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dc.description.abstract本研究旨在利用超臨界二氧化碳自天然原料中萃取並以管柱純化具有生物活性的物質。實驗將從兩種原料中分成三大部分進行討論。一為植物原料-薑黃,另一為動物原料-甲魚。 第一部分實驗乃利用超臨界二氧化碳在313 K至316 K與24 MPa至26 MPa條件下自新鮮薑黃植物中萃取薑黃精油。精油萃出產率為7 wt%且薑黃酮純度為71 wt%。利用NMR,薄層層析法與液相層析法進行薑黃酮的定性與定量。以低壓正相管柱層析法進行三種薑黃酮的分離純化,可成功地自超臨界二氧化碳薑黃萃出油中分離出86 %純度的ar形式及81 %純度的β+α形式之薑黃酮。萃出之薑黃精油能抑制人類肺癌細胞株的生長與大鼠巨噬細胞株吞噬作用的活性,IC50濃度各為160 μg/mL與4μg/mL。 新鮮薑黃經超臨界二氧化碳脫油後,殘餘之脫油薑黃粉內含10 wt%的薑黃素與其他具活化乙醇去氫酶(ADH)成分。利用超音波乙醇溶液在313 K下萃取脫油薑黃粉240 min,可以回收89 %的薑黃素與得到53 wt%純度的薑黃素。實驗接著將脫油薑黃粉之萃出物處理在經培養之大鼠肝細胞上並觀察細胞釋放ADH的活性。實驗結果指出,利用新鮮薑黃粉為原料與利用超臨界二氧化碳脫油薑黃粉為原料進行萃取後所獲得之兩種萃出物分別能提升16 %與35 %的ADH活性。藉由生化活性的評估,大鼠肝細胞內ADH的活性將歸因於萃出物中薑黃素的含量。 實驗最後,則利用高壓二氧化碳以底向流方式在328 K與55 bar條件下進行甲魚油囊中甲魚油的萃取與回收。回收之甲魚油酯經乙酯化後再經由對流式超臨界二氧化碳在353 K與80 bar下蒸餾油酯中之不飽和脂肪酸成分並於塔底獲得81 wt % C20-24酯肪酸乙酯。濃縮結果將利用Riccati方程式分析萃取槽內脂肪酸組成成分變化情形。濃縮後的甲魚脂肪酸乙酯能有效地促進巨噬細胞大量釋放過氧化氫酶,過氧化氫酶活性可提升至110 mole/min/mL。結果指出,魚油在生物體內的抗氧化能力可經由超臨界二氧化碳濃縮程序而被提升。zh_TW
dc.description.abstractThis study investigated the extraction of bioactive compounds from nature products by using supercritical carbon dioxide (SC-CO2). Experiments were performed for two materials, one is Curcuma longa L. (turmeric) and the other is Pelodiscus sinensis (soft-shelled turtle fish, SST). 7 wt% of turmeric oil yield containing 71 wt% purity of turmerones was obtained from fresh turmeric by using SC-CO2 extraction at 314 K and 25 MPa within 2.5 hr. Three major turmerones were purified from the SC-CO2 extractive turmeric oil by chromatographing in a normal phase silica gel 60 column. 86 wt% purity of ar-turmerone and 81 wt% purity of α+β-turmerone have been obtained. In vitro, this SC-CO2 extractive turmeric oil inhibited the growth of lung cancer cell (A549), showing IC50 of 160 μg/mL, and 50 % of phogocytosis activity in rat macrophage (Raw 264.7) was also inhibited by 4μg/mL of this extracted oil. Following SC-CO2 deoiled process of turmeric material, the residue of SC-CO2 extracted turmeric contains 10 wt% of curcumins and other active compounds of activating alcohol dehydrogenase (ADH). These bioavailable compounds were obtained from this SC-CO2 extracted turmeric by using an ethanol solution ultrasonicated at 313 K for 240 min. 89 % of curcumins was successfully recovered and 53 wt% purity of curcumins was obtained. The ADH activity in rat hepatocytes treated with these extracts of deoiled turmerics has been assayed in vitro. Our experimental results indicated that the extracts of fresh turmeric and SC-CO2 deoiled turmeric increased the ADH enhancement factor by 16 % and 35 %, respectively. This bioavailability investigation clearly evidenced that the enhancing ADH activity in rat hepatocytes was mainly attributed to the content of curcummins in the extract. Finally, this work studied the recovery of omega-3 fatty acids from SST oil bags. 53 wt% crude oil yield was obtained by using pressurized carbon dioxide with top-down fluid flow at 55 bar and 328 K. 81 wt% of C20-24 fatty acid was then enriched using a counter-current SC-CO2 extractive distillation from an esterified oil mixture at 353 K and 250 bar. The column-height versus concentration of C20-24 was examined using the Riccati equation. This refined oil promoted the catalase release of rat macrophage, showing 110 mole/min/mL of catalase activity. The results indicated that the anti-oxidant activity of SST oil was enhanced after SC-CO2 concentration process.en_US
dc.description.tableofcontents摘要 II Abstract IV 目錄 VI 第一章 緒論 1 1. 1. 研究動機 1 1. 1. 1. 薑黃 1 1. 1. 2. 甲魚 2 1. 2. 研究目的與規劃 3 1. 2. 1. 超臨界二氧化碳萃取與純化薑黃精油中之薑黃酮 3 1. 2. 2. 超音波萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 4 1. 2. 3. 超臨界二氧化碳蒸餾乙酯化甲魚油之不飽和脂肪酸 4 第二章 文獻回顧 6 2. 1. 薑黃簡介 6 2. 2. 超臨界二氧化碳萃取薑黃精油的發展 8 2. 3. 薑黃萃出物對乙醇代謝的作用 10 2. 4. 甲魚簡介 12 2. 5. 超臨界流體萃取液態油脂的發展 16 第三章 超臨界二氧化碳萃取與管柱層析薑黃精油之薑黃酮 20 3. 1. 實驗材料與設備 20 3. 1. 1. 新鮮薑黃原料 20 3. 1. 2. 藥品與試劑 20 3. 1. 3. 設備與儀器 24 3. 2. 實驗方法與步驟 29 3. 2. 1. 薑黃精油之萃取程序 29 3. 2. 2. 正相管柱層析三種薑黃酮程序 30 3. 2. 3. 薑黃酮之HPLC定性定量分析 31 3. 2. 4. 水蒸氣蒸餾與超臨界二氧化碳萃取薑黃酮油毒殺人類肺癌細胞株與抑制大鼠巨噬細胞株生化試驗 32 3. 3. 結果與討論 34 3. 3. 1. 三種薑黃酮化學結構分析 34 3. 3. 2. 超臨界二氧化碳萃取薑黃酮油程序 36 3. 3. 3. 實驗設計法最適化超臨界二氧化碳萃取薑黃酮油程序 37 3. 3. 4. 薑黃酮油毒殺人類肺癌細胞株(A549)體外試驗 38 3. 3. 5. 薑黃酮油抑制大鼠巨噬細胞株(RAW 264.7)吞噬作用試驗 39 第四章 超音波溶劑萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 40 4. 1. 實驗材料與設備 40 4. 1. 1. 脫油薑黃原料 40 4. 1. 2. 藥品與試劑 40 4. 1. 3. 設備與儀器 43 4. 2. 實驗方法與步驟 43 4. 2. 1. 薑黃內乙醇代謝成分的萃取方法 44 4. 2. 2. 新鮮薑黃粉與脫油薑黃粉內薑黃素與薑黃酮之HPLC分析 45 4. 2. 3. 新鮮薑黃與脫油薑黃萃出物中總醣含量分析 46 4. 2. 4. 薑黃萃出物對大鼠肝細胞內ADH活性測試 47 4. 3. 結果與討論 50 4. 3. 1. 新鮮薑黃粉內乙醇代謝成分的萃取 51 4. 3. 2. 索式溶劑萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 53 4. 3. 3. 攪拌溶劑萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 53 4. 3. 4. 超音波溶劑萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 55 4. 3. 5. 新鮮薑黃與脫油薑黃萃出物對大鼠肝細內ADH活性影響 56 4. 3. 6. 實驗設計法最適化超音波乙醇萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 60 4. 3. 7. 實驗設計法最適化超音波乙醇水萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 61 4. 3. 8. 薑黃萃出物與市售商品對大鼠肝細胞ADH活性的比較 62 第五章 超臨界二氧化碳萃取甲魚油與蒸餾乙酯化甲魚油中不飽和脂肪酸 64 5. 1. 實驗材料與設備 64 5. 1. 1. 甲魚原料 64 5. 1. 2. 藥品與試劑 64 5. 1. 3. 設備與儀器 67 5. 2. 實驗方法與步驟 68 5. 2. 1. 高壓二氧化碳甲魚油之甲酯化反應 68 5. 2. 2. 高壓二氧化碳甲魚油之乙酯化反應 69 5. 2. 3. 甲魚油脂肪酸組成成分分析 69 5. 2. 4. 乙酯化甲魚油對巨噬細胞內過氧化氫酶(Catalase)活性之測定 70 5. 3. 結果與討論 72 5. 3. 1. 底向流高壓二氧化碳萃取甲魚油 72 5. 3. 2. 對流式超臨界二氧化碳蒸餾乙酯化甲魚油之不飽和脂肪酸 74 5. 3. 3. 超臨界二氧化碳萃取蒸餾管內脂肪酸乙酯組成濃度分佈 79 5. 3. 4. 超臨界二氧化碳魚油乙酯物對巨噬細胞中過氧化氫酶活性的影響 83 第六章 結論 85 6. 1. 超臨界二氧化碳萃取與管柱層析薑黃精油之薑黃酮 85 6. 2. 超音波溶劑萃取超臨界二氧化碳脫油薑黃粉之乙醇代謝成分 85 6. 3. 超臨界二氧化碳萃取甲魚油與蒸餾乙酯化甲魚油中不飽和脂肪酸 87 參考文獻 89 表目錄 表3-1 新鮮薑黃粉內薑黃精油與薑黃酮之萃取實驗結果 97 表3-2 兩變數RSM實驗設計超臨界二氧化碳萃取薑黃酮油 98 表4-1 自新鮮薑黃粉萃取乙醇代謝活性成分實驗數據 99 表4-2 索式溶劑萃取超臨界二氧化碳脫油薑黃粉內乙醇代謝活性成分實驗數據 100 表4-3 攪拌溶劑與液液萃取超臨界二氧化碳脫油薑黃粉內乙醇代謝活性成分實驗數據 101 表4-4 313 K超音波溶劑萃取超臨界二氧化碳脫油薑黃粉內乙醇代謝活性成分實驗數據 102 表4-5 313 K超音波乙醇萃取超臨界二氧化碳脫油薑黃粉內乙醇代謝活性成分實驗數據 103 表4-6 313 K超音波乙醇萃取新鮮薑黃粉內乙醇代謝活性成分實驗數據 104 表4-7 超音波乙醇萃取超臨界二氧化碳脫油薑黃粉內乙醇代謝活性成分實驗設計 105 表4-8 超音波乙醇水溶液萃取超臨界二氧化碳脫油薑黃粉內乙醇代謝活性成分實驗設計 106 表 5-1 高壓二氧化碳萃取甲魚油酯之實驗數據 107 表 5-2 超臨界二氧化碳對流萃取蒸餾甲魚油之實驗數據 108 表 5-3 RICCATI方程式模擬之相關系數 109 表 5-4 超臨界二氧化碳蒸餾實驗數據與文獻數據比較 110 表 5-5 超臨界二氧化碳乙酯油濃縮物對RAW 264.7內CATALASE酵素釋放的影響 111 圖目錄 圖2-1 三種薑黃素的化學結構式 112 圖2-2 三種薑黃酮之化學結構式 113 圖3-1 水蒸氣蒸餾萃取薑黃精油流程簡圖 114 圖3-2 超臨界二氧化碳萃取薑黃精油流程簡圖 115 圖3-3 正相管柱層析分離三種薑黃酮 116 圖3-4 薑黃樣品的HPLC圖譜 117 圖3-5 86 % AR-TURMERONE EI-MS圖譜 118 圖3-6 超臨界二氧化碳與水蒸氣蒸餾萃取薑黃精油的比較 119 圖3-7 流速對超臨界二氧化碳萃取薑黃精油與薑黃酮的影響 120 圖 3-8 RSM實驗設計溫度與壓力對萃取薑黃精油產率,三種薑黃酮與三種薑黃素純度的影響 121 圖3-9 水蒸氣薑黃精油對A549人類肺癌細胞之存活率關係 122 圖3-10 SC-CO2薑黃精油對A549人類肺癌細胞之存活率關係 123 圖3-11 SC-CO2薑黃精油對大鼠巨噬細胞株 (RAW 264.7) 之存活率與吞噬比值 124 圖4-1 索式溶劑萃取裝置圖 125 圖4-2 各種薑黃萃出物的HPLC圖譜 126 圖4-3 薑黃萃出物對等數大鼠肝細胞細胞增生率與ADH活性的影響 127 圖4-4 各種溶劑萃取新鮮與脫油薑黃粉內乙醇代謝活性成分流程圖 128 圖4-5 標準品對大鼠肝細胞內ADH活性的影響 129 圖4-6 新鮮薑黃萃出物對大鼠肝細胞內ADH活性的影響 130 圖4-7 脫油薑黃粉之索式萃出物對大鼠肝細胞內ADH活性的影響 131 圖4-8 脫油薑黃粉末之超音波萃出物對大鼠肝細胞內ADH活性的影響 132 圖4-9 新鮮薑黃與脫油薑黃之超音波乙醇萃出物對大鼠肝細胞內ADH活性的影響 133 圖4-10 超臨界二氧化碳脫油薑黃粉之攪拌溶劑與液液萃取萃出物對大鼠肝細胞內ADH活性的影響 134 圖4-11 RSM實驗設計超音波乙醇萃取超臨界二氧化碳脫油薑黃粉 135 圖4-12 RSM實驗設計超音波乙醇水萃取超臨界二氧化碳脫油薑黃粉 136 圖4-13 本研究薑黃萃出物與市售產品中薑黃素與薑黃酮含量的比較 137 圖4-14 本研究40 PPM薑黃萃出物與市售產品提升ADH活性的比較 138 圖5-1 高壓二氧化碳萃取甲魚油乙酯物流程簡圖 139 圖5-2 對流式超臨界二氧化碳蒸餾乙酯化甲魚油裝置圖 140 圖5-3 對流式超臨界二氧化碳蒸餾乙酯化甲魚油流程簡圖 141 圖5-4 對流式超臨界二氧化碳蒸餾乙酯化甲魚油操作條件簡圖 142 圖5-5 超臨界二氧化碳蒸餾乙酯化甲魚油蒸餾管充填結構 143 圖5-6 二氧化碳壓力對甲魚油脂肪酸組成成分的影響 144 圖5-7 超臨界二氧化碳萃取蒸餾塔頂 (A) 與塔底 (B) 脂肪酸組成濃度分布 145 圖5-8 實驗設計最適化塔底C20-24脂肪酸組成濃度的影響 146 圖5-9 RICCATI方程式計算超臨界二氧化碳蒸餾管內C20-24脂肪酸組成濃度分布 147 圖5-10 超臨界二氧化碳蒸餾管內塔頂與塔底脂肪酸組成成分GC圖譜 148 附表與附圖 附表3-1 超臨界二氧化碳萃取薑黃酮油產率之變方分析 150 附表3-2 超臨界二氧化碳萃取三種薑黃酮之變方分析 151 附表3-3 超臨界二氧化碳萃取三種薑黃酮純度之變方分析 152 附表4-1 超音波乙醇萃取超臨界二氧化碳脫油薑黃粉末薑黃素萃取效率之變方分析 153 附表4-2 超音波乙醇萃取超臨界二氧化碳脫油薑黃粉末薑黃素純度之變方分析 154 附表4-3 超音波乙醇萃取超臨界二氧化碳脫油薑黃粉萃出物對大鼠肝細胞內ADH活性之變方分析 155 附表4-4 超音波乙醇水萃取超臨界二氧化碳脫油薑黃粉末薑黃素萃取效率之變方分析 156 附表4-5 超音波乙醇水萃取超臨界二氧化碳脫油薑黃粉末薑黃素純度之變方分析 157 附表4-6 超音波乙醇水萃取超臨界二氧化碳脫油薑黃粉萃出物對大鼠肝細胞內ADH活性之變方分析 158 附表5-1 超臨界二氧化碳萃取蒸餾塔底C20-24脂肪酸濃度之變方分 159 附圖 2-1 薑黃素抑制癌細胞生長之相關文獻 160 附圖 3-1 三種薑黃酮標準品 (AR-TURMERONE AND Α+Β-TURMERONE) 檢量線 161 附圖 3-2 薄層層析法 ( TLC AT 254 NM)分離純化三種薑黃酮 162 附圖 3-2 薄層層析法 ( TLC AT 254 NM)分離純化三種薑黃酮 (續) 163 附圖 3-3 86% AR-TURMERONE 之1H-NMR圖譜 164 附圖 3-4 86% AR-TURMERONE 之13C-NMR圖譜 165 附圖 3-5 81% Α+Β-TURMERONE之1H-NMR圖譜 166 附圖 3-6 81% Α+Β-TURMERONE之1H-NMR圖譜 (COSEY) 167 附圖4-1 三種薑黃素 ( CURCUMIN I, II, AND III ) 標準品檢量線 168 附圖5-1 甲魚油酯之十二種單元脂肪酸化學結構式 169 附圖5-1 甲魚油酯之十二種單元脂肪酸化學結構式 (續) 170 附圖5-2 十二種脂肪酸甲酯標準品檢量線 171zh_TW
dc.subjectSupercritical fluiden_US
dc.subjectalcohol dehydrogenase (ADH)en_US
dc.subjectsoft shelled turtle fishen_US
dc.subjectfatty aciden_US
dc.titleSeparation of bioactive compounds from Curcuma longa L. and Pelodiscus sinensis by using supercritical carbon dioxideen_US
dc.typeThesis and Dissertationzh_TW
item.openairetypeThesis and Dissertation-
item.fulltextno fulltext-
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