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

KAREN L. LANG; IZABELLA T. SILVA; LARA A. ZIMMERMANN; VANESSA ROCHA MACHADO; MARINA RODRIGUES TEIXEIRA; M. IVANA LAPUH; MARIANA A. GALETTI; JORGE A. PALERMO; GABRIELA M. CABRERA; LÍLIAN S. CAMPOS BERNARDES; CLÁUDIA M. OLIVEIRA SIMÕES; ELOIR P. SCHENKEL; MIGUEL S. BALPARDA CARO; FERNANDO J. DURÁN

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

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

0960-894X

Two cucurbitacins, 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 operculata, respectively, were used as starting materials for the preparation of a library of 29 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.