Structure and cytotoxicity of new metabolites from the sponge Mycale cecilia

Tetrahedron
2004.0

Abstract

The chemical study of the sponge Mycale cecilia has led to the isolation of 14 new pyrrole-containing metabolites. Mycalazals 3–13 are pyrrole-2-carbaldehydes possessing at C-5 hydrocarbon side chains of different length and/or number of unsaturations. Mycalenitriles 1–3 are 5-cyanoalkylpyrrole-2-carbaldehydes. The structures of the new compounds were established mainly by NMR and MS spectroscopic analysis. The location of the double bond in mycalazal-4, -8, and -11 was determined by MS analysis of the corresponding bis(methylthio) derivatives. Mycalazals have shown activity as growth inhibitors of several tumor cell lines, in particular the LNcaP cell line, being mycalazal-8 the most active metabolite.

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