DEFAR - Departamento de Farmácia

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Browsing DEFAR - Departamento de Farmácia by Author "Aguilar, Mariana Guerra de"

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    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.
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    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 Pains
    Friedelan-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.