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Pesquisa : D02.455.849.919.490 [Categoria DeCS]
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[PMID]:29185131
[Au] Autor:Alshammari GM; Balakrishnan A; Chinnasamy T
[Ad] Endereço:Department of Food Science and Nutrition, College of Food and Agricultural Science, King Saud University, P.O. Box 2460, Riyadh, 11451, Saudi Arabia. ghedeirksu@gmail.com.
[Ti] Título:Nimbolide attenuate the lipid accumulation, oxidative stress and antioxidant in primary hepatocytes.
[So] Source:Mol Biol Rep;44(6):463-474, 2017 Dec.
[Is] ISSN:1573-4978
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Nimbolide is a bioactive compound found in Azadirachta indica. This work was devised to investigate the potential effects of nimbolide on intracellular lipid deposition and its associated redox modulation in primary hepatocytes (Heps). Lipid accumulation was induced in Heps by supplementing 1 mM oleic acid for 24 h which was marked by significant accumulation of lipids. The results demonstrated that nimbolide can decrease intracellular cholesterol, free fatty acids and triglycerides. Nimbolide may also improve hepatocytes function through its antioxidant effects by inhibiting oxidative DNA damage and lipid peroxidation by curtailing the reactive oxygen species levels. Further it also restore the mitochondrial potential, improving the endogenous antioxidant levels such as GSH and antioxidant enzyme activities. Nimbolide increased (P < 0.05) liver X receptor-α (LXRα), peroxisome proliferator-activated receptor-γ (PPARγ) and sterol regulatory element-binding protein-1c (SREBP1c) gene expression in Heps. The biological significance of nimbolide may involve hypolipidemic effect, lipid peroxidation inhibition, DNA damage inhibition, ROS inhibition, restoring mitochondrial function, increases in GSH and SOD & CAT activities, and direct regulation of LXRα, PPARγ and SREBP1c gene expression. Nimbolide may be used as effective lipid lowering compound and lipid deposition-induced Heps changes.
[Mh] Termos MeSH primário: Hepatócitos/efeitos dos fármacos
Hepatócitos/metabolismo
Limoninas/farmacologia
Metabolismo dos Lipídeos/efeitos dos fármacos
[Mh] Termos MeSH secundário: Animais
Antioxidantes/farmacologia
Células Cultivadas
Seres Humanos
Hipolipemiantes/farmacologia
Peroxidação de Lipídeos/efeitos dos fármacos
Receptores X do Fígado/metabolismo
Oxirredução/efeitos dos fármacos
Estresse Oxidativo/efeitos dos fármacos
PPAR gama/metabolismo
Espécies Reativas de Oxigênio/metabolismo
Triglicerídeos/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antioxidants); 0 (Hypolipidemic Agents); 0 (Limonins); 0 (Liver X Receptors); 0 (PPAR gamma); 0 (Reactive Oxygen Species); 0 (Triglycerides); 25990-37-8 (nimbolide)
[Em] Mês de entrada:1801
[Cu] Atualização por classe:180102
[Lr] Data última revisão:
180102
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:171130
[St] Status:MEDLINE
[do] DOI:10.1007/s11033-017-4132-1


  2 / 933 MEDLINE  
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[PMID]:29107110
[Au] Autor:Kumar S; Inigo JR; Kumar R; Chaudhary AK; O'Malley J; Balachandar S; Wang J; Attwood K; Yadav N; Hochwald S; Wang X; Chandra D
[Ad] Endereço:Department of Pharmacology and Therapeutics, Center for Genetics and Pharmacology, Roswell Park Cancer Institute, Elm & Carlton Streets, Buffalo, NY 14263, USA.
[Ti] Título:Nimbolide reduces CD44 positive cell population and induces mitochondrial apoptosis in pancreatic cancer cells.
[So] Source:Cancer Lett;413:82-93, 2018 Jan 28.
[Is] ISSN:1872-7980
[Cp] País de publicação:Ireland
[La] Idioma:eng
[Ab] Resumo:Pancreatic ductal adenocarcinoma (PDAC) is highly aggressive disease and current treatment regimens fail to effectively cure PDAC. Development of resistance to current therapy is one of the key reasons for this outcome. Nimbolide (NL), a triterpenoid obtained from Azadirachta indica, exhibits anticancer properties in various cancer including PDAC cells. However, the underlying mechanism of this anticancer agent in PDAC cells remains undefined. We show that NL exerts a higher level of apoptotic cell death compared to the first-line agent gemcitabine for PDAC, as well as other anticancer agents including sorafenib and curcumin. The anticancer efficacy of NL was further evidenced by a reduction in the CD44 as well as cancer stem-like cell (CSC) population, as it causes decreased sphere formation. Mechanistically, the anticancer efficacy of NL associates with reduced mutant p53 as well as increased mitochondrial activity in the form of increased mitochondrial reactive oxygen species and mitochondrial mass. Together, this study highlights the therapeutic potential of NL in mutant p53 expressing pancreatic cancer.
[Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/farmacologia
Apoptose/efeitos dos fármacos
Carcinoma Ductal Pancreático/tratamento farmacológico
Inibidores de Caspase/farmacologia
Receptores de Hialuronatos/metabolismo
Limoninas/farmacologia
Mitocôndrias/efeitos dos fármacos
Células-Tronco Neoplásicas/efeitos dos fármacos
Neoplasias Pancreáticas/tratamento farmacológico
[Mh] Termos MeSH secundário: Carcinoma Ductal Pancreático/genética
Carcinoma Ductal Pancreático/metabolismo
Carcinoma Ductal Pancreático/patologia
Linhagem Celular Tumoral
Movimento Celular/efeitos dos fármacos
Desoxicitidina/análogos & derivados
Desoxicitidina/farmacologia
Relação Dose-Resposta a Droga
Seres Humanos
Mitocôndrias/metabolismo
Mitocôndrias/patologia
Mutação
Células-Tronco Neoplásicas/metabolismo
Células-Tronco Neoplásicas/patologia
Neoplasias Pancreáticas/genética
Neoplasias Pancreáticas/metabolismo
Neoplasias Pancreáticas/patologia
Espécies Reativas de Oxigênio/metabolismo
Fatores de Tempo
Proteína Supressora de Tumor p53/genética
Proteína Supressora de Tumor p53/metabolismo
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents, Phytogenic); 0 (CD44 protein, human); 0 (Caspase Inhibitors); 0 (Hyaluronan Receptors); 0 (Limonins); 0 (Reactive Oxygen Species); 0 (TP53 protein, human); 0 (Tumor Suppressor Protein p53); 0W860991D6 (Deoxycytidine); 25990-37-8 (nimbolide); B76N6SBZ8R (gemcitabine)
[Em] Mês de entrada:1712
[Cu] Atualização por classe:171219
[Lr] Data última revisão:
171219
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:171107
[St] Status:MEDLINE


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[PMID]:28864040
[Au] Autor:Dai YG; Wu J; Padmakumar KP; Shen L
[Ad] Endereço:Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, PR China.
[Ti] Título:Sundarbanxylogranins A-E, five new limonoids from the Sundarban Mangrove, Xylocarpus granatum.
[So] Source:Fitoterapia;122:85-89, 2017 Oct.
[Is] ISSN:1873-6971
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Five new limonoids, named sundarbanxylogranins A-E (1-5), were isolated from the seeds of an Indian mangrove, Xylocarpus granatum, collected from mangrove swamps of the Sundarbans, India. The structures of these limonoids were established by HRESIMS and NMR spectroscopic data. Sundarbanxylogranin A (1) is a rare limonoid containing a bicyclo[5.2.1]dec-3-en-8-one scaffold as the ring A/B-fused core; whereas sundarbanxylogranin B (2) is a typical mexicanolide with an 8α, 30α-epoxy ring. Sundarbanxylogranins C-E (3-5), among which the former two possess a 29-OMe group with different orientation, belong to a small group of limonoids containing a C -O-C oxygen bridge. Sundarbanxylogranin B exhibited moderate anti-HIV activity with an IC value of 23.14±1.29µM and a CC value of 78.45±1.69µM, respectively.
[Mh] Termos MeSH primário: Limoninas/farmacologia
Meliaceae/química
Sementes/química
[Mh] Termos MeSH secundário: Fármacos Anti-HIV/isolamento & purificação
Fármacos Anti-HIV/farmacologia
Células HEK293
HIV-1/efeitos dos fármacos
Seres Humanos
Índia
Limoninas/isolamento & purificação
Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-HIV Agents); 0 (Limonins); 0 (mexicanolide)
[Em] Mês de entrada:1711
[Cu] Atualização por classe:171103
[Lr] Data última revisão:
171103
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170903
[St] Status:MEDLINE


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[PMID]:28829608
[Au] Autor:Wu YB; Wang YZ; Ni ZY; Qing X; Shi QW; Sauriol F; Vavricka CJ; Gu YC; Kiyota H
[Ti] Título:Xylomexicanins I and J: Limonoids with Unusual B/C Rings from Xylocarpus granatum.
[So] Source:J Nat Prod;80(9):2547-2550, 2017 Sep 22.
[Is] ISSN:1520-6025
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Two tetranortriterpenoids with new skeletons, xylomexicanins I and J (1 and 2), were isolated during the investigation of chemical constituents from seeds of the Chinese mangrove, Xylocarpus granatum. Xylomexicanin I (1) is an unprecedented limonoid with bridged B- and C-rings. A biosynthesis pathway for 1 from xylomexicanin F is proposed.
[Mh] Termos MeSH primário: Limoninas/isolamento & purificação
Meliaceae/química
Sementes/química
[Mh] Termos MeSH secundário: Limoninas/química
Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Limonins); 0 (xylomexicanin F); 0 (xylomexicanin I); 0 (xylomexicanin J)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171031
[Lr] Data última revisão:
171031
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170823
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jnatprod.7b00305


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[PMID]:28673807
[Au] Autor:Geng YD; Zhang C; Lei JL; Yu P; Xia YZ; Zhang H; Yang L; Kong LY
[Ad] Endereço:Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China.
[Ti] Título:Walsuronoid B induces mitochondrial and lysosomal dysfunction leading to apoptotic rather than autophagic cell death via ROS/p53 signaling pathways in liver cancer.
[So] Source:Biochem Pharmacol;142:71-86, 2017 Oct 15.
[Is] ISSN:1873-2968
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Walsuronoid B is a limonoid compound extracted from Walsura robusta. Previous studies have shown that limonoid compounds possess anti-cancer potential, although the molecular mechanism of this activity remains elusive. In this study, we demonstrated for the first time that walsuronoid B inhibited cell proliferation in several human cancer lines. Liver cancer cells (HepG2 and Bel-7402) were chosen for their high sensitivity to walsuronoid B. Walsuronoid B induced cell death through G /M phase arrest and apoptosis and induced the accumulation of autophagosomes through the suppression of mTOR signaling, which serves as a cell survival mechanism and prevents cell death. We further examined the molecular mechanisms and found that walsuronoid B-induced dysfunction of the mitochondria and lysosomes rather than the endoplasmic reticulum contributed to its cell death effect. Walsuronoid B enhanced the generation of hydrogen peroxide, nitric oxide and superoxide anion radical, resulting in elevated levels of reactive oxygen species (ROS). In addition, ROS induced by walsuronoid B upregulated p53 levels; conversely, p53 stimulated ROS. These results suggested that ROS and p53 reciprocally promoted each other's production and cooperated to induce liver cancer cell death. We found that the induction of ROS and p53 significantly triggered G /M phase arrest and mitochondrial and lysosomal apoptosis. Finally, walsuronoid B suppressed tumor growth in vivo with few side effects. In summary, our findings demonstrated that walsuronoid B caused G /M phase arrest and induced mitochondrial and lysosomal apoptosis through the ROS/p53 signaling pathway in human liver cancer cells in vitro and in vivo.
[Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/farmacologia
Apoptose/efeitos dos fármacos
Hidrocarbonetos Aromáticos com Pontes/farmacologia
Limoninas/farmacologia
Neoplasias Hepáticas
Lisossomos/metabolismo
Potencial da Membrana Mitocondrial/efeitos dos fármacos
Espécies Reativas de Oxigênio/metabolismo
Proteína Supressora de Tumor p53/metabolismo
[Mh] Termos MeSH secundário: Animais
Antineoplásicos Fitogênicos/isolamento & purificação
Antineoplásicos Fitogênicos/uso terapêutico
Autofagia/efeitos dos fármacos
Hidrocarbonetos Aromáticos com Pontes/isolamento & purificação
Hidrocarbonetos Aromáticos com Pontes/uso terapêutico
Pontos de Checagem do Ciclo Celular/efeitos dos fármacos
Proliferação Celular/efeitos dos fármacos
Sobrevivência Celular/efeitos dos fármacos
Relação Dose-Resposta a Droga
Células Hep G2
Seres Humanos
Limoninas/isolamento & purificação
Limoninas/uso terapêutico
Neoplasias Hepáticas/metabolismo
Neoplasias Hepáticas/patologia
Neoplasias Hepáticas Experimentais/tratamento farmacológico
Neoplasias Hepáticas Experimentais/metabolismo
Neoplasias Hepáticas Experimentais/patologia
Lisossomos/fisiologia
Meliaceae/química
Camundongos Endogâmicos BALB C
Camundongos Nus
Transdução de Sinais
Ensaios Antitumorais Modelo de Xenoenxerto
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents, Phytogenic); 0 (Bridged-Ring Compounds); 0 (Limonins); 0 (Reactive Oxygen Species); 0 (Tumor Suppressor Protein p53); 0 (walsuronoid B)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171017
[Lr] Data última revisão:
171017
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170705
[St] Status:MEDLINE


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[PMID]:28622618
[Au] Autor:Yang YF; Zhang LZ; Du XP; Zhang SF; Li LJ; Jiang ZD; Wu LM; Ni H; Chen F
[Ad] Endereço:College of Food and Biology Engineering, Jimei University, Xiamen, Fujian Province 361021, China; Fujian Provincial Key Laboratory of Food Microbiology and Enzyme Engineering Technology, Xiamen, Fujian Province 361021, China; Research Center of Food Biotechnology of Xiamen City, Xiamen, Fujian Provi
[Ti] Título:Recovery and purification of limonin from pummelo [Citrus grandis] peel using water extraction, ammonium sulfate precipitation and resin adsorption.
[So] Source:J Chromatogr B Analyt Technol Biomed Life Sci;1060:150-157, 2017 Aug 15.
[Is] ISSN:1873-376X
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Limonin is a bioactive compound that is traditionally extracted from citrus seeds using organic solvents or alkaline/metal ion solutions. In the present study, pummelo [Citrus grandis] peel was investigated for limonin preparation using a novel process consisting of water extraction, ammonium sulfate precipitation and resin adsorption. The pummelo peel was determined to have 4.7mg/g limonin, which could be extracted by water and further recovered by ammonium sulfate precipitation with a yield of 2.4mg/g, which was similar to that of traditional process using ethanol extraction and vacuumed evaporation. The precipitated limonin was purified by resin adsorption and crystallization with a purity of 96.4%. In addition, the limonin was identified via the analyses of retention time, infrared spectrum and nuclear magnetic resonance. This study indicates a novel and eco-friendly process for recovering limonin, providing a new candidate for limonin preparation.
[Mh] Termos MeSH primário: Sulfato de Amônio/química
Citrus/química
Limoninas/análise
Limoninas/isolamento & purificação
[Mh] Termos MeSH secundário: Adsorção
Precipitação Química
Cromatografia Líquida de Alta Pressão
Limoninas/química
Espectroscopia de Ressonância Magnética
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Limonins); L0F260866S (limonin); SU46BAM238 (Ammonium Sulfate)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170915
[Lr] Data última revisão:
170915
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170617
[St] Status:MEDLINE


  7 / 933 MEDLINE  
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[PMID]:28594916
[Au] Autor:Sasaki T; Mita M; Ikari N; Kuboyama A; Hashimoto S; Kaneko T; Ishiguro M; Shimizu M; Inoue J; Sato R
[Ad] Endereço:Food Biochemistry Laboratory, Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, University of Tokyo, Tokyo, Japan.
[Ti] Título:Identification of key amino acid residues in the hTGR5-nomilin interaction and construction of its binding model.
[So] Source:PLoS One;12(6):e0179226, 2017.
[Is] ISSN:1932-6203
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:TGR5, a member of the G protein-coupled receptor (GPCR) family, is activated by bile acids. Because TGR5 promotes energy expenditure and improves glucose homeostasis, it is recognized as a key target in treating metabolic diseases. We previously showed that nomilin, a citrus limonoid, activates TGR5 and confers anti-obesity and anti-hyperglycemic effects in mice. Information on the TGR5-nomilin interaction regarding molecular structure, however, has not been reported. In the present study, we found that human TGR5 (hTGR5) shows higher nomilin responsiveness than does mouse TGR5 (mTGR5). Using mouse-human chimeric TGR5, we also found that three amino acid residues (Q77ECL1, R80ECL1, and Y893.29) are important in the hTGR5-nomilin interaction. Based on these results, an hTGR5-nomilin binding model was constructed using in silico docking simulation, demonstrating that four hydrophilic hydrogen-bonding interactions occur between nomilin and hTGR5. The binding mode of hTGR5-nomilin is vastly different from those of other TGR5 agonists previously reported, suggesting that TGR5 forms various binding patterns depending on the type of agonist. Our study promotes a better understanding of the structure of TGR5, and it may be useful in developing and screening new TGR5 agonists.
[Mh] Termos MeSH primário: Aminoácidos/química
Benzoxepinas/química
Benzoxepinas/metabolismo
Limoninas/química
Limoninas/metabolismo
Modelos Moleculares
Receptores Acoplados a Proteínas-G/química
Receptores Acoplados a Proteínas-G/metabolismo
[Mh] Termos MeSH secundário: Sequência de Aminoácidos
Animais
Células HEK293
Seres Humanos
Camundongos
Simulação de Acoplamento Molecular
Mutação/genética
Especificidade por Substrato
Ácido Taurolitocólico/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Amino Acids); 0 (Benzoxepins); 0 (GPBAR1 protein, human); 0 (Limonins); 0 (Receptors, G-Protein-Coupled); 516-90-5 (Taurolithocholic Acid); 751-03-1 (obacunone); DRM0753K4T (nomilin)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170918
[Lr] Data última revisão:
170918
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170609
[St] Status:MEDLINE
[do] DOI:10.1371/journal.pone.0179226


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[PMID]:28505282
[Au] Autor:Freitas CD; Gontijo LM; Guedes RNC; Chediak M
[Ad] Endereço:Programa de Manejo e Conservação de Ecossistemas Naturais e Agrários, Universidade Federal de Viçosa - Campus Florestal, Florestal, MG 35690-000, Brazil.
[Ti] Título:Survival and Locomotory Behavior of Earwigs After Exposure to Reduced-Risk Insecticides.
[So] Source:J Econ Entomol;110(4):1576-1582, 2017 Aug 01.
[Is] ISSN:1938-291X
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The conservation of natural enemies is an important tactic to promote biological control of arthropod pests. The earwig Doru luteipes (Sccuder) is the most important predator of the fall armyworm Spodoptera frugiperda (J.E. Smith) in corn fields. One way of conserving these predators in the field is by using only selective insecticides when the pest population reaches the economic threshold. Some recent insecticides such as azadirachtin, chlorantraniliprole, and novaluron have been claimed to pose reduced risk for natural enemies. Nevertheless, there is a dearth of information regarding the selectivity of these insecticides upon earwigs in specific. In this study, we carried out a series of laboratory assays to examine the survivorship and locomotory behavior of D. luteipes after exposure to fresh dry residue of azadirachtin, chlorantraniliprole, and novaluron. Our results show a significant survival reduction for D. luteipes nymphs exposed to fresh residues of chlorantraniliprole and novaluron. In the behavioral studies, adults of D. luteipes stopped more often, spent more time resting (inactive), and moved more slowly immediately after exposure to chlorantraniliprole residue. These results suggest that chlorantraniliprole may mediate an impaired movement and a behavior arrestment of earwigs after contact with this insecticide fresh residue. This could translate into reduced foraging efficiency, and increase exposure and insecticide uptake. Although chlorantraniliprole and novaluron showed a potential to undermine the biological control provided by earwigs, it is yet essential to conduct field trials in order to confirm our laboratory results.
[Mh] Termos MeSH primário: Insetos/efeitos dos fármacos
Inseticidas/toxicidade
Resíduos de Praguicidas/toxicidade
Comportamento Predatório/efeitos dos fármacos
[Mh] Termos MeSH secundário: Animais
Feminino
Insetos/crescimento & desenvolvimento
Insetos/fisiologia
Limoninas/toxicidade
Locomoção/efeitos dos fármacos
Longevidade/efeitos dos fármacos
Masculino
Ninfa/efeitos dos fármacos
Ninfa/crescimento & desenvolvimento
Ninfa/fisiologia
Compostos de Fenilureia/toxicidade
ortoaminobenzoatos/toxicidade
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Insecticides); 0 (Limonins); 0 (Pesticide Residues); 0 (Phenylurea Compounds); 0 (ortho-Aminobenzoates); 622AK9DH9G (chlorantranilipole); O4U1SAF85H (azadirachtin); Z8H1B3CW0B (novaluron)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170516
[St] Status:MEDLINE
[do] DOI:10.1093/jee/tox137


  9 / 933 MEDLINE  
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[PMID]:28425165
[Au] Autor:Akihisa T; Yokokawa S; Ogihara E; Matsumoto M; Zhang J; Kikuchi T; Koike K; Abe M
[Ad] Endereço:Research Institute for Science & Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan.
[Ti] Título:Melanogenesis-Inhibitory and Cytotoxic Activities of Limonoids, Alkaloids, and Phenolic Compounds from Phellodendron amurense Bark.
[So] Source:Chem Biodivers;14(7), 2017 Jul.
[Is] ISSN:1612-1880
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Four limonoids, 1 - 4, five alkaloids, 5 - 9, and four phenolic compounds, 10 - 13, were isolated from a MeOH extract of the bark of Phellodendron amurense (Rutaceae). Among these, compound 13 was new, and its structure was established as rel-(1R,2R,3R)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1-(methoxycarbonylmethyl)indane-2-carboxylic acid methyl ester (γ-di(methyl ferulate)) based on the spectrometric analysis. Upon evaluation of compounds 1 - 13 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), four compounds, limonin (1), noroxyhydrastinine (6), haplopine (7), and 4-methoxy-1-methylquinolin-2(1H)-one (8), exhibited potent melanogenesis-inhibitory activities with almost no toxicity to the cells. Western blot analysis revealed that compound 6 inhibited melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP-1, and TRP-2 in α-MSH-stimulated B16 melanoma cells. In addition, when compounds 1 - 13 were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), duodenum (AZ521), and breast (SK-BR-3) cancer cell lines, five compounds, berberine (5), 8, canthin-6-one (9), α-di-(methyl ferulate) (12), and 13, exhibited cytotoxicities against one or more cancer cell lines with IC values in the range of 2.6 - 90.0 µm. In particular, compound 5 exhibited strong cytotoxicity against AZ521 (IC 2.6 µm) which was superior to that of the reference cisplatin (IC 9.5 µm).
[Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/isolamento & purificação
Phellodendron/química
[Mh] Termos MeSH secundário: Alcaloides/isolamento & purificação
Alcaloides/farmacologia
Antineoplásicos Fitogênicos/química
Antineoplásicos Fitogênicos/farmacologia
Carcinogênese
Linhagem Celular Tumoral
Seres Humanos
Concentração Inibidora 50
Limoninas/isolamento & purificação
Limoninas/farmacologia
Melanoma Experimental/patologia
Metanol
Fenóis/isolamento & purificação
Fenóis/farmacologia
Casca de Planta/química
Extratos Vegetais
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Alkaloids); 0 (Antineoplastic Agents, Phytogenic); 0 (Limonins); 0 (Phenols); 0 (Plant Extracts); Y4S76JWI15 (Methanol)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170922
[Lr] Data última revisão:
170922
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170421
[St] Status:MEDLINE
[do] DOI:10.1002/cbdv.201700105


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[PMID]:28419927
[Au] Autor:Ashok Yadav P; Pavan Kumar C; Siva B; Suresh Babu K; Allanki AD; Sijwali PS; Jain N; Veerabhadra Rao A
[Ad] Endereço:Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
[Ti] Título:Synthesis and evaluation of anti-plasmodial and cytotoxic activities of epoxyazadiradione derivatives.
[So] Source:Eur J Med Chem;134:242-257, 2017 Jul 07.
[Is] ISSN:1768-3254
[Cp] País de publicação:France
[La] Idioma:eng
[Ab] Resumo:Epoxyazadiradione (1), a major compound derived from Neem oil, showed modest anti-plasmodial activity against CQ-resistant and CQ-sensitive strains of the most virulent human malaria parasite P. falciparum. A series of analogues were synthesized by modification of the key structural moieties of this high yield natural product. Out of the library of all compounds tested, compounds 3c and 3g have showed modest anti-plasmodial activity against CQ-sensitive (IC 2.8 ± 0.29 µM and 1.5 ± 0.01 µM) and CQ-resistant strains (IC 1.3 ± 1.08 µM and 1.2 ± 0.14), while compounds 3k, 3l and 3m showed modest activity against CQ-sensitive strain of P. falciparum with IC values of 2.3 ± 0.4 µM, 2.9 ± 0.1 µM and 1.7 ± 0.06 µM, respectively. Additionally, cytotoxic properties of these derivatives against SIHA, PANC 1, MDA-MB-231, and IMR-3 cancer cell lines were also studied and the results indicated that low cytotoxic potentials of all the derivatives which indicating the high selectivity index of the compounds.
[Mh] Termos MeSH primário: Antimaláricos/química
Antimaláricos/farmacologia
Antineoplásicos/química
Antineoplásicos/farmacologia
Azadirachta/química
Limoninas/química
Limoninas/farmacologia
[Mh] Termos MeSH secundário: Animais
Antimaláricos/síntese química
Antimaláricos/isolamento & purificação
Antineoplásicos/síntese química
Antineoplásicos/isolamento & purificação
Linhagem Celular Tumoral
Proliferação Celular/efeitos dos fármacos
Seres Humanos
Limoninas/síntese química
Limoninas/isolamento & purificação
Malária/tratamento farmacológico
Malária Falciparum/tratamento farmacológico
Camundongos
Camundongos Endogâmicos BALB C
Neoplasias/tratamento farmacológico
Plasmodium berghei/efeitos dos fármacos
Plasmodium falciparum/efeitos dos fármacos
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antimalarials); 0 (Antineoplastic Agents); 0 (Limonins); 18385-59-6 (epoxyazadiradione)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170908
[Lr] Data última revisão:
170908
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170419
[St] Status:MEDLINE



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