Isolation and characterization of two guanidines from Galega orientalis Lam cv Gale (fodder galega)

The vegetative parts of Galega orientalis Lam. cv. Gale, being tested in Canada as a new cold-hardy fodder crop, were found to contain two hemiterpenoid guanidines: the know alkaloid smirnovine, and its previously unknown (Z)-4-hydroxy derivative. The synthesis of smirnovine picrate is also described for the first time. A sample of G. orientalis from Estonia yielded smirnovine in similar concentrations (0.2%). Although these levels are low, more research is required to confirm that the alkaloids in fodder galega do not pose a threat to livestock in Canada.