最近幾年海洋生物被認為是最有潛力開發新藥物的來源，其中由軟珊瑚發現許多的活性二次代謝物，部份二次代謝物也已經在做藥理測試。為了從台灣海域的軟珊瑚開發新的藥物，我們針對二種軟珊瑚Sinularia gibberosa、 Sarcophyton sp. 的有機萃取物來找尋活性物質。從上述兩種珊瑚的研究分析共得到四十二個化合物 (1–42)，其中從軟珊瑚Sinularia gibberosa中分離出二十七個新的天然化合物1–27和五個已知的化合物28–32；在這些新的天然物中化合物1屬於β-caryophyllene-type sesquiterpenoid，化合物2、14、16和17屬於xeniaphyllane-type norditerpenoids，化合物3–13和18–20屬於 xeniaphyllane-type diterpenoids，化合物15屬於nor-humulene，化合物21-26屬於含有peroxyhemiketal的xeniaphyllane-type diterpenoids，化合物27屬於steroid，與五個已知的天然化合物28–32。另外從軟珊瑚Sarcophyton sp.中分離出十個cembrane類的天然化合物，其中有3個新的天然化合物33–35與七個已知的天然化合物36–42。
上述化合物之細胞毒殺活性測試結果顯示，化合物 8、9 對 (MCF-7、Hep 3B 和 Ca9-22) 癌細胞有毒殺活性，化合物 4、8、9、11、12、13、21、31、39 對 (MDA-MB-231、Hep G2 和 A-549) 癌細胞也有細胞毒殺活性。

Marine organisms have attracted much attention as potential source for drugs over recent years. Soft corals have yielded many bioactive metabolites. Some of them have been examined for their pharmacological properties. For the process of drug discovery, we have examined bioactive metabolites from the organic extracts of two soft corals Sinularia gibberosa and Sarcophyton sp. collected off Formosan coast. This study had led to the isolation of forty-two natural products (1–42), including one new β-caryophyllene-type sesquiterpenoid (1), four new xeniaphyllane-type norditerpenoids (2, 14, 16, and 17), fourteen new xeniaphyllane-type diterpenoids (3–13 and 18–20), one novel nor-humulene (15), seven new xeniaphyllane-type diterpenoids (21–26) with cyclic peroxyhemiketal (3,6-dihydro-1,2-dioxin-3-ol) moiety, and one new steroid (27), along with five known compounds (28–32) from Sinularia gibberosa. Three new cembrane-type diterpenoids (33–35), along with seven known cembranolides (36–42) were isolated from Sarcophyton sp. The structures of metabolites 1–42 including their stereochemistry 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 from other known compounds.
In above metabolites, two compounds (8, 9) exhibited cytotoxicity against the growth of MCF-7, Hep 3B, Ca9-22 cancer cell lines. Furthermore, nine compounds (4, 8, 9, 11, 12, 13, 21, 31, 39) exhibited cytotoxicity against the growth of MDA-MB-231, Hep G2 and A-549 cancer cell lines.

頁次
摘要 1
英文摘要 2
化合物1-42的結構 3
壹、研究動機 6
一、 研究之動機及目的 6
二、 文獻回顧 10
(一) Sinularia屬的24種珊瑚所含天然化合物及其生物活性的回顧 13
(二) Sarcophyton屬的7種珊瑚所含天然化合物及其生物活性的回顧 36
(三) Xenia屬軟珊瑚以及Xeniaphyllane類的天然化合物及其活性回顧 43
貳、實驗流程與方法
一、 實驗流程 57
二、 Sinularia gibberosa之基本資料及分離流程 58
(一) Sinularia gibberosa樣品採集時間、地點、分類地位 58
(二) Sinularia gibberosa樣品的萃取分離 58
三、 Sarcophyton sp.之基本資料及分離流程 60
(一) Sarcophyton sp.樣品採集時間、地點、分類地位 60
(二) Sarcophyton sp.樣品的萃取分離 60
四、 實驗設備儀器及材料 62
(一) 實驗設備儀器 62
(二) 實驗材料 63


參、化合物之結構解析
一、 軟珊瑚Sinularia gibberosa所分離出之化合物的化學結構解析 64
(一) Methyl-(1S*,4S*,5S*,9R*,11S*)- 4,5-epoxycaryophyllen-13-oate
(1) 的化學結構解析 66
(二) Gibberosin A (2)的化學結構解析 73
(三) Gibberosin B (3)的化學結構解析 80
(四) Gibberosin C (4)的化學結構解析 87
(五) Gibberosin D (5)的化學結構解析 94
(六) Gibberosin E (6)的化學結構解析 101
(七) Gibberosin F (7)的化學結構解析 108
(八) Gibberosin G (8)的化學結構解析 115
(九) Gibberosin H (9)的化學結構解析 122
(十) Gibberosin I (10)的化學結構解析 129
(十一) Gibberosin J (11)的化學結構解析 136
(十二) Gibberosin K (12)的化學結構解析 143
(十三) Gibberosin L (13)的化學結構解析 150
(十四) Gibberosin M (14)的化學結構解析 157
(十五) Gibberosin N (15)的化學結構解析 164
(十六) Gibberosin O (16)的化學結構解析 171
(十七) Gibberosin P (17)的化學結構解析 178
(十八) Gibberosin Q (18)的化學結構解析 185
(十九) Gibberosin R (19)的化學結構解析 192
(二十) Gibberosin S (20)的化學結構解析 199
(二十一) Sinugibberoside A (21)的化學結構解析 206
(二十二) Sinugibberoside B (22)的化學結構解析 214
(二十三) Sinugibberoside C (23)的化學結構解析 221
(二十四) Sinugibberoside D (24)的化學結構解析 228
(二十五) Sinugibberoside E (25)的化學結構解析 235
(二十六) Sinugibberoside F (26)的化學結構解析 242
(二十七) 5, 22, 24 (28)-Ergostatriene-3β-ol (27)的化學結構解析 250
(二十八) Nanonorcaryophyllene A (28)的化學結構解析 258
(二十九) 4,5-Epoxycaryophyll-8(14)-en-12-oic acid (29)
的化學結構解析 261
(三十) Nanolobatin A (30)的化學結構解析 264
(三十一) Nanolobatin B (31)的化學結構解析 267
(三十二) Nanolobatin C (32)的化學結構解析 270
二、 軟珊瑚 Sarcophyton sp.所分離出之化合物的化學結構解析 273
(三十三) Sarcophtonin D (33)的化學結構解析 274
(三十四) Sarcophtonin E (34)的化學結構解析 282
(三十五) Sarcophtonin F (35)的化學結構解析 290
(三十六) 15-Hydroxycembra-1,3,7,11-tetraene (36)的化學結構解析 297
(三十七) Sarcophtonin C (37)的化學結構解析 300
(三十八) Sarcophine (38)的化學結構解析 303
(三十九) Sarcophytoxide (39)的化學結構解析 306
(四十) Sarcophtonin A (40)的化學結構解析 309
(四十一) Isoneocembrene A (41)的化學結構解析 312
(四十二) (+)-3,4-Epoxycembrene A (42)的化學結構解析 315
肆、細胞毒殺活性試驗
一、 細胞毒殺活性檢測方法 318
二、 細胞毒殺活性檢測結果 319
伍、結論 321
陸、化合物之物理性質 324
柒、Mosher酯化反應(決定絕對立體位向) 331
捌、參考資料 332

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