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Sample records for chromone

  1. Chromones.

    Science.gov (United States)

    Edwards, Alan M

    2014-01-01

    The chromones are a class of chemical compounds characterised by the presence of the structure 5:6 benz-1:4-pyrone in their chemical make-up. The first chromone in clinical use, khellin, was extracted from the seeds of the plant Ammi visnaga, and had been used for centuries as a diuretic and as a smooth muscle relaxant. Its use in bronchial asthma was reported in 1947. In the 1950s, Benger's Laboratories embarked on a research programme to synthesise and develop modifications of khellin for the treatment of asthma. New compounds were screened using animal models to test the ability of the compound to prevent the anaphylactic release of histamine and SRS-A (leukotrienes) from sensitised guinea pig lung, and a human model to check the ability to reduce the bronchoconstriction induced by inhaled antigen bronchial challenge. For initial screening the human work was undertaken by Dr. R.E.C. Altounyan, who suffered from allergic bronchial asthma and was employed by Benger's Laboratories. After 8 years and more than 600 challenges using over 200 compounds, in 1965 Altounyan arrived at disodium cromoglycate (DSCG), the chromone that met the criteria of providing more than 6 h of protection. DSCG is still used today as a mast cell stabiliser. PMID:24925412

  2. Granulosin, a new chromone from Galipea granulosa.

    Science.gov (United States)

    Lpez, J A; Barillas, W; Gomez-Laurito, J; Martin, G E; Al-Rehaily, A J; Zemaitis, M A; Schiff, P L

    1997-01-01

    A novel chromone, granulosin (1), has been isolated from the bark of Galipea granulosa. The extract of the bark, as well as granulosin (1), exhibited lethality in the brine shrimp test. The structure of granulosin (1) as 2-propyl-7,8-(methylenedioxy)chromone was established via spectroscopic analysis. PMID:9064364

  3. Physiochemical, Optical and Biological Activity of Chitosan-Chromone Derivative for Biomedical Applications

    OpenAIRE

    Joonseok Koh; Santosh Kumar

    2012-01-01

    This paper describes the physiochemical, optical and biological activity of chitosan-chromone derivative. The chitosan-chromone derivative gels were prepared by reacting chitosan with chromone-3-carbaldehyde, followed by solvent exchange, filtration and drying by evaporation. The identity of Schiff base was confirmed by UV-Vis absorption spectroscopy and Fourier-transform infrared (FTIR) spectroscopy. The chitosan-chromone derivative was evaluated by X-ray diffraction (XRD), thermogravimetric...

  4. Glueball-Quarkonium Mixing in the Quark and Chromon Model

    CERN Document Server

    Zhang, Pengming; Xie, Ju-Jun; Yoon, J H; Cho, Y M

    2016-01-01

    The Abelian decomposition of QCD which decomposes the gluons to the color neutral binding gluons (the neurons) and the colored valence gluons (the chromons) gauge independently naturally generalizes the quark model to the quark and chromon model which can play the central role in hadron spectroscopy. We discuss how the quark and chromon model describes the glueballs and the glueball-quarkonium mixing in QCD. We present the numerical analysis of glueball-quarkonium mixing in $0^{++}$, $2^{++}$, and $0^{-+}$ sectors below 2 GeV, and show that in the $0^{++}$ sector $f_0(500)$ and $f_0(1500)$, in the $2^{++}$ sector $f_2(1950)$, and in the $0^{-+}$ sector $\\eta(1405)$ and $\\eta(1475)$ could be identified as predominantly the glueball states. We discuss the physical implications of our result.

  5. Optical characterization of lyotropic chromonic liquid crystals

    Science.gov (United States)

    Liu, Hui

    Lyotropic chromonic liquid crystals (LCLCs) represent a special class of lyotropic mesophases markedly different from conventional amphiphilic mesogens. Materials forming LCLCs are composed of plank-like molecules with a polyaromatic central core and hydrophilic ionic groups at the periphery. The individual molecules tend to assemble into rodlike aggregates that form the N phase once the concentration exceeds about 0.1M. The LCLC materials show a tremendous potential for applications in optics as self-assembling polarizing and compensating films and in the area of real-time biological sensing. The emerging applications require an understanding of basic properties of LCLC. This work addresses these needs by providing the optical characterization of LCLC. We studied in detail the optical anisotropic properties of three different nematic LCLCs: disodium cromoglycate (DSCG), Blue 27, and Violet 20. We determined the birefringence of these three materials as the function of the temperature T and wavelength lambda and the corresponding dependencies of the absorption coefficients for Blue 27 and Violet 20. The birefringence is negative and significantly lower in the absolute value as compared to the birefringence of typical thermotropic N materials. We determined the scalar order parameter of the nematic phase of Blue 27 and its temperature dependence. The scalar order parameter is close to the one predicted by the classic Onsager theory for solutions of rigid rods. However, this similarity is not complete, as the measured scalar order parameter depends on temperature. The I-N pretransitional fluctuations in an aqueous solution of DSCG were studied by light scattering. We obtained the correlation length of the orientational order-parameter fluctuations of isotropic DSCG solution. The pretransitional behavior of light scattering does not completely follow the classic Landau-de Gennes model. This feature is explained by the variable length of DSCG aggregates as a function

  6. Studies on the antioxidant activities of some new chromone compounds.

    Science.gov (United States)

    Kładna, Aleksandra; Berczyński, Paweł; Piechowska, Teresa; Kruk, Irena; Aboul-Enein, Hassan Y; Ceylan-Unlusoy, Meltem; Verspohl, Eugen J; Ertan, Rahmiye

    2014-11-01

    Recent reviews evidence that the naturally occurring compounds containing the chromone skeleton exhibit antiradical activities, providing protection against oxidative stress. The antioxidant activities of 13 new synthesized chromonyl-2,4-thiazolidinediones, chromonyl-2,4-imidazolidinediones and chromonyl-2-thioxoimidzolidine-4-ones were evaluated using in vitro antioxidant assays, including superoxide anion radical (O2(-•)), hydroxyl radical (HO(•)), 2,2-diphenyl-1-picryl-hydrazyl free radical (DPPH(•)) scavenging capacity and total antioxidant capacity ferric ion reducing activity. Superoxide anion radical was produced using potassium superoxide/18-crown-6-ether dissolved in dimethylsulfoxide, and the Fenton-like reaction (Fe(II) + H2O2) was a generator of hydroxyl radicals. Chemiluminescence, spectrophotometry, electron paramagnetic resonance (EPR) and 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as the spin trap were the measurement techniques. The results showed that the majority of the chromone derivatives tested showed a strong scavenging effect towards free radicals, similar to the chemiluminescence reaction with superoxide anion radical with a high activity, inhibition of the DMPO-OOH radical EPR signal (24-58%), the DMPO-OH radical EPR signal (4-75%) and DPPH radical EPR signal (6-100%) at 1 mmol/L. Several of the examined compounds exhibited the high reduction potentials. The results obtained show that the new synthesized chromone derivatives may directly scavenger reactive oxygen species and thus may play a protective role against oxidative damage. PMID:24482260

  7. New chromone derivative terminalianone from African plant Terminalia brownii Fresen (Combretaceae) in Tanzania.

    Science.gov (United States)

    Negishi, Hiroko; Maoka, Takashi; Njelekela, Marina; Yasui, Naomi; Juman, Sachiko; Mtabaji, Jacob; Miki, Tomohiro; Nara, Yasuo; Yamori, Yukio; Ikeda, Katsumi

    2011-03-01

    A new chromone derivative named terminalianone (1) was isolated from the African plant, Terminalia brownii Fresen (Combretaceae) in Tanzania. Its structure was determined to be 7-hydroxy-3-[6'-hydroxyphenyl-2'-oxo-ethyl]chromone by FAB-MS and NMR spectral data. PMID:21409693

  8. Ring transformation of chromone-3-carboxamide under nucleophilic conditions

    Energy Technology Data Exchange (ETDEWEB)

    Ibrahim, Magdy A., E-mail: magdy_ahmed1977@yahoo.com [Department of Chemistry, Faculty of Education, Ain Shams University, Cairo(Egypt)

    2013-11-15

    The chemical reactivity of chromone-3-carboxamide was studied towards a series of nitrogen and carbon nucleophiles. Treatment of carboxamide with some primary amines gave chromane-2,4-diones. Condensation of carboxamide with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride afforded chromenopyrazoles and chromenoisoxazole, respectively. Reaction of carboxamide with guanidine hydrochloride, cyanoguanidine and thiourea resulted in ring transformation producing chromenopyridines. The chemical behavior of carboxamide was also studied towards ethylenediamine, o-phenylenediamine, 2-aminophenol and 2-aminothiophenol. A variety of products were isolated from the reaction of carboxamide with some carbon nucleophiles. (author)

  9. Brownian Dynamics of Colloidal Particles in Lyotropic Chromonic Liquid Crystals

    Science.gov (United States)

    Martinez, Angel; Collings, Peter J.; Yodh, Arjun G.

    We employ video microscopy to study the Brownian dynamics of colloidal particles in the nematic phase of lyotropic chromonic liquid crystals (LCLCs). These LCLCs (in this case, DSCG) are water soluble, and their nematic phases are characterized by an unusually large elastic anisotropy. Our preliminary measurements of particle mean-square displacement for polystyrene colloidal particles (~5 micron-diameter) show diffusive and sub-diffusive behaviors moving parallel and perpendicular to the nematic director, respectively. In order to understand these motions, we are developing models that incorporate the relaxation of elastic distortions of the surrounding nematic field. Further experiments to confirm these preliminary results and to determine the origin of these deviations compared to simple diffusion theory are ongoing; our results will also be compared to previous diffusion experiments in nematic liquid crystals. We gratefully acknowledge financial support through NSF DMR12-05463, MRSEC DMR11-20901, and NASA NNX08AO0G.

  10. A new chromone from Hymenocallis littoralis Salisb. (Amaryllidaceae).

    Science.gov (United States)

    Anh, Dinh Thi Phuong; Duong, Tran Bach; Hoang, Vu Dinh

    2014-01-01

    A new chromone, 5,7-dihydroxy-6,8-dimethoxy-2-methyl-4H-chromen-4-one (1), together with seven known compounds, 5,7-dihydroxy-6-methoxy-2-methyl-4H-chromen-4-one (pisonin B) (2), 5,7-dihydroxy-2-methyl-4H-chromen-4-one (noreugenin) (3), 5-hydroxy-7-methoxy-2-methyl-4H-chromen-4-one (eugenin) (4), (2S)-7,4'-dihydroxyflavan (5), 3',7-dihydroxy-4'-methoxy-8-methylflavan (6), 3',7-dihydroxy-4'-methoxyflavan (7) and 6,8-dimethyl-5,7,4'-trihydroxyflavanone (( - )-farrerol) (8), were isolated from Hymenocallis littoralis Salisb. (Amaryllidaceae) growing in Vietnam. Their structures were determined based on spectroscopic and physicochemical analyses. PMID:25142217

  11. Homeotropic alignment of lyotropic chromonic liquid crystals using noncovalent interactions.

    Science.gov (United States)

    Jeong, Joonwoo; Han, Ganghee; Johnson, A T Charlie; Collings, Peter J; Lubensky, Tom C; Yodh, Arjun G

    2014-03-18

    We report on the homeotropic alignment of lyotropic chromonic liquid crystals (LCLCs). Homeotropic anchoring of LCLCs is difficult to achieve, and this challenge has limited development of applications for LCLCs. In this work, homeotropic alignment is achieved using noncovalent interactions between the LCLC molecules and various alignment layers including graphene, parylene films, poly(methyl methacrylate) films, and fluoropolymer films. The LCLC molecules are unique in that they self-assemble via noncovalent interactions in water into elongated aggregates which, in turn, form nematic and columnar liquid crystal (LC) phases. Here we exploit these same noncovalent interactions to induce homeotropic anchoring of the nematic LCLC. Homeotropic alignment is confirmed by polarized optical microscopy and conoscopy. We also report on novel transient stripe textures that occur when an initial flow-induced planar alignment transforms into the equilibrium homeotropic alignment required by boundary conditions. An understanding of this behavior could be important for switching applications. PMID:24559290

  12. Analysis of 2-(2-Phenylethyl)chromones by UPLC-ESI-QTOF-MS and Multivariate Statistical Methods in Wild and Cultivated Agarwood

    Science.gov (United States)

    Li, Yuanbin; Sheng, Nan; Wang, Lingli; Li, Shijie; Chen, Jiannan; Lai, Xiaoping

    2016-01-01

    Agarwood is the fragrant resinous material mainly formed from species of Aquilaria. 2-(2-phenylethyl)chromones, especially the highly oxidized 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones, are the main representative compounds from agarwood. It is important to determine whether agarwood in trade is from cultivated trees or natural trees in the Convention on the International Trade in Endangered Species (CITES). We characterized the 2-(2-phenylethyl)chromones in agarwood by ultra-performance liquid chromatography coupled with electrospray ionization mass spectrometry (UPLC–ESI-QTOF-MS) and differentiated wild from cultivated agarwood by metabolomic analysis. A total of 141 chromones including 50 potentially new compounds were evaluated as belonging to four structural classes (unoxidized 2-(2-phenylethyl)chromones, 5,6,7,8-tetrahydro-2-(2-phenylethyl)-chromones, bi-2-(2-phenylethyl)chromones, and tri-2-(2-phenylethyl)chromones). The metabolic difference between wild and cultivated agarwood was analyzed by component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA). Fourteen markers of metabolisms in wild and cultivated agarwood were constructed (e.g., 6,7-dimethoxy-2-(2-phenylethyl)chromone, 6,8-dihydroxy-2-(2-phenylethyl)chromone, 6-methoxy-2-(2-phenylethyl)chromone, etc.). These results indicated that UPLC–ESI-QTOF-MS-based metabonomics analysis in agarwood may be useful for distinguishing wild agarwood from cultivated agarwood. PMID:27223280

  13. Analysis of 2-(2-Phenylethyl)chromones by UPLC-ESI-QTOF-MS and Multivariate Statistical Methods in Wild and Cultivated Agarwood.

    Science.gov (United States)

    Li, Yuanbin; Sheng, Nan; Wang, Lingli; Li, Shijie; Chen, Jiannan; Lai, Xiaoping

    2016-01-01

    Agarwood is the fragrant resinous material mainly formed from species of Aquilaria. 2-(2-phenylethyl)chromones, especially the highly oxidized 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones, are the main representative compounds from agarwood. It is important to determine whether agarwood in trade is from cultivated trees or natural trees in the Convention on the International Trade in Endangered Species (CITES). We characterized the 2-(2-phenylethyl)chromones in agarwood by ultra-performance liquid chromatography coupled with electrospray ionization mass spectrometry (UPLC-ESI-QTOF-MS) and differentiated wild from cultivated agarwood by metabolomic analysis. A total of 141 chromones including 50 potentially new compounds were evaluated as belonging to four structural classes (unoxidized 2-(2-phenylethyl)chromones, 5,6,7,8-tetrahydro-2-(2-phenylethyl)-chromones, bi-2-(2-phenylethyl)chromones, and tri-2-(2-phenylethyl)chromones). The metabolic difference between wild and cultivated agarwood was analyzed by component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA). Fourteen markers of metabolisms in wild and cultivated agarwood were constructed (e.g., 6,7-dimethoxy-2-(2-phenylethyl)chromone, 6,8-dihydroxy-2-(2-phenylethyl)chromone, 6-methoxy-2-(2-phenylethyl)chromone, etc.). These results indicated that UPLC-ESI-QTOF-MS-based metabonomics analysis in agarwood may be useful for distinguishing wild agarwood from cultivated agarwood. PMID:27223280

  14. Adding Mono- and Multivalent Ions to Lyotropic Chromonic Liquid Crystals

    Science.gov (United States)

    Tortora, Luana; Park, Heung-Shik; Antion, Kelly; Woolwerton, Chris; Finotello, Daniele; Lavrentovich, Oleg

    2006-03-01

    Lyotropic Chromonic Liquid Crystals (LCLCs) are a distinct class of liquid crystals formed in aqueous solutions by molecules with rigid polyaromatic cores and ionic groups at the periphery [1-4]. The phase diagrams of these materials should depend on entropic factors (as in the Onsager model) and electrostatic interactions. Using optical polarizing microscopy, we studied the effects of mono- and multivalent ions on the phase diagrams of Blue 27 [3] and Sunset Yellow [2]. The monovalent ions change the temperatures of phase transitions, as described in [4], while the effect of multivalent ions is more dramatic and, in addition to the changed temperatures of phase transitions by tens of degrees, it often involves condensation of LCLC aggregates into domains with birefringence much higher than that in a normal nematic phase. Work supported by OBR B-7844. [1]J. Lydon, Current Opin. Colloid & Interface Sci. 3, 458 (1998);8, 480-489 (2004); [2]V. R. Horowitz, L. A. Janowitz, A. L. Modic, P. J. Heiney, and P. J. Collings, 2005, Phys. Rew. E 72, 041710; [3]Yu. A. Nastishin, H. Liu, T. Schneider, T., V. Nazarenko, R. Vasyuta, S. V. Shiyanovskii, and O. D. Lavrentovich, 2005, Phys. Rev. E 72, 041711; [4]A.F. Kostko, B. H. Cipriano, O. A. Pinchuk, L. Ziserman, M. A. Anisimov, D. Danino, and S. R. Raghavan. J. Phys. Chem. B 109, 19126-19133 (2005)

  15. Preussianone, a New Flavanone-Chromone Biflavonoid from Garcinia preussii Engl.

    OpenAIRE

    Gerhard Bringmann; Kurt Hostettmann; Jean-Luc Wolfender; Alain Meli Lannang; Nkengfack, Augustin E; Barbara Hertlein-Amslinger; Karine Ndjoko-Ioset; Bernadette Biloa Messi

    2012-01-01

    A new flavanone-chromone biflavonoid, preussianone (1), has been isolated from the leaves of Garcinia preussii, along with four known biflavonoids. The absolute stereostructures were elucidated by chemical, spectroscopic, and chiroptical methods. The biological properties of the new biflavonoid against several bacterial strains were evaluated.

  16. Divergent reactivity of homologue ortho-allenylbenzaldehydes controlled by the tether length: chromone versus chromene formation.

    Science.gov (United States)

    Alcaide, Benito; Almendros, Pedro; Fernández, Israel; Martínez del Campo, Teresa; Naranjo, Teresa

    2015-01-19

    The divergent behavior of two homologue allenals, namely, 2-(buta-2,3-dienyloxy)- and 2-(propa-1,2-dienyloxy)benzaldehydes, as cyclization substrates is described. 2-(Buta-2,3-dienyloxy)benzaldehydes suffers a formal allenic carbocyclization reaction to afford chromenes, whereas 2-(propa-1,2-dienyloxy)benzaldehydes react to yield chromones. The formation of chromenes is strictly a formal hydroarylation process divided into two parts, namely, allenic Claisen-type rearrangement and oxycyclization. An unknown N-heterocyclic carbene (NHC)-catalyzed allenic hydroacylation reaction must be invoked to account for the preparation of chromones. ortho-Allenylbenzaldehydes bearing either electron-donating substituents or electron-withdrawing substituents worked well to afford both the hydroarylation and hydroacylation products. This unexpected difference in reactivity can be rationalized by means of density functional theory calculations. PMID:25418081

  17. Alignment and Graphene-Assisted Decoration of Lyotropic Chromonic Liquid Crystals Containing DNA Origami Nanostructures.

    Science.gov (United States)

    Martens, Kevin; Funck, Timon; Kempter, Susanne; Roller, Eva-Maria; Liedl, Tim; Blaschke, Benno M; Knecht, Peter; Garrido, José Antonio; Zhang, Bingru; Kitzerow, Heinz

    2016-03-01

    Composites of DNA origami nanostructures dispersed in a lyotropic chromonic liquid crystal are studied by polarizing optical microscopy. The homogeneous aqueous dispersions can be uniformly aligned by confinement between two glass substrates, either parallel to the substrates owing to uniaxial rubbing or perpendicular to the substrates using ozonized graphene layers. These opportunities of uniform alignment may pave the way for tailored anisometric plasmonic DNA nanostructures to photonic materials. In addition, a decorated texture with nonuniform orientation is observed on substrates coated with pristine graphene. When the water is allowed to evaporate slowly, microscopic crystal needles appear, which are aligned along the local orientation of the director. This decoration method can be used for studying the local orientational order and the defects in chromonic liquid crystals. PMID:26849188

  18. Cobalt-Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4-Chromanones.

    Science.gov (United States)

    Yang, Junfeng; Yoshikai, Naohiko

    2016-02-01

    A unique cobalt(I)-diphosphine catalytic system has been identified for the coupling of salicylaldehyde (SA) and an internal alkyne affording a dehydrogenative annulation product (chromone) or a reductive annulation product (4-chromanone) depending on the alkyne substituents. Distinct from related rhodium(I)- and rhodium(III)-catalyzed reactions of SA and alkynes, these annulation reactions feature aldehyde C-H oxidative addition of SA and subsequent hydrometalation of the C=O bond of another SA molecule as common key steps. The reductive annulation to 4-chromanones also involves the action of Zn as a stoichiometric reductant. In addition to these mechanistic features, the Co(I) catalysis described herein is complementary to the Rh(I) - and Rh(III) -catalyzed reactions of SA and internal alkynes, particularly in the context of chromone synthesis. PMID:26804050

  19. Flavanones and Chromones from Salicornia herbacea Mitigate Septic Lethality via Restoration of Vascular Barrier Integrity.

    Science.gov (United States)

    Tuan, Nguyen Quoc; Lee, Wonhwa; Oh, Joonseok; Kulkarni, Roshan Rajan; Gény, Charlotte; Jung, Byeongjin; Kang, Hyejin; Bae, Jong-Sup; Na, MinKyun

    2015-11-25

    Salicornia herbacea is an annual halophytic glasswort that has been employed as a culinary vegetable, salad, and traditional medicinal resource. Chemical investigation of the aerial parts of S. herbacea led to the isolation of two new (1, 2) and known (3) flavanones as well as a new nature-derived (4) and two known chromone derivatives (5, 6). These purified compounds were evaluated for their suppressive potentials against the release of high-mobility group box 1 protein (HMGB1), which has captured attention as a viable target for alleviating serious septic manifestations or septicemia. The phenolic compounds improved the survival rates of cecal ligation and puncture operation (CLP) in murine models, simulating severe septic shock and its related complications, to 40-60%. These results collectively validate that flavanone- and chromone-based secondary metabolites may serve as prospective prodrugs or food additives that may be commercialized for the control of septic complications and lethality. PMID:26522440

  20. Spontaneous emergence of chirality in achiral lyotropic chromonic liquid crystals confined to cylinders.

    Science.gov (United States)

    Nayani, Karthik; Chang, Rui; Fu, Jinxin; Ellis, Perry W; Fernandez-Nieves, Alberto; Park, Jung Ok; Srinivasarao, Mohan

    2015-01-01

    The presumed ground state of a nematic fluid confined in a cylindrical geometry with planar anchoring corresponds to that of an axial configuration, wherein the director, free of deformations, is along the long axis of the cylinder. However, upon confinement of lyotropic chromonic liquid crystals in cylindrical geometries, here we uncover a surprising ground state corresponding to a doubly twisted director configuration. The stability of this ground state, which involves significant director deformations, can be rationalized by the saddle-splay contribution to the free energy. We show that sufficient anisotropy in the elastic constants drives the transition from a deformation-free ground state to a doubly twisted structure, and results in spontaneous symmetry breaking with equal probability for either handedness. Enabled by the twist angle measurements of the spontaneous twist, we determine the saddle-splay elastic constant for chromonic liquid crystals for the first time. PMID:26287517

  1. 3D-QSAR Investigation of Synthetic Antioxidant Chromone Derivatives by Molecular Field Analysis

    Directory of Open Access Journals (Sweden)

    Jiraporn Ungwitayatorn

    2008-02-01

    Full Text Available A series of 7-hydroxy, 8-hydroxy and 7,8-dihydroxy synthetic chromone derivatives was evaluated for their DPPH free radical scavenging activities. A training set of 30 synthetic chromone derivatives was subject to three-dimensional quantitative structure-activity relationship (3D-QSAR studies using molecular field analysis (MFA. The substitutional requirements for favorable antioxidant activity were investigated and a predictive model that could be used for the design of novel antioxidants was derived. Regression analysis was carried out using genetic partial least squares (G/PLS method. A highly predictive and statistically significant model was generated. The predictive ability of the developed model was assessed using a test set of 5 compounds (r2pred = 0.924. The analyzed MFA model demonstrated a good fit, having r2 value of 0.868 and crossvalidated coefficient r2cv value of 0.771.

  2. Novel Chromone Derivatives from Marine Fungus Aspergillus versicolor Isolated from the Sponge Xestospongia exigua

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    From the marine sponge Xestospongia exigua, fungal isolates of Aspergillus versicolor (Vuill)Triab were obtained. Isolation and purification of ethyl acetate extracts from culture filtrates of the fungus led to yield six new chromone derivatives namely aspergione A, aspergione B, aspergione C, aspergione D, aspergione E, aspergione F. The structures of all the new compounds were established on the basis of extensive spectroscopy (UV, MS, 1H and 13C NMR, COSY, HMQC and HMBC) analysis.

  3. Homoleptic gold(i) N-heterocyclic allenylidene complexes: excited-state properties and lyotropic chromonics.

    Science.gov (United States)

    Xiao, Xin-Shan; Zou, Chao; Guan, Xiangguo; Yang, Chen; Lu, Wei; Che, Chi-Ming

    2016-03-29

    A series of phosphorescent Au(i) bis(N-heterocyclic allenylidene) complexes, namely [Au([double bond, length as m-dash]C[double bond, length as m-dash]C[double bond, length as m-dash]CR(1)R(2))2](+)X(-), were synthesized and structurally characterized. These organometallic complexes exhibit panchromatic transient absorption upon electronic photo-excitation and can self-organize into lyotropic chromonic mesophases in aqueous solutions. PMID:26928852

  4. Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities.

    Science.gov (United States)

    Proença, Carina; Albuquerque, Hélio M T; Ribeiro, Daniela; Freitas, Marisa; Santos, Clementina M M; Silva, Artur M S; Fernandes, Eduarda

    2016-06-10

    Chromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-yl]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O2(•-)), hydrogen peroxide (H2O2), hypochlorous acid (HOCl), singlet oxygen ((1)O2), and peroxyl radical (ROO(•))] and reactive nitrogen species (RNS) [nitric oxide ((•)NO) and peroxynitrite anion (ONOO(-))]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure-activity relationship. PMID:27031214

  5. Radioprotective effects of 2-imino-3[(chromone-2-yl)carbonyl]thiazolidines against γ-irradiation in mice

    International Nuclear Information System (INIS)

    A series of 2-imino-3-[(chromone-2-yl)carbonyl]thiazolidines substituted at the C-5 and/ or C-7 positions of a chromone ring were synthesized. The in vivo toxicity and radioprotective efficacy of these agents were evaluated in male NMRI mice against cobalt-60 γ-rays. The lethal dose 50% (LD50) values as determined by a Probit analysis, were 659, 1216 and 790 mg/kg for compounds, 2, 3 and 4, respectively. For studying radioprotective effects, one half of the toxic LD50 values were used, namely 330, 605 and 395 mg/kg for compounds 2, 3 and 4, respectively. The dose reduced factor (DRF) was determined by dividing the LD50/30 values obtained from the radiation survival curve in the presence of a radioprotective agent by the LD50/30 value obtained from a control radiation survival curve. A compound with a hydroxyl group substituent at the C-5 position afforded better radioprotective activity than those without this substituent. The radioprotective effect of chromone having a hydroxyl group at only the C-7 position was similar to that of the unsubstituted chromone. The most active compound has hydroxyl groups at the C-5 and C-7 positions of the chromone ring; it had a DRF of 1.48. (author)

  6. Orientations of Chromonic Liquid Crystals by Imprinted or Rubbed Polymer Films

    Science.gov (United States)

    Yi, Youngwoo; McGuire, Aya; Clark, Noel

    2014-03-01

    A variety of novel alignment effects of chromonic liquid crystal phases of sunset yellow (SSY)/water, disodium cromoglycate (DSCG)/water, and their mixtures by thiol-ene polymer films topographically imprinted with linear channels are observed using polarizing optical microscopy. Nematic DSCG and SSY at low concentration and their nematic mixtures orient with the long axes of stacked chromonic aggregates on average parallel to the channels, that is, with the molecular planes normal to the channel axis. On the contrary, nematic SSY in contact with the rubbed polyimide films orients with the long axes on average in-plane perpendicular to the rubbing direction, arguably, due to a tongue-groove interaction between SSY and the stretched PI chains. Furthermore, multi-stable alignments are observed in SSY solutions of sufficiently high concentration, including preferential in-plane orientation of the long axes of the aggregates parallel to, perpendicular to, and 45° rotated from the channels. This work was supported by NSF grant DMR 1207606, NSF MRSEC grant DMR 0820579, and NSF Research Experience for Undergraduate programs.

  7. Drying, phase separation, and deposition in droplets of sunset yellow chromonic liquid crystal

    Science.gov (United States)

    Gross, Adam; Davidson, Zoey S.; Huang, Yongyang; Still, Tim; Zhou, Chao; Yodh, A. G.

    We investigate the drying process and the final deposition patterns of multi-phase sessile droplets containing aqueous lyotropic chromonic liquid crystal (LC). The experiments employ a variety of optical techniques including profilometry, polarization optical microscopy and optical coherence microscopy. An unusual hierarchical LC assembly is observed during drying; in particular, LC mesogens are first formed at the start of drying and then compartments of isotropic, nematic and columnar phases arise. Nonuniform evaporation creates concentration gradients in droplets such that LC phases emerge from the outer edge of the drop and advance to the center over the course of drying. Distinct outward flows associated with the ``coffee-ring effect'' are seen initially, but the assembly of the mesogens creates viscosity, density, and surface tension gradients that effectively introduce new convective flows and complex LC phase boundaries within the drop. Finally, we show that the final deposit shape of chromonic materials changes with rate of evaporation. We gratefully acknowledge financial support through NSF DMR12-05463, MRSEC DMR11-20901, NASA NNX08AO0G, and NSF DBI-1455613.

  8. Characterization and Analysis of 2-(2-Phenylethyl)-chromone Derivatives from Agarwood (Aquilaria crassna) by Artificial Holing for Different Times.

    Science.gov (United States)

    Yang, Jinling; Dong, Wenhua; Kong, Fandong; Liao, Ge; Wang, Jun; Li, Wei; Mei, Wenli; Dai, Haofu

    2016-01-01

    A total of fifty-six chromones, including seven 5,6,7,8-tetrahydro-2-(2-phenylethyl)-chromones (THPECs), five 5,6-epoxy-2-(2-phenylethyl)chromones (EPECs), seven 5,6:7,8-diepoxy-2-(2-phenylethyl)chromones (DEPECs) and thirty-seven 2-(2-phenylethyl)chromones of the flidersia type (FTPECs), were characterized by HPLC/DAD/ESI/MS/MS in three agarwood samples (from Aquilaria crassna) induced by artificial holing with different holing times. The characteristic fragmentation behavior of DEPECs and EPECs, and the methods to distinguish these four types of chromones by MS analysis were described for the first time. In addition, it was found that the relative contents of DEPECs and EPECs were down-regulated, while the relative contents of THPECs and FTPECs were up-regulated for the samples from two, four and five years of the agarwood formation time. However, the relative contents of six most widespread and abundant FTPECs presented roughly upward based on the formation time. These results could be referenced to distinguish different agarwood samples collected from different formation time. PMID:27420040

  9. Polycyclic polyprenylated acylphloroglucinols and chromone O-glucosides from Hypericum henryi subsp. uraloides.

    Science.gov (United States)

    Chen, Xuan-Qin; Li, Yan; Cheng, Xiao; Wang, Kou; He, Juan; Pan, Zheng-Hong; Li, Ming-Ming; Peng, Li-Yan; Xu, Gang; Zhao, Qin-Shi

    2010-01-01

    Two new C(30)-epimeric polycyclic polyprenylated acylphloroglucinols (PPAPs), named uralodins B and C (1 and 2, resp.), were isolated from the aerial parts of Hypericum henryi subsp. uraloides together with two new chromone glucosides, urachromones A and B (3 and 4, resp.), as well as 16 known compounds. Their structures were established by extensive NMR techniques and MS analysis. The epimers 1 and 2 always behaved like a single compound when examined by TLC, and were separated by HPLC. Their configuration was distinguished by comparative analysis of the NMR data with known analogues together with the ROESY experiment. All the isolated PPAPs were evaluated for their cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines. Compound 1 showed modest cytotoxic activities against SGC7901 and HL-60 cell lines, and 2 showed modest cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines. PMID:20087990

  10. Highly oxygenated chromones from mangrove-derived endophytic fungus Rhytidhysteron rufulum.

    Science.gov (United States)

    Chokpaiboon, Supichar; Choodej, Siwattra; Boonyuen, Nattawut; Teerawatananond, Thapong; Pudhom, Khanitha

    2016-02-01

    Five highly oxygenated chromones, rhytidchromones A-E, were isolated from the culture broth of a mangrove-derived endophytic fungus, Rhytidhysteron rufulum, isolated from Thai Bruguiera gymnorrhiza. Their structures were determined by analysis of 1D and 2D NMR spectroscopic data. The structure of rhytidchromone A was further confirmed by single-crystal X-ray diffraction analysis. These compounds were evaluated for cytotoxicity against four cancer cell lines (MCF-7, Hep-G2, Kato-3 and CaSki). All compounds, except for rhytidchromone D, displayed cytotoxicity against Kato-3 cell lines with IC50 values ranging from 16.0 to 23.3μM, while rhytidchromones A and C were active against MCF-7 cells with IC50 values of 19.3 and 17.7μM, respectively. PMID:26712613

  11. Charge carrier trapping in highly-ordered lyotropic chromonic liquid crystal films based on ionic perylene diimide derivatives

    OpenAIRE

    Soroka, Pavlo V.; Vakhnin, Alexander Yu; Skryshevskiy, Yuriy A; Boiko, Oleksandr P.; Anisimov, Maksim I; Slominskiy, Yuriy L; Nazarenko, Vassili G.; Genoe, Jan; Kadashchuk, Andrey

    2014-01-01

    Charge carrier trapping in thin films of lyotropic chromonic liquid crystals (LCLCs) based on ionic perylene diimide derivative and in chemically-similar neutral N,N′-dipentyl-3,4,9,10-perylene-dicarboximide (PTCDI-C5) films is investigated by thermally-stimulated luminescence (TSL) technique. The LCLC films comprise elongated molecular aggregates featuring a long-range orientational order. The obtained results provide direct evidence for the improved energetic ordering (smaller effective ene...

  12. Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

    OpenAIRE

    Elver Otero; Sebastián Vergara; Sara M. Robledo; Wilson Cardona; Miguel Carda; Vélez, Ivan D; Carlos Rojas; Felipe Otálvaro

    2014-01-01

    Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7–9 and 17, were active against Leishmani...

  13. Lyotropic chromonic liquid crystals: From viscoelastic properties to living liquid crystals

    Science.gov (United States)

    Zhou, Shuang

    Lyotropic chromonic liquid crystal (LCLC) represents a broad range of molecules, from organic dyes and drugs to DNA, that self-assemble into linear aggregates in water through face-to-face stacking. These linear aggregates of high aspect ratio are capable of orientational order, forming, for example nematic phase. Since the microscopic properties (such as length) of the chromonic aggregates are results of subtle balance between energy and entropy, the macroscopic viscoelastic properties of the nematic media are sensitive to change of external factors. In the first part of this thesis, by using dynamic light scattering and magnetic Frederiks transition techniques, we study the Frank elastic moduli and viscosity coefficients of LCLC disodium cromoglycate (DSCG) and sunset yellow (SSY) as functions of concentration c , temperature T and ionic contents. The elastic moduli of splay (K1) and bend (K3) are in the order of 10pN, about 10 times larger than the twist modulus (K2). The splay modulus K1 and the ratio K1/K3 both increase substantially as T decreases or c increases, which we attribute to the elongation of linear aggregates at lower T or higher c . The bend viscosity is comparable to that of thermotropic liquid crystals, while the splay and twist viscosities are several orders of magnitude larger, changing exponentially with T . Additional ionic additives into the system influence the viscoelastic properties of these systems in a dramatic and versatile way. For example, monovalent salt NaCl decreases bend modulus K3 and increases twist viscosity, while an elevated pH decreases all the parameters. We attribute these features to the ion-induced changes in length and flexibility of building units of LCLC, the chromonic aggregates, a property not found in conventional thermotropic and lyotropic liquid crystals form by covalently bound units of fixed length. The second part of the thesis studies a new active bio-mechanical hybrid system called living liquid crystal

  14. Antibacterial, antifungal and cytotoxic properties of some sulfonamide-derived chromones.

    Science.gov (United States)

    Chohan, Zahid H; Rauf, Abdul; Naseer, Muhammad M; Somra, Muhammad A; Supuran, Claudiu T

    2006-04-01

    A series of antibacterial and antifungal sulfonamide (sulfanilamide, sulfaguanidine, sulfamethaxozole, 4-aminoethylbenzene-sulfonamide and 4-amino-6-trifluoromethyl-benzene-1,3-disulfonamide) derived chromones, previously reported as inhibitors of carbonic anhydrase, have been screened for in-vitro antibacterial activity against four Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi and Shigella flexener) and two Gram-positive (Bacillus subtilis and Staphylococcus aureus) bacterial strains, and for in-vitro antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani, Candida glaberata. All compounds (1)-(5) showed significant antibacterial activity against all four Gram-negative species and both Gram-positive species. However, three of them, (1), (4) and (5), were found to be comparatively much more active compared to (2) and (3). Of these, (5) was found to be the most active one. For antifungal activity, generally compounds (1) and (2) showed significant activity against more than three strains whereas (3)-(5) also showed significant activity against varied fungal strains. In the brine shrimp bioassay for in-vitro cytotoxic properties, only two compounds, (4) and (5) displayed potent cytotoxic activity, LD50 = 2.732 x 10(-4)M) and LD50 = 2.290 x 10(-4)M) respectively, against Artemia salina. PMID:16789431

  15. Phase behavior of chromonic liquid crystal mixtures of Sunset Yellow and Disodium Cromoglycate

    Science.gov (United States)

    Yamaguchi, Akihiro; Smith, Gregory; Yi, Youngwoo; Xu, Charles; Biffi, Silvia; Serra, Francesca; Bellini, Tommaso; Clark, Noel

    2014-03-01

    Chromonic liquid crystals (CLCs) are formed when planar molecules dissolved in water stack into rod-like aggregates that can order as liquid crystals. Isotropic, nematic, and M-phases can be observed depending on the degree of molecular orientational and positional order by variation of the CLC concentration. We focused on mixtures of two well-known CLCs, Sunset Yellow, a food dye, and disodium cromoglycate (DSCG), an asthma medication. In order to study the phase behaviors of these mixtures, we observed their textures in glass cells and capillaries using polarized light microscopy. We report here a ternary phase diagram describing the complete phase behavior of the CLC mixtures. We observed a variety of phase behaviors depending on species ratio and concentration. In the isotropic phase, no clear phase separation of the two dyes was observed, while separation did occur in many nematic and M-phase combinations. We will also describe phase observations made using a light spectroscopy and bulk centrifugal partitioning. Grant support: NSF DMR 1207606 and NSF MRSEC DMR-0820579.

  16. Fine structure of the topological defect core: Disclination in lyotropic chromonic liquid crystal

    Science.gov (United States)

    Zhou, Shuang; Shiyanovskii, Sergij; Park, Heung-Shik; Kim, Young-Ki; Hearn, Tristan; Reichel, Lothar; Lavrentovich, Oleg

    Topological defects represent an important concept in many branches of modern physics ranging from cosmology and optics to hard and soft matter. One of the most difficult problems is the fine structure of the so-called core region of defects, where the deformations of the order parameter are so strong that the phenomenological description valid in the far field becomes invalid. Experimental exploration of the fine core structure is usually hindered by the small size (atomic/molecular level) of the core, where optical or even electron microscopy techniques are invalid. In this work, we take advantage of the peculiar nature of the so-called lyotropic chromonic liquid crystals (LCLC) of a nematic type that carry disclinations with a core extending over macroscopic distances (tens of micrometers), large enough to explore their spatial variation by optical and electron microscopy. We demonstrate that the director and the scalar order parameter (associated with the degree of orientational order) show a profound change in the core region. In particular, as one approaches the center of the defect, the azimuthal dependency of the director field changes dramatically and the scalar order parameter shows a strong dependence on the strength of splay and bend deformations. This work is supported by NSF Grant DMS-1434185.

  17. Flexible and Patterned Thin Film Polarizer: Photopolymerization of Perylene-based Lyotropic Chromonic Reactive Mesogens.

    Science.gov (United States)

    Im, Pureun; Kang, Dong-Gue; Kim, Dae-Yoon; Choi, Yu-Jin; Yoon, Won-Jin; Lee, Myong-Hoon; Lee, In-Hwan; Lee, Cheul-Ro; Jeong, Kwang-Un

    2016-01-13

    A perylene-based reactive mesogen (DAPDI) forming a lyotropic chromonic liquid crystal (LCLC) phase was newly designed and synthesized for the fabrication of macroscopically oriented and patterned thin film polarizer (TFP) on the flexible polymer substrates. The anisotropic optical property and molecular self-assembly of DAPDI were investigated by the combination of microscopic, scattering and spectroscopic techniques. The main driving forces of molecular self-assembly were the face-to-face π-π intermolecular interaction among aromatic cores and the nanophase separation between hydrophilic ionic groups and hydrophobic aromatic cores. Degree of polarization for the macroscopically oriented and photopolymerized DAPDI TFP was estimated to be 99.81% at the λmax = 491 nm. After mechanically shearing the DAPDI LCLC aqueous solution on the flexible polymer substrates, we successfully fabricated the patterned DAPDI TFP by etching the unpolymerized regions selectively blocked by a photomask during the photopolymerization process. Chemical and mechanical stabilities were confirmed by the solvent and pencil hardness tests, and its surface morphology was further investigated by optical microscopy, atomic force microscopy, and three-dimensional surface nanoprofiler. The flexible and patterned DAPDI TFP with robust chemical and mechanical stabilities can be a stepping stone for the advanced flexible optoelectronic devices. PMID:26616135

  18. X-ray microscopy study of chromonic liquid crystal dry film texture.

    Science.gov (United States)

    Kaznatcheev, K V; Dudin, P; Lavrentovich, O D; Hitchcock, A P

    2007-12-01

    Soft x-ray spectromicroscopy has been used to investigate the degree of the molecular alignment of sulfonated benzo[de]benzo[4.5]imidazo[2,1-a]isoquinoline[7,1], a lyotropic chromonic liquid crystal (LCLC). LCLC thin films cast from concentrated aqua solution (20%wt.) , aligned by shear flow and dried, show strong linear dichroism in their C-, N-, O-, S- K edge near edge x-ray spectra (NEXAFS). The carbon K edge has been used for quantitative evaluation of the orientational texture of the films at a submicron spatial scale. This has verified there is predominantly in-plane alignment of the LC director. To highlight the role of hydrophobic-hydrophilic interactions, two stereoisomers of the same dye has been synthesized with different positioning of terminal sulfonate groups, in the form of a mixture of isomers with sulfonate groups in 2,10 and 2,11 positions (Y104 compound) and in a 5,10-disulfo arrangement (Y105). Both compounds develop characteristic herringbone-type texture with similar domain sizes. Polarized optical microscopy and higher resolution x-ray microscopy show sinusoidal-like undulations of the molecular director, with occasional crisscross appearance. Such behavior is found to be consistent with earlier observation of striations, characteristic of the columnar phase. The drastic difference in the degree of undulation ( +/-15 degrees in Y104 and +/-7 degrees in Y105 films) and long period of undulation (approaching the film thickness) requires further analysis. It was also found that the degree of in-plane order within domains changes from 0.8 for Y104 to >0.9 in Y105 films. PMID:18233857

  19. X-ray microscopy study of chromonic liquid crystal dry film texture

    International Nuclear Information System (INIS)

    Soft x-ray spectromicroscopy has been used to investigate the degree of the molecular alignment of sulfonated benzo[de]benzo[4.5]imidazo[2,1-a]isoquinoline[7,1], a lyotropic chromonic liquid crystal (LCLC). LCLC thin films cast from concentrated aqua solution (20 % wt.), aligned by shear flow and dried, show strong linear dichroism in their C-, N-, O-, S-K edge near edge x-ray spectra (NEXAFS). The carbon K edge has been used for quantitative evaluation of the orientational texture of the films at a submicron spatial scale. This has verified there is predominantly in-plane alignment of the LC director. To highlight the role of hydrophobic-hydrophilic interactions, two stereoisomers of the same dye has been synthesized with different positioning of terminal sulfonate groups, in the form of a mixture of isomers with sulfonate groups in 2,10 and 2,11 positions (Y104 compound) and in a 5,10-disulfo arrangement (Y105). Both compounds develop characteristic herringbone-type texture with similar domain sizes. Polarized optical microscopy and higher resolution x-ray microscopy show sinusoidal-like undulations of the molecular director, with occasional crisscross appearance. Such behavior is found to be consistent with earlier observation of striations, characteristic of the columnar phase. The drastic difference in the degree of undulation (±15 deg. in Y104 and ±7 deg. in Y105 films) and long period of undulation (approaching the film thickness) requires further analysis. It was also found that the degree of in-plane order within domains changes from 0.8 for Y104 to >0.9 in Y105 films

  20. Charge carrier trapping in highly-ordered lyotropic chromonic liquid crystal films based on ionic perylene diimide derivatives

    Science.gov (United States)

    Soroka, Pavlo V.; Vakhnin, Alexander Yu.; Skryshevskiy, Yuriy A.; Boiko, Oleksandr P.; Anisimov, Maksim I.; Slominskiy, Yuriy L.; Nazarenko, Vassili G.; Genoe, Jan; Kadashchuk, Andrey

    2014-12-01

    Charge carrier trapping in thin films of lyotropic chromonic liquid crystals (LCLCs) based on ionic perylene diimide derivative and in chemically-similar neutral N,N'-dipentyl-3,4,9,10-perylene-dicarboximide (PTCDI-C5) films is investigated by thermally-stimulated luminescence (TSL) technique. The LCLC films comprise elongated molecular aggregates featuring a long-range orientational order. The obtained results provide direct evidence for the improved energetic ordering (smaller effective energetic disorder) in aggregated LCLC films as compared to conventional PTCDI-C5 films. The width of the density-of-state distribution of 0.09 eV and 0.13 eV was estimated for the LCLC and PTCDI-C5 films, respectively. Relatively small effective energetic disorder in LCLC films is ascribed to formation of macroscopically larger LCLC aggregates.

  1. Optimization of chromone-2-carboxamide melanin concentrating hormone receptor 1 antagonists: assessment of potency, efficacy, and cardiovascular safety.

    Science.gov (United States)

    Lynch, John K; Freeman, Jennifer C; Judd, Andrew S; Iyengar, Rajesh; Mulhern, Mathew; Zhao, Gang; Napier, James J; Wodka, Dariusz; Brodjian, Sevan; Dayton, Brian D; Falls, Doug; Ogiela, Christopher; Reilly, Regina M; Campbell, Thomas J; Polakowski, James S; Hernandez, Lisa; Marsh, Kennan C; Shapiro, Robin; Knourek-Segel, Victoria; Droz, Brian; Bush, Eugene; Brune, Michael; Preusser, Lee C; Fryer, Ryan M; Reinhart, Glenn A; Houseman, Kathryn; Diaz, Gilbert; Mikhail, Ann; Limberis, James T; Sham, Hing L; Collins, Christine A; Kym, Philip R

    2006-11-01

    Evaluation of multiple structurally distinct series of melanin concentrating hormone receptor 1 antagonists in an anesthetized rat cardiovascualar assay led to the identification of a chromone-2-carboxamide series as having excellent safety against the chosen cardiovascular endpoints at high drug concentrations in the plasma and brain. Optimization of this series led to considerable improvements in affinity, functional potency, and pharmacokinetic profile. This led to the identification of a 7-fluorochromone-2-carboxamide (22) that was orally efficacious in a diet-induced obese mouse model, retained a favorable cardiovascular profile in rat, and demonstrated dramatic improvement in effects on mean arterial pressure in our dog cardiovascular model compared to other series reported by our group. However, this analogue also led to prolongation of the QT interval in the dog that was linked to affinity for hERG channel and unexpectedly potent functional blockade of this ion channel. PMID:17064075

  2. Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

    Directory of Open Access Journals (Sweden)

    Elver Otero

    2014-08-01

    Full Text Available Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7–9 and 17, were active against Leishmania parasites (EC50 = 9.4; 10.2; 13.5 and 27.5 µg/mL, respectively and showed no toxicity toward mammalian cells (>200 µg/mL. They are potential candidates for antileishmanial drug development. Compounds 25–27, were active and cytotoxic. Further studies using other cell types are needed in order to discriminate whether the toxicity shown by these compounds is against tumor or non-tumor cells. The results indicate that compounds containing small alkyl chains show better selectivity indices. Moreover, Michael acceptor moieties may modify both the leishmanicidal activity and cytotoxicity. Further studies are required to evaluate if the in vitro activity against Leishmania panamensis demonstrated here is also observed in vivo.

  3. Antioxidant activities of some new chromonyl-2,4-thiazolidinediones and chromonyl-2,4-imidazolidinediones having chromone cores.

    Science.gov (United States)

    Berczyński, Paweł; Kładna, Aleksandra; Kruk, Irena; Piechowska, Teresa; Aboul-Enein, Hassan Y; Bozdağ-Dündar, Oya; Ceylan-Unlusoy, Meltem

    2013-11-01

    The antioxidant properties of 11 new synthesized chromonyl-2,4-thiazolidinediones and chromonyl-2,4-imidazolidinediones (CBs) were investigated. The antioxidant activities and mechanisms of the CBs interaction with reactive oxygen species (ROS) were clarified using various in vitro antioxidant assay methods including superoxide anion radical (O2(•-)), hydroxyl radical (HO(•)), 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH(•)) scavenging activity and the iron (II)-ferrozine complex formation. The potassium superoxide/18-crown-6 ether dissolved in dimethylsulfoxide (DMSO) was applied as a source of superoxide anion radical. Hydroxyl radicals were produced in the Fenton-like reaction Fe(II)+H2O2. Chemiluminescence, spectrophotometry, and electron paramagnetic resonance (EPR) spectroscopy using 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) as spin trap were applied as the measurement techniques. The CBs examined that exhibited good free radical scavenging activity also showed strong total antioxidant power capacity. Possible mechanisms of antioxidation are proposed to explain the differences in the experimental results between the chromone derivatives with imidazolidine-2,4-dione ring and those with thiazolidine-2,4-dione ring. In conclusion, some of the new CBs are promising to be applied as inhibitors of free radicals. PMID:23860947

  4. Oxalicumone A, a new dihydrothiophene-condensed sulfur chromone induces apoptosis in leukemia cells through endoplasmic reticulum stress pathway.

    Science.gov (United States)

    Wang, Jie; Wang, Qiao-Li; Nong, Xu-Hua; Zhang, Xiao-Yong; Xu, Xin-Ya; Qi, Shu-Hua; Wang, Yi-Fei

    2016-07-15

    Oxalicumone A (POA1), a novel dihydrothiophene-condensed sulfur chromone isolated from the marine fungus Penicillium oxalicum SCSGAF 0023, showed cytotoxicity against several cancer cells previously. In this study, its anti-cancer activity and underlying mechanism of this action were investigated in leukemia cells like KG-1a, HL60, U937, and K562. The results showed that POA1 inhibited dose-/time-dependently cell growth and induced apoptosis in leukemia cells. Also, POA1 caused cleavages of caspase-3, 8, 9 and PARP1, loss of mitochondrial membrane potential, up-regulations of phosphorylated p38 and JNK, and activation of endoplasmic reticulum stress (ER stress). Furthermore, 4-PBA (an ER stress inhibitor) but not SP600125 and SB203580 (JNK and p38 inhibitor, respectively) could largely inhibit POA1-induced growth suppression. Additionally, 4-PBA obstructed mitochondrial depolarization and cleavage of PARP1. These data suggested that ER stress pathway might be an important mediator in POA1-induced apoptosis. In conclusion, POA1 may have antitumor effects in leukemia cells through the induction of ER stress pathway. PMID:27132813

  5. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW 3-METHYL-2- PHENYLSPIRO[PYRANO[2,3-f]CHROMONE-8,1'-CYCLOALKAN/8,4'-PIPERIDIN]-4,10-DIONES SYNTHESIS und antibakterielle Wirksamkeit von NEW 3-METHYL-2- PHENYLSPIRO [pyrano [2,3-f] chromon-8, 1'-CYCLOALKAN / 8,4 '-piperidin] -4,10 -DIONE

    Directory of Open Access Journals (Sweden)

    Sreenivas Peddolla and David Krupadanam. G. L

    2011-04-01

    Full Text Available 3-Methyl-2-phenylspiro[pyrano[2,3-f]chromone-8,1'-cycloalkan/8,4'-piperidin]-4,10-diones (8a-e were synthesized from 8-acetyl-7-hydroxy-3-methylflavone and cycloalkanones/N-substituted piperidones with pyrrolidine as catalyst. All the compounds were tested in vitro for their antibacterial activity against Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus and Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa. Three compounds 8c, 8d and 8e have displayed very good antibacterial activity.

  6. Influence of Proton and Salt Concentration on the Chromonic Liquid Crystal Phase Diagram of Disodium Cromoglycate Solutions: Prospects and Limitations of a Host for DNA Nanostructures.

    Science.gov (United States)

    Zhang, Bingru; Kitzerow, Heinz-S

    2016-03-31

    Lyotropic chromonic liquid crystals have recently been suggested for use as a self-organized host for dispersing and aligning self-organized DNA origami nanostructures. However, an appropriate pH value and a suitable cation concentration are necessary to stabilize such nanostructures and to avoid unfolding of the DNA. The present study shows that the nematic and columnar liquid crystal phases appearing in aqueous solutions of disodium cromoglycate are robust against the replacement of deionized water by a neutral or alkaline buffer solution. However, disodium cromoglycate precipitates when an acidic buffer is used or when the concentration of magnesium cations exceeds a critical concentration of about 0.6-0.7 mmol/L. PMID:26964003

  7. MICROWAVE ASSISTED SYNTHESIS AND BIOLOGICAL EVALUATION OF 2-ARYL/HETERYL-3-ARYLOXY/HETERYLOXY-4H-CHROMONES (4-OXO-2-ARYL/HETERYL-4H-CHROMEN-3-Yl-CARBOXYLATE

    Directory of Open Access Journals (Sweden)

    Mangesh P. Gharpure

    2013-03-01

    Full Text Available 2-Aryl/heteryl-3-aryloxy/heteryloxy-4H-chromones 5 have been synthesized through a series of reactions starting from phenols under microwave irradiation. This process is an effective alternative to the traditional thermal heating method. The yields are excellent and the reaction time is in a few minutes. These compounds have been characterized on the basis of IR, 1H NMR, 13C NMR and Mass spectrometry and evaluated for antibacterial activity.

  8. The inhibition of substance P-induced histamine release from mast cells by 6, 7-dihydro-6, 8, 8, 10-tetramethyl-8H-pyrano-[3, 2-g] chromone-2-carboxylic acid (EAA).

    OpenAIRE

    Tsutsumi, Koji; Nishibori, Masahiro; Saeki, Kiyomi

    1984-01-01

    In the presence of extracellular Ca2+, 6,7-dihydro-6,8,8, 10-tetramethyl-8H-pyrano [3, 2-g] chromone-2-carboxylic acid (EAA) had an inhibitory effect on the substance P-induced histamine release from rat peritoneal mast cells. Not only Ca2+ but also Mg2+, Sr2+ and Ba2+ were effective in enhancing the activity of EAA. Marked tachyphylaxis to EAA developed irrespective of the presence or absence of extracellular Ca2+. Cross-tachyphylaxis was observed between EAA and disodium cromoglycate (DSCG)...

  9. The inhibition of substance P-induced histamine release from mast cells by 6, 7-dihydro-6, 8, 8, 10-tetramethyl-8H-pyrano-[3, 2-g] chromone-2-carboxylic acid (EAA.

    Directory of Open Access Journals (Sweden)

    Tsutsumi,Koji

    1984-08-01

    Full Text Available In the presence of extracellular Ca2+, 6,7-dihydro-6,8,8, 10-tetramethyl-8H-pyrano [3, 2-g] chromone-2-carboxylic acid (EAA had an inhibitory effect on the substance P-induced histamine release from rat peritoneal mast cells. Not only Ca2+ but also Mg2+, Sr2+ and Ba2+ were effective in enhancing the activity of EAA. Marked tachyphylaxis to EAA developed irrespective of the presence or absence of extracellular Ca2+. Cross-tachyphylaxis was observed between EAA and disodium cromoglycate (DSCG. These results indicate that the mode of action of EAA is similar, but not identical, with that of DSCG.

  10. Synthesis, characterization, and antioxidant/cytotoxic activity of new chromone Schiff base nano-complexes of Zn(II), Cu(II), Ni(II) and Co(II)

    Science.gov (United States)

    Saif, M.; El-Shafiy, Hoda F.; Mashaly, Mahmoud M.; Eid, Mohamed F.; Nabeel, A. I.; Fouad, R.

    2016-08-01

    A chromone Schiff base complexes of Zn(II) (1), Cu(II) (2), Ni(II) (3) and Co(II) (4) were successfully prepared in nano domain with crystalline or amorphous structures. The spectroscopic data revealed that the Schiff base ligand behaves as a monoanionic tridentate ligand. The metal complexes exhibited octahedral geometry. Transmission electron microscope (TEM) analysis showed that Cu(II) complex have aggregated nanospheres morphology. The obtained nano-complexes were tested as antioxidant and antitumor agents. The H2L and its Cu(II) complex (2) were found to be more potent antioxidant (IC50(H2L) = 0.93 μM; IC50(Cu(II) complex) = 1.1 μM than standard ascorbic acid (IC50 = 2.1 μM) as evaluated by DPPH• method. The H2L and its complexes (1-4) were tested for their in vitro cytotoxicity against Ehrlich Ascites Carcinoma cell line (EAC). The Cu(II) nano-complex (2) effectively inhibited EAC growth with IC50 value of 47 μM in comparison with its parent compound and other prepared complexes. The high antioxidant activity and antitumor activity of Cu(II) nano-complex (2) were attributed to their chemical structure, Cu(II) reducing capacity, and nanosize property. The toxicity test on mice showed that Zn(II) (1) and Cu(II) (2) nano-complex have lower toxicity than the standard cis-platin.

  11. Chromone derivatives as antioxidant agents : the structural variable

    OpenAIRE

    Machado, Nelson Filipe Lopes

    2012-01-01

    Devido ao facto do stress oxidativo ter vindo a ser relacionado com diversos estados patológicos graves, desde doenças cardiovasculares e neurodegenerativas a cancro, o desenvolvimento de agentes oxidantes mais eficientes, a partir de compostos de origem natural, tem sido alvo de pesquisa intensa na última década, com o objectivo de desenvolver novas estratégias de prevenção de várias patologias que constituem presentemente algumas das principais causas de morte em todo o mundo. Os deri...

  12. Synthesis, spectroscopic characterization and electrochemical studies of Girard's T chromone complexes

    Science.gov (United States)

    Al-Saeedi, Sameerah I.; Alaghaz, Abdel-Nasser M. A.; Ammar, Reda A.

    2016-05-01

    Complexes of cobalt(II), nickel(II), copper(II) and zinc(II) of general composition [M(L)2] have been. The elemental analyses, molar conductance, spectral, magnetic moment and thermal measurements studies of the compounds led to the conclusion that the ligand acts as a tridentate manner (OON). The molar conductance of the metal complexes in fresh solution of DMSO lies in the range of 8.10-10.18 Ω-1 cm2 mol-1 indicating their non-electrolytic behavior. On the basis of analytical and spectroscopic techniques, octahedral geometry of the complexes was proposed. The ligand field parameters were calculated for Co(II), Ni(II) and Cu(II) complexes and their values were found in the range reported for a octahedral structure. The data show that the complexes have composition of ML2 type. The activation of thermodynamic parameters are calculated using different equations. The octahedral geometry of the complexes is confirmed using DFT method from DMOL3 calculations and ligand field parameters. The cyclic voltammograms of the Cu(II)/Co(II)/Ni(II) complexes investigated in DMSO solution exhibit metal centered electroactivity in the potential range -1.5 to +1.5 V. The electrochemical data obtained for Cu(II) complexes explains the change of structural arrangement of the ligand around Cu(II) ions.

  13. High Magnetic Field-Induced Birefringence in Lyotropic Chromonic Liquid Crystals

    Science.gov (United States)

    Ostapenko, T.; Nastishin, Yu.; Gleeson, J. T.; Sprunt, S. N.; Lavrentovich, O. D.; Collings, P. J.

    2009-03-01

    We studied the effect of magnetic-field induced birefringence of a 14% solution of disodium cromoglycate (DSCG) in water at temperatures above the nematic-isotropic coexistence region. According to Landau-deGennes mean field theory, we expect to find a linear relationship between the inverse of the induced birefringence, δn, and the quantity (T-T*), where T* is the stability limit of the isotropic phase. Using the 31 T resistive magnet at the National High Magnetic Field Laboratory, we observed that, as we increase the temperature above the coexistence region, we deviate from this linear dependence. Our data shows that δn goes to zero, whereas Landau-deGennes predicts that δn should decrease asymptotically. This may be due to the lack of isodesmic aggregate formation at a finite temperature above the coexistence region.Supported by NSF (DMR-0710544 and DMR-0606160). Work performed at NHMFL, supported by NSF cooperative agreements DMR-0084173, the State of Florida and the DOE.

  14. A new cytotoxic 2-(2-phenylethyl)chromone from Chinese eaglewood

    Institute of Scientific and Technical Information of China (English)

    Jun Liu; Jiao Wu; You Xing Zhao; Yuan Yuan Deng; Wen Li Mei; Hao Fu Dai

    2008-01-01

    A new compound 8-chloro-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (1) was isolated from the Chinese eaglewood [Aquilaria sinensis (Lour.) Gilg]. Its structure was elucidated on the basis of spectral data. Compound 1 showed cytotoxicity against human gastric cancer cell line (SGC-7901) in vitro by MTT method with the IC50 value of 14.6 μg/mL.

  15. Liquid Crystals: Alignment and Graphene-Assisted Decoration of Lyotropic Chromonic Liquid Crystals Containing DNA Origami Nanostructures (Small 12/2016).

    Science.gov (United States)

    Martens, Kevin; Funck, Timon; Kempter, Susanne; Roller, Eva-Maria; Liedl, Tim; Blaschke, Benno M; Knecht, Peter; Garrido, José Antonio; Zhang, Bingru; Kitzerow, Heinz

    2016-03-01

    On page 1658, H. Kitzerow and co-workers show that stable dispersion of the nanostructures in a liquid crystal and uniform alignment of the resulting composite are possible. DNA origami nanostructures decorated with gold nanoparticles (inset: TEM image) are dispersed in a uniformly aligned liquid crystal (background: image observed by polarizing microscopy). The unusual optical properties of such plasmonic nanostructures - for example a large circular dichroism in the case of the nanohelix - are expected to be enhanced if the nanostructures are uniformly aligned. PMID:27000497

  16. Structure determination of some oxygen and nitrogen heterocyclic compounds by NMR

    OpenAIRE

    Seixas, Raquel; Esteves, Cátia; Brito, Cristela; Leal, Stephanie; Pinto, Diana; Santos, Clementina M.M.; Seca, Ana; Silva, Artur; Cavaleiro, José

    2012-01-01

    Oxygen heterocyclic compounds are widely distributed in Nature, being chromone and xanthone derivatives some examples. For instance, the xanthone ring system is a structural motif prevalent in higher plants such as those of Guttiferae and Gentianaceae families.1 Both natural and synthetic derivatives often endowed with interesting pharmacological properties, such as anti-inflammatory,2 antitumour3 and antioxidant activities.4 Chromones and chromone derivatives play an important role in ...

  17. Synthesis and transformation of halochromones

    OpenAIRE

    Tomé, Sara M.; Silva, Artur; Santos, Clementina M.M.

    2014-01-01

    Chromones (4H-1-benzopyran-4-ones) are one of the most abundant groups of naturally occurring oxygen containing heterocyclic compounds possessing a benzo-γ-pyrone framework, 1a. The significance of these widely spread and highly diverse compounds is far beyond the important biological functions they assume in nature [1, 2]. Natural and synthetic chromone derivatives have been assigned as lead structures in drug development with some already being marketed [3]. The majo...

  18. Benzopyrones. 14. Synthesis and antiallergic properties of some N-tetrazolylcarboxamides and related compounds.

    Science.gov (United States)

    Ellis, G P; Becket, G J; Shaw, D; Wilson, H K; Vardey, C J; Skidmore, I F

    1978-11-01

    A series of chromones containing an acidic group has been synthesized and screened for the ability to inhibit passive cutaneous anaphylaxis and the release of histamine from mast cells of the rat. Many of the chromones contain the N-(5-tetrazolyl)carboxamido group, a novel source of acidity. Others contain a carboxyl, C-(5-tetrazolyl), 5-(4H)-oxotetrazolinyl, or N-(5-tetrazolyl)sulfonamido function. The compounds were compared with cromolyn sodium (sodium cromoglycate) and many were found to be powerful inhibitors of anaphylaxis. The most potent was 7-methoxy-4-oxo-N-(5-tetrazolyl)-4H-1-benzopyran-2-carboxamide (15). Structure-activity relationships among the chromones and also some related compounds are discussed. PMID:82617

  19. Synthesis and characterisation of new 4-oxo-N-(substituted-thiazol-2-yl)-4H-chromene-2-carboxamides as potential adenosine receptor ligands

    Science.gov (United States)

    Cagide, Fernando; Borges, Fernanda; Gomes, Ligia R.; Low, John Nicolson

    2015-06-01

    Chromones are 4H-benzopyran-4-one heterocycles that have been thoroughly studied due to their interesting biological activities. Thiazole based compounds have been used in therapeutics as antimicrobial, antiviral and as antifungal agents for a long time but, in the past decades, they have been identified as potent and selective ligands for adenosine receptor. In continuation of our project related to the syntheses of pharmacologically important heterocycles, a new series of chromone-thiazole hybrids have been designed as potential ligands for human adenosine receptors. In this context, new 4-oxo-N-(substituted-thiazol-2-yl)-4H-chromene-2-carboxamides were synthesized from chromone-2-carboxylic acid by two different amidation methods. The development of dissimilar synthetic approaches provided the possibility of working with diverse reaction conditions, namely with conventional heating and/or microwave irradiation. The structure of the compounds has been established on the basis of NMR and MS spectroscopy and X-ray crystallography. Relevant data related to the molecular geometry and conformation of the chromone-thiazole hybrids has been acquired which can be of the utmost importance to understand ligand-receptor binding.

  20. Phases and structures of sunset yellow and disodium cromoglycate mixtures in water

    Science.gov (United States)

    Yamaguchi, Akihiro; Smith, Gregory P.; Yi, Youngwoo; Xu, Charles; Biffi, Silvia; Serra, Francesca; Bellini, Tommaso; Zhu, Chenhui; Clark, Noel A.

    2016-01-01

    We study phases and structures of mixtures of two representative chromonic liquid crystal materials, sunset yellow FCF (SSY) and disodium cromoglycate (DSCG), in water. A variety of combinations of isotropic, nematic (N ), and columnar (also called M ) phases are observed depending on their concentrations, and a phase diagram is made. We find a tendency for DSCG-rich regions to show higher-order phases while SSY-rich regions show lower-order ones. We observe uniform mesophases only when one of the materials is sparse in the N phases. Their miscibility in M phases is so low that essentially complete phase separation occurs. X-ray scattering and spectroscopy studies confirm that SSY and DSCG molecules do not mix when they form chromonic aggregates and neither do their aggregates when they form M phases.

  1. Isoeugenin, a Novel Nitric Oxide Synthase Inhibitor Isolated from the Rhizomes of Imperata cylindrica

    OpenAIRE

    Hyo-Jin An; Agung Nugroho; Byong-Min Song; Hee-Juhn Park

    2015-01-01

    Phytochemical studies on the constituents of the rhizomes of Imperata cylindrica (Gramineae) were performed using high-performance liquid chromatography (HPLC). We also aimed to search for any biologically active substance capable of inhibiting nitric oxide (NO) formation in lipopolysaccharide (LPS)-activated macrophage 264.7 cells, by testing four compounds isolated from this plant. Four compounds, including a new chromone, isoeugenin, along with ferulic acid, p-coumaric acid, and caffeic ac...

  2. Hierarchical Organization in Liquid Crystal-in-Liquid Crystal Emulsions

    OpenAIRE

    Mushenheim, Peter C.; Abbott, Nicholas L.

    2014-01-01

    We report the formation and characterization of hierarchical ordering in systems comprised of micrometer-sized droplets of thermotropic nematic liquid crystals (LCs) dispersed in continuous nematic phases of a lyotropic chromonic LC (disodium cromoglycate (DSCG)). Significantly, we find the orientations of the two LC phases to be coupled, with nematic droplets of 4′-pentyl-4-cyanobiphenyl (5CB) exhibiting a bipolar configuration with an axis of symmetry aligned orthogonal to the far-field dir...

  3. The effects of topical sodium cromoglicate on itch and flare in human skin induced by intradermal histamine: a randomised double-blind vehicle controlled intra-subject design trial

    OpenAIRE

    Stevens Michael T; Church Martin K; Edwards Alan M

    2011-01-01

    Abstract Background Itch is a prominent feature of many skin diseases, particularly atopic dermatitis and cutaneous mastocytosis. Sodium cromoglicate (SCG), a chromone developed for the treatment of allergic disease has been shown to reduce the severity of itch when applied topically to subjects with atopic dermatitis. The aim of this study was to investigate whether topical sodium cromoglicate can reduce the severity of itch induced by intradermal histamine. Methods SCG was introduced into t...

  4. Synthesis of Benzo[a]naphtho[2,3-c]xanthones from 2-styrylchromones

    OpenAIRE

    Tomé, Sara; Patoilo, Diana; Santos, Clementina M.M.; Silva, Artur

    2012-01-01

    2-Styrylchromones, a small group of natural occurring chromones vinylogues of flavones (2-phenylchromones) have been ex tensively studied (both by synthesis and transformations)111 due to their known important biological activities. 121 Following our interest in 2-styrylchromones and exploiting its reactivity as synthons in the preparation of other type of compounds, we studied their reactivity as dienophile in the Diels-Alder reaction with ortho-benzoquinodimethanesY1 Another ...

  5. 2-Styrylchromones: novel strong scavengers of reactive oxygen and nitrogen species

    OpenAIRE

    Gomes, Ana; Fernandes, Eduarda; Silva, Artur; Pinto, Diana; Santos, Clementina M.M.; Cavaleiro, José; Lima, José Costa

    2007-01-01

    http://apps.isiknowledge.com/full_record.do?product=UA&search_mode=GeneralSearch&qid=1&SID=S2NjaL1GBbk143plPl1&page=1&doc=1&colname=WOS 2-Styrylchromones are a small group of naturally occurring chromones, vinylogues of flavones (2-phenylchromones). Natural and synthetic 2-styrylchromones have been tested in different biological systems, showing activities with potential therapeutic applications. In particular, the potential and hitherto understudied antioxidant behavior of these com...

  6. Inhibition of NF-kB activation and cytokines production in THP-1 monocytes by 2-styrylchromones

    OpenAIRE

    Gomes, Ana; Capela, João Paulo; Ribeiro, Daniela; Freitas, Marisa; Silva, Artur; Pinto, Diana; Santos, Clementina M.M.; Cavaleiro, José; Lima, José L. F. C.; Fernandes, Eduarda

    2015-01-01

    Nuclear factor kappa B (NF-kB) is one of the most important transcription factors whose modulation triggers a cascade of signaling events, namely the expression of many cytokines, enzymes, chemokines, and adhesion molecules, some of which being potential key targets for intervention in the treatment of inflammatory conditions. The 2-styrylchromones (2-SC) designation represents a well-recognized group of natural and synthetic chromones, vinylogues of flavones (2-phenylchromones). Several 2-SC...

  7. Compounds identified on hexane and dichloromethane extracts of Salicornia ramosissima

    OpenAIRE

    Isca, Vera M. S.; Seca, Ana M. L.; Pinto, Diana C. G. A.; Artur M. S. Silva; Silva, Helena

    2012-01-01

    Salicornia ramosissima J. Woods (common purple glasswort) is an annual halophyte, widely distributed in the salt marsh of Ria de Aveiro (Portugal), that belongs to the Salicornia L. genus (Chenopodiaceae).[4] Although phytochemical studies genus on this genus report the presence of compounds which are well-recognized for their biological activities, such as flavonoids, chromones and alkaloids,[3] too little is known about secondary metabolites on purple glasswort. In our previous work we were...

  8. Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction.

    Science.gov (United States)

    Danda, Adithi; Kesava-Reddy, Naredla; Golz, Christopher; Strohmann, Carsten; Kumar, Kamal

    2016-06-01

    The catalytic addition of the amino acid derived bifunctional N-acylaminophosphine to an α-substituted allene ester generated a zwitterionic dipole that engaged the vinylogous ester function of 3-cyano-chromones in a [4 + 2] annulation reaction to deliver tetrahydroxanthones embodying three consecutive chiral centers in high yields and with excellent enantioselectivities. The established asymmetric synthesis further paves the way to two different classes of complex, sp(3)-rich tetracyclic benzopyrans via efficient cascade reactions. PMID:27187586

  9. [Therapy of allergic rhinitis].

    Science.gov (United States)

    Klimek, Ludger; Sperl, Annette

    2016-03-01

    If the avoidance of the provoking allergen is insufficient or not possible, medical treatment can be tried. Therapeutics of the first choice for the treatment of the seasonal and persistent allergic rhinitis are antihistamines and topical glucocorticoids. Chromones are less effective so they should only be used for adults with a special indication, for example during pregnancy. Beside the avoidance of the allergen the immunotherapy is the only causal treatment of allergic diseases. PMID:27120870

  10. Polyphenols from Eriosema tuberosum.

    Science.gov (United States)

    Ma, W G; Fuzzati, N; Li, Q S; Yang, C R; Stoeckli-Evans, H; Hostettmann, K

    1995-07-01

    A dichloromethane extract of the roots of Eriosema tuberosum exhibited antifungal activity against Cladosporium cucumerinum and Candida albicans using TLC bioautography. Bioassay-directed fractionation led to the isolation of four new compounds, eriosemaones A-D, together with a known compound, flemichin-D, as the active constituents. Three inactive polyphenols were also isolated after methylation, together with one new chromone, eriosematin. Structures were determined by spectroscopic analysis and from chemical evidence. PMID:7662271

  11. Antifungal methylphenone derivatives and 5-methylcoumarins from Mutisia friesiana.

    Science.gov (United States)

    Viturro, Carmen I; de la Fuente, Juana R; Maier, Marta S

    2003-01-01

    In addition to the known mutisicoumarin A, the aerial parts of the shrub Mutisia friesiana afforded five new methylphenones, two new 5-methylcoumarins and a new related chromone. Their structures were elucidated by spectroscopic methods 13C NMR data for mutisicoumarin A are reported for the first time. Mutisiphenones A and B and mutisicoumarin A showed antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum. PMID:12939040

  12. Studies on the antioxidant activity of some chromonylrhodanine derivatives.

    Science.gov (United States)

    Kruk, Irena; Piechowska, Teresa; Berczyński, Paweł; Kładna, Aleksandra; Bozdağ-Dündar, Oya; Ceylan-Unlusoy, Meltem; Aboul-Enein, Hassan Y

    2015-08-01

    Fifteen chromonylrhodamine derivatives (CRs) were synthesized and the antioxidant activity levels were evaluated for the first time. The antioxidant activity potencies of these chromone derivatives were evaluated towards superoxide anion radicals, hydroxyl radicals and 2,2-diphenyl-1-picrylhydrazyl radicals. Also, the total antioxidant capacity of the tested compounds was measured using the ferric-ferrozine assay. The antioxidant activities were investigated using a chemiluminescence (CL) assay, spectrophotometry measurements, direct electron paramagnetic resonance (EPR) and the EPR spin-trapping technique. The 5,5-dimethyl- 1-pyrroline-1-oxide (DMPO) was applied as spin trap. Eleven of the 15 chromone compounds exhibited a decrease in the CL accompanying the superoxide anion radical produced in anhydrous dimethylsulfoxide (DMSO), ranging from 71-94% at concentration of 1 mmol /L; four of these compounds enhanced light emission in the range 231-672%. Similarly, these compounds caused 28-58% inhibition in the intensity of the DMPO-OOH radical EPR signal and the DMPO-OH radical (from 12-48%). Furthermore, three of these compounds showed very good antioxidant response towards the DPPH radical (EC50 : 0.51-0.56 µmol/L) and the high reduction potentials. These findings demonstrate that the chromone compounds tested may be considered as effective free radicals scavengers, a finding that is of great pharmacological importance. PMID:25377006

  13. ラット腹腔肥満細胞からのアナフィラキシー性histamine遊離に対するdisodium cromoglycate, 6, 7-dihydro-6, 8, 8, 10-tetramethyl-8H-pyrano[3, 2-G]chromon-2-carboxylic acid(EAA)およびtranilastの抑制効果 -細胞外Ca(2+)の影響および交叉タキフィラキシーの成立-

    OpenAIRE

    池田, 滋樹

    1987-01-01

    To clarify the modes of the inhibitory action of DSCG, EAA and tranilast on histamine release, the effects of these drugs were studied on anaphylactic histamine release from rat peritoneal mast cells passively sensitized with mouse anti-ovalbumin serum. DSCG had a potent and dose-dependent inhibitory effect on the release in ordinary Hanks' medium, whereas its activity was far weaker in the absence of Ca(2+). No marked differences were observed in the inhibitory activities of EAA and tranilas...

  14. Synthesis, docking study and relaxant effect of 2-alkyl and 2-naphthylchromones on rat aorta and guinea-pig trachea through phosphodiesterase inhibition.

    Science.gov (United States)

    Rodríguez-Ramos, Fernando; Navarrete, Andrés; González-Andrade, Martín; Alarcón, Carlos; Aguilera-Cruz, Alejandro; Reyes-Ramírez, Adelfo

    2013-10-01

    Chromone (4), which form the base structure of various flavonoids isolated as natural products, is capable of relaxing smooth muscle. This is relevant to the treatment of high blood pressure, asthma and chronic obstructive pulmonary disease. The former disorder involves the contraction of vascular smooth muscle (VSM), and the latter two bronchoconstriction of airway smooth muscle (ASM). One of the principal mechanisms by which flavonoids relax muscle tissue is the inhibition of phosphodiesterases (PDEs), present in both VSM and ASM. Therefore, a study was designed to analyze the structure-activity relationship of chromone derivatives in vaso- and bronchorelaxation through the inhibition of PDE. Docking studies showed that these chromones bind at the catalytic site of PDEs. Consequently, we synthesized analogs of chromones substituted at position C-2 with alkyl and naphthyl groups. These compounds were synthesized from 2-hydroxyacetophenone and acyl chlorides in the presence of DBU and pyridine, modifying the methodology reported for the synthesis of 3-acylchromones by changing the reaction temperature from 80 to 30°C and using methylene chloride as solvent, yielding the corresponding phenolic esters 10a-10h. These compounds were cyclized with an equivalent of DBU, pyridine as solvent, and heated at reflux temperature, yielding the chromones 11a-11h. Evaluation of the vasorelaxant effect of 4, 11a-11h on rat aorta demonstrated that potency decreases with branched alkyl groups. Whereas the EC50 of compound 11d (substituted by an n-hexyl group) was 8.64±0.39 μM, that of 11f (substituted by an isobutyl group) was 14.58±0.64 μM. Contrarily, the effectiveness of the compound is directly proportional to the length of the alkyl chain, as evidenced by the increase in maximal effect of compound 11c versus 11d (66% versus 100%) and 11e versus 11f (60% versus 96%). With an aromatic group like naphthyl as the C-2 substituent, the effectiveness was only 43%. All compounds

  15. Brownian motion of particles in nematic fluids

    Science.gov (United States)

    Yao, Xuxia; Nayani, Karthik; Park, Jung; Srinivasarao, Mohan

    2011-03-01

    We studied the brownian motion of both charged and neutral polystyrene particles in two nematic fluids, a thermotropic liquid crystal, E7, and a lyotropic chromonic liquid crystal, Sunset Yellow FCF (SSY). Homogeneous planar alignment of E7 was easliy achieved by using rubbed polyimide film coated on the glass. For SSY planar mondomain, we used the capillary method recently developed in our lab. By tracking a single particle, the direction dependent diffussion coefficients and Stokes drag were measured in the nematic phase and isotropic phase for both systems.

  16. Synthesis and Antibacterial Screening of Novel Fluorine Containing Heterocycles

    Directory of Open Access Journals (Sweden)

    B K Karale

    2015-03-01

    Full Text Available A Claisen-Schimidt condensation of 2-hydroxyacetophenones 1a-f with an aldehyde 2 yielded a series of compounds 3a-f. Compounds 3a-f were transformed into series of substituted chromones 4a-f, pyrazolines 5a-f and aurones 6a-f on treatment with DMSO/ I2, NH2NH2 / EtOH and Hg(OAc2 / pyridine respectively. All these novel compounds were characterized by spectral techniques. All the compounds were screened for their antibacterial potential.

  17. Synthesis of new series of 3-hydroxy/acetoxy-2-phenyl-4-chromen-4-ones and their biological importance

    Indian Academy of Sciences (India)

    Mangesh Gharpure; Ratiram Choudhary; Vishwas Ingle; Harjeet Juneja

    2013-05-01

    3-Hydroxy-2-aryl/heteroaryl-4-chromones 4(a-n) were synthesized from appropriate chalcones 3(a-n) and acetylated to afford the corresponding acetoxy derivatives 5(a-n). All compounds were evaluated for antimicrobial activity against Staphylococus aureus, Bacillus subtillis, Escherichia coli and Pseudomonas aeruginosa as well as fungi e.g., Candida albicans and Aspergius niger. Inhibition caused by hydroxy flavones was relatively low, whereas that of their acetoxy ester analogues was substantially high. Structure of 6-chloro-2-(furan-2-yl)-4-oxo-4-chromen-3-yl acetate (5j) was also supported by means of single crystal X-ray diffraction.

  18. Reactions of 3-Formylchromone with Active Methylene and Methyl Compounds and Some Subsequent Reactions of the Resulting Condensation Products

    Directory of Open Access Journals (Sweden)

    M. Lácova

    2005-08-01

    Full Text Available This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc. The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based on the ability of the γ-pyrone ring to be opened by the nucleophilic attack is also reviewed. Finally, the applications of microwave irradiation as an unconventional method of reaction activation in the synthesis of condensation products is described and the biological activity of some chromone derivatives is noted.

  19. Reactions of 3-formylchromone with active methylene and methyl compounds and some subsequent reactions of the resulting condensation products.

    Science.gov (United States)

    Gasparová, Renata; Lácová, Margita

    2005-01-01

    This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc. The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based on the ability of the gamma-pyrone ring to be opened by the nucleophilic attack is also reviewed. Finally, the applications of microwave irradiation as an unconventional method of reaction activation in the synthesis of condensation products is described and the biological activity of some chromone derivatives is noted. PMID:18007363

  20. Dicty_cDB: Contig-U09816-1 [Dicty_cDB

    Lifescience Database Archive (English)

    Full Text Available M97514 ) Saccharomyces douglasii mitochondrial cytochrome c ... 32 0.45 6 ( AE014824 ) Plasmodium falciparum 3D7 chromo...ne) Mus musculus 10 days neonate skin ... 35 4.1 AE016879_2470( AE016879 |pid:none) Bacillus anthracis str. ...44( AE016853 |pid:none) Pseudomonas syringae pv. tomato... 34 9.2 CP001399_90( CP001399 |pid:none) Sulfolobus islan... malaccensis strain MP75 mitochondrion... 42 3e-04 5 ( AF063866 ) Melanoplus sanguinipes entomo.... 36 0.071 10 ( AL929354 ) Plasmodium falciparum strain 3D7, chromosome 5, s... 32 0.071 16 ( AP009180 ) Candidat

  1. Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition.

    Science.gov (United States)

    Korenaga, Toshinobu; Hayashi, Keigo; Akaki, Yusuke; Maenishi, Ryota; Sakai, Takashi

    2011-04-15

    An efficient synthesis of bioactive chiral flavanones (1) was achieved through the Rh-catalyzed asymmetric 1,4-addition of arylboronic acid to chromone. The reaction in toluene proceeded smoothly at room temperature in the presence of 0.5% Rh catalyst with electron-poor chiral diphosphine MeO-F(12)-BIPHEP. In this reaction, the 1,2-addition to (S)-1 frequently occurred to yield (2S,4R)-2,4-diaryl-4-chromanol as a byproduct, which could be reduced by changing the reaction solvent to CH(2)Cl(2) to deactivate the Rh catalyst (3% required). PMID:21413690

  2. Aloesin as a medical food ingredient for systemic oxidativestress of diabetes

    Institute of Scientific and Technical Information of China (English)

    2015-01-01

    Diabetes is a chronic disease that requires a long termmanagement where oxidative stress plays a pivotalrole in disease progression and intensifying secondarycomplications. In spite of all the research on diabetesand recent advances in diabetes treatments, the realityis that there is no cure for diabetes and its devastatingcomplications. While currently available anti-diabetictherapies are effective in reducing blood glucose level,they are not without associated side effects whenthey are used for a long term applications. As a result,physicians and patients are inclining more towards to asafer therapy with less serious side effects in the formof medicinal foods and botanical alternatives that aresuitable for chronic usage. Aloesin, an Aloe chromone,has previously been formulated with an aloe polysaccharideto give a composition called Loesyn, whereit showed significant impact in reducing glycosylatedhemoglobin, fasting blood glucose, fructosamine andplasma insulin level in humans. Radical scavengingactivities of chromones and polysaccharides fromAloe have also been reported. Here we rationalize therelevance of use of Aloesin alone or in a standardizedblend with Aloe polysaccharides, as a potential medicalfood to manage systemic oxidative stress and/or highblood glucose of diabetes.

  3. Crystal structure of 4-oxo-4H-chromene-3-carb-oxy-lic acid.

    Science.gov (United States)

    Ishikawa, Yoshinobu

    2015-08-01

    In the title compound, C10H6O4, also known as 3-carb-oxy-chromone, the non-H atoms of the chromone ring are essentially coplanar (r.m.s. deviation = 0.0057 Å), with the maximum deviation from their least-squares plane [0.011 (2) Å] being for a pyran C atom. The dihedral angle between the fused ring and plane of the carb-oxy group is 3.06 (2)°. An intra-molecular hydrogen bond is formed between the ring carbonyl O atom and the carb-oxy O-H atom, closing an S(6) loop. In the crystal, mol-ecules are assembled by stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.844 (3) Å] and C-H⋯O hydrogen bonds, generating a three-dimensional network. Short contacts are also observed between the carb-oxy O and C atoms [C=O⋯C=O = 3.002 (3) Å]. PMID:26396807

  4. Characterization of perylene diimide dye self-assemblies and their use as templates for the synthesis of hybrid and supermicroporous nanotubules.

    Science.gov (United States)

    Rodríguez-Abreu, Carlos; Aubery-Torres, Carolina; Solans, Conxita; López-Quintela, Arturo; Tiddy, Gordon J T

    2011-10-01

    The self-organizing structures formed by a water-soluble perylene diimide dye (PDI) have been studied by several experimental techniques as potential templates for the preparation of hybrid nanomaterials. The dye forms chromonic-nematic and hexagonal liquid crystals in water. The aggregates in liquid crystals consist of one-molecule-wide stacks. From the changes in the solution proton NMR chemical shifts with concentration, it appears that adjacent molecules are twisted. There is significant broadening of the aromatic resonances at higher concentrations, arising from nonmotionally averaged dipole-dipole coupling between adjacent aromatic hydrogens. This is attributed to slow overall rotation of the aggregates in solution, suggesting that they grow up to several tens of nanometers. Dye aggregates serve as templates for the formation of silica tubules (1-5 μm length, average diameter ≈300 nm), with aligned and very thin (1-2 nm) dye nanostripes embedded in the walls. The silica tubes precipitated from solution are formed by the cooperative interaction between PDI and silica species during the sol-gel reaction. Upon calcination, silica nanotubules with supermicroporous walls are obtained. In comparison with conventional surfactant systems, the use of π-π stacked chromonic aggregates brings new possibilities for the templated fabrication of pores with sizes below the mesoporous range. Materials could find applications in photovoltaics as well as in shape selective catalysis and adsorption. PMID:21942535

  5. Eco-friendly synthesis and potent antifungal activity of 2-substituted coumaran-3-ones

    Directory of Open Access Journals (Sweden)

    PRABHA SOLANKI

    2012-11-01

    Full Text Available Solanki P, Shekhawat P. 2012. Eco-friendly synthesis and potent antifungal activity of 2-substituted coumaran-3-ones. Nusantara Bioscience 4: 101-104. 3-halochromones (IIa-c and IIIa-c have been synthesized by treating 1- (2-hydroxyphenyl-3-methyl-1,3-propanediones (Ia-c with bromine or sulphuryl chloride in dioxane respectively. These chromones were employed in the synthesis of 2-acetyl-coumaran-3-ones (IVa-f. These were subjected to Knoevenagel condensation to give 2-cinnamoyl coumaran-3-ones. In vitro assay and field trials of these compounds against Fusarium oxysporum were carried out to study the antifungal effect of target compounds. Compound Va was the most effective growth inhibitor of the pathogen, whereas Vc showd a little tendency and Vb, Vd, Ve and Vf hardly inhibits the growth

  6. Expansion 5-6 of heterocyclic compounds by Stork-De Selms method; Expansion 5-6 de compuestos heterociclicos por el metodo de Stork-De Selms

    Energy Technology Data Exchange (ETDEWEB)

    Albores, Marta E.; Maldonado, Luis A. [Universidad Nacional Autonoma de Mexico, Mexico, D.F. (Mexico)

    1999-08-01

    The construction of the chromone, thiochromone and 4-quinolone ring systems by ring expansion of appropriate 5-membered heterocyclic enol acetates, with dibromocarbene generated by Seyferth's method, is described. The use of the method for the synthesis of 2-bromo-1-naphthyl acetate and an attempted synthesis of the flavone ring are also reported. [Spanish] Se describe la construccion de los sistemas anulares de cromona, tiocromona y 4-quinolona por la expansion de acetatos de enol heterociclicos apropiados, con dibromocarbeno generado por el metodo de Seyferth. Tambien se informa del uso de este metodo para la sintesis del acetato de 2-bromo-1-naftilo y del intento de sintesis del anillo de flavona.

  7. Energetics of flavone and flavanone

    Energy Technology Data Exchange (ETDEWEB)

    Sousa, Clara C.S. [Centro de Investigacao em Quimica, Departamento de Quimica, Faculdade de Ciencias da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto (Portugal); Matos, M. Agostinha R. [Centro de Investigacao em Quimica, Departamento de Quimica, Faculdade de Ciencias da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto (Portugal)], E-mail: marmatos@fc.up.pt; Morais, Victor M.F. [Centro de Investigacao em Quimica, Departamento de Quimica, Faculdade de Ciencias da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto (Portugal); Instituto de Ciencias Biomedicas Abel Salazar, ICBAS, Universidade do Porto, P-4099-003 Porto (Portugal)

    2009-12-15

    In this work, we have determined the experimental standard (p{sup o} = 0.1 MPa) molar enthalpies of formation, in gas phase, of flavone and flavanone. These results were obtained by combining the standard molar enthalpies of formation in the condensed phase with the standard molar enthalpies of sublimation. The former values were derived from combustion experiments in oxygen, at T = 298.15 K, in a static bomb calorimeter. The values of the standard molar enthalpies of sublimation were obtained by Calvet microcalorimetry and corrected to T = 298.15 K. High-level density functional theory calculations using the B3LYP hybrid exchange-correlation energy functional with extended basis sets and more accurate correlated computational techniques of the MCCM/3 suite have been performed for the compounds. The obtained results, experimental and computational, for flavone and flavanone were compared with those obtained for chromone and chromanone, respectively.

  8. Desorption Electrospray Ionization (DESI Mass Spectrometric Imaging of the Distribution of Rohitukine in the Seedling of Dysoxylum binectariferum Hook. F.

    Directory of Open Access Journals (Sweden)

    Patel Mohana Kumara

    Full Text Available Ambient ionization mass spectrometric imaging of all parts of the seedling of Dysoxylum binectariferum Hook. f (Meliaceae was performed to reconstruct the molecular distribution of rohitukine (Rh and related compounds. The species accumulates Rh, a prominent chromone alkaloid, in its seeds, fruits, and stem bark. Rh possesses anti-inflammatory, anti-cancer, and immuno-modulatory properties. Desorption electrospray ionization mass spectrometry imaging (DESI MSI and electrospray ionization (ESI tandem mass spectrometry (MS/MS analysis detected Rh as well as its glycosylated, acetylated, oxidized, and methoxylated analogues. Rh was predominantly distributed in the main roots, collar region of the stem, and young leaves. In the stem and roots, Rh was primarily restricted to the cortex region. The identities of the metabolites were assigned based on both the fragmentation patterns and exact mass analyses. We discuss these results, with specific reference to the possible pathways of Rh biosynthesis and translocation during seedling development in D. binectariferum.

  9. Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica.

    Science.gov (United States)

    Fujioka, T; Furumi, K; Fujii, H; Okabe, H; Mihashi, K; Nakano, Y; Matsunaga, H; Katano, M; Mori, M

    1999-01-01

    The CHCl3 extract of the root of Angelica japonica showed high inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth. From this extract, a new furanocoumarin named japoangelone and four furanocoumarin ethers of falcarindiol, named japoangelols A-D, were isolated together with caffeic acid methyl ester, four polyacetylenic compounds (panaxynol, falcarindiol, 8-O-acetylfalcarindiol, and (9Z)-1,9-heptadecadiene-4,6-diyne-3,8,11-triol), eight coumarins (osthol, isoimperatorin, scopoletin, byakangelicin, xanthotoxin, bergapten, oxypeucedanin methanolate, and oxypeucedanin hydrate), and two chromones (3'-O-acetylhamaudol, and hamaudol). The structures of the new isolates were determined based on spectral evidence. The ED50 of isolates against MK-1, HeLa, and B16F10 cell lines are reported. PMID:9987830

  10. Characterization and Determination of 2-(2-Phenylethylchromones in Agarwood by GC-MS

    Directory of Open Access Journals (Sweden)

    Hao-Fu Dai

    2013-10-01

    Full Text Available Agarwood is the fragrant resinous heartwood obtained from certain trees in the genus Aquilaria belonging to the family Thymelaeaceae. 2-(2-Phenylethylchromones and characteristic sesquiterpenes are the main classes of aromatic compounds isolated from agarwood. Although there are many sesquiterpenes, relatively few 2-(2-phenylethylchromones have been determined in agarwood by GC-MS. After analysis of the MS spectra of eighteen 2-(2-phenylethylchromone derivatives isolated from agarwood and identified by NMR spectroscopy, together with the reported MS data and characteristic of structures of 2-(2-phenylethylchromones, the MS characterization, fragmentation patterns and characteristic fragment peaks for the compounds were deduced and a table summarizing MS characterization of 2-(2-phenylethylchromones in agarwood is presented. All the 2-(2-phenylethylchromones previously reported in agarwood are substituted by methoxy or/and hydroxy groups, except for one compound. Due to the fact they all possess the same basic skeleton (molecular weight: 250 and similar substituent groups (methoxy or hydroxy groups, a formula (30m + 16n = MW − 250 is provided to calculate the number of methoxy (m or hydroxy (n groups according to molecular ion peak or molecular weight (MW. We deduced that the characteristic fragmentation behaviors of the 2-(2-phenylethylchromones are the cleavages of the CH2-CH2 bond between chromone moiety and phenyl moiety. Thus, characteristic fragment ions, such as m/z 91 [C7H7], 107 [C7H6+OH], 121 [C7H6+OCH3], 137 [C7H5+OH+OCH3] are formed by different substituted benzyl moieties, while characteristic fragment ions such as m/z 160 [C10H8O2], 176 [C10H7O2+OH], 190 [C10H7O2+OCH3], 220 [C10H6O2+OCH3×2] are formed by different substituted chromone moieties. Furthermore, rules regarding to the relationship between the positions of hydroxy or methoxy groups and the relative abundances of benzyl and chromone fragment ions have been deduced

  11. Study of root and leaf rachis of Spathelia excelsa: phytochemistry and activity against fungus Moniliophthora perniciosa associated with cupuassu (Theobroma grandiflorum); Estudo em raiz e raquis foliar de Spathelia excelsa: fitoquimica e atividade frente ao fungo Moniliophthora perniciosa associado ao cupuacuzeiro (Theobroma grandiflorum)

    Energy Technology Data Exchange (ETDEWEB)

    Carvalho, Loretta Ennes de; Lima, Maria da Paz; Maximo, Ariane da Costa; Pereira, Elaine Cristina da Silva; Moreira, Wagner Alan dos Santos [Instituto Nacional de Pesquisas da Amazonia (INPA), Manaus, AM (Brazil). Coordenacao de Pesquisas em Tecnologia e Inovacao; Ferreira, Antonio Gilberto [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Veras, Solange de Mello [Universidade Federal do Amazonas (UFAM), Manaus, AM (Brazil). Fac. de Ciencias Agrarias; Souza, Maria Geralda de, E-mail: mdapaz@inpa.gov.br [Empresa Brasileira de Pesquisa Agropecuaria (EMBRAPA), Manaus, AM (Brazil)

    2012-07-01

    The chemical composition of Spathelia excelsa (Krause) R. S. Cowan and Brizicky was investigated and the limonoids harrisonin (1) and deacetylspathelin (2), alkaloids folinin and casimiroin mixture (3a,b), plus a further casimiroin (3b) were identified in methanol extract from root. The CH{sub 2}Cl{sub 2} extract from the rachis yielded protolimonoid 3{beta}-angeloyl-21,24-epoxy-7{alpha},21{alpha},23{alpha},25-tetrahydroxy-4{alpha},4{beta},8{beta},10{beta}-tetramethyl -25-dimethyl-14,18-cyclo-5{alpha},13{alpha},14{alpha},17{alpha}-cholestane (4), and methanol extract, the limonoids limonin diosphenol (5) and perforatin (6), as well as the chromone biflorin (7). Harrisonin and biflorin were isolated for the first time in this genus. On the antifungal assay against witches' broom (Moniliophthora perniciosa) compound 3b was found to be active. (author)

  12. Chemical constituents from the roots of Spathelia excelsa and their antiprotozoal activity

    Energy Technology Data Exchange (ETDEWEB)

    Moreira, Wagner A. dos Santos; Lima, Maria da Paz [Instituto Nacional de Pesquisas da Amazonia (IMPA), Manaus, AM (Brazil). Coordenacao de Pesquisas em Produtos Naturais], e-mail: mdapaz@inpa.gov.br; Ferreira, Antonio Gilberto [Universidade Federal de Sao Carlos (UFSCar), SP (Brazil). Dept. de Quimica; Ferreira, Izabel C. Piloto; Nakamura, Celso V. [Universidade Estadual de Maringa (UEM), PR (Brazil). Dept. de Analises Clinicas

    2009-07-01

    Phytochemical investigation from roots of Spathelia excelsa yielded the chromones 10(2,3-epoxy-3-methylbutanyl) spatheliachromen and 10(2,3-dihydroxy-3-methylbutanyl) methoxyspatheliacromen (5-methoxyspatheliabischromen); limonoid deacetylspathelin and protolimonoid C-21-epimers 3{beta}-angeloyloxy-7a,24,25-trihydroxy-21,23-oxide-14,18-cycloapotirucall -21-hemiacetal; the alkaloids 7,8-dimethoxyflindersin, casimiroin and N-methyl-4,7,8-trimethoxyquinolin-2(1H)-one, besides a mixture of {beta}-sitosterol and stigmasterol. Assays on promastigote forms of Leishmania braziliensis, deacetylspathelin showed moderate activity; and on epimastigote forms of Trypanossoma cruzi, 10(2,3-epoxy-3-methylbutanyl)spatheliachromen exhibited strong activity (IC50 = 11 {mu}g mL-1). (author)

  13. Structural Characterization and Identification of Major Constituents in Jitai Tablets by High-Performance Liquid Chromatography/Diode-Array Detection Coupled with Electrospray Ionization Tandem Mass Spectrometry

    Directory of Open Access Journals (Sweden)

    Weidong Zhang

    2012-09-01

    Full Text Available In the present study a universally applicable HPLC-DAD/ESI-MS/MS method was developed for carrying out the comprehensive characterization of Jitai tablets (JTT. Based on the ESI-MSn fragmentation patterns of the reference standards, a total of 101 components were identified or tentatively characterized by comparing their retention times, UV and MS spectra with those of reference standards or through the matching of empirical information with those of published components in the in-house library. The characteristic fragmentation pattern of alkaloids, phenolic acids, tanshinones, flavonoid glycosides, cyanogenic glycosides, ginsenosides, 2-(2-phenylethyl chromones, phthalides and gingerol-related compounds were tentatively elucidated using structurally-relevant product ions. It was observed that neutral losses of C9H10O3 and C9H8O2 were the characteristic product ions of scopola alkaloids. Neutral fragment mandelonitrile was the characteristic ion of cyanogenic glycosides. To our knowledge, tropylium ion and C4H2O unit were the characteristic ions of 2-(2-phenylethyl chromone, which resulted from the Retro-Diels-Alder (RDA cleavage of the C ring. The results indicated that the developed analysis method could be employed as a rapid, effective technique for structural characterization of chemical constituents in TCM. This work is expected to provide comprehensive information for the quality evaluation and pharmacokinetic studies of JTT.

  14. New insights in the discovery of novel h-MAO-B inhibitors: structural characterization of a series of N-phenyl-4-oxo-4H-chromene-3-carboxamide derivatives

    Directory of Open Access Journals (Sweden)

    Ligia R. Gomes

    2015-05-01

    Full Text Available Six N-substituted-phenyl 4-oxo-4H-chromene-3-carboxamides, namely N-(2-nitrophenyl-4-oxo-4H-chromene-3-carboxamide, C16H10N2O5 (2b, N-(3-methoxyphenyl-4-oxo-4H-chromene-3-carboxamide, C17H13NO4, (3a, N-(3-bromophenyl-4-oxo-4H-chromene-3-carboxamide, C16H10BrNO3, (3b, N-(4-methoxyphenyl-4-oxo-4H-chromene-3-carboxamide, C17H13NO4, (4a, N-(4-methylphenyl-4-oxo-4H-chromene-3-carboxamide, C17H13NO3, (4d, and N-(4-hydroxyphenyl-4-oxo-4H-chromene-3-carboxamide, C16H11NO4, (4e, have been structurally characterized. All compounds exhibit an anti conformation with respect to the C—N rotamer of the amide and a trans-related conformation with the carbonyl groups of the chromone ring of the amide. These structures present an intramolecular hydrogen-bonded network comprising an N—H...O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an S(6 ring, and a weak Car—H...O hydrogen bond in which the carbonyl group of the amide acts as acceptor for the H atom of an ortho-C atom of the exocyclic phenyl ring, which results in another S(6 ring. The N—H...O intramolecular hydrogen bond constrains the carboxamide moiety such that it is virtually coplanar with the chromone ring.

  15. Synthesis and Antihistaminic Activity of Diarylmethylpiperazine Derivatives%二芳甲基哌嗪衍生物合成及其抗组胺活性的研究

    Institute of Scientific and Technical Information of China (English)

    邓娜; 尹卓; 汪濛

    2011-01-01

    Objective The diarylmethylpiperazine moiety as active group frequently existing in the structures of H1 receptor antagonists and chromone-2-carboxylic acid moiety as active structure existing in leukotriene receptor antagonists were spliced on the basis of isostere and mosaic theory, and a series of diarylmethylpiperazine derivatives were synthesized and their antihistaminic activities were explored. Methods The lydroxyl-substituted chromone2-carboxylic ester contained an aliphatic chain-linked to diarylmetlylpiperazine to produce diarylmethylpiperazine derivatives. The antihistaminic activities of diarylmethylpiperazine derivatives were measured. Results The structures of diarylmethylpiperazine derivatives were identified by MS and H NMR spectra.%目的 利用电子等排和拼合原理,选择H1受体拮抗剂的活性部分二芳甲基哌嗪与白三烯受体拮抗剂的活性结构色酮-2-羧酸拼接,设计合成二芳甲基哌嗪衍生物,并且考察其抗组胺活性.方法 以羟基取代的色酮-2-羧酸酯为母体,将羟基与二芳甲基哌嗪通过脂肪链相连,得二芳甲基哌嗪衍生物,并测定化合物的抗组胺活性.结果 目标化合物的组成和结构经质谱和核磁共振氢谱确认.

  16. Quality Analysis of Eaglewood Induced by New Stimulation Technology%生物诱导法刺激白木香树干木质部产香的质量分析

    Institute of Scientific and Technical Information of China (English)

    张肖; 吴泽青; 林励; 李然

    2016-01-01

    Objective To evaluate the quality of different parts of agarwood formed by stimulation with biological induction method, thus to provide evidence for agarwood quality control. Methods The identification of agarwood and the determination of alcohol extracts from agarwood were achieved by the methods of Chinese Pharmacopeia. The determination of total chromones from agarwood was achieved by ultraviolet spectrophotometry(UVS), with aquilarone E as reference substance and 760 nm as the detective wavelength. Results The UVS method was stable within 5 h and the recovery rate was 95.71%(sR=2.09%). The average alcohol extract content of the outside part of the xylem of Aquilaria sinensis(Lour.) Gilg(part B) was 109.4 mg/g,which was higher than that (100 mg/g) of the Chinese Pharmacopoeia standard. The average content of total chromones was 15.73 mg/g. The rest identification results were accorded with the requirements of Chinese Pharmacopeia. The average alcohol extract content of the inside part of the xylem(part Z) was 47.6 mg/g, and the average content of total chromones was 2.66 mg/g. The rest identification results did not reach the requirements of Chinese Pharmacopeia. Conclusion The obtained part B of the agarwood meets the requirements of Chinese Pharmacopeia, while part Z has color changed and its quality has not yet reached the requirements. The results indicated that the biological induction method impacts Aquilaria sinensis xylem from outside to inside, and then the xylem grows into agarwood gradually.%【目的】考察生物诱导法刺激白木香后不同部位所产沉香的质量,为评价沉香质量提供实验依据。【方法】采用中国药典沉香项下方法进行药材鉴别和醇浸出物含量测定;采用可见分光光度法(VS)以磷钨酸钼—硫酸锂为显色剂,以Aquilarone E色酮作为对照品溶液,在760 nm波长下测定沉香药材中沉香总色酮含量。【结果】本研究所使

  17. Lipophilic Constituents of Rumex vesicarius L. and Rumex dentatus L.

    Directory of Open Access Journals (Sweden)

    Mona A. Abou Elfotoh

    2013-09-01

    Full Text Available Rumex dentatus L. and Rumex vesicarius L., of the family Polygonaceae, are edible herbs growing wild in Egypt. Their lipoid constituents were examined by both liquid chromatography/mass spectrometry (LC/MS and by gas chromatography/mass spectrometry (GC/MS. Their essential oil compositions consisted mainly of thujene, limonene, fenchon, estragole, and anethole but at largely different concentration. Fatty acid compositions were similar among the two species and consisting of palmitic, oleic, linoleic and linolenic acids, with R. vesicarius containing much higher level of omega-3-fatty acids. Both of the crude lipid extracts of the two species showed strong antioxidant activity as a radical quenching agent against 2,2-diphenyl-1-picrylhydrazyl (DPPH systems. Antioxidant activities were mostly associated with the polar lipid fractions. High performance thin layer chromatography (HPTLC, both in the normal and reversed phase,as well as liquid chromatography/mass spectrometry (LC/MS in the positive and negative electrospray ionization (ESI, showed unique chemical profile for each species that can be useful for species identification and quality control of herbal drug formulations. R. vesicarius was characterized by abundances of flavonoids and R. dentatus was abundant in anthraquinones and chromones.

  18. Los compuestos fenólicos en la autodefensa de los vegetales

    Directory of Open Access Journals (Sweden)

    Maestro-Durán, R.

    1993-12-01

    Full Text Available This article covers the studies on phytoalexins activity of phenolic compounds (cinnamic acids, flavonoids, isoflavonoids, deoxianthocyanins, stilbenes, coumarins, chromones against fungi and bacteria. The relationship between hydrophilic-lipophilic balance activity is reported. Finally some reports on the preparation of synthetic phytoalexins sharing structural similarities with the natural ones (stilbenes, epi-catechin derivatives, of commercial interest as pesticides, insecticides and fungicides, are revised.

    En este trabajo se recogen los estudios sobre la actividad como fitoalexinas (compuestos post-infeccionales cuya formación implica o desrrepresión de genes o activación de un sistema enzimático que no operaba antes de la infección, tanto frente a hongos como frente a bacterias, de compuestos de tipo fenólico (ácidos cinámicos, flavonoides, isoflavonoides, deoxiantocianinas, estilbenos, cumarinas, cromonas. Se señala la relación entre el balance hidrófilo-lipófilo y la actividad como fitoalexinas. Finalmente se recogen trabajos sobre la obtención de fitoalexinas sintéticas de estructuras similares a las naturales (estilbenos, derivados de epicatequinas de interés comercial como pesticidas, insecticidas o fungicidas.

  19. Secondary Metabolites of the Endophytic Fungus Lachnum abnorme from Ardisia cornudentata.

    Science.gov (United States)

    Chang, Hsun-Shuo; Lin, Chu-Hung; Chen, Yi-Shuan; Wang, Hui-Chun; Chan, Hing-Yuen; Hsieh, Sung-Yuan; Wu, Ho-Cheng; Cheng, Ming-Jen; Yuan, Gwo-Fang; Lin, Shan-Yu; Lin, Yue-Jin; Chen, Ih-Sheng

    2016-01-01

    Fractionation of an EtOAc-soluble fraction of the solid fermentate of an endophytic fungus, Lachnum abnorme Mont. BCRC 09F0006, derived from the endemic plant, Ardisia cornudentata Mez. (Myrsinaceae), resulted in the isolation of three new chromones, lachnochromonins D-F (1-3), one novel compound, lachabnormic acid (4), along with nine known compounds (5-13). Their structures were elucidated by spectroscopic analyses. Alternariol-3,9-dimethyl ether (6) was given the correct data as well as 2D spectral analyses for the first time. This is the first report of the isolation of one unprecedented compound 4 from Lachnum genus, while all known compounds were also found for the first time from Lachnum. The effects of some isolates (3, 4, 7-9, 10, and 13) on the inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophages were also evaluated. Several compounds exhibited weak inhibitory activity on lipopolysaccharide (LPS)-stimulated NO production in RAW 264.7 macrophages. PMID:27618025

  20. Chemical Composition of the Essential Oil and Diethyl Ether Extract of Trinia glauca (L.) Dumort. (Apiaceae) and the Chemotaxonomic Significance of 5-O-Methylvisamminol.

    Science.gov (United States)

    Radulović, Niko S; Đorđević, Miljana R; Dekić, Milan S; Blagojević, Polina D

    2016-04-01

    Analyses by GC, GC/MS, and NMR spectroscopy (1D- and 2D-experiments) of the essential oil and Et2 O extract of Trinia glauca (L.) Dumort. (Apiaceae) aerial parts allowed a successful identification of 220 constituents, in total. The major identified compounds of the essential oil were (Z)-falcarinol (10.6%), bicyclogermacrene (8.0%), germacrene D (7.4%), δ-cadinene (4.3%), and β-caryophyllene (3.2%), whereas (Z)-falcarinol (47.2%), nonacosane (7.4%), and 5-O-methylvisamminol (4.0%) were the dominant constituents of the extract of T. glauca. One significant difference between the compositions of the herein and the previously analyzed T. glauca essential oils (only two reports) was noted. (Z)-Falcarinol was the major constituent in our case, whereas germacrene D (14.4 and 19.6%) was the major component of the previously studied oils. Possible explanations for this discrepancy were discussed. 5-O-Methylvisamminol, a (furo)chromone identified in the extract of T. glauca, has a limited occurrence in the plant kingdom and is a possible excellent chemotaxonomic marker (family and/or subfamily level) for Apiaceae. PMID:26919331

  1. Anomalous swimming behavior of bacteria in nematic liquid crystals

    Science.gov (United States)

    Sokolov, Andrey; Zhou, Shuang; Lavrentovich, Oleg; Aranson, Igor

    2015-03-01

    Flagellated bacteria stop swimming in isotropic media of viscosity higher than 0.06kgm-1s-1. However, Bacillus Subtilis slows down by only about 30% in a nematic chromonic liquid crystal (CLC, 14wt% DSCG in water), where the anisotropic viscosity can be as high as 6kgm-1s-1. The bacteria velocity (Vb) is linear with the flagella rotation frequency. The phase velocity of the flagella Vf ~ 2Vb in LC, as compared to Vf ~ 10Vb in water. The flow generated by the bacteria is localized along the bacterial body axis, decaying slowly over tens of micrometers along, but rapidly over a few micrometers across this axis. The concentrated flow grants the bacteria new ability to carry cargo particles in LC, ability not seen in their habitat isotropic media. We attribute these anomalous features to the anisotropy of viscosity of the CLC, namely, the viscosities of splay and twist is hundreds times higher than that of bend deformation, which provides extra boost of swimming efficiency and enables the bacteria swim at considerable speed in a viscous medium. Our findings can potentially lead to applications such as particle transportation in microfluidic devices. A.S and I.A are supported by the US DOE, Office of Science, BES, Materials Science and Engineering Division. S.Z. and O.D.L are supported by NSF DMR 1104850, DMS-1434185.

  2. The effects of topical sodium cromoglicate on itch and flare in human skin induced by intradermal histamine: a randomised double-blind vehicle controlled intra-subject design trial

    Directory of Open Access Journals (Sweden)

    Stevens Michael T

    2011-03-01

    Full Text Available Abstract Background Itch is a prominent feature of many skin diseases, particularly atopic dermatitis and cutaneous mastocytosis. Sodium cromoglicate (SCG, a chromone developed for the treatment of allergic disease has been shown to reduce the severity of itch when applied topically to subjects with atopic dermatitis. The aim of this study was to investigate whether topical sodium cromoglicate can reduce the severity of itch induced by intradermal histamine. Methods SCG was introduced into the skin of healthy volunteers both by iontophoresis and by topical application using a new 4% cutaneous emulsion (Altoderm™. The skin was then challenged with intradermal histamine. Measurements were made of severity of itch, size of wheal and flare and change in blood flux Results SCG significantly reduced the severity of itch (P = 0.0045 and flare (P = 0.0143 when delivered by iontophoresis. SCG 4% cutaneous emulsion significantly reduced severity of itch (P = 0.024 and flare (P = 0.015 in atopic subjects. Trend analysis showed increasing effect on itch with increased concentrations of SCG, which was significant (P = 0.046. There were no effects on wheal or blood flux. Conclusions Topically applied SCG, administered in a new cutaneous emulsion base, significantly reduced the itch and flare caused by intradermal histamine. The effect was greatest in atopic subjects and increased with the concentration of SCG in the emulsion. Trial registration ISRCTN35671014

  3. Chemical profiling and anti-psoriatic activity of methanolic extract of Andrographis nallamalayana J.L.Ellis.

    Science.gov (United States)

    Parlapally, Sunitha; Cherukupalli, Neeraja; Bhumireddy, Sudarshana Reddy; Sripadi, Prabhakar; Anisetti, Ravindernath; Giri, Charu Chandra; Khareedu, Venkateswara Rao; Reddy Vudem, Dashavantha

    2016-06-01

    Andrographis nallamalayana is being widely used as tribal medicine in the treatment of leucoderma and mouth ulcers. Chemical profiling of methanolic extract of the whole plant (PE), using GC-MS and LC-MS, revealed the presence of compounds viz. α-tocopherol, β-sitosterol, tetradecanoic acid, monostearin, flavones/flavanones and their glycosides, chromones, etc. Topical application of imiquimod on the dorsal portion of male BALB/C mice resulted in the development of psoriatic symptoms (erythema, scaling, thickening and folding) with a mean disease activity index (DAI) of >7.0. Topical treatment with 100-μL PE (~6.4%/12.8%) formulations, for 12-days, resulted in the alleviation of disease symptoms. Compared to water-based formulations, emu oil-based formulation, PE400EO was found more effective in reducing the mean DAI (>84%), keratinocyte count (>65%) (p < 0.01) and interleukin-22 (~70%) (p < 0.05). We report, for the first time, anti-psoriatic activity of A. nallamalayana having great potential in developing a potent phytomedicine against psoriasis. PMID:26153074

  4. Determination of Isoflavone Content in SRM 3238 Using Liquid Chromatography-Particle Beam/Electron Ionization Mass Spectrometry.

    Science.gov (United States)

    Zhang, Lynn X; Burdette, Carolyn Q; Phillips, Melissa M; Rimmer, Catherine A; Marcus, R Kenneth

    2015-01-01

    The characterization of marker components in botanical materials is a challenging task, and the increased consumption of botanicals and dietary supplements demands a greater understanding of the associated health benefits and risks. In order to successfully acquire and compare clinical results and correlate health trends, accurate, precise, and validated methods of analysis must be developed. Presented here is the development of a quantitative method for the determination of soy isoflavones (daidzin, glycitin, genistin, daidzein, and genistein) using LC-particle beam/electron ionization-MS (LC-PB/EIMS). An internal standard (IS) approach for quantitation with 7-hydroxy-4- chromone as the IS compound was used, with response factors for each individual isoflavone obtained from calibrant solutions. The results from this method were compared with the certified and reference values for National Institute of Standards and Technology (NIST) SRM 3238 Soy-Containing Solid Oral Dosage Form to demonstrate that the method was in control. Results obtained using LC-PB/EIMS were consistent with the NIST certified or reference values and their uncertainties for all five isoflavones, demonstrating that the LC-PB/EIMS approach is both accurate and precise when used for the determination of the target isoflavones in soy-containing dietary supplement finished products while simultaneously providing structural information. PMID:26651559

  5. Retrieving the saddle-splay elastic constant K24 of nematic liquid crystals from an algebraic approach.

    Science.gov (United States)

    Fumeron, Sébastien; Moraes, Fernando; Pereira, Erms

    2016-09-01

    The physics of light interference experiments is well established for nematic liquid crystals. Using well-known techniques, it is possible to obtain important quantities, such as the differential scattering cross section and the saddl-splay elastic constant K24. However, the usual methods to retrieve the latter involve adjusting of computational parameters through visual comparisons between the experimental light interference pattern or a (2) H-NMR spectral pattern produced by an escaped-radial disclination, and their computational simulation counterparts. To avoid such comparisons, we develop an algebraic method for obtaining of saddle-splay elastic constant K24. Considering an escaped-radial disclination inside a capillary tube with radius R0 of tens of micrometers, we use a metric approach to study the propagation of the light (in the scalar wave approximation), near the surface of the tube and to determine the light interference pattern due to the defect. The latter is responsible for the existence of a well-defined interference peak associated to a unique angle [Formula: see text] . Since this angle depends on factors such as refractive indexes, curvature elastic constants, anchoring regime, surface anchoring strength and radius R0, the measurement of [Formula: see text] from the interference experiments involving two different radii allows us to algebraically retrieve K24. Our method allowed us to give the first reported estimation of K24 for the lyotropic chromonic liquid crystal Sunset Yellow FCF: K 24 = 2.1 pN. PMID:27589980

  6. A new class of hybrid anticancer agents inspired by the synergistic effects of curcumin and genistein: Design, synthesis, and anti-proliferative evaluation.

    Science.gov (United States)

    Chen, Qiao-Hong; Yu, Kevin; Zhang, Xiaojie; Chen, Guanglin; Hoover, Andrew; Leon, Francisco; Wang, Rubing; Subrahmanyam, Nithya; Addo Mekuria, Ermias; Harinantenaina Rakotondraibe, Liva

    2015-10-15

    Inspired by the synergistic effects of dietary natural products with different scaffolds on the inhibition of cancer cell proliferation, incorporation of central (1E,4E)-1,4-penta-dien-3-one linker (an optimal substitute for the central metabolically unstable diketone linker of curcumin), 1-alkyl-1H-imidazol-2-yl (a promising bioisostere of terminal aryl group in curcumin), and chromone (the common pharmacophore in genistein and quercetin) into one chemical entity resulted in ten new hybrid molecules, 3-((1E,4E)-5-(1-alkyl-1H-imidazol-2-yl)-3-oxopenta-1,4-dien-1-yl)-4H-chromen-4-ones. They were synthesized through a three-step transformation using acid-catalyzed aldol condensation as key step. The WST-1 cell proliferation assay showed that they have greater anti-proliferative potency than curcumin, quercetin, and genistein on both androgen-dependent and androgen-independent human prostate cancer cells. PMID:26341135

  7. Enhanced stability of a naringenin/2,6-dimethyl β-cyclodextrin inclusion complex: molecular dynamics and free energy calculations based on MM- and QM-PBSA/GBSA.

    Science.gov (United States)

    Sangpheak, Waratchada; Khuntawee, Wasinee; Wolschann, Peter; Pongsawasdi, Piamsook; Rungrotmongkol, Thanyada

    2014-05-01

    The structure, dynamic behavior and binding affinity of the inclusion complexes between naringenin and the two cyclodextrins (CDs), β-CD and its 2,6-dimethyl derivative (DM-β-CD), were theoretically studied by multiple molecular dynamics simulations and free energy calculations. Naringenin most likely prefers to bind with CDs through the phenyl ring. Although a lower hydrogen bond formation of naringenin with the 3-hydroxyl group of DM-β-CD (relative to β-CD) was observed, the higher cavity could encapsulate almost the whole naringenin molecule. In contrast for the naringenin/β-CD complex, the phenyl ring feasibly passed through the primary rim resulting in the chromone ring binding inside instead. MM-PBSA/GBSA and QM-PBSA/GBSA binding free energies strongly suggested a greater stability of the naringenin/DM-β-CD inclusion complex. Van der Waals force played an important role as the key guest-host interaction for the complexation between naringenin and each cyclodextrin. PMID:24681901

  8. A model for family replication and a mechanism for mass hierarchy

    International Nuclear Information System (INIS)

    We suggest a flavon-chromon preon model possessing two preonic scales - Λsub(M)>>1 TeV and Λsub(H)approx.=1 TeV - associated with metacolor and hypercolor gauge forces respectively. The model exhibits two desirable features: (a) a mechanism for family replication, and (b) a new mechanism for interfamily mass hierarchy. With a minimal choice of the preonic fields, the model predicts four families (e, μ, tau and tau') tau being a replication of e and tau' of μ. Barring mixing, the e- and μ-families are bound by the metacolor force and have a small size approx.=Λsub(M)-1, while the tau and the tau', which are composites of composites, are bound by the hypercolor force and have a relatively large size approx.=Λsub(H)-1. The model predicts that the next-generation accelerators should discover (a) compositeness of quarks and leptons, primarily through family non-diagonal processes like (e-e+ or qsub(e)anti qsub(e))->tau-tau+, qsub(b)anti qsub(b) or psub(t)anti qsub(t), and (b) a breakdown of e-μ-tau universality. It also predicts observable rare decays like tau->eγ and Ksub(L)->anti μe. (orig.)

  9. Mass spectrometry-based metabolite profiling and antioxidant activity of Aloe vera ( Aloe barbadensis Miller) in different growth stages.

    Science.gov (United States)

    Lee, Sarah; Do, Seon-Gil; Kim, Sun Yeou; Kim, Jinwan; Jin, Yoojeong; Lee, Choong Hwan

    2012-11-14

    Metabolite profiling of four different-sized Aloe vera plants was performed using gas chromatography-ion trap-mass spectrometry (GC-IT-MS) and ultra performance liquid chromatography-quadrupole-time of flight-mass spectrometry (UPLC-Q-TOF-MS) with multivariate analysis. Amino acids, sugars, and organic acids related to growth and development were identified by sizes. In particular, the relative contents of glucose, fructose, alanine, valine, and aspartic acid increased gradually as the size of the aloe increased. Anthraquinone derivatives such as 7-hydroxy-8-O-methylaloin, 7-hydroxyaloin A, and 6'-malonylnataloins A and B increased gradually, whereas chromone derivatives decreased continuously as the size of the aloe increased. The A30 aloe (size = 20-30 cm) with relatively high contents of aloins A and B, was suggested to have antioxidant components showing the highest antioxidant activity among the four different sizes of aloe. These data suggested that MS-based metabolomic approaches can illuminate metabolite changes associated with growth and development and can explain their change of antioxidant activity. PMID:23050594

  10. Fibril stability in solutions of twisted -sheet peptides: a new kind of micellization in chiral systems

    Science.gov (United States)

    Nyrkova, I. A.; Semenov, A. N.; Aggeli, A.; Boden, N.

    2000-10-01

    The problem of fibril (fibre) formation in chiral systems is explored theoretically being supported by experiments on synthetic de novo 11-mer peptide forming self-assembled -sheet tapes. Experimental data unambiguously indicate that the tapes form fibrils of nearly monodisperse thickness ca. 8-10 nm. Fibril formation and stabilisation are attributed to inter-tape face-to-face attraction and their intrinsic twist, correspondingly. The proposed theory is capable of predicting the fibril aggregation number and its equilibrium twist in terms of molecular parameters of the primary tapes. The suggested novel mechanism of twist stabilisation of finite aggregates (fibrils) is different to the well-known stabilisation of micelles in amphiphilic systems, and it is likely to explain the formation and stability of fibrils in a wide variety of systems including proteinaceous amyloid fibres, sickle-cell hemoglobin fibres responsible for HbS anemia, corkscrew threads found in chromonics in the presence of chiral additives and native cellulose microfibrillar crystallites. The theory also makes it possible to extract the basic molecular parameters of primary tapes (inter-tape attraction energy, helical twist step, elastic moduli) from the experimental data.

  11. Lipophilic Constituents of Rumex vesicarius L. and Rumex dentatus L.

    Science.gov (United States)

    Abou Elfotoh, Mona A.; Shams, Khaled A.; Anthony, Kevin P.; Shahat, Abdelaaty A.; Ibrahim, Magda T.; Abdelhady, Nevein M.; Abdel Azim, Nahla S.; Hammouda, Faiza M.; El-Missiry, Mostafa M.; Saleh, Mahmoud A.

    2013-01-01

    Rumex dentatus L. and Rumex vesicarius L., of the family Polygonaceae, are edible herbs growing wild in Egypt. Their lipoid constituents were examined by both liquid chromatography/mass spectrometry (LC/MS) and by gas chromatography/mass spectrometry (GC/MS). Their essential oil compositions consisted mainly of thujene, limonene, fenchon, estragole, and anethole but at largely different concentration. Fatty acid compositions were similar among the two species and consisting of palmitic, oleic, linoleic and linolenic acids, with R. vesicarius containing much higher level of omega-3-fatty acids. Both of the crude lipid extracts of the two species showed strong antioxidant activity as a radical quenching agent against 2,2-diphenyl-1-picrylhydrazyl (DPPH) systems. Antioxidant activities were mostly associated with the polar lipid fractions. High performance thin layer chromatography (HPTLC), both in the normal and reversed phase, as well as liquid chromatography/mass spectrometry (LC/MS) in the positive and negative electrospray ionization (ESI), showed unique chemical profile for each species that can be useful for species identification and quality control of herbal drug formulations. R. vesicarius was characterized by abundances of flavonoids and R. dentatus was abundant in anthraquinones and chromones. PMID:26784344

  12. H-bonding directed programmed supramolecular assembly of naphthalene-diimide (NDI) derivatives.

    Science.gov (United States)

    Das, Anindita; Ghosh, Suhrit

    2016-05-25

    In this review we have collated various supramolecular designs, all surrounding H-bonding among well-known functional groups (peptides, nucleic acids, amides, ureas, carboxylic acids, pyridine-hydroxyls, urethanes, imides and others), to dictate self-assembly of naphthalenediimide (NDI) π-systems (both small molecules and polymeric building blocks) that exhibit several exciting features including strong propensity for π-π interactions, π-acidity, excellent n-type semiconductivity, CT-complexation, ion-π interactions, ring-substitution dependent redox properties and photophysical properties. This article reveals that H-bonding can indeed serve as a very powerful and versatile tool to programmed self-assembly of a single or multiple dye system producing a wide range of tailored soft materials, including fibrillar gels, chromonic mesophases, foldamers, nanotubes, vesicles, reverse micelles and polymersomes, both in water and organic medium with distinct photophysical properties, charge transport properties, conductivity properties and functional group displays that are highly relevant in the fields of biology and organic electronics. PMID:27100059

  13. Inhibition of NF-kB activation and cytokines production in THP-1 monocytes by 2-styrylchromones.

    Science.gov (United States)

    Gomes, Ana; Capela, João P; Ribeiro, Daniela; Freitas, Marisa; Silva, Artur M S; Pinto, Diana C G A; Santos, Clementina M M; Cavaleiro, José A S; Lima, José L F C; Fernandes, Eduarda

    2015-01-01

    Nuclear factor kappa B (NF-kB) is one of the most important transcription factors whose modulation triggers a cascade of signaling events, namely the expression of many cytokines, enzymes, chemokines, and adhesion molecules, some of which being potential key targets for intervention in the treatment of inflammatory conditions. The 2-styrylchromones (2-SC) designation represents a well-recognized group of natural and synthetic chromones, vinylogues of flavones (2-phenylchromones). Several 2-SC were recently tested for their anti-inflammatory potential, regarding the arachidonic acid metabolic cascade, showing some motivating results. In addition, several flavones with structural similarities to 2-SC have shown NF-kB inhibitory properties. Hence, the aim of the present work was to continue the investigation on the interference of 2-SC in inflammatory pathways. Herein we report their effects on lipopolysaccharide (LPS)-induced NF-kB activation and consequent production of proinflammatory cytokines/chemokine, using a human monocytic cell line (THP-1). From the twelve 2-SC tested, three of them were able to significantly inhibit the NF-kB activation and to reduce the production of the proinflammatory cytokines/chemokine. The compound 3',4',5-trihydroxy-2- styrylchromone stood up as the most active in both assays, being a promising candidate for an anti-inflammatory drug. PMID:25665653

  14. Establishment of Aquilaria malaccensis Callus, cell suspension and adventitious root systems

    International Nuclear Information System (INIS)

    Aquilaria malaccensis is a tropical forest tree from the family Thymelaeaceae, an endangered forest species and was listed in CITES since 1995. Locally known as Pokok Karas, this tree produces agar wood or gaharu, a highly valuable, resinous and fragrant forest product. Karas has been highly recognized for its vast medicinal values and gaharu has been widely use for perfumery, incense and religious purposes. The phyto chemical studies of agar wood showed that Sesqui terpenoid and Phenyl ethy chromone derivatives are the principal compounds that have anti allergic and anti microbe activities. Cell and organ culture systems provide large scale production of biomass and offers feasibilities for the production of secondary metabolites. This paper describes the work done for establishing reproducible systems for callus initiation and production of cell suspension cultures as well as production of adventitious roots that will later be amenable for the production of secondary metabolites of A. malaccensis. Hence, further manipulation with Methyl Jasmonate, a chemical elicitor could be done to induce secondary metabolites using callus, cell suspension and adventitious roots systems. (author)

  15. Plant-Derived Antimalarial Agents: New Leads and Efficient Phytomedicines. Part II. Non-Alkaloidal Natural Products

    Directory of Open Access Journals (Sweden)

    Alaíde Braga de Oliveira

    2009-08-01

    Full Text Available Malaria is still the most destructive and dangerous parasitic infection in many tropical and subtropical countries. The burden of this disease is getting worse, mainly due to the increasing resistance of Plasmodium falciparum against the widely available antimalarial drugs. There is an urgent need for new, more affordable and accessible antimalarial agents possessing original modes of action. Natural products have played a dominant role in the discovery of leads for the development of drugs to treat human diseases, and this fact anticipates that new antimalarial leads may certainly emerge from tropical plant sources. This present review covers most of the recently-published non-alkaloidal natural compounds from plants with antiplasmodial and antimalarial properties, belonging to the classes of terpenes, limonoids, flavonoids, chromones, xanthones, anthraquinones, miscellaneous and related compounds, besides the majority of papers describing antiplasmodial crude extracts published in the last five years not reviewed before. In addition, some perspectives and remarks on the development of new drugs and phytomedicines for malaria are succinctly discussed.

  16. Individual behavior and pairwise interactions between microswimmers in anisotropic liquid

    Science.gov (United States)

    Sokolov, Andrey; Zhou, Shuang; Lavrentovich, Oleg D.; Aranson, Igor S.

    2015-01-01

    A motile bacterium swims by generating flow in its surrounding liquid. Anisotropy of the suspending liquid significantly modifies the swimming dynamics and corresponding flow signatures of an individual bacterium and impacts collective behavior. We study the interactions between swimming bacteria in an anisotropic environment exemplified by lyotropic chromonic liquid crystal. Our analysis reveals a significant localization of the bacteria-induced flow along a line coaxial with the bacterial body, which is due to strong viscosity anisotropy of the liquid crystal. Despite the fact that the average viscosity of the liquid crystal is two to three orders of magnitude higher than the viscosity of pure water, the speed of bacteria in the liquid crystal is of the same order of magnitude as in water. We show that bacteria can transport a cargo (a fluorescent particle) along a predetermined trajectory defined by the direction of molecular orientation of the liquid crystal. We demonstrate that while the hydrodynamic interaction between flagella of two close-by bacteria is negligible, the observed convergence of the swimming speeds as well as flagella waves' phase velocities may occur due to viscoelastic interaction between the bacterial bodies.

  17. Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity.

    Science.gov (United States)

    Liu, Hong-Shan; Xu, Shi-Qing; Cheng, Ming; Chen, Ying; Xia, Peng; Qian, Keduo; Xia, Yi; Yang, Zheng-Yu; Chen, Chin-Ho; Morris-Natschke, Susan L; Lee, Kuo-Hsiung

    2011-10-01

    Six 3'R,4'R-di-O-(S)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) and two 3'R,4'R-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were designed, synthesized, and evaluated for inhibition of HIV-1(NL4-3) replication in TZM-bl cells. 2-Ethyl-2'-monomethyl-1'-oxa- and -1'-thia-DCP (5a, 6a), as well as 2-ethyl-1'-thia-DCP (7a) exhibited potent anti-HIV activity with EC(50) values of 30, 38 and 54 nM and therapeutic indexes of 152.6, 48.0 and 100.0, respectively, which were better than or comparable to those of the lead compound 2-ethyl-DCP in the same assay. 4-Methyl-1'-thia-DCK (8a) also showed significant inhibitory activity with an EC(50) of 128 nM and TI of 237.9. PMID:21871800

  18. Anti-AIDS agents 79. Design, synthesis, molecular modeling and structure-activity relationships of novel dicamphanoyl-2',2'-dimethyldihydropyranochromone (DCP) analogs as potent anti-HIV agents.

    Science.gov (United States)

    Zhou, Ting; Shi, Qian; Chen, Chin-Ho; Zhu, Hao; Huang, Li; Ho, Phong; Lee, Kuo-Hsiung

    2010-09-15

    In a continued study, 23 3'R,4'R-di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) derivatives (5-27) were synthesized, and screened for anti-HIV activity against both a non-drug-resistant NL4-3 strain and multiple reverse transcriptase (RT) inhibitor-resistant (RTMDR-1) strain, using 2-EDCP (4) and 2-MDCP (35) as controls. New DCP analogs 5, 9, 14, and 22 exhibited potent anti-HIV activity against HIVNL4-3 with EC50 and therapeutic index (TI) values ranging from 0.036 microM to 0.14 microM and from 110 to 420, respectively. Compounds 5 and 9 also exhibited good activity against RTMDR-1 (EC50 0.049 and 0.054 microM; TI 310 and 200, respectively), and were twofold more potent than the leads 4 and 35 (EC50 0.11 and 0.19 microM; TI 60 and 58, respectively). Evaluation of water solubility showed that 5 and 22 were 5-10 times more water soluble than 4. Quantitative structure-activity relationship (QSAR) modeling results were first performed on this compound type, and the models should aid in design of future anti-HIV DCP analogs and potential clinical drug candidates. PMID:20728367

  19. Anti-AIDS agents 79. Design, synthesis, molecular modeling and structure-activity relationships of novel dicamphanoyl-2′,2′-dimethyldihydropyranochromone (DCP) analogs as potent anti-HIV agents

    Science.gov (United States)

    Zhou, Ting; Shi, Qian; Chen, Chin-Ho; Zhu, Hao; Huang, Li; Ho, Phong; Lee, Kuo-Hsiung

    2010-01-01

    In a continued study, 23 3′R,4′R-di-O-(−)-camphanoyl-2′,2′-dimethyldihydropyrano[2,3-f]chromone (DCP) derivatives (5–27) were synthesized, and screened for anti-HIV activity against both a non-drug-resistant NL4-3 strain and multiple reverse transcriptase (RT) inhibitor-resistant (RTMDR-1) strain, using 2-EDCP (4) and 2-MDCP (35) as controls. New DCP analogs 5, 9, 14, and 22 exhibited potent anti-HIV activity against HIVNL4-3 with EC50 and therapeutic index (TI) values ranging from 0.036 μM to 0.14 μM and from 110 to 420, respectively. Compounds 5 and 9 also exhibited good activity against RTMDR-1 (EC50 0.049 and 0.054 μM; TI 310 and 200, respectively), and were two-fold more potent than the leads 4 and 35 (EC50 0.11 and 0.19 μM; TI 60 and 58, respectively). Evaluation of water solubility showed that 5 and 22 were 5–10 times more water soluble than 4. Quantitative structure-activity relationship (QSAR) modeling results were first performed on this compound type, and the models should aid in design of future anti-HIV DCP analogs and potential clinical drug candidates. PMID:20728367

  20. Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E

    Directory of Open Access Journals (Sweden)

    Lorena M. C. Cursino

    2016-02-01

    Full Text Available Preparations of Deguelia duckeana, known in Brazil as timbó, are used by indigenous people to kill fish. Reinvestigation of its extracts resulted in the isolation and identification of 11 known flavonoids identified as 3,5,4’-trimethoxy-4-prenylstilbene (1, 4-methoxyderricidine (2, lonchocarpine (3, 4-hydroxylonchocarpine (4, 4-methoxylonchocarpine (5, 5-hydroxy-4’,7-dimethoxy-6-prenylflavanone (6, 4’-hydroxyisolonchocarpine (7, 4’-methoxyisolonchocarpine (8, 3’,4’,7-trimethoxyflavone (9, 3’,4’-methylenedioxy-7-methoxyflavone (10, and 2,2-dimethyl-chromone-5,4’-hydroxy-5’-methoxyflavone (11. Except for 1, 3, and 4 all of these flavonoids have been described for the first time in D. duckeana and the flavanone 6 for the first time in nature. Compounds 2, 3, 4, 7, 9, and 10 were studied for their potential to induce cell death in neuronal SK-N-SH cells. Only the chalcone 4 and the flavanone 7 significantly induced lactate dehydrogenase (LDH release, which was accompanied by activation of caspase-3 and impairment of energy homeostasis in the MTT assay and may explain the killing effect on fish. Interestingly, the flavone 10 reduced cell metabolism in the MTT assay without inducing cytotoxicity in the LDH assay. Furthermore, the flavonoids 2, 3, 4, 7, and 10 induced phosphorylation of the AMP-activated protein kinase (AMPK and the eukaryotic elongation factor 2 (eEF2. The initiation factor eIF4E was dephosphorylated in the presence of these compounds. The initiation factor eIF2alpha was not affected. Further studies are needed to elucidate the importance of the observed effects on protein synthesis and potential therapeutic perspectives.

  1. Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E.

    Science.gov (United States)

    Cursino, Lorena M C; Lima, Nerilson M; Murillo, Renato; Nunez, Cecilia V; Merfort, Irmgard; Humar, Matjaz

    2016-01-01

    Preparations of Deguelia duckeana, known in Brazil as timbó, are used by indigenous people to kill fish. Reinvestigation of its extracts resulted in the isolation and identification of 11 known flavonoids identified as 3,5,4'-trimethoxy-4-prenylstilbene (1), 4-methoxyderricidine (2), lonchocarpine (3), 4-hydroxylonchocarpine (4), 4-methoxylonchocarpine (5), 5-hydroxy-4',7-dimethoxy-6-prenylflavanone (6), 4'-hydroxyisolonchocarpine (7), 4'-methoxyisolonchocarpine (8), 3',4',7-trimethoxyflavone (9), 3',4'-methylenedioxy-7-methoxyflavone (10), and 2,2-dimethyl-chromone-5,4'-hydroxy-5'-methoxyflavone (11). Except for 1, 3, and 4 all of these flavonoids have been described for the first time in D. duckeana and the flavanone 6 for the first time in nature. Compounds 2, 3, 4, 7, 9, and 10 were studied for their potential to induce cell death in neuronal SK-N-SH cells. Only the chalcone 4 and the flavanone 7 significantly induced lactate dehydrogenase (LDH) release, which was accompanied by activation of caspase-3 and impairment of energy homeostasis in the MTT assay and may explain the killing effect on fish. Interestingly, the flavone 10 reduced cell metabolism in the MTT assay without inducing cytotoxicity in the LDH assay. Furthermore, the flavonoids 2, 3, 4, 7, and 10 induced phosphorylation of the AMP-activated protein kinase (AMPK) and the eukaryotic elongation factor 2 (eEF2). The initiation factor eIF4E was dephosphorylated in the presence of these compounds. The initiation factor eIF2alpha was not affected. Further studies are needed to elucidate the importance of the observed effects on protein synthesis and potential therapeutic perspectives. PMID:26861281

  2. Chemical constituents of Papulaspora immersa, an endophyte from Smallanthus sonchifolius (Asteraceae), and their cytotoxic activity.

    Science.gov (United States)

    Gallo, Margareth Borges Coutinho; Cavalcanti, Bruno Coêlho; Barros, Francisco Washington Araújo; Odorico de Moraes, Manoel; Costa-Lotufo, Letícia Veras; Pessoa, Cláudia; Bastos, Jairo Kenupp; Pupo, Mônica Tallarico

    2010-12-01

    Papulaspora immersa H. H. Hotson was isolated from roots and leaves of Smallanthus sonchifolius (Poepp. and Endl.) H. Rob. (Asteraceae), traditionally known as Yacon. The fungus was cultured in rice, and, from the AcOEt fraction, 14 compounds were isolated. Among them, (22E,24R)-8,14-epoxyergosta-4,22-diene-3,6-dione (4), 2,3-epoxy-1,2,3,4-tetrahydronaphthalene-c-1,c-4,8-triol (10), and the chromone papulasporin (13) were new secondary metabolites. The spectral data of the known natural products were compared with the literature data, and their structures were established as the (24R)-stigmast-4-en-3-one (1), 24-methylenecycloartan-3β-ol (2), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (3), (-)-(3R,4R)-4-hydroxymellein (5), (-)-(3R)-5-hydroxymellein (6), 6,8-dihydroxy-3-methylisocoumarin (7), (-)-(4S)-4,8-dihydroxy-α-tetralone (8), naphthalene-1,8-diol (9), 6,7,8-trihydroxy-3-methylisocoumarin (11), 7-hydroxy-2,5-dimethylchromone (12), and tyrosol (14). Compound 4 showed the highest cytotoxic activity against the human tumor cell lines MDA-MB435 (melanoma), HCT-8 (colon), SF295 (glioblastoma), and HL-60 (promyelocytic leukemia), with IC₅₀ values of 3.3, 14.7, 5.0 and 1.6 μM, respectively. Strong synergistic effects were also observed with compound 5 and some of the isolated steroidal compounds. PMID:21162007

  3. Hierarchical organization in liquid crystal-in-liquid crystal emulsions.

    Science.gov (United States)

    Mushenheim, Peter C; Abbott, Nicholas L

    2014-11-21

    We report the formation and characterization of hierarchical ordering in systems comprised of micrometer-sized droplets of thermotropic nematic liquid crystals (LCs) dispersed in continuous nematic phases of a lyotropic chromonic LC (disodium cromoglycate (DSCG)). Significantly, we find the orientations of the two LC phases to be coupled, with nematic droplets of 4'-pentyl-4-cyanobiphenyl (5CB) exhibiting a bipolar configuration with an axis of symmetry aligned orthogonal to the far-field director of the DSCG phase. We determine that this coupling of orientations does not result from either anisometric LC droplet shape or interfacial ionic phenomena but rather is consistent with the influence of van der Waals interactions that arise from the anisotropic polarizabilities of nematic 5CB (Δn = +0.18) and DSCG (Δn = -0.02) phases. We also find that it is possible to rotate and uniformly align the nematic droplets by using a weak magnetic field (B ∼ 0.3 T). An analysis of the dynamics of relaxation of the orientations of the 5CB droplets following removal of the magnetic field reveals the DSCG and 5CB droplets to be coupled by energies of ∼10(4) kT, consistent with a simple theoretical estimate of the influence of anisotropic van der Waals interactions. We also observed the nematic 5CB droplets to form dimers and larger assemblies mediated by the elasticity of the nematic DSCG. Overall, these results reveal that LC-in-LC emulsions define a new class of hierarchically ordered soft matter in which both thermotropic and lyotropic LCs are coupled in their ordering. PMID:25278032

  4. QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Duchowicz, Pablo R., E-mail: pabloducho@gmail.com [Instituto de Investigaciones Fisicoquimicas Teoricas y Aplicadas INIFTA (UNLP, CCT La Plata-CONICET), Diag. 113 y 64, Sucursal 4, C.C. 16, 1900 La Plata (Argentina); Goodarzi, Mohammad [Instituto de Investigaciones Fisicoquimicas Teoricas y Aplicadas INIFTA (UNLP, CCT La Plata-CONICET), Diag. 113 y 64, Sucursal 4, C.C. 16, 1900 La Plata (Argentina); Ocsachoque, Marco A. [Centro de Investigacion y Desarrollo en Ciencias Aplicadas ' Dr. J. J. Ronco' (CINDECA), Departamento de Quimica, Facultad de Ciencias Exactas, UNLP-CONICET. Calle 47 No 257, B1900AJK La Plata (Argentina); Romanelli, Gustavo P. [Centro de Investigacion y Desarrollo en Ciencias Aplicadas ' Dr. J. J. Ronco' (CINDECA), Departamento de Quimica, Facultad de Ciencias Exactas, UNLP-CONICET. Calle 47 No 257, B1900AJK La Plata (Argentina); Catedra de Quimica Organica, Facultad de Ciencias Agrarias y Forestales, UNLP. Calles 60 y 119, B1904AAN La Plata (Argentina); Ortiz, Erlinda del V. [Facultad de Tecnologia y Ciencias Aplicadas, Universidad Nacional de Catamarca, Av. Maximio Victoria 55, (4700), Catamarca (Argentina); Autino, Juan C.; Bennardi, Daniel O.; Ruiz, Diego M. [Catedra de Quimica Organica, Facultad de Ciencias Agrarias y Forestales, UNLP. Calles 60 y 119, B1904AAN La Plata (Argentina); Castro, Eduardo A. [Instituto de Investigaciones Fisicoquimicas Teoricas y Aplicadas INIFTA (UNLP, CCT La Plata-CONICET), Diag. 113 y 64, Sucursal 4, C.C. 16, 1900 La Plata (Argentina)

    2009-12-20

    We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The pED{sub 50} feeding inhibition on Spodoptera litura species exhibited by aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure-Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds. After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results. The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure-activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-({alpha}-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted pED{sub 50} = 1.162.

  5. New non-toxic transition metal nanocomplexes and Zn complex-silica xerogel nanohybrid: Synthesis, spectral studies, antibacterial, and antitumor activities

    Science.gov (United States)

    Shebl, Magdy; Saif, M.; Nabeel, Asmaa I.; Shokry, R.

    2016-08-01

    A new chromone Schiff base and its complexes of Cu(II), Ni(II), Co(II), Fe(III), Zn(II), Cd(II), and UO2(VI) as well as Zn(II) complex-silica xerogel nanohybrid were successfully prepared in a nano domain with crystalline or amorphous structures. Structures of the Schiff base and its complexes were investigated by elemental and thermal analyses, IR, 1H NMR, electronic, ESR, mass spectra, XRD, and TEM, as well as conductivity and magnetic susceptibility measurements. The spectroscopic data revealed that the Schiff base ligand behaves as a monobasic tridentate ligand. The coordination sites with metal ions are γ-pyrone oxygen, azomethine nitrogen, and oxygen of the carboxylic group. The metal complexes exhibited octahedral geometry, except Cu(II) complex, which has a square planar geometry and UO2(VI) complex, in which uranium ion is hepta-coordinated. Transmission electron microscope (TEM) analysis showed that Ni(II) and Zn(II) complexes have aggregated spheres and rod morphologies, respectively. TEM images of Zn(II) complex-silica xerogel nanohybrid showed a nanosheet morphology with 46 nm average size and confirmed that the complex was uniformly distributed into the silica pores. The obtained nanocomplexes were tested as antimicrobial and antitumor agents. The results showed that Zn(II) nanocomplex and Zn(II) complex-silica xerogel nanohybrid have high activity. The toxicity test on mice showed that Zn(II) complex and Zn(II) complex-silica xerogel nanohybrid have lower toxicity than cisplatin.

  6. Study on the complexation of isoquercitrin with β-cyclodextrin and its derivatives by spectroscopy

    International Nuclear Information System (INIS)

    The inclusion complexes of isoquercitrin (IQ) with cyclodextrins (CDs) including β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD) and dimethyl-β-cyclodextrin (DM-β-CD) have been investigated using the methods of steady-state fluorescence, UV-vis absorption and induced circular dichroism. The stoichiometric ratio of the three complexes was found to be 1:1 and the stability constants (K) were estimated from spectrofluorometric titrations, as well as the thermodynamic parameters. Maximum inclusion ability was measured in the case of DM-β-CD due to the increased hydrophobicity of the host cavity, followed by HP-β-CD and β-CD. The effect of pH on the complexation process was also quantitatively assessed. IQ exists in different molecular forms depending on pH and β-CDs were most suitable for inclusion of the neutral form of IQ. The phase-solubility diagrams obtained with β-CD, HP-β-CD and DM-β-CD were all classical AL type. And DM-β-CD provided the best solubility enhancement, 12.3-fold increase compared to 2.8- and 7.5-fold increase for β-CD and HP-β-CD. The apparent stability constants obtained from the solubility data at 25 deg. C were comparable with those obtained from the fluorescence assays. Moreover, 1H NMR was carried out, which revealed that the IQ favorably inserted into the inner cavity from the chromone part instead of the phenyl part, which was in agreement with molecular modeling studies.

  7. Foliar Essential Oil Glands of Eucalyptus Subgenus Eucalyptus (Myrtaceae Are a Rich Source of Flavonoids and Related Non-Volatile Constituents.

    Directory of Open Access Journals (Sweden)

    Jason Q D Goodger

    Full Text Available The sub-dermal secretory cavities (glands embedded within the leaves of Eucalyptus (Myrtaceae were once thought to be the exclusive repositories of monoterpene and sesquiterpene oils. Recent research has debunked this theory and shown that abundant non-volatile compounds also occur within foliar glands. In particular, glands of four species in subgenus Eucalyptus contain the biologically active flavanone pinocembrin. Pinocembrin shows great promise as a pharmaceutical and is predominantly plant-sourced, so Eucalyptus could be a potential commercial source of such compounds. To explore this we quantified and assessed the purity of pinocembrin in glands of 11 species of E. subg. Eucalyptus using Electro-Spray Ionisation Liquid Chromatography Mass Spectrometry of acetonitrile extracts and Gas Chromatography Mass Spectrometry analyses of hexane extracts of isolated glands which were free from other leaf tissues. Our results showed that the glands of subgenus Eucalyptus contain numerous flavanones that are structurally related to pinocembrin and often present in much greater abundance. The maximum concentration of pinocembrin was 2 mg g-1 dry leaf found in E. stellulata, whereas that of dimethylpinocembrin (5,7-dimethoxyflavanone was 10 mg g-1 in E. oreades and that of pinostrobin (5-hydroxy-7-methoxyflavanone was 12 mg g-1 in E. nitida. We also found that the flavanones are exclusively located within the foliar glands rather than distributed throughout leaf tissues. The flavanones differ from the non-methylated pinocembrin in the degree and positions of methylation. This finding is particularly important given the attractiveness of methylated flavonoids as pharmaceuticals and therapeutics. Another important finding was that glands of some members of the subgenus also contain flavanone O-glucosides and flavanone-β-triketone conjugates. In addition, glands contain free β-triketones, β-triketone heterodimers and chromone C-glucosides. Therefore, the

  8. Inclusion complexation of pinostrobin with various cyclodextrin derivatives.

    Science.gov (United States)

    Kicuntod, Jintawee; Khuntawee, Wasinee; Wolschann, Peter; Pongsawasdi, Piamsook; Chavasiri, Warinthorn; Kungwan, Nawee; Rungrotmongkol, Thanyada

    2016-01-01

    Pinostrobin (PNS) is one of the important flavonoids and can be abundantly found in the rhizomes of fingerroot (Boesenbergia rotrunda) and galangal (Alpinia galangal and Alpinia officinarum), the herbal basis of Southeast Asian cooking. Similar to other flavonoids, PNS exhibits anti-oxidative, anti-inflammatory and anti-cancer properties. However, this compound has an extremely low water solubility that limits its use in pharmaceutical applications. Beta-cyclodextrin (βCD) and its derivatives, 2,6-dimethyl-βCD (2,6-DMβCD) and the three hydroxypropyl-βCDs (2-HPβCD, 6-HPβCD and 2,6-DHPβCD), have unique properties that enhance the stability and solubility of such low-soluble guest molecules. In the present study, molecular dynamics simulations were applied to investigate the dynamics and stability of PNS inclusion complexes with βCD and its derivatives (2,6-DMβCD, 2,6-DHPβCD, 2-HPβCD and 6-HPβCD). PNS was able to form complexes with βCD and all four of its derivatives by either the chromone (C-PNS) or phenyl (P-PNS) ring dipping toward the cavity. According to the molecular mechanics-generalized Born surface area binding free energy values, the stability of the different PNS/βCD complexes was ranked as 2,6-DHPβCD>2,6-DMβCD>2-HPβCD>6-HPβCD>βCD. These theoretical results were in good agreement with the stability constants that had been determined by the solubility method. PMID:26709752

  9. Foliar Essential Oil Glands of Eucalyptus Subgenus Eucalyptus (Myrtaceae) Are a Rich Source of Flavonoids and Related Non-Volatile Constituents.

    Science.gov (United States)

    Goodger, Jason Q D; Seneratne, Samiddhi L; Nicolle, Dean; Woodrow, Ian E

    2016-01-01

    The sub-dermal secretory cavities (glands) embedded within the leaves of Eucalyptus (Myrtaceae) were once thought to be the exclusive repositories of monoterpene and sesquiterpene oils. Recent research has debunked this theory and shown that abundant non-volatile compounds also occur within foliar glands. In particular, glands of four species in subgenus Eucalyptus contain the biologically active flavanone pinocembrin. Pinocembrin shows great promise as a pharmaceutical and is predominantly plant-sourced, so Eucalyptus could be a potential commercial source of such compounds. To explore this we quantified and assessed the purity of pinocembrin in glands of 11 species of E. subg. Eucalyptus using Electro-Spray Ionisation Liquid Chromatography Mass Spectrometry of acetonitrile extracts and Gas Chromatography Mass Spectrometry analyses of hexane extracts of isolated glands which were free from other leaf tissues. Our results showed that the glands of subgenus Eucalyptus contain numerous flavanones that are structurally related to pinocembrin and often present in much greater abundance. The maximum concentration of pinocembrin was 2 mg g-1 dry leaf found in E. stellulata, whereas that of dimethylpinocembrin (5,7-dimethoxyflavanone) was 10 mg g-1 in E. oreades and that of pinostrobin (5-hydroxy-7-methoxyflavanone) was 12 mg g-1 in E. nitida. We also found that the flavanones are exclusively located within the foliar glands rather than distributed throughout leaf tissues. The flavanones differ from the non-methylated pinocembrin in the degree and positions of methylation. This finding is particularly important given the attractiveness of methylated flavonoids as pharmaceuticals and therapeutics. Another important finding was that glands of some members of the subgenus also contain flavanone O-glucosides and flavanone-β-triketone conjugates. In addition, glands contain free β-triketones, β-triketone heterodimers and chromone C-glucosides. Therefore, the foliar glands

  10. QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives

    International Nuclear Information System (INIS)

    We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The pED50 feeding inhibition on Spodoptera litura species exhibited by aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure-Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds. After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results. The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure-activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-(α-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted pED50 = 1.162.

  11. Statistical mechanics of aggregation in anisotropic solvents: kinetic energy of aggregates and universal power-law behavior far from criticality

    International Nuclear Information System (INIS)

    We propose and study analytically a statistical mechanical model of reversible aggregation in anisotropic and isotropic solvents for small solute concentrations c. An aggregate comprising n solute molecules is a one-dimensional structureless flexible rod, n-mer, which interacts with the solvent anisotropy. The solvent is a nematic liquid crystal described by its scalar order parameter. The kinetic energy of n-mers is shown to play a unique role in the thermodynamic equilibrium. The kinetic energy contribution to the partition function is modeled by the term nq, where q is determined by the persistence lengths of different translation–rotation modes (e.g. q = 5 for a rigid rod and q≈0 for a very flexible chain). The n-mer concentration is found to depend on c via its powers which are fully determined by the parameter q. The solvent anisotropy results in a larger fraction of longer aggregates and gives rise to two different aggregation regimes: a low n regime for lower solute concentration c and a high n regime for higher c. The total aggregate concentration is found to be a sum of universal power laws of c with the exponents that are different for anisotropic and isotropic solvents, but in both cases are determined solely by the parameter q. The analytical formulae for the two regimes and the crossover point (which can be naturally associated with the critical micelle concentration) are in a quantitative agreement with the numerical solution of the model. The model is pertinent to self-assemblies of plank-like dye molecules dissolved in an isotropic solvent (related to chromonic liquid crystals) and in a nematic liquid crystal

  12. Intranasal steroids: managing allergic rhinitis and tailoring treatment to patient preference.

    Science.gov (United States)

    Meltzer, Eli O

    2005-01-01

    Allergic rhinitis (AR) can have a significant impact on patient quality of life (QoL), affecting learning ability and work productivity. Both the consequences of the impairment and the costs of treatment are associated with a large economic burden. The management of AR includes allergen avoidance, pharmacotherapy, and immunotherapy. Current pharmacotherapy options are oral and intranasal antihistamines, intranasal corticosteroids (INS), intranasal chromones, oral and intranasal decongestants, oral and intranasal anticholinergic agents, and antileukotrienes. A number of guidelines recommend INS as first-line treatment for persistent and moderate-to-severe AR. Although both patient and physician concern over the long-term safety of oral systemic steroids has previously prevented widespread use of INS, it is important to note that they have a superior risk/benefit ratio compared with other monotherapies. Indeed, the limited systemic bioavailability of INS agents, when used at recommended doses, has resulted in very low rates of systemic adverse effects, as shown by a lack of either hypothalamic-pituitary-adrenal axis or growth suppression. Large, controlled clinical studies have shown comparable efficacy and safety among the newer INS; therefore, clinicians may need to consider other factors, such as good patient compliance, when selecting an appropriate INS agent for a patient. In addition, patients often prefer one agent over another, and compliance may be improved by selecting the preferred agent. The development of two new questionnaires, the Clinical Practice Patient Preference Questionnaire and the Clinical Trial Patient Preference Questionnaire, may prove useful in selecting the optimal treatment regimen for patients. PMID:16541967

  13. A chromatography-free isolation of rohitukine from leaves of Dysoxylum binectariferum: Evaluation for in vitro cytotoxicity, Cdk inhibition and physicochemical properties.

    Science.gov (United States)

    Kumar, Vikas; Guru, Santosh K; Jain, Shreyans K; Joshi, Prashant; Gandhi, Sumit G; Bharate, Sandip B; Bhushan, Shashi; Bharate, Sonali S; Vishwakarma, Ram A

    2016-08-01

    Rohitukine is a chromone alkaloid isolated from an Indian medicinal plant Dysoxylum binectariferum. This natural product has led to the discovery of two clinical candidates (flavopiridol and P276-00) for the treatment of cancer. Herein, for the first time we report an efficient protocol for isolation and purification of this precious natural product in a bulk-quantity from leaves (a renewable source) of D. binectariferum (>98% purity) without use of chromatography or any acid-base treatment. Despite of the fact that this scaffold has reached up to clinical stage, particularly for leukemia; however the antileukemic activity of a parent natural product has never been investigated. Furthermore, rohitukine has never been studied for cyclin-dependent kinase (Cdk) inhibition, kinase profiling and for its experimental physicochemical properties. Thus, herein, we report in vitro cytotoxicity of rohitukine in a panel of 20 cancer cell lines (including leukemia, pancreatic, prostate, breast and CNS) and 2 normal cell lines; kinase profiling, Cdk2/9 inhibition, and physicochemical properties (solubility and stability in biological medias, pKa, LogP, LogD). In cytotoxicity screening, rohitukine displayed promising activity in HL-60 and Molt-4 (leukemia) cell lines with GI50 of 10 and 12μM, respectively. It showed inhibition of Cdk2/A and Cdk9/T1 with IC50 values of 7.3 and 0.3μM, respectively. The key interactions of rohitukine with Cdk9 was also studied by molecular modeling. Rohitukine was found to be highly water soluble (Swater=10.3mg/mL) and its LogP value was -0.55. The ionization constant of rohitukine was found to be 5.83. Rohitukine was stable in various biological media's including rat plasma. The data presented herein will help in designing better anticancer agents in future. PMID:27363938

  14. Susceptibility of Tetranychus urticae Koch to an ethanol extract of Cnidoscolus aconitifolius leaves under laboratory conditions.

    Science.gov (United States)

    Numa, S; Rodríguez, L; Rodríguez, D; Coy-Barrera, E

    2015-01-01

    One of the main pests of commercial rose crops in Colombia is the phytophagous mite Tetranychus urticae Koch. To manage this pest, synthetic chemicals have traditionally been used, some of which are well known to be potentially toxic to the environment and humans. Therefore, alternative strategies for pest management in greenhouse crops have been developed in recent years, including biological control with natural enemies such as parasitoids, predators and entomopathogenic microorganisms as well as chemical control using plant extracts. Such extracts have shown toxicity to insects, which has positioned them as a common alternative in programs of integrated pest management. The objective of this study was to evaluate the effect of an unfractionated ethanolic extract of Cnidoscolus aconitifolius leaves on adult females of T. urticae under laboratory conditions. The extract was chemically characterized by recording its metabolic profile via liquid chromatography coupled to mass spectrometry, along with tentative metabolite identification. The immersion technique and direct application to rose leaves were used to evaluate the effects of seven doses (10-2,000 µg/mL) of the ethanol extract of C. aconitifolius leaves on T. urticae females under laboratory conditions. The mortality and oviposition of individuals were recorded at 24, 48 and 72 h. It was found that the C. aconitifolius leaf extract reduced fertility and increased mortality in a dose-dependent manner. The main metabolites identified included flavonoid- and sesquiterpene-type compounds, in addition to chromone- and xanthone-type compounds as minor constituents with potential acaricidal effects. PMID:26185740

  15. ANTIMICROBIAL AND PHYTOCHEMICAL ANALYSIS OF ALOE VERA L

    Directory of Open Access Journals (Sweden)

    Mariappan V

    2012-10-01

    radicals generated by H2O2. The results indicator that plant leaf extract had maximum DNA protective activity than gel extract against free radicals. The present study A.vera gel and leaf extract was analysed by HPLC chromatogram and should the presence of glucomannose, galactoglucoaralimannone and gluconic acid, vitamin C and also anthraquinone, phenols, and chromones.

  16. The Genus Aloe: Phytochemistry and Therapeutic Uses Including Treatments for Gastrointestinal Conditions and Chronic Inflammation.

    Science.gov (United States)

    Cock, I E

    2015-01-01

    Plants of the genus Aloe have perhaps the longest recorded history of medicinal usage and are amongst the most widely used plants for traditional medicinal purposes worldwide. Aloe vera, Aloe ferox, Aloe arborescens and Aloe perryi are the best known and most widely used, but many other species are also used for their therapeutic properties. The Aloes have been used since ancient times, particularly for the treatment of microbial infections, gastrointestinal disorders and inflammatory conditions. In addition to their myriad uses in traditional therapeutics, the Aloes have also been used as components of cosmetic formulations, and in the food and beverage industries. Despite their wide acceptance, studies from different laboratories often report wide variations in the therapeutic bioactivities from within the same Aloe species, even when the same extraction procedures are used. Furthermore, leaves from individual Aloe plants within the same species may have widely varying levels of the bioactive phytochemicals. Phytochemical analyses have shown that many Aloe species contain various carbohydrate polymers (notably glucomannans) and a range of other low molecular weight phenolic compounds including alkaloids, anthraquinones, anthrones, benzene and furan derivatives, chromones, coumarins, flavonoids, phytosterols, pyrans and pyrones. There has been a wealth of information published about the phytochemistry and therapeutic potential of the Aloes (especially Aloe vera). Much of this has been contradictory. Intra- and interspecies differences in the redox state of the individual Aloe components and in the ratios of these components may occur between individual plants. These factors may all affect the physiological properties of Aloe extracts. Due to the structure and chemical nature of many of the Aloe phytochemicals, it is likely that many of the reported medicinal properties are due to antioxidant or prooxidant effects. The antioxidant/prooxidant activities of many Aloe

  17. Condensed matter analogues of cosmology

    Science.gov (United States)

    Kibble, Tom; Srivastava, Ajit

    2013-10-01

    Ranjkesh, V Simonka, M Ambrozic, Z Bradac and S Kralj Morphogenesis of defects and tactoids during isotropic-nematic phase transition in self-assembled lyotropic chromonic liquid crystalsYoung-Ki Kim, Sergij V Shiyanovskii and Oleg D Lavrentovich Annihilation dynamics of stringlike topological defects in a nematic lyotropic liquid crystalR R Guimarães, R S Mendes, P R G Fernandes and H Mukai Duality between the dynamics of line-like brushes of point defects in 2D and strings in 3D in liquid crystalsSanatan Digal, Rajarshi Ray, P S Saumia and Ajit M Srivastava The multiuniverse transition in superfluid 3HeYury Bunkov Coherent topological defect dynamics and collective modes in superconductors and electronic crystalsD Mihailovic, T Mertelj, V V Kabanov and S Brazovskii Gaussianity revisited: exploring the Kibble-Zurek mechanism with superconducting ringsD J Weir, R Monaco, V P Koshelets, J Mygind and R J Rivers The Kibble-Zurek mechanism in a subcritical bifurcationM A Miranda, D Laroze and W González-Viñas Topological relics of symmetry breaking: winding numbers and scaling tilts from random vortex-antivortex pairsW H Zurek Causality and non-equilibrium second-order phase transitions in inhomogeneous systemsA del Campo, T W B Kibble and W H Zurek The role of causality in tunable Fermi gas condensatesJen-Tsung Hsiang, Chi-Yong Lin, Da-Shin Lee and Ray J Rivers Kibble-Zurek mechanism in a trapped ferromagnetic Bose-Einstein condensateHiroki Saito, Yuki Kawaguchi and Masahito Ueda D-brane solitons and boojums in field theory and Bose-Einstein condensatesKenichi Kasamatsu, Hiromitsu Takeuchi and Muneto Nitta Kibble-Zurek scaling and string-net coarsening in topologically ordered systemsAnushya Chandran, F J Burnell, Vedika Khemani and S L Sondhi Universal frozen spectra after time-dependent symmetry restoring phase transitionsFriedemann Queisser, Patrick Navez and Ralf Schützhold Microscopic theory of non-adiabatic response in real and imaginary timeC De Grandi, A