In our search for biogenetically interesting intermediates of Lycopodium alkaloids, lyconadin A (1), a novel alkaloid with an unprecedented skeleton consisting of three six-membered, one five-membered, and one α-pyridone rings, and a new alkaloid, 11-hydroxy lycodine (2), were isolated from the club moss Lycopodium complanatum. The isolation and structure elucidation of 1 and 2 were described. Lyconadin A (1) is a novel type of alkaloid consisting of five fused rings (one five-membered and four six-membered rings), while compound 2 is the first lycodine analogue with a hydroxy group at C-11. Lyconadin A (1) and 11-hydroxylycodine (2) exhibited cytotoxicity against murine lymphoma L1210 cells (IC50, 0.46 and 5.5 µg/mL, respectively) and human epidermoid carcinoma KB cells (IC50, 1.7 and >10 µg/mL, respectively) in vitro.