The identification of aminoalkylphosphonyl cerebrosides in the marine gastropod, Monodonta labio.

From Monodonta labio a mixture of aminoalkylphosphonyl cerebrosides was isolated in a yield of 1.0% of the total complex lipids. The aminoalkylphosphonyl cerebrosides were found to be composed of a major portion of 1-O-[6'-O-(N-methylaminoethylphosphonyl)galactopyranosyl]ceramide and a minor portion of 1-O-[6'-O-(aminoethylphosphonyl)galactopyranosyl]ceramide. Palmitic (49.7%) and 2-hydroxy palmitic (12.2%) acids were the main fatty acid constituents and a small amount of oleic acid was also detected. The long chain bases had a characteristic pattern with 16-22 carbon chain lengths, and were classified into four groups: normal dihydroxy monounsaturated bases (40.6%), branched dihydroxy monounsaturated bases (34.0%), dihydroxy diunsaturated bases (22.0%), and trihydroxy bases (2.2%). Among them dihydroxy 18 : 1 and 18 : 2 and branched 19 : 1 bases were predominant.