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研究生:謝珮文
研究生(外文):Pei-Wen Hsieh
論文名稱:石竹科植物菁芳草、瞿麥、長萼瞿麥化學成分及Dianthramide類生物鹼化合物之合成與其生物活性之研究
論文名稱(外文):Studies on The Chemical Constituents of Drymaria diandra, Dianthus superbus, and Dianthus superbus var. logicalycinus, and the Synthetic` Dianthramide Alkaloid Analogues, and Their Biological Activities
指導教授:吳永昌
指導教授(外文):Yang-Chang Wu
學位類別:博士
校院名稱:高雄醫學大學
系所名稱:藥學研究所博士班
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2005
畢業學年度:93
語文別:中文
論文頁數:230
中文關鍵詞:菁芳草生物活性瞿麥長萼瞿麥Dianthramide類生物鹼
外文關鍵詞:Drymaria diandraDianthramide AlkaloidbioactivityDianthus superbus var. logicalycinusDianthus superbus
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本論文主要希望建立台灣產石竹科植物(Formosan Caryophyllaceous Plants)所含cyclic peptide類化合物之分離純化、結構解析及其相關生物活性如抗血小板凝集、抗腫瘤與抗發炎等方法及資料的建立。採集了菁芳草(Drymaria diandra Bl.)、及長萼瞿麥(Dianthus superbus var. longicalycinus Will)之地上部,與由中藥行所購得之中藥瞿麥(Dianthus superbus L.)分別進行化學成分分離及純化與生物活性關係的探討。共得到四十個化合物,包括:2個alkaloids:drymaritin (DR-15)與2’-methoxydianthramide B (DS-A12)、5個flavonoids:diandraflavone (DR-31)、torosaflavone A (DR-26)、isovitexin (DR-30)、isofurcatain (DR-32)與7-methoxy isofurcatain (DR-33),9個cyclic peptides: diandrine A (DR-23)、diandrine B (DR-22)、diandrine C (DR-28)、diandrine D (DR-29)、dianthin C (DS-P6)、dianthin D (DS-P3)、dianthin E (DS-P4)、dianthin F (DS-P5)與longicalycinin A (DS-P7),2個steroids:spinasterol (DR-21)與spinasterol-β-D-glycoside(DR-27),5個triterpene saponins:dianthoside A (DS-T1)、dianthoside B (DS-T2)、dianthoside G (DS-T7)、dianthoside H (DS-T8)與vaccaroside A (DS-T22),2個norsesquiterpenes:3-oxo-α-ionol (DR-11)與megastigma-4,7-diene-3,9-dione (DR-12),以及15個其他類化合物:anemonin (DR-9)、hexadecanoic acid (DR-10)、methyl 5-hydroxy-4-oxopentanoate (DR-13)、glycerol-α-lignocerate (DR-14)、p-hydroxybenzoic acid (DR-16)、p-hydroxybenaldehyde (DR-17)、vallinic acid (DR-18)、isovanillin (DR-19)、4-methoxy-benzoic aicd methyl ester (DR-20)、cis-p-coumarate (DR-24)、3,4-dihydroxybenzoic acid (DR-25)、aurantiamide benzoate (DS-O10)、4-(2-hydroxy-ethyl)-2-methoxy-phenol (DS-O11)、vanillin (DS-O12)、3-(4-hydroxy-3-methoxy-phenyl)-propionic acid methyl ester (DS-O13)。上述化合物皆利用光譜分析和配合衍生物之製備,加以證明及確認其結構式,其中包含十二個新化合物,以及二十三個首次自該等植物分離得到之化合物。經活性篩選後發現化合物DR-23顯示出對collagen (Col) 所引起的凝集反應有選擇性的抑制作用,其IC50值為44.2 µM。而DR-31具有對人類嗜中性白血球(neutrophils) superoxide generation 抑制活性,其IC50值為10.0 µg/ ml。此外DR-9具有anti-HIV活性,其EC50為2.80 µM,TI值為20.6。
除上述天然物之化學與生物活性研究外,為探討Dianthus屬所含dianthramide alkaloids及其類似物之化學結構與生物活性相關性,共合成七十一個化合物。這些合成的化合物分別進行了細胞毒殺、抗血小板凝集、抗發炎(包括人類嗜中性白血球超氧自由基、elastase釋放及ICAM-1附著因子抑制作用)、以及抗人類冠狀病毒等活性篩選測試。並從這些活性篩選中建立了dianthramide alkaloids及其類似物之活性與化學結構的相關性(structure-activities relationship)。其中化合物DS-14、DS-R15、DS-16、DS-R21、DS-R31、及DS-R41正進行其抗血小板凝集、ICAM-1附著因子抑制作用與人類嗜中性白血球超氧自由基與elastase釋放抑制作用等活性之藥理機轉研究。
The aim of this dissertation is building up the data including the isolation, structural elucidation, and bioactivities, eg. antiplatelet aggregation, anti-inflammatory, and cytotoxicities of cyclic peptides from three Formosan Caryophyllaceous plants, Drymaria diandra, Dianthus superbus, and Dianthus superbus var. longicalycinus. Fourty compounds were isolated including two alkaloids, drymaritin (DR-15) and 2’-methoxydianthramide B (DS-A12); five flavonoids, torosaflavone A (DR-26), diandraflavone (DR-31), isovitexin (DR-30), isofurcatain (DR-32), and 7-methoxyisofurcatain (DR-33); nine cyclic peptides, diandrine A~ D (DR-22、23、28、29), dianthin C-F (DS-P3~6), and longicalycinin A (DS-P7); two steroids, spinasterol (DR-21) and spinasterol-β-D-glycoside (DR-27); five triterpenoid saponins, dianthoside A, B, G, H (DS-T1, 2, 7, 8), and vaccaroside A (DS-T22); two norsesquiterpenes, 3-oxo-α-ionol (DR-11) and megastigma-4,7-diene-3,9-dione (DR-12), and the other fifteen misllenous compounds, anemonin (DR-9), hexadecanoic acid (DR-10), methyl 5-hydroxy-4-oxopentanoate (DR-13), glycerol-α-lignocerate (DR-14), p-hydroxybenzoic acid (DR-16), p-hydroxybenaldehyde (DR-17), vallinic acid (DR-18), isovanillin (DR-19), 4-methoxy-benzoic aicd methyl ester (DR-20), cis-p-coumarate (DR-24), 3,4-dihydroxybenzoic acid (DR-25), aurantiamide benzoate (DS-O10), 4-(2-hydroxy-ethyl)-2-methoxy-phenol (DS-O11), vanillin (DS-O12), and 3-(4-hydroxy-3-methoxy-phenyl)-propionic acid methyl ester (DS-O13). The structures of them were elucidated and established on the basis of spectoscopic data and chemical derivates. Among them, twelve compounds are new, and twenty-three ones were firstly derived from these plants. Additionally, compound DR-23 exhibited highly slective inhibitory effect on the platelet aggregation induced by collagen; compound DR-31 showed inhibitory activity to neutrophil superoxide generation stimulated by fMLP. Furthermore, drymaritin exhibited anti-HIV effect with an EC50 value of 2.80 µM and a TI value of 20.6
The dianthramide alkaloids and their analogues, which were isolated from the genus Dianthus, were selected as the targets for the further medicinal chemistry study. Seventy-one compounds were synthesized and screened for their cytotoxicity, antiplatelet activity, antiinflammatory, inhibition of neutrophil elastase release, ICAM-1 expression inhibition, and anti-HCoVs activities. On the basis of these screenings, the SARs of these compounds were established or proposed. The mechanisms of the most potent compounds, DS-R14, DS-R15, DS-R16, DS-R21, DS-R31, and DS-R41 are underinvestiged for the pharmacological mechanism to anti-platelet aggregation, inhibition of neutrophil elastase release, and ICAM-1 expression inhibition, respectively.
目 錄
目錄………………………………………………………………………………… I
圖表目錄…………………………………………………………………………… III
誌謝…..…………………………………………………………………………… XV
中文摘要…………………………………………………………………………… 1
英文摘要…………………………………………………………………………… 3
第一篇 石竹科植物菁芳草、瞿麥、及長萼瞿麥化學成分與生物活性之研究...5
第一章 緒論……………………………………………………………………….. 5
第一節 研究背景與動機……………………………………………………... 5
第二節 植物型態特性與分佈………………………………………………... 9
第三節 過去研究文獻與整理 …………………………………………….. 11
第四節 高等植物所含Cyclic Peptide之研究 ………………………….. 25
第二章 植物成分之抽取與分離…………………………………………………..47
第三章 化合物之結構證明及生物活性…………………………………………. 71
第一節 Diandrine A (DR-23) 之結構證明…….…………………….…….. 71
第二節 Diandrine B (DR-22) 之結構證明…….……………………….….. 79
第三節 Diandrine C (DR-28) 之結構證明…….……………………….….. 87
第四節Diandrine D (DR-29) 之結構證明….….…………….…………….. 94
第五節Dianthin C (DS-P6) 之結構證明……….………….……………....102
第六節Dianthin D (DS-P3) 之結構證明..…….…………………..……… 110
第七節Dianthin E (DS-P4) 之結構證明….….…………………………….116
第八節Dianthin F (DS-P5) 之結構證明………….……………………….124
第九節Longicalycinin A (DS-P7) 之結構證明…………………………... 128
第十節2’-Methoxydianthramide B (DS-A12) 之結構證明………………134
第十一節Drymaritin (DR-15) 之結構證明………………..………….…...137
第十二節Diandraflavone (DR-31) 之結構證明…………..………….….. 144
第十三節 天然物之生物活性…………………………………….………... 149
第二篇 Dianthramide類生物鹼化合物之合成與生物活性之研究……..….... 154
第一章 緒論….……………………………………………….…………….…… 154
第一節 前言…………………………………………….…………….…….. 154
第二節 合成方法………………….…………………….………………..... 155
第二章 生物活性之研究結果與討論….………………….…………….……… 197
第一節 生物活性實驗方法………………………….……………………... 197
第二節 生物活性篩檢結果與討論….….………….………………………. 198
第三篇 結論…………………………………...……….……………..….……... 205
第四篇 化合物之物理化學性質及光譜數據..……….….…………..….……... 208
參 考 文 獻…..………………………………………………………….……... 252
論文著作及發表…………………………………………………………………..261

圖 表 目 錄
表目錄
表1-1台灣產石竹科植物一覽………………………………….………..…..……….7~8
表1-2 由Drymaria 屬所分離得到之化合物及其基源………………………………...11
表1-3 由Dianthus 屬所分離得到之化合物、分類及其基源…………………......13~15
表1-4 氨基酸之1H與13C NMR之特徵訊號表……………………………………….30
表1-5 氨基酸之分子量與其L、D form於HPLC之滯留時間表………………………31
表1-6 氨基酸之L、D form於chiral TLC(CHIRALPLATE)之Rf值…………………32
表1-7 各類型之β-Turns與α-turns的立體指標數據……..………………………..…39
表1-8以3JNHHα= 6.4 cos2θ-1.4 cosθ+1.9公式所計算之angles與coupling constants對應表…….………………………………………………………..….40
表1-9 各對照標準之13C NMR chemical shifts…………..……………………………41
表1-10 各氨基酸之標準13C NMR chemical shifts值…………………………………42
表1-11 各peptides構型之amide band I於IR光譜中的吸收值…………………….43
表2-1 菁芳草(D. diandra) 成分分離之成果……….…………………………………..61
表2-2 瞿麥(D. superbus) 成分分離之成果……….…………………………………...62
表2-3 長萼瞿麥(D. superbus var. longicalycinus)成分分離之成果….….……….….62
表3-1 Diandrine A之1H 及13C NMR光譜數據......................................................78
表3-2 Diandrine B之1H 及13C NMR光譜數據.....................................................86
表3-3 Diandrine C之1H 及13C NMR光譜數據.....................................................93
表3-4 Diandrine D之1H 及13C NMR光譜數據...................................................101
表3-5 Dianthin C之1H 及13C NMR光譜數據.......................................................109
表3-6 Dianthin E之1H 及13C NMR光譜數據........................................................123
表3-7 Longicalycinin A之1H 及13C NMR光譜數據...............................................133
表3-8 Drymaritin(DR-15)之光譜數據....................................................................143
表3-9 天然物細胞毒殺作用之篩檢結果….……………………………………………153
表4-1 合成之Dianthramide Alkaloid Methyl Ester化合物………………………….157
表4-2 合成之2-Phenyl-substituted bezoxazinones化合物………………………...165
表4-3 合成之2- Substituted bezoxazinones化合物………………………………...166
表4-4 合成之2-Substituted naphtha[1,2-d]oxazinones化合物…..……………….183
表4-5 合成之2-Substituted naphtha[2,3-d]oxazinones 化合物…………………...184
表4-6 Dianthramide及其類似物抗血小板凝集作用篩檢結果………….………….198
表4-7 Dianthramide及其類似物人類嗜中性白血球(Neutrophils) Superoxide Generation抑制作用篩檢結果…..………………………………...…………..199
表4-8 Dianthramide及其類似物人類嗜中性白血球elastase釋放抑制作用之篩檢結果…………...…………………………………………………………………….200
表4-9 Dianthramide及其類似物cytotoxicity作用篩檢結果……….……………….202
表4-10 Dianthramide及其類似物抗人類冠狀病毒活性篩檢結果…………….…….203


圖目錄
圖1-2-1 菁芳草植株圖……………………………………………………..……………..9
圖1-2-2 瞿麥植株圖與中藥瞿麥圖…………………….………………………… ……10
圖1-2-3 長萼瞿麥植株圖……………………………….…………….…………………10
圖1-3-1 由Drymaria 屬所分離得到之化合物…………….……………………...12~13
圖1-3-2 由Dianthus 屬所分離得到之化合物…………….………………..…….16~24
圖1-4-1 Cyclic Peptide 化學結構分類樹狀圖…………………….….......................25
圖1-4-2 Cyclic Peptide 化學結構分類……………….………............................26~28
圖1-4-3 Ninhydrin test之反應與檢測原理………….……….………........................29
圖1-4-4 Peptides於質譜下所產生之離子片段種類.……….………..........................33
圖1-4-5 Peptides以串聯質譜所產生之離子片段….……….….................................34
圖1-4-6 Edman degradation之原理與機轉……….……….….................................35
圖1-4-7 Peptide bond及 proline之trans form/ cis form...……...............................36
圖1-4-8 α-Helix,β-sheet與β-turn之標準CD光譜圖...……….................................37
圖1-4-9 310-Helix之標準CD光譜圖...………..........................................................38
圖1-4-10 氨基酸的dihedral angles...………..........................................................38
圖1-4-11 各類型β-turn之分子模擬圖………..........................................................39
圖1-4-12 Cyclopeptide alkaloids中β-OH氨基酸configuration解析.......................44
圖3-1-1 Diandrine A (DR-23)之IR光譜圖………………..………………………..... .73
圖3-1-2 Diandrine A (DR-23)之1H-NMR 光譜圖……….….…………….……….. ...73
圖3-1-3 Diandrine A (DR-23)之13C NMR 與DEPT 光譜圖……………………….. 74
圖3-1-4 Diandrine A (DR-23)之HMQC 光譜圖……………………………………... 74
圖3-1-5 Diandrine A (DR-23)之HMBC光譜圖………………………………………..75
圖3-1-6 Diandrine A (DR-23)之TOCSY 光譜圖…………….………………………..75
圖3-1-7 Diandrine A (DR-23)之ROESY光譜圖………………………………………76
圖3-1-8 Diandrine A (DR-23)之CD光譜圖………………….………………………...76
圖3-1-9 Diandrine A (DR-23)之Molecular-modeling………….………………………77
圖3-1-10 Diandrine A (DR-23)之FABMS光譜圖…………….……………………….77
圖3-2-1 Diandrine B (DR-22)之IR光譜圖……………………………………………. 81
圖3-2-2 Diandrine B (DR-22)之1H-NMR 光譜圖……….…………………….….… 81
圖3-2-3 Diandrine B (DR-22)之13C NMR光譜圖……….……………….…………. 82
圖3-2-4 Diandrine B (DR-22)之HMQC 光譜圖………………………………..……. 82
圖3-2-5 Diandrine B (DR-22)之HMBC光譜圖……………………………………….83
圖3-2-6 Diandrine B (DR-22)之TOCSY 光譜圖……………………………………..83
圖3-2-7 Diandrine B (DR-22)之FABMS光譜圖………………………………………84
圖3-2-8 Diandrine B (DR-22)之ROESY光譜圖………………………………………84
圖3-2-9 Diandrine B (DR-22)之CD光譜圖……………………………………………85
圖3-3-1 Diandrine C (DR-28)之IR光譜圖……………………………..…………….. 88
圖3-3-2 Diandrine C (DR-28)之1H-NMR 光譜圖……….…………………………... 89
圖3-3-3 Diandrine C (DR-28)之13C NMR光譜圖…..….……….………...…………89
圖3-3-4 Diandrine C (DR-28)之HETCOR 光譜圖………………..……..…..………90
圖3-3-5 Diandrine C (DR-28)之HMBC光譜圖………….……………………..….... 90
圖3-3-6 Diandrine C (DR-28)之TOCSY 光譜圖…………………….……………….91
圖3-3-7 Diandrine C (DR-28)之ESIMS/MS光譜圖……………………….…………91
圖3-3-8 Diandrine C (DR-28)之ROESY光譜圖……………………………………..92
圖3-3-9 Diandrine C (DR-28)之CD光譜圖…………………………………………..92
圖3-4-1 Diandrine D (DR-29)之1H-NMR 光譜圖…………….…………..…………..96
圖3-4-2 Diandrine D (DR-29)之13C NMR光譜圖……………………………….……96
圖3-4-3 Diandrine D (DR-29)之IR光譜圖………………….………………….……..97
圖3-4-4 Diandrine D (DR-29)之HMQC 光譜圖………..………………….…………97
圖3-4-5 Diandrine D (DR-29)之HMBC光譜圖……………………………………….98
圖3-4-6 Diandrine D (DR-29)之TOCSY 光譜圖……………………………………..98
圖3-4-7 Diandrine D (DR-29)之ESIMS/MS光譜圖…………………………………..99
圖3-4-8 Diandrine D (DR-29)之ROESY光譜圖………………………………………99
圖3-4-9 Diandrine D (DR-29)之CD光譜圖…………….……………………………100
圖3-4-10 Diandrine D(DR-29)與Diandrine C (DR-28)之1H NMR 光譜比較….100
圖3-5-1 Dianthin C (DS-P6)之1H-NMR 光譜圖………………………………….…104
圖3-5-2 Dianthin C (DS-P6)之13C NMR與DEPT光譜圖….……………………...104
圖3-5-3 Dianthin C (DS-P6)之IR光譜圖……….…………….………………….…..105
圖3-5-4 Dianthin C (DS-P6)之HMQC 光譜圖…………….………….….…………105
圖3-5-5 Dianthin C (DS-P6)之HMBC光譜圖……….………………………………106
圖3-5-6 Dianthin C (DS-P6)之TOCSY 光譜圖…………………….……….………106
圖3-5-7 Dianthin C (DS-P6)之ESIMS/MS光譜圖…………………………….……107
圖3-5-8 Dianthin C (DS-P6)之ROESY光譜圖…………………….………………..107
圖3-5-9 Dianthin C (DS-P6)之CD光譜圖……………….………….……………….108
圖3-6-1 Dianthin D (DS-P3)之ESIMS/MS光譜圖….……………….……………...112
圖3-6-2 Dianthin D (DS-P3)之1H NMR光譜圖….…………………….…………….113
圖3-6-3 Dianthin D (DS-P3)之13C NMR光譜圖……………………….….………...113
圖3-6-4 Dianthin D (DS-P3)之IR光譜圖…………………………………….……….114
圖3-6-5 Dianthin D (DS-P3)之ROESY光譜圖………………………………………114
圖3-6-6 Dianthin D (DS-P3)之CD光譜圖……………………………………………115
圖3-7-1 Dianthin E (DS-P4)之ESIMS/MS光譜圖………………………..…..….….118
圖3-7-2 Dianthin E (DS-P4)之IR光譜圖…………………………………..…………118
圖3-7-3 Dianthin E (DS-P4)之1H NMR光譜圖.…………………….….……………119
圖3-7-4 Dianthin E (DS-P4)之13C NMR光譜圖.…………………………………….119
圖3-7-5 Dianthin E (DS-P4)之HMQC光譜圖…..…..………………….……………120
圖3-7-6 Dianthin E (DS-P4)之HMBC光譜圖…….……………….…………………120
圖3-7-7 Dianthin E (DS-P4)之TOCSY光譜圖..………..……………………………121
圖3-7-8 Dianthin E (DS-P4)之ROESY光譜圖…..……..……..……….……………121
圖3-7-9 Dianthin E (DS-P4)之CD光譜圖……………………………………………122
圖3-8-1 Dianthin F (DS-P5)之IR光譜圖……………………………….…………….126
圖3-8-2 Dianthin F (DS-P5)之1H NMR光譜圖………………………………………126
圖3-8-3 Dianthin F (DS-P5)之13C NMR光譜圖………………………….………….127
圖3-8-4 Dianthin F (DS-P5)之ESIMS/MS光譜圖…………………………………..127
圖3-9-1 Longicalycinin A (DS-P7)之IR光譜圖……………………...………………130
圖3-9-2 Longicalycinin A (DS-P7)之1H NMR光譜圖……………………..….…….130
圖3-9-3 Longicalycinin A (DS-P7)之13C NMR光譜圖………………….…………..131
圖3-9-4 Longicalycinin A (DS-P7)之ESIMS/MS光譜圖.……………...……………131
圖3-9-5 Longicalycinin A (DS-P7)之TOCSY光譜圖..……………….……………..132
圖3-9-6 Longicalycinin A (DS-P7)之ROESY光譜圖……………….…………..…..132
圖3-10-1 2’-Methoxydianthramide B (DS-A12)之EIMS光譜圖…...………………135
圖3-10-2 2’-Methoxydianthramide B (DS-A12)之IR光譜圖……………………….135
圖3-10-3 2’-Methoxydianthramide B (DS-A12)之1H NMR光譜圖………………..136
圖3-10-4 2’-Methoxydianthramide B (DS-A12)之13C NMR/DEPT光譜圖……….136
圖3-11-1 Drymaritin (DR-15)之IR光譜圖……………………………………………138
圖3-11-2 Drymaritin (DR-15)之EIMS光譜圖………………………………………..139
圖3-11-3 Drymaritin (DR-15)之1H NMR光譜圖……………………………………..139
圖3-11-4 Drymaritin (DR-15)之13C NMR光譜圖……………………………………140
圖3-11-5 Drymaritin (DR-15)之NOESY NMR光譜圖………………………………140
圖3-11-6 Drymaritin (DR-15)之HMQC NMR光譜圖………………………………..141
圖3-11-7 Drymaritin (DR-15)之1H-13C HMBC NMR光譜圖……………………….141
圖3-11-8 Drymaritin (DR-15)之1H-15N HMBC NMR光譜圖………………………..142
圖3-12-1 Diandraflavone (DR-31)之IR光譜圖………………………………………145
圖3-12-2 Diandraflavone (DR-31)之FABMS光譜圖….…..………………………..146
圖3-12-3 Diandraflavone (DR-31)之1H NMR光譜圖……………………………….146
圖3-12-4 Diandraflavone (DR-31)之13C NMR與DEPT光譜圖…………………..147
圖3-12-5 Diandraflavone (DR-31)之HMQC光譜圖…….…………………………..147
圖3-12-6 Diandraflavone (DR-31)之HMBC光譜圖……...…………………………148
圖3-12-7 Diandraflavone (DR-31)之NOESY光譜圖……………………………….148
圖4-1-1 Dianthramide alkaloids chemical transformation…..…………….………..154
圖4-1 DS-R1之1H NMR光譜圖………………………………………………………157
圖4-2 DS-R2之1H NMR光譜圖………………………………………………………158
圖4-3 DS-R3之1H NMR光譜圖………………………………………………………158
圖4-4 DS-R4之1H NMR光譜圖………………………………………………………159
圖4-5 DS-R5之1H NMR光譜圖………………………………………………………159
圖4-6 DS-R6之1H NMR光譜圖………………………………………………………160
圖4-7 DS-R7之1H NMR光譜圖………………………………………………………160
圖4-8 DS-R8之1H NMR光譜圖………………………………………………………161
圖4-9 DS-R9之1H NMR光譜圖………………………………………………………161
圖4-10 DS-R10之1H NMR光譜圖……………………………………………………162
圖4-11 DS-R11之1H NMR光譜圖……………………………………………………162
圖4-12 DS-R12之1H NMR光譜圖……………………………………………………163
圖4-13 DS-R13之1H NMR光譜圖……………………………………………………163
圖4-14 DS-R14之1H NMR光譜圖……………………………………………………164
圖4-15 DS-R15之1H NMR光譜圖……………………………………………………166
圖4-16 DS-R16之1H NMR光譜圖……………………………………………………167
圖4-17 DS-R17之1H NMR光譜圖……………………………………………………167
圖4-18 DS-R18之1H NMR光譜圖……………………………………………………168
圖4-19 DS-R19之1H NMR光譜圖……………………………………………………168
圖4-20 DS-R20之1H NMR光譜圖……………………………………………………169
圖4-21 DS-R21之1H NMR光譜圖……………………………………………………169
圖4-22 DS-R22之1H NMR光譜圖……………………………………………………170
圖4-23 DS-R23之1H NMR光譜圖……………………………………………………170
圖4-24 DS-R24之1H NMR光譜圖……………………………………………………171
圖4-25 DS-R25之1H NMR光譜圖……………………………………………………171
圖4-26 DS-R26之1H NMR光譜圖……………………………………………………172
圖4-27 DS-R27之1H NMR光譜圖……………………………………………………172
圖4-28 DS-R28之1H NMR光譜圖……………………………………………………173
圖4-29 DS-R29之1H NMR光譜圖……………………………………………………173
圖4-30 DS-R30之1H NMR光譜圖……………………………………………………174
圖4-31 DS-R31之1H NMR光譜圖……………………………………………………174
圖4-32 DS-R32之1H NMR光譜圖……………………………………………………175
圖4-33 DS-R33之1H NMR光譜圖……………………………………………………175
圖4-34 DS-R34之1H NMR光譜圖……………………………………………………176
圖4-35 DS-R35之1H NMR光譜圖……………………………………………………176
圖4-36 DS-R36之1H NMR光譜圖……………………………………………………177
圖4-37 DS-R37之1H NMR光譜圖……………………………………………………177
圖4-38 DS-R38之1H NMR光譜圖……………………………………………………178
圖4-39 DS-R39之1H NMR光譜圖……………………………………………………178
圖4-40 DS-R40之1H NMR光譜圖……………………………………………………179
圖4-41 DS-R41之1H NMR光譜圖……………………………………………………179
圖4-42 DS-R42之1H NMR光譜圖……………………………………………………180
圖4-43 DS-R43之1H NMR光譜圖……………………………………………………180
圖4-44 DS-R44之1H NMR光譜圖……………………………………………………181
圖4-45 DS-R45之1H NMR光譜圖……………………………………………………181
圖4-46 DS-R46之1H NMR光譜圖……………………………………………………182
圖4-47 DS-R47之1H NMR光譜圖……………………………………………………182
圖4-48 DS-R48之1H NMR光譜圖……………………………………………………183
圖4-49 DS-R49之1H NMR光譜圖……………………………………………………185
圖4-50 DS-R50之1H NMR光譜圖……………………………………………………185
圖4-51 DS-R51之1H NMR光譜圖……………………………………………………186
圖4-52 DS-R52之1H NMR光譜圖……………………………………………………186
圖4-53 DS-R53之1H NMR光譜圖……………………………………………………187
圖4-54 DS-R54之1H NMR光譜圖……………………………………………………187
圖4-55 DS-R55之1H NMR光譜圖……………………………………………………188
圖4-56 DS-R56之1H NMR光譜圖……………………………………………………188
圖4-57 DS-R57之1H NMR光譜圖……………………………………………………189
圖4-58 DS-R58之1H NMR光譜圖……………………………………………………189
圖4-59 DS-R59之1H NMR光譜圖……………………………………………………190
圖4-60 DS-R60之1H NMR光譜圖……………………………………………………190
圖4-61 DS-R61之1H NMR光譜圖……………………………………………………191
圖4-62 DS-R62之1H NMR光譜圖……………………………………………………191
圖4-63 DS-R63之1H NMR光譜圖……………………………………………………192
圖4-64 DS-R64之1H NMR光譜圖……………………………………………………192
圖4-65 DS-R65之1H NMR光譜圖……………………………………………………193
圖4-66 DS-R66之1H NMR光譜圖……………………………………………………193
圖4-67 DS-R67之1H NMR光譜圖……………………………………………………194
圖4-68 DS-R68之1H NMR光譜圖……………………………………………………194
圖4-69 DS-R69之1H NMR光譜圖……………………………………………………195
圖4-70 DS-R70之1H NMR光譜圖……………………………………………………195
圖4-71 DS-R71之1H NMR光譜圖……………………………………………………196
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