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http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/76818完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 張嘉銓(Chia-Chuan Chang) | |
| dc.contributor.author | Wan-Chia Tsai | en |
| dc.contributor.author | 蔡宛珈 | zh_TW |
| dc.date.accessioned | 2021-07-10T21:37:44Z | - |
| dc.date.available | 2021-07-10T21:37:44Z | - |
| dc.date.copyright | 2020-09-10 | |
| dc.date.issued | 2020 | |
| dc.date.submitted | 2020-08-18 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/76818 | - |
| dc.description.abstract | 第一部分:台灣苧麻莖部化學成分之研究 台灣苧麻 (Boehmeria formosana) 為台灣原生之蕁麻科植物，分布於台灣還有日本及中國大陸。同屬植物具有降血糖、抗B型肝炎，與抗癌等活性。而在本實驗室先前研究中，發現台灣苧麻葉部具有多種菲併吲哚啶(phenanthroindolizidine)與菲併喹啉(phenathroquinolizidine)類生物鹼的成分，文獻中報導具有抗發炎、抗微生物、抗癌、抗痢疾等生物活性。基於上述原因，本研究進而探討此植物之莖部中生物鹼及其他生物活性成分，藉以評估台灣苧麻莖部對於藥用的潛力。 莖部乙醇萃取物以液相-液相分配進行極性分割，得到二氯甲烷、乙酸乙酯、正丁醇層與水四個可溶部分。乙酸乙酯及二氯甲烷可溶部分利用Sephadex LH-20、矽膠正相及逆相和半製備高效能液相層析管柱進行分離，純化並鑑定出10個化合物: para-coumaric acid (1)、5-O-caffeoylshikimic acid (2) taxifolin (3)、eriodictyol (4)、luteolin (5)、quercetin 3-O-α-L-rhamnoside (6)、5,7-dihydroxychromone (7)、ficuseptine (8)、4a,4b-seco-dehydroantofine (9)及(+)-antofine (10)。 上述成分之化學結構主要係藉由一維與二維解析核磁共振譜並搭配質譜資料而得到。文獻報導4a,4b-seco-dehydroantofine (9)及(+)-antofine (10)對於肺癌、肝癌細胞具有抑制作用。 第二部分:塊莖蘆莉草化學成分之研究 塊莖蘆莉草 (Ruellia tuberosa) 原產於中美洲和南美洲熱帶地區，分佈於東南亞印尼、印度、巴基斯坦和臺灣等熱帶地區。此植物為爵床科之蘆利草屬植物，同屬植物具有調控血糖、抗氧化、抗發炎與抗癌等生物活性。因此探討此植物之化學成分，藉以釐清本植物之活性來源成分。 全株乙醇萃取物依序以等體積之正己烷、乙酸乙酯、正丁醇層與水層，以液相-液相分配進行極性分割，共得到四個可溶部分。乙酸乙酯可溶部分利用Sephadex LH-20、矽膠管柱、逆向層析管柱及半製備高效能液相層析管柱進行分離，並純化鑑定出16個化合物: para-hydroxylbenzaldehyde (11)、vanillin (12)、indole-3-carboxaldehyde (13)、cirsimatin (14)、caffeic acid (15)、acteoside (16)、isoacteoside (17)、isonuomioside (18)、fucatoside A (19)、cirsimarin (20)、allantoin (21)、adenine (22)、indole-3-carboxylic acid (23)、tyrosol (24)、stigmasterol (25)、lupeol (26)。 上述成分之結構主要係藉由解析核磁共振譜(氫、碳-13與二維圖譜)並搭配質譜資料而得到。而其中acteoside (16) 具有抗氧化活性，對於血糖與血管收縮素轉換酶(anti-angiotensin-converting enzyme)皆具有抑制效果；isoacteoside (17) 具有抗菌、抗氧化、抗發炎，與肝保護等生物活性。 | zh_TW |
| dc.description.abstract | Part 1: Chemical investigations on the stem of Boehmeria formosana Boehmeria formosana is an indogenous Urticaceae plant of Taiwan, distributed not only in Taiwan, but also in Japan and mainland China. The species from the same genus possess the activities of anti-hyperglycemia, inhibition of HBV production anti-cancer, etc. In the previous studies of our lab, aboundant phenanthroindolizidines and phenathroquinolizidines were isolated from the leaves of B. formosana, and these compounds are reported to demonstrate many biological activities, such as anti-inflammation, anti-microorganism, anti-cancer and anti-dysentery. Thus, the aim of the present study was to investigate the chemical constituents from B. formosana stem and evaluate the potential of B. formosana in medicinal uses. The ethanol extract of the B. formosana stem was divided into four fractions (dichloromethane-, ethyl acetate-, n-butanol-, and water- soluble fractions) by liquid-liquid partition. The ethyl acetate- and dichloromethane- soluble fractions were further separated by Sephadex LH-20, silica gel, RP-18 and semi-preparative RP-18 HPLC chromatography to give 10 compounds, including para-coumaric acid (1), 5-O-caffeoylshikimic acid (2), taxifolin (3), eriodictyol (4), luteolin (5), quercetin 3-O-α-L-rhamnoside (6), 5,7-dihydroxychromone (7), ficuseptine (8), 4a,4b-seco-dehydroantofine (9), and (+)-antofine (10). The structures of the aforementioned compounds were elucidated mainly by spectroscopic analyses of 1D and 2D NMR and assisted by MS data. 4a,4b-seco-dehydroantofine (9) and (+)-antofine (10) were reported to inhibit the growth of lung, liver cancer cells. Part 2: Chemical investigations on whole plant of Ruellia tuberosa Ruellia tuberosa is Acanthaceous herb native to tropical regions of central and south America, and is distributed in Southeast Asia, Indonesia, India, Pakistan and Taiwan. The species of the same genus were reported to possess bioactivities such as anti-glycemia, antioxidation, anti-inflammation, anti-cancer, etc. Therefore, the present study was to investigate the chemical constituents to clarify the resource compounds of its activities. The ethanol extract plant of R. tuberosa was divided into four soluble fractions (n-hexane-, ethyl acetate-, n-butanol-, and water- soluble fractions) by liquid-liquid partition. The ethyl acetate-soluble fraction were further separated by Sephadex LH-20, silica gel, RP-18 and semi-preparative RP-18 HPLC chromatography to give 16 compounds, including para-hydroxylbenzaldehyde (11), vanillin (12), indole-3-carboxaldehyde (13), cirsimatin (14), caffeic acid (15), acteoside (16), isoacteoside (17), isonuomioside (18), fucatoside A (19), cirsimarin (20), allantoin (21), adenine (22), indole-3-carboxylic acid (23), tyrosol (24), stigmasterol (25), and lupeol (26). The structures of the aforementioned compounds were elucidated mainly by 1D and 2D NMR spectroscopic analyses and assisted by MS data. Acteoside (16) was reported to demonstrate antioxidant, anti-angiotensin converting enzyme (ACE) activities and anti-hyperglycemic effect in vitro, isoacteoside (17) exhibited antimicrobial activity against Gram-positive and negative bacteria. | en |
| dc.description.provenance | Made available in DSpace on 2021-07-10T21:37:44Z (GMT). No. of bitstreams: 1 U0001-1608202019202900.pdf: 7372675 bytes, checksum: 98db7beebb96ddb86073b1c93289740b (MD5) Previous issue date: 2020 | en |
| dc.description.tableofcontents | 中文摘要 III Abstract V 總目錄 VII 流程圖目錄(List of Schemes) XII 表目錄(List of Tables) XIII 圖目錄(List of Figures) XV 專有名詞縮寫(Abbreviatoin of Terminology) XX 壹、台灣苧麻化學成分之研究 1 1. 植物簡介及研究目的 1 1.1植物簡介 1 1.1.1苧麻屬(Boehmeria)植物成分之文獻回顧 2 1.2 研究目的 14 2. 實驗結果與討論 15 2.1 苯丙烷類 (Phenylpropanoids) 16 2.1.1 p-Coumaric acid (1) 之結構解析 16 2.1.2 5-O-Caffeoyl shikimic acid (2) 之結構解析 17 2.2 黃酮類 (Flavonoids) 19 2.2.1 Taxifolin (3) 之結構解析 19 2.2.2 Eriodictyol (4) 之結構解析 21 2.2.3 Luteolin (5) 之結構解析 23 2.2.4 Quercetin 3-O-α-L-rhamnoside (6) 之結構解析 25 2.2.5 5,7-Dihydroxychromone (7) 之結構解析 28 2.3 菲併吲哚啶生物鹼衍生物 (Secophenanthroindolizidine alkaloids) 30 2.3.1 Ficuseptine (8) 之結構解析 30 2.3.2 4a,4b-seco-Dehydroantofine (9) 之結構解析 32 2.4 菲併喹啉生物鹼衍生物 (Secophenanthroquinolizidine alkaloids) 34 2.4.1 (+)-Antofine (10) 之結構解析 34 2.5 討論 36 2.5.1 化學成分於台灣苧麻之分布與含量 36 2.5.2 化合物8-10之生合成推測 38 3. 實驗部分 40 3.1儀器與器材 40 3.1.1理化性質測定儀器 40 3.1.2成分分離之儀器與器材 40 3.1.3 試劑與溶劑 41 3.2 植物來源 42 3.3台灣苧麻莖部化學成分之分離 42 3.3.1台灣苧麻莖部之萃取 42 3.3.2乙酸乙酯可溶層之分離 43 3.3.2.1化合物1之分離 43 3.3.2.2化合物2及6之分離 43 3.3.2.3化合物3之分離 44 3.3.2.4 化合物4之分離 44 3.3.2.5化合物5之分離 45 3.3.3二氯甲烷可溶層之分離 45 3.3.3.1化合物7之分離 46 3.3.3.2化合物8~10之分離 46 3.4 化合物之物理數據 49 第二章 塊莖蘆莉草化學成分之研究 52 1. 植物介紹及研究目的 52 1.1 植物介紹 52 1.2 研究目的 53 1.2.1 蘆莉草屬(Ruellia)植物成分之文獻回顧 54 1.3 苯乙醇苷(Phenylethanoid glycosides) 65 1.3.1 簡介 65 1.3.2 苯乙醇苷 (Phenylethanoid glycosides) 生合成途徑 68 1.3.3 苯乙醇苷 (Phenylethanoid glycosides) 結構與生物活性 71 2. 實驗結果與討論 82 2.1 苯乙醇苷類之單醣組成鑑定方法 83 2.1.1 實驗目的 83 2.1.2苯乙醇苷類之酸水解 83 2.1.3苯乙醇苷類酸水解後單醣之標定 84 2.1.3.1 單糖標定之製備方法 85 2.1.4 單糖-PMP之高效能液相層析偵測 86 2.2 苯甲醛類 (Benzaldehydes) 87 2.2.1 p-Hydroxylbenzaldehyde (11) 之結構解析 87 2.2.2 Vanillin (12) 之結構解析 88 2.3 吲哚生物鹼衍生物(Indole alkaloids) 89 2.3.1 Indole-3-carboxaldehyde (13) 之結構解析 89 2.4 黃酮類 (Flavonoids) 91 2.4.1 Cirsimaritin (14) 之結構解析 91 2.5 苯丙烷類 (Phenylpropanids) 93 2.5.1 Caffeic acid (15) 之結構解析 93 2.6 苯乙醇苷類 (Phenylethanoid glycosides) 95 2.6.1 Acteoside (16) 之結構解析 95 2.6.2 Isoacteoside (17) 之結構解析 99 2.6.3 Isonuomioside (18) 之結構解析 102 2.6.4 Fucatoside A (19) 之結構解析 105 3. 化合物結構鑑定 108 3.1黃酮類 (Flavonoids) 108 3.1.1 Cirsimarin (20) 之結構鑑定 108 3.2 乙內醯脲衍生物 (Hydantoin) 110 3.2.1 Allantoin (21) 之結構鑑定 110 3.3 嘌呤類 (Purine) 111 3.3.1 Adenine (22) 之結構鑑定 111 3.4 吲哚生物鹼衍生物(Indole-type alkaloids) 112 3.4.1 Indole-3-carboxylic acid (23) 之結構鑑定 112 3.5 苯丙烷類 (Phenylpropanoids) 113 3.5.1 Tyrosol (24) 之結構鑑定 113 3.6 固醇類 (Steroids) 114 3.6.1 Stigmasterol (25) 之結構鑑定 114 3.7 萜類 (Terpenoids) 116 3.7.1 Lupeol (26) 之結構鑑定 116 4. 討論 118 4.1 苯乙醇苷類化合物一維核磁共振訊號特徵探討 118 4.2 苯乙醇苷類化合物16與抗糖尿病活性之關聯 122 5. 實驗部分 123 5.1儀器與器材 123 5.2植物來源 123 5.3塊莖蘆莉草化學成分之分離 123 5.3.1塊莖蘆莉草之萃取 123 5.3.2 乙酸乙酯可溶部分之分離 124 5.3.2.1 化合物11及12之分離 124 5.3.2.2 化合物13及14之分離 125 5.3.2.3 化合物16及17之分離 126 5.3.2.4 化合物15之分離 128 5.3.2.5 化合物18之分離 129 5.3.2.6 化合物19之分離 130 5.4化合物11~19之物理數據 133 附圖 149 | |
| dc.language.iso | zh-TW | |
| dc.subject | 台灣苧麻 | zh_TW |
| dc.subject | 塊莖蘆莉草 | zh_TW |
| dc.subject | Boehmeria formosana | en |
| dc.subject | Ruellia tuberosa | en |
| dc.title | 台灣苧麻莖部暨塊莖蘆莉草化學成分之研究 | zh_TW |
| dc.title | Chemical investigation on Boehmeria formosana stem and Ruellia tuberosa | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 108-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 李水盛(Shoel-Sheng Lee),林雲蓮(Yun-Lian Lin) | |
| dc.subject.keyword | 台灣苧麻,塊莖蘆莉草, | zh_TW |
| dc.subject.keyword | Boehmeria formosana,Ruellia tuberosa, | en |
| dc.relation.page | 211 | |
| dc.identifier.doi | 10.6342/NTU202003604 | |
| dc.rights.note | 未授權 | |
| dc.date.accepted | 2020-08-18 | |
| 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 | |
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