The alpha-hydroxy fatty acids 2-hydroxy-eicosanoic (1) acid, 2-hydroxyheneicosanoic (2) acid, 2-hydroxydocosanoic (3) acid, 2-hydroxytetracosanoic (4) acid, 2-hydroxy-23-methyl-tetracosanoic acid and 2-hydroxypentacosanoic (5) acid were isolated from the Caribbean sponges Verongula gigantea and Aplysina archeri. The very long chain fatty acids 5,9-nonacosadienoic acid (29:2) and 5,9,23-tricontatrienoic acid (30:3) were also identified together with the iso-prenoid fatty acid 3,7,11,15-tetramethylhexadecanoic (phytanic) acid that seems to be common in the Aplysinidae. A. archeri contained an extremely long chain fatty acid tentatively characterized as dotricontaenoic (32:1) acid. These acids were found to occur in phosphatidylserine, phosphatidylinositol, phosphatidylethanolamine, phosphatidylcholine and traces of phosphatidylglycerol.
The novel fatty acids 18-methyl-5,9-icosadienoic acid [1] and 19-methyl-5,9-icosadienoic acid [2] were identified in the Caribbean sponge Erylus formosus. Other interesting fatty acids identified were the branched acids 3-methylpentadecanoic acid and 3-methylhexadecanoic acid, which are known to possess larvicidal activity. The most stable conformation of the new acid 19-methyl-5,9-icosadienoic acid is also presented as predicted by Molecular Mechanics (MM2) calculations. The sterol composition of E. formosus is also reported.
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