Structural studies and antifungal activity of unique polyene amides, clathrynamide A and three new derivatives, from a marine sponge, Psammoclemma sp.

Abstract

Known polyene amide, clathrynamide A, and three novel related metabolites, debromoclathrynamide A, (4E,6E)-debromoclathrynamide A and (6E)-clathrynamide A, were isolated from an Okinawan marine sponge, Psammoclemma sp. The absolute stereochemistry of clathrynamide A was determined to be 3R,12R by the modified Mosher method. The structures of the three new compounds were elucidated by spectroscopic analyses as debromo derivatives and geometrical isomers. Their antifungal activities were also evaluated with a phytopathogenic fungus, indicating that both the bromine atom and double-bond geometry affected the activity.