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

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• 作者：Karen Luise Lang^a ; ^{karenluise@gmail.com} ; Izabella Thaí ; s Silva^b ; Lara Almida Zimmermann^b ; Vanessa Rocha Machado^b ; Marina Rodrigues Teixeira^b ; Marí ; a Ivana Lapuh^c ; Mariana Alejandra Galetti^c ; Jorge Alejandro Palermo^c ; Gabriela Myriam Cabrera^c ; Lí ; lian Sibelle Campos Bernardes^b ; Clá ; udia Maria Oliveira Simõ ; es^b ; Eloir Paulo Schenkel^b ; Miguel Soriano Balparda Caro^a ; Fernando Javier Durá ; n^c
• 关键词：Cucurbitacins ; Triterpenoids ; Semisynthesis ; Cytotoxic activity
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2012
• 期刊代码：9_09680896
• 类别：ch
• 出版时间：1 May, 2012
• 卷：20
• 期：9
• 页码：3016-3030
• 文件大小：755 K

摘要

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.