DEFAR - Departamento de Farmácia
URI permanente desta comunidadehttp://www.hml.repositorio.ufop.br/handle/123456789/530
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Resultados da Pesquisa
Item Imines and lactones derived from friedelanes and their cytotoxic activity.(2018) Aguilar, Mariana Guerra de; Sousa, Grasiely Faria de; Evangelista, Fernanda Cristina Gontijo; Sabino, Adriano de Paula; Vieira Filho, Sidney Augusto; Duarte, Lucienir PainsFriedelan-3-one (1) and friedelane-3,16-dione (2) isolated from leaves and branches of Maytenus robusta Reissek were subjected to structural modifications via nucleophilic addition to the carbonyl group and Baeyer-Villiger oxidation in order to synthesize potential cytotoxic compounds. The oximes friedelane-3-hydroxyimino (3) and 3-hydroxyiminofriedelan-16-one (4) together with the lactones friedelane-3,4-lactone (5) and 3,4-lactonefriedelan-16-one (6) were characterized by IR and NMR spectroscopic analyses. Compounds 4 and 6 are reported for the first time. Cytotoxic screening via MTT assay in human leukemia cell lines (THP-1 and K562) demonstrated no significant improvement of compounds 3-6 when compared to the starting materials. Only compounds 3 and 5 demonstrated an improvement against K562 cells. However, the same assay on ovar- ian and breast cancer cell lines (TOV-21G and MDA-MB-231) showed a reduction in the IC50 for compounds 4-6, indicating that ring A modifications may enhance the biological potential.Item Chemical constituents and allelopathic activity of the essential oil from leaves of Eremanthus erythropappus.(2018) Pinto, Ana Paula Resende; Seibert, Janaína Brandão; Santos, Orlando David Henrique dos; Vieira Filho, Sidney Augusto; Nascimento, Andréa Mendes doThe essential oil from leaves of Eremanthus erythropappus (DC.) MacLeish (Asteraceae) collected in South-eastern Brazil was extracted using a combination of water and steam distillation and investigated by chromatography/mass spectrometry (GC-MS). The sesquiterpene hydrocarbons were predominant (46.6%), followed by oxygenated sesquiterpenes (29.3%) and monoterpene hydrocarbons (18.8%). The major compounds were (β)-caryophyllene (29.3%), caryophyllene oxide (22.1%) and β-pinene (12.8%). The allelopathic activity of E. erythropappus essential oil on the seed germination and radicle length of seedlings was evaluated in lettuce (Lactuca sativa L.), tomato (Lycopersicum esculentum Mill.) and in two field weeds (field mustard – Brassica rapa L. and hairy beggarticks – Bidens pilosa L.). Among the weed species tested, the most significant inhibition of seed germination was observed in field mustard, as measured by the half–minimal inhibitory concentration, IC50 (IC50 = 26.5 μL mL–1), and the most significant inhibitory effect on radicle length of seedlings was observed in seedlings of hairy beggarticks (IC50 = 16.3 μL mL–1). In contrast, the lowest allelopathic effects of E. erythropappus essential oil on seed germination and radicle length of seedlings were observed in tomato (IC50 = >200 μL mL–1 and 130.1 μL mL–1 respectively) and lettuce (IC50 = 97.1 μL mL–1 and 35.1 μL mL–1 respectively). These results revealed significant allelopathic potential of E. erythropappus essential oil against weeds, but minimal effect on lettuce and tomato germination, and thus suggests it is feasible to use E. erythropappus sustainability as an eco-friendly bioherbicide in cropping settings.Item Antibacterial activity of extract and fractions from branches of Protium spruceanum and cytotoxicity on fibroblasts.(2017) Amparo, Tatiane Roquete; Rodrigues, Ivanildes Vasconcelos; Seibert, Janaína Brandão; Souza, Rafaella Hilda Zaniti; Oliveira, Amanda Ribeiro de; Cabral, Vivette Appolinário Rodrigues; Vieira, Paula Melo de Abreu; Brandão, Geraldo Célio; Okuma, Adriana Akemi; Vieira Filho, Sidney Augusto; Teixeira, Luiz Fernando de Medeiros; Souza, Gustavo Henrique Bianco deThe crude ethanol extract (CEE) and fractions from branches of Protium spruceanum were subjected to antibacterial and cytotoxicity assays. Compounds of the most active fraction were identified by GC-MS and LC-MS. CEE was active against 19 bacteria and the ethyl acetate fraction (EAF) showed the lowest minimum bactericidal concentration (MBC 0.3–80.0 mg/mL). Through time-kill assay was observed that EAF induced rapid bactericidal effect against Staphylococcus saprophyticus. The cytotoxicity tests against L929 fibroblasts showed great potential of EAF on the treatment of infections caused by five bacteria (MBC < IC50). The results provide in vitro scientific support to the possible application of branches of P. spruceanum as antimicrobial agent that may contribute for treatment of infections.Item Potencial fitotóxico de Pterodon polygalaeflorus Benth (Leguminosae) sobre Acanthospermum australe (Loefl.) O. Kuntze e Senna occidentalis (L.).(2009) Belinelo, Valdenir José; Vieira Filho, Sidney Augusto; Almeida, Marcelo Suzart de; Alves, Dalton Luiz FerreiraO objetivo dessa pesquisa foi sintetizar e caracterizar a atividade alelopática de derivados do ácido 6α,7β–di-hidroxivouacapan-17β–óico, isolado de sementes de Pterodon polygalaeflorus Benth (Leguminosae). A caracterização dos compostos envolveu espectrometria no infravermelho (IV) e ressonância magnética nuclear de hidrogênio e de carbono (RMN de 1H e de 13C) incluindo experimentos em duas dimensões (COSY 1H 1H, HMQC e HMBC). Os efeitos alelopáticos foram avaliados através de bioensaios de germinação de sementes e crescimento radicular, em condições controladas de temperatura (25 °C) e fotoperíodo (12 h claro/12h escuro), durante 72 horas. Concentrações de 1,0, 100,0 e 1000,0 mg.L-1 foram testadas. Senna occidentalis (fedegoso) e Acanthospermum australe (carrapichinho) foram utilizadas como espécies daninhas alvo. Foi observado que o efeito alelopático dos compostos aumentou em função do aumento da concentração, mostrando assim uma relação dose dependente. A tendência geral observada nos resultados foi de aumento da intensidade dos efeitos alelopáticos inibitórios em função do aumento da concentração. A N-Etil-6α-acetoxi-7β- hidroxivouacapan-17β–amida e N,N-Dietil-6α-acetoxi-7β-hidroxivouacapan-17β–amida foram os derivados que apresentaram maior efeito inibidor da germinação e do crescimento radicular do fedegoso e do carrapichinho. Portanto, esses compostos representam grande potencial aleloquimico contra essas ervas daninha.Item 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 AugustoThe 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.Item Insignificant level of in vitro cytotoxicity, anti‑rotavirus, antibacterial, and antifungal activities of N‑alkylmaleamic acids.(2013) Belinelo, Valdenir José; Campos, Michele Soares Tacchi; Antunes, Rafael Martins; Assenço, Regina Aparecida Gomes; Vieira Filho, Sidney Augusto; Lanna, Maria Célia da Silva; Marçal, Eduardo da Costa; Fonseca, Thaisa Helena Silva; Gomes, Maria Aparecida; Magalhães, José Carlos deBy reacting maleic anhydride with amines, we synthesized the derivatives N‑ethyl, N‑(2‑ethylamine), N‑piperidinyl, N‑phenyl, and N‑phenylhydrazinyl maleamic acids. The purity of these products was initially verified by melting range and the presence of only one spot observed by thin layer chromatography. The chemical structures of the obtained N‑alkyl maleamic acids were confirmed through infrared (IR) and hydrogen and carbon nuclear magnetic resonance (1 H and 13C NMR) spectrometry. Due to the already proven pharmacological activity of maleimides, maleic anhydride and its N‑alkyl maleamic acids were subjected to in vitro assays to observe antiviral (SA‑11 rotavirus), antibacterial (Escherichia coli, Staphylococcus aureus, and Bacillus cereus), antifungal (Colletotrichum musae, Fusarium solani f. sp. phaseoli, Fusarium solani f. sp. piperis Alb., and Penicillium sp.), and antiprotozoal (Trichomonas vaginalis, Giardia lamblia, and Entamoeba histolytica) effects. To study the anti‑rotavirus properties, firstly the 3‑(4,5‑dimethylthiazol‑2‑yl)‑2‑5‑diphenyltetrazolium bromide (MTT) method was used to establish the median cytotoxicity concentration (CC50) of the compounds, using MA‑104 cell line. Under the experimental conditions used, cytotoxic, anti‑rotavirus, antibacterial, and antifungal properties were not observed for these compounds.Item The anti-oxidant properties of isothiocyanates : a review.(2013) Figueiredo, Sônia Maria de; Vieira Filho, Sidney Augusto; Machado, José Augusto Nogueira; Caligiorne, Rachel BasquesCruciferous vegetables, such as broccoli and watercress, have been studied extensively aiming to evaluate their chemopreventive properties. Some of them have already been established using animal models. The ITCs induce Phase II enzymes related to detoxification processes of chemical carcinogens to prevent the start of carcinogenesis. They also exhibit antitumor activity at post-initiation phase, suggesting their additional role(s) in cancer prevention. Sulforaphane is the most extensively studied isothiocyanate, focused in its anti-tumoral activity and it is mainly found in great amounts in broccoli and other cruciferous. In a dose dependent manner, ITCs inhibit the cell viability of human cervical cancer cells, human pancreatic cancer cells, human hepatocellular carcinoma cells, human ovarian cancer cells, and have antiinflammatory properties in the treatment of human T-cell leukemia cells. This protective effect may be due to improved antioxidant status. Although the health effects of diet in humans are generally considered promising, there are definite challenges and limitations of the current data in better understanding of the molecular mechanisms responsible for this effect, together with the possible interactions between different dietary constituents. The survey of relevant patents on the use of isothiocyanates such as sulforaphane for cancer and cardiovascular diseases treatments is also included in this review.Item 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 Franconew 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.Item Antiedematogenic and antinociceptive effects of leaves extracts from Protium spruceanum Benth.(2013) Rodrigues, Ivanildes Vasconcelos; Souza, Juliana Neves de Paula; Silva, Ana Cláudia G.; Chibli, Lucas Apolinário; Cabral, Vivette Appolinário Rodrigues; Vieira Filho, Sidney Augusto; Perazzo, Fábio Ferreira; Guimarães, Andrea Grabe; Souza, Gustavo Henrique Bianco deEthnopharmacological relevance: In traditional medicine, gums and oil-resins from Protium species have been used for many diseases, however, there are no reports of studies of Protium spruceanum’ leaves. Materials and methods: The antiedematogenic and antinociceptive effects of crude ethanol extract (EEB) from leaves of P. spruceanum and its fractions were evaluated in biological models. The fractions were obtained with hexane (FHEX) and methanol (FMEOH). Rat paw edema induced by carrageenan, writhing test, formalin test, hot plate test and the toxicity of EEB were performed. Results: Phytochemical analysis has shown the presence of a and b-amyrins as major constituents of FHEX. Promising results of anti-inflammatory and antinociceptive activity were found for EEB, FHEX and FMEOH. Also were observed the EEB at 6000 mg/kg showed no toxicity. Conclusions: One might suggest that the activities of FHEX are due to the presence of a and b-amyrins and contributes to the biological activities of EEB.Item Physicochemical characteristics of Brazilian green propolis evaluated during a six-year period.(2017) Figueiredo, Sônia Maria de; Binda, Nancy Scardua; Vieira Filho, Sidney Augusto; Almeida, Bruno de Moura; Abreu, Sheila Rago Lemos; Paulino, Niraldo; Pastore, Gláucia Maria; Sato, Hélia Harumi; Theodoropoulos, Viviane Cristina Toreti; Tapia, Eulália Vargas; Park, Yong Kun; Caligiorne, Rachel BasquesBackground: Propolis has been used as a natural health product mainly due to the presence of polyphenols, flavonoids, phenolic aldehydes, amino acids, vitamins and others bioactive constituents. To this natural substance are attributed different biological and pharmacological properties which are influenced by its chemical composition and organoleptic properties. The aim of this work was to evaluate the physicochemical properties and parameters of green propolis collected during a period of six years (2008-2013) in the state of Minas Gerais, located at the southeastern region of Brazil. Methods: The methodology were in accordance with Brazilian legislation on the identity and quality standards of propolis. The evaluated parameters of hydroalcoholic from green propolis were total flavonoids, antioxidant activity - DPPH method, oxidation index, wax content, humidity and insoluble impurities. Results: Propolis samples collected in different seasons during the years 2008 to 2013 presented mean values of total flavonoids (3.4 ± 0.11 mg/g), antioxidant activity DPPH (4.76 ± 0.16 μg/mL), oxidation index (3, 4 ± 0.33 seconds) and wax (15.14 ± 0.78% m/m), which are in accordance with Brazilian legislation. Conclusion: Green propolis did not show abrupt seasonal changes during the six years of investigation, and may be considered as an adequate functional ingredient.