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博碩士論文 etd-0730116-142042 詳細資訊
Title page for etd-0730116-142042
論文名稱
Title
台灣產軟珊瑚 Briareum sp. 所含天然物之研究
Study on the Natural Products from the Formosan Soft Coral Briareum sp.
系所名稱
Department
畢業學年期
Year, semester
語文別
Language
學位類別
Degree
頁數
Number of pages
129
研究生
Author
指導教授
Advisor
召集委員
Convenor
口試委員
Advisory Committee
口試日期
Date of Exam
2016-07-14
繳交日期
Date of Submission
2016-08-30
關鍵字
Keywords
Briareum sp.、絕對立體、細胞毒殺、eunicellin、抗發炎
Briareum sp., absolute structure, cytotoxicity, eunicellin, anti-inflammatory
統計
Statistics
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The thesis/dissertation has been browsed 5673 times, has been downloaded 20 times.
中文摘要
七個新雙萜化合物 briarenones A-C (1-3) 和 briarols A-D (4-7),從台東基翬漁港採集而來的軟珊瑚 Briareum sp.中分離出來。這些化合物的結構是由光譜數據分析 (IR, MS, 1H NMR, 13C NMR, HSQC, HMBC, COSY, and NOESY),並比對文獻上已知化合物之光譜數據而定的。化合物1同時利用X-ray單晶繞射得到絕對立體。Eunicellin系列化合物中,化合物4-7的結構較少見,是由於從C-2與 C-7連接組成六元環。
化合物1-7對HT-29、DLD-1、Hucc-T1等進行細胞毒殺活性測試,但其結果並沒有活性。同時將1-3進行抗發炎活性測試,但是也沒有活性呈現。
Abstract
Seven new diterpenoids, briarenones A-C (1-3) and briarols A-D (4-7), have been isolated from the soft coral Briareum sp. which was collected from Jihui Fish Port of Taitung. Their structures were determined through extensive analysis of spectroscopic data (IR, MS, 1H NMR, 13C NMR, HSQC, HMBC, COSY, and NOESY) and by comparison of the NMR spectral data with those of the known compounds. Compound 1 could do X-ray single crystal diffraction to determine the absolute configuration. The structures of 4-7 are not common to the presence of a six-member rings constituted from C2-C7 in eunicellin type compound .
The results for compounds 1–7 in cytotoxicity activity to HT-29, DLD-1, and Hucc-T1 showed no activity. We also did the test of anti-inflammatory activity for compounds 1-3.We also do the test of anti-inflammatory activity for compounds 1-3, but they were still showed no activity.
目次 Table of Contents
目 錄
論文審定書 i
致謝 ii
中文摘要 iii
英文摘要 iv
化合物17 化學結構 v
圖次 viii
表次 xiii
第一章、緒論
第一節、前言 1
第二節、研究背景及目的 2
第三節、文獻回顧 3
第二章、生物材料與研究方法
第一節、Briareum sp. 樣品採集時間、地點 9
第二節、Briareum sp. 生物分類地位 9
第三節、Briareum sp. 實驗分離流程 10
第四節、實驗儀器與材料 12
第三章、化合物之結構證明
第一節、軟珊瑚Briareum sp. 分離出之化合物的結構解析 14
(一)、Briarenone A (1) 結構之解析 14
(二)、Briarenone B (2) 結構之解析 26
(三)、Briarenone C (3) 結構之解析 36
(四)、Briarol A (4) 結構之解析 47
(五)、Briarol B (5) 結構之解析 64
(六)、Briarol C (6) 結構之解析 74
(七)、Briarol D (7) 結構之解析 84
第二節、化合物物理性質及圖譜數據整理 94
第三節、化合物結晶資料 96
第四章、生物活性試驗與結果 106
第一節、生物活性試驗方法 106
第二節、生物活性試驗結果 119
第五章、結論 111
第六章、參考文獻 113
參考文獻 References
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2. 何立德,王鑫,戴昌鳳,台灣的珊瑚礁,遠足文化,2014,60-65
3. Kaveh S.-N.; Ofwegen van L.P.; “Overview of the genus Briareum (Cnidaria, Octocorallia, Briareidae) in the Indo-Pacific, with the description of a new species.” ZooKeys 2016, 557,1–44
4. Wang G.-H.; Sheu J.-H.; Chiang M. Y.; Lee T.-J. “Pachyclavulariaenones A-C, three novel diterpenoids from the soft coral Pachyclavularia violacea” Tetrahedron Lett. 2001, 42 ,2333–2336
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7. Abimael D. R.; Oscar M. C. “The Briarellins, new Eunicillin-based Diterpenoids from a Caribbean Gorgonian, Briareum asbestinum.” Tetrahedron 1995, 25, 6869-6880
8. Abimael D. R.; Oscar M. C. “Studies on the minor constituents of the Caribbean gorgonian octocorol Briareum asbestinum PALLAS. Isolation snd structure determination of the eunicillin-based diterpenoids briarellins E-I.” Chem. Pharm. Bull. 1995, 43, 1853-1858
9. Olivier C.; Larry E. O.; Lewis D. P. “Enantioselective Total Synthesis of Briarellins E and F: The First Total Syntheses of Briarellin Diterpenes” J. AM. CHEM. SOC. 2003, 125, 6650-6652
10. Claudia A. O.; Abimael D. R.; Eduardo O.-B.; Todd L. C. “Briarellins J-P and Polyanthellin A: New Eunicellin-Based Diterpenes from the Gorgonian Coral Briareum polyanthes and Their Antimalarial Activity” J. Nat. Prod. 2003, 66, 357-363
11. Michael T. C.; Mark C. M.; Abimael D. R. “Total Synthesis of the Proposed Structure of Briarellin J.” Org Lett. 2010, 12, 5028-5031
12. Friedrich, D.; Doskotch, R.-W.; Paquette, L.-A. “Revised Constitution of Sclerophytin A and B.” Org. Lett. 2000, 2, 1879-1882
13. Hassan, H.-M.; Khanfar, M.-A.; Elnagar, A.-Y.: Mohammed, R.; Shaala, L.-A.; Youssef, D.-T.-A.; Hifnawy, M.-S.; El Sayed, K.-A. “Pachycladin A-E, Prostate Cancer Invasion and Migration Inhibitory Eunicellin-Based Diterpenoids from the Red Sea Soft Coral Cladiella pachyclados.” J. Nat. Prod. 2010, 73, 848-853
14. Zhao, K.; Wang, Y.; Han, L. “4,5-Epoxycholestane-3,6-diols: Templates for generating the full set of eight cholestane-3,5,6-triol stereoisomers in multigram scales, but not for a cholestane-3,5,6-triol.” Steroids 2007, 72, 95-104
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