Aplysia sea hare assimilation of secondary metabolites from brown seaweed,Stypopodium zonale.

JuvenileAplysia dactylomela were found feeding in abundance on the tropical brown algaStypopodium zonale, a seaweed previously shown to contain numerous unique terpene-quinone natural products. Lipid extracts of these herbivorous mollusks were shown by TLC and HPLC-NMR analyses to contain appreciable quantities of twoS. zonale metabolites as well as one new but closely related compound. Spectroscopic analyses of the new compound in concert with functional group modifications identified this new compound as 3-keto epitaondiol. A careful analysis of the seaweed extract failed to locate this ketone, and thus, it most likely represents anAplysia-biotransformed compound. This is the first clear reported observation of metabolite transfer between an alga of the phylum Phaeophyta and a sea hare.