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[PMID]:28511560
[Au] Autor:Li W; Xiao Y
[Ad] Endereço:a School of Chemical and Environmental Engineering , Hanshan Normal University , Chaozhou , P.R. China.
[Ti] Título:Synthesis and in vitro antitumour activities of lupeol derivatives.
[So] Source:Nat Prod Res;32(1):48-53, 2018 Jan.
[Is] ISSN:1478-6427
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Nine lupeol derivatives were synthesised and assayed in vitro for their antitumour activities against three human tumour cells lines, A549, LAC and HepG2. Of lupeol derivaties, six were new compounds, and five compounds against A549 cells, four compounds against HepG2 cells and three compounds against LAC cells were effective in reducing viability, and the most promising compounds 5, 6 and 9 exhibited high activities against lung and liver cancer cells, even higher activities than those of adriamycin.
[Mh] Termos MeSH primário: Antineoplásicos/química
Antineoplásicos/farmacologia
Triterpenos Pentacíclicos/química
[Mh] Termos MeSH secundário: Células A549
Antineoplásicos/síntese química
Linhagem Celular Tumoral
Técnicas de Química Sintética
Ensaios de Seleção de Medicamentos Antitumorais
Células Hep G2
Seres Humanos
Concentração Inibidora 50
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Pentacyclic Triterpenes); O268W13H3O (lupeol)
[Em] Mês de entrada:1803
[Cu] Atualização por classe:180301
[Lr] Data última revisão:
180301
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170518
[St] Status:MEDLINE
[do] DOI:10.1080/14786419.2017.1329729


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[PMID]:29196105
[Au] Autor:Lu Y; Kan H; Wang Y; Wang D; Wang X; Gao J; Zhu L
[Ad] Endereço:Institute of Nautical Medicine, Nantong University, Nantong 226019, China.
[Ti] Título:Asiatic acid ameliorates hepatic ischemia/reperfusion injury in rats via mitochondria-targeted protective mechanism.
[So] Source:Toxicol Appl Pharmacol;338:214-223, 2018 01 01.
[Is] ISSN:1096-0333
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:It has been proved that asiatic acid (AA) directly targets mitochondria and acts as a mild mitochondrial uncoupler. In this study, we aim to investigate the protective effects of AA against ischemia/reperfusion (I/R)-induced liver injury in rats and some underlying mechanisms involved were elucidated. The results showed that 50mg/kg AA pre-treatment significantly reduced I/R-induced liver damage, characterized by the decreased release of aspartate aminotransferase (AST) and TNF-α. Furthermore, AA pre-treatment dramatically inhibited the production of MDA and increased the hepatic SOD, catalase activities and GSH levels in liver tissue of I/R rats which indicated that AA ameliorated I/R-induced liver damage by reducing oxidative stress. In isolated liver mitochondria in I/R rats, AA improved mitochondrial respiration, decreased mitochondrial MDA level, prevented I/R-induced drop of mitochondrial membrane potential (MMP) and increased ATP content, indicating the protective effect of AA against I/R-induced mitochondrial oxidative damage. In isolated liver mitochondria from normal rats, AA was found to effectively block succinate-driven H O production no matter of the presence or absence of rotenone. In addition, AA showed a clear protective effect against anoxia/reoxygenation (A/R)-induced injury in isolated rat liver mitochondria when malate/glutamate were used as respiratory substrates. After AA treatment, mitochondrial respiratory dysfunction induced by A/R was ameliorated. Also, A/R-induced mitochondrial ROS generation was significantly inhibited by AA. In conclusion, AA can attenuate I/R-induced liver damage in rats and A/R-induced mitochondrial injury in isolated rat liver mitochondria by inhibiting oxidative stress and restoring mitochondrial function. Therefore, AA might have potential as a mitochondrial protective agent for use in clinical treatment of hepatic I/R injury.
[Mh] Termos MeSH primário: Fígado/irrigação sanguínea
Mitocôndrias Hepáticas/efeitos dos fármacos
Triterpenos Pentacíclicos/farmacologia
Traumatismo por Reperfusão/tratamento farmacológico
[Mh] Termos MeSH secundário: Animais
Masculino
Malondialdeído/análise
Triterpenos Pentacíclicos/uso terapêutico
Ratos
Ratos Sprague-Dawley
Espécies Reativas de Oxigênio/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Pentacyclic Triterpenes); 0 (Reactive Oxygen Species); 4Y8F71G49Q (Malondialdehyde); 9PA5A687X5 (asiatic acid)
[Em] Mês de entrada:1801
[Cu] Atualização por classe:180213
[Lr] Data última revisão:
180213
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:171203
[St] Status:MEDLINE


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[PMID]:28930532
[Au] Autor:Ahmad Rather M; Justin Thenmozhi A; Manivasagam T; Dhivya Bharathi M; Essa MM; Guillemin GJ
[Ad] Endereço:Department of Biochemistry and Biotechnology, Annamalai University, Annamalainagar, Tamil Nadu 608002, India.
[Ti] Título:Neuroprotective role of Asiatic acid in aluminium chloride induced rat model of Alzheimer's disease.
[So] Source:Front Biosci (Schol Ed);10:262-275, 2018 01 01.
[Is] ISSN:1945-0524
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Alzheimer's disease (AD) is the most common form of dementia, characterized by memory loss, cognitive impairment and personality disorders accompanied by diffuse structural abnormalities in the brain of elderly people. The current investigation explored the neuroprotective potential of asiatic acid (AA), a natural triterpene of on aluminium chloride (AlCl ) induced rat model of AD. Oral administration of AlCl (100 mg/kg b.w.) for 42 days significantly elevated the levels of Al, activity of acetyl cholinesterase and expressions of amyloid precursor protein, amyloid beta , beta and gamma secretases, glial fibrillary acidic protein, ionized calcium binding adaptor molecule 1, interleukins -1ß, 6, 4, 2, tumor necrosis factor alpha, inducible nitric oxide synthase, nuclear factor- k beta and cyclooxygenase-2 in the hippocampus and cortex  compared to the control group. Our observations suggested that AA treatment mitigated AlCl induced AD associated pathologies, which might be due to its multiple pharmacological actions. Further studies are necessary in order to explore the link between AlCl -mediated oxidative stress and associated apoptosis to establish its neuroprotective role in AD.
[Mh] Termos MeSH primário: Doença de Alzheimer/tratamento farmacológico
Fármacos Neuroprotetores/farmacologia
Triterpenos Pentacíclicos/farmacologia
[Mh] Termos MeSH secundário: Compostos de Alumínio
Doença de Alzheimer/induzido quimicamente
Doença de Alzheimer/metabolismo
Doença de Alzheimer/patologia
Amiloide/metabolismo
Secretases da Proteína Precursora do Amiloide/metabolismo
Peptídeos beta-Amiloides/metabolismo
Precursor de Proteína beta-Amiloide/metabolismo
Animais
Apoptose/efeitos dos fármacos
Cloretos
Modelos Animais de Doenças
Masculino
Estresse Oxidativo/efeitos dos fármacos
Distribuição Aleatória
Ratos
Ratos Wistar
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Aluminum Compounds); 0 (Amyloid); 0 (Amyloid beta-Peptides); 0 (Amyloid beta-Protein Precursor); 0 (Chlorides); 0 (Neuroprotective Agents); 0 (Pentacyclic Triterpenes); 3CYT62D3GA (aluminum chloride); 9PA5A687X5 (asiatic acid); EC 3.4.- (Amyloid Precursor Protein Secretases)
[Em] Mês de entrada:1712
[Cu] Atualização por classe:180213
[Lr] Data última revisão:
180213
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170921
[St] Status:MEDLINE


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[PMID]:29232409
[Au] Autor:Kangsamaksin T; Chaithongyot S; Wootthichairangsan C; Hanchaina R; Tangshewinsirikul C; Svasti J
[Ad] Endereço:Department of Biochemistry, Faculty of Science, Mahidol University, Bangkok, Thailand.
[Ti] Título:Lupeol and stigmasterol suppress tumor angiogenesis and inhibit cholangiocarcinoma growth in mice via downregulation of tumor necrosis factor-α.
[So] Source:PLoS One;12(12):e0189628, 2017.
[Is] ISSN:1932-6203
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Lupeol and stigmasterol, major phytosterols in various herbal plants, possess anti-inflammatory activities and have been proposed as candidates for anti-cancer agents, but their molecular mechanisms are still unclear. Here, we investigated the effects of lupeol and stigmasterol on tumor and endothelial cells in vitro and their anti-cancer activities in vivo. Our results demonstrated that lupeol and stigmasterol suppressed cell viability, migration, and morphogenesis of human umbilical vein endothelial cells (HUVECs) but not cholangiocarcinoma (CCA) cells. Expression analyses showed that the treatment of both compounds significantly reduced the transcript level of tumor necrosis factor-α (TNF-α), and Western blot analyses further revealed a decrease in downstream effector levels of VEGFR-2 signaling, including phosphorylated forms of Src, Akt, PCL, and FAK, which were rescued by TNF-α treatment. In vivo, lupeol and stigmasterol disrupted tumor angiogenesis and reduced the growth of CCA tumor xenografts. Immunohistochemical analyses confirmed a decrease in CD31-positive vessel content and macrophage recruitment upon treatment. These findings indicate that lupeol and stigmasterol effectively target tumor endothelial cells and suppress CCA tumor growth by their anti-inflammatory activities and are attractive candidates for anti-cancer treatment of CCA tumors.
[Mh] Termos MeSH primário: Proliferação Celular/efeitos dos fármacos
Colangiocarcinoma/patologia
Regulação para Baixo/efeitos dos fármacos
Neovascularização Patológica/prevenção & controle
Triterpenos Pentacíclicos/farmacologia
Estigmasterol/farmacologia
Fator de Necrose Tumoral alfa/metabolismo
[Mh] Termos MeSH secundário: Animais
Colangiocarcinoma/irrigação sanguínea
Células Endoteliais da Veia Umbilical Humana
Seres Humanos
Camundongos
Camundongos Endogâmicos C57BL
Transdução de Sinais
Fator A de Crescimento do Endotélio Vascular/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Pentacyclic Triterpenes); 0 (Tumor Necrosis Factor-alpha); 0 (Vascular Endothelial Growth Factor A); 99WUK5D0Y8 (Stigmasterol); O268W13H3O (lupeol)
[Em] Mês de entrada:1801
[Cu] Atualização por classe:180104
[Lr] Data última revisão:
180104
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:171213
[St] Status:MEDLINE
[do] DOI:10.1371/journal.pone.0189628


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[PMID]:28873615
[Au] Autor:Olmo-García L; Bajoub A; Monasterio RP; Fernández-Gutiérrez A; Carrasco-Pancorbo A
[Ad] Endereço:Department of Analytical Chemistry, Faculty of Sciences, University of Granada, Ave. Fuentenueva s/n, E-18071 Granada, Spain. Electronic address: luciaolmo@ugr.es.
[Ti] Título:Development and validation of LC-MS-based alternative methodologies to GC-MS for the simultaneous determination of triterpenic acids and dialcohols in virgin olive oil.
[So] Source:Food Chem;239:631-639, 2018 Jan 15.
[Is] ISSN:0308-8146
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Pentacyclic triterpenes are minor, but very relevant compounds found in virgin olive oil (VOO). A rapid and reliable LC-MS method for determining the triterpenic acids and dialcohols (after ultrasound assisted extraction) from VOO has been developed, giving an alternative to the widely used GC (FID/MS) methodologies. The analytical parameters of the proposed method were exhaustively checked, establishing limits of detection (from 1 to 95µg/l) and quantification, precision (RSD values for inter-day repeatability were found between 4.2 and 7.3% considering area values), trueness (within the range 92.7 and 100.5%) and evaluating possible matrix effect (which was no significant). The method was applied to the analysis of six triterpenic compounds in 11 monovarietal VOOs and the results compared with the quantitative GC-MS data. Moreover, the direct injection (after a simple dilution) of the samples into the LC-MS system was also tested, in an attempt to proffer an even simpler sample treatment.
[Mh] Termos MeSH primário: Azeite de Oliva
[Mh] Termos MeSH secundário: Cromatografia Líquida
Cromatografia Gasosa-Espectrometria de Massas
Espectrometria de Massas
Triterpenos Pentacíclicos
[Pt] Tipo de publicação:JOURNAL ARTICLE; VALIDATION STUDIES
[Nm] Nome de substância:
0 (Olive Oil); 0 (Pentacyclic Triterpenes)
[Em] Mês de entrada:1711
[Cu] Atualização por classe:171128
[Lr] Data última revisão:
171128
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170907
[St] Status:MEDLINE


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[PMID]:28791824
[Au] Autor:Wojnicz D; Tichaczek-Goska D; Korzekwa K; Kicia M; Hendrich A
[Ad] Endereço:Department of Biology and Medical Parasitology, Wroclaw Medical University, Poland.
[Ti] Título:Anti-enterococcal activities of pentacyclic triterpenes.
[So] Source:Adv Clin Exp Med;26(3):483-490, 2017 May-Jun.
[Is] ISSN:1899-5276
[Cp] País de publicação:Poland
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Asiatic (AA) and ursolic (UA) acids are widely studied phytochemicals, but their antimicrobial properties are still poorly understood. Therefore our research has focused on their activity against uropathogenic Enterococcus faecalis strains. OBJECTIVES: The aim of this research was to determine the influence of AA and UA on the growth, cell morphology, virulence factors and biofilm formation by E. faecalis strains. MATERIAL AND METHODS: AA and UA were purchased from Sigma-Aldrich. E. faecalis strains were isolated from the urine samples of patients with urinary tract infections. The strains were checked for the presence of virulence genes using the PCR method. Their antimicrobial susceptibility was performed using the disc diffusion method. The MICs of triterpenes were determined using the broth microdilution method. The hydrophobicity of cells was established by salt aggregation test. Lipase and lecithinase activities were determined by using an agar medium containing egg yolk emulsion. DNase agar was used for the detection of DNase synthesis. Hemolytic activity was established using a sheep-blood agar. Todd-Hewitt agar medium containing gelatin was used for determination of gelatinase activity. The anti-biofilm activity of asiatic acid and ursolic acid was tested on polystyrene microtiter plates. It was examined using time-kill and biofilm assays. RESULTS: Reduction of growth and enzyme synthesis after exposure of E. faecalis to the acids was observed. None of the acids changed the hydrophobicity of bacteria. Stronger anti-biofilm activity was observed when the bacteria were incubated with AA. Thus, reduction of both the survival and the virulence factors will make bacteria less infectious. CONCLUSIONS: Based on the results obtained, we can assume that the triterpenes investigated should be considered natural components of a human diet rather than as antibacterial agents used on their own.
[Mh] Termos MeSH primário: Antibacterianos/farmacologia
Enterococcus faecalis/efeitos dos fármacos
Triterpenos Pentacíclicos/farmacologia
[Mh] Termos MeSH secundário: Biofilmes/efeitos dos fármacos
Infecções por Bactérias Gram-Positivas/tratamento farmacológico
Infecções por Bactérias Gram-Positivas/metabolismo
Seres Humanos
Lipase/metabolismo
Testes de Sensibilidade Microbiana/métodos
Fosfolipases/metabolismo
Triterpenos/farmacologia
Virulência/efeitos dos fármacos
Fatores de Virulência/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anti-Bacterial Agents); 0 (Pentacyclic Triterpenes); 0 (Triterpenes); 0 (Virulence Factors); 9PA5A687X5 (asiatic acid); EC 3.1.- (Phospholipases); EC 3.1.1.3 (Lipase); P3M2575F3F (ursolic acid)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171004
[Lr] Data última revisão:
171004
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170810
[St] Status:MEDLINE
[do] DOI:10.17219/acem/62245


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[PMID]:28739601
[Au] Autor:Fialho MFP; Brusco I; da Silva Brum E; Piana M; Boligon AA; Trevisan G; Oliveira SM
[Ad] Endereço:Neurotoxicity and Psychopharmacology Laboratory, Center of Natural and Exact Sciences, Federal University of Santa Maria, Santa Maria, RS, Brazil.
[Ti] Título: Lam. crude extract presents antinociceptive effect on an arthritic pain model in mice.
[So] Source:Biochem J;474(17):2993-3010, 2017 Aug 17.
[Is] ISSN:1470-8728
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Arthritis is a chronic inflammatory disease which reduces the life quality of affected individuals. Therapeutic tools used for treating inflammatory pain are associated with several undesirable effects. Lam., known as 'Barbasco' or 'Cambara', is mostly used in several disorders and possesses antirheumatic, anti-inflammatory, and analgesic properties. Here, we investigated the antinociceptive and anti-inflammatory effects of the crude extract applied orally and topically in acute pain models and an arthritic pain model induced by complete Freund's adjuvant (CFA) paw injection in male mice (25-30 g). The high-performance liquid chromatography (HPLC) of the extract crude revealed the presence of the lupeol, stigmasterol, and ß-sitosterol. The stability study of the gel did not show relevant changes at low temperatures. The oral treatment with the extract prevented the capsaicin-induced spontaneous nociception and the acetic acid-induced abdominal writhing, but did not alter the thermal threshold in the tail immersion test. The antinociceptive effect was not reversed by naloxone in the capsaicin test. The oral or topical treatment reversed the CFA-induced mechanical allodynia and thermal hyperalgesia with maximum inhibition ( ) of 69 ± 6 and 68 ± 5% as well as 78 ± 15 and 87 ± 12%, respectively. Moreover, the topical but not oral treatment inhibited the CFA-induced cell infiltration, but did not reduce the paw edema significantly. The oral treatment with did not cause adverse effects. These findings suggest that the oral or topical treatment with presents antinociceptive actions in an arthritic pain model without causing adverse effects.
[Mh] Termos MeSH primário: Analgésicos não Entorpecentes/uso terapêutico
Anti-Inflamatórios não Esteroides/uso terapêutico
Artrite Experimental/tratamento farmacológico
Buddleja/química
Extratos Vegetais/uso terapêutico
Folhas de Planta/química
[Mh] Termos MeSH secundário: Dor Aguda/tratamento farmacológico
Administração Cutânea
Administração Oral
Analgésicos não Entorpecentes/administração & dosagem
Analgésicos não Entorpecentes/efeitos adversos
Analgésicos não Entorpecentes/química
Animais
Anti-Inflamatórios não Esteroides/administração & dosagem
Anti-Inflamatórios não Esteroides/efeitos adversos
Anti-Inflamatórios não Esteroides/química
Brasil
Buddleja/crescimento & desenvolvimento
Estabilidade de Medicamentos
Armazenamento de Medicamentos
Etnofarmacologia
Géis
Temperatura Alta/efeitos adversos
Masculino
Camundongos
Triterpenos Pentacíclicos/administração & dosagem
Triterpenos Pentacíclicos/efeitos adversos
Triterpenos Pentacíclicos/análise
Triterpenos Pentacíclicos/uso terapêutico
Extratos Vegetais/administração & dosagem
Extratos Vegetais/efeitos adversos
Extratos Vegetais/química
Folhas de Planta/crescimento & desenvolvimento
Sitosteroides/administração & dosagem
Sitosteroides/efeitos adversos
Sitosteroides/análise
Sitosteroides/uso terapêutico
Estigmasterol/administração & dosagem
Estigmasterol/efeitos adversos
Estigmasterol/análise
Estigmasterol/uso terapêutico
Viscosidade
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Analgesics, Non-Narcotic); 0 (Anti-Inflammatory Agents, Non-Steroidal); 0 (Gels); 0 (Pentacyclic Triterpenes); 0 (Plant Extracts); 0 (Sitosterols); 5LI01C78DD (gamma-sitosterol); 99WUK5D0Y8 (Stigmasterol); O268W13H3O (lupeol)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170828
[Lr] Data última revisão:
170828
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170726
[St] Status:MEDLINE
[do] DOI:10.1042/BCJ20170008


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[PMID]:28700628
[Au] Autor:Chaisawang P; Sirichoat A; Chaijaroonkhanarak W; Pannangrong W; Sripanidkulchai B; Wigmore P; Welbat JU
[Ad] Endereço:Department of Anatomy, Faculty of Medicine, Khon Kaen University, Khon Kaen, Thailand.
[Ti] Título:Asiatic acid protects against cognitive deficits and reductions in cell proliferation and survival in the rat hippocampus caused by 5-fluorouracil chemotherapy.
[So] Source:PLoS One;12(7):e0180650, 2017.
[Is] ISSN:1932-6203
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The chemotherapy drug, 5-fluorouracil (5-FU), has been reported to cause cognitive impairments in cancer patients. The drug also reduces cell proliferation and survival in the brain. Asiatic acid (AA) is a triterpene compound found in Centella asiatica that can protect against reduction of neurogenesis in the hippocampus and memory deficits induced by valproic acid (VPA). In the present study, we investigated the preventive effects of AA on the deficits in spatial working memory and cell proliferation and survival caused by 5-FU chemotherapy in a rat model. Male Sprague Dawley rats received 5-FU (5 i.v. injections, 25 mg/kg) on day 8, 11, 14, 17 and 20 of the study. This was co-administered with AA (30 mg/kg, oral gavage tube) either 20 days before receiving 5-FU (preventive), after receiving 5-FU (recovery), or for the entire period of the experiment (throughout). Spatial working memory was determined using the novel object location (NOL) test and hippocampal cell proliferation and survival of dividing cells were quantified using immunohistochemistry. Rats in the 5-FU alone and recovery groups showed memory deficits in the NOL test and reductions in cell proliferation and cell survival in the subgranular zone (SGZ) of the hippocampal dentate gyrus. Rats in the control, AA alone, and both preventive and throughout co-administration groups, however, did not exhibit these characteristics. The results showed that 5-FU chemotherapy impaired memory and reduced cell proliferation and cell survival in the SGZ of the hippocampal dentate gyrus. However, these impairments in the animals receiving 5-FU chemotherapy were restored to control levels when AA was co-administered before and during 5-FU treatment. These data demonstrate that AA can prevent the spatial working memory and hippocampal neurogenesis impairments caused by 5-FU chemotherapy.
[Mh] Termos MeSH primário: Transtornos Cognitivos/patologia
Transtornos Cognitivos/prevenção & controle
Fluoruracila/efeitos adversos
Hipocampo/patologia
Fármacos Neuroprotetores/uso terapêutico
Triterpenos Pentacíclicos/uso terapêutico
[Mh] Termos MeSH secundário: Animais
Contagem de Células
Proliferação Celular/efeitos dos fármacos
Sobrevivência Celular/efeitos dos fármacos
Giro Denteado/efeitos dos fármacos
Giro Denteado/patologia
Comportamento Exploratório
Hipocampo/efeitos dos fármacos
Masculino
Fármacos Neuroprotetores/farmacologia
Triterpenos Pentacíclicos/farmacologia
Ratos Sprague-Dawley
Memória Espacial/efeitos dos fármacos
Fatores de Tempo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Neuroprotective Agents); 0 (Pentacyclic Triterpenes); 9PA5A687X5 (asiatic acid); U3P01618RT (Fluorouracil)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170925
[Lr] Data última revisão:
170925
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170713
[St] Status:MEDLINE
[do] DOI:10.1371/journal.pone.0180650


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[PMID]:28654752
[Au] Autor:Ruiz-Rodríguez MA; Vedani A; Flores-Mireles AL; Cháirez-Ramírez MH; Gallegos-Infante JA; González-Laredo RF
[Ad] Endereço:Department of Chemical and Biochemical Engineering, Tecnológico Nacional de México-Instituto Tecnológico de Durango , Boulevard Felipe Pescador 1830 Ote., 34080 Durango, México.
[Ti] Título:In Silico Prediction of the Toxic Potential of Lupeol.
[So] Source:Chem Res Toxicol;30(8):1562-1571, 2017 Aug 21.
[Is] ISSN:1520-5010
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Lupeol is a natural triterpenoid found in many plant species such as mango. This compound is the principal active component of many traditional herbal medicines. In the past decade, a considerable number of publications dealt with lupeol and its analogues due to the interest in their pharmacological activities against cancer, inflammation, arthritis, diabetes, and heart disease. To identify further potential applications of lupeol and its analogues, it is necessary to investigate their mechanisms of action, particularly their interaction with off-target proteins that may trigger adverse effects or toxicity. In this study, we simulated and quantified the interaction of lupeol and 11 of its analogues toward a series of 16 proteins known or suspected to trigger adverse effects employing the VirtualToxLab. This software provides a thermodynamic estimate of the binding affinity, and the results were challenged by molecular-dynamics simulations, which allow probing the kinetic stability of the underlying protein-ligand complexes. Our results indicate that there is a moderate toxic potential for lupeol and some of its analogues, by targeting and binding to nuclear receptors involved in fertility, which could trigger undesired adverse effects.
[Mh] Termos MeSH primário: Triterpenos Pentacíclicos/química
Triterpenos Pentacíclicos/toxicidade
[Mh] Termos MeSH secundário: Animais
Células CACO-2
Permeabilidade da Membrana Celular/efeitos dos fármacos
Sobrevivência Celular/efeitos dos fármacos
Cães
Seres Humanos
Ligações de Hidrogênio
Células Madin Darby de Rim Canino
Mangifera/química
Mangifera/metabolismo
Camundongos
Simulação de Dinâmica Molecular
Triterpenos Pentacíclicos/metabolismo
Ligação Proteica
Estrutura Terciária de Proteína
Proteínas/química
Proteínas/metabolismo
Relação Quantitativa Estrutura-Atividade
Ratos
Receptores Androgênicos/química
Receptores Androgênicos/metabolismo
Receptores Estrogênicos/química
Receptores Estrogênicos/metabolismo
Software
Termodinâmica
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Pentacyclic Triterpenes); 0 (Proteins); 0 (Receptors, Androgen); 0 (Receptors, Estrogen); O268W13H3O (lupeol)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170929
[Lr] Data última revisão:
170929
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170628
[St] Status:MEDLINE
[do] DOI:10.1021/acs.chemrestox.7b00070


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[PMID]:28568378
[Au] Autor:Tahsin T; Wansi JD; Al-Groshi A; Evans A; Nahar L; Martin C; Sarker SD
[Ad] Endereço:Medicinal Chemistry and Natural Products Research Group, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool, L3 3AF, UK.
[Ti] Título:Cytotoxic Properties of the Stem Bark of Citrus reticulata Blanco (Rutaceae).
[So] Source:Phytother Res;31(8):1215-1219, 2017 Aug.
[Is] ISSN:1099-1573
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The bioassay-guided fractionation of the n-hexane extract of Citrus reticulata Blanco (Rutaceae) stem bark yielded scoparone (1), xanthyletin (2), lupeol (3), ß-amyrin (4), stigmasterol (5), ß-sitosterol (6) and palmitic acid. The structures of these compounds were determined by comprehensive spectroscopic analyses, i.e., 1D and 2D NMR and EI-MS, and by comparison with the reported data. Extracts, fractions and isolated compounds 1-6 were assessed for cytotoxicity by the 3-(4,5-dimethylthiazol-2-yl)-2,5-dphenyltetrazolium bromide (MTT) assay against three human cancer cell lines, i.e., human lung adenocarcinoma cell line A549, human breast adenocarcinoma cell line MCF7 and human Caucasian prostate adenocarcinoma cell line PC3. Significant activity of the n-hexane and the dichloromethane extracts was observed against the breast cancer cell line MCF7 with IC s of 45.6 and 54.7 µg/mL, respectively. Moreover, the 70% ethyl acetate in n-hexane chromatographic fraction showed significant activity displaying IC values of 53.0, 52.4 and 49.1 µg/mL against the cancer cell lines A549, MCF7 and PC3, respectively. Encouragingly, an IC of 510.0 µg/mL against the human normal prostate cell line PNT2 indicated very low toxicity and hence favourable selectivity indices for the 70% ethyl acetate in n-hexane fraction in the range of 9.6-10.4 towards cell lines A549, MCF7 and PC3. Because compounds isolated from the above fraction only delivered IC values in the range of 18.2-96.3, 9.2-34.1 and 7.5-97.2 µg/mL against A549, MCF7 and PC3 cell lines, respectively, synergistic action between compounds is suggested. Bioassay results valorize the anticancer effectivity of the stem bark of this plant in Cameroonian pharmacopoeia. Copyright © 2017 John Wiley & Sons, Ltd.
[Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/farmacologia
Citrus/química
Casca de Planta/química
Extratos Vegetais/farmacologia
[Mh] Termos MeSH secundário: Antineoplásicos Fitogênicos/química
Linhagem Celular Tumoral
Fracionamento Químico
Cumarínicos
Seres Humanos
Ácido Oleanólico/análogos & derivados
Ácido Palmítico
Triterpenos Pentacíclicos
Extratos Vegetais/química
Sitosteroides
Estigmasterol
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents, Phytogenic); 0 (Coumarins); 0 (Pentacyclic Triterpenes); 0 (Plant Extracts); 0 (Sitosterols); 2V16EO95H1 (Palmitic Acid); 3N789LD38N (xanthyletine); 5LI01C78DD (gamma-sitosterol); 6SMK8R7TGJ (Oleanolic Acid); 99WUK5D0Y8 (Stigmasterol); H5841PDT4Y (scoparone); KM8353IPSO (amyrin); O268W13H3O (lupeol)
[Em] Mês de entrada:1710
[Cu] Atualização por classe:171003
[Lr] Data última revisão:
171003
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170602
[St] Status:MEDLINE
[do] DOI:10.1002/ptr.5842



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