Lycopodium serratum

Huperzia serrata (Thunb.) Trev. [= Lycopodium serratum Thunb.], Lycopodiophyta from China... 

Chen, C. H. Lee, S. S. Studies on the bioactive Lycopodium alkaloid—the structure and activity of isoselagine from Lycopodium serratum var. longipetiolatum. J. Taiwan Pharm. Assoc., 1984, 36 1-7. 

Ruscus aculeatus (butcher s broom) Veratrum species (hellebore) Strychnos nux-vomica (nux vomica) Lycopodium serratum (clubmoss)... 

Tussilago farfara (coitsfoot) Asteraceae (aster) Clubmoss Lycopodium serratum... 

Lycopodium serratum (clubmoss, Jin bu huan) has been used in Chinese medicine for more than 1000 years. It contains the alkaloid serratidine and triterpenoids, such as oxolycoclavinol, oxoserratenetriol, tohogeninol, and tohogenol. 

Details of the structural elucidation of two unusual alkaloids, serratinidine (6) from Lycopodium serratum var. serratum f serratum and fawcettidine (10) from L. fawcetti have been reported.2 Following an ingenious proposal for the bio-genetic inter-relationships of the common lycodoline (1), serratinine (2), and serratinidine (3) type structures (Scheme 1), the chemical correlation of the last two alkaloids was achieved as outlined in Scheme 2. The final product (6) was... 

This refers to L, eerratum Thunb. var. serratum form, aerratum = Lycopodium serratum Thunb. var. Thunbcrgii Makino). ° This refers to L. aerratum Thunb. var. aerratum, form, intermedium Nakai. 

Lycopodium serratum has been a rich source of alkaloids of this family, and serratidine (15 CigHasXOg) is another interesting compound... 

Huperzine A, a potent anticholinesterase alkaloid, and huperzine B were separated from a Chinese medicinal herb, Huperzia serrata (Thunb) Trev. Lycopodium serratum Thunb.), (Lycopodiaceae), by Liu et al [25]. The plant was used in Zhejiang Province of China for treatment of some mental disorders. 

Among the alkaloids in Lycopodium plants, huperzine A (2) was isolated from Lycopodium serratum Thunb. in 1986 and has been shown to have acetylcholine esterase (AChE) inhibitory activity and to improve memory disorders in Alzheimer s disease [13-15]. In addition to these unique activities, it was recently reported that some Lycopodium alkaloids possessing skeletons different from that of huperzine A (2) are able to enhance nerve growth factor (NFG) mRNA expression and production in human glial cells [16, 17]. Because of their useful biological activities, Lycopodium alkaloids are an attractive target in natural product chemistry, synthetic chemistry, and medicinal chemistry. 

Katakawa K, Kogure N, Kitajima M, Takayama H (2009) A new Lycopodium alkaloid, lycoposerramine-R, with a novel skeleton and three new fawcettimine-related alkaloids from Lycopodium serratum. Helv Chim Acta 92 445-452 and references cited therein... 

Takayama H, Katakawa K, Kitajima M, Seki H, Yamaguchi K, Aimi N (2001) A new type of Lycopodium alkaloid, Lycoposerramine-A, from Lycopodium serratum Thunb. Org Lett 3 4165 167 (2002)4 1243... 

Katakawa K, Kitajima M, Yamaguchi K, Takayama H (2006) Three new phlegmarine-type Lycopodium alkaloids, lycoposerramines-X, -Y and -Z, having a nitrone residue, from Lycopodium serratum. Heterocycles 69 223-229... 

Jiang WP, Ishiuchi K, Wu JB, Kitanaka S. Serralongamine A, a new Lycopodium alkaloid from Lycopodium serratum var Longipetiolatum. Heterocycles 2014 89 (3) 747-52. 

A series of lycoposerramines isolated by Takayama et al. were fawcettimane-type and fawcettidane-type alkaloids from the same species Lycopodium serratum in Japan which contains huperzines in China. The structure of lycoposerramine-A (21), which has a l,2,4-oxadiazolidin-5-one residue in the molecule, was elucidated through spectroscopic data and X-ray analysis (31,32). Seven new alkaloids, lycoposerramines B (22), C (23), D (24), E (25), P (26), Q (27), S (28), and U (29), with novel, fawcettimine-related structures were isolated from the club moss Lycopodium serratum in Japan (33). Their relative and absolute stereochemistries were analyzed by spectroscopic data. X-ray analysis, and chemical correlations. The skeleton of lycoposerramine A (21) may be constructed by the incorporation of NH3, NH2OH, and a Ci unit into a fawcettimine-type skeleton. 

Furthermore, ten new alkaloids, lycoposerramines F (30), G (31), H (32), I (33), J (34), K (35), L (36), M (37), N (38), and -O (39), having lycopodine-related structures, were isolated from the club moss Lycopodium serratum and their structures were elucidated on the basis of spectroscopic analysis and/or chemical transformation (34). Lycoposerramines F (30) and J (34) were the same structures as miyoshianines A and B, respectively, isolated from Huperzia miyoshiana (50). 

Lycopodium alkaloids are a class of natural products with unique ring systems, which have attracted great interest from a biogenetic point of view. These unique skeletons have prompted extensive phytochemical work and a project was initiated on the alkaloids of the club moss Lycopodium serratum var. serratum. Three new alkaloids, serratezomines A (40), B (41), and C (42), with a seco-serratinine-type, a serratinine-t)q)e, and a lycodoline-t5rpe skeleton, respectively, were isolated from the club moss L. serratum var. serratum (35). All of the structures are listed in Table I. 

Lycoposerramine-A (21), isolated from Lycopodium serratum by Takayama et al. (31,32), was biogenetically derived from fawcettimine (93) via the hypothetical route as shown in Scheme 4. The carbonyl functions at C-5 and C-13 in fawcettimine (93) were converted into hydroxylamine and imine, respectively. A-Methylation and diaminoacetal formation at C-13, followed by formation of cychc carbamate, afforded lycoposerramine-A (21). 

Huperzine A (1), isolated from the club moss Huperzia serrata (syn. Lycopodium serratum), has been used in the treatment of Alzheimer s disease (AD). The club moss... 

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