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研究生:劉美珍
研究生(外文):Meei-Jen Liou
論文名稱:小紅參、大理茜草、大葉樹蘭及降真香之成分研究
論文名稱(外文):Studies on the Constituents of Rubia yunnanensis, R. ustulata, Aglaia elliptifolia and Acronychia pedunculata
指導教授:吳天賞吳天賞引用關係
指導教授(外文):Tain-Shung Wu
學位類別:博士
校院名稱:國立成功大學
系所名稱:化學系碩博士班
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2003
畢業學年度:91
語文別:中文
論文頁數:221
中文關鍵詞:小紅參大理茜草大葉樹蘭降真香
外文關鍵詞:Rubia yunnanensisRubia ustulataAglaia elliptifoliaAcronychia pedunculata
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小紅參 (Rubia yunnanensis Diels)為茜草科 (Rubiaceae)茜草屬 (Rubia)植物。由其根部共分離45個化合物,經光譜方法、葡萄糖酵素水解以及與文獻比對光譜資料後確認37個化合物之結構,其中11個為首次分離得到的新化合物分別為 rubiayannone-A、rubinaphthins-A~D、2-carbomethoxyanthraquinone、rubiarbonone-D~F與rubiarboside-F~G;2-carbomethoxyanthraquinone為首次由植物中分離得到,而baicalin 與2-hydroxymethylanthraquinone為首次由茜草屬植物分離得到。另外,經由氨基酸分析儀分析,得知含有28種氨基酸。
大理茜草 (Rubia ustulata Diels)亦為茜草科 (Rubiaceae)茜草屬 (Rubia)植物。由其根部共分離得到50個化合物,經光譜方法以及與文獻比對光譜資料後確認26個化合物之結構,其中2個為首次分離得到的新化合物分別為rubiayannone-A與rubilatin-A。另外,經由氨基酸分析儀分析,得知含有37種氨基酸。
大葉樹蘭 (Aglaia elliptifolia)為楝科 (Meliaceae)樹蘭屬 (Aglaia)植物。由其莖皮共分離得到14個化合物,經光譜方法、化學反應以及與文獻比對光譜資料後確認5個化合物之結構,其中aglafolin為新化合物。
降真香 (Acronychia pedunculata)為芸香科 (Rutaceae)降真香屬 (Acronychia)植物。由其根皮共分離得到7個化合物,經光譜方法以及與文獻比對光譜資料後確認6個化合物之結構,其中acronyculatin-B為新化合物。
經藥理測試後發現從大葉樹蘭所分離到的aglafolin在濃度100 μg/ml下對由arachidonic acid (AA) 100 μM 和platelat-activating factor (PAF) 2 ng/ml所引起的血小板凝集具有完全抑制的功效;由小紅參所分離到的1,3-dihydroxyanthraquinone、1,3,6-trihydroxy-2-methylanthraquinone和rubiarbonone-B在濃度150 μM對由AA和collagen所引起的血小板凝集具有抑制效果;而 rubiarbonone-A和rubiarbonol-A在濃度150 μM對由AA、collagen、PAF和thrombin (Thr)所引起的血小板凝集具有促進凝集的效果。此外,從大葉樹蘭所分離到的aglafolin和rocaglamide均對鼻咽癌細胞(KB)、人類肺癌細胞 (A-459)、人類大腸癌細胞 (HCT-8)、老鼠淋巴癌細胞 (P-388)、人類黑色素瘤細胞 (RPMI-7951)、人類腦癌細胞 (TE-671)具有非常強的細胞毒活性。
由本研究結果發現由小紅參與大理茜草所分得之蒽醌 (anthraquinone)類化合物其羥基取代位置大都是屬於A和D類型取代;同時也發現較多種類的arbonane類型triterpenoid類化合物,而此類型化合物一般在植物成分中較少見,這些發現對於植物的化學分類具很重要的意義。
Eleven new compounds together with twenty-six known compounds were isolated and characterized from the root of Rubia yunnanensis Diels. Their structures were elucidated by spectral analysis and glucosidase hydrolysis, and by comparison of their physical and spectral data with the literature values. The new compounds included rubia- yannone-A, rubinaphthins-A~D, 2-carbomethoxyanthraquinone, rubiarbonone-D~F and rubiarboside-F~G. 2-Carbomethoxyanthraquinone was the first report from plant source. Baicalin and 2-hydroxymethylanthraquinone were isolated for the first time from the genus Rubia. Besides, twenty-eight amino acids were also detected by the amino acid analyzer.
Two new and twenty-four known compounds were separated and characterized from the root of Rubia ustulata Diels. Their structures were elucidated by spectral analysis and comparison of their physical and spectral data with the literature values. The new compounds included rubiayannone-A and rubilatin-A. In addition, thirty-seven amino acids were characterized by the amino acid analyzer.
One new compound aglafolin together with four known compounds were obtained and characterized from the stem barks of Aglaia elliptifolia. Their structures were elucidated by means of spectral analysis and chemical conversion, and comparison of their physical and spectral data with the literature values.
One new compound acronyculatin-B together with five known compounds were isolated and characterized from the root barks of Acronychia pedunculata. Their structures were elucidated by spectral analysis and comparison of their physical and spectral data with the literature values.
Some of the isolated compounds were subjected to evaluate their pharmacological activities. Aglafolin showed the completely platelet aggregation at concentration 100 μg/ml caused by arachidonic acid (AA) 100 μM and platelet-activating factor (PAF) 2 ng/ml. 1,3-Dihydroxyanthraquinone, 1,3,6-trihydroxy-2-methylanthraquinone and rubiarbonone-B isolated from the root of R. yunnanensis Diels showed slight inhibition of platelet aggregation caused by AA and collagen at 150 μM, whereas rubiarbonone-A and rubiarbonol-A isolated from the same plant showed the promotion of platelet aggregation caused by AA, collagen, PAF and thrombin (Thr) at 150 μM. Aglafolin and rocaglamide isolated from Aglaia elliptifolia showed significant cytotoxicity in KB (nasal pharyngeal carcinoma), A-549 (human lung carcinoma), P-388 (murine leukemia), TE-671 (human medulloblastoma), RPMI-7951 (human melanoma) and HCT-8 (human colon carcinoma) cancer cell lines.
In our study, the substitution pattern of hydroxyl group on the most of anthra- quinones isolated from R. yunnanensis and R. ustulata belong to A and D substituted types. We also found the rich arbornane triterpenoids in R. yunnanensis Diels and Rubia ustulata Diels. This is a very important chemotaxonomic mark of plants.
目 錄 …………………………………………………………I
中文摘要 …………………………………………………………III
英文摘要 …………………………………………………………IV
第一章 緒論……………………………………………………1
第一節 研究動機………………………………………………1
第二節植物形態………………………………………………2
第二章植物之研究概況………………………………………7
第一節植物之成分研究回顧…………………………………7
第二節茜草屬植物之生物活性研究概況……………………75
第三節樹蘭屬植物之生物活性研究概況……………………76
第四節降真香屬植物之生物活性研究概況…………………78
第三章抽取與分離……………………………………………79
第一節小紅參根部之抽取與分離……………………………79
第二節大理茜草根部之抽取與分離…………………………85
第三節大葉樹蘭莖皮之抽取與分離…………………………92
第四節降真香根皮之抽取與分離……………………………94
第四章化合物之構造研究……………………………………96
第一節光譜特徵………………………………………………96
第二節2-Carbomethoxyanthraquinone (599)之構造研究…98
第三節Rubiayannone-A (602)之構造研究…………………102
第四節Rubinaphthin-A (603)之構造研究…………………107
第五節Rubinaphthin-B (604)之構造研究…………………112
第六節Rubinaphthin-C (605)之構造研究…………………117
第七節Rubinaphthin-D (606)之構造研究…………………122
第八節Rubiarbonone-D (607)之構造研究…………………127
第九節Rubiarbonone-E (608)之構造研究…………………132
第十節Rubiarbonone-F (609)之構造研究…………………137
第十一節 Rubiarboside-F (610)之構造研究…………………142
第十二節 Rubiarboside-G (611)之構造研究…………………147
第十三節 Rubilatin-A (643)之構造研究………………………152
第十四節 Aglafolin (242)之構造研究…………………………157
第十五節 Acronyculatin-B (657)之構造研究…………………161
第十六節 其它化合物的構造研究.………………………………167
第五章藥理活性研究……………………………………………168
第一節抗血小板凝集活性試驗…………………………………168
第二節細胞毒活性試驗…………………………………………168
第六章茜草屬植物成分比較……………………………………171
第七章結論………………………………………………………173
第八章實驗部分……………………………………………………175
第一節本實驗所使用之儀器與藥品……………………………175
第二節小紅參根部之抽取與分離………………………………176
第三節大理茜草根部之抽取與分離……………………………178
第四節大葉樹蘭莖皮之抽取與分離……………………………180
第五節降真香根皮之抽取與分離………………………………180
第六節抗血小板凝集活性試驗…………………………………181
第七節細胞毒活性試驗…………………………………………182
第八節化合物光譜數據整理……………………………………184
參考文獻…………………………………………………………203
本研究相關已發表之論文………………………………………………………221
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