Phytochemical analysis of alkaloids from the Icelandic club moss Diphasiastrum alpinum

8S-O-acetylepiclavolonine, a new Lycopodium alkaloid, was isolated from the Icelandic club moss Diphasiastrum alpinum and its structure and stereochemistry was determined using a combination of NMR spectroscopy and mass spectrometry. The previously described alkaloids 5R,8R-O-acetylfawcettiine, 5R,8S-O-acetyllofoline, lycodoline and anhydrolycodoline were found in D. alpinum for the first time together with previously reported lycopodine and clavolonine. The 1H NMR spectra of 8S-Oacetylepiclavolonine and 5R,8S-O-acetyllofoline, revealed a highly deshielded proton at ca. 12 ppm, which seems to be stabilized by an intramolecular hydrogen bond to the carbonyl oxygen of the 8S-Oacetyl group. The isolated alkaloids were tested toward acetylcholinesterase in vitro without showing significant inhibition.