臺灣博碩士論文加值系統

中文摘要
在台灣紅豆杉的抗腫瘤成份研究中，為了尋求臨床有效之烷類紫杉醇衍生物並對其相關化合物進行結構與活性的分析，本實驗以在台中縣及南投縣所採集之紅豆杉枝葉為材料，分別經以細胞毒殺活性為指標的篩選，對其紫杉烷類天然物進行研究，初步得到8個紫杉烷類化合物，經IR、UV光譜、一維及二維核磁共振圖譜 (DEPT、COSY、HMBC等) 分析確認為：2-deacetoxy taxinine J （77）、1β-hydroxy-5α-deacetylbaccatin I （78）、taxumairol Z（79）、taxayuntin G（80）、taxuspine F （81）、 wallifoliol（82）、taxumairol Q（83）10-deacetylbaccatin III（84）。
此外，針對含compound 82之fraction進行乙醯化反應及苯醯化反應得到一系列的化合物85∼89經由核磁共振、質譜及各種光譜證實為：7, 13-diacetylwallifoliol （85）、9, 13 - diacetyl taxumairol W （86）、7, 13-dibenzoylwallifoliol （87）、10, 13 - O- dibenzoyltaxacustin（88）、7, 9-dibenzoyltaxumairol P（89），而化合物79 、83為首度自天然界分離之新化合物，化合物78 、80-82為第一次在台灣紅豆杉被發現，化合物85-89為新的衍生物，將這一系列的化合物送往中國醫藥研究所進行細胞毒殺活性實驗，並探討化合物結構與生物活性間的關係。

ABSTRACT
To search for practical sources of potential useful taxoids and study the structure and activity relationship of taxoids, the leaves of Formosan Taxus mairei was extracted with n-hexane, ethanol, acetone and methanol, respectively. Extensive column and preparative thin layer chromatography by bioassay-directed screening resulted in the isolation of 8 taxoids. Their structures were identified as 2-deacetoxy taxinine J （77） 、1β-hydroxy-5α-deacetyl baccatin I（78）、taxumairol Z（79）、taxayuntin G（80）、taxuspine F（81）、 wallifoliol（82）、taxumairol Q （83）、1-deacetyl baccatin III（84）. The compound 82-containg fraction from another batch of material was acylated to yield a series of derivatives and their structures were identified as 7, 13-diacetylwallifoliol（85）、9, 13 - diacetyltaxumairol W（86）、7, 13-dibenzoylwallifoliol（87）、10, 13 - dibenzoyltaxacustin（88）、7, 9-dibenzoyl taxumairol P（89） primarily on the basis of 1- and 2-D NMR techniques including DEPT, COSY and HMBC experiments as well as chemical correlation with know compounds. Among them, compound 79 、83 was first isolated in nature, compounds 78 and 80-82 were first isolated from T. mairei and compounds 85-89 were new derivatives. All of these compounds were sent to National Research Institute of Chinese Medicine for antitumor test in vitro. The investigation of their structure and activity relationship is now in progress.

目 錄
一、緒論 頁次
（一）前言…………………………………………………..1
（二）紅豆杉簡介…………………………………………..3
（三）紅豆杉Taxoids天然物最近之研究…………………5
（四）台灣紅豆杉根部相關之成份介紹………………….18
（五）台灣紅豆杉種子相關之成份介紹………………….21
（六）台灣紅豆杉樹皮相關之成份介紹………………….25
（七）台灣紅豆杉枝葉相關之成份介紹………………….28
（八）研究目的…………………………………………….31
二、材料與方法
（一）材料………………………………………………….32
（二）分離方法之簡述…………………………………….32
三、結果與討論
（一）成份Tax-a（77）之結構鑑定……………………...39
（二）成份Tax-b（78）之結構鑑定……………………...42
（三）成份Tax-c（79）之結構鑑定……………………...45
（四）成份Tax-d（80）之結構鑑定……………………...49
（五）成份Tax-e（81）之結構鑑定……………………..52
（六）成份Tax-f（82）之結構鑑定……………………..55
（七）成份Tax-g（83）之結構鑑定…………………….58
（八）成份Tax-h（84）之結構鑑定…………………….61
（九）討論………………………………………………...64
四、衍生物的製備
（一）化合物85之結構鑑定…………………………….71
（二）化合物86之結構鑑定…………………………….73
（三）化合物87之結構鑑定…………………………….76
（四）化合物88之結構鑑定…………………………….78
（五）化合物89之結構鑑定…………………………….81
五、實驗部份
（一）儀器與材…………………………………………..85
（二）成份之分離方法…………………………………..86
（三）化合物77之分離純化……………………………88
（四）化合物78之分離純化……………………………89
（五）化合物79之分離純化……………………………90
（六）化合物80之分離純化……………………………91
（七）化合物81之分離純化…………………………...92
（八）化合物82之分離純化…………………………...93
（九）化合物83之分離純化…………………………...94
（十）化合物84之分離純化…………………………...95
（十一）化合物85之分離純化…………………………96
（十二）化合物86之分離純化…………………………97
（十三）化合物87之分離純化…………………………98
（十四）化合物88之分離純化…………………………99
（十五）化合物89之分離純化………………………..100

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