Coriacenins, a New Class of Long Alkyl-Chain Amino Alcohols from the Mediterranean Sponge Clathrina coriacea

The Mediterranean sponge Clathrina coriacea contains a series of long chain amino alcohols, named coriacenins (2-6), belonging to a new class of alkaloids. The structures of the novel compounds were elucidated by studying, with a combination of spectral and chemical methods, their peracetyl derivatives (2a-6a). Coriacenins are characterized by a bis(1,3-diamino-2-propanol) moiety and a linear alkyl chain varying both by length and by degree of unsaturation. The biosynthetic pathway leading to coriacenins seems to be unprecedented. It should, however, occur through condensation of an acetogenin with an uncommon amino acid.