Sinularia sp.之軟珊瑚具有許多不同骨架的二次代謝物，且具有特殊的生物活性，本研究針對綠島海域指型軟珊瑚Sinularia mollis進行天然物研究，經過各種層析技術之純化，分離出七個新化合物，其中化合物1及 2為新骨架化合物(2-methyl-6-oxo-2-hepten-4-olide及3-methyl-6-oxo-2-hepten-4-olide)、化合物3－5為三個新的steroids類化合物、化合物7為新的11,12-secocembrane-type diterpenoid 化合物、化合物9為新的cembrane-type diterpenoid 化合物及七個已知化合物(3S,23R, 24S)-ergost-5-ene-3β,23α-25-triol (6)、11,12-secoflexibillin (8)、querciformilin C (10)、11-epi-sinulariolide acetate (11)、14-deoxycrassin (12)、sinulariolone (13) 與flexibilisquinone (14)。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、圓二色光譜、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決定。此外，並針對化合物1－9和14進行老鼠血癌細胞(P-388)、人類肺癌細胞(A549) 及人類直腸癌細胞(HT-29)之毒殺活性測試，以及進行抗人類巨細胞病毒(HCMV)測試，化合物 3和6對老鼠血癌細胞(P-388)有顯著的活性(ED50= 2.5和2.3 μg/mL)。

The soft coral Sinularia sp. was found to be a rich source of biological and special secondary metabolites. Continuing investigation on the chemical constituents of Sinularia sp. has led to the isolation of seven new compounds, including two new compounds of novel skeletons, 2-methyl-6-oxo-2-hepten-4-olide (1) and 3-methyl-6- oxo-2-hepten-4-olide (2), three new steroids (3－5), a new 11,12-secocembrane-type diterpenoid (7) and a new cembrane-type diterpenoid (9), along with seven known compounds, (3S,23R, 24S)-ergost-5-ene-3β,23α-25-triol (6), 11,12-secoflexibillin (8), querciformilinC (10), 11-epi-sinulariolideacetate (11), 14-deoxycrassin (12), singulariolone (13) and flexibilisquinone (14)。
The structures of these compounds were determined on the basis of their spectroscopic analysis (1H, 13C NMR, 1H–1H COSY, HSQC, HMBC, IR, UV, CD and HRESIMS), the cytotoxicity of P-388 (murine lymphocytic leukemia), HT-29 (human colon adenocarcinoma), and A549 (human lung epithelial carcinoma) cells as well as the anti-HCMV (human cytomegalovirus) activities of metabolites 1－9, 14 were evaluated. Metabolites 3 and 6 exhibited significant activity against P-388 cell in vitro (ED50= 2.5和2.3 μg/mL).

論文審定書 i
謝詞 ii
中文摘要 iii
英文摘要 iv
新化合物1－5, 7, 9結構與已知化合物6, 8, 10－14 v
目錄 vi
表次 ix
圖次 xi
縮寫對照表 xvii

壹、緒論 1
一、前言及研究動機與目的 1
二、指型軟珊瑚 Sinularia mollis 二次代謝物研究回顧 3
1、Cembrane類二次代謝物研究回顧 3
2、Steroid類二次代謝物研究回顧 17
貳、Sinularia mollis樣品採集及分離流程 24
一、指型軟珊瑚Sinularia mollis樣品採集時間、地點與鑑定 24
二、指型軟珊瑚Sinularia mollis之分類地位 25
三、指型軟珊瑚Sinularia mollis之萃取與分離流程 26
四、指型軟珊瑚Sinularia mollis之分離純化 27
1、 GN89-9-1-1 (1)與GN89-9-1-12 (9)之純化分離 27
2、 GN89-11-2-1 (5)之純化分離 28
3、 GN89-12-41 (3)、GN89-12-82(4)、GN89-12-73 (6)
與 GN89-12-24 (7)之純化分離 28
4. GN89-13-101-1 (8)、GN89-13-23 (10)、GN89-13-24 (11)、
GN89-13-20 (12)與GN89-13-26 (14)之純化分離 30
5. GN89-17-1-5 (2)與 GN89-17-3-11 (13)之純化分離 32
参、化合物之結構解析 33
一、指型軟珊瑚Sinularia mollis之化學成分的結構證明 33
1、GN89-9-1-1 (1)之結構解析 33
2、GN89-17-1-5 (2)之結構解析 44
3、GN89-12-41 (3)之結構解析 55
4、GN89-12-82 (4)之結構解析 74
5、GN89-13-20 (5)之結構解析 93
6、GN89-12-72 (6)之結構判定 113
7、GN89-13-101-1 (7)之結構解析 119
8、GN89-12-24 (8)之結構判定 137
9、GN89-9-1-12 (9)之結構解析 145
10、GN89-13-23 (10)之結構判定 163
11、GN89-13-24 (11)之結構判定 169
12、GN89-13-20 (12)之結構判定 175
13、GN89-17-3-11 (13)之結構判定 181
14、GN89-13-26 (14)之結構判定 187
肆、生物活性之測試 193
一、細胞毒殺活性測試方法 193
二、MTT分析原理 193
三、抗HCMV病毒的測試方法 194
四、活性測試結果 195
伍、結論 196
陸、參考文獻 198
柒、附錄 203
1、實驗設備儀器 203
2、實驗材料 204

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