New delta 5,9 fatty acids in the phospholipids of the sea anemone Stoichactis helianthus.

Abstract

The diunsaturated fatty acids 5,9-heneicosadienoic acid, 5,9-docosadienoic acid and 5,9-tricosadienoic acid, the brominated fatty acids 6-bromo- 5,9-heneicosadienoic acid and 6-bromo-5,9-docosadienoic acid, and the polyunsaturated fatty acids 5,9,13-eicosatrienoic acid and 5,9,13-docosatrienoic acid, were identified for the first time in nature in the phospholipids (mainly phosphatidylethanolamine and phosphatidylserine) of the anemone Stoichactis helianthus. Structural elucidation was accomplished by means of mass spectrometry and chemical transformations such as pyrrolidide and dimethyldisulfide derivatization. Other delta 5,9 fatty acids such as 5,9-hexadecadienoic acid, 5,9-octadecadienoic acid, and 5,9-eicosadienoic acid were also identified in the anemone. Our results indicate that delta 5,9 phospholipid fatty acids are not unique to sponges, as previously recognized, but can be found in other marine invertebrates such as an anemone. 24-Methylated sterols predominated in the sterol composition of the anemone investigated.