臺灣博碩士論文加值系統

梅納反應 (Maillard reaction) 是常出現在食品加工過程中的一種非酵素性褐變現象 (Non-enzymatic browning)，並將造成致癌物質─丙烯醯胺 (Acrylamide) 的產生。而在近來的研究中發現，由於幾丁聚醣 (Chitosan) 具有胺基，使其能與還原醣進行梅納反應，因此本實驗選用不同分子量之幾丁聚醣 (50~190 kDa、190~310 kDa、310~375 kDa) 與果糖 (Fructose)、天門冬醯胺酸 (Asparagine) 進行反應，探討其抑制果糖與天門冬醯胺酸產生丙烯醯胺的效果，並觀察所生成之梅納反應產物 (Maillard reaction products, MRPs) 於功能特性上的差異。將果糖 與天門冬醯胺酸 (F+A)、果糖與低、中、高分子量之幾丁聚醣 (F+LC、F+MC、F+HC)、果糖合併天門冬醯胺酸與幾丁聚醣 (F+A+LC、F+A+MC、F+A+HC) 及單獨含有反應物 (F、A、LC、MC、HC) 的各組溶液於 180℃ 下反應 30 分鐘後，檢測其中丙烯醯胺的含量，並進行吸光值、色差值、pH 值、黏度及抗氧化力、抗菌性等試驗。在吸光值方面，結果發現以果糖與幾丁聚醣反應的組別，其不論是在 294 nm 或 420 nm 下，吸光值皆較低，表示褐變產物的生成量較少，而加入天門冬醯胺酸共同反應後，其褐變產物含量則高於其他各組；在丙烯醯胺含量測定上，則發現幾丁聚醣的添加可降低丙烯醯胺生成，並以低分子量幾丁聚醣具有最佳的效果。另外在色差值方面，不論有無胺基酸的添加，在各個混合反應的組別當中，皆呈現出偏紅及偏黃的色澤，但其中以 F+A+LC、F+A+MC、F+A+HC 及 F 組具有較高的 a* 值，而 b* 值的部分則以 F+LC、F+MC 與 F+HC 組為最高；於 pH 值的部分則發現混合反應的各組溶液在其反應後皆有顯著下降的情形，但卻未隨幾丁聚醣分子量的改變而有所差異，在色差及黏度測定上也有同樣的現象；另外在自由基清除能力、亞鐵離子螯合力及還原力等抗氧化實驗的測定結果中，發現各個實驗組皆具抗氧化活性，但其中以三者共同反應的組別具有較強的抗氧化效果。而利用吸光值、丙烯醯胺含量、色差值及抗氧化試驗的實驗數據進行相關性分析後，結果顯示丙烯醯胺的生成量是與吸光值間具有較強烈的正相關性。最後在抗菌性方面，可發現混合反應的組別對於大腸桿菌 (Escherichia coli) 及仙人掌桿菌 (Bacillus cereus) 的抑菌效果皆不佳，無法在培養基上產生抑菌環的現象。以上結果顯示幾丁聚糖能應用於抑制梅納反應中丙烯醯胺的生成，而其所產生的梅納反應產物溶液在各項物理特性上並不隨幾丁聚醣分子量的差異而有所改變，並且同時能具有抗氧化的效果，期望未來可將幾丁聚醣應用於食品當中，以抑制毒性物質的生成，並賦予食品抗氧化等良好的特性。

Maillard reaction is a kind of non-enzymatic browning reaction that usually occurs in food processing. During the reaction, acrylamide (a potential carcinogen) will also be produced. Recent study found that chitosan contains amino groups which can react to reducing sugar, allowing it to interfere in Maillard reaction. In this research, different-molecular-weights chitosan (50~190 kDa, 190~310 kDa, and 310~375 kDa) were reacted with fructose and asparagine and the ability to inhibit acrylamide formation as well as difference in functional properties of the products were observed. The experiment was done by reacting fructose with asparagine (F+A), fructose with low-, medium-, and high-molecular-weight chitosan, (F+LC, F+MC, F+HC), and combination of both fructose and asparagine with low-, medium-, and high-molecular-weight chitosan, (F+A+LC, F+A+MC, F+A+HC). Each reactants were also prepared singly. All solutions were then heated at 180℃ for 30 min and analyzed for their acrylamide amount, absorbance, color, pH, kinematic viscosity, antioxidant power, and antibacterial activity. Fructose reacted with different-molecular-weight chitosan gave low absorbance values at OD294 and OD420, indicating less formation of Maillard reaction products compared to other mixtures. On the other hand, combination of fructose and asparagine reacted with different-molecular-weight chitosan resulted in more MRPs than other mixtures. Chitosan, especially low-molecular-weight chitosan, was proven capable of reducing the acrylamide content. Adding asparagine to fructose and chitosan mixtures constantly turned the solution’s colors to red and yellow after 180℃ heating. F+A+LC, F+A+MC, F+A+HC and F solutions gave higher a* values while F+LC, F+MC, F+HC gave higher b* values. After Maillard reaction, the pH value in mixture solutions decreased significantly but no significant difference was found among different-molecular-weights chitosan. Similarly, the color and viscosity of different-molecular-weights chitosan also showed no significant difference.
1,1-diphenyl- 2-pricrylhydrazyl (DPPH) radical scavenging activities, ferrous ion chelating abilities and reducing power results showed that every solution had antioxidant power, with the solutions containing combination of three reactants being the most powerful of all. Acrylamide content was found to have a strong-positive correlation with absorbance value. Zone-of-inhibition test showed that products of Maillard reaction did not have the ability to inhibit the growth of Escherichia coli and Bacillus cereus. This experiment indicates that chitosan can be used to inhibit the formation of acrylamide. All products of Maillard reaction showed antioxidant power with no statistical differences found in color, pH, and viscosity values between products of Maillard reactions prepared with different-molecular-weights chitosan. In the future, chitosan has a big potency in food system application for inhibiting the formation of toxic substances and increasing food property such as antioxidant power.

目次
摘要....................................................I
Abstract...............................................II
目次...................................................IV
圖目次................................................VII
表目次...............................................VIII
附錄...................................................IX
壹、 前言................................................1
貳、 文獻回顧............................................2
一、 梅納反應............................................2
1.1 簡介................................................2
1.2 影響梅納反應的因素....................................2
二、 梅納反應產物特性.....................................4
2.1 簡介................................................4
2.2 梅納反應產物之抗氧化性................................4
2.3 梅納反應產物之抗菌性..................................4
三、丙烯醯胺.............................................5
3.1 丙烯醯胺的物化特性....................................5
3.2 丙烯醯胺的毒性.......................................5
3.2.1 生殖毒性...........................................6
3.2.2 基因毒性...........................................6
3.2.3 神經毒性...........................................6
3.2.4 致癌性............................................7
3.3 食品中的丙烯醯胺......................................7
3.3.1 梅納反應...........................................7
3.3.2 油脂熱裂解產物與氮化合物反應.........................7
3.4 減少食品中丙烯醯胺生成的方法...........................8
3.4.1 影響丙烯醯胺生成的因子..............................8
3.4.2 降低丙烯醯胺生成的方法..............................8
四、幾丁質與幾丁聚醣......................................9
4.1 幾丁質與幾丁聚醣的分布................................9
4.2 幾丁質與幾丁聚醣的構造...............................10
4.2.1 幾丁質...........................................10
4.2.2 幾丁聚醣..........................................10
4.3 幾丁質與幾丁聚醣的特性...............................11
4.3.1 幾丁質...........................................11
4.3.2 幾丁聚醣..........................................11
4.4 分子量對幾丁聚醣之影響...............................11
4.4.1 抗氧化性..........................................11
4.4.2 抗菌性...........................................12
4.5 幾丁聚醣與梅納反應...................................13
參、實驗架構............................................15
肆、實驗材料與方法.......................................16
一、實驗器材............................................16
1.1 材料...............................................16
1.2 試藥...............................................16
1.3 標準品.............................................17
1.4 菌株...............................................17
1.5 培養基.............................................17
二、儀器設備............................................17
三、實驗方法............................................18
3.1 梅納反應產物製備.....................................18
3.2 梅納反應產物萃取.....................................18
3.3 梅納反應產物之吸光值分析..............................19
3.4 丙烯醯胺含量分析.....................................19
3.5 色差值測定..........................................20
3.6 PH 值測定..........................................20
3.7 黏度測定............................................20
3.8 DPPH自由基清除能力..................................21
3.9 亞鐵離子螯合力......................................21
3.10 還原力............................................21
3.11 梅納反應產物之抗菌性試驗.............................22
3.12 統計分析...........................................22
伍、結果與討論..........................................23
一、褐變產物分析.........................................23
1.1 吸光值.............................................23
1.2 丙烯醯胺含量........................................24
二、物理特性分析.........................................24
2.1 色差值.............................................24
2.2 PH 值..............................................25
2.3 黏度...............................................26
三、抗氧化特性分析.......................................26
3.1 DPPH 自由基清除能力.................................26
3.2亞鐵離子螯合能力......................................27
3.3還原力..............................................27
四、各項參數之相關性分析..................................28
4.1 吸光值與色差值相關性分析..............................28
4.2 吸光值與丙烯醯胺含量相關性分析........................28
4.3 色差值與丙烯醯胺含量相關性分析........................29
4.4 吸光值與抗氧化力相關性分析............................29
4.5 色差值與抗氧化力相關性分析............................30
4.6 丙烯醯胺含量與抗氧化力相關性分析......................30
五、抑菌能力檢測.........................................31
陸、結論................................................32
柒、參考文獻............................................33
捌、圖表................................................45
玖、附錄................................................65





圖目次
圖一、果糖、天門冬醯胺酸及幾丁聚醣之梅納反應產物溶液於 294 nm (A) 及 420 nm (B) 下之吸光值測定結果。...................45
圖二、丙烯醯胺高效能液相層析圖譜。.........................46
圖三、丙烯醯胺濃度標準曲線。..............................47
圖四、果糖、天門冬醯胺酸及幾丁聚醣之梅納反應產物溶液中丙烯醯胺含量。...................................................48
圖五、果糖、天門冬醯胺酸及幾丁聚醣之梅納反應產物溶液外觀顏色。 .......................................................49
圖六、果糖、天門冬醯胺酸及幾丁聚醣混合溶液 pH 值：(A) 各組溶液反應前與反應後 pH 值比較；(B) 各組溶液反應後 pH 值比較。....50
圖七、果糖、天門冬醯胺酸及幾丁聚醣梅納反應產物溶液之運動黏度。 .......................................................51
圖八、果糖、天門冬醯胺酸及幾丁聚醣之梅納反應產物溶液抗氧化特性分析。...................................................52
圖九、吸光值 (OD294 及 OD420) 與色差值 (CIE L*、a* 及 b*) 之線性回歸分析。..........................................54
圖十、吸光值 (OD294 及 OD420) 與丙烯醯胺含量之線性回歸分析。 .......................................................56
圖十一、色差值 (CIE L*、a* 及 b*) 與丙烯醯胺含量之線性回歸分析。...................................................57
圖十二、吸光值 (OD294 及 OD420) 與抗氧化力 (DPPH 自由基清除能力、亞鐵離子螯合能力及還原力) 之線性回歸分析。..............58
圖十三、色差值 (CIE L*、a* 及 b*) 與抗氧化力 (DPPH 自由基清除能力、亞鐵離子螯合能力及還原力) 之線性回歸分析。............60
圖十四、丙烯醯胺含量與抗氧化力 (DPPH 自由基清除能力、亞鐵離子螯合能力及還原力) 之線性回歸分析。..........................61





表目次
表一、果糖、天門冬醯胺酸及幾丁聚醣之梅納反應產物溶液色差值。..62
表二、果糖、天門冬醯胺酸及幾丁聚醣之梅納反應產物溶液對於 Escherichia coli BCRC 10695 及 Bacillus cereus BCRC 10603 之抑菌環直徑。..........................................63
表三、果糖、天門冬醯胺酸及幾丁聚醣梅納反應產物溶液之吸光值、色差值、丙烯醯胺含量及抗氧化力相關係數。.......................64





附錄
附圖一、梅納反應流程。...................................65
附圖二、阿馬多利重排作用。................................66
附圖三、梅納反應之中期與後期反應。.........................67
附圖四、丙烯醯胺結構圖。..................................68
附圖五、食品中丙烯醯胺形成途徑。..........................69
附圖六、葡萄糖─天門冬醯胺酸混合物形成丙烯醯胺及添加金屬離子後反應途徑。................................................70
附圖七、幾丁質的化學結構。................................71
附圖八、幾丁聚醣的化學結構。..............................72

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