鮑氏不動桿菌(Acinetobacter baumannii)為一種伺機性感染的細菌易於發展成抗藥性的菌株，因此容易在醫院內擴散開甚至造成致死率上升。因此，開發新穎的抗生素為日前重要的研究目標之一。另一方面，海洋微生物開發了一系列特殊的有機配位體，為了能幫助海洋微生物收集鐵、鋅與其它微量金屬，其中一些稱為鐵載體（Siderophore）。微量金屬源也被視為抗菌成份或是用以治療患者感染的病菌。
此研究主旨是為了找尋新型的活性化合物，以發展成有效的抗生素，本次研究之樣品為從採樣屏東萬里桐的海綿，經品種鑑定為似雪海綿屬。進行分離純化，從34株細菌及5株真菌中，經由活性篩選得到兩株海洋真菌MR13-TR01及MR13-TA01，分別對實驗室中的九株指標菌進行活性測試，顯示出良好的抗菌活性，特別是鮑氏不動桿菌。另對CAS 培養基做鐵螯合測試也顯示出良好的活性。經由真菌ITS序列鑑定為瑞氏木黴菌(Trichoderma reesei)及深綠木黴菌(Trichoderma atroviride)。經由活性導引，從這兩株真菌的萃取物中得到四個新型的胜肽(peptaibols)類化合物，另外，有十六個已知的化合物被分離出，分別有四個胜肽類化合物、五個聚酮類、兩個雙胺基酸環化衍生物、兩個倍半萜、一個糖醇、一個嘧啶、及一個雙糖類衍生物。上述化合物結構由各種光譜資料﹙紫外光譜、紅外光譜、圆二色谱、核磁共振光譜及質譜﹚和化學方法加以證實。生物活性測試結果顯示，八個胜肽類化合物對鮑氏不動桿菌有良好的抑制活性，特別是化合物1活性最佳，且利用CAS 活性測試顯示出亦有鐵螯合作用之有效性。最特別的是，化合物5 對於口腔癌細胞株CAL 27有良好之活性，其IC50 = 13.0 ug/mL。

Acinetobacter baumannii is an opportunistic pathogen, which easily develop a drug-resistant strain and is liable to spread and increase the mortality in the hospital.Therefore, to develop new antibiotics to treat the patients with infection by A. baumannii became an important research object. On the other hand, marine microorganisms develop a series of specific organic-ligand systems to assist them harvest iron, zinc, and other trace metals to survive in the trace metals-insufficient seawater environments. These organic ligands are species-specific to influence the growth of other microorganisms by scavenging environmental trace metals. Such ligands can be also regarded as anti-microbial components to treat patients infected with pathogens.
To search novel anti-microbial secondary metabolites from marine microorganisms, we found that two marine fungi, Trichoderma reesi (MR13-TR01) and T. atroviride (MR13-TA01), isolated from a sponge Niphates collected from Wan-Li Tong, Pingtung County, showed clearly good inhibitory effects against eight bacterial indicators and one fungal indicator, especially for A. baumannii. Both also showed the iron-chelating effect by the Chrome azurol S (CAS) assay. Through the bioactivity-guided fractionation isolation (BGFI), we isolated four new peptaibols, as well as 16 known compounds, including four peptaibols, five polyketides, two known diketopiperazines, two sesquiterpenes, one alitol, one nucleoside, and one disaccharide, from the extracts of the two marine fungi. The structures of the compounds mentioned above were elucidated by spectroscopic (UV, IR, CD, NMR, HRESI-MS) and chemical methods. In addition, eight peptaibols showed inhibitory effect against A. baumannii, especially for compound 1. And some of them also had the clear iron-chelating effect by the CAS assay. In addition to the compound 5 had a great activity for the oral cancer cell CAL 27, and the IC50 = 13.0 ug/mL。

中文摘要 i
Abstract ii
目錄 iv
圖目錄 vii
表目錄 viii
Trichoderma atroviride 和Trichoderma reesi 所分離得到之化合物 x
第一章 緒論 1
第一節 前言 1
第二節 木黴菌屬型態分布及應用 2
第三節 木黴菌屬研究背景 3
第四節 木黴菌屬之成分研究及文獻回顧 4
一、 抗菌活性 5
二、Peptaibols之溶血性效果10 9
三、細胞膜穿透 10
第五節Trichoderma spp.其他類型之化合物 12
第二章 材料方法與分離流程 24
第一節 木黴菌屬Trichoderma spp.鑑定 24
第二節 抗菌活性篩選之指標菌 24
第三節、鮑氏不動桿菌 26
第四節 木黴菌屬(Trichoderma spp.)成分之萃取及實驗方法 27
一、分離流程 27
二、Peptaibols之酸水解及Chiral HPLC 之分析73 31
三、Peptaibols之Marfey’s method分析74, 75, 76 32
第三章 結構解析 33
第一節 Peptaibols之解析 33
第二節Paracelsin B (1) 之結構證明 35
第三節Trichocellins A-IX (2*)之結構證明 46
第四節Trichocellin C-I (3*)之結構證明 56
第五節Trichocellins C-I I (4*)之結構證明 65
第六節 Trichocellins C-III(5*)之結構證明 74
第七節Paracelsin E (6)之結構證明 83
第八節 Trichocellins A-V (7)結構證明 92
第九節Trichocellins A-IV(8) 之結構證明 101
第十節Trichodermanone C (9)之結構證明 114
第十一節 Trichodermanone B(10)之結構證明 119
第十二節 Trichodermanone A (11)之結構證明 124
第十三節Sorbicillinol (12)之結構證明 129
第十四節 6-n-pentyl-α-pyrone (13)之結構證明 134
第十五節 10(Z)-cyclonerotriol (14)之結構證明 138
第十六節 10(E)-cyclonerotriol(15)之結構證明 143
第十七節 cyclo(D-Tyr-D-Pro) (16) 之結構證明 148
第十八節 Cyclo-Ala-Pro (17)之結構證明 153
第十九節Mannitol (18)之結構證明 158
第二十節Adenosine (19)之結構證明 161
第二十一節1, 3, 4, 6-Tetra-O-acetyl-β-D-fructofuranosyl) 2, 3, 4, 6-tetra -O-acetyl-α-D-glucopyranoside (20) 之結構證明 166
第四章 最佳生長環境及活性測試 170
第五章 Trichoderma spp.之代謝物比對 172
第六章 生物活性測試 179
第一節 Punch-plate Assay Method 179
第二節 抗菌活性測試 MIC 181
第三節 CAS agar diffusion assay 90 182
第四節 細胞毒殺 183
第七章 結論 186
第八章 實驗材料與方法 187
第二節 儀器設備與試藥 190
第三節 海洋共生菌純化與分離 193
第四節 化合物物理性質與光譜數據整理 195
第九章 參考文獻 207

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