臺灣博碩士論文加值系統

雜環胺化合物(Heterocyclic amines,HAs)是由碳、氫、氮原子所組成，具有多環芳香族結構的化合物，其主要由食品中胺基酸、肌酸酐(creatinine)及糖類或直接由單一胺基酸或蛋白質經熱裂解而合成。由於大部份HAs具有致突變性或致癌性，且多發現於經油炸或燒烤等熱處理的高蛋白質食品中，如水產品及肉製品等，此類食品中的HAs含量高低已成為學界和消費者所關切的問題。本研究以自製魚鬆為模型，藉著在製造過程中對原料魚肉進行不同處理及添加不同成份，如味精、糖類、油脂與抗氧化劑等，以探討魚鬆製作過程中不同的處理方式與不同成份的添加對HAs生成之影響。
結果顯示，市售五種魚鬆所含的HAs種類以Norharman、Harman、PhIP、AC及MeAC為主。而自製之魚鬆所生成之主要HAs為Norharman、Harman、AC及MeAC。而影響carboline型之HAs生成的前驅物主要為葡萄糖與threonine、serine、leucine及phenylalanine四種胺基酸，其中以葡萄糖影響較為顯著。
在不同加工方法方面，以水煮或蒸煮為前處理時，HAs總生成量並無顯著差異，並且每一種HAs之生成量皆隨翻炒溫度升高而增加。在不同調味料添加量方面，以添加19 %之砂糖時，HAs總生成量最低，其中以Norharman生成量最低；隨著味精添加量增加，HAs生成量亦增加，尤以Norharman增加最多。在抗氧化劑方面，添加高濃度ascorbic acid時，對魚鬆AC及MeAC的生成有顯著的抑制效果；添加低濃度-tocopherol（0.1克）時，對HAs有抑制效果，其中又以Norharman和MeAC之抑制更為顯著；而低濃度BHT會促進Norharman、Harman及MeAC生成，高濃度BHT則對Norharman、Harman、AC及MeAC皆有抑制效果。
在儲存溫度方面：以鋁箔袋包裝儲存時，HAs生成量隨儲存溫度上升而增加；以塑膠袋儲存時，儲存溫度與HAs總生成量，則無顯著差異。在儲存時間方面：不論是以鋁箔或塑膠袋包裝時，HAs總生成量隨儲存時間增加而降低。在添加不同油脂方面：HAs總生成量以添加椰子油時最高，其次為添加豬油；而添加大豆油時，HAs生成量遠低於添加豬油時之HAs生成量。

Heterocyclic amines (HAs) are a group of compounds with unsaturated double bonds and ring structure that are composed of carbon, hydrogen and nitrogen. The major mechanism of HAs formation can be attributed by heating of four precursors, amino acids, creatine, creatinine and sugar, or by pyrolyzing of amino acids and proteins. Previous researches have shown that some HAs are mutagenic and carcinogenic. Frying or broiling of meat and other protein-rich foods, such as fish and beef may generate several HAs. The consumption of HAs in excess is harmful to human health. This study used shredded fried fish as a model to investigate various processing treatments and food additives, such as monosodium glutamate, sugars, oils and antioxidants, on HAs formation.
Results showed that Norharman, Harman, PhIP, AC and MeAC were found in shredded fried fish of five commercial brands. In the lab-made shredded fried fish, four HAs, Norharman, Harman, AC and MeAC, were present.
The total levels of HAs in shredded fried fish pretreated by boiling or steaming were not significant (p>0.05). The yield of each HAs increased with increasing heating temperature. High amount of HAs was found in shredded fried fish of 1.5 % monosodium glutamate. The HAs content increased with increasing amount of monosodium glutamate, however, high level of sugar (19 %) inhibited formation of both AC and MeAC. Likewise, high level of ascorbic acid inhibited formation of both AC and MeAC, while low level of -tocopherol (0.1 g) inhibited production of four HAs, Norharman, Harman, AC and MeAC. Also, low level of BHT (0.1 and 0.5g) accelerated formation of Norharman, Harman, AC and MeAC, but high level of BHT (1.0g) inhibited formation of Norharman and MeAC.
During storage, the HAs increased with increasing storage temperature when shredded fried fish was packed in aluminum foil , however, the difference was not significant (p>0.05) between storage temperature and HAs formation when shredded fried fish as packed in plastic bag. When packed with aluminum foil or plastic bags, the HAs decreased with increasing storage time. HAs was formed in largest amount in shredded fried fish of coconut oil, origin, followed by lard and soybean oil.

頁次
第一章 緒 言……………………………………………………….1
第二章 文獻回顧…………………………………………………..3
一、雜環胺化何物的簡介與生成…………………………………3
（一） 由前驅物合成的HAs……………………………………..3
（二） 直接由胺基酸或蛋白質經熱裂解生成的HAs…………..6
二、HAs的分析……………………………………………………10
三、HAs的生物毒性………………………………………………12
四、HAs的萃取純化………………………………………………16
五、食品中HAs生成的影響因子………………………………..21
（一） 加熱溫度對HAs生成的影響…………………………….21
（二） 加熱時間對HAs生成的影響…………………………….21
（三） 不同熱加工方法對HAs形成的影響…………………….27
1. 烹煮、烘烤、燒烤…………………………………………27
2. 浸泡滷汁……………………………………………………27
3. 煙薰…………………………………………………………30
（四） 食品中水含量對HAs生成的影響……………………….30
（五） 食品中脂肪含量對HAs生成的影響……………………..33
六、抑制食品中HAs生成之探討…………………………………37
（一） 抗氧化劑…………………………………………………….37
（二） 葡萄糖及乳糖……………………………………………….40
七、肉製品經加熱處理所生成的HAs………………………………43
八、魚肉經加熱處理所生成的HAs………………………………….46
第三章 材料與方法……………………………………………………50
一、實驗材料………………………………………………………….50
﹙一﹚ 魚種/添加物…………………………………………………..50
﹙二﹚ 試劑/藥品……………………………………………………..50
﹙三﹚ 儀器設備………………………………………………………52
二、實驗方法………………………………………………………….54
﹙一﹚ 市售肉鬆和魚鬆的HAs含量調查…………………………..54
﹙二﹚ 魚肉加工………………………………………………………54
1. 前處理…………………………………………………………..54
2. 翻炒…………………………………………………………….54
3. 基本配方……………………………………………………..55
4. 魚肉烹煮方法與翻炒溫度…………………………………..55
5. 不同糖量………………………………………………………..56
6. 不同味精量……………………………………………………..56
7. 不同抗氧化劑…………………………………………………..56
8. 不同油脂……………………………………………………56
9. 魚鬆儲存測試………………………………………………57
（三）魚鬆中HAs之萃取………………………………………57
（四）葡萄糖含量……………………………………………..58
（五）胺基酸分析………………………………………………59
1. 萃取…………………………………………………………59
2. 定量…………………………………………………………59
（六）HPLC分析HAs之條件………………………………………60
（七）HAs的鑑定…………………………………………………..61
﹙八﹚HAs的定量………………………………………………….61
﹙九﹚統計分析……………………………………………………62
第四章 結果與討論………………………………………………63
一、市售魚鬆的HAs含量調查 …………………………………63
二、不同魚肉處理方式對魚鬆HAs含量的影響…………………..67
三、添加不同成份對魚鬆HAs含量的影響…………………………83
（一）添加不同糖量對魚鬆HAs含量的影響………………………83
（二）添加不同味精量對魚鬆HAs含量的影響……………………89
四、添加不同抗氧化劑對魚鬆HAs含量的影響…………………..96
（一）添加維生素C對魚鬆HAs含量的影響……………………97
（二）添加維生素E對魚鬆HAs含量的影響……………………..97
（三）添加BHT對魚鬆HAs含量的影響………………………..100
五、魚鬆儲存對HAs含量的影響…………………………………..103
六、添加不同油脂對魚鬆HAs含量的影響………………………..107
第五章 結 論……………………………………………………110
參考文獻……………………………………………………………112
表目錄
表一 不同胺基酸生成HAs及有糖、無糖下產生致突變性得情形…5
表二 由蛋白質及胺基酸熱裂所產生Carboline型HAs的結構……..9
表三 由前趨物生合成IQ型HAs的致突變性……………………….13
表四 HAs誘發老鼠體內致癌之器官………………………………15
表五 HAs以老鼠測試之TD50值……………………………………..17
表六 烤牛肉中生成HAs化合物及其產生的致突變活性…………..23
表七 油炸牛肉餅中HAs的生成量(ng/g) …………………………24
表八 加熱時間及厚度對牛肉中致突變物質生成之影響…………25
表九 不同食品經烹調後生成之HAs………………………………32
表十 烘烤肉泥捲的實驗條件………………………………………34
表十一 比較高脂肪及低脂肪牛肉的致突變性……………………38
表十二 牛餅的組成、油炸失重、添加乾料及表面生成物質的致突變活性……………………………………………………….41
表十三 不同加熱溫度對食品中MeIQx、DiMeIQx及PhIP生成的影響…………………………………………………………44
表十四 不同加熱溫度對食品中Trp-P-1、Trp-P-2、harman及norharman HAs生成的影響……………………………….45
表十五 加熱肉製品生成之HAs……………………………………47
表十六 平均每日從肉製品攝食HAs之含量……………………49
表十七 五種市售魚鬆HAs含量(ng/g) …………………………..64
表十八 五種市售魚鬆之葡萄糖、胺基酸及HAs含量….66
表十九 五種市售魚鬆胺基酸含量 (mg/100g)…………………..69
表二十 水煮與蒸煮魚經不同溫度翻炒製成之魚鬆HAs生成量(ng/g)………………………………………………………73
表二十一 經水煮及蒸煮的魚分別以100℃、120℃及140℃翻炒後之魚鬆葡萄糖、胺基酸與HAs含量……………………77
表二十二 水煮與蒸煮魚經不同溫度翻炒製成之魚鬆其胺基酸含量(mg/100g) ……………………………………………….79
表二十三 生魚、經水煮後的魚及以基本配方翻炒後魚鬆的胺基酸含量(mg/100g)……………………………………………80
表二十四 添加不同糖量之魚鬆HAs生成量(ng/g)…………………84
表二十五 添加不同糖量翻炒之魚鬆其葡萄糖、胺基酸與HAs含量…………………………………………………………86
表二十六 添加不同糖量魚鬆之胺基酸含量(mg/100g)……………88
表二十七 添加不同味精量之魚鬆HAs生成量(ng/g)………………92
表二十八 添加不同味精量翻炒之魚鬆其葡萄糖、胺基酸與HAs含量…………………………………………………………..93
表二十九 添加不同味精量魚鬆之胺基酸含量(mg/100g)…………95
表三十 添加不同維生素C量之魚鬆HAs生成量(ng/g)………….98
表三十一 添加不同維生素E量之魚鬆HAs生成量(ng/g)……….99
表三十二 添加不同BHT量之魚鬆HAs生成量(ng/g)……………101
表三十三 魚鬆儲存對HAs生成之影響……………………………105
表三十四 添加不同油脂之魚鬆HAs生成量(ng/g)……………….108
圖目錄
圖一 IQ型HAs之生合成機制………………………………………..4
圖二 由前趨物生成IQ型HAs的結構……………………………….7
圖三 tryptophan與glutamic acid的熱分解產物………………………8
圖四 IQ型HAs的活化機制……………………………………… 14
圖五 HAs的極性分類結構…………………………………………..19
圖六 HAs的萃取純化流程…………………………………………..20
圖七 評估100g油炸肉品及其鍋內殘留物於不同溫度下HAs之含量變化………………………………………………………….22
圖八 加熱時間對豬肉餅中致突變物質生成之影響………………..26
圖九 食品經不同加工方式生成之致突變性物質…………………..28
圖十 肉類食品經不同製備方式致突變性物質生成之影響………..29
圖十一 雞胸肉燒烤前經浸泡滷汁對HAs生成之影響…………….31
圖十二 不同脂質含量及溫度對烘烤肉泥致突變物質生成的影響..35
圖十三 牛肉中脂肪含量對致突變活性的影響……………………..36
圖十四 模式系統中不同的抗氧化劑對MeIQx 生成的影響………39
圖十五 牛肉餅表面生成致突變物質之抑制………………………..42
圖十六 肉脯型乾燥機………………………………………………..53
圖十七 E品牌胺基酸層析圖……………………………………….68
圖十八 自製之魚鬆…………………………………………………70
圖十九 水煮後以不同溫度翻炒魚鬆HAs萃取液之高效率液態層析圖……………………………………………………………71
圖二十 蒸煮後以不同溫度翻炒魚鬆HAs萃取液之高效率液態層析圖…………………………………………………………….72
圖二十一 添加不同味精量翻炒之魚鬆HAs萃取液之高效率液態層析圖………………………………………………………..91

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