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

  • Bioorg Med Chem. 2012 May 1;20(9):3016-30. doi: 10.1016/j.bmc.2012.03.001.
Karen Luise Lang  1 ,  Izabella Thaís Silva ,  Lara Almida Zimmermann ,  Vanessa Rocha Machado ,  Marina Rodrigues Teixeira ,  María Ivana Lapuh ,  Mariana Alejandra Galetti ,  Jorge Alejandro Palermo ,  Gabriela Myriam Cabrera ,  Lílian Sibelle Campos Bernardes ,  Cláudia Maria Oliveira Simões ,  Eloir Paulo Schenkel ,  Miguel Soriano Balparda Caro ,  Fernando Javier Durán
Affiliations
  • 1. Programa de Pós-Graduação em Química, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil. [email protected]
PMID: 22472043 DOI: 10.1016/j.bmc.2012.03.001
Abstract

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.