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研究生： 李明勳
Ming-Hsun Lee
論文名稱： 電灑游離質譜儀建立魚油及細菌之生化指標
Characterization of fish oil capsules and bacterial by electrospray ionization mass spectrometer
指導教授： 凌永健
Yong-Chien Ling
口試委員:
學位類別： 碩士
Master
系所名稱： 理學院 - 化學系
Department of Chemistry
論文出版年： 2006
畢業學年度： 94
語文別： 中文
論文頁數： 99
中文關鍵詞： 電灑游離質譜儀 、魚油 、三酸甘油酯 、細菌 、磁性奈米粒子 、萬古黴素
外文關鍵詞： electrospray ionization mass spectrometer, fish oil, triglyceride, bacterial, magnetic nanoparticle, Vancomycin
相關次數： 點閱：3  下載：0 
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    • 本研究乃針對魚油及細菌分析，利用電灑游離質譜儀建立各自的生化指標，期望開發一快速分析且準確的方法。子題分別為：（一）直接注入電灑游離質譜儀建立魚油生化指標；（二）液相層析電灑游離質譜儀搭配磁性濃縮奈米粒子偵測食品中毒病原菌。
    研究子題一為將魚油膠囊經由簡單的前處理，並且利用減去層析分離的直接注入法來上機偵測，期望達到快速分析的目標。而在儀器偵測方面，僅藉由電灑游離質譜儀及串連式質譜儀的分析，再搭配上獨特的三酸甘油酯組成表，計算分析出魚油膠囊的種類。結果顯示，首先透過此分析方法可將真實魚油分為兩大類，含有較高濃度多元不飽和脂肪酸的魚種及含有較低濃度多元不飽和脂肪酸的魚種。而進一步應用到魚油膠囊及鯊魚肝油膠囊的測試，則發現到魚油膠囊皆含有多元不飽和脂肪酸所組成的三酸甘油酯，鯊魚肝油則由於內容物與魚油相異，因此並無明顯訊號，但其中兩個鯊魚肝油膠囊樣品則發現含有與前者油脂截然不同的訊號，表示有摻入其他油脂。
    研究子題二中由於為了達到快速分析的目標，因此製備了僅針對革蘭氏陽性菌具有鍵結力的磁性奈米粒子，將於前處理中與細菌鍵結，再藉由磁力吸引與其他基質分離，達到濃縮的效果。之後再以細菌蛋白質作為指標，透過液相層析電灑游離質譜儀的分析，將結果與網路資料庫做一比對，不僅得到各細菌所含有的蛋白質分子量，又增加各蛋白質於液相層析的滯留時間作為另一鑑定的證據。

    This thesis consists of two projects: (1) characterization of fish oil capsules using triglyceride (TG) as biological marker by direct injection electrospray ionization mass spectrometer (ESI-MS); (2) classification of bacterial causing food poison by magnetic nanoparticles concentration and liquid chromatography (LC) ESI-MS detection.
    The first project uses simple pretreatment coupled with direct injection to rapidly analyze fish oil capsules by sparing liquid chromatography. Furthermore, ESI-MS/MS was also exploited to characterize TG. A comprehensive TG list was established and used to infer the TG structure successfully. The method was successfully used to classify real fish oil capsules samples, which were consisted of two categories. One contains high concentration polyunsaturated fatty acid (PUFA) and the other contains low concentration PUFA. However, the three shark liver oil samples were failed to be detected by ESI-MS. Two of the three displayed unusual mass spectra and were presumably being adulterated.
    The second project pertains to rapidly detect bacterial. The Vancomycin-coupled magnetic nanoparticles which interact with Gram-positive bacterial only were prepared and used to concentrate bacterial from matrix. The concentrated bacterial were classified using protein as biological marker by LC ESI-MS. The dual results of molecular mass and retention time of proteins are advantageous to ubiquitous identification of bacterial.

    目錄 第一章 緒論 1 1.1 研究動機及實驗目標 1 1.2 儀器簡介 3 1.2.1 電灑游離法 3 1.2.2 質量分析器及串連式質譜儀 4 1.2.3 液相層析電灑游離質譜儀 4 1.3 參考文獻 5 第二章 直接注入電灑游離質譜儀建立魚油生化指標 8 2.1 前言 8 2.1.1 魚油簡介 8 2.1.2 魚油主要組成 10 2.1.3 分析油脂方法回顧 11 2.2 實驗方法 13 2.2.1 試藥 13 2.2.2 真實魚油樣品及膠囊樣品 13 2.2.3 實驗設備 13 2.2.4 實驗步驟 14 2.2.5 直接注入電灑游離質譜儀分析條件 15 2.3 結果與討論 16 2.3.1 分析三酸甘油酯的組成 16 2.3.2 真實魚油的分析 18 2.3.3 魚油膠囊的分析 22 2.4 結論 26 2.5 參考文獻 27 第三章 液相層析電灑游離質譜儀搭配磁性濃縮奈米粒子偵測食品中毒病原菌 54 3.1 前言 54 3.1.1 食品中毒細菌之檢驗方法 55 3.1.2 液相層析電灑式質譜儀分析細菌 59 3.1.3 磁性奈米粒子之應用 61 3.2 實驗方法 64 3.2.1 試藥 64 3.2.2 實驗設備 64 3.2.3 細菌樣品 65 3.2.4 細菌蛋白質萃取及分析 66 3.2.5 蛋白質資料庫搜尋 67 3.2.6 磁性奈米粒子之製備及修飾 67 3.2.7 磁性奈米粒子性質分析 68 3.2.8 磁性濃縮奈米粒子濃縮細菌 69 3.3 結果與討論 70 3.3.1 細菌樣品偵測 70 3.3.2 磁性濃縮奈米粒子之性質 72 3.3.3 磁性濃縮奈米粒子應用於細菌偵測 74 3.4 結論 77 3.5 參考文獻 78 表目錄 表2-1 八大類油脂。 31 表2-2 常見的脂肪酸。 32 表2-3 三酸甘油酯組成表（擷取），以分子量858為例。 33 表2-4 真實魚種的主要三酸甘油酯組成。 34 表2-5 魚體油的主要三酸甘油酯組成。 35 表2-6 疑似摻假之鯊魚肝油的主要三酸甘油酯組成。 36 表3-1 中華民國九十一年至九十三年，台灣地區食品中毒事件統計。 82 表3-2 中國國家標準「食品微生物之仙人掌桿菌之檢驗」。 83 表3-3 細菌之各生化指標比較。 84 表3-4 金黃色葡萄球菌及仙人掌桿菌之O.D.600實驗結果。 85 表3-5 金黃色葡萄球菌蛋白質訊號列表。 86 表3-6 仙人掌桿菌蛋白質訊號列表。 87 表3-7 腸炎弧菌蛋白質訊號列表。 88 表3-8 大腸桿菌蛋白質訊號列表。 89 表3-9 經由磁性奈米粒子濃縮後的金黃色葡萄球菌蛋白質訊號列表。 90 表3-10 經由磁性奈米粒子濃縮後的仙人掌桿菌蛋白質訊號列表。 91 圖目錄 圖1-1 電灑游離質譜儀之基本結構。 6 圖1-2 電灑游離源之基本結構。 7 圖2-1 (a)DHA，(b)EPA，(c)鯊烯。 37 圖2-2 Omega-3脂肪酸於自然界的形成路徑。 38 圖2-3 人體體內膽固醇形成路徑。 39 圖2-4 脂肪酸結構式。(a)硬脂酸（stearic acid），(b)油酸（oleic acid）。 40 圖2-5 標準樣品之直接注入電灑游離質譜圖。(a) SOO (C18:0/C18:1 /C18:1)，(b) SOS (C18:0/C18:1/ C18:0)。 41 圖2-6 二酸甘油酯之可能掉失形成路徑。(a)SOO，(b)SOS。 42 圖2-7 標準樣品。(a) SOO，m/z 904.7的子離子質譜圖，(b) SOS，m/z 906.7的子離子質譜圖。 43 圖2-8 真實魚油之直接注入電灑游離質譜圖。(a)圓鱈，(b)扁鱈，(c)鮭魚，(d)鯖魚。 44 圖2-9 真實魚油之直接注入電灑游離質譜圖於m/z 750~1050三酸甘油酯訊號峰放大圖，粗框標記為不含有多元不飽和脂肪酸的三酸甘油酯訊號峰群，底線粗斜體標記為含有多元不飽和脂肪酸的三酸肝油脂訊號峰群。(a)圓鱈，(b)扁鱈，(c)鮭魚，(d)鯖魚。 45 圖2-10 圓鱈魚油。(a) m/z 876.6之子離子質譜圖，(b)m/z 902.6之子離子質譜圖，(c)m/z 930.6之子離子質譜圖，(d)m/z 958.6之子離子質譜圖。 46 圖2-11 扁鱈魚油。(a)m/z 930.6之子離子質譜圖， (b) m/z 932.6之子離子質譜圖。 47 圖2-12 鮭魚油。(a)m/z 896.6之子離子質譜圖，(b)m/z 922.6之子離子質譜圖。 48 圖2-13 魚體油膠囊之直接注入電灑游離質譜圖。(a)F1，(b)F2，(c)F3。 49 圖2-14 魚體油膠囊之直接注入電灑游離質譜圖於m/z 750~1050三酸甘油酯訊號峰放大圖。粗框標記為不含有多元不飽和脂肪酸的三酸甘油酯訊號峰群，底線粗斜體標記為含有多元不飽和脂肪酸的三酸肝油脂訊號峰群，粗體粗框標記為含有兩個多元不飽和脂肪酸的三酸甘油酯訊號峰。(a)F1，(b)F2，(c)F3。 50 圖2-15 魚體油膠囊F1。(a)m/z之子離子質譜圖，(b)m/z 942.6之子離子質譜圖，(c)m/z 968.6之子離子質譜圖。 51 圖2-16 鯊魚肝油膠囊之直接注入電灑游離質譜圖。(a)S2，(b)S3，(c)S4，(d)S6，(e)S7，(f)S8。 52 圖2-17 疑似摻假鯊魚肝油膠囊之直接注入電灑游離質譜圖。(a)S1，(b)S5，(c)S1之 m/z 750~1050區域放大圖，(d)S5之m/z 750~1050區域放大圖。 53 圖3-1 檢測病患遭受微生物感染之流程圖。 92 圖3-2 液相層析電灑游離質譜儀分析細菌蛋白質之層析圖。(a)金黃色葡萄球菌，(b)仙人掌桿菌，(c)腸炎弧菌，(d)大腸桿菌。 93 圖3-3 磁性奈米粒子之TEM圖，使用Lacey carbon銅網。 94 圖3-4 IR光譜圖。(a)萬古黴素，(b)未修飾的磁性奈米粒子，(c)修飾上萬古黴素之磁性濃縮奈米粒子。 95 圖3-5 TGA結果圖，黑線為未修飾的磁性奈米粒子，虛線為修飾上萬古黴素之磁性濃縮奈米粒子，粗線為萬古黴素。 96 圖3-6 萬古黴素殺菌機制圖。 97 圖3-7 經磁性奈米粒子濃縮後上清液之UV/Vis光譜圖，實線為加入磁性奈米粒子濃縮前，虛線為加入磁性奈米粒子濃縮後。(a)金黃色葡萄球菌，(b)仙人掌桿菌，(c)腸炎弧菌，(d)大腸桿菌。 98 圖3-8 利用磁性濃縮奈米粒子實際測試菌液之液相層析電灑游離質譜儀層析圖。(a)金黃色葡萄球菌，(b)仙人掌桿菌。 99

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