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博碩士論文 etd-0728104-152606 詳細資訊
Title page for etd-0728104-152606
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
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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
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