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研究生:高彩華
研究生(外文):Tsai-Hua Kao
論文名稱:由豆渣製備異黃酮素粉末及其生理活性之研究
論文名稱(外文):A Study on Processing and Physiological Activity of Isoflavone Powder from Soybean Cake
指導教授:陳炳輝陳炳輝引用關係
指導教授(外文):Bing-Huei Chen
學位類別:博士
校院名稱:輔仁大學
系所名稱:食品營養學研究所博士班
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:2007
畢業學年度:95
語文別:中文
論文頁數:318
中文關鍵詞:豆渣異黃酮素製備型管柱層析抗氧化抗發炎
外文關鍵詞:soybean cakeisoflavonepreparative column chromatographyantioxidant activityantiinflammatory activity
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異黃酮素是黃豆中主要的類黃酮素,共有十二種衍生物,又可分為四群,包括丙二醯葡萄糖基異黃酮素、葡萄糖基異黃酮素、乙醯葡萄糖基異黃酮素及不含糖基異黃酮素。豆渣為油脂加工的廢棄物,許多研究顯示,去脂黃豆粉中仍含有高量的異黃酮素,本研究目的即是萃取純化豆渣中的異黃酮素,製備成粉末,進一步探討粉末之生理功能。
本研究共分為五個實驗,實驗一比較溶劑及超臨界二氧化碳萃取豆渣之效果,並探討以-葡萄糖苷酶作用含糖基異黃酮素以提高不含糖基異黃酮素產量之方法,此外,亦評估擔體種類、擔體使用量和乾燥條件對製備異黃酮素粉末的影響。結果顯示,溶劑對於丙二醯葡萄糖基、葡萄糖基異黃酮素和異黃酮素總量的萃取效果較超臨界二氧化碳佳,但乙醯葡萄糖基和不含糖基異黃酮素則是以超臨界二氧化碳萃取效果較好。利用-葡萄糖苷酶50 U/mL作用2小時,即可生成高量不含糖基異黃酮素。以冷凍乾燥製備粉末,褐藻酸鈉的最適含量為1 %,而γ-聚麩胺酸鈉則為0.003 %,粉末中分別含4.3 %及4.8 %異黃酮素;以真空乾燥製備粉末,褐藻酸鈉的最適含量為0.04 %,而γ-聚麩胺酸鈉則為0.01 %,粉末中分別含5.4 %及5.7 %異黃酮素。
實驗二探討管柱層析配合不同吸附劑或膠體對於分離異黃酮素之效果,並評估大量製備四群異黃酮素之方法,結果顯示,豆渣萃取液以Diaion HP-20為靜相,經15 %及27 %的乙醇水溶液沖提,可分別得到丙二醯葡萄糖基異黃酮素及葡萄糖基異黃酮素。以Yamazen Hi-FlashTM矽膠管柱層析,動相為正己烷-異丙醇-乙醇(8:9:1, v/v/v),則可分離出不含糖基異黃酮素和乙醯葡萄糖基異黃酮素,四群異黃酮素之含量分別為丙二醯葡萄糖基異黃酮素244.26 μg/mg、葡萄糖基異黃酮素179.04 μg/mg、乙醯葡萄糖基異黃酮素21.25 μg/mg及不含糖基異黃酮素11.88 μg/mg。
實驗三探討由管柱層析製備四群豆渣之異黃酮素萃取液之抗氧化活性,並測定其他抗氧化活性成分。結果顯示,異黃酮素萃取液具有清除DPPH及ABTS․+自由基、螯合亞鐵離子、抑制共軛雙烯生成及降低TBARS之效果,但異黃酮素萃取液之還原能力較差。萃取液中以乙烯葡萄糖基和不含糖基效果最佳,且萃取液之抗氧化活性較單一標準品高。萃取液中的其他抗氧化活性成分包括皂苷和酚類化合物等。
實驗四探討由管柱層析製備四群豆渣之異黃酮素萃取液之抑制肝癌細胞HepG2生長之效果。結果顯示,異黃酮素可抑制肝癌細胞HepG2之生長,並使細胞週期停滯於G2/M期。無論是標準品或是萃取液,不含糖基及含乙醯葡萄糖基異黃酮素之效果皆優於葡萄糖基及丙二醯葡萄糖基衍生物。
實驗五探討不同異黃酮素粉末之抗發炎效果,結果發現,由豆渣製備的異黃酮素粉末及genistein皆可有效抑制發炎,降低發炎小鼠血液中白血球含量、減少小鼠腹腔細胞培養上清液及腹腔抽出液IL-1、IL-6、一氧化氮及PGE2等發炎媒介物生成。
Isoflavones, an important class of flavonoids, are mainly present in soybean. Soybean has been shown to contain twelve isoflavones in four different chemical forms: malonylglucoside, glucoside, acetylglucoside and aglycone. Soybean cake, a by-product obtained during processing of soybean oil, was reported to be a rich source of functional components such as isoflavones. The objectives of this study were to isolate four different isoflavone fractions from soybean cake by preparative column chromatography and process into powder, and determine their physiological activity.
This study are divided into five different experimental studies. The first part compared the effect of organic solvent and supercritical CO2 on extraction efficiency of isoflavone, and studied the conversion of isoflavone glucosides to its corresponding aglycones as affected by -glucosidase. In addition, the effects of different carriers and drying methods on the quality of isoflavone powder was evaluated. Results showed solvent extraction could result in a high yield of malonylglucoside and glucoside isoflavones, while a greater efficiency was found for acetylglucoside and aglycone isoflavones by supercritical CO2. After incubation with 50 U/mL -glucosidase for 2 h, most isoflavone glucosides were converted into aglycones. With the optimum concentrations of sodium alginate (1%) and -PGA (0.003%) during freeze drying, the isoflavone contents in the powder were 4.3 and 4.8 %, respectively. But, with sodium alginate and -PGA at a level of 0.04 and 0.01 respectively, a vacuum-dried powder product containing 5.4 and 5.7 % isoflavone was produced.
In the second experiment, various adsorbents and solvent systems were compared with respect to the separation efficiency of four groups of isoflavones in soybean cake by preparative column chromatography. Results revealed Diaion HP-20 to be the most appropriate adsorbent to separate malonylglucosides and glucosides by using a solvent system of deionized water-ethanol in a ratio of 85:15 (v/v) and 73:27 (v/v), respectively. Both acetylglucosides and aglycones were separated with a silica gel adsorbent by employing a solvent system of n-hexane-isopropanol-ethanol (8:9:1, v/v/v). A total amount of 244.26, 179.04, 21.25 and 11.88μg/mg based on dry weight were obtained for malonylglucosides, glucosides, acetylglucosides and aglycones, respectively.
Third, the antioxidant activity of four fractions of isoflavones from soybean cake by different assays was examined. All the four isoflavone fractions exhibited a high efficiency in scavenging DPPH and ABTS․+ free radicals, chelating metal ions and inhibiting both conjugated diene and TBARS formation. However, a low reducing power was observed for all the isoflavone fractions. Overall, both the acetylglucoside and aglycone fractions showed a high antioxidant activity, with a mixture of isoflavone standards showing a better antioxidant activity than single isoflavone standard.
The fourth part of this study includes the evaluation of antiproliferation effect in HepG2 cells by isoflavone fractions from soybean cake. Isoflavone fractions from soybean cake were efficient in inhibiting HepG2 cell growth and arresting cell-cycle in G2/M phase. Both the acetylglucoside and aglycone fraction were more effective in antiproliferation effect than the other fractions.
Finally, the antiinflammatory effect of isoflavone powder was investigated. Both isoflavone powder and genistein standard showed a high efficiency in decreasing leukocyte number in mice blood and lowering the secretions of IL-1、IL-6、nitric oxide and PGE2 in peritoneal exudated cell supernatant and peritoneal exudated fluid.
第一章 文獻回顧………………………………………………………. 1
一、異黃酮素之化學結構……………………..…………………. 1
二、異黃酮素之物化性質……………….…………..…………… 1
三、異黃酮素之萃取………………………………………..….… 6
(一)溶劑萃取…………………………………………………… 6
(二)超臨界流體萃取……………………………………………. 10
1. 超臨界流體萃取之原理及特性………………………….. 11
2. 超臨界二氧化碳對於異黃酮素之萃取………………….. 20
四、異黃酮素之製備……………………………………………… 21
五、異黃酮素之分離……………………………………………… 22
六、異黃酮素之安定性…………………………………………… 24
七、異黃酮素之吸收……………………………………………… 29
八、異黃酮素之代謝……………………………………………… 33
九、異黃酮素之生理活性…………………………………………. 38
(一)預防心血管疾病發生……………………………………… 38
(二)抗氧化性…………………………………………………… 39
(三)預防癌症發生………………………………………………. 40
(四)減緩更年期徵候……………………………………………. 42
(五)預防骨質疏鬆………………………………………………. 43
(六)調節免疫功能………………………………………………. 44
第二章、豆渣異黃酮素萃取及粉末製備之研究……………………… 47
一、前言…………………………………………………………… 47
二、材料與方法…………………………………………………… 49
(一)材料與儀器………………………………………………… 49
(二)實驗方法…………………………………………………… 50
1. 豆渣異黃酮素之萃取…………………………………….. 50
目 錄
(1)溶劑萃取……………………………………………….. 50
(2)超臨界二氧化碳萃取…………………………………. 51
2. 酵素轉換之評估…………………………………………….. 51
3. 粉末製備之評估…………………………………………….. 54
4. 異黃酮素之定性…………………………………………….. 57
5. 異黃酮素之定量…………………………………………….. 58
6. HPLC分析條件……………………………………………… 59
7. 粉末水分含量測定………………………………………….. 60
8. 統計分析…………………………………………………….. 60
三、結果與討論………………………………………………………… 61
(一)豆渣異黃酮素之萃取…………………………………………… 61
1. 溶劑萃取…………………………………………………….. 61
2. 超臨界二氧化碳萃取……………………………………….. 64
(1)壓力之影響………………………………………………. 65
(2)溫度之影響………………………………………………. 71
(3)溶劑與超臨界二氧化碳對萃取豆渣異黃酮素效果之比較………………………………………………………….
80
3. 酵素轉換之評估…………………………………………….. 86
4. 粉末製備之評估…………………………………………….. 100
四、結論………………………………………………………………… 131
第三章、以管柱層析法製備四群異黃酮素之研究………………………… 133
一、前言………………………………………………………………… 133
二、材料與方法………………………………………………………… 135
(一)材料與儀器……………………………………………………… 135
(二)實驗方法………………………………………………………… 137
1. 豆渣異黃酮素之萃取………………………………………….. 137
2. 吸附劑及膠體之評估………………………………………….. 137
3. 大量製備異黃酮素之評估…………………………………….. 138

4. 異黃酮素之定性……………………………………………….. 139
5. 異黃酮素之定量……………………………………………….. 139
6. HPLC分析條件………………………………………………… 140
7. 統計分析……………………………………………………….. 140
三、結果與討論………………………………………………………… 142
(一)豆渣異黃酮素之含量…………………………………………… 142
(二)吸附劑評估……………………………………………………… 142
(三)大量製備之評估………………………………………………… 146
四、結論………………………………………………………………… 151
第四章、四群異黃酮素萃出液之抗氧化活性……………………………… 152
一、前言………………………………………………………………… 152
二、材料與方法………………………………………………………… 154
(一)材料與儀器……………………………………………………… 154
(二)實驗方法………………………………………………………… 159
1萃取液中其他抗氧化成分之測定.…………………………….. 159
2.抗氧化活性測試………………………………………………… 164
(1)清除DPPH自由基能力之評估…………………………….…. 164
(2)TEAC(Trolox Equivalent Antioxidant Capacity)…………… 165
(3)螯合亞鐵離子能力之評估…………………………………….. 168
(4)還原能力之評估……………………………………………….. 168
(5)抑制共軛雙烯生成之評估…………………………………….. 169
(6)抑制微脂粒(liposome)氧化之評估(TBARS法)……….. 170
3. 統計分析……………………………………………………….. 171
三、結果與討論………………………………………………………… 172
1萃取液中其他抗氧化成分之測定.…………………………….. 175
2.抗氧化活性測試………………………………………………… 184
(1)清除DPPH自由基能力之評估…………………………….…. 184
(2)TEAC(Trolox Equivalent Antioxidant Capacity)…………… 187


(3)螯合亞鐵離子能力之評估…………………………………….. 192
(4)還原能力之評估……………………………………………….. 195
(5)抑制共軛雙烯生成之評估…………………………………….. 199
(6)抑制微脂粒(liposome)氧化之評估(TBARS法)……….. 201
四、結論………………………………………………………………… 205
第五章、四群異黃酮素萃出液抑制肝癌細胞生長之影響…………………. 206
一、前言………………………………………………………………… 206
二、材料與方法………………………………………………………… 208
(一)材料與儀器……………………………………………………… 208
(二)實驗方法………………………………………………………… 209
1. 由豆渣中製備異黃酮素萃取液……………………………….. 209
2. 各處理組濃度配製…………………………………………….. 210
3. 細胞培養液配製……….……………………...……………….. 212
4. MTT溶液配製……….……………………...………………….. 212
5. 細胞培養……………………………………………………….. 212
6. 細胞繼代……………………………………………………….. 213
7. 細胞保存……………………………………………………….. 213
8. 人類肝癌細胞HepG2對異黃酮素萃取溶劑之耐受性測試… 214
9. 細胞活性測試………………………………………………….. 216
10. 異黃酮素萃出液抑制人類肝癌細胞HepG2生長之評估…... 216
11. 細胞週期分析…………………….…………………………... 217
12. 統計分析……………………………………………………… 217
三、結果與討論……………………………………………………….. 218
(一)人類肝癌細胞HepG2對異黃酮素萃取溶劑之耐受性………. 218
(二)細胞活性測試...………………………………………………… 218
(三)異黃酮素萃取液及標準品抑制HepG2細胞株增生之效果(MTT test)………………………………………………………
218
(四)細胞週期分析…………………………………………………… 229

四、結論………………………………………………………………… 239
第六章、異黃酮素粉末抑制小鼠發炎反應之評估………………………… 240
一、前言………………………………………………………………… 240
二、材料與方法………………………………………………………… 243
(一)試藥與材料……………………………………………………… 243
(二)實驗方法………………………………………………………… 249
1. 粉末其他機能性成分測定…………………………………….. 249
2. 實驗動物之飼養……………………………………………….. 249
3. 實驗動物分組………………………………………………….. 250
4. 誘導發炎……………………………………………………….. 251
5. 動物犧牲及樣品取得………………………………………….. 251
6. 發炎相關指標測試…………………………………………….. 253
7. 統計分析……………………………………………………….. 259
三、結果與討論………………………………………………………... 260
(一)粉末其他機能性成分測定……………………………………. 260
(二)異黃酮素粉末對小鼠體重之影響……………………………. 260
(三)異黃酮素粉末對發炎模式小鼠白血球含量之影響…………. 260
(四)異黃酮素粉末對發炎模式小鼠促發炎相關物質生成之影響 265
四、討論………………………………………………………............... 289
五、結論………………………………………………………............... 294
參考文獻………………………………………………..……………………. 295
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