Identification of naturally occurring trans, trans delta 5,9 fatty acids from the sponge Plakortis halichondroides

The first trans fatty acids from a Sponge have been isolated from Plakortis halichondroides. The Sponge was shown to contain the iso acids (5E,9E)-19-methyl-5,9-eicosadienoic, (5E,9E)-20-methyl-5,9-heneicosadienoic and (5E,9E)-21-methyl-5,9-docosadienoic acid, as well as the anteiso acids (5E,9E)-19-methyl-5,9-heneicosadienoic and (5E,9E)-20-methyl-5,9-docosadienoic acid together with the straight chain (5E,9E)-5,9-docosadienoic acid. The acids were shown by gas chromatography, Fourier transform infrared and 13C nuclear magnetic resonance to contain the trans configuration. An eicosadienoic acid, namely (6E,14E)-6,14-eicosadienoic acid, and 12-methyl-5-octadecenoic acid were also identified in a Sponge for the first time. The fatty acids were shown to be the principal constituents of phosphatidylethanolamine and phosphatidylcholine. No sterols were found in the Sponge. The results presented in this work should be helpful in taxonomy of Homoscleromorpha.