Ecological role for pteroenone,a novel antifeedant from the conspicuous antarctic pteropod Clione antarctica (Gymnosomata: Gastropoda)

Dense populations of the antarctic pteropod Clione antarctica (Smith) offer a rich source of potential nutrients and energy to planktivorous predators. Nonetheless, antarctic fish do not prey on C. antarctica. Employing flash and high-pressure liquid chromatographic techniques, a linear -hydroxyketone, pteroenone (C₁₄H₂₄O₂) was isolated from whole tissues of C. antarctica. When embedded in alginate food pellets at ecologically relevant concentrations, pteroenone caused significant feeding deterrence in Pagothenia borchgrevinki and Pseudotrematomas bernacchii, two antarctic fish known to feed on planktonic organisms. Concentrations of pteroenone were variable between pteropods (0.056 to 4.5 mg ml^-1 tissue), but even those individuals with the lowest natural concentration contained levels five-fold greater than the lowest effective feeding-deterrent concentration (0.012 mg ml^-1 alginate). Chemical analysis indicated that the primary dietary item of the carnivorous C. antarctica, the shelled pteropod Limacina helicina, does not contain pteroenone. This suggests that C. antarctica does not derive this defensive compound from its diet. This is the first example of a defensive secondary metabolite in a pelagic gastropod.