LYCOPODIUM ALKALOIDS: III. FUNCTIONAL GROUPS OF SOME MINOR ALKALOIDS OF L. ANNOTINUM

Abstract

Four minor alkaloids of L. annotinum have been examined by chemical methods and infrared spectroscopy for their functional groups. Acrifoline (L.27) C 16 H 23 O 2 N has a double bond, a carbonyl group, and an hydroxyl function. Annotine (L.11) C 16 H 21 O 3 N has a double bond, a carbonyl group, an hydroxyl function, and an inert oxygen probably present in an ether linkage. Alkaloid L.12 (C 18 H 25 O 3 N) is O-acetylacrifoline. Alkaloid L.8 (C 16 H 25 O 2 N) has only been studied by infrared spectroscopy where it shows carbonyl and hydroxyl absorption. All four alkaloids therefore contain a basic tetracyclic ring system as do the majority of other lycopodium alkaloids. Annotoxine, a molecular compound of acrifoline and annotine, has been isolated from extracts of Canadian plant material.