Base de dados : MEDLINE
Pesquisa : B01.650.940.800.575.912.250.198.500.300 [Categoria DeCS]
Referências encontradas : 7 [refinar]
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  1 / 7 MEDLINE  
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[PMID]:27420351
[Au] Autor:Lieberherr C; Zhang G; Grafen A; Singethan K; Kendl S; Vogt V; Maier J; Bringmann G; Schneider-Schaulies J
[Ad] Endereço:Institute for Virology and Immunobiology, University of Würzburg, Würzburg, Germany.
[Ti] Título:The Plant-Derived Naphthoquinone Droserone Inhibits In Vitro Measles Virus Infection.
[So] Source:Planta Med;83(3-04):232-238, 2017 Feb.
[Is] ISSN:1439-0221
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:The naphthoquinone droserone ( ) is a natural product occurring in dicotyledonous plants. We have now observed that the addition of during infection of tissue culture cells with measles virus considerably reduced the infection. Interestingly, the infection was inhibited only when droserone ( ) was added during virus entry, but not when added to the cells prior to virus uptake or after virus uptake. These findings suggest that interacts with viral particles to reduce infectivity. The formation of progeny measles virus particles was inhibited to 50 % by droserone ( ) at a concentration (IC ) of approximately 2 µM with a half-maximal cytotoxicity (CC ) of about 60 µM for Vero cells. Other tested naphthoquinone derivatives, among them the likewise natural plumbagin ( ), but also synthetic analogs, were either more cytotoxic or not as effective as . Thus, our data do not support the development of naphthoquinone derivatives into antiviral compounds, but suggest that they may be interesting research tools to study measles virus entry into cells.
[Mh] Termos MeSH primário: Vírus do Sarampo/isolamento & purificação
Sarampo/tratamento farmacológico
Naftoquinonas/farmacologia
[Mh] Termos MeSH secundário: Animais
Antivirais/farmacologia
Sobrevivência Celular/efeitos dos fármacos
Células Cultivadas
Cercopithecus aethiops
Dioncophyllaceae/química
Técnicas In Vitro
Concentração Inibidora 50
Magnoliopsida/química
Naftoquinonas/química
Células Vero
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antiviral Agents); 0 (Naphthoquinones); YAS4TBQ4OQ (plumbagin)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160716
[St] Status:MEDLINE
[do] DOI:10.1055/s-0042-111825


  2 / 7 MEDLINE  
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[PMID]:27438403
[Au] Autor:Bringmann G; Irmer A; Büttner T; Schaumlöffel A; Zhang G; Seupel R; Feineis D; Fester K
[Ad] Endereço:Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
[Ti] Título:Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African Liana Triphyophyllum peltatum.
[So] Source:J Nat Prod;79(8):2094-103, 2016 Aug 26.
[Is] ISSN:1520-6025
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Root cultures of the West African liana Triphyophyllum peltatum were initiated from stem explants of in vitro cultivated shoots. From these organ cultures, three new binaphthalenes, one binaphthoquinone, and two (bi)naphthalene glucosides were isolated, with substitution patterns related to those of the naphthylisoquinoline alkaloids, which are the "normal" main metabolites of T. peltatum. The structures of the diglucoside dioncoquinoside A (1) and of the axially chiral biaryls triphyoquinols A1 (3), A2 (4), and B (5), triphyoquinoside A (6), and triphyoquinone A (7) were elucidated by spectroscopic analysis (HRESIMS, 1D and 2D NMR) and by application of electronic circular dichroism (ECD) spectroscopy in combination with the exciton chirality method and quantum-chemical ECD calculations. The root cultures likewise produced the known alkaloids dioncophylline A (8), 5'-O-demethyldioncophylline A (9), dioncopeltine A (10), habropetaline A (11), and 5'-O-methyldioncophylline D (12a/b), the naphthalene glucoside plumbaside A (2), and the naphthoquinones plumbagin (13), droserone (14), and 8-hydroxydroserone (15).
[Mh] Termos MeSH primário: Alcaloides/isolamento & purificação
Dioncophyllaceae/química
Naftalenos/isolamento & purificação
Naftoquinonas/isolamento & purificação
[Mh] Termos MeSH secundário: África Ocidental
Alcaloides/química
Isoquinolinas/química
Estrutura Molecular
Naftalenos/química
Naftoquinonas/química
Extratos Vegetais
Raízes de Plantas/química
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkaloids); 0 (Isoquinolines); 0 (Naphthalenes); 0 (Naphthoquinones); 0 (Plant Extracts); 0 (hydroxydroserone); 60142-17-8 (dioncophylline A); YAS4TBQ4OQ (plumbagin)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170502
[Lr] Data última revisão:
170502
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160721
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jnatprod.6b00439


  3 / 7 MEDLINE  
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[PMID]:26388556
[Au] Autor:Ibrahim SR; Mohamed GA
[Ad] Endereço:Department of Pharmacognosy and Pharmaceutical Chemistry, College of Pharmacy, Taibah University, Al Madinah Al Munawwarah 30078, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt. Electronic address: sabrinshaur@gmail.com.
[Ti] Título:Naphthylisoquinoline alkaloids potential drug leads.
[So] Source:Fitoterapia;106:194-225, 2015 Oct.
[Is] ISSN:1873-6971
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Naphthylisoquinolines are a group of structurally diverse secondary metabolites, consisting of naphthalene and isoquinoline moieties. Naturally occurring naphthylisoquinolines have so far been found only in the small palaeotropic families Dioncophyllaceae and Ancistrocladaceae. They have been shown to exhibit a diverse array of biological activities. Herein, we review the research on the occurrence, isolation, identification, biological activities, and biosynthesis of this class of compounds published from 1995 till now. Moreover, their chemotaxonomic relevance and molecular targets of action have been discussed. More than 125 metabolites are described and 99 references are cited.
[Mh] Termos MeSH primário: Alcaloides/farmacologia
Isoquinolinas/farmacologia
Compostos Fitoquímicos/farmacologia
[Mh] Termos MeSH secundário: Alcaloides/isolamento & purificação
Antiprotozoários/isolamento & purificação
Antiprotozoários/farmacologia
Dioncophyllaceae/química
Isoquinolinas/isolamento & purificação
Magnoliopsida/química
Estrutura Molecular
Compostos Fitoquímicos/isolamento & purificação
Metabolismo Secundário
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Alkaloids); 0 (Antiprotozoal Agents); 0 (Isoquinolines); 0 (Phytochemicals); JGX76Y85M6 (isoquinoline)
[Em] Mês de entrada:1602
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150922
[St] Status:MEDLINE


  4 / 7 MEDLINE  
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[PMID]:22019229
[Au] Autor:Bringmann G; Zhang G; Hager A; Moos M; Irmer A; Bargou R; Chatterjee M
[Ad] Endereço:Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
[Ti] Título:Anti-tumoral activities of dioncoquinones B and C and related naphthoquinones gained from total synthesis or isolation from plants.
[So] Source:Eur J Med Chem;46(12):5778-89, 2011 Dec.
[Is] ISSN:1768-3254
[Cp] País de publicação:France
[La] Idioma:eng
[Ab] Resumo:Dioncoquinones belong to a family of natural naphthoquinone products of interest due to their promising anti-tumoral and anti-infective activities. In particular, dioncoquinones A (5) and B (6) have been shown to be highly active against Leishmania major and multiple myeloma cells without any significant toxicity toward normal blood cells. Their effective concentrations against multiple myeloma cell lines were similar to those of melphalan, a well known DNA-alkylating agent used in a standard therapy against B cell lymphoma and multiple myeloma. We report on the first total synthesis of the highly oxygenated anti-tumoral agent dioncoquinone B (6) and the isolation of its new, even higher-oxygenated analogs, dioncoquinones C (7), D (8), and E (9), from cell cultures of Triphyophyllum peltatum. In addition, several derivatives of these compounds were synthesized, including dioncoquinone C (7), and a small library of naphthoquinones was created. Furthermore, the first structure-activity relationship (SAR) study on this class of compounds was conducted, showing that each of the three hydroxy groups, at C-3, C-5, and C-6, is required for improved anti-tumoral activities and decreased cytotoxicities.
[Mh] Termos MeSH primário: Antineoplásicos/química
Antineoplásicos/farmacologia
Dioncophyllaceae/química
Mieloma Múltiplo/tratamento farmacológico
Naftoquinonas/química
Naftoquinonas/farmacocinética
[Mh] Termos MeSH secundário: Antineoplásicos/síntese química
Antineoplásicos/isolamento & purificação
Apoptose/efeitos dos fármacos
Linhagem Celular Tumoral
Seres Humanos
Naftoquinonas/síntese química
Naftoquinonas/isolamento & purificação
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Naphthoquinones)
[Em] Mês de entrada:1202
[Cu] Atualização por classe:111114
[Lr] Data última revisão:
111114
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:111025
[St] Status:MEDLINE
[do] DOI:10.1016/j.ejmech.2011.09.012


  5 / 7 MEDLINE  
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[PMID]:18723197
[Au] Autor:Bringmann G; Rüdenauer S; Irmer A; Bruhn T; Brun R; Heimberger T; Stühmer T; Bargou R; Chatterjee M
[Ad] Endereço:Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
[Ti] Título:Antitumoral and antileishmanial dioncoquinones and ancistroquinones from cell cultures of Triphyophyllum peltatum (Dioncophyllaceae) and Ancistrocladus abbreviatus (Ancistrocladaceae).
[So] Source:Phytochemistry;69(13):2501-9, 2008 Oct.
[Is] ISSN:0031-9422
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:From the methanolic extracts of solid callus cultures from two species of the closely related palaeotropical plant families Dioncophyllaceae and Ancistrocladaceae seven new natural naphthoquinones were isolated, dioncoquinones A (4) and B (5) from Triphyophyllum peltatum, and ancistroquinones B (6), C (7), D (9), E (10), and F (12) from Ancistrocladus abbreviatus. Their structures were elucidated by spectroscopic, chemical, and computational methods. Furthermore, the already known naphthoquinones plumbagin (2), droserone (3), malvone A (8), and nepenthone A (11) were found in the extract of A. abbreviatus. Dioncoquinones A (4) and B (5) showed good - and specific - activity against Leishmania major, while they were not active against other protozoic parasites. Moreover, treatment with 4 and 5 strongly induced apoptosis in human tumor cells derived from two different B cell malignancies, B cell lymphoma and multiple myeloma, without any significant toxicity towards normal peripheral mononuclear blood cells.
[Mh] Termos MeSH primário: Antimaláricos/farmacologia
Antineoplásicos/farmacologia
Dioncophyllaceae/química
Magnoliopsida/química
[Mh] Termos MeSH secundário: Animais
Antimaláricos/química
Antineoplásicos/química
Apoptose/efeitos dos fármacos
Linhagem Celular Tumoral
Sobrevivência Celular/efeitos dos fármacos
Células Cultivadas
Dioncophyllaceae/citologia
Seres Humanos
Espectroscopia de Ressonância Magnética
Estrutura Molecular
Naftoquinonas/química
Naftoquinonas/farmacologia
Extratos Vegetais/química
Extratos Vegetais/farmacologia
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antimalarials); 0 (Antineoplastic Agents); 0 (Naphthoquinones); 0 (Plant Extracts)
[Em] Mês de entrada:0902
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:080830
[St] Status:MEDLINE
[do] DOI:10.1016/j.phytochem.2008.06.019


  6 / 7 MEDLINE  
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[PMID]:17263326
[Au] Autor:Frosch T; Schmitt M; Noll T; Bringmann G; Schenzel K; Popp J
[Ad] Endereço:Institut für Physikalische Chemie, Friedrich-Schiller-Universität Jena, Helmholtzweg 4, D-07743 Jena, Germany.
[Ti] Título:Ultrasensitive in situ tracing of the alkaloid dioncophylline A in the tropical liana Triphyophyllum peltatum by applying deep-UV resonance Raman microscopy.
[So] Source:Anal Chem;79(3):986-93, 2007 Feb 01.
[Is] ISSN:0003-2700
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:UV resonance Raman microspectroscopy was applied for a localization of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A in very low concentrations in different parts of the samples (e.g., in the roots) of the tropical liana Triphyophyllum peltatum. The application of resonance Raman microspectroscopy was characterized by a very high sensitivity and selectivity. It was possible to assign the resonance Raman spectra of dioncophylline A, dioncophylline C, and dioncopeltine A by means of a combination of NIR Raman spectroscopy and DFT calculations. The UV resonance Raman spectra of T. peltatum are very well resembled by the spectra of dioncophylline A, while they can be clearly distinguished from the spectra of dioncophylline C and dioncopeltine A. This distinction between the various naphthylisoquinolines was possible by the two modes at 1356 and 1613 cm-1. These two modes were assigned to C=C stretching and CH bending vibrations. The presented results of a highly sensitive and selective in situ localization of the active agent dioncophylline A in different parts of the plant material of T. peltatum are of high importance for the acquisition of new antimalarials and for plant science in general.
[Mh] Termos MeSH primário: Alcaloides/análise
Dioncophyllaceae/química
Isoquinolinas/análise
Análise Espectral Raman/métodos
[Mh] Termos MeSH secundário: Antimaláricos/análise
Naftóis/análise
Plantas/química
Sensibilidade e Especificidade
Raios Ultravioleta
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkaloids); 0 (Antimalarials); 0 (Isoquinolines); 0 (Naphthols); 0 (dioncophylline C); 60142-17-8 (dioncophylline A)
[Em] Mês de entrada:0703
[Cu] Atualização por classe:070131
[Lr] Data última revisão:
070131
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:070201
[St] Status:MEDLINE


  7 / 7 MEDLINE  
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[PMID]:16453274
[Au] Autor:Frosch T; Schmitt M; Schenzel K; Faber JH; Bringmann G; Kiefer W; Popp J
[Ad] Endereço:Institut für Physikalische Chemie, Friedrich-Schiller-Universität Jena, Helmholtzweg 4, D-07743 Jena, Germany.
[Ti] Título:In vivo localization and identification of the antiplasmodial alkaloid dioncophylline A in the tropical liana Triphyophyllum peltatum by a combination of fluorescence, near infrared Fourier transform Raman microscopy, and density functional theory calculations.
[So] Source:Biopolymers;82(4):295-300, 2006 Jul.
[Is] ISSN:0006-3525
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Near infrared Fourier transform (NIR FT) micro Raman spectroscopy in combination with density functional theory (DFT) calculations has been applied for an in vivo localization of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A (1) in the tropical liana Triphyophyllum peltatum. Fluorescence microscopy images suggest finding this active agent in 10 mum big inclusions located in the cortex of the stem or the beginning of the leaves. By means of spatially resolved FT Raman micro spectroscopy, we could detect dioncophylline A (1) in these inclusions. FT Raman spectroscopy is an extremely selective tool capable of differentiating between various structurally similar naphthylisoquinoline alkaloids. With the help of DFT calculations, we succeeded in assigning the differences found in the FT Raman spectra of the various naphthylisoquinolines to nuC=C vibrations of the naphthyl ring. The presented results are of relevance for the investigation and extraction of new antimalarial active agents.
[Mh] Termos MeSH primário: Dioncophyllaceae/química
Isoquinolinas/análise
Microscopia de Fluorescência/métodos
Plantas Medicinais/química
Espectroscopia de Infravermelho com Transformada de Fourier/métodos
[Mh] Termos MeSH secundário: Algoritmos
Alcaloides/análise
Alcaloides/química
Antimaláricos/análise
Antimaláricos/química
Isoquinolinas/química
Estrutura Molecular
Naftalenos/química
Espectroscopia de Luz Próxima ao Infravermelho/métodos
Análise Espectral Raman/métodos
Vibração
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Alkaloids); 0 (Antimalarials); 0 (Isoquinolines); 0 (Naphthalenes); 2166IN72UN (naphthalene); 60142-17-8 (dioncophylline A)
[Em] Mês de entrada:0607
[Cu] Atualização por classe:121115
[Lr] Data última revisão:
121115
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:060203
[St] Status:MEDLINE



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