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Sample records for affect pyrrolizidine alkaloid

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

    NARCIS (Netherlands)

    Joosten, L.; Mulder, P.P.J.; Klinkhamer, P.G.L.; Veen, van 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), propagat

  2. Pyrrolizidine alkaloid poisoning of sheep in New South Wales.

    Science.gov (United States)

    Seaman, J T

    1987-06-01

    Pyrrolizidine alkaloid poisoning of sheep in New South Wales was reviewed, based on the records of the New South Wales Department of Agriculture's Regional Veterinary Laboratories. The plant species causing significant mortalities were Echium plantagineum and Heliotropium europaeum. The syndrome of hepatogenous chronic copper poisoning was more frequently diagnosed than primary pyrrolizidine alkaloid poisoning, particularly when grazing E. plantagineum. The data indicated that adult crossbred ewes were the most commonly affected class of sheep. PMID:3632498

  3. Species by environment interactions affect pyrrolizidine alkaloid expression in Senecio jacobaea, Senecio aquaticus, and their hybrids.

    Science.gov (United States)

    Kirk, Heather; Vrieling, Klaas; Van Der Meijden, Eddy; Klinkhamer, Peter G L

    2010-04-01

    We examined the effects of water and nutrient availability on the expression of the defense pyrrolizidine alkaloids (PAs) in Senecio jacobaea and S. aquaticus. Senecio jacobaea, and S. aquaticus are adapted to different natural habitats, characterized by differing abiotic conditions and different selection pressures from natural enemies. We tested if PA concentration and diversity are plastic over a range of water and nutrient treatments, and also whether such plasticity is dependent on plant species. We also tested the hypothesis that hybridization may contribute to PA diversity within plants, by comparing PA expression in parental species to that in artificially generated F(1) hybrids, and also in later generation natural hybrids between S. jacobaea and S. aquaticus. We showed that total PA concentration in roots and shoots is not dependent on species, but that species determines the pattern of PA diversification. Pyrrolizidine alkaloid diversity and concentration are both dependent on environmental factors. Hybrids produce a putatively novel PA, and this PA is conserved in natural hybrids, that are backcrossed to S. jacobaea. Natural hybrids that are backcrossed several times to S. jacobaea are with regard to PA diversity significantly different from S. jacobaea but not from S. aquaticus, while F(1) hybrids are in all cases more similar to S. jacobaea. These results collectively suggest that PA diversity is under the influence of natural selection. PMID:20309618

  4. Pyrrolizidine alkaloids of senecio sp from Peru

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    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.

  5. Pyrrolizidine alkaloids of Senecio sp from Peru

    International Nuclear Information System (INIS)

    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)

  6. 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)

  7. 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)

  8. Genotoxic and tumorigenic pyrrolizidine alkaloids in Chinese herbal plants

    Institute of Scientific and Technical Information of China (English)

    P.P. Fu; Q. Xia; M.W. Chou; G. Lin

    2005-01-01

    Pyrrolizidine alkaloids are a class of hepatotoxic and tumorigenic compounds detected in Chinese herbal plants,contaminated foods, and dietary supplements. In this review, the sources, toxicity, genotoxicity, tumorigenicity, and the metabolic pathways,particular the activation pathways leading to hepatotoxicity and tumorigenicity, of pyrrolizidine alkaloids are briefly discussed, with a focus on the most recent important findings concerning the genotoxic mechanism by which riddelliine liver tumors. This mechanism involves the formation of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived DNA adducts and may be general to most carcinogenic pyrrolizidine alkaloids.

  9. 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...

  10. Pyrrolizidine alkaloids from Bulgarian species of the genus Senecio

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    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.

  11. Root damage and aboveground herbivory change concentration and composition of pyrrolizidine alkaloids of Senecio jacobaea

    NARCIS (Netherlands)

    Hol, W.H.G.; Macel, M.; Van Veen, J.A.; van der Meijden, E.

    2004-01-01

    Thus far not many studies focussed on how herbivory in one plant part affects plant defence in the other. The effects of root damage and a leaf-feeding herbivore (Mamestra brassicae) on pyrrolizidine alkaloid (PA) levels of Senecio jacobaea were investigated in a controlled environment. Three cloned

  12. Solid-phase extraction and LC-MS analysis of pyrrolizidine alkaloids in honeys.

    Science.gov (United States)

    Beales, Kerrie A; Betteridge, Keith; Colegate, Steven M; Edgar, John A

    2004-10-20

    Strong-cation-exchange, solid-phase extraction of pyrrolizidine alkaloids and their N-oxides from honey samples was followed by reduction of the N-oxides and subsequent analysis of total pyrrolizidine alkaloids using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. A limited survey of 63 preprocessing samples of honey, purposefully biased toward honeys attributed to floral sources known to produce pyrrolizidine alkaloids, demonstrated levels of pyrrolizidine alkaloids up to approximately 2000 parts per billion (ppb) in a sample attributed to Echium plantagineum. Up to 800 ppb pyrrolizidine alkaloids was detected in some honeys not attributed by the collector to any pyrrolizidine alkaloid-producing floral source. No pyrrolizidine alkaloids were detected in approximately 30% of the samples in this limited study, while some honeys showed the copresence of pyrrolizidine alkaloids from multiple floral sources such as E. plantagineum and Heliotropium europaeum. In addition, retail samples of blended honeys (with no labeling to suggest that pyrrolizidine alkaloid-producing floral sources were used in the blends) have been shown to contain up to approximately 250 ppb pyrrolizidine alkaloids. PMID:15479038

  13. Ornithine Decarboxylase, Polyamines, and Pyrrolizidine Alkaloids in Senecio and Crotalaria

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    Birecka, Helena; Birecki, Mieczyslaw; Cohen, Eric J.; Bitonti, Alan J.; McCann, Peter 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. PMID:16665870

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

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    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. PMID:27388689

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

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    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.

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

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    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. PMID:26373269

  17. New records of pyrrolizidine alkaloid-feeding insects. Hemiptera and Coleoptera on Senecio brasiliensis.

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    Klitzke; Trigo

    2000-04-01

    New records are reported for a Hemipteran (Largus rufipennis) and a Coleopteran (Chauliognathus fallax) feeding on Senecio brasiliensis (Asteraceae) and sequestering pyrrolizidine alkaloids (PAs). Both insects are warningly colored and rejected by predators. PMID:10725590

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

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    Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

    2002-06-01

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

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

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    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.

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

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    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.

  1. 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...

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

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

    2015-09-01

    Progress has recently been made in the elucidation of pathways of secondary metabolism. However, because of its diversity, genetic information concerning biosynthetic details is still missing for many natural products. This is also the case for the biosynthesis of pyrrolizidine alkaloids. To close this gap, we tested strategies using tissues that express this pathway in comparison to tissues in which this pathway is not expressed. As many pathways of secondary metabolism are known to be induced by jasmonates, the pyrrolizidine alkaloid-producing species Heliotropium indicum, Symphytum officinale, and Cynoglossum officinale of the Boraginales order were treated with methyl jasmonate. An effect on pyrrolizidine alkaloid levels and on transcript levels of homospermidine synthase, the first specific enzyme of pyrrolizidine alkaloid biosynthesis, was not detectable. Therefore, a method was developed by making use of the often observed cell-specific production of secondary compounds. H. indicum produces pyrrolizidine alkaloids exclusively in the shoot. Homospermidine synthase is expressed only in the cells of the lower leaf epidermis and the epidermis of the stem. Suggesting that the whole pathway of pyrrolizidine alkaloid biosynthesis might be localized in these cells, we have isolated single cells of the upper and lower epidermis by laser-capture microdissection. The resulting cDNA preparations have been used in a subtractive transcriptomic approach. Quantitative real-time polymerase chain reaction has shown that the resulting library is significantly enriched for homospermidine-synthase-coding transcripts providing a valuable source for the identification of further genes involved in pyrrolizidine alkaloid biosynthesis. PMID:26057225

  3. Seasonal variation in pyrrolizidine alkaloid concentration and plant development in Senecio madagascariensis poir. (Asteraceae) in Brazil

    Science.gov (United States)

    This chapter presents the results of studies conducted in the municipality of Eldorado do Sul, State of Rio Grande do Sul, Brazil, in July and October 2007 and January and May 2008 to measure the pyrrolizidine alkaloid (PA) concentrations of S. madagascariensis plant material (including leaves, flow...

  4. 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 mixed-br

  5. EFSA (European Food Safety Authority), 2016. Dietary exposure assessment to pyrrolizidine alkaloids in the European population

    DEFF Research Database (Denmark)

    Petersen, Annette

    Chronic and acute dietary exposure to pyrrolizidine alkaloids (PAs) was estimated in the European population via the consumption of plant-derived foods. This resulted in highest estimates of mean chronic dietary exposure of 34.5–48.4 ng/kg body weight (bw) per day in ‘Toddlers’ (LB–UB) and 154...

  6. Are effects of common ragwort in the Ames test caused by pyrrolizidine alkaloids?

    NARCIS (Netherlands)

    Bovee, T.F.H.; Helsdingen, R.J.R.; Hoogenboom, R.L.A.P.; Nijs, de M.W.C.M.; Liu, Xiaojie; Vrieling, Klaas; Klinkhamer, P.G.L.; Peijnenburg, A.A.C.M.; Mulder, P.P.J.

    2015-01-01

    It has previously been demonstrated by others that acetone extracts of Senecio jacobaea (syn. Jacobaea vulgaris, common or tansy ragwort) test positive in the Salmonella/microsome mutagenicity test (Ames test). Pyrrolizidine alkaloids (PAs) are thought to be responsible for these mutagenic effect

  7. Poisoning of chickens and ducks by pyrrolizidine alkaloids of Heliotropium europaeum.

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

    1979-06-01

    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. PMID:518422

  8. 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. PMID:26027474

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

    Science.gov (United States)

    Stegelmeier, Bryan L

    2011-07-01

    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. This article briefly introduces high-risk North American PA-containing plants, summarizing their toxicity and subsequent pathology. Current diagnostic techniques, treatments, and strategies to avoid losses to PA poisoning are also reviewed. PMID:21575778

  10. Homospermidine in transgenic tobacco results in considerably reduced spermidine levels but is not converted to pyrrolizidine alkaloid precursors.

    Science.gov (United States)

    Abdelhady, Mohamed I S; Beuerle, Till; Ober, Dietrich

    2009-09-01

    Homospermidine synthase is the first specific enzyme in the biosynthesis of pyrrolizidine alkaloids. Whereas the substrates putrescine and spermidine are part of the highly dynamic polyamine pool of plants, the product homospermidine is incorporated exclusively into the necine base moiety of pyrrolizidine alkaloids. Recently, the gene encoding homospermidine synthase has been shown to have been recruited several times independently during angiosperm evolution by the duplication of the gene encoding deoxyhypusine synthase. To test whether high levels of homospermidine suffice for conversion, at least in traces, to precursors of pyrrolizidine alkaloids, transgenic tobacco plants were generated expressing homospermidine synthase. Analyses of the polyamine content revealed that, in the transgenic plants, about 80% of spermidine was replaced by homospermidine without any conspicuous modifications of the phenotype. Tracer-feeding experiments and gas chromatographic analyses suggested that these high levels of homospermidine were not sufficient to explain the formation of alkaloid precursors. These results are discussed with respect to current models of pathway evolution. PMID:19543980

  11. Metabolic Activation of the Tumorigenic Pyrrolizidine Alkaloid, Retrorsine, Leading to DNA Adduct Formation In Vivo

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    Ming W. Chou

    2005-04-01

    Full Text Available Pyrrolizidine alkaloids are naturally occurring genotoxic chemicals produced by a large number of plants. The high toxicity of many pyrrolizidine alkaloids has caused considerable loss of free-ranging livestock due to liver and pulmonary lesions. Chronic exposure of toxic pyrrolizidine alkaloids to laboratory animals induces cancer. This investigation studies the metabolic activation of retrorsine, a representative naturally occurring tumorigenic pyrrolizidine alkaloid, and shows that a genotoxic mechanism is correlated to the tumorigenicity of retrorsine. Metabolism of retrorsine by liver microsomes of F344 female rats produced two metabolites, 6, 7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP, at a rate of 4.8 ± 0.1 nmol/mg/min, and retrorsine-N-oxide, at a rate of 17.6±0.5 nmol/mg/min. Metabolism was enhanced 1.7-fold by using liver microsomes prepared from dexamethasone-treated rats. DHP formation was inhibited 77% and retrorsine N-oxide formation was inhibited 29% by troleandomycin, a P450 3A enzyme inhibitor. Metabolism of retrorsine with lung, kidney, and spleen microsomes from dexamethasone-treated rats also generated DHP and the N-oxide derivative. When rat liver microsomal metabolism of retrorsine occurred in the presence of calf thymus DNA, a set of DHP-derived DNA adducts was formed; these adducts were detected and quantified by using a previously developed 32P-postlabeling/HPLC method. These same DNA adducts were also found in liver DNA of rats gavaged with retrorsine. Since DHP-derived DNA adducts are suggested to be potential biomarkers of riddelliine-induced tumorigenicity, our results indicate that (i similar to the metabolic activation of riddelliine, the mechanism of retrorsine-induced carcinogenicity in rats is also through a genotoxic mechanism involving DHP; and (ii the set of DHP-derived DNA adducts found in liver DNA of rats gavaged with retrorsine or riddelliine can serve as biomarkers for the

  12. 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...

  13. Scientific Opinion on Pyrrolizidine alkaloids in food and feed

    NARCIS (Netherlands)

    Beuerle, T.; Benford, D.; Brimer, L.; Cottrill, B.; Doerge, D.; Dusemund, B.; Farmer, P.; Fürst, P.; Humpf, H.; Mulder, P.P.J.

    2013-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread C

  14. Interspecific transfer of pyrrolizidine alkaloids: An unconsidered source of contaminations of phytopharmaceuticals and plant derived commodities.

    Science.gov (United States)

    Nowak, Melanie; Wittke, Carina; Lederer, Ines; Klier, Bernhard; Kleinwächter, Maik; Selmar, Dirk

    2016-12-15

    Many plant derived commodities contain traces of toxic pyrrolizidine alkaloids (PAs). The main source of these contaminations seems to be the accidental co-harvest of PA-containing weeds. Yet, based on the insights of the newly described phenomenon of the horizontal transfer of natural products, it is very likely that the PA-contaminations may also be due to an uptake of the alkaloids from the soil, previously being leached out from rotting PA-plants. The transfer of PAs was investigated using various herbs, which had been mulched with dried plant material from Senecio jacobaea. All of the acceptor plants exhibited marked concentrations of PAs. The extent and the composition of the imported PAs was dependent on the acceptor plant species. These results demonstrate that PAs indeed are leached out from dried Senecio material into the soil and confirm their uptake by the roots of the acceptor plants and the translocation into the leaves. PMID:27451168

  15. Analysis of pyrrolizidine alkaloids and evaluation of some biological activities of Algerian Senecio delphinifolius (Asteraceae).

    Science.gov (United States)

    Tidjani, Soukaina; Okusa, Philippe N; Zellagui, Amar; Banuls, Laetitia Moreno Y; Stévigny, Caroline; Duez, Pierre; Rhouati, Salah

    2013-04-01

    Although Senecio species are known as sources of potentially toxic pyrrolizidine alkaloids (PAs), some species of this genus are traditionally used as remedies, notably in Algeria. In this paper, the evaluation of biological activities and the analysis of PAs of Algerian specimens of Senecio delphinifolius Vahl are reported. The n-butanolic extract of the herb showed a weak antibacterial effect against Escherichia coli with a MIC of 1 mg/mL, but was inactive against Staphylococcus aureus and Pseudomonas aeruginosa. The n-butanolic extracts of the roots, stems and herb showed a modest antioxidant activity, scavenging the free radical DPPH with respective IC50 values of 55.3, 50.2 and 13.3 microg/mL. A cytotoxic effect against a series of human tumor cell lines was observed with the n-butanolic extract from stems (IC50 ranging between 34 and 88 microg/mL). The herb of the evaluated sample contains 140 ppm of PAs (senecionine, seneciphylline, integerrimine, senkirkine) and PA-related alkaloids (dehydrosenkirkine and neosenkirkine). As the major PAs belong to the toxic series (1,2-unsaturation in the pyrrolizidine cycle and macrocyclic diester), the use of S. delphinifolius should be discouraged in traditional medicine. PMID:23738446

  16. Pyrrolizidine and tropane alkaloids in teas and the herbal teas peppermint, rooibos and chamomile in the Israeli market

    NARCIS (Netherlands)

    Shimshoni, Jakob Avi; Duebecke, Arne; Mulder, Patrick P.J.; Cuneah, Olga; Barel, Shimon

    2015-01-01

    Dehydro pyrrolizidine alkaloids (dehydro PAs) are carcinogenic phytotoxins prevalent in the Boraginaceae, Asteraceae and Fabaceae families. Dehydro PAs enter the food and feed chain by co-harvesting of crops intended for human and animal consumption as well as by carry-over into animal-based prod

  17. Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed

    NARCIS (Netherlands)

    Oplatowska, M.; Elliott, C.T.; Huet, A.C.; McCarthy, M.; Mulder, P.P.J.; Holst, von C.; Delahaut, P.; Egmond, van H.P.; Campbell, K.

    2014-01-01

    Pyrrolizidine alkaloids (PAs) are a group of plant secondary metabolites with carcinogenic and hepatotoxic properties. When PA-producing plants contaminate crops, toxins can be transferred through the food chain and cause illness in humans and animals, most notably hepatic veno-occlusive disease. Ho

  18. Sesquiterpenes, flavonoids, shikimic acid derivatives and pyrrolizidine alkaloids from Senecio kingii Hook.

    Science.gov (United States)

    Ruiz-Vásquez, Liliana; Reina, Matías; López-Rodríguez, M; Giménez, Cristina; Cabrera, Raimundo; Cuadra, Pedro; Fajardo, Víctor; González-Coloma, Azucena

    2015-09-01

    Twenty-four compounds including eleven eremophilanolides (1-11), one eremophilane (13), five shikimic acid derivatives (14-18), six flavonoids (19-24), and the macrocyclic unsaturated pyrrolizidine alkaloid integerrimine (25) were isolated from Senecio kingii, an endemic species from the Magallanes Region (Chile). Compounds 3, 5, 6, 8-11 and 13-18 have not been previously reported as natural products. Their molecular structures were determined by NMR spectroscopic analysis and comparison with published NMR data. An X-ray-analysis of compound 3 has been performed. Their insecticidal and antifungal activities were tested, being compound 3 the strongest insect antifeedant. Compounds 6, 9 and 18 were moderate antifungals. PMID:26101146

  19. Senecio brasiliensis and pyrrolizidine alkaloids: toxicity to animals and human health

    Directory of Open Access Journals (Sweden)

    Helenice de Souza Spinosa

    2013-06-01

    Full Text Available Most economic losses in Brazilian livestock production, especially in horses and cattle, are due to poison plants, such as those of the genus Senecio. Senecio brasiliensis Lessing is the main cause of death in cattle in the state of Rio Grande do Sul. The toxicity of this genus is attributed to their content of pyrrolizidine alkaloids, which undergo liver biotransformation creating toxic metabolites, namely pyrroles. These compounds can be transferred to humans through contaminated animal products or by the use of this plant in folk medicine. Thus, the present article is a review of the species S. brasiliensis, its toxic active principles and the mechanism by which pathogenesis occurs. Other plants with the same toxic principles that are harmful to human health are covered as well.

  20. Pyrrolizidine Alkaloids from Echium vulgare in Honey Originate Primarily from Floral Nectar.

    Science.gov (United States)

    Lucchetti, Matteo A; Glauser, Gaetan; Kilchenmann, Verena; Dübecke, Arne; Beckh, Gudrun; Praz, Christophe; Kast, Christina

    2016-06-29

    Pyrrolizidine alkaloids (PAs) in honey can be a potential human health risk. So far, it has remained unclear whether PAs in honey originate from pollen or floral nectar. We obtained honey, nectar, and plant pollen from two observation sites where Echium vulgare L. was naturally abundant. The PA concentration of honey was determined by targeted analysis using a high pressure liquid chromatography-mass spectrometry system (HPLC-MS/MS), allowing the quantification of six different PAs and PA-N-oxides present in E. vulgare. Echium-type PAs were detected up to 0.153 μg/g in honey. Nectar and plant pollen were analyzed by nontargeted analysis using ultrahigh pressure liquid chromatography-high resolution-mass spectrometry (UHPLC-HR-MS), allowing the detection of 10 alkaloids in small size samples. Echium-type PAs were detected between 0.3-95.1 μg/g in nectar and 500-35000 μg/g in plant pollen. The PA composition in nectar and plant pollen was compared to the composition in honey. Echimidine (+N-oxide) was the main alkaloid detected in honey and nectar samples, while echivulgarine (+N-oxide) was the main PA found in plant pollen. These results suggest that nectar contributes more significantly to PA contamination in honey than plant pollen. PMID:27244472

  1. Chemical Diversity Investigation of Hepatotoxic Pyrrolizidine Alkaloids in Qianliguang (Senecio scandens and Related Species by UHPLC-QTOF-MS

    Directory of Open Access Journals (Sweden)

    Lin Zhu

    2015-04-01

    Full Text Available Objective: Qianliguang (Senecio scandens is a common Chinese medicinal herb. Qianliguang-containing herbal proprietary products are registered as over-the-counter remedies in China and exported to Western countries. The presence of hepatotoxic pyrrolizidine alkaloids (PAs has raised concerns about the safety of using Qianliguang and its products. The present study aims at investigation of different types of PAs present in Qianliguang collected from representative locations in China.

  2. The effect of nutrients on pyrrolizidine alkaloids in Senecio plants and their interactions with herbivores and pathogens.

    Science.gov (United States)

    Hol, W H G

    2011-03-01

    The aim of this review is to combine the knowledge of studies on effects of nutrients on pyrrolizidine alkaloids (PAs) in Senecio with those studies of effects of PAs on herbivores and pathogens in order to predict the effects that nutrients may have on herbivores and pathogens via changes in PAs. We discuss whether these predictions match with the outcome of studies where the effect of nutrients on herbivores and insects were measured. PA concentrations in S. jacobaea, S. vulgaris and S. aquaticus were mostly reduced by NPK fertilization, with genotype-specific effects occurring. Plant organs varied in their response to increased fertilization; PA concentrations in flowers remained constant, while shoot and roots were mostly negatively affected. Biomass change is probably largely responsible for the change in concentrations. Nutrients affect both the variety and the levels of PAs in the plant. The reduced PA concentrations after NPK fertilization was expected to benefit herbivores, but no or negative responses from insect herbivores were observed. Apparently other changes in the plant after fertilization are overriding the effect of PAs. Pathogens do seem to benefit from the lower PA concentrations after fertilization; they were more detrimental to fertilized plants than to unfertilized control plants. Future studies should include the effect of each element of nutrients separately and in combinations in order to gain more insight in the effect of specific nutrients on PA content in Senecio plants. PMID:21475405

  3. Quantitative analysis of total retronecine esters-type pyrrolizidine alkaloids in plant by high performance liquid chromatography

    International Nuclear Information System (INIS)

    Pyrrolizidine alkaloids (PAs) are alkaloids which typically contain a necine (7-hydroxy-1-hydroxymethyl-6,7-dihydro-5H-pyrrolizidine) base unit, and they can be found in one third of the higher plants around the world. They are hepatotoxic, mutagenic and carcinogenic and pose a threat to human health and safety. A specific, quick and sensitive method is therefore needed to detect and quantify the PAs sometimes in trace amount in herbs, tea or food products. Based on high performance liquid chromatography with prior derivatization of the alkaloids using o-chloranil and Ehrlich's reagent, we report an improved method for quantitative analysis of the total amount of retronecine esters-type pyrrolizidine alkaloids (RET-PAs) in a plant extract. The total quantitation of RET-PAs is achieved because of a common colored retronecine marker, a 7-ethoxy-1-ethoxylmethyl retronecine derivative, is produced with all the different RET-PAs during the derivatization reaction. The chemical identity of the common retronecine marker was characterized on-line by positive mode electrospray ionization mass spectrometry and nuclear magnetic resonance spectroscopy. The limit of detection using the improved method is 0.26 nmol mL-1 and the limit of quantitation is 0.79 nmol mL-1. The advantages of this method are much enhanced sensitivity in detection and quantitation, and, no restriction on the choice of RET-PA as a calibration standard. Application of the developed method to the quantitation of total RET esters-type PAs in Senecio scandens from different regions of China is also reported

  4. Field Evaluation of a Novel Pyrrolizidine Alkaloid Attracticide for the Management of Zonocerus variegatus on Cabbage

    Science.gov (United States)

    Timbilla, J. A.; Lawson, B. W.; Yeboah-Gyan, K.

    Cabbage, Brassica oleraceae var. capitata is an important vegetable grown and consumed in Ghana. Apart from infestations of the lepidopterous Plutella xylostella and Hellula undalis resulting from continuous cultivation, a new pest Zonocerus variegatus has been reported to causing damage to the crop. The efficacy of a novel pyrrolizidine alkaloid (PA) based novel PA-attracticide developed from treating the roots of the neophyte, Chromolaena odorata which contains PAs with Carbofuran 3G for the management of Z. variegatus was tested using cabbage as a test crop in field caged plots. Field caged plots of cabbage artificially infested with Z. variegatus were treated with and without PA-attracticide in addition to a control treatment of caged cabbage plot with no insect and PA-attracticide. The experimental design was a RCB replicated three times in two ecological zones. The results showed that the establishment, leaf and head damage of cabbage was statistically the same in the PA-treated plots and the control treatment. These treatments, however, performed significantly better than the treatment without PA-attracticide. The results obtained holds promise for mitigating the menace of the grasshopper on cabbage using PA based attracticides.

  5. Evaluation of Athrixia bush tea for cytotoxicity, antioxidant activity, caffeine content and presence of pyrrolizidine alkaloids.

    Science.gov (United States)

    McGaw, L J; Steenkamp, V; Eloff, J N

    2007-03-01

    In South Africa, Athrixia phylicoides DC. (bush tea) is widely used as a beverage, cough remedy and purgative. The commercialization of this tea in a similar vein to rooibos (Aspalathus linearis), is being considered. Traditional infusions and decoctions, as well as water and ethanol extracts, were prepared and screened. A related species, Athrixia elata Sond. (daisy tea), was included in many of the assays as a comparison. Extracts of Athrixia phylicoides and Athrixia elata were tested for toxic effects to brine shrimp larvae and the Vero kidney cell line. In both assays, the traditional preparations and aqueous extracts had little effect, but the ethanol extracts were relatively toxic. Antioxidant activity comparable to that found in rooibos was established. No detectable levels of caffeine were present in the Athrixia extracts following analysis using TLC and I/HCl spray reagent. Neither screening using spectrophotometry nor confirmation using gas chromatography-mass spectrometry analyses showed evidence of pyrrolizidine alkaloids in Athrixia phylicoides. Although a wider range of studies needs to be conducted prior to commercialization, these results support the development of bush tea as a healthy alternative to caffeine-containing beverages. PMID:17045437

  6. Recombinagenic activity of integerrimine, a pyrrolizidine alkaloid from Senecio brasiliensis, in somatic cells of Drosophila melanogaster.

    Science.gov (United States)

    Campesato, V R; Graf, U; Reguly, M L; de Andrade, H H

    1997-01-01

    Integerrimine (ITR), a pyrrolizidine alkaloid from Senecio brasiliensis, was tested for genotoxicity using the wing somatic mutation and recombination test (SMART) in Drosophila melanogaster. The compound was administered by chronic feeding (48 hours) of 3-day-old larvae. Two different crosses involving the markers flare (flr) and multiple wing hairs (mwh) were used, that is, the standard (ST) cross and the high bioactivation (HB) cross, which has a high cytochrome P450-dependent bioactivation capacity. In both crosses, the wings of two types of progeny were analyzed, that is, inversion-free marker heterozygotes and balancer heterozygotes carrying multiple inversions. ITR was found to be equally potent in inducing spots in a dose-related manner in the marker heterozygotes of both crosses. This indicates that the bioactivation capacity present in larvae of the ST cross is sufficient to reveal the genotoxic activity of ITR. In the balancer heterozygotes of both crosses, where all recombinational events are eliminated due to the inversions, the frequencies of induced spots were considerably reduced which documents the recombinagenic activity of ITR. Linear regression analysis of the dose response relationships for both genotypes shows that 85% to 90% of the wing spots are due to mitotic recombination. PMID:9020312

  7. Heliotropium europaeum poisoning in cattle and analysis of its pyrrolizidine alkaloid profile.

    Science.gov (United States)

    Shimshoni, Jakob Avi; Mulder, Patrick P J; Bouznach, Arieli; Edery, Nir; Pasval, Israel; Barel, Shimon; Abd-El Khaliq, Mohammed; Perl, Samuel

    2015-02-11

    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 mixed-breed beef cattle (n = 73) from the Galilee region in Israel was accidently fed hay contaminated with 12% Heliotropium europaeum (average total PA intake was 33 mg PA/kg body weight/d). After 42 d of feed ingestion, sudden death occurred over a time period of 63 d with a mortality rate of 33%. Necropsy and histopathological examination revealed fibrotic livers and moderate ascites, as well as various degrees of hyperplasia and fibrosis of bile duct epithelial cells. Elevated γ-glutamyl-transferase and alkaline phosphatase levels were indicative of severe liver damage. Comprehensive PA profile determination of the contaminated hay and of native H. europaeum by LC-MS/MS revealed the presence of 30 PAs and PA-N-oxides, including several newly reported PAs and PA-N-oxides of the rinderine and heliosupine class. Heliotrine- and lasiocarpine-type PAs constituted 80% and 18% of the total PAs, respectively, with the N-oxides being the most abundant form (92%). The PA profile of the contaminated hay showed very strong resemblance to that of H. europaeum. PMID:25591008

  8. Quercetin prevents pyrrolizidine alkaloid clivorine-induced liver injury in mice by elevating body defense capacity.

    Directory of Open Access Journals (Sweden)

    Lili Ji

    Full Text Available Quercetin is a plant-derived flavonoid that is widely distributed in nature. The present study is designed to analyze the underlying mechanism in the protection of quercetin against pyrrolizidine alkaloid clivorine-induced acute liver injury in vivo. Serum transaminases, total bilirubin analysis, and liver histological evaluation demonstrated the protection of quercetin against clivorine-induced liver injury. Terminal dUTP nick end-labeling assay demonstrated that quercetin reduced the increased amount of liver apoptotic cells induced by clivorine. Western-blot analysis of caspase-3 showed that quercetin inhibited the cleaved activation of caspase-3 induced by clivorine. Results also showed that quercetin reduced the increase in liver glutathione and lipid peroxidative product malondialdehyde induced by clivorine. Quercetin reduced the enhanced liver immunohistochemical staining for 4-hydroxynonenal induced by clivorine. Results of the Mouse Stress and Toxicity PathwayFinder RT2 Profiler PCR Array demonstrated that the expression of genes related with oxidative or metabolic stress and heat shock was obviously altered after quercetin treatment. Some of the alterations were confirmed by real-time PCR. Our results demonstrated that quercetin prevents clivorine-induced acute liver injury in vivo by inhibiting apoptotic cell death and ameliorating oxidative stress injury. This protection may be caused by the elevation of the body defense capacity induced by quercetin.

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

    International Nuclear Information System (INIS)

    A new method was developed for the preparation of tritiated putrescine dihydrochloride ([2,3-3H]-1,4-diaminobutane dihydro-chloride) from succinonitrile (1,4-butanedinitrile) and 3H2O, with a radiochemical yield of 16%. Tritiated jacobine and other pyrrolizidine alkaloids were then biosynthesized in Senecio jacobaea using 3H-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)

  10. Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): implications for toxicity.

    Science.gov (United States)

    Castells, Eva; Mulder, Patrick P J; Pérez-Trujillo, Míriam

    2014-12-01

    Changes in plant chemical defenses after invasion could have consequences on the invaded ecosystems by modifying the interactions between plants and herbivores and facilitating invasion success. However, no comprehensive biogeographical studies have yet determined the phenotypic levels of plant chemical defenses, as consumed by local herbivores, covering large distributional areas of a species. Senecio pterophorus is a perennial shrub native to Eastern South Africa, expanded into Western South Africa and introduced into Australia and Europe. As other Asteraceae, S. pterophorus contains pyrrolizidine alkaloids (PAs) toxic to vertebrate and invertebrate herbivores. Here we analyzed S. pterophorus PAs by LC-MS/MS on foliage sampled across its entire distributional range, including the native and all non-native areas. PA concentrations and diversity was very high: we found 57 compounds belonging to 6 distinct necine base-types, including the highly toxic 1,2-unsaturated PAs (retronecine and otonecines) and the less toxic 1,2-saturated PAs (platynecine and rosmarinecines). Plants from different origins diverged in their PA absolute and relative concentrations. Rosmarinine was the most abundant compound in Australia and South Africa, but it was nearly absent in Europe. We characterized three plant chemotypes: retrorsine-senkirkine chemotype in Eastern South Africa, rosmarinine chemotype in Australia and Western South Africa, and acetylseneciphylline chemotype in Europe. PA absolute concentrations were highest in Australia. The increased absolute and relative concentrations of retronecine PAs from Australia and Europe, respectively, indicate that S. pterophorus is potentially more toxic in the invasive range than in the native range. PMID:25269662

  11. Testing the generalist-specialist dilemma: the role of pyrrolizidine alkaloids in resistance to invertebrate herbivores in Jacobaea species.

    Science.gov (United States)

    Wei, Xianqin; Vrieling, Klaas; Mulder, Patrick P J; Klinkhamer, Peter G L

    2015-02-01

    Plants produce a diversity of secondary metabolites (SMs) to protect them from generalist herbivores. On the other hand, specialist herbivores use SMs for host plant recognition, feeding and oviposition cues, and even sequester SMs for their own defense. Therefore, plants are assumed to face an evolutionary dilemma stemming from the contrasting effects of generalist and specialist herbivores on SMs. To test this hypothesis, bioassays were performed with F2 hybrids from Jacobaea species segregating for their pyrrolizidine alkaloids (PAs), using a specialist flea beetle (Longitarsus jacobaeae) and a generalist slug (Deroceras invadens). Our study demonstrated that while slug feeding damage was negatively correlated with the concentration of total PAs and that of senecionine-like PAs, flea beetle feeding damage was not affected by PAs. It was positively correlated though, with leaf fresh weight. The generalist slug was deterred by senecionine-like PAs but the specialist flea beetle was adapted to PAs in its host plant. Testing other herbivores in the same plant system, it was observed that the egg number of the specialist cinnabar moth was positively correlated with jacobine-like PAs, while the silver damage of generalist thrips was negatively correlated with senecionine- and jacobine-like PAs, and the pupae number of generalist leaf miner was negatively correlated with otosenine-like PAs. Therefore, while the specialist herbivores showed no correlation whatsoever with PA concentration, the generalist herbivores all showed a negative correlation with at least one type of PA. We concluded that the generalist herbivores were deterred by different structural groups of PAs while the specialist herbivores were attracted or adapted to PAs in its host plants.

  12. Characterization and screening of pyrrolizidine alkaloids and N-oxides from various parts of many botanicals and dietary supplements using liquid chromatography high resolution mass spectrometry

    Science.gov (United States)

    The UHPLC-QToF-MS analysis of pyrrolizidine alkaloids from various parts of 37 botanicals and 7 dietary supplements was performed. A separation by LC was achieved using a reversed-phase column and a gradient of water/acetonitrile each containing formic acid as the mobile phase. MS-MS detection was u...

  13. Stereochemical inversion of pyrrolizidine alkaloids byMechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance.

    Science.gov (United States)

    Trigo, J R; Barata, L E; Brown, K S

    1994-11-01

    Pyrrolizidine alkaloids (PAs), acquired by adults or larvae of Danainae and Ithomiinae butterflies and Arctiidae moths from plants, protect these lepidopterans against predators and are biosynthetic precursors of male sex pheromones. The investigation of PAs in many species of wild-caught adults of Ithomiinae showed lycopsamine (1) [(7R)-OH, (2'S)-OH, (3'S)-OH] as the main alkaloid. In incorporation experiments, PA-free (freshly emerged) adults of the ithomiineMechanitis polymnia were fed seven PAs: lycopsamine and four of its known natural stereoisomers-indicine (2) [(7R)-OH, (2'R)-OH, (3'S)-OH], intermedine (3) [(7R)-OH, (2'S)-OH, (3'R)-OH], rinderine (4) [(7S)-OH, (2'S)-OH, (3'R)-OH], and echinatine (5) [(7S)-OH, (2'S)-OH, (3'S)-OH], and two PAs without the 7-OH: supinine (6) [(2'S)-OH, (3'R)-OH] and amabiline (7) [(2'S)-OH, (3'S)-OH]. Males epimerized PAs 3, 4, and 5 mainly to lycopsamine (1). Females fed these same three PAs changed a smaller proportion to lycopsamine; their lesser capacity to modify PAs corresponds to their normal acquisition of already transformed PAs from males during mating rather than through visits of adults to plant sources of PAs. The alkaloids1 and2, both 7R and 3'S, were incorporated without or with minimum change by males and females. Feeding experiments with6 and7 (males only) showed an inversion at the 3' center of6 and no change in7. The inversion from 7S to 7R (probably via oxyreduction) may be closely related to the evolution of acquisition of PAs by butterflies and moths. Two hypotheses are discussed: (1) The ancestral butterflies are probably adapted to tolerate, assimilate, and use (7R)-PAs (most common in plants; all widespread 1,2-unsaturated macrocyclic PA diesters show this configuration). The development of (7R)-PA receptors in the butterflies could lead to a specialization on this configuration in two ways: to help find PA plants and to utilize these components in sexual chemical communication. A later appearance of (7

  14. Complete 1H NMR assignments of pyrrolizidine alkaloids and a new eudesmanoid from Senecio polypodioides.

    Science.gov (United States)

    Villanueva-Cañongo, Claudia; Pérez-Hernández, Nury; Hernández-Carlos, Beatriz; Cedillo-Portugal, Ernestina; Joseph-Nathan, Pedro; Burgueño-Tapia, Eleuterio

    2014-05-01

    Chemical investigation of the aerial parts of Senecio polypodioides lead to the isolation of the new eudesmanoid 1β-angeloyloxyeudesm-7-ene-4β,9α-diol (1) and the known dirhamnosyl flavonoid lespidin (3), while from roots, the known 7β-angeloyloxy-1-methylene-8α-pyrrolizidine (5) and sarracine N-oxide (6), as well as the new neosarracine N-oxide (8), were obtained. The structure of 1 and 8 was elucidated by spectral means. Complete assignments of the (1)H NMR data for 5, 6, sarracine (7), and 8 were made using one-dimensional and two-dimensional NMR experiments and by application of the iterative full spin analysis of the PERCH NMR software. PMID:24574143

  15. Chemical Diversity Investigation of Hepatotoxic Pyrrolizidine Alkaloids in Qianliguang (Senecio scandens) and Related Species by UHPLC-QTOF-MS1

    Institute of Scientific and Technical Information of China (English)

    Lin Zhua; Na Li; Jian-Qing Ruan; Peter P. Fu; Zhong-Zhen Zhao; Ge Lina

    2015-01-01

    Objective: Qianliguang (Senecio scandens) is a common Chinese medicinal herb. Qianliguang-containing herbal proprietary products are registered as over-the-counter remedies in China and exported to Western countries. The presence of hepatotoxic pyrrolizidine alkaloids (PAs) has raised concerns about the safety of using Qianliguang and its products. The present study aims at investigation of different types of PAs present in Qianliguang collected from representative locations in China. Methods: In this study, a simple but specific UHPLC-QTOF-MS method for the determination of toxic PAs was developed, based on the characteristic fragment ions specific to different types of PAs. It was successfully applied for the identification and distinguishing of PAs present in Qianliguang and related Senecio species growing in different locations of China. Results: Significant diversity of the PA types and quantities were revealed among the samples tested. The estimated total amounts of toxic PAs in three of the samples exceed the toxic limits of PA intake restricted by WHO, demonstrating the timely and highly demand for regulating both types and quantities of PAs present in Qianliguang. Conclusions: This study provides the methodology for simultaneous identification and quantification of PAs present in herbs without requiring corresponding standards, which could be further used for more systematic investigations of the PA distribution in Qianliguang and other PA-containing herbs.

  16. Pyrrolizidine and tropane alkaloids in teas and the herbal teas peppermint, rooibos and chamomile in the Israeli market.

    Science.gov (United States)

    Shimshoni, Jakob Avi; Duebecke, Arne; Mulder, Patrick P J; Cuneah, Olga; Barel, Shimon

    2015-01-01

    Dehydro pyrrolizidine alkaloids (dehydro PAs) are carcinogenic phytotoxins prevalent in the Boraginaceae, Asteraceae and Fabaceae families. Dehydro PAs enter the food and feed chain by co-harvesting of crops intended for human and animal consumption as well as by carry-over into animal-based products such as milk, eggs and honey. Recently the occurrence of dehydro PAs in teas and herbal teas has gained increasing attention from the EU, due to the high levels of dehydro PAs found in commercially available teas and herbal teas in Germany and Switzerland. Furthermore, several tropane alkaloids (TAs, e.g. scopolamine and hyoscyamine) intoxications due to the consumption of contaminated herbal teas were reported in the literature. The aim of the present study was to determine the dehydro PAs and TAs levels in 70 pre-packed teabags of herbal and non-herbal tea types sold in supermarkets in Israel. Chamomile, peppermint and rooibos teas contained high dehydro PAs levels in almost all samples analysed. Lower amounts were detected in black and green teas, while no dehydro PAs were found in fennel and melissa herbal teas. Total dehydro PAs concentrations in chamomile, peppermint and rooibos teas ranged from 20 to 1729 μg/kg. Except for black tea containing only mono-ester retrorsine-type dehydro PAs, all other teas and herbal teas showed mixed patterns of dehydro PA ester types, indicating a contamination by various weed species during harvesting and/or production. The TA levels per teabag were below the recommended acute reference dose; however, the positive findings of TAs in all peppermint tea samples warrant a more extensive survey. The partially high levels of dehydro PAs found in teas and herbal teas present an urgent warning letter to the regulatory authorities to perform routine quality control analysis and implement maximum residual levels for dehydro PAs. PMID:26365752

  17. Pyrrolizidine alkaloids: Potential role in the etiology of cancers, pulmonary hypertension, congenital anomalies, and liver disease

    Science.gov (United States)

    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...

  18. Metabolism of toxic pyrrolizidine alkaloids from tansy ragwort (Senecio jacobaea) in ovine ruminal fluid under anaerobic conditions.

    Science.gov (United States)

    Craig, A M; Latham, C J; Blythe, L L; Schmotzer, W B; O'Connor, O A

    1992-01-01

    The ability of ovine ruminal fluid to metabolize pyrrolizidine alkaloid (PA) from Senecio jacobaea under anaerobic conditions was evaluated. Four fistulated sheep fed PA served as individual sources of ruminal fluid, which was incubated in a defined minimal salts medium under two different anaerobic conditions, denitrifying and methanogenic. Anaerobic cultures amended with ovine ruminal fluids (20%), PA (100 micrograms/ml), and a defined minimal salts medium were monitored for a period of several days. These cultures revealed that while PA was not depleted in sterile, autoclaved controls or under denitrifying conditions, it was metabolized during periods of active methanogenesis under methanogenic conditions. In addition, samples of ruminal fluid were separated by differential centrifugation under anaerobic conditions, and the resultant supernatants were tested for their ability to metabolize PA as compared with those of the respective uncentrifuged control fluids. Uncentrifuged controls exhibited a PA depletion rate of -4.04 +/- 0.17 micrograms of PA per ml per h. Supernatants 1 (centrifuged at 41 x g for 2 min), 2 (centrifuged at 166 x g for 5 min), and 3 (centrifuged at 1,500 x g for 10 min) exhibited significantly slower depletion rates, with slopes of data representing -1.64 +/- 0.16, -1.44 +/- 0.16, and -1.48 +/- 0.16 micrograms of PA metabolized per ml per h, respectively, demonstrating no statistically significant difference among the supernatant cultures. Microscopic evaluations revealed that protozoa were present in the control whole ruminal fluid and to a lesser extent in supernatant 1, while supernatants 2 and 3 contained only bacteria.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:1444382

  19. A rapid and highly specific method to evaluate the presence of pyrrolizidine alkaloids in Borago officinalis seed oil.

    Science.gov (United States)

    Vacillotto, Giulio; Favretto, Donata; Seraglia, Roberta; Pagiotti, Rita; Traldi, Pietro; Mattoli, Luisa

    2013-10-01

    Pyrrolizidine alkaloids (PAs) are complex molecules, present in plants as free bases and N-oxides. They are known for their hepatotoxicity, and consequently there is a health risk associated with the use of medicinal herbs that contain PAs. Unfortunately, there is no international regulation of PAs in foods, unlike those for herbs and medicines: in particular, for herbal preparation or herbal extracts, the total PA content must not exceed 1 µg/kg or 1 µg/l, respectively. Borago officinalis seed oil is a source of γ-linolenic acid, and its use is increased in both pharmaceutical and health food industries. Even if studies based on gas chromatography and TLC methods showed that PAs are not co-extracted with oil, the development of a rapid and sensitive method able to evaluate the presence of PAs in commercially available products is surely of interest. The presence of PAs in a commercially available Borago officinalis seed oil was tested either in the oil sample diluted with tetrahydrofuran/methanol (MeOH)/H2 O (85/10/5 v:v:v) or after extraction with MeOH/H2 O (50/50 v:v) solution The samples were analysed by electrospray ionization in positive ion mode and in high mass resolution (60,000) conditions. In both cases to evaluate the effectiveness of the method, spiking experiments were performed adding known amount of two PA standards to the borage seed oil. A limit of detection in the order of 200 ppt was determined for these two compounds, strongly analogous to Borago officinalis seed oil PAs. Consequently, if present, PAs level in Borago officinalis seed oil must lower than 200 ppt. PMID:24130010

  20. Modulation of gastrin and epidermal growth factor by pyrrolizidine alkaloids obtained from Senecio brasiliensis in acute and chronic induced gastric ulcers.

    Science.gov (United States)

    Toma, Walber; Trigo, José Roberto; Bensuaski de Paula, Ana Cláudia; Monteiro Souza Brito, Alba Regina

    2004-05-01

    We investigated the antiulcerogenic activity of pyrrolizidine alkaloids (PAs) integerrimine, retrorsine, senecionine, usaramine and seneciplhylline, an alkaloidal extract obtained from Senecio brasiliensis. The PA extract demonstrated significantly activity in both, acute and chronic gastric ulcers on rats. The effects of PA extract were dose dependent. The mechanisms implicated on this activity were evaluated by determination of gastrin plasma levels in rats subjected to the acute treatment with PA extract and by expression of mRNA of Epidermal Growth Factor (EGF) after chronic treatment with this extract. The results showed that the PA extract increased both the levels of gastrin and the expression of EGF on these animals. Moreover, the histological examinations showed a reduction of exfoliation of superficial cells, hemorrhages and blood cell infiltration. We concluded that the PAs showed an important and qualitative antiulcerogenic activity mediated by increase in gastrin secretion and mRNA expression of EGF. PMID:15213731

  1. Detection of pyrrolizidine alkaloids using flow analysis with both acidic potassium permanganate and tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence

    International Nuclear Information System (INIS)

    For the first time, analytically useful chemiluminescence was elicited from the reactions of the pyrrolizidine alkaloids. Heliotrine, retronecine, supinine, monocrotaline and echinatine N-oxide yielded chemiluminescence upon reaction with tris(2,2'-bipyridyl)ruthenium(II) whilst lasiocarpine, its N-oxide and supinine elicited light upon reaction with acidic potassium permanganate. Detection limits for heliotrine were 1.25 x 10-7 M and 9 x 10-9 M for tris(2,2'-bipyridyl)ruthenium(III) perchlorate with flow injection analysis (FIA) and the silica-immobilised reagent (4-[4-(dichloromethylsilanyl)-butyl]-4'-methyl-2,2'-bipyridine)bis (2,2'-bipyridyl)ruthenium(II) with sequential injection analysis (SIA), respectively. Lasiocarpine was detectable at 1.4 x 10-7 M using acidic potassium permanganate with FIA. Additionally, the silica-immobilised reagent was optimised with respect to the oxidant (ammonium ceric nitrate) concentration and the aspiration times which afforded a detection limit for codeine of 5 x 10-10 M using SIA

  2. Cell-Specific Expression of Homospermidine Synthase, the Entry Enzyme of the Pyrrolizidine Alkaloid Pathway in Senecio vernalis, in Comparison with Its Ancestor, Deoxyhypusine Synthase1

    Science.gov (United States)

    Moll, Stefanie; Anke, Sven; Kahmann, Uwe; Hänsch, Robert; Hartmann, Thomas; Ober, Dietrich

    2002-01-01

    Pyrrolizidine alkaloids (PAs) are constitutive plant defense compounds with a sporadic taxonomic occurrence. The first committed step in PA biosynthesis is catalyzed by homospermidine synthase (HSS). Recent evidence confirmed that HSS evolved by gene duplication from deoxyhypusine synthase (DHS), an enzyme involved in the posttranslational activation of the eukaryotic translation initiation factor 5A. To better understand the evolutionary relationship between these two enzymes, which are involved in completely different biological processes, we studied their tissue-specific expression. RNA-blot analysis, reverse transcriptase-PCR, and immunolocalization techniques demonstrated that DHS is constitutively expressed in shoots and roots of Senecio vernalis (Asteraceae), whereas HSS expression is root specific and restricted to distinct groups of endodermis and neighboring cortex cells located opposite to the phloem. All efforts to detect DHS by immunolocalization failed, but studies with promoter-β-glucuronidase fusions confirmed a general expression pattern, at least in young seedlings of tobacco (Nicotiana tabacum). The expression pattern for HSS differs completely from its ancestor DHS due to the adaptation of HSS to the specific requirements of PA biosynthesis. PMID:12226485

  3. Multi-analyte high performance liquid chromatography coupled to high resolution tandem mass spectrometry method for control of pesticide residues, mycotoxins, and pyrrolizidine alkaloids.

    Science.gov (United States)

    Dzuman, Zbynek; Zachariasova, Milena; Veprikova, Zdenka; Godula, Michal; Hajslova, Jana

    2015-03-10

    A new reliable and highly sensitive method based on high performance liquid chromatographic (HPLC) separation and high resolution tandem mass spectrometric detection (HRMS/MS) has been developed and validated for determination of 323 pesticide residues, 55 mycotoxins, and 11 plant toxins represented by pyrrolizidine alkaloids. The method was validated for three matrices, leek, wheat, and tea differing in nature/amount of co-extracts that may cause various matrix effects. For target analytes isolation, optimized QuEChERS-based (quick, easy, cheap, effective, rugged, and safe) extraction procedure was employed. Spectral HRMS/MS library has been established providing an entire spectrum of fragment ions for each analyte, which allows unbiased identification and confirmation of target compounds. The limits of quantification (LOQs) of target analytes were below 10 μg kg(-1) for 82%, 81%, and 61% for matrices leek, wheat, and tea, respectively. Recoveries were in the acceptable range (70-120%) according to SANCO/12571/2013 for most of target analytes, except for highly polar 'masked' mycotoxin deoxynivalenol-3-glucoside with recoveries 35%, 47%, and 42% for matrices leek, wheat, and tea, respectively. The linearities of calibration curves expressed as coefficients of determination were in the range of 0.9661-1.000, and repeatabilities expressed as relative standard deviations (RSDs) at LOQs lied in the range of 0.25-13.51%. The trueness of the method was verified using several certified reference materials (CRMs) and proficiency test samples.

  4. An Outbreak of Hepatic Veno-Occlusive Disease in Western Afghanistan Associated with Exposure to Wheat Flour Contaminated with Pyrrolizidine Alkaloids

    International Nuclear Information System (INIS)

    Pyrrolizidine alkaloids (PAs) are known to cause hepatic veno-occlusive disease (VOD). Outbreaks have occurred in Western Afghanistan since 1974, the latest in February 2008. We conducted an outbreak investigation using a case-control design. Sixty-seven cases of VOD were compared with 199 community controls. Consumption of bread was strongly associated with disease (adjusted odds ratio: 35.8 [95%CI: 7.6 168.2]). Toxic doses of PA were found in plant extracts and in samples of wheat flour taken from the study area. Compared to wheat flour there was 1000 times less PA in milk and whey and in water samples the PA content was zero. Although direct analysis was not possible, contaminated wheat flour used to make bread was the likely source of PA causing the outbreak. Eating a more varied diet including meat and fruit may be protective. Prevention and control measures will rely on community awareness and agricultural interventions to ensure safety of the food supply.

  5. Comparison of the anti-inflammatory active constituents and hepatotoxic pyrrolizidine alkaloids in two Senecio plants and their preparations by LC-UV and LC-MS.

    Science.gov (United States)

    Chen, Pinghong; Wang, Yi; Chen, Lulin; Jiang, Wei; Niu, Yan; Shao, Qing; Gao, Lu; Zhao, Quancheng; Yan, Licheng; Wang, Shufang

    2015-11-10

    Two Senecio plants, Senecio cannabifolius Less. and its variety S. cannabifolius Less. var. integrifolius (Kiodz.) Kidam., were both used as the raw material of Feining granule, a traditional Chinese medicine product for treating respiratory diseases. In this study, the chemical profiles of these two plants were investigated and compared by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR). A total number of 83 constituents, including 55 organic acids, 11 flavonoids, 4 alkaloids, 3 terpenes and 10 other types of compounds, were characterized. The results indicated that the levels of most flavonoids were higher in S. cannabifolius than in S. cannabifolius var. integrifolius, however, the levels of hepatotoxic pyrrolizidine alkaloids (PAs) were higher in S. cannabifolius var. integrifolius than in S. cannabifolius. Fifteen constituents were evaluated on lipopolysaccharides (LPS) induced RAW 264.7 cells, and eleven of them showed inhibition effect against nitric oxide (NO) production. Finally, the levels of ten major constituents (including seven anti-inflammatory active ones) and two PAs in Feining granule from two Senecio plants were determined and compared by the LC-UV and LC-MS methods, respectively. It was found that one organic acid (homogentisic acid) and two PAs (seneciphylline and senecionine) had higher contents in the preparation of S. cannabifolius var. integrifolius than in that of S. cannabifolius, however, the situations were inverse for the levels of four organic acids and flavonoids (chlorogenic acid, hyperoside, isoquercitrin, and isochlorogenic acid B). Based on the above results, S. cannabifolius might be a better raw material for Feining granule than S. cannabifolius var. integrifolius, because it contained more anti-inflammatory constituents and less hepatotoxic PAs than the latter. However, more pharmacological evaluations should be carried out to support the selection. The results in this study were helpful

  6. Involvement of Bcl-xL degradation and mitochondrial-mediated apoptotic pathway in pyrrolizidine alkaloids-induced apoptosis in hepatocytes

    International Nuclear Information System (INIS)

    Pyrrolizidine alkaloids (PAs) are natural hepatotoxins with worldwide distribution in more than 6000 high plants including medicinal herbs or teas. The aim of this study is to investigate the signal pathway involved in PAs-induced hepatotoxicity. Our results showed that clivorine, isolated from Ligularia hodgsonii Hook, decreased cell viability and induced apoptosis in L-02 cells and mouse hepatocytes. Western-blot results showed that clivorine induced caspase-3/-9 activation, mitochondrial release of cytochrome c and decreased anti-apoptotic Bcl-xL in a time (8-48 h)- and concentration (1-100 μM)-dependent manner. Furthermore, inhibitors of pan-caspase, caspase-3 and caspase-9 significantly inhibited clivorine-induced apoptosis and rescued clivorine-decreased cell viability. Polyubiquitination of Bcl-xL was detected after incubation with 100 μM clivorine for 40 h in the presence of proteasome specific inhibitor MG132, indicating possible degradation of Bcl-xL protein. Furthermore, pretreatment with MG132 or calpain inhibitor I for 2 h significantly enhanced clivorine-decreased Bcl-xL level and cell viability. All the other tested PAs such as senecionine, isoline and monocrotaline decreased mouse hepatocytes viability in a concentration-dependent manner. Clivorine (10 μM) induced caspase-3 activation and decreased Bcl-xL was also confirmed in mouse hepatocytes. Meanwhile, another PA senecionine isolated from Senecio vulgaris L also induced apoptosis, caspase-3 activation and decreased Bcl-xL in mouse hepatocytes. In conclusion, our results suggest that PAs may share the same hepatotoxic signal pathway, which involves degradation of Bcl-xL protein and thus leading to the activation of mitochondrial-mediated apoptotic pathway

  7. Structural screening by multiple reaction monitoring as a new approach for tandem mass spectrometry: presented for the determination of pyrrolizidine alkaloids in plants.

    Science.gov (United States)

    These, Anja; Bodi, Dorina; Ronczka, Stefan; Lahrssen-Wiederholt, Monika; Preiss-Weigert, Angelika

    2013-11-01

    In tandem mass spectrometry the multiple reaction monitoring (MRM) mode is normally used for targeted analysis but this mode also has the potential to screen for structural similarities of analytes. On the basis of the fact that in general similar molecular structures result in similar fragments or losses of neutrals, this approach was used for pyrrolizidine alkaloid (PA) screening but could also be easily adapted to screen for other compound classes. PA are plant toxins of which several hundred individual compounds have been identified. Our MRM screening approach uses the structural relation and similar core structure of all PA which results in a common and thus predictable mass spectrometric fragmentation behaviour. On this basis a method was developed which screens for PA structures by MRM transitions and allows the detection of each individual PA down to a low microgram per kilogram concentration range. The approach was applied to investigate plants from the families of Asteraceae (several species of Senecio and Eupatorium), Boraginaceae (Echium, Cynoglossum, Borago and Anchusa officinalis as well as Heliotropium europaeum) and Fabaceae (Crotalaria incana) for a complete qualitative and quantitative PA characterisation. All analytes that were detected as possible PA by MRM screening were further investigated by recording product ion spectra. Analytes which exhibited a typical PA fragmentation pattern were either confirmed as PA or otherwise deleted as false positive signals (false positive rate was below 10 %). Sum formulas of confirmed PA were determined by additional measurements applying high resolution mass spectrometry. In that way 121 unknown PA were identified and for the first time complete PA profiles of different PA plants were delivered. PMID:24114465

  8. Pyrrolizidine alkaloids pyrrolams A-D: A survey of synthetic efforts, biological activity, and studies on their stability

    Digital Repository Service at National Institute of Oceanography (India)

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

    synthesis of pyrrolam A along with other members of this class of alkaloids. 18b The author’s approach was based on cyclization of N-methoxy-N-methyl amide 14 to dione 15 via N-acetyl anion- cyclization reaction. The requisite N-methoxy-N-methyl amide 14... was prepared from N-acetyl prolinate via a mixed anhydride protocol. Reduction of keto functionality of 15 with NaBH 4 furnished alcohol 16, which was subjected to mesylation (MsCl) followed by treatment with triethylamine in refluxing CHCl 3 afforded (S...

  9. 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. PMID:26177929

  10. Effects of root herbivory on pyrrolizidine alkaloid content and aboveground plant-herbivore-parasitoid interactions in Jacobaea vulgaris

    NARCIS (Netherlands)

    Kostenko, O.; Mulder, P.P.J.; Bezemer, T.M.

    2013-01-01

    The importance of root herbivory is increasingly recognized in ecological studies, and the effects of root herbivory on plant growth, chemistry, and performance of aboveground herbivores have been relatively well studied. However, how belowground herbivory by root feeding insects affects aboveground

  11. Effects of Root Herbivory on Pyrrolizidine Alkaloid Content and Aboveground Plant-Herbivore-Parasitoid Interactions in Jacobaea Vulgaris

    NARCIS (Netherlands)

    Kostenko, O.; Mulder, P.P.J.; Bezemer, T.M.

    2013-01-01

    The importance of root herbivory is increasingly recognized in ecological studies, and the effects of root herbivory on plant growth, chemistry, and performance of aboveground herbivores have been relatively well studied. However, how belowground herbivory by root feeding insects affects aboveground

  12. Effects of root herbivory on pyrrolizidine alkaloid content and aboveground plant-herbivore-parasitoid interactions in Jacobaea vulgaris

    OpenAIRE

    O. Kostenko; Mulder, P.P.J.; Bezemer, T.M.

    2013-01-01

    The importance of root herbivory is increasingly recognized in ecological studies, and the effects of root herbivory on plant growth, chemistry, and performance of aboveground herbivores have been relatively well studied. However, how belowground herbivory by root feeding insects affects aboveground parasitoid development is largely unknown. In this study, we examined the effects of root herbivory by wireworms (Agriotes lineatus) on the expression of primary and secondary compounds in the lea...

  13. Two new pyrrolizidine alkaloids from Senecio nemorensis.

    Science.gov (United States)

    Shi, Bao-Jun; Xiong, Ai-Zhen; Zheng, Shan-Song; Chou, Gui-Xin; Wang, Zheng-Tao

    2010-12-01

    Two new compounds, including petasinoside A and chloridate-[N-chloromethyl-hectorine], were isolated from Senecio nemorensis. The structures of these compounds were elucidated by spectroscopic methods including 1D and 2D NMR experiments. PMID:21128163

  14. 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

  15. Ether bridge formation in loline alkaloid biosynthesis

    OpenAIRE

    Pan, Juan; Bhardwaj, Minakshi; Faulkner, Jerome R.; Nagabhyru, Padmaja; Charlton, Nikki D.; Higashi, Richard M.; Miller, Anne-Frances; Young, Carolyn A; Grossman, Robert B.; Schardl, Christopher L

    2013-01-01

    Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lolO, resulting in the accumulation of a novel alkaloid identified as exo-1-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes...

  16. Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides.

    Science.gov (United States)

    Dembitsky, Valery M

    2005-11-01

    This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided into several groups, including: acridone; aporphine; benzoxazinoid; ergot; indole; enediyne alkaloidal antibiotics; glycosidic lupine alkaloids; piperidine, pyridine, pyrrolidine, and pyrrolizidine alkaloid glycosides; glycosidic quinoline and isoquinoline alkaloids; steroidal glycoalkaloids; and miscellaneous alkaloid glycosides. PMID:16459921

  17. Reaction of dehydropyrrolizidine alkaloids with valine and hemoglobin.

    Science.gov (United States)

    Zhao, Yuewei; Wang, Shuguang; Xia, Qingsu; Gamboa da Costa, Gonçalo; Doerge, Daniel R; Cai, Lining; Fu, Peter P

    2014-10-20

    Pyrrolizidine alkaloid-containing plants are probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids exert toxicity through metabolism to dehydropyrrolizidine alkaloids that bind to cellular protein and DNA, leading to hepatotoxicity, genotoxicity, and tumorigenicity. To date, it is not clear how dehydropyrrolizidine alkaloids bind to cellular constituents, including amino acids and proteins, resulting in toxicity. Metabolism of carcinogenic monocrotaline, riddelliine, and heliotrine produces dehydromonocrotaline, dehyroriddelliine, and dehydroheliotrine, respectively, as primary reactive metabolites. In this study, we report that reaction of dehydromonocrotaline with valine generated four highly unstable 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived valine (DHP-valine) adducts. For structural elucidation, DHP-valine adducts were derivatized with phenyl isothiocyanate (PITC) to DHP-valine-PITC products. After HPLC separation, their structures were characterized by mass spectrometry, UV-visible spectrophotometry, (1)H NMR, and (1)H-(1)H COSY NMR spectral analysis. Two DHP-valine-PITC adducts, designated as DHP-valine-PITC-1 and DHP-valine-PITC-3, had the amino group of valine linked to the C7 position of the necine base, and the other two DHP-valine-PITC products, DHP-valine-PITC-2 and DHP-valine-PITC-4, linked to the C9 position of the necine base. DHP-valine-PITC-1 was interconvertible with DHP-valine-PITC-3, and DHP-valine-PITC-2 was interconvertible with DHP-valine-PITC-4. Reaction of dehydroriddelliine and dehydroheliotrine with valine provided similar results. However, reaction of valine and dehydroretronecine (DHR) under similar experimental conditions did not produce DHP-valine adducts. Reaction of dehydromonocrotaline with rat hemoglobin followed by derivatization with PITC also generated the same four DHP-valine-PITC adducts. This represents the first full structural elucidation of

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

    Science.gov (United States)

    Diaz, Gonzalo J

    2015-12-11

    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.

  19. 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.

  20. An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides

    Science.gov (United States)

    Plants containing dehydro-pyrrolizidine alkaloids (PAs) can be found throughout the world and their invasive, weedy nature often results in PA contamination of feed and food. Other PA-containing plants may be purposefully or accidentally included in food or herbal preparations. Poisoning can be acu...

  1. The pyrrolidinoindoline alkaloid Psm2 inhibits platelet aggregation and thrombus formation by affecting PI3K/Akt signaling

    Science.gov (United States)

    Su, Xing-li; Su, Wen; Wang, Ying; Wang, Yue-hu; Ming, Xin; Kong, Yi

    2016-01-01

    Aim: Psm2, one of the pyrrolidinoindoline alkaloids isolated from whole Selaginella moellendorffii plants, has shown a potent antiplatelet activity. In this study, we further evaluated the antiplatelet effects of Psm2, and elucidated the underlying mechanisms. Methods: Human platelet aggregation in vitro and rat platelet aggregation ex vivo were investigated. Agonist-induced platelet aggregation was measured using a light transmission aggregometer. The antithrombotic effects of Psm2 were evaluated in arteriovenous shunt thrombosis model in rats. To elucidate the mechanisms underlying the antiplatelet activity of Psm2, ELISAs, Western blotting and molecular docking were performed. The bleeding risk of Psm2 administration was assessed in a mouse tail cutting model, and the cytotoxicity of Psm2 was measured with MTT assay in EA.hy926 cells. Results: Psm2 dose-dependently inhibited human platelet aggregation induced by ADP, U4619, thrombin and collagen with IC50 values of 0.64, 0.37, 0.35 and 0.87 mg/mL, respectively. Psm2 (1, 3, 10 mg/kg) administered to rats significantly inhibited platelet aggregation ex vivo induced by ADP. Psm2 (1, 3, 10 mg/mL, iv) administered to rats with the A–V shunt dose-dependently decreased the thrombus formation. Psm2 inhibited platelet adhesion to fibrinogen and collagen with IC50 values of 84.5 and 96.5 mg/mL, respectively, but did not affect the binding of fibrinogen to GPIIb/IIIa. Furthermore, Psm2 inhibited AktSer473 phosphorylation, but did not affect MAPK signaling and Src kinase activation. Molecular docking showed that Psm2 bound to phosphatidylinositol 3-kinase β (PI3Kβ) with a binding free energy of −13.265 kcal/mol. In addition, Psm2 did not cause toxicity in EA.hy926 cells and produced only slight bleeding in a mouse tail cutting model. Conclusion: Psm2 inhibits platelet aggregation and thrombus formation by affecting PI3K/Akt signaling. Psm2 may be a lead compound or drug candidate that could be developed for the

  2. Vinca Alkaloids

    Directory of Open Access Journals (Sweden)

    Maryam Moudi

    2013-01-01

    Full Text Available Vinca alkaloids are a subset of drugs obtained from the Madagascar periwinkle plant. They are naturally extracted from the pink periwinkle plant, Catharanthus roseus G. Don and have a hypoglycemic as well as cytotoxic effects. They have been used to treat diabetes, high blood pressure and have been used as disinfectants. The vinca alkaloids are also important for being cancer fighters. There are four major vinca alkaloids in clinical use: Vinblastine (VBL, vinorelbine (VRL, vincristine (VCR and vindesine (VDS. VCR, VBL and VRL have been approved for use in the United States. Vinflunine is also a new synthetic vinca alkaloid, which has been approved in Europe for the treatment of second-line transitional cell carcinoma of the urothelium is being developed for other malignancies. Vinca alkaloids are the second-most-used class of cancer drugs and will stay among the original cancer therapies. Different researches and studies for new vinca alkaloid applications will be carried out in this regard.

  3. Production of imidazole alkaloids in cell cultures of jaborandi as affected by the medium pH.

    Science.gov (United States)

    Andreazza, N L; Abreu, I N; Sawaya, A C H F; Eberlin, M N; Mazzafera, P

    2009-04-01

    The effect of pH (from 4.8 to 9.8) on the production of pilosine and pilocarpine and on their partition between cell and medium was studied in two lineages (P and PP) of Pilocarpus microphyllus cell suspension cultures. Highest mass accumulation was observed at high pHs and both lineages produced pilocarpine while only lineage PP produced pilosine. Both alkaloids were released in the medium but higher accumulation occurred in the cells. The highest production of pilocarpine was at pH 8.8-9.8 in both cell lineages. Other imidazole alkaloids were also identified in both lineages. At all pHs tested, the pH in the media cultures tended to stabilize around 6 after 10-15 days of cultivation. NO3(-) and NH4+ variation in the media might partially explain the pH stabilization. PMID:19066732

  4. Induction of micronuclei by alkaloids extracted from Senecio brasiliensis and stored for 23 years.

    Science.gov (United States)

    Santos-Mello, R; Deimlimg, L I; Lauer Júnior, C M; Almeida, A

    2002-04-26

    In the present study, we report the results of an investigation on pyrrolizidine alkaloids extracted from Senecio brasiliensis (Sprengel) Less., which were stored for more than 23 years under variable conditions of temperature and humidity and exposed to light. Both the crude alkaloid (integerrimine+retrorsine+impurities) and pure integerrimine conserved the ability to induce acute toxicity in mice, leading to the death of the animals in less than 24h. The alkaloids also conserved the potential to induce significant increases in micronucleus frequencies in polychromatic erythrocytes of mouse bone marrow compared to the negative control. The administration of alkaloids to lymphocyte cultures blocked with cytochalasin-B showed no significant increase in micronucleus frequency in binucleated cells, probably due to the lack of a metabolic activation mechanism. However, an antimitotic effect was observed. PMID:11943607

  5. Temperature and Plant Genotype Alter Alkaloid Concentrations in Ryegrass Infected with an Epichloë Endophyte and This Affects an Insect Herbivore

    Science.gov (United States)

    Hennessy, Louise M.; Popay, Alison J.; Finch, Sarah C.; Clearwater, Michael J.; Cave, Vanessa M.

    2016-01-01

    Asexual Epichloë endophytes colonize agricultural forage grasses in a relationship which is mutually beneficial and provides the host plant with protection against herbivorous insects. The endophyte strain AR37 (Epichloë festucae var. lolii) produces epoxy-janthitrem alkaloids and is the only endophyte known to provide ryegrass with resistance against porina larvae (Wiseana cervinata (Walker)), a major pasture pest in cooler areas of New Zealand. This study examined the effect of temperature on concentrations of epoxy-janthitrems in AR37-infected ryegrass and determined how the resulting variations in concentration affected consumption, growth and survival of porina larvae. Twenty replicate pairs of perennial (Lolium perenne L.) and Italian ryegrass (L. multiflorum Lam.) plants with and without endophyte were prepared by cloning, with one of each pair grown at either high (20°C) or low (7°C) temperature. After 10 weeks, herbage on each plant was harvested, divided into leaf and pseudostem, then freeze dried and ground. Leaf and pseudostem material was then incorporated separately into semi-synthetic diets which were fed to porina larvae in a bioassay over 3 weeks. Epoxy-janthitrem concentrations within the plant materials and the semi-synthetic diets were analyzed by high performance liquid chromatography. AR37-infected ryegrass grown at high temperature contained high in planta concentrations of epoxy-janthitrem (30.6 μg/g in leaves and 83.9 μg/g in pseudostems) that had a strong anti-feedant effect on porina larvae when incorporated into their diets, reducing their survival by 25–42% on pseudostems. In comparison, in planta epoxy-janthitrem concentrations in AR37-infected ryegrass grown at low temperature were very low (0.67 μg/g in leaves and 7.4 μg/g in pseudostems) resulting in a small anti-feedant effect in perennial but not in Italian ryegrass. Although alkaloid concentrations were greatly reduced by low temperature this reduction did not occur

  6. 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.

  7. Pyrrolizidine alkaloid variation in Jacobaea hybrids : influence on resistance against generalist and specialist insect herbivores

    NARCIS (Netherlands)

    Cheng, Dandan

    2012-01-01

    Plants produce a vast array of secondary metabolites (SMs). Some hypotheses were put forward to explain the diversity of structurally related SMs within the framework of plant defense against herbivores:1) SMs could be Selectively Neutral; 2) SM diversity is a result of the “Arms Race” between plant

  8. Differences in effects of pyrrolizidine alkaloids on five generalist insect herbivore species

    NARCIS (Netherlands)

    Macel, M.; Bruinsma, M.; Dijkstra, S.M.; Ooijendijk, T.; Niemeyer, T.; Klinkhamer, P.G.L.

    2005-01-01

    The evolution of the diversity in plant secondary compounds is often thought to be driven by insect herbivores, although there is little empirical evidence for this assumption. To investigate whether generalist insect herbivores could play a role in the evolution of the diversity of related compound

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

    NARCIS (Netherlands)

    Carvalho, S.; Macel, M.; Schlerf, M.; Eghbali Moghaddam, F.; Mulder, P.P.J.; Skidmore, A.K.; Van der Putten, W.H.

    2013-01-01

    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 fir

  10. I. Cyclopeptide alkaloids; II. Phycocyanobilipeptides

    Energy Technology Data Exchange (ETDEWEB)

    Lagarias, J.C.

    1979-09-01

    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 cyclopeptide alkaloid, ceanothine B, bind monovalent (Li/sup +/) and divalent (Ca/sup + +/, Mg/sup + +/) cations. Seven cyclopeptide alkaloids, phencyclopeptines 1-7, have been found distributed among three forms of the shrub Ceanothus integerrimus. Chemical degradation, mass spectroscopy, and /sup 1/H NMR spectroscopy have established structures for these seven compounds, three of which have been previously reported. The utility of cyclopeptide alkaloid structure and the distribution for chemotaxonomic assignments is discussed. Field desorption mass spectroscopy has identified five phencyclopeptines in the crude alkaloidal extracts of Ceanothus sanguineus. A new paired-ion HPLC system for the separation of these alkaloids is discussed. Amino acid analysis, electron impact mass spectroscopy, and /sup 1/H NMR spectroscopy have established the structures of six phencyclopeptines including two isomeric compounds 5 and 6. The structure of 2 has not been previously reported. The smallest cyanogen bromide fragment derived from the ..beta..-subunit of Synechococcus sp 6301 C-phycocyanin, the blue heptapeptide 2, has been investigated by 360 MHz /sup 1/H NMR spectroscopy. The peptide portion, heptapeptide 3, was synthesized independently and used in comparative spectroscopic analysis.These studies have led to complete assignment of the structure of the peptide-linked phycocyanobilin and elucidation of the nature of the thioether chromophore-peptide linkage.

  11. Seasonal Change of Loline Alkaloids in Endophyte-lnfected Meadow Fescue

    Institute of Scientific and Technical Information of China (English)

    TONG De-wen; WANG Jin-yi; Brain Patchett; Ravi Gooneratne

    2006-01-01

    Lolines are a group of saturated pyrrolizidine alkaloids that possess broad bioactivity against a wide array of herbivorous insects. However, they do not exhibit toxicity to ruminants such as cattle and sheep. In order to study the direct and potential physiological effects on ruminants and the mechanism of insecticide/insectifuge, the distribution of loline alkaloids in endophyte-infected meadow fescue and the seasonal change of the distribution were analyzed. The crowns,roots and leaves of endophyte-infected meadow fescue at its four different growth periods, i.e., spring, summer, early autumn and late autumn, in New Zealand were colleted. After powdering, organic solvent extraction and purification by column chromatography, all loline alkaloid samples were analyzed by capillary gas chromatography with 4-phenylmorpholine (PM) as an internal standard. The analytic results showed that the loline contents in the roots, crowns and leaves of endophyte-infected meadow fescue vary with seasons. Even within the same season, the distribution of lolines in endophyte-infected meadow fescue varies. During summer, lolines mainly existed in the leaves and roots, but in early autumn, they are produced in the crowns. It was concluded that, lolines were mainly produced in the leaves and roots of endophyte-infected meadow fescue. In gas chromatographic analysis, N-formylloline, the major component of loline alkaloid in the plant, was employed to assay the alkaloids.

  12. Carcinogenic effects of riddelliine on P53 knockout mice

    Science.gov (United States)

    Riddelliine is a pyrrolizidine alkaloid found in Senecio riddellii and several other Senecio spp. Pyrrolizidine alkaloids are a group of over 600 toxins, found in more than 6,000 plants worldwide. As a result they are likely the most economically significant plant toxin in the world, affecting a wi...

  13. Alkaloids in Marine Algae

    OpenAIRE

    Ekrem Sezik; Aline Percot; Kasım Cemal Güven

    2010-01-01

    This paper presents the alkaloids found in green, brown and red marine algae. Algal chemistry has interested many researchers in order to develop new drugs, as algae include compounds with functional groups which are characteristic from this particular source. Among these compounds, alkaloids present special interest because of their pharmacological activities. Alkaloid chemistry has been widely studied in terrestrial plants, but the number of studies in algae is insignificant. In this review...

  14. Absolute configuration, stability, and interconversion of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine valine adducts and their phenylthiohydantoin derivatives

    OpenAIRE

    Xiao Jiang; Shuguang Wang; Yuewei Zhao; Qingsu Xia; Lining Cai; Xin Sun; Peter P. Fu

    2015-01-01

    Pyrrolizidine alkaloid-containing plants are widespread in the world and probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids require metabolic activation to form dehydropyrrolizidine alkaloids that bind to cellular proteins and DNA leading to hepatotoxicity, genotoxicity, and tumorigenicity. At present, it is not clear how dehydropyrrolizidine alkaloids bind to cellular amino acids and proteins to induced toxicity. We previously reporte...

  15. [Alkaloids of Annonaceae. XXIX. Alkaloids of Annona muricata].

    Science.gov (United States)

    Leboeuf, M; Legueut, C; Cavé, A; Desconclois, J F; Forgacs, P; Jacquemin, H

    1981-05-01

    From leaves, root - and stem - barks of Annona muricata L., seven isoquinoline alkaloids have been isolated: reticuline (main alkaloid), coclaurine, coreximine, atherosperminine, stepharine. Anomurine and anomuricine, two minor alkaloids, are new tetrahydrobenzylisoquinolines, with 5, 6, 7 substituted ring A. The phytochemical significance of these alkaloids is discussed.

  16. 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.

  17. 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...

  18. Occurrence of halogenated alkaloids.

    Science.gov (United States)

    Gribble, Gordon W

    2012-01-01

    Once considered to be isolation artifacts or chemical "mistakes" of nature, the number of naturally occurring organohalogen compounds has grown from a dozen in 1954 to >5000 today. Of these, at least 25% are halogenated alkaloids. This is not surprising since nitrogen-containing pyrroles, indoles, carbolines, tryptamines, tyrosines, and tyramines are excellent platforms for biohalogenation, particularly in the marine environment where both chloride and bromide are plentiful for biooxidation and subsequent incorporation into these electron-rich substrates. This review presents the occurrence of all halogenated alkaloids, with the exception of marine bromotyrosines where coverage begins where it left off in volume 61 of The Alkaloids. Whereas the biological activity of these extraordinary compounds is briefly cited for some examples, a future volume of The Alkaloids will present full coverage of this topic and will also include selected syntheses of halogenated alkaloids. Natural organohalogens of all types, especially marine and terrestrial halogenated alkaloids, comprise a rapidly expanding class of natural products, in many cases expressing powerful biological activity. This enormous proliferation has several origins: (1) a revitalization of natural product research in a search for new drugs, (2) improved compound characterization methods (multidimensional NMR, high-resolution mass spectrometry), (3) specific enzyme-based and other biological assays, (4) sophisticated collection methods (SCUBA and remote submersibles for deep ocean marine collections), (5) new separation and purification techniques (HPLC and countercurrent separation), (6) a greater appreciation of traditional folk medicine and ethobotany, and (7) marine bacteria and fungi as novel sources of natural products. Halogenated alkaloids are truly omnipresent in the environment. Indeed, one compound, Q1 (234), is ubiquitous in the marine food web and is found in the Inuit from their diet of whale

  19. Marine Indole Alkaloids

    Directory of Open Access Journals (Sweden)

    Natalie Netz

    2015-08-01

    Full Text Available Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed.

  20. Sarpagine and Related Alkaloids.

    Science.gov (United States)

    Namjoshi, Ojas A; Cook, James M

    2016-01-01

    The sarpagine-related macroline and ajmaline alkaloids share a common biosynthetic origin, and bear important structural similarities, as expected. These indole alkaloids are widely dispersed in 25 plant genera, principally in the family Apocynaceae. Very diverse and interesting biological properties have been reported for this group of natural products. Isolation of new sarpagine-related alkaloids and the asymmetric synthesis of these structurally complex molecules are of paramount importance to the synthetic and medicinal chemists. A total of 115 newly isolated sarpagine-related macroline and ajmaline alkaloids, along with their physicochemical properties have been included in this chapter. A general and efficient strategy for the synthesis of these monomeric alkaloids, as well as bisindoles, has been presented, which involves application of the asymmetric Pictet-Spengler reaction (>98% ee) as a key step because of the ease of scale up of the tetracyclic template. Also included in this chapter are the syntheses of the sarpagine-related alkaloids, published since 2000. PMID:26827883

  1. Analysis of Ergot Alkaloids

    Directory of Open Access Journals (Sweden)

    Colin Crews

    2015-06-01

    Full Text Available The principles and application of established and newer methods for the quantitative and semi-quantitative determination of ergot alkaloids in food, feed, plant materials and animal tissues are reviewed. The techniques of sampling, extraction, clean-up, detection, quantification and validation are described. The major procedures for ergot alkaloid analysis comprise liquid chromatography with tandem mass spectrometry (LC-MS/MS and liquid chromatography with fluorescence detection (LC-FLD. Other methods based on immunoassays are under development and variations of these and minor techniques are available for specific purposes.

  2. Simple Indolizidine and Quinolizidine Alkaloids.

    Science.gov (United States)

    Michael, Joseph P

    2016-01-01

    This review of simple indolizidine and quinolizidine alkaloids (i.e., those in which the parent bicyclic systems are in general not embedded in polycyclic arrays) is an update of the previous coverage in Volume 55 of this series (2001). The present survey covers the literature from mid-1999 to the end of 2013; and in addition to aspects of the isolation, characterization, and biological activity of the alkaloids, much emphasis is placed on their total synthesis. A brief introduction to the topic is followed by an overview of relevant alkaloids from fungal and microbial sources, among them slaframine, cyclizidine, Steptomyces metabolites, and the pantocins. The important iminosugar alkaloids lentiginosine, steviamine, swainsonine, castanospermine, and related hydroxyindolizidines are dealt with in the subsequent section. The fourth and fifth sections cover metabolites from terrestrial plants. Pertinent plant alkaloids bearing alkyl, functionalized alkyl or alkenyl substituents include dendroprimine, anibamine, simple alkaloids belonging to the genera Prosopis, Elaeocarpus, Lycopodium, and Poranthera, and bicyclic alkaloids of the lupin family. Plant alkaloids bearing aryl or heteroaryl substituents include ipalbidine and analogs, secophenanthroindolizidine and secophenanthroquinolizidine alkaloids (among them septicine, julandine, and analogs), ficuseptine, lasubines, and other simple quinolizidines of the Lythraceae, the simple furyl-substituted Nuphar alkaloids, and a mixed quinolizidine-quinazoline alkaloid. The penultimate section of the review deals with the sizable group of simple indolizidine and quinolizidine alkaloids isolated from, or detected in, ants, mites, and terrestrial amphibians, and includes an overview of the "dietary hypothesis" for the origin of the amphibian metabolites. The final section surveys relevant alkaloids from marine sources, and includes clathryimines and analogs, stellettamides, the clavepictines and pictamine, and bis

  3. Alkaloids from Galanthus nivalis.

    Science.gov (United States)

    Berkov, Strahil; Codina, Carles; Viladomat, Francesc; Bastida, Jaume

    2007-07-01

    Phytochemical studies on Galanthus nivalis of Bulgarian origin resulted in the isolation of five compounds: 11-O-(3'-hydroxybutanoyl)hamayne, 3,11-O-(3',3''-dihydroxybutanoyl)hamayne, 3-O-(2''-butenoyl)-11-O-(3'-hydroxybutanoyl)hamayne, 3,11,3''-O-(3',3'',3'''-trihydroxybutanoyl)hamayne, and 2-O-(3'-acetoxybutanoyl)lycorine, together with five known alkaloids: ungeremine, lycorine, tazettine, hamayne, and ismine. Their structures were determined by (1)H and (13)C NMR spectroscopy and two-dimensional (1)H-(1)H and (1)H-(13)C chemical shift correlation experiments.

  4. Biosynthesis of tylophora alkaloids

    International Nuclear Information System (INIS)

    Using labelled precursors, biosynthesis of the tylophora alkaloids, tylophorine, tylophorinidine and tylophorinide has been investigated in Tylophora asthmatica plants. The radioactive precursors, phenylalanine-2-14C, benzoic acid-1-14C, benzoic acid-ring 14C, acetate-2-14C, ornithine-5-14C, acetate-2-14C, ornithine-5-14C and cinnamic acid-2-14C 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.)

  5. Total Synthesis of Securinega Alkaloids

    Institute of Scientific and Technical Information of China (English)

    T. Honda

    2005-01-01

    @@ 1Introduction Naturally occurring Securinega alkaloids (1-4) (Fig. 1)[1], with their wide range of structural and stereochemical features, continue to provide challenging synthetic targets, since these alkaloids exhibit attractive biological activities. Securinine (1), isolated from Securinega suffruticosa [2], was structurally determined to contain an indolizidine skeleton with an azabicyclo[3.2.1 ]octane system together with an α, β-unsaturated γ-lactone ring. This alkaloid has been clinically used in Russia as a CNS stimulating drug[3], and has been shown to act as a stereospecific antagonist at the GABA binding site of the GABAA-receptor complex[4].Viroallosecurinine (2), a diastereoisomeric alkaloid of securinine, was also isolated from the leaves of Securinega virosa[5] as a cytotoxic alkaloid exhibiting a MIC of 0.48 μg/mL for Ps. aeruginosa and Staph.aureus[6]. This alkaloid is recognized to be bactericidal since the yields of MIC/MBC were less than 1[7].

  6. Influence of Some Heavy Metals on Growth, Alkaloid Content and Composition in Catharanthus roseus L.

    Science.gov (United States)

    Srivastava, N. K.; Srivastava, A. K.

    2010-01-01

    Shoot biomass production, alkaloid content and composition as influence by cadmium, manganese, nickel and lead at uniform dose of 5 mM were investigated in Catharanthus roseus plants grown in sand culture. Treatment with Mn, Ni, and Pb significantly enhanced total root alkaloid accumulation. Cd and Ni treatment resulted in two-fold where as Pb treatment resulted in three fold increase in serpentine content of roots. The non-significant affect on biomass suggests that plants can withstand metal stress at the level tested with positive affect on root alkaloid content. PMID:21969751

  7. Copper catalysed synthesis of indolylquinazolinone alkaloid bouchardatine

    Indian Academy of Sciences (India)

    Mayavan Viji; Rajagopal Nagarajan

    2014-07-01

    We describe the total synthesis of indolylquinazolinone alkaloid bouchardatine and some of the quinazolinone derivatives. The aerobic oxidation induced by copper(I) bromide, followed by Vilsmeier-Haack formylation gives the natural product bouchardatine alkaloid in good yield.

  8. Antimicrobial activity of benzylisoquinoline alkaloids.

    Science.gov (United States)

    Villar, A; Mares, M; Rios, J L; Canton, E; Gobernado, M

    1987-04-01

    The antimicrobial in vitro activity of 14 benzylisoquinoline alkaloids was investigated by agar diffusion and agar dilution methods against several genera of microorganisms that included Streptococcus, Staphylococcus, Bacillus, Lysteria, Escherichia, Salmonella, Klebsiella, Pseudomonas, Enterobacter, Serratia, Shigella, Mycobacterium and Candida. Anolobine was the most active compound against grampositive bacteria with MIC90 between 12 and 50 mg/l; less active were anonaine, lysicamine and liriodenine. All the alkaloids of the noraporphine and oxoaporphine groups, with the exception of isopiline, showed activity against Mycobacterium phlei (MIC 6-25 mg/l). Candida albicans ATCC26555 was inhibited by anonaine, nornantenine and xylopine (MIC 3-12 mg/l). None of the alkaloids tested had a significant activity against gramnegative rods. The action against susceptible microorganisms was bactericidal. PMID:3615557

  9. Alkaloids from Stems of Ervatamia yunnanensis (Ⅱ)

    Institute of Scientific and Technical Information of China (English)

    Shuang LIANG; Xin Gen LUO; Hai Sheng CHEN; Xiao Dong ZHANG; Mao HUANG; Wen Yong LIU

    2006-01-01

    Six indole alkaloids were isolated from the stems of Ervatamia yunnanensis. Among them, 10-hydroxy-19, 20-dihydroisositsirikine (Ⅰ) is new. The other five are known alkaloids,namely: matrine (Ⅱ), 19, 20-dihydroisositsuikine (Ⅲ), 19-s-voacangarine (Ⅳ), 11'-methoxyl- 19s-heyneanine (Ⅴ), conodurine (Ⅵ). The structural elucidation of the alkaloids was based on spectral means.

  10. Alkaloids from stems of Ervatamia yunnanensis

    Institute of Scientific and Technical Information of China (English)

    Xin Gen Luo; Hai Sheng Chen; Shuang Liang; Mao Huang; Wei Dong Xuan; Li Jin

    2007-01-01

    Six indole alkaloids were isolated from the stems of Ervatamia yunnanensis.Among them, yunnanensine (Ⅰ) is new.The other five are known alkaloids, namely: 19,20-E-vallesamine (Ⅱ), 19s-heyneanine (Ⅲ), ibogaine (Ⅳ), ibogamine (Ⅴ), coronaridine (Ⅵ).The structural elucidation of the alkaloids was based on spectral means.

  11. FIVE NEW NORDITERPENOID ALKALOIDS FROM ACONITUM SINOMONTANUM

    Institute of Scientific and Technical Information of China (English)

    FENG-PENG WANG; CHONG-SHENG PENG; XI-XIAN JIAN; DONG-LIN CHEN

    2001-01-01

    From the roots of A conitum sinomontanum, five new norditerpenoid alkaloids, sinomontanitines A (1) and B (2), sinomontanines A (3), B (4) and C (5), were isolated together with the known alkaloids lappaconitine (6) and ranaconitine (7), The structures of the new alkaloids were determined by spectral analysis.

  12. The alkaloid profiles of Lupinus sulphureus.

    Science.gov (United States)

    Cook, Daniel; Lee, Stephen T; Gardner, Dale R; Pfister, James A; Welch, Kevin D; Green, Benedict T; Davis, T Zane; Panter, Kip E

    2009-02-25

    Lupines are common plants on the rangelands in the western United States. Lupines contain alkaloids that can be toxic and teratogenic causing congenital birth defects (crooked calf disease). One such lupine, Lupinus sulphureus, occurs in parts of Oregon, Washington, and British Columbia. Specimens of L. sulphureus from field collections and herbaria were evaluated taxonomically and by chemical means. A total of seven distinct alkaloid profiles and the individual alkaloids associated with each profile were identified. Each alkaloid profile was unique in its geographical distribution and its potential risk to livestock. In conclusion, taxonomic classification is not sufficient to determine risk, as chemical characterization of the alkaloids must also be performed.

  13. Affectivity

    OpenAIRE

    Stenner, Paul; Greco, Monica

    2013-01-01

    The concept of affectivity has assumed central importance in much recent scholarship, and many in the social sciences and humanities now talk of an ‘affective turn’. The concept of affectivity at play in this ‘turn’ remains, however, somewhat vague and slippery. Starting with Silvan Tomkins’ influential theory of affect, this paper will explore the relevance of the general assumptions (or ‘utmost abstractions’) that inform thinking about affectivity. The technological and instrumentalist char...

  14. 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)

  15. Quaternary alkaloids of tinospora species.

    Science.gov (United States)

    Bisset, N G; Nwaiwu, J

    1983-08-01

    The occurrence of quaternary alkaloids in TINOSPORA (and PARABAENA) species (Menispermaceae) has been studied. The main components were generally the protoberberine bases berberine and palmatine, with jatrorrhizine an occasional minor constituent, and the aporphine base magnoflorine. Choline was also often present. Only magnoflorine was detected in the PARABAENA material examined. PMID:17404996

  16. 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.

  17. Influence of Some Heavy Metals on Growth, Alkaloid Content and Composition in Catharanthus roseus L.

    OpenAIRE

    Srivastava, N. K.; A.K. Srivastava

    2010-01-01

    Shoot biomass production, alkaloid content and composition as influence by cadmium, manganese, nickel and lead at uniform dose of 5 mM were investigated in Catharanthus roseus plants grown in sand culture. Treatment with Mn, Ni, and Pb significantly enhanced total root alkaloid accumulation. Cd and Ni treatment resulted in two-fold where as Pb treatment resulted in three fold increase in serpentine content of roots. The non-significant affect on biomass suggests that plants can withstand meta...

  18. Relationship between alkaloid contents and growth environment of Yimu Cao (Herba Leonuri)

    Institute of Scientific and Technical Information of China (English)

    CHAO Zhi; YAN Gang

    2001-01-01

    To study the relationship between alkaloids contents in Chinese traditional drug Yimu Cao (the dried aerial parts ofLeonurus artemisia) and its growing environment. Methods: Samples of the drug and the soil at the growing site collected from 5 selected regions. Reference materials were checked and on-the-spot observations were carried out to investigate the growth environment. RP-HPLC was performed to determine the alkaloid contents in the drug. Results: Different regions had different environmental conditions, including climate, soil, vegetation, and so on.No matter barren or fertile the soil at the growing site was, the herb ofL. Artemisia could grow well, but the contents of alkaloid in the drug varied greatly. The drugs produced in 2 northern regions, where the soil is alkaline, had higher content of alkaloid (about 0.4%) than that produced in southern regions (0.1%-0.2%), where the soil is acid. Conclusion:The contents of organic matters, effective phosphorus, quick-acting potassium, and the pH value of the growing site soil were the factors correlating with alkaloid contents in the drug, among which the pH value of soil was an important positively correlating factor. The alkaline soils in North benefit the accumulation of alkaloids more than the acid soils in South. The other probable elements affecting the alkaloid contents in Yimu Cao were climate and genetic factors.

  19. Bacterial Alkaloids Prevent Amoebal Predation.

    Science.gov (United States)

    Klapper, Martin; Götze, Sebastian; Barnett, Robert; Willing, Karsten; Stallforth, Pierre

    2016-07-25

    Bacterial defense mechanisms have evolved to protect bacteria against predation by nematodes, predatory bacteria, or amoebae. We identified novel bacterial alkaloids (pyreudiones A-D) that protect the producer, Pseudomonas fluorescens HKI0770, against amoebal predation. Isolation, structure elucidation, total synthesis, and a proposed biosynthetic pathway for these structures are presented. The generation of P. fluorescens gene-deletion mutants unable to produce pyreudiones rendered the bacterium edible to a variety of soil-dwelling amoebae. PMID:27294402

  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....... The indole alkaloids were primarily of the iboga-type and constituted ca 3% of the dried bark and 20% of the total extracts. The major alkaloids were coronaridine, (19S)-heyneanine, voacangine and ibogamine. Among the minor components, four new alkaloids were identified: 5,6-dehydro-coronaridine, 3R...

  1. An analysis of Sorghum halepense’s behavior in presence of tropane alkaloids from Datura stramonium extracts

    Directory of Open Access Journals (Sweden)

    Butnariu Monica

    2012-07-01

    Full Text Available Abstract Background This study aimed to quantify the allelopathic potential of Datura stramonium (Jimson weed. Sorghum halepense (Johnsongrass tolerance was assessed by germinating, seed and growing seedlings, dosing of photo-synthesis pigments, followed by treatment with D. stramonium extract tropane alkaloids. Results Preliminary chemical analysis of the extracts showed the presence of alkaloids. The presence of alkaloids was confirmed through HPLC–UV system analysis. Various concentrations of analytic purity alkaloids had similar effects on germination and development of S. halepense’s root systems with those of extracts from of D. stramonium. Germination was not affected by any of the tested extracts, but growth was inhibited by the presence of tropane alkaloids. Extracts had effects at higher alkaloid concentrations. Seedlings of S. halepense developed toxicity symptoms in the presence of alkaloid extracts, but the occurrence of several chlorotic and necrotic areas was noticed in the flower extract biotest. Conclusions Results show that the tested species is sensitive to alkaloids in their growth environment. This research justifies the fact that aqueous extracts from D. stramonium are adequate to the situations in which S. halepense becomes damaging.

  2. An analysis of Sorghum halepense’s behavior in presence of tropane alkaloids from Datura stramonium extracts

    Science.gov (United States)

    2012-01-01

    Background This study aimed to quantify the allelopathic potential of Datura stramonium (Jimson weed). Sorghum halepense (Johnsongrass) tolerance was assessed by germinating, seed and growing seedlings, dosing of photo-synthesis pigments, followed by treatment with D. stramonium extract tropane alkaloids. Results Preliminary chemical analysis of the extracts showed the presence of alkaloids. The presence of alkaloids was confirmed through HPLC–UV system analysis. Various concentrations of analytic purity alkaloids had similar effects on germination and development of S. halepense’s root systems with those of extracts from of D. stramonium. Germination was not affected by any of the tested extracts, but growth was inhibited by the presence of tropane alkaloids. Extracts had effects at higher alkaloid concentrations. Seedlings of S. halepense developed toxicity symptoms in the presence of alkaloid extracts, but the occurrence of several chlorotic and necrotic areas was noticed in the flower extract biotest. Conclusions Results show that the tested species is sensitive to alkaloids in their growth environment. This research justifies the fact that aqueous extracts from D. stramonium are adequate to the situations in which S. halepense becomes damaging. PMID:22839364

  3. Intraspecific variability in the alkaloid metabolism of Galanthus elwesii.

    Science.gov (United States)

    Berkov, Strahil; Sidjimova, Borjana; Evstatieva, Luba; Popov, Simeon

    2004-03-01

    Alkaloid pattern of individuals from 16 Bulgarian Galanthus elwesii populations was investigated by GC/MS and TLC. Twenty-one Amaryllidaceae alkaloids were detected and 14 of them were identified. Crinane type alkaloids, haemanthamine or crinine, dominated alkaloid metabolism in most of the populations. With exception of one population, where the separate individuals showed variable alkaloid profiles (dominated by crinine or haemanthamine) the individuals of the rest of populations have identical and characteristic alkaloid profiles. Some populations showed remarkable differences in respect to their alkaloid pattern-type of biosynthesis, main alkaloids and number of alkaloids. Populations dominated by galanthamine type alkaloids were found as well. These data demonstrate that like the morphological features, the alkaloid metabolism of G. elwesii is also variable.

  4. METABOLISM OF TOXIC PYRROLIZIDINE ALKALOIDS FROM TANSY RAGWORT, SENECIO JACOBAEA, IN BOVINE RUMINAL FLUID UNDER ANAEROBIC CONDITIONS. (R825689C006)

    Science.gov (United States)

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  5. 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 inge

  6. Alkaloids from the Roots of Saccopetalum prolificum

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    A new alkaloid, named prolifine (1), was isolated along with four known alkaloids, liriodenine (2), 6-hydroxyonychine (3), isooncodine (4) and discretamine (5) from the roots of Saccopetalum prolificum. The structure of 1 was elucidated on the basis of spectroscopic and chemical methods.

  7. Alkaloids of some Asian Sedum species

    NARCIS (Netherlands)

    Kim, JH; THart, H; Stevens, JF

    1996-01-01

    The leafy parts of 16 Asian species belonging to the three sections of Sedum were investigated for the presence of alkaloids. Only in seven species of Sedum sect. Sedum were alkaloids found. Sedum bulbiferum, S. japonicum, S. lepidopodium, S. morrisomensis, S. oryzifolium, S. polytrichoides and S. s

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

    Science.gov (United States)

    Zheng, Shaojun; Zhou, Xinping; Xu, Shixun; Zhu, Rui; Bai, Hongjin; Zhang, Jiwen

    2016-01-01

    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. PMID:27618003

  9. Rapid Screening of Ergot Alkaloids in Sclerotia by MALDI-TOF Mass Spectrometry.

    Science.gov (United States)

    Sivagnanam, Kumaran; Komatsu, Emy; Patrick, Susan; Rampitsch, Christoph; Perreault, Hélène; Gräfenhan, Tom

    2016-07-01

    Ergot is a common disease of wheat and other cereal grains that is predominantly caused by Claviceps purpurea in the field, often affecting crop yield in addition to the environment. Infected grain can be contaminated with dark sclerotia, which contain fungal metabolites such as ergot alkaloids. The occurrence of ergot alkaloids in cereal grain is a major health concern for humans and livestock. Effective and rapid screening of these mycotoxins is crucial for producers, processors, and consumers of cereal-based food and feed grain. Established methods of ergot alkaloid screening based on LC-MS or GC-MS require laborious processes. A novel method using matrix-assisted laser desorption ionization (MALDI)-time-of-flight (TOF) MS was developed to identify four ergot alkaloids. Using dihydroxybenzoic acid as the matrix, ergosine, ergocornine, ergocryptine, and ergocristine were readily detected in individual sclerotia of C. purpurea. The accuracy of the identified ergot alkaloids was further confirmed by tandem MS analysis. MALDI-TOF MS is suitable for high-throughput screening of ergot alkaloids because it permits rapid and accurate identification, simple sample preparation, and no derivatization or chromatographic separation. PMID:27455930

  10. Binary stress induces an increase in indole alkaloid biosynthesis in Catharanthus roseus.

    Science.gov (United States)

    Zhu, Wei; Yang, Bingxian; Komatsu, Setsuko; Lu, Xiaoping; Li, Ximin; Tian, Jingkui

    2015-01-01

    Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abundance of proteins related to tricarboxylic acid cycle and cell wall was largely increased; while, that of proteins related to tetrapyrrole synthesis and photosynthesis was decreased. Of note, 10-hydroxygeraniol oxidoreductase, which is involved in the biosynthesis of indole alkaloid was two-fold more abundant in treated group compared to the control. In addition, mRNA expression levels of genes involved in the indole alkaloid biosynthetic pathway indicated an up-regulation in their transcription in C. roseus under UV-B irradiation. These results suggest that binary stress might negatively affect the process of photosynthesis in C. roseus. In addition, the induction of alkaloid biosynthesis appears to be responsive to binary stress. PMID:26284098

  11. Binary Stress Induces an Increase in Indole Alkaloid Biosynthesis in Catharanthus roseus

    Directory of Open Access Journals (Sweden)

    Wei eZhu

    2015-07-01

    Full Text Available Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abundance of proteins related to tricarboxylic acid cycle and cell wall was largely increased; while, that of proteins related to tetrapyrrole synthesis and photosynthesis was decreased. Of note, 10-hydroxygeraniol oxidoreductase, which is involved in the biosynthesis of indole alkaloid was two-fold more abundant in treated group compared to that in control. In addition, mRNA expression levels of genes involved in the indole alkaloid biosynthetic pathway indicated an up-regulation in their transcription in C. roseus under UV-B irradiation. These results suggest that binary stress might negatively affect the process of photosynthesis in C. roseus. In addition, the induction of alkaloid biosynthesis appears to be responsive to binary stress.

  12. 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

  13. Genetic variation in alkaloid accumulation in leaves of Nicotiana

    Institute of Scientific and Technical Information of China (English)

    Bo SUN; Fen ZHANG; Guo-jun ZHOU; Guo-hai CHU; Fang-fang HUANG; Qiao-mei WANG; Li-feng JIN; Fu-cheng LIN; Jun YANG

    2013-01-01

    Alkaloids are plant secondary metabolites that are widely distributed in Nicotiana species and contribute greatly to the quality of tobacco leaves. Some alkaloids, such as nornicotine and myosmine, have adverse effects on human health. To reduce the content of harmful alkaloids in tobacco leaves through conventional breeding, a genetic study of the alkaloid variation among different genotypes is required. In this study, alkaloid profiles in leaves of five Nicotiana tabacum cultivars and Nicotiana tomentosiformis were investigated. Six alkaloids were identified from al six genotypes via gas chromatograph-mass spectrometry (GC-MS). Significant differences in alkaloid content were ob-served both among different leaf positions and among cultivars. The contents of nornicotine and myosmine were positively and significantly correlated (R2=0.881), and were also separated from those of other alkaloids by clustering. Thus, the genotype plays a major role in alkaloid accumulation, indicating a high potential for manipulation of alkaloid content through traditional breeding.

  14. Bioactive acridone alkaloids from Swinglea glutinosa.

    Science.gov (United States)

    Weniger, B; Um, B H; Valentin, A; Estrada, A; Lobstein, A; Anton, R; Maillé, M; Sauvain, M

    2001-09-01

    A new prenylated acridone alkaloid, 1,3,5-trihydroxy-2,8-bis(3-methylbut-2-enyl)-10-methyl-9-acridone (1), was isolated from the stembark of Swinglea glutinosa, along with three known acridone alkaloids, 5-hydroxynoracronycine (2), 1,3,5-trihydroxy-4-methoxy-2-(3-methylbut-2-enyl)-10-methyl-9-acridone (3), and 1,3,5-trihydroxy-4-methoxy-10-methylacridone (4). The isolated alkaloids were assessed in vitro against chloroquine-sensitive and -resistant Plasmodium falciparum strains and for cytotoxicity using HeLa cells. PMID:11575960

  15. Norditerpenoid Alkaloids from Aconitum spicatum Stapf

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    To search for pharmacologically and structurally interesting substances from traditional Chinese medicines,we investigated the chemical compounds of Aconitum spicatum Stapf. Two new norditerpenoid alkaloids,namely spicatine A (compound 1) and spicatine B (compound 2), as well as 11 known norditerpenoid alkaloids were isolated from the CHCl3 portion of the 90% ethanol extract of the roots of A. spicatum. The structures of the alkaloids were characterized on the basis of their spectral data, One of the isolated compounds showed significant cytotoxic activities (IC50 values < 200 μmol/L) against the HL-60 cell line.

  16. The inhibition activity of selected beta-carboline alkaloids on enzymes of acetylcholinesterase and butyrylcholinesterase.

    Science.gov (United States)

    Krsková, Zuzana; Martin, Jan; Dusek, Jaroslav

    2011-06-01

    This thesis deals with testing of inhibition activity beta-carboline alkaloids on activity of enzymes acetylcholinesterase (ACHE) and butyrylcholinesterase (BUCHE) using test "Fast Blue B salt" at TLC desk and Ellman's test using spectrophotometer. It was also investigated how dimethylsulfoxide used as a solvent in combination with water affects activity of enzymes and alkaloids. Results show harmine in form of base and salt in water and in mixture of DMSO and water has the hightest inhibition activity on ACHE using eserine as reference substance. Harmalol in form of salt in water and harmine in form of base and salt in mixture of DMSO and water has the hightest activity on BUCHE. It was find out that DMSO considerably affects activity of enzymes and alkaloids. PMID:21838142

  17. Synthesis of the isoquinoline alkaloid, crispine C

    OpenAIRE

    Blair, A.; Stevenson, L; Sutherland, A

    2012-01-01

    The first total synthesis of the isoquinoline alkaloid, crispine C is described in seven steps using a Henry reaction and the Pictet–Gams variant of the Bischler–Napieralski reaction to effect the key transformations.

  18. Anxiolytic Activity of Diterpene Alkaloid Songorine.

    Science.gov (United States)

    Nesterova, Yu V; Povet'eva, T N; Suslov, N I; Shults, E E; Ziuz'kov, G N; Aksinenko, S G; Afanas'eva, O G; Krapivin, A V; Kharina, T G

    2015-09-01

    Antianxiety action of diterpene alkaloid songorine was studied using Vogel conflict test. Songorine in a dose of 0.25 mg/kg demonstrated high anxiolytic activity comparable to that of phenazepam and produced no sedative effect.

  19. Enrichment and purification of six Aconitum alkaloids from Aconiti kusnezoffii radix by macroporous resins and quantification by HPLC-MS.

    Science.gov (United States)

    Liu, Jingjing; Li, Qing; Liu, Ran; Yin, Yidi; Chen, Xiaohui; Bi, Kaishun

    2014-06-01

    Aconitine, mesaconitine, hypaconitine, benzoylaconine, benzoylmesaconine and benzoylhypaconine are six main Aconitum alkaloids from traditional Chinese medicine, Aconiti kusnezoffii radix, which possess highly bioactive as well as highly toxic character for medicinal use. In the present study, for the purpose of better utilizing the toxic herbal material, the performance characteristics of NKA-II, D101, X-5, AB-8, S-8, HPD722 and HPD750 macroporous resins for the enrichment and purification of these six Aconitum alkaloids were critically evaluated. Results showed that NKA-II offered the best adsorption and desorption capacities for six Aconitum alkaloids among the seven macroporous resins tested, which were affected significantly by the pH value. Subsequently, dynamic adsorption and desorption experiments had been carried out with the column packed by NKA-II resin to optimize the separation process of six Aconitum alkaloids. After one run treatment with NKA-II resin, the content of total six Aconitum alkaloids were increased from 5.87% to 60.3%, the recovery was 75.8%. Meanwhile, a validated HPLC-MS method had been developed to qualitative and quantitative these six Aconitum alkaloids. This method would provide scientific references to the large-scale production of six Aconitum alkaloids from Aconiti kusnezoffii radix or other plants and might also expand the secure application of these highly toxic components for pharmacy. PMID:24814003

  20. Polycyclic alkaloids via transannular Mannich reactions

    DEFF Research Database (Denmark)

    Vital, Paulo; Hosseini, Masood; Shanmugham, M. S.;

    2009-01-01

    The tricyclic compound 13, representing the framework of the cylindricine 4 and lepadiformine 5 alkaloids, was prepared in a single operation via the first example of a transannular Mannich reaction involving a macrocyclic diketoamine 12.......The tricyclic compound 13, representing the framework of the cylindricine 4 and lepadiformine 5 alkaloids, was prepared in a single operation via the first example of a transannular Mannich reaction involving a macrocyclic diketoamine 12....

  1. Alkaloids from Fissistigma latifolium (Dunal) Merr.

    OpenAIRE

    Asmah Alias; Hazrina Hazni; Faridahanim Mohd Jaafar; Khalijah Awang; Nor Hadiani Ismail

    2010-01-01

    A phytochemical study of the bark of Fissistigma latifolium (Annonaceae) yielded a new aporphine alkaloid, (-)-N-methylguattescidine (1), and eight known alkaloids: liriodenine (2), oxoxylopine (3), (-)-asimilobine (4), dimethyltryptamine (5), (-)-remerine (6), (-)-anonaine (7), columbamine (8) and lysicamine (9). The compounds were isolated using various chromatographic methods and structural elucidation was accomplished by means of spectroscopic methods, notably 1D-NMR (1H, 13C, DEPT), 2D-N...

  2. Alkaloids from Fissistigma latifolium (Dunal Merr.

    Directory of Open Access Journals (Sweden)

    Asmah Alias

    2010-06-01

    Full Text Available A phytochemical study of the bark of Fissistigma latifolium (Annonaceae yielded a new aporphine alkaloid, (--N-methylguattescidine (1, and eight known alkaloids: liriodenine (2, oxoxylopine (3, (--asimilobine (4, dimethyltryptamine (5, (--remerine (6, (--anonaine (7, columbamine (8 and lysicamine (9. The compounds were isolated using various chromatographic methods and structural elucidation was accomplished by means of spectroscopic methods, notably 1D-NMR (1H, 13C, DEPT, 2D-NMR (COSY, HMQC, HMBC, UV, IR and MS.

  3. Two new diterpene alkaloids from Delphinium chrysotrichum

    Institute of Scientific and Technical Information of China (English)

    Yang Qing He; Xiao Mei Wei; Yi Li Han; Li Ming Gao

    2007-01-01

    Chemical investigation on the ethanol extract from the whole plants of Delphinium chrysotrichum resulted in the isolation of two new diterpene alkaloids named delphatisine A (1) and delphatisine B (2), respectively. The structures of the new compounds were deduced on the basis of their spectral data (IR, HREIMS, EIMS, 1D, 2D-NMR). This is the first report on the isolation of diterpenoid alkaloids from the D. Chrysotrichum.

  4. Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.

    Science.gov (United States)

    Slaninová, I; Táborská, E; Bochoráková, H; Slanina, J

    2001-01-01

    We compared the effects of four quaternary benzo[c]phenanthridine alkaloids--chelerythrine, chelilutine, sanguinarine, and sanguilutine--and two quaternary protoberberine alkaloids-berberine and coptisine--on the human cell line HeLa (cervix carcinoma cells) and the yeasts Saccharomyces cerevisiae and Schizosaccharomyces japonicus var. versatilis. The ability of alkaloids to display primary fluorescence, allowed us to record their dynamics and localization in cells. Cytotoxic, anti-microtubular, and anti-actin effects in living cells were studied. In the yeasts, neither microtubules nor cell growth was seriously affected even at the alkaloid concentration of 100 microg/ml. The HeLa cells, however, responded to the toxic effect of alkaloids at concentrations ranging from 1 to 50 microg/ml. IC50 values for individual alkaloids were: sanguinarine IC50 = 0.8 microg/ml, sanguilutine IC50 = 8.3 microg/ml, chelerythrine IC50 = 6.2 microg/ml, chelilutine IC50 = 5.2 microg/ml, coptisine IC50 = 2.6 microg/ml and berberine IC50 > 10.0 microg/ml. In living cells, sanguinarine produced a decrease in microtubule numbers, particularly at the cell periphery, at a concentration of 0.1 microg/ml. The other alkaloids showed a similar effect but at higher concentrations (5-50 microg/ml). The strongest effects of sanguinarine were explained as a consequence of its easy penetration through the cell membrane owing to nonpolar pseudobase formation and to a high degree of molecular planarity.

  5. Relationships among Ergot Alkaloids, Cytochrome P450 Activity, and Beef Steer Growth

    Science.gov (United States)

    Rosenkrans, Charles; Ezell, Nicholas

    2015-03-01

    Determining a grazing animal’s susceptibility to ergot alkaloids has been a research topic for decades. Our objective was to determine if the Promega™ P450-Glo assay could be used to indirectly detect ergot alkaloids or their metabolites in urine of steers. The first experiment validated the effects of ergot alkaloids [0, 20, and 40 μM of ergotamine (ET), dihydroergotamine (DHET), and ergonovine (EN)] on human CYP3A4 using the P450-Glo assay (Promega™ V9800). With this assay, luminescence is directly proportional to CYP450 activity. Relative inhibition of in vitro cytochrome P450 activity was affected (P experiment 2, urine was collected from Angus-sired crossbred steers (n = 39; 216 ± 2.6 d of age; 203 ± 1.7 kg) after grazing tall fescue pastures for 105 d. Non-diluted urine was added to the Promega™ P450-Glo assay, and observed inhibition (3.7 % ± 2.7 of control). Urine content of total ergot alkaloids (331.1 ng/mg of creatinine ± 325.7) was determined using enzyme linked immunosorbent assay. Urine inhibition of CYP450 activity and total alkaloids were correlated (r = -0.31; P animals that are susceptible to ergot alkaloids. Although, additional research is needed, we demonstrate that the Promega™ P450-Glo assay is sensitive to ergot alkaloids and urine from steers grazing tall fescue. With some refinement the P450-Glo assay has potential as a tool for screening cattle for their exposure to fescue toxins.

  6. 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

  7. Activities and Effects of Ergot Alkaloids on Livestock Physiology and Production

    Directory of Open Access Journals (Sweden)

    James L. Klotz

    2015-07-01

    Full Text Available Consumption of feedstuffs contaminated with ergot alkaloids has a broad impact on many different physiological mechanisms that alters the homeostasis of livestock. This change in homeostasis causes an increased sensitivity in livestock to perturbations in the ambient environment, resulting in an increased sensitivity to such stressors. This ultimately results in large financial losses in the form of production losses to livestock producers around the world. This review will focus on the underlying physiological mechanisms that are affected by ergot alkaloids that lead to decreases in livestock production.

  8. Activities and Effects of Ergot Alkaloids on Livestock Physiology and Production.

    Science.gov (United States)

    Klotz, James L

    2015-08-01

    Consumption of feedstuffs contaminated with ergot alkaloids has a broad impact on many different physiological mechanisms that alters the homeostasis of livestock. This change in homeostasis causes an increased sensitivity in livestock to perturbations in the ambient environment, resulting in an increased sensitivity to such stressors. This ultimately results in large financial losses in the form of production losses to livestock producers around the world. This review will focus on the underlying physiological mechanisms that are affected by ergot alkaloids that lead to decreases in livestock production. PMID:26226000

  9. 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. PMID:24671624

  10. 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.

  11. Two New C19-Diterpenoid Alkaloids from Delphinium davidii Franch.

    Institute of Scientific and Technical Information of China (English)

    Xiao Xia LIANG; Dong Lin CHEN; Feng Peng WANG

    2006-01-01

    Two new C19-diterpenoid alkaloids, davidisines A (1) and B (2) along with thirteen known alkaloids were isolated from the whole herb of Delphinium davidii Franch. Their structures were established by spectral methods, especially 2D NMR techniques.

  12. Biosynthesis of Monoterpenoid Indole Alkaloid Ajmaline Catalyzed by Novel Reductases

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    @@ Introduction One of the major root alkaloids of the Indian medicinal plant Rauvolfia serpenlina Benth. Ex Kurz is named ajmaline. The enzymatic biosynthesisof this alkaloid has been studied for a long time by our group[1].

  13. Biological activity of alkaloids from Solanum dulcamara L.

    Science.gov (United States)

    Kumar, Padma; Sharma, Bindu; Bakshi, Nidhi

    2009-01-01

    Alkaloids are well known for their antimicrobial activity. Though all natural alkaloids come from plants, not all plants produce alkaloids. Plants of the Solanaceae family are known for their high alkaloid content. Alkaloids are found in all plant parts like roots, stems, leaves, flowers, fruits and seeds. In the present study, those plant parts of Solanum dulcamara were selected which have been reported to produce a high content of a specific alkaloid: solanine (from unripe fruits), solasodine (from flowers) and beta-solamarine (from roots). These alkaloids were extracted from various parts of S. dulcamara by well-established methods and were screened for their antibacterial activity. Human pathogenic bacteria, viz., Enterobacter aerogenes, Escherichia coli, Staphylococcus aureus, were selected for the study. All three alkaloids inhibited the growth of E. coli and S. aureus. However, no significant activity was observed against E. aerogenes. Minimum inhibitory concentration and minimum bactericidal concentration were also evaluated.

  14. Monoterpenoid Indole Alkaloids from Catharanthus roseus Cultivated in Yunnan.

    Science.gov (United States)

    Wang, Bei; Liu, Lu; Chen, Ying-ying; Li, Qiong; Li, Dan; Liu, Va-ping; Luo, Xiao-dong

    2015-12-01

    A new monoterpenoid indole alkaloid, 15,20-dehydro-3α-(2-oxopropyl) coronaridine (1), along with sixteen analogues (2-17) were isolated from the leaves of Catharanthus roseus cultivated in Yunnan. The new alkaloid was elucidated on the basis of extensive spectroscopic analysis, and the known alkaloids were identified by comparison with the reported spectroscopic data. Among them, alkaloid 16 was isolated from Catharanthus for the first time. PMID:26882670

  15. An efficient synthesis of loline alkaloids

    Science.gov (United States)

    Cakmak, Mesut; Mayer, Peter; Trauner, Dirk

    2011-07-01

    Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. It has been known for more than a century and has been the subject of extensive biological investigations, but only two total syntheses have been achieved to date. Here, we report an asymmetric total synthesis of loline that, with less then ten steps, is remarkably short. Our synthesis incorporates a Sharpless epoxidation, a Grubbs olefin metathesis and an unprecedented transannular aminobromination, which converts an eight-membered cyclic carbamate into a bromopyrrolizidine. The synthesis is marked by a high degree of chemo- and stereoselectivity and gives access to several members of the loline alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex interactions between plants, fungi, insects and bacteria brokered by loline alkaloids.

  16. 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.

  17. Aporphine alkaloids from Ocotea macrophylla (Lauraceae)

    Energy Technology Data Exchange (ETDEWEB)

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

    2010-07-01

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

  18. Aporphine alkaloids from Ocotea macrophylla (Lauraceae

    Directory of Open Access Journals (Sweden)

    Ludy Cristina Pabon

    2010-01-01

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

  19. Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids.

    Science.gov (United States)

    Hufford, C D; Sharma, A S; Oguntimein, B O

    1980-10-01

    Liriodenine was evaluated for its antibacterial and antifungal activity against several microorganisms. Other related oxoaporphine alkaloids also were evaluated. Attempts to prepare oxoaporphine alkaloids from N-acetylnoraporphines were unsuccessful, but an unexpected phenanthrene alkaloid was obtained. A novel N-demethylation reaction was noted when oxogaucine methiodide and liriodenine methiodide were treated with alumina. PMID:7420287

  20. Determining important parameters related to cyanobacterial alkaloid toxin exposure

    Energy Technology Data Exchange (ETDEWEB)

    Love, A H

    2005-09-16

    Science-based decision making required robust and high-fidelity mechanistic data about the system dynamics and impacts of system changes. Alkaloid cyanotoxins have the characteristics to warrant consideration for their potential threat. Since insufficient information is available to construct a systems model for the alkaloid cyanotoxins, saxitoxins, anatoxins, and anatoxin-a(S), an accurate assessments of these toxins as a potential threat for use for intentional contamination is not possible. Alkaloid cyanotoxin research that contributed to such a model has numerous areas of overlap for natural and intentional health effects issues that generates dual improvements to the state of the science. The use of sensitivity analyses of systems models can identify parameters that, when determined, result in the greatest impact to the overall system and may help to direct the most efficient use of research funding. This type of modeling-assisted experimentation may allow rapid progress for overall system understanding compared to observational or disciplinary research agendas. Assessment and management of risk from intentional contamination can be performed with greater confidence when mechanisms are known and the relationships between different components are validated. This level of understanding allows high-fidelity assessments that do not hamper legitimate possession of these toxins for research purposes, while preventing intentional contamination that would affect public health. It also allows for appropriate response to an intentional contamination event, even if the specific contamination had not been previous considered. Development of science-based decision making tools will only improve our ability to address the new requirements addressing potential threats to our nation.

  1. Relationships among Ergot Alkaloids, Cytochrome P450 Activity, and Beef Steer Growth

    Directory of Open Access Journals (Sweden)

    Charles F. Rosenkrans

    2015-03-01

    Full Text Available Determining a grazing animal’s susceptibility to ergot alkaloids has been a research topic for decades. Our objective was to determine if the Promega™ P450-Glo assay could be used to indirectly detect ergot alkaloids or their metabolites in urine of steers. The first experiment validated the effects of ergot alkaloids [0, 20, and 40 μM of ergotamine (ET, dihydroergotamine (DHET, and ergonovine (EN] on human CYP3A4 using the P450-Glo assay (Promega™ V9800. With this assay, luminescence is directly proportional to CYP450 activity. Relative inhibition of in vitro cytochrome P450 activity was affected (P < 0.001 by an interaction between alkaloids and concentration. That interaction resulted in no concentration effect of EN, but within ET and DHET 20 and 40 µM concentrations inhibited CYP450 activity when compared with controls. In experiment 2, urine was collected from Angus-sired crossbred steers (n = 39; 216 ± 2.6 d of age; 203 ± 1.7 kg after grazing tall fescue pastures for 105 d. Non-diluted urine was added to the Promega™ P450-Glo assay, and observed inhibition (3.7 % ± 2.7 of control. Urine content of total ergot alkaloids (331.1 ng/mg of creatinine ± 325.7 was determined using enzyme linked immunosorbent assay. Urine inhibition of CYP450 activity and total alkaloids were correlated (r = -0.31; P < 0.05. Steers were genotyped at CYP450 single nucleotide polymorphism, C994G. Steer genotype affected (P < 0.03 inhibition of CYP450 activity by urine; heterozygous steers had the least amount of CYP450 inhibition suggesting that genotyping cattle may be a method of identifying animals that are susceptible to ergot alkaloids. Although, additional research is needed, we demonstrate that the Promega™ P450-Glo assay is sensitive to ergot alkaloids and urine from steers grazing tall fescue. With some refinement the P450-Glo assay has potential as a tool for screening cattle for their exposure to fescue toxins.

  2. Antimicrobial hasubanalactam alkaloid from Stephania glabra.

    Science.gov (United States)

    Semwal, Deepak Kumar; Rawat, Usha

    2009-03-01

    A novel hasubanalactam alkaloid, named glabradine, has been isolated from the tubers of Stephania glabra, together with three known quaternary protoberberine alkaloids, palmatine, dehydrocorydalmine and stepharanine. The structure of glabradine was assigned as 7-O-demethyl-N,O-dimethyloxostephinine, by means of rigorous spectroscopic analysis including 2 D NMR measurements. It was evaluated for antimicrobial activity against Staphylococcus aureus, S. mutans, Microsporum gypseum, M. canis and Trichophyton rubrum and displayed potent antimicrobial activity superior to those of novobiocin and erythromycin used as positive controls. PMID:19148860

  3. Antiprotozoal alkaloids from Psychotria prunifolia (Kunth) Steyerm

    Energy Technology Data Exchange (ETDEWEB)

    Kato, Lucilia; Oliveira, Cecilia M.A. de; Faria, Emiret O.; Ribeiro, Laryssa C.; Carvalho, Brenda G., E-mail: lucilia@quimica.ufg.br [Instituto de Quimica, Universidade Federal de Goias, Campus II, Samambaia, Goiania, GO (Brazil); Silva, Cleuza C. da; Santin, Silvana M.O. [Departamento de Quimica, Universidade Estadual de Maringa, Maringa, PR (Brazil); Schuque, Ivania T.A.; Nakamura, Celso V.; Britta, Elisandra A.; Miranda, Nathielle [Departamento de Farmacia e Farmacologia, Universidade Estadual de Maringa, PR (Brazil); Iglesias, Amadeu H. [Waters Technologies do Brasil LTDA, Barueri, SP (Brazil); Delprete, Piero G. [VHerbier de Guyane, Institut de Recherche pour le Developpement (IRD), UMR AMAP, French Guiana (France)

    2012-07-01

    The continuity of the phyto chemical study of crude extracts of P. prunifolia's roots and branches led to the isolation of five indole-{beta}-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{sub 50} values of 16.0 and 40.7 {mu}g per mL, respectively. (author)

  4. Total Synthesis of the Zoanthamine Alkaloid

    Institute of Scientific and Technical Information of China (English)

    M. Miyashita

    2005-01-01

    @@ 1Introduction The zoanthamine alkaloids, a type of heptacyclic marine alkaloid isolated from colonial zoanthids of the genus Zoanthus sp., have attracted much attention from a wide area of science, because of their distinctive biological and pharmacological properties as well as their chemical structures with stereochemical complexity.Namely, norzoanthamine (1)[1] can suppress the loss of bone weight and strength in ovariectomized mice and has been considered a promising candidate for an antiosteoporotic drug[1], whereas zoanthamine (2)[2] has exhibited potent inhibitory activity toward phorbol myristate-induced inflammation in addition to powerful analgesic effects[2]. See Fig. 1.

  5. Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test.

    Science.gov (United States)

    Mohamed, A F; Matsumoto, K; Tabata, K; Takayama, H; Kitajima, M; Watanabe, H

    2000-12-01

    The effects of Uncaria tomentosa total alkaloid and its oxindole alkaloid components, uncarine E, uncarine C, mitraphylline, rhynchophylline and isorhynchophylline, on the impairment of retention performance caused by amnesic drugs were investigated using a step-down-type passive avoidance test in mice. In this test, the retention performance of animals treated with the amnesic and test drugs before training was assessed 24 h after training. Uncaria tomentosa total alkaloid (10-20 mg kg(-1), i.p.) and the alkaloid components (10-40 mg kg(-1), i.p.), as well as the muscarinic receptor agonist oxotremorine (0.01 mg kg(-1), i.p.), significantly attenuated the deficit in retention performance induced by the muscarinic receptor antagonist scopolamine (3 mg kg(-1), i.p.). The effective doses of uncarine C and mitraphylline were larger than those of other alkaloid components. Uncarine E (20 mg kg(-1), i.p.) also blocked the impairment of passive avoidance performance caused by the nicotinic receptor antagonist mecamylamine (15 mg kg(-1), i.p.) and the N-methyl-D-aspartate (NMDA) receptor antagonist (+/-)-3-(2-carboxypiperazin-4-yl)-propyl-1-phosphonic acid (CPP; 7.5 mg kg(-1), i.p.), but it failed to affect the deficit caused by the benzodiazepine receptor agonist diazepam (2 mg kg(-1), i.p.). Rhynchophylline significantly reduced the mecamylamine-induced deficit in passive avoidance behaviour, but it failed to attenuate the effects of CPP and diazepam. These results suggest that Uncaria tomentosa total alkaloids exert a beneficial effect on memory impairment induced by the dysfunction of cholinergic systems in the brain and that the effect of the total alkaloids is partly attributed to the oxindole alkaloids tested. Moreover, these findings raised the possibility that the glutamatergic systems are implicated in the anti-amnesic effect of uncarine E.

  6. Hydrofocusing Bioreactor Produces Anti-Cancer Alkaloids

    Science.gov (United States)

    Gonda, Steve R.; Valluri, Jagan V.

    2011-01-01

    A methodology for growing three-dimensional plant tissue models in a hydrodynamic focusing bioreactor (HFB) has been developed. The methodology is expected to be widely applicable, both on Earth and in outer space, as a means of growing plant cells and aggregates thereof under controlled conditions for diverse purposes, including research on effects of gravitation and other environmental factors upon plant growth and utilization of plant tissue cultures to produce drugs in quantities greater and at costs lower than those of conventional methodologies. The HFB was described in Hydro focus - ing Bioreactor for Three-Dimensional Cell Culture (MSC-22358), NASA Tech Briefs, Vol. 27, No. 3 (March 2003), page 66. To recapitulate: The HFB offers a unique hydrofocusing capability that enables the creation of a low-shear liquid culture environment simultaneously with the herding of suspended cells and tissue assemblies and removal of unwanted air bubbles. The HFB includes a rotating cell-culture vessel with a centrally located sampling port and an internal rotating viscous spinner attached to a rotating base. The vessel and viscous spinner can be made to rotate at the same speed and direction or different speeds and directions to tailor the flow field and the associated hydrodynamic forces in the vessel in order to obtain low-shear suspension of cells and control of the locations of cells and air bubbles. For research and pharmaceutical-production applications, the HFB offers two major benefits: low shear stress, which promotes the assembly of cells into tissue-like three-dimensional constructs; and randomization of gravitational vectors relative to cells, which affects production of medicinal compounds. Presumably, apposition of plant cells in the absence of shear forces promotes cell-cell contacts, cell aggregation, and cell differentiation. Only gentle mixing is necessary for distributing nutrients and oxygen. It has been postulated that inasmuch as cells in the simulated

  7. Alkaloid diversity in Galanthus elwesii and Galanthus nivalis.

    Science.gov (United States)

    Berkov, Strahil; Bastida, Jaume; Sidjimova, Borjana; Viladomat, Francesc; Codina, Carles

    2011-01-01

    Seventy alkaloids of galanthamine, lycorine, homolycorine, tazettine, haemanthamine, narciclasine, and tyramine types were detected by GC/MS in 25 Galanthus elwesii and seven Galanthus nivalis populations, collected from different locations in Bulgaria. Intraspecies diversity in the alkaloid profiles regarding the main alkaloid types (chemotypes) was observed. Tyramine-type protoalkaloids (namely, hordenine and its derivatives) were dominant in 19 populations of G. elwesii. In other populations of G. elwesii, the plants accumulated mainly homolycorine-, lycorine-, and galanthamine-type alkaloids. The alkaloid profiles of G. nivalis were dominated by narciclasine-, galanthamine-, lycorine-, haemanthamine-, or tazettine-type compounds. Geographical distribution of chemotypes indicated a relationship between populations, since adjacent populations often displayed similar alkaloid profiles. The results from year-to-year sampling and transplantation experiments imply genetic determination of alkaloid synthesis in the two studied species of Galanthus.

  8. A New Quinolizidine Alkaloid from Boehmeria siamensis

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    A new quinolizidine alkaloid, 3-(4-hydroxyphenyl)-4-(3-methoxy-4-hydroxyphenyl)-3, 4-dehydroquinolizidine (1), was isolated from the ethanol extract of the whole plants of Boehmeria siamensis Craib. Its structure was elucidated on the analysis of 1D NMR and 2D NMR spectrum.

  9. Two New Oxoaporphine Alkaloids from Thalictrum elegans

    Institute of Scientific and Technical Information of China (English)

    梁志远; 杨小生; 汪冶; 郝小江

    2005-01-01

    Two new oxoaporphine alkaloids, 1,2,3,10-tetramethoxy-9-(2-hydroxy-4,5-dimethoxybenzyloxy)oxoaporphine (1) and 1,2,3,10-tetramethoxy-9-(4,5-dimethoxy-2-formylphenoxy)oxoaporphine (2), were isolated from Thalictrum elegans. Their structures were elucidated based on spectroscopic analysis including 1D, 2D NMR, IR and MS.

  10. Saponins and alkaloids from Abuta grandifolia

    OpenAIRE

    Sayagh, C.; Long, C; Moretti, Christian; Lavaud, C.

    2012-01-01

    Five new bidesmosidic saponins (1-5), along with six known triterpenoid saponins, were isolated from the methanolic extracts of the leaves and twigs of Abuta grandifolia. The ethyl acetate extracts allowed the isolation of three tropoloisoquinolines and of one isoquinoline; all were known alkaloids. The structures of all compounds were elucidated on the basis of extensive spectroscopic data analysis.

  11. A New Alkaloid from Sinomenium acutum

    Institute of Scientific and Technical Information of China (English)

    Wei Ming CHENG; Feng QIU; Li Jun WU; Xin Sheng YAO

    2005-01-01

    Sinomenium acutum is widely used in East and South Asia for the treatment of many diseases, especially rheumatoid arthritis (RA). The chemical research on Sinomenium acutum led to the isolation of a new alkaloid compound (1). On the basis of chemical evidences and spectral analysis, 1 was identified as N-(1, 7-dimethoxylphenanthren-2-yl)acetamide.

  12. 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......, the DHQs were accompanied by six histrionicotoxins (HTXs), viz., 283A, 285A, 285B, 285C, 287A, and 287D. This co-occurrence of the HTX and DHQ alkaloids is the usual pattern seen in dendrobatid frogs. This finding contrasts with our earlier study, where workers of a Brazilian ant, Solenopsis (Diplorhoptrum......) 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...

  13. Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor

    Directory of Open Access Journals (Sweden)

    Sebastien Arseneau

    2011-11-01

    Full Text Available The bulbs and aerial parts of Zephyranthes concolor (Lindl. Benth. & Hook. f. (Amaryllidaceae, an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution 1H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution 1H- and 13C-NMR spectra were recorded. Unambiguous assignations were achieved with HMBC, and HSQC experiments, and its structure was corroborated by X-ray diffraction. Minimum energy conformation for structures of chlidanthine, and its positional isomer galanthamine, were calculated by molecular modelling. Galanthamine is a well known acetylcholinesterase inhibitor; therefore, the isolated alkaloids were tested for this activity. Chlidanthine and galanthamine N-oxide inhibited electric eel acetylcholinesterase (2.4 and 2.6 × 10−5 M, respectively, indicating they are about five times less potent than galanthamine, while galwesine was inactive at 10−3 M. Inhibitory activity of HIV-1 replication, and cytotoxicity of the isolated alkaloids were evaluated in human MT-4 cells; however, the alkaloids showed poor activity as compared with standard anti-HIV drugs, but most of them were not cytotoxic.

  14. 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.

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

    Directory of Open Access Journals (Sweden)

    Nikolić Milan

    2003-01-01

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

  16. Preparation and In vitro Evaluation of Ethosomal Total Alkaloids of Sophora alopecuroides Loaded by a Transmembrane pH-Gradient Method

    OpenAIRE

    Zhou, Yan; Wei, Yuhui; Liu, Huanxiang; Zhang, Guoqiang; Wu, Xin’an

    2010-01-01

    A novel transmembrane pH gradient active loading method to prepare alkaloids binary ethosomes was developed in this work. Using this novel method, binary ethosomes containing total alkaloids extracted from Sophora alopecuroides (TASA) were prepared successfully at the temperature below the phase transition temperature (Tc) of the phosphatidyl choline (PC). Several factors affecting this method were investigated. The qualities of the TASA binary ethosomes were characterized by the shape, parti...

  17. Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins

    Directory of Open Access Journals (Sweden)

    Yasufumi Wada

    2010-04-01

    Full Text Available Manynatural products with biologically interesting structures have been isolated from marine animals and plants such as sponges, corals, worms, etc. Some of them are discorhabdin alkaloids. The discorhabdin alkaloids (discorhabdin A-X, isolated from marine sponges, have a unique structure with azacarbocyclic spirocyclohexanone and pyrroloiminoquinone units. Due to their prominent potent antitumor activity, discorhabdins have attracted considerable attention. Many studies have been reported toward the synthesis of discorhabdins. We have accomplished the first total synthesis of discorhabdin A (1, having the strongest activity in vitro among discorhabdins in 2003. In 2009, we have also accomplished the first total synthesis of prianosin B (2, having the 16,17-dehydropyrroloiminoquinone moiety, by a novel dehydrogenation reaction with a catalytic amount of NaN3. These synthetic studies, as well as syntheses of the discorhabdins by various chemists to-date, are reviewed here.

  18. Alkaloids Isolated from Natural Herbs as the Anticancer Agents

    Directory of Open Access Journals (Sweden)

    Jin-Jian Lu

    2012-01-01

    Full Text Available Alkaloids are important chemical compounds that serve as a rich reservoir for drug discovery. Several alkaloids isolated from natural herbs exhibit antiproliferation and antimetastasis effects on various types of cancers both in vitro and in vivo. Alkaloids, such as camptothecin and vinblastine, have already been successfully developed into anticancer drugs. This paper focuses on the naturally derived alkaloids with prospective anticancer properties, such as berberine, evodiamine, matrine, piperine, sanguinarine, and tetrandrine, and summarizes the mechanisms of action of these compounds. Based on the information in the literature that is summarized in this paper, the use of alkaloids as anticancer agents is very promising, but more research and clinical trials are necessary before final recommendations on specific alkaloids can be made.

  19. Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum.

    Science.gov (United States)

    Nissanka, A P; Karunaratne, V; Bandara, B M; Kumar, V; Nakanishi, T; Nishi, M; Inada, A; Tillekeratne, L M; Wijesundara, D S; Gunatilaka, A A

    2001-04-01

    Two benzophenanthrene alkaloids, 8-acetonyldihydronitidine and 8-acetonyldihydroavicine were isolated from Zanthoxylum tetraspermum stem bark along with liriodenine, sesamin, lichexanthone and (+)-piperitol-gamma,gamma-dimethylallylether. The species endemic to Sri Lanka, Z. caudatum, contained sesamin, savinin, liriodenine, decarine and 8-O-desmethyl-N-nornitidine. 8-Acetonyldihydronitidine and 8-acetonyldihydroavicine showed significant antibacterial activity while the former along with liriodenine was strongly antifungal. Savinin exhibited potent spermicidal activity. Both savinin and sesamin exhibited significant insecticidal activity. PMID:11324918

  20. Synthesis studies on the Melodinus alkaloid meloscine

    OpenAIRE

    Feldman, Ken S.; Antoline, Joshua F.

    2013-01-01

    The pentacyclic Melodinus alkaloid (±)-meloscine was synthesized in 19 chemical steps from 2-bromobenzaldehyde through a route featuring an allenyl azide cyclization cascade to deliver the core azabicyclo[3.3.0]octane substructure. Peripheral functionalization of this core included a Tollens-type aldol condensation to set the quaternary center at C(20) and a diastereoselective ring closing metathesis to forge the tetrahydropyridine ring.

  1. A new alkaloid from Solanum cathayanum

    Institute of Scientific and Technical Information of China (English)

    Fan Cheng; Xiang Li; Jun Zhi Wang

    2008-01-01

    A new alkaloid compound I was obtained from Solanum cathayanum, a folk medicine of Hubei Province, together with a knownalkaloid, orotic acid ethyl ester. On the basis of spectroscopic data and chemical methods, I was identified as 8-hydroxy-3-methoxy-5H-pyrido[2,1-c]pyrazin-5-one. Compound 1 can inhibit the production of NO in peritoneal macrophage of mice induced with LPS.The content of NO was determined by enzyme methods.

  2. Potential antimalarial activity of indole alkaloids

    OpenAIRE

    Frederich, Michel; Tits, Monique; Angenot, Luc

    2008-01-01

    New antimalarial treatments are now urgently required, following the emergence of resistance to the most used drugs. Natural products contribute greatly to the therapeutic arsenal in this area, including artemisinin and quinine (and atovaquone, semi-synthetic). Among the natural products, indole alkaloids represent an interesting class of compounds. Screening carried out to date has revealed several substances active in vitro under the micromolar range and with a good selectivity index. This ...

  3. A new diketopiperazine alkaloid from Aspergillus oryzae.

    Science.gov (United States)

    Shaaban, Mohamed; El-Metwally, Mohammad Magdy; Nasr, Hamdi

    2014-01-01

    Investigation of bioactive secondary metabolites from terrestrial Aspergillus oryzae sp. MMAO1 using M2 medium afforded a new diketopiperazine alkaloid, 7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione (1a), containing the unusual amino acid L-6,8-dihydroxy-7-methoxyphenylalanine. This was co-isolated with ditryptophenaline (2), cyclo-(Tryp,Tyr) (4), cyclo-(Pro,Val), α-cyclopiazonic acid (3), kojic acid and uridine. Re-cultivation of the fungal strain on Dox medium led to the production of bisdethio(bismethylthio)gliotoxin (5), pseurotin A (6) along with linoleic acid, α-cyclopiazonic acid (3) and kojic acid. The chemical structure of the new diketopiperazine alkaloid including the relative configuration was determined by 1D and 2D NMR spectroscopy and HR-ESI-MS spectrometry, and by comparison with the related literature. The new alkaloid (1a) showed no antimicrobial activity or cytotoxicity against brine shrimps.

  4. Two New Alkaloids from Roots of Stemona tuberosa

    Directory of Open Access Journals (Sweden)

    Ligen Lin

    2014-07-01

    Full Text Available The roots of Stemona tuberosa ha ve been used as an antitussive and insecticide remedy for thousands of years. On the chemical investigation of the roots of S . tuberosa , two new tuberostemonine-type alkaloids, epoxy-tuberostemonol (1, and neotuberostemoenone (2, together with a known alkaloid, n eotuberostemonine, were isolated and identified. The structures of new alkaloids were established on the basis of 1D and 2D NMR and other spectroscopic analyses.

  5. 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.

  6. New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

    OpenAIRE

    Alois Plodek; Franz Bracher

    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...

  7. A new monoterpenoid oxindole alkaloid from Hamelia patens micropropagated plantlets.

    Science.gov (United States)

    Paniagua-Vega, David; Cerda-García-Rojas, Carlos M; Ponce-Noyola, Teresa; Ramos-Valdivia, Ana C

    2012-11-01

    Chemical studies on Hamelia patens (Rubiaceae) micropropagated plantlets allowed production of a new monoterpenoid oxindole alkaloid, named (-)-hameline (7), together with eight known alkaloids, tetrahydroalstonine (1), aricine (2), pteropodine (3), isopteropodine (4), uncarine F (5), speciophylline (6), palmirine (8), and rumberine (9). The structure of the new alkaloid was assigned on the basis of 1D and 2D NMR spectroscopy, mass spectrometry, and molecular modeling.

  8. Absolute configuration, stability, and interconversion of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine valine adducts and their phenylthiohydantoin derivatives

    Directory of Open Access Journals (Sweden)

    Xiao Jiang

    2015-06-01

    Full Text Available Pyrrolizidine alkaloid-containing plants are widespread in the world and probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids require metabolic activation to form dehydropyrrolizidine alkaloids that bind to cellular proteins and DNA leading to hepatotoxicity, genotoxicity, and tumorigenicity. At present, it is not clear how dehydropyrrolizidine alkaloids bind to cellular amino acids and proteins to induced toxicity. We previously reported that reaction of dehydromonocrotaline with valine generated four highly unstable 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP-derived valine (DHP-valine adducts that upon reaction with phenyl isothiocyanate (PITC formed four DHP-valine-PITC adduct isomers. In this study, we report the absolute configuration and stability of DHP-valine and DHP-valine-PITC adducts, and the mechanism of interconversion between DHP-valine-PITC adducts.

  9. Binding Parameters of Alkaloids Berberine and Sanguinarine with DNA

    CERN Document Server

    Gumenyuk, V G; Kutovyy, S Yu; Yashchuk, V M; Zaika, L A

    2012-01-01

    We study the interaction of berberine and sanguinarine (plant alkaloids) with DNA in aqueous solutions, by using optical spectroscopy methods (absorption and fluorescence). The dependencies of alkaloid spectral characteristics on the concentration ratio N/c between the DNA base pairs and alkaloid molecules in the solutions are considered, and the manifestations of the alkaloid-DNA binding are revealed. The character of binding is found to depend on N/c. The parameters of the binding of berberine and sanguinarine with DNA are determined, by using the modified Scatchard and McGhee-von Hippel equations

  10. Evaluation of Biosynthetic Pathway and Engineered Biosynthesis of Alkaloids.

    Science.gov (United States)

    Kishimoto, Shinji; Sato, Michio; Tsunematsu, Yuta; Watanabe, Kenji

    2016-01-01

    Varieties of alkaloids are known to be produced by various organisms, including bacteria, fungi and plants, as secondary metabolites that exhibit useful bioactivities. However, understanding of how those metabolites are biosynthesized still remains limited, because most of these compounds are isolated from plants and at a trace level of production. In this review, we focus on recent efforts in identifying the genes responsible for the biosynthesis of those nitrogen-containing natural products and elucidating the mechanisms involved in the biosynthetic processes. The alkaloids discussed in this review are ditryptophenaline (dimeric diketopiperazine alkaloid), saframycin (tetrahydroisoquinoline alkaloid), strictosidine (monoterpene indole alkaloid), ergotamine (ergot alkaloid) and opiates (benzylisoquinoline and morphinan alkaloid). This review also discusses the engineered biosynthesis of these compounds, primarily through heterologous reconstitution of target biosynthetic pathways in suitable hosts, such as Escherichia coli, Saccharomyces cerevisiae and Aspergillus nidulans. Those heterologous biosynthetic systems can be used to confirm the functions of the isolated genes, economically scale up the production of the alkaloids for commercial distributions and engineer the biosynthetic pathways to produce valuable analogs of the alkaloids. In particular, extensive involvement of oxidation reactions catalyzed by oxidoreductases, such as cytochrome P450s, during the secondary metabolite biosynthesis is discussed in details. PMID:27548127

  11. New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

    Science.gov (United States)

    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. This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades. PMID:26821033

  12. Evaluation of Biosynthetic Pathway and Engineered Biosynthesis of Alkaloids

    Directory of Open Access Journals (Sweden)

    Shinji Kishimoto

    2016-08-01

    Full Text Available Varieties of alkaloids are known to be produced by various organisms, including bacteria, fungi and plants, as secondary metabolites that exhibit useful bioactivities. However, understanding of how those metabolites are biosynthesized still remains limited, because most of these compounds are isolated from plants and at a trace level of production. In this review, we focus on recent efforts in identifying the genes responsible for the biosynthesis of those nitrogen-containing natural products and elucidating the mechanisms involved in the biosynthetic processes. The alkaloids discussed in this review are ditryptophenaline (dimeric diketopiperazine alkaloid, saframycin (tetrahydroisoquinoline alkaloid, strictosidine (monoterpene indole alkaloid, ergotamine (ergot alkaloid and opiates (benzylisoquinoline and morphinan alkaloid. This review also discusses the engineered biosynthesis of these compounds, primarily through heterologous reconstitution of target biosynthetic pathways in suitable hosts, such as Escherichia coli, Saccharomyces cerevisiae and Aspergillus nidulans. Those heterologous biosynthetic systems can be used to confirm the functions of the isolated genes, economically scale up the production of the alkaloids for commercial distributions and engineer the biosynthetic pathways to produce valuable analogs of the alkaloids. In particular, extensive involvement of oxidation reactions catalyzed by oxidoreductases, such as cytochrome P450s, during the secondary metabolite biosynthesis is discussed in details.

  13. Non-aqueous CE-MS of cinchona alkaloids - characterization of a novel CE-ESI-MS interface

    DEFF Research Database (Denmark)

    Hansen, Frederik André; Hansen, Steen Honoré; Petersen, Nickolaj J.

    the composition of alkaloids in Cinchona bark. One common problem for sheatless interfaces for CE-MS has been establishing a stable electric contact at the end of the separation capillary that does not induce band broadening or affect the spray stability. In our device the electric contact is generated through....... Furthermore, the increased conductivity of the buffer in the fracture generates field free pumping of the analytes towards the ESI spray tip. In this study the device was used to analyze the four major alkaloids (diastereomeric pairs of quinine/quinidine and cinchonine/cinchonidine) in Cinchona bark samples...

  14. Chiral modification of platinum: ab initio study of the effect of hydrogen coadsorption on stability and geometry of adsorbed cinchona alkaloids.

    Science.gov (United States)

    Hahn, Konstanze R; Seitsonen, Ari P; Baiker, Alfons

    2015-11-01

    The cinchona alkaloids cinchonidine and cinchonine belong to the most efficient chiral modifiers for the noble metal-catalyzed enantioselective hydrogenation of C=O and C=C bonds. Under reaction conditions these modifiers are coadsorbed on the noble metal surface with hydrogen. Using density functional theory, we studied the effect of coadsorbed hydrogen on the adsorption mode of cinchonidine and cinchonine on a Pt(111) surface at different hydrogen coverages. The theoretical study indicates that the presence of coadsorbed hydrogen affects both the adsorption geometry as well as the stability of the adsorbed cinchona alkaloids. At all hydrogen coverages the cinchona alkaloids are found to be adsorbed via anchoring of the quinoline moiety. In the absence of hydrogen as well as at low hydrogen coverage the quinoline moiety adsorbs nearly parallel to the surface, whereas at higher hydrogen coverage it becomes tilted. Higher hydrogen coverage as well as partial hydrogenation of the quinoline part of the cinchona alkaloid and hydrogen transfer to the C[double bond, length as m-dash]C double bond at 10, 11 position of the quinuclidine moiety destabilize the adsorbed cinchona alkaloid, whereas hydrogen transfer to the nitrogen atom of the quinoline and the quinuclidine moiety stabilizes the adsorbed molecule. The stability as well as the adsorption geometry of the cinchona alkaloids are affected by the coadsorbed hydrogen and are proposed to influence the efficiency of the enantiodifferentiating ability of the chirally modified platinum surface.

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

    International Nuclear Information System (INIS)

    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 (KA) 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

  16. Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus.

    Science.gov (United States)

    Unver, Nehir; Kaya, G Irem; Werner, Christa; Verpoorte, Robert; Gözler, Belkis

    2003-09-01

    A new indole alkaloid, galanthindole, was isolated from Galanthus plicatus ssp. byzantinus (Amaryllidaceae), a plant native to northwestern Turkey. Incorporating a non-fused indole ring, galanthindole may represent the prototype of a new subgroup of the Amaryllidaceae alkaloids. Two other bases, (+)-11-hydroxyvittatine and hordenine, are also reported from the same plant.

  17. Two New Norditerpenoid Alkaloids from Aconitum spicatum Stapf

    Institute of Scientific and Technical Information of China (English)

    Li Ming GAO; Xiao Mei WEI; Li YANG

    2005-01-01

    Two new norditerpenoid alkaloids, spicatine A (1) and spicatine B (2) were isolated from the root of Aconitum spicatum. The new compounds were deduced on the basis of their spectral data (IR, HREIMS, EIMS, 1D, 2D-NMR). This is the first whole report on the isolation of diterpenoid alkaloids from the A. spicatum Stapf.

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

    Energy Technology Data Exchange (ETDEWEB)

    Sun, Yantao [Key Laboratory of Preparation and Applications of Environmentally Friendly Materials (Jilin Normal University), Ministry of Education China, Siping 136000 (China); College of Chemistry, Jilin Normal University, Siping 136000 (China); Peng, Tingting [College of Chemistry, Jilin Normal University, Siping 136000 (China); College of Chemistry, Baicheng Normal University, Baicheng, 130032 (China); Zhao, Lei [Siping Institute for Food and Drug Control, Siping 136000 (China); Jiang, Dayu [Key Laboratory of Preparation and Applications of Environmentally Friendly Materials (Jilin Normal University), Ministry of Education China, Siping 136000 (China); College of Chemistry, Jilin Normal University, Siping 136000 (China); Cui, Yuncheng, E-mail: 1979yanzi@163.com [Key Laboratory of Preparation and Applications of Environmentally Friendly Materials (Jilin Normal University), Ministry of Education China, Siping 136000 (China); College of Chemistry, Jilin Normal University, Siping 136000 (China)

    2014-12-15

    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{sub 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.

  19. 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-mo

  20. Extraction of alkaloids for NMR-based profiling

    DEFF Research Database (Denmark)

    Yilmaz, Ali; Nyberg, Nils; Jaroszewski, Jerzy W.

    2012-01-01

    of the well-known cinchona alkaloids quinine, cinchonine and cinchonidine without any apparent clustering. Signals from analogues were detected but not in substantial amounts. The main variation was related to the absolute amounts of extracted alkaloids, which was attributed to the evolution of the Cinchona...

  1. New monoterpenoid alkaloids from the aerial parts of Uncaria hirsuta.

    Science.gov (United States)

    Jia, Jun-Feng; Zhang, Yuan; Huang, Xiao-Jun; Zhang, Sheng-Yuan; Tian, Hai-Yan; Wang, Lei; Ye, Wen-Cai

    2014-01-01

    To investigate the chemical constituents of medicinal plant Uncaria hirsuta, three new monoterpenoid alkaloids, named hirsutanines A-C (1-3), were isolated. Their structures with absolute configurations were elucidated by means of NMR, X-ray diffraction and CD analysis. Compound 3 was the first dimeric monoterpenoid alkaloid obtained from genus Uncaria. PMID:24684175

  2. Effects of Ergot Alkaloids on Bovine Sperm Motility In Vitro

    Science.gov (United States)

    Ergot alkaloids are synthesized by endophyte-infected (Neotyphodium coenophialum) tall fescue (Lolium arundinaceum (Schreb.) S.J. Darbyshire). Our objective was to determine direct effects of ergot alkaloids (ergotamine, dihydroergotamine and ergonovine) on the motility of bovine spermatozoa in vit...

  3. Significance of saguaro cactus alkaloids in ecology ofDrosophila mettleri, a soil-breeding, cactophilic drosophilid.

    Science.gov (United States)

    Meyer, J M; Fogleman, J C

    1987-11-01

    Drosophila mettleri is a soil-breeding, cactophilic drosophilid which lives in the Sonoran Desert. Several chemical constituents of cacti in this region have been identified as having major roles in insect-host plant relationships involvingDrosophila. For example, isoquinoline alkaloids, which are present in senita cactus, have been shown to be toxic to seven of the nine species tested. The two tolerant species areD. pachea, the normal resident, andD. mettleri. Necroses of senita cacti are often used as feeding substrates byD. mettleri adults, but this species has never been reared from senita rots. Soil, which have been soaked by juice from saguaro and cardón rots, are the typical breeding substrates of this species. The tissues of both of these cacti also contain alkaloids, chemically related to those in senita, but at much lower concentrations. Alkaloid concentration in saguaro-soaked soil was found to be 1.4-27 times the average concentration in fresh tissue. Alkaloids were extracted from saguaro tissue and used in tests of larva-to-adult viability, developmental rate, and adult longevity. Elevated concentrations of saguaro alkaloids had no significant effect on the longevity ofD. mettleri, but significantly reduced the longevity ofD. nigrospiracula andD. mojavensis, two nonsoil breeding cactophilic species. Viability and developmental rates of all three species were affected, but the effect onD. nigrospiracula was comparatively greater. It is argued that the adaptations that allowD. mettleri to utilize the saguaro soil niche also convey tolerance to alkaloids present in senita tissue. The ability to utilize senita necroses as feeding substrates represents an ecological advantage to D. mettleri, in that the density of potential feeding sites is increased as compared to species which are more specific in their host-plant relationships. PMID:24301541

  4. CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW. PART 1- CRINUM ALKALOIDS: LYCORINE-TYPE ALKALOIDS

    Directory of Open Access Journals (Sweden)

    John Refaat*, Mohamed S. Kamel , Mahmoud A. Ramadan and Ahmed A. Ali

    2012-07-01

    Full Text Available Crinum is an important Amaryllidaceous plant thanks to the valuable biological and therapeutic activities of its chemical constituents, especially alkaloids. Many Crinum species have been commonly used in traditional medicines worldwide. Long ago, they have been subjected to extensive chemical, cytological and pharmacological investigations. Accordingly, this work comprehensively comprises both the alkaloidal and non-alkaloidal principles of Crinums isolated from 1950 and up to now, together with various biological and toxicological studies conducted on both the total extracts and individual compounds. As being a major common class of Crinum alkaloids, the current part of this review work highlights the lycorine-type alkaloids isolated so far from this plant in addition to their distribution in different Crinum species.

  5. 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.

  6. Targeted and untargeted profiling of alkaloids in herbal extracts using online solid-phase extraction and high-resolution mass spectrometry (Q-Orbitrap).

    Science.gov (United States)

    Nardin, Tiziana; Piasentier, Edi; Barnaba, Chiara; Larcher, Roberto

    2016-09-01

    The biological activity of alkaloids (ALKs) and the different content of these natural products in herbs and plants have made them an attractive field for chemical studies. A screening method automatically combining online solid-phase purification and concentration of samples with analysis using ultra-high performance liquid chromatography coupled with a hybrid quadrupole orbitrap mass spectrometer was developed and is reported in this paper. The proposed quantification method was validated for 35 ALKs with reference to pure analytical standards. A further 48 ALKs were identified on the basis of their accurate mass and characterised for chromatographic retention time and fragmentation profile, following their confirmation in extracts of herbs already well documented in the literature. More than 250 other untargeted ALKs were also tentatively identified using literature information, such as exact mass and isotopic pattern. The mass spectrometer operated in positive ion mode and mass spectra were acquired, with full MS-data-dependent MS/MS analysis (full MS-dd MS/MS) at a resolution of 140 000. The method was linear up to an ALK concentration of 1000/3000 µg l(-1) , with R(2) always >0.99 and limits of detection ranging between 0.04 and 10 µg l(-1) . Accuracy, expressed as the recovery relative error, had a median value of 7.4%, and precision (relative standard deviation %) was generally lower than 10% throughout the quantitation range. The proposed method was then used to investigate the targeted and untargeted ALK profile of a selection of 18 alpine herbal plants, establishing that pyrrolizidine, pyrrolidine and piperidine ALKs were the most well represented. Copyright © 2016 John Wiley & Sons, Ltd. PMID:27502171

  7. 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)

  8. The distribution of inole alkaloids in different organs of Catharanthus roseus G. Don. (Vinca rosea L)

    OpenAIRE

    Hassan Ebrahimzadeh; Azra Ataei -Azimi4 Mohammad-Reza Noori-Dafoi

    1996-01-01

    The study of alkaloid extract of the leaf of Vinca rosea by TLC showed the existence of 13 bands, 7 bands of them were: Serpentine, Vincristine, Vinblastine, Ajmaline, Catharantine, Vindoline and Ajmalicine. The existence of these 7 alkaloids was confirmed in the young leaves, old leaves and the roots of the plant by HPLC. Furthermore, two alkaloids with the short retention times and one alkaloid with the medium retention time in the young leaf, three alkaloids with the short retention time a...

  9. γ-Lactam alkaloids from the flower buds of daylily.

    Science.gov (United States)

    Matsumoto, Takahiro; Nakamura, Seikou; Nakashima, Souichi; Ohta, Tomoe; Yano, Mamiko; Tsujihata, Junichiro; Tsukioka, Junko; Ogawa, Keiko; Fukaya, Masashi; Yoshikawa, Masayuki; Matsuda, Hisashi

    2016-07-01

    Four new alkaloids, hemerocallisamines IV-VII, were isolated from the methanol extract of flower buds of daylily. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The absolute stereochemistry of the hemerocallisamines IV-VI was elucidated by the application of the modified Mosher's method, HPLC analysis, and optical rotation. In the present study, the isolated alkaloids significantly inhibited the aggregation of Aβ42 in vitro. This is the first report about bioactive alkaloids with a γ-lactam ring from daylily. In addition, isolated nucleosides showed accelerative effects on neurite outgrowth under the non-fasting condition.

  10. 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)

  11. Antifouling Alkaloids from Crinum augustum (Amaryllidaceae

    Directory of Open Access Journals (Sweden)

    John Refaat

    2009-01-01

    Full Text Available Fractionation and purification of the ethanolic extract of the bulbs of Crinum augustum Rox. (Amaryllidaceae cultivated in Egypt yielded five alkaloids 6-methoxy-crinamine (1 , crinamine (2 , buphanisine (3 , ungeremine (4 , and hippadine (5 ; two fatty acid derivatives: myristic acid ethyl ester (6 and palmitic acid ethyl ester (7 ; four terpenoidal and steroidal compounds: ursolic acid (8 , β-sitosterol-O- β glucopyranoside (9 and mixture of β--sitosterol (10 and stigmasterol (11 . The structures of all compounds were determined by interpretation of their spectroscopic data; 1D ( 1 H and 13 C, 2D (HSQC, COSY, DQF, NOE and HMBC NMR; MS and UV analyses. The compounds (1 -4 and (6-8 were tested towards biofouling activity using larvae of barnacle Balance amphitrie. Significant activities of 1, 2 and 3 with EC 50 1.8, 1.2 and 0.75 μg/mL respectively, were observed.

  12. Pyrrolidonyl and pyridyl alkaloids in Lymantria dispar.

    Science.gov (United States)

    Deml, Reinhold

    2003-01-01

    The occurrence and metabolism of nicotine and related N-containing compounds in body fluids of the gipsy moth were addressed. Thin layer chromatographic studies clearly showed the simultaneous presence of GABA and 2-pyrrolidone but not of GABamide in the larval haemolymph and osmeterial secretion of Lymantria dispar as well as in the corresponding body fluids of the saturniids, Saturnia pavonia and Attacus atlas. Furthermore, feeding and injection experiments using alkylated precursors and combined gas chromatography/mass spectrometry gave evidence of the transformation of 2-pyrrolidone to nicotine and of nicotinic acid to nicotinamide in caterpillars of L. dispar. Based on these results, on the earlier described variation of the secondary-compound patterns of L. dispar during its development, and on literature data, metabolic pathways for the hitherto detected pyridyl and pyrrolidonyl alkaloids in Lymantriidae (and possibly Saturniidae) are proposed.

  13. Dietary exposure to ergot alkaloids decreases contractility of bovine mesenteric vasculature.

    Science.gov (United States)

    Egert, A M; Kim, D H; Schrick, F N; Harmon, D L; Klotz, J L

    2014-04-01

    Ergot alkaloids are hypothesized to cause vasoconstriction in the midgut, and prior exposure may affect the vasoactivity of these compounds. The objectives of this study were to profile vasoactivity of ergot alkaloids in bovine mesenteric artery (MA) and vein (MV) and determine if previous exposure to endophyte-infected tall fescue seed affected vasoactivity of ergocryptine (ERP), ergotamine (ERT), ergocristine (ERS), ergocornine (ERO), ergonovine (ERN), lysergic acid (LSA), ergovaline-containing tall fescue seed extract (EXT), and 5-hydroxytryptamine (5HT; serotonin). Ruminally cannulated Angus steers (n = 12; BW = 547 ± 31 kg) were paired by weight and randomly assigned to 6 blocks. Steers were ruminally dosed daily with 1 kg of either endophyte-infected (E+; 4.45 mg ergovaline/kg DM) or endophyte-free (E-; 0 mg ergovaline/kg DM) tall fescue seed for 21 d before slaughter. Branches of MA and MV supporting the cranial portion of the ileum were collected after slaughter on d 22, placed in a modified Krebs-Henseleit buffer on ice, cleaned, sectioned, and mounted in a multimyograph chamber. Contractile response was normalized to a maximum KCl response. Inner diameter (P = 0.04) and outer diameter (P = 0.02) of MA were smaller for E+ steers than E- steers. Maximum contractile responses to 120 mM KCl were not different between seed treatments in MA (P = 0.33; E-: 2.67 ± 0.43 g; E+: 3.33 ± 0.43 g) or MV (P = 0.26; E-: 2.01 ± 0.18 g; E+: 1.81 ± 0.18 g). Steers receiving E+ had a smaller (P < 0.01) MA contractile response than E- steers to ERP, ERT, ERS, ERO, ERN, EXT, and 5HT. Steers receiving E+ had a smaller (P < 0.05) MV contractile response than E- steers to ERP, ERT, ERS, ERN, EXT, and 5HT. Lysergic acid failed to induce a contractile response in MA and MV. The contractile response in MA and MV of E- steers produced by 5HT was very large. The EXT was the most potent (P < 0.05) agonist in MV and MA of E+ steers. These data showed that ergot alkaloids were

  14. Investigation of Aconitine-type Alkaloids from Processed Tuber of Aconitum carmiechaeli by HPLC-ESI-MS/MSn

    Institute of Scientific and Technical Information of China (English)

    YUE Hao; PI Zi-feng; ZHAO Yu-feng; SONG Feng-rui; LIU Zhi-qiang; LIU Shu-ying

    2007-01-01

    @@ Introduction Aconitine-type alkaloids isolated from the roots of Aconitum carmiechaeli show a potential toxicity and a broad spectrum of bioactivity[1-4]. On the basis of the C8-substituent of C19-diterpenoid skeleton, aconitinetype alkaloids can be divided into diester-diterpenoid alkaloids( DDAs), monoester-diterpenoid alkaloids(MDAs), and lipo-alkaloids( Fig. 1 ).

  15. Physiological responses to known intake of ergot alkaloids by steers at environmental temperatures within or greater than their thermoneutral zone

    Science.gov (United States)

    Eisemann, Joan; Huntington, Gerald; Williamson, Megan; Hanna, Michelle; Poore, Matthew

    2014-11-01

    Two studies separated effects of dietary ergot alkaloids from effects of feed intake or ambient temperature on respiration rate (RR), heart rate (HR), surface temperature (ST), rectal temperature (RT), blood pressure (BP), serum hormone, and plasma metabolite concentrations in beef steers. The balanced, single reversal design for each experiment used 8 beef steers fed tall fescue seed (2.5 g/kg body weight, (BW)) with (E+) or without (E-) ergot alkaloids as part of a 60:40 switchgrass hay: supplement diet. Periods were 35 d with 21 d of preliminary phase and 14 d of feeding fescue seed once daily. Measures of dependent variables were collected on d 20, 25, 29 and 35 of each period at 0730 (before feeding), 1230 and 1530. In Expt 1 steers weighed 286 kg, gained 0.61 kg BW/d, E+ supplied 2.72 mg ergot alkaloids including 1.60 mg ergovaline per steer daily, and mean minimum and maximum daily ambient temperatures were 23.6 and 32.3°C. In Expt 2 steers weighed 348 kg, gained 1.03 kg BW/d, E+ supplied 3.06 mg ergot alkaloids including 2.00 mg ergovaline daily, and mean minimum and maximum daily ambient temperatures were 11.9 and 17.4°C. Dry matter intake was not affected by fescue seed treatment (P zone, E+ increased (Pzone, E+ and E- did not differ (P zone to exacerbate the symptoms of hyperthermic stress.

  16. A New Binary Carbazole Alkaloid from Murraya koenigii

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    A new binary carbazole alkaloid, 8, 8"-biskoenigine (1), along with its monomer,kocnigine, was isolated from the dried leaves of Murraya koenigii collected in Xishuangbanna,Yunnan province. The structure of 1 was established by spectroscopic methods.

  17. Total synthesis, biosynthesis and biological profiles of clavine alkaloids.

    Science.gov (United States)

    McCabe, Stephanie R; Wipf, Peter

    2016-07-01

    This review highlights noteworthy synthetic and biological aspects of the clavine subfamily of ergot alkaloids. Recent biosynthetic insights have laid the groundwork for a better understanding of the diverse biological pathways leading to these indole derivatives. Ergot alkaloids were among the first fungal-derived natural products identified, inspiring pharmaceutical applications in CNS disorders, migraine, infective diseases, and cancer. Pergolide, for example, is a semi-synthetic clavine alkaloid that has been used to treat Parkinson's disease. Synthetic activities have been particularly valuable to facilitate access to rare members of the Clavine family and empower medicinal chemistry research. Improved molecular target identification tools and a better understanding of signaling pathways can now be deployed to further extend the biological and medical utility of Clavine alkaloids. PMID:27215547

  18. 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...

  19. A new pyrrole alkaloid from seeds of Castanea sativa.

    Science.gov (United States)

    Hiermann, Alois; Kedwani, Samir; Schramm, Hans Wolfgang; Seger, Christoph

    2002-02-01

    A new pyrrole alkaloid, methyl-(5-formyl-1H-pyrrole-2-yl)-4-hydroxybutyrate (1), was isolated from sweet chestnut seeds and its structure elucidated on the basis of data from NMR spectroscopy and by comparison with synthetic analogues.

  20. NEW NORDITERPENOID ALKALOIDS FROM THE ROOTS OF ACONITUM GENICULATUM

    Institute of Scientific and Technical Information of China (English)

    ZHENG-BANG LI; LIANG XU; XI-XIAN JIAN; FENG-PENG WANG

    2001-01-01

    Four new norditerpenoid alkaloids, geniculatines A (1), B (4), C (7) and D (8), were isolated from the roots of Aconitum geniculatum Fletcher, and their structures were elucidated by spectral methods.

  1. Marine bromopyrrole alkaloids: synthesis and diverse medicinal applications.

    Science.gov (United States)

    Rane, Rajesh; Sahu, Niteshkumar; Shah, Chetan; Karpoormath, Rajshekhar

    2014-01-01

    Marine organisms have been found to be a very rich source of bioactive molecules. Among marine organisms, sponges have been proven to be excellent producers of secondary metabolites. More than 5,300 compounds have been isolated from sponges with around 200 new molecules reported each year. Bromopyrrole alkaloids constitute a family of exclusively marine alkaloids and represent a fascinating example of the large variety of compounds formed by marine sponges which exhibit different biological activities such as antifeedent, anti-biofilm, anticancer, antiinflammatory, antimicrobial, immunomodulatory, analgesic, antiserotonergic, antiangiogenic, antihistaminic, chitinase inhibitor and actimyosin ATPase activator. More than 140 derivatives with different structures and biological activities, have been isolated from more than 20 different sponges. Most of these alkaloids share a key building block, pyrrole-imidazole with oroidin being their underlying structural motif. In this review detailed account of isolation and medicinal application of marine bromopyrrole alkaloids and their synthetic derivatives are discussed. PMID:24359195

  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.

    The sponge Psammaplysilla purpurea (Order: Verongidae, Family: Aplysinellidae) is a well known source for several bromotyrosine alkaloids of unique structural features and exhibiting promising biological activities such as cytotoxicity...

  3. 3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens.

    OpenAIRE

    S. C. Liu; Oguntimein, B; Hufford, C D; Clark, A M

    1990-01-01

    Further examination of the active ethanolic extract of the root bark of Cleistopholis patens by using bioassay-directed fractionation resulted in the isolation of a new alkaloid, 3-methoxysampangine (compound I), together with three known alkaloids, eupolauridine (compound II), liriodenine (compound III), and eupolauridine N-oxide (compound IV). The proposed structure of compound I was based on its physicochemical properties and spectral data. 3-Methoxysampangine exhibited significant antifun...

  4. Initial Studies on Alkaloids from Lombok Medicinal Plants

    OpenAIRE

    John B. Bremner; Surya Hadi

    2001-01-01

    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 ...

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

    OpenAIRE

    Nikolić Milan; Đorđević Siniša M.

    2003-01-01

    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 ...

  6. Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives.

    Science.gov (United States)

    Gaziano, Roberta; Moroni, Gabriella; Buè, Cristina; Miele, Martino Tony; Sinibaldi-Vallebona, Paola; Pica, Francesca

    2016-01-15

    Historically, natural products have represented a significant source of anticancer agents, with plant-derived drugs becoming increasingly explored. In particular, sanguinarine is a benzophenanthridine alkaloid obtained from the root of Sanguinaria canadensis, and from other poppy Fumaria species, with recognized anti-microbial, anti-oxidant and anti-inflammatory properties. Recently, increasing evidence that sanguinarine exibits anticancer potential through its capability of inducing apoptosis and/or antiproliferative effects on tumor cells, has been proved. Moreover, its antitumor seems to be due not only to its pro-apoptotic and inhibitory effects on tumor growth, but also to its antiangiogenic and anti-invasive properties. Although the precise mechanisms underlying the antitumor activity of this compound remain not fully understood, in this review we will focus on the most recent findings about the cellular and molecular pathways affected by sanguinarine, together with the rationale of its potential application in clinic. The complex of data currently available suggest the potential application of sanguinarine as an adjuvant in the therapy of cancer, but further pre-clinical studies are needed before such an antitumor strategy can be effectively translated in the clinical practice. PMID:26798435

  7. Anticholinesterase inhibitory activity of quaternary alkaloids from Tinospora crispa.

    Science.gov (United States)

    Yusoff, Mashitah; Hamid, Hazrulrizawati; Houghton, Peter

    2014-01-01

    Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids-dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-formylannonaine (5), N-formylnornuciferine (6), and N-trans-feruloyltyramine (7). The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman's method. In the AChE inhibition assay, only columbamine (3) showed strong activity with IC50 48.1 µM. The structure-activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition. PMID:24448061

  8. The Interference of Selected Cytotoxic Alkaloids with the Cytoskeleton: An Insight into Their Modes of Action.

    Science.gov (United States)

    Wang, Xiaojuan; Tanaka, Mine; Krstin, Sonja; Peixoto, Herbenya Silva; Wink, Michael

    2016-01-01

    Alkaloids, the largest group among the nitrogen-containing secondary metabolites of plants, usually interact with several molecular targets. In this study, we provide evidence that six cytotoxic alkaloids (sanguinarine, chelerythrine, chelidonine, noscapine, protopine, homoharringtonine), which are known to affect neuroreceptors, protein biosynthesis and nucleic acids, also interact with the cellular cytoskeleton, such as microtubules and actin filaments, as well. Sanguinarine, chelerythrine and chelidonine depolymerized the microtubule network in living cancer cells (Hela cells and human osteosarcoma U2OS cells) and inhibited tubulin polymerization in vitro with IC50 values of 48.41 ± 3.73, 206.39 ± 4.20 and 34.51 ± 9.47 μM, respectively. However, sanguinarine and chelerythrine did not arrest the cell cycle while 2.5 μM chelidonine arrested the cell cycle in the G₂/M phase with 88.27% ± 0.99% of the cells in this phase. Noscapine and protopine apparently affected microtubule structures in living cells without affecting tubulin polymerization in vitro, which led to cell cycle arrest in the G2/M phase, promoting this cell population to 73.42% ± 8.31% and 54.35% ± 11.26% at a concentration of 80 μM and 250.9 μM, respectively. Homoharringtonine did not show any effects on microtubules and cell cycle, while the known microtubule-stabilizing agent paclitaxel was found to inhibit tubulin polymerization in the presence of MAPs in vitro with an IC50 value of 38.19 ± 3.33 μM. Concerning actin filaments, sanguinarine, chelerythrine and chelidonine exhibited a certain effect on the cellular actin filament network by reducing the mass of actin filaments. The interactions of these cytotoxic alkaloids with microtubules and actin filaments present new insights into their molecular modes of action. PMID:27420038

  9. Analysis of Norditerpenoid Alkaloids Extracted from Aconitum sinomantanum Nakai by Electrospray Ionization Tandem Mass Spectrometry

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    Electrospray ionization mass spectrometry(ESI-MS) was applied simultaneously in determining norditerpenoid alkaloids from the roots of Aconitum sinomantanum Nakai (RAS) based on molecular mass information. The tandem mass spectra(ESI-MSn) provided the alkaloidal structural information, through which the existence of these alkaloids was further confirmed. Accordingly, six known norditerpenoid alkaloids were simultaneously determined on the basis of their ESI-MSn spectra. Furthermore, based on the diagnostic fragmentation pathways of alkaloidal MSn, a rapid method for direct detection and characterization of alkaloids from an ethanolic extract of RAS was described.

  10. 九里明抗菌镇痛有效部位中PAs的研究%Studies on Pyrrolizidine Alkaloids in Antimicrobial and Analgesic Part Extracted from Senecio Scandens

    Institute of Scientific and Technical Information of China (English)

    陈进军; 聂芳红; 赵生才; 林红英; 李明伟; 马驿; 徐晓彬; 冯羽裳

    2006-01-01

    采用试管分项提取预试法、系统提取预试法和圆形纸层析预试法,进行了九里明植物化学成分预试;利用硅胶G薄板层析法,Ehrlich试剂喷雾显色,对九里明全草及其抗菌镇痛有效部位中双稠吡咯啶生物碱进行了检查.结果发现,九里明全草含有黄酮及其甙类、蒽醌及其甙类、酚类、强心甙、氨基酸、鞣质、皂甙、有机酸和生物碱,不含氰甙、多肽、蛋白质、内酯、油脂和挥发油;九里明全草含有双稠吡咯啶生物碱,但九里明抗菌镇痛有效部位中则未检出双稠吡咯啶生物碱.

  11. Effects of Ergot Alkaloids on Liver Function of Piglets as Evaluated by the 13C-Methacetin and 13C-α-Ketoisocaproic Acid Breath Test

    Directory of Open Access Journals (Sweden)

    Sonja Diers

    2013-01-01

    Full Text Available Ergot alkaloids (the sum of individual ergot alkaloids are termed as total alkaloids, TA are produced by the fungus Claviceps purpurea, which infests cereal grains commonly used as feedstuffs. Ergot alkaloids potentially modulate microsomal and mitochondrial hepatic enzymes. Thus, the aim of the present experiment was to assess their effects on microsomal and mitochondrial liver function using the 13C-Methacetin (MC and 13C-α-ketoisocaproic acid (KICA breath test, respectively. Two ergot batches were mixed into piglet diets, resulting in 11 and 22 mg (Ergot 5-low and Ergot 5-high, 9 and 14 mg TA/kg (Ergot 15-low and Ergot 15-high and compared to an ergot-free control group. Feed intake and live weight gain decreased significantly with the TA content (p < 0.001. Feeding the Ergot 5-high diet tended to decrease the 60-min-cumulative 13CO2 percentage of the dose recovery (cPDR60 by 26% and 28% in the MC and KICA breath test, respectively, compared to the control group (p = 0.065. Therefore, both microsomal and mitochondrial liver function was slightly affected by ergot alkaloids.

  12. Total synthesis of the indolizidine alkaloid tashiromine

    Directory of Open Access Journals (Sweden)

    McElhinney Alison D

    2008-01-01

    Full Text Available Abstract Background Tashiromine 1 is a naturally occurring indolizidine alkaloid. It has been the subject of thirteen successful total syntheses to date. Our own approach centres on the stereoselective construction of the indolizidine core by capture of an electrophilic acyliminium species by a pendant allylsilane. The key cyclisation precursor is constructed using olefin cross-metathesis chemistry, which has the potential to facilitate both racemic and asymmetric approaches, depending upon the choice of the allylsilane metathesis partner. Results The use of the allyltrimethylsilane cross-metathesis approach enables the rapid construction of the key cyclisation precursor 3 (3 steps from commercial materials, which undergoes acid-induced cyclisation to give the desired bicyclic indolizidine skeleton as a 96:4 mixture of diastereomers. Simple functional group interconversions allowed the completion of the total synthesis of racemic tashiromine in six steps (19% overall yield. Three chiral α-alkoxyallylsilanes (12,14 and 15 were prepared in enantioenriched form and their cross-metathesis reactions studied as part of a putative asymmetric approach to tashiromine. In the event, α-hydroxysilane 12 underwent isomerisation under the reaction conditions to acylsilane 17, while silanes 14 and 15 were unreactive towards metathesis. Conclusion A concise, stereoselective total synthesis of racemic tashiromine has been developed. Attempts to translate this into an asymmetric synthesis have thus far been unsuccessful.

  13. Alkaloids and athlete immune function: caffeine, theophylline, gingerol, ephedrine, and their congeners.

    Science.gov (United States)

    Senchina, David S; Hallam, Justus E; Kohut, Marian L; Nguyen, Norah A; Perera, M Ann d N

    2014-01-01

    Plant alkaloids are found in foods, beverages, and supplements consumed by athletes for daily nutrition, performance enhancement, and immune function improvement. This paper examined possible immunomodulatory roles of alkaloids in exercise contexts, with a focus on human studies. Four representative groups were scrutinized: (a) caffeine (guaranine, mateine); (b) theophylline and its isomers, theobromine and paraxanthine; (c) ginger alkaloids including gingerols and shogaol; and (d) ephedra alkaloids such as ephedrine and pseudoephedrine. Emerging or prospective alkaloid sources (Goji berry, Noni berry, and bloodroot) were also considered. Human in vitro and in vivo studies on alkaloids and immune function were often conflicting. Caffeine may be immunomodulatory in vivo depending on subject characteristics, exercise characteristics, and immune parameters measured. Caffeine may exhibit antioxidant capacities. Ginger may exert in vivo anti-inflammatory effects in certain populations, but it is unclear whether these effects are due to alkaloids or other biochemicals. Evidence for an immunomodulatory role of alkaloids in energy drinks, cocoa, or ephedra products in vivo is weak to nonexistent. For alkaloid sources derived from plants, variability in the reviewed studies may be due to the presence of unrecognized alkaloids or non-alkaloid compounds (which may themselves be immunomodulatory), and pre-experimental factors such as agricultural or manufacturing differences. Athletes should not look to alkaloids or alkaloid-rich sources as a means of improving immune function given their inconsistent activities, safety concerns, and lack of commercial regulation. PMID:24974722

  14. Bioactivity Studies of β-Lactam Derived Polycyclic Fused Pyrroli-Dine/Pyrrolizidine Derivatives in Dentistry: In Vitro, In Vivo and In Silico Studies.

    Directory of Open Access Journals (Sweden)

    Gowri Meiyazhagan

    Full Text Available The antibacterial activity of β-lactam derived polycyclic fused pyrrolidine/pyrrolizidine derivatives synthesized by 1, 3-dipolar cycloaddition reaction was evaluated against microbes involved in dental infection. Fifteen compounds were screened; among them compound 3 showed efficient antibacterial activity in an ex vivo dentinal tubule model and in vivo mice infectious model. In silico docking studies showed greater affinity to penicillin binding protein. Cell damage was observed under Scanning Electron Microscopy (SEM which was further proved by Confocal Laser Scanning Microscope (CLSM and quantified using Flow Cytometry by PI up-take. Compound 3 treated E. faecalis showed ROS generation and loss of membrane integrity was quantified by flow cytometry. Compound 3 was also found to be active against resistant E. faecalis strains isolated from failed root canal treatment cases. Further, compound 3 was found to be hemocompatible, not cytotoxic to normal mammalian NIH 3T3 cells and non mutagenic. It was concluded that β-lactam compound 3 exhibited promising antibacterial activity against E. faecalis involved in root canal infections and the mechanism of action was deciphered. The results of this research can be further implicated in the development of potent antibacterial medicaments with applications in dentistry.

  15. Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa

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    Mashitah Yusoff

    2014-01-01

    Full Text Available Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1, along with six known alkaloids—dihydrodiscretamine (2, columbamine (3, magnoflorine (4, N-formylannonaine (5, N-formylnornuciferine (6, and N-trans-feruloyltyramine (7. The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman’s method. In the AChE inhibition assay, only columbamine (3 showed strong activity with IC50 48.1 µM. The structure–activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition.

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

    International Nuclear Information System (INIS)

    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 IC50 values ranging from 0.3 to 11.6 μM 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 IC50 50 < 10 μM. 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)

  17. 6,7-diepicastanospermine, a tetrahydroxyindolizidine alkaloid inhibitor of amyloglucosidase

    Energy Technology Data Exchange (ETDEWEB)

    Molyneux, R.J.; Benson, M. (Dept. of Agriculture, Albany, CA (United States)); Pan, Y.T.; Tropea, J.E.; Kaushal, G.P.; Elbein, A.D. (Univ. of Texas, San Antonio (United States))

    1991-10-15

    A tetrahydroxyindolizidine alkaloid, 6,7-diepicastanospermine, was isolated from the seeds of Castanospermum australe by extraction with methanol and purified to homogeneity using ion-exchange, preparative thin-layer, and radial chromatography. A very low yield of a pyrrolidine alkaloid, N-(hydroxyethyl)-2-(hydroxymethyl)-3-hydroxypyrrolidine, was also obtained by analogous methods. The purity of both alkaloids was established by gas chromatography of their trimethylsilyl (TMS) derivatives as better than 99%. The molecular weight of each alkaloid was established as 189 and 161, respectively, by mass spectrometry, and the structure of each was deduced from their {sup 1}H and {sup 13}C NMR spectra. The structure of the pyrrolidine alkaloids which co-occur in C. australe. 6,7-Diepicastanospermine was found to be a moderately good inhibitor of the fungal {alpha}-glucosidase, amyloglucosidase and a relatively weak inhibitor of {beta}-glucosidase. It failed to inhibit {alpha}-glucosidase. It failed to inhibit {alpha}- or {beta}-galactosidase, {alpha}- or {beta}-mannosidase, or {alpha}-L-fucosidase. Comparison of its inhibitory activity toward amyloglucosidase with those of its isomers, castanospermine and 6-epicastanospermine, demonstrated that epimerization of a single hydroxyl group can produce significant alteration of such inhibitory properties.

  18. Alkaloids of the Annonaceae: occurrence and a compilation of their biological activities.

    Science.gov (United States)

    Lúcio, Ana Silvia Suassuna Carneiro; Almeida, Jackson Roberto Guedes da Silva; Da-Cunha, Emídio Vasconcelos Leitão; Tavares, Josean Fechine; Barbosa Filho, Jos Maria

    2015-01-01

    This chapter presents an overview of the chemistry and pharmacology of the alkaloids found in species of the Annonaceae family. The occurrence of alkaloids from Annonaceae species, as well as their chemical structures and pharmacological activities are summarized in informative and easy-to-understand tables. Within the Annonaceae family, the genera Annona, Duguetia, and Guatteria have led to many important publications. Valuable and comprehensive information about the structure of these alkaloids is provided. The alkaloids of the aporphine type represent the predominant group in this family. Many of the isolated alkaloids exhibit unique structures. In addition to the chemical structures, the pharmacological activities of some alkaloids are also presented in this chapter. Thus, the leishmanicidal, antimicrobial, antitumor, cytotoxic, and antimalarial activities observed for these alkaloids are highlighted. The chapter is presented as a contribution for the scientific community, mainly to enable the search for alkaloids in species belonging to the Annonaceae family.

  19. Physiological responses to known intake of ergot alkaloids by steers at environmental temperatures within or greater than their thermoneutral zone

    Directory of Open Access Journals (Sweden)

    Joan eEisemann

    2014-11-01

    Full Text Available Two studies separated effects of dietary ergot alkaloids from effects of feed intake or ambient temperature on respiration rate (RR, heart rate (HR, surface temperature (ST, rectal temperature (RT, blood pressure (BP, serum hormone, and plasma metabolite concentrations in beef steers. The balanced, single reversal design for each experiment used 8 beef steers fed tall fescue seed (2.5 g/kg body weight, (BW with (E+ or without (E- ergot alkaloids as part of a 60:40 switchgrass hay: supplement diet. Periods were 35 d with 21 d of preliminary phase and 14 d of feeding fescue seed once daily. Measures of dependent variables were collected on d 20, 25, 29 and 35 of each period at 0730 (before feeding, 1230 and 1530. In Expt 1 steers weighed 286 kg, gained 0.61 kg BW/d, E+ supplied 2.72 mg ergot alkaloids including 1.60 mg ergovaline per steer daily, and mean minimum and maximum daily ambient temperatures were 23.6 and 32.3°C. In Expt 2 steers weighed 348 kg, gained 1.03 kg BW/d, E+ supplied 3.06 mg ergot alkaloids including 2.00 mg ergovaline daily, and mean minimum and maximum daily ambient temperatures were 11.9 and 17.4°C. Dry matter intake was not affected by fescue seed treatment (P < 0.20 in either experiment. In both experiments, E+ reduced HR (P < 0.01 and increased insulin (P = 0.07. Systolic BP minus diastolic BP decreased (P< 0.05 for E+ in both experiments, due to increased diastolic BP in Expt 1 (P < 0.03 and decreased systolic BP in Expt 2 (P < 0.07. In Expt 1, above the thermoneutral zone, E+ increased (P< 0.05 RR, RT and left side ST in comparison to E-, but in Expt 2, within the thermoneutral zone, E+ and E- did not differ (P < 0.18. Ergot alkaloids from fescue seed affect the cardiovascular system of steers separately from effects of feed intake or environmental temperature. Ergot alkaloids interact with ambient temperatures above the steers’ thermoneutral zone to exacerbate the symptoms of hyperthermic stress.

  20. Solid substrate mediated changes in ergot alkaloid spectra in solid state fermentation system

    OpenAIRE

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

    1993-01-01

    Use of different solid substrates resulted in minor alterations in total alkaloid production by #Claviceps purpurea$ 1029c in solid state fermentation system but the changes in the spectra of ergot alkaloids were of significantly higher magnitudes. Ergonovine accounted for 93% of the total alkaloid production in wheat grain medium while lysergic acid derivatives and ergonovine comprised of 66% and 32% of total alkaloids in rye grain medium. In contrast, ergonovine, ergotamine, and lysergic ac...

  1. 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

  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...... alkaloid was prepared from antirrhinoside by means of an enzymatic cleavage to afford the aglucone, followed by a double reductive amination with benzylamine hydrochloride and sodium cyanoborohydride. The resulting piperidine was modified by opening of the epoxide on the cyclopropane ring by azide...... strategy was therefore abandoned.A one-pot reaction involving ozonolysis and subsequent reduction of the 5,6-O-isopropylidene-2',3',4',6'-tetra-O-acetyl antirrhinoside yielded a diol, which was considered a potential intermediate in the preparation of enantiopure 3-azabicyclo[3.3.0]octane alkaloids...

  3. Terpenoid Indole Alkaloids Biosynthesis and Metabolic Engineering in Catharanthus roseus

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Catharanthus roseus L. (Madagascar periwinkle) biosynthesizes a diverse array of secondary metabolites including anticancer dimeric alkaloids (vinblastine and vincristine) and antihypertensive alkaloids (ajmalicine and serpentine). The multi-step terpenoid indole alkaloids (TIAs) biosynthetic pathway in C. roseus is complex and is under strict molecular regulation. Many enzymes and genes involved in the TIAs biosynthesis have been studied in recent decades. Moreover,some regulatory proteins were found recently to control the production of TIAs in C. roseus. Based on mastering the rough scheme of the pathway and cloning the related genes, metabolic engineering of TIAs biosynthesis has been studied in C.roseus aiming at increasing the desired secondary metabolites in the past few years. The present article summarizes recent advances in isolation and characterization of TIAs biosynthesis genes and transcriptional regulators involved in the second metabolic control in C. roseus. Metabolic engineering applications in TIAs pathway via overexpression of these genes and regulators in C. roseus are also discussed.

  4. A look inside an alkaloid multisite plant: the Catharanthus logistics.

    Science.gov (United States)

    Courdavault, Vincent; Papon, Nicolas; Clastre, Marc; Giglioli-Guivarc'h, Nathalie; St-Pierre, Benoit; Burlat, Vincent

    2014-06-01

    Environmental pressures forced plants to diversify specialized metabolisms to accumulate noxious molecules such as alkaloids constituting one of the largest classes of defense metabolites. Catharanthus roseus produces monoterpene indole alkaloids via a highly elaborated biosynthetic pathway whose characterization greatly progressed with the recent expansion of transcriptomic resources. The complex architecture of this pathway, sequentially distributed in at least four cell types and further compartmentalized into several organelles, involves partially identified inter-cellular and intra-cellular translocation events acting as potential key-regulators of metabolic fluxes. The description of this spatial organization and the inherent secretion and sequestration of metabolites not only provide new insight into alkaloid cell biology and its involvement in plant defense processes but also present new biotechnological challenges for synthetic biology. PMID:24727073

  5. 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. PMID:26241493

  6. Two new C19-diterpenoid alkaloids from roots Aconitum hemsleyanium var. atropurpureum

    Institute of Scientific and Technical Information of China (English)

    Pei Tang; Dong Lin Chen; Xi Xian Jian; Feng Peng Wang

    2007-01-01

    A new franchetine-type C19-diterpenoid alkaloid 3-hydroxyfranchetine 1 and a new aconitine-type C19-diterpenoid alkaloid atropurpursine 2 have been isolated from the roots of Aconitum hemsleyanium var.atropurpureum.The structures of these new alkaloids were established on the basis of spectral data.

  7. Three new C20-diterpenoid alkaloids from Delphinium anthriscifolium var. savatieri

    Institute of Scientific and Technical Information of China (English)

    Xiao Yu Liu; Qiao Hong Chen; Feng Peng Wang

    2009-01-01

    Three new C20-diterpenoid alkaloids, designated as anthriscifolmines A-C (1-3), together with two known alkaloids denudatine and delgramine, were isolated from the whole herb of Delphinium anthriscifolium var. savatieri. The structures of these new alkaloids were elucidated on the basis of spectral data.

  8. 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)

  9. 3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens.

    Science.gov (United States)

    Liu, S C; Oguntimein, B; Hufford, C D; Clark, A M

    1990-04-01

    Further examination of the active ethanolic extract of the root bark of Cleistopholis patens by using bioassay-directed fractionation resulted in the isolation of a new alkaloid, 3-methoxysampangine (compound I), together with three known alkaloids, eupolauridine (compound II), liriodenine (compound III), and eupolauridine N-oxide (compound IV). The proposed structure of compound I was based on its physicochemical properties and spectral data. 3-Methoxysampangine exhibited significant antifungal activity against Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans. This is the first report of the isolation of liriodenine (compound III) from the root bark of C. patens. PMID:2188584

  10. Quinolizidines alkaloids: Petrosin and xestospongins from the sponge Oceanapia sp.

    Indian Academy of Sciences (India)

    Keisham Sarjit Singh; Babulal Das; Chandrakant G Naik

    2011-09-01

    A bisquinolizidine alkaloid, petrosin (1) and a series of bis-1-oxaquinolizidine, xestospongins (2-9), were obtained from the ethyl acetate extract of the sponge Oceanapia sp. Petrosin was obtained along with xestospongin- C, D, E, F, G, H, I and J having di-hetroatom 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 data. The structure of petrosin was confirmed by an X-ray diffraction study.

  11. 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 C...... and D contain endoperoxide and methylsulfonyl units, respectively. This fungus produced indole alkaloids containing an anti‐bicyclo[2.2.2]diazaoctane core, whereas A. protuberus and A. amoenus produced congeners with a syn‐bicyclo[2.2.2]diazaoctane core. Plausible biosynthetic pathways to access...

  12. Histochemical Investigation and Kinds of Alkaloids in Leaves of Different Developmental Stages in Thymus quinquecostatus

    Directory of Open Access Journals (Sweden)

    Haiting Jing

    2014-01-01

    Full Text Available Thymus quinquecostatus, with more medical value, is a kind of wild plants. In order to exploit and utilize this plant, we studied the species and locations of alkaloids in its leaves. In this paper, histochemical study of leaves at different developing stages was taken to localize the alkaloids. Meanwhile, the kinds and content of alkaloids in leaves were identified using GC-MS technique. It was found that there were two kinds of glandular trichomes, namely, peltate trichomes and capitate trichomes, on the surface of leaves, and their secretory cells could secrete alkaloids. Results showed that trichomes could secrete alkaloids as soon as the first pair of leaves formed, and there were altogether 18 kinds of alkaloids identified by GC-MS. Nearly all of these alkaloids of leaves at different developing stages were distinct from each other, except one, 3-methoxy-a-methyl-benzeneethanamine, persists at different developing stages with high concentration.

  13. Dasycarine, a New Quinoline Alkaloid from Dictamnus dasycarpus

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    Dasycarine, a new quinoline alkaloid along with five known compounds, dictamine, dihydroobacunone, obacunone, fraxinellone and b -sitosterol, were isolated from Dictamnus dasycarpus. The structure of dasycarine was identified as 4, 5, 8- trimethoxyl -3- (3- methyl -2- butenyl)- 2- quinone by 1D and 2D NMR techniques.

  14. Metabolic Engineering of Tropane Alkaloid Biosynthesis in Plants

    Institute of Scientific and Technical Information of China (English)

    Lei ZHANG; Guo-Yin KAI; Bei-Bei LU; Han-Ming ZHANG; Ke-Xuan TANG; Ji-Hong JIANG; Wan-Sheng CHEN

    2005-01-01

    Over the past decade, the evolving commercial importance of so-called plant secondary metabolites has resulted in a great interest in secondary metabolism and, particularly, in the possibilities to enhance the yield of fine metabolites by means of genetic engineering. Plant alkaloids, which constitute one of the largest groups of natural products, provide many pharmacologically active compounds. Several genes in the tropane alkaloids biosynthesis pathways have been cloned, making the metabolic engineering of these alkaloids possible. The content of the target chemical scopolamine could be significantly increased by various approaches, such as introducing genes encoding the key biosynthetic enzymes or genes encoding regulatory proteins to overcome the specific rate-limiting steps. In addition, antisense genes have been used to block competitive pathways. These investigations have opened up new, promising perspectives for increased production in plants or plant cell culture. Recent achievements have been made in the metabolic engineering of plant tropane alkaloids and some new powerful strategies are reviewed in the present paper.

  15. Revised NMR data for incartine: an alkaloid from Galanthus elwesii.

    Science.gov (United States)

    Berkov, Strahil; Reyes-Chilpa, Ricardo; Codina, Carles; Viladomat, Francesc; Bastida, Jaume

    2007-07-12

    Phytochemical studies on Galanthus elwesii resulted in the isolation of five alkaloids: incartine, hordenine, hippeastrine, 8-O-demethylhomolycorine and lycorine. The NMR data given previously for incartine were revised and completed by two-dimensional 1H-1H and 1H-13C chemical shift correlation experiments. In vitro studies on the bioactivity of incartine were carried out.

  16. Revised NMR data for Incartine: an Alkaloid from Galanthus elwesii

    Directory of Open Access Journals (Sweden)

    Jaume Bastida

    2007-07-01

    Full Text Available Phytochemical studies on Galanthus elwesii resulted in the isolation of five alkaloids: incartine, hordenine, hippeastrine, 8-O-demethylhomolycorine and lycorine. The NMR data given previously for incartine were revised and completed by two-dimensional 1H-1H and 1H-13C chemical shift correlation experiments. In vitro studies on the bioactivity of incartine were carried out.

  17. 21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 2 2010-04-01 2010-04-01 false Dietary supplements containing ephedrine alkaloids. 119.1 Section 119.1 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION DIETARY SUPPLEMENTS THAT PRESENT A SIGNIFICANT...

  18. ALKALOIDS OF THE SEDUM ACRE-GROUP (CRASSULACEAE)

    NARCIS (Netherlands)

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

    1993-01-01

    The 16 species of the Sedum acre-group were investigated for the presence of alkaloids. They are S. acre of S. ser. Acria, S. alpestre, S. annuum, S. apoleipon, S. borissovae, S. euxinum, S. grisebachii, S. laconicum, S. multiceps, S. sexangulare, S. tuberiferum, S. tuberosum, S. ursi, and S. urvill

  19. The alkaloid profiles of Sophora nuttalliana and Sophora stenophylla

    Science.gov (United States)

    Sophora is a diverse genus in the family Fabaceae, comprised of herbs, shrubs, and trees that occurs throughout the world, primarily in the northern hemisphere. Species of Sophora are known to contain quinolizidine alkaloids that are toxic and potentially teratogenic. Two perennial herbaceous spec...

  20. New Diterpenoid Alkaloids from Spiraea japonica var. ovalifolia

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    Five new diterpenoid alkaloids, 19-O-deethylspiramine N (1), deacetylspiramine S (2), spiramidine A (3), spiramidine B (4) and deacetylspiramine F (5) were isolated from the aerial parts of Spireae japonica L. f. var. ovalifolia. Their structures were charaterized mainly based on spectral analysis.

  1. In vitro cytotoxicity of various dehydropyrrolizidine ester alkaloids

    Science.gov (United States)

    Dehydropyrrolizidine alkaloids (DHPAs) are plant-derived hepato-, pneumo- and geno-toxins that are carcinogenic in several species. Because of the difficulty in isolating sufficient DHPA for toxicological studies, there are few direct comparisons of toxicity. The objectives of this study was to de...

  2. Alkaloid profiling and anticholinesterase activity of South American Lycopodiaceae species.

    Science.gov (United States)

    Konrath, Eduardo Luis; Ortega, María Gabriela; de Loreto Bordignon, Sérgio; Apel, Miriam Anders; Henriques, Amélia Teresinha; Cabrera, José Luis

    2013-02-01

    The alkaloid extracts of four Huperzia and one Lycopodiella species, from Brazilian habitats, were tested for their in vitro anticholinesterase activities. IC(50) values showed a potent acetylcholinesterase inhibition for H. reflexa (0.11 ± 0.05 μg/mL), followed by H. quadrifariata (2.0 ± 0.3 μg/mL), H. acerosa (5.5 ± 0.9 μg/mL), H. heterocarpon (25.6 ± 2.7 μg/mL) and L. cernua (42.6 ± 1.5 μg/mL). A lower inhibition of butyrylcholinesterase was observed for all species with the exception of H. heterocarpon (8.3 ± 0.9 μg/mL), whose alkaloid extract presented a selectivity for pseudocholinesterase. Moreover, the chemical study of the bioactive extracts performed by GC-MS, revealed the presence of a number of Lycopodium alkaloids belonging to the lycopodane, flabellidane and cernuane groups. Surprisingly, the potent acetylcholinesterase inhibitors huperzines A and B were not detected in the extracts, suggesting that other alkaloids may be responsible for such an effect. PMID:22117191

  3. Effect of Ergot Alkaloids on Bovine Foregut Vasculature

    Science.gov (United States)

    Ergot alkaloids induce vasoconstriction of bovine foregut vasculature. Ergovaline induced the greatest response in ruminal artery while ergovaline and ergotamine induced the greatest response in ruminal vein. Lysergic acid did not stimulate a contractile response in either the ruminal artery or vein...

  4. Scientific Opinion on Ergot alkaloids in food and feed

    NARCIS (Netherlands)

    Beuerle, T.; Benford, D.; Brimer, L.; Cottrill, B.; Doerge, D.; Dusemund, B.; Farmer, P.; Fürst, P.; Humpf, H.; Mulder, P.P.J.

    2012-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread C

  5. Scientific Opinion on Tropane alkaloids in food and feed

    NARCIS (Netherlands)

    Beuerle, T.; Benford, D.; Brimer, L.; Cottrill, B.; Doerge, D.; Dusemund, B.; Farmer, P.; Fürst, P.; Humpf, H.; Mulder, P.P.J.

    2013-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread C

  6. Tobacco NUP1 transports both tobacco alkaloids and vitamin B6.

    Science.gov (United States)

    Kato, Keita; Shitan, Nobukazu; Shoji, Tsubasa; Hashimoto, Takashi

    2015-05-01

    The purine permeases (PUPs) constitute a large plasma membrane-localized transporter family in plants that mediates the proton-coupled uptake of nucleotide bases and their derivatives, such as adenine, cytokinins, and caffeine. A Nicotiana tabacum (tobacco) PUP-family transporter, nicotine uptake permease 1 (NtNUP1), was previously shown to transport tobacco alkaloids and to affect both nicotine biosynthesis and root growth in tobacco plants. Since Arabidopsis PUP1, which belongs to the same subclade as NtNUP1, was recently reported to transport pyridoxine and its derivatives (vitamin B6), it was of interest to examine whether NtNUP1 could also transport these substrates. Direct uptake measurements in the yeast Saccharomyces cerevisiae demonstrated that NtNUP1 efficiently promoted the uptake of pyridoxamine, pyridoxine, anatabine, and nicotine. The naturally occurring (S)-isomer of nicotine was preferentially transported over the (R)-isomer. Transport studies using tobacco BY-2 cell lines overexpressing NtNUP1 or PUP1 showed that NtNUP1, similar to PUP1, transported various compounds containing a pyridine ring, but that the two transporters had distinct substrate preferences. Therefore, the previously reported effects of NtNUP1 on tobacco physiology might involve bioactive metabolites other than tobacco alkaloids. PMID:24947336

  7. 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)

  8. Warming reduces tall fescue abundance but stimulates toxic alkaloid concentrations in transition zone pastures of the U.S.

    Directory of Open Access Journals (Sweden)

    Rebecca Lynne Mcculley

    2014-10-01

    Full Text Available Tall fescue pastures cover extensive acreage in the eastern half of the United States and contribute to important ecosystem services, including the provisioning of forage for grazing livestock. Yet little is known concerning how these pastures will respond to climate change. Tall fescue’s ability to persist and provide forage under a warmer and wetter environment, as is predicted for much of this region as a result of climate change, will likely depend on a symbiotic relationship the plant can form with the fungal endophyte, Epichloë coenophiala. While this symbiosis can confer environmental stress tolerance to the plant, the endophyte also produces alkaloids toxic to insects (e.g., lolines and mammals (ergots; which can cause ‘fescue toxicosis’ in grazing animals. The negative animal health and economic consequences of fescue toxicosis make understanding the response of the tall fescue symbiosis to climate change critical for the region. We experimentally increased temperature (+3oC and growing season precipitation (+30% of the long-term mean from 2009 – 2013 in a mixed species pasture, that included a tall fescue population that was 40% endophyte-infected. Warming reduced the relative abundance of tall fescue within the plant community, and additional precipitation did not ameliorate this effect. Warming did not alter the incidence of endophyte infection within the tall fescue population; however, warming significantly increased concentrations of ergot alkaloids (by 30-40% in fall-harvested endophyte-infected individuals. Warming alone did not affect loline alkaloid concentrations, but when combined with additional precipitation, levels increased in fall-harvested material. Although future warming may reduce the dominance of tall fescue in eastern U.S. pastures and have limited effect on the incidence of endophyte infection, persisting endophyte-infected tall fescue will have higher concentrations of toxic alkaloids which may

  9. Warming reduces tall fescue abundance but stimulates toxic alkaloid concentrations in transition zone pastures of the U.S.

    Science.gov (United States)

    Mcculley, Rebecca; Bush, Lowell; Carlisle, Anna; Ji, Huihua; Nelson, Jim

    2014-10-01

    Tall fescue pastures cover extensive acreage in the eastern half of the United States and contribute to important ecosystem services, including the provisioning of forage for grazing livestock. Yet little is known concerning how these pastures will respond to climate change. Tall fescue’s ability to persist and provide forage under a warmer and wetter environment, as is predicted for much of this region as a result of climate change, will likely depend on a symbiotic relationship the plant can form with the fungal endophyte, Epichloë coenophiala. While this symbiosis can confer environmental stress tolerance to the plant, the endophyte also produces alkaloids toxic to insects (e.g., lolines) and mammals (ergots; which can cause ‘fescue toxicosis’ in grazing animals). The negative animal health and economic consequences of fescue toxicosis make understanding the response of the tall fescue symbiosis to climate change critical for the region. We experimentally increased temperature (+3oC) and growing season precipitation (+30% of the long-term mean) from 2009 - 2013 in a mixed species pasture, that included a tall fescue population that was 40% endophyte-infected. Warming reduced the relative abundance of tall fescue within the plant community, and additional precipitation did not ameliorate this effect. Warming did not alter the incidence of endophyte infection within the tall fescue population; however, warming significantly increased concentrations of ergot alkaloids (by 30-40%) in fall-harvested endophyte-infected individuals. Warming alone did not affect loline alkaloid concentrations, but when combined with additional precipitation, levels increased in fall-harvested material. Although future warming may reduce the dominance of tall fescue in eastern U.S. pastures and have limited effect on the incidence of endophyte infection, persisting endophyte-infected tall fescue will have higher concentrations of toxic alkaloids which may exacerbate fescue

  10. Biodegradable poly(lactic acid) microspheres containing total alkaloids of Caulis sinomenii

    Indian Academy of Sciences (India)

    Wen Zhang; Xiaojie Lin; Xingxiang Zhang

    2011-12-01

    The fabrication of biodegradable poly(lactic acid) (PLA) microspheres containing total alkaloids of Caulis sinomenii was investigated. The formation, diameter, morphology and properties of the microspheres were characterized using Fourier transform infrared spectroscopy (FT–IR), laser particle size analyser and scanning electron microscopy (SEM), etc. In vitro releasing behaviour was also investigated using UV-Vis spectrometer. As a result, the drug-loaded microspheres with a narrower distributive, rounder and smoother surface were prepared. Drug-releasing behaviour from microspheres was affected by the concentration of emulsifier and the stirring rate. The results demonstrated that a medicated system, which can be potentially applied within a drug delivery system, was designed. This system acts in a systematic manner for the treatment of rheumatoid arthritis.

  11. 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.

  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. A submarine journey: the pyrrole-imidazole alkaloids.

    Science.gov (United States)

    Forte, Barbara; Malgesini, Beatrice; Piutti, Claudia; Quartieri, Francesca; Scolaro, Alessandra; Papeo, Gianluca

    2009-11-27

    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.

  14. A Submarine Journey: The Pyrrole-Imidazole Alkaloids

    Science.gov (United States)

    Forte, Barbara; Malgesini, Beatrice; Piutti, Claudia; Quartieri, Francesca; Scolaro, Alessandra; Papeo, Gianluca

    2009-01-01

    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. PMID:20098608

  15. Potent Antiplasmodial Alkaloids and Flavonoids from Dasymaschalon acuminatum

    Directory of Open Access Journals (Sweden)

    Ratchanaporn Chokchaisiri

    2015-01-01

    Full Text Available A new aporphine alkaloid, 7-epi-duguetine (1 together with one known alkaloid, dicentrinone (2, and four known flavonoids, quercetin 3,7-dimethyl ether 3′ -O- α -L-rhamnopyranosyl-(1 g 2-β-D-glucopyranoside (3, galangin 5-methyl ether (4, 5,7-dimethoxy-3-hydroxyflavone (5, and 3,5,7-trimethoxyflavone (6, were isolated from the leaves of Dasymaschalon acuminatum , a new plant species which has not been investigated phytochemically before. The structures of the isolated compounds were elucidated through extensive NMR spectroscopic analysis. All isolates were evaluated for antiplasmodial activity against Plasmodium falciparum strain K1 and 7- epi -duguetine was found to exhibit potent activity with an IC 50 of 0.385 m g/ml .

  16. Anti-leishmanial activity of alkaloidal extract from Aspidosperma ramiflorum

    Directory of Open Access Journals (Sweden)

    Izabel Cristina Piloto Ferreira

    2004-05-01

    Full Text Available Infections due to protozoa of the genus Leishmania are a major worldwide health problem, with high endemicity in developing countries. The drugs of choice for the treatment of leishmaniasis are the pentavalent antimonials (SbV, which present renal and cardiac toxicity. Besides, the precise chemical structure and mechanism of action of these drugs are unknown up to date. In order to find new drugs against leishmaniasis, we have been studying extracts of Brazilian trees. In the present study, we have evaluated the effectiveness of an alkaloid extract of Aspidosperma ramiflorum Muell. Arg. (Apocynaceae, against the extracellular forms promastigotes of L. (L. amazonensis and L. (V. braziliensis. The alkaloid extract of A. ramiflorum was much more effective against L. (L. amazonensis (LD50 < 47 µg/ml than L. (V. braziliensis. Based on these in vitro results against L. (L. amazonensis new studies should be made to find the compounds with anti-leishmanial activity.

  17. Antiplasmodial activities of furoquinoline alkaloids from Teclea afzelii.

    Science.gov (United States)

    Wansi, Jean Duplex; Hussain, Hidayat; Tcho, Alain Tadjong; Kouam, Simeon F; Specht, Sabine; Sarite, Salem Ramadan; Hoerauf, Achim; Krohn, Karsten

    2010-05-01

    The study of the chemical constituents of the stem bark of Teclea afzelii (Rutaceae) has resulted in the isolation and characterization of four furoquinoline alkaloids, namely kokusaginine (1), tecleaverdoornine (2), maculine (3) and montrifoline (4) together with lupeol (5) and beta-sitosterol glucopyranoside (6). The structures of the isolated compounds were elucidated based on spectroscopic studies. The antimalarial activity of compounds 1-4 against Plasmodium falciparum in vitro shows partial suppression of parasitic growth. PMID:19496062

  18. Alkaloid and other chemical constituents from Psychotria stachyoides Benth

    Energy Technology Data Exchange (ETDEWEB)

    Pimenta, Antonia T.A.; Uchoa, Daniel E.A.; Silveira, Edilberto R.; Lima, Mary Anne S. [Departamento de Quimica Organica e Inorganica, Universidade Federal do Ceara, Fortaleza, CE (Brazil); Braz-Filho, Raimundo, E-mail: mary@dqoi.ufc.br [Centro de Ciencias, Universidade Estadual do Norte Fluminense and Universidade Federal Rural do Rio de Janeiro, Campos dos Goytacazes-RJ (Brazil)

    2011-09-15

    The organic extracts of leaves and roots of Psychotria stachyoides provided the new glucoside monoterpenoid indole alkaloid N-demethylcorreantoside, besides bizantionoside B, a-amyrin, alizarine methyl-ether, rubiadine, scopoletin, barbinevic acid and a mixture of b-sitosterol and stigmasterol glucosides. The structural characterization of the isolates was established based on infrared spectroscopy (IR), mass spectrometry (MS) and, particularly, 1D and 2D nuclear magnetic resonance (NMR). (author)

  19. 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)

  20. 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...... and infections, this will exemplify how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways...

  1. Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives

    OpenAIRE

    Gaziano, Roberta; Moroni, Gabriella; Buè, Cristina; Miele, Martino Tony; Sinibaldi-Vallebona, Paola; Pica, Francesca

    2016-01-01

    Historically, natural products have represented a significant source of anticancer agents, with plant-derived drugs becoming increasingly explored. In particular, sanguinarine is a benzophenanthridine alkaloid obtained from the root of Sanguinaria canadensis, and from other poppy Fumaria species, with recognized anti-microbial, anti-oxidant and anti-inflammatory properties. Recently, increasing evidence that sanguinarine exibits anticancer potential through its capability of inducing apoptosi...

  2. Alkaloids of in vitro cultures of Rhazya stricta

    OpenAIRE

    Akhgari, Amir

    2015-01-01

    Rhazya stricta Decne. (Apocynaceae) is a traditional medicinal plant in the Middle East and South Asia. It produces a large number of terpenoid indole alkaloids(TIAs), some of which possess important pharmacological properties. This study focused on the establishment of biotechnological production tools of R. stricta, namely undifferentiated cell cultures, and an Agrobacterium rhizogenes-mediated transformation method to obtain hairy roots expressing heterologous genes from the early TIA path...

  3. Antimalarial diterpene alkaloids from the seeds of Caesalpinia minax.

    Science.gov (United States)

    Ma, Guoxu; Sun, Zhaocui; Sun, Zhonghao; Yuan, Jingquan; Wei, Hua; Yang, Junshan; Wu, Haifeng; Xu, Xudong

    2014-06-01

    Two new diterpene alkaloids, caesalminines A (1) and B (2), possessing a tetracyclic cassane-type furanoditerpenoid skeleton with γ-lactam ring, were isolated from the seeds of Caesalpinia minax. Their structures were determined by different spectroscopic methods and ECD calculation. The plausible biosynthetic pathway of caesalminines A and B was proposed. The anti-malarial activity of compounds 1 and 2 is presented with IC50 values of 0.42 and 0.79 μM, respectively.

  4. Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus

    OpenAIRE

    Jianhua Zhu; Mingxuan Wang; Wei Wen; Rongmin Yu

    2015-01-01

    Catharanthus roseus produces a wide range of terpenoid indole alkaloids (TIA). Many of them, such as vinblastine and vincristine, have significant bioactivity. They are valuable chemotherapy drugs used in combination with other drugs to treat lymphoma and leukemia. The TIA biosynthetic pathway has been investigated for many years, for scientific interest and for their potential in manufacturing applications, to fulfill the market demand. In this review, the progress and perspective of C. rose...

  5. Enantioselective Nazarov Cyclization Catalyzed by a Cinchona Alkaloid Derivative

    Science.gov (United States)

    Huang, Yu-Wen; Frontier, Alison J.

    2015-01-01

    Nucleophilic catalysts for a 1,6 addition/Nazarov cyclization/elimination sequence were evaluated for their ability to induce enantioselectivity in the electrocyclization step. Of the tertiary amines examined, it was found that a cinchona alkaloid derivative was able to generate substituted 5-hydroxy γ-methylene cyclopentenones with excellent enantioselectivity. The study results suggest that successful cyclization depends upon the ability of the dienyl diketone substrate to readily adopt an s-cis conformation. PMID:26085696

  6. Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

    OpenAIRE

    Larsson, Sonny; Rønsted, Nina

    2014-01-01

    The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. 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. Fol...

  7. Short-term toxicity studies of loline alkaloids in mice.

    Science.gov (United States)

    Finch, S C; Munday, J S; Munday, R; Kerby, J W F

    2016-08-01

    Epichloë endophytes have been used successfully in pastoral systems to reduce the impact of insect pests through the expression of secondary metabolites. The use of endophytes could be extended to other plant species, such as cereal crops, where the production of bioactive secondary metabolites would reduce the reliance on pesticides for insect control. The success of this approach is dependent on the selection of an appropriate secondary metabolite target which must not only be effective against insect pests but also be safe for grazing and monogastric animals. The loline alkaloids have been identified as possible target metabolites as they are associated with potent effects on insects and low toxicity to grazing animals. The purpose of the current study was to generate toxicological data on the loline alkaloids in a monogastric system using mice. Male and female mice were fed 415 mg/kg/day total lolines for a 3-week period. The loline treatment caused no statistically significant effect on gross pathology, histology, haematology, blood chemistry, heart rate, blood pressure or motor coordination. Reduced weight gain and food consumption were noted in the loline groups during the initial stages of the experiment. This experiment raises no food safety concerns for the loline alkaloids. PMID:27276360

  8. Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus.

    Science.gov (United States)

    Pardanani, J H; McLaughlin, J L; Kondrat, R W; Cooks, R G

    1977-01-01

    Agurell has previously detected (tlc, glc-ms) tyramine, 3-methoxytyramine, and two unknown alkaloids in the Peruvian cactus, Trichocereus peruvianus Br. and R. The presence of mescaline in other similar Trichocereus species prompted us to reinvestigate this species, which is commercially available in the United States. The nonphenolic alkaloid extracts yielded an abundance of crystalline mescaline hydrochloride (0.82% yield) and a trace of 3,4-dimethoxyphenethylamine (tlc-ms). Crystalline tyramine hydrochloride, 3-methoxytyramine hydrochloride, and 3,5 dimethoxy-4-hydroxphenethylamine hydrochloride were isolated from the phenolic alkaloid extracts; the last compound has not been previously crystallized from nature, although it is the immediate biosynthetic precursor of mescaline. Crystalline 2-chloromescaline hydrochloride was isolated drom the nonphenolic extracts; but, as determined by mass-analyzed ion kinetic energy spectrometry, this new compound is an extraction artifact. Both 2-chloromescaline and 2.6-dichloromescaline hydrochlorides were prepared synthetically from mescaline. This cactus species has a mescaline content equal or superior to peyote and should be legally controlled as an item of drug abuse.

  9. Metabolic engineering for the production of plant isoquinoline alkaloids.

    Science.gov (United States)

    Diamond, Andrew; Desgagné-Penix, Isabel

    2016-06-01

    Several plant isoquinoline alkaloids (PIAs) possess powerful pharmaceutical and biotechnological properties. Thus, PIA metabolism and its fascinating molecules, including morphine, colchicine and galanthamine, have attracted the attention of both the industry and researchers involved in plant science, biochemistry, chemical bioengineering and medicine. Currently, access and availability of high-value PIAs [commercialized (e.g. galanthamine) or not (e.g. narciclasine)] is limited by low concentration in nature, lack of cultivation or geographic access, seasonal production and risk of overharvesting wild plant species. Nevertheless, most commercial PIAs are still extracted from plant sources. Efforts to improve the production of PIA have largely been impaired by the lack of knowledge on PIA metabolism. With the development and integration of next-generation sequencing technologies, high-throughput proteomics and metabolomics analyses and bioinformatics, systems biology was used to unravel metabolic pathways allowing the use of metabolic engineering and synthetic biology approaches to increase production of valuable PIAs. Metabolic engineering provides opportunity to overcome issues related to restricted availability, diversification and productivity of plant alkaloids. Engineered plant, plant cells and microbial cell cultures can act as biofactories by offering their metabolic machinery for the purpose of optimizing the conditions and increasing the productivity of a specific alkaloid. In this article, is presented an update on the production of PIA in engineered plant, plant cell cultures and heterologous micro-organisms. PMID:26503307

  10. 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.

  11. Penentuan Sifat Kimia Fisika Senyawa Alkaloid Hasil Isolasi Dari Daun Bandotan (Ageratum Conyzoides Linn.)

    OpenAIRE

    Hasibuan, Poppy Anjelisa Z.; Nainggolan, Marline

    2010-01-01

    Extraction, isolation and identification of alkaloid from bandotan’s leaf (Ageratum conyzoides Linn.) has been carried out. Extraction was done by maceration method by using methanol. Isolation has been carried out by adding acid base to give crude alkaloid. The isolation followed by column chromatography by using chloroform-methanol-amonia as mobile phase (85-15-1) and silica gel 60 (mesh 70-230 ASTM) as statis phase. The result of column chromatography has get one white crystal alkaloid...

  12. Radiation Processed Carrageenan Improves Plant Growth, Physiological Activities, and Alkaloids Production in Catharanthus roseus L.

    OpenAIRE

    Naeem, M.; Mohd Idrees; Tariq Aftab; M. Masidur Alam; Khan, M. Masroor A.; Moin Uddin; Lalit Varshney

    2015-01-01

    Catharanthus roseus (L.) G. Don (Apocynaceae) is a medicinal plant that produces indole alkaloids used in cancer chemotherapy. Commercially important antineoplastic alkaloids, namely, vinblastine and vincristine, are mainly present in the leaves of C. roseus. Gamma-rays irradiated carrageenan (ICR) has been proven as plant growth promoting substance for a number of medicinal and agricultural plants. Considering the importance of ICR as a promoter of plant growth and alkaloids production in C....

  13. MEXICAN WILD LUPINES AS A SOURCE OF QUINOLIZIDINE ALKALOIDS OF ECONOMIC POTENTIAL

    OpenAIRE

    M.A. Ruiz-López; P.M. García-López; R. Rodríguez-Macías; J.F. Zamora Natera; M.L. Isaac-Virgen; M. Múzquiz

    2010-01-01

    Quinolizidine alkaloids such as lupanine, 13-hydroxylupanine, multifl orine, angustifoline and sparteine, which are present in the species of the genus Lupinus, have been reported to have biopesticide and pharmacological activities. The aim of this study was to quantify the content and variation of the individual alkaloids in seeds of L. mexicanus, L. exaltatus, L. montanus and L. stipulatus collected in different states of Mexico. Lupanine was the major (5.05 ± 0.37 mg/g) alkaloid found in L...

  14. Radiolytically degraded sodium alginate enhances plant growth, physiological activities and alkaloids production in Catharanthus roseus L.

    OpenAIRE

    Naeem, M.; Tariq Aftab; Abid A. Ansari; Mohd Idrees; Akbar Ali; Khan, M. Masroor A.; Moin Uddin; Lalit Varshney

    2015-01-01

    Catharanthus roseus (L.) G. Don (Family Apocynaceae) is a medicinal plant that produces indole alkaloids used in cancer chemotherapy. The anticancerous alkaloids, viz. vinblastine and vincristine, are mainly present in the leaves of C. roseus. High demand and low yield of these alkaloids in the plant has led to explore the alternative means for their production. Gamma irradiated sodium alginate (ISA) has proved as a plant growth promoting substance for various medicinal and agricultural crops...

  15. Binary stress induces an increase in indole alkaloid biosynthesis in Catharanthus roseus

    OpenAIRE

    Wei ZHU; Yang, Bingxian; Komatsu, Setsuko; Lu, Xiaoping; Li, Ximin; Tian, Jingkui

    2015-01-01

    Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abund...

  16. Binary Stress Induces an Increase in Indole Alkaloid Biosynthesis in Catharanthus roseus

    OpenAIRE

    Wei eZhu; Bingxian eYang; Setsuko eKomatsu; Xiaoping eLu; Ximin eLi; Jingkui eTian

    2015-01-01

    Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abund...

  17. A virus-induced gene silencing approach to understanding alkaloid metabolism in Catharanthus roseus

    OpenAIRE

    Liscombe, David K.; O’Connor, Sarah E.

    2011-01-01

    The anticancer agents vinblastine and vincristine are bisindole alkaloids derived from coupling vindoline and catharanthine, monoterpenoid indole alkaloids produced exclusively by Madagascar periwinkle (Catharanthus roseus) plants. Industrial production of vinblastine and vincristine currently relies on isolation from C. roseus leaves, a process that affords these compounds in 0.0003–0.01% yields. Metabolic engineering efforts to improve alkaloid content or provide alternative sources of the ...

  18. Alkaloids Induce Programmed Cell Death in Bloodstream Forms of Trypanosomes (Trypanosoma b. brucei)

    OpenAIRE

    Michael Wink; Vera Rosenkranz

    2008-01-01

    The potential induction of a programmed cell death (PCD) in Trypanosoma b. brucei by 55 alkaloids of the quinoline, quinolizidine, isoquinoline, indole, terpene, tropane, steroid, and piperidine type was studied by measuring DNA fragmentation and changes in mitochondrial membrane potential. For comparison, the induction of apoptosis by the same alkaloids in human leukemia cells (Jurkat APO-S) was tested. Several alkaloids of the isoquinoline, quinoline, indole and steroidal type (berberine, c...

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

    OpenAIRE

    Chi Zhang; Yuanming Zhang; Hua Shao; Xiaoli Huang

    2013-01-01

    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. harma...

  20. Elemental step thermodynamics of various analogues of indazolium alkaloids to obtaining hydride in acetonitrile.

    Science.gov (United States)

    Lei, Nan-Ping; Fu, Yan-Hua; Zhu, Xiao-Qing

    2015-12-21

    A series of analogues of indazolium alkaloids were designed and synthesized. The thermodynamic driving forces of the 6 elemental steps for the analogues of indazolium alkaloids to obtain hydride in acetonitrile were determined using an isothermal titration calorimeter (ITC) and electrochemical methods, respectively. The effects of molecular structure and substituents on the thermodynamic driving forces of the 6 steps were examined. Meanwhile, the oxidation mechanism of NADH coenzyme by indazolium alkaloids was examined using the chemical mimic method. The result shows that the oxidation of NADH coenzyme by indazolium alkaloids in vivo takes place by one-step concerted hydride transfer mechanism.

  1. Integration of Transcriptome and Proteome Reveals the Alkaloids Biosynthesis in Macleaya cordata and Macleaya microcarpa

    Institute of Scientific and Technical Information of China (English)

    Yisong Liu; Wei Liu; Xiubing Liu; Peng Huang; Pengcheng Zhu; Pi Cheng; Jing Zeng

    2012-01-01

    The Macleaya spp.,including Macleaya cordata and Macleaya microcarpa,are traditional anti-virus,inflammation eliminating,and insecticide herb medicines for their isoquinoline alkaloids.The studies of their alkaloids biosyntheses are urgent for better application.To further characterize their alkaloids biosyntheses,we elaborately designed the transcriptome,proteome and metabolism profiling for 10 samples of both species to explore their alkaloids biosyntheses.From the transcriptome data,we obtained 69367 and 78255 unigenes for M.cordata and M.microcarpa,which two thirds of them were similar to sequences in public databases.By metabolism profiling,we observed reverse patterns in different organs of two species for alkaloids sanguinarine,chelerythrine,protopine,and allocryptopine.Thus,the expression of enzymes in alkaloid biosynthesis pathways and the differential gene expression for multiple interesting comparisons were analyzed.We identified more than 1000 proteins and hundreds of differentially expressed proteins from iTRAQ proteome data.Furthermore,the ultrastructure of laticifers by SEM proved the alkaloids accumulation in the mature roots.This study suggests strongly that root maybe the organ for major alkaloids biosynthesis.Except for biosynthesis,the alkaloids storage and transport were also important for their accumulation.This work provided the first genome scale analysis for Macleaya spp.and shed light on researches for non-model plants by integrating different high-throughput technologies.

  2. Dehydropyrrolizidine alkaloids in two Cryptantha species: Including two new open chain diesters one of which is amphoteric

    Science.gov (United States)

    A livestock poisoning outbreak near Kingman, Arizona, USA, potentially linked to dehydropyrrolizidine alkaloids, prompted an evaluation of some local plants for the presence of these hepatotoxic alkaloids. Two species of Cryptantha, a Boraginaceous genus previously shown to produce potentially toxic...

  3. Aporphine alkaloid contents increase with moderate nitrogen supply in Annona diversifolia Saff. (Annonaceae) seedlings during diurnal periods.

    Science.gov (United States)

    Orozco-Castillo, José Agustín; Cruz-Ortega, Rocío; Martinez-Vázquez, Mariano; González-Esquinca, Alma Rosa

    2016-10-01

    Aporphine alkaloids are secondary metabolites that are obtained in low levels from species of the Annonaceae family. Nitrogen addition may increase the alkaloid content in plants. However, previous studies published did not consider that nitrogen could change the alkaloid content throughout the day. We conducted this short-term study to determine the effects of nitrogen applied throughout the diurnal period on the aporphine alkaloids via measurements conducted on the roots, stems and leaves of Annona diversifolia seedlings. The 60-day-old seedlings were cultured with the addition of three levels of nitrogen (0, 30 and 60 mM), and alkaloid extracts were analysed using high-performance liquid chromatography. The highest total alkaloid content was measured in the treatment with moderate nitrogen supply. Further, the levels of aporphine alkaloids changed significantly in the first few hours of the diurnal period. We conclude that aporphine alkaloid content increased with moderate nitrogen supply and exhibited diurnal variation.

  4. Atropurpuran – Missing Biosynthetic Link Leading to the Hetidine and Arcutine C20-Diterpenoid Alkaloids or an Oxidative Degradation Product?

    Science.gov (United States)

    Weber, Manuel; Owens, Kyle; Sarpong, Richmond

    2015-01-01

    A possible biosynthetic link between atropurpuran, the hetidine diterpenoid alkaloids and the alkaloid arcutine and congeners is proposed. The feasibility of aspects of this biosynthesis, especially key 1,2-rearrangements, have been examined computationally. PMID:26028789

  5. CrBPF1 overexpression alters transcript levels of terpenoid indole alkaloid biosynthetic and regulatory genes.

    Science.gov (United States)

    Li, Chun Yao; Leopold, Alex L; Sander, Guy W; Shanks, Jacqueline V; Zhao, Le; Gibson, Susan I

    2015-01-01

    Terpenoid indole alkaloid (TIA) biosynthesis in Catharanthus roseus is a complex and highly regulated process. Understanding the biochemistry and regulation of the TIA pathway is of particular interest as it may allow the engineering of plants to accumulate higher levels of pharmaceutically important alkaloids. Toward this end, we generated a transgenic C. roseus hairy root line that overexpresses the CrBPF1 transcriptional activator under the control of a β-estradiol inducible promoter. CrBPF1 is a MYB-like protein that was previously postulated to help regulate the expression of the TIA biosynthetic gene STR. However, the role of CrBPF1 in regulation of the TIA and related pathways had not been previously characterized. In this study, transcriptional profiling revealed that overexpression of CrBPF1 results in increased transcript levels for genes from both the indole and terpenoid biosynthetic pathways that provide precursors for TIA biosynthesis, as well as for genes in the TIA biosynthetic pathway. In addition, overexpression of CrBPF1 causes increases in the transcript levels for 11 out of 13 genes postulated to act as transcriptional regulators of genes from the TIA and TIA feeder pathways. Interestingly, overexpression of CrBPF1 causes increased transcript levels for both TIA transcriptional activators and repressors. Despite the fact that CrBPF1 overexpression affects transcript levels of a large percentage of TIA biosynthetic and regulatory genes, CrBPF1 overexpression has only very modest effects on the levels of the TIA metabolites analyzed. This finding may be due, at least in part, to the up-regulation of both transcriptional activators and repressors in response to CrBPF1 overexpression, suggesting that CrBPF1 may serve as a "fine-tune" regulator for TIA biosynthesis, acting to help regulate the timing and amplitude of TIA gene expression. PMID:26483828

  6. CrBPF1 overexpression alters transcript levels of terpenoid indole alkaloid biosynthetic and regulatory genes

    Directory of Open Access Journals (Sweden)

    Chun Yao eLi

    2015-10-01

    Full Text Available Terpenoid indole alkaloid (TIA biosynthesis in Catharanthus roseus is a complex and highly regulated process. Understanding the biochemistry and regulation of the TIA pathway is of particular interest as it may allow the engineering of plants to accumulate higher levels of pharmaceutically important alkaloids. Towards this end, we generated a transgenic C. roseus hairy root line that overexpresses the CrBPF1 transcriptional activator under the control of a β-estradiol inducible promoter. CrBPF1 is a MYB-like protein that was previously postulated to help regulate the expression of the TIA biosynthetic gene STR. However, the role of CrBPF1 in regulation of the TIA and related pathways had not been previously characterized. In this study, transcriptional profiling revealed that overexpression of CrBPF1 results in increased transcript levels for genes from both the indole and terpenoid biosynthetic pathways that provide precursors for TIA biosynthesis, as well as for genes in the TIA biosynthetic pathway. In addition, overexpression of CrBPF1 causes increases in the transcript levels for 11 out of 13 genes postulated to act as transcriptional regulators of genes from the TIA and TIA feeder pathways. Interestingly, overexpression of CrBPF1 causes increased transcript levels for both TIA transcriptional activators and repressors. Despite the fact that CrBPF1 overexpression affects transcript levels of a large percentage of TIA biosynthetic and regulatory genes, CrBPF1 overexpression has only very modest effects on the levels of the TIA metabolites analyzed. This finding may be due, at least in part, to the up-regulation of both transcriptional activators and repressors in response to CrBPF1 overexpression, suggesting that CrBPF1 may serve as a fine-tune regulator for TIA biosynthesis, acting to help regulate the timing and amplitude of TIA gene expression.

  7. 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. PMID:17230349

  8. 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...

  9. The toxicity of Poison Dart Frog alkaloids against the Fire Ant (Solenopsis invicta)

    Science.gov (United States)

    Hundreds of alkaloids, representing over 20 structural classes, have been identified from the skin of neotropical poison frogs (Dendrobatidae). These alkaloids are derived from arthropod prey of the frogs, and are generally are believed to deter vertebrate predators. We developed a method to put ind...

  10. Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii D.C.

    Science.gov (United States)

    Paulo, M de Q; Barbosa-Filho, J M; Lima, E O; Maia, R F; Barbosa, R de C; Kaplan, M A

    1992-02-01

    Bark of Annona salzmanii D.C. (Annonaceae), used in Brazilian folk medicine, was found to contain four benzylisoquinoline alkaloids, namely reticuline, anonaine, laurelliptine and isoboldine. Only anonaine possesses some antibacterial property while all four alkaloids show some antifungal activity. PMID:1501491

  11. A convenient microwave-assisted synthesis of cinchona alkaloid-derived ligands

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    An efficient synthesis of cinchona alkaloid-derived ligands based on solvent-free microwave-assisted reaction was described. The coupling of 1,4-dichlorophthalazine or 3,6-dichloropyridazine with quinine, cinchonine or cinchonidine provide bis- or mono-cinchona alkaloid-derived ligands in moderate to good yields (52-89%) within 15 rain under optimum microwave conditions.

  12. CHINESE BITTERSWEET ALKALOID Ⅲ,A NEW COMPOUND FROM CELASTR US ANGULATUS

    Institute of Scientific and Technical Information of China (English)

    WEI-PING YIN; TIAN-ZENG ZHAO; JING-GUO FU

    2001-01-01

    A novel skeleton alkaloid named Chinese Bittersweet Alkaloid Ⅲ from the leaves of C. angulatus was reported. The structure and its stereochemistry were established by IR, 1Dand 2DNMR (1H-1HCOSY, HMQC, HMBC, NOESY), MS and elemental analysis.

  13. Heterozygous P53 knockout mouse model for dehydropyrrolizidine alkaloid-induced carcinogenesis

    Science.gov (United States)

    Dehydropyrrolizidine alkaloids are a large, structurally diverse group of plant-derived protoxins that are potentially carcinogenic. With worldwide significance, these alkaloids can contaminate or be naturally present in the human food supply. To develop a small animal model that may be used to com...

  14. Isolation of a minor nitro-alkaloid from the aerial parts of Duguetia furfuracea--Annonaceae.

    Science.gov (United States)

    Carollo, Carlos Alexandre; de Siqueira, Joao Maximo

    2009-01-01

    The refractionation of an alkaloidal extract of the leaves and twigs of Duguetia furfuracea has provided a minor aporphinoid alkaloid, named (+)-8-nitrous-isocorydine or (+)-1,2,3-trymethoxy-11-hydroxy-8-nitrous- aporphine. The structure of the new compound was elucidated by spectroscopic methods, notably 2D NMR and HRESIMS.

  15. New C19-Diterpenoid Alkaloids from the Roots of Delphinium Giraldii

    Institute of Scientific and Technical Information of China (English)

    周先礼; 陈巧鸿; 陈东林; 王锋鹏

    2003-01-01

    Three new C19-diterpenoid alkaloids, giraldines A (1), B (3) and C (4), were isolated from the roots of Delphinium giraldii Diels, together with three known C19-diterpenoid alkaloids, dihydrogadesine (5), tatsiensine (6) and siwanine A (7), as well as their structures were elucidated by chemical evidence and spectral analyses, including IR, MS, 1D NMR and 2D NMR.

  16. 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.

  17. The Eco-physiological Function of Alkaloid and Factors Influencing the Alkaloid Formation%生物碱的生理生态功能及影响其形成的因素

    Institute of Scientific and Technical Information of China (English)

    张阳; 刘海涛; 张昭; 马春放; 张志鹏; 陈瑶; 张本刚

    2014-01-01

    Production of plant secondary metabolite is the result of long-term interaction between plants and environment, and the alkaloid plays an important role in the process of growth and development of plants as one of the secondary metabolites with higher medicinal value. This paper summarizes the eco-physiological function of alkaloid in terms of regulating of plant growth, responding to environmental stress and defending plant diseases and insect pests, as well as the ecological factors and genetic factors that affecting the formation of alkaloids in plants, and further discusses the interaction between plants and environment. It may provide new approaches for completely and deeply comprehending correlations between plants and environment, and producing high quality traditional Chinese medicine.%植物次生代谢产物是植物与环境之间长期相互作用的结果,生物碱作为药用价值极高的一类次生代谢产物,在植物的生长发育过程中扮演着重要角色。概述了生物碱在调节植物生长、应对环境胁迫、防御病虫害等方面的主要生理生态功能;同时总结了影响植物中生物碱形成的生态因素和遗传因素;并深入探讨了生物碱与环境的内在联系。为进一步认识生物碱与生物和非生物环境的相互关系,生产高产优质中药材提供思路。

  18. Tall fescue seed extraction and partial purification of ergot alkaloids

    Directory of Open Access Journals (Sweden)

    Lowell eBush

    2014-12-01

    Full Text Available Many substances in the tall fescue/endophyte association (Schedonorus arundinaceus/Epichloë coenophiala have biological activity. Of these compounds only the ergot alkaloids are known to have significant mammalian toxicity and the predominant ergot alkaloids are ergovaline and ergovalinine. Because synthetically produced ergovaline is difficult to obtain, we developed a seed extraction and partial purification protocol for ergovaline/ergovalinine that provided a biologically active product. Tall fescue seed was ground and packed into several different sized columns for liquid extraction. Smaller particle size and increased extraction time increased efficiency of extraction. Our largest column was a 114 × 52 × 61 cm (W×L×D stainless steel tub. Approximately 150 kg of seed could be extracted in this tub. The extraction was done with 80% ethanol. When the solvent front migrated to bottom of the column, flow was stopped and seed was allowed to steep for at least 48 h. Light was excluded from the solvent from the beginning of this step to the end of the purification process. Following elution, ethanol was removed from the eluate by evaporation at room temperature. Resulting syrup was freeze-dried. About 80% recovery of alkaloids was achieved with 18-fold increase in concentration of ergovaline. Initial purification of the dried product was accomplished by extracting with hexane/water (6:1, v/v and the hexane fraction was discarded. The aqueous fraction was extracted with chloroform, the aqueous layer discarded, after which the chloroform was removed with a resulting 20-fold increase of ergovaline. About 65% of the ergovaline was recovered from the chloroform residue for an overall recovery of 50%. The resultant partially purified ergovaline had biological activities in in vivo and in vitro bovine bioassays that approximate that of synthetic ergovaline.

  19. Bromopyrrole Alkaloids as Lead Compounds against Protozoan Parasites

    Directory of Open Access Journals (Sweden)

    Deniz Tasdemir

    2010-07-01

    Full Text Available In the present study,13 bromopyrrole alkaloids, including the oroidin analogs hymenidin (2, dispacamide B (3 and dispacamide D (4, stevensine (5 and spongiacidin B (6, their derivatives lacking the imidazole ring bromoaldisin (7, longamide B (8 and longamide A (9, the dimeric oroidin derivatives sceptrin (10 and dibromopalau’amine (11, and the non-oroidin bromopyrrolohomoarginin (12, manzacidin A (13, and agelongine (14, obtained from marine sponges belonging to Axinella and Agelas generahave been screened in vitro against four parasitic protozoa, i.e., two Trypanosoma species (T. brucei rhodesiense and T. cruzi, Leishmania donovani and Plasmodium falciparum (K1 strain, a chloroquine resistant strain, responsible of human diseases with high morbidity and, in the case of malaria, high mortality. Our results indicate longamide B (8 and dibromopalau’amine (11 to be promising trypanocidal and antileishmanial agents, while dispacamide B (3 and spongiacidin B (6 emerge as antimalarial lead compounds.In addition,evaluation of the activity of the test alkaloids (2–14 against three different enzymes (PfFabI, PfFabG, PfFabZ involved in the de novo fatty acid biosynthesis pathway of P. falciparum (PfFAS-II identified bromopyrrolohomoarginin (12 as a potent inhibitor of PfFabZ. The structural similarity within the series of tested molecules allowed us to draw some preliminary structure-activity relationships. Tests against the mammalian L6 cells revealed important clues on therapeutic index of the metabolites. This is the first detailed study on the antiprotozoal potential of marine bromopyrrole alkaloids.

  20. Overexpression of ORCA3 and G10H in Catharanthus roseus Plants Regulated Alkaloid Biosynthesis and Metabolism Revealed by NMR-Metabolomics

    Science.gov (United States)

    Pan, Qifang; Wang, Quan; Yuan, Fang; Xing, Shihai; Zhao, Jingya; Choi, Young Hae; Verpoorte, Robert; Tian, Yuesheng; Wang, Guofeng; Tang, Kexuan

    2012-01-01

    In order to improve the production of the anticancer dimeric indole alkaloids in Catharanthuse roseus, much research has been dedicated to culturing cell lines, hairy roots, and efforts to elucidate the regulation of the monoterpenoid indole alkaloid (MIA) biosynthesis. In this study, the ORCA3 (Octadecanoid-derivative Responsive Catharanthus AP2-domain) gene alone or integrated with the G10H (geraniol 10-hydroxylase) gene were first introduced into C. roseus plants. Transgenic C. roseus plants overexpressing ORCA3 alone (OR lines), or co-overexpressing G10H and ORCA3 (GO lines) were obtained by genetic modification. ORCA3 overexpression induced an increase of AS, TDC, STR and D4H transcripts but did not affect CRMYC2 and G10H transcription. G10H transcripts showed a significant increase under G10H and ORCA3 co-overexpression. ORCA3 and G10H overexpression significantly increased the accumulation of strictosidine, vindoline, catharanthine and ajmalicine but had limited effects on anhydrovinblastine and vinblastine levels. NMR-based metabolomics confirmed the higher accumulation of monomeric indole alkaloids in OR and GO lines. Multivariate data analysis of 1H NMR spectra showed change of amino acid, organic acid, sugar and phenylpropanoid levels in both OR and GO lines compared to the controls. The result indicated that enhancement of MIA biosynthesis by ORCA3 and G10H overexpression might affect other metabolic pathways in the plant metabolism of C. roseus. PMID:22916202

  1. Overexpression of ORCA3 and G10H in Catharanthus roseus plants regulated alkaloid biosynthesis and metabolism revealed by NMR-metabolomics.

    Directory of Open Access Journals (Sweden)

    Qifang Pan

    Full Text Available In order to improve the production of the anticancer dimeric indole alkaloids in Catharanthuse roseus, much research has been dedicated to culturing cell lines, hairy roots, and efforts to elucidate the regulation of the monoterpenoid indole alkaloid (MIA biosynthesis. In this study, the ORCA3 (Octadecanoid-derivative Responsive Catharanthus AP2-domain gene alone or integrated with the G10H (geraniol 10-hydroxylase gene were first introduced into C. roseus plants. Transgenic C. roseus plants overexpressing ORCA3 alone (OR lines, or co-overexpressing G10H and ORCA3 (GO lines were obtained by genetic modification. ORCA3 overexpression induced an increase of AS, TDC, STR and D4H transcripts but did not affect CRMYC2 and G10H transcription. G10H transcripts showed a significant increase under G10H and ORCA3 co-overexpression. ORCA3 and G10H overexpression significantly increased the accumulation of strictosidine, vindoline, catharanthine and ajmalicine but had limited effects on anhydrovinblastine and vinblastine levels. NMR-based metabolomics confirmed the higher accumulation of monomeric indole alkaloids in OR and GO lines. Multivariate data analysis of (1H NMR spectra showed change of amino acid, organic acid, sugar and phenylpropanoid levels in both OR and GO lines compared to the controls. The result indicated that enhancement of MIA biosynthesis by ORCA3 and G10H overexpression might affect other metabolic pathways in the plant metabolism of C. roseus.

  2. Pyridine alkaloids from Senna multijuga as acetylcholinesterase inhibitors.

    Science.gov (United States)

    Francisco, Welington; Pivatto, Marcos; Danuello, Amanda; Regasini, Luis O; Baccini, Luciene R; Young, Maria C M; Lopes, Norberto P; Lopes, João L C; Bolzani, Vanderlan S

    2012-03-23

    As part of an ongoing research project on Senna and Cassia species, five new pyridine alkaloids, namely, 12'-hydroxy-7'-multijuguinol (1), 12'-hydroxy-8'-multijuguinol (2), methyl multijuguinate (3), 7'-multijuguinol (4), and 8'-multijuguinol (5), were isolated from the leaves of Senna multijuga (syn. Cassiamultijuga). Their structures were elucidated on the basis of spectroscopic data analysis. Mass spectrometry was used for confirmation of the positions of the hydroxy groups in the side-chains of 1, 2, 4, and 5. All compounds exhibited weak in vitro acetylcholinesterase inhibitory activity as compared with the standard compound physostigmine.

  3. Ampullosine, a new isoquinoline alkaloid from Sepedonium ampullosporum (Ascomycetes).

    Science.gov (United States)

    Quang, Dang Ngoc; Schmidt, Jürgen; Porzel, Andrea; Wessjohann, Ludger; Haid, Mark; Arnold, Norbert

    2010-06-01

    A new isoquinoline alkaloid, ampullosine (3-methyl-isoquinoline-6-carboxylic acid, 1), was isolated from Sepedonium ampullosporum and characterized by spectroscopic analysis and chemical reactions. This compound is responsible for the deep yellow color of the culture fluid of this species. Moreover, the known compounds sepedonin (2) and anhydrosepedonin (3) were detected. Twelve strains belonging to eight species of Sepedonium have been screened for these three metabolites by LC/ESI-SRM (selected reaction monitoring). Ampullosine (1) could be detected in almost all species in Sepedonium, but not in the phylogenetically more distant species S. brunneum and S. tulasneanum. Anhydrosepedonin (3) showed antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum. PMID:20614812

  4. Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus.

    Science.gov (United States)

    Zhao, W; Wolfender, J L; Hostettmann, K; Xu, R; Qin, G

    1998-01-01

    From the root bark of Dictamnus dasycarpus (Rutaceae), four limonoid derivatives, two furoquinoline alkaloids, five limonoids, two sesquiterpenes and three steroids were isolated and their structures elucidated on the basis of various spectroscopic methods. Among the identified compounds, one was determined to be a new natural product, 6 beta-hydroxyfraxinellone, while six compounds were found to be active against the plant pathogenic fungus Cladosporium cucumerinum. The relationship between the structures of limonoid derivatives and their inhibitory activity against fungal growth was investigated. PMID:9429316

  5. 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)

  6. Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus.

    Science.gov (United States)

    Zhu, Jianhua; Wang, Mingxuan; Wen, Wei; Yu, Rongmin

    2015-01-01

    Catharanthus roseus produces a wide range of terpenoid indole alkaloids (TIA). Many of them, such as vinblastine and vincristine, have significant bioactivity. They are valuable chemotherapy drugs used in combination with other drugs to treat lymphoma and leukemia. The TIA biosynthetic pathway has been investigated for many years, for scientific interest and for their potential in manufacturing applications, to fulfill the market demand. In this review, the progress and perspective of C. roseus TIA biosynthesis and its regulating enzymes are described. In addition, the culture condition, hormones, signaling molecules, precursor feeding on the accumulation of TIA, and gene expression are also evaluated and discussed. PMID:26009689

  7. Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus

    Directory of Open Access Journals (Sweden)

    Jianhua Zhu

    2015-01-01

    Full Text Available Catharanthus roseus produces a wide range of terpenoid indole alkaloids (TIA. Many of them, such as vinblastine and vincristine, have significant bioactivity. They are valuable chemotherapy drugs used in combination with other drugs to treat lymphoma and leukemia. The TIA biosynthetic pathway has been investigated for many years, for scientific interest and for their potential in manufacturing applications, to fulfill the market demand. In this review, the progress and perspective of C. roseus TIA biosynthesis and its regulating enzymes are described. In addition, the culture condition, hormones, signaling molecules, precursor feeding on the accumulation of TIA, and gene expression are also evaluated and discussed.

  8. 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)

  9. A New Prenylated Indole Diketopiperazine Alkaloid from Eurotium cristatum

    Directory of Open Access Journals (Sweden)

    Xianwei Zou

    2014-11-01

    Full Text Available A new prenylated indole diketopiperazine alkaloid, cristatumin F (1, and four known metabolites, echinulin (2, dehydroechinulin (3, neoechinulin A (4 and variecolorin O (5, were isolated from the crude extract of the fungus Eurotium cristatum. The structure of 1 was elucidated primarily by NMR and MS methods. The absolute configuration of 1 was assigned using Marfey’s method applied to its acid hydrolyzate. Cristatumin F (1 showed modest radical scavenging activity against DPPH radicals, and exhibited marginal attenuation of 3T3L1 pre-adipocytes.

  10. A new prenylated indole diketopiperazine alkaloid from Eurotium cristatum.

    Science.gov (United States)

    Zou, Xianwei; Li, Ying; Zhang, Xiaona; Li, Qian; Liu, Xuan; Huang, Yun; Tang, Tao; Zheng, Saijing; Wang, Weimiao; Tang, Jintian

    2014-11-03

    A new prenylated indole diketopiperazine alkaloid, cristatumin F (1), and four known metabolites, echinulin (2), dehydroechinulin (3), neoechinulin A (4) and variecolorin O (5), were isolated from the crude extract of the fungus Eurotium cristatum. The structure of 1 was elucidated primarily by NMR and MS methods. The absolute configuration of 1 was assigned using Marfey's method applied to its acid hydrolyzate. Cristatumin F (1) showed modest radical scavenging activity against DPPH radicals, and exhibited marginal attenuation of 3T3L1 pre-adipocytes.

  11. Scientific Opinion on Ergot alkaloids in food and feed

    OpenAIRE

    EFSA Panel on Contaminants in the Food Chain (CONTAM)

    2012-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread Claviceps species within the Hypocreales. A total of 20 558 analytical results for EAs in 1 716 food, 496 feed and 67 unprocessed grain samples wer...

  12. 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 ...... to afford the desired calystegines. Hereby, calystegine B2, B3, and B4 are prepared from D-glucose, D-galactose, and D-mannose, respectively. This route constitutes the shortest synthesis of calystegine B2 and gives rise to the first total syntheses of calystegine B3 and B4....

  13. INHIBITORY EFFECTS OF THE ALKALOIDS FROM Radix Caulophylli ON THE PROLIFERATION OF HUMAN VASCULAR ENDOTHELIAL CELL

    Institute of Scientific and Technical Information of China (English)

    2005-01-01

    Objective To find an angiogenetic inhibitor from Radix Caulophylli (RC). Methods The extract of Radix Caulophylli was obtained by using 95% alcohol in water as solvent. Then, the total alkaloids of Radix Caulophylli was isolated from the extract by using a positive ion exchange resin column. An active part was found by a screening model of cell membrane chromatography (CMC) and further tested by the MTT method with emodin as a control. Results The total alkaloids of Radix Caulophylli was the active part by CMC and could significantly inhibit proliferation of ECV304 cells in MTT test. The inhibitory rate was 56.06% while the concentration of the total alkaloids of Radix Caulophylli was 19.63μg/mL. Conclusion The total alkaloids from Radix Caulophylli may be a new angiogenetic inhibitor, and mechanism of the total alkaloids on inhibitory angiogenesis still need to be further investigated.

  14. Alkaloids Induce Programmed Cell Death in Bloodstream Forms of Trypanosomes (Trypanosoma b. brucei

    Directory of Open Access Journals (Sweden)

    Michael Wink

    2008-10-01

    Full Text Available The potential induction of a programmed cell death (PCD in Trypanosoma b. brucei by 55 alkaloids of the quinoline, quinolizidine, isoquinoline, indole, terpene, tropane, steroid, and piperidine type was studied by measuring DNA fragmentation and changes in mitochondrial membrane potential. For comparison, the induction of apoptosis by the same alkaloids in human leukemia cells (Jurkat APO-S was tested. Several alkaloids of the isoquinoline, quinoline, indole and steroidal type (berberine, chelerythrine, emetine, sanguinarine, quinine, ajmalicine, ergotamine, harmine, vinblastine, vincristine, colchicine, chaconine, demissidine and veratridine induced programmed cell death, whereas quinolizidine, tropane, terpene and piperidine alkaloids were mostly inactive. Effective PCD induction (EC50 below 10 µM was caused in T. brucei by chelerythrine, emetine, sanguinarine, and chaconine. The active alkaloids can be characterized by their general property to inhibit protein biosynthesis, to intercalate DNA, to disturb membrane fluidity or to inhibit microtubule formation.

  15. Differential alkaloid profile in Uncaria tomentosa micropropagated plantlets and root cultures.

    Science.gov (United States)

    Luna-Palencia, Gabriela R; Huerta-Heredia, Ariana A; Cerda-García-Rojas, Carlos M; Ramos-Valdivia, Ana C

    2013-05-01

    The alkaloids of Uncaria tomentosa micropropagated plantlets and root cultures were isolated and identified by NMR and mass spectrometry. Plantlets yielded pteropodine (1), isopteropodine (2), mitraphylline (3), isomitraphylline (4), uncarine F (5), speciophylline (6), rhynchophylline (7) and isorhynchophylline (8). In plantlets growing under continuous light, tetracyclic alkaloids 7 and 8 decreased from 20 ± 1.8 at 2 months to 2.2 ± 0.33 mg/g dry wt at 6 months, while the pentacyclic alkaloids 1-4 increased from 7.7 ± 1.4 to 15 ± 0.05 mg/g dry wt, supporting their biogenetic conversion. Micropropagated plantlets produced four times more alkaloids (27.6 ± 3.1 mg/g dry wt) than greenhouse plants. Plantlet roots yielded 3, 4, 8 and the glucoindole alkaloids 3α-dihydrocadambine (9) and dolichantoside (10), the last one not previously found in Uncaria.

  16. Bioactive heterocyclic alkaloids with diterpene structure isolated from traditional Chinese medicines.

    Science.gov (United States)

    Xu, Tengfei; Liu, Shu; Meng, Lulu; Pi, Zifeng; Song, Fengrui; Liu, Zhiqiang

    2016-07-15

    The diterpenoid alkaloids as one type of heterocyclic alkaloids have been found in many traditional herbal medicines, such as genus Consolida, Aconitum, and Delphinium (Ranunculaceae). Pharmacological researches have indicated that many diterpenoid alkaloids are the main bioactive components which have analgesic, anti-inflammatory, anti-microbial, anti-tumor, cardiotonic, and anti-arrhythmic activities. Studies focused on the determination, quantitation and pharmacological properties of these alkaloids have dramatically increased during the past few years. Up to now, newly discovered diterpenoid alkaloids with important biological activities have been isolated and synthesized. Considering their significant role and diffusely used in many disease treatments, we summarized the information of their analysis methods, bioactivity, metabolism and biotransformation in vivo as well as the pharmacological mechanisms. Based on above review, the further researches are suggested.

  17. Hypolipidemic Effects of Alkaloids from Rhizoma Coptidis in Diet-Induced Hyperlipidemic Hamsters.

    Science.gov (United States)

    He, Kai; Kou, Shuming; Zou, Zongyao; Hu, Yinran; Feng, Min; Han, Bing; Li, Xuegang; Ye, Xiaoli

    2016-05-01

    This study was conducted to evaluate the antihyperlipidemic activity of five major alkaloids in Rhizoma Coptidis using high-fat- and high-cholesterol-induced hyperlipidemic hamsters. Hyperlipidemic hamsters were treated with coptisine, berberine, jatrorrhizine, palmatine, epiberberine, and total Rhizoma Coptidis alkaloids with a dose of 46.7 mg/kg × day for 140 days. Serum total cholesterol, triglyceride, high-density lipoprotein cholesterol, low-density lipoprotein cholesterol, and total bile acids were examined after alkaloid treatment. The results showed that all therapy agents prevented body weight gain, reduced the serum total cholesterol, and increased the high-density lipoprotein cholesterol of hamsters. Berberine, jatrorrhizine, and total Rhizoma Coptidis alkaloids decreased the triglyceride level in hyperlipidemic hamsters, while coptisine, jatrorrhizine, palmatine, and total Rhizoma Coptidis alkaloids significantly suppressed the elevation of the low-density lipoprotein cholesterol level. The fecal excretion of bile acids was significantly elevated by berberine, coptisine, jatrorrhizine, palmatine, total Rhizoma Coptidis alkaloids, and orlistat. Notably, total Rhizoma Coptidis alkaloids possess a much stronger lipid-lowering effect than the pure Rhizoma Coptidis alkaloids. Quantitative reverse transcription-polymerase chain reaction analyses revealed that Rhizoma Coptidis alkaloids could retard the synthesis of cholesterol by downregulating the mRNA expression of 3-hydroxy-3-methyl glutaryl coenzyme A reductase and accelerate the clearance of lipids by upregulating the low-density lipoprotein receptor, cholesterol 7α-hydroxylase, and uncoupling protein-2 expression. These findings highlight the critical role of Rhizoma Coptidis alkaloids in hyperlipidemia treatment. Thus, they need to be considered in future therapeutic approaches. PMID:26848702

  18. Acridone alkaloids as potent inhibitors of cathepsin V.

    Science.gov (United States)

    Severino, Richele P; Guido, Rafael V C; Marques, Emerson F; Brömme, Dieter; da Silva, M Fátima das G F; Fernandes, João B; Andricopulo, Adriano D; Vieira, Paulo C

    2011-02-15

    Cathepsin V is a lysosomal cysteine peptidase highly expressed in thymus, testis and corneal epithelium. Eleven acridone alkaloids were isolated from Swinglea glutinosa (Bl.) Merr. (Rutaceae), with eight of them being identified as potent and reversible inhibitors of cathepsin V (IC(50) values ranging from 1.2 to 3.9 μM). Detailed mechanistic characterization of the effects of these compounds on the cathepsin V-catalyzed reaction showed clear competitive inhibition with respect to substrate, with dissociation constants (K(i)) in the low micromolar range (2, K(i)=1.2 μM; 6, K(i)=1.0 μM; 7, K(i)=0.2 μM; and 11, K(i)=1.7 μM). Molecular modeling studies provided important insight into the structural basis for binding affinity and enzyme inhibition. Experimental and computational approaches, including biological evaluation, mode of action assessment and modeling studies were successfully employed in the discovery of a small series of acridone alkaloid derivatives as competitive inhibitors of catV. The most potent inhibitor (7) has a K(i) value of 200 nM. PMID:21277783

  19. Plant-like biosynthesis of isoquinoline alkaloids in Aspergillus fumigatus.

    Science.gov (United States)

    Baccile, Joshua A; Spraker, Joseph E; Le, Henry H; Brandenburger, Eileen; Gomez, Christian; Bok, Jin Woo; Macheleidt, Juliane; Brakhage, Axel A; Hoffmeister, Dirk; Keller, Nancy P; Schroeder, Frank C

    2016-06-01

    Natural product discovery efforts have focused primarily on microbial biosynthetic gene clusters (BGCs) containing large multimodular polyketide synthases and nonribosomal peptide synthetases; however, sequencing of fungal genomes has revealed a vast number of BGCs containing smaller NRPS-like genes of unknown biosynthetic function. Using comparative metabolomics, we show that a BGC in the human pathogen Aspergillus fumigatus named fsq, which contains an NRPS-like gene lacking a condensation domain, produces several new isoquinoline alkaloids known as the fumisoquins. These compounds derive from carbon-carbon bond formation between two amino acid-derived moieties followed by a sequence that is directly analogous to isoquinoline alkaloid biosynthesis in plants. Fumisoquin biosynthesis requires the N-methyltransferase FsqC and the FAD-dependent oxidase FsqB, which represent functional analogs of coclaurine N-methyltransferase and berberine bridge enzyme in plants. Our results show that BGCs containing incomplete NRPS modules may reveal new biosynthetic paradigms and suggest that plant-like isoquinoline biosynthesis occurs in diverse fungi. PMID:27065235

  20. Excretion of alkaloids by malpighian tubules of insects.

    Science.gov (United States)

    Maddrell, S H; Gardiner, B O

    1976-04-01

    Nicotine is transported at high rates by Malpighian tubules of larvae of Manduca sexta, Pieris brassicae and Rhodnius prolixus and the transport persists in the absence of alkaloid from the diet. In the fluid-secreting portion of Rhodnius tubules this transport is not coupled to ion transport, nor is it dependent on the physiological state of the animal. The transport, which can occur against a steep electrochemical gradient, shows saturation kinetics with a maximal rate of 700 pmol. min-1 per tubule and is half saturated at 2-3 mM. Nicotine transport independent of ion movements also occurs in the lower resorptive parts of Rhodnius tubules. Both portions of Rhodnius tubules can transport morphine and atropine. These alkaloids and nicotine compete with one naother and are presumed to be carried by the smae transport system. Nicotine transport in Rhodnius was unaffected by organic anions, such as amaranth and benzyl penicillin, or by the organic anion transport inhibitor, probenecid. Fluid secretion in 5-HT-stimulated tubules was reduced by atropine and nicotine, probably by blocking the 5-HT receptors. The Malpighian tubules of adult Calliphora erythrocephala and Musca domestica remove nicotine from bathing solutions, an unknown metabolic accumulating in the tubules. Adult P. brassicae and M. sexta do not exhibit transport of nicotine by their Malpighian tubules.

  1. Catharanthus roseus (L. G. Don - plant regeneration and alkaloids content

    Directory of Open Access Journals (Sweden)

    Mirosława Furmanowa

    2014-02-01

    Full Text Available We describe here a regeneration of plantlets of Catharanthus roseus (L. G. Don from shoot tips and axillary buds. Shoot tips were excised from 7-day-old seedlings and were incubated in solid Nitsch and Nitsch (NN medium supplemented with kinetin, benzyladenine (BA, indole-3-butyric acid (IBA and β-indolylacetic acid (IAA in various combinations. After two months in culture, regenerated rooted plantlets were cut and transferred to a new medium; the explants contained shoot tips or axillary buds. Four passages were done. We obtained about 200 rooting plantlets from one seedling. Then the plantlets were transferred to the soil and they grew under a foil tent. After five months of vegetation they were collected, dried and weighed. Chemical investigations of leaves of these plants were done. The vindoline and catharanthine were dominant alkaloids in the juvenile stage of plants (before blooming. Total amount of alkaloids, equal 2.95%, was gravimetrically determined in leaves of plants, after 4th passage, regenerated in vitro on NN medium supplemented with kinetin and IBA.

  2. Biosynthetic pathway of terpenoid indole alkaloids in Catharanthus roseus.

    Science.gov (United States)

    Zhu, Xiaoxuan; Zeng, Xinyi; Sun, Chao; Chen, Shilin

    2014-09-01

    Catharanthus roseus is one of the most extensively investigated medicinal plants, which can produce more than 130 alkaloids, including the powerful antitumor drugs vinblastine and vincristine. Here we review the recent advances in the biosynthetic pathway of terpenoid indole alkaloids (TIAs) in C. roseus, and the identification and characterization of the corresponding enzymes involved in this pathway. Strictosidine is the central intermediate in the biosynthesis of different TIAs, which is formed by the condensation of secologanin and tryptamine. Secologanin is derived from terpenoid (isoprenoid) biosynthetic pathway, while tryptamine is derived from indole biosynthetic pathway. Then various specific end products are produced by different routes during downstream process. Although many genes and corresponding enzymes have been characterized in this pathway, our knowledge on the whole TIA biosynthetic pathway still remains largely unknown up to date. Full elucidation of TIA biosynthetic pathway is an important prerequisite to understand the regulation of the TIA biosynthesis in the medicinal plant and to produce valuable TIAs by synthetic biological technology. PMID:25159992

  3. New cycloartane saponin and monoterpenoid glucoindole alkaloids from Mussaenda luteola

    Science.gov (United States)

    Mohamed, Shaymaa M.; Backheet, Enaam Y.; Bayoumi, Soad A.; Ross, Samir A.

    2016-01-01

    A new cycloartane-type saponin with unusual hydroxylation at C-17 and a unique side chain, 9 (R), 19, 22 (S), 24 (R) bicyclolanost-3β, 12α, 16β, 17α tetrol-25-one 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (1) and two new monoterpenoid glucoindole alkaloids, 10-methoxy pumiloside (2) and the previously chemically synthesized, 10-methoxy strictosidine (3) along with other five known compounds, 7α-morroniside (4), 7-epi-loganin (5), (7β)-7-O-methylmorroniside (6), 5(S)-5-carboxystrictisidine (7) and apigenin-7-O-neohesperidoside (8) were isolated from the aerial parts of Mussaenda luteola (Rubiaceae). The structural elucidation of the isolates was accomplished by extensive (1D and 2D NMR) spectroscopic data analysis and HR-ESI-MS. Compounds 4–8 were reported for the first time from the genus Mussaenda. Interestingly, this is the first report for the occurrence of the monoterpenoid glucoindole-type alkaloids in the genus which might be useful for the chemotaxonomic evaluation of the genus Mussaenda. All isolates were evaluated for their antiprotozoal activities. Compound 7 showed good antitrypanosomal activity with IC50 and IC90 values of 13.7 and 16.6 µM compared to IC50 and IC90 values of 13.06 and 28.99 µM for the positive control DFMO, difluoromethylornithine. PMID:26969788

  4. New cycloartane saponin and monoterpenoid glucoindole alkaloids from Mussaenda luteola.

    Science.gov (United States)

    Mohamed, Shaymaa M; Backheet, Enaam Y; Bayoumi, Soad A; Ross, Samir A

    2016-04-01

    A new cycloartane-type saponin with unusual hydroxylation at C-17 and a unique side chain, 9 (R), 19, 22 (S), 24 (R) bicyclolanost-3β, 12α, 16β, 17α tetrol-25-one 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (1) and two new monoterpenoid glucoindole alkaloids, 10-methoxy pumiloside (2) and the previously chemically synthesized, 10-methoxy strictosidine (3) along with other five known compounds, 7α-morroniside (4), 7-epi-loganin (5), (7β)-7-O-methylmorroniside (6), 5(S)-5-carboxystrictisidine (7) and apigenin-7-O-neohesperidoside (8) were isolated from the aerial parts of Mussaenda luteola (Rubiaceae). The structural elucidation of the isolates was accomplished by extensive (1D and 2D NMR) spectroscopic data analysis and HR-ESI-MS. Compounds 4-8 were reported for the first time from the genus Mussaenda. Interestingly, this is the first report for the occurrence of the monoterpenoid glucoindole-type alkaloids in the genus which might be useful for the chemotaxonomic evaluation of the genus Mussaenda. All isolates were evaluated for their antiprotozoal activities. Compound 7 showed good antitrypanosomal activity with IC50 and IC90 values of 13.7 and 16.6 μM compared to IC50 and IC90 values of 13.06 and 28.99 μM for the positive control DFMO, difluoromethylornithine. PMID:26969788

  5. The distribution of inole alkaloids in different organs of Catharanthus roseus G. Don. (Vinca rosea L

    Directory of Open Access Journals (Sweden)

    Hassan Ebrahimzadeh

    1996-08-01

    Full Text Available The study of alkaloid extract of the leaf of Vinca rosea by TLC showed the existence of 13 bands, 7 bands of them were: Serpentine, Vincristine, Vinblastine, Ajmaline, Catharantine, Vindoline and Ajmalicine. The existence of these 7 alkaloids was confirmed in the young leaves, old leaves and the roots of the plant by HPLC. Furthermore, two alkaloids with the short retention times and one alkaloid with the medium retention time in the young leaf, three alkaloids with the short retention time and one alkaloid with long retention time in the old leaf, and one alkaioid with the short retention time and two other alkaloids with the long retention times in the root, were observed."nThe study of absorption spectrum of alkaloid extract and its comparison with absorption spectrum of ajmalicine showed that the latter can be used for drawing a standard curve and detecting the amount of total alkaloids. The total alkaloids in fresh root, old leaf and young leaf were 2.1 mg , 1.3 mg and 0.9 mg/g respectively, Vindoline and Catharantine were major alkaloids in all of them. However, their amount were more in the root (1.2 mg/ g of fresh material, 0.85 in the old leaf and 0.38 in the young leaf. Vinblastine existed in all three samples but its amount was more in the root {0.22 mg per gramme of the fresh material in the root, 0.26 in the young leaf and 0.003 in the old leaf."nAjmalicine was detected only in the leaf and its amount was more in young leaf than the old leaf (0.141 mg/g of the fresh material in the young leaf and 0.013 in the old leaf. Serpentine was seen in all of the studied organs but its amount was more in the young leaf than other organs (0.192 mg/ g of the fresh material in the young leaf, 0.11 in the root and 0.07 in the old leaf. Ajmaline existed in all of the organs in minute amount but in the old leaf was more (0 .07 mg/g of the fresh material in the old !eaf,0.044 in the young leaf and 0.04 in the root . The percentage of unknown

  6. Alkaloids: an overview of their antibacterial, antibiotic-enhancing and antivirulence activities.

    Science.gov (United States)

    Cushnie, T P Tim; Cushnie, Benjamart; Lamb, Andrew J

    2014-11-01

    With reports of pandrug-resistant bacteria causing untreatable infections, the need for new antibacterial therapies is more pressing than ever. Alkaloids are a large and structurally diverse group of compounds that have served as scaffolds for important antibacterial drugs such as metronidazole and the quinolones. In this review, we highlight other alkaloids with development potential. Natural, semisynthetic and synthetic alkaloids of all classes are considered, looking first at those with direct antibacterial activity and those with antibiotic-enhancing activity. Potent examples include CJ-13,136, a novel actinomycete-derived quinolone alkaloid with a minimum inhibitory concentration of 0.1 ng/mL against Helicobacter pylori, and squalamine, a polyamine alkaloid from the dogfish shark that renders Gram-negative pathogens 16- to >32-fold more susceptible to ciprofloxacin. Where available, information on toxicity, structure-activity relationships, mechanisms of action and in vivo activity is presented. The effects of alkaloids on virulence gene regulatory systems such as quorum sensing and virulence factors such as sortases, adhesins and secretion systems are also described. The synthetic isoquinoline alkaloid virstatin, for example, inhibits the transcriptional regulator ToxT in Vibrio cholerae, preventing expression of cholera toxin and fimbriae and conferring in vivo protection against intestinal colonisation. The review concludes with implications and limitations of the described research and directions for future research. PMID:25130096

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

    International Nuclear Information System (INIS)

    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 14C 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)

  8. Effect of polyamine biosynthetic inhibitors on alkaloids and organogenesis in tobacco callus cultures.

    Science.gov (United States)

    Tiburcio, A F; Kaur-Sawhney, R; Galston, A W

    1987-01-01

    We studied the effects of inhibitors of ornithine decarboxylase (ODC), arginine decarboxylase (ADC) and spermidine synthase (Spd synthase) on organogenesis and the titers of polyamines (PA) and alkaloids in tobacco calli. DL-alpha-diffluromethylarginine (DFMA) and D-arginine (D-Arg), both inhibitors of ADC activity, were more effective than DL-alpha-difluromethylorinithine (DFMO), an inhibitor of ODC, in reducing titers of PA and the putrescine (Put)-derived alkaloids (nornicotine and nicotine). Dicyclohexylammonium sulfate (DCHA), an inhibitor of Spd synthase, was also more efficient than DFMO in reducing PA and alkaloid levels. Root organogenesis is inversely related to the titers of Put and alkaloids. Thus, DFMA and D-Arg, which strongly inhibit Put and alkaloid biosynthesis, markedly promote root organogenesis, while control callus with high Put and alkaloid content showed poor root organization. These results suggest that morphological differentiation is not required for activation of secondary metabolic pathways and support the view that ADC has a major role in the generation of Put going to the pyrrolidine ring of tobacco alkaloids.

  9. HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus

    Directory of Open Access Journals (Sweden)

    Paulo Mazzafera

    2008-07-01

    Full Text Available Pilocarpine, an important imidazole alkaloid, is extracted from the leaves of Pilocarpus microphyllus (Rutaceae, known in Brazil as jaborandi and used mainly for the treatment of glaucoma. Jaborandi leaves also contain other imidazole alkaloids, whose pharmacological and physiological properties are unknown, and whose biosynthetic pathways are under investigation. In the present study, a HPLC method coupled with ESI-MSn was developed for their qualitative and quantitative analysis. This method permits the chromatographic separation of the imidazole alkaloids found in extracts of jaborandi, as well as the MS/MS analysis of the individual compounds. Thus two samples: leaves of P. microphyllus and a paste that is left over after the industrial extraction of pilocarpine; were compared. The paste was found to contain significant amounts of pilocarpine and other imidazole alkaloids, but had a slightly different alkaloid profile than the leaf extract. The method is suitable for the routine analysis of samples containing these alkaloids, as well as for the separation and identification of known and novel alkaloids from this family, and may be applied to further studies of the biosynthetic pathway of pilocarpine in P. microphyllus.

  10. HPLC-ESI-MS/MS of imidazole alkaloids in Pilocarpus microphyllus.

    Science.gov (United States)

    Sawaya, Alexandra C H F; Abreu, Ilka Nacif; Andreazza, Nathalia Luiza; Eberlin, Marcos N; Mazzafera, Paulo

    2008-01-01

    Pilocarpine, an important imidazole alkaloid, is extracted from the leaves of Pilocarpus microphyllus (Rutaceae), known in Brazil as jaborandi and used mainly for the treatment of glaucoma. Jaborandi leaves also contain other imidazole alkaloids, whose pharmacological and physiological properties are unknown, and whose biosynthetic pathways are under investigation. In the present study, a HPLC method coupled with ESI-MS(n) was developed for their qualitative and quantitative analysis. This method permits the chromatographic separation of the imidazole alkaloids found in extracts of jaborandi, as well as the MS/MS analysis of the individual compounds. Thus two samples: leaves of P. microphyllus and a paste that is left over after the industrial extraction of pilocarpine; were compared. The paste was found to contain significant amounts of pilocarpine and other imidazole alkaloids, but had a slightly different alkaloid profile than the leaf extract. The method is suitable for the routine analysis of samples containing these alkaloids, as well as for the separation and identification of known and novel alkaloids from this family, and may be applied to further studies of the biosynthetic pathway of pilocarpine in P. microphyllus. PMID:18719522

  11. 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.

  12. Asexual endophytes in a native grass: tradeoffs in mortality, growth, reproduction, and alkaloid production.

    Science.gov (United States)

    Faeth, Stanley H; Hayes, Cinnamon J; Gardner, Dale R

    2010-10-01

    Neotyphodium endophytes are asexual, seed-borne fungal symbionts that are thought to interact mutualistically with their grass hosts. Benefits include increased growth, reproduction, and resistance to herbivores via endophytic alkaloids. Although these benefits are well established in infected introduced, agronomic grasses, little is known about the cost and benefits of endophyte infection in native grass populations. These populations exist as mosaics of uninfected and infected plants, with the latter often comprised of plants that vary widely in alkaloid content. We tested the costs and benefits of endophyte infections with varying alkaloids in the native grass Achnatherum robustum (sleepygrass). We conducted a 4-year field experiment, where herbivory and water availability were controlled and survival, growth, and reproduction of three maternal plant genotypes [uninfected plants (E-), infected plants with high levels of ergot alkaloids (E+A+), and infected plants with no alkaloids (E+A-)] were monitored over three growing seasons. Generally, E+A+ plants had reduced growth over the three growing seasons and lower seed production than E- or E+A- plants, suggesting a cost of alkaloid production. The reduction in vegetative biomass in E+A+ plants was most pronounced under supplemented water, contrary to the prediction that additional resources would offset the cost of alkaloid production. Also, E+A+ plants showed no advantage in growth, seed production, or reproductive effort under full herbivory relative to E- or E+A- grasses, contrary to the predictions of the defensive mutualism hypothesis. However, E+A+ plants had higher overwintering survival than E+A- plants in early plant ontogeny, suggesting that alkaloids associated with infection may protect against below ground herbivory or harsh winter conditions. Our results suggest that the mosaic of E-, E+A+, and E+A- plants observed in nature may result from varying biotic and abiotic selective factors that maintain

  13. Preparation and in vitro evaluation of ethosomal total alkaloids of Sophora alopecuroides loaded by a transmembrane pH-gradient method.

    Science.gov (United States)

    Zhou, Yan; Wei, Yuhui; Liu, Huanxiang; Zhang, Guoqiang; Wu, Xin'an

    2010-09-01

    A novel transmembrane pH gradient active loading method to prepare alkaloids binary ethosomes was developed in this work. Using this novel method, binary ethosomes containing total alkaloids extracted from Sophora alopecuroides (TASA) were prepared successfully at the temperature below the phase transition temperature (Tc) of the phosphatidyl choline (PC). Several factors affecting this method were investigated. The qualities of the TASA binary ethosomes were characterized by the shape, particle size, and encapsulation efficiency (EE). The percutaneous absorption study of TASA binary ethosomes was performed using confocal laser scanning microscopy and Franz diffusion cells. The results showed that more than 90% sophoridine, 47% matrine, 35% sophocarpine, and 32% lemannine in TASA were entrapped within 1 h at 40°C, with an efficiency improvement of 8.87, 8.10, 7.63, and 7.78-fold than those observed in passive loading method. Transdermal experiments showed that the penetration depth and fluorescence intensity of Rhodamine B from binary ethosome prepared by pH gradient active loading method were much greater than that from binary ethosome prepared by passive loading method or hydroalcoholic solution. These results suggested transmembrane pH gradient active loading method may be an effective method to prepare alkaloids ethosomal systems at the temperatures below the Tc of PC.

  14. Genotoxicity of the boldine aporphine alkaloid in prokaryotic and eukaryotic organisms.

    Science.gov (United States)

    Moreno, P R; Vargas, V M; Andrade, H H; Henriques, A T; Henriques, J A

    1991-06-01

    The aporphine alkaloid boldine, present in Peumus boldus (boldo-do-Chile) widely used all over the world, was tested for the presence of genotoxic, mutagenic and recombinogenic activities in microorganisms. This alkaloid did not show genotoxic activity with or without metabolic activation in the SOS chromotest and Ames tester strains TA100, TA98 and TA102. It was not able to induce point and frameshift mutations in haploid Saccharomyces cerevisiae cells. However, mitotic recombinational events such as crossing-over and gene conversion were weakly induced in diploid yeast cells by this alkaloid. Also, boldine was able to induce weakly cytoplasmic 'petite' mutation in haploid yeast cells. PMID:2046695

  15. [HPTLC separation and fluorodensitometric determination of isoquinoline alkaloids in Chelidonine majus L].

    Science.gov (United States)

    Niu, C Q; He, L Y

    1992-01-01

    The quantitative analysis of isoquinoline alkaloids in Chelidonine majus L. was investigated and a HPTLC method has been established. Using this method, we separated and determined eight isoquinoline alkaloids, i.e. chelidonine, protopine, berberine, coptisine, tetrahydrocoptisine, 6-methoxydihydrochelerythrine, 6-methoxydihydrosanguinarine and dihydrosanguinarine. The HPTLC method developed used one developing system on high performance silica gel plate (10 x 10 cm). After separation of these eight alkaloids, fluorescence derivatization was carried out in situ. The content was determined by fluorescence scanning. TLC fluorescence derivatization, fluorescence enhancement and fluorescence stability have been studied. Experiments showed that this method is simple, fast, highly sensitive and highly selective. PMID:1529718

  16. Neonaucline, a New Indole Alkaloid from the Leaves of Ochreinauclea maingayii (Hook. f. Ridsd. (Rubiaceae

    Directory of Open Access Journals (Sweden)

    Marc Litaudon

    2011-12-01

    Full Text Available A new indole alkaloid; neonaucline (1, along with six known compounds–Cadamine (2, naucledine (3, harmane, benzamide, cinnamide and blumenol A–were isolated from the leaves of Ochreinauclea maingayii (Rubiaceae. In addition to that of compound 1, 13C-NMR data of cadamine (2 and naucledine (3 were also reported. Structural elucidations of these alkaloids were performed using spectroscopic methods especially 1D- and 2D-NMR, IR, UV and LCMS-IT-TOF. The excellent vasorelaxant activity on isolated rat aorta was observed for the alkaloids 1–3 after injection of each sample at 1 × 10−5 M.

  17. GC-MS investigation of Amaryllidaceae alkaloids in Galanthus xvalentinei nothosubsp. subplicatus.

    Science.gov (United States)

    Sarikaya, Buket Bozkurt; Berkov, Strahil; Bastida, Jaume; Kaya, Gulen Irem; Onur, Mustafa Ali; Somer, Nehir Unver

    2013-03-01

    A GC-MS analysis of alkaloids in the aerial parts and bulbs of Galanthus xvalentinei nothosubsp. subplicatus was performed for the first time. Totally, twenty-six alkaloids were identified, of which tazettine and galanthindole were the major ones. Acetylcholinesterase inhibitory activity of the alkaloidal extracts was determined using modified in vitro Ellman's method. Significant anticholinesterase activity was observed in the tested samples (bulbs: IC50 = 21.3 microg/mL, aerial parts: IC50 = 16.3 microg/mL).

  18. Weak C–H…O hydrogen bonds in alkaloids: An overview

    Indian Academy of Sciences (India)

    Rajnikant; Dinesh; Kamni

    2005-06-01

    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 those alkaloids whose three-dimensional structure has been reported by us. The C–H…O hydrogen bonding in the solid state in alkaloids has been found to be predominant and this observation makes the role of hydrogen bonding in organic molecular assemblies very important.

  19. Alkaloids from Marine Invertebrates as Important Leads for Anticancer Drugs Discovery and Development

    Directory of Open Access Journals (Sweden)

    Concetta Imperatore

    2014-12-01

    Full Text Available The present review describes research on novel natural antitumor alkaloids isolated from marine invertebrates. The structure, origin, and confirmed cytotoxic activity of more than 130 novel alkaloids belonging to several structural families (indoles, pyrroles, pyrazines, quinolines, and pyridoacridines, together with some of their synthetic analogs, are illustrated. Recent discoveries concerning the current state of the potential and/or development of some of them as new drugs, as well as the current knowledge regarding their modes of action, are also summarized. A special emphasis is given to the role of marine invertebrate alkaloids as an important source of leads for anticancer drug discovery.

  20. Alkaloids from Duguetia flagellaris Huber (Annonaceae); Alcaloides de Duguetia flagellaris Huber (Annonaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Navarro, V.R.; Sette, I.M.F.; Da-Cunha, E.V.L.; Silva, M.S.; Barbosa Filho, J.M. [Paraiba Univ., Joao Pessoa, PB (Brazil). Lab. de Tecnologia Farmaceutica; Maia, J.G.S. [Museu Paraense Emilio Goeldi, Belem, PA (Brazil). Dept. de Botanica

    2001-04-01

    Ten aporphine alkaloids were isolated from ethanol extract of leaves, thin branches and stem bark of Duguetia flagellaris Huber (Annonceae); they were identified by {sup 1} H and {sup 13} C NMR spectroscopic techniques; five were aporphine strictu sensu: nornuciferine (1), isopiline (2), O-methylisopiline (3), calycinine (3), duguevanine (5), and five 7-hydroxyaporphines: pachypodanthine (6), oliveroline {beta}-N-oxide (8), oliveridine (9), and duguetine (10). Alkaloids 2, 6, 7 and 8 are being cited for the first time in Duguetia genus. This study also includes a literature review of the chemical constituents of the genus Duguetia, predominantly aporphine alkaloids, all isolated from plants that occur in South America. (author)

  1. Hainanerectamines A–C, Alkaloids from the Hainan Sponge Hyrtios erecta

    OpenAIRE

    Wen-Fei He; Duo-Qing Xue; Li-Gong Yao; Jing-Ya Li; Jia Li; Yue-Wei Guo

    2014-01-01

    Two new indole alkaloids, hainanerectamines A (1) and B (2), and one new β-carboline alkaloids, hainanerectamines C (4), along with five known related alkaloids (3, 5–8), have been isolated from the Hainan marine sponge Hyrtios erecta. The structures of new compounds 1, 2 and 4 were determined by detailed analysis of their 1D and 2D NMR spectra and by comparison of their spectroscopic data with those of related model compounds. Compounds 2–4 exhibited moderate inhibitory activity against Aur...

  2. Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

    Science.gov (United States)

    Li, Yanran; Smolke, Christina D.

    2016-01-01

    Noscapine is a potential anticancer drug isolated from the opium poppy Papaver somniferum, and genes encoding enzymes responsible for the synthesis of noscapine have been recently discovered to be clustered on the genome of P. somniferum. Here, we reconstitute the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates, complementing and extending previous in planta and in vitro investigations. Our work provides structural validation of the secoberberine intermediates and the description of the narcotoline-4′-O-methyltransferase, suggesting this activity is catalysed by a unique heterodimer. We also reconstitute a 14-step biosynthetic pathway of noscapine from the simple alkaloid norlaudanosoline by engineering a yeast strain expressing 16 heterologous plant enzymes, achieving reconstitution of a complex plant pathway in a microbial host. Other engineered yeasts produce previously inaccessible pathway intermediates and a novel derivative, thereby advancing protoberberine and noscapine related drug discovery. PMID:27378283

  3. New Alkaloid De-Oxypalmitine from Coscinium fenestratum

    Directory of Open Access Journals (Sweden)

    K. Talat

    2012-06-01

    Full Text Available Present study is aimed at to investigate phytochemically the stem bark of Coscinium fenestratum (family Menispermaceae a plant popularly and commonly known as “tree turmeric” used globally in traditional medicine to treat variety of ailments, using a standard procedure. Fractionation of its methanol extract by ethyl acetate and chloroform and subsequent column chromatography over silica gel G (60-120 mesh size led to the isolation of Berberine, Palmitine and Jatrorrhizine. The structure of palmitine was elucidated using 1H-NMR, 13C-NMR, FABMS and DEPT analysis and was confirmed. In addition, alkaloid Deoxypalmitine (1 was isolated from the methanol extract of the defatted stem of the Coscinium fenestratum. The structure of the new compound 1 was determined by means of spectral data analysis and also comparing that of reference sample of palmitine.

  4. Alkaloids from Pandanus amaryllifolius: Isolation and Their Plausible Biosynthetic Formation.

    Science.gov (United States)

    Tsai, Yu-Chi; Yu, Meng-Lun; El-Shazly, Mohamed; Beerhues, Ludger; Cheng, Yuan-Bin; Chen, Lei-Chin; Hwang, Tsong-Long; Chen, Hui-Fen; Chung, Yu-Ming; Hou, Ming-Feng; Wu, Yang-Chang; Chang, Fang-Rong

    2015-10-23

    Pandanus amaryllifolius Roxb. (Pandanaceae) is used as a flavor and in folk medicine in Southeast Asia. The ethanolic crude extract of the aerial parts of P. amaryllifolius exhibited antioxidant, antibiofilm, and anti-inflammatory activities in previous studies. In the current investigation, the purification of the ethanolic extract yielded nine new compounds, including N-acetylnorpandamarilactonines A (1) and B (2); pandalizines A (3) and B (4); pandanmenyamine (5); pandamarilactones 2 (6) and 3 (7), and 5(E)-pandamarilactonine-32 (8); and pandalactonine (9). The isolated alkaloids, with either a γ-alkylidene-α,β-unsaturated-γ-lactone or γ-alkylidene-α,β-unsaturated-γ-lactam system, can be classified into five skeletons including norpandamarilactonine, indolizinone, pandanamine, pandamarilactone, and pandamarilactonine. A plausible biosynthetic route toward 1-5, 7, and 9 is proposed.

  5. Alkaloids from an algicolous strain of Talaromyces sp.

    Science.gov (United States)

    Yang, Haibin; Li, Fang; Ji, Naiyun

    2016-03-01

    Compounds isolated and identified in a culture of the alga-endophytic fungus Talaromyces sp. cf-16 included two naturally occurring alkaloids, 2-[( S)-hydroxy(phenyl)methyl]-3-methylquinazolin-4(3H)-one ( 1a) and 2-[( R)-hydroxy(phenyl)methyl]-3-methylquinazolin-4(3H)-one ( 1b), that were identified for the first time. In addition, seven known compounds ( 2- 8) were obtained from the culture. Following chiral column chromatography, compounds 1a and 1b were identified as enantiomers by spectroscopic analyses and quantum chemical calculations. Bioassay results showed that 5 was more toxic to brine shrimp than the other compounds, and that 3- 6 could inhibit Staphylococcus aureus.

  6. Indolosesquiterpene alkaloids from the Cameroonian medicinal plant Polyalthia oliveri (Annonaceae).

    Science.gov (United States)

    Kouam, Simeon Fogue; Ngouonpe, Alain Wembe; Lamshöft, Marc; Talontsi, Ferdinand Mouafo; Bauer, Jonathan O; Strohmann, Carsten; Ngadjui, Bonaventure Tchaleu; Laatsch, Hartmut; Spiteller, Michael

    2014-09-01

    The stem bark of Polyalthia oliveri was screened for its chemical constituents using liquid chromatography high resolution mass spectrometry resulting in the isolation of three indolosesquiterpene alkaloids named 8α-polyveolinone (1), N-acetyl-8α-polyveolinone (2) and N-acetyl-polyveoline (3), together with three known compounds, dehydro-O-methylisopiline (4), N-methylurabaine (5) and polycarpol (6). The structures of the compounds were elucidated by means of high resolution mass spectrometry and different NMR techniques and chemical transformations. Their absolute configurations were assigned by ab-initio calculation of CD and ORD data (for 2 and 3) and X-ray diffraction analysis (for 2). Compounds 2 and 3 exhibited moderate antiplasmodial activity against erythrocytic stages of chloroquine-sensitive Plasmodium falciparum NF54 strain and low cytotoxicity on rat skeletal myoblast (L6) cell line.

  7. Indole alkaloid and other constituents from Ocotea minarum

    Energy Technology Data Exchange (ETDEWEB)

    Garcez, Walmir S.; Garcez, Fernanda R.; Silva, Lillian May G.E. da; Shimabukuro, Angela A. [Mato Grosso do Sul Univ., Campo Grande, MS (Brazil). Dept. de Quimica]. E-mail: wgarcez@nin.ufms.br

    2005-11-15

    From the fruits of Ocotea minarum a new ie alkaloid, tryptophol-5-O-{beta}-D-glucopyranoside, was isolated in addition to the coumarin scopoletin and the flavonoids taxifolin, quercetin-7-O-{beta}-D-glucopyranoside, eriodictyol-3'-O-{beta}-D-glucopyranoside and naringenin-7-O-{beta}-D-glucopyranoside. A new alkyl phenol, 3-(1,4-dihydroxypentyl)-5-methoxyphenol, was obtained from the heartwood in addition to 5-propylresorcinol, trans-asarone, lyonyresinol, 3-O-{beta}-D-glucopyranosyl stigmasterol and stigmasta-4,22-dien-3-one, whereas from the trunk bark the sesquiterpene lanceolic acid (as its methyl ester derivative after methylation procedures) and {beta}-sitosterol were isolated. 5-propylresorcinol and lanceolic acid are reported for the first time as natural products. (author)

  8. New vobasinyl-ibogan type bisindole alkaloids from Tabernaemontana corymbosa.

    Science.gov (United States)

    Zhang, Yu; Guo, Lingli; Yang, Guangmei; Guo, Feng; Di, Yingtong; Li, Shunlin; Chen, Duozhi; Hao, Xiaojiang

    2015-01-01

    Ten vobasinyl-ibogan type bisindole alkaloids, including three new ones, tabercorines A-C (1-3), and a new natural product, 17-acetyl-tabernaecorymbosine A (4), were isolated from the twigs and leaves of Tabernaemontana corymbosa. Their structures were elucidated on the basis of spectroscopic data, and the NMR data of 17-acetyl-tabernaecorymbosine A (4) was assigned and reported for the first time. The absolute configurations of 1-4 were determined by CD exciton chirality method. All new compounds were evaluated for in vitro cytotoxicity against various human cancer cell lines. Compounds 1 and 4 showed significant inhibitory effects with IC50 values comparable to those of cisplatin. PMID:25449423

  9. Cytochrome P450 as dimerization catalyst in diketopiperazine alkaloid biosynthesis.

    Science.gov (United States)

    Saruwatari, Takayoshi; Yagishita, Fumitoshi; Mino, Takashi; Noguchi, Hiroshi; Hotta, Kinya; Watanabe, Kenji

    2014-03-21

    As dimeric natural products frequently exhibit useful biological activities, identifying and understanding their mechanisms of dimerization is of great interest. One such compound is (−)-ditryptophenaline, isolated from Aspergillus flavus, which inhibits substance P receptor for potential analgesic and anti-inflammatory activity. Through targeted gene knockout in A. flavus and heterologous yeast gene expression, we determined for the first time the gene cluster and pathway for the biosynthesis of a dimeric diketopiperazine alkaloid. We also determined that a single cytochrome P450, DtpC, is responsible not only for pyrroloindole ring formation but also for concurrent dimerization of N-methylphenylalanyltryptophanyl diketopiperazine monomers into a homodimeric product. Furthermore, DtpC exhibits relaxed substrate specificity, allowing the formation of two new dimeric compounds from a non-native monomeric precursor, brevianamide F. A radical-mediated mechanism of dimerization is proposed.

  10. Synthesis of some /sup 11/C-labelled alkaloids

    Energy Technology Data Exchange (ETDEWEB)

    Laangstroem, B.; Antoni, G.; Halldin, H.; Svaerd, H.; Bergson, G. (Univ. of Uppsala (Sweden) Inst. of Chemistry)

    1982-01-01

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

  11. Studies of Genetic Variation of Essential Oil and Alkaloid Content in Boldo (Peumus boldus).

    Science.gov (United States)

    Vogel, H; Razmilic, I; Muñoz, M; Doll, U; Martin, J S

    1999-02-01

    Boldo is a tree or shrub with medicinal properties native to Chile. The leaves contain alkaloids and essential oils. Variation of total alkaloid concentration, of the alkaloid boldine, and essential oil components were studied in different populations from northern, central, and southern parts of its geographic range and in their progenies (half-sib families). Total alkaloid concentration showed genetic variation between progenies of the central population but not between populations. Boldine content found in concentrations of 0.007 to 0.009% did not differ significantly between populations. Principal components of the essential oil were determined genetically, with highest values for ascaridole in the population of the north and for P-cymene in the south. Between half-sib families genetic variation was found in the central and northern populations for these components. The high heritability coefficients found indicate considerable potential for successful selection of individuals for these characters. PMID:17260243

  12. 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 ...

  13. Studies on the Synthesis of Morphinan Alkaloid: Preparation of the Key Allylic Silyl Ether Precursor

    Institute of Scientific and Technical Information of China (English)

    Zhen Lei SONG; Yong Qiang TU; Shuan Hu GAO; Yi Jun JIANG; Shu Yu ZHANG

    2005-01-01

    A convergent strategy to the key allylic silyl ether precursor 4 in our synthetic efforts toward morphinan alkaloid is presented. The vital step is the selective 1,2-addition of the organocerium agent of 6 to ketene 5.

  14. Survey of Iranian Plants For Saponins Alkaloids Flavonoids And Tannins. IV

    OpenAIRE

    M.H. Salehi Surmaghi; Y. Aynehchi GH. Amin; Z. Mahmoodi

    1992-01-01

    A total of 149 plant extracts representing 49 different families has been screened for saponins, flavonoids, tannins and alkalodids. positive tests obtained were 145 (97) for saponins 74 (50%) for alkaloids 16 (51%) for fiavonoisds and 60 (40%) for tannins.

  15. RNA targeting by small molecules: Binding of protoberberine, benzophenanthridine and aristolochia alkaloids to various RNA structures

    Indian Academy of Sciences (India)

    Gopinatha Suresh Kumar

    2012-07-01

    Studies on RNA targeting by small molecules to specifically control certain cellular functions is an area of remarkable current interest. For this purpose, a basic understanding of the molecular aspects of the interaction of small molecules with various RNA structures is essential. Alkaloids are a group of natural products with potential therapeutic utility, and very recently, their interaction with many RNA structures have been reported. Especially noteworthy are the protoberberines and aristolochia alkaloids distributed widely in many botanical families. Many of the alkaloids of these group exhibit excellent binding affinity to many RNA structures that may be exploited to develop RNA targeted therapeutics. This review attempts to present the current status on the understanding of the interaction of these alkaloids with various RNA structures, mainly highlighting the biophysical aspects.

  16. Apparent effects of glyphosate on alkaloid production in coca plants grown in Colombia.

    Science.gov (United States)

    Casale, John; Lydon, John

    2007-05-01

    During the routine analysis of coca leaf material from South America, alkaloids in Erythroxylum coca var. ipadu (ECVI) leaf samples from fields suspected of being treated with glyphosate were compared with those from non-treated E. coca var. ipadu and Erythroxylum novogranatense var. novogranatense (ENVN) plants. Cocaine levels in leaf tissue from non-treated ECVI and ENVN were 0.53+/-0.08% and 0.64+/-0.08% (w/w), respectively, whereas leaves from treated plants were nearly devoid of cocaine. Further analysis demonstrated the presence of several previously undescribed N-nortropane alkaloids, several of which were tentatively identified. The results suggest that applications of glyphosate to coca plants can have dramatic effects on the quantity and quality of alkaloids produced by surviving or subsequent leaves. The analytical data presented will be of value to forensic chemists who encounter illicit cocaine preparations containing alkaloids produced from coca plants treated with glyphosate.

  17. Effect of purine alkaloids on the proliferation of lettuce cells derived from protoplasts.

    Science.gov (United States)

    Sasamoto, Hamako; Fujii, Yoshiharu; Ashihara, Hiroshi

    2015-05-01

    To investigate the ecological role of caffeine, theobromine, theophylline and paraxanthine, which are released from purine alkaloid forming plants, the effects of these purine alkaloids on the division and colony formation of lettuce cells were assessed at concentrations up to 1 mM. Five days after treatment with 500 μM caffeine, theophylline and paraxanthine, division of isolated protoplasts was significantly inhibited. Thirteen days treatment with > 250 μM caffeine had a marked inhibitory effect on the colony formation of cells derived from the protoplasts. Other purine alkaloids also acted as inhibitors. The order of the inhibition was caffeine > theophylline > paraxanthine > theobromine. These observations suggest that a relatively low concentration of caffeine is toxic for proliferation of plant cells. In contrast, theobromine is a weak inhibitor of proliferation. Possible allelopathic roles of purine alkaloids in natural ecosystems are discussed.

  18. A Journey Under the Sea: The Quest for Marine Anti-Cancer Alkaloids

    Directory of Open Access Journals (Sweden)

    Nadine Darwiche

    2011-11-01

    Full Text Available The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many are now being tested in various phases of clinical trials. Recently, marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities including anti-angiogenic, anti-proliferative, inhibition of topoisomerase activities and tubulin polymerization, and induction of apoptosis and cytotoxicity. Two tunicate-derived alkaloids, aplidin and trabectedin, offer promising drug profiles, and are currently in phase II clinical trials against several solid and hematologic tumors. This review sheds light on the rich array of anti-cancer alkaloids in the marine ecosystem and introduces the most investigated compounds and their mechanisms of action.

  19. A journey under the sea: the quest for marine anti-cancer alkaloids.

    Science.gov (United States)

    Tohme, Rita; Darwiche, Nadine; Gali-Muhtasib, Hala

    2011-01-01

    The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many are now being tested in various phases of clinical trials. Recently, marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities including anti-angiogenic, anti-proliferative, inhibition of topoisomerase activities and tubulin polymerization, and induction of apoptosis and cytotoxicity. Two tunicate-derived alkaloids, aplidin and trabectedin, offer promising drug profiles, and are currently in phase II clinical trials against several solid and hematologic tumors. This review sheds light on the rich array of anti-cancer alkaloids in the marine ecosystem and introduces the most investigated compounds and their mechanisms of action. PMID:22113577

  20. Significant differences in alkaloid content of Coptis chinensis (Huanglian, from its related American species

    Directory of Open Access Journals (Sweden)

    Skeels Matthew

    2009-08-01

    Full Text Available Abstract Background The growing popularity of Chinese herbal medicine in the United States has prompted large-scale import of raw herbs from Asia. Many of the Asian herbs have phylogenetically related North American species. We compared three phylogenetically related species, namely Coptis chinensis (Huanglian, Hydrastis canadensis and Coptis trifolia to show whether they can be substituted by one another in terms of alkaloid content. Methods We used microwave assisted extraction to obtain alkaloids berberine, coptisine, palmatine and hydrastine. High performance liquid chromatography (HPLC was used to quantify each alkaloid. Results Hydrastis canadensis has the most berberine, whereas Coptis trifolia has the most coptisine. Hydrastine and palmatine were unique to Hydrastis canadensis and Coptis chinensis respectively. Conclusion Neither Hydrastis canadensis nor Coptis trifolia contains all the alkaloids found in Coptis chinensis used in Chinese medicine. Substitutes of this Chinese species by its American relatives are not recommended.

  1. 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......, anhydrolycodoline, gnidioidine, lycofoline, lannotinidine D, and acrifoline, as well as a previously unknown N-oxide of annotine. (1)H and (13)C NMR data of several of the alkaloids were provided for the first time. Solvent-dependent equilibrium constants between ketone and hemiketal form of acrifoline were...... determined. Conformation of acrifoline was characterized using NOESY spectroscopy and molecular modelling. The isolated alkaloids were evaluated for their in vitro inhibitory activity against acetylcholinesterase and butyrylcholinesterase. Ligand docking studies based on mutated 3D structure of Torpedo...

  2. Using Natural Cinchona Alkaloids to Promote the Enantioselective Addition of Dialkylzinc to N-Diphenylphosphinylimines

    Institute of Scientific and Technical Information of China (English)

    张海乐; 方春梅; 李昕; 龚流柱; 宓爱巧; 崔欣; 蒋耀忠

    2003-01-01

    Cinchona alkaloids are utilized as chiral ligands to promote the enantioselective addition of dialkylzinc to N-diphenyiphosphinylirnlnes affording enantiomerically enriched N-diphenyiphosphinylamines in up to 91% ee.

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

    Directory of Open Access Journals (Sweden)

    Sérgio Freire de Carvalhaes

    2002-01-01

    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.

  4. Poor alkaloid sequestration by arrow poison frogs of the genus Phyllobates from Costa Rica.

    Science.gov (United States)

    Mebs, Dietrich; Alvarez, Joseph Vargas; Pogoda, Werner; Toennes, Stefan W; Köhler, Gunther

    2014-03-01

    Frogs of the genus Phyllobates from Colombia are known to contain the highly toxic alkaloid batrachotoxin, but species from Central America exhibit only very low levels or are entirely free of this toxin. In the present study alcohol extracts from 101 specimens of Phyllobates lugubris and Phyllobates vittatus and 21 of three sympatric species (Dendrobates pumilio, Dendrobates auratus, Dendrobates granuliferus) from Costa Rica were analyzed by gas chromatography-mass spectrometry. Whereas the extracts of the Dendrobates species exhibited typical profiles of toxic alkaloids, those of the two Phyllobates species contained low levels of few alkaloids only, batrachotoxin was not detected. Although the feeding pattern of the Dendrobates and Phyllobates species are similar as revealed by examination of their stomach content (mainly ants and mites), the Phyllobates species are poorly sequestering alkaloids from their food source in contrast to the Dendrobates frogs. PMID:24467995

  5. ISOLATION AND PURIFICATION OF ALKALOIDS FROM PLUMULA NELUMBINIS BY DOUBLE-COLUMN ADSORPTION CHROMOTOGRAPHY

    Institute of Scientific and Technical Information of China (English)

    ZHANG Jixiang; GUO Jinsheng; OU Lailiang

    2007-01-01

    The performance of adsorption and separation for liensinine, isoliensinine and neferine was studied by double-column adsorption chromatography using macroporous adsorption and cation exchange resins. The alkaloid extract with 49.2% total contents by mass representing 10.6% liensinine, 10.6% isoliensinine and 28.0% neferine respectively was prepared by D72 cation exchange resins, in which most of the impurities were water-soluble alkaloids. Furthermore, the alkaloid extract with 82.6% total contents by mass containing 33.1%, 15.0% and 34.5% of the three adsorbates respectively was prepared by double-column adsorption chromatography using AKS-W macroporous adsorption and D72 cation exchange resins. As a result, the content of single and total alkaloids has been greatly increased by the double-column adsorption chromatography.

  6. ISOLATION AND PURIFICATION OF ALKALOIDS FROM PLUMULA NELUMBINIS BY DOUBLE-COLUMN ADSORPTION CHROMOTOGRAPHY

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    The performance of adsorption and separation for liensinine, isoliensinine and neferine was studied by double-column adsorption chromatography using macroporous adsorption and cation exchange resins. The alkaloid extract with 49.2% total contents by mass representing 10.6% liensinine, 10.6% isoliensinine and 28.0% neferine respectively was prepared by D72 cation exchange resins, in which most of the impurities were water-soluble alkaloids. Furthermore,the alkaloid extract with 82.6% total contents by mass containing 33.1%, 15.0% and 34.5% of the three adsorbates respectively was prepared by double-column adsorption chromatography using AKS-W macroporous adsorption and D72 cation exchange resins. As a result, the content of single and total alkaloids has been greatly increased by the double-column adsorption chromatography.

  7. 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.

  8. Lucidimine A-D, four new alkaloids from the fruiting bodies of Ganoderma lucidum.

    Science.gov (United States)

    Zhao, Zhen-Zhu; Chen, He-Ping; Feng, Tao; Li, Zheng-Hui; Dong, Ze-Jun; Liu, Ji-Kai

    2015-01-01

    Four new polycylic alkaloids, lucidimine A-D, were isolated from the fruiting bodies of Ganoderma lucidum. Their chemical structures were established based on 1D and 2D NMR data as well as HREIMS/HRESIMS analyses. PMID:26666338

  9. Three new C19-diterpenoid alkaloids from Delphinium laxicymosum var. Pilostachyum

    Institute of Scientific and Technical Information of China (English)

    Ping Tang; Dong Lin Chen; Qiao Hong Chen; Xi Xian Jian; Feng Peng Wang

    2007-01-01

    Three new lycoctonine-type C19-diterpenoid alkaloids, laxicymine 1, laxicymisine 2, and laxicyminine 3 have been isolated from the whole herb of Delphinium laxicymosum var.pilostachyum W.T.Wang.Their structures were established by spectra data.

  10. In vitro androgenetic cultures of Hyoscyamus niger L., H. albus L. and alkaloid content assay

    Directory of Open Access Journals (Sweden)

    Maria Wesołwska

    2014-02-01

    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.

  11. Molecular geometry of alkaloids present in seeds of mexican prickly poppy

    OpenAIRE

    Gobato, Ricardo; Fedrigo, Desire Francine Gobato; Gobato, Alekssander

    2015-01-01

    The work is a study of the geometry of the molecules via molecular mechanics of the main alkaloids found in the seeds of Argemone Mexicana Linn, a prickly poppy, which is considered one of the most important species of plants in traditional Mexican and Indian medicine system. The seeds have toxic properties as well as bactericide, hallucinogenic, fungicide, insecticide, in isoquinolines and sanguinarine alkaloids such as berberine. A computational study of the molecular geometry of the molecu...

  12. Antibacterial activity of the alkaloid extract and isolated compounds from Croton bonplandianum Baill. (Euphorbiaceae)

    OpenAIRE

    Burgos, A.; J. BARUA; M.E. FLORES-GIUBI; D. BAZAN; Ferro, E.; N.L. ALVARENGA

    2015-01-01

    ABSTRACT The antibacterial activity of the alkaloid extract from the leaves of Croton bonplandianum Baill. and its main compounds, sparsiflorine and crotsparine, was tested against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa by the resazurin microtitre-plate method. Pure compounds were identified by spectroscopic techniques, mainly 1D and 2D NMR. The alkaloid extract showed activity particularly against the S. aureus and P. aeruginosa. Regarding t...

  13. 6-O-Methylkrigeine, a new amaryllidaceae alkaloid from Nerine huttoniae Schönland

    DEFF Research Database (Denmark)

    Molander, Marianne; Christensen, Søren Brøgger; Jäger, Anna Katharina;

    2012-01-01

    A novel Amaryllidaceae alkaloid, 6-O-methylkrigeine has been isolated from Nerine huttoniae and the configuration elucidated by 1D and 2D 1H NMR, 13C NMR, HRMS and optical rotation.......A novel Amaryllidaceae alkaloid, 6-O-methylkrigeine has been isolated from Nerine huttoniae and the configuration elucidated by 1D and 2D 1H NMR, 13C NMR, HRMS and optical rotation....

  14. A novel alkaloid from the fruiting bodies of Ganoderma sinense Zhao,Xu et Zhang

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    A new alkaloid,sinensine(1),had been isolated from the fruiting bodies of Ganoderma sinense Zhao,Xu et Zhang.Its structure was elucidated on the basis of 1D and 2D spectral analysis.This alkaloid exhibited activity in protecting the injury induced by hydrogen peroxide oxidation on HUVEC,with EC_(50) value 6.2μmol/L.

  15. Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters

    Directory of Open Access Journals (Sweden)

    Wen-Bin Yi

    2012-08-01

    Full Text Available A fluorous cinchona alkaloid ester has been developed as a chiral promoter for the asymmetric fluorination of β-ketoesters. It has comparable reactivity and selectivity to the nonfluorous versions of cinchona alkaloids and can be easily recovered from the reaction mixture by simple fluorous solid-phase extraction (F-SPE and used for the next round of reaction without further purification.

  16. Naphthylisoquinoline Alkaloids : Structural Elucidation, Metabolism and Functional Analysis of their Bioactivities

    OpenAIRE

    Faber, Johan Henrik

    2007-01-01

    This thesis deals with the isolation and structural elucidation of bioactive naphthylisoquinoline alkaloids and related analogs. The mode of action of the antiplasmodial activity exhibited by the naphthylisoquinoline alkaloids was explored and compared to that of the antimalarial drug chloroquine. Furthermore, the phase 1 and 2 metabolism of dioncophyllines A and C and dioncopeltine A were investigated. In detail the following results have been obtained: • From the leaves of the recently disc...

  17. HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus

    OpenAIRE

    Sawaya, Alexandra; Abreu, Ilka Nacif; Andreazza, Nathalia Luiza; Marcos N Eberlin; Mazzafera, Paulo

    2008-01-01

    Pilocarpine, an important imidazole alkaloid, is extracted from the leaves of Pilocarpus microphyllus (Rutaceae), known in Brazil as jaborandi and used mainly for the treatment of glaucoma. Jaborandi leaves also contain other imidazole alkaloids, whose pharmacological and physiological properties are unknown, and whose biosynthetic pathways are under investigation. In the present study, a HPLC method coupled with ESI-MSn was developed for their qualitative and quantitative analysis. This meth...

  18. Isolation and X-ray Crystal Structure of Tetrahydroisoquinoline Alkaloids from Calycotome Villosa Subsp. intermedias

    Directory of Open Access Journals (Sweden)

    Mohammed Lachkar

    2004-07-01

    Full Text Available Two tetrahydroisoquinoline alkaloids were extracted from the alkaloid fraction of a methanol extract of the seeds of Calycotome Villosa Subsp. intermedia. Their structures were established as (R-1-hydroxymethyl-7-8-dimethoxy-1,2,3,4-tetrahydro- isoquinoline (1 and (S-7-hydroxymethyl-2-3-dimethoxy-7,8,9,10-tetrahydroisoquinoline chloride (2 by spectroscopic techniques and X-ray diffraction analysis.

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

    OpenAIRE

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

    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...

  20. Isolation and Characterization of Antineoplastic Alkaloids from Catharanthus Roseus L. Don. Cultivated in Egypt

    OpenAIRE

    Shams, Khaled A; Nazif, Naglaa M; Abdel Azim, Nahla S; Abdel Shafeek, Khaled A; El-Missiry, Mostafa M.; Ismail, Shams I; Seif El Nasr, Medhat M

    2009-01-01

    Vinblastine and vincristine (the antileukemic agents) were isolated, in a pure form, from Catharanthus roseus L. Don., cultivated in Egypt, by several chromatographic techniques. Five modified methods for the preparation of total alkaloids were carried out. All the isolated mixtures were evaluated by HPLC and HPTLC analyses. The antineoplastic alkaloids; vinblastine and vincristine, were isolated by the use of vacuum liquid chromatographic column on silica gel : aluminium oxide (1:1) mixed be...

  1. Unlocking the Diversity of Alkaloids in Catharanthus roseus: Nuclear Localization Suggests Metabolic Channeling in Secondary Metabolism

    OpenAIRE

    Stavrinides, Anna; Tatsis, Evangelos C.; Foureau, Emilien; Caputi, Lorenzo; Kellner, Franziska; Courdavault, Vincent; O’Connor, Sarah E.

    2015-01-01

    Summary The extraordinary chemical diversity of the plant-derived monoterpene indole alkaloids, which include vinblastine, quinine, and strychnine, originates from a single biosynthetic intermediate, strictosidine aglycone. Here we report for the first time the cloning of a biosynthetic gene and characterization of the corresponding enzyme that acts at this crucial branchpoint. This enzyme, an alcohol dehydrogenase homolog, converts strictosidine aglycone to the heteroyohimbine-type alkaloid ...

  2. A Stereoselective Hydroxylation Step of Alkaloid Biosynthesis by a Unique Cytochrome P450 in Catharanthus roseus*

    OpenAIRE

    Giddings, Lesley-Ann; Liscombe, David K.; Hamilton, John P; Childs, Kevin L.; DellaPenna, Dean; Buell, C. Robin; O'Connor, Sarah E.

    2011-01-01

    Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes they encode remain unknown. Here, we report the identification and functional characterization of a cytochrome P450 gene in a new subfamily of CYP71, CYP71BJ1, involved in alkaloid biosynthesis. Co-expression analysis ...

  3. Effect of Drying Methods on the Steroidal Alkaloid Content of Potato Peels, Shoots and Berries

    OpenAIRE

    Hossain, Mohammad B.; Nigel P. Brunton; Rai, Dilip K.

    2016-01-01

    The present study has found that dried potato samples yielded significantly higher levels of steroidal alkaloids such as α-solanine and α-chaconine than the corresponding fresh samples, as determined by the UPLC-MS/MS technique. Among the drying techniques used, air drying had the highest effect on steroidal alkaloid contents, followed by freeze drying and vacuum oven drying. There was no significant difference between the freeze dried and vacuum oven dried samples in their α-chaconine conten...

  4. Annonamine, a new aporphine alkaloid from the leaves of Annona muricata.

    Science.gov (United States)

    Matsushige, Ayano; Kotake, Yaichiro; Matsunami, Katsuyoshi; Otsuka, Hideaki; Ohta, Shigeru; Takeda, Yoshio

    2012-01-01

    Atypical Parkinsonism in the Caribbean Island Guadeloupe is thought to be associated with the consumption of plants of the Annonaceae family, especially Annona muricata (soursop). In this study, a new aporphine alkaloid named annonamine (1) was isolated from the leaves of A. muricata L. together with four known benzylisoquinoline alkaloids (2-5). The structures of the isolated compounds were elucidated by the spectroscopic method.

  5. Alkaloids of Cynanchum vincetoxicum: Efficacy against MDA-MB-231 Mammary Carcinoma Cells

    OpenAIRE

    Tanner, U.; Wiegrebe, Wolfgang

    1993-01-01

    Alkaloids 1-4 from Cynanchum vincetoxicum (asclepiadaceae) (Scheme 1) do not have affinity to the oestrogen receptor but they inhibit the growth of the hormone-independent mammary carcinoma cells MDA-MB-231 (Fig. 1) and bind to nucleosides and nucleotides (Table 1). Intercalation was not observed. Die Alkaloide 1-4 aus Cynanchum vincetoxicum (Asclepiadaceae) (Scheme 1) zeigen keine Affinität zum Oestrogen-Rezeptor, hemmen aber das Wachstum der hormonunabhängigen Mammakar...

  6. 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. PMID:25496282

  7. Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax.

    Science.gov (United States)

    Pesqueira, A; Harmon, D L; Branco, A F; Klotz, J L

    2014-03-01

    The ergot alkaloid ergovaline has demonstrated a persistent and sustained contractile response in several different vascular models. It was hypothesized that different alkaloids isolated from tall fescue (Lolium arundinaceum) will contribute to this contractile response differently. The objective was to compare contractile-response patterns of single additions of the ergoline alkaloids lysergic acid, lysergol, and ergonovine and the ergopeptine alkaloids ergotamine, ergocristine, ergocryptine, ergocornine, and ergovaline (provided as tall fescue seed extract). Lateral saphenous veins were collected from 6 Holstein steers (BW = 397 ± 28 kg) immediately after slaughter, sliced into cross-sections, and suspended in myograph chambers containing oxygenated Krebs-Henseleit buffer (95% O2/5% CO2; pH = 7.4; 37°C). Treatments were added at 0 min and buffer was replaced in 15-min intervals for a 120-min incubation. In addition to maximum tension and time to reach maximum tension, percent relaxation and rate of relaxation were determined following maximum tension for each treatment. All compounds tested produced significant contractile responses (P ergotamine, ergocristine, ergocryptine, and ergocornine had slower developing contractile responses with a longer (P < 0.05) interval until maximum tension was achieved compared to the ergoline alkaloids. Maximal responses to all the ergopeptine alkaloids, however, all persisted for the 120-min duration with negligible relaxation occurring. The different classes of alkaloids differed greatly in the type of contractile response generated in the lateral saphenous vein. Persistence of contractile response is thought to be the primary contributing factor to the vasoconstriction observed in animals demonstrating signs of fescue toxicosis, where different ergot alkaloids can contribute differently. PMID:24492541

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

    International Nuclear Information System (INIS)

    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, 1H-NMR and MS). The isolated compound showed significant antibacterial activity against Streptococcus pyogenus.

  9. Recognition of chromatin by the plant alkaloid, ellipticine as a dual binder

    International Nuclear Information System (INIS)

    Recognition of core histone components of chromatin along with chromosomal DNA by a class of small molecule modulators is worth examining to evaluate their intracellular mode of action. A plant alkaloid ellipticine (ELP) which is a putative anticancer agent has so far been reported to function via DNA intercalation, association with topoisomerase II and binding to telomere region. However, its effect upon the potential intracellular target, chromatin is hitherto unreported. Here we have characterized the biomolecular recognition between ELP and different hierarchical levels of chromatin. The significant result is that in addition to DNA, it binds to core histone(s) and can be categorized as a ‘dual binder’. As a sequel to binding with histone(s) and core octamer, it alters post-translational histone acetylation marks. We have further demonstrated that it has the potential to modulate gene expression thereby regulating several key biological processes such as nuclear organization, transcription, translation and histone modifications. - Highlights: • Ellipticine acts a dual binder binding to both DNA and core histone(s). • It induces structural perturbations in chromatin, chromatosome and histone octamer. • It alters histones acetylation and affects global gene expression

  10. Acridone Alkaloids from Swinglea glutinosa (Rutaceae) and Their Effects on Photosynthesis.

    Science.gov (United States)

    Arato Ferreira, Pedro H; Dos Santos, Djalma A P; da Silva, Maria Fátima das G F; Vieira, Paulo C; King-Diaz, Beatriz; Lotina-Hennsen, Blas; Veiga, Thiago A M

    2016-01-01

    Continuing our search for herbicide models based on natural products, we investigated the action mechanisms of five alkaloids isolated from Swinglea glutinosa (Rutaceae): Citrusinine-I (1), glycocitrine-IV (2), 1,3,5-trihydroxy-10-methyl- 2,8-bis(3-methylbut-2-en-1-yl)-9(10H)-acridinone (3), (2R)-2-tert-butyl-3,10-dihydro-4,9-dihydroxy-11-methoxy-10-methylfuro[3,2-b]acridin-5(2H)-one (4), and (3R)-2,3,4,7-tetrahydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-12H-pyrano[2,3-a]acridin-12-one (5) on several photosynthetic activities in an attempt to find new compounds that affect photosynthesis. Through polarographic techniques, the compounds inhibited the non-cyclic electron transport in the basal, phosphorylating, and uncoupled conditions from H2 O to methylviologen (=MV). Therefore, they act as Hill reaction inhibitors. This approach still suggested that the compounds 4 and 5 had their interaction site located at photosystem I. Studies on fluorescence of chlorophyll a suggested that acridones (1-3) have different modes of interaction and inhibition sites on the photosystem II electron transport chain. PMID:26765357

  11. Antinociceptive and Anti-Inflammatory Effects of Total Alkaloid Extract from Fumaria capreolata

    Directory of Open Access Journals (Sweden)

    Noureddine Bribi

    2015-01-01

    Full Text Available Fumaria capreolata is used in traditional medicine in North Africa for its gastrointestinal and anti-inflammatory activities. The present study investigates the effects of total alkaloids extracted from the aerial parts of Fumaria capreolata (AFC on LPS-induced production of proinflammatory mediators (IL-6, IL-1β, iNOS, TNF-α, COX-2, and MIP-2 in RAW264.7 cells. AFC significantly reduced the inflammatory response inhibiting the production of nitric oxide (NO and IL-6 in a dose-dependent manner, without affecting the viability of cells, and downregulated mRNA expression of proinflammatory key players: IL-6, IL-1β, iNOS, TNF-α, and COX-2. AFC antinociceptive and anti-inflammatory properties were also evaluated on the acetic acid- and formalin-induced pain models in mice. AFC oral administration significantly inhibited acetic acid-induced writhes and reduced formalin-induced paw licking time. Therefore, AFC may be a potential candidate for the treatment of inflammatory diseases, such as colitis and arthritis.

  12. Recognition of chromatin by the plant alkaloid, ellipticine as a dual binder

    Energy Technology Data Exchange (ETDEWEB)

    Banerjee, Amrita; Sanyal, Sulagna; Majumder, Parijat [Biophysics & Structural Genomics Division, Saha Institute of Nuclear Physics, Block-AF, Sector-1, Bidhan Nagar, Kolkata 700064, West Bengal (India); Chakraborty, Payal [Bionivid Technology Pvt Ltd, Kasturi Nagar, Bangalore 560043 (India); Jana, Kuladip [Division of Molecular Medicine, Centre for Translational Animal Research, Bose Institute, P-1/12 C.I.T. Scheme VIIM, Kolkata 700054, West Bengal (India); Das, Chandrima, E-mail: chandrima.das@saha.ac.in [Biophysics & Structural Genomics Division, Saha Institute of Nuclear Physics, Block-AF, Sector-1, Bidhan Nagar, Kolkata 700064, West Bengal (India); Dasgupta, Dipak, E-mail: dipak.dasgupta@saha.ac.in [Biophysics & Structural Genomics Division, Saha Institute of Nuclear Physics, Block-AF, Sector-1, Bidhan Nagar, Kolkata 700064, West Bengal (India)

    2015-07-10

    Recognition of core histone components of chromatin along with chromosomal DNA by a class of small molecule modulators is worth examining to evaluate their intracellular mode of action. A plant alkaloid ellipticine (ELP) which is a putative anticancer agent has so far been reported to function via DNA intercalation, association with topoisomerase II and binding to telomere region. However, its effect upon the potential intracellular target, chromatin is hitherto unreported. Here we have characterized the biomolecular recognition between ELP and different hierarchical levels of chromatin. The significant result is that in addition to DNA, it binds to core histone(s) and can be categorized as a ‘dual binder’. As a sequel to binding with histone(s) and core octamer, it alters post-translational histone acetylation marks. We have further demonstrated that it has the potential to modulate gene expression thereby regulating several key biological processes such as nuclear organization, transcription, translation and histone modifications. - Highlights: • Ellipticine acts a dual binder binding to both DNA and core histone(s). • It induces structural perturbations in chromatin, chromatosome and histone octamer. • It alters histones acetylation and affects global gene expression.

  13. Measurement of antiphotooxidative properties of isoquinoline alkaloids using transient thermal lens spectroscopy

    Science.gov (United States)

    Hung, J.; Castillo, J.; Laboren, I.; Rodríguez, M.; Hassegawa, M.

    2005-11-01

    The antiphotooxidative properties of boldine and chloride berberine were studied by time-resolved thermal lensing technique. These compounds belong to isoquinoline alkaloids possessing interesting biological activity (e.g. antibacterial, antimalarial, antitumor). Antiphotooxidative properties of the alkaloids were studied by mechanism of energy transference between powerful oxidizing agents such as singlet oxygen. Singlet oxygen was produced by energy transfer from chlorophyll-sensitized photooxidation of oil by exposure of high light intensities like laser. The lifetimes of singlet oxygen in dimethylsulfoxide, methanol and water were determined to confirm the assignment of the singlet molecular oxygen O II (1Δ g) in the experiments. In order to understand the effect of the alkaloids on active oxygen species, we carried out in detail an analysis of the thermal lensing signal. It was shown that the alkaloids can act as quenchers of singlet oxygen. To demonstrate the ability of the alkaloids to act efficient singlet oxygen acceptors, we have measured the fluorescence spectra of the studied alkaloids in the presence and in the absence of singlet oxygen. The antiphotooxidative activity of boldine and chloride berberine can be explained by the ability to quench singlet oxygen.

  14. Antibacterial properties of Alkaloid rich fractions obtained from various parts of Prosopis juliflora

    Directory of Open Access Journals (Sweden)

    Shachi Singh,

    2011-03-01

    Full Text Available The alkaloid rich fraction obtained from various parts of Prosopis juliflora were assessed for their antibacterial property using disc diffusion method on several Gram-negative and Gram-positive bacterial strains like E.coli, Staphylococcus aureus, Bacillus cereus, Psuedomonas putida, Klebsiella, Salmonella, Acinetobacter andAlcaligen. Strong antibacterial effect was shown by leaf, pod and flower extract, with MIC value ranging between 25μg/ml-100μg/ml. The extracts of leaves showed highest activity among all the plant parts. Klebsiella was found to be the most susceptible bacteria, whereas Acinetobacter and Alcaligen were the least susceptible. A comparison of zone of inhibition created by alkaloid rich fractions with that of standard antibiotics, ampicillin, tetracycline, chloramphenicol, oflaxacin, refampin, streptomycin and sulfa drug showed a comparable zone of inhibition. Growth of Acinetobacter and Alcaligen which were not inhibited by antibiotics, showed inhibition by the alkaloidal extracts, similarly a known ampicillin resistant E.coli strain was found to be inhibited by the plant extracts. Alkaloids present in the extracts were analysed by DART-MS. DART-MS analysis of the alkaloid rich fractions showed the presence of piperidine alkaloids.

  15. Inhibitory effects of alkaloids from Sophora alopecuroids on feeding,development and reproduction of Clostera anastomosis

    Institute of Scientific and Technical Information of China (English)

    Yang Zhende; Zhao Boguang; Zhu Lin; Fang Jie; Xia Luqing

    2006-01-01

    Alkaloids from Sophora alopecuroids were bioassayed with Clostera anastomosis for their antifeedant and growth inhibitory effects.The antifeedant rate in choice test reached 62%-86% at the dose 2.5 mg/mL,while in non-choice bioassay the rate was only 20%-29%.In choice bioassay,the anfifeedant rate increased with larval instars of C anastomosis and did not in non-choice experiment.The alkaloids also imposed a strong influence on the growth of C anastomosis larvae,i.e.,after feeding on the leaves treated with alkaloid,the larvae lost their weight,weight gain,and relative growth rate (RGR) significantly when compared with the controls.In the second day after treatment with the dose at 10 mg/mL of the alkaloid,the RGR reduced by 39.8%,and the food intake and the feces weight were respectively 57.7% and 57.4% of the controls.The approximate digestibility (AD) increased significantly,and the efficiency in converting digested food (ECD),and the efficiency in converting ingested food (ECI) decreased greatly after feeding the treated leaves.Moreover,the eggs laid per female were also inhibited by this alkaloid.The significance and prospect of the alkaloids in controlling forest insect pests were also discussed.

  16. A Stereoselective Hydroxylation Step of Alkaloid Biosynthesis by a Unique Cytochrome P450 in Catharanthus roseus*

    Science.gov (United States)

    Giddings, Lesley-Ann; Liscombe, David K.; Hamilton, John P.; Childs, Kevin L.; DellaPenna, Dean; Buell, C. Robin; O'Connor, Sarah E.

    2011-01-01

    Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes they encode remain unknown. Here, we report the identification and functional characterization of a cytochrome P450 gene in a new subfamily of CYP71, CYP71BJ1, involved in alkaloid biosynthesis. Co-expression analysis of putative cytochrome P450 genes in the Catharanthus roseus transcriptome identified candidate genes with expression profiles similar to known terpene indole alkaloid biosynthetic genes. Screening of these candidate genes by functional expression in Saccharomyces cerevisiae yielded a unique P450-dependent enzyme that stereoselectively hydroxylates the alkaloids tabersonine and lochnericine at the 19-position of the aspidosperma-type alkaloid scaffold. Tabersonine, which can be converted to either vindoline or 19-O-acetylhörhammericine, represents a branch point in alkaloid biosynthesis. The discovery of CYP71BJ1, which forms part of the pathway leading to 19-O-acetylhörhammericine, will help illuminate how this branch point is controlled in C. roseus. PMID:21454651

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

    Energy Technology Data Exchange (ETDEWEB)

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

    2013-05-15

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

  19. 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

    2013-06-01

    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

  20. 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)

    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 14C-Tryptamine are capable of synthesizing alkaloids. The pattern of alkaloids synthesis changes when protoplasts are subjected to a heat shock at 370C. The heat shocked protoplasts incorporated 33% more 14C-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

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

    Energy Technology Data Exchange (ETDEWEB)

    Saleem, M.; Cutler, A.J.

    1986-04-01

    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 /sup 14/C-Tryptamine are capable of synthesizing alkaloids. The pattern of alkaloids synthesis changes when protoplasts are subjected to a heat shock at 37/sup 0/C. The heat shocked protoplasts incorporated 33% more /sup 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.

  2. 小花棘豆总生物碱抑菌作用的研究%Study on Bacteriostasis Efficiency of Total Alkaloids in Oxytropis glabra DC

    Institute of Scientific and Technical Information of China (English)

    王帅; 李怀志; 马明; 张玲; 马春晖

    2012-01-01

    [目的]研究小花棘豆总生物碱的抑菌作用.[方法]通过体外抑菌试验研究小花棘豆总生物碱的抑菌活性、最小抑菌浓度(MIC)、最小杀菌浓度(MBC)和影响小花棘豆总生物碱抑菌效果的因素.[结果]小花棘豆总生物碱对金黄色葡萄球菌、乳房链球菌、化脓链球菌和枯草芽孢杆菌有抑菌作用;其对乳房链球菌和化脓链球菌的MIC为6.3 mg/mL,对金黄色葡萄球菌的MIC为1.6 mg/mL,对枯草芽孢杆菌的MIC为0.8 mg/mL.生物碱在不同pH值下的抑菌活性发生变化;高温使其抑菌活性消失;紫外照射对其稳定性没有影响.[结论]小花棘豆总生物碱对部分革兰氏阳性菌有较好的抑菌作用.%[ Objective ] The purpose of this project aim to study the antimicrobial activities of total alkaloids for Oxytropis glabra DC. [Method] Through bacteriostasis experiments in vitro, antimicrobial activities of total alkaloids for Oxytropis glabra DC on bacteriostasis efficiency, minimal inhibitory concentration, minimal bactericidal concentration, and environmental effect were studied . [Result]The result showed that alkaloid of Oxytropis glabra DC had fairly bacteriostasis for Staphylococcus aureus, Streptococcus uberis, Streptococcus pyogene, Bacillus subtilis; the MIC for Streptococcus uberis and Streptococcus pyogene was 6. 3 mg/Ml, the MIC for Staphylococcus aureus was 1. 6 mg/Ml, the MIC for Bacillus subtilis was 0. 8 mg/ Ml. The diversity of bacteriostasis efficiency of alkaloid happened in different power of hydrogen; the bacteriostasis material has bad heat stability; ultraviolet ray treatment does not affect its stability. [Conclusion] Total alkaloids of Oxytropis glabra DC had obvious bacteriostasis effect for Gram - positive bacteria.

  3. An analysis of Sorghum halepense’s behavior in presence of tropane alkaloids from Datura stramonium extracts

    OpenAIRE

    Butnariu Monica

    2012-01-01

    Abstract Background This study aimed to quantify the allelopathic potential of Datura stramonium (Jimson weed). Sorghum halepense (Johnsongrass) tolerance was assessed by germinating, seed and growing seedlings, dosing of photo-synthesis pigments, followed by treatment with D. stramonium extract tropane alkaloids. Results Preliminary chemical analysis of the extracts showed the presence of alkaloids. The presence of alkaloids was confirmed through HPLC–UV system analysis. Various concentratio...

  4. Mass spectra of alkaloids from cissampelos pareira L Mass spectra of alkaloids from cissampelos pareira L.

    Directory of Open Access Journals (Sweden)

    Aguirre Gálviz Luis Enrique

    1988-06-01

    -bidi-font-family:"Times New Roman"; mso-bidi-theme-font:minor-bidi; mso-fareast-language:EN-US;} .MsoPapDefault {mso-style-type:export-only; margin-bottom:10.0pt; line-height:115%;} @page WordSection1 {size:612.0pt 792.0pt; margin:70.85pt 3.0cm 70.85pt 3.0cm; mso-header-margin:36.0pt; mso-footer-margin:36.0pt; mso-paper-source:0;} div.WordSection1 {page:WordSection1;} -->

    The mass spectra of the tertiary bis-benzyl-isoquinoline alkaloids, warifteine and methyl-warifteine, extracted from the ethnobotanically important species, Cissampelos pareira L.. are discussed. Infonnation about the reltive positions of two hydroxyl and two methoxyl groups in warifteine and the presence of a p-xylyl moiety in both compounds in provided.

    Se presenta una discusión de los espectros de masas de warifteina y metilwarifteina, dos alcaloides

  5. Cynoglossum officinale toxicity in calves.

    Science.gov (United States)

    Baker, D C; Pfister, J A; Molyneux, R J; Kechele, P

    1991-05-01

    Six calves were given dried, ground Cynoglossum officinale daily in a dose which provided 15 (two calves) or 60 (four calves) mg per kg per day of total pyrrolizidine alkaloids. Those calves given 60 mg per kg of total pyrrolizidine alkaloids per day died following a single dose of plant material. These calves had a marked elevation of serum gamma-glutamyltransferase (GGT) and aspartate transaminase (AST) activities and serum bile acid and total bilirubin (TBili) concentrations. These four calves all had massive hepatocellular necrosis and haemorrhage of the liver. Of the two calves that were given 15 mg per kg of total pyrrolizidine alkaloids per day, one died on day 34 and the other survived until day 35 when it was painlessly killed. There were significant elevations in serum AST and GGT activities in these calves. The histological lesions of the calf surviving until 35 days were compatible with pyrrolizidine alkaloid toxicity, that is megalocytosis, karyomegaly and necrosis of hepatocytes with karyomegaly of biliary epithelium. The pyrrolizidine base present in Cynoglossum officinale (heliotridine) and its esters have a similar type of toxicity to the highly toxic and more familiar macrocyclic diester pyrrolizidine alkaloids of the pyrrolizidine base (retronecine), present in Senecio or Crotolaria species.

  6. Variación en la producción de alcaloides en inflorescencias de Senecio Grisebachii por deficiencia de nutrientes Alkaloid production changes due to nutrient deficiencies in Senecio Grisebachii inflorescences

    Directory of Open Access Journals (Sweden)

    Margarita A Yaber Grass

    2009-06-01

    Full Text Available Senecio grisebachii Baker es una maleza que invade pasturas naturales y cultivos en el sur de Brasil, Uruguay, y provincias mesopotámicas y Buenos Aires en la Argentina y es considerada tóxica debido a la presencia de alcaloides pirrolizidínicos (APs en sus tejidos. Se evaluó el efecto de la deficiencia de nitrógeno y de fósforo sobre el perfil de APs en inflorescencias de esta maleza. Se realizó un ensayo utilizando un diseño completamente aleatorizado con 10 repeticiones, en el cual las plantas, que crecieron en hidroponia desde mayo hasta octubre, fueron regadas con solución de nutrientes en las que las concentraciones de N o de P reducidas en un 50% respecto del control. La cuantificación de APs en las inflorescencias de S. grisebachii por CG y CG-EM, demuestra un aumento significativo en el contenido total de APs, en los tratamientos con déficit en N o P (1,33 y 1,34 mg g-1 de materia seca, respectivamente, comparados con el control 0,35 mg g-1. Se identificaron siete APs y sus concentraciones variaron entre tratamientos. Senecionina resultó el alcaloide mayoritario en el tratamiento déficit de N, mientras senecifilina resultó más abundante en los tratamientos control y con déficit de P, seguidos en todos los casos por integerrimina y cantidades menores de espartiodina, jacobina, jacozina y retrorsina.Senecio grisebachii Baker is a weed that invades natural pastures and crops in southern Brazil, Uruguay, the mesopotamic provinces and Buenos Aires in Argentina, and is considered to be toxic because of the presence of pyrrolizidine alkaloids (PAs in its tissues. The effects of nitrogen and phosphorus deficiency was evaluated on the APs patterns of the weed inflorescences. A completely randomized design with 10 repetitions was used in an experiment where plants growing in hydroponics from May to October were irrigated with a nutrient solution containing 50% P or N concentrations with respect to the control treatment. PAs

  7. The alkaloid gramine in the anaerobic digestion process-inhibition and adaptation of the methanogenic community.

    Science.gov (United States)

    Popp, Denny; Harms, Hauke; Sträuber, Heike

    2016-08-01

    As many plant secondary metabolites have antimicrobial activity, microorganisms of the anaerobic digestion process might be affected when plant material rich in these compounds is digested. Hitherto, the effects of plant secondary metabolites on the anaerobic digestion process are poorly investigated. In this study, the alkaloid gramine, a constituent of reed canary grass, was added daily to a continuous co-digestion of grass silage and cow manure. A transient decrease of the methane yield by 17 % and a subsequent recovery was observed, but no effect on other process parameters. When gramine was infrequently spiked in higher amounts, the observed inhibitory effect was even more pronounced including a 53 % decrease of the methane yield and an increase of acetic acid concentrations up to 96 mM. However, the process recovered and the process parameters were finally at initial values (methane yield around 255 LN CH4 per gram volatile solids of substrate and acetic acid concentration lower than 2 mM). The bacterial communities of the reactors remained stable upon gramine addition. In contrast, the methanogenic community changed from a well-balanced mixture of five phylotypes towards a strong dominance of Methanosarcina (more than two thirds of the methanogenic community) while Methanosaeta disappeared. Batch inhibition assays revealed that acetic acid was only converted to methane via acetoclastic methanogenesis which was more strongly affected by gramine than hydrogenotrophic methanogenesis and acetogenesis. Hence, when acetoclastic methanogenesis is the dominant pathway, a shift of the methanogenic community is necessary to digest gramine-rich plant material. PMID:27138201

  8. Identification and Quantification of the Main Active Anticancer Alkaloids from the Root of Glaucium flavum

    Directory of Open Access Journals (Sweden)

    Lamine Bournine

    2013-12-01

    Full Text Available Glaucium flavum is used in Algerian folk medicine to remove warts (benign tumors. Its local appellations are Cheqiq el-asfar and Qarn el-djedyane. We have recently reported the anti-tumoral activity of Glaucium flavum root alkaloid extract against human cancer cells, in vitro and in vivo. The principal identified alkaloid in the extract was protopine. This study aims to determine which component(s of Glaucium flavum root extract might possess potent antitumor activity on human cancer cells. Quantitative estimation of Glaucium flavum alkaloids was realized by HPLC-DAD. Glaucium flavum effect on human normal and cancer cell viability was determined using WST-1 assay. Quantification of alkaloids in Glaucium flavum revealed that the dried root part contained 0.84% of protopine and 0.07% of bocconoline (w/w, while the dried aerial part contained only 0.08% of protopine, glaucine as the main alkaloid, and no bocconoline. In vitro evaluation of the growth inhibitory activity on breast cancer and normal cells demonstrated that purified protopine did not reproduce the full cytotoxic activity of the alkaloid root extract on cancer cell lines. On the other hand, bocconoline inhibited strongly the viability of cancer cells with an IC50 of 7.8 µM and only a low cytotoxic effect was observed against normal human cells. Our results showed for the first time that protopine is the major root alkaloid of Glaucium flavum. Finally, we are the first to demonstrate a specific anticancer effect of Glaucium flavum root extract against breast cancer cells, which can be attributed, at least in part, to bocconoline.

  9. Effect of Drying Methods on the Steroidal Alkaloid Content of Potato Peels, Shoots and Berries

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    Mohammad B. Hossain

    2016-03-01

    Full Text Available The present study has found that dried potato samples yielded significantly higher levels of steroidal alkaloids such as α-solanine and α-chaconine than the corresponding fresh samples, as determined by the UPLC-MS/MS technique. Among the drying techniques used, air drying had the highest effect on steroidal alkaloid contents, followed by freeze drying and vacuum oven drying. There was no significant difference between the freeze dried and vacuum oven dried samples in their α-chaconine contents. However, freeze dried potato shoots and berries had significantly higher α-solanine contents (825 µg/g dry weight (DW in shoots and 2453 µg/g DW in berries than the vacuum oven dried ones (325 µg/g dry weight (DW in shoots and 2080 µg/g DW in berries. The kinetics of steroidal alkaloid contents of potato shoots during air drying were monitored over a period of 21 days. Both α-solanine and α-chaconine content increased to their maximum values, 875 µg/g DW and 3385 µg/g DW, respectively, after 7 days of drying. The steroidal alkaloid contents of the shoots decreased significantly at day 9, and then remained unchanged until day 21. In line with the potato shoots, air dried potato tuber peels also had higher steroidal alkaloid content than the freeze dried and vacuum oven dried samples. However, a significant decrease of steroidal alkaloid content was observed in air dried potato berries, possibly due to degradation during slicing of the whole berries prior to air drying. Remarkable variation in steroidal alkaloid contents among different tissue types of potato plants was observed with the potato flowers having the highest content.

  10. Effect of Drying Methods on the Steroidal Alkaloid Content of Potato Peels, Shoots and Berries.

    Science.gov (United States)

    Hossain, Mohammad B; Brunton, Nigel P; Rai, Dilip K

    2016-01-01

    The present study has found that dried potato samples yielded significantly higher levels of steroidal alkaloids such as α-solanine and α-chaconine than the corresponding fresh samples, as determined by the UPLC-MS/MS technique. Among the drying techniques used, air drying had the highest effect on steroidal alkaloid contents, followed by freeze drying and vacuum oven drying. There was no significant difference between the freeze dried and vacuum oven dried samples in their α-chaconine contents. However, freeze dried potato shoots and berries had significantly higher α-solanine contents (825 µg/g dry weight (DW) in shoots and 2453 µg/g DW in berries) than the vacuum oven dried ones (325 µg/g dry weight (DW) in shoots and 2080 µg/g DW in berries). The kinetics of steroidal alkaloid contents of potato shoots during air drying were monitored over a period of 21 days. Both α-solanine and α-chaconine content increased to their maximum values, 875 µg/g DW and 3385 µg/g DW, respectively, after 7 days of drying. The steroidal alkaloid contents of the shoots decreased significantly at day 9, and then remained unchanged until day 21. In line with the potato shoots, air dried potato tuber peels also had higher steroidal alkaloid content than the freeze dried and vacuum oven dried samples. However, a significant decrease of steroidal alkaloid content was observed in air dried potato berries, possibly due to degradation during slicing of the whole berries prior to air drying. Remarkable variation in steroidal alkaloid contents among different tissue types of potato plants was observed with the potato flowers having the highest content. PMID:27023503

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

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    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.

  12. Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua.

    Science.gov (United States)

    Hillwig, Matthew L; Zhu, Qin; Liu, Xinyu

    2014-02-21

    Ambiguines belong to a family of hapalindole-type indole alkaloid natural products, with many of the members possessing up to eight consecutive carbon stereocenters in a fused pentacyclic 6-6-6-5-7 ring scaffold. Here, we report the identification of a 42 kbp ambiguine (amb) biosynthetic gene cluster that harbors 32 protein-coding genes in its native producer Fischerella ambigua UTEX1903. Association of the amb cluster with ambiguine biosynthesis was confirmed by both bioinformatic analysis and in vitro characterizations of enzymes responsible for 3-((Z)-2'-isocyanoethenyl) indole and geranyl pyrophosphate biosynthesis and a C-2 indole dimethylallyltransferase that regiospecifically tailors hapalindole G to ambiguine A. The presence of five nonheme iron-dependent oxygenase coding genes (including four Rieske-type oxygenases) within the amb cluster suggests late-stage C-H activations are likely responsible for the structural diversities of ambiguines by regio- and stereospecific chlorination, hydroxylation, epoxidation, and sp(2)-sp(3) C-C bond formation. PMID:24180436

  13. Alcalóides pirrolizidínicos em espécies do gênero Senecio

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    Silva Chana de Medeiros da

    2006-01-01

    Full Text Available Senecio species contain a large variety of secondary metabolites and many of these plants afford pyrrolizidine alkaloids. This paper is a review of the literature, describing 62 pyrrolizidine alkaloids already isolated in 62 of more than 2000 species of Senecio, distributed worldwide. The structure-activity relationships involving their toxicity are also discussed, since some Senecio species used for medicinal purposes are responsible for causing serious adverse effects.

  14. Alcalóides pirrolizidínicos em espécies do gênero Senecio

    Directory of Open Access Journals (Sweden)

    Chana de Medeiros da Silva

    2006-10-01

    Full Text Available Senecio species contain a large variety of secondary metabolites and many of these plants afford pyrrolizidine alkaloids. This paper is a review of the literature, describing 62 pyrrolizidine alkaloids already isolated in 62 of more than 2000 species of Senecio, distributed worldwide. The structure-activity relationships involving their toxicity are also discussed, since some Senecio species used for medicinal purposes are responsible for causing serious adverse effects.

  15. 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

  16. Hydroxyl radical scavenging activities of isoquinoline alkaloids isolated from Coptis chinensis.

    Science.gov (United States)

    Jang, Moon Hee; Kim, Hyun Young; Kang, Ki Sung; Yokozawa, Takako; Park, Jeong Hill

    2009-03-01

    The hydroxyl radical (*OH) scavenging and ferrous ion chelating activities of four isoquinoline alkaloids isolated from Coptis chinensis Franch were studied for the identification of their structural characteristics to scavenge *OH. The *OH was generated via Fe(II)-catalazed Fenton reaction in this study and the reliable measurement of *OH scavenging activities of isoquinoline alkaloids were achieved using electron spin resonance (ESR) spectrometry method. At the 1 mM concentration, berberrubine (85%) showed the strongest *OH scavenging activity and the next were in the decreasing order of coptisine (79%), berberine (23%), and palmatine (22%). The ferrous ion chelating effects of the alkaloids showed similar pattern with their *OH scavenging effects. These results suggest that *OH scavenging effects of the alkaloids were closely related to their ferrous ion chelating activities. In addition, metal chelating functional groups such as hydroxy group at C-9 and methylenedioxy group at C-9 and C-10 were thought to contribute to the *OH scavenging activities of the isoquinoline alkaloids.

  17. Tobacco alkaloids reduction by casings added/enzymatic hydrolysis treatments assessed through PLSR analysis.

    Science.gov (United States)

    Lin, Shunshun; Zhang, Xiaoming; Song, Shiqing; Hayat, Khizar; Eric, Karangwa; Majeed, Hamid

    2016-03-01

    Based on encouraged development of potential reduced-exposure products (PREPs) by the US Institute of Medicine, casings (glucose and peptides) added treatments (CAT) and enzymatic (protease and xylanase) hydrolysis treatments (EHT) were developed to study their effect on alkaloids reduction in tobacco and cigarette mainstream smoke (MS) and further investigate the correlation between sensory attributes and alkaloids. Results showed that the developed treatments reduced nicotine by 14.5% and 24.4% in tobacco and cigarette MS, respectively, indicating that both CAT and EHT are potentially effective for developing lower-risk cigarettes. Sensory and electronic nose analysis confirmed the significant influence of treatments on sensory and cigarette MS components. PLSR analysis demonstrated that tobacco alkaloids were positively correlated to the off-taste, irritation and impact attributes, and negatively correlated to the aroma and softness attributes. Additionally, nicotine and anabasine from tobacco leaves positively contributed to the impact attribute, while they negatively contributed to the aroma attribute (P<0.05). Meanwhile, most alkaloids in cigarette MS positively contributed to the impact and irritation attributes (P<0.05). Hence, this study paved a way to better understand the correlation between tobacco alkaloids and sensory attributes. PMID:26739812

  18. Managing murine food allergy with Cissampelos sympodialis Eichl (Menispermaceae) and its alkaloids.

    Science.gov (United States)

    Costa, Hermann Ferreira; Leite, Fagner Carvalho; Alves, Adriano Francisco; Barbosa-Filho, José Maria; dos Santos, Claudio Roberto Bezerra; Piuvezam, Marcia Regina

    2013-10-01

    Food allergy is a severe human disease with imminent risk of life. Cissampelos sympodialis (Menispermaceae) is a native Brazilian plant used in Brazilian folk medicine for the treatment of respiratory allergies. In this study the experimental model of food allergy induced by ovalbumin (OVA) was used to determine whether the alcoholic extract of the plant (AFL) and its alkaloids match a therapeutic approach for this disease. Animal weight, diarrhea, OVA-specific IgE levels, inflammatory cell and cytokine profiles, mucus production and proportion of T cells on the mesenteric lymph node (MLN) were evaluated. Warifteine (W) or methyl-warifteine (MW) alkaloids slightly improve diarrhea score independently of AFL and all treatments decreased the OVA-specific IgE levels. Stimulated mesenteric lymph node (MLN) cells in the presence of the alkaloids diminished the IL-12p70 levels independently of IFN-γ or IL-13 secretion. The alkaloids increased the number of Treg cells on MLN and reduced the number of eosinophils and mast cells as well as mucus production in the gut. Therefore, the alkaloids modulate the immune response in food allergy by increasing regulatory T cells in MLN independently of Th1 or Th2 profiles. PMID:23810408

  19. Luminescence and binding properties of two isoquinoline alkaloids chelerythrine and sanguinarine with ctDNA

    Science.gov (United States)

    Li, Junfen; Li, Baohong; Wu, Yanbo; Shuang, Shaomin; Dong, Chuan; Choi, Martin M. F.

    2012-09-01

    The binding mode and mechanism of the interactions between two planar cationic alkaloids chelerythrine (Che) and sanguinarine (San) with calf thymus DNA (ctDNA) were systematically investigated at pH 5.40 using UV-vis absorption spectroscopy, fluorescence spectroscopy and cyclic voltammetry. Che and San show strong fluorescence at 570 and 589 nm, respectively. Che displays fluorescence enhancement with ctDNA whereas the fluorescence of San is quenched on interaction with ctDNA. In addition, UV-vis spectra of both alkaloids show apparent hypochromicity and are bathochromic shifted, indicating that they could intercalate into ctDNA bases. The fluorescence polarization of Che and San increases in the presence of ctDNA, again implying the intercalation of two alkaloids with ctDNA. This conclusion was also supported by the results obtained from anion quenching and cyclic voltammetry. The binding constants of both alkaloids with ctDNA were calculated in the order of 105 L/mol. San binds with ctDNA 3-fold stronger than Che. The stoichiometric bindings are five nucleotides per Che or San. Electrostatic binding also exists between the alkaloids and DNA helix. Finally, theoretical calculations show that only certain parts of Che and San molecules intercalate into the DNA helix.

  20. Studies on quantitative determination of total alkaloids and berberine in five origins of crude medicine "Sankezhen".

    Science.gov (United States)

    Li, Luyang; Long, Weifang; Wan, Xiangluan; Ding, Qi; Zhang, Fei; Wan, Dingrong

    2015-02-01

    The roots of Berberis plants are widely used as a traditional Chinese medicine called "Sankezhen", having the activities of antibacterial and anti-inflammatory, and the ingredients are alkaloids. This work aims to study and compare the total alkaloids and individual alkaloid (berberine) contents in roots and stems from five origins of Berberis plants (Berberis soulieana Schneid., B. henryana Schneid., B. triacanthophora Fedde, B. gagnepainii Schneid. and B. bergmanniae Schneid.) and provides some references for resource and quality evaluation of the medicine. Acid dye colorimetry and high-performance liquid chromatography were used in the determination. The results showed that the contents for the total alkaloids in root and stem samples were in the range of 1.60-4.72% and 0.76-2.70%, while those of the berberine were 0.70-2.92% and 0.23-1.07%. With higher contents of the total alkaloids and berberine, the roots of B. soulieana, B. gagnepainii and B. bergmanniae were good sources of "Sankezhen". Meanwhile, the contents were also high in stems of the three plants, indicating that the stems were likely to be alternative sources of "Sankezhen" after further research. As the results of precision, stability and recovery tests shown, the methods were simple, rapid and reliable, and provided valuable basis for quality evaluation and new resource investigation of "Sankezhen". PMID:25013028

  1. Alkaloid Accumulation in Catharanthus roseus Increases with Addition of Seawater Salts to the Nutrient Solution

    Institute of Scientific and Technical Information of China (English)

    WANG Jing-Yan; LIU Zhao-Pu

    2010-01-01

    A sand culture experiment was conducted to determine the effects of different seawater (5% and 10%) treatments on plant growth,inorganic ions,indole alkaloid concentrations and yields of Catharanthus roseus,in an effort to increase the alkaloid yield by artificial cultivation.The total fresh and dry weights and tissue K+ concentrations decreased,but Na+ concentrations increased in the plant roots,stems and leaves of C.roseus under seawater stress as compared to the control.The concentrations and yields of vindoline,catharanthine,vinblastine and vincristine increased under seawater stress.The concentrations and yields of these alkaloids were higher in 5% seawater-treated plants than those in the 10% seawater-treated plants.Considering the industrial production,5% seawater treatments could reduce the cost of producing alkaloid.In the control plants,the highest alkaloid concentrations reached a peak at 100 days after planting,suggesting that plant harvest must be optimized in terms of growth duration.

  2. Qualitative and quantitative analyses of alkaloids in Uncaria species by UPLC-ESI-Q-TOF/MS.

    Science.gov (United States)

    Wang, Hai-Bo; Qi, Wen; Zhang, Lin; Yuan, Dan

    2014-01-01

    An ultra performance liquid chromatography (UPLC) coupled with quadrupole time-of-flight mass spectrometry (Q-TOF/MS) method has been optimized and established for the rapid analysis of the alkaloids in 22 samples originating from five Uncaria (U.) species. The accurate mass measurement of all the protonated molecules and subsequent fragment ions offers higher quality structural information for the interpretation of fragmentation pathways of the various groups of alkaloids. A total of 19 oxindole alkaloids, 16 indole alkaloids and 1 flavone were identified by co-chromatography of the sample extract with authentic standards, comparison of the retention time, characteristic molecular ions and fragment ions, or were tentatively identified by MS/MS determination. Moreover, the method was validated for the simultaneous quantification of the 24 components within 10.5 min. The potential chemical markers were identified for classification of the U. species samples by principal component analysis (PCA) and orthogonal partial least squared discriminant analysis (OPLS-DA). The results demonstrate the similarity and differences in alkaloids among the five U. species, which is helpful for the standardization and quality control of the medical materials of the U. Ramulus Cum Unics (URCU). Furthermore, with multivariate statistical analysis, the determined markers are more definite and useful for chemotaxonomy of the U. genus. PMID:25366313

  3. Acute exposure to ergot alkaloids from endophyte-infected tall fescue does not alter absorptive or barrier function of the isolated bovine ruminal epithelium.

    Science.gov (United States)

    Foote, A P; Penner, G B; Walpole, M E; Klotz, J L; Brown, K R; Bush, L P; Harmon, D L

    2014-07-01

    Ergot alkaloids in endophyte-infected (Neotyphodium coenophialum) tall fescue (Lolium arundinaceum) have been shown to cause a reduction in blood flow to the rumen epithelium as well as a decrease in volatile fatty acids (VFA) absorption from the washed rumen of steers. Previous data also indicates that incubating an extract of endophyte-infected tall fescue seed causes an increase in the amount of VFA absorbed per unit of blood flow, which could result from an alteration in the absorptive or barrier function of the rumen epithelium. An experiment was conducted to determine the acute effects of an endophyte-infected tall fescue seed extract (EXT) on total, passive or facilitated acetate and butyrate flux across the isolated bovine rumen as well as the barrier function measured by inulin flux and tissue conductance (G t ). Flux of ergovaline across the rumen epithelium was also evaluated. Rumen tissue from the caudal dorsal sac of Holstein steers (n=6), fed a common diet, was collected and isolated shortly after slaughter and mounted between two halves of Ussing chambers. In vitro treatments included vehicle control (80% methanol, 0.5% of total volume), Low EXT (50 ng ergovaline/ml) and High EXT (250 ng ergovaline/ml). Results indicate that there is no effect of acute exposure to ergot alkaloids on total, passive or facilitated flux of acetate or butyrate across the isolate bovine rumen epithelium (P>0.51). Inulin flux (P=0.16) and G t (P>0.17) were not affected by EXT treatment, indicating no alteration in barrier function due to acute ergot alkaloid exposure. Ergovaline was detected in the serosal buffer of the High EXT treatment indicating that the flux rate is ~0.25 to 0.44 ng/cm2 per hour. Data indicate that specific pathways for VFA absorption and barrier function of the rumen epithelium are not affected by acute exposure to ergot alkaloids from tall fescue at the concentrations tested. Ergovaline has the potential to be absorbed from the rumen of cattle that

  4. Comparative Analysis of Amaryllidaceae Alkaloids from Three Lycoris Species

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    Yongqiang Tian

    2015-12-01

    Full Text Available The major active constituents from Amaryllidaceae family were reported to be Amaryllidaceae alkaloids (AAs, which exhibited a wide spectrum of biological activities, such as anti-tumor, anti-viral, and acetyl-cholinesterase-inhibitory activities. In order to better understand their potential as a source of bioactive AAs and the phytochemical variations among three different species of Lycoris herbs, the HPLC fingerprint profiles of Lycoris aurea (L. aurea, L. radiata, and L. guangxiensis were firstly determined and compared using LC-UV and LC-MS/MS. As a result, 39 peaks were resolved and identified as AAs, of which nine peaks were found in common for all these three species, while the other 30 peaks could be revealed as characteristic AAs for L. aurea, L. radiata and L. guangxiensis, respectively. Thus, these AAs can be used as chemical markers for the identification and quality control of these plant species. To further reveal correlations between chemical components and their pharmaceutical activities of these species at the molecular level, the bioactivities of the total AAs from the three plant species were also tested against HepG2 cells with the inhibitory rate at 78.02%, 84.91% and 66.81% for L. aurea, L. radiata and L. guangxiensis, respectively. This study firstly revealed that the three species under investigation were different not only in the types of AAs, but also in their contents, and both contributed to their pharmacological distinctions. To the best of our knowledge, the current research provides the most detailed phytochemical profiles of AAs in these species, and offers valuable information for future valuation and exploitation of these medicinal plants.

  5. Calcium antagonist properties of the bisbenzylisoquinoline alkaloid cycleanine.

    Science.gov (United States)

    Martínez, J A; Bello, A; Rubio, L L; Rodríguez, C; Galán, L; Caudales, E; Alvarez, J L

    1998-01-01

    The alkaloid cycleanine ([12aR-(12aR,24aR)]-2,3,12a,13,14,15,24,24a-octa hydro-5,6,17,18- tetramethoxy-1,13-dimethyl-8, 11:20,23-dietheno-1H,12H [1,10]dioxacyclooctadecino[2,3,4-ij:11,12,13-i'j']diisoquinolin e) was extracted from the bulbs of Stephania glabra (Roxb) Miers and its effects on cardiac and smooth muscle preparations were studied and compared to those of nifedipine (1,4-dihydro-2, 6-dimethyl-4-(2-nitrophenyl)-3,5-pyridine dicarboxylic acid dimethylesther). Cycleanine inhibited the KCl-induced contraction of rabbit aortic rings with higher potency than nifedipine. IC50s for cycleanine and nifedipine were 0.8 and 7.10(-9) M respectively. Cycleanine had minor effects on the norepinephrine-induced contraction of rabbit aortic rings. Cycleanine and nifedipine also depressed the contraction of rat ventricular preparations but with lower potency (IC50 = 3 and 0.03.10(-6) M respectively). Action potential duration of rat right ventricular strips was decreased by both compounds. L-type Ca-current (ICaL) of single rat ventricular cardiomyocytes was inhibited by cycleanine in a voltage- and frequency-dependent manner. With a higher potency nifedipine inhibited ICaL in a tonic and almost frequency-independent manner. The results suggest that cycleanine can act as a potent vascular selective Ca-antagonist. PMID:9565772

  6. In Vitro and In Vivo Characterization of the Alkaloid Nuciferine.

    Directory of Open Access Journals (Sweden)

    Martilias S Farrell

    Full Text Available The sacred lotus (Nelumbo nucifera contains many phytochemicals and has a history of human use. To determine which compounds may be responsible for reported psychotropic effects, we used in silico predictions of the identified phytochemicals. Nuciferine, an alkaloid component of Nelumbo nucifera and Nymphaea caerulea, had a predicted molecular profile similar to antipsychotic compounds. Our study characterizes nuciferine using in vitro and in vivo pharmacological assays.Nuciferine was first characterized in silico using the similarity ensemble approach, and was followed by further characterization and validation using the Psychoactive Drug Screening Program of the National Institute of Mental Health. Nuciferine was then tested in vivo in the head-twitch response, pre-pulse inhibition, hyperlocomotor activity, and drug discrimination paradigms.Nuciferine shares a receptor profile similar to aripiprazole-like antipsychotic drugs. Nuciferine was an antagonist at 5-HT2A, 5-HT2C, and 5-HT2B, an inverse agonist at 5-HT7, a partial agonist at D2, D5 and 5-HT6, an agonist at 5-HT1A and D4 receptors, and inhibited the dopamine transporter. In rodent models relevant to antipsychotic drug action, nuciferine blocked head-twitch responses and discriminative stimulus effects of a 5-HT2A agonist, substituted for clozapine discriminative stimulus, enhanced amphetamine induced locomotor activity, inhibited phencyclidine (PCP-induced locomotor activity, and rescued PCP-induced disruption of prepulse inhibition without induction of catalepsy.The molecular profile of nuciferine was similar but not identical to that shared with several approved antipsychotic drugs suggesting that nuciferine has atypical antipsychotic-like actions.

  7. Alkaloid and phenolic compounds of Galanthus caucasicus, Magnolia obovata, Cocculus laurifolius, and Veratrum lobelianum grown in Georgia.

    Science.gov (United States)

    Tsakadze, Dali M; Samsoniya, Shota A; Ziaev, Richsivoi; Abdusamatov, Abdulatip

    2005-01-01

    A collection of plants from the country of Georgia (Galanthus caucasicus, Magnolia obovata, Cocculus laurifolius, and Veratrum lobelianum) has been studied for their alkaloid content. Our studies led to the isolation and identification of 24 alkaloids, three of which are being identified and reported for the first time.

  8. Antibacterial Properties of Alkaloid Extracts from Callistemon citrinus and Vernonia adoensis against Staphylococcus aureus and Pseudomonas aeruginosa.

    Science.gov (United States)

    Mabhiza, Donald; Chitemerere, Tariro; Mukanganyama, Stanley

    2016-01-01

    The development of new antibiotics from new chemical entities is becoming more and more expensive, time-consuming, and compounded by emerging strains that are drug resistant. Alkaloids are plant secondary metabolites which have been shown to have potent pharmacological activities. The effect of alkaloids from Callistemon citrinus and Vernonia adoensis leaves on bacterial growth and efflux pump activity was evaluated on Staphylococcus aureus and Pseudomonas aeruginosa. At a concentration of 1.67 mg/mL, the alkaloids inhibited bacterial growth with comparable effects to ampicillin, a standard antibiotic. The alkaloids from C. citrinus were the most potent against S. aureus with an MIC of 0.0025 mg/mL and MBC of 0.835 mg/mL. It was shown that effects on P. aeruginosa by both plant alkaloids were bacteriostatic. P. aeruginosa was most susceptible to drug efflux pump inhibition by C. citrinus alkaloids which caused an accumulation of Rhodamine 6G of 121% compared to the control. Thus, C. citrinus alkaloids showed antibacterial activity as well as inhibiting ATP-dependent transport of compounds across the cell membrane. These alkaloids may serve as potential courses of compounds that can act as lead compounds for the development of plant-based antibacterials and/or their adjunct compounds. PMID:26904285

  9. Antibacterial Properties of Alkaloid Extracts from Callistemon citrinus and Vernonia adoensis against Staphylococcus aureus and Pseudomonas aeruginosa

    Directory of Open Access Journals (Sweden)

    Donald Mabhiza

    2016-01-01

    Full Text Available The development of new antibiotics from new chemical entities is becoming more and more expensive, time-consuming, and compounded by emerging strains that are drug resistant. Alkaloids are plant secondary metabolites which have been shown to have potent pharmacological activities. The effect of alkaloids from Callistemon citrinus and Vernonia adoensis leaves on bacterial growth and efflux pump activity was evaluated on Staphylococcus aureus and Pseudomonas aeruginosa. At a concentration of 1.67 mg/mL, the alkaloids inhibited bacterial growth with comparable effects to ampicillin, a standard antibiotic. The alkaloids from C. citrinus were the most potent against S. aureus with an MIC of 0.0025 mg/mL and MBC of 0.835 mg/mL. It was shown that effects on P. aeruginosa by both plant alkaloids were bacteriostatic. P. aeruginosa was most susceptible to drug efflux pump inhibition by C. citrinus alkaloids which caused an accumulation of Rhodamine 6G of 121% compared to the control. Thus, C. citrinus alkaloids showed antibacterial activity as well as inhibiting ATP-dependent transport of compounds across the cell membrane. These alkaloids may serve as potential courses of compounds that can act as lead compounds for the development of plant-based antibacterials and/or their adjunct compounds.

  10. 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 frequen

  11. 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

  12. Effects of the ergot alkaloids dihydroergotamine, ergonovine, and ergotamine on growth of Escherichia coli O157:H7 in vitro

    Science.gov (United States)

    A series of experiments were conducted to evaluate the effects of ergot alkaloids (dihydroergotamine, ergonovine, and ergotamine) on E. coli O157:H7 in both pure and mixed ruminal fluid culture. Alkaloids were added to solutions of E. coli O157:H7 strains 933 (pure and ruminal cultures) and 6058 (r...

  13. Rumen microbial abundance and fermentation profile during severe subacute ruminal acidosis and its modulation by plant derived alkaloids in vitro.

    Science.gov (United States)

    Mickdam, Elsayed; Khiaosa-Ard, Ratchaneewan; Metzler-Zebeli, Barbara U; Klevenhusen, Fenja; Chizzola, Remigius; Zebeli, Qendrim

    2016-06-01

    Rumen microbiota have important metabolic functions for the host animal. This study aimed at characterizing changes in rumen microbial abundances and fermentation profiles using a severe subacute ruminal acidosis (SARA) in vitro model, and to evaluate a potential modulatory role of plant derived alkaloids (PDA), containing quaternary benzophenanthridine and protopine alkaloids, of which sanguinarine and chelerythrine were the major bioactive compounds. Induction of severe SARA strongly affected the rumen microbial composition and fermentation variables without suppressing the abundance of total bacteria. Protozoa and fungi were more sensitive to the low ruminal pH condition than bacteria. Induction of severe SARA clearly depressed degradation of fiber (P methanogenic 16S rRNA gene abundance was not affected. According to principal component analysis, Methanobrevibacter spp. correlated to methane concentration. Addition of PDA modulated ruminal fermentation under normal conditions such as enhanced (P < 0.05) concentration of total SCFA, propionate and valerate, and increased (P < 0.05) degradation of crude protein compared with the unsupplemented control diet. Our results indicate strong shifts in the microbial community during severe SARA compared to normal conditions. Supplementation of PDA positively modulates ruminal fermentation under normal ruminal pH conditions. PMID:26868619

  14. Naucline, a New Indole Alkaloid from the Bark of Nauclea officinalis

    Directory of Open Access Journals (Sweden)

    Marc Litaudon

    2012-04-01

    Full Text Available A new indole alkaloid, naucline (1 together with four known alkaloids, angustine (2, angustidine (3, nauclefine (4 and naucletine (5, were isolated from the bark of Nauclea officinalis. The structures of all isolated compounds were elucidated with various spectroscopic methods such as 1D- and 2D- NMR, IR, UV and LCMS-IT-TOF. In addition to that of alkaloid 1, the complete 13C-NMR data of naucletine (5 were also reported. Naucline (1 showed a moderate vasorelaxant activity (90% relaxation at 1 × 10−5 M whereas, angustine (2, nauclefine (4, and naucletine (5 showed potent vasorelaxant activity (more than 90% relaxation at 1 × 10−5 M on an isolated rat aorta.

  15. 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.

  16. Exposure to Ergot Alkaloids During Gestation Reduces Fetal Growth in Sheep

    Science.gov (United States)

    Duckett, Susan; Pratt, Scott; Andrae, John

    2014-08-01

    Tall fescue [Lolium arundinaceum (Schreb.) Darbysh; Schedonorus phoenix (Scop.) Holub] is the primary cool season perennial grass in the eastern U.S. Most tall fescue contains an endophyte (Neotyphodium coenophialum), which produces ergot alkaloids that cause vasoconstriction and could restrict blood flow to the fetus in pregnant animals. The objective of this study was to examine fetal growth during maternal exposure to ergot alkaloids during gestation. Pregnant ewes (n = 16) were randomly assigned to one of two dietary treatments: 1) endophyte-infected (Neotyphodium coenophialum) tall fescue seed (E+; 0.8 ug of ergovaline /g diet DM) and 2) endophyte-free tall fescue seed (E-; 0.0 ug of ergovaline/g diet DM). Birth weight of lambs was reduced by 37% for E+ compared to E-. Organ and muscle weights were also lighter for E+ than E-. Exposure to ergot alkaloids in utero reduces fetal growth and muscle development.

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

    Science.gov (United States)

    Cortinovis, Cristina; Caloni, Francesca

    2015-12-01

    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. PMID:26670251

  18. A QSAR Toxicity Study of a Series of Alkaloids with the Lycoctonine Skeleton

    Directory of Open Access Journals (Sweden)

    Bakhtiyor F. Rasulev

    2004-12-01

    Full Text Available A QSAR toxicity analysis has been performed for a series of 19 alkaloids with the lycoctonine skeleton. GA-MLRA (Genetic Algorithm combined with Multiple Linear Regression Analysis technique was applied for the generation of two types of QSARs: first, models containing exclusively 3D-descriptors and second, models consisting of physicochemical descriptors. As expected, 3D-descriptor QSARs have better statistical fits. Physicochemical-descriptor containing models, that are in a good agreement with the mode of toxic action exerted by the alkaloids studied, have also been identified and discussed. In particular, TPSA (Topological Polar Surface Area and nC=O (number of –C(O– fragments parameters give the best statistically significant mono- and bidescriptor models (when combined with lipophilicity, MlogP confirming the importance of H-bonding capability of the alkaloids for binding at the receptor site.

  19. Isolation of Cells Specialized in Anticancer Alkaloid Metabolism by Fluorescence-Activated Cell Sorting.

    Science.gov (United States)

    Carqueijeiro, Inês; Guimarães, Ana Luísa; Bettencourt, Sara; Martínez-Cortés, Teresa; Guedes, Joana G; Gardner, Rui; Lopes, Telma; Andrade, Cláudia; Bispo, Cláudia; Martins, Nuno Pimpão; Andrade, Paula; Valentão, Patrícia; Valente, Inês M; Rodrigues, José A; Duarte, Patrícia; Sottomayor, Mariana

    2016-08-01

    Plant specialized metabolism often presents a complex cell-specific compartmentation essential to accomplish the biosynthesis of valuable plant natural products. Hence, the disclosure and potential manipulation of such pathways may depend on the capacity to isolate and characterize specific cell types. Catharanthus roseus is the source of several medicinal terpenoid indole alkaloids, including the low-level anticancer vinblastine and vincristine, for which the late biosynthetic steps occur in specialized mesophyll cells called idioblasts. Here, the optical, fluorescence, and alkaloid-accumulating properties of C. roseus leaf idioblasts are characterized, and a methodology for the isolation of idioblast protoplasts by fluorescence-activated cell sorting is established, taking advantage of the distinctive autofluorescence of these cells. This achievement represents a crucial step for the development of differential omic strategies leading to the identification of candidate genes putatively involved in the biosynthesis, pathway regulation, and transmembrane transport leading to the anticancer alkaloids from C. roseus. PMID:27356972

  20. 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.

  1. Improved method for the determination of oxindole alkaloids in Uncaria tomentosa by high performance liquid chromatography.

    Science.gov (United States)

    Ganzera, M; Muhammad, I; Khan, R A; Khan, I A

    2001-07-01

    This Paper describes an improved HPLC method for the determination of pentacyclic oxindole alkaloids in Uncaria tomentosa (Cat's Claw). Six of the isomeric compounds could be baseline separated at room temperature within less than 30 min by using 3 microm C-18 column material and a mobile phase consisting of 10 mM phosphate buffer at pH 7.0 and acetonitrile. At a wavelength of 245 nm all standard compounds could be detected at concentrations as low as 0.63 microg/ml. Different samples of U. tomentosa bark and market products containing Cat's Claw were extracted with a modified procedure ensuring the integrity of the alkaloids and analyzed successfully. The results indicated accuracy and consistency of the new method, and showed variations in the total alkaloid content in products from 0.156 to 0.962%.

  2. Subcellular Localization of Enzymes Involved in Indole Alkaloid Biosynthesis in Catharanthus roseus1

    Science.gov (United States)

    De Luca, Vincenzo; Cutler, Adrian J.

    1987-01-01

    The subcellular localization of enzymes involved in indole alkaloid biosynthesis in leaves of Catharanthus roseus has been investigated. Tryptophan decarboxylase and strictosidine synthase which together produce strictosidine, the first indole alkaloid of this pathway, are both cytoplasmic enzymes. S-Adenosyl-l-methionine: 16-methoxy-2,3-dihydro-3-hydroxytabersonine-N-methyltransferase which catalyses the third to last step in vindoline biosynthesis could be localized in the chloroplasts of Catharanthus leaves and is specifically associated with thylakoids. Acetyl-coenzyme-A-deacetylvindoline-O-acetyltransferase which catalyses the last step in vindoline biosynthesis could also be localized in the cytoplasm. The participation of the chloroplast in this pathway suggests that indole alkaloid intermediates enter and exit this compartment during the biosynthesis of vindoline. PMID:16665811

  3. Two new vinblastine-type N-oxide alkaloids from Catharanthus roseus.

    Science.gov (United States)

    Zhang, Wei-Ku; Xu, Jie-Kun; Tian, Hai-Yan; Wang, Lei; Zhang, Xiao-Qi; Xiao, Xu-Zhi; Li, Ping; Ye, Wen-Cai

    2013-10-01

    Two new vinblastine-type N-oxide alkaloids, 17-desacetoxyvinblastine N'b-oxide (1) and 20'-deoxyvinblastine N'b-oxide (2), were isolated from the leaves of Catharanthus roseus. The structures of 1 and 2 were established by the analysis of their nuclear magnetic resonance and HR-ESI-MS spectroscopic data. All alkaloids were evaluated for their cytotoxic activities against the human hepatocellular carcinoma (HepG2) cell line, human colorectal carcinoma (Lovo) cell line and human breast carcinoma (MCF-7) cell line by the MTT method in vitro, respectively. The results showed that cytotoxic activities of alkaloids 1 and 2 exhibited moderate inhibitory activity on the proliferation of three cancer cells. PMID:23621523

  4. Cases of ergotism in livestock and associated ergot alkaloid concentrations in feed

    Directory of Open Access Journals (Sweden)

    A. Morrie Craig

    2015-02-01

    Full Text Available Ergot-induced disease was known long before Biblical times and has been the root cause for countless human epidemics spanning from the early fourteenth century to the late sixteenth century. In contrast, many of these same ergot alkaloids have been utilized for their medicinal properties to mitigate migraine headaches and have had indications as anticarcinogens. Although ergot alkaloids have been used for centuries, basic pharmacokinetic data has not been documented for clinical disease. Consequently, a threshold dose and accurate dose-response data have yet to be established. Throughout the past several years, new detection techniques have emerged to detect these alkaloids at the parts per billion which have allowed for new efforts to be made with respect to determining threshold levels and making accurate clinical diagnoses. This perspectives article provides a critical initial step for establishing a uniform interpretation of ergot toxicosis from limited existing data.

  5. 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.

  6. Molecular mechanisms of action of herbal antifungal alkaloid berberine, in Candida albicans.

    Directory of Open Access Journals (Sweden)

    Sanjiveeni Dhamgaye

    Full Text Available Candida albicans causes superficial to systemic infections in immuno-compromised individuals. The concomitant use of fungistatic drugs and the lack of cidal drugs frequently result in strains that could withstand commonly used antifungals, and display multidrug resistance (MDR. In search of novel fungicidals, in this study, we have explored a plant alkaloid berberine (BER for its antifungal potential. For this, we screened an in-house transcription factor (TF mutant library of C. albicans strains towards their susceptibility to BER. Our screen of TF mutant strains identified a heat shock factor (HSF1, which has a central role in thermal adaptation, to be most responsive to BER treatment. Interestingly, HSF1 mutant was not only highly susceptible to BER but also displayed collateral susceptibility towards drugs targeting cell wall (CW and ergosterol biosynthesis. Notably, BER treatment alone could affect the CW integrity as was evident from the growth retardation of MAP kinase and calcineurin pathway null mutant strains and transmission electron microscopy. However, unlike BER, HSF1 effect on CW appeared to be independent of MAP kinase and Calcineurin pathway genes. Additionally, unlike hsf1 null strain, BER treatment of Candida cells resulted in dysfunctional mitochondria, which was evident from its slow growth in non-fermentative carbon source and poor labeling with mitochondrial membrane potential sensitive probe. This phenotype was reinforced with an enhanced ROS levels coinciding with the up-regulated oxidative stress genes in BER-treated cells. Together, our study not only describes the molecular mechanism of BER fungicidal activity but also unravels a new role of evolutionary conserved HSF1, in MDR of Candida.

  7. Study of Total Alkaloids from Rhizoma Coptis Chinensis on Experimental Gastric Ulcers

    Institute of Scientific and Technical Information of China (English)

    2005-01-01

    Objective: To study the effects of total alkaloids (TA) extracted from Rhizoma Coptis Chinensis on experimental gastric ulcer models. Methods: Four kinds of experimental ulcer models were established respectively by water-immersion stress, intragastric ethanol, acetic acid erosion, and pylorus ligation. The anti-ulcer effects of TA were evaluated, and compared with that of berberine (Ber) and cimetidine(Cim). Results: TA showed significant inhibitory effects on ulcerative formation induced by water-immersion stress, intragastric ethanol, and pylorus l igation in dose-dependent manner, and showed therapeutic effect on acetic acid erosion-inducing ulcer, in comparison with the control group. The anti-ulcer activity of Ber was less than TA containing equal content of Ber. TA significantly reduced the free acidity, total acidity and total acid output, but didn't affect the gastric juice volume, gastric pepsin activity, adherent mucus quantity of stomach wall and free mucus dissolving in gastric juice. The suppressive activities of TA on gastric acid secretion didn't occur when it was administered into dodecadactylon at a dose of 360 mg/kg wt. Moreover,when compared with Cim, the inhibitory effect of TA on gastric acid secretion isn't proportional to the inhibitory effects on the formation of the 4 kinds of experimental ulcers. Conclusion: TA is a potent candidate in therapeutic drugs for treating gastric ulcer. Its anti-ulcer effective components and mechanism is not only related to Ber and inhibition of gastric acid, but also to other ingredients of TA and mechanism so far unknown.

  8. Thin-Layer Chromatography/Desorption Electrospray Ionization Mass Spectrometry: Investigation of Goldenseal Alkaloids

    Energy Technology Data Exchange (ETDEWEB)

    Van Berkel, Gary J [ORNL; Tomkins, Bruce A [ORNL; Kertesz, Vilmos [ORNL

    2007-01-01

    Desorption electrospray ionization mass spectrometry was investigated as a means to qualitatively identify and to quantify analytes directly from developed normal-phase thin layer chromatography plates. The atmospheric sampling capillary of a commercial ion trap mass spectrometer was extended to permit sampling and ionization of analytes in bands separated on intact TLC plates (up to 10 cm x 10 cm). A surface positioning software package and the appropriate hardware enabled computer-controlled surface scanning along the length of development lanes or at fixed RF value across the plates versus the stationary desorption electrospray emitter. Goldenseal (Hydrastis canadensis) and related alkaloids and commercial dietary supplements were used as standards and samples. Alkaloid standards and samples were spotted and separated on aluminum- or glass-backed plates using established literature methods. The mass spectral signal levels as a function of desorption spray solvent were investigated with acetonitrile proving superior to methanol. The detection levels (ca. 5 ng each or 14 -28 pmol) in mass spectral full scan mode were determined statistically from the calibration curves (2.5 - 100 pmol) for the standards berberine, palmatine and hydrastinine spotted as a mixture and separated on the plates. Qualitative screening of the major alkaloids present in six different over-the-counter "goldenseal" dietary supplements was accomplished by obtaining full scan mass spectra during surface scans along the development lane in the direction of increasing RF value. In one sample, alkaloids were detected that strongly suggested the presence of at least one additional herb undeclared on the product label. These same data indicated the misidentification of one of the alkaloids in the TLC literature. Quantities of the alkaloids present in two of the samples determined using the mass spectral data were in reasonable agreement with the label values indicating the quantitative ability of

  9. 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.

  10. 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.

  11. Characterization of Alkaloid Uptake by Catharanthus roseus (L.) G. Don Protoplasts 1

    Science.gov (United States)

    McCaskill, David G.; Martin, DeAndra L.; Scott, A. Ian

    1988-01-01

    The accumulation of alkaloids by protoplasts of Catharanthus roseus (L.) G. Don var. Little Bright Eye was studied to determine the specificity of uptake and the role of ion trapping in the storage of alkaloids. Accumulation of the indole alkaloids vindoline, ajmalicine, tabersonine, and vinblastine was found to be biphasic, with an initial burst of uptake followed by a slow, prolonged phase of accumulation. The concentration and pH dependence of the initial burst of uptake for vindoline suggested that uptake occurred by simple diffusion. Uptake of nicotine was monophasic, with a half life of 5.2 minutes. The accumulation ratio (Ci/Ce) for nicotine at steady state and for the initial burst of uptake for vindoline and ajmalicine suggested that accumulation was driven by the pH gradient between the vacuole and the external assay medium. The second, sustained phase of uptake of vindoline was sensitive to inhibition by either 20 millimolar NaN3 or 0.5 millimolar Cu2+. In azide-treated protoplasts, the uptake for vindoline conformed to the kinetics of simple diffusion, with a half life of 4 minutes. The second phase of uptake for ajmalicine, although sensitive to inhibition by Cu2+, was insensitive to inhibition by NaN3. The biphasic uptake of the indole alkaloids was not due to any significant metabolism. It is concluded that accumulation and storage of the indole alkaloids is due only partly to ion trapping of the alkaloids by the low pH of the vacuole lumen. In the case of vindoline, there appears to be a specific energy-requiring uptake that is not seen with nicotine (which is not endogenous to Catharanthus). Accumulation of ajmalicine appears to involve both ion trapping and an azide-insensitive component, which may be due to complexation with organic counterions and phenolics. PMID:16666154

  12. Indole Alkaloids from the Sea Anemone Heteractis aurora and Homarine from Octopus cyanea.

    Science.gov (United States)

    Shaker, Kamel H; Göhl, Matthias; Müller, Tobias; Seifert, Karlheinz

    2015-11-01

    The two new indole alkaloids 2-amino-1,5-dihydro-5-(1H-indol-3-ylmethyl)-4H-imidazol-4-one (1), 2-amino-5-[(6-bromo-1H-indol-3-yl)methyl]-3,5-dihydro-3-methyl-4H-imidazol-4-one (2), and auramine (3) have been isolated from the sea anemone Heteractis aurora. Both indole alkaloids were synthesized for the confirmation of the structures. Homarine (4), along with uracil (5), hypoxanthine (6), and inosine (7) have been obtained from Octopus cyanea.

  13. 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.

    concise synthesis of (R)-Bgugaine, a pyrrolidine alkaloid from arisarum vulgare Mahesh S. Majik a , P.S. Parameswaran b and Santosh G. Tilve a * a Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India b National Institute... and effective chiral catalysts. 2-4 There are a large number of studies concerning the development of new syntheses of these molecules. 5-7 (R)-Bgugaine (1) is a natural 2-alkyl pyrrolidine alkaloid, first isolated 8 in 1993 from the tubers...

  14. Unified Synthesis of 10-Oxygenated Lycopodium Alkaloids: Impact of C10-Stereochemistry on Reactivity.

    Science.gov (United States)

    Saha, Mrinmoy; Li, Xin; Collett, Nathan D; Carter, Rich G

    2016-07-15

    The pronounced impact of the C10 stereochemistry on the successful construction of a polycyclic Lycopodium alkaloid scaffold has been explored. A wide range of reaction conditions and functionality were investigated to control a keto sulfone Michael addition to construct the C7-C12 linkage. An unexpected, overriding impact of the C10 stereochemistry in stereoselectivity and reaction rate in the Michael addition was observed. Furthermore, divergent reactivity of a conformationally accelerated, intramolecular Mannich cyclization based on the C10 stereochemistry was discovered. The successful execution of this synthetic route resulted in the total synthesis of all three known 10-oxygenated Lycopodium alkaloids: 10-hydroxylycopodine, paniculine, and deacetylpaniculine. PMID:27353498

  15. Antiviral alkaloids produced by the mangrove-derived fungus Cladosporium sp. PJX-41.

    Science.gov (United States)

    Peng, Jixing; Lin, Tao; Wang, Wei; Xin, Zhihong; Zhu, Tianjiao; Gu, Qianqun; Li, Dehai

    2013-06-28

    Six new indole alkaloids including five new glyantrypine derivatives (1, 2a, 2b, 3, 4) and a new pyrazinoquinazoline derivative (5), together with eight known alkaloids (6-13), were isolated from the culture of the mangrove-derived fungus Cladosporium sp. PJX-41. Their structures were elucidated primarily by spectroscopic and physical data. The absolute configurations of compounds 1-9 were established on the basis of CD, NOESY data, and single-crystal X-ray diffraction analysis. Compounds 2b, 5, 7-9, and 11 exhibited significant activities against influenza virus A (H1N1), with IC50 values of 82-89 μM.

  16. 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)

  17. Two New Koumine-Type Indole Alkaloids from Gelsemium elegans Benth.

    Directory of Open Access Journals (Sweden)

    Huanhuan Gao

    2013-01-01

    Full Text Available Two new indole alkaloids, 21-oxokoumine (1 and furanokoumine (2, were isolated from the roots of Gelsemium elegans Benth together with three known compounds. The structures of the two novel compounds were elucidated by spectroscopic methods, including NMR, HR-ESI-MS, UV, IR, CD and molecular modeling. Compound 1 is the first instance of a koumine-type alkaloid with a carbonyl at the C-21 position, while compound 2 possesses a tetrahydrofuran ring located on C-20 and C-21.

  18. 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 ...

  19. Unlocking the diversity of alkaloids in Catharanthus roseus: nuclear localization suggests metabolic channeling in secondary metabolism.

    Science.gov (United States)

    Stavrinides, Anna; Tatsis, Evangelos C; Foureau, Emilien; Caputi, Lorenzo; Kellner, Franziska; Courdavault, Vincent; O'Connor, Sarah E

    2015-03-19

    The extraordinary chemical diversity of the plant-derived monoterpene indole alkaloids, which include vinblastine, quinine, and strychnine, originates from a single biosynthetic intermediate, strictosidine aglycone. Here we report for the first time the cloning of a biosynthetic gene and characterization of the corresponding enzyme that acts at this crucial branchpoint. This enzyme, an alcohol dehydrogenase homolog, converts strictosidine aglycone to the heteroyohimbine-type alkaloid tetrahydroalstonine. We also demonstrate how this enzyme, which uses a highly reactive substrate, may interact with the upstream enzyme of the pathway. PMID:25772467

  20. Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel

    OpenAIRE

    Sun, Liang; Veith, Jean M.; Pera, Paula; Bernacki, Ralph J.; Ojima, Iwao

    2010-01-01

    Novel paclitaxel-mimicking alkaloids were designed and synthesized based on a bioactive conformation of paclitaxel, i.e., REDOR-Taxol. The alkaloid 2 bearing a 5-7-6 tricyclic scaffold mimics REDOR-Taxol best among the compounds designed and was found to be the most potent compound against several drug-sensitive and drug-resistant human cancer cell lines. MD simulation study on the paclitaxel mimics 1 and 2 as well as REDOR-Taxol bound to the 1JFF tubulin structure was quite informative to ev...

  1. Natural Aristolactams and Aporphine Alkaloids as Inhibitors of CDK1/Cyclin B and DYRK1A

    Directory of Open Access Journals (Sweden)

    Françoise Guéritte

    2013-03-01

    Full Text Available In an effort to find potent inhibitors of the protein kinases DYRK1A and CDK1/Cyclin B, a systematic in vitro evaluation of 2,500 plant extracts from New Caledonia and French Guyana was performed. Some extracts were found to strongly inhibit the activity of these kinases. Four aristolactams and one lignan were purified from the ethyl acetate extracts of Oxandra asbeckii and Goniothalamus dumontetii, and eleven aporphine alkaloids were isolated from the alkaloid extracts of Siparuna pachyantha, S. decipiens, S. guianensis and S. poeppigii. Among these compounds, velutinam, aristolactam AIIIA and medioresinol showed submicromolar IC50 values on DYRK1A.

  2. Four new tetracyclic alkaloids with cis-decahydroquinoline motif from Myrioneuron effusum.

    Science.gov (United States)

    Zhang, Jia-Hui; Guo, Jing-Jing; Yuan, Yu-Xi; Fu, Yan-Hui; Gu, Yu-Cheng; Zhang, Yu; Chen, Duo-Zhi; Li, Shun-Lin; Di, Ying-Tong; Hao, Xiao-Jiang

    2016-07-01

    Four new Myrioneuron alkaloids, mysumamides A-D (1-4), along with three known ones were isolated from the twigs and leaves of Myrioneuron effusum. All of these alkaloids possessed the tetracyclic skeleton and contained the decahydroquinoline (cis-DHQ) moiety. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR techniques. The absolute configuration of 1 was determined by single-crystal X-ray diffraction. The cytotoxic activities of these compounds were also evaluated in vitro. PMID:27316979

  3. Scientific Opinion on Ergot alkaloids in food and feed

    Directory of Open Access Journals (Sweden)

    EFSA Panel on Contaminants in the Food Chain

    2012-07-01

    Full Text Available

    The European Food Safety Authority (EFSA was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread Claviceps species within the Hypocreales. A total of 20 558 analytical results for EAs in 1 716 food, 496 feed and 67 unprocessed grain samples were considered in this opinion. Based on the EAs identified in sclerotia of C. purpurea, and recent literature data, the EFSA Panel on Contaminants in the Food Chain (CONTAM Panel based its risk assessment on the main C. purpurea EAs, namely ergometrine, ergotamine, ergosine, ergocristine, ergocryptine (which is a mixture of α- and β- isomers, ergocornine, and the corresponding –inine epimers. The CONTAM Panel performed estimates of both chronic and acute exposure for various age groups across European countries. A BMDL10 of 0.33 mg/kg b.w. per day was calculated for the incidence of tail muscular atrophy in a 13-week rat feeding study of ergotamine. This effect was considered representative of the vasoconstrictive effects of EAs and provided a suitable reference point for establishment of a group acute reference dose of 1 μg/kg body weight (b.w. and a group tolerable daily intake of 0.6 μg/kg b.w. per day. The Panel concluded that whilst the available data do not indicate a concern for any population subgroup, the dietary exposure estimates relate to a limited number of food groups and a possible unknown contribution from other foods cannot be discounted. Estimates of exposure for livestock based on example diets and levels of EAs in cereal grains reported suggest that under normal conditions the risk of toxicosis is low.

  4. Characterization of the variation in the imidazole alkaloid profile of Pilocarpus microphyllus in different seasons and parts of the plant by electrospray ionization mass spectrometry fingerprinting and identification of novel alkaloids by tandem mass spectrometry.

    Science.gov (United States)

    Abreu, Iika N; Mazzafera, Paulo; Eberlin, Marcos N; Zullo, Marco António T; Sawaya, Alexandra C H F

    2007-01-01

    Pilocarpus microphyllus (Rutaceae), popularly known as jaborandi, is the only commercial source of an imidazole alkaloid named pilocarpine. In the present study, the variation in the profile of imidazole alkaloids in different seasons and in different parts of the P. microphyllus plant during the summer was analyzed by electrospray ionization mass spectrometry in the positive ion mode [ESI(+)-MS]. The fingerprints of these extracts repeatedly presented similar ions which were mass-selected and studied by tandem mass spectrometry (ESI-MS/MS and ESI-MS/MS/MS) and high-resolution mass spectrometry, resulting in the characterization of eight imidazole alkaloids. The data from the ESI(+)-MS fingerprints were analyzed by principal component analysis (PCA), showing that pilocarpine was present mainly in the summer, whereas in the autumn mainly pilosine and winter anhydropilosine were found. Three alkaloids, reported for the first time in extracts of P. microphyllus, were found. Analysis of the distribution of alkaloids in different parts of the plant during the summer showed that, although pilocarpine was present throughout the plant, 13-nor-8(11)-dihydropilocarpine was found mainly in the stem, pilosine and anhydropilosine were present mainly in the intermediary leaves, and the three new alkaloids were mainly found in the leaflets and petioles. Based on the dissociation patterns of these alkaloids, we observed that there were three structurally related groups of alkaloids differing in their distribution in the plant tissues and responding differently to seasonal variations. These results also indicate that these three groups of alkaloids could belong to intermediate, parallel or competitive pathways for pilocarpine formation biosynthesis. PMID:17330216

  5. Qualitative and quantitative analysis of an alkaloid fraction from Piper longum L. using ultra-high performance liquid chromatography-diode array detector-electrospray ionization mass spectrometry.

    Science.gov (United States)

    Li, Kuiyong; Fan, Yunpeng; Wang, Hui; Fu, Qing; Jin, Yu; Liang, Xinmiao

    2015-05-10

    In a previous research, an alkaloid fraction and 18 alkaloid compounds were prepared from Piper longum L. by series of purification process. In this paper, a qualitative and quantitative analysis method using ultra-high performance liquid chromatography-diode array detector-mass spectrometry (UHPLC-DAD-MS) was developed to evaluate the alkaloid fraction. Qualitative analysis of the alkaloid fraction was firstly completed by UHPLC-DAD method and 18 amide alkaloid compounds were identified. A further qualitative analysis of the alkaloid fraction was accomplished by UHPLC-MS/MS method. Another 25 amide alkaloids were identified according to their characteristic ions and neutral losses. At last, a quantitative method for the alkaloid fraction was established using four marker compounds including piperine, pipernonatine, guineensine and N-isobutyl-2E,4E-octadecadienamide. After the validation of this method, the contents of above four marker compounds in the alkaloid fraction were 57.5mg/g, 65.6mg/g, 17.7mg/g and 23.9mg/g, respectively. Moreover, the relative response factors of other three compounds to piperine were calculated. A comparative study between external standard quantification and relative response factor quantification proved no remarkable difference. UHPLC-DAD-MS method was demonstrated to be a powerful tool for the characterization of the alkaloid fraction from P. longum L. and the result proved that the quality of alkaloid fraction was efficiently improved after appropriate purification.

  6. Extraction Optimization of Tinospora cordifolia and Assessment of the Anticancer Activity of Its Alkaloid Palmatine

    Directory of Open Access Journals (Sweden)

    Huma Ali

    2013-01-01

    Full Text Available Objective. To optimize the conditions for the extraction of alkaloid palmatine from Tinospora cordifolia by using response surface methodology (RSM and study its anticancerous property against 7,12-dimethylbenz(aanthracene (DMBA induced skin carcinogenesis in Swiss albino mice. Methods. The effect of three independent variables, namely, extraction temperature, time, and cycles was investigated by using central composite design. A single topical application of DMBA (100 μg/100 μL of acetone, followed 2 weeks later by repeated application of croton oil (1% in acetone three times a week for 16 weeks, exhibited 100 percent tumor incidence (Group 2. Results. The highest yield of alkaloid from Tinospora cordifolia could be achieved at 16 hours of extraction time under 40°C with 4 extraction cycles. Alkaloid administration significantly decreases tumor size, number, and the activity of serum enzyme when compared with the control (Group 2. In addition, depleted levels of reduced glutathione (GSH, superoxide dismutase (SOD, and catalase and increased DNA damage were restored in palmatine treated groups. Conclusion. The data of the present study clearly indicate the anticancer potential of palmatine alkaloid in DMBA induced skin cancer model in mice.

  7. Analysis of several irdoid and indole precursors of terpenoid indole alkaloids with a single HPLC run

    DEFF Research Database (Denmark)

    Dagnino, Denise; Schripsema, Jan; Verpoorte, Robert

    1996-01-01

    An isocratic HPLC system is described which allows the separation of the iridoid and indole precursors of terpenoid indole alkaloids, which are present in a single crude extract. The system consists of a column of LiChrospher 60 RP select B 5 my, 250x4 mm (Merck) with an eluent of 1 % formic acid...

  8. Synthesis of the C(18) -norditerpenoid alkaloid neofinaconitine: a lesson in convergent synthesis planning.

    Science.gov (United States)

    Liu, Xiao-Yu; Chen, David Y-K

    2014-01-20

    Hexacyclic framework: The total synthesis of the complex C18 -norditerpenoid alkaloid neofinaconitine has been achieved by a convergent approach. This remarkable synthesis featured two Diels-Alder cycloadditions and subsequent Mannich-type N-acyliminium and radical cyclizations to establish the unique hexacyclic core structure of the target molecule.

  9. Separation and enrichment of major quinolizidine type alkaloids from Sophora alopecuroides using macroporous resins.

    Science.gov (United States)

    Yang, Jin; Zhang, Liyan; Zhu, Guihua; Li, Li

    2014-01-15

    Matrine (MT), oxymatrine (OM) and sophoridine (SP) are three bioactive alkaloids in Sophora alopecuroides. In the present study, the chromatographic characteristics of six widely used macroporous resins, namely NKA, NKA-9, HPD-100, HPD-722, HPD-750, and AB-8, respectively, towards the separation and enrichment of the three alkaloids from the aqueous extract of S. alopecuroides are critically evaluated. The results indicated that AB-8 resin offered the best absorption and desorption capacity and its adsorption data fitted best to the Freundlich isotherm. Dynamic adsorption and desorption experiments on packed columns of AB-8 resin have been investigated for optimization of chromatographic parameters. The adsorption of the alkaloids on the resin was best achieved by 5 bed volume (BV) of sample solution of pH 10 with a flow rate of 2BV/h. The desorption of the compounds from the resin was effectively completed by using 5BV of 80% ethanol in water at a flow rate of 2BV/h. After one run of adsorption and desorption, the contents of MT, OM, and SP were increased from 9.30, 8.39 and 9.84% to 22.22, 21.44 and 28.02%, the recovery were 69.4, 78.3 and 72.6%, respectively. This method would provide useful information to the industrial production of the alkaloids from S. alopecuroides. PMID:24321756

  10. Rigidin E, a New Pyrrolopyrimidine Alkaloid from a Papua New Guinea Tunicate Eudistoma Species

    Directory of Open Access Journals (Sweden)

    Rohan A. Davis

    2003-11-01

    Full Text Available Abstract: A new pyrrolopyrimidine alkaloid, rigidin E (1 and the known metabolites rigidin (2 and 1-methylherbipoline (3 have been isolated from a Papua New Guinea tunicate Eudistoma sp. A combination of spectroscopic data were used to determine the structures of these metabolites.

  11. Rigidin E, a New Pyrrolopyrimidine Alkaloid from a Papua New Guinea Tunicate Eudistoma Species

    Science.gov (United States)

    Davis, Rohan A.; Christensen, Lane V.; Richardson, Adam D.; da Rocha, Rosana Moreira; Ireland, Chris M.

    2003-01-01

    A new pyrrolopyrimidine alkaloid, rigidin E (1) and the known metabolites rigidin (2) and 1-methylherbipoline (3) have been isolated from a Papua New Guinea tunicate Eudistoma sp. A combination of spectroscopic data were used to determine the structures of these metabolites.

  12. Horizontal acquisition of toxic alkaloid synthesis in a clade of plant associated fungi.

    Science.gov (United States)

    Marcet-Houben, Marina; Gabaldón, Toni

    2016-01-01

    Clavicipitaceae is a fungal group that comprises species that closely interact with plants as pathogens, parasites or symbionts. A key factor in these interactions is the ability of these fungi to synthesize toxic alkaloid compounds that contribute to the protection of the plant host against herbivores. Some of these compounds such as ergot alkaloids are toxic to humans and have caused important epidemics throughout history. The gene clusters encoding the proteins responsible for the synthesis of ergot alkaloids and lolines in Clavicipitaceae have been elucidated. Notably, homologs to these gene clusters can be found in distantly related species such as Aspergillus fumigatus and Penicillium expansum, which diverged from Clavicipitaceae more than 400 million years ago. We here use a phylogenetic approach to analyze the evolution of these gene clusters. We found that the gene clusters conferring the ability to synthesize ergot alkaloids and loline emerged first in Eurotiomycetes and were then likely transferred horizontally to Clavicipitaceae. Horizontal gene transfer is known to play a role in shaping the distribution of secondary metabolism clusters across distantly related fungal species. We propose that HGT events have played an important role in the capability of Clavicipitaceae to produce two key secondary metabolites that have enhanced the ability of these species to protect their plant hosts, therefore favoring their interactions. PMID:26688468

  13. Three New Tazettine-Type Alkaloids from Galanthus gracilis and Galanthus plicatus Subsp. byzantinus.

    Science.gov (United States)

    Unver, N; Noyan, S; Gözler, T; Onür, M A; Gözler, B; Hesse, M

    1999-05-01

    Three new tazettine-type alkaloids were isolated from two different GALANTHUS species of Turkish origin. (+)-Isotazettinol and (+)-3- O-demethylmacronine are obtained from G. GRACILIS, while (+)-3- O-demethyl-3-epimacronine is found in G. PLICATUS subsp. BYZANTINUS. The known base, trispheridine, is reported for the first time in GALANTHUS genus.

  14. 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.

  15. 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...

  16. Study on adsorptive separation of berberine alkaloids in Coptis Japonica makino by molecular dynamics simulation

    Energy Technology Data Exchange (ETDEWEB)

    Wang, D.; Sakoda, A.; Suzuki, M. [University of Tokyo, Tokyo (Japan). Institure of Industrial Science

    1997-12-01

    A calculation approach to discuss the solvent effect on liquid phase adsorption has been developed by using the molecular dynamics simulation method and solvophobic theory. The distinctive feature of the approach is that the calculations of the potential energy changes related to the solvent effect can be achieved on the basis of the molecular structure only, without using any experimental physicochemical property of the solute. This approach is applied to adsorption of five berberine alkaloids contained in Coptis japonica Makino onto the graphite surface from six solvents. Detailed analysis of the potential energy changes due to the solvent effect derived by molecular dynamics calculations yields an outline of the relative adsorption capacities of the alkaloids. Furthermore, the prediction of the preferential adsorption of alkaloids onto a graphite surface from the liquid phase and the eluent strength of solvents for desorption of the alkaloids from graphite surface were obtained. The calculated results are in good agreement with experimental data. 25 refs., 11 figs., 4 tabs.

  17. Norditerpenoid Alkaloids from the Roots of Aconitum hemsleyanum Pritz.var.Pengzhouense

    Institute of Scientific and Technical Information of China (English)

    ChongShengPENG; FengPengWANG; 等

    2002-01-01

    In continuation of our studies on Aconitum hemsleyanum Pritz.var. pengzhouense, two new norditerpenoid alkaloids, pengshenines A(1) and B(2),have isolated from the roots of the plants and their strucures were elucidated by 1D-and 2D-NMR.

  18. Seasonal accumulation of major alkaloids in organs of pharmaceutical crop Narcissus Carlton

    NARCIS (Netherlands)

    Lubbe, A.; Gude, H.; Verpoorte, R.; Choi, C.Y.

    2013-01-01

    Narcissus pseudonarcissus (L.) cv. Carlton is being cultivated as a main source of galanthamine from the bulbs. After galanthamine, haemanthamine and narciclasine are the next most abundant alkaloids in this cultivar. Both these compounds are promising chemical scaffolds for potential anticancer dru

  19. Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

    DEFF Research Database (Denmark)

    Soman De Medeiros, Lívia; da Silva, José Vinícius; Abreu, Lucas Magalhães;

    2015-01-01

    UHPLC-DAD-HRMS based dereplication guided the detection of new halogenated alkaloids co-produced by Talaromyces wortmannii. From the fungal growth in large scale, the epimers 2,8-dichlororugulovasines A and B were purified and further identified by means of a HPLC-SPE/NMR hyphenated system...

  20. Analysis of the Aconitine Alkaloids in Chuanwu by Electrospray Ionization/Tandem Mass Spectrometry

    Institute of Scientific and Technical Information of China (English)

    Ai Min SUN; Hui LI; Zhi Ming HUANG; P.P.H.BUT; Xue Qin DING

    2004-01-01

    An electrospray ionization / tandem mass spectrometric (ESI/MS/MS) method was developed for the simultaneous identification and analysis of three aconitine alkaloids [ mesacontine (MA), hypaconitine (HA), and aconitine (A)] as intact molecules at low nanogram level in Chinese traditional medicine Chuanwu decoction as well as in human whole blood extract without chromatographic separation.