Navegando por Autor "Silva, Grácia Divina de Fátima"

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3-beta-(Stearyloxy)olean-12-ene from Austroplenckia populnea : structure elucidation by 2D-NMR and quantitative 13C-NMR spectroscopy.
(2003) Vieira Filho, Sidney Augusto; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Howarth, O. W.; Lula, Ivana Silva
3 -(Stearyloxy)olean-12-ene was isolated from a hexane extract of Austroplenckia populnea Reiss (Celastraceae) leaves. The structure was solved by means of quantitative 13C-NMR, HMBC, HMQC, COSY, NOESY, and NOE difference spectra. The mass spectrum showed an [M 1] ion peak at m/z 693, and the molecular formula C48H84O2 was confirmed by combustion analysis.
Algistatic effect of a quinonamethide triterpene on Microcystis novacekii.
(2013) Silva, Fernando César; Guedes, Fernanda Alves de Freitas; Franco, Maione Wittig; Barbosa, Francisco Antônio Rodrigues; Marra, Camila Antunes; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto
Cyanobacteria proliferation represents a problem to water treatment for human consumption supply. Species of the genus Microcystis, commonly found in continental waters, can bloom and produce microcystine and other toxic compounds associated to human and animal poisoning, depending on the nutrient levels present in the water. The use of natural products to control cyanobacteria blooms is promising since they are less harmful to the environment than compounds obtained by organic syntheses. Triterpenes, which are associated with several biological activities, have been isolated from species of the genus Maytenus (Celastraceae), commonly found in Cerrado regions of Brazil. Tingenone is a pentacyclic triterpene that has cytotoxic properties and induces growth inhibition in some microorganisms. In this study, the effects of tingenone isolated from Maytenus gonoclada at distinct concentrations (e.g., 50, 150, 500, 1,500, and 4,500 μg L−1) on the growth rates of Microcystis novacekii was investigated. The algicide activity was verified using M. novacekii cultures growing in ASM1 culture medium at 23 °C and continuous illumination for 96 h. Growth inhibition was monitored by light microscopy and optical density (OD680 nm). The median effective concentration associated to the M. novacekii inhibition growth induced by tingenone was 12.2 μg L−1. The result indicates that tingenone has algicide effect and can be potentially applied in water management for public supply, replacing synthetic algicides.
Anti-inflammatory, antimicrobial and acetylcholinesterase inhibitory activities of friedelanes from Maytenus robusta branches and isolation of further triterpenoids.
(2017) Sousa, Grasiely Faria de; Aguilar, Mariana Guerra de; Dias, Danielle Ferreira; Takahashi, Jacqueline Aparecida; Moreira, Maria Eliza de Castro; Vieira Filho, Sidney Augusto; Silva, Grácia Divina de Fátima; Rodrigues, Salomão Bento Vasconcelos; Messias, Maria Cristina Teixeira Braga; Duarte, Lucienir Pains
The new pentacyclic triterpenoids friedel-1-en-3,16-dione (1), 1α,29-dihydroxyfriedelan-3-one (2) and 16β,28,29-trihydroxyfriedelan-3-one (3) were isolated from Maytenus robusta branches in addition to the known, but new for this species, triterpenoid 12α,29-dihydroxyfriedelan-3-one (4). The structures and stereochemistry of the novel triterpenoids were established by IR, 1D/2D NMR and HR-APCIMS spectral data. In addition, the biological activity of compound 2 and the previously isolated friedelanes 5–8 (friedelan-3,16-dione, 29-hydroxyfriedelan- 3-one, 29-hydroxyfriedelan-3,16-dione and 16β,29-dihydroxyfriedelan-3-one) was investigated. Compounds 2 and 8 were tested for their acetylcholinesterase properties and antimicrobial activity against the bacteria Staphylococcus aureus, Pseudomonas aeruginosa, Listeria monocytogenes, Citrobacter freundii, and the fungus Candida albicans. Compound 2 was the most active compound for both assays, with values of 32.3% acetylcholinesterase inhibition, 42% activity against the fungus Candida albicans and 34% against the bacterium Pseudomonas aeruginosa. Compounds 5–8 were assayed for their antiedematogenic activity using the carrageenan- induced paw edema assay. At maximum inflammation after three hours, compounds 6 and 8 showed 42% and 57% activity, respectively. After four hours, compounds 5 and 7 showed activity of 71% and 75% compared to 79% of the control indomethacin.
Anti-trypanosomal activity of pentacyclic triterpenes isolated from Austroplenckia populnea (Celastraceae).
(2002) Duarte, Lucienir Pains; Vieira Filho, Sidney Augusto; Silva, Grácia Divina de Fátima; Sousa, José Rego de; Pinto, Artur da Silveira
Four pentacyclic triterpenes isolated from Austroplenckia populnea and four compounds of known anti T. cruzi or anti-malarial activity were tested. Of those triterpenes tested 20_-hydroxy-tingenone showed high activity, epikatonic acid was less active, while populnilic and populninic acids were inactive against the trypanosome of the subgenus Schizotrypanum tested. Benzonidazole, nifurtimox, ketoconazole and primaquine presented a remarkable dose-dependent inhibitory effect reaching practically to a total growth inhibition of the parasite at the end of incubation time. The trypanosome tested appear to be a suitable model for preliminary screen for anti T. (S.) cruzi compounds.
Antigiardial activity of the hexane extract of Maytenus gonoclada mart.
(2012) Silva, Fernando César; Busatti, Haendel Gonçalves Nogueira Oliveira; Gomes, Maria Aparecida; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto
Plants of the Maytenus genus have been used in folk medicine in Brazil for treatment of gastrointestinal motility disturbances such as diarrhea. The present study was performed to evaluate antigiardial activity of the hexane extract and triterpenes isolated from the branches of Maytenus gonoclada Mart. (Celastraceae). The hexane extract and triterpenes were examined for antigiardial activity using the colorimetric method against Giardia lamblia (ATCC 30888). The hexane extract exhibited antigiardial activity. This result may partly explain and support the use of plants of the Maytenus genus for the treatment of diarrhea in folk medicine in Brazil.
Antimicrobial activity of synthetic bornyl benzoates against Trypanosoma cruzi.
(2012) Corrêa, Paulo Roberto Ceridóreo; Miranda, Roqueline Rodrigues Silva de; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto; Okuma, Adriana Akemi; Carazza, Fernando; Díaz, José Andrés Morgado; Pinge Filho, Phileno; Yamauchi, Lucy Megumi; Nakamura, Celso Vataru; Ogatta, Sueli Fumie Yamada
We report here for the first time the in vitro effects of (1S,2R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-yl- 39,49,59-trimethoxy benzoate (1) and (1S,2R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-yl benzoate (2) on the growth and ultrastructure of Trypanosoma cruzi. These two synthetic compounds exerted an antiproliferative effect on the epimastigote forms of the parasite. The ICs50/72h of two synthetic L-bornyl benzoates, 1 and 2, was 10.1 and 12.8 mg/ml, respectively. Both compounds were more selective against epimastigotes than HEp-2 cells. Ultrastructural analysis revealed intense cytoplasmic vacuolization and the appearance of cytoplasmic materials surrounded by membranes. The treatment of peritoneal macrophages with compounds 1 and 2 caused a significant decrease in the number of T. cruzi-infected cells. L-Bornyl benzoate derivatives may serve as a potential source for the development of more effective and safer chemotherapeutic agents against T. cruzi infections.
Antinociceptive and edematogenic activity and chemical constituents of Talinum paniculatum Willd.
(2010) Ramos, Maria Perpétua Oliveira; Silva, Grácia Divina de Fátima; Duarte, Lucienir Pains; Peres, Valdir; Miranda, Roqueline Rodrigues Silva de; Souza, Gustavo Henrique Bianco de; Belinelo, Valdenir José; Vieira Filho, Sidney Augusto
Talinum paniculatum (Portulacaceae) is popularly known in the region of Patos de Minas, Minas Gerais State, Brazil, as “Maria Gorda” or “Benção-de-Deus” and in traditional medicine it is used to treat inflammatory processes in general. After dried and fragmented, the plant was sequentially submitted to exhaustive percolation with hexane, ethyl acetate and methanol. The crude extracts were investigated for their anti-edematogenic and anti-nociceptive activities through formalin-induced paw edema model. In comparison with a non-steroidal anti-inflammatory drug (NSAID) indomethacin, the hexane and ethyl acetate extracts showed higher anti-edematogenic and anti-nociceptive activity. In addition, through phytochemical studies, from these extracts were isolated and identified potassium nitrate (1), the mixture of long chain hiodrocarbons hentriacontane (2), dotriacontane (3), tritriacontane (4) and pentatriacontane (5). heneicosanoic acid (6), the ester nonacosyl nonacosanoate (7), urea (8), 3-O-b -Dglucosyl- b -sitosterol (9); the mixture of b -sitosterol (10) and stigmasterol (11), and a pentaciclyc triterpene 3-O-acethyl-aleuritolic acid (12). X-Ray difratometry was used for the characterization of inorganic constituent. TLC, HR-CG and spectrometric methods (IR. 1H and 13C NMR) were used to identify the structures of organic compounds. To the best of our knowledge, it is the first time that compound 1 to 8 and 12 are cited as constituents of T. paniculatum.
Antioxidant activity of Maytenus imbricata Mart., Celastraceae.
(2009) Silva, Grácia Divina de Fátima; Souza, Silvia Ribeiro de; Barbosa, Luiz Cláudio de Almeida; Duarte, Lucienir Pains; Ribeiro, Sônia Machado Rocha; Queiroz, José Humberto de; Vieira Filho, Sidney Augusto; Oliveira, Márcio L. R.
A atividade antioxidante, poder redutor (RP) e a atividade coletora de radicais livres (FRS) usando 2,2-difenil- 1-picrilhidrazil (DPPH), e a concentração de substâncias fenólicas totais dos extratos e substâncias isoladas das folhas, caules e raízes de Maytenus imbricata Mart. (Celastraceae) foram avaliados. Alguns extratos, a mistura de compostos fenólicos e epicatequina mostraram alto poder redutor e atividade antioxidante (DPPH) em comparação com o padrão butilhidroxianisol (BHA) e ácido gálhico (GA) utilizados no ensaio. O extrato acetato de etila das folhas mosraram alto teor de substâncias fenólicas e alto poder redutor e atividade antioxidante em relação aos outros extratos. Este fato indica haver alguma relação entre a concentração de substâncias fenólicas e o poder redutor. O solvente usado no processo de extração influencia a composição química dos extratos e, consequentemente, as atividades redutoras e antioxidantes.
Avaliação da atividade antiulcerogênica da Maytenus truncata Reiss (Celastraceae).
(2005) Silva, R. L; Silva, Renata Pamplona; Martinez, Jorge Rodrigo; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto; Fonseca, Ana Paula Nascentes de Deus; Tagliati, Carlos Alberto
Maytenus truncata Reiss (Celastraceae) e uma planta nativa da Bahia (Brasil), sendo conhecida como “espinheira-santa”. E usada popularmente na forma de decoto das folhas (chas) como antiulcerogênico, similarmente a Maytenus ilicifolia, a verdadeira “espinheira-santa”. O objetivo do presente estudo foi avaliar a atividade antiulcera e cicatrizante, assim como o perfil fotoquímico dos extratos brutos em acetato de etila e metanol da Maytenus truncata. A administração per os desses extratos nas doses de 120 mg/kg e 240 mg/kg reduziu a severidade da lesão gástrica induzida pelo estresse ao frio (-18 °C por 45 minutos) em ratos, com resultados mais significativos para o extrato bruto obtido em metanol. A administração dos extratos provocou o aumento do pH. Os resultados obtidos na administração do extrato bruto em metanol não contrariam seu uso popular, não somente pela atividade observada, mas também por se tratar de um extrato de alta polaridade cujos princípios podem ser obtidos a partir de uma infusão, embora estudos clínicos devam ser realizados para confirmação dessa hipótese.
Chemical constituents from branches of Maytenus gonoclada (Celastraceae) and evaluation of antimicrobial activity.
(2011) Silva, Fernando César; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto; Lula, Ivana Silva; Takahashi, Jacqueline Aparecida; Sallum, William S. T.
Seis triterpenos pentacíclicos isolados dos galhos de Maytenus gonoclada (Celastraceae), incluindo todos os dados de RMN do novo composto 3-oxo-12α,29-diidroxifriedelano são aqui relatados. A estereoquímica do novo friedelano foi estabelecida por dados de RMN bidimensional (HSQC, HMBC e NOESY), e sua massa molecular confirmada por espectrometria de massas (ESI). Testes de atividade antimicrobiana usando método de difusão em disco e de macrodiluição foram realizados contra as bactérias Escherichia coli, Citrobacter freundii e Bacillus cereus, e contra o fungo Candida albicans. O triterpeno 3-oxo-12a-hidroxifriedelano mostrou resultado positivo contra C. albicans.
Chemical constituents of Salacia elliptica (celastraceae).
(2010) Duarte, Lucienir Pains; Figueiredo, Rute Cunha; Sousa, Grasiely Faria de; Soares, Débora Barbosa da Silva; Rodrigues, Salomão Bento Vasconcelos; Silva, Fernando César; Silva, Grácia Divina de Fátima; Vieira Filho, Sidney Augusto
The chemical investigation of Salacia elliptica allowed to the isolation of 20 constituents: two polyols, one xanthone, a mixture of long chain hydrocarbons, one carboxylic acid, one polymer, two steroidal compounds, one aromatic ester and eleven pentacyclic triterpenes. These triterpenes include 3β-stearyloxy-oleanane, 3β-stearyloxy-ursane, one seco-friedelane, and eight compounds of the friedelane serie. The chemical structure and the relative configuration of a new triterpene 1,3-dioxo-16α-hydroxyfriedelane (15) were established through 1H and 13C NMR including 2D experiments (HMBC, HMQC, COSY and NOESY) and herein reported for the first time.
Combined experimental powder x-ray diffraction and DFT data to obtain the lowest energy molecular conformation of friedelin.
(2012) Oliveira, Djalma Menezes de; Mussel, Wagner da Nova; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Duarte, Hélio Anderson; Gomes, Elionai Cassiana de Lima; Guimarães, Luciana; Vieira Filho, Sidney Augusto
Friedelin molecular conformers were obtained by Density Functional Theory (DFT) and by ab initio structure determination from powder X-ray diffraction. Their conformers with the five rings in chair-chair-chair-boat-boat, and with all rings in chair, are energy degenerated in gas-phase according to DFT results. The powder diffraction data reveals that rings A, B and C of friedelin are in chair, and rings D and E in boat-boat, conformation. The high correlation values among powder diffraction data, DFT and reported single-crystal data indicate that the use of conventional X-ray diffractometer can be applied in routine laboratory analysis in the absence of a single-crystal diffractometer.
Complete assignment of the 1H and 13C NMR spectra of a new polyester sesquiterpene from Austroplenckia populnea.
(2000) Vieira Filho, Sidney Augusto; Duarte, Lucienir Pains; Santos, Marcelo Henrique dos; Silva, Grácia Divina de Fátima; Lula, Ivana Silva; Afonso, Robson José de Cássia Franco
new polyester sesquiterpene (4-hydroxy-1,2,6,15-tetraacetyl-9-benzoylagarofuran), together with known friedelane triterpenes (friedelin, -friedelinol and 28-hydroxyfriedelin), was isolated from the leaves of Austroplenckia populnea. The structure and relative stereochemistry of the new ester were based on 2D NMR spectroscopic techniques including HMBC, HMQC and NOESY.
Constituents of fruit pulp of Maytenus salicifolia and complete 1D/2D NMR data of 3beta-hydroxy-D-B-friedo-olean-5-ene.
(2010) Valladão, Frederico Nunes; Miranda, Roqueline Rodrigues Silva de; Oliveira, Gabriela Soares de; Silva, Grácia Divina de Fátima; Duarte, Lucienir Pains; Vieira Filho, Sidney Augusto
A mixture of long-chain hydrocarbons constituted by nonacosane (29C, 7.5%), hentriacontane (31C, 48.3%), and tritriacontane (33C, 30.1%), the ester 1 -acetyloxymethylpentacosa-20 -enyl 10-hydroxydecanoate (2), -amyrin (3), friedelin (4), and lupeol (5), and 3 -hydroxy-D:B-friedo-olean-5-ene (6) were identified as constituents of fruits of Maytenus salicifolia Reissek (Celastraceae). The structural formula and the stereochemistry of compound 6 were established by the data obtained through 1H and 13C NMR spectroscopy, including DEPT-135 and 2D (HMQC, HMBC, and NOESY) experiments. By analysis of the spectral data, it was possible to correct seven chemical shift assignments of compound 6, which were erroneous attributed and published in the scientific literature.
Constituintes químicos e atividade antiespermatogênica em folhas de Austroplenckia populnea (Celastraceae).
(2002) Vieira Filho, Sidney Augusto; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Mazaro, Renata; Stasi, Luiz Cláudio Di
Folhas de Austroplenckia populnea (mangabarana, marmelinho do campo) foram submetidas a estudo fitoquímico. Do extrato hexânico foram isolados e identificados três triterpenos pentacíclicos e um sesquiterpeno agarofurânico inédito. Realizou-se testes de atividade antiespermatogência utilizando parte deste extrato. Os resultados mostraram uma redução significativa do número de espermatozoides no epidídimo.
Constituintes químicos e efeito ecotoxicológico do óleo volátil de folhas de Eucalyptus urograndis (Mirtaceae).
(2010) Araújo, Fabíola Oliveira Lino de; Rietzler, Arnola Cecília; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Carazza, Fernando; Vieira Filho, Sidney Augusto
The volatile oil from the leaves of E. urograndis was analyzed by GC and GC-MS. It was identified 10 compounds in which, orto-cimene (41.4%) and 1,8-cineol (25.8%) were the main constituents. The induction of deleterious effect to aquatic organisms due to the presence of volatile oil lixiviated from E. urograndis leaves was studied using Daphnia laevis and D. similis as bioindicators. Through the results of toxicological tests it was possible to show that the litterbag of E. urograndis represents a risk factor for the aquatic ecosystem of lakes and rivers that are in the surrounding area of large scale Eucalyptus plantations. The method can be used for monitor the quality of these types of aquatic environments.
Cytotoxicity, anti-poliovirus activity and in silico biological evaluation of constituents from Maytenus gonoclada (Celastraceae).
(2014) Oliveira, Mauro Lúcio Gonçalves de; Assenço, Regina Aparecida Gomes; Silva, Grácia Divina de Fátima; Lopes, Júlio César Dias; Silva, Fernando César; Lanna, Maria Célia da Silva; Magalhães, José Carlos de; Duarte, Lucienir Pains; Vieira Filho, Sidney Augusto
Objective: The in silico free access web tools PASS online and ChemMapper were used to predict potential biological activities of compounds 1 to 8 isolated from Maytenus gonoclada (Celastraceae). The constituents 4’-O-methylepigalocatequin (6), tingenone (7) and proanthocyanidin A (8), and ethanolic extracts were subjected to in vitro cytotoxicity using VERO cells and anti-Poliovirus assays. Methods: QSAR and molecular superposition, correlating the average number of pharmacophores were used in the prediction studies. Cellular line VERO ATCC CCL-81 was used to determine anti-Poliovirus effect, observed by colorimetric (MTT) method. The annexing V/propidium iodide assay was used to determine the occurrence of apoptosis in the cytotoxicity assays. Results: The experimental results found for constituents 6-8 were in accordance with observed data obtained through PASS online and ChemMapper simulation. Conclusion: Compound 7 showed higher cytotoxic and apoptosis induction properties, and 6 and 8 presented anti-Poliovirus activity.
Effect of constituents from samaras of Austroplenckia populnea (Celastraceae) on human cancer cells.
(2014) Caneschi, Carolina Milagres; Muniyappa, Mohan Kumar; Duarte, Lucienir Pains; Silva, Grácia Divina de Fátima; Santos, Orlando David Henrique dos; Spillane, Charles; Vieira Filho, Sidney Augusto
Background: Aiming the continuity of the studies of Austroplenckia populnea, Brazilian species of the Celastraceae family, in the present study, it was investigated the effect of crude extracts obtained with ethanol, ethyl acetate and chloroform and two purified constituents, proanthocyanidin A and 4’-O-methylepigallocatechin, both isolated from its samaras, on cancer cell proliferation assays. Materials and Methods: The human cancer cells lines MCF-7 (ductal breast carcinoma), A549 (lung cancer), HS578T (ductal breast carcinoma) and non-cancer HEK293 (embryonic kidney cells) were treated with different concentrations of extracts and constituents and the effect was observed through the acid phosphatase method. The chemical structures of the purified compounds were identified by the respective IR and 1H and 13C nuclear magnetic resonance spectral data. Results: While crude extracts from samaras of the folk medicine A. populnea can trigger cell proliferative effects in human cell lines, the purified compounds (proanthocyanidin A and 4’-O-methyl-epigallocatechin) isolated from the same extracts can have an opposite (anti-proliferative) effect. Conclusion: Based on the results, it was possible to suggest that extracts from samaras of A. populnea should be further investigated for possible cancer-promoting activities; and the active extracts can also represent a source of compounds that have anti-cancer properties.
Epikatonic acid from Austroplenckia populnea : structure elucidation by nmr spectroscopy and x-ray crystallography.
(2002) Silva, Grácia Divina de Fátima; Duarte, Lucienir Pains; Viera Filho, Sidney Augusto; Doriguetto, Antônio Carlos; Mascarenhas, Yvone Primerano
From the chloroform extract of Austroplenckia populnea, epikatonic acid, friedelin, populnonic acid, abruslactone A, salaspermic acid and 22b-epi-maytenfolic acid were isolated. The structure and stereochemistry of epikatonic acid were established by two-dimensional NMR spectroscopic techniques (HMQC, HMBC and NOESY) and later confirmed by single crystal X-ray diffraction as 3b-hydroxyolean- 12-en-29-oic acid, which unambiguously established the configuration of the hydroxyl group at C-3 as 3b-OH and the carboxyl group at C-20 as 20a-COOH. The crystal structure shows two independent molecules in the asymmetric unit. The crystal packing is stabilized by four O–H· · ·O intermolecular hydrogen bonds, which give rise to infinite double chains along the c axis.
Estudo fitoquímico do decocto das folhas de maytenus truncata reissek e avaliação das atividades antinociceptiva, antiedematogênica e antiulcerogênica de extratos do decocto.
(2007) Fonseca, Ana Paula Nascentes de Deus; Silva, Grácia Divina de Fátima; Carvalho, Juliana de Jesus; Meléndez Salazar, Gloria Del Carmen; Duarte, Lucienir Pains; Silva, Renata Pamplona; Jorge, Rodrigo Martinez; Tagliati, Carlos Alberto; Zani, Carlos Leomar; Alves, Tânia Maria de Almeida; Peres, Valdir; Vieira Filho, Sidney Augusto
The present paper describes the phytochemical investigation and biological activities of the chloroform, ethyl acetate and methanol extracts of leaf decocts of M. truncata Reiss (Celastraceae). Our studies afforded two flavonoid glycosides, quercetin-3-Orhamnopyranosyl- O-glucopyranosyl-O-rhamnopyranosyl-O-galactopyranoside (1) and kampferol-3-O-rhamnopyranosyl-Oglucopyranosyl- O-rhamnopyranosyl-O-galactopyranoside (2) from the methanolic extract and dulcitol (3) from the ethyl acetate extract. Ethyl acetate and methanol extracts exhibited considerable antiulcerogenic and analgesic activities. The results of the phytochemical studies suggest that the healing activity of methanol extracts can be related to the presence of glycosyl flavonoids.