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輔仁大學
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營養科學系
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研
究 高彩華
生
(中)
研
究 Tsai-Hua Kao
生
(英)
論
文
由豆渣製備異黃酮素粉末及其生理活性之研究
名
稱
(中)
論
文 A Study on Processing and Physiological Activity of Isoflavone Powder from
名
Soybean Cake
稱
(英)
其
他
題
名
指
導
陳炳輝
教
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(中)
指
導
Bing-Huei Chen
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(英)
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01
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位
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別
博士
畢
業
學
年
度
95
出
版
年
語
文
別
中文
關
鍵
字
豆渣 異黃酮素 製備型管柱層析 抗氧化 抗發炎
(中)
關
鍵 soybean cake isoflavone preparative column chromatography antioxidant activity
字 antiinflammatory activity
(英)
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??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??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
摘 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
要
萄糖基異黃酮素。以 Yamazen Hi-FlashTM 矽膠管柱層析，動相為正己烷(中)
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?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 IL1?、IL-6、一氧化氮及 PGE2 等發炎媒介物生成。
摘
要
Isoflavones, an important class of flavonoids, are mainly present in soybean.
Soybean has been shown to contain twelve isoflavones in four different chemical
(英) 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 waterethanol 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.
論
文
目
次
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
參
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