title: Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives.
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.
authors.affiliation: Programa de Pós-Graduação em Química, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil. karenluise@gmail.com
authors.forename: Karen Luise
authors.initials: KL
authors.lastname: Lang
authors.forename: Izabella Thaís
authors.initials: IT
authors.lastname: Silva
authors.forename: Lara Almida
authors.initials: LA
authors.lastname: Zimmermann
authors.forename: Vanessa Rocha
authors.initials: VR
authors.lastname: Machado
authors.forename: Marina Rodrigues
authors.initials: MR
authors.lastname: Teixeira
authors.forename: María Ivana
authors.initials: MI
authors.lastname: Lapuh
authors.forename: Mariana Alejandra
authors.initials: MA
authors.lastname: Galetti
authors.forename: Jorge Alejandro
authors.initials: JA
authors.lastname: Palermo
authors.forename: Gabriela Myriam
authors.initials: GM
authors.lastname: Cabrera
authors.forename: Lílian Sibelle Campos
authors.initials: LS
authors.lastname: Bernardes
authors.forename: Cláudia Maria Oliveira
authors.initials: CM
authors.lastname: Simões
authors.forename: Eloir Paulo
authors.initials: EP
authors.lastname: Schenkel
authors.forename: Miguel Soriano Balparda
authors.initials: MS
authors.lastname: Caro
authors.forename: Fernando Javier
authors.initials: FJ
authors.lastname: Durán
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D019662:Cucurbitaceae / Q000737:chemistry; D005638:Fruit / Q000737:chemistry; D006801:Humans; D029776:Luffa / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*
chemical_list: D000970:Antineoplastic Agents; D014315:Triterpenes; C523469:dihydrocucurbitacin B; C041246:cucurbitacin B