Extraction And Isolation Of The Chemical Constituents Of The Seed Of Schisandra Propinqua (Wall)Hook.f.et Thoms.

Schisandra propinqua(Wall)Hook.f.et Thoms , a member of schisandraceae, mainly distributing in Yunnan and Guangxi province in China, was found in the second half of the last century and has lots of pharmacology effects, including antiheptits, antitumor, anti-HIV and platelet- activating factor antagonistic activities according to the references. It was reported that Manshanxiang Complex, a herbal medicine preparation in which the roots and stems of Schisandra propinqua (Wall)Hook.f.et Thoms are a major component, was used for treatment of lung cancer. Up to now, there were not any reports about the studies on the seed of schisandra propinqua(Wall)Hook.f.et Thoms. In order to understand the chemical constituents in it, the chemical constituents of the seed of schisandra propinqua(Wall)Hook.f.et Thoms were studied in this dissertation.This dissertation composes of two chapters. The first chapter is a review of the research progress of the plant schisandra propinqua(Wall)Hook.f.et Thoms., which mainly included its chemical constituents and pharmacology activities.The second part is about the chemical constituents of the seed of schisandra propinqua(Wall)Hook.f.et Thoms. Phytochemical investigation of 75% alcohol extract from the seed of schisandra propinqua has resulted in the isolation of twenty-three compounds. Their structures were elucidated on the basis of spectroscopic analysis, especially NMR.The seed of schisandra propinqua was extracted by 75% ethanol, and then partitioned by petrol ether, chloroform, ethyl acetate and n-butanol, respectively. The extracts of the petrol ether fraction were isolated by column chromatograph of silica gel to give five parts (P-Fr.1, P-Fr.2, P-Fr.3, P-Fr.4 and P-Fr.5). Compound 9, 10, 11, 12 and compound 13 were got from P-Fr.1 and P-Fr.2 by column chromatograph of silica gel, PTLC, recrystallization. The extracts of the chloroform fraction were separated by column chromatograph of silica gel to give five parts (C-Fr.1, C-Fr.2, C-Fr.3, C-Fr.4 and C-Fr.5). Continuing studies of C-Fr.1 have led to the isolation of compound 15 and 16 by PTLC and column chromatograph of Sephadex LH-20. Compound 17 was obtained only by recrystallization from C-Fr.2. Through column chromatograph of silica gel, large amounts of compound 14 was acquired from C-Fr.3. Compound 21 and 22 were gained on the basis of column chromatograph of silica gel, recrystallization methods from C-Fr.4. Compound 18 was purified by methanol and chloroform from C-Fr.5. The extracts of ethyl acetate fraction were subject to column chromatograph of silica gel to give five parts (E-Fr.1, E-Fr.2, E-Fr.3, E-Fr.4 and E-Fr.5). The isolation of E-Fr.1 and E-Fr.2 was to afford compound 1, 3, 4, 5, 6, 7 and 8 by column chromatograph of silica gel, PTLC and recrystallization. Compound 2, 19 and 20 were got from E-Fr.3 and E-Fr.4 by column chromatograph of silica gel and Sephadex LH-20. The separation of n-butanol extracts was to afford compound 23 by column chromatography of macro-porous adsorption resins, Sephadex LH-20, silica gel and then PTLC.On the basis of 1H NMR and 13C NMR data and by comparison of them with the references, the structures of fifteen compounds were identified , they areβ-sitosterol (3), naringenin(4), vanillic acid(5), 1,4-dihydroxy-benzene (6), ginkgetin(7), physcion(9), hexadecanoic acid (11), stearic acid(12), 6-ethyl-5- hydroxy -2,7-dimethoxy-1,4- naphthoquin- one(13), ursolic acid(14), salicylic acid (17), dauosterol(18), gallic acid(19), myricetin (20) and n-octacosane(21). Compound 8 and 23 were established as methyl salicylate 2-O-β-D- glucopy- ranoside and methyl salicylate 2-O-β-D-xylosyl(1→6)β-D- glucopyranoside on the basis of spectroscopic analysis of 1H NMR, 13C NMR, HMBC data and by comparison with the references. Compound 15 was determined by UV,¹H NMR,¹³C NMR,DEPT,H-H COSY,HSQC,HMBC,NOESY and MS. It was identified as a new compound by searching of SciFinder Scholar and named as 4β,6α-dimethyl-eremophilan-7(11),8(9)-dien-12,13(4α,6α)-diolide, and its pharmacology activities need further experiment to be checked. It needs further spectroscopic data, such as MS, H-H COSY, HSQC and so on, to determine the structures of the other five compounds. All identified compounds, exceptβ-sitosterol, were isolated from the plant for the first time.