Identification of some L-numbered Lycopodium alkaloids

Abstract

The pioneering research on Lycopodium alkaloids carried out by R. H. F. Manske and L. Marion led to the characterization of a large number of alkaloids. Many of these alkaloids were designated by numbers preceded by an L (e.g., L1, which has since been shown to be dihydrolycopodine). While the identity of many of these alkaloids has now been established, several remain unreported. We have examined samples of alkaloids L15, L16, L17, L18, L22, L24, L25, L26, L28, L29, L31, and L35, obtained from Marion's collection, by GC–MS and GC–IR, and report herein the identity of these alkaloids and alkaloid mixtures. Most of the samples proved to be mixtures of known alkaloids. Acetylannofoline (5), a component of alkaloid L17, and 5,15-oxidolycopodane (9), a component of alkaloids L28 and L31, are identified for the first time as natural products. A complete listing of the L-numbered alkaloids is provided. Keywords: Lycopodium alkaloids, alkaloids, acetylannofoline, oxidolycopodane.