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研究生:張弘煒
研究生(外文):Hong-Wei Zhang
論文名稱:軟珊瑚Sinularia flexibilis之後續化學組成研究暨養殖型軟珊瑚Sinularia penghuensis與入侵種植物小花蔓澤蘭Mikania micrantha之所含天然物探討
論文名稱(外文):The Follow-up Research of the Chemical Constituents of the Soft Coral Sinularia flexibilis and the Study on Natural Products of the Cultured Soft Coral Sinularia penghuensis and the Invasive Plant Mikania micrantha
指導教授:許志宏許志宏引用關係
指導教授(外文):Jyh-Horng Sheu
學位類別:碩士
校院名稱:國立中山大學
系所名稱:海洋生物科技暨資源學系研究所
學門:自然科學學門
學類:海洋科學學類
論文種類:學術論文
論文出版年:2023
畢業學年度:111
語文別:中文
論文頁數:144
中文關鍵詞:軟珊瑚小花蔓澤蘭萜類黃酮類人類乳腺癌細胞 MDA-MB-231人類非小細胞肺癌細胞 A549登革熱病毒PL046
外文關鍵詞:soft coralMikania micranthaterpenoidsflavonoidhuman breast cancer cells MDA-MB-231human non-small lung cancer cells A549dengue virus PL046
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本次研究是對三種生物材料,包含:養殖型軟珊瑚Sinularia penghuensis、陸上植物小花蔓澤蘭Mikania micrantha的化學物質組成以及軟珊瑚Sinularia flexibilis之化學成分後續研究。由S. flexibilis後續研究中分離得到一個新的cembrane-type的二萜類化合物flexibilone (1)和一個已知cembrane-type的二萜類化合物sinulariolone (2);由S. penghuensis分離得到一個已知倍半萜類化合物(1''E,5''E)-5-(2'',6''-dimethylocta-1'',5'',7''-trienyl) furan-3-carboxylic acid (3);從小花蔓澤蘭M. micrantha分離得到7個已知的化合物分別為黃酮類的mikanin (4)以及倍半萜類的scandenolide (5)、dihydromikanolide (6)、mikanolide (7)、dexoymikanolide (8)和單萜類的cylindrinol D (9)與一個吲哚啉化合物3-hydroxymethyl-6-methoxy-2,3-dihydro-1H-indol-2-ol (10)。本次研究首次建立化合物9的絕對立體構型以及10之相對及絕對立體構型。本次研究所分離的化合物結構及物理性質由詳細的光譜測定和各式光譜數據得出並與先前已知化合物文獻做比對。
將本次研究的部分化合物與粗萃物進行針對人類乳腺癌細胞MDA-MB-231和人類非小細胞肺癌細胞A549之細胞毒殺試驗與對登革熱病毒PL046之病毒抑制測試,研究中發現小花蔓澤蘭的粗萃物對於MDA-MB-231與A549的細胞毒殺活性之半抑制活性(IC50)值分別為16.07±0.90和33.80±0.72 μg/mL,而化合物7和化合物9的IC50值分別為4.17±0.19 和20.10±0.35 與15.17±1.80和36.67±0.78 μM。另外,在登革熱病毒PL046病毒抑制測試的前期研究中發現,化合物6和7對於登革熱病毒PL046具有明顯的抑制作用。
Chemical investigation of three different species, including two soft corals ,Sinularia penghuensis and Sinularia flexibilis, and one terrestrial plant (Mikania micrantha), were carried out. These studies led to the isolation of ten chemical constituents, including a new cembrane-type diterpenoid flexibalone (1) and a known cembrane, sinulariolone (2) from S. flexibilis; a known sesquiterpenoid, (1''E,5''E)-5-(2'',6''-dimethylocta-1'',5'',7''-trienyl)furan-3-carboxylic acid (3), from S. penghuensis; and a known flavonoid mikanin (4), together with five known sesquiterpenoids, scandenolide (5), dihydromikanolide (6), mikanolide (7), dexoymikanolide (8), a known monoterpenoid, cylindrinol D (9), and an indoline-type compound, 3-hydroxymethyl-6-methoxy-2,3-dihydro-1H-indol-2-ol (10), from the M. micrantha. This study established the absolute configuration of 9 and the relative and absolute configurations of 10 for the first time. All chemical structures were established by spectroscopic analyses and comparing with the related physical properties and spectral data of the known compounds.
The crude extracts of S. penghuensis and M. micrantha and some pure compounds have been assayed the cytotoxicity of the human breast cancer cells MDA-MB-231 and human non-small lung cancer cells A549 and the inhibition of dengue virus PL046. In cytotoxicity assay, the crude extract of M. micrantha showed the activities to inhibit the cancer cells MDA-MB-231 and A549 with IC50¬ values 16.07±0.90 μg/mL and 33.80±0.72 μg/mL, respectively. Compounds 7 and 9, isolated from M. micrantha, exhibited the activities against the growth of both cells with IC50¬ values 4.17±0.19 and 20.10±0.35 μM and 15.17±1.80 and 36.67±0.78 μM , respectively. In preliminary inhibition assay of dengue virus PL046, compounds 6 and 7 displayed notable inhibition against protein synthesis of virus in 10 μM of each compound.
論文審定書 i
中文摘要 ii
Abstract iii
化合物1-10結構 v
第一章、 緒論 1
第一節、 前言 1
第二節、 研究動機 2
第三節、 文獻回顧 3
第二章、 生物材料與研究方法 64
第一節、 生物樣本採集、分類地位與研究流程 64
一、 小花蔓澤蘭(Mikania micrantha)的採集和研究方式與生物分類地位 64
二、 養殖型軟珊瑚(Sinularia penghuensis)的採集和研究方式與生物分類地位 64
三、 軟珊瑚(Sinularia flexibilis)的採集和研究方式與生物分類地位 65
第二節、 生物樣本的萃取與分離方式 66
一、 小花蔓澤蘭(Mikania micrantha)分離流程 66
二、 軟珊瑚(Sinularia penghuensis)分離流程 66
三、 軟珊瑚(Sinularia flexibilis)分離流程 66
第三節、 實驗設備儀器及材料 69
一、 實驗設備儀器 69
二、 實驗材料 69
第三章、 化合物結構證明 72
第一節、 軟珊瑚Sinularia flexibilis所分離化合物之結構解析 72
一、 Flexibilone (1)化合物構造解析 72
二、 Sinulariolone (2)化合物構造解析 82
第二節、 軟珊瑚Sinularia penghuensisis所分離化合物之結構 86
一、 (1''E,5''E)-5-(2'',6''-Dimethylocta-1'',5'',7''-trienyl)furan-3-carboxylic acid (3)化合物構造解析 86
第三節、 小花蔓澤蘭Mikania micrantha所分離化合物構造解析 90
一、 Mikanin (4)化合物構造解析 90
二、 Scandenolide (5)化合物構造解析 94
三、 Dihydromikanolide (6)化合物構造解析 97
四、 Mikanolide (7)化合物構造解析 100
五、 Dexoymikanolide (8)化合物構造解析 103
六、 Cylindrinol D (9)化合物構造解析 106
七、 3-hydroxymethyl-6-methoxy-2,3-dihydro-1H-indol-2-ol (10)化合物構造解析 111
第四節、 化合物物理性質及圖譜數據彙整 116
第四章、 生物活性 118
第一節、 生物活性測試之方法 118
一、 人類乳腺癌細胞MDA-MB-231與人類非小細胞肺癌細胞A549細胞毒殺試驗 118
二、 登革熱病毒PL046抑制測試 119
第二節、 生物活性測試之結果 121
一、 人類乳腺癌細胞MDA-MB-231與人類非小細胞肺癌細胞A549細胞毒殺試驗 121
二、 登革熱病毒PL046抑制測試 122
第五章、 結論 123
第六章、 參考資料 125
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