針對台灣墾丁南灣所採集的軟珊瑚 Sinularia facile 所具有之化學成分研究中，我們共分離得到10個二次代謝產物，有4個cembranoid天然化合物及6個固醇類天然化合物；其中包含2個新的cembranoid天然化合物分別為 (3E,7E,11E,15E)-cembra-3,7,11,15-tetraen-1-ol (1) 和 (1R*,12R*,3E, 7E,10E, 15E)-cembra-3,7,10,15-tetraen-12-ol (2)，及2個已知的cembranoid天然化合物分別為diepoxycembrene A (3) 和isocembrol A (4)，另外分離到5個新發現固醇類天然化合物，分別為cholest-5-ene-1α,3β-diol-11α-monoacetate (5)、cholesta-5,24-diene-1α, 3β-diol-11α- monoacetate (6)、cholesta-5,24-diene-1α,3β-11α-triol (7)、24- methylenecholesta-5-ene-1α,3β-diol-11α,18-diacetate (8)、24(S)- methylcholest-5-ene-1α,3β-diol-11α-monoacetate (9)，及1個已知的固醇類天然化合物為24-methylenecholest-5-ene-1α,3β,11α- triol (10)。這些化合物的化學結構及相對立體構型均是以各種光譜解析 (1D NMR、2D NMR、IR、MS) 及比對文獻上類似的化合物而予以確定。並將所獲得之天然化合物進行癌細胞株的抑制活性測試。

Our chemical investigation on the soft coral Sinularia facile which was collected off the coast of Kengting, Taiwan, has led to the isolation of ten metabolites 1－10, including four cembranoids and six polyhydroxylated steroids. Cembranoids isolated are two new natural compounds, (3E,7E,11E,15E)-cembra-3,7,11,15-tetraen-1-ol (1) and (1R*,12R*,3E,7E,10E,15E)-cembra-3,7,10,15-tetraen-12-ol (2), and two known compounds diepoxycembrene A (3) and isocembrol A (4). Moreover, five new polyhydroxylated steroids, cholest-5-ene-1α,3β-diol- 11α-monoacetate (5), cholesta-5,24-diene-1α,3β -diol-11α-monoacetate (6), cholesta-5,24-diene-1α,3β-11α-triol (7), 24- methylenecholesta-5-ene-1α, 3β-diol-11α,18-diacetate (8) and 24(S)- methylcholest-5-ene-1α,3β-diol- 11α-monoacetate (9), and one known compound, 24-methylenecholest-5- ene-1α,3β,11α-triol (10). The chemical structures of these compounds (1－10) were elucidated by spectroscopic evidences (IR, MS, 1D NMR, and 2D NMR) and by comparison of the spectral data of these compounds in the literature. Cytotoxicity of these compounds toward various cancer cell lines has also been determined.

目錄
頁次
中文摘要 1
英文摘要 2
化合物結構 3
壹、緒論
一、前言 4
二、研究動機 5
三、文獻回顧 6
貳、實驗程序與方法
一、生物樣品採集時間、地點與分類地位 19
二、生物樣品的分類 19
三、萃取與分離純化步驟 20
四、實驗器材與溶劑
(一) 儀器 23
(二) 試劑藥品 24
參、細胞毒殺活性測試
一、生物活性試驗 25
(一)細胞活性測試之檢測原理
二、實驗採用之癌細胞株 26
肆、實驗結果與討論
一、簡易指形軟珊瑚Sinularia facile化合物之結構解析
(一) (1S*,3E,7E,11E,15E)-Cembra-3,7,11,15-tetraen-1-ol (1)之結構解析 27
(二) (1R*,12R*,3E,7E,10E,15E)-Cembra-3,7,10,15-tetraen-12-ol (2)之結構解析 40
(三) Diepoxycembrene A (3)之結構解析 53
(四) Isocembrol A (4)之結構解析 66
(五) Cholesta-5-ene-1α,3β-diol-11α-monoacetate (5)之結構解析 76
(六) Cholesta-5,24-diene-1α,3β-diol-11α-monoacetate (6)之結構解析 89
(七) Cholesta-5,24-diene-1α,3β-11α-triol (7)之結構解析 102
(八) 24-Methylenecholesta-5-ene-1α,3β-diol-11α,18-diacetate (8)之結構解析 115
(九) 24(S)-Methylcholesta-5-ene-1α,3β-diol-11α-monoacetate (9)之結構解析 128
(十) 24-Methylenecholest-5-ene-1α,3β,11α-triol (10)之結構解析 142
二、實驗數據整理 146
三、天然化合物之活性 149
伍、結論 150
陸、參考文獻 152


















圖目錄
頁次
Figure 2-2-1. 簡易指形軟珊瑚Sinularia facile之分離流程 (I) 22
Figure 4-1-3. 化合物1之1H-NMR圖譜 31
Figure 4-1-4. 化合物1之13C-NMR圖譜 32
Figure 4-1-5. 化合物1之DEPT圖譜 33
Figure 4-1-6. 化合物1之HMQC圖譜 34
Figure 4-1-7. 化合物1之HMBC圖譜 35
Figure 4-1-8. 化合物1之COSY圖譜 36
Figure 4-1-9. 化合物1之NOESY圖譜 37
Figure 4-1-10. 化合物1之低解析ESIMS圖譜 38
Figure 4-1-11. 化合物1之高解析ESIMS圖譜 39
Figure 4-2-3. 化合物2之1H-NMR圖譜 44
Figure 4-2-4. 化合物2之13C-NMR圖譜 45
Figure 4-2-5. 化合物2之DEPT圖譜 46
Figure 4-2-6. 化合物2之HMQC 47
Figure 4-2-7. 化合物2之HMBC圖譜 48
Figure 4-2-8. 化合物2之COSY圖譜 49
Figure 4-2-9. 化合物2之NOESY圖譜 50
Figure 4-2-10. 化合物2之低解析ESIMS圖譜 51
Figure 4-2-11. 化合物2之高解析ESIMS圖譜 52
Figure 4-3-3. 化合物3之1H-NMR圖譜 57
Figure 4-3-4. 化合物3之13C-NMR圖譜 58
Figure 4-3-5. 化合物3之DEPT圖譜 59
Figure 4-3-6. 化合物3之HMQC圖譜 60
Figure 4-3-7. 化合物3之HMBC圖譜 61
Figure 4-3-8. 化合物3之COSY圖譜 62
Figure 4-3-9. 化合物3之NOESY圖譜 63
Figure 4-3-10. 化合物3之低解析ESIMS圖譜 64
Figure 4-3-11. 化合物3之高解析ESIMS圖譜 65
Figure 4-4-2. 化合物4之1H-NMR圖譜 69
Figure 4-4-3. 化合物4之13C-NMR圖譜 70
Figure 4-4-4. 化合物4之DEPT圖譜 71
Figure 4-4-5. 化合物4之HMQC圖譜 72
Figure 4-4-6. 化合物4之HMBC圖譜 73
Figure 4-4-7. 化合物4之COSY圖譜 74
Figure 4-4-8. 化合物4之低解析ESIMS圖譜 75
Figure 4-5-3. 化合物5之1H-NMR圖譜 80
Figure 4-5-4. 化合物5之13C-NMR圖譜 81
Figure 4-5-5. 化合物5之DEPT圖譜 82
Figure 4-5-6. 化合物5之HMQC圖譜 83
Figure 4-5-7. 化合物5之HMBC圖譜 84
Figure 4-5-8. 化合物5之COSY圖譜 85
Figure 4-5-9. 化合物5之NOESY圖譜 86
Figure 4-5-10. 化合物5之低解析ESIMS圖譜 87
Figure 4-5-11. 化合物5之高解析ESIMS圖譜 88
Figure 4-6-3. 化合物6之1H-NMR圖譜 93
Figure 4-6-4. 化合物6之13C-NMR圖譜 94
Figure 4-6-5. 化合物6之DEPT圖譜 95
Figure 4-6-6. 化合物6之HMQC圖譜 96
Figure 4-6-7. 化合物6之HMBC圖譜 97
Figure 4-6-8. 化合物6之COSY圖譜 98
Figure 4-6-9. 化合物6之NOESY圖譜 99
Figure 4-6-10. 化合物6之低解析ESIMS圖譜 100
Figure 4-6-11. 化合物6之高解析ESIMS圖譜 101
Figure 4-7-3. 化合物7之1H-NMR圖譜 106
Figure 4-7-4. 化合物7之13C-NMR圖譜 107
Figure 4-7-5. 化合物7之DEPT圖譜 108
Figure 4-7-6. 化合物7之HMQC圖譜 109
Figure 4-7-7. 化合物7之HMBC圖譜 110
Figure 4-7-8. 化合物7之COSY圖譜 111
Figure 4-7-9. 化合物7之NOESY圖譜 112
Figure 4-7-10. 化合物7之低解析ESIMS圖譜 113
Figure 4-7-11. 化合物7之高解析ESIMS圖譜 114
Figure 4-8-3. 化合物8之1 H-NMR圖譜 119
Figure 4-8-4. 化合物8之13 C-NMR圖譜 120
Figure 4-8-5. 化合物8之DEPT圖譜 121
Figure 4-8-6. 化合物8之HMQC圖譜 122
Figure 4-8-7. 化合物8之HMBC圖譜 123
Figure 4-8-8. 化合物8之COSY圖譜 124
Figure 4-8-9. 化合物8之NOESY圖譜 125
Figure 4-8-10. 化合物8之低解析ESIMS圖譜 126
Figure 4-8-11. 化合物8之高解析ESIMS圖譜 127
Figure 4-9-3. 化合物9之1H-NMR圖譜 133
Figure 4-9-4. 化合物9之13C-NMR圖譜 134
Figure 4-9-5. 化合物9之DEPT圖譜 135
Figure 4-9-6. 化合物9之HMQC圖譜 136
Figure 4-9-7. 化合物9之HMBC圖譜 137
Figure 4-9-8. 化合物9之COSY圖譜 138
Figure 4-9-9. 化合物9之NOESY圖譜 139
Figure 4-9-10. 化合物9之低解析ESIMS圖譜 140
Figure 4-9-10. 化合物9之高解析ESIMS圖譜 141
Figure 4-10-1. 化合物10之1H-NMR圖譜 143
Figure 4-10-2. 化合物10之13C-NMR圖譜 144
Figure 4-10-3. 化合物10之低解析ESIMS圖譜 145




表目錄
頁次
Table 1-1. Cembranoids from the soft carol S. flexibilis. 7
Table 1-2. Cembranoids from the soft carol S. gibberosa. 8
Table 1-3. Cembranoids from the soft carol S. mayi. 9
Table 1-4. Cembranoids from the soft carol S. microclavata. 10
Table 1-5. Cembranoids from the soft carol S. capillosa. 12
Table 1-6. Cembranoids from the soft carol S. dissecta. 13
Table 4-1-1.
Table 4-2-1. 1H and 13C NMR data of 1
1H and 13C NMR data of 2 30
43
Table 4-3-1. 1H and 13C NMR data of 3 56
Table 4-4-1. 1H and 13C NMR data of 4 68
Table 4-5-1. 1H and 13C NMR data of 5 79
Table 4-6-1. 1H and 13C NMR data of 6 92
Table 4-7-1. 1H and 13C NMR data of 7 105
Table 4-8-1. 1H and 13C NMR data of 8 118
Table 4-9-1. 化合物與已知steroids的支鏈13 C-NMR比較表 131
Table 4-9-1. 1H and 13C NMR data of 9 132
Table 4-3. Cytotoxicities of compounds 1－10 149

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