Marine-derived biologically active natural products continue to be a source of potential therapeutic compounds. An unusual group of fatty acids (FA), such as the 5,9-diunsaturated and the 2-methoxylated FA have been identified from marine invertebrates and some of them are known to arise a from symbiotic relationship between bacteria with the host cells. These FA have shown a variety of biological properties. We studied the effect of 2-methoxylated FA on human neuroblastoma SH-SY5Y cells, showing that cultures treated with the 2-methoxylated FA for 48h were cytotoxic in comparison to cell cultures treated with the corresponding non-methoxylated FA. Recently, we identified in the Caribbean sponge Erylus goffrilleri, the novel (5Z,9Z)-2-methoxy-5,9-eicosadienoic acid. In order to further scrutinize the analytical and biological properties of this acid we developed a total synthesis in 9 steps and 8% overall yield. The total synthesis of the acid as well as the spectral and biological data obtained will be presented.

Total synthesis of (5Z,9Z)-2-methoxy-5,9-eicosadienoic acid, identified in the Caribbean sponge Erylus goffrilleri, as a cytotoxic compound against human neuroblastoma SH-SY5Y cells

245th National Meeting (2013)

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