Cytotoxic oxasqualenoids from the red alga Laurencia viridis.

Francisco Cen-Pacheco, Janny A Villa-Pulgarin, Faustino Mollinedo, Manuel Norte, Antonio H Daranas, José J Fernández

Instituto Universitario de Bio-Orgánica Antonio González, Universidad de la Laguna, Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.

European journal of medicinal chemistry 2011 Aug

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Three new polyether squalene derivatives 15-dehydroxythyrsenol A (2), prethyrsenol A (3) and 13-hydroxyprethyrsenol A (4) have been isolated from the red alga Laurencia viridis. Their structures were determined through the interpretation of NMR spectroscopic data and chemical correlations. In addition, four semi-synthetic compounds modulating the solubility of the lead compound dehydrothyrsiferol (1) were prepared without loss of activity. The cytotoxicity of the new compounds exhibited low μM activities. In order to explain their biological properties, docking simulations of the natural and synthetic compounds onto the αvβ3 integrin binding region were carried out. Copyright © 2011 Elsevier Masson SAS. All rights reserved.

Citation

Francisco Cen-Pacheco, Janny A Villa-Pulgarin, Faustino Mollinedo, Manuel Norte, Antonio H Daranas, José J Fernández. Cytotoxic oxasqualenoids from the red alga Laurencia viridis. European journal of medicinal chemistry. 2011 Aug;46(8):3302-8