魚油中富含ω-3 多元不飽和脂肪酸，其中又以二十碳五烯酸(eicosapentaenoic acid, 20:5, EPA) 及二十二碳六烯酸 (docosahexaenoic acid, 22:6, DHA) 含量最為豐富，且具有多種生物活性，但他們極易氧化，限制了在食品上的應用。本研究目的在於開發同步奈米膠囊化魚油及槲皮酮，並研究其熱安定性及氧化裂解動力學。利用動態光散射分析儀測定單層、雙層及多層包覆之奈米膠囊之直徑分別為5.94、9.59及10.77nm，其中以多層膠體包覆之奈米膠囊安定性較高。以多層膠體同步包覆魚油及槲皮酮製得奈米膠囊，EPA及DHA的包覆率分別為87.8%及88.5%。在pH 3.5、6.0及6.8下靜置0-4小時奈米膠囊仍穩定，粒徑大小沒有顯著差異且沒有出現聚集現象。但於pH 7.4時，奈米膠囊粒徑顯著變小並有大顆粒聚集的現象。以示差掃描熱分析儀測其熱穩定性，奈米膠囊在pH 3.5及6.0時熱穩定性高達130℃，但在pH 6.8及7.4時有不穩定之熱轉換現象；又將奈米膠囊在pH 6，70℃下加熱2小時依然可維持其為安定狀態。以魚油標準品 (fish oil standard, FO) 作為對照組，將奈米膠囊化魚油 (nano-encapsulated fish oil, NP) 及同步奈米膠囊化魚油及槲皮酮 (simultaneous nano-encapsulated fish oil and quercetin, NPQ)，於70℃下通氮氣加熱，由動力學研究發現熱裂解及異構化速率常數 (k1) 依序為：FO＞NP＞NPQ。FO中EPA及DHA的熱裂解與異構化速率分別為NP及NPQ的1.93-3.12及2.25-2.99倍，顯示槲皮酮及奈米膠囊化均有保護魚油中EPA及DHA免於受熱裂解與異構化的效果。而在70℃通氧加熱時，僅以奈米膠囊化保護魚油中EPA及DHA效果並不好，但含槲皮酮之奈米膠囊對於保護EPA及DHA免於氧化裂解的效果顯著，FO中EPA及DHA的氧化裂解速率分別為為NPQ的42.45及5.67倍，顯示奈米膠囊壁上額外添加槲皮酮可有效的抑制魚油中EPA及DHA之氧化裂解。不論是線性或非線性迴歸分析之相關係數，除了通氮加熱NPQ的相關係數(0.851)較低外，其他皆在0.925以上，顯示本研究推導之動力學方程式可準確估計EPA及DHA熱及氧化裂解濃度變化情形。

Fish oils are rich in ω-3 polyunsaturated fatty acids (ω-3 PUFA). Both especially eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are predominant in ω-3 PUFA and possess many biological activities. However, their food application is limited because of their high susceptibility to oxidation. The objectives of this study are to develop nanoparticles with simultaneous nano-encapsulation of fish oil and quercetin and to evaluate the thermal stability and the oxidative degradation kinetics. Dynamic light scattering analysis showed that the average particle diameters were, respectively, 5.94, 9.59 and 10.77nm for single-, double- and multiple-coating nanoparticles. Among these, multiple-coating nanoparticles had the highest stability. The encapsulation percentage of EPA and DHA in nanoparticles was 87.8% and 88.5%, respectively. The mean diameters of nanoparticles with 0-4 h holding duration were not significantly different at pH 3.5, 6.0 and 6.8. However, aggregation of nanoparticles at pH 7.4 were observed and the particle size was significantly separated into small and large fractions. Results of differential scanning calorimetry indicated that nanopaticles had the thermal stability up to 130℃at both pH 3.5 and 6.0. On the other hand, nanoparticles were unstable at pH 6.8 and 7.4. Nanoparticles maintained its stability during heating at 70℃and pH 6.0 for 2 h. When nano-encapsulated fish oil (NP) and simultaneous nano-encapsulaed fish oil and quercetin (NPQ) were heated with nitrogen purging at 70℃with using fish oil (FO) as a contrast, the rate constants of thermal degradation and isomerization (k1) were observed as follows: FO>NP>NPQ. The rate constants k1 of EPA and DHA in FO were, respectively, found to be 1.93-3.12 and 2.25-2.99 times higher than those in NP and NPQ, denoting that quercetin and nano-encapsulation could effectively reduce the reaction rates of thermal degradation and isomerization. When NP and NPQ were heated with oxygen purging, the inhibition of oxidative degradation for EPA and DHA in NP were insignificant. The oxidative degradation rate constants (k2) of EPA and DHA in NPQ were greatly reduced by 42.45 and 5.67 folds as compared with those of FO, depicting that extra coating of quercetin on the outmost layer of nanoparticles could effectively inhibit the oxidative degradation. For various reaction constants analyzed by linear and nonlinear regressions, all the correlation coefficients were higher than 0.925, expect for the heating of NPQ with nitrogen purging (r2 = 0.851). The kinetic models developed in this study can be used to predict the concentration changes of thermal and oxidative degradation of both EPA and DHA in nanoparticles.

目錄
頁次
第ㄧ章、緒言 1
第二章、文獻回顧 3
一、ω-3多元不飽和脂肪酸 3
 (一) ω-3多元不飽和脂肪酸簡介 3
 (二) ω-3多元不飽和脂肪酸氧化機制 6
(三) ω-3多元不飽和脂肪酸分析方法 11
二、類黃酮物質 15
(一) 類黃酮物質簡介 15
(二) 類黃酮物質抗氧化性 20
(三) 槲皮酮的抗氧化機制 22
三、微膠囊化 24
(一) 微膠囊化簡介 24
(二) 多層膠囊之效用 27
(三) 微膠囊之應用 28
四、奈米化之功用 32
第三章、材料與方法 36
ㄧ、實驗材料 36
二、儀器設備 37
三、實驗架構 39
四、樣品製備 40
(一) 動物膠之鹼處理 40
(二) 紅藻膠之處理 40
(三) 奈米膠囊之製備 40
五、分析方法 41
(一) 以氣相層析法分析魚油中脂肪酸 41
(1) 衍生化方法 41
(2) 脂肪酸之分析方法 41
(3) EPA及DHA脂肪酸之定量 42
(二) 以高效液相層析法分析槲皮酮 42
(1) 分析條件 42
(2) 定量方法 43
(三) 粒徑分析 43
(四) 奈米膠囊中EPA及DHA之包覆率分析 43
(五) 示差掃描熱分析 44
(六) 熱及氧化裂解速率分析 44
六、統計分析 45
第四章、結果與討論 46
一、奈米膠囊之包覆壁膠體 47
(一) 膠體複合物之交互作用 47
(二) 包覆層對奈米膠囊粒徑分佈之影響 51
二、奈米膠囊安定性之分析 54
(一) 粒徑分析 54
(1) pH值之影響 54
(2) 靜置時間之影響 57
(二) 熱安定性 62
三、奈米膠囊化魚油之氧化安定性 64
(一) 魚油中脂肪酸之分析 64
(二) 奈米膠囊中魚油之包覆率 66
(三) PUFA之熱裂解及氧化動力學分析 68
(1) 異構化及熱裂解 72
(2) 氧化裂解 76
第五章、結論 81
第六章、參考文獻 82

圖目錄
頁次
圖一、多元不飽和脂肪酸與花生四烯酸合成促發炎物質類二十碳酸的
交互作用 7
圖二、利用氣相層析法分離鯖魚脂肪酸甲基酯化物 14
圖三、類黃酮基本結構 18
圖四、類黃酮主要分類與結構 19
圖五、槲皮酮結構圖 23
圖六、類黃酮具有高抗氧化力的官能基 23
圖七、由槲皮酮及morin中分離的酚酸 25
圖八、ㄧ級與二級乳化系統之粒徑對pH之依賴性 29
圖九、ㄧ級與二級乳化系統粒徑對食鹽濃度之依賴性 30
圖十、複合膠體之示差掃描熱分析圖 50
圖十一、包覆層對奈米膠囊粒徑分佈之影響 52
圖十二、pH對奈米膠囊粒徑分佈之影響 55
圖十三、pH 3.5靜置時間對奈米膠囊粒徑分佈之影響 58
圖十四、pH6.0靜置時間對奈米膠囊粒徑分佈之影響 59
圖十五、pH 6.8靜置時間對奈米膠囊粒徑分佈之影響 61
圖十六、pH對奈米膠囊在25mM磷酸緩衝溶液中熱安定性之影響
63
圖十七、加熱時間對奈米膠囊粒徑分佈之影響 65
圖十八、魚油中脂肪酸之氣相層析圖 67
圖十九、魚油於充氮或氧氣加熱時之裂解、異構化及氧化途徑 71
圖二十、奈米膠囊化魚油中EPA及DHA在充氮氣70℃加熱時之
殘存量變化 75
圖二十一、奈米膠囊化魚油中EPA及DHA在充氧氣70℃加熱時之
殘存量變化 79


表目錄
頁次
表一、長鏈不飽和脂肪酸之組成份 4
表二、鯖魚中主要脂肪酸經快速氧化測試的含量 13
表三、食物中類黃酮來源及含量 17
表四、評估化合物抗氧化能力之參數 26
表五、添加經加熱後的槲皮酮及5-CQA對大豆油中測其氧化安定性
26
表六、魚油及奈米膠囊中EPA及DHA之熱及氧化裂解反應速率常數
與相關係數 74

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