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研究生:詹益福
研究生(外文):Yi-Fu Chan
論文名稱:臺灣扁柏葉部之成分研究
論文名稱(外文):Studies on the Constituents of the Leaves of Chamaecyparis obtusa var. formosana
指導教授:郭悅雄郭悅雄引用關係
指導教授(外文):Yueh-Hsiung Kuo
學位類別:博士
校院名稱:國立臺灣大學
系所名稱:化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2004
畢業學年度:92
語文別:中文
論文頁數:310
中文關鍵詞:葉部臺灣扁柏
外文關鍵詞:LeavesChamaecyparis obtusa var. formosana
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台灣扁柏(Chamaecyparis obtusa var. formosana),又名黃檜或厚殼,特產於台灣中央山脈海拔1,300~2,800公尺之山區,其木材有辣味、具芳香、且耐朽抗蟲性之強,本省其他木材均難與之匹敵。台灣扁柏葉部,以丙酮浸泡得到之萃取物。運用矽膠薄層分析、高效液相層析儀及再結晶等方法進行進一步的分離純化。單離以後的化合物在測得紅外線光譜、氫核磁共振圖譜、碳核磁共振圖譜與質譜後,經推測為已知化合物者,則與文獻值比對確定其結構。若是新化合物,依需要進行二維核磁共振圖譜實驗確定其結構。

本實驗共鑑定得到120個化合物,分別為:
一、倍半萜類(Sesquiterpenoids) 化合物 21個
二、雙萜類(Diterpenoids) 化合物63個
三、木酚素類(Lignoids) 化合物19個
四、固醇類(Steroids) 化合物2個
五、其他類(Others) 化合物15個

其中21個為新化合物,3個為從天然界首次分離得到的化合物,新化合物中有1個具有新骨架。分析台灣扁柏葉部的化學成分,發現其化合物骨架及立體關係變化多端且極為有趣。
Chamaecyparis obtusa var. formosana (Cupressacece) is endemic to Taiwan, distributed at altitudes of 1,300~2,800 meters. The wood of this tree is the best building materials in Taiwan.
The acetone extract from the leaves of C. obtusa var. formosana was concentrated to give a residue which was partitioned between ethyl acetate and water. The ethyl acetate layer was separated by column chromatography on silica gel, preparative thin layer chromatography and high performance liquid chromatography (HPLC) to give 120 compounds. Of these compounds, 21 of them are new (including one novel skeleton) and 3 are isolated for the first time from natural sources. Among the isolated components, there are 21 sesquiterpenoids, 63 diterpenoids, 19 lignoids, 2 steroids, the other 15 do not belong to any of the above categories.
The known compounds were identified by spectral analysis and compared with those reported in literatures or from authentic samples. The structures of new compounds were elucidated by spectral evidence including 1D and 2D techniques.
中文摘要-----------------------------------------------------------------------------------I
英文摘要-----------------------------------------------------------------------------------II

一、緒論
第一節:緒言----------------------------------------------------------------1
第二節:台灣扁柏植物簡介----------------------------------------------1
第三節:扁柏屬植物之研究概述----------------------------------------2

二、結果與討論
化合物分離表----------------------------------------------------------------29
第一節:萃取與分離-------------------------------------------------------30
第二節:倍半萜類化合物結構鑑定
化合物S21結構鑑定-----------------------------------------------------47
第三節:雙萜類化合物結構鑑定
化合物D12結構鑑定----------------------------------------------------57
化合物D14結構鑑定----------------------------------------------------66
化合物D15結構鑑定----------------------------------------------------71
化合物D16結構鑑定----------------------------------------------------78
化合物D17結構鑑定----------------------------------------------------85
化合物D22結構決定----------------------------------------------------92
化合物D23結構鑑定----------------------------------------------------99
化合物D26結構鑑定---------------------------------------------------106
化合物D40結構鑑定---------------------------------------------------113
化合物D51結構鑑定---------------------------------------------------119
化合物D52結構鑑定---------------------------------------------------128
化合物D54結構鑑定---------------------------------------------------136
化合物D55結構鑑定---------------------------------------------------144
化合物D56結構鑑定---------------------------------------------------152
化合物D57結構鑑定---------------------------------------------------159
化合物D58結構鑑定---------------------------------------------------166
化合物D59結構鑑定---------------------------------------------------175
化合物D60結構鑑定---------------------------------------------------180
化合物D61結構鑑定---------------------------------------------------190
化合物D62結構鑑定---------------------------------------------------200
第四節:木酚素類化合物結構鑑定
化合物L11結構鑑定---------------------------------------------------210
化合物L12結構鑑定---------------------------------------------------217
第五節:其他類化合物結構鑑定
化合物OT16結構鑑定-------------------------------------------------225

三、結論--------------------------------------------------------------------------------235

四、實驗部份
4-1: 儀器與藥品----------------------------------------------------------241
4-2: 實驗步驟-------------------------------------------------------------242
4-3: 化合物數據----------------------------------------------------------247

五、參考文獻-------------------------------------------------------------------------302









表次

表I 過去文獻所報導之扁柏屬(Chamaecyparis genus)植物成分---------------3
表II 粗分離物之活性測試結果----------------------------------------------------237
表III 純化合物之KB Cells活性測試----------------------------------------------238
表IV 粗分重量分配狀況--------------------------------------------------------------242
表V 台灣扁柏葉部乙酸乙酯層部份分離出成分重量-------------------------244
表VI 本實驗中以HPLC純化之部份分離條件----------------------------------245
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