Imines and lactones derived from friedelanes and their cytotoxic activity.
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Date
2018
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Abstract
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.
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Keywords
Pentacyclic triterpenes, Friedelane derivatives, Cytotoxicity property, THP-1 cell line, K562 cell line
Citation
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.