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Sample records for batzelladine alkaloids synthesis

  1. 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.

  2. Synthesis and biological evaluation of tricyclic guanidine analogues of batzelladine K for antimalarial, antileishmanial, antibacterial, antifungal, and anti-HIV activities.

    Science.gov (United States)

    Ahmed, Nafees; Brahmbhatt, Keyur G; Khan, Shabana I; Jacob, Melissa; Tekwani, Babu L; Sabde, Sudeep; Mitra, Debashis; Singh, Inder P; Khan, Ikhlas A; Bhutani, Kamlesh K

    2013-04-01

    Fifty analogues of batzelladine K were synthesized and evaluated for in vitro antimalarial (Plasmodium falciparum), antileishmanial (Leishmania donovani), antimicrobial (panel of bacteria and fungi), antiviral (HIV-1) activities. Analogues 14h and 20l exhibited potential antimalarial activity against chloroquine-sensitive D6 strain with IC(50) 1.25 and 0.88 μM and chloroquine-resistant W2 strain with IC(50) 1.64 and 1.07 μM, respectively. Analogues 12c and 14c having nonyl substitution showed the most potent antileishmanial activity with IC(50) 2.39 and 2.78 μM and IC(90) 11.27 and 12.76 μM, respectively. Three analogues 12c, 14c, and 14i were the most active against various pathogenic bacteria and fungi with IC(50) Analogue 20l having pentyl and methyl substituents on tricycle showed promising activities against all pathogens. However, none was found active against HIV-1. Our study demonstrated that the tricyclic guanidine compounds provide new structural class for broad spectrum activity. © 2012 John Wiley & Sons A/S.

  3. 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 ...

  4. Two-directional synthesis as a tool for diversity-oriented synthesis: Synthesis of alkaloid scaffolds

    Directory of Open Access Journals (Sweden)

    Kieron M. G. O’Connell

    2012-06-01

    Full Text Available Two-directional synthesis represents an ideal strategy for the rapid elaboration of simple starting materials and their subsequent transformation into complex molecular architectures. As such, it is becoming recognised as an enabling technology for diversity-oriented synthesis. Herein, we provide a thorough account of our work combining two-directional synthesis with diversity-oriented synthesis, with particular reference to the synthesis of polycyclic alkaloid scaffolds.

  5. 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.

  6. Catalytic asymmetric synthesis of the alkaloid (+)-myrtine

    NARCIS (Netherlands)

    Pizzuti, Maria Gabriefla; Minnaard, Adriaan J.; Feringa, Ben L.

    2008-01-01

    A new protocol for the asymmetric synthesis of trans-2,6-disubstituted-4-piperidones has been developed using a catalytic enantioselective conjugate addition reaction in combination with a diastereoselective lithiation-substitution sequence; an efficient synthesis of (+)-myrtine has been achieved

  7. 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...

  8. Approaches to the synthesis of mesembrine and related alkaloids

    International Nuclear Information System (INIS)

    Katz, R.B.

    1983-10-01

    After a survey of the methods reported in the literature for the synthesis of mesembrine and related octahydroindoles, a novel synthetic approach to these alkaloids is presented, based on the use of the vinylogous urethane, 1-methyl-3-(3,4-di-methoxyphenyl)-2-ethoxycarbonylmethylenepyrrolidine, and its immediate precursor, N-methyl-/3-(3,4-dimethoxyphenyl)-2-thiopyrrolidone. Since the most convenient approach to the latter compound is via the corresponding lactam, attempts to prepare this material using N-methyl-2-pyrrolidone, and using methyl 3,4-di-methoxyphenylacetate are presented. Attempts to prepare mesembrine from the 3-aryl vinylogous urethane are then presented, firstly by investigation in a series of model reactions, followed by a sequence designed to lead to mesembrine itself. The failure to prepare mesembrine from the vinylogous urethane leads to the design of a new synthetic route, the crucial step in which is an alkylation on sulphur and sulphide contraction with a halomethyl vinyl ketone, to form a vinylogous amide intermediate. In an appendix the preparation, spectroscopic properties and reactivity towards alkylation of various extended enamines are discussed

  9. 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

  10. 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

  11. 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...

  12. Asymmetric synthesis of synthetic alkaloids by a tandem biocatalysis/Ugi/Pictet-Spengler-type

    NARCIS (Netherlands)

    Znabet, A.; Zonneveld, J.; Janssen, E.; de Kanter, F.J.J.; Helliwell, M.; Turner, N.J.; Ruijter, E.; Orru, R.V.A.

    2010-01-01

    We have combined the biocatalytic desymmetrization of 3,4-cis-substituted meso-pyrrolidines with an Ugi-type multicomponent reaction followed in situ by a Pictet-Spengler-type cyclization reaction sequence for the rapid asymmetric synthesis of alkaloid-like polycyclic compounds. © The Royal Society

  13. New One-Pot Methodologies for the Modification or Synthesis of Alkaloid Scaffolds

    Directory of Open Access Journals (Sweden)

    Amir E. Wahba

    2010-08-01

    Full Text Available There are several avenues by which promising bioactive natural products can be produced in sufficient quantities to enable lead optimization and medicinal chemistry studies. The total synthesis of natural products is an important, but sometimes difficult, approach and requires the development of innovative synthetic methodologies to simplify the synthesis of complex molecules. Various classes of natural product alkaloids are both common and widely distributed in plants, bacteria, fungi, insects and marine organisms. This mini-review will discuss the scope, mechanistic insights and enantioselectivity aspects of selected examples of recently developed one-pot methods that have been published in 2009 for the synthesis of substituted piperidines, quinolizidines, pyrrolidines, hexahydropyrrolizines, octahydroindolizines and g-lactams. In addition, progress on the synthesis of b-carboline (manzamine alkaloids will also be discussed.

  14. 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.

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

    Directory of Open Access Journals (Sweden)

    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.

  16. Synthesis of some 11C-labelled alkaloids

    International Nuclear Information System (INIS)

    Laangstroem, B.; Antoni, G.; Halldin, H.; Svaerd, H.; Bergson, G.

    1982-01-01

    Using ( 11 C)-methyl iodide in N-alkylation reactions in dimethylformamide (DMF), the alkaloids N-( 11 C-methyl)-morphine, N-( 11 C-methyl)-codeine, 6-N(methyl)-9, 10-dihydroergotamine, 6-N-( 11 C-methyl)-bromocriptine and N-( 11 C-methyl)-nicotine have been synthesized in radiochemical yields of 50-95%, within 5-10 min of introducing ( 11 C)-methyl iodide into the reaction vial. ( 11 C)-Methyl iodide was obtained within 4-7 min from ( 11 C)-carbon dioxide prepared by the 14 N(p,α) 11 C reaction. (Authors)

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

    Directory of Open Access Journals (Sweden)

    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.

  18. Studies toward the synthesis of Amaryllidaceae alkaloids from Morita-Baylis-Hillman adducts: a straightforward synthesis of functionalized dihydroisoquinoline-5(6H)-one core

    Energy Technology Data Exchange (ETDEWEB)

    Lopes, Elizandra C.S.; Coelho, Fernando [Universidade Estadual de Campinas, SP (Brazil). Inst. de Quimica]. E-mail: coelho@iqm.unicamp.br

    2007-07-01

    We disclose herein our results concerning a study aiming at the synthesis of the highly substituted carbon skeleton of alkaloids isolated from plants of the Amaryllidaceae family. The total synthesis of the functionalized dihydroisoquinoline-5(6H)-one core, which is the bottom part of the structure of alkaloids isolated from this botanic family, is described, using Morita-Baylis-Hillman adducts as substrate. This compound should be a useful and valuable intermediate for the total synthesis of alkaloids isolated from Amaryllidaceae. (author)

  19. Studies toward the synthesis of Amaryllidaceae alkaloids from Morita-Baylis-Hillman adducts: a straightforward synthesis of functionalized dihydroisoquinoline-5(6H)-one core

    International Nuclear Information System (INIS)

    Lopes, Elizandra C.S.; Coelho, Fernando

    2007-01-01

    We disclose herein our results concerning a study aiming at the synthesis of the highly substituted carbon skeleton of alkaloids isolated from plants of the Amaryllidaceae family. The total synthesis of the functionalized dihydroisoquinoline-5(6H)-one core, which is the bottom part of the structure of alkaloids isolated from this botanic family, is described, using Morita-Baylis-Hillman adducts as substrate. This compound should be a useful and valuable intermediate for the total synthesis of alkaloids isolated from Amaryllidaceae. (author)

  20. A novel toxic alkaloid from poison hemlock (Conium maculatum L., Apiaceae): identification, synthesis and antinociceptive activity.

    Science.gov (United States)

    Radulović, Niko; Dorđević, Nevenka; Denić, Marija; Pinheiro, Mariana Martins Gomes; Fernandes, Patricia Dias; Boylan, Fabio

    2012-02-01

    2-Pentylpiperidine, named conmaculatin, a novel volatile alkaloid related to coniine was identified from the renowned toxic weed Conium maculatum L. (Apiaceae). The structure of conmaculatin was corroborated by synthesis (8 steps starting from cyclohexanol, overall yield 12%). Conmaculatin's strong peripheral and central antinociceptive activity in mice was observed in a narrow dose range (10-20mg/kg). It was found to be lethal in doses higher than 20mg/kg. Copyright © 2011 Elsevier Ltd. All rights reserved.

  1. Synthesis of (R-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids

    Directory of Open Access Journals (Sweden)

    Serkos A Haroutounian

    2007-04-01

    Full Text Available The efficient transformation of D-glucal to (2R-hydroxymethyldihydro-pyridinone 5 in seven steps and 35 % overall yield is reported. Dihydropyridone 5 constitutes a versatile chiral building block for the synthesis of various piperidine alkaloids. In this regard, 5 was converted to piperidinol 13 and piperidinone 15, that may be further elaborated for the syntheses of (+-desoxoprosophylline (1 and deoxymannojirimycin (3 or D-mannolactam (4, respectively.

  2. 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...

  3. 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

  4. A Concise Synthesis of the Erythrina Alkaloid 3–Demethoxyerythratidinone via Combined Rhodium Catalysis

    Science.gov (United States)

    Joo, Jung Min; David, Ramoncito A.; Yuan, Yu; Lee, Chulbom

    2010-01-01

    The total synthesis of the erythrina alkaloid 3–demethoxyerythratidinone has been achieved via a strategy based on combined rhodium catalysis. The catalytic tandem cyclization effected by the interplay of alkynyl and vinylidene rhodium species allows for efficient access to the A and B rings of the tetracyclic erythrinane skeleton in a single step. The synthesis also features rapid preparation of the requisite precursor for the double ring closure and thus has been completed in only 7 total steps in 41% overall yield. PMID:21090648

  5. Knorr-Rabe partial reduction of pyrroles: Application to the synthesis of indolizidine alkaloids

    Directory of Open Access Journals (Sweden)

    Ryan John H

    2008-01-01

    Full Text Available Abstract Background The Birch reduction of electron rich pyrroles does not occur readily. However, dissolving metal reduction with zinc under acidic conditions gives 3-pyrrolines (2,5-dihydropyrroles in reasonable yield. This dissolving metal reduction was first reported by Knorr and Rabe in 1901 but since then has only been reported for the reduction of electron rich pyrroles. Results The partial reduction of bicyclic α-ketopyrrole derivatives has been performed under dissolving metal conditions with zinc and hydrochloric acid to give excellent yields of hexahydroindolizidines. This reduction method has been utilised for the diastereoselective synthesis of 5-alkylindolizidines and the stereoselectivity obtained is opposite to that of catalytic hydrogenation. Conclusion An efficient stereoselective synthesis of indolizidine alkaloids has been developed from α-ketopyrrole intermediates using a modified version of Knorr and Rabe's pyrrole reduction.

  6. In Silico Screening and Designing Synthesis of Cinchona Alkaloids Derivatives as Potential Anticancer

    Directory of Open Access Journals (Sweden)

    Muhammad Hanafi

    2017-06-01

    Full Text Available P-glycoprotein (P-gp resistance in cancer cells decreases intracellular accumulation of various anticancer drugs. This multidrug resistance (MDR protein can be modulated by a number of non-cytotoxic drugs. We have screened 30 chincona alkaloids derivatives as a potent P-gp inhibitor agent in silico. Hereby, we report the highest potential inhibitions of P-gp is Cinchonidine isobutanoate through molecular docking approach. with affinity energy -8.6 kcal/mol and inhibition constant, Ki is 4.89 x 10-7 M. Cinchonidine isobutanoate is also known has molecular weight below 500, Log P value 3.5, which is indicated violation free of Lipinski`s rule of five. Thus, Cinchonidine isobutanoate is the most potent compound as anticancer compare to other Cinchona alkaloids. Ultimately, we design Cinchonidine isobutanoate for further lead synthesis by using DBSA, act as a combined Brønsted acid-surfactant-catalyst (BASC to obtain high concentration of organic product by forming micellar aggregates which is very powerful catalytic application in water environment.

  7. 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...

  8. Synthesis and Biological Evaluation of Novel 3-Alkylpyridine Marine Alkaloid Analogs with Promising Anticancer Activity

    Directory of Open Access Journals (Sweden)

    Alessandra Mirtes Marques Neves Gonçalves

    2014-07-01

    Full Text Available Cancer continues to be one of the most important health problems worldwide, and the identification of novel drugs and treatments to address this disease is urgent. During recent years, marine organisms have proven to be a promising source of new compounds with action against tumoral cell lines. Here, we describe the synthesis and anticancer activity of eight new 3-alkylpyridine alkaloid (3-APA analogs in four steps and with good yields. The key step for the synthesis of these compounds is a Williamson etherification under phase-transfer conditions. We investigated the influence of the length of the alkyl chain attached to position 3 of the pyridine ring on the cytotoxicity of these compounds. Biological assays demonstrated that compounds with an alkyl chain of ten carbon atoms (4c and 5c were the most active against two tumoral cell lines: RKO-AS-45-1 and HeLa. Micronucleus and TUNEL assays showed that both compounds are mutagenic and induce apoptosis. In addition, Compound 5c altered the cellular actin cytoskeleton in RKO-AS-45-1 cells. The results suggest that Compounds 4c and 5c may be novel prototype anticancer agents.

  9. Cytotoxic 1,3-Thiazole and 1,2,4-Thiadiazole Alkaloids from Penicillium oxalicum: Structural Elucidation and Total Synthesis

    Directory of Open Access Journals (Sweden)

    Zheng Yang

    2016-02-01

    Full Text Available Two new thiazole and thiadiazole alkaloids, penicilliumthiamine A and B (2 and 3, were isolated from the culture broth of Penicillium oxalicum, a fungus found in Acrida cinerea. Their structures were elucidated mainly by spectroscopic analysis, total synthesis and X-ray crystallographic analysis. Biological evaluations indicated that compound 1, 3a and 3 exhibit potent cytotoxicity against different cancer cell lines through inhibiting the phosphorylation of AKT/PKB (Ser 473, one of important cancer drugs target.

  10. 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...

  11. Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones

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    Joaquín Tamariz

    2013-08-01

    Full Text Available A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported.

  12. 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

  13. Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids

    OpenAIRE

    Lathrop, Stephen; Movassaghi, Mohammad

    2013-01-01

    We describe the first application of our methodology for heterodimerization via diazene fragmentation towards the total synthesis of (−)-calycanthidine, meso-chimonanthine, and (+)-desmethyl-meso-chimonanthine. Our syntheses of these alkaloids feature an improved route to C3a-aminocyclotryptamines, an enhanced method for sulfamide synthesis and oxidation, in addition to a late-stage diversification leading to the first enantioselective total synthesis of (+)-desmethyl-meso-chimonanthine and i...

  14. Total Synthesis of Zoanthamine Alkaloids, Part 2. Construction of the C1-C5, C6-C10 and C11-C24 Fragments of Zoanthamine

    DEFF Research Database (Denmark)

    Tanner, David Ackland; Tedenborg, Lars; Somfai, Peter

    1997-01-01

    This paper describes the construction of three key intermediates for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C1-C5, C6-C10 and C11-C24 fragments of the target molecule, are synthesised efficiently form (R)-hydroxymethyl-butyrolac......This paper describes the construction of three key intermediates for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C1-C5, C6-C10 and C11-C24 fragments of the target molecule, are synthesised efficiently form (R...

  15. 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.

  16. 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.

  17. Total Synthesis of the Spirocyclic Oxindole Alkaloids Corynoxine, Corynoxine B, Corynoxeine, and Rhynchophylline

    NARCIS (Netherlands)

    Wanner, M.J.; Ingemann, S.; van Maarseveen, J.H.; Hiemstra, H.

    2013-01-01

    Racemic total syntheses of four spirocyclic oxindole alkaloids are reported. The general starting material was an N-2-butenylated 2-hydroxytryptamine, which underwent a base-mediated Mannich spirocyclisation with a functionalised aldehyde to generate the C-ring. The second key step was a

  18. Synthesis of marine-derived 3-alkylpyridinium alkaloids with potent antiprotozoal activity

    NARCIS (Netherlands)

    Rodenko, B.; Al-Salabi, M.I.; Teka, I.A.; Ho, W.; El-Sabbagh, N.; Ali, J.A.M.; Ibrahim, H.M.S.; Wanner, M.J.; Koomen, G.J.; de Koning, H.P.

    2011-01-01

    Given the pressing need for new antiprotozoal drugs without cross-resistance with current (failing) chemotherapy, we have explored 3-tridecylpyridinium alkaloids (3TPAs), derivatives of viscosamine, as antiparasitic agents. We have developed a simple synthetic route toward viscosamine and related

  19. Total Synthesis of Zoanthamine Alkaloids, Part 2. Construction of the C1-C5, C6-C10 and C11-C24 Fragments of Zoanthamine

    DEFF Research Database (Denmark)

    Tanner, David Ackland; Tedenborg, Lars; Somfai, Peter

    1997-01-01

    This paper describes the construction of three key intermediates for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C1-C5, C6-C10 and C11-C24 fragments of the target molecule, are synthesised efficiently form (R...

  20. A concise synthesis of (R)-Bgugaine, a pyrrolidine alkaloid from Arisarum vulgare

    Digital Repository Service at National Institute of Oceanography (India)

    Majik, M.S.; Parameswaran, P.S.; Tilve, S.G.

    and conversion of N-carboethoxy group to N-methyl. Keywords: pyrrolidine alkaloids, bgugaine, Wittig reaction Nitrogen containing heterocycles including pyrrolidines, piperidines and related compounds, include important biologically active compounds 1.... 18 The necessary manipulation for the conversion of aldehyde group to tetradecane chain involved application of the Wittig reaction followed by reduction of the double bond and reduction of carboethoxy group to methyl. Thus, freshly...

  1. Towards the Shell Biorefinery: Sustainable Synthesis of the Anticancer Alkaloid Proximicin A from Chitin.

    Science.gov (United States)

    Sadiq, Alejandro D; Chen, Xi; Yan, Ning; Sperry, Jonathan

    2018-02-09

    A shell biorefinery would involve fractionation of crustacean shells and incorporation of the components into value-added products, particularly those that contain nitrogen. In a proof-of-concept study that validates this concept, the anticancer alkaloid proximicin A has been synthesized from the chitin-derived platform chemical 3-acetamido-5-acetylfuran (3A5AF). This study accentuates the leading role chitin is likely to play in the sustainable production of nitrogen-containing fine chemicals that are not directly attainable from lignocellulose. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  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. 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.

  4. Synthesis and Fungicidal Activity of β-Carboline Alkaloids and Their Derivatives

    Directory of Open Access Journals (Sweden)

    Zhibin Li

    2015-07-01

    Full Text Available A series of β-Carboline derivatives were designed, synthesized, and evaluated for their fungicidal activities in this study. Several derivatives electively exhibited fungicidal activities against some fungi. Especially, compound F5 exhibited higher fungicidal activity against Rhizoctonia solani (53.35% than commercial antiviral agent validamycin (36.4%; compound F16 exhibited high fungicidal activity against Oospora citriaurantii ex Persoon (43.28%. Some of the alkaloids and their derivatives (compounds F4 and F25 exhibited broad-spectrum fungicidal activity. Specifically, compound F4 exhibited excellent high broad-spectrum fungicidal activity in vitro, and the curative and protection activities against P. litchi in vivo reached 92.59% and 59.26%, respectively. The new derivative, F4, with optimized physicochemical properties, obviously exhibited higher activities both in vitro and in vivo; therefore, F4 may be used as a new lead structure for the development of fungicidal drugs.

  5. One-Pot Synthesis of Novel Chiral β-Amino Acid Derivatives by Enantioselective Mannich Reactions Catalyzed by Squaramide Cinchona Alkaloids

    Directory of Open Access Journals (Sweden)

    Kankan Zhang

    2013-05-01

    Full Text Available An efficient one-pot synthesis of novel β-amino acid derivatives containing a thiadiazole moiety was developed using a chiral squaramide cinchona alkaloid as organocatalyst. The reactions afforded chiral β-amino acid derivatives in moderate yields and with moderate to excellent enantioselectivities. The present study demonstrated for the first time the use of a Mannich reaction catalyzed by a chiral bifunctional organocatalyst for the one-pot synthesis of novel β-amino acid derivatives bearing a 1,3,4-thiadiazole moiety on nitrogen.

  6. An unexpected reaction pathway in the synthesis of the ABCE framework of strychnine-type alkaloids - A multidisciplinary study

    Science.gov (United States)

    Šoral, Michal; Markus, Jozef; Doháňošová, Jana; Šoralová, Stanislava; Dvoranová, Dana; Chyba, Andrej; Moncol, Ján; Berkeš, Dušan; Liptaj, Tibor

    2017-01-01

    Acid-catalyzed cyclization of spirocyclic 1‧-benzyl-2‧-(prop-2-en-1-yl)spiro[indole-3,3‧-pyrrolidine]-5‧-one (1) was performed. The pentacyclic product of Povarov-like imino-Diels-Alder reaction was isolated in high yield instead of expected tetracyclic aza-Prins intermediate. The unusual exotic alkaloid-type structure of the resulting molecule 2 was unambiguously confirmed by a detailed NMR analysis using a set of 2D NMR spectra including an INADEQUATE experiment. The relative configuration of 2 was predicted from the synthesis mechanism and DFT geometry calculations and independently confirmed using NOESY and residual dipolar coupling (RDC) assisted NMR analysis in stretched crosslinked polystyrene gels. The reversibility of the cycloaddition in aprotic solvents was observed. A new reaction pathway yielding a rare 6-5-5-5 tetracyclic spiroindoline 3 was suggested. The relative configuration within the tetracyclic framework was ultimately proved using Single-crystal X-ray diffraction analysis of compound 4.

  7. 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.

  8. Engineering an enantioselective amine oxidase for the synthesis of pharmaceutical building blocks and alkaloid natural products.

    Science.gov (United States)

    Ghislieri, Diego; Green, Anthony P; Pontini, Marta; Willies, Simon C; Rowles, Ian; Frank, Annika; Grogan, Gideon; Turner, Nicholas J

    2013-07-24

    The development of cost-effective and sustainable catalytic methods for the production of enantiomerically pure chiral amines is a key challenge facing the pharmaceutical and fine chemical industries. This challenge is highlighted by the estimate that 40-45% of drug candidates contain a chiral amine, fueling a demand for broadly applicable synthetic methods that deliver target structures in high yield and enantiomeric excess. Herein we describe the development and application of a "toolbox" of monoamine oxidase variants from Aspergillus niger (MAO-N) which display remarkable substrate scope and tolerance for sterically demanding motifs, including a new variant, which exhibits high activity and enantioselectivity toward substrates containing the aminodiphenylmethane (benzhydrylamine) template. By combining rational structure-guided engineering with high-throughput screening, it has been possible to expand the substrate scope of MAO-N to accommodate amine substrates containing bulky aryl substituents. These engineered MAO-N biocatalysts have been applied in deracemization reactions for the efficient asymmetric synthesis of the generic active pharmaceutical ingredients Solifenacin and Levocetirizine as well as the natural products (R)-coniine, (R)-eleagnine, and (R)-leptaflorine. We also report a novel MAO-N mediated asymmetric oxidative Pictet-Spengler approach to the synthesis of (R)-harmicine.

  9. Synthetic transformations of isoquinoline alkaloids. Synthesis of dihydrothebaine-hydroquinone derivatives

    International Nuclear Information System (INIS)

    Bauman, V.T.; Shul'ts, Eh. Eh.; Shakirov, M.M.; Tolstikov, G.A.

    2007-01-01

    Synthesis of new 6,14-endo-ethenodihydrothebaine-hydroquinone derivatives is carried through the introduction of iodine in molecule of the compound by means of iodine chloride or iodine in the presence of cerium-ammonium nitrate. 1-Iodine-5,14-endo-etheno-7,8-(1-acetoxy-4-hydroxybenzo)dihydrothebaine (yield 57%), 1-iodine-6,14-endo-etheno-7,8-(1,4-hydroquinono)dihydrothebaine (yield 13%) and 1-iodine-5'-chlorine-6,14-endo-etheno-7,8-(1,4-hydroquinono)dihydrothebaine (yield 11%) are separated as products of the reaction. Structure, molecular mass and element composition of iodination products were established on the basis of analysis of NMR spectra and mass spectroscopy, course of the reaction was controlled by TLC method [ru

  10. 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.

  11. Studies toward the synthesis of palhinine lycopodium alkaloids: a Morita-Baylis-Hillman/intramolecular Diels-Alder approach.

    Science.gov (United States)

    Sizemore, Nicholas; Rychnovsky, Scott D

    2014-02-07

    A synthetic route to the isotwistane core of palhinine lycopodium alkaloids is described. A Morita-Baylis-Hillman/intramolecular Diels-Alder (IMDA) strategy sets the vicinal all-carbon quaternary centers present in this family of natural products. The regioselectivity of the IMDA reaction is dictated by the conditions employed for silyl enol ether formation, with one set of conditions providing the core of cardionine and alternate conditions generating the desired isotwistane core of isopalhinine.

  12. Flexible synthetic routes to poison-frog alkaloids of the 5,8-disubstituted indolizidine-class I: synthesis of common lactam chiral building blocks and application to the synthesis of (--203A, (--205A, and (--219F

    Directory of Open Access Journals (Sweden)

    Spande Thomas F

    2007-09-01

    Full Text Available Abstract Background The 5,8-disubstituted indolizidines are the largest class of poison-frog alkaloids found in anuran skin, and are of considerable interest because of their inhibitory effects on the neuronal nicotinic acetylcholine receptors. Many synthetic strategies for the construction of this nucleus have been reported: however, a flexible route has not been reported to date. Results Synthesis of lactam chiral building blocks for the flexible synthesis of the title alkaloids has been achieved using a Michael-type conjugate addition reaction to a chiral cyclic enamine ester as the key step in constructing the trisubstituted piperidine ring system. To demonstrate the usefulness of these chiral building blocks, syntheses of (--203A, (--205A from 1, and (--219F from 2 have been achieved. Conclusion The total synthesis of (--203A, (--205A, and (--219F was achieved, and the absolute stereochemistry of natural 203A was determined to be 5S, 8R, 9S. In addition, the relative stereochemistry of natural 219F was determined.

  13. 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.

  14. Direct Synthesis of Protoberberine Alkaloids by Rh-Catalyzed C-H Bond Activation as the Key Step.

    Science.gov (United States)

    Jayakumar, Jayachandran; Cheng, Chien-Hong

    2016-01-26

    A one-pot reaction of substituted benzaldehydes with alkyne-amines by a Rh-catalyzed C-H activation and annulation to afford various natural and unnatural protoberberine alkaloids is reported. This reaction provides a convenient route for the generation of a compound library of protoberberine salts, which recently have attracted great attention because of their diverse biological activities. In addition, pyridinium salt derivatives can also be formed in good yields from α,β-unsaturated aldehydes and amino-alkynes. This reaction proceeds with excellent regioselectivity and good functional group compatibility under mild reaction conditions by using O2 as the oxidant. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  15. 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...

  16. 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

  17. 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.

  18. One pot synthesis of new poly(vinyl alcohol) blended natural polymer based magnetic hydrogel beads: Controlled natural anticancer alkaloid delivery system.

    Science.gov (United States)

    Kesavan, Mookkandi Palsamy; Ayyanaar, Srinivasan; Lenin, Nayagam; Sankarganesh, Murugesan; Dhaveethu Raja, Jeyaraj; Rajesh, Jegathalaprathaban

    2018-02-01

    Facile one-pot synthesis has been demonstrated for new biocompatible and dual responsive magnetic iron oxide nanoparticles cross-linked poly(vinyl alcohol) (PVA) blended natural polymer chitosan (CS) based hydrogel beads (mCS-PVA) as a controlled natural anticancer alkaloid Luotonin A (LuA) delivery system. The prepared magnetic hydrogel beads were characterized using powder X-ray diffraction measurement, Fourier transform-infrared spectroscopy, scanning electron microscopy, energy dispersive X-ray spectroscopy, and vibrating sample magnetometer. The magnetic hydrogel beads are exhibited significant water retention and follow the second order kinetic model in swelling study. The swelling ratio of the magnetic gel beads increased by the addition of PVA and showed a maximum swelling ratio of 40.83 ± 1.01 g/g and follows non-Fickian water transport mechanism. Stimuli responsive mCS and mCS-PVA hydrogel beads functionalized with LuA is demonstrated for controlled release at physiological pH and under magnetic field. The magnetic hydrogel beads show highest LuA releasing efficacy at acidic medium (pH = 5.0) with maximum efficiency of 73.33 ± 1.44%. This efficacy may also be tuned by altering the external magnetic field as well as the weight percentage (wt %) of polyethylene glycol. It is clearly that the newly produced magnetic hydrogel beads can be served as an effective intestinal LuA delivery system. © 2017 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 106A: 543-551, 2018. © 2017 Wiley Periodicals, Inc.

  19. 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

  20. The synthesis of 3H-putrescine and subsequent biosynthesis of 3H-jacobine, a pyrrolizidine alkaloid from Senecio jacobaea

    International Nuclear Information System (INIS)

    Reed, R.L.; Buhler, D.R.; Oregon State Univ., Corvallis

    1988-01-01

    A new method was developed for the preparation of tritiated putrescine dihydrochloride ([2,3- 3 H]-1,4-diaminobutane dihydro-chloride) from succinonitrile (1,4-butanedinitrile) and 3 H 2 O, with a radiochemical yield of 16%. Tritiated jacobine and other pyrrolizidine alkaloids were then biosynthesized in Senecio jacobaea using 3 H-putrescine-2HCl as the precursor with a radiochemical yield of 0.9% into total pyrrolizidine alkaloids. Jacobine accounted for 36% of the total. This synthetic method provides a relatively inexpensive source for the preparation of these labelled compounds. (author)

  1. 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.

  2. 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.

  3. 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

  4. 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...

  5. 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...

  6. Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Amino Acids

    Directory of Open Access Journals (Sweden)

    Carmen Nájera

    2004-04-01

    Full Text Available Alkaloids such as cinchonidine, quinine and N-methylephedrine have been N-alkylated using polymeric benzyl halides or co-polymerized and then N-alkylated, thus affording a series of polymer-supported chiral ammonium salts which have been employed as phase-transfer catalysts in the asymmetric benzylation of an N-(diphenylmethyleneglycine ester. These new polymeric catalysts can be easily recovered by simple filtration after the reaction and reused. The best ee’s were achieved when Merrifield resin-anchored cinchonidinium ammonium salts were employed.

  7. Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (--209B, (--231C, (--233D, (--235B", (--221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors

    Directory of Open Access Journals (Sweden)

    Garraffo H Martin

    2007-09-01

    Full Text Available Abstract Background The 5,8-disubstituted indolizidines constitute the largest class of poison-frog alkaloids. Some alkaloids have been shown to act as noncompetitive blockers at nicotinic acetylcholine receptors but the proposed structures and the biological activities of most of the 5,8-disubstituted indolizidines have not been determined because of limited supplies of the natural products. We have therefore conducted experiments to confirm proposed structures and determine biological activities using synthetic compounds. Recently, we reported that one of this class of alkaloids, (--235B', acts as a noncompetitive antagonist for α4β2 nicotinic receptors, and its sensitivity is comparable to that of the classical competitive antagonist for this receptor, dihydro-β-erythroidine. Results The enantioselective syntheses of (--209B, (--231C, (--233D, (--235B", (--221I, and what proved to be an epimer of natural 193E, starting from common chiral lactams have been achieved. When we performed electrophysiological recordings to examine the effects of the synthetic alkaloids on two major subtypes of nicotinic receptors (α4β2 and α7 expressed in Xenopus laevis oocytes, (--231C effectively blocked α4β2 receptor responses (IC50 value, 1.5 μM with a 7.0-fold higher potency than for blockade of α7 receptor responses. In contrast, synthetic (--221I and (--epi-193E were more potent in blocking α7 receptor responses (IC50 value, 4.4 μM and 9.1 μM, respectively than α4β2 receptor responses (5.3-fold and 2.0-fold, respectively. Conclusion We achieved the total synthesis of (--209B, (--231C, (--233D, (--235B", (--221I, and an epimer of 193E starting from common chiral lactams, and the absolute stereochemistry of natural (--233D was determined. Furthermore, the relative stereochemistry of (--231C and (--221I was also determined. The present asymmetric synthesis of the proposed structure for 193E revealed that the C-8 configuration of natural 193E

  8. CNS active ergot alkaloid dihydro derivatives. Tritium labelling and characterization

    International Nuclear Information System (INIS)

    Egan, J.A.; Nugent, R.P.; Filer, C.N.

    2016-01-01

    The ergot alkaloids are an important class of medicinally useful substances and this report describes the high specific activity tritium labelling of two dihydro derivatives; namely, dihydroergotamine and dihydrobromocriptine. The former was prepared by the direct tritiation of ergotamine itself. However, efforts to perform an analogous direct tritiation on bromocriptine were unsuccessful and a multistep synthesis was required. (author)

  9. 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.

  10. 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...

  11. 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.

  12. Concise synthesis of the hasubanan alkaloid (±)-cepharatine A using a Suzuki coupling reaction to effect o,p-phenolic coupling.

    Science.gov (United States)

    Magnus, Philip; Seipp, Charles

    2013-09-20

    Suzuki coupling of 10 and 11 resulted in 9, which was O-alkylated to provide 12. Treatment of 12 with CsF in DMF resulted in the formation of the completed core structure 13 in a single step. Reductive amination of 13 completed the synthesis of (±)-cepharatine A, 4.

  13. 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.

  14. 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.

  15. 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.

  16. Combining the [2,3] Sigmatropic Rearrangement and Ring-Closing Metathesis Strategies for the Synthesis of Spirocyclic Alkaloids. A Short and Efficient Route to (+/-)-Perhydrohistrionicotoxin

    DEFF Research Database (Denmark)

    Tanner, David Ackland; Hagberg, Lars; Poulsen, Anders

    1999-01-01

    This paper describes the use of selenium-based [2,3] sigmatropic rearrangement in combination with ruthenium-catalyzed ring-closing metathesis (RCM) for the synthesis of azaspiro ring systems, as exemplified by the reactions of model substrates 5 and 6. The methodology has been applied to a short...... is potentially enantioselective, and key steps were the [2,3] sigmatropic rearrangement of 11 to 12 via the corresponding allylic selenide (86% yield) and ruthenium-catalyzed RCM of 13 to 14 (80%). (C) 1999 Elsevier Science Ltd. All rights reserved....

  17. 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.)

  18. 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.

  19. 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.

  20. 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.

  1. 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)

  2. 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...

  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. 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.

  5. 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

  6. 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.

  7. 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.

  8. 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)

  9. 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)

  10. 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 ...

  11. 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

  12. 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.

  13. 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

  14. 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

  15. 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)

  16. 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)

  17. Alcalóides alquilpiridínicos de esponjas marinhas Alkylpyridine alkaloids from marine sponges

    Directory of Open Access Journals (Sweden)

    Adaíla M. P. Almeida

    1997-04-01

    Full Text Available The chemistry of alkylpyridine alkaloids originating from marine sponges is comprehensively reviewed, with emphasis on their natural occurrence, methods for their isolation, spectroscopic characterization, biological activities e chemical synthesis. A likely chemotaxonomic role is suggested, as markers for sponges of the Order Haplosclerida (Demospongiae.

  18. 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

  19. 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)

  20. 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)

  1. 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.

  2. 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.

  3. A Short Synthetic Route to the Calystegine Alkaloids

    DEFF Research Database (Denmark)

    Skaanderup, Philip Robert; Madsen, Robert

    2003-01-01

    An efficient strategy is described for the synthesis of enantiopure calystegine alkaloids. The key step employs a zinc-mediated fragmentation of benzyl-protected methyl 6-iodo-glycosides followed by in situ formation of the benzyl imine and Barbier-type allylation with zinc, magnesium, or indium...... metal. Stereochemistry in the pivotal allylation is controlled by the choice of the metal. The functionalized 1,8-nonadienes, thus formed, are converted into cycloheptenes by ring-closing metathesis. Regioselective hydroboration and oxidation give the corresponding cycloheptanones, which are deprotected...

  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. 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.

  6. 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

  7. 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.

  8. 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

  9. 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.

  10. A novel synthesis of octahydropyrido[3,2-c]carbazole framework of aspidospermidine alkaloids and a combined computational, FT-IR, NMR, NBO, NLO, FMO, MEP study of the cis-4a-Ethyl-1-(2hydroxyethyl)-2,3,4,4a,5,6,7,11c-octahydro-1H-pyrido[3,2-c]carbazole

    Science.gov (United States)

    Uludağ, Nesimi; Serdaroğlu, Goncagul; Yinanc, Abdullah

    2018-06-01

    In this study, we performed a novel synthesis of the octahydropyrido[3,2-c]carbazole derivative 6 from 1 in five steps with a 34% overall yield. We also developed a unique compound 2 by a cyclization reaction from the cyanoethylation of compound 1, which is an intermediate step in the synthesis of Aspidospermidine. The parent compound of Aspidospermidine alkaloids, comprise a large family of diverse structures. As a result, we obtained octahydropyrido[3,2-c]carbazole (6)and the proposed method may be applicable to other alkaloids. All quantum chemical calculations of the cis-4a-Ethyl-1-(2-hydroxyethyl)-2,3,4,4a,5,6,7,11c-octahydro-1H-pyrido[3,2-c]carbazole have been performed with the DFT/B3LYP and HF methods by using the Gaussian 09W software package. The most stable conformer obtained from the Potential Energy Surface (PES) scan analysis at the B3LYP/6-31G** level of theory in the gas phase was used as the starting structure of the title compound to further computational analysis. The Natural Bond Orbital (NBO) and NLO analyses were performed to evaluate the intra-molecular interactions contributing to the molecular stability and to predict the optical properties of the title compound, respectively. Gauge-Independent Atomic Orbital (GIAO) approach was used to determine the 1H and 1C NMR chemical shifts of the title compound by subtracting the shielding constants of TMS at both methods. The calculated vibrational frequencies of the title compound were assigned by using the VEDA program and were scaled down by using the scaling factor 0.9668 for B3LYP/6-311++G(d, p) and 0.9050 for HF/6-311++G(d, p) to improve the calculated vibrational frequencies. The FMO (frontier molecular orbital) analysis was evaluated to predict the chemical and physical properties of the title compound and the HOMO, LUMO, and MEP diagrams were visualized by GaussView 4.1 program to present the reactive site of the title compound.

  11. 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.

  12. A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids

    Directory of Open Access Journals (Sweden)

    Remuson Roland

    2007-10-01

    Full Text Available Abstract This review relates all the results that we obtained in the field of the total synthesis of indolizidine and quinolizidine alkaloids using a strategy of the addition of an allylsilane on an N-acyliminium ion. In this paper, we describe the synthesis of racemic indolizidine 167B and chiral indolizidines: (--indolizidines 167B, 195B, 223AB, (+-monomorine, (--(3R,5S,8aS-3-butyl-5-propylindolizidine and (--dendroprimine. Next, we relate the synthesis that we have developed in the quinolizidines field: (±-myrtine and epimyrtine, (±-lasubines I and II and chiral quinolizidines: (+-myrtine, (--epimyrtine, (--lasubines I and II and (+-subcosine II.

  13. 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 ...

  14. 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

  15. 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.

  16. 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 ...

  17. A concise synthesis of the cortistatin core

    OpenAIRE

    Dai, Mingji; Danishefsky, Samuel J.

    2008-01-01

    We describe a concise and convergent route to the core matrix of the cortistatin steroidal alkaloids. The salient features of the synthesis are the Snieckus cascade methodology and the Masamune alkylative dearomatization. This chemistry lends itself to a total synthesis of the cortistatins and to the development of a SAR program based on diverted total synthesis.

  18. 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

  19. Amaryllidaceae Alkaloids as Potential Glycogen Synthase Kinase-3β Inhibitors

    Directory of Open Access Journals (Sweden)

    Daniela Hulcová

    2018-03-01

    Full Text Available Glycogen synthase kinase-3β (GSK-3β is a multifunctional serine/threonine protein kinase that was originally identified as an enzyme involved in the control of glycogen metabolism. It plays a key role in diverse physiological processes including metabolism, the cell cycle, and gene expression by regulating a wide variety of well-known substances like glycogen synthase, tau-protein, and β-catenin. Recent studies have identified GSK-3β as a potential therapeutic target in Alzheimer´s disease, bipolar disorder, stroke, more than 15 types of cancer, and diabetes. GSK-3β is one of the most attractive targets for medicinal chemists in the discovery, design, and synthesis of new selective potent inhibitors. In the current study, twenty-eight Amaryllidaceae alkaloids of various structural types were studied for their potency to inhibit GSK-3β. Promising results have been demonstrated by alkaloids of the homolycorine-{9-O-demethylhomolycorine (IC50 = 30.00 ± 0.71 µM, masonine (IC50 = 27.81 ± 0.01 μM}, and lycorine-types {caranine (IC50 = 30.75 ± 0.04 μM}.

  20. 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.

  1. A Concise Total Synthesis of S-(+)-Tylophorine

    Institute of Scientific and Technical Information of China (English)

    JIN,Zhong; WANG,Qing-Min; LI,Hao; LIU,Yu-Xiu; LI,Shi-Pu; HUANG,Run-Qiu

    2004-01-01

    @@ Phenanthroindolizidine alkaloids, which exhibit extensively biological properties, are widely present at various plants of the Asclepiadaceae family.[1] The significantly biological importance of these natural products has attracted considerable synthetic efforts.[2] We herein report an efficiently asyinmetric synthesis of S-(+)-tylophorine (1), as a typically representative alkaloids.

  2. The biology and chemistry of the zoanthamine alkaloids.

    Science.gov (United States)

    Behenna, Douglas C; Stockdill, Jennifer L; Stoltz, Brian M

    2008-01-01

    Marine natural products have long played an important role in natural products chemistry and drug discovery. Mirroring the rich variety and complicated interactions of the marine environment, the substances isolated from sea creatures tend to be incredibly diverse in both molecular structure and biological activity. The natural products isolated from the polyps of marine zoanthids are no exception. The zoanthamine alkaloids, the first of which were isolated over 20 years ago, are of particular interest to the synthetic community because they feature a novel structural framework and exhibit a broad range of biological activities. In this Review, we summarize the major contributions to understanding the zoanthamine natural products with regard to their isolation and structure determination, as well as studies on their biological activity and total synthesis.

  3. 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.

  4. 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.

  5. 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.

  6. 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)

  7. 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.

  8. 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)

  9. 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.

  10. 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)

  11. 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.

  12. 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.

  13. 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.

  14. 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

  15. 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...

  16. Studies in the stereoselective synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines

    OpenAIRE

    Berg, Michael Arthur George

    1992-01-01

    Isoquinoline alkaloids and analogs play an important role in today's pharmaceutical industry. The need to synthesize single stereoisomers of these alkaloids is important. Many times only a single stereoisomer exhibits the desired activity, while other stereoisomers of the alkaloid exhibit undesired side effects. The stereoselective synthesis of 1, 1-disubstituted 1,2,3,4- tetrahydroisoquinolines using Reissert compound chemistry containing chiral acyl auxiliaries was studied with the ultimate...

  17. Accumulation of Monoterpenoid Indole Alkaloids in Periwinkle Seedlings ("Catharanthus roseus") as a Model for the Study of Plant-Environment Interactions

    Science.gov (United States)

    Miranda-Ham, Maria de Lourdes; Islas-Flores, Ignacio; Vazquez-Flota, Felipe

    2007-01-01

    Alkaloids are part of the chemical arsenal designed to protect plants against an adverse environment. Therefore, their synthesis and accumulation are frequently induced in response to certain environmental conditions and are mediated by chemical signals, which are formed as the first responses to the external stimulus. A set of experiments using…

  18. 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.

  19. 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)

  20. 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.

  1. 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.

  2. 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

  3. 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)

  4. 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)

  5. 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.

  6. 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)

  7. 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....

  8. 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.

  9. 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)

  10. 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.

  11. Expedient preparation of nazlinine and a small library of indole alkaloids using flow electrochemistry as an enabling technology.

    Science.gov (United States)

    Kabeshov, Mikhail A; Musio, Biagia; Murray, Philip R D; Browne, Duncan L; Ley, Steven V

    2014-09-05

    An expedient synthesis of the indole alkaloid nazlinine is reported. Judicious choice of flow electrochemistry as an enabling technology has permitted the rapid generation of a small library of unnatural relatives of this biologically active molecule. Furthermore, by conducting the key electrochemical Shono oxidation in a flow cell, the loading of electrolyte can be significantly reduced to 20 mol % while maintaining a stable, broadly applicable process.

  12. Induction of Morphological Changes in Human Embryo Liver Cells by the Pyrrolizidine Alkaloid Lasiocarpine

    Science.gov (United States)

    Armstrong, Sylvia J.; Zuckerman, A. J.; Bird, R. G.

    1972-01-01

    The pyrrolizidine alkaloids have been implicated in the aetiology of liver disease in man and in animals. Studies of the effects of lasiocarpine indicate that they have several and perhaps independent effects on human liver cells in culture. These may be summarized as follows: 1. Nuclear and nucleolar changes which are probably related to the alkylation of DNA and ensuing inhibition of nucleic acid and protein synthesis. 2. The induction of possible chromosomal damage and mutation. 3. A generalized reduction of the metabolic activities of the cells due to membrane and mitochondrial damage, and to alkylation and inactivation of cell enzymes and proteins. 4. A long-term inhibition of mitosis leading to the formation of giant cells (“megalocytes”). The morphological effects induced by a number of the pyrrolizidine alkaloids were very similar but the pattern of metabolic changes varied somewhat. It is believed that the hepatotoxic effects are not due to the pyrrolizidine alkaloids themselves but to metabolic derivatives formed by the cell. ImagesFigs. 3-5Figs. 1-2 PMID:5032090

  13. 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.

  14. 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.

  15. 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

  16. Geographic variation in alkaloid production in Conium maculatum populations experiencing differential herbivory by Agonopterix alstroemeriana.

    Science.gov (United States)

    Castells, Eva; Berhow, Mark A; Vaughn, Steven F; Berenbaum, May R

    2005-08-01

    Conium maculatum, a Eurasian weed naturalized in North America, contains high concentrations of piperidine alkaloids that act as chemical defenses against herbivores. C. maculatum was largely free from herbivory in the United States, until approximately 30 yr ago, when it was reassociated via accidental introduction with a monophagous European herbivore, the oecophorid caterpillar Agonopterix alstroemeriana. At present, A. alstroemeriana is found in a continuum of reassociation time and intensities with C. maculatum across the continent; in the Pacific Northwest, A. alstroemeriana can cause severe damage, resulting in some cases in complete defoliation. Studies in biological control and invasion biology have yet to determine whether plants reassociated with a significant herbivore from the area of indigeneity increase their chemical defense investment in areas of introduction. In this study, we compared three locations in the United States (New York, Washington, and Illinois) where C. maculatum experiences different levels of herbivory by A. alstroemeriana to determine the association between the intensity of the interaction, as measured by damage, and chemical defense production. Total alkaloid production in C. maculatum was positively correlated with A. alstroemeriana herbivory levels: plants from New York and Washington, with higher herbivory levels, invested two and four times more N to alkaloid synthesis than did plants from Illinois. Individual plants with lower concentrations of alkaloids from a single location in Illinois experienced more damage by A. alstroemeriana, indicative of a preference on the part of the insect for plants with less chemical defense. These results suggest that A. alstroemeriana may act either as a selective agent or inducing agent for C. maculatum and increase its toxicity in its introduced range.

  17. 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...

  18. 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 ...

  19. 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.

  20. 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

  1. 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

  2. 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

  3. 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 ...

  4. 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.

  5. 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.

  6. 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.

  7. Synthesis and Antitumor Activities of Phenanthrene-Based Alkaloids

    Directory of Open Access Journals (Sweden)

    Zhanyou Wang

    2009-12-01

    Full Text Available A series of phenanthrene-based tylophorine derivatives (PBTs were synthesized and their cytotoxic activities against the H460 human large-cell lung carcinoma cell line were evaluated. Among these compounds, N-(3-hydroxy-2,6,7-tri-methoxyphenanthr-9-ylmethyl-L-prolinol (5a, and N-(3-hydroxy-2,6,7-trimethoxy-phenanthr-9-ylmethyl-L-valinol (9 exhibited good activities, with IC50 values of 11.6 and 6.1 mM, respectively.

  8. 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.

  9. 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

  10. 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...

  11. 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...

  12. 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)

  13. 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).

  14. 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)

  15. 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).

  16. A novel alkaloid from Portulaca oleracea L.

    Science.gov (United States)

    Xu, Liang; Ying, Zheming; Wei, Wenjuan; Hao, Dong; Wang, Haibo; Zhang, Wenjie; Li, Cuiyu; Jiang, Mingyue; Ying, Xixiang; Liu, Jing

    2017-04-01

    A novel alkaloid named oleraciamide C (1), with six known compounds, hydroxydihydrobovolide (2), uracil (3), catechol (4), 4-aminophenol (5), vanillic acid (6) as well as 3-hydroxypyridine (7), were isolated from Portulaca oleracea L. Additionally, hydroxydihydrobovolide (2), 4-aminophenol (5), 3-hydroxypyridine (7) were obtained from the plant for the first time. Structure of the new compound was determined using spectroscopic methods including HR-ESI-TOF-MS, 1D and 2D NMR. Others were elucidated through 1 H NMR, 13 C NMR spectra and comparison with literature data. Notably, Compound 1 possessed an unusual bis-substituted eight-membered ring linked with the β-glucopyranose moiety. The cytotoxicity of compound 1 was evaluated against human adipose-derived stem cells (hADSCs) by CCK-8 method.

  17. 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.

  18. A stereoselective synthesis of (+)-physoperuvine using a tandem aza-Claisen rearrangement and ring closing metathesis reaction.

    Science.gov (United States)

    Zaed, Ahmed M; Swift, Michael D; Sutherland, Andrew

    2009-07-07

    A stereoselective synthesis of (+)-physoperuvine, a tropane alkaloid from Physalis peruviana Linne has been developed using a one-pot tandem aza-Claisen rearrangement and ring closing metathesis reaction to form the key amino-substituted cycloheptene ring.

  19. 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.

  20. 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...

  1. 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

  2. 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...

  3. 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

  4. 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 ...

  5. 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...

  6. 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.

  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. 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 ...

  9. 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.

  10. 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

  11. 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...

  12. 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.

  13. 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)

  14. 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.

  15. 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...

  16. 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...

  17. 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.

  18. 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.

  19. Influence of tryptophan and related compounds on ergot alkaloid formation in Claviceps purpurea (FR.) Tul.

    Science.gov (United States)

    Erge, D; Schumann, B; Gröger, D

    1984-01-01

    L-Tryptophan did not exert any influence on peptide alkaloid formation in an ergotamine and in an ergosine-accumulating C. purpurea strain. A different picture was observed in a series of related C. purpurea strains. Tryptophan showed a slight stimulatory effect on the ergotoxine producer Pepty 695/S. A blocked mutant of it, designated as Pepty 695/ch which was able to accumulate secoclavines gave similar results. In a high-yielding elymoclavine strain Pepty 695/e, the progeny of the former one, tryptophan up to a concentration of 25 mM stimulated remarkably clavine biosynthesis. Furthermore, tryptophan could overcome the block of synthesis by inorganic phosphate. Increased specific activities of chanoclavine cyclase but not DMAT synthetase were observed in cultures of strain Pepty 695/e supplemented with tryptophan. 5-Methyltryptophan and bioisosteres of tryptophan were ineffective in alkaloid stimulation. These results are compared with those obtained with the grass ergot strain SD 58 and discussed with the relation to other induction phenomena.

  20. Dendrobium nobile Lindl. alkaloids regulate metabolism gene expression in livers of mice.

    Science.gov (United States)

    Xu, Yun-Yan; Xu, Ya-Sha; Wang, Yuan; Wu, Qin; Lu, Yuan-Fu; Liu, Jie; Shi, Jing-Shan

    2017-10-01

    In our previous studies, Dendrobium nobile Lindl. alkaloids (DNLA) has been shown to have glucose-lowering and antihyperlipidaemia effects in diabetic rats, in rats fed with high-fat diets, and in mice challenged with adrenaline. This study aimed to examine the effects of DNLA on the expression of glucose and lipid metabolism genes in livers of mice. Mice were given DNLA at doses of 10-80 mg/kg, po for 8 days, and livers were removed for total RNA and protein isolation to perform real-time RT-PCR and Western blot analysis. Dendrobium nobile Lindl. alkaloids increased PGC1α at mRNA and protein levels and increased glucose metabolism gene Glut2 and FoxO1 expression. DNLA also increased the expression of fatty acid β-oxidation genes Acox1 and Cpt1a. The lipid synthesis regulator Srebp1 (sterol regulatory element-binding protein-1) was decreased, while the lipolysis gene ATGL was increased. Interestingly, DNLA increased the expression of antioxidant gene metallothionein-1 and NADPH quinone oxidoreductase-1 (Nqo1) in livers of mice. Western blot on selected proteins confirmed these changes including the increased expression of GLUT4 and PPARα. DNLA has beneficial effects on liver glucose and lipid metabolism gene expressions, and enhances the Nrf2-antioxidant pathway gene expressions, which could play integrated roles in regulating metabolic disorders. © 2017 Royal Pharmaceutical Society.

  1. (S-5-ethynyl-anabasine, a novel compound, is a more potent agonist than other nicotine alkaloids on the nematode Asu-ACR-16 receptor

    Directory of Open Access Journals (Sweden)

    Fudan Zheng

    2017-04-01

    Here, we describe the synthesis of a novel agonist, (S-5-ethynyl-anabasine, and show that it is more potent (EC50 0.14 ± 0.01 μM than other nicotine alkaloids on Asu-ACR-16. Agonists acting on ACR-16 receptors have the potential to circumvent drug resistance to anthelmintics, like levamisole, that do not act on the ACR-16 receptors.

  2. Synthesis of 14C-labeled stepholidine

    International Nuclear Information System (INIS)

    Yang Liu; Zhang Xin

    1988-01-01

    L-Tetrahydroprotoberberine (THPB) alkaloids are dopamine-receptor antagonists. Stepholidine has been shown to possess the strongest pharmacological effects among the THPB alkaloids studied. In order to study its metabolism and the mode of action of the drug, a radiolabeled stepholidine was required. We report here the synthesis of 14 C-labeled stepholidine by Mannich condensation of 7-benzyloxy-1-(4-benzyloxy-3-hydroxy-benzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline with ( 14 C)formaldehyde followed by methylation and debensylation in 32% radiochemical yield. (author)

  3. Pyrrolizidine alkaloids from Heliotropium transoxanum Bunge

    Directory of Open Access Journals (Sweden)

    M. R. Delnavazi

    2016-02-01

    Full Text Available Background and objectives: The plants belonging to the genus Heliotropium L. (Boraginaceae are the main sources of toxic pyrrolizidine alkaloids (PAs. In the present study, we have investigated the PAs of the aerial parts of Heliotropium transoxanum Bunge, a perennial species native to Iran. Methods: Silica gel column chromatography and silica gel PTLC were applied for the isolation of PAs present in the total methanol extract of H. transoxanum. The structures of the isolated compounds were identified using 1H-NMR, 13C-NMR and EIMS spectral analyses. Results: Three PAs, heliotrine (1, lasiocarpine (2 and heliotrine N-oxide (3,with known mutagenic and genotoxic properties, were isolated from the aerial parts of H. transoxanum. Conclusion: The results of this study on the presence of toxic PAs in H. transoxanum introduce this herb as a poisonous species and also suggest it as an appropriate source for the isolation of heliotrine and lasiocarpine for further toxicological and pharmacological studies.

  4. Dehydropyrrolizidine Alkaloid Toxicity, Cytotoxicity, and Carcinogenicity

    Directory of Open Access Journals (Sweden)

    Bryan L. Stegelmeier

    2016-11-01

    Full Text Available Dehydropyrrolizidine alkaloid (DHPA-producing plants have a worldwide distribution amongst flowering plants and commonly cause poisoning of livestock, wildlife, and humans. Previous work has produced considerable understanding of DHPA metabolism, toxicity, species susceptibility, conditions, and routes of exposure, and pathogenesis of acute poisoning. Intoxication is generally caused by contaminated grains, feed, flour, and breads that result in acute, high-dose, short-duration poisoning. Acute poisoning produces hepatic necrosis that is usually confirmed histologically, epidemiologically, and chemically. Less is known about chronic poisoning that may result when plant populations are sporadic, used as tisanes or herbal preparations, or when DHPAs contaminate milk, honey, pollen, or other animal-derived products. Such subclinical exposures may contribute to the development of chronic disease in humans or may be cumulative and probably slowly progress until liver failure. Recent work using rodent models suggest increased neoplastic incidence even with very low DHPA doses of short durations. These concerns have moved some governments to prohibit or limit human exposure to DHPAs. The purpose of this review is to summarize some recent DHPA research, including in vitro and in vivo DHPA toxicity and carcinogenicity reports, and the implications of these findings with respect to diagnosis and prognosis for human and animal health.

  5. Advances in vinca-alkaloids: Navelbine.

    Science.gov (United States)

    Marty, M; Extra, J M; Espie, M; Leandri, S; Besenval, M; Krikorian, A

    1989-01-01

    Vinorelbine (Navelbine) is a new semisynthetic vinca alkaloid which chemically differs from vinblastine by substitutions on the catharantine moiety of the molecule. It has shown promising experimental antitumor activity against experimental murine tumors as well as continuous cell lines of human neoplastic origin and human tumor xenografts in nude mice. Acute subacute and chronic toxicity extensively studied in rodents, dogs and primate has shown that hematotoxicity was almost the sole side-effect; neurotoxicity appears very limited. Almost exclusive affinity of NVB for mitotic tubulin and tubulin associated protein accounts for this pattern of toxicity. Phase I and II studies have been conducted in humans. Dose limiting side-effect appears to be neutropenia: the drug is slightly emetogenic, induces little alopecia, almost no neurotoxicity, and no other toxicity. Although preliminary, results of phase II studies already suggest significant activity of NVB in non small lung cancer (33% response rate in 78 evaluable patients), advanced breast cancer (53% response rate in 33 pts without significant chemotherapy for the target progression) and Hodgkin's disease (90% response rate after 4 weekly courses in 31 pts). Thus extensive pharmacological studies and ongoing clinical studies confirm that chemical modifications of the catharantine moiety of vinca alcaloid can lead to active agents with broader spectrum of activity and easily manageable side effects.

  6. 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.

  7. 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.

  8. 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.

  9. 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)

  10. 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.

  11. 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...

  12. One-pot synthesis of 2H-pyrans by indium(III) chloride-catalyzed reactions. efficient synthesis of pyranocoumarins, pyranophenalenones, and pyranoquinolinones

    International Nuclear Information System (INIS)

    Lee, Yong Rok; Kim, Do Hoon; Shim, Jae Jin; Kim, Seog K.; Park, Jung Hag; Cha, Jin Soon; Lee, Chong Soon

    2002-01-01

    An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of α.β-unsaturated aldehydes in moderates yields. This method has been applied to the synthesis of pyranocoumarins, pyranophenaleneones, and pyranoquinolinone alkaloids

  13. One-pot synthesis of 2H-pyrans by indium(III) chloride-catalyzed reactions. efficient synthesis of pyranocoumarins, pyranophenalenones, and pyranoquinolinones

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Yong Rok; Kim, Do Hoon; Shim, Jae Jin; Kim, Seog K.; Park, Jung Hag; Cha, Jin Soon; Lee, Chong Soon [Yeungnam Univ., Kyongsan (Korea, Republic of)

    2002-08-01

    An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of {alpha}.{beta}-unsaturated aldehydes in moderates yields. This method has been applied to the synthesis of pyranocoumarins, pyranophenaleneones, and pyranoquinolinone alkaloids.

  14. THE ALKALOID CYTISINE IN THE CELL CULTURE

    Directory of Open Access Journals (Sweden)

    Gazaliev A.M.

    2012-08-01

    Full Text Available Alkaloids are vegetative establishments of complex and original structure with nitrous heterocycles in the basis. For a long time they drew researchers’ attention because of their unique and specific physiological effect on alive organisms. Not all the representatives of the globe’s flora contain these unique substances. Alkaloid cytisine is to be found mainly in the plants of the fabaceous family - Fabaceae. For the cytisine production the seeds of Thermopsis lanceolata R.Br (T. lanceolata R.Br and Cytisus laburnum (C. laburnum are used as a raw material. The object of the research is T. lanceolata cell culture. Sterile sprouts are used at the first stage of the experiment. Callus genesis is accompanied with dedifferentiation. It leads to the cellular organization simplification. Based on an important property of a plant cell, such as totipotency, there appears the formation of the “de novo” biosynthetic device. The cultivation algorithm consists of two basic stages: (i the cultivation conditions optimization of callus with a high level of the primary metabolites biosynthesis (Aspartat – lysine; (ii the research of cultivation chemical and physical factors influence on the secondary metabolite (cytisine biosynthesis and accumulation. During the cultivation the Murashige and Skoog classical recipe of nutrient medium will be used. Optimization of the cultivation conditions will concern the phytohormones, macro- and micronutrients content, as the purpose of optimization is the production of the determined high-level competence embriogenical callus. The main problem is genetic heterogeneity of a cellular population and instability of morpho-physiological processes. The correct management of higher plants cells population is possible at the synchronization of a cellular cycle phases. The references analysis has shown that it is almost impossible to synchronize cellular cycles in the culture of plant tissue. The application of chemical

  15. 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

  16. An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis

    Directory of Open Access Journals (Sweden)

    Hana Doušová

    2015-05-01

    Full Text Available 2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine. However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.

  17. Rhodium-Catalyzed Denitrogenative [3+2] Cycloaddition: Access to Functionalized Hydroindolones and the Framework of Montanine-Type Amaryllidaceae Alkaloids.

    Science.gov (United States)

    Yang, Hongjian; Hou, Shengtai; Tao, Cheng; Liu, Zhao; Wang, Chao; Cheng, Bin; Li, Yun; Zhai, Hongbin

    2017-09-18

    Rhodium-catalyzed denitrogenative [3+2] cycloaddition of 1-sulfonyl-1,2,3-triazoles with cyclic silyl dienol ethers has been developed for the synthesis of functionalized hydroindolones or their corresponding silyl ethers. The present method has been employed to construct synthetically valuable bicyclo[3.3.1]alkenone derivatives and pyrrolidine-ring-containing bicyclic indole compounds. As a further synthetic application, a stereoselective synthesis of 5,11-methanomorphanthridin-3-one, which shares a key skeleton with montanine-type Amaryllidaceae alkaloids has been achieved by using this chemistry. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  18. [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.

  19. 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

  20. 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.

  1. 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.

  2. 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.

  3. 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.

  4. 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)

  5. 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

  6. Conformational study of cinchona and ephedra alkaloids

    NARCIS (Netherlands)

    Dijkstra, Gerard Durk Henk

    1991-01-01

    Chirality and Natun an closely associated. Living organisms use chiral catalysts (enzymes) to synthesize many of their chemical constituents. Over millions of years the complex compositions of enzymes have developed into efficient and specific catalysts for the synthesis (and breakdown) of chiral

  7. 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.

  8. 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.

  9. 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.

  10. 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.

  11. 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.

  12. 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.

  13. 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.

  14. 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.

  15. 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)

  16. Alkaloids and Phenolic Compounds from Sida rhombifolia L. (Malvaceae) and Vasorelaxant Activity of Two Indoquinoline Alkaloids.

    Science.gov (United States)

    Chaves, Otemberg Souza; Teles, Yanna Carolina Ferreira; Monteiro, Matheus Morais de Oliveira; Mendes Junior, Leônidas das Graças; Agra, Maria de Fátima; Braga, Valdir de Andrade; Silva, Tânia Maria Sarmento; Souza, Maria de Fátima Vanderlei de

    2017-01-06

    The follow-up of phytochemical and pharmacological studies of Sida rhombifolia L. (Malvaceae) aims to strengthen the chemosystematics and pharmacology of Sida genera and support the ethnopharmacological use of this species as hypotensive herb. The present work reports phytoconstituents isolated and identified from aerial parts of S. rhombifolia by using chromatographic and spectroscopic methods. The study led to the isolation of scopoletin ( 1 ), scoporone ( 2 ), ethoxy-ferulate ( 3 ), kaempferol ( 4 ), kaempferol-3- O -β-d-glycosyl-6''-α-d-rhamnose ( 5 ), quindolinone ( 6 ), 11-methoxy-quindoline ( 7 ), quindoline ( 8 ), and the cryptolepine salt ( 9 ). The alkaloids quindolinone ( 6 ) and cryptolepine salt ( 9 ) showed vasorelaxant activity in rodent isolated mesenteric arteries.

  17. Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.

    Science.gov (United States)

    Antropow, Alyssa H; Garcia, Nicholas R; White, Kolby L; Movassaghi, Mohammad

    2018-06-04

    The first enantioselective total synthesis of (-)-vallesine via a strategy that features a late-stage regioselective C17-oxidation followed by a highly stereoselective transannular cyclization is reported. The versatility of this approach is highlighted by the divergent synthesis of the archetypal alkaloid of this family, (+)-aspidospermidine, and an A-ring-oxygenated derivative, (+)-deacetylaspidospermine, the precursor to (-)-vallesine, from a common intermediate.

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

    Directory of Open Access Journals (Sweden)

    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.

  19. 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

  20. 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.

  1. [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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  6. 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...

  7. 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

  8. 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.

  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. 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...

  11. In vitro anticancer activity and cytotoxicity of some papaver alkaloids ...

    African Journals Online (AJOL)

    Materials and Methods: The Vero and HeLa cell lines were treated with various concentrations (1-300 μg/mL) of alkaloids for 48 h. Values for cytotoxicity measured by MTT assay were expressed as the concentration that causes a 50% decrease in cell viability (IC50) (μg/mL). Results: Berberine and macranthine were the ...

  12. 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.

  13. 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.

  14. 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 ...

  15. 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).

  16. 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.

  17. 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

  18. 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.

  19. 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...

  20. 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.

  1. 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.

  2. Pyrrolizidine alkaloids in food: A spectrum of potential health consequences

    Science.gov (United States)

    Contamination of grain with 1,2-dehydropyrrolizidine ester alkaloids (dehydroPAs) and their N-oxides is responsible for large incidents of acute and subacute food poisoning, with high morbidity and mortality, in Africa and in central and south Asia. Herbal medicines and teas containing dehydroPAs ha...

  3. 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

  4. 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...

  5. 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

  6. 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.

  7. Effect Of CARICAPRYL-99 Seed Alkaloid Extract On The Serum ...

    African Journals Online (AJOL)

    Summary: Activity of alkaloid extract of caricapryl–99 seeds (Carica papaya Linn seeds) on the serum levels of steroid hormones was studied in adult male albino rats. Three tolerated doses obtained from the graph of percectage toxicity (10, 50 and 150 mg/kg) were separately administered orally, daily for three days to ...

  8. 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

  9. [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

  10. 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

  11. 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)

  12. Pyrrolizidine alkaloid-derived DNA adducts are common toxicological biomarkers of pyrrolizidine alkaloid N-oxides.

    Science.gov (United States)

    He, Xiaobo; Xia, Qingsu; Woodling, Kellie; Lin, Ge; Fu, Peter P

    2017-10-01

    There are 660 pyrrolizidine alkaloids (PAs) and PA N-oxides present in the plants, with approximately half being possible carcinogens. We previously reported that a set of four PA-derived DNA adducts is formed in the liver of rats administered a series of hepatocarcinogenic PAs and a PA N-oxide. Based on our findings, we hypothesized that this set of DNA adducts is a common biological biomarker of PA-induced liver tumor formation. In this study, we determined that rat liver microsomal metabolism of five hepatocarcinogenic PAs (lasiocarpine, retrorsine, riddelliine, monocrotaline, and heliotrine) and their corresponding PA N-oxides produced the same set of DNA adducts. Among these compounds, lasiocarpine N-oxide, retrorsine N-oxide, monocrotaline N-oxide, and heliotrine N-oxide are for first time shown to be able to produce these DNA adducts. These results further support the role of these DNA adducts as potential common biomarkers of PA-induced liver tumor initiation. Copyright © 2017. Published by Elsevier B.V.

  13. Pyrrolizidine alkaloid-derived DNA adducts are common toxicological biomarkers of pyrrolizidine alkaloid N-oxides

    Directory of Open Access Journals (Sweden)

    Xiaobo He

    2017-10-01

    Full Text Available There are 660 pyrrolizidine alkaloids (PAs and PA N-oxides present in the plants, with approximately half being possible carcinogens. We previously reported that a set of four PA-derived DNA adducts is formed in the liver of rats administered a series of hepatocarcinogenic PAs and a PA N-oxide. Based on our findings, we hypothesized that this set of DNA adducts is a common biological biomarker of PA-induced liver tumor formation. In this study, we determined that rat liver microsomal metabolism of five hepatocarcinogenic PAs (lasiocarpine, retrorsine, riddelliine, monocrotaline, and heliotrine and their corresponding PA N-oxides produced the same set of DNA adducts. Among these compounds, lasiocarpine N-oxide, retrorsine N-oxide, monocrotaline N-oxide, and heliotrine N-oxide are for first time shown to be able to produce these DNA adducts. These results further support the role of these DNA adducts as potential common biomarkers of PA-induced liver tumor initiation.

  14. 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.

  15. The First Total Synthesis of Dragmacidin D

    OpenAIRE

    Garg, Neil K.; Sarpong, Richmond; Stoltz, Brian M.

    2002-01-01

    The first total synthesis of the biologically significant bis-indole alkaloid dragmacidin D (5) has been achieved. Thermal and electronic modulation provides the key for a series of palladium-catalyzed Suzuki cross-coupling reactions that furnished the core structure of the complex guanidine- and aminoimidazole-containing dragmacidins. Following this crucial sequence, a succession of meticulously controlled final events was developed leading to the completion of the natural product.

  16. 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.

  17. 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.

  18. 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.

  19. 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.

  20. 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.

  1. A brief review on synthesis & applications of β-enamino carbonyl compounds

    Directory of Open Access Journals (Sweden)

    yellajyosula L N Murthy

    2012-01-01

    Full Text Available Owing to the wide range applications of β-enamino esters (enamines of β–dicarbonyl compounds in pharmaceuticals and as building blocks for the synthesis of a variety of heterocyclic compounds, β-amino esters, β-amino acids, γ-amino alcohols, peptides and alkaloids a number of methods have been developed so far for the synthesis of these compounds. Due to the importance of these compounds as intermediates in organic synthesis, a concised review is presented.

  2. Studies on preparation of some alkaloid complexes and solvent extraction

    Energy Technology Data Exchange (ETDEWEB)

    Mohamed, A A

    1990-12-31

    Describes the various methods available in the literature for the determination of different classes of alkaloids spectrochemical (e.g.spectrophotometry and colorimetry, fluorimetry and phosphorimetry, nephelometry and reiractometry), electrochemical (e.g. polarography, amperometry, conductometry, coulometry and potentiometry), volumetric (e.q. acid-base, iodometry , bromimetry , oxidimetry, complexometry and precipitation ) and miscellaneous methods (e.g.gasliquid chromatography, gravimetry, thermometry and rediometry ) has been discussed. 31 tabs; 29 figs; 402 refs.

  3. Studies on preparation of some alkaloid complexes and solvent extraction

    International Nuclear Information System (INIS)

    Mohamed, A.A.

    1989-01-01

    Describes the various methods available in the literature for the determination of different classes of alkaloids spectrochemical (e.g.spectrophotometry and colorimetry, fluorimetry and phosphorimetry, nephelometry and reiractometry), electrochemical (e.g. polarography, amperometry, conductometry, coulometry and potentiometry), volumetric (e.q. acid-base, iodometry , bromimetry , oxidimetry, complexometry and precipitation ) and miscellaneous methods (e.g.gasliquid chromatography, gravimetry, thermometry and rediometry ) has been discussed

  4. Coumarins and alkaloids in shoot culture of Ruta graveolens L.

    Directory of Open Access Journals (Sweden)

    Halina Ekiert

    2014-01-01

    Full Text Available A shoot culture of Ruta graveolens L. (Rutaceae was maintained in the stationary liquid phase. From the cultured shoots seven compounds were isolated and identified as psoralen, bergapten, xanthotoxin, isopimpinellin (linear furanocoumarins, rutamarin (linear dihydrofuranocoumarin, kokusaginine and skimmianine (furanoquinoline alkaloids by spectral methods. The compounds are known as secondary metabolites of the intact plant, as well as its cell and tissue cultures.

  5. Anxiolytic-like effects of erythrinian alkaloids from Erythrina suberosa

    Energy Technology Data Exchange (ETDEWEB)

    Serrano, Maria Amelia R.; Batista, Andrea N. de L.; Bolzani, Vanderlan da S.; Santos, Luciana de A. [UNESP, Araraquara, SP (Brazil). Inst. de Quimica; Nogueira, Paulo J. de C.; Nunes-de-Souza, Ricardo L. [UNESP, Araraquara, SP (Brazil). Faculdade de Ciencias Farmaceuticas; Latif, Abdul; Arfan, Mohammad [University of Peshawar, Peshawar (Pakistan). Inst. of Chemical Sciences

    2011-07-01

    Two alkaloids, erysodine (1) and erysothrine (2) were isolated from the flowers of a Pakistani medicinal plant, Erythrina suberosa. These compounds were investigated for anxiolytic properties, and the results showed significant effect, in an acute oral treatment with 1-2, which were suspended in saline (NaCl 0.9%) plus DMSO 1%, and evaluated in 122 Swiss male mice exposed to two tests of anxiety - the elevated plus-maze (EPM) and the light/dark transition model (LDTM). (author)

  6. Anxiolytic-like effects of erythrinian alkaloids from Erythrina suberosa

    International Nuclear Information System (INIS)

    Serrano, Maria Amelia R.; Batista, Andrea N. de L.; Bolzani, Vanderlan da S.; Santos, Luciana de A.; Nogueira, Paulo J. de C.; Nunes-de-Souza, Ricardo L.; Latif, Abdul; Arfan, Mohammad

    2011-01-01

    Two alkaloids, erysodine (1) and erysothrine (2) were isolated from the flowers of a Pakistani medicinal plant, Erythrina suberosa. These compounds were investigated for anxiolytic properties, and the results showed significant effect, in an acute oral treatment with 1-2, which were suspended in saline (NaCl 0.9%) plus DMSO 1%, and evaluated in 122 Swiss male mice exposed to two tests of anxiety - the elevated plus-maze (EPM) and the light/dark transition model (LDTM). (author)

  7. [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.

  8. Tetracyclic indole alkaloids with antinematode activity from Uncaria rhynchophylla.

    Science.gov (United States)

    Kong, Fandong; Ma, Qingyun; Huang, Shengzhuo; Yang, Shuang; Fu, Linran; Zhou, Liman; Dai, Haofu; Yu, Zhifang; Zhao, Youxing

    2017-06-01

    A new tetracyclic indole alkaloid, 17-O-methyl-3,4,5,6-tetradehydrogeissoschizine, together with seven known ones, were isolated from the aerial part of Uncaria rhynchophylla. Their structures were unambiguously elucidated by spectroscopic methods and comparing with the literature data. Among them, compounds 1, 3, 4 and 6-8 showed potent to moderate antinematode activities against Panagrellus redivevus at a concentration of 250 μg/mL.

  9. Pyrrolizidine Alkaloids: Chemistry, Pharmacology, Toxicology and Food Safety.

    Science.gov (United States)

    Moreira, Rute; Pereira, David M; Valentão, Patrícia; Andrade, Paula B

    2018-06-05

    Pyrrolizidine alkaloids (PA) are widely distributed in plants throughout the world, frequently in species relevant for human consumption. Apart from the toxicity that these molecules can cause in humans and livestock, PA are also known for their wide range of pharmacological properties, which can be exploited in drug discovery programs. In this work we review the current body of knowledge regarding the chemistry, toxicology, pharmacology and food safety of PA.

  10. Acetylcholinesterase inhibitory activity of pyrrolizidine alkaloids from Echium confusum Coincy.

    Science.gov (United States)

    Benamar, Houari; Tomassini, Lamberto; Venditti, Alessandro; Marouf, Abderrazak; Bennaceur, Malika; Serafini, Mauro; Nicoletti, Marcello

    2017-06-01

    Four pyrrolizidine alkaloids, namely 7-O-angeloyllycopsamine N-oxide 1, echimidine N-oxide 2, echimidine 3 and 7-O-angeloylretronecine 4, were isolated for the first time from the whole plant ethanolic extract of Echium confusum Coincy, through bioassay-guided approach. Their structures were determined by spectroscopic means. All the isolates compounds showed moderate activities in inhibiting AChE, with IC50 0.276-0.769.

  11. 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.

  12. 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.

  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. 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

  15. A Simplified Procedure for Indole Alkaloid Extraction from Catharanthus roseus Combined with a Semi-synthetic Production Process for Vinblastine

    Directory of Open Access Journals (Sweden)

    Marja-Liisa Riekkola

    2007-07-01

    Full Text Available Dried leaves of Catharanthus roseus were extracted with aqueous acidic 0.1 M solution of HCl. Alkaloid-embonate complexes were obtained as precipitates by treating the extract with an alkaline (NaOH solution of embonic acid (4,4-methylene-bis-3-hydroxynaphtalenecarboxylic acid. The precipitate mainly consisted of catharanthine and vindoline embonates and it was directly used as the starting material for a semi-synthesis of the anti-cancer bisindole alkaloid vinblastine. The coupling reaction involved oxidation of catharanthine in aqueous acidic medium by singlet oxygen (1O2, continuously produced in situ by the reaction between H2O2 with NaClO. An excess of NaBH4 was used for the reduction step. Analysis of the reaction mixture indicated a maximum yield of 20% for vinblastine at pH 8.3, based on the initial amount of catharanthine concentration. Direct-injection electrospray ionization mass spectrometry in positive ion mode was used for the identification of vinblastine. The mass spectra of vinblastine were dominated by the corresponding protonated molecular ion [M+H]+ at m/z 811 and the characteristic fragment ions matched with those of the standard compound.

  16. Monitoring changes in anthocyanin and steroid alkaloid glycoside content in lines of transgenic potato plants using liquid chromatography/mass spectrometry.

    Science.gov (United States)

    Stobiecki, Maciej; Matysiak-Kata, Iwona; Frański, Rafał; Skała, Jacek; Szopa, Jan

    2003-03-01

    Transgenic potato plants overexpressing and repressing enzymes of flavonoids biosynthesis were created and analyzed. The selected plants clearly showed the expected changes in anthocyanins synthesis level. Overexpression of a DNA encoding dihydroflavonol 4-reductase (DFR) in sense orientation resulted in an increase in tuber anthocyanins, a 4-fold increase in petunidin and pelargonidin derivatives. A significant decrease in anthocyanin level was observed when the plant was transformed with a corresponding antisense construct. The transformation of potato plants was also accompanied by significant changes in steroid alkaloid glycosides (SAG) level in transgenic potato tuber. The changes in SAGs content was not dependent on flavonoid composition in transgenic potato. However, in an extreme situation where the highest (DFR11) or the lowest (DFRa3) anthocyanin level was detected the positive correlation with steroid alkaloid content was clearly visible. It is suggested that the changes in SAGs content resulted from chromatin stressed upon transformation. A liquid chromatography/mass spectrometry (LC/MS) system with electrospray ionization was applied for profiling qualitative and quantitative changes of steroid alkaloid glycosides in tubers of twelve lines of transgenic potato plants. Except alpha-chaconine and alpha-solanine, in the extracts from dried tuber skin alpha-solamargine and alpha-solasonine, triglycosides of solasonine, were identified in minor amounts, triglycosides of solanidine dehydrodimers were also recognized.

  17. CO2 as a C1-organic building block: Enantioselective electrocarboxylation of aromatic ketones with CO2catalyzed by cinchona alkaloids under mild conditions

    International Nuclear Information System (INIS)

    Chen, Bao-Li; Tu, Zhuo-Ying; Zhu, Hong-Wei; Sun, Wen-Wen; Wang, Huan; Lu, Jia-Xing

    2014-01-01

    Highlights: •Cinchona alkaloids catalysis achieve enantioselective electrocarboxylation of racemic aromatic ketones. •The applications of CO 2 enantioselective electrochemical fixation into optically active hydroxyl carboxylic acids have been expanded. •The applications of alkaloids have been expanded. •The applications of asymmetric synthesis by electrochemical methodology have been expanded. -- Abstract: The enantioselective electrocarboxylation of pro-chiral aromatic ketones (2-acetonaphthone, 1-(6-methoxy-2-naphthyl)ethanone, 1-(4-methoxy-1-naphthyl)ethanone) with atmospheric pressure of CO 2 catalyzed by cinchona alkaloids in the presence of phenol was investigated in an undivided cell for the first time to give optically active 2-hydroxy-2-arylpropionic acid. For the model compound 2-acetonaphthone, the influence of various reaction conditions, such as cathode material, current density, catalyst type, ratio of proton to catalyst and catalyst quantity, on the enantiomeric excesses (ee) and yield has been investigated. Under the optimized conditions of 2-acetonaphthone, all the aromatic ketones examined are converted into corresponding optically active 2-hydroxy-2-arylpropionic acids in moderate yield (32.2% - 41.3%) and ee (48.1% - 48.6%). In addition, the electrochemical behavior of 2-acetonaphthone has been studied by cyclic voltammetry (CV) in the absence and presence of CO 2 . Moreover, the probable reaction pathway was proposed accordingly

  18. 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.

  19. 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.

  20. [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.

  1. 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...

  2. 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,...

  3. 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...

  4. 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)

  5. 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.

  6. 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

  7. 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.

  8. 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...

  9. 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...

  10. 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...

  11. [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.

  12. 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.

  13. 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

  14. [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.

  15. 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...

  16. 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),

  17. 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.

  18. Tyrosine aminotransferase contributes to benzylisoquinoline alkaloid biosynthesis in opium poppy.

    Science.gov (United States)

    Lee, Eun-Jeong; Facchini, Peter J

    2011-11-01

    Tyrosine aminotransferase (TyrAT) catalyzes the transamination of L-Tyr and α-ketoglutarate, yielding 4-hydroxyphenylpyruvic acid and L-glutamate. The decarboxylation product of 4-hydroxyphenylpyruvic acid, 4-hydroxyphenylacetaldehyde, is a precursor to a large and diverse group of natural products known collectively as benzylisoquinoline alkaloids (BIAs). We have isolated and characterized a TyrAT cDNA from opium poppy (Papaver somniferum), which remains the only commercial source for several pharmaceutical BIAs, including codeine, morphine, and noscapine. TyrAT belongs to group I pyridoxal 5'-phosphate (PLP)-dependent enzymes wherein Schiff base formation occurs between PLP and a specific Lys residue. The amino acid sequence of TyrAT showed considerable homology to other putative plant TyrATs, although few of these have been functionally characterized. Purified, recombinant TyrAT displayed a molecular mass of approximately 46 kD and a substrate preference for L-Tyr and α-ketoglutarate, with apparent K(m) values of 1.82 and 0.35 mm, respectively. No specific requirement for PLP was detected in vitro. Liquid chromatography-tandem mass spectrometry confirmed the conversion of L-Tyr to 4-hydroxyphenylpyruvate. TyrAT gene transcripts were most abundant in roots and stems of mature opium poppy plants. Virus-induced gene silencing was used to evaluate the contribution of TyrAT to BIA metabolism in opium poppy. TyrAT transcript levels were reduced by at least 80% in silenced plants compared with controls and showed a moderate reduction in total alkaloid content. The modest correlation between transcript levels and BIA accumulation in opium poppy supports a role for TyrAT in the generation of alkaloid precursors, but it also suggests the occurrence of other sources for 4-hydroxyphenylacetaldehyde.

  19. 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...

  20. Bromopyrrole alkaloids from the Caribbean sponge Agelas cerebrum

    International Nuclear Information System (INIS)

    Regalado, Erik L.; Laguna, Abilio; Mendiola, Judith; Thomas, Olivier P.; Nogueiras, Clara

    2011-01-01

    Bioguided fractionation of Agelas cerebrum crude extract resulted in isolation of four bromopyrrole and four bromopyrrole aminoimidazole alkaloids, identified as 5-bromopyrrole-2-carboxylic acid (1), 4-bromopyrrole-2-carboxylic acid (2), 3,4-bromopyrrole-2-carboxylic acid (3), 4,5-bromopyrrole-2-carboxylic acid (4), oroidin (5), bromoageliferin (6), dibromoageliferin (7) and dibromosceptrin (8) on the basis of spectroscopic data analyses (UV, IR, HRMS, 1D and 2D NMR) and comparison with literature data. This is the first report of compounds 2 and 3 in a marine sponge belonging to the Agelas genus and the first evidence of the presence of 1 from a natural source. (author)

  1. An azafluorenone alkaloid and a megastigmane from Unonopsis lindmanii (Annonaceae)

    International Nuclear Information System (INIS)

    Yoshida, Nidia C.; Siqueira, Joao M. de; Rodrigues, Ricardo P.; Correia, Rodolfo P.; Garcez, Walmir S.

    2013-01-01

    The azafluorenone alkaloid 5,8-dimethoxy-7-hydroxy-1-methyl-4-azafluoren-9-one and the megastigman (–)-(5R*, 6S*)-megastigman-3-one-10,7-olide were isolated from aerial parts of Unonopsis lindmanii (Annonaceae), along with the known compounds (3S*,5S*,8R*)-3,5-dihydroxymegastigma-6,7-dien-9-one (grasshopper ketone), N-trans-feruloyltyramine, (–)-anonaine, (–)-asimilobine, liriodenine and (–)-syringaresinol. This is the first description of the presence of megastigmanes in Annonaceae. The structures of the compounds were elucidated based on spectroscopic data. (author)

  2. Two new similar alkaloids from Portulaca oleracea L.

    Science.gov (United States)

    Li, Cuiyu; Ying, Zheming; Gao, Mingzhe; Wei, Wenjuan; Hao, Dong; Xu, Liang; Tao, Xiaojun; Zhang, Wenjie; Ying, Xixiang; Liu, Jing

    2017-08-01

    Two novel alkaloids named oleraciamide A (1) and oleraciamide B (2) were isolated from Portulaca oleracea L., and spectroscopic methods including 1D and 2D nuclear magnetic resonance and high-resolution electrospray ionisation quadrupole-time of flight mass spectrometer spectrometry techniques are employed to determine their structures. Oleraciamide A (1) was evaluated no cytotoxicity at concentrations up to 80 μM over 72 h against human adipose-derived stem cells (hADSCs) by CCK-8 method.

  3. Isopalhinine A, a unique pentacyclic Lycopodium alkaloid from Palhinhaea cernua.

    Science.gov (United States)

    Dong, Liao-Bin; Gao, Xiu; Liu, Fei; He, Juan; Wu, Xing-De; Li, Yan; Zhao, Qin-Shi

    2013-07-19

    A new pentacyclic (5/6/6/6/7) Lycopodium alkaloid named isopalhinine A (1), which possesses a sterically congested architecture built with a tricyclo[4.3.1.0(3,7)]decane (isotwistane) moiety and a 1-azabicyclo[4.3.1]decane moiety, and palhinines B (2) and C (3) were isolated from Palhinhaea cernua. The structure and absolute configuration of 1 were elucidated by a combination of NMR spectra, optical rotation calculation, and X-ray diffraction experiment. A possible biogenetic pathway was also proposed.

  4. Aedes aegypti Larvicidal Sesquiterpene Alkaloids from Maytenus oblongata.

    Science.gov (United States)

    Touré, Seindé; Nirma, Charlotte; Falkowski, Michael; Dusfour, Isabelle; Boulogne, Isabelle; Jahn-Oyac, Arnaud; Coke, Maïra; Azam, Didier; Girod, Romain; Moriou, Céline; Odonne, Guillaume; Stien, Didier; Houël, Emeline; Eparvier, Véronique

    2017-02-24

    Four new sesquiterpene alkaloids (1-4) with a β-dihydroagrofuran skeleton and a new triterpenoid (5) were isolated from an ethyl acetate extract of Maytenus oblongata stems. Their structures were elucidated using 1D and 2D NMR spectroscopy as well as MS and ECD experiments. The M. oblongata stem EtOAc extract and the pure compounds isolated were tested for larvicidal activity against Aedes aegypti under laboratory conditions, and compounds 2 and 3 were found to be active.

  5. An azafluorenone alkaloid and a megastigmane from Unonopsis lindmanii (Annonaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Yoshida, Nidia C., E-mail: nidiayoshida@usp.br [Universidade de Sao Paulo (USP), SP (Brazil). Instituto de Quimica; Siqueira, Joao M. de [Universidade Federal de Sao Joao Del Rei, Divinpolis, MG (Brazil). Departamento de Farmacia; Rodrigues, Ricardo P. [Universidade de Sao Paulo (USP), Ribeirao Preto, SP (Brazil). Faculdade de Ciencias Farmaceuticas; Correia, Rodolfo P. [Universidade de Sao Paulo (USP), SP (Brazil). Instituto de Ciencias Biomedicas; Garcez, Walmir S., E-mail: walmir.garcez@ufms.br [Universidade Federal de Mato Grosso do Sul (UFMS), Campo Grande, MS (Brazil). Departamento de Quimica

    2013-04-15

    The azafluorenone alkaloid 5,8-dimethoxy-7-hydroxy-1-methyl-4-azafluoren-9-one and the megastigman (-)-(5R*, 6S*)-megastigman-3-one-10,7-olide were isolated from aerial parts of Unonopsis lindmanii (Annonaceae), along with the known compounds (3S*,5S*,8R*)-3,5-dihydroxymegastigma-6,7-dien-9-one (grasshopper ketone), N-trans-feruloyltyramine, (-)-anonaine, (-)-asimilobine, liriodenine and (-)-syringaresinol. This is the first description of the presence of megastigmanes in Annonaceae. The structures of the compounds were elucidated based on spectroscopic data. (author)

  6. Bromopyrrole alkaloids from the Caribbean sponge Agelas cerebrum

    Energy Technology Data Exchange (ETDEWEB)

    Regalado, Erik L.; Laguna, Abilio, E-mail: erikluis18@gmail.co [Center of Marine Bioproducts, Havana (Cuba). Dept. of Chemistry; Mendiola, Judith [Institute of Tropical Medicine Pedro Kouri (IPK), Havana (Cuba). Dept. of Parasitology; Thomas, Olivier P. [Universite de Nice-Sophia Antipolis (France). Lab. de Chimie des Molecules Bioactives et des Aromes; Nogueiras, Clara [University of Havana, San Lazaro y L, Havana (Cuba). Faculty of Chemistry. Center of Natural Products

    2011-07-01

    Bioguided fractionation of Agelas cerebrum crude extract resulted in isolation of four bromopyrrole and four bromopyrrole aminoimidazole alkaloids, identified as 5-bromopyrrole-2-carboxylic acid (1), 4-bromopyrrole-2-carboxylic acid (2), 3,4-bromopyrrole-2-carboxylic acid (3), 4,5-bromopyrrole-2-carboxylic acid (4), oroidin (5), bromoageliferin (6), dibromoageliferin (7) and dibromosceptrin (8) on the basis of spectroscopic data analyses (UV, IR, HRMS, 1D and 2D NMR) and comparison with literature data. This is the first report of compounds 2 and 3 in a marine sponge belonging to the Agelas genus and the first evidence of the presence of 1 from a natural source. (author)

  7. A Novel Antimicrobial Phenanthrene Alkaloid from Bryopyllum pinnatum

    Directory of Open Access Journals (Sweden)

    Donatus Ebere Okwu

    2011-01-01

    Full Text Available Phenenthrene alkaloid identified as 1-ethanamino 7 hex-1-yne-5I-one phenanthrene was isolated from the ethanolic extract of the leaves of Bryophyllum pinnatum (syn. B. calcinum kalanchoe pinnata a versatile Nigeria medicinal plant. The structure was elucidated using NMR, IR, UV and MS spectral data. Antimicrobial studies showed that the isolated compound successfully inhibited Psuedomonas aeruginosa, Klebsiella pneumonia, Staphylococcus aureus, Escherichia coli, Candida albicans and Aspergillus niger. This result authenticates the use of bryophyllum pinantum in phytomedicine for disease prevention and treatment of infections.

  8. Immunoassay approach for diagnosis of exposure to pyrrolizidine alkaloids.

    Science.gov (United States)

    Li, Na; Zhang, Fan; Lian, Wei; Wang, Huali; Zheng, Jiang; Lin, Ge

    2017-07-03

    Numerous pyrrolizidine alkaloid (PA) poisoning cases have been documented worldwide. Protein covalent binding with reactive metabolites generated from metabolic activation of PAs to form pyrrole-protein adducts is suggested to be a primary mechanism of PA-induced toxicities. The present study aimed to develop antibodies for diagnosis of PA exposure. Polyclonal antibodies were raised in rabbits and proven to specifically recognize pyrrole-protein adducts regardless of amino acid residues modified by the reactive metabolites of PAs. The developed antibodies were successfully applied to detect pyrrole-protein adducts in blood samples obtained from PA-treated rats and exhibited a potential for the clinical diagnosis of PA exposure.

  9. Structure, Biosynthesis, and Occurrence of Bacterial Pyrrolizidine Alkaloids.

    Science.gov (United States)

    Schimming, Olivia; Challinor, Victoria L; Tobias, Nicholas J; Adihou, Hélène; Grün, Peter; Pöschel, Laura; Richter, Christian; Schwalbe, Harald; Bode, Helge B

    2015-10-19

    Pyrrolizidine alkaloids (PAs) are widespread plant natural products with potent toxicity and bioactivity. Herein, the identification of bacterial PAs from entomopathogenic bacteria using differential analysis by 2D NMR spectroscopy (DANS) and mass spectrometry is described. Their biosynthesis was elucidated to involve a non-ribosomal peptide synthetase. The occurrence of these biosynthesis gene clusters in Gram-negative and Gram-positive bacteria indicates an important biological function in bacteria. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Curare Alkaloids: Constituents of a Matis Dart Poison.

    Science.gov (United States)

    Malca Garcia, Gonzalo R; Hennig, Lothar; Shelukhina, Irina V; Kudryavtsev, Denis S; Bussmann, Rainer W; Tsetlin, Victor I; Giannis, Athanassios

    2015-11-25

    A phytochemical study of dart and arrow poison from the Matis tribe led to the identification of D-(-)-quinic acid, L-malic acid, ethyldimethylamine, magnoflorine, and five new bisbenzyltetrahydroisoquinoline alkaloids (BBIQAs), 1-5. D-Tubocurarine could not be identified among these products. BBIQA (3) contains a unique linkage at C-8 and C-11'. All structures were characterized by a combination of NMR and HRESIMS data. The effects of Matis poison and individual BBIQAs (1-3) on rat muscle nAChR expressed in Xenopus oocytes have been investigated using the two-electrode voltage clamp technique.

  11. Parallel Synthesis and Biocatalytic Amplification of Marine-Inspired Libraries: An Integrated Approach Toward Discovering New Chemotherapeutics

    Science.gov (United States)

    2007-09-01

    synthesis and biocatalysis. We will use a combination of highly efficient chemistry and biocatalysis to prepare a library of small organic molecules whose...potential for the synthesis of diverse alkaloids . KEY RESEARCH ACCOMPLISHMENTS OF THIS REPORTING PERIOD Cyclopentenone libraries were screened for...growth and proliferation of cancer cells. The newer approach is to use the tools of chemical synthesis to create large collections (“libraries”)

  12. Modulatory Effects of Eschscholzia californica Alkaloids on Recombinant GABAA Receptors

    Directory of Open Access Journals (Sweden)

    Milan Fedurco

    2015-01-01

    Full Text Available The California poppy (Eschscholzia californica Cham. contains a variety of natural compounds including several alkaloids found exclusively in this plant. Because of the sedative, anxiolytic, and analgesic effects, this herb is currently sold in pharmacies in many countries. However, our understanding of these biological effects at the molecular level is still lacking. Alkaloids detected in E. californica could be hypothesized to act at GABAA receptors, which are widely expressed in the brain mainly at the inhibitory interneurons. Electrophysiological studies on a recombinant α1β2γ2 GABAA receptor showed no effect of N-methyllaurotetanine at concentrations lower than 30 μM. However, (S-reticuline behaved as positive allosteric modulator at the α3, α5, and α6 isoforms of GABAA receptors. The depressant properties of aerial parts of E. californica are assigned to chloride-current modulation by (S-reticuline at the α3β2γ2 and α5β2γ2 GABAA receptors. Interestingly, α1, α3, and α5 were not significantly affected by (R-reticuline, 1,2-tetrahydroreticuline, codeine, and morphine—suspected (S-reticuline metabolites in the rodent brain.

  13. Antioxidative properties of harmane and beta-carboline alkaloids.

    Science.gov (United States)

    Tse, S Y; Mak, I T; Dickens, B F

    1991-07-15

    beta-Carboline alkaloids are derived as a result of condensation between indoleamine (e.g. tryptamine) and short-chain carboxylic acid (e.g. pyruvic acid) or aldehyde (e.g. acetaldehyde), a reaction that occurs readily at room temperature. These compounds have been found endogenously in human and animal tissues and may be formed as a byproduct of secondary metabolism: their endogenous functions however, are not well understood. Indoles and tryptophan derivatives exhibit antioxidative actions by scavenging free radicals and forming resonance stabilized indolyl radicals. Harmane and related compounds exhibited concentration-dependent inhibition of lipid peroxidation (measured as thiobarbiturate reactive products) in a hepatic microsomal preparation incubated with either enzymatic dependent (Fe3+ ADP/NADPH) or non-enzymatic dependent (Fe3+ ADP/dihydroxyfumarate) oxygen radical producing systems. Alkaloids with hydroxyl substitution and a partially desaturated pyridyl ring were found to have the highest antioxidative potencies. Substitution of a hydroxyl group by a methoxyl group at the 6-position resulted in a decrease of greater than 10-fold in the antioxidative activities. Harmane showed high efficacy in an enzymatic system but low efficacy in a non-enzymatic system. The antioxidative effects of harmane in the former system may be attributed to its ability to inhibit oxidative enzymes in the microsomal system. These results suggest that beta-carbolines may also serve as endogenous antioxidants.

  14. 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.

  15. Pyrrolizidine alkaloids in food and feed on the Belgian market.

    Science.gov (United States)

    Huybrechts, Bart; Callebaut, Alfons

    2015-01-01

    Pyrrolizidine alkaloids (PAs) are widely distributed plant toxins with species dependent hepatotoxic, carcinogenic, genotoxic and pneumotoxic risks. In a recent European Food Safety Authority (EFSA) opinion, only two data sets from one European country were received for honey, while one feed data set was included. No data are available for food or feed samples from the Belgian market. We developed an LC-MS/MS method, which allowed the detection and quantification of 16 PAs in a broad range of matrices in the sub ng g(-1) range. The method was validated in milk, honey and hay and applied to honey, tea (Camellia sinensis), scented tea, herbal tea, milk and feed samples bought on the Belgian market. The results confirmed that tea, scented tea, herbal tea and honey are important food sources of pyrrolizidine alkaloid contamination in Belgium. Furthermore, we detected PAs in 4 of 63 commercial milk samples. A high incidence rate of PAs in lucerne (alfalfa)-based horse feed and in rabbit feed was detected, while bird feed samples were less contaminated. We report for the first time the presence of monocrotaline, intermedine, lycopsamine, heliotrine and echimidine in cat food.

  16. The effects of comfrey derived pyrrolizidine alkaloids on rat liver.

    Science.gov (United States)

    Yeong, M L; Clark, S P; Waring, J M; Wilson, R D; Wakefield, S J

    1991-01-01

    Three groups of young adult rats were fed pyrrolizidine alkaloids derived from Russian comfrey to study the effects of the herb on the liver. Group I animals received a single dose of 200 mg/kg body wt, Group II 100 mg/kg three times a week for 3 weeks and Group III 50 mg/kg three times a week for 3 weeks. All rats showed light and electron-microscopic evidence of liver damage, the severity of which was dose dependent. There was swelling of hepatocytes and hemorrhagic necrosis of perivenular cells. There was a concomitant loss of sinusoidal lining cells with disruption of sinusoidal wall and the sinusoids were filled with cellular debris, hepatocyte organelles and red blood cells. Extravasation of red blood cells was evident. Terminal hepatic venules were narrowed by intimal proliferation, and in Group II and III, reiculin fibres radiated from these vessels. These appearances have been described in veno-occlusive disease due to pyrrolizidine alkaloids from other plant sources such as Senecio and Crotalaria. The safety of comfrey, a widely used herb, in relation to human consumption requires further investigation.

  17. 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

  18. Synthesis and pharmacological evaluation of DHβE analogs as neuronal nicotinic acetylcholine receptor antagonists

    DEFF Research Database (Denmark)

    Jepsen, Tue H.; Jensen, Anders A.; Lund, Mads Henrik

    2014-01-01

    Dihydro-β-erythroidine (DHβE) is a member of the Erythrina family of alkaloids and a potent competitive antagonist of the α4β2-subtype of the nicotinic acetylcholine receptors (nAChRs). Guided by an X-ray structure of DHβE in complex with an ACh binding protein, we detail the design, synthesis...

  19. Cu-Mediated Stille Reactions of Sterically Congested Fragments: Towards the Total Synthesis of Zoanthamine

    DEFF Research Database (Denmark)

    Nielsen, Thomas E.; Le Quement, Sebastian; Juhl, Martin

    2005-01-01

    A study on the Stille reaction of alkenyl iodides and starmanes with structural resemblance to retrosynthetic fragments of a projected total synthesis of the marine alkaloid zoanthamine was carried out. A range of reaction conditions was examined, and a protocol developed by Corey utilizing excess...

  20. 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.

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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)

  6. 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.

  7. 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.

  8. 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.

  9. 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

  10. 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.

  11. 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.

  12. 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.

  13. 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.

  14. Synthesis of Calystegine A(3) from Glucose by the Use of Ring-Closing Metathesis

    DEFF Research Database (Denmark)

    Monrad, Rune Nygaard; Pipper, Charlotte Bressen; Madsen, Robert

    2009-01-01

    A synthesis of the nortropane alkaloid calystegine A(3) is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6-iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine...... affords calystegine A(3). The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product....

  15. An Expeditious Stereoselective Synthesis of (−)-Pinidinone from Ethyl Acetoacetate

    International Nuclear Information System (INIS)

    Damodar, Kongara; Jun, Jong-Gab

    2016-01-01

    An expeditious stereoselective synthesis of a naturally occurring 2,6-disubstituted piperidine alkaloid, (−)-pinidinone, has been accomplished with an overall yield of 31% in total eight steps. The synthesis involves ethyl acetoacetate as the starting material and the stereoselective α-aminoallylation of aldehyde with (S)-tert-butanesulfinamide, allyl bromide, and indium and Grubbs' olefin cross-metathesis as the pivotal steps.

  16. Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine A.

    Science.gov (United States)

    Nash, Aaron; Qi, Xiangbing; Maity, Pradip; Owens, Kyle; Tambar, Uttam K

    2018-04-16

    A novel vinylogous Pictet-Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine A. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  17. Synthesis of monoterpene piperidines from the iridoid glucoside antirrhinoside

    DEFF Research Database (Denmark)

    Franzyk, Henrik; Frederiksen, Signe Maria; Jensen, Søren Rosendal

    1997-01-01

    Synthesis of five novel piperidine monoterpene alkaloids using the iridoid glucoside antirrhinoside as a synthon is described. Two strategies for their preparation were investigated: the first possible pathway involved an intermediate diol from which the piperidine ring was expected to be constru......Synthesis of five novel piperidine monoterpene alkaloids using the iridoid glucoside antirrhinoside as a synthon is described. Two strategies for their preparation were investigated: the first possible pathway involved an intermediate diol from which the piperidine ring was expected...... to be constructed via reaction of its ditosylate with an amine; the second strategy involved a double reductive amination as the key step to the piperidine ring, which proved successful. The stereochemistry of C-5 and C-9 in the obtained piperidine monoterpenes was the same as that reported for alfa...

  18. Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway

    International Nuclear Information System (INIS)

    Habermehl, Daniel; Belka, Claus; Jendrossek, Verena; Kammerer, Bernd; Handrick, René; Eldh, Therese; Gruber, Charlotte; Cordes, Nils; Daniel, Peter T; Plasswilm, Ludwig; Bamberg, Michael

    2006-01-01

    The anticancer drug Ukrain (NSC-631570) which has been specified by the manufacturer as semisynthetic derivative of the Chelidonium majus L. alkaloid chelidonine and the alkylans thiotepa was reported to exert selective cytotoxic effects on human tumour cell lines in vitro. Few clinical trials suggest beneficial effects in the treatment of human cancer. Aim of the present study was to elucidate the importance of apoptosis induction for the antineoplastic activity of Ukrain, to define the molecular mechanism of its cytotoxic effects and to identify its active constituents by mass spectrometry. Apoptosis induction was analysed in a Jurkat T-lymphoma cell model by fluorescence microscopy (chromatin condensation and nuclear fragmentation), flow cytometry (cellular shrinkage, depolarisation of the mitochondrial membrane potential, caspase-activation) and Western blot analysis (caspase-activation). Composition of Ukrain was analysed by mass spectrometry and LC-MS coupling. Ukrain turned out to be a potent inducer of apoptosis. Mechanistic analyses revealed that Ukrain induced depolarisation of the mitochondrial membrane potential and activation of caspases. Lack of caspase-8, expression of cFLIP-L and resistance to death receptor ligand-induced apoptosis failed to inhibit Ukrain-induced apoptosis while lack of FADD caused a delay but not abrogation of Ukrain-induced apoptosis pointing to a death receptor independent signalling pathway. In contrast, the broad spectrum caspase-inhibitor zVAD-fmk blocked Ukrain-induced cell death. Moreover, over-expression of Bcl-2 or Bcl-x L and expression of dominant negative caspase-9 partially reduced Ukrain-induced apoptosis pointing to Bcl-2 controlled mitochondrial signalling events. However, mass spectrometric analysis of Ukrain failed to detect the suggested trimeric chelidonine thiophosphortriamide or putative dimeric or monomeric chelidonine thiophosphortriamide intermediates from chemical synthesis. Instead, the Chelidonium

  19. Identification of a new reactive metabolite of pyrrolizidine alkaloid retrorsine: (3H-pyrrolizin-7-yl)methanol.

    Science.gov (United States)

    Fashe, Muluneh M; Juvonen, Risto O; Petsalo, Aleksanteri; Rahnasto-Rilla, Minna; Auriola, Seppo; Soininen, Pasi; Vepsäläinen, Jouko; Pasanen, Markku

    2014-11-17

    Pyrrolizidine alkaloids (PAs) such as retrorsine are common food contaminants that are known to be bioactivated by cytochrome P450 enzymes to putative hepatotoxic, genotoxic, and carcinogenic metabolites known as dehydropyrrolizidine alkaloids (DHPs). We compared how both electrochemical (EC) and human liver microsomal (HLM) oxidation of retrorsine could produce short-lived intermediate metabolites; we also characterized a toxicologically important metabolite, (3H-pyrrolizin-7-yl)methanol. The EC cell was coupled online or offline to a liquid chromatograph/mass spectrometer (LC/MS), whereas the HLM oxidation was performed in 100 mM potassium phosphate (pH 7.4) in the presence of NADPH at 37 °C. The EC cell oxidation of retrorsine produced 12 metabolites, including dehydroretrorsine (m/z 350, [M + H(+)]), which was degraded to a new reactive metabolite at m/z 136 ([M + H(+)]). The molecular structure of this small metabolite was determined using high-resolution mass spectrometry and NMR spectroscopy followed by chemical synthesis. In addition, we also identified another minor but reactive metabolite at m/z 136, an isomer of (3H-pyrrolizin-7-yl)methanol. Both (3H-pyrrolizin-7-yl)methanol and its minor isomer were also observed after HLM oxidation of retrorsine and other hepatotoxic PAs such as lasiocarpine and senkirkin. In the presence of reduced glutathione (GSH), each isomer formed identical GSH conjugates at m/z 441 and m/z 730 in the negative ESI-MS. Because (3H-pyrrolizine-7-yl)methanol) and its minor isomer subsequently reacted with GSH, it is concluded that (3H-pyrrolizin-7-yl)methanol may be a common toxic metabolite arising from PAs.

  20. [Alkaloids and lignans from stems of Piper betle].

    Science.gov (United States)

    Huang, Xiangzhong; Yin, Yan; Huang, Wenquan; Sun, Kuizong; Cheng, Chunmei; Bai, Lian; Dai, Yun

    2010-09-01

    Alkaloids and lignans from the stems of Piper betle were studied. Compounds were isolated and purified by repeated silica gel, reverse phase silica gel, Sephadex LH-20 column chromatography and preparative thin layer chromatography. The structures were elucidated on the basis of spectral analysis. From the ethyl acetate soluble fractions of the 70% acetone extract, ten compounds were isolated and identified as piperine (1), pellitorine (2), N-isobutyl-2E,4E-dodecadienamide (3), dehydropipernonaline (4), piperdardine (5), piperolein-B (6), guineensine (7), (2E,4E)-N-isobutyl-7-(3',4'-methylenedioxyphenyl)-2,4-heptadienamide (8), syringaresinol-O-beta-D-glucopyranoside (9),pinoresinol (10). All Compounds were isolated from the plant for the first time, and compounds 9 and 10 were isolated firstly from the genus.

  1. Furochinoline alkaloids in plants from Rutaceae family – a review

    Directory of Open Access Journals (Sweden)

    Adamska-Szewczyk Aldona

    2016-04-01

    Full Text Available Over the past five years, phytochemical and pharmacological studies have been conducted on material extracted from members of the Rutaceae family. In such work, new furochinoline-structured alkaloids were isolated from Ruta sp. and Dictamnus sp. Beyond the aforementioned, other substances with promising activity were isolated from the less-known species of Zanthoxylum, Evodia, Lonchocarpus, Myrthopsis and Teclea. Currently used forms of extraction, as well as methods of isolation and detection, allow the obtaining of pure, biologically active compounds. Many of these have antifungal, anti-bacterial and anti-plasmodial properties. Others are still being researched as potential drugs, which, in future, may be used in treating those afflicted with HIV and cancer. This article is designed to give the readers a thorough review of the active natural products from the Rutaceae family.

  2. Vitiquinolone--a quinolone alkaloid from Hibiscus vitifolius Linn.

    Science.gov (United States)

    Ramasamy, D; Saraswathy, A

    2014-02-15

    Phytochemical investigations of the powdered root of Hibiscus vitifolius Linn. (Malvaceae) was extracted successively with n-hexane and chloroform. Analysis of the n-hexane extract by GC-MS led to the identification of twenty-six components by comparison of their mass spectra with GC-MS library data. A novel quinolone alkaloid, vitiquinolone (5) together with eight known compounds viz. β-Amyrin acetate (1), n-octacosanol (2), β-Amyrin (3), stigmasterol (4), xanthyletin (6), alloxanthoxyletin (7), xanthoxyletin (8) and betulinic acid (9) were isolated from chloroform extract by column chromatography over silica gel. The structure of vitiquinolone was established on the basis of spectroscopic methods including UV, IR, 1D, 2D NMR and ESI-MS. The known compounds were identified on the basis of their physical and spectroscopic data as reported in the literature. Copyright © 2013 Elsevier Ltd. All rights reserved.

  3. Two new alkaloids from Portulaca oleracea and their cytotoxic activities.

    Science.gov (United States)

    Tian, Jin-Long; Liang, Xiao; Gao, Pin-Yi; Li, Dan-Qi; Sun, Qian; Li, Ling-Zhi; Song, Shao-Jiang

    2014-01-01

    Two new alkaloids named (3R)-3,5-bis(3-methoxy-4-hydroxyphenyl)-2,3-dihydro-2(1H)-pyridinone (1) and 1,5-dimethyl-6-phenyl-1,2-dihydro-1,2,4-triazin-3(2H)-one (2), together with two known compounds (7'R)-N-feruloyl normetanephrine (3) and N-trans-feruloyl tyramine (4) were isolated from the air-dried aerial parts of Portulaca oleracea L. Their structures and configurations were elucidated by spectroscopic methods including 1D NMR, 2D NMR, and HR-MS techniques. In addition, compounds 1-4 were tested for in vitro cytotoxic activities against human lung (K562 and A549) and breast (MCF-7 and MDA-MB-435) cancer cell lines.

  4. Analytical aspects of diterpene alkaloid poisoning with monkshood.

    Science.gov (United States)

    Colombo, Maria Laura; Bugatti, Carlo; Davanzo, Franca; Persico, Andrea; Ballabio, Cinzia; Restani, Patrizia

    2009-11-01

    A sensitive and specific method for aconitine extraction from biological samples was developed. Aconitine, the main toxic alkaloid from plants belonging to Aconitum species (family Ranunculaceae), was determined in plant material by an external standard method, and by a standard addition calibration method in biological fluids. Described here is one fatal case and five intoxications of accidental aconitine poisoning following the ingestion of aconite mistaken for an edible grass, Aruncus dioicus (Walt.) Fernald, "mountain asparagus", and Cicerbita alpina (L.) Wallroth. The aconitine content in urine was in the range 2.94 microg/mL (dead patient)-0.20 microg/mL (surviving patients), which was almost two to four times higher than that in plasma.

  5. Alkaloids from piper: a review of its phytochemistry and pharmacology.

    Science.gov (United States)

    Gutierrez, Rosa Martha Perez; Gonzalez, Adriana Maria Neira; Hoyo-Vadillo, Carlos

    2013-02-01

    Piper has been used for long timelike condiment and food, but also in traditional medicine around of the world. This work resumes the available and up to date work done on members of the Piperaceae family and their uses for therapeutic purposes. Information on Piper genus was gathered via internet using scientific databases such as Scirus, Google Scholar, CAB-abstracts, MedlinePlus, Pubmed, SciFinder, Scopus and Web of Science. The largeleafed perennial plant Piper is used for its spicy aromatic scent and flavor. It has an important presence in the cuisine of different cultures. Another quality of these plants is their known medicinal properties. It has been used as emollient, antirheumatic, diuretic, stimulant, abortifacient, anti-inflammatory, antibacterial, antifungal and antidermatophytic. A survey of the literature shows that the genus Piper is mainly known for its alkaloids with cytotoxic, chemopreventive, antimetastatic and antitumor properties in several types of cancer. Studies of its alkaloids highlight the existence of various potential leads to develop new anti-cancer agents. Modern pharmacology studies have demonstrated that its crude extracts and active compounds possess wide pharmacological activities, especially asantioxidant, anti-depressive, hepatoprotective, antimicrobial, anti-obesity, neuropharmacological, to treat cognitive disorders, anti-hyperlipidemic, anti-feedant, cardioactive, immuno-enhancing, and anti-inflamatory. All this evidence supporting its traditional uses. This review summarizes the up-to-date and comprehensive information concerning the botany, traditional use, phytochemistry and pharmacology of Piper together with its toxicology, and discusses the possible trend and scope for further research on Piper in the future.

  6. Potent New Small-Molecule Inhibitor of Botulinum Neurotoxin Serotype A Endopeptidase Developed by Synthesis-Based Computer-Aided Molecular Design

    Science.gov (United States)

    2009-11-01

    simulations; (4) synthesis and evaluation of the molecules from Step 2 or 3 (e.g., synthesizing and testing AHP). From synthetic chemistry point of view...2000) Synthesis of 6H-indolo [2,3-b][1,6]naphthyridines and related compounds as the 5-Aza analogues of ellipticine alkaloids . J Org Chem 65: 7977–7983...Potent New Small-Molecule Inhibitor of Botulinum Neurotoxin Serotype A Endopeptidase Developed by Synthesis -Based Computer-Aided Molecular Design

  7. 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.

  8. 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

  9. 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.

  10. A survey of plants in Gujarat, India, for alkaloids, saponins, and tannins

    Science.gov (United States)

    Basalingappa L. Hungund; Chandravadan H. Pathak; Chandravadan H. Pathak

    1971-01-01

    A floristic and phytochemical survey of forests in Gujarat State, India, is being undertaken to identify sources of alkaloids, saponins, and tannins. This note is a report on the results of screening 105 plant species collected from that region.

  11. Alkaloids from sponge, scaffolds for the inhibition of human immunodeficiency virus (hiv)

    KAUST Repository

    O'Rourke, Aubrie; Kremb, Stephan; Voolstra, Christian R.

    2016-01-01

    Anti-viral compounds with low cytotoxicity are identified from screening of products found in Red Sea sponges, including the sponge Stylissa carteri. The identified compounds can be brominated pyrrole-2- aminoimidazole alkaloids and derivatives

  12. 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.

  13. 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.

  14. 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.

  15. 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.

  16. 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....

  17. 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.

  18. Safety concerns of herbal products and traditional Chinese herbal medicines: Dehydropyrrolizidine alkaloids and aristolochic acid

    Science.gov (United States)

    In many countries, including the United States, herbal supplements, tisanes and vegetable products, including traditional Chinese medicines, are largely unregulated and their content is not registered, monitored or verified. Consequently, potent plant toxins including dehydropyrrolizidine alkaloids ...

  19. Safety concerns of herbal products and traditional Chinese herbal medicines: Dehydopyrrolizidine alkaloids and aristolochic acid

    Science.gov (United States)

    In many countries, including the United States, herbal supplements, tisanes and vegetable products including traditional Chinese medicines are largely unregulated and their content is not registered, monitored or verified. Consequently potent plant toxins including dehydopyrrolizidine alkaloids and...

  20. Somatic Embryogenesis, Rhizogenesis, and Morphinan Alkaloids Production in Two Species of Opium Poppy

    Directory of Open Access Journals (Sweden)

    My Abdelmajid Kassem

    2001-01-01

    Morphine was only detected in aerial parts of Papaver somniferum album. Codeine and thebaine were detected in the rhizogenous but no embryonic callus. These results suggest that root organogenesis is causally related to alkaloid biosynthesis.

  1. 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.

  2. 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.

  3. Pharmacokinetics and In Vitro Blood-Brain Barrier Screening of the Plant-Derived Alkaloid Tryptanthrin.

    Science.gov (United States)

    Jähne, Evelyn A; Eigenmann, Daniela E; Sampath, Chethan; Butterweck, Veronika; Culot, Maxime; Cecchelli, Roméo; Gosselet, Fabien; Walter, Fruzsina R; Deli, Mária A; Smieško, Martin; Hamburger, Matthias; Oufir, Mouhssin

    2016-07-01

    The indolo[2,1-b]quinazoline alkaloid tryptanthrin was previously identified as a potent anti-inflammatory compound with a unique pharmacological profile. It is a potent inhibitor of cyclooxygenase-2, 5-lipooxygenase-catalyzed leukotriene synthesis, and nitric oxide production catalyzed by the inducible nitric oxide synthase. To characterize the pharmacokinetic properties of tryptanthrin, we performed a pilot in vivo study in male Sprague-Dawley rats (2 mg/kg bw i. v.). Moreover, the ability of tryptanthrin to cross the blood-brain barrier was evaluated in three in vitro human and animal blood-brain barrier models. Bioanalytical UPLC-MS/MS methods used were validated according to current international guidelines. A half-life of 40.63 ± 6.66 min and a clearance of 1.00 ± 0.36 L/h/kg were found in the in vivo pharmacokinetic study. In vitro data obtained with the two primary animal blood-brain barrier models showed a good correlation with an immortalized human monoculture blood-brain barrier model (hBMEC cell line), and were indicative of a high blood-brain barrier permeation potential of tryptanthrin. These findings were corroborated by the in silico prediction of blood-brain barrier penetration. P-glycoprotein interaction of tryptanthrin was assessed by calculation of the efflux ratio in bidirectional permeability assays. An efflux ratio below 2 indicated that tryptanthrin is not subjected to active efflux. Georg Thieme Verlag KG Stuttgart · New York.

  4. 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...

  5. 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.

  6. 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.

  7. 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.

  8. 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.

  9. 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.

  10. 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.

  11. 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.

  12. 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.

  13. 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

  14. 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.

  15. 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.

  16. 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.

  17. 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.

  18. 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

  19. 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.

  20. 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.

  1. [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.

  2. A Convergent Enantioselective Total Synthesis of (-)-Perhydrohistrionicotoxin with an Intramolecular Imino Ene-type Reaction as a Key Step

    DEFF Research Database (Denmark)

    Tanner, David Ackland; Hagberg, Lars

    1998-01-01

    A convergent enantioselective total synthesis of the neurotoxic spirocyclic alkaloid (-)-perhydrohistrionicotoxin (2) is described. A Lewis acid-mediated intramolecular imine ene-type reaction was used for the key spirocyclisation step (14 to 3, with 3 being obtained as a single diastereoisomer...

  3. [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.

  4. 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.

  5. Search for alkaloids on callus culture of Passiflora alata

    Directory of Open Access Journals (Sweden)

    Michelli Wesz Machado

    2010-08-01

    Full Text Available Preliminary work on Passiflora alata leaves failed to detect harmane alkaloids using LC. The aim of this work was to investigate the production of harmane alkaloids through the cell culture of P. alata, inducing its precursor (L-tryptophan. The leaf explants presented satisfactory results after disinfection, and the callus formation was initiated in MS media with adequate quantities of phytohormones. Sixty days after inoculation, calli were inoculated in the optimized semi-solid MS media, with and without the addition of L-tryptophan (50, 100, 200 mg/L and kept in standard conditions for 90 days. Calli were collected on days 6, 16, 26, 36, and 90, followed by acid-base extraction, and analysed by LC. The results showed an absence of harmane, harmin, harmol, harmalol, and harmaline. With L-tryptophan feeding, two peaks were detected, collected and analysed through positive mode electrospray [ESI(+-MS] and sequential analysis in tandem ESI(+-MS/MS. The spectra obtained were very similar, with a repetition of the more intense ions, and consecutive loss of 68 Da units, attributed to the heterocycle pyrazole. It appeared that this transformation was not related to any enzymatic pathway previously described for the plant from L-tryptophan, and the biosynthesis of β-carboline alkaloids in callus culture of P. alata were not observed in this work.As folhas de varias espécies de Passiflora são utilizadas como ansioliticas e sedativas. Passiflora alata Curtis, Passifloraceae consta em três edições da farmacopéia brasileira, porem não há muitos estudos sobre sua composição química. No passado, enfatizava-se a ação conjunta de alcalóides e flavonóides. Em trabalho anterior, não foi detectada a presença de alcalóides harmanicos através de CLAE. Assim, decidiu-se investigar a produção dos mesmos através de cultivo celular, introduzindo seu precursor metabólico L-triptofano. Os explantes foliares apresentaram resultados satisfatorios

  6. 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 ...

  7. 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.

  8. 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.

  9. 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.

  10. [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.

  11. 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.

  12. 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.

  13. 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

  14. Anti-Allergic Properties of Curine, a Bisbenzylisoquinoline Alkaloid

    Directory of Open Access Journals (Sweden)

    Jaime Ribeiro-Filho

    2015-03-01

    Full Text Available Curine is a bisbenzylisoquinoline alkaloid isolated from Chondrodendron platyphyllum (Menispermaceae. Recent findings have shed light on the actions of curine in different models of allergy and inflammation. Here we review the properties and mechanisms of action of curine focusing on its anti-allergic effects. Curine pre-treatment significantly inhibited the scratching behavior, paw edema and systemic anaphylaxis induced by either ovalbumin (OVA in sensitized animals or compound 48/80, through mechanisms of mast cell stabilization and inhibition of mast cell activation to generate lipid mediators. In addition, oral administration of curine significantly inhibited eosinophil recruitment and activation, as well as, OVA-induced airway hyper-responsiveness in a mouse model of asthma, through inhibition of the production of IL-13 and eotaxin, and of Ca2+ influx. In conclusion, curine exhibit anti-allergic effects in models of lung, skin and systemic allergy in the absence of significant toxicity, and as such has the potential for anti-allergic drug development.

  15. Labelled precursors for biosynthetic studies on naphthylisoquinoline alkaloids

    International Nuclear Information System (INIS)

    Bringmann, Gerhard; Pokorny, Frank; Wenzel, Matthias; Wurm, Kathi; Schneider, Christoph

    1997-01-01

    The isotope labelled monocyclic ketones 5 and 8, postulated precursors to the presumably acetogenic naphthylisoquinoline alkaloids, have been synthesized for biogenetic experiments to Ancistrocladaceae and Dioncophyllaceae plants. Key step of the preparation of 1-(2'-[carbonyl- 14 C] acetyl-3',5'-dibenzyloxyphenyl-2-propanone ([ 14 C]-13 is the C-acetylation of the arylpropanone 10 with the mixed pivalic acetic anhydride ([ 14 C]-11). The resulting pyrylium salt [ 14 C]-12, which is stable and can be stored, is cleaved directly before the feeding experiment to give the diketone [ 14 C]-13 and deprotected to give the free phenolic target molecule [ 14 C]-5. This synthetic route is applicable also to the preparation of 1-(2'-[ 13 C 2 ]acetyl-3'hydroxyphenyl)-2-propanone ([ 13 C 2 ]-5) for biosynthetic experiments with NMR analysis. For the preparation of the oxygen-poorer 13 C-labelled diketone 1-(2'-[methyl- 13 C] acetyl-3'-hydr oxyphenyl)-2-propanone [ 13 C]-8, an 'indanone-route' has been elaborated. (Author)

  16. Growth inhibitory alkaloids from mesquite (Prosopis juliflora (Sw.) DC.) leaves.

    Science.gov (United States)

    Nakano, Hiroshi; Nakajima, Eri; Hiradate, Syuntaro; Fujii, Yoshiharu; Yamada, Kosumi; Shigemori, Hideyuki; Hasegawa, Koji

    2004-03-01

    Plant growth inhibitory alkaloids were isolated from the extract of mesquite [Prosopis juliflora (Sw.) DC.] leaves. Their chemical structures were established by ESI-MS, 1H and 13C NMR spectra analysis. The I50 value (concentration required for 50% inhibition of control) for root growth of cress (Lepidium sativum L.) seedlings was 400 microM for 3''''-oxo-juliprosopine, 500 microM for secojuliprosopinal, and 100 microM for a (1:1) mixture of 3-oxo-juliprosine and 3'-oxo-juliprosine, respectively. On the other hand, the minimum concentration exhibiting inhibitory effect on shoot growth of cress seedlings was 10 microM for 3''''-oxo-juliprosopine, 100 microM for secojuliprosopinal, and 1 microM for a (1:1) mixture of 3-oxo-juliprosine and 3'-oxo-juliprosine, respectively. Among these compounds, a (1:1) mixture of 3-oxo-juliprosine and 3'-oxo-juliprosine exhibited the strongest inhibitory effect on the growth of cress seedlings.

  17. Pyrrolizidine Alkaloids: Metabolic Activation Pathways Leading to Liver Tumor Initiation.

    Science.gov (United States)

    Fu, Peter P

    2017-01-17

    Pyrrolizidine alkaloids (PAs) and PA N-oxides are a class of phytochemical carcinogens contained in over 6000 plant species spread around the world. It has been estimated that approximately half of the 660 PAs and PA N-oxides that have been characterized are cytotoxic, genotoxic, and tumorigenic. It was recently determined that a genotoxic mechanism of liver tumor initiation mediated by PA-derived DNA adducts is a common metabolic activation pathway of a number of PAs. We proposed this set of PA-derived DNA adducts could be a common biological biomarker of PA exposure and a potential biomarker of PA-induced liver tumor formation. We have also found that several reactive secondary pyrrolic metabolites can dissociate and interconvert to other secondary pyrrolic metabolites, resulting in the formation of the same exogenous DNA adducts. This present perspective reports the current progress on these new findings and proposes future research needed for obtaining a greater understanding of the role of this activation pathway and validating the use of this set of PA-derived DNA adducts as a biological biomarker of PA-induced liver tumor initiation.

  18. Identification of Toxic Pyrrolizidine Alkaloids and Their Common Hepatotoxicity Mechanism

    Directory of Open Access Journals (Sweden)

    Xinmiao Yan

    2016-03-01

    Full Text Available Pyrrolizidine Alkaloids (PAs are currently one of the most important botanical hepatotoxic ingredients. Glutathion (GSH metabolism is the most reported pathway involved in hepatotoxicity mechanism of PAs. We speculate that, for different PAs, there should be a common mechanism underlying their hepatotoxicity in GSH metabolism. Computational methods were adopted to test our hypothesis in consideration of the limitations of current experimental approaches. Firstly, the potential targets of 22 PAs (from three major PA types in GSH metabolism were identified by reverse docking; Secondly, glutathione S-transferase A1 (GSTA1 and glutathione peroxidase 1 (GPX1 targets pattern was found to be a special characteristic of toxic PAs with stepwise multiple linear regressions; Furthermore, the molecular mechanism underlying the interactions within toxic PAs and these two targets was demonstrated with the ligand-protein interaction analysis; Finally, GSTA1 and GPX1 were proved to be significant nodes in GSH metabolism. Overall, toxic PAs could be identified by GSTA1 and GPX1 targets pattern, which suggests their common hepatotoxicity mechanism: the interfering of detoxication in GSH metabolism. In addition, all the strategies developed here could be extended to studies on toxicity mechanism of other toxins.

  19. Identification of Toxic Pyrrolizidine Alkaloids and Their Common Hepatotoxicity Mechanism.

    Science.gov (United States)

    Yan, Xinmiao; Kang, Hong; Feng, Jun; Yang, Yiyan; Tang, Kailin; Zhu, Ruixin; Yang, Li; Wang, Zhengtao; Cao, Zhiwei

    2016-03-07

    Pyrrolizidine Alkaloids (PAs) are currently one of the most important botanical hepatotoxic ingredients. Glutathion (GSH) metabolism is the most reported pathway involved in hepatotoxicity mechanism of PAs. We speculate that, for different PAs, there should be a common mechanism underlying their hepatotoxicity in GSH metabolism. Computational methods were adopted to test our hypothesis in consideration of the limitations of current experimental approaches. Firstly, the potential targets of 22 PAs (from three major PA types) in GSH metabolism were identified by reverse docking; Secondly, glutathione S-transferase A1 (GSTA1) and glutathione peroxidase 1 (GPX1) targets pattern was found to be a special characteristic of toxic PAs with stepwise multiple linear regressions; Furthermore, the molecular mechanism underlying the interactions within toxic PAs and these two targets was demonstrated with the ligand-protein interaction analysis; Finally, GSTA1 and GPX1 were proved to be significant nodes in GSH metabolism. Overall, toxic PAs could be identified by GSTA1 and GPX1 targets pattern, which suggests their common hepatotoxicity mechanism: the interfering of detoxication in GSH metabolism. In addition, all the strategies developed here could be extended to studies on toxicity mechanism of other toxins.

  20. 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

  1. 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.

  2. Pyrrolizidine Alkaloid-Protein Adducts: Potential Non-invasive Biomarkers of Pyrrolizidine Alkaloid-Induced Liver Toxicity and Exposure.

    Science.gov (United States)

    Xia, Qingsu; Zhao, Yuewei; Lin, Ge; Beland, Frederick A; Cai, Lining; Fu, Peter P

    2016-08-15

    Pyrrolizidine alkaloids (PAs) are phytochemicals present in hundreds of plant species from different families widely distributed in many geographical regions around the world. PA-containing plants are probably the most common type of poisonous plants affecting livestock, wildlife, and humans. There have been many large-scale human poisonings caused by the consumption of food contaminated with toxic PAs. PAs require metabolic activation to generate pyrrolic metabolites to exert their toxicity. In this study, we developed a novel method to quantify pyrrole-protein adducts present in the blood. This method involves the use of AgNO3 in acidic ethanol to cleave the thiol linkage of pyrrole-protein (DHP-protein) adducts, and the resulting 7,9-di-C2H5O-DHP is quantified by HPLC-ES-MS/MS multiple reaction monitoring analysis in the presence of a known quantity of isotopically labeled 7,9-di-C2D5O-DHP internal standard. Using this method, we determined that diester-type PAs administered to rats produced higher levels of DHP-protein adducts than other types of PAs. The results suggest that DHP-protein adducts can potentially serve as minimally invasive biomarkers of PA exposure.

  3. 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.

  4. 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.

  5. 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.

  6. 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.

  7. 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.

  8. 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.

  9. 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.

  10. 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.

  11. Synthesis and Evaluation of Strychnos Alkaloids as MDR Reversal Agents for Cancer Cell Eradication

    Science.gov (United States)

    2014-01-01

    followed by magnesium in MeOH to afford 11 in 75% yield (one-pot). Alkylation with (Z)-2-iodobutenyl bromide23 and acyla- tion with bromoacetyl chloride...eluting with MeOH/CH2Cl2 (0.4:9.6? 1:9). The material was washed with a solution of 25% aq NaOH (10 mL), which afforded 24 mg (71%) of Table 2...with MeOH/CH2Cl2 (0.4:9.6? 1:9). The material was washed with a solution of 25% aq NaOH (10 mL), which afforded 90 mg (86%) of 2 as yellow liquid

  12. Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine

    Digital Repository Service at National Institute of Oceanography (India)

    Parvatkar, P.T.; Parameswaran, P.S.; Tilve, S.G.

    , mostly of children under 5 years, justifying its classification as a dreaded infectious disease along with tuberculosis and AIDS [5]. The roots of the West African plant Cryptolepis sanguinolenta [6 - 19] has long been used in folk medicine...

  13. 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.

  14. Combining Organometallic Catalysis and Organocatalysis for the Synthesis of Heterocyclic Scaffolds

    DEFF Research Database (Denmark)

    Hansen, Casper Lykke

    The main work presented in this thesis describes the development of efficient and novel methodologies for the synthesis of pharmaceutically interesting indolecontaining alkaloids, i.e., the 1,2,3,4-tetrahydro-β-carboline and the 1,2,3,4-tetrahydrocarbazole scaffolds. The synthesis of 1...... to the nitrogen in the allylic system proved to be highly important for the enantioselectivity. Enantiomeric excesses up to 57% was obtained. The synthesis of 1,2,3,4-tetrahydrocarbazole relied on novel Brønsted acidcatalyzed Friedel-Crafts-type reactions. Three different kinds of 1,2,3,4-tetrahydrocarbazole...

  15. A Tryptoline Ring-Distortion Strategy Leads to Complex and Diverse Biologically Active Molecules from the Indole Alkaloid Yohimbine.

    Science.gov (United States)

    Paciaroni, Nicholas G; Ratnayake, Ranjala; Matthews, James H; Norwood, Verrill M; Arnold, Austin C; Dang, Long H; Luesch, Hendrik; Huigens, Robert W

    2017-03-28

    High-throughput screening (HTS) is the primary driver to current drug-discovery efforts. New therapeutic agents that enter the market are a direct reflection of the structurally simple compounds that make up screening libraries. Unlike medically relevant natural products (e.g., morphine), small molecules currently being screened have a low fraction of sp 3 character and few, if any, stereogenic centers. Although simple compounds have been useful in drugging certain biological targets (e.g., protein kinases), more sophisticated targets (e.g., transcription factors) have largely evaded the discovery of new clinical agents from screening collections. Herein, a tryptoline ring-distortion strategy is described that enables the rapid synthesis of 70 complex and diverse compounds from yohimbine (1); an indole alkaloid. The compounds that were synthesized had architecturally complex and unique scaffolds, unlike 1 and other scaffolds. These compounds were subjected to phenotypic screens and reporter gene assays, leading to the identification of new compounds that possessed various biological activities, including antiproliferative activities against cancer cells with functional hypoxia-inducible factors, nitric oxide inhibition, and inhibition and activation of the antioxidant response element. This tryptoline ring-distortion strategy can begin to address diversity problems in screening libraries, while occupying biologically relevant chemical space in areas critical to human health. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Pyrrolizidine alkaloids in food: a spectrum of potential health consequences.

    Science.gov (United States)

    Edgar, J A; Colegate, S M; Boppré, M; Molyneux, R J

    2011-03-01

    Contamination of grain with 1,2-dehydropyrrolizidine ester alkaloids (dehydroPAs) and their N-oxides is responsible for large incidents of acute and subacute food poisoning, with high morbidity and mortality, in Africa and in central and south Asia. Herbal medicines and teas containing dehydroPAs have also caused fatalities in both developed and developing countries. There is now increasing recognition that some staple and widely consumed foods are sometimes contaminated by dehydroPAs and their N-oxides at levels that, while insufficient to cause acute poisoning, greatly exceed maximum tolerable daily intakes and/or maximum levels determined by a number of independent risk assessment authorities. This suggests that there may have been cases of disease in the past not recognised as resulting from dietary exposure to dehydroPAs. A review of the literature shows that there are a number of reports of liver disease where either exposure to dehydroPAs was suspected but no source was identified or a dehydroPA-aetiology was not considered but the symptoms and pathology suggests their involvement. DehydroPAs also cause progressive, chronic diseases such as cancer and pulmonary arterial hypertension but proof of their involvement in human cases of these chronic diseases, including sources of exposure to dehydroPAs, has generally been lacking. Growing recognition of hazardous levels of dehydroPAs in a range of common foods suggests that physicians and clinicians need to be alert to the possibility that these contaminants may, in some cases, be a possible cause of chronic diseases such as cirrhosis, pulmonary hypertension and cancer in humans.

  17. Huperzine alkaloids from Australasian and southeast Asian Huperzia.

    Science.gov (United States)

    Lim, Wei-Han; Goodger, Jason Q D; Field, Ashley R; Holtum, Joseph A M; Woodrow, Ian E

    2010-09-01

    The pharmaceutical alkaloid huperzine A (HupA), currently used in herbal supplements and medicines worldwide, is predominantly sourced from the Chinese lycopod Huperzia serrata (Thunb. ex Murray) Trev. (Lycopodiaceae), which on average contains only 0.08 mg HupA g(-1) dry weight, and is experiencing a rapid decline in China due to over-harvesting. To find a high-yielding, natural source of HupA and/or the related huperzine B (HupB) that could potentially be used as the starting material in a commercial propagation program. We surveyed 17 Huperzia species (15 indigenous to Australia and southeast Asia) for their foliar HupA and HupB concentrations. We also studied intra-specific variation for the huperzines in four species that were available in sufficient numbers, and determined tissue-specific accumulation in larger specimens. HupA was detected in 11 Australasian and southeast Asian species, with eight also containing HupB, albeit at much lower concentrations. A H. elmeri (Herter) Holub plant from the Philippines had one of the highest HupA concentrations recorded (1.01 mg g(-1) dry wt) and it also had the highest HupB content of all plants surveyed (0.34 mg g(-1) dry wt). Intra-specific HupA and HupB concentrations were extremely variable, and at the intra-plant level, reproductive strobili were found to accumulate the highest HupA concentrations. Select Huperzia species from Australia and southeast Asia have potential as the starting material for establishing commercial HupA plantations, but the high intra-specific variability observed suggests that detailed screening is needed to isolate high huperzine-yielding individuals.

  18. Oral toxicity study of certain plant extracts containing pyrrolizidine alkaloids.

    Science.gov (United States)

    Şeremet, Oana Cristina; Bărbuceanu, Florica; Ionică, Floriana Elvira; Margină, Denisa Marilena; GuŢu, Claudia Maria; Olaru, Octavian Tudorel; Ilie, Mihaela; Gonciar, Veaceslav; Negreş, Simona; ChiriŢă, Cornel

    2016-01-01

    Pyrrolizidine alkaloids (PAs) are a class of toxic compounds which are found in plants. Poisoning caused by these toxins is associated with acute and chronic liver damage. Tussilago farfara (coltsfoot), Petasites hybridus (common butterbur), Senecio vernalis (eastern groundsel) and Symphytum officinale (comfrey) are traditional phytotherapic species, which beside the therapeutic bioactive compounds contain PAs. The aim of the paper was to assess the safety of some dry extracts obtained from these species. For the determination of acute toxicity, Organization for Economic Cooperation and Development (OECD) Guideline No. 423 was used. For the determination of repeated dose oral toxicity, Senecionis vernalis herba and Symphyti radix extracts (250 mg÷kg) were administrated, by gavage, for 28 days, and their effects on animal weight, liver and biliary functions, hepatic tissue and oxidative stress were investigated. After the acute toxicity testing, the dry extracts were placed in the GHS Category V (LD50>5000 mg÷kg, p.o.). For the subacute toxicity testing, no death or any signs of toxicity were observed. Also, no significant differences in biochemical parameters were observed between control and treated groups. The observed histopathological lesions were non-specific and were not consistent with the data reported in the literature for PAs exposure. In conclusion, the administration for 28 days, of the tested extracts, in a dose which correspond to a PAs concentration over the limits imposed in some countries, produced no hepatic and biliary toxic effects. Further studies, extended over a longer period of time, are needed in order to determine the safety of plant extracts containing PAs.

  19. 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

  20. 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...

  1. 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

  2. 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.

  3. Pyrrolizidine Alkaloids from Symphytum sylvaticum Boiss. subsp. sepulcrale. (Boiss.& Bal.) Greuter & Burdetvar. sepulcrale and Symphytum aintabicum Hub.- Mor. & Wickens

    OpenAIRE

    KURUCU, Semra; KARTAL, Murat

    2002-01-01

    Pyrrolizidine alkaloid (Echimidine-N-oxide) was isolated from Symphytum sylvaticum Boiss. subsp. sepulcrale (Boiss. & Bal.) Greuter & Burdet var. sepulcrale and pyrrolizidine alkaloid (Echimidine) was isolated from Symphytum aintabicum Hub. - Mor. & Wickens. The structures of the isolated compounds were elucidated based on IR, EIMS, 1H, and 13C NMR analysis and also on 2D NMR (COSY, HMBC, HMQC) experiments.

  4. Divergent Synthesis of Solanidine and 22-epi-Solanidine.

    Science.gov (United States)

    Hou, Ling-Li; Shi, Yong; Zhang, Zhi-Dan; Wu, Jing-Jing; Yang, Qing-Xiong; Tian, Wei-Sheng

    2017-07-21

    A divergent synthesis of solanidine and 22-epi-solanidine, two 25S natural steroidal alkaloids, from 25R-configured diosgenin acetate, is described. Initially, solanidine was synthesized through a series of transformations including a cascade ring-switching process of furostan-26-acid, an epimerization of C25 controlled by the conformation of six-membered lactone ring, an intramolecular Schmidt reaction, and an imine reduction/intramolecular aminolysis process. To address the epimerization issue during Schmidt reaction, an improved synthesis was developed, which also led to a synthesis of 22-epi-solanidine. In this synthesis, selective transformation of azido lactone to azido diol and amino diol was realized through a reduction relay tactic. The azido diol was transformed to solanidine via an intramolecular Schmidt reaction/N-alkylation/reduction process and to 22-epi-solanidine via an intramolecular double N-alkylation process.

  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. 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.

  7. 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.

  8. 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)

  9. 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.

  10. 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.

  11. 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.

  12. 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.

  13. 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.

  14. Main Alkaloids of Peganum harmala L. and Their Different Effects on Dicot and Monocot Crops

    Directory of Open Access Journals (Sweden)

    Chi Zhang

    2013-02-01

    Full Text Available Alkaloids with allelopathic activity are not as well-known as other allelochemicals. Our study revealed that total alkaloids from seeds of the medicinal plant Peganum harmala L. possessed significant growth inhibitory effect on four treated plants, with dicot plants (lettuce and amaranth being more sensitive than the tested monocot plants (wheat and ryegrass. Further investigation led to the isolation of harmaline and harmine as the main active ingredients in the total alkaloids of P. harmala seeds. Harmaline exerted potent inhibitory effects on seedling growth of treated plants, especially dicots, inhibiting root elongation of lettuce and amaranth by 31% and 47% at a very low concentration (5 µg/mL, whereas harmine exhibited much weaker non-selective inhibitory effect on the plants. Considering the high yield and poor utilization of P. harmala in China, we anticipate that this plant could be exploited as an alternative weed management tool in the future.

  15. 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.

  16. 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

  17. 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.

  18. Synthesis of C3/C1-Substituted Tetrahydroisoquinolines

    Directory of Open Access Journals (Sweden)

    Mohamed Mihoubi

    2015-08-01

    Full Text Available A broad biological screening of the natural alkaloid N-methylisosalsoline (2 extracted from Hammada scoparia leaves against a panel of human and parasitic proteases revealed an interesting activity profile of 2 towards human 20S proteasome. This outcome suggests that the 1,2,3,4-tetrahydroisoquinoline skeleton may be exploited as a template for the development of novel anticancer agents. In this article, we report the synthesis and chemical characterization of a new series of isosalsoline-type alkaloids (10–11 with variations at N2 and C3 positions with respect to the natural Compound 2, obtained by a synthetic strategy that involves the Bischler-Napieralski cyclization. The substrate for the condensation to the tetrahydroisoquinoline system, i.e., a functionalized β-arylethyl amine, was obtained through an original double reduction of nitroalkene. The synthetic strategy can be directed to the construction of highly substituted and functionalized 1,2,3,4-tetrahydroisoquinolines.

  19. 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.

  20. 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.

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. [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.

  6. 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.

  7. 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 ...

  8. 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.

  9. 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

  10. 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.

  11. 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)

  12. 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.

  13. 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)

  14. 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

  15. Toxic pyrrolizidine alkaloids in herbal medicines commonly used in Ghana.

    Science.gov (United States)

    Letsyo, Emmanuel; Jerz, Gerold; Winterhalter, Peter; Beuerle, Till

    2017-04-18

    Herbal medicines have been used for centuries for the management and treatment of various ailments due to the belief that they pose only little or no health risk and side effects, and also, in part, due to their availability, affordability and/or self-supply. However, the increasing information over the recent years on the occurrence of pyrrolizidine alkaloids (PAs) in honey, herbal food and tea products has raised concerns about the safety of herbal medicines with respect to contamination. To this day, little is known on the occurrence of toxic PAs in herbal medicines, especially in tropical West Africa. The aim of this study was therefore to determine the PA content of 70 well-known and widely patronized plant-derived medicinal preparations, which are commercialized in Ghana and some West African countries, in order to ascertain their potential health risk. PAs of the herbal medicinal products, sourced from specialized drugstores and mostly regulatory approved, were analyzed for their PA content by a HPLC-ESI-MS/MS sum parameter method. The results show that a total of 60% of the analyzed herbal products were PA positive, indicating an average PA-concentration of 25.0μg/kg. The maximum PA level (1290.0μg/kg) was attributed to a regulatory-approved herbal medicine not known, according to the list of declared ingredients, to contain PA-plant parts. Interestingly, higher PA content (average, 30.2μg/kg) was detected in regulatory-approved herbal medicines, in contrast to lower amount (average, 8.0μg/kg) detected in non-regulatory-approved products. The findings of this study clearly demonstrate that herbal medicines containing PA plants as ingredients, as well as some of those containing plant species not known to produce PAs, are likely to contain hepatotoxic PA at levels higher than the daily dose in food and herbal medicinal products proposed by the European Medicines Agency (i.e. 0.35μg PA per day for 50kg adult and 0.14μg PA per day for 20kg children

  16. Detection of pyrrolizidine alkaloids in German licensed herbal medicinal teas.

    Science.gov (United States)

    Schulz, M; Meins, J; Diemert, S; Zagermann-Muncke, P; Goebel, R; Schrenk, D; Schubert-Zsilavecz, M; Abdel-Tawab, M

    2015-06-01

    Because of the hepatotoxic, mutagenic, and cancerogenic effects of pyrrolizidine alkaloids (PAs) the German Federal Institute for Risk Assessment (BfR) recommends not to exceed a daily PA intake of 0.007 µg/kg body weight (0.42 µg/60 kg adult). In a recent study conducted by the BfR, up to 5647 µg PA/kg dried herbal material were detected in tea products marketed as food. The present study aimed at elucidating whether medicinal teas licensed or registered as medicinal products contain PAs as well. One hundred sixty-nine different commercially available medicinal teas, i.e. 19 nettle (Urtica dioica L.), 12 fennel (Foeniculum vulgare Mill.), 14 chamomile (Matricaria recutita L.), 11 melissa (Melissa officinalis L.) and 4 peppermint (Mentha piperita L.) teas as well as 109 tea mixtures were analyzed for the presence of 23 commercially available PAs. LC/MS was used for the determination of the PAs In general, the total PA contents ranging 0-5668 µg/kg. Thirty percent of the tested single-ingredient tea products and 56.9% of the tested medicinal tea mixtures were found to contain PA concentrations above the limit of quantification (LOQ) of 10 µg/kg. In 11 medicinal teas PA contents >300 µg/kg dry herb were determined thus exceeding the recommended limit for PA intake by BfR. In addition three products of the investigated tea mixtures revealed extremely high PA contents of 4227, 5137, and 5668 µg/kg. Generally, single-ingredient tea products contained much less or even no detectable amounts of PAs when compared to the tea mixtures. PAs in the range between 13 and 1080 µg/kg were also detected in five analyzed aqueous herbal infusions of the medicinal tea mixture products with the highest PA content. Two out of the five investigated herbal infusions exceeded the recommended BfR limit for PA intake. This study demonstrates clearly that also medicinal teas licensed as medicinal products may partly contain high amounts of PAs exceeding current recommendations. For

  17. 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.

  18. 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.

  19. In vitro antibacterial activity of alkaloid extracts from green, red and ...

    African Journals Online (AJOL)

    African Journal of Biotechnology ... The current study presents the antibacterial effect of the alkaloid extracts of some green, red and brown algae were collected from western coast of Libya, against, Escherichia coli, Salmonella typhi, Klebsiella spp., and Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, ...

  20. 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...

  1. 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)

  2. Anti-tumor potential of total alkaloid extract of Prosopis juliflora DC ...

    African Journals Online (AJOL)

    Jane

    2011-08-15

    Aug 15, 2011 ... Cancer is the second leading cause of death in the world. (Madhusudan and .... formula and from that the percentage of cytotoxicity and IC50 values ... complete media were treated as positive and negative controls, .... Cytotoxic effect of total alkaloid extract of P. juliflora leaves against cancer (black bars).

  3. N-(3-aminopropyl)subergorgamide, a new alkaloid from the gorgonian Paraplexaura sp.

    Science.gov (United States)

    Liu, Fen; Li, Shuo; Ju, Zhi-Ran; Liu, Ting-Ting; Liang, Rui-Yu; Liao, Xiao-Jian; Xu, Shi-Hai

    2015-01-01

    A new alkaloid named N-(3-aminopropyl)subergorgamide (1), along with nine known nitrogen-containing compounds (2-10), was isolated from the organic extract of gorgonian Paraplexaura sp. collected from Zhanjiang in Naozhou Island, South China Sea. Their structures were established by detailed MS and NMR spectroscopic analyses, as well as by comparison with literature data.

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

    Science.gov (United States)

    The cis and trans alkaloids from body extracts of workers and alate queens of the tropical fire ant, Solenopsis geminata (Hymenoptera: Formicidae), were successfully separated by silica gel chromatography, identified, and quantitated by GC-MS analysis. Both workers and alate queens produce primarily...

  5. Risk assessment for pyrrolizidine alkaloids detected in (herbal) teas and plant food supplements

    NARCIS (Netherlands)

    Chen, Lu; Mulder, Patrick P.J.; Louisse, Jochem; Peijnenburg, Ad; Wesseling, Sebas; Rietjens, Ivonne M.C.M.

    2017-01-01

    Pyrrolizidine alkaloids (PAs) are plant metabolites present in some botanical preparations, with especially 1,2-unsaturated PAs being of concern because they are genotoxic carcinogens. This study presents an overview of tumour data on PAs and points of departure (PODs) derived from them,

  6. A new antitumor isoquinoline alkaloid from the marine nudibranch Jorunna funebris

    Digital Repository Service at National Institute of Oceanography (India)

    Fontana, A.; Cavaliere, P.; Wahidullah, S.; Naik, C.G.; Cimino, G.

    A new dimeric isoquinoline alkaloid, jorumycin (3), has been isolated from the skin and the mucus of the Pacific nudibranch Jorunna funebris. The structure has been fully elucidated on the grounds of ESMS data and of an extensive 2D NMR analysis...

  7. Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)

    DEFF Research Database (Denmark)

    Kagiyama, Ippei; Kato, Hikaru; Nehira, Tatsuo

    2016-01-01

    Seven new prenylated indole alkaloids, taichunamides A–G, were isolated from the fungus Aspergillus taichungensis (IBT 19404). Taichunamides A and B contained an azetidine and 4‐pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)‐6‐epi‐stephacidin A. Taichunamides...... these cores within the three species likely arise from an intramolecular hetero Diels–Alder reaction....

  8. Straightforward analytical method to determine opium alkaloids in poppy seeds and bakery products

    NARCIS (Netherlands)

    Lopez Sanchez, Patricia; Pereboom-de Fauw, Diana P.K.H.; Mulder, Patrick P.J.; Spanjer, Martien; Stoppelaar, de Joyce; Mol, Hans G.J.; Nijs, de Monique

    2018-01-01

    A straightforward method to determine the content of six opium alkaloids (morphine, codeine, thebaine, noscapine, papaverine and narceine) in poppy seeds and bakery products was developed and validated down to a limit of quantification (LOQ) of 0.1 mg/kg. The method was based on extraction with

  9. 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.

  10. Leishmanicidal, antiplasmodial and cytotoxic activity of indole alkaloids from Corynanthe pachyceras

    DEFF Research Database (Denmark)

    Staerk, D; Lemmich, E; Christensen, J

    2000-01-01

    -NMR resonances by COSY and NOESY experiments. These and related alkaloids showed pronounced activity against Leishmania major promastigotes (IC50 at the micromolar level) but no significant in vitro antiplasmodial activity (against chloroquine-sensitive Plasmodium falciparum). Cytotoxicity assessed with drug...

  11. Two New Alkaloids from a Marine-derived Fungus Neosartorya fischeri

    Directory of Open Access Journals (Sweden)

    Bin Wu

    2015-04-01

    Full Text Available Investigation of EtOAc extract from the fermentation broth of the fungus Neosartorya fischeri led to the isolation of two novel alkaloids and one known compound with antitumor activity against HL-60 cell lines. Their structures were elucidated mainly by NMR and HR-TOF-MS, as well as on comparison with the reported data.

  12. Isatinones A and B, New Antifungal Oxindole Alkaloids from Isatis costata

    Directory of Open Access Journals (Sweden)

    Nighat Afza

    2007-02-01

    Full Text Available Two new oxindole alkaloids isatinone A (1 and B (2 have been isolated from Isatis costata, along with the known trisindoline. Their structures have been assigned on the basis of spectroscopic techniques and chemical studies. Both new compounds showed significant antifungal activity.

  13. 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.

  14. 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.

  15. In silico Assessment of Drug-like Properties of Alkaloids from Areca ...

    African Journals Online (AJOL)

    Purpose: To investigate in silico the drug-like properties of alkaloids (arecoline, arecaidine, guvacine, guvacoline, isoguvacine, arecolidine and homoarecoline) obtained from the fruits of Areca catechu L (areca nut). Methods: All chemical structures were re-drawn using Chemdraw Ultra 11.0. Furthermore, software including ...

  16. 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.

  17. Apoptosis-inducing effects of distichamine and narciprimine, rare alkaloids of the plant family Amaryllidaceae

    Czech Academy of Sciences Publication Activity Database

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

    2012-01-01

    Roč. 22, č. 19 (2012), s. 6195-6199 ISSN 0960-894X Grant - others:GA MŠk(CZ) ED0007/01/01 Program:ED Institutional research plan: CEZ:AV0Z50380511 Keywords : alkaloid * amaryllidaceae * apoptosis Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 2.338, year: 2012

  18. Heliotropium europaeum Poisoning in Cattle and Analysis of its Pyrrolizidine Alkaloid Profile

    NARCIS (Netherlands)

    Shimshoni, J.A.; Mulder, P.P.J.; Bouznach, A.; Edery, N.; Pasval, I.; Barel, S.; Khaliq, M.A.E.; Perl, S.

    2015-01-01

    Pyrrolizidine alkaloids (PAs) are carcinogenic and genotoxic phytochemicals found exclusively in angiosperms. The ingestion of PA-containing plants often results in acute and chronic toxicities in man and livestock, targeting mainly the liver. During February 2014, a herd of 15-18-month-old

  19. Pyrrolizidine alkaloid-containing toxic plants (Scenecio, Crotalaria, Cynoglossum, Amsinckia, Heliotropium, and Echium spp.)

    Science.gov (United States)

    Pyrrolizidine alkaloid (PA) containing plants are found throughout the world and are probably the most common plant cause of poisoning of livestock, wildlife and humans. PAs are potent liver toxins that under some conditions can be carcinogenic. The objective of this paper is to briefly introduce hi...

  20. Equilibrium Studies on Enantioselective Liquid-Liquid Amino Acid Extraction Using a Cinchona Alkaloid Extractant

    NARCIS (Netherlands)

    Schuur, Boelo; Winkelman, Jozef G. M.; Heeres, Hero J.

    2008-01-01

    The enantioselective extraction of aqueous 3,5-dinitrobenzoyl-R,S-leucine (A(R,S)) by a cinchona alkaloid extractant (C) in 1,2-dichloroethane was studied at room temperature (294 K) in a batch system for a range of intake concentrations (10(-4)-10(-3) mol/L) and pH values (3.8-6.6). The