本研究是針對兩株軟珊瑚 Sinularia scabra 與 Lemnalia flava 的有機萃取物尋找具有生物活性的化學成分。從這兩株軟珊瑚中一共得到八個天然化合物1–8，其中從軟珊瑚Sinularia sacbra中分離出兩個新的 sesquiterpenoids 類之化合物，scabralin A (1)與 scabralin B (2)， 以及兩個已知化合物 3、4。從軟珊瑚 Lemnalia flava 中分離出兩個新的 sesquiterpenoids 類化合物，flavalin A (5)與 flavalin B (6)，以及三個已知化合物(4, 7, 8)。以上化合物的化學構造都由光譜數據的分析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決定。
另外將在養殖型軟珊瑚Lobophytum crassum 中大量取得的已知化合物Lobohedleolide (9) 經由 EDC-coupling 進行酯化反應，過程中添加 DMAP 的鹽酸鹽類提高產率，經過化學修飾後得到了化合物10–19。
本研究中將所獲得的化合物1、3–8和反應後的產物10–19進行癌細胞株的細胞毒殺與抗發炎活性測試。在細胞毒殺活性測試結果顯示化合物1對人類乳癌細胞(MCF-7)、人類結腸癌細胞(WiDr)、人類髓母細胞瘤癌細胞(Daoy)、人類喉癌細胞(Hep2)、人類急性淋巴細胞白血病T淋巴細胞(CCRF-CEM)都具有中等的細胞毒殺活性；經過化學修飾之化合物15、16對於人類肝癌細胞(Hep G2)具有中等的細胞毒殺活性，化合物10、12–14、17–18則有微弱的活性；化合物10、12、16–18對於 CCRF-CEM 具有中等的細胞毒殺活性；而化合物10、16、18對於人類結直腸腫瘤細胞(DLD-1)則有微弱的細胞毒殺活性。此外化合物10、12、14–19對於在濃度為10 μM下可以有效的抑制發炎蛋白質 iNOS 的表現。

Marine invertebrates have been found to be a rich source of bioactive secondary metabolites. In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of two Formosan soft corals, Sinularia Scabra and Lemnalia flava. This study had led to the isolation of eight natural compounds, including two new sesquiterpenoids, scabralin A (1) and scabralin B (2) along with two known compounds (3 and 4) from Sinularia scabra, and two new sesquiterpenoids, flavalin A (5) and flavalin B (6) along with three known compounds (4, 7 and 8) from Lemnalia flava. The structures of these compounds were established by the detailed spectral analysis (IR, MS, 1D, 2D NMR) and by comparison of the spectral data with the related known compounds.
Lobohedleolide (9), with a great quantity in Lobophytum crassum, have also been modified to compounds 10−19 by chemical conversions with the corresponding reactants via EDC-coupling with an aid of HCl salt of DMAP to yield the related esters and amides.The cytotoxicity of compounds 1, 3−8 and 10–19 against the MCF-7 (human breast adenocarcinoma), WiDr (Human colon adenocarcinoma), Daoy (human medulloblastoma), Hep2 (human laryngeal carcinoma), Hep G2 (human liver carcinoma), CCRF-CEM (human T-cell acute lymphoblastic leukemia), and DLD-1 (human colon adenocarcinoma) tumor cell lines were determined. Compound 1 showed moderate activity against the growth of Daoy, Hep2, MCF-7, Hela and CCRF-CEM. Both 15 and 16 exhibited a moderate cytotoxicity against the growth of Hep G2, and compounds 10, 12–14, 17 and 18 showed a weak cytotoxicity of it. Compounds 10, 12 and 16–18 were found to exhibit moderate inhibition against the growth of CCRF-CEM. Compounds 10, 16 and 18 showed weak activity against the growth of DLD-1. Furthermore, compounds 10, 12 and 14-19 were found to show significant activity against the accumulation of the pro-inflammatory iNOS protein at 10 μM.

中文摘要 XII
英文摘要 XIII
天然化合物1-9結構圖 XV
反應流程圖 XVI
第一章、緒論 1
第一節、前言 1
第二節、研究背景與動機 2
第三節、文獻回顧 4
第二章、生物材料與研究方法 23
第一節、實驗設備及材料 23
2-1-1 實驗設備儀器 23
2-1-2 實驗材料 24
第二節、研究流程 26
第三節：樣品之採樣與萃取分離 28
2-3-1 Sinularia scabra 樣品採集時間、地點、分類地位 28
2-3-2 Sinularia scabra 樣品的萃取與分離 29
2-3-3 Lemnalia flava 樣品採集時間、地點、分類地位 31
2-3-4 Lemnalia flava 樣品的萃取與分離 32
2-3-5 Lobophytum crassum珊瑚樣品的採集 34
2-3-6 Lobophytum crassum 樣品的萃取與分離 35
第四節、化學反應步驟 36
2-4-1 化合物10-19化學反應之機制 36
2-4-2 製備化合物10-19 36
第三章、化合物之結構證明
第一節：軟珊瑚 Sinularia scabra 所分離出之化合物的結構證明 41
(一)、Scabralin A (1)化合物構造之解析 41
(二)、Scabralin B (2)化合物構造之解析 51
(三)、(5’E)-5-(2’,6’-Dimethylocta-5’,7’-dienyl)furan-3-carboxylic acid (3)化合物構造之解析 60
(四)、1β-Hydroxy-6α-acetoxy-eudesm-4(15)-ene (4)化合物構造之解析 64
第二節：軟珊瑚Lemnalia flava 所分離出之化合物的結構證明 68
（五）、Flavalin A (5)化合物構造之解析 68
（六）、Flavalin B(6)化合物構造之解析 77
（七）、Lemnacarnol (7)化合物構造之解析 85
（八）、2-Oxolemnacarnol (8)化合物構造之解析 89
第三節：Lobohedleolide 之化學修飾結構 93
(九)、Lobohedleolide (9)之結構解析 93
(十)、Ethyl-lobohedleolide (10)之結構解析 97
(十一)、n-Propyl-lobohedleolide (11)之結構解析 103
(十二)、n-Butyl-lobohedleolide (12)之結構解析 109
(十三)、2S-Lobohedleolide-α-aminopropionic acid methyl ester (13)之結構解析 115
(十四)、Lobohedleolide-β-aminopropionic acid ethyl ester (14)之結構解析 122
(十五)、Lobohedleolide-aminoacetic acid ethyl ester (15)之結構解析 128
(十六)、2S-Lobohedleolide-α-aminopropionic acid ethyl ester (16)之結構解析 135
(十七)、Benzyl-lobohedleoamide (17)之結構解析 141
(十八)、Phenylmethyl-lobohedleolide (18)之結構解析 147
(十九)、Isopropyl-lobohedleoamide (19)之結構解析 153
第四章、生物活性篩檢試驗
第一節、生物活性篩檢試驗方法 159
(一)、細胞毒殺活性篩檢方法 159
(二)、抗發炎活性試驗方法 162
第二節、生物活性篩檢試驗結果 164
(一)、細胞毒殺活性篩結果 164
(二)、抗發炎活性試驗結果 167
第五章、結論 170
第六章、參考文獻 173
附錄一、化合物7之 X-ray 實驗數據 180

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