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毛序准噶尔乌头的化学成分研究
外塔尼古丽·卡米力
学位类型博士
导师阿吉艾克拜尔·艾萨
2016-06-03
学位授予单位中国科学院大学
学位授予地点北京
学位专业有机化学
摘要

毛序准噶尔乌头 (Aconitum soongaricum var. Pubescens) 系毛茛科(Ranunculaceae) 乌头属 (Aconitum) 植物,是准噶尔乌头 (Aconitum soongaricum)的变种,主要分布于我国新疆、中亚地区,属中亚特有植物,《新疆植物志》记载,毛序准噶尔乌头有剧毒,可供药用,具有散风寒、除湿、止痛、治疗跌打损伤等功效,但是关于该植物的化学成分研究未见系统报道。 目前,国内对乌头属药用植物的研究主要集中在川乌、草乌、附子和雪上一枝蒿等常用中药上,而对新疆乌头属植物的研究较少。因此,本论文以中亚地区特有的毛序准噶尔乌头为研究对象,对其化学成分展开系统研究,旨在从中寻找结构新颖的活性化合物,为进一步的开发和利用新疆这一特有植物资源提供科学依据。 论文第一章对乌头属植物的分类,分布,化学成分及药用价值进行了系统的阐述,并对乌头属植物的特征化合物二萜类生物碱的分类和药理活性进行了简单描述。 第二章对广泛分布于新疆的毛序准噶尔乌头化学成分进行了系统研究: 1.化合物的分离及结构鉴定 对毛序准噶尔乌头中的化学成分进行了系统提取分离及纯化研究,共分离得到了21个单体化合物,并利用ESI-MS、IR、1D NMR和2D NMR等波谱技术鉴定了其结构。其中15个二萜生物碱化合物:pubsongorine A (1), pubsongorine B (2), 12-epi-napelline (3), senbusine A (bataconine) (4), 14-benzoyl-8-O- methylaconine (5), 12-epi-dehydronapelline (6), senbusine C (7) songorine (8), neoline (9), chasmanine (10), neojiangyouaconitine (11), benzoylaconine (12), 16, 17-dihydro-12β, 16β- epoxynapelline (13), songoramine(14), aconine (15);3个黄酮苷化合物: kaempferol-7-O-α-L-rhamnoside (16), kaempferol-3-O-β-D- glucopyranoside-7-O-α-L-rhamnoside(17), kaempferol-3-O-α-L-arabinopyranoside -7-O-α-L-rhamnoside (18); 1个肉桂酸: methyl 4-hydroxycinnamat (19); 1个苯酚: 4-Hydroxyphenyl-O-β-D-Glucopyranoside (20); 1个降倍半萜: (3S,5R,6R,7E,9S) -megastigman-7-en-3,5,6,9-tetraol (21)。化合物1和化合物2为新化合物,化合物4-6, 10-13, 15-21为首次从该植物中分离得到。 2. 单体化合物的细胞毒性筛选 用MTT比色法对分离得到的15个二萜生物碱化合物对MCF-7,HeLa,A549和PC-3四种肿瘤细胞株的细胞毒性进行了筛选。实验结果显示,这15个二萜生物碱化合物对MCF-7,HeLa,A549和PC-3细胞株表现出不同程度的细胞毒性。其中化合物2, 5, 9-15对PC-3细胞具有较好的细胞毒性,化合物1, 3-5, 9-13 和15对A549细胞具有较好的细胞毒性,化合物1, 3和15对HeLa细胞具有较好的细胞毒性,化合物1, 3, 5, 11和14对MCF-7细胞具有较好的细胞毒性,而其他化合物未表现出细胞毒性。 以上研究为从乌头属植物中进一步寻找高效低毒的单体化合物,探讨其药理活性提供了科学依据,丰富了乌头属植物的化学成分研究内容,为毛序准噶尔乌头的药理研究和进一步开发利用中亚这一特色植物资源奠定了基础。

其他摘要

Aconitum soongaricum var. Pubescens belonging to genus Aconitum (Ranunculaceae) plant, mainly distributed in the Xinjiang region of China and Central Asia. Aconitum soongaricum var. Pubescens is Uighur folk medicinal plant, used for for the treatment of cough, rheumatism, fracture and neuralgia. However, the system research of the chemical composition of the plant has not been reported. At present, domestic research on medicinal plants Aconitum focused on Aconitum carmichaelii,Aconitum kusnezoffii Reichb, Aconitum carmichaeli Debx and Aconitum racemulosum Franch which commonly used traditional Chinese medicine, but the system research of Xinjiang Aconitum is rare. In this dissertation, chemical composition from Aconitum soongaricum var. Pubescens which iswidely distributed in Central Asia has been studied, the aim was to provide some new and activity compounds for further scientific development and utilization of the unique resources in Central Asia. The first chapter, the classification, distribution, chemical composition and medicinal value of Aconitum plants were described. And then, the classification and pharmacological activity of diterpenoid alkaloids which were the characterized compounds of Aconitum were also described. The second chapter, phytochemical investigation on the chemical composition from A.soongaricum var.Pubescens was elaborated. 1. Isolation and identification of compounds Twenty-one compounds were identified by different spectrum methods, including Tow new diterpenoid alkaloids, pubsongorine A (1) and pubsongorine B (2), together with thirteen known diterpenoid alkaloids, 12-epi-napelline (3), senbusine A (bataconine) (4), 14-benzoyl-8-O-methylaconine (5), 12-epi-dehydronapelline (6), senbusineC(7) songorine (8), neoline (9), chasmanine (10), neojiangyouaconitine (11), benzoylaconine(12),16, 17-dihydro-12β, 16β- epoxynapelline (13), songoramine (14) and aconine (15), three flavonoid glycosides: kaempferol-7-O-α-L-rhamnoside (16), kaempferol-3-O-β-D-glucopyranoside-7-O-α-L-rhamnoside(17), and kaempferol-3- O-α-L-arabinopyranoside-7-O-α-L-rhamnoside (18), a cinnamic acid: methyl 4-hydroxycinnamat (19), a phenol: 4-Hydroxyphenyl-O-β-D-Glucopyranoside (20) and a drop sesquiterpene: (3S, 5R, 6R, 7E, 9S)-megastigman-7-en-3,5,6,9-tetraol (21) were isolated from A. soongaricum var.Pubescens. Compounds 4-6, 10-13, 15-21 were isolated from the plant for the first time. Their structures were established on the basis of spectroscopic analyses, including ESI-MS, IR and 1D and 2D NMR. 2. Screening monomeric cytotoxic compound Fifteen diterpenoid alkaloids were evaluated for their cytotoxic effects on the cancer cell lines MCF-7 (Human breast cancer cells), HeLa (Human cervical cancer cells), A549 (human lung adenocarcinoma cells) and PC-3 (prostate cancer cells) using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) method. The results of bioassays showed that compound 2, 5, 9-15 exhibited cytotoxicity activity against PC-3, Compound 1, 3-5, 9-13 and 15 exhibited cytotoxicity activity against A549, compound 1, 3 and 15 exhibited cytotoxicity activity against HeLa, Compound 1, 3, 5, 11 and 14 exhibited cytotoxicity activity against MCF-7. This study not only provided a scientific evidence for further research about screening high efficiency and low toxicity compounds from Aconitum, but also enriched the chemical constituents of A. soongaricum var. Pubescens, and established the foundation for the pharmacological research and further development and utilization of these endemic resources of medicinal plants in Central Asia.

文献类型学位论文
条目标识符http://ir.xjipc.cas.cn/handle/365002/4562
专题资源化学研究室
作者单位中国科学院新疆理化技术研究所
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外塔尼古丽·卡米力. 毛序准噶尔乌头的化学成分研究[D]. 北京. 中国科学院大学,2016.
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