Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives

LANG, K.; SILVA, I.; ZIMMERMANN, L.; ROCHA MACHADO, V.; TEIXEIRA, M.; LAPUH, M. I.; GALETTI, M.A.; PALERMO, J; CABRERA, G.; CAMPOS BERNARDES, L.; SIMOES, C.; SCHENKEL, E.P.; CARO, M.; DURÁN, F.

BIOORGANIC & MEDICINAL CHEMISTRY.

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2012 vol. 20 p. 3016 - 3030

0968-0896

Two cucrbitacins: dihydrocucurbitacin B (1) and cucurbitacin B (2), which can be obtained in large amounts from the roots of Wilbrandia ebracteata and from the fruits of Luffa opperculata, respectively, were used as starting materials for the preparation of a library of twenty-nine semi-synthetic derivatives. The structural changes that were performed include the removal, modification or permutation of functional groups in rings A and B as well as in the side chain. All new semisynthetic compounds, as well as 1 and 2, were tested in vitro for their cytotoxic effects on non-small-cell lung cancer cells (A549 cells). Some of these compound displayed potent to moderate activity against A549 tumor cells, especially those cucurbitacin B derivatives which were modified at ring A.