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STUDY ON CHEMICAL COMPOSITION AND BIOLOGICAL ACTIVITY OF TWO SPECIES OF THE GENUS DRACOCEPHALUM
Alternative Title两种青兰属植物化学成分及其生物活性研究
Zokir Omonovich Toshmatov
Subtype博士
Thesis Advisor阿吉艾克拜尔·艾萨
2018-06-02
Degree Grantor中国科学院大学
Place of Conferral北京
Degree Discipline有机化学
KeywordDracocephalum Moldavica Dracocephalum Komarovii Chemical Components Structural Elucidation Bioactivity
Abstract
唇形科植物包含约220属3500种分布于全球,其中在地中海地区和亚洲最为广泛,在中国有96属807种植物分布。青兰属包括70种植物,其中有35种分布于中国,9种分布于乌兹别克斯坦。青兰属植物被广泛应用于传统医药治疗胃溃疡、喉炎、头痛、急性呼吸系统感染、腹泻和类风湿性关节炎。至目前,关于青兰属植物Dracocephalum komarovii 和D. moldavica的化学成分及其生物后活性研究还较少。本文利用各种色谱分离技术包括硅胶柱层析、凝胶柱层析和半制备型高效液相色谱,从D. komarovii 的70%乙醇提取物和D. moldavica的95%的乙醇提取物中分别分离得到29和12个化合物。这些化合物的结构通过质谱/核磁共振等波谱数据分析和与报道数据的对比得以确认。从D. komarovii中分离的29个化合物包括三个新的单萜苷类化合物komarovin A(Dr.k-17), komarovin B(Dr.k-26) 和komarovin C(Dr.k-27)和26个已知物。这些已知物的结构被鉴定为藿香黄酮醇(Dr.k-1),芫花素(Dr.k-2),熊竹素(Dr.k-3),β-谷甾醇(Dr.k-4),豆甾醇(Dr.k-5),4¢,5-二羟基-3,6,7-三甲氧基黄酮(Dr.k-6),黄姜味草醇(Dr.k-7),卡来可黄素(Dr.k-8),芹菜素(Dr.k-9),木犀草素(Dr.k-10),槲皮素-3,4'-二甲醚(Dr.k-11),蓟黄素(Dr.k-12),金圣草黄素(Dr.k-13),香叶木素(Dr.k-14),甲基条叶蓟素(Dr.k-15),柠檬烯-10-醇 10-O-β-d-吡喃葡萄糖基-(1→2)-β-d-吡喃葡萄糖苷(Dr.k-16),山奈酚-3-甲基醚(Dr.k-18),木犀草素-7- O-β-甲基葡萄糖苷酸(Dr.k-19),芹菜素-7-葡萄糖苷(Dr.k-20),木犀草素-7-葡萄糖苷(Dr.k-21),oresbiusin B (Dr.k-22),金合欢素-7-葡萄糖苷(Dr.k-23),木犀草素-7-葡萄糖苷酸(Dr.k-24),金合欢素-7-O-[α-l-鼠李糖基-(1→6)]-β-d-吡喃葡萄糖苷(Dr.k-25),邻苯二甲酸正丁酯(Dr.k-28),和alphitol(Dr.k-29)。以上化合物均是首次从D. komarovii被分离得到。从D. moldavica中分离得到12个化合物,其中8个化合物被鉴定为迷迭香酸甲酯(Dr.m-1),落叶松树脂醇-4¢-O-β-d-葡萄糖苷(Dr.m-2),oresbiusin B(Dr.k-22),针枞酚(Dr.m-4),栀子色素B(Dr.m-5),芹菜素(Dr.m-9),木樨草素(Dr.k-10),芹菜素-7-O-β-甲基葡萄糖醛酸苷 (Dr.m-8),其余4个化合物的结构解析正在进行当中。其中,落叶松树脂醇-4¢-O-β-d-葡萄糖苷(Dr.m-2),oresbiusin B(Dr.k-22)和针枞酚(Dr.m-4)是首次从D. moldavica被发现。6个化合物:芫花素(Dr.k-2),熊竹素(Dr.k-3),槲皮素-3,4'-二甲醚(Dr.k-12),金圣草黄素(Dr.k-14),甲基条叶蓟素(Dr.k-16)和山奈酚-3-甲基醚(Dr.k-17)是从青兰属植物中首次发现。此外,对7个黄酮苷类化合物Dr.k-2,3,6,7,9,11和12进行了肌力作用、血管舒张和解痉作用的活性研究,发现这7个化合物均表现出一定活性。对三个单萜苷类化合物,柠檬烯-10-醇 10-O-β-d-吡喃葡萄糖基-(1→2)-β-d-吡喃葡萄糖苷(Dr.k-16),komarovin B (Dr.k-26)和komarovin C (Dr.k-27)进行了抗炎活性研究,发现其均具有较好的抗炎活性。
Other Abstract
Plants of the family Lamiaceae containing approximately 3500 species in 220 genera are distributed worldwide, but mostly in the Mediterranean region and Asia. China has 807 species in 96 genera. There are 70 species of genus Dracocephalum, among them, 35 species are distributed in China and 9 species in Uzbekistan. Plants of the genus Dracocephalum are used in folk medicine. The aerial parts are widely used for the treatment of gastric ulcers, laryngitis, headache, acute respiratory infection, diarrhea and rheumatoid arthritis. However, rare literature is available regarding to the chemical composition of the D. komarovii and D. moldavicaThe purpose of this dissertation is to isolate more biologically active compounds from 70% ethanol extract part of D. komarovii and from the 95% ethanol extract part of D. moldavica. By using a variety of chromatographic techniques, such as silica gel, ODS, Sephadex LH-20 open column and semi-preparative HPLC 29 compounds were isolated from D. komarovii and 12 compounds were isolated from D. moldavica. Their structures were identified on the basis of spectroscopic data analysis including mass and NMR and comparison with the reported data. The two compounds of them were isolated as a mixture, but identified on the basis of their NMR data and mass data, together with comparison with literatures. Among them, compounds Dr.k-17, Dr.k-26 and Dr.k-27 are new monoterpene glycosides from D. komarovii, named komarovins A, B and C. The 29 known compounds from D. komarovii were identified to be pachypodol (Dr.k-1), genkwanin (Dr.k-2), kumatakenin (Dr.k-3), β-sitosterol (Dr.k-4), stigmasterol (Dr.k-5), penduletin (Dr.k-6), xanthomicrol (Dr.k-7), calycopterin (Dr.k-8), apigenin (Dr.k-9), luteolin (Dr.k-10), quercetin 3,4'-dimethyl ether (Dr.k-11), cirsimaritin (Dr.k-12), chrysoeriol (Dr.k-13), diosmetin (Dr.k-14), cirsilineol (Dr.k-15), limonen-10-ol 10-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (Dr.k-16), kaempferol 3-methyl ether (Dr.k-18), luteolin-7-O-β-methylglucuronide (Dr.k-19), apigenin-7-O-glucoside (Dr.k-20), luteolin-7-O-glucoside (Dr.k-21), oresbiusin B (Dr.k-22), acacetin-7-O-glucoside (Dr.k-23), luteolin-7-O-glucuronide (Dr.k-24), acacetin-7-O-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside (Dr.k-25), dibutylphthalate (Dr.k-28), alphitol (Dr.k-29). 12 compounds were isolated from D. moldavica, and eight of them were identified to be methyl rosmarinate (Dr.m-1), lariciresinol-4¢-O-β-d-glucoside (Dr.m-2), oresbiusin B (Dr.k-22), piceol (Dr.m-4), gardenin B (Dr.m-5), apigenin (Dr.k-9), luteolin (Dr.k-10), apigenin-7-O-β-methylglucuronide (Dr.m-8), the structures elucidation of other four compounds, is ongoing. All compounds were isolated from D. komarovii for the first time and the compounds Dr.m-2, Dr.k-22, Dr.m-4 were isolated from D. moldavica for the first time. Six compounds, quercetin 3,4'-dimethyl ether, genkwanin, kumatakenin, chrysoeriol, cirsilineol, kaempferol 3-methyl ether from D. komarovii and two compounds from D. moldavica Dr.m-2, Dr.m-4, were isolated from the Dracocephalum genus for the first time. Moreover, seven aglycon flavons compounds genkwanin (Dr.k-2), kumatakenin (Dr.k-3), penduletin (Dr.k-6), xanthomicrol (Dr.k-7), apigenin (Dr.k-9), quercetin 3,4'-dimethyl ether (Dr.k-11), and cirsimaritin (Dr.k-12) were tested for their inotropic, vasorelaxant and spasmolytic effects, and all compounds showed inotropic, vasorelaxant and spasmolytic activity. Three monoterpen glycosides, limonen-10-ol 10-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (Dr.k-16), komarovin B (Dr.k-26) and komarovin C (Dr.k-27) were tested for their anti-inflammatory activity, and all of them showed anti-inflammatory activity。
Pages139
Document Type学位论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5466
Collection资源化学研究室
Recommended Citation
GB/T 7714
Zokir Omonovich Toshmatov. STUDY ON CHEMICAL COMPOSITION AND BIOLOGICAL ACTIVITY OF TWO SPECIES OF THE GENUS DRACOCEPHALUM[D]. 北京. 中国科学院大学,2018.
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