海洋生態系的多樣性造就了海洋的二次代謝物在結構上及生物活性方面的豐富度，為了尋找新奇且具有生物活性的二次代謝物，本篇論文主要是針對綠島海域採集之異傘軟珊瑚Heteroxenia mindorensis進行二次代謝物之分析研究，從軟珊瑚H. mindorensis 的丙酮萃取物中共純化得到八個新的繆肉烷類化合物1–8、一個新的germacrane類化合物10、一個新的oplopane類化合物11及一個已知的化合物γ-muurolene (9)。本研究分離之二次代謝物結構鑑定，主要是利用有機光譜的分析，有紅外線光譜、紫外線光譜、高低解析質譜、一維及二維NMR，以及與已知化合物之文獻比對其光譜資料來確定，而化合物1之絕對立體位向的決定是運用Mosher的方法加以證明。此外並針對化合物1–11進行人類肺癌細胞(A-549)、人類直腸癌細胞(HT-29)毒殺活性測試，化合物1、8對A-549癌細胞有顯著的毒殺活性，而化合物2、9對HT-29癌細胞有顯著的毒殺活性。

The distinct biodiversity of marine habitats is reflected by the structural and bioactivity diversity of secondary metabolites found in marine organisms. In order to search for novel and bioactive secondary metabolites, chromatographic separation on the acetone extract of the soft coral Heteroxenia mindorensis, collected at the Green Island resulted in the isolation of eight new muurolane sesquiterpenoids 1–8, one new germacrane sesquiterpenoid 10, one new oplopane sesquiterpenoid 11 and one known analogue γ-muurolene (9). The structures of these sesquiterpenoids were elucidated on the basis of their spectroscopic analyses comprising IR, UV, LRESIMS, HRESIMS, LREIMS, 1D NMR, 2D NMR, and by comparison with reported data in literatures. The absolute stereochemistry of 1 was further determined by application of the Mosher’s method. The cytotoxicity of metabolites 1–11 against HT-29 (human colon adenocarcinoma) and A-549 (human lung epithelial carcinoma) cells were evaluated in vitro. Metabolites 1 and 8 exhibited significant cytotoxic activity against A-549. Metabolites 2 and 9 exhibited significant cytotoxic activity against HT-29.

論文審定書 i
謝辭 ii
中文摘要 iii
英文摘要 iv
化合物1–11之化學結構 v
目錄 vi
表次 ix
圖次 x
縮寫對照表 xvii

壹、緒論 1
一、前言及研究動機與目的 1
二、 軟珊瑚Heteroxenia mindorensis二次代謝物化學研究回顧 2
1、 Cadalane二次代謝物 2
2、 Sterol二次代謝物 5
3、 Ceramide二次代謝物 6
4、 Muurolane類二次代謝物 8
5、 Oplopane二次代謝物 18
6、 Germacrane二次代謝物 21
貳、材料與研究方法 24
Heteroxenia mindorensis樣品採集、分類地位及分離流程 24
1、 樣品採集時間、地點與鑑定 24
2、 軟珊瑚Heteroxenia mindorensis之分類地位 24
3、 軟珊瑚Heteroxenia mindorensis之萃取與分離流程 24
4、 軟珊瑚Heteroxenia mindorensis二次代謝物之純化分離 27
(1) 化合物9之純化分離 27
(2) 化合物10、4、5、6和3之純化分離
(3) 化合物2、11和1之純化分離
(4) 化合物7和8之純化分離 27
31
33
參、異傘軟珊瑚Heteroxenia mindorensis之化合物結構鑑定 35
一、化合物1之結構解析 35
二、化合物2之結構解析 55
三、化合物3之結構解析 70
四、化合物4之結構解析 84
五、化合物5之結構解析 99
六、化合物6之結構解析 114
七、化合物7之結構解析 129
八、化合物8之結構解析 143
九、化合物9之結構判定 157
十、化合物10之結構解析 167
十一、化合物11之結構解析 181
肆、生物活性之測試 195
一、細胞毒殺活性測試方法 195
二、MTT分析原理 195
三、活性測試結果 196
伍、結論 197
陸、參考文獻 199
柒、附錄 204
一、實驗設備儀器及材料 204
1、實驗設備儀器 204
2、實驗材料 205
二、Mosher醯化反應的原理與製備 206

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