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研究生: 張琨閔
Chang, Kun-min
論文名稱: 輔酶CoQ10衍生物之合成與活性分析
Synthesis and Activity Analysis of Coenzyme Q10 Derivatives
指導教授: 蕭世裕
Shaw, Shyh-yu
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系碩士在職專班
Department of Chemistry (on the job class)
論文出版年: 2008
畢業學年度: 96
語文別: 中文
論文頁數: 85
中文關鍵詞: 輔酶
外文關鍵詞: CoQ10
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  • 近年來輔酶CoQ10被應用在生化、醫藥、食品、化妝品領域中。當CoQ10被還原後形成Ubiquinol-10則容易被氧化,本研究主要針對Ubiquinol-10上的氫氧根官能基做衍生化反應得到CoQ10的衍生物,並測試CoQ10與其衍生物的活性比較。
    以氫氧根官能基做酯化反應為主,合成出acetylated CoQ10(ACoQ10)、octanoylated CoQ10(OCoQ10)、succinylated CoQ10(SCoQ10)、semi- succinylated CoQ10(semi-SCoQ10)以及phosphate CoQ10(PCoQ10),其中ACoQ10、OCoQ10酯化反應是在鹼性條件進行,Ubiquinol-10與具有醯氯官能基反應,在室溫下反應時間只需30分鐘,得到的衍生物產率達95%以上,顯示以此方式進行酯化反應速率快、產率高。另外將CoQ10改變官能基後,發現其中SCoQ10、semi-SCoQ10、PCoQ10可以溶在醇類溶劑中,顯示衍生化的結果成功的將脂溶性的CoQ10,轉變具有親水性的結構。
    每個衍生物除了可以保存在室溫中,經細胞抗氧化活性測試發現,semi-SCoQ10與PCoQ10的生物抗氧化能力比CoQ10好。

    Coenzyme Q10 has been widely used in biochemistry recent years, including pharmaceutical﹑food and cosmetic fields. Ubiquinol-10 is the reduced form of CoQ10 which is easily oxidizied to CoQ10. The main purpose of the research is to prepare the derivatives of Ubiquinol-10 and examine their anti-oxidation activities.
    A series of esterification modification has been performed on Ubiquinol-10 including acetylated CoQ10 (ACoQ10)﹑octanoylated CoQ10 (OCoQ10)﹑succinylated CoQ10 (SCoQ10)﹑semi-succinylated CoQ10 (semi-SCoQ10) and phosphate CoQ10 (PCoQ10). Esterification reactions of acetylated CoQ10 and octanoylated CoQ10 can be achieved under alkali condition. A milder esterification condition has been developed on the ubiquinol-10 by acetyl chloride reagents, the reaction can be achieved within 30 minutes and above 95% yield. It's a feasible method to produce ester derivatives at high reaction rate and yield.
    In terms of the solubility of ubiquinol-10 modified compounds, the SCoQ10﹑semi-SCoQ10 and PCoQ10 can be dissolved in alcohol solvents, it means the derivatization results changed the hydrophobic CoQ10 to become more hydrophilic property.
    Every derivatives are stable at room temperature and can be stored easily. Among the derivatives, the anti-oxidation activity of semi-SCoQ10﹑PCoQ10 are better than the others.

    中文摘要------------------------------------------------Ⅰ 英文摘要------------------------------------------------Ⅱ 目錄----------------------------------------------------Ⅳ 表目錄--------------------------------------------------Ⅶ 圖目錄--------------------------------------------------Ⅷ CoQ10及其衍生物之簡稱、化學名、分子式及結構對照圖-----ⅩⅡ 第一章 緒論----------------------------------------1 1.1 Coenzyme Q10的發現--------------------------1 1.2 Coenzyme Q10的結構--------------------------1 1.3 Coenzyme Q10的合成--------------------------2 1.4 Coenzyme Q10的功能--------------------------4 1.5 Coenzyme Q10的應用--------------------------5 1.6 Coenzyme Q10衍生物的介紹--------------------6 1.7 研究目的------------------------------------8 1.8 合成策略------------------------------------8 第二章 實驗步驟與材料---------------------------- 10 2.1 實驗藥品--------------------------------------- 10 2.2 儀器------------------------------------------- 12 2.3 實驗步驟--------------------------------------- 13 2.3.1 Ubiquinol-10合成步驟------------------------13 2.3.2 ACoQ10合成步驟------------------------------13 2.3.3 OCoQ10合成步驟------------------------------14 2.3.4 SCoQ10與semi-SCoQ10合成步驟-----------------14 2.3.5 PCoQ10合成步驟----------------------------- 15 2.4 實驗分析--------------------------------------- 15 2.4.1 UV分析--------------------------------------15 2.4.2 FT-IR分析-----------------------------------16 2.4.3 薄層層析分析------------------------------- 16 2.4.4 HPLC分析------------------------------------16 2.4.5 NMR分析-------------------------------------17 2.4.6 MS分析--------------------------------------17 2.4.7 溶解度測試--------------------------------- 17 2.4.8 CoQ10衍生物之細胞抗氧化分析---------------- 17 2.4.9 CoQ10衍生物之安定性測試-------------------- 18 第三章 結果與討論-------------------------------- 19 3.1 Ubiquinol-10的合成------------------------------19 3.2 ACoQ10的合成------------------------------------19 3.3 OCoQ10的合成------------------------------------21 3.4 SCoQ10與semi-SCoQ10的合成-----------------------23 3.5 PCoQ10的合成------------------------------------26 3.6 UV分析結果--------------------------------------27 3.7 FT-IR分析結果-----------------------------------28 3.8 TLC分析結果-------------------------------------28 3.9 HPLC分析結果------------------------------------29 3.10 CoQ10衍生物溶解度比較------------------------- 30 3.11 CoQ10衍生物產率比較--------------------------- 32 3.12 CoQ10衍生物之細胞抗氧化分析結果--------------- 32 3.13 CoQ10衍生物之安定性測試結果------------------- 34 第四章 結論-------------------------------------- 36 第五章 參考文獻---------------------------------- 39

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