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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 張嘉銓 | zh_TW |
| dc.contributor.advisor | Chia-Chuan Chang | en |
| dc.contributor.author | 黃婉婷 | zh_TW |
| dc.contributor.author | Wan-Ting Huang | en |
| dc.date.accessioned | 2021-07-11T15:31:23Z | - |
| dc.date.available | 2024-02-28 | - |
| dc.date.copyright | 2018-10-09 | - |
| dc.date.issued | 2018 | - |
| dc.date.submitted | 2002-01-01 | - |
| dc.identifier.citation | 1. Hendra, R.; Keller, P. A. Phytochemical studies on two Australian Anigozanthos Plant Species. J. Nat. Prod. 2017, 80, 2141–2145.
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/78947 | - |
| dc.description.abstract | 第一部分：石蓮花化學成分之研究
石蓮花 (Graptopetalum paraguayense) 在台灣民間常作為保肝降壓的養生飲品，相關文獻記載了許多石蓮花萃取物之功效，如抗氧化、抗發炎、降血糖、抗肝纖維化等生物活性。然而有關於石蓮花化學成分的探討，國內已有學者進行主要成分之研究，但其微量化學成分尚未詳細性地研究，因此，本研究利用數種層析方法搭配高效液相層析-固相萃取-管轉移-核磁共振光譜技術(HPLC-SPE-TT-NMR)以針對其中所含可偵測之小分子化學成分進行全面性地分析。 本研究取石蓮花葉部水萃物之甲醇可溶部分，透過Sephadex LH-20、半製備HPLC等管柱進行分離，以及搭配HPLC-SPE-TT-NMR的技術，共分離及鑑定出15個化合物，包含13個黃酮類，1個苯丙烷類以及1個苯甲酸衍生物，其中isorhamnetin 3-O-β-D-glucopyranosyl-6"-O-(3-hydroxy-3-methylglutaryl)-7-O-β-D-glucopyranoside (11), tamarixetin 3-O-β-D-glucopyranosyl-6"-O-(3-hydroxy-3-methylglutaryl)-7-O-β-D-glucopyranoside (12), quercetin 3-O-β-D-glucopyranosyl-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaryl)]-7-O-β-D-glucopyranoside (13), kaempferol 3-O-β-D-glucopyranosyl-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaryl)]-7-O-β-D-glucopyranoside (14) 是新化合物，tamarixetin 3-O-β-D-glucopyranoside (4)、kaempferol 3-O-(2'-O-acetyl)-β-D-glucopyranoside (7)、4-O-β-D-glucopyranosyl-cis-p-coumaric acid (9)、kaempferol 3-O-β-D-glucopyranosyl-6"-O-(3-hydroxy-3-methyl glutaryl)-7-O-β-D-glucopyranoside (10) 為第一次從石蓮花分離得到；此外，透過高效液相層析串聯固相萃取技術分析得到9—13，利用此項串聯技術能節省大量的樣品、時間以及溶劑方面的消耗，仍可得到完整的結構解析資訊，進而對石蓮花的化學成分做一個全面性的探討，並且提供開發為保健食品潛力的資訊。 第二部分：台灣苧麻化學成分之研究 台灣苧麻 (Boehmeria formosana) 為台灣特有種植物，同屬 (Boehmeria) 之植物具有降血糖、抗B型肝炎等生物活性，文獻指出其相關活性成分與原花青素相關。基於上述原因，本研究探討台灣苧麻相關生物活性成分，並以甲型葡萄糖水解酶抑制活性試驗為導向做進一步分離及分析。 將台灣苧麻的乙醇萃取物以液相液相分配方式進行極性劃分，為二氯甲烷、乙酸乙酯、正丁醇、水可溶部分及水不溶物部分。在甲型葡萄糖水解酶抑制活性試驗中，在最終濃度為100 μg/mL，正丁醇層、水層以及乙酸乙酯層皆有95%以上的抑制活性。 台灣苧麻之乙酸乙酯可溶部分利用Sephadex LH-20、CPC、半製備HPLC等層析方法分離，並搭配HPLC-SPE-TT-NMR的技術，共分離及鑑定出13個化合物：trans-ferulic acid (16)、 p-coumaric acid (17)、4-hydroxy benzoic acid (18)、2-O-trans-feruloyl malic acid (19)、3,4-dihydroxybenzoic acid (20)、trans-coumaroyl malic acid (21)、eriodictyol (22)、1,2,4-trihydroxybenzene (23)、dihydroquercetin (24), (+)-catechin (25), (˗)-epicatechin (26)、7"-Oxo-7"-dehydroxycarolignan E (27)以及 boehmenan (28)，其中化合物 (27) 為四聚體苯丙烷類，透過一維、二維核磁共振光譜儀及質譜儀解析，確認為新化合物。 雖然分離乙酸乙酯可溶部分僅得到原花青素的單體(25和26)，推測多聚體在更高極性層，因此，透過LC/MS分析正丁醇可溶部分確實存在有原花青素雙聚體、三聚體或是異構物訊號，而在甲型葡萄糖水解酶抑制活性試驗中，正丁醇可溶部分抑制活性最好，因此，此部分可作為未來研究的方向。 | zh_TW |
| dc.description.abstract | Part 1. Chemical investigation on Graptopetalum paraguayense
Graptopetalum paraguayense is widely used as a healthy drink, which has heptoprotective and hypotensive effects in folk medicine. The related literatures have reported that the G. paraguayense extract has several bioactivities, such as anti-oxidation, anti-inflammation, hypoglycemic effect, anti-fibrosis etc. Although some of the major compounds in G. paraguayense had been identified previously, the minor ones have not been investigated in detail. Therefore, several chromatographic methods and HPLC-SPE-TT-NMR were applied in this study to investigate the chemical components of G. paraguayense comprehensively. In the present reseach, the methanol-soluble fraction of its water extract of G. paraguayense was chromatographed over Sephadex LH-20, semi-preparative RP-HPLC, and HPLC-SPE-TT-NMR, leading to the isolation of 15 compounds, including thirteen flavonoids, one phenylpropanoid and a benzoic acid derivative. Of these, isorhamnetin 3-O-β-D-glucopyranosyl-6"-O-(3-hydroxy-3-methylglutaryl)-7-O-β-D-glucopyranoside (11), tamarixetin 3-O-β-D-glucopyranosyl-6"-O-(3-hydroxy-3-methylglutaryl)-7-O-β-D-glucopyranoside (12), quercetin 3-O-β-D-glucopyranosyl-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaryl)]-7-O-β-D-glucopyranoside (13) and kaempferol 3-O-β-D-glucopyranosyl-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaryl)]-7-O-β-D-glucopyranoside (14) are new and another four compounds which are tamarixetin 3-O-β-D-glucopyranoside (4), kaempferol 3-O-(2'-O-acetyl)-β-D-glucopyranoside (7), 4-O-β-D-glucopyranosyl-cis-p-coumaric acid (9) and kaempferol 3-O-β-D-glucopyranosyl-6"-O-(3-hydroxy-3-methyl glutaryl)-7-O-β-D-glucopyranoside (10) were identified for the first time from G. paraguayense. Besides, 9—13 were obtained by the assistance of the HPLC-SPE-TT-NMR technique. This hyphenation could save amounts of sample, time, and solvent to acquire enough information for elucidation. The comprehensive investigation of G. paraguayense will provide more information for their functional ingredient potentials. Part 2: Chemical investigation on Boehmeria formosana Boehmeria formosana is a plant endogenous to Taiwan. Its related species have been reported to possess bioactivies of anti-glycemic effect and inhibition of HBV production, which is related to proanthocyanidins. The aim of the present study was to investigate whether B. formosana contains the constituents with the mentioned effects, which was accomplished by column chromatography and guided by -glucosidase bioassay. The ethanol extract of B. formosana was divided into CH2Cl2-, EtOAc-, n-BuOH-, water- soluble fractions and the residue via liquid-liquid partitioning procedure. In -glucosidase assay, the EtOAc-, n-BuOH-, and water- soluble fraction showed more than 95% inhibitory activities at a concentration of 100 μg/mL. The EtOAc-soluble fraction was separeated by Sephadex LH-20, centrifugal partition chromatography, and semi-preparative RP-HPLC to give 13 compounds, including trans-ferulic acid (16), p-coumaric acid (17), 4-hydroxy benzoic acid (18), 2-O-trans-feruloyl malic acid (19), 3,4-dihydroxybenzoic acid (20), trans-coumaroyl malic acid (21), eriodictyol (22), 1,2,4-trihydroxybenzene (23), dihydroquercetin (24), (+)-catechin (25), (‐)-epicatechin (26), 7"-oxo-7"-dehydroxycarolignan E (27) and boehmenan (28). Among the isolates, 27 is a novel tetrameric phenylpropanoid based on its 1D-, 2D-NMR and MS spectroscopic data. Although the only the monomers of proanthocyanidins were isolated (i.e. 25 and 26), the possibility of polymeric compounds containing in other hydrophilic fractions. Therefore, small-scale of the n-BuOH-soluble layer was analyzed by LC/MS, and the result demonstrated dimeric, trimeric compounds and their isomers. Besides, n-BuOH-soluble fraction with the best inhibitory activity in -glucosidase assay might be the research interests in the future. | en |
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| dc.description.tableofcontents | 總目錄
口試委員審定書 I 誌謝 II 中文摘要III Abstract V 總目錄 VII 目錄 VII 表目錄 XII 圖目錄 XIV 辭彙 (Glossary) XVII 目錄 第一章 石蓮花化學成分之研究 1 1.研究目的 1 1.1石蓮花 2 1.1.1石蓮花之簡介 2 1.1.2石蓮花生物活性之探討 3 1.1.3風車草屬(Graptopetalum)植物成分之文獻回顧 5 1.2 高效液相層析串聯固相萃取技術 9 2.實驗結果與討論 11 2.1黃酮類(Flavonoids)成分 13 2.1.1 Isoquercitrin (1) 之結構解析 13 2.1.2 Quercetin3-O-6"-(3-hydroxyl-3-methylglutaryl)-β-D-glucopyranoside (2)之結構解析 15 2.1.3 Kaempferol 3-O-β-D-glucopyranoside (3)及Kaempferol 3-O-(2"- acetyl)-β-D-glucopyranoside (7) 之結構解析 17 2.1.4 Tamarixetin 3-O-β-D-glucopyranoside (4) 之結構解析 19 2.1.5 Kaempferol 3-O-[6"-O-(3-hydroxy-3-methylglutaryl)]-β-D-glucopyranoside (5)及kaempferol 3-O-β-D-glucopyranosyl-[6"-O-(3-hydroxy-3-methylglutaryl)]-7-O-β-D-glucopyranoside (10) 之結構解析 21 2.1.6 Quercetin 3-O-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaroyl)]-β-D-glucopyranoside (6)及quercetin 3-O-β-D-glucopyranosyl-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaroyl)]-7-O-β-D-glucopyranoside (13) 之結構解析 26 2.1.7 Kaempferol 3-O-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaryl)]-β-D-glucopyranoside (8)及 kaempferol 3-O-β-D-glucopyranosyl-[2"-O-acetyl-6"-O-(3-hydroxyl-3-methylglutaroyl)]-7-O-β-D-glucopyranoside (14) 之結構解析 30 2.1.8 Isorhamnetin 3-O-β-D-glucopyranosyl-[6"-O-(3-hydroxy-3-methylglutaryl)]-7-O-β-D-glucopyranoside (11)及Tamarixetin 3-O-β-D-glucopyranosyl-[6"-O-(3-hydroxy-3-methylglutaryl)]-7-O-β-D-glucopyranoside (12) 之結構解析 34 2.2 苯丙烷類 37 2.2.1 4-O-β-D-Glucopyranosyl-cis-p-coumaric acid (9) 之結構解析 37 2.3 苯甲酸衍生物 39 2.3.1 4-O-β-D-glucopyranosyl syringic acid (15) 之結構解析 39 2.4 討論 41 3.實驗部分 43 3.1 儀器與材料 43 3.1.1理化性質測定儀器 43 3.1.2成分分離之儀器與材料 43 3.1.3試劑與溶媒 45 3.1.4 薄層層析展開系統 45 3.2 植物來源 46 3.3 石蓮花葉部之成分萃取與純化 46 3.3.1 石蓮花葉部之萃取 46 3.3.2 石蓮花葉部甲醇沖提液部分之分離 46 3.3.2.1 Fr. 4之分離 47 3.3.2.1.1 化合物1、2與3之分離 47 3.3.2.1.2 化合物3、4與5之分離 47 3.3.2.1.3 化合物6、7與8之分離 47 3.3.2.2 Fr. 2之分離 48 3.3.2.2.1 化合物9、10、11、12之分析 48 3.3.2.2.2 化合物13之分析 50 3.3.2.2.3化合物14之分離 52 3.3.2.2.4 化合物15之分離 52 3.4 化合物之物理數據 54 第二章 台灣苧麻化學成分之研究 58 1.研究目的及植物介紹 58 1.1研究目的 58 1.2台灣苧麻 59 1.2.1台灣苧麻之簡介 59 1.2.2苧麻屬(Boehmeria)植物成分之文獻回顧 60 2.實驗結果與討論 66 2.1 甲型葡萄糖水解酶抑制活性之結果 67 2.2苯甲酸衍生物 (Benzoic acid derivatives) 68 2.2.1 4-Hydroxybenzoic acid (18) 與3,4-dihydroxybenzoic acid (20) 之結構解析 68 2.3 苯丙烷類 (Phenylpropanoids) 70 2.3.1 trans-ferulic acid (16) 與p-coumaric acid (17) 之結構解析 70 2.3.2 2-O-trans-Feruloryl malic acid (19)與2-O-trans-p-coumaroyl malic acid (21) 之結構解析 72 2.3.3 化合物7"-Oxo-7"-dehydroxycarolignan E (27) 之結構解析 76 2.4 木脂素 (Lignan) 82 2.4.1 Boehmenan (28)之結構解析 82 2.5 黃酮類 (Flavonoids)成分 86 2.5.1 Eriodictyol (22)之結構解析 86 2.5.2 (2R, 3R)-Dihydroquercetin (24)之結構解析 88 2.5.3 (+)-Catechin (25)和(-)-epicatechin (26)之結構解析 90 2.6 討論 92 3. 實驗部分 93 3.1儀器與材料 93 3.1.1 理化性質測定儀器 93 3.1.2成分分離之儀器與材料 93 3.1.3試劑與溶媒 95 3.2植物來源 96 3.3台灣苧麻根部之成分萃取與純化 96 3.3.1台灣苧麻根部之萃取 96 3.3.1.1 乙酸乙酯層可溶部分之分離 97 3.3.1.1.1 化合物16、17之分離 97 3.3.1.1.2 化合物20、21之分離 97 3.3.1.1.3 化合物18、19之分析 98 3.3.1.1.4 化合物22之分離 100 3.3.1.1.5 化合物23、24之分離 100 3.3.1.2 Fr. 9之分析 100 3.3.1.2.1 化合物25及26之分析 100 3.3.1.2.2 化合物27分析 102 3.3.1.2.3 化合物28分析 104 3.3.1.3 正丁醇可溶部分之小量分析 106 3.3.1.3.1 LC/MS分析Frs. 11~16 106 3.4 化合物之物理數據 110 3.5 甲型葡萄糖水解酶活性試驗 113 3.5.1 實驗原理 113 3.5.2 實驗方法 113 3.5.2.1 相關溶劑及樣品之配製 113 3.5.2.2 實驗步驟 114 | - |
| dc.language.iso | zh_TW | - |
| dc.title | 石蓮花及台灣苧麻化學成分之研究 | zh_TW |
| dc.title | Chemical investigations on Graptopetalum paraguayense and Boehmeria formosana | en |
| dc.type | Thesis | - |
| dc.date.schoolyear | 106-2 | - |
| dc.description.degree | 碩士 | - |
| dc.contributor.oralexamcommittee | 李水盛;李宗徽;林雲蓮 | zh_TW |
| dc.contributor.oralexamcommittee | Shoei-Sheng Lee;Tzong-Huei Lee;Yun-Lian Lin | en |
| dc.subject.keyword | 石蓮花,台灣苧麻,甲型葡萄糖水解?, | zh_TW |
| dc.subject.keyword | Graptopetalum paraguayense,Boehmeria formosana,alpha-glucosidase, | en |
| dc.relation.page | 177 | - |
| dc.identifier.doi | 10.6342/NTU201803562 | - |
| dc.rights.note | 未授權 | - |
| dc.date.accepted | 2018-08-16 | - |
| dc.contributor.author-college | 醫學院 | - |
| dc.contributor.author-dept | 藥學研究所 | - |
| dc.date.embargo-lift | 2023-10-09 | - |
| 顯示於系所單位： | 藥學系 | |
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