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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 沈雅敬 | |
| dc.contributor.author | Hsin-Chan Huang | en |
| dc.contributor.author | 黃馨嬋 | zh_TW |
| dc.date.accessioned | 2021-06-15T04:52:20Z | - |
| dc.date.available | 2011-09-13 | |
| dc.date.copyright | 2010-09-13 | |
| dc.date.issued | 2010 | |
| dc.date.submitted | 2010-07-30 | |
| dc.identifier.citation | 1. http://www.shen-nong.com/chi/herbal/wuweizi.html
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/46048 | - |
| dc.description.abstract | 本論文研究華中五味子(Schisandra sphenanthera Rehd. et Wils)之種子化學成分，從酒精萃取物中分離鑑定出七個新的木質酚素(1-7)和十一個已知化合物(8-18)。新發現的化合物schisphenin B (1)屬於 6,7-seco lignan、schisphentetralone A (2) 屬於aryltetralone-type lignan、schisphenins C-G (3-7)為 C18-dibenzocyclooctadiene lignans 。另外十一個已知化合物中有九個為木質酚素化合物，分別是 pre-gomisin (8)、meso-dihydroguaiaretic acid (9)、veraguensin (10)、(－)-8-epi-aristoligone (11)、benzoylgomisin P (12)、benzoylgomisin U (13)、gomisin F (14)、(+)-gomisin K3 (15)、schisantherin D (16) ，及兩個三萜類化合物 kadsuric acid (17) 和 coccinic acid (18)。
以上化合物的結構是利用核磁共振圖譜1D-NMR (1H-NMR、13C-NMR), 及 2D-NMR (COSY、HMQC、HMBC、NOESY) 及各種物理數據分析，包括旋光度、紅外線、紫外線、CD光譜及高解析電灑式質譜儀，並參考相關文獻而確認。立體結構方面，化合物3-7 的biphenyl moiety部分為S-configuration且cyclooctadiene ring部分均為twist-boat-chair (TBC)構型。 最後將所分得的十八個化合物進行生物活性檢測，利用reporter gene assay測試抗肝纖維化活性，發現化合物1、2、4、11、13、14、18對大鼠肝纖維化細胞有抑制作用，其中以化合物11效果最強。另外抗氧化試驗中發現化合物9有不錯自由基捕捉能力，但仍較vitamin C差。 | zh_TW |
| dc.description.abstract | This research investigated the chemical constituents of the seeds from the medicinal plant Schisandra sphenanthera. From the ethanol extract, seven new oxygenated lignans (1-7), and eleven known compounds (8-18) were isolated. New components could be classified into 6,7-seco dibenzocyclooctadiene type lignan, schisphenin B (1), aryltetralone type lignan, schisphentetralone A (2), and C18-dibenzocyclooctadiene lignans, schisphenins C-G (3-7). The known compounds were identified as nine lignans： pre-gomisin (8), meso-dihydroguaiaretic acid (9), veraguensin (10), (－)-8epi-aristoligone (11), benzoylgomisin P (12), benzoylgomisin U (13), gomisin F (14), (＋)-gomisin K3 (15), and schisantherin D (16), together with two triterpenoids, kadsuric acid (17) and coccinic acid (18).
The structural elucidations of these compounds were determined on the basis of spectroscopic analyses of 1D-NMR (1H and 13C-NMR), 2D-NMR (COSY, HMQC, HMBC, NOESY) techniques, physical methods including optical rotation, IR, UV, CD, HRESIMS, as well as by comparison of the published data. The CD results showed that the biphenyl groups of new compounds 3-7 were all S-configuration and the analyses of NOESY correlations revealed that the octadiene moieties of them were twist-boat-chair conformation. Biological activities of all isolated components were evaluated as well. The reporter gene assay was used to measure anti-liver fibrosis effect in this study. Compounds 1, 2, 4, 11, 13, 14, 18 were regarded as better anti-inflammatory activity substances on HSC-T6 test. Among them, 11 is the most potential one because its activity is better than the positive control, silymarin. The DPPH free-radical scavenging experiment indicated that compound 9 exhibited good effect at 0.006 M (scarvenging activity 55.4%), but it was worse than vitamin C at 0.0057 M (scarvenging activity 95.8%). | en |
| dc.description.provenance | Made available in DSpace on 2021-06-15T04:52:20Z (GMT). No. of bitstreams: 1 ntu-99-R97423016-1.pdf: 4709110 bytes, checksum: e81366ee169b9abbe738c6bdb6e88e55 (MD5) Previous issue date: 2010 | en |
| dc.description.tableofcontents | 謝辭 I
第一章 序論 1 第一節 前言 1 第二節 相關化合物之文獻回顧 3 第二章 材料及方法 42 第一節 材料介紹 42 第二節 分離流程 43 第三節 實驗儀器 51 第四節 實驗溶劑及矽膠 52 第五節 化合物結構測定之方法 53 第三章 實驗結果 54 第一節 化合物1之結構解析 54 第二節 化合物2之結構解析 63 第三節 化合物3之結構解析 73 第四節 化合物4之結構解析 84 第五節 化合物5之結構解析 93 第六節 化合物6之結構解析 103 第七節 化合物7之結構解析 112 第八節 化合物8之結構 121 第九節 化合物9之結構 122 第十節 化合物10之結構 123 第十一節 化合物11之結構 124 第十二節 化合物12之結構 125 第十三節 化合物13之結構 126 第十四節 化合物14之結構 127 第十五節 化合物15之結構 128 第十六節 化合物16之結構 129 第十七節 化合物17之結構解析 130 第十八節 化合物18之結構解析 131 第十九節 抗肝炎細胞活性測試 (一)： 132 第二十節 DPPH free-radical scarvenging test (二)： 135 第二十一節 生物活性與結構之關係(SAR) 136 第四章 結論 137 參考文獻 141 圖目錄 Schisphenin B (1) 圖1- 1、Schisphenin B (1) 之COSY及HMBC correlations 55 圖1- 2、Schisphenin B (1) 之NOESY correlations 56 圖1- 3、Schisphenin B (1) 之UV光譜 58 圖1- 4、Schisphenin B (1) 之IR光譜 58 圖1- 5、Schisphenin B (1) 之CD光譜 59 圖1- 6、Schisphenin B (1) 之HRESIMS光譜 59 圖1- 7、Schisphenin B (1) 之1H-NMR圖譜 (400 MHz) 60 圖1- 8、Schisphenin B (1) 之13C-NMR圖譜 (100 MHz) 60 圖1- 9、Schisphenin B (1) 之COSY圖譜 (400 MHz) 61 圖1- 10、Schisphenin B (1) 之HMQC圖譜 (400 MHz) 61 圖1- 11、Schisphenin B (1) 之HMBC圖譜 (400 MHz) 62 圖1- 12、Schisphenin B (1) 之NOESY圖譜 (400 MHz) 62 圖1- 13、Schisphenin B (1) 之1H-NMR圖譜 (400 MHz) 60 圖1- 14、Schisphenin B (1) 之13C-NMR圖譜 (100 MHz) 60 圖1- 15、Schisphenin B (1) 之COSY圖譜 (400 MHz) 61 圖1- 16、Schisphenin B (1) 之HMQC圖譜 (400 MHz) 61 圖1- 17、Schisphenin B (1) 之HMBC圖譜 (400 MHz) 62 圖1- 18、Schisphenin B (1) 之NOESY圖譜 (400 MHz) 62 Schisphentetralone A (2) 圖2-1、Schisphentetralone A (2) 之COSY及 HMBC correlations 64 圖2- 2、Schisphentetralone A (2) 之NOESY correlations 66 圖2- 3、Schisphentetralone A (2) 之UV光譜 68 圖2- 4、Schisphentetralone A (2) 之IR光譜 68 圖2- 5、Schisphentetralone A (2) 之CD光譜 69 圖2- 6、Schisphentetralone A (2) 之HRESIMS圖譜 69 圖2- 7、Schisphentetralone A (2) 之1H-NMR圖譜 (400 MHz) 70 圖2- 8、Schisphentetralone A (2) 之13C-NMR圖譜 (100 MHz) 70 圖2- 9、Schisphentetralone A (2) 之COSY圖譜 (400 MHz) 71 圖2- 10、Schisphentetralone A (2) 之HMQC圖譜 (400 MHz) 71 圖2- 11、Schisphentetralone A (2) 之HMBC圖譜 (400 MHz) 72 圖2- 12、Schisphentetralone A (2) 之NOESY圖譜 (400 MHz) 72 Schisphenin C (3) 圖3- 1、Schisphenin C (3) 之COSY及HMBC correlations 74 圖3- 2、Schisphenin C (3) 之 NOESY correlations 76 圖3- 3、Schisphenin C (3) 之UV光譜 79 圖3- 4、Schisphenin C (3) 之IR光譜 79 圖3- 5、Schisphenin C (3) 之CD光譜 80 圖3- 6、Schisphenin C (3) 之HRESIMS 圖譜 80 圖3- 7、Schisphenin C (3) 之1H-NMR圖譜 (400 MHz) 81 圖3- 8、Schisphenin C (3) 之13C-NMR圖譜 (100 MHz) 81 圖3- 9、Schisphenin C (3) 之COSY圖譜 (400 MHz) 82 圖3- 10、Schisphenin C (3) 之HMQC圖譜 (400 MHz) 82 圖3- 11、Schisphenin C (3) 之HMBC圖譜 (400 MHz) 83 圖3- 12、Schisphenin C (3) 之NOESY圖譜 (400 MHz) 83 Schisphenin D (4) 圖4- 1、Schisphenin D (4) 之COSY及HMBC correlations 85 圖4- 2、Schisphenin D (4) 之 NOESY correlations 86 圖4- 3、Schisphenin D (4) 之UV光譜 88 圖4- 4、Schisphenin D (4) 之IR光譜 88 圖4- 5、Schisphenin D (4) 之CD光譜 89 圖4- 6、Schisphenin D (4)之HRESIMS圖譜 89 圖4- 7、Schisphenin D (4) 之1H-NMR圖譜 (200 MHz) 90 圖4- 8、Schisphenin D (4) 之13C-NMR圖譜 (50 MHz) 90 圖4- 9、Schisphenin D (4) 之COSY圖譜 (400 MHz) 91 圖4- 10、Schisphenin D (4) 之HMQC圖譜 (400 MHz) 91 圖4- 11、Schisphenin D (4) 之HMBC圖譜 (400 MHz) 92 圖4- 12、Schisphenin D (4) 之NOESY圖譜 (400 MHz) 92 Schisphenin E (5) 圖5- 1、Schisphenin E (5) 之COSY及 HMBC correlations 94 圖5- 2、Schisphenin E (5) 之 NOESY correlations 95 圖5- 3、Schisphenin E (5) 之UV光譜 98 圖5- 4、Schisphenin E (5) 之IR光譜 98 圖5- 5、Schisphenin E (5) 之CD光譜 99 圖5- 6、Schisphenin E (5) 之HRESIMS圖譜 99 圖5- 7、Schisphenin E (5) 之1H-NMR圖譜 (200 MHz) 100 圖5- 8、Schisphenin E (5) 之13C-NMR圖譜 (50 MHz) 100 圖5- 9、Schisphenin E (5) 之COSY圖譜 (400 MHz) 101 圖5- 10、Schisphenin E (5) 之HMQC圖譜 (400 MHz) 101 圖5- 11、Schisphenin E (5) 之HMBC圖譜 (400 MHz) 102 圖5- 12、Schisphenin E (5) 之NOESY圖譜 (400 MHz) 102 Schisphenin F (6) 圖6- 1、Schisphenin F (6) 之COSY及HMBC correlations 104 圖6- 2、Schisphenin F (6) 之NOESY correlations 105 圖6- 3、Schisphenin F (6) 之UV光譜 107 圖6- 4、Schisphenin F (6) 之IR光譜 107 圖6- 5、Schisphenin F (6) 之CD光譜 108 圖6- 6、schisphenin F (6) 之HRESIMS圖譜 108 圖6- 7、Schisphenin F (6) 之1H-NMR圖譜 (400 MHz) 109 圖6- 8、Schisphenin F (6) 之13C-NMR圖譜 (100 MHz) 109 圖6- 9、Schisphenin F (6) 之COSY圖譜 (400 MHz) 110 圖6- 10、Schisphenin F (6) 之HMQC圖譜 (400 MHz) 110 圖6- 11、Schisphenin F (6) 之HMBC圖譜 (400 MHz) 111 圖6- 12、Schisphenin F (6) 之NOESY圖譜 (400 MHz) 111 Schisphenin G (7) 圖7- 1、Schisphenin G (7) 之COSY及HMBC correlations 113 圖7- 2、Schisphenin G (7) 之NOESY correlations 114 圖7- 3、Schisphenin G (7) 之UV光譜 116 圖7- 4、Schisphenin G (7) 之IR光譜 116 圖7- 5、Schisphenin G (7) 之 CD光譜 117 圖7- 6、Schisphenin G (7) 之HRESIMS圖譜 117 圖7- 7、Schisphenin G (7) 之1H-NMR圖譜 (200 MHz) 118 圖7- 8、Schisphenin G (7) 之13C-NMR圖譜 (50 MHz) 118 圖7- 9、Schisphenin G (7) 之COSY圖譜 (400 MHz) 119 圖7- 10、Schisphenin G (7) 之HMQC圖譜 (400 MHz) 119 圖7- 11、Schisphenin G (7) 之HMBC圖譜 (400 MHz) 120 圖7- 12、Schisphenin G (7) 之NOESY圖譜 (400 MHz) 120 圖 一、華中五味子 (Schisandra sphenanthera) 果實分離流程（I） 45 圖 二、華中五味子 (Schisandra sphenanthera) 果實分離流程（II） 46 圖 三、華中五味子 (Schisandra sphenanthera) 果實分離流程（III） 47 圖 四、華中五味子 (Schisandra sphenanthera) 果實分離流程（IV） 48 圖 五、化合物A-C之CD光譜 65 圖 六、Biphenyl moiety之S、R-configurations 75 圖 七、Correlations between TBC and TB conformations 76 圖 八、Interconversion of TBC and TB conformations 77 圖 九、Activity of compounds 1-18 on inflammatory HSC-T6 132 圖 十、Silymarin 對INF-α誘導的HSC-T6細胞的抑制活性 133 圖 十一、Inhibitory ratio of compounds 1-18 on inflammatory HSC-T6 133 圖 十二、Luciferase 氧化發光過程 134 圖 十三、DPPH 補捉自由基或抗氧化物質的反應式 135 圖 十四、Scarvenging activity of lignans and vit. C 135 圖 十五、化合物1生合成路徑推導 138 圖 十六、化合物2生合成路徑推導 139 圖 十七、化合物3-7生合成路徑推導 140 表目錄 表 一、Schisphenin B (1) 物理資料與1H、13C-NMR數據 (CDCl3) 55 表 二、Schisphentetralone A (2) 物理資料與1H、13C-NMR數據 (Acetone-d6) 65 表 三、Schisphenin C (3) 物理資料與1H、13C-NMR數據 (CDCl3) 76 表 四、Schisphenin D (4) 物理資料與1H、13C-NMR數據 (CDCl3) 85 表 五、Schisphenin E (5) 物理資料與1H、13C-NMR數據 (CDCl3) 94 表 六、Schisphenin E (5) 在Pyridine-d5溶劑中的NMR 數據 95 表 七、Arisanschinin G (6) 物理資料與1H、13C-NMR數據 (Acetone-d6) 104 表 八、Schisphenin G (7) 物理資料與1H、13C-NMR數據 (CDCl3) 113 表 九、Pre-gomisin (8) 之1H、13C-NMR數據 (CDCl3) 119 表 十、化合物meo-dihydroguaiaretic acid (9)之1H、13C-NMR數據 (CDCl3) 120 表 十一、Veraguensin (10) 之1H、13C-NMR 數據 (CDCl3) 121 表 十二、(－)-8'-Epi-aristoligone (11) 之1H、13C-NMR數據 (CDCl3) 122 表 十三、Benzoylgomisin P (12) 之1H、13C-NMR數據 (CDCl3) 123 表 十四、Benzoylgomisin U (13) 之1H、13C-NMR數據(CDCl3) 124 表 十五、Gomisin F (14) 之1H、13C-NMR數據 (CDCl3) 125 表 十六、Gomisin K3 (15) 之1H、13C-NMR數據 (CDCl3) 126 表 十七、Schisantherin D (16) 之1H、13C-NMR數據 (CDCl3) 127 表 十八、Kadsuric acid (17) 之1H、13C-NMR數據 (CDCl3) 128 表 十九、Coccinic acid (18) 之1H、13C-NMR數據 (CDCl3) 129 | |
| dc.language.iso | zh-TW | |
| dc.subject | dibenzocyclooctadiene | zh_TW |
| dc.subject | 華中五味子 | zh_TW |
| dc.subject | 種子 | zh_TW |
| dc.subject | 木質酚素 | zh_TW |
| dc.subject | aryltetralone | zh_TW |
| dc.subject | aryltetralone | en |
| dc.subject | Schisandra sphenanthera | en |
| dc.subject | dibenzocyclooctadiene | en |
| dc.subject | seeds | en |
| dc.subject | ignan | en |
| dc.title | 華中五味子種子活性木質酚素成分之研究 | zh_TW |
| dc.title | Bioactive Lignans from the Seeds of Schisandra sphenanthera | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 98-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 李水盛,周宏農 | |
| dc.subject.keyword | 華中五味子,種子,木質酚素,aryltetralone,dibenzocyclooctadiene, | zh_TW |
| dc.subject.keyword | Schisandra sphenanthera,seeds,ignan,aryltetralone,dibenzocyclooctadiene, | en |
| dc.relation.page | 153 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2010-08-02 | |
| 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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