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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 呂廷璋 | |
dc.contributor.author | Chun-Hui Chiu | en |
dc.contributor.author | 邱群惠 | zh_TW |
dc.date.accessioned | 2021-06-16T10:16:13Z | - |
dc.date.available | 2023-12-31 | |
dc.date.copyright | 2013-08-28 | |
dc.date.issued | 2013 | |
dc.date.submitted | 2013-08-18 | |
dc.identifier.citation | 中國藥科大學 (2002). 皂苷類. http://mcn.800idy.com/pharmacognosy/shengyaoxue/san33.htm.
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/60356 | - |
dc.description.abstract | 羅漢果皂苷為一群具有高度甜味的三萜類糖苷分子,已被證實具有調節血糖之生理功能,分子結構上以帶有五個β-D-葡萄糖基的mogroside V是主要天然羅漢果的皂苷形式。由於此類皂苷沒有特殊紫外光及-可見光吸收波長以及含有多種同分異構物,因此在分析上的困難高,本試驗使用液相層析串聯式電灑游離多次質譜 (HPLC/ESI tandem MS) 方法來克服羅漢果皂苷在分析上的困難 。羅漢果皂苷在電灑游離狀態下,以使用0.01% 甲酸修飾劑相較於醋酸、三乙基胺及氨水有最佳的離子穩定度。羅漢果皂苷在離子阱中使用碰撞誘導游離 (CID) 的質譜斷裂模式,可觀察到依序減少葡萄醣基的質譜特徵,配合管柱的滯留時間,所獲得分子結構資訊可做為定性分析的依據。Mogroside V在市售羅漢果乾燥果實與濃縮萃取粉末產品中的含量分別為1.5~1.8與25.9%。另外分析7種宣稱含羅漢果之加工產品的含量範圍為0.3~1.8%,其中有一種膏狀飲品與二種糖果未檢出有羅漢果苷。
為選擇性的轉換mogroside V為其他較少醣基數目的皂苷型態,於靈芝菌絲培養液中添加羅漢果水萃液,可顯著的增加菌絲生長;即使在只含羅漢果水萃液,而無其他營養的情況下,21天後靈芝菌絲生長量也與培養於麥芽萃取物培養基之控制組無顯著差異。顯示靈芝菌絲可利用β-glucosidase水解mogroside V結構上的葡萄糖,主要轉換成帶有三個葡萄糖基的mogroside IIIE;當環境中缺乏碳源時,靈芝菌絲則會進一步的利用mogroside IIIE上的葡萄糖基,轉成帶有二個葡萄糖基的mogroside II A,而mogroside IIA分子上所帶之β-(1,2) 鍵結的葡萄糖基對靈芝菌絲所分泌的β-glucosidase有較強的耐受性。進一步利用酵母菌 (Saccharomyces cerevisiae) 探討對羅漢果皂苷上醣基型態之轉換機制實驗中,顯示野生型 (wild type) 酵母菌可將羅漢果皂苷萃取物進行生物轉換,將mogroside V的羅漢果皂苷轉換產生具四醣及三醣的羅漢果皂苷,siamenoside I、mogroside IV及mogroside IIIE。為進一步了解酵母菌中主要轉換羅漢果皂苷之葡萄糖水解酵素,利用酵母菌單一非必需基因 (non-essential gene) 剔除突變基因庫 (deletion sets),篩選出exg1Δ及kre6Δ可影響羅漢果皂苷降解途徑,其中kre6Δ酵母菌突變菌株可快速產生較高專一性之羅漢果皂苷mogroside IIIE;而Exg1則具有選擇性水解羅漢果皂苷之β-1, 6-葡萄糖鍵結的能力。本論文利用HPLC/ESI tandem MS開發一個可例行性檢測羅漢果皂苷分子的分析,利用此分法觀察到靈芝與酵母菌的β-glucosidase對羅漢果皂苷分子上醣基的水解具有選擇性,可應用為製備不同醣苷型態的方法。 | zh_TW |
dc.description.abstract | The sweetness of Siraitia grosvenori fruit comes from a mixture of cucurbitane-type triterpene saponins, mogrosides I-V. mogroside V, a triterpene pentaglycoside,is the major component of mogrosides.A HPLC-electrospray ionization- tandem mass spectrometry (MSn) was established to analyze contents of mogrosides, compounds without UV-absorption, in S. grosvenorii containing products. Using 0.01% of formic acid affiliated the ionization of mogroside on electrospray interface. It is a superior modifier to acetic acid, triethylamine, and ammonia. The mogroside V molecule sequentially lost its glucosyl unit as the mass spectrometry being operated at collision-induced dissociation mode. This fragmentation pattern provided structural information to identify the compound in addition to retention time on column and the molecular weight. The dried fruit purchased at Chinese herb store in Taipei had morgroside content about 1.5%. The content of an extract powder was 25.6% which was the highest value among the selected commercial samples. Most of examined products contained mogroside V in the range of 0.3~1.8%, whereas some candy and syrup products could not find any contents.
The purpose of this study was to investigate the structural modification of mogrosides by Ganoderma lucidum mycelium and yeast. During the growth of the G. lucidum, the mycelium showed significant activity of beta-glucosidase and able to hydrolyze the glucosyl residues of mogroside V. Adding water extract of the fruit did not impact the growth of mycelia in a malt extract medium. The major metabolite of mogroside was tritepene triglucoside, mogroside IIIE. The mycelia of G. lucidum were able to further utilize one glucosyl residue on Mogroside IIIE and converted it to triterpene diglycoside, Morgroside II A when the carbon source was limited. According the results of high-performance liquid chromatography coupled withelectrospray ionization tandem mass spectrometry, the beta-(1,2) linkage of glucosyl were more resistant to hydrolysis of beta-glucosidase of G. lucidum. In the last part of this research, we attempt to selectively convert the major saponin mogroside V, a mogrol pentaglucoside, into mogroside III E, a triglucoside, via the beta-glucosidases of the budding yeast Saccharomyces cerevisiae. We report that the beta-glucopyranosyl and beta-glucopyranosyl-(1,2)-beta-D- glucopyranosyl attached on C-3 and -24 of mogrol, respectively, were resistant to hydrolysis by yeast beta-D-glucosidases. We further screened 16 mutants bearing single defective glucanase or glucosidase genes, thereby demonstrating that Exg1 is a major enzyme of the initiation of mogroside V conversion. Deletion of the KRE6 gene unexpectedly facilitated the production of mogroside III E in yeast culture. This paper demonstrates that yeast knockout mutants are a valuable tool for saponin modification and for studying the specificity of glucosidase function. | en |
dc.description.provenance | Made available in DSpace on 2021-06-16T10:16:13Z (GMT). No. of bitstreams: 1 ntu-102-D96641004-1.pdf: 3262980 bytes, checksum: 58afd1f425309010695b61eeed406e03 (MD5) Previous issue date: 2013 | en |
dc.description.tableofcontents | 壹、前言 1
貳、文獻回顧 2 第一章、皂素 (saponins) 2 1.1 定義 2 1.2 來源 2 1.3 非醣基 (aglycone) 之分類 2 1.3.1 三萜之分類 3 1.3.2 固醇之分類 6 1.3.3 固醇生物鹼之分類 7 1.4 醣基 (glycine) 之特徵 8 1.5 三萜之分析方法 11 1.5.1羅漢果皂苷 12 1.5.2靈芝酸 15 第二章、羅漢果Siraitia grosvenorii 16 2.1 安全性評估 16 2.1.1 急性口服試驗 17 2.1.2 亞急性口服試驗 17 2.1.3 亞慢性口服試驗 19 2.1.4 基因毒性試驗 19 2.1.5 人體試驗 20 2.2 羅漢果皂苷 (Mogrosides) 化學結構 21 2.3 羅漢果皂苷的生物合成 24 2.3.1 甲二羥戊酸途徑 (mevalonic acid pathway, MVA) 24 2.3.2 甲基赤藻糖醇磷酸化途徑 (2C-methyl-D-erythritol-4-phosphate pathway, MEP) 25 2.3.3 三萜的環化 25 2.4 羅漢果皂苷含量及甜味性質 28 2.5 羅漢果皂苷之生理活性 30 2.5.1 抗糖尿病 30 2.5.2 抗致癌性 31 2.5.3 抗氧化能力 31 2.5.4 抗發炎反應 (anti-inflammatory effect) 32 2.5.5 對人類皰疹病毒第四型(Epstein-Barr Virus, EBV) 的抑制 32 2.6 羅漢果皂苷之生物轉換 35 第三章、靈芝及酵母菌 38 3.1 靈芝 (Ganoderma lucidum) 38 3.2 靈芝酸 38 3.3 酵母菌 40 3.4 酵母菌相關之β-glucosidase基因 40 參、研究目的與實驗架構 41 第一章、研究目的 41 第二章、實驗架構 42 第一部分:以液相層析串聯質譜儀分析羅漢果皂苷與市售商品含量之檢驗 43 第一章、研究目的 43 第二章、實驗設計 43 第三章、材料與方法 44 3.1 試驗器材 44 3.1.1 實驗材料 44 3.1.2 標準品及實驗藥品 44 3.2 儀器設備 44 3.2.1 層析耗材 44 3.2.2 儀器設備 45 3.3 實驗方法 45 3.3.1 羅漢果皂苷之液相層析串聯質譜分析 45 3.3.2 市售羅漢果樣品分析Mogroside V含量 48 3.3.3 統計分析 48 第四章、結果與討論 49 4.1 羅漢果皂苷之液相層析串聯質譜分析 49 4.1.1 探討不同電壓及溫度對羅漢果皂苷游離化之影響 49 4.1.2 修飾劑 (modifier, Formic acid, Acetic acid, Ammonia, Triehtylamine) 對MG V游離化之影響 59 4.1.3 游離條件最佳化設定 65 4.1.4 以多次質譜對羅漢果皂苷進行斷裂片斷分析 65 4.1.5 高效能液相層析串聯質譜之設定 71 4.1.6 高相能液相層析串聯質譜分析線性範圍、偵測極限與檢量線製作 71 4.1.7 添加回收 (spike) 試驗 74 4.2 市售樣品分析 74 第五章、結論 77 第二部分:利用靈芝菌絲對羅漢果皂苷進行生物轉換 78 第一章、研究目的 78 第二章、實驗架構 79 第三章、材料與方法 80 3.1 試驗器材 80 3.1.1 實驗材料 80 3.1.2 標準品及實驗藥品 80 3.1.3 培養基材料 81 3.2 儀器設備 81 3.2.1 層析耗材 81 3.2.2 儀器設備 81 3.2.3 高效液相層析系統 81 3.3 實驗方法 82 3.3.1 菌株的培養 82 3.3.2 分析項目與方法 83 第四章、結果與討論 88 4.1 發酵期間葡萄糖含量之影響 88 4.2 羅漢果水萃液對靈芝菌絲之影響 90 4.2.1 靈芝菌絲體之乾重 (g) 90 4.2.2 菌絲球之直徑 (cm) 91 4.2.3 pH值 94 4.3 靈芝菌絲對羅漢果皂苷之生物轉化 96 4.3.1 羅漢果皂苷Mogrosides之生物轉化 96 4.3.2 發酵期間2%L+M組之羅漢果皂苷變化 100 4.3.3 發酵期間1%L+M組之羅漢果皂苷變化 101 4.3.4 發酵期間2% L組之羅漢果皂苷變化 106 4.3.5 發酵期間1%L組之羅漢果皂苷變化 106 4.3.6 靈芝菌絲對羅漢果皂苷MG IIIE及MG IIA之生成率 112 4.4 靈芝轉化羅漢果皂苷MG IIIE及MG IIA之製備 113 4.4.1 羅漢果靈芝發酵物之Diaion HP-20管柱層析 113 4.4.2 靈芝轉化羅漢果皂苷之核磁共振分析 113 4.5 靈芝菌絲對羅漢果皂苷的轉化途徑 126 4.6 β-葡萄糖苷酶 (β-glucosidase) 活性變化 128 4.7 靈芝酸 129 第五章、結論 134 第三部分:利用酵母菌對羅漢果皂苷進行生物轉換 135 第一章、研究目的 135 第二章、實驗架構 136 第三章、材料與方法 137 3.1 試驗器材 137 3.1.1 實驗材料 137 3.1.2 標準品及實驗藥品 137 3.1.3 培養基材料 137 3.2 儀器設備 137 3.3 實驗方法 137 3.3.1 酵母菌培養基之配製 137 3.3.2 酵母菌株的培養與保存 138 3.3.3 羅漢果皂苷萃液對酵母菌生長的影響 138 3.3.4 酵母菌對羅漢果皂苷萃取物的轉換 139 3.3.5 剔除基因變異株酵母菌轉換羅漢果皂苷 139 3.3.6 補償試驗 (Complementation assay) 139 3.3.7 利用轉形細胞發酵羅漢果萃取溶液 146 第四章、結果與討論 147 4.1 不同濃度羅漢果萃取物 (LHK extracts) 對酵母菌的生長影響 147 4.2 酵母菌生物轉換羅漢果皂苷之探討 150 4.2.1 野生型酵母菌對羅漢果皂苷之生物轉換 150 4.2.2 單一剔除基因酵母菌對羅漢果皂苷之生物轉換影響 150 4.2.3 酵母菌對羅漢果皂苷之轉換效率 161 第五章、結論 167 肆、參考文獻 168 伍、附錄 185 | |
dc.language.iso | zh-TW | |
dc.title | 羅漢果皂苷分析與利用靈芝及酵母菌對其進行生物轉換 | zh_TW |
dc.title | Mogroside determination and its bioconversion by Ganoderma lucidum and Saccharomyces cerevisiae | en |
dc.type | Thesis | |
dc.date.schoolyear | 101-2 | |
dc.description.degree | 博士 | |
dc.contributor.coadvisor | 羅翊禎 | |
dc.contributor.oralexamcommittee | 朱燕華,魏國晉,沈偉強,鄭光成 | |
dc.subject.keyword | 羅漢果皂苷,靈芝,酵母菌,生物轉換,液相層析串聯式電灑游離多次質譜, | zh_TW |
dc.subject.keyword | mogrosides,Ganoderma lucidum,Saccharomyces cerevisiae,biotransformation,HPLC/ESI tandem MS, | en |
dc.relation.page | 199 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2013-08-18 | |
dc.contributor.author-college | 生物資源暨農學院 | zh_TW |
dc.contributor.author-dept | 食品科技研究所 | zh_TW |
顯示於系所單位: | 食品科技研究所 |
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