Studies On The Alkaloid Constituents Of Five Species Of Lycopodium

The dissertation is composed of six chapters.In chapter 1,we summarized the progress in the research of the bioactivities of Lycopodium alkaloids since 2011.In chapter 2 we described the isolation and identification of chemical constituents from Lycopodium japonicum Thunb.ex Murray.In chapter 3 phytohemical studies of Lycopodiastrum casuarinoides(Spring)Holub were discussed.In chapter 4 phytohemical studies of Diphasiastrum complanatum(L.)Holub were reported.In chapter 5 we described the chemical constituents from Phlegmariurus phlegmaria(L.)Holub.Phytohemical studies of Huperzia serrata(Thunb.ex Murray)Trev.were discussed in chapter 6.129 Lycopodium alkaloids were isolated and identified by means of various chromatography methods and spectroscopic evidences from these plants,among which 31 compounds were new.The review summarized the progress in the research of the bioactivities of Lycopodium alkaloids from January 2011 through February 2015.Lycopodium japonicum Thunb.ex Murray,belonging to the family Lycopodiaceae,is a traditional Chinese medicinal plant for the treatment of sprains,strains and myasthemia.Investigation on this plant of two batches led to the isolation of 44 compounds,including 12 new ones,namely N-methylhydroxypropyllycodine(1)*,N-methyllycodine(2),huperzinine(3),?-obscurine(4),?-obscurine(5),des-N-methyl-?-obscurine(6),acetyllycoposerramine M(7),lycodoline(8),lycoposerramine M(9),lycoposerramine G(10),flabelliformine(11),miyoshianine A(12),12-epilycodoline-N-oxide(13),lucidioline(14),lycoposerramine C(15),lycoflexine(16),lycojaponicumin E(17),(15R)-14,15-dihydroepilobscurinol(18),lycocernuine(19),lycoponicumine A-K(20-30)*,deacetyllycoclavine(31),6a-hydroxylycopodine(32),lycoclavine(33),lycopodine(34),lycopodatine C(35),lycoposerramine K(36),5-acetyllycofoline(37),lycoflexine N-oxide(38),14,15-dehydrolycoflexine(39),lobscurinol(40),(15R)-5?-hydroxy-14,15-dihydroepilobscurinol(41),palhinine A(42),lycopoclavamine A(43),cermizine B(44).Lycopodiastrum casuarinoides(Spring)Holub,a climbing plant distributed mainly in southern China,is a single species genus belonging to the family Lycopodiaceae.Phytochemical studies on this plant of two batches resulted in the isolation of 12 compounds,including 3 new ones,namely 11?-methoxy-huperzine B(1)*,16-oxohuperzinine(2)*,huperzinine N-oxide(3),huperzine D(4),casuarinine A(5),huperzine B(6),casuarinine B(7),huperzinine(8),N-methyllycodine(9),4?-hydro-5?,6?-dihydroxy-12-epi-des-N-methyl-?-obscurine(10)*,lycodine(11),huperzine C(12).Diphasiastrum complanatum(L.)Holub,belonging to the family Lycopodiaceae,is widely distributed in tropical and subtropical areas.14 compounds were isolated from this plant,of which 4 ones were new,namely 15-epilycopodatine C(1)*,lycopodine N-oxide(2)*diphasiadine A(3)*,flabelline(4),lycopodatine C(5),lycopodine(6),acetyldihydrolycopodine(7),lycoclavine(8),6?-hydroxylycopodine(9),flabelliformine(10),lycodoline(11),lucidioline(12),des-N-methyl-?-obscurine(13),hydroxypropyllycodine(14).Phlegmariurus phlegmaria(L.)Holub(Huperziaceae)is a traditional Chinese medicinal plant for the treatment of rheumatic pain,arthritis and traumatic injury,mainly distributed in Taiwan,Guangdong,Guangxi,Hainan and Yunnan Provinces.In our study on this plant,5 compounds were isolated,2 of which were new,namely 4?-hydroxynankakurine B(1)*,?13,N?-Methyl-phlegmarine-N?-oxide(2)*,lycoposerramine E(3),nankakurine B(4),lobscurinol(5).Huperzia serrata(Thunb.ex Murray)Trev.(Huperziaceae),well known as qian ceng ta in China,is a traditional Chinese herb medicine for the treatment of contusions,strains,swellings,burns and snake bite for a long history.Since huperzine A was discovered in the 1980s by Chinese scientists(Xu Z L,Liu J S,et al.),and be found to be a potent,reversible and selective acetylcholinesterase inhibitor,there was a great wave of research be set off on Lycopodium(sensu lato).The whole plant of Huperzia serrata was investigated and 54 compounds were isolated including 11 new ones,namely huperratine A-K(1-11)*,lycopodine(12),6?-hydroxylycopodine(13),lycodoline(14),12-epilycodoline(15),6?-hydroxy-5,15-oxide-lycopodane(16),6?-hydroxy-5,15-oxide-lycopodane(17),huperzine F(18),serratidine(19),serratezomine C(20),lycoposerramine O(21),lucidioline(22),deacetyl-lycoclavine(23),fawcettimine(24),alopecuridine(25),macleanine(26),phlegmariurine A(27),phlegmariurine B(28),lycoposerramine E(29),7a-hydroxyphlegmariurine B(30),8?-hydroxyphlegmariurine B(31),8a-hydroxyphlegmariurine B(32),huperzine T(33),lycodine(34),N-methylycodine(35),huperzine B(36),N-methyhuperzine B(37),?-obscurine(38),des-N-methyl-a-obscurine(39),huperzine C(40),huperzine A(41),lycoflexine(42),lycoposerramine U(43),lycoposerramine D(44),huperratine L(45),huperratine M(46),lycoposerramine S(47),phlegmarine(48),N?-methylphlegmarine(49),lycoposerramine X(50),huperzine J(51),luciduline(52),huperzinine C(53),phlegmariurine N(54).Biological activity screening of these compounds is still in progress.