Hupercumines A and B, <i>Lycopodium</i> Alkaloids from <i>Huperzia cunninghamioides</i>, Inhibiting Acetylcholinesterase

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