Four new Lycopodium alkaloids (1-4), together with 15 known ones, were isolated from club moss Phlegmariurus squarrosus. Notably, 8α-hydroxylycojapodine A (1) was the first derivative of lycojapodine A (5) which was a novel C16N-type Lycopodium alkaloid with an unprecedented 6/6/6/7 tetracyclic ring system. Their structures were elucidated based on the spectroscopic data, including 1D and 2D NMR techniques.
Keywords: 11β-acetoxyl-N-methylhuperzine B; 8α-hydroxylycojapodine A; 8β-acetoxy-12β-hydroxy-epidihydrolycopodine; 8β-acetyllycoposerramine-U; Lycopodium alkaloids; Phlegmariurus squarrosus.