Many mosses belonging to the Lycopodium, Huperzia and Phyloglossum Genus [all three belonging to the Lycopodiaceae Family] contain highly toxic quinolizidine alkaloids such as lycopodine, annotidine/annotinine, huperzine A and selagine. The alkaloids of the Clubmosses are based upon 20 differing skeletoal frameworks. Huperzine A and Selagine have a similar structural skeleton and are found in a wide variety of Clubmosses. There exist many other variations on this molecule.
Lycofoline, Lycopodine and Annotinine are all based on the Annotinine skeletal frame. Cernuine and Lycoramine on differing skeletal frameworks.
Further examples of the skeletal structures of Lycopdium alkaloids are to be found on the
Common Clubmoss page.
Huperzine A was first found in Huperzia Selago, the Fir Clubmoss featured on this page. It is an Acetylcholine inhibitor and may eventually find use in treating Alzheimers disease. Selagine could have first been found in Lesser Clubmoss, (Selaginella Salaginoides), or in Huperzia Selago.
Annotinine have much the same molecular structure, and are to be found in most Clubmosses. Lycofoline is perhaps less abundant than the other alkaloids. Once again, many other molecular variants exist.
Annotinine/Annotidine was first found in Interrupted Clubmoss (Lycopodium Annotinum) and
Cernuine in the possibly non-native Creeping Clubmoss (Lycopodium Cernuum)
Lycoramine is a rather different alkaloid with 5-, 6- and 7-membered rings found in Lycopodium Clubmosses. Lycoramine is quite similar structurally to Galanthamine which occurs in members of the Daffodil Family.