本次研究從台灣海域所採集的白錦花軟珊瑚Litophyton chabrolii有機萃取層中分離出11個prenylbicyclogermacrane的化合物，其中有7個化合物(1、5與7–11)為新發現的化合物，剩餘4個為已知的化合物，包含pacificin A (2)、pacificin O (3)、palmatol (4)與化合物6，本文中有推論化合物1–11可能的生合成路經。為了解釋prenylbicyclogermacrane骨架化合物的化學位移等訊息，藉由收集此類骨架的化合物資訊進行分析，進而說明18號與20號甲基受到環丙烷的遮蔽效應產生的影響，或是藉由耦合常數來解釋prenylbicyclogermacrane中1,2-雙取代的環丙烷構形。
文獻上記載肉質軟珊瑚屬Sarcophyton中具有非常豐富的活性二次代謝物，從養殖型花環肉質軟珊瑚Sarcophyton trocheliphorum的有機萃取層中分離出兩個已知的cembrene-type化合物(12與13)，當化合物13在以CDCl3為溶劑時非常不穩定且會在數分鐘內降解，故將兩個cembrene-type的化合物使用C6D6¬作為溶劑來取得NMR光譜資料。這些化合物的結構與相對立體構型皆是使用光譜資訊(NMR、IR、UV與旋光)配合質譜(MS)所建立，藉由比對文獻中相似的已知化合物結構資訊，來確定化合物結構是否正確。

Eleven prenylbicyclogermacrane-type diterpenes (1–11) were isolated from the organic extract of the Formosan soft coral Litophyton chabrolii, including seven new compounds (1, 5 and 7–11) and four known compounds, pacificin A (2)、pacificin O (3)、palmatol (4) and compound 6. Possible biosynthesis pathways of the compounds 1–11 were proposed. To explain the chemical shift of prenylbicyclogermacrane skeleton compounds, the skeleton data were collected and analyzed. It shows the shielding effect for 18-methyl group and 20-methyl group and coupling constant for 1,2-trans three member ring structure from prenylbicyclogermacrane skeleton in
literatures.
Soft corals of the genus Sarcophyton havd been reported to be a rich source of secondary metabolited compounds with biological activities. Two known cembrene-type compounds (12 and 13) were isolation from the organic extract of the cultured soft coral Sarcophyton trocheliphorum. When compound 13 disolved in CDCl3 solvent, it is very unstable and easy decomposed in few minutes. Both of two cembrene-type compounds were using C6D6 as solvent system to gain NMR spectra.The structures and the relative configurations of the compounds were determined by spectral data (NMR, IR, UV, optical rotation) and MS data. All of compounds were confirmed by the literatures with those of the related known
compounds.

論文審定書………………………………………………………………………….…i
謝辭……………………………………..…………………………………………….ii
摘要……………………………………..…………………………………………….iii
Abstract……………………………….….……………………..…….………………iv
化合物1–13之化學結構…………….….……………………………………………v
圖次……………………………………….…………………………………………viii
表次…………………………………………………………………………..…….xiv
縮寫對照表……………………………………………………………………....…xxii

壹、緒論 1
一、研究背景與目的 1
二、白錦花軟珊瑚Litophyton chabrolii屬名變更 3
三、錦花軟珊瑚屬 Litophyton sp.之二次代謝物文獻回顧 4
1.倍半萜類 Sesquiteroenes 4
2.雙萜類 Diterpenes 8
3.固醇類 Steroids 15
四、花環肉質軟珊瑚Sarcophyton trocheliophorum之文獻回顧 20
五、Prenylbicyclogermacrane骨架之生合成與特徵訊號分析 31
貳、生物材料與研究方法 41
一、生物材料前處理 41
二、Litophyton chabrolii採集與分類 42
三、Litophyton chabrolii的分離流程 43
四、Sarcophyton trocheliophorum採集與分類 49
五、Sarcophyton trocheliophorum的分離流程 50
六、實驗器材與溶劑 53
參、實驗結果與化合物結構解析 55
一、白錦花軟珊瑚 Litophyton chabrolii分離之化合物 55
1、化合物1之結構解析 55
2、化合物2之結構解析 73
3、化合物3之結構解析 83
4、化合物4之結構解析 91
5、化合物5之結構解析 101
6、化合物6之結構解析 113
7、化合物7之結構解析 123
8、化合物8之結構解析 134
9、化合物9之結構解析 147
10、化合物10之結構解析 158
11、化合物11之結構解析 170
二、養殖型肉質軟珊瑚Sarcophyton trocheliophorum分離之化合物 183
1、化合物12之結構解析 183
2、化合物13之結構解析 193
肆、結論 205
伍、參考文獻 207

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