Isolation, crystal structure and synthesis of arsenobetaine, a constituent of the western rock lobster, the dusky shark, and some samples of human urine

Abstract

Arsenobetaine has been isolated from the tail muscle of the western rock lobster (Panulirus cygnus George) and from the flesh of the dusky shark (Carcharhinus obscurus Le Sueur), both of which are commercially important seafoods. Trigonelline has also been isolated from the lobster and both arsenobetaine and trigonelline have been isolated from human urine obtained after ingestion of cooked rock lobster. The crystal structures of the monohydrates of arsenobetaine and trigonelline have been determined and a simple synthesis of arsenobetaine has been developed.