Chemical Constituents Of Huperzia Serrata (Thunb.) Trev.

Qian Ceng Ta, a traditional Chinese medicine produced from the whole plant of the club moss Huperzia serrata (Thunb.) Trev. has been used for over 1000 years in China for treatment of a number of ailments, including contusions, strains, swellings, schizophrenia, myasthenia gravis and noworganophosphate poisoning (College, 1985; Ma, 1997). It has become known worldwide as a medicinal plant since Chinese scientists discovered huperzine A (HupA) (Fig. 1) from it in the 1980s (Liu et al., 1986a, 1986b). HupA has been found to be a potent, reversible and selective acetylcholinesterase inhibitor (AChEI) (Tang et al., 1986, 1989; Tang, 1996) and is a promising drug for treatment of symptoms of Alzheimer's disease (AD) (Ma and Gang, 2004).Previous studies on constituents from the Huperzia genus led to the isolation of different compounds such as serratene-Type triterpenoids, flavones, alkaloids and steroids.During the course of our investigation for bioactive agents from the 60%EtOH extract of the whole plant of Huperzia serrata (Thunb.) Trve which have exacted the alkaloids using Hcl solvent, 28 compounds were obtained by using silica gel column chromatography, Sephadex LH-20 chromatography, MPLC, and Semi-HPLC,, and structures of 20 compounds were elucidated through spectroscopic analysis (NMR, MS and IR ). Their structures were identified to beβ-sitosterol, CH3CH2(CH2)27CH2OH(HC-9), Podophyllotoxin , Lupeol ,Physcion(HC-25), Apigenin(HC-13), 5, 7, 2′,4'-Tetrahydroxy -5'-methoxyflavone ( HC-12 ) , 5, 7, 4′-trihydroxy-3'- methoxyflavone(HC-3), 5, 7, 4′-trihydroxy-3' , 5'-dimethoxyflavone(HC-2), 3β-hydroxyserrat-14-en-21α-ol(HC-1), 16-oxo-21β-hydroxyserrat-14-en-3α- yl-acetate (HC-4), 3β-hydroxyserrat-14-en-21β-ol ( HC-5 ) , 21α-hydroxyserrat- 14-en-3β- yl-acetate(HC-7), Serratinol B(HC-10), 3β-acetoxy-serrat-14-en-21-on-3- hydroxyserratenonacetat(HC-16), 3,5-dihydroxy-pyran-4-one(HC-16), 16-oxo-21β- hydroxyserrat-14-en-3α-ol (HC-18), 16-oxo-21β-hydroxyserrat-14-en-3β-ol(HC-19), 3?,21α-dihydroxy-serrat-14-en-24-ol(HC-20) , 3?, 21?-dihydroxy- serrat-14- en-29-ol(HC-23), 3α,21?-dihydroxy-serrat-14-en-24-ol(HC-24), 16-oxo-3α,21β- dihydroxyserrat-14-en-24-ol(HC-25). Among them, HC-16 was a new compound, HC-2,HC-3,HC-12,HC-13 and HC-25 were isolated from this plant for the first time.