Imines and lactones derived from friedelanes and their cytotoxic activity.

Resumo
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.
Descrição
Palavras-chave
Pentacyclic triterpenes, Friedelane derivatives, Cytotoxicity property, THP-1 cell line, K562 cell line
Citação
AGUILAR, M. G. de. et al. Imines and lactones derived from friedelanes and their cytotoxic activity. Natural Product Research, v. 34, 2018. Disponível em: <https://www.tandfonline.com/doi/full/10.1080/14786419.2018.1508137>. Acesso em: 11 out. 2022.