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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 周宏農(Hong-Nong Chou) | |
| dc.contributor.author | Jui-Che Chen | en |
| dc.contributor.author | 陳睿哲 | zh_TW |
| dc.date.accessioned | 2021-06-13T02:19:24Z | - |
| dc.date.available | 2007-02-01 | |
| dc.date.copyright | 2007-02-01 | |
| dc.date.issued | 2007 | |
| dc.date.submitted | 2007-01-30 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/30882 | - |
| dc.description.abstract | 在生物活性篩檢的實驗中，得知棲狀褐茸藻Hincksia mitchellae(Harvey) Silva之粗萃物具有抗病毒及抗凝血的活性，其中最明顯的藻褐素成分，具有抑制前列腺癌及髓性白血病進入細胞凋亡的活性，也因此期待能從棲狀褐茸藻的培養中得到更多的活性化合物。本研究自二氯甲烷層分離出5個化合物，分別為fucoxanthin (1)、apo-9’-fucoxanthinone (2)、grasshopper ketone (3)、apo-13’-fucoxanthinone (4)、apo-13’-fucoxanthinol (5)，自正己烷層分離出7個化合物，分別為trans-phytol (6)、linoleic acid (7)、 phytyl lenoleate (8)、phytyl 9-octadecenoate (9)、phytyl hexadecanoate (10)、α-tocopheryl quinine (11)、fucosterol (12)，以及自正丁醇層分離出3個化合物，分別為adenosine (13)、 tryptophane (14)、uridine (15)，其中化合物5為新的化合物。本研究為第一篇相關棲狀褐茸藻天然物的研究報告，這些源自棲狀褐茸藻的的藻褐素及其代謝物，在文獻上曾有抗腫瘤的活性，phytyl ester類化合物具有抗潰瘍的活性，α-tocopheryl quinone具有抑制白血癌細胞株P-388及直腸癌細胞株HT-29的活性，而fucosterol對於P-388有抑制作用，但在本研究中
並未測試相關活性。 | zh_TW |
| dc.description.abstract | Crude extracts of Hincksia mitchellae (Harvey) Silva has been found to exhibit significant anticlotting activity and antiviral activity in our previous screening task. The major pigment in the extract, fucoxanthin was reported to exhibit anticancer activity against human prostate and leukemia cancer. Here we investigated the chemical constituents of H. mitchellae for their structures and possible activities. Components of fucoxanthin (1), and its derivatives, apo-9’-fucoxanthinone (2), grasshopper ketone (3), apo-13’-fucoxanthinone (4), apo-13’-fucoxanthinol (5), and trans-phytol (6), linoleic acid (7), phytyl acylesters, phytyl lenoleate (8), phytyl 9-octadecenoate (9), phytyl hexadecanoate (10), α-tocopherylquinone (11), fucosterol (12), adenosine (13), tryptophane (14), and uridine (15) were isolated and structure determined on the basis of spectroscopic analysis and their correlation with the published spectroscopic data. Among them, compound (5) was a new compound ever published in the papers. This is the first paper of natural products from Hincksia mitchellae. Some of the isolated components are known to be bioactive, such as fucoxanthin and its derivatives in anticarcinoma activities, phytyl esters in antiulcer activity, α-tocopherylquinone in cytotoxicity against P-388 and HT-29 cell and
fucosterol in cytotoxicity against P-388. However, none of the isolated components was tested for their bioactivities. | en |
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| dc.description.tableofcontents | 總 目 錄
中文摘要…………………………………………………………………I 英文摘要………………………………………………………………...II 總目錄…………………………………………………………….…….III 圖目錄…………………………………………………………………..VI 表目錄…………………………………………………………………..IX 壹、 前言………………………………………………………………..1 貳、 褐藻Hincksia mitchellae之內含物研究…………………………8 2.1 海藻材料簡介……………………………………………….8 2.2 褐藻Hincksia mitchellae量化培養………………………..10 2.3 褐藻Hincksia mitchellae之天然物的分離………………..11 2.4 褐藻Hincksia mitchellae之天然物結構解析……………..13 2.4.1 Fucoxanthin之結構解析……………………...……13 2.4.2 apo-9’-fucoxanthinone之結構解析…………..……17 2.4.3 Grasshopper ketone之結構解析………………...….20 2.4.4 apo-13’-fucoxanthinone之結構解析………….....…23 2.4.5 apo-13’-fucoxanthinol之結構解析………………...26 2.4.6 trans-phytol之結構解析……………………..….….32 2.4.7 Linoleic acid之結構解析……………………..........35 2.4.8 Phytyl linoleate之結構解析…………………...…...38 2.4.9 Phytyl 9-octadecenoate及phytyl hexadecanoate結構解析………………………………………………………....42 2.4.10 α-tocopherylquinone之結構解析…………………46 2.4.11 Fucosterol之結構解析……………………………49 2.4.12 Adenosine之結構解析……………………………52 2.4.13 Uridine之結構解析……………………………….55 2.4.14 Tryptophane之結構解析………………………….58 参、討論與結論…………………………………………………….….62 肆、實驗部分………………………………………………………..….65 4.1 本實驗所使用之儀器及藥品…………………………..…...65 4.2 褐藻Hincksia mitchellae之萃取及分離流程………………66 4.3 褐藻Hincksia mitchellae之天然物純化流程………………67 4.3.1 Fucoxanthin之純化流程……………………...……68 4.3.2 apo-9’-fucoxanthinone之純化流程…………..……70 4.3.3 Grasshopper ketone之純化流程………………...….72 4.3.4 apo-13’-fucoxanthinone之純化流程………….....…74 4.3.5 apo-13’-fucoxanthinol之純化流程………………...76 4.3.6 trans-phytol之純化流程……………………..….….78 4.3.7 Linoleic acid之純化流程……………………..........80 4.3.8 Phytyl linoleate之純化流程…………………...…...82 4.3.9 Phytyl 9-octadecenoate及phytyl hexadecanoate純化流程………………………………………………………....84 4.3.10 α-tocopherylquinone之純化流程…………………86 4.3.11 Fucosterol之純化流程……………………………88 4.3.12 Adenosine之純化流程……………………………90 4.3.13 Uridine之純化流程……………………………….92 4.3.14 Tryptophane之純化流程………………………….94 伍、參考文獻………………………………………………………………………………………96 圖 目 錄 圖1各天然物之純化流程……………………………………………...12 圖2 化合物1之紅外線光譜…………………………………………...14 圖3 化合物1之氫譜…………………………………………………...15 圖4 化合物1之碳譜…………………………………………………...15 圖5 化合物1之COSY圖譜…………………………………………...16 圖6 化合物1之HMBC圖譜………………………………………….16 圖7 化合物2之紅外光譜…………………………………………….18 圖8 化合物2之氫譜……………………………………………….…19 圖9 化合物2之碳譜………………………………………………….19 圖10 化合物3之紅外光譜……………………………………………21 圖11 化合物3之氫譜……………………………………………….…21 圖12 化合物3之碳譜………………………………………………….22 圖13 化合物4之紅外光譜……………………………………………24 圖14 化合物4之氫譜……………………………………………….…25 圖15 化合物4之碳譜………………………………………………….25 圖16 二組COSY片段…………………………………………………27 圖17 HMBC所得到之片段1………………………..…………………27 圖18 HMBC所得到之片段2………………………………………..…28 圖19 以NOESY建立相對立體結構…………………………………28 圖20 化合物5之紅外光譜……………………………………………29 圖21 化合物5之氫譜………………………………………………….29 圖22 化合物5之碳譜………………………………………………….30 圖23 化合物5之COSY圖譜………………………………………….30 圖24 化合物5之HMBC圖譜…………………………………………31 圖25 化合物5之NOESY圖譜………………………………………31 圖26 化合物6之紅外光譜……………………………………………33 圖27 化合物6之氫譜……………………………………………….…33 圖28 化合物6之碳譜………………………………………………….34 圖29 化合物7之紅外光譜…………………………………………….36 圖30 化合物7之氫譜……………………...…………………………..36 圖31 化合物7之碳譜…………………………...……………………..37 圖32 化合物8之紅外光譜…………………………………………….39 圖33 化合物8之氫譜………………………………………………….40 圖34 化合物8之碳譜………………………………………...………..40 圖35 化合物8反應後GC-MS分析圖譜……………..………………41 圖36 分液9之氫譜……………………………………………….…...43 圖37 分液9之碳譜…………………………………………………….44 圖38 分液9之HMBC譜………………………………………………44 圖39 分液9反應後GC-MS分析圖譜…………………………….…45 圖40 化合物11之紅外光譜………………………………………….47 圖41 化合物11之氫譜………………………………………………..48 圖42 化合物11之碳譜………………………………………………..48 圖43 化合物12之紅外光譜………………………………………….50 圖44 化合物12之氫譜………………………………………………..50 圖45 化合物12之碳譜………………………………………………..51 圖46 化合物12之質譜………………………………………………...51 圖47 化合物13之紅外光譜…………………………………………..53 圖48 化合物13之氫譜………………………………………………...53 圖49 化合物13之碳譜………………………………………….……54 圖50 化合物13之COSY圖譜…………………………………..……54 圖51 化合物14之紅外光譜………………………………………..…56 圖52 化合物14之氫譜……………………………………………..…56 圖53 化合物14之碳譜………………………………………….…….57 圖54 化合物15之紅外光譜…………………………………..………59 圖55 化合物15之氫譜…………………….……………………….…59 圖56 化合物15之碳譜……………………………………………….60 圖57 化合物15之COSY圖譜………………………………………60 圖58 化合物15之HMBC圖譜………………………………………61 表 目 錄 表一 Modified SWM-Ⅲ培養基之組成……………………………….10 表二 Fucoxanthin 之1H-, 13C-NMR數據與COSY及HMBC關連......69 表三 apo-9’-fucoxanthinone之NMR數據與COSY及HMBC關連...71 表四 Grasshopper ketone之NMR數據與COSY及HMBC關連.........73 表五 apo-13’-fucoxanthinoneNMR數據與COSY及HMBC關連......75 表六 apo-13’-fucoxanthinol之NMR數據與COSY及HMBC關連….77 表七 trans-phytol之1H-, 13C-NMR數據與COSY及HMBC關連…...79 表八 Linoleic acid之NMR數據與COSY及HMBC關連…………....81 表九 Phytyl linoleate之NMR數據與COSY及HMBC關連…………83 表十 分液9之1H-, 13C-NMR數據與COSY及HMBC關連……….....85 表十一 α-tocopherylquinone 之NMR數據與COSY及HMBC關連................................................................................................87 表十二 Fucosterol 之1H-, 13C-NMR數據與COSY及HMBC關連….89 表十三 Adenosine 之1H-, 13C-NMR數據與COSY及HMBC關連....91 表十四 Uridine 之1H-, 13C-NMR數據與COSY及HMBC關連……93 表十五 Tryptophane 之1H-, 13C-NMR數據與COSY及HMBC關連.95 | |
| dc.language.iso | zh-TW | |
| dc.title | 棲狀褐茸藻Hincksia mitchellae(Harvey) P. C. Silva
天然物提純與結構解析 | zh_TW |
| dc.title | Isolation and Structure Elucidation of Natural Products
from Hincksia mitchellae(Harvey) P. C. Silva | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 95-1 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 沈雅敬(Ya-Ching Shen),盧重光(Chung-Kuang Lu),李宗徽(Tzong-Huei Lee) | |
| dc.subject.keyword | 天然物,褐藻,藻褐素, | zh_TW |
| dc.subject.keyword | natural products,brown algae,fucoxanthin, | en |
| dc.relation.page | 107 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2007-01-31 | |
| 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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