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研究生:張志偉
研究生(外文):Chih-Wei Chang
論文名稱:以管柱層析法自米糠中製備生產米糠醇以及植物固醇
論文名稱(外文):Preparative Production of γ-Oryzanol and Phytosterols from Rice Bran by Column Chromatography
指導教授:賴世明賴世明引用關係
指導教授(外文):Shih-Ming Lai
學位類別:碩士
校院名稱:國立雲林科技大學
系所名稱:工業化學與災害防治研究所
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2004
畢業學年度:92
語文別:中文
論文頁數:259
中文關鍵詞:米糠米糠醇植物固醇管柱層析製備生產分離純化
外文關鍵詞:Phytosterolsr-OryzanolRice branPreparative scaleIsolationPurification
相關次數:
  • 被引用被引用:6
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米糠醇以及植物固醇均為米糠中的重要成份,具有防止老化降低血膽固醇含量等功效,且有抗氧化功能可治療心血管病變,因此可作為醫療藥品及健康食品。由於米糠醇以及植物固醇在米糠油中所佔含量甚低(分別為2-3%與1-2%),因此必須加以分離與純化,以達實用之途。目前文獻上常見純化與分離米糠醇以及植物固醇之方法包括一些吸附或液相萃取純化法,其步驟相當煩瑣、費時,且通常只有分析的用途。本研究之目的即在於發展一效率佳且適合大規模化之技術來產製純度達80%以上以及回收率達70%以上的米糠醇以及植物固醇。
研究結果顯示,首先以每批200 g的新鮮米糠,並經700 ml的正己烷溶劑以電熱板加熱-迴流萃取法萃取1小時為最佳萃取條件,其粗米油的萃取率約為11~12%,且其中含米糠醇與植物固醇的純度分別約為2.0~2.5%與0.5~1.0%。接著,採兩種路徑來分離純化米糠醇以及植物固醇。第一路徑直接由粗米油分離純化有效成份時,以製備級矽膠不鏽鋼管柱採正己烷/異丙醇(1%醋酸)=99/1與正己烷/乙酸乙酯=90/10進行沖提層析為較佳的條件,在純度方面,可達到大於80%以上的米糠醇與大於60%以上的植物固醇;在回收率方面,米糠醇回收率可達到90%以上,植物固醇回收率約30~70%;在產率方面,經過多次注入粗米油(約250 mg),僅可得到米糠醇約5 mg與植物固醇約1 mg。第二路徑採初步濃縮與進一步分離純化兩階段,第一階段初步濃縮方面,以製備級矽膠玻璃管柱採用吸附與脫附之階梯層析方式操作,其所收集米糠醇純度可達到17~20%,植物固醇純度約為6%;在產率方面,一次放大的管柱操作可得約6 g初步濃縮液。第二階段進一步分離純化有效成份時,以採用製備級矽膠不鏽鋼管柱的正己烷/乙酸乙酯=90/10進行沖提層析為較佳的條件,在純度方面,可達到約30%的米糠醇與20%的植物固醇;在回收率方面,米糠醇回收率可達到90%以上,植物固醇回收率約60%;在產率方面,經過兩次注入初步濃縮液(約1003 mg),可得到米糠醇約150 mg與植物固醇約40 mg。兩路徑的比較如下:第一路徑可得到較高純度的米糠醇與植物固醇(分別為>80%與>60%),但所得產率相當低(多次注入分別只收集約為5 mg與1 mg);而第二路徑之第二階段所得純度不高(分別約為30%與20%),但可得到高產率的米糠醇與植物固醇(兩次注入分別收集約為150 mg與40 mg)。
��-Oryzanol and phytosterols are considered to be important fractions in rice bran. They possess hypocholesterolemic activity that may help to reduce the cholesterol levels in humans. They also possess antioxidant property that may help to protect against various vascular diseases in biological systems. Due to the low concentration levels of ��-oryzanol (2-3%) and phytosterols (1-2%) in crude rice bran oil (CRBO), isolation, separation and purification would be necessary before a practical usage. Current procedures for the isolation and purification of ��-oryzanol and phytosterols from rice bran oil involve some adsorptive or extractive purification, which are tedious and time-consuming and are only for analytical purpose. To overcome these problems, this study is aimed to develop an efficient and easy-to-scale-up technique for the isolation and purification of ��-oryzanol and phytosterols that contains 80+% purity and 70+% recovery.
The results show that, first, the CRBO was prepared using an extractor with hot-plate heating and solvent refluxing operated under an optimal extraction condition (using 700 ml of hexane for 1 hr per 200 g rice bran). The extraction yield was 11~12% and the purities of ��-oryzanol and phytosterols in the CRBO were 2.0~2.5% and 0.5~1.0%, respectively. Then, ��-oryzanol and phytosterols in the CRBO were separated and purified by two routes. For the first route, ��-oryzanol and phytosterols were separated and purified directly from the CRBO by using elution chromatography with a preparative stainless silica gel column operated under an optimal elution condition (mobile phase compositions of hexane/isopropyl alcohol (1% acetic acid)= 99/1 and hexane/ethyl acetate=90/10). The purities of ��-oryzanol and phytosterols were about 80+% and 60+%, respectively, the recoveries of ��-oryzanol and phytosterols were about 90+% and 30~70%, respectively, and after several times of the above injection (about 250 mg CRBO injected), the yields of ��-oryzanol and phytosterols were about 5 mg and 1 mg, respectively. For the second route, ��-oryzanol and phytosterols were concentrated together by using frontal chromatography with a preparative glass silica gel column in the first stage and then separated and purified by using elution chromatography with a preparative stainless silica gel column in the second stage. In the first stage, the purities of ��-oryzanol and phytosterols were about 17~20% and 6%, respectively, and the yield of the concentrate was about 6 g per column operation. In the second stage, the purities of ��-oryzanol and phytosterols were about 30% and 20%, respectively, the recoveries of ��-oryzanol and phytosterols were about 90+% and about 60%, respectively, and after two times of the above injection (about 1003 mg concentrate injected), the yields of ��-oryzanol and phytosterols were about 150 mg and 40 mg, respectively. The system performances of the two routes were compared as follows: for the active compounds, ��-oryzanol and phytosterols, respectively, higher purities (80+% and 60+%) but lower yields (about 5 mg and 1 mg) were obtained in the first route in contrast to lower purities (30% and 20%) but higher yields (about 150 mg and 40 mg) obtained in the second route.
中文摘要 ------------------------------------------------------------------------ i
英文摘要 ------------------------------------------------------------------------ iii
誌謝 ------------------------------------------------------------------------ v
目次 ------------------------------------------------------------------------ vi
表目次 ------------------------------------------------------------------------ ix
圖目次 ------------------------------------------------------------------------ xi
符號說明 ------------------------------------------------------------------------ xv
一、 緒論------------------------------------------------------------------ 1
1.1 研究動機------------------------------------------------------------ 1
1.2 研究目的及方法--------------------------------------------------- 1
二、 文獻回顧與理論部分--------------------------------------------- 4
2.1 米糠的營養價值--------------------------------------------------- 4
2.2 米糠油--------------------------------------------------------------- 4
2.2.1 米糠油的組成------------------------------------------------------ 4
2.2.2 精煉米糠油的加工程序------------------------------------------ 6
2.3 米糠醇與植物固醇------------------------------------------------ 6
2.3.1 米糠醇與植物固醇的性質及結構------------------------------ 6
2.3.2 米糠醇與植物固醇的機能性與應用--------------------------- 11
2.3.3 製備生產米糠醇與植物固醇之相關研究--------------------- 14
2.3.4 米糠醇與植物固醇之分析方法--------------------------------- 16
2.4 正相/逆相分離機制------------------------------------------------ 16
2.5 製備級液相層析的操作模式------------------------------------ 19
2.6 沖提層析法量測分離解析度------------------------------------ 24
2.7 濃縮純化性能------------------------------------------------------ 27
三、 實驗部分------------------------------------------------------------ 28
3.1 實驗材料與儀器--------------------------------------------------- 28
3.1.1 實驗材料------------------------------------------------------------ 28
3.1.2 實驗儀器------------------------------------------------------------ 30
3.2 有效成份之HPLC定性與定量分析--------------------------- 35
3.3 粗米油的提取------------------------------------------------------ 37
3.3.1 提取方法與步驟--------------------------------------------------- 37
3.3.2 粗米油不經去膠去臘與經去膠去臘的比較------------------ 40
3.4 直接由粗米油分離純化米糠醇與植物固醇的製備級液相層析術---------------------------------------------------------------
40
3.4.1 正相系統的沖提層析--------------------------------------------- 40
3.4.2 正相系統的階梯層析--------------------------------------------- 43
3.5 粗米油中米糠醇與植物固醇的進一步提取濃縮(製備初步濃縮液)-----------------------------------------------------------
47
3.5.1 矽膠玻璃管柱之處理--------------------------------------------- 47
3.5.2 提取濃縮操作流程------------------------------------------------ 47
3.5.2.1 半製備級矽膠玻璃管柱------------------------------------------ 48
3.5.2.2 製備級矽膠玻璃管柱--------------------------------------------- 50
3.6 由初步濃縮液分離純化米糠醇與植物固醇的製備級液相層析術---------------------------------------------------------------
52
3.6.1 逆相系統的沖提層析--------------------------------------------- 52
3.6.2 逆相系統的階梯層析--------------------------------------------- 55
3.6.2.1 C8不鏽鋼管柱 55
3.7 製備純化標準品Campesterol與β-Sitosterol的製備級液相層析術---------------------------------------------------------------
57
四、 結果與討論--------------------------------------------------------- 59
4.1 有效成份之HPLC定性與定量分析--------------------------- 59
4.1.1 米糠提取物--------------------------------------------------------- 59
4.1.1.1 正相HPLC分析--------------------------------------------------- 59
4.1.1.2 逆相HPLC分析--------------------------------------------------- 64
4.1.1.3 正相與逆相HPLC分析比較------------------------------------ 67
4.1.2 粗米油濃縮物------------------------------------------------------ 67
4.1.2.1 正相HPLC分析--------------------------------------------------- 67
4.1.2.2 逆相HPLC分析--------------------------------------------------- 70
4.1.2.3 正相與逆相HPLC分析比較------------------------------------ 74
4.2 粗米油的製備------------------------------------------------------ 74
4.2.1 提取裝置的選擇--------------------------------------------------- 74
4.2.2 電熱板加熱-迴流提取法的最佳化----------------------------- 77
4.2.2.1 米糠量--------------------------------------------------------------- 77
4.2.2.2 提取溶劑用量------------------------------------------------------ 77
4.2.2.3 提取時間------------------------------------------------------------ 82
4.2.2.4 提取溶劑種類------------------------------------------------------ 82
4.2.3 不經去膠去臘與經去膠去臘程序的比較--------------------- 87
4.3 直接由粗米油分離純化米糠醇與植物固醇------------------ 87
4.3.1 最佳層析系統的選取------------------------------------------- 90
4.3.2 製備級分離純化粗米油中的米糠醇與植物固醇------------ 93
4.3.2.1 沖提層析------------------------------------------------------------ 95
4.3.2.2 階梯層析------------------------------------------------------------ 103
4.3.2.2.1 吸附操作:吸附處理量(貫穿曲線)之量測------------------- 106
4.3.2.2.2 脫附操作:階段沖提程式之建立------------------------------ 106
4.3.2.3 各系統性能的比較------------------------------------------------ 114
4.4 初步濃縮液的製備------------------------------------------------ 115
4.4.1 半製備級矽膠玻璃管柱之操作--------------------------------- 116
4.4.1.1 吸附操作:吸附處理量(貫穿曲線)之量測------------------- 116
4.4.1.2 脫附操作:階段沖提程式之建立------------------------------ 118
4.4.2 製備級矽膠玻璃管柱之放大操作------------------------------ 124
4.4.2.1 吸附操作:吸附處理量(貫穿曲線)之量測------------------- 125
4.4.2.2 脫附操作:階段沖提程式之建立------------------------------ 125
4.5 由初步濃縮液分離純化米糠醇與植物固醇------------------ 130
4.5.1 最佳層析系統的選取--------------------------------------------- 130
4.5.2 製備級分離濃縮初步濃縮液中的米糠醇與植物固醇------ 141
4.5.2.1 逆相系統------------------------------------------------------------ 141
4.5.2.1.1 沖提層析------------------------------------------------------------ 143
4.5.2.1.2 階梯層析------------------------------------------------------------ 160
4.5.2.1.3 逆相系統性能的比較--------------------------------------------- 168
4.5.2.2 正相系統------------------------------------------------------------ 168
4.5.2.2.1 沖提層析------------------------------------------------------------ 169
4.5.2.2.2 兩正相系統性能的比較------------------------------------------ 191
4.5.2.3 逆相與正相系統的比較------------------------------------------ 194
4.6 進一步以結晶法純化米糠醇與植物固醇--------------------- 195
五、 結論------------------------------------------------------------------ 196
六、 參考文獻------------------------------------------------------------ 200
附錄A 製備標準品Campesterol與β-Sitosterol----------------------- 206
附錄B 以小量注入於正相不鏽鋼管柱的沖提層析圖譜------------ 227
附錄C 矽膠玻璃管柱的層析圖譜--------------------------------------- 236
附錄D 以小量注入於逆相不鏽鋼管柱的沖提層析圖譜------------ 251
自述 ------------------------------------------------------------------------ 259
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