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题名: 六种西部药用植物的化学成分及资源研究
作者: 许敏
学位类别: 博士
答辩日期: 2005-05-30
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: 杨崇仁
关键词: 药用植物资源 ; 坚龙胆 ; 红花龙胆 ; 麻花秦艽 ; 狭叶龙血树 ; 柬埔寨龙血树 ; 叶下珠 ; 化学分类 ; 抗真菌活性 ; 抗氧化活性 ; 抗酪氨酸酶活性 ; 抗乙酰胆碱酯酶活性
学位专业: 植物学
中文摘要: 药用植物资源的可持续发展是我国以传统中医药为特色的天然药物产业现代化的基础。通过系统的植物化学研究,应用多学科知识和技术手段对重要中药的种质资源进行评价,开发利用途径,将为可持续发展提供新的思路与方法。 本论文对具有西部地区特色的6种药用植物,坚龙胆(Gentiana rigescens Franch. ex. Hemsl.),红花龙胆(G. rhodantha Franch ex. Hemsl.),麻花秦艽(G. straminea Maxim),狭叶龙血树(Dracaena angustifolia Roxb),柬埔寨龙血树(D. cambodiana Pierre ex Gagnep)和叶下珠(Phyllanthus urinaria L.),开展了较系统的植物化学研究。其中,坚龙胆,麻花秦艽和叶下珠是我国药典收载的重要中药。本论文应用天然产物化学研究的方法,通过多种现代分离纯化手段,从上述6种植物中分离到146个化合物,应用高分辨质谱、1 D和2 D核磁共振谱,以及多种光谱和化学降解手段,鉴定了化学结构,其中48个为新化合物,化合物类型包括环烯醚萜甙,三萜及其甙,甾体及其甙,木脂素甙,黄酮及其甙,口山酮及其甙,水解单宁,简单酚类等多种类型的化合物。 在系统植物化学研究的基础上,本论文尝试扩展学科视野,应用多种技术手段对药用植物资源进行评价,开发适用的技术,为资源的可持续利用提供基础。 本论文共4章。 第一章对药典收载的坚龙胆、麻花秦艽以及云南民间药用植物红花龙胆的化学成分进行系统的研究,共分离鉴定了100个化合物,包括32个新化合物。其中6个为结构新颖的C-20位环合的达玛烷型三萜及其配糖体。 研究结果表明,这三种龙胆属药用植物的主要化学成分均以环烯醚萜甙类为主,并含有多种黄酮、口山酮类、简单酚性,以及三萜类化合物。许多成分常以配糖体的形式存在。龙胆属植物化学组的分子多样性对于该属植物的系统分类和新的天然生理活性物质的发现提供了条件,也为药用资源的合理利用提供了基础。 本研究结果进一步证明我国药典收载的中药龙胆和秦艽的基源植物的主要化学成分十分相似。两类中药材均以马钱子酸 (loganic acid)、龙胆苦甙(gentiopicroside), 獐芽菜甙(sweroside), 獐芽菜甙(swertiamarin)等裂环烯醚萜甙类化合物为其特征成分。这为它们相似的性味功能和治疗作用提供了化学的依据。 本研究发现,坚龙胆环烯醚萜甙类成分的分子组成与龙胆、条叶龙胆和三花龙胆仍有一定的差异,且坚龙胆具有特征性的达玛烷型三萜及其配糖体。同样,麻花秦艽虽与秦艽的主要成分相似,也仍然有明显的化学差异。虽然生理活性的比较研究尚有待于深入开展,化学上的差异提示,将不同的物种作为同一药材使用,不是明智的做法,尽管它们之间有相近的亲缘关系和类似的主要化学组成。我国药典的中药材质量标准向一名一物的方向发展,将会是必然的趋势。 本论文在化学研究的基础上,建立坚龙胆主要化学成分的高压液相色谱定量分析技术,进行指纹图谱的研究,对坚龙胆的药材品质与地理分布的关系做初步分析,并开发龙胆苦甙的工业化大量制备方法。为该中药资源的合理利用和相关中药产品的技术提升与开发提供技术基础。 本论文对分离到的酚性化合物进行抗酪氨酸酶活性和抗乙酰胆碱酯酶活性测试,发现红花龙胆中的口山酮类化合物具有抗乙酰胆碱酯酶活性。 本论文在系统化学研究的基础上,根据生源途径将龙胆属植物中的环烯醚萜甙类化合物分为4个结构类型,并按其存在的属下等级归为4类群,讨论龙胆属植物中环烯醚萜甙分子进化规律与系统发育的关系。研究结果提示:微籽组、匍茎组和叶萼组以含番木鳖甙类化合物为主,应为相对较原始的类群,且微籽组与匍茎组有更近的亲缘关系;秦艽组富含獐牙菜甙类型苦味成分,是龙胆属的进化类群,并与龙胆草组有更近的亲缘关系;鉴于红花龙胆以富含半缩醛类型和番木鳖型的环烯醚萜甙类成分为特征,在环烯醚萜甙分子进化中具有特殊的地位,并富含口山酮类和苯并酮类成分,支持把红花龙胆所属的类群从龙胆属中独立出来,成立狭蕊龙胆属的观点。以上植物化学分类学研究结果与经典分类学和分支分类提出的龙胆属部分属下系统分类观点相一致。 第二章对狭叶龙血树和柬埔寨龙血树较系统的植物化学研究,分离到31个化学成分,其中16个为新的甾体化合物。 本论文通过对甾体成分组成的比较,讨论狭叶龙血树和柬埔寨龙血树与剑叶龙血树(D. cochinchinensis) 之间的分类学关系。鉴于柬埔寨龙血树与剑叶龙血树的化学组成十分相似,但是剑叶龙血树化学多样性较柬埔寨龙血树丰富,且二者形态有明显差异,提出二者可能是近缘物种,但是不是同一物种的观点。这也为剑叶龙血树产生的树脂作为龙血竭使用,但是柬埔寨龙血树不产脂或产脂极少的观点提供了科学依据。狭叶龙血树以富含磺酰基甾体成分为主,与剑叶龙血树有显著的区别,应是独立的种。 本论文还对分离到的甾体化合物进行了抗真菌活性测定,结果表明,C-1位的配糖链为-O-鼠李吡喃糖基(1→2)阿拉伯吡喃糖基的螺甾烷配糖体对新型隐球菌显示有一定的抗真菌活性。 第三章对西双版纳产的叶下珠进行化学研究,分离鉴定15个化学成分。发现水解单宁类化合物为叶下珠的主要成分。 本论文在植物化学研究的基础上,制备指标成分鞣料云实素的标准对照品,建立HPLC定量分析方法,对叶下珠药材的现行质量标准进行修订,同时,开发主要活性物质鞣料云实素的大量制备技术,为叶下珠资源的合理利用以及叶下珠产品的二次开发提供技术基础。 本论文对分离到的酚类成分进行DPPH自由基清除活性与酪氨酸酶抑制活性的测试,并讨论化学结构与活性的关系。试验结果表明,叶下珠全株及其主要酚类化合物均具有显著的抗氧化活性。分离到的所有化合物对酪氨酸酶均有一定抑制作用。其中,鞣花单宁类化合物的活性最为显著。酚类化合物的上述活性不仅与羟基的数量有关,也与酚类的母核结构有一定关系。 最后,本论文第四章对龙胆属植物的药用植物资源及其生物活性进行文献综述。 以上研究结果,已发表论文3篇,一篇为SCI论文,SCI期刊接收发表论文2篇,待发表文章6篇。申请专利2项。
英文摘要: In China the modernization of Traditional Chinese Medicine is based on the research of the sustainable development of medical plants resources. The phytochemical investigation on medicinal plants will provide strong support for promotion of the sustainable development by means of modern scientific technology. This thesis focuses on not only the discovery of new natural compounds from six medicinal plants in west China (Gentiana rigescens Franch ex. Hemsl., G. rhodantha Franch ex. Hemsl., G. straminea Maxim, Phyllanthus urinaria, Dracaena argustifolia and D. cambodiana), but also the resources investigation of these plants. 146 compounds, including iridoidal glycosides, xanthones, flavonoids and phenolic glycosides, as well as triterpenoid and steroidal saponins, have been purified and identified. Among of them, there are 48 new compounds. Bioactive assay showed that some triterpenoids and steroids have antifungal activity, while phenolic glycosides displayed inhibitory activity on tyrosinase and acetylcholinesterase. Moreover, the thesis established HPLC analytical methods for quality control of two medicinal plants, Gentiana rigescens and Phyllanthus urinaria. The methods for large scale isolation and purification of gentiopicroside and corilagin from plants were also invented. The thesis consists of the following four chapters. Chapter 1. As a part of our research on Gentianaceous medicinal plant, three species from genus Gentiana, G. rigescens, G. rhodantha, and G. straminea, were systematically studied, which led to the isolation of 100 compounds. Among of them, there are 32 new compounds, including six new 20S,25-epoxy dammarane triterpenoids. A possible biogenetic pathway of the isolated iridoidal compounds, the major components in G. rigenses was proposed. In addition, a rapid, sensitive and selective quantitative analytical method was established by HPLC, for the analysis of loganic acid, swertiamarin, gentiopicroside, sweroside and 2'-(o,m-dihydroxybenzoyl)-sweroside, the five major bioactive compounds in roots of G. rigescens. It can be readily utilized as a suitable method for the quality control of G. rigescens. Moreover, a method for large scale isolation and purification of gentiopicroside from Gentiana spp. was invented, which is low-cost and suitable for industrial use. The above research results showed the significance of molecular diversity in genus Gentiana for not only the discovery of new bioactive natural products, but also the sustainable ultilization of its plant resources. The phylogeny of genus Gentiana was discussed on the basis of the biosynthetic pathway of iridoid glucosides, the major components in this genus. And, the rules of accumulation and distribution of the secondary metabolites in the plants and its significance for chemotaxonomy is discussed. Chapter 2. Liliales that contains steroidal glycosides as main constituents is an important group in Monocotyledons. Many of them are important medicinal plants. In order to further investigate the molecular diversity of natural steroids and to discover bioactive products, 2 species (Dacaena angustifolia and D. cambodiana) were studied. 31 compounds was isolated and identified, including 16 new compounds. Antifungal test showed that some of the isolated steroids had inhibitory activity on Cryptococcus neoformans. Chapter 3. A detailed phytochemical investigation on Phyllanthus urinaria was carried out, which led to the isolation of 15 phenolic compounds (1-15). Among them the structure of repandinin B (1) is represented by total assignment of NMR data. With the examination of the DPPH assay and inhibitory activity on tyrosinase, most of the isolated compounds showed stronger antioxidant activity than that of the positive control. In addition, a HPLC fingerprint analysis method was established and used in the analysis of the P. urinaria. A quantitative study of this herb was concluded. A new method for large scale isolation and purification of corilagin from plant resources was invented, which was low-cost and suitable for industrial use. Based on this study, a new standard of P. urinaria was proposed. Chapter 4. Review The advances including the medicinal plant resources and biological activities of genus Gentiana were reviewed. Based on above research work, three papers have been published, two papers have been accepted, one paper has been submitted, and another six are in preparation. Moreover, two patents were published.
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/288
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六种西部药用植物的化学成分及资源研究.许敏[d].中国科学院昆明植物研究所,2005.20-25
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