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天山雪莲种子化学成分及其生物活性研究
MAIRA.SEIILGAZY
学位类型博士
导师阿吉艾克拜尔·艾萨
2017-06-03
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
关键词天山雪莲种子 化学成分 结构鉴定 生物活性
摘要

雪莲属于菊科凤毛菊属,主要分布于新疆境内的天山山脉、阿勒泰山脉和昆仑山脉,因此也称为天山雪莲,是中国常用的传统药。随着人们对它化学成分深入的研究,天山雪莲的功效也越来越得到重视并被广泛的应用于医药、食品和日用保健品等领域。与此同时,天山雪莲主要有效成分的提取及其综合利用技术也随之得到了发展,但对天山雪莲种子的化学成分尚未进行系统的研究。 本论文在前期文献调研过程中发现,雪莲种子的化学成分研究较少。因此本论文以雪莲种子的化学成分及其生物活性研究为主要目标,采用正相硅胶柱层析、反相硅胶ODS柱层析、葡聚糖凝胶Sephadex LH-20柱层析、MCI以及全自动纯化系统、半制备液相色谱等多种色谱分离手段,对雪莲种子的95%乙醇溶剂提取部位化学进行了系统分离纯化,分离得到25个化合物。运用UV、NMR、HR-ESI-MS等方法综合解析鉴定出其中22个化合物的结构。其中,化合物SIS-1被鉴定为新的倍半萜内酯并被命名为雪莲内酯D (1R*,3R*,5S*,6R*,7R*,8S*,11S*) -3,8-dihydroxyl-11,13-dihydrodehydrocostuslatone) 化合物 Pinoresinol-4ˊ-O-β-D- glucopyranoside A (SIS-9), 系统名为(2S,3S,4R,5R,6R) -6-(4-((1R,3S,3aR,6aS)-3- (4-hydroxy-3-methoxyphenyl)hexahydrofuro[3,4-c]furan-1-yl)-2-methoxyphenoxy)-5-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol) 被鉴定为新的木脂素。其余20个已知物被鉴定为deacylcynaropicirin (SIS-2), 8α-羟基-11β氢-11, 13-二氢去氢木香内酯 (SIS-3), 11β氢-11, 13-二氢去氢木香内酯8α-O-β-d-葡萄糖苷 (SIS-4), 牛蒡子苷 (SIS-5), 牛蒡子苷元 (SIS-6), matarasinol (SIS-7), matarasinoloside (SIS-8), 松脂醇-4ˊ-O-β-d-吡喃葡萄糖苷 (SIS-10), oleic acid (SIC-13), 香草精 (SIS-14), 3,5-二-O咖啡酰奎宁酸 (SIS-15), 苯甲酸(SIS-16), 1,3-二-O咖啡酰奎宁酸 (SIS-17), 3,5-二-O咖啡酰奎宁酯甲酸 (SIS-18), 芦丁 (SIS-19), β-腺苷 (SIS-20), 和绿原酸 (SIS-21), dihydrosyringin (SIS-22)。12个化合物包括2, 6, 9, 10, 11, 12, 13, 14, 15, 17, 18, 21和22 为雪莲中首次分离得到。对雪莲种子中分离得到的两个甾醇酯化合物sinkiangenorin A (SIS 11) and sinkiangenorin B (SIS 12) 测定了其对人肺癌细胞(A549)、人宫颈癌细胞 (Hela) 和 人乳腺癌细胞(MCF-7)的抑制活性。两个化合物均表现出一定的抑制活性。对雪莲种子分离得到的倍半萜类化合物(SIS 1–3) 测定了其对人前列腺癌细胞( PC-3)、人肺癌细胞 (A549) 和人宫颈癌细胞 (Hela)的细胞毒活性,三个化合物均对PC-3,Hela和A549细胞无细胞毒活性。

其他摘要

Saussurea involucrata belongs to the Asteraceae family mainly distributed in Tianshan mountain of Xinjiang, Russia, Kazakhstan, and Mongolia. Saussurea involucrata is widely used in pharmaceutical, food, health care products and other fields of its medicinal value. However, rare literature is available regarding the chemical composition of the seeds of S. involucrata.The main purpose of this dissertation is to isolate more biologically active compounds from seeds of S. involucrate from the 95% ethanol extract part. By using a variety of chromatographic techniques, such as silica gel, ODS, Sephadex LH-20, MCI open column and semi-preparative HPLC, 25 compounds were isolated, and the structures of 22 of them were identified. Among them, compound SIS-1 is a new guaianolide-type sesquiterpenoid lactone, named sausinlactone D, and compound SIS-9 is a new lignan, named pinoresinol-4ˊ-O-β-d-glucopyranoside A. The 20 known compounds were identified to be deacylcynaropicirin (SIS-2), 8α-hydroxyl-11βH-11,13-dihydrodehydrocostus lactone (SIS-3), and 11βH-11, 13-dihydrodehydro costuslactone 8α-O-β-d-glycoside (SIS-4), arctiin (SIS-5), arctigeniin (SIS-6), matarasinol (SIS-7), matarasinoloside (SIS-8), pinoresinol-4ˊ-O-β-d-glucopyranoside (SIS-10), oleic acid (SIS-13), vaniilic acid (SIS-14), 3,5-di-O-caffeoylquinic acid (SIS-15), benzonic acid (SIS-16), 1,3-di-O-caffeoylquinicacid (SIS-17), 3,5-di-O-caffeoyl quinic acid methyl ester (SIS-18), rutin (SIS-19), β-adenosine (SIS-20), and chlorogenic acids (SIS-21), dihydrosyringin (SIS-22).Thirteen compounds, via. 2, 6, 9, 10, 11, 12, 13, 14, 15, 17, 18, 21and 22, were isolated from S. involucrata for the first time. Moreover, two C21 steroidal esters compounds sinkiangenorin A (SIS-11) and sinkiangenorin B (SIS-12) were tested for their cytotoxicity against the cell lines of A549 (human lung carcinoma), MCF-7 (human breast adenocarcinoma cell line) and Hela (human cervix cancer), and both compounds showed inhibitory activity against the tested cell lines. Three sesquiterpenoid lactones, sausinlactone D (SIS-1), deacylcynaropicirin (SIS-2), and 8α-hydroxyl-11βH-11, 13-dihydrodehydrocostus lactone (SIS-3) were tested for their cytotoxicity against the tumor cell lines of A549 (human lung carcinoma), PC-3 (prostate cancer) and Hela (human cervix cancer), and all compounds were ineffective

文献类型学位论文
条目标识符http://ir.xjipc.cas.cn/handle/365002/4984
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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MAIRA.SEIILGAZY. 天山雪莲种子化学成分及其生物活性研究[D]. 北京. 中国科学院大学,2017.
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