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研究生:方暉喻
研究生(外文):Hui-Yu Fang
論文名稱:台灣軟珊瑚Scleronephthya gracillimum、紅藻Laurencia brongniartii與褐藻Homoeostrichus formosana所含二次代謝物及生物活性之研究
論文名稱(外文):Studies on the Secondary Metabolites and Biological Activities from the Formosan Soft Coral Scleronephthya gracillimum, Red Alga Laurencia brongniartii and Brown Alga Homoeostrichus formosana
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:博士
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:2014
畢業學年度:102
語文別:英文
論文頁數:519
中文關鍵詞:美麗骨穗軟珊瑚紅羽凹頂藻台灣多扇藻彈性蛋白酶超氧自由基
外文關鍵詞:superoxide anionHomoeostrichus formosanaLaurencia brongniartiiScleronephthya gracillimumelastase release
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為了尋找新穎的生物活性化合物,我們針對美麗骨穗軟珊瑚,紅羽凹頂藻及台灣多扇藻二次代謝物來進行調查。從美麗骨穗軟珊瑚的有機萃取物分離出十四個新的pregnane類的化合物 1、4、5、7−15、16、17 和一個新雙萜類化合物3-methyl-5-(10′-acetoxy-2′,6′,10′- trimethylundecyl)-2-penten-5-olide 18,包括三個已知化合物 2、3、6。除此,從紅羽凹頂藻的丙酮萃取物分離出一個新穎的多溴吲哚類化合物 20 和十一個已知的代謝物 19, 21−30。更進一步,從台灣多扇藻首次分離出一個新穎meroditerpenoid相關天然產物 31,一個半合成是經由乙醯化的衍生物 36 和四個已知化合物 32−35。代謝物所分離到的結構經由多方面光譜分析方法,特別是一維和二維核磁共振實驗。固醇類糖苷9−12糖基部分的絕對構型經由o-tolylthiocarbamate衍生物水解和高效液相層析儀分析來決定。再者化合物2的絕對立體構型,則經由Mosher’s 方法之酯化反應來證明。化合物1−4、9−11、15−17、19−25、27−32和34−36顯示對特定的癌細胞株具有細胞毒殺活性。而化合物1、4、8、14、16–19、25和28–30因酯多醣體刺激RAW264.7巨噬細胞的iNOS蛋白質被抑制而發現在體外具有抗發炎活性。化合物1、4、8、13、14、16–18、28和29也能有效減少COX-2蛋白質。然而,化合物19顯示抑制產氣腸桿菌(ATCC13048),腸炎沙門氏菌(ATCC13076) 和黏質沙雷氏菌(ATCC25419)抗菌活性以及化合物28 和29 抑制黏質沙雷氏菌的活性。
值得注意化合物32 顯示對於人類嗜中性白血球超氧自由基的產生以及彈性蛋白酶顯著的抑制活性。化合物35 顯示對於超氧自由基的產生以及彈性蛋白酶中等的抑制活性,然而,化合物36 發現對於兩者具有微弱抑制效果。有趣的,化合物31 顯示具有輕微的促進超氧自由基的產生以及彈性蛋白酶釋放情形。根據初步對於化合物31–36抑制仙人掌桿菌,金黃色葡萄球菌,沙門氏鼠傷寒桿菌,綠膿桿菌,腸炎沙門氏菌和小腸結腸耶氏菌的分析。化合物31顯示抑制所有六種病原體以及化合物32, 35和36有顯著的抑制綠膿桿菌的活性。
In order to search for new bioactive compounds, we have investigated the secondary metabolites of the soft coral Scleronephthya gracillimum, the red alga Laurencia brongniartii and the brown alga Homoeostrichus formosana. Chemical constituents from the organic extracts of S. gracillimum, fourteen new pregnane-type steroids 1, 4, 5, 7−15, 16, 17, and a new diterpenoid 3-methyl-5-(10′-acetoxy-2′,6′,10′- trimethylundecyl)-2- penten-5-olide 18, including three known pregnane-type steroids 2, 3, 6 have been isolated. In addition, a novel polybrominated indole derivative 20 and eleven known metabolites 19, 21−30 were isolated from the acetone extracts of L. brongniartii. Furthermore, one novel meroditerpenoid-related natural product 31, one semi-synthesis through acetylated derivative of 31 (compound 36), along with four known compounds 32−35 were isolated for the first time from Homoeostrichus formosana. The structures of the isolated metabolites were elucidated through extensive spectroscopic methods, in particular 1D and 2D NMR experiments. The absolute configurations of sugar moieties in steroidal glycosides 9−12 were determined by HPLC analysis of the o-tolylthiocarbamate derivatives of the liberated sugars hydrolysed from these steroidal glycosides. Moreover, the absolute configurations of 2 were established by application of the modified Mosher’s method. Compounds 1−4, 9−11, 15−17, 19−25, 27−32 and 34−36 have been exhibited cytotoxicity toward a limited panel of cancer cell lines. Compounds 1, 4, 8, 14, 16–19, 25 and 28–30 were found to display significant in vitro anti-inflammatory activity in LPS-stimulated RAW 264.7 macrophage cells by inhibiting the expression of the iNOS protein. Compounds 1, 4, 8, 13, 14, 16–18, 28, and 29 also could effectively reduce the level of the COX-2 protein. Moreover, 19 were exhibited antibacterial activity against Enterobacter aerogenes (ATCC13048), Salmonella enteritidis (ATCC13076), and Serratia marcescens (ATCC25419), and compounds 28 and 29 showed activity against Serratia marcescens. Compound 32 has been exhibited remarkable inhibitory effects on superoxide anion generation and elastase release by human neutrophils. Compound 35 showed moderately inhibitory effects on superoxide anion generation and the elastase release by human neutrophils. Interestingly, compound 31 was exhibited mild activity to enhance human neutrophils superoxide anion generation and elastase release. According to the initial analysis of compounds 31–36 were assayed for antibacterial acticity against Bacillus cereus (ATCC14579), Staphylococcus aureus (ATCC9144), Salmonella typhimurium (ATCC14028), Pseudomonas aeruginosa (ATCC 27853), Serratia marcescens (ATCC25419) and Yersinia enterocolitica (ATCC23715), 31 exhibited against all six pathogens and compounds 32, 35 and 36 significantly inhibit the activity of P. aeruginosa.
論文審定書
摘 要 i
ABSTRACT iii
Contents ix
List of Figures xii
List of Tables xxiv

Chapter 1 Introduction 1
Chapter 2 Literature Review 4
Chapter 3 Experimental Section 175
Section I General Experimental Procedures 175
Section II Organism and Extraction 177
Section III Cytotoxicity Assay 189
Section IV Anti-inflammatory Assay 190
Section V Antibacterial Assay 192
Chapter 4 Results and Discussion 193
Elucidation of Sclerosteroid A (1) 193
Elucidation of Stereonsteroid A (2) 193
Elucidation of Ceratosteroid C (3) 193
Elucidation of Sclerosteroid B (4) 206
Elucidation of Sclerosteroid C (5) 214
Elucidation of Pregna-1,20-dien-3-one (6) 214
Elucidation of Sclerosteroid D (7) 224
Elucidation of Sclerosteroid E (8) 232
Elucidation of Sclerosteroid F (9) 240
Elucidation of Sclerosteroid G (10) 250
Elucidation of Sclerosteroid H (11) 259
Elucidation of Sclerosteroid I (12) 268
Elucidation of Sclerosteroid J (13) 277
Elucidation of Sclerosteroid K (14) 287
Elucidation of Sclerosteroid L (15) 295
Elucidation of Sclerosteroid M (16) 303
Elucidation of Sclerosteroid N (17) 313
Elucidation of 3-Methyl-5-(10′-acetoxy-2′,6′,10′-trimethylundecyl)-
2-penten-5-olide (18) 322
Elucidation of 3-Methylthio-2,4,6-tribromoindole (19) 330
Elucidation of 2-Methylsulfinyl-4,5,6-tribromoindole (20) 336
Elucidation of Convolutamydine A (21) 343
Elucidation of 3-Methylsulfinyl-2,4,6-tribromoindole (22) 345
Elucidation of Itomanindole B (23) 345
Elucidation of Itomanindole A (24) 345
Elucidation of 4,6-Dibromo-2,3-(dimethylthio)indole (25) 345
Elucidation of 4,6-Dibromo-2,3-di(methylsulfinyl)indole (26) 345
Elucidation of 2-Methylsulfinyl-3-methylthio-4,5,6-tri-bromoindole (27) 353
Elucidation of 2,3-Di(methylthio)-4,5,6-tribromoindole (28) 353
Elucidation of 3-Methylthio-2,4,5,6-tetrabromoindole (29) 353
Elucidation of 3,3-Bis(4,6-dibromo-2-methylthio) indole (30) 358
Elucidation of 2-(4′,8′-Dimethylnona-3′,7′-dienyl)-8-hydroxy- 2,6-dimethyl-2H-chromene (31) and 2-(4′,8′-Dimethylnona- 3′,7′-dienyl)-2,6-dimethyl- 2H-chromene-8-acetate (36) 360
Elucidation of Methylfarnesylquinone (32) 374
Elucidation of Isololiolide (33) 377
Elucidation of 71-Hydroxy-pheophorbide-a-methyl ester (34) 380
Elucidation of β-carotene (35) 383
Chapter 5 Bioactivities 385
Section I: Cytotoxicity Assay 386
Section II: Anti-inflammatory assay for 1–4, 6–14 and 16–30 387
Section III: Anti-inflammatory assay for 31, 32, 35 and 36 389
Section IV: Antibacterial Assay 391
Chapter 6 Reactions 399
Chapter 7 Conclusion 406
Chapter 8 Physical Properties and Data collections 409
References 413
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