臺灣博碩士論文加值系統

本研究主要探討食用油脂加熱至發煙點所生成油煙的安全性，並針對花生油油煙的致突變性與其主要致突變物進行鑑定，且對其導致人類細胞基因毒性與可能機制加以探討，並進一步將花生油進行脫膠處理與添加抗氧化劑，以期達到降低其加熱油煙致突變性的目的。
首先以市售大豆油、玉米胚芽油、葵花油、花生油、調合花生油、芥花油和豬脂為材料，探討油脂之理化性質，並以安氏試驗法 (Ames test)測定在發煙點溫度產生之油煙的毒性與致突變性。結果顯示七種油脂之發煙點依序為118、119、95、98、107、138 及 137 oC；其中以豬脂之氧化安定性最佳，花生油次之；油煙量則以花生油生成最多。各種食用油脂之油煙對Salmonella typhimurium TA98與TA100 均具有不同程度之致突變性。
由於花生油向有易起油煙之害，且為省產主要食用油脂，因此繼續探討花生油油煙致突變成分之研究。結果顯示花生仁經焙炒後所製得之花生油的發煙點溫度與不飽和脂肪酸含量較花生仁未經焙炒所製得之花生油為低且顏色較深，所產生之油煙量與致突變性均較高。油煙甲醇萃取物的中性區分物之致突變性最強，以GC/MS分析其組成發現共含1-pentanol等12種化合物。在這些成分中具致突變性之成分有trans-trans-2,4-decadienal (t-t-2,4-DDE)、trans-trans-2,4-
nonadienal (t-t-2,4-NDE)、trans-2-decenal (t-2-DCA)及trans-
2-undecenal (t-2-UDA)。對TA98 與TA100致突變性的強弱順序
分別為t-t-2,4-DDE > t-t-2,4-NDE > t-2-DCA > t-2-UDA。
以人類A-549細胞株 (human lung carcinoma pulmonary typeⅡ-like epithelial cell)為對象，繼續探討花生油煙之細胞毒性與基因毒性，同時探討主要致突變成分t-t-2,4-DDE誘導活性氧生成之效應。結果顯示油煙甲醇萃取物可造成明顯之細胞毒性與DNA氧化傷害，並降低細胞內glutathione (GSH)的含量與GSH 抗氧化酵素之活性。t-t-2,4-DDE 於37 oC，pH 7.4之磷酸緩衝溶液中具有生成超氧因離子、過氧化氫及氫氧自由基等活性氧的能力。且隨添加劑量與反應時間的增加，對細胞胞內活性氧的生成量亦隨之增加，且對細胞DNA的2’-deoxyguanosine具有顯著性氧化生成8-hydroxy-2’-deoxyguanosine
(8-OHdG)的能力。由此結果，油煙所導致A-549 細胞的DNA損傷與其主要致突變成分t-t-2,4-DDE的生成ROS有密切關係。
花生油經脫膠處理後，探討對其加熱油煙的致突變性與致突變物含量之影響。花生油經脫膠處理後，油色較為澄清透明，其發煙點顯著提高。產生之油煙量與油煙對TA98與TA100之致突變性可分別降低81與73%。各種脫膠條件中以溫度60℃、加水量3％之效果最佳。此處理可使油煙中之t-t-2,4-DDE、t-t-2,4-NDE、t-2-DCA及t-2-UDA等四種致突變物含量顯著降低。花生油中游離脂肪酸 (free fatty acid; FFA)含量與其加熱油煙的致突變性的相關性高達r2 =0.9978; FFA與油煙中t-t-2,4-DDE含量的相關性為r2 =0.7685;而油煙的致突變性與油煙中t-t-2,4-DDE含量的相關性也達 r2 = 0.7816，顯示油煙的致突變性與油中游離脂肪酸及其加熱油煙中
t-t-2,4-DDE含量有密切關聯性。
於脫膠花生油中添加抗氧化劑，探討對其油煙致突變物生成之影響。結果顯示，butylated hydroxyanisole (BHA)、butylated hydroxytoluene (BHT)、tertiary butylhydroquinone (TBHQ)、-tocopherol、catechin 及rosemary extracts等抗氧化劑添加於脫膠花生油中，均能降低其加熱油煙之致突變性及減少油煙中t-t-2,4-DDE、t-t-2,4-NDE、t-2-DCA及t-2-UDA等致突變物
的含量。抗氧化劑之添加亦能提高花生油之發煙點、氧化安定性及減少加熱油煙的產率，其中以BHA、
BHT與TBHQ等抗氧化劑的效果較為顯著。因此於油中添加適當的抗氧化劑，不僅能減低其加熱油煙中致突變物的生成，也有助於改善油脂之理化性質。由此結果，可作為日後開發高發煙點、低油煙產率與低致突變性食用油脂的
參考。
由上述研究結果得知，花生油經加熱至發煙點時所產生的油煙對細胞具有致突變性與基因毒性。經區分可鑑定出t-t-2,4-DDE、t-t-2,4-NDE、t-2-DCA及t-2-UDA等四種致突變物。油煙生成活性氧為導致胞內DNA 的斷裂與鹼基突變之主因。將花生油經脫膠處理及添加抗氧化劑後可改善油品理化特性，並降低油煙致突變物之生成量，具有
降低烹調油煙對婦女健康危害之潛力。

The aim of this study is to investigate the safety of oil fume produced from peanut oil heated to its smoke point. The mutagenicity, genotoxicity and possible mechanisms of the oil fume were evaluated, and mutagens present in oil fumes were identified. The peanut oil was then refined and treated with addition of antioxidants in order to reduce the mutagenicity of the oil fumes from heated oil.
The first part of this study focuses on investigation of the Seven commercial edible oils including soybean oil, corn germ oil, sunflower oil, peanut oil, blend peanut oil, calola oil and lard were investigated for their physical and chemical properties as well as for the mutagenicity of oil fumes by applying the Ames test. The smoke points of those oils were 118, 119, 95, 98, 107, 138 and 137 oC, respectively. Lard had the best oxidative stability among those seven oils as determined by the Rancimat method. Peanut oil produced the largest amount of fume. The oil fumes of these edible oils showed various degrees of mutagenicity toward Salmonella
typhimurium TA98 and TA100 (p<0.05).
According to the undesirable fumes formation of peanut oil at relatively low temperature, which is the major edible oilproduced in Taiwan. The mutagenicity of fumes obtained from heating peanut oil was studied and the mutagenic compounds was identified. The result revealed that the peanut prepared from roasted peanut kernel (ROPO) showed a lower smoke point, less unsaturated fatty acids, more fume formation and stronger mutagenicity than that from unroasted kernel (UROPO). Further investigation of mutagenic compounds was performed by the Ames test and GC/MS analysis. Amoung the twelve compounds identified from the neutral fraction of methanol extract four compounds at a dose of 10 g per plate were mutagenic to Salmonella TA98 and TA100 cells in the order trans-trans-2,4-decadienal (t-t-2,4-DDE) >trans-trans-
2,4-nonadienal (t-t-2,4-NDE) >trans-2-decenal (t-2-DCA) >trans-2-undecenal (t-2-UDA). Results report the enal compounds formed as the mutagens in the fumes of peanut oil and indicate that inhaling cooking fumes might cause
carcinogenic risk.
The cytotoxicity of peanut oil fumes (POF) and their genotoxicity using single-cell electrophoresis (comet assay), and their induction of reactive oxygen species (ROS) in human A-549 cells were investigated. POF was found to show cytotoxicity to A-549 cells and DNA damage. The glutathione (GSH) content in cell and the activity of GSH antioxidative enzymes were reduced. t-t-2,4-DDE at 37 oC could produce superoxide anion, hydrogen peroxide, and hydroxyl radicals in phosphate buffer (pH 7.4), and form intracellular reactive oxygen species (ROS) in A-549 cells which was determined by dichlorofluorescein assay. Moreover, t-t-2,4-DDE caused a significant (p<0.05) oxidative damage of 8-hydroxy-2’
deoxyguanosine (8-OHdG)to 2’-deoxyguanosine in A-549 cells. While increasing damage of t-t-2,4-DDE and reaction time, the results demonstrated that the DNA damage in A-549 cells induced by t-t-2,4-DDE was related
to the formation of ROS.
The influence of degumming treatment of peanut oil on the contents of mutagenic compounds in fumes from heated peanut oil was investigated. The results indicated that the peanut oil prepared from roasted peanut kernels underwent degumming treatment had lower free fatty acid (FFA) content and higher smoke point, was more clear in color, and produced less fumes when heated at smoke point. Moreover, when compared to untreated peanut oil, the mutagenicity of oil fumes of degummed peanut oil toward Salmonella typhimurium TA98 and TA100 was reduced to 81 and 73% (p<0.05), respectively. The degummed peanut oil which was obtained by adding 3% water and heating at 60℃ for 20 min produced the least amount of mutagenic fume. The contents of four mutagenic compounds, t-t-2,4-DDE, t-t-2,4-NDE, t-2-DCA,and t-2-UDA in oil fumes of
degummed peanut oils were drastically decreased (p<0.05), especially the t-t-2,4-DDE. The results also indicated that FFA content had a high linear correlation with mutagenicity (r2 = 0.9978) and content of t-t-2,4-DDE (r2 = 0.7685). Moreover, there was a correlation (r2 = 0.7816) between the content and the mutagenicity of t-t-2,4-DDE. The decrease of FFA by degumming might explain the reduction of mutagenic alkenal compounds and mutagenicity of fumes from heated peanut oil.
The preventive effects of various antioxidants on the mutagenicity and the formation of enal mutagenic compounds in degummed peanut oil (DPO) fumes were investigated. The mutagenicity of the DPO fumes was significantly reduced (p< 0.05) by various antioxidants added before heating. The addition of antioxidants increase the smoke point and oxidative stability of DPO, and decreased the yield of oil fumes and the amount of mutagens. Synthetic antioxidants including butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and
tertiary butylhydroquinone (TBHQ) were more
effective in reducing the mutagenicity and the amount of four enal compounds in fumes from DPO than natural antioxidants such as -tocopherol, catechin, and rosemary extracts. Adding appropriate antioxidants not only reduced the mutagens but also improved the physical and chemical properties of DPO. The results obtained in this study might be useful for developing edible cooking oils with high smoke point, lesser fume, and lower mutagenicity
with the addition of antioxidants.
In this study, the oil fumes from heated oil were found to be mutagenic and genotoxicity. After fractionation, 4 mutagens including t-t-2,4-DDE, t-t-2,4-NDE, t-2-DCA and t-2-UDA were identified. The ROS present in oil fumes could lead to the cleavage of DNA as well as the mutations of base pairs in the DNA. It was found that both the degumming process and the addition of antioxidants could generally improve the physico-chemical properties of peanut oil, reduce the content of all four mutagens present in the oil fumes, and therefore decrease the potential health hazards to household women exposed to the oil fumes.

中文摘要…………………………………………………………………..………….… 1
英文摘要………………………………………………………..……………. 4
前言……………………………………………………………………… 9
研究目的………………………………………………………………… 12
本論文之研究架構…………………………………………….…………… 14
第一章 文獻整理………………………….………………..…..………..… 19
第二章 數種市售食用油脂的理化特性與油煙致突變性…….…… 36
摘要…………………………………………………………………...…. 37
前言………….……..……………………………………………………… 38
材料與方法……………………………………………………..………… 39
結果與討論…………………………………………………………..… 43
一、七種食用油脂的理化性質……………………………………… 43
二、七種食用油脂的油煙產率與氧化安定性……………………… 44
三、七種食用油脂之油煙毒性與致突變性………………………… 44
第三章 花生油油煙致突變性之研究………………………………… 55
摘要….………………………………………………………………………… 56
前言..………………………………………………………………………… 57
材料與方法.………………………………………………………………… 59
結果與討論………………………………………………………………… 66
一、花生油之理化性質…………………………………………… 66
二、花生油油煙萃取率………………………………………………… 66
三、花生油煙甲醇萃取物之毒性與致突變性試驗…………… 67
四、酸性、中性與鹼性區分物之致突變性…………….…………… 68
五、花生油煙甲醇萃取物中性區分物之鑑定…………… 68
六、Trans-trans-2,4-decadienal、trans-2-undecenal、
trans-2-decenal及trans-trans-2,4-nonadienal之
致突變性…………………………………………………………
69
第四章 花生油煙對人類肺癌細胞株之氧化傷害………………… 79
摘要………….……………………………………………………………… 80
前言………………………………………………………………………… 81
材料與方法………………………………………………………………. 83
結果與討論……………………………………………………………… 91
一、油煙萃取物對細胞之細胞毒性與基因毒性…………………… 91
二、油煙萃取物對細胞脂質過氧化作用之影響…………………… 92
三、油煙萃取物對細胞內GSH含量與GSH
酵素活性之影響……………………………………….….
92
四、油煙萃取物主要致突變成分t-t-2,4-DDE產生
活性氧之探討………………………………………………….….
94
五、t-t-2,4-DDE對肺癌細胞 (A-549) DNA 氧化
生成8-OHdG之影響……………………………………………… 97
六、t-t-2,4-DDE產生自由基之可能機制………………… 98
第五章 花生油經脫膠處理對其油煙致突變性之影響…………………… 113
摘要………………………………………………………………….…. 114
前言………………………………………………………………………. 115
材料與方法…………………………………………………..…………. 117
結果與討論…………………………………………………..…………. 122
一、脫膠處理對花生油理化性質之影響……….…...……………… 122
二、脫膠花生油之油煙產率…………………………..…….………. 122
三、脫膠花生油油煙之毒性與致突變性…………………………. 123
四、脫膠花生油油煙中trans-trans-2,4- decadienal,
trans-trans-2,4-nonadienal, trans-2-undecenal及trans-2-decenal之致突變物含量…………………………….…
124
五、脫膠花生油之氧化安定性……………………………… 125
第六章 花生油中添加抗氧化劑對其油煙致突變物生成之影響………..… 132
摘要…………………………………………………………….…….… 133
前言…………………………………………………………………….… 134
材料與方法……………………………………………………………… 136
結果與討論……………………………………………………………… 141
一、脫膠花生油添加抗氧化劑對其油煙產率之影響……….. 141
二、脫膠花生油添加抗氧化劑所生成油煙之致突變
性……………………………………………………………
141
三、脫膠花生油添加抗氧化劑對油煙中致突變物
含量之影響……. ………………………………………………
142
四、脫膠花生油添加抗氧化劑對其氧化安定性之
影響….……………………………………………………
143
五、脫膠花生油添加抗氧化劑對其發煙點之影響.…………… 144
總結論……………………………………………………………………………. 152
第七章 參考文獻………………………………………….……………..….. 154

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