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Sample records for alkaloid-inspired analogues skeletal

  1. Biogenetically inspired synthesis and skeletal diversification of indole alkaloids.

    Science.gov (United States)

    Mizoguchi, Haruki; Oikawa, Hideaki; Oguri, Hiroki

    2014-01-01

    To access architecturally complex natural products, chemists usually devise a customized synthetic strategy for constructing a single target skeleton. In contrast, biosynthetic assembly lines often employ divergent intramolecular cyclizations of a polyunsaturated common intermediate to produce diverse arrays of scaffolds. With the aim of integrating such biogenetic strategies, we show the development of an artificial divergent assembly line generating unprecedented numbers of scaffold variations of terpenoid indole alkaloids. This approach not only allows practical access to multipotent intermediates, but also enables systematic diversification of skeletal, stereochemical and functional group properties without structural simplification of naturally occurring alkaloids. Three distinct modes of [4+2] cyclizations and two types of redox-mediated annulations provided divergent access to five skeletally distinct scaffolds involving iboga-, aspidosperma-, andranginine- and ngouniensine-type skeletons and a non-natural variant within six to nine steps from tryptamine. The efficiency of our approach was demonstrated by successful total syntheses of (±)-vincadifformine, (±)-andranginine and (-)-catharanthine.

  2. Design, synthesis and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists

    DEFF Research Database (Denmark)

    Crestey, François; Jensen, Anders A.; Borch, Morten

    2013-01-01

    The synthesis of a new series of Erythrina alkaloid analogues and their pharmacological characterization at various nicotine acetylcholine receptor (nAChR) subtypes are described. The compounds were designed to be simplified analogues of aromatic erythrinanes with the aim of obtaining subtype...

  3. Pyrrolizidine alkaloids.

    Science.gov (United States)

    Robertson, Jeremy; Stevens, Kiri

    2014-12-01

    This review covers pyrrolizidine alkaloids isolated from natural sources. Topics include: aspects of structure, isolation, and biological/pharmacological studies; total syntheses of necic acids, necine bases and closely-related non-natural analogues.

  4. New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids ?

    OpenAIRE

    Plodek, Alois; Bracher, Franz

    2016-01-01

    Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids...

  5. Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

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    Louis P. Sandjo

    2015-09-01

    Full Text Available This review focuses on pyridoacridine-related metabolites as one biologically interesting group of alkaloids identified from marine sources. They are produced by marine sponges, ascidians and tunicates, and they are structurally comprised of four to eight fused rings including heterocycles. Acridine, acridone, dihydroacridine, and quinolone cores are features regularly found in these alkaloid skeletons. The lack of hydrogen atoms next to quaternary carbon atoms for two or three rings makes the chemical shift assignment a difficult task. In this regard, one of the aims of this review is the compilation of previously reported, pyridoacridine 13C NMR data. Observations have been made on the delocalization of electrons and the presence of some functional groups that lead to changes in the chemical shift of some carbon resonances. The lack of mass spectra information for these alkaloids due to the compactness of their structures is further discussed. Moreover, the biosynthetic pathways of some of these metabolites have been shown since they could inspire biomimetic synthesis. The synthesis routes used to prepare members of these marine alkaloids (as well as their analogues, which are synthesized for biological purposes are also discussed. Pyridoacridines were found to have a large spectrum of bioactivity and this review highlights and compares the pharmacophores that are responsible for the observed bioactivity.

  6. Structure–function relationship of skeletal muscle provides inspiration for design of new artificial muscle

    International Nuclear Information System (INIS)

    Gao, Yingxin; Zhang, Chi

    2015-01-01

    A variety of actuator technologies have been developed to mimic biological skeletal muscle that generates force in a controlled manner. Force generation process of skeletal muscle involves complicated biophysical and biochemical mechanisms; therefore, it is impossible to replace biological muscle. In biological skeletal muscle tissue, the force generation of a muscle depends not only on the force generation capacity of the muscle fiber, but also on many other important factors, including muscle fiber type, motor unit recruitment, architecture, structure and morphology of skeletal muscle, all of which have significant impact on the force generation of the whole muscle or force transmission from muscle fibers to the tendon. Such factors have often been overlooked, but can be incorporated in artificial muscle design, especially with the discovery of new smart materials and the development of innovative fabrication and manufacturing technologies. A better understanding of the physiology and structure–function relationship of skeletal muscle will therefore benefit the artificial muscle design. In this paper, factors that affect muscle force generation are reviewed. Mathematical models used to model the structure–function relationship of skeletal muscle are reviewed and discussed. We hope the review will provide inspiration for the design of a new generation of artificial muscle by incorporating the structure–function relationship of skeletal muscle into the design of artificial muscle. (topical review)

  7. Structure-function relationship of skeletal muscle provides inspiration for design of new artificial muscle

    Science.gov (United States)

    Gao, Yingxin; Zhang, Chi

    2015-03-01

    A variety of actuator technologies have been developed to mimic biological skeletal muscle that generates force in a controlled manner. Force generation process of skeletal muscle involves complicated biophysical and biochemical mechanisms; therefore, it is impossible to replace biological muscle. In biological skeletal muscle tissue, the force generation of a muscle depends not only on the force generation capacity of the muscle fiber, but also on many other important factors, including muscle fiber type, motor unit recruitment, architecture, structure and morphology of skeletal muscle, all of which have significant impact on the force generation of the whole muscle or force transmission from muscle fibers to the tendon. Such factors have often been overlooked, but can be incorporated in artificial muscle design, especially with the discovery of new smart materials and the development of innovative fabrication and manufacturing technologies. A better understanding of the physiology and structure-function relationship of skeletal muscle will therefore benefit the artificial muscle design. In this paper, factors that affect muscle force generation are reviewed. Mathematical models used to model the structure-function relationship of skeletal muscle are reviewed and discussed. We hope the review will provide inspiration for the design of a new generation of artificial muscle by incorporating the structure-function relationship of skeletal muscle into the design of artificial muscle.

  8. Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.

    Science.gov (United States)

    Van Baelen, Gitte; Hostyn, Steven; Dhooghe, Liene; Tapolcsányi, Pál; Mátyus, Péter; Lemière, Guy; Dommisse, Roger; Kaiser, Marcel; Brun, Reto; Cos, Paul; Maes, Louis; Hajós, György; Riedl, Zsuzsanna; Nagy, Ildikó; Maes, Bert U W; Pieters, Luc

    2009-10-15

    Based on the indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3) and isoneocryptolepine (4), used as lead compounds for new antimalarial agents, a series of tricyclic and bicyclic analogues, including carbolines, azaindoles, pyrroloquinolines and pyrroloisoquinolines was synthesized and biologically evaluated. None of the bicyclic compounds was significantly active against the chloroquine-resistant strain Plasmodium falciparum K1, in contrast to the tricyclic derivatives. The tricyclic compound 2-methyl-2H-pyrido[3,4-b]indole (9), or 2-methyl-beta-carboline, showed the best in vitro activity, with an IC(50) value of 0.45 microM against P. falciparum K1, without apparent cytotoxicity against L6 cells (SI>1000). However, this compound was not active in the Plasmodium berghei mouse model. Structure-activity relationships are discussed and compared with related naturally occurring compounds.

  9. New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

    Directory of Open Access Journals (Sweden)

    Alois Plodek

    2016-01-01

    Full Text Available Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids. This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades.

  10. A novel conversion of C(19)-diterpenoid alkaloids into aconane-type diterpenes with eight-membered ring system via skeletal rearrangement of corresponding diazonium derivatives.

    Science.gov (United States)

    Ji, Hong; Chen, Qiao-Hong; Wang, Feng-Peng

    2009-03-01

    A new and efficient approach toward the conversion of C(19)-diterpenoid alkaloids into diterpenes with [6+8+5+6] ring system is reported. Treatment of imines 5, 14, and 24 derived from the C(19)-diterpenoid alkaloids with NaNO(2)-NaOAc-HOAc afforded a series of novel rearrangement diterpenes 6-8, 15-19, and 25-27, respectively. The lactone 11 was obtained in 41% yield by treating 5 with NaNO(2)-HBr-Br(2). The formation of diazonium intermediate is postulated, which was subsequently subjected to skeletal rearrangement, leading to the enlargement of B ring. All the new compounds were isolated and fully characterized.

  11. Indole Alkaloids Inhibiting Neural Stem Cell from Uncaria rhynchophylla

    OpenAIRE

    Wei, Xin; Jiang, Li-Ping; Guo, Ying; Khan, Afsar; Liu, Ya-Ping; Yu, Hao-Fei; Wang, Bei; Ding, Cai-Feng; Zhu, Pei-Feng; Chen, Ying-Ying; Zhao, Yun-Li; Chen, Yong-Bing; Wang, Yi-Fen; Luo, Xiao-Dong

    2017-01-01

    Uncaria rhynchophylla is commonly recognized as a traditional treatment for dizziness, cerebrovascular diseases, and nervous disorders in China. Previously, the neuro-protective activities of the alkaloids from U. rhynchophylla were intensively reported. In current work, three new indole alkaloids (1–3), identified as geissoschizic acid (1), geissoschizic acid N 4-oxide (2), and 3β-sitsirikine N 4-oxide (3), as well as 26 known analogues were isolated from U. rhynchophylla. However, in the ne...

  12. Energy capture and storage in asymmetrically multistable modular structures inspired by skeletal muscle

    Science.gov (United States)

    Kidambi, Narayanan; Harne, Ryan L.; Wang, K. W.

    2017-08-01

    The remarkable versatility and adaptability of skeletal muscle that arises from the assembly of its nanoscale cross-bridges into micro-scale assemblies known as sarcomeres provides great inspiration for the development of advanced adaptive structures and material systems. Motivated by the capability of cross-bridges to capture elastic strain energy to improve the energetic efficiency of sudden movements and repeated motions, and by models of cross-bridge power stroke motions and sarcomere contractile behaviors that incorporate asymmetric, bistable potential energy landscapes, this research develops and studies modular mechanical structures that trap and store energy in higher-energy configurations. Modules exhibiting tailorable asymmetric bistability are first designed and fabricated, revealing how geometric parameters influence the asymmetry of the resulting double-well energy landscapes. These experimentally-observed characteristics are then investigated with numerical and analytical methods to characterize the dynamics of asymmetrically bistable modules. The assembly of such modules into greater structures generates complex, multi-well energy landscapes with stable system configurations exhibiting different quantities of stored elastic potential energy. Dynamic analyses illustrate the ability of these structures to capture a portion of the initial kinetic energy due to impulsive excitations as recoverable strain potential energy, and reveal how stiffness parameters, damping, and the presence of thermal noise in micro- and nano-scale applications influence energy capture behaviors. The insights gained could foster the development of advanced structural/material systems inspired by skeletal muscle, including actuators that effectively capture, store, and release energy, as well as adaptive, robust, and reusable armors and protective devices.

  13. Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis.

    Science.gov (United States)

    Robertson, Jeremy; Stevens, Kiri

    2017-01-04

    Covering: 2013 up to the end of 2015This review covers the isolation and structure of new pyrrolizidines; pyrrolizidine biosynthesis; biological activity, including the occurrence of pyrrolizidines as toxic components or contaminants in foods and beverages; and formal and total syntheses of naturally-occurring pyrrolizidine alkaloids and closely related non-natural analogues.

  14. Design, synthesis, antiviral activity and mode of action of phenanthrene-containing N-heterocyclic compounds inspired by the phenanthroindolizidine alkaloid antofine.

    Science.gov (United States)

    Yu, Xiuling; Wei, Peng; Wang, Ziwen; Liu, Yuxiu; Wang, Lizhong; Wang, Qingmin

    2016-02-01

    The phenanthroindolizidine alkaloid antofine and its analogues have excellent antiviral activity against tobacco mosaic virus (TMV). To simplify the structure and the synthesis of the phenanthroindolizidine alkaloid, a series of phenanthrene-containing N-heterocyclic compounds (compounds 1 to 33) were designed and synthesised, based on the intermolecular interaction of antofine and TMV RNA, and systematically evaluated for their anti-TMV activity. Most of these compounds exhibited good to reasonable anti-TMV activity. The optimum compounds 5, 12 and 21 displayed higher activity than the lead compound antofine and commercial ribavirin. Compound 12 was chosen for field trials of antiviral efficacy against TMV, and was found to exhibit better activity than control plant virus inhibitors. Compounds 5 and 12 were chosen for mode of action studies. The changes in fluorescence intensity of compounds 5 and 12 on separated TMV RNA showed that these small molecules can also bind to TMV RNA, but the mode is very different from that of antofine. The compounds combining phenanthrene and an N-heterocyclic ring could maintain the anti-TMV activity of phenanthroindolizidines, but their modes of action are different from that of antofine. The present study lays a good foundation for us to find more efficient anti-plant virus reagents. © 2015 Society of Chemical Industry.

  15. Hexacyclic monoterpenoid indole alkaloids from Rauvolfia verticillata.

    Science.gov (United States)

    Gao, Yuan; Yu, Ai-Lin; Li, Gen-Tao; Hai, Ping; Li, Yan; Liu, Ji-Kai; Wang, Fei

    2015-12-01

    Five new hexacyclic monoterpenoid indole alkaloids, rauvovertine A (1), 17-epi-rauvovertine A (2), rauvovertine B (3), 17-epi-rauvovertine B (4), and rauvovertine C (5) together with 17 known analogues were isolated from the stems of Rauvolfia verticillata. Compounds 1/2 and 3/4 were obtained as C-17 epimeric mixtures due to rapid hemiacetal tautomerism in solution. The structures of 1-5 were established by spectroscopic analysis and with the aid of molecular modeling. The new alkaloids were evaluated for their cytotoxicity in vitro against human tumor HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. Copyright © 2015 Elsevier B.V. All rights reserved.

  16. Effects of Trigonelline, an Alkaloid Present in Coffee, on Diabetes-Induced Disorders in the Rat Skeletal System.

    Science.gov (United States)

    Folwarczna, Joanna; Janas, Aleksandra; Pytlik, Maria; Cegieła, Urszula; Śliwiński, Leszek; Krivošíková, Zora; Štefíková, Kornélia; Gajdoš, Martin

    2016-03-02

    Diabetes increases bone fracture risk. Trigonelline, an alkaloid with potential antidiabetic activity, is present in considerable amounts in coffee. The aim of the study was to investigate the effects of trigonelline on experimental diabetes-induced disorders in the rat skeletal system. Effects of trigonelline (50 mg/kg p.o. daily for four weeks) were investigated in three-month-old female Wistar rats, which, two weeks before the start of trigonelline administration, received streptozotocin (60 mg/kg i.p.) or streptozotocin after nicotinamide (230 mg/kg i.p.). Serum bone turnover markers, bone mineralization, and mechanical properties were studied. Streptozotocin induced diabetes, with significant worsening of bone mineralization and bone mechanical properties. Streptozotocin after nicotinamide induced slight glycemia increases in first days of experiment only, however worsening of cancellous bone mechanical properties and decreased vertebral bone mineral density (BMD) were demonstrated. Trigonelline decreased bone mineralization and tended to worsen bone mechanical properties in streptozotocin-induced diabetic rats. In nicotinamide/streptozotocin-treated rats, trigonelline significantly increased BMD and tended to improve cancellous bone strength. Trigonelline differentially affected the skeletal system of rats with streptozotocin-induced metabolic disorders, intensifying the osteoporotic changes in streptozotocin-treated rats and favorably affecting bones in the non-hyperglycemic (nicotinamide/streptozotocin-treated) rats. The results indicate that, in certain conditions, trigonelline may damage bone.

  17. Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.

    Science.gov (United States)

    Wang, Yue-Hu; Goto, Masuo; Wang, Li-Ting; Hsieh, Kan-Yen; Morris-Natschke, Susan L; Tang, Gui-Hua; Long, Chun-Lin; Lee, Kuo-Hsiung

    2014-10-15

    Twenty-five amide alkaloids (1-25) from Piper boehmeriifolium and 10 synthetic amide alkaloid derivatives (39-48) were evaluated for antiproliferative activity against eight human tumor cell lines, including chemosensitive and multidrug-resistant (MDR) cell lines. The results suggested tumor type-selectivity. 1-[7-(3,4,5-Trimethoxyphenyl)heptanoyl]piperidine (46) exhibited the best inhibitory activity (IC50=4.94 μM) against the P-glycoprotein (P-gp)-overexpressing KBvin MDR sub-line, while it and all other tested compounds, except 9, were inactive (IC50 >40 μM) against MDA-MB-231 and SK-BR-3. Structure-activity relationships (SARs) indicated that (i) 3,4,5-trimethoxy phenyl substitution is critical for selectivity against KBvin, (ii) the 4-methoxy group in this pattern is crucial for antiproliferative activity, (iii) double bonds in the side chain are not needed for activity, and (iv), in arylalkenylacyl amide alkaloids, replacement of an isobutylamino group with pyrrolidin-1-yl or piperidin-1-yl significantly improved activity. Further study on Piper amides is warranted, particularly whether side chain length affects the ability to overcome the MDR cancer phenotype. Copyright © 2014 Elsevier Ltd. All rights reserved.

  18. Conformational, IR spectroscopic and electronic properties of conium alkaloids and their adducts with C60 fullerene

    Science.gov (United States)

    Zabolotnyi, M. A.; Prylutskyy, Yu I.; Poluyan, N. A.; Evstigneev, M. P.; Dovbeshko, G. I.

    2016-08-01

    Conformational, IR spectroscopic and electronic properties of the components of Conium alkaloids (Conium maculatum) in aqueous environment were determined by model calculations and experiment. With the help of FT-IR spectroscopy the possibility of formation of an adduct between γ-coniceine alkaloid and C60 fullerene was demonstrated, which is important for further application of conium analogues in biomedical purposes.

  19. Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS-(--8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B and [(1S,4R,9aS-(--4-pentyloctahydro-2H-quinolizin-1-yl]methanol

    Directory of Open Access Journals (Sweden)

    de Koning Charles B

    2008-01-01

    Full Text Available Abstract Background Prior work from these laboratories has centred on the development of enaminones as versatile intermediates for the synthesis of alkaloids and other nitrogen-containing heterocycles. In this paper we describe the enantioselective synthesis of indolizidine and quinolizidine analogues of bicyclic amphibian alkaloids via pyrrolidinylidene- and piperidinylidene-containing enaminones. Results Our previously reported synthesis of racemic 8-epi-indolizidine 209B has been extended to the laevorotatory enantiomer, (--9. Attempts to adapt the synthetic route in order to obtain quinolizidine analogues revealed that a key piperidinylidene-containing enaminone intermediate (+-28 was less tractable than its pyrrolidinylidene counterpart, thereby necessitating modifications that included timing changes and additional protection-deprotection steps. A successful synthesis of [(1S,4R,9aS-4-pentyloctahydro-2H-quinolizin-1-yl]methanol (--41 from the chiral amine tert-butyl (3R-3-{benzyl [(1R-1-phenylethyl]amino}octanoate (+-14 was achieved in 14 steps and an overall yield of 20.4%. Conclusion The methodology reported in this article was successfully applied to the enantioselective synthesis of the title compounds. It paves the way for the total synthesis of a range of cis-5,8-disubstituted indolizidines and cis-1,4-disubstituted quinolizidines, as well as the naturally occurring trans-disubstituted alkaloids.

  20. Rauvotetraphyllines A-E, new indole alkaloids from Rauvolfia tetraphylla

    OpenAIRE

    Gao, Yuan; Zhou, Dong-Sheng; Kong, Ling-Mei; Hai, Ping; Li, Yan; Wang, Fei; Liu, Ji-Kai

    2012-01-01

    Five new indole alkaloids rauvotetraphyllines A–E (1–5), together with eight known analogues, were isolated from the aerial parts of Rauvolfia tetraphylla. The structures were established by means of spectroscopic methods. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0012-5 and is accessible for authorized users.

  1. Marine Natural Product Bis-indole Alkaloid Caulerpin: Chemistry and Biology.

    Science.gov (United States)

    Lunagariya, Jignesh; Bhadja, Poonam; Zhong, Shenghui; Vekariya, Rohit; Xu, Shihai

    2017-09-27

    Marine bis-indole alkaloids comprise a large and increasingly growing class of secondary metabolites, and continue to deliver a great variety of structural templates. The alkaloids derived from marine resources play a crucial role in medicinal chemistry and as chemical agents. In particular, bis-indole alkaloid caulerpin isolated from marine green algae Caulerpa and a red algae Chondria armata at various places around the world, and tested against several therapeutic areas such as anti-diabetic, antinociceptive, anti-inflammatory, anti-tumor, anti-larvicidal, anti-herpes, anti-tubercular, anti-microbial and immunostimulating activity as well as means of other chemical agents. Herein, we summarized discovery of caulerpin, and its potential medicinal and chemical applications in chronological order with various aspects. Additionally, synthesis of caulerpin, its functional analogues, and structural isomer have also been reviewed. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  2. Marine-Derived 2-Aminoimidazolone Alkaloids. Leucettamine B-Related Polyandrocarpamines Inhibit Mammalian and Protozoan DYRK & CLK Kinases

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    Nadège Loaëc

    2017-10-01

    Full Text Available A large diversity of 2-aminoimidazolone alkaloids is produced by various marine invertebrates, especially by the marine Calcareous sponges Leucetta and Clathrina. The phylogeny of these sponges and the wide scope of 2-aminoimidazolone alkaloids they produce are reviewed in this article. The origin (invertebrate cells, associated microorganisms, or filtered plankton, physiological functions, and natural molecular targets of these alkaloids are largely unknown. Following the identification of leucettamine B as an inhibitor of selected protein kinases, we synthesized a family of analogues, collectively named leucettines, as potent inhibitors of DYRKs (dual-specificity, tyrosine phosphorylation regulated kinases and CLKs (cdc2-like kinases and potential pharmacological leads for the treatment of several diseases, including Alzheimer’s disease and Down syndrome. We assembled a small library of marine sponge- and ascidian-derived 2-aminoimidazolone alkaloids, along with several synthetic analogues, and tested them on a panel of mammalian and protozoan kinases. Polyandrocarpamines A and B were found to be potent and selective inhibitors of DYRKs and CLKs. They inhibited cyclin D1 phosphorylation on a DYRK1A phosphosite in cultured cells. 2-Aminoimidazolones thus represent a promising chemical scaffold for the design of potential therapeutic drug candidates acting as specific inhibitors of disease-relevant kinases, and possibly other disease-relevant targets.

  3. Synthesis and Antimicrobial Characterization of Half-Calycanthaceous Alkaloid Derivatives

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    Shaojun Zheng

    2016-09-01

    Full Text Available A total of 29 novel tetrahydropyrroloindol-based calycanthaceous alkaloid derivatives were synthesized from indole-3-acetonitrile in good yields. The synthesized compounds were evaluated against nine strains of bacteria and a wide range of plant pathogen fungi. Bioassay results revealed that majority of the compounds displayed similar or higher in vitro antimicrobial activities than the positive control. The biological activities also indicated that substituents at R4 and R5 significantly affect the activities. Notably, compound c4 was found to be most active among the tested calycanthaceous analogues and might be a novel potential leading compound for further development as an antifungal agent. The results could pave the way for further design and structural modification of calycanthaceous alkaloids as antimicrobial agents.

  4. Alkaloids as important scaffolds in therapeutic drugs for the treatments of cancer, tuberculosis, and smoking cessation.

    Science.gov (United States)

    Kittakoop, Prasat; Mahidol, Chulabhorn; Ruchirawat, Somsak

    2014-01-01

    Alkaloid molecules can act, depending on a type of amine functionality present in alkalods, as either hydrogenacceptor or hydrogen-donor for hydrogen bonding that is critically important for the interaction (binding) between targets (enzymes, proteins and receptors) and drugs (ligands). Because of this unique property, alkaloid scaffolds are therefore present in several drugs and lead compounds. This review highlights alkaloid scaffolds in drugs, particularly those recently approved in 2012; it also covers the scaffolds in leads and drug candidates which are in clinical trials and preclinical pipeline. The review focuses on three therapeutic areas including treatments of cancer, tuberculosis, and tobacco cessation. Alkaloid scaffolds in drugs and leads are inspired by those of naturally occurring alkaloids, and these scaffolds include pyridine, piperidine, quinoline, quinolinone, quinazoline, isoquinoline, indole, indolinone, isoindole, isoxazole, imidazole, indazole, thiazole, pyrazole, oxazolidinone, oxadiazole, and benzazepine. In addition to medicinal chemistry aspects, natural products possessing an individual alkaloid scaffold, as well as the mechanism of action of drugs and leads, are also discussed in this review.

  5. A synthetic entry to the tetra cyclic ABDE core of akuammiline alkaloids

    Energy Technology Data Exchange (ETDEWEB)

    Amat, M.; Hadida, S.; Bosch, J. [Laboratory of Organic Chemistry, faculty of Pharmacy, University of Barcelona, Barcelona (Spain)

    1996-08-01

    3-(2-Pyridyl)indole 3a, prepared by Pd(0=-catalyzed cross-coupling of the 3-indolylzinc derivative 1 with halo pyridine 2a), was converted to tetracycle 8.a substructure of akuammiline alkaloids, by a sequence involving the skeletal rearrangement of an intermediate spiroindolenine generated from 1-acyl-2-(3-indolyl)-4-piperidinemethanol mesylate 7 as the crucial step. (Author) 10 refs.

  6. Metabolic effects of the iodothyronine functional analogue TRC150094 on the liver and skeletal muscle of high-fat diet fed overweight rats: an integrated proteomic study.

    Science.gov (United States)

    Silvestri, Elena; Glinni, Daniela; Cioffi, Federica; Moreno, Maria; Lombardi, Assunta; de Lange, Pieter; Senese, Rosalba; Ceccarelli, Michele; Salzano, Anna Maria; Scaloni, Andrea; Lanni, Antonia; Goglia, Fernando

    2012-07-06

    A novel functional iodothyronine analogue, TRC150094, which has a much lower potency toward thyroid hormone receptor (α1/β1) activation than triiodothyronine, has been shown to be effective at reducing adiposity in rats simultaneously receiving a high-fat diet (HFD). Here, by combining metabolic, functional and proteomic analysis, we studied how the hepatic and skeletal muscle phenotypes might respond to TRC150094 treatment in HFD-fed overweight rats. Drug treatment increased both the liver and skeletal muscle mitochondrial oxidative capacities without altering mitochondrial efficiency. Coherently, in terms of individual respiratory in-gel activity, blue-native analysis revealed an increased activity of complex V in the liver and of complexes II and V in tibialis muscle in TCR150094-treated animals. Subsequently, the identification of differentially expressed proteins and the analysis of their interrelations gave an integrated view of the phenotypic/metabolic adaptations occurring in the liver and muscle proteomes during drug treatment. TRC150094 significantly altered the expression of several proteins involved in key liver metabolic pathways, including amino acid and nitrogen metabolism, and fructose and mannose metabolism. The canonical pathways most strongly influenced by TRC150094 in tibialis muscle included glycolysis and gluconeogenesis, amino acid, fructose and mannose metabolism, and cell signaling. The phenotypic/metabolic influence of TRC150094 on the liver and skeletal muscle of HFD-fed overweight rats suggests the potential clinical application of this iodothyronine analogue in ameliorating metabolic risk parameters altered by diet regimens.

  7. Propargylation of Ugi Amide Dianion: An Entry into Pyrrolidinone and Benzoindolizidine Alkaloid Analogues.

    Science.gov (United States)

    Zidan, Alaa; Cordier, Marie; El-Naggar, Abeer M; Abd El-Sattar, Nour E A; Hassan, Mohamed Ali; Ali, Ali Khalil; El Kaïm, Laurent

    2018-05-04

    Propargylation of Ugi adducts under the addition of excess sodium hydride in DMSO leads to direct formation of pyrrolidinone enamides, which are useful precursors of iminium intermediates and may be trapped by various nucleophiles. This approach has been applied to the formation of benzoindolizidine alkaloids with high diversity via a Ugi/propargylation/Pictet-Spengler cyclization.

  8. Indole Alkaloids Inhibiting Neural Stem Cell from Uncaria rhynchophylla.

    Science.gov (United States)

    Wei, Xin; Jiang, Li-Ping; Guo, Ying; Khan, Afsar; Liu, Ya-Ping; Yu, Hao-Fei; Wang, Bei; Ding, Cai-Feng; Zhu, Pei-Feng; Chen, Ying-Ying; Zhao, Yun-Li; Chen, Yong-Bing; Wang, Yi-Fen; Luo, Xiao-Dong

    2017-10-01

    Uncaria rhynchophylla is commonly recognized as a traditional treatment for dizziness, cerebrovascular diseases, and nervous disorders in China. Previously, the neuro-protective activities of the alkaloids from U. rhynchophylla were intensively reported. In current work, three new indole alkaloids (1-3), identified as geissoschizic acid (1), geissoschizic acid N 4 -oxide (2), and 3β-sitsirikine N 4 -oxide (3), as well as 26 known analogues were isolated from U. rhynchophylla. However, in the neural stem cells (NSCs) proliferation assay for all isolated compounds, geissoschizic acid (1), geissoschizic acid N 4 -oxide (2), isocorynoxeine (6), isorhynchophylline (7), (4S)-akuammigine N-oxide (8), and (4S)-rhynchophylline N-oxide (10) showed unexpected inhibitory activities at 10 μM. Unlike previous neuro-protective reports, as a warning or caution, our finding showcased a clue for possible NSCs toxicity and the neural lesions risk of U. rhynchophylla, while the structure-activity relationships of the isolated compounds were discussed also.

  9. Molecular docking study of Papaver alkaloids to some alkaloid receptors

    Directory of Open Access Journals (Sweden)

    A. Nofallah

    2017-11-01

    Full Text Available Background and objectives: More than 40 different alkaloids have been obtained from opium the most important of which are morphine, codeine, papaverine, noscapine and tabaine. Opioid alkaloids produce analgesia by affecting areas of the brain that have peptides with pharmacological pseudo-opioid properties. These alkaloids show important effects on some intracellular peptides like mu, delta, and kappa receptors. Therefore, studying the effects of these alkaloids on different receptors is essential. Methods: Molecular docking is a well-known method in exploring the protein-ligand interactions. In this research, five important alkaloids were docked to crystal structure of human mu opioid receptor (4DKL, human delta opioid receptor (4EJ4 and human kappa opioid receptor (4DJH which were retrieved from protein databank. The 3D-structures of alkaloids were drawn by chembiooffice2010 and minimized with hyperchem package and submitted to molecular docking utilizing autodock-vina. Flexibility of the proteins was considered. The docking studies were performed to compare the affinity of these five alkaloids to the mentioned receptors. Results: We computationally docked each alkaloid compound onto each receptor structure and estimated their binding affinity based on dock scores. Dock score is a criteria including binding energy which utilized here for prediction and comparison of the binding affinities. Binding interactions of the docked alkaloids in receptor pockets were also visually inspected and compared. Conclusion: In this approach, using docking study as a computational method provided a valuable insight of opioid receptor pocket structures which would be essential to design more efficient drugs in pain managements and addiction treatments.

  10. Immunochemical Analysis of Paxilline and Ergot Alkaloid Mycotoxins in Grass Seeds and Plants.

    Science.gov (United States)

    Bauer, Julia I; Gross, Madeleine; Cramer, Benedikt; Humpf, Hans-Ulrich; Hamscher, Gerd; Usleber, Ewald

    2018-01-10

    Limited availability of toxin standards for lolitrem B and ergovaline impedes routine control of grasses for endophyte toxins. This study aimed at assessing the applicability of an enzyme immunoassay (EIA) for the indole-diterpene mycotoxin paxilline, in combination with a generic EIA for ergot alkaloids, as alternative parameters for screening purposes. Analysis of grass seeds and model pastures of four different grass species showed that both EIAs yielded highly positive results for paxilline and ergot alkaloids in perennial ryegrass seeds. Furthermore, evidence for natural occurrence of paxilline in grass in Germany was obtained. High performance liquid chromatography-tandem mass spectrometry analysis qualitatively confirmed the paxilline EIA results but showed that paxilline analogues 1'-O-acetylpaxilline and 13-desoxypaxilline were the predominant compounds in seeds and grass. In the absence of easily accessible reference standards for specific analysis of some major endophyte toxins, analysis of paxilline and ergot alkaloids by EIA may be suitable substitute parameters. The major advantage of this approach is its ease of use and speed, providing an analytical tool which could enhance routine screening for endophyte toxins in pasture.

  11. Synthesis and Evaluation of Febrifugine Analogues as Potential Antimalarial Agents

    OpenAIRE

    Zhu, Shuren; Meng, Li; Zhang, Quan; Wei, Lai

    2006-01-01

    Febrifugine is an alkaloid isolated from Dichroa febrifuga Lour as the active component against Plasmodium falciparum. Strong liver toxicity has precluded febrifugine as a potential clinical drug. In this study novel febrifugine analogues were designed and synthesized. Lower toxicity was achieved by reducing or eliminating the tendency of forming chemically reactive and toxic intermediates and metabolites. Synthesized compounds were evaluated in vitro against chloroquine sensitive (D6) and ch...

  12. Alkaloids from Delphinium pentagynum.

    Science.gov (United States)

    Díaz, Jesús G; Ruiz, Juan García; Herz, Werner

    2004-07-01

    Aerial parts of a collection of Delphinium pentagynum Lam. from Niebla, Southern Spain, furnished one diterpene alkaloid, 2-dehydrodeacetylheterophylloidine, two norditerpene alkaloids, 14-demethyl-14-isobutyrylanhweidelphinine and 14-demethyl-14-acetylanhweidelphinine, the known alkaloids 14-deacetylnudicauline, methyllycaconitine, 14-deacetyl-14-isobutyrylnudicauline, 14-acetylbrowniine, browniine, delcosine, lycoctonine, 18-methoxygadesine, neoline, karakoline and the aporphine alkaloid magnoflorine. Structures of the alkaloids were established by MS, 1D and 2-D NMR techniques.

  13. [Comparative metabolism of three amide alkaloids from Piper longum in five different species of liver microsomes].

    Science.gov (United States)

    He, Huan; Guo, Wei-Wei; Chen, Xiao-Qing; Zhao, Hai-Yu; Wu, Xia

    2016-08-01

    Piperine, piperlonguminine and pellitorine are three major amide alkaloids from Piper longum, showing a variety of pharmacological activities. In order to investigate the different metabolism pathways of these compounds in five species of liver microsomes in vitro, the data of full mass spectrum, and MS2, MS3 spectra of these three alkaloids were collected and analyzed by using ultra-high-performance liquid chromatography coupled with a LTQ-orbitrap mass spectrometer (UHPLC-LTQ-Orbitrap MS); gragment ion information was collected and combined with fragmentation regularities of mass spectra and accurate mass spectrometry data of metabolites, to compare the metabolism difference of three amide alkaloids in liver microsomes of human, rhesus monkey, Beagle dogs, rats and mice. 3 metabolites of piperine, 2 metabolites of piperlonguminine and 1 metabolite of pellitorine were identified quickly. The results showed that the major metabolic pathways of these amide alkaloids in liver microsomes were methylenedioxy group demethylation and oxidation reaction, and metabolic rates were different between species. This study provides basis for further research on in vivo metabolism of piperine analogues from Piper longum. Copyright© by the Chinese Pharmaceutical Association.

  14. Visual identification of alkaloids in some medicinal plants: common alkaloid reagents versus bromocresol green

    Directory of Open Access Journals (Sweden)

    Shamsa F, Esfahani HR, Gamooshi RA

    2008-07-01

    Full Text Available "n Normal 0 false false false MicrosoftInternetExplorer4 /* Style Definitions */ table.MsoNormalTable {mso-style-name:"Table Normal"; mso-tstyle-rowband-size:0; mso-tstyle-colband-size:0; mso-style-noshow:yes; mso-style-parent:""; mso-padding-alt:0cm 5.4pt 0cm 5.4pt; mso-para-margin:0cm; mso-para-margin-bottom:.0001pt; mso-pagination:widow-orphan; font-size:10.0pt; font-family:"Times New Roman"; mso-ansi-language:#0400; mso-fareast-language:#0400; mso-bidi-language:#0400;} Background: Alkaloids are a group of nitrogenous compounds with potential effects on the physiological behavior of human and animals. Some of these compounds are considered important drugs in modern medicine, such as atropine and morphine. Plants are considered the most important source of alkaloids. Therefore, investigating the presence of alkaloids in different plants is very important. Usually, alkaloids in plants are identified by methods such as those of Dragendorf, Wagner and Meyer, among others, which require milligrams of alkaloids for identification. In the present study, a fast and sensitive procedure for detecting of alkaloids in plants is presented.   "n"nMethods: Twelve dried plants samples were investigated for the presence alkaloids. After extracting the total alkaloid into methanol using a Soxhlet extractor, a few milligrams of the extract was transferred to a separatory funnel, buffered to pH 4.7, the bromocresol green (BCG solution (10-4 M was added, mixed and extracted with CHCl3 until a yellow color was observed in the CHCl3 layer, indicating the presence of the alkaloid. The crude extracts were also investigated by the standard methods of Dragendorf, Wagner and Meyer for the presence of alkaloids.   "n"nResults: Investigation of the 12 plant samples for the presence of alkaloids by the standard reagents of Dragendorf, Wagner, and Meyer showed that only Camelia sinensis (flowers, Echium amoenum Fisch & Mey (flowers, and Stachys (aerial parts are devoid

  15. Fluorescence properties of the anti-tumour alkaloid luotonin A and new synthetic analogues: pH modulation as an approach to their fluorimetric quantitation in biological samples

    International Nuclear Information System (INIS)

    González-Ruiz, Víctor; González-Cuevas, Yamisley; Arunachalam, Sankaralingam; Martín, M. Antonia; Olives, Ana I.; Ribelles, Pascual; Ramos, M. Teresa; Menéndez, J. Carlos

    2012-01-01

    Luotonin A is an alkaloid structurally related to the natural anti-tumour agent camptothecin. The fluorescence behaviour of luotonin A and a series of six analogues is described in the present work. The influence of solvent polarity and pH on the native fluorescence properties of these alkaloids was studied, finding that in organic solvents or in aqueous solutions (pH 5.5–7.2) the neutral form of the luotonin derivatives emit in the region of 410–450 nm but, in both media, acidification to pH values below 3.0 causes a new emission band to appear at about 500 nm. An ESPT reaction occurs due to the protonation of the basic nitrogen atoms of the pentacyclic ring. Acid-base titrations of luotonin A and its derivatives in aqueous and acetonitrile media were carried out in order to determine their pK a ⁎ values which were around 2, showing these compounds to be very weak bases. In aqueous media, the absence of an iso-emissive point in the emission spectra suggests the existence of more than two species in the proton transfer equilibria. The basicity of the luotonin A derivatives is increased in organic media, and a good correlation between the pK a ⁎ values and the chemical structure was found. The protonation of luotonin A was also studied by 1 H-NMR and 13 C-NMR experiments, which proved the protonation of the nitrogen atoms at the positions 5 and 6 of the pentacyclic ring. The fluorescence quantum yields were determined in ethanol and in aqueous solutions under neutral and acidic conditions. The fluorescence quantum yields were higher in water for the case of the more polar compounds, and the opposite result was obtained for the more hydrophobic ones. The remarkable and interesting fluorescence properties of luotonin A prompted the development of its fluorimetric analytical quantitation, obtaining very good analytical features. - Highlights: ► This is the first study on the fluorescence properties of luotonin A analogues. ► Fluorescence and NMR experiments

  16. Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine.

    Science.gov (United States)

    Colegate, Steven M; Gardner, Dale R; Betz, Joseph M; Panter, Kip E

    2014-01-01

    The diversity of structure and, particularly, stereochemical variation of the dehydropyrrolizidine alkaloids can present challenges for analysis and the isolation of pure compounds for the preparation of analytical standards and for toxicology studies. To investigate methods for the separation of gram-scale quantities of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine and to compare their NMR spectroscopic data with those of their heliotridine-based analogues echinatine and rinderine. Lycopsamine and intermedine were extracted, predominantly as their N-oxides and along with their acetylated derivatives, from commercial samples of comfrey (Symphytum officinale) root. Alkaloid enrichment involved liquid-liquid partitioning of the crude methanol extract between dilute aqueous acid and n-butanol, reduction of N-oxides and subsequent continuous liquid-liquid extraction of free base alkaloids into CHCl3 . The alkaloid-rich fraction was further subjected to semi-automated flash chromatography using boronated soda glass beads or boronated quartz sand. Boronated soda glass beads (or quartz sand) chromatography adapted to a Biotage Isolera Flash Chromatography System enabled large-scale separation (at least up to 1-2 g quantities) of lycopsamine and intermedine. The structures were confirmed using one- and two-dimensional (1) H- and (13) C-NMR spectroscopy. Examination of the NMR data for lycopsamine, intermedine and their heliotridine-based analogues echinatine and rinderine allowed for some amendments of literature data and provided useful comparisons for determining relative configurations in monoester dehydropyrrolizidine alkaloids. A similar NMR comparison of lycopsamine and intermedine with their N-oxides showed the effects of N-oxidation on some key chemical shifts. A levorotatory shift in specific rotation from +3.29° to -1.5° was observed for lycopsamine when dissolved in ethanol or methanol respectively. A semi-automated flash

  17. Fluorescence properties of the anti-tumour alkaloid luotonin A and new synthetic analogues: pH modulation as an approach to their fluorimetric quantitation in biological samples

    Energy Technology Data Exchange (ETDEWEB)

    Gonzalez-Ruiz, Victor; Gonzalez-Cuevas, Yamisley; Arunachalam, Sankaralingam [S. D. Quimica Analitica, Facultad de Farmacia, Universidad Complutense de Madrid, 28040-Madrid (Spain); Martin, M. Antonia, E-mail: mantonia@farm.ucm.es [S. D. Quimica Analitica, Facultad de Farmacia, Universidad Complutense de Madrid, 28040-Madrid (Spain); Olives, Ana I. [S. D. Quimica Analitica, Facultad de Farmacia, Universidad Complutense de Madrid, 28040-Madrid (Spain); Ribelles, Pascual; Ramos, M. Teresa; Menendez, J. Carlos [D. Quimica Organica y Farmaceutica, Facultad de Farmacia, Universidad Complutense de Madrid, 28040-Madrid (Spain)

    2012-09-15

    Luotonin A is an alkaloid structurally related to the natural anti-tumour agent camptothecin. The fluorescence behaviour of luotonin A and a series of six analogues is described in the present work. The influence of solvent polarity and pH on the native fluorescence properties of these alkaloids was studied, finding that in organic solvents or in aqueous solutions (pH 5.5-7.2) the neutral form of the luotonin derivatives emit in the region of 410-450 nm but, in both media, acidification to pH values below 3.0 causes a new emission band to appear at about 500 nm. An ESPT reaction occurs due to the protonation of the basic nitrogen atoms of the pentacyclic ring. Acid-base titrations of luotonin A and its derivatives in aqueous and acetonitrile media were carried out in order to determine their pK{sub a}{sup Low-Asterisk} values which were around 2, showing these compounds to be very weak bases. In aqueous media, the absence of an iso-emissive point in the emission spectra suggests the existence of more than two species in the proton transfer equilibria. The basicity of the luotonin A derivatives is increased in organic media, and a good correlation between the pK{sub a}{sup Low-Asterisk} values and the chemical structure was found. The protonation of luotonin A was also studied by {sup 1}H-NMR and {sup 13}C-NMR experiments, which proved the protonation of the nitrogen atoms at the positions 5 and 6 of the pentacyclic ring. The fluorescence quantum yields were determined in ethanol and in aqueous solutions under neutral and acidic conditions. The fluorescence quantum yields were higher in water for the case of the more polar compounds, and the opposite result was obtained for the more hydrophobic ones. The remarkable and interesting fluorescence properties of luotonin A prompted the development of its fluorimetric analytical quantitation, obtaining very good analytical features. - Highlights: Black-Right-Pointing-Pointer This is the first study on the fluorescence

  18. A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin

    Directory of Open Access Journals (Sweden)

    Gianfranco Favi

    2013-02-01

    Full Text Available A series of substituted ethyl 1-[(tert-butoxycarbonylamino]-2-methyl-5- (1-methyl-1H-indol-3-yl-4-[(1-methyl-1H-indol-3-ylcarbonyl]-1H-pyrrole-3-carboxylates were prepared in excellent yields (82-98% by one-pot reactions between β-dicarbonyl compounds 12a–e and 1,2-diaza-1,3-diene (DD 13. Derivatives 10a,c–e, deazaanalogues of the bis-indole alkaloid topsentin, screened by the National Cancer Institute (Bethesda, MD, USA in the in vitro one dose primary anticancer assay against a panel of about 60 human tumor cell lines, showed no significant activity, with the exception of compound 9e, which showed moderate activity against the HOP-92 cell line of the non small cell lung cancer sub-panel and the SNB-75 cell line of the CNS sub-panel.

  19. Inhibitive action of alkaloids and non alkaloid fractions of the ...

    African Journals Online (AJOL)

    The corrosion inhibition of mild steel in 2.0 MHCl solution by non-alkaloidal and alkaloidal fractions of the extracts of Phyllanthus amarus (NAEPA and AEPA respectively) was studied using gravimetric and gasometric techniques at 303 and 323 K. The results revealed that the extracts functioned as good corrosion inhibitors.

  20. Synthesis of bicyclic alkaloids from the iridoid antirrhinoside

    DEFF Research Database (Denmark)

    Frederiksen, Signe Maria

    The present thesis describes the isolation of the iridoid glucoside antirrhinoside from Antirrhinum majus, and the approaches made towards its transformation into analogues of biologically active compounds, with special interest in syntheses of bicyclic alkaloids.A synthetic piperidine monoterpene...... or by reduction using lithium aluminum hydride. The piperidines were subjected to hydrogenation to remove the N-benzyl group. The compounds were tested for hypoglycaemic activity by Novo Nordisk, but no activity was observed.Another approach towards a synthetic piperidine monoterpene was attempted. The strategy...... involved preparation of a diol, which through treatment of its ditosyl derivative with an amine would afford a piperidine monoterpene. Antirrhinoside was protected as its 5,6-O-monoacetonide via its 5,6:4',6'-O-diacetonide. The 5,6-O-isopropylidene-derivative was hydrogenated to give the 3,4-dihydro...

  1. Catharanthus alkaloids XXXII: isolation of alkaloids from Catharanthus trichophyllus roots and structure elucidation of cathaphylline.

    Science.gov (United States)

    Cordell, G A; Farnsworth, N R

    1976-03-01

    Further examination of the cytotoxic alkaloid fractions of Catharanthus trichophyllus roots afforded nine alkaloids. Two of these alkaloids, lochnericine and horhammericine, are responsible for part of the cytotoxic activity. The structure elucidation of cathaphylline, a new beta-anilino acrylate derivative, is described.

  2. Dietary alkaloid sequestration in a poison frog: an experimental test of alkaloid uptake in Melanophryniscus stelzneri (Bufonidae).

    Science.gov (United States)

    Hantak, Maggie M; Grant, Taran; Reinsch, Sherri; McGinnity, Dale; Loring, Marjorie; Toyooka, Naoki; Saporito, Ralph A

    2013-12-01

    Several lineages of brightly colored anurans independently evolved the ability to secrete alkaloid-containing defensive chemicals from granular glands in the skin. These species, collectively referred to as 'poison frogs,' form a polyphyletic assemblage that includes some species of Dendrobatidae, Mantellidae, Myobatrachidae, Bufonidae, and Eleutherodactylidae. The ability to sequester alkaloids from dietary arthropods has been demonstrated experimentally in most poison frog lineages but not in bufonid or eleutherodactylid poison frogs. As with other poison frogs, species of the genus Melanophryniscus (Bufonidae) consume large numbers of mites and ants, suggesting they might also sequester defensive alkaloids from dietary sources. To test this hypothesis, fruit flies dusted with alkaloid/nutritional supplement powder were fed to individual Melanophryniscus stelzneri in two experiments. In the first experiment, the alkaloids 5,8-disubstituted indolizidine 235B' and decahydroquinoline were administered to three individuals for 104 days. In the second experiment, the alkaloids 3,5-disubstituted indolizidine 239Q and decahydroquinoline were given to three frogs for 153 days. Control frogs were fed fruit flies dusted only with nutritional supplement. Gas chromatography/mass spectrometry analyses revealed that skin secretions of all experimental frogs contained alkaloids, whereas those of all control frogs lacked alkaloids. Uptake of decahydroquinoline was greater than uptake of 5,8-disubstituted indolizidine, and uptake of 3,5-disubstituted indolizidine was greater than uptake of decahydroquinoline, suggesting greater uptake efficiency of certain alkaloids. Frogs in the second experiment accumulated a greater amount of alkaloid, which corresponds to the longer duration and greater number of alkaloid-dusted fruit flies that were consumed. These findings provide the first experimental evidence that bufonid poison frogs sequester alkaloid-based defenses from dietary

  3. RIA for indol alkaloids

    International Nuclear Information System (INIS)

    Arens, H.

    1979-01-01

    The technique of RIAs for indol alkaloids (ajmaline, ergotamine, ergocristine, ergometrine, and lysergic acid) is described, and applications for this RIA and the RIA for raubasine and serpentine are mentioned. The indol alkaloide RIAs are shown to be suitable both for alkaloid distribution measurements in Catharantus and Rauwolfia plants and C. purpurea sclerotia as well as for the selection of high-efficiency strains and the optimisation of cultures of plant tissues and saprophytic fungi. (orig./MG) [de

  4. Bioactive alkaloids from marine sponges

    Digital Repository Service at National Institute of Oceanography (India)

    Singh, K.S.; Majik, M.S.

    lines while kuanoniamine C was less potent but showed high selectivity toward the estrogen dependent breast cancer cell line (Kijjoa et. al., 2007). Recently, Davis’s and coworkers, reported two new cytotoxici- ty peridoacridine alkaloids viz... 10 sponge, Trachycladus laevispirulifer. Excitingly, it displayed promising selective cytotoxicity against a panel of human cancer cell lines. 12.3.1. BISINDOLE ALKALOIDS Bis-indole alkaloids, consisting of two indole moieties...

  5. Ergot alkaloid transport across ruminant gastric tissues.

    Science.gov (United States)

    Hill, N S; Thompson, F N; Stuedemann, J A; Rottinghaus, G W; Ju, H J; Dawe, D L; Hiatt, E E

    2001-02-01

    Ergot alkaloids cause fescue toxicosis when livestock graze endophyte-infected tall fescue. It is generally accepted that ergovaline is the toxic component of endophyte-infected tall fescue, but there is no direct evidence to support this hypothesis. The objective of this study was to examine relative and potential transport of ergoline and ergopeptine alkaloids across isolated gastric tissues in vitro. Sheep ruminal and omasal tissues were surgically removed and placed in parabiotic chambers. Equimolar concentrations of lysergic acid, lysergol, ergonovine, ergotamine, and ergocryptine were added to a Kreb's Ringer phosphate (KRP) solution on the mucosal side of the tissue. Tissue was incubated in near-physiological conditions for 240 min. Samples were taken from KRP on the serosal side of the chambers at times 0, 30, 60, 120, 180, and 240 min and analyzed for ergot alkaloids by competitive ELISA. The serosal KRP remaining after incubation was freeze-dried and the alkaloid species quantified by HPLC. The area of ruminal and omasal tissues was measured and the potential transportable alkaloids calculated by multiplying the moles of transported alkaloids per square centimeter of each tissue type by the surface area of the tissue. Studies were conducted to compare alkaloid transport in reticular, ruminal, and omasal tissues and to determine whether transport was active or passive. Ruminal tissue had greater ergot alkaloid transport potential than omasal tissue (85 vs 60 mmol) because of a larger surface area. The ruminal posterior dorsal sac had the greatest potential for alkaloid transport, but the other ruminal tissues were not different from one another. Alkaloid transport was less among reticular tissues than among ruminal tissues. Transport of alkaloids seemed to be an active process. The alkaloids with greatest transport potential were lysergic acid and lysergol. Ergopeptine alkaloids tended to pass across omasal tissues in greater quantities than across ruminal

  6. Effects of Supplementation of Alkaloid and Non Alkaloid from Sauropus androgynus Leaves on Egg Production and Lipid Profil in Layer Chicken

    Directory of Open Access Journals (Sweden)

    U Santoso

    2010-09-01

    Full Text Available The present study was conducted to evaluate effects of supplementation of alkaloid or non alkaloid from Sauropus androgynus leaves on productive performance and the contents of lipid fractions in layer chickens. Forty two layer chickens aged 30 weeks were distributed to seven treatment groups. Each treatment group contained six layer chickens maintained in an individual cage, respectively. The present experiment used completely randomized experimental design. The seven treatment groups were as follows: 1 Control, layer chickens were fed diet without supplementation of alkaloid or non alkaloid extracted from Sauropus androgynus (P0; 2 Layer chickens were fed diet contained 30 mg non alkaloid/kg diet (P1; 3 Layer chickens were fed diet contained 60 mg non alkaloid/kg diet (P2; 4 Layer chickens were fed diet contained 90 mg non alkaloid/kg diet (P3; 5 Layer chickens were fed diet contained 30 mg alkaloid/kg diet (P4; 6 Layer chickens were fed diet contained 60 mg alkaloid/kg diet (P5; 7 Layer chickens were fed diet contained 90 mg alkaloid/kg diet (P6. Layer chickens were fed experimental diet with 2,750 kcal/kg Metabolizable Energy (ME and 16.0% protein. Diet and drinking water were fed ad libitum. Experimental results showed that supplementation of alkaloid or non alkaloid from Sauropus androgynus leaves significantly affected productive performance in layer chickens. It appear that non alkaloid supplementation had no advantage in improving productive performance, whereas supplementation of 30 mg alkaloid/kg diet might have advantages in improving productive performance as indicated by better egg production and lower feed conversion ratio. Treatment had no effect on glucose and triglyceride concentration in serum, but it affected total cholesterol, HDL-cholesterol, LDL+VLDL-cholesterol and atherogenic index in serum. Cholesterol concentration in serum was significantly increased in P4 and P6, whereas HDL-cholesterol concentration was

  7. Genotoxic effect of alkaloids

    Directory of Open Access Journals (Sweden)

    J. A. P. Henriques

    1991-01-01

    Full Text Available Because of the increase use of alkaloids in general medical practice in recent years, it is of interest to determine genotoxic, mutagenic and recombinogenic response to different groups of alkaloids in prokaryotic and eucaryotic organisms. Reserpine, boldine and chelerythrine did not show genotoxicity response in the SOS-Chromotest whereas skimmianine showed genotixicity in the presence of a metabolic activation mixture. Voacristine isolated fromthe leaves of Ervatamia coronaria shows in vivo cytostatic and mutagenic effects in Saccharomyces cerevisiae hapioids cells. The Rauwolfia alkaloid (reserpine was not able to induce reverse mutation and recombinational mitotic events (crossing-over and gene conversion in yeast diploid strain XS2316.

  8. Naturally Inspired Peptide Leads: Alanine Scanning Reveals an Actin-Targeting Thiazole Analogue of Bisebromoamide.

    Science.gov (United States)

    Johnston, Heather J; Boys, Sarah K; Makda, Ashraff; Carragher, Neil O; Hulme, Alison N

    2016-09-02

    Systematic alanine scanning of the linear peptide bisebromoamide (BBA), isolated from a marine cyanobacterium, was enabled by solid-phase peptide synthesis of thiazole analogues. The analogues have comparable cytotoxicity (nanomolar) to that of BBA, and cellular morphology assays indicated that they target the actin cytoskeleton. Pathway inhibition in human colon tumour (HCT116) cells was explored by reverse phase protein array (RPPA) analysis, which showed a dose-dependent response in IRS-1 expression. Alanine scanning reveals a structural dependence to the cytotoxicity, actin targeting and pathway inhibition, and allows a new readily synthesised lead to be proposed. © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

  9. Alkaloids from Mongolian species Berberis sibirica Pall

    International Nuclear Information System (INIS)

    Istatkova, R.; Philipov, S.; Tuleva, P.; Amgalan, A.; Samdan, J.; Dangaa, S.

    2007-01-01

    From the aerial parts of Berberis sibirica Pall. 6 isoquinoline alkaloids of protoberberine, protopine, benzphenanthridine and proaporphine type were isolated. The known alkaloids (-)-tetrahydropseudocoptisine, pseudoprotopine, (+)-chelidonine and (+)-glaziovine are new for the family Berberidaceae. From the roots of B. sibirica 10 isoquinoline alkaloids of protoberberine, benzylisoquinoline, bisbenzylisoquinoline, aporphine-benzylisoquinoline and proaporphine-benzylisoquinoline type were isolated. 1,10-Di-O-methylpakistanine has been reported for the first time as a natural alkaloid. The known alkaloids (-)-isothalidezine and (+)-armepavine have been found for the first time in the family Berberidaceae. All structures were determined by physical and spectral data. (authors)

  10. Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity.

    Science.gov (United States)

    Xia, Qingsu; Zhao, Yuewei; Von Tungeln, Linda S; Doerge, Daniel R; Lin, Ge; Cai, Lining; Fu, Peter P

    2013-09-16

    Pyrrolizidine alkaloid-containing plants are the most common poisonous plants affecting livestock, wildlife, and humans. The U.S. National Toxicology Program (NTP) classified riddelliine, a tumorigenic pyrrolizidine alkaloid, as "reasonably anticipated to be a human carcinogen" in the NTP 12th Report on Carcinogens in 2011. We previously determined that four DNA adducts were formed in rats dosed with riddelliine. The structures of the four DNA adducts were elucidated as (i) a pair of epimers of 7-hydroxy-9-(deoxyguanosin-N(2)-yl)dehydrosupinidine adducts (termed as DHP-dG-3 and DHP-dG-4) as the predominant adducts; and (ii) a pair of epimers of 7-hydroxy-9-(deoxyadenosin-N(6)-yl)dehydrosupinidine adducts (termed as DHP-dA-3 and DHP-dA-4 adducts). In this study, we selected a nontumorigenic pyrrolizidine alkaloid, platyphylliine, a pyrrolizidine alkaloid N-oxide, riddelliine N-oxide, and nine tumorigenic pyrrolizidine alkaloids (riddelliine, retrorsine, monocrotaline, lycopsamine, retronecine, lasiocarpine, heliotrine, clivorine, and senkirkine) for study in animals. Seven of the nine tumorigenic pyrrolizidine alkaloids, with the exception of lycopsamine and retronecine, are liver carcinogens. At 8-10 weeks of age, female F344 rats were orally gavaged for 3 consecutive days with 4.5 and 24 μmol/kg body weight test article in 0.5 mL of 10% DMSO in water. Twenty-four hours after the last dose, the rats were sacrificed, livers were removed, and liver DNA was isolated for DNA adduct analysis. DHP-dG-3, DHP-dG-4, DHP-dA-3, and DHP-dA-4 adducts were formed in the liver of rats treated with the individual seven hepatocarcinogenic pyrrolizidine alkaloids and riddelliine N-oxide. These DNA adducts were not formed in the liver of rats administered retronecine, the nontumorigenic pyrrolizidine alkaloid, platyphylliine, or vehicle control. These results indicate that this set of DNA adducts, DHP-dG-3, DHP-dG-4, DHP-dA-3, and DHP-dA-4, is a common biological biomarker of

  11. Alkaloids as Cyclooxygenase Inhibitors in Anticancer Drug Discovery.

    Science.gov (United States)

    Hashmi, Muhammad Ali; Khan, Afsar; Farooq, Umar; Khan, Sehroon

    2018-01-01

    Cancer is the leading cause of death worldwide and anticancer drug discovery is a very hot area of research at present. There are various factors which control and affect cancer, out of which enzymes like cyclooxygenase-2 (COX-2) play a vital role in the growth of tumor cells. Inhibition of this enzyme is a very useful target for the prevention of various types of cancers. Alkaloids are a diverse group of naturally occurring compounds which have shown great COX-2 inhibitory activity both in vitro and in vivo. In this mini-review, we have discussed different alkaloids with COX-2 inhibitory activities and anticancer potential which may act as leads in modern anticancer drug discovery. Different classes of alkaloids including isoquinoline alkaloids, indole alkaloids, piperidine alkaloids, quinazoline alkaloids, and various miscellaneous alkaloids obtained from natural sources have been discussed in detail in this review. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  12. Tulongicin, an Antibacterial Tri-Indole Alkaloid from a Deep-Water Topsentia sp. Sponge.

    Science.gov (United States)

    Liu, Hong-Bing; Lauro, Gianluigi; O'Connor, Robert D; Lohith, Katheryn; Kelly, Michelle; Colin, Patrick; Bifulco, Giuseppe; Bewley, Carole A

    2017-09-22

    Antibacterial-guided fractionation of an extract of a deep-water Topsentia sp. marine sponge led to the isolation of two new indole alkaloids, tulongicin A (1) and dihydrospongotine C (2), along with two known analogues, spongotine C (3) and dibromodeoxytopsentin (4). Their planar structures were determined by NMR spectroscopy. Their absolute configurations were determined through a combination of experimental and computational analyses. Tulongicin (1) is the first natural product to contain a di(6-Br-1H-indol-3-yl)methyl group linked to an imidazole core. The coexistence of tri-indole 1 and bis-indole alcohol 2 suggests a possible route to 1. All of the compounds showed strong antimicrobial activity against Staphylococcus aureus.

  13. ALKALOIDAL COMPOSITION AND TOXICITY STUDIES OF THREE ...

    African Journals Online (AJOL)

    Mattock's test for unsaturated pyrrolizidine alkaloids (hepatotoxic) revealed that only C. retusa contained these alkaloids amongst the three species. This indicated that this is a potentially toxic specie. The alkaloids of C. retusa were toxic to albino (Wistar) rats. Marked microscopic lesions were found, principally in the liver.

  14. Congenital skeletal malformations and cleft palate induced in goats by ingestion of Lupinus, Conium and Nicotiana species.

    Science.gov (United States)

    Panter, K E; Keeler, R F; Bunch, T D; Callan, R J

    1990-01-01

    Three piperidine alkaloid containing plants, Conium maculatum (poison-hemlock), Nicotiana glauca (tree tobacco) and Lupinus formosus (lunara lupine), induced multiple congenital contractures (MCC) and palatoschisis in goat kids when their dams were gavaged with the plant during gestation days 30-60. The skeletal abnormalities included fixed extension or flexure of the carpal, tarsal, and fetlock joints, scoliosis, lordosis, torticollis and rib cage abnormalities. Clinical signs of toxicity included those reported in sheep, cattle and pigs--ataxia, incoordination, muscular weakness, prostration and death. One quinolizidine alkaloid containing plant, Lupinus caudatus (tailcup lupine), on the other hand, which is also known to cause MCC in cows, caused only slight signs of toxicity in pregnant goats and no teratogenic effects in their offspring.

  15. Alkaloids in the pharmaceutical industry: Structure, isolation and application

    Directory of Open Access Journals (Sweden)

    Nikolić Milan

    2003-01-01

    Full Text Available By the end of the 18th and the beginning of the 19th century a new era began in medicine, pharmaceutics and chemistry that was strongly connected with alkaloids and alkaloid drugs. Even before that it was known that certain drugs administered in limited doses were medicines, and toxic if taken in larger doses (opium, coke leaves, belladonna roots, monkshood tubers crocus or hemlock seeds. However, the identification, isolation and structural characterization of the active ingredients of the alkaloid drugs was only possible in the mid 20th century by the use of modern extraction equipment and instrumental methods (NMR, X-ray diffraction and others.In spite of continuing use over a long time, there is still great interest in investigating new drugs, potential raw materials for the pharmaceutical industry, as well as the more detailed investigation and definition of bio-active components and the indication of their activity range, and the partial synthesis of new alkaloid molecules based on natural alkaloids. The scope of these investigations, especially in the field of semi-synthesis is to make better use of the bio-active ingredients of alkaloid drugs, i.e. to improve the pharmacological effect (stronger and prolonged effect of the medicine, decreased toxicity and side effects, or to extend or change the applications. A combined classification of alkaloids was used, based on the chemical structure and origin, i.e. the source of their isolation to study alkaloid structure. For practical reasons, the following classification of alkaloids was used: ergot alkaloids, poppy alkaloids, tropanic alkaloids purine derivative alkaloids, carbon-cyclic alkaloids, and other alkaloids. The second part of this report presents a table of general procedures for alkaloid isolation from plant drugs (extraction by water non-miscible solvents, extraction by water-miscible solvents and extraction by diluted acid solutions. Also, methods for obtaining chelidonine and

  16. Biosynthetic Pathways of Ergot Alkaloids

    Directory of Open Access Journals (Sweden)

    Nina Gerhards

    2014-12-01

    Full Text Available Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines. All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine. Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes.

  17. Piperidine alkaloids: human and food animal teratogens.

    Science.gov (United States)

    Green, Benedict T; Lee, Stephen T; Panter, Kip E; Brown, David R

    2012-06-01

    Piperidine alkaloids are acutely toxic to adult livestock species and produce musculoskeletal deformities in neonatal animals. These teratogenic effects include multiple congenital contracture (MCC) deformities and cleft palate in cattle, pigs, sheep, and goats. Poisonous plants containing teratogenic piperidine alkaloids include poison hemlock (Conium maculatum), lupine (Lupinus spp.), and tobacco (Nicotiana tabacum) [including wild tree tobacco (Nicotiana glauca)]. There is abundant epidemiological evidence in humans that link maternal tobacco use with a high incidence of oral clefting in newborns; this association may be partly attributable to the presence of piperidine alkaloids in tobacco products. In this review, we summarize the evidence for piperidine alkaloids that act as teratogens in livestock, piperidine alkaloid structure-activity relationships and their potential implications for human health. Copyright © 2012 Elsevier Ltd. All rights reserved.

  18. Novel synthetic organic compounds inspired from antifeedant marine alkaloids as potent bacterial biofilm inhibitors.

    Science.gov (United States)

    Rane, Rajesh A; Karpoormath, Rajshekhar; Naphade, Shital S; Bangalore, Pavankumar; Shaikh, Mahamadhanif; Hampannavar, Girish

    2015-08-01

    In this paper, we have reported seventeen novel synthetic organic compounds derived from marine bromopyrrole alkaloids, exhibiting potential inhibition of biofilm produced by Gram-positive bacteria. Compound 5f with minimumbiofilm inhibitory concentration(MBIC) of 0.39, 0.78 and 3.125 μg/mL against MSSA, MRSA and SE respectively, emerged as promising anti-biofilm lead compounds. In addition, compounds 5b, 5c, 5d, 5e, 5f, 5h, 5i and 5j revealed equal potency as that of the standard drug Vancomycin (MBIC = 3.125 μg/mL) against Streptococcus epidermidis. Notably, most of the synthesized compounds displayed better potency than Vancomycin indicating their potential as inhibitors of bacterial biofilm. The cell viability assay for the most active hybrid confirms its anti-virulence properties which need to be further researched. Copyright © 2015 Elsevier Inc. All rights reserved.

  19. Four alkaloids from Annona cherimola.

    Science.gov (United States)

    Chen, C Y; Chang, F R; Pan, W B; Wu, Y C

    2001-04-01

    Four alkaloids, annocherine A, annocherine B, cherianoine, and romucosine H, along with one known alkaloid, artabonatine B, were isolated from the MeOH extract of the stems of Annona cherimola. Their structures were identified on the basis of both analysis of their spectral data and from chemical evidence.

  20. Manipulating lightcone fluctuations in an analogue cosmic string

    Directory of Open Access Journals (Sweden)

    Jiawei Hu

    2018-02-01

    Full Text Available We study the flight time fluctuations in an anisotropic medium inspired by a cosmic string with an effective fluctuating refractive index caused by fluctuating vacuum electric fields, which are analogous to the lightcone fluctuations due to fluctuating spacetime metric when gravity is quantized. The medium can be realized as a metamaterial that mimics a cosmic string in the sense of transformation optics. For a probe light close to the analogue string, the flight time variance is ν times that in a normal homogeneous and isotropic medium, where ν is a parameter characterizing the deficit angle of the spacetime of a cosmic string. The parameter ν, which is always greater than unity for a real cosmic string, is determined by the dielectric properties of the metamaterial for an analogue string. Therefore, the flight time fluctuations of a probe light can be manipulated by changing the electric permittivity and magnetic permeability of the analogue medium. We argue that it seems possible to fabricate a metamaterial that mimics a cosmic string with a large ν in laboratory so that a currently observable flight time variance might be achieved.

  1. Manipulating lightcone fluctuations in an analogue cosmic string

    Science.gov (United States)

    Hu, Jiawei; Yu, Hongwei

    2018-02-01

    We study the flight time fluctuations in an anisotropic medium inspired by a cosmic string with an effective fluctuating refractive index caused by fluctuating vacuum electric fields, which are analogous to the lightcone fluctuations due to fluctuating spacetime metric when gravity is quantized. The medium can be realized as a metamaterial that mimics a cosmic string in the sense of transformation optics. For a probe light close to the analogue string, the flight time variance is ν times that in a normal homogeneous and isotropic medium, where ν is a parameter characterizing the deficit angle of the spacetime of a cosmic string. The parameter ν, which is always greater than unity for a real cosmic string, is determined by the dielectric properties of the metamaterial for an analogue string. Therefore, the flight time fluctuations of a probe light can be manipulated by changing the electric permittivity and magnetic permeability of the analogue medium. We argue that it seems possible to fabricate a metamaterial that mimics a cosmic string with a large ν in laboratory so that a currently observable flight time variance might be achieved.

  2. Selective reduction of peptidic ergot alkaloids

    Czech Academy of Sciences Publication Activity Database

    Cvak, L.; Stuchlík, J.; Schreiberová, M.; Sedmera, Petr; Havlíček, Vladimír; Flieger, Miroslav; Čejka, J.; Kratochvíl, B.; Jegorov, A.

    2000-01-01

    Roč. 65, - (2000), s. 1762-1776 ISSN 0010-0765 Institutional research plan: CEZ:AV0Z5020903 Keywords : indole alkaloids * ergot alkaloids * ergopeptides Subject RIV: EE - Microbiology, Virology Impact factor: 0.960, year: 2000

  3. Congenital skeletal malformations induced by maternal ingestion of Conium maculatum (poison hemlock) in newborn pigs.

    Science.gov (United States)

    Panter, K E; Keeler, R F; Buck, W B

    1985-10-01

    Skeletal malformations were induced in newborn pigs from gilts fed Conium maculatum seed or plant during gestation days 43 through 53 and 51 through 61. The teratogenic effects in groups dosed during gestation days 43 through 53 were more severe than those in groups dosed during the later period, with many newborn pigs showing arthrogryposis and twisted and malaligned bones in the limbs and with 1 pig showing scoliosis and deformity of the thoracic cage. The pigs born to gilts given C maculatum during gestation days 51 through 61 had excessive flexure primarily in the carpal joints, without scoliosis or bone malalignment in the limbs. The teratogenicity of poison hemlock depends on the alkaloid concentration and content. Based on the data presented, we speculate that gamma-coniceine is the teratogenic alkaloid in the poison hemlock fed to the gilts.

  4. Alkaloids from Isopyrum thalictroides L.

    Science.gov (United States)

    Istatkova, Ralitsa; Philipov, Stefan

    2004-06-01

    Two new aporphine-benzylisoquinoline alkaloids thaliphine and isothaliphine with a new type of ether bridge were isolated from the roots and rhyzomes of Isopyrum thalictroides L. (Ranunculaceae). Their structures were established by physical and spectral analysis. The known alkaloid N-methylglaucine was isolated for the first time from a plant of the family Ranunculaceae.

  5. Benzylisoquinoline alkaloid biosynthesis in opium poppy.

    Science.gov (United States)

    Beaudoin, Guillaume A W; Facchini, Peter J

    2014-07-01

    Opium poppy (Papaver somniferum) is one of the world's oldest medicinal plants and remains the only commercial source for the narcotic analgesics morphine, codeine and semi-synthetic derivatives such as oxycodone and naltrexone. The plant also produces several other benzylisoquinoline alkaloids with potent pharmacological properties including the vasodilator papaverine, the cough suppressant and potential anticancer drug noscapine and the antimicrobial agent sanguinarine. Opium poppy has served as a model system to investigate the biosynthesis of benzylisoquinoline alkaloids in plants. The application of biochemical and functional genomics has resulted in a recent surge in the discovery of biosynthetic genes involved in the formation of major benzylisoquinoline alkaloids in opium poppy. The availability of extensive biochemical genetic tools and information pertaining to benzylisoquinoline alkaloid metabolism is facilitating the study of a wide range of phenomena including the structural biology of novel catalysts, the genomic organization of biosynthetic genes, the cellular and sub-cellular localization of biosynthetic enzymes and a variety of biotechnological applications. In this review, we highlight recent developments and summarize the frontiers of knowledge regarding the biochemistry, cellular biology and biotechnology of benzylisoquinoline alkaloid biosynthesis in opium poppy.

  6. Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agents.

    Science.gov (United States)

    Zhu, Shuren; Zhang, Quan; Gudise, Chandrashekar; Wei, Lai; Smith, Erika; Zeng, Yuling

    2009-07-01

    Febrifugine is an alkaloid isolated from Dichroa febrifuga Lour as the active component against Plasmodium falciparum. Adverse side effects have precluded febrifugine as a potential clinical drug. In this study novel febrifugine analogues were designed and synthesized. Lower toxicity was achieved by reducing or eliminating the tendency of forming chemically reactive and toxic intermediates and metabolites. Synthesized compounds were evaluated for acute toxicity and in vitro and in vivo antimalarial efficacy. Some compounds are much less toxic than the natural product febrifugine and existing antimalarial drug chloroquine and are expected to possess wide therapeutic windows. These compounds, as well as the underlying design rationale, may find usefulness in the discovery and development of new antimalarial drugs.

  7. TOXIC PYRROLIZIDINE ALKALOIDS OF ECHIUM AMOENUM FISCH. & MEY.

    Directory of Open Access Journals (Sweden)

    MITRA MEHRABANI

    2006-06-01

    Full Text Available Toxic pyrrolizidine alkaloids are present in some species of Echium (Boraginaceae. In this study petals of Echium amoenum Fisch. & Mey. (Gol-e-Gavzaban as a popular herbal medicine in Iran, were investigated for pyrrolizidine alkaloids (PAs. The alkaloids were separated and purified by preparative TLC and characterized by IR, one and two dimensional 1H and 13C-NMR and Mass spectroscopy. Four toxic alkaloids namely: echimidine I, echimidine isomer II, 7-angeloyl retronecine III and 7-tigloyl retronecine IV were identified.

  8. Alkaloids from single skins of the Argentinian toad Melanophryniscus rubriventris (ANURA, BUFONIDAE): An unexpected variability in alkaloid profiles and a profusion of new structures.

    Science.gov (United States)

    Garraffo, H Martin; Andriamaharavo, Nirina R; Vaira, Marcos; Quiroga, María F; Heit, Cecilia; Spande, Thomas F

    2012-12-01

    GC-MS analysis of single-skins of ten Melanophryniscus rubriventris toads (five collections of two toads each) captured during their breeding season in NW Argentina has revealed a total of 127 alkaloids of which 56 had not been previously detected in any frog or toad. Included among these new alkaloids are 23 new diastereomers of previously reported alkaloids. What is particularly distinguishing about the alkaloid profiles of these ten collections is the occurrence of many of the alkaloids, whether known or new to us, in only one of the ten skins sampled, despite two skins being obtained from each breeding site of the five populations. Many of the alkaloids are of classes known to have structures with branched-chains (e.g. pumiliotoxins and tricyclic structures) that are considered to derive from dietary mites. A large number of previously reported and new alkaloids are also of unclassified structures. Only a very few 3,5-disubstituted-indolizidine or -pyrrolizidine alkaloids are observed that have a straight-chain carbon skeleton and are likely derived from ant prey. The possible relationship of these collections made during the toad's brief breeding episodes to sequestration of dietary arthropods and individual alkaloid profiles is discussed.

  9. Alkaloids from single skins of the Argentinian toad Melanophryniscus rubriventris (ANURA, BUFONIDAE): An unexpected variability in alkaloid profiles and a profusion of new structures

    OpenAIRE

    Garraffo, H Martin; Andriamaharavo, Nirina R; Vaira, Marcos; Quiroga, Mar?a F; Heit, Cecilia; Spande, Thomas F

    2012-01-01

    GC-MS analysis of single-skins of ten Melanophryniscus rubriventris toads (five collections of two toads each) captured during their breeding season in NW Argentina has revealed a total of 127 alkaloids of which 56 had not been previously detected in any frog or toad. Included among these new alkaloids are 23 new diastereomers of previously reported alkaloids. What is particularly distinguishing about the alkaloid profiles of these ten collections is the occurrence of many of the alkaloids, w...

  10. Comparison of a specific HPLC determination of toxic aconite alkaloids in processed Radix aconiti with a titration method of total alkaloids.

    Science.gov (United States)

    Csupor, Dezso; Borcsa, Botond; Heydel, Barbara; Hohmann, Judit; Zupkó, István; Ma, Yan; Widowitz, Ute; Bauer, Rudolf

    2011-10-01

    In traditional Chinese medicine, Aconitum (Ranunculaceae) roots are only applied after processing. Nevertheless, several cases of poisoning by improperly processed aconite roots have been reported. The aim of this study was to develop a reliable analytical method to assess the amount of toxic aconite alkaloids in commercial aconite roots, and to compare this method with the commonly used total alkaloid content determination by titration. The content of mesaconitine, aconitine, and hypaconitine in 16 commercial samples of processed aconite roots was determined by an HPLC method and the total alkaloid content by indirect titration. Five samples were selected for in vivo toxicological investigation. In most of the commercial samples, toxic alkaloids were not detectable, or only traces were found. In four samples, we could detect >0.04% toxic aconite alkaloids, the highest with a content of 0.16%. The results of HPLC analysis were compared with the results obtained by titration, and no correlation was found between the two methods. The in vivo results reassured the validity of the HPLC determination. Samples with mesaconitine, aconitine, and hypaconitine content below the HPLC detection limit still contained up to 0.2% alkaloids determined by titration. Since titration of alkaloids gives no information selectively on the aconitine-type alkaloid content and toxicity of aconite roots this method is not appropriate for safety assessment. The HPLC method developed by us provides a quick and reliable assessment of toxicity and should be considered as a purity test in pharmacopoeia monographs.

  11. Tropane alkaloids in food: poisoning incidents

    NARCIS (Netherlands)

    Adamse, P.; Egmond, van H.P.; Noordam, M.Y.; Mulder, P.P.J.; Nijs, de W.C.M.

    2014-01-01

    A large number of wild and cultured plants produce secondary metabolites that can be toxic to humans and animals. The present study aims to provide insight into the routes of (un)intentional poisonings of humans by tropane alkaloids. Poisonings of humans by tropane alkaloids occur as unintended

  12. Pyrrolizidine alkaloids of Senecio sp from Peru

    International Nuclear Information System (INIS)

    Ruiz Vasquez, Liliana; Reina Artiles, Matias; Gonzalez Coloma, Azucena; Cabrera Perez, Raimundo; Ruiz Mesia, Lastenia

    2011-01-01

    Six pyrrolizidine alkaloids (PAs) (two saturated macrocyclic, three unsaturated macrocyclic and one unsaturated seco-macrocyclic) were isolated from native Peruvian Senecio species. The structures of these alkaloids were established by a complete NMR spectroscopic analysis, chemical transformations and comparison of their NMR data with those published for similar alkaloids. Three PAs were then tested for antifungal activity against Fusarium moniliforme, F. (Sheldon), F. oxysporum fs. lycopersici (Scheldt) and F. solani (Mart), no significant activity being observed. (author)

  13. Pyrrolizidine alkaloids of Senecio sp from Peru

    Energy Technology Data Exchange (ETDEWEB)

    Ruiz Vasquez, Liliana; Reina Artiles, Matias [Instituto de Productos Naturales y Agrobiologia, CSIC, Tenerife (Spain); Gonzalez Coloma, Azucena [Instituto de Ciencias Agrarias (ICA), CSIC, Madrid (Spain); Cabrera Perez, Raimundo [Universidad de La Laguna (ULL), Tenerife (Spain). Unidad de Fitopatologia, Facultad de Biologia; Ruiz Mesia, Lastenia [Universidad Nacional de la Amazonia Peruana (LIPNAA-UNAP), AA.HH. Nuevo San Lorenzo, San Juan, Iquitos (Peru). Lab. de Investigacion en Productos Naturales Antiparasitarios de la Amazonia

    2011-07-01

    Six pyrrolizidine alkaloids (PAs) (two saturated macrocyclic, three unsaturated macrocyclic and one unsaturated seco-macrocyclic) were isolated from native Peruvian Senecio species. The structures of these alkaloids were established by a complete NMR spectroscopic analysis, chemical transformations and comparison of their NMR data with those published for similar alkaloids. Three PAs were then tested for antifungal activity against Fusarium moniliforme, F. (Sheldon), F. oxysporum fs. lycopersici (Scheldt) and F. solani (Mart), no significant activity being observed. (author)

  14. Pyrrolizidine alkaloids of senecio sp from Peru

    Directory of Open Access Journals (Sweden)

    Liliana Ruiz Vásquez and Matías Reina Artiles

    2011-01-01

    Full Text Available Six pyrrolizidine alkaloids (PAs (two saturated macrocyclic, three unsaturated macrocyclic and one unsaturated seco-macrocyclic were isolated from native Peruvian Senecio species. The structures of these alkaloids were established by a complete NMR spectroscopic analysis, chemical transformations and comparison of their NMR data with those published for similar alkaloids. Three PAs were then tested for antifungal activity against Fusarium moniliforme, F. (Sheldon, F. oxysporum fs. lycopersici (Scheldt and F. solani (Mart, no significant activity being observed.

  15. Extrarenal potassium adaptation: role of skeletal muscle

    International Nuclear Information System (INIS)

    Blachley, J.D.; Crider, B.P.; Johnson, J.H.

    1986-01-01

    Following the ingestion of a high-potassium-content diet for only a few days, the plasma potassium of rats rises only modestly in response to a previously lethal dose of potassium salts. This acquired tolerance, termed potassium adaptation, is principally the result of increased capacity to excrete potassium into the urine. However, a substantial portion of the acute potassium dose is not immediately excreted and is apparently translocated into cells. Previous studies have failed to show an increase in the content of potassium of a variety of tissues from such animals. Using 86 Rb as a potassium analogue, we have shown that the skeletal muscle of potassium-adapted rats takes up significantly greater amounts of potassium in vivo in response to an acute challenge than does that of control animals. Furthermore, the same animals exhibit greater efflux of 86 Rb following the termination of the acute infusion. We have also shown that the Na+-K+-ATPase activity and ouabain-binding capacity of skeletal muscle microsomes are increased by the process of potassium adaptation. We conclude that skeletal muscle is an important participant in potassium adaptation and acts to temporarily buffer acute increases in the extracellular concentration of potassium

  16. Aporphine alkaloids from Ocotea macrophylla (Lauraceae)

    International Nuclear Information System (INIS)

    Pabon, Ludy Cristina; Cuca, Luis Enrique

    2010-01-01

    Four aporphine alkaloids from the wood of Ocotea macrophylla (Lauraceae) were isolated and characterized as (S)-3-methoxy-nordomesticine (1), (S)-N-ethoxycarbonyl-3-methoxy-nordomesticine (2), (S)-N-formyl-3-methoxy-nordomesticine (3) and (S)-N-methoxycarbonyl-3-methoxy-nordomesticine (4); alkaloids 2-4 are being report for the first time. The structure the isolated compounds were determined based on their spectral data and by comparison of their spectral data with values described in literature. The alkaloid fraction and compound 1 showed antifungal activity against Fusarium oxysporum f. sp. lycopersici and also compound 1 showed antimicrobial activity towards Staphylococcus aureus, Enterococcus faecalis as well. (author)

  17. Aporphine alkaloids from Ocotea macrophylla (Lauraceae)

    Energy Technology Data Exchange (ETDEWEB)

    Pabon, Ludy Cristina; Cuca, Luis Enrique, E-mail: lcpabonb@unal.edu.c [Universidad Nacional de Bogota (Colombia). Facultad de Ciencias. Dept. de Quimica

    2010-07-01

    Four aporphine alkaloids from the wood of Ocotea macrophylla (Lauraceae) were isolated and characterized as (S)-3-methoxy-nordomesticine (1), (S)-N-ethoxycarbonyl-3-methoxy-nordomesticine (2), (S)-N-formyl-3-methoxy-nordomesticine (3) and (S)-N-methoxycarbonyl-3-methoxy-nordomesticine (4); alkaloids 2-4 are being report for the first time. The structure the isolated compounds were determined based on their spectral data and by comparison of their spectral data with values described in literature. The alkaloid fraction and compound 1 showed antifungal activity against Fusarium oxysporum f. sp. lycopersici and also compound 1 showed antimicrobial activity towards Staphylococcus aureus, Enterococcus faecalis as well. (author)

  18. Aporphine alkaloids from Ocotea macrophylla (Lauraceae

    Directory of Open Access Journals (Sweden)

    Ludy Cristina Pabon

    2010-01-01

    Full Text Available Four aporphine alkaloids from the wood of Ocotea macrophylla (Lauraceae were isolated and characterized as (S-3-methoxy-nordomesticine (1, (S-N-ethoxycarbonyl-3-methoxy-nordomesticine (2, (S-N-formyl-3-methoxy-nordomesticine (3 and (S-N-methoxycarbonyl-3-methoxy-nordomesticine (4; alkaloids 2-4 are being report for the first time. The structure the isolated compounds were determined based on their spectral data and by comparison of their spectral data with values described in literature. The alkaloid fraction and compound 1 showed antifungal activity against Fusarium oxysporum f. sp. lycopersici and also compound 1 showed antimicrobial activity towards Staphylococcus aureus, Enterococcus faecalis as well.

  19. Single sodium channels from human skeletal muscle in planar lipid bilayers: characterization and response to pentobarbital

    NARCIS (Netherlands)

    Wartenberg, Hans C.; Urban, Bernd W.

    2004-01-01

    PURPOSE: To investigate the response to general anesthetics of different sodium-channel subtypes, we examined the effects of pentobarbital, a close thiopental analogue, on single sodium channels from human skeletal muscle and compared them to existing data from human brain and human ventricular

  20. Estimation of total alkaloid in Chitrakadivati by UV-Spectrophotometer.

    Science.gov (United States)

    Ajanal, Manjunath; Gundkalle, Mahadev B; Nayak, Shradda U

    2012-04-01

    Herbal formulation standardization by adopting newer technique is need of the hour in the field of Ayurvedic pharmaceutical industry. As very few reports exist. These kind of studies would certainly widen the herbal research area. Chitrakadivati is one such popular herbal formulation used in Ayurveda. Many of its ingredients are known for presence of alkaloids. Presence of alkaloid was tested qualitatively by Dragondroff's method then subjected to quantitative estimation by UV-Spectrophotometer. This method is based on the reaction between alkaloid and bromocresol green (BCG). Study discloses that out of 16 ingredients, 9 contain alkaloid. Chitrakadivati has shown 0.16% of concentration of alkaloid and which is significantly higher than it's individual ingredients.

  1. Genetics, Genomics and Evolution of Ergot Alkaloid Diversity

    Directory of Open Access Journals (Sweden)

    Carolyn A. Young

    2015-04-01

    Full Text Available The ergot alkaloid biosynthesis system has become an excellent model to study evolutionary diversification of specialized (secondary metabolites. This is a very diverse class of alkaloids with various neurotropic activities, produced by fungi in several orders of the phylum Ascomycota, including plant pathogens and protective plant symbionts in the family Clavicipitaceae. Results of comparative genomics and phylogenomic analyses reveal multiple examples of three evolutionary processes that have generated ergot-alkaloid diversity: gene gains, gene losses, and gene sequence changes that have led to altered substrates or product specificities of the enzymes that they encode (neofunctionalization. The chromosome ends appear to be particularly effective engines for gene gains, losses and rearrangements, but not necessarily for neofunctionalization. Changes in gene expression could lead to accumulation of various pathway intermediates and affect levels of different ergot alkaloids. Genetic alterations associated with interspecific hybrids of Epichloë species suggest that such variation is also selectively favored. The huge structural diversity of ergot alkaloids probably represents adaptations to a wide variety of ecological situations by affecting the biological spectra and mechanisms of defense against herbivores, as evidenced by the diverse pharmacological effects of ergot alkaloids used in medicine.

  2. Pyrrolizidine alkaloids from Heliotropium indicum

    International Nuclear Information System (INIS)

    Souza, Joao Sammy N.; Machado, Luciana L.; Pessoa, Otilia D.L.; Lemos, Telma L.G.; Braz-Filho, Raimundo; Overk, Cassia R.; Ping Yao; Cordell, Geoffrey A.

    2005-01-01

    Helindicine (1), a new pyrrolizidine alkaloid with unusual structural features, together with the known lycopsamine (2), were isolated from the roots of Heliotropium indicum (Boraginaceae). The structures were established by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and NOESY) and HREIMS. This is the first report of a lactone pyrrolizidine alkaloid in the genus Heliotropium. Compounds 1 and 2 were assayed for antioxidant activity and showed moderate activity. (author)

  3. Pyrrolizidine alkaloids from Heliotropium indicum

    Energy Technology Data Exchange (ETDEWEB)

    Souza, Joao Sammy N.; Machado, Luciana L.; Pessoa, Otilia D.L.; Lemos, Telma L.G. [Ceara Univ., Fortaleza, CE (Brazil). Dept. de Quimica Organica e Inorganica]. E-mail: tlemos@dqoi.ufc.br; Braz-Filho, Raimundo [Universidade Estadual do Norte Fluminense (UENF), Campos dos Goytacases, RJ (Brazil). Setor de Quimica de Produtos Naturais; Overk, Cassia R.; Ping Yao; Cordell, Geoffrey A. [University of Illinois at Chicago, IL (United States). College of Pharmacy. Dept. of Medicinal Chemistry and Pharmacognosy

    2005-11-15

    ndicine (1), a new pyrrolizidine alkaloid with unusual structural features, together with the known lycopsamine (2), were isolated from the roots of Heliotropium indicum (Boraginaceae). The structures were established by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and NOESY) and HREIMS. This is the first report of a lactone pyrrolizidine alkaloid in the genus Heliotropium. Compounds 1 and 2 were assayed for antioxidant activity and showed moderate activity. (author)

  4. New pyrrolizidine alkaloids from Heliotropium crassifolium.

    Science.gov (United States)

    Farsam, H; Yassa, N; Sarkhail, P; Shafiee, A

    2000-05-01

    Heliotropium crassifolium Boiss, (Boraginaceae) from a population of Ilam, western region of Iran was studied for pyrrolizidine alklaoids (PAs). Four alkaloids have been identified: europine 1, europine N-oxide 2 and a new pyrrolizidine alkaloids ilamine 3 and its N-oxide 4, respectively. Their structures were elucidated by IR, 1H-NMR and EIMS data.

  5. Bioactive alkaloids produced by fungi. I. Updates on alkaloids from the species of the genera Boletus, Fusarium and psilocybe.

    Science.gov (United States)

    Mahmood, Zafar Alam; Ahmed, Syed Waseemuddin; Azhar, Iqbal; Sualeh, Mohammad; Baig, Mirza Tasawer; Zoha, Sms

    2010-07-01

    Fungi, in particular, are able in common with the higher plants and bacteria, to produce metabolites, including alkaloids. Alkaloids, along with other metabolites are the most important fungal metabolites from pharmaceutical and industrial point of view. Based on this observation, the authors of this review article have tried to provide an information on the alkaloids produced by the species of genera: Boletus, Fusarium and Psilocybef from 1981-2009. Thus the review would be helpful and provides valuable information for the researchers of the same field.

  6. Studies of interaction between two alkaloids and double helix DNA

    International Nuclear Information System (INIS)

    Sun, Yantao; Peng, Tingting; Zhao, Lei; Jiang, Dayu; Cui, Yuncheng

    2014-01-01

    This article presents the study on the interaction of two alkaloids (matrine and evodiamine) and hs-DNA by absorption, fluorescence, circular dichroism (CD), DNA melting and viscosity experiments. The spectroscopic studies suggested that two alkaloids can bind to DNA through an intercalative mode. The viscosity measurement and thermal denaturation also indicated that two alkaloids can intercalate to DNA. The binding constants (K A ) and the number of binding sites (n) were determined. At the same time, some significant thermodynamic parameters of the binding of the alkaloids to DNA were obtained. Competitive binding studies revealed that alkaloids had an effect on ethidium bromide (EB) bound DNA. In addition, it was also proved that the fluorescence quenching was influenced by ionic strength. - Highlights: • Interaction between two alkaloids and DNA is studied by spectral methods. • The binding constant and the binding sites between two alkaloids and DNA are obtained. • There are a classical intercalative mode between alkaloids and DNA. • The binding of matrine with DNA is weaker than that of evodiamine. • It is important for us to understand the alkaloids–DNA interactions at a molecular level

  7. Pyrrolizidine alkaloids from Heliotropium indicum

    OpenAIRE

    Souza,João Sammy N.; Machado,Luciana L.; Pessoa,Otília D. L.; Braz-Filho,Raimundo; Overk,Cassia R.; Yao,Ping; Cordell,Geoffrey A.; Lemos,Telma L. G.

    2005-01-01

    Helindicine (1), a new pyrrolizidine alkaloid with unusual structural features, together with the known lycopsamine (2), were isolated from the roots of Heliotropium indicum (Boraginaceae). The structures were established by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and NOESY) and HREIMS. This is the first report of a lactone pyrrolizidine alkaloid in the genus Heliotropium. Compounds 1 and 2 were assayed for antioxidant activity and showed moderate activity. Um novo alcaló...

  8. Racemic alkaloids from the fungus Ganoderma cochlear.

    Science.gov (United States)

    Wang, Xin-Long; Dou, Man; Luo, Qi; Cheng, Li-Zhi; Yan, Yong-Ming; Li, Rong-Tao; Cheng, Yong-Xian

    2017-01-01

    Seven pairs of new alkaloid enantiomers, ganocochlearines C-I (1, 3-8), and three pairs of known alkaloids were isolated from the fruiting bodies of Ganoderma cochlear. The chemical structures of new compounds were elucidated on the basis of 1D and 2D NMR data. The absolute configurations of compounds 1, 3-10 were assigned by ECD calculations. Biological activities of these isolates against renal fibrosis were accessed in rat normal or diseased renal interstitial fibroblast cells. Importantly, the plausible biosynthetic pathway for this class of alkaloids was originally proposed. Copyright © 2016 Elsevier B.V. All rights reserved.

  9. Hemlock alkaloids from Socrates to poison aloes.

    Science.gov (United States)

    Reynolds, Tom

    2005-06-01

    Hemlock (Conium maculatum L. Umbelliferae) has long been known as a poisonous plant. Toxicity is due to a group of piperidine alkaloids of which the representative members are coniine and gamma-coniceine. The latter is the more toxic and is the first formed biosynthetically. Its levels in relation to coniine vary widely according to environmental conditions and to provenance of the plants. Surprisingly, these piperidine alkaloids have turned up in quite unrelated species in the monocotyledons as well as the dicotyledons. Aloes, for instance, important medicinal plants, are not regarded as poisonous although some species are very bitter. Nevertheless a small number of mostly local species contain the alkaloids, especially gamma-coniceine and there have been records of human poisoning. The compounds are recognized by their characteristic mousy smell. Both acute and chronic symptoms have been described. The compounds are neurotoxins and death results from respiratory failure, recalling the effects of curare. Chronic non-lethal ingestion by pregnant livestock leads to foetal malformation. Both acute and chronic toxicity are seen with stock in damp meadows and have been recorded as problems especially in North America. The alkaloids derive biosynthetically from acetate units via the polyketide pathway in contrast to other piperidine alkaloids which derive from lysine.

  10. A bio-inspired apposition compound eye machine vision sensor system

    International Nuclear Information System (INIS)

    Davis, J D; Barrett, S F; Wright, C H G; Wilcox, M

    2009-01-01

    The Wyoming Information, Signal Processing, and Robotics Laboratory is developing a wide variety of bio-inspired vision sensors. We are interested in exploring the vision system of various insects and adapting some of their features toward the development of specialized vision sensors. We do not attempt to supplant traditional digital imaging techniques but rather develop sensor systems tailor made for the application at hand. We envision that many applications may require a hybrid approach using conventional digital imaging techniques enhanced with bio-inspired analogue sensors. In this specific project, we investigated the apposition compound eye and its characteristics commonly found in diurnal insects and certain species of arthropods. We developed and characterized an array of apposition compound eye-type sensors and tested them on an autonomous robotic vehicle. The robot exhibits the ability to follow a pre-defined target and avoid specified obstacles using a simple control algorithm.

  11. Alkaloids in the human food chain--natural occurrence and possible adverse effects.

    Science.gov (United States)

    Koleva, Irina I; van Beek, Teris A; Soffers, Ans E M F; Dusemund, Birgit; Rietjens, Ivonne M C M

    2012-01-01

    Alkaloid-containing plants are an intrinsic part of the regular Western diet. The present paper summarizes the occurrence of alkaloids in the food chain, their mode of action and possible adverse effects including a safety assessment. Pyrrolizidine alkaloids are a reason for concern because of their bioactivation to reactive alkylating intermediates. Several quinolizidine alkaloids, β-carboline alkaloids, ergot alkaloids and steroid alkaloids are active without bioactivation and mostly act as neurotoxins. Regulatory agencies are aware of the risks and have taken or are considering appropriate regulatory actions for most alkaloids. These vary from setting limits for the presence of a compound in feed, foods and beverages, trying to define safe upper limits, advising on a strategy aiming at restrictions in use, informing the public to be cautious or taking specific plant varieties from the market. For some alkaloids known to be present in the modern food chain, e.g., piperine, nicotine, theobromine, theophylline and tropane alkaloids risks coming from the human food chain are considered to be low if not negligible. Remarkably, for many alkaloids that are known constituents of the modern food chain and of possible concern, tolerable daily intake values have so far not been defined. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  12. Cytotoxicity and accumulation of ergot alkaloids in human primary cells.

    Science.gov (United States)

    Mulac, Dennis; Humpf, Hans-Ulrich

    2011-04-11

    Ergot alkaloids are secondary metabolites produced by fungi of the species Claviceps. Toxic effects after consumption of contaminated grains are described since mediaeval times. Of the more than 40 known ergot alkaloids six are found predominantly. These are ergotamine, ergocornine, ergocryptine, ergocristine, ergosine and ergometrine, along with their corresponding isomeric forms (-inine-forms). Toxic effects are known to be induced by an interaction of the ergot alkaloids as neurotransmitters, like dopamine or serotonin. Nevertheless data concerning cytotoxic effects are missing and therefore a screening of the six main ergot alkaloids was performed in human primary cells in order to evaluate the toxic potential. As it is well known that ergot alkaloids isomerize easily the stability was tested in the cell medium. Based on these results factors were calculated to correct the used concentration values to the biologically active lysergic (-ine) form. These factors range from 1.4 for the most stable compound ergometrine to 5.0 for the most unstable ergot alkaloid ergocristine. With these factors, reflecting the instability, several controverse literature data concerning the toxicity could be explained. To evaluate the cytotoxic effects of ergot alkaloids, human cells in primary culture were used. These cells remain unchanged in contrast to cell lines and the data allow a better comparison to the in vivo situation than using immortalized cell lines. To characterize the effects on primary cells, renal proximal tubule epithelial cells (RPTEC) and normal human astrocytes (NHA) were used. The parameters necrosis (LDH-release) and apoptosis (caspase-3-activation, DNA condensation and fragmentation) were distinguished. The results show that depending on the individual structure of the peptide ergot alkaloids the toxic properties change. While ergometrine as a lysergic acid amide did not show any effect, the peptide ergot alkaloids revealed a different toxic potential. Of

  13. Genetic variation of piperidine alkaloids in Pinus ponderosa: a common garden study.

    Science.gov (United States)

    Gerson, Elizabeth A; Kelsey, Rick G; St Clair, J Bradley

    2009-02-01

    Previous measurements of conifer alkaloids have revealed significant variation attributable to many sources, environmental and genetic. The present study takes a complementary and intensive, common garden approach to examine genetic variation in Pinus ponderosa var. ponderosa alkaloid production. Additionally, this study investigates the potential trade-off between seedling growth and alkaloid production, and associations between topographic/climatic variables and alkaloid production. Piperidine alkaloids were quantified in foliage of 501 nursery seedlings grown from seed sources in west-central Washington, Oregon and California, roughly covering the western half of the native range of ponderosa pine. A nested mixed model was used to test differences among broad-scale regions and among families within regions. Alkaloid concentrations were regressed on seedling growth measurements to test metabolite allocation theory. Likewise, climate characteristics at the seed sources were also considered as explanatory variables. Quantitative variation from seedling to seedling was high, and regional variation exceeded variation among families. Regions along the western margin of the species range exhibited the highest alkaloid concentrations, while those further east had relatively low alkaloid levels. Qualitative variation in alkaloid profiles was low. All measures of seedling growth related negatively to alkaloid concentrations on a natural log scale; however, coefficients of determination were low. At best, annual height increment explained 19.4 % of the variation in ln(total alkaloids). Among the climate variables, temperature range showed a negative, linear association that explained 41.8 % of the variation. Given the wide geographic scope of the seed sources and the uniformity of resources in the seedlings' environment, observed differences in alkaloid concentrations are evidence for genetic regulation of alkaloid secondary metabolism in ponderosa pine. The theoretical

  14. Toxicosis by Plant Alkaloids in Humans and Animals in Colombia

    Directory of Open Access Journals (Sweden)

    Gonzalo J. Diaz

    2015-12-01

    Full Text Available Due to its tropical location, chains of mountains, inter-Andean valleys, Amazon basin area, eastern plains and shores on both the Atlantic and Pacific Oceans, Colombia has many ecosystems and the second largest plant biodiversity in the world. Many plant species, both native and naturalized, are currently recognized as toxic for both animals and humans, and some of them are known to cause their toxic effects due to their alkaloid content. Among these, there are plants containing the hepatotoxic pyrrolizidine alkaloids, neurotoxins such as the indolizidine alkaloid swainsonine and the piperidine alkaloids coniine and γ-coniceine and tropane alkaloids. Unfortunately, the research in toxic plants in Colombia is not nearly proportional to its plant biodiversity and the scientific information available is only very scarce. The present review aims at summarizing the scarce information about plant alkaloid toxicosis in animals and humans in Colombia.

  15. Toxicosis by Plant Alkaloids in Humans and Animals in Colombia

    Science.gov (United States)

    Diaz, Gonzalo J.

    2015-01-01

    Due to its tropical location, chains of mountains, inter-Andean valleys, Amazon basin area, eastern plains and shores on both the Atlantic and Pacific Oceans, Colombia has many ecosystems and the second largest plant biodiversity in the world. Many plant species, both native and naturalized, are currently recognized as toxic for both animals and humans, and some of them are known to cause their toxic effects due to their alkaloid content. Among these, there are plants containing the hepatotoxic pyrrolizidine alkaloids, neurotoxins such as the indolizidine alkaloid swainsonine and the piperidine alkaloids coniine and γ-coniceine and tropane alkaloids. Unfortunately, the research in toxic plants in Colombia is not nearly proportional to its plant biodiversity and the scientific information available is only very scarce. The present review aims at summarizing the scarce information about plant alkaloid toxicosis in animals and humans in Colombia. PMID:26690479

  16. Norepinephrine alkaloids as antiplasmodial agents: Synthesis of syncarpamide and insight into the structure-activity relationships of its analogues as antiplasmodial agents.

    Science.gov (United States)

    Aratikatla, Eswar K; Valkute, Tushar R; Puri, Sunil K; Srivastava, Kumkum; Bhattacharya, Asish K

    2017-09-29

    Syncarpamide 1, a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC 50 values of 2.04 μM (D6 clone), 3.06 μM (W2 clone) and observed by us 3.90 μM (3D7 clone) and 2.56 μM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, (R)-2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds (3-57), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer (S)-58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, (S)-41 and its enantiomer, (R)-42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC 50 values of 3.16, 2.28 μM (3D7) and 1.78, 2.07 μM (K1), respectively than the natural product, syncarpamide 1. Three compounds (S)-13, (S)-17, (S)-21 exhibited antiplasmodial activities with IC 50 values of 6.39, 6.82, 6.41 μM against 3D7 strain, 4.27, 7.26, 2.71 μM against K1 strain and with CC 50 values of 147.72, 153.0, >200 μM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1

  17. Analysis, separation, and bioassay of pyrrolizidine alkaloids from comfrey (Symphytum officinale).

    Science.gov (United States)

    Couet, C E; Crews, C; Hanley, A B

    1996-01-01

    Pyrrolizidine alkaloids have been linked to liver and lung cancers and a range of other deleterious effects. As with many natural toxicants, major problems arise in determining the effects of the different members of the class and the importance of various forms of ingestion. In this study we have investigated the levels of pyrrolizidine alkaloids in comfrey (Symphytum officinale), determined the levels in different parts of the plant and in herbal remedies, separated the alkaloids into two main groups--the principal parent alkaloids and the corresponding N-oxides--and, finally, carried out a simple bioassay based upon the mutagenic capability of the separated compounds in a human cell line. We conclude that the part of the plant ingested is important in terms of alkaloid challenge and that the effect of two of the major groups of alkaloids individually is different from that of alkaloids in the whole plant extract.

  18. Initial Studies on Alkaloids from Lombok Medicinal Plants

    Directory of Open Access Journals (Sweden)

    John B. Bremner

    2001-01-01

    Full Text Available Initial investigation of medicinal plants from Lombok has resulted in the collection of 100 plant species predicted to have antimicrobial, including antimalarial, properties according to local medicinal uses. These plants represent 49 families and 80 genera; 23% of the plants tested positively for alkaloids. Among the plants testing positive, five have been selected for further investigation involving structure elucidation and antimicrobial testing on the extracted alkaloids. Initial work on structural elucidation of some of the alkaloids is reported briefly.

  19. Effect of processing on the alkaloids in Aconitum tubers by HPLC-TOF/MS

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    Min Liu

    2017-06-01

    Full Text Available According to the Chinese Pharmacopoeia 2015, only processed Aconitum tubers can be clinically applied, and the effect of processing is unclear. This research aimed to explore the effect of processing on cardiac efficacy of alkaloids in Aconitum tubers. First, the chemical ingredients in unprocessed and processed Aconitum tubers were identified and compared by using high performance liquid chromatography time-of-flight mass spectrometry (HPLC-TOF/MS and multivariate pattern recognition methods. Then the representative alkaloids in Aconitum tubers, aconitine, benzoylaconine, and aconine, which belong to diester-diterpenoid alkaloids, monoester-diterpenoid alkaloids, and amine-diterpenoid alkaloids, respectively, were selected for further validation of attenuated mechanism. Subsequent pharmacological experiments with aconitine, benzoylaconine, and aconine in SD rats were used for validate the effect of processing on cardiac functions. After processing the Aconitum tubers, it was found that the contents of diester-diterpenoid alkaloids were reduced, and those of monoester-diterpenoid alkaloids and amine-diterpenoid alkaloids were increased, suggesting that diester-diterpenoid alkaloids were transformed into monoester-diterpenoid alkaloids and amine-diterpenoid alkaloids. Through further decocting the aconitine in boiling water, it was confirmed that the three alkaloids could be progressively transformed. Pharmacological experiments with aconitine, benzoylaconine, and aconine in SD rats showed that aconitine at a dose of 0.01 mg/kg and aconine at a dose of 10 mg/kg enhanced the cardiac function, while benzoylaconine at a dose of 2 mg/kg weakened the cardiac function. The effect of processing is attributed to the transformation of the most toxic diester-diterpenoid alkaloids into less toxic monoester-diterpenoid alkaloids and amine-diterpenoid alkaloids.

  20. New extraction technique for alkaloids

    Directory of Open Access Journals (Sweden)

    Djilani Abdelouaheb

    2006-01-01

    Full Text Available A method of extraction of natural products has been developed. Compared with existing methods, the new technique is rapid, more efficient and consumes less solvent. Extraction of alkaloids from natural products such as Hyoscyamus muticus, Datura stramonium and Ruta graveolens consists of the use of a sonicated solution containing a surfactant as extracting agent. The alkaloids are precipitated by Mayer reagent, dissolved in an alkaline solution, and then extracted with chloroform. This article compares the results obtained with other methods showing clearly the advantages of the new method.

  1. Two New Acridone Alkaloids from Glycosmis macrantha

    Directory of Open Access Journals (Sweden)

    Abdah Md Akim

    2011-05-01

    Full Text Available Extraction and chromatographic separation of the extracts of dried stem barks of Glycosmis macrantha lead to isolation of two new acridone alkaloids, macranthanine (1 and 7-hydroxynoracronycine (2, and a known acridone, atalaphyllidine (3. The structures of these alkaloids were determined by detailed spectral analysis and also by comparison with reported data.

  2. A strategy for complex dimer formation when biomimicry fails: total synthesis of ten coccinellid alkaloids.

    Science.gov (United States)

    Sherwood, Trevor C; Trotta, Adam H; Snyder, Scott A

    2014-07-09

    Although dimeric natural products can often be synthesized in the laboratory by directly merging advanced monomers, these approaches sometimes fail, leading instead to non-natural architectures via incorrect unions. Such a situation arose during our studies of the coccinellid alkaloids, when attempts to directly dimerize Nature's presumed monomeric precursors in a putative biomimetic sequence afforded only a non-natural analogue through improper regiocontrol. Herein, we outline a unique strategy for dimer formation that obviates these difficulties, one which rapidly constructs the coccinellid dimers psylloborine A and isopsylloborine A through a terminating sequence of two reaction cascades that generate five bonds, five rings, and four stereocenters. In addition, a common synthetic intermediate is identified which allows for the rapid, asymmetric formal or complete total syntheses of eight monomeric members of the class.

  3. Steroidal glyco alkaloids and molluscicidal activity of Solanum asperum Rich. fruits

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Tania M.S. [Instituto Multidisciplinar em Saude, Vitoria da Conquista, BA (Brazil). Campus Avancado Anisio Teixeira]. E-mail: sarmento@pesquisador.cnpq.br; Camara, Celso A. [Universidade Federal Rural de Pernambuco, Recife, PE (Brazil). Dept. de Quimica; Freire, Kristerson R.L.; Silva, Thiago G. da; Agra, Maria de F.; Bhattacharyya, Jnanabrata [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil). Lab. de Tecnologia Farmaceutica

    2008-07-01

    Bioassay-guided fractionation of the alkaloidal extract of the green fruits of Solanum asperum afforded a new compound, solanandaine along with solasonine and solamargine. The total crude alkaloids as well as the isolated pure alkaloids exhibited significant molluscicidal activity. (author)

  4. New zwitterionic monoterpene indole alkaloids from Uncaria rhynchophylla.

    Science.gov (United States)

    Guo, Qiang; Yang, Hongshuai; Liu, Xinyu; Si, Xiali; Liang, Hong; Tu, Pengfei; Zhang, Qingying

    2018-01-31

    Four new zwitterionic monoterpene indole alkaloids, rhynchophyllioniums A-D (1-4), together with eight known alkaloids (5-12), were isolated from the hook-bearing stems of Uncaria rhynchophylla. Their structures were elucidated by extensive spectroscopic data analysis of MS, 1D and 2D NMR, and ECD, and the zwitterionic forms and absolute configurations of 1 and 2 were unambiguously confirmed by single crystal X-ray diffraction analysis. All the isolates, including the monoterpene indole alkaloids with free C-22 carboxyl group and those with C-22 carboxyl methyl ester, were proved to be naturally coexisting in the herb by LC-MS analysis. This is the first report of monoterpene indole alkaloids that exist in the form of zwitterion. Additionally, the cytotoxic activities of all isolates against A549, HepG2, and MCF-7 cell lines are reported. Copyright © 2018 Elsevier B.V. All rights reserved.

  5. Total alkaloid content in various fractions of Tabernaemonata sphaerocarpa Bl. (Jembirit) leaves

    Science.gov (United States)

    Salamah, N.; Ningsih, D. S.

    2017-11-01

    Tabernaemontana sphaerocarpa Bl. (Jembirit) is one of the Apocynaceae family plants containing alkaloid compound. Traditionally, it is used as an anti-inflammatory medicine. It is found to have a new bisindole alkaloid compound that shows a potent cytotoxic activity in human cancer. This study aimed to know the total alkaloid content in some fractions of ethanolic extract of T. sphaerocarpa Bl. leaf powder was extracted by maceration method in 70% ethanol solvent. Then, the extract was fractionated in a separatory funnel using water, ethyl acetate, and hexane. The total alkaloid content in each fraction was analyzed with visible spectrophotometric methods based on the reaction with Bromocresol Green (BCG). The total alkaloids in water fraction and ethyl acetate fraction were (0.0312±0.0009)% and (0.0281±0.0014)%, respectively. Meanwhile, the total alkaloid content in hexane was not detected. The statistical analysis, performed in SPSS, resulted in a significant difference between the total alkaloids in water fraction and ethyl acetate fraction. The total alkaloid in water fraction of T. sphaerocarpa Bl. was higher than the one in ethyl acetate fraction.

  6. Analogue Gravity

    Directory of Open Access Journals (Sweden)

    Carlos Barceló

    2011-05-01

    Full Text Available Analogue gravity is a research programme which investigates analogues of general relativistic gravitational fields within other physical systems, typically but not exclusively condensed matter systems, with the aim of gaining new insights into their corresponding problems. Analogue models of (and for gravity have a long and distinguished history dating back to the earliest years of general relativity. In this review article we will discuss the history, aims, results, and future prospects for the various analogue models. We start the discussion by presenting a particularly simple example of an analogue model, before exploring the rich history and complex tapestry of models discussed in the literature. The last decade in particular has seen a remarkable and sustained development of analogue gravity ideas, leading to some hundreds of published articles, a workshop, two books, and this review article. Future prospects for the analogue gravity programme also look promising, both on the experimental front (where technology is rapidly advancing and on the theoretical front (where variants of analogue models can be used as a springboard for radical attacks on the problem of quantum gravity.

  7. Alkaloids in bufonid toads (melanophryniscus): temporal and geographic determinants for two argentinian species.

    Science.gov (United States)

    Daly, J W; Wilham, J M; Spande, T F; Garraffo, H M; Gil, R R; Silva, G L; Vaira, M

    2007-04-01

    Bufonid toads of the genus Melanophryniscus represent one of several lineages of anurans with the ability to sequester alkaloids from dietary arthropods for chemical defense. The alkaloid profile for Melanophryniscus stelzneri from a location in the province of Córdoba, Argentina, changed significantly over a 10-year period, probably indicating changes in availability of alkaloid-containing arthropods. A total of 29 alkaloids were identified in two collections of this population. Eight alkaloids were identified in M. stelzneri from another location in the province of Córdoba. The alkaloid profiles of Melanophryniscus rubriventris collected from four locations in the provinces of Salta and Jujuy, Argentina, contained 44 compounds and differed considerably between locations. Furthermore, alkaloid profiles of M. stelzneri and M. rubriventris strongly differed, probably reflecting differences in the ecosystem and hence in availability of alkaloid-containing arthropods.

  8. Isolation, Identification, and Xanthine Oxidase Inhibition Activity of Alkaloid Compound from Peperomia pellucida

    Science.gov (United States)

    Fachriyah, E.; Ghifari, M. A.; Anam, K.

    2018-04-01

    The research of the isolation and xanthine oxidation inhibition activity of alkaloid compound from Peperomia pellucida has been carried out. Alkaloid extract is isolated by column chromatography and preparative TLC. Alkaloid isolate is identified spectroscopically by UV-Vis spectrophotometer, FT-IR, and LC-MS/MS. Xanthine oxidase inhibition activity is carried out by in vitro assay. The result showed that the alkaloid isolated probably has piperidine basic structure. The alkaloid isolate has N-H, C-H, C = C, C = O, C-N, C-O-C groups and the aromatic ring. The IC50 values of ethanol and alkaloid extract are 71.6658 ppm and 76.3318 ppm, respectively. Alkaloid extract of Peperomia pellucida showed higher activity than ethanol extract.

  9. NOVEL ALKALOID FROM Rauvolfia capixabae(APOCYNACEAE

    Directory of Open Access Journals (Sweden)

    Lanamar Almeida Carlos

    2016-02-01

    Full Text Available A new sarpagine-type alkaloid, Na-methylrauflorine (1, was isolated from Rauvolfia capixabaetogether with isoreserpiline (2,Nb-oxide-isoreserpiline (3, ajmalicine (4, perakine (5 and vinorine (6 alkaloids. These compounds were characterized based on their spectral data basis, mainly one- (1H, 13C, APT and two-dimensional(1H-1H-COSY, 1H-1H-NOESY, HMQC and HMBC NMR, and mass spectra, also involving comparison with data from the literature.

  10. Antimicrobial potential of alkaloids and flavonoids extracted from ...

    African Journals Online (AJOL)

    Background: Alkaloids and flavonoids are secondary metabolites extracted from different medicinal plants. Tamarix aphylla a traditionally valuable medicinal plant; was used for the extraction of alkaloids and flavonoids in order to evaluate their antibacterial activity. Methodology: The leaves of the plant were collected from ...

  11. Novel Euglenoid Derived Alkaloid

    Data.gov (United States)

    National Oceanic and Atmospheric Administration, Department of Commerce — Disclosed herein is a purified toxin isolated from Euglena sanguinea. More specifically the toxin, termed euglenophycin, is an alkaloid having herbicidal and...

  12. Two New Alkaloids from Narcissus serotinus L.

    Directory of Open Access Journals (Sweden)

    Francesc Viladomat

    2010-10-01

    Full Text Available The Amaryllidaceae family is well known for the presence of an exclusive group of alkaloids with a wide range of biological activities. Narcissus serotinus L. is a plant belonging to this family and its geographical distribution is mainly located along the Mediterranean coast. In the present work, specimens collected near Casablanca (Morocco were used to study the alkaloid content of this species. Starting with 350 g of the whole plant we used standard extraction and purification procedures to obtain fractions and compounds for GC-MS and NMR analysis. As well as five known alkaloids, we isolated two new compounds: 1-O-(3´-acetoxybutanoyllycorine and narseronine. The latter has been previously published, but with an erroneous structure.

  13. Alkaloid analysis by high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance

    DEFF Research Database (Denmark)

    Johansen, Kenneth; Ebild, S.J.; Christensen, S.B.

    2012-01-01

    %) as methanol-d containing 5% aqueous NHOH (30%) as eluents were successful, even though elution of alkaloids with pK of the corresponding acid above 10 proved difficult. Alkaloid extracts of Huperzia selago containing complex aliphatic alkaloids and Triclisia patens containing bisbenzylisoquinoline alkaloids...

  14. Effects of motherwort alkaloids on rat ear acne

    Directory of Open Access Journals (Sweden)

    Miao Mingsan

    2016-04-01

    Full Text Available The aim of this study was to explore the effects of motherwort alkaloids on rat ear acne. The rats that were administered high, medium, and low doses of motherwort alkaloids, tanshinone capsules, a model and a control group. Each group of rats was subjected to gavage once daily for 14 consecutive days. On the first day of testing, the control and model groups were administered an intradermal auricle injection of sterilized saline solution and the remaining groups were administered an intradermal auricle injection of Staphylococcus epidermidis in addition to the gavage. The thicknesses of the rats’ auricles were measured for five consecutive days following the injections. Anticoagulated blood was used for erythrocyte rheology index measurement. In addition, the entire ear of each rat was removed for morphological examination. Compared to the model group, the group administered motherwort alkaloids exhibited significantly reduced swelling, improved localized auricle proliferation, and reduced blood viscosity. This result suggests motherwort alkaloids are effective in rat ear acne.

  15. Isolation and structure elucidation of a new indole alkaloid from Rauvolfia serpentina hairy root culture: the first naturally occurring alkaloid of the raumacline group.

    Science.gov (United States)

    Sheludko, Yuri; Gerasimenko, Irina; Kolshorn, Heinz; Stöckigt, Joachim

    2002-05-01

    A new monoterpenoid indole alkaloid, 10-hydroxy- N(alpha)-demethyl-19,20-dehydroraumacline ( 1), was isolated as a mixture of E- and Z-isomers from hairy root culture of Rauvolfia serpentina Benth. ex Kurz (Apocynaceae) and the structure was determined by 1D and 2D NMR analyses. The new indole alkaloid represents the first naturally occurring alkaloid of the raumacline group and its putative biosynthetical pathway is discussed.

  16. [Effects of steaming and baking on content of alkaloids in Aconite Lateralis Radix (Fuzi)].

    Science.gov (United States)

    Yang, Chang-lin; Huang, Zhi-fang; Zhang, Yi-han; Liu, Yu-hong; Liu, Yun-huan; Chen, Yan; Yi, Jin-hai

    2014-12-01

    To study the effect of steaming and baking process on contents of alkaloids in Aconite Lateralis Radix (Fuzi), 13 alkaloids were analyzed by UPLC-MS/MS equipped with ESI ion source in MRM mode. In steaming process, the contents of diester-diterpenoid alkaloids decreased rapidly, the contents of monoester-diterpenoid alkaloids firstly increased, reached the peak at 40 min, and then deceased gradually. The contents of aconine alkaloids (mesaconine, aconine and hypaconine) increased all the time during processing, while the contents of fuziline, songorine, karacoline, salsolionl were stable or slightly decreased. In baking process, dynamic variations of alkaloids were different from that in the steaming process. Diester-diterpenoid alkaloids were degraded slightly slower than in steaming process. Monoester-diterpenoid alkaloids, aconine alkaloids and the total alkaloids had been destroyed at different degrees, their contents were significantly lower than the ones in steaming Fuzi at the same processing time. This experiment revealed the dynamic variations of alkaloids in the course of steaming and baking. Two processing methods which can both effectively remove the toxic ingredients and retain the active ingredients are simple and controllable, and are valuable for popularization and application.

  17. Biological armors under impact—effect of keratin coating, and synthetic bio-inspired analogues

    International Nuclear Information System (INIS)

    Achrai, B; Wagner, H D; Bar-On, B

    2015-01-01

    A number of biological armors, such as turtle shells, consist of a strong exoskeleton covered with a thin keratin coating. The mechanical role upon impact of this keratin coating has surprisingly not been investigated thus far. Low-velocity impact tests on the turtle shell reveal a unique toughening phenomenon attributed to the thin covering keratin layer, the presence of which noticeably improves the fracture energy and shell integrity. Synthetic substrate/coating analogues were subsequently prepared and exhibit an impact behavior similar to the biological ones. The results of the present study may improve our understanding, and even future designs, of impact-tolerant structures. (paper)

  18. Studies on the Alkaloids of the Calycanthaceae and Their Syntheses

    Directory of Open Access Journals (Sweden)

    Jin-Biao Xu

    2015-04-01

    Full Text Available Plants of the Calycanthaceae family, which possesses four genera and about 15 species, are mainly distributed in China, North America and Australia. Chemical studies on the Calycanthaceae have led to the discovery of about 14 alkaloids of different skeletons, including dimeric piperidinoquinoline, dimeric pyrrolidinoindoline and/or trimeric pyrrolidinoindolines, which exhibit significant anti-convulsant, anti-fungal, anti-viral analgesic, anti-tumor, and anti-melanogenesis activities. As some of complex tryptamine-derived alkaloids exhibit promising biological activities, the syntheses of these alkaloids have also been a topic of interest in synthetic chemistry during the last decades. This review will focus on the structures and total syntheses of these alkaloids.

  19. New derivatives of alkaloids peganine, vazicinone and garmine

    International Nuclear Information System (INIS)

    Agedilova, M.T.; Turmukhambetov, A.Zh.; Kazantsev, A.V.; Shul'ts, E.E.

    2005-01-01

    It was studied the chemical modification of chinazolin alkaloids peganine and vasicinone and indolin alkaloid garmine. The corresponding halogen-, alkyl-, cetyl and hydrazone derivatives and its salts were obtained. The structure of synthesized compounds was definite by following spectral methods: IR, UV, 1 H, 13 C and 11 B NMR spectroscopy

  20. Potential of solid state fermentation for production of ergot alkaloids

    OpenAIRE

    Trejo Hernandez, M.R.; Raimbault, Maurice; Roussos, Sevastianos; Lonsane, B.K.

    1992-01-01

    Production of total ergot alkaloids by #Claviceps fusiformis$ in solid state fermentation was 3.9 times higher compared to that in submerged fermentation. Production was equal in the case of #Claviceps purpurea$ but the spectra of alkaloids were advantageous with the use of solid state fermentation. The data establish potential of solid state fermentation which was not explored earlier for production of ergot alkaloids. (Résumé d'auteur)

  1. Detection and quantification of pyrrolizidine alkaloids in antibacterial medical honeys.

    Science.gov (United States)

    Cramer, Luise; Beuerle, Till

    2012-12-01

    In recent years, there has been an increasing interest in antibacterial honey for wound care ranging from minor abrasions and burns to leg ulcers and surgical wounds. On the other hand, several recent studies demonstrated that honey for human consumption was contaminated with natural occurring, plant derived pyrrolizidine alkaloids.1,2-Unsaturated pyrrolizidine alkaloids are a group of secondary plant metabolites that show developmental, hepato-, and geno-toxicity as well as carcinogenic effects in animal models and in in vitro test systems. Hence, it was of particular interest to analyze the pyrrolizidine alkaloid content of medical honeys intended for wound care.19 different medical honey samples and/or batches were analyzed by applying a recently established pyrrolizidine alkaloid sum parameter method. 1,2-Unsaturated pyrrolizidine alkaloids were converted into the common necin backbone structures and were analyzed and quantified by GC-MS in the selected ion monitoring mode.All but one medical honey analyzed were pyrrolizidine alkaloid positive. The results ranged from 10.6 µg retronecine equivalents per kg to 494.5 µg retronecine equivalents/kg medical honey. The average pyrrolizidine alkaloid content of all positive samples was 83.6 µg retronecine equivalents/kg medical honey (average of all samples was 79.3 µg retronecine equivalents/kg medical honey). The limit of detection was 2.0 µg retronecine equivalents/kg medical honey, while the limit of quantification was 6.0 µg retronecine equivalents/kg medical honey (S/N > 7/1).Based on the data presented here and considering the fact that medical honeys can be applied to open wounds, it seems reasonable to discuss the monitoring of 1,2-unsaturated pyrrolizidine alkaloids in honey intended for wound treatment. Georg Thieme Verlag KG Stuttgart · New York.

  2. Importance of Pyrrolizidine Alkaloids in Bee Products

    OpenAIRE

    OZANSOY, GÖRKEM; KÜPLÜLÜ, ÖZLEM

    2017-01-01

    Pyrrolizidinealkaloids are one of the groups of harmful chemicals of plants, which arenatural toxins. Pyrrolizidine alkaloids found in about 3% of all floweringplants of widespread geographical distribution are known as one of thecomponents of the hepatotoxic group of plant origin and referred as hepatotoxicpyrrolizidine alkaloids. According to researches, bee products is regarded asone of the main food sources in the exposure of people to pyrrolizidinealkaloids. Consumption of pyrrolizidine ...

  3. Nerinine and homolycorine, amaryllidaceae alkaloids from the bulbs of Galanthus transcaucasicus Fomin

    Directory of Open Access Journals (Sweden)

    M. Babashpour-Asl

    2017-01-01

    Full Text Available Background and objectives: Many members of the Amaryllidaceae are regarded as toxic. The toxic constituents that occur in the whole family are referred to as the Amaryllidaceae alkaloids. The main aim of this study was the identification of alkaloid compounds from Galanthus transcaucasicus Fomin, a medicinal plant from Amaryllidaceae. Methods: Planar and column chromatography techniques were used for isolation of alkaloid components. GC/MS analysis was carried out for the identification of alkaloid compounds. Results: Silica gel column chromatography of the alkaloidal extract of G. transcaucasicus bulbs afforded seven fractions. Preparative thin layer chromatography of these fractions led to the isolation of compounds 1 (nerinineand 2 (homolycorine. Galantamine was not detected in any of these fractions. Conclusion: Our findings showed that G. transcaucasicus could be a new source of bioactive alkaloids for possible applications in pharmaceutical industries.

  4. Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae).

    Science.gov (United States)

    Boppré, Michael; Colegate, Steven M

    2015-01-01

    The freshwater aquatic plant Gymnocoronis spilanthoides (Senegal tea plant, jazmín del bañado, Falscher Wasserfreund) is an invasive plant in many countries. Behavioural observations of pyrrolizidine alkaloid-pharmacophagous butterflies suggested the presence of pyrrolizidine alkaloids in the plant. To determine whether the attraction of the butterflies to the plant is an accurate indicator of pyrrolizidine alkaloids in G. spilanthoides. The alkaloid fraction of a methanolic extract of G. spilanthoides was analysed using HPLC with electrospray ionisation MS and MS/MS. Two HPLC approaches were used, that is, a C18 reversed-phase column with an acidic mobile phase, and a porous graphitic carbon column with a basic mobile phase. Pyrrolizidine alkaloids were confirmed, with the free base forms more prevalent than the N-oxides. The major alkaloids detected were lycopsamine and intermedine. The porous graphitic carbon HPLC column, with basic mobile phase conditions, resulted in better resolution of more pyrrolizidine alkaloids including rinderine, the heliotridine-based epimer of intermedine. Based on the MS/MS and high-resolution MS data, gymnocoronine was tentatively identified as an unusual C9 retronecine ester with 2,3-dihydroxy-2-propenylbutanoic acid. Among several minor-abundance monoester pyrrolizidines recognised, spilanthine was tentatively identified as an ester of isoretronecanol with the unusual 2-acetoxymethylbutanoic acid. The butterflies proved to be reliable indicators for the presence of pro-toxic 1,2-dehydropyrrolizidine alkaloids in G. spilanthoides, the first aquatic plant shown to produce these alkaloids. The presence of the anti-herbivory alkaloids may contribute to the plant's invasive capabilities and would certainly be a consideration in any risk assessment of deliberate utilisation of the plant. The prolific growth of the plant and the structural diversity of its pyrrolizidine alkaloids may make it ideal for investigating biosynthetic

  5. Writing Inspired

    Science.gov (United States)

    Tischhauser, Karen

    2015-01-01

    Students need inspiration to write. Assigning is not teaching. In order to inspire students to write fiction worth reading, teachers must take them through the process of writing. Physical objects inspire good writing with depth. In this article, the reader will be taken through the process of inspiring young writers through the use of boxes.…

  6. Analogue Gravity

    Directory of Open Access Journals (Sweden)

    Barceló Carlos

    2005-12-01

    Full Text Available Analogue models of (and for gravity have a long and distinguished history dating back to the earliest years of general relativity. In this review article we will discuss the history, aims, results, and future prospects for the various analogue models. We start the discussion by presenting a particularly simple example of an analogue model, before exploring the rich history and complex tapestry of models discussed in the literature. The last decade in particular has seen a remarkable and sustained development of analogue gravity ideas, leading to some hundreds of published articles, a workshop, two books, and this review article. Future prospects for the analogue gravity programme also look promising, both on the experimental front (where technology is rapidly advancing and on the theoretical front (where variants of analogue models can be used as a springboard for radical attacks on the problem of quantum gravity.

  7. Simultaneous determination of the content of isoquinoline alkaloids in Dicranostigma leptopodum (Maxim) Fedde and the effective fractionation of the alkaloids by high-performance liquid chromatography with diode array detection.

    Science.gov (United States)

    Chen, Yali; Li, Min; Liu, Jianjun; Yan, Qian; Zhong, Mei; Liu, Junxi; Di, Duolong; Liu, Jinxia

    2015-01-01

    A simple and efficient method was developed for the simultaneous determination of eight isoquinoline alkaloids in methanol extracts of Dicranostigma leptopodum (Maxim) Fedde and the effective fractionation of the alkaloids of D. leptopodum by high-performance liquid chromatography with diode array detection. The chromatographic conditions were optimized on a SinoChrom ODS-BP column to obtain a good separation of the four types of alkaloid analytes, including two aporphines (isocorydine, corydine), two protopines (protopine and allocryptopine), a morphine (sinoacutine), and three quaternary protoberberine alkaloids (berberrubine, 5-hydroxycoptisine, and berberine). The separation of these alkaloids was significantly affected by the composition of the mobile phase, and particularly by its pH value. Acetonitrile (A) and 0.2% phosphoric acid solution adjusted to pH 6.32 with triethylamine (B) were selected as the mobile phase with a gradient elution. With this method, a new quaternary protoberberine alkaloid was isolated and the two structural isomers (isocorydine and corydine) were baseline separated. The appropriate harvest period for D. leptopodum was also recommended based on our analysis. The method for the effective fraction of the alkaloids of D. leptopodum was optimized under this method with regard to the varying significant pharmacological activities of the alkaloids. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. Heterosis and heritability estimates of purine alkaloids and ...

    African Journals Online (AJOL)

    Dry cocoa beans displayed high content of purine alkaloids (2.1 and 8.8 mg g-1 for caffein and theobromine, respectively), and polyphenols (25 and 2978 μg g-1 for catechin and epicatechin, respectively). Among the five cocoa clones, SNK16 was the highest in purine alkaloid (caffein and theobromin) and flavanol ...

  9. Pyrrolizidine alkaloids in medicinal tea of Ageratum conyzoides

    Directory of Open Access Journals (Sweden)

    Cristiane F. Bosi

    2013-06-01

    Full Text Available It is now widely-recognized that the view that herbal remedies have no adverse effects and/or toxicity is incorrect; some traditionally-used plants can present toxicity. The well-established popular use of Ageratum conyzoides has led to its inclusion in a category of medicinal crude drugs created by the Brazilian Health Surveillance Agency. Ageratum belongs to the Eupatorieae tribe, Asteraceae, and is described as containing toxic pyrrolizidine alkaloids. Aqueous extracts of Ageratum conyzoides L. harvested in Brazil (commercial, flowering and non-flowering samples were prepared according to the prescribed method and analyzed by HPLC-HRMS. The pyrrolizidine alkaloids lycopsamine, dihydrolycopsamine, and acetyl-lycopsamine and their N-oxides, were detected in the analyzed extracts, lycopsamine and its N-oxide being known hepatotoxins and tumorigens. Together with the pyrrolizidine alkaloids identified by HPLC-HRMS, thirteen phenolic compounds were identified, notably, methoxylated flavonoids and chromenes. Toxicological studies on A. conyzoides are necessary, as is monitoring of its clinical use. To date, there are no established safety guidelines on pyrrolizidine alkaloids-containing plants, and their use in Brazil.

  10. Pyrrolizidine alkaloids in medicinal tea of Ageratum conyzoides

    Directory of Open Access Journals (Sweden)

    Cristiane F. Bosi

    2013-03-01

    Full Text Available It is now widely-recognized that the view that herbal remedies have no adverse effects and/or toxicity is incorrect; some traditionally-used plants can present toxicity. The well-established popular use of Ageratum conyzoides has led to its inclusion in a category of medicinal crude drugs created by the Brazilian Health Surveillance Agency. Ageratum belongs to the Eupatorieae tribe, Asteraceae, and is described as containing toxic pyrrolizidine alkaloids. Aqueous extracts of Ageratum conyzoides L. harvested in Brazil (commercial, flowering and non-flowering samples were prepared according to the prescribed method and analyzed by HPLC-HRMS. The pyrrolizidine alkaloids lycopsamine, dihydrolycopsamine, and acetyl-lycopsamine and their N-oxides, were detected in the analyzed extracts, lycopsamine and its N-oxide being known hepatotoxins and tumorigens. Together with the pyrrolizidine alkaloids identified by HPLC-HRMS, thirteen phenolic compounds were identified, notably, methoxylated flavonoids and chromenes. Toxicological studies on A. conyzoides are necessary, as is monitoring of its clinical use. To date, there are no established safety guidelines on pyrrolizidine alkaloids-containing plants, and their use in Brazil.

  11. Calcium, membranes and accumulation of alkaloids in plants

    International Nuclear Information System (INIS)

    Lovkova, M.Ya.; Buzuk, G.N.; Grinkevich, N.I.

    1983-01-01

    Ca 2+ effect upon metabolism of aporphines and protopines has been studied in Glaucium flavun, which alkaloids are of an essential interest for the medicine practice. It has been shown that calcium produces the inhibiting effect both on catabolitic splitting and metabolism of glaucine and protopine. It has been anticipated that calcuium introduced into an expert plant stabilizes membranes of intracellular structures and prevents 14 C alkaloid entering from an environment to metabolically active cell compartments, which contain ferments realizing transformations of the above compounds. The level of membrane permeability is probably the main mechanism, through which a control of metabolism processes occurs, and hence, a control of alkaloid accumulation processes under in vivo conditions

  12. Occurrence of theobromine synthase genes in purine alkaloid-free species of Camellia plants.

    Science.gov (United States)

    Ishida, Mariko; Kitao, Naoko; Mizuno, Kouichi; Tanikawa, Natsu; Kato, Misako

    2009-02-01

    Caffeine (1,3,7-trimethylxanthine) and theobromine (3,7-dimethylxanthine) are purine alkaloids that are present in high concentrations in plants of some species of Camellia. However, most members of the genus Camellia contain no purine alkaloids. Tracer experiments using [8-(14)C]adenine and [8-(14)C]theobromine showed that the purine alkaloid pathway is not fully functional in leaves of purine alkaloid-free species. In five species of purine alkaloid-free Camellia plants, sufficient evidence was obtained to show the occurrence of genes that are homologous to caffeine synthase. Recombinant enzymes derived from purine alkaloid-free species showed only theobromine synthase activity. Unlike the caffeine synthase gene, these genes were expressed more strongly in mature tissue than in young tissue.

  13. New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture.

    Science.gov (United States)

    Sheludko, Yuri; Gerasimenko, Irina; Kolshorn, Heinz; Stöckigt, Joachim

    2002-07-01

    Three new monoterpenoid indole alkaloids, 19(S),20(R)-dihydroperaksine (1), 19(S),20(R)-dihydroperaksine-17-al (2), and 10-hydroxy-19(S),20(R)-dihydroperaksine (3), along with 16 known alkaloids 4-19 were isolated from hairy root culture of Rauvolfia serpentina, and their structures were elucidated by 1D and 2D NMR analyses. Taking into account the stereochemistry of the new alkaloids and results of preliminary enzymatical studies, the putative biosynthetical relationships between the novel alkaloids are discussed.

  14. Combining Bio-inspired Sensing with Bio-inspired Locomotion

    DEFF Research Database (Denmark)

    Shaikh, Danish; Hallam, John; Christensen-Dalsgaard, Jakob

    In this paper we present a preliminary Braitenberg vehicle–like approach to combine bio-inspired audition with bio-inspired quadruped locomotion in simulation. Locomotion gaits of the salamander–like robot Salamandra robotica are modified by a lizard’s peripheral auditory system model that modula......In this paper we present a preliminary Braitenberg vehicle–like approach to combine bio-inspired audition with bio-inspired quadruped locomotion in simulation. Locomotion gaits of the salamander–like robot Salamandra robotica are modified by a lizard’s peripheral auditory system model...

  15. [Comparative study on alkaloids of tissue-culture seedling and wild plant of Dendrobium huoshanense ].

    Science.gov (United States)

    Chen, Nai-dong; Gao, Feng; Lin, Xin; Jin, Hui

    2014-06-01

    To compare the composition and content of alkaloid of Dendrobium huoshanense tissue-culture seedling and wild plant. A comparative evaluation on the quality was carried out by HPLC and TLC methods including the composition and the content of alkaloids. Remarkable variation existed in the two kinds of Dendrobium huoshanense. For the tissue-culture plant, only two alkaloids were checked out by both HPLC and TLC while four alkaloids were observed in the wild plant. The alkaloid content of tissue-culture seedling and wild plant was(0. 29 ± 0. 11)%o and(0. 43 ± 0. 15) %o,respectively. Distinguished difference is observed in both composition and content of alkaloids from the annual shoots of different provenances of Dendrobium huoshanense. It suggested that the quality of tissue-culture seedling of Dendrobium huoshanense might be inconsistent with the wild plant. Furthermore, the established alkaloids-knock-out HPLC method would provide a new research tool on quality control of Chinese medicinal materials which contain unknown alkaloids.

  16. Alkaloids in the human food chain - Natural occurrence and possible adverse effects

    NARCIS (Netherlands)

    Koleva, I.; Beek, van T.A.; Soffers, A.E.M.F.; Dusemund, B.; Rietjens, I.

    2012-01-01

    Alkaloid-containing plants are an intrinsic part of the regular Western diet. The present paper summarizes the occurrence of alkaloids in the food chain, their mode of action and possible adverse effects including a safety assessment. Pyrrolizidine alkaloids are a reason for concern because of their

  17. Pyrrolizidine alkaloids from seven wild-growing Senecio species in Serbia and Montenegro

    Directory of Open Access Journals (Sweden)

    BORIS M. MANDIC

    2009-01-01

    Full Text Available The genus Senecio (family Asteraceae is one of the largest in the world. It comprises about 1100 species which are the rich source of pyrrolizidine alkaloids. Plants containing pyrrolizidine alkaloids are among the most important sources of human and animal exposure to plant toxins and carcinogens. The pyrrolizidine alkaloids of seven Senecio species (S. erucifolius, S. othonnae, S. wagneri, S. subalpinus, S. carpathicus, S. paludosus and S. rupestris were studied. Fourteen alkaloids were isolated and their structures determined from spectroscopic data (1H- and 13C-NMR, IR and MS. Five of them were identified in S. erucifolius, four in S. othonnae, two in S. wagneri, four in S. subalpinus, two in S. carpathicus, three in S. paludosus and three in S. rupestris. Seven pyrrolizidine alkaloids were found for the first time in particular species. The results have chemotaxonomic importance. The cytotoxic activity and antimicrobial activity of some alkaloids were also studied.

  18. Pharmacological actions of Uncaria alkaloids, rhynchophylline and isorhynchophylline.

    Science.gov (United States)

    Shi, Jing-Shan; Yu, Jun-Xian; Chen, Xiu-Ping; Xu, Rui-Xia

    2003-02-01

    The pharmacological actions of Uncaria alkaloids, rhynchophylline and isorhynchophylline extracted from Uncaria rhynchophylla Miq Jacks were reviewed. The alkaloids mainly act on cardiovascular system and central nervous system including the hypotension, brachycardia, antiarrhythmia, and protection of cerebral ischemia and sedation. The active mechanisms were related to blocking of calcium channel, opening of potassium channel, and regulating of nerve transmitters transport and metabolism, etc.

  19. Pro-toxic dehydropyrrolizidine alkaloids in the traditional Andean herbal medicine “asmachilca”

    Science.gov (United States)

    Colegate, Steven M.; Boppré, Michael; Monzón, Julio; Betz, Joseph M.

    2015-01-01

    Ethnopharmacological relevance Asmachilca is a Peruvian medicinal herb preparation ostensibly derived from Eupatorium gayanum Wedd. = Aristeguietia gayana (Wedd.) R.M. King & H. Rob. (Asteraceae: Eupatorieae). Decoctions of the plant have a reported bronchodilation effect that is purported to be useful in the treatment of respiratory allergies, common cold and bronchial asthma. However, its attractiveness to pyrrolizidine alkaloid-pharmacophagous insects indicated a potential for toxicity for human consumers. Aim of the study To determine if commercial asmachilca samples, including fully processed herbal teas, contain potentially toxic 1,2-dehydropyrrolizidine alkaloids. Materials and methods Two brands of “Asmachilca” herbal tea bags and four other commercial samples of botanical materials for preparing asmachilca medicine were extracted and analyzed using HPLC-esi(+)MS and MS/MS for the characteristic retention times and mass spectra of known dehydropyrrolizidine alkaloids. Other suspected dehydropyrrolizidine alkaloids were tentatively identified based on MS/MS profiles and high resolution molecular weight determinations. Further structure elucidation of isolated alkaloids was based on 1D and 2D NMR spectroscopy. Results Asmachilca attracted many species of moths which are known to pharmacophagously gather dehydropyrrolizidine alkaloids. Analysis of 5 of the asmachilca samples revealed the major presence of the dehydropyrrolizidine alkaloid monoesters rinderine and supinine, and their N-oxides. The 6th sample was very similar but did not contain supinine or its N-oxide. Small quantities of other dehydropyrrolizidine alkaloid monoesters, including echinatine and intermedine, were also detected. In addition, two major metabolites, previously undescribed, were isolated and identified as dehydropyrrolizidine alkaloid monoesters with two “head-to-tail” linked viridifloric and/or trachelanthic acids. Estimates of total pyrrolizidine alkaloid and N

  20. [Recent results on the pharmacodynamics of Strychnos malgaches alkaloids].

    Science.gov (United States)

    Rasoanaivo, P; Ratsimamanga-Urverg, S; Frappier, F

    1996-01-01

    Investigation of Strychnos (Loganiaceae) shrubs and trees was initiated by their traditional uses of their inherent poisons on arrows: this led to the discovery of strychnine and curare alkaloids. Subsequently, phytochemical investigation of several Strychnos species has shown great structural diversity of the alkaloid constituent which also display various biological effects, i.e. convulsive and relaxant effects on muscles, and antimicrobial, antitumor and antihypertensive properties. Ethnobotanical field work conducted in different regions of Madagascar revealed that infusion of three Strychnos species, S. mostueoides, S. myrtoides and S. diplotricha, is used in association with subcurative doses of chloroquine to treat chronic malaria. Bioassayfractionation led to the isolation of two major bioactive components, strychnobrasiline and malagashanine. Whereas strychnobrasiline is a previously known chemical compound, malagashanine is the first in a series of a new subtype of Strychnos alkaloids. These two alkaloids are devoid of intrinsic antimalarial effects, both in vitro (IC50 = 73.0 micrograms/ml for strychnobrasiline and 69.1 micrograms/ml for malagashanine) and in vivo (10 mg/kg conferred a 5% suppression of parasitemia). When these alkaloids are combined with chloroquine at doses much lower than required for antiplasmodial effects, they greatly enhance the chloroquine action in a dose dependent manner as seen by the isobologram method. Several minor alkaloids structurally related to malagashanine were also isolated from Madagascan Strychnos. They all enhance, to greater or lesser degrees, the chloroquine effectiveness. Interestingly, there is a positive correlation between the ethnomedical use of the three Strychnos species as chloroquine adjuvants and the chloroquine-potentiating effects of malagashanine and strychnobrasiline isolated from them. After preliminary toxicological studies, infusion of stem barks of S. myrtoides in association with chloroquine

  1. The expanding universe of alkaloid biosynthesis.

    Science.gov (United States)

    De Luca, V; Laflamme, P

    2001-06-01

    Characterization of many of the major gene families responsible for the generation of central intermediates and for their decoration, together with the development of large genomics and proteomics databases, has revolutionized our capability to identify exotic and interesting natural-product pathways. Over the next few years, these tools will facilitate dramatic advances in our knowledge of the biosynthesis of alkaloids, which will far surpass that which we have learned in the past 50 years. These tools will also be exploited for the rapid characterization of regulatory genes, which control the development of specialized cell factories for alkaloid biosynthesis.

  2. Analytical chemical study of alkaloid fraction of methanolic extract of Croton baillonianus (AUBL) leaves

    International Nuclear Information System (INIS)

    Fuertes R, Cesar M.; Benavides, Angelyne; Pizza, Cosimo; Napolitano, Asunta; Basarello, Carla; Piacente, Sonia; Carbone Virginia

    2012-01-01

    The objective of the present study has been to extract and isolate the alkaloids from leaves of Croton baillonianus, corresponding to the methanolic extract by exclusion chromatography with Sephadex LH-20 followed by a purification by high performance liquid chromatography, obtaining six alkaloids. Two low polarity alkaloid and two glycoside alkaloids were analyzed by Electronic System impact mass spectrometry; these alkaloids belong to bencylisoquinolinic type; the study has connection to the determination of its antioxidant, antiulcerose and cytotoxic properties. (author).

  3. Spiro[pyrrolidine-3,3′-oxindoles] and Their Indoline Analogues as New 5-HT6 Receptor Chemotypes

    Directory of Open Access Journals (Sweden)

    Ádám A. Kelemen

    2017-12-01

    Full Text Available Synthetic derivatives of spiro[pyrrolidinyl-3,3′-oxindole] alkaloids (coerulescine analogues were investigated as new ligands for aminergic G-protein coupled receptors (GPCRs. The chemical starting point 2′-phenylspiro[indoline-3,3′-pyrrolidin]-2-one scaffold was identified by virtual fragment screening utilizing ligand- and structure based methods. As a part of the hit-to-lead optimization a structure-activity relationship analysis was performed to explore the differently substituted 2′-phenyl-derivatives, introducing the phenylsulphonyl pharmacophore and examining the corresponding reduced spiro[pyrrolidine-3,3′-indoline] scaffold. The optimization process led to ligands with submicromolar affinities towards the 5-HT6 receptor that might serve as viable leads for further optimization.

  4. Synthesis and evaluation of anticancer natural product analogues based on angelmarin: targeting the tolerance towards nutrient deprivation.

    Science.gov (United States)

    Magolan, Jakob; Adams, Nathan B P; Onozuka, Hiroko; Hungerford, Natasha L; Esumi, Hiroyasu; Coster, Mark J

    2012-05-01

    Inspired by nature: Angelmarin is an anticancer natural product with potent antiausterity activity, that is, selective cytotoxicity towards nutrient-deprived, resistant cancer cells. Through structure-activity relationship studies, three analogues were identified as lead compounds for the develpoment of molecular probes for the investigation of the mode of action and biological targets of the antiausterity compounds. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. A new strain of Claviceps purpurea accumulating tetracyclic clavine alkaloids.

    Science.gov (United States)

    Schumann, B; Erge, D; Maier, W; Gröger, D

    1982-05-01

    A new strain of Claviceps was isolated from a blokked mutant of Claviceps purpurea. This strain accumulates substantial amounts of clavine alkaloids (2 g/l). The alkaloid fraction is composed of chanoclavine-I ( approximately 10%) and a mixture of agroclavine/elymoclavine (90%). Most suitable for alkaloid production in submerged culture is an ammoncitrate/sucrose medium. The genealogy of the new strain, designated Pepty 695/ch-I is the following one: Pepty 695/S (ergotoxine producer) --> Pepty 695/ch (secoergoline producer) --> Pepty 695/ch-I (tetracyclic clavine producer).

  6. An experimental study of radioprotective effect of ginseng alkaloid fraction on cellular damage

    Energy Technology Data Exchange (ETDEWEB)

    Yoo, Seong Yul; Cho, Chul Koo; Kim, Mi Sook; Yoo, Hyung Jun; Kim, Seong Ho; Kim, Tae Hwan [Korea Cancer Center Hospital, Seoul (Korea, Republic of)

    1997-09-01

    This paper is to assess the effect of Adaptagen as a radioprotector in which main component is alkaloid fraction of ginseng. Evaluation was made in vitro and in vivo study with NIGP(S) mouse by the measurement of regeneration of jejunal crypt cell and micronucleus assay to analyze radioprotective effect of ginseng alkaloid fraction in comparison with that of water fraction after whole body irradiation. The results were as follows, 1. The degree of radiation damage of mouse jejunal crypt cell was diminished in both of alkaloid and water fraction groups compared to control group but more in alkaloid fraction group than water fraction group. 2. Regeneration of mouse jejunal crypt cell was higher both in alkaloid and water fraction groups than control group. 3. In vitro study, frequency of micronucleus was diminished in tendency for the treated groups than control group but statistically insignificant. 4. In vitro study, frequency of micronucleus was diminished in both alkaloid and water fraction groups compared to control group but more in alkaloid fraction group than water fraction group.

  7. Cyclobutane-Containing Alkaloids: Origin, Synthesis, and Biological Activities

    OpenAIRE

    Sergeiko, Anastasia; Poroikov, Vladimir V; Hanuš, Lumir O; Dembitsky, Valery M

    2008-01-01

    Present review describes research on novel natural cyclobutane-containing alkaloids isolated from terrestrial and marine species. More than 60 biological active compounds have been confirmed to have antimicrobial, antibacterial, antitumor, and other activities. The structures, synthesis, origins, and biological activities of a selection of cyclobutane-containing alkaloids are reviewed. With the computer program PASS some additional biological activities are also predicted, which point toward ...

  8. Comparative toxicity of coniine, an alkaloid of Conium maculatum (poison hemlock), in chickens, quails, and turkeys.

    Science.gov (United States)

    Frank, A A; Reed, W M

    1990-01-01

    Coniine, an alkaloid of Conium maculatum (poison hemlock), was administered by gavage to immature chickens, quails, and turkeys at 0, 25, 50, and 100 mg/kg body weight. At 25 mg coniine/kg body weight, clinical signs were observed only in quails (2/10) and consisted of excitement, depression, hypermetria, seizures, opisthotonos, and flaccid paralysis. Chickens (9/10) and quails (8/10) dosed at 50 mg/kg body weight were affected, and several birds of each species died (2/10 and 5/10, respectively). Turkeys (7/10) were affected only when dosed at 100 mg/kg body weight, and quails (6/10), turkeys (4/10), and chickens (10/10) died at this dose. There were no gross or microscopic lesions. Coniine was detected in skeletal muscle and liver of birds dying after ingestion and was present in some survivors 7 days post-treatment.

  9. Mass-spectrometry-directed analysis and purification of pyrrolizidine alkaloid cis/trans isomers in Gynura japonica.

    Science.gov (United States)

    Fang, Lianxiang; Xiong, Aizhen; Yang, Xiao; Cheng, Wenzhi; Yang, Li; Wang, Zhengtao

    2014-08-01

    Pyrrolizidine alkaloids are highly hepatotoxic natural chemicals that produce irreversible chronic and acute hepatotoxic effects on human beings. Purification of large amounts of pyrrolizidine alkaloids is necessary for toxicity studies. In this study, an efficient method for targeted analysis and purification of pyrrolizidine alkaloid cis/trans isomers from herbal materials was developed for the first time. Targeted analysis of the hepatotoxic pyrrolizidine alkaloids was performed by liquid chromatography with tandem mass spectrometry (precursor ion scan and daughter ion scan), and the purification of pyrrolizidine alkaloids was achieved with a mass-directed auto purification system. The extraction and preparative liquid chromatography conditions were optimized. The developed method was applied to analysis of Gynura japonica (Thunb.) Juel., a herbal medicine traditionally used for detumescence and relieving pain but is potentially hepatotoxic as it contains pyrrolizidine alkaloids. Twelve pyrrolizidine alkaloids (six cis/trans isomer pairs) were identified with reference compounds or characterized by liquid chromatography with tandem mass spectrometry, and five individual pyrrolizidine alkaloids, including (E)-seneciphylline, seneciphylline, integerrimine, senecionine, and seneciphyllinine, were prepared from G. japonica roots with high efficiency. The results of this work provide a new technique for the preparation of large amounts of pyrrolizidine alkaloid reference substances, which will also benefit toxicological studies of pyrrolizidine alkaloids and treatments for pyrrolizidine alkaloid-induced toxicity. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Histrionicotoxin alkaloids finally detected in an ant

    DEFF Research Database (Denmark)

    Jones, Tappey H.; Adams, Rachelle Martha Marie; Spande, Thomas F.

    2012-01-01

    Workers of the ant Carebarella bicolor collected in Panama were found to have two major poison-frog alkaloids, cis- and trans-fused decahydroquinolines (DHQs) of the 269AB type, four minor 269AB isomers, two minor 269B isomers, and three isomers of DHQ 271D. For the first time in an ant, however......) sp., were found to have a very similar DHQ complex but failed to show HTXs. Several new DHQ alkaloids of MW 271 (named in the frog as 271G) are reported from the above ants that have both m/z 202 and 204 as major fragment ions, unlike the spectrum seen for the poison-frog alkaloid 271D, which has...... only an m/z 204 base peak. Found also for the first time in skin extracts from the comparison frog Oophaga granulifera of Costa Rica is a trace DHQ of MW 273. It is coded as 273F in the frog; a different isomer is found in the ant....

  11. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors.

    Science.gov (United States)

    Green, Benedict T; Lee, Stephen T; Panter, Kip E; Welch, Kevin D; Cook, Daniel; Pfister, James A; Kem, William R

    2010-01-01

    Teratogenic alkaloids are found in many species of plants including Conium maculatum L., Nicotiana glauca, Nicotiana tabaccum, and multiple Lupinus spp. Fetal musculoskeletal defects produced by alkaloids from these plants include arthrogyropisis, scoliosis, torticollis, kyposis, lordosis, and cleft palate. A pharmacodynamic comparison of the alkaloids ammodendrine, anabasine, anabaseine, anagyrine, and coniine in SH-SY5Y cells and TE-671 cells was made. These alkaloids and their enantiomers were more effective in depolarizing TE-671 cells which express the human fetal-muscle type nicotinic acetylcholine receptor (nAChR) relative to SH-SY5Y cells which predominately express autonomic nAChRs. The rank order of potency in TE-671 cells was: anabaseine>(+)-anabasine>(-)-anabasine > (+/-)-anabasine>anagyrine>(-)-coniine > (+/-)-coniine>(+)-coniine>(+/-)-ammodendrine>(+)-ammodendrine. The rank order potency in SH-SY5Y cells was: anabaseine>(+)-anabasine>(-)-coniine>(+)-coniine>(+)-ammodendrine>anagyrine>(-)-anabasine>(+/-)-coniine>(+/-)-anabasine>(-)-ammodendrine. The actions of these alkaloids at nAChRs in both cell lines could be distinguished by their maximum effects in depolarizing cell membrane potential. The teratogenic action of these compounds may be related to their ability to activate and subsequently desensitize nAChRs.

  12. Quinolizidine alkaloids from the curare adjuvant Clathrotropis glaucophylla.

    Science.gov (United States)

    Sagen, Anne Lise; Gertsch, Jürg; Becker, Rita; Heilmann, Jörg; Sticher, Otto

    2002-12-01

    The bark of Clathrotropis glaucophylla (Fabaceae) is used as admixture of curare arrow poison by the Yanomami; Amerindians in Venezuela. A new quinolizidine alkaloid (QA), (-)-13alpha-hydroxy-15alpha-(1-hydroxyethyl)-anagyrine [(-)-clathrotropine], was isolated from the alkaloid extract of C. glaucophylla bark, together with eleven known QAs: (-)-anagyrine, (-)-thermopsine, (-)-baptifoline, (-)-epibaptifoline, (-)-rhombifoline, (-)-tinctorine, (-)-cytisine, (-)-N-methylcytisine, (-)-lupanine, (-)-6alpha-hydroxylupanine and (+)-5,6-dehydrolupanine. The isolation and structure elucidation were performed with the aid of chromatographic (TLC, HPLC and CC) and spectroscopic (UV and 1D/2D NMR) methods, and mass spectrometry. To our knowledge, this is the first time quinolizidine alkaloids have been isolated from an arrow poison ingredient. It is also the first report on Clathrotropis species being used for preparation of arrow poison.

  13. Indolopyridoquinazoline alkaloids from Esenbeckia grandiflora mart. (Rutaceae); Alkaloides {beta}-indolopiridoquinazolinicos de Esenbeckia grandiflora mart. (Rutaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Januario, Ana Helena; Vieira, Paulo Cezar; Silva, Maria Fatima das Gracas Fernandes da; Fernandes, Joao Batista [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica], e-mail: anahjanuario@unifran.br; Silva, Jorge Jose de Brito; Conserva, Lucia Maria [Universidade Federal de Alagoas (UFAL), Maceio, AL (Brazil). Inst. de Quimica e Biotecnologia

    2009-07-01

    The chemical composition of two specimens of Esenbeckia grandiflora, collected in the south and northeast regions of Brazil, was investigated. In this study, three b-indolopyridoquinazoline alkaloids from the leaves (rutaecarpine, 1-hydroxyrutaecarpine) and roots (euxylophoricine D) were isolated for the first time in this genus. In addition, the triterpenes {alpha}-amyrin, {beta}-amyrin, {alpha}-amyrenonol, {beta}-amyrenonol, 3{alpha}-hydroxy-ursan-12-one, and 3{alpha}-hydroxy-12,13-epoxy-oleanane, the coumarins auraptene, umbelliferone, pimpinelin, and xanthotoxin, the furoquinoline alkaloids delbine and kokusaginine, and the phytosteroids sitosterol, stigmasterol, campesterol and 3{beta}-O-{beta}-D-glucopyranosylsitosterol were also isolated from the leaves, twigs, roots and stems of this species. Structures of these compounds were established by spectral analysis. (author)

  14. Currencies of Mutualisms: Sources of Alkaloid Genes in Vertically Transmitted Epichloae

    Directory of Open Access Journals (Sweden)

    Christopher L. Schardl

    2013-06-01

    Full Text Available The epichloae (Epichloë and Neotyphodium species, a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae. Most epichloae are vertically transmitted in seeds (endophytes, and most produce alkaloids that attack nervous systems of potential herbivores. These protective metabolites include ergot alkaloids and indole-diterpenes (tremorgens, which are active in vertebrate systems, and lolines and peramine, which are more specific against invertebrates. Several Epichloë species have been described which are sexual and capable of horizontal transmission, and most are vertically transmissible also. Asexual epichloae are mainly or exclusively vertically transmitted, and many are interspecific hybrids with genomic contributions from two or three ancestral Epichloë species. Here we employ genome-scale analyses to investigate the origins of biosynthesis gene clusters for ergot alkaloids (EAS, indole-diterpenes (IDT, and lolines (LOL in 12 hybrid species. In each hybrid, the alkaloid-gene and housekeeping-gene relationships were congruent. Interestingly, hybrids frequently had alkaloid clusters that were rare in their sexual ancestors. Also, in those hybrids that had multiple EAS, IDT or LOL clusters, one cluster lacked some genes, usually for late pathway steps. Possible implications of these findings for the alkaloid profiles and endophyte ecology are discussed.

  15. Currencies of Mutualisms: Sources of Alkaloid Genes in Vertically Transmitted Epichloae

    Science.gov (United States)

    Schardl, Christopher L.; Young, Carolyn A.; Pan, Juan; Florea, Simona; Takach, Johanna E.; Panaccione, Daniel G.; Farman, Mark L.; Webb, Jennifer S.; Jaromczyk, Jolanta; Charlton, Nikki D.; Nagabhyru, Padmaja; Chen, Li; Shi, Chong; Leuchtmann, Adrian

    2013-01-01

    The epichloae (Epichloë and Neotyphodium species), a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae). Most epichloae are vertically transmitted in seeds (endophytes), and most produce alkaloids that attack nervous systems of potential herbivores. These protective metabolites include ergot alkaloids and indole-diterpenes (tremorgens), which are active in vertebrate systems, and lolines and peramine, which are more specific against invertebrates. Several Epichloë species have been described which are sexual and capable of horizontal transmission, and most are vertically transmissible also. Asexual epichloae are mainly or exclusively vertically transmitted, and many are interspecific hybrids with genomic contributions from two or three ancestral Epichloë species. Here we employ genome-scale analyses to investigate the origins of biosynthesis gene clusters for ergot alkaloids (EAS), indole-diterpenes (IDT), and lolines (LOL) in 12 hybrid species. In each hybrid, the alkaloid-gene and housekeeping-gene relationships were congruent. Interestingly, hybrids frequently had alkaloid clusters that were rare in their sexual ancestors. Also, in those hybrids that had multiple EAS, IDT or LOL clusters, one cluster lacked some genes, usually for late pathway steps. Possible implications of these findings for the alkaloid profiles and endophyte ecology are discussed. PMID:23744053

  16. Currencies of mutualisms: sources of alkaloid genes in vertically transmitted epichloae.

    Science.gov (United States)

    Schardl, Christopher L; Young, Carolyn A; Pan, Juan; Florea, Simona; Takach, Johanna E; Panaccione, Daniel G; Farman, Mark L; Webb, Jennifer S; Jaromczyk, Jolanta; Charlton, Nikki D; Nagabhyru, Padmaja; Chen, Li; Shi, Chong; Leuchtmann, Adrian

    2013-06-06

    The epichloae (Epichloë and Neotyphodium species), a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae). Most epichloae are vertically transmitted in seeds (endophytes), and most produce alkaloids that attack nervous systems of potential herbivores. These protective metabolites include ergot alkaloids and indole-diterpenes (tremorgens), which are active in vertebrate systems, and lolines and peramine, which are more specific against invertebrates. Several Epichloë species have been described which are sexual and capable of horizontal transmission, and most are vertically transmissible also. Asexual epichloae are mainly or exclusively vertically transmitted, and many are interspecific hybrids with genomic contributions from two or three ancestral Epichloë species. Here we employ genome-scale analyses to investigate the origins of biosynthesis gene clusters for ergot alkaloids (EAS), indole-diterpenes (IDT), and lolines (LOL) in 12 hybrid species. In each hybrid, the alkaloid-gene and housekeeping-gene relationships were congruent. Interestingly, hybrids frequently had alkaloid clusters that were rare in their sexual ancestors. Also, in those hybrids that had multiple EAS, IDT or LOL clusters, one cluster lacked some genes, usually for late pathway steps. Possible implications of these findings for the alkaloid profiles and endophyte ecology are discussed.

  17. Synthesis of Lycodine-Type Lycopodium Alkaloids Using C-H Functionalization Tactics

    OpenAIRE

    Newton, James

    2015-01-01

    This dissertation describes our syntheses of several lycodine-type Lycopodium alkaloids by the late-stage C-H functionalization of lycodine derivatives. Lycodine-type alkaloids are well-known for their neurological activity. For example, huperzine A is a potent acetylcholinesterase inhibitor and the complanadine family of molecules has been shown to induce the secretion of Nerve Growth Factor. Due to these properties, lycodine-type alkaloids serve as interesting lead compounds for the deve...

  18. Inspired Responses

    Science.gov (United States)

    Steele, Carol Frederick

    2011-01-01

    In terms of teacher quality, Steele believes the best teachers have reached a stage she terms inspired, and that teachers move progressively through the stages of unaware, aware, and capable until the most reflective teachers finally reach the inspired level. Inspired teachers have a wide repertoire of teaching and class management techniques and…

  19. Manzamine alkaloids: isolation, cytotoxicity, antimalarial activity and SAR studies.

    Science.gov (United States)

    Ashok, Penta; Ganguly, Swastika; Murugesan, Sankaranarayanan

    2014-11-01

    The infectious disease Malaria is caused by different species of the genus Plasmodium. Resistance to quinoline antimalarial drugs and decreased susceptibility to artemisinin-based combination therapy have increased the need for novel antimalarial agents. Historically, natural products have been used for the treatment of infectious diseases. Identification of natural products and their semi-synthetic derivatives with potent antimalarial activity is an important method for developing novel antimalarial agents. Manzamine alkaloids are a unique group of β-carboline alkaloids isolated from various species of marine sponge displaying potent antimalarial activity against drug-sensitive and -resistant strains of Plasmodium. In this review, we demonstrate antimalarial potency, cytotoxicity and antimalarial SAR of manzamine alkaloids. Copyright © 2014 Elsevier Ltd. All rights reserved.

  20. Effects of benzylisoquinoline alkaloids on the larvae of polyphagous Lepidoptera.

    Science.gov (United States)

    Miller, James S; Feeny, Paul

    1983-06-01

    Six benzylisoquinoline alkaloids were fed to the larvae of three polyphagous Lepidoptera species: Hyphantria cunea, Spodoptera eridania, and Lymantria dispar. Exposure of last instar larvae to alkaloid-containing diets over a 24-h period resulted in reduced feeding rates and reduced growth efficiencies. Lymantria dispar larvae reared from eggs on alkaloid diets took longer to reach the fifth instar, attained lower larval weights, and showed reduced survivorship. The benzylisoquinolines tested were not equally effective as toxins or feeding inhibitors. Some produced dramatic effects while others produced no effects. The relative responses of the three caterpillar species to the six alkaloids were similar. Those benzylisoquinolines with a methylene-dioxyphenyl (1,3-benzodioxole) group were consistently the most toxic or repellent while laudanosine, a relatively simple benzylisoquinoline, was generally innocuous. Available host records indicate that benzylisoquinoline-containing plants are avoided by the larvae of these moth species.

  1. Australine, a pyrrolizidine alkaloid that inhibits amyloglucosidase and glycoprotein processing

    International Nuclear Information System (INIS)

    Tropea, J.E.; Molyneux, R.J.; Kaushal, G.P.; Pan, Y.T.; Mitchell, M.; Elbein, A.D.

    1989-01-01

    Australine is a polyhydroxylated pyrrolizidine alkaloid that was isolated from the seeds of the Australian tree Castanospermum australe and characterized by NMR and X-ray diffraction analysis. Since swainsonine and catanospermine are polyhydroxylated indolizidine alkaloids that inhibit specific glycosidases, the authors tested australine against a variety of exoglycosidases to determine whether it would inhibit any of these enzymes. This alkaloid proved to be a good inhibitor of the α-glucosidase amyloglucosidase (50% inhibition at 5.8 μM), but it did not inhibit β-glucosidase, α- or β-mannosidase, or α- or β-galactosidase. The inhibition of amyloglucosidase was of a competitive nature. Australine also inhibited the glycoprotein processing enzyme glucosidase I, but had only slight activity toward glucosidase II. When incubated with cultured cells, this alkaloid inhibited glycoprotein processing at the glucosidase I step and caused the accumulation of glycoproteins with Glc 3 Man 7-9 (GlcNAc) 2 -oligosaccharides

  2. Indole alkaloids from leaves and twigs of Rauvolfia verticillata.

    Science.gov (United States)

    Zhang, Bing-Jie; Peng, Lei; Wu, Zhi-Kun; Bao, Mei-Fen; Liu, Ya-Ping; Cheng, Gui-Guang; Luo, Xiao-Dong; Cai, Xiang-Hai

    2013-01-01

    Seven new indole alkaloids, rauverines A-G (1-7), and 19 known indole alkaloids were isolated from the leaves and twigs of Rauvolfia verticillata. All compounds showed no cytotoxicity against five human cancer cell lines, human myeloid leukemia (HL-60), hepatocellular carcinoma (SMMC-7721), lung cancer (A-549), breast cancer (MCF-7), and colon cancer (SW480) cells.

  3. Pyrrolizidine alkaloids from Bulgarian species of the genus Senecio

    Directory of Open Access Journals (Sweden)

    NADEZHDA KOSTOVA

    2006-12-01

    Full Text Available Nine Bulgarian species from the genus Senecio were studied phytochemically and/or by GC-MS analysis. Senecivernine-N-oxide was isolated and identified by spectral data for the first time. Different types of pyrrolizidine alkaloids were tested for cytotoxicity on murine lymphocytes. At a concentration of 100 µg/ml, the alkaloid retroisosenine showed immunosuppressive effect.

  4. Sequestered Alkaloid Defenses in the Dendrobatid Poison Frog Oophaga pumilio Provide Variable Protection from Microbial Pathogens.

    Science.gov (United States)

    Hovey, Kyle J; Seiter, Emily M; Johnson, Erin E; Saporito, Ralph A

    2018-03-01

    Most amphibians produce their own defensive chemicals; however, poison frogs sequester their alkaloid-based defenses from dietary arthropods. Alkaloids function as a defense against predators, and certain types appear to inhibit microbial growth. Alkaloid defenses vary considerably among populations of poison frogs, reflecting geographic differences in availability of dietary arthropods. Consequently, environmentally driven differences in frog defenses may have significant implications regarding their protection against pathogens. While natural alkaloid mixtures in dendrobatid poison frogs have recently been shown to inhibit growth of non-pathogenic microbes, no studies have examined the effectiveness of alkaloids against microbes that infect these frogs. Herein, we examined how alkaloid defenses in the dendrobatid poison frog, Oophaga pumilio, affect growth of the known anuran pathogens Aeromonas hydrophila and Klebsiella pneumoniae. Frogs were collected from five locations throughout Costa Rica that are known to vary in their alkaloid profiles. Alkaloids were isolated from individual skins, and extracts were assayed against both pathogens. Microbe subcultures were inoculated with extracted alkaloids to create dose-response curves. Subsequent spectrophotometry and cell counting assays were used to assess growth inhibition. GC-MS was used to characterize and quantify alkaloids in frog extracts, and our results suggest that variation in alkaloid defenses lead to differences in inhibition of these pathogens. The present study provides the first evidence that alkaloid variation in a dendrobatid poison frog is associated with differences in inhibition of anuran pathogens, and offers further support that alkaloid defenses in poison frogs confer protection against both pathogens and predators.

  5. Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

    Directory of Open Access Journals (Sweden)

    Assem El-Shazly

    2014-04-01

    Full Text Available Among the diversity of secondary metabolites which are produced by plants as means of defence against herbivores and microbes, pyrrolizidine alkaloids (PAs are common in Boraginaceae, Asteraceae and some other plant families. Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in herbivores and humans. Almost all genera of the family Boraginaceae synthesize and store this type of alkaloids. This review reports the available information on the present status (literature up to early 2014 of the pyrrolizidine alkaloids in the Boraginaceae and summarizes the topics structure, distribution, chemistry, chemotaxonomic significance, and biological properties.

  6. "SINCE I MUST PLEASE THOSE BELOW": HUMAN SKELETAL REMAINS RESEARCH AND THE LAW.

    Science.gov (United States)

    Holland, Thomas D

    2015-01-01

    The ethics of non-invasive scientific research on human skeletal remains are poorly articulated and lack a single, definitive analogue in western law. Laws governing invasive research on human fleshed remains, as well as bio-ethical principles established for research on living subjects, provide effective models for the establishment of ethical guidelines for non-invasive research on human skeletal remains. Specifically, non-invasive analysis of human remains is permissible provided that the analysis and collection of resulting data (1) are accomplished with respect for the dignity of the individual, (2) do not violate the last-known desire of the deceased, (3) do not adversely impact the right of the next of kin to perform a ceremonious and decent disposal of the remains, and (4) do not unduly or maliciously violate the privacy interests of the next of kin.

  7. Alkaloids in Solanum torvum Sw (Solanaceae): (With 2 Tables & 1 Figure)

    OpenAIRE

    Pérez-Amador, MC; Muñoz Ocotero, V; García Castañeda, JM; González Esquinca, AR

    2007-01-01

    A comparison was made between plants of Solanum torvum Sw that grow in Chiapas, Mexico, and plants of the same species originating from India. This was effected to establish either similarities or differences between these plants in total alkaloid contents and presence of solasodine, an important alkaloid for the partial synthesis of steroids. The total alkaloid content (0.12%) of the plants coming from Chiapas and India was the same. However, solasodine was found only in the plants of Chiapa...

  8. Distinct sesquiterpene pyridine alkaloids from in Salvadoran and Peruvian Celastraceae species.

    Science.gov (United States)

    Callies, Oliver; Núñez, Marvin J; Perestelo, Nayra R; Reyes, Carolina P; Torres-Romero, David; Jiménez, Ignacio A; Bazzocchi, Isabel L

    2017-10-01

    As part of a bioprospecting program aimed at the discovery of undescribed natural products from Salvadoran and Peruvian flora, the phytochemical investigations of four Celastraceae species, Celastrus vulcanicola, Maytenus segoviarum, Maytenus jeslkii, and Maytenus cuzcoina, were performed. The current study reports the isolation and structural characterization of five previously undescribed macrolide sesquiterpene pyridine alkaloids, named vulcanicoline-A, cuzcoinine, vulcanicoline-B, jelskiine, and vulcanicoline-C, along with sixteen known alkaloids. The structures of the alkaloids were established by spectrometric and extensive 1D and 2D NMR spectroscopic analysis, including COSY, HSQC, HMBC, and ROESY experiments. The absolute configurations of alkaloids were proposed based on optical rotation sign, and biogenetic considerations. This study represents the first phytochemical analysis of Maytenus segoviarum. Copyright © 2017 Elsevier Ltd. All rights reserved.

  9. Carry-over of pyrrolizidine alkaloids from feed to milk in dairy cows.

    Science.gov (United States)

    Hoogenboom, L A P; Mulder, P P J; Zeilmaker, M J; van den Top, H J; Remmelink, G J; Brandon, E F A; Klijnstra, M; Meijer, G A L; Schothorst, R; Van Egmond, H P

    2011-03-01

    Pyrrolizidine alkaloids are toxins present in many plants belonging to the families of Asteraceae, Boraginaceae and Fabaceae. Particularly notorious are pyrrolizidine alkaloids present in ragwort species (Senecio), which are held responsible for hepatic disease in horses and cows and may lead to the death of the affected animals. In addition, these compounds may be transferred to edible products of animal origin and as such be a threat for the health of consumers. To investigate the possible transfer of pyrrolizidine alkaloids from contaminated feed to milk, cows were put on a ration for 3 weeks with increasing amounts (50-200 g day(-1)) of dried ragwort. Milk was collected and sampled twice a day; faeces and urine twice a week. For milk, a dose-related appearance of pyrrolizidine alkaloids was found. Jacoline was the major component in milk despite being a minor component in the ragwort material. Practically no N-oxides were observed in milk, notwithstanding the fact that they constituted over 80% of the pyrrolizidine alkaloids in ragwort. The overall carry-over of the pyrrolizidine alkaloids was estimated to be only around 0.1%, but for jacoline 4%. Notwithstanding the low overall carry-over, this may be relevant for consumer health considering the genotoxic and carcinogenic properties demonstrated for some of these compounds. Analysis of the faeces and urine samples indicated that substantial metabolism of pyrrolizidine alkaloids is taking place. The toxicity and potential transfer of metabolites to milk is unknown and remains to be investigated.

  10. Australine, a pyrrolizidine alkaloid that inhibits amyloglucosidase and glycoprotein processing

    Energy Technology Data Exchange (ETDEWEB)

    Tropea, J.E.; Molyneux, R.J.; Kaushal, G.P.; Pan, Y.T.; Mitchell, M.; Elbein, A.D. (Univ. of Texas Health Science Center, San Antonio (USA))

    1989-03-07

    Australine is a polyhydroxylated pyrrolizidine alkaloid that was isolated from the seeds of the Australian tree Castanospermum australe and characterized by NMR and X-ray diffraction analysis. Since swainsonine and catanospermine are polyhydroxylated indolizidine alkaloids that inhibit specific glycosidases, the authors tested australine against a variety of exoglycosidases to determine whether it would inhibit any of these enzymes. This alkaloid proved to be a good inhibitor of the {alpha}-glucosidase amyloglucosidase (50% inhibition at 5.8 {mu}M), but it did not inhibit {beta}-glucosidase, {alpha}- or {beta}-mannosidase, or {alpha}- or {beta}-galactosidase. The inhibition of amyloglucosidase was of a competitive nature. Australine also inhibited the glycoprotein processing enzyme glucosidase I, but had only slight activity toward glucosidase II. When incubated with cultured cells, this alkaloid inhibited glycoprotein processing at the glucosidase I step and caused the accumulation of glycoproteins with Glc{sub 3}Man{sub 7-9}(GlcNAc){sub 2}-oligosaccharides.

  11. Determination of pyrrolizidine alkaloids in commercial comfrey products (Symphytum sp.).

    Science.gov (United States)

    Betz, J M; Eppley, R M; Taylor, W C; Andrzejewski, D

    1994-05-01

    The presence of hepatotoxic pyrrolizidine alkaloids in comfrey (Symphytum sp.) and the widespread use of decoctions of this plant as a beverage (herbal tea) are of increasing concern. A method for the extraction and solid-phase concentration and capillary gas chromatographic determination of these alkaloids and their N-oxides in botanical materials has been developed and was applied to eleven comfrey-containing products purchased from retail health-food outlets in the Washington, DC, area during May-June 1989. Nine of the 11 products were found to contain measurable quantities of one or more of the alkaloids, in ranges from 0.1 to 400.0 ppm. Products containing comfrey leaf in combination with one or more other ingredients were found to contain the lowest alkaloid levels. Highest levels were found in bulk comfrey root, followed by bulk comfrey leaf. The species of the bulk material was verified by thin-layer chromatography and other means.

  12. POSSIBILITY FOR APPLICATION OF LIQUEFIED GASES FOR PURIFICATION OF BARBERRY ALKALOIDS

    Directory of Open Access Journals (Sweden)

    Demyanenko D.V.

    2016-06-01

    Full Text Available Introduction. Biologically active substances (BAS of barberry roots represented by alkaloids of isoquinoline group are perspective substances for development of preparations with multiple pharmacological activities. However, now manufacture of them in Ukraine is stopped. One of the reasons of this is out-of-date production technologies of alkaloids involving use of toxic and/or flammable solvents. In the article possibility for application of liquefied gases in technology of obtaining of alkaloids from barberry roots has been studied. Materials and methods. Initial raw herb drug were barberry (Berberis vulgaris roots harvested in spring on the territory of Southern Ukraine. Their moisture content was 11%, comminuting degree was 0,5-1,4 mm. At the first stage purification of raw herb drug from lipophilic impurities (defatting was made with use of some liquefied gases: tetrafluoroethane, isobutane, difluorochloromethane and difluoromethane. Extraction of the alkaloid sum was made with difluoromethane mixed with various quantities of liquid ammonia or diethylamine as alkaline agent. Crude extracts were exposed to two-level liquefied-gas purification. At first the alkaloid bases were transformed into saline forms with aqueous solutions of acids and purified from ballast impurities with liquefied freon-22. Then alkaloid salts were reextracted from aqueous phase in the base form with liquefied mixture of difluoromethane and ammonia. Mixing of liquid phases was provided by creation of alternate gradients of temperatures and, as consequence, pressures between separators feeding alternately cool water into jacket of one of them, and warm water – into jacket of another one. Quantity of lipophilic ballast impurities and also weight of extractives were determined gravimetrically. Quantitative analysis of the alkaloid sum was made by titrimetric method after sedimentation of alkaloids with volumetric solution of phosphomolybdic acid. Results and discussion

  13. Analogue MIMO Detection

    Directory of Open Access Journals (Sweden)

    McNamara Darren

    2006-01-01

    Full Text Available In this contribution we propose an analogue receiver that can perform turbo detection in MIMO systems. We present the case for a receiver that is built from nonlinear analogue devices, which perform detection in a "free-flow" network (no notion of iterations. This contribution can be viewed as an extension of analogue turbo decoder concepts to include MIMO detection. These first analogue implementations report reductions of few orders of magnitude in the number of required transistors and in consumed energy, and the same order of improvement in processing speed. It is anticipated that such analogue MIMO decoder could bring about the same advantages, when compared to traditional digital implementations.

  14. Drug development against tuberculosis: Impact of alkaloids.

    Science.gov (United States)

    Mishra, Shardendu K; Tripathi, Garima; Kishore, Navneet; Singh, Rakesh K; Singh, Archana; Tiwari, Vinod K

    2017-09-08

    Despite of the advances made in the treatment and management, tuberculosis (TB) still remains one of main public health problem. The contrary effects of first and second-line anti-tuberculosis drugs have generated extended research interest in natural products in the hope of devising new antitubercular leads. Interestingly, plethoras of natural products have been discovered to exhibit activity towards various resistant strains of M. tuberculosis. Extensive applications of alkaloids in the field of therapeutics is well-established and nowday's researches being pursued to develop new potent drugs from natural sources for tuberculosis. Alkaloids are categorized in quite a few groups according to their structures and isolation from both terrestrial and marine sources. These new drugs might be a watershed in the battle against tuberculosis. This review summarizes alkaloids, which were found active against Mycobacteria since last ten years with special attention on the study of structure-activity relationship (SAR) and mode of action with their impact in drug discovery and development against tuberculosis. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  15. ALKALOIDS OF SOME EUROPEAN AND MACARONESIAN SEDOIDEAE AND SEMPERVIVOIDEAE (CRASSULACEAE)

    NARCIS (Netherlands)

    STEVENS, JF; THART, H; HENDRIKS, H; MALINGRE, TM

    1992-01-01

    Some 22 pyrrolidine and piperdine alkaloids were detected in the leafy parts of Sedum acre, S. aetnense, S. anglicum, S. brissemoreti, S. farinosum, S. fusiforme, S. lancerottense, S. melanantherum, and S. nudum. In addition to the alkaloids known from S. acre, 1-(2-pyrrolidyl)-propan-2-one and

  16. Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance

    Energy Technology Data Exchange (ETDEWEB)

    Rosas, Lisandra V.; Veiga, Thiago Andre M.; Fernandes, Joao B.; Vieira, Paulo C.; Silva, M. Fatima das G.F. da, E-mail: dmfs@power.ufscar.b [Universidade Federal de Sao Carlos (DQ/UFSCar), SP (Brazil). Dept. de Quimica

    2011-07-01

    The dichloromethane extract from the stems of Raputia praetermissa afforded four new compounds, 4-deoxyraputindole C (1), raputimonoindole A-B (2, 3), and hexadecanyl 2-hydroxy- 4-methoxy-cinnamate (5), besides the alkaloids 5-(4-methoxymethylfuran-2-yl)-1H-indole (raputimonoindole C), furoquinolines maculosidine, robustine, evolitrine and dictamnine. The hexane extract yielded N-methyl-4-methoxyquinoline-2(1H)-one, skimmianine, cycloartenone, sitosterol, stigmasterol and sitostenone. The anthranilate alkaloid content indicates that the genus is strongly related to those included in Cusparieae tribe, but differs from Neoraputia by the absence of prenylindole alkaloids in the late, whose species have previously been placed in Raputia. (author)

  17. Aptamer-Based Molecular Recognition of Lysergamine, Metergoline and Small Ergot Alkaloids

    Directory of Open Access Journals (Sweden)

    Johan Robbens

    2012-12-01

    Full Text Available Ergot alkaloids are mycotoxins produced by fungi of the genus Claviceps, which infect cereal crops and grasses. The uptake of ergot alkaloid contaminated cereal products can be lethal to humans and animals. For food safety assessment, analytical techniques are currently used to determine the presence of ergot alkaloids in food and feed samples. However, the number of samples which can be analyzed is limited, due to the cost of the equipment and the need for skilled personnel. In order to compensate for the lack of rapid tests for the detection of ergot alkaloids, the aim of this study was to develop a specific recognition element for ergot alkaloids, which could be further applied to produce a colorimetric reaction in the presence of these toxins. As recognition elements, single-stranded DNA ligands were selected by using an iterative selection procedure named SELEX, i.e., Systematic Evolution of Ligands by EXponential enrichment. After several selection cycles, the resulting aptamers were cloned and sequenced. A surface plasmon resonance analysis enabled determination of the dissociation constants of the complexes of aptamers and lysergamine. Dissociation constants in the nanomolar range were obtained with three selected aptamers. One of the selected aptamers, having a dissociation constant of 44 nM, was linked to gold nanoparticles and it was possible to produce a colorimetric reaction in the presence of lysergamine. This system could also be applied to small ergot alkaloids in an ergot contaminated flour sample.

  18. Scientific investigation of crude alkaloids from medicinal plants for the management of pain.

    Science.gov (United States)

    Shoaib, Mohammad; Shah, Syed Wadood Ali; Ali, Niaz; Shah, Ismail; Ullah, Shafi; Ghias, Mehreen; Tahir, Muhammad Nawaz; Gul, Farah; Akhtar, Sohail; Ullah, Abd; Akbar, Wajid; Ullah, Asad

    2016-06-13

    Tissue damage is associated with pain, which is an alarming sign. Aspirin and morphine have been widely used in recent decades for management of pain. Medicinal herbs have been in use for treatment of different diseases for centuries. Many of these herbs possess analgesic activity with relatively less incidences of adverse effects. The strong positive correlation of alkaloids in medicinal plants for analgesic activity persuades an intention to determine possible analgesic activity of total alkaloids extracted from the selected medicinal plants using animal models to answer its possible mechanisms. Crude alkaloids from selected medicinal plants (Woodfordia fruticosa, Adhatoda vasica, Chenopodium ambrosioides, Vitex negundo, Peganum harmala and Broussonetia papyrifera) were extracted as per reported literature. The test crude alkaloids were screened foracute toxicity study. Writhings induced by acetic acid, tail immersion method and formalin-induced nociception assay procedures were used for possible analgesic effects of the crude alkaloids. Crude alkaloids were safe up to dose of 1250 mg/kg body weight in mice. The alkaloids significantly reduced the abdominal constrictions, and increased the time for paw licking response in both phases with a significant raise in latency time in nociception models (P ≤ 0.05). Moreover, the antinociceptive response was significantly attenuated by pretreatment with naloxone suggesting involvement of the opioid receptors for possible antinociceptive action. Crude alkaloids of Woodfordia fruticosa and Peganum harmala showed prominent analgesic potentials through inhibition of peripheral as well as central nervous system mechanisms. Further work is required for isolation of the pharmacologically active constituents.

  19. Antiprotozoal alkaloids from Psychotria prunifolia (Kunth) Steyerm

    International Nuclear Information System (INIS)

    Kato, Lucilia; Oliveira, Cecilia M.A. de; Faria, Emiret O.; Ribeiro, Laryssa C.; Carvalho, Brenda G.; Silva, Cleuza C. da; Santin, Silvana M.O.; Schuque, Ivania T.A.; Nakamura, Celso V.; Britta, Elisandra A.; Miranda, Nathielle; Iglesias, Amadeu H.; Delprete, Piero G.

    2012-01-01

    The continuity of the phyto chemical study of crude extracts of P. prunifolia's roots and branches led to the isolation of five indole-β-carboline alkaloids. Among them, the 10-hydroxy-iso-deppeaninol and N-oxide-10-hydroxy-antirhine derivatives are described here for the first time. The structures were achieved through 1D and 2D NMR, IR and HRMS analyses. The branches and roots crude extracts and the alkaloids 14-oxoprunifoleine and strictosamide showed selective activity against L. amazonensis, with IC 50 values of 16.0 and 40.7 μg per mL, respectively. (author)

  20. Cinchona alkaloids in asymmetric organocatalysis

    NARCIS (Netherlands)

    Marcelli, T.; Hiemstra, H.

    2010-01-01

    This article reviews the applications of cinchona alkaloids as asymmetric catalysts. In the last few years, characterized by the resurgence of interest in asymmetric organocatalysis, cinchona derivatives have been shown to catalyze an outstanding array of chemical reactions, often with remarkable

  1. Pyrrolizidine alkaloids from Heliotropium megalanthum.

    Science.gov (United States)

    Reina, M; Gonzalez-Coloma, A; Gutierrez, C; Cabrera, R; Henriquez, J; Villarroel, L

    1998-11-01

    Two pyrrolizidine alkaloids, megalanthonine (1) and lycopsamine (2), have been isolated from Heliotropium megalanthum. The structure of the novel compound 1 was determined by spectroscopic methods. The insecticidal, antifeedant, and antifungal effects of compounds 1 and 2 have been evaluated.

  2. [Relativity among starch quantity, polysaccharides content and total alkaloid content of Dendrobium loddigesii].

    Science.gov (United States)

    Zhu, Hua; Teng, Jianbei; Cai, Yi; Liang, Jie; Zhu, Yilin; Wei, Tao

    2011-12-01

    To find out the relativity among starch quantity, polysaccharides content and total alkaloid content of Dendrobium loddigesii. Microscopy-counting process was applied to starch quantity statistics, sulfuric acid-anthrone colorimetry was used to assay polysaccharides content and bromocresol green colorimetry was used to assay alkaloid content. Pearson product moment correlation analysis, Kendall's rank correlation analysis and Spearman's concordance coefficient analysis were applied to study their relativity. Extremely significant positive correlation was found between starch quantity and polysaccharides content, and significant negative correlation between alkaloid content and starch quantity was discovered, as well was between alkaloid content and polysaccharides content.

  3. Pyrrole alkaloids from the fruits of Morus alba.

    Science.gov (United States)

    Kim, Seon Beom; Chang, Bo Yoon; Hwang, Bang Yeon; Kim, Sung Yeon; Lee, Mi Kyeong

    2014-12-15

    Phytochemical investigation of the fruits of Morus alba afforded seventeen pyrrole alkaloids including five new compounds. The structures of five new pyrrole alkaloids, named morroles B-F (4, 5, 7, 16 and 17), were determined on the basis of spectroscopic interpretations. 4-[Formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]butanoate (2) was synthesized by chemical reaction but first isolated from nature. Among isolated compounds, compounds 6 and 14 significantly inhibited pancreatic lipase activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

  4. Biological activity of the alkaloids of Erythroxylum coca and Erythroxylum novogranatense

    NARCIS (Netherlands)

    Salemink, C.A.; Novák, M.; Khan, I.

    1984-01-01

    The cultivated Erythroxylum varieties E. coca var. coca, E. coca var. ipadu, E. novogranatense var. novogranatense and E. novogranatense var. truxillense contain 18 alkaloids, identified so far, belonging to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid. The biological

  5. Protein and alkaloid patterns of the floral nectar in some solanaceous species.

    Science.gov (United States)

    Kerchner, András; Darók, Judit; Bacskay, Ivett; Felinger, Attila; Jakab, Gábor; Farkas, Ágnes

    2015-09-01

    The family Solanaceae includes several melliferous plants, which tend to produce copious amounts of nectar. Floral nectar is a chemically complex aqueous solution, dominated by sugars, but minor components such as amino acids, proteins, flavonoids and alkaloids are present as well. This study aimed at analysing the protein and alkaloid profile of the nectar in seven solanaceous species. Proteins were examined with SDS-PAGE and alkaloids were analyzed with HPLC. The investigation of protein profile revealed significant differences in nectar-protein patterns not only between different plant genera, but also between the three Nicotiana species investigated. SDS-PAGE suggested the presence of several Nectarin proteins with antimicrobial activity in Nicotiana species. The nectar of all tobacco species contained the alkaloid nicotine, N. tabacum having the highest nicotine content. The nectar of Brugmansia suaveolens, Datura stramonium, Hyoscyamus niger and Lycium barbarum contained scopolamine, the highest content of which was measured in B. suaveolens. The alkaloid concentrations in the nectars of most solanaceous species investigated can cause deterrence in honeybees, and the nectar of N. rustica and N. tabacum can be considered toxic for honeybees.

  6. [Effects of Total Alkaloids of Harmaline on Learning and Memory in Vascular Dementia Rats].

    Science.gov (United States)

    Zhang, Xiao-shuang; Sun, Jian-ning; Yu, Hui-ling

    2015-11-01

    To investigate the effects of total alkaloids of harmaline on learning and memory in vascular dementia rats, and its mechanism. The model rats of vascular dementia were established with bilateral carotid artery ligation. After 30 days, the model rats were randomly divided into six groups: sham group, model group, nicergoline tablets 7 mg/kg group, and 25, 12.5 and 6.25 mg/kg dose groups of total alkaloids of harmaline, the rats were given medicine for 30 days. Learning and memory abilities were tested by Morris water maze, histomorphology in hippocampal CA1 area were observed by HE staining, BAX and BCL-2 protein expression in hippocampal CA1 area were detected by immunohistochemistry. Compared with model group, 25 mg/kg group of total alkaloids of harmaline shortened the incubation period in the third and fourth day significantly, 12.5 mg/kg group of total alkaloids of harmaline shortened the incubation period in the fourth day. 25 and 12.5 mg/kg groups of total alkaloids of harmaline significantly increased the times crossing the target. Total alkaloids of harmaline improved the neurons pathological changes of rat in the hippocampus CA1 area, 25 and 12.5 mg/kg of total alkaloids of harmaline downregulated the expression of apoptosis proteins BAX, upregulated the protein expression of BCL-2. Total alkaloids of harmaline can improve the learning and memory abilities in vascular dementia rats, which probably is related to inhibiting apoptosis of hippocampus cell.

  7. Changes in plant defense chemistry (pyrrolizidine alkaloids) revealed through high-resolution spectroscopy

    Science.gov (United States)

    Carvalho, Sabrina; Macel, Mirka; Schlerf, Martin; Moghaddam, Fatemeh Eghbali; Mulder, Patrick P. J.; Skidmore, Andrew K.; van der Putten, Wim H.

    2013-06-01

    Plant toxic biochemicals play an important role in defense against natural enemies and often are toxic to humans and livestock. Hyperspectral reflectance is an established method for primary chemical detection and could be further used to determine plant toxicity in the field. In order to make a first step for pyrrolizidine alkaloids detection (toxic defense compound against mammals and many insects) we studied how such spectral data can estimate plant defense chemistry under controlled conditions. In a greenhouse, we grew three related plant species that defend against generalist herbivores through pyrrolizidine alkaloids: Jacobaea vulgaris, Jacobaea erucifolia and Senecio inaequidens, and analyzed the relation between spectral measurements and chemical concentrations using multivariate statistics. Nutrient addition enhanced tertiary-amine pyrrolizidine alkaloids contents of J. vulgaris and J. erucifolia and decreased N-oxide contents in S. inaequidens and J. vulgaris. Pyrrolizidine alkaloids could be predicted with a moderate accuracy. Pyrrolizidine alkaloid forms tertiary-amines and epoxides were predicted with 63% and 56% of the variation explained, respectively. The most relevant spectral regions selected for prediction were associated with electron transitions and Csbnd H, Osbnd H, and Nsbnd H bonds in the 1530 and 2100 nm regions. Given the relatively low concentration in pyrrolizidine alkaloids concentration (in the order of mg g-1) and resultant predictions, it is promising that pyrrolizidine alkaloids interact with incident light. Further studies should be considered to determine if such a non-destructive method may predict changes in PA concentration in relation to plant natural enemies. Spectroscopy may be used to study plant defenses in intact plant tissues, and may provide managers of toxic plants, food industry and multitrophic-interaction researchers with faster and larger monitoring possibilities.

  8. Interactions between β-carboline alkaloids and bovine serum albumin: Investigation by spectroscopic approach

    International Nuclear Information System (INIS)

    Nafisi, Shohreh; Panahyab, Ataollah; Bagheri Sadeghi, Golshan

    2012-01-01

    β-Carboline alkaloids are present in medicinal plants such as Peganum harmala L. that have been used as folk medicine in anticancer therapy. BSA is the major soluble protein constituent of the circulatory system, and has many physiological functions including the transport of a variety of compounds. This study is the first attempt to investigate the binding of β-carboline alkaloids to BSA by using a constant protein concentration and varying drug concentrations at pH 7.2. FTIR and UV–Vis spectroscopic methods were used to analyze the binding modes of β-carboline alkaloids, the binding constants and the effects of drug complexation on BSA stability and conformation. Spectroscopic evidence showed that β-carboline alkaloids bind BSA via hydrophobic interaction and van der Waals contacts along with H-bonding with the –NH groups, with overall binding constants of K harmine–BSA =2.04×10 4 M −1 , K tryptoline–BSA =1.2×10 4 M −1 , K harmaline–BSA =5.04×10 3 M −1 , K harmane–BSA =1.41×10 3 M −1 and K harmalol–BSA =1.01×10 3 M −1 , assuming that there is one drug molecule per protein. The BSA secondary structure was altered with a major decrease of α-helix from 64% (free protein) to 59% (BSA–harmane), 56% (BSA–harmaline and BSA–harmine), 55% (BSA–tryptoline), 54% (BSA–harmalol) and β-sheet from 15% (free protein) to 6–8% upon β-carboline alkaloids complexation, inducing a partial protein destabilization. - Highlights: ► We model the binding of β-carboline alkaloids to BSA by using the spectroscopic methods. ► We investigate the effects of drug complexation on BSA stability and conformation. ► A partial protein destabilization occurred at high alkaloids concentration. ► Alkaloids bind BSA via hydrophobic interactions and H-bonding with the ---NH groups. ► BSA can be considered as a good carrier for transportation of β-carboline alkaloids.

  9. Analysis of Alkaloids from Physalis peruviana by Capillary GC, Capillary GC-MS, and GC-FTIR.

    Science.gov (United States)

    Kubwabo, C; Rollmann, B; Tilquin, B

    1993-04-01

    The alkaloid composition of the aerial parts and roots of PHYSALIS PERUVIANA was analysed by capillary GC (GC (2)), GC (2)-MS and GC (2)-FTIR. Eight alkaloids were identified, three of those alkaloids are 3beta-acetoxytropane and two N-methylpyrrolidinylhygrine isomers, which were not previously found in the genus PHYSALIS. A reproduction of the identification of alkaloids detected in the plant by the use of retention indices has been proposed.

  10. How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production.

    Science.gov (United States)

    Marconi, Patricia L; Alvarez, María A; Pitta-Alvarez, Sandra I

    2007-01-01

    Hairy roots of Brugmansia candida produce the tropane alkaloids scopolamine and hyoscyamine. In an attempt to divert the carbon flux from competing pathways and thus enhance productivity, the polyamine biosynthesis inhibitors cyclohexylamine (CHA) and methylglyoxal-bis-guanylhydrazone (MGBG) and the phenylalanine-ammonia-lyase inhibitor cinnamic acid were used. CHA decreased the specific productivity of both alkaloids but increased significantly the release of scopolamine (approx 500%) when it was added in the mid-exponential phase. However, when CHA was added for only 48 h during the exponential phase, the specific productivity of both alkaloids increased (approx 200%), favoring scopolamine. Treatment with MGBG was detrimental to growth but promoted release into the medium of both alkaloids. However, when it was added for 48 h during the exponential phase, MGBG increased the specific productivity (approx 200%) and release (250- 1800%) of both alkaloids. Cinnamic acid alone also favored release but not specific productivity. When a combination of CHA or MGBG with cinnamic acid was used, the results obtained were approximately the same as with each polyamine biosynthesis inhibitor alone, although to a lesser extent. Regarding root morphology, CHA inhibited growth of primary roots and ramification. However, it had a positive effect on elongation of lateral roots.

  11. Retina-Inspired Filter.

    Science.gov (United States)

    Doutsi, Effrosyni; Fillatre, Lionel; Antonini, Marc; Gaulmin, Julien

    2018-07-01

    This paper introduces a novel filter, which is inspired by the human retina. The human retina consists of three different layers: the Outer Plexiform Layer (OPL), the inner plexiform layer, and the ganglionic layer. Our inspiration is the linear transform which takes place in the OPL and has been mathematically described by the neuroscientific model "virtual retina." This model is the cornerstone to derive the non-separable spatio-temporal OPL retina-inspired filter, briefly renamed retina-inspired filter, studied in this paper. This filter is connected to the dynamic behavior of the retina, which enables the retina to increase the sharpness of the visual stimulus during filtering before its transmission to the brain. We establish that this retina-inspired transform forms a group of spatio-temporal Weighted Difference of Gaussian (WDoG) filters when it is applied to a still image visible for a given time. We analyze the spatial frequency bandwidth of the retina-inspired filter with respect to time. It is shown that the WDoG spectrum varies from a lowpass filter to a bandpass filter. Therefore, while time increases, the retina-inspired filter enables to extract different kinds of information from the input image. Finally, we discuss the benefits of using the retina-inspired filter in image processing applications such as edge detection and compression.

  12. Isolation, biosynthesis and biological activity of alkaloids of Tylophora asthmatica, a versatile medicinal plant

    International Nuclear Information System (INIS)

    Mulchandani, N.B.

    1987-01-01

    Tylophorine and related new alkaloids have been isolated from Tylophora asthmatics, Pergularia pallida and Ficus hispida plants. Biosynthesis of this group of alkaloids has been carried out using various labelled precursors for the first time and from the systematic degradation of the isolated radiolabelled tylophorine, it has been concluded that these alkaloids arise from one molecule each of tyrosine, phenylalanine and ornithine. The interactions of Tylophora alkaloids particularly tylophorinidine with biomolecules such as lysozyme and bovine serum albumin have also been studied and binding characteristics determined. It was found that Tylophora alkaloid extract possesses antianaphylactic activity as observed in passive peritoneal anaphylaxis in rats. The drug also possessed mild antihistaminic and anticholinergic activities. Studies of the extract on the bronchial smooth muscle both in vivo and in vitro did not reveal bronchiodilator potential of the drug. In addition, the distribution and metabolism of the drug was studied in vivo using 14 C radiolabelled alkaloids prepared by biosynthetic method. This study further revealed its usefulness since the drug is absorbed by vital organs and also it is not metabolised into fragments which could cause some other damage. Tylophora alkaloids have also been found to be anti-mutagenic. 10 tables, 5 figures, 24 refs. (author)

  13. Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr

    Energy Technology Data Exchange (ETDEWEB)

    Santos, Djalma A.P. dos; Vieira, Paulo C; Silva, M. Fatima das G.F. da; Fernandes, Joao B [Universidade Federal de Sao Carlos, SP (Brazil). Dept. de Quimica; Rattray, Lauren; Croft, Simon L [London School of Hygiene and Tropical Medicine, London (United Kingdom). Dept. of Infectious and Tropical Diseases

    2009-07-01

    Eleven acridone alkaloids isolated from Swinglea glutinosa (Bl.) Merr. were examined for in vitro activity against chloroquine-sensitive Plasmodium falciparum 3D7, Trypanosoma brucei rhodesiense STIB900 and Leishmania donovani L82. An assay with KB cells was developed in order to compare in vitro toxicity of alkaloids with the selective action on the parasites. Nine of the compounds had IC{sub 50} values ranging from 0.3 to 11.6 {mu}M against P. falciparum. In contrast, a small number of compounds showed significant activity against T. brucei rhodesiense and none had activity against L. donovani. Among the alkaloids three had IC{sub 50} < 1.0 {mu}M against P. falciparum, whereas against T. b. rhodesiense five had IC{sub 50} < 10 {mu}M. The characterization of the acridone alkaloids, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9 (10H)-one (1), 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methylfuro [3,2-b] acridin-5(10H)-one (2) and 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[ 2,3-a]acridin-12(7H)-one (3), is discussed, as well as the structure-activity relationship of all compounds assayed. Isolation and spectral data of alkaloids 1-3 are described for the first time although their cytotoxicities to cancer cells have been described before. (author)

  14. Ornithine decarboxylase, polyamines, and pyrrolizidine alkaloids in senecio and crotalaria.

    Science.gov (United States)

    Birecka, H; Birecki, M; Cohen, E J; Bitonti, A J; McCann, P P

    1988-01-01

    When tested for ornithine and arginine decarboxylases, pyrrolizidine alkaloid-bearing Senecio riddellii, S. longilobus (Compositae), and Crotalaria retusa (Leguminosae) plants exhibited only ornithine decarboxylase activity. This contrasts with previous studies of four species of pyrrolizidine alkaloid-bearing Heliotropium (Boraginaceae) in which arginine decarboxylase activity was very high relative to that of ornithine decarboxylase. Unlike Heliotropium angiospermum and Heliotropium indicum, in which endogenous arginine was the only detectable precursor of putrescine channeled into pyrrolizidines, in the species studied here-using difluoromethylornithine and difluoromethylarginine as the enzyme inhibitors-endogenous ornithine was the main if not the only precursor of putrescine converted into the alkaloid aminoalcohol moiety. In S. riddellii and C. retusa at flowering, ornithine decarboxylase activity was present mainly in leaves, especially the young ones. However, other very young organs such as inflorescence and growing roots exhibited much lower or very low activities; the enzyme activity in stems was negligible. There was no correlation between the enzyme activity and polyamine or alkaloid content in either species. In both species only free polyamines were detected except for C. retusa roots and inflorescence-with relatively very high levels of these compounds-in which conjugated putrescine, spermidine, and spermine were also found; agmatine was not identified by HPLC in any plant organ except for C. retusa roots with rhizobial nodules. Organ- or age-dependent differences in the polyamine levels were small or insignificant. The highest alkaloid contents were found in young leaves and inflorescence.

  15. Biosistematik species Annona muricata Annona squamosa dan Annona reticulata dengan pendekatan alkaloid

    Directory of Open Access Journals (Sweden)

    Hamidah Hamidah

    2013-03-01

    Full Text Available This research aimed to explore kinship Annona muricata, Annona squamosa and Annona reticulata on the basis alkaloid content. Study phenotype Annona muricata, Annona squamosa and Annona reticulata based alkaloid content. Data alkaloid obtained are thenprocessed by a computer program SPSS version 14. The results of this study indicate that the presence of variations in the characterof the three types of Annona of species alkaloid. From the data analysis it can be seen that there are differences in the variations that occur in Annona muricata, Annona squamosa and Annona reticulata by different habitats and is a variation of phenotypic variation.Dendrogram grouping results suggest that Annona squamosa and Annona reticulata fenetic ties closer, so clumped into one large group while Annona muricata split away from the other groups.

  16. Indole alkaloids and other constituents of Rauwolfia serpentina.

    Science.gov (United States)

    Itoh, Atsuko; Kumashiro, Tomoko; Yamaguchi, Machiko; Nagakura, Naotaka; Mizushina, Yoshiyuki; Nishi, Toyoyuki; Tanahashi, Takao

    2005-06-01

    From the dried roots of Rauwolfia serpentina were isolated five new indole alkaloids, N(b)-methylajmaline (1), N(b)-methylisoajmaline (2), 3-hydroxysarpagine (3), yohimbinic acid (4), isorauhimbinic acid (5), a new iridoid glucoside, 7-epiloganin (6), and a new sucrose derivative, 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (7), together with 20 known compounds. The structures of the new compounds were determined by spectroscopic and chemical means. The inhibitory activities of the selected alkaloids on topoisomerase I and II and their cytotoxicity against the human promyelocytic leukemia (HL-60) cell lines were assessed.

  17. Effects of antibacterial agents on in vitro ovine ruminal biotransformation of the hepatotoxic pyrrolizidine alkaloid jacobine.

    OpenAIRE

    Wachenheim, D E; Blythe, L L; Craig, A M

    1992-01-01

    Ingestion of pyrrolizidine alkaloids, naturally occurring plant toxins, causes illness and death in a number of animal species. Senecio jacobaea pyrrolizidine alkaloids cause significant economic losses due to livestock poisoning, particularly in the Pacific Northwest. Some sheep are resistant to pyrrolizidine alkaloid poisoning, because ovine ruminal biotransformation detoxifies free pyrrolizidine alkaloids in digesta. Antibacterial agents modify ruminal fermentation. Pretreatment with antib...

  18. OVIPOSITION AND OVICIDAL ACTIVITIES OF ALKALOIDAL ...

    African Journals Online (AJOL)

    1000 ppm concentration and ovicidal activity at 25-100 ppm concentration against Culex quinquefasciatus and Culex tritaeniorhynchus. Water treated with alkaloidal extract at 1000ppm received significantly more egg rafts of vector mosquitoes ...

  19. Crystal structure of indoline alkaloids kopsinilam, kopsinine, and the salts of the latter

    DEFF Research Database (Denmark)

    Adizov, Sh. M.; Tashkhodzhaev, B.; Kunafiev, R. Zh.

    2016-01-01

    N1 in the bases and the salts. Tetrahedral hybridization of the atom N1 in indoline alkaloids favors the formation of their double salts, what is unlikely for indole and indolinine alkaloids. In the halogen double salts there is an intramolecular Н bond between one of the protons of the NH2 group......Indoline alkaloids kopsinilam and kopsinine extracted from the plant Vinca erecta have been studied by X-ray crystallography; mono and double salts of the latter alkaloid also have been examined. Experimentally determined positions of Н atoms suggest sp3 hybridization of the indoline nitrogen atom...... and the oxygen of the methoxycarbonyl group, that is absent in the mono salts and pure bases....

  20. Alternative extraction of alkaloid anticarcinogens from Brazilian "vinca rosea" using Ion exchange chromatography

    Directory of Open Access Journals (Sweden)

    Sérgio Freire de Carvalhaes

    Full Text Available Extracts in ethanol and ethanol-ammonia of dried leaves from Catharanthus roseus, gathered at Rio de Janeiro state, were adsorbed in a strongly acidic cation exchange resin with sulfonic acid group, using the finite bath method, resulting in an alkaloid retained fraction and an acidic and neutral unretained fraction. High Performance Liquid Chromatography showed the isolation of the alkaloid fraction to be highly selective and with good performance, with an absence of alkaloids in the unretained fraction, while the retained fraction presented 1,54-6,35 mg/g of vindoline and 0,12-0,91 mg/g of vinblastine, common for an alkaloid-rich concentrate, usually obtained by classic extraction with several steps using solvents.

  1. Alkaloid-Containing Plants Poisonous to Cattle and Horses in Europe.

    Science.gov (United States)

    Cortinovis, Cristina; Caloni, Francesca

    2015-12-08

    Alkaloids, nitrogen-containing secondary plant metabolites, are of major interest to veterinary toxicology because of their occurrence in plant species commonly involved in animal poisoning. Based on epidemiological data, the poisoning of cattle and horses by alkaloid-containing plants is a relatively common occurrence in Europe. Poisoning may occur when the plants contaminate hay or silage or when forage alternatives are unavailable. Cattle and horses are particularly at risk of poisoning by Colchicum autumnale (meadow saffron), Conium maculatum (poison hemlock), Datura stramonium (jimson weed), Equisetum palustre (marsh horsetail), Senecio spp. (ragwort and groundsel) and Taxus baccata (European yew). This review of poisonous alkaloid-containing plants describes the distribution of these plants, conditions under which poisoning occurs, active toxic principles involved and subsequent clinical signs observed.

  2. A new alkaloid from the fruit of Nandina domestica Thunb.

    Science.gov (United States)

    Peng, Cai-Ying; Liu, Jian-Qun; Zhang, Rui; Shu, Ji-Cheng

    2014-01-01

    A new steroidal alkaloid, (20S,22R,24R)-24-ethyl-3-oxocholest-4-en-22-amino, named as nandsterine (1), together with 10 known alkaloids, palmatine (2), O-methylbulbocapnine (3), nantenine (4), dehydronantenine (5), glaucine (6), didehydroglaucine (7), dehydrocorydaline (8), jatrorrhizine (9), magnoflorine (10) and berberine (11), was isolated from the fruit of Nandina domestica Thunb. Their structures were elucidated by using spectroscopic methods as well as by comparing with the published data. Compound 1 was a new class of steroidal alkaloid isolated from the family Berberidaceae, meanwhile compounds 2, 3, 6-8 and 10 were obtained from N. domestica for the first time. Compound 1 exhibited cytotoxicity against HL-60 cells (human leukaemia) with IC50 values of 52.1 μM.

  3. [Effect of different parts, harvesting time and processing technologies on alkaloids content of Coptis chinensis adventitious root].

    Science.gov (United States)

    Pang, Jie; Wang, De-Zhen; Zou, Zong-Yao; Wang, Yan-Zhi; Gao, Qian; Li, Xue-Gang

    2014-03-01

    To investigate the effect of different parts, harvesting time and processing technologies on alkaloids content of Coptis chinensis adventitious root. The content of alkaloids were analyzed by HPLC. The content of total alkaloids in adventitious root harvested in different time was ranged from 2.5% to 2.9%, in which that of berberine and coptisine were the highest, reaching to 1%, and that of palmatine was only 0.1%. It suggested there was no significant difference of total alkaloids at different harvesting time. Nevertheless, the difference of the alkaloids content from different parts was much significant. The content of total alkaloid of adventitious root near to rhizome was about 4%, 2 times higher than that away from rhizome (only 2%). In addition, different processing technologies would affect alkaloids content obviously. There was hardly loss of alkaloids when the fresh adventitious root was washed with water, but it would decrease alkaloids content when the dried adventitious root was washed. Medicine value of Coptis chinensis adventitious root near to rhizome is higher than that away from rhizome. And fresh Coptis chinensis adventitious root can be washed with water.

  4. Maneuvering control and configuration adaptation of a biologically inspired morphing aircraft

    Science.gov (United States)

    Abdulrahim, Mujahid

    Natural flight as a source of inspiration for aircraft design was prominent with early aircraft but became marginalized as aircraft became larger and faster. With recent interest in small unmanned air vehicles, biological inspiration is a possible technology to enhance mission performance of aircraft that are dimensionally similar to gliding birds. Serial wing joints, loosely modeling the avian skeletal structure, are used in the current study to allow significant reconfiguration of the wing shape. The wings are reconfigured to optimize aerodynamic performance and maneuvering metrics related to specific mission tasks. Wing shapes for each mission are determined and related to the seagulls, falcons, albatrosses, and non-migratory African swallows on which the aircraft are based. Variable wing geometry changes the vehicle dynamics, affording versatility in flight behavior but also requiring appropriate compensation to maintain stability and controllability. Time-varying compensation is in the form of a baseline controller which adapts to both the variable vehicle dynamics and to the changing mission requirements. Wing shape is adapted in flight to minimize a cost function which represents energy, temporal, and spatial efficiency. An optimal control architecture unifies the control and adaptation tasks.

  5. Molekulare Identifizierung und Charakterisierung der Flavin-abhängigen Monooxygenasen in verschiedenen Pyrrolizidin-Alkaloid-adaptierten Insekten

    OpenAIRE

    Wang, Linzhu

    2013-01-01

    Several insect lineages have developed diverse strategies to sequester toxic pyrrolizidine alkaloids from food-plants for their own defense. Here, we show that in two highly divergent insect taxa, the hemimetabolous grasshoppers and the holometabolous butterflies, an almost identical strategy evolved independently for safe accumulation of pyrrolizidine alkaloids. This strategy involves a pyrrolizidine alkaloid N-oxygenase that transfers the pyrrolizidine alkaloids to their respect...

  6. Lycopodium alkaloids from Palhinhaea cernua

    Energy Technology Data Exchange (ETDEWEB)

    Zhao, Fu-Wei [Graduate University of Chinese Academy of Sciences, Beijing (China); Luo, Ji-Feng; Wang, Yue-Hu, E-mail: wangyuehu@mail.kib.ac.cn [Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences (China); Sun, Qian-Yun; Yang, Fu-Mei [Key Laboratory of Chemistry for Natural Products, Guizhou Province and Chinese Academy of Sciences (China); Liu, Fang [College of Landscape and Horticulture, Yunnan Agricultural University (China); Long, Chun-Lin, E-mail: long@mail.kib.ac.cn [College of Life and Environmental Sciences, Minzu University of China, Beijing, (China)

    2012-07-01

    Two new Lycopodium alkaloids, acetyllycoposerramine M and palcernine A were isolated from whole plant extracts of Palhinhaea cernua L. together with ten previously identified compounds. The structures of the new compounds were elucidated by spectroscopic methods and single-crystal X-ray diffraction analyses using the Flack parameter. (author)

  7. Alkaloids and acetogenins in Annonaceae development: biological considerations

    Directory of Open Access Journals (Sweden)

    Alma Rosa González-Esquinca

    2014-01-01

    Full Text Available Chemical studies of the plant family Annonaceae have intensified in the last several decades due to the discovery of annonaceous molecules with medicinal potential (e.g., benzylisoquinoline alkaloids and acetogenins. Approximately 500 alkaloids have been identified in 138 Annonaceae species in 43 genera. In addition, until 2004, 593 annonaceous acetogenins (ACGs had been identified, from 51 species in 13 genera.This suggests that plants from this family allocate important resources to the biosynthesis of these compounds. Despite the diversity of these molecules, their biological roles, including their physiological and/or ecological functions, are not well understood. In this study, it was provided new data describing the variety and distribution of certain alkaloids and ACGs in annonaceous plants in distinct stages of development. The potential relationships among some of these compounds and the seasonally climatic changes occurring in the plant habitat are also discussed. These data will improve our understanding of the secondary metabolism of these pharmacologically important molecules and their expression patterns during development, which will help to determine the optimal growth conditions and harvest times for their production.

  8. Effects of the anti-malarial compound cryptolepine and its analogues in human lymphocytes and sperm in the Comet assay.

    Science.gov (United States)

    Gopalan, Rajendran C; Emerce, Esra; Wright, Colin W; Karahalil, Bensu; Karakaya, Ali E; Anderson, Diana

    2011-12-15

    Malaria is a mosquito-borne infectious disease caused by the genus Plasmodium. It causes one million deaths per year in African children under the age of 5 years. There is an increasing development of resistance of malarial parasites to chloroquine and other currently used anti-malarial drugs. Some plant products such as the indoloquinoline alkaloid cryptolepine have been shown to have potent activity against P. falciparum in vitro. On account of its toxicity, cryptolepine is not suitable for use as an antimalarial drug but a number of analogues of cryptolepine have been synthesised in an attempt to find compounds that have reduced cytotoxicity and these have been investigated in the present study in human sperm and lymphocytes using the Comet assay. The results suggest that cryptolepine and the analogues cause DNA damage in lymphocytes, but appear to have no effect on human sperm at the assessed doses. In the context of antimalarial drug development, the data suggest that all cryptolepine compounds and in particular 2,7-dibromocryptolepine cause DNA damage and therefore may not be suitable for pre clinical development as antimalarial agents. Copyright © 2011 Elsevier Ireland Ltd. All rights reserved.

  9. Independent recruitment of a flavin-dependent monooxygenase for safe accumulation of sequestered pyrrolizidine alkaloids in grasshoppers and moths.

    Directory of Open Access Journals (Sweden)

    Linzhu Wang

    Full Text Available Several insect lineages have developed diverse strategies to sequester toxic pyrrolizidine alkaloids from food-plants for their own defense. Here, we show that in two highly divergent insect taxa, the hemimetabolous grasshoppers and the holometabolous butterflies, an almost identical strategy evolved independently for safe accumulation of pyrrolizidine alkaloids. This strategy involves a pyrrolizidine alkaloid N-oxygenase that transfers the pyrrolizidine alkaloids to their respective N-oxide, enabling the insects to avoid high concentrations of toxic pyrrolizidine alkaloids in the hemolymph. We have identified a pyrrolizidine alkaloid N-oxygenase, which is a flavin-dependent monooxygenase, of the grasshopper Zonocerus variegatus. After heterologous expression in E. coli, this enzyme shows high specificity for pyrrolizidine alkaloids of various structural types and for the tropane alkaloid atropine as substrates, a property that has been described previously for a pyrrolizidine alkaloid N-oxygenase of the arctiid moth Grammia geneura. Phylogenetic analyses of insect flavin-dependent monooxygenase sequences suggest that independent gene duplication events preceded the establishment of this specific enzyme in the lineages of the grasshoppers and of arctiid moths. Two further flavin-dependent monooxygenase sequences have been identified from Z. variegatus sharing amino acid identities of approximately 78% to the pyrrolizidine alkaloid N-oxygenase. After heterologous expression, both enzymes are also able to catalyze the N-oxygenation of pyrrolizidine alkaloids, albeit with a 400-fold lower specific activity. With respect to the high sequence identity between the three Z. variegatus sequences this ability to N-oxygenize pyrrolizidine alkaloids is interpreted as a relict of a former bifunctional ancestor gene of which one of the gene copies optimized this activity for the specific adaptation to pyrrolizidine alkaloid containing food plants.

  10. Independent recruitment of a flavin-dependent monooxygenase for safe accumulation of sequestered pyrrolizidine alkaloids in grasshoppers and moths.

    Science.gov (United States)

    Wang, Linzhu; Beuerle, Till; Timbilla, James; Ober, Dietrich

    2012-01-01

    Several insect lineages have developed diverse strategies to sequester toxic pyrrolizidine alkaloids from food-plants for their own defense. Here, we show that in two highly divergent insect taxa, the hemimetabolous grasshoppers and the holometabolous butterflies, an almost identical strategy evolved independently for safe accumulation of pyrrolizidine alkaloids. This strategy involves a pyrrolizidine alkaloid N-oxygenase that transfers the pyrrolizidine alkaloids to their respective N-oxide, enabling the insects to avoid high concentrations of toxic pyrrolizidine alkaloids in the hemolymph. We have identified a pyrrolizidine alkaloid N-oxygenase, which is a flavin-dependent monooxygenase, of the grasshopper Zonocerus variegatus. After heterologous expression in E. coli, this enzyme shows high specificity for pyrrolizidine alkaloids of various structural types and for the tropane alkaloid atropine as substrates, a property that has been described previously for a pyrrolizidine alkaloid N-oxygenase of the arctiid moth Grammia geneura. Phylogenetic analyses of insect flavin-dependent monooxygenase sequences suggest that independent gene duplication events preceded the establishment of this specific enzyme in the lineages of the grasshoppers and of arctiid moths. Two further flavin-dependent monooxygenase sequences have been identified from Z. variegatus sharing amino acid identities of approximately 78% to the pyrrolizidine alkaloid N-oxygenase. After heterologous expression, both enzymes are also able to catalyze the N-oxygenation of pyrrolizidine alkaloids, albeit with a 400-fold lower specific activity. With respect to the high sequence identity between the three Z. variegatus sequences this ability to N-oxygenize pyrrolizidine alkaloids is interpreted as a relict of a former bifunctional ancestor gene of which one of the gene copies optimized this activity for the specific adaptation to pyrrolizidine alkaloid containing food plants.

  11. Application of electron ionization mass spectrometry for mulungu alkaloid analysis

    International Nuclear Information System (INIS)

    Feitosa, Luis Guilherme Pereira; Guaratini, Thais; Lopes, Joao Luis Callegari; Lopes, Norberto Peporine; Bizaro, Aline Cavalli; Silva, Denise Brentan da

    2012-01-01

    Erythrina verna is a medicinal plant used to calm agitation popularly known as mulungu. We purchased the barks of E. verna from a commercial producer and analyzed the alkaloid fraction of the bark by CG-MS and HRESI-MS. Five erythrinian alkaloids were identified: erysotrine, erythratidine, erythratidinone, epimer, and 11-hydroxyeritratidinone. Here we report the compound 11-hydroxyeritratidinone for the first time as a natural product. (author)

  12. Teratology study of derivatives of tetramethylcyclopropyl amide analogues of valproic acid in mice.

    Science.gov (United States)

    Okada, Akinobu; Onishi, Yuko; Aoki, Yoshinobu; Yagen, Boris; Sobol, Eyal; Bialer, Meir; Fujiwara, Michio

    2006-06-01

    Although valproic acid (VPA) is used extensively for treating various kinds of epilepsies, it is well known that it causes neural tube and skeletal defects in both humans and animals. The amide and urea derivatives of the tetramethylcylcopropyl VPA analogue, N-methoxy-2,2,3,3-tetramethylcyclopropanecarboxamide (N-methoxy-TMCD) and 2,2,3,3-tetramethylcyclopropanecarbonylurea (TMC-urea), were synthesized and shown to have a more potent anticonvulsant activity than VPA. The objective of this study was to investigate the teratogenic effects of these compounds in NMRI mice. Pregnant NMRI mice were given a single subcutaneous injection of either VPA, N-methoxy-TMCD, or TMC-urea at 1.8 and 3.6 mmol/kg on gestation day (GD) 8. Cesarean section was performed on GD 18. First, the live fetuses were examined to detect any external malformations, then their skeletons were double-stained for bone and cartilage and subsequently examined. Significant increases in fetal losses and neural tube defects were observed with administration of VPA at 3.6 mmol/kg when compared to the vehicle control. In contrast, upon cesarean section, there were no significant differences between either N-methoxy-TMCD or TMC-urea and the control groups for any parameter. Skeletal examination revealed that a number of the abnormalities were induced by VPA dose-dependently at high rates of incidence. These abnormalities were mainly at the axial skeletal level. However, lower frequencies of skeletal abnormality were observed with N-methoxy-TMCD and TMC-urea than with VPA. In addition to their more potent antiepileptic activity, these findings clearly indicate that N-methoxy-TMCD and TMC-urea are distinctly less teratogenic than VPA in NMRI mice.

  13. O hydrogen bonds in alkaloids

    Indian Academy of Sciences (India)

    An overview of general classification scheme, medicinal importance and crystal structure analysis with emphasis on the role of hydrogen bonding in some alkaloids is presented in this paper. The article is based on a general kind of survey while crystallographic analysis and role of hydrogen bonding are limited to only ...

  14. Interactions between {beta}-carboline alkaloids and bovine serum albumin: Investigation by spectroscopic approach

    Energy Technology Data Exchange (ETDEWEB)

    Nafisi, Shohreh, E-mail: drshnafisi@gmail.com [Department of Chemistry, Islamic Azad University, Central Tehran Branch (IAUCTB), Tehran (Iran, Islamic Republic of); Panahyab, Ataollah [Department of Chemistry, Islamic Azad University, Central Tehran Branch (IAUCTB), Tehran (Iran, Islamic Republic of); Bagheri Sadeghi, Golshan [Department of Biology, Islamic Azad University, Science and Research Branch, Tehran (Iran, Islamic Republic of)

    2012-09-15

    {beta}-Carboline alkaloids are present in medicinal plants such as Peganum harmala L. that have been used as folk medicine in anticancer therapy. BSA is the major soluble protein constituent of the circulatory system, and has many physiological functions including the transport of a variety of compounds. This study is the first attempt to investigate the binding of {beta}-carboline alkaloids to BSA by using a constant protein concentration and varying drug concentrations at pH 7.2. FTIR and UV-Vis spectroscopic methods were used to analyze the binding modes of {beta}-carboline alkaloids, the binding constants and the effects of drug complexation on BSA stability and conformation. Spectroscopic evidence showed that {beta}-carboline alkaloids bind BSA via hydrophobic interaction and van der Waals contacts along with H-bonding with the -NH groups, with overall binding constants of K{sub harmine-BSA}=2.04 Multiplication-Sign 10{sup 4} M{sup -1}, K{sub tryptoline-BSA}=1.2 Multiplication-Sign 10{sup 4} M{sup -1}, K{sub harmaline-BSA}=5.04 Multiplication-Sign 10{sup 3} M{sup -1}, K{sub harmane-BSA}=1.41 Multiplication-Sign 10{sup 3} M{sup -1} and K{sub harmalol-BSA}=1.01 Multiplication-Sign 10{sup 3} M{sup -1}, assuming that there is one drug molecule per protein. The BSA secondary structure was altered with a major decrease of {alpha}-helix from 64% (free protein) to 59% (BSA-harmane), 56% (BSA-harmaline and BSA-harmine), 55% (BSA-tryptoline), 54% (BSA-harmalol) and {beta}-sheet from 15% (free protein) to 6-8% upon {beta}-carboline alkaloids complexation, inducing a partial protein destabilization. - Highlights: Black-Right-Pointing-Pointer We model the binding of {beta}-carboline alkaloids to BSA by using the spectroscopic methods. Black-Right-Pointing-Pointer We investigate the effects of drug complexation on BSA stability and conformation. Black-Right-Pointing-Pointer A partial protein destabilization occurred at high alkaloids concentration. Black

  15. Detection of Pyrrolizidine Alkaloid DNA Adducts in Livers of Cattle Poisoned with Heliotropium europaeum.

    Science.gov (United States)

    Fu, Peter P; Xia, Qingsu; He, Xiaobo; Barel, Shimon; Edery, Nir; Beland, Frederick A; Shimshoni, Jakob A

    2017-03-20

    Pyrrolizidine alkaloids are among the most common poisonous plants affecting livestock, wildlife, and humans. Exposure of humans and livestock to toxic pyrrolizidine alkaloids through the intake of contaminated food and feed may result in poisoning, leading to devastating epidemics. During February 2014, 73 mixed breed female beef cows from the Galilee region of Israel were accidently fed pyrrolizidine alkaloid contaminated hay for 42 days, resulting in the sudden death of 24 cows over a period of 63 days. The remaining cows were slaughtered 2.5 months after the last ingestion of the contaminated hay. In this study, we report the histopathological analysis of the livers from five of the slaughtered cows and quantitation of pyrrolizidine alkaloid-derived DNA adducts from their livers and three livers of control cows fed with feed free of weeds producing pyrrolizidine alkaloids. Histopathological examination revealed that the five cows suffered from varying degrees of bile duct proliferation, fibrosis, and megalocytosis. Selected reaction monitoring HPLC-ES-MS/MS analysis indicated that (±)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived DNA adducts were formed in all five livers. The livers from the three control cows did not have any liver damage nor any indication of DHP-DNA adduct formed. These results confirm that the toxicity observed in these cattle was caused by pyrrolizidine alkaloid poisoning and that pyrrolizidine alkaloid-derived DNA adducts could still be detected and quantified in the livers of the chronically poisoned cows 2.5 months after their last exposure to the contaminated feed, suggesting that DHP-derived DNA adducts can serve as biomarkers for pyrrolizidine alkaloid exposure and poisoning.

  16. Peculiarities of tropane alkaloids determination in Datura Stramonium L. leaves

    Directory of Open Access Journals (Sweden)

    Володимир Анатолійович Міщенко

    2015-12-01

    Full Text Available The questions of the search, pharmacological activity and standardization of natural extracts are appropriate and important for national pharmaceutical science and practice. Since 2000, one of the key points of the Action Plan to ensure the integration of Ukraine into the European Union is development of the State Pharmacopoeia of Ukraine harmonized with the European Pharmacopoeia (PhEur.Aim: A comparative analysis of herbal material according to the methods for tropane group alkaloids determination, as described in the PhEur and in the 11th Edition of USSR Pharmacopoeia Monographs «Stramonium leaf».Methods: Datura leaves samples have been harvested during 2010-2012 in different regions of Ukraine for experimental research. Identification of tropane group alkaloids was carried out by the method of thin-layer chromatography (TLC and by Vitali-Morin colour reaction. According to the PhEur method, firstly Dragendorff reagent and then Sodium nitrite solutions were used for the TLC plates spraying. Alkaloids assay was carried out by alkalimetry method with indicator determination of equivalence point.Results: Datura leaves qualitative features, defined by PhEur and the 11th Edition of USSR Pharmacopoeia Monographs «Stramonium leaf», as well as their rationing have been analyzed. Certain differences concerning regulated quality parameters of herbal material have been determined. A comparative analysis of the natural extracts by described in the given normative documents methods for determination of tropane group alkaloids content has been done. After spraying the TLC plates with Sodium nitrite solution, red-brown zones corresponding Hyoscyamine were determined. Hyoscine zones were characterized by less intense color. As a result of quantitative determination it was determined that the alkaloids content in analyzed Datura leaves samples was within the limits regulated by the PhEur and the 11th Edition of USSR Pharmacopoeia – more than 0

  17. Accelerating Inspire

    CERN Document Server

    AUTHOR|(CDS)2266999

    2017-01-01

    CERN has been involved in the dissemination of scientific results since its early days and has continuously updated the distribution channels. Currently, Inspire hosts catalogues of articles, authors, institutions, conferences, jobs, experiments, journals and more. Successful orientation among this amount of data requires comprehensive linking between the content. Inspire has lacked a system for linking experiments and articles together based on which accelerator they were conducted at. The purpose of this project has been to create such a system. Records for 156 accelerators were created and all 2913 experiments on Inspire were given corresponding MARC tags. Records of 18404 accelerator physics related bibliographic entries were also tagged with corresponding accelerator tags. Finally, as a part of the endeavour to broaden CERN's presence on Wikipedia, existing Wikipedia articles of accelerators were updated with short descriptions and links to Inspire. In total, 86 Wikipedia articles were updated. This repo...

  18. Application of Liquid Chromatography/Ion Trap Mass Spectrometry Technique to Determine Ergot Alkaloids in Grain Products.

    Science.gov (United States)

    Bryła, Marcin; Szymczyk, Krystyna; Jędrzejczak, Renata; Roszko, Marek

    2015-03-01

    A liquid chromatography/ion trap mass spectrometry-based method to determine six ergot alkaloids and their isomers is presented. The samples were cleaned on neutral alumina-based solid-phase extraction cartridges. The following method parameters were obtained (depending on the analyte and spiking level): method recovery from 63.0 to 104.6%, relative standard deviation below 18%, linear range from 1 to 325 µg/kg, linear correlation coefficient not less than 0.98. The developed analytical procedure was applied to determine the levels of ergot alkaloids in 65 samples of selected rye-based food products (flour - 34 samples, bran - 12 samples, rye - 18 samples, flakes - 1 sample). Measurable levels of alkaloids were found in majority of the analysed samples, particularly in rye flour. Additionally, alkaloids were determined in ergot sclerotia isolated from rye grains. Total content was nearly 0.01% (97.9 mg/kg). However, the alkaloid profile was dominated by ergocristine at 45.6% (44.7 mg/kg), an alkaloid not commonly found in the tested food products. Ergocorninine at 0.2% (0.2 mg/kg) was the least abundant alkaloid.

  19. Alkaloid-Containing Plants Poisonous to Cattle and Horses in Europe

    Directory of Open Access Journals (Sweden)

    Cristina Cortinovis

    2015-12-01

    Full Text Available Alkaloids, nitrogen-containing secondary plant metabolites, are of major interest to veterinary toxicology because of their occurrence in plant species commonly involved in animal poisoning. Based on epidemiological data, the poisoning of cattle and horses by alkaloid-containing plants is a relatively common occurrence in Europe. Poisoning may occur when the plants contaminate hay or silage or when forage alternatives are unavailable. Cattle and horses are particularly at risk of poisoning by Colchicum autumnale (meadow saffron, Conium maculatum (poison hemlock, Datura stramonium (jimson weed, Equisetum palustre (marsh horsetail, Senecio spp. (ragwort and groundsel and Taxus baccata (European yew. This review of poisonous alkaloid-containing plants describes the distribution of these plants, conditions under which poisoning occurs, active toxic principles involved and subsequent clinical signs observed.

  20. Classification of Opium by UPLC-Q-TOF Analysis of Principal and Minor Alkaloids.

    Science.gov (United States)

    Liu, Cuimei; Hua, Zhendong; Bai, Yanping

    2016-11-01

    Opium is the raw material for the production of heroin, and the characterization of opium seizures through laboratory analysis is a valuable tool for law enforcement agencies to trace clandestine opium production and trafficking. In this work, a method for opium profiling based on the relative content of five principal and 14 minor opium alkaloids was developed and validated. UPLC-Q-TOF was adopted in alkaloid analysis for its high selectivity and sensitivity, which facilitated the sample preparation and testing. The authentic sample set consisted of 100 "Myanmar" and 45 "Afghanistan" opium seizures; based on the data set of the 19 alkaloid variables in them, a partial least squares discriminant analysis classification model was successfully achieved. Minor alkaloids were found to be vitally important for opium profiling, although combined use of both principal and minor alkaloids resulted in the best geographical classification result. The developed method realized a simple and accurate way to differentiate opium from Myanmar and Afghanistan, which may find wide application in forensic laboratories. © 2016 American Academy of Forensic Sciences.

  1. Analysis of Amaryllidaceae alkaloids from Zephyranthes grandiflora by GC/MS and their cholinesterase activity

    Directory of Open Access Journals (Sweden)

    Lucie Cahlíková

    2011-05-01

    Full Text Available Amaryllidaceae are known as ornamental plants, furthermore some species of this family contain galanthamine, an acetylcholinesterase inhibitor approved for the treatment of Alzheimer's disease, and other alkaloids with interesting pharmacological activity. The chemical composition of alkaloids from Zephyranthes grandiflora Lindl. was analyzed by GC/MS. Seven known compounds, belonging to five structural types of Amaryllidaceae alkaloids, were identified. The alkaloid extract from the bulbs showed promising cholinesterase inhibitory activities against human blood acetylcholinesterase (HuAChE; IC50 39.2±3.0 µg/mL and human plasma butyrylcholinesterase (HuBuChE; IC50 356±9.3 µg/mL.

  2. Analysis of Amaryllidaceae alkaloids from Zephyranthes grandiflora by GC/MS and their cholinesterase activity

    Directory of Open Access Journals (Sweden)

    Lucie Cahlíková

    2011-08-01

    Full Text Available Amaryllidaceae are known as ornamental plants, furthermore some species of this family contain galanthamine, an acetylcholinesterase inhibitor approved for the treatment of Alzheimer's disease, and other alkaloids with interesting pharmacological activity. The chemical composition of alkaloids from Zephyranthes grandiflora Lindl. was analyzed by GC/MS. Seven known compounds, belonging to five structural types of Amaryllidaceae alkaloids, were identified. The alkaloid extract from the bulbs showed promising cholinesterase inhibitory activities against human blood acetylcholinesterase (HuAChE; IC50 39.2±3.0 µg/mL and human plasma butyrylcholinesterase (HuBuChE; IC50 356±9.3 µg/mL.

  3. Temporal and spatial variation in alkaloid levels in Achnatherum robustum, a native grass infected with the endophyte Neotyphodium.

    Science.gov (United States)

    Faeth, Stanley H; Gardner, Dale R; Hayes, Cinnamon J; Jani, Andrea; Wittlinger, Sally K; Jones, Thomas A

    2006-02-01

    The native North American perennial grass Achnatherum robustum (Vasey) Barkworth [= Stipa robusta (Vasey) Scribn.] or sleepygrass is toxic and narcotic to livestock. The causative agents are alkaloidal mycotoxins produced from infections by a systemic and asexual Neotyphodium endophyte. Recent studies suggest that toxicity is limited across the range of sleepygrass in the Southwest USA. We sampled 17 populations of sleepygrass with varying distance from one focal population known for its high toxicity levels near Cloudcroft, NM, USA. For some, we sampled individual plants twice within the same growing season and over successive years (2001-2004). We also determined infection levels in each population. In general, all populations were highly infected, but infection levels were more variable near the focal population. Only infected plants within populations near the Cloudcroft area produced alkaloids. The ergot alkaloid, ergonovine, comprised the bulk of the alkaloids, with lesser amounts of lysergic and isolysergic acid amides and ergonovinine alkaloids. Levels of all alkaloids were positively correlated among individual plants within and between growing seasons. Infected plants that produced no alkaloids in 1 yr did not produce any alkaloids within the same growing season or in other years. Levels of alkaloids in sleepygrass populations declined with distance from the Cloudcroft population, although infection levels increased. Infected plants in populations in northern New Mexico and southern Colorado produced no alkaloids at all despite 100% infectivity. Our results suggest that only specific Neotyphodium haplotypes or specific Neotyphodium-grass combinations produce ergot alkaloids in sleepygrass. The Neotyphodium haplotype or host-endophyte combination that produces toxic levels of alkaloids appears restricted to one locality across the range of sleepygrass. Because of the wide variation in alkaloid levels among populations, interactions between the endophyte

  4. New insights into Vinca alkaloids resistance mechanism and circumvention in lung cancer.

    Science.gov (United States)

    Zhang, Ying; Yang, Shao-Hui; Guo, Xiu-Li

    2017-12-01

    Nowadays, lung cancer, as a health problem in worldwide, has high mortality both in men and women. Despite advances in diagnosis and surgical techniques of lung cancer in recent decades, chemotherapy is still a fundamentally and extensively useful strategy. Vinca alkaloids are a class of important and widely used drugs in the treatment of lung cancer, targeting on the Vinca binding site at the exterior of microtubule plus ends. Either intrinsic or acquired resistance to chemotherapy of Vinca alkaloids has been a major obstacle to the treatment of lung cancer, which arose great interests in studies of understanding and overcoming resistance. In this review, we focused on the application and resistance mechanisms of the Vinca alkaloids such as vinblastine, vincristine, vinorelbine and vinflunine in lung cancer. We reviewed characteristic resistance mechanisms in lung cancer including over-expression of ATP-binding cassette (ABC) transporters P-glycoprotein and structural, functional or expression alterations of β-tubulin (βII, βIII, βIV) which may devote to the development of acquired resistance to the Vinca alkaloids; multidrug-resistance proteins (MRP1, MRP2, MRP3) and RLIP76 protein have also been identified that probably play a significant role in intrinsic resistance. Lung resistance-related protein (LRP) is contributed to lung cancer therapy resistance, but is not deal with the Vinca alkaloids resistance in lung cancer. Understanding the principle of the Vinca alkaloids in clinical application and mechanisms of drug resistance will support individualized lung cancer therapy and improve future therapies. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  5. Genotoxic Pyrrolizidine Alkaloids — Mechanisms Leading to DNA Adduct Formation and Tumorigenicity

    Directory of Open Access Journals (Sweden)

    Ming W. Chou

    2002-09-01

    Full Text Available Abstract: Plants that contain pyrrolizidine alkaloids are widely distributed in the world. Although pyrrolizidine alkaloids have been shown to be genotoxic and tumorigenic in experimental animals, the mechanisms of actions have not been fully understood. The results of our recent mechanistic studies suggest that pyrrolizidine alkaloids induce tumors via a genotoxic mechanism mediated by 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5Hpyrrolizine (DHP-derived DNA adduct formation. This mechanism may be general to most carcinogenic pyrrolizidine alkaloids, including the retronecine-, heliotridine-, and otonecinetype pyrrolizidine alkaloids. It is hypothesized that these DHP-derived DNA adducts are potential biomarkers of pyrrolizidine alkaloid tumorigenicity. The mechanisms that involve the formation of DNA cross-linking and endogenous DNA adducts are also discussed.

  6. Hybrid Monoterpenoid Indole Alkaloids Obtained as Artifacts from Rauvolfia tetraphylla.

    Science.gov (United States)

    Gao, Yuan; Zhou, Dong-Sheng; Hai, Ping; Li, Yan; Wang, Fei

    2015-10-01

    Five new hybrid monoterpenoid indole alkaloids bearing an unusual 2,2-dimethyl-4-oxopiperidin-6-yl moiety, namely rauvotetraphyllines F-H (1, 3, 4), 17-epi-rauvotetraphylline F (2) and 21-epi-rauvotetraphylline H (5), were isolated from the aerial parts of Rauvolfia tetraphylla. Their structures were established by extensive spectroscopic analysis. The new alkaloids were evaluated for their cytotoxicity in vitro against five human cancer cell lines.

  7. Novel β-Carboline Alkaloid from Peganum Harmala As Antibacterial Agent

    International Nuclear Information System (INIS)

    Abdel Aziz, H.G.; Abdel Kader, S.M.; El-Sayed, M.M.; EL-Malt, E.A.; Shaker, E.S.

    2011-01-01

    A novel β-carboline alkaloid isolated from the aerial parts of Peganum harmala L. (Gen: Phyeophylaceae) have been characterized as l-thioformyl-8-β-D-glucopyranoside-bis-2,3-dihydro-isopyridinopyrrol. It is one of β-carboline alkaloids derivatives. The chemical structure was elucidated on the basis of elementary analysis and spectroscopic studies (UV, IR, 1 H-NMR and MS). The isolated compound showed significant antibacterial activity against Streptococcus pyogenus.

  8. Novel {beta}-Carboline Alkaloid from Peganum Harmala As Antibacterial Agent

    Energy Technology Data Exchange (ETDEWEB)

    Abdel Aziz, H G; Abdel Kader, S M; El-Sayed, M M; EL-Malt, E A; Shaker, E S [Chem. Dept., Fac. Agric., Minia Univ., Minia (Egypt)

    2011-07-01

    A novel {beta}-carboline alkaloid isolated from the aerial parts of Peganum harmala L. (Gen: Phyeophylaceae) have been characterized as l-thioformyl-8-{beta}-D-glucopyranoside-bis-2,3-dihydro-isopyridinopyrrol. It is one of {beta}-carboline alkaloids derivatives. The chemical structure was elucidated on the basis of elementary analysis and spectroscopic studies (UV, IR, {sup 1}H-NMR and MS). The isolated compound showed significant antibacterial activity against Streptococcus pyogenus.

  9. Dehydropyrrolizidine alkaloid toxicity, cytotoxicity, and carcinogenicity

    Science.gov (United States)

    Dehyro-pyrrolizidine alkaloid (PA)-containing plants compose about 5% of the world’s flowering plants and they commonly poison livestock, wildlife and humans. Previous work has produced considerable understanding of PA toxicity, species susceptibility, conditions and routes of exposure, toxin metab...

  10. Anti-inflammatory Activity of Pyrrolizidine Alkaloids from the Leaves of Madhuca pasquieri (Dubard).

    Science.gov (United States)

    Hoang, Le Son; Tran, Manh Hung; Lee, Joo Sang; To, Dao Cuong; Nguyen, Van Thu; Kim, Jeong Ah; Lee, Jeong Hyung; Woo, Mi Hee; Min, Byung Sun

    2015-01-01

    A novel pyrrolizidine alkaloids, madhumidine A (1), and two known alkaloids, lindelofidine benzoic acid ester (2) and minalobine B (3) were isolated from the leaves of Madhuca pasquieri (Dubard) H. J. LAM. The chemical structures of these alkaloids were established mainly by NMR techniques and mass spectrometry. Their anti-inflammatory activity was evaluated against lipopolysaccharide-induced nitric oxide production in macrophage RAW264.7 cell. In addition, the cytotoxic activity of all isolated compounds was tested against a panel of cancer cell lines.

  11. Soil-borne microorganisms and soil-type affect pyrrolizidine alkaloids in Jacobaea vulgaris

    NARCIS (Netherlands)

    Joosten, L.; Mulder, P.P.J.; Klinkhamer, P.G.L.; Van Veen, J.A.

    2009-01-01

    Secondary metabolites like pyrrolizidine alkaloids (PAs) play a crucial part in plant defense. We studied the effects of soil-borne microorganisms and soil-type on pyrrolizidine alkaloids in roots and shoots of Jacobaea vulgaris. We used clones of two genotypes from a dune area (Meijendel),

  12. Incorporation of 2H-labelled cadaverines into the quinolizidine alkaloids in Baptisia australis

    International Nuclear Information System (INIS)

    Robins, D.J.; Sheldrake, G.N.

    1988-01-01

    The incorporation of 2 H-labelled cadaverines into the quinolizidine alkaloids, sparteine and N-methylcytisine, in Baptisia australis has been studied in order to gain more information about the formation of these alkaloids. (author)

  13. Potential of plant alkaloids as dengue ns3 protease inhibitors: Molecular docking and simulation approach

    Directory of Open Access Journals (Sweden)

    Muhammad Tahir ul Qamar

    2014-08-01

    Full Text Available Dengue infection has become a worldwide health problem and infection rate is increasing each year. Alkaloids are important phytochemicals of medicinal plant and can be used as vaccine candidates for viruses. Therefore, present study was designed to find potential alkaloids inhibitors against the Dengue virus NS2B/NS3 protease which can inhibit the viral replication inside the host cell. Through molecular docking it was investigated that most of the alkaloids bound deeply in the binding pocket of Dengue virus NS2B/NS3 protease and had potential interactions with catalytic triad. Five alkaloids (6’-desmethylthalifaboramin; 3,5-dihydroxythalifaboramine; Betanin; Reserpic acid and Tubulosine successfully blocked the catalytic triad of NS2B/NS3 protease and these alkaloids can serve as a potential drug candidate to stop viral replication. It can be concluded from this study that these alkaloids could serve as important inhibitors to inhibit the replication of DENV and need further in-vitro investigations to confirm their efficacy and drug ability.

  14. Physicists Get INSPIREd: INSPIRE Project and Grid Applications

    International Nuclear Information System (INIS)

    Klem, Jukka; Iwaszkiewicz, Jan

    2011-01-01

    INSPIRE is the new high-energy physics scientific information system developed by CERN, DESY, Fermilab and SLAC. INSPIRE combines the curated and trusted contents of SPIRES database with Invenio digital library technology. INSPIRE contains the entire HEP literature with about one million records and in addition to becoming the reference HEP scientific information platform, it aims to provide new kinds of data mining services and metrics to assess the impact of articles and authors. Grid and cloud computing provide new opportunities to offer better services in areas that require large CPU and storage resources including document Optical Character Recognition (OCR) processing, full-text indexing of articles and improved metrics. D4Science-II is a European project that develops and operates an e-Infrastructure supporting Virtual Research Environments (VREs). It develops an enabling technology (gCube) which implements a mechanism for facilitating the interoperation of its e-Infrastructure with other autonomously running data e-Infrastructures. As a result, this creates the core of an e-Infrastructure ecosystem. INSPIRE is one of the e-Infrastructures participating in D4Science-II project. In the context of the D4Science-II project, the INSPIRE e-Infrastructure makes available some of its resources and services to other members of the resulting ecosystem. Moreover, it benefits from the ecosystem via a dedicated Virtual Organization giving access to an array of resources ranging from computing and storage resources of grid infrastructures to data and services.

  15. Pyrrolizidine Alkaloids: Potential Role in the Etiology of Cancers, Pulmonary Hypertension, Congenital Anomalies, and Liver Disease.

    Science.gov (United States)

    Edgar, John A; Molyneux, Russell J; Colegate, Steven M

    2015-01-20

    Large outbreaks of acute food-related poisoning, characterized by hepatic sinusoidal obstruction syndrome, hemorrhagic necrosis, and rapid liver failure, occur on a regular basis in some countries. They are caused by 1,2-dehydropyrrolizidine alkaloids contaminating locally grown grain. Similar acute poisoning can also result from deliberate or accidental consumption of 1,2-dehydropyrrolizidine alkaloid-containing herbal medicines, teas, and spices. In recent years, it has been confirmed that there is also significant, low-level dietary exposure to 1,2-dehydropyrrolizidine alkaloids in many countries due to consumption of common foods such as honey, milk, eggs, salads, and meat. The level of 1,2-dehydropyrrolizidine alkaloids in these foods is generally too low and too intermittent to cause acute toxicity. However, these alkaloids are genotoxic and can cause slowly developing chronic diseases such as pulmonary arterial hypertension, cancers, cirrhosis, and congenital anomalies, conditions unlikely to be easily linked with dietary exposure to 1,2-dehydropyrrolizidine alkaloids, especially if clinicians are unaware that such dietary exposure is occurring. This Perspective provides a comprehensive review of the acute and chronic toxicity of 1,2-dehydropyrrolizidine alkaloids and their potential to initiate certain chronic diseases, and suggests some associative considerations or indicators to assist in recognizing specific cases of diseases that may have resulted from dietary exposure to these hazardous natural substances. If it can be established that low-level dietary exposure to 1,2-dehydropyrrolizidine alkaloids is a significant cause of some of these costly and debilitating diseases, then this should lead to initiatives to reduce the level of these alkaloids in the food chain.

  16. [A method for the determination of ergot alkaloids in food].

    Science.gov (United States)

    Klug, C; Baltes, W; Krönert, W; Weber, R

    1988-02-01

    A suitable method has been developed for the routine analysis of the ergot alkaloids ergometrine, ergometrinine, ergosine, ergosinine, ergotamine, ergotaminine, ergocornine, ergocorninine, alpha-ergocryptine, alpha-ergocryptinine, beta-ergocryptine, beta-ergocryptinine, ergocristine and ergocristinine in cereal products. The method consists of food extraction, cleaning of the crude extract by a modified form of the Extrelut method, and identification and quantitative determination of the alkaloids by high pressure liquid chromatography (HPLC). The results are confirmed by thin layer chromatography (TLC) and gas-chromatography/mass spectrometry (GC/MS). Market investigations have shown contaminations in ecological as well as in conventional products, with rye products mainly being contaminated. Within the EEC, a maximum value of 0.05% ergot respectively a total alkaloid content of 1 mg/kg in cereals used for food production is prescribed. This value was not exceeded in any of the investigated samples.

  17. A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf.

    Science.gov (United States)

    da Silva, Gustavo; Martinho, Ana; Soengas, Raquel González; Duarte, Ana Paula; Serrano, Rita; Gomes, Elsa Teixeira; Silva, Olga

    2015-10-01

    The isolation and structural elucidation of a macrocyclic alkaloid, characterized by the presence of a 13-membered macrolactam ring containing a spermidine unit N-linked to a benzoyl group is hereby reported. The structure of this previously unknown spermidine alkaloid isolated from Gymnosporia arenicola (Celastraceae) leaves has been elucidated by (1)H and (13)C NMR spectroscopy (including bidimensional analysis) and further characterized by high-resolution mass spectrometry and polarimetry. A route for the biosynthesis of this new bioactive macrocycle is proposed and the cytotoxicity of the compound was evaluated against two ATCC cell lines - one normal-derived (MCF10A) and one cancer-derived cell line (MCF7) - using the MTT assay. The alkaloid revealed to be non-cytotoxic against both cell lines. The IC50 values from the cells were also determined. Copyright © 2015 Elsevier B.V. All rights reserved.

  18. Application of Liquid Chromatography/Ion Trap Mass Spectrometry Technique to Determine Ergot Alkaloids in Grain Products

    Directory of Open Access Journals (Sweden)

    Krystyna Szymczyk

    2015-01-01

    Full Text Available A liquid chromatography/ion trap mass spectrometry-based method to determine six ergot alkaloids and their isomers is presented. The samples were cleaned on neutral alumina-based solid-phase extraction cartridges. The following method parameters were obtained (depending on the analyte and spiking level: method recovery from 63.0 to 104.6 %, relative standard deviation below 18 %, linear range from 1 to 325 μg/kg, linear correlation coefficient not less than 0.98. The developed analytical procedure was applied to determine the levels of ergot alkaloids in 65 samples of selected rye-based food products (flour– 34 samples, bran – 12 samples, rye – 18 samples, flakes – 1 sample. Measurable levels of alkaloids were found in majority of the analysed samples, particularly in rye flour. Additionally, alkaloids were determined in ergot sclerotia isolated from rye grains. Total content was nearly 0.01 % (97.9 mg/kg. However, the alkaloid profi le was dominated by ergocristine at 45.6 % (44.7 mg/kg, an alkaloid not commonly found in the tested food products. Ergocorninine at 0.2 % (0.2 mg/kg was the least abundant alkaloid.

  19. Quantitative skeletal scintiscanning

    International Nuclear Information System (INIS)

    Haushofer, R.

    1982-01-01

    330 patients were examined by skeletal scintiscanning with sup(99m)Tc pyrophosphate and sup(99m)methylene diphosphonate in the years between 1977 and 1979. Course control examinations were carried out in 12 patients. The collective of patients presented with primary skeletal tumours, metastases, inflammatory and degenerative skeletal diseases. Bone scintiscanning combined with the ''region of interest'' technique was found to be an objective and reproducible technique for quantitative measurement of skeletal radioactivity concentrations. The validity of nuclear skeletal examinations can thus be enhanced as far as diagnosis, course control, and differential diagnosis are concerned. Quantitative skeletal scintiscanning by means of the ''region of interest'' technique has opened up a new era in skeletal diagnosis by nuclear methods. (orig./MG) [de

  20. Variable Alkaloid Defenses in the Dendrobatid Poison Frog Oophaga pumilio are Perceived as Differences in Palatability to Arthropods.

    Science.gov (United States)

    Bolton, Sarah K; Dickerson, Kelsie; Saporito, Ralph A

    2017-03-01

    Conspicuously colored dendrobatid frogs sequester alkaloid defenses from dietary arthropods, resulting in considerable alkaloid variation among populations; however, little is known about how variation is perceived as a defense against predators. Previous studies have found variable alkaloids in the dendrobatid Oophaga pumilio to be associated with differences in toxicity to laboratory mice, suggesting variable defenses are important. Arthropods are natural predators that use chemoreception to detect prey, including frogs, and may therefore perceive variation in alkaloid profiles as differences in palatability. The goal of the present study is to determine how arthropods respond to variable alkaloid defenses in O. pumilio. Frog alkaloids were sampled from individual O. pumilio from ten geographic locations throughout the Bocas del Toro region of Panama and the Caribbean coast of Costa Rica. Alkaloid extracts were used in feeding bioassays with the vinegar fly Drosophila melanogaster and the ant Ectatomma ruidum. Both species of arthropods fed significantly less on frog alkaloid extracts when compared to controls, and differences in alkaloid palatability were observed among frog populations, as well as between sexes and life stages within a population. Differences in alkaloid quantity, richness, and type were the main predictors of arthropod palatability. Our findings also represent the first direct evidence of a palatability spectrum in a vertebrate that sequesters chemical defenses from dietary sources. Further, the presence of a palatability spectrum suggests that variable alkaloid defenses in O. pumilio are ecologically relevant and play an important role in natural predator-prey interactions, particularly with respect to arthropod predators.

  1. Survival and development of Heliothis virescens (Lepidoptera: Noctuidae) larvae on isogenic tobacco lines with different levels of alkaloids.

    Science.gov (United States)

    Jackson, D Michael; Johnson, A W; Stephenson, M G

    2002-12-01

    Levels of pyridine alkaloids were measured in 18 tobacco, Nicotiana tabacum L., entries from three parental isolines ('NC 95', 'SC 58', and 'Coker 139'), grown at Tifton, GA, Florence, SC, and Oxford, NC, in 1991. Levels of alkaloids in bud leaves (first fully unfolded leaf below the apical leaf bud) were negatively correlated to natural infestation ratings of tobacco budworm larvae, Heliothis virescens (F.), 7 wk after transplanting. For artificially infested bud leaves at Oxford, there was a significant negative correlation between levels of total alkaloids and larval weights after 1 wk of feeding. In 1992, four entries from the 'NC 95' isoline were grown at Oxford, and samples for alkaloid analyses were taken every 2 wk at several leaf positions on each plant. During weeks 4, 8, 12, and 16, second instar tobacco budworms were caged on individual, intact leaves inside perforated plastic bags in the field. The survival and development of tobacco budworm larvae after 1 wk were negatively correlated with levels of alkaloids at the various leaf positions. Larvae survived better and grew faster on the bud leaves of each entry where alkaloid levels were lower than they did on leaves further down the stalk where alkaloid levels were higher. More larvae survived on the lower leaves of the low alkaloid lines than on the lower leaves of the high alkaloid lines. Even moderate increases in pyridine alkaloids had negative effects on tobacco budworm survival and development. Nicotine constituted >97% of the pyridine alkaloids in the 'NC95' isoline each year.

  2. Hybrid Monoterpenoid Indole Alkaloids Obtained as Artifacts from Rauvolfia tetraphylla

    OpenAIRE

    Gao, Yuan; Zhou, Dong-Sheng; Hai, Ping; Li, Yan; Wang, Fei

    2015-01-01

    Abstract Five new hybrid monoterpenoid indole alkaloids bearing an unusual 2,2-dimethyl-4-oxopiperidin-6-yl moiety, namely rauvotetraphyllines F–H (1, 3, 4), 17-epi-rauvotetraphylline F (2) and 21-epi-rauvotetraphylline H (5), were isolated from the aerial parts of Rauvolfia tetraphylla. Their structures were established by extensive spectroscopic analysis. The new alkaloids were evaluated for their cytotoxicity in vitro against five human cancer cell lines. Graphical Abstract Electronic supp...

  3. The Effect of Alkaloidal Fraction from Annona squamosa L. against Pathogenic Bacteria with Antioxidant Activities

    Directory of Open Access Journals (Sweden)

    Abdulmushin M. Shami

    2017-12-01

    Full Text Available Background: Annona squamosa is used in different places such as India as a general tonic to enrich blood, relieve vomiting, cancer, as a vermicide, for skin complaints and also applied to wounds and ulcers. The purpose of the study was to evaluate the antibacterial and antioxidant properties from of the alkaloidal fraction of A. squamosa. Methods: Well diffusion assay, minimum inhibitory concentration and the minimum bactericidal concentration (MBC were used to evaluate antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus cereus, Pseudomonas aeruginosa, MRSA and Helicobacter pylori. DPPH and SOD assays were used to evaluate antioxidant activity. LC-MS analysis was used to identify alkaloids and scanning electron microscopy studies that revealed mode of action. Results: Alkaloidal fraction of A. squamosa exhibited significant inhibition against the tested bacteria. Extracted alkaloids from the leaves of A. squamosa showed high level of antioxidant activities. LC-MS analyses of alkaloids of the plant were identified as corydine, sanjoinine, norlaureline, norcodeine, oxanalobine and aporphine in the leaves of A. squamosa. SEM analysis of the interaction of these substances with the bacteria showed morphological changes of cell wall and lysis of the targeted bacterial cells. Conclusions: It could be concluded that the alkaloids isolated from A. squamosa showed good antibacterial and antioxidant activity. The results suggest the alkaloids can be a new source of antimicrobial agents against pathogenic bacteria and antioxidant source.

  4. Full structure assignments of pyrrolizidine alkaloid DNA adducts and mechanism of tumor initiation.

    Science.gov (United States)

    Zhao, Yuewei; Xia, Qingsu; Gamboa da Costa, Gonçalo; Yu, Hongtao; Cai, Lining; Fu, Peter P

    2012-09-17

    Pyrrolizidine alkaloid-containing plants are widespread in the world and are probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids are among the first chemical carcinogens identified in plants. Previously, we determined that metabolism of pyrrolizidine alkaloids in vivo and in vitro generated a common set of DNA adducts that are responsible for tumor induction. Using LC-ESI/MS/MS analysis, we previously determined that four DNA adducts (DHP-dG-3, DHP-dG-4, DHP-dA-3, and DHP-dA-4) were formed in rats dosed with riddelliine, a tumorigenic pyrrolizidine alkaloid. Because of the lack of an adequate amount of authentic standards, the structures of DHP-dA-3 and DHP-dA-4 were not elucidated, and the structural assignment for DHP-dG-4 warranted further validation. In this study, we developed an improved synthetic methodology for these DNA adducts, enabling their full structural elucidation by mass spectrometry and NMR spectroscopy. We determined that DHP-dA-3 and DHP-dA-4 are a pair of epimers of 7-hydroxy-9-(deoxyadenosin-N(6)-yl) dehydrosupinidine, while DHP-dG-4 is 7-hydroxy-9-(deoxyguanosin-N(2)-yl)dehydrosupinidine, an epimer of DHP-dG-3. With the structures of these DNA adducts unequivocally elucidated, we conclude that cellular DNA preferentially binds dehydropyrrolizidine alkaloid, for example, dehydroriddelliine, at the C9 position of the necine base, rather than at the C7 position. We also determined that DHP-dA-3 and DHP-dA-4, as well as DHP-dG-3 and DHP-dG-4, are interconvertible. This study represents the first report with detailed structural assignments of the DNA adducts that are responsible for pyrrolizidine alkaloid tumor induction on the molecular level. A mechanism of tumor initiation by pyrrolizidine alkaloids is consequently fully determined.

  5. Differences in Tolerance to Host Cactus Alkaloids in Drosophila koepferae and D. buzzatii

    Science.gov (United States)

    Soto, Ignacio M.; Carreira, Valeria P.; Corio, Cristian; Padró, Julián; Soto, Eduardo M.; Hasson, Esteban

    2014-01-01

    The evolution of cactophily in the genus Drosophila was a major ecological transition involving over a hundred species in the Americas that acquired the capacity to cope with a variety of toxic metabolites evolved as feeding deterrents in Cactaceae. D. buzzatii and D. koepferae are sibling cactophilic species in the D. repleta group. The former is mainly associated with the relatively toxic-free habitat offered by prickly pears (Opuntia sulphurea) and the latter has evolved the ability to use columnar cacti of the genera Trichocereus and Cereus that contain an array of alkaloid secondary compounds. We assessed the effects of cactus alkaloids on fitness-related traits and evaluated the ability of D. buzzatii and D. koepferae to exploit an artificial novel toxic host. Larvae of both species were raised in laboratory culture media to which we added increasing doses of an alkaloid fraction extracted from the columnar cactus T. terschekii. In addition, we evaluated performance on an artificial novel host by rearing larvae in a seminatural medium that combined the nutritional quality of O. sulphurea plus amounts of alkaloids found in fresh T. terschekii. Performance scores in each rearing treatment were calculated using an index that took into account viability, developmental time, and adult body size. Only D. buzzatii suffered the effects of increasing doses of alkaloids and the artificial host impaired viability in D. koepferae, but did not affect performance in D. buzzatii. These results provide the first direct evidence that alkaloids are key determinants of host plant use in these species. However, the results regarding the artificial novel host suggest that the effects of alkaloids on performance are not straightforward as D. koepferae was heavily affected. We discuss these results in the light of patterns of host plan evolution in the Drosophila repleta group. PMID:24520377

  6. [Pyrrolizidine alkaloids and seneciosis in farm animals. Part 1: occurrence, chemistry and toxicology].

    Science.gov (United States)

    Petzinger, E

    2011-01-01

    Pyrrolizidine alkaloids belong to a class of phytotoxins which are present in more than 6000 plant species. The disease seneciosis in farm animals represents the severe poisoning by pyrrolizidine alkaloids from plants of the genus Senecio. This form of poisoning has been known since the end of the 19th century in Germany, the USA, Canada and New Zealand, and is mainly caused by Senecio jacobaea and related Senecio spp. in farm animals, including poultry. Animal poisoning by pyrrolizidine alkaloids is of worldwide importance. In Germany poisoning of horses and cattle by Senecio jacobaea, which was earlier named Schweinsberg disease, is of renewed relevance for veterinary medicine. The disease occurs almost entirely as a consequence of chronic poisoning and in general ends fatally. The ultimate cause is the formation of toxic metabolites of pyrrolizidine alkaloids in the liver, and their covalent binding to nucleic acids and proteins leading to liver cirrhosis. Because many pyrrolizidine alkaloids possess mutagenic, and a few also carcinogenic properties, European and international authorities are concerned about possible residue levels in food of animal origin. The review addresses in its first part several aspects, being the occurrence, the chemistry, and the toxicology of pyrrolizidine alkaloids as well as animal intoxications by poisonous plants. In the second part (46) clinical characteristics of animal seneciosis, the therapeutic interventions, the significant species differences and a critical assessment of so-called nontoxic amounts of Senecio plants in animal fodder with reference to cumulative lethal toxin doses are presented.

  7. Budd-Chiari syndrome secondary to toxic pyrrolizidine alkaloid exposure.

    Science.gov (United States)

    Wu, Janet S W; Poon, W T; Ma, C K; Chen, M L; Pang, K S; Mak, Tony W L; Chan, H B

    2013-12-01

    In this report, we describe a case of pyrrolizidine alkaloid-related Budd-Chiari syndrome in Hong Kong. A 10-month-old boy presented with ascites, right pleural effusion, and hepatomegaly after consumption of herbal drinks for 3 months. His clinical (including imaging) features were compatible with Budd-Chiari syndrome. Budd-Chiari syndrome is a rare disease entity in paediatric patients. In our case, extensive workup performed to look for the underlying cause of Budd-Chiari syndrome was unrevealing, except for toxic pyrrolizidine alkaloid exposure in his herbal drinks.

  8. Semisynthetic dimers of antiparkinsonic ergot alkaloids

    Czech Academy of Sciences Publication Activity Database

    Křen, Vladimír; Weignerová, Lenka; Kuzma, Marek; Jegorov, A.; Sedmera, Petr

    2001-01-01

    Roč. 55, č. 6 (2001), s. 1045-1056 ISSN 0385-5414 R&D Projects: GA AV ČR IAA4020901 Institutional research plan: CEZ:AV0Z5020903 Keywords : ergot alkaloids * antiparkinsonic activity Subject RIV: EE - Microbiology, Virology Impact factor: 0.970, year: 2001

  9. Detection of Total Ergot Alkaloids in Cereal Flour and in Bread by a Generic Enzyme Immunoassay Method.

    Science.gov (United States)

    Gross, Madeleine; Curtui, Valeriu; Usleber, Ewald

    2018-05-01

    Four sets of polyclonal antibodies against ergot alkaloids ergometrine, ergotamine, α-ergocryptine, and ergocornine were produced and characterized in a competitive direct or indirect enzyme immunoassay (EIA). Standard curve LODs were 0.03 ng/mL (ergometrine EIA) to 2.0 ng/mL (ergocornine EIA). Three EIAs were highly specific, whereas the ergometrine EIA had a broad specificity pattern and reacted, albeit weakly, with all seven major ergot alkaloids and their epimeric forms. Using the ergometrine EIA, a generic test system was established in which total ergot alkaloids are quantified by a standard curve for a toxin mixture composed of three alkaloids that matched the ergot alkaloid composition in naturally contaminated rye and wheat products. Sample extraction with acetonitrile-phosphate-buffered saline at pH 6.0 without further cleanup was sufficient for EIA analysis. The LODs for total ergot alkaloids were 20 ng/g in rye and wheat flour and 14 ng/g in bread. Recoveries were 85-110% (RSDs of 0.1-11.7%) at a concentration range of 50-1000 ng/g. The total ergot alkaloid EIA was validated by comparison with HPLC-fluorescence detection. Although some under- and overestimation by the total ergot alkaloid EIA was observed, it was suitable for the reliable identification of positive samples at 10-20 ng/g and for the determination of total ergot alkaloids in a concentration range between 100 and 1000 ng/g.

  10. Toxicoproteomic assessment of liver responses to acute pyrrolizidine alkaloid intoxication in rats.

    Science.gov (United States)

    Li, Yan-Hong; Tai, William Chi-Shing; Khan, Imran; Lu, Cheng; Lu, Yao; Wong, Wing-Yan; Chan, Wood-Yee; Wendy Hsiao, Wen-Luan; Lin, Ge

    2018-04-03

    A toxicoproteomic study was performed on liver of rats treated with retrorsine (RTS), a representative hepatotoxic pyrrolizidine alkaloid at a toxic dose (140 mg/kg) known to cause severe acute hepatotoxicity. By comparing current data with our previous findings in mild liver lesions of rats treated with a lower dose of RTS, seven proteins and three toxicity pathways of vascular endothelial cell death, which was further verified by observed sinusoidal endothelial cell losses, were found uniquely associated with retrorsine-induced hepatotoxicity. This toxicoproteomic study of acute pyrrolizidine alkaloid intoxication lays a foundation for future investigation to delineate molecular mechanisms of pyrrolizidine alkaloid-induced hepatotoxicity.

  11. Towards a Molecular Understanding of the Biosynthesis of Amaryllidaceae Alkaloids in Support of Their Expanding Medical Use

    Directory of Open Access Journals (Sweden)

    Adam M. Takos

    2013-05-01

    Full Text Available The alkaloids characteristically produced by the subfamily Amaryllidoideae of the Amaryllidaceae, bulbous plant species that include well know genera such as Narcissus (daffodils and Galanthus (snowdrops, are a source of new pharmaceutical compounds. Presently, only the Amaryllidaceae alkaloid galanthamine, an acetylcholinesterase inhibitor used to treat symptoms of Alzheimer’s disease, is produced commercially as a drug from cultivated plants. However, several Amaryllidaceae alkaloids have shown great promise as anti-cancer drugs, but their further clinical development is restricted by their limited commercial availability. Amaryllidaceae species have a long history of cultivation and breeding as ornamental bulbs, and phytochemical research has focussed on the diversity in alkaloid content and composition. In contrast to the available pharmacological and phytochemical data, ecological, physiological and molecular aspects of the Amaryllidaceae and their alkaloids are much less explored and the identity of the alkaloid biosynthetic genes is presently unknown. An improved molecular understanding of Amaryllidaceae alkaloid biosynthesis would greatly benefit the rational design of breeding programs to produce cultivars optimised for the production of pharmaceutical compounds and enable biotechnology based approaches.

  12. Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae)

    Science.gov (United States)

    Introduction – The freshwater aquatic plant Gymnocoronis spilanthoides (Senegal tea plant, jazmín del bañado, Falscher Wasserfreund) is an invasive plant in many countries. Behavioural observations of pyrrolizidine alkaloid-pharmacophagous butterflies suggested the presence of pyrrolizidine alkaloid...

  13. [3H]PN200-110 and [3H]ryanodine binding and reconstitution of ion channel activity with skeletal muscle membranes

    International Nuclear Information System (INIS)

    Hamilton, S.L.; Alvarez, R.M.; Fill, M.; Hawkes, M.J.; Brush, K.L.; Schilling, W.P.; Stefani, E.

    1989-01-01

    Skeletal muscle membranes derived either from the tubular (T) network or from the sarcoplasmic reticulum (SR) were characterized with respect to the binding of the dihydropyridine, [ 3 H]PN200-110, and the alkaloid, [ 3 H]ryanodine; polypeptide composition; and ion channel activity. Conditions for optimizing the binding of these radioligands are discussed. A bilayer pulsing technique is described and is used to examine the channels present in these membranes. Fusion of T-tubule membranes into bilayers revealed the presence of chloride channels and dihydropyridine-sensitive calcium channels with three distinct conductances. The dihydropyridine-sensitive channels were further characterized with respect to their voltage dependence. Pulsing experiments indicated that two different populations of dihydropyridine-sensitive channels existed. Fusion of heavy SR vesicles revealed three different ion channels; the putative calcium release channel, a potassium channel, and a chloride channel. Thus, this fractionation procedure provides T-tubules and SR membranes which, with radioligand binding and single channel recording techniques, provide a useful tool to study the characteristics of skeletal muscle ion channels and their possible role in excitation-contraction coupling

  14. Aporphine and tetrahydroprotoberberine alkaloids from the leaves of Guatteria friesiana (Annonaceae) and their cytotoxic activities

    International Nuclear Information System (INIS)

    Costa, Emmanoel Vilaca; Cruz, Pedro Ernesto O. da; Marques, Francisco A.; Barison, Andersson; Maia, Beatriz Helena L.N.S.; Pinheiro, Maria Lucia B.; Ruiz, Ana Lucia T.G.; Marchetti, Gabriela M.; Carvalho, Joao Ernesto de

    2013-01-01

    Phytochemical investigation of the leaves of Guatteria friesiana (Annonaceae) afforded three new isoquinoline alkaloids, 13-hydroxy-discretinine, 6,6a-dehydroguatteriopsiscine and 9-dehydroxy-1-methoxy-dihydroguattouregidine. Eight known alkaloids were also isolated, 13-hydroxy-2,3,9,10-tetramethoxyprotoberberine, guatteriopsiscine, lysicamine, liriodenine, atherospermidine, lanuginosine, 7,8-dihydro-8-hydroxypalmatine and palmatine. 13-Hydroxy- 2,3,9,10-tetramethoxyprotoberberine was only obtained by synthesis and is being reported as a natural product for the first time. The structures of the isolated alkaloids were established by extensive analysis of 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometric (MS) data, as well as by comparison with data reported in the literature. The in vitro cytotoxic activity of the major alkaloids was evaluated against tumor and non-tumor cell lines. All of the alkaloids evaluated were determined to be inactive based on National Cancer Institute (NCI/USA) criteria. However, the alkaloid palmatine exhibited a cytostatic effect on MCF-7 (breast) and U251 (glioma) human tumor cell lines, with GI 50 values lower than 20.0 μmol L - 1 (10.5and 16.2μmolL -1 , respectively), suggesting a selective cytotoxic action (author)

  15. Rethinking of the criteria for natural analogue study. A case of Tono natural analogue study

    International Nuclear Information System (INIS)

    Yoshida, Hidekazu

    1996-01-01

    Natural analogue regarding long-term performance of the geological disposal system for radioactive waste isolation is essentially the study of geochemical process which has been evolved in geological environment. All geochemical studies, however, will not be nominated as natural analogue studies. It is, therefore, important to be clear the criteria for natural analogue study with the view of analogy by following three categories, (1) Conceptual model development, (2) Data provision and (3) Model testing, for the concept of geological disposal and safety assessment model. Rethinking of the criteria for natural analogue study through the case of Tono Natural Analogue Study, and the usefulness of natural analogue study for the safety assessment of geological disposal system in Japan have been presented in this paper. (author)

  16. POISONING OF CHICKENS AND DUCKS BY PYRROLIZIDINE ALKALOIDS OF HELIOTROPIUM EUROPAEUM.

    Science.gov (United States)

    Pass, D A; Hogg, G G; Russell, R G; Edgar, J A; Tence, I M; Rikard-Bell, L

    1979-05-01

    The disease produced by feeding chickens and ducks a commercial poultry feed containing heliotrine and lasiocarpine, pyrrolizidine alkaloids of Heliotropium europaeum, is described. Illthrift, ascites and degenerative lesions in the liver were the major findings. Similar lesions occurred in chickens fed a diet containing H. europaeum. The source of the alkaloids in commercial poultry feed was probably the seeds of H. europaeum harvested with wheat.

  17. Renieramycins H and I, two novel alkaloids from the sponge Haliclona cribricutis Dendy

    Digital Repository Service at National Institute of Oceanography (India)

    Parameswaran, P.S.; Naik, C.G.; Kamat, S.Y.; Pramanik, B.N.

    The known alkaloid, mimosamycin 1, along with its moon- and di hydroxy derivaties, 4-hydroxy mimosamycin 2 and 1, 4-dihydroxymimosamycin 3 and two new dimeric alkaloids: namely renieramycins H and I 4 and 5 have been isolated from the MeOH extract...

  18. Induced skeletal mutations

    International Nuclear Information System (INIS)

    Selby, P.B.

    1979-01-01

    This paper describes a large-scale experiment that, by means of breeding tests, confirmed that many dominant skeletal mutations are induced by large-dose radiation exposure. The author also discusses: (1) the major advantages and disadvantages of the skeletal method in improving estimates of genetic hazard to man; (2) future uses of the skeletal method; (3) direct estimation of risk beyond the first generation using the skeletal method; and (4) the possibility of using the skeletal method as a quick and easy screen for chemical mutagens

  19. Blood pyrrole-protein adducts as a diagnostic and prognostic index in pyrrolizidine alkaloid-hepatic sinusoidal obstruction syndrome.

    Science.gov (United States)

    Gao, Hong; Ruan, Jianqing Q; Chen, Jie; Li, Na; Ke, Changqiang Q; Ye, Yang; Lin, Ge; Wang, Jiyao Y

    2015-01-01

    The diagnosis of hepatic sinusoidal obstruction syndrome (HSOS) induced by pyrrolizidine alkaloids is mainly based on clinical investigation. There is currently no prognostic index. This study evaluated the quantitative measurement of blood pyrrole-protein adducts (PPAs) as a diagnostic and prognostic index for pyrrolizidine alkaloid-induced HSOS. Suspected drug-induced liver injury patients were prospectively recruited. Blood PPAs were quantitatively measured using ultra-performance liquid chromatography-tandem mass spectrometry. Patients' age, sex, biochemistry test results, and a detailed drug history were recorded. The patients were divided into two groups, ie, those with HSOS induced by pyrrolizidine alkaloid-containing drugs and those with liver injury induced by drugs without pyrrolizidine alkaloids. The relationship between herb administration, clinical outcomes, blood sampling time, and blood PPA concentration in pyrrolizidine alkaloid-associated HSOS patients was analyzed using multiple linear regression analysis. Forty patients met the entry criteria, among whom 23 had pyrrolizidine alkaloid-associated HSOS and 17 had liver injury caused by drugs without pyrrolizidine alkaloids. Among the 23 patients with pyrrolizidine alkaloid-associated HSOS, ten recovered, four developed chronic disease, eight died, and one underwent liver transplantation within 6 months after onset. Blood PPAs were detectable in 24 of 40 patients with concentrations from 0.05 to 74.4 nM. Sensitivity and specificity of the test for diagnosis of pyrrolizidine alkaloid-associated HSOS were 100% (23/23) and 94.1% (23/24), respectively. The positive predictive value was 95.8% and the negative predictive value was 100%, whereas the positive likelihood ratio was 23.81. The level of blood PPAs in the severe group (died or received liver transplantation) was significantly higher than that in the recovery/chronicity group (P=0.004). Blood PPAs measured by ultra-performance liquid

  20. Smart Nacre-inspired Nanocomposites.

    Science.gov (United States)

    Peng, Jingsong; Cheng, Qunfeng

    2018-03-15

    Nacre-inspired nanocomposites with excellent mechanical properties have achieved remarkable attention in the past decades. The high performance of nacre-inspired nanocomposites is a good basis for the further application of smart devices. Recently, some smart nanocomposites inspired by nacre have demonstrated good mechanical properties as well as effective and stable stimuli-responsive functions. In this Concept, we summarize the recent development of smart nacre-inspired nanocomposites, including 1D fibers, 2D films and 3D bulk nanocomposites, in response to temperature, moisture, light, strain, and so on. We show that diverse smart nanocomposites could be designed by combining various conventional fabrication methods of nacre-inspired nanocomposites with responsive building blocks and interface interactions. The nacre-inspired strategy is versatile for different kinds of smart nanocomposites in extensive applications, such as strain sensors, displays, artificial muscles, robotics, and so on, and may act as an effective roadmap for designing smart nanocomposites in the future. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  1. Repellence and attraction of Apis mellifera foragers by nectar alkaloids

    Directory of Open Access Journals (Sweden)

    Hroncová Z.

    2016-03-01

    Full Text Available Plant secondary metabolites present naturally in nectar, such as alkaloids, may change the behavioural responses of floral visitors and affect pollination. Some studies have shown that nectar containing low concentrations of these secondary metabolites is preferred by honey bee foragers over pure nectar. However, it remains unclear whether this is caused by dependence or addictive behaviour, a simple taste preference, or by other conditions such as self-medication. In our choice experiment, free-flying bees were presented with artificial flowers holding 20% sucrose containing 0.5−50 μg ml−1 of one of the naturally occurring nectar alkaloids - caffeine, nicotine, senecionine, and gelsemine. Nectar uptake was determined by weighing each flower and comparing the weight to that of the control flower. Our experimental design minimized memorizing and marking; despite this, caffeine was significantly preferred at concentrations 0.5−2 μg ml−1 over control nectar; this preference was not observed for other alkaloids. All of the compounds tested were repellent at concentrations above 5 μg ml−1. We confirmed previous reports that bees exhibit a preference for caffeine, and hypothesize that this is not due only to addictive behaviour but is at least partially mediated by taste preference. We observed no significant preference for nicotine or any other alkaloid.

  2. Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis.

    Science.gov (United States)

    da Silva Negreiros Neto, Themístocles; Gardner, Dale; Hallwass, Fernando; Leite, Ana Jéssica Matias; de Almeida, Camila Guimarães; Silva, Laura Nunes; de Araújo Roque, Alan; de Bitencourt, Fernanda Gobbi; Barbosa, Euzébio Guimarães; Tasca, Tiana; Macedo, Alexandre José; de Almeida, Mauro Vieira; Giordani, Raquel Brandt

    2016-10-01

    Crotalaria genus belongs to the subfamily Papilionoideae comprising about 600 species spread throughout tropical, neotropical and subtropical regions. In this study, seeds of Crolatalaria pallida were used to the isolation of usaramine, a pyrrolizidine alkaloid. Thus, Pseudomonas aeruginosa and Staphylococcus epidermidis were utilized as strains to test some activities of this alkaloid, such as antibiofilm and antibacterial. Meanwhile, monocrotaline obtained from Crotalaria retusa seeds, was used as the starting material for synthesis of necine base derivatives with anti-Trichomonas vaginalis potential. Alkaloids were characterized by 1D and 2D NMR techniques and GC-MS analysis. Usaramine demonstrated a highlighted antibiofilm activity against S. epidermidis by reducing more than 50% of biofilm formation without killing the bacteria, thus it could be assumed as a prototype for the development of new antibiofilm molecules for pharmaceutical and industrial purposes. Monocrotaline activity against T. vaginalis was evaluated and results indicated inhibition of 80% on parasite growth at 1mg/mL, in addition, neither cytotoxicity against vaginal epithelial cells nor hemolytic activity were observed. On the other hand, retronecine showed no anti-T. vaginalis activity while azido-retronecine was more active than monocrotaline killing 85% of the parasites at 1mg/mL. In conclusion, pyrrolizidine alkaloids are suggested as promising prototypes for new drugs especially for topical use. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

  3. Plant-symbiotic fungi as chemical engineers: multi-genome analysis of the clavicipitaceae reveals dynamics of alkaloid loci.

    Directory of Open Access Journals (Sweden)

    Christopher L Schardl

    Full Text Available The fungal family Clavicipitaceae includes plant symbionts and parasites that produce several psychoactive and bioprotective alkaloids. The family includes grass symbionts in the epichloae clade (Epichloë and Neotyphodium species, which are extraordinarily diverse both in their host interactions and in their alkaloid profiles. Epichloae produce alkaloids of four distinct classes, all of which deter insects, and some-including the infamous ergot alkaloids-have potent effects on mammals. The exceptional chemotypic diversity of the epichloae may relate to their broad range of host interactions, whereby some are pathogenic and contagious, others are mutualistic and vertically transmitted (seed-borne, and still others vary in pathogenic or mutualistic behavior. We profiled the alkaloids and sequenced the genomes of 10 epichloae, three ergot fungi (Claviceps species, a morning-glory symbiont (Periglandula ipomoeae, and a bamboo pathogen (Aciculosporium take, and compared the gene clusters for four classes of alkaloids. Results indicated a strong tendency for alkaloid loci to have conserved cores that specify the skeleton structures and peripheral genes that determine chemical variations that are known to affect their pharmacological specificities. Generally, gene locations in cluster peripheries positioned them near to transposon-derived, AT-rich repeat blocks, which were probably involved in gene losses, duplications, and neofunctionalizations. The alkaloid loci in the epichloae had unusual structures riddled with large, complex, and dynamic repeat blocks. This feature was not reflective of overall differences in repeat contents in the genomes, nor was it characteristic of most other specialized metabolism loci. The organization and dynamics of alkaloid loci and abundant repeat blocks in the epichloae suggested that these fungi are under selection for alkaloid diversification. We suggest that such selection is related to the variable life histories

  4. Alkaloids from Boophone haemanthoides (Amaryllidaceae)

    Czech Academy of Sciences Publication Activity Database

    Nair, J. J.; Rárová, L.; Strnad, Miroslav; Bastida, J.; van Staden, J.

    2013-01-01

    Roč. 8, č. 12 (2013), s. 1705-1710 ISSN 1934-578X Institutional research plan: CEZ:AV0Z50380511 Keywords : Alkaloid * Amaryllidaceae * Boophone haemanthoides Subject RIV: CE - Biochemistry Impact factor: 0.924, year: 2013 http://gateway.isiknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=Alerting&SrcApp=Alerting&DestApp=CCC&DestLinkType=FullRecord&UT=000328588200011

  5. Oxidative stress and production of bioactive monoterpene indole alkaloids: biotechnological implications.

    Science.gov (United States)

    Matsuura, Hélio Nitta; Rau, Mariana Ritter; Fett-Neto, Arthur Germano

    2014-02-01

    Monoterpene indole alkaloids (MIAs) encompass plant natural products with important pharmacological relevance. They include the anti-tumoral MIAs found in Catharanthus roseus and Camptotheca acuminata. The often low yields of bioactive alkaloids in plants has prompted research to identify the factors regulating MIA production. Oxidative stress is a general response associated with biotic and abiotic stresses leading to several secondary responses, including elicitation of MIA production. These changes in secondary metabolism may take place directly or via second messengers, such as Ca(2+) and reactive oxygen species (ROS). H2O2 is the main ROS that participates in MIA biosynthesis. This review analyzes the links between oxidative stress, elicitation of bioactive MIA production and their potential roles in antioxidant defense, as well as exploring the implications to developing biotechnological strategies relevant for alkaloid supply.

  6. Variation in the expression of ergot alkaloids between individual tillers of perennial ryegrass

    Science.gov (United States)

    Mace, Wade; Lunn, Kristy; Lloyd-West, Catherine

    2014-11-01

    Epichloë fungal endophytes of cool season grasses are well known to produce a range of alkaloids of benefit to the host. Some of these compounds are advantageous to agriculture due to qualities that promote pasture persistence (e.g. the loline class of alkaloids confer insect protection) while others are detrimental to the wellbeing of grazing livestock. The ergot alkaloids (e.g. ergovaline), produced in ryegrass and tall fescue associations, causes poor animal health in farming regions in many countries around the world and further study is required to improve our knowledge on this class of compounds. Here we present the application of a quantitative LC-MS/MS (liquid chromatography coupled to mass spectrometry) method measuring eight ergot alkaloids (chanoclavine, agroclavine, elymoclavine, lysergol, lysergic acid, ergine, lysergyl alanine, ergovaline) produced by endophyte infected grasses, to monitor levels in individual tillers from multiple plants of a single cultivar of perennial ryegrass (Lolium perenne cv. ‘Grasslands Samson’) infected with a common toxic endophyte strain (Epichloë festucae var. lolii). Monitoring the expression in individual tillers allows an estimation of the variability within a plant (between tillers) as well as between plants. The study showed that there is significant variation in the concentration of the ergot alkaloids between tillers of a single plant, at or exceeding the level of variation observed between individual plants of a population. This result emphasizes the fundamental importance of robust experimental design and sampling procedures when alkaloid expression assessment is required and these need to be rigorously tailored to the hypothesis being tested.

  7. Variation in the expression of ergot alkaloids between individual tillers of perennial ryegrass

    Directory of Open Access Journals (Sweden)

    Wade Jeffray Mace

    2014-11-01

    Full Text Available Epichloë fungal endophytes of cool season grasses are well known to produce a range of alkaloids of benefit to the host. Some of these compounds are advantageous to agriculture due to qualities that promote pasture persistence (e.g. the loline class of alkaloids confer insect protection while others are detrimental to the wellbeing of grazing livestock. The ergot alkaloids (e.g. ergovaline, produced in ryegrass and tall fescue associations, causes poor animal health in farming regions in many countries around the world and further study is required to improve our knowledge on this class of compounds. Here we present the application of a quantitative LC-MS/MS (liquid chromatography coupled to mass spectrometry method measuring eight ergot alkaloids (chanoclavine, agroclavine, elymoclavine, lysergol, lysergic acid, ergine, lysergyl alanine, ergovaline produced by endophyte infected grasses, to monitor levels in individual tillers from multiple plants of a single cultivar of perennial ryegrass (Lolium perenne cv. ‘Grasslands Samson’ infected with a common toxic endophyte strain (Epichloë festucae var. lolii. Monitoring the expression in individual tillers allows an estimation of the variability within a plant (between tillers as well as between plants.The study showed that there is significant variation in the concentration of the ergot alkaloids between tillers of a single plant, at or exceeding the level of variation observed between individual plants of a population. This result emphasizes the fundamental importance of robust experimental design and sampling procedures when alkaloid expression assessment is required and these need to be rigorously tailored to the hypothesis being tested.

  8. Independent Recruitment of a Flavin-Dependent Monooxygenase for Safe Accumulation of Sequestered Pyrrolizidine Alkaloids in Grasshoppers and Moths

    OpenAIRE

    Wang, Linzhu; Beuerle, Till; Timbilla, James; Ober, Dietrich

    2012-01-01

    Several insect lineages have developed diverse strategies to sequester toxic pyrrolizidine alkaloids from food-plants for their own defense. Here, we show that in two highly divergent insect taxa, the hemimetabolous grasshoppers and the holometabolous butterflies, an almost identical strategy evolved independently for safe accumulation of pyrrolizidine alkaloids. This strategy involves a pyrrolizidine alkaloid N-oxygenase that transfers the pyrrolizidine alkaloids to their respective N-oxide,...

  9. Isolation of alkaloid stachydrin from capparis spinosa L. and her new derivatives

    International Nuclear Information System (INIS)

    Nurmaganbetov, Zh.S.; Turmukhambetov, A.Zh.; Kazantsev, A.V.; Serperov, K.S.

    2005-01-01

    Phirrolidine alkaloid stachydrin was isolated from capparis spinosa L. New chemical derivatives of this new alkaloid were synthesized by reactions of halogenation (with bromine) and by reactions with methyl iodine and hydrochloric acid. The structures and composition of obtained compounds were determined on the basis of IR, 1 H NMR spectral data and elemental analysis

  10. Biosynthesis of ergot alkaloids from penicillium commune using response surface methodology (RSM)

    International Nuclear Information System (INIS)

    Shahid, M. G.; Cheema, T. A.; Baig, S.; Nadeem, M.; Nelofar, R.

    2017-01-01

    The present study employed the response surface methodology (RSM), a statistical technique, for the identification, screening and optimization of fermentation factors to produce ergot alkaloids under laboratory conditions by Penicillium commune. The static surface culture fermentation technique helped to enhance the production of ergot alkaloids. In the first step Plackett-Burman design (PBD) was used to evaluate the effect of ten factors, including nine ingredients of fermentation medium and one process parameter. It was found that sucrose, yeast extract and FeSO/sub 4/.7H/sub 2/O played the pivotal role in enhancing the yield of ergot alkaloids. In the second step, the effect of concentration levels of sucrose, yeast extract and FeSO/sub 4/.7H/sub 2/O was further optimized using Box-Behnken design (BBD) under the same fermentation conditions. The optimized concentrations of sucrose, yeast extract and FeSO/sub 4/.7H/sub 2/O were 41%, 39% and 0.11% respectively, which significantly enhanced the yield of ergot alkaloids. (author)

  11. Copper catalysed synthesis of indolylquinazolinone alkaloid ...

    Indian Academy of Sciences (India)

    ful reactions using copper catalyst have been reported in literature.9. The reported methods6 for the synthesis of bouchar- datine were reported, either via harsher reactions con- dition or multi-step sequence. Therefore, we are inter- ested in identifying mild reaction conditions for the construction of quinazolinone alkaloids.

  12. Butyrylcholinesterase, lipoxygenase inhibiting and antifungal alkaloids from Isatis tinctoria.

    Science.gov (United States)

    Ahmad, Ijaz; Fatima, Itrat

    2008-06-01

    Phytochemical investigations on the alkaloidal fraction of the whole plant of the Isatis tinctoria led to the isolation of the alkaloids 1-6. Compounds 3, 2 were found to be potent butyrylcholinesterase and lipoxygenase enzymes inhibitors in a concentration-dependent manner with the IC(50) values 16.3 +/- 0.06 and 19.7 +/- 0.03 microM against BChE and 30.6 +/- 0.02 and 33.7 +/- 0.05 microM against LOX, respectively. The compounds (1-6) showed significant antifungal activity against Trichophyton schoen leinii, Aspergillus niger, Candida albicans, Trichophyton simii, and Macrophomina phaseolina.

  13. Urease and serine protease inhibitory alkaloids from Isatis tinctoria.

    Science.gov (United States)

    Ahmad, Ijaz; Fatima, Itrat; Afza, Nighat; Malik, Abdul; Lodhi, Muhammad Arif; Choudhary, Muhammad Iqbal

    2008-12-01

    Phytochemical investigations on the alkaloidal fraction of the whole plant of the Isatis tinctoria led to the isolation of the alkaloids 1-6., 3'-Hydroxyepiglucoisatisin (3), Epiglucoisatisin (2) were found to be potent urease inhibitors in a concentration-dependent manner with IC(50) values 25.63 +/- 0.74, 37.01 +/- 0.41 and 31.72 +/- 0.93, 47.33 +/- 0.31 microM against Bacillus pasteurii & Jack bean urease, respectively. Compounds 3 and 2 also showed potent inhibitory potential against alpha-chymotrypsin with IC(50) values of 23.40 +/- 0.21 and 27.45 +/- 0.23 microM, respectively.

  14. Glutarimide alkaloids and a terpenoid benzoquinone from Cordia globifera.

    Science.gov (United States)

    Parks, Joshua; Gyeltshen, Thinley; Prachyawarakorn, Vilailak; Mahidol, Chulabhorn; Ruchirawat, Somsak; Kittakoop, Prasat

    2010-05-28

    Three new compounds, a meroterpene (2) having a cyclopropane moiety named globiferane and glutarimide alkaloids named cordiarimides A (3) and B (4), were isolated from the roots of Cordia globifera. Compounds 2-4 exhibited weak cytotoxic activity. Cordiarimide B (4) exhibited radical scavenging activity, as it inhibited superoxide anion radical formation in the xanthine/xanthine oxidase (XXO) assay, and also suppressed superoxide anion generation in differentiated HL-60 human promyelocytic leukemia cells when induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). This is the first report on the presence of glutarimide alkaloids in the genus Cordia.

  15. Alkaloid-derived molecules in low rank Argonne premium coals.

    Energy Technology Data Exchange (ETDEWEB)

    Winans, R. E.; Tomczyk, N. A.; Hunt, J. E.

    2000-11-30

    Molecules that are probably derived from alkaloids have been found in the extracts of the subbituminous and lignite Argonne Premium Coals. High resolution mass spectrometry (HRMS) and liquid chromatography mass spectrometry (LCMS) have been used to characterize pyridine and supercritical extracts. The supercritical extraction used an approach that has been successful for extracting alkaloids from natural products. The first indication that there might be these natural products in coals was the large number of molecules found containing multiple nitrogen and oxygen heteroatoms. These molecules are much less abundant in bituminous coals and absent in the higher rank coals.

  16. Antioxidant Potential of Cyclopeptyide Alkaloids Isolated from Zizyphus Oxphylla

    International Nuclear Information System (INIS)

    Kaleem, W.A.; Muhammad, N.; Khan, H.; Rauf, A.; Haq, M.Z.U.; Qayum, M.; Khan, A.Z.; Nisar, M.; Obaidullah, M.

    2015-01-01

    The present study reports on the antioxidant potential of five cyclopeptide alkaloids isolated from Zizyphus oxyphylla including Oxyphylline-D 1, Nummularin-C 2, Nummularin-R 3, Oxyphylline-B 4, Oxyphylline C 5 using DPPH free radical assay, nitric oxide radical assay and reducing power assay. The isolated alkaloids demonstrated marked antioxidant potential in a concentration dependent manner. Among the tested molecules, the compounds, 2 was most potent with IC50 values of 27.23, 32.03 and 22.45 μg/ml in DPPH free radical assay, nitric oxide radical assay and reducing power assay respectively. (author)

  17. [Analysis of effect of topographical conditions on content of total alkaloid in Coptidis Rhizoma in Chongqin, China].

    Science.gov (United States)

    Liu, Xin; Huang, He; Yang, Yan-fang; Wu, He-zhen

    2014-12-01

    To study ecology suitability rank dividing of the total alkaloid content of Coptis Rhizoma for selecting artificial planting base and high-quality industrial raw material in Chongqing province. Based on the investigation of PCB and DEM data of Chongqing province, the relationship between the total alkaloid content in Coptis Rhizoma and topographical conditions was analyzed by statistical analysis. The geographic information systems (GIS)-based assessment and landscape ecological principles were applied to assess eco logy suitability areas of Coptis Rhizoma in Chongqing. slope, aspect and altitude are main topographical factors that affect the content of the total alkaloid content in Coptis Rhizoma The total alkaloid content in Coptis Rhizoma is higher in the lower altitude, shady slope and bigger slope areas. The total alkaloid content is higher in the south areas of Chongqing province and lower in the northeast. Terrain conditions of the southern region of Chongqing are most suitable for The accumulated of total alkaloid Coptis Rhizoma content.

  18. Aporphine and tetrahydroprotoberberine alkaloids from the leaves of Guatteria friesiana (Annonaceae) and their cytotoxic activities

    Energy Technology Data Exchange (ETDEWEB)

    Costa, Emmanoel Vilaca; Cruz, Pedro Ernesto O. da, E-mail: emmanoelvc@gmail.com [Universidade Federal de Sergipe (UFSE), Sao Cristovao, SE (Brazil). Departamento de Quimica; Marques, Francisco A.; Barison, Andersson; Maia, Beatriz Helena L.N.S. [Universidade Federal do Parana (UFPR), Curitiba, PR (Brazil). Centro Politecnico. Departamento de Quimica; Pinheiro, Maria Lucia B. [Universidade Federal do Amazonas (UFAM), Manaus, AM (Brazil). Departamento de Quimica; Ruiz, Ana Lucia T.G.; Marchetti, Gabriela M.; Carvalho, Joao Ernesto de [Universidade Estadual de Campinas (UNICAMP), SP (Brazil). Centro Pluridisciplinar de Pesquisas Quimicas, Biologicas e Agricolas. Divisao de Farmacologia e Toxicologia

    2013-05-15

    Phytochemical investigation of the leaves of Guatteria friesiana (Annonaceae) afforded three new isoquinoline alkaloids, 13-hydroxy-discretinine, 6,6a-dehydroguatteriopsiscine and 9-dehydroxy-1-methoxy-dihydroguattouregidine. Eight known alkaloids were also isolated, 13-hydroxy-2,3,9,10-tetramethoxyprotoberberine, guatteriopsiscine, lysicamine, liriodenine, atherospermidine, lanuginosine, 7,8-dihydro-8-hydroxypalmatine and palmatine. 13-Hydroxy- 2,3,9,10-tetramethoxyprotoberberine was only obtained by synthesis and is being reported as a natural product for the first time. The structures of the isolated alkaloids were established by extensive analysis of 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometric (MS) data, as well as by comparison with data reported in the literature. The in vitro cytotoxic activity of the major alkaloids was evaluated against tumor and non-tumor cell lines. All of the alkaloids evaluated were determined to be inactive based on National Cancer Institute (NCI/USA) criteria. However, the alkaloid palmatine exhibited a cytostatic effect on MCF-7 (breast) and U251 (glioma) human tumor cell lines, with GI{sub 50} values lower than 20.0 Greek-Small-Letter-Mu mol L{sup -}1 (10.5and 16.2 Greek-Small-Letter-Mu molL{sup -1}, respectively), suggesting a selective cytotoxic action (author)

  19. Defensive properties of pyrrolizidine alkaloids against microorganisms

    NARCIS (Netherlands)

    Joosten, L.; Van Veen, J.A.

    2011-01-01

    The understanding of the selection factors that drive chemical diversification of secondary metabolites of constitutive defence systems in plants, such as pyrrolizidine alkaloids (PAs), is still incomplete. Historically, plants always have been confronted with microorganisms. Long before herbivores

  20. Alkaloid profile, antibacterial and allelopathic activities of Lupinus jaimehintoniana B.L. Turner (Fabaceae

    Directory of Open Access Journals (Sweden)

    Ruiz-González Nancy

    2012-01-01

    Full Text Available Herein we describe some aspects of the ethnobotanical use and the first alkaloid profile of Lupinus jaimehintoniana, the 5 to 8 m high arboreous lupine. Five quinolizidine alkaloids identified as sparteine, 5,6-dehydrolupanine, lupanine, nuttalline, and d-thermopsine, were characterized by the respective elution order according to their electronic impact spectra, lupanine being the most abundant in the four different tissues analyzed. Simultaneously, an antibacterial assessment of the four corresponding crude methanolic extracts, as well as the four semi-purified alkaloids was performed on specific Escherichia coli and Agrobacterium tumefaciens strains. These experiments resulted in MIC ranges of 37-61 µg mL-1 and 130-146 µg mL-1, respectively. for both bacterial species. Finally, the allelopathic activity of these extracts on the germination of Lactuca sativa seeds was demonstrated to be in the range of 50-300 µg mL-1 for both semi-purified alkaloid and methanolic extracts.

  1. Seeding-inspired chemotaxis genetic algorithm for the inference of biological systems.

    Science.gov (United States)

    Wu, Shinq-Jen; Wu, Cheng-Tao

    2014-09-18

    A large challenge in the post-genomic era is to obtain the quantitatively dynamic interactive information of the important constitutes of underlying systems. The S-system is a dynamic and structurally rich model that determines the net strength of interactions between genes and/or proteins. Good generation characteristics without the need for prior information have allowed S-systems to become one of the most promising canonical models. Various evolutionary computation technologies have recently been developed for the identification of system parameters and skeletal-network structures. However, the gaps between the truncated and preserved terms remain too small. Additionally, current research methods fail to identify the structures of high dimensional systems (e.g., 30 genes with 1800 connections). Optimization technologies should converge fast and have the ability to adaptively adjust the search. In this study, we propose a seeding-inspired chemotaxis genetic algorithm (SCGA) that can force evolution to adjust the population movement to identify a favorable location. The seeding-inspired training strategy is a method to achieve optimal results with limited resources. SCGA introduces seeding-inspired genetic operations to allow a population to possess competitive power (exploitation and exploration) and a winner-chemotaxis-induced population migration to force a population to repeatedly tumble away from an attractor and swim toward another attractor. SCGA was tested on several canonical biological systems. SCGA not only learned the correct structure within only one to three pruning steps but also ensures pruning safety. The values of the truncated terms were all smaller than 10 -14 , even for a thirty-gene system. Copyright © 2014 Elsevier Ltd. All rights reserved.

  2. Alkaloids of root barks of Zanthoxylum spp

    International Nuclear Information System (INIS)

    Hohlemwerger, Sandra Virginia Alves; Sales, Edijane Matos; Costa, Rafael dos Santos; Velozo, Eudes da Silva; Guedes, Maria Lenise da Silva

    2012-01-01

    In 1959, Gottlieb and Antonaccio published a study reporting the occurrence of lignan sesamin and triterpene lupeol in Zanthoxylum tingoassuiba. In this work we describe the phytochemical study of the root bark of the Z. tingoassuiba which allowed the identification of the lupeol, sesamin, and alkaloids dihydrochelerythrine, chelerythrine, anorttianamide, cis-N-methyl-canadin, predicentine, 2, 3-methylenedioxy-10,11-dimethoxy-tetrahydro protoberberine. The investigation of hexane and methanol extracts of the root bark of Z. rhoifolium and Z. stelligerum also investigated showed the presence of alkaloids dihydrochelerythrine, anorttianamide, cis-N-methyl-canadine, 7,9-dimethoxy-2,3- methylenedioxybenzophen anthridine and angoline. The occurrence of 2,3-methylenedioxy-10,11-dimethoxy-tetrahydro protoberberine is first described in Z. tingoassuiba and Z. stelligerum. This is also the first report of the presence of hesperidin and neohesperidin in roots of Z. stelligerum (author)

  3. CEC natural analogue working group

    International Nuclear Information System (INIS)

    Come, B.; Chapman, N.A.

    1986-01-01

    The second meeting of the CEC Natural Analogue Working Group took place on June 17-19, 1986, hosted by the Swiss NAGRA in Interlaken (CH). A review of recent progress in natural analogue programmes was carried out, and complemented by detailed discussions about geomicrobiology, archaeological analogues, natural colloids, and use of analogues to increase confidence in safety assessments for radioactive waste disposal. A statement drafted by the Group, and the presentations made, are put together in this report

  4. Acetylcholinesterase inhibitory activity of lycopodane-type alkaloids from the Icelandic Lycopodium annotinum ssp. alpestre

    DEFF Research Database (Denmark)

    Halldórsdóttir, Elsa Steinunn; Jaroszewski, Jerzy W; Olafsdottir, Elin Soffia

    2010-01-01

    The aim of this study was to investigate structures and acetylcholinesterase inhibitory activities of lycopodane-type alkaloids isolated from an Icelandic collection of Lycopodium annotinum ssp. alpestre. Ten alkaloids were isolated, including annotinine, annotine, lycodoline, lycoposerramine M...

  5. Five new indole alkaloids from the leaves of Rauvolfia yunnanensis.

    Science.gov (United States)

    Geng, Chang-An; Liu, Xi-Kui

    2013-09-01

    Five new indole alkaloids, rauvoloids A-E (1-5), together with two known ones, raucaffrinoline (6) and perakine (7) were isolated from the leaves of Rauvolfia yunnanensis. Their structures were elucidated by extensive spectroscopic methods. Structurally, rauvoloids A (1), B-C (2-3) and D (4) with unusual substitution patterns (no substitution, Cl and (1E)-3-oxo-butenyl, respectively) at C-20, are the first examples of perakine-type alkaloids with C18 and C22 skeletons. Copyright © 2013 Elsevier B.V. All rights reserved.

  6. New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures

    International Nuclear Information System (INIS)

    Tahchy, A. E.; Boisbrun, M.; Chretien, F.; Henry, M.; Chapleur, Y.; Laurain-Mattar, D.; Ptak, A.; Dupire, F.

    2010-01-01

    Biotransformation of deuterated-4'-O-methylnorbelladine into alkaloids galanthamine and lycorine in tissue cultures of Leucojum aestivum was demonstrated using HPLC coupled to mass spectrometry. GC-MS screening was also carried to investigate other native and deuterated alkaloids. A total of six labeled alkaloids were identified indicating that 4'-O-methyl-d3-norbelladine is incorporated into three different groups of Amaryllidaceae alkaloids that are biosynthesized by three modes of intramolecular oxidative phenol coupling. (authors)

  7. Cyclopeptide alkaloids. Synthesis of the ring system and its ion affinity

    International Nuclear Information System (INIS)

    Lagarias, J.C.; Houghten, R.A.; Rapoport, H.

    1978-01-01

    Several examples of the 14-membered, para-bridged ring system of the cyclopeptide alkaloids have been synthesized via an active ester cyclization. The yield of monomeric cyclopeptide varied from 1 to 33% and was affected by the amino acid substitution pattern and amide conformation of the linear peptide precursors. Both the synthetic models and a naturally occurring cyclopeptide alkaloid, ceanothine B, bind monovalent (Li + ) and divalent (Ca 2+ , Mg 2+ ) cations. 4 figures, 1 table

  8. Phosphorylated Derivatives of Alkaloids and Nitrogen-containing Heterocycles — Cholinesterase Inhibitors

    Science.gov (United States)

    Sadykov, Abid S.; Dalimov, D. N.; Godovikov, Nikolai N.

    1983-10-01

    The review deals with the synthesis and anticholinesterase activities of phosphorylated derivatives of certain alkaloids and nitrogen-containing heterocycles. It is shown that the conformational properties of the alkaloid and nitrogen-containing heterocycle residues in the composition of the organophosphorus inhibitor (OPI) molecule play an important role in the inhibition of the catalytic activity of cholinesterases. The type of inhibition of cholinesterases also varies as a function of chemical structure. The bibliography includes 45 references.

  9. Extractions of isoquinoline alkaloids with butanol and octanol.

    Science.gov (United States)

    Gregorová, Jana; Babica, Jan; Marek, Radek; Paulová, Hana; Táborská, Eva; Dostál, Jirí

    2010-09-01

    Six different isoquinoline alkaloids (sanguinarine, chelerythrine, berberine, coptisine, allocryptopine, and protopine) were extracted by butanol and octanol from aqueous solution, pH 4.5. The samples were analyzed by HPLC. Butanol extraction was non-selective, alkaloids passed into organic phase in 83-98%. Octanol extraction provided more selective yields: sanguinarine 99%, chelerythrine 94%, berberine 18%, coptisine 16%, allocryptopine 7.5%, protopine 7%. Further, we tested octanol treatment of extract from Dicranostigma lactucoides. The octanol extraction yields were also selective: sanguinarine 98%, chelerythrine 92%, chelirubine 92.5%, protopine 6% and allocryptopine 3.5%. 6-Butoxy-5,6-dihydrosanguinarine and 6-butoxy-5,6-dihydrochelerythrine were prepared and their NMR and MS data are reported and discussed. Copyright (c) 2010 Elsevier B.V. All rights reserved.

  10. Protective Effects of Alkaloid Compounds from Nelumbinis Plumula on tert-Butyl Hydroperoxide-Induced Oxidative Stress

    Directory of Open Access Journals (Sweden)

    Ze-Bin Guo

    2013-08-01

    Full Text Available This study was conducted to investigate the effect of Nelumbinis Plumula total alkaloid (NPA and its main alkaloid components on oxidative stress induced by tert-butyl hydroperoxide (t-BHP in the human hepatocellular HepG2 cell line. According to HPLC analysis, several major alkaloid compounds such as liensinine, isoliensinine and neferine were present in NPA. The cytotoxic effects in 0.55 mM t-BHP-induced HepG2 cells were significantly inhibited by NPA and the major compound in NPA, neferine, showed the strongest activities. The protective effect of neferine against oxidative stress induced by t-BHP may be associated with decreased ROS formation, TBARS generation, LDH release and increased GSH levels, suggesting their involvement of the cytoprotective on oxidative stress. The effects were comparable with quercetin, which was used as positive control. Overall, total alkaloid and alkaloid compounds from Nelumbinis Plumula displayed a significant cytoprotective effect against oxidative stress. Further study is needed to elucidate the relationship between the chemical structures of the components in NPA and their protective effect on oxidative stress.

  11. Crotalaria medicaginea associated with horse deaths in northern Australia: new pyrrolizidine alkaloids.

    Science.gov (United States)

    Fletcher, Mary T; Hayes, Patricia Y; Somerville, Michael J; De Voss, James J

    2011-11-09

    Crotalaria medicaginea has been implicated in horse poisoning in grazing regions of central-west Queensland, which resulted in the deaths of more than 35 horses from hepatotoxicosis in 2010. Liver pathology was suggestive of pyrrolizidine alkaloidosis, and we report here the isolation of two previously uncharacterized pyrrolizidine alkaloids from C. medicaginea plant specimens collected from pastures where the horses died. The first alkaloid was shown by mass spectometric and NMR analyses to be 1β,2β-epoxy-7β-hydroxy-1α-methoxymethyl-8α-pyrrolizidine, which, like other alkaloids previously isolated from C. medicaginea, lacks the requisite functionality for hepatotoxcity. The second alkaloid isolated in this investigation was a new macrocyclic diester of otonecine, which we have named cromedine. The (1)H and (13)C NMR spectra of cromedine were fully assigned by 2D NMR techniques and allowed the constitution of the macrocyclic diester to be assigned unambiguously. C. medicaginea specimens implicated in this investigation do not belong to any of the three recognized Australian varieties (C. medicaginea var. neglecta, C. medicaginea var. medicaginea, and C. medicaginea var. linearis) and appear to be a local variant or form, referred to here as C. medicaginea (chemotype cromedine).

  12. Workers and alate queens of Solenopsis geminata share qualitatively similar but quantitatively different venom alkaloid chemistry

    Directory of Open Access Journals (Sweden)

    Qun-Hui eShi

    2015-07-01

    Full Text Available Solenopsis geminata group (Hymenoptera: Formicidae encompasses ant species commonly called fire ants because of their painful sting. The many physiological effects of the venom are caused by 2-methyl-6-alkyl and/or alkenylpiperidine alkaloids. The variation in piperidine alkaloid structures has useful taxonomic characters. The most well studied Solenopsis species is S. invicta, which was accidentally imported into the USA in the 1930s from South America. It quickly spread throughout the southern USA and is now a major invasive pest ant in the USA and in other parts of the world. Interestingly, the invasive S. invicta has largely displaced a native USA fire ant, S. geminata, from the southern USA. We explore the possibility that differences in venom chemistry could be correlated with this displacement. The cis and trans alkaloids from body extracts of workers and alate queens of S. geminata were separated by silica gel chromatography, identified, and quantitated by GC-MS analysis. Both workers and alate queens produce primarily cis- and trans-2-methyl-6-n-undecyl-piperidines, as well as other minor alkaloid components. Imported fire ant, S. invicta, alate queens produce the same alkaloids as S. geminata alate queens, but in contrast S. invicta workers produce piperidine alkaloids with longer side chains, which are purported to be physiologically more effective. These results are discussed in relation to the evolutionary progression of fire ant venom alkaloids and displacement of S. geminata by S. invicta in the USA.

  13. [Study on the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia].

    Science.gov (United States)

    Bozhadze, A D; Vachnadze, V Iu; Dzhokhadze, M S; Berashvili, D T; Bakuridze, A Dzh

    2013-04-01

    In present article was studied the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia. Alkaloids were extracted from medicinal herbal material and separated by liquid extraction, diluents gas and a microfiltration through membrane equipment. The obtained A1, A2, A3 fractions were analyzed by GC/MS method; in all cases separation proceeds by the principle of extraction of the target alkaloids. It was concluded that the A1 is enriched with α and β cryptopins, and protopin, but homochelidonine and chelidonine are in low contents. As accompanying alkaloid is identified dihydrosanguinarine as an artifact; the A2 is enriched with the maximum contents of stylopine and protopin, but the poor contents of chelidonine and homochelidonine; the A3 is enriched with α and β cryptopins and maximum content of chelidonine. Extraction of alkaloids from Chelidonium majus L. proceeds selectively, but depending on a way of separation of the total alkaloids allows varying qualitative and quantitative consistence of the final product.

  14. Sensitive determination of pyrrolizidine alkaloids in Tussilago farfara L. by field-amplified, sample-stacking, sweeping micellar electrokinetic chromatography.

    Science.gov (United States)

    Cao, Kun; Xu, Yi; Mu, Xiuni; Zhang, Qing; Wang, Renjie; Lv, Junjiang

    2016-11-01

    Pyrrolizidine alkaloids are the toxic components in Tussilago farfara L. Due to the lack of standard substances for quantitative analysis and traces of pyrrolizidine alkaloids in total alkaloids, the full quality control of Tussilago farfara L has been limited. In this study, we aimed to solve the difficulty of determination of pyrrolizidine alkaloids and identify more components in the total alkaloids. An on-line preconcentration method has been applied to improve determining sensitivity of pyrrolizidine alkaloids in Tussilago farfara L. in which included field-amplified sample stacking and sweeping in micellar electrokinetic capillary chromatography. The main parameters that affected separation and stacking efficiency were investigated in details. Under the optimal conditions, the sensitivity enhancement factors obtained by the developed method for the analytes were from 15- to 12-fold, the limits of detection of senkirkine and senecionine were 2∼5 μg/L. Senkirkine and senecionine have been detected in alkaloids (c) of Tussilago farfara L, along ferulic acid methyl ester and methyl caffeate. The developed method was also applied to the analysis of acid extraction (a) of Tussilago farfara L, and senkirkine could be detected directly. The results indicated that the developed method is feasible for the analysis of pyrrolizidine alkaloids in Tussilago farfara L with good recoveries. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  15. Study on synthesis and properties of nanoparticles loaded with amaryllidaceous alkaloids

    Directory of Open Access Journals (Sweden)

    Duan Lihong

    2017-11-01

    Full Text Available Alzheimer’s disease (AD is the most common disease among the elderly people and a major social and medical problem. Amaryllidaceous alkaloids, acting as acetylcholinesterase inhibitors, represent a potential treatment of AD. However, they also have some deficiencies, such as extensive toxicity and widespread side effects. In order to improve the bioavailability and reduce the toxic and side effects, brain targeting of amaryllidaceous alkaloids was enhanced by considering low density lipoprotein (LDL receptors of blood-brain barrier (BBB endothelial cells as therapeutic targets. Amaryllidaceous alkaloids were highly selectively and quantitatively riveted to the surface of low density lipoproteins by using a new method - mild click chemistry. The structure of products has been characterized by NMR, FT-IR, and other methods. In addition, drug loading rate, encapsulation rate, and drug release by the nanoparticles were determined to assess the quality of the nanoparticles.

  16. Determination of tropane alkaloids by heart cutting reversed phase - Strong cation exchange two dimensional liquid chromatography.

    Science.gov (United States)

    Long, Zhen; Zhang, Yanhai; Gamache, Paul; Guo, Zhimou; Steiner, Frank; Du, Nana; Liu, Xiaoda; Jin, Yan; Liu, Xingguo; Liu, Lvye

    2018-01-01

    Current Chinese Pharmacopoeia (ChP) standards apply liquid extraction combined with one dimensional liquid chromatography (1DLC) method for determining alkaloids in herbal medicines. The complex pretreatments lead to a low analytical efficiency and possible component loss. In this study, a heart cutting reversed phase - strong cation exchange two dimensional liquid chromatography (RP - SCX 2DLC) approach was optimized for simultaneously quantifying tropane alkaloids (anisodine, scopolamine and hyoscyamine) in herbal medicines and herbal medicine tablets without further treatment of the filtered extract. The chromatographic conditions were systematically optimized in terms of column type, mobile phase composition and flow rate. To improve peak capacity and obtain symmetric peak shape of alkaloids, a polar group embedded C18 column combined with chaotropic salts was used in the first dimension. To remove the disturbance of non-alkaloids, achieve unique selectivity and acquire symmetric peak shape of alkaloids, an SCX column combined with phosphate buffer was used in the second dimension. Method validation was performed in terms of linearity, precision (0.54-0.82%), recovery (94.1-105.2%), limit of detection (LOD) and limit of quantification (LOQ) of the three analytes varied between 0.067-0.115mgL -1 and 0.195-0.268mgL -1 , respectively. The method demonstrated superiority over 1DLC method in respect of resolution (less alkaloid co-eluted), sample preparation (no pretreatment procedure) and transfer rate (minimum component loss). The optimized RP - SCX 2DLC approach was subsequently applied to quantify target alkaloids in five herbal medicines and herbal medicine tablets from three different manufactures. The results demonstrated that the developed heart cutting RP - SCX 2DLC approach represented a new, strategically significant methodology for the quality evaluation of tropane alkaloid in related herbal medicines that involve complex chemical matrix. Copyright

  17. Patterns of indole alkaloids synthesis in response to heat shock, 5-azacytidine and Na-butyrate treatment of cultured catharanthus roseus mesophyll protoplasts

    International Nuclear Information System (INIS)

    Saleem, M.; Cutler, A.J.

    1986-01-01

    Alkaloids of C. roseus are in high demand for therapeutic and other reasons. Cultured Catharanthus cells can produce limited quantities of these alkaloids. The authors have found that cultured mesophyll protoplasts in the presence of 14 C-Tryptamine are capable of synthesizing alkaloids. The pattern of alkaloids synthesis changes when protoplasts are subjected to a heat shock at 37 0 C. The heat shocked protoplasts incorporated 33% more 14 C-Tryptamine and produced 3 new types of alkaloids. Treatment of protoplasts with 5-azacytidine, a DNA hypomethylating agent and Na-butyrate which induces hyperacetylation of histones produced qualitative and quantitative changes in the alkaloid pattern. Four new alkaloids following the above treatments were detected by TLC and HPLC of the extracts. It is suggested that the alkaloid pattern of the cultured protoplasts can be altered by treatment with compounds known as regulators of gene expression. Work is in progress to isolate and identify these new alkaloids

  18. Physicists get INSPIREd

    CERN Multimedia

    CERN Bulletin

    2010-01-01

    Particle physicists thrive on information. They first create information by performing experiments or elaborating theoretical conjectures and then they share it through publications and various web tools. The INSPIRE service, just released, will bring state of the art information retrieval to the fingertips of researchers.   Keeping track of the information shared within the particle physics community has long been the task of libraries at the larger labs, such as CERN, DESY, Fermilab and SLAC, as well as the focus of indispensible services like arXiv and those of the Particle Data Group. In 2007, many providers of information in the field came together for a summit at SLAC to see how physics information resources could be enhanced, and the INSPIRE project emerged from that meeting. The vision behind INSPIRE was built by a survey launched by the four labs to evaluate the real needs of the community. INSPIRE responds to these directives from the community by combining the most successful aspe...

  19. Bio-inspired networking

    CERN Document Server

    Câmara, Daniel

    2015-01-01

    Bio-inspired techniques are based on principles, or models, of biological systems. In general, natural systems present remarkable capabilities of resilience and adaptability. In this book, we explore how bio-inspired methods can solve different problems linked to computer networks. Future networks are expected to be autonomous, scalable and adaptive. During millions of years of evolution, nature has developed a number of different systems that present these and other characteristics required for the next generation networks. Indeed, a series of bio-inspired methods have been successfully used to solve the most diverse problems linked to computer networks. This book presents some of these techniques from a theoretical and practical point of view. Discusses the key concepts of bio-inspired networking to aid you in finding efficient networking solutions Delivers examples of techniques both in theoretical concepts and practical applications Helps you apply nature's dynamic resource and task management to your co...

  20. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids

    Digital Repository Service at National Institute of Oceanography (India)

    Al-Mourabit, A.; Zancanella, M.A.; Tilvi, S.; Romo, D.

    The pyrrole-2-aminoimidazole (P-2-AI) alkaloids are a growing family of marine alkaloids, now numbering well over 150 members, with high topographical and biological information content. Their intriguing structural complexity, rich and compact...

  1. Antitrichomonal activity of Peganum harmala alkaloid extract against trichomoniasis in pigeon (Columba livia domestica).

    Science.gov (United States)

    Tabari, M A; Youssefi, M R; Moghadamnia, A A

    2017-06-01

    1. This study was designed to evaluate the antitrichomonal effects of P. harmala alkaloid extract against T. gallinae, both in vitro and in vivo, as well as comparing it to that of metronidazole, conventional antitrichomonal medication and harmine and harmaline, the two alkaloids present in P. harmala. 2. T. gallinae were collected by the wet mount method from infected free-living pigeons. The in vitro assay was performed using multi-well plates containing test compounds in final concentrations of 5, 10, 15, 20, 30, 50 or 100 μg/ml. The in vivo assay was done on 60 experimentally infected pigeons dosed with metronidazole at 50 mg/kg body weight (BW) or alkaloids at 25 mg/kg BW. 3. The 24 h minimum inhibitory concentration (MIC) of alkaloid extract was 15 µg/ml while that of metronidazole was 50 µg/ml. Harmine and harmaline revealed 24 h MIC of 30 and 100 µg/ml, respectively. Treatment of infected pigeons with alkaloids led to a full recovery after 3 d but with metronidazole total eradication of trophozoites was not achieved. 4. In conclusion, data of the present study suggested P. harmala is a potent natural anti-trichomonal agent, effective against T. gallinae.

  2. Tandem Mass Spectrometry for Structural Identification of Sesquiterpene Alkaloids from the Stems of Dendrobium nobile Using LC-QToF.

    Science.gov (United States)

    Wang, Yan-Hong; Avula, Bharathi; Abe, Naohito; Wei, Feng; Wang, Mei; Ma, Shuang-Cheng; Ali, Zulfiqar; Elsohly, Mahmoud A; Khan, Ikhlas A

    2016-05-01

    Dendrobium nobile is one of the fundamental herbs in traditional Chinese medicine. Sesquiterpene alkaloids are the main active components in this plant. Due to weak ultraviolet absorption and low content in D. nobile, these sesquiterpene alkaloids have not been extensively studied using chromatographic methods. Herein, tandem mass spectrometry combined with liquid chromatography separation provides a tool for the identification and characterization of the alkaloids from D. nobile. A total of nine sesquiterpene alkaloids were characterized by ultrahigh-performance liquid chromatography tandem mass spectrometry. These alkaloids can be classified into two subgroups that are represented by dendrobine and nobilonine. Tandem mass spectrometric studies revealed the fragmentation pathways of these two subgroup alkaloids that were used for the identification and characterization of other alkaloids in D. nobile. Characterization of these alkaloids using accurate mass and diagnostic fragments provided a reliable methodology for the analysis of D. nobile by ultrahigh-performance liquid chromatography tandem mass spectrometry. The limit of detection was defined as the signal-to-noise ratio equal to 3 : 1. Limits of detection of dendrobine and nobilonine were less than 30 ng/mL. The developed method was applied for the analysis of various Dendrobium species and related dietary supplements. Alkaloids were identified from D. nobile, but not detected from commercial samples including 13 other Dendrobium species and the 7 dietary supplements. Georg Thieme Verlag KG Stuttgart · New York.

  3. Effects of tryptophan derivatives and β-carboline alkaloids on radiation- and peroxide-induced transformations of ethanol

    International Nuclear Information System (INIS)

    Sverdlov, R.L.; Brinkevich, S.D.; Shadyro, O.I.

    2014-01-01

    The subject of this study was investigation of interactions of tryptophan and its derivatives, including structurally related β-carboline alkaloids with oxygen- and carbon-centered radicals being formed during radiation- and peroxide-induced transformations of ethanol. It was shown that the above named compounds suppressed recombination and disproportionation reactions of α-hydroxyethyl radicals. The inhibitory effects of tryptophan, 5-hydroxytryptophan and serotonin were mainly realized by means of reduction and addition reactions, while those of β-carboline alkaloids – harmine, harmane and harmaline – were due to oxidation reactions. Melatonin displayed low reactivity towards α-hydroxyethyl radicals. Tryptophan derivatives and β-carboline alkaloids were found to inhibit radiation-induced oxidation of ethanol while being virtually not used up. The low transformation yields of tryptophan, 5-hydroxytryptophan and serotonin, as well as β-carboline alkaloids, indicate their capability of regeneration, which could occur on interaction of tryptophan with O ·− 2 and HO · 2 , or on oxidation of α-hydroxyethyl radicals by β-carboline alkaloids. - Highlights: • Tryptophan, 5-hydroxytryptophane and serotonin can reduce or add α-HER. • β-Carboline alkaloids – harmane, harmine, harmaline – can oxidize α-HER. • Tryptophan and its derivatives can reduce oxygen-centered radicals

  4. Metabolic activation of pyrrolizidine alkaloids leading to phototoxicity and photogenotoxicity in human HaCaT keratinocytes.

    Science.gov (United States)

    Wang, Chia-Chi; Xia, Qingsu; Li, Meng; Wang, Shuguang; Zhao, Yuewei; Tolleson, William H; Yin, Jun-Jie; Fu, Peter P

    2014-01-01

    Pyrrolizidine alkaloids, produced by a large number of poisonous plants with wide global distribution, are associated with genotoxicity, tumorigenicity, and hepatotoxicity in animals and humans. Mammalian metabolism converts pyrrolizidine alkaloids to reactive pyrrolic metabolites (dehydropyrrolizidine alkaloids) that form covalent protein and DNA adducts. Although a mechanistic understanding is currently unclear, pyrrolizidine alkaloids can cause secondary (hepatogenous) photosensitization and induce skin cancer. In this study, the phototoxicity of monocrotaline, riddelliine, dehydromonocrotaline, dehydroriddelliine, and dehydroretronecine (DHR) in human HaCaT keratinocytes under ultraviolet A (UVA) irradiation was determined. UVA irradiation of HaCaT cells treated with dehydromonocrotaline, dehydroriddelline, and DHR resulted in increased release of lactate dehydrogenase and enhanced photocytotoxicity proportional to the UVA doses. UVA-induced photochemical DNA damage also increased proportionally with dehydromonocrotaline and dehydroriddelline. UVA treatment potentiated the formation of 8-hydroxy-2'-deoxyguanosine DNA adducts induced by dehydromonocrotaline in HaCaT skin keratinocytes. Using electron spin resistance trapping, we found that UVA irradiation of dehydromonocrotaline and dehydroriddelliine generates reactive oxygen species (ROS), including hydroxyl radical, singlet oxygen, and superoxide, and electron transfer reactions, indicating that cytotoxicity and genotoxicity of these compounds could be mediated by ROS. Our results suggest that dehydropyrrolizidine alkaloids formed or delivered to the skin cause pyrrolizidine alkaloid-induced secondary photosensitization and possible skin cancer.

  5. Larvicidal and Nematicidal Activities of 3-Acylbarbituric Acid Analogues against Asian Tiger Mosquito, Aedes albopictus, and Pine Wood Nematode, Bursaphelenchus xylophilus

    Directory of Open Access Journals (Sweden)

    Seon-Mi Seo

    2017-07-01

    Full Text Available Widespread concern for the occurrence of resistant strains, along with the avoidance of the use of highly toxic insecticides and their wide environmental dispersal, highlights the need for the development of new and safer pest control agents. Natural products provide inspiration for new chemical entities with biological activities, and their analogues are good lead compounds for the development of new pest control agents. For this purpose, we evaluated the larvicidal and nematicidal activities of 48 3-acylbarbituric acid analogues against the Asian tiger mosquito, Aedes albopictus and the pine wood nematode, Bursaphelenchus xylophilus, organisms of increasing global concern. Among the 48 3-acylbarbituric acid analogues, four compounds—10, 14d, 14g and 19b—showed >90% larvicidal activity against Ae. albopictus at 10 μg/mL concentration, and one (compound 10 showed the strongest larvicidal activity against Ae. albopictus, with a LC50 value of 0.22 μg/mL. Only compound 18 showed strong nematicidal activity against pine wood nematode. Most active compounds possessed similar physicochemical properties; thus, actives typically had ClogP values of around 1.40–1.50 and rel-PSA values of 16–17% and these similar cheminformatic characteristics reflect their similar structure. This study indicates that active 3-acylbarbituric acids analogues have potential as lead compounds for developing novel mosquito control agents.

  6. CEC Natural Analogue Working Group

    International Nuclear Information System (INIS)

    Come, B.; Chapman, N.A.

    1989-01-01

    The central theme for the third meeting of the CEC analogue working group was ''How can analogue data be used for performance assessments, both in support of the results and for presentation to the public''. This report puts together the most recent achievements in this field, together with a review of on-going natural analogue programmes

  7. Antifatigue and increasing exercise performance of Actinidia arguta crude alkaloids in mice

    Directory of Open Access Journals (Sweden)

    Yangyang Liu

    2016-10-01

    Full Text Available Actinidia arguta (Siebold et Zucc. Planch. ex. Miq. is one of the most recently domesticated fruit species with increasing commercial production worldwide. It is a well-known traditional Chinese medicine and is used to reduce blood glucose and treat atopic dermatitis. In addition, it possesses antioxidant, anticancer, and antiallergic properties. In this study, we investigated the physical antifatigue and exercise performance effects of A. arguta crude alkaloids (AACA extracted with 70% ethanol. Four groups of male Kunming mice (n = 16 were orally administered AACA at doses of 0 mg/kg/d (vehicle, 50 mg/kg/d (AACA-50, 100 mg/kg/d (AACA-100, or 200 mg/kg/d (AACA-200 for 28 days. The effect of AACA treatment on exercise performance was studied using the forelimb grip strength experiment and by the measurement of the weight-loaded swimming time. The antifatigue effect is evaluated based on fatigue-associated biochemical parameters, hepatic and muscular glycogen levels, and changes in the morphology of transverse and longitudinal sections of skeletal muscle. The results showed that AACA could elevate the endurance and grip strength in mice. The exhaustive swimming time of the AACA-50, AACA-100, and AACA-200 groups was significantly (p < 0.05 increased compared with the vehicle. The swimming time of the AACA-100 group was the longest among all groups studied. Mice in the AACA-treated groups had decreased levels of lactate, ammonia, and creatine kinase after a physical challenge compared with the vehicle group. The tissue glycogen, an important energy source during exercise, significantly increased with AACA. The morphology of transverse and longitudinal sections of skeletal muscle did not change in the vehicle group. Overall, these findings suggest that AACA possesses antifatigue effects and increases exercise performance in mice. Therefore, A. arguta may be developed as an antifatigue dietary supplement in the category of functional foods.

  8. Single cell subtractive transcriptomics for identification of cell-specifically expressed candidate genes of pyrrolizidine alkaloid biosynthesis.

    Science.gov (United States)

    Sievert, Christian; Beuerle, Till; Hollmann, Julien; Ober, Dietrich

    2015-09-01

    Progress has recently been made in the elucidation of pathways of secondary metabolism. However, because of its diversity, genetic information concerning biosynthetic details is still missing for many natural products. This is also the case for the biosynthesis of pyrrolizidine alkaloids. To close this gap, we tested strategies using tissues that express this pathway in comparison to tissues in which this pathway is not expressed. As many pathways of secondary metabolism are known to be induced by jasmonates, the pyrrolizidine alkaloid-producing species Heliotropium indicum, Symphytum officinale, and Cynoglossum officinale of the Boraginales order were treated with methyl jasmonate. An effect on pyrrolizidine alkaloid levels and on transcript levels of homospermidine synthase, the first specific enzyme of pyrrolizidine alkaloid biosynthesis, was not detectable. Therefore, a method was developed by making use of the often observed cell-specific production of secondary compounds. H. indicum produces pyrrolizidine alkaloids exclusively in the shoot. Homospermidine synthase is expressed only in the cells of the lower leaf epidermis and the epidermis of the stem. Suggesting that the whole pathway of pyrrolizidine alkaloid biosynthesis might be localized in these cells, we have isolated single cells of the upper and lower epidermis by laser-capture microdissection. The resulting cDNA preparations have been used in a subtractive transcriptomic approach. Quantitative real-time polymerase chain reaction has shown that the resulting library is significantly enriched for homospermidine-synthase-coding transcripts providing a valuable source for the identification of further genes involved in pyrrolizidine alkaloid biosynthesis. Copyright © 2015 Elsevier Ltd. All rights reserved.

  9. The Difference Se Makes: A Bio-Inspired Dppf-Supported Nickel Selenolate Complex Boosts Dihydrogen Evolution with High Oxygen Tolerance.

    Science.gov (United States)

    Pan, Zhong-Hua; Tao, Yun-Wen; He, Quan-Feng; Wu, Qiao-Yu; Cheng, Li-Ping; Wei, Zhan-Hua; Wu, Ji-Huai; Lin, Jin-Qing; Sun, Di; Zhang, Qi-Chun; Tian, Dan; Luo, Geng-Geng

    2018-06-12

    Inspired by the metal active sites of [NiFeSe]-hydrogenases, a dppf-supported nickel(II) selenolate complex (dppf=1,1'-bis(diphenylphosphino)ferrocene) shows high catalytic activity for electrochemical proton reduction with a remarkable enzyme-like H 2 evolution turnover frequency (TOF) of 7838 s -1 under an Ar atmosphere, which markedly surpasses the activity of a dppf-supported nickel(II) thiolate analogue with a low TOF of 600 s -1 . A combined study of electrochemical experiments and DFT calculations shed light on the catalytic process, suggesting that selenium atom as a bio-inspired proton relay plays a key role in proton exchange and enhancing catalytic activity of H 2 production. For the first time, this type of Ni selenolate-containing electrocatalyst displays a high degree of O 2 and H 2 tolerance. Our results should encourage the development of the design of highly efficient oxygen-tolerant Ni selenolate molecular catalysts. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Retention behavior of selected alkaloids in Reversed Phase micellar chromatographic systems

    Directory of Open Access Journals (Sweden)

    Petruczynik Anna

    2015-06-01

    Full Text Available In this work, the effects of sodium dodecyl sulfate (SDS concentrations on retention, separation selectivity, peak shapes and systems efficiency were investigated. Herein, the retention data for 11 alkaloids were determined on an RP18 silica column with mobile phases containing methanol as organic modifier, with acetate buffer at pH 3.5, and, subsequently, with the addition of sodium dodecyl sulfate (SDS. The results of this study indicate that the retention of alkaloids decreases with the increase of SDS concentration in the mobile phase. The increase of SDS concentration, however, leads to the significantly improvement of peak symmetry and the increase of theoretical plate number in all cases. The best system efficiency for most of the investigated alkaloids was obtained in a mobile phase containing 0.1 M SDS, while most symmetrical peaks were obtained through the addition of 0.3 M of SDS to the mobile phase.

  11. Pyridine-type alkaloid composition affects bacterial community composition of floral nectar.

    Science.gov (United States)

    Aizenberg-Gershtein, Yana; Izhaki, Ido; Santhanam, Rakesh; Kumar, Pavan; Baldwin, Ian T; Halpern, Malka

    2015-06-30

    Pyridine-type alkaloids are most common in Nicotiana species. To study the effect of alkaloid composition on bacterial community composition in floral nectar, we compared the nicotine-rich wild type (WT) N. attenuata, the nicotine biosynthesis-silenced N. attenuata that was rich in anatabine and the anabasine-rich WT N. glauca plants. We found that the composition of these secondary metabolites in the floral nectar drastically affected the bacterial community richness, diversity and composition. Significant differences were found between the bacterial community compositions in the nectar of the three plants with a much greater species richness and diversity in the nectar from the transgenic plant. The highest community composition similarity index was detected between the two wild type plants. The different microbiome composition and diversity, caused by the different pyridine-type alkaloid composition, could modify the nutritional content of the nectar and consequently, may contribute to the change in the nectar consumption and visitation. These may indirectly have an effect on plant fitness.

  12. Cat's claw oxindole alkaloid isomerization induced by common extraction methods

    Directory of Open Access Journals (Sweden)

    Samuel Kaiser

    2013-01-01

    Full Text Available Cat's claw oxindole alkaloids are prone to isomerization in aqueous solution. However, studies on their behavior in extraction processes are scarce. This paper addressed the issue by considering five commonly used extraction processes. Unlike dynamic maceration (DM and ultrasound-assisted extraction, substantial isomerization was induced by static maceration, turbo-extraction and reflux extraction. After heating under reflux in DM, the kinetic order of isomerization was established and equations were fitted successfully using a four-parameter Weibull model (R² > 0.999. Different isomerization rates and equilibrium constants were verified, revealing a possible matrix effect on alkaloid isomerization.

  13. Anticancer and reversing multidrug resistance activities of natural isoquinoline alkaloids and their structure-activity relationship.

    Science.gov (United States)

    Qing, Zhi-Xing; Huang, Jia-Lu; Yang, Xue-Yi; Liu, Jing-Hong; Cao, Hua-Liang; Xiang, Feng; Cheng, Pi; Zeng, Jian-Guo

    2017-09-20

    The severe anticancer situation as well as the emergence of multidrug-resistant (MDR) cancer cells has created an urgent need for the development of novel anticancer drugs with different mechanisms of action. A large number of natural alkaloids, such as paclitaxel, vinblastine and camptothecin have already been successfully developed into chemotherapy agents. Following the success of these natural products, in this review, twenty-six types of isoquinoline alkaloid (a total of 379 alkaloids), including benzyltetrahydroisoquinoline, aporphine, oxoaporphine, isooxoaporphine, dimeric aporphine, bisbenzylisoquinoline, tetrahydroprotoberberine, protoberberine, protopine, dihydrobenzophenanthridine, benzophenanthridine, benzophenanthridine dimer, ipecac, simple isoquinoline, pavine, montanine, erythrina, chelidonine, tropoloisoquinoline, azafluoranthene, phthalideisoquinoline, naphthylisoquinoline, lycorine, crinane, narciclasine, and phenanthridone, were summarized based on their cytotoxic and MDR reversing activities against various cancer cells. Additionally, the structure-activity relationships of different types of isoquinoline alkaloid were also discussed. Interestingly, some aporphine, oxoaporphine, isooxoaporphine, bisbenzylisoquinoline, and protoberberine alkaloids display more potent anticancer activities or anti-MDR effects than positive control against the tested cancer cells and are regarded as attractive targets for discovery new anticancer drugs or lead compounds. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  14. A Submarine Journey: The Pyrrole-Imidazole Alkaloids

    Directory of Open Access Journals (Sweden)

    Alessandra Scolaro

    2009-11-01

    Full Text Available In his most celebrated tale “The Picture of Dorian Gray”, Oscar Wilde stated that “those who go beneath the surface do so at their peril”. This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity − from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products.

  15. Multiple shoot cultures of Atropa belladonna: Effect of physico-chemical factors on growth and alkaloid formation

    International Nuclear Information System (INIS)

    Benjamin, B.D.; Roja, P.C.; Heble, M.R.; Chandha, M.S.

    1987-01-01

    Multiple shoot cultures were established from shoot tip and axillary meristem of the plant Atropa belladonna. The cultures were initially raised on agar medium and subsequently maintained on liquid medium of Murashige and Skoog (1962) supplemented with BA. These cultures were subjected to different doses of -y-irradiation. Recovery from the radiation effects was observed in tissues subjected to 29 Gy during four successive passages. Plant growth regulators influenced the growth and morphogenetic events of the tissues. The precursors of tropane alkaloids marginally increased the alkaloid synthesis during the stationary phase of growth. Shoot cultures, established from different field grown plants varying in alkaloid content, were morphologically similar and did not exhibit the parental characteristics with respect to alkaloid formation

  16. The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom.

    Science.gov (United States)

    Hotti, Hannu; Rischer, Heiko

    2017-11-14

    Coniine, a polyketide-derived alkaloid, is poisonous to humans and animals. It is a nicotinic acetylcholine receptor antagonist, which leads to inhibition of the nervous system, eventually causing death by suffocation in mammals. Coniine's most famous victim is Socrates who was sentenced to death by poison chalice containing poison hemlock in 399 BC. In chemistry, coniine holds two historical records: It is the first alkaloid the chemical structure of which was established (in 1881), and that was chemically synthesized (in 1886). In plants, coniine and twelve closely related alkaloids are known from poison hemlock ( Conium maculatum L.), and several Sarracenia and Aloe species. Recent work confirmed its biosynthetic polyketide origin. Biosynthesis commences by carbon backbone formation from butyryl-CoA and two malonyl-CoA building blocks catalyzed by polyketide synthase. A transamination reaction incorporates nitrogen from l-alanine and non-enzymatic cyclization leads to γ-coniceine, the first hemlock alkaloid in the pathway. Ultimately, reduction of γ-coniceine to coniine is facilitated by NADPH-dependent γ-coniceine reductase. Although coniine is notorious for its toxicity, there is no consensus on its ecological roles, especially in the carnivorous pitcher plants where it occurs. Lately there has been renewed interest in coniine's medical uses particularly for pain relief without an addictive side effect.

  17. Pharmacological and Toxicological Profile of Harmane-β-Carboline Alkaloid: Friend or Foe.

    Science.gov (United States)

    Khan, Haroon; Patel, Seema; Kamal, Mohammad A

    2017-01-01

    The plant secondary metabolites have an outstanding therapeutic potential and success over the years. In fact, it is the foundation of numerous clinically used drugs. Similarly, these is a general perception that these products are inherent safety. However, such products might have toxic/unwanted lethal effects therefore, along with biological relevance, toxicological evaluation is equally important for clinical applications. Therefore, harmane- β-carboline alkaloid was investigated for both therapeutic and toxicological potential. The literature related to the therapeutic/toxicological effects of the alkaloid was searched using various scientific data bases including Google, ScienceDirect, PubMed, SpringerLink, ASC. The peer reviewed articles were only selected. The harmane-β-carboline alkaloid has shown several pharmacological activities such as antianxiety, antidepressant, antiplatelet, antidiabetic, acetylcholinesterase and myeloperoxidase inhibition, antioxidant, antiparasitic, hypotensive, morphine withdrawal syndrome alleviation, and antinociceptive effects. On the other hand, it exhibited tremorogenic effect, for a symptom of Parkinson's disease. Adverse effect of the alkaloid on learning and memory have also been observed. All together, it is, concluded in this review that harmane elicited marked pharmacological effects but simultaneously, it possessed some serious side effects that could be the primary hurdle in the way of its clinical testing. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  18. Analogue alternative the electronic analogue computer in Britain and the USA, 1930-1975

    CERN Document Server

    Small, James S

    2013-01-01

    We are in the midst of a digital revolution - until recently, the majority of appliances used in everyday life have been developed with analogue technology. Now, either at home or out and about, we are surrounded by digital technology such as digital 'film', audio systems, computers and telephones. From the late 1940s until the 1970s, analogue technology was a genuine alternative to digital, and the two competing technologies ran parallel with each other. During this period, a community of engineers, scientists, academics and businessmen continued to develop and promote the analogue computer.

  19. Inspiration from britain?

    DEFF Research Database (Denmark)

    Vagnby, Bo

    2008-01-01

    Danish housing policy needs a dose of renewed social concern - and could find new inspiration in Britain's housing and urban planning policies, says Bo Vagnby. Udgivelsesdato: November......Danish housing policy needs a dose of renewed social concern - and could find new inspiration in Britain's housing and urban planning policies, says Bo Vagnby. Udgivelsesdato: November...

  20. Two bromotyrosine alkaloids from the sponge Psammaplysilla purpurea

    Digital Repository Service at National Institute of Oceanography (India)

    Tilvi, S.; Parameswaran, P.S.; Naik, C.G.

    , antimicrobial properties etc. Herein is reported isolation and structure determination of two such alkaloids: 16-debromo aplysamine-4 1 and purpuramine 1 2 from the sponge @iP. purpurea@@ collected from Mandapam, Tamil Nadu, India. The structures...

  1. Tolerating Toxins: Grasshoppers that Feast on Pyrrolizidine Alkaloids §.

    Science.gov (United States)

    Housecroft, Catherine E

    2018-03-30

    The elegant grasshopper (Zonocerus elegans) and the variegated grasshopper (Z. variegatus) are among insects that deliberately consume and store pyrrolizidine alkaloids which are subsequently used in defence mechanisms.

  2. An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS.

    Science.gov (United States)

    Pan, Huiqin; Yang, Wenzhi; Zhang, Yibei; Yang, Min; Feng, Ruihong; Wu, Wanying; Guo, Dean

    2015-08-01

    The exploration of new chemical entities from herbal medicines may provide candidates for the in silico screening of drug leads. However, this significant work is hindered by the presence of multiple classes of plant metabolites and many re-discovered structures. This study presents an integrated strategy that uses ultrahigh-performance liquid chromatography/linear ion-trap quadrupole/Orbitrap mass spectrometry (UHPLC/LTQ-Orbitrap-MS) coupled with in-house library data for the systematic characterization and discovery of new potentially bioactive molecules. Exploration of the indole alkaloids from Uncaria rhynchophylla (UR) is presented as a model study. Initially, the primary characterization of alkaloids was achieved using mass defect filtering and neutral loss filtering. Subsequently, phytochemical isolation obtained 14 alkaloid compounds as reference standards, including a new one identified as 16,17-dihydro-O-demethylhirsuteine by NMR analyses. The direct-infusion fragmentation behaviors of these isolated alkaloids were studied to provide diagnostic structural information facilitating the rapid differentiation and characterization of four different alkaloid subtypes. Ultimately, after combining the experimental results with a survey of an in-house library containing 129 alkaloids isolated from the Uncaria genus, a total of 92 alkaloids (60 free alkaloids and 32 alkaloid O-glycosides) were identified or tentatively characterized, 56 of which are potential new alkaloids for the Uncaria genus. Hydroxylation on ring A, broad variations in the C-15 side chain, new N-oxides, and numerous O-glycosides, represent the novel features of the newly discovered indole alkaloid structures. These results greatly expand our knowledge of UR chemistry and are useful for the computational screening of potentially bioactive molecules from indole alkaloids. Graphical Abstract A four-step integrated strategy for the systematic characterization and efficient discovery of new indole

  3. Dihydro-β-agarofuran sesquiterpene pyridine alkaloids from the seeds of Euonymus hamiltonianus

    Directory of Open Access Journals (Sweden)

    Mudasir A. Tantry

    2016-09-01

    Full Text Available Plants of the Celastraceae family produce various dihydro-β-agarofuran sesquiterpene pyridine alkaloids. Two dihydro-β-agarofuran sesquitepene pyridine alkaloids (1,2 apart from four known compounds euojaponin C (3, wilforine (4, austronine (5 and O9-benzoyl-O9-deacetylevonine (6, were isolated from the ripe seeds of Euonymus hamiltonianus. Their chemical structures were elucidated mainly by analysis of NMR and MS spectral data. All compounds were evaluated for insecticidal activity.

  4. Extraction-spectrophotometric determination of purine alkaloids in water solutions using aliphatic alcohols

    Directory of Open Access Journals (Sweden)

    Y. I. Korenman

    2012-01-01

    Full Text Available For extraction of caffeine, theobromin and theophylline from water solutions are applied aliphatic alcohols С3 – С9. Water concentrates analyzed method UF- spectrophotometry. Factors of distribution and extraction degree are calculated. Influence of length of a hydrocarbonic radical in a solvent and nature olecule salting-out agent on interphase distribution of alkaloids is studied. Dependence of quantitative characteristics extraction from number active groups in structure alkaloids is established.

  5. Clustered Ergot Alkaloids Modulate Cell-mediated Cytotoxicity

    Czech Academy of Sciences Publication Activity Database

    Křen, Vladimír; Fišerová, Anna; Weignerová, Lenka; Stibor, I.; Halada, Petr; Přikrylová, Věra; Sedmera, Petr; Pospíšil, Miloslav

    2002-01-01

    Roč. 10, - (2002), s. 415-424 ISSN 0968-0896 R&D Projects: GA AV ČR IAA4020901; GA ČR GA310/98/0347 Institutional research plan: CEZ:AV0Z5020903 Keywords : clustered * ergot * alkaloids Subject RIV: EE - Microbiology, Virology Impact factor: 2.043, year: 2002

  6. New bisbenzylisoquinoline alkaloid from Laureliopsis philippiana

    DEFF Research Database (Denmark)

    Stærk, Dan; Thi, Loi Pham; Rasmussen, Hasse Bonde

    2009-01-01

    Phytochemical investigation of Laureliopsis philippiana resulted in isolation of a new bisbenzylisoquinoline alkaloid (1) named laureliopsine A. The structure was established by spectroscopic methods, including 2D homo- and heteronuclear NMR experiments. This finding of a bisbenzylisoquinoline al...

  7. Ergot alkaloid intoxication in perennial ryegrass (Lolium perenne): an emerging animal health concern in Ireland?

    Science.gov (United States)

    Canty, Mary J; Fogarty, Ursula; Sheridan, Michael K; Ensley, Steve M; Schrunk, Dwayne E; More, Simon J

    2014-01-01

    Four primary mycotoxicosis have been reported in livestock caused by fungal infections of grasses or cereals by members of the Clavicipitaceae family. Ergotism (generally associated with grasses, rye, triticale and other grains) and fescue toxicosis (associated with tall fescue grass, Festuca arundinacea) are both caused by ergot alkaloids, and referred to as 'ergot alkaloid intoxication'. Ryegrass staggers (associated with perennial ryegrass Lolium perenne) is due to intoxication with an indole-diperpene, Lolitrem B, and metabolites. Fescue-associated oedema, recently described in Australia, may be associated with a pyrrolizidine alkaloid, N-acetyl norloline. Ergotism, caused by the fungus Claviceps purpurea, is visible and infects the outside of the plant seed. Fescue toxicosis and ryegrass staggers are caused by Neotyphodium coenophalium and N. lolii, respectively. Fescue-associated oedema has been associated with tall fescue varieties infected with a specific strain of N. coenophialum (AR542, Max P or Max Q). The name Neotyphodium refers to asexual derivatives of Epichloë spp., which have collectively been termed the epichloë fungi. These fungi exist symbiotically within the grass and are invisible to the naked eye. The primary toxicological effect of ergot alkaloid involves vasoconstriction and/or hypoprolactinaemia. Ingestion of ergot alkaloid by livestock can cause a range of effects, including poor weight gain, reduced fertility, hyperthermia, convulsions, gangrene of the extremities, and death. To date there are no published reports, either internationally or nationally, reporting ergot alkaloid intoxication specifically associated with perennial ryegrass endophytes. However, unpublished reports from the Irish Equine Centre have identified a potential emerging problem of ergot alkaloid intoxication with respect to equines and bovines, on primarily perennial ryegrass-based diets. Ergovaline has been isolated in varying concentrations in the herbage of a

  8. The Actions of Piperidine Alkaloids at Fetal Muscle-Type and Autonomic-Type Nicotinic Acetylcholine Receptors

    Science.gov (United States)

    Piperidine alkaloids are found in many species of plants including Conium maculatum, Nicotiana spp., and Lupinus spp. A pharmacodynamic comparison was made of the alkaloids ammodendrine, anabasine, anabaseine, and coniine in; SH-SY5Y cells which express autonomic-type nicotinic acetylcholine recept...

  9. Genotoxic Pyrrolizidine Alkaloids — Mechanisms Leading to DNA Adduct Formation and Tumorigenicity

    OpenAIRE

    Ming W. Chou; Ge Lin; Qingsu Xia; Peter P. Fu

    2002-01-01

    Abstract: Plants that contain pyrrolizidine alkaloids are widely distributed in the world. Although pyrrolizidine alkaloids have been shown to be genotoxic and tumorigenic in experimental animals, the mechanisms of actions have not been fully understood. The results of our recent mechanistic studies suggest that pyrrolizidine alkaloids induce tumors via a genotoxic mechanism mediated by 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5Hpyrrolizine (DHP)-derived DNA adduct formation. This mechanism may ...

  10. Pyrrolizidine alkaloids in honey: comparison of analytical methods

    NARCIS (Netherlands)

    Kempf, M.; Wittig, M.; Reinhard, A.; Ohe, von der K.; Blacquière, T.; Raezke, K.P.; Michel, R.; Schreier, P.; Beuerle, T.

    2011-01-01

    Pyrrolizidine alkaloids (PAs) are a structurally diverse group of toxicologically relevant secondary plant metabolites. Currently, two analytical methods are used to determine PA content in honey. To achieve reasonably high sensitivity and selectivity, mass spectrometry detection is demanded. One

  11. DISTRIBUTION OF ALKALOIDS AND TANNINS IN THE CRASSULACEAE

    NARCIS (Netherlands)

    STEVENS, JF; THART, H; VANHAM, CHJ; ELEMA, ET; VANDENENT, MMVX; WILDEBOER, M; ZWAVING, JH

    Alkaloid and tannin levels of 36 species of the Crassulaceae were compared. The taxa investigated were Crassula multicava, Echeveria venezuelensis, Pachyphytum compactum, Kalanchoe (two sop.), Bryophyllum daigremontianum, Sedum (23 spp.), Aeonium (four spp.) and Sempervivum (three spp.). Apart from

  12. Sensing properties of pristine boron nitride nanostructures towards alkaloids: A first principles dispersion corrected study

    Science.gov (United States)

    Roondhe, Basant; Dabhi, Shweta D.; Jha, Prafulla K.

    2018-05-01

    To understand the underlying physics behind the interaction of biomolecules with the nanomaterials to use them practically as bio-nanomaterials is very crucial. A first principles calculation under the frame work of density functional theory is executed to investigate the electronic structures and binding properties of alkaloids (Caffeine and Nicotine) over single walled boron nitride nanotube (BNNT) and boron nitride nanoribbon (BNNR) to determine their suitability towards filtration or sensing of these molecules. We have also used GGA-PBE scheme with the inclusion of Van der Waals (vdW) interaction based on DFT-D2. Increase in the accuracy by incorporating the dispersion correction in the calculation is observed for the long range Van der Waals interaction. Binding energy range of BNNT and BNNR with both alkaloids have been found to be -0.35 to -0.76 eV and -0.45 to -0.91 eV respectively which together with the binding distance shows physisorption binding of these molecules to the both nanostructures. The transfer of charge between the BN nanostructures and the adsorbed molecule has also been analysed by using Lowdin charge analysis. The sensitivity of both nanostructures BNNT and BNNR towards both alkaloids is observed through electronic structure calculations, density of states and quantum conductance. The binding of both alkaloids with BNNR is stronger. The analysis of the calculated properties suggests absence of covalent interaction between the considered species (BNNT/BNNR) and alkaloids. The study may be useful in designing the boron nitride nanostructure based sensing device for alkaloids.

  13. Comparative study of fourteen alkaloids from Uncaria rhynchophylla hooks and leaves using HPLC-diode array detection-atmospheric pressure chemical ionization/MS method.

    Science.gov (United States)

    Qu, Jialin; Gong, Tianxing; Ma, Bin; Zhang, Lin; Kano, Yoshihiro; Yuan, Dan

    2012-01-01

    The purpose of the study is to compare alkaloid profile of Uncaria rhynchophylla hooks and leaves. Ten oxindole alkaloids and four glycosidic indole alkaloids were identified using HPLC-diode array detection (DAD) or LC-atmospheric pressure chemical ionization (APCI)-MS method, and a HPLC-UV method for simultaneous quantification of major alkaloids was validated. The hooks are characterized by high levels of four oxindole alkaloids rhynchophylline (R), isorhynchophylline (IR), corynoxeine (C) and isocorynoxeine (IC), while the leaves contained high level of two glycosidic indole alkaloids vincoside lactam (VL) and strictosidine (S). The presented methods have proven its usefulness in chemical characterization of U. rhynchophylla hooks and leaves.

  14. Complete inhibition of fetal movement in the day 40 pregnant goat model by the piperidine alkaloid anabasine but not related alkaloids

    Science.gov (United States)

    Four chemically similar alkaloids, anabasine, anabaseine, epibatidine and dimethylphenylpiperazinium (DMPP), are potent nicotinic acetylcholine receptor agonists of fetal muscle nicotinic acetylcholine receptors in human TE-671 cells. Based on results with these cells, we hypothesized that these alk...

  15. Riboflavin-mediated photosensitization of Vinca alkaloids distorts drug sensitivity assays.

    Science.gov (United States)

    Granzow, C; Kopun, M; Kröber, T

    1995-11-01

    Poor reproducibility of cytotoxicity tests with Vinca alkaloids has frequently been reported. A commonly presumed light sensitivity of the drugs could not be confirmed. However, we found that they are photosensitized by riboflavin (vitamin B2), an obligatory component of cell culture media. Light of wavelengths below 500 nm triggered rapid photoreactions of riboflavin with vinblastine, vincristine, and vindesine in aqueous solutions. The photoreactions altered the absorption spectra of these alkaloids and yielded degradation products that could be separated by TLC. In cell cultures, both immediate and persisting, riboflavin-mediated photoreactivity could be distinguished. They preclude reliable determinations of sensitivity and resistance to Vinca alkaloids, as exemplified on chemosensitive and multidrug-resistant mouse ascites cells. In experiments involving photosensitization, the 50% inhibitory concentration values of sensitive and resistant cells were overlapping and fluctuated in the ranges from 3 to 30 nM and 15 to 360 nM vinblastine, respectively. Corresponding values from series of experiments protected from photosensitization were 1.02 +/- 0.22 nM and 18.5 +/- 3.42 nM. Hence, riboflavin-mediated photoreactions must be fully prevented in assays of cellular drug sensitivity. Procedures for eliminating immediate as well as persisting photoreactivity were established.

  16. The chemistry of isoindole natural products

    OpenAIRE

    Speck, Klaus; Magauer, Thomas

    2013-01-01

    Summary This review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton. This motif is found in its intact or modified form in indolocarbazoles, macrocyclic polyketides (cytochalasan alkaloids), the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloids. Concerning their biological activity, molecular structure and synthesis, we have limited this review to the most inspiring examples...

  17. Livestock Poisoning with Pyrrolizidine Alkaloid Containing Plants (Senecio, Crotalaria, Cynoglossum, Amsinckia, Heliotropium and Echium spp.)

    Science.gov (United States)

    Pyrrolizidine alkaloids (PAs) are potent liver toxins that have been identified in over 6,000 plants throughout the world. Alkaloids are nitrogen-based compounds with potent biological activity. About half of the identified PAs are toxic and several cause cancer (carcinogenic). PA-containing plants...

  18. Natural Analogue Synthesis Report

    Energy Technology Data Exchange (ETDEWEB)

    A. M. Simmons

    2002-05-01

    The purpose of this report is to present analogue studies and literature reviews designed to provide qualitative and quantitative information to test and provide added confidence in process models abstracted for performance assessment (PA) and model predictions pertinent to PA. This report provides updates to studies presented in the ''Yucca Mountain Site Description'' (CRWMS M and O 2000 [151945], Section 13) and new examples gleaned from the literature, along with results of quantitative studies conducted specifically for the Yucca Mountain Site Characterization Project (YMP). The intent of the natural analogue studies was to collect corroborative evidence from analogues to demonstrate additional understanding of processes expected to occur during postclosure at a potential Yucca Mountain repository. The report focuses on key processes by providing observations and analyses of natural and anthropogenic (human-induced) systems to improve understanding and confidence in the operation of these processes under conditions similar to those that could occur in a nuclear waste repository. The process models include those that represent both engineered and natural barrier processes. A second purpose of this report is to document the various applications of natural analogues to geologic repository programs, focusing primarily on the way analogues have been used by the YMP. This report is limited to providing support for PA in a confirmatory manner and to providing corroborative inputs for process modeling activities. Section 1.7 discusses additional limitations of this report. Key topics for this report are analogues to emplacement drift degradation, waste form degradation, waste package degradation, degradation of other materials proposed for the engineered barrier, seepage into drifts, radionuclide flow and transport in the unsaturated zone (UZ), analogues to coupled thermal-hydrologic-mechanical-chemical processes, saturated zone (SZ) transport

  19. NATURAL ANALOGUE SYNTHESIS REPORT

    International Nuclear Information System (INIS)

    Simmons, A.M.

    2004-01-01

    The purpose of this report is to present analogue studies and literature reviews designed to provide qualitative and quantitative information to test and provide added confidence in process models abstracted for performance assessment (PA) and model predictions pertinent to PA. This report provides updates to studies presented in the Yucca Mountain Site Description (CRWMS M and O 2000 [151945], Section 13) and new examples gleaned from the literature along with results of quantitative studies conducted specifically for the Yucca Mountain Project (YMP). The intent of the natural analogue studies was to collect corroborative evidence from analogues to demonstrate additional understanding of processes expected to occur during postclosure at a potential Yucca Mountain repository. The report focuses on key processes by providing observations and analyses of natural and anthropogenic (human-induced) systems to improve understanding and confidence in the operation of these processes under conditions similar to those that could occur in a nuclear waste repository. The process models include those that represent both engineered and natural barrier processes. A second purpose of this report is to document the various applications of natural analogues to geologic repository programs, focusing primarily on the way analogues have been used by the YMP. This report is limited to providing support for PA in a confirmatory manner and to providing corroborative inputs for process modeling activities. Section 1.7 discusses additional limitations of this report. Key topics for this report are analogues to emplacement-drift degradation, waste-form degradation, waste-package degradation, degradation of other materials proposed for the engineered barrier, seepage into drifts, radionuclide flow and transport in the unsaturated zone (UZ), analogues to coupled thermal-hydrologic-mechanical-chemical processes, saturated-zone (SZ) transport, impact of radionuclide release on the biosphere

  20. Alkaloids as chemotaxonomic markers from the Philippine endemic Uncaria perrottetii and Uncaria lanosa f. philippinensis

    Directory of Open Access Journals (Sweden)

    Jay Edneil Olivar

    2018-04-01

    Full Text Available Phytochemical investigation on the aerial parts of Uncaria perrottetii led to the isolation of three pentacyclic oxindole alkaloids uncarine A or isoformosanine (1, uncarine E or isopteropodine (2, and rauniticine-allo-oxindole A (3. Five oxindole alkaloids, isomitraphylline (4, mitraphylline (5, uncarine B or formosanine (6, uncarine F (7, corynoxine (8, and uncarine D or speciophylline (9, were isolated from the leaves of Uncaria lanosa f. philippinensis. Their structures were determined by spectroscopic techniques and in comparison with the literature data. These compounds proved to be important chemotaxonomic markers in the genus Uncaria. Keywords: Rubiaceae, Uncaria, Oxindole alkaloids, Chemotaxonomy, Uncarine

  1. Analysis of alkaloid phytochemical compounds in the ethanolic ...

    African Journals Online (AJOL)

    The aim of this study was to assess the compounds of alkaloids extracts from the leaves of Datura stramonium, which can be the basis for the synthesis of new antibiotics. ... The chemical compositions of the leaves of ethanolic extract of D.

  2. A novel alkaloid isolated from Crotalaria paulina and identified by NMR and DFT calculations

    Science.gov (United States)

    Oliveira, Ramon Prata; Demuner, Antonio Jacinto; Alvarenga, Elson Santiago; Barbosa, Luiz Claudio Almeida; de Melo Silva, Thiago

    2018-01-01

    Pyrrolizidine alkaloids (PAs) are secondary metabolites found in Crotalaria genus and are known to have several biological activities. A novel macrocycle bislactone alkaloid, coined ethylcrotaline, was isolated and purified from the aerial parts of Crotalaria paulina. The novel macrocycle was identified with the aid of high resolution mass spectrometry and advanced nuclear magnetic resonance techniques. The relative stereochemistry of the alkaloid was defined by comparing the calculated quantum mechanical hydrogen and carbon chemical shifts of eight candidate structures with the experimental NMR data. The best fit between the eight candidate structures and the experimental NMR chemical shifts was defined by the DP4 statistical analyses and the Mean Absolute Error (MAE) calculations.

  3. Skeletal muscle tissue engineering: methods to form skeletal myotubes and their applications.

    Science.gov (United States)

    Ostrovidov, Serge; Hosseini, Vahid; Ahadian, Samad; Fujie, Toshinori; Parthiban, Selvakumar Prakash; Ramalingam, Murugan; Bae, Hojae; Kaji, Hirokazu; Khademhosseini, Ali

    2014-10-01

    Skeletal muscle tissue engineering (SMTE) aims to repair or regenerate defective skeletal muscle tissue lost by traumatic injury, tumor ablation, or muscular disease. However, two decades after the introduction of SMTE, the engineering of functional skeletal muscle in the laboratory still remains a great challenge, and numerous techniques for growing functional muscle tissues are constantly being developed. This article reviews the recent findings regarding the methodology and various technical aspects of SMTE, including cell alignment and differentiation. We describe the structure and organization of muscle and discuss the methods for myoblast alignment cultured in vitro. To better understand muscle formation and to enhance the engineering of skeletal muscle, we also address the molecular basics of myogenesis and discuss different methods to induce myoblast differentiation into myotubes. We then provide an overview of different coculture systems involving skeletal muscle cells, and highlight major applications of engineered skeletal muscle tissues. Finally, potential challenges and future research directions for SMTE are outlined.

  4. A Tony Thomas-Inspired Guide to INSPIRE

    Energy Technology Data Exchange (ETDEWEB)

    O' Connell, Heath B.; /Fermilab

    2010-04-01

    The SPIRES database was created in the late 1960s to catalogue the high energy physics preprints received by the SLAC Library. In the early 1990s it became the first database on the web and the first website outside of Europe. Although indispensible to the HEP community, its aging software infrastructure is becoming a serious liability. In a joint project involving CERN, DESY, Fermilab and SLAC, a new database, INSPIRE, is being created to replace SPIRES using CERN's modern, open-source Invenio database software. INSPIRE will maintain the content and functionality of SPIRES plus many new features. I describe this evolution from the birth of SPIRES to the current day, noting that the career of Tony Thomas spans this timeline.

  5. A Tony Thomas-Inspired Guide to INSPIRE

    International Nuclear Information System (INIS)

    O'Connell, Heath B.

    2010-01-01

    The SPIRES database was created in the late 1960s to catalogue the high energy physics preprints received by the SLAC Library. In the early 1990s it became the first database on the web and the first website outside of Europe. Although indispensible to the HEP community, its aging software infrastructure is becoming a serious liability. In a joint project involving CERN, DESY, Fermilab and SLAC, a new database, INSPIRE, is being created to replace SPIRES using CERN's modern, open-source Invenio database software. INSPIRE will maintain the content and functionality of SPIRES plus many new features. I describe this evolution from the birth of SPIRES to the current day, noting that the career of Tony Thomas spans this timeline.

  6. Risk to human health associated with the environmental occurrence of cyanobacterial neurotoxic alkaloids anatoxins and saxitoxins.

    Science.gov (United States)

    Testai, Emanuela; Scardala, Simona; Vichi, Susanna; Buratti, Franca M; Funari, Enzo

    2016-01-01

    Cyanobacteria are ubiquitous photosynthetic micro-organisms forming blooms and scums in surface water; among them some species can produce cyanotoxins giving rise to some concern for human health and animal life. To date, more than 65 cyanobacterial neurotoxins have been described, of which the most studied are the groups of anatoxins and saxitoxins (STXs), comprising many different variants. In freshwaters, the hepatotoxic microcystins represent the most frequently detected cyanotoxin: on this basis, it could appear that neurotoxins are less relevant, but the low frequency of detection may partially reflect an a priori choice of target analytes, the low method sensitivity and the lack of certified standards. Cyanobacterial neurotoxins target cholinergic synapses or voltage-gated ion channels, blocking skeletal and respiratory muscles, thus leading to death by respiratory failure. This review reports and analyzes the available literature data on environmental occurrence of cyanobacterial neurotoxic alkaloids, namely anatoxins and STXs, their biosynthesis, toxicology and epidemiology, derivation of guidance values and action limits. These data are used as the basis to assess the risk posed to human health, identify critical exposure scenarios and highlight the major data gaps and research needs.

  7. The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom

    Directory of Open Access Journals (Sweden)

    Hannu Hotti

    2017-11-01

    Full Text Available Coniine, a polyketide-derived alkaloid, is poisonous to humans and animals. It is a nicotinic acetylcholine receptor antagonist, which leads to inhibition of the nervous system, eventually causing death by suffocation in mammals. Coniine’s most famous victim is Socrates who was sentenced to death by poison chalice containing poison hemlock in 399 BC. In chemistry, coniine holds two historical records: It is the first alkaloid the chemical structure of which was established (in 1881, and that was chemically synthesized (in 1886. In plants, coniine and twelve closely related alkaloids are known from poison hemlock (Conium maculatum L., and several Sarracenia and Aloe species. Recent work confirmed its biosynthetic polyketide origin. Biosynthesis commences by carbon backbone formation from butyryl-CoA and two malonyl-CoA building blocks catalyzed by polyketide synthase. A transamination reaction incorporates nitrogen from l-alanine and non-enzymatic cyclization leads to γ-coniceine, the first hemlock alkaloid in the pathway. Ultimately, reduction of γ-coniceine to coniine is facilitated by NADPH-dependent γ-coniceine reductase. Although coniine is notorious for its toxicity, there is no consensus on its ecological roles, especially in the carnivorous pitcher plants where it occurs. Lately there has been renewed interest in coniine’s medical uses particularly for pain relief without an addictive side effect.

  8. Investigation of the metabolism of ergot alkaloids in cell culture by fourier transformation mass spectrometry.

    Science.gov (United States)

    Mulac, Dennis; Grote, Anna-Karina; Kleigrewe, Karin; Humpf, Hans-Ulrich

    2011-07-27

    Ergot alkaloids are known toxic secondary metabolites of the fungus Claviceps purpurea occurring in various grains, especially rye products. The liver is responsible for converting the ergot alkaloids into metabolites; however, the toxic impact of these end products of metabolism is still unknown. The aim of this study was to analyze the metabolism of ergot alkaloids in colon and liver cell lines (HT-29, HepG2), as well as in human primary renal cells (RPTEC). It was shown that cells in vitro are able to metabolize ergot alkaloids, forming a variety of metabolic compounds. Significant differences between the used cell types could be identified, and a suitable model system was established using HT-29 cells, performing an intensive metabolism to hydroxylated metabolites. The formed substances were analyzed by coupling of high-performance liquid chromatography with fluorescence detection and Fourier transformation mass spectrometry (HPLC-FLD-FTMS) as a powerful tool to identify known and unknown metabolites.

  9. Prehistoric peyote use: alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas.

    Science.gov (United States)

    El-Seedi, Hesham R; De Smet, Peter A G M; Beck, Olof; Possnert, Göran; Bruhn, Jan G

    2005-10-03

    Two archaeological specimens of peyote buttons, i.e. dried tops of the cactus Lophophora williamsii (Lem.) Coulter, from the collection of the Witte Museum in San Antonio, was subjected to radiocarbon dating and alkaloid analysis. The samples were presumably found in Shumla Cave No. 5 on the Rio Grande, Texas. Radiocarbon dating shows that the calibrated 14C age of the weighted mean of the two individual dated samples corresponds to the calendric time interval 3780-3660 BC (one sigma significance). Alkaloid extraction yielded approximately 2% of alkaloids. Analysis with thin-layer chromatography (TLC) and gas chromatography-mass spectrometry (GC-MS) led to the identification of mescaline in both samples. No other peyote alkaloids could be identified. The two peyote samples appear to be the oldest plant drug ever to yield a major bioactive compound upon chemical analysis. The identification of mescaline strengthens the evidence that native North Americans recognized the psychotropic properties of peyote as long as 5700 years ago.

  10. Plant-derived acetylcholinesterase inhibitory alkaloids for the treatment of Alzheimer's disease

    Directory of Open Access Journals (Sweden)

    Dall'Acqua S

    2013-01-01

    Full Text Available Stefano Dall'AcquaDepartment of Pharmaceutical and Pharmacological Sciences, University of Padova, Padova, ItalyAbstract: The inhibition of acetylcholinesterase (AChE has been one of the most used strategies for the treatment of Alzheimer's disease (AD. The AChE inhibitors (AChE-I produce not only short-term symptomatic effects, but can also play a role in other pathological mechanisms of the disease (eg, formation of amyloid-β plaques, which has renewed interest in the discovery of such inhibitors. Four of the five currently prescribed treatments for AD are AChE-I. Natural alkaloids such as galantamine or alkaloid-related synthetic compounds (such as rivastigmine are considered beneficial for patients with mild-to-moderate AD. However, there is a need for the discovery of more effective compounds and for this reason, plants can still be a potential source of new AChE-I. Findings and advances in knowledge about natural alkaloids as potential new drugs acting as AChE-I will be summarized in this paper.Keywords: quinolizidine, steroidal, indole, isoquinoline

  11. Indole alkaloids from Rauvolfia bahiensis A.DC. (Apocynaceae).

    Science.gov (United States)

    Kato, Lucilia; Marques Braga, Raquel; Koch, Ingrid; Sumiko Kinoshita, Luiza

    2002-06-01

    Four indole alkaloids, 12-methoxy-N(a)-methyl-vellosimine, demethoxypurpeline, 12-methoxyaffinisine, and 12-methoxy-vellosimine, in addition to picrinine, vinorine, raucaffrinoline, normacusine B, norseredamine, seredamine, 10-methoxynormacusine B, norpurpeline and purpeline, were isolated from the bark or leaf extracts of Rauvolfia bahiensis.

  12. Pyrrolizidine alkaloids from Senecio jacobaea affect fungal growth

    NARCIS (Netherlands)

    Hol, W.H.G.; Van Veen, J.A.

    2002-01-01

    We investigated the growth-reducing effects of pyrrolizidine alkaloids (PAs) from Senecio jacobaea on nine plant-associated fungi (five strains of Fusarium oxysporum, two of F. sambucinum, and two of Trichoderma sp). Fungal growth was monitored on water agar media containing different concentrations

  13. Phytotoxicity Assessment of Certain Phytochemical Products Containing Pyrrolizidine Alkaloids

    Directory of Open Access Journals (Sweden)

    Cristina Șeremet Oana

    2013-10-01

    Full Text Available Introduction: Tussilago farfara (coltsfoot, Petasites hybridus (common butterbur, Senecio vernalis (eastern groundsel and Symphytum officinale (comfrey are species traditionally used in phytotherapy that besides the therapeutic compounds contain toxic pyrrolizidine alkaloids (PAs. The aim of the paper is to determine the total PAs content and the phytotoxicity of the above species. Material and methods: The quantitative determination of pyrrolizidine alkaloids is based on the stoichiometric reaction of protonated alkaloids with methyl orange. In acidic conditions the dye is released from the complex and its color is assessed spectrophotometrically using a linear regression curve of senecionine as a standard. The phytotoxicity was assessed by Triticum bioassay that studies the effect of the extracts (0.001-5.00%, w/v upon root elongation (inhibitory concentration - IC50 and on the karyokinetic film. Results: The highest amount of total PAs was found in Senecio vernalis (654.8 ± 35.96 μg/g dry plant and the lowest in Petasites hybridus. The lowest IC50 was found for Tussilago farfara followed by Petasites hybridus, Senecio vernalis, and Symphytum officinale. The results were supported by microscopic examination. Conclusions: The results of the spectrophotometric assay are consistent with the ones found in the literature. All extracts inhibited the elongation of the main root of wheat caryopses, however, no correlation between phytotoxicity and the PAs concentration could be emphasized

  14. Capillary-HPLC with tandem mass spectrometry in analysis of alkaloid dyestuffs - a new approach.

    Science.gov (United States)

    Dąbrowski, Damian; Lech, Katarzyna; Jarosz, Maciej

    2018-05-01

    Development of the identification method of alkaloid compounds in Amur cork tree as well as not examined so far Oregon grape and European Barberry shrubs are presented. The novel approach to separation of alkaloids was applied and the capillary-high-performance liquid chromatography (capillary-HPLC) system was used, which has never previously been reported for alkaloid-based dyestuffs analysis. Its optimization was conducted with three different stationary phases (unmodified octadecylsilane-bonded silica, octadecylsilane modified with polar groups and silica-bonded pentaflourophenyls) as well as with different solvent buffers. Detection of the isolated compounds was carried out using diode-array detector (DAD) and tandem mass spectrometer with electrospray ionization (ESI MS/MS). The working parameters of ESI were optimized, whereas the multiple reactions monitoring (MRM) parameters of MS/MS detection were chosen based on the product ion spectra of the quasi-molecular ions. Calibration curve of berberine has been estimated (y = 1712091x + 4785.03 with the correlation coefficient 0.9999). Limit of detection and limit of quantification were calculated to be 3.2 and 9.7 ng/mL, respectively. Numerous alkaloids (i.e., berberine, jatrorrhizine and magnoflorine, as well as phellodendrine, menisperine and berbamine) were identified in the extracts from alkaloid plants and silk and wool fibers dyed with these dyestuffs, among them their markers. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  15. Employing Two-stage Derivatisation and GC-MS to Assay for Cathine and Related Stimulant Alkaloids across the Celastraceae.

    Science.gov (United States)

    Tembrock, Luke R; Broeckling, Corey D; Heuberger, Adam L; Simmons, Mark P; Stermitz, Frank R; Uvarov, Jessica M

    2017-07-01

    Catha edulis (qat, khat, mirra) is a woody plant species that is grown and consumed in East Africa and Yemen for its stimulant alkaloids cathinone, cathine and norephedrine. Two Celastraceae species, in addition to qat, have been noted for their stimulant properties in ethnobotanical literature. Recent phylogenetic reconstructions place four genera in a clade sister to Catha edulis, and these genera are primary candidates to search for cathine and related alkaloids. Determine if cathine or related alkaloids are present in species of Celastraceae other than Catha edulis. Leaf samples from 43 Celastraceae species were extracted in water followed by basification of the aqueous extract and partitioning with methyl-t-butyl ether to provide an alkaloid-enriched fraction. The extract was derivatised in a two-stage process and analysed using GC-MS for the presence of cathine. Related alkaloids and other metabolites in this alkaloid-enriched fraction were tentatively identified. Cathinone, cathine and norephedrine were not detected in any of the 43 Celastraceae species assayed other than Catha edulis. However, the phenylalanine- or tyrosine-derived alkaloid phenylethylamine was identified in five species. Nine species were found to be enriched for numerous sterol- and terpene-like compounds. These results indicate that cathine is unique to Catha edulis, and not the compound responsible for the stimulant properties reported in related Celastraceae species. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  16. Amides and an alkaloid from Portulaca oleracea.

    Science.gov (United States)

    Kokubun, Tetsuo; Kite, Geoffrey C; Veitch, Nigel C; Simmonds, Monique S J

    2012-08-01

    A total of 16 phenolic compounds, including one new and five known N-cinnamoyl phenylethylamides, one new pyrrole alkaloid named portulacaldehyde, five phenylpropanoid acids and amides, and derivatives of benzaldehyde and benzoic acid, were isolated and identified from a polar fraction of an extract of Portulaca oleracea. Their structures were determined through spectroscopic analyses.

  17. Blood pyrrole-protein adducts as a diagnostic and prognostic index in pyrrolizidine alkaloid-hepatic sinusoidal obstruction syndrome

    Directory of Open Access Journals (Sweden)

    Gao H

    2015-08-01

    Full Text Available Hong Gao,1,* Jianqing Q Ruan,2,* Jie Chen,1 Na Li,2 Changqiang Q Ke,3 Yang Ye,3–5 Ge Lin,2,4,5 Jiyao Y Wang1,61Department of Gastroenterology, Zhongshan Hospital, Fudan University, Shanghai, People’s Republic of China; 2School of Biomedical Sciences, Chinese University of Hong Kong, Hong Kong; 3Shanghai Institute of Materia Medica, Shanghai, People’s Republic of China; 4Joint Research Laboratory for Promoting Globalization of Traditional Chinese Medicines, Shanghai Institute of Materia Medica, 5Chinese University of Hong Kong, Hong Kong; 6Center of Evidence-Based Medicine Fudan University, Shanghai, People’s Republic of China*These authors contributed equally to this work and share first authorship Background: The diagnosis of hepatic sinusoidal obstruction syndrome (HSOS induced by pyrrolizidine alkaloids is mainly based on clinical investigation. There is currently no prognostic index. This study evaluated the quantitative measurement of blood pyrrole-protein adducts (PPAs as a diagnostic and prognostic index for pyrrolizidine alkaloid-induced HSOS.Methods: Suspected drug-induced liver injury patients were prospectively recruited. Blood PPAs were quantitatively measured using ultra-performance liquid chromatography-tandem mass spectrometry. Patients’ age, sex, biochemistry test results, and a detailed drug history were recorded. The patients were divided into two groups, ie, those with HSOS induced by pyrrolizidine alkaloid-containing drugs and those with liver injury induced by drugs without pyrrolizidine alkaloids. The relationship between herb administration, clinical outcomes, blood sampling time, and blood PPA concentration in pyrrolizidine alkaloid-associated HSOS patients was analyzed using multiple linear regression analysis.Results: Forty patients met the entry criteria, among whom 23 had pyrrolizidine alkaloid-associated HSOS and 17 had liver injury caused by drugs without pyrrolizidine alkaloids. Among the 23

  18. Correlations between Antioxidant Activity and Alkaloids and Phenols of Maca (Lepidium meyenii

    Directory of Open Access Journals (Sweden)

    Jin Gan

    2017-01-01

    Full Text Available The antioxidant capacity of maca has been considered to be the basis for other bioactivities, and revealing the active antioxidant compounds would help to elucidate a variety of bioactive compounds. In this study, the correlation between the antioxidant activity of maca and secondary metabolites, including ferric reducing antioxidant potential (FRAP, hydroxyl radical scavenging ability (HRSA, lipid peroxidation inhibition ability (LPIA, total phenolic contents (TPCs, total alkaloid contents (TACs, and total sterol contents (TSCs, was investigated by measuring. Chloroform was selected to be an efficient extraction solvent for antioxidant compounds in maca by polarity fractions test. The results showed that TPC exhibited significant linear correlations (P<0.05 to FRAP and LPIA, while TAC had significant linear correlations (P<0.05 to FRAP, HRSA, and LPIA. These results suggested that alkaloids and phenols were the most important substances for the antioxidation of maca, of which the antioxidant effect of alkaloids seemed to be higher than that of phenols.

  19. Process optimization and insecticidal activity of alkaloids from the ...

    African Journals Online (AJOL)

    Process optimization and insecticidal activity of alkaloids from the root bark of Catalpa ovata G. Don by response surface methodology. ... Tropical Journal of Pharmaceutical Research. Journal Home · ABOUT THIS JOURNAL · Advanced ...

  20. [Pharmacokinetic of four alkaloids of Yanshu injection in Beagel dogs].

    Science.gov (United States)

    Liu, Jiping; Xue, Mei; Huang, Xin; Wang, Shu; Jiang, Zhenzhou; Zhang, Luyong

    2012-06-01

    For studying the pharmacokinetic of Yanshu injections in Beagel dogs, a sensitive and reproducible LC-MS method for quantitative determination of matrine, oxymatrine, sophocarpine and oxysophocarpine in dog's plasma were developed and validated using monocrotaline as an internal standard after iv of Yanshu injections (Sophorae Flavescentis Radix and Heterosmilacis Japonicae Rhizoma). The separation of plasma samples was performed on a CN column by isocratic elution with methanol-10 mmol x L(-1) NH4Ac-0.02% HCOOH-H2O 90:10 as the mobile phase. The plasma concentration of four kinds of alkaloids were calculated in dog plasta by detection of healthy dogs given Yanshu injection fluid after in twelve hours of plasma samples, All data of concentration-time of four kinds of alkaloids were treated with pharmacokinetics program DAS 2. 0. MT, OMT, SP and OSP have a good linear relationship in 0.01-16.0, 0.02-60.0, 0.01-4.0, 0.02-16.0 mg x L(-1), respectively. The average recoveries were more than 90% and the RSD of precision and stability of the test were less than 6.4% iv 1.2 g x kg(-1) Yanshu injection, four kinds of alkaloids in rats meet the two-compartment open pharmacokinetic model, Cmax and the concentration of the original liquid in the proportion of the basic line, the AUC(0-infinity) of matrine and oxymatrine, sophocarpine and oxysophocarpine compared to the original both in the proportion of liquid increases, the MRT(0-infinity) and t(1/2z) of matrine and sophocarpine were less than oxymatrine and oxysophocarpine; four kinds of alkaloids apparent volume of distribution matrine > oxymatrine, sophocarpine > oxysophocarpine. A method with high recovery rate and good stabilitywas established to determine the blood concentration of MT, OMT, SP, OSP in Yanshu injection and applied in its pharmacokinetics successfully.

  1. Spatiotemporal oscillations of morphinan alkaloids in opium poppy

    Indian Academy of Sciences (India)

    Mahdi Rezaei

    2018-04-30

    Apr 30, 2018 ... biosynthesis is coordinated tightly by the enzymatic function of SalAT enzyme. Meanwhile, despite ... Therefore, determination of the alkaloid profile of each individual plant .... well-known technique, IMS offers low detection limit, fast response ...... ion mobility spectrometry with ammonia reagent gas. Talanta.

  2. Rauvomines A and B, Two Monoterpenoid Indole Alkaloids from Rauvolfia vomitoria.

    Science.gov (United States)

    Zeng, Jun; Zhang, Dong-Bo; Zhou, Pan-Pan; Zhang, Qi-Li; Zhao, Lei; Chen, Jian-Jun; Gao, Kun

    2017-08-04

    Two unusual normonoterpenoid indole alkaloids rauvomine A (1) and rauvomine B (2), together with two known compounds peraksine (3) and alstoyunine A (4), were isolated from the aerial parts of Rauvolfia vomitoria. The structures with absolute configurations of 1 and 2 were elucidated by spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compound 2 is a novel C 18 normonoterpenoid indole alkaloid with a substituted cyclopropane ring that forms an unusual 6/5/6/6/3/5 hexcyclic rearranged ring system. The plausible biogenetic pathways of 1 and 2 were proposed. Compound 2 exhibited significant anti-inflammatory activity.

  3. Fire ant venom alkaloids act as key attractants for the parasitic phorid fly, Pseudacteon tricuspis (Diptera: Phoridae)

    Science.gov (United States)

    Chen, Li; Sharma, Kavita R.; Fadamiro, Henry Y.

    2009-12-01

    The phorid fly, Pseudacteon tricuspis Borgmeier, is an introduced parasitoid of imported fire ants, Solenopsis spp., in the USA. Although the assumption that phorid flies use fire ant alarm pheromones for host location is probably true, we demonstrated in a previous study the possible involvement of other ant semiochemicals in the response of P. tricuspis to fire ants. This study was conducted to determine the glandular sources and identity of the semiochemicals mediating this interaction. First, we tested the electroantennogram response of P. tricuspis to extracts of key body parts and glands of workers of the red imported fire ant, S. invicta Buren. The results confirm that the poison (venom) gland/sac is the key source of compounds which elicited strong antennal activity in P. tricuspis. Follow-up studies were conducted by using a combination of bioassay-guided fractionation and behavioral bioassays to test the hypothesis that attraction of this parasitoid to fire ants is mediated by venom alkaloids. The results confirm the response of P. tricuspis to physiologically relevant amounts of the two venom alkaloid fractions ( cis and trans alkaloid fractions) of S. invicta. Further analysis by coupled gas chromatography-electroantennogram detection revealed nine venom alkaloid components including two novel 2,6-dialkylpiperideines that elicited significant antennal activity in P. tricuspis. This is the first demonstration of the role of venom alkaloids of ants as attractants for their natural enemies. We propose a semiochemical-mediated host location mechanism for P. tricuspis involving both alarm pheromones and venom alkaloids. The ecological significance of these findings, including the attraction of male P. tricuspis to fire ant venom alkaloids, possibly for mate location, is discussed.

  4. Alkaloids as taxonomic markers in some species of Magnolia L. and Liriodendron L.

    Directory of Open Access Journals (Sweden)

    Mirosław Furmanowa

    2014-01-01

    Full Text Available Some Magnoliaceae cultivated in Poland were investigated: Liriodendron tulipifera L. and 6 species of magnolia: Magnolia acuminata L., M. denudata Desr., M. kobus DC., M. obovata Thunb., M. salicifolia Maxim. and M. tripetala L. For alkaloid detection in the leaves thin-,layer chromatography was used. In Liriodendron tulipifera L. and in all the Magnolia species liriodenine which exhibits cytostatic activity was detected. The extract of Liriodendron tulipifera L. leaves showed, beside liriodenine other spots on the chromatogram than did the magnolias. Alkaloids can be utilized in the chemotaxonomy of Magnoliaceae as a diagnostic trait. The results of the investigations indicate a certain distinctiveness of M. acuminata L., in agreement with those obtained by way of numerical taxonomy. Most similar as regards alkaloid content in leaves are M. obovata Thunb. and M. tripetala L.

  5. Safety assessment of food and herbal products containing hepatotoxic pyrrolizidine alkaloids: interlaboratory consistency and the importance of N-oxide determination.

    Science.gov (United States)

    Cao, Yu; Colegate, Steven M; Edgar, John A

    2008-01-01

    Two recent mass spectrometry-based reports concerning Senecio scandens yielded remarkably dissimilar pyrrolizidine alkaloid constituents. In both studies, and in a related analysis of Senecio scandens and Tussilago farfara using micellar electrokinetic chromatography, the presence of hazardous N-oxides of the alkaloids was either not considered or was inadequately considered. This raises concerns about the effectiveness of the methodologies used in these, and similar, studies in assessing the pyrrolizidine alkaloid content and the safety of food, food supplements and medicines for human use. To highlight essential analytical requirements for confident assessment of pyrrolizidine alkaloid-related safety of food and herbal products for human use. Direct infusion-ESI MS and HPLC-ESI MS were used to analyse samples derived from liquid-liquid partitioning experiments and from strong cation exchange, solid-phase extraction of pyrrolizidine alkaloids and their N-oxides. A simple solvent partitioning experiment using pure senecionine and senecionine-N-oxide, two constituents reported in one of the mass spectrometry-based studies of S. scandens, clearly demonstrated the inadequacy of the reported method to detect and quantitate hazardous pyrrolizidine alkaloid N-oxide components. A preliminary LCMS analysis of commercially-prepared extracts of comfrey roots (Symphytum officinale and S. uplandicum s. l.) was used as a model to highlight the analytical importance of N-oxides in the safety assessment of pyrrolizidine alkaloid-containing medicinal herbs. This study highlighted significant differences in the reported identification of pyrrolizidine alkaloids from the same plant species, and clearly demonstrated the inadequacy of some procedures to include N-oxides in the assessment of pyrrolizidine alkaloid-related safety of food and herbal products.

  6. Chemotaxonomic studies of mesembrine-type alkaloids in Sceletium plant species

    Directory of Open Access Journals (Sweden)

    Srinivas Patnala

    2013-03-01

    Full Text Available Complementary medicines containing the succulent herb Sceletium are being sold without information regarding their phytochemical contents, which is essential for the quality control of medicines. Furthermore, several different Sceletium species exist and little has been reported on the alkaloidal identities and contents of the various species. We therefore conducted phytochemical investigations on six selected Sceletium specimens, identified on the basis of their venation pattern as either ‘emarcidum’ or ‘tortuosum’ type. The tortuosum type consisted of S. tortuosum, S. expansum and S. strictum, whereas the emarcidum type consisted of S. emarcidum, S. exalatum and S. rigidum. Analysis was conducted by high-performance liquid chromatography with UV and alkaloids were identified by online mass spectroscopy.

  7. Flavonols, leuco-anthocyanins, cinnamic acids, and alkaloids in dried leaves of some Asiatic and Malesian Simaroubaceae

    NARCIS (Netherlands)

    Nooteboom, H.P.

    1966-01-01

    Herbarium specimens of 13 species of the Simaroubaceae were investigated on phenolic compounds present in their hydrolised leaf extracts and on the presence of alkaloids (table 2). Leucoanthocyanins, myricetin, gallic acid, ellagic acid, as well as alkaloids were demonstrated to occur rather

  8. Identifying the related compounds using electrospray ionization tandem mass spectrometry: bromotyrosine alkaloids from marine sponge Psammaplysilla purpurea

    Digital Repository Service at National Institute of Oceanography (India)

    Tilvi, S.; DeSouza, L.

    electrospray ionization tandem mass spectrometry (ESI-MS/MS). This sponge has tremendous chemical diversity of bromotyrosine alkaloids. Here we have used the proteomics approach in identifying related bromotyrosine alkaloids based on the predicated mass...

  9. An NPF transporter exports a central monoterpene indole alkaloid intermediate from the vacuole

    DEFF Research Database (Denmark)

    Payne, Richard; Xu, Deyang; Foureau, Emilien

    2017-01-01

    Plants sequester intermediates of metabolic pathways into different cellular compartments, but the mechanisms by which these molecules are transported remain poorly understood. Monoterpene indole alkaloids, a class of specialized metabolites that includes the anticancer agent vincristine, antimal......Plants sequester intermediates of metabolic pathways into different cellular compartments, but the mechanisms by which these molecules are transported remain poorly understood. Monoterpene indole alkaloids, a class of specialized metabolites that includes the anticancer agent vincristine...

  10. Synthesis of the new derivatives of alkaloid glaucine

    International Nuclear Information System (INIS)

    Mukusheva, G.K.; Zhumagalieva, Zh.Zh.; Turmukhambetov, A.Zh.; Kazantsev, A.V.

    2005-01-01

    On the basis of aporphine alkaloid glaucine by reactions of halogenation, amino-methylation, acetylation and with esters of boronic acid new derivatives of glaucine were synthesized. The structures of obtained compounds were determined on basis of IR, 13 C, 1 H, 11 B NMR spectral data

  11. Tall Fescue Alkaloids Bind Serotonin Receptors in Cattle

    Science.gov (United States)

    The serotonin (5HT) receptor 5HT2A is involved in the tall fescue alkaloid-induced vascular contraction in the bovine periphery. This was determined by evaluating the contractile responses of lateral saphenous veins biopsied from cattle grazing different tall fescue/endophyte combinations. The contr...

  12. Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle.

    Science.gov (United States)

    Anagyrine, a teratogenic quinolizidine alkaloid found in certain Lupinus spp., has been proposed to undergo metabolism by pregnant cattle to a piperidine alkaloid which acts inhibit fetal movement, the putative mechanism behind crooked calf syndrome. The objective of this study was to test the hypot...

  13. Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activities of β-Carboline and Quinoline Alkaloids Derivatives from the Plants of Genus Peganum

    Directory of Open Access Journals (Sweden)

    Ting Zhao

    2013-01-01

    Full Text Available It was reported that the main chemical constituents in plants of genus Peganum were a serial of β-carboline and quinoline alkaloids. These alkaloids were quantitatively assessed for selective inhibitory activities on acetylcholinesterase (AChE and butyrylcholinesterase (BChE by in vitro Ellman method. The results indicated that harmane was the most potent selective AChE inhibitor with an IC50 of 7.11 ± 2.00 μM and AChE selectivity index (SI, IC50 of BChE/IC50 of AChE of 10.82. Vasicine was the most potent BChE inhibitor with feature of dual AChE/BChE inhibitory activity, with an IC50 versus AChE/BChE of 13.68 ± 1.25/2.60 ± 1.47 μM and AChE SI of 0.19. By analyzing and comparing the IC50 and SI of those chemicals, it was indicated that the β-carboline alkaloids displayed more potent AChE inhibition but less BChE inhibition than quinoline alkaloids. The substituent at the C7 position of the β-carboline alkaloids and C3 and C9 positions of quinoline alkaloids played a critical role in AChE or BChE inhibition. The potent inhibition suggested that those alkaloids may be used as candidates for treatment of Alzheimer’s disease. The analysis of the quantitative structure-activity relationship of those compounds investigated might provide guidance for the design and synthesis of AChE and BChE inhibitors.

  14. Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids.

    Directory of Open Access Journals (Sweden)

    Michal Rájecký

    Full Text Available Quaternary benzo[c]phenanthridine alkaloids are secondary metabolites of the plant families Papaveraceae, Rutaceae, and Ranunculaceae with anti-inflammatory, antifungal, antimicrobial and anticancer activities. Their spectral changes induced by the environment could be used to understand their interaction with biomolecules as well as for analytical purposes. Spectral shifts, quantum yield and changes in lifetime are presented for the free form of alkaloids in solvents of different polarity and for alkaloids bound to DNA. Quantum yields range from 0.098 to 0.345 for the alkanolamine form and are below 0.033 for the iminium form. Rise of fluorescence lifetimes (from 2-5 ns to 3-10 ns and fluorescence intensity are observed after binding of the iminium form to the DNA for most studied alkaloids. The alkanolamine form does not bind to DNA. Acid-base equilibrium constant of macarpine is determined to be 8.2-8.3. Macarpine is found to have the highest increase of fluorescence upon DNA binding, even under unfavourable pH conditions. This is probably a result of its unique methoxy substitution at C12 a characteristic not shared with other studied alkaloids. Association constant for macarpine-DNA interaction is 700000 M(-1.

  15. Effects of alkaloid extracts of mesquite pod on the products of in vitro rumen fermentation.

    Science.gov (United States)

    de Jesus Pereira, Taiala Cristina; Pereira, Mara Lúcia Albuquerque; Moreira, Jeruzia Vitória; Azevêdo, José Augusto Gomes; Batista, Ronan; de Paula, Vanderlúcia Fonseca; Oliveira, Brena Santos; de Jesus Dos Santos, Edileusa

    2017-02-01

    The objective of this study was to evaluate the effects of alkaloid extracts of Prosopis juliflora (Sw.) D.C. pods obtained by two extraction methods as compared with sodium monensin on the gas production kinetic, mitigation of methane, and rumen fermentation products using wheat bran or Tifton 85 hay as substrates, by the semi-automatic in vitro gas production technique. A completely randomized design was adopted, and two natural additives were tested made from mesquite pod (alkaloid extract I and alkaloid extract II) at three levels (3.9, 7.9, and 12 μg), sodium monensin 5 μM (positive control), and no inclusion of additives (negative control). The volume of gases produced by the degradation of the fibrous fraction of wheat bran was influenced by the concentration of the extract I added to the medium, and the amounts of 7.9 and 12 μg were equal to monensin at the lowest value. The degradation rate of the fibrous carbohydrates with additive extract I at 12 μg was lower in relation to monensin. When Tifton 85 hay was utilized, alkaloid extract I provided a shorter colonization time as compared with monensin at the added amounts of 7.9 and 12 μg and higher production of gases from the fibrous fraction but without interfering with the total volume of gases produced during 96 h of fermentation of carbohydrates. In the periods of 12 and 24 h of incubation, utilizing alkaloid extract I, the mean values of methane production with wheat bran and Tifton 85 hay were lower than monensin (p < 0.05) when the respective amounts of 7.9 and 12 μg were added. Alkaloid extract I has similar potential to sodium in reducing production of total gases, methane, and the acetate/propionate ratio.

  16. New bromotyrosine alkaloids from the marine sponge Psammaplysilla purpurea

    Digital Repository Service at National Institute of Oceanography (India)

    Tilvi, S.; Rodrigues, C; Naik, C; Parameswaran, P.S.; Wahidullah, S.

    Seven new bromotyrosine alkaloids Purpurealidin A, B, C, D, F, G, H and the known compounds Purealidin Q, Purpurealidin E, 16-Debromoaplysamine-4 and Purpuramine I have been isolated from the marine sponge Psammaplysilla purpurea. Their structure...

  17. Simultaneous determination of aconitum alkaloids in rat body fluids ...

    African Journals Online (AJOL)

    performance liquid chromatography. ... were in the range of 85.63 - 90.94% for all analysis of the three aconitum alkaloids with relative standard deviations (RSD) below 14%. Positive linear relationships were observed in correlation coefficients that ...

  18. Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay.

    Science.gov (United States)

    Schnitzius, J M; Hill, N S; Thompson, C S; Craig, A M

    2001-05-01

    Ergot alkaloids present in endophyte-infected (E+) tall fescue cause fescue toxicosis and other toxic effects in livestock that consume infected plant tissue, leading to significant financial losses in livestock production each year. The predominant method currently in use for quantifying ergot alkaloid content in plant tissue is through high-performance liquid chromatography (HPLC), which quantifies the amount of ergovaline, one of many ergot alkaloids in E+ plant tissue. The enzyme-linked immunosorbent assay (ELISA) method used in this study detects quantities of nonspecific ergot alkaloids and therefore accounts for greater amounts of the total ergot alkaloid content in E+ tissue than does HPLC. The ELISA can also be used to more expediently analyze a larger number of forage samples without sophisticated and costly analytical equipment and therefore could be more desirable in a diagnostic setting. The purpose of this study was to evaluate the between-day and within-run variability of the ELISA and to determine the binding efficiency of 6 ergot alkaloids to the 15F3.E5 antibody used in the competitive ELISA to ascertain its feasibility as a quick analysis tool for ergot alkaloids. Straw samples had an average coefficient of variation (CV) for concentration of 10.2% within runs and 18.4% between runs, and the seed samples had an average CV for concentration of 13.3% within runs and 24.5% between runs. The grass tissue-based lysergic acid standard curve calculated from the ELISA had an average r2 of 0.99, with a CV of 2.1%. Ergocryptine, ergocristine, ergocornine, and ergotamine tartrate did not bind strongly to the 15F3.E5 antibody because of the presence of large side groups on these molecules, which block their binding to the antibody, whereas ergonovine and ergonovine maleate were bound much more efficiently because of their structural similarity to lysergic acid. Clarified rumen fluid was tested as an additional matrix for use in the ergot alkaloid competitive

  19. Kinds of inspiration in interaction design

    DEFF Research Database (Denmark)

    Halskov, Kim

    2010-01-01

    In this paper, we explore the role of sources of inspiration in interaction design. We identify four strategies for relating sources of inspiration to emerging ideas: selection; adaptation; translation; and combination. As our starting point, we argue that sources of inspiration are a form...... of knowledge crucial to creativity. Our research is based on empirical findings arising from the use of Inspiration Card Workshops, which are collaborative design events in which domain and technology insight are combined to create design concepts. In addition to the systematically introduced sources...... of inspiration that form part of the workshop format, a number of spontaneous sources of inspiration emerged during these workshops....

  20. Effects of combination treatment of 60Co γ-rays irradiation and no on alkaloid production and plbs growth of hybrid dendrobium

    International Nuclear Information System (INIS)

    Jin Qing; Cai Yongping; Lin Yi; Lu Ruihong

    2010-01-01

    The effects of 60 Co γ-rays irradiation, SNP (sodium nitroprusside, used as the donor) alone and their combination treatments on the alkaloids production and protocorm-like bodies (PLBs) growth were investigated in suspension cultures of Hybrid dendrobium. The results showed that either 60 Co γ-rays or SNP, and their combined treatments could enhance the accumulation of alkaloids, but restricted the PLBs growth, especially the combined treatments had the accumulative effect on the alkaloids production. The alkaloids content achieved 0.0676% with the optimum combined treatment of 0.1 mmol/L sodium nitroprusside and 10 Gy 60 Co γ-rays irradiation. The alkaloids production of unit medium was 6.35-fold higher than that in untreated PLBs cultures and was significantly different from the treatment of 60 Co γ-rays or SNP at P < 0.01 level. Both Nw-Nitro-L-arginine methl ester hydrochloride and carboxy 2-phenyl-4, 4, 5, 5-tetramethylimidazoline-1-oxyl 3-oxide inhibitors could inhibit the accumulation of alkaloids. With the combined treatment, the activities of POD, SOD and CAT were changed, which perhaps mediated the alkaloids production and PLBs growth. (authors)

  1. Supercritical fluid extraction and chromatographic analysis (HRGC-FID and HRGC-MS of Lupinus spp. alkaloids

    Directory of Open Access Journals (Sweden)

    Nossack Ana C.

    2000-01-01

    Full Text Available The alkaloid extracts from Lupinus spp., obtained by conventional methods (maceration/sonication - solid phase extraction; maceration/sonication - liquid-liquid extraction and SFE (supercritical fluid extraction using CO2 and modified CO2 (CO2/MeOH, CO2/EtOH, CO2/iPrOH and CO2/H2O were analysed by HRGC-FID (high resolution gas chromatography - flame ionization detector and HRGC-MS (high resolution gas chromatography - mass spectrometry. The HRGC-FID quantitative analyses were performed with an internal standard method for quantification of lupanine, multiflorine and a spartein-like alkaloid. HRGC-MS allowed identification of the chemical constituents (alkaloids and other compounds from these extracts.

  2. Use of analogues to build technologists' confidence: NAnet

    International Nuclear Information System (INIS)

    Noseck, Ulrich

    2008-01-01

    The relevance of analogues to radioactive waste management stems from the long timescales that have to be considered. Periods up to a million or more years into the future need to be considered and these are beyond experimental investigation and human experience. Within the last years the term 'Natural Analogue' has got a much wider meaning and includes man-made analogues as well. The role of natural analogues in the safety case depends amongst others on the time scale to be covered. Therefore, it is useful to classify them by the time period addressed in the study. Here it is referred to: industrial analogues which started earliest 150 years ago, archaeological analogues, which cover time frames between the past 10 000 and 150 years, and geological analogues, which usually cover time frames of more than 10 000 years and in most cases more than million years. The current interest in analogues in different countries is reflected by several recent review projects with emphasis on the application of natural analogue study results in performance assessment. The most recent international review was performed within the 5. EURATOM Framework of the EC by the NAnet project, a network on the review of natural analogue studies with emphasis on the application of analogues in long-term safety assessment and communication. The overall aim of the NAnet project was to review the past and present use and understanding of natural analogues, and to make recommendations for their future use. The project covered 'traditional' natural analogue studies, such as large-scale investigations of radionuclide transport around uranium ore bodies, and process or mechanistic analogue studies such as those examining natural glass and bentonite clay stability. To complete the picture, a restricted range of other studies of natural systems which employ a similar philosophy to analogues was also included in the scope. These included studies which have examined radionuclide transport and retardation

  3. Alkaloids from Juglans Mandshurica maxim induce distinctive cell death in hepatocellular carcinoma cells.

    Science.gov (United States)

    Lou, Li-Li; Cheng, Zhuo-Yang; Guo, Rui; Yao, Guo-Dong; Song, Shao-Jiang

    2017-12-15

    The aim of this work was to further investigate the anticancer potential of Juglans mandshurica Maxim, including the separation of active constituents and their anti-proliferative effects with underlying mechanism of action. Five alkaloids (1-5) were isolated from the bark of J. mandshurica. Among them, 1 showed the highest cytotoxic activities against Hep3B and HepG2 cells with an IC50 values of 61.80 and 56.24 μM, respectively. Therefore, the cellular mechanism involved 1 was subsequently studied. Our results showed that 1 markedly caused apoptosis and autophagy, but without cell cycle arrest in HepG2 cells. Interestingly, only autophagic cell death was induced in 1-treated Hep3B cells. It is concluded that the isolated alkaloids exerted a certain anti-hepatoma potential, and our results may provide a basis for the further investigation of the alkaloids extracted from J. mandshurica.

  4. Polyhydroxylated alkaloids isolated from mulberry trees (Morusalba L.) and silkworms (Bombyx mori L.).

    Science.gov (United States)

    Asano, N; Yamashita, T; Yasuda, K; Ikeda, K; Kizu, H; Kameda, Y; Kato, A; Nash, R J; Lee, H S; Ryu, K S

    2001-09-01

    New polyhydroxylated alkaloids, (2R,3R,4R)-2-hydroxymethyl-3,4-dihydroxypyrrolidine-N-propionamide from the root bark of Morus alba L., and 4-O-alpha-D-galactopyranosyl-calystegine B(2) and 3 beta,6 beta-dihydroxynortropane from the fruits, were isolated by column chromatography using a variety of ion-exchange resins. Fifteen other polyhydroxylated alkaloids were also isolated. 1-Deoxynojirimycin, a potent alpha-glucosidase inhibitor, was concentrated 2.7-fold by silkworms feeding on mulberry leaves. Some alkaloids contained in mulberry leaves were potent inhibitors of mammalian digestive glycosidases but not inhibitors of silkworm midgut glycosidases, suggesting that the silkworm has enzymes specially adapted to enable it to feed on mulberry leaves. The possibility of preventing the onset of diabetes and obesity using natural dietary supplements containing 1-deoxynojirimycin and other alpha-glucosidase inhibitors in high concentration is of great potential interest.

  5. Molecular weight determination of bisbenzyl-isoquinoline alkaloids by 252Cf-plasma desorption mass spectrometer

    International Nuclear Information System (INIS)

    Kohno, Hiroyuki; Tatsunami, Shinobu; Hiroi, Tomoko; Kouyama, Hiroshi; Taniguchi, Masashi; Yago, Nagasumi; Nakamura, Iwao

    1995-01-01

    Bisbenzylisoquinoline alkaloids of Stephania cepharantha have been used for various clinical purposes and recently reevaluated as stimulators of interleukin secretion in tissues. We analyzed molecular stuctures of bisbenzylisoquinoline alkaloids by determining their molecular weights using the 252 Cf-plasma desorption mass spectrometry (PDMS). The spectra were accumulated for 500 000 fission events. The acceleration voltage used here was 15 kV. Samples were analyzed using nitrocellulose-coated sample targets. Of the 5 alkaloids studied here, cepharanthine gave a main peak of molecular weight of 606.1 for the theoretical molecular weight of 606.7. The other minor peaks were considered to be demethylated fragment ions. 252 Cf-PDMS should be quite useful in studying structure, metabolism and pharmacokinetics of various drugs with extremely low coefficients of variation. (author)

  6. An OMIC approach to elaborate the antibacterial mechanisms of different alkaloids.

    Science.gov (United States)

    Avci, Fatma Gizem; Sayar, Nihat Alpagu; Sariyar Akbulut, Berna

    2018-05-01

    Plant-derived substances have regained interest in the fight against antibiotic resistance owing to their distinct antimicrobial mechanisms and multi-target properties. With the recent advances in instrumentation and analysis techniques, OMIC approaches are extensively used for target identification and elucidation of the mechanism of phytochemicals in drug discovery. In the current study, RNA sequencing based transcriptional profiling together with global differential protein expression analysis was used to comparatively elaborate the activities and the effects of the plant alkaloids boldine, bulbocapnine, and roemerine along with the well-known antimicrobial alkaloid berberine in Bacillus subtilis cells. The transcriptomic findings were validated by qPCR. Images from scanning electron microscope were obtained to visualize the effects on the whole-cells. The results showed that among the three selected alkaloids, only roemerine possessed antibacterial activity. Unlike berberine, which is susceptible to efflux through multidrug resistance pumps, roemerine accumulated in the cells. This in turn resulted in oxidative stress and building up of reactive oxygen species, which eventually deregulated various pathways such as iron uptake. Treatment with boldine or bulbocapnine slightly affected various metabolic pathways but has not changed the growth patterns at all. Copyright © 2018 Elsevier Ltd. All rights reserved.

  7. Effect of Iboga alkaloids on µ-opioid receptor-coupled G protein activation.

    Directory of Open Access Journals (Sweden)

    Tamara Antonio

    Full Text Available The iboga alkaloids are a class of small molecules defined structurally on the basis of a common ibogamine skeleton, some of which modify opioid withdrawal and drug self-administration in humans and preclinical models. These compounds may represent an innovative approach to neurobiological investigation and development of addiction pharmacotherapy. In particular, the use of the prototypic iboga alkaloid ibogaine for opioid detoxification in humans raises the question of whether its effect is mediated by an opioid agonist action, or if it represents alternative and possibly novel mechanism of action. The aim of this study was to independently replicate and extend evidence regarding the activation of μ-opioid receptor (MOR-related G proteins by iboga alkaloids.Ibogaine, its major metabolite noribogaine, and 18-methoxycoronaridine (18-MC, a synthetic congener, were evaluated by agonist-stimulated guanosine-5´-O-(γ-thio-triphosphate ([(35S]GTPγS binding in cells overexpressing the recombinant MOR, in rat thalamic membranes, and autoradiography in rat brain slices.In rat thalamic membranes ibogaine, noribogaine and 18-MC were MOR antagonists with functional Ke values ranging from 3 uM (ibogaine to 13 uM (noribogaine and 18MC. Noribogaine and 18-MC did not stimulate [(35S]GTPγS binding in Chinese hamster ovary cells expressing human or rat MORs, and had only limited partial agonist effects in human embryonic kidney cells expressing mouse MORs. Ibogaine did not did not stimulate [(35S]GTPγS binding in any MOR expressing cells. Noribogaine did not stimulate [(35S]GTPγS binding in brain slices using autoradiography. An MOR agonist action does not appear to account for the effect of these iboga alkaloids on opioid withdrawal. Taken together with existing evidence that their mechanism of action also differs from that of other non-opioids with clinical effects on opioid tolerance and withdrawal, these findings suggest a novel mechanism of action, and

  8. Proteomics of Skeletal Muscle

    DEFF Research Database (Denmark)

    Deshmukh, Atul

    2016-01-01

    , of altered protein expressions profiles and/or their posttranslational modifications (PTMs). Mass spectrometry (MS)-based proteomics offer enormous promise for investigating the molecular mechanisms underlying skeletal muscle insulin resistance and exercise-induced adaptation; however, skeletal muscle......Skeletal muscle is the largest tissue in the human body and plays an important role in locomotion and whole body metabolism. It accounts for ~80% of insulin stimulated glucose disposal. Skeletal muscle insulin resistance, a primary feature of Type 2 diabetes, is caused by a decreased ability...... of muscle to respond to circulating insulin. Physical exercise improves insulin sensitivity and whole body metabolism and remains one of the most promising interventions for the prevention of Type 2 diabetes. Insulin resistance and exercise adaptations in skeletal muscle might be a cause, or consequence...

  9. Colloidal-based additive manufacturing of bio-inspired composites

    Science.gov (United States)

    Studart, Andre R.

    Composite materials in nature exhibit heterogeneous architectures that are tuned to fulfill the functional demands of the surrounding environment. Examples range from the cellulose-based organic structure of plants to highly mineralized collagen-based skeletal parts like bone and teeth. Because they are often utilized to combine opposing properties such as strength and low-density or stiffness and wear resistance, the heterogeneous architecture of natural materials can potentially address several of the technical limitations of artificial homogeneous composites. However, current man-made manufacturing technologies do not allow for the level of composition and fiber orientation control found in natural heterogeneous systems. In this talk, I will present two additive manufacturing technologies recently developed in our group to build composites with exquisite architectures only rivaled by structures made by living organisms in nature. Since the proposed techniques utilize colloidal suspensions as feedstock, understanding the physics underlying the stability, assembly and rheology of the printing inks is key to predict and control the architecture of manufactured parts. Our results will show that additive manufacturing routes offer a new exciting pathway for the fabrication of biologically-inspired composite materials with unprecedented architectures and functionalities.

  10. Natural and archaeological analogues: a review

    International Nuclear Information System (INIS)

    Brookins, D.G.

    1987-01-01

    In this chapter natural analogues in the geomedia for various aspects of radioactive waste disposal are discussed. Particular reference is made to the Okla Natural Reactor in Gabon. Igneous contact zones are discussed and natural analogues of waste-form materials. The importance of archaeological remains and anthropogenic materials left by man, in assessing weathering conditions and serving as radioactive waste analogues, is also emphasised. (UK)

  11. Clay Bells: Edo Inspiration

    Science.gov (United States)

    Wagner, Tom

    2010-01-01

    The ceremonial copper and iron bells at the Smithsonian's National Museum of African Art were the author's inspiration for an interdisciplinary unit with a focus on the contributions various cultures make toward the richness of a community. The author of this article describes an Edo bell-inspired ceramic project incorporating slab-building…

  12. Bio-inspired computation in telecommunications

    CERN Document Server

    Yang, Xin-She; Ting, TO

    2015-01-01

    Bio-inspired computation, especially those based on swarm intelligence, has become increasingly popular in the last decade. Bio-Inspired Computation in Telecommunications reviews the latest developments in bio-inspired computation from both theory and application as they relate to telecommunications and image processing, providing a complete resource that analyzes and discusses the latest and future trends in research directions. Written by recognized experts, this is a must-have guide for researchers, telecommunication engineers, computer scientists and PhD students.

  13. Colonial Agro-Industrialism : Science, Industry and the State in the Dutch Golden Alkaloid Age, 1850-1950

    NARCIS (Netherlands)

    Roersch van der Hoogte, A.

    2015-01-01

    This thesis is about what I call the Dutch Golden Alkaloid Age between roughly the 1850s and 1950s. I follow the historical trajectory of the production and distribution of the anti-febrifuge cinchona bark tree (Cinchona officinalis Lin.) and its most powerful and therapeutically applied alkaloid in

  14. Skeletal surveys in multiple myeloma

    International Nuclear Information System (INIS)

    Sebes, J.I.; Niell, H.B.; Palmieri, G.M.A.; Reidy, T.J.

    1986-01-01

    Thirty-three patients with multiple myeloma were studied with serial skeletal surveys, serum immunoglobulin levels, and postabsorptive urinary hydroxyproline (Spot-HYPRO) determinations. Twenty receiving chemotherapy were also followed with skeletal surveys in order to evaluate bone response to treatment. A close association was found between skeletal findings and changes in immunoglubulin levels with positive correlation in 71% of the patients. A similar association was found between skeletal disease and Spot-HYPRO level changes in 65%. Five of 12 patients (42%) with partial or complete clinical response to chemotherapy, demonstrated improvement in the appearance of skeletal lesions. Positive correlation between the roentgenographic changes and clinical markers of myeloma as well as therapeutic response, indicates that skeletal surveys are useful and effective in monitoring patients with multiple myeloma. (orig.)

  15. Screening of Alkaloidal Fraction of Conium maculatum L. Aerial Parts for Analgesic and Antiinflammatory Activity.

    Science.gov (United States)

    Madaan, Reecha; Kumar, S

    2012-09-01

    Conium maculatum Linn. (Umbelliferae) has been traditionally used in the treatment of spasmodic disorders, and to relieve nervous excitation, rheumatic pains in the old and feeble, pain in stomach, pain of gastric ulcer, nervousness and restlessness. Alkaloids have long been considered as bioactive group of constituents present in C. maculatum. Despite a long tradition of use, C. maculatum has not been evaluated pharmacologically to validate its traditional claims for analgesic and antiinflammatory activities. Thus, the present investigations were undertaken with an objective to evaluate alkaloidal fraction of C. maculatum aerial parts for analgesic and antiinflammatory activities. Test doses (100 or 200 mg/kg, p.o.) of alkaloidal fraction were evaluated for analgesic activity using tail flick test and antiinflammatory activity using carrageenan-induced paw oedema test in rats. Morphine (5 mg/kg, p.o.) and indomethacin (5 mg/kg, p.o.) were used as standard analgesic and antiinflammatory drugs, respectively. Alkaloidal fraction of the plant exhibited significant analgesic activity at a dose of 200 mg/kg as it showed significant increase in tail flicking reaction time with respect to the control during 2 h intervals of observation. It also exhibited significant antiinflammatory activity at a dose of 200 mg/kg as it inhibited paw oedema in rats to 71% and reduced the paw volume one-fourth to the control during 1(st) h of the study. The present investigations suggest that alkaloids are responsible for analgesic and antiinflammatory activities of C. maculatum.

  16. A survey of Senecio spp. affecting livestock in Uruguay and their associated pyrrolizidine alkaloid content

    Directory of Open Access Journals (Sweden)

    Juan Agustín García

    2018-02-01

    Full Text Available ABSTRACT: In Eastern Uruguay there has been a significant increase of seneciosis in grazing livestock with most affected localities related to counties neighboring the Brazilian border. A survey in 28 farms associated with poisoning outbreaks in grazing cattle in Eastern Uruguay was carried out. Fifty populations of Senecio plants were collected for alkaloid analysis and species identification. Four species were identified: S. oxyphyllus DC, S. madagascariensis Poir, S. brasiliensis (Spreng. Less., and S. selloi DC. Alkaloids were identified by a combination of GC-MS and HPLC-MS analysis and included: retrorsine in S. oxyphyllus; retrorsine, usaramine, and senecivernine/senecionine in S. selloi; retrorsine, senecivernine/senecionine, integerrimine, and usaramine in S. madagascariensis; and integerrimine, retrorsine and senecionine in S. brasiliensis. Total mean alkaloid concentration was reported to be highest in S. brasiliensis (17.6mg/g followed by S. oxyphyllus (6.2mg/g, S. selloi (1.8mg/g and S. madagascariensis (0.6mg/g. Alkaloid concentrations were also reported to be higher in 2015 vs. 2016 probably due to a common environmental factor. The species S. oxyphyllus and S. madagascariensis were not previously recognized as toxic plants in Eastern Uruguay. Particularly, S. oxyphyllus was present in 82% of the farms surveyed and occurred in high density with relative high concentrations of pyrrolizidine alkaloids suggesting S. oxyphyllus may be the main species involved in the reported outbreaks of seneciosis.

  17. Evolutionary recruitment of a flavin-dependent monooxygenase for stabilization of sequestered pyrrolizidine alkaloids in arctiids.

    Science.gov (United States)

    Langel, Dorothee; Ober, Dietrich

    2011-09-01

    Pyrrolizidine alkaloids are secondary metabolites that are produced by certain plants as a chemical defense against herbivores. They represent a promising system to study the evolution of pathways in plant secondary metabolism. Recently, a specific gene of this pathway has been shown to have originated by duplication of a gene involved in primary metabolism followed by diversification and optimization for its specific function in the defense machinery of these plants. Furthermore, pyrrolizidine alkaloids are one of the best-studied examples of a plant defense system that has been recruited by several insect lineages for their own chemical defense. In each case, this recruitment requires sophisticated mechanisms of adaptations, e.g., efficient excretion, transport, suppression of toxification, or detoxification. In this review, we briefly summarize detoxification mechanism known for pyrrolizidine alkaloids and focus on pyrrolizidine alkaloid N-oxidation as one of the mechanisms allowing insects to accumulate the sequestered toxins in an inactivated protoxic form. Recent research into the evolution of pyrrolizidine alkaloid N-oxygenases of adapted arctiid moths (Lepidoptera) has shown that this enzyme originated by the duplication of a gene encoding a flavin-dependent monooxygenase of unknown function early in the arctiid lineage. The available data suggest several similarities in the molecular evolution of this adaptation strategy of insects to the mechanisms described previously for the evolution of the respective pathway in plants. Copyright © 2011 Elsevier Ltd. All rights reserved.

  18. Chemometric approach for development, optimization, and validation of different chromatographic methods for separation of opium alkaloids.

    Science.gov (United States)

    Acevska, J; Stefkov, G; Petkovska, R; Kulevanova, S; Dimitrovska, A

    2012-05-01

    The excessive and continuously growing interest in the simultaneous determination of poppy alkaloids imposes the development and optimization of convenient high-throughput methods for the assessment of the qualitative and quantitative profile of alkaloids in poppy straw. Systematic optimization of two chromatographic methods (gas chromatography (GC)/flame ionization detector (FID)/mass spectrometry (MS) and reversed-phase (RP)-high-performance liquid chromatography (HPLC)/diode array detector (DAD)) for the separation of alkaloids from Papaver somniferum L. (Papaveraceae) was carried out. The effects of various conditions on the predefined chromatographic descriptors were investigated using chemometrics. A full factorial linear design of experiments for determining the relationship between chromatographic conditions and the retention behavior of the analytes was used. Central composite circumscribed design was utilized for the final method optimization. By conducting the optimization of the methods in very rational manner, a great deal of excessive and unproductive laboratory research work was avoided. The developed chromatographic methods were validated and compared in line with the resolving power, sensitivity, accuracy, speed, cost, ecological aspects, and compatibility with the poppy straw extraction procedure. The separation of the opium alkaloids using the GC/FID/MS method was achieved within 10 min, avoiding any derivatization step. This method has a stronger resolving power, shorter analysis time, better cost/effectiveness factor than the RP-HPLC/DAD method and is in line with the "green trend" of the analysis. The RP-HPLC/DAD method on the other hand displayed better sensitivity for all tested alkaloids. The proposed methods provide both fast screening and an accurate content assessment of the six alkaloids in the poppy samples obtained from the selection program of Papaver strains.

  19. Inhibition of hematopoietic prostaglandin D2 synthase (H-PGDS) by an alkaloid extract from Combretum molle.

    Science.gov (United States)

    Moyo, Rejoice; Chimponda, Theresa; Mukanganyama, Stanley

    2014-07-05

    Hematopoietic prostaglandin D2 synthase (H-PGDS, GST Sigma) is a member of the glutathione S-transferase super family of enzymes that catalyses the conjugation of electrophilic substances with reduced glutathione. The enzyme catalyses the conversion of PGH2 to PGD2 which mediates inflammatory responses. The inhibition of H-PGDS is of importance in alleviating damage to tissues due to unwarranted synthesis of PGD2. Combretum molle has been used in African ethno medicinal practices and has been shown to reduce fever and pain. The effect of C. molle alkaloid extract on H-PGDS was thus, investigated. H-PGDS was expressed in Escherichia coli XL1-Blue cells and purified using nickel immobilized metal affinity chromatography. The effect of C. molle alkaloid extract on H-PGDS activity was determined with 1-chloro-2, 4-dinitrobenzene (CDNB) as substrate. The effect of C. molle alkaloid extract with time on H-PGDS was determined. The mechanism of inhibition was then investigated using CDNB and glutathione (GSH) as substrates. A specific activity of 24 μmol/mg/min was obtained after H-PGDS had been purified. The alkaloid extract exhibited a 70% inhibition on H-PGDS with an IC50 of 13.7 μg/ml. C. molle alkaloid extract showed an uncompetitive inhibition of H-PGDS with Ki = 41 μg/ml towards GSH, and non-competitive inhibition towards CDNB with Ki = 7.7 μg/ml and Ki' = 9.2 μg/ml. The data shows that C. molle alkaloid extract is a potent inhibitor of H-PGDS. This study thus supports the traditional use of the plant for inflammation.

  20. Geissoschizine methyl ether N-oxide, a new alkaloid with antiacetylcholinesterase activity from Uncaria rhynchophylla.

    Science.gov (United States)

    Jiang, Wei-Wei; Su, Jia; Wu, Xing-De; He, Juan; Peng, Li-Yan; Cheng, Xiao; Zhao, Qin-Shi

    2015-01-01

    Geissoschizine methyl ether N-oxide, a new oxindole alkaloid, along with 14 known alkaloids, was isolated from the aerial part of Uncaria rhynchophylla. Their structures were identified by comprehensive spectral methods, including 2D NMR experiments, and confirmed by comparing with the literature data. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that the new compound exhibited anti-AChE activity with IC₅₀ value of 23.4 μM.

  1. INSPIRE 2012 da Istanbul a Firenze

    Directory of Open Access Journals (Sweden)

    Mauro Salvemini

    2012-09-01

    Full Text Available DURING THE CONFERENCE HELD IN  ISTANBUL IN  2012 INSPIRE  THE  NEWS  THAT  MOST  IMPRESSED ITALIANS PRESENT,  EVEN THOSE IN THE PUBLIC ADMINISTRATION , WAS THAT THE NEXT  INSPIRE CONFERENCE WILL TAKE PLACE IN  FLORENCEDurante la conferenza INSPIRE 2012 svoltasi ad Istanbul la notizia che ha maggiormente colpito gli italiani presenti, anche quelli della pubblica amministrazione , è stata che la prossima Conferenza INSPIRE si svolgerà a Firenze dal 23 al 27 giugno 2013.

  2. INSPIRE 2012 da Istanbul a Firenze

    Directory of Open Access Journals (Sweden)

    Mauro Salvemini

    2012-09-01

    Full Text Available DURING THE CONFERENCE HELD IN  ISTANBUL IN  2012 INSPIRE  THE  NEWS  THAT  MOST  IMPRESSED ITALIANS PRESENT,  EVEN THOSE IN THE PUBLIC ADMINISTRATION , WAS THAT THE NEXT  INSPIRE CONFERENCE WILL TAKE PLACE IN  FLORENCE Durante la conferenza INSPIRE 2012 svoltasi ad Istanbul la notizia che ha maggiormente colpito gli italiani presenti, anche quelli della pubblica amministrazione , è stata che la prossima Conferenza INSPIRE si svolgerà a Firenze dal 23 al 27 giugno 2013.

  3. NAUCLEFOLININE: A NEW ALKALOID FROM THE ROOTS OF ...

    African Journals Online (AJOL)

    a

    NAUCLEFOLININE: A NEW ALKALOID FROM THE ROOTS OF. NAUCLEA LATIFOLIA. D. Ngnokam1*, J.F. Ayafor1, J.D. Connolly2 and J.M. Nuzillard3. 1Department of Chemistry, University of Dschang, Box 67 Dschang, Cameroon. 2Department of Organic Chemistry, University of Glasgow, Glasgow G12 8QQ, Scotland.

  4. The study of chemical composition and pharmacological action of the alkaloid from plants of Lycoris Herb

    Science.gov (United States)

    Ji, Y. B.; Wei, C.; Xin, G. S.

    2017-12-01

    Recently, studies on Lycoris type alkaloids received the attention of scholars home and abroad. Lycoris type contains lots of alkaloids, it can be divided into seven types according to its molecular structure, including Lycorine, Crinine, Galanthamine, Tazettine, Narciclasine, Lycorenine, Homolycorine and Montanine. Researches have shown that Lycoris type possess multiple phamocology activity, such as strong anti-tumor activity of human breast cancer cell (MCF-7), human leukemia cell(HL-60); and strong inhibition effect of flu virus, measles virus, polio virus and SARS virus; Besides, Lycorine type has strong anti-Acetylcholinesterase effect. In a word, Lycorine type, Lycoris type alkaloids carries multiple pharmacology effect and is a promising substance.

  5. Whole-body MRI in comparison to skeletal scintigraphy for detection of skeletal metastases in patients with solid tumors

    International Nuclear Information System (INIS)

    Ghanem, N.; Altehoefer, C.; Winterer, J.; Schaefer, O.; Bley, T.A.; Langer, M.; Kelly, T.; Moser, E.

    2004-01-01

    The aim of this study was to compare the diagnostic efficacy of whole-body magnetic resonance imaging (WB-MRI) as a new and rapid examination technique with skeletal scintigraphy for detection of skeletal metastases from solid tumors. In 129 patients with solid malignant tumors, WB-MRI was performed for individual comparison with skeletal scintigraphy. Examinations were performed with the innovative AngioSURF trademark rolling table with integrated phased array surface coil and coronary TIRM sequences for different body regions. The results for WB-MRI and skeletal scintigraphy were concordant in 81% of the cases, whereby both procedures excluded skeletal metastases in 43%. WB-MRI and skeletal scintigraphy demonstrated skeletal metastases in 38% of the cases, whereby WB-MRI provided more comprehensive findings in 45%. In 12% of the cases, skeletal scintigraphy was superior to WB-MRI and in 19% the findings were discordant, whereby WB-MRI detected skeletal metastases in 15 cases which had not been found on skeletal scintigraphy. In nine cases, skeletal scintigraphy was positive when the WB-MRI was negative. In 60% of the cases, WB-MRI evidenced tumor-associated findings. WB-MRI represents a promising new staging technique for detection of skeletal metastases, which is more sensitive in many cases than skeletal scintigraphy in detecting and assessing the extent of skeletal metastases - and tumor-associated findings that are relevant for treatment strategy. (orig.) [de

  6. Qualitative and quantitative analysis of an alkaloid fraction from Piper longum L. using ultra-high performance liquid chromatography-diode array detector-electrospray ionization mass spectrometry.

    Science.gov (United States)

    Li, Kuiyong; Fan, Yunpeng; Wang, Hui; Fu, Qing; Jin, Yu; Liang, Xinmiao

    2015-05-10

    In a previous research, an alkaloid fraction and 18 alkaloid compounds were prepared from Piper longum L. by series of purification process. In this paper, a qualitative and quantitative analysis method using ultra-high performance liquid chromatography-diode array detector-mass spectrometry (UHPLC-DAD-MS) was developed to evaluate the alkaloid fraction. Qualitative analysis of the alkaloid fraction was firstly completed by UHPLC-DAD method and 18 amide alkaloid compounds were identified. A further qualitative analysis of the alkaloid fraction was accomplished by UHPLC-MS/MS method. Another 25 amide alkaloids were identified according to their characteristic ions and neutral losses. At last, a quantitative method for the alkaloid fraction was established using four marker compounds including piperine, pipernonatine, guineensine and N-isobutyl-2E,4E-octadecadienamide. After the validation of this method, the contents of above four marker compounds in the alkaloid fraction were 57.5mg/g, 65.6mg/g, 17.7mg/g and 23.9mg/g, respectively. Moreover, the relative response factors of other three compounds to piperine were calculated. A comparative study between external standard quantification and relative response factor quantification proved no remarkable difference. UHPLC-DAD-MS method was demonstrated to be a powerful tool for the characterization of the alkaloid fraction from P. longum L. and the result proved that the quality of alkaloid fraction was efficiently improved after appropriate purification. Copyright © 2015. Published by Elsevier B.V.

  7. Uptake of plant-derived specific alkaloids allows males of a butterfly to copulate.

    Science.gov (United States)

    Honda, Keiichi; Matsumoto, Junya; Sasaki, Ken; Tsuruta, Yoshiaki; Honda, Yasuyuki

    2018-04-03

    Certain butterflies utilize plant-acquired alkaloids for their own chemical defense and/or for producing male sex pheromone; a trait known as pharmacophagy. Males of the danaine butterfly, Parantica sita, have been reported to ingest pyrrolizidine alkaloids (PAs) as adults to produce two PA-derived sex pheromone components, viz. danaidone (major) and 7R-hydroxydanaidal. We found, however, that not all PAs that can be precursors for the pheromone serve for mating success of males. Here we show that although the sex pheromone is regarded as a requisite for successful mating, uptake of specific PA(s) (lycopsamine-type PAs) is also imperative for the males to achieve copulation. The increase in the levels of two biogenic amines, octopamine and/or serotonin, in the brain and thoracic ganglia of males fed with specific PA(s) suggested that these alkaloids most likely enhance male mating activity. The results can present new evidence for the evolutionary provenance of pharmacophagous acquisition of PAs in PA-adapted insects.

  8. Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals.

    Science.gov (United States)

    Oksman-Caldentey, Kirsi-Marja

    2007-08-01

    Many plants belonging to the Solanaceae family have been used as a source of pharmaceuticals for centuries because of their active principles, tropane and nicotine alkaloids. Tropane alkaloids, atropine, hyoscyamine and scopolamine, are among the oldest drugs in medicine. On the other hand nicotine, the addictive agent in tobacco, has only recently gained attention as a backbone for novel potential alkaloids to be used for certain neurological diseases. The biotechnological production of alkaloids utilizing plant cells as hosts would be an attractive option. However, to date very little success in this field has been gained because of the lack of understanding how these compounds are synthesized in a plant cell. Metabolic engineering attempts have already shown that when the rate-limiting steps of the biosynthetic pathway are completely known and the respective genes cloned, the exact regulation towards desired medicinal products will be possible in the near future. The new functional genomics tools, which combine transcriptome and metabolome data, will create a platform to better understand a whole system and to engineer the complex plant biosynthetic pathways. With the help of this technology, it is not only possible to produce known plant metabolites more effectively but also to make arrays of new compounds in plants and cell cultures.

  9. Effect of Alkaloids Isolated from Phyllodium pulchellum on Monoamine Levels and Monoamine Oxidase Activity in Rat Brain.

    Science.gov (United States)

    Cai, Lu; Wang, Chao; Huo, Xiao-Kui; Dong, Pei-Pei; Zhang, Bao-Jing; Zhang, Hou-Li; Huang, Shan-Shan; Zhang, Bo; Yu, Sheng-Ming; Zhong, Ming; Ma, Xiao-Chi

    2016-01-01

    Phyllodium pulchellum (P. pulchellum) is a folk medicine with a significant number of bioactivities. The aim of this study was to investigate the effects displayed by alkaloids fractions, isolated from the roots of P. pulchellum, on neurotransmitters monoamine levels and on monoamine oxidase (MAO) activity. Six alkaloids, which had indolealkylamine or β-carboline skeleton, were obtained by chromatographic technologies and identified by spectroscopic methods such as NMR and MS. After treatment with alkaloids of P. pulchellum, the reduction of DA levels (54.55%) and 5-HT levels (35.01%) in rat brain was observed by HPLC-FLD. The effect of alkaloids on the monoamines metabolism was mainly related to MAO inhibition, characterized by IC50 values of 37.35 ± 6.41 and 126.53 ± 5.39 μg/mL for MAO-A and MAO-B, respectively. The acute toxicity indicated that P. pulchellum extract was nontoxic.

  10. Perceptually-Inspired Computing

    Directory of Open Access Journals (Sweden)

    Ming Lin

    2015-08-01

    Full Text Available Human sensory systems allow individuals to see, hear, touch, and interact with the surrounding physical environment. Understanding human perception and its limit enables us to better exploit the psychophysics of human perceptual systems to design more efficient, adaptive algorithms and develop perceptually-inspired computational models. In this talk, I will survey some of recent efforts on perceptually-inspired computing with applications to crowd simulation and multimodal interaction. In particular, I will present data-driven personality modeling based on the results of user studies, example-guided physics-based sound synthesis using auditory perception, as well as perceptually-inspired simplification for multimodal interaction. These perceptually guided principles can be used to accelerating multi-modal interaction and visual computing, thereby creating more natural human-computer interaction and providing more immersive experiences. I will also present their use in interactive applications for entertainment, such as video games, computer animation, and shared social experience. I will conclude by discussing possible future research directions.

  11. Macrophage activating activity of pyrrole alkaloids from Morus alba fruits.

    Science.gov (United States)

    Kim, Seon Beom; Chang, Bo Yoon; Jo, Yang Hee; Lee, Sang Hoon; Han, Sang-Bae; Hwang, Bang Yeon; Kim, Sung Yeon; Lee, Mi Kyeong

    2013-01-09

    The fruits of Morus alba have been traditionally used as a tonic to enhance immune responses. The macrophage activating constituents of Morus alba fruits were purified using various column chromatography techniques. The structures of isolated compounds were determined on the basis of spectroscopic data interpretation such as 1D and 2D NMR analysis. The macrophage activating activities of isolated compounds were evaluated by measuring the production of nitric oxide, TNF-α and IL-12 in RAW 264.7 cells. The phagocytic activity was also evaluated. Five pyrrole alkaloids, 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (1), 2-formyl-1H-pyrrole-1-butanoic acid (2), 2-formyl-5-(hydroxymethyl)-1H-pyrrole-1-butanoic acid (3), 2-formyl-5-(methoxymethyl)-1H-pyrrole-1-butanoic acid (4) and Morrole A (5) were isolated from the fruits of Morus alba. Morrole A (5) is first reported in nature and other pyrrole alkaloids (1-4) are first reported from Morus species. Among the isolated compounds, compounds 3 and 4 significantly activated macrophage activity by the enhancement of nitric oxide, TNF-α and IL-12 production, and the stimulation of phagocytic activity in RAW 264.7 cells. Pyrrole alkaloids, including a new compound, were isolated from Morus alba fruits. These compounds activated macrophage activity in RAW 264.7 cells. Copyright © 2012 Elsevier Ireland Ltd. All rights reserved.

  12. Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids

    Directory of Open Access Journals (Sweden)

    Kettmann Viktor

    2007-07-01

    Full Text Available Abstract Roots and stem-bark of Mahonia aquifolium (Oregon grape (Berberidaceae are effectively used in the treatment of skin inflammatory conditions. In the present study, the effect of Mahonia aquifolium crude extract and its two representative alkaloid fractions containing protoberberine and bisbenzylisoquinoline (BBIQ alkaloids on activity of 12-lipoxygenase (12-LOX, was studied. The reactivity with 1,1-diphenyl-2-picryl-hydrazyl (DPPH, a free stable radical, was evaluated to elucidate the rate of possible lipid-derived radical scavenging in the mechanism of the enzyme inhibition. The results indicate that although the direct radical scavenging mechanism cannot be ruled out in the lipoxygenase inhibition by Mahonia aquifolium and its constituents, other mechanisms based on specific interaction between enzyme and alkaloids could play the critical role in the lipoxygenase inhibition rather than non-specific reactivity with free radicals.

  13. Nostalgia-Evoked Inspiration: Mediating Mechanisms and Motivational Implications.

    Science.gov (United States)

    Stephan, Elena; Sedikides, Constantine; Wildschut, Tim; Cheung, Wing-Yee; Routledge, Clay; Arndt, Jamie

    2015-10-01

    Six studies examined the nostalgia-inspiration link and its motivational implications. In Study 1, nostalgia proneness was positively associated with inspiration frequency and intensity. In Studies 2 and 3, the recollection of nostalgic (vs. ordinary) experiences increased both general inspiration and specific inspiration to engage in exploratory activities. In Study 4, serial mediational analyses supported a model in which nostalgia increases social connectedness, which subsequently fosters self-esteem, which then boosts inspiration. In Study 5, a rigorous evaluation of this serial mediational model (with a novel nostalgia induction controlling for positive affect) reinforced the idea that nostalgia-elicited social connectedness increases self-esteem, which then heightens inspiration. Study 6 extended the serial mediational model by demonstrating that nostalgia-evoked inspiration predicts goal pursuit (intentions to pursue an important goal). Nostalgia spawns inspiration via social connectedness and attendant self-esteem. In turn, nostalgia-evoked inspiration bolsters motivation. © 2015 by the Society for Personality and Social Psychology, Inc.

  14. Mechanistic Insights to the Cytotoxicity of Amaryllidaceae Alkaloids

    Czech Academy of Sciences Publication Activity Database

    Nair, J. J.; Rárová, L.; Strnad, Miroslav; Bastida, J.; van Staden, J.

    2015-01-01

    Roč. 10, č. 1 (2015), s. 171-182 ISSN 1934-578X Grant - others:GA MŠk(CZ) ED0007/01/01 Program:ED Institutional support: RVO:61389030 Keywords : Alkaloid * Amaryllidaceae * Apoptosis Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 0.884, year: 2015 http://www.ncbi.nlm.nih.gov/pubmed/25920242

  15. Quantification of alkaloids, phenols and flavonoids in sunflower ...

    African Journals Online (AJOL)

    Allelochemicals in leaves, stems and roots of sunflower (cv Hysun 38) were determined using thin layer chromatography (TLC) for alkaloids and spectrophotometry for phenols and flavonoids. In the TLC, the highest Rf value was recorded in leaves, followed by roots and stems, a sequence that held true also for the quantity ...

  16. Three new alkaloids from the fruits of Morus alba.

    Science.gov (United States)

    Wang, Xin; Kang, Jie; Wang, Hong-Qing; Liu, Chao; Li, Bao-Ming; Chen, Ruo-Yun

    2014-01-01

    From the fruits of Morus alba, three new alkaloids, mulbaines A (1), B (2), and C (3) were isolated. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HR-ESI-MS, 1D, and 2D NMR).

  17. Effect of inspiration on airway dimensions measured in maximal inspiration CT images of subjects without airflow limitation

    DEFF Research Database (Denmark)

    Petersen, Jens; Wille, Mathilde M.W.; Raket, Lars Lau

    2014-01-01

    . Automated software was utilized to segment lungs and airways, identify segmental bronchi, and match airway branches in all images of the same subject. Inspiration level was defined as segmented total lung volume (TLV) divided by predicted total lung capacity (pTLC). Mixed-effects models were used to predict......OBJECTIVES: To study the effect of inspiration on airway dimensions measured in voluntary inspiration breath-hold examinations. METHODS: 961 subjects with normal spirometry were selected from the Danish Lung Cancer Screening Trial. Subjects were examined annually for five years with low-dose CT...... • The effect of inspiration is greater in higher-generation (more peripheral) airways • Airways of generation 5 and beyond are as distensible as lung parenchyma • Airway dimensions measured from CT should be adjusted for inspiration level....

  18. Distribution coefficients of purine alkaloids in water-ammonium sulfate-alkyl acetate-dialkyl phthalate systems

    Science.gov (United States)

    Korenman, Ya. I.; Krivosheeva, O. A.; Mokshina, N. Ya.

    2012-12-01

    The distribution of purine alkaloids (caffeine, theobromine, theophylline) was studied in the systems: alkyl acetates-dialkyl phtalate-salting-out agent (ammonium sulfate). The quantitative characteristics of the extraction-distribution coefficients ( D) and the degree of extraction ( R, %) are calculated. The relationships between the distribution coefficients of alkaloids and the length of the hydrocarbon radical in the molecule of alkyl acetate (dialkyl phtalate) are determined. The possibility of predicting the distribution coefficients is demonstrated.

  19. [Contents mensuration of total alkaloid in Uncaria rhynchophylla by acid dye colorimetry].

    Science.gov (United States)

    Zeng, Chang-qing; Luo, Bei-liang

    2007-08-01

    To investigate the method of determination of total alkaloids Uncaria rhynchophylla. The Contents of total Alkaloid were determined by Acid dye Colorimetry. Acid dye color conditions: pH3.6 buffer 5.0 ml, bromocresol green liquid 5.0 ml; chloroform extraction three times, each time was exeracted for 2 minutes, put it aside for at least 5 minutes for the determination of the best method. Rhynchophylline 6.018 microg - 108.324 microg in the linear range, Recoveriys rate was 97.19%, RSD was 1.34% (n = 6). The method is simple, highly sensitive and reproducible.

  20. Teratogenic effects in cattle of Conium maculatum and conium alkaloids and analogs.

    Science.gov (United States)

    Keeler, R F; Balls, L D

    1978-01-01

    The plant Conium maculatum produced congenital defects in calves born to cows gavaged the fresh green plant during days 50-75 of gestation. Both arthrogryposis and spinal curvature were produced and were similar to the defects produced by the piperidine alkaloid coniine. The arthrogrypotic manifestations of the condition markedly increased in severity as the animals aged. Animals gavaged dry plant had either normal or equivocally deformed offspring. A number of chain length and ring saturation analogs of coniine were not teratogenic. No congenital defects arose in offspring from maternal inhalation of either the teratogenic alkaloid coniine, or from the teratogenic green plant.

  1. Nectar alkaloids decrease pollination and female reproduction in a native plant.

    Science.gov (United States)

    Adler, Lynn S; Irwin, Rebecca E

    2012-04-01

    The evolution of floral traits may be shaped by a community of floral visitors that affect plant fitness, including pollinators and floral antagonists. The role of nectar in attracting pollinators has been extensively studied, but its effects on floral antagonists are less understood. Furthermore, the composition of non-sugar nectar components, such as secondary compounds, may affect plant reproduction via changes in both pollinator and floral antagonist behavior. We manipulated the nectar alkaloid gelsemine in wild plants of the native perennial vine Gelsemium sempervirens. We crossed nectar gelsemine manipulations with a hand-pollination treatment, allowing us to determine the effect of both the trait and the interaction on plant female reproduction. We measured pollen deposition, pollen removal, and nectar robbing to assess whether gelsemine altered the behavior of mutualists and antagonists. High nectar gelsemine reduced conspecific pollen receipt by nearly half and also reduced the proportion of conspecific pollen grains received, but had no effect on nectar robbing. Although high nectar gelsemine reduced pollen removal, an estimate of male reproduction, by one-third, this effect was not statistically significant. Fruit set was limited by pollen receipt. However, this effect varied across sites such that the sites that were most pollen-limited were also the sites where nectar alkaloids had the least effect on pollen receipt, resulting in no significant effect of nectar alkaloids on fruit set. Finally, high nectar gelsemine significantly reduced seed weight; however, this effect was mediated by a mechanism other than pollen limitation. Taken together, our work suggests that nectar alkaloids are more costly than beneficial in our system, and that relatively small-scale spatial variation in trait effects and interactions could determine the selective impacts of traits such as nectar composition.

  2. Lyophilized skeletal imaging composition

    International Nuclear Information System (INIS)

    Vanduzee, B.F.

    1983-01-01

    This invention encompasses a process for producing a dry-powder skeletal imaging kit. An aqueous solution of a diphosphonate, a stannous reductant, and, optionally, a stabilizer is prepared. The solution is adjusted to a pH within the range 4.2 to 4.8 and the pH-adjusted solution is then lyophilized. The adjustment of pH, within a particular range, during the process of manufacturing lyophilized diphosphonate containing skeletal imaging kits yields a kit which produces a technetium skeletal imaging agent with superior imaging properties. This improved performance is manifested through faster blood clearance and higher skeletal uptake of the technetium imaging agent

  3. Discorhabdin alkaloids from Antarctic Latrunculia spp. sponges as a new class of cholinesterase inhibitors.

    Science.gov (United States)

    Botić, Tanja; Defant, Andrea; Zanini, Pietro; Žužek, Monika Cecilija; Frangež, Robert; Janussen, Dorte; Kersken, Daniel; Knez, Željko; Mancini, Ines; Sepčić, Kristina

    2017-08-18

    The brominated pyrroloiminoquinone alkaloids discorhabdins B, L and G and 3-dihydro-7,8- dehydrodiscorhabdin C, isolated from methanol extracts of two specimens of Latrunculia sp. sponges collected near the Antarctic Peninsula, are here demonstrated for the first time to be reversible competitive inhibitors of cholinesterases. They showed K i for electric eel acetylcholinesterase of 1.6-15.0 μM, for recombinant human acetylcholinesterase of 22.8-98.0 μM, and for horse serum butyrylcholinesterase of 5.0-76.0 μM. These values are promising when compared to the current cholinesterase inhibitors used for treatment of patients with Alzheimer's disease, to counteract the acetylcholine deficiency in the brain. Good correlation was obtained between IC 50 data and results by molecular docking calculation on the binding interactions within the acetylcholinesterase active site, which also indicated the moieties in discorhabdin structures involved. To avoid unwanted peripheral side effects that can appear in patients using some acetylcholinesterase inhibitors, electrophysiological experiments were carried out on one of the most active of these compounds, discorhabdin G, which confirmed that it had no detectable undesirable effects on neuromuscular transmission and skeletal muscle function. These findings are promising for development of cholinesterase inhibitors based on the scaffold of discorhabdins, as potential new agents for treatment of patients with Alzheimer's disease. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  4. Neurotoxic Alkaloids: Saxitoxin and Its Analogs

    Directory of Open Access Journals (Sweden)

    Troco K. Mihali

    2010-07-01

    Full Text Available Saxitoxin (STX and its 57 analogs are a broad group of natural neurotoxic alkaloids, commonly known as the paralytic shellfish toxins (PSTs. PSTs are the causative agents of paralytic shellfish poisoning (PSP and are mostly associated with marine dinoflagellates (eukaryotes and freshwater cyanobacteria (prokaryotes, which form extensive blooms around the world. PST producing dinoflagellates belong to the genera Alexandrium, Gymnodinium and Pyrodinium whilst production has been identified in several cyanobacterial genera including Anabaena, Cylindrospermopsis, Aphanizomenon Planktothrix and Lyngbya. STX and its analogs can be structurally classified into several classes such as non-sulfated, mono-sulfated, di-sulfated, decarbamoylated and the recently discovered hydrophobic analogs—each with varying levels of toxicity. Biotransformation of the PSTs into other PST analogs has been identified within marine invertebrates, humans and bacteria. An improved understanding of PST transformation into less toxic analogs and degradation, both chemically or enzymatically, will be important for the development of methods for the detoxification of contaminated water supplies and of shellfish destined for consumption. Some PSTs also have demonstrated pharmaceutical potential as a long-term anesthetic in the treatment of anal fissures and for chronic tension-type headache. The recent elucidation of the saxitoxin biosynthetic gene cluster in cyanobacteria and the identification of new PST analogs will present opportunities to further explore the pharmaceutical potential of these intriguing alkaloids.

  5. Molluscicidal activity of Hammada scoparia (Pomel Iljin leaf extracts and the principal alkaloids isolated from them against Galba truncatula

    Directory of Open Access Journals (Sweden)

    R Mezghani-Jarraya

    2009-11-01

    Full Text Available The molluscicidal activity of Hammada scoparia leaf extracts and the principal alkaloids isolated from them (carnegine and N-methylisosalsoline were tested against the mollusc gastropod, Galba truncatula, the intermediate host of Fasciola hepatica in Tunisia. The results indicated that the molluscicidal activity was correlated with the presence of alkaloids. A significant molluscicidal value, according to the World Health Organization, was found with the methanol extract (LC50 = 28.93 ppm. Further fractionation of the methanolic extract led to the isolation of two principal alkaloids: carnegine and N-methylisosalsoline. These alkaloids are isoquinolines that have not previously been characterised for their molluscicidal activity. The N-methylisosalsoline possesses the highest molluscicidal activity (LC50 = 0.47 μM against G. truncatula.

  6. Influence of 7,8-methylenedioxylycoctonine-type alkaloids on the toxic effects associated with ingestion of tall larkspur (Delphinium spp) in cattle.

    Science.gov (United States)

    Welch, Kevin D; Green, Benedict T; Gardner, Dale R; Cook, Daniel; Pfister, James A; Stegelmeier, Bryan L; Panter, Kip E; Davis, T Zane

    2010-04-01

    To determine the contribution of 7,8-methylenedioxylycoctonine (MDL)-type alkaloids to the toxic effects of tall larkspur (Delphinium spp) consumption in cattle. Sixteen 2-year-old Angus steers. Plant material from 3 populations of tall larkspur that contained different concentration ratios of MDL-type-to-N-(methylsuccinimido) anthranoyllycoctonine (MSAL)-type alkaloids was collected, dried, and finely ground. For each plant population, a dose of ground plant material that would elicit similar clinical signs of toxicosis in cattle after oral administration was determined on the basis of the plants' MSAL-type alkaloid concentration. Cattle were treated via oral gavage with single doses of ground plant material from each of the 3 populations of tall larkspur; each animal underwent 1 to 3 single-dose treatments (> or = 21-day interval between treatments). Heart rate was recorded immediately before (baseline) and 24 hours after each larkspur treatment. Tall larkspur populations with a lower MDL-type-to-MSAL-type alkaloid concentration ratio required a greater amount of MSAL-type alkaloids to cause the expected clinical signs of toxicosis (including increased heart rate) in cattle. Results indicated that the typically less toxic MDL-type alkaloids contributed in a significant manner to the toxic effects of tall larkspur in steers. Consequently, both the concentration of MSAL-type alkaloids and the total concentration of MSAL- and MDL-type alkaloids should be determined when assessing the relative toxicity of tall larkspur populations. These results provide valuable information to determine the risk of toxicosis in cattle grazing on tall larkspur-infested rangelands.

  7. A Short Term Analogue Memory

    DEFF Research Database (Denmark)

    Shah, Peter Jivan

    1992-01-01

    A short term analogue memory is described. It is based on a well-known sample-hold topology in which leakage currents have been minimized partly by circuit design and partly by layout techniques. Measurements on a test chip implemented in a standard 2.4 micron analogue CMOS process show a droop...

  8. Skeletal imaging composition

    International Nuclear Information System (INIS)

    Vanduzee, B.F.; Degenhardt, C.R.

    1983-01-01

    This invention is based on the discovery that the adjustment of pH, within a particular range, during the process of manufacturing lyophilized diphosphonate-containing skeletal imaging kits yields a kit which produces a technetium skeletal imaging agent with superior imaging properties. This increased performance is manifested through faster blood clearance and higher skeletal uptake of the technetium imaging agent. The process for producing a dry-powder imaging kit comprises the steps of: preparing a solution of a diphosphonate carrier, stannous reductant, and a stabilizer in water; adjusting the pH to between 5.5 and 6.5; and lyophilizing the solution

  9. Pyrrolizidine Alkaloids from Onosmakaheirei Teppner (Boraginaceae

    Directory of Open Access Journals (Sweden)

    Ioanna Maria Orfanou

    2016-03-01

    Full Text Available The new pyrrolizidine alkaloid (PA 3΄-O-acetylechinatine N-oxide (7, along with two more known PAs (5, 6, two known flavonoids (3, 4, one known alkannin (1, two known triterpenoids, one known sterol, and allantoin (2 were isolated from the aerial parts of Onosma kaheirei. In addition, the retention indeces of the reduced PAs 6 and 7 were determined in a DB-5 WCOT column, to aid their detection by GC/MS in the future.

  10. The anti-inflammation and pharmacokinetics of a novel alkaloid from Portulaca oleracea L.

    Science.gov (United States)

    Meng, Yihan; Ying, Zheming; Xiang, Zheng; Hao, Dong; Zhang, Wenjie; Zheng, Yu; Gao, Yucong; Ying, Xixiang

    2016-03-01

    This study was to elucidate the pharmacokinetics of a novel alkaloid, 6-acetyl-2,2,5-trimethyl-2,3-dihydrocyclohepta[b]pyrrol-8(1H)-one, named oleracone isolated from Portulaca oleracea L., and to examine the anti-inflammatory ability with lipopolysaccharide (LPS) stimulated macrophages. The novel alkaloid, oleracone, was isolated from Portulaca oleracea L., and its structure was determined by spectroscopic analysis including HRESIMS, 2D NMR spectroscopic data and single-crystal X-ray diffraction. The activity of anti-inflammation was assayed via the test with RAW 264.7 activated by LPS, and the pharmacokinetics of oleracone in rat plasma after intravenous and oral administration at dose of 2.5 mg/kg was, respectively, investigated by a rapid and sensitive ultra high-performance liquid chromatography (UHPLC) method with bergapten as internal standard. Oleracone was a novel alkaloid first isolated from Portulaca oleracea L. and possessed unique structure in natural products, whose anti-inflammatory effecting on nitrite oxide production and several pivotal pro-inflammatory cytokines was found at the concentration of 50 μm, and the pharmacokinetic results indicated that oleracone was rapidly distributed with Tmax of 15.7 min after oral administration and presented a higher oral absolute bioavailability to be 74.91 ± 10.7%. Oleracone as novel alkaloid presented remarkably anti-inflammatory effect, which was rapid distributed in rat with high bioavailability of 74.91 ± 10.7%. © 2016 Royal Pharmaceutical Society, Journal of Pharmacy and Pharmacology.

  11. Analogue to Digital and Digital to Analogue Converters (ADCs and DACs): A Review Update

    CERN Document Server

    Pickering, J.

    2015-06-15

    This is a review paper updated from that presented for CAS 2004. Essentially, since then, commercial components have continued to extend their performance boundaries but the basic building blocks and the techniques for choosing the best device and implementing it in a design have not changed. Analogue to digital and digital to analogue converters are crucial components in the continued drive to replace analogue circuitry with more controllable and less costly digital processing. This paper discusses the technologies available to perform in the likely measurement and control applications that arise within accelerators. It covers much of the terminology and 'specmanship' together with an application-oriented analysis of the realisable performance of the various types. Finally, some hints and warnings on system integration problems are given.

  12. Indole Alkaloids from the Sea Anemone Heteractis aurora and Homarine from Octopus cyanea.

    Science.gov (United States)

    Shaker, Kamel H; Göhl, Matthias; Müller, Tobias; Seifert, Karlheinz

    2015-11-01

    The two new indole alkaloids 2-amino-1,5-dihydro-5-(1H-indol-3-ylmethyl)-4H-imidazol-4-one (1), 2-amino-5-[(6-bromo-1H-indol-3-yl)methyl]-3,5-dihydro-3-methyl-4H-imidazol-4-one (2), and auramine (3) have been isolated from the sea anemone Heteractis aurora. Both indole alkaloids were synthesized for the confirmation of the structures. Homarine (4), along with uracil (5), hypoxanthine (6), and inosine (7) have been obtained from Octopus cyanea. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.

  13. Seedlings Of Ocotea puberula (Lauraceae): identification and monitoring of aporphinoid alkaloids; Mudas de Ocotea puberula (Lauraceae): identificacao e monitoramento de alcaloides aporfinoides

    Energy Technology Data Exchange (ETDEWEB)

    Zanin, Sandra Maria Warumby; Miguel, Obdulio Gomes; Montrucchio, Deise Prehs; Costa, Camila Klocker; Lagos, Jesse Boquett [Universidade Federal do Parana (UFPR), Curitiba, PR (Brazil). Dept. de Farmacia; Lordello, Ana Luisa Lacava, E-mail: lordello@ufpr.b [Universidade Federal do Parana (UFPR), Curitiba, PR (Brazil). Dept. de Quimica

    2011-10-26

    This work describes the occurrence and contents of aporphinoids alkaloids in seedlings of Ocotea puberula from germination until 12 months old and in leaves from adult plants. Seedling leaves showed an alkaloids profile similar to leaves of adult plant. However, leaves in seedlings showed higher contents of the alkaloids boldine, dicentrine, leucoxine and isodomesticine when compared to adult plants. The alkaloids concentration in stems and leaves increased during the development of the seedlings, followed by a remarkable decrease of these compounds in roots. Cultivation in a seedling-nursery method is also described. (author)

  14. Quantum analogue computing.

    Science.gov (United States)

    Kendon, Vivien M; Nemoto, Kae; Munro, William J

    2010-08-13

    We briefly review what a quantum computer is, what it promises to do for us and why it is so hard to build one. Among the first applications anticipated to bear fruit is the quantum simulation of quantum systems. While most quantum computation is an extension of classical digital computation, quantum simulation differs fundamentally in how the data are encoded in the quantum computer. To perform a quantum simulation, the Hilbert space of the system to be simulated is mapped directly onto the Hilbert space of the (logical) qubits in the quantum computer. This type of direct correspondence is how data are encoded in a classical analogue computer. There is no binary encoding, and increasing precision becomes exponentially costly: an extra bit of precision doubles the size of the computer. This has important consequences for both the precision and error-correction requirements of quantum simulation, and significant open questions remain about its practicality. It also means that the quantum version of analogue computers, continuous-variable quantum computers, becomes an equally efficient architecture for quantum simulation. Lessons from past use of classical analogue computers can help us to build better quantum simulators in future.

  15. Berbanine: a new isoquinoline-isoquinolone alkaloid from Berberis vulgaris (Berberidaceae)

    Czech Academy of Sciences Publication Activity Database

    Hošťálková, A.; Novák, Z.; Pour, M.; Jirošová, Anna; Opletal, L.; Kuneš, J.; Cahlíková, L.

    2013-01-01

    Roč. 8, č. 4 (2013), s. 441-442 ISSN 1934-578X Institutional support: RVO:61388963 Keywords : Berberis vulgaris * Berberidaceae * alkaloid * isoquinoline-isoquinolone dimer * berbanine Subject RIV: CC - Organic Chemistry Impact factor: 0.924, year: 2013

  16. Pyrrolizidine alkaloid toxicity in livestock: A paradigm for human poisoning

    Science.gov (United States)

    Livestock poisoning, primarily liver damage, caused by consumption of plants containing 1,2-dehydropyrro-lizidine ester alkaloids (dehydroPAs), and the corresponding N-oxides, is a relatively common occurrence worldwide. Because of the economic impact, extensive investigations...

  17. Diversity of the Mountain Flora of Central Asia with Emphasis on Alkaloid-Producing Plants

    Directory of Open Access Journals (Sweden)

    Karimjan Tayjanov

    2017-02-01

    Full Text Available The mountains of Central Asia with 70 large and small mountain ranges represent species-rich plant biodiversity hotspots. Major mountains include Saur, Tarbagatai, Dzungarian Alatau, Tien Shan, Pamir-Alai and Kopet Dag. Because a range of altitudinal belts exists, the region is characterized by high biological diversity at ecosystem, species and population levels. In addition, the contact between Asian and Mediterranean flora in Central Asia has created unique plant communities. More than 8100 plant species have been recorded for the territory of Central Asia; about 5000–6000 of them grow in the mountains. The aim of this review is to summarize all the available data from 1930 to date on alkaloid-containing plants of the Central Asian mountains. In Saur 301 of a total of 661 species, in Tarbagatai 487 out of 1195, in Dzungarian Alatau 699 out of 1080, in Tien Shan 1177 out of 3251, in Pamir-Alai 1165 out of 3422 and in Kopet Dag 438 out of 1942 species produce alkaloids. The review also tabulates the individual alkaloids which were detected in the plants from the Central Asian mountains. Quite a large number of the mountain plants produce neurotoxic and cytotoxic alkaloids, indicating that a strong chemical defense is needed under the adverse environmental conditions of these mountains with presumably high pressure from herbivores.

  18. [Pharmacokinetic study of six aconitine alkaloids in aconiti lateralis radix praeparata in beagle dogs].

    Science.gov (United States)

    Xiao, Ri-Ping; Lai, Xiao-Ping; Zhao, Yai; Yu, Liang-Wen; Zhu, Yue-Lan; Li, Geng

    2014-02-01

    To study the pharmacokinetics characteristics of six Aconitum alkaloids aconitine (AC), mesaconitine (MA), hypaconitine (HA), benzoylaconine (BAC), benzoylmesaconine (BMA) and benzoylhypaconine (BHA) in beagle dogs. An ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was developed for simultaneous quantitation of six Aconitum alkaloids in beagle dog plasma after oral administration of Aconiti Lateralis Radix Praeparata decoction. UPLC/MS/MS system coupled with an electrospray ionization (ESI) source was performed in multiple-reaction monitoring (MRM) mode. Sample preparation was performed with solid-phase extraction(SPE) on a 3 mL HLB cartridge before the analysis. The separation was applied on a Waters C8 column (100 mm x 2.1 mm, 1.7 microm) and a gradient elution of methanol and 0.2% formic acid-water was used as mobile phase. The pharmacokinetic parameters were calculated by the results of the analysis through the DAS 2. 1 software (Drug and Statistics for Windows). The results showed that the fitting model for the six Aconitum alkaloids was the one-compartment model pharmacokinetics. The method is successfully used for the pharmacokinetic evaluation of the six Aconitum alkaloids in beagle dog plasma, it can help monitor the ADME/Tox process when taking Aconiti Lateralis Radix Praeparata by observing the pharmacokinetic process. The results provide a good reference for clinical treatment and safe application of Aconiti Lateralis Radix Praeparata.

  19. Erythrina mulungu alkaloids are potent inhibitors of neuronal nicotinic receptor currents in mammalian cells.

    Directory of Open Access Journals (Sweden)

    Pedro Setti-Perdigão

    Full Text Available Crude extracts and three isolated alkaloids from Erythrina mulungu plants have shown anxiolytic effects in different animal models. We investigated whether these alkaloids could affect nicotinic acetylcholine receptors and if they are selective for different central nervous system (CNS subtypes. Screening experiments were performed using a single concentration of the alkaloid co-applied with acetylcholine in whole cell patch-clamp recordings in three different cell models: (i PC12 cells natively expressing α3* nicotinic acetylcholine receptors; (ii cultured hippocampal neurons natively expressing α7* nicotinic acetylcholine receptors; and (iii HEK 293 cells heterologoulsy expressing α4β2 nicotinic acetylcholine receptors. For all three receptors, the percent inhibition of acetylcholine-activated currents by (+-11á-hydroxyerysotrine was the lowest, whereas (+-erythravine and (+-11á-hydroxyerythravine inhibited the currents to a greater extent. For the latter two substances, we obtained concentration-response curves with a pre-application protocol for the α7* and α4β2 nicotinic acetylcholine receptors. The IC50 obtained with (+-erythravine and (+-11á-hydroxyerythravine were 6 µM and 5 µM for the α7* receptors, and 13 nM and 4 nM for the α4β2 receptors, respectively. Our data suggest that these Erythrina alkaloids may exert their behavioral effects through inhibition of CNS nicotinic acetylcholine receptors, particularly the α4β2 subtype.

  20. Developments in drug delivery of bioactive alkaloids derived from traditional Chinese medicine.

    Science.gov (United States)

    Zheng, Xiao; Wu, Fei; Lin, Xiao; Shen, Lan; Feng, Yi

    2018-11-01

    The bioactive alkaloids (e.g. vincristine, hydroxycamptothecin, ligustrazine, and so on) from traditional Chinese medicine (TCM) have exerted potent efficacies (e.g. anti-tumor, anti-inflammation, immunosuppression, etc.). However, a series of undesirable physicochemical properties (like low solubility and weak stability) and baneful pharmacokinetic (PK) profiles (e.g. low bioavailability, short half time, rapid clearance, etc.) have severely restricted their applications in clinic. In addition, some side effects (like cumulative toxicities caused by high-frequency administration and their own toxicities) have recently been reported and also confined their clinical uses. Therefore, developments in drug delivery of such alkaloids are of significance in improving their drug-like properties and, thus, treatment efficiencies in clinic. Strategies, including (i) specific delivery via liposomes; (ii) sustained delivery via nanoparticles, gels, and emulsions; and (iii) transdermal delivery via ethosomes, solid lipid nanoparticles, and penetrating enhancers, have been reported to improve the pharmacokinetic and physicochemical characters of problematic TCM alkaloids, decline their adverse effects, and thus, boost their curative efficacies. In this review, the recent reports in this field were comprehensively summarized with the aim of providing an informative reference for relevant readers.

  1. Inspiring a generation

    CERN Multimedia

    2012-01-01

    The motto of the 2012 Olympic and Paralympic Games is ‘Inspire a generation’ so it was particularly pleasing to see science, the LHC and Higgs bosons featuring so strongly in the opening ceremony of the Paralympics last week.   It’s a sign of just how far our field has come that such a high-profile event featured particle physics so strongly, and we can certainly add our support to that motto. If the legacy of London 2012 is a generation inspired by science as well as sport, then the games will have more than fulfilled their mission. Particle physics has truly inspiring stories to tell, going well beyond Higgs and the LHC, and the entire community has played its part in bringing the excitement of frontier research in particle physics to a wide audience. Nevertheless, we cannot rest on our laurels: maintaining the kind of enthusiasm for science we witnessed at the Paralympic opening ceremony will require constant vigilance, and creative thinking about ways to rea...

  2. In vitro androgenetic cultures of Hyoscyamus niger L., H. albus L. and alkaloid content assay

    Directory of Open Access Journals (Sweden)

    Maria Wesołwska

    2014-01-01

    Full Text Available In vitro cultures of Hyoscyamus niger L. and H. albus L. anthers were initiated which resulted in obtaining androgenectic plants and callus cultures. The leaves of these pants and the callus cultures were subjected to analysis (TLC, GC for the presence of alkaloids, derivatives of tropane. In the studied material, alkaloids of different qualitative and quantitative composition from that of ground-grown plants were found.

  3. Biosynthesis of tylophora alkaloids

    International Nuclear Information System (INIS)

    Mulchandani, N.B.; Iyer, S.S.; Badheka, L.P.

    1974-01-01

    Using labelled precursors, biosynthesis of the tylophora alkaloids, tylophorine, tylophorinidine and tylophorinide has been investigated in Tylophora asthmatica plants. The radioactive precursors, phenylalanine-2- 14 C, benzoic acid-1- 14 C, benzoic acid-ring 14 C, acetate-2- 14 C, ornithine-5- 14 C, acetate-2- 14 C, ornithine-5- 14 C and cinnamic acid-2- 14 C were administered to the plants individually by wick technique. Tylophorine was isolated in each case and assayed for its radioactivity to find out the incorporation of the label into it. The results indicate that: (1) phenylalanine via cinnamic acid is an important precursor in the biosynthesis of tylophorine (2) orinithine participates in tylophorine biosynthesis via pyrroline and (3) tylophorinidine may be a direct precursor of tylophorine. (M.G.B.)

  4. La maturità di INSPIRE

    Directory of Open Access Journals (Sweden)

    Mauro Salvemini

    2010-03-01

    Full Text Available INPIRE's maturityThe INSPIRE Conference 2010 took place from 23 to 25 June 2010 in Kraków, Poland. On 22 June pre-conference workshops have been organized. The theme of this year’s edition has been "INSPIRE as a Framework for Cooperation".The INSPIRE Conference has been organised through a series of plenary sessions addressing common policy issues, and parallel sessions focusing in particular on applications and implementations of SDIs, research issues and new and evolvingtechnologies and applications and poster presentations.

  5. An efficient and target-oriented sample enrichment method for preparative separation of minor alkaloids by pH-zone-refining counter-current chromatography.

    Science.gov (United States)

    Feng, Rui-Hong; Hou, Jin-Jun; Zhang, Yi-Bei; Pan, Hui-Qin; Yang, Wenzhi; Qi, Peng; Yao, Shuai; Cai, Lu-Ying; Yang, Min; Jiang, Bao-Hong; Liu, Xuan; Wu, Wan-Ying; Guo, De-An

    2015-08-28

    An efficient and target-oriented sample enrichment method was established to increase the content of the minor alkaloids in crude extract by using the corresponding two-phase solvent system applied in pH-zone-refining counter-current chromatography. The enrichment and separation of seven minor indole alkaloids from Uncaria rhynchophylla (Miq.) Miq. ex Havil(UR) were selected as an example to show the advantage of this method. An optimized two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (3:7:1:9, v/v) was used in this study, where triethylamine (TEA) as the retainer and hydrochloric acid (HCl) as the eluter were added at the equimolar of 10mM. Crude alkaloids of UR dissolved in the corresponding upper phase (containing 10mM TEA) were extracted twice with lower phase (containing 10mM TEA) and lower phase (containing 10mM HCl), respectively, the second lower phase extract was subjected to pH-zone-refining CCC separation after alkalization and desalination. Finally, from 10g of crude alkaloids, 4g of refined alkaloids was obtained and the total content of seven target indole alkaloids was increased from 4.64% to 15.78%. Seven indole alkaloids, including 54mg isocorynoxeine, 21mg corynoxeine, 46mg isorhynchophylline, 35mg rhynchophylline, 65mg hirsutine, 51mg hirsuteine and 27mg geissoschizine methylether were all simultaneously separated from 2.5g of refined alkaloids, with the purity of 86.4%, 97.5%, 90.3%, 92.1%, 98.5%, 92.3%, and 92.8%, respectively. The total content and purities of the seven minor indole alkaloids were tested by HPLC and their chemical structures were elucidated by ESI-HRMS and (1)H NMR. Copyright © 2015 Elsevier B.V. All rights reserved.

  6. Quinolizidines alkaloids: Petrosin and xestospongins from the sponge Oceanapia sp.

    Digital Repository Service at National Institute of Oceanography (India)

    Singh, K.S.; Das, B.; Naik, C.G.

    having di-hetro atom rings, from the ethyl acetate extract of the sponge. The compounds exhibited moderate to high activities against some microorganisms and clinical isolates. The structures of the alkaloids were elucidated by NMR and ESIMS spectroscopic...

  7. Caavuranamide, a novel steroidal alkaloid from the ripe fruits of Solanum caavurana Vell. (Solanaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Vaz, Nelissa Pacheco; Santos, Erica L.; Marques, Francisco A.; Maia, Beatriz H.L.N. Sales, E-mail: noronha@ufpr.br [Departamento de Quimica, Universidade Federal do Parana, Centro Politecnico, Curitiba, PR (Brazil); Costa, Emmanoel V. [Departamento de Quimica, Universidade Federal de Sergipe, Sao Cristovao, SE (Brazil); Mikich, Sandra Bos [Laboratorio de Ecologia, Embrapa Florestas, Colombo, PR (Brazil); Braga, Raquel M. [Instituto de Quimica, Universidade Estadual de Campinas, SP (Brazil); Delarmelina, Camila; Duarte, Marta C.T. [Divisao de Microbiologia, Centro Pluridisciplinar de Pesquisas Quimicas Biologicas e Agricolas (CPQBA), Universidade Estadual de Campinas, SP (Brazil); Duarte, Marta C.T.; Ruiz, Ana Lucia T.G.; Souza, Vanessa H.S.; Carvalho, Joao E. de [Divisa de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Quimicas Biologicas e Agricolas (CPQBA), Universidade Estadual de Campinas, SP (Brazil)

    2012-07-01

    Phytochemical investigation of the ripe fruits of Solanum caavurana Vell. (Solanaceae) afforded a novel steroidal alkaloid with spirosolane-type skeleton, named as caavuranamide, together with the alkaloids 4-tomatiden-3-one and 5{alpha}-tomatidan-3-one. Their structures were elucidated on the basis of spectroscopic methods. The antiproliferative and antimicrobial activities for the ethanolic extract, sub-fractions obtained from partition and acid-base treatment were also evaluated. Caavuranamide showed antibacterial activity similar to the chloramphenicol positive control against Rhodococcus equi. (author)

  8. Caavuranamide, a novel steroidal alkaloid from the ripe fruits of Solanum caavurana Vell. (Solanaceae)

    International Nuclear Information System (INIS)

    Vaz, Nelissa Pacheco; Santos, Erica L.; Marques, Francisco A.; Maia, Beatriz H.L.N. Sales; Costa, Emmanoel V.; Mikich, Sandra Bos; Braga, Raquel M.; Delarmelina, Camila; Duarte, Marta C.T.; Duarte, Marta C.T.; Ruiz, Ana Lucia T.G.; Souza, Vanessa H.S.; Carvalho, Joao E. de

    2012-01-01

    Phytochemical investigation of the ripe fruits of Solanum caavurana Vell. (Solanaceae) afforded a novel steroidal alkaloid with spirosolane-type skeleton, named as caavuranamide, together with the alkaloids 4-tomatiden-3-one and 5α-tomatidan-3-one. Their structures were elucidated on the basis of spectroscopic methods. The antiproliferative and antimicrobial activities for the ethanolic extract, sub-fractions obtained from partition and acid-base treatment were also evaluated. Caavuranamide showed antibacterial activity similar to the chloramphenicol positive control against Rhodococcus equi. (author)

  9. In silico Assessment of Drug-like Properties of Alkaloids from Areca ...

    African Journals Online (AJOL)

    service were used to predict the drug-like properties of the alkaloids, including ... International Pharmaceutical Abstract, Chemical Abstracts, Embase, Index Copernicus, EBSCO, African ..... estimate solubility and permeability in drug discovery.

  10. Double reductive cyclization: A facile synthesis of the indoloquinoline alkaloid cryptotackieine

    Digital Repository Service at National Institute of Oceanography (India)

    Parvatkar, P.T.; Parameswaran, P.S.; Tilve, S.G.

    A new synthesis of the indoloquinoline alkaloid cryptotackieine, isolated from Cryptolepis sanguinolenta, is described which involves a Perkin reaction, a tandem double reduction-double cyclization reaction followed by regioselective methylation...

  11. Comparative Study of Skeletal Stability between Postoperative Skeletal Intermaxillary Fixation and No Skeletal Fixation after Bilateral Sagittal Split Ramus Osteotomy

    DEFF Research Database (Denmark)

    Hartlev, Jens; Godtfredsen, Erik; Andersen, Niels Trolle

    2014-01-01

    OBJECTIVES: The purpose of the present study was to evaluate skeletal stability after mandibular advancement with bilateral sagittal split osteotomy. MATERIAL AND METHODS: Twenty-six patients underwent single-jaw bilateral sagittal split osteotomy (BSSO) to correct skeletal Class II malocclusion....

  12. Simultaneous determination of seven alkaloids from Rhizoma Corydalis Decumbentis in rabbit aqueous humor by LC-MS/MS: Application to ocular pharmacokinetic studies.

    Science.gov (United States)

    Mao, Zhengsheng; Wang, Xin; Liu, Yangdan; Huang, Yuting; Liu, Youping; Di, Xin

    2017-07-01

    This study aims to establish a fast and sensitive LC-MS/MS method for simultaneous determination of seven alkaloids from Rhizoma Corydalis Decumbentis in rabbit aqueous humor. Aqueous humor samples were processed by protein precipitation and then separated on a Thermo Syncronis C 18 column (50mm×2.1mm, 5μm) with a mobile phase using acetonitrile-0.05% formic acid (28:72, v/v). Detection of the analytes and the internal standard (coptisine) were performed in positive electrospray ionization with selected reaction monitoring. The method showed good linearity (r>0.9931) for all the seven alkaloids. This fully validated method was applied to the studies of aqueous humor pharmacokinetics of seven alkaloids from Rhizoma Corydalis Decumbentis and the effects of borneol on corneal penetration of these alkaloids into aqueous humor. This is the first work that presents a reliable LC-MS/MS method for simultaneous determination of seven alkaloids in rabbit aqueous humor and its application of ocular pharmacokinetics of seven alkaloids from Rhizoma Corydalis Decumbentis. Copyright © 2017 Elsevier B.V. All rights reserved.

  13. Nature-inspired optimization algorithms

    CERN Document Server

    Yang, Xin-She

    2014-01-01

    Nature-Inspired Optimization Algorithms provides a systematic introduction to all major nature-inspired algorithms for optimization. The book's unified approach, balancing algorithm introduction, theoretical background and practical implementation, complements extensive literature with well-chosen case studies to illustrate how these algorithms work. Topics include particle swarm optimization, ant and bee algorithms, simulated annealing, cuckoo search, firefly algorithm, bat algorithm, flower algorithm, harmony search, algorithm analysis, constraint handling, hybrid methods, parameter tuning

  14. Gene clusters for insecticidal loline alkaloids in the grass-endophytic fungus Neotyphodium uncinatum.

    Science.gov (United States)

    Spiering, Martin J; Moon, Christina D; Wilkinson, Heather H; Schardl, Christopher L

    2005-03-01

    Loline alkaloids are produced by mutualistic fungi symbiotic with grasses, and they protect the host plants from insects. Here we identify in the fungal symbiont, Neotyphodium uncinatum, two homologous gene clusters (LOL-1 and LOL-2) associated with loline-alkaloid production. Nine genes were identified in a 25-kb region of LOL-1 and designated (in order) lolF-1, lolC-1, lolD-1, lolO-1, lolA-1, lolU-1, lolP-1, lolT-1, and lolE-1. LOL-2 contained the homologs lolC-2 through lolE-2 in the same order and orientation. Also identified was lolF-2, but its possible linkage with either cluster was undetermined. Most lol genes were regulated in N. uncinatum and N. coenophialum, and all were expressed concomitantly with loline-alkaloid biosynthesis. A lolC-2 RNA-interference (RNAi) construct was introduced into N. uncinatum, and in two independent transformants, RNAi significantly decreased lolC expression (P lol-gene products indicate that the pathway has evolved from various different primary and secondary biosynthesis pathways.

  15. Pharmacological Evaluation of Total Alkaloids from Nux Vomica: Effect of Reducing Strychnine Contents

    Directory of Open Access Journals (Sweden)

    Jun Chen

    2014-04-01

    Full Text Available The aim of the study was to investigate the possibility of improving the therapeutic efficacy of the total alkaloid fraction (TAF extracted from processed nux vomica by reducing the strychnine contents. Most strychnine was removed from TAF to obtain the modified total alkaloid fraction (MTAF. The toxicity and pharmacokinetics of TAF and MTAF were further investigated and compared besides their antitumor, analgesic and anti-inflammatory activities. The results showed that the ratios of brucine to strychnine were 1:2.05 and 2.2:1 for TAF and MTAF, respectively, and the toxicity of TAF was about 3.17-fold higher than that of MTAF. Compared to brucine alone, the elimination of brucine was found to be inhibited by other alkaloids in TAF or MTAF except strychnine. Significantly increased pharmacological activities when administered by the oral route were obtained with MTAF in comparison to TAF and nux vomica powder (NVP. In summary, MTAF might replace NVP and TAF in the clinical application of Chinese medicine to obtain much higher efficacy.

  16. Poisonous plants contaminating edible ones and toxic substances in plant foods. Part 3. Pyrrolizidine alkaloids from Heliotropium digynum Forssk. (= H. luteum, Poir.).

    Science.gov (United States)

    Hammouda, F M; Rizk, A M; Ismail, S I; Atteya, S Z; Ghaleb, H A; Madkour, M K; Pohland, A E; Wood, G

    1984-10-01

    Investigation of the alkaloidal constituents of Heliotropium digynum resulted in the isolation of four alkaloids viz. heliotrine, europine, lasiocarpine and 7-angelylheliotrine. Moreover, HPLC and GLC showed the probable presence of heliotridine and some other unidentified minor constituents. A summary of the pharmacotoxicity and biological activity of the ethanolic extract, total alkaloids with special reference to heliotrine is presented.

  17. THE SULFONATION STUDY OF REACTION MECHANISM ON PAPAVERINE ALKALOID BY GC-MS AND FT-IR

    Directory of Open Access Journals (Sweden)

    I Made Sudarma

    2010-06-01

    Full Text Available The aim of this research was to prove theoretical mechanism reaction on the sulfonation of papaverine alkaloid and the result could be used as a reference on the transformation of these alkaloid to the other derivatives. Theoriticaly sulfonation of papaverine (1 by HO-SO2Cl could produced papaverine sulfonyl chloride (1a. The formation of this product was analyzed by analytical thin layer chromatography GC-MS, and FT-IR. These analysis showed the formation of product (1a more favorable than the other. Tlc showed product (1a less polar than papaverine, and supported by GC-MS and infrared which showed molecular ion at m/z 412 due to the presence of -SO2Cl and vibration at 1153,4 dan 1265,2 Cm-1 due to absorption of sulfonyl group.   Keywords: reaction mechanism, sulfonation, papaverine alkaloid.

  18. Geo-inspired model: Agents vectors naturals inspired by the environmental management (AVNG of water tributaries

    Directory of Open Access Journals (Sweden)

    Edwin Eduardo Millán Rojas

    2018-02-01

    Full Text Available Context: Management to care for the environment and the Earth (geo can be source of inspiration for developing models that allow addressing complexity issues; the objective of this research was to develop an additional aspect of the inspired models. The geoinspired model has two features, the first covering aspects related to environmental management and the behavior of natural resources, and the second has a component of spatial location associated with existing objects on the Earth's surface. Method: The approach developed in the research is descriptive and its main objective is the representation or characterization of a case study within a particular context. Results: The result was the design of a model to emulate the natural behavior of the water tributaries of the Amazon foothills, in order to extend the application of the inspired models and allow the use of elements such as geo-referencing and environmental management. The proposed geoinspired model is called “natural vectors agents inspired in environmental management”. Conclusions: The agents vectors naturals inspired by the environmental are polyform elements that can assume the behavior of environmental entities, which makes it possible to achieve progress in other fields of environmental management (use of soil, climate, flora, fauna, and link environmental issues with the structure of the proposed model.

  19. Radioactive labelling of alkaloids with morphine skeleton

    International Nuclear Information System (INIS)

    Toth, Geza; Sirokman, Ferenc

    1985-01-01

    Results achieved by the sup(14)C, sup(125)I and sup(3)H labelling of alkaloids with morphine skeleton for kinetic, receptor, metabolims and pharmacological investigations are summarized and evaluated. The methods for the preparation of sup(3)H labelled dihydromorphine, dihydroethylmorphine, dihydrocodeine, naloxone and naloxazone are described. The compounds have higher specific molar activity than those referred to in literature which makes them suitable for a number of investigations. (author)

  20. Pyrrolizidine alkaloids and diterpenes from Villasenoria orcuttii

    Energy Technology Data Exchange (ETDEWEB)

    Arciniegas, Amira; Perez-Castorena, Ana L.; Gonzalez, Karina; Vivar, Alfonso Romo de, E-mail: alperezc@unam.mx [Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Circuito Exterior, Ciudad Universitaria, Coyoacan, DF (Mexico); Reyes-Lezama, Marisol [Centro Conjunto de Investigacion en Quimica Sustentable, Universidad Autonoma del Estado de Mexico-Universidad Nacional Autonoma de Mexico (UAEM-UNAM), Carretera Toluca-Atlacomulco, Estado de Mexico (Mexico); Villasenor, Jose Luis [Instituto de Biologia, Universidad Nacional Autonoma de Mexico, Circuito Exterior, Ciudad Universitaria, Coyoacan, DF, (Mexico)

    2013-07-15

    The chemical study of Villasenoria orcuttii, the only species of the genus Villasenoria, afforded three acyclic diterpenes, two of them described for the first time. Two pyrrolizidine alkaloids, florosenine and floridanine, among other known compounds were also isolated. The absolute configuration of floridanine was determined by X-ray analysis using anomalous dispersion with Cu K{sub {alpha}} radiation, and its {sup 1}H and {sup 13}C nuclear magnetic resonance (NMR) data were corrected. (author)

  1. Pyrrolizidine alkaloids and diterpenes from Villasenoria orcuttii

    International Nuclear Information System (INIS)

    Arciniegas, Amira; Pérez-Castorena, Ana L.; González, Karina; Vivar, Alfonso Romo de; Reyes-Lezama, Marisol; Villaseñor, José Luis

    2013-01-01

    The chemical study of Villasenoria orcuttii, the only species of the genus Villasenoria, afforded three acyclic diterpenes, two of them described for the first time. Two pyrrolizidine alkaloids, florosenine and floridanine, among other known compounds were also isolated. The absolute configuration of floridanine was determined by X-ray analysis using anomalous dispersion with Cu K α radiation, and its 1 H and 13 C nuclear magnetic resonance (NMR) data were corrected. (author)

  2. Synthetic studies of the zoanthamine alkaloids: the total syntheses of norzoanthamine and zoanthamine.

    Science.gov (United States)

    Yoshimura, Fumihiko; Sasaki, Minoru; Hattori, Izumi; Komatsu, Kei; Sakai, Mio; Tanino, Keiji; Miyashita, Masaaki

    2009-07-06

    The zoanthamine alkaloids, a type of heptacyclic marine alkaloid isolated from colonial zoanthids of the genus Zoanthus sp., have distinctive biological and pharmacological properties in addition to their unique chemical structures with stereochemical complexity. Namely, norzoanthamine (1) can suppress the loss of bone weight and strength in ovariectomized mice and has been expected as a promising candidate for a new type of antiosteoporotic drug, while zoanthamine (2) has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects. Recently, norzoanthamine derivatives were demonstrated to inhibit strongly the growth of P-388 murine leukemia cell lines, in addition to their potent antiplatelet activities on human platelet aggregation. Their distinctive biological properties, combined with novel chemical structures, make this family of alkaloids extremely attractive targets for chemical synthesis. However, the chemical synthesis of the zoanthamine alkaloids has been impeded owing to their densely functionalized complex stereostructures. In this paper, we report the first and highly efficient total syntheses of norzoanthamine (1) and zoanthamine (2) in full detail, which involve stereoselective synthesis of the requisite triene (18) for an intramolecular Diels-Alder reaction via the sequential three-component coupling reactions, the key intramolecular Diels-Alder reaction, and subsequent crucial bis-aminoacetalization as the key steps. Ultimately, we achieved the total synthesis of norzoanthamine (1) in 41 steps with an overall yield of 3.5 % (an average of 92 % yield each step) and that of zoanthamine (2) in 43 steps with an overall yield of 2.2 % (an average of 91 % yield each step) starting from (R)-5-methylcyclohexenone (3), respectively.

  3. Therapeutic effects of Sophora moorcroftiana alkaloids in combination with albendazole in mice experimentally infected with protoscolices of Echinococcus granulosus

    Directory of Open Access Journals (Sweden)

    X.M. Ma

    2007-10-01

    Full Text Available The objective of the present study was to determine if the combination of alkaloids from Sophora moorcroftiana seeds and albendazole might be effective in the treatment of experimental echinococcosisin female NIH mice (6 weeks old and weighing 18-20 g, N = 8 in each group infected withprotoscolices of Echinococcus granulosus. Viable protoscolices (N = 6 x 103 were cultured in vitro in 1640 medium and mortality was calculated daily. To determine the in vivo efficacy, mice were inoculated intraperitoneally with viable protoscolices and then treated once daily by gavage for three months with the alkaloids (50 mg kg-1 day-1 and albendazole (50 mg kg-1 day-1, separately and in combination (both alkaloids at 25 mg kg-1 day-1 and albendazole at 25 mg kg-1 day-1. Next, the hydatid cysts collected from the peritoneal cavity of the animals were weighed and serum IL-4, IL-2, and IgE levels were analyzed. Administration of alkaloids to cultured protoscolices showed significant dose- and time-dependent killing effects. The weight of hydatid cysts was significantly decreased upon treatment with each drug (P < 0.01, but the decrease was more prominent and the rate of hydatid cyst growth inhibition was much higher (76.1% in the group receiving the combined treatments (18.3 ± 4.6 mg. IL-4 and total IgE were decreased (939 ± 447 pg/mL and 2.03 ± 0.42 IU/mL, respectively in serum from mice treated with alkaloids and albendazole compared with the untreated control (1481 ± 619 pg/mL and 3.31 ± 0.37 IU/mL; P < 0.01. These results indicate that S. moorcroftiana alkaloids have protoscolicidal effects and the combination of alkaloids and albendazole has significant additive effects.

  4. Skeletal muscle atrophy in bioengineered skeletal muscle: a new model system.

    Science.gov (United States)

    Lee, Peter H U; Vandenburgh, Herman H

    2013-10-01

    Skeletal muscle atrophy has been well characterized in various animal models, and while certain pathways that lead to disuse atrophy and its associated functional deficits have been well studied, available drugs to counteract these deficiencies are limited. An ex vivo tissue-engineered skeletal muscle offers a unique opportunity to study skeletal muscle physiology in a controlled in vitro setting. Primary mouse myoblasts isolated from adult muscle were tissue engineered into bioartificial muscles (BAMs) containing hundreds of aligned postmitotic muscle fibers expressing sarcomeric proteins. When electrically stimulated, BAMs generated measureable active forces within 2-3 days of formation. The maximum isometric tetanic force (Po) increased for ∼3 weeks to 2587±502 μN/BAM and was maintained at this level for greater than 80 days. When BAMs were reduced in length by 25% to 50%, muscle atrophy occurred in as little as 6 days. Length reduction resulted in significant decreases in Po (50.4%), mean myofiber cross-sectional area (21.7%), total protein synthesis rate (22.0%), and noncollagenous protein content (6.9%). No significant changes occurred in either the total metabolic activity or protein degradation rates. This study is the first in vitro demonstration that length reduction alone can induce skeletal muscle atrophy, and establishes a novel in vitro model for the study of skeletal muscle atrophy.

  5. A Tale of Three Cell Types: Alkaloid Biosynthesis Is Localized to Sieve Elements in Opium Poppy

    Science.gov (United States)

    Bird, David A.; Franceschi, Vincent R.; Facchini, Peter J.

    2003-01-01

    Opium poppy produces a diverse array of pharmaceutical alkaloids, including the narcotic analgesics morphine and codeine. The benzylisoquinoline alkaloids of opium poppy accumulate in the cytoplasm, or latex, of specialized laticifers that accompany vascular tissues throughout the plant. However, immunofluorescence labeling using affinity-purified antibodies showed that three key enzymes, (S)-N-methylcoclaurine 3′-hydroxylase (CYP80B1), berberine bridge enzyme (BBE), and codeinone reductase (COR), involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine, are restricted to the parietal region of sieve elements adjacent or proximal to laticifers. The localization of laticifers was demonstrated using antibodies specific to the major latex protein (MLP), which is characteristic of the cell type. In situ hybridization showed that CYP80B1, BBE, and COR gene transcripts were found in the companion cell paired with each sieve element, whereas MLP transcripts were restricted to laticifers. The biosynthesis and accumulation of alkaloids in opium poppy involves cell types not implicated previously in plant secondary metabolism and dramatically extends the function of sieve elements beyond the transport of solutes and information macromolecules in plants. PMID:14508000

  6. BALANOL ANALOGUES

    DEFF Research Database (Denmark)

    1997-01-01

    The present invention relates to a solid phase methodology for the preparation of a combinatorial library of structural analogues of the natural product balanol (ophiocordin, azepinostatin), which is a protein kinase C (PKC) and protein kinase A (PKA) inhibitor. The method comprises solid...

  7. Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis

    Science.gov (United States)

    Crotalaria genus belongs to the subfamily Papilionoideae comprising about 600 species spread throughout tropical, neotropical and subtropical regions. In this study, seeds of Crolatalaria pallida were used to the isolation of usaramine, a pyrrolizidine alkaloid. Thus, Pseudomonas aeruginosa and Stap...

  8. The role of biocatalysis in the asymmetric synthesis of alkaloids

    NARCIS (Netherlands)

    Schrittwieser, J.H.; Resch, V.

    2013-01-01

    Alkaloids are not only one of the most intensively studied classes of natural products, their wide spectrum of pharmacological activities also makes them indispensable drug ingredients in both traditional and modern medicine. Among the methods for their production, biotechnological approaches are

  9. The ergot alkaloid gene cluster: Functional analyses and evolutionary aspects

    Czech Academy of Sciences Publication Activity Database

    Lorenz, N.; Haarmann, T.; Pažoutová, Sylvie; Jung, M.; Tudzynski, P.

    2009-01-01

    Roč. 70, 15-16 (2009), s. 1822-1832 ISSN 0031-9422 Institutional research plan: CEZ:AV0Z50200510 Keywords : Claviceps purpurea * Ergot fungus * Ergot alkaloid gene cluster Subject RIV: EE - Microbiology, Virology Impact factor: 3.104, year: 2009

  10. An atlas of normal skeletal scintigraphy

    International Nuclear Information System (INIS)

    Flanagan, J.J.; Maisey, M.N.

    1985-01-01

    This atlas was compiled to provide the neophyte as well as the experienced radiologist and the nuclear medicine physician with a reference on normal skeletal scintigraphy as an aid in distinguishing normal variations in skeletal uptake from abnormal findings. Each skeletal scintigraph is labeled, and utilizing an identical scale, a relevant skeletal photograph and radiograph are placed adjacent to the scintigraph

  11. The exercised skeletal muscle: a review

    Directory of Open Access Journals (Sweden)

    Marina Marini

    2010-09-01

    Full Text Available The skeletal muscle is the second more plastic tissue of the body - second to the nervous tissue only. In fact, both physical activity and inactivity contribute to modify the skeletal muscle, by continuous signaling through nerve impulses, mechanical stimuli and humoral clues. In turn, the skeletal muscle sends signals to the body, thus contributing to its homeostasis. We'll review here the contribute of physical exercise to the shaping of skeletal muscle, to the adaptation of its mass and function to the different needs imposed by different physical activities and to the attainment of the health benefits associated with active skeletal muscles. Focus will primarily be on the molecular pathways and on gene regulation that result in skeletal muscle adaptation to exercise.

  12. Norsk inspiration til uddannelse og job

    DEFF Research Database (Denmark)

    Skovhus, Randi Boelskifte; Thomsen, Rie; Buhl, Rita

    2017-01-01

    Anmeldelse af bog om det norske fag Utdanningsvalg - inspiration til arbejde med uddannelse og job......Anmeldelse af bog om det norske fag Utdanningsvalg - inspiration til arbejde med uddannelse og job...

  13. Feeling Is Believing: Inspiration Encourages Belief in God.

    Science.gov (United States)

    Critcher, Clayton R; Lee, Chan Jean

    2018-05-01

    Even without direct evidence of God's existence, about half of the world's population believes in God. Although previous research has found that people arrive at such beliefs intuitively instead of analytically, relatively little research has aimed to understand what experiences encourage or legitimate theistic belief systems. Using cross-cultural correlational and experimental methods, we investigated whether the experience of inspiration encourages a belief in God. Participants who dispositionally experience more inspiration, were randomly assigned to relive or have an inspirational experience, or reported such experiences to be more inspirational all showed stronger belief in God. These effects were specific to inspiration (instead of adjacent affective experiences) and a belief in God (instead of other empirically unverifiable claims). Being inspired by someone or something (but not inspired to do something) offers a spiritually transcendent experience that elevates belief in God, in part because it makes people feel connected to something beyond themselves.

  14. [Evaluation of crude drugs by means of colorimeter (I). Study on correlation between color and alkaloids content of coptidis rhizoma].

    Science.gov (United States)

    Yoshimitsu, Michiyo; Qu, Xian-You; Luo, Wei-Zao; Qin, Song-Yun

    2014-05-01

    To examine the correlation between alkaloids content and L*, a* and b* color indices of Rhizoma Coptidis for quality control. A colorimeter was used for the measurement of reflected light from sieved powder samples using the CIE 1976 L* a* b* color system. The content of six alkaloids were determined by HPLC. The correlation between alkaloids content and color indices of Rhizoma Coptidis was analyzed. When the particle size of Rhizoma Coptidis was less than 355 microm and the colorimeter parameters were set as measurement diameter of 3 mm, observation degree of 10, and light source of F2 and F7, the measured color was significantly correlated with total alkaloids content (r = 0.793, P < 0.05). As light source of F11, the measured color was significantly correlated with berberine content (r = 0.867, P < 0.01). The correlation between the color of powdered Coptidis Rhizoma and its alkaloids contents was found in this study. Measurment of the color of Coptidis Rhizoma can be used to assess its quality.

  15. Pyrrolizidine alkaloids in the food chain: development, validation, and application of a new HPLC-ESI-MS/MS sum parameter method.

    Science.gov (United States)

    Cramer, Luise; Schiebel, Hans-Martin; Ernst, Ludger; Beuerle, Till

    2013-11-27

    Contamination of food and feed with pyrrolizidine alkaloids is currently discussed as a potential health risk. Here, we report the development of a new HPLC-ESI-MS/MS sum parameter method to quantitate the pyrrolizidine alkaloid content in complex food matrices. The procedure was validated for honey and culinary herbs. Isotopically labeled 7-O-9-O-dibutyroyl-[9,9-(2)H2]-retronecine was synthesized and utilized as an internal standard for validation and quantitation. The total pyrrolizidine alkaloid content of a sample is expressed as a single sum parameter: retronecine equivalents (RE). Ld/Lq for honey was 0.1 μg RE/kg/0.3 μg RE/kg. For culinary herbs, 1.0 μg RE/kg/3.0 μg RE/kg (dry weight, dw) and 0.1 μg RE/kg/0.3 μg RE/kg (fresh weight, fw) were determined, respectively. The new method was applied to analyze 21 herbal convenience products. Fifteen products (71%) were pyrrolizidine alkaloid positive showing pyrrolizidine alkaloid concentrations ranging from 0.9 to 74 μg RE/kg fw.

  16. in Skeletal Muscle

    Directory of Open Access Journals (Sweden)

    Espen E. Spangenburg

    2011-01-01

    Full Text Available Triglyceride storage is altered across various chronic health conditions necessitating various techniques to visualize and quantify lipid droplets (LDs. Here, we describe the utilization of the BODIPY (493/503 dye in skeletal muscle as a means to analyze LDs. We found that the dye was a convenient and simple approach to visualize LDs in both sectioned skeletal muscle and cultured adult single fibers. Furthermore, the dye was effective in both fixed and nonfixed cells, and the staining seemed unaffected by permeabilization. We believe that the use of the BODIPY (493/503 dye is an acceptable alternative and, under certain conditions, a simpler method for visualizing LDs stored within skeletal muscle.

  17. Gene Clusters for Insecticidal Loline Alkaloids in the Grass-Endophytic Fungus Neotyphodium uncinatum

    OpenAIRE

    Spiering, Martin J.; Moon, Christina D.; Wilkinson, Heather H.; Schardl, Christopher L.

    2005-01-01

    Loline alkaloids are produced by mutualistic fungi symbiotic with grasses, and they protect the host plants from insects. Here we identify in the fungal symbiont, Neotyphodium uncinatum, two homologous gene clusters (LOL-1 and LOL-2) associated with loline-alkaloid production. Nine genes were identified in a 25-kb region of LOL-1 and designated (in order) lolF-1, lolC-1, lolD-1, lolO-1, lolA-1, lolU-1, lolP-1, lolT-1, and lolE-1. LOL-2 contained the homologs lolC-2 through lolE-2 in the same ...

  18. A review on indole alkaloids isolated from Uncaria rhynchophylla and their pharmacological studies.

    Science.gov (United States)

    Ndagijimana, Andre; Wang, Xiaoming; Pan, Guixiang; Zhang, Fan; Feng, Hong; Olaleye, Olajide

    2013-04-01

    Uncaria rhynchophylla (Miq.) Jacks, Rubiaceae, is one of the original plants of the important Chinese crude drug, Gou-teng, mainly used for the treatment of convulsion, hypertension, epilepsy, eclampsia, and cerebral diseases. The pharmacological activities of this plant are related to the presence of active compounds predominantly indole alkaloids. In this article, we have reviewed some reports about the pharmacological activities of the main indole alkaloids isolated from U. rhynchophylla. This review paper will contribute to the studies on the chemistry, safety and quality control of medicinal preparations containing Uncaria species. Copyright © 2013 Elsevier B.V. All rights reserved.

  19. [Analysis of dynamic changes of flavonoids and alkaloids during different drying process of Morus alba leaves].

    Science.gov (United States)

    Bai, Yong-liang; Duan, Jin-ao; Su, Shu-lan; Qian, Ye-fei; Qian, Da-wei; Ouyang, Zhen

    2014-07-01

    To find out dynamic changes of flavonoids and alkaloids in Morus alba leaves by analyzing influence of different drying method and drying degrees, in order to provide evidence for quality evaluation of Morus alba leaves. Different drying methods, programmed temperature methods and constant temperature methods were adopted to dry Morus alba leaves samples respectively. Contents of flavonoids and alkaloids were analyzed by HPLC-PDA and LC-TQ/MS respectively. It's shown obviously that the content of flavonoids were influenced heavily by different drying methods. Methods that suitable for flavonoids were freezing-dried > shade-dried > dried > sun-dried > microwave-dried > infrared-dried; Methods that suitable for alkaloids were freezing-dried > shade-dried > dried > sun-dried > infrared-dried > microwave-dried. The 55 -65 degrees C group was shown to be the lowest in both flavonoids and DNJ while the 85 - 95 degrees C group was shown to be the best for DNJ. For fagomine, the 45 degrees C group was shown to be the lowest concentrations while the 95 - 105 degrees C group was shown to be the highest. Samples with different moisture were shown to be different in content of flavonoids and alkaloids. And samples with 10% moisture contain highest flavonoids while those with 30% - 50% moisture contain lowest flavonoids. Content of DNJ and fagomine raised as moisture decreasing. In addition, the 55 - 65 degrees C group was better than the 95 -105 degrees C one in alkaloids content. The results provide optimal drying methods and condition for drying Morus alba leaves, and foundations for uncovering biochemical transform of Morus alba leaves.

  20. Cephalostatin analogues--synthesis and biological activity.

    Science.gov (United States)

    Flessner, Timo; Jautelat, Rolf; Scholz, Ulrich; Winterfeldt, Ekkehard

    2004-01-01

    Starting off in the early 90's the field of cephalostatin analogues has continually expanded over the last 10 years. First syntheses prepared symmetric analogues like 14b (119) and 26 (65), which were subsequently desymmetrized to provide analogues like beta-hydroxy ketone 31 (19). Importantly the straightforward approach provided already compounds with mu-molar potency and the same pattern of activity as cephalostatin 1 (1) (see Chapter 2.1). Chemically more demanding, two new methods for the directed synthesis of (bissteroidal) pyrazines were devised and subsequently applied to a wide variety of differently functionalized coupling partners. These new methods allowed for the synthesis of various analogues (Chapter 2.2.; and, last but not least, for the totals synthesis of several cephalostatin natural products; Chapter 1.). Functionalization and derivatization of the 12-position was performed (Chapter 2.1 and 3) and synthetic approaches to establish the D-ring double bond were successfully investigated (Chapter 3). [figure: see text] Dealing synthetically with the spiroketal moiety, novel oxidative opening procedures on monomeric delta 14, 15-steroids were devised as well as intensive studies regarding spiroketal synthesis and spiroketal rearrangements were conducted (Chapter 3.2. and 4.). Last but not least direct chemical modification of ritterazines and cephalostatins were studied, which provided a limited number of ritterazine analogues (Chapter 4.). All these synthetic activities towards analogues are summarized in Fig. 18. During this period of time the growing number of cephalostatins and ritterazines on the one hand and of analogues on the other hand provided several SAR trends, which can guide future analogue synthesis. The combined SAR findings are displayed in Fig. 19. So far it is apparent that: Additional methoxylations or hydroxylations in the steroidal A ring core structure (1-position) are slightly decreasing activity (compare cephalostatin 1 1 to

  1. Antiplasmodial Activity, Cytotoxicity and Structure-Activity Relationship Study of Cyclopeptide Alkaloids

    Directory of Open Access Journals (Sweden)

    Emmy Tuenter

    2017-02-01

    Full Text Available Cyclopeptide alkaloids are polyamidic, macrocyclic compounds, containing a 13-, 14-, or 15-membered ring. The ring system consists of a hydroxystyrylamine moiety, an amino acid, and a β-hydroxy amino acid; attached to the ring is a side chain, comprised of one or two more amino acid moieties. In vitro antiplasmodial activity was shown before for several compounds belonging to this class, and in this paper the antiplasmodial and cytotoxic activities of ten more cyclopeptide alkaloids are reported. Combining these results and the IC50 values that were reported by our group previously, a library consisting of 19 cyclopeptide alkaloids was created. A qualitative SAR (structure-activity relationship study indicated that a 13-membered macrocyclic ring is preferable over a 14-membered one. Furthermore, the presence of a β-hydroxy proline moiety could correlate with higher antiplasmodial activity, and methoxylation (or, to a lesser extent, hydroxylation of the styrylamine moiety could be important for displaying antiplasmodial activity. In addition, QSAR (quantitative structure-activity relationship models were developed, using PLS (partial least squares regression and MLR (multiple linear regression. On the one hand, these models allow for the indication of the most important descriptors (molecular properties responsible for the antiplasmodial activity. Additionally, predictions made for interesting structures did not contradict the expectations raised in the qualitative SAR study.

  2. Analogue to Digital and Digital to Analogue (AD/DA) Conversion Techniques: An Overview

    CERN Multimedia

    CERN. Geneva

    2002-01-01

    The basic ideas behind modern Analogue to Digital and Digital to Analogue (AD/DA) conversion methods will be introduced: a general view of the importance of these devices will be given, along with the digital representation of time-varying, real-world analogue signals. Some CERN applications will be outlined. The variety of conversion methods, their limitations, error sources and measurement methods will form the major part of this presentation. A review of the technological progress in this field over the last 30 years will be presented, concluding with the present 'state of the art' and a quick look at what is just around the corner. This Technical Training Seminar is in the framework of the FEED-2002 Lecture Series, and it is a prerequisite to attending to any of the FEED-2002 Terms. FEED-2002 is a two-term course that will review the techniques dealing with closed loop systems, focussing on time-invariant linear systems. (free attendance, no registration required) More information on the FEED-2002 ...

  3. The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus).

    Science.gov (United States)

    Brown, Ammon W; Stegelmeier, Bryan L; Colegate, Steven M; Gardner, Dale R; Panter, Kip E; Knoppel, Edward L; Hall, Jeffery O

    2016-05-01

    Comfrey (Symphytum officinale), a commonly used herb, contains dehydropyrrolizidine alkaloids that, as a group of bioactive metabolites, are potentially hepatotoxic, pneumotoxic, genotoxic and carcinogenic. Consequently, regulatory agencies and international health organizations have recommended comfrey be used for external use only. However, in many locations comfrey continues to be ingested as a tisane or as a leafy vegetable. The objective of this work was to compare the toxicity of a crude, reduced comfrey alkaloid extract to purified lycopsamine and intermedine that are major constituents of S. officinale. Male, California White chicks were orally exposed to daily doses of 0.04, 0.13, 0.26, 0.52 and 1.04 mmol lycopsamine, intermedine or reduced comfrey extract per kg bodyweight (BW) for 10 days. After another 7 days chicks were euthanized. Based on clinical signs of poisoning, serum biochemistry, and histopathological analysis the reduced comfrey extract was more toxic than lycopsamine and intermedine. This work suggests a greater than additive effect of the individual alkaloids and/or a more potent toxicity of the acetylated derivatives in the reduced comfrey extract. It also suggests that safety recommendations based on purified compounds may underestimate the potential toxicity of comfrey. Published 2015. This article has been contributed to by US Government employees and their work is in the public domain in the USA.

  4. Reviewing colchicaceae alkaloids – perspectives of evolution on medicinal chemistry

    DEFF Research Database (Denmark)

    Larsson, Sonny; Rønsted, Nina

    2014-01-01

    . In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance in cancer...

  5. Senecio grisebachii Baker: Pyrrolizidine alkaloids and experimental poisoning in calves

    Science.gov (United States)

    The main objectives of this study were to determine the 1,2-dehydropyrrolizidine alkaloid (DHPA) content in Senecio grisebachii Baker (Compositae), to experimentally demonstrate its toxicity in calves and to describe the main clinical and pathological findings of this toxicity. S. grisebachii plants...

  6. Congenital anomalies and normal skeletal variants

    International Nuclear Information System (INIS)

    Guebert, G.M.; Yochum, T.R.; Rowe, L.J.

    1987-01-01

    Congenital anomalies and normal skeletal variants are a common occurrence in clinical practice. In this chapter a large number of skeletal anomalies of the spine and pelvis are reviewed. Some of the more common skeletal anomalies of the extremities are also presented. The second section of this chapter deals with normal skeletal variants. Some of these variants may simulate certain disease processes. In some instances there are no clear-cut distinctions between skeletal variants and anomalies; therefore, there may be some overlap of material. The congenital anomalies are presented initially with accompanying text, photos, and references, beginning with the skull and proceeding caudally through the spine to then include the pelvis and extremities. The normal skeletal variants section is presented in an anatomical atlas format without text or references

  7. Biosynthesis of a new tobacco alkaloid, hydroxy-N-acylnornicotine in the trichomes of Nicotiana stocktonii

    International Nuclear Information System (INIS)

    Zador, E.; Jones, D.

    1986-01-01

    A new tobacco alkaloid from section Repandae is highly toxic to an insect (Manduca sexta) unsusceptible to previously described nicotine alkaloids (1). They have localized the alkaloid, HO-N-acylnornicotine (HO-NAN) nearly entirely to the exudate secreted by the epidermal trichomes of N. stocktonii. Only the nicotine and nornicotine were found in abundance inside the trichomes, while primarily nicotine was present inside the aerial vegetative parts and root. These results suggest that the HO-NAN is synthesized by the trichomes. When unlabelled nicotine was fed to isolated leaves there was an increase in internal nicotine, nornicotine and secretion of HO-NAN. Feeding leaves with 2'-C 14 nicotine resulted in labelling of both nornicotine and HO-NAN. These data strongly suggest synthesis of HO-NAN from nicotine via nornicotine in the trichomes, followed by rapid secretion. The possible evolutionary significance of this pathway of synthesis and secretion is discussed

  8. Homospermidine synthase, the first pathway-specific enzyme of pyrrolizidine alkaloid biosynthesis, evolved from deoxyhypusine synthase

    Science.gov (United States)

    Ober, Dietrich; Hartmann, Thomas

    1999-01-01

    Pyrrolizidine alkaloids are preformed plant defense compounds with sporadic phylogenetic distribution. They are thought to have evolved in response to the selective pressure of herbivory. The first pathway-specific intermediate of these alkaloids is the rare polyamine homospermidine, which is synthesized by homospermidine synthase (HSS). The HSS gene from Senecio vernalis was cloned and shown to be derived from the deoxyhypusine synthase (DHS) gene, which is highly conserved among all eukaryotes and archaebacteria. DHS catalyzes the first step in the activation of translation initiation factor 5A (eIF5A), which is essential for eukaryotic cell proliferation and which acts as a cofactor of the HIV-1 Rev regulatory protein. Sequence comparison provides direct evidence for the evolutionary recruitment of an essential gene of primary metabolism (DHS) for the origin of the committing step (HSS) in the biosynthesis of pyrrolizidine alkaloids. PMID:10611289

  9. Discovery of skin alkaloids in a miniaturized eleutherodactylid frog from Cuba.

    Science.gov (United States)

    Rodríguez, Ariel; Poth, Dennis; Schulz, Stefan; Vences, Miguel

    2011-06-23

    Four phylogenetically independent lineages of frogs are currently known to sequester lipid-soluble skin alkaloids for which a dietary source has been demonstrated. We report here a remarkable fifth such instance, in Eleutherodactylus iberia and Eleutherodactylus orientalis, two species of miniaturized frogs of the family Eleutherodactylidae from Cuba. Six pumiliotoxins and two indolizidines were found in E. iberia, one of the smallest frogs in the world and characterized by a contrasting colour pattern for which we hypothesize an aposematic function. Analyses of stomach content indicated a numerical prevalence of mites with an important proportion of oribatids-a group of arthropods known to contain one of the pumiliotoxins detected in E. iberia. This suggests that miniaturization and specialization to small prey may have favoured the acquisition of dietary skin alkaloids in these amphibians.

  10. Pyrrolizidine Alkaloids from Echium vulgare in Honey Originate Primarily from Floral Nectar.

    Science.gov (United States)

    Lucchetti, Matteo A; Glauser, Gaetan; Kilchenmann, Verena; Dübecke, Arne; Beckh, Gudrun; Praz, Christophe; Kast, Christina

    2016-06-29

    Pyrrolizidine alkaloids (PAs) in honey can be a potential human health risk. So far, it has remained unclear whether PAs in honey originate from pollen or floral nectar. We obtained honey, nectar, and plant pollen from two observation sites where Echium vulgare L. was naturally abundant. The PA concentration of honey was determined by targeted analysis using a high pressure liquid chromatography-mass spectrometry system (HPLC-MS/MS), allowing the quantification of six different PAs and PA-N-oxides present in E. vulgare. Echium-type PAs were detected up to 0.153 μg/g in honey. Nectar and plant pollen were analyzed by nontargeted analysis using ultrahigh pressure liquid chromatography-high resolution-mass spectrometry (UHPLC-HR-MS), allowing the detection of 10 alkaloids in small size samples. Echium-type PAs were detected between 0.3-95.1 μg/g in nectar and 500-35000 μg/g in plant pollen. The PA composition in nectar and plant pollen was compared to the composition in honey. Echimidine (+N-oxide) was the main alkaloid detected in honey and nectar samples, while echivulgarine (+N-oxide) was the main PA found in plant pollen. These results suggest that nectar contributes more significantly to PA contamination in honey than plant pollen.

  11. Paradigms for biologically inspired design

    DEFF Research Database (Denmark)

    Lenau, T. A.; Metzea, A.-L.; Hesselberg, T.

    2018-01-01

    engineering, medical engineering, nanotechnology, photonics,environmental protection and agriculture. However, a major obstacle for the wider use of biologically inspired design isthe knowledge barrier that exist between the application engineers that have insight into how to design suitable productsand......Biologically inspired design is attracting increasing interest since it offers access to a huge biological repository of wellproven design principles that can be used for developing new and innovative products. Biological phenomena can inspireproduct innovation in as diverse areas as mechanical...... the biologists with detailed knowledge and experience in understanding how biological organisms function in theirenvironment. The biologically inspired design process can therefore be approached using different design paradigmsdepending on the dominant opportunities, challenges and knowledge characteristics...

  12. Double stranded viral RNA induces inflammation and insulin resistance in skeletal muscle from pregnant women in vitro.

    Science.gov (United States)

    Lappas, Martha

    2015-05-01

    Maternal peripheral insulin resistance and increased inflammation are two features of pregnancies complicated by pre-existing maternal obesity and gestational diabetes mellitus (GDM). There is now increasing evidence that activation of Toll-like receptor (TLR) signalling pathways by viral products may play a role in the pathophysiology of diabetes. Thus, the aim of this study was to assess the effect of the TLR3 ligand and viral dsRNA analogue polyinosinic polycytidilic acid (poly(I:C)) on inflammation and the insulin signalling pathway in skeletal muscle from pregnant women. Human skeletal muscle tissue explants were performed to determine the effect of poly(I:C) on the expression and secretion of markers of inflammation, and the insulin signalling pathway and glucose uptake. Poly(I:C) significantly increased the expression of a number of inflammatory markers in skeletal muscle from pregnant women. Specifically, there was an increase in the expression and/or secretion of the pro-inflammatory cytokines TNF-α, and IL-6 and the pro-inflammatory chemokines IL-8 and MCP-1. These effect of poly(I:C) appear to mediated via a number of signalling molecules including the pro-inflammatory transcription factor NF-κB, and the serine threonine kinases GSK3 and AMPKα. Additionally, poly(I:C) decreased insulin stimulated GLUT-4 expression and glucose uptake in skeletal muscle from pregnant women. The in vitro data presented in this study suggests that viral infection may contribute to the pathophysiology of pregnancies complicated by pre-existing maternal obesity and/or GDM. It should be noted that the in vitro studies cannot be directly used to infer the same outcomes in the intact subject. Copyright © 2015 Elsevier Inc. All rights reserved.

  13. International video project on natural analogues

    International Nuclear Information System (INIS)

    Guentensperger, Marcel

    1993-01-01

    A natural analogue can be defined as a natural process which has occurred in the past and is studied in order to test predictions about the future evolution of similar processes. In recent years, natural analogues have been used increasingly to test the mathematical models required for repository performance assessment. Analogues are, however, also of considerable use in public relations as they allow many of the principles involved in demonstrating repository safety to be illustrated in a clear manner using natural systems with which man is familiar. The international Natural Analogue Working Group (NAWG), organised under the auspices of the CEC, has recognised that such PR applications are of considerable importance and should be supported from a technical level. At the NAWG meeting in Pitlochry, Scotland (June 1990), it was recommended that the possibilities for making a video film on this topic be investigated and Nagra was requested to take the lead role in setting up such a project

  14. Skeletal Stability after Large Mandibular Advancement (> 10 mm) with Bilateral Sagittal Split Osteotomy and Skeletal Elastic Intermaxillary Fixation

    DEFF Research Database (Denmark)

    Schwartz, Kristoffer; Rodrigo, Maria; Jensen, Thomas

    2016-01-01

    OBJECTIVES: The aim of the present study was to assess the skeletal stability after large mandibular advancement (> 10 mm) with bilateral sagittal split osteotomy and skeletal elastic intermaxillary fixation and to correlate the skeletal stability with the vertical facial type. MATERIAL AND METHODS......: A total of 33 consecutive patients underwent bimaxillary surgery to correct skeletal Class II malocclusion with a mandibular advancement (> 10 mm) measured at B-point and postoperative skeletal elastic intermaxillary fixation for 16 weeks. Skeletal stability was evaluated using lateral cephalometric...... radiographs obtained preoperative (T1), 8 weeks postoperatively (T2), and 18 month postoperatively (T3). B-point and pogonion (Pog) was used to measure the skeletal relapse and the mandibular plane angle (MP-angle) was used to determine the vertical facial type. RESULTS: The mean advancement from T1 to T2...

  15. Lysergic acid amide as chemical marker for the total ergot alkaloids in rye flour - Determination by high-performance thin-layer chromatography-fluorescence detection.

    Science.gov (United States)

    Oellig, Claudia

    2017-07-21

    Ergot alkaloids are generally determined by high-performance liquid chromatography (HPLC) coupled to fluorescence detection (FLD) or mass selective detection, analyzing the individual compounds. However, fast and easy screening methods for the determination of the total ergot alkaloid content are more suitable, since for monitoring only the sum of the alkaloids is relevant. The herein presented screening uses lysergic acid amide (LSA) as chemical marker, formed from ergopeptine alkaloids, and ergometrine for the determination of the total ergot alkaloids in rye with high-performance thin-layer chromatography-fluorescence detection (HPTLC-FLD). An ammonium acetate buffered extraction step was followed by liquid-liquid partition for clean-up before the ergopeptine alkaloids were selectively transformed to LSA and analyzed by HPTLC-FLD on silica gel with isopropyl acetate/methanol/water/25% ammonium hydroxide solution (80:10:3.8:1.1, v/v/v/v) as the mobile phase. The enhanced native fluorescence of LSA and unaffected ergometrine was used for quantitation without any interfering matrix. Limits of detection and quantitation were 8 and 26μg LSA/kg rye, which enables the determination of the total ergot alkaloids far below the applied quality criterion limit for rye. Close to 100% recoveries for different rye flours at relevant spiking levels were obtained. Thus, reliable results were guaranteed, and the fast and efficient screening for the total ergot alkaloids in rye offers a rapid alternative to the HPLC analysis of the individual compounds. Copyright © 2017 Elsevier B.V. All rights reserved.

  16. Dioxygenases Catalyze O-Demethylation and O,O-Demethylenation with Widespread Roles in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy*

    Science.gov (United States)

    Farrow, Scott C.; Facchini, Peter J.

    2013-01-01

    In opium poppy, the antepenultimate and final steps in morphine biosynthesis are catalyzed by the 2-oxoglutarate/Fe(II)-dependent dioxygenases, thebaine 6-O-demethylase (T6ODM) and codeine O-demethylase (CODM). Further investigation into the biochemical functions of CODM and T6ODM revealed extensive and unexpected roles for such enzymes in the metabolism of protopine, benzo[c]phenanthridine, and rhoeadine alkaloids. When assayed with a wide range of benzylisoquinoline alkaloids, CODM, T6ODM, and the functionally unassigned paralog DIOX2, renamed protopine O-dealkylase, showed novel and efficient dealkylation activities, including regio- and substrate-specific O-demethylation and O,O-demethylenation. Enzymes catalyzing O,O-demethylenation, which cleave a methylenedioxy bridge leaving two hydroxyl groups, have previously not been reported in plants. Similar cleavage of methylenedioxy bridges on substituted amphetamines is catalyzed by heme-dependent cytochromes P450 in mammals. Preferred substrates for O,O-demethylenation by CODM and protopine O-dealkylase were protopine alkaloids that serve as intermediates in the biosynthesis of benzo[c]phenanthridine and rhoeadine derivatives. Virus-induced gene silencing used to suppress the abundance of CODM and/or T6ODM transcripts indicated a direct physiological role for these enzymes in the metabolism of protopine alkaloids, and they revealed their indirect involvement in the formation of the antimicrobial benzo[c]phenanthridine sanguinarine and certain rhoeadine alkaloids in opium poppy. PMID:23928311

  17. Dioxygenases catalyze O-demethylation and O,O-demethylenation with widespread roles in benzylisoquinoline alkaloid metabolism in opium poppy.

    Science.gov (United States)

    Farrow, Scott C; Facchini, Peter J

    2013-10-04

    In opium poppy, the antepenultimate and final steps in morphine biosynthesis are catalyzed by the 2-oxoglutarate/Fe(II)-dependent dioxygenases, thebaine 6-O-demethylase (T6ODM) and codeine O-demethylase (CODM). Further investigation into the biochemical functions of CODM and T6ODM revealed extensive and unexpected roles for such enzymes in the metabolism of protopine, benzo[c]phenanthridine, and rhoeadine alkaloids. When assayed with a wide range of benzylisoquinoline alkaloids, CODM, T6ODM, and the functionally unassigned paralog DIOX2, renamed protopine O-dealkylase, showed novel and efficient dealkylation activities, including regio- and substrate-specific O-demethylation and O,O-demethylenation. Enzymes catalyzing O,O-demethylenation, which cleave a methylenedioxy bridge leaving two hydroxyl groups, have previously not been reported in plants. Similar cleavage of methylenedioxy bridges on substituted amphetamines is catalyzed by heme-dependent cytochromes P450 in mammals. Preferred substrates for O,O-demethylenation by CODM and protopine O-dealkylase were protopine alkaloids that serve as intermediates in the biosynthesis of benzo[c]phenanthridine and rhoeadine derivatives. Virus-induced gene silencing used to suppress the abundance of CODM and/or T6ODM transcripts indicated a direct physiological role for these enzymes in the metabolism of protopine alkaloids, and they revealed their indirect involvement in the formation of the antimicrobial benzo[c]phenanthridine sanguinarine and certain rhoeadine alkaloids in opium poppy.

  18. Indole alkaloids and terpenoids from Tabernaemontana markgrafiana

    DEFF Research Database (Denmark)

    Nielsen, H.B.; Hazell, A.; Hazell, R.

    1994-01-01

    The bark of Tabernaemontana markgrafiana yielded five acetylated pentacyclic triterpenes and 24 monoterpene indole alkaloids. The major triterpene was baurenyl acetate, which constituted ca 6% of the crude petrol extract. An X-ray study of iso-ursenyl acetate was carried out for the first time...

  19. Two new tropolonic alkaloids from Colchicum speciosum Steven bulbs

    Directory of Open Access Journals (Sweden)

    S. Tayyeb*

    2017-11-01

    Full Text Available Background and objectives: The genus Colchicum belongs to the family Colchicaceae, which comprises of 19 genera, and 225 species worldwide. They have been recognized for more than 2000 years for their noticeable biological properties. The Colchicum species are well known for presence of tropolonic alkaloids, mainly colchicine. Colchicine, is still the drug of choice for treatment of gout, and is used for the treatment of a number of proinflammatory disorders, such as familial Mediterranean fever, and Behcet’s disease. Clinical studies have proved colchicine to posses potent anti-tumor activity. Colchicum speciosum Steven is an indigenous perennial herbaceous plant widely distributed in northern, central and western regions of Iran.  Methods: In the present study, the phytochemical composition of MeOH extract from bulbs of C. speciosum collected fromSavadkouh region, Iranwas investigated by combination of HPLC-PDA-MS spectrometry and NMR specroscopy. The fractionation of MeOH extract was carried out by partitioning on CH2Cl2, EtOAc and water. Results: The isolation and purification of CH2Cl2 portion by combination of reverse and normal phase chromatography resulted in the isolation, purification and identification of two new tropolonic alkaloids, compounds (1 and (2, as well as two known compound colchicine (3 and demecolcine (4. Their structures were established by extensive spectroscopic methods, including 1D (1H NMR and 2D-NMR (COSY, HSQC and HMBC. The absolute configurations of isolated compounds were established by aid of circular dichroism. Conclusion: Phytochemical investigation of CH2Cl2 extract of C. speciosum by combination of HPLC, column chromatography and hyphenated spectroscopic techniques led to identification two new alkaloids with potential as lead compounds.

  20. Skeletal manifestations of juvenile hypothyroidism and the impact of treatment on skeletal system.

    Science.gov (United States)

    Gutch, Manish; Philip, Rajeev; Philip, Renjit; Toms, Ajit; Saran, Sanjay; Gupta, K K

    2013-10-01

    Thyroid hormone mediates growth and development of the skeleton through its direct effects and through its permissive effects on growth hormone. The effect of hypothyroidism on bone is well described in congenital hypothyroidism, but the impact of thyroid hormone deficiency on a growing skeleton, as it happens with juvenile hypothyroidism, is less defined. In addition, the extent to which the skeletal defects of juvenile hypothyroidism revert on the replacement of thyroid hormone is not known. A study was undertaken in 29 juvenile autoimmune hypothyroid patients to study the skeletal manifestations of juvenile hypothyroidism and the impact of treatment of hypothyroidism on the skeletal system of juvenile patients. Hypothyroidism has a profound impact on the skeletal system and delayed bone age, dwarfism, and thickened bands at the metaphyseal ends being the most common findings. Post treatment, skeletal findings like delayed bone age and dwarfism improved significantly, but there were no significant changes in enlargement of sella, presence of wormian bones, epihyseal dysgenesis, vertebral changes and thickened band at the metaphyseal ends. With the treatment of hypothyroidism, there is an exuberant advancement of bone age, the catch up of bone age being approximately double of the chronological age advancement.