本論文的研究主要從1種海綿Dysidea sp.的萃取物中尋找海洋天然化合物，從這種海綿Dysidea sp.共得到5個brominated diphenyl ethers類的天然化合物，3,5-dibromo-2-(2',4'-dibromophenoxy)phenol (1)， 3,5,6-tribromo-2-(2',4'-dibromophenoxy)phenol (2)，6-chloro-3,5-dibromo-2-(2',4'-dibromophenoxy)phenol (3)， 3,4,5-tribromo-2-(2',4'-dibromophenoxy)phenol (4) and 3,5-tribromo-4-chloro-2-(2',4'-dibromophenoxy)phenol (5)。這5個天然物的化學結構是經由NMR圖譜解析而得到。此外天然物1, 4和5更進一步經由X-ray晶體繞射來證明其化合物之結構。
本論文中將所分離純化之的天然物1–5針對3種人類癌細胞human breast adenocarcinoma (MCF-7)、human oral cancer cells (SCC2095) 和human gastric cancer cells (SCM1)進行細胞毒殺活性測試。結果顯示化合物1及3對human oral cancer cells具有微弱的細胞毒殺活性 (IC50值為 26.9 ± 7.7 and 23.9 ± 3.0 μM)，而其它化合物對以上三種癌細胞均無細胞毒殺活性(IC50值>30 μM)。

We have studied the marine natural products from the EtOAc extracts of the sponge Dysidea sp. This study led to the isolation of five brominated diphenyl ethers natural compounds, 3,5-dibromo-2-(2',4'-dibromophenoxy)phenol (1), 3,5,6-tribromo-2-(2',4'-dibromophenoxy)phenol (2), 6-chloro-3,5-dibromo-2-(2',4'-dibromophenoxy)phenol (3), 3,4,5-tribromo-2-(2',4'-dibromophenoxy)phenol (4) and 3,5-tribromo-4-chloro-2-(2',4'-dibromophenoxy)phenol (5) from the sponge Dysidea sp. The structure of marine brominated diphenyl ethers 1–5 were established by detailed NMR spectral data analysis. Moreover, the structure of natural products 1, 4 and 5 were further confirmed by X-ray single-crystal diffraction analysis.
The cytotoxicity of compounds 1–5 against the human breast adenocarcinoma (MCF-7), human oral cancer cells (SCC2095) and human gastric cancer cells (SCM1) were determined. The results showed that two compounds 1 and 3 exhibited weak against the proliferation of SCC2095 cells (IC50 26.9 ± 7.7 and 23.9 ± 3.0 μM) and other metabolites were inactive (IC50 >30 μM) towards these cancer cell lines.

第一章 緒論 1
第一節 前言與研究動機 1
第二節 Dysidea屬海綿所含天然物之文獻探討 2
第三節 多溴二苯醚類PBDEs介紹 7
第二章 生物材料與分離流程 11
第一節 生物樣本採集與分類 11
第二節 生物樣品萃取與分離流程 12
第三章 實驗器材與有機溶劑 15
第一節 儀器 15
第二節 其他材料與有機溶劑 17
第四章 結果與討論 19
1.3,5-dibromo-2-(2',4'-dibromophenoxy)phenol (1) 之結構解析 19
2.3,5,6-tribromo-2-(2',4'-dibromophenoxy)phenol (2) 之結構解析 30
3.6-chloro-3,5-dibromo-2-(2',4'-dibromophenoxy)phenol (3) 之結構解析 39
4.3,4,5-tribromo-2-(2',4'-dibromophenoxy)phenol (4) 及3,5-tribromo-4-chloro-2-(2',4'-dibromophenoxy)phenol (5) 之結構解析 48
第五章 生物活性試驗 51
第一節 細胞毒殺活性 51
第二節 細胞毒殺活性結果 52
第六章 結論 53
參考文獻 55
附錄一 化合物 1 之X-ray 實驗數據 59
附錄二 化合物4和5之X-ray 實驗數據 65

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