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博碩士論文 etd-0830101-160037 詳細資訊
Title page for etd-0830101-160037
論文名稱
Title
臺灣產海綿生物活性成分研究
STUDIES ON BIOACTIVE CONSTITUENTS FROM SELECTED TAIWANESE MARINE SPONGES
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
174
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
2001-07-26
繳交日期
Date of Submission
2001-08-30
關鍵字
Keywords
海綿
sponge
統計
Statistics
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中文摘要
中 文 摘 要

海綿是一種富含活性新物質的海洋生物。本實驗篩選了數種由南台灣海域所採集的台灣產海綿,一共分離得到九個新的化合物,其中包括一個具新骨幹結構的天然物。研究的過程中,分別由沈氏擬金海綿 (Parahigginsia sheni) 中分離得到六個新的倍半
Abstract
ABSTRACT

Marine sponges have proved to be a rich source of new bioactive products. In our screening of several species of Taiwanese marine sponges from southern coast of Taiwan, we have isolated nine new compounds in which one has a new carbon skeleton. Investigation of the marine sponge Parahigginsia sp. has resulted in the isolation of six new sesquiterpenes, parahigginols A-D (59-62), parahigginine (63) and para- higginic acid (65). Two new sesquiterpenes hydroquinones, hippochro- mins A and B (71, 72) were isolated from the marine sponge Hippo- spongia metachromia. In addition, an unstable, novel meroditerpenoid, strongdurin (76), which might be a precursor of strongylophorins, was isolated from the sponge Strongylophora durissima. Moreover study of the secondary metabolites of sponge Theonella cf. swinhoei, four trideca- peptide lactones theonellapeptolides Ia-Id (44-47) and one dimeric ma- crolide swinholide A (49), were also isolated and their structures were determined. The structures of these compounds and their derivatives were established primarily on the basis of their spectral analysis and chemical derivatization. The application of NMR techniques included 1H, 13C NMR, DEPT, COSY, HMQC, HMBC, NOESY and so on.

Biological studies revealed that parahigginols A-D (59-62), parahig- ginine (63), parahigginone (64) and parahigginic acid (65), exhibited in vitro cytotoxicity against mouse leukemia cells (P-388) and human mouth epidermoid carcinoma (KB16), lung carcinoma (A549) and colon carci- noma (HT-29) cancer cells. Compounds 60-65 exhibited moderate activity with IC50 value greater than 1 μg/mL, while parahigginol A (59) was inactive. In our measurement, strongdurin monomethylate (77), which isolated from the marine sponge Strongylophora durissima, was mild cytotoxicity against human mouth epidermoid carcinoma (KB16) and hepatoma carcinoma (Hepa) cell lines with IC50 values of 6.7 and 8.7 μg/mL. Compounds 13, 14, 68 and 69, which isolated from the marine sponge Hippospongia metachromia, exhibited potent cytotoxicity against human colon (COLO-250) tumor cells at concentrations of 0.10, 0.26, 0.53 and 0.22 μg/mL, respectively. Theonellapeptolides Ia-Ib (44-45) and swinholide A (49), which isolated from the marine sponge Theonella cf. swinhoei, showed significant cytotoxicity against above NUGC and HONE-1 cell lines at concentrations of 50 μg/mL, but were inactive at 10 μg/mL.
目次 Table of Contents
目 錄
頁次
第一部份 緒論
第一章 前言………………………………………………………….…1
第二章 研究動機及展望…………………………………………….…3
第三章 相關化合物之研究回顧
第一節 沈氏擬金海綿(Parahigginsia sheni)部分………………....5
第二節 紫色馬形海綿(Hippospongia metachromia)部分………...7
第三節 硬殼圓枝海綿(Strongylophora durissima)部分…………..9
第四節 隋氏地殼海綿(Theonella swinhoei)部分………………...14

第二部份 材料與方法
第一章 樣品的採集
第一節 沈氏擬金海綿(Parahigginsia sheni)部分………………..20
第二節 紫色馬形海綿(Hippospongia metachromia)部分………..21
第三節 硬殼圓枝海綿(Strongylophora durissima)部分………….22
第四節 隋氏地殼海綿(Theonella swinhoei)部分……………...…23
第二章 分離與純化
第一節 沈氏擬金海綿(Parahigginsia sheni)部分……………......24
第二節 紫色馬形海綿(Hippospongia metachromia)部分………..26
第三節 硬殼圓枝海綿(Strongylophora durissima)部分………….28
第四節 隋氏地殼海綿(Theonella swinhoei)部分………………...30
第三章 結構之鑑定
第一節 儀器部分………………………………………………….32
第二節 矽膠與溶劑部分………………………………………….33
第四章 衍生物之製備
一、 甲基化反應 (Methylation)……………………………..34
二、 乙醯基化反應 (Acetylation)………………………...…34
第五章 生物活性之篩選………………………………………………35

第三部份 結果與討論
第一章 沈氏擬金海綿(Parahigginsia sheni)部分
Parahigginol A (59) 之結構解析……………………………...37
Parahigginol B (60) 之結構解析……………………………...42
Parahigginol C (61) 之結構解析……………………………...48
Parahigginol D (62) 之結構解析……………………………...54
Parahigginine (63) 之結構解析………………………….……60
Parahigginone (64) 之結構解析………………………………65
Parahigginic acid (65) 之結構解析…………………………...70
第二章 紫色馬形海綿(Hippospongia metachromia)部分
Hippochromin A (71) 之結構解析……………………………80
Hippochromin B (72) 之結構解析……………………………89
第三章 硬殼圓枝海綿(Strongylophora durissima)部分
Strongdurin (76) 之化學結構鑑定…………….………….....104
第四章 隋氏地殼海綿(Theonella swinhoei)部分
Theonellapeptolide Ia (44) 之結構解析……………………..117
Theonellapeptolide Ib (45) 之結構解析……………………..120
Theonellapeptolide Ic (46) 之結構解析……………………..123
Theonellapeptolide Id (47) 之結構解析……………………..125
Swinholide A (49) 之結構解析……………………………...129
第五章 活性測試結果
第一節 沈氏擬金海綿(Parahigginsia sheni)部分………..……..147
第二節 紫色馬形海綿(Hippospongia metachromia)部分………148
第三節 硬殼圓枝海綿(Strongylophora durissima)部分………...149
第四節 隋氏地殼海綿(Theonella swinhoei)部分……………….150

第四部分 結論……………………………………………………154
第五部分 參考文獻…………………………………………...…..159
附錄一、個人資料表
一、 基本資料…………………………………………….……..167
二、 主要學歷……………………………………………….…..167
附錄二、研究成果目錄
一、 期刊論文……………………………..……………………168
二、 研討會論文………………………..………………………171
附錄三、顯色劑………………………………………………………174












圖 目 錄
頁次
圖一、沈氏擬金海綿(Parahigginsia sheni)的外觀………….………...21
圖二、紫色馬形海綿(Hippospongia metachromia)的外觀…………….22
圖三、硬殼圓枝海綿(Strongylophora durissima)的外觀………………23
圖四、隋氏地殼海綿(Theonella swinhoei)的外觀…………………….24
圖五、沈氏擬金海綿(Parahigginsia sheni)的分離流程………………25
圖六、紫色馬形海綿(Hippospongia metachromia)的分離流程……...27
圖七、硬殼圓枝海綿(Strongylophora durissima)的分離流程………..28
圖八、隋氏地殼海綿(Theonella swinhoei)的分離流程………….……31
圖59-1、Parahigginol A (59) 的1H NMR圖譜………………………39
圖59-2、Parahigginol A (59) 的IR光譜圖………………………...…40
圖59-3、Parahigginol A (59) 的EIMS質譜圖…………………...…..40
圖60-1、Parahigginol B (60) 的1H NMR圖譜…………………..…..44
圖60-2、Parahigginol B (60) 的13C NMR圖譜………………..…….44
圖60-3、Parahigginol B (60) 的HMQC圖譜…………….…….…….45
圖60-4、Parahigginol B (60) 的HMBC圖譜………………….……..45
圖60-5、Parahigginol B (60) 的COSY圖譜…………………………46
圖60-6、Parahigginol B (60) 的IR光譜圖…………………………...46
圖60-7、Parahigginol B (60) 的EIMS質譜圖………………………..47
圖61-1、Parahigginol C (61) 的1H NMR圖譜……………………….50
圖61-2、Parahigginol C (61) 的13C NMR圖譜………………………50
圖61-3、Parahigginol C (61) 的DEPT圖譜………………………….51
圖61-4、Parahigginol C (61) 的COSY圖譜………………………….51
圖61-5、Parahigginol C (61) 的IR光譜圖……………………………52
圖61-6、Parahigginol C (61) 的EIMS質譜圖………………………..52
圖62-1、Parahigginol D (62) 的HMBC圖譜…………………….……56
圖62-2、Parahigginol D (62) 的1H NMR圖譜……………………….57
圖62-3、Parahigginol D (62) 的13C NMR圖譜………………………57
圖62-4、Parahigginol D (62) 的HMQC圖譜…………………………58
圖62-5、Parahigginol D (62) 的COSY圖譜…………………………58
圖62-6、Parahigginol D (62) 的IR光譜圖…………………………..59
圖62-7、Parahigginol D (62) 的EIMS質譜圖………………………59
圖63-1、Parahigginine (63) 的1H NMR圖譜………………………...62
圖63-2、Parahigginine (63) 的13C NMR圖譜………………………..62
圖63-3、Parahigginine (63) 的DEPT圖譜……………………………63
圖63-4、Parahigginine (63) 的IR光譜圖……………………………..63
圖63-5、Parahigginine (63) 的EIMS質譜圖…………………………64
圖64-1、Parahigginone (64) 的1H NMR圖譜……………………….67
圖64-2、Parahigginone (64) 的13C NMR圖譜………………………67
圖64-3、Parahigginone (64) 的DEPT圖譜…………………………..68
圖64-4、Parahigginone (64) 的IR光譜圖……………………………68
圖64-5、Parahigginone (64) 的EIMS質譜圖………………………..69
圖65-1、Parahigginic acid (65) 的1H NMR圖譜…………………….71
圖65-2、Parahigginic acid (65) 的13C NMR圖譜……………………72
圖65-3、Parahigginic acid (65) 的DEPT圖譜……………………….72
圖65-4、Parahigginic acid (65) 的IR光譜圖…………………………73
圖65-5、Parahigginic acid (65) 的EIMS質譜圖………………………73
圖九、Hippochromin A diacetate (69) HMBC的關聯……………….…82
圖69-1、Hippochromin A diacetate (69) 的1H NMR圖譜…………...84
圖69-2、Hippochromin A diacetate (69) 的13C NMR圖譜…………..84
圖69-3、Hippochromin A diacetate (69) 的DEPT圖譜………………85
圖69-4、Hippochromin A diacetate (69) 的HMQC圖譜…………….85
圖69-5、Hippochromin A diacetate (69) 的HMBC圖譜…………….86
圖69-6、Hippochromin A diacetate (69) 的COSY圖譜……………..86
圖69-7、Hippochromin A diacetate (69) 的NOESY圖譜……………87
圖69-8、Hippochromin A diacetate (69) 的IR光譜圖……………….87
圖69-9、Hippochromin A diacetate (69) 的FABMS質譜圖…………88
圖十、Hippochromin B diacetate (70) HMBC的關聯………………….91
圖70-1、Hippochromin B diacetate (70) 的1H NMR圖譜…………..92
圖70-2、Hippochromin B diacetate (70) 的13C NMR圖譜………….92
圖70-3、Hippochromin B diacetate (70) 的HMQC圖譜…………….93
圖70-4、Hippochromin B diacetate (70) 的HMBC圖譜…………….93
圖70-5、Hippochromin B diacetate (70) 的COSY圖譜……………..94
圖70-6、Hippochromin B diacetate (70) 的NOESY圖譜……………94
圖70-7、Hippochromin B diacetate (70) 的IR光譜圖……………….95
圖70-8、Hippochromin B diacetate (70) 的FABMS質譜圖………...95
圖十一、Strongdurin monomethylate (77) HMBC的關聯……………106
圖76-1、Strongdurin (76) 的1H NMR圖譜………………………….108
圖76-2、Strongdurin (76) 的13C NMR圖譜………………………..108
圖77-1、Strongdurin monomethylate (77) 的1H NMR圖譜………..109
圖77-2、Strongdurin monomethylate (77) 的13C NMR圖譜……….109
圖77-3、Strongdurin monomethylate (77) 的DEPT圖譜……………110
圖77-4、Strongdurin monomethylate (77) 的COSY圖譜…………..110
圖77-5、Strongdurin monomethylate (77) 的HMQC圖譜………….111
圖77-6、Strongdurin monomethylate (77) 的HMBC圖譜………….111
圖77-7、Strongdurin monomethylate (77) 的NOESY圖譜………..112
圖77-8、Strongdurin monomethylate (77) 的IR光譜圖……………112
圖78-1、Strongdurin dimethylate (78) 的1H NMR圖譜…………….113
圖78-2、Strongdurin dimethylate (78) 的13C NMR圖譜……………113
圖44-1、Theonellapeptolide Ia (44) 的1H NMR圖譜……………….118
圖44-2、Theonellapeptolide Ia (44) 的13C NMR圖譜………………118
圖44-3、Theonellapeptolide Ia (44) 的COSY圖譜…………………119
圖44-4、Theonellapeptolide Ia (44) 的HMQC圖譜…………………119
圖45-1、Theonellapeptolide Ib (45) 的1H NMR圖譜……………….120
圖45-2、Theonellapeptolide Ib (45) 的13C NMR圖譜………………121
圖45-3、Theonellapeptolide Ib (45) 的COSY圖譜…………………121
圖45-4、Theonellapeptolide Ib (45) 的HMQC圖譜…………………122
圖45-5、Theonellapeptolide Ib (45) 的HMBC圖譜…………………122
圖46-1、Theonellapeptolide Ic (46) 的1H NMR圖譜………………124
圖46-2、Theonellapeptolide Ic (46) 的13C NMR圖譜………………124
圖47-1、Theonellapeptolide Id (47) 的1H NMR圖譜……………….126
圖47-2、Theonellapeptolide Id (47) 的COSY圖譜………………….126
圖47-3、Theonellapeptolide Id (47) 的13C NMR圖譜………………127
圖47-4、Theonellapeptolide Id (47) 的DEPT圖譜………………….127
圖47-5、Theonellapeptolide Id (47) 的HMQC圖譜………………..128
圖47-6、Theonellapeptolide Id (47) 的HMBC圖譜…………………128
圖49-1、Swinholide A (49) 的1H NMR圖譜……………………….130
圖49-2、Swinholide A (49) 的13C NMR圖譜………………………130
圖49-3、Swinholide A (49) 的COSY圖譜………………………….131
圖49-4、Swinholide A (49) 的HMQC圖譜…………………………131
圖49-5、Swinholide A (49) 的HMBC圖譜………………………...132
圖十二、Swinholide A (49) 的 1H NMR數據指定…………………133
圖十三、Swinholide A (49) 的 13C NMR數據指定…………………134
























表 目 錄
頁次
表1、化合物Parahigginols A-D (59-62) 的1H NMR數據指定
…………………………………………………………………74
表2、化合物Parahigginols A-D (59-62) 的13C NMR數據指定
…………………………………………………………………75
表3、化合物Parahigginine (63),Parahigginone (64) 及Parahigginic acid (65) 的1H NMR數據指定….……………….…………76
表4、化合物Parahigginine (63),Parahigginone (64) 及Parahigginic acid (65) 的13C NMR數據指定….……………….………...77
表5、化合物metachromins A、B及E (13、14、17) 的1H NMR
數據指定………………………………………………………97
表6、化合物metachromins A、B及E (13、14、17) 的13C NMR
數據指定………………………………………………………98
表7、化合物Hippochromin B (72)、Hippochromin A diacetate (69) 和Hippochromin B diacetate (70) 的1H NMR數據指定.…
………………………………………………………………....99
表8、化合物Hippochromin B (72)、Hippochromin A diacetate (69) 和Hippochromin B diacetate (70) 的13C NMR數據指定……
………………………………………………………………..100
表9、化合物Strongdurin (76)、Strongdurin monomethylate (77) 及Strongdurin dimethylate (78) 的1H NMR數據指定.………….
………………………………………………………………...114
表10、化合物Strongdurin (76)、Strongdurin monomethylate (77) 及Strongdurin dimethylate (78) 的13C NMR數據指定.………….
………………………………………………………………...115
表11、化合物Theonellapeptolides Ia-Id (44-47) 的1H NMR數據
指定.………………………………………………………..136
表12、化合物Theonellapeptolides Ia-Id (44-47) 的13C NMR數據
指定.………………………………………………………..142
表13、細胞毒殺活性測試結果………………………………….…147
表14、細胞毒殺活性測試結果………………………………….…148
表15、細胞毒殺活性測試結果………………………………….…149
表16、細胞毒殺活性測試結果………………………………….…151


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