A study of the alkaloids of Lycopodium annotinum L.

Abstract

A more efficient, reliable and reproducible scheme for the quantitative concentration and separation of the alkaloids of Lycopodium annotinum L. has been developed. This scheme involves successive countercurrent distributions using the system chloroform-buffer. The pH values of the buffers are selected, utilizing determined or calculated partition data of the alkaloids. The use of chromatography on buffered paper, as well as by ion-exchange and buffered Celite partition columns, for the separation of the alkaloids of Lycopodium annotinum L. has also been studied. A new alkaloid, lycodine, C17H24N2, m.p. 118°, has been isolated from Lycopodium annotinum L.. Lycodine is a tetracyclic diacidic base containing a secondary nitrogen, a 2,3-disubstituted pyridine ring and a C-methyl group, The 2,3-disubstitution is in the form of a saturated six-membered ring. It is believed that the carbon in the C8 position, adjacent to the pyridine ring, has two hydrogen atoms attached.