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博碩士論文 etd-0722116-092519 詳細資訊
Title page for etd-0722116-092519
論文名稱
Title
軟珊瑚Sarcophyton trocheliophorum、Paralemnalia thyrsoides與Xenia hicksoni二次代謝物之研究
Studies on the Secondary Metabolites from the Soft Corals Sarcophyton trocheliophorum, Paralemnalia thyrsoides, and Xenia hicksoni
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
545
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
2016-06-30
繳交日期
Date of Submission
2016-08-26
關鍵字
Keywords
仿穗軟珊瑚、花環肉質軟珊瑚、傘軟珊瑚、癌細胞毒殺活性
Sarcophyton trocheliophorum, Xenia hicksoni, cytotoxicity, Paralemnalia thyrsoides
統計
Statistics
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The thesis/dissertation has been browsed 5729 times, has been downloaded 563 times.
中文摘要
本研究共從三種軟珊瑚的有機萃取物中分離與解析具有活性的二次代謝物。從澎湖採集到的花環肉質軟珊瑚(Sarcophyton trocheliophorum)分離出十二個cembrene diterpenoid類化合物,包括五個新化合物1–5和七個已知化合物sarcophytonin F (6)、sarcophytoxide (7)、laevigatol A (8)、sarcophytonin C (9)、sarcophytonin G (10)、17-hydroxysarcophytoxide (11)、lobophynin B (12);從綠島採集到的Paralemnalia thyrsoides分離出八個新decalin-type bicyclic diterpenoid類化合物13–20;從綠島採集到的Xenia hicksoni分離出十二個cadinene sesquiterpenoid化合物,包括九個新化合物21–29和三個已知化合物xenitorins A–C (30–32)。以上化合物的結構是藉由有機光譜分析 (紅外線光譜、質譜、旋光、一維及二維NMR) 以及與已知化合物之文獻比對光譜資料來而確定的。化合物20、22與26經由Mosher酯化反應,確立了絕對立體組態。化合物1、6、7與12對於老鼠血癌細胞(P-388)有毒殺活性;化合物14–16、18、22與27對於人類肺癌細胞(A-549)有毒殺活性;化合物17–23與29對於人類直腸癌細胞(HT-29)有毒殺活性(ED50 ≤ 4 μg/mL)。
Abstract
The study was to isolate and elucidate bioactive secondary metabolites from the organic extracts of three Formosan soft corals. Chromatographic fractionation of organic solubles of Sarcophyton trocheliophorum collected at Penghu led to the isolation of five new compounds (1–5) as well as seven known cembranoids sarcophytonin F (6), sarcophytoxide (7), laevigatol A (8), sarcophytonin C (9), sarcophytoninG (10), 17-hydroxysarcophytoxide (11), and lobophynin B (12). Chromatographic separation of organic solubles of Paralemnalia thyrsoides collected at the Green Island led to the isolation of eight new decalin-type bicyclic diterpenoids (13–20). Chromatographic purification of organic solubles of Xenia hicksoni collected at the Green Island led to the isolation of twelve cadinene sesquiterpenoids, including nine new compounds (21–29), and xenitorins A–C (30–32). The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis (IR, MS, 1D and 2D NMR) and by comparison of their physical data with those of the literatures. Moreover, the absolute configurations of 20, 22 and 26 were established by the application of modified Mosher's esterification. Compounds 1, 6, 7 and 12 displayed cytotoxicity against P-388 cell line. Compounds 14–16, 18, 22 and 27 displayed cytotoxicity against A-549 cell line. Compounds 17–23 and 29 displayed cytotoxicity against HT-29 cell line (ED50 ≤ 4 μg/mL).
目次 Table of Contents
論文審定書 i
謝辭 ii
中文摘要 iii
英文摘要 iv
化合物1–32之化學結構 v
目錄 vi
表次 x
圖次 xii
縮寫對照表 xxvii
壹、緒論 1
一、前言及研究動機與目的 1
二、Sarcophyton屬軟珊瑚二次代謝物研究回顧 2
三、Paralemnalia屬軟珊瑚之二次代謝物研究回顧 19
四、Xenia屬軟珊瑚之二次代謝物研究回顧 22
貳、材料與研究方法 37
一、Sarcophyton trocheliophorum樣品採集及分離流程 37
1. Sarcophyton trocheliophorum樣品採集時間、地點與鑑定 37
2. Sarcophyton trocheliophorum之分類地位 37
3. Sarcophyton trocheliophorum之萃取與分離流程 38
4. Sarcophyton trocheliophorum各化學成分之分離純化 40
(1) PHII03-10-2-6-2-H2 (1)、PHII03-10-2-6-2-H3 (6)、 PHII03-10-2-6-3-H3 (7)之純化分離 41
(2) PHII03-12-3-2-H12-H1 (2)、PHII03-12-3-2-H12-H2 (3)、PHII03-12-3-2-H10 (9)與PHII03-12-3-2-H16 (12)之純化分離
(3) PHII03-14-2-2-H3 (4)、PHII03-14-2-2-H4 (5)、PHII03-14-2-5-H5 (8)、PHII03-14-2-6-H5 (9)、PHII03-14-2-6-H6 (11)、PHII03-14-3-1 (10) 與之純化分離 42
二、Paralemnalia thyrsoides樣品採集及分離流程 44
1. Paralemnalia thyrsoides樣品採集時間、地點與鑑定 44
2. Paralemnalia thyrsoides之分類地位 44
3. Paralemnalia thyrsoides之萃取與分離流程 45
4. Paralemnalia thyrsoides各化學成分之分離純化 47
GN99-L2-2-3-H2 (13)、GN99-L2-4-7-H1 (14)、GN99-L2-3-3-1-H1 (15)、GN99-L2-3-4 (16)、GN99-L2-W-3-3 (17)、GN99-L2-5-3 (18)、GN99-L2-5-4 (19)與GN99-L2-2-2-H2 (20)之純化分離 47
三、Xenia hicksoni樣品培養及分離流程 50
1. Xenia hicksoni樣品採集來源、地點與初步鑑定 50
2. Xenia hicksoni之分類地位 50
3. Xenia hicksoni之萃取與分離流程 51
4. Xenia hicksoni各化學成分之分離純化 53
(1) GN101-1-3-2-7-H1 (24)、GN101-1-3-2-7-H3 (28)、GN101-1-3-3-H2-H2 (27)與GN101-1-3-4-H3-H2 (25)之純化分離 53
(2) GN101-2-6 (21)與GN101-2-8-4 (32)之純化分離 54
(3) GN101-3-6-2-2-H1 (29)與GN101-3-6-2-2-H2-H1 (26)之純化分離 55
(4) GN101-4 (30)之純化分離 55
(5) GN101-6-1-2-3 (31)、GN101-6-3-4-H1 (22)與GN101-6-3-4-H2-3 (23)之純化分離 56
参、化學成分之結構證明 57
一、肉質軟珊瑚Sarcophyton trocheliophorum之化學成分的結構證明 57
1. PHII03-10-2-6-2-H2 (1) 之結構解析 57
2. PHII03-12-3-2-H12-H1 (2)之結構解析 73
3. PHII03-12-3-2-H12-H2 (3)之結構解析 89
4. PHII03-14-2-2-H3 (4)之結構解析 106
5. PHII03-14-2-2-H4 (5)之結構解析 123
6. PHII03-10-2-6-2-H3 (6)之結構判定 140
7. PHII03-10-2-6-3-H3 (7)之結構判定 149
8. PHII03-14-2-5-H5 (8)之結構判定 152
9. PHII03-14-2-6-H5 (9)之結構判定 161
10. PHII03-14-3-1 (10)之結構判定 165
11. PHII03-14-2-6-H6 (11)之結構判定 169
12. PHII03-12-3-2-H16 (12)之結構判定 173
二、仿穗軟珊瑚Paralemnalia thyrsoides之化學成分的結構證明 182
1. GN99-L2-2-3-H2 (13)之結構解析 182
2. GN99-L2-4-7-H1 (14)之結構解析 204
3. GN99-L2-3-3-1-H1 (15)之結構解析 221
4. GN99-L2-3-4 (16)之結構解析 239
5. GN99-L2-W-3-3 (17)之結構解析 256
6. GN99-L2-5-3 (18)之結構解析 273
7. GN99-L2-5-4 (19)之結構解析 292
8. GN99-L2-2-2-H2 (20)之結構解析 310
三、傘軟珊瑚Xenia hicksoni之化學成分的結構證明 332
1. GN101-2-6 (21)之結構解析 332
2. GN101-6-3-4-H1 (22)之結構解析 348
3. GN101-6-3-4-H2-3 (23)之結構解析 373
4. GN101-1-3-2-7-H1 (24)之結構解析 389
5. GN101-1-3-4-H3-H2 (25)之結構解析 405
6. GN101-3-6-2-2-H2-H1 (26)之結構解析 420
7. GN101-1-3-3-H2-H2 (27)之結構解析 440
8. GN101-1-3-2-7-H3 (28)之結構解析 455
9. GN101-3-6-2-2-H1 (29)之結構解析 470
10. GN101-4 (30)之結構判定 485
11. GN101-6-1-2-3 (31)之結構判定 489
12. GN101-2-8-4 (32)之結構判定 493
肆、生物活性之測試 497
一、細胞毒殺試驗方法 497
二、MTT分析原理 497
三、活性試驗結果 498
伍、結論 501
陸、參考文獻 503
柒、附錄 515
一、Mosher醯化反應的原理與製備 515
二、實驗設備儀器及材料 516
1.實驗設備儀器 516
2.實驗材料 517
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