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研究生:黃聖秀
研究生(外文):Sheng-Shiou Huang
論文名稱:大葉桃花心木果實之化學成分及抗發炎活性之研究
論文名稱(外文):Studies on the Chemical Constituents and Anti-inflammatory Activities from the Fruit of Swietenia macrophylla
指導教授:陳日榮魏道昌魏道昌引用關係
學位類別:碩士
校院名稱:大仁科技大學
系所名稱:製藥科技研究所
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:2009
畢業學年度:97
語文別:中文
論文頁數:133
中文關鍵詞:桃花心木屬抗發炎大葉桃花心木果實棟科
外文關鍵詞:anti-inflammatoryFruitMeliaceaeSwietenia macrophyllaSwietenia
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大葉桃花心木為楝科之常綠大喬木,分佈於美洲熱帶地區,主要在宏都拉斯、墨西哥、玻利維亞及中美洲一帶。對台灣產植物進行抗發炎活性篩選,發現大葉桃花心木果實具有抗發炎活性。
由大葉桃花木果實之EtOAc可溶部,目前已分離出一個新的phra- gmalin-type limonoid: 6-O-acetyl-3′-demethylswietephragmin E (1),及十六個已知化合物。十六個已知化合物包括十個limonoids: swietenine (2), swietenine acetate (3), febrifugin (4), 3,6-O,O-diacetyl swietenolide (5), 3-O-tigloylswietenolide (6), khayasin T (7), 3-O-tigloyl-6-O-acetylswiete- nolide (8), swietemahonin E (9), 6-O-acetylswietemahonin G (10), 2- hydroxyswietemahonolide (11),一個coumarin: scopoletin (12),四個steroids: β-sitostenone (13), 3β-hydroxystigmast-5-en-7-one (14), 及 β- sitosterol (15)與 stigmasterol (16)的混合物,以及一個 fatty acid ester: stearic acid methyl ester (17)。上述各化合物之結構,經由各種圖譜分析及文獻數據比對予以確認。
目前分離所得到的化合物中,6-O-acetyl-3′-demethylswietephrag- min E (1), 3,6-O,O-diacetylswietenolide (5), 3-O-tigloylswietenolide (6), 3-O-tigloyl-6-O-acetylswietenolide (8), swietemahonin E (9)及6-O- acetylswietemahonin G (10)對於formyl-L-methionyl-L-leuckyl-L-phenyl-alanine (fMLP)誘導人類嗜中性白血球產生超氧陰離子(O2•–),具有良好的抑制活性(IC50 ≤ 35.71 μM)。
Swietenia macrophylla King (Meliaceae) is a tropical timber tree, natively distributed throughout tropical regions of the Americas, mainly in Honduras, Mexico, Bolivia, and Central America. In our studies on the anti-inflammatory constituents of Formosan plants, many species have been screened for in vitro inhibitory activity on neutrophil pro- inflammatory responses, and S. macrophylla has been found to be an active species.
In our search for compounds with anti-inflammatory activities, a new phragmalin-type limonoid, 6-O-acetyl-3′-demethylswietephragmin E (1) and 16 known compounds (2–17) have been isolated and identified from the fruits of S. macrophylla. Sixteen known compounds include ten limonoids, swietenine (2), swietenine acetate (3), febrifugin (4), 3,6-O,O- diacetylswietenolide (5), 3-O-tigloylswietenolide (6), khayasin T (7), 3-O- tigloyl-6-O-acetylswietenolide (8), swietemahonin E (9), 6-O-acetylswie- temahonin G (10), and 2-hydroxyswietemahonolide (11), a coumarin, scopoletin (12), four steroids, β-sitostenone (13), 3β-hydroxystigmast- 5-en-7-one (14), and a mixture of β-sitosterol (15) and stigmasterol (16), and a fatty acid ester, stearic acid methyl ester (17). The structures of above isolates were determined through spectral analyses and comparison of their physical and spectral data with literatures.
Among the isolated compounds, 6-O-acetyl-3′-demethylswietephrag- min E (1), 3,6-O,O-diacetylswietenolide (5), 3-O-tigloylswietenolide (6), 3-O-tigloyl-6-O-acetylswietenolide (8), swietemahonin E (9), and 6-O- acetylswietemahonin G (10) exhibited inhibition (IC50 ≤ 35.71 μM) of superoxide anion generation by human neutrophils in response to formyl- L-methionyl-L-leucyl-L-phenylalanine (fMLP).
目 錄
頁次
中文摘要 1
Abstract 3
第一章 緒言 6
第二章 研究動機與目的 7
第三章 過去化學成分研究概要 9
第四章 抽出與分離 31
第五章 結果與討論 38
第一節 6-O-Acetyl-3-demethylswietephragmin E (1)之結構研究 38
第二節 Swietenine (2)之結構研究 49
第三節 Swietenine acetate (3)之結構研究 52
第四節 Febrifugin (4)之結構研究 55
第五節 3,6-O,O-Diacetylswietenolide (5)之結構研究 58
第六節 3-O-Tigloylswietenolide (6)之結構研究 61
第七節 Khayasin T (7)之結構研究 64
第八節 3-O-Tigloyl-6-O-acetylswietenolide (8)之結構研究 67
第九節 Swietemahonin E (9)之結構研究 70
第十節 6-O-Acetylswietemahonin G (10)之結構研究 73
第十一節 2-Hydroxyswietemahonolide (11)之結構研究 76
第十二節 Scopoletin (12)之結構研究 79
第十三節 -Sitostenone (13)之結構研究 82
第十四節 3-Hydroxystigmast-5-en-7-one (14)之結構研究 85
第十五節 混合物-Sitosterol (15)與Stigmasterol (16)之結構研究 88
第十六節 Stearic acid methyl ester (17)之結構研究 91
第六章 抗發炎活性研究 94
第七章 結論 97
第八章 實驗部分 98
第一節 儀器與材料 98
第二節 大葉桃花心木果實之抽取與分離 100
第三節 抗發炎活性之實驗方法 103
第四節 化合物之實驗數據 105
第九章 參考文獻 113
第十章 已發表之研究成果 121
圖 表 目 錄
頁次
圖A: 大葉桃花心木...................................................................................5
圖B: 大葉桃花心木....................................................................................5
圖C: 大葉桃花心木果實分離之流程圖..................................................31
圖D: 大葉桃花心木果實EtOAc可溶部之成分分離............................32
圖 1-1: 6-O-Acetyl-3′-demethylswietephragmin E (1)之ESI-MS 圖譜..............................................................................................43
圖 1-2: 6-O-Acetyl-3′-demethylswietephragmin E (1)之HR-ESI-MS 圖譜................................................................................................43
圖 1-3: 6-O-Acetyl-3′-demethylswietephragmin E (1)之IR圖譜...........44
圖 1-4: 6-O-Acetyl-3′-demethylswietephragmin E (1)之1H-NMR 圖譜................................................................................................44
圖 1-5: 6-O-Acetyl-3′-demethylswietephragmin E (1)之NOESY 圖譜................................................................................................45
圖 1-6: 6-O-Acetyl-3′-demethylswietephragmin E (1)之HMBC 圖譜................................................................................................45
圖 1-7: 6-O-Acetyl-3′-demethylswietephragmin E (1)之HSQC圖譜....46
圖 1-8: 6-O-Acetyl-3′-demethylswietephragmin E (1)之DEPT圖譜.....46
III
圖 1-9: 6-O-Acetyl-3′-demethylswietephragmin E (1)之13C-NMR 圖譜................................................................................................47
圖 1-10: 6-O-Acetyl-3′-demethylswietephragmin E (1)之1H-1H COSY 圖譜..............................................................................................47
圖 1-11: 6-O-Acetyl-3′-demethylswietephragmin E (1)之電腦輔助3D模擬相對立體構型及選擇性NOESY correlation.........................48
圖 2-1: Swietenine (2)之ESI-MS圖譜....................................................50
圖 2-2: Swietenine (2)之IR圖譜.............................................................51
圖 2-3: Swietenine (2)之1H-NMR圖譜...................................................51
圖 3-1: Swietenine acetate (3)之ESI-MS圖譜........................................53
圖 3-2: Swietenine acetate (3)之IR圖譜.................................................54
圖 3-3: Swietenine acetate (3)之1H-NMR圖譜.......................................54
圖 4-1: Febrifugin (4)之ESI-MS圖譜.....................................................56
圖 4-2: Febrifugin (4)之IR圖譜..............................................................57
圖 4-3: Febrifugin (4)之1H-NMR圖譜....................................................57
圖 5-1: 3,6-O,O-Diacetylswietenolide (5)之ESI-MS圖譜......................59
圖 5-2: 3,6-O,O-Diacetylswietenolide (5)之IR圖譜...............................60
圖 5-3: 3,6-O,O-Diacetylswietenolide (5)之1H-NMR圖譜....................60
圖 6-1: 3-O-Tigloylswietenolide (6)之ESI-MS圖譜...............................62
IV
圖 6-2: 3-O-Tigloylswietenolide (6)之IR圖譜........................................63
圖 6-3: 3-O-Tigloylswietenolide (6) 之1H-NMR圖譜...........................63
圖 7-1: Khayasin T (7)之ESI-MS圖譜....................................................65
圖 7-2: Khayasin T (7)之IR圖譜.............................................................66
圖 7-3: Khayasin T (7)之1H-NMR圖譜..................................................66
圖 8-1: 3-O-Tigloyl-6-O-acetylswietenolide (8)之ESI-MS圖譜............68
圖 8-2: 3-O-Tigloyl-6-O-acetylswietenolide (8)之IR圖譜.....................69
圖 8-3: 3-O-Tigloyl-6-O-acetylswietenolide (8)之1H-NMR圖譜..........69
圖 9-1: Swietemahonin E (9)之ESI-MS圖譜..........................................71
圖 9-2: Swietemahonin E (9)之IR圖譜...................................................72
圖 9-3: Swietemahonin E (9)之1H-NMR圖譜........................................72
圖 10-1: 6-O-Acetylswietemahonin G (10)之ESI-MS圖譜....................74
圖 10-2: 6-O-Acetylswietemahonin G (10)之IR圖譜.............................75
圖 10-3: 6-O-Acetylswietemahonin G (10)之1H-NMR圖譜...................75
圖 11-1: 2-Hydroxyswietemahonolide (11)之ESI-MS圖譜....................77
圖 11-2: 2-Hydroxyswietemahonolide (11)之IR圖譜.............................78
圖 11-3: 2-Hydroxyswietemahonolide (11)之1H-NMR圖譜..................78
圖 12-1: Scopoletin (12)之ESI-MS圖譜.................................................80
圖 12-2: Scopoletin (12)之IR圖譜..........................................................80
V
圖 12-3: Scopoletin (12)之1H-NMR圖譜...............................................81
圖 13-1: β-Sitostenone (13)之ESI-MS圖譜............................................83
圖 13-2: β-Sitostenone (13)之IR圖譜.....................................................83
圖 13-3: β-Sitostenone (13)之1H-NMR圖譜..........................................84
圖 14-1: 3β-Hydroxystigmast-5-en-7-one (14)之ESI-MS圖譜..............86
圖 14-2: 3β-Hydroxystigmast-5-en-7-one (14)之IR圖譜.......................86
圖 14-3: 3β-Hydroxystigmast-5-en-7-one (14)之1H-NMR圖譜............87
圖 15-1: β-Sitosterol (15)與Stigmasterol (16)之EI-MS圖譜................89
圖 15-2: β-Sitosterol (15)與Stigmasterol (16)之IR圖譜.......................90
圖 15-3: β-Sitosterol (15)與Stigmasterol (16)之1H-NMR圖譜.............90
圖 16-1: Stearic acid methyl ester (17)之ESI-MS圖譜...........................92
圖 16-2: Stearic acid methyl ester (17)之IR圖譜....................................92
圖 16-3: Stearic acid methyl ester (17)之1H-NMR圖譜.........................93
表1. 桃花心木屬(Swietenia)植物過去分離之化學成分及文獻............15
表2. 化合物1之1H-NMR數據..............................................................41
表3. 化合物1之13C-NMR數據.............................................................42
表4. 化合物之抗發炎活性......................................................................96
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