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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 沈雅敬 | |
| dc.contributor.author | I-Wen Lo | en |
| dc.contributor.author | 羅宜雯 | zh_TW |
| dc.date.accessioned | 2021-06-16T04:10:51Z | - |
| dc.date.available | 2019-10-20 | |
| dc.date.copyright | 2014-10-20 | |
| dc.date.issued | 2014 | |
| dc.date.submitted | 2014-08-21 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/55584 | - |
| dc.description.abstract | 由台灣產阿里山五味子(Schisandra arisanensis)果實與中國產中國五味子(Schisandra chinensis)果實，經過萃取、分配層析、管柱層析、高效液相層析等分離流程，前者得到二十九個(1-2、16-29、37)降三 類化合物包括kadsuric acid (58)、nigranoic acid (108)，後者得到十三個(13-15、26-28和30-36)降三T類化合物。化合物1-15為新化合物，其中化合物1-12來自前者，而化合物13-15由後者分離純化得到。
依照化合物結構中碳的連結和重排的情形，可將這些降三T類化合物區分為schisanartane (C1；12-13、22-30)、18-norschiartane (C3；14、31-34)、18(13-->14)-abeo-schiartane (C4；35、36)、pre-schisanartane (C5；1-4、16-19)、wuweiziartane (C6；5、20)、arisanartane (C10；15、37)、schicagenin (C12；6-7、21)、16,17-seco-preschisanartane (C13；8)、schisarisanartane (C14)、schisarinin (C18)等結構類型，其中化合物9和10屬於同一新穎骨架類型schisarisanartane (C14)之立體異構物，將之命名為schisarisanlactones A和B；此外化合物11為一個具有2-oxa-bicyclo[2.2.1]heptane系統的schisarinin (C18)新骨架化合物，依生合成推測其衍生自C14類型骨架並命名為schisarinin A。 這些化合物的結構均依據一維核磁共振光譜(1H, 13C, DEPT-135和DEPT-90)以及二維核磁共振光譜(COSY, HSQC, HMBC和NOESY)資料而建立，並輔以紅外線光譜、紫外線光譜、圓二色光譜(CD)、旋光值和高解析電灑式質譜等數據。本文亦推導其可能的生合成路徑，並進行試管內之抗HIV-1 proteinase活性測試。 | zh_TW |
| dc.description.abstract | In our investigations of schinortriterpenoids, 29 compounds (1-12, 16-29, 37, 58 and 108) containing 12 new ones (1-12) were isolated from the fruits of Schisandria arisanensis and 13 compounds (13-15, 26-28 and 30-36) containing 3 new ones (13-15) were obtained from the fruits of S. chinensis. They were separated and purified by means of extraction, partition, and extensive column chromatography including HPLC.
These nortriterpenoids were further classified into ten skeletons according to the different carbon connections and rearrangement patterns as the schisanartane (C1; 12-13, 22-30), 18-norschiartane (C3; 14, 31-34), 18(13-->14)-abeo-schiartane (C4; 35, 36), pre-schisanartane (C5; 1-4, 16-19), wuweiziartane (C6; 5, 20), arisanartane (C10; 15, 37), schicagenin (C12; 6-7, 21), 16,17-seco-preschisanartane (C13; 8), C14 and C18. Schisarisanlactones A (9) and B (10) are a pair of epimer belonging to a novel skeleton-type of schisarisanartane (C14). It is noteful that compound 11 is an unprecedented nortriterpenoid designated schisarinin A, which possesses a novel framework with 2-oxa-bicyclo[2.2.1]heptane system (C18). All the structures were determined by application of 1D NMR (1H, 13C, DEPT-135 and DEPT-90) and 2D NMR (COSY, HSQC, HMBC and NOESY) spectroscopic analysis, plus the interpretation of IR, UV, CD, optical rotation, and HRESIMS. The plausible biosynthetic pathways for these derivatives were also proposed. The isolated compounds were tested in vitro the inhibition of HIV-1 protease activities. As a result, some compounds exhibited moderate anti-HIV-1 protease activities at the concentration of 10 microM with different cell survival rate. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-16T04:10:51Z (GMT). No. of bitstreams: 1 ntu-103-D96423006-1.pdf: 13754420 bytes, checksum: 5a23bdae5934990c407a59646d3ad98a (MD5) Previous issue date: 2014 | en |
| dc.description.tableofcontents | 口試委員會審定書……………………………………………………………… i
誌謝……………………………………………………………ii 中文摘要…………………………………………………… iii 英文摘要………………………………………………………iv 五味子降三T類化合物…………………………………………v 第一章 序論……………………………………………………1 1.1 五味子的藥用歷史…………………………………………1 1.2 五味子的科學分類…………………………………………2 1.2.1 阿里山五味子……………………………………………3 1.2.2 中國五味子………………………………………………3 1.3 五味子三T類成分之文獻回顧…………………………… 4 1.4 人類免疫缺乏症候群(AIDS)與抗HIV藥物……………… 33 1.4.1 人類免疫缺乏病毒(human immunodeficiency virus, HIV)……… 33 1.4.2 抗HIV藥物………………………………………………… 37 1.5 研究動機…………………………………………………… 44 第二章 實驗方法…………………………………………………45 2. 1 材料……………………………………………………… 45 2.1.1 阿里山五味子果實………………………………………45 2.1.2 中國五味子果實……………………………………… 45 2. 2 實驗儀器………………………………………………… 46 2. 3 分離流程…………………………………………………… 48 2.3.1 阿里山五味子未成熟果之分離流程…………………48 2.3.2 阿里山五味子成熟果(2008年)之分離流程…………… 50 2.3.3 阿里山五味子成熟果(2010年)之分離流程…………… 53 2.3.5 中國五味子成熟果之分離流程…………………………… 59 2. 4 試管內之抗HIV-1活性試驗………………………………… 63 2.4.1. Virus and virus infection assay……………………63 2.4.2. Viral load analysis by fast-real time PCR system………63 第三章 實驗結果……………………………………………… 64 3. 1 化合物結構解析………………………………………… 64 3. 1.3 2beta-hydroxylarisanlactone A(5)之結構解析… 76 3. 1.4 Schicagenin D (6)和Iso-schicagenin A (7)之結構解析…………… 81 3. 1.5 化合物8之結構解析………………………………… 88 3. 1.6 Schisarisanlactones A (9)和B (10)之結構解析…… 92 3. 1.7 Schisarinin A (11)之結構解析………………… 98 3. 1.8 Epi-schindilactone H (12)之結構解析………… 103 3. 1.9 Iso-lancifodilactone I (13)之結構解析……… 109 3. 1.10 化合物14 之結構解析…………………………… 114 3. 1.11 Dehydro-arisandilactone A (15)之結構解析… 119 3. 2 試管內之抗HIV-1活性實驗結果…………………… 124 第四章 討論與結論………………………………………… 125 4. 1 阿里山五味子果實之降三T類化合物……………… 127 4. 3 阿里山五味子果實與中國五味子果實之降T類化合物差異… 128 4. 4 化合物之結構活性關係 (SAR)………………………129 第五章 參考文獻…………………………………………… 135 附錄……………………………………………………………150 | |
| dc.language.iso | zh-TW | |
| dc.subject | 五味子 | zh_TW |
| dc.subject | 降三T | zh_TW |
| dc.subject | 抗愛滋病毒 | zh_TW |
| dc.subject | Schisandra sp. | en |
| dc.subject | nortriterpenoids | en |
| dc.subject | anti-HIV | en |
| dc.title | 阿里山五味子與中國五味子果實之降三T類成分研究 | zh_TW |
| dc.title | The Studies of Nortriterpenoids from The Fruits of Schisandra arisanensis and Schisandra chinensis | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 102-2 | |
| dc.description.degree | 博士 | |
| dc.contributor.oralexamcommittee | ?永昌,郭悅雄,李水盛,郭曜豪 | |
| dc.subject.keyword | 五味子,降三T,抗愛滋病毒, | zh_TW |
| dc.subject.keyword | Schisandra sp.,nortriterpenoids,anti-HIV, | en |
| dc.relation.page | 152 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2014-08-21 | |
| 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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