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维吾尔医药用植物孜然化学成分及其生物活性筛选研究
谢喜国
学位类型硕士
导师阿布力米提·伊力
2011-06-03
学位授予单位中国科学院研究生院
学位授予地点北京
学位专业有机化学
关键词孜然 化学成分 脂肪酸合酶 活性
摘要孜然(Cuminum Cyminum L.)系伞形科(umbellifereae)孜然芹属植物,是我国新疆维吾尔医常用药材,用于治疗消化不良和胃寒腹痛等症。孜然果实粉末是维吾尔族、回族、克尔克孜族、哈萨克族等民族群众喜爱的调料,常用于烧烤肉食中,风味独特,是肉食品的上佳佐料。 脂肪酸合酶(FAS)广泛存在于动植物组织细胞中,是高等动物内源性脂肪酸合成的最重要的酶。研究发现FAS在肿瘤细胞和脂肪细胞中高表达,是治疗肥胖症和新的癌症化疗的潜在双重靶点。从天然产物中寻找、鉴定和提取脂肪酸合酶抑制剂越来越受到研究人员的重视。 目前国内外关于孜然的研究主要集中在孜然精油及其药理作用方面,文献多有报道孜然的生物活性,且都表现出较好的抗菌作用,对治疗某些疾病也有较好的疗效,而对于孜然中非精油成分的报道较少。由于没有关于孜然对脂肪酸合酶抑制活性的报道,结合孜然治疗消化系统疾病的良好功效,为阐明孜然的药用机理的物质基础,笔者以新疆和田产孜然为材料,以生物活性为指导,通过传统工艺,结合快速制备色谱技术,得到了一系列部位。通过脂肪酸合酶的抑制活性筛选实验,确定孜然对脂肪酸合酶抑制活性的有效部位及其最佳制备工艺。 通过生物活性筛选,确定了最佳提取溶剂为70%乙醇水溶液,继而对70%乙醇浸膏依次使用石油醚,二氯甲烷,乙酸乙酯,正丁醇进行萃取,对得到的4个部位进行脂肪酸合酶抑制活性实验,乙酸乙酯部位表现出了较高的抑制活性。选择乙酸乙酯部位为研究对象,用快速制备色谱技术,以氯仿甲醇系统为洗脱剂,得到7个部位,对其进行脂肪酸合酶抑制活性实验结果显示:氯仿洗脱部位和甲醇浓度4.9%的氯仿甲醇系统洗脱部位活性最好,IC50值分别为25.78 μg/mL和35.8 μg/mL。从以上两个部位中共分离得到11个化合物,鉴定了其中7个化合物的结构,分别为:豆甾醇 (I), 3β-乙酰氧基-12-齐墩果稀-11-酮 (II), 3β-乙酰氧基-16β-羟基-12-齐墩果稀-11-酮 (III), 5, 7, 4′-三羟基黄酮 (IV), 芹菜素-7-O-β-D-葡萄糖苷 (V), 胡萝卜苷 (VI),正三十醇 (VII), 7个化合物均为首次从该植物中获得。 为了扩大孜然资源的利用范围,我们以水蒸气蒸馏法从孜然种子中提取出精油,GC-MS进行检测,共鉴定了38个化合物,占总含量的98.55%,与文献对比后发现不同产地的相同植物,精油成分会有较大的差别;对孜然精油进行抗菌活性和抗氧化活性实验,结果表明孜然精油具有较好的生物活性,为开发相关产品提供了科学数据。
其他摘要Cuminum Cyminum L. belongs to the Umbelliferae family. The seeds of Cuminum Cyminum L. have been used for treatment of dyspepsia, diarrhoea in Uyghur traditional medicine and they also used as flavouring agents and spices. Fatty acid synthase (FAS) widely spread in the tissue cells of organisms, is a key enzyme that catalyzes the synthesis of endogenous long chain fatty acids. FAS has recently become an potential attractive and effective target for treating obesity and tumor for the expressing highly in the tumor cells and fatty cells. Bio-assay guided isolation and identification of fatty acid synthase inhibitors from nature products become more and more important. There are many studies on the essential oil and its biological activities of Cuminum Cyminum L. But the nonvolatile compound about Cuminum Cyminum L. was few reported especially in China. As the mechanism of inhibition of fatty acid synthase of Cuminum Cyminum L. has not been studied yet, it is essential to find out its material basis, and screening of the active extracts against fatty acid synthase. By means of tradition phytochemistry technology and modern Flash Chromatography, Cuminum Cyminum L. is preparation of different polar extracts and evaluation inhibiting capacities of fatty acid synthase. In our study, seven fatty acid synthase inhibitors were isolated from the 70% aqueous ethanolic extract of seeds of Cuminum Cyminum L. by activity-directed fractionation and purification processes. The ethanolic extract was first separated into petroleum ether, dichloromethane, ethyl acetate, n-butanol and water soluble fractions and screened for inhibitory activity against fatty acid synthase. The ethyl acetate fraction expresses the best capabilities of inhibition of fatty acid synthase. Further research of ethyl acetate fraction is of significance. It is divided into 7 fractions on the basis of different polar by Flash Chromatography. Eleven fatty acid synthase inhibitors, of which seven were identified, were isolated from the chloroform and the 4.9% (chloroform) methanol chloroform fractions, stigmasterol (I), 3β-acetoxy-12-oleanen-11-one (II), 3β-o-acetyl-16β-hydroxy-11-oxoolean-12-en (III), 5, 7, 4′-trihydroxyldihydroisoflavone (IV), apigenin-7-O-β-D-glucoside (V), daucosterol (VI), triacontanol (VII). Compounds I~VII were all obtained from Cuminum Cyminum L. for the first time. The essential oil was extracted from seeds of Cuminum Cyminum L. by steam distillation extraction method and the chemical compositions were analyzed by GC - MS. Forty-eight compounds were detected, of which 38 compounds that accounted for 98.53% of the total volatile oil were identified. The study of antibacterial activity and antioxidant properties prove that the essential oil shows powerful activity.
文献类型学位论文
条目标识符http://ir.xjipc.cas.cn/handle/365002/4437
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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谢喜国. 维吾尔医药用植物孜然化学成分及其生物活性筛选研究[D]. 北京. 中国科学院研究生院,2011.
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