本研究主要由台灣海域所採集的兩種軟珊瑚仿穗軟珊瑚Paralemnalia digitiformis和白穗軟珊瑚Nephthea chabroli及台灣多扇藻Homoeostrichus formosana的有機萃取物中找尋具有生物活性的化學成分。從軟珊瑚Paralemnalia digitiformis有機萃取物進行色譜分離得到2個化合物，包括一個新neolemnane type化合物(1)以及1個已知化合物nardosinane-type sesquiterpenoid (2)；從台灣多扇藻Homoeostrichus formosana有機萃取物進行色譜分離得到6個化合物，包含兩個新chroma(e)ne derivative化合物 (3、4)以及4個已知化合物fucosterol (5)、cholest-5-en-3β-ol (6)、phytol (7)及γ-tocophernol (8); 從軟珊瑚Nephthea chabroli有機萃取物進行色譜分離得到兩個新dollabellane type化合物 (9、10)， prenylbicyclogermacrane type化合物 (11)及新骨架化合物(12)和2個已知化合物pacificin A (13)、7β-acetoxy-24-methylcholesta-5-24(28)-diene-3,19-diol (14)。這些化合物的化學結構均由詳細的光譜資料所分析 (IR, MS, 1D、2D NMR)和比對文獻上的已知化合物相關的物理性質及光譜資料而建立。化合物1−14對於A-549 (人類肺癌細胞)、HT-29 (人類直腸癌細胞)進行毒殺活性測試，其中化合物14對HT-29有顯著的抑制活性。

In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of Formosan soft corals Paralemnalia digitiformis and Nephthea chabroli as well as Formosan brown alga Homoeostrichus formosana. Chromatographic frctionation of the organic solubles of Paralemnalia digitiformis has led to isolation of a new neolemnane type sesquiterpene (1) and a known compound, nardosinane type-sesquiterpenoid (2). Chromatographic purification of the organic solubles of Homoeostrichus formosana has led to the isolation of six compounds, including two new chroma(e)ne deriactives (3 and 4) along with four known compounds, fucosterol (5), cholest-5-en-3β-ol (6), phytol (7), and γ-tocophernol (8). Chromatographic separation of the organic solubles of Nephthea chabroli has led to isolation of two new dollabellane type diterpenoids (9 and 10), new prenylbicyclogermacrane diterpenoid 11 and diterpene 12 having a new skelton as well as two known compounds, pacificin A (13) and 7β-acetoxy-24-methylcholesta-5-24(28)-diene-3,19-diol (14). The structures of these compounds were established by the detailed spectroscopic analysis (IR, MS, 1D/2D NMR) and by comparison with physical and spectral data with those of literatures. The cytotoxicity of metabolites 1−14 against A-549 (human lung epithelial carcinoma) cell and HT-29 (human colon adenocarcinoma) were evaluated. Metabolite 14 exhibited significant cytotoxicity against HT-29 in vitro.

論文審定書 i
論文公開授權書 ii
謝辭 iii
中文摘要 iv
Abstract v
化合物1−14之化學結構 vi
表次 ix
圖次 x
縮寫對照表 xiv

壹、 緒論 1
一、 研究背景及目的 1
二、 仿穗軟珊瑚Paralemnalia digitiformis所含二次代謝物之文獻回顧 2
1. Neolemnane類二次代謝物研究回顧 2
三、 褐藻Homoeostrichus formosana所含二次代謝物文獻回顧 4
1. Chroma(e)ne derivactive二次代謝物研究回顧 4
四、 白穗軟珊瑚Nephthea chabroli所含二次代謝物之文獻回顧 7
1. Dollabellane類二次代謝物研究回顧 7
2. Prenylbicyclogermacrane類二次代謝物研究回顧 12
3. Nephthea chabroli二次代謝物研究回顧 14
貳、 生物材料與研究方法 20
一、 研究流程 20
二、 Paralemnalia digitiformis物種的採集及分類地位 21
三、 Paralemnalia digitiformis的分離流程 22
四、 Homoeostrichus formosana物種的採集及分類地位 24
五、 Homoeostrichus formosana的分離流程 25
六、 Nephthea chabroli物種的採集及分類地位 28
七、 Nephthea chabroli的分離流程 29
八、 實驗器材與溶劑 33
參、 實驗結果與化合物構造解析 35
一、 仿穗軟珊瑚Paralemnalia digitiformis分離之化合物 35
1. 化合物1結構解析 35
2. 化合物2結構判定 48
二、 褐藻Homoeostrichus formosana分離之化合物 52
1. 化合物3結構解析 52
2. 化合物4結構解析 67
3. 化合物5結構判定 79
4. 化合物6結構判定 89
5. 化合物7結構判定 99
6. 化合物8結構判定 109
三、 白穗軟珊瑚Nephthea chabroli分離之化合物 119
1. 化合物9結構解析 119
2. 化合物10結構解析 133
3. 化合物11結構解析 145
4. 化合物12結構解析 158
1. 化合物13結構判定 171
2. 化合物14結構判定 175
肆、 生物活性測試 185
一、 細胞毒殺試驗 185
1. 細胞毒殺試驗方法 185
2. MTT分析原理 185
二、 生物活性試驗結果 187
1. 細胞毒殺試驗結果 187
伍、 結論 188
陸、 參考文獻 190

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