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研究生:黃珮茹
研究生(外文):Pei-Ru Huang
論文名稱:魚腥草與葎草之化學成分研究
論文名稱(外文):Studies on the Chemical Constituents of Houttuynia cordata Thunb. and Humulus scandens (Lour.) Merr.
指導教授:廖志中廖志中引用關係
學位類別:碩士
校院名稱:中國醫藥大學
系所名稱:藥物化學研究所
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:2008
畢業學年度:96
語文別:中文
論文頁數:202
中文關鍵詞:魚腥草三白草科葎草大麻科
外文關鍵詞:Houttuynia cordata ThunbSaururaceaeHumulus scandensCannabaceae
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第一部份 魚腥草之化學成分研究
以甲醇萃取魚腥草 (Houttuynia cordata Thunb.) 的全草,經由管柱層析與高效液相層析儀分離純化,共得到十個化合物。經光譜分析及文獻比對後,確認其化學結構為 : 兩個aristolactam型骨架生物鹼:aristolactam BⅡ(2)、aristolactam AⅡ(5);一個oxoaporphine型骨架生物鹼:splendidine (10);三個4,5-dioxoaporphine型骨架生物鹼:cepharadione B (1)、piperadione (3)、norcepharadione B (4);兩個flavonoid型骨架黃酮類:quercitrin (6)、quercetin-3-O-β-D-galactoside (7);一個benzenoid型骨架化合物:caffeic acid (8);一個amide型骨架化合物:benzamide (9)
由魚腥草所分離得到之化合物歸納得知,魚腥草主要的成分為生物鹼和黃酮兩大類,其中piperadione (3)及caffeic acid (8) 為首次從魚腥草分離得到之化合物。

第二部份 葎草之化學成分研究
以甲醇萃取葎草 (Humulus scandens (Lour.) Merr.) 的全草,經由管柱層析與高效液相層析儀分離純化,共得到五個化合物,經光譜分析及文獻比對後,確認其化學結構為β-stiosteryl-3-O-β-D-glucoside (a), sucrose (b), myo-inositol (c), 3-hydroxy-4,4-dimethyl-4-butyrolactone (d), 2,3-dihydroxy-2-methylbutyrolactone (e)。
第一部份 魚腥草之化學成分研究
In the present investigation, the whole plant of Houttuynia cordata Thunb. was collected and extracted with methanol. The extracts were further separated by column chromatography and high performance liquid chromatography. Ten compounds were isolated, and they contain two aristolactams: aristolactam BⅡ(2) and aristolactam AⅡ(5); one oxoap- orphine: splendidine (10); three 4,5-dioxoaporphines: cepharadione B (1), piperadione (3) and norcepharadione B (4); two flavonoids: quercitrin (6) and quercetin-3-O-β-D-galactoside (7); one benzenoid: caffeic acid (8); one amide: benzamide (9)。
These compounds were characterized by comprehensive analysis of their 1D and 2D NMR and mass spectra. Among them, piperadione (3) and caffeic acid (8) are isolated from Houttuynia cordata for the first time.

第二部份 葎草之化學成分研究
In the present investigation, the whole plant of Humulus scan- dens (Lour.) Merr. was collected and extracted with methanol. The extracts were further separated by column chromatography and high performance liquid chromatography. Five compounds: β-stiosteryl-3-O-β-D-glucoside (a), sucrose (b), myo-inositol (c), 3-hydroxy-4,4-dimethyl-4-butyrolactone (d), 2,3-dihydroxy-2- methylbutyrolactone (e) were isolated from Humulus scandens (Lour.) Merr.
The structural elucidation of the isolated natural products were established by spectral methods.
目 錄
第一部份 魚腥草之化學成分研究
中文摘要……………………………………………………1
英文摘要……………………………………………………2
第一章 緒論…………………………………………………3
第一節 前言…………………………………………3
第二節 植物型態分佈及應用………………………5
第三節 研究背景……………………………………8
第四節 魚腥草之成分研究與文獻整理……………9
第五節 蕺菜屬植物之藥理研究回顧………………22
第六節 研究目的與動機……………………………27
第二章 實驗流程與步驟…………………………………28
第一節 植物成分之萃取與分離流程………………28
第三章 化合物之結構解析……………………………35
第一節 Aristolactam型骨架化合物……………35
壹、Aristolactam型骨架化合物之圖譜特徵……………35
貳、Aristolactam型骨架化合物之光譜整理…………37
叁、Aristolactam型骨架化合物之結構解析………41
一、Aristolactam BⅡ(2) 之結構解析………………41
二、Aristolactam AⅡ(5) 之結構解析………………48
第二節 Oxoaporphine型骨架化合物…………………55
壹、Oxoaporphine型骨架化合物之圖譜特徵…………55
貳、Oxoaporphine型骨架化合物之結構解析…………57
一、Splendidine (10) 之結構解析…………………57
第三節 4, 5-Dioxoaporphine型骨架化合物………64
壹、4, 5-Dioxoaporphine型骨架化合物之圖譜特徵……64
貳、4, 5-Dioxoaporphine型骨架化合物之光譜整理……66
叁、4, 5-Dioxoaporphine 型骨架化合物之結構解析…70
一、Cepharadione B (1) 之結構解析……………70
二、Piperadione (3) 之結構解析…………………74
三、Norcepharadione B (4) 之結構解析……………77
第四節 Flavonoid型骨架化合物…………………84
壹、Flavonoid型骨架化合物之圖譜特徵………………84
貳、 Flavonoid型骨架化合物之光譜整理……………87
叁、Flavonoid型骨架化合物之結構解析……………94
一、Quercitrin (6) 之結構解析……………………94
二、Quercetin-3-O-β-D-galactoside (7) 之結構解析.99
第五節 Amide型骨架化合物……………………107
一、Benzamide (9) 之結構解析……………………107
第四章 生物活性試驗………………………………111
第五章 結論…………………………………………114
第六章 實驗相關部分…………………………………117
第一節 實驗材料與儀器…………………………117
第二節 各化合物之物理與光譜數據總整理………121
第七章 參考文獻……………………………………131

圖表目錄
表一 : 三百草科植物-四屬六種……………………………8
表二 : 蕺菜屬植物之藥理文獻整理………………………22
表三 : 由Houttuynia cordata分離得到之化合物結構…33
表四 : Aristolactam之 1H-NMR光譜數據整理.................38
表五 : Aristolactam之 13C-NMR光譜數據整理...............39
表六 : Aristolactam BⅡ(2) 之1H及13C-NMR光譜數據…..43
表七 : Aristolactam AⅡ(5) 之1H及13C-NMR光譜數據....50
表八 : Splendidine (10) 之1H及13C-NMR光譜數據……59
表九 : 4,5-Dioxoaporphines之 1H-NMR光譜數據整理......67
表十 : 4,5-Dioxoaporphine之 13C-NMR光譜數據整理.......68
表十一 : Cepharadione B (1) 之1H及13C-NMR光譜數據...71
表十二 : 化合物 (3) 與Piperadione之1H-NMR光譜數據比
較......75
表十三 : Norcepharadione B (4) 之1H及13C-NMR光譜數據
...................................79
表十四 : 第3位碳上接醣的Flavonoid之 1H-NMR光譜數據
整理...........................................88
表十五 : 第3位碳上接醣的Flavonoid之 13C-NMR光譜數據
整理.................................89
表十六 : 第7位碳上接醣的Flavonoid之 1H-NMR光譜數據
整理.................................91
表十七 : 第7位碳上接醣的Flavonoid之 13C-NMR光譜數
據整理...............................92
表十八 : Quercitrin (6) 之1H及13C-NMR光譜數據...........96
表十九 : Quercetin-3-O-β-D-galactoside (7) 之1H及13C-NMR
光譜數據..................................................101
表二十 : Benzamide (9) 之1H及13C-NMR光譜數據.........107
圖一 : 魚腥草植物之外觀……………………………………6
圖二 : 魚腥草植物之乾品……………………………………6
圖三 : 魚腥草植物之外觀繪圖………………………………7
圖四 : 分離流程……………………………………………..28
圖五 : 分離流程……………………………………………..29
圖六 : 分離流程……………………………………………..30
圖七 : 分離流程……………………………………………..31
圖八 : 分離流程……………………………………………..32
圖九 : 分離流程……………………………………………..33
圖十 : Aristolactam BⅡ(2) 之COSY與NMBC關係……..42
圖十一 : Aristolactam BⅡ(2) 之FAB-MS光譜圖…………43
圖十二 : Aristolactam BⅡ(2) 之IR光譜圖………………...44
圖十三 : Aristolactam BⅡ(2) 之UV光譜圖………………44
圖十四 : Aristolactam BⅡ(2) 之1H-NMR光譜圖…………45
圖十五 : Aristolactam BⅡ(2) 之13C-NMR光譜圖………...45
圖十六 : Aristolactam BⅡ(2) 之HSQC光譜圖……………46
圖十七 : Aristolactam BⅡ(2) 之HMBC光譜圖…………...46
圖十八 : Aristolactam BⅡ(2) 之COSY光譜圖……………47
圖十九 : Aristolactam BⅡ(2) 之ROESY光譜圖…………..47
圖二十 : Aristolactam AⅡ(5) 之COSY與NMBC關係……49
圖二十一 : Aristolactam AⅡ(5) 之EI-MS光譜圖…………50
圖二十二 : Aristolactam AⅡ(5) 之IR光譜圖……………...51
圖二十三 : Aristolactam AⅡ(5) 之UV光譜圖…………….51
圖二十四 : Aristolactam AⅡ(5) 之1H-NMR光譜圖………52
圖二十五 : Aristolactam AⅡ(5) 之13C-NMR光譜圖……...52
圖二十六 : Aristolactam AⅡ(5) 之HSQC光譜圖…………53
圖二十七 : Aristolactam AⅡ(5) 之HMBC光譜圖………...53
圖二十八 : Aristolactam AⅡ(5) 之COSY光譜圖…………54
圖二十九 : Aristolactam AⅡ(5) 之NOESY光譜圖………..54
圖三十 : Splendidine (10) 之NMBC關係………….............58
圖三十一 : Splendidine (10) 之ESI-MS光譜圖…………....60
圖三十二 : Splendidine (10) 之UV光譜圖…………...........60
圖三十三 : Splendidine (10) 之1H-NMR光譜圖…………..61
圖三十四 : Splendidine (10) 之13C-NMR光譜圖………….61
圖三十五: Splendidine (10) 之HSQC光譜圖…………........62
圖三十六 : Splendidine (10) 之HMBC光譜圖………….....62
圖三十七 : Splendidine (10) 之NOESY光譜…………........63
圖三十八 : Cepharadione B (1) 之EI-MS光譜圖………….72
圖三十九: Cepharadione B (1) 之UV光譜圖……………….72
圖四十 : Cepharadione B (1) 之1H-NMR光譜圖…………..73
圖四十一 : Cepharadione B (1) 之13C-NMR光譜圖………73
圖四十二 : Piperadione (3) 之EI-MS光譜圖………………75
圖四十三 : Piperadione (3) 之UV光譜圖………………….76
圖四十四 : Piperadione (3) 之1H-NMR光譜圖……………76
圖四十五 : Norcepharadione B (4) 之COSY與NMBC關係
…………………………………………………...78
圖四十六 : Norcepharadione B (4) 之ESI-MS光譜圖…......79
圖四十七 : Norcepharadione B (4) 之UV光譜圖…............0
圖四十八 : Norcepharadione B (4) 之1H-NMR光譜圖…....80
圖四十九 : Norcepharadione B (4) 之13C-NMR光譜圖…...81
圖五十 : Norcepharadione B (4) 之HSQC光譜圖…............81
圖五十一 : Norcepharadione B (4) 之HMBC光譜圖….......82
圖五十二 : Norcepharadione B (4) 之COSY光譜圖…........82
圖五十三 : Norcepharadione B (4) 之ROESY光譜圖…......83
圖五十四 : Quercitrin (6) 之EI-MS光譜圖…...........96
圖五十五: Quercitrin (6) 之IR光譜圖…....................97
圖五十六 : Quercitrin (6) 之UV光譜圖…................97
圖五十七 : Quercitrin (6) 之1H-NMR光譜圖….........98
圖五十八 : Quercitrin (6) 之13C-NMR光譜圖….........98
圖五十九 : Quercetin-3-O-β-D- galactoside (7) 之COSY與
NMBC關係…………………………………….100
圖六十 : Quercetin-3-O-β-D-galactoside (7) 之ESI-MS光譜
圖………………………………………………….102
圖六十一 : Quercetin-3-O-β-D-galactoside (7) 之IR光譜圖
………………………………………………….102
圖六十二 : Quercetin-3-O-β-D-galactoside (7) 之UV光譜圖
………………………………………………….103
圖六十三 : Quercetin-3-O-β-D-galactoside (7) 之1H-NMR光
譜圖…………………………………………….103
圖六十四 : Quercetin-3-O-β-D-galactoside (7) 之13C-NMR光
譜圖…………………………………………….104
圖六十五 : Quercetin-3-O-β-D-galactoside (7) 之HSQC光譜
圖……………………………………………….104
圖六十六 : Quercetin-3-O-β-D-galactoside (7) 之HMBC光譜
圖……………………………………………….105
圖六十七 : Quercetin-3-O-β-D-galactoside (7) 之COSY光譜
圖……………………………………………….105
圖六十八 : Quercetin-3-O-β-D-galactoside (7) 之NOESY光
譜圖…………………………………………….106
圖六十九 : Benzamide (9) 之EI-MS光譜圖……………...108
圖七十 : Benzamide (9) 之IR光譜圖……………………..108
圖七十一 : Benzamide (9) 之UV光譜圖…………………109
圖七十二 : Benzamide (9) 之1H-NMR光譜圖……………109
圖七十三 : Benzamide (9) 之13C-NMR光譜圖…………..110

第二部份 葎草之化學成分研究
中文摘要…………………………………………………142
英文摘要…………………………………………………143
第一章 緒論………………………………………………144
第一節 前言………………………………………….144
第二節 植物型態分佈及應用……………………….145
第三節 研究背景…………………………………….148
第四節 葎草屬之成分研究與文獻整理…………….149
第五節 葎草屬植物之藥理研究回顧……………….158
第六節 研究目的與動機…………………………….161
第二章 實驗流程與步驟………………………………162
第一節 植物成分之萃取與分離流程………………162
第三章 化合物之結構解析……………………………168
第一節 β-Stiosteryl-3-O-β-D-glucoside (a) 之結構解析
………………………………………………168
第二節 Sucrose (b) 之結構解析…………………….175
第三節 myo-Inositol (c) 之結構解析………………179
第四章 生物活性試驗………………………………….185
第五章 結論……………………………………………187
第六章 實驗相關部分…………………………………188
第一節 實驗材料與儀器…………………………….188
第二節 各化合物之物理與光譜數據總整理……….192
第七章 參考文獻…………………………………………197

圖表目錄
表一 : 大麻科植物-兩屬五種……………………………148
表二 : 葎草屬植物之藥理文獻整理……………………158
表三 : 由Humulus scandens的葉部分離出3個化合物…166
表四 : 由Humulus scandens的莖部分離出2個化合物......167
表五 : β-Stiosteryl-3-O-β-D-glucoside (a) 之1H及13C-NMR
光譜數據..............................170
表六 : Sucrose (b) 之1H及13C-NMR光譜數據.............176
表七 : myo-Inositol (c) 之1H及13C-NMR光譜數據..........180
表八 : Inositols之 1H, 13C-NMR光譜數據整理.......181
圖一 : 葎草植物之外觀……………………………………146
圖二 : 葎草之花及花穗……………………………………146
圖三 : 葎草植物之外觀繪圖………………………………147
圖四 : 分離流程……………………………………………163
圖五 : 分離流程……………………………………………164
圖六 : 分離流程……………………………………………164
圖七 : 分離流程……………………………………………165
圖八 : 分離流程……………………………………………166
圖九 : β-Stiosteryl-3-O-β-D-glucoside (a) 之NMBC關係.169
圖十 : β-Stiosteryl-3-O-β-D-glucoside (a) 之EI-MS光譜圖
……………………………………………………171
圖十一 : β-Stiosteryl-3-O-β-D-glucoside (a) 之IR光譜圖
…………………………………………………..171
圖十二 : β-Stiosteryl-3-O-β-D-glucoside (a) 之UV光譜圖
……………………………………………………172
十三 : β-Stiosteryl-3-O-β-D-glucoside (a) 之1H-NMR光譜
圖…………………………………………………172
圖十四 : β-Stiosteryl-3-O-β-D-glucoside (a) 之13C-NMR光譜
圖…………………………………………………173
圖十五 : β-Stiosteryl-3-O-β-D-glucoside (a) 之HSQC光譜圖
……………………………………………………..173
圖十六 : β-Stiosteryl-3-O-β-D-glucoside (a) 之HMBC光譜圖
……………………………………………………174
圖十七 : Sucrose (b) 之IR光譜圖…………………………176
圖十八 : Sucrose (b) 之UV光譜圖………………………177
圖十九 : Sucrose (b) 之1H-NMR光譜圖………………….177
圖二十 : Sucrose (b) 之13C-NMR光譜圖…………………178
圖二十一 : myo-Inositol (c) 之NOESY關係……………180
圖二十二 : myo-Inositol (c) 之ESI-MS光譜圖…………182
圖二十三 : myo-Inositol (c) 之IR光譜圖…………………182
圖二十四 : myo-Inositol (c) 之UV光譜圖………………183
圖二十五 : myo-Inositol (c) 之1H-NMR光譜圖…………183
圖二十六 : myo-Inositol (c) 之13C-NMR光譜圖…………184
圖二十七 : myo-Inositol (c) 之NOESY光譜圖…………184
第一部份 魚腥草之化學成分研究
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p.59渡假出版社有限公司
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botany, National Taiwan University, Taipei, Taiwan
R.O.C.,. Flora of Taiwan 1996, vol.2, (second edition), p.621.
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