Simplexolides A-E and plakorfuran A, six butyrate derived polyketides from the marine sponge Plakortis simplex.

Six new polyketides, simplexolides A-E (1-5) and a furan ester, plakorfuran A (6), together with four known furanylidenic methyl esters (7-10) were isolated from the marine sponge Plakortis simplex. Compounds 1-5 feature a tetrahydrofuran ring opened seco-plakortone skeleton. These new structures, including relative configurations, were determined on the basis of extensive analysis of spectroscopic data. The absolute configurations of 1-6 were established by the modified Mosher's method, and the CD exciton chirality method. However, configurations of the remote stereocenters at C-8 in compounds 1-5 were not determined. Antifungal, cytotoxicity, antileismanial, and antimalarial activities of these poly-ketides were evaluated.