New phlegmarane-type, cernuane-type, and quinolizidine alkaloids from two species of Lycopodium

Two new phlegmarane-type alkaloids, cermizines A () and B (), three new quinolizidine alkaloids, cermizine C () and senepodines G () and H (), and a new C16N2 type alkaloid consisting of a quinolizidine and a piperidine ring, cermizine D (), as well as two new cernuane-type alkaloids, cernuine N-oxide () and lycocernuine N-oxide (), have been isolated together with cernuine () and lycocernuine () from the club moss Lycopodium cernuum and L. chinense. The relative stereochemistry of and , and the absolute stereochemistry of , , and were elucidated by combination of NOESY correlations, modified Mosherʹs method, chemical transformations, and computational methods. Cermizine D () might be a biosynthetic intermediate of cernuane-type alkaloids such as .