Structure and synthesis of a unique isocyanide serinol-like lipid isolated from the marine mollusk Actinocyclus papillatus

(-)-Actisonitrile, a lipid based on a serinol ether skeleton, was isolated from the opisthobranch mollusk Actinocyclus papillatus. The structure was established by spectroscopic methods whereas the absolute configuration of the chiral centre was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. In a preliminary in vitro cytotoxicity bioassay, both (-)- and (+) -actisonitrile enantiomers showed cytotoxic activity against tumor and non tumor mammalian cells.