,\\u000a flavonoids, and pigments in plants of the genusStachys L. (fam. Lamiaceae). It has been shown that the genusStachys is of interest for researchers as a source of biologically active substances of various classes which are responsible for\\u000a the broad spectrum of pharmaceutical-therapeutic action of plants

  19. Chemotaxonomy and evolution of Plantago L

    Microsoft Academic Search

    N. Rønsted; H. Franzyk; P. Mølgaard; J. W. Jaroszewski; S. R. Jensen

    2003-01-01

    In continuation of our investigations of the genus Plantago L. (Plantaginaceae), sixteen species were investigated with respect to water-soluble glycosides. The iridoids auroside, strictoloside and globularicisin, as well as poliumoside, 3-[(4-ß-D-glucopyranosyloxy)phenyl]propionic acid and 2-[4-(ß-D-glucopyranosyloxy)phenyl]acetic acid were isolated from Plantago for the first time. The latter compound has not previously been isolated as a natural product. Sorbitol was the main carbohydrate

  20. Covalent anthocyanin–flavonol complexes from flowers of chive, Allium schoenoprasum

    Microsoft Academic Search

    Torgils Fossen; Rune Slimestad; Dag Olav Øvstedal; Øyvind M Andersen

    2000-01-01

    The structures of eight anthocyanins have been determined in acidified methanolic extract of pale-purple flowers of chive, Allium schoenoprasum. Four of them have been identified as the anthocyanin–flavonol complexes (cyanidin 3-O-?-glucosideAII) (kaempferol 3-O-(2-O-?-glucosylFIII-?-glucosideFII)-7-O-?-glucosiduronic acidFIV) malonateAIII (AII-6?AIII-1, FIV-2?AIII-3), 1, (cyanidin 3-O-(3-O-acetyl-?-glucosideAII) (kaempferol 3-O-(2-O-?-glucosylFIII-?-glucosideFII)-7-O-?-glucosiduronic acidFIV) malonateAIII (AII-6?AIII-1, FIV-2?AIII-3), 2, and their 7-O-(methyl-O-?-glucosiduronateFIV) analogous, 3 and 4. Pigments 1 and 2 are the

  1. Microbial Transformation of Quercetin by Bacillus cereus

    PubMed Central

    Rao, Koppaka V.; Weisner, Nghe T.

    1981-01-01

    Biotransformation of quercetin was examined with a number of bacterial cultures. In the presence of a bacterial culture (Bacillus cereus), quercetin was transformed into two crystalline products, identified as protocatechuic acid and quercetin-3-glucoside (isoquercitrin). PMID:16345844

  2. Determination of 15 isoflavone isomers in soy foods and supplements by high-performance liquid chromatography.

    PubMed

    Yanaka, Kaoru; Takebayashi, Jun; Matsumoto, Teruki; Ishimi, Yoshiko

    2012-04-25

    Soy isoflavone is the generic name for the isoflavones found in soy. We determined the concentrations of 15 soy isoflavone species, including 3 succinyl glucosides, in 22 soy foods and isoflavone supplements by high-performance liquid chromatography (HPLC). The total isoflavone contents in 14 soy foods and 8 supplements ranged from 45 to 735 ?g/g and from 1,304 to 90,224 ?g/g, respectively. Higher amounts of succinyl glucosides were detected in natto, a typical fermented soy product in Japan; these ranged from 30 to 80 ?g/g and comprised 4.1-10.9% of the total isoflavone content. In soy powder, 59 ?g/g of succinyl glucosides were detected, equivalent to 4.6% of the total isoflavone content. These data suggest that the total isoflavone contents may be underestimated in the previous studies that have not included succinyl glucosides, especially for Bacillus subtilis -fermented soy food products. PMID:22433078

  3. Flavonoids from Achillea nobilis L.

    PubMed

    Krenn, Liselotte; Miron, Anca; Pemp, Enne; Petr, Ursula; Kopp, Brigitte

    2003-01-01

    The detailed investigation of a methanolic extract of aerial parts of Achillea nobilis resulted in the isolation of 10 flavonoids. A new C-glycosylflavone, luteolin-6-C-apiofuranosyl-(1'''-->2'')-glucoside, was isolated besides orientin, isoorientin, vitexin, isoschaftoside, luteolin-7-O-beta-glucuronide, luteolin-4'-O-beta-glucoside and quercetin-3-O-methyl ether and two rare flavonolglycosides, quercetin-3-O-alpha-arabinosyl-(1'''-->6'')-glucoside and quercetin-3-O-methylether-7-O-beta-glucoside. The structures were established either by comparison with authentic substances or by UV, 1H NMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS. PMID:12622219

  4. Characterization and quantification of anthocyanins and polyphenolics in bluehHoneysuckle (Lonicera caerulea L.).

    PubMed

    Chaovanalikit, Arusa; Thompson, Maxine M; Wrolstad, Ronald E

    2004-02-25

    Anthocyanins and phenolics of 10 blue honeysuckle (Lonicera caerulea L.) genotypes were characterized and quantified by HPLC-DAD. Peak assignments were confirmed by low-resolution electrospray mass spectrometry. Six anthocyanins were detected with the major peak identified as cyanidin 3-glucoside. Five additional anthocyanins were characterized as cyanidin 3,5-diglucoside, cyanidin 3-rutinoside, pelargonidin 3-glucoside, peonidin 3-glucoside, and peonidin 3-rutinoside. Four polyphenolics were identified as chlorogenic acid, neochlorogenic acid, quercetin 3-rutinoside, and quercetin 3-glucoside. Two additional unidentified phenolics were characterized as flavonol and hydroxycinnamic derivatives based on UV-vis spectra. Hydroxycinnamate levels ranged from 30.4 to 156.2 mg/100 g, whereas the flavonol content ranged from 12.6 to 32.8 mg/100 g. The L. caerulea subspecies boczkarnikovae contained the highest amounts of hydroxycinnamic derivatives and flavonols. PMID:14969540

  5. PHYTOCHEMICAL CONTENT IN BLUEBERRIES IS INFLUENCED BY UV ILLUMINATION

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The levels of phytochemicals in blueberries were found to increase after illumination with UV-C light. Phytochemicals affected included resveratrol, myricetin 3-arabinoside, quercetin 3-galactoside, quercetin 3-arabinoside, quercetin derivative, kaempferol 3-glucoside, delphinidin-3-galactoside, cy...

  6. 7,3?-Dihydroxy-4?-Methoxyflavone from seeds of acacia farnesiana

    Microsoft Academic Search

    Niranjan P Sahu; Basudeb Achari; Sukdeb Banerjee

    1998-01-01

    Besides the known flavone diosmetin and sitosterol glucoside, a new flavone farnisin has been isolated from the seeds of Acacia farnesiana. Its structure was established as 7,3?-dihydroxy-4?-methoxyflavone from spectroscopic studies and chemical transformation.

  7. Development of a Chemically Defined Medium to Assay the Metabolism of Lactic Acid Bacteria

    E-print Network

    Kim, Inhye

    2014-04-16

    to identify LAB with specific enzyme activities of interest, specifically ?-glycoside hydrolase activity. In this model system, LAB were screened for their capacity to catabolize genistin (Gin^(+)), a glucoside (glycone) of genistein (genistein 7-O...

  8. J. Biomater. Sci. Polymer Edn, Vol. 13, No. 11, pp. 12711281 (2002) VSP 2002.

    E-print Network

    Peppas, Nicholas A.

    2002-01-01

    - methacryloxyethyl glucoside, using tetra(ethylene glycol) dimethacrylate as a cross-linking agent. To determine protein delivery carriers. Glycopolymers are synthetic polymers containing pendent mono-, oligo-, or poly

  9. [Triterpenes and steroids in callus cultures of Solanum dulcamara].

    PubMed

    Willuhn, G; May, S

    1982-11-01

    From tissue cultures (callus) of the soladulcidine strain of Solanum dulcamara L. the 4,4-dimethylsterols cycloartenol, cycloartanol, 24-dihydrolanosterol, and 24-methylenecycloartanol and the sterols cholesterol, 24-methylenecholesterol, campesterol, stigmasterol, isofucosterol, and sitosterol were identified by GC and GC/MS. In the callus the sterols are present in the free form and as esters, glucosides and palmitic esters of the glucosides. The total contents and the contents of the combined forms were determined photometrically (total: 0.19% on dry weight basis, 59.4% glucosides and acylated glucosides, 4.7% esters, 35.9% free). The main fatty acids of the petrolether soluble lipids of the callus (1.78%) are palmitic-, linoleic-, and linolenic acid. PMID:17396963

  10. Theory and phenomenology of mixed amphiphilic aggregates Michael M Kozlov* and David Andelman!

    E-print Network

    Andelman, David

    362 Theory and phenomenology of mixed amphiphilic aggregates Michael M Kozlov* and David Andelman! There has been much experimental data and theory in relation to amphiphilic aggregates presented recently dioleoylphosphatidylcholine DOPE dioleoylphosphatidylethanolamine OG octyl glucoside Introduction An amphiphilic molecule

  11. Transformation of the host-selective toxin destruxin B by wild crucifers: probing a detoxification pathway

    Microsoft Academic Search

    M. S. C. Pedras; S. Montaut; I. L. Zaharia; Y. Gai; D. E. Ward

    2003-01-01

    Destruxin B is detoxified to the malonylated glucoside in Camelina sativa, Capsella bursa-pastoris, and Eruca sativa, suggesting a conservation of this detoxification pathway in both wild and cultivated crucifers.

  12. ANTHOCYANINS (ACNS) WERE ABSORBED AND METABOLIZED DIFFERENTLY IN WEANLING PIGS AFTER FEEDING BLACK CURRANT (BC) OR CHOKEBERRY (CB)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Metabolism of ACNs in vivo was studied in weanling pigs fed BC (3.0g/kg BW; n=8) or CB (2.0 g/kg BW; n=6). There were 4 major ACNs in BC (delphinidin-3-glucoside, Dp-3Gle; delphinidin-3-rutinoside, Cy-3R; Cyanidin-3-glucoside, Cy-3Gle and cyanidin-3-rutinoside, Cy-3R) and four in CB (cyanidin-3-gal...

  13. Phase change modifies anthocyanin synthesis in Acer palmatum Thunb. (Japanese maple) cultivars

    Microsoft Academic Search

    Valentina Schmitzer; Franci Stampar; Robert Veberic; Gregor Osterc

    2009-01-01

    The potential markers of juvenility (cyanidin 3-glucoside and cyanidin 3-rutinoside) in autumn leaves of seven Acer palmatum Thunb. cultivars were investigated. Three shoot positions were marked on each cultivar—crown shoot, middle shoot, and basal\\u000a shoot—and the anthocyanins were analyzed using HPLC-MS. The results showed great differences in cyanidin 3-glucoside and cyanidin\\u000a 3-rutinoside concentrations among seven cultivars; moreover, significant differences in

  14. Flavonols: Pigments Responsible for Ultraviolet Absorption in Nectar Guide of Flower

    Microsoft Academic Search

    W. R. Thompson; Jerrold Meinwald; D. Aneshansley; Thomas Eisner

    1972-01-01

    The petals of the black-eyed susan (Compositae: Rudbeckia hirta) contain three flavonol glucosides (6,7-dimethoxy-3',4',5-trihydroxyflavone-3-O- glucoside, patulitrin, and quercetagetin). These compounds, which show intense spectral absorption at 340 to 380 nanometers, are restricted in distribution to the petal bases, which are ultraviolet absorbing as a result. Such ultraviolet-absorbing petal zones, known as \\

  15. Isolierung und Identifizierung der Flavon(ol)-O-glykoside in Kümmel (Carum carvi L.), Fenchel (Foeniculum vulgare Mill.), Anis (Pimpinella anisum L.) und Koriander (Coriandrum sativum L.) und von Flavon-C-glykosiden im Anis

    Microsoft Academic Search

    Jost Kunzemann; Karl Herrmann

    1977-01-01

    Summary The flavonoid constituents of various spices were separated by means of chromatography on cellulose colums, and the following compounds were obtained crystalline: Quercetin 3-glucuronide from caraway, fennel, anise, and coriander; isoquercitrin from caraway and fennel; rutin from fennel and anise; quercetin 3-O-caffeylglucoside and kaempferol 3-glucoside from caraway; quercetin 3-arabinoside from fennel, and luteolin 7-glucoside, isoorientin and isovitexin from anise.

  16. Metabolism and compartmentation of dihydrozeatin exogenously supplied to photoautotrophic suspension cultures of Chenopodium rubrum

    Microsoft Academic Search

    A. Fusseder; P. Ziegler

    1988-01-01

    [3H]Dihydrozeatin supplied to photoautotrophically growing cell suspension cultures of Chenopodium rubrum was rapidly taken up and metabolized by the cells. The predominant metabolites in extracts of the cells were [3H]dihydrozeatin-O-glucoside and [3H]dihydrozeatin riboside-O-glucoside. Both these compounds could be shown to be compartmented within the vacuole, whereas [3H]dihydrozeatin and [3H]dihydrozeatin riboside, which were both present to a minor extent in cell

  17. Cardenolides from Adonis aestivalis.

    PubMed

    Kopp, B; Krenn, L; Kubelka, E; Kubelka, W

    1992-09-01

    Four cardenolides were isolated for the first time from the aerial parts of Adonis aestivalis. The compounds were identified by spectrometry and for 3-epi-periplogenin, helveticoside also by comparison with authentic substances. Two new cardenolides were structurally elucidated: strophanthidin-3-O-beta-D-digitoxosido-alpha-L-cymarosido-be ta-D-glucoside and strophanthidin-3-O-beta-D-digitoxosido-beta-D-digoxoside-bet a-D-diginosido-beta-D-glucoside. PMID:1368415

  18. 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

  19. A new flavanone from the aerial parts of Penthorum chinense.

    PubMed

    Wang, Meng; Jiang, Yun; Liu, Hao-Long; Chen, Xiao-Qing; Wu, Xia; Zhang, Da-Yong

    2014-01-01

    A new flavanone, 5-methoxy-pinocembrin-7-O-?-D-glucoside (1), together with six known compounds, quercetin-3-O-?-D-xyloside (2), quercetin-3'-O-?-L-rhamnoside (3), quercetin (4), pinocembrin-7-O-?-D-glucoside (5), pinocembrin (6), gallic acid (7), were isolated and identified from the aerial parts of Penthorum chinense. Compounds 2 and 3 were isolated from this plant for the first time. PMID:24456387

  20. Genetical and biochemical evidence that the hydroxylation pattern of the anthocyanin Bring in Silene dioica is determined at the p-coumaroyl-coenzyme a stage

    Microsoft Academic Search

    J. Kamsteeg; J. van Brederode; G. van Nigtevecht

    1980-01-01

    In petals of Silene dioica, gene P controls the 3?-hydroxylation of the anthocyanin B-ring and the hydroxylation pattern of the hydroxycinnamoyl acyl group bound to the 4?'-hydroxyl group of rhamnose of anthocyanidin 3-rhamnosyl(1?6)glucoside-5-glucoside. In this paper, experiments are presented which show that gene P is involved in the hydroxylation of p-coumaroyl-CoA to caffeoyl-CoA, which is then used both as a