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研究生:李婕妘
研究生(外文):Jie-Yun Li
論文名稱:大豆與味噌中生物活性指標化合物之化學分析
論文名稱(外文):The chemical analysis of bioactive markers in soybean and miso
指導教授:呂廷璋
口試日期:2017-07-27
學位類別:碩士
校院名稱:國立臺灣大學
系所名稱:食品科技研究所
學門:農業科學學門
學類:食品科學類
論文種類:學術論文
論文出版年:2017
畢業學年度:105
語文別:中文
論文頁數:111
中文關鍵詞:大豆味噌大豆異黃酮大豆皂素植物固醇液相層析串聯質譜儀
外文關鍵詞:soybeanmisoisoflavonessoyasaponinsphytosterolsliquid chromatography–mass spectrometry
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大豆含有許多具生理活性之植化素,其中以大豆異黃酮與大豆皂素為主,亦含有植物固醇與生育醇等脂溶性化合物,同時為良好的蛋白質、脂質等營養素來源。為瞭解台灣產大豆原料與其製成的發酵產品中質化素之含量,本研究欲利用高效液相層析串聯質譜儀搭配光學檢測器,分別建立兩個分析平台進行大豆異黃酮與大豆皂素、植物固醇與生育醇之測定,分析台灣產原料、實驗室製作味噌與市售味噌中植化素含量。在大豆異黃酮與大豆皂素之分析平台能夠測定到16種大豆異黃酮與19種大豆皂素,在大豆原料中異黃酮主要為丙二醯態,經由製成味噌則被微生物代謝為配醣體之形式,同時也產生3’-hydroxygenistein等代謝產物;大豆皂素主要以帶有DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) 基團存在於大豆原料中,DDMP基團會因熱加工而使其掉落形成B group的大豆皂素,然而因其醣基種類複雜,味噌中微生物未能使其醣基結構上有明顯之變化。植物固醇與生育醇之同步分析平台中,能夠偵測到糖苷態、自由態與酯化糖苷態固醇,以及8種生育醇。在大豆原料中植物固醇以自由態為主,而製成味噌微生物中酵素作用後,則以糖苷態固醇為主。大豆經由微生物作用製成味噌後,植化素會產生不同的結構變化,藉由本研究之分析平台能夠作為分析植化素在發酵過程中結構變化之工具。
In addition to proteins and lipids, soybean is a good source of bioactive phytochemicals, i.e. isoflavones, soyasaponins, phytosterols and tocopherols. To effectively evaluate the contents of phytochemicals in Taiwanese soybean cultivars and its fermented product, miso, this research established two simultaneously analytical platforms, one for isoflavones and soysaponins and another for phyosterols and tocopherols using high-performance liquid-chromatography coupled with photodiode array detection (PDA) and tandem mass spectrometry (LC-MS/MS). There were 16 isoflavones and 19 soyasaponins simultaneously analyzed on the first platform. The malonylglucosides were the major isoflavone type of soybean raw material, nevertheless, they were converted into aglycones and metabolites such as 3’-hydroxygenistein by processing and microorganism in miso making. Soyasaponins with DDMP group is the major saponin type in soybean, after heat processing, soyasaponins with DDMP group would be degraded into B group soyasaponins. The second analytical platform simultaneously determined steryl glucosides, free sterols, acylated steryl glucosides and eight tocopherols. Free sterols were the major forms of phytosterols of soybean. The acylated steryl glycosides phytosterols were converted into steryl glycosides instead the free form of phytosterols in miso. The two analytical platforms developed in this study demonstrate to be effective tools to study the biotransformation in fermentation processing.
誌謝 i
摘要 iii
Abstract iv
縮寫表 v
目錄 vi
圖目錄 ix
表目錄 xii
壹、 前言 1
貳、 文獻回顧 2
一、大豆 (Glycine max (L.) Merrill) 與其特徵化合物 2
1.1 大豆異黃酮 2
1.2 大豆皂素 6
1.3 植物固醇 11
1.4 生育醇 14
二、分析大豆特徵化合物 16
2.1 大豆異黃酮 16
2.2 大豆皂素 18
2.3 植物固醇 20
2.4 生育醇 21
參、 研究目的與實驗架構 23
肆、 材料與方法 24
一、實驗材料 24
二、 實驗藥品 26
2.1 標準品 26
2.2 化學藥品 26
三、 實驗儀器 27
3.1 樣品製備及萃取 27
3.2 高效液相層析串聯線性離子阱質譜儀 27
3.3 高效液相層析串聯高解析軌道式質譜儀 (Q-Exactive) 28
四、 實驗方法 29
4.1. 大豆異黃酮與大豆皂素 29
4.1.1 品管樣品 29
4.1.2 樣品萃取 29
4.1.3 高效液相串聯高解析質譜儀分析條件 29
4.2 植物固醇與生育醇 30
4.2.1樣品萃取植物固醇 30
4.2.2 分析條件 30
4.3 統計方法 31
伍、 結果與討論 32
一、建立大豆異黃酮與大豆皂素之同步分析平台 32
1.1 建立逆相層析法分離大豆異黃酮與大豆皂素 32
1.2 大豆異黃酮之偵測 36
1.3 大豆原料與味噌中大豆異黃酮之含量 43
1.4 大豆皂素之偵測 51
1.5 大豆原料與味噌中大豆皂素之含量 73
二、建立植物固醇與生育醇之同步分析平台 76
2.1 建立逆相層析法分離植物固醇與生育醇 76
2.2 植物固醇與生育醇之偵測 79
2.3 大豆、米與味噌中植物固醇含量 84
2.4大豆原料與味噌中生育醇含量 88
三、製成富集 (enriched) 異黃酮之萃取物 89
陸、 結論 93
柒、 參考文獻 94
捌、 附錄 100
一、大豆異黃酮之品質管制圖 100
二、大豆異黃酮代謝產物與大豆皂素Bb離子強度比 103
三、大豆異黃酮與大豆皂素平台質譜設定inclusion list 107
四、樣品中異黃酮各化合物含量 109
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