Studies On The Structural Elucidation Of Chemical Constituents From Schisandra Chinensis.

The plant of Schisandraceae includes the genus Schisandra and Kadsura,which are mainly distributed in China,Korea,Japan,Rusia,and America.In China,there are 29 species distributed mostly in Yunnan and Sichuan Province.The Schisandraceae pl ant have been used for the treatment of cough,asthma,night sweat and so on.The P harmacopoeia includes the dried and mature fruits from Schisandra chinensis(Turcz)Baill.and Schisandra sphenanthera Rehd.et Wils.,the former of which is called “B eiwuweizi”,and the latter is called “Nanwuweizi”.Modern research shows that lignans and triterpenoids are main chemical consitituents of the S.chinensis which show various pharmacological activities.Lignans have p rotective effects for liver and central nervous system,inhibitory effects on cAMP,antiinflammatory,anti-gastriculcer activities and so on and triterpenoids have anti-cancer and anti-virus activities.The nortriterpenoids with novel skeleton and high oxidation de gree have aroused great interest of botanists,synthetic chemists and pharmacologists.S o,we selected the S.chinensis from Shennongjia area of Hubei Provoince and system atically study its chemical constituents.In the present study,59 compounds including 17 new compounds were isolated and purified through column chromatography,semi-HPLC and then identified by NMR,MS,X-ray single crystal diffraction,CD,calculated ECD,and residual dipolar coupling(RDC)method.The new coupounds include 6’-Opara-hydroxybenzoyl salidroside(18),Rhamnose-4-(3-hydroxypropyl)-2-methoxyphenyl(19),Schisandlignan E(29),Schisandlignan F(30),Schinalactones D(34),Schisanlact one I(35),Schisanlactone J(36),Schinchinenlactone E(37),Schinalactones E(41),(6R)-3,6-dihydroxy-2,6-dimethyl-tetralone(48),(6S)-3,6-dihydroxy-2,6-dimethyl-tetralone(49),(1S,2S)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4,5-trimethoxybenzoate(54),(1R,2R)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4,5-trimethoxybenzoate(55),(1S,2S)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-dimethoxybenzoate(56),(1R,2R)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-dimethoxybenzoate(57),(1S,2R)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-dimethoxybenzoate(58),(1R,2S)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-dimethoxybenzoate(59).The types of the isolated compounds cover the simple aromatics compounds 4-methylphenol(1),4-hydroxybenzaldehyde(2),2,4-dimethoxybenzaldehyde(3),Beta-hydroxypropiovanillone(4),Vanillin(5);the flavones compounds Pinocembrin(6),8-aldehyde-epicatechin(7),8-aldehyde-catechin(8);the flavonoid glycosides compounds Kaempferol-3-O-(6’’-O-acet yl)-β-D-glucopyranside(9),Isorhamnetin-3-O-(6’’-acetyl)-β-D-glucopyranoside(10),Querc etin-3-O-(6’’-O-acetyl)-β-D-glucopyranoside(11),Kaempferol-3-β-D-(6-O-trans-p-coumaryl)glucopyranoside(12),Kaempferol-3-O-(6-O-caffeyl)-β-D-glucopyranoside(13),Afzelin(14),Quercetin-3-O-α-L-rhamnopyranoside(15),Astragalin(16),Quercetin-3-glucoside(17);the glycosides compounds 6’-O-para-hydroxybenzoyl salidroside(18),Rhamnose-4-(3-hydroxypropyl)-2-methoxyphenyl(19);the furofuran lignans compounds Pinoresinol(20),Syringaresinol(21),Balanophonin B(22),8-Hydroxypinoresinol(23),Prinsepiol(31);the tetrahydrofuran lignans compounds Schiglaucin A(25),Dihydrocubebin(32);the arylnaphthalene lignans compounds 4,4-di(4-hydroxy-3-methoxyphenly)-2,3-dimethylb utanol(28),(+)-Isolariciresinol(33);the neolignans compounds 3-[2-(4-Hydroxy-3-meth oxyphenyl)-3-(hydroxylmethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]propyl acetate(26),Dehydroconiferyl alcohol(27);the 7,8-ring opening lignans compounds Schisandlig nan E(29),Schisandlignan F(30);the norlignans compound(±)-Salicifoliol(24);the l anostane triterpenoid compound Schisanlactone I(35);the cycloartane triterpenoids com pounds Schinalactones D(34),Schisanlactone J(36),Schinchinenlactone E(37),Kadsu philactone B(38),Schisanlactone C(39),Chinchinenlactone A(40),Schinalactones E(41),Renchanglactone A(42),Cisanlactone B(43);the sesquiterpene compound(3R*,3a S*,8S*,8a S*)-1,2,3,3a,6,7,8,8a-Octahydro-8-hydroxy-8a-methyl-3-(1-methylethyl)-5-azulen emethanol(44);and the others Benzenepropanoic acid(45),Anomallenodio(46),Arist elegone A(47),(6R)-3,6-dihydroxy-2,6-dimethyl-tetralone(48),(6S)-3,6-dihydroxy-2,6-di methyl-tetralone(49),(±)-eritro-1-(3,4,5-trimethoxy)-1,2-propanodiol(50),Sesquichamaenol(51),Dibutylphthalate(52),2-(4-Hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyp henyl)-3-oxo-1-propanol(53),(1S,2S)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4,5-trimethoxybenzoate(54),(1R,2R)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4,5-trimethoxybenzoate(55),(1S,2S)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-d imethoxybenzoate(56),(1R,2R)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-dim ethoxybenzoate(57),(1S,2R)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-dimeth oxybenzoate(58),(1R,2S)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl-3,4-dimethoxy benzoate(59).The cytotoxicity of the compounds Schinalactones D(34),Schisanlactone I(35),Schisanlactone J(36),Kadsuphilactone B(38),Schisanlactone C(39),Chinchinenlactone A(40)was further tested against Hep-G2 cell lines,but no apparent antitumor activity were observed.