為了從台灣海域中的軟珊瑚和柳珊瑚開發新的藥物，我們針對三種軟珊瑚Nephthea chabrolii、Sinularia manaarensis、Sinularia leptoclados和一種柳珊瑚Briareum sp.的有機萃取物來找尋活性物質。從上述四種珊瑚的研究分析中共得到五十五個化合物(1–55)，其中從軟珊瑚N. chabrolii中分離出24個新天然化合物1–7、9–18、20–24、26和27和3個已知的化合物8、19和25。在這些新天然物中化合物1–7和9–18屬於meroditerpenoids、化合物20和21為18個碳的terpenoids、化合物22–24為sesquiterpenoids及化合物26和27為steroids。從軟珊瑚S. manaarensis樣品中分離出11個cembrane類的天然化合物，其中有9個新天然化合物28–36與2個已知的天然化合物37和38。從軟珊瑚S. leptoclados中分離出5個新的sesquiterpenoids的天然化合物39–43和1新個steroid47與3個已知的天然化合物44–46；最後從柳珊瑚Briareum sp.樣品中分離出8個briarane類的天然化合物，其中有3個新天然化合物48–50與5個已知的天然化合物51–55。化合物1–55的結構均是經由光譜資料分析和比對相關文獻化合物而建立。而化合物39的結構是經由X-ray單晶繞射解析更加確定其立體位向。此外，meroditerpenoids1、4、11和20的生合成路徑也在本論文中被提出，並且化合物1–3為一個甲基和hydroxybenzoquinone片段合環成一個naphthoquinone片段的新骨架化合物。
上述化合物在細胞毒殺活性測試結果顯示，化合物2和10在濃度為20μg/mL對三種癌細胞MCF 7、NCI-H460和SF-268具有良好的細胞毒殺活性，並且化合物2對MDA-MB-231癌細胞也顯示出良好的毒殺活性，也對Hep G2和A-549兩種癌細胞也有較小的細胞毒殺活性，而化合物10對這三種癌細胞(MDA–MB–231、Hep G2和A-549)均有微弱的細胞毒殺。此外，化合物34和35對另外四種癌細胞Hepa59T/VGH、KB、Hela和Med也有中等的細胞毒殺活性。

In order to discover and develop new drug from soft corals and gorgonian corals of Taiwan, we have searched the bioactive metabolites from the organic extracts of three soft corals Nephthea chabrolii, Sinularia manaarensis, Sinularia leptoclados, and one Gorgonian of Briareum genus. This study had led to the isolation of fifty-five natural products (1–55), including seventeen new meroditerpenoid-related metabolites (1–7 and 9–18), two new C18 terpenoid–related carboxylic acids (20 and 21), three new sesquiterpenoidalnatural products (22–24), and two new steroids (26 and 27), along with three known compounds (8, 19, and 25) from N. chabrolii; nine new cembrane-type
diterpenoids (28–36), along with two known cembranolides 37 and 38 from S.manaarensis; five new sesquiterpenoids (39–43), one steroid (47) isolated for the first time from natural sources and three known metabolites (44–46) from S.
leptoclados; and three new briarane-type derivatives (48–50) and five known briarane-type compounds (51–55) from Briareum sp. The structures of metabolites 1–55, including their stereochemistries have been established by detailed spectroscopic analyses, particularly mass, 2D NMR (1H–1H COSY, HMQC, HMBC, and NOESY) spectroscopy and by comparison with the related physical and spectral data form other known compounds. The relative configuration of metabolite 39 was further confirmed by X-ray single-crystal analysis. Furthermore, the biosyntheses of meroditerpenoids 1, 4, 11, and 20 were proposed. To the best of our knowledge, the incorporation of a methyl group of the related meroditerpene to form a naphthoquinone as discovered herein for the first time.

In above metabolites, two compounds (2 and 10) were found to exhibit significant inhibition against the growth of MCF 7, NCI-H460, and SF-268 tumor cells at 20 μg/mL. Also, compound 2 exhibited significant cytotoxicity against the growth of MDA–MB–231cancer cell line, and moderate to weak
cytotoxicity against Hep G2 and A-549 cancer cell lines and metabolite 10 exhibited moderate to weak cytotoxicity toward MDA–MB–231, Hep G2 and A-549 cancer cell lines. Furthermore, Two cembranolides (34 and 35) exhibited moderate cytotoxicity against Hepa59T/VGH, KB, Hela, and Med cell lines.

中文摘要 1
英文摘要 2
化合物1–55的結構 4
第一章、緒論
第一節、研究之動機及目的 7
第二節、台灣海域八放珊瑚所含化學成分的文獻回顧 12
第三節、穗珊瑚Nephthea屬化學成分過去相關研究 68
第四節、指形軟珊瑚Sinularia屬所含cembrane類的化學成分過去相關研究 76
第五節、柳珊瑚Briareum屬所含briarane類的化學成分過去相關研究 84
第二章、實驗程序與方法
第一節、實驗程序 98
第二節、Nephthea chabrolii樣品採集時間、地點、分類地位及分離流程 99
第三節、Sinularia manaarensis樣品採集時間、地點、分類地位及分離流程 101
第四節、Sinularia leptoclados樣品採集時間、地點、分類地位及分離流程 103
第五節、Briareum sp.樣品採集時間、地點、分類地位及分離流程 105
第六節、實驗設備儀器及材料 107
第三章、化合物之結構證明
第一節、軟珊瑚Nephthea chabrolii所分離出之化合物的結構證明 109
(一)、chabrolonaphthoquinone A (1) 111
(二)、chabrolonaphthoquinone B (2) 118
(三)、chabrolonaphthoquinone C (3) 126 (四)、chabrolohydroxybenzoquinone A (4) 132
(五)、chabrolohydroxybenzoquinone B (5) 138 (六)、chabrolohydroxybenzoquinone C (6) 144
(七)、chabrolohydroxybenzoquinone D (7) 150
(八)、2,7-dimethyl-2-[(E,E)-4’,8’,12’-trimethyltrideca-3’,7’,11’-trienyl]-2H-
1-benzopyran-6-ol (8) 156
(九)、chabrolohydroxybenzoquinone F (9) 162
(十)、chabrolohydroxybenzoquinone G (10) 168
(十一)、chabrolobenzoquinone A (11) 174
(十二)、chabrolobenzoquinone B (12) 180
(十三)、chabrolobenzoquinone C (13) 186
(十四)、chabrolobenzoquinone D (14) 192
(十五)、chabrolobenzoquinone E (15) 198
(十六)、chabrolobenzoquinone F (16) 204
(十七)、chabrolobenzoquinone G (17) 210
(十八)、chabrolobenzoquinone H (18) 216
(十九)、5-methyl-2-tetraprenyl-p-benzoquinone (19) 222
(二十)、ketochabrolic acid (20) 224
(二十一)、isoketochabrolic acid (21) 230
(二十二)、chabrolene (22) 236
(二十三)、chabrolidione A (23) 243
(二十四)、chabrolidione B (24) 250
(二十五)、(+)-aristolone (25) 256
(二十六)、chabrolosteroid H (26) 258
(二十七)、chabrolosteroid I (27) 265
第二節、軟珊瑚Sinularia manaarensis所分離出之化合物的結構證明 273
(二十八)、manaarenolide A (28) 274
(二十九)、manaarenolide B (29) 282
(三十)、manaarenolide C (30) 289
(三十一)、manaarenolide D (31) 295
(三十二)、manaarenolide E (32) 301
(三十三)、manaarenolide F (33) 308
(三十四)、manaarenolide G (34) 316
(三十五)、manaarenolide H (35) 323
(三十六)、manaarenolide I (36) 330
(三十七)、sinularin (37) 336
(三十八)、dihydrosinularin (38) 336
第三節、軟珊瑚Sinularia leptoclados所分離出之化合物的結構證明 339
(三十九)、letocladol A (39) 340
(四十)、letocladol B (40) 348
(四十一)、letocladol C (41) 355
(四十二)、letocladol D (42) 362
(四十三)、1-epi-chabrolidione A (43) 369
(四十四)、lβ,6α-dihydroxyeudesm-4(15)-ene (44) 375
(四十五)、4β,10α-aromadendranediol (45) 377
(四十六)、(-)-β-elemene (46) 379
(四十七)、3β,11-dihydroxy-24-methylene-9,11-secocholestan-9-one (47) 381
第四節、柳珊瑚Briareum sp.所分離出之化合物的結構證明 389
(四十八)、briarenolide A (48) 390
(四十九)、briarenolide B (49) 398
(五十)、briarenolide C (50) 406
(五十一)、(1R*,2R*,5Z,7R*,8S*,9R*,10R*,12R*,14R*,17S*)-2,14-diacetoxy-
8,17-epoxy- 9,12-dihydroxybriara-5,11(20)-dien-19-one (51) 414
(五十二)、2β-acetoxy-2-(debutyryloxy)stecholide E Acetate (52) 416
(五十三)、briaexcavatolide T (53) 418
(五十四)、stecholide C Acetate (54) 420
(五十五)、milolide B (55) 422
第四章、細胞毒殺活性試驗
第一節：細胞毒殺活性檢測方法 424
第二節：細胞毒殺活性檢測結果 425
第五章、結論 429
第六章、化合物之物理及圖譜資料 432
第七章、參考資料 440
附錄一、化合物39之X-ray實驗數據 458
附錄二、個人資料暨研究成果目錄 465


圖目錄
頁次
Figure 3-1-1. Key 1H-1H COSY and HMBC correlations for 1 112
Figure 3-1-2. Selective 1H and 13C data measured in CDCl3 for 67-69 112
Figure 3-1-3. EIMS spectrum of 1 114
Figure 3-1-4. HREIMS spectrum of 1 114
Figure 3-1-5. 1H NMR spectrum of 1 115
Figure 3-1-6. 13C NMR and DEPT spectra of 1 115
Figure 3-1-7. COSY spectrum of 1 116
Figure 3-1-8. HMQC spectrum of 1 116
Figure 3-1-9. HMBC spectrum of 1 117
Figure 3-2-1. Key 1H-1H COSY and HMBC correlations for 2 119
Figure 3-2-2. Selective NOE correlations of 2 119
Figure 3-2-3. Carbons shifts of C-9 and C-15 of 1 relative to those of C-5 and C-14 of squalene derivatives 70 and 71 119
Figure 3-2-4. Optical rotations of 2 and 72 119
Figure 3-2-5. EIMS spectrum of 2 122
Figure 3-2-6. HREIMS spectrum of 2 122
Figure 3-2-7. 1H NMR spectrum of 2 123
Figure 3-2-8. 13C NMR and DEPT spectra of 2 123
Figure 3-2-9. COSY spectrum of 2 124
Figure 3-2-10. HMQC spectrum of 2 124
Figure 3-2-11. HMBC spectrum of 2 125
Figure 3-2-11. NOESY spectrum of 2 125
Figure 3-3-1. Key 1H-1H COSY and HMBC correlations for 3 126
Figure 3-3-2. ESIMS spectrum of 3 128
Figure 3-3-3. HRESIMS spectrum of 3 128
Figure 3-3-4. 1H NMR spectrum of 3 129
Figure 3-3-5. 13C NMR spectrum of 3 129
Figure 3-3-6. COSY spectrum of 3 130
Figure 3-3-7. HMQC spectrum of 3 130
Figure 3-3-8. HMBC spectrum of 3 131
Figure 3-4-1. Key 1H-1H COSY and HMBC correlations for 4 133
Figure 3-4-2. EIMS spectrum of 4 134
Figure 3-4-3. HREIMS spectrum of 4 134
Figure 3-4-4. 1H NMR spectrum of 4 135
Figure 3-4-5. 13C NMR spectrum of 4 135
Figure 3-4-6. COSY spectrum of 4 136
Figure 3-4-7. HMQC spectrum of 4 136
Figure 3-4-8. HMBC spectrum of 4 137
Figure 3-4-9. DEPT spectrum of 4 137
Figure 3-5-1. Key 1H-1H COSY and HMBC correlations for 5 138
Figure 3-5-2. EIMS spectrum of 5 140
Figure 3-5-3. HREIMS spectrum of 5 140
Figure 3-5-4. 1H NMR spectrum of 5 141
Figure 3-5-5. 13C NMR and DEPT spectra of 5 141
Figure 3-5-6. COSY spectrum of 5 142
Figure 3-5-7. HMQC spectrum of 5 142
Figure 3-5-8. HMBC spectrum of 5 143
Figure 3-6-1. Key 1H-1H COSY and HMBC correlations for 6 144
Figure 3-6-2. EIMS spectrum of 6 146
Figure 3-6-3. HREIMS spectrum of 6 146
Figure 3-6-4. 1H NMR spectrum of 6 147
Figure 3-6-5. 13C NMR and DEPT spectra of 6 147
Figure 3-6-6. COSY spectrum of 6 148
Figure 3-6-7. HMQC spectrum of 6 148
Figure 3-6-8. HMBC spectrum of 6 149
Figure 3-7-1. Key 1H-1H COSY and HMBC correlations for 7 150
Figure 3-7-2. EIMS spectrum of 7 152
Figure 3-7-3. HREIMS spectrum of 7 152
Figure 3-7-4. 1H NMR spectrum of 7 153
Figure 3-7-5. 13C NMR and DEPT spectra of 7 153
Figure 3-7-6. COSY spectrum of 7 154
Figure 3-7-7. HMQC spectrum of 7 154
Figure 3-7-8. HMBC spectrum of 7 155
Figure 3-8-1. Key 1H-1H COSY and HMBC correlations for 8 156
Figure 3-8-2. ESIMS spectrum of 8 158
Figure 3-8-3. HRESIMS spectrum of 8 158
Figure 3-8-4. 1H NMR spectrum of 8 159
Figure 3-8-5. 13C NMR and DEPT spectra of 8 159
Figure 3-8-6. COSY spectrum of 8 160
Figure 3-8-7. HMQC spectrum of 8 160
Figure 3-8-8. HMBC spectrum of 8 161
Figure 3-9-1. Key 1H-1H COSY and HMBC correlations for 9 162
Figure 3-9-2. EIMS spectrum of 9 164
Figure 3-9-3. HRESIMS spectrum of 9 164
Figure 3-9-4. 1H NMR spectrum of 9 165
Figure 3-9-5. 13C NMR and DEPT spectra of 9 165
Figure 3-9-6. COSY spectrum of 9 166
Figure 3-9-7. HMQC spectrum of 9 166
Figure 3-9-8. HMBC spectrum of 9 167
Figure 3-10-1. Key 1H-1H COSY and HMBC correlations for 10 168
Figure 3-10-2. EIMS spectrum of 10 170
Figure 3-10-3. HREIMS spectrum of 10 170
Figure 3-10-4. 1H NMR spectrum of 10 171
Figure 3-10-5. 13C NMR and DEPT spectra of 10 171
Figure 3-10-6. COSY spectrum of 10 172
Figure 3-10-7. HMQC spectrum of 10 172
Figure 3-10-8. HMBC spectrum of 10 173
Figure 3-11-1. Key 1H-1H COSY and HMBC correlations for 11 175
Figure 3-11-2. EIMS spectrum of 11 176
Figure 3-11-3. HREIMS spectrum of 11 176
Figure 3-11-4. 1H NMR spectrum of 11 177
Figure 3-11-5. 13C NMR and DEPT spectra of 11 177
Figure 3-11-6. COSY spectrum of 11 178
Figure 3-11-7. HMQC spectrum of 11 178
Figure 3-11-8. HMBC spectrum of 11 179
Figure 3-12-1. EIMS spectrum of 12 182
Figure 3-12-2. HREIMS spectrum of 12 182
Figure 3-12-3. 1H NMR spectrum of 12 183
Figure 3-12-4. 13C NMR spectrum of of 12 183
Figure 3-12-5. COSY spectrum of 12 184
Figure 3-12-6. HMQC spectrum of 12 184
Figure 3-12-7. HMBC spectrum of 12 185
Figure 3-13-1. EIMS spectrum of 13 188
Figure 3-13-2. HREIMS spectrum of 13 188
Figure 3-13-3. 1H NMR spectrum of 13 189
Figure 3-13-4. 13C NMR spectrum of 13 189
Figure 3-13-5. COSY spectrum of 13 190
Figure 3-13-6. HMQC spectrum of 13 190
Figure 3-13-7. HMBC spectrum of 13 191
Figure 3-14-1. EIMS spectrum of 14 194
Figure 3-14-2. HREIMS spectrum of 14 194
Figure 3-14-3. 1H NMR spectrum of 14 195
Figure 3-14-4. 13C NMR spectrum of 14 195
Figure 3-14-5. COSY spectrum of 14 196
Figure 3-14-6. HMQC spectrum of 14 196
Figure 3-14-7. HMBC spectrum of 14 197
Figure 3-15-1. Key 1H-1H COSY and HMBC correlations for 15 198
Figure 3-15-2. EIMS spectrum of 15 200
Figure 3-15-3. HRESIMS spectrum of 15 200
Figure 3-15-4. 1H NMR spectrum of 15 201
Figure 3-15-5. 13C NMR spectrum of 15 201
Figure 3-15-6. COSY spectrum of 15 202
Figure 3-15-7. HMQC spectrum of 15 202
Figure 3-15-8. HMBC spectrum of 15 203
Figure 3-15-9. NOESY spectrum of 15 203
Figure 3-16-1. ESIMS spectrum of 16 206
Figure 3-16-2. HRESIMS spectrum of 16 206
Figure 3-16-3. 1H NMR spectrum of 16 207
Figure 3-16-4. 13C NMR spectrum of 16 207
Figure 3-16-5. COSY spectrum of 16 208
Figure 3-16-6. HMQC spectrum of 16 208
Figure 3-16-7. HMBC spectrum of 16 209
Figure 3-17-1. Key 1H-1H COSY and HMBC correlations for 17 210
Figure 3-17-2. EIMS spectrum of 17 212
Figure 3-17-3. HREIMS spectrum of 17 212
Figure 3-17-4. 1H NMR spectrum of 17 213
Figure 3-17-5. 13C NMR spectrum of 17 213
Figure 3-17-6. COSY spectrum of 17 214
Figure 3-17-7. HMQC spectrum of 17 214
Figure 3-17-8. HMBC spectrum of 17 215
Figure 3-17-9. DEPT spectrum of 17 215
Figure 3-18-1. EIMS spectrum of 18 218
Figure 3-18-2. HREIMS spectrum of 18 218
Figure 3-18-3. 1H NMR spectrum of 18 219
Figure 3-18-4. 13C NMR spectrum of 18 219
Figure 3-18-5. COSY spectrum of 18 220
Figure 3-18-6. HMQC spectrum of 18 220
Figure 3-18-7. HMBC spectrum of 18 221
Figure 3-19-1. 1H NMR spectrum of 19 222
Figure 3-19-2. 13C NMR spectrum of 19 223
Figure 3-20-1. Key 1H-1H COSY and HMBC correlations for 20 224
Figure 3-20-2. ESIMS spectrum of 20 226
Figure 3-20-3. HRESIMS spectrum of 20 226
Figure 3-20-4. 1H NMR spectrum of 20 227
Figure 3-20-5. 13C NMR and DEPT spectra of 20 227
Figure 3-20-6. COSY spectrum of 20 228
Figure 3-20-7. HMQC spectrum of 20 228
Figure 3-20-8. HMBC spectrum of 20 229
Figure 3-21-1. ESIMS spectrum of 21 232
Figure 3-21-2. HRESIMS spectrum of 21 232
Figure 3-21-3. 1H NMR spectrum of 21 233
Figure 3-21-4. 13C NMR and DEPT spectra of 21 233
Figure 3-21-5. COSY spectrum of 21 234
Figure 3-21-6. HMQC spectrum of 21 234
Figure 3-21-7. HMBC spectrum of 21 235
Figure 3-22-1. Key 1H-1H COSY, HMBC,and NOESY correlations for 22 237
Figure 3-22-2. EIMS spectrum of 22 238
Figure 3-22-3. HREIMS spectrum of 22 238
Figure 3-22-4. 1H NMR spectrum of 22 239
Figure 3-22-5. 13C NMR and DEPT spectra of 22 240
Figure 3-22-6. COSY spectrum of 22 241
Figure 3-22-7. HMQC spectrum of 22 241
Figure 3-22-8. HMBC spectrum of 22 242
Figure 3-22-9. NOESY spectrum of 22 242
Figure 3-23-1. Key 1H-1H COSY, HMBC and NOESY correlations for 23 244
Figure 3-23-2. EIMS spectrum of 23 245
Figure 3-23-3. HREIMS spectrum of 23 245
Figure 3-23-4. 1H NMR spectrum of 23 246
Figure 3-23-5. 13C NMR and DEPT spectra of 23 247
Figure 3-23-6. COSY spectrum of 23 247
Figure 3-23-7. HMQC spectrum of 23 248
Figure 3-23-8. HMBC spectrum of 23 248
Figure 3-23-9. NOESY spectrum of 23 249
Figure 3-24-1. Key 1H-1H COSY and HMBC correlations for 24 251
Figure 3-24-2. ESIMS spectrum of 24 252
Figure 3-24-3. HRESIMS spectrum of 24 252
Figure 3-24-4. 1H NMR spectrum of 24 253
Figure 3-24-5. 13C NMR and DEPT spectra of 24 253
Figure 3-24-6. COSY spectrum of 24 254
Figure 3-24-7. HMQC spectrum of 24 254
Figure 3-24-8. HMBC spectrum of 24 255
Figure 3-25-1. EIMS spectrum of 25 256
Figure 3-25-2. 1H NMR spectrum of 25 257
Figure 3-25-3. 13C NMR and DEPT spectra of 25 257
Figure 3-26-1. Key 1H-1H COSY, HMBC, nd NOESY correlations for 26 259
Figure 3-26-2. ESIMS spectrum of 26 261
Figure 3-26-3. HRESIMS spectrum of 26 261
Figure 3-26-4. 1H NMR spectrum of 26 262
Figure 3-26-5. 13C NMR and DEPT spectra of 26 262
Figure 3-26-6. COSY spectrum of 26 263
Figure 3-26-7. HMQC spectrum of 26 263
Figure 3-26-8. HMBC spectrum of 26 264
Figure 3-26-9. NOESY spectrum of 26 264
Figure 3-27-1. Key 1H-1H COSY and HMBC correlations for 27 266
Figure 3-27-2. Key NOESY correlations for 27 266
Figure 3-27-3. ESIMS spectrum of 27 268
Figure 3-27-4. HRESIMS spectrum of 27 268
Figure 3-27-5. 1H NMR spectrum of 27 269
Figure 3-27-6. 13C NMR and DEPT spectra of 27 270
Figure 3-27-7. COSY spectrum of 27 270
Figure 3-27-8. HMQC spectrum of 27 271
Figure 3-27-9. HMBC spectrum of 27 271
Figure 3-27-10. NOESY spectrum of 27 272
Figure 3-28-1. 1H-1H COSY and HMBC correlations for 28 275
Figure 3-28-2. Key NOESY correlations for 28 276
Figure 3-28-3. ESIMS spectrum of 28 277
Figure 3-28-4. HRESIMS spectrum of 28 277
Figure 3-28-5. 1H NMR spectrum of 28 278
Figure 3-28-6. 13C NMR and DEPT spectra of 28 279
Figure 3-28-7. COSY spectrum of 28 280
Figure 3-28-8. HMQC spectrum of 28 280
Figure 3-28-9. HMBC spectrum of 28 281
Figure 3-28-10. NOESY spectrum of 28 281
Figure 3-29-1. 1H-1H COSY and HMBC correlations for 29 282
Figure 3-29-2. Key NOESY correlations for 29 283
Figure 3-29-3. ESIMS spectrum of 29 284
Figure 3-29-4. HRESIMS spectrum of 29 284
Figure 3-29-5. 1H NMR spectrum of 29 285
Figure 3-29-6. 13C NMR and DEPT spectra of 29 286
Figure 3-29-7. COSY spectrum of 29 287
Figure 3-29-8. HMQC spectrum of 29 287
Figure 3-29-9. HMBC spectrum of 29 288
Figure 3-29-10. NOESY spectrum of 29 288
Figure 3-30-1.化合物28進行還原反應 290
Figure 3-30-2. FABMS spectrum of 30 291
Figure 3-30-3. HRFABMS spectrum of 30 291
Figure 3-30-4. 1H NMR spectrum of 30 292
Figure 3-30-5. 13C NMR and DEPT spectra of 30 292
Figure 3-30-6. COSY spectrum of 30 293
Figure 3-30-7. HMQC spectrum of 30 293
Figure 3-30-8. HMBC spectrum of 30 294
Figure 3-31-1. 1H-1H COSY and HMBC correlations for 31 295
Figure 3-31-2. ESIMS spectrum of 31 297
Figure 3-31-3. HRESIMS spectrum of 31 297
Figure 3-31-4. 1H NMR spectrum of 31 298
Figure 3-31-5. 13C NMR spectrum of 31 298
Figure 3-31-6. COSY spectrum of 31 299
Figure 3-31-7. HMQC spectrum of 31 299
Figure 3-30-8. HMBC spectrum of 31 300
Figure 3-32-1. 1H-1H COSY and HMBC correlations for 32 302
Figure 3-32-2. Key NOESY correlations for 32 302
Figure 3-32-3. ESIMS spectrum of 32 304
Figure 3-32-4. HRESIMS spectrum of 32 304
Figure 3-32-5. 1H NMR spectrum of 32 305
Figure 3-32-6. 13C NMR and DEPT spectra of 32 305
Figure 3-32-7. COSY spectrum of 32 306
Figure 3-32-8. HMQC spectrum of 32 306
Figure 3-32-9. HMBC spectrum of 32 307
Figure 3-32-10. NOESY spectrum of 32 307
Figure 3-33-1. Key NOESY correlations for 33 309
Figure 3-33-2. ESIMS spectrum of 33 311
Figure 3-33-3. HRESIMS spectrum of 33 311
Figure 3-33-4. 1H NMR spectrum of 33 312
Figure 3-33-5. DEPT spectrum of 33 312
Figure 3-33-6. 13C NMR spectrum of 33 313
Figure 3-33-7. COSY spectrum of 33 313
Figure 3-33-8. HMQC spectrum of 33 314
Figure 3-33-9. HMBC spectrum of 33 314
Figure 3-33-10. NOESY spectrum of 33 315
Figure 3-34-1. 1H-1H COSY and HMBC correlations for 34 317
Figure 3-34-2. Key NOESY correlations for 34 317
Figure 3-34-3. ESIMS spectrum of 34 319
Figure 3-34-4. HRESIMS spectrum of 34 319
Figure 3-34-5. 1H NMR spectrum of 34 320
Figure 3-34-6. 13C NMR and DEPT spectra of 34 320
Figure 3-34-7. COSY spectrum of 34 321
Figure 3-34-8. HMQC spectrum of 34 321
Figure 3-34-9. HMBC spectrum of 34 322
Figure 3-34-10. NOESY spectrum of 34 322
Figure 3-35-1. 1H-1H COSY and HMBC correlations for 35 324
Figure 3-35-2. Key NOESY correlations for 35 324
Figure 3-35-3. ESIMS spectrum of 35 326
Figure 3-35-4. HRESIMS spectrum of 35 326
Figure 3-35-5. 1H NMR spectrum of 35 327
Figure 3-35-6. 13C NMR and DEPT spectra of 35 327
Figure 3-35-7. COSY spectrum of 35 328
Figure 3-35-8. HMQC spectrum of 35 328
Figure 3-35-9. HMBC spectrum of 35 329
Figure 3-35-10. NOESY spectrum of 35 329
Figure 3-36-1. 1H-1H COSY and HMBC correlations for 36 330
Figure 3-36-2. Key NOESY correlations for 36 331
Figure 3-36-3. ESIMS spectrum of 36 332
Figure 3-36-4. HRESIMS spectrum of 36 332
Figure 3-36-5. 1H NMR spectrum of 36 333
Figure 3-36-6. 13C NMR spectrum of 36 333
Figure 3-36-7. COSY spectrum of 36 334
Figure 3-36-8. HMQC spectrum of 36 334
Figure 3-36-9. HMBC spectrum of 36 335
Figure 3-36-10. NOESY spectrum of 36 335
Figure 3-37-1. 1H NMR spectrum of 37 336
Figure 3-37-2. 13C NMR spectrum of 37 337
Figure 3-38-1. 1H NMR spectrum of 38 337
Figure 3-38-2. 13C NMR spectrum of 38 338
Figure 3-39-1. 1H-1H COSY and HMBC correlations for 39 341
Figure 3-39-2. Selective NOE correlations for 39 341
Figure 3-39-3. X-ray crystal structure of 39 341
Figure 3-39-4. ESIMS spectrum of 39 343
Figure 3-39-5. HRESIMS spectrum of 39 343
Figure 3-39-6. 1H NMR spectrum of 39 344
Figure 3-39-7. 13C NMR and DEPT spectra of 39 345
Figure 3-39-8. COSY spectrum of 39 346
Figure 3-39-9. HMQC spectrum of 39 346
Figure 3-39-10. HMBC spectrum of 39 347
Figure 3-39-11. NOESY spectrum of 39 347
Figure 3-40-1. 1H-1H COSY and HMBC correlations for 40 348
Figure 3-40-2. Selective NOE correlations for 40 349
Figure 3-40-3. ESIMS spectrum of 40 350
Figure 3-40-4. HRESIMS spectrum of 40 350
Figure 3-40-5. 1H NMR spectrum of 40 351
Figure 3-40-6. 13C NMR and DEPT spectra of 40 352
Figure 3-40-7. COSY spectrum of 40 352
Figure 3-40-8. HMQC spectrum of 40 353
Figure 3-40-9. HMBC spectrum of 40 353
Figure 3-40-10. NOESY spectrum of 40 354
Figure 3-41-1. 1H-1H COSY and HMBC correlations for 41 355
Figure 3-41-2. Computer-generateprespective model for 41 using force field calculation
with selective NOE correlations 356
Figure 3-41-3. ESIMS spectrum of 41 357
Figure 3-41-4. HRESIMS spectrum of 41 357
Figure 3-41-5. 1H NMR spectrum of 41 358
Figure 3-41-6. 13C NMR and DEPT spectra of 41 359
Figure 3-41-7. COSY spectrum of 41 359
Figure 3-41-8. HMQC spectrum of 41 360
Figure 3-41-9. HMBC spectrum of 41 360
Figure 3-41-10. NOESY spectrum of 41 361
Figure 3-42-1. 1H-1H COSY and HMBC correlations for 42 362
Figure 3-42-2. Computer-generateprespective model for 42 using force field calculation
with selective NOE correlations 363
Figure 3-42-3. ESIMS spectrum of 42 364
Figure 3-42-4. HRESIMS spectrum of 42 364
Figure 3-42-5. 1H NMR spectrum of 42 365
Figure 3-42-6. 13C NMR and DEPT spectra of 42 366
Figure 3-42-7. COSY spectrum of 42 366
Figure 3-42-8. HMQC spectrum of 42 367
Figure 3-42-9. HMBC spectrum of 42 367
Figure 3-42-10. NOESY spectrum of 42 368
Figure 3-43-1. Key 1H-1H COSY, HMBC and NOESY correlations for 43 370
Figure 3-43-2. ESIMS spectrum of 43 371
Figure 3-43-3. HRESIMS spectrum of 43 371
Figure 3-43-4. 1H NMR spectrum of 43 372
Figure 3-43-5. 13C NMR and DEPT spectra of 43 372
Figure 3-43-6. COSY spectrum of 43 373
Figure 3-43-7. HMQC spectrum of 43 373
Figure 3-43-8. HMBC spectrum of 43 374
Figure 3-43-9. NOESY spectrum of 43 374
Figure 3-44-1. 13C NMR and DEPT spectra of 44 375
Figure 3-44-2. 1H NMR spectrum of 44 376
Figure 3-45-1. 13C NMR and DEPT spectra of 45 378
Figure 3-45-2. 1H NMR spectrum of 45 378
Figure 3-46-1. 1H NMR spectrum of 46 379
Figure 3-46-2. 13C NMR spectrum of 46 380
Figure 3-47-1. 1H-1H COSY and HMBC correlations for 47 382
Figure 3-47-2. Selective NOESY correlations of 47 382
Figure 3-47-3. EIMS spectrum of 47 384
Figure 3-47-4. HRESIMS spectrum of 47 384
Figure 3-47-5. 1H NMR spectrum of 47 385
Figure 3-47-6. 13C NMR spectrum of 47 386
Figure 3-47-7. COSY spectrum of 47 386
Figure 3-47-8. HMQC spectrum of 47 387
Figure 3-47-9. HMBC spectrum of 47 387
Figure 3-47-10. NOESY spectrum of 47 388
Figure 3-48-1. 1H-1H COSY and HMBC correlations for 48 391
Figure 3-48-2. Selective NOE correlations for 48 391
Figure 3-48-3. ESIMS spectrum of 48 393
Figure 3-48-4. HRESIMS spectrum of 48 393
Figure 3-48-5. 1H NMR spectrum of 48 394
Figure 3-48-6. 13C NMR and DEPT spectra of 48 395
Figure 3-48-7. COSY spectrum of 48 396
Figure 3-48-8. HMQC spectrum of 48 396
Figure 3-48-9. HMBC spectrum of 48 397
Figure 3-48-10. NOESY spectrum of 48 397
Figure 3-49-1. 1H-1H COSY and HMBC correlations for 49 399
Figure 3-49-2. Selective NOE correlations for 49 399
Figure 3-49-3. ESIMS spectrum of 49 401
Figure 3-49-4. HRESIMS spectrum of 49 401
Figure 3-49-5. 1H NMR spectrum of 49 402
Figure 3-49-6. 13C NMR and DEPT spectra of 49 403
Figure 3-49-7. COSY spectrum of 49 404
Figure 3-49-8. HMQC spectrum of 49 404
Figure 3-49-9. HMBC spectrum of 49 405
Figure 3-49-10. NOESY spectrum of 49 405
Figure 3-50-1. 1H-1H COSY and HMBC correlations for 50 407
Figure 3-50-2. Selective NOE correlations for 50 407
Figure 3-50-3. ESIMS spectrum of 50 409
Figure 3-50-4. HRESIMS spectrum of 50 409
Figure 3-50-5. 1H NMR spectrum of 50 410
Figure 3-50-6. 13C NMR and DEPT spectra of 50 411
Figure 3-50-7. COSY spectrum of 50 412
Figure 3-50-8. HMQC spectrum of 50 412
Figure 3-50-9. HMBC spectrum of 50 413
Figure 3-50-10. NOESY spectrum of 50 413
Figure 3-51-1. 1H NMR spectrum of 51 414
Figure 3-51-1. 13C NMR spectrum of 51 415
Figure 3-52-1. 1H NMR spectrum of 52 416
Figure 3-52-1. 13C NMR spectrum of 52 417
Figure 3-53-1. 1H NMR spectrum of 53 418
Figure 3-53-1. 13C NMR spectrum of 53 419
Figure 3-54-1. 1H NMR spectrum of 54 420
Figure 3-54-1. 13C NMR spectrum of 54 421
Figure 3-55-1. 1H NMR spectrum of 55 422
Figure 3-55-1. 13C NMR spectrum of 55 423





















表目錄

頁次
Table 1-1-1. Status of Marine-Derived Natural Products in Clinical and Preclinical Trials 10
Table 1-2-1. 台灣產的軟珊瑚Cespitularia taeniata所含天然物的文獻報告 15
Table 1-2-2. 台灣產的軟珊瑚Cespitularia hypotentaculata所含天然物的文獻報告
16
Table 1-2-3. 台灣產的軟珊瑚Cladiella australis所含天然物的文獻報告 17
Table 1-2-4. 台灣產的軟珊瑚Dendronephthya gigantea所含天然物的文獻報告 18
Table 1-2-5. 台灣產的軟珊瑚Lemnalia cervicorni所含天然物的文獻報告 18
Table 1-2-6. 台灣產的軟珊瑚Lemnalia laevis所含天然物的文獻報告 19
Table 1-2-7. 台灣產的軟珊瑚Lobophytum michaelae所含天然物的文獻報告 20
Table 1-2-8. 台灣產的軟珊瑚Lobophytum mirabile所含天然物的文獻報告 20
Table 1-2-9. 台灣產的軟珊瑚Loboohytum crassum所含天然物的文獻報告 20
Table 1-2-10. 台灣產的軟珊瑚Nephthea armata所含天然物的文獻報告 21
Table 1-2-11. 台灣產的軟珊瑚Nephthea brassica所含天然物的文獻報告 22
Table 1-2-12. 台灣產的軟珊瑚Nephthea erecta所含天然物的文獻報告 23
Table 1-2-13. 台灣產的軟珊瑚Nephthea pacifica所含天然物的文獻報告 24
Table 1-2-14. 台灣產的軟珊瑚Paralemnalia thyrsoides所含天然物的文獻報告 25
Table 1-2-15. 台灣產的軟珊瑚Sarcophyton crassocaule所含天然物的文獻報告 25
Table 1-2-16. 台灣產的軟珊瑚Sarcophyton glaucum所含天然物的文獻報告 26
Table 1-2-17. 台灣產的軟珊瑚Sarcophyton trocheliphorum所含天然物的文獻報告 26
Table 1-2-18. 台灣產的軟珊瑚Siunlaria flexibilis所含天然物的文獻報告 27
Table 1-2-19. 台灣產的軟珊瑚Siunlaria gibberosa所含天然物的文獻報告 28
Table 1-2-20. 台灣產的軟珊瑚Siunlaria inelegans所含天然物的文獻報告 30
Table 1-2-21. 台灣產的軟珊瑚Siunlaria lochmodes所含天然物的文獻報告 30
Table 1-2-22. 台灣產的軟珊瑚Siunlaria letoclados所含天然物的文獻報告 31
Table 1-2-23. 台灣產的軟珊瑚Siunlaria nanolobata所含天然物的文獻報告 32
Table 1-2-24. 台灣產的軟珊瑚Siunlaria polydactyla所含天然物的文獻報告 32
Table 1-2-25. 台灣產的軟珊瑚Siunlaria parva所含天然物的文獻報告 33
Table 1-2-26. 台灣產的軟珊瑚Siunlaria scabra所含天然物的文獻報告 33
Table 1-2-27. 台灣產的軟珊瑚Siunlaria sp.所含天然物的文獻報告 35
Table 1-2-28. 台灣產的軟珊瑚Stereonephthya crystalliana所含天然物的文獻報告 37
Table 1-2-29. 台灣產的軟珊瑚Xenia blumi所含天然物的文獻報告 38
Table 1-2-30. 台灣產的軟珊瑚Xenia florida所含天然物的文獻報告 39
Table 1-2-31. 台灣產的軟珊瑚Xenia puerto-galerae所含天然物的文獻報告 40
Table 1-2-32. 台灣產的軟珊瑚Xenia umbellata所含天然物的文獻報告 41
Table 1-2-33. 台灣產的柳珊瑚Briareum excavatum所含天然物的文獻報告 45
Table 1-2-34. 台灣產的柳珊瑚Briareum sp.所含天然物的文獻報告 50
Table 1-2-35. 台灣產的柳珊瑚Isis hippuris所含天然物的文獻報告 51
Table 1-2-36. 台灣產的柳珊瑚Junceella juncea所含天然物的文獻報告 55
Table 1-2-37. 台灣產的柳珊瑚Junceella fragilis所含天然物的文獻報告 56
Table 1-2-38. 台灣產的柳珊瑚subergorgia mollis所含天然物的文獻報告 58
Table 1-2-39. 台灣產的柳珊瑚subergorgia suberosa所含天然物的文獻報告 58
Table 1-2-40. 台灣產的羽珊瑚Clavularia inflata所含天然物的文獻報告 61
Table 1-2-41. 台灣產的羽珊瑚Clavularia violacea所含天然物的文獻報告 62
Table 1-2-42. 台灣產的羽珊瑚Clavularia viridis所含天然物的文獻報告 62
Table 1-2-43. 台灣產的軟珊瑚Tubipora musica所含天然物的文獻報告 64
Table 1-2-44. 台灣產的軟珊瑚Pachyclavularia violacea所含天然物的文獻報告 65
Table 1-2-45. 台灣產的海筆珊瑚Virgularia juncea所含天然物的文獻報告 67
Table 3-1-1. 1H and 13C NMR Data for Compound 1 113
Table 3-2-1. 1H and 13C NMR Data for Compound 2 121
Table 3-3-1. 1H and 13C NMR Data for Compound 3 127
Table 3-4-1. 1H and 13C NMR Data for Compound 4 133
Table 3-5-1. 1H and 13C NMR Data for Compounds 5 and 4 139
Table 3-6-1. 1H and 13C NMR Data for Compound 6 145
Table 3-7-1. 1H and 13C NMR Data for Compound 7 151
Table 3-8-1. 1H and 13C NMR Data for Compound 8 157
Table 3-9-1. 1H and 13C NMR Data for Compound 9 163
Table 3-10-1. 1H and 13C NMR Data for Compound 10 169
Table 3-11-1. 1H and 13C NMR Data for Compounds 11 and 4 175
Table 3-12-1. 1H and 13C NMR Data for Compound 12 181
Table 3-13-1. 1H and 13C NMR Data for Compounds 13 and 6 187
Table 3-14-1. 1H and 13C NMR Data for Compound 14 193
Table 3-15-1. 1H and 13C NMR Data for Compound 15 199
Table 3-16-1. 1H and 13C NMR Data for Compound 16 205
Table 3-17-1. 1H and 13C NMR Data for Compound 17 211
Table 3-18-1. 1H and 13C NMR Data for Compound 18 217
Table 3-20-1. 1H and 13C NMR Data for Compounds 20 and 1 225
Table 3-21-1. 1H and 13C NMR Data for Compounds 20 and 21 231
Table 3-22-1. 1H and 13C NMR Data for Compound 22 237
Table 3-23-1. 1H and 13C NMR Data for Compound 23 244
Table 3-24-1. 1H and 13C NMR Data for Compound 24 251
Table 3-26-1. 1H and 13C NMR Data for Compound 26 260
Table 3-27-1. 1H and 13C NMR Data for Compound 27 267
Table 3-28-1. 1H and 13C NMR Data for Compound 28 276
Table 3-29-1. 1H and 13C NMR Data for Compound 29 283
Table 3-30-1. 1H and 13C NMR Data for Compound 30 290
Table 3-31-1. 1H and 13C NMR Data for Compounds 30 and 31 296
Table 3-32-1. 1H and 13C NMR Data for Compound 32 303
Table 3-33-1. 1H and 13C NMR Data for Compound 33 310
Table 3-34-1. 1H and 13C NMR Data for Compound 34 318
Table 3-35-1. 1H and 13C NMR Data for Compound 35 325
Table 3-36-1. 1H and 13C NMR Data for Compound 36 331
Table 3-39-1. 1H and 13C NMR Data for Compound 39 342
Table 3-40-1. 1H and 13C NMR Data for Compound 40 349
Table 3-41-1. 1H and 13C NMR Data for Compound 41 356
Table 3-42-1. 1H and 13C NMR Data for Compound 32 363
Table 3-43-1. 1H and 13C NMR Data for Compounds 43 and 23 370
Table 3-47-1. 1H and 13C NMR Data for Compound 47 383
Table 3-48-1. 1H and 13C NMR Data for Compound 48 392
Table 3-49-1. 1H and 13C NMR Data for Compound 49 400
Table 3-50-1. 1H and 13C NMR Data for Compound 50 408
Table 4-2-1. 化合物在20 μg/mL濃度下對三種癌細胞之細胞毒殺活性數值 425
Table 4-2-2. 化合物對四種癌細胞之細胞毒殺活性數值 427
Table 4-2-3. 化合物對三種癌細胞之細胞毒殺活性數值 427

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