論文使用權限 Thesis access permission:校內一年後公開,校外永不公開 campus withheld
開放時間 Available:
校內 Campus: 已公開 available
校外 Off-campus:永不公開 not available
論文名稱 Title |
台灣產海綿Ircinia formosana天然物研究 Studies on the Natural Products from the Taiwanese Sponge Ircinia formosana |
||
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 |
102 |
|
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 |
2007-07-20 |
繳交日期 Date of Submission |
2007-08-10 |
關鍵字 Keywords |
海綿、天然物 Ircinia formosana, Sponge |
||
統計 Statistics |
本論文已被瀏覽 5692 次,被下載 11 次 The thesis/dissertation has been browsed 5692 times, has been downloaded 11 times. |
中文摘要 |
本論文主要研究台灣產海綿Ircinia formosana之甲醇/二氯甲烷之萃取物,以矽膠管柱層析和高壓液態層析儀純化後,分離出八個化合物,皆屬於linear C-22-sesterterpenoid骨架,其中包含六個新的天然物,將其命名為irciformonins E~J (1~6),與兩個已知化合物,經比對文獻後得知為irciformonins A和B。 所有化合物的結構解析是利用ㄧ維及二維核磁共振圖譜(1D-NMR and 2D-NMR)、旋光(optical rotation)、紅外光光譜(IR)、紫外光光譜(UV)及高解析質譜(high resolution mass spectrum)和比對相關文獻來鑑定。立體結構的判定則是以MM2、NOESY圖譜和比對相關文獻來判定的。 所有化合物主要的構造有一個furan環、五元環內酯和三組甲基訊號。化合物1和2是幾何學上的同分異構物,僅甲氧基的取代與一組雙鍵位置不同,甲氧基的取代分別位於C-10和C-12位上,雙鍵則分別位於C-11/C-12和C-10/C-11上。化合物3和6在結構上只差羥基的取代與一組雙鍵位置不同,化合物3在C-12位上多了一個羥基的取代,化合物3與6的雙鍵則分別位於C-10/C-11和C-11/C-12上。化合物4於C-12~C-15位上為一五元環結構,C-10位上則氧化成酮基。¬而化合物5於C-10、C-15位上有兩個乙醯基的取代。 |
Abstract |
Six new compounds, irciformonins E~J (1~6), were isolated from CH2Cl2/MeOH extract of the sponge Ircinia formosana collected in Taiwan, toghther with two known compounds, irciformonins A and B. These compounds possess a linear C-22-sesterterpenoids type skeleton. The structures of all compounds were elucidated by spectroscopic analysis including 1D and 2D-NMR, optical rotation, IR, UV and high resolution mass spectra, as well as comparison with those in references. The stereochemistry of these compounds were determined by NOESY experiments, MM2 minimized energy, as well as comparison with those in references. The structures of all compounds possess a furan ring, a five membered lactone ring , and three methyl groups. Compounds 1 and 2 are geometric isomers. The differences between them are the substituents of the methoxyl group and the double bond. Compounds 1 and 2 possess substituents of the methoxyl group at C-10 and C-12 and have the double bond at C-11/C-12 and C-10/C-11. The differences between compounds 3 and 6 are the functional groups of the acetyl moeity and the double bond. Compound 3 has an acetyl group at C-12. Compounds 3 and 6 contain two double bonds at C-10/C-11 and C-11/C-12. Compound 4 has a cyclopentane between C-12~C-15 and a ketone group at C-10 while compound 5 possesses two acetyl groups at C-10 and C-15 positions. |
目次 Table of Contents |
壹、 緒論 ㄧ、前言 1 二、文獻回顧 3 三、研究動機 17 貳、 材料與方法 ㄧ、樣品採集 18 二、分離流程 19 三、化學結構鑑定26 參、 實驗結果 ㄧ、化合物結構解析 28 1. Irciformonin E (1)之化學結構解析 28 2. Irciformonin F (2)之化學結構解析 38 3. Irciformonin G (3)之化學結構解析 47 4. Irciformonin H (4)之化學結構解析 56 5. Irciformonin I (5)之化學結構解析 65 6. Irciformonin J (6)之化學結構解析 74 肆、結論 82 伍、參考文獻 86 陸、附錄 ㄧ、化合物1之八種MM2最低能量模型排列 88 二、化合物1~6之物理資料 92 |
參考文獻 References |
1.分析測試學報, 2006, 25, 133-138 2. G. J. Aune, T. Furuta. Y. Pommier, Anticancer Drugs, 2002, 13, 545-555 3. M. Suffness, D. J. Newman, K. M. Sander, Bioorg. Mar. Chem. 1989, 3, 131-167 4. G. Cimino, S. De Stefano and L. Minale, Tetrahedron, 1972, 28, 333-341 5. G. Cimino, S. De Stefano and L. Minale, Tetrahedron, 1972, 28, 1315-1324 6. G. Cimino, S. De Stefano and L. Minale, Tetrahedron, 1972, 28, 5983-5991 7. F. Cafieri, E. Fattorusso, C. Santacroce and L. Minale, Tetrahedron, 1972, 28, 1579-1583 8. D. J. Faulkner, Tetrahedron Lett., 1973, 14, 3821-3822 9. I. Rothberg and P. Shubiak, Tetrahedron Lett., 1975, 10, 769-772 10. A. G. Gonzalez, M. L. Rodriguez and A. S. M. Barrientos, J. Nat. Prod., 1983, 46, 256-261 11. L. V. Manes, P. Crews,M. B. Ksebati and F. J. Schmitz, J. Nat. Prod., 1986, 49, 787-793 12. C. J. Barrow, J. W. Blunt, M. H. G. Munro and N. B. Perry, J. Nat. Prod., 1988, 51, 1294-1298 13. M. O. Garcia, A. D. Rodriguez, Tetrahedron, 1990, 46, 1119-1124 14. A. De Giulio, S. De Rosa, G. Di Vincenzo and G. Strazzullo, J. Nat. Prod., 1990, 53, 1503-1507 15. A. Martinez, C. Dunque, N. Hara and Y. Fujimoto, Nat. Prod. Lett., 1995, 6, 281-284 16. G. Bifulco, I. Bruno, L. Minale, R. Riccio, C. Debitus, G. Bourdy, A. Vassas and J. Lavayre, J. Nat. Prod., 1995, 58, 1444-1449 17. S. De Rosa, A.Milone, A. De Giulio, A. Crispino and C. Iodice, Nat. Prod. Lett., 1996, 8, 245-251 18. A. Martinez, C. Duque, N. Sato, Y. Fujimoto, Chem. Pharm. Bull., 1997, 45, 181-184 19. M. S. Buchanan, A. Edser, G. King, J. Whitmore , J. R. Quinn, J. Nat. Prod., 2001, 64, 300-303 20. Y. Murakami, M. Takei, K. Shindo, C. Kitazume, J. Tanaka, T. Higa, H. Fukamachi, J. Nat. Prod., 2002, 65, 259-261 21. H. H. Issa, J. Tanaka and T. Higa, J. Nat. Prod., 2003, 66, 251-254 22. G. R. Pettit, J.-P. Xu , J.-C. Chapuis, R. K. Pettit, L. P. Tackett, D. L. Doubek, J. N. A. Hooper, J. M. Schmidt, J. Med. Chem., 2004, 47, 1149-1152 23. Y.-C. Shen, K.-L. Lo, Y.-C. Lin, A. T. Khalil, Y.-H. Kuo and P.-S. Shih, Tetrahedron Lett., 2006, 47, 4007-4010 |
電子全文 Fulltext |
本電子全文僅授權使用者為學術研究之目的,進行個人非營利性質之檢索、閱讀、列印。請遵守中華民國著作權法之相關規定,切勿任意重製、散佈、改作、轉貼、播送,以免觸法。 論文使用權限 Thesis access permission:校內一年後公開,校外永不公開 campus withheld 開放時間 Available: 校內 Campus: 已公開 available 校外 Off-campus:永不公開 not available 您的 IP(校外) 位址是 18.207.163.25 論文開放下載的時間是 校外不公開 Your IP address is 18.207.163.25 This thesis will be available to you on Indicate off-campus access is not available. |
紙本論文 Printed copies |
紙本論文的公開資訊在102學年度以後相對較為完整。如果需要查詢101學年度以前的紙本論文公開資訊,請聯繫圖資處紙本論文服務櫃台。如有不便之處敬請見諒。 開放時間 available 已公開 available |
QR Code |