論文使用權限 Thesis access permission:校內校外完全公開 unrestricted
開放時間 Available:
校內 Campus: 已公開 available
校外 Off-campus: 已公開 available
論文名稱 Title |
濱海植物花蓮澤蘭之活性倍半萜類環內酯成分研究 Studies on Bioactive Sesquiterpene Lactones From Eupatorium hualienense, Ou, Chung & Peng |
||
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 |
98 |
|
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 |
2004-06-29 |
繳交日期 Date of Submission |
2004-07-28 |
關鍵字 Keywords |
倍半萜類、環內酯、花蓮澤蘭 Eupatorium hualienense, Sesquiterpene Lactones |
||
統計 Statistics |
本論文已被瀏覽 5744 次,被下載 1679 次 The thesis/dissertation has been browsed 5744 times, has been downloaded 1679 times. |
中文摘要 |
含γ內酯之倍半萜類化合物是一種具有生物活性的化合物,而台灣澤蘭在過去的研究中曾經發現過此類化合物。因此以花蓮澤蘭作為研究的材料。台灣東部沿岸採集之花蓮澤蘭 (Eupatorium hualienense C. H. Ou, S. W. Chung & C.-I Peng) 為一台灣特有種植物。於,以甲醇丙酮之混合液萃取後,利用色層分析的方法分離出六個成分,分別為五個新天然化合物,命名為eupahualins A-E(1~5)及一個已知化合物eupasimplicin B(6)。這些化合物的結構鑑定為利用一維及二維核磁共振磁譜、紅外光譜、紫外光譜及質譜等方法完成。 Eupahualin A(1)在C-10上接有一個醛基,C-8接有一個a,b-unsaturated acyl的取代基。Eupahualins B、C(2、3) 在C-10 上同樣接有一個醛基,eupahualin B(2)與eupahualin A(1)之不同處在於eupahualin A(1)之C-4,C-5雙鍵為E-form,而eupahualin B(2)為Z-form。Eupahualin C(3)與eupahualin A(1)之不同處在於eupahualin A(1)的C-4',C-5'依序為CH3與CH2OH,eupahualin C (3)則是相反。Eupahualin D(4)在C-10上接有exocyclic雙鍵,C-1及C-3上分別多了OH基及OAc基的取代。Eupahualin E(5)與eupahualin A(1)之不同處在於在Eupahualin E(5)之C-10上接有酸基。 |
Abstract |
Sesquiterpene lactones contain α,β-unsaturated-γ-lactone as a major structural feature, which in recent studies have been shown to be associ- ated with anti-tumor, cytotoxic, anti-microbial and phytotoxic activities. Previous researchers isolated sesquiterpene lactones from Eupatorium formosanum Hay. Thus, we studied Eupatorium hualienense, a unique speces in Taiwan that grows near the eastern coast. Five new sesquiter- pene lactones of the germacranolide type, eupahualins A-E (1-5) along with the known lactone, eupasimplicin B (6). Their structures were determined by 1D-NMR(1H-NMR,13C-NMR) and 2D-NMR(COSY、NOESY、HMQC、HMBC). Eupahualin A (1) exhibits an aldehyde at C-10 and an a,b-unsatura ted acyl group at C-8. Eupahualin B (2) also has an aldehyde at C-10. The Z-form of C-4, C-5 double bond in eupahualin B (2) is the main difference from the trans-form C-4, C-5 double bond in eupahualin A (1). The difference of eupahualin C (3) and eupahualin A (1) lies in structure of a ester group at C-8. The methyl at C-4' in eupahualin A (1) was changed into hydroxy methyl while the hydroxy methyl of eupahualin A (1) was changed to methyl in eupahualin C (3). Eupahualin D (4) shows exocyclic double bond at C-10, OH at C-1 and OAc at C-3. An carboxylic group (COOH) at C-10 in eupahualin E (5) is the only difference from which in eupahualin A (1). |
目次 Table of Contents |
壹 緒論 7 (一)前言 7 (二)相關研究之文獻回顧 9 (三)研究動機及目標 12 貳 材料與方法 13 (一)材料 13 (二)分離與純化 14 (三)衍生物製備 18 參 結果與討論 19 (一)結構解析 20 一 化合物1, Eupahualin A分子結構之鑑定 20 二 化合物2, Eupahualin B分子結構之鑑定 26 三 化合物3, Eupahualin C分子結構之鑑定 31 四 化合物4, Eupahualin D分子結構之鑑定 34 伍 化合物5, Eupahualin E分子結構之鑑定 39 六 化合物6 , Eupasimplicin B 分子結構之鑑定 42 (二)活性測試 44 (三)討論 45 參考文獻 46 附錄 各成份的光譜資料 48 |
參考文獻 References |
1. (a)Chiaki, K.; Takayoshi, N.; Hiroshi, H.; Kasumim, E.; Takayoshi, T.; Bull. Chem. Soc. Jpn., 1985, 58, 146-151 2. Takahashi, T.; Utagawa, A.; Muraw, T.; Chem. Abstr., 1980, 93, 114734t 3. Woerdenbag, HJ; Pharnaceutisch weekblad scientific edition, 1986, 8, 245-251 4. (a)Hoppe, H.A.; Dogenkunde, B.; Angiospermen, I.; Berlin-New York: Walter de Gruyter, 1975, 482 (b)Van Os FHL, ed. Gids voor geneeskrachtige planten. Amsterdam: The Reader’s Digest NV, 1979, 157 5. Malingre, Th.M.; Pharm weekbld, 1971, 106, 738-744 6. Woerdenbag, H. J., Pharm weekbld scientific edition, 1987, 9, 226 7. Werner Herz, Phytochemistry, 1982, 21, 2475-2478 8. Kupchan, Sharma, R. P., J. Org. Chem., 1969, 34, 3876 9. (a)Mitsumasa; Chem. Pharm. Bull., 1986, 34, 5157(b) Namba,T.; The crude drug in Japan, China and Neighbouring countries.,1980, 32 10. (a) Herz W.; Phytochemistry, 1981, 20, 1343(b)Kupchan; J. Am. Chem. Soc., 1971, 91, 4914-4917 11. Kim, D. K.; Baek, N. I.; Choi, S. U.; Lee, C. O.; Lee, K. R.; Zee, O. P. J Nat Prod., 1997, 60, 1199-1202 12. Hernandez, L. R.; Catalan, C. A. N.; Rojas, C. M. C. G.; Nathan, P. J. Phytochemistry 1996, 42, 1369-1373. 13. Kupchan, J. Org. Chem., 1973, 38, 2189-2192 14. Yang, Y. P.; Liu, H. Y.; Peng, C. I.; Shih, B. L.; Lu, S. Y. in Manual of Taiwan's Vascular Plants, 1999, 5, 255, The Council of Agriculture, The Executive Yuan, Taipei, Taiwan. 15. Gu, G. Q.; Gills, J. J.; Park, E. J.; Mata-Greenwood, E.; Hawthorne, M. E.; Axelrod, F.; Chavez, P. I.; Fong, H. H. S.; Mehta, R. G.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2002, 65, 532-536. 16. (a) Herz. W; Phytochemistry, 1981, 20, 1343(b) Kupchan, J. Org. Chem., 1973, 38, 1260(c) MUPCHAN, S. M.; J.Org Chem, 1973, 38, 1260 17. Yang, Y. P.; Liu, H. Y.; Peng, C. I.; Shih, B. L.; Lu, S. Y. 1999 in Manual of Taiwan's Vascular Plants, Vol. IV, p. 255, The Council of Agriculture, The Executive Yuan, Taipei, Taiwan.Lang, G.; Passreiter, C. M.; Wright, C. W.; Filipowicz, N. H. 18. Abdel Sattar, E.; Galal, A. M.; Mossa, G. S. J. Nat. Prod. 1996, 59, 403-405. 19. Addae-Kyereme, J.; Medinilla, B. E.; Castillo, J. J; Z Naturforsch. 2002, 57, 282-286. 20. Wagner, H.; Jurcic, K. Arzneimittelforschung, 1991, 41, 1072-1076. 21. Herz, W.; Sharma, R. P. J. Org. Chem 1976, 41, 1015-1020. 22. Herz, W.; de Groot, R.; Murari, R.; Blount, J. F. J. Org. Chem 1978, 43, 3559- 3564. |
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:校內校外完全公開 unrestricted 開放時間 Available: 校內 Campus: 已公開 available 校外 Off-campus: 已公開 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 |