α-(Methylenecyclopropyl)glycine from Litchi seeds

Abstract

L-[alpha]-(Methylenecyclopropyl)glycine has been newly characterized as a component of a higher plant being isolated from seeds of Litchi chinensis. [alpha]-(Methylenecyclopropyl) glycine was converted by catalytic hydrogenation in the presence of platinum oxide into a mixture of leucine, isoleucine, norleucine and 2 isomeric [alpha]-(methyl,-cyclopropyl)glycines. The infrared and nuclear magnetic resonance spectra of the new compound supported the assigned structure. [alpha]-(Methylenecyclopropyl)glycine showed hypoglycaemic activity when injected subcutaneously into mice. No exact comparison of the hypoglycaemic activities of the new acid and its higher homologue, hypoglycin A, was made.