臺灣博碩士論文加值系統

辣木（Moringa oleifera Lam）根皮甲醇粗萃物氯仿層對具有艾黴素（doxorubicin）抗藥性的人類乳腺癌細胞（MCF-7/ADR）及老鼠肺纖維化細胞（MLF）具有明顯的細胞毒殺活性，因此本研究選定辣木進行成分研究，希望藉此了解其化學組成。將辣木根皮與莖皮分別利用甲醇熱迴流萃取，分配萃取後進行分離純化後，從辣木根皮與莖皮甲醇粗萃物分別鑑定出27與11個化合物，其中2個為天然界首次發現的新化合物，純化所得化合物將進一步送測藥理活性，希望藉此開發新的天然抗癌藥物。

芝麻（Sesamum indicum）種子甲醇粗萃物，經由分配萃取與各種層析方法進行分離純化，共鑑定出30個化合物，其中包括2個天然界首次發現的化合物與利用半合成反應所得的木酚素類化合物進行DPPH自由基捕捉、超氧陰離子抑制、亞鐵離子螯合能力及還原力實驗評估其抗氧化活性。結果顯示，除了sesamin及sesamolin等含量較多的木酚素之外，其他芝麻木酚素化合物如 (+)-pinoresinol、(-)-piperitol及(+)-(7S,8''R,8R)-acuminatolide都具有顯著的抗氧化活性，顯示其具有開發成為保健食品的潛力。

在有機蔬菜栽培田易發生由白菜炭疽菌（Colletotrichum higginsianum）引起的白菜炭疽病，因此本研究選用了五倍子、丁香、肉桂、大黃及虎杖等五種中藥材，利用高效能液相層析定量分析其粗萃物及分畫層中指標成分的含量，並進一步測試其粗萃物、分畫層與指標成分對白菜炭疽菌的抑菌活性，希望能藉此發現有效防治病害的成分，進而開發新的植物保護製劑。

In the preliminary cytotoxic bioassay, the chloroform layer of methanol extracts of M. oleifera demonstrated the significant cytotoxicity toward the doxorubicin resistant human breast adenocarcinoma cell lines (MCF-7/ADR) and rat pulmonary fibrosis cells (MLF). Therefore, the present research is aimed to purify and identify the constituents of M. oleifera. The methanol extracts of root barks and stem barks of M. oleifera were fractionated and further purified to afford 27 and 11 compounds, respectively. Among the isolates two compounds was reported from the natural sources for the first time. These isolates would be subjected into the biological activity examinations to explore new natural anticancer drugs.

The methanol extract of sesame (Sesamum indicum) seeds was fractionated and purified to afford 30 compounds. Among these isolates two were isolated from the natural sources for the first time. To evaluate their in vitro antioxidant potentials, the purified lignans and their derivative prepared by semi-synthesis were examined for the scavenging activities of DPPH free radicals and superoxide anions. Moreover, the capability of chelating ferrous ions and reducing power of these sesame lignans were also tested. The results suggest that, besides the well-known sesamolin and sesamin, the minor sesame lignans (+)-pinoresinol, (–)-piperitol and (+)-(7S,8''R,8R)-acuminatolide are also adequate active ingredients and may be potential sources for the development of healthy foods.

In the organic vegetables cultivation fields, the cabbage anthracnose caused by Colletotrichum higginsianum was a serious problem. Thus in the present study, five different traditional Chinese medicines, including Galla rhois, Eugenia caryophyllata Thunb., Cinnamomum cassia, Polygonum cuspidatum Sieb. et Zucc., and Rheum officinale Baillon were extracted and purified. The contents of indicator compounds in the crude extracts and fractions were analyzed with the aid of high-performance liquid chromatography. Furthermore, the antifungal activities of the crude extracts, fractions, and indicator compounds were examined to explore the active principles against C. higginsianum. From our research results, it is hopeful to discover new botanical pesticides derived from the plant sources.

摘要 ……………………………………...……………………………………… i

Abstract ………………………………...………………………………………… ii

誌謝 ……………………………………………................................................... iii
目錄 ……………………………………...……………………………………… iv

表目錄 …………………………………...…………………………………….... ix
圖目錄 …………………………………...…………………………………….... x

第壹篇 辣木根皮與莖皮之成分研究
第一章 緒論……………………………………………………...……………… 1
第二章 辣木屬植物研究回顧…………………………………..…………….... 3
第一節 辣木之植物形態……………………………………..…………...... 3
第二節 辣木屬植物之學名………………………………….……………… 5
第三節 辣木屬植物之藥理研究回顧………………………...…………….. 6
第四節 辣木屬植物之成分研究回顧………………………….…………… 17
第三章 辣木成分之抽取與分離…………………………………...………….... 26
第一節 辣木根皮成分之抽取與分離…………………………….………… 26
第二節 辣木莖皮成分之抽取與分離…………………………………….… 28
第四章 辣木成分之化學構造研究…………………………………….….......... 34
第一節 N-benzylcarbamic acid（80）之構造研究............................................ 34
第二節 4-(α-L-rhamnopyranosyloxy)benzaldehyde（88）之構造研究............ 36
第三節 benzyl β-D-arabinopyranosyl-(1→6)-β-D-glucopyranoside（91）之構造研究............................................................................................. 40
第四節 其他化合物之構造研究..................................................................... 44
第五章 結論……………………………………………...……………………… 45
第六章 實驗部份…………………...…………………………………………… 46
第一節 實驗所使用之儀器與藥品………………...……………………….. 46
第二節 辣木成分萃取與分離…………………...……..…………………… 47
第七章 光譜數據…………………………………………...…………………… 51
第貳篇 芝麻種子成分及其抗氧化活性研究
第一章 緒論………………………………………………...…………………… 60
第二章 胡麻屬植物研究回顧……………………………...………………….... 61
第一節 芝麻之植物形態………………………………...………………...... 61
第二節 胡麻屬植物之學名……………………………...………..………… 62
第三節 芝麻之藥理研究回顧…………………………..………………….. 63
第四節 胡麻屬植物之成分研究回顧…………………..…………..……… 64
第三章 芝麻種子成分之抽取與分離……………………………………….... 73
第四章 芝麻種子成分之化學構造研究……………………...………………… 79
第一節 samin (152) 之構造研究…………………..…...…………………... 79
第二節 disaminyl ether (153) 之構造研究....…………………….………… 84
第三節 其他化合物之構造研究...……......………....……………………… 86
第五章 芝麻木酚素類化合物之合成研究…………………..……………....... 87
第一節Sesamin (85) 利用重鉻酸鉀（K2Cr2O7）進行氧化反應…….............. 87
第二節Sesamin (85) 利用高錳酸鉀（KMnO4）進行氧化反應……............... 87
第三節Sesamolin (90) 利用高錳酸鉀（KMnO4）進行氧化反應.................... 88
第六章 芝麻木酚素類化合物之抗氧化活性研究………................................... 89
第一節 DPPH自由基捕捉活性（DPPH free radical scavenging）.................. 90
第二節 超氧陰離子抑制活性（superoxide anion inhibition）......................... 92
第三節 亞鐵離子螯合能力（chelation of ferrous ions）.................................. 94
第四節 還原力（reducing power）.................................................................... 96
第七章 結論........................................................................................................... 98
第八章 實驗部份................................................................................................... 99
第一節 實驗所使用之儀器與藥品................................................................. 99
第二節 芝麻成分萃取與分離........................................................................ 100
第三節 木酚素類衍生物之合成實驗............................................................. 104
3.1 (-)-aptosimon (156) 的製備.............................................................. 104
3.2 (-)-asarinin (165) 的製備.................................................................. 104
3.3 sesamol (166) 的製備....................................................................... 104
第四節 抗氧化生理活性實驗......................................................................... 104
4.1 DPPH自由基捕捉實驗................................................................... 104
4.2 超氧陰離子抑制實驗...................................................................... 105
4.3 亞鐵離子螯合能力實驗.................................................................. 105
4.4 還原力試驗...................................................................................... 105
第九章 光譜數據................................................................................................... 107


第参篇 中草藥萃取物抑制白菜炭疽菌活性成分研究
第一章 緒論…………………………………………………...………………… 113
第二章 藥材介紹……………………………………………….……………….. 115
第一節 五倍子………………………...…………………………………...... 115
第二節 丁香…………………………….…………………………..……...... 116
第三節 肉桂………………………………………………………………..... 117
第四節 虎杖……………………………….………………………...……..... 119
第五節 大黃……………………………….………………………...……..... 120
第三章 藥材指標成分定量分析……………….……………………………….. 123
第一節 五倍子……………………………...……………………………...... 123
1.1 分析條件之選擇與最佳化……….……………………….……… 123
1.2 檢量線之製作…………………..……………..……….…………. 124
1.3確效試驗…………………………..……………………….……… 126
1.4定量分析結果……………………..……………………………… 127
第二節 丁香………….……………………………………………..……...... 129
2.1 分析條件之選擇與最佳化……………………………….……… 129
2.2 檢量線之製作………………………………………….…………. 130
2.3確效試驗………………………………………………….……… 131
2.4 定量分析結果……………………………..……………………… 132
第三節 肉桂………………………………………..……………………..... 134
3.1 分析條件之選擇與最佳化……………………………….……… 134
3.2 檢量線之製作………………………………………….…………. 135
3.3確效試驗…………………...……………………………….…… 136
3.4定量分析結果…………………………………………………… 137
第四章 白菜炭疽菌抑菌活性測試…………………..…..……........................... 140
第一節 五倍子甲醇粗萃物、乙酸乙酯分畫層及水分畫層之抑菌試驗….. 140
第二節 丁香甲醇粗萃物、乙酸乙酯分畫層及水分畫層之抑菌試驗…….. 142
第三節 肉桂甲醇粗萃物、乙酸乙酯分畫層及水分畫層之抑菌試驗…….. 144
第四節 虎杖甲醇粗萃物、氯仿分畫層及水分畫層之抑菌試驗…..……… 146
第五節 大黃甲醇粗萃物、氯仿分畫層及水分畫層之抑菌試驗.................. 148
第六節 各藥材之指標成分抑菌試驗............................................................. 150
第五章 實驗部份……………………………………...………………………… 153
第一節 實驗所使用之儀器與藥品………...…………………………..…… 153
第二節 藥材之成分抽取與分離……………………………………....……. 154
2.1 五倍子…………………………………………………………... 154
2.2 丁香……………………………………...………………………... 154
2.3 肉桂…………………………………...…………………………... 155
2.4 虎杖……………………………………………………………... 155
2.5 大黃………………………………...……………………………... 156
第三節 藥材指標成分之定量分析……………………...………………….. 156
3.1 儲存標準液（standard stock solution）之配製………………...….. 156
3.2 標準品溶液之配製……………………………………...………... 157
3.3 檢液之配製………………………………………...……………... 158
3.4 鑑別試驗及含量測定……………………………..……………… 159
第四節 分析方法之評估…………………………….……………………… 159
第五節 抑菌活性實驗……………………………………...………….. 160
5.1 供試菌株……………………………………………………...…... 160
5.2 孢子懸浮液的製備……………………………………………...... 161
5.3 藥材粗萃物與各畫分對C. higginsianum PA-19孢子發芽的抑制 161
5.4 標準品對C. higginsianum PA-19孢子發芽的抑制……………… 161
參考文獻…………………………………………………………………………. 162
已發表期刊論文…………………………………………………………………. 180
研討會論文………………………………………………………………………. 187

表目錄

表1、辣木各分畫層對MCF-7/ADR細胞毒殺活性………………..…………... 2
表2、由辣木根皮純化所得之化合物相對含量………………….…………….. 32
表3、由辣木莖皮純化所得之化合物相對含量………………………………... 33
表4、由芝麻種子純化所得之化合物相對含量……………….……………….. 78
表5、芝麻木酚素類DPPH自由基捕捉活性試驗………..…………………….. 91
表6、芝麻木酚素類於濃度32.3 ~ 500.0 μM下超氧陰離子抑制活性……..…. 93
表7、芝麻木酚素類亞鐵離子螯合能力活性試驗………….………………….. 95
表8、芝麻木酚素類還原力活性試驗………………………….……………….. 97
表9、五倍子甲醇粗抽物與各分畫層之HPLC梯度沖提程式………………… 123
表10、沒食子酸及沒食子酸甲酯同日內及異日間分析之精密度…….........… 126
表11、回收率實驗結果……………………………………………………….… 127
表12、五倍子各分畫層中所含指標成分之含量 (%, g/g ) …………………… 129
表13、丁香酚同日內及異日間分析之精密度……………………………….… 132
表14、回收率實驗結果……………………………………………………….… 132
表15、丁香各分畫層中所含指標成分之含量 (%, g/g ) ……………………… 134
表16、肉桂醛同日內及異日間分析之精密度…….…………………………… 137
表17、回收率實驗結果…………………………………………………………. 137
表18、肉桂各分畫層中所含指標成分之含量 (%, g/g ) ……………………… 139
表19、五倍子之白菜炭疽菌抑菌結果…………………………………………. 141
表20、丁香之白菜炭疽菌抑菌結果……………………………………………. 143
表21、肉桂之白菜炭疽菌抑菌結果……………………………………………. 145
表22、虎杖之白菜炭疽菌抑菌結果……………………………………………. 147
表23、大黃之白菜炭疽菌抑菌結果……………………………………………. 149
表24、標準品及對照組之IC50濃度比較……………………………………….. 151



圖目錄

圖1、辣木之外觀圖............................................................................................... 3
圖2、辣木之小葉圖............................................................................................... 4
圖3、辣木之圓錐形花序圖................................................................................... 4
圖4、辣木之果莢圖............................................................................................... 4
圖5、辣木之種子圖............................................................................................... 4
圖6、辣木根皮之萃取分離流程........................................................................... 26
圖7、辣木根皮氯仿分畫層之分離流程............................................................... 27
圖8、辣木根皮水層分畫層之分離流程............................................................... 27
圖9、辣木莖皮之萃取分離流程........................................................................... 28
圖10、辣木莖皮氯仿分畫層之分離流程............................................................. 29
圖11、化合物（80）之H1-NMR 光譜………………………………..………….. 35
圖12、化合物（80）之C13-NMR及DEPT 光譜……………………..………….. 35
圖13、化合物（88）之H1-NMR 光譜…………………………………………… 37
圖14、化合物（88）之C13-NMR及DEPT 光譜………………………..……….. 37
圖15、化合物（88）之COSY光譜......................................................................... 38
圖16、化合物（88）之NOESY光譜……………………………………..………. 38
圖17、化合物（88）之HMQC光譜……………………………………………… 39
圖18、化合物（88）之HMBC光譜……………………………………..……….. 39
圖19、化合物（91）之H1-NMR 光譜…………………………………..……….. 41
圖20、化合物（91）之C13-NMR及DEPT 光譜………………………………… 41
圖21、化合物（91）之COSY光譜………………………………………….…… 42
圖22、化合物（91）之NOESY光譜………………………………………..……. 42
圖23、化合物（91）之HMQC光譜……………………………………..……….. 43
圖24、化合物（91）之HMBC光譜……………………………………………… 43
圖25、芝麻之花朵圖……………………………………………………….…… 61
圖26、芝麻之種子圖……………………………………………………….…… 61
圖27、芝麻之外觀繪圖…………………………………………………….…… 62
圖28、芝麻種子之萃取分離流程………………………….…………………… 74
圖29、芝麻種子己烷分畫層之分離流程……………………….……………… 74
圖30、芝麻種子乙酸乙酯分畫層之分離流程…………………….…………… 75
圖31、芝麻種子水分畫層之分離流程…………………………….…………… 75
圖32、化合物（152）之H1-NMR 光譜……………………………..…………… 81
圖33、化合物（152）之C13-NMR及DEPT 光譜…………………..…………… 81
圖34、化合物（152）之COSY光譜……………………………….…………...... 82
圖35、化合物（152）之NOESY光譜……………………………..……………... 82
圖36、化合物（152）之HMQC光譜………………………………..…………… 83
圖37、化合物（152）之HMBC光譜……………………………….……………. 83
圖38、化合物（153）之H1-NMR 光譜…………………………..……………… 85
圖39、芝麻木酚素類DPPH自由基捕捉活性試驗……………………..……… 91
圖40、芝麻木酚素類於濃度500.0 μM下超氧陰離子抑制活性試驗…..…….. 93
圖41、芝麻木酚素類於濃度32.3 μM下超氧陰離子抑制活性試驗.…………. 93
圖42、芝麻木酚素類亞鐵離子螯合能力活性試驗………………………….… 95
圖43、芝麻木酚素類還原力活性試驗…………………………………….…… 97
圖44、C. higginsianum繪圖.................................................................................. 114
圖45、左為葉片上的病徵；右為葉柄上的病徵................................................... 114
圖46、五倍子外觀圖............................................................................................. 115
圖47、丁香植物外觀圖......................................................................................... 116
圖48、丁香藥材外觀圖......................................................................................... 117
圖49、肉桂植物外觀圖......................................................................................... 118
圖50、肉桂藥材外觀圖......................................................................................... 118
圖51、虎杖植物外觀圖......................................................................................... 119
圖52、虎杖藥材外觀圖......................................................................................... 120
圖53、大黃植物外觀圖......................................................................................... 121
圖54、大黃藥材外觀圖......................................................................................... 121
圖55、沒食子酸標準品之HPLC層析圖.............................................................. 124
圖56、沒食子酸甲酯標準品之HPLC層析圖...................................................... 124
圖57、沒食子酸標準品檢量線............................................................................. 125
圖58、沒食子酸甲酯標準品檢量線..................................................................... 125
圖59、五倍子甲醇粗萃物之HPLC層析圖.......................................................... 128
圖60、五倍子乙酸乙酯層抽出物之HPLC層析圖.............................................. 128
圖61、五倍子水層抽出物之HPLC層析圖.......................................................... 129
圖62、丁香酚標準品之HPLC層析圖.................................................................. 130
圖63、丁香酚標準品檢量線................................................................................. 131
圖64、丁香甲醇粗萃物之HPLC層析圖.............................................................. 133
圖65、丁香乙酸乙酯層抽出物之HPLC層析圖.................................................. 133
圖66、丁香水層抽出物之HPLC層析圖.............................................................. 134
圖67、肉桂醛標準品之HPLC層析圖.................................................................. 135
圖68、肉桂醛標準品檢量線................................................................................. 136
圖69、肉桂甲醇粗萃物之HPLC層析圖.............................................................. 138
圖70、肉桂乙酸乙酯層抽出物之HPLC層析圖.................................................. 138
圖71、肉桂水層抽出物之HPLC層析圖.............................................................. 139
圖72、五倍子之白菜炭疽菌抑菌結果................................................................. 141
圖73、丁香之白菜炭疽菌抑菌結果..................................................................... 143
圖74、肉桂之白菜炭疽菌抑菌結果..................................................................... 145
圖75、虎杖之白菜炭疽菌抑菌結果..................................................................... 147
圖76、大黃之白菜炭疽菌抑菌結果..................................................................... 149
圖77、標準品及對照組之IC50比較...................................................................... 150
圖78、標準品及對照組之白菜炭疽菌抑菌結果................................................. 152

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