PYRROLIDINOOXAZOLIDINE ALKALOIDS FROM 2 SPECIES OF LADYBIRD BEETLES

From the mixture of alkaloids obtained from adults of two species of l adybird beetles, Epilachna varivestis and Epilachna borealis, a novel bicyclic alkaloid, 5-(12'-aminotridecyl)pyrrolidinoox-azolidine [(5 al pha,7a lpha-methylpyrrolol[2,1-b]oxazole-5-dodecaneamine] (2) was char acterized on the basis of spectrometric and synthetic investigations. This new alkaloid is related structurally to a monocyclic congener -(2 -hydroxyethyl)-2-(12'-aminotridecyl)pyrrolidine (1), previously charac terized from E. varivestis. Two additional alkaloids (lower homologs o f 1 and 2) from E. borealis were characterized as 5-(10'-aminoundecyl) pyrrolidinooxazolidine [(5 alpha,7a beta)-hexahydro-alpha-methylpyrrol o[2, 1-b]oxazole-5-decaneamine] (7) and 1-(2-hydroxyethyl)-2-(10'-amin oundecyl)pyrrolidine (8), on the basis of their mass spectra.