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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 蘇南維(Nan-Wei Su) | |
dc.contributor.author | Chen Hsu | en |
dc.contributor.author | 許宸 | zh_TW |
dc.date.accessioned | 2021-06-08T00:58:10Z | - |
dc.date.copyright | 2015-02-05 | |
dc.date.issued | 2015 | |
dc.date.submitted | 2015-02-03 | |
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/18289 | - |
dc.description.abstract | 存在於黃豆中的異黃酮(isoflavones)是黃豆的二級代謝物,其化學結構與人體雌激素的雌二醇(estradiol)相似,具有雌激素活性,被認為是植物雌激素(phytoestrogen)。異黃酮依化學結構可分成四大類: malonyl-glucosides、acetyl-glucosides、glucosides和aglycones。在此四大類中,aglycones被認為生理活性最佳,因此許多研究致力於將帶有醣基形態的異黃酮經由去醣基作用(deglycosylation)而轉換成aglycones。近年來,許多文獻指出aglycones的daidzein和genistein具有預防骨質疏鬆、心血管疾病、乳癌及前列腺癌等生理活性。然而,根據Merck Index及眾多文獻記載,daidzein和genistein幾乎不溶於水,生物可利用率(bioavailability)亦不佳。本研究室先前自市售納豆產品中篩選出B. subtilis BCRC 80517,可將glucosides轉換成aglycones,再轉換成水溶性高的代謝物。本論文以此為基礎,進行後續的研究。
第一部分探討B. subtilis BCRC 80517對不同種類異黃酮之生物轉換與代謝途徑。結果發現BCRC 80517可將aglycone (daidzein和genistein)及glucosides (daidzin和genistin)轉換成daidzein 7-O-phosphate (D7P)和genistein 7-O-phosphate (G7P),且BCRC 80517對genistein和genistin的生物轉換率皆大於daidzein和daidzin;malonyl-glucosides則會經由去醣基作用產生aglycones,卻無法進一步被磷酸化。BCRC 80517對異黃酮的生物轉換過程中,大部分的daidzein和genistein被磷酸化生成D7P和G7P,伴隨著微量的daidzein 4’-O-phosphate和genistein 4’-O-phosphate產生。同時,少部分的aglycones也會被醣基化生成glucosides,再進一步轉換成sucinnyl-glucosides。 第二部分探討B. subtilis BCRC 80517生產異黃酮磷酸酯之最適培養條件。結果顯示,BCRC 80517生產異黃酮磷酸酯的最適生產培養基為2% (w/v) sucrose,1% (w/v) (NH4)2HPO4,1.5% (w/v) K2HPO4/KH2PO4 (pH 7.0),0.05% (w/v) MgSO4•7H2O和0.025% (w/v) MnSO4•H2O;最適培養條件為接種5% (v/v)種菌,同時投入2 g/L (1.2 mM daidzein, 2.1 mM genistein)生物轉換基質至生產培養基,於37℃,150 rpm以Hinton’s flask振盪培養48小時後,D7P和G7P生成濃度為0.9 mM和2.0 mM,達到最高生物轉換率,分別為80%和97%。上述培養液經離心除菌、乙酸乙酯萃取、濃縮、正己烷沉澱、HP-20疏水性樹脂層析、濃縮和凍乾後,可得異黃酮磷酸酯混合物,純度為83% (29% D7P, 54% G7P),回收率為94%。D7P和G7P在25℃純水中的溶解度分別為17.9%和10%,比daidzein和genistein的溶解度提高10萬倍之多。 第三部分首先建立測定磷酸化酵素活性的分析方法,再由B. subtilis BCRC 80517的菌體分離與純化出異黃酮磷酸酯合成酶(Isoflavone phosphate synthetase, IFPS)。IFPS屬於胞內酵素,且不會因菌體與異黃酮共培養而使酵素表現量增加。將菌體破菌、離心並收集上清液作為粗酵素液,經硫酸銨沉澱(飽和度40-60%)、DEAE FF、Q HP陰離子交換層析、Phenyl HP疏水性層析及Superdex 75膠體過濾層析等分離純化步驟後,IFPS比活性為128 unit/mg,活性回收率為0.11%,酵素純化倍率為183倍。SDS-PAGE和LC-MS/MS分析純化後之酵素,發現IFPS有839個胺基酸,分子量為95.4 kDa,pI值為4.86,酵素分類為EC 2.7.9.x。IFPS只能以ATP作為磷酸根轉移之來源,Mg2+和Mn2+存在時,酵素才有活性;酵素最適反應溫度為40℃,最適反應pH為7.5,酵素在40℃以下或pH值中性(pH 6.5-8.5)靜置一小時,可維持80%以上酵素活性。 | zh_TW |
dc.description.abstract | Isoflavones are a group of plant secondary metabolites that occur mostly in the subfamily Papilionoideae of the Leguminosae. Soybean (Glycine max) is the most abundant source of isoflavones. To date, 12 natural isoflavones have been found in soybeans, consisting of 3 types of isoflavone aglycones (namely daidzein, genistein and glycitein), and their corresponding conjugates with glucose, acetylglucose and malonylglucose. Due to the similarity of chemical structure between the metabolites of isoflavone and human estrogen-estradiol, daidzein and genistein were found to bind to estrogen receptors. Therefore, aglyconic forms of soy isoflavones are commonly referred to as phytoestrogens and bioactive isoflavones. Hence, most of the relevant studies were devoted to the conversion of glucosidesinto their corresponding aglycones. Recent studies indicated that isoflavones may have health benefits such as prevention of breast cancer, prostate cancer, decreasing the risk of cardiovascular diseases, increasing bone mass density to prevent osteoporosis and reducing menopause symptoms. However, according to the Merck Index and literatures, aglycones are partically water insoluble and show poor bioavailability as well. In previous study, we isolated an FC-10 strain from commercial natto products, which can convert glucosides into their corresponding aglycones, and then further convert them into two unknown metabolites with higher polarity.
In the first part of this thesis, we generated two water soluble isoflavone derivatives, daidzein 7-O-phosphate (D7P) and genistein 7-O-phosphate (G7P), by incubating Bacillus substilis BCRC 80517 with daidzein and genistein. These two isoflavone derivatives were characterized by HPLC-ESI-MS/MS, 13C NMR and 31P NMR. Genistein was found to be phosphorylated more rapidly than daidzein. In addition, this bacterial strain could transform glucosides via aglucones into the corresponding 7-O-phosphate conjugates. However, BCRC 80517 could not transform malonyl glucosides into 7-O-phosphate conjugates. We concluded that during the bioconversion of aglycones, daidzein and genistein were predominantly phosphorylated into D7P and G7P, respectively, meanwhile, a small amount of daidzein 4’-O-phosphate and genistein 4’-O-phosphate were also generated by BCRC 80517. In addition, small amount of aglycones were glycosylated into glucosides, respectively, and were then further converted into 6’’-O-succinyl-glucosides. In the second part of this thesis, we investigated the optimal production medium and culture condition of biotransformation for the production of isoflavone phosphate conjugates by BCRC 80517. The optimal composition of production medium was composed of 2% (w/v) sucrose, 1% (w/v) (NH4)2HPO4, 1.5% (w/v) K2HPO4/KH2PO4 (pH 7.0), 0.05% (w/v) MgSO4•7H2O and 0.025% (w/v) MnSO4•H2O with 2 g/L (1.2 mM daidzein, 2.1 mM genistein) isoflavone substrates. The optimal culture condition was that BCRC 80517 was cultivated with inoculum size of 5% (v/v) seed culture, at 37℃ and 150 rpm in a 500-mL Hinton’s flask containing 100 mL production medium. At the end of 48 h incubation, the bioconversion rates of daidzein and genistein were 80% and 97%, respectively, and the concentration of D7P and G7P in the harvested broth were 0.9 mM and 2.0 mM, respectively. Moreover, the process for recovering D7P and G7P from the culture broth was also investigated in this work. After remove the biomass by centrifugation, supernatant was extracted with an equal volume of ethyl acetate by 4 times, and then n-hexane was added to make the precipitation out of D7P and G7P from the solvent. The precipitate was then dissolved by a small amount of water and further purified with HP-20 resin. The purity and recovery of purified products containing isoflavone phosphate conjugates were 83% (29% D7P, 54% G7P) and 94%, respectively. The water solubility at 25℃ of D7P and G7P were 17.9% and 10%, respectively. Both of the water solubility of these two phosphorylated isoflavone were 100,000-fold higher than their corresponding aglycones. The third part of this thesis is to purify and characterize the biochemical properties of the enzyme acting on the isoflavone phosphorylation. An enzyme assay was developed firstly, and then, the enzyme assay-guided protein purification was conducted to obtain the purified isoflavone phosphate synthetase (IFPS) from BCRC 80517. As a result, the IFPS is an intracellular and constitutent enzyme of BCRC 80517. The enzyme was purified to homogeneity through ammonium sulfate fractionation, DEAE FF, Q HP anion-exchange chromatography, Phenyl HP hydrophobic interaction chromatography and Superdex 75 gel filtration chromatography with the enzyme activity recovery of 0.11% and a 183-fold purification efficiency. The purified isoflavone phosphate synthetase exhibited a specific activity of 128 unit/mg. The molecular mass of IFPS was estimated around 90 kDa by gel filtration and 95 kDa by SDS-PAGE. The protein sequence was identified by LC-MS/MS, which showed that this enzyme contained 839 amino acids, and has a molecular mass was 95.4 kDa with a theoretical pI value was 4.86. This novel enzyme is is categorized into EC 2.7.9.x.The IFPS can use only ATP as the phosphate donor, and Mg2+ is a dominant factor on the activity rather than Mn2+. The optimal conditions for temperature and pH were 7.5 and 40℃ on the activity, respectively. The enzyme was stable in the pH range of 6.5-8.5 with the temperature lower than 40℃. | en |
dc.description.provenance | Made available in DSpace on 2021-06-08T00:58:10Z (GMT). No. of bitstreams: 1 ntu-104-R01623010-1.pdf: 11756401 bytes, checksum: 85a281a3872fbf35bde0147f5df8c55a (MD5) Previous issue date: 2015 | en |
dc.description.tableofcontents | 口試委員會審定書
誌謝 I 中文摘要 IV Abstract VI 縮寫對照表 IX 目錄 XII 圖目錄 XX 表目錄 XXIV 附錄 XXV 第一章 前言 1 第二章 文獻回顧 3 第一節 大豆異黃酮 3 1. 大豆簡介 3 2. 類黃酮簡介 3 3. 植物性雌激素 4 4. 異黃酮之化學結構與生理活性 4 第二節 異黃酮之生物可利用率 11 1. BCS分類系統 11 2. 異黃酮之吸收與代謝 11 3. 異黃酮於人體之口服生物可利用率 12 第三節 異黃酮之微生物轉換 20 1. 類黃酮之微生物轉換 20 2. 異黃酮之微生物轉換 21 2-1 去醣基化 21 2-2 羥基化 21 2-3 醣基化 22 2-4 琥珀酰化 23 2-5 甲基化 23 2-6 氯化 23 2-7 磷酸化 23 第四節 前驅藥物 29 1. 前驅藥物定義與介紹 29 2. 磷酸酯前驅藥物 29 第五節 磷酸化酵素 36 1. 胺基醣苷類抗生素磷酸轉移酶 37 2. 磷酸苯酯合成酶 38 第三章 B. subtilis BCRC 80517對不同種類異黃酮之生物轉換與代謝途徑之探討 44 實驗大綱 45 第一節 材料與方法 46 1. 實驗材料 46 1-1 菌株 46 1-2 不同種類之異黃酮 46 1-3 培養基 47 1-4 試藥與溶劑 47 1-5 實驗儀器設備 48 2. 實驗方法 49 2-1 B. subtilis BCRC 80517對異黃酮之生物轉換 49 2-1-1 種菌之培養 49 2-1-2 不同種類異黃酮之生物轉換 49 2-2分離與純化培養液中的異黃酮生物轉換代謝物 49 2-3 高效液相層析儀分析異黃酮之條件 50 2-4 異黃酮含量之計算 52 2-5 異黃酮磷酸酯生物轉換率之計算方式 53 2-6 高效液相層析串聯式質譜儀分析異黃酮代謝物之條件 53 2-7 核磁共振光譜分析異黃酮衍生物之條件條件 53 第二節 結果與討論 54 1. B. subtilis BCRC 80517對異黃酮生物轉換之發現 54 2. 生物轉換代謝物之結構鑑定 54 2-1 生物轉換代謝物之光譜資訊 55 3. B. subtilis BCRC 80517對不同種類異黃酮之生物轉換 59 3-1 B. subtilis BCRC 80517對aglycones之生物轉換 59 3-2 B. subtilis BCRC 80517對glucosides之生物轉換 60 3-3 B. subtilis BCRC 80517對malonyl-glucosides之生物轉換 60 4. B. subtilis BCRC 80517對異黃酮之生物轉換代謝物分析 66 5. B. subtilis BCRC 80517對異黃酮之代謝途徑 74 第四章 B. subtilis BCRC 80517生產異黃酮磷酸酯之最適培養條件探討 76 實驗大綱 77 第一節 材料與方法 78 1. 實驗材料 78 1-1 菌株 78 1-2 異黃酮 78 1-3 培養基 78 1-4 試藥與溶劑 79 1-5 實驗儀器設備 80 2. 實驗方法 81 2-1 種菌之培養 81 2-2 生產異黃酮磷酸酯之最適培養條件探討 81 2-3 不同菌株生長時期投入基質對生產異黃酮磷酸酯之影響 81 2-4 接種不同種菌體積對生產異黃酮磷酸酯之影響 81 2-5 不同碳源與氮源對生產異黃酮磷酸酯之影響 82 2-6 碳源與氮源濃度對生產異黃酮磷酸酯之影響 82 2-7 無機鹽類對生產異黃酮磷酸酯之影響 82 2-7-1 磷酸鹽濃度 82 2-7-2鎂離子濃度 83 2-7-3 錳離子濃度 83 2-8 生物轉換基質濃度對生產異黃酮磷酸酯之影響 83 2-9 發酵槽培養 84 2-10分離與純化發酵液中的異黃酮磷酸酯 84 2-10-1 異黃酮磷酸酯之萃取 84 2-10-2 利用正己烷進行沉澱 84 2-10-3 HP-20疏水性樹脂層析 84 2-10-4 以半製備級高效液相層析儀之純化D7P和G7P 85 2-10-5 半製備級高效液相層析儀分離異黃酮磷酸酯之條件 85 2-11 以單一的異黃酮基質生產D7P與G7P 85 2-12 異黃酮磷酸酯之溶解度測定 86 2-13 微生物數量之計數 86 2-14 高效液相層析儀分析異黃酮之條件 86 2-15 異黃酮含量及生物轉換率之計算方式 86 2-16 異黃酮磷酸酯生物轉換率之計算方式 86 2-17 統計分析方法 87 第二節 結果與討論 88 1. 不同菌株生長時期投入基質對生產異黃酮磷酸酯之影響 88 1-1 B. subtilis BCRC 80517在NB之生長曲線 88 1-2 B. subtilis BCRC 80517在基礎培養基之生長曲線 88 1-3 不同生長時期投入基質對生產異黃酮磷酸酯之影響 90 2. 接種不同種菌體積對生產異黃酮磷酸酯之影響 92 3. 不同碳源與氮源對生產異黃酮磷酸酯之影響 94 4. 碳源與氮源濃度對生產異黃酮磷酸酯之影響 97 5. 無機鹽類對生產異黃酮磷酸酯之影響 100 5-1 磷酸鹽濃度 100 5-2鎂離子濃度 102 5-3 錳離子濃度 102 6. 生物轉換基質濃度對生產異黃酮磷酸酯之影響 105 7. 利用Hinton’s flask振盪培養生產異黃酮磷酸酯 107 8. 利用3公升發酵槽生產異黃酮磷酸酯 110 9. 培養液中異黃酮磷酸酯的回收程序 112 10. 各別異黃酮磷酸酯標準品之製備 113 10-1 以半製備級高效液相層析儀分離D7P與G7P 113 10-2 以單一的異黃酮基質生產異黃酮磷酸酯 114 11. 異黃酮磷酸酯之溶解度 119 第五章 B. subtilis BCRC 80517異黃酮磷酸酯合成酶之分離純化與特性之探討 120 實驗大綱 121 第一節 材料與方法 122 1. 實驗材料 122 1-1 菌株 122 1-2 培養基 122 1-3 緩衝液 123 1-4 試藥與溶劑 124 1-5 實驗儀器設備 126 2. 實驗方法 127 2-1 酵素活性測定 127 2-2 異黃酮磷酸酯合成酶之分離純化 127 2-2-1 菌株之活化與菌體培養 127 2-2-2 菌體破菌 127 2-2-3 硫酸銨沉澱 128 2-2-4 DEAE Sepharose陰離子交換層析 128 2-2-5 第一次Q Sepharose陰離子交換樹脂層析 128 2-2-6 第二次Q Sepharose陰離子交換樹脂層析 129 2-2-7 Phenyl Sepharose疏水性層析 129 2-2-8 Superdex 75膠體過濾層析 129 2-3 蛋白質電泳分析 130 2-3-1 SDS-PAGE電泳分析 130 2-3-2 Native-PAGE電泳分析 130 2-3-3 蛋白質銀染 130 2-4 蛋白質定量方法 130 2-5 蛋白質質譜分析 131 2-5-1 樣品前處理 131 2-5-2 LC-MS/MS之分析條件 131 2-6 異黃酮磷酸酯合成酶之特性分析 132 2-6-1 核苷三磷酸對異黃酮磷酸酯合成酶之影響 132 2-6-2 二價金屬離子對異黃酮磷酸酯合成酶之影響 132 2-6-3 異黃酮磷酸酯合成酶之最適溫度及最適pH 132 2-6-4 異黃酮磷酸酯合成酶之溫度及pH穩定性 133 2-7 高效液相層析儀分析條件 134 2-7-1 高效液相層析儀分析genistein與G7P條件 134 2-7-2 高效液相層析儀分析類黃酮之條件 135 2-7-3質譜儀分析類黃酮衍生物之條件 135 第二節 結果與討論 136 1. 異黃酮磷酸酯合成酶之分離純化 136 1-1 建立異黃酮磷酸酯合成酶活性測定方法 136 1-1-1 酵素反應液之配製與酵素活性之測定方法 137 1-1-2 酵素分泌位置與分布 138 1-1-3 酵素活性之測定 138 1-1-4 菌體與異黃酮共培養之異黃酮磷酸酯合成酶活性 144 1-2 異黃酮磷酸酯合成酶之分離純化 145 1-2-1 硫酸銨沉澱 145 1-2-2 DEAE Sepharose陰離子交換層析 145 1-2-3 Q Sepharose陰離子交換樹脂層析 (第一次) 146 1-2-4 Q Sepharose陰離子交換樹脂層析 (第二次) 146 1-2-5 Phenyl Sepharose疏水性層析 146 1-2-6 Superdex 75膠體過濾層析 147 1-2-7 蛋白質電泳分析 152 1-2-8 酵素純化表 153 1-2-9 蛋白質質譜分析 157 1-2-10 蛋白質序列分析 158 1-2-11 蛋白質序列比對 166 1-2-12 Protein 1與phenylphosphate synthase胺基酸序列比較 169 2. 異黃酮磷酸酯合成酶特性分析 171 2-1核苷三磷酸和二價金屬離子對酵素活性之影響 171 2-2 異黃酮磷酸酯合成酶之最適溫度及最適pH 171 2-3 異黃酮磷酸酯合成酶之溫度及pH穩定性 172 第六章 結論 176 一、B. subtilis BCRC 80517對異黃酮之生物轉換與代謝途徑之探討 176 二、B. subtilis BCRC 80517生產異黃酮磷酸酯之最適培養條件探討 176 三、B. subtilis BCRC 80517異黃酮磷酸酯合成酶之分離純化與特性之探討 177 第七章 參考文獻 178 附錄 190 | |
dc.language.iso | zh-TW | |
dc.title | 枯草桿菌BCRC 80517對大豆異黃酮生物轉換之研究 | zh_TW |
dc.title | Studies on the Biotransformation of Soy Isoflavone by Bacillus subtilis BCRC 80517 | en |
dc.type | Thesis | |
dc.date.schoolyear | 103-1 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 李敏雄(Min-Hsiung Lee),陳錦樹(Chin-Shuh Chen),蔡國珍(Guo-Jane Tsai),張世宗(Shih-Chung Chang) | |
dc.subject.keyword | 納豆菌,異黃酮,生物轉換,異黃酮磷酸酯,異黃酮磷酸酯合成?, | zh_TW |
dc.subject.keyword | Bacillus subtilis,isoflavone,biotransformation,daidzein 7-O-phosphate,genistein 7-O-phosphate,isoflavone phosphate synthetase, | en |
dc.relation.page | 196 | |
dc.rights.note | 未授權 | |
dc.date.accepted | 2015-02-03 | |
dc.contributor.author-college | 生物資源暨農學院 | zh_TW |
dc.contributor.author-dept | 農業化學研究所 | zh_TW |
顯示於系所單位: | 農業化學系 |
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