Canavanine

Abstract

Canavanine [2-amino-4-(guanidinooxy) butanoic acid] occurs in over 350 species of the papilionoideae, a subfamily of the Leguminosae. It is an analogue of arginine (Fig. 1). The highest concentration of canavanine (13% dry weight) has been reported in Dioclea megacarpa and it occurs up to 5% in seeds of Canavalia ensiformis. L-canavanine exhibits potent antimetabolic properties in organisms ranging from viruses and prokaryotes to whole animals. Canavanine acts primarily as an arginine antagonist and gets incorporated into the cell nucleus and other proteins and interferes with deoxyribonucleic acid and ribonucleic acid formation. In monkeys it causes hematological and serological abnormalities. These abnormalities are similar to those seen in human systemic lupus erythematosus, an autoimmune disease that adversely affects the kidney and skin. Canavanine affects the charged surface of membrane of autoimmune β cells, and it has been suggested that such alterations may be associated with abnormal autoimmune response.