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题名: 轮叶棘豆、镰形棘豆、桑白皮化学成分及抗HBV、HSV-1生物活性研究
作者: 姚淑英
学位类别: 硕士
答辩日期: 2007-05-23
授予单位: 中国科学院昆明植物研究所
授予地点: 昆明植物研究所
导师: 陈纪军
关键词: 轮叶棘豆 ; 镰形棘豆 ; 桑白皮 ; 化学成分 ; 抗HBV ; 抗HSV-1 ; 生物活性
学位专业: 药物化学
中文摘要: 本论文由五章组成,第一、二、三章分别介绍了轮叶棘豆(Oxytropis chiliophylla Royle)、镰形棘豆(Oxytropis falcate Bunge)及桑白皮(Morus alba L.)乙酸乙酯部分的化学成分研究。第四章对从轮叶棘豆、镰形棘豆及桑白皮中分得的部分化合物进行抗HBV、HSV-1及抗口腔微生物活性研究。第五章对近年来报道具有抗HBV活性的天然化合物进行了综述。 利用各种色谱分离技术,从上述三种植物中分离得到35个化合物,经1D、2D NMR、MS、HRMS、IR、UV等波谱数据分析,鉴定了化合物结构,包括32个不重复的化合物,其中1个新化合物。活性研究发现:2个化合物具有一定的抗HBV活性;6个化合物具有一定的抗HSV-1活性;4个化合物具有一定的抗口腔微生物活性。 第一章 轮叶棘豆的化学成分 轮叶棘豆Oxytropis chiliophylla Royle为豆科棘豆属植物轮叶棘豆的全草,是常用藏药。我们对采自喜玛拉雅山(5700m)的轮叶棘豆全草进行化学成分研究,应用各种色谱分离技术从中分离了10个化合物,经波谱数据分析分别鉴定为:azukisapogenol(1),(22E, 24R) - 24 - 甲基 - 5α - 胆甾 - 7, 22 - 二烯 - 3β, 5α, 6β - 三醇((22E, 24R) - 24 - methyl - 5α - cholesta - 7, 22 - diene - 3β, 5α, 6β - triol ,2), 芹菜素 (apigenin,3),3′ , 4′- 二甲氧基 - 槲皮素 - 3 - O - β - D - 半乳糖吡喃苷(3′, 4′ - dimethoxy - quercetin - 3 - O - β - D - galactopyranoside ,4),7, 4′ - 二甲氧基 - 槲皮素 - 3 - O - α - L - 鼠李糖基(1→2)- β - D - 葡萄糖吡喃苷(7, 4′ - dimethoxy - quercetin - 3 -O - α - L - rhamnopyranosyl - (1→2) - β - D - glucopyranoside,5),鼠李素 – 3 –O – 槐糖苷(rhamnazin - 3 - O - sophoroside,6),rhamnazin - 3 - β - glucopyranosyl - (1→5) - α - arabinofuranoside(7),(2S, 3S, 4R)- N - {(R) - 2′ - 羟基二十四烷醇基} - 1, 3, 4 – 三羟基 - 2 - 氨基 - 十八 - 6 - 烯((2S, 3S, 4R)- N - {(R) - 2′ - hydroxytetracosanoyl} - 1, 3, 4 - trihydroxy - 2 - amino - octadeca - 6 - ene ,8),β - 谷甾醇(β - sitosteriol ,9),胡萝卜苷(daucosterol,10)。所有化合物均为首次从该植物中分得。 第二章 镰形棘豆的化学成分 镰形棘豆(Oxytropis falcate Bunge)系豆科棘豆属植物,产于青藏高原的青海、甘肃南部、四川西部。我们对采自喜玛拉雅山5 700m处的镰形棘豆的化学成分进行了研究,利用各种色谱柱层析技术,从中分离了14个化合物,经波谱分析分别鉴定为:( - ) - 7 - 甲氧基 - 二氢黄酮(( - ) - 7- methoxy - dihydroflavone,1)、( - ) - 5 - 羟基 - 7 - 甲氧基 - 二氢黄酮(( - ) - 5 - hydroxy - 7 - methyoxy - dihydroflavone,2)、( - ) - pinocembrin(3)、(-)- 7 - 羟基 - 二氢黄酮(( - ) - 7 - hydroxy - dihydroflavone ,4)、4′ - 甲氧基 - 2′ - 羟基 - 查尔(4′ - methoxy - 2′ - hydroxy - chalcone,5)、2′ , 4′ - 二羟基 - 二氢查尔酮(2′, 4′ - dihydroxy - dihydrochalcone,6)、2′,4′ - 二羟基查尔酮(2′, 4′ - dihydroxy – chalcone,7)、( - ) - maackiain (8)、tetrahydroflemichapparin - B (9)、dalbergin(10)、N - 苯甲酰基 - 2 - 苯基乙胺(N - benzoyl - 2 - phenylethylamine,11),正二十四烷醇(n - tetracosanol,12),4′ - 甲氧基 - 槲皮素 - 3 - O - α - L - 鼠李糖基(1→2)- β - D - 葡萄糖吡喃苷(4′ - methoxy - quercetin - 3 - O - α - L - rhamnopyranosyl - (1→2) - β - D - glucopyranoside,13)、β - 谷甾醇(β - sitosterol,14)。所有化合物均为首次从该植物中分得。 第三章 桑白皮的化学成分 桑白皮为桑科植物桑Morus alba L.的干燥根皮,属传统中药。本论文主要对桑白皮醇提物乙酸乙酯部分进行化学成分研究,采用多种柱层析方法从中分离了11个化合物,应用波谱方法分别鉴定为:isotetrapterol A(1)、桑白皮素(morusin,2)、环桑黄酮(cyclomorusin,3)、mulberrofuran G (4)、cyclomulberrin(5)、sigmoidin A(6)、二十五烷酸 - α - 单甘油酯(glacerol - α - pentacosannoat,7)、白桦酯酸(betulinic acid,8)、熊果酸(ursolic acid,9),β - 谷甾醇(β - sitosterol,10),胡萝卜苷(daucosterol,11)。其中化合物1为新化合物,化合物6为首次分得。 第四章 轮叶棘豆、镰形棘豆及桑白皮的生物活性 对三种植物提取物进行体外抗HBV、HSV-1及口腔微生物活性筛选,研究发现:镰形棘豆中化合物( - ) - 5 - 羟基 - 7 - 甲氧基 - 二氢黄酮(( - ) - 5 - hydroxy - 7 - methyoxy - dihydroflavone,2)及2′ , 4′ – 二羟基二氢查尔酮(2′, 4′ - dihydroxy dihydrochalcone, 6)有较好的抗HBsAg作用,其IC50分别为0.335mg/mL及<0.021mg/mL,其SI分别为 >4及>2.67,化合物dalbergin(10)及4′ - 甲氧基 - 槲皮素 - 3 - O - α - L - 鼠李糖(1→2)- β - D - 葡萄糖吡喃苷(4′ - methoxy - quercetin - 3 -O - α - L - rhamnopyranosyl - (1→2) - β - D - glucopyranoside, 13)有一定的抗HBsAg作用,其IC50分别为0.045mg/mL及>1.211 mg/mL,其SI分别为1.36及>1.121;轮叶棘豆中黄酮类化合物芹菜素(apigenin,3)抑制HSV-1的MIC值为27.27μg/ml,镰形棘豆中化合物( - ) - pinocembrin (3)、(-)- 7 - 羟基 - 二氢黄酮(( - ) - 7 - hydroxy - dihydroflavone ,4)、4′ - 甲氧基 - 2′ - 羟基 - 查尔酮(4′ - methoxy - 2′ - hydroxy - chalcone,5)以及dalbergin (10)表现出一定的抑制HSV-1病毒作用,MIC分别为74.4、81.9、82.0、84.5、85.0μg/mL。桑白皮中化合物桑白皮素(morusin,2)、mulberrofuran G(4)、cyclomulberrin(5)有较好的抗HSV-1活性,其MIC值分别为7.74、23.5及10.06μg/mL;桑白皮中分得的化合物桑白皮素(morusin,2)、环桑黄酮(cyclomorusin,3)、mulberrofuran G(4)、cyclomulberrin(5)均具有较好的抗口腔微生物活性,其中化合物2、4活性优于阳性对照。 第五章 抗HBV天然活性化合物综述 本章包括67篇文献,概述了抗HBV药物筛选的体内外研究模型,综述了1990年至2007年发表的包括木脂素及多酚类、黄酮类、生物碱类、萜类及香豆素类等共77个抗HBV天然活性化合物的结构以及抗HBV活性数据。
英文摘要: This thesis is composed of five chapters, in which constituents from three plants, Oxytropis chiliophylla Royle, Oxytropis falcate Bunge and Morus alba L had been isolated.The fourth chapter focused on the bioassay of anti - HBV, anti - HSV-1 and anti - microbial compounds from the three plants. The last chapter summarized the active anti - HBV compounds from natural products. Thirty - five compounds, including thirty - two different compounds and one new compounds, were isolated from the above three species. Their stuctures have been elucidated on the basis of extensive spectral analyses (1D, 2D, MS, IR, UV, HRMS). Bioassay on the isolated compounds showed that: 2 compounds presented anti - HBV activities; 6 compounds presented anti - HSV-1 and 4 compounds presented antimicrobial activities. Chapter 1 Chemical constituents from Oxytropis chiliophylla The whole plant of Oxytropis chiliophylla is used as Chinese herb. Chemical investigation on O. chiliophylla led to the isolation of 10 compounds for the first time and identified as follows based on spectral anylyses: 1. azukisapogenol (1) 2. (22E, 24R) - 24 - methyl - 5α - cholesta - 7, 22 - diene - 3β, 5α, 6β - triol (2) 3. apigenin (3) 4. 3′, 4′ - dimethoxy - quercetin - 3 - O - β - D - galactopyranoside (4) 5. 7, 4′ - dimethoxy - quercetin - 3 -O - α - L - rhamnopyranosyl - (1→2) - β - D - glucopyranoside (5) 6. rhamnazin - 3 - O - sophoroside (6) 7. rhamnazin - 3 - β-glucopyranosyl - (1→5) - α - arabinofuranoside (7) 8. (2S, 3S, 4R) - N - {(R) - 2′ - hydroxytetracosanoyl} - 1, 3, 4 - trihydroxy - 2 - amino - octadeca - 6 - ene (8) 9. β - sitosterol (9) 10. daucosterol (10) Chapter 2 Chemical constituents from Oxytropis falcate Oxytropis falcate Bunge, belonging to the Leguminosae family, is distributed in the Qinghai, southern of Gansu and western of Sichuan province. Chemical investigation on the whole plant of O. falcate collected in Himalayas mountain(5700m) led to the isolation of 14 compounds for the first time and identified as follows: 1. (- ) - 7- methoxy - dihydroflavone (1) 2. ( - ) - 5 - hydroxy - 7 - methyoxy - dihydroflavone (2) 3. ( - ) - pinocembrin (3) 4. ( - ) - 7 - hydroxy - dihydroflavone (4) 5. 4′ - methoxy - 2′ - hydroxy - chalcone (5) 6. 2′, 4′ - dihydroxy - dihydrochalcone(6) 7. 2′, 4′ - dihydroxy - chalcone(7) 8. ( - ) - maackiain (8) 9. tetrahydroflemichapparin - B (9) 10. dalbergin(10) 11. N - benzoyl - 2 - phenylethylamine (11) 12. n - tetracosanol (12) 13. 4′ - methoxy - quercetin - 3 - O - α - L - rhamnopyranosyl - (1→2) - β - D - glucopyranoside (13) 14. β - sitosterol (14) Chapter 3 Chemical constituents from Morus alba L “Sangbaipi”, the root bark of Morus alba L. is used as a traditional Chinese medicine. Researching on the constituents of Morus alba, 11 compounds were isolated by chromatography method. Among of them, one new compound was elucidated. By means of spectral data and mass analyses, the isolates were identified as follows: 1. isotetrapterol A (1*) 2. morusin (2) 3. cyclomorusin (3) 4. mulberrofuran G(4) 5. cyclomulberrin(5) 6. sigmoidin A (6▼) 7. glacerol - α - pentacosannoat(7) 8. betulinic acid (8) 9. ursolic acid(9) 10. β -sitosterol (10) 11. daucosterol(11) NOTE: *new compounds ▼isolated for the first time Chapter 4 Bioactivities of Oxytropis chiliophylla, Oxytropis falcate and Morus alba Bioassay on compounds from the three plants, Oxytropis chiliophylla, Oxytropis falcate and Morus alba was investigated on the model of anti - HBV, Anti - HSV-1 and antimicrobial. Several active compounds were revealed, (-) - 5 - hydroxy - 7 - methyoxy - dihydroflavone(2) and 2′, 4′ - dihydroxy - dihydrochalcone (6) from Oxtropis falcate showed good anti - HBsAg activities (IC50 = 0.335mg/mL, SI >4; IC50< 21μg/mL, SI > 2.67); dalbergin (10) and 4′ - methoxy - quercetin - 3 -O - α - L - rhamnopyranosyl - (1→2) - β - D – glucopyranoside(13) from showed anti - HBsAg activities (IC50 = 45μg /mL, SI = 1.36; IC50>1.211 mg/mL, SI >1.121 ); (-) - pinocembrin (3), (-) - 7 - hydroxy - dihydroflavone (4), 4′ - methoxy - 2′ - hydroxy - chalcone (5) and dalbergin (10) from Oxtropis falcate showed weak anti - HSV-1 activities with MIC values of 74.4, 81.9, 82.0, 84.5, 85.0μg/mL; morusin (2) and mulberrofuran G (4) from Morus alba show anti - HSV-1 activities with MIC values of 7.74, 23.5,10.06μg/mL; morusin (2), cyclomorusin (3), mulberrofuran G (4), cylcomulberrin (5) showed good antimicrobial activities, among them, compounds 2 and 4 were more active than the positive medicine. Chapter 5 Review on active Anti - HBV natural compounds This review covers 67 literatures, outlined the anti - HBV methods in vitro and in vivo, summarized 77 anti - HBV natural compounds published between 1990 and 2007, including lignans and polyphenols, flavonoids, alkaloid and terpenoids.
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/224
Appears in Collections:昆明植物所硕博研究生毕业学位论文_学位论文

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轮叶棘豆、镰形棘豆、桑白皮化学成分及抗HBV、HSV-1生物活性研究.姚淑英[d].中国科学院昆明植物研究所,2007.20-25
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