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研究生:胡博淳
研究生(外文):Hu Po-Chun
論文名稱:以模式系統探討核黃素及脂肪酸甲酯對膽固醇光氧化的影響
論文名稱(外文):Influence of Riboflavin and Fatty Acid Methyl Esters on Cholesterol Photoxidation in Model Systems
指導教授:陳炳輝陳炳輝引用關係
指導教授(外文):B. H. Chen
學位類別:碩士
校院名稱:輔仁大學
系所名稱:食品營養學系
學門:醫藥衛生學門
學類:營養學類
論文種類:學術論文
論文出版年:2001
畢業學年度:89
語文別:中文
論文頁數:203
中文關鍵詞:膽固醇核黃素脂肪酸甲酯光氧化
外文關鍵詞:cholesterolriboflavinfatty acid methyl esterphotoxidation
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膽固醇普遍的存在於動物性脂肪與奶、蛋類食品中,此類食品經過加熱、儲存或是光照後,其中的膽固醇會進行自氧化或是光氧化反應而形成膽固醇氧化產物(cholesterol oxide products; COPs),這些氧化產物已被證實對人體有不良影響。本研究目的在於探討(1)光敏感劑對膽固醇光氧化的影響;(2)脂肪酸甲酯對膽固醇光氧化的影響;(3)光敏感劑及脂肪酸甲酯共存時對膽固醇光氧化的影響。
模式系統使用的光敏感劑為核黃素(riboflavin),以硬脂酸甲酯(stearic acid methyl ester)、亞麻油酸甲酯(linoleic acid methyl ester)及二十二碳六稀酸甲酯(cis-4, 7, 10, 13, 16, 19-docosahexaenoic acid methyl ester)進行試驗,利用恆溫式旋轉光照設備在照度2000~3000Lux和25℃下進行光照實驗。模式系統中的核黃素及脂肪酸甲酯經過光照後皆會發生裂解,避光儲存則相當安定;核黃素經光照1天即完全裂解;核黃素的添加會加速脂肪酸甲酯裂解,且符合一次反應,三種脂肪酸甲酯於光照過程的安定性以硬脂酸甲酯最佳,其次為亞麻油酸甲酯及二十二碳六烯酸甲酯。
模式系統中的膽固醇經光照後會發生氧化反應形成過氧化產物及COPs,膽固醇的裂解符合一次反應,避光儲存條件下則未發生氧化。核黃素及脂肪酸甲酯的添加皆會增加膽固醇光照後的損失百分比及膽固醇過氧化物生成量,且核黃素對損失百分比及過氧化物生成量的影響程度大於脂肪酸甲酯。模式系統中膽固醇光照後生成的COPs包括7α-OH、7β-OH、7-keto、3,5-cholestadien-7-one、5,6α-EP及5,6β-EP,其中以7-keto、5,6α-EP、5,6β-EP三種COPs的生成量為最多;核黃素及脂肪酸甲酯的添加皆會促進COPs的生成,且核黃素對COPs生成的影響大於脂肪酸甲酯。添加脂肪酸甲酯的組別COPs的生成隨著光照天數呈現線性增加的趨勢,而添加核黃素的組別COPs的生成在反應初期呈現線性增加,反應後期則有平緩或下降的趨勢。在COPs生成的種類方面,核黃素的存在會促使7-keto脫水形成3,5-cholestadien-7-one,而添加二十二碳六烯酸甲酯則會導致膽固醇趨向形成5,6 —EP。

Cholesterol is widely distributed in animal fats, eggs, and dairy products, as well as are susceptible to oxidation to form cholesterol oxidation products (COPs) during heating and illumination. Numerous studies have indicated that COPs may impart potential hazard to health. The purposes of this investigation were: (1) to study the influence of photosensitizer on cholesterol photoxidation, (2) to study the influence of fatty acid methyl esters on cholesterol photoxidation, and (3) to study the influence of combination of photosensitizer with fatty acid methyl esters on cholesterol photoxidation.
Riboflavin was used as the photosensitizer in model systems, together with stearic acid methyl ester, linileic acid methyl ester, and docasahexaenoic acid methyl ester. Samples were illuminated at 2000~3000 Lux and 25℃ in a rolling apparatus. Both riboflavin and fatty acid methyl esters were degraded during light storage, while during dark storage, both showed high stability, and the addition of riboflavin would facilitate degradation of fatty acid methyl esters. The degradation fits a first-order model. Stearic acid methyl ester showed the highest stability during illumination, followed by linoleic acid methyl ester and docasahexaenoic acid methyl ester.
Both cholesterol hyperoxides and COPs were formed during illumination, however, both were not detected during dark storage. The addition of both riboflavin and fatty acid methyl eaters would increase loss percentage of cholesterol and formation of cholesterol hyperoxides, with the former being more effective. The COPs formed during light storage include 7α-OH、7β-OH、7-keto、3,5-cholestadien-7-one、5,6α-EP and 5,6β-EP, of which 7-keto, 5,6β-EP, and 5,6α-EP were present in a large amount. The presence of riboflavin and fatty acid methyl esters would facilitate the COPs production, and the former was more effective than the later. COPs increased linearly with increasing illumination in the initial period; for riboflavin, the levels of COPs formed linearly in the initial period then declined afterwards. The presence of riboflavin also caused dehydration of 7-keto to form 3,5-cholestadien-7-one. In the presence of docasahexaenoic acid methyl ester, the formation of 5,6-EP was favored.

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、膽固醇氧化機制---------------------------------12
(一)自氧化反應--------------------------------12
(1)A、B環自氧化反應----------------15
(2)側鏈自氧化反應--------------------17
(二)光氧化反應--------------------------------18
四、影響膽固醇氧化的因子-------------------------18
(一)溫度---------------------------------------18
(1)膽固醇標準品------------------------20
(2)蛋及蛋製品---------------------------23
(3)乳製品---------------------------------26
(4)魚及魚製品---------------------------27
(5)肉及肉製品--------------------------27
(6)脂質-----------------------------------29
(二)儲藏的條件------------------------------30
(三)酸鹼值-------------------------------------33
(四)光源----------------------------------------34
(五)食品的成分-------------------------------39
(1)膽固醇---------------------------------39
(2)油脂------------------------------------43
(3)鹽---------------------------------------46
(4)胺基酸---------------------------------46
(5)抗氧化劑------------------------------48
(6)β-胡蘿蔔素--------------------------53
(7)磷脂質---------------------------------55
(六)氧源------------------------------------------55
五、膽固醇氧化物對生理的影響------------------58
(一)抑制酵素活性----------------------------58
(二)細胞毒性----------------------------------61
(三)心血管疾病-------------------------------61
(四)致突變性與致癌性----------------------63
六、膽固醇氧化物的萃取、定性與定量分析-----65
(一)分離及純化--------------------------------66
(1)皂化法---------------------------------66
(2)管柱萃取法---------------------------68
(3)酵素萃取法---------------------------69
(4)交酯化萃取法------------------------69
(二)定量及定性分析---------------------------69
(1)薄層層析法--------------------------69
(2)高效率液相層析法-----------------70
(3)氣相層析法---------------------------71
七、核黃素---------------------------------------------73
(一)核黃素簡介---------------------------------73
(二)核黃素之光化學反應---------------------75
(三)核黃素的分析法---------------------------77
八、油脂的氧化反應---------------------------------78
(一)自氧化反應----------------------------------78
(二)光氧化反應---------------------------------80
第三章 材料與方法---------------------------------------82
一、實驗架構------------------------------------------82
(一)核黃素對膽固醇光氧化的影響--------82
(二)脂肪酸甲酯對膽固醇光氧化的影響-83(三)核黃素及脂肪酸甲酯共存對膽固醇光氧化的影響---------------------------------------84
二、試驗材料與設備---------------------------------85
(一)化學藥品-----------------------------------85
(1)膽固醇及膽固醇氧化物標準品-------85
(2)脂肪酸甲酯標準品----------------------85
(3)光敏感劑----------------------------------86
(4)膽固醇衍生化試劑----------------------86
(5)溶劑及其他試藥-------------------------86
(二)儀器設備----------------------------------87
(1)氣相層析儀(GC)-----------------87
(2)氣相層析質譜儀(GC-MS)------87
(3)毛細管柱----------------------------87
(4)高效率液相層析儀(HPLC)-----87
(5)HPLC管柱--------------------------87
(6)恆溫箱-------------------------------88
(7)分光光度計-------------------------88
(8)照度計-------------------------------88
(9)日光燈管----------------------------88
(10)光照設備----------------------------88
三、實驗方法---------------------------------------89
(一)核黃素對膽固醇光氧化的影響-----89
(1)光照試驗----------------------------89
(2)儲存試驗----------------------------90
(3)核黃素的殘留量測定-------------91
1.高效率液相層析(HPLC)-------91
2.核黃素標準曲線的建立---------91
(4)氣相層析質譜儀(GC/MS)分析膽固醇及COPs---------------------92
1.COPs衍生化反應------------------92
2. GC/MS分析條件------------------92
(5)膽固醇氧化產物的定量與膽固醇殘留量的測定----------------------93
1.RF(response factor)值的測定--93
2.膽固醇氧化物的定量------------93
3.膽固醇的殘留量的測定---------93
4.膽固醇裂解速率常數------------94
(6)膽固醇氧化物的鑑定---------------95
(7)膽固醇過氧化物的分析------------95
(二)脂肪酸甲酯對膽固醇光氧化的影響--------------------------------------------96
(1)光照試驗----------------------------96
(2)儲存試驗----------------------------97
(3)脂肪酸甲酯殘留量的測定-------97
1.氣相層析質譜儀分析的條件---97
2.脂肪酸甲酯殘留量---------------97
(4)氣相層析分析COPs-------------------98
(5)膽固醇氧化物的定量與膽固醇的殘留量的測定-----------------------------98
(6)膽固醇氧化物的鑑定-----------------98
(7)膽固醇過氧化物的分析-------------98
(三)核黃素及脂肪酸甲酯共存對膽固醇光氧
化的影響--------------------------------------98
(1)光照試驗--------------------------------98
(2)儲存試驗--------------------------------99
(3)核黃素的殘留量測定-----------------99
(4)脂肪酸甲酯的殘留量測定-----------99
(5)氣相層析分析COPs-------------------99
(6)膽固醇氧化物的定量與膽固醇的殘留量的測定-----------------------------99
(7)膽固醇氧化物的鑑定---------------100
(8)膽固醇過氧化物的分析------------100
(四)統計分析--------------------------------100
第四章 結果與討論--------------------------------------101
一、模式系統開發與分析方法評估--------------------101
(一)模式系統之設計--------------------------------101
(二)模式系統光敏感劑及脂肪酸甲酯之選擇--102
(三)模式系統光照設備的開發--------------------103
(四)GC-MS分析條件之探討----------------------106
(五)內部標準品之選擇-----------------------------110
(六)COPs衍生化之探討---------------------------112
二、光照及儲存對核黃素、脂肪酸甲酯與膽固醇的影響-------------------------------------------------------117
(一)光照及儲存對核黃素的影響---------------117
(1)核黃素之分析方法------------------------117
(2)光照及儲存對核黃素的影響-------------117
(二)光照及儲存對脂肪酸甲酯的影響---------121
(1)光照對脂肪酸甲酯的影響---------------121
(2)避光儲存對脂肪酸甲酯的影響---------126
(三)光照及儲存對膽固醇含量的影響-----------128
(1)添加脂肪酸甲酯光照對膽固醇裂解的影響--------------------------------------------------128
(2)添加核黃素光照對膽固醇裂解的影響-131(3)同時添加脂肪酸甲酯及核黃素光照對膽固醇裂解的影響--------------------------------------133(4)避光儲存對膽固醇的影響-----------------135
三、模式系統中膽固醇光氧化物探討-----------------138
(一)膽固醇過氧化物--------------------------------138
(1)膽固醇過氧化物的分析--------------------138(2)膽固醇總過氧化物的生成-----------------139
(二)膽固醇氧化產物--------------------------------143
(1)模式系統膽固醇氧化產物的種類--------143(2)模式系統中各處理組COPs的生成------145(3)模式系統不同處理條件對7α-OH及7β-OH生成的影響-----------------------------------158(4)模式系統不同處理條件對7-keto生成的影響-----------------------------------------------------162(5)模式系統不同處理條件對5,6α-EP及5,6β-EP生成的影響---------------------------------164(6)模式系統不同處理條件對3,5-cholestadien -7-one生成的影響---------------------------------168(7)膽固醇氧化產物總生成量-----------------170
第五章 結論-----------------------------------------------173
參考文獻---------------------------------------------------175
附錄---------------------------------------------------------198

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