本次研究是從基翬漁港所採集的軟珊瑚Sarcophyton glaucum, 並使用乙酸乙酯進行萃取。從萃取物中所含的天然物進行純化後，共得到十六個化合物，包括5個新的化合物1−5 : 1β,15β-epoxy-16-deoxysarcophine (1), glaucumolide A (2), 4-epi-crassumol A (3), isolobocrasol (4), (23R,24R,17Z)-23,24-dimethylclolest- 17(20)-en-3β,5α,6β,11α,16α-pentaol (5)以及十一個已知的化合物 6−16。化合物1−16的化學結構建立是利用(1D and, 2D NMR, IR and MS)等光譜分析,並且比對文獻。
在細胞毒殺活性測試方面，化合物 1−7, 9−12, 14−16針對HepG2 (人類肝癌細胞)、MDA-MB-231 (人類乳腺癌細胞) 以及 A549 (人類肺腺癌細胞)三種癌細胞株進行毒殺活性測試。其中化合物14針對HepG2、MDA-MB-231以及A549三種癌細胞株具有抑制活性，其IC50值分別為9.75、14.07 以及15.87 μg/mL。在抗發炎活性測試的部分，化合物13, 14具有相當好的NO抑制率。

In the investigation of the Formsoan soft coral Sarcophyton glaucum, collected from the Jihui Fish Port, we have studied the chemical constituents of the ethyl acetate extract from the soft coral Sarcophyton glaucum. This study has led to the isolation of sixteen compounds, including five new compounds 1β,15β-epoxy-16-
deoxysarcophine (1), glaucumolide A (2), 4-epi-crassumol A (3), isolobocrasol (4), (23R,24R,17Z)-23,24-dimethylclolest-17(20)-en-3β,5α,6β,11α,16α-pentaol (5) and eleven known compounds 6−16. The chemical structures of compounds 1−16 were established by spectral analysis (1D and, 2D NMR, IR and MS) and by comparison of the spectral data with those of related known compounds.
The cytotoxicity of compounds 1−7, 9−12, 14−16 against the three human cancer cell lines, HepG2 (human hepatocellular liver carcinoma), MDA-MB-231 (human breast adenocarcinoma) and A549 (human lung epithelial cells) was evaluated, compound 14 showed the moderate cytotoxicity against the human cancer cell lines HepG2, MDA-MB-231 and A-549 with IC50 values of 9.75, 14.07 and 15.87 μg/mL, respectively. On the part of anti-inflammation assay, compound 13, 14 showed effectively inhibiting activity against NO at 40 μg/mL.

論文審定書 i
謝詞 ii
中文摘要 iii
英文摘要 iv
化合物1−16的化學結構 v
第一章、緒論 1
第一節、前言 1
第二節、研究動機與目的 2
第三節、文獻回顧 4
第二章、生物材料與研究方法 25
第一節、Sarcophyton glaucum的採集時間與地點 25
第二節、Sarcophyton glaucum的分類地位 25
第三節、Sarcophyton glaucum的萃取與分離純化流程 26
第四節、實驗儀器與材料 29
實驗儀器 29
實驗材料 29
第三章、實驗結果與結構解析 31
第一節、軟珊瑚Sarcophyton glaucum之化學結構的結構解析 31
(一)、1β,15β-Epoxy-16-deoxysarcophine (1) 結構解析 31
(二)、Glaucumolide A (2) 結構解析 43
(三)、4-epi-Crassumol A (3) 結構解析 55
(四)、Isolobocrasol (4) 結構解析 67
(五)、(23R,24R,17Z)-23,24-Dimethylclolest-17(20)-
en-3β,5α,6β,11α,16α-pentaol (5) 結構解析 79
(六)、Sarcophine (6) 結構解析 93
(七)、(+)-Polydactylide (7) 結構解析 97
(八)、7β,8β-Epoxy-4α-hydroxycembra-
1(15),2,11-trien-16,2-olide (8) 結構解析 101
(九)、7β,8β-Epoxy-4β-hydroxycembra-
1(15),2,11-trien-16,2-olide (9) 結構解析 105
(十)、Crassumol A (10) 結構解析 109
(十一)、Sarcophyolide E (11) 結構解析 113
(十二)、Lobocrasol (12) 結構解析 117
(十三)、Sarcomilasterol (13) 結構解析 123
(十四)、Sarcoaldesterol B (14) 結構解析 127
(十五)、Sarglaucsterol (15) 結構解析 131
(十六)、Pubinernoid A (16) 結構解析 135
第二節、化合物的物理性質與數據整理 139
第四章、生物活性 142
第一節、細胞毒殺活性之測試 142
第二節、細胞毒殺活性之實驗結果 144
第三節、抗發炎活性測試 146
第四節、抗發炎之實驗結果 147
第五章、結論 151
第六章、參考文獻 153
Figure 2-1 Sarcophyton glaucum 25
Figure 2-2 Sarcophyton glaucum的分離流程圖 28
Figure 3-1-1 1H-1H COSY and HMBC correlations of 1 32
Figure 3-1-2 NOESY correlations of 1 35
Figure 3-1-3 IR spectrum of 1 37
Figure 3-1-4 ESI mass spectrum of 1 37
Figure 3-1-5 HRESI mass spectrum of 1 38
Figure 3-1-6 1H-NMR spectrum of 1 39
Figure 3-1-7 1H-NMR spectrum of 1 (局部放大圖) 39
Figure 3-1-8 13C-NMR spectrum of 1 40
Figure 3-1-9 DEPT spectrum of 1 40
Figure 3-1-10 HMQC spectrum of 1 41
Figure 3-1-11 1H-1H COSY spectrum of 1 41
Figure 3-1-12 HMBC spectrum of 1 42
Figure 3-1-13 NOESY spectrum of 1 42
Figure 3-2-1 1H-1H COSY and HMBC correlations of 2 44
Figure 3-2-2 NOESY correlations of 2 47
Figure 3-2-3 IR spectrum of 2 49
Figure 3-2-4 ESI mass spectrum of 2 49
Figure 3-2-5 HRESI mass spectrum of 2 50
Figure 3-2-6 1H-NMR spectrum of 2 51
Figure 3-2-7 1H-NMR spectrum of 2 (局部放大圖) 51
Figure 3-2-8 13C-NMR spectrum of 2 52
Figure 3-2-9 DEPT spectrum of 2 52
Figure 3-2-10 HMQC spectrum of 2 53
Figure 3-2-11 1H-1H COSY spectrum of 2 53
Figure 3-2-12 HMBC spectrum of 2 54
Figure 3-2-13 NOESY spectrum of 2 54
Figure 3-3-1 1H-1H COSY and HMBC correlations of 3 56
Figure 3-3-2 NOESY correlations of 3 59
Figure 3-3-3 IR spectrum of 3 61
Figure 3-3-4 ESI mass spectrum of 3 61
Figure 3-3-5 HRESI mass spectrum of 3 62
Figure 3-3-6 1H-NMR spectrum of 3 63
Figure 3-3-7 1H-NMR spectrum of 3 (局部放大圖) 63
Figure 3-3-8 13C-NMR spectrum of 3 64
Figure 3-3-9 DEPT spectrum of 3 64
Figure 3-3-10 HMQC spectrum of 3 65
Figure 3-3-11 1H-1H COSY spectrum of 3 65
Figure 3-3-12 HMBC spectrum of 3 66
Figure 3-3-13 NOESY spectrum of 3 66
Figure 3-4-1 1H-1H COSY and HMBC correlations of 4 68
Figure 3-4-2 NOESY correlations of 4 71
Figure 3-4-3 IR spectrum of 4 73
Figure 3-4-4 ESI mass spectrum of 4 73
Figure 3-4-5 HRESI mass spectrum of 4 74
Figure 3-4-6 1H-NMR spectrum of 4 75
Figure 3-4-7 1H-NMR spectrum of 4 (局部放大圖) 75
Figure 3-4-8 13C-NMR spectrum of 4 76
Figure 3-4-9 DEPT spectrum of 4 76
Figure 3-4-10 HMQC spectrum of4 77
Figure 3-4-11 1H-1H COSY spectrum of 4 77
Figure 3-4-12 HMBC spectrum of 4 78
Figure 3-4-13 NOESY spectrum of 4 78
Figure 3-5-1 1H-1H COSY and HMBC correlations of 5 80
Figure 3-5-2 NOESY correlations of 5 84
Figure 3-5-3 IR spectrum of 5 87
Figure 3-5-4 ESI mass spectrum of 5 87
Figure 3-5-5 HRESI mass spectrum of 5 88
Figure 3-5-6 1H-NMR spectrum of 5 89
Figure 3-5-7 1H-NMR spectrum of 5 (局部放大圖) 89
Figure 3-5-8 13C-NMR spectrum of 5 90
Figure 3-5-9 DEPT spectrum of 5 90
Figure 3-5-10 HMQC spectrum of 5 91
Figure 3-5-11 1H-1H COSY spectrum of 5 91
Figure 3-5-12 HMBC spectrum of 5 92
Figure 3-5-13 NOESY spectrum of 5 92
Figure 3-6-1 ESI mass spectrum of 6 95
Figure 3-6-2 1H-NMR spectrum of 6 95
Figure 3-6-3 13C-NMR spectrum of 6 96
Figure 3-7-1 ESI mass spectrum of 7 99
Figure 3-7-2 1H-NMR spectrum of 7 100
Figure 3-7-3 13C-NMR spectrum of 7 100
Figure 3-8-1 ESI mass spectrum of 8 103
Figure 3-8-2 1H-NMR spectrum of 8 104
Figure 3-8-3 13C-NMR spectrum of 8 104
Figure 3-9-1 ESI mass spectrum of 9 107
Figure 3-9-2 1H-NMR spectrum of 9 108
Figure 3-9-3 13C-NMR spectrum of 9 108
Figure 3-10-1 ESI mass spectrum of 10 111
Figure 3-10-2 1H-NMR spectrum of 10 112
Figure 3-10-3 13C-NMR spectrum of 10 112
Figure 3-11-1 ESI mass spectrum of 11 115
Figure 3-11-2 1H-NMR spectrum of 11 116
Figure 3-11-3 13C-NMR spectrum of 11 116
Figure 3-12-1 NOESY correlations of 12 118
Figure 3-12-2 ESI mass spectrum of 12 121
Figure 3-12-3 1H-NMR spectrum of 12 121
Figure 3-12-4 13C-NMR spectrum of 12 122
Figure 3-12-5. NOESY spectrum of 12 122
Figure 3-13-1 ESI mass spectrum of 13 125
Figure 3-13-2 1H-NMR spectrum of 13 126
Figure 3-13-3 13C-NMR spectrum of 13 126
Figure 3-14-1 ESI mass spectrum of 14 129
Figure 3-14-2 1H-NMR spectrum of 14 130
Figure 3-14-3 13C-NMR spectrum of 14 130
Figure 3-15-1 ESI mass spectrum of 15 133
Figure 3-15-2 1H-NMR spectrum of 15 134
Figure 3-15-3 13C-NMR spectrum of 15 134
Figure 3-16-1 ESI mass spectrum of 16 137
Figure 3-16-2 1H-NMR spectrum of 16 138
Figure 3-16-3 13C-NMR spectrum of 16 138
Table 1-1.軟珊瑚Sarcophyton glaucum所含cembrane類之文獻回顧 5
Table 1-2.軟珊瑚Sarcophyton glaucum所含biscembrane類之文獻回顧 17
Table 1-3.軟珊瑚Sarcophyton glaucum所含steroid類之文獻回顧 20
Table 3-1. 1H and 13C NMR data,1H-1H COSY, and HMBC correlations of 1 36
Table 3-2. 1H and 13C NMR data,1H-1H COSY, and HMBC correlations of 2 48
Table 3-3. 1H and 13C NMR data,1H-1H COSY, and HMBC correlations of 3 60
Table 3-4. 1H and 13C NMR data,1H-1H COSY, and HMBC correlations of 4 72
Table 3-5. 1H and 13C NMR data,1H-1H COSY, and HMBC correlations of 5 85
Table 3-6. 1H-NMR and 13C-NMR data of 6 94
Table 3-7. 1H-NMR and 13C-NMR data of 7 98
Table 3-8. 1H-NMR and 13C-NMR data of 8 102
Table 3-9. 1H-NMR and 13C-NMR data of 9 106
Table 3-10. 1H-NMR and 13C-NMR data of 10 110
Table 3-11. 1H-NMR and 13C-NMR data of 11 114
Table 3-12. 1H-NMR and 13C-NMR data of 12 120
Table 3-13. 1H-NMR and 13C-NMR data of 13 124
Table 3-14. 1H-NMR and 13C-NMR data of 14 128
Table 3-15. 1H-NMR and 13C-NMR data of 15 132
Table 3-16. 1H-NMR and 13C-NMR data of 16 136
Table 4-1. 化合物1−7、9−12、14−16針對HepG2、MDA-MB-231、A-549 144
細胞毒殺活性之實驗數據
Table 4-2. 化合物6、8、9、13針對Molt 4、U 937、SUP-T1細胞毒殺活
性之實驗數據 145
Table 4-3. 化合物1−7、9−16 (2.5 μg/mL) 抗發炎活性之實驗數據 147
Table 4-4. 化合物1−7、9−16 (5 μg/mL) 抗發炎活性之實驗數據 148
Table 4-5. 化合物1−7、9−16 (20 μg/mL) 抗發炎活性之實驗數據 149
Table 4-6. 化合物1−7、9−16 (40 μg/mL) 抗發炎活性之實驗數據 150

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