Studies On The Chemical Constituents Of Metasequoia Glyptostroboides Leaves

Metasequoia glyptostroboides is a species of plant in the genus Metasequoia in the family Taxodiaceae.Phytochemical studies have shown that M.glyptostroboides mainly contains chemical components such as terpenes,flavonoids,lignans and steroids.Some of these chemical components have antibacterial,antiviral,and antioxidant effects.M.glyptostroboides is now cultivated in a large number of areas of the country,and it is also cultivated in Kunming,Yunnan Province.In order to provide a basis for the further development of M.glyptostroboides in the field of medicinal plant applications,the chemical composition of M.glyptostroboides leaves produced in Kunming,Yunnan Province were separated and purified.After the leaves were air-dried and crushed,40 compounds were separated and identified by extraction,column chromatography and spectroscopy.The main structural types include: abietane diterpenes,labdane diterpenes,flavonoids and lignans;and other structural types include: cycloartane triterpenoids,desesquiterpenes,coumarins,quinones,simple aromatic compounds and steroids.The structures are identified as: 4,9-dehydro-metaseglyptorin A(1),cycloartane-3,24-dione(2),blumenol A(3),dehydrovomifoliol(4),sugiol(5),hinokiol(6),metaglyptin A(7),metasequoic acid A(8),3 β-hydroxyanticopalic acid(9),3 β-acetoxy-8(17),13Elabdadien-15-oic acid(10),8-hydroxy-labda-13(16),14-dien-19-yl trans-coumarate(11),ajudecunoid E(12),apigenin(13),4’-methoxytricetin(14),quercetin(15),4’-O-methyl-myricetin(16),5-hydroxy-3,7,4’-trimethoxyflavone(17),(±)-eriodictyol(18),aromadendrin(19),taxifolin(20),(+)-catechin(21),2’’,3’’-dihydrohinokiflavon(22),salicifoliol(23),lariciresinol 9’-benzoate(24),(-)-hinokinin(25),meridinol(26),8-hydroxypluviatolide(27),(-)-matairesinol(28),(-)-nortrachelogenin(29),thujastandin(30),4,4’-dihydroxy-chalcone(31),trans-hiokiresinol(32),umbelliferone(33),α-tocopherylquinone(34),terphthalic acid bis(2-ethyl-hexyl)ester(35),p-hydroxybenzaldehyde(36),p-hydroxyl-benzoic acid(37),pyrocatechol(38),β-sitosterol(39)and β-sitostenone(40).Among them,compound 1 is a new cycloartane triterpenoid,and compounds 2-4,12,14,16-19,22-24,27,31,33 and 35 are the first isolated and identified in M.glyptostroboides.At the same time,the structural modification of the active ingredients of natural products plays an important role in the development and application of new drugs.This article is a testament to M.glyptostroboides leaves contain large amounts of compounds 3 β-hydroxyanticopalic acid,3 β-acetoxy-8(17),13E-labdadien-15-oic acid,meridinol,8-hydroxypluviatolide and Inula japonica mixture were structurally modified to obtain 9 new derivatives.The structures are identified as:N-2-(indol-3-yl)-ethyl-3 β-hydroxyanticopalamide(1’),N-2-(5-methoxy-indol-3-yl)-ethyl-3β-hydroxyanticopalamide(2’),N-2-(indol-3-yl)-ethyl-3β-acetoxy-8(17),13Elabdadien-15-oiamide(3’),N-2-(5-methoxy-indol-3-yl)-ethyl-3β-acetoxy-8(17),13Elabdadien-15-oiamide(4’),meridinol hydrogenation product(5’),8-hydroxypluviatolide hydrogenation product(6’),N-2-(indol-3-yl)-ethyl-amino-2,3-dihydroaromatcin(7’),N-2-(indol-3-yl)-ethyl-amino-4H-tomentosin(8’)and N-2-(5-methoxy-indol-3-yl)-ethyl-amino-4H-tomentosin(9’).