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論文名稱 Title |
綠島產肥厚肉質、美麗肉質及花環肉質軟珊瑚
化學成分及癌細胞毒殺活性之研究
Chemical Constituents and Cytotoxicity of Soft Corals Sarcophyton crassocaule, Sarcophyton elegans and Sarcophyton trocheliophorum |
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系所名稱 Department |
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畢業學年期 Year, semester |
語文別 Language |
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學位類別 Degree |
頁數 Number of pages |
131 |
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研究生 Author |
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指導教授 Advisor |
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召集委員 Convenor |
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口試委員 Advisory Committee |
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口試日期 Date of Exam |
1999-07-14 |
繳交日期 Date of Submission |
2000-06-09 |
關鍵字 Keywords |
癌細胞毒殺活性、肥厚肉質軟珊瑚、花環肉質軟珊瑚、美麗肉質軟珊瑚 Sarcophyton trocheliophorum, soft corals, Sarcophyton elegans, cytotoxicity, Sarcophyton crassocaule |
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統計 Statistics |
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中文摘要 |
綠島產肥厚肉質軟珊瑚 (Sarcophyton crassocaule) 之二氯甲烷萃取物分離純化後,共得到三個diterpenoid化合物,分別為:(1S*, 3R*, 4R*, 7E, 11E, 14R*)-3, 4-epoxycembra-7, 11, 15-trien-1, 14-olide (1)、(1R*, 3E, 7E,11R*, 12S*, 14R*)-11, 12-epoxycembra-3, 7, 15-trien-1, 14-olide (2)、(1R*, 2S*, 3E, 7S*, 8R*, 11S*, 12Z)-8, 11-epidioxy-7-acetoxycembra-3, 12, 15-trien-1, 2-olide (3),以及二個steroid化合物,分別為:(24S)-24-methylcholestane-3b, 5a, 6b-triol (4) 與24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5)。其中化合物1與2是新化合物,而化合物3為海洋天然物少見之含cyclic peroxide化合物。 綠島產美麗肉質 (S. elegans) 及花環肉質 (S. trocheliophorum) 軟珊瑚之二氯甲烷萃取物分離純化後,從美麗肉質軟珊瑚中分離到24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) 之steroid化合物,從花環肉質軟珊瑚中分離到 (+)-isosarcophine (6) 之diterpenoid化合物。 另外,由未知屬名之八放珊瑚 (編號CD01) 中,共分離到二個steroid化合物,分別為:cholesterol (7) 及 (22E, 24S)-24-methylcholesta- 5, 22-dien-3b-ol (8)。 上述之化合物經癌細胞毒殺活性測試後,化合物1-4、6及7對P388具有選擇性抑制作用,而化合物2和5則對HT-29有選擇性抑制。 |
Abstract |
Chromatographic purification of a methylene chloride extract of Formosan soft coral Sarcophyton crassocaule (collected in Green island) led to the isolation of two new (1S*, 3R*, 4R*, 7E, 11E, 14R*)-3, 4-epoxycembra-7, 11, 15-trien-1, 14-olide (1) and (1R*, 3E, 7E,11R*, 12S*, 14R*)-11, 12-epoxycembra-3, 7, 15-trien-1, 14-olide (2) isomeric diterpenoids , a known cyclic peroxide diterpenoid (1R*, 2S*, 3E, 7S*, 8R*, 11S*, 12Z)-8, 11-epidioxy-7-acetoxycembra-3, 12, 15-trien-1, 2-olide (3), as well as two known (24S)-24-methylcholestane-3b, 5a, 6b-triol (4) and 24x-methyl-cholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) steroids. Chromatographic fractionation of a methylene chloride extract of two Formosan soft corals Sarcophyton elegans (collected in Green island) led to the isolation of a known 24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) steroid, the methylene chloride extract of Sarcophyton trocheliophorum, on the other hand, afforded a known diterpenoid, (+)-isosarcophine (6). Purification of a methylene chloride extract of Octocorallia soft coral (unidentified) led to the isolation of two known steroids, cholesterol (7) and (22E, 24S)-24-methylcholesta-5, 22-dien-3b-ol (8). Compounds 1-7 exhibited cytotoxicity against P388 cancer cell line. Compounds 2 and 5 were active against HT-29 cancer cell line. |
目次 Table of Contents |
壹、緒論…………………………………………………………………12 一、 前言…………………………………………………………12 二、 曾由Sarcophyton屬軟珊瑚中分離到之化合物…………… 14 三、 過去由Sarcophyton屬軟珊瑚所分離到之有生物活性二次代謝物………………………………………………………25 四、 研究動機及目的……………………………………………26 貳、Sarcophyton crassocaule軟珊瑚化學成分之研究………………27 一、 採集及分類地位……………………………………………27 二、 Sarcophyton crassocaule軟珊瑚之萃取與分離…………28 三、 Sarcophyton crassocaule軟珊瑚化學成分之分離純化……31 (1) GN26-203 (1) 之分離純化…………………………….31 (2) GN26-204 (2) 之分離純化………………………………33 (3) GN26-206 (3) 之分離純化………………………………35 (4) GN26-16K (4) 之分離純化……………………………37 四、 Sarcophyton crassocaule軟珊瑚化學成分之結構解析……40 (1) GN26-203 (1) 之結構解析………………………………40 (2) GN26-204 (2) 之結構解析………………………………52 (3) GN26-206 (3) 之結構解析………………………………63 (4) GN26-16K (4) 之結構解析……………………………74 參、Sarcophyton elegans軟珊瑚化學成分之研究……………………79 一、 採集及分類地位……………………………………………79 二、 Sarcophyton elegans軟珊瑚之萃取與分離…………………80 三、 Sarcophyton elegans軟珊瑚化學成分之分離純化………….82 (1) GN07-53K (5) 之分離純化……………………………..82 四、 Sarcophyton elegans軟珊瑚化學成分之結構解析…………85 (1) GN07-53K (5) 之結構解析……………………………85 肆、Sarcophyton trocheliophorum軟珊瑚化學成分之研究……………90 一、 採集及分類地位……………………………………………90 二、 Sarcophyton trocheliophorum軟珊瑚之萃取與分離………91 三、 Sarcophyton trocheliophorum軟珊瑚化學成分之分離純化…………………………………………………………….93 (1) GN11-97 (6) 之分離純化………………………………93 四、 Sarcophyton trocheliophorum軟珊瑚化學成分之結構解析……………………………………………………………95 (1) GN11-97 (6) 之結構解析………………………………..95 伍、編號CD01八放珊瑚化學成分之研究……………………………99 一、 採集及分類地位……………………………………………..99 二、 編號CD01八放珊瑚之萃取與分離………………………100 三、 編號CD01八放珊瑚化學成分之分離純化……………….102 (1) CD01-104K (7) 之分離純化……………………………102 (2) CD01-106K (8) 之分離純化……………………………104 四、 編號CD01八放珊瑚化學成分之結構解析………………107 (1) CD01-104K (7) 之結構解析……………………………107 (2) CD01-106K (8) 之結構解析……………………………111 陸、化合物之癌細胞毒殺活性………………………………………115 柒、結論………………………………………………………………116 捌、參考文獻…………………………………………………………118 玖、附錄………………………………………………………………127 一、 使用儀器及藥品……………………………………………127 二、 癌細胞毒殺活性測試之分析方法…………………………129 三、 MTT分析原理……………………………………………130 圖目錄 頁次 圖一、本研究所分離到之成分…………………………………………3 圖二、Sarcophyton crassocaule軟珊瑚所分離到之化學成分………29 圖三、Sarcophyton crassocaule軟珊瑚之分離流程………………….. 30 圖四、GN26-203 (1) 之1H-NMR圖譜…………………………………44 圖五、GN26-203 (1) 之13C-NMR及DEPT圖譜……………………45 圖六、GN26-203 (1) 之HMQC圖譜…………………………………46 圖七、GN26-203 (1) 之COSY圖譜……………………………………47 圖八、GN26-203 (1) 之HMBC圖譜…………………………………...48 圖九、GN26-203 (1) 之HMBC關聯圖………………………………...49 圖十、GN26-203 (1) 之NOESY圖譜…………………………………50 圖十一、GN26-203 (1) 之NOESY關聯圖……………………………51 圖十二、GN26-204 (2) 之1H-NMR圖譜………………………………55 圖十三、GN26-204 (2) 之13C-NMR及DEPT圖譜……………………56 圖十四、GN26-204 (2) 之HMQC圖譜………………………………..57 圖十五、GN26-204 (2) 之COSY圖譜…………………………………58 圖十六、GN26-204 (2) 之HMBC圖譜………………………………59 圖十七、GN26-204 (2) 之HMBC關聯圖……………………………60 圖十八、GN26-204 (2) 之NOESY圖譜………………………………61 圖十九、GN26-204 (2) 之NOESY關聯圖……………………………62 圖二十、GN26-206 (3) 之1H-NMR圖譜………………………………66 圖二十一、GN26-206 (3) 之13C-NMR及DEPT圖譜…………………67 圖二十二、GN26-206 (3) 之HMQC圖譜…………………………….68 圖二十三、GN26-206 (3) 之COSY圖譜………………………………69 圖二十四、GN26-206 (3) 之HMBC圖譜………………………….…70 圖二十五、GN26-206 (3) 之HMBC關聯圖……………………….…71 圖二十六、GN26-206 (3) 之NOESY圖譜………………………….…72 圖二十七、GN26-206 (3) 之NOESY關聯圖…………………………73 圖二十八、GN26-16K (4) 之1H-NMR圖譜………………………….76 圖二十九、GN26-16K (4) 之13C-NMR及DEPT圖譜…………….…77 圖三十、Sarcophyton elegans軟珊瑚所分離到之化學成分………….80 圖三十一、Sarcophyton elegans軟珊瑚之分離流程………………….81 圖三十二、GN07-53K (5) 之1H-NMR圖譜…………………………87 圖三十三、GN26-18K (5) 之1H-NMR圖譜……………………….…88 圖三十四、GN07-53K (5) 之13C-NMR及DEPT圖譜………………89 圖三十五、Sarcophyton trocheliophorum軟珊瑚所分離到之化學成分………………………………………………………….91 圖三十六、Sarcophyton trocheliophorum軟珊瑚之分離流程………..92 圖三十七、GN11-97 (6) 之1H-NMR圖譜……………………………..97 圖三十八、GN11-97 (6) 之13C-NMR及DEPT圖譜…………………..98 圖三十九、編號CD01八放珊瑚所分離到之化學成分…………100 圖四十、編號CD01八放珊瑚之分離流程……………………….101 圖四十一、CD01-104K (7) 之1H-NMR圖譜………………………109 圖四十二、CD01-104K (7) 之13C-NMR及DEPT圖譜……………110 圖四十三、CD01-106K (8) 之1H-NMR圖譜………………………113 圖四十四、CD01-106K (8) 之13C-NMR及DEPT圖譜……………114 表目錄 頁次 表一、曾由Sarcophyton屬分離到之Cembranoids…………………….14表二、曾由Sarcophyton屬分離到之Steroids………………………….17 表三、化合物4及文獻之13C-NMR化學位移表……………………78 表四、化合物1-8之癌細胞毒殺活性值………………………115 |
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