本研究主要是從軟珊瑚Klyxum simplex、Subergorgia mollis與Briareum excavatum的有機萃取物中找尋具有生物活性的化學成分。從這三種珊瑚的研究中共得到二十七個天然化合物 (1–27)，其中從軟珊瑚K. simplex中分離出十九個新的eunicellin– type diterpenoids類化合物simplexins A–S (1–19)，從軟珊瑚S. mollis中分離出一個新的pregnane類化合物11α,15α-diacetoxy-17β-pregna-4,20-dien-3-one (20)和一個已知化合物17β-pregna-4,20-dien-3-one (21) ，另外從軟珊瑚B. excavatum中分離出六個新的briarane–type diterpenoids類化合物briaexcavatolide Q (22), S–V (23-26), W(27)。所有化合物的化學構造均由光譜數據的分析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決定。另經由一種修飾後之Mosher酯化反應，可確定化合物1的絕對立體構造。
本研究中也將所獲得的化合物1–6, 9, 13–15進行癌細胞株的細胞毒殺活性測試與抗發炎活性測試。在細胞毒殺活性測試結果顯示化合物1、4及14對MCF-7(人類乳癌細胞)、Hep2(人類喉癌細胞)和Daoy(人類髓母細胞瘤癌細胞)有弱的活性，但對Hela(人類子宮頸癌細胞)無活性，而化合物5對四種癌細胞皆有弱的細胞毒殺活性。在抗發炎活性測試結果顯示，化合物5有最強的抗發炎活性。

In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of one soft corals Klyxum simplex and two gorgonians Subergorgia mollis and Briareum excavatum. This study had led to the isolation of twenty-seven natural compounds 1–27, including nineteen new eunicellin–type diterpenoids, simplexins A–S (1–19) from K. simplex, one new steroid 11α,15α-diacetoxy-17β-pregna-4,20- dien-3-one (20) along with one known compound 17β-pregna-4,20-dien-3- one (21) from S. mollis, and six new briarane–type diterpenoids briaexcavatolides Q (22), S–V (23-26) and W (27) from B. excavatum. The structure of these compounds were established by the detailed spectroscopic analysis (IR, MS, 1D、2D NMR) and by comparison of the physical and spectral data with those of the related known compounds. The absolute configuration of 1 was determined by using a modified Mosher's method.
The cytotoxicity of compounds 1–6, 9, 13–15 against the MCF-7 (human breast adenocarcinoma), Hep2 (human laryngeal carcinoma), Daoy (human medulloblastoma), and Hela (human cervical epitheloid carcinoma) cancer cell lines were determined. Compounds 1, 4 and 14 showed weak inhibition against the growth of MCF-7, Hep2 and Daoy, but did not inhibit the growth of Hela cells. Compound 5 exhibited a weak cytotoxicity against the growth of MCF-7, Hep2, Hela and Daoy cells. In addition, the activity of compounds 1–6, 9, 13–15 to inhibit the pro-inflammatory iNOS and COX-2 protein expression in LPS-stimulated RAW264.7 macrophage cells was estimated. Compound 5 showed the best anti-inflammatory activity among the all tested compounds.

目 錄 頁 次
中文摘要 XV
英文摘要 XVI
化合物1-27化學構造 XVII
壹、緒論 1
一、研究背景及目的 1
二、Klyxum屬所含天然物的文獻回顧 4
三、Subergorgia屬所含天然物的文獻回顧 39
四、Briareum屬所含天然物的文獻回顧 48
貳、生物材料與研究方法 94
一、研究流程 94
二、Klyxum simplex Thomson and Dean物種的採集及分類地位 95
三、K. simplex軟珊瑚的分離流程 96
四、Subergorgia mollis Nutting物種的採集及分類地位 98
五、S. mollis軟珊瑚的分離流程 99
六、Briareum excavatum Nutting物種的採集及分類地位 100
七、B. excavatum軟珊瑚的分離流程 101
八、Mosher’s酯化反應－決定化合物的絕對立體組態 104
九、實驗器材與溶劑 105
參、實驗結果與化學構造解析 107
一、軟珊瑚K. simplex分離之化合物 107
(一)、Simplexin A (1) 化學構造之解析 109
(二)、Simplexin B (2) 化學構造之解析 119
(三)、Simplexin C (3) 化學構造之解析 129
(四)、Simplexin D (4) 化學構造之解析 139
(五)、Simplexin E (5) 化學構造之解析 147
(六)、Simplexin F (6) 化學構造之解析 157
(七)、Simplexin G (7) 化學構造之解析 166
(八)、Simplexin H (8) 化學構造之解析 175
(九)、Simplexin I (9) 化學構造之解析 183
(十)、Simplexin J (10) 化學構造之解析 193
(十一)、Simplexin K (11) 化學構造之解析 202
(十二)、Simplexin L (12) 化學構造之解析 211
(十三)、Simplexin M (13) 化學構造之解析 220
(十四)、Simplexin N (14) 化學構造之解析 228
(十五)、Simplexin O (15) 化學構造之解析 236
(十六)、Simplexin P (16) 化學構造之解析 245
(十七)、Simplexin Q (17) 化學構造之解析 254
(十八)、Simplexin R (18) 化學構造之解析 263
(十九)、Simplexin S (19) 化學構造之解析 272
二、軟珊瑚S. mollis分離之化合物 281
(二十)、11α,15α-Diacetoxy-17β-pregna-4,20-dien-3-one (20) 化學構造之解析 282
(二十一)、17β-Pregna-4,20-dien-3-one (21) 化學構造之解析 290
三、軟珊瑚B. excavatum分離之化合物 294
(二十二)、Briaexcavatolide Q (22) 化學構造之解析 295
(二十三)、Briaexcavatolide S (23) 化學構造之解析 304
(二十四)、Briaexcavatolide T (24) 化學構造之解析 313
(二十五)、Briaexcavatolide U (25) 化學構造之解析 321
(二十六)、Briaexcavatolide V (26) 化學構造之解析 330
(二十七)、Briaexcavatolide W (27) 化學構造之解析 339
肆、生物活性試驗 348
一、生物活性試驗 348
(一)、細胞毒殺活性試驗 348
(二)、抗發炎活性試驗 349
二、生物活性試驗結果 350
(一)、細胞毒殺活性試驗結果 350
(二)、抗發炎活性試驗結果 351
伍、結論 355
陸、化合物之物理及圖譜數據 358
柒、參考文獻 363

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