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[PMID]:28641463
[Au] Autor:Du SZ; Kuang F; Liu Y; Chen YG; Zhan R
[Ad] Endereço:a School of Chemistry and Chemical Engineering , Yunnan Normal University , Kunming , China.
[Ti] Título:A new dimeric diarylpropane from Horsfieldia tetratepala.
[So] Source:Nat Prod Res;32(2):162-166, 2018 Jan.
[Is] ISSN:1478-6427
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Five compounds, including a new dimeric diarylpropane, were isolated from the petroleum ether extract of the twigs and leaves of Horsfieldia tetratepala. The structures of these compounds were elucidated by spectroscopic analysis. Moreover, the antiproliferative activities of these compounds were tested on cancer cell lines, but none is active.
[Mh] Termos MeSH primário: Myristicaceae/química
Extratos Vegetais/química
Folhas de Planta/química
[Mh] Termos MeSH secundário: Antineoplásicos/isolamento & purificação
Antineoplásicos/farmacologia
Linhagem Celular Tumoral
Dimerização
Seres Humanos
Estrutura Molecular
Propano
Análise Espectral
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Plant Extracts); T75W9911L6 (Propane)
[Em] Mês de entrada:1802
[Cu] Atualização por classe:180228
[Lr] Data última revisão:
180228
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170624
[St] Status:MEDLINE
[do] DOI:10.1080/14786419.2017.1342087


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[PMID]:28581739
[Au] Autor:Kundu K; Nayak SK
[Ad] Endereço:Bio-Organic Division, Bhabha Atomic Research Centre , Trombay, Mumbai 400085, India.
[Ti] Título:Total Syntheses of Malabaricones B and C via a Cross-Metathesis Strategy.
[So] Source:J Nat Prod;80(6):1776-1782, 2017 Jun 23.
[Is] ISSN:1520-6025
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The malabaricones A-D belong to the class of diarylnonanoids isolated from the Myristicaceae family of plants. Although malabaricone C displayed various interesting biological activities, its isolation remains tedious due to its close chemical similarity to malabaricones A, B, and D. Therefore, development of an efficient synthesis route has become essential to cater to the need of large amounts of malabaricone C for its pharmacological profiling. So far there is only one report of the synthesis of malabaricone C through a lengthy sequence of reactions. We have developed an efficient and short route for the syntheses of malabaricones B and C, which will also provide a convenient access to all other members of the malabaricone family. Synthesis of an important building block, ω-aryl heptyl bromide, employed in the synthesis was realized by adopting a cross-metathesis reaction as the key step.
[Mh] Termos MeSH primário: Myristicaceae/química
Resorcinóis/síntese química
[Mh] Termos MeSH secundário: Relação Dose-Resposta a Droga
Estrutura Molecular
Ressonância Magnética Nuclear Biomolecular
Resorcinóis/química
Estereoisomerismo
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Resorcinols); 0 (malabaricone D); 63335-24-0 (malabaricone B); 63335-25-1 (malabaricone C)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170830
[Lr] Data última revisão:
170830
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170606
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jnatprod.6b01119


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[PMID]:28174103
[Au] Autor:Veiga A; Albuquerque K; Corrêa ME; Brigido H; Silva E Silva J; Campos M; Silveira F; Santos L; Dolabela M
[Ad] Endereço:Programa de Pós-Graduação em Inovação Farmacêutica, Instituto de Ciências da Saúde, Universidade Federal do Pará, Rua Augusto Corrêa, 01, 66075-110, Belém, Brazil. Electronic address: assv1977@gmail.com.
[Ti] Título:Leishmania amazonensis and Leishmania chagasi: In vitro leishmanicide activity of Virola surinamensis (rol.) warb.
[So] Source:Exp Parasitol;175:68-73, 2017 Apr.
[Is] ISSN:1090-2449
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Virola species have been used in traditional medicine as healing in skin infections. From V. surinanensis oil were isolated several sesquiterpene as the nerolidol which showed activity against species of Leishmania. The current study aimed to evaluate the leishmanicide activity and toxicity of extracts, fractions and surinamesin obtained from leaves of Virola surinamensis. Hexane, Ethyl Acetate, and Methanol extracts were obtained from powder of dry leaves of V. surinamensis. The hexane and ethyl acetate extracts were fractionated by silica gel column chromatography and increasingly polar gradient. The viability of L. chagasi and L. amazonensis promastigotes was assessed by tetrazolium salt assay (MTT). Peritoneal macrophages were exposed to L. amazonensis promastigotes. The treatment was performed with the extracts for 24 h. Then, the coverslips were stained and the infection index was determined. Cytotoxicity was determined in macrophage cells by peritoneum viability assay (MTT). The selectivity index was calculated as the product of cytotoxic concentration 50% and inhibitory concentration 50%. The hexane extract showed leishmanicide activity in promastigotes. The ethyl acetate, methanol extracts and fractions (C1-C6), were inactive against promastigote form of L. chagasi and L. amzazonensis. None extract showed effect on L. amazonensis amastigotes. All samples tested showed low cytotoxicity (CC > 500 µg/mL). The selectivity index of the hexane extract was greater than 5. The hexane extract of V. surinamensis was active against L. chagasi and L. amazonensis promastigotes. The extract fractionation did not increase significantly its antipromastigote activity. The surinamensin is probably not responsible for the activity. The extracts were inactive against amastigotes of L. amazonensis.
[Mh] Termos MeSH primário: Antiprotozoários/farmacologia
Leishmania infantum/efeitos dos fármacos
Leishmania mexicana/efeitos dos fármacos
Myristicaceae/química
Extratos Vegetais/farmacologia
[Mh] Termos MeSH secundário: Anisóis/química
Anisóis/isolamento & purificação
Anisóis/farmacologia
Antiprotozoários/química
Antiprotozoários/toxicidade
Concentração Inibidora 50
Lignanas/química
Lignanas/isolamento & purificação
Lignanas/farmacologia
Macrófagos Peritoneais/efeitos dos fármacos
Macrófagos Peritoneais/parasitologia
Espectroscopia de Ressonância Magnética
Extratos Vegetais/química
Extratos Vegetais/isolamento & purificação
Extratos Vegetais/toxicidade
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anisoles); 0 (Antiprotozoal Agents); 0 (Lignans); 0 (Plant Extracts); 0 (virolin); 68143-82-8 (surinamensin)
[Em] Mês de entrada:1703
[Cu] Atualização por classe:170328
[Lr] Data última revisão:
170328
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170209
[St] Status:MEDLINE


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[PMID]:27937036
[Au] Autor:Pereira AC; Lenz D; Nogueira BV; Scherer R; Andrade TU; Costa HB; Romão W; Pereira TM; Endringer DC
[Ad] Endereço:a Pharmaceutical Sciences Graduated Program, University Vila Velha , Vila Velha , Brazil.
[Ti] Título:Gastroprotective activity of the resin from Virola oleifera.
[So] Source:Pharm Biol;55(1):472-480, 2017 Dec.
[Is] ISSN:1744-5116
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:CONTEXT: The resin from the trunk wood of Virola oleifera (Schott) A. C. Smith (Myristicaceae) is used in folk medicine to hasten wound repair and to treat pain and inflammatory conditions, and our previous report indicated the anti-oxidative properties in other oxidative stress model. OBJECTIVE: To investigate the protective effects of resin from V. oleifera in two experimental models of gastric ulcer oxidative-stress dependent. MATERIALS AND METHODS: Plant material was collected and the resin was subjected to partitioning with organic solvents. The buthanol fraction was subjected to chromatographic and spectrometric methods for isolation and structural elucidation. The resin was quantified for polyphenols and flavonoids by colorimetric methods. Furthermore, the antioxidant activity of resin was determined by three different methods. The ulcers were induced acutely in Swiss male mice with ethanol/HCl and indomethacin using single-doses of 10 and 100 mg/kg. The gastroprotection of the experimental groups was comparable to reference control lansoprazole (3 mg/kg). RESULTS: The high content of polyphenols (∼82%) and the presence of epicatechin and eriodictyol were determined. The LD was estimated at 2500 mg/kg. At minimum (10 mg/kg) and maximum (100 mg/kg) dosage of resin, both in ethanol/HCl as indomethacin ulcer induction models demonstrate reduction of lesions (minimum: ∼97% and ∼66%; maximum: ∼95% and ∼59%). DISCUSSION: The gastroprotection might be related to tannins, phenolic acids and flavonoids present in the resin by antioxidant properties. CONCLUSIONS: The results indicate that this resin has gastroprotective activity probably associated with the presence of phenolic antioxidant substances.
[Mh] Termos MeSH primário: Antioxidantes/farmacologia
Mucosa Gástrica/efeitos dos fármacos
Myristicaceae/química
Extratos Vegetais/farmacologia
Resinas Vegetais/farmacologia
Úlcera Gástrica/prevenção & controle
[Mh] Termos MeSH secundário: Animais
Antiulcerosos/química
Antiulcerosos/isolamento & purificação
Antiulcerosos/farmacologia
Antiulcerosos/toxicidade
Antioxidantes/química
Antioxidantes/isolamento & purificação
Antioxidantes/toxicidade
Benzotiazóis/química
Cromatografia em Camada Delgada
Modelos Animais de Doenças
Etanol
Flavonoides/isolamento & purificação
Flavonoides/farmacologia
Mucosa Gástrica/patologia
Ácido Clorídrico
Indometacina
Dose Letal Mediana
Masculino
Camundongos
Fitoterapia
Casca de Planta
Extratos Vegetais/química
Extratos Vegetais/isolamento & purificação
Extratos Vegetais/toxicidade
Plantas Medicinais
Polifenóis/isolamento & purificação
Polifenóis/farmacologia
Resinas Vegetais/química
Resinas Vegetais/isolamento & purificação
Resinas Vegetais/toxicidade
Solventes/química
Espectrometria de Massas por Ionização por Electrospray
Úlcera Gástrica/induzido quimicamente
Úlcera Gástrica/patologia
Ácidos Sulfônicos/química
Espectrometria de Massas em Tandem
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-Ulcer Agents); 0 (Antioxidants); 0 (Benzothiazoles); 0 (Flavonoids); 0 (Plant Extracts); 0 (Polyphenols); 0 (Resins, Plant); 0 (Solvents); 0 (Sulfonic Acids); 28752-68-3 (2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid); 3K9958V90M (Ethanol); QTT17582CB (Hydrochloric Acid); XXE1CET956 (Indomethacin)
[Em] Mês de entrada:1703
[Cu] Atualização por classe:170313
[Lr] Data última revisão:
170313
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161213
[St] Status:MEDLINE


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[PMID]:27864261
[Au] Autor:Riba-Hernández P; Segura JL; Muñoz-Valverde J
[Ad] Endereço:Proyecto Carey, Península de Osa, Puntarenas, Costa Rica, Apdo. postal 10672-1000 San José, Costa Rica pabloribah@gmail.com.
[Ti] Título:Female fruit production depends on female flower production and crown size rather than male density in a continuous population of a tropical dioecious tree (Virola surinamensis).
[So] Source:Am J Bot;103(11):1990-1999, 2016 Nov.
[Is] ISSN:1537-2197
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:PREMISE OF THE STUDY: Factors related to pollen and resource limitation were evaluated to predict female fruit production in a tropical dioecious tree. Pollen limitation via variation in the male density at local scales is expected to limit female reproduction success in dioecious plants. METHODOLOGY: We modeled the roles of local male density, female crown size, crown illumination, and female flower production on female fruit initiation and mature fruit production in a continuous population (62 ha plot) of a tropical dioecious tree (Virola surinamensis). In addition, we used microsatellites to describe the scale of effective pollen flow, the male effective population size, and the spatial genetic structure within/between progenies and males. KEY RESULTS: The local male density was not related to female fruit initiation or mature fruit production. Female floral production had a positive effect on fruit initiation. The female crown size was positively related to fruit maturation. Seeds from the same female and seeds from different but spatially proximal females were generally half-siblings; however, proximal females showed greater variation. Proximal male-female adult pairs were not significantly more genetically related than distant pairs. The probability of paternity was negatively affected by the distance between seeds and males; most effective pollen dispersal events (∼85%) occurred from males located less than 150 m from females. The number of males siring progenies was greater than the number of males found at local scales. CONCLUSIONS: Female fecundity in this continuous population of Virola surinamensis is not limited by the availability of pollen from proximal males. Rather, resource allocation to floral production may ultimately determine female reproductive success.
[Mh] Termos MeSH primário: Flores/fisiologia
Myristicaceae/fisiologia
[Mh] Termos MeSH secundário: Demografia
Flores/genética
Flores/crescimento & desenvolvimento
Frutas/genética
Frutas/crescimento & desenvolvimento
Frutas/fisiologia
Geografia
Myristicaceae/genética
Myristicaceae/crescimento & desenvolvimento
Pólen/genética
Pólen/crescimento & desenvolvimento
Pólen/fisiologia
Polinização
Densidade Demográfica
Reprodução
Sementes/genética
Sementes/crescimento & desenvolvimento
Sementes/fisiologia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170515
[Lr] Data última revisão:
170515
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161120
[St] Status:MEDLINE


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[PMID]:27238085
[Au] Autor:Peng W; Yang C; Zhan R; Chen Y
[Ad] Endereço:a School of Chemistry and Chemical Engineering , Yunnan Normal University , Kunming , China.
[Ti] Título:Two new flavans from the trunk and leaves of Horsfieldia glabra.
[So] Source:Nat Prod Res;30(20):2350-5, 2016 Oct.
[Is] ISSN:1478-6427
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Two new flavans, (2R, 4R)-4'-hydroxy-3',5'-methyl-6,7-methylenedioxy-4-O-2'-cycloflavan (1), and (2R, 4R)-4'-hydroxy-3'-methyl-6,7-methylenedioxy-4-O-2'-cycloflavan (2), along with six known compounds were isolated from the trunk and leaves of Horsfieldia glabra. Their structures were elucidated by means of extensive spectroscopic analysis. Compounds 1 and 2, together with 4-7 were assessed for their cytotoxicity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that they had no activity.
[Mh] Termos MeSH primário: Benzopiranos/isolamento & purificação
Flavonoides/isolamento & purificação
Myristicaceae/química
[Mh] Termos MeSH secundário: Benzopiranos/química
Morte Celular/efeitos dos fármacos
Linhagem Celular Tumoral
Flavonoides/química
Flavonoides/farmacologia
Células HL-60
Seres Humanos
Estrutura Molecular
Folhas de Planta/química
Análise Espectral
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Benzopyrans); 0 (Flavonoids)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170817
[Lr] Data última revisão:
170817
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160531
[St] Status:MEDLINE
[do] DOI:10.1080/14786419.2016.1185719


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[PMID]:27236720
[Au] Autor:Abdul Wahab SM; Sivasothy Y; Liew SY; Litaudon M; Mohamad J; Awang K
[Ad] Endereço:Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia.
[Ti] Título:Natural cholinesterase inhibitors from Myristica cinnamomea King.
[So] Source:Bioorg Med Chem Lett;26(15):3785-92, 2016 08 01.
[Is] ISSN:1464-3405
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A new acylphenol, malabaricone E (1) together with the known malabaricones A-C (2-4), maingayones A and B (5 and 6) and maingayic acid B (7) were isolated from the ethyl acetate extract of the fruits of Myristica cinnamomea King. Their structures were determined by 1D and 2D NMR techniques and LCMS-IT-TOF analysis. Compounds 3 (1.84±0.19 and 1.76±0.21µM, respectively) and 4 (1.94±0.27 and 2.80±0.49µM, respectively) were identified as dual inhibitors, with almost equal acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes inhibiting potentials. The Lineweaver-Burk plots of compounds 3 and 4 indicated that they were mixed-mode inhibitors. Based on the molecular docking studies, compounds 3 and 4 interacted with the peripheral anionic site (PAS), the catalytic triad and the oxyanion hole of the AChE. As for the BChE, while compound 3 interacted with the PAS, the catalytic triad and the oxyanion hole, compound 4 only interacted with the catalytic triad and the oxyanion hole.
[Mh] Termos MeSH primário: Acetilcolinesterase/metabolismo
Produtos Biológicos/farmacologia
Butirilcolinesterase/metabolismo
Inibidores da Colinesterase/farmacologia
Myristicaceae/química
[Mh] Termos MeSH secundário: Animais
Produtos Biológicos/química
Produtos Biológicos/isolamento & purificação
Inibidores da Colinesterase/química
Inibidores da Colinesterase/isolamento & purificação
Relação Dose-Resposta a Droga
Seres Humanos
Simulação de Acoplamento Molecular
Estrutura Molecular
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Biological Products); 0 (Cholinesterase Inhibitors); EC 3.1.1.7 (Acetylcholinesterase); EC 3.1.1.8 (Butyrylcholinesterase)
[Em] Mês de entrada:1706
[Cu] Atualização por classe:171122
[Lr] Data última revisão:
171122
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160530
[St] Status:MEDLINE


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[PMID]:27102164
[Au] Autor:Sivasothy Y; Krishnan T; Chan KG; Abdul Wahab SM; Othman MA; Litaudon M; Awang K
[Ad] Endereço:Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia. yasodhasivasothy@gmail.com.
[Ti] Título:Quorum Sensing Inhibitory Activity of Giganteone A from Myristica cinnamomea King against Escherichia coli Biosensors.
[So] Source:Molecules;21(3):391, 2016 Mar 21.
[Is] ISSN:1420-3049
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Malabaricones A-C (1-3) and giganteone A (4) were isolated from the bark of Myristica cinnamomea King. Their structures were elucidated and characterized by means of NMR and MS spectral analyses. These isolates were evaluated for their anti-quorum sensing activity using quorum sensing biosensors, namely Escherichia coli [pSB401] and Escherichia coli [pSB1075], whereby the potential of giganteone A (4) as a suitable anti-quorum sensing agent was demonstrated.
[Mh] Termos MeSH primário: Antibacterianos/farmacologia
Técnicas Biossensoriais
Compostos de Bifenilo/farmacologia
Percepção de Quorum/efeitos dos fármacos
Resorcinóis/farmacologia
[Mh] Termos MeSH secundário: Antibacterianos/química
Antibacterianos/isolamento & purificação
Compostos de Bifenilo/química
Escherichia coli/efeitos dos fármacos
Escherichia coli/patogenicidade
Seres Humanos
Myristicaceae/química
Pseudomonas aeruginosa/efeitos dos fármacos
Pseudomonas aeruginosa/patogenicidade
Resorcinóis/química
Resorcinóis/isolamento & purificação
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 0 (Biphenyl Compounds); 0 (Resorcinols); 0 (giganteone A); 0 (malabaricone A)
[Em] Mês de entrada:1612
[Cu] Atualização por classe:161230
[Lr] Data última revisão:
161230
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160423
[St] Status:MEDLINE


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[PMID]:27072985
[Au] Autor:Othman MA; Sivasothy Y; Looi CY; Ablat A; Mohamad J; Litaudon M; Awang K
[Ad] Endereço:Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia.
[Ti] Título:Acylphenols and dimeric acylphenols from Myristica maxima Warb.
[So] Source:Fitoterapia;111:12-7, 2016 Jun.
[Is] ISSN:1873-6971
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Giganteone E (1), a new dimeric acylphenol was isolated as a minor constituent from the bark of Myristica maxima Warb. The structure of 1 was established on the basis of 1D and 2D NMR techniques and LCMS-IT-TOF analysis. Malabaricones A-C (2-4), giganteones A and C (5 and 6), maingayones A and B (7 and 8), maingayic acid B (9) and ß-sitosteryl oleate (10) were also characterized in this plant for the first time. Compound 10 was identified for the first time in the Myristicaceae. Compounds 2 and 5 were active against human prostate cancer cell-lines, thus making this the first report on the prostate cancer inhibiting potential of acylphenols and dimeric acylphenols. Compounds 1, 4, 5, 7 and 8 exhibited potent DPPH free radical scavenging activity. This is the first report on their free radical scavenging capacity.
[Mh] Termos MeSH primário: Myristicaceae/química
Fenóis/farmacologia
[Mh] Termos MeSH secundário: Antineoplásicos Fitogênicos/isolamento & purificação
Antineoplásicos Fitogênicos/farmacologia
Linhagem Celular Tumoral/efeitos dos fármacos
Depuradores de Radicais Livres/isolamento & purificação
Depuradores de Radicais Livres/farmacologia
Seres Humanos
Masculino
Estrutura Molecular
Fenóis/isolamento & purificação
Neoplasias da Próstata/patologia
Resorcinóis/isolamento & purificação
Resorcinóis/farmacologia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents, Phytogenic); 0 (Free Radical Scavengers); 0 (Phenols); 0 (Resorcinols); 0 (giganteone E); 0 (malabaricone A); 63335-24-0 (malabaricone B); 63335-25-1 (malabaricone C)
[Em] Mês de entrada:1701
[Cu] Atualização por classe:170117
[Lr] Data última revisão:
170117
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160414
[St] Status:MEDLINE


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[PMID]:27008174
[Au] Autor:Gény C; Rivière G; Bignon J; Birlirakis N; Guittet E; Awang K; Litaudon M; Roussi F; Dumontet V
[Ad] Endereço:Institut de Chimie des Substances Naturelles, CNRS-ICSN UPR2301, Université Paris-Saclay , Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
[Ti] Título:Anacardic Acids from Knema hookeriana as Modulators of Bcl-xL/Bak and Mcl-1/Bid Interactions.
[So] Source:J Nat Prod;79(4):838-44, 2016 Apr 22.
[Is] ISSN:1520-6025
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Proteins of the Bcl-2 family are key targets in anticancer drug discovery. Disrupting the interaction between anti- and pro-apoptotic members of this protein family was the approach chosen in this study to restore apoptosis. Thus, a biological screening on the modulation of the Bcl-xL/Bak and Mcl-1/Bid interactions permitted the selection of Knema hookeriana for further phytochemical investigations. The ethyl acetate extract from the stem bark led to the isolation of six new compounds, three acetophenone derivatives (1-3) and three anacardic acid derivatives (4-6), along with four known anacardic acids (7-10) and two cardanols (11, 12). Their structures were elucidated by 1D and 2D NMR analysis in combination with HRMS experiments. The ability of these compounds to antagonize Bcl-xL/Bak and Mcl-1/Bid association was determined, using a protein-protein interaction assay, but only anacardic acid derivatives (4-10) exhibited significant binding properties, with Ki values ranging from 0.2 to 18 µM. Protein-ligand NMR experiments further revealed that anacardic acid 9, the most active compound, does not interact with the anti-apoptotic proteins Bcl-xL and Mcl-1 but instead interacts with pro-apoptotic protein Bid.
[Mh] Termos MeSH primário: Acetofenonas/isolamento & purificação
Ácidos Anacárdicos/isolamento & purificação
Ácidos Anacárdicos/farmacologia
Myristicaceae/química
Proteínas Proto-Oncogênicas c-bcl-2/metabolismo
Resorcinóis/isolamento & purificação
[Mh] Termos MeSH secundário: Acetofenonas/química
Acetofenonas/farmacologia
Ácidos Anacárdicos/química
Apoptose/efeitos dos fármacos
Proteínas Reguladoras de Apoptose/metabolismo
Proteína Agonista de Morte Celular de Domínio Interatuante com BH3/efeitos dos fármacos
Malásia
Estrutura Molecular
Ressonância Magnética Nuclear Biomolecular
Casca de Planta/química
Proteínas Proto-Oncogênicas c-bcl-2/efeitos dos fármacos
Resorcinóis/química
Resorcinóis/farmacologia
Proteína Killer-Antagonista Homóloga a bcl-2/efeitos dos fármacos
Proteína bcl-X/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Acetophenones); 0 (Anacardic Acids); 0 (Apoptosis Regulatory Proteins); 0 (BH3 Interacting Domain Death Agonist Protein); 0 (Proto-Oncogene Proteins c-bcl-2); 0 (Resorcinols); 0 (bcl-2 Homologous Antagonist-Killer Protein); 0 (bcl-X Protein); UC3V356VZC (resacetophenone)
[Em] Mês de entrada:1609
[Cu] Atualização por classe:160422
[Lr] Data última revisão:
160422
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160324
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jnatprod.5b00915



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