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研究生:傅重瑋
研究生(外文):Chung-Wei Fu
論文名稱:臺灣產海綿Agelas nakamurai及軟珊瑚Cespitularia sp.天然物化學成份與活性之新近研究
論文名稱(外文):The updated Investigation of the Formosan Marine Sponge Agelas nakamurai and Soft Coral Cespitularia sp. chemical constituents and Bioactivity
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:2022
畢業學年度:110
語文別:英文
論文頁數:336
中文關鍵詞:天然產物軟珊瑚海綿細胞毒殺抑菌活性
外文關鍵詞:natural productssoft coralmarine spongecytotoxicityanti-bacteria activity
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本研究探討從臺灣產海綿Agelas nakamurai與軟珊瑚Cespitularia sp.中分離得到的三十個天然產物及其活性研究,由海綿分離得到9-methyladenine-containing diterpenoids (1–6)、taurocyamine sesquiterpenoid (7)、pyridinium derivatives (8–10) 、 bromopyrroles (11–13);另外從軟珊瑚分離得到 verticillene diterpenoids (14–21)、eudesmane-type sesquiterpenoids (22–24)與7-hydroperoxysterols (25–30)。其中有十二個新的天然產物(1–3, 7–9, 11, 14, 22, 與25–27),這些新二次代謝物是藉由光譜方法進行結構的分析鑑定:高解析質譜 (HRESIMS)、核磁共振光譜(NMR) 、紅外光譜(IR)以及紫外光譜(UV)。
在細胞毒殺的活性測試中,化合物3與27對於乳癌細胞(MDA-MB-231)的IC50分別是15.76、15.40 μg/mL,化合物27對於肺癌細胞(A549)也呈現活性(IC50 = 18.74 μg/mL)。除此之外,化合物3對於克雷伯氏肺炎菌與粘質沙雷氏菌呈現顯著的抑菌活性,並且具有抑制枯草桿菌、金黃色葡萄球菌、宋內志賀菌與小腸結腸炎耶爾森氏菌的中等活性。而其他的化合物4、11、23與27對於克雷伯氏肺炎菌也具有中等的抑制活性。
The updated chemical investigation of the secondary metabolites from the Formosan marine sponge Agelas nakamurai and soft coral Cespitularia sp. have obtained thirty natural products 1–30. To be more specific, the compounds from the marine sponge involve 9-methyladenine-containing diterpenoids (1–6), taurocyamine sesquiterpenoid (7), pyridinium derivatives (8–10), and bromopyrroles (11–13);moreover, the secondary metabolites from the soft coral include verticillene diterpenoids (14–21), eudesmane-type sesquiterpenoids (22–24)、7-hydroperoxysterols (25–30), in which there were twelve new compounds (1–3, 7–9, 11, 14, 22, and 25–27). These new chemical structures of metabolites were elucidated via several spectroscopic methods, including High Resolution Electrospray Ionization Mass spectroscopy (HRESIMS), Nuclear Magnetic Resonance spectroscopy (NMR), Infrared spectroscopy (IR), and Ultraviolet–Visible spectroscopy (UV).
In cytotoxic assay, compounds 3 and 27 displayed cytotoxicity to breast cancer cell line (MDA-MB-231) with IC50 = 15.76、15.40 μg/mL. Compound 27 showed cytotoxic activity to lung cancer cell line (A549) with IC50 = 18.74 μg/mL as well. Moreover, antibacterial test for the above compounds revealed compound 3 exhibiting significant activity against Klebsiella pneumoniae and Serratia marcescens with moderate inhibition to Bacillus subtilis, Staphylococcus aureus, Shigella sonnei, and Yersinia enterocolitica. Compounds 4, 11, 23, and 27 also inhibited Klebsiella pneumoniae moderately.
論文審定書 i
誌謝 ii
摘要 iii
Abstract iv
Contents viii
List of Figures xi
List of Tables xxiv
Chapter 1. Introduction 1
Chapter 2. Literature Review 4
Section 2-1. Literature Review of the Genus Agelas 4
Section 2-2. Literature Review of the Genus Cespitularia 45
Chapter 3. Experimental Section 64
Section 3-1. General Experimental Procedures 64
Section 3-2. Organism and Extraction 65
Section 3-3. Biological Activities 74
3.3.1. Cytotoxic Assay 74
3.3.2. Antibacterial Assay 75
Chapter 4. Compound Identification 76
Section 4-1. Compounds from the Marine Sponge Agelas nakamurai 76
4.1.1. Structural Elucidation of Nakamusine A (1) 76
4.1.2. Structural Elucidation of Nakamusine B (2) 87
4.1.3. Structural Elucidation of (+)-Agelasine C (3) 97
4.1.4. Structural Elucidation of 2-Oxoagelasine B (4) 108
4.1.5. Structural Elucidation of (–)-Agelasine D (5) 113
4.1.6. Structural Elucidation of Agelasine F (6) 118
4.1.7. Structural Elucidation of Agelasidine J (7) 123
4.1.8. Structural Elucidation of Agelapyridinium A (8) 133
4.1.9. Structural Elucidation of Pyridinebetaine C (9) 141
4.1.10. Structural Elucidation of Pyridinebetaine B (10) 149
4.1.11. Structural Elucidation of Nakamudine G (11) 153
4.1.12. Structural Elucidation of Laughine (12) 160
4.1.13. Structural Elucidation of Mukanadin C (13) 164
Section 4-2. Compounds from the Soft Coral Cespitularia sp. 168
4.2.1. Structural Elucidation of Cespitulactam M (14) 168
4.2.2. Preparation of Cespitulactam M 6, 2’-diacetate (14a) 179
4.2.3. Structural Elucidation of Cespitulactam D (15) and Cespitulactam F (16) 187
4.2.4. Structural Elucidation of Cespitulin S (17) 194
4.2.5. Structural Elucidation of Cespitularin D (18), Cespitularin O (19), Cespitulactone B (20), and Cespihypotin Q (21) 199
4.2.6. Structural Elucidation of Cespilamide F (22) 212
4.2.7. Structural Elucidation of Atractylenolide II (23) and Atractylenolide III (24) 223
4.2.8. Structural Elucidation of 7β-Hydroperoxygorgosterol (25) 230
4.2.9. Structural Elucidation of 7α-Hydroperoxygorgosterol (26) 243
4.2.10. Structural Elucidation of 7β-Hydroperoxycampesterol (27) 254
4.2.11. Structural Elucidation of 7α-Hydroperoxycampesterol (28) 264
4.2.12. Structural Elucidation of 7β-Hydroperoxycholesterol (29) and 7α-Hydroperoxycholesterol (30) 269
Chapter 5. Bioactivities 276
Section 5-1. Cytotoxic Activity 276
Section 5-2. Antibacterial Activity 277
Chapter 6. Conclusion 279
Chapter 7. Physical Properties and Data Collections 286
References 293
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