Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives
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...
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todo:paper_09680896_v20_n9_p3016_Lang2023-10-03T15:55:16Z Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives Lang, K.L. Silva, I.T. Zimmermann, L.A. MacHado, V.R. Teixeira, M.R. Lapuh, M.I. Galetti, M.A. Palermo, J.A. Cabrera, G.M. Bernardes, L.S.C. Simões, C.M.O. Schenkel, E.P. Caro, M.S.B. Durán, F.J. Cucurbitacins Cytotoxic activity Semisynthesis Triterpenoids 16 oxo dihydrocucurbitacin b 2 bromo dihydrocucurbitacin b 2 deoxy dihydrocucurbitacin b 2,16 dideoxy dihydrocucurbitacin b cucurbitacin cucurbitacin b derivative dihydrocucurbitacin b Luffa operculata extract plant extract unclassified drug Wilbrandia ebracteata extract article cell viability chemical modification chemical reaction concentration response controlled study Cucurbitaceae drug cytotoxicity drug screening drug specificity drug structure drug synthesis fruit human human cell IC 50 in vitro study luffa operculata lung non small cell cancer plant root structure activity relation structure analysis Wilbrandia ebracteata Antineoplastic Agents Cell Line, Tumor Cell Proliferation Cucurbitaceae Fruit Humans Luffa Plant Roots Triterpenes Luffa operculata Wilbrandia ebracteata 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. © 2012 Elsevier Ltd. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09680896_v20_n9_p3016_Lang |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Cucurbitacins Cytotoxic activity Semisynthesis Triterpenoids 16 oxo dihydrocucurbitacin b 2 bromo dihydrocucurbitacin b 2 deoxy dihydrocucurbitacin b 2,16 dideoxy dihydrocucurbitacin b cucurbitacin cucurbitacin b derivative dihydrocucurbitacin b Luffa operculata extract plant extract unclassified drug Wilbrandia ebracteata extract article cell viability chemical modification chemical reaction concentration response controlled study Cucurbitaceae drug cytotoxicity drug screening drug specificity drug structure drug synthesis fruit human human cell IC 50 in vitro study luffa operculata lung non small cell cancer plant root structure activity relation structure analysis Wilbrandia ebracteata Antineoplastic Agents Cell Line, Tumor Cell Proliferation Cucurbitaceae Fruit Humans Luffa Plant Roots Triterpenes Luffa operculata Wilbrandia ebracteata |
| spellingShingle |
Cucurbitacins Cytotoxic activity Semisynthesis Triterpenoids 16 oxo dihydrocucurbitacin b 2 bromo dihydrocucurbitacin b 2 deoxy dihydrocucurbitacin b 2,16 dideoxy dihydrocucurbitacin b cucurbitacin cucurbitacin b derivative dihydrocucurbitacin b Luffa operculata extract plant extract unclassified drug Wilbrandia ebracteata extract article cell viability chemical modification chemical reaction concentration response controlled study Cucurbitaceae drug cytotoxicity drug screening drug specificity drug structure drug synthesis fruit human human cell IC 50 in vitro study luffa operculata lung non small cell cancer plant root structure activity relation structure analysis Wilbrandia ebracteata Antineoplastic Agents Cell Line, Tumor Cell Proliferation Cucurbitaceae Fruit Humans Luffa Plant Roots Triterpenes Luffa operculata Wilbrandia ebracteata Lang, K.L. Silva, I.T. Zimmermann, L.A. MacHado, V.R. Teixeira, M.R. Lapuh, M.I. Galetti, M.A. Palermo, J.A. Cabrera, G.M. Bernardes, L.S.C. Simões, C.M.O. Schenkel, E.P. Caro, M.S.B. Durán, F.J. Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives |
| topic_facet |
Cucurbitacins Cytotoxic activity Semisynthesis Triterpenoids 16 oxo dihydrocucurbitacin b 2 bromo dihydrocucurbitacin b 2 deoxy dihydrocucurbitacin b 2,16 dideoxy dihydrocucurbitacin b cucurbitacin cucurbitacin b derivative dihydrocucurbitacin b Luffa operculata extract plant extract unclassified drug Wilbrandia ebracteata extract article cell viability chemical modification chemical reaction concentration response controlled study Cucurbitaceae drug cytotoxicity drug screening drug specificity drug structure drug synthesis fruit human human cell IC 50 in vitro study luffa operculata lung non small cell cancer plant root structure activity relation structure analysis Wilbrandia ebracteata Antineoplastic Agents Cell Line, Tumor Cell Proliferation Cucurbitaceae Fruit Humans Luffa Plant Roots Triterpenes Luffa operculata Wilbrandia ebracteata |
| description |
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. © 2012 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Lang, K.L. Silva, I.T. Zimmermann, L.A. MacHado, V.R. Teixeira, M.R. Lapuh, M.I. Galetti, M.A. Palermo, J.A. Cabrera, G.M. Bernardes, L.S.C. Simões, C.M.O. Schenkel, E.P. Caro, M.S.B. Durán, F.J. |
| author_facet |
Lang, K.L. Silva, I.T. Zimmermann, L.A. MacHado, V.R. Teixeira, M.R. Lapuh, M.I. Galetti, M.A. Palermo, J.A. Cabrera, G.M. Bernardes, L.S.C. Simões, C.M.O. Schenkel, E.P. Caro, M.S.B. Durán, F.J. |
| author_sort |
Lang, K.L. |
| title |
Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives |
| title_short |
Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives |
| title_full |
Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives |
| title_fullStr |
Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives |
| title_full_unstemmed |
Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives |
| title_sort |
synthesis and cytotoxic activity evaluation of dihydrocucurbitacin b and cucurbitacin b derivatives |
| url |
http://hdl.handle.net/20.500.12110/paper_09680896_v20_n9_p3016_Lang |
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