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罗布麻和雪菊的化学成分及其生物活性研究
NURMIRZA BEGMATOV
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
关键词罗布麻 雪菊 分离纯化 结构鉴定 黄酮 查尔酮 生物活性筛选和评价
摘要

本论文对两种来源于中国新疆的两种药用植物——罗布麻(Apocynum lancifolium)和雪菊(Coreopsis tinctoria)花中的化学成分及其生物活性进行了研究。通过提取、萃取、柱层析和高效液相色谱等多种分离纯化方法,从罗布麻(A. lancifolium)中分离得到22个单体化合物,从雪菊(C. tinctoria)中得到23个化合物,其中三个为新化合物。利用质谱、核磁共振波谱、单晶X-射线衍射、紫外和红外光谱等手段确定了上述单体化合物的结构。从罗布麻(A.lancifolium)中获得的化合物被鉴定为:菜油甾醇 (AL-1),羽扇豆醇(AL-2), β-谷甾醇 (AL-3), 对羟基苯甲酸 (AL-4), 3, 4-二羟基苯甲酸甲酯(AL-5), 伞形花内酯 (AL-6),七叶亭 (AL-7), β-谷甾醇-d-吡喃葡萄糖苷 (AL-8), 山奈酚 (AL-9), 槲皮素 (AL-10), 黄芪苷 (AL-11), 异槲皮苷 (AL-12), 金丝桃苷 (AL-13), 烟花苷(AL-14), 咖啡酸(AL-15), 原儿茶酸 (AL-16), 1-(3,4-二羟基肉桂酰)-环戊烷-2′,3′-二醇 (AL-17), l-甲基肌醇 (AL-18), 三叶豆苷 (AL-19), 芦丁 (AL-20), 槲皮素-3-O-β-d-半乳糖苷-(1→6)-O-α-l-鼠李糖 (AL-21), 槲皮素-3-O-β-d-半乳糖醛酸苷 (AL-22)。从雪菊(C. tinctoria)中得到的化合物被鉴定为:圣草酚 (CT-1), 3′, 4′, 7-三羟基黄酮 (CT-2), 3′,4′,7,8-四羟基黄酮烷(CT-3), 紫杉叶素 (CT-4), 紫铆素 (CT-5), 紫铆花素 (CT-6), 木犀草素 (CT-7), 槲皮素 (CT-8), 3-(3,4-二羟基苯)-1-(2,3,4-三羟基苯)-2-羟丙基-2-烯-1-酮 (CT-9), 金鸡菊查尔酮 (CT-10),金鸡菊查尔酮 3′-(3,4-二羟基苯酰胺)-7-酮(CT-11), 8, 3′, 4′-三羟基黄酮-7-O-β-d-吡喃葡萄糖苷 (CT-12), 金鸡菊查尔酮-4′-O-葡萄糖苷 (CT-13), 异奥卡宁-7-O-β-d-葡萄糖苷 (CT-14), 六氢黄酮-7-O-β-d-葡萄糖苷 (CT-15), 槲皮素-7-O-β-d-葡萄糖苷(CT-16), 环己六醇 (CT-17), 1-二十六烷醇(CT-18), 十八烷酸(CT-19), β-香树脂醇 (CT-20),豆甾醇葡萄糖苷 (CT-21) 2-丙烯酸,3-(3-羟基-4-甲氧苯基),甲基脂 CT-23. 对化合物CT-10进行甲基化后得到一个新化合物3′,4′-三甲氧基-金鸡菊查尔酮(CT-22)。化合物AL-1, AL-14, 和AL-17是首次从罗布麻属植物中被发现,化合物AL-1, AL-7, AL-14, AL-17, AL-18和AL-22是首次从罗布麻中分离得到。从雪菊中分离得到的化合物CT-9, CT-11和CT-22为新化合物,化合物CT-1, CT-2, CT-3, CT-5, CT-12, CT-17和CT-21为该植物中首次发现。通过HPLC分析对植物中的主要成分进行了定量分析。在对HPLC分析条件进行优化后,找到了罗布麻和雪菊提取物的最佳分析条件(见实验部分HPLC方法2)。在该分析条件下,山奈酚、槲皮素、黄芪苷、三叶豆苷、烟花苷、紫铆花素、金鸡菊查尔酮和马里苷等化合物获得了较好的分离。由于罗布麻和雪菊具有广泛的生物活性,所以对所获得的化合物和流份进行了一系列活性测试,如针对DPPH的抗自由基活性,针对酪氨酸磷酸酶1B的降糖活性,针对金黄色葡萄球菌S. aureus (ATCC 6538)、大肠杆菌E. coli (ATCC 11229)和白色念珠菌C. albicans (ATCC 10231)等细菌和病原体的抗菌活性测试,针对小鼠B16黑素瘤细胞的抗白癜风活性,针对人乳腺癌细胞株MCF-7、宫颈癌细胞株、前列腺癌细胞PC-3和人肺泡基底上皮细胞A549的抗癌活性测试。其中,结果显示,这些化合物和流份具有良好的抗氧化、降糖、抗癌和抗白癜风活性。此外,该论文还尝试了对植物中的总黄酮进行富集和纯化。通过单因素和正交实验,发现用70%的乙醇进行提取,然后大孔树脂HPD-300进行富集可获得最高产率的总黄酮。

其他摘要

ABSTRACTChemical studies of secondary metabolites of the 70% EtOH extracts of the flowers of Apocynum lancifolium and Coreopsis tinctoria delivered in the isolation of 22 and 23 individual compounds, respectively, including flavonoids, phenolic acids and chalcones via various chromatographic methods and preparative HPLC. Three new biological active compounds, (3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)-2-hydroxyprop-2-en-1-one (CT-9), okanin-3′-(3″,4″-dihydroxybenzamide) (CT-11) and 4,3′,4′-trimethoxy-okanin (CT-22), belonging to natural class of chalcones were found from the flowers C. tinctoria under column chromatography method. The structures of isolated compounds were elucidated on the basis of spectroscopic analysis including 1D and 2D NMR, ESI-MS spectroscopy and X-ray crystallography. Compounds from A. lancifolium were identified as: ergost-5-en-3-ol (AL-1), lupeol (AL-2), β-sitosterol (AL-3), p-hydroxybenzoic acid (AL-4), 3,4-dihydroxybenzoic acid methyl ester (AL-5), umbelliferon (AL-6), esculetin (AL-7), β-sitosterol-d-glucopyranoside (AL-8), kaempferol (AL-9), quercetin (AL-10), astragalin (AL-11), isoquercitrin (AL-12), hyperoside (AL-13), nicotiflorin (AL-14), caffeic acid (AL-15), protocatechoic acid (AL-16), 1-(3,4-dihydroxycinnamoyl)-cyclopentane-2′,3′-diol (AL-17), l-bornesitol (AL-18), trifolin (AL-19), rutin (AL-20), quercetin-3-O-β-d-galactoside-(1→6)-O-α-l-rhamnose (AL-21), quercetin-3-O-β-d-galacturonide (AL-22). Individual compounds obtained from C. tinctoria were elucidated as: eriodictyol (CT-1), 3′, 4′, 7-trihydroxyflavone (CT-2), 3′, 4′, 7, 8-tetrahydroxyflavanone (CT-3), taxifolin (CT-4), butin (CT-5), butein (CT-6), luteolin (CT-7), quercetin (CT-8), 3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)-2-hydroxyprop-2-en-1-one (CT-9), okanin (CT-10), okanin-3′-(3″,4″-dihydroxybenzamide) (CT-11), 8, 3′, 4′-trihydroxyflavone-7-O-β-d-glucopyranoside (CT-12), okanin-4′-O-glucoside (CT-13), isookanin-7-O-β-d-glucoside (CT-14), quercetagetin-7-O-β-d-glucoside (CT-15), quercetin-7-O-β-d-glucoside (CT-16), myo-inositol (CT-17), 1-hexacosanol (CT-18), octadecanoic acid (CT-19), β-amyrin (CT-20), stigmasterol glucoside (CT-21). Methylation of compound (CT-10) generateda new compound 4,3′,4′-trimethoxy-okanin (CT-22) and a known one, 2-propenoic acid, 3-(3-hydroxy-4-methoxyphenyl), methyl ester (CT-23). 4,3¢,4¢-trimethoxy-okanin (CT-22) after methylation was resulted as a new biological resource. Compounds AL-1, AL-14, and AL-17 were isolated from the genus Apocynum and AL-1, AL-7, AL-14, AL-17, AL-18 and AL-22 were isolated from A. lancifolium for the first time. Additionally, compounds CT-1, CT-2, CT-3, CT-5, CT-12, CT-17, 3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)-2-hydroxyprop-2-en-1-one, okanin-3′-(3″,4″-dihydroxybenzamide), CT-21, 2-propenoic acid, 3-(3-hydroxy-4-methoxyphenyl), methyl ester CT-23 were identified from the genus and species of C. tinctoria for the first time. HPLC analysis for quantification of some major flavonoids and chalcones was performed. Under the optimized HPLC conditions mentioned in experimental section, best separation of A. lancifolium and C. tinctoria extracts were obtained in 90 min with method 2, Waters sunfire C18 column 4.6×250mm, 5 μm, delivered by acetonitrile/methanol/ 0.2% formic acid in water and detection at 210, 254 and 360 nm. This condition yielded critical separation for kempferol, quercetin, astragalin, trifolin, hyperoside, nicotiflorin, butein, 3-(3, 4-dihydroxyphenyl)-1-(2, 3, 4-trihydroxyphenyl)-2-hydroxyprop-2-en-1-one, okanin and marein.A. lancifolium and C. tinctoria are wildly used in traditional Uighur medicine for the treatment of hypertension, diabetic and hypolipidaemia. In this study, the pharmacological effects including free radical scavenging activity by using DPPH, antidiabetic effects against Protein Tyrosine Phosphatase 1B (PTP-1B), antimicrobial activities against bacterial and fungal pathogens such as S. aureus (ATCC 6538), E. coli (ATCC 11229) and C. albicans (ATCC 10231), anti-vitiligo activity against B16 cell, and anti-cancer activities against breast cells MCF-7, the cervical cancer cells Hela, the prostate cancer PC-3 and the adenocarcinomic human alveolar basal epithelial cells A549, of obtained individual compounds and bioactive fractions were tested. Results indicated that the isolated compounds and bioactive crude extracts delivered promising antioxidation, antidiabetic, antitumor and antivitiligo activities.Separation and purification of the total flavonoids using various macroporous resins was also attempted. Under optimized static adsorption-desorption process obtained by single factor and orthogonal array design methods, HPD-300 macroporous resin gave the most amount of total flavonoids from the 70% EtOH extract of the flowers of the investigated plants.

文献类型学位论文
条目标识符http://ir.xjipc.cas.cn/handle/365002/4868
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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NURMIRZA BEGMATOV. 罗布麻和雪菊的化学成分及其生物活性研究[D]. 北京. 中国科学院大学,2016.
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