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五味子的化学成分研究

Studies on Chemical Constituents of Schisandra Chinensis Baill

【作者】 王丽薇

【导师】 赵昱; 周长新;

【作者基本信息】 浙江大学 , 生药学, 2004, 硕士

【摘要】 本论文主要由二章组成。第一章详细论述了五味子化学成分及其结构改造两方面的研究内容。从五味子科(Schisandraceae)五味子属植物五味子(Schisandra chinensis Baill.)的果实95%乙醇提取物中分离得到了37个化学成分,并通过MS、1H NMR、13C NMR、DEPT、HMQC、HMBC、NOESY等现代波谱技术及晶体X-衍射分析等方法,最终鉴定其中的27个化合物,包括木脂素类化合物:Kadsurarin(1),五味子甲素(2),Gomisin G(3),Gomisin D(4),Gomisin J(5),γ-schizandrin(6),五味子丙素(7),二氢愈疮木脂素(8);三萜类化合物:甘五酸(9),Nigranoic acid(10),南五味子酸(11);倍半萜类化合物:β-chamigrenic acid(12),Chamigrenal(13);生物碱类化合物:N-苯基-2-萘胺(14);甾体类化合物:β-谷甾醇(15)和有机酸(酯)类化合物:二十四烷酸(16),十四烷酸(17),富马酸单乙酯(18),柠檬酸三甲酯(19),2-羟基-丙基三羧酸-2-乙酯(20),柠檬酸(21),2-羟基-丙基三羧酸-1-乙酯(22),2-羟基-丙基三羧酸-2,3-二甲酯-1-乙酯(23),2-羟基-丙基三羧酸-1,3-二甲酯-2-乙酯(24),3-羟基-4-甲氧基-苯甲酸甲酯(25),3,4-二甲氧基苯甲酸甲酯(26),原儿茶醛(27)。其中化合物14为首次发现存在于五味子科植物中,化合物1、10、11为首次从五味子属植物中分离得到,化合物16、18、20、21、22为首次从五味子植物中分离得到。另外,我们还对化合物1进行了结构改造探索,最终得到三个新化合物:(38)5,6,7,8-四氢-1,2,13-三甲氧基-3-(烯丙氧基)-6,7-二甲基-苯并[3,4]环辛烯[1,2-f][1,3]苯并亚甲二氧;(39)5,6,7,8-四氢-1,2,13-三甲氧基-3-(4-溴-苄氧基)-6,7-二甲基-苯并[3,4]环辛烯[1,2-f][1,3]苯并亚甲二氧;(40)5,6,7,8-四氢-1,2,13-三甲氧基-3-苄氧基-6,7-二甲基-苯并[3,4]坏辛烯[1,2-f][1,3]苯并亚甲二氧。 第二章对五味子属植物的主要化学成分木脂素与三萜及其生物活性,联苯环辛二烯木脂素的波谱特征进行了简要的综述。

【Abstract】 This dissertation is composed of two chapters. The first chapter elaborates the studies on the chemical constituents of Schisandra chinensis Baill., as a result, thirty seven compounds were isolated from the 95% ethanol extract of S. chinensis, and twenty seven of them were identified on the basis of spectral evidences as well as X-ray crystallographic analysis, including Kadsurarin (1), Wuweizisu A (2), Gomisin G (3), Gomisin D (4), Gomisin J (5), y-schizandrin (6), Wuweizisu C (7), Meso-dihydro-guaiarestic acid (8), Ganwuweizic acid (9), Nigranoic acid (10), Kadsuric acid (11), Chamigremc acid (12), Chamigrenal (13); N-phenyl-2-naphthylamine (14), Sitosterol (15), Tetracosanoic acid (16), myristic acid (17), Monoethyl fumarate (18), Citric acid trimethyl ester (19), 2-hydroxy-propanetricarboxylic acid-2-ethyl ester (20), Citric acid (21), 2-hydroxy-propanetricarboxylic acid-1-ethyl ester (22), 2-hydroxy-propanetricarboxylic acid-2, 3- dimethyl ester-1-ethyl ester (23), 2-hydroxy-propanetricarboxylic acid-1, 3-dimethyl ester-2-ethyl ester (24) 3-hydroxy-4-methoxy-benzoic acid-methyl ester (25) 3, 4-dimethoxy-benzoic acid-methyl ester (26), protocatechnic aldhyde (27). Among them, for the first time, compound 14 was isolated in Schisandraceae family, Compound 1, 10 and 11 in Schisandra genus, and compound 16, 18, 20, 21, 22 in S. chinensis.Moreover, as a result of structure modification of compound 1, three new compounds were obtained including 5, 6, 7, 8-tetrahydro-1, 2, 13-trimethoxy-3-allyloxy- 6, 7- dimethyl- benzo [3, 4] cycloocta [1, 2-fj [1, 3] benzodioxole (38); 5, 6, 7, 8-tetrahydro-1, 2, 13-trimethoxy -3-(4-Bromo-benzyloxy)- 6, 7- dimethyl- benzo[3, 4] cycloocta [1, 2-f] [1, 3] benzodioxole (39); 5, 6, 7, 8-tetrahydro-1, 2, 13-trimethoxy- 3-benzyloxy-6, 7- dimethyl- benzo [3, 4] cycloocta [1, 2-f] [1,3] benzodioxole (40).The second chapter presented a review on the main chemical constituents Schisandra genus and their biological activities, as well as spectroscopic characteristics of dibenzocyclooctadiene lignans.

  • 【网络出版投稿人】 浙江大学
  • 【网络出版年期】2005年 01期
  • 【分类号】R284
  • 【被引频次】29
  • 【下载频次】2960
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