請用此 Handle URI 來引用此文件：
http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/48179完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 黃青真 | |
| dc.contributor.author | Chin Hsu | en |
| dc.contributor.author | 徐瑨 | zh_TW |
| dc.date.accessioned | 2021-06-15T06:48:09Z | - |
| dc.date.available | 2014-07-06 | |
| dc.date.copyright | 2011-07-06 | |
| dc.date.issued | 2011 | |
| dc.date.submitted | 2011-05-17 | |
| dc.identifier.citation | (1977) Report of the American Institute of Nurtition ad hoc Committee on Standards for Nutritional Studies. J. Nutr. 107, 1340-8.
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Zang C, Liu H, Bertz J, Possinger K, Koeffler HP, Elstner E & Eucker J (2009) Induction of endoplasmic reticulum stress response by TZD18, a novel dual ligand for peroxisome proliferator-activated receptor α/γ, in human breast cancer cells. Mol. Cancer Ther. 8, 2296-307. Zhang J, Guo H, Tian Y, Liu P, Li N, Zhou J & Guo D (2007) Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products. Phytochemistry 68, 2523-30. 王思晴 (2009) 苜宿芽乙酸乙酯萃物中雌激素活性成分之分離純化及其對雌激素依賴型癌細胞和骨骼細胞株之效應, 台灣大學. 吳夢婷 (2008) 數種具植物雌激素活性材料對卵巢剔除鼠代謝症候群及鈣代謝之影響, 臺灣大學. 林甫容 (2002) 以鼠肝癌細胞株 H4IIEC3 初探幾種 PPAR alpha 活化物對維生素 E 代謝產物 alpha-CEHC 生成之影響, 臺灣大學. 洪永瀚 (2008) 苜蓿芽乙酸乙酯萃取物改善 MRL-lpr/lpr 自體免疫鼠病程發展之探討, 臺灣大學. 許婉貞 (2009) 以卵巢剔除小鼠探討數種植物雌激素化合物/萃物之雌激素相關生理活性, 台灣大學. 趙哲毅 (2003) 苦瓜活化過氧化體增殖劑活化受器及改變脂質代謝相關基因之表現, 臺灣大學. 鄭瑋宜 (2007) 山藥具雌激素活性成份之單離與鑑定研究, 臺灣大學. 謝婉郁 (2005) 山苦瓜改善血糖血脂代謝異常之效應探討, 臺灣大學. 鍾誠珠 (2009) 代謝症候群動物模式之評估探討, 臺灣大學. | |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/48179 | - |
| dc.description.abstract | 婦女在停經後因體內雌激素濃度下降，而產生更年期症候群，長期更面臨罹患骨質疏鬆、心血管疾病、代謝症候群之風險增高。許多研究致力於尋找具有雌激素受器選擇性調節劑 (SERM) 功能之植物雌激素，以取代有副作用之賀爾蒙替代療法 (HRT)。我們發現山苦瓜乙酸乙酯萃物之不皂化物區分 (non-saponifiable fraction, NS) 可促進雌激素受器 (Estrogen receptor, ER) 之轉錄活性，暗示山苦瓜可能含有植物雌激素活性成份。本實驗之目的即為探討山苦瓜之植物雌激素效應，並從山苦瓜中純化分離出具有雌激素活性之成份並鑑定其結構，進一步以雌激素依賴型癌細胞，探討其在雌激素相關生理作用中所扮演之可能角色。
先以三週齡剛離乳之母鼠，初探討餵食山苦瓜是否影響雌激素作用之相關生理狀態。將12 隻三週齡剛離乳之母鼠依體重隨機分為 B組 (basal diet，n=4)、E2 組 (2 mg 17β-estradiol/kg diet) 及 BGP 組 (5% 山苦瓜凍乾粉末)。結果發現 E2 組小鼠之陰道開口時間顯著較 B 組提早了 4.5 天 (p<0.01)，而 BGP 組亦提早了 1.8 天 (p = 0.12)。繼以陰道抹片觀察其動情週期的變化，發現 BGP 組小鼠停留於動情期 (Estrus phase) 的時間佔完所有時間之 61%，顯著較 B 組停留於動情期之時間 (41%) 長 (p<0.01)，而 E2 組小鼠則是長期處於動情期 (100%，p<0.01)。 次以卵巢剔除母鼠，餵以高油飼料 (HF 組) 或分別添加 E2、5%山苦瓜凍乾粉末 (BGP 組)、0.2% 不皂化物區分 (NS組) 等飼料15 週或 30 週。結果山苦瓜與 NS 的攝取不會產生如 E2 補充時子宮脹大的效果。餵食實驗飼料三週後進行鈣平衡分析實驗，則觀察到E2 組 (n=5) 糞便鈣排出量較其控制組 (HF 組) 少 (p<0.01)，鈣平衡 (p=0.12) 與鈣保留率 (p=0.07) 則有較高之趨勢。而 BGP 組 (n=5) 亦有糞便鈣與尿鈣排出量較少的現象 (p<0.01)，且 BGP 組與 NS 組之鈣平衡及鈣保留率均提升至與 E2 組沒有顯著差異的效果 (p>0.05)。顯示山苦瓜中成份對缺乏雌激素所引起之骨質疏鬆應有預防保護之功效。乃進一步對其雌激素活性成份進行純化分離如下。 將山苦瓜凍乾粉依序以乙酸乙酯及 95% 酒精萃取，再以開放式管柱層析及製備式 HPLC 分別對乙酸乙酯萃取物之不皂化物區分 (NS) 及酒精萃取物之酸水解產物 (acid-hydrolyzed product, AH) 進行純化分離，並利用ER轉錄活性分析 (transactivation assay) 追蹤活性成份。結果從 NS 中分得葉黃素、loliolide、植醇以及一已知之cucurbitane-type 三萜類化合物5β,19-epoxycucurbita-6,24-dien-3β,23-diol (6)；從 AH 中單離出五個cucurbitane-type 三萜類新化合物，經結構鑑定知其分別為 cucurbita-6,22(E),24-trien-3β-ol-19,5β-olide (1)、 4β,19-epoxycucurbita-6,22(E),24-trien-3β,19-diol (2)、3β-hydroxycucurbita-5(10),6,22(E),24-tetraen-19-al (3)、19-dimethoxycucurbita-5(10),6,22(E),24-tetraen-3β-ol (4) 與 19-nor-cucurbita-5(10),6,8,22(E),24-pentaen-3β-ol (5)。在沒有細胞毒性之濃度處理下，除了化合物 3 與 4，其餘化合物均可活化 ER 轉錄活性。然而相對於輕微活化 ER 的效果，化合物 1、2、3、5與 6 則可以顯著拮抗 E2 所誘發之 ER 轉錄活性。而這些化合物中除了化合物 3 與 4 不具活化 PPARγ 之能力，其他化合物則亦有活化 PPARα與 PPARγ 轉錄活性之效果。 最後以雌激素依賴型乳癌細胞 MCF-7 與子宮內膜癌細胞 Ishikawa 探討山苦瓜區分物及各單離成份之雌激素相關效應。先以 MTT 分析 MCF-7 與 Ishikawa 細胞之增生，結果顯示葉黃素與化合物 2、3、6 可顯著降低 MCF-7之 MTT吸光值。而除了化合物 4 不影響 Ishikawa 之細胞增生，葉黃素及其他五個三萜類化合物均會顯著降低 Ishikawa 之 MTT 吸光值。又在 E2 共同處理下，葉黃素與六個三萜類化合物均可顯著抑制 E2 所誘發之 MCF-7 與 Ishikawa細胞增生，且降低 Ishikawa 細胞內源性 ALP 的活性。而以相同濃度處理非雌激素依賴型癌細胞 MDA-MB-231，則不影響其 MTT 吸光值。 綜之，本研究自酸水解山苦瓜萃物 (AH) 中單離出 5 個新的三萜類化合物，期中 4 個具有植物雌激素活性，另自 NS 中也找到 4 個植物雌激素化合物。這些化合物具有顯著之拮抗雌激素活性。 | zh_TW |
| dc.description.abstract | Postmenopausal women suffer not only from the menopausal syndromes but also higher risks of osteoporosis, cardiovascular diseases and metabolic syndrome. Some phytoestrogens have been characterized as selected estrogen receptor modulator (SERM) and regarded as one of the substitute for hormone-replacement therapy which was shown to have adverse events. The Cucurbitaceae plant Momordica charantia (MC, bitter gourd) is a common tropical vegetable and has been used in traditional medicine. We have found the the non-saponifiable fraction (NS) of a wild bitter gourd (BG) extract activated transcription via estrogen receptors (ER). Studies in this thesis thus aimed at identifying and characterizing phytoestrogenic compounds in BG.
To assess the in vivo estrogen-related response of BG, 3 groups (n=4/group) of weanling C57BL/6J female mice were respectively fed a basal diet (B), basal diet supplemented with E2 (2 mg 17β-estradiol/kg diet) or BGP (5% bitter gourd powder). The vaginal opening of mice treated with E2 and BGP were respectively, 4.5 days (p<0.01) and 1.8 days (p=0.12) earlier than those of the B group. Results of vaginal smear examination indicated that the E2 group persisted on the estrus stage while BGP group showed a prolonged estrus stage (61%) that was longer than B group (41%)(p<0.01). To assess more in vivo estrogen-related response, ovariectomized mice fed a high fat diet (HF group) were supplemented with E2 (E2 group), 5% bitter gourd powder (BGP group) or 0.2% non-saponifiable fraction from ethyl acetate extract of BG (NS group) for 15 or 30 weeks. The uterus weight was significantly higher in the E2 group (p<0.05) but not in the BGP and the NS group. In the calcium balance analysis after 3 weeks feeding, the fecal Ca excretion was less (p<0.01), and the Ca balance (p=0.12) and Ca retention (p=0.07) were higher in the E2 group. The fecal and urinary Ca excretion of the BGP group were also less (p<0.01) than the control group. The Ca balance and Ca retention of BGP and NS groups were also improved and comparable to those of the E2 group (p>0.05). These results implied that BG may be beneficial for estrogen deficiency. To elucidate the phytoestrogenic compounds in BG, a cell-based ER transactivation assay were used to track the active compounds. Lyophilized powders of BG fruits were exhaustively extracted with ethyl acetate (EA) and 95% ethanol (EtOH), sequentially. The non-saponifiable fraction (NS) of the EA extract as well as the acid-hydrolyzed EtOH extract (AH) was fractionated by repeated column chromatography and isolates were further purified by preparative HPLC or RP-HPLC. Lutein, loliolide, phytol, and one known cucurbitane-type triterpenoid 5β,19-epoxycucurbita-6,24-dien-3β,23-diol (6) were identified from NS. Five new cucurbitane-type triterpenoids, cucurbita-6,22(E),24-trien-3β-ol-19,5β-olide (1), 4β,19-epoxycucurbita-6,22(E),24-trien-3β,19-diol (2), 3β-hydroxycucurbita-5(10),6,22(E),24-tetraen-19-al (3), 19-dimethoxycucurbita-5(10),6,22(E),24-tetraen-3β-ol (4), together with 19-nor-cucurbita-5(10),6,8,22(E),24-pentaen-3β-ol (5) were isolated from AH. Except for compound 3 and 4, the remaining compounds showed weak agonistic activity via ERα and β in the non-cytotoxic concentration range. Compounds 1, 2, 3, 5 and 6 showed significant antagonist activity on ERs in the transactivation assay. These ER active extract/compounds were then assessed for their effect on the proliferation of estrogen-dependent human breast cancer cell MCF-7 and endometrial-derived Ishikawa cells by MTT assay in the absence or presence of 1 nM E2. Lutein, compound 2, 3 and 6 significantly reduced the MTT values of MCF-7. Except for compound 4, lutein and the remaining 5 cucurbitane-type triterpenoids significantly reduced the MTT values of Ishikawa cells. All the 6 cucurbitane-type triterpenoids decreased the ER target gene ALP activity of Ishikawa cells. Besides, lutein and all the 6 cucurbitane-type triterpenoids antagonized the proliferation effect of 1 nM E2 in both of these estrogen-dependent cancer cell lines. These inhibition effects were not observed in the estrogen-independent MDA-MB-231 cells within a similar concentration range. In conclusion, five new cucurbitane-type triterpenoids were isolated and identified from the AH of Momordica charantia, and four of them showed estrogenic/antiestrogenic activities. Besides, another four known compounds were isolated and identified from the NS as phytoestrogens of MC. These compounds showed significant antagonistic activity toward E2. These results provide basic evidence that Momordica charantia might be a source of beneficial phytoestrogens isolated and identified. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-15T06:48:09Z (GMT). No. of bitstreams: 1 ntu-100-D93b47304-1.pdf: 8614664 bytes, checksum: b20547fcb339dd18fedc876e760d8fc2 (MD5) Previous issue date: 2011 | en |
| dc.description.tableofcontents | 中文摘要 i
英文摘要 iv 縮寫對照表 vii 第一章 緒論 1 第一節 前言 1 第二節 文獻回顧 1 一、雌激素 1 二、雌激素受器 (estrogen receptor, ER) 2 三、選擇性雌激素受器調節器 (SERM) 5 四、ER subtype-specific ligand binding 7 五、PPAR 與 ER 之關聯研究 8 六、山苦瓜之簡介 11 第三節 研究假說與架構 14 一、研究假說 15 二、實驗設計 15 第二章 山苦瓜對離乳小鼠與卵巢剔除鼠之雌激素效應 16 第一節 前言 16 第二節 材料與方法 17 一、實驗大綱 17 二、動物飼養及卵巢剔除手術 18 三、實驗飼料 19 四、陰道開口時間與抹片觀察 (離乳小鼠實驗) 21 五、口服葡萄糖耐受測試 (Oral glucose tolerance test, OGTT) (卵巢剔除鼠之高油飼料實驗) 22 六、動物犧牲與樣品收集 23 七、血糖與血脂分析 23 八、肝臟過氧化體 Acyl-CoA Oxidase (ACO) 活性分析 (卵巢剔除鼠之高油飼料實驗) 24 九、組織 creatine kinase (CK) 活性分析 (離乳小鼠實驗) 27 十、脂質吸收分析 (卵巢剔除鼠之高油飼料實驗) 28 十一、鈣平衡與骨鈣含量分析 29 十二、統計分析 30 第三節 結果 31 一、離乳小鼠實驗 31 二、卵巢剔除鼠實驗 41 第四節 討論 56 一、雌激素與山苦瓜的攝入對正常母鼠體內生理活性之影響 56 二、雌激素、山苦瓜與不皂化物 (NS) 的攝入對卵巢剔除鼠體內生理活性之影響 58 第五節 結論 60 第三章 山苦瓜活化 ER 成份之純化分離與結構鑑定 61 第一節 前言 61 第二節 材料與方法 61 一、細胞培養與轉錄活性分析 61 二、山苦瓜樣品處理與化學成分分離及鑑定 66 第三節 結果 73 一、山苦瓜不皂化物 NS 對 ER 轉錄活性的影響 73 二、以 GC-MS 初探不皂化物 NS 內已知成份 76 三、山苦瓜不皂化物 NS 經管柱層析之區分活化 ER 轉錄活性之效果 76 四、山苦瓜酒精萃取物與其酸水解產物之 ER 活性分析 81 五、山苦瓜酒精萃物之酵素水解產物之活性分析 82 六、山苦瓜中具 ER 活性成分之純化分離與結構鑑定 84 七、山苦瓜中單一活性成分對 ER 轉錄活性的影響 98 第四節 討論 103 一、單離活性成份之材料製備策略 103 二、山苦瓜中具有 ER 活性之化合物 104 第五節 結論 108 第四章 山苦瓜活化 ER 成份對雌激素依賴型癌細胞之效應 109 第一節 前言 109 第二節 材料與方法 109 一、MCF-7 細胞增生實驗 109 二、Ishikawa 細胞增生與內源性 Alkaline phosphatase (ALP) 活性分析 111 三、MDA-MB-231 細胞存活率實驗 113 第三節 結果 114 一、山苦瓜萃物與活性成分對 MCF-7 細胞增生的影響 114 二、山苦瓜粗萃物與活性成分對Ishikawa細胞增生與內源性 ALP 活性的影響 118 三、山苦瓜中 cucurbitane-type triterpenoids 成分對 MDA-MB-231 細胞存活率的影響 122 四、以 colony formation test 分析山苦瓜區分及活性成份對 MCF-7 細胞增生的影響 124 第四節 討論 125 第五節 結論 127 第五章 山苦瓜活化 ER 成份對 PPAR 轉錄活性的影響 129 第一節 前言 129 第二節 材料與方法 129 第三節 結果 130 第四節 討論 133 第五節 結論 136 第六章 綜合討論與結論 137 第一節 綜合討論 137 第二節 結論 141 第七章 參考文獻 142 附錄 光譜圖 152 | |
| dc.language.iso | zh-TW | |
| dc.subject | 植物雌激素 | zh_TW |
| dc.subject | 雌激素受器 | zh_TW |
| dc.subject | 山苦瓜 | zh_TW |
| dc.subject | 轉錄活性分析 | zh_TW |
| dc.subject | 卵巢剔除鼠 | zh_TW |
| dc.subject | 雌激素依賴型癌細胞 | zh_TW |
| dc.subject | estrogen receptor | en |
| dc.subject | Momordica charantia | en |
| dc.subject | estrogen-dependent carcinoma | en |
| dc.subject | transactivation assay | en |
| dc.subject | ovariectomized mice | en |
| dc.subject | phytoestrogen | en |
| dc.title | 自山苦瓜單離植物雌激素及其化學鑑定與生物活性探討 | zh_TW |
| dc.title | Isolation, Chemical Identification and Biological Characterization of Phytoestrogens from Wild Bitter Gourd (Momordica Charantia) | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 99-2 | |
| dc.description.degree | 博士 | |
| dc.contributor.oralexamcommittee | 郭悅雄,吳文惠,趙蓓敏,嚴孟祿,楊健志,林璧鳳 | |
| dc.subject.keyword | 山苦瓜,雌激素受器,植物雌激素,轉錄活性分析,卵巢剔除鼠,雌激素依賴型癌細胞, | zh_TW |
| dc.subject.keyword | Momordica charantia,estrogen receptor,phytoestrogen,transactivation assay,ovariectomized mice,estrogen-dependent carcinoma, | en |
| dc.relation.page | 181 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2011-05-17 | |
| dc.contributor.author-college | 生命科學院 | zh_TW |
| dc.contributor.author-dept | 生化科技學系 | zh_TW |
| 顯示於系所單位： | 生化科技學系 | |
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