Lycopodine‐Type Lycopodium Alkaloids from Huperzia serrata

Eleven Lycopodium alkaloids with a lycopodine‐type skeleton were isolated from the basic material of the whole plant of Huperzia serrata (T hunb .) T rev. (Huperziaceae). Among them, 12‐epilycodoline N ‐oxide (=(12 α ,15 R )‐12‐hydroxy‐15‐methyllycopodan‐5‐one N ‐oxide; 1 ), 7‐hydroxylycopodine (=(15 S )‐7‐hydroxy‐15‐methyllycopodan‐5‐one; 2 ), and 4,6 α ‐dihydroxylycopodine (=(6 α ,15 R )‐4,6‐dihydroxy‐15‐methyllycopodan‐5‐one; 3 ) are new compounds. Their structures were identified spectroscopically, especially by means of 1D‐ and 2D‐NMR.