Base de dados : MEDLINE Pesquisa : B01.650.940.800.575.912.250.859.500.750 [Categoria DeCS] Referências encontradas : 135 [refinar] Mostrando: 1 .. 10   no formato [Detalhado]

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[PMID]: 28966277 [Au] Autor: Terazawa S; Uemura Y; Koyama Y; Kawakami S; Sugimoto S; Matsunami K; Otsuka H; Shinzato T; Kawahata M; Yamaguchi K [Ad] Endereço: Graduate School of Biomedical and Health Sciences, Hiroshima University. [Ti] Título: Microtropins Q-W, ent-Labdane Glucosides: Microtropiosides G-I, Ursane-Type Triterpene Diglucoside and Flavonol Glycoside from the Leaves of Microtropis japonica. [So] Source: Chem Pharm Bull (Tokyo);65(10):930-939, 2017. [Is] ISSN: 1347-5223 [Cp] País de publicação: Japan [La] Idioma: eng [Ab] Resumo: Microtropins Q-W, (2S,3R)-2-ethyl-2,3-dihydroxybutyrate of various glucosides and glucose, as well as three ent-labdane diterpenoid glucosides, named microtropiosides G, H and I, an ursane-type triterpene diglucoside and a flavonoid glycoside were isolated from the MeOH extract of the leaves of Microtropis japonica. The structure of microtropioside A, also isolated from the branches of M. japonica, was elucidated spectroscopically in a previous experiment and was found to possess a rare seven-membered oxyrane ring. Its structure was confirmed by X-ray crystallographic analysis of its pentaacetate. [Mh] Termos MeSH primário: Celastraceae/química Flavonóis/química Glucosídeos/química Triterpenos/química [Mh] Termos MeSH secundário: Celastraceae/metabolismo Cristalografia por Raios X Diterpenos/química Flavonóis/isolamento & purificação Glucosídeos/isolamento & purificação Espectroscopia de Ressonância Magnética Conformação Molecular Extratos Vegetais/química Folhas de Planta/química Folhas de Planta/metabolismo Triterpenos/isolamento & purificação [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Diterpenes); 0 (Flavonols); 0 (Glucosides); 0 (Plant Extracts); 0 (Triterpenes); 0 (labdane); 0 (ursane) [Em] Mês de entrada: 1710 [Cu] Atualização por classe: 171030 [Lr] Data última revisão: 171030 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 171003 [St] Status: MEDLINE [do] DOI: 10.1248/cpb.c17-00459

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[PMID]: 28666142 [Au] Autor: Callies O; Núñez MJ; Perestelo NR; Reyes CP; Torres-Romero D; Jiménez IA; Bazzocchi IL [Ad] Endereço: Instituto Universitario de Bio-Orgánica Antonio González, Departamento de Química Orgánica, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain. [Ti] Título: Distinct sesquiterpene pyridine alkaloids from in Salvadoran and Peruvian Celastraceae species. [So] Source: Phytochemistry;142:21-29, 2017 Oct. [Is] ISSN: 1873-3700 [Cp] País de publicação: England [La] Idioma: eng [Ab] Resumo: As part of a bioprospecting program aimed at the discovery of undescribed natural products from Salvadoran and Peruvian flora, the phytochemical investigations of four Celastraceae species, Celastrus vulcanicola, Maytenus segoviarum, Maytenus jeslkii, and Maytenus cuzcoina, were performed. The current study reports the isolation and structural characterization of five previously undescribed macrolide sesquiterpene pyridine alkaloids, named vulcanicoline-A, cuzcoinine, vulcanicoline-B, jelskiine, and vulcanicoline-C, along with sixteen known alkaloids. The structures of the alkaloids were established by spectrometric and extensive 1D and 2D NMR spectroscopic analysis, including COSY, HSQC, HMBC, and ROESY experiments. The absolute configurations of alkaloids were proposed based on optical rotation sign, and biogenetic considerations. This study represents the first phytochemical analysis of Maytenus segoviarum. [Mh] Termos MeSH primário: Alcaloides/isolamento & purificação Celastraceae/química Piridinas/isolamento & purificação Sesquiterpenos/isolamento & purificação [Mh] Termos MeSH secundário: Alcaloides/química Celastrus El Salvador Maytenus/química Estrutura Molecular Ressonância Magnética Nuclear Biomolecular Peru Piridinas/química Sesquiterpenos/química [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Alkaloids); 0 (Pyridines); 0 (Sesquiterpenes) [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: 170701 [St] Status: MEDLINE

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[PMID]: 28476411 [Au] Autor: Ochieng CO; Opiyo SA; Mureka EW; Ishola IO [Ad] Endereço: Department of Chemistry, Maseno University, Private Bag, 40105, Maseno, Kenya. Electronic address: otieno.charles9@gmail.com. [Ti] Título: Cyclooxygenase inhibitory compounds from Gymnosporia heterophylla aerial parts. [So] Source: Fitoterapia;119:168-174, 2017 Jun. [Is] ISSN: 1873-6971 [Cp] País de publicação: Netherlands [La] Idioma: eng [Ab] Resumo: Gymnosporia heterophylla (Celastraceae) is an African medicinal plants used to treat painful and inflammatory diseases with partial scientific validation. Solvent extractions followed by repeated chromatographic purification of the G. heterophylla aerial parts led to the isolation of one new ß-dihydroagarofuran sesquiterpene alkaloid (1), and two triterpenes (2-3). In addition, eight known compounds including one ß-dihydroagarofuran sesquiterpene alkaloid (4), and six triterpenes (5-10) were isolated. All structures were determined through extensive analysis of the NMR an MS data as well as by comparison with literature data. These compounds were evaluated for the anti-inflammatory activities against COX-1 and -2 inhibitory potentials. Most of the compound isolated showed non selective COX inhibitions except for 3-Acetoxy-1ß-hydroxyLupe-20(29)-ene (5), Lup-20(29)-ene-1ß,3ß-diol (6) which showed COX-2 selective inhibition at 0.54 (1.85), and 0.45 (2.22) IC , in mM (Selective Index), respectively. The results confirmed the presence of anti-inflammatory compounds in G. heterophylla which are important indicators for development of complementary medicine for inflammatory reactions; however, few could be useful as selective COX-2 inhibitor. [Mh] Termos MeSH primário: Alcaloides/química Celastraceae/química Inibidores de Ciclo-Oxigenase/química Sesquiterpenos/química Triterpenos/química [Mh] Termos MeSH secundário: Alcaloides/isolamento & purificação Inibidores de Ciclo-Oxigenase/isolamento & purificação Estrutura Molecular Componentes Aéreos da Planta/química Extratos Vegetais/química Plantas Medicinais/química Sesquiterpenos/isolamento & purificação Triterpenos/isolamento & purificação [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Alkaloids); 0 (Cyclooxygenase Inhibitors); 0 (Plant Extracts); 0 (Sesquiterpenes); 0 (Triterpenes); 20053-66-1 (dihydroagarofuran) [Em] Mês de entrada: 1706 [Cu] Atualização por classe: 170615 [Lr] Data última revisão: 170615 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 170507 [St] Status: MEDLINE

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[PMID]: 28434194 [Au] Autor: Zhang XW; Wang KW; Zhou MQ [Ad] Endereço: Department of Food Science and Nutrition, University of Jinan, Jinan, 250022, P. R. China. [Ti] Título: Cytotoxic Triterpenoids from the Stalks of Microtropis triflora. [So] Source: Chem Biodivers;14(7), 2017 Jul. [Is] ISSN: 1612-1880 [Cp] País de publicação: Switzerland [La] Idioma: eng [Ab] Resumo: Bioassay-guided phytochemical investigation of the stalks of Microtropis triflora Merr. & F.L. Freeman led to the isolation of ten triterpenes 1 - 10, including one novel compound 3,24-epoxy-2α,24-dihydroxyfriedelan-29-oic acid (1). Their chemical structures were identified on the basis of spectroscopic analysis, including HR-ESI mass spectrometry, 1D- and 2D-NMR ( H, C, H, H-COSY, HSQC, HMBC, and NOESY), and by comparison with the data reported. The cytotoxicities of compounds 1 - 10 against a panel of cultured human tumor cell lines (Bcap37, SMMC7721, HeLa, CNE) were evaluated. The new compound 1 showed moderate anti-tumor activities with IC values of 39.22, 29.24, 23.28, and 68.81 µm/ml, respectively. These results might be helpful for explaining the use of M. triflora in traditional medicine. Triterpenes are characteristic of Microtropis genus and could be useful as potential chemotaxonomic markers. [Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/isolamento & purificação Celastraceae/química Triterpenos/isolamento & purificação [Mh] Termos MeSH secundário: Antineoplásicos Fitogênicos/química Antineoplásicos Fitogênicos/farmacologia Linhagem Celular Tumoral Citotoxinas/isolamento & purificação Seres Humanos Espectroscopia de Ressonância Magnética Estrutura Molecular Compostos Fitoquímicos/isolamento & purificação Espectrometria de Massas por Ionização por Electrospray Triterpenos/química Triterpenos/farmacologia [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Antineoplastic Agents, Phytogenic); 0 (Cytotoxins); 0 (Phytochemicals); 0 (Triterpenes) [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: 170424 [St] Status: MEDLINE [do] DOI: 10.1002/cbdv.201700066

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[PMID]: 28241818 [Au] Autor: Elisha IL; Botha FS; McGaw LJ; Eloff JN [Ad] Endereço: Phytomedicine Programme, Department of Paraclinical Sciences, Faculty of Veterinary Science, University of Pretoria, Private Bag X04, Onderstepoort, 0110, Pretoria, South Africa. [Ti] Título: The antibacterial activity of extracts of nine plant species with good activity against Escherichia coli against five other bacteria and cytotoxicity of extracts. [So] Source: BMC Complement Altern Med;17(1):133, 2017 Feb 28. [Is] ISSN: 1472-6882 [Cp] País de publicação: England [La] Idioma: eng [Ab] Resumo: BACKGROUND: The development of antibiotic resistant bacteria stems from a number of factors, including inappropriate use of antibiotics in human and animal health and their prolonged use as growth promoters at sub-clinical doses in poultry and livestock production. We were interested in investigating plants that could be useful in protecting humans or animals against diarrhoea. We decided to work on extracts of nine plant species with good activity against Escherichia coli based on earlier work in the Phytomedicine Programme. Leaves of nine medicinal plant species with high antibacterial activity against Escherichia coli were extracted with acetone and their minimal inhibitory concentration (MIC) values determined using a microplate serial dilution technique against Gram-positive (Staphylococcus aureus, Enterococcus faecalis and Bacillus cereus) and Gram-negative (Escherichia coli, Salmonella Typhimurium and Pseudomonas aeruginosa) bacteria. Bioautography was used to determine the number of bioactive compounds in each extract. In vitro safety of the extracts was determined using the 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide reduction assay on Vero cells. RESULTS: The extracts were active against all the pathogens with average MICs ranging from 0.02 to 0.52 mg/ml. As expected E. coli was relatively sensitive, while E. faecalis and S. Typhimurium were more resistant to the extracts (average MICs of 0.28 mg/ml and 0.22 mg/ml respectively). Cremaspora triflora and Maesa lanceolata leaf extracts had higher activity than the other extracts against Gram-positive and Gram-negative pathogens with mean MICs of 0.07 mg/ml and 0.09 mg/ml respectively. Extracts of Maesa lanceolata and Hypericum roeperianum had the highest total antibacterial activity (TAA) at 1417 and 963 ml/g respectively. All extracts with the exception of that of Maesa lanceolata, Elaeodendron croceum and Calpurnia aurea had relatively low cytotoxicity with LC > 20 µg/ml. Cremaspora triflora had the best selectivity index (SI) against S. aureus and E. coli of 2.87 and 1.15 respectively. Hypericum roeperianum had a SI of 1.10 against B. cereus. Bioautography revealed 1-6 visible antimicrobial compounds that were generally non-polar. CONCLUSIONS: There was a weak positive, but statistically non-significant correlation between the potency of the extracts and their cytotoxicity (R = 0.45, ρ > 0.05). The activity of the extracts on the test bacteria was in some cases not correlated with cytotoxicity, as shown by selectivity indices >1. This means that cellular toxicity was probably not due to compounds with antibacterial activity. Some of the extracts had a good potential for therapeutic use against the bacterial pathogens or for application in treating diarhoea. It does not appear that activity against E. coli is a good predictor of activity against Gram-negative rather than Gram-positive bacteria. Further investigation is in progress on C. triflora and H. roeperianum, both of which had promising activities and potential safety based on cytotoxicity. [Mh] Termos MeSH primário: Antibacterianos/farmacologia Bacillus cereus/efeitos dos fármacos Enterococcus faecalis/efeitos dos fármacos Extratos Vegetais/farmacologia Pseudomonas/efeitos dos fármacos Salmonella typhimurium/efeitos dos fármacos Staphylococcus aureus/efeitos dos fármacos [Mh] Termos MeSH secundário: Animais Antibacterianos/efeitos adversos Bacillus cereus/crescimento & desenvolvimento Celastraceae Cercopithecus aethiops Diarreia/microbiologia Enterococcus faecalis/crescimento & desenvolvimento Escherichia coli/efeitos dos fármacos Escherichia coli/crescimento & desenvolvimento Hypericum Myrsinaceae Extratos Vegetais/efeitos adversos Pseudomonas/crescimento & desenvolvimento Rubiaceae Salmonella typhimurium/crescimento & desenvolvimento Staphylococcus aureus/crescimento & desenvolvimento Células Vero [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Anti-Bacterial Agents); 0 (Plant Extracts) [Em] Mês de entrada: 1703 [Cu] Atualização por classe: 170317 [Lr] Data última revisão: 170317 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 170301 [St] Status: MEDLINE [do] DOI: 10.1186/s12906-017-1645-z

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[PMID]: 28125664 [Au] Autor: Skuhrovec J; Stejskal R; Trnka F; di Giulio A [Ad] Endereço: Group Function of Invertebrate and Plant Biodiversity in Agro-Ecosystems, Crop Research Institute, Praha 6 - Ruzyne, Czech Republic. [Ti] Título: Velcro-Like System Used to Fix a Protective Faecal Shield on Weevil Larvae. [So] Source: PLoS One;12(1):e0170800, 2017. [Is] ISSN: 1932-6203 [Cp] País de publicação: United States [La] Idioma: eng [Ab] Resumo: The last instar larva and pupa of Eucoeliodes mirabilis (A. Villa & G. B. Villa, 1835) (Curculionidae: Ceutorhynchini) are described using drawings and SEM images and are compared and keyed with already described larvae of 58 other ceutorhynchinae taxa. The larval body has an effective combination of morphological adaptations that assist a unique biological defensive strategy. All larval stages of E. mirabilis feed ectophytically on leaves of Euonymus europaeus L. (Celastraceae), and the larval body is covered with a thick faecal shield. The fixation of this protective shield on the larval back is performed by a peculiar dorsal microsculpture composed of a dense carpet of microtrichia on the thorax and abdomen, which serves effectively as a velcro system. Because of this strategy, macrosetae on the larval and pupal body of E. mirabilis are completely reduced. Larvae of E. mirabilis also have distinct morphological adaptations for protecting the spiracles against intrusion of faeces and avoiding occlusion of the tracheal system: a) microtrichia around spiracles are slightly shorter, distinctly stronger and are arranged with high-density and in clusters and b) spiracles are protected by an external safety valve. This strategy of E. mirabilis larvae is unique, although somewhat similar to that of Criocerinae and Blepharida-group leave beetles (Galerucinae) (both Coleoptera: Chrysomelidae), but with distinctly different morphological adaptations. [Mh] Termos MeSH primário: Adaptação Fisiológica Larva/anatomia & histologia Pupa/anatomia & histologia Gorgulhos/anatomia & histologia [Mh] Termos MeSH secundário: Animais Celastraceae/parasitologia República Tcheca Fezes Feminino Larva/fisiologia Larva/ultraestrutura Masculino Folhas de Planta/parasitologia Pupa/fisiologia Pupa/ultraestrutura Gorgulhos/fisiologia Gorgulhos/ultraestrutura [Pt] Tipo de publicação: JOURNAL ARTICLE [Em] Mês de entrada: 1708 [Cu] Atualização por classe: 170810 [Lr] Data última revisão: 170810 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 170127 [St] Status: MEDLINE [do] DOI: 10.1371/journal.pone.0170800

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[PMID]: 28852732 [Au] Autor: Roca-Mézquita C; Graniel-Sabido M; Moo-Puc RE; Leon-Déniz LV; Gamboa-León R; Arjona-Ruiz C; Tun-Garrido J; Mirón-López G; Mena-Rejón GJ [Ad] Endereço: Facultad de Química, Universidad Autónoma de Yucatán, C. 41 No. 421 Col. Industrial, C.P. 97150, Mérida, Yucatán, México. [Ti] Título: ANTIPROTOZOAL ACTIVITY OF EXTRACTS OF (CELASTRACEAE). [So] Source: Afr J Tradit Complement Altern Med;13(4):162-165, 2016. [Is] ISSN: 2505-0044 [Cp] País de publicação: Nigeria [La] Idioma: eng [Ab] Resumo: BACKGROUND: Chagas disease, amebiasis, giardiasis and trichomoniasis represent a serious health problem in Latin America. The drugs employed to treat these illnesses produce important side effects and resistant strains have appeared. The present study was aimed to evaluate the antiprotozoal activity of leaves, stem bark and root bark of , a celastraceus, that is used in Mexico as an anti-infective in febrile-type diseases. MATERIALS AND METHODS: Dichloromethane and methanol extracts of leaves, bark and roots of were tested against , , , and . A quantitative HPLC analysis of pristimerin and tingenone was performed. RESULTS: The dichloromethane extract of roots was active against , , , and , at IC50's of 0.80, 0.44, 0.46, and 2.68 µg/mL, respectively. The HPLC analysis revealed the presence of tingenone (3.84%) and pristimerin (0.14%). CONCLUSIONS: The dichloromethane extract of the roots bark showed significant activity against all screened protozoa. [Mh] Termos MeSH primário: Antiprotozoários/farmacologia Celastraceae/química Extratos Vegetais/farmacologia [Mh] Termos MeSH secundário: Antiprotozoários/isolamento & purificação Entamoeba histolytica/efeitos dos fármacos Giardia lamblia/efeitos dos fármacos México Testes de Sensibilidade Parasitária Casca de Planta/química Extratos Vegetais/isolamento & purificação Folhas de Planta/química Raízes de Plantas/química Trypanosoma cruzi/efeitos dos fármacos [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Antiprotozoal Agents); 0 (Plant Extracts) [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: 170831 [St] Status: MEDLINE [do] DOI: 10.21010/ajtcam.v13i4.21

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[PMID]: 27521896 [Au] Autor: Eckelmann D; Kusari S; Spiteller M [Ad] Endereço: Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany. [Ti] Título: Occurrence and spatial distribution of maytansinoids in Putterlickia pyracantha, an unexplored resource of anticancer compounds. [So] Source: Fitoterapia;113:175-81, 2016 Sep. [Is] ISSN: 1873-6971 [Cp] País de publicação: Netherlands [La] Idioma: eng [Ab] Resumo: Maytansinoids possess remarkable antibiotic activities along with high cytotoxicity, many of which are currently used (or in clinical trials) in the treatment of breast cancer. Celastraceous plants and their associated microorganisms serve as an important resource of maytansinoids. Here, we report the occurrence and structural elucidation of several maytansinoids in Putterlickia pyracantha plants bioprospected in South Africa. In addition to maytansine, which is already known to be present in this species, we show the presence of maytanprine, maytanbutine, maytanvaline, normaytancyprine and an abundant maytansine precursor in different tissues using high-resolution mass spectrometry. Furthermore, we identified two new hydroxylated maytansinoids by HRMS(2) analyses. We also employed MALDI-imaging-HRMS to study the spatial distribution and localization of the maytansinoids within the different plant tissues. On the one hand, the fragmentation pathways of the maytansinoids we report herein using HRMS(n) will allow quick identification of these compounds in the future without isolating from the natural resources. On the other hand, MALDI-imaging-HRMS revealed insights into the plausible ecological roles and biosynthetic pathways of these compounds in P. pyracantha plants. [Mh] Termos MeSH primário: Celastraceae/química Maitansina/química [Mh] Termos MeSH secundário: Maitansina/análogos & derivados Maitansina/isolamento & purificação Estrutura Molecular Metabolismo Secundário Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 14083FR882 (Maytansine); 38997-09-0 (maytanprine) [Em] Mês de entrada: 1701 [Cu] Atualização por classe: 170131 [Lr] Data última revisão: 170131 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 160814 [St] Status: MEDLINE

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[PMID]: 27469098 [Au] Autor: Kaweetripob W; Mahidol C; Thongnest S; Prawat H; Ruchirawat S [Ad] Endereço: Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand. [Ti] Título: Polyoxygenated ursane and oleanane triterpenes from Siphonodon celastrineus. [So] Source: Phytochemistry;129:58-67, 2016 Sep. [Is] ISSN: 1873-3700 [Cp] País de publicação: England [La] Idioma: eng [Ab] Resumo: Twenty polyoxygenated triterpenes, including nineteen ursanes and one oleanane, were characterized from the stem material of Siphonodon celastrineus (Celastraceae) through the application of spectroscopic techniques and chemical transformation. Three of the ursane-type triterpenoids possessed the rare 13,27-cyclopropane ring skeleton. [Mh] Termos MeSH primário: Antineoplásicos Fitogênicos/isolamento & purificação Celastraceae/química Ácido Oleanólico/isolamento & purificação Triterpenos/isolamento & purificação [Mh] Termos MeSH secundário: Antineoplásicos Fitogênicos/química Antineoplásicos Fitogênicos/farmacologia Ensaios de Seleção de Medicamentos Antitumorais Estrutura Molecular Ácido Oleanólico/análogos & derivados Ácido Oleanólico/química Ácido Oleanólico/farmacologia Caules de Planta/química Triterpenos/química Triterpenos/farmacologia [Pt] Tipo de publicação: JOURNAL ARTICLE [Nm] Nome de substância: 0 (Antineoplastic Agents, Phytogenic); 0 (Triterpenes); 0 (oleanane); 0 (ursane); 6SMK8R7TGJ (Oleanolic Acid) [Em] Mês de entrada: 1702 [Cu] Atualização por classe: 170224 [Lr] Data última revisão: 170224 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 160730 [St] Status: MEDLINE

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[PMID]: 26854381 [Au] Autor: Núñez MJ; Jiménez IA; Mendoza CR; Chavez-Sifontes M; Martinez ML; Ichiishi E; Tokuda R; Tokuda H; Bazzocchi IL [Ad] Endereço: Instituto Universitario de Bio-Orgánica "Antonio González", Departamento de Química Orgánica, Universidad de La Laguna and Instituto Canario de Investigación del Cáncer, Avenida Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain; Laboratorio de Investigación en Productos Naturales, Fa [Ti] Título: Dihydro-ß-agarofuran sesquiterpenes from celastraceae species as anti-tumour-promoting agents: Structure-activity relationship. [So] Source: Eur J Med Chem;111:95-102, 2016 Mar 23. [Is] ISSN: 1768-3254 [Cp] País de publicação: France [La] Idioma: eng [Ab] Resumo: Inhibition of tumour promotion in multistage chemical carcinogenesis is considered a promising strategy for cancer chemoprevention. In an ongoing investigation of bioactive secondary metabolites from Celastraceae species, five new dihydro-ß-agarofuran sesquiterpenes (1-5), named Chiapens A-E, and seventeen known ones, were isolated from Maytenus chiapensis. Their structures were elucidated by extensive NMR spectroscopic and mass spectrometric techniques, and their absolute configurations were determined by circular dichroism studies, chemical correlations and biogenic means. The isolated compounds, along with twenty known sesquiterpenes, previously isolated from Zinowiewia costaricensis, have been tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorpol-13-acetate (TPA). Thirty three compounds from this series showed stronger effects than that of ß-carotene, the reference inhibitor. The structure-activity relationship (SAR) analysis revealed that the type of substituent, in particular at the C-1 position of the sesquiterpene scaffold, was able to modulate the anti-tumour promoting activity. Compounds 3, 6, and 33 showed significant effects in an in vivo two-stage mouse-skin carcinogenesis model. [Mh] Termos MeSH primário: Antineoplásicos/química Antineoplásicos/farmacologia Celastraceae/química Papiloma/tratamento farmacológico Sesquiterpenos/química Sesquiterpenos/farmacologia [Mh] Termos MeSH secundário: Animais Antígenos Virais/metabolismo Antineoplásicos/síntese química Linhagem Celular Tumoral Proliferação Celular/efeitos dos fármacos Relação Dose-Resposta a Droga Ensaios de Seleção de Medicamentos Antitumorais Feminino Seres Humanos Camundongos Camundongos Endogâmicos ICR Modelos Moleculares Estrutura Molecular Papiloma/metabolismo Papiloma/patologia Sesquiterpenos/síntese química Relação Estrutura-Atividade Acetato de Tetradecanoilforbol/análogos & derivados Acetato de Tetradecanoilforbol/antagonistas & inibidores Acetato de Tetradecanoilforbol/farmacologia [Pt] Tipo de publicação: JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T [Nm] Nome de substância: 0 (12-O-tetradecanoylphorbol-1,3-acetate); 0 (Antigens, Viral); 0 (Antineoplastic Agents); 0 (Epstein-Barr virus early antigen); 0 (Sesquiterpenes); 20053-66-1 (dihydroagarofuran); NI40JAQ945 (Tetradecanoylphorbol Acetate) [Em] Mês de entrada: 1611 [Cu] Atualização por classe: 161230 [Lr] Data última revisão: 161230 [Sb] Subgrupo de revista: IM [Da] Data de entrada para processamento: 160209 [St] Status: MEDLINE

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