Hupercumines A and B, Lycopodium Alkaloids from Huperzia cunninghamioides, Inhibiting Acetylcholinesterase

A novel class of C38N4 Lycopodium alkaloid, hupercumine A (1), consisting of two octahydroquinolines, a decahydroquinoline, and a piperidine, and a new C27N3-type alkaloid, hupercumine B (2), were isolated from Huperzia cunninghamioides (Hayata) Holub. The structures and absolute configurations of 1 and 2 were elucidated on the basis of spectroscopic data, chemical means, and biogenetic point of view. Hupercumines A (1) and B (2) showed moderate inhibitory activity against acetylcholinesterase.