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http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/51038完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 李水盛 | |
| dc.contributor.author | Yi-Li Lin | en |
| dc.contributor.author | 林義力 | zh_TW |
| dc.date.accessioned | 2021-06-15T13:24:13Z | - |
| dc.date.available | 2021-08-26 | |
| dc.date.copyright | 2016-08-26 | |
| dc.date.issued | 2016 | |
| dc.date.submitted | 2016-06-20 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/51038 | - |
| dc.description.abstract | 第一部份 香苦草抑制黃嘌呤氧化酶活性成分之研究
痛風是一種由尿酸結晶堆積於關節而造成的代謝性疾病；其中，黃嘌呤氧化酶在尿酸的形成中扮演很重要的角色，故臨床上常使用其抑制劑allopurinol來做為長期治療的用藥。然而，此藥物可能引發嚴重的過敏反應Stevens-Johnson syndrome，所以找尋治療痛風的替代藥物仍屬必須。根據本實驗室過去的研究，頭花香苦草(Hyptis rhomboids)中具有抑制黃嘌呤氧化酶的成分。因此，本研究旨在探索同屬物種的香苦草(H. suaveolens)中是否同樣具有抑制黃嘌呤氧化酶的成分。 香苦草莖部的乙醇萃取物經極性切割後劃分為二氯甲烷、乙酸乙酯、正丁醇和水可溶部分，再進一步對活性較佳的乙酸乙酯和正丁醇可溶部分進行分離。過程中使用Sephadex LH-20、silica gel和逆相層析管柱、離心式分配層析，以及半製備HPLC等，共計得到17個化合物，經由核磁共振光譜及質譜技術分析確認dimethyl melitrate A (9)和9'-O-methyl melitrate A (10)為新的化合物。其餘15個化合物為ursolic acid (1)、caffeic acid (2)、rosmarinic acid (3)、methyl rosmarinate (4)、kaempferol 3-O-(4-O-acetyl-alpha-L-rhamnopyranoside) (5)、oresbiusin A (6)、danshensu (7)、methyl melitrate A (8)、netpetoidin B (11)、melitric acid A (12)、sagecoumarin (13)、netpetoidin A (14)、apigenin-6,8-di-C-glucoside (15)、adenosine (16)和rutin (17)。最後，經由黃嘌呤氧化酶抑制活性測試，發現netpetoidin B (11)具有最佳抑制活性，與本實驗室過去結果一致(IC50 11.7 ± 2.5 uM vs. allopurinol 5.3 ± 0.6 uM)。 第二部分 花生衣原花青素之成分研究 糖尿病是一種代謝性疾病，其中，又以第二型糖尿病為主，佔患者總數的90%，主要致病原因可能為胰島素感受性下降。在臨床治療上，常使用以metformin為基礎的處方，再依照病情加入其他用藥，甲型葡萄糖抑制劑便是其中一項。根據電腦分子模擬發現，部分A-type dimeric proanthocyanidins對甲型葡萄糖水解酶具有良好的結合能力，而該化合物曾被報導富含於花生衣中。因此，本研究計畫以花生衣(Arachis hypogaea L.)作為A-type proanthocyanidins的來源，進行化合物結構與甲型葡萄糖水解酶抑制活性間的探討，並期望藉此賦予低經濟價值的花生衣新的再利用途徑。 花生衣的乙醇萃取物經二氯甲烷、乙酸乙酯、正丁醇和水進行極性切割，共劃分為四個可溶部分。取乙酸乙酯可溶部分經Sephadex LH-20做初步分離，利用proanthocyanidins在anisaldehyde顯色後呈現深紅色的特性，並透過ESI-MS尋找對應的分子量作為進一步分離的依據。過程中使用離心式分配層析(centrifugal partition chromatography, CPC)、逆相層析管柱及半製備HPLC等，共計得到13個化合物，經核磁共振光譜及質譜技術分析確認化合物結構為(+)-catechin (18)、(-)-epicatechin (19)、cinnamtannin D1 (20)、proanthocyanidin A1 (21)、proanthocyanidin A4 (22)、proanthocyanidin A2 (23)、epicatechin-(2beta→O→7,4beta→6)-catechin (24)、procyanidin B3 (25)、procyanidin B4 (26)、epicatechin-(2beta→O→7,4beta→8)-ent-epicatechin (27)、epicatechin-(2beta→O→7,4beta→6)-ent-catechin (28)、proanthocyanidin A6 (29)、epicatechin-(2beta→O→7,4beta→6)-ent-epicatechin (30)。另外，經甲型葡萄糖水解酶抑制活性測試發現，化合物24具有最佳抑制活性(IC50 9.7 ± 0.2 uM vs. acarbose 0.023 uM)。 | zh_TW |
| dc.description.abstract | Part 1. Chemical investigation of Hyptis suaveolens guided by xanthine oxidase inhibitory activity
Gout is a kind of metabolic diseases, caused by accumulation of uric acid crystals in the joints. Xanthine oxidase plays an important role in the production of uric acid. Thus, its inhibitor, allopurinol, is often used clinically for long-term gout therapy. This drug, however, might cause Stevens-Johnson syndrome. Therefore, the search for alternative drugs for treating gout is still in need. Our recent studies indicated that some constituents from Hyptis rhomboides are potent xanthine oxidase inhibitors. Thus the aim of this research was to investigate whether the chemical constituents of the related native species, H. suaveolens, possess similar activity. The ethanol extract of H. suaveolens stem was divided into fractions soluble in CH2Cl2, EtOAc, n-BuOH, and water via liquid-liquid partitioning. Further separation was conducted on the EtOAc and n-BuOH-soluble fractions, which possess better anti-xanthine oxidase activity among four fractions. This effort led to the isolation of 17 compounds by combination of Sephadex LH-20, silica gel and reverse-phase column chromatography, centrifugal partition chromatography, and semi-preparative RP-HPLC. Of these, two are new, i.e., dimethyl melitrate A (9) and 9'-O-methyl melitrate A (10). The 15 known ones were identified as ursolic acid (1), caffeic acid (2), rosmarinic acid (3), methyl rosmarinate (4), kaempferol 3-O-(4-O-acetyl--L-rhamnopyranoside) (5), oresbiusin A (6), danshensu (7), methyl melitrate A (8), netpetoidin B (11), melitric acid A (12), sagecoumarin (13), netpetoidin A (14), apigenin-6,8-di-C-glucoside (15), adenosine (16), rutin (17). Their structures were elucidated by MS data and NMR (1D and 2D) spectroscopic analysis. Through xanthine oxidase bioassay, netpetoidin B (11) with IC50 11.7 ± 2.5 uM was found to possess the best inhibitory activity. Part 2. Chemical investigation of proanthocyanidins from peanut skin Diabetes mellitus (DM) is a kind of metabolic disorder. Type 2 DM, which accounts for 90% DM patients, might cause by the decrease of insulin sentivity. Metformin-based regimen was usually used to treat this disorder and the other drugs, such as -glucosidase inhibitor, were added depending on the personal condition. According to the molecular docking, some A-type proanthocyanidins, which are rich in peanut skin, show good docking score toward alpha-glucosidase. As a result, such type compounds were isolated from peanut skin and assayed against alpha-glucosidase to confirm the result of this virtual screening. The ethanol extract of peanut skin was divided into fractions soluble in CH2Cl2, EtOAc, n-BuOH, and water via liquid-liquid partitioning. The EtOAc-soluble fraction was chromatographed over Sephadex LH-20, centrifugal partition chromatography, reverse-phase columns, and semi-preparative RP-HPLC, guided by ESI-MS and TLC, showing red color for dimeric proanthocyanidins while spraying with anisaldehyde reagent. This effort led to the isolation of 13 compounds. Based on 1H and 13C NMR analyses and MS data, they were identified as (+)-catechin (18), (-)-epicatechin (19)、cinnamtannin D1 (20), proanthocyanidin A1 (21), proanthocyanidin A4 (22), proanthocyanidin A2 (23), epicatechin-(2beta→O→7,4beta→6)-catechin (24), procyanidin B3 (25), procyanidin B4 (26), epicatechin-(2beta→O→7,4beta→8)-ent-epicatechin (27), epicatechin-(2beta→O→7,4beta→6)-ent-catechin (28), proanthocyanidin A6 (29), epicatechin-(2beta→O→7,4beta→6)-ent-epicatechin (30). Of these, epicatechin-(2beta→O→7,4beta→6)-catechin (24) with IC50 9.7 ± 0.2 uM was found to possess the best inhibitory activity against alpha-glucosidase. | en |
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| dc.description.tableofcontents | 第一章 香苦草抑制黃嘌呤氧化酶活性成分之研究 1
1. 緒論及研究目的 1 1.1 研究目的 1 1.2 痛風 2 1.2.1 痛風的定義、成因及症狀 2 1.2.2 痛風的臨床治療 3 1.2.3 黃嘌呤氧化酶抑制劑 3 1.2.3.1 Allopurinol 3 1.2.3.2 Febuxostat 4 1.3 黃嘌呤氧化酶與天然物 5 1.3.1 黃嘌呤氧化酶 5 1.3.2 黃酮類(flavonoid)與黃嘌呤氧化酶 5 1.3.3 苯丙烷類(phenylpropanoid)與黃嘌呤氧化酶 6 1.4 香苦草 7 1.4.1 香苦草之簡介 7 1.4.2 香苦草屬(Hyptis)植物成分之文獻回顧 8 2. 實驗結果與討論 23 2.1 三萜類(triterpenoid)成分 25 2.1.1 Ursolic acid (1)之結構解析 25 2.2 苯丙烷類(phenylpropanoid)成分 27 2.2.1 Danshensu (7)和oresbiusin A (6)之結構解析 27 2.2.2 Caffeic acid (2)之結構解析 29 2.2.3 Netpetoidin A (14)和netpetoidin B (11)之結構解析 30 2.2.4 Rosmarinic acid (3)和methyl rosmarinate (4)之結構解析 32 2.2.5 Methyl melitrate A (8)、melitric acid A (12)、9ꞌ-O-methyl melitrate A (10)及dimethyl melitrate A (9)之結構解析 34 2.2.6 Sagecoumarin (13)之結構解析 39 2.3 黃酮類(flavonoid)成分 41 2.3.1 Kaempferol 3-O-(4-O-acetyl--L-rhamnopyranoside) (5)之結構解析 41 2.3.2 Apigenin-6,8-di-C-glucoside (15) 43 2.3.3 Rutin (17) 45 2.4 核苷類(neucleoside)成分 47 2.4.1 Adenosine (16) 47 2.5 黃嘌呤氧化酶抑制活性測試結果 48 2.6 討論 49 3. 實驗部分 51 3.1 儀器與材料 51 3.1.1 理化性質測定儀器 51 3.1.2 成分分離之儀器與材料 51 3.1.3 試劑與溶媒 52 3.1.4 黃嘌呤氧化酶抑制活性測試之試劑與儀器 52 3.2 植物來源 54 3.3 香苦草莖部成分萃取與純化 54 3.3.1 香苦草之萃取 54 3.3.2 香苦草莖部乙酸乙酯可溶部分之分離 54 3.3.2.1 化合物1之分離 55 3.3.2.2 化合物2、3、4、5之分離 55 3.3.2.3 化合物2、3、4、6、7之分離 55 3.3.2.4 化合物3、8之分離 56 3.3.2.5 化合物4、8、9、10、11之分離 56 3.3.2.6 化合物8、12、13、14之分離 56 3.3.2.7 化合物8之分離 57 3.3.3 香苦草莖部正丁醇可溶部分之分離 59 3.3.3.1 化合物15之分離 59 3.3.3.2 化合物2、16、17之分離 59 3.4 化合物之物理數據 61 3.5 黃嘌呤氧化酶抑制活性測試 65 3.5.1 原理 65 3.5.2 實驗方法 65 3.5.2.1 試劑配製 65 3.5.2.2 實驗步驟 66 3.5.2.3 IC50之計算 67 第二章 花生衣原花青素之成分研究 68 1. 緒論及研究目的 68 1.1 研究目的 68 1.2 糖尿病 69 1.2.1 糖尿病的定義、分類及成因 69 1.2.2 第二型糖尿病及其臨床治療 69 1.2.3 甲型葡萄糖水解酶抑制劑 70 1.3 原花青素 72 1.4 花生衣 73 1.4.1 花生之簡介 73 1.4.2 落花生屬(Arachis)植物成分之文獻回顧 74 2. 實驗結果與討論 85 2.1 原花青素類(Proanthocyanidin)成分 87 2.1.1 (+)-Catechin (18)和(-)-epicatechin (19)之結構解析 87 2.1.2 Procyanidin B3 (25)和procyanidin B4 (26)之結構解析 89 2.1.3 Epicatechin-(2→O→7,4→6)-catechin (24)、epicatechin-(2→O→7,4→6)-ent-catechin (28)、proanthocyanidin A6 (29)、epicatechin-(2→O→7,4→6)-ent-epicatechin (30)、proanthocyanidin A1 (21)、proanthocyanidin A2 (23)、epicatechin-(2→O→7,4→8)-ent-epicatechin (27)和proanthocyanidin A4 (22) 93 2.1.3.1 1H和13C NMR資訊及立體構型 93 2.1.3.2 立體結構 94 2.1.3.3 化合物21-24和27-30結構解析 95 2.1.4 Cinnamtannin D1 (20)之結構解析 106 2.2 甲型葡萄糖水解酶抑制活性測試結果 108 2.3 討論 110 3. 實驗部分 113 3.1 儀器與材料 113 3.1.1 理化性質測定儀器 113 3.1.2 成分分離之儀器與材料 113 3.1.3 試劑與溶媒 114 3.1.4 甲型葡萄糖水解酶抑制活性測試之試劑與儀器 114 3.1.5 電腦軟體 115 3.2 植物來源 116 3.3 花生衣成分萃取與純化 116 3.3.1 花生衣之萃取 116 3.3.2 花生衣乙酸乙酯可溶部分成分之小量分離 116 3.3.2.1 化合物18、19之分離 116 3.3.2.2 化合物20、21、22、23之分離 117 3.3.2.3 化合物21之分離 117 3.3.2.4 化合物24之分離 117 3.3.3 花生衣乙酸乙酯可溶部分之大量成分分離 119 3.3.3.1 化合物25及26之分離 119 3.3.3.2 化合物20、21、23、27之分離 119 3.3.3.3 化合物24、28、29、30之分離 120 3.4 化合物之物理數據 123 3.5 甲型葡萄糖水解酶抑制活性測試 127 3.5.1 原理 127 3.5.2 實驗方法 127 3.5.2.1 試劑配製 127 3.5.2.2 實驗步驟 128 3.5.2.3 IC50計算 129 參考資料 130 附圖 146 | |
| dc.language.iso | zh-TW | |
| dc.title | 香苦草抑制黃嘌呤氧化酶活性成分之研究及花生衣原花青素之成分研究 | zh_TW |
| dc.title | Chemical investigation of Hyptis suaveolens guided by xanthine oxidase inhibitory activity and proanthocyanidins from peanut skin | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 104-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 林雲蓮,張溫良,張嘉銓 | |
| dc.subject.keyword | 香苦草,花生衣,黃嘌呤氧化?,甲型葡萄糖水解?,原花青素, | zh_TW |
| dc.subject.keyword | Hyptis suaveolens,peanut skin,xanthine oxidase,alpha-glucosidase,proanthocyanidins, | en |
| dc.relation.page | 224 | |
| dc.identifier.doi | 10.6342/NTU201600422 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2016-06-20 | |
| dc.contributor.author-college | 醫學院 | zh_TW |
| dc.contributor.author-dept | 藥學研究所 | zh_TW |
| 顯示於系所單位： | 藥學系 | |
文件中的檔案：
| 檔案 | 大小 | 格式 | |
|---|---|---|---|
| ntu-105-1.pdf 目前未授權公開取用 | 11.28 MB | Adobe PDF |
系統中的文件，除了特別指名其著作權條款之外，均受到著作權保護，並且保留所有的權利。