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Steven M Weinreb - One of the best experts on this subject based on the ideXlab platform.

Arildo Jose Braz De Oliveira - One of the best experts on this subject based on the ideXlab platform.

  • Estudo de seis especies do genero aspidosperma utilizando GC, GC/MS e HPLC : analise qualitativa e quantitativa. Teste bioautografico; cultura de tecidos e celulas vegetais e rota de preparação dos compostos dimericos ramiflorina A e ramiflorina B
    2017
    Co-Authors: Arildo Jose Braz De Oliveira
    Abstract:

    Resumo: O desenvolvimento de um método de análise rápido e econômico de plantas contendo alcalóides indólicos utilizando CG, CG/EM e CLAE foi a principal proposição desta tese. Nosso grupo de pesquisa tem estudado espécies do gênero Aspidosperma e nesta tese o objetivo foi estudar seis espécies e realizar a análise qualitativa e quantitativa dos alcalóides por CG, CG/EM e CLAE. O estudo fitoquímico de cinco espécies permitiu o isolamento de vinte e duas substâncias puras, entre elas quatorze que não haviam sido isoladas anteriormente destas espécies. A (+)-aspidospermina, (+)-pirifolidina, (-)- aspidofractinina, (-)-aspidofilina, (+)-15-desmetóxi-pirifolina e (+)-pirifolina (Aspidosperma olivaceum); N-acetil-cilindrocarina e 12-O-metil-21-oxo-aspidoalbina (A. polyneuron); (-)- aspidospermina, (+)-1,2-desidro-aspidospermidina e geissosvellina (A. dispermum ); 19-E-isositsiriquina (A. ramiflorum); 15-metóxi-aspidospermina e 15 metóxi-pirifolidina (A. pyrifolium), estas duas ultimas são substâncias novas. As substâncias isoladas foram utilizadas como padrões nos estudos cromatográficos e o método de análise exigiu pequena quantidade do extrato da planta, utilizando o método do padrão interno para quantificação. Testes autobiograficos, antibacterianos e antifungicos nos extratos e padrões isolados mostraram uma potente ação antibacteriana. Os melhores resultado ocorreram nas substâncias (+)-ramiflorina A e (+)-ramiflorina B, (+)-aparicina, (-)-aspidospermina, (-)-N- acetil-cilindrocarina e normacusina B. Os resultados obtidos nas espécies A. ramiflorum e A. polyneuron incentivou-nos a desenvolver experimentos de cultura in vitro de tecidos e células vegetais, visando produzir os alcalóides ativos. A. ramiflorum foi a espécie que apresentou os melhores resultados, levando a produção dos alcalóides ramiflorina A e ramiflorina B. A análise utilizando CG, CG/EM e CLAE do extratos A. ramiflorum revelou que o (+)-10-metóxi-geissoschizol (10MG) estava presente em quantidades consideráveis, o que sugeriu-nos realizar a semi-síntese dos alcalóides ramiflorina A e B, utilizando esta substância como substrato. Portanto testamos a reação em um modelo o triptofol, cuja estrutura é similar ao 10MG. O triptofol foi condensado com a triptamina para dar uma substância dimérica que foi identificada por métodos fisicos. Estes resultados mostram a viabilidade de se preparar as ramiflorinas A e B por esta semi-síntese proposta.Abstract: The development of a fast and economical method of analysis in plant that contain indolic alkaloid using GC and GC/MS techniques was the principal aim of this thesis. Our research group have been studying species from Aspidosperma genera and the subject of this thesis, was to study steam bark extracts of six species as will to perform qualitative and quantitative analysis by GC, GC/MS and HPLC. The phytochemical study of the plants resulted in the isolation of twenty-two pure compounds, among which, fourteen have not been previously, described these species. The (+)-aspidospermine, (+)-pyrifolidine, (-)-aspidofractinine, (-)-aspidofiline, (+)-15-demethoxypyrifoline and (+)-pyrifoline (Aspidosperma olivaceum); N-acetyl-cylindrocarine and 12-O-methyl-21-oxo-aspidoalbine (A. polyneuron); (-)-aspidospermine, (+)-1 ,2-dehidroaspidospermidine and geissosvelline (A. dispermum); 19-E-isositsirikine (A. ramiflorum); 15-methoxyaspidospermine and 15 methoxypyrifolidine (A. pyrifolium), and the latter two are novel compounds. These compounds isolated were used as standards in the chromatographic studies and the analytical method required small quantities of the plant extracts, using internal standard method for quantification. Bioautographic test, antibacterial and antifungi, using extracts and pure substances showed strong antibacterial action. The best results were obtained with the substances (+)-ramiflorine A e (+)-ramiflorine B, (+)-apparicine, (-)-aspidospermine, (-)-N-acetyl-cylindrocarine and normacusine B. The results obtained with A. ramiflorum and A. polyneuron encouraged us to develop assays with tissue and plant cell culture to produce the active alkaloids. A. ramiflorum showed the first good results with production of (+)- ramiflorine A and (+)-ramiflorine B. In the GC, GC/MS and HPLC analysis of extract the A. ramiflorum reveled that one component, 10-methoxygeissochizol (10MG), in considerable concentration, this suggested to us the possibility of semi-synthesis of alkaloids (+) -ramiflorine A and B, using 10MG as a substrate. Therefore, we tested in reaction using a tryptophol model with has a similar structure to the 10MG. The condensation of tryptophol with tryptamine gave the dimmeric compound which was identified by spectroscopy data. These results show that the semi-synthesis of (+)-ramiflorine A e (+)-ramiflorine B is possible

  • anti malarial activity of indole alkaloids isolated from aspidosperma olivaceum
    Malaria Journal, 2014
    Co-Authors: Talita Pc Chierrito, Arildo Jose Braz De Oliveira, Isabel M De Andrade, Isabela P Ceravolo, Antoniana U Krettli, Anna Caroline Campos Aguiar, Regina Aparecida Correia Goncalves
    Abstract:

    Several species of Aspidosperma (Apocynaceae) are used as treatments for human diseases in the tropics. Aspidosperma olivaceum, which is used to treat fevers in some regions of Brazil, contains the monoterpenoid indole alkaloids (MIAs) aspidoscarpine, uleine, apparicine, and N-methyl-tetrahydrolivacine. Using bio-guided fractionation and cytotoxicity testing in a human hepatoma cell line, several plant fractions and compounds purified from the bark and leaves of the plant were characterized for specific therapeutic activity (and selectivity index, SI) in vitro against the blood forms of Plasmodium falciparum. The activity of A. olivaceum extracts, fractions, and isolated compounds was evaluated against chloroquine (CQ)-resistant P. falciparum blood parasites by in vitro testing with radiolabelled [3H]-hypoxanthine and a monoclonal anti-histidine-rich protein (HRPII) antibody. The cytotoxicity of these fractions and compounds was evaluated in a human hepatoma cell line using a 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) assay, and the SI was calculated as the ratio between the toxicity and activity. Two leaf fractions were tested in mice with Plasmodium berghei. All six fractions from the bark and leaf extracts were active in vitro at low doses (IC50 < 5.0 μg/mL) using the anti-HRPII test, and only two (the neutral and basic bark fractions) were toxic to a human cell line (HepG2). The most promising fractions were the crude leaf extract and its basic residue, which had SIs above 50. Among the four pure compounds evaluated, aspidoscarpine in the bark and leaf extracts showed the highest SI at 56; this compound, therefore, represents a possible anti-malarial drug that requires further study. The acidic leaf fraction administered by gavage to mice with blood-induced malaria was also active. Using a bio-monitoring approach, it was possible to attribute the anti-P. falciparum activity of A. olivaceum to aspidoscarpine and, to a lesser extent, N-methyl-tetrahydrolivacine; other isolated MIA molecules were active but had lower SIs due to their higher toxicities. These results stood in contrast to previous work in which the anti-malarial activity of other Aspidosperma species was attributed to uleine.

  • Estudo de seis especies do genero aspidosperma utilizando GC, GC/MS e HPLC : analise qualitativa e quantitativa. Teste bioautografico; cultura de tecidos e celulas vegetais e rota de preparação dos compostos dimericos ramiflorina A e ramiflorina B
    Universidade Estadual de Campinas . Instituto de Quimica, 1999
    Co-Authors: Arildo Jose Braz De Oliveira
    Abstract:

    O desenvolvimento de um método de análise rápido e econômico de plantas contendo alcalóides indólicos utilizando CG, CG/EM e CLAE foi a principal proposição desta tese. Nosso grupo de pesquisa tem estudado espécies do gênero Aspidosperma e nesta tese o objetivo foi estudar seis espécies e realizar a análise qualitativa e quantitativa dos alcalóides por CG, CG/EM e CLAE. O estudo fitoquímico de cinco espécies permitiu o isolamento de vinte e duas substâncias puras, entre elas quatorze que não haviam sido isoladas anteriormente destas espécies. A (+)-aspidospermina, (+)-pirifolidina, (-)- aspidofractinina, (-)-aspidofilina, (+)-15-desmetóxi-pirifolina e (+)-pirifolina (Aspidosperma olivaceum); N-acetil-cilindrocarina e 12-O-metil-21-oxo-aspidoalbina (A. polyneuron); (-)- aspidospermina, (+)-1,2-desidro-aspidospermidina e geissosvellina (A. dispermum ); 19-E-isositsiriquina (A. ramiflorum); 15-metóxi-aspidospermina e 15 metóxi-pirifolidina (A. pyrifolium), estas duas ultimas são substâncias novas. As substâncias isoladas foram utilizadas como padrões nos estudos cromatográficos e o método de análise exigiu pequena quantidade do extrato da planta, utilizando o método do padrão interno para quantificação. Testes autobiograficos, antibacterianos e antifungicos nos extratos e padrões isolados mostraram uma potente ação antibacteriana. Os melhores resultado ocorreram nas substâncias (+)-ramiflorina A e (+)-ramiflorina B, (+)-aparicina, (-)-aspidospermina, (-)-N- acetil-cilindrocarina e normacusina B. Os resultados obtidos nas espécies A. ramiflorum e A. polyneuron incentivou-nos a desenvolver experimentos de cultura in vitro de tecidos e células vegetais, visando produzir os alcalóides ativos. A. ramiflorum foi a espécie que apresentou os melhores resultados, levando a produção dos alcalóides ramiflorina A e ramiflorina B. A análise utilizando CG, CG/EM e CLAE do extratos A. ramiflorum revelou que o (+)-10-metóxi-geissoschizol (10MG) estava presente em quantidades consideráveis, o que sugeriu-nos realizar a semi-síntese dos alcalóides ramiflorina A e B, utilizando esta substância como substrato. Portanto testamos a reação em um modelo o triptofol, cuja estrutura é similar ao 10MG. O triptofol foi condensado com a triptamina para dar uma substância dimérica que foi identificada por métodos fisicos. Estes resultados mostram a viabilidade de se preparar as ramiflorinas A e B por esta semi-síntese proposta.The development of a fast and economical method of analysis in plant that contain indolic alkaloid using GC and GC/MS techniques was the principal aim of this thesis. Our research group have been studying species from Aspidosperma genera and the subject of this thesis, was to study steam bark extracts of six species as will to perform qualitative and quantitative analysis by GC, GC/MS and HPLC. The phytochemical study of the plants resulted in the isolation of twenty-two pure compounds, among which, fourteen have not been previously, described these species. The (+)-aspidospermine, (+)-pyrifolidine, (-)-aspidofractinine, (-)-aspidofiline, (+)-15-demethoxypyrifoline and (+)-pyrifoline (Aspidosperma olivaceum); N-acetyl-cylindrocarine and 12-O-methyl-21-oxo-aspidoalbine (A. polyneuron); (-)-aspidospermine, (+)-1 ,2-dehidroaspidospermidine and geissosvelline (A. dispermum); 19-E-isositsirikine (A. ramiflorum); 15-methoxyaspidospermine and 15 methoxypyrifolidine (A. pyrifolium), and the latter two are novel compounds. These compounds isolated were used as standards in the chromatographic studies and the analytical method required small quantities of the plant extracts, using internal standard method for quantification. Bioautographic test, antibacterial and antifungi, using extracts and pure substances showed strong antibacterial action. The best results were obtained with the substances (+)-ramiflorine A e (+)-ramiflorine B, (+)-apparicine, (-)-aspidospermine, (-)-N-acetyl-cylindrocarine and normacusine B. The results obtained with A. ramiflorum and A. polyneuron encouraged us to develop assays with tissue and plant cell culture to produce the active alkaloids. A. ramiflorum showed the first good results with production of (+)- ramiflorine A and (+)-ramiflorine B. In the GC, GC/MS and HPLC analysis of extract the A. ramiflorum reveled that one component, 10-methoxygeissochizol (10MG), in considerable concentration, this suggested to us the possibility of semi-synthesis of alkaloids (+) -ramiflorine A and B, using 10MG as a substrate. Therefore, we tested in reaction using a tryptophol model with has a similar structure to the 10MG. The condensation of tryptophol with tryptamine gave the dimmeric compound which was identified by spectroscopy data. These results show that the semi-synthesis of (+)-ramiflorine A e (+)-ramiflorine B is possible

Pradeep S Chauhan - One of the best experts on this subject based on the ideXlab platform.

S Anuradha - One of the best experts on this subject based on the ideXlab platform.

  • alkaloids from tabernaemontana divaricata
    Phytochemistry, 1995
    Co-Authors: S Anuradha
    Abstract:

    Abstract An ethanolic extract of the leaves of Tabernaemontana divaricata (double flower variety) furnished, in addition to voaphylline, N 1 -methylvoaphylline, voaharine, pachysiphine, apparicine and conophylline, two new alkaloids, ( − )-mehranine and the dimeric indole conofoline. The structures of the new alkaloids were elucidated by spectral methods.

Antoniana U Krettli - One of the best experts on this subject based on the ideXlab platform.

  • Anti-malarial activity of indole alkaloids isolated from Aspidosperma olivaceum
    Malaria Journal, 2014
    Co-Authors: Talita Pc Chierrito, Anna Cc Aguiar, Isabel M De Andrade, Isabela P Ceravolo, Regina Ac Gonçalves, Arildo Jb De Oliveira, Antoniana U Krettli
    Abstract:

    Background Several species of Aspidosperma (Apocynaceae) are used as treatments for human diseases in the tropics. Aspidosperma olivaceum , which is used to treat fevers in some regions of Brazil, contains the monoterpenoid indole alkaloids (MIAs) aspidoscarpine, uleine, apparicine, and N-methyl-tetrahydrolivacine. Using bio-guided fractionation and cytotoxicity testing in a human hepatoma cell line, several plant fractions and compounds purified from the bark and leaves of the plant were characterized for specific therapeutic activity (and selectivity index, SI) in vitro against the blood forms of Plasmodium falciparum . Methods The activity of A. olivaceum extracts, fractions, and isolated compounds was evaluated against chloroquine (CQ)-resistant P. falciparum blood parasites by in vitro testing with radiolabelled [^3H]-hypoxanthine and a monoclonal anti-histidine-rich protein (HRPII) antibody. The cytotoxicity of these fractions and compounds was evaluated in a human hepatoma cell line using a 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) assay, and the SI was calculated as the ratio between the toxicity and activity. Two leaf fractions were tested in mice with Plasmodium berghei . Results All six fractions from the bark and leaf extracts were active in vitro at low doses (IC_50 

  • anti malarial activity of indole alkaloids isolated from aspidosperma olivaceum
    Malaria Journal, 2014
    Co-Authors: Talita Pc Chierrito, Arildo Jose Braz De Oliveira, Isabel M De Andrade, Isabela P Ceravolo, Antoniana U Krettli, Anna Caroline Campos Aguiar, Regina Aparecida Correia Goncalves
    Abstract:

    Several species of Aspidosperma (Apocynaceae) are used as treatments for human diseases in the tropics. Aspidosperma olivaceum, which is used to treat fevers in some regions of Brazil, contains the monoterpenoid indole alkaloids (MIAs) aspidoscarpine, uleine, apparicine, and N-methyl-tetrahydrolivacine. Using bio-guided fractionation and cytotoxicity testing in a human hepatoma cell line, several plant fractions and compounds purified from the bark and leaves of the plant were characterized for specific therapeutic activity (and selectivity index, SI) in vitro against the blood forms of Plasmodium falciparum. The activity of A. olivaceum extracts, fractions, and isolated compounds was evaluated against chloroquine (CQ)-resistant P. falciparum blood parasites by in vitro testing with radiolabelled [3H]-hypoxanthine and a monoclonal anti-histidine-rich protein (HRPII) antibody. The cytotoxicity of these fractions and compounds was evaluated in a human hepatoma cell line using a 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) assay, and the SI was calculated as the ratio between the toxicity and activity. Two leaf fractions were tested in mice with Plasmodium berghei. All six fractions from the bark and leaf extracts were active in vitro at low doses (IC50 < 5.0 μg/mL) using the anti-HRPII test, and only two (the neutral and basic bark fractions) were toxic to a human cell line (HepG2). The most promising fractions were the crude leaf extract and its basic residue, which had SIs above 50. Among the four pure compounds evaluated, aspidoscarpine in the bark and leaf extracts showed the highest SI at 56; this compound, therefore, represents a possible anti-malarial drug that requires further study. The acidic leaf fraction administered by gavage to mice with blood-induced malaria was also active. Using a bio-monitoring approach, it was possible to attribute the anti-P. falciparum activity of A. olivaceum to aspidoscarpine and, to a lesser extent, N-methyl-tetrahydrolivacine; other isolated MIA molecules were active but had lower SIs due to their higher toxicities. These results stood in contrast to previous work in which the anti-malarial activity of other Aspidosperma species was attributed to uleine.

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