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博碩士論文 etd-1102113-100601 詳細資訊
Title page for etd-1102113-100601
論文名稱
Title
粉葉馬尾藻之化學成分研究
Study on the Chemical Constituents of the Brown Alga Sargassum glaucescens
系所名稱
Department
畢業學年期
Year, semester
語文別
Language
學位類別
Degree
頁數
Number of pages
186
研究生
Author
指導教授
Advisor
召集委員
Convenor
口試委員
Advisory Committee
口試日期
Date of Exam
2013-08-27
繳交日期
Date of Submission
2013-12-02
關鍵字
Keywords
不飽和脂肪酸、二次代謝物、細胞保護、粉葉馬尾藻、單萜類化合物
monoterpenoid, Sagrassum glaucescens, cytoprotective, secondary metabolites, unsaturated fat
統計
Statistics
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The thesis/dissertation has been browsed 5685 times, has been downloaded 202 times.
中文摘要
粉葉馬尾藻廣泛分布在熱帶及溫帶的潮間帶,在台灣,粉葉馬尾藻具有龐大的生物量。藉由文獻搜尋得知這一屬的褐藻中,具有一類良好抗氧化的化合物-褐藻多酚,在本次的研究中,藉由研究粉葉馬尾藻的化學成分,發展具有抗氧化能力的分子,作為未來醫藥或保健食品上的應用。
本研究自粉葉馬尾藻乙酸乙酯層經由管柱層析及高效能液相層析儀中分離得到二十二個化合物,包含固醇類化合物fucosterol (1)、 24-hydroperoxy-24-vinylcholesterol (2),醣醇類化合物mannitol (3),單萜類化合物sargapenes A (4)及B (5)及 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]bis(propane-1-chloro-2-diol) (6)與其代謝物3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]-(propane-1-broml, 1’-chloro-2,2’-diol), 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]-(propane-1-iodo, 1’-chloro-2,2’-diol), 1,3-bis[1-chloro-3-(4-(2-phenylpropan-2-yl)phenoxy)propan-2-ol]glycerol (7-9),kjellmanianone (10)及三個不飽合脂肪酸長鏈,eicosapentaenoic acid (11)、α-linolenic acid (12)、eicosatetraenoic acid (13),藻褐素代謝物,apo-9'-fucoxanthinone (14)、apo-13'-fucoxanthinone (15),兩個脫鎂葉綠素類化合物phaeophytin a (16)、132-Hydroxy-(132-S)-phaeophytin a (17),長鏈烯烴化合物1-octacosene (18)、(6Z,9Z,12Z,15Z)-henicosa-1,6,9,12,15-pentaene (19)、(3Z, 6Z,9Z,12Z,15Z)-henicosa-3,6,9,12,15,20-hexaene (20)及,兩個長鏈的化合物,arachidonic acid α-monoglyceride (21) 2-(3-eicosatetraenoyloxy-2-hydroxypropanoxy) methylpropenoic acid (22),上述化合物利用核磁共振儀及質譜等工具,進行結構解析,並對化合物1, 4, 5, 6, 10, 14,進行細胞保護活性測試,並發現其中化合物4, 5, 6, 14具有細胞保護的活性。
Abstract
The brown algae Sargassum glaucescens is widely in temperate, tropical, and subtropical waters in both intertidal and subtidal zones, which showed large biomass in Taiwan. In the study, we would like to investigate the chemical constituents of S. glaucescens to develop its anti-oxidant reagents for future medicine application.
We investigated on the EtOH layer of S. glaucescens, which was futher sparated by column chromatography and high performance liquid chromatography and give twenty two compounds, including two steroids: fucosterol (1) and 24-hydroperoxy-24-vinylcholesterol (2), mannitol (3), two monoterpenoids: sargapenes A (4) and B (5) and 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]bis(propane-1-chloro-2-diol) (6), 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]-(propane-1-broml, 1’-chloro-2,2’-diol), 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]-(propane-1-iodo,1’-chloro-2,2’-diol), 1,3-bis[1-chloro-3-(4-(2-phenylpropan-2-yl)phenoxy)propan-2-ol]glycerol (7-9), kjellmanianone (10), three unsaturated fatty acid, eicosapentaenoic acid (11), α-linolenic acid (12) and eicosatetraenoic acid (13), two fucoxanthine metabolites, apo-9'-fucoxanthinone (14), apo-13'-fucoxanthinone (15), two chlorophyll metabolites phaeophytin a (16), 132-Hydroxy-(13-S)-phaeophytin a (17), three polyunsaturated olefins, (6Z,9Z,12Z,15Z)-henicosa-1,6,9,12,15-pentaene (19), (3Z,6Z,9Z,12Z,15Z)-henicosa-3,6,9,12,15,20-hexaene (20),
three fulvellic acid type compounds arachidonic acid α-monoglyceride (21), 2-(3-eicosatetraenoyloxy-2-hydroxypropanoxy), Their structures were determined by spectroscopic methods. And we taked compounds 1, 4, 5, 6, 10, and 14 to cell cytoprotective activity test. We found compounds 4, 5, 6 and 14 with the active of cytoprotective activity test.
目次 Table of Contents
目次
中文摘要…………………………………………………………i
英文摘要…………………………………………………………ii
圖次………………………………………………………………vii
表次………………………………………………………………xi
第一章
第一節 前言..……………………………………………………1
第二節 植物型態..………………………………………………3
第三節 馬尾藻屬文獻回顧……………………………………4
第一項 化學成分整理…………..………………………………5.
第二項 活性相關研究回顧整理..………………………………15
第四節 研究目的......……………………………………………19
第二章 研究材料與分離純化方法………………………………20
第三章 化合物之結構證明
第一節 Fucosterol (1)之結構證明……………………………25
第二節 24-Hydroperoxy-24-vinylcholesterol (2)之結構證明 ……31
第三節 Mannitol (3)之結構證明…...…………………………………36
第四節 Sargapene A (4)之結構證明……………………………………39
第五節 Sargapene B (5)之結構證明……………………………………45
第六節 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]bis-
(propane-1-chloro-2-diol) (6)之結構證明…………………52
第七節 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]-
(propane-1-broml,1’-chloro-2,2’-diol) (7)之結構證……….58
第八節 3,3’-[Propane-2,2-diylbis(benzene-4,1-diyloxy)]-
(propane-1-iodo, 1’-chloro-2,2’-diol) (8)之結構證明……64
第九節 3,3-Bis[1-chloro-3-(4-(2-phenylpropan-2-yl)phenoxy)-
propan-2-ol]glycerol (9)之結構證明………………………70
第十節 Kjellmanianone (10)之結構證明……………76
第十一節 Eicosapentaenoic acid (11)之結構證明……80
第十二節 α-Linolenic acid (12)之結構證明……………85
第十三節 Eicosatetraenoic acid (13)之結構證明……89
第十四節 Apo-9'-fucoxanthinone (14)之結構證明……93
第十五節 Apo-13'-fucoxanthinone (15)之結構證明……99
第十六節 Phaeophytin a (16)之結構證明…………105
第十七節 13 2 -Hydroxy-(13 2 -S)-phaeophytin a (17)之結構證明………113
第十八節 1-Octacosene (18)之結構證明………………………………… 118
第十九節 (6Z,9Z,12Z,15Z)-Henicosa-1,6,9,12,15-pentaene (19)
之結構證明……………………………………122
第二十節 (3Z,6Z,9Z,12Z,15Z)-Henicosa-3,6,9,12,15,20-hexaene (20)
之結構證明……………………………………………122
第二十一節 Arachidonic acid α-monoglyceride (21)之結構證明…………126
第二十二節 2-Eicosatetraenoyloxy-2-hydroxypropanoxy)-
methylpropenoic acid (22)之結構證明 ………………131
第四章 藥理活性實驗
第一節 細胞保護實驗方式………………………………………………136.
第二節 細胞保護篩選結果………………………………………………138
第五章 結論 ……………………………………………………………142
第六章 相關實驗部分
第一節 植物材料與分離流程……………………………………………143
第二節 儀器、試藥與溶劑……………………………………………147
第三節 化合物光譜整理………………………………………………….149
第七章 參考文獻…………………………………………………167
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