記錄 編號 11364 狀態 G0497856066 助教 查核 建檔完成 索書 號
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記錄 編號 11364 狀態 G0497856066 助教 查核 建檔完成 索書 號 查核完成 學校 名稱 輔仁大學 系所 名稱 食品科學系 舊系 所名 稱 學號 497856066 研究 陳怡君 生(中) 研究 Chen Yi Chun 生(英) 論文 名稱 (中) 論文 名稱 (英) 豬腳滷煮過程中膽固醇氧化物之生成與抑制 Formation and inhibition of cholesterol oxidation products during marinating of pig legs 其他 題名 指導 教授 (中) 陳炳輝 指導 教授 (英) Chen Bing Huei 校內 全文 開放 日期 2012.7.11 校外 全文 2012.7.11 開放 日期 全文 不開 放理 由 電子 全文 同意 送交 國圖. 國圖 全文 2012.7.11 開放 日期. 檔案 說明 論文全文 電子 全文 01 學位 類別 碩士 畢業 學年 度 100 出版 年 100 語文 別 中文 關鍵 豬腳 膽固醇氧化物 滷煮 字(中) 關鍵 pig legs cholesterol oxidation products marinated 字(英) 摘要 (中) 豬肉含有高量之脂肪及膽固醇，於加熱過程中易形成脂質氧化物及膽固 醇氧化物(cholesterol oxidation products, COPs)。許多文獻指出攝食過量脂 質氧化物及 COPs 可能會導致心血管疾病、肝功能病變及致突變性。豬 腳一般使用醬油及冰糖經長時間滷製而成，而滷煮過程中生成之梅納反 應產物，可能具有抑制脂質及膽固醇氧化的效果。本研究目的為發展以 氣相層析儀搭配火焰離子偵檢器(GC-FID)及質譜儀(GC-MS)分析豬腳及滷 汁之脂肪酸、膽固醇及 COPs 的方法，並探討豬腳於不同加熱時間對脂 肪酸、膽固醇及 COPs 安定性之影響。 結果顯示，以 HP-5MS (30 m × 0.25 mm I.D., 0.25 μm thickness)管柱搭配 GC-MS，配合氦氣流速 0.7 mL/min，注射分流比 5:1，注射口溫度 280℃，管柱起始溫度 220℃，維 持 2 分鐘，以每分鐘 50℃升溫至 280℃，再以每分鐘 4℃升溫至 289℃， 維持 9 分鐘，最後以每分鐘 1℃升溫至 295℃，並維持 10 分鐘，GC-MS 介面溫度為 300℃，此條件可於 15 分鐘內分離出膽固醇、7 種 COPs 及 內部標準品 5-α cholestane；以 HP-88 (100 m × 0.25 mm I.D., 0.2μm film thickness)管柱搭配 FID，配合氦氣流速 2.5 mL/min，注射分流比 20:1，注 射口溫度 240℃，管柱起始溫度 166℃，以每分鐘 0.5℃升溫至 175℃， 維持 4 分鐘，最後以每分鐘 5℃升溫至 225℃，維持 8 分鐘，偵檢器溫度 為 250℃，此條件可於 39 分鐘內分離出 20 種脂肪酸。長時間加熱均會 導致豬腳皮層、肉層及滷汁中 COPs 含量增加。除了 8 和 12 小時之皮層 COPs 含量較肉層高外，其餘加熱時間點均以肉層的 COPs 含量最高，加 熱至 24 小時，肉層、皮層及滷汁之總 COPs 含量分別為 1565.5、1497.8 及 1357.4 ng/g；皮層及肉層之脂肪酸無顯著變化，而滷汁之多元不飽和 脂肪酸有隨之下降的趨勢。豬腳皮層、肉層及滷汁之褐變指標會隨著滷 煮時間增加而增加；加熱至 8 小時，滷汁之 pH 值略為下降，之後隨著 滷煮時間增長而增加。皮層及肉層之游離胺基酸隨著滷煮時間增長而增 加，但加熱至 24 小時，則有下降之趨勢，滷汁之游離胺基酸會隨著滷 煮時間增加而增加。皮層之還原糖無顯著變化，肉層之還原糖會隨著滷 煮時間增加而略為增加，滷汁於加熱 0 - 4 小時間，還原糖含量會隨之下 降，但加熱 8 小時後的含量會上升。相較於未添加之控制組，滷汁中添 加醬油及冰糖均可抑制豬腳皮層、肉層及滷汁中 COPs 之生成。 摘要 (英) Lipid oxidation products (LOPs) and cholesterol oxidation products (COPs), formed during heating of lipid and cholesterol-rich food products like pig leg, have been shown to cause coronary heart disease, liver damage and mutagenicity. In general pig legs are processed by marinating in soy sauce and crystal sugar, which may be susceptible to formation of high amount of LOPs and COPs after prolonged heating. However, the formation of Maillard reaction products during heating may inhibit formation of both lipid and cholesterol oxidation products. The objectives of this study were to develop a GC-FID and GC-MS method to analyze fatty acid, cholesterol and COPs in pig legs and marinated juices, and study the effect of heating time on stability of fatty acid and COPs. Results showed that an HP-5MS column could provide an adequate separation of cholesterol, 7 COPs and internal standard (5α-cholestane) within 15 min with helium as carrier gas at a flow rate of 0.7 mL/min, split ratio 5:1 and injector temperature 280oC. The column temperature was programmed as follows: 220oC initially, maintained for 2 min, raised to 280oC at 50oC/min, 289oC at 4oC/min, maintained for 9 min and further to 295oC at 1oC/min and maintained for 10 min. The GC-MS interface temperature was 300oC. For separation of fatty acids, a HP88 column (100m × 0.25mm I.D. × 0.2 μm film thickness) was employed and a total of 20 fatty acids could be adequately separated within 39 min with helium gas at a flow rate of 2.5 mL/min, split ratio 20:1 and injector temperature 240oC. The column temperature was programmed as follows: 166oC initially, raised to 175oC at 0.5oC/min, maintained for 4 min and further to 225oC at 5oC/min and maintained for 8 min, with the detector temperature at 250oC. With the exception of 8 and 12 h heating, the COPs in lean portion was generated at a larger amount than in skin portion and marinated juice. However, at 8 and 12 h heating, the formation of COPs in skin portion was higher than in lean portion. After 24 h of heating, the levels of total COPs in lean, skin and marinated juice reached 1565.5, 1497.8 and 1357.4 ng/g, respectively. For fatty acids, the contents did not show significant change in both skin and lean portions during heating. Nevertheless, following a rise in heating time, the levels of polyunsaturated fatty acids decreased in marinated juice. Likewise, the Maillard browning index rose with increasing heating time. The pH in marinated juice slightly dropped over a heating period of 8 h, but soared thereafter. The free amino acids in skin and lean portions showed an increased trend over a heating period over of 12 h, but declined after extensive heating to 24 h. The levels of free amino acids in marinated juice showed a similar tendency, but a peak was attained in 24 h. The contents of reducing sugar showed no significant change during heating of skin portion of pig legs, whereas a slight increase found for lean portion of pig legs. In contrast, the reducing sugar levels diminished in marinated juice during initial 4 h of heating, but rose again after 8 h heating. Compared to control treatment, the incorporation of soy sauce and crystal sugar in marinated juice was efficient in inhibiting COPs formation in skin and lean portions of pig legs as well as in marinated juice. 論文 目次 第一章 緒言 1 第二章 文獻回顧 3 一、脂肪酸的簡介 3 (一) 飽和脂肪酸 3 (二) 不飽和脂肪酸 3 二、影響油脂氧化的因子 4 (一) 食品組成分 4 (二) 熱處理 4 (三) 抗氧化劑 12 (四) 貯存條件 16 (五) 光照及輻射 16 三、脂質 相關之化學反應機制 17 (一) 油脂自氧化反應 17 (二) 光氧化作用 18 (三) 熱氧化作用 19 (四) 輻射照射 19 (五) 聚合作用 20 四、脂質對人體的影響 20 (一) 皮膚的影響 20 (二) 出血與凝血的調節 21 (三) 心血管疾病 21 (四) 肝功能影響 22 (五) 致突變與致癌性 23 五、脂肪酸萃取、定性與定量分 析 25 (一) 萃取 25 (二) 定性與定量分析 27 六、膽固醇簡介 31 七、膽固 醇氧化物簡介 31 八、影響膽固醇氧化的因子 34 (一) 食品組成分 34 (二) 熱處理 34 (三) 抗氧化劑 37 (四) 貯存條件 37 (五) 酸鹼值 40 (六) 光照及 輻射 40 九、膽固醇氧化機制 41 (一) 自氧化反應 41 (二) 光氧化反應 43 (三) 酵素性氧化反應 43 十、膽固醇氧化物的生理活性 47 (一) 心血管疾 病 47 (二) 致突變與致癌性 49 (三) 細胞毒性 50 (四) 抑制酵素活性 51 十 一、膽固醇氧化物的萃取、定性與定量分析 51 (一) 分離與純化 51 (二) 定量及定性分析 53 十二、豬隻簡介 56 第三章 材料與方法 68 一、研究 架構 68 二、材料與儀器 69 (一) 原料 69 (二) 試料暨材料 69 (三) 儀器設 備 71 三、實驗方法 74 (一) 水分含量測定 74 (二) 豬腳之膽固醇、COPs 及脂肪酸之萃取純化 74 (三) 膽固醇、COPs 及脂肪酸甲酯分離條件 77 (四) 分析方法精密度檢定 78 (五) 膽固醇、COPs 及脂肪甲酯酸鑑定方法 79 (六) 膽固醇及 COPs 標準曲線的建立 81 (七) 偵測極限與定量極限 81 (八) 回收率的測定 82 (九) 膽固醇、COPs 及脂肪酸之定量 82 (十) 滷煮時 間對豬腳中膽固醇、COPs 及脂肪酸含量變化的影響 83 (十一) 豬腳皮 層、肉層及滷汁中還原糖含量分析 84 (十二) 豬腳皮層、肉層及滷汁中殘 留胺基態氮分析 86 (十三) 豬腳皮層、肉層及滷汁中褐變指標測定 87 (十 四）統計分析 87 第四章 結果與討論 88 一、標準品的選擇 88 二、分析 方法之確立 89 三、豬腳中脂肪酸、COPs 及膽固醇之萃取與純化 115 四、標準曲線的建立 127 五、偵測極限及定量極限 127 六、加熱時間對 豬腳及滷汁中膽固醇及 COPs 變化之影響 137 七、滷汁成分對滷豬腳 COPs 生成的影響 149 八、加熱時間對豬腳及滷汁中脂肪酸變化之影響 156 第五章 結論 167 參考文獻 169 圖目錄 圖一、油炸過程中脂質氧化途 徑 7 圖二、油炸過程中油脂氧化反應之產物 9 圖三、油炸過程中油脂水 解反應之產物 10 圖四、橄欖油及葵花油分別對油酸下降量與 monoepoxystearates 之相關 性(A)及亞麻油酸下降量與 monoepoxyoleates 之 相關性(B) 14 圖五、使用氣相層析之 HP-88 管柱分離脂肪酸甲基酯標準 品 30 圖六、膽固醇之結構 32 圖七、膽固醇於磷脂質中構成細胞膜之位 置 33 圖八、常見的膽固醇氧化物結構 35 圖九、膽固醇自氧化的主要途 徑 44 圖十、環氧基膽固醇及 triol 之形成 45 圖十一、光氧化之反應機制 46 圖十二、四種膽固醇氧化產物分析方法之結果比較 54 圖十三、不同 組合生成之 MRPs 於 420nm 測得之吸光值 64 圖十四、儲存於 5 OC 下亞 麻油酸甲酯系統中生成 MRPs 之 TBARS 值 65 圖十五、葡萄糖之線性迴 歸曲線圖 85 圖十六、以 HP-88 管柱分析脂肪酸甲基酯標準品之氣相層 析圖 91 圖十七、調整溫度梯度後以 HP-88 管柱分析脂肪酸甲基酯標準 品之氣相層析圖 92 圖十八之一、以 HP-88 管柱分析豬腳皮層(滷煮 2 小 時)之脂肪酸氣相層析圖 95 圖十八之二、以 HP-88 管柱分析豬腳皮層(滷 煮 24 小時)之脂肪酸氣相層析圖 96 圖十九之一、以 HP-88 管柱分析豬腳 肉層(滷煮 2 小時)之脂肪酸氣相層圖 97 圖十九之二、以 HP-88 管柱分析 豬腳肉層(滷煮 24 小時)之脂肪酸氣相層析圖 98 圖二十之一、以 HP-88 管柱分析滷汁(滷煮 2 小時)之脂肪酸氣相層析圖 99 圖二十之二、以 HP88 管柱分析滷汁(滷煮 24 小時)之脂肪酸氣相層析圖 100 圖二十一、以 HP-5MS 管柱分析之膽固醇及七種 COPs 標準品和內部標準品之 GC-MSSIM 層析圖 102 圖二十二、調整梯度後之膽固醇及七種 COPs 標準品之 GC-MS-SIM 層析圖 104 圖二十三之一、C10:0 及 C12:0 的 GC-MS 質譜圖 105 圖二十三之二、C14:0 及 C16:0 的 GC-MS 質譜圖 106 圖二十三之 三、C16:1 9c 及 C17:0 的 GC-MS 質譜圖 107 圖二十三之四、C18:0 及 C18:1 9c 的 GC-MS 質譜圖 108 圖二十三之五、C18:1 11c 及 C18:2 9c,12c 的 GC-MS 質譜圖 109 圖二十三之六、C20:0 及 C18:3 9c 12c15c 的 GC-MS 質譜圖 110 圖二十三之七、C20:1 11c 及 C20:2 11c 14c 的 GC-MS 質譜圖 111 圖二十三之八、C20:3 8c11c14c 及 C20:4 5c8c11c14c 的 GC-MS 質譜圖 112 圖二十三之九、C20:5 5c8c11c14c17c 及 C22:4 7c10c13c16c 的 GC-MS 質譜圖 113 圖二十三之十、C22:5 7c10c13c16c19c 及 C22:6 4c7c10c13c16c19c 的 GC-MS 質譜圖 114 圖二十四之一、 7α-OH 及 cholesterol 的 GC-MS-TIC 質譜圖 116 圖二十四之二、 7β-OH 及 5,6βepoxide 的 GC-MS-TIC 質譜圖 117 圖二十四之三、5,6α-epoxide 及 triol 的 GC-MS-TIC 質譜圖 118 圖二十四之四、25-OH 及 7-keto 的 GC-MS-TIC 質 譜圖 119 圖二十五、豬腳滷煮 2 小時(a)及 24 小時(b)之皮層以 silica cartridge 進行純化後之 GC-MS-SIM 層析圖 128 圖二十六、豬腳滷煮 2 小 時(a)及 24 小時(b)之肉層以 silica cartridge 進行純化後之 GC-MS-SIM 層析 圖 129 圖二十七、豬腳滷煮 2 小時(a)及 24 小時(b)之滷汁以 silica cartridge 進行純化後之 GC-MS-SIM 層析圖 130 圖二十八、豬腳之皮層(a)及肉層 (b)以 silica cartridge 進行純化後之 GC-MS-SIM 層圖 131 圖二十九、豬腳 之滷汁以 silica cartridge 進行純化後之 GC-MS-SIM 層析圖 132 圖三十、 七種 COPs 及膽固醇標準品之迴歸曲線圖 133 表目錄 表一、油炸過程中 油脂之物理及化學性的影響 5 表二、不同因子對家庭用油於加熱過程中 化合物之生成 8 表三、高油酸葵花油及葵花油油炸冷凍食品 20 次後， 轉變的脂肪酸、極性物質、聚合物及氧化三酸甘油脂的含量變化 11 表 四、橄欖油及葵花油之非極性脂肪酸甲基酯含量及脂肪酸組成變化 13 表五、橄欖油及葵花油於 180°C 加熱 5、10 及 15 小時，極性脂肪酸甲基 酯及脂肪酸聚合物、二聚體及氧化單體含量之分佈情形 15 表六、亞麻 油酸甲酯氧化產物之分佈 24 表七、餵食大鼠未油炸之葵花油(1)及油炸 過之葵花油(2)，其體重、攝食量、蛋白質吸收率、脂質及修飾脂肪攝取 含量情形 26 表八、不同烹調處理對 7-ketocholesterol 含量及總膽固醇中 7-keto- cholesterol 含量百分比之影響 38 表九、滷蛋、滷肉及滷汁在滷煮 過程中 COPs 之含量變化 39 表十、火雞肉於 4℃不同光照環境下儲存 11 天之 CLA 及過氧化價的變化 42 表十一、酵素性與非酵素性膽固醇氧化 物之縮寫式、一般式及分類命名 48 表十二、乳豬及成熟豬肉中脂肪酸 之組成變化 58 表十三、乳豬及成熟豬中總脂質及膽固醇含量變化 59 表 十四、乳豬及成熟豬之皮層及背脂部位脂肪酸組成變化 60 表十五、經 乾燥、乾燥後經去鹽及水煮或經去鹽、水煮及真空包裝之前腿肉之皮下 脂肪組織的化學及脂肪組成 62 表十六、豬腳前腿肉的化學組成及物化 參數 63 表十七、含有豬肉餡餅之發酵大豆及黑豆湯汁於 125oC 加熱前 及加熱 2 小時後游離胺基酸之組成 67 表十八、以二十種脂肪酸甲酯標 準品測得之分析精密度 80 表十九、二十種脂肪酸甲酯標準品之滯留時 間、滯留常數及分離度 94 表二十、七種 COPs 及膽固醇以 SIM 模式偵測 的質荷比 120 表二十一、豬腳的皮層、肉層和滷汁之萃取及甲基酯化回 率 123 表二十二、使用 silica cartridge 進行豬腳皮層、肉層及滷汁中 COPs 和膽固醇純化之回收率 126 表二十三、七種 COPs 及膽固醇標準物 質之線性迴歸曲線與相關係數 134 表二十四、7 種 COPs 與膽固醇於 GCMS-SIM 偵測的偵測極限及定量極限 136 表二十五、加熱時間對豬腳中 膽固醇含量之影響 138 表二十六、加熱時間對豬腳及滷汁中水分含量之 變化 140 表二十七、加熱時間對豬腳皮層中 COPs 含量的影響 143 表二 十八、加熱時間對豬腳肉層中 COPs 含量的影響 146 表二十九、加熱時 間對豬腳滷汁中 COPs 含量的影響 150 表三十、加熱時間對豬腳及滷汁 中 pH 值和褐變指標之變化 152 表三十一、加熱時間對豬腳及滷汁之還 原糖及游離胺基態氮含量之影響 154 表三十二、加熱時間對豬腳皮層中 脂肪酸組成變化 159 表三十三、加熱時間對豬腳肉層中脂肪酸組成變化 160 表三十四、加熱時間對滷汁中脂肪酸組成變化 164 參考 文獻 Sci 77: 114-120. 沈松茂。1995。食物原料與烹調技術。中華民國餐飲學 會出版。台北。 沈添富。1996。部編大學用書畜產學。合記圖書出版 社。台北。 張為憲。1995。食品化學。P71-108。華香園出版社。台北。 廖婉如。1994。生物檢體內脂質過氧化物之分析評估及相關生理研究。 靜宜大學食品營養學系研究所碩士論文。台中。 陳冀。2000。甘藷桃園 二號對鹽分逆境之抗氧化物質的生化反應研究。國立中央大學生命科學 研究所碩士論文。桃園。 王智琦。2004。MAP Kinases, Akt 以及 eNOS 等 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