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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 周宏農 | |
| dc.contributor.author | Tian-Jiun Yu | en |
| dc.contributor.author | 余天峻 | zh_TW |
| dc.date.accessioned | 2021-06-16T10:26:29Z | - |
| dc.date.available | 2015-08-20 | |
| dc.date.copyright | 2013-08-20 | |
| dc.date.issued | 2013 | |
| dc.date.submitted | 2013-08-15 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/60697 | - |
| dc.description.abstract | 銅綠微囊藻 (Microcystis aeruginosa) 是被研究很廣泛的藻種，實驗室中的藻株M.TY-1主要的用途為生產微囊藻毒，而其提純之剩餘物質並未被研究。.由過去研究可知，微囊藻除了會產生微囊藻毒外，還會產生許多種類的活性天然物，這些天然物常具有蛋白酶的抑制活性，在過去研究中發現其可能與微囊藻的自我保護機制或是做為他感物質的應用有關，而本研究也期待能自微囊藻中夠發現更多活性天然物，以利後續之研究。
本實驗中共純化出五個可能具有活性的化合物，分別為兩個micropeptin類：Micropeptin TY1046 (1)、Micropeptin TY1042 (2) 與三個monogalactosyl monoacylglycerols (MGMGs)：1-O-(4,7,10,13-hexadecatetraenoyl)-3-O-β-D-galactopyranosylglycerol (3)、1-O-(6,9,12-octadecatrienoyl)-3-O-β-D-galactopyranosylglycerol (4)、1-O-(7,10-hexadecadienoyl)-3-O-β-D-galactopyranosylglycerol (5)，其中化合物1、2、4為新的化合物。由前人文獻推測micropeptin TY1046與TY1042可能具有chymotrypsin之抑制活性，而從NMR之氫譜顯示，micropeptins很可能存在一分子內氫鍵的作用力。 三個MGMGs則具有iNOS之抑制活性，其IC50分別為42.16 μM、39.24 μM與27.85 μM，而由實驗結果推論，其iNOS之抑制活性會隨其長鏈上不飽和度的減少而變強。 | zh_TW |
| dc.description.abstract | The freshwater cyanobacterium Microcystis aeruginosa has been extensively studied. The use of strain M•TY-1in our laboratory is to produce MC-LR. However, the fractions without MC-LR was not studied. It is known that Microcystis aeruginosa produces many classes of natural products. Several hypotheses on the function of these compounds in the physiology and ecology of cyanobacteria have been discussed, mostly related either to grazing protection or to allelopathy. Here we investigated the chemical
components of M•TY-1 for their structures and possible activities. Two micropeptins and three monogalactosyl monoacylglycerols (MGMGs) was isolated and structure determinated on the basis of spectroscopic analysis. They are Micropeptin TY1046 (1), Micropeptin TY1042 (2), 1-O-(4,7,10,13-hexadecatetraenoyl)-3-O-β-D-galactopyranosylglycerol (3), 1-O-(6,9,12-octadecatrienoyl)-3-O-β-D-galactopyranosylglycerol (4) and 1-O-(7,10-hexadecadienoyl)-3-O-β-D-galactopyranosylglycerol (5). Compound (1) and (2) may exhibit the inhibitory of chymotrypsin. In addition, the proton NMR data of compound (1) in DMSO indicated an intermolecular hydrogen bond within the ring structure of micropeptins. compound (3), (4) and (5) are iNOS inhibitors. Their IC50 are 42.16 μM, 39.24 μM, and 27.85 μM， Decreasing unsaturation of the fatty acid side chain enhances the NO inhibitory activity. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-16T10:26:29Z (GMT). No. of bitstreams: 1 ntu-102-R99b45007-1.pdf: 8419208 bytes, checksum: 7c20473344d93bfe0aaf90dadf12e21e (MD5) Previous issue date: 2013 | en |
| dc.description.tableofcontents | 中文摘要‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥I
英文摘要‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥II 總目錄‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥III 表目錄‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥V 圖目錄‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥VI 壹、前言‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥1 貳、文獻回顧‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥3 2.1 Microcystins‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥4 2.2 Aerucyclamides‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥5 2.3 Aeruginosins‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥6 2.4 Cyanopeptolins‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥7 2.5 Anabaenopeptins‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥11 2.6 Kawaguchipeptins ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥12 2.7 Microginins‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥13 參、材料與方法 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥14 3.1 藥品及儀器 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥14 3.2 樣品來源 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥14 3.3 化合物的純化 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥14 肆、結果與討論 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥16 4.1 化合物之結構解析 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥16 4.1.1 化合物1之結構解析‥‥‥‥‥‥‥‥‥‥‥‥16 4.1.2 化合物2之結構解析‥‥‥‥‥‥‥‥‥‥‥‥25 4.1.3化合物3之結構解析 ‥‥‥‥‥‥‥‥‥‥‥‥34 4.1.4化合物4之結構解析 ‥‥‥‥‥‥‥‥‥‥‥‥40 4.1.5化合物5之結構解析 ‥‥‥‥‥‥‥‥‥‥‥‥46 4.2 化合物之活性探討 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥52 4.2.1 化合物1與2之活性探討 ‥‥‥‥‥‥‥‥‥‥52 4.2.2 化合物1與2之分子內作用力探討 ‥‥‥‥‥‥55 4.2.3 化合物3, 4, 5之活性探討‥‥‥‥‥‥‥‥‥54 伍、參考文獻 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥56 表目錄 表1、Micropeptins之組成胺基酸與其抑制活性‥‥‥‥‥‥‥‥‥‥‥‥‥‥10 表2、Micropeptin TY1046之1D、2D NMR訊號‥‥‥‥‥‥‥‥‥‥‥‥‥20 表3、Micropeptin TY1042之1D、2D NMR訊號‥‥‥‥‥‥‥‥‥‥‥‥‥29 表4、化合物3之1D、2DNMR訊號‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥36 表5、化合物4之1D、2DNMR訊號‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥42 表6、化合物5之1D、2DNMR訊號‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥48 表7、化合物3, 4, 5之NO抑制活性‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥48 圖1、Microcystin之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥4 圖2、Aerucyclamide A、B、C與D之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥5 圖3、Aeruginosin 98A、101、103A與298A之結構‥‥‥‥‥‥‥‥‥‥‥‥‥6 圖4、Cyanopeptolin 1020與Cyanopeptolin 963A之結構‥‥‥‥‥‥‥‥‥‥‥7 圖5、Micropeptin SD944、979、999與1002之結構‥‥‥‥‥‥‥‥‥‥‥‥7 圖6、Glutamate與Ahp間的轉換‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥ 8 圖7、micropeptins的基本結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥9 圖8、Anabaenopeptin A之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥11 圖9、Ferintoic acid A與B之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥11 圖10、Kawaguchipeptin A 與B之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥12 圖11、Microginin之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥13 圖12、Microginin 299A、299B與SD755之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥13 圖13、化合物1至5之純化流程‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥15 圖14、Micropeptin TY1046之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥16 圖15、Micropeptin TY1046之COSY與HMBC相關‥‥‥‥‥‥‥‥‥‥‥‥19 圖16、Micropeptin TY1046之紅外光譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥21 圖17、Micropeptin TY1046之ESI-MS圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥21 圖18、Micropeptin TY1046之800 MHz氫譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥22 圖19、Micropeptin TY1046之800 MHz碳譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥22 圖20、Micropeptin TY1046之800 MHz HSQC圖譜‥‥‥‥‥‥‥‥‥‥‥‥23 圖21、Micropeptin TY1046之800 MHz COSY圖譜‥‥‥‥‥‥‥‥‥‥‥‥23 圖22、Micropeptin TY1046之800 MHz HMBC圖譜‥‥‥‥‥‥‥‥‥‥‥‥24 圖23、Micropeptin TY1046之800 MHz NOESY圖譜‥‥‥‥‥‥‥‥‥‥‥24 圖24、Micropeptin TY1042之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥25 圖25、Micropeptin TY1042之COSY與HMBC相關‥‥‥‥‥‥‥‥‥‥‥‥28 圖26、Micropeptin TY1042之紅外光譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥30 圖27、Micropeptin TY1042之ESI-MS圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥30 圖28、Micropeptin TY1042之800 MHz氫譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥31 圖29、Micropeptin TY1042之800 MHz碳譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥31 圖30、Micropeptin TY1042之800 MHz HSQC圖譜‥‥‥‥‥‥‥‥‥‥‥‥32 圖31、Micropeptin TY1042之800 MHz COSY圖譜‥‥‥‥‥‥‥‥‥‥‥‥32 圖32、Micropeptin TY1042之800 MHz HMBC圖譜‥‥‥‥‥‥‥‥‥‥‥‥33 圖33、Micropeptin TY1042之800 MHz NOESY圖譜‥‥‥‥‥‥‥‥‥‥‥‥33 圖34、1-O-(4,7,10,13-hexadecatetraenoyl)-3-O-β-D -galactopyranosylglycerol之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥34 圖35、化合物3之COSY與HMBC相關‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥35 圖36、化合物3之紅外光譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥36 圖37、化合物3之ESI-MS圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥37 圖38、化合物3之800 MHz氫譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥37 圖39、化合物3之800 MHz碳譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥37 圖40、化合物3之800 MHz HSQC圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥38 圖41、化合物3之800 MHz COSY圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥38 圖42、化合物3之800 MHz HMBC圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥39 圖43、化合物3之800 MHz NOESY圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥39 圖44、1-O-(6,9,12-octadecatrienoyl)-3-O-β-D -galactopyranosylglycerol之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥40 圖45、化合物4之COSY與HMBC相關‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥41 圖46、化合物4之紅外光譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥42 圖47、化合物4之ESI-MS圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥43 圖48、化合物4之500 MHz氫譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥43 圖49、化合物4之500 MHz碳譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥43 圖50、化合物4之500 MHz HSQC圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥44 圖51、化合物4之500 MHz COSY圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥44 圖52、化合物4之500 MHz HMBC圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥45 圖53、化合物4之500 MHz NOESY圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥45 圖54、1-O-(7,10-hexadecadienoyl)-3-O-β-D -galactopyranosylglycerol之結構‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥46 圖55、化合物5之COSY與HMBC相關‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥47 圖56、化合物5之紅外光譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥48 圖57、化合物5之ESI-MS圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥49 圖58、化合物5之500 MHz氫譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥49 圖59、化合物5之500 MHz碳譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥49 圖60、化合物5之500 MHz HSQC圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥50 圖61、化合物5之500 MHz COSY圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥50 圖62、化合物5之500 MHz HMBC圖譜‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥51 圖63、化合物5之500 MHz NOESY圖譜 ‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥51 圖64、化合物1之1H-NMR 圖譜 (MeOH-d4)‥‥‥‥‥‥‥‥‥‥‥‥‥‥53 圖65、化合物1之1H-NMR 圖譜 (DMSO-d6)‥‥‥‥‥‥‥‥‥‥‥‥‥‥53 圖66、化合物2之1H-NMR 圖譜 (MeOH-d4)‥‥‥‥‥‥‥‥‥‥‥‥‥‥53 圖67、化合物2 之分子內氫鍵示意圖‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥‥54 | |
| dc.language.iso | zh-TW | |
| dc.subject | 天然物 | zh_TW |
| dc.subject | 銅綠微囊藻 | zh_TW |
| dc.subject | Microcystis aeruginosa | en |
| dc.subject | natural products | en |
| dc.title | 銅綠微囊藻M.TY-1之天然物研究 | zh_TW |
| dc.title | Natural Products from Microcystis aeruginosa strain M.TY-1 | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 101-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 沈雅敬,李宗徽,盧重光,陳逸民 | |
| dc.subject.keyword | 銅綠微囊藻,天然物, | zh_TW |
| dc.subject.keyword | Microcystis aeruginosa,natural products, | en |
| dc.relation.page | 63 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2013-08-15 | |
| dc.contributor.author-college | 生命科學院 | zh_TW |
| dc.contributor.author-dept | 漁業科學研究所 | zh_TW |
| 顯示於系所單位： | 漁業科學研究所 | |
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