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研究生:伍怡瑾
研究生(外文):Yi-Chin Wu
論文名稱:穗花山奈根莖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 Rhizome of Hedychium coronarium
指導教授:陳日榮
指導教授(外文):Jih-Jung Chen
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:2011
畢業學年度:99
語文別:中文
論文頁數:133
中文關鍵詞:薑科穗花山奈根莖抗發炎活性hedychicoronarinperoxycoronarin D
外文關鍵詞:peroxycoronarin DZingiberaceaerhizomesHedychium coronariumanti-inflammatory activityhedychicoronarin
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中文摘要
穗花山奈為薑科之多年生草本植物,分布於印度、馬來西亞、越南、南中國及台灣。對台灣產植物進行抗發炎活性篩選,其中穗花山奈為活性植物之一。
由穗花山奈根莖之n-hexane可溶部,目前已分離出兩個新的labdane-type diterpenoids:hedychicoronarin (1)及peroxycoronarin D (2),以及十四個已知化合物 (3–16)。上述化合物之結構,經由各種圖譜分析及文獻數據比對予以確認。
目前分離得到的化合物中,calcaratarin (3), coronarin A (4), (E)-labda-8(17),12-diene-15,16-dial (8)及oleic acid (14)對於formyl-L- methionyl-L-leuckyl-L-phenylalanine/cytochalasin B (fMLP/CB)所誘導超氧陰離子的產生,具有良好的抑制活性(IC50 ≤ 3.31 g/mL)。此外,calcaratarin (3), coronarin A (4), (E)-labda-8(17),12-diene-15,16-dial (8), ergosta-4,6,8(14),22-tetraen-3-one (9)及oleic acid (14)對於fMLP/CB所誘導彈性蛋白酶的釋放,亦具有不錯的抑制作用(IC50 ≤ 6.17 g/mL)。
ABSTRACT
Hedychium coronarium Koenig (Zingiberaceae) is a perennial herb distributed in India, Malaysia, Vietnam, southern China, and Taiwan. In our studies on the anti-inflammatory constituents of Formosan plants, many species have been screened for in vitro anti-inflammatory activity, and H. coronarium has been found to be one of the active species.
The phytochemical investigation on the n-hexane-soluble fraction of the rhizomes of H. coronarium has led to the isolation of two new labdane diterpenoids, hedychicoronarin (1) and peroxycoronarin D (2), and fourteen known compounds (3–16). The structures of all isolates were determined through spectral analyses and comparison of their physical and spectral data with literatures.
Among the isolated compounds, calcaratarin (3), coronarin A (4), (E)-labda-8(17),12-diene-15,16-dial (8), and oleic acid (14) exhibited inhibition (IC50 ≤ 3.31 g/mL) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leuckyl-L-phenyl- alanine/cytochalasin B (fMLP/CB). In addition, calcaratarin (3), coronarin A (4), (E)-labda-8(17),12-diene-15,16-dial (8), ergosta-4,6, 8(14),22-tetraen-3-one (9), and oleic acid (14) inhibited fMLP/CB- induced elastase release with IC50 values ≤ 6.17 g/mL.
目 錄
頁次
第一章 緒言 1
第二章 研究動機與目的 3
第三章 薑科蝴蝶薑屬植物過去成分研究概要 5
第四章 抽出與分離 27
第五章 結果與討論 33
第一節 Hydychicoronarin (1)之結構研究 33
第二節 Peroxycoronarin D (2)之結構研究 42
第三節 Calcaratarin (3)之結構研究 50
第四節 Coronarin A (4)之結構研究 54
第五節 Coronarin D (5)之結構研究 58
第六節 Coronarin D methyl ether (6)之結構研究 62
第七節 Coronarin D ethyl ether (7)之結構研究 66
第八節 (E)-Labda-8(17),12-diene-15,16-dial (8)之結構研究 69
第八節 (E)-Labda-8(17),12-diene-15,16-dial (8)之結構研究 70
第九節 Ergosta-4,6,8(14),22-tetraen-3-one (9)之結構研究 74
第十節 -Sitostenone (10)與Stigmasta-4,22-dien-3-one (11)之結構研究 78
第十一節 6-Hydroxystigmast-4-en-3-one (12)與6-Hydroxystigmasta-4,22-dien-3-one (13)之結構研究 82
第十二節 Oleic acid (14)之結構研究 86
第十三節 Stearic acid (15)與Palmitic acid (16)之結構研究 89
第六章 抗發炎活性研究 92
第七章 結論 95
第八章 實驗部分 97
第一節 儀器與材料 97
第二節 穗花山奈根莖抽取與分離 99
第三節 抗發炎活性之實驗方法 102
第四節 各化合物之實驗數據 105
第九章 參考文獻 112
第十章 已發表之研究成果 120


圖 表 目 錄
頁次
圖A:Flower of Hedychium coronarium Koenig 2
圖B:Aerial part of Hedychium coronarium Koenig 2
Scheme A:穗花山奈根莖之分離流程 27
Scheme B:穗花山奈根莖n-hexane可溶部之成分分離 28
圖1-1:Hydychicoronarin (1)之ESI-MS圖譜 37
圖1-2:Hydychicoronarin (1)之HR-ESI-MS圖譜 37
圖1-3:Hydychicoronarin (1)之IR圖譜 38
圖1-4:Hydychicoronarin (1)之13C-NMR圖譜(CDCl3, 100 MHz) 38
圖1-5:Hydychicoronarin (1)之1H-NMR圖譜(CDCl3, 400 MHz) 39
圖1-6:Hydychicoronarin (1)之NOESY圖譜 39
圖1-7:Hydychicoronarin (1)之1H-1H COSY圖譜 40
圖1-8:Hydychicoronarin (1)之HMBC圖譜 40
圖1-9:Hydychicoronarin (1)之HSQC圖譜 41
圖1-10:Hydychicoronarin (1)之DEPT圖譜 41
圖2-1:Peroxycoronarin D (2)之ESI-MS圖譜 45
圖2-2:Peroxycoronarin D (2)之HR-ESI-MS圖譜 45
圖2-3:Peroxycoronarin D (2)之IR圖譜 46
圖2-4:Peroxycoronarin D (2)之13C-NMR圖譜(CDCl3, 100 MHz) 46
圖2-5:Peroxycoronarin D (2)之1H-NMR圖譜(CDCl3, 400 MHz) 47
圖2-6:Peroxycoronarin D (2)之NOESY圖譜 47
圖2-7:Peroxycoronarin D (2)之1H-1H COSY圖譜 48
圖2-8:Peroxycoronarin D (2)之HMBC圖譜 48
圖2-9:Peroxycoronarin D (2)之HSQC圖譜 49
圖2-10:Peroxycoronarin D (2)之DEPT圖譜 49
圖3-1:Calcaratarin (3)之ESI-MS圖譜 52
圖3-2:Calcaratarin (3)之IR圖譜 52
圖3-3:Calcaratarin (3)之1H-NMR圖譜(CDCl3, 600 MHz) 53
圖4-1:Coronarin A (4)之ESI-MS圖譜 56
圖4-2:Coronarin A (4)之IR圖譜 56
圖4-3:Coronarin A (4)之1H-NMR圖譜(CDCl3, 200 MHz) 57
圖5-1:Coronarin D (5)之ESI-MS圖譜 60
圖5-2:Coronarin D (5)之IR圖譜圖 60
圖5-3:Coronarin D (5)之1H-NMR圖譜(CDCl3, 200 MHz) 61
圖6-1:Coronarin D methyl ether (6)之ESI-MS圖譜 64
圖6-2:Coronarin D methyl ether (6)之IR圖譜 64
圖6-3:Coronarin D methyl ether (6)之1H-NMR圖譜(CDCl3, 400 MHz) 65
圖7-1:Coronarin D ethyl ether (7)之ESI-MS圖譜 68
圖7-2:Coronarin D ethyl ether (7)之IR圖譜 68
圖7-3:Coronarin D ethyl ether (7)之1H-NMR圖譜(CDCl3, 200 MHz) 69
圖8-1:(E)-Labda-8(17),12-diene-15,16-dial (8)之ESI-MS圖譜 72
圖8-2:(E)-Labda-8(17),12-diene-15,16-dial (8)之IR圖譜 72
圖8-3:(E)-Labda-8(17),12-diene-15,16-dial (8)之1H-NMR圖譜 (CDCl3, 200 MHz) 73
圖9-1:Ergosta-4,6,8(14),22-tetraen-3-one (9)之ESI-MS圖 76
圖9-2:Ergosta-4,6,8(14),22-tetraen-3-one (9)之IR圖譜 76
圖9-3:Ergosta-4,6,8(14),22-tetraen-3-one (9)之1H-NMR圖譜 (CDCl3, 500 MHz) 77
圖10-1:-Sitostenone (10)與Stigmasta-4,22-dien-3-one (11)之 ESI-MS圖譜 80
圖10-2:-Sitostenone (10)與Stigmasta-4,22-dien-3-one (11)之 IR圖譜 80
圖10-3:-Sitostenone (10)與Stigmasta-4,22-dien-3-one (11)之 1H-NMR圖譜(CDCl3, 200 MHz) 81
圖11-1:6-Hydroxystigmast-4-en-3-one (12)與6-Hydroxystigmasta- 4,22-dien-3-one (13)之ESI-MS圖譜 84
圖11-2:6-Hydroxystigmast-4-en-3-one (12)與6-Hydroxystigmasta- 4,22-dien-3-one (13)之IR圖譜 84
圖11-3:6-Hydroxystigmast-4-en-3-one (12)與6-Hydroxystigmasta- 4,22-dien-3-one (13)之1H-NMR圖譜(CDCl3, 200 MHz) 85
圖12-1:Oleic acid (14)之ESI-MS圖譜 87
圖12-2:Oleic acid (14)之IR圖譜 87
圖12-3:Oleic acid (14)之1H-NMR圖譜(CDCl3, 400 MHz) 88
圖13-1:Stearic acid (15)與Palmitic acid (16)之ESI-MS圖譜 90
圖13-2:Stearic acid (15)與Palmitic acid (16)之IR圖譜 90
圖13-3:Stearic acid (15)與Palmitic acid (16)之1H-NMR圖譜 (CDCl3, 200 MHz) 91
表1:薑科蝴蝶薑屬(Hedychium)植物過去分離之化學成分 14
表2:化合物之抗發炎活性 94
第九章 參考文獻
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