Amphidinolide P from the Brazilian octocoral Stragulum bicolor

Chemical analysis of the octocoral Stragulum bicolor and its prey the nudibranch Marionia limceana revealed higher concentrations of amphidinolide P (1) and the related methyl derivative 2. Amphidinolides have been so far reported only from laboratory cultures of the dinoflagellate Amphidinium sp., thus this is the first identification of this class of polyketides in marine invertebrates. Dinoflagellates are an important source of unique bioactive secondary metabolites. Symbiotic species, commonly named zooxanthellae, transfer most of their photosynthetically fixed carbon to their host. The mutualistic relationship provides the organic metabolites used for energy production but there are very few reports of the role of the dinoflagellates in the production of secondary metabolites in the symbiotic association. Corals and other related cnidarians are the most well-known animals containing symbiotic dinoflagellates. In the present paper we describe the isolation of amphidinolide P (1) from the octocoral Stragulum bicolor and its prey, the nudibranch Marionia limceana, collected off the coasts of Fortaleza (Ceará, Brazil). The coral extracts also contained 3-O-methyl derivative (2) of amphidinolide P, together with minor compounds still under investigation. Amphidinolides have been so far reported only in laboratory cultures of Amphidinium sp., thus compounds 1 and 2 represents the first identification of these polyketides in invertebrates. The finding proves the possibility to isolate amphidinolides from a natural symbiosis, enabling further biological and biotechnological studies.