臺灣綠島產軟珊瑚Cespitularia sp.的萃取物，以矽膠管柱層析，
葡聚醣凝膠(Sephadex LH-20)，及正、逆相高壓液相層析儀進行分離純化，得到五個新的化合物G8-7-7-A (1)、G8-9-15-30-A (2)、G8-10-B(3)、G8-7-6-A (4)、G8-7-5-A (5)。這五個化合物(1-5)皆是具有C-16,C-17, C-19 三支甲基的雙萜類化合物，以及C-4, C-18 環外雙鍵。化合物1 和2 是norditerpene 骨架，具雙圓環。G8-7-7-A (1)是由6, 13 圓環組成，C-7, C-8 間有環內雙鍵，C-6 醇基取代，C-10, C-11間以lactone 環連結，且C-12 有酮基取代。G8-9-15-30-A (2)之基本構形與G8-7-7-A (1)相似，但環內雙鍵位移為C-8, C-9 間，lactone 環轉為C-10, C-12 之間連結，且C-11 變為酮基，故其為6, 14 圓環組成。
化合物3-5 為diterpene 之verticillane 骨架，具三圓環，為5,6, 12圓環組成。G8-10-B (3)於C-7, C-8 有環內雙鍵，C-6 為醇基取代，在C-10 存在hemiacetal，並與C-20 以氧橋的方式連結，C-11, C-12 間則帶有epoxide ring，另外C-20 則有乙酸酯官能基(acetoxy group)。G8-7-6-A (4)結構與G8-10-B (3)幾乎相同，差別只在C-20 官能基取代為丙烯酯(acrylic ester)。G8-7-5-A (5)與G8-10-B (3)基本構形亦相同，差別只在C-6 為酮基，C-20 為酯基，C-11, C-12 間為環內雙鍵連結。
這五個化合物(1-5)，分別以質譜、紅外線光譜及1D、2D 核磁共
振圖譜分析，以確認結構。

Five new compounds were isolated from the soft coral Cespitularia sp.collected in Green Island, Taiwan. They are G8-7-7-A (1), G8-9-15-30-A(2), G8-10-B (3), G8-7-6-A (4) and G8-7-5-A (5). All of them belong to diterpenes with three methyl groups at C-16, C-17 and C-18, and an
exocyclic double bond between C-4 and C-18.
Compounds 1 and 2 are bicycle norditerpenes. G8-7-7-A (1)
possesses a 6/13 ring and has an endocyclic double bond between C-7 and C-8. It also contains a hydroxyl group at C-6, a ketone group at C-12 and a lactone ring between C-10 and C-11. G8-9-15-30-A (2) is different from 1 at the lactone ring position. The lactone ring of 2 is between C-10 and C-12, and the ketone group is at C-11. So compound 2 possesses a 6/14 bicyclic ring system.
Compounds 3-5 are cespitularin diterpenes, which belong to a 5/6/12 tricyclic ring. They all have an endocyclic double bond between C-7 and C-8. G8-10-B (3) contains an α-hydroxy-β,γ-epoxy-δ-acetoxy furan and a hydroxyl group at C-6. The only difference between compounds 3 and 4 are substiuents at C-20. The C-20 position of 4 is an acrylic group, while compound 3 has an acetoxyl group at C-20. G8-7-5-A (5) contains an γ-hydroxy-α,β-unsaturated-γ-lactone function and a ketone group at C-6. Their structures were elucidated by mass, IR, 1D and 2D NMR spectroscopic analysis.

目錄
頁次
壹、緒論1
一、前言1
二、Cespitularia 屬珊瑚之天然物文獻回顧3
三、研究動機及目的9
貳、軟珊瑚Cespitularia sp. 之化學成分研究10
一、材料採集10
二、軟珊瑚Cespitularia sp. 之分類地位10
三、軟珊瑚Cespitularia sp. 之萃取與分離流程11
四、軟珊瑚Cespitularia sp. 之分離純化流程13
1. G8-7-7-A (1) 之分離純化流程13
2. G8-9-15-30-A (2) 之分離純化流程15
3. G8-10-B (3) 之分離純化流程17
4. G8-7-6-A (4) 之分離純化流程19
5. G8-7-5-A (5) 之分離純化流程21
五、軟珊瑚Cespitularia sp. 雙萜類成分之結構解析23
1. G8-7-7-A (1) 之結構解析23
2. G8-9-15-30-A (2) 之結構解析34
iv
3. G8-10-B (3) 之結構解析45
4. G8-7-6-A (4) 之結構解析55
5. G8-7-5-A (5) 之結構解析64
參、結論74
肆、參考文獻78
伍、附錄－儀器及材料84

圖目錄
頁次
流程圖一、軟珊瑚Cespitularia sp. 之分離流程12
圖一、化合物1 之光譜資料圖24
圖二、化合物1 之NOESY 立體圖26
圖三、G8-7-7-A (1) 之1H-NMR 圖譜28
圖四、G8-7-7-A (1) 之13C-NMR 及DEPT 圖譜29
圖五、G8-7-7-A (1) 之HMQC 圖譜30
圖六、G8-7-7-A (1) 之HMBC 圖譜31
圖七、G8-7-7-A (1) 之COSY 圖譜32
圖八、G8-7-7-A (1) 之NOESY 圖譜33
圖九、化合物2 之光譜資料圖35
圖十、化合物2 之NOESY 立體圖36
圖十一、G8-9-15-30-A (2) 之1H-NMR 圖譜38
圖十二、G8-9-15-30-A (2) 之13C-NMR 及DEPT 圖譜39
圖十三、G8-9-15-30-A (2) 之HMQC 圖譜40
圖十四、G8-9-15-30-A (2) 之HMBC 圖譜41
圖十五、G8-9-15-30-A (2) 之COSY 圖譜42
圖十六、G8-9-15-30-A (2) 之NOESY 圖譜43
圖十七、化合物3 之光譜資料圖46
圖十八、化合物3 之NOESY 立體圖48
圖十九、G8-10-B (3) 之1H-NMR 圖譜49
圖二十、G8-10-B (3) 之13C-NMR圖譜50
圖二十一、G8-10-B (3) 之HMQC 圖譜51
圖二十二、G8-10-B (3) 之HMBC 圖譜52
圖二十三、G8-10-B (3) 之COSY 圖譜53
圖二十四、G8-10-B (3) 之NOESY 圖譜54
圖二十五、化合物4 之光譜資料圖56
圖二十六、化合物4 之NOESY 立體圖57
圖二十七、G8-7-6-A (4) 之1H-NMR 圖譜58
圖二十八、G8-7-6-A (4) 之13C-NMR圖譜59
圖二十九、G8-7-6-A (4) 之HMQC 圖譜60
圖三十、G8-7-6-A (4) 之HMBC 圖譜61
圖三十一、G8-7-6-A (4) 之COSY 圖譜62
圖三十二、G8-7-6-A (4) 之NOESY 圖譜63
圖三十三、化合物5 之光譜資料圖65
圖三十四、化合物5 之NOESY 立體圖66
圖三十五、G8-7-5-A (5) 之1H-NMR 圖譜67
圖三十六、G8-7-5-A (5) 之13C-NMR 及DEPT 圖譜68
圖三十七、G8-7-5-A (5) 之HMQC 圖譜69
圖三十八、G8-7-5-A (5) 之HMBC 圖譜70
圖三十九、G8-7-5-A (5) 之COSY 圖譜71
圖四十、G8-7-5-A (5) 之NOESY 圖譜72
圖四十一、化合物1-5 之可能生合成路徑76

表目錄
頁次
表一、G8-7-7-A (1) 之1H-、13C- NMR dataa、HMBC及
COSY 關連14
表二、G8-9-15-30-A (2) 之1H-、13C- NMR dataa、HMBC
及COSY 關連16
表三、G8-10-B (3) 之1H-、13C -NMR dataa、HMBC及
COSY 關連18
表四、G8-7-6-A (4) 之1H-、13C -NMR dataa 、HMBC及
COSY關連20
表五、G8-7-5-A (5) 之1H-、13C- NMR dataa、HMBC及
COSY 關連22
表六、G8-7-7-A (1)、G8-9-15-30-A (2) 及cespitulactone A
(33) 之1H-、13C- NMR 數值比較a 44
表七、G8-10-B (3)、G8-7-6-A (4) 及G8-7-5-A (5)
之1H-、13C- NMR數值比較a 73

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