臺灣博碩士論文加值系統

綠島產肥厚肉質軟珊瑚 (Sarcophyton crassocaule) 之二氯甲烷萃取物分離純化後，共得到三個diterpenoid化合物，分別為：(1S*, 3R*, 4R*, 7E, 11E, 14R*)-3, 4-epoxycembra-7, 11, 15-trien-1, 14-olide (1)、(1R*, 3E, 7E,11R*, 12S*, 14R*)-11, 12-epoxycembra-3, 7, 15-trien-1, 14-olide (2)、(1R*, 2S*, 3E, 7S*, 8R*, 11S*, 12Z)-8, 11-epidioxy-7-acetoxycembra-3, 12,　15-trien-1, 2-olide (3)，以及二個steroid化合物，分別為：(24S)-24-methylcholestane-3b, 5a, 6b-triol (4) 與24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5)。其中化合物1與2是新化合物，而化合物3為海洋天然物少見之含cyclic peroxide化合物。
綠島產美麗肉質 (S. elegans) 及花環肉質 (S. trocheliophorum) 軟珊瑚之二氯甲烷萃取物分離純化後，從美麗肉質軟珊瑚中分離到24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) 之steroid化合物，從花環肉質軟珊瑚中分離到 (+)-isosarcophine (6) 之diterpenoid化合物。
另外，由未知屬名之八放珊瑚 (編號CD01) 中，共分離到二個steroid化合物，分別為：cholesterol (7) 及 (22E, 24S)-24-methylcholesta- 5, 22-dien-3b-ol (8)。
上述之化合物經癌細胞毒殺活性測試後，化合物1-4、6及7對P388具有選擇性抑制作用，而化合物2和5則對HT-29有選擇性抑制。

Chromatographic purification of a methylene chloride extract of Formosan soft coral Sarcophyton crassocaule (collected in Green island) led to the isolation of two new (1S*, 3R*, 4R*, 7E, 11E, 14R*)-3, 4-epoxycembra-7, 11, 15-trien-1, 14-olide (1) and (1R*, 3E, 7E,11R*, 12S*, 14R*)-11, 12-epoxycembra-3, 7, 15-trien-1, 14-olide (2) isomeric diterpenoids , a known cyclic peroxide diterpenoid (1R*, 2S*, 3E, 7S*, 8R*, 11S*, 12Z)-8, 11-epidioxy-7-acetoxycembra-3, 12, 15-trien-1, 2-olide (3), as well as two known (24S)-24-methylcholestane-3b, 5a, 6b-triol (4) and 24x-methyl-cholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) steroids.
Chromatographic fractionation of a methylene chloride extract of two Formosan soft corals Sarcophyton elegans (collected in Green island) led to the isolation of a known 24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) steroid, the methylene chloride extract of Sarcophyton trocheliophorum, on the other hand, afforded a known diterpenoid, (+)-isosarcophine (6).
Purification of a methylene chloride extract of Octocorallia soft coral (unidentified) led to the isolation of two known steroids, cholesterol (7) and (22E, 24S)-24-methylcholesta-5, 22-dien-3b-ol (8).
Compounds 1-7 exhibited cytotoxicity against P388 cancer cell line. Compounds 2 and 5 were active against HT-29 cancer cell line.

壹、緒論…………………………………………………………………12
一、 前言…………………………………………………………12
二、 曾由Sarcophyton屬軟珊瑚中分離到之化合物……………　　　　　14
三、 過去由Sarcophyton屬軟珊瑚所分離到之有生物活性二次代謝物………………………………………………………25
四、 研究動機及目的……………………………………………26
貳、Sarcophyton crassocaule軟珊瑚化學成分之研究………………27
一、 採集及分類地位……………………………………………27
二、 Sarcophyton crassocaule軟珊瑚之萃取與分離…………28
三、 Sarcophyton crassocaule軟珊瑚化學成分之分離純化……31
(1) GN26-203 (1) 之分離純化…………………………….31
(2) GN26-204 (2) 之分離純化………………………………33
(3) GN26-206 (3) 之分離純化………………………………35
(4) GN26-16K (4) 之分離純化……………………………37
四、 Sarcophyton crassocaule軟珊瑚化學成分之結構解析……40
(1) GN26-203 (1) 之結構解析………………………………40
(2) GN26-204 (2) 之結構解析………………………………52
(3) GN26-206 (3) 之結構解析………………………………63
(4) GN26-16K (4) 之結構解析……………………………74
參、Sarcophyton elegans軟珊瑚化學成分之研究……………………79
一、 採集及分類地位……………………………………………79
二、 Sarcophyton elegans軟珊瑚之萃取與分離…………………80
三、 Sarcophyton elegans軟珊瑚化學成分之分離純化………….82
(1) GN07-53K (5) 之分離純化……………………………..82
四、 Sarcophyton elegans軟珊瑚化學成分之結構解析…………85
(1) GN07-53K (5) 之結構解析……………………………85
肆、Sarcophyton trocheliophorum軟珊瑚化學成分之研究……………90
一、 採集及分類地位……………………………………………90
二、 Sarcophyton trocheliophorum軟珊瑚之萃取與分離………91
三、 Sarcophyton trocheliophorum軟珊瑚化學成分之分離純化…………………………………………………………….93
(1) GN11-97 (6) 之分離純化………………………………93
四、 Sarcophyton trocheliophorum軟珊瑚化學成分之結構解析……………………………………………………………95
(1) GN11-97 (6) 之結構解析………………………………..95
伍、編號CD01八放珊瑚化學成分之研究……………………………99
一、 採集及分類地位……………………………………………..99
二、 編號CD01八放珊瑚之萃取與分離………………………100
三、 編號CD01八放珊瑚化學成分之分離純化……………….102
(1) CD01-104K (7) 之分離純化……………………………102
(2) CD01-106K (8) 之分離純化……………………………104
四、 編號CD01八放珊瑚化學成分之結構解析………………107
(1) CD01-104K (7) 之結構解析……………………………107
(2) CD01-106K (8) 之結構解析……………………………111
陸、化合物之癌細胞毒殺活性………………………………………115
柒、結論………………………………………………………………116
捌、參考文獻…………………………………………………………118
玖、附錄………………………………………………………………127
一、 使用儀器及藥品……………………………………………127
二、 癌細胞毒殺活性測試之分析方法…………………………129
三、 MTT分析原理……………………………………………130






圖目錄
頁次
圖一、本研究所分離到之成分…………………………………………3
圖二、Sarcophyton crassocaule軟珊瑚所分離到之化學成分………29
圖三、Sarcophyton crassocaule軟珊瑚之分離流程………………….. 30
圖四、GN26-203 (1) 之1H-NMR圖譜…………………………………44
圖五、GN26-203 (1) 之13C-NMR及DEPT圖譜……………………45
圖六、GN26-203 (1) 之HMQC圖譜…………………………………46
圖七、GN26-203 (1) 之COSY圖譜……………………………………47
圖八、GN26-203 (1) 之HMBC圖譜…………………………………...48
圖九、GN26-203 (1) 之HMBC關聯圖………………………………...49
圖十、GN26-203 (1) 之NOESY圖譜…………………………………50
圖十一、GN26-203 (1) 之NOESY關聯圖……………………………51
圖十二、GN26-204 (2) 之1H-NMR圖譜………………………………55
圖十三、GN26-204 (2) 之13C-NMR及DEPT圖譜……………………56
圖十四、GN26-204 (2) 之HMQC圖譜………………………………..57
圖十五、GN26-204 (2) 之COSY圖譜…………………………………58
圖十六、GN26-204 (2) 之HMBC圖譜………………………………59
圖十七、GN26-204 (2) 之HMBC關聯圖……………………………60
圖十八、GN26-204 (2) 之NOESY圖譜………………………………61
圖十九、GN26-204 (2) 之NOESY關聯圖……………………………62
圖二十、GN26-206 (3) 之1H-NMR圖譜………………………………66
圖二十一、GN26-206 (3) 之13C-NMR及DEPT圖譜…………………67
圖二十二、GN26-206 (3) 之HMQC圖譜…………………………….68
圖二十三、GN26-206 (3) 之COSY圖譜………………………………69
圖二十四、GN26-206 (3) 之HMBC圖譜………………………….…70
圖二十五、GN26-206 (3) 之HMBC關聯圖……………………….…71
圖二十六、GN26-206 (3) 之NOESY圖譜………………………….…72
圖二十七、GN26-206 (3) 之NOESY關聯圖…………………………73
圖二十八、GN26-16K (4) 之1H-NMR圖譜………………………….76
圖二十九、GN26-16K (4) 之13C-NMR及DEPT圖譜…………….…77
圖三十、Sarcophyton elegans軟珊瑚所分離到之化學成分………….80
圖三十一、Sarcophyton elegans軟珊瑚之分離流程………………….81
圖三十二、GN07-53K (5) 之1H-NMR圖譜…………………………87
圖三十三、GN26-18K (5) 之1H-NMR圖譜……………………….…88
圖三十四、GN07-53K (5) 之13C-NMR及DEPT圖譜………………89
圖三十五、Sarcophyton trocheliophorum軟珊瑚所分離到之化學成分………………………………………………………….91
圖三十六、Sarcophyton trocheliophorum軟珊瑚之分離流程………..92
圖三十七、GN11-97 (6) 之1H-NMR圖譜……………………………..97
圖三十八、GN11-97 (6) 之13C-NMR及DEPT圖譜…………………..98
圖三十九、編號CD01八放珊瑚所分離到之化學成分…………100
圖四十、編號CD01八放珊瑚之分離流程……………………….101
圖四十一、CD01-104K (7) 之1H-NMR圖譜………………………109
圖四十二、CD01-104K (7) 之13C-NMR及DEPT圖譜……………110
圖四十三、CD01-106K (8) 之1H-NMR圖譜………………………113
圖四十四、CD01-106K (8) 之13C-NMR及DEPT圖譜……………114














表目錄
頁次
表一、曾由Sarcophyton屬分離到之Cembranoids…………………….14表二、曾由Sarcophyton屬分離到之Steroids………………………….17
表三、化合物4及文獻之13C-NMR化學位移表……………………78
表四、化合物1-8之癌細胞毒殺活性值………………………115

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