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Sample records for cinchona

  1. Composition of the endophytic filamentous fungi associated with Cinchona ledgeriana seeds and production of Cinchona alkaloids.

    Science.gov (United States)

    Maehara, Shoji; Agusta, Andria; Kitamura, Chinami; Ohashi, Kazuyoshi; Shibuya, Hirotaka

    2016-04-01

    Four kinds of endophytic filamentous fungi (code names: CLS-1, CLS-2, CLS-3, and CLS-4) associated with the seeds of Cinchona ledgeriana (Rubiaceae) from West Java, Indonesia, were isolated. All of the isolates were classified into Diaporthe spp. based on phylogenetic analysis of the nucleotide sequences of the internal transcribed spacers (ITS1 and ITS2) including the 5.8S ribosomal DNA region. All four of these endophytic fungi produce Cinchona alkaloids, mainly quinine and quinidine, in synthetic liquid medium. PMID:26645397

  2. Fused triazoles via tandem reactions of activated Cinchona alkaloids with azide ion. Second Cinchona rearrangement exemplified.

    Science.gov (United States)

    Röper, S; Franz, M H; Wartchow, R; Hoffmann, H M R

    2003-08-01

    [reaction: see text] Intramolecular 1,3-dipolar cycloadditions of cinchona azides to the C10-C11 alkyne and C10-C11 olefin unit of the alkaloid have been designed via tandem strategy. A variety of fused triazoles and triazolines with a bis-azahomotwistane skeleton have been prepared. In trifluoroethanol, O-mesylcinchonidine 7-OMs and NaN(3) furnish triazole 8 as well as cage-expanded 1,5-diazatricyclo[4.4.1.0(3,8)]undecane derivative 10. Both fused triazoles 8 and 10 are formed with retention of configuration at C9 and C3, respectively. 1-Azabicyclo[3.2.2]cage expansion is shown to be reversible. PMID:12889871

  3. Quinine, Malaria, and the Cinchona Bureau: Marketing Practices and Knowledge Circulation in a Dutch Transoceanic Cinchona-Quinine Enterprise (1920s-30s).

    Science.gov (United States)

    Van Der Hoogte, Arjo Roersch; Pieters, Toine

    2016-04-01

    In this study, we will show how a Dutch pharmaceutical consortium of cinchona producers and quinine manufacturers was able to capitalize on one of the first international public health campaigns to fight malaria, thereby promoting the sale of quinine, an antimalarial medicine. During the 1920s and 1930s, the international markets for quinine were controlled by this Dutch consortium, which was a transoceanic cinchona-quinine enterprise centered in the Cinchona Bureau in the Netherlands. We will argue that during the interwar period, the Cinchona Bureau became the decision-making center of this Dutch cinchona-quinine pharmaceutical enterprise and monopolized the production and trade of an essential medicine. In addition, we will argue that capitalizing on the international public health campaign in the fight against malaria by the Dutch cinchona-quinine enterprise via the Cinchona Bureau can be regarded as an early example of corporate colonization of public health by a private pharmaceutical consortium. Furthermore, we will show how commercial interests prevailed over scientific interests within the Dutch cinchona-quinine consortium, thus interfering with and ultimately curtailing the transoceanic circulation of knowledge in the Dutch empire.

  4. Quinine, Malaria, and the Cinchona Bureau: Marketing Practices and Knowledge Circulation in a Dutch Transoceanic Cinchona-Quinine Enterprise (1920s-30s).

    Science.gov (United States)

    Van Der Hoogte, Arjo Roersch; Pieters, Toine

    2016-04-01

    In this study, we will show how a Dutch pharmaceutical consortium of cinchona producers and quinine manufacturers was able to capitalize on one of the first international public health campaigns to fight malaria, thereby promoting the sale of quinine, an antimalarial medicine. During the 1920s and 1930s, the international markets for quinine were controlled by this Dutch consortium, which was a transoceanic cinchona-quinine enterprise centered in the Cinchona Bureau in the Netherlands. We will argue that during the interwar period, the Cinchona Bureau became the decision-making center of this Dutch cinchona-quinine pharmaceutical enterprise and monopolized the production and trade of an essential medicine. In addition, we will argue that capitalizing on the international public health campaign in the fight against malaria by the Dutch cinchona-quinine enterprise via the Cinchona Bureau can be regarded as an early example of corporate colonization of public health by a private pharmaceutical consortium. Furthermore, we will show how commercial interests prevailed over scientific interests within the Dutch cinchona-quinine consortium, thus interfering with and ultimately curtailing the transoceanic circulation of knowledge in the Dutch empire. PMID:26054829

  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. 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.

  7. [Historical research of cinchona cultivation in Japan (Part 3)--A proposal to introduce cinchona by Takeaki Enomoto].

    Science.gov (United States)

    Nagumo, Seiji; Izawa, Kazuo

    2010-01-01

    We attempted to determine how one of the most valuable medicinal plants, cinchona, was brought to and cultivated in Japan. In the course of the study, we report that cinchona seedlings were brought to Japan for the first time in 1876, as per Takeaki Enomoto's proposal to the Meiji government. We also examine the details of his proposal in effort to clarify that the written proposal was submitted between February and March, 1874, and considered his motives leading to the submission. Cinchona is a very important medicinal plant that has saved human lives. However, there was no proof that Takeaki Enomoto's proposal made it introduction to Japan possible, nor was there any evidence that its cultivation was attempted. In addition, it was not clear that the details of the above has been found in document including the Nomutenmatsu (agricultural report published by the Meiji Government). It is significant that the details has been clarified by our series of studies not only from the standpoint of the history of pharmacy, but also from the accounts of the great predecessors involved, such as Takeaki Emonoto and Yasusade Tashiro.

  8. 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.

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

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    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.

  10. Quinine, Malaria, and the Cinchona Bureau : Marketing Practices and Knowledge Circulation in a Dutch Transoceanic Cinchona-Quinine Enterprise (1920s-30s)

    NARCIS (Netherlands)

    Roersch van der Hoogte, Arjo; Pieters, Toine

    2015-01-01

    In this study, we show how a Dutch pharmaceutical consortium of cinchona producers and quinine manufacturers was able to capitalize on one of the first international public health campaigns to fight malaria, thereby promoting the sale of quinine, an antimalarial medicine. During the 1920s and 1930s,

  11. Nature's Chiral Catalyst and Anti-Malarial Agent: Isolation and Structure Elucidation of Cinchonine and Quinine from "Cinchona calisaya"

    Science.gov (United States)

    Carroll, Anne-Marie; Kavanagh, David J.; McGovern, Fiona P.; Reilly, Joe W.; Walsh, John J.

    2012-01-01

    Nature is a well-recognized source of compounds of interest, but access is often an issue. One pertinent example is the cinchona alkaloids from the bark of "Cinchona calisaya." In this experiment, students at the third-year undergraduate level undertake the selective isolation and characterization of two of the four main alkaloids present in the…

  12. Origins of stereoselectivity in intramolecular aldol reactions catalyzed by cinchona amines.

    Science.gov (United States)

    Lam, Yu-Hong; Houk, K N

    2015-02-11

    The intramolecular aldol condensation of 4-substituted heptane-2,6-diones leads to chiral cyclohexenones. The origins of the enantioselectivities of this reaction, disclosed by List et al. using a cinchona alkaloid-derived primary amine (cinchona amine) organocatalyst, have been determined with dispersion-corrected density functional theory (DFT). The stereocontrol hinges on the chair preference of the substrate-enamine intermediate and the conformational preferences of a hydrogen-bonded nine-membered aldol transition state containing eight heavy atoms. The conformations of the hydrogen-bonded ring in the various stereoisomeric transition structures have been analyzed in detail and shown to closely resemble the conformers of cyclooctane. A model of stereoselectivity is proposed for the cinchona amine catalysis of this reaction. The inclusion of Grimme's dispersion corrections in the DFT calculations (B3LYP-D3(BJ)) substantially improves the agreement of the computed energetics and experiment, attesting to the importance of dispersion effects in stereoselectivity. PMID:25629689

  13. Synthesis, structure and in vitro cytostatic activity of ferrocene-Cinchona hybrids.

    Science.gov (United States)

    Kocsis, László; Szabó, Ildikó; Bősze, Szilvia; Jernei, Tamás; Hudecz, Ferenc; Csámpai, Antal

    2016-02-01

    Exploring copper(I)- and ruthenium(II)-catalyzed azide-alkyne cycloadditions and a Sonogashira protocol, novel cytostatic ferrocene-cinchona hybrids were synthetized displaying significant in vitro activity on HepG-2 and HT-29 cells. Preliminary SAR studies disclosed that compounds incorporating linkers with 1,2,3-triazole and chalchone residues can be considered as promising lead structures. According to the best of our knowledge this is the first letter on the incorporation of ferrocene nucleus in the reputed cinchona family via triazole and chalcone linkers with established pharmaceutical profile. PMID:26739780

  14. Distribución de Alcaloides en la Corteza de Algunas Cinchonas Peruanas

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    Hodge W. H.

    1946-08-01

    Full Text Available Los análisis de las muestras seleccionadas de corteza de quinas silvestres que crecían,en el Perú indican que el contenido en alcaloides varía apreciablemente según la posición de la base a los puntos más altos del árbol. En algunos tipos de cinchonas los alcaloides se encuentran en mayor cantidad en la base del tronco que en las partes más altas del árbol pero, en otros tipos de cinchona ocurre lo inverso. Por lo tanto para determinar el rendimiento comercial deben tomarse muestras de estas dos partes del árbol. También aparece cierta relación entre la cantidad de alcaloides presentes en un árbol y su circunferencia (o edad. La cantidad de alcaloides aumenta o disminuye según aumente o disminuya el diámetro y dicha relación depende del alcaloide y del tipo de cinchona.

  15. Crystal structure of quinine: the effects of vinyl and methoxy groups on molecular assemblies of Cinchona alkaloids cannot be ignored.

    Science.gov (United States)

    Hisaki, Ichiro; Hiraishi, Eri; Sasaki, Toshiyuki; Orita, Hideo; Tsuzuki, Seiji; Tohnai, Norimitsu; Miyata, Mikiji

    2012-11-01

    Quinine, one of Cinchona alkaloids, has been of great interest from medical, synthetic, and supramolecular viewpoints. However, unaccountably, the guest-free (GF) crystal of quinine containing no solvent or other molecules has not been reported for nearly three decades, although GF crystals of other Cinchona alkaloids, such as quinidine, cinchonidine, and cinchonine, are already known. In this study, we successfully revealed the crystal structure of quinine, which belongs to the P2(1) space group with the cell parameters of a=6.0587(1), b=19.2492(5), c=22.2824(7) Å, β=92.1646(11)°, and V=2596.83(12) Å(3). Interestingly, the crystal has three crystallographically independent molecules in the cell (Z'=3) that are connected through a N(quinoline)⋅⋅⋅H-O hydrogen bond to form a pseudo three-two-fold (3(2)) double-helical motif. The helical motif is completely different from those observed in GF crystals of other Cinchona alkaloids. Hierarchical comparison on the crystal structures of a series of Cinchona alkaloids including quinine clearly demonstrated that only small structural differences of a molecule, particularly the position of the vinyl group, cause a significant variety of assembly manner in the crystalline state. There have been no reports systematically demonstrating such steric effect in crystals of Cinchona alkaloids, and, therefore, the present system contributes to the design of desired functional crystal structures.

  16. 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...

  17. Novel cinchona carbamate selectors with complementary enantioseparation characteristics for N-acylated amino acids.

    Science.gov (United States)

    Krawinkler, Karl Heinz; Maier, Norbert M; Ungaro, Rocco; Sansone, Francesco; Casnati, Alessandro; Lindner, Wolfgang

    2003-01-01

    The synthesis and chromatographic evaluation of the enantiomer separation capabilities of covalently immobilized calix[4]arene-cinchona carbamate hybrid type receptors derived from quinine (QN) and its corresponding C9-epimer (eQN) in different solvents are reported. The receptors display complementary enantiomer separation profiles in terms of elution order, chiral substrate specificity, and mobile phase characteristics, indicating the existence of two distinct chiral recognition mechanisms. The QN-derived receptor binds the (S)-enantiomers of N-acylated amino acids more strongly, shows preferential recognition of open-chained amino acids, and superior enantioselectivity in polar media such as methanol/acetic acid. In contrast, the eQN congener preferentially recognizes the corresponding (R)-enantiomers, displays good enantioselectivity (alpha up to 1.74) for cyclic amino acids, and enhanced stereodiscriminating properties in apolar mobile phases, e.g., chloroform/acetic acid. A comparison of the enantiomer separation profiles with those of the corresponding QN and eQN tert-butyl carbamate congeners indicates no significant level of cooperativity between the calix[4]arene module and the cinchona units in terms of overall chiral recognition, most probably as a consequence of residual conformational flexibility of the calixarene module and the carbamate linkage.

  18. 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.

  19. Salts of phenylacetic acid and 4-hydroxyphenylacetic acid with Cinchona alkaloids: Crystal structures, thermal analysis and FTIR spectroscopy

    Science.gov (United States)

    Amombo Noa, Francoise M.; Jacobs, Ayesha

    2016-06-01

    Seven salts were formed with phenylacetic acid (PAA), 4-hydroxyphenylacetic acid (HPAA) and the Cinchona alkaloids; cinchonidine (CIND), quinidine (QUID) and quinine (QUIN). For all the structures the proton was transferred from the carboxylic acid of the PAA/HPAA to the quinuclidine nitrogen of the respective Cinchona alkaloid. For six of the salts, water was included in the crystal structures with one of these also incorporating an isopropanol solvent molecule. However HPAA co-crystallised with quinine to form an anhydrous salt, (HPAA-)(QUIN+). The thermal stability of the salts were determined and differential scanning calorimetry revealed that the (HPAA-)(QUIN+) salt had the highest thermal stability compared to the other salt hydrates. The salts were also characterized using Fourier transform infrared spectroscopy. (PAA-)(QUID+)·H2O and (PAA-)(QUIN+)·H2O are isostructural and Hirshfeld surface analysis was completed to compare the intermolecular interactions in these two structures.

  20. Iron(III) protoporphyrin IX complexes of the antimalarial Cinchona alkaloids quinine and quinidine.

    Science.gov (United States)

    de Villiers, Katherine A; Gildenhuys, Johandie; le Roex, Tanya

    2012-04-20

    The antimalarial properties of the Cinchona alkaloids quinine and quinidine have been known for decades. Surprisingly, 9-epiquinine and 9-epiquinidine are almost inactive. A lack of definitive structural information has precluded a clear understanding of the relationship between molecular structure and biological activity. In the current study, we have determined by single crystal X-ray diffraction the structures of the complexes formed between quinine and quinidine and iron(III) protoporphyrin IX (Fe(III)PPIX). Coordination of the alkaloid to the Fe(III) center is a key feature of both complexes, and further stability is provided by an intramolecular hydrogen bond formed between a propionate side chain of Fe(III)PPIX and the protonated quinuclidine nitrogen atom of either alkaloid. These interactions are believed to be responsible for inhibiting the incorporation of Fe(III)PPIX into crystalline hemozoin during its in vivo detoxification. It is also possible to rationalize the greater activity of quinidine compared to that of quinine.

  1. Science, industry and the colonial state : a shift from a German- to a Dutch-controlled cinchona and quinine cartel (1880–1920)

    NARCIS (Netherlands)

    Roersch van der Hoogte, Arjo; Pieters, Toine

    2015-01-01

    This study shows how control over delicately balanced supply chains from raw material to the final product shifted from one national industry to another. By 1920, Dutch cinchona producers and quinine manufacturers dominated the international cartel that controlled the worldwide production and distri

  2. Science in the service of colonial agro-industrialism: the case of cinchona cultivation in the Dutch and British East Indies, 1852-1900.

    Science.gov (United States)

    Roersch van der Hoogte, Arjo; Pieters, Toine

    2014-09-01

    The isolation of quinine from cinchona bark in 1820 opened new possibilities for the mass-production and consumption of a popular medicine that was suitable for the treatment of intermittent (malarial) fevers and other diseases. As the 19th century European empires expanded in Africa and Asia, control of tropical diseases such as malaria was seen as crucial. Consequently, quinine and cinchona became a pivotal tool of British, French, German and Dutch empire-builders. This comparative study shows how the interplay between science, industry and government resulted in different historical trajectories for cinchona and quinine in the Dutch and British Empires during the second half of the 19th century. We argue that in the Dutch case the vectors of assemblage that provided the institutional and physical framework for communication, exchange and control represent an early example of commodification of colonial science. Furthermore, both historical trajectories show how the employment of the laboratory as a new device materialised within the colonial context of agricultural and industrial production of raw materials (cinchona bark), semi-finished product (quinine sulphate) and plant-based medicines like quinine. Hence, illustrating the 19th century transition from 'colonial botany' and 'green imperialism' to what we conceptualise as 'colonial agro-industrialism'. PMID:24981994

  3. Science in the service of colonial agro-industrialism : the case of cinchona cultivation in the Dutch and British East Indies, 1852-1900

    NARCIS (Netherlands)

    Roersch van der Hoogte, Arjo; Pieters, Toine

    2014-01-01

    The isolation of quinine from cinchona bark in 1820 opened new possibilities for the mass-production and consumption of a popular medicine that was suitable for the treatment of intermittent (malarial) fevers and other diseases. As the 19th century European empires expanded in Africa and Asia, contr

  4. Cinchona alkaloid squaramide catalyzed enantioselective hydrazination/cyclization cascade reaction of α-isocyanoacetates and azodicarboxylates: synthesis of optically active 1,2,4-triazolines.

    Science.gov (United States)

    Zhao, Mei-Xin; Bi, Hong-Lei; Zhou, Hao; Yang, Hui; Shi, Min

    2013-09-20

    An efficient enantioselective hydrazination/cyclization cascade reaction of α-substituted isocyanoacetates to azodicarboxylates catalyzed by Cinchona alkaloid derived squaramide catalysts has been investigated, affording the optically active 1,2,4-triazolines in excellent yields (up to 99%) and good to excellent enantioselectivities (up to 97% ee) under mild conditions. PMID:23984761

  5. From Colonial Agro-Industrialism to agro-industrialism : Game-changing evolution of the Dutch transoceanic cinchona-quinine Enterprise (1940's-1960s)

    NARCIS (Netherlands)

    Pieters, A.H.L.M.

    2016-01-01

    By the turn of the twentieth century, the Dutch colony of the Netherlands Indies dominated the worldwide supply of antifebrifuge (to reduce fever) cinchona bark, the raw material for quinine, an antimalarial medicine. Over the next four decades, the high-quality and laboratory-conditioned cultivatio

  6. Rapid and Green Analytical Method for the Determination of Quinoline Alkaloids from Cinchona succirubra Based on Microwave-Integrated Extraction and Leaching (MIEL Prior to High Performance Liquid Chromatography

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    Farid Chemat

    2011-11-01

    Full Text Available Quinas contains several compounds, such as quinoline alkaloids, principally quinine, quinidine, cinchonine and cichonidine. Identified from barks of Cinchona, quinine is still commonly used to treat human malaria. Microwave-Integrated Extraction and Leaching (MIEL is proposed for the extraction of quinoline alkaloids from bark of Cinchona succirubra. The process is performed in four steps, which ensures complete, rapid and accurate extraction of the samples. Optimal conditions for extraction were obtained using a response surface methodology reached from a central composite design. The MIEL extraction has been compared with a conventional technique soxhlet extraction. The extracts of quinoline alkaloids from C. succirubra obtained by these two different methods were compared by HPLC. The extracts obtained by MIEL in 32 min were quantitatively (yield and qualitatively (quinine, quinidine, cinchonine, cinchonidine similar to those obtained by conventional Soxhlet extraction in 3 hours. MIEL is a green technology that serves as a good alternative for the extraction of Cinchona alkaloids.

  7. Regulación en el uso de la tierra con fines preventivos en los alrededores del cuadrante de la antigua comunidad de Cinchona, Alajuela, Costa Rica

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    Esquivel Valverde, Lidier

    2011-07-01

    Full Text Available La regulación del uso de la tierra permite establecer cuales lugares son aptas para el establecimiento de zonas habitacionales, comercios, industria, actividades agrícolas, actividades turísticas, entre otras, evitando incrementar la vulnerabilidad física o ambiental. El presente artículo se basa en un estudio realizado a la comunidad de Cinchona a raíz del sismo del año 2009, el cual, por las características topográficas y geológicas de la región, generó una cantidad alta de daños a la infraestructura y pérdida de vidas humanas, lo que propició la elaboración de una herramienta técnica normativa que regulara el uso de la tierra en esa zona. La investigación consideró aspectos como el uso de la tierra antes del sismo, tenencia de la tierra, producción agropecuaria, valor de la tierra, pendientes de terreno, geomorfología, capacidad de uso de la tierra, aguas subterráneas, zonas de vida y áreas silvestres y por último las amenazas más relevantes. Como resultado del estudio se presenta en el artículo un resumen de la regulación de tierra propuesta, la cual comprende el sector de Vieja Cinchona (zona devastada por el sismo y las microcuencas cercanas Land use regulations allow to identify suitable places to establish housing, commerce, industry, agricultural activities, and tourism, among others, avoiding to increase physical or environmental vulnerability. This article is based on a study developed at the Cinchona community after the 2009 earthquake, which due to the topographic and geological characteristics generated a lot of damages to infrastructures and losses of human lives. In this context, a normative technical tool was developed to regulate the land use in the zone. The investigation considered aspects such as land use before the earthquake, land possession, farming production, land value, land slopes, geomorphology, land use capacity, underground water, wild life areas and most relevant threats. As a result of

  8. [The complex travel of cinchona barks between Peru and Québec Hôtel-Dieu, in the middle of the eighteenth century].

    Science.gov (United States)

    Simon, Lorène; Lafont, Olivier

    2016-03-01

    Duplessis sisters, who were religious nuns in Hôtel-Dieu (Quebec hospital), were exchanging letters with a French apothecary from Dieppe in Normandy, named Jacques-Tranquilain Féret. They asked him to send them in Quebec the drugs and medicines their apothecary needed. Amongst these drugs were cinchona barks that came from Callao in Peru by boat, passed Cape Horn and then sailed to Cadiz, the great Spanish port. Then they embarked to Rouen, which was the French port for goods coming from overseas. The goods from Peru had then to be transported on little fishing boats to Dieppe, where Féret received the barks. The apothecary sent these drugs to Quebec by boats sailing either from Rouen or from La Rochelle. So these Peruvian drugs had to cross two times the Ocean before accessing to North America. PMID:27281933

  9. [The complex travel of cinchona barks between Peru and Québec Hôtel-Dieu, in the middle of the eighteenth century].

    Science.gov (United States)

    Simon, Lorène; Lafont, Olivier

    2016-03-01

    Duplessis sisters, who were religious nuns in Hôtel-Dieu (Quebec hospital), were exchanging letters with a French apothecary from Dieppe in Normandy, named Jacques-Tranquilain Féret. They asked him to send them in Quebec the drugs and medicines their apothecary needed. Amongst these drugs were cinchona barks that came from Callao in Peru by boat, passed Cape Horn and then sailed to Cadiz, the great Spanish port. Then they embarked to Rouen, which was the French port for goods coming from overseas. The goods from Peru had then to be transported on little fishing boats to Dieppe, where Féret received the barks. The apothecary sent these drugs to Quebec by boats sailing either from Rouen or from La Rochelle. So these Peruvian drugs had to cross two times the Ocean before accessing to North America.

  10. Procesos de ladera cosísmicos del terremoto de Cinchona (Costa Rica del 8 de enero de 2009 (Ms= 6,2

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    Adolfo Quesada Román

    2016-02-01

    Full Text Available The Cinchona earthquake of January 8, 2009, caused great physical impacts such as the destruction of the public and private infrastructure, including social, and left a total of 2,326 persons displaced, 91 injured, 7 missing, and 25 dead. Based on aerial photographs and the implementation of high resolution LiDAR, after the earthquake, 1,900 hillside processes were classified based on the Works of Alcántara- Ayala (2000, Cruden and Varnes (1996 and Highland y Bobrowsky (2008. The importance of this work for Costa Rica lies in the fact that it is the first time the international classification of hillside processes of the WP/WLI established in 1990 was used.

  11. Avaliação de parâmetros de extração da Cinchona Vahl por métodos farmacopéicos e não farmacopéicos Extraction parameters from Cinchona pubescens Vahl using pharmacopeia and no pharmacopeia methods

    Directory of Open Access Journals (Sweden)

    Iarah Daniela Dantas Silva

    2009-09-01

    Full Text Available O presente estudo teve como objetivo a otimização de parâmetros cinéticos de extração da Cinchona pubescens Vahl por ultra-som, usando métodos farmacopéicos e não farmacopéicos. Na extração por ultrasom variaram-se o tempo, a massa, a faixa granulométrica, o volume de solvente e o tipo de solvente. Na decocção, as extrações foram feitas no tempo e temperatura descrita na Farmacopéia Brasileira IV, variando-se o sistema solvente. Na extração por maceração variaram-se o tempo e o sistema solvente. O teor de alcalóides quinolínicos foi monitorado por espectrofotometria no UV a 325 nm. O método decocção foi o que apresentou o maior rendimento na extração dos alcalóides, dados equivalentes foram conseguidos com o método ultra-som, no tempo de 5 min e solvente acidificado pH 4, com um rendimento maior ao da maceração. Pela aplicação do planejamento fatorial para o método do ultra-som foi visto que há uma interação entre as variáveis, necessitando de um melhor ajuste entre elas a fim de melhorar a eficiência extrativa do método do ultra-som.The present study for ultrasound had as objective the optimization of kinetic parameters of extraction of the Cinchona pubescens Vahl, using pharmacopeia and no pharmacopeia methods. In the extraction for ultrasound they had varied the time, the solvent type, the mass, the volume of solvent and grain size of the sample. In the decoction, the extractions had been made according to the time and temperature described in Brazilian Pharmacopeia IV, varying the solvent system. In the extraction for maceration the time and the solvent system had varied. The alkali of the Cinchona pubescens Vahl, was monitored by spectrophotometry in UV 325 nm. The method decoction was the one that presented the biggest income in the alkaloids extraction, given equivalent data had been obtained with the method ultrasound, in the solvent acidified pH 4 and time of 5 min, with a bigger income than the

  12. Avaliação de parâmetros de extração da Cinchona Vahl por métodos farmacopéicos e não farmacopéicos Extraction parameters from Cinchona pubescens Vahl using pharmacopeia and no pharmacopeia methods

    OpenAIRE

    Iarah Daniela Dantas Silva; Cícero Flávio Soares Aragão

    2009-01-01

    O presente estudo teve como objetivo a otimização de parâmetros cinéticos de extração da Cinchona pubescens Vahl por ultra-som, usando métodos farmacopéicos e não farmacopéicos. Na extração por ultrasom variaram-se o tempo, a massa, a faixa granulométrica, o volume de solvente e o tipo de solvente. Na decocção, as extrações foram feitas no tempo e temperatura descrita na Farmacopéia Brasileira IV, variando-se o sistema solvente. Na extração por maceração variaram-se o tempo e o sistema solven...

  13. Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.

    Science.gov (United States)

    Liu, Yu; Li, Li; Zhang, Heng-Yi; Fan, Zhi; Guan, Xu-Dong

    2003-02-01

    The inclusion complexation behavior of chiral members of cinchona alkaloid with beta- and gamma-cyclodextrins (1 and 2) and 6,6(')-trimethylenediseleno-bridged bis(beta-cyclodextrin) (3) was assessed by means of fluorescence and 2D-NMR spectroscopy. The spectrofluorometric titrations have been performed in aqueous buffer solution (pH 7.20) at 25.0 degrees C to determine the stability constants of the inclusion complexation of 1-3 with guest molecules (i.e., cinchonine, cinchonidine, quinine, and quinidine) in order to quantitatively investigate the molecular selective binding ability. The stability constants of the resulting complexes of 2 with guest molecules are larger than that of 1. As a result of cooperative binding, the stability constants of inclusion complexation of dimeric beta-cyclodextrin 3 with cinchonidine and cinchonine are higher than that of parent 1 by factor of 4.5 and 2.4, respectively. These results are discussed from the viewpoint of the size-fit and geometric complementary relationship between the host and guest.

  14. High-performance liquid chromatographic enantioseparation of cyclic β-aminohydroxamic acids on zwitterionic chiral stationary phases based on Cinchona alkaloids.

    Science.gov (United States)

    Lajkó, Gyula; Orosz, Tímea; Grecsó, Nóra; Fekete, Beáta; Palkó, Márta; Fülöp, Ferenc; Lindner, Wolfgang; Péter, Antal; Ilisz, István

    2016-05-19

    Cyclic β-aminohydroxamic acid enantiomer pairs were stereoselectively separated by high-performance liquid chromatography on the recently developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+)™, ZWIX(-)™, ZWIX(+A) and ZWIX(-A). The results of variation of the applied chromatographic conditions, such as the bulk solvent composition, the concentrations and ratio of the acid and base additives, the presence of water as mobile phase additive and the counter-ion concentration furnished a better understanding of the retention mechanism. A thermodynamic study in the temperature range 5-50 °C revealed enthalpy-controlled enantiodiscrimination in all cases. The structure-selectivity relationships clearly indicated the importance of the strereochemistry of the functional groups. From an enantiorecognition aspect, the diexo position of the functional groups always proved more favorable than the diendo position. The elution sequence was determined in all cases and was found to reversed when ZWIX(+)™ was changed to ZWIX(-)™ or ZWIX(+A) to ZWIX(-A).

  15. Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds.

    Science.gov (United States)

    Grecsó, Nóra; Kohout, Michal; Carotti, Andrea; Sardella, Roccaldo; Natalini, Benedetto; Fülöp, Ferenc; Lindner, Wolfgang; Péter, Antal; Ilisz, István

    2016-05-30

    The enantiomers of trans-paroxetine were separated on four chiral stationary phases (CSPs) based on chiral zwitterionic Cinchona alkaloids fused with (R,R)- or (S,S)-trans-2-aminocyclohexanesulfonic acid. The enantioseparations were carried out in polar-ionic or in hydro-organic mobile phases with MeOH/THF, MeCN/THF, MeCN/THF/H2O and MeOH/MeCN/THF containing organic acid and base additives, in the temperature range 0-50°C. The effects of the mobile phase composition, the natures and concentrations of the additives and temperature on the separations were investigated. Thermodynamic parameters were calculated from plots of ln α vs 1/T. Δ(ΔH°) ranged between -3.0 and +1.5 kJ mol(-1), and Δ(ΔS°) between -8.8 and +5.9 J mol(-1)K(-1). The enantioseparation was generally enthalpically controlled, the retention factor and separation factor decreasing with increasing temperature, but entropically controlled separation was also observed. The elution sequences of the paroxetine enantiomers on the two pairs of pseudo-enantiomeric CSPs were investigated, and an attempt was made to explain the observed anomalies in silico in order to gain an insight into the underlying molecular recognition events between the four chiral selectors and the analyte enantiomers. PMID:26955754

  16. Novel urea-linked cinchona-calixarene hybrid-type receptors for efficient chromatographic enantiomer separation of carbamate-protected cyclic amino acids.

    Science.gov (United States)

    Krawinkler, Karl Heinz; Maier, Norbert M; Sajovic, Elisabeth; Lindner, Wolfgang

    2004-10-22

    Two novel diastereomeric cinchona-calixarene hybrid-type receptors (SOs) were synthesized by inter-linking 9-amino(9-deoxy)-quinine (AQN)/9-amino(9-deoxy)-epiquinine (eAQN) and a calix[4]arene scaffold via an urea functional unit. Silica-supported chiral stationary phases (CSPs) derived from these SOs revealed, for N-protected amino acids, complementary chiral recognition profiles in terms of elution order and substrate specificity. The AQN-derived CSP showed narrow-scoped enantioselectivity for open-chained amino acids bearing pi-acidic aromatic protecting groups, preferentially binding the (S)-enantiomers. In contrast, the eAQN congener exhibited broad chiral recognition capacity for open-chained as well as cyclic amino acids, and preferential binding of the (R)-enantiomers. Exceedingly strong retention due to nonenantioselective hydrophobic analyte-calixarene interactions observed with hydro-organic mobile phases could be largely suppressed with organic mobile phases containing small amounts of acetic acid as acidic modifier. With the eAQN-calixarene hybrid-type CSP particularly high levels of enantioselectivity could be achieved for tert-butoxycarbonyl (Boc)-, benzyloxycarbonyl (Z)- and fluorenylmethoxycarbonyl (Fmoc)-protected cyclic amino acids using chloroform as mobile phase, e.g. an enantioselectivty factor alpha >5.0 for Boc-proline. Increasing amounts of acetic acid compromised enantioselectivity, indicating the crucial contributions of hydrogen bonding to chiral recognition. Comparison of the performance characteristics of the urea-linked eAQN-calixarene hybrid-type CSP with those of structurally closely related mutants provided evidence for the active involvement of the urea and calixarene units in the chiral recognition process. The urea linker motif was shown to contribute to analyte binding via multiple hydrogen bonding interactions, while the calixarene module is believed to support stereodiscrimination by enhancing the shape complementarity of the

  17. Antimalarial substances of an endophytic fungus isolated from cinchona tree%一株具有抗疟活性的金鸡纳树内生真菌的研究

    Institute of Scientific and Technical Information of China (English)

    周松林; 陈双林; 黄风迎; 王华; 赵焕阁

    2013-01-01

    为筛选具抗疟疾活性的的内生真菌,采用平板分离法对海南金鸡那树内生真菌进行分离纯化.利用“4日抑制疟疾”测试内生真菌发酵液的抗疟活性,采用TLC、HPLC等分析技术对内生菌发酵液等成分进行分析.从金鸡那树叶片分离到31种内生真菌,通过筛选找到了1株具有抗疟疾活性的产奎宁或奎宁类似物的内生真菌.从金鸡那树叶片中分离得到1株产奎宁的结实串孢霉属内生真菌,为奎宁的资源开发开辟了新途径.%Plate method was used to isolate and purify endophytic fungi from Cinchona sp. in Hainan Province. The anti-malaria activity of fermented liquid of the endophytic fungi was tested using "4 day inhibit malaria", and the components such as quinine or structural analogues were analysed using TLC and HPLC. Of the 31 endophytic species isolated from cinchona tree one strain producing quinine or quinine analogues with antimalarial activity was obtained. Morphological observation indicated that this endophytic fungus could be identified as Hormiscium sp.

  18. Application of cinchona-sulfonate-based chiral zwitterionic ion exchangers for the separation of proline-containing dipeptide rotamers and determination of on-column isomerization parameters from dynamic elution profiles

    Energy Technology Data Exchange (ETDEWEB)

    Wernisch, Stefanie, E-mail: stefanie.wernisch@univie.ac.at [Institute for Analytical Chemistry, University of Vienna, Währinger Straße 38, A-1090 Vienna (Austria); Trapp, Oliver, E-mail: trapp@oci.uni-heidelberg.de [Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg (Germany); Lindner, Wolfgang, E-mail: wolfgang.lindner@univie.ac.at [Institute for Analytical Chemistry, University of Vienna, Währinger Straße 38, A-1090 Vienna (Austria)

    2013-09-17

    Graphical abstract: -- Highlights: •X-Pro peptides produce interconverting elution profiles on zwitterionic stationary phases. •The cis–trans isomerization rate in solution is lower than in the chromatographic system. •Cinchona-based zwitterionic selectors apparently lower the isomerization barrier. •Rotamer separation is feasible <0 °C, enantiomer separation above room temperature. -- Abstract: The interconversion of cis and trans isomers of dipeptides containing C-terminal proline was studied by dynamic chromatography on zwitterionic chiral stationary phases at temperatures ranging from −15 °C to +45 °C The cis–trans isomers could be separated below 0 °C and above 0–10 °C plateau formation and peak coalescence phenomena occurred, which is characteristic for a dynamic process at the time-scale of partitioning. At and above room temperature, full coalescence was observed, which allowed separations of enantiomers without interference from interconversion effects. Analysis of the dynamic elution profiles of the interconverting peptides allowed the determination of isomerization rate constants and thermodynamic activation parameters (isomerization enthalpy, entropy and activation energy). In accordance with established results, isomerization rates and thermodynamic parameters were found to depend on the nature of the N-terminal amino acid. Isomerization barriers were only slightly lower than values determined with other methods but significant differences in the relative contributions of the activation enthalpy and entropy as well as isomerization rates pointed toward selector-moderated isomerization dynamics.

  19. 金鸡纳生物碱-9-O-三甲基硅衍生物催化的不对称“中断”Feist-Bénary反应%Cinchona Alkaloid-9-O-trimethylsilyl Derivatives as Organocatalysts for the Asymmetric Interrupted” Feist-Bénary Reaction

    Institute of Scientific and Technical Information of China (English)

    金瑛; 张天一; 昌盛

    2012-01-01

    Cinchona alkaloid-9-0-trimethylsilyl(TMS) derivatives have been used to catalyze the asymmetric interrupted " Feist-B6nary reaction of ethyl bromopyruvate/substituted bromo-ketoesters with 1,3-cyclohexadione. The corresponding hydroxydihydrofurans have been obtained in excellent yields (85% ~ 97% ) and with up to 90% ee value.%将6种金鸡纳生物碱-9-O-三甲基硅(TMS)衍生物用于催化环己二酮与溴乙酰甲酸乙酯/β取代的溴乙酰甲酸乙酯的不对称“中断的”Feist-Bénary反应,得到了高的化学产率(85%~97%)和最高达90%ee的立体选择性.

  20. 金鸡纳生物碱-9-O-脯氨酸酯衍生物催化的不对称“中断的”Feist-Bénary反应%Cinchona alkaloid-9-O-proline ester derivatives as organocatalysts for asymmetric “ interrupted” Feist-Bénary reaction

    Institute of Scientific and Technical Information of China (English)

    张天一; 张巍; 李妍; 金瑛

    2012-01-01

    4种金鸡纳生物碱-9-O-脯氨酸酯衍生物用于催化环己二酮与溴乙酰甲酸乙酯的不对称“中断的”Feist-Bénary反应,得到了高的化学产率(>92%)和最高为72% e.e.的立体选择性.%Four cinchona alkaloid-9-O-proline ester derivatives were used to catalyze the asymmetric " interrupted " Feist-B6nary reaction of ethyl bromopyruvate bromo-ketoesters and 1,3-cyclohexadione. The corresponding hydroxydihydro-furans were obtained in excellent yields ( > 92% ) and with up to 72% e. e. .

  1. Fluorescence studies of some protonated cinchona alkaloids in polymers

    Energy Technology Data Exchange (ETDEWEB)

    Kumar Joshi, Neeraj; Rautela, Ranjana [Photophysics Laboratory, Department of Physics, D.S.B. Campus, Kumaun University, Nainital 263002 (India); Joshi, Hem Chandra, E-mail: hem_sup@yahoo.co.u [Institute for Plasma Research, Laser Diagnostics Division, Bhat, Near Indira Bridge, Gandhinagar, Gujarat 382428 (India); Pant, Sanjay, E-mail: sanjaypent@yahoo.co [Photophysics Laboratory, Department of Physics, D.S.B. Campus, Kumaun University, Nainital 263002 (India)

    2011-07-15

    In the present paper we report spectral and photophysical properties of two probes viz. cinchonidine and quinidine in two different polymers viz. polyvinyl alcohol (PVA) and polymethylmethacrylate (PMMA). The emission spectra exhibit edge excitation red shift (EERS) for both the probes and multiexponential decays are observed. Presence of various conformers and geometries is suggested to explain the observed results. The photophysical properties and excited state behavior of Cd++ are more sensitive towards the microenvironment of the polymer. - Research highlights: {yields} We report photophysical properties of cinchonidine and quinidine in PMMA and PVA. {yields} The emission spectra exhibit edge excitation red shift and multiexponential decays. {yields} Presence of conformers and geometries is suggested to explain the observed results.

  2. Excited state proton transfer in the Cinchona alkaloid cupreidine

    NARCIS (Netherlands)

    J. Qian; A.M. Brouwer

    2010-01-01

    Photophysical properties of the organocatalyst cupreidine (CPD) and its chromophoric building block 6-hydroxyquinoline (6HQ) in protic and nonprotic polar solvents (methanol and acetonitrile) were investigated by means of UV-vis absorption, and steady state and time resolved fluorescence spectroscop

  3. Drug: D08460 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available gif Cinchona [TAX:43462], Cinchona calisaya [TAX:153742], Cinchona succirubra, Cinchona calisaya Antiprotozoa...[BR:br08302] Antiparasitics Antiprotozoals Quinine D08460 Quinine (BAN) Antiinfectives [BR:br08307] Antipara

  4. An efficient, robust, and inexpensive grinding device for herbal samples like Cinchona bark

    DEFF Research Database (Denmark)

    Hansen, Steen Honoré; Holmfred, Else Skovgaard; Cornett, Claus;

    2015-01-01

    An effective, robust, and inexpensive grinding device for the grinding of herb samples like bark and roots was developed by rebuilding a commercially available coffee grinder. The grinder was constructed to be able to provide various particle sizes, to be easy to clean, and to have a minimum of d...

  5. Enantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst.

    Science.gov (United States)

    Shao, Qian; Chen, Jiean; Tu, Meihua; Piotrowski, David W; Huang, Yong

    2013-12-01

    An enantioselective organocatalytic process for the one-step synthesis of poly-substituted 1,2,4-triazolines is reported. The heterocycle formation is believed to go through a step-wise mechanism of nucleophilic addition of an azlactone to an azodicarboxylate in the presence of an organic base catalyst, followed by a TMSCHN2 mediated heterocyclization. Both theoretical calculations and experimental evidence suggest the pre-organization of the transition state for the chirality determining step via a unique 7-membered intramolecular hydrogen bonding. PMID:24145477

  6. Synthesis of Chiral Chalcone Derivatives Catalyzed by the Chiral Cinchona Alkaloid Squaramide

    Directory of Open Access Journals (Sweden)

    Dandan Xie

    2014-11-01

    Full Text Available An effective method has been developed for the preparation of novel chiral chalcone derivatives under mild conditions from the easily accessible starting materials nitromethane and chalcone derivatives 2. The corresponding products were obtained in moderate yields with excellent enantioselectivities (up to 99%.

  7. Synthesis of Chiral Chalcone Derivatives Catalyzed by the Chiral Cinchona Alkaloid Squaramide

    OpenAIRE

    Dandan Xie; Ying Xie; Yan Ding; Jian Wu; Deyu Hu

    2014-01-01

    An effective method has been developed for the preparation of novel chiral chalcone derivatives under mild conditions from the easily accessible starting materials nitromethane and chalcone derivatives 2. The corresponding products were obtained in moderate yields with excellent enantioselectivities (up to 99%).

  8. Optimization of Extraction Conditions and HPTLC - UV Method for Determination of Quinine in Different Extracts of Cinchona species Bark

    Directory of Open Access Journals (Sweden)

    Dharam C. Jain

    2008-10-01

    Full Text Available A simple, precise and accurate high-performance thin-layer chromatographic method has been established for quantitative determination of quinine. Conditions were also optimized for best possible extraction of quinine via varying concentrations of diethyl amine in different solvents (n-hexane, chloroform, ethyl acetate and methanol for maximum recovery of quinine. Methanol modified with 20 % DEA found to be best for highest possible recovery of target analyte quinine. Chromatographic separation of quinine was performed on silica gel 60 F 254 HPTLC plates with ethyl acetate : diethyl amine in the proportion 88 : 12 (v/v, as mobile phase. The determination was carried out using the densitometric absorbance mode at 236 nm. Quinine response was found to be linear over the range 4–24 μg spot −1. The HPTLC method was evaluated in terms of specificity, precision, reproducibility, LOD – LOQ and robustness. Beside these parameters, number of theoretical plates and flow constant were also included as a part of validation

  9. Drug: D07153 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available 527], Cinchonine [CPD:C06528], Cinchonidine [CPD:C11379], Tannin, , Quinate [CPD:C00296] Cinchona succirubra...D07153 Crude, Drug Cinchona bark; Cinchona Quinine [CPD:C06526], Quinidine [CPD:C06..., Cinchona [TAX:43462], Rubiaceae [TAX:24966] Same as: E00257 Therapeutic category: 5100 Rubiaceae (madder f...amily) Cinchona bark Major component: Quinine [CPD:C06526] Therapeutic category of dru...gs in Japan [BR:br08301] 5 Crude drugs and Chinese medicine formulations 51 Crude drugs 510 Crude drugs 5100 Crude drugs D07153 Cinchona bark PubChem: 51091492 ...

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

    Directory of Open Access Journals (Sweden)

    Carmen Nájera

    2004-04-01

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

  11. Comparison of the Separation Performances of Cinchona Alkaloid-Based Zwitterionic Stationary Phases in the Enantioseparation of β2- and β3-Amino Acids

    Directory of Open Access Journals (Sweden)

    István Ilisz

    2014-12-01

    Full Text Available The enantiomers of twelve unusual β2- and β3-homoamino acids containing the same side-chains were separated on chiral stationary phases containing a quinine- or quinidine-based zwitterionic ion-exchanger as chiral selector. The effects of the mobile phase composition, the nature and concentration of the acid and base additives and temperature on the separations were investigated. The changes in standard enthalpy, ∆(∆H°, entropy, ∆(∆S°, and free energy, ∆(∆G°, were calculated from the linear van’t Hoff plots derived from the ln α vs. 1/T curves in the studied temperature range (10–50 °C. The values of the thermodynamic parameters depended on the nature of the selectors, the structures of the analytes, and the positions of the substituents on the analytes. A comparison of the zwitterionic stationary phases revealed that the quinidine-based ZWIX(−™ column exhibited much better selectivity for both β2- and β3-amino acids than the quinine-based ZWIX(+™ column, and the separation performances of both the ZWIX(+™ and ZWIX(−™ columns were better for β2-amino acids. The elution sequence was determined in some cases and was observed to be R < S and S < R on the ZWIX(+™ and ZWIX(−™ columns, respectively.

  12. Acylated mono-, bis- and tris- Cinchona-Based Amines Containing Ferrocene or Organic Residues: Synthesis, Structure and in Vitro Antitumor Activity on Selected Human Cancer Cell Lines

    Directory of Open Access Journals (Sweden)

    Emese Gál

    2012-02-01

    Full Text Available A series of novel functionalized mono-, bis- and tris-(S-{[(2S,4R,8R-8-ethyl-quinuclidin-2-yl](6-methoxyquinolin-4-yl}methanamines including ferrocene-containing derivatives was obtained by the reaction of the precursor amine with a variety of acylation agents. Their in vitro antitumor activity was investigated against human leukemia (HL-60, human neuroblastoma (SH-SY5Y, human hepatoma (HepG2 and human breast cancer (MCF-7 cells by the 3-(4,5-dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide (MTT-assay and the 50% inhibitory concentration (IC50 values were determined. Our data indicate that the precursor amine has no antitumor activity in vitro, but the bis-methanamines with ureido-, thioureido and amide-type linkers display attractive in vitro cytotoxicity and cytostatic effects on HL-60, HepG2, MCF-7 and SH-SY5Y cells. Besides 1H- and 13C-NMR methods the structures of the new model compounds were also studied by DFT calculations.

  13. The Arcane of Cinchona and the New Granada Expedition: the multi-dimensional mind of José Celestino Mutis (1732-1808).

    Science.gov (United States)

    Herranz, Jaime Pascual

    2014-08-01

    José Celestino Mutis y Bosio was a Spanish physician, naturalist, astronomer, priest, theologian and mathematician, and one of the icons of the Enlightment Age both in Spain and the American Continent. As the Viceroy's personal doctor, he travelled to the territory of New Granada in what is now Colombia. Mutis was the creator and first leader of the Royal Botanic Expedition of New Granada to study South American wildlife, discovering thousands of new species. He also launched several Public Health measures in the Santa Fe area, helping to introduce a vaccination campaign. Mutis was the first person to introduce Newtonian physics in the Spanish America and he established the first Observatory in the New World which is still in use. He was deeply admired and recognized as a prominent scientist by great personalities of his time including Carl von Linée and Alexander von Humboldt. PMID:24585628

  14. 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...

  15. 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

  16. Cinchona Alkaloid Derivatives Catalyzed Asymmetric Aza-Michael Addition Reaction%金鸡纳生物碱衍生物催化的不对称Aza-Michael加成反应

    Institute of Scientific and Technical Information of China (English)

    王黎明; 金瑛; 贾云宏

    2014-01-01

    将金鸡纳生物碱衍生物催化剂用于不同查尔酮和苯胺及其衍生物的不对称Aza-Michael加成反应,以65%~92%的化学产率和最高达81%e.e.的对映选择性得到R-构型加成产物.

  17. 金鸡纳-铂催化2-氧代-4-苯基丁酸乙酯的不对称加氢%Enantioselective Hydrogenation of Ethyl 2-Oxo-4-phenylbutyrate on Cinchona-Platinum Catalysts

    Institute of Scientific and Technical Information of China (English)

    夏涛; 任其龙; 吴平东

    2005-01-01

    Enantioselective hydrogenation of ethyl 2-oxo-4-phenylbutyrate to ethyl (R)-2-hydroxy-4-phenyl- bu-tyrate on Pt/γ-Al2O3 modified by 10,11-dihydrocinchonidine was studied by investigating the influences of the amount of modifier, initial concentration of reactant, pressure and temperature on conversion and enantiometric excess in a stirred autoclave and the effects of the liquid velocity, gas velocity, modifier concentration and various catalytic beds in a trickle-bed reactor. The maximum optical yields were about 50% and 60% in the two types of reactors, respectively. It was assumed that the total hydrogenation rate included the reaction rates over the unmodified and modified active sites on platinum surface and a kinetic model, which fitted the experimental data well in autoclave, was obtained. A simplified plug-flow model was proposed to describe the bed average efficiency of trickle-bed reactor.

  18. Building the world's supply of quinine: Dutch colonialism and the origins of a global pharmaceutical industry.

    Science.gov (United States)

    Goss, Andrew

    2014-03-01

    Quinine, a naturally occurring alkaloid from the Cinchona tree, was one of the first drugs produced and sold by a global pharmaceutical industry during the nineteenth century. Factories in Europe and North America dominated the manufacturing industry, and between 1890 and 1940, Cinchona plantations on Java supplied most of the bark for the quinine pharmaceutical business. At the end of the nineteenth century, the Dutch colonial state kept a hands-off approach to the Cinchona enterprises, in keeping with its liberal orientation. But the persistent low-price for bark, which led to the near ruin of the Cinchona planters, eventually pushed the colonial state to actively protect the Cinchona plantations. Colonial officials sought to stabilize the colonial Cinchona export-business by encouraging the integration of the quinine industry on a global scale. Most important was the colonial state's sponsorship in 1913 of the Quinine Agreement, establishing a set price for Cinchona bark, which created the world's first pharmaceutical cartel. In the interwar period, an alliance of Dutch government officials, planters, scientists, doctors and drug-makers, working in both the motherland and the colony, actively promoted the expansion of quinine consumption, as well as the merit of the Quinine Agreement, which they argued supplied guaranteed a steady supply of quinine, all for the wellbeing of global humanity.

  19. Colonial Agro-Industrialism : Science, Industry and the State in the Dutch Golden Alkaloid Age, 1850-1950

    OpenAIRE

    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 the Dutch empire—quinine, an antimalarial medicine. During this period, scientists, planters, traders, industrialists and state officials in the Netherlands and the former Dutch colony of the Neth...

  20. Preparation of Mesoporous SBA-16 Silica-Supported Biscinchona Alkaloid Ligand for the Asymmetric Dihydroxylation of Olefins

    Directory of Open Access Journals (Sweden)

    Shaheen M. Sarkar

    2014-01-01

    Full Text Available Optically active cinchona alkaloid was anchored onto mesoporous SBA-16 silica and the as-prepared complex was used as a heterogeneous chiral ligand of osmium tetraoxide for the asymmetric dihydroxylation of olefins. The prepared catalytic system provided 90–93% yield of vicinal diol with 92–99% enantioselectivity. The ordered mesoporous SBA-16 silica was found to be a valuable support for the cinchona alkaloid liganded osmium catalyst system which is frequently used in chemical industries and research laboratories for olefin functionalization.

  1. Organocatalytic One-Pot Asymmetric Synthesis of Thiolated Spiro-γ-lactam Oxindoles Bearing Three Stereocenters.

    Science.gov (United States)

    Huang, Xin; Liu, Miao; Pham, Kenny; Zhang, Xiaofeng; Yi, Wen-Bin; Jasinski, Jerry P; Zhang, Wei

    2016-07-01

    The first asymmetric synthesis of spiro-γ-lactam oxindoles bearing three stereocenters is reported. One-pot thiol-Michael/Mannich/lactamization reactions promoted by a recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst afford products in moderate to good yields with up to 95% ee and 6:1 dr. PMID:27258150

  2. Ion-pair formation of hydroquinine by chromatography

    NARCIS (Netherlands)

    Marchais, S.V; Vermeulen, E.S; Semple, G; Sundell, S; Wikström, H.V

    2001-01-01

    The study of hydroquinine, a Cinchona alkaloid, by analytical TLC (silica gel) in a mixture of dichloromethane and methanol (9/1, v/v) has shown that a new compound, with a higher R-F value, is formed during the migration. Its structure has been elucidated and was shown to be the hydrochloride salt

  3. Historical Review: Problematic Malaria Prophylaxis with Quinine.

    Science.gov (United States)

    Shanks, G Dennis

    2016-08-01

    Quinine, a bitter-tasting, short-acting alkaloid drug extracted from cinchona bark, was the first drug used widely for malaria chemoprophylaxis from the 19th century. Compliance was difficult to enforce even in organized groups such as the military, and its prophylaxis potential was often questioned. Severe adverse events such as blackwater fever occurred rarely, but its relationship to quinine remains uncertain. Quinine prophylaxis was often counterproductive from a public health viewpoint as it left large numbers of persons with suppressed infections producing gametocytes infective for mosquitoes. Quinine was supplied by the first global pharmaceutical cartel which discouraged competition resulting in a near monopoly of cinchona plantations on the island of Java which were closed to Allied use when the Japanese Imperial Army captured Indonesia in 1942. The problems with quinine as a chemoprophylactic drug illustrate the difficulties with medications used for prevention and the acute need for improved compounds.

  4. Effect of protonation on the conformation of cinchonidine.

    Science.gov (United States)

    Olsen, Ryan A; Borchardt, Dan; Mink, Larry; Agarwal, Arun; Mueller, Leonard J; Zaera, Francisco

    2006-12-13

    The protonation of cinchona alkaloids in solution leads to the severe restriction of their internal rotational degrees of freedom and to the locking of the molecule around a specific conformation held in place by a bridging counterion of the acid used for protonation. For HF, direct interactions were detected by NMR between the fluorine anion and not only with the acidic hydroxo group but also with non-acidic hydrogen atoms in the quinoline ring. PMID:17147361

  5. Highly enantio- and diastereoselective synthesis of β-methyl-γ- monofluoromethyl-substituted alcohols

    KAUST Repository

    Yang, Wenguo

    2011-06-07

    Enanatiopure β-methyl-γ-monofluoromethyl alcohols were prepared from the allylic alkylation between fluorobis(phenylsulfonyl)methane with Morita-Baylis-Hillman carbonates. The reaction was catalyzed by using the Cinchona alkaloid derivative, (DHQD)2AQN. The origin of the stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed stereoselectivity. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  6. A preliminary investigation of anticholinesterase activity of some Iranian medicinal plants commonly used in traditional medicine

    OpenAIRE

    Jazayeri, Seyed Behzad; Amanlou, Arash; Ghanadian, Naghmeh; Pasalar, Parvin; Amanlou, Massoud

    2014-01-01

    Background The aim of this study was to evaluate acetylcholinesterase inhibitory activity of some commonly used herbal medicine in Iran to introduce a new source for management of Alzheimer’s disease. A total of 18 aqueous-methanolic extract (1:1; v/v) from the following plants: Brassica alba, Brassica nigra, Camellia sinensis, Cinchona officinalis, Citrus aurantifolia, Citrus x aurantium, Ferula assafoetida, Humulus lupulus, Juglans regia, Juniperus sabina, Myristica fragrans, Pelargonium gr...

  7. Enantioselective Synthesis of SNAP-7941: Chiral Dihydropyrimidone Inhibitor of MCH1-R

    OpenAIRE

    Goss, Jennifer M.; Schaus, Scott E.

    2008-01-01

    An enantioselective synthesis of SNAP-7941, a potent melanin concentrating hormone receptor antagonist, was achieved using two organocatalytic methods. The first method utilized to synthesize the enantioenriched dihydropyrimidone core was the Cinchona alkaloid-catalyzed Mannich reaction of β-keto esters to acyl imines and the second was chiral phosphoric acid-catalyzed Biginelli reaction. Completion of the synthesis was accomplished via selective urea formation at the N3 position of the dihyd...

  8. Screening for antimicrobial activity of ten medicinal plants used in Colombian folkloric medicine: A possible alternative in the treatment of non-nosocomial infections

    OpenAIRE

    Ocampo Saul A; Ochoa Veronica J; Rojas Jhon J; Muñoz John F

    2006-01-01

    Abstract Background The antimicrobial activity and Minimal Inhibitory Concentration (MIC) of the extracts of Bidens pilosa L., Bixa orellana L., Cecropia peltata L., Cinchona officinalis L., Gliricidia sepium H.B. & K, Jacaranda mimosifolia D.Don, Justicia secunda Vahl., Piper pulchrum C.DC, P. paniculata L. and Spilanthes americana Hieron were evaluated against five bacteria (Staphylococcus aureus, Streptococcus β hemolític, Bacillus cereus, Pseudomonas aeruginosa, and Escherichia coli), and...

  9. Acetylphosphonate as a Surrogate of Acetate or Acetamide in Organocatalyzed Enantioselective Aldol Reactions

    Science.gov (United States)

    Guang, Jie; Guo, Qunsheng

    2012-01-01

    Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods. PMID:22650245

  10. Highly enantio- and diastereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with allyl ketones

    KAUST Repository

    Tong, Guanghu

    2013-05-17

    The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared. © 2013 American Chemical Society.

  11. Towards an asymmetric organocatalytic α-cyanation of β-ketoesters

    Science.gov (United States)

    Chowdhury, Raghunath; Schörgenhumer, Johannes; Novacek, Johanna; Waser, Mario

    2015-01-01

    This communication describes the first proof of concept for an asymmetric α-cyanation of β-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alkaloids allows obtaining the target products in good yields and with moderate enantioselectivities up to er = 76:24 under operationally simple conditions. PMID:25843983

  12. Asymmetric Aldol Reaction Catalyzed by Modularly Designed Organocatalysts

    Institute of Scientific and Technical Information of China (English)

    Sinha, Debarshi; Mandal, Tanmay; Gogoi, Sanjib; Goldman, Joshua J.; 赵从贵

    2012-01-01

    The self-assembly of the precatalyst modules, which are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for catalyzed asymmetric aldol reaction the corresponding aldol products may be obtained in mediocre diastereoselectivities (up to 79 : 21 dr). Depending on structure of the aldehyde substrates, to excellent ee values (up to 92% ee) with moderate

  13. Chiral counteranion synergistic organocatalysis under high temperature: efficient construction of optically pure spiro[cyclohexanone-oxindole] backbone.

    Science.gov (United States)

    Lan, Yu-Bao; Zhao, Hua; Liu, Zhao-Min; Liu, Guo-Gui; Tao, Jing-Chao; Wang, Xing-Wang

    2011-09-16

    The combination of a cinchona-based chiral primary amine and a BINOL-phosphoric acid has been demonstrated as a powerful and synergistic catalyst system for the double Michael addition of isatylidene malononitriles with α,β-unsaturated ketones, to provide the novel chiral spiro [cyclohexane-1,3'-indoline]-2',3-diones in high yields (88-99%) with excellent diastereo- and enantioselectivities (94:6-99:1 dr's, 95-99% ee's).

  14. FT-Raman study of quinine aqueous solutions with varying pH: 2D correlation study

    Science.gov (United States)

    Wesełucha-Birczyńska, Aleksandra

    2007-01-01

    Quinine (C 20H 24N 2O 2) is one of the best known, for its antimalarial activity, Cinchona alkaloid. In the current study 2D correlation method was applied to analyze FT-Raman spectra of quinine aqueous solutions with varying pH, which was regarded as an external perturbation. Protonation appears to be the main cause leading to the emergence of cross peaks in the synchronous and asynchronous correlation maps. One should know that protonation process is an important step associated with quinine antimalarial activity. Methoxy group manifests its presence by creation of the respective correlation peaks and seems to be significant for quinine mode of action.

  15. An Economical, Highly Efficient and Recyclable Catalyst System for Asymmetric Dihydroxylation of Olefins

    Institute of Scientific and Technical Information of China (English)

    金瑛; 孙晓莉; 姜茹; 张生勇

    2005-01-01

    A reusable cinchona alkaloid derivative ligand, which could be easily synthesized by two step transformation with cheap 3,6-dichloropyridazine and quinine as materials, was applied to homogeneous asymmetric dihydroxylation of olefins with NMO as co-oxidant in Me2CO-H20 system and the products could be extracted with Et2O from the recyclable catalyst system. 80%---93% yield and 51%-99% ee have been obtained. When trans-stilbene was chosen as the substrate for recycling experiment, 88%-92% yield and >99% ee have been obtained for ten recycles.

  16. Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

    KAUST Repository

    Liu, Chen

    2011-05-20

    A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 2011 American Chemical Society.

  17. Substrate-controlled switchable asymmetric annulations to access polyheterocyclic skeletons.

    Science.gov (United States)

    Wang, Kai-Kai; Wang, Pan; Ouyang, Qin; Du, Wei; Chen, Ying-Chun

    2016-09-25

    An unexpected domino process from Morita-Baylis-Hillman carbonates of isatins and acrylate and α-cyano-α,β-unsaturated ketones to deliver highly enantioenriched tetrahydrofuro[2',3':4,5]pyrano[2,3-b]indoles catalysed by cinchona-derived tertiary amines, involving α-regioselective cyclopropanation, ring-opening, and ring-closure cascade reactions, was disclosed. In contrast, spirooxindoles incorporating a cyclopentene motif were produced through [3+2] annulations by employing Morita-Baylis-Hillman carbonates from isatins and acrylonitrile under similar catalytic conditions. Density functional theory calculations were conducted to elucidate the novel domino process and the switchable annulation reactions. PMID:27546091

  18. Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates

    KAUST Repository

    Yang, Wenguo

    2012-08-03

    The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.

  19. Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter

    Directory of Open Access Journals (Sweden)

    Francesco Scorzelli

    2015-05-01

    Full Text Available Readily available chiral ammonium salts derived from cinchona alkaloids have proven to be effective phase transfer catalysts in the asymmetric Michael reaction of 3-substituted isoindolinones. This protocol provides a convenient method for the construction of valuable asymmetric 3,3-disubstituted isoindolinones in high yields and  moderate to good enantioselectivity. Diastereoselectivity was also investigated in the construction of contiguous tertiary and quaternary stereocenters. The use of acrolein as Michael acceptor led to an interesting tricyclic derivative, a pyrroloisoindolinone analogue, via a tandem conjugated addition/cyclization reaction.

  20. Novel chiral stationary phases based on peptoid combining a quinine/quinidine moiety through a C9-position carbamate group.

    Science.gov (United States)

    Wu, Haibo; Wang, Dongqiang; Song, Guangjun; Ke, Yanxiong; Liang, Xinmiao

    2014-04-01

    By connecting a quinine or quinidine moiety to the peptoid chain through the C9-position carbamate group, we synthesized two new chiral selectors. After immobilizing them onto 3-mercaptopropyl-modified silica gel, two novel chiral stationary phases were prepared. With neutral, acid, and basic chiral compounds as analytes, we evaluated these two stationary phases and compared their chromatographic performance with chiral columns based on quinine tert-butyl carbamate and the previous peptoid. From the resolution of neutral and basic analytes under normal-phase mode, it was found that the new stationary phases exhibited much better enantioselectivity than the quinine tert-butyl carbamate column; the peptoid moiety played an important role in enantiorecognition, which controlled the elution orders of enantiomers; the assisting role of the cinchona alkaloid moieties was observed in some separations. Under acid polar organic phase mode, it was proved that cinchona alkaloid moieties introduced excellent enantiorecognitions for chiral acid compounds; in some separations, the peptoid moiety affected enantioseparations as well. Overall, chiral moieties with specific enantioselectivity were demonstrated to improve the performance of peptoid chiral stationary phase efficiently.

  1. Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry.

    Science.gov (United States)

    Hettegger, Hubert; Kohout, Michal; Mimini, Vebi; Lindner, Wolfgang

    2014-04-11

    The synthesis and chromatographic evaluation of a series of new Cinchona derived chiral weak anion exchangers is presented. Huisgen Cu(I) mediated alkyne-azide cycloaddition, so-called click chemistry, was used as an immobilization strategy. In this way it was possible to immobilize about 90% of offered selector via 1,2,3-triazole linker, which displays a more efficient way of binding the selector to modified silica compared to common radical mediated thiol-ene addition. Problems associated with potential radical scavenging properties of chiral selectors thereby could be circumvented. The evaluation of the synthesized chiral stationary phases regarding chromatographic behavior was carried out using polar organic mode mobile phase composition and a set of representative chiral organic acids. Different loading densities revealed an optimum selector density of about 310μmol/g chiral stationary phase with respect to resolution and selectivity. A decrease of performance was observed for higher loading, indicating mutual spatial influence of selector units leading to sterical hindrance. In addition, we observed that the effect of free azide groups on retention is negligible and the overall chromatographic behavior is comparable to other Cinchona derived chiral stationary phases.

  2. Organocatalytic Asymmetric Conjugate Additions to Cyclopent-1-enecarbaldehyde: A Critical Assessment of Organocatalytic Approaches towards the Telaprevir Bicyclic Core.

    Science.gov (United States)

    Bernardi, Luca; Fochi, Mariafrancesca; Carbone, Riccardo; Martinelli, Ada; Fox, Martin E; Cobley, Christopher J; Kandagatla, Bhaskar; Oruganti, Srinivas; Dahanukar, Vilas H; Carlone, Armando

    2015-12-21

    In the context of a programme directed at the manufacture of telaprevir, eight possible approaches to its bicyclic α-amino acid core, based on organocatalytic enantioselective conjugate additions to cyclopent-1-enecarbaldehyde, were identified and preliminarily explored. Four reactions, delivering advanced intermediates en route to the target amino acid, were selected for a thorough optimisation. Three of this reactions involved iminium ion catalysis with a prolinol catalyst (addition of nitromethane, nitroacetate and acetamidomalonate) and one was based on a Cinchona-derived phase-transfer catalyst (addition of glycine imines). A careful choice of additives allowed lowering of the catalyst loading to 0.5 mol% in some cases. The preparation of intermediates that would give access to the core of telaprevir in good yields and enantioselectivities by exploiting readily available substrates and catalysts, highlights the potential of organocatalytic technology for a cost-effective preparation of pharmaceuticals. PMID:26602867

  3. Molecular-level Design of Heterogeneous Chiral Catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Gellman, Andrew John [Carnegie Mellon University; Sholl, David S. [Georgia Institute of Technology; Tysoe, Wilfred T. [University of Wisconsin - Milwaukee; Zaera, Francisco [University of California at Riverside

    2013-04-28

    ) modified by a variety of chiral templates. • Demonstrated enantioselective separation of racemic PO on chemically synthesized chiral gold nanoparticles. • Discovery of zwitterionic adsorption states of amino acids on Pd(111). • First structure determinations of adsorbed amino acids and identification of tetrameric chiral template structures. • Exploration of the enantiospecific interaction of PO and R-3-MCHO adsorption on chirally modified Cu(100), Cu(110) and Cu(111). One-to-One Interactions • Determination of cinchona orientation on Pt surfaces in situ at the solid-liquid interface using FT-IRAS. • Systematic study of the influence of solution properties on the adsorption of modified cinchonas alkaloids onto Pt surfaces. • Correlation of cinchona adsorption with catalytic activity, as affected by concentration, the nature of the solvent, and dissolved gases in the liquid phase. • Measurement of enantioselective chemisorption on 1-(1-naphthyl) ethylamine (NEA) modified Pt(111) and Pd(111) surfaces. • Imaging of chiral docking complexes between NEA and methyl pyruvate on Pd(111). Chiral Catalyst Synthesis • Anchoring of cinchona alkaloid to surfaces • Synthesis of chiral Au nanoparticles and demonstration of their enantiospecific interactions with R- and S-PO. • Elucidation of the driving forces for chiral imprinting of Cu(100) by L- and D-lysine to form Cu(3,1,17)R&S facets.

  4. Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis

    Science.gov (United States)

    Bencivenni, Giorgio; Galzerano, Patrizia; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo

    2010-01-01

    In spite of the many catalytic methodologies available for the asymmetric functionalization of carbonyl compounds at their α and β positions, little progress has been achieved in the enantioselective carbon–carbon bond formation γ to a carbonyl group. Here, we show that primary amine catalysis provides an efficient way to address this synthetic issue, promoting vinylogous nucleophilicity upon selective activation of unmodified cyclic α,β-unsaturated ketones. Specifically, we document the development of the unprecedented direct and vinylogous Michael addition of β-substituted cyclohexenone derivatives to nitroalkenes proceeding under dienamine catalysis. Besides enforcing high levels of diastereo- and enantioselectivity, chiral primary amine catalysts derived from natural cinchona alkaloids ensure complete γ-site selectivity: The resulting, highly functionalized vinylogous Michael adducts, having two stereocenters at the γ and δ positions, are synthesized with very high fidelity. Finally, we describe the extension of the dienamine catalysis-induced vinylogous nucleophilicity to the asymmetric γ-amination of cyclohexene carbaldehyde. PMID:20566884

  5. Monitoring surface processes during heterogeneous asymmetric hydrogenation of ketones on a chirally modified platinum catalyst by operando spectroscopy.

    Science.gov (United States)

    Meemken, Fabian; Hungerbühler, Konrad; Baiker, Alfons

    2014-08-11

    Surface processes occurring at the catalytic chiral surface of a cinchona-modified Pt catalyst during the asymmetric hydrogenation of activated ketones have been monitored for the first time using operando ATR-IR spectroscopy. Fundamental information about this catalytic system could be gained, including the chiral modification process of the catalyst, the surface interaction of reactant ketone with preadsorbed chiral modifier, the role of hydrogen as well as the influence of the product enantiomers in the catalytic cycle. The formation of a diastereomeric transient surface complex between ketone and chiral modifier was found to be related to the ketone consumption. Among the studied activated ketones, a correlation between stereoselection and the strength of the intermolecular hydrogen bond was identified. Dissociated hydrogen from the catalytic surface is found to play a crucial role in the formation of the diastereomeric surface complex. PMID:24777839

  6. Asymmetric Desymmetrization via Metal-Free C-F Bond Activation: Synthesis of 3,5-Diaryl-5-fluoromethyloxazolidin-2-ones with Quaternary Carbon Centers.

    Science.gov (United States)

    Tanaka, Junki; Suzuki, Satoru; Tokunaga, Etsuko; Haufe, Günter; Shibata, Norio

    2016-08-01

    We disclose the first asymmetric activation of a non-activated aliphatic C-F bond in which a conceptually new desymmetrization of 1,3-difluorides by silicon-induced selective C-F bond scission is a key step. The combination of a cinchona alkaloid based chiral ammonium bifluoride catalyst and N,O-bis(trimethylsilyl)acetoamide (BSA) as the silicon reagent enabled the efficient catalytic cycle of asymmetric Csp3 -F bond cleavage under mild conditions with high enantioselectivities. The ortho effect of the aryl group at the prostereogenic center is remarkable. This concept was applied for the asymmetric synthesis of promising agrochemical compounds, 3,5-diaryl-5-fluoromethyloxazolidin-2-ones bearing a quaternary carbon center.

  7. Some Topics in Relation to José Celestino Mutis and Medicine

    Directory of Open Access Journals (Sweden)

    Leonardo Palacios Sánchez

    2008-07-01

    Full Text Available José Celestino Mutis showed different interestareas of study and worked in multipleknowledge fields: mathematics, mineralogy, astronomy,zoology and botanic, the one in whichis best known. However, he was a medical doctor,whit profound an up to date knowledge. Hestudied at Sevilla University, and in the RoyalCollege of Cadiz. He arrived to the “NuevoReino de Granada” as personal medical doctorof the the viceroy Pedro Messía de la Cerda andduring 47 years, period of time he lived there,he always exercised his profession. We showeda special interest in the study of cinchona andthe only work he published was El Arcano dela quina. He advised in public health manyviceroys and he contributed in different fieldsbut particularly in the prevention of smallpoxby inoculation. He played a decisive role in thereopening of the medical school of the ColegioMayor de Nuestra Señora del Rosario. Someof his achievements justifies the appellative“Father of the Medicine in Colombia”.

  8. Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations.

    Science.gov (United States)

    Chen, Shi; Ibrahim, Ahmad A; Peraino, Nicholas J; Nalla, Divya; Mondal, Mukulesh; Van Raaphorst, Maxwell; Kerrigan, Nessan J

    2016-09-01

    In this article we describe extensive studies of the catalytic asymmetric heterodimerization of ketenes to give ketene heterodimer β-lactones. The optimal catalytic system was determined to be a cinchona alkaloid derivative (TMS-quinine or Me-quinidine). The desired ketene heterodimer β-lactones were obtained in good to excellent yields (up to 90%), with excellent levels of enantioselectivity (≥90% ee for 33 Z and E isomer examples), good to excellent (Z)-olefin isomer selectivity (≥90:10 for 20 examples), and excellent regioselectivity (only one regioisomer formed). Full details of catalyst development studies, catalyst loading investigations, substrate scope exploration, protocol innovations (including double in situ ketene generation for 7 examples), and an application to a cinnabaramide A intermediate are described. The addition of lithium perchlorate (1-2 equiv) as an additive to the alkaloid catalyst system was found to favor formation of the E isomer of the ketene heterodimer. Ten examples were formed with moderate to excellent (E)-olefin isomer selectivity (74:25 to 97:3) and with excellent enantioselectivity (84-98% ee). PMID:27490092

  9. Analysis on the Application and Development of Antimalarials Drugs%抗疟药物的应用与发展

    Institute of Scientific and Technical Information of China (English)

    张楠

    2016-01-01

    人类在抗疟药物的应用过程中,先后经历了蚊帐、纱窗、巫术、中草药等传统办法,由金鸡纳树皮的疗效促使了奎宁、氯喹的产生,以及DDT杀虫剂和青蒿素类药物的使用,上述治疗手段和方法都对控制疟疾的传播扩散发挥了重要作用。本文通过回顾这些抗疟药物应用历程的同时,以期展望该领域的发展前景和未来趋势。%In the history, human used several ways, such as mosquito nets, screens, witchcraft, Chinese herbal medicine and other traditional ways, and due to the curative effect of cinchona bark, human find quinine and chloroquine, later, the pesticide DDT and arte-misinin drugs also can be found.All of them played an important role to control the spread of malaria.This paper is overviewed how many treatments and methods which by human used and found, and its development is also prospected.

  10. New insight into the stereoselective interactions of quinine and quinidine, with bovine serum albumin.

    Science.gov (United States)

    Liu, Yan; Chen, Mingmao; Wang, Shuaihua; Lin, Jingjing; Cai, Lizhen; Song, Ling

    2014-05-01

    Quinine (QN) and quinidine (QD), the chief quinoline alkaloids of various species of cinchona bark, are stereoisomers to each other. In this study, a series of appropriate and efficient methods have been applied to compare the binding modes of QN and QD with bovine serum albumin (BSA). The isothermal titration calorimetry and room temperature phosphorescence results show that both QN and QD can interact with BSA at one binding site to form drug-protein complexes, mainly through enthalpic driving force with the binding affinity order: QN > QD. The fluorescence resonance energy transfer and time-resolved fluorescence spectroscopy exhibits that QN has a larger energy transfer and more intensified binding capacity for BSA than QD. Data of dynamic light scattering reveal that the aggregate state of BSA is changed during this binding process, and the particle size distribution of QN-BSA bioconjugate is larger than that of QD. Nuclear magnetic resonance analysis indicates that aromatic protons make more contribution during ligand-protein complexation than that of aliphatic protons. The circular dichroism spectra exhibit different degrees of changes in BSA secondary structures in the presence of QN and QD, respectively.

  11. Electrochemical studies of quinine in surfactant media using hanging mercury drop electrode: a cyclic voltammetric study.

    Science.gov (United States)

    Dar, Riyaz Ahmad; Brahman, Pradeep Kumar; Tiwari, Sweety; Pitre, Krishna Sadashiv

    2012-10-01

    The electrochemical behavior of quinine was investigated by cyclic voltammetry (CV) and square wave voltammetry (SWV) using surfactant. The reduction peak current of quinine increases remarkably in presence of 1% CTAB. Its electrochemical behavior is quasi-reversible in the Britton-Robinson buffers of pH 10.38 by exhibiting the well-defined single cathodic and anodic waves and the ratio of I(p)(a)/I(p)(c) approaching one at the scan rate of 500 mVs(-1). On the basis of CV, SWV and Coulometry, electrochemical reduction mechanism of quinine has been proposed which has shown that protonation occurs on the nitrogen of the quinoline moiety. Linearity was obtained when the peak currents (I(p)) were plotted against concentrations of quinine in the range of 30.0-230.0 ng mL(-1) with a detection limit of 0.132 ng mL(-1) in SWV and 90.0-630.0 ng mL(-1) with a detection limit of 0.238 ng mL(-1) in DPV. Fast and sensitive SWV has been applied for the quantitative analysis of quinine in bark of Cinchona sp. and in soft drinks and a good recovery was obtained. The accuracy and precision of the method are determined and validated statistically. No interferences from other food additives were observed. The relative standard deviation for intraday and interday assay was 0.89 and 0.73% (n=3) respectively.

  12. Synthesis of triazol derivatives of lupeol with potential antimalarial activity

    Directory of Open Access Journals (Sweden)

    Tatiane Freitas Borgati

    2012-06-01

    Full Text Available The goal of this project is synthesize and characterization of derivatives of lupeol and evaluated antimalarial activity. Historically, plants are important source of antimalarial medicines, highlighting quinine (1 (Figure 1, an important      alkaloid from the Cinchona calisaya bark. This compound was an important model for cloroquine  synthesis, a drug that was widely used in malaria treatment. In addition, one of the principal medicines used today is artemisinine, isolated from the Chinese plant Artemisia annua L (2 (Figure 1, and their semi synthetic derivatives (artesunate, artemeter, arteter. However, the malaria parasite has already shown resistance    to most of these current drugs and  the search for new candidates is essential. Lupeol (3 (Figura 1 is a compound that occurs in many plant species and discloses antimalarial, antiinflamatoryl and antitumoral activities. Considering its potential as a lead antimalarial molecule, we focused our work in the synthesis of new lupeol derivatives with increased antimalarial activity(scheme 1.

  13. Amazonian Plant Natural Products: Perspectives for Discovery of New Antimalarial Drug Leads

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    Lucio H. Freitas-Junior

    2013-08-01

    Full Text Available Plasmodium falciparum and P. vivax malaria parasites are now resistant, or showing signs of resistance, to most drugs used in therapy. Novel chemical entities that exhibit new mechanisms of antiplasmodial action are needed. New antimalarials that block transmission of Plasmodium spp. from humans to Anopheles mosquito vectors are key to malaria eradication efforts. Although P. vivax causes a considerable number of malaria cases, its importance has for long been neglected. Vivax malaria can cause severe manifestations and death; hence there is a need for P. vivax-directed research. Plants used in traditional medicine, namely Artemisia annua and Cinchona spp. are the sources of the antimalarial natural products artemisinin and quinine, respectively. Based on these compounds, semi-synthetic artemisinin-derivatives and synthetic quinoline antimalarials have been developed and are the most important drugs in the current therapeutic arsenal for combating malaria. In the Amazon region, where P. vivax predominates, there is a local tradition of using plant-derived preparations to treat malaria. Here, we review the current P. falciparum and P. vivax drug-sensitivity assays, focusing on challenges and perspectives of drug discovery for P. vivax, including tests against hypnozoites. We also present the latest findings of our group and others on the antiplasmodial and antimalarial chemical components from Amazonian plants that may be potential drug leads against malaria.

  14. [Historical notes on the therapy of depression].

    Science.gov (United States)

    Haenel, T

    1986-11-22

    Melancholy originally had another meaning from the present one. Only since the last century has melancholy taken on the meaning of severe depression. The Arabs were the first to introduce special wards for the mentally ill in their hospitals in the 8th and 9th centuries. In the West, mental wards in general hospitals have been known since the 13th century only. In the Renaissance dietary measures played an important part in the treatment of depression. Lean meat, fresh eggs, freshwater fish and particularly grapes were recommended. In the 17th and 18th centuries music therapy against depression came back into favour after being used in ancient times. In the 19th century opium was recommended and held its ground well into the middle of our century. Various methods and drugs were recommended and used for the therapy of depression in the 19th century, such as baths and massage, ferrous iodide, arsenic, ergot, strophantin, and cinchona. Actual antidepressants have been known only for approximately 30 years. The classic papers concerning therapy with lithium salts date back to the years 1948/49. It is a little known fact, however, that lithium salts had been used as prophylactic treatment against periodic depression 50 years earlier. PMID:3541174

  15. The Stereoselective Epoxidation by a New Type of Soluble Polymer-Supported Catalysts

    Institute of Scientific and Technical Information of China (English)

    Wang Yongmei; Wang Xin; Liu Juyan

    2004-01-01

    As the phase transfer catalyst (PTC) is one of most important catalysts in organic synthesis. Here, we represent initial results of a research program aimed at the rational design of a variety of new two centers, soluble polyethylene glycol (PEG) supported catalysts based on the cinchona alkaloid system and their application in asymmetric expoxidation process.Table 1 and Table 2 summarized the results of epoxidation of substituted chalcone As shown in Table 1 and Table 2, chalcone derivatives as reactive olefins afforded the corresponding epoxided with modest to good enantiomeric excesses. In contrast, a definite trend to higher ee value is displayed by solvent effect. It was found that enantioselectivity becomes higher with the polarity increases(Table 1, Table 2). Changing catalyst 1 to catalyst 2, ee value was increased (entry 6 in Table 1) as well. Compared with Me, NO2 groups, substitution on the aromatic ring of the enone carbonyl function by OMe group increased the enantioselectivity(entry 3 in Table 1 and entry 3' in Table 2).

  16. Separation of drug stereoisomers by the formation of. beta. -cyclodextrin inclusion complexes

    Energy Technology Data Exchange (ETDEWEB)

    Armstrong, D.W.; Ward, T.J.; Armstrong, R.D.; Beesley, T.E.

    1986-05-30

    For many drugs, only racemic mixtures are available for clinical use. Because different stereoisomers of drugs often cause different physiological responses, the use of pure isomers could elicit more exact therapeutic effects. Differential complexation of a variety of drug stereoisomers by immobilized ..beta..-cyclodextrin was investigated. Chiral recognition and racemic resolution were observed with a number of compounds from such clinically useful classes as ..beta..-blockers, calcium-channel blockers, sedative hypnotics, antihistamines, anticonvulsants, diuretics, and synthetic opiates. Separation of the diastereomers of the cardioactive and antimalarial cinchona alkaloids and of two antiestrogens was demonstrated as well. Three dimensional projections of ..beta..-cyclodextrin complexes of propanol, which is resolved by this technique, and warfarin, which is not, are compared. These studies have improved the understanding and application of the chiral interactions of ..beta..-cyclodextrin, and they have demonstrated a means to measure optical purity and to isolate or produce pure enantiomers of drugs. In addition, this highly specific technique could also be used in the pharmacological evaluation of enantiometric drugs. 27 references, 3 figures, 2 tables.

  17. Unexpectedly High Beta-Diversity of Root-Associated Fungal Communities in the Bolivian Andes.

    Science.gov (United States)

    Barnes, Christopher J; Maldonado, Carla; Frøslev, Tobias G; Antonelli, Alexandre; Rønsted, Nina

    2016-01-01

    Bolivia is one of the most biologically diverse countries on the planet. Between the Andes and the Amazon drainage basin spans the Yungas, a vast forested region shown to be extremely species rich in macro-organisms. However, it remains unclear whether this high diversity is also reflected in microbial diversity. Here we assess the genetic, taxonomic and functional diversity of root-associated fungi surrounding Cinchona calisaya trees, a typical element of the intermediate altitudes of the Bolivian Yungas. We determine the relative effects of edaphic properties, climate, and geography in regulating fungal community assembly. We show that α-diversity for these fungal communities was similar to temperate and arid ecosystems, averaging 90.1 operational taxonomic units (OTUs) per sample, with reads predominantly assigned to the Ascomycota phylum and with a saprotrophic lifestyle. ß-diversity was calculated as the distance-decay rate, and in contrast to α-diversity, was exceptionally high with a rate of -0.407. Soil properties (pH and P) principally regulated fungal community assembly in an analogous manner to temperate environments, with pH and phosphorus explaining 7.8 and 7.2% of community variation respectively. Surprisingly, altitude does not influence community formation, and there is limited evidence that climate (precipitation and temperature) play a role. Our results suggest that sampling should be performed over a wide geographical and environmental range in order to capture the full root-associated fungal diversity in subtropical regions. This study sheds further light on the diversity and distribution of the world's "hidden biodiversity." PMID:27630629

  18. Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

    Directory of Open Access Journals (Sweden)

    Pierre Vogel

    2016-08-01

    Full Text Available Catalysis fulfills the promise that high-yielding chemical transformations will require little energy and produce no toxic waste. This message is carried by the study of the evolution of molecular catalysis of some of the most important reactions in organic chemistry. After reviewing the conceptual underpinnings of catalysis, we discuss the applications of different catalysts according to the mechanism of the reactions that they catalyze, including acyl group transfers, nucleophilic additions and substitutions, and C–C bond forming reactions that employ umpolung by nucleophilic additions to C=O and C=C double bonds. We highlight the utility of a broad range of organocatalysts other than compounds based on proline, the cinchona alkaloids and binaphthyls, which have been abundantly reviewed elsewhere. The focus is on organocatalysts, although a few examples employing metal complexes and enzymes are also included due to their significance. Classical Brønsted acids have evolved into electrophilic hands, the fingers of which are hydrogen donors (like enzymes or other electrophilic moieties. Classical Lewis base catalysts have evolved into tridimensional, chiral nucleophiles that are N- (e.g., tertiary amines, P- (e.g., tertiary phosphines and C-nucleophiles (e.g., N-heterocyclic carbenes. Many efficient organocatalysts bear electrophilic and nucleophilic moieties that interact simultaneously or not with both the electrophilic and nucleophilic reactants. A detailed understanding of the reaction mechanisms permits the design of better catalysts. Their construction represents a molecular science in itself, suggesting that sooner or later chemists will not only imitate Nature but be able to catalyze a much wider range of reactions with high chemo-, regio-, stereo- and enantioselectivity. Man-made organocatalysts are much smaller, cheaper and more stable than enzymes.

  19. Transits of Venus and Colonial India

    Science.gov (United States)

    Kochhar, Rajesh

    2012-09-01

    Astronomical expeditions during the colonial period had a political and national significance also. Measuring the earth and mapping the sky were activities worthy of powerful and power- seeking nations. Such was the sanctity of global astronomical activity that many other agendas could be hidden under it. An early astronomy-related expedition turned out to be extremely beneficial, to botany. The expedition sent by the French Government in 1735 to South America under the leadership of Charles Marie de la Condamine (1701--1774) ostensibly for the measurement of an arc of the meridian at Quito in Ecuador surreptitiously collected data that enabled Linnaeus to describe the genus cinchona in 1742. When the pair of transits of Venus occurred in 1761 and 1769, France and England were engaged in a bitter rivalry for control of India. The observation of the transits became a part of the rivalry. A telescope presented by the British to a South Indian King as a decorative toy was borrowed back for actual use. Scientifically the transit observations were a wash out, but the exercise introduced Europe to details of living Indian tradition of eclipse calculations. More significantly, it led to the institutionalization of modern astronomy in India under the auspices of the English East India Company (1787). The transits of Venus of 1874 and 1882 were important not so much for the study of the events as for initiating systematic photography of the Sun. By this, Britain owned most of the world's sunshine, and was expected to help European solar physicists get data from its vast Empire on a regular basis. This and the then genuinely held belief that a study of the sun would help predict failure of monsoons led to the institutionalization of solar physics studies in India (1899). Of course, when the solar physicists learnt that solar activity did not quite determine rainfall in India, they forgot to inform the Government.

  20. Unexpectedly High Beta-Diversity of Root-Associated Fungal Communities in the Bolivian Andes

    Science.gov (United States)

    Barnes, Christopher J.; Maldonado, Carla; Frøslev, Tobias G.; Antonelli, Alexandre; Rønsted, Nina

    2016-01-01

    Bolivia is one of the most biologically diverse countries on the planet. Between the Andes and the Amazon drainage basin spans the Yungas, a vast forested region shown to be extremely species rich in macro-organisms. However, it remains unclear whether this high diversity is also reflected in microbial diversity. Here we assess the genetic, taxonomic and functional diversity of root-associated fungi surrounding Cinchona calisaya trees, a typical element of the intermediate altitudes of the Bolivian Yungas. We determine the relative effects of edaphic properties, climate, and geography in regulating fungal community assembly. We show that α-diversity for these fungal communities was similar to temperate and arid ecosystems, averaging 90.1 operational taxonomic units (OTUs) per sample, with reads predominantly assigned to the Ascomycota phylum and with a saprotrophic lifestyle. ß-diversity was calculated as the distance-decay rate, and in contrast to α-diversity, was exceptionally high with a rate of −0.407. Soil properties (pH and P) principally regulated fungal community assembly in an analogous manner to temperate environments, with pH and phosphorus explaining 7.8 and 7.2% of community variation respectively. Surprisingly, altitude does not influence community formation, and there is limited evidence that climate (precipitation and temperature) play a role. Our results suggest that sampling should be performed over a wide geographical and environmental range in order to capture the full root-associated fungal diversity in subtropical regions. This study sheds further light on the diversity and distribution of the world's “hidden biodiversity.” PMID:27630629

  1. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions

    Directory of Open Access Journals (Sweden)

    Wright Colin W

    2011-03-01

    Full Text Available Abstract Background In traditional medicine whole plants or mixtures of plants are used rather than isolated compounds. There is evidence that crude plant extracts often have greater in vitro or/and in vivo antiplasmodial activity than isolated constituents at an equivalent dose. The aim of this paper is to review positive interactions between components of whole plant extracts, which may explain this. Methods Narrative review. Results There is evidence for several different types of positive interactions between different components of medicinal plants used in the treatment of malaria. Pharmacodynamic synergy has been demonstrated between the Cinchona alkaloids and between various plant extracts traditionally combined. Pharmacokinetic interactions occur, for example between constituents of Artemisia annua tea so that its artemisinin is more rapidly absorbed than the pure drug. Some plant extracts may have an immunomodulatory effect as well as a direct antiplasmodial effect. Several extracts contain multidrug resistance inhibitors, although none of these has been tested clinically in malaria. Some plant constituents are added mainly to attenuate the side-effects of others, for example ginger to prevent nausea. Conclusions More clinical research is needed on all types of interaction between plant constituents. This could include clinical trials of combinations of pure compounds (such as artemisinin + curcumin + piperine and of combinations of herbal remedies (such as Artemisia annua leaves + Curcuma longa root + Piper nigum seeds. The former may enhance the activity of existing pharmaceutical preparations, and the latter may improve the effectiveness of existing herbal remedies for use in remote areas where modern drugs are unavailable.

  2. Organocatalytic Asymmetric Michael Additions%有机催化不对称Michael加成反应

    Institute of Scientific and Technical Information of China (English)

    李宁; 郗国宏; 吴秋华; 刘伟华; 马晶军; 王春

    2009-01-01

    有机催化的不对称合成反应是目前研究最为活跃的领域之一.不对称Michael加成反应是合成众多重要的手性合成子和药物中间体的有效手段.目前报道的催化Michael加成反应的有机催化剂主要有脯氨酸及其衍生物、手性咪唑啉酮、手性(硫)脲、金鸡纳碱衍生物等.对各类有机催化剂在有机催化不对称Michael加成反应中的应用,以及不对称诱导反应的机理、催化剂分子结构及反应条件对其催化活性和不对称诱导作用的影响进行了评述.%Organocatalytic asymmetric reaction is an increasingly active area in organic synthesis. The asymmetric Michael addition provides a rapid access to versatile important chiral building blocks and intermediates for the synthesis of bioactive agrochemicals and pharmaceutical compounds. The reported organocatalysts for asymmetric Michael additions include proline and its derivatives, chiral imidazolidinone derivatives, chiral (thio) urea, cinchona alkaloids and so on. The applications of various organocatalysts to asymmetric Michael additions are reviewed in this paper. The reaction mechanism, catalytic activity and the asymmetric induction influenced by the structure of organocatalysts and the reaction condition are also discussed.

  3. Medicinal plants, human health and biodiversity: a broad review.

    Science.gov (United States)

    Sen, Tuhinadri; Samanta, Samir Kumar

    2015-01-01

    Biodiversity contributes significantly towards human livelihood and development and thus plays a predominant role in the well being of the global population. According to WHO reports, around 80 % of the global population still relies on botanical drugs; today several medicines owe their origin to medicinal plants. Natural substances have long served as sources of therapeutic drugs, where drugs including digitalis (from foxglove), ergotamine (from contaminated rye), quinine (from cinchona), and salicylates (willow bark) can be cited as some classical examples.Drug discovery from natural sources involve a multifaceted approach combining botanical, phytochemical, biological, and molecular techniques. Accordingly, medicinal-plant-based drug discovery still remains an important area, hitherto unexplored, where a systematic search may definitely provide important leads against various pharmacological targets.Ironically, the potential benefits of plant-based medicines have led to unscientific exploitation of the natural resources, a phenomenon that is being observed globally. This decline in biodiversity is largely the result of the rise in the global population, rapid and sometimes unplanned industrialization, indiscriminate deforestation, overexploitation of natural resources, pollution, and finally global climate change.Therefore, it is of utmost importance that plant biodiversity be preserved, to provide future structural diversity and lead compounds for the sustainable development of human civilization at large. This becomes even more important for developing nations, where well-planned bioprospecting coupled with nondestructive commercialization could help in the conservation of biodiversity, ultimately benefiting mankind in the long run.Based on these findings, the present review is an attempt to update our knowledge about the diverse therapeutic application of different plant products against various pharmacological targets including cancer, human brain

  4. Five prevalent antiprotozoal herbal drugs

    Directory of Open Access Journals (Sweden)

    Mohammad Azadbakht1

    2008-01-01

    Full Text Available , (Received 21 Jun, 2008 ; Accepted 12 Nov, 2008 AbstractAccording to the statistics provided by the World Health Organization (WHO, about 80% of the world population nowadays uses herbal drugs for treatment of diseases. Natural products obtained from medicinal plants, serve as a great source for drug production and are the main basis of new drug compounds. Unicellular organisms (Protozoa are the cause of deaths and spread of diseases in various societies, especially in developing countries. There are anti-malaria herbal dugs produced from various medicinal plants, some of which are used for treatment of the disease and some under study. The first anti-malaria drug was quinine, produced from bark of the Cinchona tree. Recently, the drug artemisinin has been introduced by Chinese scientists for the treatment of malaria and is currently used extensively. Coetaneous leishmaniosis (salak is one of the endemic diseases in most parts of Iran. Common drugs used against leishmaniosis (such as glucantim, have severe side-effects and in 10 to 25% of cases, there is a recurrence of the disease. Emetine is one of the drugs obtained from a root of the plant Ipecac, which is used for treatment of the disease sub-cutaneously. Giardiasis is an acute protozoan infection usually with no clinical symptoms, however, may appear as acute or chronic diarrhea. According to the announcement of WHO, more than 2/3 of the world’s population is infected with intestinal parasites and the prevalence of giardia is higher than other intestinal parasites. Herbal drugs, such as wild garlic, eucalyptus and thyme, are some of the major plants which can annihilate the giarda cysts. Annually, 75000 to 100000 people die of amebiasis (dysentery worldwide. Due to the motility of the organism, it causes sever pathological changes and sometimes colon ulcers, and if entered into the blood stream, it may appear as liver or brain abscess. Medicinal plants such as ipecac, mango, and papaya

  5. [Alexandre Yersin (1863-1943), explorer and a founding scientist of the Pasteur Institutes].

    Science.gov (United States)

    Milleliri, J M

    2014-01-01

    2013 was the year to celebrate Yersin: the 150th anniversary of his birth and the 70th anniversary of his death. Beyond the images usually attached to the memory of this doctor who discovered the bubonic plague bacillus (in Hong Kong in 1894), the author seeks to introduce Yersin, the man, as an explorer curious about his environment rather than a scientist concerned with honors and public recognition. Alexandre Yersin is an atypical figure in the universe of Pasteur, his collaborators, students, and followers. Although he began his career working with Louis Pasteur following the development of the vaccine against rabies, in 1885, the call of the sea led him to quit the laboratory on rue Ulm to, he said, "explore new lands". He worked for the Messageries maritimes merchant shipping company. In Saigon, he met Albert Calmette, who convinced him to join the newly created Colonial Army Medical Corps. In 1892 in Nha-Trang, Yersin set up a bacteriology laboratory in a straw hut; it subsequently became the first Pasteur Institute in Indochina, the starting point of a network of research laboratories. During the bubonic plague epidemic that raged in Hong Kong, Yersin succeeded in isolating its causal agent, surprising even himself by the ease with which he did so. He was 30 years old then, but what could have been the start of a prestigious career, crowned with honors, was spent instead at the service of the local populations. His exploration of the Vietnam highlands gave Yersin the occasion to cultivate and reveal a prodigious eclecticism and his profound humanism. He led three explorations in unknown regions of Annam and contributed to the development of this country by his social, educational, medical, and economic approach, entirely dedicated to aiding the indigenous populations. Yersin never left Vietnam again. He worked as an astronomer and agronomist (introducing the cultivation of cinchona (source of quinine) and rubber trees in the country) - always close to the

  6. Screening for antimicrobial activity of ten medicinal plants used in Colombian folkloric medicine: A possible alternative in the treatment of non-nosocomial infections

    Directory of Open Access Journals (Sweden)

    Ocampo Saul A

    2006-02-01

    Full Text Available Abstract Background The antimicrobial activity and Minimal Inhibitory Concentration (MIC of the extracts of Bidens pilosa L., Bixa orellana L., Cecropia peltata L., Cinchona officinalis L., Gliricidia sepium H.B. & K, Jacaranda mimosifolia D.Don, Justicia secunda Vahl., Piper pulchrum C.DC, P. paniculata L. and Spilanthes americana Hieron were evaluated against five bacteria (Staphylococcus aureus, Streptococcus β hemolític, Bacillus cereus, Pseudomonas aeruginosa, and Escherichia coli, and one yeast (Candida albicans. These plants are used in Colombian folk medicine to treat infections of microbial origin. Methods Plants were collected by farmers and traditional healers. The ethanol, hexane and water extracts were obtained by standard methods. The antimicrobial activity was found by using a modified agar well diffusion method. All microorganisms were obtained from the American Type Culture Collection (ATCC. MIC was determined in the plant extracts that showed some efficacy against the tested microorganisms. Gentamycin sulfate (1.0 μg/ml, clindamycin (0.3 μg/ml and nystatin (1.0 μg/ml were used as positive controls. Results The water extracts of Bidens pilosa L., Jacaranda mimosifolia D.Don, and Piper pulchrum C.DC showed a higher activity against Bacillus cereus and Escherichia coli than gentamycin sulfate. Similarly, the ethanol extracts of all species were active against Staphylococcus aureus except for Justicia secunda. Furthermore, Bixa orellana L, Justicia secunda Vahl. and Piper pulchrum C.DC presented the lowest MICs against Escherichia coli (0.8, 0.6 and 0.6 μg/ml, respectively compared to gentamycin sulfate (0.9 8g/ml. Likewise, Justicia secunda and Piper pulchrum C.DC showed an analogous MIC against Candida albicans (0.5 and 0.6 μg/ml, respectively compared to nystatin (0.6 μg/ml. Bixa orellana L, exhibited a better MIC against Bacillus cereus (0.2 μg/ml than gentamycin sulfate (0.5 μg/ml. Conclusion This in vitro study

  7. [Alexandre Yersin (1863-1943), explorer and a founding scientist of the Pasteur Institutes].

    Science.gov (United States)

    Milleliri, J M

    2014-01-01

    2013 was the year to celebrate Yersin: the 150th anniversary of his birth and the 70th anniversary of his death. Beyond the images usually attached to the memory of this doctor who discovered the bubonic plague bacillus (in Hong Kong in 1894), the author seeks to introduce Yersin, the man, as an explorer curious about his environment rather than a scientist concerned with honors and public recognition. Alexandre Yersin is an atypical figure in the universe of Pasteur, his collaborators, students, and followers. Although he began his career working with Louis Pasteur following the development of the vaccine against rabies, in 1885, the call of the sea led him to quit the laboratory on rue Ulm to, he said, "explore new lands". He worked for the Messageries maritimes merchant shipping company. In Saigon, he met Albert Calmette, who convinced him to join the newly created Colonial Army Medical Corps. In 1892 in Nha-Trang, Yersin set up a bacteriology laboratory in a straw hut; it subsequently became the first Pasteur Institute in Indochina, the starting point of a network of research laboratories. During the bubonic plague epidemic that raged in Hong Kong, Yersin succeeded in isolating its causal agent, surprising even himself by the ease with which he did so. He was 30 years old then, but what could have been the start of a prestigious career, crowned with honors, was spent instead at the service of the local populations. His exploration of the Vietnam highlands gave Yersin the occasion to cultivate and reveal a prodigious eclecticism and his profound humanism. He led three explorations in unknown regions of Annam and contributed to the development of this country by his social, educational, medical, and economic approach, entirely dedicated to aiding the indigenous populations. Yersin never left Vietnam again. He worked as an astronomer and agronomist (introducing the cultivation of cinchona (source of quinine) and rubber trees in the country) - always close to the

  8. Large-scale deforestation for plantation agriculture in the hill country of Sri Lanka and its impacts

    Science.gov (United States)

    Wickramagamage, P.

    1998-10-01

    The forest cover in the hill country river catchment areas of Sri Lanka has been reduced to isolated patches on hilltops and a handful of reserves above the 1524 m (5000 ft) contour. Most of the land that was under forest cover at the turn of the nineteenth century is now covered with plantation crops. The districts of Kandy, Matale, Nuwara Eliya, Badulla, Ratnapura and Kegalle are the main hill country plantation areas. Within a period of less than half a century most of the forests in the hill country were cleared for plantation crops. Shifting cultivation was responsible for deforestation in the drier parts of the hill country. At the time of the British conquest of the hill country, the population of the whole island was not more than 3/4 to 1 million and they had settled in isolated villages at elevations below 1066 m. Subsistence agriculture was the main occupation of this predominantly rural population.During the first phase (1830-1880) of the plantation industry, large tracts of mostly forest land were cleared for coffee cultivation. By 1878, the extent of the coffee plantations reached its maximum of 111 336 ha most of which was situated in the wet zone hill country. The second phase of plantation agriculture began as the coffee industry was completely wiped out by a leaf disease. Most of the abandoned coffee plantations and the remaining forests were converted to tea, rubber and cinchona estates. The first two crops managed to survive price fluctuations in the world market, while the latter collapsed because of over production.During the period of large-scale deforestation in the hill country, the climate also underwent changes as exemplified by rainfall and temperature trends. However, these trends are not uniform everywhere in the plantation areas of the hill country. The temperature has risen a few degrees over a period of about a century and quarter in the hill country stations, while rainfall has declined significantly at some stations. These changes

  9. Utilization of N-X bonds in the synthesis of N-heterocycles.

    Science.gov (United States)

    Minakata, Satoshi

    2009-08-18

    -deficient olefins in the presence of a phase transfer catalyst to give the corresponding aziridines. We also used this method to synthesize asymmetric aziridines using quaternary cinchona alkaloid catalysts. We also developed a facile synthetic method for preparing N-heterocycles that involves the in situ generation of an N-X bond using tert-butyl hypochlorite or tert-butyl hypoiodite (tert-BuOI). Treatment of alkenylamides containing an active hydrogen on the nitrogen with tert-BuOI led to the production of various N-heterocycles via intramolecular cyclization. Iodination of readily available sulfonamides or carboxamides with tert-BuOI generated reactive N-iodinated amides, which smoothly reacted with olefins to give aziridines or oxazolines. The reaction of fullerene, C(60), with CT also led to aziridination: the resulting aziridinofullerene underwent a unique rearrangement to an azafulleroid. Chlorination of readily available amide derivatives with tert-BuOCl, followed by a reaction with C(60) in the presence of an organic base, afforded aziridinofullerenes with various substituents on the nitrogen. The results in this Account contribute to the development of convenient methods for constructing simple and useful heterocycles. PMID:19480410

  10. Rwanda.

    Science.gov (United States)

    1985-09-01

    Rwanda's population characteristics, history, government, political situation, economy, and foreign relations were briefly discribed. Rwanda, a small African country, covers an area of 10,160 square miles and is situated between Zaire, Uganda, Burundi, and Tanzania. During the 1400s, Tutsi cattle breeders moved into the region and turned the Hutu farmers, the original occupants of the region, into serfs. The Tutsi maintained their dominant position until 1959. Rwanda was a German protectorate between 1899-1916 and a territory under the administration of Belgium following World War I. During the 1950s, the Tutsi resisted efforts by the Belgians to democratize the country, and in 1959, the Party of the Hutu Emancipation Movement (PARMEHUTU) overthrew the Tutsi monarchy. The PARMEHUTU leader, Gregoire Kayibanda was selected by the elected unicameral National Assembly to head the government following the granting of independence to Rwanda in 1962. In 1973 growing government inefficiency and corruption led to the takeover of the country by the military leader, Major General Juvenal Habyarimana, who in 1975 formed the National Revolutionary Movement for Development. Although civilian rule is being gradually restored, Habyarimana, who is now the elected president of the country, retains considerable power. In addition to the president, the country is run by a 17-member cabinet and a 70-member elected legislative body, the National Development Council. The current goverment is strongly committed to the developing the country's economy. Rwanda is a poor and overpopulated country, and its economy is based mainly on subsistence level farming. 93% of the work force is engaged in agriculture. 35% of the gross national product (GNP) is derived from agriculture, and the main agricultural products are tea, pyrethrum, and cinchona. Small-scale industries account for another 21.6% of the GNP. The government is working to increase the country's energy sources and to attract foreign

  11. [Prescription of medicines by two medical officers in Jutland in 1797. An analysis of the prescription practice of C.D. Hahn, Physicus of Aarhus Diocese, and K.N. Carstensen, Physicus of Aalborg Diocese].

    Science.gov (United States)

    Kruse, Poul R; Kruse, Edith; Wulff, Henrik R; Jungersen, Kirsten

    2008-01-01

    , electuaries, powders, teas and other herbs. Medicines for external use were usually ointments. In a number of cases Hahn prescribed pills, whereas Carstensen did not do so, although the production of pills at that time was common practice. Carstensen paid greater attention to the durability of the prescribed medicines than Hahn, probably because Carstensen's patients came from all of Northern Jutland. Therefore, it was important in his case that the keeping quality of the medicines permitted a time-consuming transport from pharmacy to patient and storage by the patient during the whole course of treatment. In contrast, most of Hahn's patients lived in Aarhus and surroundings. We compared the 22 substances used most frequently by Hahn and the 22 used most frequently by Carstensen. In both cases these included (in alphabetical order): bitter orange peel, camphor, cinchona, ether, peppermint, potassium carbonate, potassium tartrate and rhubarb roots. 60% of the substances in the preparations by either doctor were herbal drugs and 40% mineral or other chemical substances. Both Hahn and Carstensen favoured "evacuative" treatment, according to the theory of humoral pathology, using laxatives, diuretics and sudorifics. However, their choice of medicines differed, and, in contrast to Carstensen, Hahn also frequently prescribed emetics. The two doctors rarely prescribed the chemical substances recommended by the iatrochemists. PMID:18548942

  12. Vladimir Prelog i Zavod za organsku kemiju

    Directory of Open Access Journals (Sweden)

    Jakopčić, K.

    2007-03-01

    -operation from the small but prosperous pharmaceutical company "Kaštel" in Zagreb. On behalf of the agreement, Prelog and his department obtained funds to fit up the laboratory and to start very prosperous research in the synthesis and studies of pharmaceutically interesting compounds. With his assistants, students and other collaborators, Prelog started research of cinchona bark alkaloids, preferentially oriented to the synthesis of quinine. For example, Prelog's method of double intramolecular alkylation to synthetize the quinuclidine moiety of quinine was patented by "Kaštel". With R. Seiwerth he developed the first useful synthesis of adamantane. Prelog's group started research in the field of sulphonamides and commercial success of "Streptazole" stimulated the development of the research laboratories within "Kaštel". The collaboration in the research continued in fields of other chemotherapeutics, analeptics, spasmolitics, barbiturates etc. Within the period 1935-1941, Prelog published 48 scientific papers and 8 patents. In less than seven years, his results enormously influenced the entire organic chemistry in Zagreb till nowadays. Under the confused and uncertain circumstances caused by the beginning of World War II, Prelog left Zagreb in 1941 and continued his extraordinary scientific career at the ETH in Zürich.During the war (1942-1945 the tuition and the Department were run by Dr. Rativoj Seiwerth, former collaborator and first assistant to V. Prelog. In almost unbelievable conditions, the young assistant, then assistant professor (since January 1943, R. Seiwerth fully succeeded in continuing most activities founded by Professor Prelog. After the war (1945, R. Seiwerth was forced to resign. Nevertheless, soon after R. Seiwerth continued his research work, firstly in the Institute for Industrial Research in Zagreb (1946-1952, and later in the Research Institute of "Pliva" in Zagreb. He retired in 1980.In post-war conditions (1945/46, the activity of the Technical