The extraction of Latrunculia sponges collected along the coast of the Aleutian Islands of Alaska yielded a lipid fraction, in which a natural long-chain monounsaturated aldehyde, (Z)-docos-15-enal (1), was isolated for the first time from this genus of sponge. Experimental, DP4+/DFT structure-probability calculations, and ab initio NMR chemical shift (CS) computational data comparing (Z)-docos-15-enal isolated from a natural sponge source with the previously reported synthetic material, confirmed the cis (Z) configuration of the double bond. Online ozonolysis LC-ESI-MS (OzESI) data validated the assignment of the C-15/C-16 olefin along the lipid chain. Aldehyde-based metabolites may serve as biosynthetic precursors for complex lipid alkaloids such as the atkamine pyrroloiminoquinone (PIQ).
Benjamin et al. (Wed,) studied this question.