臺灣博碩士論文加值系統

摘要

利用蒸氣蒸餾萃取文旦果皮之精油，並以GC-MS分析其成分組成，共鑑定出33個化合物，主要成分為limonene（940.07 mg/g），其次為myrcene（23.65 mg/g），次之為β-pinene（13.53 mg/g）。在自體酵素試驗，文旦果皮於30 oC反應15天，並以水蒸餾法萃取精油，其萃取率明顯的由2.50下降至2.04%，而精油中主要碳氫萜烯類化合物由911.68降低至828.19 mg/g，主要含氧萜烯類化合物由9.46增加至12.43 mg/g。然而利用蒸氣蒸餾萃取，於50 oC反應2天的文旦皮精油，其萃取率亦明顯的由2.48下降至1.64%，精油中主要碳氫萜烯類化合物由原來的982.15減少至864.35 mg/g，而主要含氧萜烯類化合物則由10.95增加至13.92 mg/g。
以未經均質（0 rpm）的精油乳化物（0.1、0.2及0.4%）對S. aureus及E. coli 的抗菌效果皆隨著精油濃度的增加而提高。濃度為0.4%時比控制組分別降低了1.03及0.85 Log CFU/mL。以24000 rpm轉速均質之精油乳化物對S. aureus及E. coli的抑制效果皆高於13500 rpm。然而經24000 rpm均質之精油乳化物對E. coli的抗菌效果比未均質的高，MIC值可由0.49降低至0.25%，明顯提高其抑制E. coli之效果。精油乳化物（0.1、0.2及0.4%）經微射流1次及3次循環處理後，粒徑大小平均分別為1383.5及216.6 nm。然而以0.4%精油乳化物經1次循環處理後對S. aureus之抑制效果最佳，比控制組降低了1.13 Log CFU/mL。以相同濃度之乳化精油經1次及3次循環處理後對E. coli亦具有明顯的抑制效果，且比控制組分別降低了1.12及1.16 Log CFU/mL。且經微射流1次循環處理後可提高低濃度（0.1%）之精油對S. aureus及E. coli 的抗菌效果，比控制組分別下降0.88及1.02 Log CFU/mL。
僅添加水溶性幾丁聚醣（DA=54.8%）的抗菌效果隨著濃度的增加而上升，濃度於500 ppm時，對S. aureus具最佳抑制效果，比控制組降低了1.12 Log CFU/mL。然而水溶性幾丁聚醣濃度為1000 ppm時，E. coli的菌數則比控制組降低了1.07 Log CFU/mL，因此明顯的表示幾丁聚醣對S. aureus的抑制效果高於E. coli。於0.4%的文旦皮精油乳化物（經 24000 rpm均質）中添加不同濃度之幾丁聚醣（100、300、500及1000 ppm）相較於僅含幾丁聚醣及精油乳化物的抗菌效果，對S. aureus及E. coli之抑制效果皆具明顯的增加，分別以300及500 ppm時，比控制組降低了2.40及2.55 Log CFU/mL。在不同pH值時，文旦皮精油乳化物（0.4%）對S. aureus的抑制率則隨著pH值上升而增加，而幾丁聚醣（300 ppm）於pH 5.5下對S. aureus及E. coli 之抑制率高於pH 7.4及8.5。然而在pH 7.4時，將300 ppm之幾丁聚醣添加入0.4%之文旦皮精油乳化物對此兩株菌種皆具最佳的抗菌效果，其抑制率分別為99.48和99.06%。

Abstract

Pummelo peel oil was extracted by steam distilation and the constituents were analyzed by GC-MS. There were thirty-three compounds identified from the essential oil. The main compound was limonene (940.07 mg/g), the second was myrcene (23.65 mg/g), and the third was β-pinene (13.53 mg/g). In order to find the effect of endogenous enzymes on composition of pummelo peel oil, the oil was extracted by water distillation after reacting with endogenous enzymes for 15 days at 30oC. The yield of the essential oil decreased from 2.5 to 2.04%. The amount of hydrocarbon monoterpenes in the essential oil decreased from 911.68 to 828.19 mg/g, while the oxygenated terpenes increased from 9.46 to 12.43 mg/g. If the pummelo peel oil was extracted by steam distillation after reacting with endogenous enzymes for 2 days at 50oC, the yield of the essential oil significantly decreased from 2.48 to 1.64%. The hydrocarbon monoterpenes in the oil decreased from 982.15 to 864.35 mg/g and the oxygenated terpenes increased from 10.95 to 13.92 mg/g.
The antibacterial effect of emulsified pummelo peel oil (without homogenization) on S. aureus and E. coli increased as the concentration of the oil raised. The plate counts of S. aureus and E. coli were lower (1.03 and 0.85 CFU/mL, respectively) than the control when 0.4% essential oil was used. The antibacterial effects of emulsified pummelo peel oil, which had been homogenized at 24000 rpm, on S. aureus and E. coli were higher than that homogenized at 13500 rpm as well as that without homogenization for E. coli. The MIC (minimum inhibitory concentration) value for E. coli decreased from 0.49 to 0.25%. The mean partical size of the emulsified pummelo peel oil was 1383.5 nm after being homogenized with 1 time of microfluidizing treatment. The size decreased to 216.6 nm while the microluidizing treatment increased to 3 times. The inhibitory effect of S. aureus was the best when 0.4% emulsified pummelo peel oil was homogenized with 1 time of microfluidizing treatment, of which the plate count of S. aureus was 1.13 Log CFU/mL lower than the control. The same concentration of emulsified pummelo peel oil also had significant inhibitory effect on E. coli after the essential oil was homogenized with 1 and 3 times of microfluidizing treatments, of which the plate counts of E. coli were respectively 1.12 and 1.16 Log CFU/mL lower than the control. The emulsified pummelo peel oil with lower concentration (0.1%) could increase its inhibitory effects on both S. aureus and E. coli after the essential oil was homogenized with 1 time of microfluidizing treatment, of which the plate counts of S. aureus and E. coli were respectively 0.88 and 1.02 Log CFU/mL lower than the control.
The antibacterial effect raised by adding water-souble chitosan (DA=54.8%) alone when the concentration increased. The inhibitory effect on S. aureus reached to the maximum when the concentration of water-souble chitosan was 500 ppm, of which the plate count of S. aureus was 1.12 Log CFU/mL lower than the control. The plate count of E. coli was only 1.07 Log CFU/mL lower than the control as the concentration of water-souble chitosan increased to 1000 ppm; hence, the water-souble chitosan exhibited higher inhibitory effect on S. aureus than on E. coli. The 0.4% emulsified pummelo peel oil (homogenized at 24000 rpm) adding different concentrations of water-souble chitosan (100, 300, 500 and 1000 ppm) was found to have higher antibacterial effect than both water-souble chitosan and emulsified pummelo peel oil without adding chitosan. The inhibitory effects on S. aureus and E. coli increased significantly when 300 and 500 ppm of water-souble chitosan was added in 0.4% emulsified pummelo peel oil. The plate counts of S. aureus and E. coli were respectively 2.40 and 2.55 Log CFU/mL lower than the control. As for the pH effect, the inhibitory percentage of S. aureus for the 0.4% emulsified pummelo peel oil increased as the values of pH raised. The water-souble chitosan (300 ppm) had higher inhibitory percentage for S. aureus and E. coli at pH 5.5 than at pH 7.4 and 8.5. The 0.4% emulsified pummelo peel oil which had been added with 300 ppm water-souble chitosan showed the best inhibitory effects on both bacteria when the value of pH was 7.4. The inhibitory percentages were 99.48 and 99.06% for S. aureus and E. coli, respectively.

目錄
頁次
中文摘要………………………………………..……………................... i
英文摘要..................................................................................................... iii
目錄………………………………………………..…………….……...... vi
表目錄……………………………………………………….…..……….. xii
圖目錄………………………………………………………...…………. xiv
第一章 前言…...……………………………………………..………….. 1
第二章 文獻整理……...……………………………………...…...…….. 3
（一）麻豆文旦之簡介……………..…………………………………..
3
（二）精油之簡介....………………..………………………………….. 4
（三）精油之萃取方式………….…..…………………….…..……….. 5
1. 水蒸餾法……………..………….……...…………...……..... 5
2. 蒸氣蒸餾法………………………….………………….…… 5
3. 有機溶劑萃取法……..………...……….…………………… 6
4. 同時蒸氣蒸餾—有機溶劑萃取法……….……..….……….. 6
5. 冷吸法……………………..………………….…..….……… 6
6. 壓榨法……………..…………………………........………… 7
7. 超臨界流體萃取法………………..………………....……… 7
（四）精油之化學性質…………………………………………..…….. 8
1. 萜烯類化合物……………………………..…….…..………. 8
2. 文旦皮精油之成分組成……………………………..……… 9
3. limonene之轉換作用…………………………………..…….. 10
3-1. 微生物法…………….…………...................................... 10
3-2. 酵素法………………..……………...…….…….…….... 11
（五）精油抗菌活性之研究………………………..…………..…....... 12
1. 精油之抗菌活性………………………..…..……………….. 12
2. 萜烯類化合物之抗菌活…………..………..………..……… 13
3. 精油之抑菌機制……………………………..………..…….. 14
3-1. 格蘭氏陰性菌…………..………………...………..…… 15
3-2. 格蘭氏陽性菌………..……………………...…..……… 15
（六）精油對昆蟲之抑制…………………………….……..………… 16
1. 精油之抗蟲活性………………………………………..…… 16
2. 萜烯類化合物之抗蟲活性……..…………..…….………..... 17
（七）精油之應用……………………………………..…….……........ 17
1. 食品方面………………………………..……..…….……..... 17
2. 化妝品工業方面……………………..………..…..………… 18
3. 醫藥方面……………………..………..…………………….. 18
4. 其它………………………………..…..…………………….. 18
（八）水溶性幾丁聚醣之製備………………..………………………. 19
1. 酸水解法…………………..…………………..…..………… 19
2. 鹼水解法……………..………………………..….……......... 19
3. 酵素水解法……………..……………………..…..………… 20
4. 物理方法………………………..……………..……..……… 21
5. 化學修飾法……………………………………..…………… 21
（九）水溶性幾丁聚醣之應用……………………………..….……..... 22
1. 食品方面…………….…………………………..……..…..... 22
2. 生物醫學方面…………………………………………..…… 23
3. 工業方面………………………………………….……......... 24
4. 化妝品方面……………………..………………..………..… 24
（十）幾丁聚醣之抑菌機制…………………..……………………..… 25
1. 幾丁聚醣結構上之陽離子對細胞表面上陰電荷的干擾..… 25
2. 幾丁聚醣結合DNA以抑制mRNA的合成………….......... 26
（十一）幾丁聚醣—精油之抗細菌活性………………....................... 27
第三章 材料與方法…………………………...………………………… 28
一、實驗材料……………………………….…..…………………….. 28
（一）樣品………………………………………..…………………….. 28
（二）標準品……………………..………………..…………………… 28
（三）藥品………..….……………………………..……….………….. 28
（四）培養基…………….…………………………..…….…………… 29
（五）菌株……………………………..……………..………………… 29
（六）層析管柱……….…..…………………………..……………....... 29
（七）透析膜………….………….……………………..……..……...... 30
（八）儀器…………….…………..………………………….……........ 30
二、實驗方法………………………………………………………..… 32
（一）文旦果皮精油的萃取與分析………………………….………... 32
1. 樣品前處理…………..………………………….……............ 32
2. 自體酵素之試驗…………………..……..………….……...... 32
3. 蒸氣蒸餾法萃取文旦皮之精油…………..…………..……... 33
4. 水蒸餾法萃取文旦皮之精油………………….……..……… 33
5. 文旦皮精油的成分組成及含量之分析…………..….……… 34
5-1. 精油樣品之定性分析…...……………………………… 34
5-2. 精油標準品之配製……..…………………….………… 34
5-3. 精油樣品之定量分析………...................…….………... 35
（二）水溶性幾丁聚醣之製備及分析………………...…….….…..…. 36
1. 水溶性幾丁聚醣之製備…………...…………..…...……..…. 36
2. 幾丁聚醣乙醯化程度之測定…………………..….…..…..… 36
2-1. 標準品之配製…………………...…………...………..... 36
2-2. 樣品之分析…………………………………..…………. 37
3. 蛋白質含量之測定……………………………….………….. 39
4. 灰分含量之測定………………………………....………....... 39
5. 幾丁聚醣於tryptic soy broth（TSB）中之界面電位分析… 40
（三）文旦皮精油乳化物之製備與分析……………………...……..... 40
1. 不同均質轉速的精油乳化物之製備…………..……...…...... 40
2. 高速微射流處理之精油乳化物…………….………....…….. 41
2-1. 樣品之製備………………………….……...……...…… 41
2-2. 粒徑之分析……………………………...…………...…. 41
（四）文旦皮精油乳化物抗細菌活性之試驗……………………...…. 42
1. 菌種之保存和活化………………………..……..…….…..… 42
2. 抗菌試驗………………………..………………...…….……. 42
2-1. 菌種之培養…………..……………………...………...... 42
2-2. 肉湯稀釋法測其生菌數………..……..…….……….…. 42
2-3. MIC（minimum inhibitory concentration）值之測定….. 43
3. 統計分析…………………...…………………….…….…...... 44
（五）幾丁聚醣添加於文旦皮精油乳化物中抗細菌活性之試驗…… 44
1. 幾丁聚醣濃度之影響………………………………….…….. 44
2. pH之影響……………………………….……………………. 45
第四章 結果與討論………………..….…………………………….…… 46
（一）文旦皮精油之成分組成………………………………………… 46
1. 水蒸餾萃取文旦果皮精油的成分分析…………………....... 46
2. 文旦果皮於30 ℃下自體酵素反應不同時間後以水蒸餾萃取精油中成分變化的影響………………………………...…
47
3. 蒸氣蒸餾萃取文旦果皮精油的成分分析………...……........ 49
4. 文旦果皮於50 ℃自體酵素作用後以蒸氣蒸餾萃取精油中成分變化的影響……………………………………………...
49
5. 水蒸餾法及蒸氣蒸餾法於不同自體酵素反應條件下對文旦皮精油之萃取率的影響…………………………………...
50
（二）文旦皮精油乳化物對S. aureus及E. coli之抗細菌活性的影響………………………………………………………………....
51
1. 濃度之影響…………………………………………………... 51
2. 濃度及均質轉速之影響……………………………..………. 53
3. 濃度及粒徑之影響…………………………………..………. 54
（三）幾丁聚醣添加於文旦皮精油乳化物中對S. aureus 和E. coli之抗細菌活性的影響……………………………………..……..
55
1. 幾丁聚醣濃度之影響………………………..………………. 55
2. pH值之影響……………...………………............................... 57
第五章 結論………………………………………...…….….................... 60
第六章 參考文獻……………………………………..….……................. 61
表……………………………………….…….…..……………................ 82
圖…………………………………………………………………............ 111
附錄A………………………………………………………...…………. 124
附錄B…………………………………………………………...………. 127

























表目錄

表一、水蒸餾萃取文旦皮精油之成分組成………………………… 82
表二、文旦皮於30oC自體酵素反應5天以水蒸餾萃取之精油的成分組成…………………………………………………………
84
表三、文旦皮於30oC自體酵素反應10天以水蒸餾萃取之精油的成分組成………………………………………………………
86
表四、文旦皮於30oC自體酵素反應15天以水蒸餾萃取之精油的成分組成………………………………………………………
88
表五、文旦皮於30oC自體酵素反應20天以水蒸餾萃取之精油的成分組成………………………………………………………
90
表六、文旦皮於30oC自體酵素反應25天以水蒸餾萃取之精油的成分組成………………………………………………………
92
表七、蒸氣蒸餾萃取文旦皮精油之成分組成………………………. 94
表八、文旦皮於50 oC自體酵素反應2天以蒸氣蒸餾萃取之精油的成分組成………………………………………..………………
96
表九、萃取方法與自體酵素反應之條件對文旦皮精油成分（concentration, mg/g）之影響………………………………
98
表十、不同濃度之文旦皮精油乳化物對S. aureus及E. coli生菌數（Log CFU/mL）的影響………………………………………
99
表十一、不同均質轉速及濃度之文旦皮精油乳化物對S. aureus
生菌數（Log CFU/mL）的影響…………………………
100

表十二、不同均質轉速及濃度之文旦皮精油乳化物對E coli生菌數（Log CFU/mL）的影響…………………………………
101
表十三、不同均質轉速的文旦皮精油乳化物抑制S. aureus及 E. coli其生長的最低濃度（MIC, %）………..…………
102
表十四、不同濃度的文旦皮精油乳化物經不同循環次數之微射流處理後對S. aureus生菌數（Log CFU/mL）的影響…….
103
表十五、不同濃度的文旦皮精油乳化物經不同循環次數之微射流處理後對E. coli生菌數（Log CFU/mL）的影響……......
104
表十六、不同濃度之幾丁聚醣對S. aureus及E. coli 生菌數 （Log CFU/mL）的影響……………………………………
105
表十七、不同濃度之文旦皮精油乳化物和幾丁聚醣對S. aureus及E. coli 生菌數（Log CFU/mL）的影響…………………..
106
表十八、於0.4%文旦皮精油乳化物中加入不同濃度之幾丁聚醣對
S. aureus及E. coli生菌數（Log CFU/mL）的影響…............
107
表十九、加入文旦皮精油乳化物、幾丁聚醣及精油乳化物-幾丁聚醣於不同pH值之培養基下對S. aureus抑制率(Inhibitory percentage, %)的影響………………………………………

108
表二十、加入文旦皮精油乳化物、幾丁聚醣及精油乳化物-幾丁聚醣於不同pH值之培養基下對E. colis抑制率(Inhibitory percentage, %)的影響………………………………………

109
表二十一、不同pH值對幾丁聚醣於TSB中界面電位（mV）之影響…………………………………………………………
110

圖目錄

圖一、水蒸餾法萃取之文旦皮精油的GC-MS層析圖譜…………… 111
圖二、文旦皮於30 oC自體酵素反應5天以水蒸餾萃取之精油的GC-MS層析圖譜………………………………………………
112
圖三、文旦皮於30 oC自體酵素反應10天以水蒸餾萃取之精油的GC-MS層析圖譜………………………………………………
113
圖四、文旦皮於30 oC自體酵素反應15天以水蒸餾萃取之精油的GC-MS層析圖譜………………………………………………
114
圖五、文旦皮於30 oC自體酵素反應20天以水蒸餾萃取之精油的GC-MS層析圖譜………………………………………………
115
圖六、文旦皮於30 oC自體酵素反應25天以水蒸餾萃取之精油的GC-MS層析圖譜………………………………………………
116
圖七、蒸氣蒸餾法萃取之文旦皮精油的GC-MS層析圖譜………… 117
圖八、文旦皮於50 oC自體酵素反應2天以蒸氣蒸餾萃取之精油的GC-MS層析圖譜………………………………………………
118
圖九、萃取方法與自體酵素反應之條件對文旦皮精油中主要碳氫萜烯類及含氧萜烯類化合物之轉換率的影響………………..….
119
圖十、萃取方法與自體酵素反應之條件對文旦皮精油萃取率的影響 120
圖十一、文旦皮精油乳化物經不同均質轉速下濃度與殘留菌數之關係……………………………………………………………...
121


圖十二、文旦皮精油乳化物經不同循環次數的微射流後對粒徑響…..……….………………………….…………………….
122
圖十三、幾丁聚醣（DA=54.80%）之改良式高效能液相層析圖…… 123

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