以往天然物學者報導台灣產竹珊瑚 Isis hippuris 之二次代謝物研究，其採集地點皆為綠島海域。為了尋找其他具有生物活性的新化合物，我們針對蘭嶼海域所採集的竹珊瑚I. hippuris 進行天然物萃取分離，經由各種層析技術之純化，我們分離出11 個新的多氧化態固醇類化合物 (1–11) 以及兩個已知的固醇類化合物 (12 和13)。這些新化合物的結構鑑定是藉由各種光譜分析 (一維及二維NMR、紅外線光譜儀、旋光及高解析質譜儀) 並與已知化合物之文獻比對光譜資料而決定的。化合物1–13 分別對於人類肺癌細胞 (A-549)、人類直腸癌細胞 (HT-29) 與老鼠血癌細胞 (P-388) 進行細胞毒殺活性實驗，發現化合物12 和13 對P-388 皆有毒殺活性，其 ED50 值分別為 3.6 和 3.2 μg/mL，化合物12 則對 A-549 有毒殺活性，ED50值為 3.9 μg/mL。另外化合物1–13 進行抗人類巨細胞病毒 (human cytomegalovirus) 測試，發現化合物8 對人類巨細胞病毒有抑制活性 EC50 2.0 μg/mL。

Previous studies on the secondary metabolites of Formosan octocoral Isis hippuris were collected only at Green Island. In the course of our studies on secondary metabolites from marine organisms, the acetone-solubles of the Formosan octocoral Isis hippuris collected at Orchid Island has led to the isolation of eleven polyoxygenated steroids (1–11), along with two known compounds (12 and 13). The structures of these compounds were determined on the basis of their spectroscopic and physical data, including NMR, IR, MS, etc. The cytotoxicity against of A-549 (human lung epithelial carcinoma), HT-29 (human colon adenocarcinoma), and P-388 (mouse lymphocytic leukemia) cells, and anti-HCMV (human cytomegalovirus) activity of metabolites 1–13 were evaluated. Compounds 12 and 13 displayed cytotoxicity against P-388 cell line with ED50 values of 3.2 and 3.6 μg/mL, respectively. Compound 12 exhibited cytotoxicity against A-549 cell line with an ED50 value of 3.8 μg/mL. Compound 8 exhibit inhibitory activity against HCMV, with EC50 values of 2.0 μg/mL.

目 錄
謝辭iii
中文摘要iv
英文摘要v
化合物1–13 之化學結構 vi
目錄vii
表目錄ix
圖目錄xi
縮寫對照表xx
第一章、緒論1
第二章、Isis hippuris 二次代謝物的文獻回顧 3
2.1. Hippuristerone 類化合物的文獻回顧3
2.2. Hippuristerol 類化合物的文獻回顧6
2.3. Hippuristanol 類化合物的文獻回顧8
2.3.1. C-18 氧化取代的 hippuristanol 類化合物的文獻回顧14
2.4. Gorgosterol 類化合物的文獻回顧18
2.5. Suberosane 類化合物的文獻回顧24
第三章、材料與研究方法26
3.1. 實驗設備儀器26
3.2. 實驗材料28
3.3. Isis hippuris 的採集與分類地位 29
3.4. Isis hippuris 萃取與分離流程 30
第四章、化學成分之結構證明36
4.1. LY19-28-67-11-19 (1) 之結構解析36
4.2. LY19-29-3B2-11 (2) 之結構解析54
4.3. LY19-29-3B2-9 (3) 之結構解析70
4.4. LY19-28-67-11-20 (4) 之結構解析88
4.5. LY19-28-96-75-19A (5) 之結構解析105
4.6. LY19-28-96-18 (6) 之結構解析121
4.7. LY19-28-67-11-16 (7) 之結構解析138
4.8. LY19-39D-A6 (8) 之結構解析156
4.9. LY19-29-3B2-10 (9) 之結構解析173
4.10. LY19-28-96-70-25 (10) 之結構解析191
4.11. LY19-28-75-19B (11) 之結構解析208
4.12. 5β,6β-epoxygorgostane-1α,3β, 11α,12β-tetrol (12) 之結構鑑定224
4.13. Gorgost-5-ene-3β,7α,11α,12β-tetrol 11-acetate (13) 之結構鑑定239
第五章、生物活性試驗249
5.1. 細胞毒殺活性測試249
5.2. MTT 分析原理250
5.3. 細胞毒殺活性試驗結果 251
5.4. 抗 HCMV 病毒的測試252
第六章、結論254
第七章、參考文獻257
第八章、附錄262
電子學位論文永不公開申請書262
紙本學位論文延後公開陳覽申請書263

表目 錄
Table 2.1. Cytotoxicity of 14, 15, 17 and 18 5
Table 2.2. Cytotoxicity of 27–28 and 30–32 7
Table 2.3.1. Cytotoxicity of Compounds 35, 37, 38, 40, 44 and 45 11
Table 2.3.2. Cytotoxicity of 39, 40, 43, 44 and 46–48 12
Table 2.3.3. Cytotoxicity of 35, 37, 40, 44, 45 and 50 13
Table 2.3.4. Cytotoxicity of 39 and an Epimer Mixture 39/40 14
Table 2.3.5. Cytotoxicity of 53–58, 60, 63 and 64 18
Table 2.4.1. Reversal of Multidrug Resistance 21
Table 2.4.2. IC50 Values for Cytotoxicity Against NBT-T2 Cells 23
Table 2.5. Cytotoxic Data of Sesquiterpenes 84–89 25
Table 4.1.1. Spectroscopic and Physical Data of 1 39
Table 4.1.2. 13C Chemical Shifts (CDCl3) for 1, 14–16, 21 and 27–29 41
Table 4.2.1. Spectroscopic and Physical Data of 2 56
Table 4.2.2. 13C Chemical Shifts (CDCl3) for 2, 1, 20, 22, 23, 33 and 34 58
Table 4.3.1. Spectroscopic and Physical Data of 3 73
Table 4.3.2. 13C Chemical shifts (CDCl3) for 3, 20, 21, 24 and 25 75
Table 4.4.1. Spectroscopic and Physical Data of 4 90
Table 4.4.2. 13C and 1H Chemical Shifts (CDCl3) for 4 and 21 92
Table 4.5.1. Spectroscopic and Physical Data of 5 106
Table 4.5.2. 13C Chemical Shifts for 5 and 93–94 108
Table 4.6. Spectroscopic and Physical Data of 6 124
Table 4.7.1. Spectroscopic and Physical Data of 7 140
Table 4.7.2. 13C Chemical Shifts (CDCl3) for 22R Spiro Ketal Steroids 143
Table 4.7.3. 13C Chemical Shifts (CDCl3) for 22S Spiro Ketal Steroids 143
Table 4.8.1. Spectroscopic and Physical Data of 8 159
Table 4.8.2. 13C Chemical Shifts (CDCl3) for 8, 12, 13, 66, 71, 73 and 77 161
Table 4.9.1. Spectroscopic and Physical Data of 9 175
Table 4.9.2. 13C Chemical Shifts (CDCl3) for 9 and 30 177
Table 4.10. Spectroscopic and Physical Data of 10 194
Table 4.11. Spectroscopic and Physical Data of 11 210
Table 4.12. Spectroscopic and Physical Data of 12 226
Table 4.13. Spectroscopic and Physical Data of 13 241
Table 5.1. Cytotoxicity of Metabolites 1–13 251
Table 5.2. Anti-HCMV of Compounds 1–13 253

圖 目 錄
Figure 2.1. X-ray crystal structure of 14 4
Figure 2.3.1. X-ray crystal structure of 36 8
Figure 2.3.2. X-ray crystal structure of 49 12
Figure 2.3.3. X-ray crystal structure of 55 15
Figure 2.3.4. X-ray crystal structure of 53 17
Figure 2.3.5. X-ray crystal structure of 54 17
Figure 2.4. X-ray crystal structure of 66 21
Figure 3.3. Isis hippuris 29
Figure 3.4.1. Extraction and Isolation 33
Figure 3.4.2. HPLC chromatogram of LY19-28-2-2 34
Figure 3.4.3. HPLC chromatogram of LY19-28-3-2 34
Figure 3.4.4. HPLC chromatogram of LY19-28-3-3 35
Figure 3.4.5. HPLC chromatogram of LY19-29-3-2-2 35
Figure 4.1.1. IR spectrum of 1 38
Figure 4.1.2. ESIMS spectrum of 1 40
Figure 4.1.3. HRESIMS spectrum of 1 40
Figure 4.1.4. 1H NMR spectrum of 1 42
Figure 4.1.5. Expansion of upfield 1H NMR spectrum of 1 43
Figure 4.1.6. 13C NMR spectrum of 1 44
Figure 4.1.7. 13C NMR and DEPT spectra of 1 45
Figure 4.1.8. HSQC spectrum of 1 46
Figure 4.1.9. Partial expansion of upfield HSQC spectrum of 1 47
Figure 4.1.10. COSY spectrum of 1 48
Figure 4.1.11. Partial expansion of upfield COSY spectrum of 1 49
Figure 4.1.12. HMBC spectrum of 1 50
Figure 4.1.13. Partial expansion of upfield HMBC spectrum of 1 51
Figure 4.1.14. NOESY spectrum of 1 52
Figure 4.1.15. Partial expansion of upfield NOESY spectrum of 1 53
Figure 4.2.1. IR spectrum of 2 55
Figure 4.2.2. ESIMS spectrum of 2 57
Figure 4.2.3. HRESIMS spectrum of 2 57
Figure 4.2.4. 1H NMR spectrum of 2 59
Figure 4.2.5. Expansion of upfield 1H NMR spectrum of 2 60
Figure 4.2.6. 13C NMR spectrum of 2 61
Figure 4.2.7. 13C NMR and DEPT spectra of 2 62
Figure 4.2.8. HSQC spectrum of 2 63
Figure 4.2.9. Partial expansion of upfield HSQC spectrum of 2 64
Figure 4.2.10. COSY spectrum of 2 65
Figure 4.2.11. HMBC spectrum of 2 66
Figure 4.2.12. Partial expansion of upfield HMBC spectrum of 2 67
Figure 4.2.13. NOESY spectrum of 2 68
Figure 4.2.14. Partial expansion of upfield NOESY spectrum of 2 69
Figure 4.3.1. IR spectrum of 3 72
Figure 4.3.2. ESIMS spectrum of 3 74
Figure 4.3.3. HRESIMS spectrum of 3 74
Figure 4.3.4. 1H NMR spectrum of 3 76
Figure 4.3.5. Expansion of upfield 1H NMR spectrum of 3 77
Figure 4.3.6. 13C NMR spectrum of 3 78
Figure 4.3.7. 13C NMR and DEPT spectra of 3 79
Figure 4.3.8. HSQC spectrum of 3 80
Figure 4.3.9. Partial expansion of upfield HSQC spectrum of 3 81
Figure 4.3.10. COSY spectrum of 3 82
Figure 4.3.11. Partial expansion of upfield COSY spectrum of 3 83
Figure 4.3.12. HMBC spectrum of 3 84
Figure 4.3.13. Partial expansion of upfield HMBC spectrum of 3 85
Figure 4.3.14. NOESY spectrum of 3 86
Figure 4.3.15. Partial expansion of upfield NOESY spectrum of 3 87
Figure 4.4.1. IR spectrum of 4 89
Figure 4.4.2. ESIMS spectrum of 4 91
Figure 4.4.3. HRESIMS spectrum of 4 91
Figure 4.4.4. 1H NMR spectrum of 4 93
Figure 4.4.5. Expansion of upfield 1H NMR spectrum of 4 94
Figure 4.4.6. 13C NMR spectrum of 4 95
Figure 4.4.7. 13C NMR and DEPT spectra of 4 96
Figure 4.4.8. HSQC spectrum of 4 97
Figure 4.4.9. Partial expansion of upfield HSQC spectrum of 4 98
Figure 4.4.10. COSY spectrum of 4 99
Figure 4.4.11. Partial expansion of upfield COSY spectrum of 4 100
Figure 4.4.12. HMBC spectrum of 4 101
Figure 4.4.13. Partial expansion of upfield HMBC spectrum of 4 102
Figure 4.4.14. NOESY spectrum of 4 103
Figure 4.4.15. Partial expansion of upfield NOESY spectrum of 4 104
Figure 4.5.1. ESIMS spectrum of 5 107
Figure 4.5.2. HRESIMS spectrum of 5 107
Figure 4.5.3. IR spectrum of 5 108
Figure 4.5.4. 1H NMR spectrum of 5 109
Figure 4.5.5. Expansion of upfield 1H NMR spectrum of 5 110
Figure 4.5.6. 13C NMR spectrum of 5 111
Figure 4.5.7. 13C NMR and DEPT spectra of 5 112
Figure 4.5.8. HSQC spectrum of 5 113
Figure 4.5.9. Partial expansion of upfield HSQC spectrum of 5 114
Figure 4.5.10. COSY spectrum of 5 115
Figure 4.5.11. Partial expansion of upfield COSY spectrum of 5 116
Figure 4.5.12. HMBC spectrum of 5 117
Figure 4.5.13. Partial expansion of upfield HMBC spectrum of 5 118
Figure 4.5.14. NOESY spectrum of 5 119
Figure 4.5.15. Partial expansion of upfield NOESY spectrum of 5 120
Figure 4.6.1. IR spectrum of 6 123
Figure 4.6.2. ESIMS spectrum of 6 125
Figure 4.6.3. HRESIMS spectrum of 6 125
Figure 4.6.4. 1H NMR spectrum of 6 126
Figure 4.6.5. Expansion of upfield 1H NMR spectrum of 6 127
Figure 4.6.6. 13C NMR spectrum of 6 128
Figure 4.6.7. 13C NMR and DEPT spectra of 6 129
Figure 4.6.8. HSQC spectrum of 6 130
Figure 4.6.9. Partial expansion of upfield HSQC spectrum of 6 131
Figure 4.6.10. COSY spectrum of 6 132
Figure 4.6.11. Partial expansion of upfield COSY spectrum of 6 133
Figure 4.6.12. HMBC spectrum of 6 134
Figure 4.6.13. Partial expansion of upfield HMBC spectrum of 6 135
Figure 4.6.14. NOESY spectrum of 6 136
Figure 4.6.15. Partial expansion of upfield NOESY spectrum of 6 137
Figure 4.7.1. ESIMS spectrum of 7 141
Figure 4.7.2. HRESIMS spectrum of 7 141
Figure 4.7.3. IR spectrum of 7 142
Figure 4.7.4. Key NOE correlations for Compounds 6 and 7 142
Figure 4.7.4. 1H NMR spectrum of 7 144
Figure 4.7.5. Expansion of upfield 1H NMR spectrum of 7 145
Figure 4.7.6. 13C NMR spectrum of 7 146
Figure 4.7.7. 13C NMR and DEPT spectra of 7 147
Figure 4.7.8. HSQC spectrum of 7 148
Figure 4.7.9. Partial expansion of upfield HSQC spectrum of 7 149
Figure 4.7.10. COSY spectrum of 7 150
Figure 4.7.11. Partial expansion of upfield COSY spectrum of 7 151
Figure 4.7.12. HMBC spectrum of 7 152
Figure 4.7.13. Partial expansion of upfield HMBC spectrum of 7 153
Figure 4.7.14. NOESY spectrum of 7 154
Figure 4.7.15. Partial expansion of upfield NOESY spectrum of 7 155
Figure 4.8.1. IR spectrum of 8 158
Figure 4.8.2. ESIMS spectrum of 8 160
Figure 4.8.3. HRESIMS spectrum of 8 160
Figure 4.8.4. 1H NMR spectrum of 8 162
Figure 4.8.5. Expansion of upfield 1H NMR spectrum of 8 163
Figure 4.8.6. 13C NMR spectrum of 8 164
Figure 4.8.7. 13C NMR and DEPT spectra of 8 165
Figure 4.8.8. HSQC spectrum of 8 166
Figure 4.8.9. Partial expansion of upfield HSQC spectrum of 8 167
Figure 4.8.10. COSY spectrum of 8 168
Figure 4.8.11. HMBC spectrum of 8 169
Figure 4.8.12. Partial expansion of upfield HMBC spectrum of 8 170
Figure 4.8.13. NOESY spectrum of 8 171
Figure 4.8.14. Partial expansion of upfield NOESY spectrum of 8 172
Figure 4.9.1. IR spectrum of 9 174
Figure 4.9.2. ESIMS spectrum of 9 176
Figure 4.9.3. HRESIMS spectrum of 9 176
Figure 4.9.4. 1H NMR spectrum of 9 178
Figure 4.9.5. Expansion of 1H NMR spectrum of 9 179
Figure 4.9.6. Expansion of 1H NMR spectrum of 9 180
Figure 4.9.7. 13C NMR spectrum of 9 181
Figure 4.9.8. 13C NMR and DEPT spectra of 9 182
Figure 4.9.9. HSQC spectrum of 9 183
Figure 4.9.10. Partial expansion of upfield HSQC spectrum of 9 184
Figure 4.9.11. COSY spectrum of 9 185
Figure 4.9.12. Partial expansion of upfield COSY spectrum of 9 186
Figure 4.9.13. HMBC spectrum of 9 187
Figure 4.9.14. Partial expansion of upfield HMBC spectrum of 9 188
Figure 4.9.15. NOESY spectrum of 9 189
Figure 4.9.16. Partial expansion of upfield NOESY spectrum of 9 190
Figure 4.10.1. IR spectrum of 10 193
Figure 4.10.2. ESIMS spectrum of 10 195
Figure 4.10.3. HRESIMS spectrum of 10 195
Figure 4.10.4. 1H NMR spectrum of 10 196
Figure 4.10.5. Expansion of upfield 1H NMR spectrum of 10 197
Figure 4.10.6. 13C NMR and DEPT spectra of 10 198
Figure 4.10.7. Expansion of 13C NMR and DEPT spectra of 10 199
Figure 4.10.8. HSQC spectrum of 10 200
Figure 4.10.9. Partial expansion of upfield HSQC spectrum of 10 201
Figure 4.10.10. COSY spectrum of 10 202
Figure 4.10.11. Partial expansion of upfield COSY spectrum of 10 203
Figure 4.10.12. HMBC spectrum of 10 204
Figure 4.10.13. Partial expansion of upfield HMBC spectrum of 10 205
Figure 4.10.14. NOESY spectrum of 10 206
Figure 4.10.15. Partial expansion of upfield NOESY spectrum of 10 207
Figure 4.11.1. IR spectrum of 11 209
Figure 4.11.2. ESIMS spectrum of 11 211
Figure 4.11.3. HRESIMS spectrum of 11 211
Figure 4.11.4. 1H NMR spectrum of 11 212
Figure 4.11.5. Expansion of upfield 1H NMR spectrum of 11 213
Figure 4.11.6. 13C NMR spectrum of 11 214
Figure 4.11.7. 13C NMR and DEPT spectra of 11 215
Figure 4.11.8. HSQC spectrum of 11 216
Figure 4.11.9. Partial expansion of upfield HSQC spectrum of 11 217
Figure 4.11.10. COSY spectrum of 11 218
Figure 4.11.11. Partial expansion of upfield COSY spectrum of 11 219
Figure 4.11.12. HMBC spectrum of 11 220
Figure 4.11.13. Partial expansion of upfield HMBC spectrum of 11 221
Figure 4.11.14. NOESY spectrum of 11 222
Figure 4.11.15. Partial expansion of upfield NOESY spectrum of 11 223
Figure 4.12.1. IR spectrum of 12 225
Figure 4.12.2. ESIMS spectrum of 12 227
Figure 4.12.3. HRESIMS spectrum of 12 227
Figure 4.12.4. 1H NMR spectrum of 12 228
Figure 4.12.5. Expansion of upfield 1H NMR spectrum of 12 229
Figure 4.12.6. 13C NMR and DEPT spectra of 12 230
Figure 4.12.7. HSQC spectrum of 12 231
Figure 4.12.8. Partial expansion of upfield HSQC spectrum of 12 232
Figure 4.12.9. COSY spectrum of 12 233
Figure 4.12.10. Partial expansion of upfield COSY spectrum of 12 234
Figure 4.12.11. HMBC spectrum of 12 235
Figure 4.12.12. Partial expansion of upfield HMBC spectrum of 12 236
Figure 4.12.13. NOESY spectrum of 12 237
Figure 4.12.14. Partial expansion of upfield NOESY spectrum of 12 238
Figure 4.13.1. IR spectrum of 13 240
Figure 4.13.2. ESIMS spectrum of 13 242
Figure 4.13.3. HRESIMS spectrum of 13 242
Figure 4.13.4. 1H NMR spectrum of 13 243
Figure 4.13.5. Expansion of upfield 1H NMR spectrum of 13 244
Figure 4.13.6. 13C NMR spectrum of 13 245
Figure 4.13.7. 13C NMR and DEPT spectra of 13 246
Figure 4.13.8. HSQC spectrum of 13 247
Figure 4.13.9. Partial expansion of upfield HSQC spectrum of 13 248
Figure 6.1. Possible biogenetic pathway for 10 255
Figure 6.2. Possible biogenetic pathway for 11 255

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