摘要
多茎委陵菜(Potentilla multicaulis Bunge)属于蔷薇科(Rosaceae)委陵菜属植物。委陵菜属广泛分布于北温带,大部分为多年生草本,全球有500余种,我国有86种,全国各省均有分布,具有较好的抗旱、抗寒性能。有些种类的根部富含淀粉,可供食用和酿酒,可以用作草坪或荒坡绿化的材料,并可药用,其中的药用植物有20多个种和变种。它们或鲜花或全草或根部入药,多具清热、解毒、消肿、行气之功效。
箭叶橐吾(Ligularia sagitta mattf)为菊科菊科(Compositae)橐吾属植物,多年生草本,高40～80厘米,分布于甘肃、内蒙古、陕西、青海、四川西部,生于海拔1100-3700米的河滩、山麓、林缘、林下及灌丛。箭叶橐吾具有催吐的功能,在民间用于止咳、平喘、消炎止痛、理气活血、解毒消肿,及治疗跌打损伤等。藏药中可用于治疗四肢强直或挛急、跛跷、疖痛、炭瘟、新旧疮疡各种皮肤病、女产后病、肌骨黄水充斥等,特别对类风湿性关节炎的治疗效果甚佳。
狭叶牡蒿(Artemisia angustissima Nakai)属于菊科(Compositae)春黄菊族(Anthemideae)蒿属多年生草本。蒿属全世界约300余种。我国有186种,44变种,分布遍及全国各地,为我国种子植物中少有的大属,且为民族民间广泛使用的一大类药物,本属植物中的黄花蒿(A.annua L),青蒿(A.apiacea Hance),茵陈蒿(A.capillaris Thunb)和艾(A.argyi Levl.et Vant.)等均入药,尤以艾的用途最广,黄花蒿可治疟疾,还可制酒饼,并为中国药典收载品种,青蒿素类药物是目前疗效最迅速的抗疟药物。因此,蒿属植物的研究和应用有深远的意义和价值。
本文对以上3种植物(Potentilla multicaulis Bunge(根部),Ligularia sagittamattf(全草),和Artemisia angustissima Nakai(全草))做了有关化学成分和生物活性的研究,采用常规的柱层析(CC)、制备薄层层析(PTLC)、重结晶和化学转化等手段对其中的化学成份进行了分离,利用UV,IR,EI-MS,FAB-MS,HR-MS,~1H NMR,~(13)C NMR,DEPT,~1H-~1H COSY,NOEDS,HSQC,HMBC,~1H-~1H NOESY,X-ray单晶衍射等现代波谱技术确定了其中包括单萜、倍半萜、三萜、谷甾醇、胡萝卜甙、黄酮、苯的衍生物及其苷等多个类型的87个化合物的结构,其中有23个为新化合物,包括从Potentilla multicaulis Bunge(根部)分离得到的2个骨架新颖的蒲公英烷型三萜以及从Ligularia sagitta mattf(全草)得到的2个具有新骨架的倍半萜衍生物和2个新颖的倍半萜衍生物二聚体。我们还对其中部分化合物采用SRB法测试了对人体早幼粒白血病细胞(human promyelocyticleukemia,HL-60 cells),人肝癌细胞(human hepatoma,,SMMC-7721 cells)和人宫颈癌细胞(human cervical carcinoma,HeLa cells)的抑制活性,发现化合物P2b对HL-60具有弱细胞毒活性,L8a对HL-60和SMMC-7721具有中等细胞毒活性,L16和L17对HL-60具有弱细胞毒活性。
最后本文对近10年来见诸报道的四环三萜化合物作了扼要介绍。
本论文可望为从天然植物中寻找活性成分,并以此研究构效关系,以及进一步了解生态环境对植物化学成分的影响,研究植物化学分类学等方面提供科学依据。
More than 200 species of Potentilla plants are distributed throughout the world, and about 90 species are widespread in China. Some species of them have long been used as traditional Chinese medicinal herbs as antirheumatic, for detoxification, and curing dysentery and scabies. The characteristic components of this genus are triterpenoids and tannins. The constituents of Potentilla multicaulis had not been found to be reported about its constituents.
The genus Ligularia has been taxonomically placed in the Compositae with ca. 100 species distributed within China, more than 20 species have long been used for folk medicines. Their roots, stems, leaves, and flowers possess efficacies of antipyretic, relieving phlegm and cough, invigorating circulation of blood, and soothing pain. The main components of them are eremophilane sesquiterpenes and pyrrolizidine alkaloids with strong physiological actvities. In our long-standing interest in the study of biodiversity and searching for bioactive compounds from several Ligularia species, those results showed that the components from the same genus, even from the same species, displayed a remarkable difference because of the differences of ecological environments and collection seasons. The constitutes study of the plant Ligularia sagitta mattf would show us the relations between chemical constituents and ecology circumstance.
The plant Artemisia angustissima Nakai is the genus Artemisia of the family Compositae. More than 300 species were found widely in the world. About 186 species are distributed in China, mainly distributed in the north area. Some species of them such as A.annua L,A. apiacea Hance,A capillaris Thunb, and A.argyi Levl. et Vant. are used as traditional Chinese medicinal herbs. So it will be significative to study the plants of the genus Artemisia.
In this thesis we studied the chemical constituents of the three plants mentioned above. The chemical constituents of 82 compounds were isolated by means of silica gel column chromatography (CC), preparative layer chromatography (PTLC), recrystallization and chemical transformatione etc. 23 compounds of them were new, including 2 new triterpanoids with novel taraxerane skeleton, 2 new sesquiterpenes with new carbon skeleton, and 2 new novel dimeric sesquiterpenes. The structures of these compounds were elucidated by spectroscopic methods: UV, IR, EI-MS, FAB-MS, HR-MS, ~1H NMR, ~(13)C NMR, DEPT, NOEDS, ~1H-~1H COSY, HSQC, HMBC, ~1H-~1H NOESY, and X-ray crystallography.
Furthermore the bioactivities of some compounds were studied, using SRB method to test their cytotoxic activities against human promyelocytic leukemia (HL-60) cells, human hepatoma (SMMC-7721) cells, and human cervical carcinoma (HeLa) cells. Compound P2b exhibited weak cytotoxic activity against HL-60 cells, L8a exhibited moderate cytotoxic activity against HL-60 and SMMC-7721 cells, and compounds L16 and L17 showed weak cytotoxic activity against HL-60 cells.
Finally, tetracyclic triterpenoids from natural products reported from 1997 to 2007 were reviewed in this thesis.
This thesis would be a helpful reference for the research of biodiversity and searching for bioactive compounds from natural products, as well as chemotaxonomy and the relationship between structure and bioactivity effect.
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