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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 李宗徽(Tzong-Huei Lee) | |
| dc.contributor.author | Yuen-Sing Lee | en |
| dc.contributor.author | 李元新 | zh_TW |
| dc.date.accessioned | 2023-03-19T23:22:40Z | - |
| dc.date.copyright | 2022-07-05 | |
| dc.date.issued | 2022 | |
| dc.date.submitted | 2022-06-06 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/85730 | - |
| dc.description.abstract | 本研究利用病原菌與病毒篩選活性平台 (Staphylococcus aureus, Candida albicans, Cryptococcus neoformans, Escherichia coli和Epstein-Barr virus) 來篩選具有抗菌和抗病毒潛力的海葵衍生真菌株。 實驗結果顯示，由瘤砂海葵 (Palythoa sp.) 單離出之衍生真菌株Arthrinium arundinis MA30之粗萃物具有抗 S. aureus、C. albicans 與EBV病毒的顯著效果，因而選定該菌株進行其天然物研究。接著，利用OSMAC (one strain many compound) 的方式進行了不同條件下的液態和糙米固態培養後，分離並純化此株真菌的次級代謝物，計獲得 32個化合物，再藉由各種光譜資料解析其結構，其中 6個為新化合物，分別為 arthrinoic acid (1)、hexylaconitic anhydride methyl ester (2)、iso-hydroxylated hexylitaconic acid (3) 、(3S,8R)-8-hydroxy-3-carboxy-2-methylenenonanoic acid (4)、arthripenoid G (5) 及arthripenoid H (6)，另外 26 個為已知化合物，分別為succinic acid (7)、sumiki's acid (8)、pyromucic acid (9)、4-(2-hydroxyethyl)benzoic acid (10)、4-hydroxyphenylacetic acid (11)、2-hydroxyphenylacetic acid (12)、methyl vanillate (13)、6,8-dihydroxy-3,4-dimethylisochromen-1-one (14)、3,4,8-THT (15)、2β-methyl-5-hydroxy-2H-1-benzopyran-4(3H)-one (16)、2β-methyl-4-methoxy-3,4-dihydro-2H-1-benzopyran-5-ol (17)、(+)-mellein (18)、(R)-2-hexyl-3-methylenesuccinic acid (19)、palmitic acid (20)、linoleic acid (21)、thalictric acid (22)、2-hexyl-3-methylmaleic anhydride (23)、TXIB (24)、anomalin A (25)、anomalin B (26)、1,3,5,6-tetrahydroxy-8-methylxanthone (27)、ergosterol (28)、cytochalasin E (29)、arthripenoid B (30)、arthripenoid C (31) 和arthripenoid F (32)。所有純物質在抗發炎活性平台的評估上，得知化合物5、6、27、30、31和32具有抑制小鼠神經膠細胞BV-2產生一氧化氮的 (nitric oxide, NO) 效果，於10 µM下抑制NO產生的比例介於80至100%之間，其中化合物27和31有不錯的活性且不具顯著的細胞毒性，與IC50分別為5.3 ± 0.6 和1.55 ± 0.4 μM。 | zh_TW |
| dc.description.abstract | In an attempt to investigate bioactive fungal strains, preliminary field-sampling and bio-assays were conducted. The microorganisms used in antimicrobial and antiviral bio-assay platform included Staphylococcus aureus, Cryptococcus neoformans, Candida albicans, and Escherichia coli, as well as Epstein-Barr virus (EBV), respectively. From the macroalgae and sea anemone collected at northeastern coast of Taiwan (Badouzi), 220 fungal strains were isolated. Among these, Arthrinium arundinis MA30 from sea anemone was selected due to its significant inhibition against S. aureus, C. neoformans, and EBV. An OSMAC (one strain many compounds) strategy was applied, where Arthrinium arundinis MA30 was cultured in different environments, including liquid-state fermentation under shaking, liquid-state fermentation under aeration, and solid-state fermentation. As a result of isolation and purification on the fermented products, 32 compounds were identified and six of which were previously unreported compounds, including arthrinoic acid (1), hexylaconitic anhydride methyl ester (2), iso-hydroxylated hexylitaconic acid (3), (3S,8R)-8-hydroxy-3-carboxy-2-methylenenonanoic acid (4), arthripenoid G (5), and arthripenoid H (6), in addition of 26 known compounds, including succinic acid (7), sumiki's acid (8), pyromucic acid (9), 4-(2-hydroxyethyl)benzoic acid (10), 4-hydroxyphenylacetic acid (11), 2-hydroxyphenylacetic acid (12), methyl vanillate (13), 6,8-dihydroxy-3,4-dimethylisochromen-1-one (14), 3,4,8-THT (15), 2β-methyl-5-hydroxy-2H-1-benzopyran-4(3H)-one (16), 2β-methyl-4-methoxy-3,4-dihydro-2H-1-benzopyran-5-ol (17), (+)-mellein (18), (R)-2-hexyl-3-methylenesuccinic acid (19)，palmitic acid (20), linoleic acid (21), thalictric acid (22), 2-hexyl-3-methylmaleic anhydride (23), TXIB (24), anomalin A (25), anomalin B (26), 1,3,5,6-tetrahydroxy-8-methylxanthone (27), ergosterol (28), cytochalasin E (29), arthripenoid B (30), arthripenoid C (31), and arthripenoid F (32). The structures of these compounds were elucidated by comprehensive spectroscopic methods, and some of their absolute configurations were determined by Mosher’s reagent, circular dichroism, and single crystal X-ray diffraction. Of these compounds, 5, 6, 27, 30, 31, and 32 exhibited high inhibition rate towards nitric oxide (NO) production in mouse glial cells BV-2 cells, and the proportion of inhibiting NO production at 10 µM ranging from 80 to 100%. The IC50 values of the most active compounds 27 and 31 were 5.3 ± 0.6 and 1.55 ± 0.4 μM, respectively, without significant cytotoxicity. | en |
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| dc.description.tableofcontents | 口試委員會審定書..........................................................i 致謝....................................................................ii 中文摘要................................................................iii ABSTRACT.................................................................v TABLE OF CONTENTS.......................................................xi LIST OF FIGURES.........................................................xv LIST OF TABLES.......................................................xxiii LIST OF ABBREVIATIONS..................................................xix 1. INTRODUCTION AND RESEARCH PURPOSE.....................................1 1.1 Marine-derived fungi and their medicinal properties..................1 1.2 Introduction of fungal strain........................................5 2. LITERATURE REVIEW.....................................................5 3. RESULTS..............................................................22 3.1 Fermentation........................................................22 3.1.1 Liquid-state fermentation under aeration..........................22 3.1.2 Liquid-state flask fermentation under shaking.....................24 3.1.3 Solid-state fermentation..........................................26 3.2 Structure elucidation of previously unreported compounds............28 3.2.1 Structure elucidation of compound 1...............................28 3.2.2 Structure elucidation of compound 2...............................35 3.2.3 Structure elucidation of compound 3...............................44 3.2.4 Structure elucidation of compound 4...............................52 3.2.5 Structure elucidation of compound 5...............................61 3.2.6 Structure elucidation of compound 6...............................73 3.3 Structure elucidation of previously reported compounds..............84 3.3.1 Structure elucidation of compound 7...............................84 3.3.2 Structure elucidation of compound 8...............................86 3.3.3 Structure elucidation of compound 9...............................89 3.3.4 Structure elucidation of compound 10..............................91 3.3.5 Structure elucidation of compound 11..............................94 3.3.6 Structure elucidation of compound 12..............................96 3.3.7 Structure elucidation of compound 13..............................99 3.3.8 Structure elucidation of compound 14.............................102 3.3.9 Structure elucidation of compound 15.............................105 3.3.10 Structure elucidation of compound 16............................108 3.3.11 Structure elucidation of compound 17............................111 3.3.12 Structure elucidation of compound 18............................114 3.3.13 Structure elucidation of compound 19............................117 3.3.14 Structure elucidation of compound 20............................120 3.3.15 Structure elucidation of compound 21............................122 3.3.16 Structure elucidation of compound 22............................125 3.3.17 Structure elucidation of compound 23............................127 3.3.18 Structure elucidation of compound 24............................131 3.3.19 Structure elucidation of compound 25............................135 3.3.20 Structure elucidation of compound 26............................139 3.3.21 Structure elucidation of compound 27............................143 3.3.22 Structure elucidation of compound 28............................147 3.3.23 Structure elucidation of compound 29............................151 3.3.24 Structure elucidation of compound 30............................157 3.3.25 Structure elucidation of compound 31............................161 3.3.26 Structure elucidation of compound 32............................166 3.4 Physical properties of each compound...............................170 3.5 Bioactivity of compounds...........................................176 4. EXPERIMENT SECTIONS.................................................178 4.1 Instruments and reagents...........................................178 4.1.1 Physical properties measuring instruments........................178 4.1.2 Column chromatography colloids...................................179 4.1.3 Reagents and solvents............................................179 4.1.4 Fungal culture media.............................................179 4.1.5 Bacterial culture media..........................................179 4.2 Materials and methods..............................................180 4.2.1 Research samples.................................................180 4.2.2 Isolation and screening of fungal strain.........................180 4.2.3 Bioassay platforms...............................................182 4.2.4 Bioassay experimental procedure..................................183 4.2.5 Fungal strain for biological screening...........................183 4.2.6 Bacterial strains for biological screening.......................184 4.2.7 Identification of fungal strain..................................184 4.3 Fungus culture and its chemical constituents.......................187 4.3.1 Preparation of medium............................................187 4.3.2 Preservation of fungal strains...................................187 4.3.3 Flask shake liquid-state fermentation extraction.................187 4.3.4 Chemical constituent purification and isolation of fungus from flask shake liquid-state fermentation........................................188 4.3.5 Chemical constituent purification and isolation of fungus from liquid-state fermentation under aeration...............................192 4.3.6 Chemical constituent purification and isolation of fungus from solid-state fermentation...............................................196 4.4 Assessment of anti-inflammatory activity...........................197 4.4.1 Cell culture.....................................................197 4.4.2 Griess reagent assay.............................................198 4.4.3 Cytotoxicity test................................................199 4.4.4 Purpose and principle of MTT assay...............................199 4.4.5 MTT assay........................................................200 5. DISCUSSIONS.........................................................201 6. REFERENCES..........................................................204 7. APPENDIX............................................................216 | |
| dc.language.iso | en | |
| dc.subject | Arthrinium arundinis | zh_TW |
| dc.subject | 天然物 | zh_TW |
| dc.subject | 抗發炎 | zh_TW |
| dc.subject | 細胞毒性 | zh_TW |
| dc.subject | arthripenoid | zh_TW |
| dc.subject | 瘤砂海葵衍生真菌 | zh_TW |
| dc.subject | arthripenoid | en |
| dc.subject | anti-inflammation | en |
| dc.subject | natural products | en |
| dc.subject | cytotoxicity | en |
| dc.subject | Arthrinium arundinis | en |
| dc.subject | Palythoa sp. derived fungi | en |
| dc.title | 瘤砂海葵衍生真菌株Arthrinium arundinis MA30之成分研究 | zh_TW |
| dc.title | Chemical Constituents from Palythoa sp. derived Arthrinium arundinis MA30 | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 110-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 蕭哲志(George Hsiao),陳日榮(Jih-Jung Chen),宋秉鈞(Ping-Jyun Sung) | |
| dc.subject.keyword | 瘤砂海葵衍生真菌,Arthrinium arundinis,arthripenoid,天然物,抗發炎,細胞毒性, | zh_TW |
| dc.subject.keyword | Palythoa sp. derived fungi,Arthrinium arundinis,arthripenoid,natural products,anti-inflammation,cytotoxicity, | en |
| dc.relation.page | 224 | |
| dc.identifier.doi | 10.6342/NTU202200789 | |
| dc.rights.note | 同意授權(全球公開) | |
| dc.date.accepted | 2022-06-06 | |
| dc.contributor.author-college | 生命科學院 | zh_TW |
| dc.contributor.author-dept | 漁業科學研究所 | zh_TW |
| dc.date.embargo-lift | 2022-07-05 | - |
| 顯示於系所單位： | 漁業科學研究所 | |
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