Secondary metabolites of the cyanobacterium Microcoleus lyngbyaceus and the sea hare Stylocheilus longicauda: palatability and toxicity

Abstract

The cyanobacterium Microcoleus lyngbyaceus (Kutz.) Crouan (Lyngbya majuscula Gomont) produces a variety of nitrogen-containing secondary metabolites. M. lyngbyaceus is eaten by the specialist sea hare Stylocheilus longicauda, which sequesters secondary metabolites from its diet and transforms some sequestered metabolites into related compounds. We examined the palatability and toxicity of the metabolites malyngamide A, malyngamide B, and a mixture of majusculamides A and B (from M. lyngbyaceus), and malyngamide B acetate (from S. longicauda, derived from malyngamide B), in order to explore a series of hypotheses about why M. lyngbyaceus produces secondary metabolites and why S. longicauda sequesters and transforms them. All three M. lyngbyaceus metabolites significantly reduced feeding by omnivorous pufferfish (Canthigaster solandri) and crabs (Leptodius spp.). Direct comparisons indicated that neither malyngamide A nor the majusculamide mixture differed significantly in palatability from malyngamide B. The S. longicauda metabolite malyngamide B acetate did not significantly deter feeding by either consumer. Direct comparisons indicated that pufferfish found malyngamide B acetate more palatable than malyngamide B, and that crabs showed a non-significant trend in this direction. Palatability of the metabolites did not correlate with toxicity. Although no significant differences were observed among the M. lyngbyaceus metabolites in their palatability, two toxicity assays consistently ranked malyngamide A more toxic than malyngamide B, which was more toxic than the majusculamide mixture. The majusculamide mixture did not significantly differ in toxicity from malyngamide B acetate, even though the two differed strongly in palatability.