輔仁大學學術資源網

記錄編號	6553
狀態	NC094FJU00255005
助教查核
索書號
學校名稱	輔仁大學
系所名稱	食品營養學系
舊系所名稱
學號	492446062
研究生(中)	李憲韋
研究生(英)	Hsien-Wei Lee
論文名稱(中)	滷味食品中膽固醇氧化物之形成與抑制
論文名稱(英)	Formation and Inhibition of Cholesterol Oxidation Products in Marinated Foods
其他題名
指導教授(中)	陳炳輝
指導教授(英)	Bing-Huei Chen
校內全文開放日期	不公開
校外全文開放日期	不公開
全文不開放理由
電子全文送交國圖.	同意
國圖全文開放日期.	2006.02.03
檔案說明	電子全文
電子全文	01
學位類別	碩士
畢業學年度	94
出版年
語文別	中文
關鍵字(中)	膽固醇氧化物滷味食品
關鍵字(英)	cholesterol oxidation products (COPs) marinated foods
摘要(中)	許多研究顯示膽固醇氧化產物（cholesterol oxidation products，COPs）會對人體健康造成傷害。含高量膽固醇的滷味食品，例如滷肉和滷蛋，容易經長時間加熱而生成大量的COPs。本研究目的為以氣相層析-質譜儀分析滷肉、滷蛋與滷汁中的COPs，比較加熱時間、滷汁成分醬油和冰糖的添加量與抗氧化劑對滷味食品中COPs生成或抑制的影響。結果顯示，滷蛋的COPs含量明顯高於滷肉，長時間加熱均會導致滷蛋及滷肉中COPs含量顯著增加。滷肉之COPs含量於加熱期間的增加趨勢較滷蛋顯著，於24小時加熱後增加83 %以上。滷汁中添加醬油及冰糖皆具有抑制膽固醇氧化的效果，在滷蛋及滷肉中以冰糖的效果較佳，滷汁則以添加10 %醬油的效果最好。另外，抗氧化劑如維生素C、維生素E、BHA及Trolox的添加均具有抑制COPs生成的能力，其中以維生素C對滷蛋的膽固醇氧化抑制效果最佳，滷肉及滷汁中則以添加BHA的效果較好。BHA及Trolox於大部分條件下均會隨添加量的增加而具有更好的抑制效果，但維生素E於低濃度的效果較佳，維生素C對滷蛋中膽固醇氧化的抑制效果則是以添加高濃度者較佳，但滷肉及滷汁中的抑制效果則是以添加低濃度者較佳。
摘要(英)	Many studies have shown that cholesterol oxidation products (COPs) may be detrimental to human health. Marinated foods rich in cholesterol, such as egg and meat, may be susceptible to formation of high amount of COPs after prolonged heating. The objectives of this study were to analyze the COPs content in marinated meat, egg and juice by GC-MS, as well as compare the effect of heating time, level of soy sauce and crystal sugar in marinated juice, and antioxidants on the formation or inhibition of COPs. Results showed that the COPs were formed at a higher level in marinated egg than in marinated meat. During extensive heating, a pronounced increase of COPs was observed in both marinated egg and meat, however, a larger increase was found for the latter when compared to the former. After heating for 24 h, the amount of COPs in marinated meat increased more than 83 %. The incorporation of soy sauce and crystal sugar was effective in inhibiting COPs formation; the former was more efficient in marinated juice, while the latter was efficient in marinated egg and meat. In addition, the addition of antioxidants such as vitamin C, vitamin E, BHA and Trolox were also effective in inhibiting COPs formation. The best protective effect was shown for vitamin C in marinated egg, BHA in marinated meat and marinated juice. The inhibition effect increased both with increasing concentration of BHA and Trolox. Unlike BHA and Trolox, a better inhibition effect was found for vitamin E at a low concentration. However, a better inhibition effect was shown for vitamin C at a high concentration in marinated egg, and a reversed trend occurred in marinated meat and juice.
論文目次	目錄頁次第一章緒言…………………………………………………………1 第二章文獻回顧……………………………………………………3 一、膽固醇簡介………………………………………………………3 二、膽固醇氧化產物簡介……………………………………………5 三、膽固醇氧化產物的生理影響……………………………………7 （一）心血管疾病………………………………………………….7 （二）抑制酵素活性……………………………………………….7 （三）細胞毒性…………………………………………………….8 （四）致突變性與致癌性…………………………………………11 四、膽固醇氧化機制………………………………………………..11 （一）自氧化反應…………………………………………………13 （二）光氧化反應…………………………………………………18 五、影響膽固醇氧化的因子………………………………………..18 （一）食品組成分…………………………………………………18 （二）熱處理………………………………………………………22 （三）抗氧化劑……………………………………………………27 （四）酸鹼值………………………………………………………35 六、膽固醇氧化物的萃取、定性與定量分析……………………..38 （一）分離及純化…………………………………………………38 （二）定量及定性分析……………………………………………41 七、滷味食品………………………………………………………..47 第三章材料與方法…………………………………….…………54 一、研究架構………………………………………….………….54 （一）不同滷煮時間對滷肉、滷蛋及滷汁COPs生成的影響…………………………………………….……...54 （二）不同滷汁成分對COPs生成的影響………….……….55 （三）添加抗氧化劑對滷肉、滷蛋及滷汁COPs生成的影響………………………………….………………...56 二、試驗材料………………………………….………………….57 （一）原料…………………………………….………………57 （二）試藥暨材料………………………….…………………57 三、儀器設備…………………………………………….……….59 （一）分析COPs設備－氣相層析質譜儀………….……….59 （二）分析殘留抗氧化劑設備－高效率液相層析（HPLC）……………………………………….…….60 （三）COPs萃取純化設備……………………………….…..60 （四）其他設備………………………………………….……62 四、實驗方法……………………………………………….…….62 （一）氣相層析質譜儀（GC / MS）分析COPs…...….……62 （二）滷味中COPs之萃取純化……………………….….…63 （三）COPs的分析…………………………………….….….64 （四）滷煮時間對滷肉、滷蛋及滷汁COPs生成的影響..…66 （五）滷汁成分對COPs生成的影響……………………..…67 （六）添加抗氧化劑對滷肉、滷蛋及滷汁COPs生成的影響………………………………………………….…67 （七）市售滷肉中COPs含量分析……………….………….68 （八）滷味中殘留胺基態氮分析………………….…………68 （九）滷味中還原糖含量分析…………………….…………69 （十）滷味中殘留抗氧化劑分析………………….….………72 （十一）統計分析………………………………….….………74 第四章結果與討論…………………………………….……….…75 一、標準品的選擇及分析條件的確立……………….…………..75 二、滷味中COPs之萃取與純化……………………….………...88 三、標準曲線…………………………………………….………..98 四、偵測極限…………………………………………….………..98 五、加熱時間對滷蛋、滷肉及滷汁COPs生成的影響….….….103 （一）加熱時間對滷蛋中COPs生成的影響……….…….....105 （二）加熱時間對滷肉中COPs生成的影響……………......109 六、滷汁成分對滷蛋、滷肉及滷汁COPs生成的影響…………117 （一）添加醬油對滷蛋及滷肉中COPs生成的影響…….......117 （二）添加冰糖對滷蛋及滷肉中COPs生成的影響…….......129 （三）冰糖或醬油對滷蛋、滷肉及滷汁中COPs的影響........131 七、添加抗氧化劑對滷蛋及滷肉COPs生成的影響…………….137 （一）添加抗氧化劑對滷蛋中COPs生成的影響……….......137 （二）添加抗氧化劑對滷肉及滷汁中COPs生成的影響.......146 八、市售滷肉調查…………………………………………….......162 第五章結論…………………………………………………..........165 參考文獻………………………………………………………………167 圖目錄頁次圖一、膽固醇之結構……………………………………………………4 圖二、膽固醇氧化物結構圖....................................................................6 圖三、膽固醇自氧化的主要途徑............................................................17 圖四、膽固醇自氧化及光氧化之反應機制…………………………...19 圖五、膽固醇於不同油脂中氧化的情形………………………………21 圖六、膽固醇經不同溫度加熱之穩定度………………………………24 圖七、加熱溫度及時間對膽固醇氧化產物生成的影響………………25 圖八、加熱溫度及時間對膽固醇氧化產物生成的影響………………26 圖九、主要膽固醇氧化物於150 ℃加熱之生成量……………………28 圖十、α-生育醇及/或抗壞血酸對生鮮雞肉的總膽固醇氧化產物及TBA值影響………………………………...……………….30 圖十一、α-生育醇及/或抗壞血酸對熟雞肉的總膽固醇氧化產物及TBA值影響………...…………………..………………….31 圖十二、抗氧化劑於油相（a）及O/w乳化系統（b）中的分布情形……………………………..…………………………….33 圖十三、α-生育醇對肉鬆儲存期間膽固醇氧化產物生成的影響…....34 圖十四、肉製品內添加亞硝酸鈉及蘋果多酚的可能抗氧化機制…...36 圖十五、75 ℃下pH值對膽固醇氧化物裂解的影響………………...37 圖十六、四種分析膽固醇氧化產物方法之架構………………….…..42 圖十七、四種膽固醇氧化產物分析方法之結果比較…………….…..43 圖十八、糖以及糖/胺基酸混合物於不同加熱時間的褐變情形….….49 圖十九、糖以及糖/胺基酸混合物於100 ℃下加熱之加熱時間與清除自由基能力關係圖……………….………………….50 圖二十、不同加熱溫度對牛奶抗氧化活性影響………………………51 圖二十一、膽固醇及八種膽固醇氧化物標準品經三甲基矽烷衍生化後之氣相層析圖譜………………….……………….76 圖二十二、調整溫度梯度後之膽固醇及七種COPs標準品之 GC-MS-SIM層析圖………………………………….…...78 圖二十三之一. 7α-OH之GC-MS層析圖（A）和質譜圖（B）……80 圖二十三之二. 7β-OH之GC-MS層析圖（A）和質譜圖（B）……81 圖二十三之三. 5,6β-EP之GC-MS層析圖（A）和質譜圖（B）……82 圖二十三之四. 5,6α-EP之GC-MS層析圖（A）和質譜圖（B）……83 圖二十三之五. Triol之GC-MS層析圖（A）和質譜圖（B）………84 圖二十三之六. 25-OH之GC-MS層析圖（A）和質譜圖（B）…….85 圖二十三之七. 7-keto之GC-MS層析圖（A）和質譜圖（B）…….86 圖二十四、經NH2 cartridge純化後之滷肉萃出液氣相層析圖……..89 圖二十五、經NH2 cartridge純化後之滷蛋萃出液氣相層析圖……..90 圖二十六、滷蛋以silica cartridge進行純化後的GC-MS-SIM 層析圖…………….……………………………………….94 圖二十七、滷肉以silica cartridge進行純化後的GC-MS-SIM 層析圖………………….………………………………….95 圖二十八、滷肉之滷汁以silica cartridge進行純化後的 GC-MS-SIM層析圖………………………………………96 圖二十九、7種COPs標準品之迴歸曲線圖…………………………99 圖三十、7α-OH及7β-OH標準品之質譜圖…………………………..102 圖三十一、加熱時間對滷蛋中COPs生成的影響………………….107 圖三十二、白煮蛋之GC-MS-SIM層析圖………………………….108 圖三十三、加熱時間對滷肉中COPs生成的影響………………….111 圖三十四、加熱時間對滷肉之滷汁COPs生成的影響…………….115 圖三十五、滷肉之滷汁加熱四小時後的GC-MS-SIM層析圖….….116 圖三十六、經加熱十小時後的滷汁配方對滷蛋中COPs生成的影響…………………………………………………....119 圖三十七、添加10 %醬油與90 %水之滷蛋GC-MS-SIM層析圖………………………………….…………………...121 圖三十八、滷汁配方對滷肉中COPs生成的影響………………….126 圖三十九、滷汁配方對滷肉之滷汁COPs生成的影響…………….127 圖四十、添加10 %醬油之滷肉GC-MS-SIM層析圖……………....128 圖四十一、添加10 %冰糖之滷蛋GC-MS-SIM層析圖…………....130 圖四十二、添加抗氧化劑對滷蛋中COPs生成的影響………….…140 圖四十三、添加0.1 % BHA之滷蛋GC-MS-SIM層析圖……….…145 圖四十四、添加抗氧化劑對滷肉中COPs生成的影響………….…149 圖四十五、添加抗氧化劑對滷汁中COPs生成的影響………….…150 圖四十六、添加0.1 % 維生素C之滷肉GC-MS-SIM層析圖……151 圖四十七、添加0.1 % BHA之滷汁GC-MS-SIM層析圖……….…158 圖四十八、各抗氧化劑對滷味食品中COPs生成之抑制百分比….159 表目錄頁次表一、膽固醇氧化物對HMG-CoA還原酵素之影響…………….….9 表二、膽固醇氧化產物在動脈肌肉細胞培養液之細胞毒性……….10 表三、膽固醇氧化產物之細胞變異性……………………………….12 表四、膽固醇氧化時較常發生之化學反應………………………….14 表五、食品中膽固醇氧化產物定量可能出現之誤差……………….39 表六、牛奶經不同加熱溫度，時間的顏色變化…………………….52 表七、還原糖及總糖滴定計算對照表……………………………….71 表八、七種COPs以SIM模式偵測的質荷比……………………….87 表九、使用NH2 cartridge 純化白煮蛋中膽固醇及triol之回收率.........................................................................................91 表十、使用silica cartridge進行滷味與滷汁中COPs純化之回收率………………………………………………………….97 表十一、7種COPs標準物質之線性迴歸曲線與相關係數………..100 表十二、7種COPs於GC-MS-SIM偵測的偵測極限………………101 表十三、滷蛋、滷肉與滷汁中各COPs的偵測極限與定量極限………………………………..……………………...…104 表十四、加熱時間對滷蛋中COPs含量的影響………..…..………..106 表十五、加熱時間對滷肉中COPs含量的影響……………………..110 表十六、加熱時間對滷肉之滷汁中COPs含量的影響……………..114 表十七、經加熱十小時後的滷汁配方對滷蛋中COPs生成的影響……….………………………………………………118 表十八、不同滷汁配方的滷肉及滷蛋於加熱後的梅納反應指標變化……………….…………………………………...122 表十九、滷汁配方對滷肉中COPs生成的影響……………………124 表二十、滷汁配方對滷肉之滷汁中COPs生成的影響……………125 表二十一、不同滷汁配方的滷肉及滷蛋於加熱後的游離胺基酸含量變化………………………………….………...134 表二十二、不同滷汁配方的滷肉及滷蛋於加熱後的還原醣含量變化………………………………………….….…..135 表二十三、添加抗氧化劑對滷蛋中COPs生成的影響……….……139 表二十四、添加抗氧化劑對滷肉中COPs生成的影響……….……147 表二十五、添加抗氧化劑對滷汁中COPs生成的影響…….………148 表二十六、滷蛋及滷肉中各抗氧化劑殘留量………………….…….153 表二十七、各抗氧化劑對滷味食品中COPs生成之抑制百分比.……………………………………………………...160 表二十八、市售滷肉中COPs含量……………………………….…163
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