Studies On The Chemical Constituents Of Huperzia Serrata And Two Related Plants

This dissertation consists of four chapters altogether.The first chapter reported the chemical constituents from Huperzia serrata.The second chapter described the isolation and identification of chemical constituents from Diphasiastrum complanatum(L.) Holub.In the third chapter was reported the chemical constituents of the Lycopodiastrum casuarinoides(Spring) Holub.The last chapter, we summarized the naturally occuring Lycopodium alkaloids between 2004 and Febrary in 2009,and introduced the pharmacological investigation of huperzine A.As a result,52 compounds were isolated from these plants.Among them,49 compounds were identified on the basis of spectral methods,including four 4 Lycopodium alkaloids.These compounds covered Lycopodium alkaloids, triterpenoids and sterides.Huperzia serrata is one of the the most commonly encountered traditional Chinese herbal medicines for the treatment of contusions,strain,swelling and schizapophrenia.The main chemical constituents of this plant were Lycopodium alkaloids.Among them,huperzine A,which shows strong anti-acetylcholinesterase activity and increases the efficiency for learning and memory in animals.Clinically, this alkaloid is used successfully for the treatment of Alzheimer's disease and myasthenia gravis in China.In our present study,28 compounds were isolated from the MeOH extract of Huperzia serrata.Among them,25 compounds were identified including three new Lycopodium alkaloids.All the identified compounds are: macleanine(1),L20(2),lycoposerramine H(3),serratidine(4),obscurumine A(5), 11α-O-acetyllycopodine(6),huperzine A(7),huperzine B(8),huperzinine(9), N-demethylhuperzinine(10),des-N-methyl-β-obscurine(11),lycodine(12), N-methylhuperzine B(13),huperserrine A(14)~*,phlegmariurine A(15), phlegmariurine B(16),8β-hydroxy phlegmariurine B(17),lycoposerramine C(18), huperserrine B(19)~*,lycoflexine(20),lycoposerramine U(21),huperzine J(22), huperserrine C(23)~*,huperzine K(24),carinatumin C(25).Among them, compounds 14,19,23 were new compounds.Diphasiastrum complanatum Holub.,which belongs to the family Lycopodiaceae,is widely distributed in Yunnan,Sichuan,Guizhou Provinces.The whole plant has been used as a traditional Chinese herbal medicine for the treatment of arthritic pain,quadriplegia,and contusion.Phtochemical study on the whole plant of Diphasiastrum complanatum resuled in the isolation of 14 compounds.The isolated and identified compounds are:lycopodine(1),anhydrolycodoline(2),L20 (3),lycoposerramine-K(4),diphaladine A(5)~*,lycodoline(6),obscurumine A(7), lycodine(8),des-N-methyl-β-obscurine(9),des-N-methyl-α-obscurine(10), fawcettimine(11),lycoflexine(12),phlegrnariurine B(13),lycoclaninol(14). Among them,diphaladine A is a new compound and compounds 2-4,6-7,9-14 are all isolated from this plant for the first time.Lycopodiastrum casuarinoides(Spring) Holub.belonging to the family Lycopodiaceae,is widely distributed in Fujian,Guangdong,Guangxi,Guizhou and Yunnan provinces.The whole plant of Lycopodiastrum casuarinoides has been used as folk medicine for the treatment of rheumatic lumbago,arthralgia,acroanesthesia and so on.We have investigated the whole plant of Lycopodiastrum easuarinoides and lead to the isolation of 10 compounds,huperzinine(1),N-demethylhuperzinine (2),huperzinine N-oxide(3),huperzine D(4),huperzine B(5),huperserrine A(6)~*, N,N-diethylbutanamine(7),α-onocerin(8),26-nor-8-oxo-α-onocerin(9),β-sitosterol(10).Among them,compound 6 is a new compound and compounds 8,9 are two triterpenoids.The review summarized the naturally occuring Lycopodium alkaloids between 2004 and Febrary in 2009,and introduced the pharmacological investigation of huperzine A.