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Cytotoxic Activity of Semi-Synthetic Derivatives of Elatol and Isoobtusol
Department of Pharmaceutical Sciences, Federal University of Santa Catarina, Florianópolis, SC, 88040-970, Brazil
Department of Organic Chemistry, University of Buenos Aires, Buenos Aires, C1428EGA, Argentina
* Author to whom correspondence should be addressed.
Received: 1 August 2012; in revised form: 12 September 2012 / Accepted: 1 October 2012 / Published: 18 October 2012
Abstract: In the present study, the in vitro cytotoxic effects of six semi-synthetic derivatives of elatol (1) and isoobtusol (2) were investigated. Chemical modifications were performed on the hydroxyl groups aiming to get derivatives of different polarity, namely the hemisuccinate, carbamate and sulfamate. The structural elucidation of the new derivatives was based on detailed NMR and MS spectroscopic analyses. The in vitro cytotoxicity of compounds 1 to 8 was evaluated against A459 and RD tumor cell lines with CC50 values ranging from 4.93 to 41.53 µM. These results suggest that the structural modifications performed on both compounds could be considered a good strategy to obtain more active derivatives.
Keywords: elatol; isoobtusol; sesquiterpenes; synthesis; cytotoxic activity
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Lang, K.L.; Silva, I.T.; Zimmermann, L.A.; Lhullier, C.; Mañalich Arana, M.V.; Palermo, J.A.; Falkenberg, M.; Simões, C.M.O.; Schenkel, E.P.; Durán, F.J. Cytotoxic Activity of Semi-Synthetic Derivatives of Elatol and Isoobtusol. Mar. Drugs 2012, 10, 2254-2264.
Lang KL, Silva IT, Zimmermann LA, Lhullier C, Mañalich Arana MV, Palermo JA, Falkenberg M, Simões CMO, Schenkel EP, Durán FJ. Cytotoxic Activity of Semi-Synthetic Derivatives of Elatol and Isoobtusol. Marine Drugs. 2012; 10(10):2254-2264.
Lang, Karen L.; Silva, Izabella T.; Zimmermann, Lara A.; Lhullier, Cíntia; Mañalich Arana, Maria V.; Palermo, Jorge A.; Falkenberg, Miriam; Simões, Cláudia M. O.; Schenkel, Eloir P.; Durán, Fernando J. 2012. "Cytotoxic Activity of Semi-Synthetic Derivatives of Elatol and Isoobtusol." Mar. Drugs 10, no. 10: 2254-2264.