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Molecules 2013, 18(5), 5517-5530; doi:10.3390/molecules18055517
Article

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

1, 1, 2, 3, 4, 4, 4 and 1,*
1 Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso, Chile 2 Facultad de Química, Pontificia Universidad Católica de Chile, Vicuña Mackenna N° 4860, Santiago, Chile 3 Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, Chile 4 Centro de Investigaciones Biomédicas, Escuela de Medicina, Universidad de Valparaíso, Av. Hontaneda N° 2664, Valparaíso, Chile
* Author to whom correspondence should be addressed.
Received: 9 April 2013 / Revised: 4 May 2013 / Accepted: 6 May 2013 / Published: 13 May 2013
(This article belongs to the Section Medicinal Chemistry)
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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.
Keywords: sesquiterpenequinone; ent-cyclozonarone; cancer cells; cytotoxicity; apoptosis; caspase 3; mitochondrial membrane permeability sesquiterpenequinone; ent-cyclozonarone; cancer cells; cytotoxicity; apoptosis; caspase 3; mitochondrial membrane permeability
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Sobarzo, N.Q.; Venegas, I.M.; Sánchez, C.S.; Catalán, L.E.; Rojas, C.C.; Valdivia, V.U.; García, J.V.; Fritis, M.C. Synthesis of a New ent-Cyclozonarone Angular Analog, and Comparison of Its Cytotoxicity and Apoptotic Effects with ent-Cyclozonarone. Molecules 2013, 18, 5517-5530.

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