Synthesis of racemic 9-methyl-10-hexadecenoic acid.

The marine bacterial fatty acid 9-methyl-10-hexadecenoic acid was conveniently prepared in 6 steps and in a 22% overall yield, starting from commercially available methyl 10-hydroxydecanoate. The naturally occurring fatty acid has the E double bond configuration as confirmed by gas chromatographic co-elution experiments.

Fatty acid composition of bacteria associated with the toxic dinoflagellate Ostreopsis lenticularis and with Caribbean Palythoa species.

The fatty acid composition of a Pseudomonas sp. (Alteromonas) and its host, the dinoflagellate Ostreopsis lenticularis, vectors in ciguatera fish poisoning, has been studied. The major fatty acids in O. lenticularis were 16:0, 20:5n-3, and 22:6n-3, but 18:2n-6, 18:3n-3, and 18:n-3 were also identified. In contrast to other dinoflagellates, 1 8:5n-3 was not detected in O. lenticularis. Even-chain fatty acids such as 9-16:1, 11-18:1, and 13-20:1 predominated in the Pseudomonas sp. from O. lenticularis, but 1 6-20% of (E)-11-methyl-12-octadecenoic acid was also identified. The chirality of the latter was confirmed by total synthesis (28% overall yield) starting from oxacyclotridecan-2-one. The fatty acid compositions of two other Pseudomonas species, from the palytoxin-producing zoanthids Palythoa mamillosa and P. caribdea, were also studied and were similar to that of the Pseudomonas sp. from O. lenticularis. The possibility of using some of these fatty acids as chemotaxonomic lipids in identifying marine animals that consume toxic dinoflagellates or zoanthids is discussed.