對於藥物的開發及發展而言，海洋生物被視為是一個很好的天然物資源，如從海鞘中取得trabectedin (抗癌藥)，從海洋放線菌 (Marinispora sp.) 取得 marinisporolide A1 (抗菌藥) 等。我們從屏東的萬里桐採集到四隻海洋共生菌 (自Cerviconia sp.獲得C-01，自Palythoa tuberculosa獲得C-03及C-07和自Npphates sp. 獲得C-05) 其16S rRNA基因序列的分析結果近似產微球菌 (Microbulbifer variabilis)。我們利用HPLC-PDA-MS和質譜分子網絡綜合比較此四株菌在其二次代謝物的相關性及活性物質的區間，發現其對仙人掌桿菌有不同的活性區間。另一方面，我們藉由色層分析方法進一步的探討C-03的生物活性物質組成，目前我們從其乙酸乙酯萃取液中分離到11個二酮哌嗪類化合物1-11，6個核苷酸類 12-17，1個吡咯烷類化合物18，1個吡啶甲酰胺19，苯甲酸烷類化合物20和1個吩嗪類化合物21。其中化合物8為新的化合物。 另一方面，我們也探討了海洋真菌，海洋炭層菌 (Nemania maritima) 為炭層菌屬 (Nemania) 真菌中的一員。此真菌從紅樹林的枯木上分離純化而得。N. maritima 經由固態培養 (PDA agar) 並使用乙酸乙酯萃取該真菌。透過傳統層析與高效液能層析儀等技術分離純化，共得四個已知化合物，包括化合物 22-25。所有化合物結構皆由各種光譜資料 (紫外光光譜、紅外光光譜、核磁共振光譜和質譜儀等) 加以證明確定。
進一步將此上述分離化合物進行抗菌、抗病毒等活性測試，化合物21則對於抗金黃色葡萄球菌 (Staphyloccocus aureus) 和仙人掌桿菌 (Bacillus cereus) 有明顯的活性效果，其MIC皆為8 μg/mL。而在抗病毒方面：化合物21具有抑制C型肝炎 (hepatitis C virus)的效果，其SI值為4.06。在抗登革熱病毒 (dengue virus)方面：化合物5、6、10、12和13也有明顯的抑制效果其SI值分別為5.89、7.41、8.92、13.33和8.19。另外，雖然化合物22-25在過去文獻中也沒有相關的抗病毒活性報導，且在抗菌和抗C型肝炎病毒方面沒有明顯的活性抑制效果，但在抗登革熱病毒活性測試方面，我們發現化合物24和25有明顯的活性效果且，其SI (CC50/EC50 ) 值分別為4.67及9.52。

Marine organisms are regarded as an immense resource of diverse natural products for drug discovery and development, such as trabectedin from tunicate, marinisporolide A1 form Marinispora sp. and so on. In our lab, we got symbiotic marine bacteria C-01 from Cerviconia sp, C-03 and C-07 from Palythoa sp., and C-05 from Npphates sp., respectively, in Wan-Li Tong, Pingtung County. Based on 16S rRNA gene sequencing analysis, they all were identified as Microbulbifer variabilis We compared with four Microbulbifer strains by HPLC-PDA-MS fractionations and the mass spectral molecular networking to explore relationship of secondary metabolites. We further explored the bioactive components from the C-03 by chromatographic methods. Till now, one new diketopiperazine 8, as well as ten 1~7, and 9~11, six nucleotides 12~17, one pyridine 18 one pyrrolidine 19, one benzoic acid 20 and, one phenazine 21, have been isolated from the ethyl acetate extract of M. variabilis C-03. We also explored marine fungus with Nemania maritima, belonging to genus Nemania. This fungus was isolated from the mangrove dead wood. We cultured N. maritima with PDA agar, and extracted the fungus with ethyl acetate. The extracts were subjected to traditional silica column chromatography and high performance liquid chromatography to give four compounds, including adenosine (22) barceloneic acid A (23), barceloneic acid B (24) and ergosterol peroxide (25). All the chemical structures were characterized by spectroscopic methods (UV, IR, NMR, and ESI-MS).
We test three kind of bioactive test about anti-bacterial, anti-virus (hepatitis C virus and dengue virus). Compound 21 showed significant anti-microbial activity against to Staphyloccocus aureus and Bacillus cereus with the same minimum inhibitory concentration (MIC) value of 8 μg/mL. In addition, the antiviral test revealed that against hepatitis C virus with SI (CC50/EC50) value of 21 was 4.06. The SI values of 5, 6, 10, 12 and 13 against dengue virus were 5.89、7.41、8.92、13.33, and 8.19, respectively. In addition, the compounds of 24 and 25 did not find the relevant reports in past literature about anti-virus activity. Anti-bacterial and anti-virus (hepatitis C virus) have not significant inhibitory effect, but we find compound of 24 and 25 exerted inhibitory effect against dengue virus’s with SI (CC50/EC50) values of 4.67 and 9.52, respectively.

目錄
論文審定書 i
謝誌 ii
中文摘要 iii
Abstract v
目錄 vii
圖目錄 xxi
表目錄 xxi
第一章 緒論 1
第一節 前言 1
第二節 產微球莖菌屬型態分布及應用 3
第三節 產微球莖菌屬研究背景 4
第四節 產微球莖菌屬之成分研究與文獻整理 8
一、 抗菌作用 13
二、 細胞毒殺作用 15
第五節 炭層菌屬之成分研究與文獻整理 16
第二章 材料方法與分離流程 27
第一節 產微球莖菌屬Microbulbifer variabilis親緣關係圖 27
第二節 實驗用抗菌活性篩選用微生物指標菌 29
第三節 產微球莖菌Microbulbifer variabilis成份之萃取與分離流程 32
第四節 海洋真菌Nemania maritima 40
第五節 海洋炭層菌成份之萃取與分離流程 41
第六節 質譜分子網絡 (Mass Spectral Molecular Networking) 50
第七節 海洋細菌菌株之萃取物的製備 51
第三章 化合物之結構解析 52
第一節 Cyclo-(glycine-L-proline) (1)之結構證明 52
第二節 Cyclo-(glycine-L-leucine) (2)之結構證明 58
第三節 Cyclo-(glycine-L-phenylalanine) (3)之結構證明 64
第四節 Cyclo-(glycine-D-tyrosine) (4)之結構證明 70
第五節 Cyclo-(L-proline-L-leucine) (5)之結構證明 76
第六節 Cyclo-(4-trans-hydroxy-L-proline-L-leucine) (6)之結構證明 81
第七節 Cyclo-(4-trans-hydroxy-D-proline-L-leucine) (7)之結構證明 86
第八節 Cyclo-(4,6-trans-hydroxy-proline-D-leucine) (8)之結構證明 92
第九節 Cyclo-(L-proline-L-tyrosine) (9)之結構證明 99
第十節 Cyclo-(4-trans-hydroxy-L-proline-L-phenylalanine) (10)之結構證明 105
第十一節 Cyclo-(4-trans-hydroxy-L-proline-L-tyrosine) (11)之結構證明 110
Diketopiperazines (DPK) 文獻碳氫及旋光值 116
第十二節 Uracil (12)之結構證明 126
第十三節 5-Methyluracil (13)之結構證明 131
第十四節 2'-Deoxyuridine (14)之結構證明 136
第十五節 Thymidine (15)之結構證明 141
第十六節 Uridine (16)之結構證明 147
第十七節 2'-Deoxyadenosine (17)之結構證明 152
第十八節 4-Hydroxy-2-pyrrolidinone (18)之結構證明 157
第十九節 Pyridine-3-carboxamide (19)之結構證明 163
第二十節 p-Hydroxybenzaldehyde (20)之結構證明 168
第二十一節 Griseoluteic acid (21)之結構證明 172
第二十二節 Adenosine (22)之結構證明 180
第二十三節 Barceloneic acid A (23)之結構證明 186
第二十四節 Barceloneic acid B (24)之結構證明 193
第二十五節 Ergosterol peroxide (25)之結構證明 200
第四章 M. variabilis (C-03) 最佳生長條件及生物活性測試 204
第五章 M. variabilis 四菌株活性及其代謝物比較 205
第一節 四菌株活性比較 205
第二節 活性化合物生物活性測試 209
第三節 質譜分子網絡 (Mass Spectral Molecular Networking) 211
第四節 M. variabilis (C-03) 二次代謝物的滯留時間 218
第六章 生物活性測試 228
第一節 抗C型肝炎病毒活性 228
第二節 抗登革熱病毒活性 231
第三節 抗菌活性測試MIC 234
第七章 結論 235
第八章 實驗相關部分 237
第一節 海洋微生物培養基 237
第二節 儀器設備與試藥 240
第三節 海洋共生菌純化與分離 242
(1) 海洋細菌M. variabilis實驗流程圖 242
(2) 樣品採樣 243
(3) 細菌分離實驗流程圖 244
(4) 細菌純化實驗流程圖 245
(5) 保存菌株實驗流程圖 245
(6) 需鹽性測試 246
(7) 生物活性測試方法 247
第四節 各化合物物理性質與光譜數據整理 248
第九章 參考文獻 260

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