Lycopodium cernuum

The same authors (1948) have isolated nicotine and the two following alkaloids from Lycopodium cernuum L. —... 

Lycopodium Alkaloids.—It has been suggested that lycopodine (16), cernuine (17), and related alkaloids are modified dimers of pelletierine (15) (Scheme 3). Lysine and acetate serve as specific precursors of lycopodine. Further, [2- " C]lysine has been specifically incorporated into cernuine (17) in Lycopodium cernuum The data suggest that this alkaloid, like lycopodine, is biosynthesised... 

C16H26N2O, Mr 262.40, mp. 103-104°C, [a]n -20.5° (CH3OH). Alkaloid from some Lycopodiaceae species ( ciubmosses. Lycopodium cernuum and L. carolia-num). It is weakly toxic. The biosynthesis starts from lysine with cadaverine, 1-piperideine, and pelletie-rine as intermediates. ... 

Work on the biosynthesis of lycopodine (126) in Lycopodium tristachyum and cernuine (127) ° in L. cernuum, previously published in preliminary form and reviewed,has appeared in full lycopodine and cernuine.It was established that the two alkaloids are derived from two molecules of lysine via a symmetrical intermediate which is in all probability cadaverine. The hypothesis that the Lycopodium alkaloids were modified dimers of pelletierine (125) (Scheme 12) required reappraisal, as pelletierine gave only one each (shown with heavy bonding) of the two CgN units of (126) and (127). 

In the course of their examination of Lycopodium species Marion and Manske 12) examined L. cernuum from which they isolated cernuine, C16H26X2O, and a second base which they designated L33. In 1964 Ayer et al. in a reexamination of the alkaloids of this species isolated the same compounds (24). They confirmed the formula of cernuine and assigned the formula C16H26N2O2 to the second base to which they gave the trivial name, lycocemuine. Both alkaloids had one basic nitrogen atom and both formed methiodides with 1 mole of methyl iodide indicating that each was a tertiary base. The IR-spectrum of cernuine had... 

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