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http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/55796完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 沈雅敬(Ya-Ching Shen) | |
| dc.contributor.author | Chia-Hsun Fang | en |
| dc.contributor.author | 方嘉勲 | zh_TW |
| dc.date.accessioned | 2021-06-16T05:08:36Z | - |
| dc.date.available | 2019-10-20 | |
| dc.date.copyright | 2014-10-20 | |
| dc.date.issued | 2014 | |
| dc.date.submitted | 2014-08-19 | |
| dc.identifier.citation | 1. Aalbersberg, W.; Singh, Y. Dammarane triterpenoids from Dysoxylum richii. Phytochemistry 1991, 30, 921-926.
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/55796 | - |
| dc.description.abstract | 在活性篩選時發現紅果椌木枝葉之乙醇萃取物具有抗發炎效果，根部之乙醇萃取物則有抗人類癌細胞之效用。因此本論文主要研究其所含有的化學結構和其生物活性，又鑑於蔡耀慶學長已從一部份枝葉之乙醇萃取物中分離出一些有活性之雙萜類化合物，因而將重點著重於有活性之雙萜類尋找。所用之方法即利用各式管柱色層分析方法進行分離並鑑定其所含之化學成分。
實驗結果共分離出10個化合物，共有3個屬於labdane骨架的雙萜類新化合物1-3，4個屬於prenyleudesmane骨架的雙萜類新化合物4-7，以及3個已知化合物 (－)-3β-hydroxy-15,16-dinorlabd-8(17)-ene-13-one (8)、dysokusones A (9)、4,5-epoxy-β-caryophyllene (10)。 以上分離獲得之化合物利用核磁共振圖譜1D NMR (1H-NMR、13C-NMR)及2D NMR (HSQC、HMBC、COSY、NOESY)，並加上各種物理方法; 如比旋光度、紫外線光譜、圓二色性光譜及高解析電灑式質譜，以及利用化學資料庫Reaxys查詢相關文獻以鑑定結構。最後將所獲得之化合物進行抗發炎、抗癌與抗病毒等生物活性檢測。 關鍵字：紅果椌木、雙萜類、倍半萜類、抗發炎與抗癌細胞活性 | zh_TW |
| dc.description.abstract | In preliminary bioactive screening, the ethanolic extract of leaves and twigs from Dysoxylum hongkongense exhibited significant anti-inflammatory activities while the extract of roots exhibited cytotoxicity against human cancer cells. On the other hand, our lab member, Yao-Ching Tsai has previously separated some bioactive diterpenoids from ethanolic extract of leaves and twigs. Thus this thesis mainly focuses on finding more bioactive diterpenoids from the twigs, leaves and roots of Dysoxylum hongkongense. A variety of chromatographic methods were used to fractionate and separate and finally got ten compounds.
Among them, compounds 1-3 are new diterpenes of labdane-type and compounds 4-7 belong to new diterpenes of the prenyleudesmane type. In addition, compounds 8-10 are known compounds, (－)-3β-hydroxy-15,16-dinorlabd-8(17)-ene-13-one, dysokusones A and 4,5-epoxy-β-caryophyllene. The above structures were elucidated on the basis of spectroscopic analysis such as 1D NMR (1H-NMR、13C-NMR), 2D NMR (HSQC、HMBC、COSY、NOESY) techniques and physical methods including optical rotation, ultraviolet spectroscopy (UV), circular dichroism spectroscopy (CD) and high resolution mass spectroscopy (HRMS). Besides, the data of all compounds were compared with the published literatures by searching the chemical database of REAXYS. Finally, these compounds have been tested and evaluated their biological activities including anti-inflammatory, cytotoxic and anti-viral effects. Keywords: Dysoxylum hongkongense、diterpenoids、sesquiterpenoids、labdanes、prenyleudesmanes、anti-inflammatory、cytotoxic activities | en |
| dc.description.provenance | Made available in DSpace on 2021-06-16T05:08:36Z (GMT). No. of bitstreams: 1 ntu-103-R01423022-1.pdf: 8427477 bytes, checksum: 973397461cd0cebd525f3b60c598d7b9 (MD5) Previous issue date: 2014 | en |
| dc.description.tableofcontents | 目錄
謝辭 I 中文摘要 II Abstract III 目錄 V 圖目錄 VII 表目錄 XI 第一章 序論 1 第一節 前言 1 第二節 紅果椌木相關化合物之文獻回顧 3 第二章 材料與方法 28 第一節 材料介紹 28 第二節 分離流程 30 第三節 實驗儀器 37 第四節 實驗溶劑及矽膠 39 第五節 化合物之結構鑑定解析方法 40 第三章 實驗結果 41 第一節 化合物1之結構解析 41 第二節 化合物2之結構解析 51 第三節 化合物3之結構解析 61 第四節 化合物4之結構解析 70 第五節 化合物5之結構解析 80 第六節 化合物6之結構解析 89 第七節 化合物7之結構解析 98 第八節 化合物8之結構 106 第九節 化合物9之結構 107 第十節 化合物10之結構 108 第十一節 生合成探討 109 第十二節 生物活性評估 111 第四章 結論 117 參考文獻 119 圖目錄 圖一、紅果椌木(Dysoxylum hongkongense)之枝葉外觀 29 圖二、紅果椌木(D. hongkongense)枝葉分離流程 (I) 33 圖三、紅果椌木(D. hongkongense)枝葉分離流程 (II) 34 圖四、紅果椌木(D. hongkongense)枝葉分離流程 (III) 34 圖五、紅果椌木(D. hongkongense)根部分離流程 (IV) 35 圖六、紅果椌木(D. hongkongense)根部分離流程 (V) 36 圖七、紅果椌木(D. hongkongense)根部分離流程 (VI) 36 圖八、化合物1-3生合成路徑推導 109 圖九、化合物4-7生合成路徑推導 110 圖1-1化合物1之COSY及selected HMBC correlations 42 圖1-2化合物1與trans-abienol之比旋光度比較 43 圖1-3化合物1之MM2立體構形與selected NOESY correlations 43 圖1-4化合物1之rear octant剖示圖 44 圖1-5化合物1之1H NMR圖譜 (400 MHz, CDCl3) 46 圖1-6化合物1之13C及DEPT NMR圖譜 (100 MHz, CDCl3) 46 圖1-7化合物1之HSQC圖譜 (400 MHz, CDCl3) 47 圖1-8化合物1之HMBC圖譜 (400 MHz, CDCl3) 47 圖1-9化合物1之COSY圖譜 (400 MHz, CDCl3) 48 圖1-10化合物1之NOESY圖譜 (400 MHz, CDCl3) 48 圖1-11化合物1之HRESIMS光譜 49 圖1-12化合物1之UV光譜 49 圖1-13化合物1之CD光譜 50 圖1-14化合物1之IR光譜 50 圖2-1四氫呋喃與四氫吡喃之化學位移比較 52 圖2-2化合物2之COSY及selected HMBC correlations 53 圖2-3化合物2與13E-8,12-Epoxy-13-labden-15-ol之化學位移比較 53 圖2-4化合物2之MM2立體構形與selected NOESY correlations 54 圖2-5化合物2之1H NMR圖譜 (600 MHz, CDCl3) 56 圖2-6化合物2之13C及DEPT NMR圖譜 (150 MHz, CDCl3) 56 圖2-7化合物2之HSQC圖譜 (600 MHz, CDCl3) 57 圖2-8化合物2之HMBC圖譜 (600 MHz, CDCl3) 57 圖2-9化合物2之COSY圖譜 (600 MHz, CDCl3) 58 圖2-10化合物2之NOESY圖譜 (600 MHz, CDCl3) 58 圖2-11化合物2之HRESIMS光譜 59 圖2-12化合物2之CD光譜 59 圖2-13化合物2之IR光譜 60 圖3-1化合物3之COSY及selected HMBC correlations 62 圖3-2化合物3與8, 13-Epoxy-14-labden-12-ol之化學位移比較 62 圖3-3化合物3之MM2立體構形與selected NOESY correlations 63 圖3-4化合物3之1H NMR圖譜 (600 MHz, CDCl3) 65 圖3-5化合物3之13C及DEPT NMR圖譜 (150 MHz, CDCl3) 65 圖3-6化合物3之HSQC圖譜 (600 MHz, CDCl3) 66 圖3-7化合物3之HMBC圖譜 (600 MHz, CDCl3) 66 圖3-8化合物3之COSY圖譜 (600 MHz, CDCl3) 67 圖3-9化合物3之NOESY圖譜 (600 MHz, CDCl3) 67 圖3-10化合物3之HRESIMS光譜 68 圖3-11化合物3之CD光譜 68 圖3-12化合物3之IR光譜 69 圖4-1化合物4之COSY及selected HMBC correlations 71 圖4-2 A,B環順反式之化學位移比較 71 圖4-3 化合物4之MM2立體構形與selected NOESY correlations 72 圖4-4 α-rotunol與β-rotunol之CD光譜比較 73 圖4-5 六環烯酮之構形比較 73 圖4-6化合物4之1H NMR圖譜 (600 MHz, CDCl3) 75 圖4-7化合物4之13C及DEPT NMR圖譜 (150 MHz, CDCl3) 75 圖4-8化合物4之HSQC圖譜 (600 MHz, CDCl3) 76 圖4-9化合物4之HMBC圖譜 (600 MHz, CDCl3) 76 圖4-10化合物4之COSY圖譜 (600 MHz, CDCl3) 77 圖4-11化合物4之NOESY圖譜 (600 MHz, CDCl3) 77 圖4-12化合物4之HRESIMS光譜 78 圖4-13化合物4之UV光譜 78 圖4-14化合物4之CD光譜 79 圖4-15化合物4之IR光譜 79 圖5-1 化合物5之COSY及selected HMBC correlations 81 圖5-2 化合物5之MM2立體構形與selected NOESY correlations 81 圖5-3化合物5之1H NMR圖譜 (600 MHz, CDCl3) 83 圖5-4化合物5之13C NMR圖譜 (150 MHz, CDCl3) 83 圖5-5化合物5之13C及DEPT NMR圖譜 (50 MHz, CDCl3) 84 圖5-6化合物5之HSQC圖譜 (600 MHz, CDCl3) 84 圖5-7化合物5之HMBC圖譜 (600 MHz, CDCl3) 85 圖5-8化合物5之COSY圖譜 (600 MHz, CDCl3) 85 圖5-9化合物5之NOESY圖譜 (600 MHz, CDCl3) 86 圖5-10化合物5之HRESIMS光譜 86 圖5-11化合物5之UV光譜 87 圖5-12化合物5之CD光譜 87 圖5-13化合物5之IR光譜 88 圖6-1 化合物6之COSY及selected HMBC correlations 90 圖6-2 化合物6之MM2立體構形與selected NOESY correlations 91 圖6-3化合物6之1H NMR圖譜 (600 MHz, CDCl3) 93 圖6-4化合物6之13C NMR圖譜 (150 MHz, CDCl3) 93 圖6-5化合物6之HSQC圖譜 (600 MHz, CDCl3) 94 圖6-6化合物6之HMBC圖譜 (600 MHz, CDCl3) 94 圖6-7化合物6之COSY圖譜 (600 MHz, CDCl3) 95 圖6-8化合物6之NOESY圖譜 (600 MHz, CDCl3) 95 圖6-9化合物6之HRESIMS光譜 96 圖6-10化合物6之UV光譜 96 圖6-11化合物6之CD光譜 97 圖6-12化合物6之IR光譜 97 圖7-1 化合物7之COSY及selected HMBC correlations 98 圖7-2 化合物7之MM2立體構形與selected NOESY correlations 99 圖7-3化合物7之1H NMR圖譜 (600 MHz, CDCl3) 101 圖7-4化合物7之13C及DEPT NMR圖譜 (150 MHz, CDCl3) 101 圖7-5化合物7之HSQC圖譜 (600 MHz, CDCl3) 102 圖7-6化合物7之HMBC圖譜 (600 MHz, CDCl3) 102 圖7-7化合物7之COSY圖譜 (600 MHz, CDCl3) 103 圖7-8化合物7之NOESY圖譜 (600 MHz, CDCl3) 103 圖7-9化合物7之HRESIMS光譜 104 圖7-10化合物7之UV光譜 104 圖7-11化合物7之CD光譜 105 圖7-12化合物7之IR光譜 105 表目錄 表一、文獻發表之三萜類化合物(依年代排列) 5 表二、文獻發表之三萜苷類化合物 8 表三、文獻發表之雙萜類化合物 9 表四、文獻發表之倍半萜類化合物 9 表五、文獻發表之固醇類化合物 10 表六、文獻發表之生物鹼類化合物 10 表七、文獻發表之黃酮類化合物 11 表八、文獻發表之其他化合物 11 表九、化合物1之1H、13C-NMR圖譜資料(CDCl3) 45 表十、化合物2之1H、13C-NMR圖譜資料(CDCl3) 55 表十一、化合物3之1H、13C-NMR光譜資料(CDCl3) 64 表十二、化合物4之1H、13C-NMR圖譜資料(CDCl3) 74 表十三、化合物5之1H、13C-NMR圖譜資料(CDCl3) 82 表十四、化合物6之1H、13C-NMR圖譜資料(CDCl3) 92 表十五、化合物7之1H、13C-NMR圖譜資料(CDCl3) 100 表十六、化合物8之1H、13C-NMR圖譜資料(MeOD) 106 表十七、化合物9之1H、13C-NMR圖譜資料(CDCl3) 107 表十八、化合物10之1H、13C-NMR圖譜資料(CDCl3) 108 表十九、文獻發表labdane類雙萜類之相關活性 111 表二十、文獻發表prenyleudesmane類雙萜類之相關活性 113 表二十一、化合物1-7的癌細胞毒殺測試 115 表二十二、化合物1、2、4、7的抗病毒活性測試 116 | |
| dc.language.iso | zh-TW | |
| dc.subject | 雙?類 | zh_TW |
| dc.subject | 紅果椌木 | zh_TW |
| dc.subject | 倍半?類 | zh_TW |
| dc.subject | 抗發炎與抗癌細胞活性 | zh_TW |
| dc.subject | anti-inflammatory | en |
| dc.subject | Dysoxylum hongkongense | en |
| dc.subject | diterpenoids | en |
| dc.subject | sesquiterpenoids | en |
| dc.subject | labdanes | en |
| dc.subject | prenyleudesmanes | en |
| dc.subject | cytotoxic activities | en |
| dc.title | 紅果椌木枝葉與根部雙萜類成分之研究 | zh_TW |
| dc.title | Diterpenoids from the Twigs, Leaves and Roots of Dysoxylum hongkongense | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 102-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 李水盛(Shoei-Sheng Lee),郭曜豪(Yao-Haur Kuo) | |
| dc.subject.keyword | 紅果椌木,雙?類,倍半?類,抗發炎與抗癌細胞活性, | zh_TW |
| dc.subject.keyword | Dysoxylum hongkongense,diterpenoids,sesquiterpenoids,labdanes,prenyleudesmanes,anti-inflammatory,cytotoxic activities, | en |
| dc.relation.page | 130 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2014-08-19 | |
| 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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