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博碩士論文 etd-1213101-171613 詳細資訊
Title page for etd-1213101-171613
論文名稱
Title
臺灣南部海域軟珊瑚Pachyclavularia violacea與Subergorgia suberosa所含天然化合物之研究
S法tudy on the Natural Products from the Formosan Soft Corals Pachyclavularia violacea and Subergorgia suberosa
系所名稱
Department
畢業學年期
Year, semester
語文別
Language
學位類別
Degree
頁數
Number of pages
363
研究生
Author
指導教授
Advisor
召集委員
Convenor
口試委員
Advisory Committee
口試日期
Date of Exam
2002-11-05
繳交日期
Date of Submission
2001-12-13
關鍵字
Keywords
細胞毒殺活性、天然物、軟珊瑚
soft corals, cyctotoxity, Pachyclavularia violacea, Subergorgia suberosa, natural products
統計
Statistics
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The thesis/dissertation has been browsed 5689 times, has been downloaded 1486 times.
中文摘要
為了尋找海洋軟珊瑚中活性天然成分,於是調查台灣墾丁國家公園海域所採集的軟珊瑚Pachyclavularia vilacea與Subergorgia suberosa,因為這兩種軟珊瑚的乙酸乙酯粗萃取液具有顯著的細胞毒殺活性值 (Table 1)。針對 P. vilacea 與 S. suberosa 所具有的化學成份研究中,共分離純化出 40 個化合物。於軟珊瑚 P. violacea總共分離得到25個化合物,其中有21個為新天然化合物,分為pachyclavulariolide G (1)、pachyclavulariolide H (3)、pachyclavulariolide I (4)、pachyclavulariolides J–S (6–15)、pachyclavulariaenones A–G (16–22)、secopachyclavulariaenone A (23) 。另外4個為已知的天然化合物,分別為pachyclavulariolide (2)、pachyclavulariolide E (5)、pachyclavulariolide A (24) 與 pachyclavulariolide B (25)。
此外在軟珊瑚S. suberosa中也分離純化出15個天然化合物,其中包含6個新天然化合物,分別為2b-acetoxysubergorgic acid (27)、subergorgiol (31)、suberosols A–D (34–37)。另外9個為已知的天然化合物,分別為 subergorgic acid (26)、2b-hydroxysubergorgic acid (28)、methyl ester of subergorgic acid (29)、2b-acetoxy methyl ester of subergorgic acid (30)、buddledin D (32)、buddledin C (33)、5b-pregnan-3,20-dione (38)、Δ1-5b- pregnen-3,20-dione (39)與3a-acetoxy- 5b-pregnan-20-one (40),化合物 39、40為首次自生物體分離純化所獲得之天然化合物。
上述化合物之化學結構式均是以各種光譜的證據與化學的方法加以確定,吾人並將所獲得的天然化合物進行 P-388、KB、A-549 與 HT-29 四種癌細胞株的細胞毒殺活性測試,測試結果顯示化合物7、32、33、36與37具有中等的細胞毒殺活性。
Abstract
The organic extracts of two marine soft corals Pachyclavularia violacea and Subergorgia suberosa, collected along the coast of Kenting, Taiwan, were found to exhibit significant cytotoxicities toward several cancer cell lines (Table 1). In order to discover bioactive compounds, we have investigated the chemical constituents of these two marine organisms. Investigation on P. violacea has led to the isolation of twenty-five compounds, including twenty-one new compounds, pachyclavulariolide G (1), pachyclavulariolide H (3), pachyclavulariolide I (4), pachyclavulariolides J–S (6–15), pachyclavulariaenones A–G (16–22), secopachyclavulariaenone A (23), and four known compounds pachyclavulariolide (2), pachyclavulariolide E (5), pachyclavulariolide A (24) and pachyclavulariolide B (25).
Also, we have investigated the chemical constituents of S. suberosa. This study led to the isolation of fifteen compounds, including six new compounds, 2b-acetoxysubergorgic acid (27), subergorgiol (31), suberosols A–D (34–37), and nine known compounds, subergorgic acid (26), 2b-hydroxysubergorgic acid (28), methyl ester of subergorgic acid (29), 2b-acetoxy methyl ester of subergorgic acid (30), buddledin D (32), buddledin C (33), 5b-pregnan-3,20-dione (38), Δ1- 5b-pregnen-3,20-dione (39) and 3a-acetoxy -5b-pregnan-20-one (40). Compounds 39, 40 were isolated from natural sources for the first time.
Structures of these compounds were determined on the basis of chemical method and spectroscopic evidences. Cytotoxicities of these compounds against P-388, KB, A-549 and HT-29 cancer cell lines also were described. Compound, 7, 32, 33, 36, 37 have been found to show moderate activity toward the above cancer cell lines.
目次 Table of Contents
中文摘要 1
英文摘要 2

壹、研究動機 6
貳、相關文獻回顧 10
第一節、針對Stolonifera目軟珊瑚之天然物研究 12
第二節、針對Scleraxonia亞目軟珊瑚之天然物研究 44
第三節、文獻回顧之分析 57
參、實驗程序與方 61
第一節、採樣、分離與純化 61
3-1-1:Pachyclavularia violacea部分 61
3-1-2:Subergorgia suberosa部分 62
第二節、利用有機反應進行結構鑑定與衍生物之製備 65
第三節、生物活性之篩檢 65
第四節、使用儀器與材料 67
肆、實驗結果與結構解析 69
第一節、 從軟珊瑚Pachyclavularia violacea所分離之化合物 70
4-1-1. Pachyclavulariolide G (1) 之結構解析 70
4-1-2. Pachyclavulariolide (2) 之結構解析 77
4-1-3. Pachyclavulariolide H (3) 之結構解析 83
4-1-4. Pachyclavulariolide I (4) 之結構解析 89
4-1-5. Pachyclavulariolide E (5) 之結構解析 94
4-1-6. Pachyclavulariolide J (6) 之結構解析 99
4-1-7. Pachyclavulariolide K (7) 之結構解析 104
4-1-8. Pachyclavulariolide L (8) 之結構解析 109
4-1-9. Pachyclavulariolide M (9) 之結構解析 116
4-1-10. Pachyclavulariolide N (10) 之結構解析 121
4-1-11. Pachyclavulariolide O (11) 之結構解析 127
4-1-12. Pachyclavulariolide P (12) 之結構解析 132
4-1-13. Pachyclavulariolide Q (13) 之結構解析 139
4-1-14. Pachyclavulariolide R (14) 之結構解析 143
4-1-15. Pachyclavulariolide S (15) 之結構解析 148
4-1-16. Pachyclavulariaenone A (16) 之結構解析 153
4-1-17. Pachyclavulariaenone B (17) 之結構解析 157
4-1-18. Pachyclavulariaenone C (18) 之結構解析 162
4-1-19. Pachyclavulariaenone D (19) 之結構解析 168
4-1-20. Pachyclavulariaenone E (20) 之結構解析 173
4-1-21. Pachyclavulariaenone F (21) 之結構解析 179
4-1-22. Pachyclavulariaenone G (22) 之結構解析 185
4-1-23. Secopachyclavulariaenone A (23)之結構解析 190
4-1-24. Pachyclavulariolide A (24) 之結構解析 192
4-1-25. Pachyclavulariolide B (25) 之結構解析 201
第二節、 從軟珊瑚P. violacea所獲得之天然化合物之細胞毒殺活性 206
第三節、 從柳珊瑚Subergorgia suberosa分離之天然化合物 207
4-3-1. Subergorgic acid (26) 之結構解析 207
4-3-2. 2b-Acetoxysubergorgic acid (27) 之結構解析 210
4-3-3. 2b-Hydroxysubergorgic acid (28) 之結構解析 215
4-3-4. Methyl ester of subergorgic acid (29) 之結構解析 218
4-3-5. 2b-Acetoxy methyl ester of subergorgic acid (30) 之結構解析 220
4-3-6. Subergorgiol (31) 之結構解析 222
4-3-7. Buddledib D (32) 之結構解析 227
4-3-8. Buddledib D (33) 之結構解析 231
4-3-9. Suberosol A (34) 之結構解析 233
4-3-10. Suberosol B (35) 之結構解析 238
4-3-11. Suberosol C (36) 之結構解析 243
4-3-12. Suberosol D (37) 之結構解析 249
4-3-13. 5b-Prengnan-3,20-dione (38) 之結構解析 249
4-3-14. △1-5b-Prengnen-3,20-dione (39) 之結構解析 254
4-3-15. 3b-Acetoxy-5b-prengnan-20-one (40) 之結構解析 257
第四節、 從柳珊瑚S. suberosa所獲得之天然化合物之細胞毒殺活性 263
伍、結論 264
陸、實驗數據整理 267
柒、參考文獻 281
附錄一、Pachyclavulariolide G (1) 之X-ray實驗數據 291
附錄二、Pachyclavulariolide (2) 之X-ray實驗數據 297
附錄三、Pachyclavulariolide H (3) 之X-ray實驗數據 303
附錄四、Pachyclavulariolide E (5) 之X-ray實驗數據 309
附錄五、Pachyclavulariaenone D (18)之X-ray實驗數據 315
附錄六、Pachyclavulariaenone F (21)之X-ray實驗數據 324
附錄七、Pachyclavulariolide B (25) 之X-ray實驗數據 330
附錄八、Abbreviations 336
附錄九、個人資料暨研究成果目錄 337
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