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Abstract The club moss family Lycopodiaceae produces a diverse array of bioactive lycopodium alkaloids (LAs). In particular, the alkaloid huperzine A (hupA) has grasped attention since it is a potent acetylcholinesterase inhibitor of medical interest in Alzheimer's disease. Although the structural diversity and bioactivities of LAs have been studied to some extent, their chemotaxonomic value is mostly unexplored, especially to a lower taxonomic unit (e.g. subspecies or genotypes). This study focused on previously reported Icelandic Huperzia selago genotypes, and aimed to evaluate the chemotaxonomic value of LAs in resolving them. Using liquid chromatography-mass spectrometry (LC-MS), alkaloid fingerprints of H. selago taxa were subjected to principal component analysis (PCA). Our results revealed that each genotype tends to have its own alkaloid profile. Genotype 1 and 3 form distinct groups in a PCA plot, where genotype 2 is an intermediate between the other two genotypes. HupA and its derivative, huperzine B, both contribute to the differentiation of genotype 3 from the others. Therefore, our study demonstrated the potential of alkaloid fingerprints in resolving deep taxonomic groups and selecting plant taxa of medicinal importance. Graphical abstract Image 1 Highlights • Alkaloid fingerprinting of Icelandic Huperzia selago was performed using LC-MS. • A hidden diversity of lycopodane-type alkaloids is revealed in H. selago. • Principal component analysis shows genotype-specific groups. • Alkaloid fingerprinting could resolve club moss taxa at subspecies level. [ABSTRACT FROM AUTHOR]

A new natural product, named selagoline, and two known alkaloids, huperzine A and serratidine, were isolated from Huperzia selago (Lycopodiaceae) collected in Iceland. Their structures were determined using 600 and 800MHz one- and two-dimensional NMR methods supported by Fourier-transform mass spectrometry. Possible role of selagoline as a precursor of 5,15-oxidolycopodane, a component of the classical alkaloids L28 and L31, is discussed. [ABSTRACT FROM AUTHOR]