海洋無脊椎動物至今已被發現不少具有生物活性的二次代謝產物，在過去研究中，發現Sinularia、Lobophytum和Clavularia屬之軟珊瑚具有許多不同骨架的二次代謝物，有許多化合物都具有特殊的生物活性，本論文主要針對東沙環礁海域指形軟珊瑚(Sinularia leptoclados)、三仙台海域之葉形軟珊瑚(Lobophytum crassum)和綠島之踺形羽軟珊瑚(Clavularia viridis)的二次代謝物進行分析研究。從軟珊瑚S. leptoclados進行天然物萃取，經過各種層析技術之純化，分離出1個已知diterpenoid化合物1及1個新guaiane類化合物2；在軟珊瑚L. crassum之有機萃取中分離得到一個已知化合物3及三個新的cembranoids類化合物4–6。另外，從軟珊瑚C. viridis的EtOAc萃取物中純化出兩個新的fatty acid類化合物7和8與已知化合物9–15。這些二次代謝物的結構鑑定，主要是透過其有機光譜的分析(包含紅外線光譜、紫外線光譜、質譜、比旋光、一維及二維NMR)以及與已知化合物之文獻比對光譜資料而確定結構。此外並針對化合物2和4–9進行人類肺癌細胞(A-549)、人類直腸癌細胞(HT-29)及老鼠血癌細胞(P-388)毒殺活性測試，以及進行抗人類巨細胞病毒(HCMV)測試，發現化合物4、7和9對A-549、HT-29和P-388皆有毒殺活性。

Marine invertebrates have been found to be a rich source of bioactive secondary metabolites. Soft corals of the genus Sinularia, Lobophtum, and Clavularia were found to possess different skeletons secondary metabolites. Therefore we have investigated the secondary metabolites of the soft corals Sinularia leptoclados, Lobophtum crassum, and Clavularia viridis. Investigations on the chemical constituents of S. leptoclados collected at Dongsha Atoll of the South China Sea have led to the isolation of one known diterpenoid 1 and one new guaiane-type compound 2. Chromatographic separation of the organic extracts of the Formosan soft coral L. crassum, collected at San-Shen-Tai, led to the isolation of one known diterpenoid 3, together with three new cembranoids 4–6. In addition, the EtOAc extract of C. viridis, collected at the Green Island, yielded two new fatty acids 7 and 8, along with three known compounds 9–15.The structured elucidations of these compounds were determined on the basis of their spectroscopic analysis (IR, ESIMS, specific optical rotations, 1D NMR and 2D NMR) and by comparison of the physical and spectral data with those of the related known compounds.The cytotoxicity against of P-388 (murine lymphocytic leukemia), HT-29 (human colon adenocarcinoma), and A-549 (human lung epithelial carcinoma) cells as well as the anti-HCMV (human cytomegalovirus) activities of metabolites 2 and 4–9 were evaluated in vitro. Metabolites 4, 7 and 9 exhibited significant cytotoxic activity against A-549, HT-29 and P-388.

目 錄
論文審定書 i
謝辭 ii
中文摘要 iii
英文摘要 iv
化合物1–15之化學結構 v
目錄 vi
表次 ix
圖次 xi
縮寫對照表 xvi

壹、緒論 1
一、前言及研究動機與目的 1
二、指形軟珊瑚 Sinularia leptoclados 二次代謝物研究回顧 3
1. Cembrane類 3
2. Steroid類 7
3. Lipid和guaiane類 10
4. Spatane類 13
三、葉形軟珊瑚Lobophytum crassum二次代謝物研究回顧 14
1. Cembrane類 14
2. Steroid類 22
3. Glycolipid類 24
4. Terpenoid類 25
四、踺形羽軟珊瑚Clavularia viridis二次代謝物研究回顧 26
1. Prostanoid類 26
2. Steroid類 36
貳、材料與研究方法 40
一、Sinularia leptoclados 樣品採集、分類地位及分離流程 40 vii
1.樣品採集時間、地點與鑑定 40
2.樣品之分類地位 40
3.萃取與分離流程 41
4.指形軟珊瑚 S. leptoclados 之分離純化 43
(1) 化合物 1 和 2 之純化分離 43
二、Lobophytum crassum 樣品採集、分類地位及分離流程 44
1.樣品採集時間、地點與鑑定 44
2.樣品之分類地位 44
3.萃取與分離流程 45
4.葉形軟珊瑚 L. crassum 之分離純化 47
(1) 化合物 3–5 之純化分離 47
(2) 化合物 6 之純化分離 48
三、Clavularia viridis 樣品採集、分類地位及分離流程 49
1.樣品採集時間、地點與鑑定 49
2.樣品之分類地位 49
3.萃取與分離流程 50
4.踺形羽軟珊瑚 C. viridis 之分離純化 52
(1) 化合物 7、8 和 15 之純化分離 52
(2) 化合物 9、10 和 14 之純化分離 54
(3) 化合物 11–13 之純化分離 55
参、化合物之結構解析 57
一、指形軟珊瑚 Sinularia leptoclados 之化學成分 57
1.化合物 1 之結構判定 57
2.化合物 2 之結構解析 64
二、葉形軟珊瑚 Lobophytum crassum 之化學成分 81
1.化合物 3 之結構判定 81
2.化合物 4 之結構解析 87
3.化合物 5 之結構解析 106
4.化合物 6 之結構解析 125
三、踺形羽軟珊瑚 Clavularia viridis 之化學成分 144
1.化合物 7 之結構解析 144
2.化合物 8 之結構解析 156
3.化合物 9 之結構判定 180
4.化合物 10 之結構判定 186
5.化合物 11 之結構判定 191
6.化合物 12 之結構判定 198
7.化合物 13 之結構判定 204
8.化合物 14 之結構判定 211
9.化合物 15 之結構判定 216
肆、生物活性之測試 221
一、細胞毒殺活性測試方法 221
二、MTT 分析原理 221
三、抗 HCMV 病毒的測試方法 222
四、活性測試結果 222
伍、結論 224
陸、參考文獻 225
柒、附錄 239
一、實驗設備儀器及材料 239
1.實驗設備儀器 239
2.實驗材料 240
二、碩士論文公開授權書 241

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