Polycyclic guanidine alkaloids from the marine sponge Crambe crambe and Ca++ channel blocker activity of crambescidin 816.

Four pentacyclic guanidine derivatives (crambescidin 800 [5], crambescidin 816 [6], isocrambescidin 800 [9], and crambine [10]) related to ptilomycalin A [11] have been isolated from the Mediterranean sponge Crambe crambe. Isocrambescidin 800 and crambidine are new derivatives, the structures of which have been determined on the basis of their spectral properties. The absolute configuration of crambescidin 816 at the stereogenic center C-43 has been determined by applying Mosher's method. Pharmacological and biological activities of the Crambe crambe alkaloids are reported. In particular, crambescidin 816 was found to have a potent Ca++ antagonist effect and to inhibit the acetylcholine-induced contraction of guinea pig ileum at very low concentrations.