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Synthesis of a New ent-Cyclozonarone Angular Analog, and Comparison of Its Cytotoxicity and Apoptotic Effects with ent-Cyclozonarone

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Author(s): Natalia Quiñones Sobarzo | Iván Montenegro Venegas | Cristian Salas Sánchez | Luis Espinoza Catalán | Cristóbal Carrasco Rojas | Valentina Ulloa Valdivia | Joan Villena García | Mauricio Cuellar Fritis

Journal: Molecules
ISSN 1420-3049

Volume: 18;
Issue: 5;
Start page: 5517;
Date: 2013;
Original page

Keywords: sesquiterpenequinone | ent-cyclozonarone | cancer cells | cytotoxicity | apoptosis | caspase 3 | mitochondrial membrane permeability

ABSTRACT
The synthesis of a newangular analog 11 of cyclozonarone was achieved via Diels-Alder reaction between a sesquiterpene-1,3-diene and 1,4-benzoquinone. The cytotoxic activity of ent-cyclozonarone [(+)-10] and the angular (−)-cyclozonarone analog 11 has been determined in three human cancer cell lines and in normal fibroblasts using the sulforhodamine B assay. The analyzed isomers induce cell death in different cancer cell lines by eliciting nuclear condensation and fragmentation, decreasing mitochondrial membrane permeability and increasing caspase-3 activity, all traits indicating apoptosis, with the effects of (+)-10 being stronger than those of 11 in all cases.
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