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[PMID]:28143677
[Au] Autor:Rossington SB; Hadfield JA; Shnyder SD; Wallace TW; Williams KJ
[Ad] Endereço:School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
[Ti] Título:Tubulin-binding dibenz[c,e]oxepines: Part 2. Structural variation and biological evaluation as tumour vasculature disrupting agents.
[So] Source:Bioorg Med Chem;25(5):1630-1642, 2017 Mar 01.
[Is] ISSN:1464-3391
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:5,7-Dihydro-3,9,10,11-tetramethoxybenz[c,e]oxepin-4-ol 1, prepared from a dibenzyl ether precursor via Pd-catalysed intramolecular direct arylation, possesses broad-spectrum in vitro cytotoxicity towards various tumour cell lines, and induces vascular shutdown, necrosis and growth delay in tumour xenografts in mice at sub-toxic doses. The biological properties of 1 and related compounds can be attributed to their ability to inhibit microtubule assembly at the micromolar level, by binding reversibly to the same site of the tubulin αß-heterodimer as colchicine 2 and the allocolchinol, N-acetylcolchinol 4.
[Mh] Termos MeSH primário: Dibenzoxepinas/metabolismo
Neoplasias/irrigação sanguínea
Tubulina (Proteína)/metabolismo
[Mh] Termos MeSH secundário: Animais
Linhagem Celular Tumoral
Dibenzoxepinas/química
Dibenzoxepinas/farmacologia
Relação Dose-Resposta a Droga
Xenoenxertos
Seres Humanos
Camundongos
Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Dibenzoxepins); 0 (Tubulin)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170808
[Lr] Data última revisão:
170808
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170202
[St] Status:MEDLINE


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[PMID]:28012710
[Au] Autor:Cardile V; Graziano AC; Avola R; Piovano M; Russo A
[Ad] Endereço:Department of Biomedical and Biotechnological Sciences, Section of Physiology, University of Catania, V.le A. Doria 6, 95125, Catania, Italy.
[Ti] Título:Potential anticancer activity of lichen secondary metabolite physodic acid.
[So] Source:Chem Biol Interact;263:36-45, 2017 Feb 01.
[Is] ISSN:1872-7786
[Cp] País de publicação:Ireland
[La] Idioma:eng
[Ab] Resumo:Secondary metabolites present in lichens, which comprise aliphatic, cycloaliphatic, aromatic and terpenic compounds, are unique with respect to those of higher plants and show interesting biological and pharmacological activities. However, only a few of these compounds, have been assessed for their effectiveness against various in vitro cancer models. In the present study, we investigated the cytotoxicity of three lichen secondary metabolites (atranorin, gyrophoric acid and physodic acid) on A375 melanoma cancer cell line. The tested compounds arise from different lichen species collected in different areas of Continental and Antarctic Chile. The obtained results confirm the major efficiency of depsidones. In fact, depsides atranorin and gyrophoric acid, showed a lower activity inhibiting the melanoma cancer cells only at more high concentrations. Whereas the depsidone physodic acid, showed a dose-response relationship in the range of 6.25-50 µM concentrations in A375 cells, activating an apoptotic process, that probably involves the reduction of Hsp70 expression. Although the molecular mechanism, by which apoptosis is induced by physodic acid remains unclear, and of course further studies are needed, the results here reported confirm the promising biological properties of depsidone compounds, and may offer a further impulse to the development of analogues with more powerful efficiency against melanoma cells.
[Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/toxicidade
Apoptose/efeitos dos fármacos
Dibenzoxepinas/toxicidade
Líquens/metabolismo
[Mh] Termos MeSH secundário: Antineoplásicos Fitogênicos/química
Benzoatos/química
Benzoatos/toxicidade
Western Blotting
Caspase 3/metabolismo
Linhagem Celular Tumoral
Proliferação Celular/efeitos dos fármacos
Dibenzoxepinas/química
Regulação para Baixo/efeitos dos fármacos
Proteínas de Choque Térmico HSP70/metabolismo
Seres Humanos
Hidroxibenzoatos/química
Hidroxibenzoatos/toxicidade
Proteínas Proto-Oncogênicas c-bcl-2/metabolismo
Espécies Reativas de Oxigênio/metabolismo
Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz
Espectrofotometria Infravermelho
Proteína X Associada a bcl-2/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents, Phytogenic); 0 (Benzoates); 0 (Dibenzoxepins); 0 (HSP70 Heat-Shock Proteins); 0 (Hydroxybenzoates); 0 (Proto-Oncogene Proteins c-bcl-2); 0 (Reactive Oxygen Species); 0 (bcl-2-Associated X Protein); 450U2VJ2VG (atranorin); BAQ44A6C6H (gyrophoric acid); EC 3.4.22.- (Caspase 3); X901BNT6BF (physodic acid)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:161226
[St] Status:MEDLINE


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[PMID]:27206701
[Au] Autor:Emsen B; Turkez H; Togar B; Aslan A
[Ad] Endereço:1 Department of Biology, Kamil Özdag Faculty of Science, Karamanoglu Mehmetbey University, Karaman, Turkey.
[Ti] Título:Evaluation of antioxidant and cytotoxic effects of olivetoric and physodic acid in cultured human amnion fibroblasts.
[So] Source:Hum Exp Toxicol;36(4):376-385, 2017 Apr.
[Is] ISSN:1477-0903
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:It is known that lichens are utilized for the treatment of many diseases including ulcer, diabetes, and cancer for many years. Secondary metabolites in the structure of the lichens provide various activity properties for them. In the present study, cytotoxic and oxidative effects of main constituents of Pseudevernia furfuracea (L.) Zopf (Parmeliaceae), olivetoric acid (OA), and physodic acid (PA) were investigated on cultured human amnion fibroblasts (HAFs). OA and PA were isolated from P. furfuracea using column chromatography and their structures were determined by proton nuclear magnetic resonance and carbon-13 nuclear magnetic resonance. HAFs were incubated during 48 h in the presence of OA and PA, at different concentrations from 6.25 mg/L to 200 mg/L. OA showed higher cytotoxicity than PA. In fact, median inhibitory concentration values of OA and PA were 571.27 and 3373.69 mg/L, respectively. The lower concentrations (<50 mg/L) of OA and PA did not cause oxidative stress and genotoxicity; furthermore, they supported anti-oxidative capacity of HAFs. Therefore, all these data suggested that both tested metabolites, especially PA might be developed as natural health medicine to protect human body against oxidative stress and genotoxicity. As far as we know, this is the first report on the cytotoxic and anti-oxidative activities of OA and PA on HAFs.
[Mh] Termos MeSH primário: Antioxidantes/farmacologia
Dibenzoxepinas/farmacologia
Fibroblastos/efeitos dos fármacos
Salicilatos/farmacologia
[Mh] Termos MeSH secundário: Âmnio/citologia
Sobrevivência Celular/efeitos dos fármacos
Células Cultivadas
Dano ao DNA
Desoxiadenosinas/metabolismo
Fibroblastos/metabolismo
Seres Humanos
Líquens/química
Estresse Oxidativo/efeitos dos fármacos
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (8-hydroxy-2'-deoxyadenosine); 0 (Antioxidants); 0 (Deoxyadenosines); 0 (Dibenzoxepins); 0 (Salicylates); 0 (olivetoric acid); X901BNT6BF (physodic acid)
[Em] Mês de entrada:1708
[Cu] Atualização por classe:170803
[Lr] Data última revisão:
170803
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160522
[St] Status:MEDLINE
[do] DOI:10.1177/0960327116650012


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[PMID]:27765373
[Au] Autor:Reddy RG; Veeraval L; Maitra S; Chollet-Krugler M; Tomasi S; Dévéhat FL; Boustie J; Chakravarty S
[Ad] Endereço:Chemical Biology, CSIR- Indian Institute of Chemical Technology, Tarnaka, Uppal Road, Hyderabad 500007, India.
[Ti] Título:Lichen-derived compounds show potential for central nervous system therapeutics.
[So] Source:Phytomedicine;23(12):1527-1534, 2016 Nov 15.
[Is] ISSN:1618-095X
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Natural products from lichens are widely investigated for their biological properties, yet their potential as central nervous system (CNS) therapeutic agents is less explored. PURPOSE: The present study investigated the neuroactive properties of selected lichen compounds (atranorin, perlatolic acid, physodic acid and usnic acid), for their neurotrophic, neurogenic and acetylcholine esterase (AChE) activities. METHODS: Neurotrophic activity (neurite outgrowth) was determined using murine neuroblastoma Neuro2A cells. A MTT assay was performed to assess the cytotoxicity of compounds at optimum neurotrophic activity. Neuro2A cells treated with neurotrophic lichen compounds were used for RT-PCR to evaluate the induction of genes that code for the neurotrophic markers BDNF and NGF. Immunoblotting was used to assess acetyl H3 and H4 levels, the epigenetic markers associated with neurotrophic and/or neurogenic activity. The neurogenic property of the compounds was determined using murine hippocampal primary cultures. AChE inhibition activity was performed using a modified Ellman's esterase method. RESULTS: Lichen compounds atranorin, perlatolic acid, physodic acid and (+)-usnic acid showed neurotrophic activity in a preliminary cell-based screening based on Neuro2A neurite outgrowth. Except for usnic acid, no cytotoxic effects were observed for the two depsides (atranorin and perlatolic acid) and the alkyl depsidone (physodic acid). Perlatolic acid appears to be promising, as it also exhibited AChE inhibition activity and potent proneurogenic activity. The neurotrophic lichen compounds (atranorin, perlatolic acid, physodic acid) modulated the gene expression of BDNF and NGF. In addition, perlatolic acid showed increased protein levels of acetyl H3 and H4 in Neuro2A cells. CONCLUSION: These lichen depsides and depsidones showed neuroactive properties in vitro (Neuro2A cells) and ex vivo (primary neural stem or progenitor cells), suggesting their potential to treat CNS disorders.
[Mh] Termos MeSH primário: Benzoatos/farmacologia
Benzofuranos/farmacologia
Sistema Nervoso Central/efeitos dos fármacos
Depsídeos/farmacologia
Dibenzoxepinas/farmacologia
Hidroxibenzoatos/farmacologia
Lactonas/farmacologia
Líquens/química
[Mh] Termos MeSH secundário: Acetilcolinesterase/metabolismo
Animais
Benzoatos/uso terapêutico
Benzofuranos/uso terapêutico
Produtos Biológicos/farmacologia
Produtos Biológicos/uso terapêutico
Fator Neurotrófico Derivado do Encéfalo/genética
Fator Neurotrófico Derivado do Encéfalo/metabolismo
Linhagem Celular
Sistema Nervoso Central/metabolismo
Doenças do Sistema Nervoso Central/tratamento farmacológico
Doenças do Sistema Nervoso Central/metabolismo
Inibidores da Colinesterase/farmacologia
Depsídeos/uso terapêutico
Dibenzoxepinas/uso terapêutico
Expressão Gênica
Hidroxibenzoatos/uso terapêutico
Lactonas/uso terapêutico
Camundongos
Fator de Crescimento Neural/genética
Fator de Crescimento Neural/metabolismo
Células-Tronco Neurais
Neurogênese/efeitos dos fármacos
Neurogênese/genética
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Benzoates); 0 (Benzofurans); 0 (Biological Products); 0 (Brain-Derived Neurotrophic Factor); 0 (Cholinesterase Inhibitors); 0 (Depsides); 0 (Dibenzoxepins); 0 (Hydroxybenzoates); 0 (Lactones); 0 (perlatolic acid); 0W584PFJ77 (usnic acid); 3580-77-6 (depsidone); 450U2VJ2VG (atranorin); 9061-61-4 (Nerve Growth Factor); EC 3.1.1.7 (Acetylcholinesterase); X901BNT6BF (physodic acid)
[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:161022
[St] Status:MEDLINE


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[PMID]:27300079
[Au] Autor:Talapatra SK; Rath O; Clayton E; Tomasi S; Kozielski F
[Ad] Endereço:Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy, University College London , 29-39 Brunswick Square, London WC1N 1AX, U.K.
[Ti] Título:Depsidones from Lichens as Natural Product Inhibitors of M-Phase Phosphoprotein 1, a Human Kinesin Required for Cytokinesis.
[So] Source:J Nat Prod;79(6):1576-85, 2016 Jun 24.
[Is] ISSN:1520-6025
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:M-Phase Phosphoprotein 1 (MPP1), a microtubule plus end directed kinesin, is required for the completion of cytokinesis. Previous studies have shown that MPP1 is upregulated in various types of bladder cancer. This article describes inhibitor screening leading to the identification of a new class of natural product inhibitors of MPP1. Two compounds with structural similarity, norlobaridone (1) and physodic acid (2), were found to inhibit MPP1. Physodic acid is not competitive with ATP, indicating the presence of an allosteric inhibitor-binding pocket. Initial drug-like property screening indicates that physodic acid is more soluble than norlobaridone and has more favorable lipophilicity. However, both suffer from high clearance in human microsomal stability assays mediated by the lability of the lactone ring as well as hydroxylation of the alkyl chains as shown by metabolite identification studies. In cell-based assays physodic acid is a weak inhibitor with EC50 values of about 30 µM in a range of tumor cell lines. The two depsidones identified and characterized here could be used for future improvement of their activity against MPP1 and will be useful chemical probes for studying this unique molecular motor in more depth.
[Mh] Termos MeSH primário: Depsídeos/isolamento & purificação
Dibenzoxepinas/isolamento & purificação
Cinesina/antagonistas & inibidores
Lactonas/isolamento & purificação
Líquens/química
[Mh] Termos MeSH secundário: Algoritmos
Protocolos de Quimioterapia Combinada Antineoplásica
Citocinese/efeitos dos fármacos
Depsídeos/química
Depsídeos/farmacologia
Dibenzoxepinas/química
Dibenzoxepinas/farmacologia
Seres Humanos
Cinesina/efeitos dos fármacos
Cinesina/metabolismo
Lactonas/química
Lactonas/farmacologia
Melfalan
Microtúbulos/efeitos dos fármacos
Microtúbulos/metabolismo
Estrutura Molecular
Prednisona
Procarbazina
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Depsides); 0 (Dibenzoxepins); 0 (Lactones); 0 (norlobaridone); 3580-77-6 (depsidone); 35S93Y190K (Procarbazine); EC 3.6.1.- (KIF20B protein, human); EC 3.6.4.4 (Kinesin); Q41OR9510P (Melphalan); VB0R961HZT (Prednisone); X901BNT6BF (physodic acid)
[Em] Mês de entrada:1705
[Cu] Atualização por classe:170517
[Lr] Data última revisão:
170517
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160615
[St] Status:MEDLINE
[do] DOI:10.1021/acs.jnatprod.5b00962


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[PMID]:27049956
[Au] Autor:Studzinska-Sroka E; Piotrowska H; Kucinska M; Murias M; Bylka W
[Ad] Endereço:a Department of Pharmacognosy , Poznan University of Medical Sciences , Poznan , Poland.
[Ti] Título:Cytotoxic activity of physodic acid and acetone extract from Hypogymnia physodes against breast cancer cell lines.
[So] Source:Pharm Biol;54(11):2480-2485, 2016 Nov.
[Is] ISSN:1744-5116
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:CONTEXT: Lichens produce specific secondary metabolites with different biological activity. OBJECTIVE: This study investigated the cytotoxic effects of physodic acid, in addition to the total phenolic content and cytotoxic and antioxidant activity of acetone extract from Hypogymnia physodes (L.) Nyl. (Parmeliaceae). MATERIALS AND METHODS: Cytotoxicity of physodic acid (0.1-100 µM) was assessed in MDA-MB-231, MCF-7 and T-47D breast cancer cell lines and a nontumorigenic MCF-10A cell line using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, neutral red uptake and crystal violet assays during 72 h of incubation. An MTT assay was also used to assess the cytotoxic effects of the acetone extract (0.1-100 µg/mL) in the MDA-MB-231, MCF-7, T-47D breast cancer cell lines after 72 h. The total phenolic content of the acetone extract, expressed as the gallic acid equivalent, was investigated using Folin-Ciocalteu reagent. The antioxidant activity of the extract was assessed by 2,2-diphenyl-1-picrylhydrazyl and ferric-reducing antioxidant power assays. RESULTS: The cytotoxic activity of physodic acid appeared to be strong in the tumorigenic cell lines (IC 46.0-93.9 µM). The compound was inactive against the nontumorigenic MCF-10A cell line (IC >100 µM). The acetone extract showed cytotoxicity in the breast cancer cell lines (IC 46.2-110.4 µg/mL). The acetone extract was characterized by a high content of polyphenols, and it had significant antioxidant activity. DISCUSSION AND CONCLUSION: Physodic acid and acetone extract from H. physodes displayed cytotoxic effects in the breast cancer cell lines. Furthermore, acetone extract from H. physodes possessed significant antioxidant properties.
[Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/farmacologia
Neoplasias da Mama/tratamento farmacológico
Dibenzoxepinas/farmacologia
Parmeliaceae
Extratos Vegetais/farmacologia
[Mh] Termos MeSH secundário: Antioxidantes/farmacologia
Neoplasias da Mama/patologia
Linhagem Celular Tumoral
Feminino
Seres Humanos
Parmeliaceae/química
Fenóis/análise
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents, Phytogenic); 0 (Antioxidants); 0 (Dibenzoxepins); 0 (Phenols); 0 (Plant Extracts); X901BNT6BF (physodic acid)
[Em] Mês de entrada:1703
[Cu] Atualização por classe:170303
[Lr] Data última revisão:
170303
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160407
[St] Status:MEDLINE


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[PMID]:26704132
[Au] Autor:Emsen B; Aslan A; Togar B; Turkez H
[Ad] Endereço:a Department of Biology, Kamil Özdag Faculty of Science , Karamanoglu Mehmetbey University , Karaman , Turkey ;
[Ti] Título:In vitro antitumor activities of the lichen compounds olivetoric, physodic and psoromic acid in rat neuron and glioblastoma cells.
[So] Source:Pharm Biol;54(9):1748-62, 2016 Sep.
[Is] ISSN:1744-5116
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Context Since methods utilised in the treatment of glioblastoma multiforme (GBM) are inadequate and have too many side effects, usage of herbal products in the treatment process comes into prominence. Lichens are symbiotic organisms used for medicinal purposes for many years. There are various anticancer treatments about components of two lichen species used in the present study. Objective Antitumor potential of three lichen secondary metabolites including olivetoric acid (OLA) and physodic acid (PHA) isolated from Pseudevernia furfuracea (L.) Zopf (Parmeliaceae) and psoromic acid (PSA) isolated from Rhizoplaca melanophthalma (DC.) Leuckert (Lecanoraceae) were investigated on human U87MG-GBM cell lines and primary rat cerebral cortex (PRCC) cells for the first time. Materials and methods PRCC cells used as healthy brain cells were obtained from Sprague-Dawley rats. The treatments were carried out on the cells cultured for 48 h. Cytotoxic effects of different concentrations (2.5, 5, 10, 20 and 40 mg/L) of metabolites on the cells were determined via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) analyses. Total antioxidant capacity (TAC) and total oxidant status (TOS) parameters were used for assessing oxidative alterations. Oxidative DNA damage potentials of metabolites were investigated via evaluating 8-hydroxy-2'-deoxyguanosine (8-OH-dG) levels. Results Median inhibitory concentration (IC50) values of OLA, PHA and PSA were 125.71, 698.19 and 79.40 mg/L for PRCC cells and 17.55, 410.72 and 56.22 mg/L for U87MG cells, respectively. It was revealed that cytotoxic effects of these metabolites showed positive correlation with concentration, LDH activity and oxidative DNA damage. Discussion and conclusion The present findings obtained in this study revealed that primarily OLA and then PSA had high potential for use in the treatment of GBM.
[Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/farmacologia
Benzoxepinas/farmacologia
Neoplasias Encefálicas/tratamento farmacológico
Ácidos Carboxílicos/farmacologia
Córtex Cerebral/efeitos dos fármacos
Dibenzoxepinas/farmacologia
Glioblastoma/tratamento farmacológico
Líquens
Neurônios/efeitos dos fármacos
Extratos Vegetais/farmacologia
Salicilatos/farmacologia
[Mh] Termos MeSH secundário: Animais
Antineoplásicos Fitogênicos/isolamento & purificação
Antineoplásicos Fitogênicos/toxicidade
Benzoxepinas/isolamento & purificação
Benzoxepinas/toxicidade
Biomarcadores/metabolismo
Neoplasias Encefálicas/metabolismo
Neoplasias Encefálicas/patologia
Ácidos Carboxílicos/isolamento & purificação
Ácidos Carboxílicos/toxicidade
Linhagem Celular Tumoral
Proliferação Celular/efeitos dos fármacos
Córtex Cerebral/metabolismo
Dano ao DNA
Desoxiguanosina/análogos & derivados
Desoxiguanosina/metabolismo
Dibenzoxepinas/isolamento & purificação
Dibenzoxepinas/toxicidade
Relação Dose-Resposta a Droga
Glioblastoma/metabolismo
Glioblastoma/patologia
Seres Humanos
L-Lactato Desidrogenase/metabolismo
Líquens/química
Neurônios/metabolismo
Neurônios/patologia
Estresse Oxidativo/efeitos dos fármacos
Extratos Vegetais/isolamento & purificação
Extratos Vegetais/toxicidade
Ratos Sprague-Dawley
Salicilatos/isolamento & purificação
Salicilatos/toxicidade
Fatores de Tempo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antineoplastic Agents, Phytogenic); 0 (Benzoxepins); 0 (Biomarkers); 0 (Carboxylic Acids); 0 (Dibenzoxepins); 0 (Plant Extracts); 0 (Salicylates); 0 (olivetoric acid); 0 (psoromic acid); 88847-89-6 (8-oxo-7-hydrodeoxyguanosine); EC 1.1.1.27 (L-Lactate Dehydrogenase); G9481N71RO (Deoxyguanosine); X901BNT6BF (physodic acid)
[Em] Mês de entrada:1702
[Cu] Atualização por classe:170213
[Lr] Data última revisão:
170213
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:151226
[St] Status:MEDLINE
[do] DOI:10.3109/13880209.2015.1126620


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[PMID]:26342621
[Au] Autor:Latkowska E; Bober B; Chrapusta E; Adamski M; Kaminski A; Bialczyk J
[Ad] Endereço:Department of Plant Physiology and Development, Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, Gronostajowa 7 St., 30-387 Kraków, Poland. Electronic address: ewa.latkowska@uj.edu.pl.
[Ti] Título:Secondary metabolites of the lichen Hypogymnia physodes (L.) Nyl. and their presence in spruce (Picea abies (L.) H. Karst.) bark.
[So] Source:Phytochemistry;118:116-23, 2015 Oct.
[Is] ISSN:1873-3700
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Lichen species typically have a characteristic profile of secondary metabolites. Dense populations of Hypogymnia physodes growing frequently as epiphytes on tree branches have harmful effects on the host, likely due to their secondary compounds, which were undetected in tree tissues until now. The aim of the present study was to re-characterise the suite of secondary metabolites of H. physodes thalli and to estimate their translocation into spruce (Picea abies) bark. Thallus and bark extracts were compared using ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). The compounds were identified based on their UV, MS and MS/MS spectra as well as retention factors of their TLC analysis. In addition to the previously described secondary metabolites (protocetraric, physodalic, 3-hydroxyphysodic, physodic, and 2'-O-methylphysodic acids, atranorin and chloroatranorin) of H. physodes, further three were identified in its thalli: conphysodalic, 4-O-methylphysodic and α-alectoronic acids. Fragmentation patterns from the negative ionisation of each compound were proposed, some of which were described for the first time. Among all of the detected lichen substances, a few, e.g., physodalic, 3-hydroxyphysodic, physodic acids and atranorin, were present in the bark of spruce branches that were abundantly colonised by lichen. The newly identified compounds of H. physodes thalli may belong to its constant or accessory secondary metabolites. These compounds may be useful in the chemotaxonomic classification of this species. The presence of some lichen substances in spruce bark confirmed their ability to penetrate host tissues. These data suggest that H. physodes compounds may cause long-term effects on spruces in nature.
[Mh] Termos MeSH primário: Abies/química
Líquens/química
Picea/química
Casca de Planta/química
[Mh] Termos MeSH secundário: Dibenzoxepinas/análise
Estrutura Molecular
Espectrometria de Massas em Tandem
Árvores/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Dibenzoxepins); X901BNT6BF (physodic acid)
[Em] Mês de entrada:1606
[Cu] Atualização por classe:151003
[Lr] Data última revisão:
151003
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150907
[St] Status:MEDLINE


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[PMID]:25735543
[Au] Autor:Stopka T; Marzo L; Zurro M; Janich S; Würthwein EU; Daniliuc CG; Alemán J; Mancheño OG
[Ad] Endereço:Organisch-Chemisches Institut, Universität Münster, 48149 Münster (Germany).
[Ti] Título:Oxidative C-H bond functionalization and ring expansion with TMSCHN2 : a copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines.
[So] Source:Angew Chem Int Ed Engl;54(17):5049-53, 2015 Apr 20.
[Is] ISSN:1521-3773
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative CH bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way.
[Mh] Termos MeSH primário: Azepinas/química
Cobre/química
Diazometano/análogos & derivados
Compostos de Trimetilsilil/química
[Mh] Termos MeSH secundário: Carbono/química
Catálise
Complexos de Coordenação/química
Diazometano/química
Dibenzoxepinas/química
Hidrogênio/química
Oxirredução
Termodinâmica
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Azepines); 0 (Coordination Complexes); 0 (Dibenzoxepins); 0 (Trimethylsilyl Compounds); 60A625P70P (Diazomethane); 7440-44-0 (Carbon); 789U1901C5 (Copper); 7YNJ3PO35Z (Hydrogen); QI98HQO8C4 (trimethylsilyldiazomethane)
[Em] Mês de entrada:1601
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150305
[St] Status:MEDLINE
[do] DOI:10.1002/anie.201411726


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[PMID]:25592003
[Au] Autor:Tanizaki H; Yamamoto Y; Nakamizo S; Otsuka A; Miyachi Y; Kabashima K
[Ad] Endereço:Department of Dermatology, Kyoto University Graduate School of Medicine, Kyoto, Japan.
[Ti] Título:Comparison of the efficacy of olopatadine and fexofenadine in chronic idiopathic urticaria patients: a crossover study.
[So] Source:Pharmacology;95(1-2):32-5, 2015.
[Is] ISSN:1423-0313
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Olopatadine is one of the second-generation H1 antihistamines that were used for treating allergic disorders initially in Asia, and now also in Western countries. Whereas several trials compared the efficacy on chronic urticaria among second-generation H1 antihistamines, no study has directly compared the clinical efficacy between olopatadine and other H1 antihistamines in patients with chronic idiopathic urticaria (CIU). In this study, we address this issue for the first time and conclude that olopatadine is a good candidate for the treatment of CIU.
[Mh] Termos MeSH primário: Antialérgicos/uso terapêutico
Dibenzoxepinas/uso terapêutico
Antagonistas dos Receptores Histamínicos H1 não Sedativos/uso terapêutico
Terfenadina/análogos & derivados
Urticária/tratamento farmacológico
[Mh] Termos MeSH secundário: Adulto
Doença Crônica
Estudos Cross-Over
Feminino
Seres Humanos
Masculino
Meia-Idade
Cloridrato de Olopatadina
Terfenadina/uso terapêutico
Resultado do Tratamento
[Pt] Tipo de publicação:JOURNAL ARTICLE; RANDOMIZED CONTROLLED TRIAL
[Nm] Nome de substância:
0 (Anti-Allergic Agents); 0 (Dibenzoxepins); 0 (Histamine H1 Antagonists, Non-Sedating); 2XG66W44KF (Olopatadine Hydrochloride); 7BA5G9Y06Q (Terfenadine); E6582LOH6V (fexofenadine)
[Em] Mês de entrada:1510
[Cu] Atualização por classe:151119
[Lr] Data última revisão:
151119
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150117
[St] Status:MEDLINE
[do] DOI:10.1159/000370312



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